JP4085574B2 - Light emitting element - Google Patents
Light emitting element Download PDFInfo
- Publication number
- JP4085574B2 JP4085574B2 JP2000397144A JP2000397144A JP4085574B2 JP 4085574 B2 JP4085574 B2 JP 4085574B2 JP 2000397144 A JP2000397144 A JP 2000397144A JP 2000397144 A JP2000397144 A JP 2000397144A JP 4085574 B2 JP4085574 B2 JP 4085574B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- light emitting
- light
- emitting element
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 239000000463 material Substances 0.000 claims description 128
- 239000002019 doping agent Substances 0.000 claims description 49
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- 125000001424 substituent group Chemical group 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 230000005525 hole transport Effects 0.000 claims description 16
- 125000001931 aliphatic group Chemical group 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 239000011159 matrix material Substances 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
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- NKHUXLDXYURVLX-UHFFFAOYSA-N 2h-pyrrolo[3,4-c]pyrrole-4,6-dione Chemical class N1C=C2C(=O)NC(=O)C2=C1 NKHUXLDXYURVLX-UHFFFAOYSA-N 0.000 claims description 3
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- 125000003545 alkoxy group Chemical group 0.000 description 7
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- 230000015572 biosynthetic process Effects 0.000 description 3
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- 239000011651 chromium Substances 0.000 description 3
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- 238000002189 fluorescence spectrum Methods 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
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- 239000010931 gold Substances 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
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- 238000006862 quantum yield reaction Methods 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical class C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- YLYPIBBGWLKELC-RMKNXTFCSA-N 2-[2-[(e)-2-[4-(dimethylamino)phenyl]ethenyl]-6-methylpyran-4-ylidene]propanedinitrile Chemical compound C1=CC(N(C)C)=CC=C1\C=C\C1=CC(=C(C#N)C#N)C=C(C)O1 YLYPIBBGWLKELC-RMKNXTFCSA-N 0.000 description 2
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/004—Diketopyrrolopyrrole dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
Description
【０００１】
【発明の属する技術分野】
本発明は、電気エネルギーを光に変換できる素子であって、表示素子、フラットパネルディスプレイ、バックライト、照明、インテリア、標識、看板、電子写真機、光信号発生器などの分野に利用可能な発光素子に関する。
【０００２】
【従来の技術】
陰極から注入された電子と陽極から注入された正孔が両極に挟まれた有機蛍光体内で再結合する際に発光するという有機積層薄膜発光素子の研究が近年活発に行われている。この素子は、薄型、低駆動電圧下での高輝度発光、蛍光材料を選ぶことによる多色発光が特徴であり注目を集めている。
【０００３】
この研究は、コダック社のＣ．Ｗ．Ｔａｎｇらが有機積層薄膜素子が高輝度に発光することを示して以来（Ａｐｐｌ．Ｐｈｙｓ．Ｌｅｔｔ．５１（１２）２１，ｐ．９１３，１９８７）、多くの研究機関が検討を行っている。コダック社の研究グループが提示した有機積層薄膜発光素子の代表的な構成は、ＩＴＯガラス基板上に正孔輸送性のジアミン化合物、発光層であるトリス（８−キノリノラト）アルミニウム錯体、そして陰極としてＭｇ：Ａｇを順次設けたものであり、１０Ｖ程度の駆動電圧で１０００ｃｄ／ｍ２の緑色発光が可能であった。現在の有機積層薄膜発光素子は、上記の素子構成要素の他に電子輸送層を設けているものなど構成を変えているものもあるが、基本的にはコダック社の構成を踏襲している。
【０００４】
多色発光の中では緑色発光材料の研究が最も進んでおり、現在は赤色発光材料と青色発光材料において、耐久性に優れ十分な輝度と色純度特性を示すものが望まれ、特性向上を目指して鋭意研究がなされている。
【０００５】
赤色発光材料としては、ビス（ジイソプロピルフェニル）ペリレンなどのペリレン系、ペリノン系、ポルフィリン系、Ｅｕ錯体（Ｃｈｅｍ．Ｌｅｔｔ．，１２６７（１９９１））などが挙げられる。
【０００６】
また、赤色発光を得る手法として、ホスト材料の中に微量の赤色蛍光材料をドーパントとして混入させる方法も検討されている。ホスト材料としては、トリス（８−キノリノラト）アルミニウム錯体を始めとするキノリノール誘導体の金属錯体、ビス（１０−ベンゾキノリノラト）ベリリウム錯体、ジアリールブタジエン誘導体、スチルベン誘導体、ベンズオキサゾール誘導体、ベンゾチアゾール誘導体などがあげられ、その中にドーパントとして４−（ジシアノメチレン）−２−メチル−６−（ｐ−ジメチルアミノスチリル）−４Ｈ−ピラン、金属フタロシアニン（ＭｇＰｃ、ＡｌＰｃＣｌなど）化合物、スクアリリウム化合物、ビオラントロン化合物を存在させることによって赤色発光を取り出していた。
【０００７】
【発明が解決しようとする課題】
しかし、従来技術に用いられる発光材料（ホスト材料、ドーパント材料）には、発光効率が低く消費電力が高いものや、耐久性が低く素子寿命の短いものが多く、また、溶液状態では強い蛍光強度を有していても薄膜状態では濃度消光やエキサイプレックスあるいはエキサイマー形成により蛍光強度が著しく減少し、発光素子に適用した際に高輝度発光が得られないものが多かった。
【０００８】
特に赤色発光材料（ホスト材料およびドーパント材料）に関しては、色純度と輝度が両立したものが極めて少ないことが大きな問題であった。
【０００９】
本発明は、かかる問題を解決し、電気エネルギーの利用効率が高く、高輝度かつ高色純度の発光素子を提供することを目的とするものである。
【００１０】
【課題を解決するための手段】
本発明は陽極と陰極の間に発光物質が存在し、電気エネルギーにより発光する素子であって、該素子は発光ピーク波長が５８０ｎｍ以上７２０ｎｍ以下で発光し、少なくとも下記一般式（１）に示す化合物と下記一般式（６）で表されるピロメテン骨格を有する化合物を含むことを特徴とする発光素子である。
【００１１】
【化５】
（ここで、Ａは下記一般式（４）に示すジケトピロロ［３，４−ｃ］ピロール誘導体、Ｂは下記一般式（３）に示す骨格、ｎは２である。）
【００１３】
【化６】
（ここで、Ｒ１３およびＲ１４は同じでも異なっていてもよく、水素、アルキル基、シクロアルキル基、アラルキル基、アリール基、シリル基の中から選ばれる。βは前記Ｂとの連結部位を示す。）
【００１５】
【化７】
（ここで、Ｒ ６ 〜Ｒ １２ は同じでも異なっていてもよく、水素、アルキル基、シクロアルキル基、アラルキル基、アリール基、複素環基、ハロゲン、アミノ基、隣接置換基との間に形成される縮合環および脂肪族環の中から選ばれる。αは前記Ａとの連結部位を示す。）
【００１７】
【化８】
（ここで、Ｒ２２〜Ｒ２８のうち少なくとも一つは芳香環を含むかあるいは隣接置換基との間に縮合芳香環を形成し、残りは水素である。Ｒ２９およびＲ３０はフッ素であり、Ｘは炭素である。）
【００１９】
【発明の実施の形態】
本発明において陽極は、光を取り出すために透明であれば酸化錫、酸化インジウム、酸化錫インジウム（ＩＴＯ）などの導電性金属酸化物、あるいは金、銀、クロムなどの金属、ヨウ化銅、硫化銅などの無機導電性物質、ポリチオフェン、ポリピロール、ポリアニリンなどの導電性ポリマなど特に限定されるものでないが、ＩＴＯガラスやネサガラスを用いることが特に望ましい。透明電極の抵抗は素子の発光に十分な電流が供給できればよいので限定されないが、素子の消費電力の観点からは低抵抗であることが望ましい。例えば３００Ω／□以下のＩＴＯ基板であれば素子電極として機能するが、現在では１０Ω／□程度の基板の供給も可能になっていることから、低抵抗品を使用することが特に望ましい。ＩＴＯの厚みは抵抗値に合わせて任意に選ぶ事ができるが、通常１００〜３００ｎｍの間で用いられることが多い。また、ガラス基板はソーダライムガラス、無アルカリガラスなどが用いられ、また厚みも機械的強度を保つのに十分な厚みがあればよいので、０．５ｍｍ以上あれば十分である。ガラスの材質については、ガラスからの溶出イオンが少ない方がよいので無アルカリガラスの方が好ましいが、ＳｉＯ２などのバリアコートを施したソーダライムガラスも市販されているのでこれを使用できる。ＩＴＯ膜形成方法は、電子線ビーム法、スパッタリング法、化学反応法など特に制限を受けるものではない。
【００２０】
