TWI614317B - 電荷輸送性清漆 - Google Patents
電荷輸送性清漆 Download PDFInfo
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- TWI614317B TWI614317B TW103109923A TW103109923A TWI614317B TW I614317 B TWI614317 B TW I614317B TW 103109923 A TW103109923 A TW 103109923A TW 103109923 A TW103109923 A TW 103109923A TW I614317 B TWI614317 B TW I614317B
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- 239000002966 varnish Substances 0.000 title claims abstract description 67
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 56
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 48
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 42
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 29
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 29
- 239000000126 substance Substances 0.000 claims abstract description 28
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 239000002019 doping agent Substances 0.000 claims abstract description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 17
- 125000002843 carboxylic acid group Chemical group 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- 125000000542 sulfonic acid group Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 100
- -1 diphenylamino group Chemical group 0.000 claims description 65
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 34
- 239000000758 substrate Substances 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 238000002347 injection Methods 0.000 claims description 12
- 239000007924 injection Substances 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000003172 aldehyde group Chemical group 0.000 claims description 7
- 238000010304 firing Methods 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 238000005401 electroluminescence Methods 0.000 claims description 4
- 230000005525 hole transport Effects 0.000 claims description 3
- 230000005611 electricity Effects 0.000 claims 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 abstract description 4
- ZNPKAOCQMDJBIK-UHFFFAOYSA-N nitrocyanamide Chemical compound [O-][N+](=O)NC#N ZNPKAOCQMDJBIK-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- ZXYFGZNMDRNOGQ-UHFFFAOYSA-N ac1lawgt Chemical group [S]O ZXYFGZNMDRNOGQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 239000010408 film Substances 0.000 description 43
- 239000010410 layer Substances 0.000 description 33
- 239000002904 solvent Substances 0.000 description 26
- 239000002253 acid Substances 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
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- 239000010409 thin film Substances 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 11
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- FDRNXKXKFNHNCA-UHFFFAOYSA-N 4-(4-anilinophenyl)-n-phenylaniline Chemical compound C=1C=C(C=2C=CC(NC=3C=CC=CC=3)=CC=2)C=CC=1NC1=CC=CC=C1 FDRNXKXKFNHNCA-UHFFFAOYSA-N 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
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- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 5
