TW201546047A - 苯胺衍生物及其利用 - Google Patents
苯胺衍生物及其利用 Download PDFInfo
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- TW201546047A TW201546047A TW104108129A TW104108129A TW201546047A TW 201546047 A TW201546047 A TW 201546047A TW 104108129 A TW104108129 A TW 104108129A TW 104108129 A TW104108129 A TW 104108129A TW 201546047 A TW201546047 A TW 201546047A
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- charge transporting
- bis
- carbon atoms
- phenyl
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- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 title abstract description 4
- 239000000126 substance Substances 0.000 claims abstract description 28
- 239000003960 organic solvent Substances 0.000 claims abstract description 20
- -1 halogenated tetracyanoquinodimethane compound Chemical class 0.000 claims description 97
- 125000004432 carbon atom Chemical group C* 0.000 claims description 62
- 239000002966 varnish Substances 0.000 claims description 56
- 150000001448 anilines Chemical class 0.000 claims description 39
- 125000005843 halogen group Chemical group 0.000 claims description 35
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 25
- 239000002019 doping agent Substances 0.000 claims description 24
- 239000000758 substrate Substances 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 239000011964 heteropoly acid Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 150000001491 aromatic compounds Chemical class 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002577 pseudohalo group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 238000005401 electroluminescence Methods 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims 1
- 238000002347 injection Methods 0.000 abstract description 21
- 239000007924 injection Substances 0.000 abstract description 21
- 239000010409 thin film Substances 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 50
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 25
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
- 241000208340 Araliaceae Species 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 15
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- 150000001875 compounds Chemical class 0.000 description 13
- 125000003342 alkenyl group Chemical group 0.000 description 12
- 125000001153 fluoro group Chemical group F* 0.000 description 12
- 229910052731 fluorine Inorganic materials 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 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 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
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- 238000006243 chemical reaction Methods 0.000 description 9
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 8
- 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 8
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
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- 125000001424 substituent group Chemical group 0.000 description 6
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- 150000004057 1,4-benzoquinones Chemical class 0.000 description 5
- 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
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 5
- 229910052787 antimony Inorganic materials 0.000 description 5
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 5
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- 230000005525 hole transport Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
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- 239000002184 metal Substances 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 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- BPEVHDGLPIIAGH-UHFFFAOYSA-N ruthenium(3+) Chemical compound [Ru+3] BPEVHDGLPIIAGH-UHFFFAOYSA-N 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 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 4
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 4
