TWI690532B - 有機電致發光元件用之電荷傳輸性薄膜形成組成物、有機電致發光元件用之電荷傳輸性薄膜及有機電致發光元件 - Google Patents
有機電致發光元件用之電荷傳輸性薄膜形成組成物、有機電致發光元件用之電荷傳輸性薄膜及有機電致發光元件 Download PDFInfo
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- TWI690532B TWI690532B TW105107415A TW105107415A TWI690532B TW I690532 B TWI690532 B TW I690532B TW 105107415 A TW105107415 A TW 105107415A TW 105107415 A TW105107415 A TW 105107415A TW I690532 B TWI690532 B TW I690532B
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- -1 cyano-substituted nitrogen Chemical class 0.000 claims description 189
- 125000004432 carbon atom Chemical group C* 0.000 claims description 124
- 125000005843 halogen group Chemical group 0.000 claims description 71
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- 238000002347 injection Methods 0.000 claims description 59
- 239000007924 injection Substances 0.000 claims description 59
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 42
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 28
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 11
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- 230000005540 biological transmission Effects 0.000 claims description 5
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims description 4
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 3
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- 239000000463 material Substances 0.000 description 28
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- 230000005525 hole transport Effects 0.000 description 16
- 0 Cc1cccc(*c2ccccc2)c1 Chemical compound Cc1cccc(*c2ccccc2)c1 0.000 description 15
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- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 9
- 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 9
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 9
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 8
- 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 8
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- 125000003277 amino group Chemical group 0.000 description 8
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- 238000011282 treatment Methods 0.000 description 8
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 8
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- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 6
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- 229910052782 aluminium Inorganic materials 0.000 description 6
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- 239000003446 ligand Substances 0.000 description 6
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- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 5
- QZHXKQKKEBXYRG-UHFFFAOYSA-N 4-n-(4-aminophenyl)benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NC1=CC=C(N)C=C1 QZHXKQKKEBXYRG-UHFFFAOYSA-N 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- 239000010405 anode material Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-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
- 239000002184 metal Substances 0.000 description 5
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 5
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- 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 4
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- 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 3
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- LHEOFIBQZSRTNC-UHFFFAOYSA-N phenanthrene-3-carbaldehyde Chemical compound C1=CC=C2C3=CC(C=O)=CC=C3C=CC2=C1 LHEOFIBQZSRTNC-UHFFFAOYSA-N 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 235000007686 potassium Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
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- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
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- 238000001226 reprecipitation Methods 0.000 description 1
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- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
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- CGFYHILWFSGVJS-UHFFFAOYSA-N silicic acid;trioxotungsten Chemical compound O[Si](O)(O)O.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 CGFYHILWFSGVJS-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
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- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 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
