JP6309317B2 - 発光素子及び化合物 - Google Patents
発光素子及び化合物 Download PDFInfo
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- JP6309317B2 JP6309317B2 JP2014059820A JP2014059820A JP6309317B2 JP 6309317 B2 JP6309317 B2 JP 6309317B2 JP 2014059820 A JP2014059820 A JP 2014059820A JP 2014059820 A JP2014059820 A JP 2014059820A JP 6309317 B2 JP6309317 B2 JP 6309317B2
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- 150000001875 compounds Chemical class 0.000 title claims description 49
- -1 anthracene compound Chemical class 0.000 claims description 134
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 28
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- 125000004076 pyridyl group Chemical group 0.000 claims description 11
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- AZFHXIBNMPIGOD-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one iridium Chemical compound [Ir].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O AZFHXIBNMPIGOD-UHFFFAOYSA-N 0.000 description 7
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- 229910052697 platinum Inorganic materials 0.000 description 7
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
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- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 6
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- GJLCPQHEVZERAU-UHFFFAOYSA-N 2-(3-dibenzothiophen-4-ylphenyl)-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=CC(C=2C=3SC4=CC=CC=C4C=3C=CC=2)=C1 GJLCPQHEVZERAU-UHFFFAOYSA-N 0.000 description 5
- 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 5
- VDHOGVHFPFGPIP-UHFFFAOYSA-N 9-[3-[5-(3-carbazol-9-ylphenyl)pyridin-3-yl]phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(C=2C=NC=C(C=2)C=2C=CC=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 VDHOGVHFPFGPIP-UHFFFAOYSA-N 0.000 description 5
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- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
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- COVCYOMDZRYBNM-UHFFFAOYSA-N n-naphthalen-1-yl-9-phenyl-n-(9-phenylcarbazol-3-yl)carbazol-3-amine Chemical compound C1=CC=CC=C1N1C2=CC=C(N(C=3C=C4C5=CC=CC=C5N(C=5C=CC=CC=5)C4=CC=3)C=3C4=CC=CC=C4C=CC=3)C=C2C2=CC=CC=C21 COVCYOMDZRYBNM-UHFFFAOYSA-N 0.000 description 1
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- 150000007530 organic bases Chemical class 0.000 description 1
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- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
