TWI654190B - Charge transport paint, charge transport film, method of producing the same, and organic electroluminescence device and method of producing the same - Google Patents
Charge transport paint, charge transport film, method of producing the same, and organic electroluminescence device and method of producing the sameInfo
- Publication number
- TWI654190B TWI654190B TW104122703A TW104122703A TWI654190B TW I654190 B TWI654190 B TW I654190B TW 104122703 A TW104122703 A TW 104122703A TW 104122703 A TW104122703 A TW 104122703A TW I654190 B TWI654190 B TW I654190B
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- charge transporting
- bis
- carbon atoms
- paint
- Prior art date
Links
- 239000003973 paint Substances 0.000 title claims abstract description 52
- 238000000034 method Methods 0.000 title claims description 49
- 238000005401 electroluminescence Methods 0.000 title claims description 8
- 239000000126 substance Substances 0.000 claims abstract description 43
- 239000002019 doping agent Substances 0.000 claims abstract description 33
- 239000003960 organic solvent Substances 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 49
- 239000000758 substrate Substances 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 30
- 239000000463 material Substances 0.000 claims description 25
- 238000002347 injection Methods 0.000 claims description 24
- 239000007924 injection Substances 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 239000011964 heteropoly acid Substances 0.000 claims description 11
- 230000005525 hole transport Effects 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 abstract description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 9
- 229960005544 indolocarbazole Drugs 0.000 abstract 1
- 239000010408 film Substances 0.000 description 54
- -1 nitro, cyano, amino, dimethylamino Chemical group 0.000 description 54
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 22
- 239000002904 solvent Substances 0.000 description 21
- 238000000576 coating method Methods 0.000 description 18
- 239000000203 mixture Substances 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 229910052787 antimony Inorganic materials 0.000 description 13
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 13
- 241000208340 Araliaceae Species 0.000 description 12
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 12
- 235000003140 Panax quinquefolius Nutrition 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229910052797 bismuth Inorganic materials 0.000 description 12
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 12
- 235000008434 ginseng Nutrition 0.000 description 12
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 12
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 229910052782 aluminium Inorganic materials 0.000 description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 125000001153 fluoro group Chemical group F* 0.000 description 9
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 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 8
- 229920000642 polymer Polymers 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 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 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- 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 5
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910052707 ruthenium Inorganic materials 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 239000004922 lacquer Substances 0.000 description 4
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
- 239000002861 polymer material Substances 0.000 description 4
- 239000010453 quartz Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- 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
