JP3945032B2 - Luminescent material for organic electroluminescence device and organic electroluminescence device using the same - Google Patents
Luminescent material for organic electroluminescence device and organic electroluminescence device using the same Download PDFInfo
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- JP3945032B2 JP3945032B2 JP22550498A JP22550498A JP3945032B2 JP 3945032 B2 JP3945032 B2 JP 3945032B2 JP 22550498 A JP22550498 A JP 22550498A JP 22550498 A JP22550498 A JP 22550498A JP 3945032 B2 JP3945032 B2 JP 3945032B2
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- 125000005493 quinolyl group Chemical group 0.000 description 1
- LUDZVVVPVCUUBP-UHFFFAOYSA-N quinoxaline-2,3-diamine Chemical compound C1=CC=C2N=C(N)C(N)=NC2=C1 LUDZVVVPVCUUBP-UHFFFAOYSA-N 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- NVCBVYYESHBQKS-UHFFFAOYSA-L zinc;2-carboxyquinolin-8-olate Chemical compound [Zn+2].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1.C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 NVCBVYYESHBQKS-UHFFFAOYSA-L 0.000 description 1
Description
【０００１】
【産業上の利用分野】
本発明は平面光源や表示に使用される有機エレクトロルミネッセンス（ＥＬ）素子用発光材料および高輝度の発光素子に関するものである。
【０００２】
【従来の技術】
有機物質を使用したＥＬ素子は、固体発光型の安価な大面積フルカラー表示素子としての用途が有望視され、多くの開発が行われている。一般にＥＬ素子は、発光層および該層をはさんだ一対の対向電極から構成されている。発光は、両電極間に電界が印加されると、陰極側から電子が注入され、陽極側から正孔が注入される。さらに、この電子が発光層において正孔と再結合し、エネルギー準位が伝導帯から価電子帯に戻る際にエネルギーを光として放出する現象である。
【０００３】
従来の有機ＥＬ素子は、無機ＥＬ素子に比べて駆動電圧が高く、発光輝度や発光効率も低かった。また、特性劣化も著しく実用化には至っていなかった。
近年、１０Ｖ以下の低電圧で発光する高い蛍光量子効率を持った有機化合物を含有した薄膜を積層した有機ＥＬ素子が報告され、関心を集めている（アプライド・フィジクス・レターズ、５１巻、９１３ページ、１９８７年参照）。
この方法は、金属キレート錯体を発光層、アミン系化合物を正孔注入層に使用して、高輝度の緑色発光を得ており、６〜７Ｖの直流電圧で輝度は数１０００ｃｄ／ｍ2、最大発光効率は１．５ｌｍ／Ｗを達成して、実用領域に近い性能を持 っている。
【０００４】
しかしながら、現在までの有機ＥＬ素子は、構成の改善により発光強度は改良されているが、未だ充分な発光輝度は有していない。また、繰り返し使用時の安定性に劣るという大きな問題を持っている。これは、例えば、トリス（８−ヒドロキシキノリナート）アルミニウム錯体等の金属キレート錯体が、電界発光時に化学的に不安定であり、陰極との密着性も悪く、短時間の発光で大きく劣化していた。以上の理由により、高い発光輝度、発光効率を持ち、繰り返し使用時での安定性の優れた有機ＥＬ素子の開発のために、優れた発光能力を有し、耐久性のある発光材料の開発が望まれている。
【０００５】
【発明が解決しようとする課題】
本発明は、発光輝度が高く、繰り返し使用時での安定性の優れた有機ＥＬ素子の提供にある。本発明者らが鋭意検討した結果、一般式［１］で示される有機ＥＬ素子用発光材料を発光層に使用した有機ＥＬ素子の発光輝度および発光効率が高く、繰り返し使用時での安定性も優れていることを見いだし本発明を成すに至った。
【０００６】
【課題を解決するための手段】
本発明は、下記一般式［１］で示される有機エレクトロルミネッセンス素子用発光材料に関する。
一般式［１］
【０００７】
【化２】
［式中、Ｒ1〜Ｒ6は、それぞれ独立に−ＮＲ7Ｒ8 、（Ｒ7、Ｒ8は、置換もしく は未置換のアルキル基、置換もしくは未置換のアリール基を表わし、Ｒ7とＲ8が一体となってもよい。）、水素原子、ハロゲン原子、置換もしくは未置換のア ルキル基、置換もしくは未置換のアルコキシ基、置換もしくは未置換のアリールオキシ基、置換もしくは未置換のアルキルチオ基、置換もしくは未置換のアリールチオ基、置換もしくは未置換のアリール基を表わす（ただし、Ｒ1〜Ｒ6の２個以上は−ＮＲ7Ｒ8を示す。）。］
【０００９】
さらに、本発明は一般式［１］の少なくともＲ3とＲ6、または少なくともＲ1とＲ4が、−ＮＲ7 Ｒ8である上記発光材料に関する。
さらに、本発明はホスト材料と上記一般式［１］で示される化合物からなる有機エレクトロルミネッセンス素子用ドーピング発光材料に関する。
さらに、本発明は一対の電極間に発光層を含む複数層の有機化合物薄膜を形成した有機エレクトロルミネッセンス素子において、発光層が上記有機エレクトロルミネッセンス素子用発光材料を含有する層である有機エレクトロルミネッセンス素子に関する。
