JP4780696B2 - 燐光発光性高分子化合物およびこれを用いた有機発光素子 - Google Patents
燐光発光性高分子化合物およびこれを用いた有機発光素子 Download PDFInfo
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- JP4780696B2 JP4780696B2 JP2004247948A JP2004247948A JP4780696B2 JP 4780696 B2 JP4780696 B2 JP 4780696B2 JP 2004247948 A JP2004247948 A JP 2004247948A JP 2004247948 A JP2004247948 A JP 2004247948A JP 4780696 B2 JP4780696 B2 JP 4780696B2
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- 229920000642 polymer Polymers 0.000 title claims description 61
- 150000001875 compounds Chemical class 0.000 title claims description 59
- 125000004432 carbon atom Chemical group C* 0.000 claims description 69
- 239000000178 monomer Substances 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 25
- 125000000962 organic group Chemical group 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 125000004434 sulfur atom Chemical group 0.000 claims description 23
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 21
- 238000011282 treatment Methods 0.000 claims description 18
- 125000004429 atom Chemical group 0.000 claims description 13
- 238000009832 plasma treatment Methods 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 239000007789 gas Substances 0.000 claims description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 5
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052786 argon Inorganic materials 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 65
- 239000010410 layer Substances 0.000 description 51
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 238000000034 method Methods 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 32
- 229920001577 copolymer Polymers 0.000 description 31
- 239000000463 material Substances 0.000 description 29
- 238000005160 1H NMR spectroscopy Methods 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- 239000003446 ligand Substances 0.000 description 25
- 239000012300 argon atmosphere Substances 0.000 description 16
- 230000005525 hole transport Effects 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 125000005647 linker group Chemical group 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- 238000005259 measurement Methods 0.000 description 13
- 238000010898 silica gel chromatography Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000012046 mixed solvent Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 229910052741 iridium Inorganic materials 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 229920001940 conductive polymer Polymers 0.000 description 10
- 239000010408 film Substances 0.000 description 10
- 238000005227 gel permeation chromatography Methods 0.000 description 10
- 239000002861 polymer material Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 150000003613 toluenes Chemical class 0.000 description 10
- 229910052723 transition metal Inorganic materials 0.000 description 10
- 150000003624 transition metals Chemical class 0.000 description 10
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 9
- -1 etc.) Substances 0.000 description 9
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000001555 benzenes Chemical class 0.000 description 8
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 238000007740 vapor deposition Methods 0.000 description 8
- 239000004793 Polystyrene Substances 0.000 description 7
- 239000007877 V-601 Substances 0.000 description 7
- 238000007334 copolymerization reaction Methods 0.000 description 7
- 238000009826 distribution Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229920002223 polystyrene Polymers 0.000 description 7
- 238000001556 precipitation Methods 0.000 description 7