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-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
- MOGTVLAYAVGOJK-UHFFFAOYSA-N 2-[5-(trifluoromethyl)-1h-1,2,4-triazol-3-yl]pyridine Chemical compound FC(F)(F)C1=NNC(C=2N=CC=CC=2)=N1 MOGTVLAYAVGOJK-UHFFFAOYSA-N 0.000 description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- PJVZQNVOUCOJGE-CALCHBBNSA-N chembl289853 Chemical compound N1([C@H]2CC[C@H](O2)N2[C]3C=CC=CC3=C3C2=C11)C2=CC=C[CH]C2=C1C1=C3C(=O)N(C)C1=O PJVZQNVOUCOJGE-CALCHBBNSA-N 0.000 description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- HASCQPSFPAKVEK-UHFFFAOYSA-N dimethyl(phenyl)phosphine Chemical compound CP(C)C1=CC=CC=C1 HASCQPSFPAKVEK-UHFFFAOYSA-N 0.000 description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
- 238000010304 firing Methods 0.000 description 3
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- 125000001624 naphthyl group Chemical group 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000010422 painting Methods 0.000 description 3
- 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 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
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- 125000005504 styryl group Chemical group 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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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- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
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- 239000000395 magnesium oxide Substances 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 2
- VFTLAONLPYVBBL-UHFFFAOYSA-N (2-benzylphenyl)-phenylphosphinic acid Chemical compound OP(=O)(c1ccccc1)c1ccccc1Cc1ccccc1 VFTLAONLPYVBBL-UHFFFAOYSA-N 0.000 description 1
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- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 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
- 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
- 239000003599 detergent Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- ORJMYGVUKICDDG-UHFFFAOYSA-N didecyl(phenyl)phosphane Chemical compound CCCCCCCCCCP(CCCCCCCCCC)C1=CC=CC=C1 ORJMYGVUKICDDG-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
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 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
- 230000008020 evaporation Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- YERGTYJYQCLVDM-UHFFFAOYSA-N iridium(3+);2-(4-methylphenyl)pyridine Chemical compound [Ir+3].C1=CC(C)=CC=C1C1=CC=CC=N1.C1=CC(C)=CC=C1C1=CC=CC=N1.C1=CC(C)=CC=C1C1=CC=CC=N1 YERGTYJYQCLVDM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 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
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([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
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000007788 liquid 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
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- YPJRZWDWVBNDIW-MBALSZOMSA-N n,n-diphenyl-4-[(e)-2-[4-[4-[(e)-2-[4-(n-phenylanilino)phenyl]ethenyl]phenyl]phenyl]ethenyl]aniline Chemical group C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1/C=C/C(C=C1)=CC=C1C(C=C1)=CC=C1\C=C\C(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 YPJRZWDWVBNDIW-MBALSZOMSA-N 0.000 description 1
- NJWJVPXCXKIBJD-QURGRASLSA-N n,n-diphenyl-6-[(e)-2-[4-(n-phenylanilino)phenyl]ethenyl]naphthalen-2-amine Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1/C=C/C(C=C1C=C2)=CC=C1C=C2N(C=1C=CC=CC=1)C1=CC=CC=C1 NJWJVPXCXKIBJD-QURGRASLSA-N 0.000 description 1
- CLTPAQDLCMKBIS-UHFFFAOYSA-N n-[4-[4-(dinaphthalen-1-ylamino)phenyl]phenyl]-n-naphthalen-1-ylnaphthalen-1-amine Chemical compound C1=CC=C2C(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 CLTPAQDLCMKBIS-UHFFFAOYSA-N 0.000 description 1