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- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical compound CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical class N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- GBSZYMVOJYAZPH-UHFFFAOYSA-N thieno[2,3-e][1]benzothiole Chemical class S1C=CC2=C1C=CC1=C2SC=C1 GBSZYMVOJYAZPH-UHFFFAOYSA-N 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical class S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- XVYIJOWQJOQFBG-UHFFFAOYSA-N triethoxy(fluoro)silane Chemical compound CCO[Si](F)(OCC)OCC XVYIJOWQJOQFBG-UHFFFAOYSA-N 0.000 description 1
- SAWDTKLQESXBDN-UHFFFAOYSA-N triethoxy(heptyl)silane Chemical compound CCCCCCC[Si](OCC)(OCC)OCC SAWDTKLQESXBDN-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- FZMJEGJVKFTGMU-UHFFFAOYSA-N triethoxy(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC FZMJEGJVKFTGMU-UHFFFAOYSA-N 0.000 description 1
- FHVAUDREWWXPRW-UHFFFAOYSA-N triethoxy(pentyl)silane Chemical compound CCCCC[Si](OCC)(OCC)OCC FHVAUDREWWXPRW-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- ZRQAIBMAFLMIND-UHFFFAOYSA-N triethoxy(thiophen-2-yl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CS1 ZRQAIBMAFLMIND-UHFFFAOYSA-N 0.000 description 1
- CUVIJHAPWYUQIV-UHFFFAOYSA-N triethoxy-[3-(1,1,1,2,3,3,3-heptafluoropropan-2-yloxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOC(F)(C(F)(F)F)C(F)(F)F CUVIJHAPWYUQIV-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- HILHCDFHSDUYNX-UHFFFAOYSA-N trimethoxy(pentyl)silane Chemical compound CCCCC[Si](OC)(OC)OC HILHCDFHSDUYNX-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- XSVXWCZFSFKRDO-UHFFFAOYSA-N triphenyl-(3-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=C(C=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XSVXWCZFSFKRDO-UHFFFAOYSA-N 0.000 description 1
- DETFWTCLAIIJRZ-UHFFFAOYSA-N triphenyl-(4-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DETFWTCLAIIJRZ-UHFFFAOYSA-N 0.000 description 1
- LNQMQGXHWZCRFZ-UHFFFAOYSA-N triphenyl-[4-(4-triphenylsilylphenyl)phenyl]silane Chemical group C1=CC=CC=C1[Si](C=1C=CC(=CC=1)C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 LNQMQGXHWZCRFZ-UHFFFAOYSA-N 0.000 description 1
- KIGXXTRUJYDDKP-UHFFFAOYSA-N triphenyl-[4-[4-(4-triphenylsilylphenyl)phenyl]phenyl]silane Chemical group C1=CC=CC=C1[Si](C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 KIGXXTRUJYDDKP-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 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
- 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
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- 229910052726 zirconium Inorganic materials 0.000 description 1
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Abstract
本發明提供一種有機電致發光元件用之電荷傳輸性薄膜形成組成物,其特徵為含有由式(D1)~(D5)之任一者表示之經氰基取代的含氮雜芳香族化合物所成之摻雜物物質、電荷傳輸性物質、與有機溶劑,且前述摻雜物物質及前述電荷傳輸性物質係溶解於前述有機溶劑。
Description
本發明係關於有機電致發光元件用之電荷傳輸性薄膜形成組成物、有機電致發光元件用之電荷傳輸性薄膜及有機電致發光元件。
有機電致發光(以下稱為有機EL)元件中,係使用由有機化合物所成之電荷傳輸性膜,作為發光層或電荷注入層。特別是電洞注入層,負責陽極、與電洞傳輸層或發光層之電荷授受,為了達成有機EL元件之低電壓驅動及高輝度,發揮重要的功能。
電洞注入層之形成方法,係粗分為以蒸鍍法為代表之乾式製程、與以旋轉塗佈法為代表之濕式製程,比較此等各製程時,濕式製程較可有效率地製造大面積且平坦性高之薄膜。因此,有機EL顯示器之大面積化有所進展的現在,期望能夠以濕式製程形成的電洞注入層。
有鑑於如此之實情,本發明者等人、係有開發賦予可
應用於各種濕式製程,而且應用於有機EL元件之電洞注入層時可實現優良之EL元件特性的薄膜之電荷傳輸性材料、或對使用於其之有機溶劑的溶解性良好之化合物(例如參照專利文獻1~4)。
但是,伴隨於有機EL領域之進展,經常要求可實現優良EL特性之新穎塗佈型有機EL用材料。
[專利文獻1]國際公開第2008/032616號
[專利文獻2]國際公開第2008/129947號
[專利文獻3]國際公開第2006/025342號
[專利文獻4]國際公開第2010/058777號
[專利文獻5]日本特開2009-079131號公報
[專利文獻6]日本特開2001-341239號公報
[專利文獻7]日本特開2004-189674號公報
[專利文獻8]日本特開平11-222263號公報
本發明係有鑑於上述實情而為者,其目的為提供用以形成應用於有機EL元件時,可實現優良輝度特性之電荷傳輸性薄膜的組成物。
本發明者等人重複努力探討的結果,發現由含有由特定之經氰基取代的含氮雜芳香族(heteroaromatic)化合物所成之摻雜物物質、電荷傳輸性物質、與有機溶劑的組成物,可得到使用作為有機電致發光元件之電洞注入層等的功能層時可實現優良輝度特性之電荷傳輸性薄膜,完成了本發明。
再者,專利文獻5~8中,雖揭示含有2,4,6,7-四氰基-1,4,5,8-四氮雜萘之材料,作為摻雜物(電子接受體),但此等各文獻中,但並無教示如本發明之組成物的有機EL元件用材料之記載、亦無暗示其之記載。
亦即,本發明提供1. 一種有機電致發光元件用之電荷傳輸性薄膜形成組成物,其特徵為含有由式(D1)~(D5)之任一者表示之經氰基取代的含氮雜芳香族化合物所成之摻雜物物質、電荷傳輸性物質、與有機溶劑,且前述摻雜物物質及前述電荷傳輸性物質係溶解於前述有機溶劑,
2. 如1之有機電致發光元件用之電荷傳輸性薄膜形成組成物,其中前述電荷傳輸性物質,為分子量200~9,500之電荷傳輸性化合物;3. 如2之有機電致發光元件用之電荷傳輸性薄膜形成組成物,其中前述電荷傳輸性化合物,為苯胺衍生物或噻吩衍生物;4. 如3之有機電致發光元件用之電荷傳輸性薄膜形成組成物,其中前述電荷傳輸性化合物,為苯胺衍生物;5. 如1~4中任一項之有機電致發光元件用之電荷傳輸性薄膜形成組成物,其中進一步含有有機矽烷化合物;6. 如1~5中任一項之有機電致發光元件用之電荷傳輸性薄膜形成組成物,其中進一步含有雜多酸;7. 如1~6中任一項之有機電致發光元件用之電荷傳輸性薄膜形成組成物,其係有機電致發光元件之電洞注入層、電洞傳輸層或電洞注入傳輸層形成用組成物;8. 一種有機電致發光元件用之電荷傳輸性薄膜,其係使用如1~7中任一項之有機電致發光元件用之電荷傳輸性薄膜形成組成物所製造;9. 一種有機電致發光元件,其係具有如8之有機電致發光元件用之電荷傳輸性薄膜。
藉由使用本發明之組成物,可得到兼具優良平坦性與優良電荷傳輸性,且使用作為有機電致發光元件
之電洞注入層等的功能層時,可實現優良輝度特性之電荷傳輸性薄膜。
該理由雖無定論,但推測係因如2,4,6,7-四氰基-1,4,5,8-四氮雜萘之氰基鍵結於含氮雜芳香環之構造的化合物,不僅含氮雜芳香環中之電子缺損的影響,且藉由其所鍵結之氰基的電子吸引之效果,被期待作為摻雜物而發揮優良功能,因而藉由使用含有電荷傳輸性物質、特別是苯胺衍生物,以及作為摻雜物物質的如此之化合物的本發明之組成物,可得到不僅平坦性及電荷傳輸性優良,且來自陽極之電洞接受能力及對電洞傳輸層或發光層之電洞注入能力亦優良的電荷傳輸性薄膜,結果可得到優良輝度特性之有機EL元件。
又,本發明之組成物,即使使用旋轉塗佈法或狹縫塗佈法等可大面積成膜之各種濕式製程時,亦可再現性良好地製造電荷傳輸性優良的薄膜,因此亦可充分對應於近年來有機EL元件領域中之進展。
以下更詳細說明本發明。
本發明之有機電致發光元件用之電荷傳輸性薄膜形成組成物(以下亦僅稱為本發明之組成物),含有由式(D1)~(D5)之任一者表示之經氰基取代的含氮雜芳香族化合物所成之摻雜物物質。
此等之中,考慮到所得薄膜之電荷傳輸性、該化合物之獲得容易性、該化合物對有機溶劑之溶解性的平衡時,尤以式(D1)表示之經氰基取代之含氮雜芳香族化合物最適宜。
