JPWO2012050002A1 - 含窒素芳香族化合物、有機半導体材料及び有機電子デバイス - Google Patents
含窒素芳香族化合物、有機半導体材料及び有機電子デバイス Download PDFInfo
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- JPWO2012050002A1 JPWO2012050002A1 JP2012538638A JP2012538638A JPWO2012050002A1 JP WO2012050002 A1 JPWO2012050002 A1 JP WO2012050002A1 JP 2012538638 A JP2012538638 A JP 2012538638A JP 2012538638 A JP2012538638 A JP 2012538638A JP WO2012050002 A1 JPWO2012050002 A1 JP WO2012050002A1
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Images
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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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- 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
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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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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- 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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- 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
- 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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- 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
- 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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- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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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
- 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
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Abstract
Description
本発明の有機EL素子は、基板に支持されていることが好ましい。この基板については、特に制限はなく、従来から有機EL素子に慣用されているものであればよく、例えば、ガラス、透明プラスチック、石英などからなるものを用いることができる。
有機EL素子における陽極としては、仕事関数の大きい(4eV以上)金属、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが好ましく用いられる。このような電極物質の具体例としてはAu等の金属、CuI、インジウムチンオキシド(ITO)、SnO2、ZnO等の導電性透明材料が挙げられる。また、IDIXO(In2O3−ZnO)等非晶質で透明導電膜を作製可能な材料を用いてもよい。陽極はこれらの電極物質を蒸着やスパッタリング等の方法により、薄膜を形成させ、フォトリソグラフィー法で所望の形状のパターンを形成してもよく、あるいはパターン精度をあまり必要としない場合は(100μm以上程度)、上記電極物質の蒸着やスパッタリング時に所望の形状のマスクを介してパターンを形成してもよい。あるいは、有機導電性化合物のように塗布可能な物質を用いる場合には、印刷方式、コーティング方式等湿式成膜法を用いることもできる。この陽極より発光を取り出す場合には、透過率を10%より大きくすることが望ましく、また陽極としてのシート抵抗は数百Ω/□以下が好ましい。更に膜厚は材料にもよるが、通常10〜1000nm、好ましくは10〜200nmの範囲で選ばれる。