- QKCGXXHCELUCKW-UHFFFAOYSA-N n-[4-[4-(dinaphthalen-2-ylamino)phenyl]phenyl]-n-naphthalen-2-ylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C=C4C=CC=CC4=CC=3)C=3C=C4C=CC=CC4=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=C21 QKCGXXHCELUCKW-UHFFFAOYSA-N 0.000 description 1
- BLFVVZKSHYCRDR-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-2-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-2-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 BLFVVZKSHYCRDR-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 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
- RYZPDEZIQWOVPJ-UHFFFAOYSA-N n-naphthalen-1-yl-n-[4-[4-[naphthalen-1-yl(naphthalen-2-yl)amino]phenyl]phenyl]naphthalen-2-amine Chemical compound C1=CC=C2C(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C=C4C=CC=CC4=CC=3)C=3C4=CC=CC=C4C=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=CC2=C1 RYZPDEZIQWOVPJ-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
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-O phenylphosphanium Chemical compound [PH3+]C1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-O 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
- 238000005507 spraying Methods 0.000 description 1
- 238000010025 steaming Methods 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
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
- 229910052726 zirconium Inorganic materials 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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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
- 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
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
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- 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
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- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
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- 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
- H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
Abstract
本發明之課題在於提供一種電荷輸送性塗漆,其係包含形成吲哚並咔唑環之2個氮原子雙方皆未被取代之吲哚並咔唑衍生物作為電荷輸送性物質。
其解決手段為一種電荷輸送性塗漆,其係包含由下述式(1)所表示之吲哚並咔唑所構成之電荷輸送性物質、摻質物質、及有機溶劑。
Description
本發明係關於電荷輸送性塗漆、電荷輸送性薄膜及其之製造方法、以及有機電致發光元件及其之製造方法者。
過往,作為發光裝置之一,已知有如有機電致發光(以下,稱為有機EL)元件。有機EL元件一般係具有包含陽極及陰極、配置於該陽極及該陰極間之電荷注入層(電洞注入層或電子注入層)及發光層之多層構造,且藉由使被注入之電子及電洞在發光層進行再結合而發光。
此種發光層或電荷注入層中係使用由有機化合物所構成之電荷輸送性薄膜。於此之中,配置於陽極及發光層間之電洞注入層係負責交換與陽極或發光層之電荷,達成實現有機EL元件之低電壓驅動及高亮度所需要之重要機能。因此,以提升有機EL元件之特性為目的,已有呈現各種探討關於有機EL元件用之電荷輸送性薄膜
形成用材料的狀況。
在此,電荷輸送性薄膜之形成方法可大致區分為由真空蒸鍍法所代表之乾式製程,與由旋轉塗佈法所代表之濕式製程。若比較兩者時,濕式製程具有能有效率地容易製造大面積且高平坦性之薄膜的優點。
基於以上之情事,例如,已提案出包含形成吲哚並咔唑環之2個氮原子並未被伸芳基或雜伸芳基所取代之構造者(例如參照專利文獻1)。又,已提案出包含形成吲哚並咔唑環之2個氮原子被聚合性基所取代之構造者(例如參照專利文獻2)。更進一步,已提出包含形成吲哚並咔唑環之2個氮原子經由鍵結處而鍵結於主鏈上之構造者(例如參照專利文獻3)。又,亦有揭示吲哚並咔唑化合物之合成(例如參照非專利文獻1)。
[專利文獻1]國際公開第2013/002053號公報
[專利文獻2]國際公開第2012/132501號公報
[專利文獻3]國際公開第2012/132556號公報
[非專利文獻1]Organic & Biomolecular Chemistry, 2008年, 66卷, 1738~1742頁
然而,至今為止雖有提出關於使用形成吲哚並咔唑環之2個氮原子被芳基等所取代之吲哚並咔唑衍生物當作電荷輸送性物質之濕式製程用材料之例(例如專利文獻1~3),但尚未發現關於將2個氮原子雙方皆未被取代之吲哚並咔唑衍生物使用作為濕式製程用材料之例。尚且,非專利文獻1中僅有在合成吲哚並咔唑化合物之觀點下之記述,而並無記載或教示關於將取得之吲哚並咔唑化合物使用作為例如有機EL元件中之電荷輸送性薄膜(電洞注入層或電洞輸送層等)。
本發明係有鑑於此等情事所完成者,其目的在於提供一種包含形成吲哚並咔唑環之2個氮原子雙方皆未被取代之吲哚並咔唑衍生物作為電荷輸送性物質之電荷輸送性塗漆、由該塗漆所得之電荷輸送性薄膜及其製造方法、以及具有該薄膜之有機EL元件及其之製造方法。
解決上述課題之本發明態樣之電荷輸送性塗漆,其特徵為包含由下述式(1)所表示之吲哚並咔唑所構成之電荷輸送性物質、摻質物質、及有機溶劑;
(式中、Ar1及Ar2係互相獨立表示可經Z1取代之碳數6~20之芳基、或可經Z1取代之碳數2~20之雜芳基。R1及R2係互相獨立表示鹵素原子、硝基、氰基、胺基、二甲基胺基、羥基、碳數1~20之烷氧基、可經Z2取代之碳數1~20之烷基、可經Z2取代之碳數2~20之烯基、或可經Z2取代之碳數2~20之炔基。Z1表示鹵素原子、硝基、氰基、胺基、二甲基胺基、羥基、碳數1~20之烷氧基、可經Z2取代之碳數1~20之烷基、可經Z2取代之碳數2~20之烯基、或可經Z2取代之碳數2~20之炔基。Z2表示鹵素原子、硝基、氰基、胺基、二甲基胺基、羥基或碳數1~20之烷氧基。n及m表示R1及R2之數,且互相獨立為0~4之整數。)
在此,前述摻質物質係以包含芳基磺酸化合物及雜多酸化合物之至少一者為佳。