陰極は、電子を本有機物層に効率良く注入できる物質であれば特に限定されないが、一般に白金、金、銀、銅、鉄、錫、亜鉛、アルミニウム、インジウム、クロム、リチウム、ナトリウム、カリウム、カルシウム、マグネシウムなどがあげられるが、電子注入効率をあげて素子特性を向上させるためにはリチウム、ナトリウム、カリウム、カルシウム、マグネシウムまたはこれら低仕事関数金属を含む合金が有効である。しかし、これらの低仕事関数金属は、一般に大気中で不安定であることが多く、例えば、有機層に微量のリチウムやマグネシウム（真空蒸着の膜厚計表示で１ｎｍ以下）をドーピングして安定性の高い電極を使用する方法が好ましい例として挙げることができるが、フッ化リチウムのような無機塩の使用も可能であることから特にこれらに限定されるものではない。更に電極保護のために白金、金、銀、銅、鉄、錫、アルミニウム、インジウムなどの金属、またはこれら金属を用いた合金、そしてシリカ、チタニア、窒化ケイ素などの無機物、ポリビニルアルコール、塩化ビニル、炭化水素系高分子などを積層することが好ましい例として挙げられる。これらの電極の作製法も抵抗加熱、電子線ビーム、スパッタリング、イオンプレーティング、コーティングなど導通を取ることができれば特に制限されない。
【００２１】
本発明における発光物質とは、１）正孔輸送層／発光層、２）正孔輸送層／発光層／電子輸送層、３）発光層／電子輸送層、４）正孔輸送層／発光層／正孔阻止層、５）正孔輸送層／発光層／正孔阻止層／電子輸送層、６）発光層／正孔阻止層／電子輸送層そして、７）以上の組合わせ物質を一層に混合した形態のいずれであってもよい。即ち、素子構成としては、上記１）〜６）の多層積層構造の他に７）のように発光材料単独または発光材料と正孔輸送材料や電子輸送材料を含む層を一層設けるだけでもよい。さらに、本発明における発光物質は自ら発光するもの、その発光を助けるもののいずれにも該当し、発光に関与している化合物、層などを指すものである。
【００２２】
正孔輸送層は正孔輸送性物質単独または二種類以上の物質を積層、混合するか正孔輸送性物質と高分子結着剤の混合物により形成され、正孔輸送性物質としてはＮ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ジ（３−メチルフェニル）−４，４’−ジフェニル−１，１’−ジアミン、Ｎ，Ｎ’−ジナフチル−Ｎ，Ｎ’−ジフェニル−４，４’−ジフェニル−１，１’−ジアミンなどのトリフェニルアミン類、ビス（Ｎ−アリルカルバゾール）またはビス（Ｎ−アルキルカルバゾール）類、ピラゾリン誘導体、スチルベン系化合物、ヒドラゾン系化合物、オキサジアゾール誘導体やフタロシアニン誘導体、ポルフィリン誘導体に代表される複素環化合物、ポリマー系では前記単量体を側鎖に有するポリカーボネートやスチレン誘導体、ポリビニルカルバゾール、ポリシランなどが好ましいが、素子作製に必要な薄膜を形成し、陽極から正孔が注入できて、さらに正孔を輸送できる化合物であれば特に限定されるものではない。
【００２３】
発光層とは実際に発光物質が形成される層であり、本発明の発光素子は電気エネルギーによりピーク波長が５８０ｎｍ以上７２０ｎｍ以下で発光する。５８０ｎｍより小さいと、ピーク幅が狭くても色純度の良好な赤色発光を得ることが出来ず、７２０ｎｍより大きいと、視感度が悪くなるので、効率良い高輝度赤色発光を得ることができない。また、本発明の発光材料は下記一般式（１）に示す化合物と蛍光ピーク波長が５８０ｎｍ以上７２０ｎｍ以下の有機蛍光物質を含み、いずれもドーパント材料としてもホスト材料としても使用することができるが、下記一般式（１）に示す化合物をホスト材料とし、有機蛍光物質をドーパント材料として用いるドーピング法を好ましい方法として挙げることができる。
【００２４】
【化９】
ここで、Ａは有機蛍光性骨格、ＢはＡに対する等方回転がＡ−Ｂ間および／またはＢ−Ｂ間の立体反発により制限されている置換基、ｎは１〜４のいずれかの自然数である。
【００２６】
一般式（１）のＡは所望の発光色に応じて選択することができる。高輝度発光を得るためには、特に限定されるものではないが、例えばナフタレン、アントラセン、フェナンスレン、ピレン、トリフェニレン、ペリレン、トラキセン、フルオレン、インデン、９，９’−スピロビフルオレン、ジスチリルベンゼン誘導体、テトラフェニルブタジエン誘導体、スチルベン誘導体、などの芳香族炭化水素化合物や、フラン、ピロール、チオフェン、シロール、９−シラフルオレン、９，９’−スピロビシラフルオレン、トリアゾール、オキサジアゾール、ベンゾチオフェン、ベンゾフラン、インドール、ジベンゾチオフェン、ジベンゾフラン、カルバゾール、ベンズオキサゾール、ベンズイミダゾール、ベンズチアゾール、ベンズジオキサゾール、ベンズジイミダゾール、ベンズジチアゾール、フェナンスロイミダゾール、フェナンスロオキサゾール、イミダゾピリジン、フェナントロリン、ピラジン、ナフチリジン、キノキサリン、ピロロピリジン、ピリミジン、チオキサンテン、アルダジン、クマリン、フタルイミド、ナフタルイミド、ペリノン、ピリミドピリミジンなどの芳香族複素環化合物が、蛍光量子収率が高いため好適に用いることができる。さらに、キノリノールやベンズキノリノール、ベンズオキサゾール、ベンズイミダゾール、トリアゾール、アゾメチンなどを配位子とした各種の金属錯体も一般式（１）のＡとして用いてもかまわない。
【００２７】
一般式（１）のＢは、一般式（１）のＡの優れた蛍光特性を薄膜状態において保持し、発光素子において高輝度発光させる役割を担う置換基である。すなわちＢは、Ａに対する等方回転がＡ−Ｂ間またはＢ−Ｂ間の立体反発により制限されてしまう置換基を形成しているため、薄膜状態において励起エネルギーを置換基の回転により熱失活させてしまう確率を減少させ、蛍光量子収率が低下するのを防ぐ。また、ＢはＡに対してねじれるために発光材料分子どうしのスタッキングを防ぎ、濃度消光やエキサイプレックスあるいはエキサイマー形成を抑制することができる。これらの結果、発光素子において高輝度かつ高色純度の発光を得ることができる。この等方回転が制限されていることは、分子模型や分子計算で容易に確認することができる。
【００２８】
上記等方回転はＡ−Ｂ間またはＢ−Ｂ間いずれの立体反発によって制限されていても良いが、より高輝度な発光を得るためにはＡ−Ｂ間の立体反発により制限されている方が好ましい。このような効果を有するＢとして、下記一般式（２）に示す骨格を有している置換基が好適に用いられる。
【００２９】
【化１０】
ここで、Ｒ１〜Ｒ５は同じでも異なっていてもよく、水素、アルキル基、シクロアルキル基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、水酸基、メルカプト基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、複素環基、ハロゲン、ハロアルカン、ハロアルケン、ハロアルキン、シアノ基、アルデヒド基、カルボニル基、カルボキシル基、エステル基、カルバモイル基、アミノ基、ニトロ基、シリル基、シロキサニル基、隣接置換基との間に形成される縮合環および脂肪族環の中から選ばれる。但し、Ｒ１およびＲ５の少なくとも一つは水素以外の置換基であるか、隣接置換基との間に縮合環または脂肪族環を形成する。αは前記Ａとの連結部位を示す。
【００３１】
これらの置換基の内、アルキル基とは例えばメチル基、エチル基、プロピル基、ブチル基などの飽和脂肪族炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、シクロアルキル基とは例えばシクロプロピル、シクロヘキシル、ノルボルニル、アダマンチルなどの飽和脂環式炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、アラルキル基とは例えばベンジル基、フェニルエチル基などの脂肪族炭化水素を介した芳香族炭化水素基を示し、脂肪族炭化水素と芳香族炭化水素はいずれも無置換でも置換されていてもかまわない。また、アルケニル基とは例えばビニル基、アリル基、ブタジエニル基などの二重結合を含む不飽和脂肪族炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、シクロアルケニル基とは例えばシクロペンテニル基、シクロペンタジエニル基、シクロヘキセン基などの二重結合を含む不飽和脂環式炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、アルキニル基とは例えばアセチレニル基などの三重結合を含む不飽和脂肪族炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、アルコキシ基とは例えばメトキシ基などのエーテル結合を介した脂肪族炭化水素基を示し、脂肪族炭化水素基は無置換でも置換されていてもかまわない。また、アルキルチオ基とはアルコキシ基のエーテル結合の酸素原子が硫黄原子に置換されたものである。また、アリールエーテル基とは例えばフェノキシ基などのエーテル結合を介した芳香族炭化水素基を示し、芳香族炭化水素基は無置換でも置換されていてもかまわない。また、アリールチオエーテル基とはアリールエーテル基のエーテル結合の酸素原子が硫黄原子に置換されたものである。また、アリール基とは例えばフェニル基、ナフチル基、ビフェニル基、フェナントリル基、ターフェニル基、ピレニル基などの芳香族炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、複素環基とは例えばフリル基、チエニル基、オキサゾリル基、ピリジル基、キノリル基、カルバゾリル基などの炭素以外の原子を有する環状構造基を示し、これは無置換でも置換されていてもかまわない。ハロゲンとはフッ素、塩素、臭素、ヨウ素を示す。ハロアルカン、ハロアルケン、ハロアルキンとは例えばトリフルオロメチル基などの、前述のアルキル基、アルケニル基、アルキニル基の一部あるいは全部が、前述のハロゲンで置換されたものを示し、残りの部分は無置換でも置換されていてもかまわない。アルデヒド基、カルボニル基、エステル基、カルバモイル基、アミノ基には脂肪族炭化水素、脂環式炭化水素、芳香族炭化水素、複素環などで置換されたものも含み、さらに脂肪族炭化水素、脂環式炭化水素、芳香族炭化水素、複素環は無置換でも置換されていてもかまわない。シリル基とは例えばトリメチルシリル基などのケイ素化合物基を示し、これは無置換でも置換されていてもかまわない。シロキサニル基とは例えばトリメチルシロキサニル基などのエーテル結合を介したケイ素化合物基を示し、これは無置換でも置換されていてもかまわない。隣接置換基との間に形成される縮合環または脂肪族環は無置換でも置換されていてもかまわない。
【００３２】
一般式（１）のＲ１およびＲ５の少なくとも一つは水素以外の置換基であるか、隣接置換基との間に縮合環または脂肪族環を形成するため、上記Ａとの間に立体反発が生じ、ＢのＡに対する等方回転が制限される。
【００３３】
さらに、安定して高輝度発光を得るためには、上記Ｒ１およびＲ５の少なくとも一つが隣接置換基との間に縮合環を形成した方が耐久性に優れるためより好ましい。したがって前記Ｂとして、下記一般式（３）に示す骨格を有している置換基がより好適に用いられる。
【００３４】
【化１１】
ここで、Ｒ６〜Ｒ１２は同じでも異なっていてもよく、水素、アルキル基、シクロアルキル基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、水酸基、メルカプト基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、複素環基、ハロゲン、ハロアルカン、ハロアルケン、ハロアルキン、シアノ基、アルデヒド基、カルボニル基、カルボキシル基、エステル基、カルバモイル基、アミノ基、ニトロ基、シリル基、シロキサニル基、隣接置換基との間に形成される縮合環および脂肪族環の中から選ばれる。αは前記Ａとの連結部位を示す。これらの置換基の説明は上述したものと同じである。
【００３６】
上記Ｂの好適な例として、特に限定されるものではないが、具体的には下記のような構造が挙げられる。
【００３７】
【化１２】
【化１３】
また、本発明では赤色発光を得るために蛍光ピーク波長が５８０ｎｍ以上７２０ｎｍ以下の有機蛍光物質が用いられるが、具体的には従来から知られている、テリレンなどの芳香族炭化水素の縮合環誘導体、ピリジノチアジアゾールやピラゾロピリジン、ジケトピロロピロールなどの縮合複素環誘導体、ビス（ジイソプロピルフェニル）ペリレンテトラカルボン酸イミドなどのナフタルイミド誘導体、ペリノン誘導体、アセチルアセトンやベンゾイルアセトンとフェナントロリンなどを配位子とするＥｕ錯体などの希土類錯体、４−（ジシアノメチレン）−２−メチル−６−（ｐ−ジメチルアミノスチリル）−４Ｈ−ピランやその類縁体、マグネシウムフタロシアニン、アルミニウムクロロフタロシアニンなどの金属フタロシアニン誘導体、亜鉛ポルフィリンなどの金属ポルフィリン誘導体、チオフェン誘導体、ピロール誘導体、ローダミン化合物、デアザフラビン誘導体、クマリン誘導体、オキサジン化合物、フェノキサジン誘導体、フェノキサゾン誘導体、キナクリドン誘導体、ベンゾチオキサンテンやその類縁体、ジシアノエテニルアレーン誘導体などを用いることが出来るが特にこれらに限定されるものではない。