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- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 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
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- KBBSSGXNXGXONI-UHFFFAOYSA-N phenanthro[9,10-b]pyrazine Chemical compound C1=CN=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 KBBSSGXNXGXONI-UHFFFAOYSA-N 0.000 description 1
- 238000001296 phosphorescence spectrum Methods 0.000 description 1
- 238000001420 photoelectron spectroscopy Methods 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000002909 rare earth metal compounds Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000004544 sputter deposition Methods 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
- 239000000725 suspension Substances 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 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
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000002834 transmittance Methods 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
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- QGJSAGBHFTXOTM-UHFFFAOYSA-K trifluoroerbium Chemical compound F[Er](F)F QGJSAGBHFTXOTM-UHFFFAOYSA-K 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 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
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Classifications
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/72—Spiro hydrocarbons
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- 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
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
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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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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- C07C2603/96—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members
- C07C2603/97—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members containing five-membered rings
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Description
本実施の形態では、本発明の一態様である発光素子ついて図1乃至図3を用いて説明する。
本実施の形態では、本発明の一態様として、電荷発生層を挟んでEL層を複数有する構造の発光素子(以下、タンデム型発光素子という)について図4を用いて説明する。
本実施の形態では、本発明の一態様を適用した発光装置を用いた電子機器及び照明装置の一例について、図5及び図6を用いて説明する。
本実施例では、実施の形態1に記載のアントラセン化合物の一態様である、2’−(3,5−ジフェニル)フェニル−ジスピロ[9H−フルオレン−9,9’(10’H)−アントラセン−10’,9’’−(9H)フルオレン](略称:2mTPDfha)の合成例を具体的に例示する。なお、2mTPDfha(略称)の構造式(100)を以下に示す。
1H NMR(300MHz、CDCl3):δ(ppm)=6.40−6.45(m, 2H), 6.50(d, J=8.4Hz, 1H), 6.65(d, J=1.8Hz, 1H), 6.77−6.82(m, 2H), 7.08(dd, J=1.8Hz,8.3Hz, 1H), 7.25−7.50(m, 24H), 7.60(t, J=1.5Hz, 1H) , 7.90−7.96(m, 4H)
