JPWO2018211377A1 - 電子デバイス、発光装置、電子機器、および照明装置 - Google Patents
電子デバイス、発光装置、電子機器、および照明装置 Download PDFInfo
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- JPWO2018211377A1 JPWO2018211377A1 JP2019518597A JP2019518597A JPWO2018211377A1 JP WO2018211377 A1 JPWO2018211377 A1 JP WO2018211377A1 JP 2019518597 A JP2019518597 A JP 2019518597A JP 2019518597 A JP2019518597 A JP 2019518597A JP WO2018211377 A1 JPWO2018211377 A1 JP WO2018211377A1
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Images
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- 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
-
- H—ELECTRICITY
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Abstract
Description
本実施の形態では、本発明の一態様の電子デバイスについて、図1を用いて以下説明する。
電子デバイス50は、一対の基板(基板10及び基板15)間に一対の電極(電極11及び電極12)と有機半導体層20を有する。有機半導体層20は少なくとも、キャリア輸送層30と機能層40を有する。なお、有機半導体層20は機能層を複数有していても良い。
以下では、本発明の一態様の電子デバイスの一例である発光素子について、図2を用いて以下説明する。
ここで、正孔注入層111に好適に用いることができる有機化合物について説明する。
また、本発明の一態様である電子デバイスにおいて、光路長を制御することで、さらに光取出し効率を向上させることができる。発光層130から得られる発光のうち、所望の波長の光を効率良く取り出すことができる。
次に、本発明の一態様に係る電子デバイスの一例であ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130は少なくとも、ホスト材料131を有し、さらにゲスト材料132を有すると好ましい。また、後述するように、ホスト材料131は有機化合物131_1及び有機化合物131_2を有していても良い。発光層130中では、ホスト材料131が重量比で最も多く存在し、ゲスト材料132は、ホスト材料131中に分散される。ゲスト材料132が蛍光性化合物の場合、発光層130のホスト材料131(有機化合物131_1及び有機化合物131_2)のS1準位は、発光層130のゲスト材料(ゲスト材料132)のS1準位よりも高いことが好ましい。また、ゲスト材料132が燐光性化合物の場合、発光層130のホスト材料131(有機化合物131_1及び有機化合物131_2)のT1準位は、発光層130のゲスト材料(ゲスト材料132)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、例えば電子受容性を有する遷移金属酸化物、フタロシアニン誘導体、芳香族アミン、ヘテロポリ酸などによって形成される。遷移金属酸化物としては、チタン酸化物、バナジウム酸化物、タンタル酸化物、モリブデン酸化物、タングステン酸化物、レニウム酸化物、ルテニウム酸化物、クロム酸化物、ジルコニウム酸化物、ハフニウム酸化物、銀酸化物などが挙げられ、該遷移金属酸化物は電子受容性に優れ、真空蒸着法や湿式法によって簡便に成膜を行うことができるため好ましい。また、フタロシアニン誘導体としては、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誘導体やフェニレンジアミン誘導体などが挙げられる。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。また、ヘテロポリ酸としては、リンモリブデン酸、リンタングステン酸、ケイモリブデン酸、ケイタングステン酸などが挙げられる。ヘテロポリ酸や高分子化合物は湿式法により簡便に成膜を行うことができるため好ましい。