- XYKIUTSFQGXHOW-UHFFFAOYSA-N propan-2-one;toluene Chemical compound CC(C)=O.CC1=CC=CC=C1 XYKIUTSFQGXHOW-UHFFFAOYSA-N 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 238000001226 reprecipitation Methods 0.000 description 7
- 125000006617 triphenylamine group Chemical group 0.000 description 7
- 238000001291 vacuum drying Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical group C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 5
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000004926 polymethyl methacrylate Substances 0.000 description 5
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 5
- QKYZQKJXAKNEPA-UHFFFAOYSA-N 3-hydroxy-5-methyl-1-phenylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound O=C1N(O)C(=O)C=2C(C)=CSC=2N1C1=CC=CC=C1 QKYZQKJXAKNEPA-UHFFFAOYSA-N 0.000 description 4
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229910052792 caesium Inorganic materials 0.000 description 4
- 238000007872 degassing Methods 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- 238000005530 etching Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 230000022244 formylation Effects 0.000 description 4
- 238000006170 formylation reaction Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 150000002460 imidazoles Chemical class 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 4
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 4
- 150000004866 oxadiazoles Chemical class 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- 150000004322 quinolinols Chemical class 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 150000003918 triazines Chemical class 0.000 description 4
- 238000006886 vinylation reaction Methods 0.000 description 4
- VWQMLEUOYVLSNW-UHFFFAOYSA-N 2-methyl-4-[3-methyl-4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]-n-(3-methylphenyl)aniline Chemical compound CC1=CC=CC(NC=2C(=CC(=CC=2)C=2C=C(C)C(N(C=3C=C(C)C=CC=3)C=3C=C(C)C=CC=3)=CC=2)C)=C1 VWQMLEUOYVLSNW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 101000606537 Homo sapiens Receptor-type tyrosine-protein phosphatase delta Proteins 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- 102100039666 Receptor-type tyrosine-protein phosphatase delta Human genes 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 2
- FDRNXKXKFNHNCA-UHFFFAOYSA-N 4-(4-anilinophenyl)-n-phenylaniline Chemical compound C=1C=C(C=2C=CC(NC=3C=CC=CC=3)=CC=2)C=CC=1NC1=CC=CC=C1 FDRNXKXKFNHNCA-UHFFFAOYSA-N 0.000 description 2
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 229910000573 alkali metal alloy Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- ANUZKYYBDVLEEI-UHFFFAOYSA-N butane;hexane;lithium Chemical compound [Li]CCCC.CCCCCC ANUZKYYBDVLEEI-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
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- 229910052700 potassium Inorganic materials 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 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 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- SYSZENVIJHPFNL-UHFFFAOYSA-N (alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform B (protein) Chemical compound COC1=CC=C(I)C=C1 SYSZENVIJHPFNL-UHFFFAOYSA-N 0.000 description 1
- WGGLDBIZIQMEGH-UHFFFAOYSA-N 1-bromo-4-ethenylbenzene Chemical compound BrC1=CC=C(C=C)C=C1 WGGLDBIZIQMEGH-UHFFFAOYSA-N 0.000 description 1
- VLCPISYURGTGLP-UHFFFAOYSA-N 1-iodo-3-methylbenzene Chemical compound CC1=CC=CC(I)=C1 VLCPISYURGTGLP-UHFFFAOYSA-N 0.000 description 1
- UDHAWRUAECEBHC-UHFFFAOYSA-N 1-iodo-4-methylbenzene Chemical compound CC1=CC=C(I)C=C1 UDHAWRUAECEBHC-UHFFFAOYSA-N 0.000 description 1
- YRAJNWYBUCUFBD-UHFFFAOYSA-N 2,2,6,6-tetramethylheptane-3,5-dione Chemical compound CC(C)(C)C(=O)CC(=O)C(C)(C)C YRAJNWYBUCUFBD-UHFFFAOYSA-N 0.000 description 1
