JP2010077124A - トリアゾール誘導体、トリアゾール誘導体を用いた発光素子、発光装置、電子機器及び照明機器 - Google Patents
トリアゾール誘導体、トリアゾール誘導体を用いた発光素子、発光装置、電子機器及び照明機器 Download PDFInfo
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- JP2010077124A JP2010077124A JP2009200054A JP2009200054A JP2010077124A JP 2010077124 A JP2010077124 A JP 2010077124A JP 2009200054 A JP2009200054 A JP 2009200054A JP 2009200054 A JP2009200054 A JP 2009200054A JP 2010077124 A JP2010077124 A JP 2010077124A
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- light
- layer
- emitting
- emitting element
- triazole derivative
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- 150000003852 triazoles Chemical class 0.000 title claims abstract description 99
- 239000000463 material Substances 0.000 claims abstract description 57
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims description 71
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 abstract description 7
- 239000010410 layer Substances 0.000 description 222
- 150000001875 compounds Chemical class 0.000 description 44
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 230000032258 transport Effects 0.000 description 34
- 239000000758 substrate Substances 0.000 description 31
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- -1 4- (pyridyl) phenyl group Chemical group 0.000 description 20
- 230000005525 hole transport Effects 0.000 description 19
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- 230000005284 excitation Effects 0.000 description 15
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- FQJLLPQGVZXONM-UHFFFAOYSA-N 3-[4-(3,5-diphenyl-1,2,4-triazol-4-yl)phenyl]pyridine Chemical compound C1=CC=CC=C1C(N1C=2C=CC(=CC=2)C=2C=NC=CC=2)=NN=C1C1=CC=CC=C1 FQJLLPQGVZXONM-UHFFFAOYSA-N 0.000 description 6
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- 238000005481 NMR spectroscopy Methods 0.000 description 6
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- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 5
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
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- GRRIYLZJLGTQJX-UHFFFAOYSA-N 1,2-dibenzoylhydrazine Chemical compound C=1C=CC=CC=1C(=O)NNC(=O)C1=CC=CC=C1 GRRIYLZJLGTQJX-UHFFFAOYSA-N 0.000 description 4
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 4
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
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- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
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- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 4
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- UYROTQZLUVRLJT-UHFFFAOYSA-N 4-(4-bromophenyl)-3,5-diphenyl-1,2,4-triazole Chemical compound C1=CC(Br)=CC=C1N1C(C=2C=CC=CC=2)=NN=C1C1=CC=CC=C1 UYROTQZLUVRLJT-UHFFFAOYSA-N 0.000 description 3
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- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- UDYREAXKUIATRL-UHFFFAOYSA-N n,n-diphenyl-4-[1-[4-(n-phenylanilino)phenyl]cyclohexyl]aniline Chemical compound C1CCCCC1(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 UDYREAXKUIATRL-UHFFFAOYSA-N 0.000 description 1
- LKRBRJVNQJYRHZ-UHFFFAOYSA-N n,n-diphenyl-4-[9-[4-(n-phenylanilino)phenyl]fluoren-9-yl]aniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C1(C2=CC=CC=C2C2=CC=CC=C21)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 LKRBRJVNQJYRHZ-UHFFFAOYSA-N 0.000 description 1