本実施例では、実施の形態1に記載のアントラセン化合物の一つである、9−(3−{ジスピロ[9H−フルオレン−9,9’(10’H)−アントラセン−10’,9’’−(9H)フルオレン]2’−イル}フェニル)−9H−カルバゾール(略称:2mCzPDfha)の合成例を具体的に例示する。なお、2mCzPDfha(略称)の構造式(103)を以下に示す。
1H NMR(300MHz、CDCl3):δ(ppm)=6.38−6.52(m, 3H), 6.64−6.69(m, 1H), 6.76−6.85(m, 2H), 7.04(dd, J=2.4Hz,8.4Hz, 1H), 7.09−7.17(m, 1H), 7.21−7.49(m, 21H), 7.93(d, J=7.2Hz, 4H), 8.10(d, J=7.8Hz, 2H)。
本実施例では、実施の形態1に記載のアントラセン化合物の一つである、2−(3−{ジスピロ[9H−フルオレン−9,9’(10’H)−アントラセン−10’,9’’−(9H)フルオレン]2’−イル}フェニル)ジベンゾ[f,h]キノキサリン(略称:2mDBqPDfha)の合成例を具体的に例示する。なお、2mDBqPDfha(略称)の構造式(112)を以下に示す。
まず、陽極1101として110nmの膜厚でケイ素を含むインジウム錫酸化物(ITSO)が成膜されたガラス基板を用意した。ITSO表面は、2mm角の大きさで表面が露出するよう周辺をポリイミド膜で覆い、電極面積は2mm×2mmとした。この基板上に発光素子を形成するための前処理として、基板表面を水で洗浄し、200℃で1時間焼成した後、UVオゾン処理を370秒行った。その後、10−4Pa程度まで内部が減圧された真空蒸着装置に基板を導入し、真空蒸着装置内の加熱室において170℃で30分間の真空焼成を行った後、基板を30分程度放冷した。
以上により得られた発光素子1を、窒素雰囲気のグローブボックス内において、発光素子が大気に曝されないように封止する作業を行った後、これらの発光素子1の動作特性について測定を行った。なお、測定は室温(25℃に保たれた雰囲気)で行った。
まず、陽極1101として110nmの膜厚でケイ素を含むインジウム錫酸化物(ITSO)が成膜されたガラス基板を用意した。ITSO表面は、2mm角の大きさで表面が露出するよう周辺をポリイミド膜で覆い、電極面積は2mm×2mmとした。この基板上に発光素子を形成するための前処理として、基板表面を水で洗浄し、200℃で1時間焼成した後、UVオゾン処理を370秒行った。その後、10−4Pa程度まで内部が減圧された真空蒸着装置に基板を導入し、真空蒸着装置内の加熱室において170℃で30分間の真空焼成を行った後、基板を30分程度放冷した。
以上により得られた発光素子2を、窒素雰囲気のグローブボックス内において、発光素子が大気に曝されないように封止する作業を行った後、これらの発光素子2の動作特性について測定を行った。なお、測定は室温(25℃に保たれた雰囲気)で行った。
まず、陽極1101として110nmの膜厚でケイ素を含むインジウム錫酸化物(ITSO)が成膜されたガラス基板を用意した。ITSO表面は、2mm角の大きさで表面が露出するよう周辺をポリイミド膜で覆い、電極面積は2mm×2mmとした。この基板上に発光素子を形成するための前処理として、基板表面を水で洗浄し、200℃で1時間焼成した後、UVオゾン処理を370秒行った。その後、10−4Pa程度まで内部が減圧された真空蒸着装置に基板を導入し、真空蒸着装置内の加熱室において170℃で30分間の真空焼成を行った後、基板を30分程度放冷した。
以上により得られた発光素子3を、窒素雰囲気のグローブボックス内において、発光素子が大気に曝されないように封止する作業を行った後、これらの発光素子3の動作特性について測定を行った。なお、測定は室温(25℃に保たれた雰囲気)で行った。
まず、陽極1101として110nmの膜厚でケイ素を含むインジウム錫酸化物(ITSO)が成膜されたガラス基板を用意した。ITSO表面は、2mm角の大きさで表面が露出するよう周辺をポリイミド膜で覆い、電極面積は2mm×2mmとした。この基板上に発光素子を形成するための前処理として、基板表面を水で洗浄し、200℃で1時間焼成した後、UVオゾン処理を370秒行った。その後、10−4Pa程度まで内部が減圧された真空蒸着装置に基板を導入し、真空蒸着装置内の加熱室において170℃で30分間の真空焼成を行った後、基板を30分程度放冷した。
発光層1104の他は、比較発光素子1と同様に作製した。発光層1104は、正孔輸送層1103上に、比較例のアントラセン化合物である2tBuDfha(略称)と、3,5−ビス[3−(9H−カルバゾール−9−イル)フェニル]ピリジン(略称:35DCzPPy)と、トリス[3−メチル−1−(2−メチルフェニル)−5−フェニル−1H−1,2,4−トリアゾラト]イリジウム(III)((略称:[Ir(Mptz1−mp)3])とを、2tBuDfha:35DCzPPy:[Ir(Mptz1−mp)3]=1:0.3:0.06(重量比)となるよう30nm蒸着した後、2−[3−(ジベンゾチオフェン−4−イル)フェニル]−1−フェニル−1H−ベンゾイミダゾール(略称:mDBTBIm−II)と、トリス[3−メチル−1−(2−メチルフェニル)−5−フェニル−1H−1,2,4−トリアゾラト]イリジウム(III)((略称:[Ir(Mptz1−mp)3)]とを、mDBTBIm−II:[Ir(Mptz1−mp)3]=1:0.06(重量比)となるように10nm蒸着して積層することにより形成した。