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 150000001448 anilines Chemical class 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 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
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical class O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- 241000208340 Araliaceae Species 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 4
- 235000003140 Panax quinquefolius Nutrition 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 235000008434 ginseng Nutrition 0.000 description 4
- 239000002861 polymer material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical group C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 3
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 0 Cc(c(*)c1*)c([C@](*)O)c(*)c1-c(c(**)c(**)c(C)c1**)c1O* Chemical compound Cc(c(*)c1*)c([C@](*)O)c(*)c1-c(c(**)c(**)c(C)c1**)c1O* 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 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 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 3
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 239000001211 (E)-4-phenylbut-3-en-2-one Substances 0.000 description 2
- DCTMXCOHGKSXIZ-UHFFFAOYSA-N (R)-1,3-Octanediol Chemical compound CCCCCC(O)CCO DCTMXCOHGKSXIZ-UHFFFAOYSA-N 0.000 description 2
- ONUFSRWQCKNVSL-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(2,3,4,5,6-pentafluorophenyl)benzene Chemical group FC1=C(F)C(F)=C(F)C(F)=C1C1=C(F)C(F)=C(F)C(F)=C1F ONUFSRWQCKNVSL-UHFFFAOYSA-N 0.000 description 2
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- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- PKURFTDCIWJBDF-UHFFFAOYSA-N 2-hexylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CCCCCC)=CC=C21 PKURFTDCIWJBDF-UHFFFAOYSA-N 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
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- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229930008407 benzylideneacetone Natural products 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
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- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
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- 239000000395 magnesium oxide Substances 0.000 description 2
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- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- 229950003621 butoxylate Drugs 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- VBVAVBCYMYWNOU-UHFFFAOYSA-N coumarin 6 Chemical compound C1=CC=C2SC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 VBVAVBCYMYWNOU-UHFFFAOYSA-N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical group C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- ZKYQRJXGGLVQML-UHFFFAOYSA-N iridium(3+);2-phenylpyridine Chemical compound [Ir+3].C1=CC=CC=C1C1=CC=CC=N1 ZKYQRJXGGLVQML-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- 229940031993 lithium benzoate Drugs 0.000 description 1
