JP2019127483A - 有機化合物、発光素子、発光装置、電子機器、および照明装置 - Google Patents
有機化合物、発光素子、発光装置、電子機器、および照明装置 Download PDFInfo
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- JP2019127483A JP2019127483A JP2019006322A JP2019006322A JP2019127483A JP 2019127483 A JP2019127483 A JP 2019127483A JP 2019006322 A JP2019006322 A JP 2019006322A JP 2019006322 A JP2019006322 A JP 2019006322A JP 2019127483 A JP2019127483 A JP 2019127483A
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- 125000003277 amino group Chemical group 0.000 claims abstract description 39
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- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
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- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
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- 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 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000007737 ion beam deposition Methods 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 1
- AOZVYCYMTUWJHJ-UHFFFAOYSA-K iridium(3+) pyridine-2-carboxylate Chemical compound [Ir+3].[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1 AOZVYCYMTUWJHJ-UHFFFAOYSA-K 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- 229910052748 manganese Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
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- WOYDRSOIBHFMGB-UHFFFAOYSA-N n,9-diphenyl-n-(9-phenylcarbazol-3-yl)carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 WOYDRSOIBHFMGB-UHFFFAOYSA-N 0.000 description 1
- XAWQWMLNBYNXJX-UHFFFAOYSA-N n,n-diphenyl-9-[4-(10-phenylanthracen-9-yl)phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC(=CC=3)C=3C4=CC=CC=C4C(C=4C=CC=CC=4)=C4C=CC=CC4=3)C2=CC=1)C1=CC=CC=C1 XAWQWMLNBYNXJX-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
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- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 229930184652 p-Terphenyl Natural products 0.000 description 1
- NRNFFDZCBYOZJY-UHFFFAOYSA-N p-quinodimethane Chemical class C=C1C=CC(=C)C=C1 NRNFFDZCBYOZJY-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 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