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 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 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
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- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 3
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- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 3
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- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 3
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- XQTIWNLDFPPCIU-UHFFFAOYSA-N cerium(3+) Chemical compound [Ce+3] XQTIWNLDFPPCIU-UHFFFAOYSA-N 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- VBVAVBCYMYWNOU-UHFFFAOYSA-N coumarin 6 Chemical compound C1=CC=C2SC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 VBVAVBCYMYWNOU-UHFFFAOYSA-N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- HQFQTTNMBUPQAY-UHFFFAOYSA-N cyclobutylhydrazine Chemical compound NNC1CCC1 HQFQTTNMBUPQAY-UHFFFAOYSA-N 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
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 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
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-O diphenylphosphanium Chemical compound C=1C=CC=CC=1[PH2+]C1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-O 0.000 description 1
- BUBAPAVHHCZZMA-UHFFFAOYSA-N diphenylphosphoryloxymethylbenzene Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)OCC1=CC=CC=C1 BUBAPAVHHCZZMA-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 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
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 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
- 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
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000011133 lead 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
- COLNWNFTWHPORY-UHFFFAOYSA-M lithium;8-hydroxyquinoline-2-carboxylate Chemical compound [Li+].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 COLNWNFTWHPORY-UHFFFAOYSA-M 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
- 238000011068 loading method Methods 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
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- UJNZOIKQAUQOCN-UHFFFAOYSA-N methyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C)C1=CC=CC=C1 UJNZOIKQAUQOCN-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 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
- NRKQPQQULQMWBV-MBALSZOMSA-N n,n-diphenyl-4-[(e)-2-[6-[(e)-2-[4-(n-phenylanilino)phenyl]ethenyl]naphthalen-2-yl]ethenyl]aniline 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=C2\C=C\C(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 NRKQPQQULQMWBV-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
- OKPMSRGLGBBULD-UHFFFAOYSA-N n,n-diphenyl-9,9'-spirobi[fluorene]-1-amine Chemical compound C1=CC=CC=C1N(C=1C=2C3(C4=CC=CC=C4C4=CC=CC=C43)C3=CC=CC=C3C=2C=CC=1)C1=CC=CC=C1 OKPMSRGLGBBULD-UHFFFAOYSA-N 0.000 description 1
- ZJFKMIYGRJGWIB-UHFFFAOYSA-N n-[3-methyl-4-[2-methyl-4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound CC1=CC(N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)=CC=C1C(C(=C1)C)=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 ZJFKMIYGRJGWIB-UHFFFAOYSA-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
- LBFXFIPIIMAZPK-UHFFFAOYSA-N n-[4-[4-(n-phenanthren-9-ylanilino)phenyl]phenyl]-n-phenylphenanthren-9-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C2=CC=CC=C2C=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C3=CC=CC=C3C=2)C=C1 LBFXFIPIIMAZPK-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 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
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- GKROKAVBUIADBS-UHFFFAOYSA-N phenanthrene-2-carbaldehyde Chemical group C1=CC=C2C3=CC=C(C=O)C=C3C=CC2=C1 GKROKAVBUIADBS-UHFFFAOYSA-N 0.000 description 1
