KR101559590B1 - 전도성 중합체의 술폰화 및 oled 소자, 광기전력 소자 및 esd 소자 - Google Patents
전도성 중합체의 술폰화 및 oled 소자, 광기전력 소자 및 esd 소자 Download PDFInfo
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- KR101559590B1 KR101559590B1 KR1020097003476A KR20097003476A KR101559590B1 KR 101559590 B1 KR101559590 B1 KR 101559590B1 KR 1020097003476 A KR1020097003476 A KR 1020097003476A KR 20097003476 A KR20097003476 A KR 20097003476A KR 101559590 B1 KR101559590 B1 KR 101559590B1
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- 238000006277 sulfonation reaction Methods 0.000 title claims description 52
- 229920001940 conductive polymer Polymers 0.000 title abstract description 35
- 229920000123 polythiophene Polymers 0.000 claims abstract description 223
- 239000000203 mixture Substances 0.000 claims abstract description 83
- 238000002347 injection Methods 0.000 claims abstract description 24
- 239000007924 injection Substances 0.000 claims abstract description 24
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims abstract description 22
- 230000005525 hole transport Effects 0.000 claims abstract description 13
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229920000642 polymer Polymers 0.000 claims description 159
- 238000000034 method Methods 0.000 claims description 67
- -1 3-substituted thiophene Chemical class 0.000 claims description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 55
- 238000000576 coating method Methods 0.000 claims description 47
- 229910052717 sulfur Inorganic materials 0.000 claims description 38
- 239000011248 coating agent Substances 0.000 claims description 37
- 239000011593 sulfur Substances 0.000 claims description 36
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 34
- 229920001059 synthetic polymer Polymers 0.000 claims description 29
- 239000007787 solid Substances 0.000 claims description 26
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 23
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 21
- 239000003153 chemical reaction reagent Substances 0.000 claims description 19
- 239000008199 coating composition Substances 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 229920001577 copolymer Polymers 0.000 claims description 15
- 229920001400 block copolymer Polymers 0.000 claims description 13
- 239000006184 cosolvent Substances 0.000 claims description 12
- 125000000524 functional group Chemical group 0.000 claims description 12
- 229930192474 thiophene Natural products 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 10
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 10
- 229920001519 homopolymer Polymers 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 229920003169 water-soluble polymer Polymers 0.000 claims description 7
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
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- 239000003990 capacitor Substances 0.000 claims description 5
- 125000002091 cationic group Chemical group 0.000 claims description 5
- 230000003068 static effect Effects 0.000 claims description 5
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 3
- 229920005603 alternating copolymer Polymers 0.000 claims description 3
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 3
- 239000003607 modifier Substances 0.000 claims description 3
- 150000003577 thiophenes Chemical class 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract description 99
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 88
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 125000003118 aryl group Chemical group 0.000 description 20
- 238000004519 manufacturing process Methods 0.000 description 20
- 239000011521 glass Substances 0.000 description 18
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 239000006185 dispersion Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 13
- 239000002322 conducting polymer Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
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- 125000003107 substituted aryl group Chemical group 0.000 description 11
- 125000001072 heteroaryl group Chemical group 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
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- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 229920001665 Poly-4-vinylphenol Polymers 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 8
- 125000000732 arylene group Chemical group 0.000 description 8
- 125000004104 aryloxy group Chemical group 0.000 description 8
- 229920000547 conjugated polymer Polymers 0.000 description 8
- 238000000151 deposition Methods 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 239000011159 matrix material Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 7
- 229920002223 polystyrene Polymers 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 230000006870 function Effects 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 238000013086 organic photovoltaic Methods 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 125000005415 substituted alkoxy group Chemical group 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
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- 150000003384 small molecules Chemical class 0.000 description 5
- 125000000547 substituted alkyl group Chemical group 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 4
- JNGDCMHTNXRQQD-UHFFFAOYSA-N 3,6-dioxocyclohexa-1,4-diene-1,2,4,5-tetracarbonitrile Chemical compound O=C1C(C#N)=C(C#N)C(=O)C(C#N)=C1C#N JNGDCMHTNXRQQD-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- ZBIKORITPGTTGI-UHFFFAOYSA-N [acetyloxy(phenyl)-$l^{3}-iodanyl] acetate Chemical compound CC(=O)OI(OC(C)=O)C1=CC=CC=C1 ZBIKORITPGTTGI-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 4
- 229940092714 benzenesulfonic acid Drugs 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
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- JYJVVHFRSFVEJM-UHFFFAOYSA-N iodosobenzene Chemical compound O=IC1=CC=CC=C1 JYJVVHFRSFVEJM-UHFFFAOYSA-N 0.000 description 4
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- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
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Abstract
Description
Claims (98)
- (i) 하나 이상의 알콕시 또는 알킬 치환체, 및(ii) 폴리티오펜 골격에 직접 결합하는 술포네이트 황을 포함하는 하나 이상의 술포네이트 치환체를 포함하고, 술폰화를 제외하고 70% 이상의 위치규칙성 정도를 가지며, 상기 위치규칙성이 HT (머리-꼬리), HH-TT 또는 TT-HT 커플링된 폴리(3-치환된 티오펜)인 수용성 또는 수분산성 위치규칙적 폴리티오펜을 포함하는 조성물.
