JP7120759B2 - 発光素子、有機化合物、表示装置、電子機器、及び照明装置 - Google Patents
発光素子、有機化合物、表示装置、電子機器、及び照明装置 Download PDFInfo
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- JP7120759B2 JP7120759B2 JP2017244747A JP2017244747A JP7120759B2 JP 7120759 B2 JP7120759 B2 JP 7120759B2 JP 2017244747 A JP2017244747 A JP 2017244747A JP 2017244747 A JP2017244747 A JP 2017244747A JP 7120759 B2 JP7120759 B2 JP 7120759B2
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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
-
- 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
-
- 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
- C07D491/08—Bridged systems
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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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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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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
- 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
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- H—ELECTRICITY
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Description
本実施の形態では、例えば本発明の一態様に係る有機化合物及び発光素子について、以下説明する。
一般式(G0)乃至(G5)として表される化合物の具体的な構造としては、下記構造式(100)乃至(267)で表される化合物等を挙げることができる。なお、一般式(G0)乃至(G5)として表される化合物は、下記例示に限られない。
本実施の形態では、本発明の一態様に係る有機化合物である、一般式(G0)で表されるベンゾフロピラジン化合物、またはベンゾチエノピラジン化合物の合成方法について説明する。該化合物の合成方法としては、種々の反応を適用することができる。例えば、以下のような簡便な合成スキームにより一般式(G0)で表される化合物を合成できる。
実施の形態では、本発明の一態様の発光素子について、図1を用いて以下説明する。
まず、本発明の一態様の発光素子の構成について、図1(A)(B)(C)を用いて、以下説明する。
次に、発光層140の発光機構について、以下説明を行う。
・Host(141_1):有機化合物141_1(ホスト材料)
・Host(141_2):有機化合物141_2(ホスト材料)
・Guest(142):ゲスト材料142(燐光性化合物)
・SPH1:有機化合物141_1(ホスト材料)のS1準位
・TPH1:有機化合物141_1(ホスト材料)のT1準位
・SPH2:有機化合物141_2(ホスト材料)のS1準位
・TPH2:有機化合物141_2(ホスト材料)のT1準位
・SPG:ゲスト材料142(燐光性化合物)のS1準位
・TPG:ゲスト材料142(燐光性化合物)のT1準位
・SPE:励起錯体のS1準位
・TPE:励起錯体のT1準位
次に、本発明の一態様に係る発光素子の構成要素の詳細について、以下説明を行う。