解決上述課題之本發明其他態樣之電荷輸送性薄膜,其特徵係由如上述任一記載之電荷輸送性塗漆所構成。
解決上述課題之發明之另外其他態樣之電荷輸送性薄膜之製造方法,其特徵為具有:將上述任一記載之電荷輸送性塗漆塗佈於基材上之步驟,與使有機溶劑蒸
發之步驟。
解決上述課題之本發明之另外其他態樣之有機電致發光元件,其特徵為具備如上述記載之電荷輸送性薄膜。
在此,前述電荷輸送性薄膜係以作為電洞注入層及電洞輸送層之至少一者為佳。
解決上述課題之本發明之另外其他態樣之有機電致發光元件之製造方法,其特徵為使用如上述記載之電荷輸送性薄膜。
本發明之電荷輸送性塗漆,其係包含由形成吲哚並咔唑環之2個氮原子雙方皆未被取代之吲哚並咔唑衍生物所構成之電荷輸送性物質,與摻質物質。因此,使用該塗漆,即能製造電荷輸送性優異之薄膜。且,依據本發明之電荷輸送性塗漆,即使在使用旋轉塗佈法或狹縫塗佈法等之能大面積成膜之各種濕式製程時,仍能適宜製造電荷輸送性優異之薄膜。故,本發明之電荷輸送性塗漆亦係能充足對應近年來在有機EL元件領域中之進展者。
1‧‧‧低分子系有機EL元件(OLED元件)
10‧‧‧玻璃基板
11‧‧‧ITO
12‧‧‧ITO基板(陽極)
13‧‧‧電洞注入層(電荷輸送性薄膜)
14‧‧‧電洞輸送層
15‧‧‧發光層
16‧‧‧電子注入層
17‧‧‧鋁薄膜(陰極)
[圖1]用以說明具有本實施形態之電荷輸送性薄膜之OLED元件之圖。
[圖2]用以說明具有本實施形態之電荷輸送性薄膜之OLED元件之圖。
以下,具體說明關於本發明之實施形態。該實施形態係展示本發明之其一態樣者,在本發明之範圍內皆能任意地變更。尚且,本說明書中之電荷輸送性係與導電性為同義,亦係與電洞輸送性為同義。電荷輸送性物質可為其自身具有電荷輸送性者,亦可為在與摻質物質(電子受容性物質)一同時進而發揮電荷輸送性者。又,電荷輸送性塗漆可為其自身具有電荷輸送性者,亦可為藉此而得之固態膜為具有電荷輸送性者。
本實施形態之電荷輸送性塗漆為包含下述式(1)所表示之電荷輸送性物質、摻質物質及有機溶劑者。即,本實施形態之電荷輸送性塗漆係使作為主要擔當電荷輸送機能之主材料之該電荷輸送性物質,與該摻質物質一同地在濕式製程中能使用之程度下溶解於該有機溶劑而成者。其中,電荷輸送性物質係由其之2個氮原子雙方皆未被取代之吲哚並咔唑衍生物所構成。藉由使用由此種吲哚並咔唑衍生物所構成之電荷輸送性物質之濕式製程,而形成之稱為有機EL元件之電洞注入層即電荷輸送性薄膜之例,則為新穎者。
上述式(1)中,Ar1及Ar2係互相獨立為可經Z1取代之碳數6~20之芳基、或可經Z1取代之碳數2~20之雜芳基。R1及R2係互相獨立表示鹵素原子、硝基、氰基、胺基、二甲基胺基、羥基、碳數1~20之烷氧基、可經Z2取代之碳數1~20之烷基、可經Z2取代之碳數2~20之烯基、或可經Z2取代之碳數2~20之炔基。Z1表示鹵素原子、硝基、氰基、胺基、二甲基胺基、羥基、碳數1~20之烷氧基、可經Z2取代之碳數1~20之烷基、可經Z2取代之碳數2~20之烯基、或可經Z2取代之碳數2~20之炔基。Z2表示鹵素原子、硝基、氰基、胺基、二甲基胺基、羥基或碳數1~20之烷氧基。n及m表示R1及R2之數,且互相獨立為0~4之整數。
其中作為碳數6~20之芳基,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、4-聯苯基及4-三聯苯基等。
又,作為碳數2~20之雜芳基,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。
又,作為鹵素原子,可舉出如氟原子、氯原子、溴原子、碘原子等。又,作為碳數1~20之烷氧基,可舉出如甲氧基、乙氧基、n-丙氧基、異丙氧基、n-丁氧基、異丁氧基、s-丁氧基、t-丁氧基、n-戊基、n-己氧基、n-庚氧基、n-辛氧基、n-壬氧基、n-癸氧基等。
又,作為碳數1~20之烷基,可為直鏈狀、分枝鏈狀、環狀之任意者,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之直鏈或分枝鏈狀烷基;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之環狀烷基等。
又,作為碳數2~20之烯基,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-1-二十烯基等。
又,作為碳數2~20之炔基,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-1-十五炔基、n-1-二十炔基等。
根據此種電荷輸送性物質,即便係使其一同與摻質物質溶解於有機溶劑而使用於能大面積地成膜之各種濕式製程時,仍可成為能適宜製造電荷輸送性優異之電荷輸送性薄膜之電荷輸送性塗漆。
在此,作為本實施形態所使用之電荷輸送性物質之較佳態樣之一,可舉出能實現對有機溶劑之溶解性或電荷輸送性塗漆之低分子量性者。藉此,而能提供塗佈後容易擴散之電荷輸送性塗漆,且藉由例如由旋轉塗佈法所代表之濕式製程,而變得能將大面積且高平坦性之電荷輸送性薄膜有效率地製造成如ITO或IZO等之透明電極。
因此,上述式(1)中,n及m之至少一者係以0為佳,n及m之兩者皆係0為較佳。作為上述式(1),例如可使用下述式(2)所表示者。
另一方面,從提升電荷輸送性物質對有機溶劑之溶解性之觀點,上述式(1)及(2)之Ar1及Ar2之
至少一者係以芳基為佳,並且以Ar1及Ar2皆為芳基為較佳。又,在上述式(1)中之Ar1及Ar2之至少一者為經Z1取代者時,從提升取得之薄膜之電荷輸送性之觀點,該Z1係以鹵素原子為佳,以氟為較佳。
故,作為本實施形態所使用之電荷輸送性物質之態樣,例如可舉出如下述式(a-1)~(a-21)所表示者。藉由使用使此等電荷輸送性物質如上述般地與摻質物質一同地溶解於有機溶劑所製造之電荷輸送性塗漆,即能製造電荷輸送性優異之電荷輸送性薄膜。此等電荷輸送性物質為低分子量,且對於有機溶劑之溶解性亦優異。因此,使用該電荷輸送性塗漆,藉由濕式製程,即能有效率地製造大面積且高平坦性之電荷輸送性薄膜。
尚且,本實施形態之電荷輸送性物質係能利用非專利文獻1記載之方法,即利用下述反應流程而進行合成。
上述反應流程中,式(3)~(5)所表示之化合物之添加比(式(3):式(4)及(5))係能以1:2程度為基準而適宜調節。式(3)~(5)所表示之化合物係能藉由常法而得取,但即便使用市售品亦無妨。
以上說明之本實施形態所使用之電荷輸送性物質在考慮到對有機溶劑之溶解性等時,其分子量係以2,000以下為佳,較佳為1,000以下。又本實施形態中,電荷輸送性物質係可單獨使用1種單獨,亦可併用2種以上。
並且,在不變更本發明之要旨範圍內,亦可併用其他電荷輸送性物質。作為其他電荷輸送性物質,可舉出例如特開2002-151272號公報記載之寡苯胺衍生物、
國際公開第2004/105446號公報記載之寡苯胺化合物、國際公開第2005/043962號公報記載之具有1,4-二噻英(dithiin)環之化合物、國際公開第2008/032617號公報記載之寡苯胺化合物、國際公開第2008/032616號公報記載之寡苯胺化合物、國際公開第2013/042623號公報記載之芳基二胺化合物等。
尤其,作為其他電荷輸送性物質,以分子量為200~4,000程度之苯胺衍生物為佳。
其次,說明關於本實施形態之電荷輸送性塗漆所使用之摻質物質。作為摻質物質,只要係能溶解於電荷輸送性塗漆所含之有機溶劑中者,則無特別限定,即能適宜選擇使用。若從提升取得之電荷輸送性薄膜之穿透率之觀點評鑑,摻質物質係以芳基磺酸化合物為佳,在考量到對有機溶劑之溶解性時,其分子量係以3,000以下為佳,較佳為2,000以下,更較佳為1,000以下。作為能適宜使用當作摻質物質之芳基磺酸化合物,可舉出例如,下述式(6)或式(7)所表示者。
A1表示O或S,但以O為佳。
A2表示萘環或蒽環,但以萘環為佳。
A3表示2~4價之全氟聯苯基,l表示A1與A3之結合數且為滿足2≦l≦4之整數,但以A3為2價之全氟聯苯基且l係2為佳。
j表示鍵結於A2之磺酸基數且係滿足1≦j≦4之整數,但以2為最佳。
A4~A8係互相獨立表示氫原子、鹵素原子、氰基、碳數1~20之烷基、碳數1~20之鹵化烷基、或碳數2~20之鹵化烯基,但A4~A8之中至少3個為鹵素原子。
作為碳數1~20之鹵化烷基,可舉出如上述碳數1~20之烷基之氫原子之至少一個經鹵素原子所取代者。作為具體例,可舉出如三氟甲基、2,2,2-三氟乙基、1,1,2,2,2-五氟乙基、3,3,3-三氟丙基、2,2,3,3,3-五氟丙基、1,1,2,2,3,3,3-七氟丙基、4,4,4-三氟丁基、3,3,4,4,4-五氟丁基、2,2,3,3,4,4,4-七氟丁基、1,1,2,2,3,3,4,4,4-九氟丁基等。
