WO2004105150A1 - Hole transport composition - Google Patents
Hole transport composition Download PDFInfo
- Publication number
- WO2004105150A1 WO2004105150A1 PCT/US2004/016409 US2004016409W WO2004105150A1 WO 2004105150 A1 WO2004105150 A1 WO 2004105150A1 US 2004016409 W US2004016409 W US 2004016409W WO 2004105150 A1 WO2004105150 A1 WO 2004105150A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition according
- ether
- acid
- layer
- alcohol
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 62
- 230000005525 hole transport Effects 0.000 title description 4
- 239000002184 metal Substances 0.000 claims abstract description 44
- 229910052751 metal Inorganic materials 0.000 claims abstract description 44
- 229920001940 conductive polymer Polymers 0.000 claims abstract description 31
- 150000001768 cations Chemical class 0.000 claims abstract description 25
- 239000006184 cosolvent Substances 0.000 claims abstract description 24
- 150000002739 metals Chemical class 0.000 claims abstract description 10
- -1 cyano, hydroxyl Chemical group 0.000 claims description 64
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 46
- 239000000872 buffer Substances 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 claims description 12
- RZXLPPRPEOUENN-UHFFFAOYSA-N Chlorfenson Chemical compound C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 RZXLPPRPEOUENN-UHFFFAOYSA-N 0.000 claims description 11
- 239000004593 Epoxy Substances 0.000 claims description 11
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 11
- 150000007942 carboxylates Chemical class 0.000 claims description 11
- 150000001450 anions Chemical class 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 9
- 125000002723 alicyclic group Chemical group 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229920000767 polyaniline Polymers 0.000 claims description 9
- 229920000123 polythiophene Polymers 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 229910000077 silane Inorganic materials 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 8
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000001589 carboacyl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 229920000128 polypyrrole Polymers 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical group CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 7
- 125000004450 alkenylene group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 6
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- ZAHSNWXGKUBLHM-UHFFFAOYSA-N hydroperoxy(hydroxy)silane Chemical compound OO[SiH2]O ZAHSNWXGKUBLHM-UHFFFAOYSA-N 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 150000001735 carboxylic acids Chemical group 0.000 claims description 5
- 230000005855 radiation Effects 0.000 claims description 5
- 239000004065 semiconductor Substances 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 150000004292 cyclic ethers Chemical class 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical group 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 150000003568 thioethers Chemical class 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 125
- 230000007547 defect Effects 0.000 description 35
- 239000000463 material Substances 0.000 description 28
- 239000002904 solvent Substances 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000002253 acid Substances 0.000 description 15
- 229920000144 PEDOT:PSS Polymers 0.000 description 12
- 239000000654 additive Substances 0.000 description 11
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 229910001415 sodium ion Inorganic materials 0.000 description 9
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 238000011084 recovery Methods 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 239000002322 conducting polymer Substances 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000005240 physical vapour deposition Methods 0.000 description 6
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 6
- 238000010998 test method Methods 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 5
- 229910052788 barium Inorganic materials 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000005229 chemical vapour deposition Methods 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 3
- HTSABYAWKQAHBT-UHFFFAOYSA-N 3-methylcyclohexanol Chemical compound CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 3
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
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- 125000001153 fluoro group Chemical group F* 0.000 description 3
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- 238000012360 testing method Methods 0.000 description 3
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- 238000012546 transfer Methods 0.000 description 3
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- 150000007513 acids Chemical class 0.000 description 2
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- 229910052783 alkali metal Inorganic materials 0.000 description 2
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- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
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- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
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- AILKHAQXUAOOFU-UHFFFAOYSA-N hexanenitrile Chemical compound CCCCCC#N AILKHAQXUAOOFU-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 238000009616 inductively coupled plasma Methods 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 238000001659 ion-beam spectroscopy Methods 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 1
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- HEBMCVBCEDMUOF-UHFFFAOYSA-N isochromane Chemical compound C1=CC=C2COCCC2=C1 HEBMCVBCEDMUOF-UHFFFAOYSA-N 0.000 description 1
- QHDRKFYEGYYIIK-UHFFFAOYSA-N isovaleronitrile Chemical compound CC(C)CC#N QHDRKFYEGYYIIK-UHFFFAOYSA-N 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000001755 magnetron sputter deposition Methods 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000002488 metal-organic chemical vapour deposition Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- GQKZBCPTCWJTAS-UHFFFAOYSA-N methoxymethylbenzene Chemical compound COCC1=CC=CC=C1 GQKZBCPTCWJTAS-UHFFFAOYSA-N 0.000 description 1
- VNKYTQGIUYNRMY-UHFFFAOYSA-N methoxypropane Chemical compound CCCOC VNKYTQGIUYNRMY-UHFFFAOYSA-N 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- YPEWWOUWRRQBAX-UHFFFAOYSA-N n,n-dimethyl-3-oxobutanamide Chemical compound CN(C)C(=O)CC(C)=O YPEWWOUWRRQBAX-UHFFFAOYSA-N 0.000 description 1
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- SDLAKRCBYGZJRW-UHFFFAOYSA-N n-tert-butylformamide Chemical compound CC(C)(C)NC=O SDLAKRCBYGZJRW-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002891 organic anions Chemical group 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- XIPFMBOWZXULIA-UHFFFAOYSA-N pivalamide Chemical compound CC(C)(C)C(N)=O XIPFMBOWZXULIA-UHFFFAOYSA-N 0.000 description 1
- JAMNHZBIQDNHMM-UHFFFAOYSA-N pivalonitrile Chemical compound CC(C)(C)C#N JAMNHZBIQDNHMM-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000007764 slot die coating Methods 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 238000003631 wet chemical etching Methods 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/124—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/026—Wholly aromatic polyamines
- C08G73/0266—Polyanilines or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0605—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0611—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring, e.g. polypyrroles
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
- H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
- H01B1/128—Intrinsically conductive polymers comprising six-membered aromatic rings in the main chain, e.g. polyanilines, polyphenylenes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/805—Electrodes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
Definitions
- the invention relates to an aqueous hole transport composition, and to devices comprising buffer layers including such compositions.