【００１０】
【発明の実施の形態】
本発明における一般式［１］で示される化合物のＲ1〜Ｒ6は、それぞれ独立に−ＮＲ7Ｒ8（Ｒ7、Ｒ8は、置換もしくは未置換のアルキル基、置換もしくは未置換のアリール基を表す。）、水素原子、ハロゲン原子、置換もしくは未置換のアルキル基、置換もしくは未置換のアルコキシ基、置換もしくは未置換のアリールオキシ基、置換もしくは未置換のアルキルチオ基、置換もしくは未置換のアリールチオ基、置換もしくは未置換のアリール基を表す。ただし、Ｒ1〜Ｒ6の２個以上は、−ＮＲ7Ｒ8である。また、少なくともＲ3とＲ6、またはＲ1とＲ4が、−ＮＲ7 Ｒ8であることが好ましい。
【００１１】
これらの具体例は、ハロゲン原子としては弗素、塩素、臭素、ヨウ素があり、置換もしくは未置換のアルキル基としては、メチル基、エチル基、プロピル基、ブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ステアリル基等の炭素数１〜２０の未置換のアルキル基の他、２−フェニルイソプロピル基、トリクロロメチル基、トリフルオロメチル基、ベンジル基、α−フェノキシベンジル基、α，α−ジメチルベンジル基、α，α−メチルフェニルベンジル基、α，α−ジトリフルオロメチルベンジル基、トリフェニルメチル基、α−ベンジルオキシベンジル基等の炭素数１〜２０のアルキル基の置換体がある。また、隣接するアルキル基同士が結合してシクロアルキル環を形成してもよい。
【００１２】
置換もしくは未置換のアルコキシル基としては、メトキシ基、エトキシ基、プロポキシ基、ｎ−ブトキシ基、ｔ−ブトキシ基、ｎ−オクチルオキシ基、ｔ−オクチルオキシ基等の炭素数１〜２０の未置換のアルコキシル基の他、１，１，１−テトラフルオロエトキシ基、フェノキシ基、ベンジルオキシ基、オクチルフェノキシ基等の炭素数１〜２０のアルコキシル基の置換体があり、置換もしくは未置換のアルキルチオ基の具体例とては、メチルチオ基、エチルチオ基、ｔｅｒｔ−ブチルチオ基、ヘキシルチオ基、オクチルチオ基、トリフルオロメチルチオ基等があり、置換もしくは未置換のアリール基としては、フェニル基、２−メチルフェニル基、３−メチルフェニル基、４−メチルフェニル基、４−エチルフェニル基、ビフェニル基、４−メチルビフェニル基、４−エチルビフェニル基、４−シクロヘキシルビフェニル基ターフェニル基、３，５−ジクロロフェニル基、ナフチル基、５−メチルナフチル基、アントリル基、ピレニル基等の芳香族炭素数６〜１８の置換もしくは未置換のアリール基があり、さらに、アリール基は、窒素原子、酸素原子およびまたは硫黄原子により芳香族炭素原子が置換されていてもよい。このようなアリール基としては、フラニル基、チオフェニル基、ピロール基、ピラニル基、チオピラニル基、ピリジニル基、チアゾリル基、イミダゾリール基、ピリミジニル基、ピリジニル基、トリアジニル基、インドリニル基、キノリル基、プリニル基等がある。
【００１３】
置換もしくは未置換のアリールオキシ基の具体例としては、フェノキシ基、ｐ−ニトロフェノキシ基、ｐ−ｔｅｒｔ−ブチルフェノキシ基、３−フルオロフェノキシ基、ペンタフルオロフェニル基、３−トリフルオロメチルフェノキシ基等があり、アリールチオ基の具体例とては、フェニルチオ基、ｐ−ニトロフェニルチオ基、ｐ−ｔｅｒｔ−ブチルフェニルチオ基、３−フルオロフェニルチオ基、ペンタフルオロフェニルチオ基、３−トリフルオロメチルフェニルチオ基等がある。
【００１４】
本発明における一般式［１］で表される化合物の−ＮＲ7Ｒ8（Ｒ7、Ｒ8は、置換もしくは未置換のアルキル基、置換もしくは未置換のアリール基を表す。）のアルキルアミノ基の具体例としては、ジメチルアミノ基、ジエチルアミノ基、ジプロピルアミノ基、ジブチルアミノ基、ベンジルアミノ基、ジベンジルアミノ基等のアルキルアミノ基があり、アリールアミノ基の具体例としては、フェニルメチルアミノ基、ジフェニルアミノ基、ジトリルアミノ基、ジビフェニルアミノ基、ジ（４−メチルビフェニル）アミノ基、ジ（３−メチルフェニル）アミノ基、ジ（４−メチルフェニル）アミノ基、ナフチルフェニルアミノ基等がある。
【００１５】
また、Ｒ7とＲ8が一体となって、モルホリン環、ピペラジン環、ピペリジン環、ベンゾピペラジン環、アクリジン環、フェナジン環、ピレニル環、カルバゾール環、ベンゾピラニル環、キサンテン環、チアゾリル環、チアジン環、ファノチアジン環等の飽和もしくは不飽和環を形成してもよい。
【００１６】
この化合物の中で、一般式［１］で表されるようなアリール基を有している置換基を持つ化合物は、ガラス転移点や融点が高くなり電界発光時における有機層中、有機層間もしくは、有機層と金属電極間で発生するジュール熱に対する耐性（耐熱性）が向上するので、有機ＥＬ素子の発光材料として使用した場合、高い発光輝度を示し、長時間発光させる際にも有利である。本発明の化合物は、これらの置換基に限定されるものではない。
【００１７】
本発明において、一般式［１］で表される化合物は例えば次のような方法で合成することが出来る。ニトロベンゼン溶媒中、ジブロモキノキサリンもしくはジヨードキノキサリンと芳香族ジアミン化合物を、炭酸カリウム、銅等の触媒と共に２００℃で５０時間反応させて、一般式［１］で示される芳香族アミン化合物を合成する。もしくは、ジアミノキノキサリンとハロゲン置換されたアリール誘導体を、１，３−ジメチル−２−イミダゾリジノン中、水酸化カリウム、銅触媒を用いて反応させることによっても同様に合成することができる。炭酸カリウムに代えて、炭酸ナトリウム、水酸化ナトリウム等を使用することが出来る。触媒としては、銅粉、塩化第一銅、錫、塩化第一錫等がある。溶媒は、Ｎ，Ｎ−ジメチルホルムアミド、ジメチルスルホキシド等がある。
【００１８】
一般式［１］で示される化合物の代表例を具体的に表１に例示するが、これらに限定されるものではない。
【００１９】
【表１】