- LDJNSLOKTFFLSL-UHFFFAOYSA-M lithium;benzoate Chemical compound [Li+].[O-]C(=O)C1=CC=CC=C1 LDJNSLOKTFFLSL-UHFFFAOYSA-M 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- DSWNRHCOGVRDOE-UHFFFAOYSA-N n,n-dimethylmethanimidamide Chemical compound CN(C)C=N DSWNRHCOGVRDOE-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- UNJZLNFHHINVOB-UHFFFAOYSA-N n-naphthalen-1-ylnaphthalen-2-amine Chemical compound C1=CC=C2C(NC=3C=C4C=CC=CC4=CC=3)=CC=CC2=C1 UNJZLNFHHINVOB-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- GKROKAVBUIADBS-UHFFFAOYSA-N phenanthrene-2-carbaldehyde Chemical compound C1=CC=C2C3=CC=C(C=O)C=C3C=CC2=C1 GKROKAVBUIADBS-UHFFFAOYSA-N 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003967 siloles Chemical class 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- FVRNDBHWWSPNOM-UHFFFAOYSA-L strontium fluoride Chemical compound [F-].[F-].[Sr+2] FVRNDBHWWSPNOM-UHFFFAOYSA-L 0.000 description 1
- 229910001637 strontium fluoride Inorganic materials 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical compound CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-N zinc;quinolin-8-ol Chemical compound [Zn+2].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
- C07C211/55—Diphenylamines
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- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09D179/06—Polyhydrazides; Polytriazoles; Polyamino-triazoles; Polyoxadiazoles
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- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/24—Electrically-conducting paints
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- 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
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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Abstract
本發明為一種電荷輸送性清漆,其係含有由式(1)所表示之苯胺寡聚物衍生物所構成之電荷輸送性物質、由式(2)所表示之N,N’-二芳基聯苯胺衍生物所構成之電荷輸送性物質、摻雜劑及有機溶劑。
(式中、R1表示氫、烷基、烯基、炔基、芳基或雜芳基,R2~R7表示氫、鹵素、硝基、氰基、胺基、醛基、羥基、硫基、磺酸基、羧酸基、烷基、烯基、炔基、芳基、雜芳基、-NHY1、-NY2Y3、-C(O)Y4、-OY5、-SY6、-SO3Y7、-C(O)OY8、-OC(O)Y9、-C(O)NHY10或-C(O)NY11Y12基)
(式中,R8~R15表示氫、烷基、烯基或炔基,Ar1及Ar2
表示式(3)或(4)所示之基。)
Description
本發明係關於電荷輸送性清漆,詳細而言,關於可賦予透明性與電荷輸送性皆優,在適用於有機電致發光(以下,稱為有機EL)元件時能實現高亮度之薄膜的電荷輸送性清漆。
本發明者等已提出從使用由低分子苯胺寡聚物化合物所構成之電荷輸送性物質之有機溶劑系統之電荷輸送性清漆所得之電荷輸送性薄膜係可展現優良電致發光元件特性(參考專利文獻1)。於專利文獻1記載之電荷輸送性清漆中,構成電荷輸送性材料之低分子苯胺寡聚物化合物係在分子內具有相同重複單位構造,且具有其共軛系統越伸長則越著色,並在作成電荷輸送性薄膜時可視領域之吸收變得越大之性質。
周知電荷輸送性薄膜之著色會導致有機EL元件之色純度及色再現性低下。此外,此著色在3色發光法、白色法及色轉換法等之有機EL顯示器之各種全彩化技術中亦成為問題,在穩定生產有機EL元件時則成為顯
著之障礙。因此,期望有機EL元件之電荷輸送性薄膜在可視領域下之穿透率高,且具有高透明性。
有鑑於此點,本發明者等已發現藉由使用切斷一部分分子內之共軛系統之苯胺寡聚物化合物,或一部分包含由與苯胺單位相異之重複單位構造所構成之共軛系統之苯胺寡聚物化合物,而可取得在可視領域下之著色受到抑制且透明性優異之電荷輸送性薄膜(參考專利文獻2),但為了提昇光取出效率等,故逐漸期望更高透明性之薄膜,且具備專利文獻2記載之薄膜之有機EL元件在元件特性或壽命性能等之點上仍存有改善之餘地。
[專利文獻1]日本特開2002-151272號公報
[專利文獻2]國際公開第2008/032616號
[專利文獻3]日本特開平10-088123號公報
本發明係有鑑於此種情勢所完成者,以提供可賦予具有高透明性與高電荷輸送性,在適用於有機EL元件時能發揮良好元件特性之電荷輸送性薄膜之電荷輸送性清漆為目的。
本發明者等為了達成上述目的經過重複精心探討之結果,發現從包含由規定之苯胺寡聚物衍生物所構成之電荷輸送性物質、由規定之N,N’-二芳基聯苯胺衍生物所構成之電荷輸送性物質及摻雜劑之電荷輸送性清漆,可取得一併持有高透明性與高電荷輸送性之薄膜,並同時發現將該薄膜適用於有機EL元件時能實現優異亮度特性,進而完成本發明。尚且,專利文獻3中雖揭示使用N,N’-二苯基聯苯胺作為電洞輸送材料之有機EL元件,但並未揭示藉由使用該化合物而可取得透明性優異之薄膜。