- 150000004031 phenylhydrazines Chemical class 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review 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
- 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
- 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
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- 229930192474 thiophene Natural products 0.000 description 1
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 150000003672 ureas Chemical class 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
- 239000008096 xylene Substances 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
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- 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
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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Abstract
本發明為例如由下述式所表示般的苯胺衍生物,對有機溶劑的溶解性良好,而且在將含有該等作為電荷輸送性物質的薄膜適用於正電洞注入層的情況下,可得到輝度特性優異的有機EL元件。
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Description
本發明關於一種苯胺衍生物及其利用。
有機電致發光(以下稱為有機EL)元件可採用由有機化合物所構成之電荷輸送性薄膜作為發光層或電荷注入層。尤其正電洞注入層是負責陽極與正電洞輸送層或發光層的電荷的授受,為了達成有機EL元件的低電壓驅動及高輝度而發揮重要的機能。
正電洞注入層的形成方法,大致區別為蒸鍍法所代表的乾式程序,以及旋轉塗佈法所代表的濕式程序,若比較這些程序,則濕式程序較能夠有效率地製造出大面積且平坦性高的薄膜。所以,有機EL顯示器往大面積化發展的現在,需要能夠以濕式程序形成的正電洞注入層。
鑑於這樣的狀況,本發明人等開發出可適用於各種濕式程序,而且在適用於有機EL元件的正電洞注入層的情況,可產生能夠實現優異的EL元件特性的薄膜的的電荷輸送性材料、或對於其所使用的有機溶劑的溶解性良好的化合物(參考例如專利文獻1~4)。
[專利文獻1]國際公開第2008/067276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
本發明與目前為止開發出的上述專利文獻技術同樣地,目的為提供一種苯胺衍生物,表現出對有機溶劑良好的溶解性,而且在薄膜化並適用於正電洞注入層的情況,可實現具有優異的輝度特性的有機EL元件。
本發明人等為了達成上述目的潛心反覆檢討,結果發現,不採用醌二亞胺構造的既定苯胺衍生物,具有對有機溶劑優異的溶解性,由使其溶於有機溶劑所調製出的清漆可得到發揮出高電荷輸送性的薄膜、及在將該薄膜適用於有機EL元件的正電洞注入層的情況,可得到高輝度的元件,而完成了本發明。
亦即,本發明提供:
1.一種苯胺衍生物,其特徵為:由式(1)所表示,
[式中,X表示S、O、CH2、或NCH3,Ph1互相獨立,表示由式(P1)所表示之基,
(式中,R1~R4互相獨立,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之芳香基或碳數2~20之雜芳香基)
Ar1互相獨立,表示由式(A1)~(A14)所表示之任一基,
m及n互相獨立,表示0~5之整數]。
2.如1之苯胺衍生物,其中前述R1~R4全部為氫原子,
3.如1或2之苯胺衍生物,其中前述Ar1互相獨立,而為由式(A1)~(A12)所表示之任一基,
4.如3之苯胺衍生物,其中前述Ar1互相獨立,而為由式(A1)~(A3)、(A5)~(A7)、及(A10)~(A12)所表示之任一基,
5.如1~4中任一者之苯胺衍生物,其中前述Ar1為相同之基,
6.一種電荷輸送性物質,其係由如1~5中任一者之苯胺衍生物所構成,
7.一種電荷輸送性材料,其係含有如6之電荷輸送性物質,
8.一種電荷輸送性清漆,其係含有如6之電荷輸送性物質與有機溶劑,
9.如8之電荷輸送性清漆,其中進一步含有摻雜物質,
10.如9之電荷輸送性清漆,其中前述摻雜物質含有鹵代四氰基醌二甲烷化合物,
11.如10之電荷輸送性清漆,其中前述摻雜物質進一步含有異聚酸,
12.一種電荷輸送性薄膜,其係使用如8~11中任一者之電荷輸送性清漆所製作,
13.一種電子裝置,其係具有如12之電荷輸送性薄膜,
14.一種有機電致發光元件,其係具有如12之電荷輸送性薄膜,
15.一種電荷輸送性薄膜之製造方法,其特徵為:將如8~11中任一者之電荷輸送性清漆塗佈於基材上,並使溶劑蒸發,
16.一種苯胺衍生物的製造方法,其特徵為:使式(2)所表示之胺化合物在觸媒存在下與式(3)所表示之芳香基化合物反應,
(式中,Ph1、X、m及n表示與前述相同意思)
【化5】Ar1-Z (3)
(式中,Z表示鹵素原子或假鹵素基,Ar1表示與前述相同意思)。
本發明之苯胺衍生物容易溶於有機溶劑中,使其與摻雜物一起溶於有機溶劑,可輕易地調製出電荷輸送性清漆。
由本發明之電荷輸送性清漆所製作出的薄膜表現出高電荷輸送性,因此適合使用作為以有機EL元件為首的電子裝置用的薄膜。尤其藉由將此薄膜適用於有機EL元件的正電洞注入層,可得到輝度特性優異的有機EL元件。
另外,本發明之電荷輸送性清漆,即使在使用旋轉塗佈法或狹縫塗佈法等、可大面積成膜的各種濕式程序的情況,也能夠以良好的再現性製造出電荷輸送性優異的薄膜,因此也能夠充分對應於近年來的有機EL元件領域的發展。
以下對本發明進一步詳細說明。
本發明所關連的苯胺衍生物是由式(1)所表示。
式中,X表示S、O、CH2、NCH3,而宜為S、O、NCH3。
Ph1互相獨立,表示由式(P1)所表示之基。
此處,R1~R4互相獨立,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之芳香基或碳數2~20之雜芳香基。
鹵素原子可列舉氟原子、氯原子、溴原子、碘原子等。
碳數1~20之烷基可為直鏈狀、支鏈狀、環狀之任一者,可列舉例如甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁基、第三丁基、正戊基、正己基、正庚基、正辛基、正壬基、正癸基等的碳數1~20之直鏈或支
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、雙環癸基等的碳數3~20之環狀烷基等。
碳數2~20之烯基的具體例,可列舉乙烯基、1-正丙烯基、2-正丙烯基、1-甲基乙烯基、1-正丁烯基、2-正丁烯基、3-正丁烯基、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、1-正戊烯基、1-正癸烯基、1-正二十碳烯基等。
碳數2~20之炔基的具體例,可列舉乙炔基、1-正丙炔基、2-正丙炔基、1-正丁炔基、2-正丁炔基、3-正丁炔基、1-甲基-2-丙炔基、1-正戊炔基、2-正戊炔基、3-正戊炔基、4-正戊炔基、1-甲基正丁炔基、2-甲基正丁炔基、3-甲基正丁炔基、1,1-二甲基正丙炔基、1-正己炔基、1-正癸炔基、1-正十五碳炔基、1-正二十碳炔基等。
碳數6~20之芳香基的具體例,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之雜芳香基的具體例,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、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。
該等之中,R1~R4係以氫原子、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之芳香基、可經鹵素原子取代之碳數2~20之雜芳香基為佳,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為較佳,氫原子、氟原子為更佳,氫原子為最適。
上述式(1)中的Ar1互相獨立,表示由式(A1)~(A14)所表示之任一基。
從提升化合物對有機溶劑的溶解性,或所得到的薄膜之電荷輸送性的觀點看來,該等之中,以由式(A1)~(A12)所表示之任一基為佳,由式(A1)~(A3)、(A5)~(A7)、及(A10)~(A12)所表示之任一基為較佳,式(A1)、(A5)、及(A10)~(A12)所表示之任一基為更佳,由式(A1)及(A5)所表示之任一基為再更佳。