有機ＥＬ素子は、陽極と陰極間に一層もしくは多層の有機化合物薄膜を形成した素子である。一層型の場合、陽極と陰極との間に発光層を設けている。発光層は、発光材料を含有し、それに加えて陽極から注入した正孔もしくは陰極から注入した電子を発光材料まで輸送させるために正孔注入材料もしくは電子注入材料を含有しても良い。多層型は、（陽極／正孔注入層／発光層／陰極）、（陽極／発光層／電子注入層／陰極）、（陽極／正孔注入層／発光層／電子注入層／陰極）の多層構成で積層した有機ＥＬ素子がある。本発明の一般式［１］で示される化合物は、固体状態において強い蛍光を持つ化合物であり電界発光性に優れているので、発光材料として発光層内で使用することができる。また、一般式［１］の化合物は、発光層内においてドーピング材料として発光層中にて最適の割合でドーピングすることにより、高い発光効率および発光波長の最適な選択が可能である。ここで、正孔注入層、発光層、もしくは電子注入層は、それぞれ二層以上で形成されても良い。
【００２７】
発光層のホスト材料に、ドーピング材料（ゲスト材料）として一般式［１］の化合物を使用して、発光輝度が高い有機ＥＬ素子を得ることもできる。一般式［１］の化合物は、発光層内において、ホスト材料に対して０．００１重量％〜５０重量％の範囲で含有されていることが望ましく、更には０．０１重量％〜１０重量％の範囲が効果的である。
【００２８】
一般式［１］の化合物と併せて使用できるホスト材料としては、キノリン金属錯体、オキサジアゾール、ベンゾチアゾール金属錯体、ベンゾオキサゾール金属錯体、ベンゾイミダゾール金属錯体、トリアゾール、イミダゾール、オキサゾール、オキサジアゾール、スチルベン、ブタジエン、ベンジジン型トリフェニルアミン、スチリルアミン型トリフェニルアミン、ジアミン型トリフェニルアミンフルオレノン、ジアミノアントラセン型トリフェニルアミン、ジアミノフェナントレン型トリフェニルアミン、アントラキノジメタン、ジフェノキノン、チアジアゾール、テトラゾール、ペリレンテトラカルボン酸、フレオレニリデンメタン、アントラキノジメタン、トリフェニレン、アントロン等とそれらの誘導体、および、ポリビニルカルバゾール、ポリシラン等の導電性高分子の高分子材料等がある。
【００２９】
一般式［１］と共に更なるドーピング材料を使用して発光色を変化させることも可能となる。一般式［１］と共に使用されるドーピング材料としては、アントラセン、ナフタレン、フェナントレン、ピレン、テトラセン、コロネン、クリセン、フルオレセイン、ペリレン、フタロペリレン、ナフタロペリレン、ペリノン、フタロペリノン、ナフタロペリノン、ジフェニルブタジエン、テトラフェニルブタジエン、クマリン、オキサジアゾール、アルダジン、ビスベンゾキサゾリン、ビススチリル、ピラジン、シクロペンタジエン、キノリン金属錯体、アミノキノリン金属錯体、イミン、ジフェニルエチレン、ビニルアントラセン、ジアミノカルバゾール、ピラン、チオピラン、ポリメチン、メロシアニン、イミダゾールキレート化オキシノイド化合物、キナクリドン、ルブレン等およびそれらの誘導体があるが、これらに限定されるものではない。
【００３０】
発光層には、発光材料およびドーピング材料に加えて、必要があれば正孔注入材料や電子注入材料を使用することもできる。
【００３１】
有機ＥＬ素子は、多層構造にすることにより、クエンチングによる輝度や寿命の低下を防ぐことができる。また、必要があれば、発光材料、ドーピング材料、キャリア注入を行う正孔注入材料や電子注入材料を二種類以上組み合わせて使用することも出来る。また、正孔注入層、発光層、電子注入層は、それぞれ二層以上の層構成により形成されても良く、正孔もしくは電子が効率よく電極から注入され、層中で輸送される素子構造が選択される。
【００３２】
有機ＥＬ素子の陽極に使用される導電性材料は、４ｅＶより大きな仕事関数を持つものが好適であり、炭素、アルミニウム、バナジウム、鉄、コバルト、ニッケル、タングステン、銀、金、白金、パラジウム等およびそれらの合金、ＩＴＯ基板、ＮＥＳＡ基板と称される酸化スズ、酸化インジウム等の酸化金属、さらにはポリチオフェンやポリピロール等の有機導電性樹脂が用いられる。
陰極に使用される導電性材料は、４ｅＶより小さな仕事関数を持つものが好適であり、マグネシウム、カルシウム、錫、鉛、チタニウム、イットリウム、リチウム、ルテニウム、マンガン等およびそれらの合金が用いられる。合金としては、マグネシウム／銀、マグネシウム／インジウム、リチウム／アルミニウム等が代表例として挙げられるが、これらに限定されるものではない。合金の比率は、加熱の温度、雰囲気、真空度により制御され適切な比率が選択される。陽極および陰極は、必要があれば二層以上の層構成により形成されていても良い。
【００３３】
有機ＥＬ素子では、効率良く発光させるために、少なくとも一方は素子の発光波長領域において充分透明であることが望ましい。また、基板も透明であることが望ましい。透明電極は、上記の導電性材料を使用して、蒸着やスパッタリング等の方法で所定の透光性を確保するように設定する。発光面の電極は、光透過率を１０％以上にすることが望ましい。
基板は、機械的、熱的強度を有し、透明であれば限定されるものではないが、例示すると、ガラス基板、ポリエチレン板、ポリエーテルサルフォン板、ポリプロピレン板等の透明性樹脂があげられる。
【００３４】
本発明に係わる有機ＥＬ素子の各層の形成は、真空蒸着、スパッタリング等の乾式成膜法やスピンコーティング、ディッピング等の湿式成膜法のいずれの方法を適用することができる。膜厚は特に限定されるものではないが、各層は適切な膜厚に設定する必要がある。膜厚が厚すぎると、一定の光出力を得るために大きな印加電圧が必要になり効率が悪くなる。膜厚が薄すぎるとピンホール等が発生して、電界を印加しても充分な発光輝度が得られない。通常の膜厚は５ｎｍから１０μｍの範囲が適しているが、１０ｎｍから０．２μｍの範囲がさらに好ましい。
【００３５】
湿式成膜法の場合、各層を形成する材料を、クロロホルム、テトラヒドロフラン、ジオキサン等の適切な溶媒に溶解または分散して薄膜を形成するが、その溶媒はいずれであっても良い。また、いずれの薄膜においても、成膜性向上、膜のピンホール防止等のため適切な樹脂や添加剤を使用しても良い。