【００４０】
さらに、高輝度かつ高色純度の赤色発光を得るために発光材料として前記一般式（１）のＡが下記一般式（４）に示すジケトピロロ［３，４−ｃ］ピロール骨格を挙げることができる。
【００４１】
【化１４】
ここで、Ｒ１３およびＲ１４は同じでも異なっていてもよく、水素、アルキル基、シクロアルキル基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、水酸基、メルカプト基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、複素環基、ハロゲン、ハロアルカン、ハロアルケン、ハロアルキン、シアノ基、アルデヒド基、カルボニル基、カルボキシル基、エステル基、カルバモイル基、アミノ基、ニトロ基、シリル基、シロキサニル基の中から選ばれる。βは前記Ｂとの連結部位を示す。これらの置換基の説明は上述したものと同じである。
【００４３】
上記化合物の好適な例として、特に限定されるものではないが、以下のような化合物が挙げられる。
【００４４】
【化１５】
【化１６】
【化１７】
優れた色純度特性を持つ赤色発光を得るために、前記有機蛍光物質として下記一般式（５）に示すピロメテン骨格を有する化合物もしくはその金属錯体を好適に用いることができる。
【００４８】
【化１８】
ここで、Ｒ１５〜Ｒ２１のうち少なくとも一つは芳香環を含むかあるいは隣接置換基との間に縮合環を形成し、残りは水素、アルキル基、シクロアルキル基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、水酸基、メルカプト基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、複素環基、ハロゲン、ハロアルカン、ハロアルケン、ハロアルキン、シアノ基、アルデヒド基、カルボニル基、カルボキシル基、エステル基、カルバモイル基、アミノ基、ニトロ基、シリル基、シロキサニル基、隣接置換基との間に形成される縮合環および脂肪族環の中から選ばれる。Ｘは炭素または窒素であるが、窒素の場合には上記Ｒ２１は存在しない。金属錯体の金属は、ホウ素、ベリリウム、マグネシウム、クロム、鉄、コバルト、ニッケル、銅、亜鉛、白金から選ばれる少なくとも一種である。これらの置換基の説明は上述したものと同じである。
【００５０】
さらに、高輝度特性を得るためには、蛍光量子収率が高いものがより好ましい。そこで、前記ピロメテン骨格を有する化合物の金属錯体として、下記一般式（６）で表される化合物をより好適に用いることができる。
【００５１】
【化１９】
ここで、Ｒ２２〜Ｒ２８のうち少なくとも一つは芳香環を含むかあるいは隣接置換基との間に縮合芳香環を形成し、残りは水素、アルキル基、シクロアルキル基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、水酸基、メルカプト基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、複素環基、ハロゲン、ハロアルカン、ハロアルケン、ハロアルキン、シアノ基、アルデヒド基、カルボニル基、カルボキシル基、エステル基、カルバモイル基、アミノ基、ニトロ基、シリル基、シロキサニル基、隣接置換基との間に形成される縮合環および脂肪族環の中から選ばれる。Ｒ２９およびＲ３０は同じでも異なっていてもよく、ハロゲン、水素、アルキル、アリール、複素環基から選ばれる。Ｘは炭素または窒素であるが、窒素の場合には上記Ｒ２８は存在しない。これらの置換基の説明は上述したものと同じである。
【００５３】
上記のピロメテン骨格を有する化合物の金属錯体の好適な例として、特に限定されるものではないが、具体的には下記のような構造が挙げられる。
【００５４】
【化２０】
【化２１】
【化２２】
ホスト材料からドーパント材料へのエネルギー移動には、ホスト材料の蛍光スペクトルとドーパント材料の吸収スペクトル（励起スペクトル）の重なりが必要である。また前記ピロメテン骨格を有する化合物もしくはその金属錯体のように色純度に優れたドーパント材料のストークスシフト（励起スペクトルのピークと蛍光スペクトルのピークの差）は数〜数十ｎｍと狭く、５８０ｎｍ以上７２０ｎｍ以下のドーパント材料からの高色純度赤色発光を得ようとすると、ドーパント材料の吸収スペクトル（励起スペクトル）は黄色、黄橙色、橙色、赤橙色、赤色領域（５４０ｎｍ以上７２０ｎｍ以下）になる。ホスト材料の蛍光スペクトルが、黄色よりも短波長側の黄緑色、緑色、青緑色、青色、青紫色、紫色領域にありスペクトルの重なりが小さいと、エネルギー移動が速やかに行われず、ドーパント材料からの発光が得られなかったり、得られたとしてもホスト材料からの発光が残り、白色化するなど、高色純度の赤色発光が得られない。
【００５８】
上記の理由により、５８０ｎｍ以上７２０ｎｍ以下でドーパント材料が高輝度、高色純度で発光するには、ホスト材料は蛍光ピーク波長が５４０ｎｍ以上７２０ｎｍ以下であることがより好ましい。目安としては、黄色、黄橙色、橙色、赤橙色、赤色などの蛍光を有するものが該当する。したがって、一般式（１）をホスト材料として用いる場合、一般式（１）の黄色、黄橙色、橙色、赤橙色、赤色の蛍光を有することが好ましい。この場合、一般式（１）のＡ自体が黄色〜赤色の蛍光を有していてもよいし、Ｂの置換基の効果により一般式（１）が黄色〜赤色の蛍光を有するようになっていてもよい。
【００５９】
ドーピング量は、通常多すぎると濃度消光現象が起きるため、通常ホスト材料に対して１０重量％以下で用いることが好ましく、更に好ましくは２％以下である。ドーパント材料はホスト材料の全体に含まれていても、部分的に含まれていても、いずれであってもよい。ドーピング方法としては、ホスト材料との共蒸着法によって形成することができるが、ホスト材料と予め混合してから同時に蒸着しても良い。また、前記ピロメテン骨格を有する化合物もしくはその金属錯体は、極めて微量でも発光することから、ホスト材料に分散されているのみならず、微量の前記ピロメテン骨格を有する化合物もしくはその金属錯体をホスト材料にサンドイッチ状に挟んで使用することも可能である。この場合、一層でも二層以上ホスト材料と積層しても良い。さらに、ホストおよびドーパント材料は２種類以上の化合物から構成されていても良い。
【００６０】
また、発光材料に添加するドーパント材料は、前記ピロメテン骨格を有する化合物もしくはその金属錯体一種のみに限る必要はなく、本発明の化合物を複数混合して用いたり、既知のドーパント材料の一種類以上を本発明の化合物と混合して用いてもよい。
【００６１】
本発明における電子輸送性材料としては、電界を与えられた電極間において負極からの電子を効率良く輸送することが必要で、電子注入効率が高く、注入された電子を効率良く輸送することが望ましい。そのためには電子親和力が大きく、しかも電子移動度が大きく、さらに安定性に優れ、トラップとなる不純物が製造時および使用時に発生しにくい物質であることが要求される。このような条件を満たす物質として、トリス（８−キノリノラト）アルミニウム錯体に代表されるキノリノール誘導体金属錯体、トロポロン金属錯体、フラボノール金属錯体、ペリレン誘導体、ペリノン誘導体、ナフタレン、クマリン誘導体、オキサジアゾール誘導体、アルダジン誘導体、ビススチリル誘導体、ピラジン誘導体、フェナントロリン誘導体、シロール誘導体、キノキサリン誘導体、ホウ素化合物などが挙げられるが特に限定されるものではない。これらの電子輸送材料は単独でも用いられるが、異なる電子輸送材料と積層または混合して使用しても構わない。
【００６２】
正孔阻止層とは、電界を与えられた電極間において陽極からの正孔が陰極からの電子と再結合することなく移動するのを防止するための層であり、各層を構成する材料の種類によっては、この層を挿入することにより正孔と電子の再結合確率が増加し、発光効率の向上が望める場合がある。具体的にはフェナントロリン誘導体やトリアゾール誘導体、キノリノール金属錯体などが挙げられるが、素子作製に必要な薄膜を形成し、陽極からの正孔の移動を効率よく阻止できる化合物であれば特に限定されるものではない。これらの正孔阻止材料は単独でも用いられるが、異なる電子輸送材料と積層または混合して使用しても構わない。
【００６３】
以上の正孔輸送層、発光層、電子輸送層、正孔阻止層に用いられる材料は単独で各層を形成することができるが、高分子結着剤としてポリ塩化ビニル、ポリカーボネート、ポリスチレン、ポリ（Ｎ−ビニルカルバゾール）、ポリメチルメタクリレート、ポリブチルメタクリレート、ポリエステル、ポリスルフォン、ポリフェニレンオキサイド、ポリブタジエン、炭化水素樹脂、ケトン樹脂、フェノキシ樹脂、ポリサルフォン、ポリアミド、エチルセルロース、酢酸ビニル、ＡＢＳ樹脂、ポリウレタン樹脂などの溶剤可溶性樹脂や、フェノール樹脂、キシレン樹脂、石油樹脂、ユリア樹脂、メラミン樹脂、不飽和ポリエステル樹脂、アルキド樹脂、エポキシ樹脂、シリコーン樹脂などの硬化性樹脂などに分散させて用いることも可能である。
【００６４】
発光物質の形成方法は、抵抗加熱蒸着、電子ビーム蒸着、スパッタリング、分子積層法、コーティング法など特に限定されるものではないが、通常は、抵抗加熱蒸着、電子ビーム蒸着が特性面で好ましい。層の厚みは、発光物質の抵抗値にもよるので限定することはできないが、１〜１０００ｎｍの間から選ばれる。
【００６５】
綺麗な赤色表示を行わせるためには、発光スペクトルのピーク波長が５８０ｎｍ以上７２０ｎｍ以下、より好ましくは６００ｎｍ以上７００ｎｍ以下の範囲内であり、半値幅が１００ｎｍ以下であることが重要である。発光スペクトルは、できるだけ単一ピークであることが好ましいが、場合によっては他のピークとの重なりによって複数の極大点を有したり、ピークの裾に肩が現れることもある。本発明において、ピーク波長とは発光中心波長に値する主ピークの波長であり、半値幅とはこれらピーク全体において発光中心波長の高さの半分のところのピーク幅であると定義している。
【００６６】
電気エネルギーとは主に直流電流を指すが、パルス電流や交流電流を用いることも可能である。電流値および電圧値は特に制限はないが、素子の消費電力、寿命を考慮するとできるだけ低いエネルギーで最大の輝度が得られるようにするべきである。
【００６７】
本発明におけるマトリクスとは、表示のための画素が格子状に配置されたものをいい、画素の集合で文字や画像を表示する。画素の形状、サイズは用途によって決まる。例えばパソコン、モニター、テレビの画像および文字表示には、通常一辺が３００μｍ以下の四角形の画素が用いられるし、表示パネルのような大型ディスプレイの場合は、一辺がｍｍオーダーの画素を用いることになる。モノクロ表示の場合は、同じ色の画素を配列すればよいが、カラー表示の場合には、赤、赤、緑、青の画素を並べて表示させる。この場合、典型的にはデルタタイプとストライプタイプがある。そして、このマトリクスの駆動方法としては、線順次駆動方法やアクティブマトリックスのどちらでもよい。線順次駆動の方が構造が簡単であるという利点があるが、動作特性を考慮した場合、アクティブマトリックスの方が優れる場合があるので、これも用途によって使い分けることが必要である。
【００６８】
本発明におけるセグメントタイプとは、予め決められた情報を表示するようにパターンを形成し、決められた領域を発光させることになる。例えば、デジタル時計や温度計における時刻や温度表示、オーディオ機器や電磁調理器などの動作状態表示、自動車のパネル表示などがあげられる。そして、前記マトリクス表示とセグメント表示は同じパネルの中に共存していてもよい。
【００６９】
また本発明の発光素子はバックライトとしても好適に用いることができる。バックライトとは、主に自発光しない表示装置の視認性を向上させる目的に使用され、液晶表示装置、時計、オーディオ機器、自動車パネル、表示板、標識などに使用される。特に液晶表示装置、中でも薄型化が課題となっているパソコン用途のバックライトとしては、従来方式のものが蛍光灯や導光板からなっているため薄型化が困難であることを考えると本発明におけるバックライトは、薄型、軽量が特徴になる。