- CRWAGLGPZJUQQK-UHFFFAOYSA-N n-(4-carbazol-9-ylphenyl)-4-[2-[4-(n-(4-carbazol-9-ylphenyl)anilino)phenyl]ethenyl]-n-phenylaniline Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=CC=1C=CC(C=C1)=CC=C1N(C=1C=CC(=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 CRWAGLGPZJUQQK-UHFFFAOYSA-N 0.000 description 1
- RFBDMIDJTYEWSG-UHFFFAOYSA-N n-(4-carbazol-9-ylphenyl)-9,9-dimethyl-n-phenylfluoren-2-amine Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1N(C=1C=CC(=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 RFBDMIDJTYEWSG-UHFFFAOYSA-N 0.000 description 1
- AJNJGJDDJIBTBP-UHFFFAOYSA-N n-(9,10-diphenylanthracen-2-yl)-n,9-diphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C(C=3C=CC=CC=3)=C3C=CC=CC3=C(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 AJNJGJDDJIBTBP-UHFFFAOYSA-N 0.000 description 1
- LBFXFIPIIMAZPK-UHFFFAOYSA-N n-[4-[4-(n-phenanthren-9-ylanilino)phenyl]phenyl]-n-phenylphenanthren-9-amine Chemical group 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
- KUGSVDXBPQUXKX-UHFFFAOYSA-N n-[9,10-bis(2-phenylphenyl)anthracen-2-yl]-n,9-diphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C(C=3C(=CC=CC=3)C=3C=CC=CC=3)=C3C=CC=CC3=C(C=3C(=CC=CC=3)C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 KUGSVDXBPQUXKX-UHFFFAOYSA-N 0.000 description 1
- SAZIGIAVMOYTBU-UHFFFAOYSA-N n-[chloro(phenyl)methylidene]benzenecarbohydrazonoyl chloride Chemical compound C=1C=CC=CC=1C(Cl)=NN=C(Cl)C1=CC=CC=C1 SAZIGIAVMOYTBU-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 238000001420 photoelectron spectroscopy Methods 0.000 description 1
- 230000001443 photoexcitation Effects 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- VLRICFVOGGIMKK-UHFFFAOYSA-N pyrazol-1-yloxyboronic acid Chemical compound OB(O)ON1C=CC=N1 VLRICFVOGGIMKK-UHFFFAOYSA-N 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
- 150000002909 rare earth metal compounds Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- QGJSAGBHFTXOTM-UHFFFAOYSA-K trifluoroerbium Chemical compound F[Er](F)F QGJSAGBHFTXOTM-UHFFFAOYSA-K 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- OYQCBJZGELKKPM-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O-2].[Zn+2].[O-2].[In+3] OYQCBJZGELKKPM-UHFFFAOYSA-N 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
- GWDUZCIBPDVBJM-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzothiazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1 GWDUZCIBPDVBJM-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
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- H10K50/14—Carrier transporting layers
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
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- Physics & Mathematics (AREA)
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- Plural Heterocyclic Compounds (AREA)
Abstract
【解決手段】一般式(G1)で表される構造を有するトリアゾール誘導体
(式中、Pyはピリジル基を表す。また、R11〜R12は水素、または炭素数1〜4のアルキル基、または炭素数1〜4のアルコキシ基もしくは、フェニル基を表す。)
【選択図】なし
Description
(式中、Pyは2−ピリジル基、または3−ピリジル基、または4−ピリジル基を表す。また、R11〜R12は水素、または炭素数1〜4のアルキル基、または炭素数1〜4のアルコキシ基もしくは、フェニル基を表す。)
(式中、Pyは2−ピリジル基、または3−ピリジル基、または4−ピリジル基を表す。)
また、上述の一般式(G2)で表されるトリアゾール誘導体において、3−ピリジル基、すなわちピリジル基がメタ位でフェニル基と結合している場合、特に電子輸送性が優れるため好ましい。この場合、本発明の一態様のトリアゾール誘導体は、下記の構造式(1)で表される。したがって、本発明の好ましい様態は、下記の構造式(1)で表されるトリアゾール誘導体である。
本実施の形態では、本発明の一態様のトリアゾール誘導体について説明する。本発明の一態様のトリアゾール誘導体は、電子輸送性かつ三重項エネルギーが大きいトリアゾール骨格に、電子輸送性に優れた性質を有するピリジル基を持っている。