- Electrode devices such as organic light emitting diodes (OLEDs) containing conducting polymers
- OLEDs organic light emitting diodes
- the anode is typically any material that is transparent and has the ability to inject holes into the EL material, such as, for example, indium/tin oxide (ITO).
- ITO indium/tin oxide
- the anode is optionally supported on a glass or plastic substrate.
- EL materials include fluorescent dyes, fluorescent and phosphorescent metal complexes, conjugated polymers, and mixtures thereof.
- the cathode is typically any material (s uch as, e.g., Ca or Ba) that has the ability to inject electrons into the EL material.
- the buffer layer typically includes an electrically conducting polymer and facilitates the injection of holes from the anode into the EL material layer.
- Typical conducting polymers employed as buffer layers include polyaniline (“PAni”) and polydioxythiophenes such as poly(3,4- ethylenedioxythiophene) (“PEDT”). These materials can be prepared by polymerizing aniline or dioxythiophene monomers in aqueous solution in the presence of a water soluble polymeric acid, such as poly(styrenesulfonic acid) (PSSA), or poly(2-acrylamido-2-methyl-1- propanesulfonic acid) (“PAAMPSA”), as described in, for example, U.S. Patent No.
- PSSA poly(styrenesulfonic acid)
- PAAMPSA poly(2-acrylamido-2-methyl-1- propanesulfonic acid)
- New aqueous compositions comprising at least one doped conductive polymer, at least one co-solvent, and at least one metal cation selected from Group 1 metals or Group 2 metals or mixtures thereof.
- electronic devices comprising a buffer layer comprises the new composition.
- FIG. 1 illustrates a cross-sectional view of an electronic device that comprises a buffer layer comprises the new composition.
- aqueous compositions comprising at least one doped conductive polymer, at least one co-solvent, and at least one metal cation selected from Group 1 metals or Group 2 metals, and mixtures thereof.
- aqueous refers to a liquid that has a significant portion of water, and in one embodiment it is at least about 40% by weight water.
- doped refers to the formation of an ion pair wherein the negative charge on an anion balances the positive charge on a conductive polymer.
- the anion is referred to as a "dopant”.
- co-solvent refers to an organic substance which is liquid at room temperature and is miscible with water.
- miscible means that the co-solvent is capable of being mixed with water (at the concentration used) to form a substantially homogeneous solution.
- the IUPAC number system is used throughout, where the groups from the Periodic Table are numbered from left to right as 1-18 (CRC Handbook of Chemistry and Physics, 81 st Edition, 2000).
- the conductive polymers suitable for the new composition can be homopolymers, or they can be co-polymers of two or more respective monomers.
- the composition may further comprise one or more different conductive polymers.
- the conductive polymer is selected from polythiophenes, or polypyrroles, or polyanilines, or combinations thereof.
- Polythiophenes contemplated for use in the new composition comprise Formula I below:
- R 1 is independently selected so as to be the same or different at each occurrence and is selected from hydrogen, alkyl, alkenyl, alkoxy, alkanoyl, alkythio, aryloxy, alkylthioalkyl, alkylaryl, arylalkyl, amino, alkylamino, dialkylamino, aryl, alkylsulfinyl, alkoxyalkyl, alkylsulfonyl, arylthio, arylsulfinyl, alkoxycarbonyl, arylsulfonyl, acrylic acid, phosphoric acid, phosphonic acid, halogen, nitro, cyano, hydroxyl, epoxy, silane, siloxane, alcohol, benzyl, carboxylate, ether, amidosulfonate, ether carboxylate, ether sulfonate, and urethane; or both R 1 groups together may form an alkylene or alkenylene chain completing a 3,
- alkyl refers to a group derived from an aliphatic hydrocarbon and includes linear, branched and cyclic groups which may be unsubstituted or substituted.
- heteroalkyl is intended to mean an alkyl group, wherein one or more of the carbon atoms within the alkyl group has been replaced by another atom, such as nitrogen, oxygen, sulfur, and the like.
- alkylene refers to an alkyl group having two points of attachment.
- alkenyl refers to a group derived from an aliphatic hydrocarbon having at least one carbon-carbon double bond, and includes linear, branched and cyclic groups which may be unsubstituted or substituted.
- heteroalkenyl is intended to mean an alkenyl group, wherein one or more of the carbon atoms within the alkenyl group has been replaced by another atom, such as nitrogen, oxygen, sulfur, and the like.
- alkenylene refers to an alkenyl group having two points of attachment.
- R 3 is a single bond or an alkylene group
- R 4 is an alkylene group
- R 5 is an alkyl group
- R 6 is hydrogen or an alkyl group
- Z is H, alkali metal, alkaline earth metal, N(R 5 ) 4 or R 5
- any of the above groups may further be unsubstituted or substituted, and any group may have fluorine substituted for one or more hydrogens, including perfluorinated groups.
- both R 1 together form -O- (CHY)m-0- , where m is 2 or 3, and Y is the same or different at each occurrence and is selected from hydrogen, alkyl, alcohol, amidosulfonate, benzyl, carboxylate, ether, ether carboxylate, amidosulfonate, ether sulfonate, and urethane.