上述式(1)中的m及n互相獨立,表示0~5之整數,從提高化合物對有機溶劑的溶解性的觀點看來,以0~3為佳,以0或1為較佳,同時為0或1為更佳,此外,從原料化合物的取得容易性的觀點看來,同時為0為最適。
上述式(1)之中,Ar1宜全部為相同之基,Ph1宜全部為相同之基。
此外,在本發明中,上述烷基、烯基及炔基之碳數宜為10以下,較佳為6以下,更佳為4以下。
另外,芳香基及雜芳香基之碳數宜為14以下,較佳為10以下,更佳為6以下。
本發明之由式(1)所表示之苯胺衍生物,可
藉由使由式(2)所表示之胺化合物與由式(3)所表示之芳香基化合物在觸媒存在下反應來製造。
(式中,Z表示鹵素原子或假鹵素基,X、Ar1、Ph1、m及n表示與前述相同意思)。
鹵素原子可列舉與上述同樣的原子。
假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的(氟)烷基磺醯氧基;苯磺醯氧基、甲苯磺醯氧基等的芳香族磺醯氧基等。
關於由式(2)所表示之胺化合物與由式(3)所表示之芳香基化合物的裝填比,相對於胺化合物的全NH基的物質量,可將芳香基化合物定在當量以上,而以1~1.2當量左右為適合。
上述反應所使用的觸媒可列舉例如氯化銅、溴化銅、碘化銅等的銅觸媒;Pd(PPh3)4(肆(三苯膦)鈀)、Pd(PPh3)2Cl2(雙(三苯膦)二氯鈀)、Pd(dba)2(雙(亞苄基丙酮)鈀)、Pd2(dba)3(參(亞苄基丙酮)二鈀)、Pd(P-t-Bu3)2(雙(三第三丁基膦)鈀)等的鈀觸媒等。這些觸媒可單獨使用,或可組合兩種以上使用。
另外,這些觸媒亦可與周知的適當配位子一起使用。
觸媒的使用量可定在相對於由式(3)所表示之芳香基化合物1mol為0.2mol左右,以0.15mol左右為適合。
另外,在使用配位子的情況下,其使用量可定在相對於所使用的金屬錯合物為0.1~5當量,以1~2當量為適合。
上述各反應可在溶劑中進行。在使用溶劑的情況下,只要不會對反應造成不良影響,則其種類並無特別限制。具體例可列舉脂肪族烴類(戊烷、正己烷、正辛烷、正癸烷、十氫萘等)、鹵素化脂肪族烴類(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、鄰二甲苯、間二甲苯、對二甲苯、均三甲苯等)、鹵素化芳香族烴類(氯苯、溴苯、鄰二氯苯、間二氯苯、對二氯苯等)、醚類(二***、二異丙基醚、第三丁基甲醚、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、二正丁基酮、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-甲基吡咯烷酮、γ-丁內酯等)、尿素類(N,N-二甲基咪唑啶酮(imidazolidinone)、四甲基尿素等)、亞碸類(二甲亞碸、環丁碸等)、腈類(乙腈、丙腈、丁腈等)等,這些溶劑可單獨使用,或可混合兩種以上使用。
反應溫度只要適當地設定在所使用的溶劑的
熔點至沸點的範圍即可,而尤其以0~200℃左右為佳,20~150℃為較佳。
在反應結束後,依據常法進實施後處理,可得到目標之苯胺衍生物。
以下列舉由式(1)所表示之苯胺衍生物的具體例,然而並不受這些例子所限定。
本發明之電荷輸送性清漆含有由式(1)所表示之苯胺衍生物所構成的電荷輸送性物質與有機溶劑,亦可因應所得到的薄膜的用途,並為了提升其電荷輸送能等目的而含有摻雜物質。
摻雜物質只要可溶於清漆所使用的至少一種溶劑,則並不受特別限定,無機系摻雜物質、有機系摻雜物質之任一者皆可使用。
尤其無機系摻雜物質係以異聚酸為佳。
異聚酸,代表性地由式(D1)所表示的Keggin型或由式(D2)所表示的Dawson型的化學構造所表示,是指具有雜原子位於分子的中心的構造,釩(V)、鉬
(Mo)、鎢(W)等的含氧酸的同素聚合酸與異種元素的含氧酸縮合而成的聚酸。這種異種元素的含氧酸,主要可列舉矽(Si)、磷(P)、砷(As)的含氧酸。
異聚酸的具體例,可列舉磷鉬酸、矽鉬酸、磷鎢酸、矽鎢酸、磷鎢鉬酸等,該等可單獨使用或可組合兩種以上使用。此外,本發明所使用的異聚酸能夠以市售品的方式取得,另外還可藉由周知的方法來合成。
尤其在使用一種異聚酸的情況下,該一種異聚酸係以磷鎢酸或磷鉬酸為佳,磷鎢酸為最適。另外,在使用兩種以上的異聚酸的情況下,該兩種以上的異聚酸的其中一種為磷鎢酸或磷鉬酸為佳,磷鎢酸為較佳。
此外,異聚酸無論在元素分析等的定量分析時一般式所表示的構造中的元素數目多或少,只要能夠以市售品的方式取得,或依據周知的合成方法適當地合成,即可在本發明中使用。
亦即,例如一般來說磷鎢酸是由化學式H3(PW12O40).nH2O來表示,磷鉬酸是由化學式H3(PMo12O40).nH2O來表示,而無論在定量分析時此式中的P(磷)、O(氧)或W(鎢)或Mo(鉬)的數量多或
少,只要能夠以市售品的方式取得,或依據周知的合成方法適當地合成,即可在本發明中使用。此情況下,本發明所規定的異聚酸的質量,並非意指合成物或市售品中純粹的磷鎢酸質量(磷鎢酸含量),而是指在能夠以市售品的方式取得的形態及可藉由周知的合成法分離的形態中,在含有水合水或其他雜質等的狀態下的總質量。
本發明之電荷輸送性清漆所含的異聚酸,以相對於由本發明之苯胺衍生物所構成的電荷輸送性物質的質量比而計,可設定在0.01~50左右,而宜為0.1~10左右,較佳為1.0~5.0左右。
另一方面,有機系摻雜物質尤其以四氰基醌二甲烷衍生物或苯醌衍生物為佳。
四氰基醌二甲烷衍生物的具體例,可列舉7,7,8,8-四氰基醌二甲烷(TCNQ)、或由式(4)所表示之鹵代四氰基醌二甲烷等。
另外,苯醌衍生物的具體例,可列舉四氟-1,4-苯醌(F4BQ)、四氯-1,4-苯醌(chloranil)、四溴-1,4-苯醌、2,3-二氯-5,6-二氰基-1,4-苯醌(DDQ)等。
式中,R5~R8互相獨立,表示氫原子或鹵素
原子,而至少一個為鹵素原子,至少兩個為鹵素原子為佳,至少3個為鹵素原子為較佳,全部為鹵素原子為最佳。
鹵素原子可列舉係與上述相同的原子,而以氟原子或氯原子為佳,氟原子為較佳。
鹵代四氰基醌二甲烷化合物的具體例,可列舉2-氟-7,7,8,8-四氰基醌二甲烷、2-氯-7,7,8,8-四氰基醌二甲烷、2,5-二氟-7,7,8,8-四氰基醌二甲烷、2,5-二氯-7,7,8,8-四氰基醌二甲烷、2,3,5,6-四氯-7,7,8,8-四氰基醌二甲烷、2,3,5,6-四氟-7,7,8,8-四氰基醌二甲烷(F4TCNQ)等,而在本發明中,F4TCNQ為最適。
本發明之電荷輸送性清漆中的四氰基醌二甲烷衍生物及苯醌衍生物的含量,相對於本發明之苯胺衍生物,宜為0.0001~50當量,較佳為0.001~20當量,更佳為0.01~10當量。
在本發明中,若考慮到以良好的再現性得到高電荷輸送性的薄膜、摻雜物質的取得容易性等,則以含有鹵代四氰基醌二甲烷及苯醌衍生物的至少一種作為摻雜物質為佳,含有F4TCNQ及DDQ的至少一種為較佳。
另外,在將所得到的薄膜使用作為有機EL元件的正電洞注入層的情況下,若考慮到以良好的再現性得到高壽命的元件、摻雜物質的取得容易性等,則以含有鹵代四氰基醌二甲烷及苯醌衍生物的至少一種與異聚酸作為摻雜物質為佳,含有鹵代四氰基醌二甲烷及苯醌衍生物的至少一
種與磷鎢酸及磷鉬酸的至少一種為較佳,含有F4TCNQ及DDQ的至少一種與磷鎢酸為更佳。
此外,在將所得到的薄膜使用作為有機EL元件的正電洞注入層的情況下,若考慮到以良好的再現性得到高壽命的元件,則本發明之電荷輸送性清漆係以含有有機矽烷化合物為佳。
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,該等可單獨使用或可組合兩種以上使用。
尤其有機矽烷化合物係以二烷氧基矽烷化合物或三烷氧基矽烷化合物為佳,三烷氧基矽烷化合物為較佳。
這些烷氧基矽烷化合物,可列舉例如由式(5)~(7)所表示的物質。
Si(OR)4 (5)
SiR'(OR)3 (6)
Si(R')2(OR)2 (7)
式中,R互相獨立,表示可經Z1取代之碳數1~20之烷基、可經Z1取代之碳數2~20之烯基、可經Z1取代之碳數2~20之炔基、可經Z2取代之碳數6~20之芳香基、或可經Z2取代之碳數2~20之雜芳香基,R’互相獨立,表示可經Z3取代之碳數1~20之烷基、可經Z3取代之碳數2~20之烯基、可經Z3取代之碳數2~20之炔基、可經Z4取代之碳數6~20之芳香基、或可經Z4取代之碳數2~20之雜芳香基。
Z1表示鹵素原子、可經Z5取代之碳數6~20
之芳香基、或可經Z5取代之碳數2~20之雜芳香基,Z2表示鹵素原子、可經Z5取代之碳數1~20之烷基、可經Z5取代之碳數2~20之烯基、或可經Z5取代之碳數2~20之炔基。
Z3表示鹵素原子、可經Z5取代之碳數6~20之芳香基、可經Z5取代之碳數2~20之雜芳香基、環氧環己基、縮水甘油氧基(glycidoxy)、甲基丙烯醯氧基、丙烯醯氧基、脲基(-NHCONH2)、硫醇基、異氰酸基(-NCO)、胺基、-NHY1基、或-NY2Y3基,Z4表示鹵素原子、可經Z5取代之碳數1~20之烷基、可經Z5取代之碳數2~20之烯基、可經Z5取代之碳數2~20之炔基、環氧環己基、縮水甘油氧基(glycidoxy)、甲基丙烯醯氧基、丙烯醯氧基、脲基(-NHCONH2)、硫醇基、異氰酸基(-NCO)、胺基、-NHY1基、或-NY2Y3基,Y1~Y3互相獨立,表示可經Z5取代之碳數1~20之烷基、可經Z5取代之碳數2~20之烯基、可經Z5取代之碳數2~20之炔基、可經Z5取代之碳數6~20之芳香基、或可經Z5取代之碳數2~20之雜芳香基。