作為碳數2~20之鹵化烯基,可舉出如上述碳數2~20之烯基之氫原子之至少一個經鹵素原子所取代者。作為具體例,可舉出如全氟乙烯基、全氟丙烯基(烯丙基)、全氟丁烯基等。其他,作為鹵素原子、碳數1~20之烷基之例,可舉出與上述相同者,但鹵素原子係以氟原子為佳。
此等之中,亦以A4~A8為氫原子、鹵素原子、氰基、碳數1~10之烷基、碳數1~10之鹵化烷基、或
碳數2~10之鹵化烯基,且A4~A8之中至少3個係氟原子為佳,又以氫原子、氟原子、氰基、碳數1~5之烷基、碳數1~5之氟化烷基、或碳數2~5之氟化烯基,且A4~A8之中至少3個係氟原子為較佳,另以氫原子、氟原子、氰基、碳數1~5之全氟烷基、或碳數1~5之全氟烯基,且A4、A5及A8係氟原子為更較佳。尚且,全氟烷基係指烷基之氫原子全部被氟原子取代之基,全氟烯基係指烯基之氫原子全部被氟原子取代之基。
k表示鍵結於萘環之磺酸基數且係滿足1≦k≦4之整數,但以2~4為佳,以2為最佳。作為摻質物質所適宜之芳基磺酸化合物之具體例,例如如以下所示。
但,摻質物質並非受限於上述式(b-1)~(b-6),與上述芳基磺酸化合物一同地,或取代上述芳基磺酸化合物而使用具有其他構造之芳基磺酸化合物亦可。更進一步,與上述芳基磺酸化合物一同地,或取代上述芳基磺酸化合物而使用芳基磺酸化合物以外之摻質物質(其他摻質物質)亦可。
作為此種其他摻質物質之適宜者之一例,可舉出如雜多酸化合物。藉由使用雜多酸化合物作為摻質物質,即能取得不僅展現來自以銦錫氧化物(ITO)、銦鋅氧化物(IZO)所代表之透明電極之高電洞收容能力,且展現來自以鋁所代表之金屬陽極之高電洞收容能力之在電荷輸送性上優異之電荷輸送性薄膜(電洞注入層或電洞輸送層等)。
雜多酸化合物係指代表性地以式(C1)所示之Keggin型或式(C2)所示之Dawson型之化學構造所示之具有雜原子位於分子中心之構造,且、釩(V)、鉬(Mo)、鎢(W)等之氧酸即同素聚合酸,與異種元素之氧酸進行縮合而成之多元酸。作為此種異種元素之氧酸,主要可舉出如矽(Si)、磷(P)、砷(As)之氧酸。
作為雜多酸化合物之具體例,可舉出如磷鉬酸、矽鉬酸、磷鎢酸、矽鎢酸、磷鎢鉬酸等,此等係可單獨使用,亦可併用2種以上。尚且,本實施形態中能使用之雜多酸化合物係能作為市售品取得,又亦能藉由公知之方法進行合成。
尤其,摻質物質係單獨由1種類之雜多酸化
合物所構成時,該1種類之雜多酸化合物係以磷鎢酸或磷鉬酸為佳,但以磷鎢酸為適宜。又,摻質物質係由2種類以上之雜多酸化合物所構成時,該2種類以上之雜多酸化合物之一係以磷鎢酸或磷鉬酸為佳,但以磷鎢酸為較佳。尚且,雜多酸化合物在元素分析等之定量分析下,即使係元素之數量多於或少於一般式所示之構造者,其只要係取得作為市售品或藉由公知之合成方法適宜合成者,皆能使用在本實施形態中。
本實施形態中能使用之摻質物質並不受限於前述之例,在不變更本發明之要旨範圍內,則能使用具電子收容性之其他摻質物質。本實施形態之電荷輸送性塗漆所包含之摻質物質,以質量比計,相對於電荷輸送性物質1而言,可作成1.0~70.0程度,較佳為2.0~60.0程度,更佳為2.5~55.0程度,較更佳為2.5~30.0程度,再更佳為2.5~20.0程度,較再更佳為2.5~10.0程度。又本實施形態之電荷輸送性塗漆所包含之摻質物質並非係受限於1種類者,亦可併用2種以上之摻質物質。
其次,說明關於本實施形態之電荷輸送性塗漆所包含之有機溶劑。作為在調製電荷輸送性塗漆時所使用之有機溶劑,在電荷輸送性塗漆成為在濕式製程中能使用之程度下,可使用能良好地溶解電荷輸送性物質及摻質物質之高溶解性溶劑(良溶劑)。作為此種高溶解性溶劑,例如可使用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-咪唑啉酮、二乙二醇
單甲基醚、丙二醇單甲基醚等之有機溶劑。此等溶劑係可單獨使用1種,或能將2種以上混合使用,其使用量在相對於塗漆所使用之溶劑全體而言,可設成5~100質量%。
尚且,本實施形態中能使用之有機溶劑並非係限定在前述之例,亦能與上述高溶解性溶劑一同地使用,或能取代上述高溶解性溶劑而使用比高溶解性溶劑還低極性之低極性溶劑(貧溶劑)。藉由使用低極性溶劑,溶劑分子之極性為低,在對於高極性化合物之溶解性之面下雖較差,但根據溶劑之種類,藉由提升黏度、降低表面張力、賦予揮發性等,而能謀求提升對基板之塗覆性,又,具有能賦予適宜於各種塗佈裝置之噴霧或塗佈之物性,降低對於塗佈裝置之腐蝕性的情況。
又,本實施形態中,藉由使塗漆含有至少一種在25℃下具有10~200mPa‧s,尤其係具有35~150mPa‧s之黏度,且常壓(大氣壓)下沸點為50~300℃,尤其係150~250℃之高黏度有機溶劑,而變得容易調整塗漆之黏度,其結果係變得能再現性良好地賦予高平坦性之電荷輸送性薄膜般之因應所使用之塗佈方法進行調整塗漆。高黏度有機溶劑對本實施形態所用之溶劑全體之添加比例,以在不使固體析出之範圍內為佳,只要不使固體析出,其添加比例係以5~80質量%為佳。並且,以提升對基板之濡潤性、調整溶劑表面張力、調整極性、調整沸點等為目的,相對於塗漆所使用之溶劑全體,亦能在1~90質量%,較佳為1~50質量%之比例下混合其他溶劑。
本實施形態之塗漆之黏度係能因應製作之電荷輸送性薄膜之厚度等或固體成分濃度而適宜設定者,通常在25℃下為1~50mPa‧s。又,本實施形態中之電荷輸送性塗漆之固體成分濃度係在考慮到塗漆黏度及表面張力等,或所製作之電荷輸送性薄膜之厚度等而適宜設定者,但通常為0.1~10.0質量%程度,若考慮到提升塗漆塗佈性時,則以0.5~5.0質量%為佳,較佳為1.0~3.0質量%。
將以上所說明之電荷輸送性塗漆塗佈於基材上進行燒成,即能在基材上形成電荷輸送性薄膜。塗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、刷毛塗佈法、噴墨法、噴霧法等,又以因應塗佈方法而調節塗漆之黏度及表面張力為佳。
又,在使用本實施形態之電荷輸送性塗漆時,燒成環境係通常為大氣環境。燒成溫度在考慮到取得之電荷輸送性薄膜之用途、賦予取得之電荷輸送性薄膜之電荷輸送性程度等,則大約在100~260℃之範圍內適宜設定者,但在將取得之電荷輸送性薄膜使用作為有機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,在燒成之際,在以使其展現較高均勻成膜性,或在基材上使反應進行為目的,亦可提供2段階以上之溫度變化,而加熱係例如使用加熱板或烤箱等適宜機器進行即可。
電荷輸送性薄膜之膜厚雖並無特別限定,但
在有機EL元件內使用作為電洞注入層時,則以5~200nm為佳。作為使膜厚變化之方法,則有使塗漆中之固體成分濃度變化,或使塗佈時基板上之溶液量變化等之方法。
作為在製作使用本實施形態之電荷輸送性塗漆之低分子系有機EL元件(以下,稱為OLED元件)時之使用材料,或製作方法,可舉出如以下所述般者,但並非係限定於此等。所使用之電極基板係以預先藉由洗淨劑、醇、純水等進行液體洗淨而受到淨化者為佳,例如,陽極基板係在使用前先進行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。
圖1係展示具有本實施形態之電荷輸送性薄膜(例如電洞注入層)之OLED元件之構成例的剖面圖。本實施形態之OLED元件1之一例,係能於玻璃基板10之表面上依序層合ITO11經圖型化之ITO基板12(陽極)、電洞注入層13、電洞輸送層14、發光層15、電子注入層16及鋁薄膜17(陰極)而構成者。但,在不縮限本發明之要旨範圍內,亦可追加其他之層。
該OLED元件1之製作方法之例係如以下所述。在成為陽極之ITO基板12上,塗佈本實施形態之電荷輸送性塗漆並進行燒成,而在此ITO基板12上製成電洞注入層13。將此導入於真空蒸鍍裝置內,依序蒸鍍電洞輸送層14、發光層15、因應必要所設置之電子輸送層/電洞阻隔層(未圖示)、電子注入層16、成為陰極之
例如鋁薄膜17而製成OLED元件1。尚且,因應必要在發光層15與電洞輸送層14之間亦可設置電子阻隔層。
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,或由鋁所代表之金屬或由此等合金等所構成之金屬陽極,亦以已實施平坦化處理者為佳。亦能使用具有高電荷輸送性之聚噻吩衍生物或聚苯胺衍生物。
尚且,作為構成金屬陽極之其他金屬,可舉出例如,鈧、鈦、釩、鉻、錳、鐵、鈷、鎳、銅、鋅、鎵、釔、鋯、鈮、鉬、釕、銠、鈀、鎘、銦、鈧、鑭、鈰、鐠、釹、鉅、釤、銪、釓、鋱、鏑、鈥、鉺、銩、鐿、鉿、鉈、鎢、錸、鋨、銥、鉑、金、鈦、鉛、鉍或此等之合金等。