本發明之組成物,於上述經氰基取代之含氮雜芳香族化合物以外,亦可含有雜多酸化合物、芳基磺酸衍生物、四氰基醌二甲烷(tetracyanoquinodimethane)衍生物、苯醌衍生物等之其他摻雜物物質,其中尤以雜多酸為佳。
雜多酸,代表而言係指式(D6)表示之Keggin型或式(D7)表示之Dawson型之化學構造表示之具有雜原子位於分子中心之構造,且為釩(V)、鉬(Mo)、鎢(W)等之含氧酸的同多酸、與異種元素的含氧酸進行縮合而成之聚酸。如此之異種元素的含氧酸,主要可列舉矽(Si)、磷(P)、砷(As)之含氧酸。
雜多酸之具體例子,可列舉磷鉬酸、矽鉬酸、磷鎢酸、矽鎢酸、磷鎢鉬酸等,此等可單獨使用、亦可組合2種以上使用。再者,本發明中所使用之雜多酸,可作為市售品而獲得,又,亦可藉由公知之方法合成。
特別是使用1種之雜多酸時,該1種之雜多酸,較佳為磷鎢酸或磷鉬酸、最適宜為磷鎢酸。又,使用2種以上之雜多酸時,該2種以上之雜多酸之1者,較佳為磷鎢酸或磷鉬酸、更佳為磷鎢酸。
再者,雜多酸,不管是於元素分析等之定量分析中,由一般式表示之構造來看,元素數為多或少,只要其係作為市售品所獲得者、或遵照公知之合成方法而適切地合成者,即可於本發明中使用。
亦即,例如,一般而言磷鎢酸係以化學式H3(PW12O40)‧nH2O表示、磷鉬酸係以化學式H3(PMo12O40)‧nH2O表示,但定量分析中,不管該式中之P(磷)、O(氧)或W(鎢)或Mo(鉬)之數目為多或少,只要其係作為市售品所獲得者、或遵照公知之合成方法而適切地合成者,即可於本發明中使用。此時,本發明所規定之雜多酸的質量,並非合成物或市售品中之純粹的磷鎢酸質量(磷鎢酸含量),而是意指能夠作為市售品而獲得的形態及能夠以公知之合成法單離的形態中,於包含
水合水或其他雜質等的狀態下的全部質量。
本發明之組成物中的摻雜物物質之含量,雖為考量電荷傳輸性物質之種類或量等所適當設定者,但通常以質量比計,相對於電荷傳輸性物質1而言,為0.1~10左右。
本發明之組成物所含有的電荷傳輸性物質,典型而言,可使用於有機EL之領域等中所使用者。
其具體例子,可列舉寡苯胺衍生物、N,N’-二芳基聯苯胺衍生物、N,N,N’,N’-四芳基聯苯胺衍生物等之芳基胺衍生物(苯胺衍生物);寡噻吩衍生物、噻吩并噻吩衍生物、噻吩并苯并噻吩衍生物等之噻吩衍生物等之各種電荷傳輸性化合物。
其中尤以苯胺衍生物、噻吩衍生物為佳;更佳為苯胺衍生物。
本發明中,電荷傳輸性化合物之分子量,就配製賦予平坦性高之薄膜的均勻組成物之觀點而言,較佳為200~9,500左右,但由得到電荷傳輸性更加優異的薄膜之觀點而言,其下限值更佳為300、又更佳為400,就配製更加再現性良好地賦予平坦性高之薄膜的均勻組成物之觀點而言,其上限值更佳為8,000、又更佳為7,000、又再更佳為6,000、又再更佳為5,000。再者,就薄膜化後防止電荷傳輸性物質分離的觀點而言,電荷傳輸性化合物較佳為無分子量分布(分散度為1)(亦即,較佳為單一之分子量)。
苯胺衍生物之具體例子,可列舉下述式(1)或(2)表示者。
式(1)中,k表示1~10之整數,就提高化合物對有機溶劑之溶解性的觀點,較佳為1~5、更佳為1~3、又更佳為1或2、最佳為1。式(2)中,l表示1或2。
式(2)中,R1及R2係互相獨立地表示氫原子、鹵素原子、硝基、氰基、或可經鹵素原子取代之,碳數1~20之烷基、碳數2~20之烯基、碳數2~20之炔基、碳數6~20之芳基或碳數2~20之雜芳基。
鹵素原子可列舉氟原子、氯原子、溴原子、碘原子等,較佳為氟原子。
碳數1~20之烷基,係直鏈狀、分支狀、環狀之任意者均可,可列舉例如甲基、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之直鏈或分支狀烷基;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。
碳數2~20之烯基之具體例子,可列舉乙烯
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。
碳數2~20之炔基之具體例子,可列舉乙炔基、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。
碳數6~20之芳基之具體例子,可列舉苯基、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。
碳數2~20之雜芳基之具體例子,可列舉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-異噁唑基等之含氧雜芳基;2-噻唑基、4-噻唑基、5-噻唑基、3-異噻唑基、4-異噻唑基、5-異噻唑基等之含硫雜芳基;2-咪唑基、4-咪唑基、2-吡啶基、3-吡啶基、4-吡啶基、2-吡嗪基、3-吡嗪基、5-吡嗪基、6-吡嗪基、2-嘧啶基、4-嘧啶基、5-嘧啶基、6-嘧啶基、3-嗒嗪基、4-嗒嗪基、5-嗒嗪基、6-嗒嗪基、1,2,3-三嗪-4-基、1,2,3-三嗪-5-基、1,2,4-三嗪-3-基、1,2,4-三嗪-5-基、1,2,4-三嗪-6-基、1,3,5-三嗪-2-基、1,2,4,5-四嗪-3-基、1,2,3,4-四嗪-5-基、
2-喹啉基、3-喹啉基、4-喹啉基、5-喹啉基、6-喹啉基、7-喹啉基、8-喹啉基、1-異喹啉基、3-異喹啉基、4-異喹啉基、5-異喹啉基、6-異喹啉基、7-異喹啉基、8-異喹啉基、2-喹噁啉基、5-喹噁啉基、6-喹噁啉基、2-喹唑啉基、4-喹唑啉基、5-喹唑啉基、6-喹唑啉基、7-喹唑啉基、8-喹唑啉基、3-辛啉基、4-辛啉基、5-辛啉基、6-辛啉基、7-辛啉基、8-辛啉基等之含氮雜芳基等。
此等之中,R1及R2尤佳為氫原子、氟原子、氰基、可經鹵素原子取代之碳數1~20之烷基、可經鹵素原子取代之碳數6~20之芳基、可經鹵素原子取代之碳數2~20之雜芳基;更佳為氫原子、氟原子、氰基、可經鹵素原子取代之碳數1~10之烷基、可經鹵素原子取代之苯基;又更佳為氫原子、氟原子、甲基、三氟甲基;最佳為氫原子。
式(1)及(2)中,Ph1係表示式(P1)表示之基。
式中,R3~R6係互相獨立地表示氫原子、鹵素原子、硝基、氰基、或可經鹵素原子取代之,碳數1~20之烷基、碳數2~20之烯基、碳數2~20之炔基、碳數6~20之芳基或碳數2~20之雜芳基,此等之具體例子,可列舉與上述R1及R2中說明的為相同者。
特別地,作為R3~R6,較佳為氫原子、氟原子、氰基、可經鹵素原子取代之碳數1~20之烷基、可經鹵素原子取代之碳數6~20之芳基、可經鹵素原子取代之碳數2~20之雜芳基;更佳為氫原子、氟原子、氰基、可經鹵素原子取代之碳數1~10之烷基、可經鹵素原子取代之苯基;又更佳為氫原子、氟原子、甲基、三氟甲基;最佳為氫原子。
以下,列舉作為Ph1之適合的基之具體例子,但不限定於此。
式(1)中,Ar1係互相獨立地表示式(B1)~(B11)之任一者表示之基,特佳為式(B1’)~(B11’)之任一者表示之基。
式中,R7~R27、R30~R51及R53~R154係互相獨立地表示氫原子、鹵素原子、硝基、氰基、或可經鹵素原子取代之,二苯基胺基、碳數1~20之烷基、碳數2~20之烯基、碳數2~20之炔基、碳數6~20之芳基或碳數2~20之雜芳基,R28及R29係互相獨立地表示可經Z1取代之,碳數6~20之芳基或碳數2~20之雜芳基,R52表示氫原子、可經Z4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Z1取代之,碳數6~20之芳基或碳數2~20之雜芳基,Z1表示鹵素原子、硝基、氰
基、或可經Z2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,Z2表示鹵素原子、硝基、氰基、或可經Z3取代之,碳數6~20之芳基或碳數2~20之雜芳基,Z3表示鹵素原子、硝基或氰基,Z4表示鹵素原子、硝基、氰基、或可經Z5取代之,碳數6~20之芳基或碳數2~20之雜芳基,Z5表示鹵素原子、硝基、氰基、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,此等鹵素原子、碳數1~20之烷基、碳數2~20之烯基、碳數2~20之炔基、碳數6~20之芳基及碳數2~20之雜芳基之具體例子,可列舉與上述R1及R2中說明的為相同者。
特別地,作為R7~R27、R30~R51及R53~R154,較佳為氫原子、氟原子、氰基、可經鹵素原子取代之二苯基胺基、可經鹵素原子取代之碳數1~20之烷基、可經鹵素原子取代之碳數6~20之芳基、可經鹵素原子取代之碳數2~20之雜芳基;更佳為氫原子、氟原子、氰基、可經鹵素原子取代之碳數1~10之烷基、可經鹵素原子取代之苯基;又更佳為氫原子、氟原子、甲基、三氟甲基;最佳為氫原子。
作為R28及R29,較佳為可經Z1取代之碳數6~14之芳基、可經Z1取代之碳數2~14之雜芳基;更佳為可經Z1取代之碳數6~14之芳基;又更佳為可經Z1取代之苯基、可經Z1取代之1-萘基、可經Z1取代之2-萘基。
作為R52,較佳為氫原子、可經Z1取代之碳
數6~20之芳基、可經Z1取代之碳數2~20之雜芳基、可經Z4取代之碳數1~20之烷基;更佳為氫原子、可經Z1取代之碳數6~14之芳基、可經Z1取代之碳數2~14之雜芳基、可經Z4取代之碳數1~10之烷基;又更佳為氫原子、可經Z1取代之碳數6~14之芳基、可經Z1取代之碳數2~14之含氮雜芳基、可經Z4取代之碳數1~10之烷基;又再更佳為氫原子、可經Z1取代之苯基、可經Z1取代之1-萘基、可經Z1取代之2-萘基、可經Z1取代之2-吡啶基、可經Z1取代之3-吡啶基、可經Z1取代之4-吡啶基、可經Z4取代之甲基。
Ar4係互相獨立地表示可經各自之芳基係為碳數6~20之芳基的二芳基胺基取代之碳數6~20之芳基。碳數6~20之芳基之具體例子,可列舉與R1及R2中說明的為相同者,上述二芳基胺基之具體例子,可列舉二苯基胺基、1-萘基苯基胺基、二(1-萘基)胺基、1-萘基-2-萘基胺基、二(2-萘基)胺基等。
作為Ar4,較佳為苯基、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、p-(二苯基胺基)苯基、p-(1-萘基苯基胺基)苯基、p-(二(1-萘基)胺基)苯基、p-(1-萘基-2-萘基胺基)苯基、p-(二(2-萘基)胺基)苯基;更佳為p-(二苯基胺基)苯基。
以下,列舉作為Ar1之適合的基之具體例子,但不限定於此等。再者,下述式中,DPA表示二苯基胺
基,R52表示與上述相同意義。
式(1)中,Ar2係互相獨立地表示式(A1)~(A18)之任一者表示之基。