Z5表示鹵素原子、胺基、硝基、氰基或硫醇基。
式(5)~(7)中的鹵素原子、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之芳香基、及碳數2~20之雜芳香基可列舉與上述同樣的基團。
在R及R’之中,烷基、烯基及炔基的碳數宜為10以
下,較佳為6以下,更佳為4以下。
另外,芳香基及雜芳香基的碳數宜為14以下,較佳為10以下,更佳為6以下。
R係以可經Z1取代之碳數1~20之烷基或碳數2~20之烯基、或可經Z2取代之碳數6~20之芳香基為佳,可經Z1取代之碳數1~6之烷基或碳數2~6之烯基、或可經Z2取代之苯基為較佳,可經Z2取代之碳數1~4之烷基或可經Z2取代之苯基為更佳,可經Z1取代之甲基或乙基為更佳。
另外,R’係以可經Z3取代之碳數1~20之烷基或可經Z4取代之碳數6~20之芳香基為佳,可經Z3取代之碳數1~10之烷基或可經Z4取代之碳數6~14之芳香基為較佳,可經Z3取代之碳數1~6之烷基、或可經Z4取代之碳數6~10之芳香基為更佳,可經Z3取代之碳數1~4之烷基或可經Z4取代之苯基為更佳。
此外,多個R可全部相同或相異,多個R’亦可全部相同或相異。
Z1係以鹵素原子或可經Z5取代之碳數6~20之芳香基為佳,氟原子或可經Z5取代之苯基為較佳,不存在(亦即未經取代)為最適。
另外,Z2係以鹵素原子或可經Z5取代之碳數6~20之烷基為佳,氟原子或可經Z5取代之碳數1~10之烷基為較佳,不存在(亦即未經取代)為最適。
另一方面,Z3係以鹵素原子、可經Z5取代之
苯基、可經Z5取代之呋喃基、環氧環己基、縮水甘油氧基(glycidoxy)、甲基丙烯醯氧基、丙烯醯氧基、脲基、硫醇基、異氰酸基、胺基、可經Z5取代之苯胺基、或可經Z5取代之二苯胺基為佳,鹵素原子為較佳,氟原子、或不存在(亦即未經取代)為更佳。
另外,Z4係以鹵素原子、可經Z5取代之碳數1~20之烷基、可經Z5取代之呋喃基、環氧環己基、縮水甘油氧基(glycidoxy)、甲基丙烯醯氧基、丙烯醯氧基、脲基、硫醇基、異氰酸基、胺基、可經Z5取代之苯胺基、或可經Z5取代之二苯胺基為佳,鹵素原子為較佳,氟原子、或不存在(亦即未經取代)為更佳。
而且,Z5係以鹵素原子為佳,氟原子或不存在(亦即未經取代)為較佳。
以下列舉本發明所能夠使用的有機矽烷化合物的具體例,然而並不受這些例子限定。
二烷氧基矽烷化合物的具體例,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-縮水甘油氧基(glycidoxy)丙基甲基二甲氧基矽烷、3-縮水甘油氧基(glycidoxy)丙基甲基二乙氧基矽烷、3-(3,4-環氧環己基)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-巰丙基甲基二甲氧基矽烷、γ-胺丙基甲基二乙氧基矽烷、N-(2-胺乙基)胺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的具體例,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、3-胺丙基三甲氧基矽烷、3-胺丙基三乙氧基矽烷、3-縮水甘油氧基(glycidoxy)丙基三甲氧基矽烷、3-縮水甘油氧基(glycidoxy)丙基三乙氧基矽烷、3-甲基丙烯醯氧基丙基三甲氧基矽烷、3-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、(三乙氧基甲矽烷基)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-(三乙氧基甲
矽烷基)呋喃等。
四烷氧基矽烷化合物的具體例,可列舉四乙氧基矽烷、四甲氧基矽烷、四丙氧基矽烷等。
該等之中,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、五氟苯基三甲氧基矽烷、五氟苯基三乙氧基矽烷為佳。
在本發明之電荷輸送性清漆含有有機矽烷化合物的情況下,其含量相對於電荷輸送性物質(在含有摻雜物質的情況,為電荷輸送性物質及摻雜物質)的總質量通常為0.1~50質量%左右,若考慮到抑制所得到的薄膜的電荷輸送性的降低,以及提高正電洞注入積層於上述陰極側而且與正電洞注入層相接的層的能力,則宜為0.5~40質量%左右,較佳為0.8~30質量%左右,更佳為1~20質量%左右。
此外,本發明之電荷輸送性清漆除了可使用由上述苯胺衍生物所構成之電荷輸送性物質之外,還可使用周知的其他電荷輸送性物質。
調製電荷輸送性清漆時所使用的有機溶劑,可採用能夠使電荷輸送性物質及摻雜物質良好地溶解的高溶解性溶劑。
這種高溶解性溶劑,可列舉例如環己酮、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N,N-二甲基異丁基醯胺、N-甲基吡咯烷酮、1,3-二甲基-2-咪唑啶酮、二乙二醇單甲醚
等的有機溶劑,而並不受該等所限定。這些溶劑可單獨使用一種,或混合兩種以上使用,其使用量可定為相對於清漆所使用的溶劑全體為5~100質量%。
此外,電荷輸送性物質及摻雜物質任一者皆以在上述溶劑中完全溶解或成為均勻分散的狀態為佳,以完全溶解為較佳。
另外,在本發明中,藉由使清漆中含有至少一種在25℃下黏度為10~200mPa.s,尤其35~150mPa.s,在常壓(大氣壓)下沸點為50~300℃,尤其150~250℃的高黏度有機溶劑,容易調整清漆的黏度,其結果,能夠以良好的再現性產生平坦性高的薄膜,而且可因應所使用的塗佈方法來調製清漆。
高黏度有機溶劑可列舉例如環己醇、乙二醇、乙二醇二縮水甘油醚、1,3-辛二醇、二乙二醇、二丙二醇、三乙二醇、三丙二醇、1,3-丁二醇、2,3-丁二醇、1,4-丁二醇、丙二醇、己二醇等,而並不受該等所限定。這些溶劑可單獨使用,或可混合兩種以上使用。
高黏度有機溶劑相對於本發明之清漆所使用的溶劑全體的添加比例,係以在固體不會析出的範圍內為佳,只要沒有固體析出,添加比例係以5~80質量%為佳。
此外,為了提升對基板的潤濕性、調整溶劑表面張力、調整極性、調整沸點等目的,亦能夠以相對於清漆所使用的溶劑全體為1~90質量%,宜為1~50質量%的比例混合其他溶劑。
這種溶劑可列舉例如丙二醇單甲醚、乙二醇單丁醚、二乙二醇二***、二乙二醇二甲醚、二乙二醇單***醋酸酯、二乙二醇單丁醚醋酸酯、二丙二醇單甲醚、丙二醇單甲醚醋酸酯、二乙二醇單***、二丙酮醇、γ-丁內酯、乳酸乙酯、醋酸正己酯等,然而並不受該等所限定。這些溶劑可單獨使用一種或混合兩種以上使用。
本發明之清漆的黏度因應所製作出的薄膜厚度等或固體成分濃度適當地設定,而通常在25℃下為1~50mPa.s。
另外,本發明中之電荷輸送性清漆之固體成分濃度需考慮清漆的黏度及表面張力等或所製作的薄膜厚度等適當地設定,通常為0.1~10.0質量%左右,若考慮到提升清漆的塗佈性,則宜為0.5~5.0質量%左右,較佳為1.0~3.0質量%左右。
電荷輸送性清漆的調製法並未受到特別限定,可列舉例如使本發明之苯胺衍生物溶於高溶解性溶劑,並於其中加入高黏度有機溶劑的手段、或將高溶解性溶劑與高黏度有機溶劑混合,並使本發明之苯胺衍生物溶於其中的手段。
在本發明中,從以良好的再現性得到平坦性較高的薄膜的觀點看來,電荷輸送性清漆希望是使電荷輸送性物質、摻雜物質等溶於有機溶劑,然後使用次微米級的過濾器等加以過濾。
藉由將以上所說明的電荷輸送性清漆塗佈在
基材上,並且燒成,可在基材上形成電荷輸送性薄膜。
清漆的塗佈方法並未受到特別限定,可列舉浸漬法、旋轉塗佈法、轉印印刷法、輥式塗佈法、刷毛塗佈、噴墨法、噴霧法、狹縫塗佈法等,宜因應塗佈方法來調節清漆的黏度及表面張力。
另外,在使用本發明之清漆的情況下,燒成氣體環境也並未受到特別限定,不僅是大氣環境,在氮氣等的惰性氣體或真空中,也能夠得到具有均勻成膜面及電荷輸送性的薄膜,若考慮到以良好的再現性得到高電荷輸送性薄膜,則宜為大氣環境。
燒成溫度是考慮到所得到的薄膜的用途,對所得到的薄膜賦予的電荷輸送性的程度、溶劑的種類或沸點等而適當地設定在100~260℃左右的範圍內,在將所得到的薄膜使用作為有機EL元件的正電洞注入層的情況下,以140~250℃左右為佳,145~240℃左右為較佳。
此外,在燒成時,為了表現出較高的均勻成膜性或在基材上進行反應之目的,產生兩階段以上的溫度變化亦可,加熱只要使用例如熱板或烘箱等適當的機器進行即可。
電荷輸送性薄膜的膜厚並未受到特別限定,在有機EL元件內使用作為正電洞注入層的情況下,以5~200nm為佳。改變膜厚的方法已知有改變清漆中的固體成分濃度,或改變塗佈時基板上的溶液量等的方法。
本發明之電荷輸送性薄膜適合使用作為有機
EL元件之中的正電洞注入層,亦可使用作為正電洞注入輸送層等的電荷輸送性機能層。