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130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130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や金属錯体などを用いることができる。具体的には、発光層130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誘導体、ビピリジン誘導体、ピリミジン誘導体、トリアジン誘導体、キノキサリン誘導体、ジベンゾキノキサリン誘導体、フェナントロリン誘導体、トリアゾール誘導体、ベンゾイミダゾール誘導体、オキサジアゾール誘導体などが挙げられるが、窒素を二つ以上含む炭素数1乃至20の複素芳香族骨格を有すると好ましい。特に、ピリミジン骨格、及びトリアジン骨格を有する化合物であると好ましい。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118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は電極102からの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乃至数十nmサイズの半導体ナノ結晶であり、1×103個乃至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、およ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1に示す発光素子の構成と異なる構成の発光素子、及び当該発光素子の発光機構について、図3及び図4を用いて、以下説明を行う。なお、図3及び図4において、図2(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3(A)は、発光素子250の断面模式図である。
発光層120の発光機構について、以下説明を行う。
・Host(122):ホスト材料122
・SFG:ゲスト材料121(蛍光材料)のS1準位
・TFG:ゲスト材料121(蛍光材料)のT1準位
・SFH:ホスト材料122のS1準位
・TFH:ホスト材料122のT1準位
図4(A)は、発光素子252の断面模式図である。
次に、発光層140の発光機構について、以下説明を行う。
・Host(142_1):有機化合物142_1(ホスト材料)
・Host(142_2):有機化合物142_2(ホスト材料)
・TPG:ゲスト材料141(燐光材料)のT1準位
・SPH1:有機化合物142_1(ホスト材料)のS1準位
・TPH1:有機化合物142_1(ホスト材料)のT1準位
・SPH2:有機化合物142_2(ホスト材料)のS1準位
・TPH3:有機化合物142_2(ホスト材料)のT1準位
・SPE:励起錯体のS1準位
・TPE:励起錯体のT1準位
次に、発光層120、発光層140、及び発光層170に用いることのできる材料について、以下説明する。
発光層120中では、ホスト材料122が重量比で最も多く存在し、ゲスト材料121(蛍光材料)は、ホスト材料122中に分散される。ホスト材料122のS1準位は、ゲスト材料121(蛍光材料)のS1準位よりも高く、ホスト材料122のT1準位は、ゲスト材料121(蛍光材料)のT1準位よりも低いことが好ましい。
発光層140中では、ホスト材料142が重量比で最も多く存在し、ゲスト材料141(燐光材料)は、ホスト材料142中に分散される。発光層140のホスト材料142(有機化合物142_1及び有機化合物142_2)のT1準位は、ゲスト材料141のT1準位よりも高いことが好ましい。
発光層170に用いることのできる材料としては、実施の形態1に示す発光層に用いることのできる材料を援用すればよく、そうすることで、発光効率の高い発光素子を作製することができる。
図5(A)は、発光装置を示す上面図、図5(B)は図5(A)をA−Bおよび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6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7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照明装置に適用する一例について、図10及び図11を用いて説明する。本発明の一態様である発光素子を用いることで、発光効率が良好な、信頼性の高い照明装置を作製できる。
比較発光素子1乃至比較発光素子4、発光素子5乃至発光素子8及び発光素子9乃至発光素子12の正孔注入層111に用いた有機化合物と正孔注入層111の屈折率を測定した。屈折率はJ.A.Woolam社製回転補償子型多入射角高速分光エリプソメーター(M−2000U)を用いて室温で測定した。測定サンプルは石英基板上に真空蒸着法にて作製した。n Ordinary及びn Extraordinaryを測定し、n averageを算出した。
≪比較発光素子1乃至比較発光素子4の作製≫