【００７０】
【実施例】
以下、実施例および比較例をあげて本発明を説明するが、本発明はこれらの例によって限定されるものではない。
【００７１】
実施例１
ＩＴＯ透明導電膜を１５０ｎｍ堆積させたガラス基板（旭硝子社製、１５Ω／□、電子ビーム蒸着品）を３０×４０ｍｍに切断、エッチングを行った。得られた基板をアセトン、セミコクリン５６で各々１５分間超音波洗浄してから、超純水で洗浄した。続いてイソプロピルアルコールで１５分間超音波洗浄してから熱メタノールに１５分間浸漬させて乾燥させた。この基板を素子を作製する直前に１時間ＵＶ−オゾン処理し、真空蒸着装置内に設置して、装置内の真空度が１×１０−５Ｐａ以下になるまで排気した。抵抗加熱法によって、まず正孔輸送材料としてＮ，Ｎ’−ジフェニル−Ｎ，Ｎ’−（３−メチルフェニル）−１，１’−ジフェニル−４，４’−ジアミン（ＴＰＤ）を５０ｎｍの厚さに蒸着し、正孔輸送層を形成した。次にホスト材料として下記に示すＨ２を、ドーパント材料として９−ジメチルアミノ−５Ｈ−ベンゾ（ａ）フェノキサジン−５−オン（ジクロロメタン溶液中の蛍光ピーク波長は６１２ｎｍ）を用いて、ドーパント材料の濃度が１ｗｔ％になるように２５ｎｍの厚さに共蒸着して発光層を形成し、２，９−ジメチル−４，７−ジフェニル−１，１０−フェナントロリンを２５ｎｍの厚さに蒸着して電子輸送層を形成した。次にリチウムを０．５ｎｍドーピングした後、銀を１５０ｎｍ蒸着して陰極を形成し、５×５ｍｍ角の素子を作製した。この発光素子からは、６００ｎｍに発光ピーク波長を有する発光が得られた。
【００７２】
【化２３】
実施例２
ドーパント材料として下記に示すＤ２（ジクロロメタン溶液中の蛍光ピーク波長は６２９ｎｍ）を用い、ドーパント濃度を０．３ｗｔ％とした以外は実施例１と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長が６３６ｎｍ、最高輝度が３４４０ｃｄ／ｍ２の高輝度かつ高色純度の赤色発光が得られた。
【００７４】
【化２４】
実施例３
ホスト材料として下記に示すＨ３を用い、ドーパント濃度を０．８５ｗｔ％とした以外は実施例２と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長が６３８ｎｍ、最高輝度が３１３０ｃｄ／ｍ２の高輝度かつ高色純度の赤色発光が得られた。
【００７６】
【化２５】
実施例４
ホスト材料として下記に示すＨ４を用い、ドーパント材料の濃度を０．１４ｗｔ％とした以外は実施例２と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長が６３４ｎｍ、最高輝度が３４７０ｃｄ／ｍ２の高輝度かつ高色純度の赤色発光が得られた。
【００７８】
【化２６】
実施例５
ホスト材料として下記に示すＨ５を、ドーパント材料として前記Ｄ２を用いて、ドーパント材料の濃度が０．３ｗｔ％になるように１５ｎｍの厚さに共蒸着し、次にホスト材料を３５ｎｍの厚さに蒸着して発光層を形成した以外は実施例３と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長が６３８ｎｍ、最高輝度が３４８０ｃｄ／ｍ２の高輝度かつ高色純度の赤色発光が得られた。
【００８０】
【化２７】
実施例６
正孔輸送材料として下記に示すＨＴＭ１を、ホスト材料として下記に示すＨ６を用い、ドーパント材料の濃度を０．３７ｗｔ％、発光層と電子輸送層の厚さをそれぞれ１５ｎｍと３５ｎｍとした以外は実施例２と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長が６３５ｎｍ、最高輝度が４６１０ｃｄ／ｍ２の高輝度かつ高色純度の赤色発光が得られた。
【００８２】
【化２８】
実施例７
ホスト材料として前記Ｈ２を、ドーパント材料として下記に示すＤ３（ジクロロメタン溶液中の蛍光ピーク波長は６０５ｎｍ）を用い、ドーパント材料の濃度を０．５５ｗｔ％、発光層と電子輸送層の厚さをそれぞれ１５ｎｍと４０ｎｍとした以外は実施例６と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長が６１２ｎｍ、最高輝度が７０４０ｃｄ／ｍ２の高輝度かつ高色純度の赤色発光が得られた。
【００８４】
【化２９】
実施例８
ドーパント材料として下記に示すＤ４（ジクロロメタン溶液中の蛍光ピーク波長は６２３ｎｍ）を用いた以外は実施例７と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長が６２８ｎｍ、最高輝度が４８９０ｃｄ／ｍ２の高輝度かつ高色純度の赤色発光が得られた。
【００８６】
【化３０】
実施例９
ドーパント材料として下記に示すＤ５（ジクロロメタン溶液中の蛍光ピーク波長は６０６ｎｍ）を用い、ドーパント材料の濃度を０．５ｗｔ％とした以外は実施例１と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長が６１３ｎｍ、最高輝度が７４８０ｃｄ／ｍ２の高輝度かつ高色純度の赤色発光が得られた。
【００８８】
【化３１】
実施例１０
ホスト材料として前記Ｈ３を用い、ドーパント材料の濃度を０．３ｗｔ％とした以外は実施例９と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長が６１３ｎｍ、最高輝度が５２８０ｃｄ／ｍ２の高輝度かつ高色純度の赤色発光が得られた。
【００９０】
実施例１１
正孔輸送材料として前記ＨＴＭ１を、ホスト材料として前記Ｈ２を、ドーパント材料として前記Ｄ５を用い、ドーパント材料の濃度を０．３４ｗｔ％とした以外は実施例５と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長が６１２ｎｍ、最高輝度が１１２４０ｃｄ／ｍ２の高輝度かつ高色純度の赤色発光が得られた。
【００９１】
実施例１２
ホスト材料として前記Ｈ４を用いた以外は実施例９と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長が６０６ｎｍ、最高輝度が４６００ｃｄ／ｍ２の高輝度かつ高色純度の赤色発光が得られた。
【００９２】
実施例１３
ホスト材料として前記Ｈ６を用い、ドーパント材料の濃度を０．６５ｗｔ％とした以外は実施例１２と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長が６１３ｎｍ、最高輝度が７０６０ｃｄ／ｍ２の高輝度かつ高色純度の赤色発光が得られた。
【００９３】
実施例１４
ホスト材料として前記Ｈ２を、ドーパント材料として下記に示すＤ６（ジクロロメタン溶液中の蛍光ピーク波長は６２１ｎｍ）を用いて、ドーパント材料の濃度が０．３ｗｔ％になるように１５ｎｍの厚さに共蒸着し、ホスト材料を３０ｎｍ蒸着して発光層を形成し、電子輸送層の厚さを５ｎｍとし、銀の代わりにアルミニウムを用いた以外は実施例１と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長が６２４ｎｍ、最高輝度が２２２０ｃｄ／ｍ２の高輝度かつ高色純度の赤色発光が得られた。
【００９４】
【化３２】
実施例１５
ドーパント材料として下記に示すＤ７（ジクロロメタン溶液中の蛍光ピーク波長は６１５ｎｍ）を用い、ドーパント材料の濃度を０．２６ｗｔ％とした以外は実施例１４と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長が６２１ｎｍ、最高輝度が２７７０ｃｄ／ｍ２の高輝度かつ高色純度の赤色発光が得られた。
【００９６】
【化３３】
実施例１６
ドーパント材料として下記に示すＤ８（ジクロロメタン溶液中の蛍光ピーク波長は６２０ｎｍ）を用い、ドーパント材料の濃度を０．３４ｗｔ％とした以外は実施例１４と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長が６２７ｎｍ、最高輝度が３４７０ｃｄ／ｍ２の高輝度かつ高色純度の赤色発光が得られた。
【００９８】
【化３４】
実施例１７
ドーパント材料として下記に示すＤ９（ジクロロメタン溶液中の蛍光ピーク波長は６４０ｎｍ）を用い、ドーパント材料の濃度を０．４３ｗｔ％とした以外は実施例１４と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長が６４７ｎｍ、最高輝度が１５０２ｃｄ／ｍ２の高輝度かつ高色純度の赤色発光が得られた。
【０１００】
【化３５】
実施例１８
ホスト材料として下記に示すＨ７を用い、ドーパント材料として下記に示すＤ１０（ジクロロメタン溶液中の蛍光ピーク波長は６１７ｎｍ）を用い、ドーパント材料の濃度が０．５ｗｔ％になるように２５ｎｍの厚さに共蒸着して発光層を形成し、トリス（８−キノリノラト）アルミニウム錯体を２５ｎｍ蒸着して電子輸送層を形成し、銀の代わりにアルミニウムを用いた以外は実施例１と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長が６２９ｎｍ、最高輝度が３２３０ｃｄ／ｍ２の高輝度かつ高色純度の赤色発光が得られた。
【０１０２】
【化３６】
実施例１９
ドーパント材料として前記Ｄ６を用いた以外は実施例１８と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長が６２９ｎｍ、最高輝度が１５００ｃｄ／ｍ２の高輝度かつ高色純度の赤色発光が得られた。
【０１０４】
比較例
ホスト材料として下記に示すＨ８を用いた以外は実施例２と同様にして発光素子を作製した。この発光素子からは、発光ピーク波長が６３８ｎｍ、最高輝度が１５０ｃｄ／ｍ２の低輝度な赤色発光しか得られなかった。
【０１０５】
【化３７】
実施例２０
ＩＴＯ透明導電膜を１５０ｎｍ堆積させたガラス基板（旭硝子社製、１５Ω／□、電子ビーム蒸着品）を３０×４０ｍｍに切断、フォトリソグラフィ法によって３００μｍピッチ（残り幅２７０μｍ）×３２本のストライプ状にパターン加工した。ＩＴＯストライプの長辺方向片側は外部との電気的接続を容易にするために１．２７ｍｍピッチ（開口部幅８００μｍ）まで広げてある。得られた基板をアセトン、セミコクリン５６で各々１５分間超音波洗浄してから、超純水で洗浄した。続いてイソプロピルアルコールで１５分間超音波洗浄してから熱メタノールに１５分間浸漬させて乾燥させた。この基板を素子を作製する直前に１時間ＵＶ−オゾン処理し、真空蒸着装置内に設置して、装置内の真空度が５×１０−４Ｐａ以下になるまで排気した。抵抗加熱法によって、まずＮ，Ｎ’−ジフェニル−Ｎ，Ｎ’−（３−メチルフェニル）−１，１’−ジフェニル−４，４’−ジアミン（ＴＰＤ）を１００ｎｍ蒸着した。次にホスト材料として前記Ｈ２を、ドーパント材料として前記Ｄ５を用いて、ドーパントが１ｗｔ％になるように５０ｎｍの厚さに共蒸着し、ホスト材料を５０ｎｍの厚さに積層した。次に厚さ５０μｍのコバール板にウエットエッチングによって１６本の２５０μmの開口部（残り幅５０μｍ、３００μｍピッチに相当）を設けたマスクを、真空中でＩＴＯストライプに直交するようにマスク交換し、マスクとＩＴＯ基板が密着するように裏面から磁石で固定した。そしてマグネシウムを５０ｎｍ、アルミニウムを１５０ｎｍ蒸着して３２×１６ドットマトリクス素子を作製した。本素子をマトリクス駆動させたところ、クロストークなく文字表示できた。
【０１０７】
【発明の効果】
本発明は、電気エネルギーの利用効率が高く、高輝度かつ高色純度の発光素子を提供できるものである。[0001]
BACKGROUND OF THE INVENTION
The present invention is an element that can convert electrical energy into light, and can be used in the fields of display elements, flat panel displays, backlights, lighting, interiors, signs, signboards, electrophotographic machines, optical signal generators, and the like. It relates to an element.