在使用本發明之電荷輸送性清漆製作OLED元件的情況,使用材料、或製作方法可列舉如下,然而並不受該等所限定。
所使用的電極基板宜預先利用洗潔劑、醇類、純水等進行液體洗淨使其淨化,例如陽極基板宜在開始使用之前進行UV臭氧處理、氧-電漿處理等的表面處理。但是在陽極材料以有機物為主成分的情況下,亦可不進行表面處理。
具有由本發明之電荷輸送性清漆所得到的薄膜所構成之正電洞注入層的OLED元件之製作方法的例子如以下所述。
藉由上述方法,在陽極基板上塗佈本發明之電荷輸送性清漆,並且燒成,在電極上製作出正電洞注入層。將其導入真空蒸鍍裝置內,依序蒸鍍正電洞輸送層、發光層、電子輸送層、電子輸送層/電洞(hole)阻擋層、陰極金屬,而製成OLED元件。此外,還可因應必要,在發光層與正電洞輸送層之間設置電子阻擋層。
陽極材料可列舉由氧化銦錫(ITO)、氧化銦鋅(IZO)所代表的透明電極、或鋁所代表的金屬或該等的合金等所構成的金屬陽極,以進行平坦化處理為佳。亦可使用具有高電荷輸送性的聚噻吩衍生物或聚苯胺衍生物。
此外,構成金屬陽極的其他金屬,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、鉅、釤、銪、釓、鋱、鏑、鈥、鉺、銩、鐿、鉿、鉈、鎢、錸、鋨、銥、鉑、金、鈦、鉛、鉍或該等的合金等,然而並不受該等所限定。
形成正電洞輸送層的材料可列舉(三苯胺)二聚物衍生物、[(三苯胺)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-螺雙茀、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-9,9-螺雙茀、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-二苯胺基)-9,9-螺雙茀、9,9-雙[4-(N,N-雙-聯苯-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-苯胺基)-苯基]-9H-茀、2,2’,7,7’-肆[N-萘基(苯基)-胺基]-9,9-螺雙茀、N,N’-雙(菲-9-基)-N,N’-雙(苯基)-聯苯胺、2,2’-雙[N,N-雙(聯苯-4-基)胺基]-9,9-螺雙茀、2,2’-雙(N,N-二苯胺基)-9,9-螺雙茀、二-[4-(N,N-二(對甲苯基)胺
基)-苯基]環己烷、2,2’,7,7’-四(N,N-二(對甲苯基))胺基-9,9-螺雙茀、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(間甲苯基)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(對甲苯基)胺基)苯基)聯苯、4,4’,4”-參[3-甲基苯基(苯基)胺基]三苯胺(m-MTDATA)、4,4’,4”-參[1-萘基(苯基)胺基]三苯胺(1-TNATA)等的三芳香基胺類、5,5”-雙-{4-[雙(4-甲基苯基)胺基]苯基}-2,2’:5’,2”-聯三噻吩(BMA-3T)等的寡噻吩類等。
形成發光層的材料,可列舉參(8-喹啉根)鋁(III)(Alq3)、雙(8-喹啉根)鋅(II)(Znq2)、雙(2-甲基-8-喹啉根)(對苯基苯酚根)鋁(III)(BAlq)、4,4’-雙(2,2-二苯基乙烯基)聯苯、9,10-二(萘-2-基)蒽、2-第三丁基-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-螺雙茀-2-基)-9,9-螺雙茀、2,7-雙(9,9-螺雙茀-2-基)-9,9-螺雙茀、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-螺雙茀、1,3,5-參(芘-1-基)苯、9,9-雙[4-(芘基)苯基]-9H-茀、2,2’-雙(9,10-二苯
基蒽)、2,7-二芘基-9,9-螺雙茀、1,4-二(芘-1-基)苯、1,3-二(芘-1-基)苯、6,13-二(聯苯-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-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]-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)三苯胺、4,4’-雙(咔唑-9-基)聯苯(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-螺雙茀、2,7-雙(咔唑-9-基)-9,9-二(對甲苯基)茀、9,9-雙[4-(咔唑-9-基)-苯基]茀、2,7-雙(咔唑-9-基)-9,9-螺雙茀、1,4-雙(三苯基甲矽烷基)苯、1,3-雙(三苯基甲矽烷基)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(三苯基甲矽烷基)-對聯三苯、4,4’-二(三苯基甲矽烷基)聯苯、9-(4-第三丁基苯基)-3,6-雙(三苯基甲矽烷基)-9H-咔唑、9-(4-第三丁基苯基)-3,6-二-三苯甲基-9H-咔唑、9-(4-第三丁基苯基)-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-螺雙茀-2-基-二苯基氧化膦、9,9’-(5-(三苯基甲矽烷基)-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(對甲苯基)-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進行共蒸鍍而形成發光層。
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)喹嗪并[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-(對甲苯基)吡啶]銥(III)(Ir(mppy)3)、9,10-雙[N,N-二(對甲苯基)胺基]蒽、9,10-雙[苯基(間甲苯基)胺基]蒽、雙[2-(2-羥苯基)苯并噻唑根]鋅(II)、N10,N10,N10’,N10’-四(對甲苯
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-第三丁基苝、1,4-雙[2-(3-N-乙基咔唑基)乙烯基]苯、4,4’-雙[4-(二-對甲苯胺基)苯乙烯基]聯苯、4-(二-對甲苯胺基)-4’-[(二-對甲苯胺基)苯乙烯基]茋、雙(3,5-二氟)-2-(2-吡啶基)苯基-(2-羧基吡啶基)銥(III)、4,4’-雙[4-(二苯胺基)苯乙烯基]聯苯、雙(2,4-二氟苯基吡啶根)肆(1-吡唑基)硼酸銥(III)、N,N’-雙(萘-2-基)-N,N’-雙(苯基)-參(9,9-二甲基亞芴基)、2,7-雙{2-[苯基(間甲苯基)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-(二苯胺基)苯乙烯基]-9,9-螺雙茀、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-(二苯胺基)苯乙烯基)-N,N-二苯基萘-2-胺、雙(2,4-二氟苯基吡啶根)(5-(吡啶-2-基)-1H-四唑根)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑)((2,4-二氟苄基)二苯基次磷酸根)銥(III)、雙(3-
三氟甲基-5-(2-吡啶基)吡唑根)(苄基二苯基次磷酸根)銥(III)、雙(1-(2,4-二氟苄基)-3-甲基苯并咪唑啉鎓)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-***根)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑根)(4’,6’-二氟苯基吡啶根)銥(III)、雙(4’,6’-二氟苯基吡啶根)(3,5-雙(三氟甲基)-2-(2’-吡啶基)吡咯根)銥(III)、雙(4’,6’-二氟苯基吡啶根)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-***根)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-久洛尼定-9-烯基-4H-吡喃、4-(二氰基亞甲基)-2-甲基-6-(1,1,7,7-四甲基久洛尼定-9-烯基)-4H-吡喃、4-(二氰基亞甲基)-2-第三丁基-6-(1,1,7,7-四甲基久洛尼定-4-基-乙烯基)-4H-吡喃、參(二苯甲醯基甲烷)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’-二第三丁基-(2,2’)-聯吡啶]釕(III).雙(六氟磷酸根)、參(2-苯基喹啉)銥(III)、雙(2-苯基喹啉)(乙醯丙酮酸)銥(III)、2,8-二第三丁基-5,11-雙(4-第三丁基苯基)-