このような樹脂としては、ポリスチレン、ポリカーボネート、ポリアリレート、ポリエステル、ポリアミド、ポリウレタン、ポリスルフォン、ポリメチルメタクリレート、ポリメチルアクリレート、セルロース等の絶縁性樹脂、ポリ−Ｎ−ビニルカルバゾール、ポリシラン等の光導電性樹脂、ポリチオフェン、ポリピロール等の導電性樹脂を挙げることができる。また、添加剤としては、酸化防止剤、紫外線吸収剤、可塑剤等を挙げることができる。
【００３６】
正孔注入材料としては、正孔を注入する能力を持ち、発光層または発光材料に対して優れた正孔注入効果を有し、発光層で生成した励起子の電子注入層または電子注入材料への移動を防止し、かつ薄膜形成能の優れた化合物が挙げられる。具体的には、フタロシアニン系化合物、ナフタロシアニン系化合物、ポルフィリン系化合物、オキサジアゾール、トリアゾール、イミダゾール、イミダゾロン、イミダゾールチオン、ピラゾリン、ピラゾロン、テトラヒドロイミダゾール、オキサゾール、オキサジアゾール、ヒドラゾン、アシルヒドラゾン、ポリアリールアルカン、スチルベン、ブタジエン、ベンジジン型トリフェニルアミン、スチリルアミン型トリフェニルアミン、ジアミン型トリフェニルアミン等と、それらの誘導体、およびポリビニルカルバゾール、ポリシラン、導電性高分子等の高分子材料等があるが、これらに限定されるものではない。
【００３７】
本発明の有機ＥＬ素子において使用できる正孔注入材料の中で、さらに効果的な正孔注入材料は、芳香族三級アミン誘導体もしくはフタロシアニン誘導体である。具体的には、トリフェニルアミン、トリトリルアミン、トリルジフェニルアミン、Ｎ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ジ（３−メチルフェニル）−１，１’−ビフェニル−４，４’−ジアミン、Ｎ，Ｎ，Ｎ’，Ｎ’−テトラ（４−メチルフェニル）−１，１’−ビフェニル−４，４’−ジアミン、Ｎ，Ｎ，Ｎ’，Ｎ’−テトラ（４−メチルフェニル）−１，１’−ビフェニル−４，４’−ジアミン、Ｎ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ジナフチル−１，１’−ビフェニル−４，４’−ジアミン、Ｎ，Ｎ’−ジ（メチルフェニル）−Ｎ，Ｎ’−ジ（４−ｎ−ブチルフェニル）−フェナントレン−９，１０−ジアミン、１，１−ビス［Ｎ，Ｎ−ジ（トリルアミノ）フェニル］シクロヘキサン等、もしくはこれらの芳香族三級アミン骨格を有したオリゴマーもしくはポリマー等があるが、これらに限定されるものではない。フタロシアニン（Ｐｃ）誘導体としては、Ｈ2Ｐｃ、ＣｕＰｃ、ＣｏＰｃ、ＮｉＰｃ、ＺｎＰｃ、ＰｄＰｃ、ＦｅＰｃ、ＭｎＰｃ、ＣｌＡｌＰｃ、ＣｌＧａＰｃ、ＣｌＩｎＰｃ、ＣｌＳｎＰｃ、Ｃｌ2ＳｉＰｃ、（ＨＯ）ＡｌＰｃ、（ＨＯ）ＧａＰｃ、ＶＯＰｃ、ＴｉＯＰｃ、ＭｏＯＰｃ、ＧａＰｃ−Ｏ−ＧａＰｃ等のフタロシアニン誘導体およびナフタロシアニン誘導体等があるが、これらに限定されるものではない。
【００３８】
電子注入材料としては、電子を注入する能力を持ち、発光層または発光材料に対して優れた電子注入効果を有し、発光層で生成した励起子の正孔注入層または正孔注入材料への移動を防止し、かつ薄膜形成能の優れた化合物が挙げられる。例えば、キノリン金属錯体、オキサジアゾール、ベンゾチアゾール金属錯体、ベンゾオキサゾール金属錯体、ベンゾイミダゾール金属錯体、フルオレノン、アントラキノジメタン、ジフェノキノン、チオピランジオキシド、オキサジアゾール、チアジアゾール、テトラゾール、ペリレンテトラカルボン酸、フレオレニリデンメタン、アントラキノジメタン、アントロン等とそれらの誘導体があるが、これらに限定されるものではない。また、正孔注入材料に電子受容物質を、電子注入材料に電子供与性物質を添加して増感させることもできる。
【００３９】
本発明の有機ＥＬ素子において、さらに効果的な電子注入材料は、金属錯体化合物もしくは含窒素五員環誘導体である。具体的には、金属錯体化合物としては、８−ヒドロキシキノリナートリチウム、ビス（８−ヒドロキシキノリナート）亜鉛、ビス（８−ヒドロキシキノリナート）銅、ビス（８−ヒドロキシキノリナート）マンガン、トリス（８−ヒドロキシキノリナート）アルミニウム、トリス（２−メチル−８−ヒドロキシキノリナート）アルミニウム、トリス（８−ヒドロキシキノリナート）ガリウム、ビス（１０−ヒドロキシベンゾ［ｈ］キノリナート）ベリリウム、ビス（１０−ヒドロキシベンゾ［ｈ］キノリナート）亜鉛、ビス（２−メチル−８−キノリナート）クロロガリウム、ビス（２−メチル−８−キノリナート）（ｏ−クレゾラート）ガリウム、ビス（２−メチル−８−キノリナート）（１−ナフトラート）アルミニウム、ビス（２−メチル−８−キノリナート）（２−ナフトラート）ガリウム等があるが、これらに限定されるものではない。また、含窒素五員誘導体としては、オキサゾール、チアゾール、オキサジアゾール、チアジアゾールもしくはトリアゾール誘導体が好ましい。
【００４０】
具体的には、２，５−ビス（１−フェニル）−１，３，４−オキサゾール、ジメチルＰＯＰＯＰ、２，５−ビス（１−フェニル）−１，３，４−チアゾール、２，５−ビス（１−フェニル）−１，３，４−オキサジアゾール、２−（４’−ｔｅｒｔ−ブチルフェニル）−５−(４”−ビフェニル)１，３，４−オキサジアゾール、２，５−ビス（１−ナフチル）−１，３，４−オキサジアゾール、１，４−ビス［２−(５−フェニルオキサジアゾリル)］ベンゼン、１，４−ビス［２−(５−フェニルオキサジアゾリル)］−２−ｔｅｒｔ−ブチルベンゼン、２−（４’−ｔｅｒｔ−ブチルフェニル）−５−(４”−ビフェニル)−１，３，４−チアジアゾール、２，５−ビス（１−ナフチル）−１，３，４−チアジアゾール、１，４−ビス［２−(５−フェニルチアジアゾリル)］ベンゼン、２−（４’−ｔｅｒｔ−ブチルフェニル）−５−(４”−ビフェニル)−１，３，４−トリアゾール、２，５−ビス（１−ナフチル）−１，３，４−トリアゾール、１，４−ビス［２−( ５−フェニルトリアゾリル)］ベンゼン等があるが、これらに限定されるものではない。
【００４１】