- all Y are hydrogen.
- the polythiophene is poly(3,4-ethylenedioxythiophene).
- at least one Y group is not hydrogen.
- at least one Y group is a substituent having fluorine substituted for at least one hydrogen.
- at least one Y group is perfluorinated.
- Polypyrroles contemplated for use the new composition comprise Formula II below. where in Formula II: n is at least about 4;
- R 1 is independently selected so as to be the same or different at each occurrence and is selected from hydrogen, alkyl, alkenyl, alkoxy, alkanoyl, alkythio, aryloxy, alkylthioalkyl, alkylaryl, arylalkyl, amino, alkylamino, dialkylamino, aryl, alkylsulfinyl, alkoxyalkyl, alkylsulfonyl, arylthio, arylsulfinyl, alkoxycarbonyl, arylsulfonyl, acrylic acid, phosphoric acid, phosphonic acid, halogen, nitro, cyano, hydroxyl, epoxy, silane, siloxane, alcohol, benzyl, carboxylate, ether, ether carboxylate, amidosulfonate, ether sulfonate, and urethane; or both R 1 groups together may form an alkylene or alkenylene chain completing a 3,
- R 1 is the same or different at each occurrence and is independently selected from hydrogen, alkyl, alkenyl, alkoxy, cycloalkyl, cycloalkenyl, alcohol, benzyl, carboxylate, ether, amidosulfonate, ether carboxylate, ether sulfonate, urethane, epoxy, silane, siloxane, and alkyl substituted with one or more of sulfonic acid, carboxylic acid, acrylic acid, phosphoric acid, phosphonic acid, halogen, nitro, cyano, hydroxyl, epoxy, silane, or siloxane moieties.
- R 2 is selected from hydrogen, alkyl, and alkyl substituted with one or more of sulfonic acid, carboxylic acid, acrylic acid, phosphoric acid, phosphonic acid, halogen, cyano, hydroxyl, epoxy, silane, or siloxane moieties.
- the polypyrrole is unsubstituted and both R 1 and R 2 are hydrogen.
- both R 1 together form a 6- or 7-membered alicyclic ring, which is further substituted with a group selected from alkyl, heteroalkyl, alcohol, benzyl, carboxylate, ether, ether carboxylate, amidosulfonate, ether sulfonate, and urethane. These groups can improve the solubility of the monomer and the resulting polymer.
- both R 1 together form a 6- or 7-membered alicyclic ring, which is further substituted with an alkyl group.
- both R 1 together form a 6- or 7-membered alicyclic ring, which is further substituted with an alkyl group having at least 1 carbon atom.
- both R 1 together form -0-(CHY)m-0- , where m is 2 or 3, and Y is the same or different at each occurrence and is selected from hydrogen, alkyl, alcohol, benzyl, carboxylate, ether, ether carboxylate, amidosulfonate, ether sulfonate, and urethane.
- at least one Y group is not hydrogen.
- at least one Y group is a substituent having fluorine substituted for at least one hydrogen.
- at least one Y group is perfluorinated.
- Polyanilines contemplated for use in the new composition comprise Formula III or Formula IV below.
- the conductive polymer is made by oxidative polymerization of the monomer or monomers to form the conductive polymer, in the presence of a soluble acid.
- the acid can be a polymeric or non-polymeric acid.
- the polymerization is generally carried out in a homogeneous solution. In one embodiment, the polymerization is carried out in a homogeneous aqueous solution. In another embodiment, the polymerization for obtaining the electrically conducting polymer is carried out in an emulsion of water and an organic solvent. In general, some water is present in order to obtain adequate solubility of the oxidizing agent and/or catalyst.
- Oxidizing agents such as ammonium persulfate, sodium persulfate, potassium persulfate, and the like, can be used.
- a catalyst such as ferric chloride, or ferric sulfate may also be present.
- the resulting polymerized product will be a solution, dispersion, or emulsion of the doped conductive polymer.
- Aqueous dispersions of polypyrrole and a non-polymeric organic acid anion are available commercially from Sigma- Aldrich (St. Louis, MO).
- Aqueous dispersions of poly(2,3- ethylendioxythiophene)/PSSA are available commercially from H.C. Starck, GmbH. (Leverkusen, Germany).
- Aqueous dispersions of doped polyaniline are available commercially from Covion Organic Semiconductors GmbH (Frankfurt, Germany) or Ormecon (Ambersbek, Germany).
- the polythiophene and polypyrrole polymers formed by oxidative polymerization are positively charged.
- In the conductive form of polyaniline at least some of the nitrogens are protonated, so that it also is positively charged.
- the positive charges are balanced by the negative charge of the dopant.
- the dopant is an organic anion.
- the dopant is an organic acid anion.
- the organic acid can be polymeric or non-polymeric.
- the acids are selected to be soluble in the polymerization medium for the conductive polymer, and accordingly, can be water-soluble or organic solvent soluble.
- the acid anions can be selected from sulfonates, carboxylates, phosphates, phosphonates, acrylates, and mixtures thereof.
- the acid is a sulfonic acid.
- the acid is a water-soluble acid or organic-soluble acid selected from a non-polymeric organic acid, a water soluble polymeric acid, and combinations thereof.
- polymeric organic acids include, but are not limited to, poly(styrenesulfonic acid) (PSSA), and poly(2-acrylamido-2-methyl-1- propanesulfonic acid) (“PAAMPSA”).