[0002]
[Prior art]
In recent years, research on an organic laminated thin film light emitting device in which light is emitted when electrons injected from a cathode and holes injected from an anode are recombined in an organic phosphor sandwiched between both electrodes has been actively conducted. This element is attracting attention because it is thin, has high luminance emission under a low driving voltage, and multicolor emission by selecting a fluorescent material.
[0003]
This study was conducted by C.D. W. Since Tang et al. Have shown that organic laminated thin-film elements emit light with high brightness (Appl. Phys. Lett. 51 (12) 21, p. 913, 1987), many research institutions have studied. A typical structure of an organic laminated thin film light emitting device presented by a research group of Kodak Company is a hole transporting diamine compound on an ITO glass substrate, a tris (8-quinolinolato) aluminum complex as a light emitting layer, and Mg as a cathode. : Ag is sequentially provided, and is 1000 cd / m with a driving voltage of about 10V.2Green light emission was possible. Some organic multilayer thin film light emitting elements have different configurations such as those provided with an electron transport layer in addition to the above-described element constituent elements, but basically follow the configuration of Kodak Company.
[0004]
Research on green light emitting materials is the most advanced among multicolor light emitting materials. Currently, red light emitting materials and blue light emitting materials that have excellent durability and sufficient luminance and color purity characteristics are desired. Have been intensively studied.
[0005]
Examples of the red light emitting material include perylene-based materials such as bis (diisopropylphenyl) perylene, perinone-based materials, porphyrin-based materials, and Eu complexes (Chem. Lett., 1267 (1991)).
[0006]
In addition, as a technique for obtaining red light emission, a method of mixing a small amount of a red fluorescent material as a dopant in a host material has been studied. Host materials include metal complexes of quinolinol derivatives such as tris (8-quinolinolato) aluminum complexes, bis (10-benzoquinolinolato) beryllium complexes, diarylbutadiene derivatives, stilbene derivatives, benzoxazole derivatives, benzothiazole derivatives, etc. Among them, 4- (dicyanomethylene) -2-methyl-6- (p-dimethylaminostyryl) -4H-pyran, metal phthalocyanine (MgPc, AlPcCl, etc.) compounds, squarylium compounds, violanthrone compounds are used as dopants. The red light emission was taken out by making it exist.
[0007]
[Problems to be solved by the invention]
However, many of the light-emitting materials (host materials and dopant materials) used in the prior art have low luminous efficiency and high power consumption, low durability and short device lifetime, and strong fluorescence intensity in the solution state. Even in the thin film state, the fluorescence intensity is remarkably reduced due to concentration quenching, exciplex formation, or excimer formation, and when applied to a light emitting device, there are many cases in which high luminance emission cannot be obtained.
[0008]
In particular, regarding red light-emitting materials (host materials and dopant materials), it was a big problem that there were very few materials having both color purity and luminance.
[0009]
An object of the present invention is to solve such problems and to provide a light-emitting element having high luminance and high color purity with high use efficiency of electric energy.
[0010]
[Means for Solving the Problems]
The present invention is an element in which a luminescent substance is present between an anode and a cathode and emits light by electric energy. The element emits light at an emission peak wavelength of 580 nm or more and 720 nm or less, and at least a compound represented by the following general formula (1) And a compound having a pyromethene skeleton represented by the following general formula (6).
[0011]
[Chemical5]
(Here, A is a diketopyrrolo [3,4-c] pyrrole derivative represented by the following general formula (4), and B is the following general formula (3), And n is 2. )
[0013]
[Chemical6]
(Where R13And R14May be the same or different and are selected from hydrogen, an alkyl group, a cycloalkyl group, an aralkyl group, an aryl group, and a silyl group. β represents the site of connection with B. )
[0015]
[Chemical7]
(Where R 6 ~ R 12 May be the same or different, and may be a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an aryl group, a heterocyclic group, a halogen, an amino group, or a condensed ring or an aliphatic ring formed between adjacent substituents. Chosen from the inside. α represents a linking site with A. )
[0017]
[Chemical8]
(Where R22~ R28At least one of them contains an aromatic ring or forms a condensed aromatic ring with an adjacent substituent, and the rest is hydrogen. R29And R30Is fluorine and X is carbon. )
[0019]
DETAILED DESCRIPTION OF THE INVENTION
In the present invention, if the anode is transparent for extracting light, a conductive metal oxide such as tin oxide, indium oxide and indium tin oxide (ITO), or a metal such as gold, silver and chromium, copper iodide, sulfide Inorganic conductive materials such as copper and conductive polymers such as polythiophene, polypyrrole, and polyaniline are not particularly limited, but it is particularly desirable to use ITO glass or Nesa glass. The resistance of the transparent electrode is not limited as long as a current sufficient for light emission of the element can be supplied, but it is desirable that the resistance be low from the viewpoint of power consumption of the element. For example, an ITO substrate of 300 Ω / □ or less functions as an element electrode. However, since it is now possible to supply a substrate of about 10 Ω / □, it is particularly desirable to use a low resistance product. The thickness of ITO can be arbitrarily selected according to the resistance value, but is usually used in a range of 100 to 300 nm. Further, soda lime glass, non-alkali glass or the like is used for the glass substrate, and the thickness of the glass substrate only needs to be sufficient to maintain the mechanical strength, so 0.5 mm or more is sufficient. As for the glass material, it is better to use alkali-free glass because it is better to have less ions eluted from the glass.2Since soda lime glass with a barrier coating such as is commercially available, it can be used. The ITO film forming method is not particularly limited, such as an electron beam method, a sputtering method, or a chemical reaction method.
[0020]
The cathode is not particularly limited as long as it can efficiently inject electrons into the organic layer, but is generally platinum, gold, silver, copper, iron, tin, zinc, aluminum, indium, chromium, lithium, sodium, potassium, calcium. Magnesium and the like can be mentioned, but lithium, sodium, potassium, calcium, magnesium or alloys containing these low work function metals are effective for improving the device characteristics by increasing the electron injection efficiency. However, these low work function metals are generally unstable in the atmosphere. For example, the organic layer is doped with a small amount of lithium or magnesium (1 nm or less in the vacuum vapor deposition thickness gauge display) to be stable. Although a method using a high electrode can be cited as a preferred example, it is not particularly limited to these because an inorganic salt such as lithium fluoride can be used. Furthermore, for electrode protection, metals such as platinum, gold, silver, copper, iron, tin, aluminum, indium, or alloys using these metals, and inorganic substances such as silica, titania, silicon nitride, polyvinyl alcohol, vinyl chloride, Preferred examples include laminating hydrocarbon polymers. The method for producing these electrodes is not particularly limited as long as electrical conduction such as resistance heating, electron beam, sputtering, ion plating, and coating can be achieved.
[0021]
The light emitting material in the present invention is 1) hole transport layer / light emitting layer, 2) hole transport layer / light emitting layer / electron transport layer, 3) light emitting layer / electron transport layer, 4) hole transport layer / light emitting layer. / Hole blocking layer, 5) hole transport layer / light emitting layer / hole blocking layer / electron transport layer, 6) light emitting layer / hole blocking layer / electron transport layer, and 7) a combination of the above materials in one layer Any of the mixed form may be sufficient. That is, as the element structure, in addition to the multilayer laminated structure of 1) to 6) above, only a single layer including a light emitting material alone or a layer containing a light emitting material and a hole transport material or an electron transport material may be provided. Furthermore, the luminescent substance in the present invention corresponds to both a substance that emits light by itself and a substance that assists the light emission, and refers to a compound, a layer, or the like that is involved in light emission.
[0022]
The hole transport layer is formed by laminating and mixing a hole transport material alone or two or more kinds of materials, or a mixture of a hole transport material and a polymer binder. '-Diphenyl-N, N'-di (3-methylphenyl) -4,4'-diphenyl-1,1'-diamine, N, N'-dinaphthyl-N, N'-diphenyl-4,4'- Triphenylamines such as diphenyl-1,1′-diamine, bis (N-allylcarbazole) or bis (N-alkylcarbazole) s, pyrazoline derivatives, stilbene compounds, hydrazone compounds, oxadiazole derivatives and phthalocyanine derivatives , Heterocyclic compounds typified by porphyrin derivatives, in the case of polymer systems, polycarbonates and styrene derivatives having the above monomers in the side chain, polyvinylcarbazo Le, is preferred such as polysilane, forming a thin film required for device fabrication, and can inject holes from the anode, and is not particularly limited as long as it is a further compound capable of transporting holes.