即,本發明係提供下述電荷輸送性清漆。
1.一種電荷輸送性清漆,其特徵為包含由式(1)所表示之苯胺寡聚物衍生物所構成之電荷輸送性物質、由式(2)所表示之N,N’-二芳基聯苯胺衍生物所構成之電荷輸送性物質、摻雜劑及有機溶劑。
(式中,R16~R25係各自獨立表示氫原子、碳數1~20之烷基、碳數2~20之烯基或碳數2~20之炔基,X1及X2係各自獨立表示氫原子、碳數1~20之烷基、碳數2~20之烯基、碳數2~20之炔基、二苯基胺基、1-萘基苯基胺基、2-萘基苯基胺基、二(1-萘基)胺基、二(2-萘基)胺基或1-萘基-2-萘基胺基。)]
2.一種電荷輸送性薄膜,其係使用如1之電荷輸送性清漆所製成者。
3.一種電子裝置,其係具有2之電荷輸送性薄膜。
4.一種有機EL元件,其係具有2之電荷輸送性薄膜。
5.如4之有機EL元件,其中電荷輸送性薄膜為電洞注入層或電洞輸送層。
6.一種電荷輸送性薄膜之製造方法,其特徵為將如1之電荷輸送性清漆塗佈於基材上並燒成。
7.一種有機EL元件之製造方法,其特徵為使用如2之電荷輸送性薄膜。
藉由使用本發明之電荷輸送性清漆,可取得在可視領域下之吸收受到抑制之高透明性之電荷輸送性薄膜。藉由使用此薄膜,可不使電場發光之光,或穿透濾色器之光之色純度降低,而可確保元件之色再現性,故可大幅賦予從發光層往外部之光取出效率之提升,且變得可謀求有機EL元件之小型化或低驅動電壓化等。
又,藉由使用本發明之電荷輸送性清漆,可取得具備高透明性及導電性之電荷輸送性薄膜,尤其藉由將此薄膜適用於有機EL元件之電洞注入層時,可取得具有優異亮度特性之有機EL元件。
更進一步,由本發明之電荷輸送性清漆所得之薄膜係亦能使用作為防帶電膜或有機薄膜太陽能電池之陽極緩衝層等。
本發明之電荷輸送性清漆包含由式(1)所表示之苯胺寡聚物衍生物所構成之電荷輸送性物質。在此,電荷輸送性係與導電性為同義,亦與電洞輸送性為同義。電荷輸送性物質可為其自身即具有電荷輸送性者,亦可為在與電子受容性物質一同使用時具有電荷輸送性者。尚且,電荷輸送性清漆可為其自身即具有電荷輸送性者,亦可為由其所得之固形膜為具有電荷輸送性者。
R1係各自獨立表示氫原子、可經Z1取代之碳數1~20之烷基、碳數2~20之烯基或碳數2~20之炔基,或可經Z2取代之碳數6~20之芳基或碳數2~20之雜芳基。
碳數1~20之烷基可為直鏈狀、分枝狀、環狀之任一者,作為其具體例,可舉出如甲基、乙基、n-丙基、異丙基、n-丁基、異丁基、s-丁基、t-丁基、n-戊基、n-己基、n-庚基、n-辛基、n-壬基、n-癸基等之碳數1~20之直鏈狀或分枝狀烷基;環丙基、環丁基、環戊基、環己基、環庚基、環辛基、環壬基、環癸基、雙環丁基、雙環戊基、雙環己基、雙環庚基、雙環辛基、雙環壬基、雙環癸基等之碳數3~20之環狀烷基。
作為碳數2~20之烯基之具體例,可舉出如乙烯基、n-1-丙烯基、n-2-丙烯基、1-甲基乙烯基、n-1-丁烯基、n-2-丁烯基、n-3-丁烯基、2-甲基-1-丙烯基、2-甲基-2-丙烯基、1-乙基乙烯基、1-甲基-1-丙烯基、1-甲基-2-丙烯基、n-1-戊烯基、n-1-癸烯基、n-1-二十碳烯基等。
作為碳數2~20之炔基之具體例,可舉出如乙炔基、n-1-丙炔基、n-2-丙炔基、n-1-丁炔基、n-2-丁炔
基、n-3-丁炔基、1-甲基-2-丙炔基、n-1-戊炔基、n-2-戊炔基、n-3-戊炔基、n-4-戊炔基、1-甲基-n-丁炔基、2-甲基-n-丁炔基、3-甲基-n-丁炔基、1,1-二甲基-n-丙炔基、n-1-己炔基、n-1-癸炔基、n-1-十五碳炔基、n-1-二十碳炔基等。
作為碳數6~20之芳基之具體例,可舉出如苯基、1-萘基、2-萘基、1-蒽基、2-蒽基、9-蒽基、1-菲基、2-菲基、3-菲基、4-菲基、9-菲基等。
作為碳數2~20之雜芳基之具體例,可舉出如2-噻吩基、3-噻吩基、2-呋喃基、3-呋喃基、2-噁唑基、4-噁唑基、5-噁唑基、3-異噁唑基、4-異噁唑基、5-異噁唑基、2-噻唑基、4-噻唑基、5-噻唑基、3-異噻唑基、4-異噻唑基、5-異噻唑基、2-咪唑基、4-咪唑基、2-吡啶基、3-吡啶基、4-吡啶基等。
此等之中,R1係以氫原子、可經Z1取代之碳數1~20之烷基,或可經Z2取代之碳數6~20之芳基為佳,以氫原子、可經Z1取代之碳數1~10之烷基或可經Z2取代之碳數6~14之芳基為較佳,以氫原子、可經Z1取代之碳數1~4之烷基,或可經Z2取代之苯基為更佳,以氫原子為最適宜。尚且,複數之R1可各自為相同亦可為相異。
R2~R7係各自獨立表示氫原子、鹵素原子、硝基、氰基、胺基、醛基、羥基、巰基、磺酸基、羧酸基、可經Z1取代之碳數1~20之烷基、碳數2~20之烯基或碳
數2~20之炔基;可經Z2取代之碳數6~20之芳基或碳數2~20之雜芳基;-NHY1、-NY2Y3、-C(O)Y4、-OY5、-SY6、-SO3Y7、-C(O)OY8、-OC(O)Y9、-C(O)NHY10或-C(O)NY11Y12基。
Y1~Y12係各自獨立表示可經Z1取代之碳數1~20之烷基、碳數2~20之烯基或碳數2~20之炔基,或可經Z2取代之碳數6~20之芳基或碳數2~20之雜芳基。
作為鹵素原子,可舉出如氟原子、氯原子、溴原子、碘原子等。
作為R2~R7及Y1~Y12所表示之烷基、烯基、炔基、芳基及雜芳基,可舉出與作為R1所例示者為相同者。
此等之中,R2~R5係以氫原子、鹵素原子、可經Z1取代之碳數1~10之烷基或可經Z2取代之碳數6~14之芳基為佳,以氫原子、鹵素原子或可經Z1取代之碳數1~10之烷基為較佳,以氫原子或鹵素原子為更佳,以全部皆為氫原子為最適宜。
又,R6及R7係以氫原子、鹵素原子、可經Z1取代之碳數1~10之烷基、可經Z2取代之碳數6~14之芳基或可經Z2取代之二苯基胺基(Y2及Y3為可經Z2取代之苯基之-NY2Y3基)為佳,以氫原子、鹵素原子、可經Z1取代之碳數1~10之烷基或可經Z2取代之二苯基胺基為較佳,以氫原子或可經Z2取代之二苯基胺基更佳,以氫原子或二苯基胺基為更較佳。尤其,以R6及R7皆為氫原子或二苯基胺基為最適宜。
式(1)中,n表示2~20之整數,由提高苯胺寡聚物衍生物之溶解性之觀點,以10以下為佳,較佳為8以下,更佳為6以下,由提高取得之薄膜之電荷輸送性之觀點,以3以上為佳,較佳為4以上,更佳為5以上。
尚且,R1~R7及Y1~Y12之烷基、烯基及炔基係可被身為鹵素原子、硝基、氰基、胺基、醛基、羥基、巰基、磺酸基、羧酸基、或可經Z3取代之碳數6~20之芳基或碳數2~20之雜芳基之Z1所取代,R1~R7及Y1~Y12之芳基及雜芳基係可被身為鹵素原子、硝基、氰基、胺基、醛基、羥基、巰基、磺酸基、羧酸基、或可經Z3取代之碳數1~20之烷基、碳數2~20之烯基或碳數2~20之炔基之Z2所取代,此等之基更亦可被身為鹵素原子、硝基、氰基、胺基、醛基、羥基、巰基、磺酸基或羧酸基之Z3所取代(作為鹵素原子,可舉出上述相同者)。
