JP6780925B2 - 発光素子、発光装置、電子機器及び照明装置 - Google Patents
発光素子、発光装置、電子機器及び照明装置 Download PDFInfo
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- JP6780925B2 JP6780925B2 JP2015142828A JP2015142828A JP6780925B2 JP 6780925 B2 JP6780925 B2 JP 6780925B2 JP 2015142828 A JP2015142828 A JP 2015142828A JP 2015142828 A JP2015142828 A JP 2015142828A JP 6780925 B2 JP6780925 B2 JP 6780925B2
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- 239000002096 quantum dot Substances 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000002909 rare earth metal compounds Chemical class 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 239000005060 rubber Substances 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
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 239000004575 stone Substances 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
- 238000001308 synthesis method Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 1
- HKCRVXUAKWXBLE-UHFFFAOYSA-N terbium(3+) Chemical compound [Tb+3] HKCRVXUAKWXBLE-UHFFFAOYSA-N 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
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 238000002834 transmittance Methods 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
- 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
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 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
- 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
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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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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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/40—Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
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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
- H10K85/30—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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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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
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
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- Y02E10/549—Organic PV cells
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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
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- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
Description
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。
本実施の形態では、発光素子に用いることができ、本発明の一態様であるジベンゾ[f,h]キノキサリン誘導体について説明する。
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)について説明する。なお、タンデム型発光素子は、図4(A)に示すように一対の電極(第1の電極401および第2の電極404)間に、複数のEL層(第1のEL層402(1)、第2のEL層402(2))を有する。
本実施の形態では、実施の形態1で説明した発光素子に着色層(カラーフィルタ等)を組み合わせる場合の発光装置の一態様について説明する。なお、本実施の形態では、発光装置の画素部の構成について図5を用いて説明する。
本実施の形態では、本発明の一態様であるジベンゾ[f,h]キノキサリン誘導体をEL層に用いた発光素子を有す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装置を適用して完成させた様々な電子機器の一例について、図7を用いて説明する。
本実施の形態では、本発明の一態様である発光装置を適用した照明装置の一例について、図9を用いて説明する。
本実施例では、本発明の一態様である合成方法として、2−{4−[3−(N−フェニル−9H−カルバゾール−3−イル)−9H−カルバゾール−9−イル]フェニル}ジベンゾ[f,h]キノキサリン(略称:2PCCzPDBq)(構造式(100))の合成方法について説明する。なお、2PCCzPDBqの構造を以下に示す。
まず、2−(4−クロロフェニル)ジベンゾ[f,h]キノキサリン1.0g(2.8mmol)、3−(9−フェニル−9H−カルバゾール−3−イル)−9H−カルバゾール1.1g(2.8mmol)、ナトリウム tert−ブトキシド0.54g(5.6mmol)、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(S−Phos)23mg(0.10mmol)を200mL三口フラスコに入れ混合し、フラスコを窒素置換した。この混合物に14mLのメシチレンを加え、フラスコ内を減圧下とし、攪拌することで脱気した。
本実施例では、本発明の一態様である合成方法として、2−{3−[3−(N−フェニル−9H−カルバゾール−3−イル)−9H−カルバゾール−9−イル]フェニル}ジベンゾ[f,h]キノキサリン(略称2mPCCzPDBq)(構造式(101))の合成方法について説明する。なお、2mPCCzPDBqの構造を以下に示す。
まず、2−(3−クロロフェニル)ジベンゾ[f,h]キノキサリン1.7g(5.0mmol)、3−(9−フェニル−9H−カルバゾール−3−イル)−9H−カルバゾール2.0g(5.0mmol)、ナトリウム tert−ブトキシド0.96g(10mmol)、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(S−Phos)41mg(0.10mmol)を200mL三口フラスコに入れ混合し、フラスコを窒素置換した。この混合物に25mLのメシチレンを加え、フラスコ内を減圧下とし、攪拌することで脱気した。