式中,R155表示氫原子、可經Z4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Z1取代之,碳數6~20之芳基或碳數2~20之雜芳基,R156及R157係互相獨立地表示可經Z1取代之,碳數6~20之芳基或碳數2~20之雜芳基,DPA、Ar4、Z1及Z4表示與上述相同意義。此等鹵素原子、碳數1~20之烷基、碳數2~20之烯基、碳數2~20之炔基、碳數6~20之芳基及碳數2~20之雜芳基之具體例子,可列舉與上述R1及R2中說明的為相同者。
特別地,作為R155,較佳為氫原子、可經Z1取代之碳數6~20之芳基、可經Z1取代之碳數2~20之雜
芳基、可經Z4取代之碳數1~20之烷基;更佳為氫原子、可經Z1取代之碳數6~14之芳基、可經Z1取代之碳數2~14之雜芳基、可經Z4取代之碳數1~10之烷基;又更佳為氫原子、可經Z1取代之碳數6~14之芳基、可經Z1取代之碳數2~14之含氮雜芳基、可經Z4取代之碳數1~10之烷基;又再更佳為氫原子、可經Z1取代之苯基、可經Z1取代之1-萘基、可經Z1取代之2-萘基、可經Z1取代之2-吡啶基、可經Z1取代之3-吡啶基、可經Z1取代之4-吡啶基、可經Z4取代之甲基。
作為R156及R157,較佳為可經Z1取代之碳數6~14之芳基、可經Z1取代之碳數2~14之雜芳基;更佳為可經Z1取代之碳數6~14之芳基;又更佳為可經Z1取代之苯基、可經Z1取代之1-萘基、可經Z1取代之2-萘基。
以下,列舉作為Ar2之適合的基之具體例子,但不限定於此等。再者,下述式中,R155及DPA表示與上述相同意義。
式(1)中,考慮到所得之苯胺衍生物的合成容易性時,較佳係Ar1全部為相同之基、且Ar2全部為相同之基;更佳係Ar1及Ar2全部為相同之基。亦即,式(1)表示之苯胺衍生物,更佳為下述式(1-1)表示之苯胺衍生物。
式(1-1)中,Ph1及k表示與上述相同意義,Ar5係同時表示式(D1)~(D13)之任一者表示之基,特佳為式(D1’)~(D13’)之任一者表示之基。再者,下述式中,R28、R29、R52、Ar4及DPA表示與上述相同意義。Ar5之具體例子,可列舉與上述作為Ar1之適合的基之具體例子的為相同者。
又,如後述般,由於可使用價格較便宜之雙(4-胺基苯基)胺作為原料化合物來比較簡便地合成,而且所得之苯胺衍生物對有機溶劑的溶解性優良,式(1)表示之苯胺衍生物,較佳為式(1-2)表示之苯胺衍生物。
式中,Ar6係同時地表示式(E1)~(E14)之任一者表示之基。再者,下述式中,R52表示與上述相同意義。
式(2)中,Ar3表示式(C1)~(C8)之任一者表示之基,特佳為(C1’)~(C8’)之任一者表示之基。再者,下述式中,DPA表示與上述相同意義。
R28、R29、R52及R155~R157中,Z1較佳為鹵素原子、硝基、氰基、可經Z2取代之碳數1~10之烷基、可經Z2取代之碳數2~10之烯基、可經Z2取代之碳數2~10之炔基;更佳為鹵素原子、硝基、氰基、可經Z2取代之碳數1~3之烷基、可經Z2取代之碳數2~3之烯基、可經Z2取代之碳數2~3之炔基;又更佳為氟原子、可經Z2取代之碳數1~3之烷基、可經Z2取代之碳數2~3之烯基、
可經Z2取代之碳數2~3之炔基。
R28、R29、R52及R155~R157中,Z4較佳為鹵素原子、硝基、氰基、可經Z5取代之碳數6~14之芳基;更佳為鹵素原子、硝基、氰基、可經Z5取代之碳數6~10之芳基;又更佳為氟原子、可經Z5取代之碳數6~10之芳基;又再更佳為氟原子、可經Z5取代之苯基。
R28、R29、R52及R155~R157中,Z2較佳為鹵素原子、硝基、氰基、可經Z3取代之碳數6~14之芳基;更佳為鹵素原子、硝基、氰基、可經Z3取代之碳數6~10之芳基;又更佳為氟原子、可經Z3取代之碳數6~10之芳基;又再更佳為氟原子、可經Z3取代之苯基。
R28、R29、R52及R155~R157中,Z5較佳為鹵素原子、硝基、氰基、可經Z3取代之碳數1~10之烷基、可經Z3取代之碳數2~10之烯基、可經Z3取代之碳數2~10之炔基;更佳為鹵素原子、硝基、氰基、可經Z3取代之碳數1~3之烷基、可經Z3取代之碳數2~3之烯基、可經Z3取代之碳數2~3之炔基;又更佳為氟原子、可經Z3取代之碳數1~3之烷基、可經Z3取代之碳數2~3之烯基、可經Z3取代之碳數2~3之炔基。
R28、R29、R52及R155~R157中,Z3較佳為鹵素原子、更佳為氟原子。
R7~R27、R30~R51及R53~R154中,Z1較佳為鹵素原子、硝基、氰基、可經Z2取代之碳數1~3之烷基、可經Z2取代之碳數2~3之烯基、可經Z2取代之碳數2~3
之炔基;更佳為鹵素原子、可經Z2取代之碳數1~3之烷基;又更佳為氟原子、可經Z2取代之甲基。
R7~R27、R30~R51及R53~R154中,Z4較佳為鹵素原子、硝基、氰基、可經Z5取代之碳數6~10之芳基;更佳為鹵素原子、可經Z5取代之碳數6~10之芳基;又更佳為氟原子、可經Z5取代之苯基。
R7~R27、R30~R51及R53~R154中,Z2較佳為鹵素原子、硝基、氰基、可經Z3取代之碳數6~10之芳基;更佳為鹵素原子、可經Z3取代之碳數6~10之芳基;又更佳為氟原子、可經Z3取代之苯基。
R7~R27、R30~R51及R53~R154中,Z5較佳為鹵素原子、硝基、氰基、可經Z3取代之碳數1~3之烷基、可經Z3取代之碳數2~3之烯基、可經Z3取代之碳數2~3之炔基;更佳為鹵素原子、可經Z3取代之碳數1~3之烷基;又更佳為氟原子、可經Z3取代之甲基。
R7~R27、R30~R51及R53~R154中,Z3較佳為鹵素原子、更佳為氟原子。
本發明中,作為R52及R155之適合的基之具體例子,可列舉以下所示者,但不限定於此等。
本發明中,上述烷基、烯基及炔基之碳數,較佳為10以下、更佳為6以下、又更較佳為4以下。又,上述芳基及雜芳基之碳數,較佳為14以下、更佳為10以下、又更佳為6以下。
式(1)表示之苯胺衍生物,可使式(3)表示之胺化合物與式(4)表示之芳基化合物,於觸媒存在下反應而製造。
特別地,式(1-1)表示之苯胺衍生物,可使式(7)表示之胺化合物與式(8)表示之芳基化合物,於觸媒存在下反應而製造。
又,式(1-2)表示之苯胺衍生物,可使雙(4-胺基苯基)胺與式(9)表示之芳基化合物,於觸媒存在下反應而製造。
另一方面,式(2)表示之苯胺衍生物,可使
式(5)表示之胺化合物與式(6)表示之芳基化合物,於觸媒存在下反應而製造。
鹵素原子可列舉與上述相同者。擬鹵素基可列舉甲烷磺醯氧基、三氟甲烷磺醯氧基、九氟丁烷磺醯氧基等之(氟)烷基磺醯氧基;苯磺醯氧基、甲苯磺醯氧基等之芳香族磺醯氧基等。
式(3)、(5)或(7)表示之胺化合物或雙(4-胺基苯基)胺;與式(4)、(6)、(8)或(9)表示之芳基化合物的用量比,相對於胺化合物或雙(4-胺基苯基)胺之全部NH基之物質量而言,可使芳基化合物為等量以上,但較宜為1~1.2當量左右。
上述反應所用之觸媒,可列舉例如氯化銅、溴化銅、碘化銅等之銅觸媒;肆(三苯基膦)鈀(Pd(PPh3)4)、雙(三苯基膦)二氯鈀(Pd(PPh3)2Cl2)、雙(二亞苄基丙酮)鈀(Pd(dba)2)、參(二亞苄基丙酮)二鈀(Pd2(dba)3)、雙(三(t-丁基膦)鈀(Pd(P-t-Bu3)2)、乙酸鈀(Pd(OAc)2)等之鈀觸媒
等。此等之觸媒,可1種單獨使用、亦可組合2種以上使用。又,此等之觸媒亦可與公知之適切的配位子一起使用。
如此之配位子,可列舉三苯基膦、三-o-甲苯基膦、二苯基甲基膦、苯基二甲基膦、三甲基膦、三乙基膦、三丁基膦、三-t-丁基膦、二-t-丁基(苯基)膦、二-t-丁基(4-二甲基胺基苯基)膦、1,2-雙(二苯基膦基)乙烷、1,3-雙(二苯基膦基)丙烷、1,4-雙(二苯基膦基)丁烷、1,1’-雙(二苯基膦基)二茂鐵等之3級膦;亞磷酸三甲酯、亞磷酸三乙酯、亞磷酸三苯酯等之3級亞磷酸酯等。
觸媒之使用量,相對於式(4)、(6)、(8)或(9)表示之芳基化合物1mol而言,可為0.2mol左右,較適宜為0.15mol左右。又,使用配位子時,其使用量,相對於所使用之金屬錯合物而言,可為0.1~5當量,較適宜為1~2當量。
原料化合物全部為固體的情況時或就效率良好地得到目標之苯胺衍生物的觀點而言,上述各反應係於溶劑中進行。使用溶劑時,只要係對反應不會造成不良影響者,其種類並無特殊限定。其具體例子,可列舉脂肪族烴類(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-二甲苯、m-二甲苯、p-二甲苯、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)、尿素類(N,N-二甲基咪唑啉酮、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。此等之溶劑,可1種單獨使用、亦可混合2種以上使用。
反應溫度,只要於所使用之溶劑的融點至沸點的範圍內適當設定即可,特別以0~200℃左右為佳、更佳為20~150℃。
反應結束後,可依一般方法進行後處理,得到目標之苯胺衍生物。
上述式(1)表示之苯胺衍生物之製造方法中,可使作為原料使用的式(3’)表示之胺化合物,可使式(10)表示之胺化合物與式(11)表示之芳基化合物,於觸媒存在下反應而效率良好地製造。
式(3’)表示之胺化合物之上述製造方法,係為使式(10)表示之胺化合物與式(11)表示之芳基化合物進行偶合反應者,式(10)表示之胺化合物與式(11)表示之芳基化合物之用量,以物質量比計,相對於胺化合物1而言,以芳基化合物2~2.4左右為適宜。
關於上述偶合反應中之觸媒、配位子、溶劑、反應溫度等的各條件,係與關於式(1)表示之苯胺衍生物之製造方法所說明的上述條件相同。
式(1)中,當製造Ar1為R52為氫原子之式(B4)表示之基或式(B10)表示之基、或者Ar2為式(A12)表示之基或R155(包含式(1-1)中之R52)為氫原子之式(A16)表示之基的本發明之苯胺衍生物的情況時,上述反應中,亦可使用於胺基上具有保護基之芳基化合物。
具體而言,上述反應中,係分別使用如下各式之各芳基化合物的胺基被保護之芳基化合物(式(G1P)~(G6P)),來取代Ar2為式(A12)表示之基的式(4)表示之芳基化合物(式(G1))、Ar2為式(A16)表示之基且R155為氫原子的式(4)表示之芳基化合物(式(G2))、Ar5為式(D9)表示之基的式(8)表示之芳基化合物(式(G1))、Ar5為式(D11)表示之基且R52為氫原子的式(8)表示之芳基化合物(式(G2))、Ar6為式(E13)表示之基且R52為氫原子的式(9)表示之芳基化合物(式(G3))、Ar6為式
(E14)表示之基且R52為氫原子的式(9)表示之芳基化合物(式(G4))、Ar1為式(B4)表示之基且R52為氫原子的式(11)表示之芳基化合物(式(G5))、Ar1為式(B10)表示之基的式(11)表示之芳基化合物(式(G6)),使此等經保護之芳基化合物與上述胺化合物在觸媒存在下反應後,於適當的時機進行脫保護。
P1~P6係互相獨立地表示胺基之保護基。如此之保護基,可使用慣用之保護基,具體而言,可列舉取代或非取代之烷氧基羰基(例如甲氧基羰基、乙氧基羰基、t-丁氧基羰基、2,2,2-三氯乙氧基羰基、烯丙氧基羰基、9-茀基甲氧基羰基)、取代或非取代之芳烷氧基羰基(例如