本有機ＥＬ素子においては、発光層中に、一般式［１］の化合物の他に、発光材料、ドーピング材料、正孔注入材料および電子注入材料の少なくとも１種が同一層に含有されてもよい。また、本発明により得られた有機ＥＬ素子の、温度、湿度、雰囲気等に対する安定性の向上のために、素子の表面に保護層を設けたり、シリコンオイル、樹脂等により素子全体を保護することも可能である。
【００４２】
以上のように、有機ＥＬ素子の発光層に本発明の化合物を用い、更には特定の正孔注入層もしくは電子注入層と組み合わせることにより、発光効率、最大発光輝度等の有機ＥＬ素子特性を改良することができた。また、この素子は熱や電流に対して非常に安定であり、さらには低い駆動電圧で実用的に使用可能の発光輝度が得られるため、従来まで大きな問題であった劣化も大幅に低下させることができた。
【００４３】
本発明の有機ＥＬ素子は、壁掛けテレビ等のフラットパネルディスプレイや、平面発光体として、複写機やプリンター等の光源、液晶ディスプレイや計器類等の光源、表示板、標識灯等へ応用が考えられ、その工業的価値は非常に大きい。
【００４４】
本発明の材料は、有機ＥＬ素子、電子写真感光体、光電変換素子、太陽電池、イメージセンサー等の分野においても使用できる。
【００４５】
【実施例】
以下、本発明を実施例に基づきさらに詳細に説明する。なお、説明中の部は重量部を表す。
化合物（２）の合成方法
１，３−ジメチル−２−イミダゾリジノン５０部中に、５，８−ジブロモキノキサリン７．２部、ｐ、ｐ’−ジトリルアミン１６．２部、および炭酸カリウム１２部、銅粉０．５部を入れ、２００℃にて５０時間加熱撹拌した。その後、５００部の水で希釈した。酢酸エチルで抽出を行い、濃縮して、シリカゲルを用いたカラムクロマトグラフィーにより精製を行ない白色の蛍光を有する粉末１２部を得た。ＦＤ−ＭＳよる分子量分析により、化合物（２）であることを確認した。
【００４６】
化合物（３）の合成方法
１，３−ジメチル−２−イミダゾリジノン５０部中に、５，８−ジブロモキノキサリン６．０部、１−ナフチル−フェニルアミン１２．２部、および炭酸カリウム８部、銅粉０．５部を入れ、２００℃にて５０時間加熱撹拌した。その後、５００部の水で希釈した。酢酸エチルで抽出を行い、濃縮して、シリカゲルを用いたカラムクロマトグラフィーにより精製を行ない白色の蛍光を有する粉末１３部を得た。ＦＤ−ＭＳよる分子量分析により、化合物（３）であることを確認した。
【００４８】
実施例１
洗浄したＩＴＯ電極付きガラス板上に、発光材料として表１の化合物（２）、２，５−ビス（１−ナフチル）−１，３，４−オキサジアゾール、ポリカーボネート樹脂（帝人化成：パンライトＫ−１３００）を５：３：２の重量比でテトラヒドロフランに溶解させ、スピンコーティング法により膜厚１００ｎｍの発光層を得た。その上に、マグネシウムと銀を１０：１で混合した合金で膜厚１５０ｎｍの電極を形成して有機ＥＬ素子を得た。この素子の発光特性は、直流電圧５Ｖで１００（ｃｄ／ｍ2）、最高輝度１０００（ｃｄ／ｍ2）、発光効率０．６０（ｌｍ／Ｗ）の発光が得られた。
【００４９】
実施例２
洗浄したＩＴＯ電極付きガラス板上に、Ｎ，Ｎ'―ジ（３―メチルフェニル） ―Ｎ，Ｎ'―ジフェニル―１，１―ビフェニル-４，４―ジアミン（ＴＰＤ）を真空蒸着して、膜厚２０ｎｍの正孔注入層を得た。次いで、化合物（２）を蒸着し膜厚４０ｎｍの発光層を作成し、トリス（８−ヒドロキシキノリン）アルミニウム錯体（Ａｌｑ３）を蒸着し、膜厚３０ｎｍの電子注入層を得た。その上に、マグネシウムと銀を１０：１で混合した合金で膜厚１００ｎｍの電極を形成して有機ＥＬ素子を得た。正孔注入層および発光層は１０-6Ｔｏｒｒの真空中で、基板温度室温の条件下で蒸着した。この素子は直流電圧５Ｖで発光輝度１１０（ｃｄ／ｍ2）、最大発光輝度１１０００（ｃｄ／ｍ2）、５Ｖの時の発光効率１．１（ｌｍ／Ｗ）の青色発光が得られた。
【００５１】
実施例４
洗浄したＩＴＯ電極付きガラス板上に、化合物（３）を真空蒸着して、膜厚５０ｎｍの正孔注入型発光層を得た。次いで、ビス（２−メチル−８−キノリナート）（１−ナフトラート）ガリウム錯体を真空蒸着して膜厚１０ｎｍの電子注入層を作成し、その上に、マグネシウムと銀を１０：１で混合した合金で膜厚１００ｎｍの電極を形成して有機ＥＬ素子を得た。発光層および電子注入層は１０- 6Ｔｏｒｒの真空中で、基板温度室温の条件下で蒸着した。この素子は、直流電 圧５Ｖで３００（ｃｄ／ｍ2）、最高輝度１０２００（ｃｄ／ｍ2）、発光効率１．６０（ｌｍ／Ｗ）の発光が得られた。
【００５２】
実施例７〜１３、１５〜１７、１９、２０
洗浄したＩＴＯ電極付きガラス板上に、下記化学構造で示される化合物（２６）を真空蒸着して、膜厚２０ｎｍに正孔注入層を形成した。次いで、発光材料として、表１の化合物を真空蒸着して膜厚２０ｎｍの発光層を得た。次いで、ビス（２−メチル−８−キノリナート）（１−ナフトラート）ガリウム錯体を真空蒸着して膜厚１０ｎｍの電子注入層を作成し、その上に、マグネシウムと銀を１０：１で混合した合金で膜厚１００ｎｍの電極を形成して有機ＥＬ素子を得た。正孔注入層および発光層は１０-6Ｔｏｒｒの真空中で、基板温度室温の条件下で蒸着した。この素子の発光特性を表２に示す。ここでの発光輝度は、直流電圧５Ｖ印可時の輝度である。本実施例の有機ＥＬ素子は、全て最高輝度１００００（ｃｄ／ｍ2）以上の高輝度特性を有し、また、青色から緑色の発光色を得ることができた。
【００５３】
化合物（２６）
【００５４】
【化３】
【表２】
実施例２１
洗浄したＩＴＯ電極付きガラス板上に、４、４’、４”−トリス［Ｎ−（３−メチルフェニル）−Ｎ−フェニルアミノ］トリフェニルアミンを真空蒸着して、膜厚４０ｎｍの正孔注入層を得た。次いで、４，４’−ビス［Ｎ−（１−ナフチル）−Ｎ−フェニルアミノ］ビフェニル（α−ＮＰＤ）を真空蒸着して、膜厚１０ｎｍの第二正孔注入層を得た。さらに、化合物（２）を真空蒸着して、膜厚３０ｎｍの発光層を作成し、さらにビス（２−メチル−８−ヒドロキシキノリナト）（１−フェノラート）ガリウム錯体を真空蒸着して膜厚３０ｎｍの電子注入層を作成し、その上に、アルミニウムとリチウムを２５：１で混合した合金で膜厚１５０ｎｍの電極を形成して、有機ＥＬ素子を得た。正孔注入層および発光層は１０-6Ｔｏｒｒの真空中で、基板温度室温の条件下で蒸着した。この素子は、直流電圧５Ｖで発光輝度６１０（ｃｄ／ｍ2）、最大発光輝度２９０００（ｃｄ／ ｍ2）、発光効率２．８（ｌｍ／Ｗ）の青色発光が得られた。