発光層140中では、ホスト材料141が重量比で最も多く存在し、ゲスト材料142は、ホスト材料141中に分散される。ゲスト材料142が蛍光性化合物の場合、発光層140のホスト材料141(有機化合物141_1及び有機化合物141_2)のS1準位は、発光層140のゲスト材料(ゲスト材料142)のS1準位よりも高いことが好ましい。また、ゲスト材料142が燐光性化合物の場合、発光層140のホスト材料141(有機化合物141_1及び有機化合物141_2)のT1準位は、発光層140のゲスト材料(ゲスト材料142)のT1準位よりも高いことが好ましい。
正孔注入層111は、一対の電極の一方(電極101または電極102)からのホール注入障壁を低減することでホール注入を促進する機能を有し、例えば遷移金属酸化物、フタロシアニン化合物、あるいは芳香族アミンなどによって形成される。遷移金属酸化物としては、モリブデン酸化物やバナジウム酸化物、ルテニウム酸化物、タングステン酸化物、マンガン酸化物などが挙げられる。フタロシアニン化合物としては、フタロシアニンや金属フタロシアニンなどが挙げられる。芳香族アミンとしてはベンジジン化合物やフェニレンジアミン化合物などが挙げられる。ポリチオフェンやポリアニリンなどの高分子化合物を用いることもでき、例えば自己ドープされたポリチオフェンであるポリ(エチレンジオキシチオフェン)/ポリ(スチレンスルホン酸)などがその代表例である。
正孔輸送層112は正孔輸送性材料を含む層であり、正孔注入層111の材料として例示した正孔輸送性材料を使用することができる。正孔輸送層112は正孔注入層111に注入された正孔を発光層140へ輸送する機能を有するため、正孔注入層111のHOMO(Highest Occupied Molecular Orbital、最高被占軌道ともいう)準位と同じ、あるいは近いHOMO準位を有することが好ましい。
電子輸送層118は、電子注入層119を経て一対の電極の他方(電極101または電極102)から注入された電子を発光層140へ輸送する機能を有する。電子輸送性材料としては、正孔よりも電子の輸送性の高い材料を用いることができ、1×10-6cm2/Vs以上の電子移動度を有する材料であることが好ましい。電子を受け取りやすい化合物(電子輸送性を有する材料)としては、含窒素複素芳香族化合物のようなπ電子不足型複素芳香族化合物や金属錯体などを用いることができ、本発明の一態様に係る有機化合物はピラジン骨格を有するため、好適に用いることができる。他の具体例としては、発光層140に用いることができる電子輸送性材料として挙げたピリジン化合物、ビピリジン化合物、ピリミジン化合物、トリアジン化合物、キノキサリン化合物、ジベンゾキノキサリン化合物、フェナントロリン化合物、トリアゾール化合物、ベンゾイミダゾール化合物、オキサジアゾール化合物などが挙げられる。また、1×10-6cm2/Vs以上の電子移動度を有する物質であることが好ましい。なお、正孔よりも電子の輸送性の高い物質であれば、上記以外の物質を電子輸送層として用いても構わない。また、電子輸送層118は、単層だけでなく、上記物質からなる層が二層以上積層してもよい。
電子注入層119と電極102の界面における電子注入障壁を低減することで電子注入を促進する機能を有し、例えば第1族金属、第2族金属、あるいはこれらの酸化物、ハロゲン化物、炭酸塩などを用いることができる。また、先に示す電子輸送性材料と、これに対して電子供与性を示す材料の複合材料を用いることもできる。電子供与性を示す材料としては、第1族金属、第2族金属、あるいはこれらの酸化物などを挙げることができる。具体的には、フッ化リチウム(LiF)、フッ化ナトリウム(NaF)、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119にエレクトライドを用いてもよい。該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。また、電子注入層119に、電子輸送層118で用いることが出来る物質を用いても良い。
量子ドットは、数nmから数十nmサイズの半導体ナノ結晶であり、1×103個から1×106個程度の原子から構成されている。量子ドットはサイズに依存してエネルギーシフトするため、同じ物質から構成される量子ドットであっても、サイズによって発光波長が異なる。そのため、用いる量子ドットのサイズを変更することによって、容易に発光波長を変更することができる。
電極101及び電極102は、発光素子の陽極または陰極としての機能を有する。電極101及び電極102は、金属、合金、導電性化合物、及びこれらの混合物や積層体などを用いて形成することができる。