苄氧基羰基)、取代或非取代之芳氧基羰基(例如苯氧基羰基)等之氧基羰基型保護基;甲醯基;取代或非取代之烷醯基(例如乙醯基、三氟乙醯基、t-丁醯基)、取代或非取代之芳基羰基(例如苄醯基)等之羰基型保護基;取代或非取代之烷基(例如、t-丁基)、取代或非取代之芳烷基(例如苄基、二苯甲基(benzhydryl)、三苯甲基(trityl))等之烷基型保護基、取代或非取代之磺醯基型保護基(例如苯磺醯基、p-甲苯磺醯基、2-硝基苯磺醯基)等,但不限定於此等。其中尤以氧基羰基型保護基、羰基型保護基、烷基型保護基為佳。
再者,Ar51~Ar56及Ar61~Ar66,係表示分別將各個芳基化合物之X(鹵素原子或擬鹵素基)予以去除所表示之1價基。例如,Ar61~Ar66係分別表示下述之基。
關於使用了上述之具有胺基之保護基的芳基化合物之製造方法,更具體的例子可列舉以下所示者,但不限定於此等。
使用了如此之具有保護基的芳基化合物之製造方法中,關於原料之用量比、觸媒、配位子、溶劑、反應溫度等的各條件,係與關於式(1)表示之苯胺衍生物或式(3’)表示之胺化合物所說明之上述條件相同。又,脫保護係於酸性或鹼性條件下進行處理、於氧化或還原條件下進行處理等,例如參考GREEN’S PROTECTIVE GROUPS in Organic Synthesis,4th Edition,考慮保護基之性質等以適當之公知方法進行即可。
當製造式(1)中,Ar1為R52不為氫原子之式(B4)表示之基、或式(B11)表示之基;或者Ar2為式(A13)表示之基、或R155(包含式(1-1)中之R52)不為氫原子之式(A16)表示之基的具有3級胺部位的本發明之苯胺衍生物的情況時,亦可使用Ar1為式(B4)表示之基且R52為氫原子或式(B10)表示之基、或Ar2為式(A12)表示之基或式(A16)表示之基且R155(包含式(1-1)中之R52)為氫原子的以式(1)表示之具有2級胺部位的本發明之苯胺衍生物;或Ar1為R52為氫原子之式(B4)表示之基或式(B10)表示之基的以式(3)表示之具有2級胺部位的胺化合物。
具體而言,係如以下所示,使具有該2級胺部位的苯胺衍生物或胺化合物中之胺部位、與式(10)表示之芳基化合物或式(11)或(12)表示之烴化合物反應。
式中,X、R139~R146、Ar4及R45~R51表示與上述相同意義。Cb155及Cb52係互相獨立地表示可經Z4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Z1取代之,碳數6~20之芳基或碳數2~20之雜芳基,此等烷基、烯基、炔基、芳基及雜芳基可列舉與上述相同者。Z1及Z4表示與上述相同意義。
關於使用了上述具有2級胺部位的苯胺衍生物或胺化合物之製造方法,更具體的例子可列舉以下所示者,但不限定於此等。
式(1-3)~(1-8)表示之苯胺衍生物、與式(10)表示之芳基化合物或式(11)~(12)表示之烴化合物之用量比,相對於苯胺衍生物之全部NH基之物質量而言,可使芳基化合物或烴化合物為等量以上,但較宜為1~1.2當量左右。
又,式(3’-1)~(3’-2)表示之胺化合物、與式(10)表示之芳基化合物或式(12)表示之烴化合物之用量比,以物質量比計,相對於式(3’-1)~(3’-2)表示之胺化合物1而言,式(10)表示之芳基化合物或式(12)表示之烴化合物2~2.4左右為適宜。
其他,用量以外之各條件,係如以下所述。
使用銅、鈀等之上述觸媒,來製造式(1-9)~(1-14)表示之苯胺衍生物或式(3’-3)~(3’-4)表示之胺化合物的情況時,關於觸媒、配位子、溶劑、反應溫度等之
條件,可採用關於式(1)表示之苯胺衍生物之製造方法所說明的上述條件。
另一方面,藉由使用了式(1)表示之芳基化合物、Cb155為可經Z4取代之碳數1~20之烷基或可經Z1取代之,碳數6~20之芳基或碳數2~20之雜芳基的式(11)表示之烴化合物、或Cb52為可經Z4取代之碳數1~20之烷基或可經Z1取代之,碳數6~20之芳基或碳數2~20之雜芳基的式(12)表示之烴化合物的取代反應,來製造式(1-9)~(1-14)表示之苯胺衍生物或式(3’-3)~(3’-4)表示之胺化合物的情況時,係於溶劑中,使式(1-3)~(1-8)表示之苯胺衍生物或式(3’-1)~(3’-2)表示之胺化合物與鹼反應,再使所得到之生成物與式(11)~(12)表示之烴化合物或式(10)表示之芳基化合物反應。
鹼可列舉鋰、鈉、鉀、氫化鋰、氫化鈉、氫氧化鉀、t-丁氧基鋰、t-丁氧基鈉、t-丁氧基鉀、氫氧化鋰、氫氧化鈉、氫氧化鉀、碳酸鈉、碳酸鉀、碳酸氫鈉、碳酸氫鉀等之鹼金屬單質;氫氧化鹼金屬、烷氧基鹼金屬、碳酸鹼金屬、碳酸氫鹼金屬;碳酸鈣等之碳酸鹼土類金屬;n-丁基鋰、s-丁基鋰、t-丁基鋰等之有機鋰;三乙胺、二異丙基乙胺、四甲基乙二胺、三乙二胺、吡啶等之胺類等,但只要係此種反應所使用者,則無特殊限定。特別地,由操作容易而言,以氫化鈉、碳酸鈉、碳酸鉀為適宜。
鹼之使用量,分別地相對於式(1-3)~(1-8)表示之苯胺衍生物之全部NH基而言,為1~1.2當量左右,相對於式(3’-1)~(3’-2)表示之胺化合物1mol而言,為2~2.4左右。
溶劑之具體例子,可列舉關於式(1)表示之苯胺衍生物之製造方法所例示的溶劑。反應溫度只要係於所使用之溶劑的融點至沸點之範圍內適當設定即可,但為20~150℃左右。
反應結束後,係遵照分液處理、管柱層析、再沈澱、再結晶等的一般方法來進行後處理。
再者,雖然因為會依原料之構造或所用之溶劑種類等而受到影響,無法一概而論,但X為氟原子時較佳為取代反應、X為氟原子以外時,較佳為使用觸媒之反應。
又,上述式(1)表示之苯胺衍生物之製造方法中可作為原料使用的2個Ar1均為式(B1)表示之基的式(3)表示之胺化合物,亦可遵照國際公開第2008/129947號或國際公開第2013/08466號記載之方法來合成。
以下,列舉式(1)或(2)表示之苯胺衍生物的具體例子,但不限定於此等。再者,式中,「Me」表示甲基、「Et」表示乙基、「Prn」表示n-丙基、「Pri」表示i-丙基、「Bun」表示n-丁基、「Bui」表示i-丁基、「Bus」表示s-丁基、「But」表示t-丁基、
「DPA」表示二苯基胺基、「SBF」表示9,9’-螺二[9H-茀]-2-基。
本發明之組成物所含有的有機溶劑,可使用可良好地溶解電荷傳輸性物質及摻雜物物質之良溶劑。
如此之良溶劑,可列舉例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N,N-二甲基丁醯胺、N,N-二乙基丁醯胺、N,N-甲基乙基丁醯胺、N,N-二甲基異丁醯胺、N,N-二乙基異丁醯胺、N-乙基-N-甲基異丁醯胺、N-甲基吡咯啶酮、1,3-二甲基-2-咪唑啉酮等之有機溶劑,但不限定於此等。此等溶劑可1種單獨、或混合2種以上使用,其使用量,相對於所使用之溶劑全體而言,可為5~100質量%。
又,本發明中,以提高對基板之可濕性、調
整溶劑之表面張力、調整極性、調整沸點等為目的,於上述有機溶劑以外,亦可含有其他有機溶劑。如此之其他有機溶劑,較佳為包含二醇類、三醇類、烷二醇單烷基醚類、烷二醇二烷基醚類、二烷二醇單烷基醚類、二烷二醇二烷基醚類,可列舉二醇類、烷二醇單烷基醚類、二烷二醇單烷基醚類等,但不限定於此等。此等溶劑可1種單獨、或混合2種以上使用,其使用量係依一起使用的良溶劑之量來決定。
其中,良溶劑以外之其他有機溶劑,尤以二乙二醇、三乙二醇、二丙二醇、1,2-乙二醇、1,2-丙二醇、1,2-丁二醇、2,3-丁二醇、1,3-丁二醇、1,4-丁二醇、乙二醇單甲基醚、乙二醇單乙基醚、乙二醇丙基醚、乙二醇異丙基醚、乙二醇單丁基醚、乙二醇單異丁基醚、丙二醇單甲基醚、丙二醇單乙基醚、丙二醇單丙基醚、丙二醇單異丙基醚、丙二醇單丁基醚、丙二醇單異丁基醚二乙二醇單甲基醚、二乙二醇單乙基醚、二乙二醇丙基醚、二乙二醇異丙基醚、二乙二醇單丁基醚、二乙二醇單異丁基醚、二丙二醇單甲基醚、二丙二醇單乙基醚、二丙二醇單丙基醚、二丙二醇單異丙基醚、二丙二醇單丁基醚、二丙二醇單異丁基醚為佳;更佳為二乙二醇、三乙二醇、二丙二醇、1,2-乙二醇、1,2-丙二醇、1,2-丁二醇、2,3-丁二醇、1,3-丁二醇、1,4-丁二醇、乙二醇單甲基醚、丙二醇單甲基醚、二乙二醇單甲基醚、二丙二醇單甲基醚。藉由一邊考慮電荷傳輸性物質或摻雜物物質之種類或量,一邊
由如此之溶劑中選擇所用的溶劑,可容易地配製具有所期望之液體物性的組成物。
本發明中,由得到平坦性優良之電荷傳輸性的觀點而言,上述電荷傳輸性物質及上述摻雜物物質,係溶解於上述有機溶劑中(含有有機矽烷化合物等之其他成分時,該成分亦溶解於上述有機溶劑中)。
本發明之組成物的黏度,雖為依照所製作之薄膜的厚度等或固體成分濃度而適當設定者,但通常於25℃為1~50mPa‧s,其表面張力,通常為20~50mN/m。
本發明之組成物,亦可含有有機矽烷化合物。藉由含有有機矽烷化合物,於使用由組成物所得到之薄膜作為有機EL元件之電洞注入層時,可提高對電洞傳輸層或發光層等於與陽極相反側以鄰接於電洞注入層的方式層合的層之電洞注入能力。
該有機矽烷化合物,可列舉二烷氧基矽烷化合物、三烷氧基矽烷化合物或四烷氧基矽烷化合物,此等可單獨使用、亦可組合2種以上使用。
本發明中,有機矽烷化合物,較佳為包含由二烷氧基矽烷化合物及三烷氧基矽烷化合物中選出之1種;更佳為包含三烷氧基矽烷化合物;又更佳為包含含有氟原子之三烷氧基矽烷化合物。
此等之烷氧基矽烷化合物,可列舉例如以式(S1)~(S3)表示者。
Si(OR)4 (S1)
SiR’(OR)3 (S2)
Si(R’)2(OR)2 (S3)
式中,R係互相獨立地表示可經Z6取代之碳數1~20之烷基、可經Z6取代之碳數2~20之烯基、可經Z6取代之碳數2~20之炔基、可經Z7取代之碳數6~20之芳基、或可經Z7取代之碳數2~20之雜芳基,R’係互相獨立地表示可經Z8取代之碳數1~20之烷基、可經Z8取代之碳數2~20之烯基、可經Z8取代之碳數2~20之炔基、可經Z9取代之碳數6~20之芳基、或可經Z9取代之碳數2~20之雜芳基。
Z6表示鹵素原子、可經Z10取代之碳數6~20之芳基、或可經Z10取代之碳數2~20之雜芳基,Z7表示鹵素原子、可經Z10取代之碳數1~20之烷基、可經Z10取代之碳數2~20之烯基、或可經Z10取代之碳數2~20之炔基。
Z8表示鹵素原子、可經Z10取代之碳數6~20之芳基、可經Z10取代之碳數2~20之雜芳基、環氧基環己基、環氧丙氧基、甲基丙烯醯氧基、丙烯醯氧基、脲基(-NHCONH2)、硫醇基、異氰酸酯基(-NCO)、胺基、-NHY1基、或NY2Y3基,Z9表示鹵素原子、可經Z10取代之碳數1~20之烷基、可經Z10取代之碳數2~20之烯基、可經Z10取代之碳數2~20之炔基、環氧基環己基、環氧丙氧基、甲基丙烯醯氧基、丙烯醯氧基、脲基(-NHCONH2)、硫醇基、異氰酸酯基(-NCO)、胺基、-NHY1基、或