尤其,R1~R7及Y1~Y12中,Z1係以鹵素原子或可經Z3取代之碳數6~20之芳基為佳,以鹵素原子或可經Z3取代之苯基為較佳,以不存在(即,非取代)為最適宜。
Z2係以鹵素原子或可經Z3取代之碳數1~20之烷基為佳,以鹵素原子或可經Z3取代之碳數1~4之烷基為較佳,以不存在(即,非取代)為最適宜。
Z3係以鹵素原子為佳,以氟為較佳,以不存在(即,非取代)為最適宜。
R1~R7及Y1~Y12所表示之烷基、烯基及炔基之
碳數係以10以下為佳,較佳為6以下,更佳為4以下。又,芳基及雜芳基之碳數係以14以下為佳,較佳為10以下,更佳為6以下。
本發明之電荷輸送性清漆包含由式(2)所表示之N,N’-二芳基聯苯胺衍生物所構成之電荷輸送性物質。
R8~R15係各自獨立表示氫原子、碳數1~20之烷基、碳數2~20之烯基或碳數2~20之炔基。作為此等烷基、烯基及炔基,可舉出與作為R1所例示者為相同者。
此等之中,R8~R15係以氫原子或碳數1~20之烷基為佳,以氫原子或碳數1~10之烷基為較佳,以氫原子或碳數1~6之烷基為更佳,以氫原子或碳數1~4之烷基為更較佳,以全部係氫原子為最適宜。
式(1)中,Ar1及Ar2係各自獨立表示式(3)或(4)所表示之基。
式(3)及(4)中,R16~R25係各自獨立表示氫原子、碳數1~20之烷基、碳數2~20之烯基或碳數2~20之炔基。此等之中,R16~R25係以氫原子或碳數1~20之烷基為佳,以氫原子或碳數1~10之烷基為較佳,以氫原子或碳數1~6之烷基為更佳,以氫原子或碳數1~4之烷基為更較佳,以全部係氫原子為最適宜。
X1及X2係各自獨立表示氫原子、碳數1~20之烷基、碳數2~20之烯基、碳數2~20之炔基、二苯基胺基、1-萘基苯基胺基、2-萘基苯基胺基、二(1-萘基)胺基、二(2-萘基)胺基或1-萘基-2-萘基胺基。此等之中,X1及X2係以氫原子、碳數1~20之烷基、二苯基胺基、1-萘基苯基胺基、2-萘基苯基胺基、二(1-萘基)胺基、二(2-萘基)胺基或1-萘基-2-萘基胺基為佳,以氫原子、二苯基胺基、1-萘基苯基胺基、2-萘基苯基胺基、二(1-萘基)胺基、二(2-萘基)胺基或1-萘基-2-萘基胺基為較佳,以氫原子或二苯基胺基為更佳,以全部係氫原子為最適宜。
尚且,R8~R25、X1及X2所表示之烷基、烯基及炔基之碳數係以10以下為佳,較佳為6以下,更佳為
4以下。
本發明中所用之苯胺寡聚物衍生物及N,N’-二芳基聯苯胺衍生物之分子量,通常為200~5,000,由提高此等衍生物之溶解性之觀點,以3,000以下為佳,較佳為2,000以下。
本發明中,苯胺寡聚物衍生物係可使用市售品,亦可使用以公知之方法所合成者。合成法並無特別限定,例如可舉出在日本化學協會會報(Bulletin of Chemical Society of Japan)(1994年、第67卷、pp.1749-1752)、合成金屬(Synthetic Metals)(1997年、第84卷、pp.119-120)、國際公開第2008/032617號、國際公開第2008-032616號、國際公開第2008-129947號等中記載之方法。
另一方面,N,N’-二芳基聯苯胺衍生物係同樣可使用市售品,亦可使用以公知之方法(例如,Thin Solid Films,520(24),pp.7157-7163(2012)中記載之方法)或後述之方法所合成者,在任一之情況皆係以使用在調製電荷輸送性清漆之前,藉由再結晶或蒸鍍法等進行純化者為佳。藉由使用經純化者,能更提高具備由該清漆所得之薄膜之有機EL元件之特性。
使用再結晶進行純化時,溶劑係可使用例如、1,4-二噁烷、四氫呋喃等。
式(2)所表示之N,N’-二芳基聯苯胺衍生物係例如可使式(5)所表示之聯苯基化合物與式(6)所表
示之芳香族胺化合物進行反應而得。
(式中,R8~R15係與上述相同。Ar3係與上述Ar1及Ar2相同。Y表示氯原子、溴原子、碘原子等之鹵素原子。)
作為式(5)所表示之聯苯基化合物,可舉出如4,4’-二氯聯苯基、4,4’-二溴聯苯基、4,4’-二碘聯苯基、4-氯-4’-溴聯苯基、4-氯-4’-碘聯苯基、4-溴-4’-碘聯苯基等。
作為式(6)所表示之芳香族胺化合物,可舉出如苯胺、1-萘基胺、4-(二苯基胺基)苯胺、4-二苯基胺基-1-萘基胺等。
式(5)所表示之聯苯基化合物與式(6)所表示之芳香族胺化合物之添加比,可設成相對於聯苯基化合物1mol,芳香族胺化合物為1.8~4.0mol程度,以2.0~3.0mol程度為適宜。
作為上述反應所使用之觸媒,例如可舉出氯化銅、溴化銅、碘化銅等之銅觸媒、Pd(PPh3)4(肆(三苯基膦)鈀)、Pd(PPh3)2Cl2(雙(三苯基膦)二氯鈀)、Pd(dba)2(雙(亞苄基丙酮)鈀)、Pd2(dba)3(參(亞苄基丙酮)二鈀)、Pd(P-t-Bu3)2(雙(三(t-丁基膦)
鈀))等之鈀觸媒等。此等觸媒可單獨使用1種,亦可將2種以上組合使用。又,此等觸媒係亦可與適宜配位子一同使用。
觸媒之使用量,在相對於聯苯基化合物1mol,可設成0.001~0.5mol程度,以0.01~0.2mol程度為適宜。
上述反應係亦可在溶劑中進行。在使用溶劑時,只要係不對反應產生不良影響者,即可使用任何溶劑。作為溶劑之具體例,可舉出脂肪族烴類(戊烷、n-己烷、n-辛烷、n-癸烷、十氫萘等)、鹵化脂肪族烴類(氯仿、二氯甲烷、二氯乙烷、四氯化碳等)、芳香族烴類(苯、硝基苯、甲苯、o-茬、m-茬、p-茬、均三甲苯等)、鹵化芳香族烴類(氯苯、溴苯、o-二氯苯、m-二氯苯、p-二氯苯等)、醚類(二乙基醚、二異丙基醚、t-丁基甲基醚、四氫呋喃、二噁烷、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷等)、酮類(丙酮、甲基乙基酮、甲基異丁基酮、二-n-丁基酮、環己酮等)、醯胺類(N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等)、內醯胺及內酯類(N-甲基吡咯啶酮、γ-丁內酯等)、脲類(N,N-二甲基四氫咪唑酮、四甲基脲等)、亞碸類(二甲基亞碸、環丁碸等)、腈類(乙腈、丙腈、丁腈等)等。此等溶劑可單獨使用1種,亦可將2種以上混合使用。
反應溫度係適宜設定在所使用之溶劑之融點至沸點為止之範圍內即可,尤其係以0~200℃程度為佳,
以20~150℃為較佳。
反應結束後係依據常法進行後處理,而可取得目的之N,N’-二芳基聯苯胺衍生物。
作為本發明中可適宜使用之苯胺寡聚物衍生物,可舉出如以下者,但並不受限於此等。
作為本發明中可適宜使用之N,N’-二芳基聯苯胺衍生物,可舉出如以下者,但不受限於此等。
本發明之電荷輸送性清漆包含摻雜劑。摻雜劑只要可溶解於清漆中使用之至少1種溶劑中者,即無特別限定,可使用無機系之摻雜劑、有機系之摻雜劑之任一者。