一方、陰極としては、仕事関数の小さい(4eV以下)金属(電子注入性金属と称する)、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが用いられる。このような電極物質の具体例としては、ナトリウム、ナトリウム−カリウム合金、マグネシウム、リチウム、マグネシウム/銅混合物、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、インジウム、リチウム/アルミニウム混合物、希土類金属等が挙げられる。これらの中で、電子注入性及び酸化等に対する耐久性の点から、電子注入性金属とこれより仕事関数の値が大きく安定な金属である第二金属との混合物、例えば、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、リチウム/アルミニウム混合物、アルミニウム等が好適である。陰極はこれらの電極物質を蒸着やスパッタリング等の方法により薄膜を形成させることにより、作製することができる。また、陰極としてのシート抵抗は数百Ω/□以下が好ましく、膜厚は通常10nm〜5μm、好ましくは50〜200nmの範囲で選ばれる。なお、発光した光を透過させるため、有機EL素子の陽極又は陰極のいずれか一方が、透明又は半透明であれば発光輝度が向上し好都合である。
発光層は蛍光発光層、燐光発光層のいずれでも良いが、燐光発光層であることが好ましい。
注入層とは、駆動電圧低下や発光輝度向上のために電極と有機層間に設けられる層のことで、正孔注入層と電子注入層があり、陽極と発光層又は正孔輸送層の間、及び陰極と発光層又は電子輸送層との間に存在させてもよい。注入層は必要に応じて設けることができる。注入材料としては、一般式(1)で表される本発明の化合物を用いることができるが、該化合物を他の何れかの有機層に使用する場合は、従来公知の化合物の中から任意のものを選択して用いることができる。
正孔阻止層とは広い意味では電子輸送層の機能を有し、電子を輸送する機能を有しつつ正孔を輸送する能力が著しく小さい正孔阻止材料からなり、電子を輸送しつつ正孔を阻止することで電子と正孔の再結合確率を向上させることができる。
電子阻止層とは、正孔を輸送する機能を有しつつ電子を輸送する能力が著しく小さい材料から成り、正孔を輸送しつつ電子を阻止することで電子と正孔が再結合する確率を向上させることができる。
励起子阻止層とは、発光層内で正孔と電子が再結合することにより生じた励起子が電荷輸送層に拡散することを阻止するための層であり、本層の挿入により励起子を効率的に発光層内に閉じ込めることが可能となり、素子の発光効率を向上させることができる。励起子阻止層は発光層に隣接して陽極側、陰極側のいずれにも挿入することができ、両方同時に挿入することも可能である。
正孔輸送層とは正孔を輸送する機能を有する正孔輸送材料からなり、正孔輸送層は単層又は複数層設けることができる。
電子輸送層とは電子を輸送する機能を有する材料からなり、電子輸送層は単層又は複数層設けることができる。
基板は、特に限定されず、例えば、従来公知の構成とすることができる。基板としては、例えば、ガラス(例えば、石英ガラス)、シリコン、セラミック、プラスチックが挙げられる。プラスチックとしては、例えば、ポリエチレンテレフタレート、ポリエチレンナフタレート、ポリカーボネート等の汎用の樹脂基板が挙げられる。樹脂基板は、酸素、水蒸気等のガスの透過性を低くするためのガスバリア膜を積層したものであることが好ましい。
ゲート電極は、特に限定されず、例えば、従来公知の構成とすることができる。ゲート電極としては、例えば、金、白金、クロム、タングステン、タンタル、ニッケル、銅、アルミニウム、銀、マグネシウム、カルシウム等の金属またはそれらの合金、ポリシリコン、アモルファスシリコン、グラファイト、ITO、酸化亜鉛、導電性ポリマー等の材料を用いることができる。
ゲート絶縁層は、特に限定されず、例えば、従来公知の構成とすることができる。ゲート絶縁層としては、SiO2、Si3N4、SiON、Al2O3、Ta2O5、アモルファスシリコン、ポリイミド樹脂、ポリビニルフェノール樹脂、ポリパラキシリレン樹脂、ポリメチルメタクリレート樹脂、フッ素樹脂(PTFE、PFA、PETFE、PCTFE、CYTOP(登録商標)等)等の材料を用いることができる。
有機半導体層は、本発明の化合物を含む層であれば、特に限定されない。例えば、実質的に本発明の化合物のみからなる層であってもよく、本発明の化合物以外の他の物質を含有する層であってもよい。
ソース電極およびドレイン電極は、いずれも特に限定されず、例えば、従来公知の構成とすることができる。ソース電極およびドレイン電極としては、いずれも、金、白金、クロム、タングステン、タンタル、ニッケル、銅、アルミニウム、銀、マグネシウム、カルシウム等の金属またはそれらの合金、ポリシリコン、アモルファスシリコン、グラファイト、ITO、酸化亜鉛、導電性ポリマー等の材料を用いることができる。
基板は、特に限定されず、例えば、従来公知の構成とすることができる。機械的、熱的強度を有し、透明性を有するガラス基板や透明性樹脂フィルムを使用することが好ましい。透明性樹脂フィルムとしては、ポリエチレン、エチレン−酢酸ビニル共重合体、エチレン−ビニルアルコール共重合体、ポリプロピレン、ポリスチレン、ポリメチルメタアクリレート、ポリ塩化ビニル、ポリビニルアルコール、ポリビニルブチラール、ナイロン、ポリエーテルエーテルケトン、ポリサルホン、ポリエーテルサルフォン、テトラフルオロエチレン−パーフルオロアルキルビニルエーテル共重合体、ポリビニルフルオライド、テトラフルオロエチレン−エチレン共重合体、テトラフルオロエチレン−ヘキサフルオロプロピレン共重合体、ポリクロロトリフルオロエチレン、ポリビニリデンフルオライド、ポリエステル、ポリカーボネート、ポリウレタン、ポリイミド、ポリエーテルイミド、ポリイミド、ポリプロピレン等が挙げられる。