NY2Y3基,Y1~Y3係互相獨立地表示可經Z10取代之碳數1~20之烷基、可經Z10取代之碳數2~20之烯基、可經Z10取代之碳數2~20之炔基、可經Z10取代之碳數6~20之芳基、或可經Z10取代之碳數2~20之雜芳基。
Z10表示鹵素原子、胺基、硝基、氰基或硫醇基。
式(S1)~(S3)中,鹵素原子、碳數1~20之烷基、碳數2~20之烯基、碳數2~20之炔基、碳數6~20之芳基、及碳數2~20之雜芳基,可列舉與上述相同者。
R及R’中,烷基、烯基及炔基之碳數,較佳為10以下、更佳為6以下、又更佳為4以下。
又,芳基及雜芳基之碳數,較佳為14以下、更佳為10以下、又更佳為6以下。
作為R,較佳為可經Z6取代之,碳數1~20之烷基或碳數2~20之烯基、或可經Z7取代之碳數6~20之芳基;更佳為可經Z6取代之,碳數1~6之烷基或碳數2~6之烯基、或可經Z7取代之苯基;又更佳為可經Z6取代之碳數1~4之烷基或可經Z7取代之苯基;又再更佳為可經Z6取代之,甲基或乙基。
又,作為R’,較佳為可經Z8取代之碳數1~20之烷基或可經Z9取代之碳數6~20之芳基;更佳為可經Z8取代之碳數1~10之烷基或可經Z9取代之碳數6~14之芳基;又更佳為可經Z8取代之碳數1~6之烷基、或可經Z9取代之碳數6~10之芳基;又再更佳為可經Z8取代之碳數1~4
之烷基或可經Z9取代之苯基。
再者,複數個R,可全為相同、亦可相異,複數個R’,亦可全為相同、亦可相異。
作為Z6,較佳為鹵素原子或可經Z10取代之碳數6~20之芳基;更佳為氟原子或可經Z10取代之苯基;最佳為不存在(亦即非取代)。
又,作為Z7,較佳為鹵素原子或可經Z10取代之碳數6~20之烷基;更佳為氟原子或可經Z10取代之碳數1~10之烷基;最佳為不存在(亦即非取代)。
另一方面,作為Z8,較佳為鹵素原子、可經Z10取代之苯基、可經Z10取代之呋喃基、環氧基環己基、環氧丙氧基、甲基丙烯醯氧基、丙烯醯氧基、脲基、硫醇基、異氰酸酯基、胺基、可經Z10取代之苯基胺基、或可經Z10取代之二苯基胺基;更佳為鹵素原子;又更佳為氟原子、或不存在(亦即非取代)。
又,作為Z9,較佳為鹵素原子、可經Z10取代之碳數1~20之烷基、可經Z10取代之呋喃基、環氧基環己基、環氧丙氧基、甲基丙烯醯氧基、丙烯醯氧基、脲基、硫醇基、異氰酸酯基、胺基、可經Z10取代之苯基胺基、或可經Z10取代之二苯基胺基;更佳為鹵素原子;又更佳為氟原子、或不存在(亦即非取代)。
而作為Z10,較佳為鹵素原子、更佳為氟原子或不存在(亦即非取代)。
以下,列舉本發明中可使用之有機矽烷化合
物的具體例子,但不限定於此等。
二烷氧基矽烷化合物之具體例子,可列舉二甲基二甲氧基矽烷、二甲基二乙氧基矽烷、甲基乙基二甲氧基矽烷、二乙基二甲氧基矽烷、二乙基二乙氧基矽烷、甲基丙基二甲氧基矽烷、甲基丙基二乙氧基矽烷、二異丙基二甲氧基矽烷、苯基甲基二甲氧基矽烷、乙烯基甲基二甲氧基矽烷、3-環氧丙氧基丙基甲基二甲氧基矽烷、3-環氧丙氧基丙基甲基二乙氧基矽烷、3-(3,4-環氧基環己基)乙基甲基二甲氧基矽烷、3-甲基丙烯醯氧基丙基甲基二甲氧基矽烷、3-甲基丙烯醯氧基丙基甲基二乙氧基矽烷、3-巰基丙基甲基二甲氧基矽烷、γ-胺基丙基甲基二乙氧基矽烷、N-(2-胺基乙基)胺基丙基甲基二甲氧基矽烷、3,3,3-三氟丙基甲基二甲氧基矽烷等。
三烷氧基矽烷化合物之具體例子,可列舉甲基三甲氧基矽烷、甲基三乙氧基矽烷、乙基三甲氧基矽烷、乙基三乙氧基矽烷、丙基三甲氧基矽烷、丙基三乙氧基矽烷、丁基三甲氧基矽烷、丁基三乙氧基矽烷、戊基三甲氧基矽烷、戊基三乙氧基矽烷、庚基三甲氧基矽烷、庚基三乙氧基矽烷、辛基三甲氧基矽烷、辛基三乙氧基矽烷、十二烷基三甲氧基矽烷、十二烷基三乙氧基矽烷、十六烷基三甲氧基矽烷、十六烷基三乙氧基矽烷、十八烷基三甲氧基矽烷、十八烷基三乙氧基矽烷、苯基三甲氧基矽烷、苯基三乙氧基矽烷、乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、γ-胺基丙基三甲氧基矽烷、3-胺基丙基三
乙氧基矽烷、γ-環氧丙氧基丙基三甲氧基矽烷、3-環氧丙氧基丙基三乙氧基矽烷、γ-甲基丙烯醯氧基丙基三甲氧基矽烷、γ-甲基丙烯醯氧基丙基三乙氧基矽烷、三乙氧基(4-(三氟甲基)苯基)矽烷、十二烷基三乙氧基矽烷、3,3,3-三氟丙基三甲氧基矽烷、(三乙氧基矽烷基)環己烷、全氟辛基乙基三乙氧基矽烷、三乙氧基氟矽烷、十三氟-1,1,2,2-四氫辛基三乙氧基矽烷、五氟苯基三甲氧基矽烷、五氟苯基三乙氧基矽烷、3-(七氟異丙氧基)丙基三乙氧基矽烷、十七氟-1,1,2,2-四氫癸基三乙氧基矽烷、三乙氧基-2-噻吩基矽烷、3-(三乙氧基矽烷基)呋喃等。
四烷氧基矽烷化合物之具體例子,可列舉四乙氧基矽烷、四甲氧基矽烷、四丙氧基矽烷等。
此等之中,尤以3,3,3-三氟丙基甲基二甲氧基矽烷、三乙氧基(4-(三氟甲基)苯基)矽烷、3,3,3-三氟丙基三甲氧基矽烷、全氟辛基乙基三乙氧基矽烷或五氟苯基三甲氧基矽烷、五氟苯基三乙氧基矽烷為佳。
本發明之組成物含有有機矽烷化合物時,其含量,相對於電荷傳輸性物質及摻雜物物質之總質量而言,通常為0.1~50質量%左右,但考慮到抑制所得薄膜之電荷傳輸性降低、且提高對以鄰接於由該組成物所得之薄膜所成的電洞注入層的方式層合於上述陰極側之電洞傳輸層等的電洞注入能力時,較佳為0.5~40質量%左右、更佳為0.8~30質量%左右、又更佳為1~20質量%左右。
本發明之組成物的黏度,雖為依照所製作之薄膜的厚度等或固體成分濃度而適當設定者,但通常於25℃為1~50mPa‧s,其表面張力,通常為20~50mN/m。
又,本發明之組成物的固體成分濃度,雖為考量組成物之黏度及表面張力等、或所製作之薄膜的厚度等而適當設定者,但通常為0.1~20.0質量%左右,考慮到提高組成物之塗佈性時,較佳為0.5~10.0質量%左右、更佳為1.0~5.0質量%左右。再者,此處所稱之固體成分,意指本發明之組成物中所含的電荷傳輸性物質及摻雜物物質。
組成物之配製法並無特殊限定,可列舉例如先使電荷傳輸性物質溶解於溶劑,對其添加摻雜物物質之手法;或使電荷傳輸性物質、摻雜物物質之混合物溶解於溶劑之手法。
又,有機溶劑有複數種時,可於會充分溶解電荷傳輸性物質及摻雜物物質的溶劑中,首先使此等溶解,再對其添加其他溶劑,亦可於複數種有機溶劑之混合溶劑中,依次或同時溶解電荷傳輸性物質及摻雜物物質。
本發明中,由再現性良好地得到高平坦性薄膜之觀點,組成物較佳為於使電荷傳輸性物質、摻雜物物質等溶解於有機溶劑後,使用次微米級之過濾器等來過濾。
本發明之電荷傳輸性薄膜,可藉由將上述說明之本發明之電荷傳輸性薄膜形成組成物塗佈於基材上並燒成,而形成於基材上。
組成物之塗佈方法可列舉浸漬法、旋轉塗佈法、轉印印刷法、輥塗佈法、刷毛塗佈、噴墨法、噴霧法、狹縫塗佈等,但不限定於此等。考慮到再現性良好地得到平坦性高之電荷傳輸薄膜時,塗佈方法較佳為旋轉塗佈法、噴墨法、噴霧法。再者,較佳為依照塗佈方法,來調節組成物之黏度及表面張力。
本發明中,為了再現性良好地得到具有均勻的成膜面及高電荷傳輸性之厚膜的電荷傳輸性膜,較佳為將組成物於大氣環境下燒成。
燒成溫度,雖為考量所得之薄膜的用途、對所得薄膜所賦予之電荷傳輸性的程度、溶劑之種類或沸點等,於100~260℃左右的範圍內適當設定者,但使用所得之薄膜作為有機EL元件之電洞注入層時,較佳為140~250℃左右、更佳為145~240℃左右。燒成時間,雖依燒成溫度而異,故無法一概而論,但通常為1分鐘~1小時。
再者,燒成時,亦可以展現更高之均勻成膜性、或於基材上使反應進行為目的,賦予2階段以上之溫度變化,加熱只要使用例如加熱板或烘箱等適當的機器來進行即可。
電荷傳輸性薄膜之膜厚並無特殊限定,但使用作為有機EL元件之電洞注入層的情況時,較佳為5~200nm。使膜厚變化之方法,係有使組成物中之固體成分濃度變化、或使塗佈時之基板上的溶液量變化等之方
法。
本發明之電荷傳輸性薄膜,於有機EL元件中,可適合使用作為電洞注入層,但亦可使用作為電洞注入傳輸層等之電荷傳輸性功能層。
本發明之有機EL元件,係具有一對電極,且於此等電極之間,具有前述本發明之電荷傳輸性薄膜者。
有機EL元件之代表性的構成,可列舉下述(a)~(f),但不限定於此等。再者,下述構成中,亦可依需要,於發光層與陽極之間設置電子阻擋層等、於發光層與陰極之間設置空穴(電洞)阻擋層等。又,電洞注入層、電洞傳輸層或電洞注入傳輸層亦可兼具作為電子阻擋層等之功能,電子注入層、電子傳輸層或電子注入傳輸層亦可兼具作為空穴(電洞)阻擋層等之功能。
(a)陽極/電洞注入層/電洞傳輸層/發光層/電子傳輸層/電子注入層/陰極
(b)陽極/電洞注入層/電洞傳輸層/發光層/電子注入傳輸層/陰極
(c)陽極/電洞注入傳輸層/發光層/電子傳輸層/電子注入層/陰極
(d)陽極/電洞注入傳輸層/發光層/電子注入傳輸層/陰極
(e)陽極/電洞注入層/電洞傳輸層/發光層/陰極
(f)陽極/電洞注入傳輸層/發光層/陰極
「電洞注入層」、「電洞傳輸層」及「電洞
注入傳輸層」,係指於發光層與陽極之間所形成之層,且具有將電洞由陽極對發光層傳輸之功能者。於發光層與陽極之間僅設有1層之電洞傳輸性材料之層時,其為「電洞注入傳輸層」,於發光層與陽極之間設有2層以上之電洞傳輸性材料之層時,較接近陽極之層為「電洞注入層」,其以外之層為「電洞傳輸層」。特別地,電洞注入層及電洞注入傳輸層,係使用不僅來自陽極之電洞接受性,且分別對電洞傳輸層及發光層之電洞注入性亦優良的薄膜。
「電子注入層」、「電子傳輸層」及「電子注入傳輸層」,係指於發光層與陰極之間所形成之層,且具有將電子由陰極對發光層傳輸之功能者。於發光層與陰極之間僅設有1層之電子傳輸性材料之層時,其為「電子注入傳輸層」,於發光層與陰極之間設有2層以上之電子傳輸性材料之層時,較接近陰極之層為「電子注入層」,其以外之層為「電子傳輸層」。
「發光層」係指具有發光功能之有機層,採用摻雜系統時,係含有主體材料與摻雜物材料。此時,主體材料係主要具有促進電子與電洞之再結合,將激子關閉在發光層內之功能,摻雜物材料,具有使因再結合而得到之激子有效率地發光之功能。磷光元件的情況時,主體材料主要具有將由摻雜物所生成之激子關閉在發光層內之功能。
使用本發明之組成物來製作有機EL元件時的使用材料或製作方法,可列舉如下述者,但不限定於此
等。
所使用之電極基板,較佳為以洗劑、醇、純水等預先進行液體洗淨而先淨化,例如,於陽極基板時,較佳為於臨使用前進行UV臭氧處理、氧-電漿處理等之表面處理。惟,陽極材料以有機物為主成分時,亦可不進行表面處理。
由本發明之組成物所得到之薄膜為電洞注入層時,本發明之有機EL元件之製作方法的一例,係如以下所述。
藉由前述方法,於陽極基板上塗佈本發明之組成物並燒成,於電極上製作電洞注入層。於此電洞注入層之上,依序設置電洞傳輸層、發光層、電子傳輸層、電子注入層、陰極。電洞傳輸層、發光層、電子傳輸層及電子注入層,係依所用之材料的特性等,以蒸鍍法或塗佈法(濕式製程)的任一者形成即可。