【００５８】
実施例２３
４、４’、４”−トリス［Ｎ−（３−メチルフェニル）−Ｎ−フェニルアミノ］トリフェニルアミンの代わりに無金属フタロシアニンの膜厚２０ｎｍの正孔注入層を設ける以外は、実施例２１と同様の方法で有機ＥＬ素子を作製した。この素子は、直流電圧５Ｖで２２０（ｃｄ／ｍ2）、最高輝度１２０００（ｃｄ／ｍ 2）、発光効率１．１０（ｌｍ／Ｗ）の青緑色発光が得られた。
【００５９】
実施例２４
発光層として、化合物（１２）：化合物（２７）を１：１００の割合で蒸着した膜厚１０ｎｍの正孔注入層を設ける以外は、実施例２１と同様の方法で有機ＥＬ素子を作製した。この素子は、直流電圧５Ｖで１０００（ｃｄ／ｍ2）、最高 輝度１８０００（ｃｄ／ｍ2）、発光効率１．５０（ｌｍ／Ｗ）の青緑色発光が 得られた。
【００６０】
化合物（２７）
【００６１】
【化４】
本実施例で示された有機ＥＬ素子は、二層型以上の素子構成において、最大発光輝度１００００（ｃｄ／ｍ2）以上の発光が得られ、高い発光効率を得る ことができた。本実施例で示された有機ＥＬ素子について、３（ｍＡ／ｃｍ2） で連続発光させたところ、１０００時間以上安定な発光を観測することができた。
本発明の有機ＥＬ素子は発光効率、発光輝度の向上と長寿命化を達成するものであり、併せて使用される発光材料、ドーピング材料、正孔注入材料、電子注入材料、増感剤、樹脂、電極材料等および素子作製方法を限定するものではない。
【００６４】
【発明の効果】
本発明の有機ＥＬ用発光材料を発光材料として使用した有機ＥＬ素子は、従来に比べて高い発光効率で高輝度の発光を示し、長寿命の有機ＥＬ素子を得ることができた。[0001]
[Industrial application fields]
The present invention relates to a light-emitting material for organic electroluminescence (EL) elements and a high-luminance light-emitting element used for flat light sources and displays.
[0002]
[Prior art]
An EL element using an organic substance is considered to be promising for use as an inexpensive large-area full-color display element of a solid light emitting type, and many developments have been made. In general, an EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the layer. In light emission, when an electric field is applied between both electrodes, electrons are injected from the cathode side and holes are injected from the anode side. Furthermore, the electrons are recombined with holes in the light emitting layer, and energy is emitted as light when the energy level returns from the conduction band to the valence band.
[0003]
Conventional organic EL elements have a higher driving voltage and lower light emission luminance and light emission efficiency than inorganic EL elements. Further, the characteristic deterioration has been remarkably not put into practical use.
In recent years, organic EL devices in which thin films containing organic compounds with high fluorescence quantum efficiency that emit light at a low voltage of 10 V or less have been reported and attracted attention (Applied Physics Letters, Vol. 51, page 913). 1987).
This method uses a metal chelate complex as a light emitting layer and an amine compound as a hole injection layer to obtain a high luminance green light emission. The luminance is several thousand cd / m 2 at a direct current voltage of 6 to 7 V, maximum. The luminous efficiency is 1.5 lm / W, and the performance is close to the practical range.
[0004]