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- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
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- 239000004814 polyurethane Substances 0.000 description 1
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- 229960000286 proflavine Drugs 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 150000003216 pyrazines Chemical class 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
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
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- 125000005493 quinolyl group Chemical group 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 238000005507 spraying Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
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- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 125000005650 substituted phenylene group Chemical group 0.000 description 1
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- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JIIYLLUYRFRKMG-UHFFFAOYSA-N tetrathianaphthacene Chemical compound C1=CC=CC2=C3SSC(C4=CC=CC=C44)=C3C3=C4SSC3=C21 JIIYLLUYRFRKMG-UHFFFAOYSA-N 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 239000012780 transparent material Substances 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
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 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
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- CJGUQZGGEUNPFQ-UHFFFAOYSA-L zinc;2-(1,3-benzothiazol-2-yl)phenolate Chemical compound [Zn+2].[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1.[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1 CJGUQZGGEUNPFQ-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- H—ELECTRICITY
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- 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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- 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
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- H—ELECTRICITY
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- 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
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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Abstract
Description
本実施の形態では、本発明の一態様である有機化合物について説明する。
まず、上記一般式(G1)で表される、ジベンゾベンゾフロキノキサリン誘導体、またはジベンゾベンゾチエノキノキサリン誘導体の合成に用いる、ハロゲン化合物(一般式(G0))の合成方法について説明する。
上記一般式(G0)で表されるハロゲン化合物は、下記合成スキーム(A−1)に示すように、ヒドロキシ基またはスルファニル基が置換されたフェニル基を有する、ハロゲン化ジベンゾキノキサリン誘導体(A1)を炭酸カリウムなどの塩基(A2)と反応させることにより得ることができる。
上記一般式(G0)で表されるハロゲン化合物は、下記合成スキーム(A−1’)に示すように、メチルオキシ基またはメチルスルファニル基が置換されたフェニル基と、アミノ基を有するジベンゾキノキサリン誘導体(A1’)と、亜硝酸tert−ブチルとを反応させても得ることができる。
次に、上記一般式(G1)で表される、ジベンゾベンゾフロキノキサリン誘導体、またはジベンゾベンゾチエノキノキサリン誘導体の合成方法について説明する。
本実施の形態では、本発明の一態様である発光素子について説明する。なお、本実施の形態で説明する発光素子には、本発明の一態様である有機化合物を用いることができる。
図1(A)には、一対の電極間にEL層を挟んでなる発光素子を示す。具体的には、第1の電極101と第2の電極102との間に発光層を含むEL層103が挟まれた構造を有する。
次に、本発明の一態様である発光素子の具体的な構造および作製方法について説明する。なお、図1(A)〜図1(D)において、符号が共通である場合は説明も共通とする。
第1の電極101および第2の電極102を形成する材料としては、上述した素子構造における両電極の機能が満たせるのであれば、以下に示す材料を適宜組み合わせて用いることができる。例えば、金属、合金、電気伝導性化合物、およびこれらの混合物などを適宜用いることができる。具体的には、In−Sn酸化物(ITOともいう)、In−Si−Sn酸化物(ITSOともいう)、In−Zn酸化物、In−W−Zn酸化物が挙げられる。その他、アルミニウム(Al)、チタン(Ti)、クロム(Cr)、マンガン(Mn)、鉄(Fe)、コバルト(Co)、ニッケル(Ni)、銅(Cu)、ガリウム(Ga)、亜鉛(Zn)、インジウム(In)、スズ(Sn)、モリブデン(Mo)、タンタル(Ta)、タングステン(W)、パラジウム(Pd)、金(Au)、白金(Pt)、銀(Ag)、イットリウム(Y)、ネオジム(Nd)などの金属、およびこれらを適宜組み合わせて含む合金を用いることもできる。その他、上記例示のない元素周期表の第1族または第2族に属する元素(例えば、リチウム(Li)、セシウム(Cs)、カルシウム(Ca)、ストロンチウム(Sr))、ユウロピウム(Eu)、イッテルビウム(Yb)などの希土類金属およびこれらを適宜組み合わせて含む合金、その他グラフェン等を用いることができる。
正孔注入層(111、111a、111b)は、陽極である第1の電極101や電荷発生層(104)からEL層(103、103a、103b)に正孔(ホール)を注入する層であり、正孔注入性の高い材料を含む層である。
発光層(113、113a、113b、113c)は、発光物質を含む層である。なお、発光物質としては、青色、紫色、青紫色、緑色、黄緑色、黄色、橙色、赤色などの発光色を呈する物質を適宜用いる。また、複数の発光層(113a、113b、113c)に異なる発光物質を用いることにより異なる発光色を呈する構成(例えば、補色の関係にある発光色を組み合わせて得られる白色発光)とすることができる。さらに、一つの発光層が異なる発光物質を有する積層構造であっても良い。
電子輸送層(114、114a、114b)は、電子注入層(115、115a、115b)によって、第2の電極102から注入された電子を発光層(113、113a、113b、113c)に輸送する層である。なお、電子輸送層(114、114a、114b)は、電子輸送性材料を含む層である。電子輸送層(114、114a、114b)に用いる電子輸送性材料は、1×10−6cm2/Vs以上の電子移動度を有する物質が好ましい。なお、正孔よりも電子の輸送性の高い物質であれば、これら以外のものを用いることができる。本発明の一態様である有機化合物はこうした要求を満たす。加えてLUMO準位の低さは駆動電圧を下げることにつながるので、電子輸送層に本発明の一態様である有機化合物を用いる事は好ましい。その他の使いうる材料について以下に示す。