作為無機系之摻雜劑,可舉出如氯化氫、硫酸、硝酸、磷酸等之無機酸;氯化鋁(III)(AlCl3)、四氯化鈦(IV)(TiCl4)、三溴化硼(BBr3)、三氟化硼醚錯合物(BF3‧OEt2)、氯化鐵(III)(FeCl3)、氯化銅(II)(CuCl2)、五氯化銻(V)(SbCl5)、五氟化銻(V)(SbF5)、五氟化砷(V)(AsF5)、五氟化磷(PF5)、參(4-溴苯基)鋁六氯銻酸鹽(TBPAH)等之金屬鹵化物;Cl2、Br2、I2、ICl、ICl3、IBr、IF4等之鹵素;磷鉬酸、磷鎢酸等之異性聚合酸等。
作為有機系之摻雜劑,可舉出如苯磺酸、對甲苯磺酸(tosic acid)、p-苯乙烯磺酸、2-萘磺酸、4-羥基苯磺酸、5-磺柳酸、p-十二基苯磺酸、二己基苯磺酸、2,5-二己基苯磺酸、二丁基萘磺酸、6,7-二丁基-2-萘磺酸、十二基萘磺酸、3-十二基-2-萘磺酸、己基萘磺酸、4-己基-1-萘磺酸、辛基萘磺酸、2-辛基-1-萘磺酸、己基萘磺酸、7-己基-1-萘磺酸、6-己基-2-萘磺酸、二壬基萘磺酸、2,7-二壬基-4-萘磺酸、二壬基萘二磺酸、2,7-二壬基-4,5-萘二磺酸、國際公開第2005/000832號中記載之1,4-苯并二噁烷二磺酸化合物、國際公開第2006/025342號中記載之芳基磺酸化合物、國際公開第2009/096352號
中記載之芳基磺酸化合物、聚苯乙烯磺酸等之芳基碸化合物;10-樟腦磺酸等之非芳基碸化合物;7,7,8,8-四氰基醌二甲烷(TCNQ)、2,3-二氯-5,6-二氰基-1,4-苯醌(DDQ)等之有機氧化劑。此等無機系及有機系之摻雜劑係可單獨使用1種,亦可將2種以上組合使用。
此等之中,以芳基磺酸化合物為佳,以式(7)所表示之芳基磺酸化合物為較佳。
(式中,M表示氧原子,A表示萘環或蒽環,B表示2~4價之全氟聯苯基,p表示與A結合之磺酸基數,且為滿足1≦p≦4之整數,q表示B與M之結合數,且為滿足2~4之整數。)
作為本發明中可適宜使用之摻雜劑,可舉出如以下者,但不受限於此等。
本發明中,在物質量比(mol比)下,相對於式(1)所表示之苯胺寡聚物衍生物1而言,可將式(2)所表示之N,N’-二芳基聯苯胺衍生物設在0.01~100程度,
較佳設在0.1~30程度,更佳設在0.8~20程度,藉此可再現性良好地取得在使用於有機EL元件時可賦予高亮度之電荷輸送性薄膜。即,本發明之電荷輸送性清漆中式(2)所表示之N,N’-二芳基聯苯胺衍生物之物質量(MH2)對式(1)所表示之苯胺寡聚物衍生物之物質量(MH1)之比為滿足0.01≦MH2/MH1≦100,較佳滿足0.1≦MH2/MH1≦30,更佳滿足0.8≦MH2/MH1≦20。
又,本發明中,在物質量比(mol比)下,相對於電荷輸送性物質(即為式(1)所表示之苯胺寡聚物衍生物及式(2)所表示之N,N’-二芳基聯苯胺衍生物。以下相同。)1而言,可將摻雜劑、較佳為芳基磺酸化合物、更佳為式(7)所表示之芳基磺酸化合物、更較佳為式(8)所表示之芳基磺酸化合物設在0.01~100程度,較佳設在0.1~10程度,更佳設在0.3~5程度,藉此可再現性良好地取得在使用於有機EL元件時能賦予高亮度之電荷輸送性薄膜。即,本發明之電荷輸送性清漆中摻雜劑之物質量(MD)對電荷輸送性物質之物質量(MH)之比為滿足0.01≦MD/MH≦100,較佳滿足0.1≦MD/MH≦10,更佳滿足0.3≦MD/MH≦5。
本發明之電荷輸送性清漆中,除上述之苯胺寡聚物衍生物或N,N’-二芳基聯苯胺衍生物以外,尚亦可使用公知之其他電荷輸送性物質。
作為調製本發明之電荷輸送性清漆時所使用之有機溶劑,可使用能良好地溶解電荷輸送性物質及摻雜劑之高溶解性溶劑。作為此般高溶解性溶劑,例如可舉出N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮、1,3-二甲基-2-四氫咪唑酮、二乙二醇單甲基醚等。此等溶劑係可單獨使用1種單獨或可將2種以上混合使用,其使用量在相對於清漆所使用之溶劑全體而言,可設為5~100質量%。尚且,電荷輸送性物質及摻雜劑係以皆完全溶解於上述溶劑中,或成為均勻分散之狀態為佳,以完全溶解為較佳。
又,本發明之電荷輸送性清漆在25℃下具有10~200mPa‧s,尤其係具有35~150mPa‧s之黏度,在常壓(大氣壓)下亦可至少含有一種沸點50~300℃,尤其係150~250℃之高黏度有機溶劑。藉此,清漆之黏度調整變得容易,其結果係變得可因應能再現性良好地賦予高平坦性薄膜所使用之塗佈方法之清漆調製。
作為高黏度有機溶劑,可舉出如環己醇、乙二醇、乙二醇二環氧丙基醚、1,3-辛二醇、二乙二醇、二丙二醇、三乙二醇、三丙二醇、1,3-丁二醇、2,3-丁二醇、1,4-丁二醇、丙二醇、己二醇等,但不受限於此等。此等溶劑可單獨使用1種,亦可將2種以上混合使用。
本發明之清漆所使用之相對於溶劑全體之高黏度有機溶劑之添加比例係以不析出固體之範圍內為佳,只要在不析出固體之範圍內,添加比例係以5~80質量%
為佳。
並且,以提升對基板之濕潤性,溶劑之表面張力之調整、極性之調整、沸點之調整等之目的,相對於清漆所使用之溶劑全體,亦可在1~90質量%,較佳為1~50質量%之比例下混合其他溶劑。
作為其他溶劑,例如可舉出乙二醇單丁基醚、二乙二醇二乙基醚、二乙二醇二甲基醚、二乙二醇單乙基醚乙酸酯、二乙二醇單丁基醚乙酸酯、二丙二醇單甲基醚、丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、二乙二醇單乙基醚、二丙酮醇、γ-丁內酯、乳酸乙酯、乙酸n-己酯等,但不受限於此等。此等溶劑可單獨使用1種或可將2種以上混合使用。
本發明之清漆之黏度係因應所製作之薄膜之厚度或固形分濃度等而適宜設定者,但通常在25℃下為1~50mPa‧s。
又,本發明之電荷輸送性清漆之固形分濃度係考量到清漆之黏度及表面張力等,或製作之薄膜之厚度等而適宜設定者,通常為0.1~10.0質量%程度,若考慮到使清漆塗佈性提升時,較佳為0.5~5.0質量%,更佳為1.0~3.0質量%。
藉由將本發明之電荷輸送性清漆塗佈於基材上並燒成,而可在基材上形成電荷輸送性薄膜。
清漆之塗佈方法並非係受到特別限定者,可舉出如浸漬法、旋轉塗佈法、轉印印刷法、輥塗法、刷塗法、噴墨法、噴霧法等,因應塗佈方法調節清漆之黏度及表面張力為佳。
又,使用本發明之清漆時,燒成環境亦並非係受到特別限定者,不僅在大氣環境下,於氮等之惰性氣體或真空中亦能取得具有均勻成膜面及高電荷輸送性之薄膜。
燒成溫度係考量取得之薄膜之用途、賦予取得薄膜之電荷輸送性之程度等,大致在100~260℃之範圍內適宜設定者,將取得之薄膜使用作為有機EL元件之電洞注入層時,以140~250℃程度為佳,以145~240℃程度為較佳。尚且,於燒成之際,以使其展現較高均勻成膜性,或於基材上使反應進行為目的,亦可附加2段階以上之溫度變化。加熱係使用例如加熱板或烤箱等適當機器施行即可。
電荷輸送性薄膜之膜厚並無特別限定,於有機EL元件內使用作為電洞注入層時,以5~200nm為佳。作為使膜厚變化之方法,則有使清漆中之固形分濃度變化,或使塗佈時之基板上之溶液量變化等之方法。