ガラス基板上に電極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。なお、ITSO膜の波長が532nmの光における屈折率(n Ordinary)は2.07である。
発光素子5乃至発光素子8の作製工程は上記比較発光素子1乃至比較発光素子4の作製工程と正孔注入層111の作製工程のみ異なり、他の工程は比較発光素子1乃至比較発光素子4と同様に行った。
発光素子9乃至発光素子12の作製工程は上記比較発光素子1乃至比較発光素子4の作製工程と正孔注入層111の作製工程のみ異なり、他の工程は比較発光素子1乃至比較発光素子4と同様に行った。
次に、上記作製した比較発光素子1乃至比較発光素子4及び発光素子5乃至発光素子12の特性を測定した。輝度およびCIE色度の測定には色彩輝度計(トプコン社製、BM−5A)を用い、電界発光スペクトルの測定にはマルチチャンネル分光器(浜松ホトニクス社製、PMA−11)を用いた。なお、各発光素子の測定は室温(23℃に保たれた雰囲気)で行った。
図17に表4に示した各素子の値を用いて、各正孔注入層111に用いた有機材料による、色度xと外部量子効率の関係を示す。図17中、「DBT3P−II」の曲線のデータには比較発光素子1乃至比較発光素子4の値を、「dmCBP」の曲線のデータには発光素子5乃至発光素子8の値を、「TAPC」の曲線のデータには発光素子9乃至発光素子12の値を、それぞれ用いた。ここで、比較発光素子1乃至比較発光素子4及び発光素子5乃至発光素子12において、正孔注入層111の膜厚が同一の場合でも、用いている有機化合物によって、屈折率が異なるため、各発光素子の発光領域から基板までの光路長が変化する。光路長が変化すると、外部量子効率も変化するため、正孔注入層111の屈折率と外部量子効率の関係を評価するとき、各発光素子で光路長を調整する必要があるが、発光素子作製によるEL層膜厚の微調整は困難である。
ここで、正孔注入層111における電子供与性物質に対する電子受容性物質(MoO3)の体積比率(以下、MoO3の体積比率と示す)と外部量子効率の関係を調査した。また、素子構造の詳細を表5に示す。また、使用した化合物の構造と略称を以下に示す。なお、他の有機化合物については上述の化合物を参照すればよい。
発光素子13乃至発光素子18の作製工程は上記比較発光素子1乃至比較発光素子4の作製工程と正孔注入層111と発光層130の作製工程のみ異なり、他の工程は比較発光素子1乃至比較発光素子4と同様に行った。
次に、上記作製した発光素子13乃至発光素子18の輝度−外部量子効率特性を測定した。測定は上述の方法で行った。
比較発光素子19乃至比較発光素子22、発光素子23乃至発光素子26及び発光素子27乃至発光素子30の正孔注入層111に用いた有機化合物の屈折率を測定した。屈折率の測定は実施例1と同様に行った。
≪比較発光素子19乃至比較発光素子22の作製≫
比較発光素子19乃至比較発光素子22の作製工程は上記比較発光素子1乃至比較発光素子4の作製工程と正孔注入層111と発光層130の作製工程のみ異なり、他の工程は比較発光素子1乃至比較発光素子4と同様に行った。
発光素子23乃至発光素子26の作製工程は上記比較発光素子19乃至比較発光素子22の作製工程と正孔注入層111の作製工程のみ異なり、他の工程は比較発光素子19乃至比較発光素子22と同様に行った。
発光素子27乃至発光素子30の作製工程は上記比較発光素子19乃至比較発光素子22の作製工程と正孔注入層111の作製工程のみ異なり、他の工程は比較発光素子19乃至比較発光素子22と同様に行った。
次に、上記作製した比較発光素子19乃至比較発光素子22及び発光素子23乃至発光素子30の特性を測定した。測定は実施例1と同様に行った。
図24に表10に示した各素子の値を用いて、各正孔注入層111に用いた有機材料による、色度xと外部量子効率の関係を示す。図24中、「DBT3P−II」の曲線のデータには比較発光素子19乃至比較発光素子22の値を、「mCzFLP」の曲線のデータには発光素子23乃至発光素子26の値を、「FLP2A」の曲線のデータには発光素子27乃至発光素子30の値を、それぞれ用いた
比較発光素子31乃至比較発光素子34、発光素子35乃至発光素子38、発光素子39乃至発光素子42、発光素子43乃至発光素子46、比較発光素子47乃至比較発光素子50の正孔注入層111に用いた有機化合物及び比較発光素子31乃至比較発光素子34、発光素子35乃至発光素子38、発光素子39乃至発光素子42、発光素子43乃至発光素子46及び比較発光素子47乃至比較発光素子50に用いた正孔注入層111の屈折率を測定した。屈折率の測定は実施例1に記載の方法と同様に行った。
≪比較発光素子31乃至比較発光素子34の作製≫
ガラス基板上に電極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。