However, the organic EL devices up to now have improved light emission intensity due to the improvement of the structure, but do not yet have sufficient light emission luminance. Moreover, it has a big problem that it is inferior in stability during repeated use. This is because, for example, metal chelate complexes such as tris (8-hydroxyquinolinate) aluminum complex are chemically unstable during electroluminescence, poor adhesion to the cathode, and greatly deteriorated in a short time of light emission. It was. For the above reasons, in order to develop an organic EL device having high luminous brightness and luminous efficiency and excellent stability during repeated use, the development of a light-emitting material with excellent luminous ability and durability has been developed. It is desired.
[0005]
[Problems to be solved by the invention]
An object of the present invention is to provide an organic EL device having high emission luminance and excellent stability in repeated use. As a result of intensive studies by the present inventors, the organic EL device using the light emitting material for the organic EL device represented by the general formula [1] in the light emitting layer has high light emission luminance and light emission efficiency, and stability during repeated use. The inventors have found that the present invention is excellent and have come to make the present invention.
[0006]
[Means for Solving the Problems]
The present invention relates to a light emitting material for an organic electroluminescence device represented by the following general formula [1].
General formula [1]
[0007]
[Chemical 2]
[Wherein, R 1 to R 6 each independently represent —NR 7 R 8 , (R 7 and R 8 represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and R 7 And R 8 may be combined.), Hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted An alkylthio group, a substituted or unsubstituted arylthio group, or a substituted or unsubstituted aryl group is represented (however, two or more of R 1 to R 6 represent —NR 7 R 8 ). ]
[0009]
Furthermore, the present invention relates to the above light-emitting material in which at least R 3 and R 6 or at least R 1 and R 4 in the general formula [1] are —NR 7 R 8 .
Furthermore, the present invention relates to a doped luminescent material for an organic electroluminescence device comprising a host material and a compound represented by the above general formula [1].
Furthermore, the present invention relates to an organic electroluminescent device in which a plurality of organic compound thin films including a light emitting layer are formed between a pair of electrodes, wherein the light emitting layer is a layer containing the light emitting material for the organic electroluminescent device. About.