[0023]
A light-emitting layer is a layer in which a light-emitting substance is actually formed. The light-emitting element of the present invention emits light with a peak wavelength of 580 nm or more and 720 nm or less by electric energy. If it is smaller than 580 nm, red light emission with good color purity cannot be obtained even if the peak width is narrow, and if it is larger than 720 nm, visibility is deteriorated, so that efficient high luminance red light emission cannot be obtained. In addition, the light emitting material of the present invention includes a compound represented by the following general formula (1) and an organic fluorescent material having a fluorescence peak wavelength of 580 nm to 720 nm, both of which can be used as a dopant material and a host material. A preferable method is a doping method in which a compound represented by the following general formula (1) is used as a host material and an organic fluorescent material is used as a dopant material.
[0024]
[Chemical9]
Here, A is an organic fluorescent skeleton, B is a substituent whose isotropic rotation with respect to A is restricted by steric repulsion between AB and / or BB, and n is a natural number of 1 to 4 It is.
[0026]
A in the general formula (1) can be selected according to a desired emission color. In order to obtain high-intensity light emission, although not particularly limited, for example, naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, traxene, fluorene, indene, 9,9'-spirobifluorene, distyrylbenzene derivatives Aromatic hydrocarbon compounds such as tetraphenylbutadiene derivatives and stilbene derivatives, furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9′-spirobisilafluorene, triazole, oxadiazole, benzothiophene, Benzofuran, indole, dibenzothiophene, dibenzofuran, carbazole, benzoxazole, benzimidazole, benzthiazole, benzdioxazole, benzdiimidazole, benzdithiazole, phenanthroimi Aromatic heterocyclic compounds such as sol, phenanthroxazole, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, pyrimidine, thioxanthene, aldazine, coumarin, phthalimide, naphthalimide, perinone, pyrimidopyrimidine are fluorescent. Since the quantum yield is high, it can be suitably used. Furthermore, various metal complexes having quinolinol, benzquinolinol, benzoxazole, benzimidazole, triazole, azomethine, or the like as a ligand may be used as A in the general formula (1).
[0027]
B in the general formula (1) is a substituent that retains the excellent fluorescence characteristics of A in the general formula (1) in a thin film state and plays a role of causing high-intensity light emission in the light emitting element. That is, since B forms a substituent in which isotropic rotation with respect to A is restricted by steric repulsion between AB or BB, the excitation energy is thermally deactivated by rotation of the substituent in a thin film state. This reduces the probability that the fluorescence quantum yield is reduced. Further, since B is twisted with respect to A, stacking of light emitting material molecules can be prevented, and concentration quenching, exciplex or excimer formation can be suppressed. As a result, light emission with high luminance and high color purity can be obtained in the light-emitting element. The restriction of this isotropic rotation can be easily confirmed by a molecular model or molecular calculation.
[0028]
The isotropic rotation may be limited by the solid repulsion between A and B or B and B, but in order to obtain higher luminance light emission, it is limited by the solid repulsion between A and B. Is preferred. As B having such an effect, a substituent having a skeleton represented by the following general formula (2) is preferably used.
[0029]
[Chemical10]
Where R1~ R5May be the same or different, hydrogen, alkyl group, cycloalkyl group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, mercapto group, alkoxy group, alkylthio group, aryl ether group, aryl thioether group, Aryl group, heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group, siloxanyl group, adjacent substituent It is selected from fused rings and aliphatic rings formed between them. However, R1And R5At least one of these is a substituent other than hydrogen, or forms a condensed ring or an aliphatic ring with an adjacent substituent. α represents a linking site with A.
[0031]
Among these substituents, the alkyl group represents, for example, a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, or a butyl group, which may be unsubstituted or substituted. The cycloalkyl group represents a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, and the like, which may be unsubstituted or substituted. The aralkyl group is an aromatic hydrocarbon group via an aliphatic hydrocarbon such as a benzyl group or a phenylethyl group, and both the aliphatic hydrocarbon and the aromatic hydrocarbon may be unsubstituted or substituted. It doesn't matter. The alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond such as a vinyl group, an allyl group or a butadienyl group, which may be unsubstituted or substituted. The cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexene group, which may be unsubstituted or substituted. . The alkynyl group refers to an unsaturated aliphatic hydrocarbon group containing a triple bond such as an acetylenyl group, which may be unsubstituted or substituted. The alkoxy group refers to an aliphatic hydrocarbon group via an ether bond such as a methoxy group, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The alkylthio group is a group in which an oxygen atom of an ether bond of an alkoxy group is substituted with a sulfur atom. The aryl ether group refers to an aromatic hydrocarbon group via an ether bond such as a phenoxy group, and the aromatic hydrocarbon group may be unsubstituted or substituted. The arylthioether group is a group in which the oxygen atom of the ether bond of the arylether group is substituted with a sulfur atom. The aryl group represents an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, or a pyrenyl group, which may be unsubstituted or substituted. The heterocyclic group is a cyclic structural group having an atom other than carbon, such as a furyl group, a thienyl group, an oxazolyl group, a pyridyl group, a quinolyl group, or a carbazolyl group, which may be unsubstituted or substituted. Absent. Halogen is fluorine, chlorine, bromine or iodine. Haloalkane, haloalkene, haloalkyne means, for example, a part or all of the above-mentioned alkyl group, alkenyl group, alkynyl group such as trifluoromethyl group substituted with the above-mentioned halogen, and the remaining part may be unsubstituted It may be replaced. Aldehyde groups, carbonyl groups, ester groups, carbamoyl groups, amino groups include those substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocyclic rings, etc. The cyclic hydrocarbon, aromatic hydrocarbon and heterocyclic ring may be unsubstituted or substituted. A silyl group refers to a silicon compound group such as a trimethylsilyl group, which may be unsubstituted or substituted. The siloxanyl group refers to a silicon compound group via an ether bond such as a trimethylsiloxanyl group, which may be unsubstituted or substituted. The condensed ring or aliphatic ring formed between adjacent substituents may be unsubstituted or substituted.
[0032]
R in the general formula (1)1And R5At least one of them is a substituent other than hydrogen, or forms a condensed ring or an aliphatic ring with an adjacent substituent, so that a steric repulsion occurs with A, and B isotropically rotates with respect to A. Is limited.
[0033]
Further, in order to stably obtain high luminance light emission, the above R1And R5It is more preferable that a condensed ring is formed between at least one of the above and adjacent substituents because of excellent durability. Therefore, as B, a substituent having a skeleton represented by the following general formula (3) is more preferably used.
[0034]
[Chemical 1]1]
Where R6~ R12May be the same or different, hydrogen, alkyl group, cycloalkyl group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, mercapto group, alkoxy group, alkylthio group, aryl ether group, aryl thioether group, Aryl group, heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group, siloxanyl group, adjacent substituent It is selected from fused rings and aliphatic rings formed between them. α represents a linking site with A. The explanation of these substituents is the same as described above.
[0036]
A preferred example of B is not particularly limited, but specific examples thereof include the following structures.
[0037]
[Chemical 1]2]
[Chemical 1]3]
In the present invention, an organic fluorescent material having a fluorescence peak wavelength of 580 nm or more and 720 nm or less is used to obtain red light emission. Specifically, conventionally known condensed ring derivatives of aromatic hydrocarbons such as terylene are known. Ligands such as fused heterocyclic derivatives such as pyridinothiadiazole, pyrazolopyridine, diketopyrrolopyrrole, naphthalimide derivatives such as bis (diisopropylphenyl) perylenetetracarboxylic imide, perinone derivatives, acetylacetone, benzoylacetone and phenanthroline Rare earth complexes such as Eu complex, 4- (dicyanomethylene) -2-methyl-6- (p-dimethylaminostyryl) -4H-pyran and its analogs, metal phthalocyanine derivatives such as magnesium phthalocyanine, aluminum chlorophthalocyanine, Metalloporphyrin derivatives such as lead porphyrin, thiophene derivatives, pyrrole derivatives, rhodamine compounds, deazaflavin derivatives, coumarin derivatives, oxazine compounds, phenoxazine derivatives, phenoxazone derivatives, quinacridone derivatives, benzothioxanthene and its analogs, dicyanoethenylarene derivatives, etc. However, it is not particularly limited to these.
[0040]
Furthermore, in order to obtain red light emission having high luminance and high color purity, a diketopyrrolo [3,4-c] pyrrole skeleton in which A in the general formula (1) is represented by the following general formula (4) can be exemplified as a light emitting material. .
[0041]
[Chemical 1]4]
Where R13And R14May be the same or different, hydrogen, alkyl group, cycloalkyl group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, mercapto group, alkoxy group, alkylthio group, aryl ether group, aryl thioether group, The aryl group, heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group, and siloxanyl group are selected. β represents the site of connection with B. The explanation of these substituents is the same as described above.
[0043]
Although it does not specifically limit as a suitable example of the said compound, The following compounds are mentioned.
[0044]
[Chemical 1]5]
[Chemical 1]6]
[Chemical 1]7]
In order to obtain red light emission having excellent color purity characteristics, a compound having a pyromethene skeleton represented by the following general formula (5) or a metal complex thereof can be suitably used as the organic fluorescent substance.
[0048]
[Chemical 1]8]
Where R15~ R21At least one of them contains an aromatic ring or forms a condensed ring with an adjacent substituent, and the rest are hydrogen, alkyl group, cycloalkyl group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group , Mercapto group, alkoxy group, alkylthio group, aryl ether group, aryl thioether group, aryl group, heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group , An amino group, a nitro group, a silyl group, a siloxanyl group, a condensed ring formed between adjacent substituents and an aliphatic ring. X is carbon or nitrogen, but in the case of nitrogen, the above R21Does not exist. The metal of the metal complex is at least one selected from boron, beryllium, magnesium, chromium, iron, cobalt, nickel, copper, zinc, and platinum. The explanation of these substituents is the same as described above.
[0050]
Furthermore, in order to obtain a high luminance characteristic, a thing with a high fluorescence quantum yield is more preferable. Therefore, as the metal complex of the compound having the pyromethene skeleton, a compound represented by the following general formula (6) can be more suitably used.
[0051]
[Chemical19]
Where R22~ R28At least one of them contains an aromatic ring or forms a condensed aromatic ring with an adjacent substituent, and the rest are hydrogen, alkyl group, cycloalkyl group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, Hydroxyl group, mercapto group, alkoxy group, alkylthio group, aryl ether group, aryl thioether group, aryl group, heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl A group, an amino group, a nitro group, a silyl group, a siloxanyl group, a condensed ring formed between adjacent substituents and an aliphatic ring. R29And R30May be the same or different and are selected from halogen, hydrogen, alkyl, aryl, and heterocyclic groups. X is carbon or nitrogen, but in the case of nitrogen, the above R28Does not exist. The explanation of these substituents is the same as described above.