また、本発明の一態様に係る発光素子は、ガラス、プラスチックなどからなる基板上に作製すればよい。基板上に作製する順番としては、電極101側から順に積層しても、電極102側から順に積層しても良い。
本実施の形態においては、実施の形態3に示す発光素子の構成と異なる構成の発光素子、について、図2を用いて、以下説明を行う。なお、図2において、図1(A)に示す符号と同様の機能を有する箇所には、同様のハッチパターンとし、符号を省略する場合がある。また、同様の機能を有する箇所には、同様の符号を付し、その詳細な説明は省略する場合がある。
図2は、発光素子250の断面模式図である。
図3(A)は、発光装置を示す上面図、図3(B)は図3(A)をA-B及びC-Dで切断した断面図である。この発光装置は、発光素子の発光を制御するものとして、点線で示された駆動回路部(ソース側駆動回路)601、画素部602、駆動回路部(ゲート側駆動回路)603を含んでいる。また、604は封止基板、625は乾燥材、605はシール材であり、シール材605で囲まれた内側は、空間607になっている。
図4には発光装置の一例として、白色発光を呈する発光素子を形成し、着色層(カラーフィルタ)を形成した発光装置の例を示す。
トップエミッション型の発光装置の断面図を図5に示す。この場合、基板1001は光を通さない基板を用いることができる。TFTと発光素子の陽極とを接続する接続電極を作製するまでは、ボトムエミッション型の発光装置と同様に形成する。その後、第3の層間絶縁膜1037を電極1022を覆って形成する。この絶縁膜は平坦化の役割を担っていても良い。第3の層間絶縁膜1037は第2の層間絶縁膜1021と同様の材料の他、他の様々な材料を用いて形成することができる。
本実施の形態では、本発明の一態様の電子機器について説明する。
本実施の形態では、本発明の一態様の発光素子を様々な電子機器、照明装置に適用する一例について、図8及び図9を用いて説明する。
<ステップ1; 6-クロロ-3-(5-クロロ-2-メトキシフェニル)ピラジン-2-アミンの合成>
3-ブロモ-6-クロロピラジン-2-アミン1.00gと5-クロロ-2-メトキシフェニルボロン酸0.90g、フッ化カリウム0.93g、テトラヒドロフラン17mL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)0.088g、トリ-t-ブチルホスフィン0.8mLを加え、80℃で40時間撹拌することで反応させた。所定時間経過後、得られた混合物を吸引ろ過し、ろ液を濃縮した。得られた残差を、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、得られたろ液を濃縮することで、目的物である6-クロロ-3-(5-クロロ-2-メトキシフェニル)ピラジン-2-アミンの黄白色粉末を0.92g、収率71%で得た。ステップ1の合成スキームを下記(a-1)に示す。
上記ステップ1で得た6-クロロ-3-(5-クロロ-2-メトキシフェニル)ピラジン-2-アミン1.37gと脱水テトラヒドロフラン16mL、氷酢酸32mLを三口フラスコに入れ、内部を窒素置換した。フラスコを-10℃に冷却した後、亜硝酸tert-ブチル1.9mLを滴下し、-10℃で1時間、0℃で20時間攪拌した。所定時間経過後、得られた懸濁液に水100mLを加え、吸引ろ過した。得られた固体を、ジクロロメタンに溶かし、セライト、アルミナ、セライトの順に積層したろ過補助剤を用いてろ過し、ろ液を濃縮することにより、目的物である3,8-ジクロロベンゾフロ[2,3-b]ピラジンの白色固体を0.87g、収率70%で得た。ステップ2の合成スキームを下記(a-2)に示す。
さらに、上記ステップ2で得た3,8-ジクロロベンゾフロ[2,3-b]ピラジン0.87g、3-(4-ジベンゾチオフェン)フェニルボロン酸2.41g、リン酸三カリウム4.57g、ジグリム29mL、tert-ブタノール2.0mLを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、酢酸パラジウム(II)0.016g、ジ(1-アダマンチル)-n-ブチルホスフィン(略称:CataCXiumA)0.054gを加え、140℃で8時間撹拌し、反応させた。所定時間経過後、得られた懸濁液を吸引ろ過し、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で精製した後、トルエンとヘキサンの混合溶媒にて再結晶することにより、目的物である、3,8mDBtP2Bfprの黄白色固体を1.25g、収率52%で得た。ステップ3の合成スキームを下記(a-3)に示す。