作為形成電洞輸送層14之材料,可舉出如(三苯基胺)二聚物衍生物、[(三苯基胺)二聚物]螺二聚物、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-聯苯胺(α-NPD)、N,N’-雙(萘-2-基)-N,N’-雙(苯基)-聯苯胺、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-聯苯胺、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-9,9-旋環雙茀、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-9,9-旋環雙茀、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-9,9-二甲基-茀、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-9,9-二甲基-茀、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-9,9-二苯基-茀、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-9,9-二苯基-茀、N,N’-雙
(萘-1-基)-N,N’-雙(苯基)-2,2’-二甲基聯苯胺、2,2’,7,7’-肆(N,N-二苯基胺基)-9,9-旋環雙茀、9,9-雙[4-(N,N-雙-聯苯基-4-基-胺基)苯基]-9H-茀、9,9-雙[4-(N,N-雙-萘-2-基-胺基)苯基]-9H-茀、9,9-雙[4-(N-萘-1-基-N-苯基胺基)-苯基]-9H-茀、2,2’,7,7’-肆[N-萘基(苯基)-胺基]-9,9-旋環雙茀、N,N’-雙(菲-9-基)-N,N’-雙(苯基)-聯苯胺、2,2’-雙[N,N-雙(聯苯基-4-基)胺基]-9,9-旋環雙茀、2,2’-雙(N,N-二苯基胺基)-9,9-旋環雙茀、二-[4-(N,N-二(p-甲苯基)胺基)-苯基]環己烷、2,2’,7,7’-四(N,N-二(p-甲苯基))胺基-9,9-旋環雙茀、N,N,N’,N’-四-萘-2-基-聯苯胺、N,N,N’,N’-四-(3-甲基苯基)-3,3’-二甲基聯苯胺、N,N’-二(萘基)-N,N’-二(萘-2-基)-聯苯胺、N,N,N’,N’-四(萘基)-聯苯胺、N,N’-二(萘-2-基)-N,N’-二苯基聯苯胺-1,4-二胺、N1,N4-二苯基-N1,N4-二(m-甲苯基)苯-1,4-二胺、N2,N2,N6,N6-四苯基萘-2,6-二胺、參(4-(喹啉-8-基)苯基)胺、2,2’-雙(3-(N,N-二(p-甲苯基)胺基)苯基)聯苯、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)等之三芳基胺類、5,5”-雙-{4-[雙(4-甲基苯基)胺基]苯基}-2,2’:5’,2”-三噻吩(BMA-3T)等之寡噻吩類等。
作為形成發光層15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-苯基苯酚)鋁(III)(BAlq)、4,4’-雙(2,2-二苯基乙烯基)聯苯、9,10-二(萘-2-基)蒽、2-t-丁基-9,10-二(萘-2-基)蒽、2,7-雙[9,9-二(4-甲基苯基)-茀-2-基]-9,9-二(4-甲基苯基)茀、2-甲基-9,10-雙(萘-2-基)蒽、2-(9,9-旋環雙茀-2-基)-9,9-旋環雙茀、2,7-雙(9,9-旋環雙茀-2-基)-9,9-旋環雙茀、2-[9,9-二(4-甲基苯基)-茀-2-基]-9,9-二(4-甲基苯基)茀、2,2’-二芘基-9,9-旋環雙茀、1、3、5-參(芘-1-基)苯、9,9-雙[4-(芘基)苯基]-9H-茀、2,2’-聯(9,10-二苯基蒽)、2,7-二芘基-9,9-旋環雙茀、1,4-二(芘-1-基)苯、1,3-二(芘-1-基)苯、6,13-二(聯苯基-4-基)稠五苯、3,9-二(萘-2-基)苝、3,10-二(萘-2-基)苝、參[4-(芘基)-苯基]胺、10,10’-二(聯苯基-4-基)-9,9’-聯蒽、N,N’-二(萘-1-基)-N,N’-二苯基-[1,1’:4’,1”:4”,1'''-四聯苯基]-4,4'''-二胺、4,4’-二[10-(萘-1-基)蒽-9-基]聯苯、二苯並{[f,f’]-4,4’,7,7’-四苯基}二茚並[1,2,3-cd:1’,2’,3’-lm]苝、1-(7-(9,9’-聯蒽-10-基)-9,9-二甲基-9H-茀-2-基)芘、1-(7-(9,9’-聯蒽-10-基)-9,9-二己基-9H-茀-2-基)芘、1,3-雙(咔唑-9-基)苯)、1,3,5-參(咔唑-9-基)苯、4,4’,4”-參(咔唑-9-基)三苯基胺、4,4’-雙(咔唑-9-基)聯苯、4,4’-雙(咔唑-9-基)-2,2’-二甲基聯苯、2,7-雙(咔唑-9-基)-9,9-二甲基茀、2,2’,7,7’-肆(咔唑-9-基)-9,9-旋環雙茀、2,7-雙(咔唑-9-基)-9,9-二(p-甲苯基)茀、9,9-雙[4-
(咔唑-9-基)-苯基]茀、2,7-雙(咔唑-9-基)-9,9-旋環雙茀、1,4-雙(三苯基矽基)苯、1,3-雙(三苯基矽基)苯、雙(4-N,N-二乙基胺基-2-甲基苯基)-4-甲基苯基甲烷、2,7-雙(咔唑-9-基)-9,9-二辛基茀、4,4”-二(三苯基矽基)-p-三聯苯、4,4’-二(三苯基矽基)聯苯、9-(4-t-丁基苯基)-3,6-雙(三苯基矽基)-9H-咔唑、9-(4-t-丁基苯基)-3,6-貳三苯甲基-9H-咔唑、9-(4-t-丁基苯基)-3,6-雙(9-(4-甲氧基苯基)-9H-茀-9-基)-9H-咔唑、2,6-雙(3-(9H-咔唑-9-基)苯基)吡啶、三苯基(4-(9-苯基-9H-茀-9-基)苯基)矽烷、9,9-二甲基-N,N-二苯基-7-(4-(1-苯基-1H-苯並[d]咪唑-2-基)苯基)-9H-茀-2-胺、3,5-雙(3-(9H-咔唑-9-基)苯基)吡啶、9,9-旋環雙茀-2-基-二苯基-膦氧化物、9,9’-(5-(三苯基矽基)-1,3-伸苯基)雙(9H-咔唑)、3-(2,7-雙(二苯基磷醯基)-9-苯基-9H-茀-9-基)-9-苯基-9H-咔唑、4,4,8,8,12,12-六(p-甲苯基)-4H-8H-12H-12C-氮雜二苯並[cd,mn]芘、4,7-二(9H-咔唑-9-基)-1,10-啡啉、2,2’-雙(4-(咔唑-9-基)苯基)聯苯、2,8-雙(二苯基磷醯基)二苯並[b,d]噻吩、雙(2-甲基苯基)二苯基矽烷、雙[3,5-二(9H-咔唑-9-基)苯基]二苯基矽烷、3,6-雙(咔唑-9-基)-9-(2-乙基-己基)-9H-咔唑、3-(二苯基磷醯基)-9-(4-(二苯基磷醯基)苯基)-9H-咔唑、3,6-雙[(3,5-二苯基)苯基]-9-苯基咔唑等,亦可藉由與發光性摻質進行共蒸鍍,而形成發光層15。
作為發光性摻質,可舉出如3-(2-苯並噻唑基)-7-(二乙基胺基)香豆素、2,3,6,7-四氫-1,1,7,7-四甲基-1H,5H,11H-10-(2-苯並噻唑基)喹嗪基[9,9a,lgh]香豆素、喹吖啶酮、N,N’-二甲基-喹吖啶酮、參(2-苯基吡啶)銥(Ir(ppy)3)、雙(2-苯基吡啶)(乙醯基丙酮酸)銥(Ir(ppy)2(acac))、參[2-(p-甲苯基)吡啶]銥(Ir(mppy)3)、9,10-雙[N,N-二(p-甲苯基)胺基]蒽、9,10-雙[苯基(m-甲苯基)胺基]蒽、雙[2-(2-羥基苯基)苯並噻唑]鋅、N10,N10,N10’,N10’-四(p-甲苯基)-9,9’-聯蒽-10,10’-二胺、N10,N10,N10’,N10’-四苯基-9,9’-聯蒽-10,10’-二胺、N10,N10’-二苯基-N10’,N10’-二萘基-9,9’-聯蒽-10,10’-二胺、4,4’-雙(9-乙基-3-咔唑乙烯基)-1,1’-聯苯、苝、2,5,8,11-四-t-丁基苝、1、4-雙[2-(3-N-乙基咔唑)乙烯基]苯、4,4’-雙[4-(二-p-甲苯基胺基)苯乙烯基]聯苯、4-(二-p-甲苯基胺基)-4’-[(二-p-甲苯基胺基)苯乙烯基]茋、雙(3,5-二氟-2-(2-吡啶基)苯基-(2-羧基吡啶基)銥、4,4’-雙[4-(二苯基胺基)苯乙烯基]聯苯、雙(2,4-二氟苯基吡啶)肆(1-吡唑基)硼酸銥、N,N’-雙(萘-2-基)-N,N’-雙(苯基)-參(9,9-二甲基伸茀基)、2,7-雙{2-[苯基(m-甲苯基)胺基]-9,9-二甲基-茀-7-基}-9,9-二甲基-茀、N-(4-((E)-2-(6((E)-4-(二苯基胺基)苯乙烯基)萘-2-基)乙烯基)苯基)-N-苯基苯胺、fac-銥參(1-苯基-3-甲基苯並咪唑啉-2-亞基-C,C2’)、mer-銥參(1-苯基-3-甲基苯並咪唑啉-2-亞基-C,C2’)、