電子注入層(115、115a、115b)は、電子注入性の高い物質を含む層である。電子注入層(115、115a、115b)には、フッ化リチウム(LiF)、フッ化セシウム(CsF)、フッ化カルシウム(CaF2)、リチウム酸化物(LiOx)等のようなアルカリ金属、アルカリ土類金属、またはそれらの化合物を用いることができる。また、フッ化エルビウム(ErF3)のような希土類金属化合物を用いることができる。また、電子注入層(115、115a、115b)にエレクトライドを用いてもよい。エレクトライドとしては、例えば、カルシウムとアルミニウムの混合酸化物に電子を高濃度添加した物質等が挙げられる。なお、上述した電子輸送層(114、114a、114b)を構成する物質を用いることもできる。
図1(D)に示す発光素子において、電荷発生層104は、第1の電極(陽極)101と第2の電極(陰極)102との間に電圧を印加したときに、EL層103aに電子を注入し、EL層103bに正孔を注入する機能を有する。なお、電荷発生層104は、正孔輸送性材料に電子受容体(アクセプター)が添加された構成であっても、電子輸送性材料に電子供与体(ドナー)が添加された構成であってもよい。また、これらの両方の構成が積層されていても良い。なお、上述した材料を用いて電荷発生層104を形成することにより、EL層が積層された場合における駆動電圧の上昇を抑制することができる。
本実施の形態で示した発光素子は、様々な基板上に形成することができる。なお、基板の種類は、特定のものに限定されることはない。基板の一例としては、半導体基板(例えば単結晶基板又はシリコン基板)、SOI基板、ガラス基板、石英基板、プラスチック基板、金属基板、ステンレス・スチル基板、ステンレス・スチル・ホイルを有する基板、タングステン基板、タングステン・ホイルを有する基板、可撓性基板、貼り合わせフィルム、繊維状の材料を含む紙、又は基材フィルムなどが挙げられる。
本実施の形態では、本発明の一態様である発光装置について説明する。なお、図2(A)に示す発光装置は、第1の基板201上のトランジスタ(FET)202と発光素子(203R、203G、203B、203W)が電気的に接続されてなるアクティブマトリクス型の発光装置であり、複数の発光素子(203R、203G、203B、203W)は、共通のEL層204を有し、また、各発光素子の発光色に応じて、各発光素子の電極間の光学距離が調整されたマイクロキャビティ構造を有する。また、EL層204から得られた発光が第2の基板205に形成されたカラーフィルタ(206R、206G、206B)を介して射出されるトップエミッション型の発光装置である。
本実施の形態では、本発明の一態様である発光装置について説明する。
本実施の形態では、本発明の一態様である発光素子、本発明の一態様である発光素子を有する発光装置を適用して完成させた様々な電子機器や自動車の一例について、説明する。なお、発光装置は、本実施の形態で説明する電子機器において、主に表示部に適用することができる。
本実施の形態では、本発明の一態様である発光装置、またはその一部である発光素子を適用して作製される照明装置の構成について図7を用いて説明する。
本実施例では、実施の形態1の構造式(100)で表される本発明の一態様である有機化合物、13−[3−(ジベンゾチオフェン−4−イル)フェニル]ジベンゾ[f,h][1]ベンゾフロ[2,3−b]キノキサリン(略称:13mDBtPBfdbq)の合成方法について説明する。なお、13mDBtPBfdbqの構造を以下に示す。
フェナントレン−9,10−ジアミン塩酸塩5.97gと炭酸水素ナトリウム16.51g、シュウ酸ジエチル230mLを、還流管を付けた三口フラスコに入れ、内部を窒素置換した。その後、130℃で23時間撹拌することで反応させた。所定時間経過後、これに水1Lを加え、室温で30分撹拌した。その後、得られた混合物を吸引ろ過し、エタノールで洗浄することにより、目的のピラジン誘導体を得た(黄土色粉末、収量3.91g、収率61%)。ステップ1の合成スキームを下記式(a−1)に示す。
次に、上記ステップ1で得た、1,4−ジヒドロフェナントロ[9,10−b]ピラジン−2,3−ジオン3.91gと脱水DMF60mLを、還流管を付けた三口フラスコに入れ、内部を窒素置換した。フラスコを氷冷した後、塩化ホスホリル5.4mLを加え、100℃で7時間半攪拌した。所定時間経過後、得られた混合物を1M水酸化ナトリウム水溶液130mLに注いだ後、吸引ろ過した。得られた固体を水、エタノールで洗浄した後、トルエンに溶かし、セライトを通して濾過した。得られた濾液を濃縮することにより、目的のキノキサリン誘導体を得た(黄白色粉末、収量1.00g、収率22%)。ステップ2の合成スキームを下記式(a−2)に示す。