陽極材料可列舉以銦錫氧化物(ITO)、銦鋅氧化物(IZO)為代表之透明電極、或由以鋁為代表之金屬或此等之合金等所構成之金屬陽極,較佳為進行過平坦化處理者。亦可使用具有高電荷傳輸性之聚噻吩衍生物或聚苯胺衍生物。
再者,構成金屬陽極之其他金屬可列舉鈧、鈦、釩、鉻、錳、鐵、鈷、鎳、銅、鋅、鎵、釔、鋯、鈮、鉬、釕、銠、鈀、鎘、銦、鈧、鑭、鈰、鐠、釹、鉕、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,但不限定於此等。
形成電洞傳輸層之材料,可列舉(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-螺聯第、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-9,9-螺聯茀、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-螺聯茀、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-螺聯茀、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-螺聯茀、2,2’-雙(N,N-二苯基胺基)-9,9-螺聯茀、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-螺聯茀、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”-聯三噻吩(BMA-3T)等之寡噻吩類等之電洞傳輸性低分子材料等。
形成發光層之材料,可列舉參(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)-4-(p-苯基酚)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-螺聯茀-2-基)-9,9-螺聯茀、2,7-雙(9,9-螺聯茀-2-基)-9,9-螺聯茀、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-螺聯茀、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-螺聯茀、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”’-聯四苯]-4,4”’-二胺、4,4’-二[10-(萘-1-基)蒽-9-基]聯苯、二苯并{[f,f’]-4,4’,7,7’-四苯基}二茚并[1,2,3-cd:1’,2’,3’-1m]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)聯苯基(CBP)、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-螺聯茀、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-螺聯茀、1,4-雙(三苯基矽烷基)苯、1,3-雙(三苯基矽烷基)苯、雙(4-N,N-二乙胺基-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(三苯基矽烷基)-p-聯三苯、4,4’-二(三苯基矽烷基)聯苯、9-(4-t-丁基苯基)-3,6-雙(三苯基矽烷基)-9H-咔唑、9-(4-t-丁基苯基)-3,6-二-三苯甲基-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-苯并[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-螺聯茀-2-基-二苯基-膦氧化物、9,9’-(5-(三苯基矽烷基)-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-氮雜二苯并[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)二苯并[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雜物共蒸鍍,來形成發光層。
發光性摻雜物,可列舉3-(2-苯并噻唑基)-7-(二乙胺基)香豆素、2,3,6,7-四氫-1,1,7,7-四甲基-1H,5H,11H-10-(2-苯并噻唑基)喹啉啶并(quinolidino)[9,9a,1gh]香豆素、喹吖酮、N,N’-二甲基-喹吖酮、參(2-苯基吡啶)銥(III)(Ir(ppy)3)、雙(2-苯基吡啶)(乙醯丙酮酸)銥(III)(Ir(ppy)2(acac))、參[2-(p-甲苯基)吡啶]銥(III)(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)苯并噻唑]鋅(II)、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-咔唑伸乙
烯基)-1,1’-聯苯、苝、2,5,8,11-四-t-丁基苝、1,4-雙[2-(3-N-乙基咔唑基)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]二苯乙烯、雙[3,5-二氟-2-(2-吡啶基)苯基-(2-羧基吡啶基)]銥(III)、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(III)、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(III)參(1-苯基-3-甲基苯并咪唑啉-2-亞基-C,C2)、mer-銥(III)參(1-苯基-3-甲基苯并咪唑啉-2-亞基-C,C2)、2,7-雙[4-(二苯基胺基)苯乙烯基]-9,9-螺聯茀、6-甲基-2-(4-(9-(4-(6-甲基苯并[d]噻唑-2-基)苯基)蒽-10-基)苯基)苯并[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-四唑酸)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑)((2,4-二氟苄基)二苯基亞膦酸酯)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑酸)(苄基二苯基亞膦酸酯)銥(III)、雙(1-(2,4-二氟苄基)-3-甲基苯并咪唑鎓)(3-(三氟甲基)-5-(2-吡啶基)-
1,2,4-***)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑酸)(4’,6’-二氟苯基吡啶酸)銥(III)、雙(4’,6’-二氟苯基吡啶)(3,5-雙(三氟甲基)-2-(2’-吡啶基)吡咯)銥(III)、雙(4’,6’-二氟苯基吡啶)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-***)銥(III)、(Z)-6-均三甲苯基-N-(6-均三甲苯基喹啉-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-吡喃-4-亞基)丙二腈、4-(二氰基亞甲基)-2-甲基-6-久咯啶基-9-烯基-4H-吡喃、4-(二氰基亞甲基)-2-甲基-6-(1,1,7,7-四甲基久咯啶基-9-烯基)-4H-吡喃、4-(二氰基亞甲基)-2-t-丁基-6-(1,1,7,7-四甲基久咯啶-4-基-乙烯基)-4H-吡喃、參(二苄醯基甲烷)啡啉銪(III)、5,6,11,12-四苯基稠四苯、雙(2-苯并[b]噻吩-2-基-吡啶)(乙醯丙酮酸)銥(III)、參(1-苯基異喹啉)銥(III)、雙(1-苯基異喹啉)(乙醯丙酮酸)銥(III)、雙[1-(9,9-二甲基-9H-茀-2-基)-異喹啉](乙醯丙酮酸)銥(III)、雙[2-(9,9-二甲基-9H-茀-2-基)喹啉](乙醯丙酮酸)銥(III)、參[4,4’-二-t-丁基-(2,2’)-聯吡啶]釕(III)‧雙(六氟磷酸酯)、參(2-苯基喹啉)銥(III)、雙(2-苯基喹啉)(乙醯丙酮酸)銥(III)、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-苯基苯并噻唑)(乙醯丙酮酸)銥(III)、5,10,15,20-四苯基四苯并卟啉鉑、鋨(II)雙(3-三氟甲基-5-(2-吡啶)-吡唑酸)二甲基苯基膦、鋨
(II)雙(3-(三氟甲基)-5-(4-t-丁基吡啶基)-1,2,4-***)二苯基甲基膦、鋨(II)雙(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-***)二甲基苯基膦、鋨(II)雙(3-(三氟甲基)-5-(4-t-丁基吡啶基)-1,2,4-***)二甲基苯基膦、雙[2-(4-n-己基苯基)喹啉](乙醯丙酮酸)銥(III)、參[2-(4-n-己基苯基)喹啉]銥(III)、參[2-苯基-4-甲基喹啉]銥(III)、雙(2-苯基喹啉)(2-(3-甲基苯基)吡啶酸)銥(III)、雙(2-(9,9-二乙基-茀-2-基)-1-苯基-1H-苯并[d]咪唑(imidazolato))(乙醯丙酮酸)銥(III)、雙(2-苯基吡啶)(3-(吡啶-2-基)-2H-苯并吡喃-2-酮酸)銥(III)、雙(2-苯基喹啉)(2,2,6,6-四甲基庚烷-3,5-二酮酸)銥(III)、雙(苯基異喹啉)(2,2,6,6-四甲基庚烷-3,5-二酮酸)銥(III)、銥(III)雙(4-苯基噻吩并[3,2-c]吡啶-N,C2)乙醯丙酮酸、(E)-2-(2-t-丁基-6-(2-(2,6,6-三甲基-2,4,5,6-四氫-1H-吡咯并[3,2,1-ij]喹啉-8-基)乙烯基)-4H-吡喃-4-亞基)丙二腈、雙(3-三氟甲基-5-(1-異喹啉基)吡唑酸)(甲基二苯基膦)釕、雙[(4-n-己基苯基)異喹啉](乙醯丙酮酸)銥(III)、鉑(II)八乙基卟吩、雙(2-甲基二苯并[f,h]喹噁啉)(乙醯丙酮酸)銥(III)、參[(4-n-己基苯基)異喹啉]銥(III)等。
形成電子傳輸層之材料,可列舉8-羥基羥基喹啉-鋰、2,2’,2”-(1,3,5-石油醚甲苯基)-參(1-苯基-1-H-苯并咪唑)、2-(4-聯苯基)5-(4-t-丁基苯基)-1,3,4-
噁二唑、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-羥基喹啉)-4-(苯基酚)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-***、4-(萘-1-基)-3,5-二苯基-4H-1,2,4-***、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-咪唑并[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-羥基苯并[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。