陽極1101と正孔注入層1107は、比較発光素子1と同様に作製した。
以上により得られた比較発光素子1、比較発光素子2および比較発光素子3を、窒素雰囲気のグローブボックス内において、発光素子が大気に曝されないように封止する作業を行った後、これらの比較発光素子1、比較発光素子2および比較発光素子3の動作特性について測定を行った。なお、測定は室温(25℃に保たれた雰囲気)で行った。
102 陰極
103 正孔輸送層
104 発光層
105 電子輸送層
106 EL層
107 正孔注入層
108 電子注入層
109 電荷発生層
201 アントラセン化合物
203 化合物
204a 化合物
204b 化合物
205 化合物
301 電極
302 EL層
304 電極
305 電荷発生層
1101 陽極
1102 陰極
1103 正孔輸送層
1104 発光層
1105 電子輸送層
1107 正孔注入層
1108 電子注入層
7100 テレビジョン装置
7101 筐体
7102 表示部
7103 スタンド
7111 リモコン操作機
7200 コンピュータ
7201 本体
7202 筐体
7203 表示部
7204 キーボード
7205 外部接続ポート
7206 ポインティングデバイス
7300 携帯型ゲーム機
7301a 筐体
7301b 筐体
7302 連結部
7303a 表示部
7303b 表示部
7304 スピーカ部
7305 記録媒体挿入部
7306 操作キー
7307 接続端子
7308 センサ
7400 携帯電話機
7401 筐体
7402 表示部
7403 操作ボタン
7404 外部接続ポート
7405 スピーカ
7406 マイク
7500 タブレット型端末
7501a 筐体
7501b 筐体
7502a 表示部
7502b 表示部
7503 軸部
7504 電源
7505 操作キー
7506 スピーカ
7601 照明装置
7602 照明装置
7603 卓上照明装置
7604 面状照明装置
7701 照明部
7703 支柱
7705 支持台
Claims (9)
- 陽極と、陰極の間に、
少なくとも正孔輸送層、発光層および電子輸送層を有し、
前記発光層は、下記一般式(G1)で表されるアントラセン化合物と、燐光を発する化合物と、を有し、
前記正孔輸送層および前記電子輸送層の少なくとも一は、下記一般式(G1)で表されるアントラセン化合物を有する発光素子。
但し、式中、αは、置換または無置換のm−フェニレン基または置換または無置換の3,3’−ビフェニルジイル基を表し、Arは、置換または無置換のフェニル基、置換または無置換のビフェニル基、置換または無置換のカルバゾリル基、置換または無置換のジベンゾチオフェニル基、置換または無置換のジベンゾフラニル基、置換または無置換のトリフェニレニル基、置換または無置換のナフチル基、置換または無置換のフェナントレニル基、置換または無置換のフルオレニル基、置換または無置換のピリジル基、置換または無置換のピリミジル基、置換または無置換のジベンゾキノキサリニル基、置換または無置換のベンゾイミダゾリル基、置換または無置換のベンゾオキサゾリル基のいずれかを表す。また、前記Arに置換基が結合している場合、前記置換基はフェニル基、ビフェニル基または炭素数1から6のアルキル基を表す。 - 陽極と、陰極の間に、
少なくとも正孔輸送層、発光層および電子輸送層を有し、
前記電子輸送層は、下記一般式(G1)で表されるアントラセン化合物と、電子輸送性の化合物と、を有する発光素子。
但し、式中、αは、置換または無置換のm−フェニレン基または置換または無置換の3,3’−ビフェニルジイル基を表し、Arは、置換または無置換のフェニル基、置換または無置換のビフェニル基、置換または無置換のカルバゾリル基、置換または無置換のジベンゾチオフェニル基、置換または無置換のジベンゾフラニル基、置換または無置換のトリフェニレニル基、置換または無置換のナフチル基、置換または無置換のフェナントレニル基、置換または無置換のフルオレニル基、置換または無置換のピリジル基、置換または無置換のピリミジル基、置換または無置換のジベンゾキノキサリニル基、置換または無置換のベンゾイミダゾリル基、置換または無置換のベンゾオキサゾリル基のいずれかを表す。また、前記Arに置換基が結合している場合、前記置換基はフェニル基、ビフェニル基または炭素数1から6のアルキル基を表す。 - 陽極と、陰極の間に、
少なくとも正孔輸送層、発光層および電子輸送層を有し、
前記正孔輸送層は、下記一般式(G1)で表されるアントラセン化合物と、正孔輸送性の化合物と、を有する発光素子。
但し、式中、αは、置換または無置換のm−フェニレン基または置換または無置換の3,3’−ビフェニルジイル基を表し、Arは、置換または無置換のフェニル基、置換または無置換のビフェニル基、置換または無置換のカルバゾリル基、置換または無置換のジベンゾチオフェニル基、置換または無置換のジベンゾフラニル基、置換または無置換のトリフェニレニル基、置換または無置換のナフチル基、置換または無置換のフェナントレニル基、置換または無置換のフルオレニル基、置換または無置換のピリジル基、置換または無置換のピリミジル基、置換または無置換のジベンゾキノキサリニル基、置換または無置換のベンゾイミダゾリル基、置換または無置換のベンゾオキサゾリル基のいずれかを表す。また、前記Arに置換基が結合している場合、前記置換基はフェニル基、ビフェニル基または炭素数1から6のアルキル基を表す。 - 陽極と、陰極の間に、
少なくとも正孔輸送層、発光層および電子輸送層を有し、
前記発光層は、下記一般式(G1)で表されるアントラセン化合物と、燐光を発する化合物と、を有し、