<ステップ1;5-クロロ-3-(5-クロロ-2-メトキシフェニル)ピラジン-2-アミンの合成>
3-ブロモ-5-クロロピラジン-2-アミン2.48gと5-クロロ-2-メトキシフェニルボロン酸2.19g、フッ化カリウム2.26g、テトラヒドロフラン43mL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)0.44g、トリ-t-ブチルホスフィン4.0mLを加え、80℃で42時間撹拌することで反応させた。所定時間経過後、得られた混合物を吸引ろ過し、ろ液を濃縮した。得られた残差を、トルエン:酢酸エチル=10:1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、目的物である2,8-ビス[3-(ジベンゾチオフェン-4-イル)フェニル]ベンゾフロ[2,3-b]ピラジン1.00g、収率31%で得た。ステップ1の合成スキームを下記(b-1)に示す。
次に、上記ステップ1で得た5-クロロ-3-(5-クロロ-2-メトキシフェニル)ピラジン-2-アミン1.00gと脱水テトラヒドロフラン12mL、氷酢酸24mLを三口フラスコに入れ、内部を窒素置換した。フラスコを-10℃に冷却した後、亜硝酸tert-ブチル1.3mLを滴下し、-10℃で1時間、0℃で20時間攪拌した。所定時間経過後、得られた懸濁液に水100mLを加え、吸引ろ過した。得られた固体を、ジクロロメタンを展開溶媒に用いたシリカゲルカラムクロマトグラフィーにより精製し、目的物である2,8-ジクロロベンゾフロ[2,3-b]ピラジンを0.66g、収率75%で得た。ステップ2の合成スキームを下記(b-2)に示す。
上記ステップ2で得た2,8-ジクロロベンゾフロ[2,3-b]ピラジン0.66g、3-(4-ジベンゾチオフェン)フェニルボロン酸1.90g、リン酸三カリウム3.59g、ジグリム23mL、tert-ブタノール1.6mLを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、酢酸パラジウム(II)0.026g、ジ(1-アダマンチル)-n-ブチルホスフィン(略称:CataCXiumA)0.086gを加え、140℃で15時間撹拌し、反応させた。所定時間経過後、得られた懸濁液を吸引ろ過し、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で精製した後、トルエンとヘキサンの混合溶媒にて再結晶することにより、目的物である2,8mDBtP2Bfprの白色固体を0.61g、収率32%で得た。ステップ3の合成スキームを下記(b-3)に示す。
次に、トルエン溶液中の2,8mDBtP2Bfpr吸収スペクトル及び発光スペクトルを図14に示す。なお、トルエン溶液中における2,8mDBtP2Bfprの吸収スペクトル及び発光スペクトルの測定方法は、実施例1と同様である。
基板200上に電極101として、ITSO膜を厚さが70nmになるように形成した。なお、電極101の電極面積は、4mm2(2mm×2mm)とした。
作製した発光素子1の電流効率-輝度特性を図15に示す。また、電流密度-電圧特性を図16に示す。また、外部量子効率-輝度特性を図17に示す。なお、発光素子1の測定は室温(23℃に保たれた雰囲気)で行った。また、発光素子1に2.5mA/cm2の電流密度で電流を流した際の電界発光スペクトルを図18に示す。なお、測定は室温で行った。
次に、発光素子1の2mAにおける定電流駆動試験を行った。その結果を図19に示す。図19から分かるように発光素子1の輝度半減寿命は1000時間を超えており、発光素子1は非常に高い信頼性を有していることが分かった。
基板200上に電極101として、ITSO膜を厚さが70nmになるように形成した。なお、電極101の電極面積は、4mm2(2mm×2mm)とした。
作製した発光素子2の電流効率-輝度特性を図20に示す。また、電流密度-電圧特性を図21に示す。また、外部量子効率-輝度特性を図22に示す。なお、発光素子2の測定は室温(23℃に保たれた雰囲気)で行った。また、発光素子2に2.5mA/cm2の電流密度で電流を流した際の電界発光スペクトルを図23に示す。なお、測定は室温で行った。
次に、発光素子2の2mAにおける定電流駆動試験を行った。その結果を図24に示す。図24から分かるように発光素子2の輝度半減寿命は350時間を超えており、発光素子2は高い信頼性を有していることが分かった。