[0053]
Although it does not specifically limit as a suitable example of the metal complex of the compound which has said pyromethene frame | skeleton, Specifically, the following structures are mentioned.
[0054]
[Chemical20]
[Chemical 2]1]
[Chemical 2]2]
Energy transfer from the host material to the dopant material requires an overlap between the fluorescence spectrum of the host material and the absorption spectrum (excitation spectrum) of the dopant material. Further, the Stokes shift (difference between the peak of the excitation spectrum and the peak of the fluorescence spectrum) of the dopant material having excellent color purity such as the compound having the pyromethene skeleton or the metal complex thereof is as narrow as several to several tens nm, and is 580 nm to 720 nm. When an attempt is made to obtain high-purity red light emission from the dopant material, the absorption spectrum (excitation spectrum) of the dopant material becomes yellow, yellow-orange, orange, red-orange, and red regions (540 nm to 720 nm). If the fluorescence spectrum of the host material is in the yellow-green, green, blue-green, blue, blue-violet, or purple region on the shorter wavelength side than yellow and the spectrum overlap is small, energy transfer is not performed quickly, and Even if light emission cannot be obtained, or even if it is obtained, light emission from the host material remains and whitening occurs, so that red light emission with high color purity cannot be obtained.
[0058]
For the above reasons, in order for the dopant material to emit light with high brightness and high color purity at 580 nm or more and 720 nm or less, the host material preferably has a fluorescence peak wavelength of 540 nm or more and 720 nm or less. As a guideline, those having fluorescence such as yellow, yellow-orange, orange, red-orange, and red are applicable. Therefore, when using General formula (1) as a host material, it is preferable to have yellow, yellow-orange, orange, red-orange, and red fluorescence of General formula (1). In this case, A in the general formula (1) may have yellow to red fluorescence, or the general formula (1) has yellow to red fluorescence due to the effect of the substituent of B. May be.
[0059]
Since the concentration quenching phenomenon usually occurs when the doping amount is too large, the doping amount is preferably 10% by weight or less, more preferably 2% or less, based on the host material. The dopant material may be included in the host material as a whole, or may be included partially. As a doping method, it can be formed by a co-evaporation method with a host material, but it may be pre-mixed with the host material and then simultaneously deposited. In addition, since the compound having a pyromethene skeleton or a metal complex thereof emits light even in a very small amount, it is not only dispersed in the host material but also sandwiched between the compound having the pyromethene skeleton or the metal complex thereof in the host material. It is also possible to use it sandwiched between shapes. In this case, one or more layers may be laminated with the host material. Furthermore, the host and dopant material may be composed of two or more kinds of compounds.
[0060]
Further, the dopant material added to the light emitting material is not necessarily limited to the compound having the pyromethene skeleton or a single metal complex thereof, and a mixture of a plurality of the compounds of the present invention may be used, or one or more kinds of known dopant materials may be used. You may mix and use the compound of this invention.
[0061]
As the electron transporting material in the present invention, it is necessary to efficiently transport electrons from the negative electrode between electrodes to which an electric field is applied, and it is desirable that the electron injection efficiency is high and the injected electrons are transported efficiently. . For this purpose, it is required that the material has a high electron affinity, a high electron mobility, excellent stability, and a substance that does not easily generate trapping impurities during manufacturing and use. As substances satisfying such conditions, quinolinol derivative metal complexes represented by tris (8-quinolinolato) aluminum complexes, tropolone metal complexes, flavonol metal complexes, perylene derivatives, perinone derivatives, naphthalene, coumarin derivatives, oxadiazole derivatives, Examples thereof include, but are not limited to, aldazine derivatives, bisstyryl derivatives, pyrazine derivatives, phenanthroline derivatives, silole derivatives, quinoxaline derivatives, boron compounds and the like. These electron transport materials are used alone, but may be laminated or mixed with different electron transport materials.
[0062]
The hole blocking layer is a layer for preventing the holes from the anode from moving between the electrodes to which an electric field is applied without recombining with the electrons from the cathode, and the kind of material constituting each layer. Depending on the case, insertion of this layer may increase the probability of recombination of holes and electrons, and may improve the light emission efficiency. Specific examples include phenanthroline derivatives, triazole derivatives, quinolinol metal complexes, and the like, but any compound that can form a thin film necessary for device fabrication and efficiently block the movement of holes from the anode is particularly limited. is not. These hole blocking materials are used alone, but may be laminated or mixed with different electron transport materials.
[0063]
The materials used for the hole transport layer, the light emitting layer, the electron transport layer, and the hole blocking layer can form each layer alone, but as a polymer binder, polyvinyl chloride, polycarbonate, polystyrene, poly ( N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polysulfone, polyamide, ethyl cellulose, vinyl acetate, ABS resin, polyurethane resin, etc. It can also be used by being dispersed in a solvent-soluble resin, a curable resin such as a phenol resin, a xylene resin, a petroleum resin, a urea resin, a melamine resin, an unsaturated polyester resin, an alkyd resin, an epoxy resin, or a silicone resin.
[0064]
The method for forming the luminescent material is not particularly limited, such as resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, and coating method, but resistance heating vapor deposition and electron beam vapor deposition are usually preferred in terms of characteristics. The thickness of the layer depends on the resistance value of the luminescent material and cannot be limited, but is selected from 1 to 1000 nm.
[0065]
In order to achieve a beautiful red display, it is important that the peak wavelength of the emission spectrum is in the range of 580 nm to 720 nm, more preferably 600 nm to 700 nm, and the half width is 100 nm or less. The emission spectrum is preferably a single peak as much as possible, but in some cases, it may have a plurality of maximum points due to overlapping with other peaks, or a shoulder may appear at the bottom of the peak. In the present invention, the peak wavelength is the wavelength of the main peak worth the emission center wavelength, and the half width is defined as the peak width at half the height of the emission center wavelength in the entire peak.
[0066]
Electrical energy mainly refers to direct current, but pulsed current or alternating current can also be used. The current value and the voltage value are not particularly limited, but the maximum luminance should be obtained with the lowest possible energy in consideration of the power consumption and lifetime of the element.
[0067]
The matrix in the present invention refers to a matrix in which pixels for display are arranged in a lattice pattern, and displays characters and images by a set of pixels. The shape and size of the pixel are determined by the application. For example, a rectangular pixel with a side of 300 μm or less is normally used for displaying images and characters on a personal computer, monitor, television, etc. In a large display such as a display panel, a pixel with a side of mm order is used. . In monochrome display, pixels of the same color may be arranged. However, in color display, red, red, green, and blue pixels are displayed side by side. In this case, there are typically a delta type and a stripe type. The matrix driving method may be either a line sequential driving method or an active matrix. The line-sequential driving has an advantage that the structure is simple. However, the active matrix may be superior in consideration of the operation characteristics, so that it is necessary to properly use it depending on the application.
[0068]
The segment type in the present invention means that a pattern is formed so as to display predetermined information, and a predetermined region is caused to emit light. For example, the time and temperature display in a digital clock or a thermometer, the operation status display of an audio device or an electromagnetic cooker, the panel display of an automobile, etc. The matrix display and the segment display may coexist in the same panel.
[0069]
The light emitting device of the present invention can also be suitably used as a backlight. The backlight is used mainly for the purpose of improving the visibility of a display device that does not emit light, and is used for a liquid crystal display device, a clock, an audio device, an automobile panel, a display board, a sign, and the like. In particular, as a backlight for a liquid crystal display device, in particular, a personal computer application for which thinning is an issue, it is difficult to reduce the thickness of the conventional method because it is made of a fluorescent lamp or a light guide plate. The backlight is thin and lightweight.
[0070]
【Example】
EXAMPLES Hereinafter, although an Example and a comparative example are given and this invention is demonstrated, this invention is not limited by these examples.
[0071]
Example 1
A glass substrate (manufactured by Asahi Glass Co., Ltd., 15Ω / □, electron beam evaporated product) on which an ITO transparent conductive film was deposited to 150 nm was cut into 30 × 40 mm and etched. The obtained substrate was ultrasonically washed with acetone and semicocrine 56 for 15 minutes, respectively, and then washed with ultrapure water. Subsequently, it was ultrasonically cleaned with isopropyl alcohol for 15 minutes and then immersed in hot methanol for 15 minutes to dry. This substrate was subjected to UV-ozone treatment for 1 hour immediately before producing the device, and placed in a vacuum deposition apparatus, so that the degree of vacuum in the apparatus was 1 × 10.-5It exhausted until it became Pa or less. First, N, N′-diphenyl-N, N ′-(3-methylphenyl) -1,1′-diphenyl-4,4′-diamine (TPD) as a hole transport material is formed to a thickness of 50 nm by a resistance heating method. The hole transport layer was formed by vapor deposition. Next, H shown below as a host material2As dopant material9-Dimethylamino-5H-benzo (a) phenoxazin-5-one(The fluorescence peak wavelength in dichloromethane solution is612nm) to form a light-emitting layer by co-evaporation to a thickness of 25 nm so that the concentration of the dopant material is 1 wt%, and 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline is formed. An electron transport layer was formed by vapor deposition to a thickness of 25 nm. Next, after doping with 0.5 nm of lithium, 150 nm of silver was deposited to form a cathode, and a 5 × 5 mm square device was produced. From this light emitting element,600Light emission having an emission peak wavelength at nm was obtained..
[0072]
[23]
Example2
Example 2 except that D2 shown below (fluorescence peak wavelength in dichloromethane solution is 629 nm) was used as the dopant material, and the dopant concentration was 0.3 wt%1A light emitting element was manufactured in the same manner as described above. From this light emitting element, the emission peak wavelength is 636 nm, and the maximum luminance is 3440 cd / m.2The red light emission with high brightness and high color purity was obtained.
[0074]
[Chemical 2]4]
Example3
Example except that H3 shown below was used as a host material and the dopant concentration was 0.85 wt%2A light emitting element was manufactured in the same manner as described above. From this light emitting element, the emission peak wavelength is 638 nm, and the maximum luminance is 3130 cd / m.2The red light emission with high brightness and high color purity was obtained.
[0076]
[Chemical 2]5]
Example4
Example except that H4 shown below is used as the host material and the concentration of the dopant material is 0.14 wt%2A light emitting element was manufactured in the same manner as described above. From this light-emitting element, the emission peak wavelength is 634 nm and the maximum luminance is 3470 cd / m.2The red light emission with high brightness and high color purity was obtained.