- NRSBAUDUBWMTGL-UHFFFAOYSA-N 2-(1-benzothiophen-2-yl)pyridine Chemical compound S1C2=CC=CC=C2C=C1C1=CC=CC=N1 NRSBAUDUBWMTGL-UHFFFAOYSA-N 0.000 description 1
- DQBAIUFSLSHYOX-UHFFFAOYSA-N 2-methyl-4-[3-methyl-4-(3-methylanilino)phenyl]-n-(3-methylphenyl)aniline Chemical compound CC1=CC=CC(NC=2C(=CC(=CC=2)C=2C=C(C)C(NC=3C=C(C)C=CC=3)=CC=2)C)=C1 DQBAIUFSLSHYOX-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910017073 AlLi Inorganic materials 0.000 description 1
- 241001136782 Alca Species 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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Images
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| US20080050604A1 (en) * | 2004-05-21 | 2008-02-28 | Yoshiaki Takahashi | Polymer Light-Emitting Material and Organic Light Emitting Element |
| WO2007020881A1 (en) | 2005-08-17 | 2007-02-22 | Showa Denko K.K. | Organic electroluminescence device using a copolymer and a phosphorescent compound |
| JP2007157738A (ja) * | 2005-11-30 | 2007-06-21 | Showa Denko Kk | 避難誘導灯 |
| DE602006012229D1 (de) | 2005-12-22 | 2010-03-25 | Showa Denko Kk | Organische lichtemittierende vorrichtung |
| JP2007173057A (ja) * | 2005-12-22 | 2007-07-05 | Showa Denko Kk | 有機エレクトロルミネッセンス素子の製造方法、有機エレクトロルミネッセンス素子およびその用途 |
| JP2007236705A (ja) * | 2006-03-09 | 2007-09-20 | Showa Denko Kk | 陳列棚用の柵および陳列棚 |
| GB0617167D0 (en) | 2006-08-31 | 2006-10-11 | Cdt Oxford Ltd | Compounds for use in opto-electrical devices |
| JP5342103B2 (ja) * | 2006-10-16 | 2013-11-13 | 昭和電工株式会社 | 有機発光素子 |
| WO2008053935A1 (en) | 2006-11-01 | 2008-05-08 | Showa Denko K.K. | Cyclic siloxane compound, organic electroluminescent element, and use thereof |
| JP2008280524A (ja) * | 2007-04-13 | 2008-11-20 | Hitachi Chem Co Ltd | 有機エレクトロニクス用材料、有機エレクトロニクス素子および有機エレクトロルミネセンス素子 |
| JPWO2009063757A1 (ja) * | 2007-11-14 | 2011-03-31 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法、表示装置及び照明装置 |
| JP2011509241A (ja) * | 2007-12-21 | 2011-03-24 | ジョージア・テック・リサーチ・コーポレーション | ビス−オキサジアゾール部分をベースとするＲｏｍｐ−重合可能な電子輸送材料 |
| US20110001423A1 (en) | 2008-02-15 | 2011-01-06 | Showa Denko K.K. | Process for treating an electrode surface, electrode, and process for manufacturing organic electroluminescence devices |
| US20120068167A1 (en) | 2009-05-19 | 2012-03-22 | Showa Denko K.K. | Surface treatment method for electrodes, electrode, and process for producing organic electroluminescent element |
| US8735875B2 (en) | 2009-07-21 | 2014-05-27 | Showa Denko K.K. | Light emitting element, method for manufacturing light emitting element, image display device, and illuminating device |
| JP5856483B2 (ja) | 2009-10-27 | 2016-02-09 | 三星電子株式会社Ｓａｍｓｕｎｇ Ｅｌｅｃｔｒｏｎｉｃｓ Ｃｏ．，Ｌｔｄ． | 陽極バッファ層用組成物、陽極バッファ層用高分子化合物、有機エレクトロルミネッセンス素子、その製造方法およびその用途 |
| JPWO2012029156A1 (ja) | 2010-09-02 | 2013-10-28 | 昭和電工株式会社 | Ｅｌ素子、ｅｌ素子の製造方法、表示装置および照明装置 |
| US10319912B2 (en) | 2015-01-29 | 2019-06-11 | Samsung Electronics Co., Ltd. | Charge-transporting material and organic light-emitting device including the same |
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| JPH101665A (ja) * | 1996-06-18 | 1998-01-06 | Toyota Central Res & Dev Lab Inc | 電界発光素子 |
| JP2002037817A (ja) * | 2000-07-28 | 2002-02-06 | Jsr Corp | 正孔輸送材料 |
| JP2002124390A (ja) * | 2000-10-16 | 2002-04-26 | Jsr Corp | 有機エレクトロルミネッセンス素子 |
| JP4035976B2 (ja) * | 2001-10-02 | 2008-01-23 | 昭和電工株式会社 | 重合性化合物およびその製造方法 |
| JP3893949B2 (ja) * | 2001-11-15 | 2007-03-14 | 昭和電工株式会社 | 重合性化合物およびその製造方法 |
| JP2003137936A (ja) * | 2001-08-20 | 2003-05-14 | Kawamura Inst Of Chem Res | 重合体、その製造方法及び有機エレクトロルミネッセンス素子 |
| JP2003192730A (ja) * | 2001-12-26 | 2003-07-09 | Kawamura Inst Of Chem Res | マレイン酸無水物重合体、その製造方法及び有機エレクトロルミネッセンス素子 |
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