101 電極
102 電極
106 発光ユニット
110 発光ユニット
111 正孔注入層
112 正孔輸送層
113 電子輸送層
114 電子注入層
115 電荷発生層
116 正孔注入層
117 正孔輸送層
118 電子輸送層
119 電子注入層
120 発光層
130 発光層
140 発光層
141 ホスト材料
141_1 有機化合物
141_2 有機化合物
142 ゲスト材料
150 発光素子
170 発光層
200 基板
220 基板
250 発光素子
601 ソース側駆動回路
602 画素部
603 ゲート側駆動回路
604 封止基板
605 シール材
607 空間
608 配線
610 素子基板
611 スイッチング用TFT
612 電流制御用TFT
613 電極
614 絶縁物
616 EL層
617 電極
618 発光素子
623 nチャネル型TFT
624 pチャネル型TFT
900 携帯情報端末
901 筐体
902 筐体
903 表示部
905 ヒンジ部
910 携帯情報端末
911 筐体
912 表示部
913 操作ボタン
914 外部接続ポート
915 スピーカ
916 マイク
917 カメラ
920 カメラ
921 筐体
922 表示部
923 操作ボタン
924 シャッターボタン
926 レンズ
1001 基板
1002 下地絶縁膜
1003 ゲート絶縁膜
1006 ゲート電極
1007 ゲート電極
1008 ゲート電極
1020 層間絶縁膜
1021 層間絶縁膜
1022 電極
1024B 電極
1024G 電極
1024R 電極
1024W 電極
1025B 下部電極
1025G 下部電極
1025R 下部電極
1025W 下部電極
1026 隔壁
1028 EL層
1029 電極
1031 封止基板
1032 シール材
1033 基材
1034B 着色層
1034G 着色層
1034R 着色層
1035 黒色層
1036 オーバーコート層
1037 層間絶縁膜
1040 画素部
1041 駆動回路部
1042 周辺部
3500 多機能端末
3502 筐体
3504 表示部
3506 カメラ
3508 照明
3600 ライト
3602 筐体
3608 照明
3610 スピーカ
8501 照明装置
8502 照明装置
8503 照明装置
8504 照明装置
9000 筐体
9001 表示部
9003 スピーカ
9005 操作キー
9006 接続端子
9007 センサ
9008 マイクロフォン
9055 ヒンジ
9200 携帯情報端末
9201 携帯情報端末
9202 携帯情報端末
Claims (9)
- 一対の電極間にベンゾフロピラジン骨格を有する物質を含み、
前記ベンゾフロピラジン骨格におけるベンゼン環は、総炭素数6以上100以下の第一の置換基を有し、
前記第一の置換基は、フェニレン基を介してジベンゾチオフェン環が結合した構造を有し、
前記ベンゾフロピラジン骨格におけるピラジン環は、総炭素数6以上100以下の第二の置換基を有し、
前記第二の置換基は、フェニレン基を介してπ電子過剰型のジベンゾチオフェン環が結合した構造を有する発光素子。 - 一対の電極間にベンゾフロピラジン骨格を有する物質を含み、
前記ベンゾフロピラジン骨格におけるベンゼン環は、総炭素数6以上100以下の第一の置換基を有し、
前記第一の置換基は、フェニレン基を介して、ジベンゾチオフェン環が結合した構造を有し、
前記ベンゾフロピラジン骨格におけるピラジン環は、総炭素数6以上100以下の第二の置換基を有し、
前記第二の置換基は、フェニレン基を介して、ジベンゾチオフェン環が結合した構造を有する発光素子。 - 請求項1または請求項2において、
前記ベンゾフロピラジン骨格を有する物質と三重項励起エネルギーを発光に変換できる物質とを含む発光層を有する発光素子。 - 請求項1または請求項2において、
前記ベンゾフロピラジン骨格を有する物質と燐光性化合物とを含む発光層を有する発光素子。 - 請求項5に記載の有機化合物を用いた発光素子。
- 請求項1乃至請求項4、及び請求項6のいずれか一項に記載の発光素子と、
カラーフィルタ及びトランジスタの少なくとも一と、
を有する表示装置。 - 請求項7に記載の表示装置と、
筐体及びタッチセンサの少なくとも一と、
を有する電子機器。 - 請求項1乃至請求項4、及び請求項6のいずれか一項に記載の発光素子と、
筐体及びタッチセンサの少なくとも一と、
を有する照明装置。
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