次に、上記ステップ2で得た、2,3−ジクロロジベンゾ[f,h]キノキサリン1.85g、5−クロロ−2−メトキシフェニルボロン酸1.16g、炭酸ナトリウム0.66g、エチレングリコールジメチルエーテル(略称:DME)27mL、水27mLを、還流管を付けた三口フラスコに入れ、内部を窒素置換した。フラスコ内を減圧下で撹拌して脱気した後、テトラキス(トリフェニルホスフィン)パラジウム(0)(略称:Pd(PPh3)4)0.48gを加え、100℃で20時間半撹拌し、反応させた。所定時間経過後、これに水を加え、吸引ろ過により得られた固体をジクロロメタンに溶解させて濾過し、濾液を濃縮させた。得られた固体を、トルエン:ヘキサン=1:2を展開溶媒とするシリカゲルカラムクロマトグラフィーにより精製し、目的のキノキサリン誘導体を得た(白色粉末、収量1.86g、収率74%)。ステップ3の合成スキームを下記式(a−3)に示す。
次に、上記ステップ3で得た、2−クロロ−3−(5−クロロ−2−メトキシフェニル)キノキサリン2.56g、脱水ジクロロメタン70mLを三口フラスコに入れ、内部を窒素置換した。フラスコを−20℃に冷却した後、三臭化ホウ素(1Mジクロロメタン溶液)13mLを滴下し、室温で16時間撹拌した。所定時間経過後、水を加え、ジクロロメタンによる抽出操作を行った。操作により得られた固体を、ジクロロメタンを展開溶媒とするシリカゲルカラムクロマトグラフィーにより精製し、目的のキノキサリン誘導体を得た(黄色粉末、収量2.12g、収率84%)。ステップ4の合成スキームを下記式(a−4)に示す。
次に、上記ステップ4で得た2−クロロ−3−(5−クロロ−2−ヒドロキシフェニル)キノキサリン2.12g、脱水N−メチル−2−ピロリドン(略称:NMP)27mLを、還流管を付けた三口フラスコに入れ、内部を窒素置換した。ここに炭酸カリウム1.51gを加えた後、120℃で8時間撹拌した。所定時間経過後、水を加え、得られた混合物を吸引ろ過した。得られた固体をエタノールで洗浄することにより、目的のキノキサリン誘導体を得た(淡黄色粉末、収量1.56g、収率84%)。ステップ5の合成スキームを下記式(a−5)に示す。
さらに、上記ステップ5で得た13−クロロジベンゾ[f,h][1]ベンゾフロ[2,3−b]キノキサリン0.78g、(ジベンゾチオフェン−4−イル)フェニル−3−ボロン酸1.10g、フッ化セシウム1.26g、メシチレン44mLを、還流管を付けた三口フラスコに入れ、内部を窒素置換した。フラスコ内を減圧下で撹拌することで脱気した後、トリス(ジベンジリデンアセトン)ジパラジウム(0)(略称:Pd2(dba)3)0.075g、2’−(ジシクロヘキシルホスフィノ)アセトフェノンエチレンケタール0.059gを加え、120℃で17時間半撹拌した。所定時間経過後、得られた混合物にエタノールを加えて吸引ろ過し、水、エタノールで洗浄した。得られた固体をトルエンで溶かし、セライト、アルミナ、セライトの順で積層した濾過補助剤を通して濾過して濃縮乾固した後、トルエンで再結晶することにより、目的物を得た(黄白色粉末、収量0.71g、収率56%)。得られた黄白色粉末0.70gを、トレインサブリメーション法により昇華精製した。昇華精製条件は、圧力2.7Pa、アルゴンガスを流量10.5mL/minで流しながら、330℃で固体を加熱した。昇華精製後、目的物の黄白色固体を収量0.56g、収率80%で得た。ステップ6の合成スキームを下記式(a−6)に示す。
本実施例で示す発光素子は、図10に示すように基板900上に形成された第1の電極901上に正孔注入層911、正孔輸送層912、発光層913、電子輸送層914、電子注入層915が順次積層され、電子注入層915上に第2の電極903が積層された構造を有する。
作製した各発光素子の動作特性について測定した。なお、測定は室温(25℃に保たれた雰囲気)で行った。また、結果を図11〜図14に示す。
本実施例では、実施の形態1の構造式(101)で表される本発明の一態様である有機化合物、13−[3−(ジベンゾフラン−4−イル)フェニル]ジベンゾ[f,h][1]ベンゾフロ[2,3−b]キノキサリン(略称:13mDBfPBfdbq)の合成方法について説明する。なお、13mDBfPBfdbqの構造を以下に示す。
本実施例で示す13mDBfPBfdbqは、実施例1で説明した13mDBtPBfdbqの合成方法と同様に、下記合成スキーム(b−1)に示す方法を用いて合成する。
本実施例では、実施の形態1の構造式(102)で表される本発明の一態様である有機化合物、13−[3−(9H−カルバゾール−9−イル)フェニル]ジベンゾ[f,h][1]ベンゾフロ[2,3−b]キノキサリン(略称:13mCzPBfdbq)の合成方法について説明する。なお、13mCzPBfdbqの構造を以下に示す。