作為使用本發明之電荷輸送性清漆製造OLED元件時之使用材料或製作方法,可舉出如下述者,但不受限於此
等。
使用之電極基板係以預先進行由洗劑、醇、純水等之液體洗淨使其淨化為佳,例如,陽極基板係以在使用前施行UV臭氧處理、氧-電漿處理等之表面處理為佳。但,陽極材料係將有機物作為主成分時,亦可不施行表面處理。
具有由本發明之電荷輸送性清漆所得之薄膜所構成之電洞注入層之OLED元件之製作方法之例則係如以下所述。
藉由上述之方法,於陽極基板上塗佈本發明之電荷輸送性清漆並燒成,而在電極上製作電洞注入層。將此導入真空蒸鍍裝置內,依序蒸鍍電洞輸送層、發光層、電子輸送層、電子注入層、陰極金屬而作成OLED元件。為了控制發光領域,亦可在任意之層間設置載子阻礙層。
作為陽極材料,可舉出由銦錫氧化物(ITO)、銦鋅氧化物(IZO)所代表之透明電極,以施加有平坦化處理者為佳。亦可使用具有高電荷輸送性之聚噻吩衍生物或聚苯胺衍生物。
作為形成電洞輸送層之材料,可舉出如(三苯基胺)二聚物衍生物(TPD)、N,N’-二(1-萘基)-N,N’-二苯基聯苯胺(α-NPD)、[(三苯基胺)二聚物]螺二聚物(Spiro-TAD)等之三芳基胺類、4,4’,4”-參[3-甲基苯基(苯基)胺基]三苯基胺(m-MTDATA)、4,4’,4”-
參[1-萘基(苯基)胺基]三苯基胺(1-TNATA)等之星爆胺類、5,5”-雙-{4-[雙(4-甲基苯基)胺基]苯基}-2,2’:5’,2”-三聯噻吩(BMA-3T)等之寡聚噻吩類等。
作為形成發光層之材料,可舉出如參(8-羥基喹啉)鋁(III)(Alq3)、雙(8-羥基喹啉)鋅(II)(Znq2)、雙(2-甲基-8-羥基喹啉)(p-苯基酚)鋁(III)(BAlq)及4,4’-雙(2,2-二苯基乙烯基)聯苯基(DPVBi)等,亦可藉由共蒸鍍電子輸送材料或電洞輸送材料與發光性摻雜劑而形成發光層。
作為電子輸送材料,可舉出如Alq3、BAlq、DPVBi、2-(4-聯苯基)-5-(4-t-丁基苯基)-1,3,4-噁二唑(PBD)、三唑衍生物(TAZ)、浴銅靈(bathocuproine)(BCP)、噻咯(silole)衍生物等。
作為發光性摻雜劑,可舉出如喹吖啶酮、紅螢烯、香豆素540、4-(二氰基亞甲基)-2-甲基-6-(p-二甲基胺基苯乙烯基)-4H-吡喃(DCM)、參(2-苯基吡啶)銥(III)(Ir(ppy)3)、(1,10-啡啉)-參(4,4,4-三氟-1-(2-噻吩基)-丁烷-1,3-二酮)銪(III)(Eu(TTA)3phen)等。
作為形成載子阻礙層之材料,可舉出如PBD、TAZ、BCP等。
作為形成電子注入層之材料,可舉出如氧化鋰(Li2O)、氧化鎂(MgO)、氧化鋁(Al2O3)、氟化鋰(LiF)、氟化鈉(NaF)、氟化鎂(MgF2)、氟化鍶
(SrF2)、Liq、Li(acac)、乙酸鋰、安息香酸鋰等。
作為陰極材料,可舉出如鋁、鎂-銀合金、鋁-鋰合金、鋰、鈉、鉀、銫等。
使用本發明之電荷輸送性清漆之PLED元件之製作方法並無特別限定,可舉出如以下之方法。
上述OLED元件製作中,亦可取代電洞輸送層、發光層、電子輸送層、電子注入層之真空蒸鍍操作,藉由依序形成電洞輸送性高分子層、發光性高分子層,而製成具有由本發明之電荷輸送性清漆所形成之電荷輸送性薄膜之PLED元件。具體而言,於陽極基板上塗佈本發明之電荷輸送性清漆,藉由上述之方法製作電洞注入層,並於其上依序形成電洞輸送性高分子層、發光性高分子層後,再蒸鍍陰極電極而作成PLED元件。
作為使用之陰極及陽極材料,可使用與上述OLED元件製作時相同者,亦可施行同樣之洗淨處理、表面處理。
作為電洞輸送性高分子層及發光性高分子層之形成法,可舉出如在電洞輸送性高分子材料或發光性高分子材料、或於此等中添加摻雜劑之材料中添加溶劑使其溶解或均勻分散並塗佈於電洞注入層或電洞輸送性高分子層之上後,各自進行燒成而成膜之方法。
作為電洞輸送性高分子材料,可舉出如聚[(9,9-二己基茀-2,7-二基)-co-(N,N’-雙{p-丁基苯基}-1,4-二胺基伸苯基)]、聚[(9,9-二辛基茀-2,7-二基)-
co-(N,N’-雙{p-丁基苯基}-1,1’-亞聯苯基-4,4-二胺)]、聚[(9,9-雙{1’-戊烯-5’-基}茀-2,7-二基)-co-(N,N’-雙{p-丁基苯基}-1,4-二胺基伸苯基)]、受聚倍半矽氧烷封端之聚[N,N’-雙(4-丁基苯基)-N,N’-雙(苯基)-聯苯胺]、聚[(9,9-貳二辛基茀-2,7-二基)-co-(4,4’-(N-(p-丁基苯基))二苯基胺)]等。
作為發光性高分子材料,可舉出如聚(9,9-二烷基茀)(PDAF)等之聚茀衍生物、聚(2-甲氧基-5-(2’-乙基己氧基)-1,4-苯基乙烯)(MEH-PPV)等之聚苯基乙烯衍生物、聚(3-烷基噻吩)(PAT)等之聚噻吩衍生物、聚乙烯基咔唑(PVCz)等。
作為溶劑,可舉出如甲苯、茬、氯仿等,作為溶解或均勻分散法,可舉出如攪拌、加熱攪拌、超音波分散等之方法。
塗佈方法並非係受到特別限定者,可舉出如噴墨法、噴霧法、浸漬法、旋轉塗佈法、轉印印刷法、輥塗法、刷塗法等。尚且,塗佈係以在氮、氬等之惰性氣體下進行為佳。
作為進行燒成之方法,可舉出在惰性氣體下或真空中,以烤箱或加熱板進行加熱之方法。
以下,例舉實施例及比較例,更具體地說明本發明,但本發明並非係受到下述實施例所限定者。尚
且,使用之裝置係如以下所述。
(1)1H-NMR測量:Varian製 高分解能核磁共振裝置
(2)基板洗淨:長州產業(股)製 基板洗淨裝置(減壓電漿方式)
(3)清漆之塗佈:Mikasa(股)製 旋轉塗佈器MS-A100
(4)膜厚測量:(股)小坂研究所製 微細形狀測量機Surfcorder ET-4000
(5)穿透率測量:(股)島津製作所製 可視紫外線吸收光譜測量裝置UV-3100PC
(6)EL元件之製作:長州產業(股)製 多機能蒸鍍裝置系統C-E2L1G1-N
(7)EL元件之亮度等之測量:(有)Tech World製 I-V-L測量系統
於4,4’-二胺基二苯基胺10.00g(50.19
mmol)、4-溴三苯基胺34.17g(105.40mmol)及若100g之混合懸濁液中添加肆(三苯基膦)鈀0.5799g(0.5018mmol)及t-丁氧基鈉10.13g(105.40mmol),在氮下以130℃攪拌14小時。
其後,過濾反應混合液,對此濾液添加飽和食鹽水並施行分液處理後,使用1,4-二噁烷使從有機層餾除溶劑而得之固體進行再結晶,而得到苯胺衍生物A(收量:22.37g、收率:65%)。
於氮環境下,對已完好乾燥之1-萘酚-3,6-二磺酸鈉11.0g(31.59mmol)依序添加全氟聯苯基4.797g(14.36mol)、碳酸鉀4.167g(30.15mol)及N,N-二甲基甲醯胺100mL,以氮取代反應系統後,在內溫100℃下攪拌6小時。
放置冷卻至室溫後,為了使反應後析出之芳基磺酸C再溶解,更添加N,N-二甲基甲醯胺500mL,在室溫下攪拌90分鐘。攪拌結束後,過濾此溶液而去除碳酸鉀殘渣,並進行減壓濃縮。並且為了去除殘留之雜質,對殘渣添加甲醇100mL,在室溫下攪拌30分鐘。攪拌結束後,