(式中、Pyは2−ピリジル基、または3−ピリジル基、または4−ピリジル基を表す。また、R11、R12は水素、または炭素数1〜4のアルキル基、または炭素数1〜4のアルコキシ基もしくは、フェニル基を表す。)
(式中、Pyは2−ピリジル基、または3−ピリジル基、または4−ピリジル基を表す。)
一般式(G1)で表されるトリアゾール誘導体は、アリールカルボン酸のエステルから合成したハロゲン化トリアゾール誘導体と、ピリジンのボロン酸又はピリジンの化合物を有機ホウ素で置換した化合物とを、鈴木・宮浦反応によりカップリングして合成できる。
(式中、R1はアルキル基を表す。R11およびR12は水素、または炭素数1〜4のアルキル基、または炭素数1〜4のアルコキシル基またはフェニル基のいずれかを表す。また、X1およびX2はハロゲン基を表す。)
(式中、R2およびR3は水素またはアルキル基を表す。また、R2とR3は互いに結合して環を形成していても良い。X2はハロゲン基又はトリフラート基を表す。R11およびR12は、水素、または炭素数1〜4のアルキル基、または炭素数1〜4のアルコキシル基またはフェニル基のいずれかを表す。また、Pyはピリジル基を表す。)
本実施の形態2では、本発明の一態様のトリアゾール誘導体を燐光性化合物のホスト材料として用いた発光素子の態様について、図1を用いて説明する。
本実施の形態3では、実施形態2で示した構成と異なる構成の発光素子について説明する。
本発明の一態様の発光素子は、複数の発光層を有するものであってよい。複数の発光層を設け、それぞれの発光層から発光させることで、複数の発光が混合された発光を得ることができる。したがって、例えば白色光を得ることができる。本実施の形態4では、複数の発光層を有する発光素子の態様について図2を用いて説明する。
本実施の形態5では、本発明の一態様のトリアゾール誘導体を用いて作製された発光装置について図3乃至4を用いて説明する。なお、図3(A)は、発光装置を示す上面図、図3(B)は図3(A)をA−A’で切断した断面図である。点線で示された401は駆動回路部(ソース側駆動回路)、402は画素部、403は駆動回路部(ゲート側駆動回路)である。また、404は封止基板、405はシール材であり、シール材405で囲まれた内側は、空間407になっている。
本実施の形態では、実施の形態5に示す発光装置をその一部に含む本発明の一態様の電子機器について説明する。本発明の一態様の電子機器は、実施の形態1に示したトリアゾール誘導体を含み、発光効率の高く、消費電力が低減され、長時間駆動可能な表示部を有する。また、色再現性に優れた表示部を有する。
本実施例では実施の形態1に構造式(1)として示したトリアリールアミン誘導体である3−(4−(3,5−ジフェニル−4H−1,2,4−トリアゾール−4−イル)フェニル)ピリジン(略称:Py−TAZ)の合成方法について説明する。
ベンゾヒドラジドの合成スキームを(b−1)に示す。
1,2−ジベンゾイルヒドラジンの合成スキームを(b−2)に示す。
1,2−ビス[クロロ(フェニル)メチリデン]ヒドラゾンの合成スキームを(b−3)に示す。
4−(4−ブロモフェニル)−3,5−ジフェニル−4H−1,2,4−トリアゾールの合成スキームを(b−4)に示す。
3−(4−(3,5−ジフェニル−4H−1,2,4−トリアゾール−4−イル)フェニル)ピリジン(略称:Py−TAZ)の合成スキームを(b−5)に示す。
まず、ガラス基板2100上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、第1の電極2101を形成した。なお、その膜厚は110nmとし、電極面積は2mm×2mmとした。
発光素子1を形成した基板と同一基板上に、電子輸送層2114としてTAZ01の代わりに構造式(1)で表される3−(4−(3,5−ジフェニル−4H−1,2,4−トリアゾール−4−イル)フェニル)ピリジン(略称:Py−TAZ)を用いて、発光素子1と同様に発光素子2を作製した。
101 電極
102 電極
111 正孔注入層
112 正孔輸送層
113 発光層
114 電子輸送層
115 電子注入層
301 電極
302 電極
311 正孔注入層
312 正孔輸送層
313 発光層
314 電子輸送層
315 正孔輸送層
316 発光層
317 電子輸送層
318 電子注入層
321 N層
322 P層
401 ソース側駆動回路
402 画素部
403 ゲート側駆動回路
404 封止基板
405 シール材
407 空間
408 配線
409 FPC(フレキシブルプリントサーキット)
410 基板
411 スイッチング用TFT
412 電流制御用TFT
413 電極
414 絶縁物
416 層
417 電極
418 発光素子
423 nチャネル型TFT
424 pチャネル型TFT
951 基板
952 電極
953 絶縁層
954 隔壁層
955 発光物質を含む層
956 電極
1002 表示部
2001 筐体
2002 光源
2100 ガラス基板
2101 電極
2102 電極
2111 層
2112 正孔輸送層
2113 発光層
2114 電子輸送層
2115 電子注入層
3001 照明装置
3002 テレビ装置
9101 筐体
9102 支持台
9103 表示部
9104 スピーカー部
9105 ビデオ入力端子
9201 本体
9202 筐体
9203 表示部
9204 キーボード
9205 外部接続ポート
9206 ポインティングデバイス
9501 本体
9502 表示部
9503 筐体
9504 外部接続ポート
9505 リモコン受信部
9506 受像部
9507 バッテリー
9508 音声入力部
9509 操作キー
9510 接眼部
9601 筐体
9602 液晶層
9603 バックライト
9604 筐体
9605 ドライバーIC
9606 端子
Claims (9)
- 一般式(G1)で表される構造を有するトリアゾール誘導体。
(式中、Pyは2−ピリジル基、または3−ピリジル基、または4−ピリジル基を表す。また、R11〜R12は水素、または炭素数1〜4のアルキル基、または炭素数1〜4のアルコキシ基もしくは、フェニル基を表す。) - 一般式(G2)で表される構造を有するトリアゾール誘導体。
(式中、Pyは2−ピリジル基、または3−ピリジル基、または4−ピリジル基を表す。) - 構造式(1)で表されるトリアゾール誘導体。
- 一対の電極間に請求項1乃至請求項3のいずれか一項に記載のトリアゾール誘導体を含む発光素子。
- 請求項1乃至請求項3のいずれか一項に記載のトリアゾール誘導体と燐光を発する物質を含む発光層を一対の電極間に有する発光素子。
- 発光物質を含む発光層を陰極と陽極の間に有する発光素子において、
前記発光層と前記陰極の間に、請求項1乃至請求項3のいずれか一項に記載のトリアゾール誘導体からなる層を前記発光層に接して設けたことを特徴とする発光素子。 - 請求項1乃至請求項3のいずれか一項に記載のトリアゾール誘導体と燐光を発する物質を含む発光層を陰極と陽極の間に有する発光素子において、
前記発光層と前記陰極の間に、請求項1乃至請求項3のいずれか一項に記載のトリアゾール誘導体からなる層を前記発光層に接して設けたことを特徴とする発光素子。 - 請求項4乃至7に記載の発光素子と、前記発光素子の発光を制御する制御手段とを有する発光装置。
- 請求項4乃至7に記載の発光素子と、前記発光素子の発光を制御する制御手段とを備えた表示部を有することを特徴とする電子機器。
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