形成電子注入層之材料,可列舉氧化鋰(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、鋰乙醯丙酮酸(Li(acac))、乙酸鋰、安息香酸鋰等。
陰極材料可列舉鋁、鎂-銀合金、鋁-鋰合金、鋰、鈉、鉀、銫等。
又,由本發明之組成物所得到之薄膜為電洞注入層時,本發明之有機EL元件之製作方法的其他之例子,係如以下所述。
前述之EL元件製作方法中,藉由依次形成電洞傳輸層、發光層,以取代進行電洞傳輸層、發光層、電子傳輸層、電子注入層之真空蒸鍍操作,可製作具有由本發明之組成物所形成之電荷傳輸性薄膜的有機EL元件。具體而言,於陽極基板上塗佈本發明之組成物,藉由前述方法製作電洞注入層,於其上依次形成電洞傳輸層、發光層,進而蒸鍍陰極電極,而成為有機EL元件。
所使用之陰極及陽極材料,可使用與前述為相同者,且可進行同樣之洗淨處理、表面處理。
電洞傳輸層及發光層之形成方法,可列舉對電洞傳輸性高分子材料或發光性高分子材料、或於此等中添加有摻雜物之材料添加溶劑進行溶解、或均勻分散,分別於電洞注入層或電洞傳輸層之上進行塗佈後,燒成藉以成膜之方法。
電洞傳輸性高分子材料,可列舉聚[(9,9-二己基茀基-2,7-二基)-co-(N,N’-雙{p-丁基苯基}-1,4-二胺基伸苯基)]、聚[(9,9-二辛基茀基-2,7-二基)-co-(N,N’-雙{p-丁基苯基}-1,1’-聯伸苯基-4,4-二胺)]、聚[(9,9-雙{1’-戊烯-5’-基}茀基-2,7-二基)-co-(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]-以聚倍半矽氧烷封端
(end capped with polysilsesquioxane)、聚[(9,9-二二辛基茀基-2,7-二基)-co-(4,4’-(N-(p-丁基苯基))二苯基胺)]等。
發光性高分子材料,可列舉聚(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-伸苯基伸乙烯基)(MEH-PPV)等之聚伸苯基伸乙烯基衍生物、聚(3-烷基噻吩)(PAT)等之聚噻吩衍生物、聚乙烯基咔唑(PVCz)等。
溶劑可列舉甲苯、二甲苯、氯仿等。溶解或均勻分散法,可列舉攪拌、加熱攪拌、超音波分散等之方法。
塗佈方法並無特殊限定,可列舉噴墨法、噴霧法、浸漬法、旋轉塗佈法、轉印印刷法、輥塗佈法、刷毛塗佈等。再者,塗佈較佳為在氮、氬等之惰性氣體下進行。
燒成方法可列舉在惰性氣體下或真空中,以烘箱或加熱板加熱之方法。
由本發明之組成物所得到之薄膜為電洞注入傳輸層時,本發明之有機EL元件之製作方法的一例,係如以下所述。
於陽極基板上形成電洞注入傳輸層,於該電洞注入傳輸層之上,依序設置發光層、電子傳輸層、電子注入層、陰極。發光層、電子傳輸層及電子注入層之形成方法及具體例子,可列舉與前述為相同者。
形成陽極材料、發光層、發光性摻雜物、電子傳輸層及電子阻擋層之材料、陰極材料,可列舉與前述者為相同者。
再者,亦可於電極及前述各層之間的任意之間,依需要設置空穴阻擋層、電子阻擋層等。例如,作為形成電子阻擋層之材料,可列舉參(苯基吡唑)銥等。
構成於陽極與陰極及此等之間所形成之層的材料,係於具備底部發光構造、頂部發光構造之何者的元件製造上相異,因此係考慮該點來選擇適當材料。
通常,於底部發光構造之元件中,於基板側係使用透明陽極,自基板側取出光,相對於此,於頂部發光構造之元件中,係使用由金屬所成之反射陽極,且由位於與基板相反方向的透明電極(陰極)側取出光。因此,例如提到陽極材料時,製造底部發光構造之元件時係使用ITO等之透明陽極、製造頂部發光構造之元件時係使用Al/Nd等之反射陽極。
本發明之有機EL元件,為了防止特性惡化,亦可遵照特定方法,依需要與捕水劑等一起進行密封。
以下,列舉實施例以更具體說明本發明,但本發明不受下述實施例限定。再者,所使用之裝置係如以下所述。
(1)1H-NMR:日本電子(股)製JNM-ECP300 FT
NMR SYSTEM
(2)MALDI-TOF-MS:Bruker Daltonics公司製、autoflex III smartbeam
(3)基板洗淨:長州產業(股)製 基板洗淨裝置(減壓電漿方式)
(4)組成物(塗料)之塗佈:Mikasa(股)製 旋轉塗佈器MS-A100
(5)膜厚測定:(股)小坂研究所製 微細形狀測定機Surfcorder ET-4000
(6)EL元件之製作:長州產業(股)製 多功能蒸鍍裝置系統C-E2L1G1-N
(7)EL元件之輝度等之測定:(有)Tech World製 I-V-L測定系統
(8)EL元件之壽命測定(半衰期之測定):(股)EHC製 有機EL輝度壽命評估系統PEL-105S
於燒瓶內加入N1-(4-胺基苯基)苯-1,4-二胺
1.00g、3-溴-9-苯基-9H-咔唑8.89g、乙酸鈀112mg、及t-丁氧基鈉3.47g後,將燒瓶內進行氮取代。對其添加甲苯30mL、及預先配製之二-t-丁基(苯基)膦之甲苯溶液2.75mL(濃度81.0g/L),於90℃攪拌6小時。
攪拌結束後,將反應混合物冷卻至室溫,混合冷卻後的反應混合物、甲苯、與離子交換水,進行分液處理。將所得之有機層以硫酸鈉乾燥,進行濃縮。將濃縮液以二氧化矽凝膠進行過濾,對所得之濾液添加活性碳0.2g,於室溫攪拌30分。
之後,以過濾去除活性碳,濃縮濾液。將濃縮液滴下至甲醇及乙酸乙酯之混合溶劑(500mL/500mL)中,將所得之漿料於室溫攪拌一晚,接著過濾漿料回收濾物。乾燥所得之濾物,得到目標之苯胺衍生物1(產量5.88g,產率83%)。
1H-NMR(300MHz,THF-d8)δ[ppm]:8.08(d,J=7.7Hz,2H),7.99(d,J=7.7Hz,8H),7.60-7.64(m,19H),7.42-7.47(m,6H),7.28-7.36(m,19H),7.09-7.21(m,6H),7.00(m,8H)。
MALDI-TOF-MS m/Z found:1404.68([M]+calcd:1404.56)。
將苯胺衍生物1 0.112g、與2,4,6,7-四氰基-1,4,5,8-四
氮雜萘((股)三寶化學研究所製,以下稱為「TCNA」)0.092g,於氮環境下溶解於1,3-二甲基-2-咪唑啉酮(以下稱為「DMI」)5.0g中。對其添加2,3-丁二醇(以下稱為「2,3-BD」)3.0g及二丙二醇單甲基醚(以下稱為「DPM」)2.0g並攪拌,將所得之溶液使用孔徑0.2μm之PTFE製過濾器過濾,得到電荷傳輸性薄膜形成組成物。
將苯胺衍生物1 0.171g、TCNA 0.141g、與磷鎢酸(日本新金屬(股)製,以下稱為「PTA」)0.312g,於氮環境下溶解於DMI 7.5g中。對其添加2,3-BD 4.5g及DPM 3.0g並攪拌,將所得之溶液使用孔徑0.2μm之PTFE製過濾器過濾,得到電荷傳輸性薄膜形成組成物。
將苯胺衍生物1 0.171g、TCNA 0.141g、與PTA 0.312g,於氮環境下溶解於DMI 7.5g中。對其添加2,3-BD 4.5g及DPM 3.0g並攪拌,進一步添加3,3,3-三氟丙基三甲氧基矽烷(信越化學工業(股)製)0.010g及苯基三甲氧基矽烷(信越化學工業(股)製)0.021g並攪拌,將所得之溶液使用孔徑0.2μm之PTFE製過濾器過濾,得到電荷傳輸性薄膜形成組成物。
將實施例1-1中得到之電荷傳輸性薄膜形成組成物,使用旋轉塗佈器塗佈於ITO基板後,於80℃乾燥1分鐘,進一步地,於大氣環境下、150℃燒成10分鐘,於ITO基板上形成30nm之均勻的薄膜。作為ITO基板,係使用於表面上以膜厚150nm圖型化有銦錫氧化物(ITO)的25mm×25mm×0.7t之玻璃基板,使用前藉由O2電漿洗淨裝置(150W、30秒)去除表面上之雜質。
接著,對形成有薄膜之ITO基板,使用蒸鍍裝置(真空度1.0×10-5Pa)使α-NPD以0.2nm/秒成膜30nm。接著,使CBP與Ir(PPy)3進行共蒸鍍。共蒸鍍係以Ir(PPy)3之濃度成為6%的方式來控制蒸鍍速率,層合40nm。接著,依序層合BAlq、氟化鋰及鋁之薄膜,得到有機EL元件。此時,蒸鍍速率,就BAlq及鋁而言為0.2nm/秒、就氟化鋰而言為0.02nm/秒之條件分別進行,膜厚分別為20nm、0.5nm及120nm。
再者,為了防止空氣中之氧、水等之影響所致的特性劣化,有機EL元件係藉由密封基板密封後,評估其特性。密封係由以下順序進行。於氧濃度2ppm以下,露點-85℃以下之氮環境中,使有機EL元件容納於密封基板之間,將密封基板以接著材料((股)MORESCO製、MORESCO MOISTURE CUT WB90US(P))貼合。此時,將捕水劑(Dynic(股)製,HD-071010W-40)與有機EL元件一起
容納於密封基板內。對經貼合之密封基板照射UV光(波長:365nm、照射量:6,000mJ/cm2)後,於80℃退火處理1小時,使接著材料硬化。
除了分別使用實施例1-2~1-3中得到之電荷傳輸性薄膜形成組成物,以取代實施例1-1中得到之電荷傳輸性薄膜形成組成物以外,係以與實施例2-1相同之方法得到元件。
測定使所製作之元件以驅動電流0.7mA發光時的驅動電壓、輝度及發光效率、以及輝度之半衰期(初期輝度5000cd/m2)。結果如表19所示。再者,各元件之發光面尺寸的面積為2mm×2mm。
如表19所示,可知具有由本發明之電荷傳輸性薄膜形成組成物所得到之電荷傳輸性薄膜作為電洞注入層的有機EL元件,輝度特性優良。
又,可知該有機EL元件耐久性亦優良。
Claims (6)
- 一種有機電致發光元件用之電荷傳輸性薄膜形成組成物,其特徵為含有由式(D1)表示之經氰基取代的含氮雜芳香族化合物所成之摻雜物物質、電荷傳輸性物質、與有機溶劑,前述電荷傳輸性物質為下述式(1)表示之苯胺衍生物,且前述摻雜物物質及前述電荷傳輸性物質係溶解於前述有機溶劑,
- 如請求項1之有機電致發光元件用之電荷傳輸性薄膜形成組成物,其中進一步含有有機矽烷化合物。
- 如請求項1之有機電致發光元件用之電荷傳輸性薄膜形成組成物,其中進一步含有雜多酸。
- 如請求項1之有機電致發光元件用之電荷傳輸性薄膜形成組成物,其係有機電致發光元件之電洞注入層、電洞傳輸層或電洞注入傳輸層形成用組成物。
- 一種有機電致發光元件用之電荷傳輸性薄膜,其係使用如請求項1~4中任一項之有機電致發光元件用之電荷傳輸性薄膜形成組成物所製造。
- 一種有機電致發光元件,其係具有如請求項5之有機電致發光元件用之電荷傳輸性薄膜。
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