2,7-雙[4-(二苯基胺基)苯乙烯基]-9,9-旋環雙茀、6-甲基-2-(4-(9-(4-(6-甲基苯並[d]噻唑-2-基)苯基)蒽-10-基)苯基)苯並[d]噻唑、1,4-二[4-(N,N-二苯基)胺基]苯乙烯基苯、1,4-雙(4-(9H-咔唑-9-基)苯乙烯基)苯、(E)-6-(4-(二苯基胺基)苯乙烯基)-N,N-二苯基萘-2-胺、雙(2,4-二氟苯基吡啶)(5-(吡啶-2-基)-1H-四唑基)銥、雙(3-三氟甲基-5-(2-吡啶基)吡唑)((2,4-二氟苄基)二苯基亞膦酸)銥、雙(3-三氟甲基-5-(2-吡啶基)吡唑)(苄基二苯基亞膦酸)銥、雙(1-(2,4-二氟苄基)-3-甲基苯並咪唑)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑)銥、雙(3-三氟甲基-5-(2-吡啶基)吡唑)(4’,6’-二氟苯基吡啶)銥、雙(4’,6’-二氟苯基吡啶)(3,5-雙(三氟甲基)-2-(2’-吡啶基)吡咯)銥、雙(4’,6’-二氟苯基吡啶)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑)銥、(Z)-6-莱基-N-(6-莱基喹啉-2(1H)-亞基)喹啉-2-胺-BF2、(E)-2-(2-(4-(二甲基胺基)苯乙烯基)-6-甲基-4H-哌喃-4-亞基)丙二腈、4-(二氰基亞甲基)-2-甲基-6-久咯啶基-9-烯-4H-哌喃、4-(二氰基亞甲基)-2-甲基-6-(1,1,7,7-四甲基久咯啶基-9-烯)-4H-哌喃、4-(二氫基亞甲基)-2-t-丁基-6-(1,1,7,7-四甲基久咯啶-4-基-乙烯基)-4H-哌喃、參(二苄醯基甲烷)啡啉銪、5,6,11,12-四苯基稠四苯、雙(2-苯並[b]噻吩-2-基-吡啶)(乙醯基丙酮酸)銥、參(1-苯基異喹啉)銥、雙(1-苯基異喹啉)(乙醯基丙酮酸)銥、
雙[1-(9,9-二甲基-9H-茀-2-基)-異喹啉](乙醯基丙酮酸)銥、雙[2-(9,9-二甲基-9H-茀-2-基)喹啉](乙醯基丙酮酸)銥、參[4,4’-二-t-丁基-(2,2’)-聯吡啶]釕雙(六氟磷酸酯)、參(2-苯基喹啉)銥、雙(2-苯基喹啉)(乙醯基丙酮酸)銥、2,8-二-t-丁基-5,11-雙(4-t-丁基苯基)-6,12-二苯基稠四苯、雙(2-苯基苯並噻唑)(乙醯基丙酮酸)銥、5,10,15,20-四苯基四苯並卟啉鉑、鋨雙(3-三氟甲基-5-(2-吡啶)-吡唑)二甲基苯基膦、鋨雙(3-(三氟甲基)-5-(4-t-丁基吡啶基)-1,2,4-三唑)二苯基甲基膦、鋨雙(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑)二甲基苯基膦、鋨雙(3-(三氟甲基)-5-(4-t-丁基吡啶基)-1,2,4-三唑)二甲基苯基膦、雙[2-(4-n-己基苯基)喹啉](乙醯基丙酮酸)銥、參[2-(4-n-己基苯基)喹啉]銥、參[2-苯基-4-甲基喹啉)]銥、雙(2-苯基喹啉)(2-(3-甲基苯基)吡啶)銥、雙(2-(9,9-二乙基-茀-2-基)-1-苯基-1H-苯並[d]咪唑)(乙醯基丙酮酸)銥、雙(2-苯基吡啶)(3-(吡啶-2-基)-2H-苯并哌喃-2-酸)銥、雙(2-苯基喹啉)(2,2,6,6-四甲基庚-3,5-二酸)銥、雙(苯基異喹啉)(2,2,6,6-四甲基庚-3,5-二酸)銥、銥雙(4-苯基噻吩並[3,2-c]吡啶-N,C2’)乙醯基丙酮酸、(E)-2-(2-t-丁基-6-(2-(2,6,6-三甲基-2,4,5,6-四氫-1H-吡咯並[3,2,1-ij]喹啉-8-基)乙烯基)-4H-哌喃-4-亞基)丙二腈、雙(3-三氟甲基-5-(1-異喹啉基)吡唑)(甲基二苯基膦)釕、雙[(4-n-己基苯基)異
喹啉](乙醯基丙酮酸)銥、鉑八乙基卟吩、雙(2-甲基二苯並[f,h]喹喔啉)(乙醯基丙酮酸)銥、參[(4-n-己基苯基)羥基喹啉]銥等。
作為形成電子輸送層/電洞阻隔層之材料,可舉出如8-羥基喹啉-鋰、2,2’,2”-(1,3,5-苯甲苯基)-參(1-苯基-1-H-苯並咪唑)、2-(4-聯苯基)5-(4-t-丁基苯基)-1,3,4-惡二唑、2,9-二甲基-4,7-二苯基-1,10-啡啉、4,7-二苯基-1,10-啡啉、雙(2-甲基-8-喹啉)-4-(苯基苯酚)鋁、1,3-雙[2-(2,2’-聯吡啶-6-基)-1,3,4-噁二唑-5-基]苯、6,6’-雙[5-(聯苯基-4-基)-1,3,4-噁二唑-2-基]-2,2’-聯吡啶、3-(4-聯苯基)-4-苯基-5-t-丁基苯基-1,2,4-三唑、4-(萘-1-基)-3,5-二苯基-4H-1,2,4-三唑、2,9-雙(萘-2-基)-4,7-二苯基-1,10-啡啉、2,7-雙[2-(2,2’-聯吡啶-6-基)-1,3,4-噁二唑-5-基]-9,9-二甲基茀、1,3-雙[2-(4-t-丁基苯基)-1,3,4-噁二唑-5-基]苯、參(2,4,6-三甲基-3-(吡啶-3-基)苯基)硼烷、1-甲基-2-(4-(萘-2-基)苯基)-1H-咪唑並[4,5f][1,10]啡啉、2-(萘-2-基)-4,7-二苯基-1,10-啡啉、苯基-二芘基膦氧化物、3,3’,5,5’-四[(m-吡啶基)-苯-3-基]聯苯、1,3,5-參[(3-吡啶基)-苯-3-基]苯、4,4’-雙(4,6-二苯基-1,3,5-三嗪-2-基)聯苯、1,3-雙[3,5-二(吡啶-3-基)苯基]苯、雙(10-羥基苯並[h]喹啉)鈹、二苯基雙(4-(吡啶-3-基)苯基)矽烷、3,5-二(芘-1-基)吡啶等。
作為形成電子注入層16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)、氟化銫(CsF)、氟化鍶(SrF2)、三氧化鉬(MoO3)、鋁、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。作為行程電子阻隔層之材料,可舉出如參(苯基吡唑)銥等。
如圖2(a)~(b)所示,對OLED元件1之ITO基板12(陽極)及鋁薄膜17(陰極)施加電壓時,在HOMO及LUMO產生內部梯度,電洞從ITO基板12朝向發光層15側注入於HOMO,又,電子從鋁薄膜17朝向發光層15側注入於LUMO。其結果,在發光層15內電洞及電子進行再結合(激發分子從電子輸送材料能量轉移至摻質物質),藉此所發出之光從ITO基板12側朝向OLED元件1外射出。
另外,使用本實施形態之電荷輸送性塗漆而製作高分子系有機EL元件(以下,稱為PLED元件)之方法並無特別限定,可舉出如以下之方法。即,能在上述OLED元件1製作中,取代實施電洞輸送層14、發光層15、電子輸送層(未圖示)、電子注入層16之真空蒸鍍操作,而改為藉由依序形成電洞輸送性高分子層、發光性高分子層,而製成具有由本實施形態之電荷輸送性塗漆所形成之電荷輸送性薄膜的PLED元件。具體而言,在陽極基板上塗佈本實施形態之電荷輸送性塗漆,藉由上述方法
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,更再蒸鍍陰極電極而製成PLED元件。
作為使用之陰極及陽極材料,可使用與在上述OLED元件製作時相同者,且亦能使用相同洗淨處理、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,可舉出如將電洞輸送性高分子材料或發光性高分子材料、或對此等添加摻質物質而成之材料加入於溶劑中使其溶解,或使其均勻分散,並塗佈電洞注入層或電洞輸送性高分子層之上後,分別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[(9,9-二己基茀基-2,7-二基)-共-(N,N’-雙{p-丁基苯基}-1,4-二胺基伸苯基)]、聚[(9,9-二辛基茀基-2,7-二基)-共-(N,N’-雙{p-丁基苯基}-1,1’-伸聯苯基-4,4-二胺)]、聚[(9,9-雙{1’-戊烯-5’-基}茀基-2,7-二基)-共-(N,N’-雙{p-丁基苯基}-1,4-二胺基伸苯基)]、聚[N,N’-雙(4-丁基苯基)-N,N’-雙(苯基)-聯苯胺]-末端封端聚倍半矽氧烷、聚[(9,9-雙二辛基茀基-2,7-二基)-共-(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-苯乙炔)(MEH-PPV)等之聚對苯乙炔衍生物、聚(3-烷基噻吩)(PAT)等之聚噻吩衍生物、聚乙烯咔唑(PVCz)等。
作為溶劑,可舉出如甲苯、茬、氯仿等,且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。作為塗佈方法,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、刷毛塗塗佈等。尚且,塗佈係以在氮、氬等之惰性氣體下進行為佳。作為燒成之方法,可舉出如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而更加詳述本發明,但本發明並非係受下述所限定者。