発光素子35乃至発光素子46及び比較発光素子47乃至比較発光素子50の作製工程は上記比較発光素子31乃至比較発光素子34の作製工程と正孔注入層111の作製工程のみ異なり、他の工程は比較発光素子31乃至比較発光素子34と同様に行った。素子構造の詳細は表11乃至表14に示す通りであるため、作製方法の詳細は省略する。
次に、上記作製した比較発光素子31乃至比較発光素子34、発光素子35乃至発光素子46及び比較発光素子47乃至比較発光素子50の特性を測定した。測定は実施例1と同様に行った。
次に、比較発光素子31、発光素子35、発光素子39、発光素子43及び比較発光素子47の2mAにおける定電流駆動試験を行った。その結果を図30に示す。図30から、比較発光素子31、発光素子35、発光素子39、発光素子43の信頼性は、比較発光素子47と比較し信頼性が良好であることが分かった。特に発光素子43の信頼性は良好であることが分かった。上述の通り、比較発光素子31、発光素子35、発光素子39、発光素子43の正孔注入層111に用いた有機化合物は分子内に電子供与性基を有しているため、比較発光素子47に用いたUGH−2と比較し、正孔注入性が良好であるためであると考えられる。よって、正孔注入層111の正孔注入性が良好な方が発光素子の信頼性が良好であることが分かった。なお、図30において、比較発光素子31、発光素子35及び発光素子39の信頼性試験結果は重なっている。
図31に表15に示した各素子の値を用いて、各正孔注入層111に用いた有機材料による、色度xと外部量子効率の関係を示す。図31中、「DBT3P−II」の曲線のデータには比較発光素子31乃至比較発光素子34の値を、「CzC」の曲線のデータには発光素子35乃至発光素子38の値を、「CzSi」の曲線のデータには発光素子39乃至発光素子42の値を、「FATPA」の曲線のデータには発光素子43乃至発光素子46の値を、「UGH−2」の曲線のデータには比較発光素子47乃至比較発光素子50の値をそれぞれ用いた。
比較発光素子51乃至比較発光素子54、比較発光素子55乃至比較発光素子58、発光素子59乃至発光素子62、発光素子63乃至発光素子66の正孔注入層111の屈折率を測定した。屈折率の測定は実施例1に記載の方法と同様に行った。波長が633nmの光における各膜の屈折率(n Ordinary)の値を表18に示す。
≪比較発光素子51乃至比較発光素子54の作製≫
ガラス基板上に電極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。
比較発光素子55乃至比較発光素子58及び発光素子59乃至発光素子66の作製工程は上記比較発光素子51乃至比較発光素子54の作製工程と正孔注入層111の作製工程のみ異なり、他の工程は比較発光素子51乃至比較発光素子54と同様に行った。素子構造の詳細は表16及び表17に示す通りであるため、作製方法の詳細は省略する。
次に、上記作製した比較発光素子51乃至比較発光素子58及び発光素子59乃至発光素子66の特性を測定した。測定は実施例1と同様に行った。1000cd/m2付近における各素子の特性を表19に示す。表19に示す外部量子効率は視野角補正を行う前の外部量子効率を示す。
図32に表19に示した各素子の値を用いて、各正孔注入層111に用いた有機材料による、色度yと外部量子効率の関係を示す。図32中、「β−TNB」の曲線のデータには比較発光素子51乃至比較発光素子54の値を、「NPB」の曲線のデータには比較発光素子55乃至比較発光素子58の値を、「BPAFLP」の曲線のデータには発光素子59乃至発光素子62の値を、「TAPC」の曲線のデータには発光素子63乃至発光素子66の値をそれぞれ用いた。
本参考例では、実施例1で用いた、Ir(pbi−diBuCNp)3の合成方法について説明する。
4−アミノ−3,5−ジクロロベンゾニトリル52g(280mmol)、イソブチルボロン酸125g(1226mmol)、リン酸三カリウム260g(1226mmol)、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)5.4g(13.1mmol)、トルエン1500mLを3000mL三口フラスコに入れ、フラスコ内を窒素置換し、フラスコ内を減圧しながら攪拌し、この混合物を脱気した。脱気後、トリス(ジベンジリデンアセトン)ジパラジウム(0)4.8g(5.2mmol)を加え、窒素気流下、130℃で12時間攪拌した。得られた反応溶液にトルエンを加えて、セライト(和光純薬工業株式会社、カタログ番号:531−16855)/フロリジール(和光純薬工業株式会社、カタログ番号:540−00135)/酸化アルミニウムの順に積層したろ過補助剤を通して吸引ろ過した。得られたろ液を濃縮し、油状物を得た。得られた油状物をシリカカラムクロマトグラフィーにより精製した。展開溶媒には、トルエンを用いた。得られたフラクションを濃縮して、黄色油状物を61g、収率95%で得た。核磁気共鳴法(NMR)により得られた黄色油状物が4−アミノ−3,5−ジイソブチルベンゾニトリルであることを確認した。ステップ1の合成スキームを下記式(a−1)に示す。