[0078]
[Chemical 2]6]
Example5
H5 shown below as a host material and D2 as a dopant material are co-evaporated to a thickness of 15 nm so that the concentration of the dopant material is 0.3 wt%, and then the host material is made to a thickness of 35 nm. Example except that the light emitting layer was formed by vapor deposition3A light emitting element was manufactured in the same manner as described above. From this light-emitting element, the emission peak wavelength is 638 nm, and the maximum luminance is 3480 cd / m.2The red light emission with high brightness and high color purity was obtained.
[0080]
[Chemical27]
Example6
Implemented except that HTM1 shown below is used as the hole transport material, H6 shown below is used as the host material, the concentration of the dopant material is 0.37 wt%, and the thickness of the light emitting layer and the electron transport layer is 15 nm and 35 nm, respectively. Example2A light emitting element was manufactured in the same manner as described above. From this light emitting element, the emission peak wavelength was 635 nm, and the maximum luminance was 4610 cd / m.2The red light emission with high brightness and high color purity was obtained.
[0082]
[Chemical28]
Example7
Using H2 as a host material, D3 shown below as a dopant material (fluorescence peak wavelength in dichloromethane solution is 605 nm), the concentration of the dopant material is 0.55 wt%, and the thickness of the light emitting layer and the electron transport layer is 15 nm, respectively. Example except for 40nm6A light emitting element was manufactured in the same manner as described above. From this light emitting element, the emission peak wavelength is 612 nm, and the maximum luminance is 7040 cd / m.2The red light emission with high brightness and high color purity was obtained.
[0084]
[Chemical29]
Example8
Example except that D4 shown below (fluorescence peak wavelength in dichloromethane solution is 623 nm) was used as the dopant material7A light emitting element was manufactured in the same manner as described above. From this light emitting element, the emission peak wavelength is 628 nm, and the maximum luminance is 4890 cd / m.2The red light emission with high brightness and high color purity was obtained.
[0086]
[Chemical 3]0]
Example9
Example 5 except that D5 shown below (fluorescence peak wavelength in dichloromethane solution is 606 nm) is used as the dopant material and the concentration of the dopant material is 0.5 wt%1A light emitting element was manufactured in the same manner as described above. From this light-emitting element, the emission peak wavelength is 613 nm and the maximum luminance is 7480 cd / m.2The red light emission with high brightness and high color purity was obtained.
[0088]
[Chemical 3]1]
Example 10
Example except that H3 is used as a host material and the dopant material concentration is 0.3 wt%9A light emitting element was manufactured in the same manner as described above. From this light emitting element, the emission peak wavelength is 613 nm, and the maximum luminance is 5280 cd / m.2The red light emission with high brightness and high color purity was obtained.
[0090]
Example 11
Example except that the HTM1 is used as a hole transport material, the H2 is used as a host material, the D5 is used as a dopant material, and the concentration of the dopant material is 0.34 wt%.5A light emitting element was manufactured in the same manner as described above. From this light emitting element, the emission peak wavelength is 612 nm, and the maximum luminance is 11240 cd / m.2The red light emission with high brightness and high color purity was obtained.
[0091]
Example 12
Example except for using H4 as host material9A light emitting element was manufactured in the same manner as described above. From this light emitting element, the emission peak wavelength is 606 nm, and the maximum luminance is 4600 cd / m.2The red light emission with high brightness and high color purity was obtained.
[0092]
Example 13
Example 1 except that H6 was used as the host material and the dopant material concentration was 0.65 wt%.2A light emitting element was manufactured in the same manner as described above. From this light-emitting element, the emission peak wavelength is 613 nm and the maximum luminance is 7060 cd / m.2The red light emission with high brightness and high color purity was obtained.
[0093]
Example 14
Using H2 as a host material and D6 shown below as a dopant material (fluorescence peak wavelength in a dichloromethane solution is 621 nm), it is co-evaporated to a thickness of 15 nm so that the concentration of the dopant material is 0.3 wt%. A light-emitting element was fabricated in the same manner as in Example 1 except that a light-emitting layer was formed by vapor-depositing a host material at 30 nm, the thickness of the electron transport layer was 5 nm, and aluminum was used instead of silver. From this light-emitting element, the emission peak wavelength is 624 nm and the maximum luminance is 2220 cd / m.2The red light emission with high brightness and high color purity was obtained.
[0094]
[Chemical 3]2]
Example 15
Example 1 except that D7 shown below (fluorescence peak wavelength in dichloromethane solution is 615 nm) was used as the dopant material, and the concentration of the dopant material was 0.26 wt%.4A light emitting element was manufactured in the same manner as described above. From this light emitting element, the emission peak wavelength is 621 nm, and the maximum luminance is 2770 cd / m.2The red light emission with high brightness and high color purity was obtained.
[0096]
[Chemical 3]3]
Example 16
Example 1 except that D8 shown below (fluorescence peak wavelength in dichloromethane solution is 620 nm) was used as the dopant material, and the concentration of the dopant material was 0.34 wt%.4A light emitting element was manufactured in the same manner as described above. From this light emitting element, the emission peak wavelength is 627 nm, and the maximum luminance is 3470 cd / m.2The red light emission with high brightness and high color purity was obtained.
[0098]
[Chemical 3]4]
Example 17
Example 1 except that D9 shown below (fluorescence peak wavelength in dichloromethane solution is 640 nm) was used as the dopant material, and the concentration of the dopant material was 0.43 wt%.4A light emitting element was manufactured in the same manner as described above. From this light emitting element, the emission peak wavelength is 647 nm and the maximum luminance is 1502 cd / m.2The red light emission with high brightness and high color purity was obtained.
[0100]
[Chemical 3]5]
Example18
H7 shown below is used as the host material, D10 shown below as the dopant material (fluorescence peak wavelength in the dichloromethane solution is 617 nm), and the thickness of the dopant material is set to 25 nm so that the concentration of the dopant material is 0.5 wt%. A light-emitting layer is formed by vapor deposition, and a 25-nm tris (8-quinolinolato) aluminum complex is vapor-deposited to form an electron transport layer. A light-emitting element is fabricated in the same manner as in Example 1 except that aluminum is used instead of silver. did. From this light emitting element, the emission peak wavelength was 629 nm, and the maximum luminance was 3230 cd / m.2The red light emission with high brightness and high color purity was obtained.
[0102]
[Chemical 3]6]
Example19
Example except that D6 was used as dopant material18A light emitting element was manufactured in the same manner as described above. From this light emitting element, the emission peak wavelength is 629 nm, and the maximum luminance is 1500 cd / m.2The red light emission with high brightness and high color purity was obtained.
[0104]
Comparative example
Examples except that H8 shown below was used as a host material2A light emitting element was manufactured in the same manner as described above. From this light emitting device, the emission peak wavelength is 638 nm, and the maximum luminance is 150 cd / m.2Only low-intensity red light emission was obtained.
[0105]
[Chemical37]
Example 20
A glass substrate (manufactured by Asahi Glass Co., Ltd., 15Ω / □, electron beam evaporation product) on which an ITO transparent conductive film is deposited to 150 nm is cut into 30 × 40 mm, and 300 μm pitch (remaining width 270 μm) × 32 stripes by photolithography. Pattern processed. One side of the ITO stripe in the long side direction is expanded to a pitch of 1.27 mm (opening width 800 μm) in order to facilitate electrical connection with the outside. The obtained substrate was ultrasonically washed with acetone and semicocrine 56 for 15 minutes, respectively, and then washed with ultrapure water. Subsequently, it was ultrasonically cleaned with isopropyl alcohol for 15 minutes and then immersed in hot methanol for 15 minutes to dry. This substrate was treated with UV-ozone for 1 hour immediately before producing the device, and placed in a vacuum vapor deposition apparatus. The degree of vacuum in the apparatus was 5 × 10.-4It exhausted until it became Pa or less. First, N, N′-diphenyl-N, N ′-(3-methylphenyl) -1,1′-diphenyl-4,4′-diamine (TPD) was deposited by 100 nm by a resistance heating method. Next, H2 was used as the host material and D5 was used as the dopant material, so that the host material was co-evaporated to a thickness of 50 nm so that the dopant was 1 wt%, and the host material was laminated to a thickness of 50 nm. Next, a mask having 16 μm openings (corresponding to the remaining width of 50 μm and 300 μm pitch) formed by wet etching on a 50 μm thick Kovar plate was replaced by a mask so as to be orthogonal to the ITO stripe in a vacuum. And it fixed with the magnet from the back so that an ITO board | substrate might closely_contact | adhere. Magnesium was deposited with a thickness of 50 nm and aluminum was deposited with a thickness of 150 nm to produce a 32 × 16 dot matrix element. When this element was driven in matrix, characters could be displayed without crosstalk.
[0107]
【The invention's effect】
The present invention can provide a light-emitting element with high utilization efficiency of electric energy, high luminance, and high color purity.
Claims (6)
Priority Applications (1)
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| JP2000397144A JP4085574B2 (en) | 2000-01-06 | 2000-12-27 | Light emitting element |
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| JP2000-711 | 2000-01-06 | ||
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| JP2000397144A JP4085574B2 (en) | 2000-01-06 | 2000-12-27 | Light emitting element |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2001257078A (en) * | 2000-01-06 | 2001-09-21 | Toray Ind Inc | Luminous element |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| ATE541011T1 (en) | 2001-06-29 | 2012-01-15 | Basf Se | FLUORESCENT DIKETOPYRROLOPYRROLES |
| US20040151944A1 (en) * | 2001-12-03 | 2004-08-05 | Toshikazu Onikubo | Composition for organic electroluminescene element and organic electroluminescent using the same |
| JP3969300B2 (en) * | 2002-12-24 | 2007-09-05 | 東洋インキ製造株式会社 | Composition for organic electroluminescence device and organic electroluminescence device using the same |
| KR101130094B1 (en) * | 2003-04-10 | 2012-03-28 | 시바 홀딩 인크 | Fluorescent diketopyrrolopyrroles |
| AU2004242928B2 (en) | 2003-05-30 | 2011-03-10 | Gemin X Pharmaceuticals Canada Inc. | Triheterocyclic compounds, compositions, and methods for treating cancer or viral diseases |
| JP2008523023A (en) * | 2004-12-09 | 2008-07-03 | チバ ホールディング インコーポレーテッド | Fluorescent diketopyrrolopyrrole |
| EP1836165B1 (en) | 2004-12-28 | 2014-02-12 | Gemin X Pharmaceuticals Canada Inc. | Dipyrrole compounds, compositions, and methods for treating cancer or viral diseases |
| JP2008252063A (en) * | 2007-03-07 | 2008-10-16 | Toray Ind Inc | Light-emitting material and light-emitting element |
| US8278819B2 (en) | 2007-03-09 | 2012-10-02 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and display |
| KR102118142B1 (en) * | 2017-09-27 | 2020-06-02 | 삼성에스디아이 주식회사 | Compound for organic optoelectronic device, and organic optoelectronic device and display device |
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| JP2001257078A (en) * | 2000-01-06 | 2001-09-21 | Toray Ind Inc | Luminous element |
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