- PSSA poly(styrenesulfonic acid)
- PAAMPSA poly(2-acrylamido-2-methyl-1- propanesulfonic acid)
- PSS poly(styrenesulfonic acid)
- PAAMPSA poly(2-acrylamido-2-methyl-1- propanesulfonic acid)
- suitable non- polymeric acids include, but are not limited to, acetic acid, p- toluenesulfonic acid, camphorsulfonic acid, p-dodecylbenzenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, and the like.
- the corresponding acid anions are acetate, p-toluenesulfonate, camphorsulfonate, p-dodecylbenzenesulfonate, methanesulfonate, and trifluoromethanesulfonate. Mixtures of acid anions can be used.
- the combination of the positively charged conductive polymer and the anion is referred to as the "doped conductive polymer.”
- Aqueous dispersions of electrically conducting polymers which typically have a high surface energy of 73 mili-newton/meter, frequently form thin layers with coating inhomogeneity when spin-coated on an indium/tin oxide surface.
- films made from Baytron-P CH8000 or AI4083 which are aqueous dispersions of electrically conductive poly(3,4-ethylendioxythiophene)/PSSA available commercially from H.C. Starck, GmbH. (Leverkusen, Germany), are known to have coating defects, such as streaks, speed boats, mottles and/or bubbles.
- the new aqueous compositions of the invention form films having improved coating homogeneity.
- Co-solvents contemplated for use in the new composition are generally polar, water-miscible organic liquids.
- suitable types of co-solvents include, but are not limited to, ethers, cyclic ethers, alcohols, alcohol ethers, ketones, nitriles, sulfides, sulfoxides, amides, amines, carboxylic acids, as well as combinations of any two or more thereof.
- Exemplary ether co-solvents contemplated for use in the new composition include, but are not limited to, diethyl ether, ethyl propyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, methyl t-butyl ether, glyme, diglyme, benzyl methyl ether, isochroman, 2-phenylethyl methyl ether, n- butyl ethyl ether, 1 ,2-diethoxyethane, sec-butyl ether, diisobutyl ether, ethyl n-propyl ether, ethyl isopropyl ether, n-hexyl methyl ether, n-butyl methyl ether, methyl n-propyl ether, and the like, as well as combinations of any two or more thereof.
- Exemplary cyclic ether co-solvents contemplated for use in the new composition include, but are not limited to, 1 ,4-dioxane, tetrahydrofuran, tetrahydropyran, 4 methyl-1 ,3-dioxane, 4-phenyl-1 ,3-dioxane, 1 ,3- dioxolane, 2-methyl-1 ,3-dioxolane, 1 ,3-dioxane, 2,5- dimethoxytetrahydrofuran, 2,5-dimethoxy-2,5-dihydrofuran, and the like, as well as combinations of any two or more thereof.
- the cyclic ether co-solvent is tetrahydrofuran, tetrahydropyran, or 1 ,4- dioxane.
- exemplary alco.hol co-solvents contemplated for use in the new composition include, but are not limited to, methanol, ethanol, 1-propanol, 2-propanol (i.e., isopropanol), 1-butanol, 2-butanol, 2-methyl-1-propanol (i.e., isobutanol), 2-methyl-2-propanol (i.e., te/f-butanol), 1-pentanol, 2- pentanol, 3-pentanol, 2,2-dimethyl-1-propanol, 1-hexanol, cyclopentanol, 3-methyl-1-butanol, 3-methyl-2-butanol, 2-methyl-1-butanol, 2,2-dimethyl- 1-propanol, 3-hexanol,
- the alcohol co-solvent is methanol, ethanol, or isopropanol.
- Exemplary alcohol ether co-solvents contemplated for use in the new composition include, but are not limited to, 2-butoxyethanol, 1- methoxy-2-propanol, 2-methoxyethanol, 2-ethoxyethanol, 1-methoxy-2- butanol, ethylene glycol monoisopropyl ether, 1-ethoxy-2-propanol, 3- methoxy-1-butanol, ethylene glycol monoisobutyl ether, ethylene glycol mono-n-butyl ether, 3-methoxy-3-methylbutanol, ethylene glycol mono- tetf-butyl ether, and the like, as well as combinations of any two or more thereof.
- the alcohol ether co-solvent is 1-methoxy-2- propanol, 2-methoxyethanol, or 2-butoxyethanol.
- Exemplary ketone co-solvents contemplated for use in the new composition include, but are not limited to, acetone, methylethyl ketone, methyl iso-butyl ketone, cyclohexanone, isopropyl methyl ketone, 2- pentanone, 3-pentanone, 3-hexanone, diisopropyl ketone, 2-hexanone, cyclopentanone, 4-heptanone, iso-amyl methyl ketone, 3-heptanone, 2- heptanone, 4-methoxy-4-methyl-2-pentanone, 5-methyl-3-heptanone, 2- methylcyclohexanone, diisobutyl ketone, 5-methyl-2-octanone, 3- methylcyclohexanone, 2-cyclohexen-1-one, 4-methylcyclohexanone, cycloheptanone, 4-tert-butylcyclohexanone, isophorone,
- Exemplary nitrile co-solvents contemplated for use in the new composition include, but are not limited to, acetonitrile, acrylonitrile, trichloroacetonitrile, propionitrile, pivalonitrile, isobutyronitrile, n- butyronitrile, methoxyacetonitrile, 2-methylbutyronitrile, isovaleronitrile, n-valeronitrile, n-capronitrile, 3-methoxypropionitrile, 3-ethoxypropionitrile, 3,3'-oxydipropionitrile, n-heptanenitrile, glycolonitrile, benzonitrile, ethylene cyanohydrin, succinonitrile, acetone cyanohydrin, 3-n-butoxypropionitrile, and the like, as well as combinations of any two or more thereof.