6,12-二苯基稠四苯、雙(2-苯基苯并噻唑根)(乙醯丙酮酸)銥(III)、5,10,15,20-四苯基四苯并卟啉鉑、雙(3-三氟甲基-5-(2-吡啶)-吡唑根)二甲基苯膦鋨(II)、雙(3-(三氟甲基)-5-(4-第三丁基吡啶基)-1,2,4-***根)二苯基甲基膦鋨(II)、雙(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-***)二甲基苯膦鋨(II)、雙(3-(三氟甲基)-5-(4-第三丁基吡啶基)-1,2,4-***根)二甲基苯膦鋨(II)、雙[2-(4-正己基苯基)喹啉](乙醯丙酮酸)銥(III)、參[2-(4-正己基苯基)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)吡啶根)銥(III)、雙(2-(9,9-二乙基-茀-2-基)-1-苯基-1H-苯并[d]咪唑根)(乙醯丙酮酸)銥(III)、雙(2-苯基吡啶)(3-(吡啶-2-基)-2H-香豆素-2-酮根)銥(III)、雙(2-苯基喹啉)(2,2,6,6-四甲基庚-3,5-二酮根)銥(III)、雙(苯基異喹啉)(2,2,6,6-四甲基庚-3,5-二酮根)銥(III)、雙(4-苯基噻吩并[3,2-c]吡啶根-N,C2’)乙醯丙酮酸銥(III)、(E)-2-(2-第三丁基-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)吡唑根)(甲基二苯膦)釕、雙[(4-正己基苯基)異喹啉](乙醯丙酮酸)銥(III)、八乙基卟吩鉑(II)、雙(2-甲基二苯并[f,h]喹惡啉)(乙醯丙酮酸)銥(IIl)、參[(4-正己基苯基)異喹啉]銥(III)等。
形成電子輸送層/電洞(hole)阻擋層的材料,可列舉8-羥基喹啉根-鋰、2,2’,2”-(1,3,5-苯甲苯基)-參(1-苯基-1-H-苯并咪唑)、2-(4-聯苯基)5-(4-第三丁基苯基)-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-喹啉根)-4-(苯基苯酚根)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-4-基)-1,3,4-噁二唑-2-基]-2,2’-聯吡啶、3-(4-聯苯基)-4-苯基-5-第三丁基苯基-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-第三丁基苯基)-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-二芘基氧化膦、3,3’,5,5’-四[(間吡啶基)-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]喹啉根)鈹、二苯基雙(4-(吡啶-3-基)苯基)矽烷、3,5-二(芘-1-基)吡啶等。
形成電子注入層的材料,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、Li(acac)、醋酸鋰、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。
形成電子阻擋層的材料可列舉參(苯基吡唑)銥等。
使用本發明之電荷輸送性清漆的PLED元件之製作方法並未受到特別限定,可列舉以下方法。
藉由以依序形成正電洞輸送性高分子層、發光性高分子層來代替在上述OLED元件製作過程中進行的正電洞輸送層、發光層、電子輸送層、電子注入層的真空蒸鍍操作,可製作出具有利用本發明之電荷輸送性清漆所形成的電荷輸送性薄膜的PLED元件。
具體而言,在陽極基板上塗佈本發明之電荷輸送性清漆,藉由上述方法製作出正電洞注入層,於其上依序形成正電洞輸送性高分子層、發光性高分子層,進一步蒸鍍陰極,而製成PLED元件。
所使用的陰極及陽極材料,可採用與上述OLED元件製作時同樣的材料,可進行同樣的洗淨處理、表面處理。
正電洞輸送性高分子層及發光性高分子層的形成方法,可列舉在正電洞輸送性高分子材料或發光性高分子材料、或在該等中加入摻雜物質所形成的材料中,加入溶劑使其溶解或均勻分散,塗佈在正電洞注入層或正電洞輸送性高分子層上,然後分別燒成而成膜的方法。
正電洞輸送性高分子材料,可列舉聚[(9,9-二己基茀基-2,7-二基)-co-(N,N’-雙{對丁基苯基}-1,4-二胺基伸苯基)]、聚[(9,9-二辛基茀基-2,7-二基)-co-(N,N’-雙{對丁基苯基}-1,1’-亞聯苯基-4,4-二胺)]、聚[(9,9-雙{1’-戊烯-5’-基}茀基-2,7-二基)-co-(N,N’-雙{對丁基苯基}-1,4-二胺基伸苯基)]、分子末端以聚倍半矽氧烷封端的聚[N,N’-雙(4-丁基苯基)-N,N’-雙(苯基)-聯苯胺]、聚[(9,9-二-二辛基茀基-2,7-二基)-co-(4,4’-(N-(對丁基苯基))二苯胺)]等。
發光性高分子材料可列舉聚(9,9-二烷基茀)(PDAF)等的聚茀衍生物、聚(2-甲氧基-5-(2’-乙基己氧基)-1,4-伸苯基伸乙烯基)(MEH-PPV)等的聚伸苯基伸乙烯基衍生物、聚(3-烷基噻吩)(PAT)等的聚噻吩衍生物、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、超音波分散等的方法。
塗佈方法並未受到特別限定,可列舉噴墨法、噴霧法、浸漬法、旋轉塗佈法、轉印印刷法、輥式塗佈法、刷毛塗佈等。此外,塗佈係以在氮氣、氬氣等的惰性氣體下進行為佳。
燒成的方法可列舉惰性氣體下或真空中,並在烘箱或熱板加熱的方法。
此外,不僅是由上述說明的電荷輸送性清漆
所得到的電荷輸送性薄膜,由本發明之苯胺衍生物所得到的蒸鍍膜的電荷輸送性亦優異,因此依照用途亦可採用藉由蒸鍍法所得到的電荷輸送性薄膜。
以下列舉製造例及實施例對本發明作較具體的說明,然而本發明並不受下述實施例所限定。此外,所使用的裝置如以下所述。
(1)1H-NMR:日本電子股份有限公司製 JNM-ECP300 FT NMR SYSTEM
(2)基板洗淨:長州產業股份有限公司製 基板洗淨裝置(減壓電漿式)
(3)清漆的塗佈:Mikasa股份有限公司製 旋轉塗佈機MS-A100
(4)膜厚測定:小坂研究所股份有限公司製 微細形狀測定機Surfcorder ET-4000
(5)EL元件的製作:長州產業股份有限公司製 多機能蒸鍍裝置系統C-E2L1G1-N
(6)EL元件的輝度等的測定:Tech-World有限公司製 I-V-L測定系統
(7)EL元件的壽命測定:EHC股份有限公司製 有機EL輝度壽命評估系統PEL-105S
[1]化合物的合成
[製造例1]N,N-(氧雙(4,1-伸苯基))雙(9-苯基-N-(9-苯基-9H-咔唑-3-基)-9H-咔唑-3-胺)(以下稱為苯胺衍生物1)的合成
將4,4’-氧二苯胺0.500g、3-溴-9-苯基-9H-咔唑3.54g、Pd(dba)258mg及第三丁氧基鈉1.39g裝入反應容器,對容器內實施氮氣置換,然後加入甲苯15mL及另外預先準備的三-第三丁基膦的甲苯溶液425μL(濃度:96g/L),並在50℃下攪拌4小時。冷卻至室溫,然後加入甲苯及飽和食鹽水進行分液。以無水硫酸鈉使有機層乾燥,然後濃縮。將濃縮液以二氧化矽膠體過濾,在所得到的濾液中加入活性碳0.1g,並在室溫下攪拌1小時。藉由過濾除去活性碳,並將濾液濃縮。將所得到的濃縮液滴入甲醇/醋酸乙酯(=250mL/250mL)中,在室溫下攪拌,將所產生的泥漿溶液過濾,使所得到的濾出物乾燥,而得到苯胺衍生物1(產量:2.47g)。
1H-NMR(300MHz,THF-d8)δ[ppm]:7.97-8.01(m,8H),7.59-7.65(m,16H),7.43-7.50(m,4H),7.24-7.37(m,16H),7.12(t,J=8.0Hz,4H),7.06
(d,J=8.9Hz,4H),6.90(d,J=8.9Hz,4H).
[製造例2]N,N’-(硫代雙(4,1-伸苯基))雙(9-苯基-N-(9-苯基-9H-咔唑-3-基)-9H-咔唑-3-胺)(以下稱為苯胺衍生物2)的合成
將4,4’-硫代二苯胺0.508g、3-溴-9-苯基-9H-咔唑3.32g、Pd(dba)253mg及第三丁氧基鈉1.31g裝入反應容器,對容器內實施氮氣置換,然後加入甲苯15mL及另外預先準備的三-第三丁基膦的甲苯溶液400μL(濃度:96g/L),並在50℃下攪拌3小時。冷卻至室溫,然後加入甲苯及飽和食鹽水進行分液。以無水硫酸鈉使有機層乾燥,然後濃縮。將濃縮液以二氧化矽膠體過濾,在所得到的濾液中加入活性碳0.1g,並在室溫下攪拌1小時。藉由過濾除去活性碳,並將濾液濃縮。將所得到的濃縮液滴至甲醇/醋酸乙酯(=250mL/250mL)中,在室溫下攪拌,將所產生的泥漿溶液過濾,並將所得到的濾出物以管柱層析(從甲苯/正己烷=90/10變化成甲苯/正己烷=100/0的梯度)精製。收集含有目標產物的部分並加以濃
縮,將所得到的濃縮液滴至甲醇(400mL)中,在室溫下攪拌1小時。將所得到的泥漿過濾,使其乾燥,而得到苯胺衍生物2(產量:2.48g)。
1H-NMR(300MHz,THF-d8)δ[ppm]:8.00-8.03(m,8H),7.61-7.69(m,16H),7.43-7.59(m,4H),7.26-7.37(m,16H),7.06-7.21(m,8H),6.96(d,J=8.9Hz,4H).