前記正孔輸送層は、下記一般式(G1)で表されるアントラセン化合物と、正孔輸送性の有機化合物と、を有し、
前記電子輸送層は、下記一般式(G1)で表されるアントラセン化合物と、電子輸送性の有機化合物と、を有する発光素子。
但し、式中、αは、置換または無置換のm−フェニレン基または置換または無置換の3,3’−ビフェニルジイル基を表し、Arは、置換または無置換のフェニル基、置換または無置換のビフェニル基、置換または無置換のカルバゾリル基、置換または無置換のジベンゾチオフェニル基、置換または無置換のジベンゾフラニル基、置換または無置換のトリフェニレニル基、置換または無置換のナフチル基、置換または無置換のフェナントレニル基、置換または無置換のフルオレニル基、置換または無置換のピリジル基、置換または無置換のピリミジル基、置換または無置換のジベンゾキノキサリニル基、置換または無置換のベンゾイミダゾリル基、置換または無置換のベンゾオキサゾリル基のいずれかを表す。また、前記Arに置換基が結合している場合、前記置換基はフェニル基、ビフェニル基または炭素数1から6のアルキル基を表す。 - 陽極と、陰極の間に、
少なくとも正孔輸送層、発光層および電子輸送層を有し、
前記発光層は、電子輸送性の有機化合物または正孔輸送性の有機化合物と、下記一般式(G1)で表されるアントラセン化合物と、燐光を発する化合物と、を有し、
前記正孔輸送層は、下記一般式(G1)で表されるアントラセン化合物と、正孔輸送性の有機化合物と、を有し、
前記電子輸送層は、下記一般式(G1)で表されるアントラセン化合物と、電子輸送性の有機化合物と、を有する発光素子。
但し、式中、αは、置換または無置換のm−フェニレン基または置換または無置換の3,3’−ビフェニルジイル基を表し、Arは、置換または無置換のフェニル基、置換または無置換のビフェニル基、置換または無置換のカルバゾリル基、置換または無置換のジベンゾチオフェニル基、置換または無置換のジベンゾフラニル基、置換または無置換のトリフェニレニル基、置換または無置換のナフチル基、置換または無置換のフェナントレニル基、置換または無置換のフルオレニル基、置換または無置換のピリジル基、置換または無置換のピリミジル基、置換または無置換のジベンゾキノキサリニル基、置換または無置換のベンゾイミダゾリル基、置換または無置換のベンゾオキサゾリル基のいずれかを表す。また、前記Arに置換基が結合している場合、前記置換基はフェニル基、ビフェニル基または炭素数1から6のアルキル基を表す。 - 請求項1乃至請求項5に記載の発光素子において、
燐光の発光波長のピークが570nm以下である発光素子。 - 構造式(100)で表される化合物。
- 構造式(103)で表される化合物。
- 構造式(112)で表される化合物。
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JP2018152563A (ja) * | 2013-03-28 | 2018-09-27 | 株式会社半導体エネルギー研究所 | 発光素子 |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101826581B1 (ko) | 2009-11-02 | 2018-02-07 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기금속 착체, 발광 소자, 표시 장치, 전자기기, 및 조명 장치 |
JP6230904B2 (ja) * | 2013-12-27 | 2017-11-15 | 株式会社半導体エネルギー研究所 | 有機化合物、発光素子 |
KR101837804B1 (ko) * | 2015-02-16 | 2018-03-12 | 주식회사 엘지화학 | 이중스피로형 화합물 및 이를 포함하는 유기 발광 소자 |
AU2016253217B2 (en) | 2015-04-24 | 2021-09-02 | Ajinomoto Co., Inc. | Method for secretory production of protein |
KR101826427B1 (ko) * | 2015-06-05 | 2018-02-06 | 주식회사 엘지화학 | 이중 스피로형 유기 화합물 및 이를 포함하는 유기 전자 소자 |
WO2017007213A2 (ko) * | 2015-07-07 | 2017-01-12 | 주식회사 엘지화학 | 이중스피로형 화합물 및 이를 포함하는 유기 발광 소자 |
TW202316695A (zh) | 2015-09-30 | 2023-04-16 | 日商半導體能源研究所股份有限公司 | 發光元件,顯示裝置,電子裝置,及照明裝置 |
KR101985649B1 (ko) * | 2015-10-07 | 2019-06-04 | 주식회사 엘지화학 | 이중 스피로형 화합물 및 이를 포함하는 유기 발광 소자 |
KR102000177B1 (ko) * | 2015-10-26 | 2019-07-16 | 주식회사 엘지화학 | 스피로형 화합물 및 이를 포함하는 유기 발광 소자 |
KR101984081B1 (ko) * | 2015-11-26 | 2019-05-31 | 주식회사 엘지화학 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