- 제1항에 있어서, 술포네이트 치환체가 염 형태인 조성물.
- 제2항에 있어서, 상기 염 형태가 이미다졸리늄, 티아졸리늄, 또는 옥사졸리늄을 포함하는 것인 조성물.
- 제1항에 있어서, 폴리티오펜이 위치규칙적 HT 커플링된 폴리(3-치환된 티오펜)인 조성물.
- 제1항에 있어서, 폴리티오펜이 수용성이고 도핑된 것인 조성물.
- 제1항에 있어서, 폴리티오펜이 교대 공중합체, 바이티오펜 단량체로부터 제조된 중합체, 티오펜의 단일중합체, 티오펜 단위를 포함하는 공중합체, 또는 하나 이상의 폴리티오펜 블록을 포함하는 블록 공중합체인 조성물.
- 제1항에 있어서, 수용성 또는 수분산성 위치규칙적 폴리티오펜이 가교된 형태인 조성물.
- 제1항에 있어서, 폴리티오펜이 250 ㎎ 이하 KOH/g 중합체의 산가를 갖는 것을 특징으로 하는 조성물.
- 제1항에 있어서, 폴리티오펜이 25% 내지 75%의 술폰화 정도를 갖는 것을 특징으로 하는 조성물.
- 제1항에 있어서, 폴리티오펜이 수용성 및 단일중합체이고 50 내지 250 ㎎ KOH/g 중합체의 산가를 갖는 것인 조성물.
- 제1항에 있어서, 폴리티오펜이 수용성이고 염 형태인 조성물.
- 제11항에 있어서, 상기 염 형태가 이미다졸리늄, 티아졸리늄, 또는 옥사졸리늄을 포함하는 것인 조성물.
- 제1항에 있어서, 폴리티오펜이 수용성이고, 도핑되고, 90% 이상의 위치규칙성 정도를 갖는 위치규칙적 폴리티오펜이고, 산 형태인 것인 조성물.
- 제1항에 있어서, 알콕시 치환체가 메톡시에톡시에톡시 단위를 포함하는 것인 조성물.
- 하나 이상의 알콕시 또는 알킬 치환체를 포함하고, 술폰화를 제외하고 70% 이상의 위치규칙성 정도를 가지며 상기 위치규칙성이 HT, HH-TT 또는 TT-HT 커플링된 폴리(3-치환된 티오펜)인 가용성 위치규칙적 폴리티오펜을 술폰화 시약과 반응시켜서 이 폴리티오펜이 폴리티오펜 골격에 직접 결합하는 술포네이트 황을 포함하는 하나 이상의 술포네이트 치환체를 포함하도록 하는 것을 포함하는, 제1항에 따른 조성물의 제조 방법.
- 제15항에 있어서, 술폰화 시약이 황산 또는 술페이트 화합물인 제조 방법.
- 제15항에 있어서, 반응한 폴리티오펜이 도핑된 것인 제조 방법.
- 제15항에 있어서, 반응이 10% 이상의 술폰화 정도를 제공하는 것인 제조 방법.
- 제15항에 있어서, 술폰화 시약이 황산이고, 반응이 75% 이상의 술폰화 정도를 제공하고, 폴리티오펜이 90% 이상의 위치규칙성 정도를 갖는 위치규칙적 폴리티오펜인 제조 방법.
- 제15항에 있어서, 반응이 50% 이상의 술폰화 정도를 제공하고, 폴리티오펜이 98% 이상의 위치규칙성 정도를 갖는 위치규칙적 폴리티오펜인 제조 방법.
- (A) 물,(B) (i) 하나 이상의 알콕시 또는 알킬 치환체, 및(ii) 폴리티오펜 골격에 직접 결합하는 술포네이트 황을 포함하는 하나 이상의 술포네이트 치환체를 포함하고, 술폰화를 제외하고 70% 이상의 위치규칙성 정도를 가지며, 상기 위치규칙성이 HT, HH-TT 또는 TT-HT 커플링된 폴리(3-치환된 티오펜)인 수용성 또는 수분산성 위치규칙적 폴리티오펜, 및(C) 상기 (B)와 상이한 합성 중합체를 포함하는 코팅 조성물.
- 제21항에 있어서, 유기 공용매를 더 포함하고, 물의 중량이 유기 공용매의 중량보다 더 많은 것인 코팅 조성물.
- 제21항에 있어서, (B) 및 (C)와 상이한 제 2 합성 중합체를 더 포함하는 코팅 조성물.