本実施例で示す13mCzPBfdbqは、実施例1で説明した13mDBtPBfdbqの合成方法と同様に、下記合成スキーム(c−1)に示す方法を用いて合成する。
本実施例では、実施の形態1の構造式(110)で表される本発明の一態様である有機化合物、13−[3−(トリフェニレン−2−イル)フェニル]ジベンゾ[f,h][1]ベンゾフロ[2,3−b]キノキサリン(略称:13mTpPBfdbq)の合成方法について説明する。なお、13mTpPBfdbqの構造を以下に示す。
本実施例で示す13mTpPBfdbqは、実施例1で説明した13mDBtPBfdbqの合成方法と同様に、下記合成スキーム(d−1)に示す方法を用いて合成する。
本実施例では、実施の形態1の構造式(123)で表される本発明の一態様である有機化合物、13−[3−(9’−フェニル−3,3’−ビ−9H−カルバゾール−9−イル)フェニル]ジベンゾ[f,h][1]ベンゾフロ[2,3−b]キノキサリン(略称:13mPCCzPBfdbq)の合成方法について説明する。なお、13mPCCzPBfdbqの構造を以下に示す。
本実施例で示す13mPCCzPBfdbqは、実施例1で説明した13mDBtPBfdbqの合成方法と同様に、下記合成スキーム(e−1)に示す方法を用いて合成する。
本実施例では、実施の形態1の構造式(125)で表される本発明の一態様である有機化合物、13−(9’−フェニル−3,3’−ビ−9H−カルバゾール−9−イル)ジベンゾ[f,h][1]ベンゾフロ[2,3−b]キノキサリン(略称:13PCCzBfdbq)の合成方法について説明する。なお、13PCCzBfdbqの構造を以下に示す。
実施例1のステップ5で得た、13−クロロジベンゾ[f,h][1]ベンゾフロ[2,3−b]キノキサリン0.78g、9’−フェニル−3,3’−ビ−9H−カルバゾール0.90g、メシチレン22mLを、還流管を付けた三口フラスコに入れ、内部を窒素置換した。フラスコ内を減圧下で撹拌することで脱気した後、ナトリウムtert−ブトキシド0.42g、ビス(ジベンジリデンアセトン)パラジウム(0)(略称:Pd(dba)2)0.013g、2−ジシクロヘキシルホスフィノ−2’,6’−ジメトキシビフェニル(略称:S−Phos)0.018gを加え、150℃で13時間撹拌した。
102 第2の電極
103 EL層
103a、103b EL層
104 電荷発生層
111、111a、111b 正孔注入層
112、112a、112b 正孔輸送層
113、113a、113b 発光層
114、114a、114b 電子輸送層
115、115a、115b 電子注入層
200R、200G、200B 光学距離
201 第1の基板
202 トランジスタ(FET)
203R、203G、203B、203W 発光素子
204 EL層
205 第2の基板
206R、206G、206B カラーフィルタ
206R’、206G’、206B’ カラーフィルタ
207 第1の電極
208 第2の電極
209 黒色層(ブラックマトリックス)
210R、210G 導電層
301 第1の基板
302 画素部
303 駆動回路部(ソース線駆動回路)
304a、304b 駆動回路部(ゲート線駆動回路)
305 シール材
306 第2の基板
307 引き回し配線
308 FPC
309 FET
310 FET
311 FET
312 FET
313 第1の電極
314 絶縁物
315 EL層
316 第2の電極
317 発光素子
318 空間
900 基板
901 第1の電極
902 EL層
903 第2の電極
911 正孔注入層
912 正孔輸送層
913 発光層
914 電子輸送層
915 電子注入層
4000 照明装置
4001 基板
4002 発光素子
4003 基板
4004 第1の電極
4005 EL層
4006 第2の電極
4007 電極
4008 電極
4009 補助配線
4010 絶縁層
4011 封止基板
4012 シール材
4013 乾燥剤
4015 拡散板
4200 照明装置
4201 基板
4202 発光素子
4204 第1の電極
4205 EL層
4206 第2の電極
4207 電極
4208 電極
4209 補助配線
4210 絶縁層
4211 封止基板
4212 シール材
4213 バリア膜
4214 平坦化膜
4215 拡散板
5101 ライト
5102 ホイール
5103 ドア
5104 表示部
5105 ハンドル
5106 シフトレバー
5107 座席シート
5108 インナーリアビューミラー
7000 筐体
7001 表示部
7002 第2表示部
7003 スピーカ
7004 LEDランプ
7005 操作キー