- Exemplary sulfoxide co-solvents contemplated for use in the new composition include, but are not limited to, dimethyl sulfoxide (DMSO), di- n-butyl sulfoxide, tetramethylene sulfoxide, methyl phenyl sulfoxide, and the like, as well as combinations of any two or more thereof.
- DMSO dimethyl sulfoxide
- di- n-butyl sulfoxide di- n-butyl sulfoxide
- tetramethylene sulfoxide methyl phenyl sulfoxide
- methyl phenyl sulfoxide and the like, as well as combinations of any two or more thereof.
- Exemplary amide co-solvents contemplated for use in the new composition include, but are not limited to, dimethyl formamide (DMF), dimethyl acetamide, acylamide, 2-acetamidoethanol, N.N-dimethyl-m- toluamide, trifluoroacetamide, N,N-dimethylacetamide, N,N- diethyldodecanamide, ⁇ -caprolactam, N,N-diethylacetamide, N-tert- butylformamide, formamide, pivalamide, N-butyramide, N,N- dimethylacetoacetamide, N-methyl formamide, N,N-diethylformamide, N-formylethylamine, acetamide, N,N-diisopropyIformamide, 1- formylpiperidine, N-methylformanilide, and the like, as well as combinations of any two or more thereof.
- DMF dimethyl formamide
- acetamide dimethyl acet
- Exemplary amine co-solvents contemplated for use in the new composition include, but are not limited to, mono-, di-, and tri-alkyl amines, cyclic amines (such as, e.g., pyrrolidine), aromatic amines (such as, e.g., pyridine) and the like, as well as combinations of any two or more thereof.
- the amine co-solvent is pyridine.
- Exemplary carboxylic acid co-solvents contemplated for use in the new composition include, but are not limited to, C-- up to about C Q straight or branched chain carboxylic acids, as well as combinations of any two or more thereof.
- the carboxylic acid co-solvent is formic acid.
- the co-solvent is selected from an alcohol, an alcohol ether, and combinations thereof. In one embodiment, the co- solvent is selected from normal propyl alcohol, 1-methoxy-2-propanol, and combinations thereof.
- the co-solvent is present in an amount from about 5% by weight to about 60% by weight, based on the total weight of liquid. In one embodiment, the co-solvent is present in an amount of from about 10% by weight to about 30% by weight.
- the metal cations contemplated for use in the new composition are present in the form of water soluble salts.
- Suitable anions include, but are not limited to, halide, carbonate, bicarbonate, sulfate, nitrate, acetate, tetrafluoroborate, and hexafluorophosphate.
- Combinations of salts can be used.
- Metal hydroxides can be used, however the resulting increase in pH may adversely affect the properties of the conductive polymer at higher concentrations.
- aqueous poly(ethylenedioxythiophene) (“PEDT") dispersions for OLED applications, Baytron ® -P VP Al 4083 and CH8000, from H. C.
- a pH below 2 With Baytron-P®, adjusting the pH to higher levels can have a deleterious effect on the electrical properties of the conductive polymer and their functional effectiveness as a buffer layer in OLEDs.
- a pH well above 2 must be avoided when the metal cation is added as an aqueous basic solution, such as aqueous sodium hydroxide solution.
- the metal cation is selected from Na + , K + , Cs + Mg +2 , and combinations thereof. In one embodiment, at least a portion of the metal cation is present as a salt with an anion selected from chloride, hydroxide, and carbonate.
- the metal cation is present in a concentration greater than about 0.4 mmol per gram of doped conductive polymer. In one embodiment, the metal cation is present in a concentration between about 0.5 and 3 mmol per gram of doped conductive polymer. In one embodiment, the metal cation is present in a concentration between about 0.6 and 2 mmol per gram of doped conductive polymer.
- the new composition can be formed into a layer.
- layer is used interchangeably with the term “film” and refers to a coating covering a desired area.
- the area can be as large as an entire device or as small as a specific functional area such as the actual visual display, or as small as a single sub-pixel.
- Films can be formed by any conventional deposition technique. Typical liquid deposition techniques include, but are not limited to, continuous deposition techniques such as spin coating, gravure coating, curtain coating, dip coating, slot-die coating, spray coating, and continuous nozzle coating; and discontinuous deposition techniques such as ink jet printing, gravure printing, and screen printing. Layers may also be formed by thermal transfer. A donor sheet of the desired material is exposed to a thermal head or laser to transfer the material from the donor onto a desired substrate.
- the new compositions can be used to form buffer layers in an electronic device.
- buffer layer as used herein, is intended to mean an electrically conductive or semiconductive layer which can be used between an anode and an active organic material.
- a buffer layer is believed to accomplish one or more functions in an organic electronic device, including, but not limited to planarization of the underlying layer, hole transport, hole injection, scavenging of impurities, such as oxygen and metal ions, among other aspects to facilitate or to improve the performance of an organic electronic device.
- the organic electronic device comprises an electroactive layer positioned between two electrical contact layers, wherein the device includes a layer made from the new composition.
- One embodiment is illustrated in one type of OLED device, as shown in FIG.
- the device may include a support or substrate (not shown) that can be adjacent to the anode layer 110 or the cathode layer 150. Most frequently, the support is adjacent the anode layer 110.
- the support can be flexible or rigid, organic or inorganic. Generally, glass or flexible organic films are used as a support.
- the anode layer 110 is an electrode that is more efficient for injecting holes compared to the cathode layer 150.