CN109790119B (zh) * | 2016-11-23 | 2022-11-04 | 广州华睿光电材料有限公司 | 有机化合物及其应用、有机混合物、有机电子器件 |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6998487B2 (en) * | 2001-04-27 | 2006-02-14 | Lg Chem, Ltd. | Double-spiro organic compounds and organic electroluminescent devices using the same |
KR100422914B1 (ko) * | 2001-04-27 | 2004-03-12 | 주식회사 엘지화학 | 이중 스피로형 유기물질을 함유하는 전기 소자 |
KR100428642B1 (ko) * | 2001-04-27 | 2004-04-27 | 주식회사 엘지화학 | 이중 스피로형 유기물질 |
CN1157461C (zh) | 2001-08-20 | 2004-07-14 | 清华大学 | 双螺环衍生物及其作为电致发光材料的应用 |
KR100497532B1 (ko) * | 2002-08-16 | 2005-07-01 | 네오뷰코오롱 주식회사 | 발광 스파이로 이합체 및 이를 포함하는 유기 발광 소자 |
CN101273008A (zh) * | 2005-09-30 | 2008-09-24 | 株式会社半导体能源研究所 | 螺芴衍生物,发光元件用材料,发光元件,发光设备和电子设备 |
US20070252517A1 (en) * | 2006-04-27 | 2007-11-01 | Eastman Kodak Company | Electroluminescent device including an anthracene derivative |
DE102009023156A1 (de) * | 2009-05-29 | 2010-12-02 | Merck Patent Gmbh | Polymere, die substituierte Indenofluorenderivate als Struktureinheit enthalten, Verfahren zu deren Herstellung sowie deren Verwendung |
JP2012020947A (ja) * | 2010-07-13 | 2012-02-02 | Canon Inc | 新規スピロ(アントラセン−9,9’−フルオレン)−10−オン化合物及びこれを有する有機発光素子 |
KR20120006811A (ko) * | 2010-07-13 | 2012-01-19 | 삼성모바일디스플레이주식회사 | 유기 발광 소자 |
KR101853875B1 (ko) * | 2011-06-22 | 2018-05-03 | 삼성디스플레이 주식회사 | 헤테로고리 화합물 및 이를 포함한 유기발광 소자 |
KR101512544B1 (ko) * | 2012-05-21 | 2015-04-15 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 발광 소자 |
US9478749B2 (en) * | 2013-03-28 | 2016-10-25 | Semiconductor Energy Laboratory Co., Ltd. | Anthracene compound, light-emitting element, light-emitting device, electronic appliance, and lighting device |
KR102230139B1 (ko) * | 2013-05-17 | 2021-03-18 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자, 조명 장치, 발광 장치, 및 전자 기기 |
KR101338499B1 (ko) | 2013-05-31 | 2013-12-10 | 김황호 | 공기조화장치 |
KR20160127692A (ko) * | 2015-04-27 | 2016-11-04 | 주식회사 엘지화학 | 이중스피로형 화합물 및 이를 포함하는 유기 발광 소자 |
KR101784606B1 (ko) * | 2015-04-27 | 2017-11-06 | 주식회사 엘지화학 | 이중스피로형 화합물 및 이를 포함하는 유기 발광 소자 |
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Cited By (1)
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JP2018152563A (ja) * | 2013-03-28 | 2018-09-27 | 株式会社半導体エネルギー研究所 | 発光素子 |
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US9478749B2 (en) | 2016-10-25 |
US20160163991A1 (en) | 2016-06-09 |
US10205100B2 (en) | 2019-02-12 |
KR20140118849A (ko) | 2014-10-08 |
KR102202474B1 (ko) | 2021-01-12 |
JP2014209603A (ja) | 2014-11-06 |
JP6502548B2 (ja) | 2019-04-17 |
US20170025616A1 (en) | 2017-01-26 |
JP2018152563A (ja) | 2018-09-27 |
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