[製造例3]N1-(4-(雙(9-苯基-9H-咔唑-3-基)胺基)苯基)-N1-甲基N4,N4-雙(9-苯基-9H-咔唑-3-基)苯-1,4-二胺(以下稱為苯胺衍生物3)的合成
將N1-(4-胺基苯基)-N1-甲基苯-1,4-二胺0.502g、3-溴-9-苯基-9H-咔唑3.33g、Pd(dba)254mg、及第三丁氧基鈉1.37g裝入反應容器,對容器內實施氮氣置換,然後加入甲苯15mL及另外預先準備的三-第三丁基膦的甲苯溶液400μL(濃度:96g/L),在50℃下攪拌2小時。冷卻至室溫,然後加入甲苯及飽和食鹽水進行分液。以無水硫酸鈉使有機層乾燥,然後濃縮。將濃縮液以二氧
化矽膠體過濾,在所得到的濾液中加入活性碳0.1g,並在室溫下攪拌1小時。藉由過濾除去活性碳,並將濾液濃縮。所得到的濃縮液滴至甲醇/醋酸乙酯(=250mL/250mL)中,在室溫下攪拌,將所產生的泥漿溶液過濾,將所得到的濾出物以管柱層析(從甲苯/正己烷=90/10變化成甲苯/正己烷=100/0的梯度)精製。收集含有目標產物的部分並加以濃縮,將所得到的濃縮液滴至甲醇(400mL)中,並在室溫下攪拌1小時。將所得到的泥漿過濾,使其乾燥,而得到苯胺衍生物3(產量:2.46g)。
1H-NMR(300MHz,THF-d8)δ[ppm]:7.95-8.00(m,8H),7.59-7.65(m,16H),7.42-7.49(m,4H),7.23-7.37(m,16H),7.12(t,J=8.9Hz,4H),7.02(d,J=8.9Hz,4H),6.91(d,J=8.9Hz,4H),3.27(s,3H).
[2]電荷輸送性清漆之調製
[實施例1-1]
使作為電荷輸送性物質的苯胺衍生物1 0.046g、作為摻雜物質的磷鎢酸0.101g及四氟四氰基醌二甲烷(F4TCNQ)0.055g溶於1,3-二甲基-2-咪唑啶酮4.0g。於其中加入2,3-丁二醇4.5g以及乙基溶纖劑醋酸酯1.5g,並且攪拌,進一步於其中加入3,3,3-三氟丙基三甲氧基矽烷(信越化學工業股份有限公司製)0.003g及苯基三甲氧
基矽烷(信越化學工業股份有限公司製)0.007g,並且攪拌,而調製出電荷輸送性清漆。
[實施例1-2~1-3]
分別使用苯胺衍生物2 0.047g(實施例1-2)、苯胺衍生物3 0.047g(實施例1-3)來代替苯胺衍生物1 0.046g,除此之外以與實施例1-1同樣的方法調製出電荷輸送性清漆。
[3]有機EL元件之製造及特性評估
[實施例2-1]
使用旋轉塗佈機將實施例1-1所得到的清漆塗佈於ITO基板,然後在80℃下乾燥1分鐘,進一步在大氣環境下,並在150℃下燒成5分鐘,在ITO基板上形成30nm的均勻薄膜。ITO基板是採用氧化銦錫(ITO)在表面上以膜厚150nm圖型化而且大小為25mm×25mm×0.7t的玻璃基板,在使用前,藉由O2電漿洗淨裝置(150W、30秒鐘)除去表面上的雜質。
接下來,對於形成薄膜的ITO基板,使用蒸鍍裝置(真空度1.0×10-5Pa),使α-NPD以0.2nm/秒鐘成膜30nm。接下來,使CBP與Ir(PPy)共蒸鍍。共蒸鍍時,控制蒸鍍速率以使Ir(PPy)3的濃度成為6%,使其積層40nm。接下來,依序積層BAlq、氟化鋰及鋁的薄膜,而得到有機EL元件。此時,以BAlq及鋁的蒸鍍速率為
0.2nm/秒鐘、氟化鋰的蒸鍍速率為0.02nm/秒鐘的條件各自進行蒸鍍,膜厚分別為20nm、0.5nm及120nm。
此外,為了防止空氣中的氧氣、水等的影響造成特性劣化,有機EL元件是在藉由密封基板來密封之後評估其特性。密封是依照以下的順序進行。在氧氣濃度2ppm以下、露點-85℃以下的氮氣環境中,將有機EL元件收在密封基板之間,並以接著材(MORESCO股份有限公司製,MORESCO MOISTURE CUT WB90US(P))將密封基板貼合。此時,將吸水劑(Dynic股份有限公司製,HD-071010W-40)與有機EL元件一起收在密封基板內。對於貼合的密封基板照射UV光(波長:365nm、照射量:6,000mJ/cm2),然後在80℃下進行1小時退火處理,使接著材硬化。
[實施例2-2~2-3]
分別使用實施例1-2~1-3所得到的清漆來代替實施例1-1所得到的清漆,除此之外以與實施例2-1同樣的方法製作出有機EL元件。
對於所製作出的各元件測定驅動電流0.7mA時的驅動電壓、輝度及發光效率,以及輝度的半減期(將驅動電流保持在0.7mA,持續驅動元件時,輝度達到初期值的一半所須的時間)。將結果一併揭示於表1。此外,各元件的發光面尺寸的面積為2mm×2mm。
如表1所示般,可知具有由本發明之電荷輸送性清漆所得到的電荷輸送性薄膜作為正電洞注入層的有機EL元件,會表現出高輝度,耐久性亦優異。
Claims (16)
- 一種苯胺衍生物,其特徵為:由式(1)所表示,
- 如申請專利範圍第1項之苯胺衍生物,其中前述R1~R4全部為氫原子。
- 如申請專利範圍第1或2項之苯胺衍生物,其中前述Ar1互相獨立,而為由式(A1)~(A12)所表示之任一基。
- 如申請專利範圍第3項之苯胺衍生物,其中前述Ar1互相獨立,而為由式(A1)~(A3)、(A5)~(A7)、及(A10)~(A12)所表示之任一基。
- 如申請專利範圍第1~4項中任一項之苯胺衍生物,其中前述Ar1為相同之基。
- 一種電荷輸送性物質,其係由如申請專利範圍第1 ~5項中任一項之苯胺衍生物所構成。
- 一種電荷輸送性材料,其係含有如申請專利範圍第6項之電荷輸送性物質。
- 一種電荷輸送性清漆,其係含有如申請專利範圍第6項之電荷輸送性物質與有機溶劑。
- 如申請專利範圍第8項之電荷輸送性清漆,其中進一步含有摻雜物質。
- 如申請專利範圍第9項之電荷輸送性清漆,其中前述摻雜物質含有鹵代四氰基醌二甲烷化合物。
- 如申請專利範圍第10項之電荷輸送性清漆,其中前述摻雜物質進一步含有異聚酸。
- 一種電荷輸送性薄膜,其係使用如申請專利範圍第8~11項中任一項之電荷輸送性清漆所製作。
- 一種電子裝置,其係具有如申請專利範圍第12項之電荷輸送性薄膜。
- 一種有機電致發光元件,其係具有如申請專利範圍第12項之電荷輸送性薄膜。
- 一種電荷輸送性薄膜之製造方法,其特徵為:將如申請專利範圍第8~11項中任一項之電荷輸送性清漆塗佈在基材上,並使溶劑蒸發。
- 如申請專利範圍第1項之苯胺衍生物的製造方法,其係使由式(2)所表示之胺化合物在觸媒存在下與由式(3)所表示之芳香基化合物反應,
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EP0650955B1 (en) * | 1993-11-01 | 1998-08-19 | Hodogaya Chemical Co., Ltd. | Amine compound and electro-luminescence device comprising same |
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