- the anode can include materials containing a metal, mixed metal, alloy, metal oxide or mixed oxide. Suitable materials include the mixed oxides of the Group 2 elements (i.e., Be, Mg, Ca, Sr, Ba, Ra), the Group 11 elements, the elements in Groups 4, 5, and 6, and the, Group 8-10 transition elements. If the anode layer 110 is to be light transmitting, mixed oxides of Groups 12, 13 and 14 elements, such as indium-tin-oxide, may be used. As used herein, the phrase "mixed oxide” refers to oxides having two or more different cations selected from the Group 2 elements or the Groups 12, 13, or 14 elements.
- anode layer 110 examples include, but are not limited to, indium-tin-oxide ("ITO"), aluminum-tin-oxide, gold, silver, copper, and nickel.
- ITO indium-tin-oxide
- the anode may also comprise an organic material such as polyaniline, polythiophene, or polypyrrole.
- the anode layer 110 may be formed by a chemical or physical vapor deposition process or spin-coating process.
- Chemical vapor deposition may be performed as a plasma-enhanced chemical vapor deposition ("PECVD") or metal organic chemical vapor deposition ("MOCVD”).
- Physical vapor deposition can include all forms of sputtering, including ion beam sputtering, as well as e-beam evaporation and resistance evaporation.
- Specific forms of physical vapor deposition include rf magnetron sputtering and inductively-coupled plasma physical vapor deposition ("IMP-PVD"). These deposition techniques are well known within the semiconductor fabrication arts.
- the anode layer 110 may be patterned during a lithographic operation.
- the pattern may vary as desired.
- the layers can be formed in a pattern by, for example, positioning a patterned mask or resist on the support prior to applying the first electrical contact layer material.
- the layers can be applied as an overall layer (also called blanket deposit) and subsequently patterned using, for example, a patterned resist layer and wet chemical or dry etching techniques. Other processes for patterning that are well known in the art can also be used.
- the anode layer 110 typically is formed into substantially parallel strips having lengths that extend in substantially the same direction.
- Buffer layer 120 can be formed using any deposition technique well-known to those skilled in the art, as discussed above.
- the electroluminescent (“EL”) layer 130 may typically be any organic EL material, including, but not limited to, fluorescent dyes, fluorescent and phosphorescent metal complexes, conjugated polymers, and mixtures thereof.
- fluorescent dyes include, but are not limited to, pyrene, perylene, rubrene, derivatives thereof, and mixtures thereof.
- metal complexes include, but are not limited to, metal chelated oxinoid compounds, such as tris(8- hydroxyquinolato)aluminum (Alq3); cyclometalated iridium and platinum electroluminescent compounds, such as complexes of Iridium with phenylpyridine, phenylquinoline, or phenylpyrimidine ligands as disclosed in Petrov et al., Published PCT Application WO 02/02714, and organometallic complexes described in, for example, published applications US 2001/0019782, EP 1191612, WO 02/15645, and EP 1191614; and mixtures thereof.
- metal chelated oxinoid compounds such as tris(8- hydroxyquinolato)aluminum (Alq3)
- cyclometalated iridium and platinum electroluminescent compounds such as complexes of Iridium with phenylpyridine, phenylquinoline, or phenylpyrimidine ligands
- Electroluminescent emissive layers comprising a charge carrying host material and a metal complex have been described by Thompson et al., in U.S. Patent 6,303,238, and by Burrows and Thompson in published PCT applications WO 00/70655 and WO 01/41512.
- conjugated polymers include, but are not limited to poly(phenylenevinylenes), polyfluorenes, poly(spirobifluorenes), polythiophenes, poly(p-phenylenes), copolymers thereof, and mixtures thereof.
- Electroluminescent polymers have been disclosed in, for example, published PCT applications WO 97/33323 and WO 98/27136, and in published German application DE 19615128. Combinations of emissive materials can be used.
- the particular material chosen may depend on the specific application, potentials used during operation, or other factors.
- the EL layer 130 containing the electroluminescent organic material can be applied using any number of techniques including vapor deposition, solution processing techniques or thermal transfer.
- an EL polymer precursor can be applied and then converted to the polymer, typically by heat or other source of external energy (e.g., visible light or UV radiation).
- Optional layer 140 can function both to facilitate electron injection/transport, and can also serve as a confinement layer to prevent quenching reactions at layer interfaces. More specifically, layer 140 may promote electron mobility and reduce the likelihood of a quenching reaction if layers 130 and 150 would otherwise be in direct contact.
- Examples of materials for optional layer 140 include, but are not limited to, metal-chelated oxinoid compounds (e.g., Alq3 or the like); phenanthroline- based compounds (e.g., 2,9-dimethyl-4,7-diphenyl-1 ,10-phenanthroline ("DDPA"), 4,7-diphenyl-1 ,10-phenanthroline (“DPA”), or the like); azole compounds (e.g., 2-(4-biphenylyl)-5-(4-t-butylphenyl)-1 ,3,4-oxadiazole (“PBD” or the like), 3-(4-biphenylyl)-4-phenyl-5-(4-t-butylphenyl)-1 ,2,4- triazole (“TAZ” or the like); other similar compounds; or any one or more combinations thereof.
- metal-chelated oxinoid compounds e.g., Alq3 or the like
- phenanthroline- based compounds e
- optional layer 140 may be inorganic and comprise BaO, LiF, Li2 ⁇ , or the like.
- the cathode layer 150 is an electrode that is particularly efficient for injecting electrons or negative charge carriers.
- the cathode layer 150 can be any metal or nonmetal having a lower work function than the first electrical contact layer (in this case, the anode layer 110).
- the term "lower work function” is intended to mean a material having a work function no greater than about 4.4 eV.
- “higher work function” is intended to mean a material having a work function of at least approximately 4.4 eV.