本実施例では、本発明の一態様である合成方法として、2−{4−[2−(N−フェニル−9H−カルバゾール−3−イル)−9H−カルバゾール−9−イル]フェニル}ジベンゾ[f,h]キノキサリン(略称:2PCCzPDBq−02)(構造式(102))の合成方法について説明する。なお、2PCCzPDBq−02の構造を以下に示す。
まず、2−(4−クロロフェニル)ジベンゾ[f,h]キノキサリン1.4g(4.2mmol)、2−(9−フェニル−9H−カルバゾール−3−イル)−9H−カルバゾール1.7g(4.2mmol)、ナトリウム tert−ブトキシド0.81g(8.4mmol)、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(S−Phos)34mg(0.10mmol)を200mL三口フラスコに入れ混合し、フラスコを窒素置換した。この混合物に21mLのメシチレンを加え、フラスコ内を減圧下とし、攪拌することで脱気した。
本実施例では、本発明の一態様である2−{3−[2−(N−フェニル−9H−カルバゾール−3−イル)−9H−カルバゾール−9−イル]フェニル}ジベンゾ[f,h]キノキサリン(略称2mPCCzPDBq−02)(構造式(103))の合成方法について説明する。なお、2mPCCzPDBq−02の構造を以下に示す。
まず、2−(3−クロロフェニル)ジベンゾ[f,h]キノキサリン1.7g(5.0mmol)、2−(9−フェニル−9H−カルバゾール−3−イル)−9H−カルバゾール2.0g(5.0mmol)、ナトリウム tert−ブトキシド0.96g(10mmol)、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(S−Phos)41mg(0.10mmol)を200mL三口フラスコに入れ混合し、フラスコを窒素置換した。この混合物に25mLのメシチレンを加え、フラスコ内を減圧下とし、攪拌することで脱気した。
まず、ガラス製の基板1100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より成膜し、陽極として機能する第1の電極1101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。
作製した発光素子1、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23〜図26に示す。
まず、ガラス製の基板1100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より成膜し、陽極として機能する第1の電極1101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。
作製した発光素子4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29〜図32に示す。
本実施例では、本発明の一態様である合成方法として、2−{3’−[3−(N−フェニル−9H−カルバゾール−3−イル)−9H−カルバゾール−9−イル]ビフェニル−3−イル}ジベンゾ[f,h]キノキサリン(略称2mPCCzBPDBq)(構造式(122))の合成方法について説明する。なお、2mPCCzBPDBqの構造を以下に示す。
まず、2−(3’−ブロモビフェニル−3−イル)ジベンゾ[f,h]キノキサリン2.0g(4.3mmol)、3−(9−フェニル−9H−カルバゾール−3−イル)−9H−カルバゾール1.8g(4.3mmol)、ナトリウム tert−ブトキシド0.83g(8.6mmol)、を100mL三口フラスコに入れ混合し、フラスコを窒素置換した。この混合物に22mLのメシチレンを加え、フラスコ内を減圧下とし、攪拌することで脱気した。
本実施例で作製した発光素子5、比較発光素子6、および比較発光素子7の素子構造を表6に示す。
作製した発光素子5、比較発光素子6、および比較発光素子7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。
本実施例で作製した発光素子8の素子構造を表9に示す。
作製した発光素子8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。
101 第1の有機化合物(h)
102 第2の有機化合物(a)
103 燐光性化合物(g)
104 正孔輸送層
105 正孔輸送性化合物(p)
201 第1の電極
202 EL層
203 第2の電極
211 正孔注入層
212 正孔輸送層
213 発光層
214 電子輸送層
215 電子注入層
401 第1の電極
402(1) 第1のEL層
402(2) 第2のEL層
402(n−1) 第(n−1)のEL層
402(n) 第(n)のEL層
404 第2の電極
405 電荷発生層
405(1) 第1の電荷発生層
405(2) 第2の電荷発生層
405(n−1) 第(n−1)の電荷発生層
501 基板
502 FET
503 第1の電極
504 隔壁
505 EL層
506R、506G、506B、506Y 発光領域
507R、507G、507B、507Y 発光素子
508R、508G、508B、508Y 着色層
509 黒色層(ブラックマトリクス)
510 第2の電極
511 封止基板
601 素子基板
602 画素部
603 駆動回路部(ソース線駆動回路)
604a、604b 駆動回路部(ゲート線駆動回路)
605 シール材
606 封止基板
607 配線
608 FPC(フレキシブルプリントサーキット)
609 FET
610 FET
611 スイッチング用FET
612 電流制御用FET
613 第1の電極(陽極)
614 絶縁物
615 EL層
616 第2の電極(陰極)
617 発光素子
618 空間
1100 基板
1101 第1の電極
1102 EL層
1103 第2の電極
1111 正孔注入層
1112 正孔輸送層
1113 発光層
1114 電子輸送層
1115 電子注入層
7100 テレビジョン装置
7101 筐体
7103 表示部
7105 スタンド
7107 表示部
7109 操作キー
7110 リモコン操作機
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
7302 筐体
7304 表示パネル
7305 時刻を表すアイコン
7306 その他のアイコン
7311 操作ボタン
7312 操作ボタン
7313 接続端子
7321 バンド
7322 留め金
7400 携帯電話機
7401 筐体
7402 表示部
7403 操作用ボタン
7404 外部接続部
7405 スピーカ
7406 マイク
7407 カメラ
8001 照明装置
8002 照明装置
8003 照明装置
8004 照明装置
9310 携帯情報端末
9311 表示パネル
9313 ヒンジ
9315 筐体
Claims (6)
- 陽極と、陰極と、の間にEL層を有し、
前記EL層は、発光層を有し、
前記発光層は、電子輸送性および正孔輸送性を有する第1の有機化合物と、正孔輸送性を有する第2の有機化合物と、発光物質と、を含み、
前記第1の有機化合物と前記第2の有機化合物は、励起錯体を形成する組み合わせであり、
前記第1の有機化合物のHOMO準位は、前記第2の有機化合物のHOMO準位よりも低く、
前記第1の有機化合物のHOMO準位と、前記第2の有機化合物のHOMO準位との差が、0.4eV以下である、発光素子。 - 陽極と、陰極と、の間にEL層を有し、
前記EL層は、発光層を有し、
前記発光層は、電子輸送性および正孔輸送性を有する第1の有機化合物と、正孔輸送性を有する第2の有機化合物と、発光物質と、を含み、
前記第1の有機化合物と前記第2の有機化合物は、励起錯体を形成する組み合わせであり、
前記第1の有機化合物のHOMO準位は、前記第2の有機化合物のHOMO準位よりも低く、
前記第1の有機化合物のHOMO準位と、前記第2の有機化合物のHOMO準位との差が、0.3eV以下である、発光素子。 - 請求項1または請求項2において、
前記発光物質は、燐光性化合物である、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発光素子を有する、発光装置。
- 請求項1乃至請求項3のいずれか一項に記載の発光素子、または、請求項4に記載の発光装置と、
接続端子、または、操作キーと、を有する電子機器。 - 請求項4に記載の発光装置と、筐体と、を有する照明装置。
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