ステップ1で合成した4−アミノ−3,5−ジイソブチルベンゾニトリル30g(131mmol)、炭酸セシウム86g(263mmol)、ジメチルスルホキシド(DMSO)380mL、2−フルオロニトロベンゼン19g(131mmol)を1000mL三口フラスコに入れ、窒素気流下、120℃で20時間攪拌した。所定時間経過後の反応溶液を、クロロホルムによる抽出を行い粗生成物を得た。得られた粗生成物をシリカカラムクロマトグラフィーにより精製した。展開溶媒には、ヘキサン:酢酸エチル=7:1を用いた。得られたフラクションを濃縮して、橙色固体を得た。得られた固体にヘキサンを加えて吸引ろ過し、黄色固体を16g、収率35%で得た。核磁気共鳴法(NMR)により得られた黄色固体が4−[N−(2−ニトロフェニル)アミノ]−3,5−ジイソブチルベンゾニトリルであることを確認した。ステップ2の合成スキームを下記式(a−2)に示す。
ステップ2で合成した4−[N−(2−ニトロフェニル)アミノ]−3,5−ジイソブチルベンゾニトリル21g(60.0mmol)、水11mL(0.6mol)、エタノール780mLを2000mL三口フラスコに入れ、撹拌した。この混合物に塩化スズ(II)57g(0.3mol)を加え、窒素気流下、80℃で7.5時間撹拌した。所定時間経過後、この混合物を2M水酸化ナトリウム水溶液400mLに注ぎ、16時間室温で撹拌した。析出した沈殿物を吸引ろ過することで除去し、さらにクロロホルムで洗浄し、ろ液を得た。得られたろ液をクロロホルムによる抽出を行った。その後、抽出した溶液を濃縮して白色固体を20g、収率100%で得た。核磁気共鳴法(NMR)により得られた白色固体が4−[N−(2−アミノフェニル)アミノ]−3,5−ジイソブチルベンゾニトリルであることを確認した。ステップ3の合成スキームを下記式(a−3)に示す。
ステップ3で合成した4−[N−(2−アミノフェニル)アミノ]−3,5−ジイソブチルベンゾニトリル20g(60.0mmol)、アセトニトリル200mL、ベンズアルデヒド6.4g(60.0mmol)を1000mLナスフラスコに入れ、100℃で1時間攪拌した。この混合物に塩化鉄(III)100mg(0.60mmol)を加え、100℃で24時間攪拌した。所定時間経過後の反応溶液を、クロロホルムによる抽出を行い、油状物を得た。得られた油状物にトルエンを加えて、セライト/フロリジール/酸化アルミニウムの順に積層したろ過補助剤を通して吸引ろ過した。得られたろ液を濃縮し、油状物を得た。得られた油状物をシリカカラムクロマトグラフィーにより精製した。展開溶媒には、トルエンを用いた。得られたフラクションを濃縮して、固体を得た。この固体を酢酸エチル/ヘキサンで再結晶したところ、目的物である白色固体を4.3g、収率18%で得た。核磁気共鳴法(NMR)により得られた白色固体が1−(4−シアノ−2,6−ジイソブチルフェニル)−2−フェニル−1H−ベンゾイミダゾール(略称:Hpbi−diBuCNp)であることを確認した。ステップ4の合成スキームを下記式(a−4)に示す。
ステップ4で合成した1−(4−シアノ−2,6−ジイソブチルフェニル)−2−フェニル−1H−ベンゾイミダゾール(略称:Hpbi−diBuCNp)1.8g(4.4mmol)、トリス(アセチルアセトナト)イリジウム(III)0.43g(0.88mmol)を、三方コックを付けた反応容器に入れ、250℃にて39時間加熱した。得られた反応混合物にトルエンを加え、不溶物を取り除いた。得られたろ液を濃縮し、固体を得た。得られた固体をシリカカラムクロマトグラフィー(中性シリカ)により精製した。展開溶媒には、トルエンを用いた。得られたフラクションを濃縮して、固体を得た。得られた固体を酢酸エチル/ヘキサンで再結晶し、黄色固体を0.26g、収率21%で得た。合成スキームを下記式(a−5)に示す。
Claims (22)
- 第1の電極と、第2の電極と、第1の層と、第2の層と、を有し、
前記第1の層は、前記第1の電極と、前記第2の層と、の間に設けられ、
前記第2の層は、前記第1の層と、前記第2の電極と、の間に設けられ、
前記第1の層は、第1の物質と、第1の有機化合物と、を有し、
前記第1の物質は、電子受容性を有し、
前記第1の有機化合物を薄膜とした際の屈折率は、1以上1.75以下である、
電子デバイス。 - 第1の電極と第2の電極の間に、第1の層を有し、
前記第1の層は第1の有機化合物及び第1の物質を有し、
前記第1の有機化合物は第1の骨格と電子供与性骨格とを有し、