- Materials for the cathode layer can be selected from alkali metals of Group 1 (e.g., Li, Na, K, Rb, Cs,), the Group 2 metals (e.g., Mg, Ca, Ba, or the like), the Group 12 metals, the lanthanides (e.g., Ce, Sm, Eu, or the like), and the actinides (e.g., Th, U, or the like). Materials such as aluminum, indium, yttrium, and combinations thereof, may also be used. Specific non-limiting examples of materials for the cathode layer 150 include, but are not limited to, barium, lithium, cerium, cesium, europium, rubidium, yttrium, magnesium, samarium, and alloys and combinations thereof.
- the cathode layer 150 is usually formed by a chemical or physical vapor deposition process. In general, the cathode layer will be patterned, as discussed above in reference to the anode layer 110. If the device lies within an array, the cathode layer 150 may be patterned into substantially parallel strips, where the lengths of the cathode layer strips extend in substantially the same direction and substantially perpendicular to the lengths of the anode layer strips. Electronic elements called pixels are formed at the cross points (where an anode layer strip intersects a cathode layer strip when the array is seen from a plan or top view).
- additional layer(s) may be present within organic electronic devices.
- a layer (not shown) between the buffer layer 120 and the EL layer 130 may facilitate positive charge transport, band-gap matching of the layers, function as a protective layer, or the like.
- additional layers (not shown) between the EL layer 130 and the cathode layer 150 may facilitate negative charge transport, band-gap matching between the layers, function as a protective layer, or the like. Layers that are known in the art can be used. In addition, any of the above-described layers can be made of two or more layers.
- inorganic anode layer 110, the buffer layer 120, the EL layer 130, and cathode layer 150 may be surface treated to increase charge carrier transport efficiency.
- the choice of materials for each of the component layers may be determined by balancing the goals of providing a device with high device efficiency with the cost of manufacturing, manufacturing complexities, or potentially other factors.
- inorganic anode layer 110 is usually no greater than approximately 500 nm, for example, approximately 10-200 nm; buffer layer 120, is usually no greater than approximately 250 nm. In one embodiment, the second layer is less than 10nm.
- EL layer 130 is usually no greater than approximately 100 nm, for example, approximately 50-80 nm; optional layer 140 is usually no greater than approximately 100 nm, for example, approximately 20-80 nm; and cathode layer 150 is usually no greater than approximately 100 nm, for example, approximately 1-50 nm. If the anode layer 110 or the cathode layer 150 needs to transmit at least some light, the thickness of such layer may not exceed approximately 100 nm.
- OLEDs organic light emitting diodes
- electrons and holes injected from the cathode 150 and anode 110 layers, respectively, into the EL layer 130, form negative and positively charged polar ions in the polymer.
- These polar ions migrate under the influence of the applied electric field, forming a polar ion exciton with an oppositely charged species and subsequently undergoing radiative recombination.
- a sufficient potential difference between the anode and cathode usually less than approximately 12 volts, and in many instances no greater than approximately 5 volts, may be applied to the device. The actual potential difference may depend on the use of the device in a larger electronic component.
- the anode layer 110 is biased to a positive voltage and the cathode layer 150 is at substantially ground potential or zero volts during the operation of the electronic device.
- a battery or other power source(s) may be electrically connected to the electronic device as part of a circuit but is not illustrated in FIG. 1. It has been found in some OLED devices having an anode patterned into parallel strips, that a defect known as "wide column gap” (“WCG”) can occur. In this context, the anode strips are running in the verticl (“column”) direction on the display as normally viewed. The WCG defect occurs anywhere on the display where two adjacent anode lines are biased at "on” and "off” voltages.
- the defect manifests itself as an apparent growth of the dark region between the adjacent anode lines, distorting the image.
- the WCG defect is, to some extent, reversible and the degraded area recovers when the anodes are returned to a common voltage. Recovery of the area degraded by the WCG defect can sometimes be accelerated by inverting the image so the "on" and “off voltages are reversed.
- the term "organic electronic device” is intended to mean a device including one or more semiconductor layers or materials.
- Organic electronic devices include: (1) devices that convert electrical energy into radiation (e.g., a light-emitting diode, light-emitting diode display, or diode laser), (2) devices that detect signals through electronics processes (e.g., photodetectors (e.g., photoconductive cells, photoresistors, photoswitches, phototransistors, phototubes), IR detectors), (3) devices that convert radiation into electrical energy (e.g., a photovoltaic device or solar cell), and (4) devices that include one or more electronic components that include one or more organic semi-conductor layers (e.g., a transistor or diode).
- devices that convert electrical energy into radiation e.g., a light-emitting diode, light-emitting diode display, or diode laser
- devices that detect signals through electronics processes e.g., photodetectors (e.g., photoconductive cells, photoresistors, photoswitches, phototransistors, phototubes), IR detectors)
- buffer layers made from the new compositions are effective at preventing WCG in OLED displays.
- Glass/ITO substrates having an ITO thickness of about 100 to 150 nm were used.
- the ITO was patterned into parallel lines about 370 ⁇ m wide which were spaced about 50 ⁇ m apart.
- the ITO line plates were then spin-coated with a photo-resist and subsequently patterned into mushroom-shaped lines perpendicular to the ITO lines. Adjacent mushroom lines were spaced 370 ⁇ m apart, therefore forming pixels having the dimension of 370 ⁇ mx370 ⁇ m.
- the substrates with patterned ITO and mushroom lines were cleaned and subsequently treated with UV ozone.
- the buffer layer was spin-coated onto the ITO/mushroom/glass substrates to a thickness of about 200 nm.