在此使用之裝置與其使用目的係如下述所示。
基板洗淨:長州產業(股)公司製
基板洗淨裝置(減壓電漿方式)
塗漆之塗佈:三笠(股)公司製
旋轉塗佈器MS-A100
膜厚測量:(股)小坂研究所製
微細形狀測量機Surfcorder ET-4000
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
有機EL元件之製作:長州產業(股)公司製
多機能蒸鍍裝置系統C-E2L1G1-N
有機EL元件之亮度等之測量:(有)Tech World公司製
I-V-L測量系統
依據上述非專利文獻1記載之方法,合成下述式(a-1)所表示之化合物(以下,略稱為A1)及下述式(a-2)所表示之化合物(以下,略稱為A2)。
依序添加吲哚7.00g、二苯基乙二酮(benzil)5.01g、p-甲苯磺酸一水合物0.92g、及甲苯55mL,並以氮氣取代反應系統。其後,在加熱迴流條件下攪拌此溶液8小時。其次,使此溶液冷卻至室溫後,進行過濾。使用管柱層析法純化取得之濾過物,並收集包含目的物之分餾物,餾除溶劑後,施以乾燥。使用1,4-二噁烷120mL對取得之粉末施以再結晶。其後,進行過濾、乾燥,而取得
6,7-二苯基-5,12-二氫吲跺並[3,2-a]咔唑4.95g(收率51%)。
1H NMR(300MHz,THF-d8)δ[ppm]:10.8(s,1H),9.91(s,1H),8.47(d,J=7.7Hz,1H),7.51(d,J=7.7Hz,1H),7.48(d,J=7.7Hz,1H),7.08-7.35(m,13H),6.74-6.80(m,2H)。
依序添加吲哚1.17g、1,2-雙(4-氟苯基)乙-1,2-二酮0.98g、p-甲苯磺酸一水合物0.15g、及甲苯10mL,並以氮氣取代反應系統。其後,在加熱迴流條件下攪拌此溶液7小時。其次,使此溶液冷卻至室溫後,並進行過濾。以甲苯、四氫呋喃及乙醇之混合溶劑將取得之過濾物洗淨後,並施以乾燥,而取得6,7-雙(4-氟苯基)-5,12-二氫吲跺並[3,2-a]咔唑0.46g(收率26%)。
1H NMR(300MHz,DMSO-d6)δ[ppm]:11.9(s,1H),10.8(s,1H),8.72(d,J=7.7Hz,1H),7.64(d,J=8.3Hz,1H),7.57(d,J=8.3Hz,1H),7.11-7.43(m,11H),6.87(t,J=7.7Hz,1H),6.60(d,J=7.7Hz,1H)。
在氮環境下,將0.073g(0.178mmol)之A1及下述
式(b-1)所表示之芳基磺酸化合物(以下,略稱為B1)0.080g(0.089mmol)之混合物添加良溶劑之1,3-二甲基-2-咪唑啉酮(以下,略稱為DMI)2.5g,而使其上述混合物溶解。對此溶液添加環己醇3.75g及丙二醇1.25g,充分進行攪拌後取得黃色透明溶液。使用孔徑0.2μm之PTFE製過濾器過濾取得之黃色透明溶液,而得到黃色透明之電荷輸送性塗漆(固體成分濃度2.0質量%)。尚且,B1係根據國際公開第2006/025342號之記載內容進行合成者。
除了使用0.061g(0.136mmol)之A1及0.092g(0.102mmol)之B1之混合物以外,其他與實施例1-1相同之方法進行實施取得黃色透明之電荷輸送性塗漆(固體成分濃度2.0質量%)。
除了使用0.048g(0.117mmol)之A1及0.105g
(0.117mmol)之A1之混合物以外,其他與實施例1-1相同之方法進行實施而取得黃色透明之電荷輸送性塗漆(固體成分濃度2.0質量%)。
在氮環境下對0.048g(0.117mmol)之A1及0.105g(0.117mmol)之B1之混合物添加DMI 2.5g,而使上述混合物溶解。對此溶液添加環己醇3.75g及丙二醇1.25g,並充分進行攪拌。其後,添加三甲氧基(3,3,3-三氟丙基)矽烷與三(甲氧基苯基)矽烷之1:2(質量比)之混合溶劑0.015g,並充分進行攪拌而取得黃色透明溶液。使用孔徑0.2μm之PTFE製過濾器過濾取得之黃色透明溶液,而得到黃色透明之電荷輸送性塗漆(固體成分濃度2.0質量%)。
除了使用0.046g(0.114mmol)之A1及磷鎢酸(關東化學(股)製)0.186g之混合物以外,其他與實施例1-1相同之方法進行實施而取得黃色透明之電荷輸送性塗漆(固體成分濃度3.0質量%)。
在氮環境下,對0.043g(0.097mmol)之A2及磷鎢酸0.173g之混合物添加DMI 5g,而使上述混合物溶解。
對此溶液添加環己醇1.0g及丙二醇1.0g,並充分進行攪拌而取得黃色透明溶液。使用孔徑0.2μm之PTFE製過濾器過濾取得之黃色透明溶液,而得到黃色透明之電荷輸送性塗漆(固體成分濃度3.0質量%)。
使用旋轉塗佈器將藉由上述方法取得之塗漆([實施例1-1]~[實施例1-6])塗佈於石英基板上後,於大氣中在50℃下乾燥5分鐘,並再230℃下燒成15分鐘,而在石英基板上製成膜厚30nm之均勻薄膜。尚且,石英基板係使用電漿洗淨裝置(150W、30秒鐘),去除表面上雜質後才使用者。
其後,測量所製作之電荷輸送性薄膜([實施例2-1]~[實施例2-6])之穿透率。穿透率係藉由掃描可見光領域即波長400~800nm而得。400~800nm之平均穿透率係如下述表1所示。
從表1之結果,可發現[實施例2-1]~[實施例2-6]之電荷輸送性薄膜再可見領域中展示高穿透率。
藉由下述方法製作圖1所示之OLED元件1。即,使用在25mm×25mm×0.7t之玻璃基板10之表面上ITO11經圖型化成膜厚150nm之ITO基板12作為基板。ITO基板12係使用O2電漿洗淨裝置(150W、30秒鐘)去除表面上雜質後才使用者。
首先,使用旋轉塗佈器,將[實施例1-1]之塗漆塗佈於ITO基板12上後,在50℃下乾燥5分鐘,又在230℃下燒成15分鐘,而在ITO基板12上製成30nm之均勻電荷輸送性薄膜(電洞注入層13)。
在已製成有電荷輸送性薄膜之ITO基板12
上,使用蒸鍍裝置依序形成α-NPD(電洞輸送層14)、Alq3(發光層15)、氟化鋰(LiF;電子注入層16)、及鋁薄膜17,而取得OLED元件1。膜厚係分別作成30nm、40nm、0.5nm及100nm,且在真空度1.0×10-5Pa,蒸鍍速率係LiF為0.02nm/秒,其以外之材料為0.2nm/秒之條件下進行蒸鍍。
尚且,為了防止空氣中之氧、水等之影響所造成之特性劣化,在評價其特性後,以密封基板密封OLED元件1。密封係依據依以下操作順序實施。
在氧濃度5ppm以下、露點-80℃以下之氮環境中,將OLED元件1收納於密封基板之間,藉由接著劑貼合密封基板。此時,將Dynic(股)製HD-071010W-40作為補水劑與OLED元件一同地收納於密封基板內。接著劑係使用(股)MORESCO製Moresco Moisture cut WB90US(P)。對已貼合之密封基板照射UV光(波長:365nm、照射量:6000mJ/cm2)後,在80℃下進行1小時退火處理而使接著劑硬化。
除了使用上述[實施例1-2]~[實施例1-6]中取得之塗漆以外,其他係與[實施例3-1]相同之方法製成OLED元件。
測量關於所製成之OLED元件([實施例3-1]~[實施例3-6])之電流密度及亮度的特性。驅動電壓5V
下之電流密度及亮度係如表2所示。尚且,各元件之發光面尺寸之面積為2mm×2mm。
從表2之結果,發現到[實施例3-1]~[實施例3-6]之OLED元件係在實用性電壓之範圍內具有充分亮度者,即會發光者。從以上之結果,可得知將由本實施形態之電荷輸送性塗漆所得之電荷輸送性薄膜使用作為電洞注入層,即能取得亮度特性優異之有機EL元件。
Claims (7)
- 一種電荷輸送性塗漆,其特徵為包含由下述式(1)所表示之吲哚並咔唑所構成之電荷輸送性物質、摻質物質、及有機溶劑;
- 如請求項1之電荷輸送性塗漆,其中前述摻質物質包含芳基磺酸化合物及雜多酸化合物之至少一者。
- 一種電荷輸送性薄膜,其特徵係由如請求項1或2之電荷輸送性塗漆所構成。
- 一種電荷輸送性薄膜之製造方法,其特徵為具 有:將如請求項1或2之電荷輸送性塗漆塗佈於基材上之步驟,與使有機溶劑蒸發之步驟。
- 一種有機電致發光元件,其特徵為具備如請求項3之電荷輸送性薄膜。
- 如請求項5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及電洞輸送層之至少一者。
- 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3之電荷輸送性薄膜。
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