前記第1の骨格はテトラアリールメタン骨格またはテトラアリールシラン骨格である、電子デバイス。 - 第1の電極と、第2の電極との間に、第1の層と、第2の層と、第3の層と、を有し、
前記第1の層は、前記第1の電極と、前記第2の層と、の間に設けられ
前記第2の層は、前記第1の層と、前記第3の層と、の間に設けられ、
前記第1の層は、第1の物質と、第1の有機化合物と、を有し、
前記第1の物質は、電子受容性を有し、
前記第3の層は光を発するまたは吸収する機能を有し、
前記第1の層の屈折率は、前記第2の層の屈折率及び前記第3の屈折率の双方よりも低く、
前記第1の有機化合物を薄膜とした際の屈折率は、1以上1.75以下である、電子デバイス。 - 請求項2において、
前記第1の層の屈折率は1以上1.75以下である、電子デバイス。 - 請求項2において、
前記テトラアリールメタン骨格及び前記テトラアリールシラン骨格におけるアリール基はそれぞれ独立に、置換又は無置換の炭素数6乃至13のアリール基である、電子デバイス。
なお、前記アリール基どうしは互いに結合し、環を形成してもよい。 - 請求項5において、
前記アリール基はそれぞれ独立に、置換又は無置換のフェニル基である、電子デバイス。
なお、前記フェニル基どうしは互いに結合し、環を形成してもよい。 - 請求項2において、
前記電子供与性骨格は少なくとも、ピロール骨格、芳香族アミン骨格、アクリジン骨格、アゼピン骨格のうち、いずれか一を含む、電子デバイス。 - 請求項2において、
前記第1の有機化合物のガラス転移点(Tg)が100℃以上である、電子デバイス。 - 請求項1または請求項2において、
前記第1の層の屈折率は前記第2の層の屈折率よりも低い、電子デバイス。 - 請求項1または請求項3において、
前記第1の有機化合物は電子供与性を有する、電子デバイス。 - 請求項3において、
前記第3の層は、前記第2の層と接する、電子デバイス。 - 請求項1乃至請求項3のいずれか一項において、
前記第1の層は、前記第2の層と接する、電子デバイス。 - 請求項1乃至請求項3のいずれか一項において、
前記第1の層の屈折率は、前記第1の電極の屈折率よりも低い、電子デバイス。 - 請求項1乃至請求項3のいずれか一項において、
前記第1の有機化合物に対して、前記第1の物質の体積比率は、0.01以上0.3以下である、電子デバイス。 - 請求項1乃至請求項3のいずれか一項において、
前記第1の物質は、チタン酸化物、バナジウム酸化物、タンタル酸化物、モリブデン酸化物、タングステン酸化物、レニウム酸化物、ルテニウム酸化物、クロム酸化物、ジルコニウム酸化物、ハフニウム酸化物、及び銀酸化物のいずれか一を含む、電子デバイス。 - 請求項1乃至請求項3のいずれか一項において、
前記第1の物質は、TCNQ、F4TCNQ、及びF6TCNNQのいずれか一である、電子デバイス。 - 請求項1乃至請求項3のいずれか一項において、
前記第1の電極は陽極であり、前記第2の電極が陰極である、電子デバイス。 - 請求項1乃至請求項3のいずれか一項において、
前記第2の層は、発光機能を有する、電子デバイス。 - 請求項1乃至請求項3のいずれか一項において、
前記第2の層は、光電変換機能を有する、電子デバイス。 - 請求項1乃至請求項3のいずれか一項に記載の電子デバイスと、
カラーフィルタまたはトランジスタの少なくとも一方と、
を有する表示装置。 - 請求項20に記載の表示装置と、
筐体またはタッチセンサの少なくとも一方と、
を有する電子機器。 - 請求項1乃至請求項3のいずれか一項に記載の電子デバイスと、
筐体またはタッチセンサの少なくとも一方と、
を有する照明装置。
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WO2018211377A1 (ja) | 2018-11-22 |
JP2023082169A (ja) | 2023-06-13 |
JP2023082168A (ja) | 2023-06-13 |
KR20200007839A (ko) | 2020-01-22 |
US10950805B2 (en) | 2021-03-16 |
JP7257952B2 (ja) | 2023-04-14 |
DE112018008264B4 (de) | 2023-11-30 |
DE112018002586T5 (de) | 2020-03-05 |
US20200176692A1 (en) | 2020-06-04 |
DE112018002586B4 (de) | 2023-03-09 |
KR20220003140A (ko) | 2022-01-07 |
US20210257562A1 (en) | 2021-08-19 |
CN110603658A (zh) | 2019-12-20 |
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