過濾懸濁溶液,而過濾取得過濾物。對過濾物添加超純水300mL使其溶解,藉由使用陽離子交換樹脂DOWEX 650C(陶氏化學公司製、H型約200mL、蒸餾溶劑:超純水)之管柱層析法而進行離子交換。
在減壓下濃縮乾燥固化pH1以下之分餾,在減壓下乾燥固化殘渣而得到芳基磺酸C(收量:11g、收率:85%)。
於氮環境下,使合成例1中製成之苯胺衍生物A0.029g(0.042mmol)、N,N’-二苯基聯苯胺(東京化成工業(股))0.189g(0.563mmol)及合成例2中製成之芳基磺酸C0.282g(0.313mmol)之混合物溶解於1,3-二甲基-2-四氫咪唑酮17.5g。其後,添加環己醇3.5g及丙二醇3.5g,再進行攪拌。使用孔徑0.2μm之PTFE製濾器過濾取得之溶液,而得到電荷輸送性清漆。尚且,N,N’-二苯基聯苯胺係使用1,4-二噁烷進行再結晶,且在減壓下經過完好乾燥後使用於清漆之調製。
除了將苯胺衍生物A、N,N’-二苯基聯苯胺及芳基磺酸C之使用量分別改為0.056g(0.082mmol)、0.166g(0.493mmol)及0.278g(0.308mmol)(實施例1-
2);0.083g(0.121mmol)、0.143g(0.425mmol)及0.274g(0.303mmol)(實施例1-3);0.109g(0.159mmol)、0.121g(0.359mmol)及0.270g(0.299mmol)(實施例1-4);0.054g(0.078mmol)、0.092g(0.274mmol)及0.354g(0.392mmol)(實施例1-5);0.071g(0.104mmol)、0.078g(0.233mmol)及0.351g(0.388mmol)(實施例1-6);以及0.088g(0.128mmol)、0.065g(0.192mmol)及0.347g(0.385mmol)(實施例1-7)以外,其他係以與實施例1-1相同之方法而調製成電荷輸送性清漆。
在氮環境下,使依照國際公開第2008/032616號記載之方法製成之式(9)所表示之N,N’-二芳基聯苯胺衍生物B 0.189g(0.345mmol)及芳基磺酸C 0.311g(0.345mmol)之混合物溶解於1,3-二甲基-2-四氫咪唑酮17.5g。其後,添加環己醇3.5g及丙二醇3.5g再進行攪拌。使用孔徑0.2μm之PTFE製濾器過濾取得之溶液,而得到電荷輸送性清漆。
在氮環境下,使苯胺衍生物A0.031g(0.045mmol)、N,N’-二芳基聯苯胺衍生物B0.166g(0.303mmol)及芳基磺酸C0.304g(0.336mmol)之混合物溶解於1,3-二甲基-2-四氫咪唑酮17.5g。其後,添加環己醇3.5g及丙二醇3.5g再進行攪拌。使用孔徑0.2μm之PTFE製濾器過濾取得之溶液,而得到電荷輸送性清漆。
雖使用N,N’-二苯基聯苯胺0.742g、1,3-二甲基-2-四氫咪唑酮17.5g、環己醇3.5g及丙二醇3.5g嚐試調製成清漆,但清漆為懸濁而無法取得形成有機EL元件用之電荷輸送性薄膜所能使用之均勻清漆。
使用旋轉塗佈器將實施例1-1~1-7及比較例1-1~1-2中取得之清漆分別塗佈於石英基板後,在大氣中以50℃乾燥5分鐘,再以230℃燒成15分鐘,而於石英基板上形成膜厚30nm之均勻薄膜。尚且,石英基板係使用電漿洗淨裝置(150W、30秒間)去除表面上之雜質後再予以使用者。
測量製成之薄膜之穿透率。穿透率係掃瞄可見光領域之波長400~800nm。將400、500、600、700及
800nm處之穿透率、以及400~800nm之平均穿透率展示於表1。
如表1所示般,比起使用將共軛系統被切斷之苯胺寡聚物化合物含有作為電荷輸送性物質之清漆(比較例1-1~1-2)而製成之薄膜,使用實施例1-1~1-7之電荷輸送性清漆所製成之薄膜在可視領域下顯示較高之穿透率。
使用旋轉塗佈器將實施例1-1中取得之清漆塗佈於ITO基板後,以50℃乾燥5分鐘,並且在大氣環境下,以230℃燒成15分鐘,而在ITO基板上形成30nm之均勻薄膜。ITO基板係使用於表面上銦錫氧化物(ITO)圖型化成膜厚150nm之25mm×25mm×0.7t之玻璃基板,且在使
用前藉由O2電漿洗淨裝置(150W、30秒間)去除表面上之雜質者。
其次,使用蒸鍍裝置(真空度1.0×10-5Pa),於對形成有薄膜之ITO基板上依序層合N,N’-二(1-萘基)-N,N’-二苯基聯苯胺(α-NPD)、參(8-羥基喹啉)鋁(III)(Alq3)、氟化鋰、及鋁之薄膜,而取得有機EL元件。此時,蒸鍍速率係分別在α-NPD、Alq3及鋁時為0.2nm/秒、在氟化鋰時為0.02nm/秒之條件下進行,膜厚係分別作成30nm、40nm、0.5nm及120nm。
尚且,為了防治因空氣中之氧、水等之影響所造成之特性劣化,有機EL元件係在藉由密封基板密封後,始評價其之特性。密封係依據以下之順序施行。
在氧濃度2ppm以下、露點-85℃以下之氮環境中,在密封基板之間收納有機EL元件,並藉由接著材料(Nagase Chemtex(股)製XNR5516Z-B1)貼合密封基板。此時,將捕水劑(Dynic(股)製HD-071010W-40)與有機EL元件一同地收納於密封基板內。對於已貼合之密封基板,照射UV光(波長:365nm、照射量:6,000mJ/cm2)後,在80℃下施行1小時退火處理而使接著材料硬化。
除取代實施例1-1中取得之清漆,而分別改為使用實施例1-2~1-7、比較例1-1~1-2中取得之清漆以外,以與
實施例3-1相同之方法製成有機EL元件。
除取代使用清漆形成薄膜,改為使用N,N’-二苯基聯苯胺為蒸鍍源之蒸鍍法(蒸鍍速率0.2nm/秒),於ITO基板上形成僅由N,N’-二苯基聯苯胺所構成之30nm之均勻薄膜以外,以與實施例3-1相同之方法製成有機EL元件。
測量製成之有機EL元件在驅動電壓5V下之電流密度及亮度。其結果係如表2所示。
如表2所示,比起比較例之元件,實施例之有機EL元件展現較高之亮度。
Claims (7)
- 一種電荷輸送性清漆,其特徵為包含由式(1)所表示之苯胺寡聚物衍生物所構成之電荷輸送性物質、由式(2)所表示之N,N’-二芳基聯苯胺衍生物所構成之電荷輸送性物質、摻雜劑及有機溶劑;
- 一種電荷輸送性薄膜,其係使用如請求項1之電荷輸送性清漆而製成者。
- 一種電子裝置,其係具有如請求項2之電荷輸送性薄膜。
- 一種有機電致發光元件,其係具有如請求項2之電 荷輸送性薄膜。
- 如請求項4之有機電致發光元件,其中前述電荷輸送性薄膜為電洞注入層或電洞輸送層。
- 一種電荷輸送性薄膜之製造方法,其特徵為在基材上塗佈如請求項1之電荷輸送性清漆並燒成。
- 一種有機電致發光元件之製造方法,其特徵為使用如請求項2之電荷輸送性薄膜。
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