7006 接続端子
7007 センサ
7008 マイクロフォン
7009 スイッチ
7010 赤外線ポート
7011 記録媒体読込部
7012 支持部
7013 イヤホン
7014 アンテナ
7015 シャッターボタン
7016 受像部
7018 スタンド
7020 カメラ
7021 外部接続部
7022、7023 操作用ボタン
7024 接続端子
7025 バンド、
7026 マイクロフォン
7027 時刻を表すアイコン
7028 その他のアイコン
7029 センサ
7030 スピーカ
7052、7053、7054 情報
9310 携帯情報端末
9311 表示部
9312 表示領域
9313 ヒンジ
9315 筐体
Claims (28)
- 一般式(G1)で表される有機化合物。
(式中、QはOまたはSを表し、R1〜R12の少なくとも一は、環を形成する炭素数が3〜30の置換もしくは無置換の、縮合芳香環または縮合複素芳香環のいずれかを有する第一の基であり、他はそれぞれ独立に、水素、ハロゲノ基、ヒドロキシ基、アミノ基、ニトロ基、または炭素数1〜50の基のいずれかを表す。) - 一般式(G1)で表される有機化合物。
(式中、QはOまたはSを表し、R1〜R12の少なくとも一は、環を形成する炭素数が3〜30の置換もしくは無置換の正孔輸送性の骨格を有する第一の基であり、他はそれぞれ独立に、水素、ハロゲノ基、ヒドロキシ基、アミノ基、ニトロ基、または炭素数1〜50の基のいずれかを表す。) - 一般式(G1)で表される有機化合物。
(式中、QはOまたはSを表し、R1〜R12の少なくとも一は、フルオレン骨格、フェナントレン骨格、トリフェニレン骨格、ナフタレン骨格、ジベンゾチオフェン骨格、ジベンゾフラン骨格、またはカルバゾール骨格のいずれかを有する第一の基であり、他はそれぞれ独立に、水素、ハロゲノ基、ヒドロキシ基、アミノ基、ニトロ基、または炭素数1〜50の基のいずれかを表す。) - 前記第一の基の総炭素数が、3〜100である請求項1乃至請求項3に記載の有機化合物。
- 一般式(G1)で表される有機化合物。
(式中、QはOまたはSを表し、R1〜R12の少なくとも一は、環を形成する炭素数が6〜24の置換もしくは無置換のアリーレン基、または環を形成する炭素数が3〜24の置換もしくは無置換のヘテロアリーレン基を介して下記一般式(A−1)〜(A−21)のいずれか一で示される構造が結合した第一の基であり、他はそれぞれ独立に、水素、ハロゲノ基、ヒドロキシ基、アミノ基、ニトロ基、または炭素数1〜50の基のいずれかを表す。)
(式中、Q’はOまたはSを表し、R13〜R24はそれぞれ独立に、水素、炭素数1〜6のアルキル基、環を形成する炭素数が5〜7の置換もしくは無置換のシクロアルキル基、置換もしくは無置換のフェニル基、または置換もしくは無置換のカルバゾリル基のいずれかを表す。) - 一般式(G1)で表される有機化合物。
(式中、QはOまたはSを表し、R1〜R12の少なくとも一は、下記一般式(A−1)〜(A−21)のいずれか一で示される第一の基であり、他はそれぞれ独立に、水素、ハロゲノ基、ヒドロキシ基、アミノ基、ニトロ基、または炭素数1〜50の基のいずれかを表す。)
(式中、Q’はOまたはSを表し、R13〜R24はそれぞれ独立に、水素、炭素数1〜6のアルキル基、環を形成する炭素数が5〜7の置換もしくは無置換のシクロアルキル基、置換もしくは無置換のフェニル基、または置換もしくは無置換のカルバゾリル基のいずれかを表す。) - 一般式(G1)で表される有機化合物。
(式中、QはOまたはSを表し、R3は、環を形成する炭素数が3〜30の置換もしくは無置換の、縮合芳香環または縮合複素芳香環のいずれかを有する第一の基であり、R1、R2およびR4〜R12はそれぞれ独立に、水素、ハロゲノ基、ヒドロキシ基、アミノ基、ニトロ基、または炭素数1〜50の基のいずれかを表す。) - 一般式(G1)で表される有機化合物。
(式中、QはOまたはSを表し、R3は、環を形成する炭素数が3〜30の置換もしくは無置換の正孔輸送性の骨格を有する第一の基であり、R1、R2およびR4〜R12はそれぞれ独立に、水素、ハロゲノ基、ヒドロキシ基、アミノ基、ニトロ基、または炭素数1〜50の基のいずれかを表す。) - 一般式(G1)で表される有機化合物。
(式中、QはOまたはSを表し、R3は、フルオレン骨格、フェナントレン骨格、トリフェニレン骨格、ナフタレン骨格、ジベンゾチオフェン骨格、ジベンゾフラン骨格、またはカルバゾール骨格のいずれかを有する第一の基であり、R1、R2およびR4〜R12はそれぞれ独立に、水素、ハロゲノ基、ヒドロキシ基、アミノ基、ニトロ基、または炭素数1〜50の基のいずれかを表す。) - R3の総炭素数が、3〜100である請求項7乃至請求項9に記載の有機化合物。
- 一般式(G1)で表される有機化合物。