- the spin-coated films were then baked at 90 °C in vacuum for 30 minutes.
- a 1 % (w/v) toluene solution of a polyphenylene vinylene polymer (Super Yellow from Covion, Frankfurt, Germany) was spin-coated on top of the dried buffer layer and subsequently baked at 130 °C in nitrogen for 30 minutes, with a final thickness of about 70 nm.
- a 3.0 nm thick barium layer and 350 nm thick aluminum layer were deposited on the emitter layer to serve as a cathode.
- the mushroom lines were there to prevent cathodes from joining together.
- a glass cover was placed over the device to protect it from oxygen and moisture.
- a forward bias of 3.5 volts was applied across all the device cathodes and anodes, and a photograph was taken. This was the "base photograph”.
- the forward bias across the device was then turned off and +14 Volts DC (Direct Current) electrical bias was applied to the first anode column visible in the base photograph, while the second anode column, adjacent to the first anode column and also visible in the base photograph, was connected to the electrical ground.
- the remainder of the cathodes and anodes were left electrically floating.
- the electrical bias between the two anode columns was kept on for 64 hours and the electrical current between the 2 columns was recorded at the start and at the finish of applying the bias.
- Comparative Example 1 In this Comparative Example, Baytron-P® CH8000 as received, was used as the buffer layer.
- the CH8000 dispersion has a pH of about 1.6 and contains 0.4 mmoles sodium ion per gram of dried polymer. It has a sulfate content less than 10 ppm.
- Devices were fabricated and tested as described above. The effect of applying reverse bias is shown in Table 1. It can be seen that a device having a buffer layer made from as-received Baytron-P® CH8000 with a sodium level of 0.4 mmoles per gram of dried polymer shows a serious wide column defect problem.
- Lewatit S100 a trade name from Bayer, Pittsburgh, PA, for sodium sulfonate of crosslinked polystyrene
- Lewatit® MP62 WS a trade from Bayer, Pittsburgh, PA
- Lumination Green from Dow Chemicals (Midland, Michigan) was spin- coated on top of the buffer layer films and subsequently baked at 100°C in vacuum for 30 minutes. The final thickness was 740 A .
- a 3nm thick barium layer and a 300-500nm aluminum layer were deposited on the Lumination Green films to serve as a cathode.
- the device data summarized in Table 2 clearly shows that Baytron-P ® AI4083 has a much higher voltage and much lower efficiency when the pH is increased from 1.8 to 4 or 7. This result clearly shows that Baytron-P ® starts to lose effectiveness as a buffer layer when adjusted to a pH greater than ⁇ 2.
- This example illustrates the effect of voltage, operating time, and deionization of the hole injection material on WCG defect formation.
- Devices were fabricated and tested as described in the test procedure above.
- the buffer layer was either as-received Baytron-P® CH8000, or deionized Baytron-P® CH8000.
- the defect was not sensitive to the applied voltage or the duration of operation. However, the defect seemed sensitive to ion concentration in the buffer layer, as indicated by the fact that the defect was more severe when deionized PEDOT dispersion was used, where sodium was mostly removed.
- Example 1 This example illustrates the effect of additive concentration and metal cation type on the WCG defect. Devices were fabricated and tested as described in the above Test Method. The buffer layers were made from Baytron-P® CH8000 with different amounts of added cations, as indicated in Table 4 below.
- This example illustrates the effect of co-solvents and metal cation concentration on the WCG defect.
- Example 1 A generally higher voltage was applied to these samples than in Example 1 to increase the general severity of the defect. Hence, the ratings in this table can not be compared with the ratings in other tables tested at a different voltage.
- the coating homogeneity and film quality were significantly better for the samples containing co-solvent.
- NaCI may be a more effective additive than NaOH or Na 2 C0 3 , at least with the exact parameters used for the samples in this Example. While 0.8 mmol/g of Na + from NaOH or Na 2 C0 3 lowered the severity ranking to 1, the same concentration of Na + that was achieved from NaCI completely eliminated the defect.
- Example 3 This example tests the limit of the operating conditions that can be handled by salt and co-solvent(s) in terms of WCG resistance. Devices were fabricated and tested as in the Test Method, above.
- Example 4 This example illustrates the effect of metal cation additives and co- solvents on recovery. Devices were fabricated and tested as in the Test Method, above.
- the buffer layer was PEDOT with the additive concentrations shown in Table 7.
- Table 7 The buffer layer was PEDOT with the additive concentrations shown in Table 7.
- the compositions shown in Table 7 were made into display devices and driven with a Soloman 1301 driver.
- the adjacent anode columns were held at a voltage difference of about 12.3 V, and the row (cathode) voltages were scanned at a rate of 80 Hz.
- the "on" voltages were adjusted to achieve a brightness level of about 200 cd/m 2 . (This did not affect the voltage difference across the anode column lines).
- the displays were tested in this mode for 82 hours and the severity of the defect was noted as shown below.
- the display devices were tested for an additional period of time for a total of 101 hours of operation. No further increase in the severity of the WCG defect occurred between the 82-hour point and the 101 -hour point.
- the displays were turned off and allowed to recover for about 16 hours. Then, they were lit briefly to be inspected for the extent of recovery.
- the first sample which included no additional metal additives and no co-solvents, showed almost no recovery in the 16- hour period.
- Example 3 suggests that there is a limit to the harshness of operating condition at which salts and co-solvents can prevent WCG defect formation. Thus, if the operating condition will be above that limit, it may be preferable to use Na 2 C0 3 and NaOH as dopant sources because they showed better recovery in Example 4.
Abstract
Description
Claims
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