- 제21항에 있어서, 합성 중합체가 수용성 중합체이고, 측쇄기에 극성 관능기를 갖는 탄소 골격을 갖는 것인 코팅 조성물.
- 제21항에 있어서, 합성 중합체 (C)의 중량이 위치규칙적 폴리티오펜 (B)의 양의 3 배 이상이거나, 위치규칙적 폴리티오펜 중합체 (B)의 양이 (B) 및 (C)의 총량 기준으로 5 중량% 내지 25 중량%인 코팅 조성물.
- (A) 물을 제공하고,(B) (i) 하나 이상의 알콕시 또는 알킬 치환체, 및(ii) 폴리티오펜 골격에 직접 결합하는 황을 포함하는 하나 이상의 술포네이트 치환체를 포함하고, 술폰화를 제외하고 70% 이상의 위치규칙성 정도를 가지며, 상기 위치규칙성이 HT, HH-TT 또는 TT-HT 커플링된 폴리(3-치환된 티오펜)인 수용성 또는 수분산성 위치규칙적 폴리티오펜을 제공하고,(C) 상기 (B)와 상이한 합성 중합체를 제공하고,(D) 상기 (A), (B) 및 (C)를 어떠한 순서로든 합쳐서 코팅 조성물을 형성하는 것을 포함하는, 코팅 조성물의 제조 방법.
- 고체 표면; 및이 표면 위에 배치된 코팅물을 포함하며, 상기 코팅물은(i) 하나 이상의 알콕시 또는 알킬 치환체 및(ii) 폴리티오펜 골격에 직접 결합하는 술포네이트 황을 포함하는 하나 이상의 술포네이트 치환체를 포함하고, 술폰화를 제외하고 70% 이상의 위치규칙성 정도를 가지며, 상기 위치규칙성이 HT, HH-TT 또는 TT-HT 커플링된 폴리(3-치환된 티오펜)인 수용성, 수분산성 또는 수팽창성 위치규칙적 폴리티오펜을 포함하는 조성물을 포함하는 것인 코팅된 기판.
- (B) (i) 하나 이상의 알콕시 또는 알킬 치환체, 및(ii) 폴리티오펜 골격에 직접 결합하는 술포네이트 황을 포함하는 하나 이상의 술포네이트 치환체를 포함하고, 술폰화를 제외하고 70% 이상의 위치규칙성 정도를 가지며, 상기 위치규칙성이 HT, HH-TT 또는 TT-HT 커플링된 폴리(3-치환된 티오펜)인 수용성, 수분산성 또는 수팽창성 위치규칙적 폴리티오펜, 및(C) 상기 (B)와 상이한 합성 중합체를 포함하는 코팅된 기판.
- 제1항에 따른 조성물을 포함하는 층을 포함하는 소자.
- 제29항에 있어서, 층이 정공 주입층 또는 정공 수송층인 소자.
- 제29항에 있어서, OLED 소자, PLED 소자, SMOLED 소자, 광기전력 소자, 센서, 초고용량 커패시터, 양이온 변환기, 약물 방출 소자, 전기변색 소자, 트랜지스터, 전계 효과 트랜지스터, 전극 개질제, 유기 전계 효과 트랜지스터를 위한 전극 개질제, 작동기, 투명 전극, 또는 정전기 소산 소자로부터 선택된 소자.
- 제29항에 있어서, 소자가 둘 이상의 전극 및 하나 이상의 발광 또는 광활성 층을 포함하고, 조성물이 전극 위의 코팅물인 소자.
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CN101563388B (zh) | 2013-05-15 |
EP2049582B1 (en) | 2019-02-27 |
WO2008073149A9 (en) | 2009-04-02 |
US8946378B2 (en) | 2015-02-03 |
EP2537874A1 (en) | 2012-12-26 |
EP2537874B1 (en) | 2021-05-19 |
CA2658181C (en) | 2015-01-06 |
US20120037852A1 (en) | 2012-02-16 |
US8017241B2 (en) | 2011-09-13 |
WO2008073149A3 (en) | 2008-11-06 |
JP2010505005A (ja) | 2010-02-18 |
US8399604B2 (en) | 2013-03-19 |
TW200829647A (en) | 2008-07-16 |
JP5284956B2 (ja) | 2013-09-11 |
IL196622A (en) | 2013-02-28 |
WO2008073149A2 (en) | 2008-06-19 |
MY148477A (en) | 2013-04-30 |
US20140054509A1 (en) | 2014-02-27 |
KR20090042800A (ko) | 2009-04-30 |
TWI470024B (zh) | 2015-01-21 |
CN101563388A (zh) | 2009-10-21 |
EP2049582A2 (en) | 2009-04-22 |
KR20140067164A (ko) | 2014-06-03 |
CA2658181A1 (en) | 2008-06-19 |
WO2008073149A8 (en) | 2009-02-26 |
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