(式中、QはOまたはSを表し、R3は、環を形成する炭素数が6〜24の置換もしくは無置換のアリーレン基、または環を形成する炭素数が3〜24の置換もしくは無置換のヘテロアリーレン基を介して下記一般式(A−1)〜(A−21)のいずれか一で示される構造が結合した第一の基であり、R1、R2およびR4〜R12はそれぞれ独立に、水素、ハロゲノ基、ヒドロキシ基、アミノ基、ニトロ基、または炭素数1〜50の基のいずれかを表す。)
(式中、Q’はOまたはSを表し、R13〜R24はそれぞれ独立に、水素、炭素数1〜6のアルキル基、環を形成する炭素数が5〜7の置換もしくは無置換のシクロアルキル基、置換もしくは無置換のフェニル基、または置換もしくは無置換のカルバゾリル基のいずれかを表す。) - 一般式(G1)で表される有機化合物。
(式中、QはOまたはSを表し、R3は、下記一般式(A−1)〜(A−21)のいずれか一で示される第一の基であり、R1、R2およびR4〜R12はそれぞれ独立に、水素、ハロゲノ基、ヒドロキシ基、アミノ基、ニトロ基、または炭素数1〜50の基のいずれかを表す。)
(式中、Q’はOまたはSを表し、R13〜R24はそれぞれ独立に、水素、炭素数1〜6のアルキル基、環を形成する炭素数が5〜7の置換もしくは無置換のシクロアルキル基、置換もしくは無置換のフェニル基、または置換もしくは無置換のカルバゾリル基のいずれかを表す。) - 前記炭素数1〜50の基は、アルキルオキシ基、アリールオキシ基、アルキル基で置換されたアミノ基、アリール基で置換されたアミノ基、シアノ基、カルボキシル基、アルキルオキシカルボニル基、アリールオキシカルボニル基、アルキル基で置換されたシリル基、アリール基で置換されたシリル基、アルキル基、シクロアルキル基、ヘテロアリール基、またはアリール基のいずれかである請求項1乃至請求項12に記載の有機化合物。
- 構造式(100)または構造式(125)で表される有機化合物。
- ジベンゾベンゾフロキノキサリン骨格またはジベンゾベンゾチエノキノキサリン骨格を有する有機化合物を用いた発光素子。
- ジベンゾベンゾフロキノキサリン骨格またはジベンゾベンゾチエノキノキサリン骨格を有する有機化合物と、三重項励起エネルギーを発光に変える物質と、を用いた発光素子。
- ジベンゾベンゾフロキノキサリン骨格またはジベンゾベンゾチエノキノキサリン骨格を有する有機化合物と、燐光材料と、を用いた発光素子。
- ジベンゾベンゾフロキノキサリン骨格またはジベンゾベンゾチエノキノキサリン骨格を有する有機化合物と、TADF材料と、を用いた発光素子。
- 前記有機化合物が、ジベンゾ[f,h][1]ベンゾフロ[2,3−b]キノキサリン骨格またはジベンゾ[f,h][1]ベンゾチエノ[2,3−b]キノキサリン骨格を有する、請求項15乃至請求項18に記載の発光素子。
- 請求項1乃至請求項14のいずれか一に記載の有機化合物を用いた発光素子。
- 一対の電極間にEL層を有し、
前記EL層は、請求項1乃至請求項14のいずれか一に記載の有機化合物を有する発光素子。 - 一対の電極間にEL層を有し、
前記EL層は、発光層を有し、
前記発光層は、請求項1乃至請求項14のいずれか一に記載の有機化合物を有する発光素子。 - 一対の電極間にEL層を有し、
前記EL層は、発光層を有し、
前記発光層は、請求項1乃至請求項14のいずれか一に記載の有機化合物と、発光物質として有機金属錯体と、を有する発光素子。 - 前記有機金属錯体が、イリジウム錯体である請求項23に記載の発光素子。
- 前記イリジウム錯体が、フェニルキノリン骨格を有する請求項24に記載の発光素子。
- 請求項15乃至請求項25のいずれか一に記載の発光素子と、
トランジスタ、または基板のいずれか一と、
を有する発光装置。 - 請求項26に記載の発光装置と、
マイク、カメラ、操作用ボタン、外部接続部、または、スピーカのいずれか一と、
を有する電子機器。 - 請求項26に記載の発光装置と、
筐体、カバー、または、支持台のいずれか一と、
を有する照明装置。
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US20190229278A1 (en) | 2019-07-25 |
US11462696B2 (en) | 2022-10-04 |
KR20190088911A (ko) | 2019-07-29 |
CN110054630B (zh) | 2024-04-26 |
JP2023113638A (ja) | 2023-08-16 |
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US20230027613A1 (en) | 2023-01-26 |
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