電極材料としては、一方の電極には仕事関数の大きな導電性素材、もう一方の電極には仕事関数の小さな導電性素材を使用することが好ましい。仕事関数の大きな導電性素材を用いた電極は正極となる。この仕事関数の大きな導電性素材としては金、白金、クロム、ニッケルなどの金属のほか、透明性を有するインジウム、スズなどの金属酸化物、複合金属酸化物(インジウム錫酸化物(ITO)、インジウム亜鉛酸化物(IZO)など)が好ましく用いられる。ここで、正極に用いられる導電性素材は、有機半導体層とオーミック接合するものであることが好ましい。さらに、後述する正孔輸送層を用いた場合においては、正極に用いられる導電性素材は正孔輸送層とオーミック接合するものであることが好ましい。
有機半導体層は本発明の化合物を含む。すなわち、一般式(1)で表される本発明の化合物を含む電子供与性有機材料および電子受容性有機材料を含む。これらの材料は混合されていることが好ましく、電子供与性有機材料と電子受容性有機材料が分子レベルで相溶しているか、相分離していることが好ましい。この相分離構造のドメインサイズは特に限定されるものではないが通常1nm以上50nm以下のサイズである。また、電子供与性有機材料と電子受容性有機材料が積層されている場合は、p型半導体特性を示す電子供与性有機材料を有する層が正極側、n型半導体特性を示す電子受容性有機材料を有する層が負極側であることが好ましい。有機半導体層は5nm〜500nmの厚さが好ましく、より好ましくは30nm〜300nmである。積層されている場合は、本発明の電子供与性有機材料を有する層は上記厚さのうち1nm〜400nmの厚さを有していることが好ましく、より好ましくは15nm〜150nmである。
APCI-TOFMS, m/z 791 [M+H]+
APCI-TOFMS, m/z 969 [M+H]+、1H-NMR測定結果(測定溶媒:THF-d8)を図6に示す。
APCI-TOFMS, m/z 599 [M+H]+
APCI-TOFMS, m/z 974 [M+H]+
APCI-TOFMS, m/z 640 [M+H]+
APCI-TOFMS, m/z 718 [M+H]+
APCI-TOFMS, m/z 717 [M+H]+、1H-NMR測定結果(測定溶媒:THF-d8)を図7に示す。
APCI-TOFMS, m/z 806 [M+H]+
APCI-TOFMS, m/z 871 [M+H]+
APCI-TOFMS, m/z 661 [M+H]+
APCI-TOFMS, m/z 561 [M+H]+
APCI-TOFMS, m/z 564 [M+H]+
APCI-TOFMS, m/z 1148 [M+H]+
膜厚110 nmのITOからなる陽極が形成されたガラス基板上に、各薄膜を真空蒸着法にて、真空度4.0×10-5 Paで積層した。まず、ITO上に銅フタロシアニン(CuPC)を25 nmの厚さに形成した。次に、正孔輸送層として4,4'-ビス[N-(1-ナフチル)-N-フェニルアミノ]ビフェニル(NPB)を40 nmの厚さに形成した。次に、正孔輸送層上に、ホスト材料として実施例1で得た化合物1−2と、燐光発光ドーパントとしてのトリス(2‐フェニルピリジン)イリジウム(III)(Ir(ppy)3)とを異なる蒸着源から、共蒸着し、40 nmの厚さに発光層を形成した。発光層中のIr(ppy)3の濃度は10.0 wt%であった。次に、電子輸送層としてトリス(8−ヒドロキシキノリナト)アルミニウム(III)(Alq3)を20 nmの厚さに形成した。更に、電子輸送層上に、電子注入層としてフッ化リチウム(LiF)を1.0 nmの厚さに形成した。最後に、電子注入層上に、電極としてアルミニウム(Al)を70 nmの厚さに形成し、有機EL素子を作製した。
発光層のホスト材料として、化合物1−7を用いた以外は実施例15と同様にして有機EL素子を作製した。
発光層のホスト材料として、化合物1−8を用いた以外は実施例15と同様にして有機EL素子を作製した。
発光層のホスト材料として、化合物1−24を用いた以外は実施例15と同様にして有機EL素子を作製した。
発光層のホスト材料として、化合物1−34を用いた以外は実施例15と同様にして有機EL素子を作製した。
発光層のホスト材料として、化合物1−49を用いた以外は実施例15と同様にして有機EL素子を作製した。
発光層のホスト材料として、化合物1−58を用いた以外は実施例15と同様にして有機EL素子を作製した。
発光層のホスト材料として、4,4'-ビス(9-カルバゾリル)ビフェニル(CBP)を用いた以外は実施例15と同様にして有機EL素子を作製した。
膜厚110 nmのITOからなる陽極が形成されたガラス基板上に、各薄膜を真空蒸着法にて、真空度4.0×10-5 Paで積層した。まず、ITO上に銅フタロシアニン(CuPC)を25 nmの厚さに形成した。次に、正孔輸送層としてNPBを55 nmの厚さに形成した。次に、正孔輸送層上に、ホスト材料としての実施例6で得た化合物1−39と、燐光発光ドーパントとしてのビス(2-(2'-ベンゾ[4,5-a]チエニル)ピリジナト-N,C3)イリジウム(アセチルアセトネート)〔(Btp)2Iracac〕とを異なる蒸着源から、共蒸着し、47.5 nmの厚さに発光層を形成した。発光層中の(Btp)2Iracacの濃度は8.0 wt%であった。次に、電子輸送層としてAlq3を30 nmの厚さに形成した。更に、電子輸送層上に、電子注入層としてLiFを1.0 nmの厚さに形成した。最後に、電子注入層上に、電極としてAlを200 nmの厚さに形成し、有機EL素子を作製した。
発光層のホスト材料として、化合物1−41を用いた以外は実施例22と同様にして有機EL素子を作製した。
発光層のホスト材料として、化合物1−53を用いた以外は実施例22と同様にして有機EL素子を作製した。
発光層のホスト材料として、化合物2−11を用いた以外は実施例22と同様にして有機EL素子を作製した。
発光層のホスト材料として、ビス(2-メチル-8-キノリノラト)-4-フェニルフェノラトアルミニウム(III)(BAlq)を用いた以外は実施例22と同様にして有機EL素子を作製した。
図2に示す構成の有機TFT素子を作製し、本発明の有機半導体材料の特性を評価した。まず、約300 nmの厚みの熱成長酸化ケイ素層を有するシリコンウェハ(nドープ)を、硫酸−過酸化水素水溶液で洗浄し、イソプロピルアルコールで煮沸した後、乾燥した。得られたシリコンウェハにフォトレジストをスピンコート後、フォトマスクを介して露光機により露光した。次いで、現像液で現像を行った後、イオン交換水で洗浄し、空気乾燥した。そのパターニングされたフォトレジストが塗布されたシリコンウェハ上に、真空蒸着法により、厚さ3 nmのクロム、更にその上に50 nmの金を蒸着した。そのシリコンウェハを、リムーバー溶液に浸すことでシリコンウェハ上にソース電極およびドレイン電極を作製した。ソース電極およびドレイン電極が作製されたシリコンウェハをアセトンで洗浄し、さらに、イソプロピルアルコールで煮沸し乾燥した後、オクチルトリクロロシランの約1×10-6M トルエン溶液中に、一晩浸漬した。その後、トルエン、イソプロピルアルコールで洗浄した後、110 ℃で約10 分間加熱することで、オクチルトリクロロシラン(OTS)処理を行った有機TFT基板を作製した。チャネル長はL=25 μm、チャネル幅はW=15.6 μmであった。次に化合物1−2のクロロベンゼン溶液(1重量%)を0.2 μmのシリンジフィルターを用いてろ過し、OTS処理を行った基板上に、室温、1000 rpm、30 秒間の条件でスピンコートした。次いでそれを80 ℃で30 分間乾燥した。この時、有機半導体層の厚さは50 nmであった。このようにして図2に示す構造を有する有機TFT素子を得た。
Id=(W/2L)μCi(Vg−Vt)2 (I)
実施例25において、化合物1−2のクロロベンゼン溶液(1重量%)の代わりに、化合物1−8のクロロホルム溶液(1重量%)を使用し、室温にて1000 rpm、30 秒の条件でスピンコートを行ったほかは同様の操作を行い、有機TFT素子を作製した。得られた有機TFT素子の特性を表3に示す。
実施例25と同様の方法により、有機TFT基板を作製した。チャネル長はL=25 μm、チャネル幅はW=15.6μmであった。次に、有機TFT基板上に真空蒸着法にて、真空度5.0×10-4Pa の条件にて化合物3−6を蒸着し、化合物3−6の薄膜を0.3 nm/秒にて100 nmの厚さで形成する事により、図2に示す構造を有する有機TFT素子を得た。得られた有機TFT素子の特性を表3に示す。
Claims (9)
- 一般式(1)で表される含窒素芳香族化合物。
式(1)中、Lはm+n価の炭素数6〜30の芳香族炭化水素基又は4環以上の縮合複素環を含まない炭素数3〜30の芳香族複素環基、炭素数9〜30のトリアリールアミンから生じる基、又は炭素数6〜24のジアリールスルホンから生じる基を表す。XはN−A、O、S又はSeを表し、Aはそれぞれ独立して炭素数1〜30のアルキル基、炭素数3〜30のシクロアルキル基、炭素数2〜30のアルケニル基、炭素数2〜30のアルキニル基、炭素数3〜18のシリル基、炭素数2〜19のアシル基、炭素数6〜50の芳香族炭化水素基又は4環以上の縮合複素環を含まない炭素数3〜50の芳香族複素環基を表す。Rはそれぞれ独立して水素、炭素数1〜30のアルキル基、炭素数3〜30のシクロアルキル基、炭素数2〜30のアルケニル基、炭素数2〜30のアルキニル基、炭素数6〜30の芳香族炭化水素基又は4環以上の縮合複素環を含まない炭素数3〜30の芳香族複素環基を表す。mは1〜4の整数を表し、nは0〜3の整数を表す。mとnの総数は2〜4である。 - 一般式(1)において、nが0である請求項1に記載の含窒素芳香族化合物。
- 一般式(1)において、XがN−Aであることを特徴とする請求項1に記載の含窒素芳香族化合物。
- 一般式(1)において、mが2又は3であることを特徴とする請求項1に記載の化合物。
- 請求項1〜4のいずれかに記載の含窒素芳香族化合物を含むことを特徴とする有機半導体材料。
- 請求項5に記載の有機半導体材料で形成されることを特徴とする有機半導体薄膜。
- 請求項5に記載の有機半導体材料を使用したことを特徴とする有機電子デバイス。
- 有機電子デバイスが、発光素子、薄膜トランジスタ、又は光起電力素子のいずれかである請求項7に記載の有機電子デバイス。
- 発光素子が、有機電界発光素子である請求項8に記載の有機電子デバイス。
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