[0010]
DETAILED DESCRIPTION OF THE INVENTION
R 1 to R 6 of the compound represented by the general formula [1] in the present invention are each independently —NR 7 R 8 (R 7 and R 8 are a substituted or unsubstituted alkyl group, substituted or unsubstituted aryl, Represents a hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted An arylthio group represents a substituted or unsubstituted aryl group. However, two or more of R 1 to R 6 are —NR 7 R 8 . Moreover, it is preferable that at least R 3 and R 6 , or R 1 and R 4 are —NR 7 R 8 .
[0011]
Specific examples thereof include fluorine, chlorine, bromine, and iodine as halogen atoms, and methyl, ethyl, propyl, butyl, sec-butyl, and tert-butyl as substituted or unsubstituted alkyl groups. Group, pentyl group, hexyl group, heptyl group, octyl group, stearyl group and other unsubstituted alkyl groups having 1 to 20 carbon atoms, 2-phenylisopropyl group, trichloromethyl group, trifluoromethyl group, benzyl group, α-phenoxybenzyl group, α, α-dimethylbenzyl group, α, α-methylphenylbenzyl group, α, α-ditrifluoromethylbenzyl group, triphenylmethyl group, α-benzyloxybenzyl group, etc. There are 20 alkyl group substitutions. Further, adjacent alkyl groups may be bonded to form a cycloalkyl ring.
[0012]
As the substituted or unsubstituted alkoxyl group, an unsubstituted C1-C20 such as methoxy group, ethoxy group, propoxy group, n-butoxy group, t-butoxy group, n-octyloxy group, t-octyloxy group, etc. In addition to the alkoxyl group, there is a substituted product of an alkoxyl group having 1 to 20 carbon atoms such as 1,1,1-tetrafluoroethoxy group, phenoxy group, benzyloxy group, octylphenoxy group, etc., and a substituted or unsubstituted alkylthio group Specific examples thereof include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group, an octylthio group, a trifluoromethylthio group, and the like, and examples of the substituted or unsubstituted aryl group include a phenyl group and a 2-methylphenyl group 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, biphenyl group, -6-18 aromatic carbon atoms such as methylbiphenyl group, 4-ethylbiphenyl group, 4-cyclohexylbiphenyl group terphenyl group, 3,5-dichlorophenyl group, naphthyl group, 5-methylnaphthyl group, anthryl group, pyrenyl group The aryl group may be substituted with an aromatic carbon atom by a nitrogen atom, an oxygen atom and / or a sulfur atom. Such aryl groups include furanyl, thiophenyl, pyrrole, pyranyl, thiopyranyl, pyridinyl, thiazolyl, imidazolyl, pyrimidinyl, pyridinyl, triazinyl, indolinyl, quinolyl, purinyl Etc.
[0013]
Specific examples of the substituted or unsubstituted aryloxy group include phenoxy group, p-nitrophenoxy group, p-tert-butylphenoxy group, 3-fluorophenoxy group, pentafluorophenyl group, 3-trifluoromethylphenoxy group, and the like. Specific examples of the arylthio group include phenylthio group, p-nitrophenylthio group, p-tert-butylphenylthio group, 3-fluorophenylthio group, pentafluorophenylthio group, and 3-trifluoromethylphenyl group. There are thio groups and the like.
[0014]
An alkylamino group of —NR 7 R 8 (R 7 , R 8 represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group) of the compound represented by the general formula [1] in the present invention. Specific examples of these include alkylamino groups such as dimethylamino group, diethylamino group, dipropylamino group, dibutylamino group, benzylamino group, and dibenzylamino group. Specific examples of arylamino groups include phenylmethylamino Group, diphenylamino group, ditolylamino group, dibiphenylamino group, di (4-methylbiphenyl) amino group, di (3-methylphenyl) amino group, di (4-methylphenyl) amino group, naphthylphenylamino group, etc. is there.
[0015]
R 7 and R 8 are combined to form a morpholine ring, piperazine ring, piperidine ring, benzopiperazine ring, acridine ring, phenazine ring, pyrenyl ring, carbazole ring, benzopyranyl ring, xanthene ring, thiazolyl ring, thiazine ring, A saturated or unsaturated ring such as a fanothiazine ring may be formed.
[0016]
Among these compounds, a compound having a substituent having an aryl group represented by the general formula [1] has a high glass transition point and melting point, and the organic layer, organic layer or Since resistance to Joule heat generated between the organic layer and the metal electrode (heat resistance) is improved, when used as a light-emitting material of an organic EL element, it exhibits high emission luminance and is advantageous when emitting light for a long time. . The compounds of the present invention are not limited to these substituents.
[0017]
In the present invention, the compound represented by the general formula [1] can be synthesized, for example, by the following method. In an nitrobenzene solvent, dibromoquinoxaline or diiodoquinoxaline and an aromatic diamine compound are reacted with a catalyst such as potassium carbonate or copper at 200 ° C. for 50 hours to synthesize an aromatic amine compound represented by the general formula [1]. Alternatively, it can be similarly synthesized by reacting diaminoquinoxaline with a halogen-substituted aryl derivative in 1,3-dimethyl-2-imidazolidinone using potassium hydroxide or a copper catalyst. Instead of potassium carbonate, sodium carbonate, sodium hydroxide, or the like can be used. Examples of the catalyst include copper powder, cuprous chloride, tin, and stannous chloride. Examples of the solvent include N, N-dimethylformamide and dimethyl sulfoxide.
[0018]
Although the typical example of a compound shown by General formula [1] is specifically illustrated in Table 1, it is not limited to these.
[0019]
[Table 1]
An organic EL element is an element in which a single-layer or multilayer organic compound thin film is formed between an anode and a cathode. In the case of the single layer type, a light emitting layer is provided between the anode and the cathode. The light emitting layer contains a light emitting material, and may further contain a hole injecting material or an electron injecting material in order to transport holes injected from the anode or electrons injected from the cathode to the light emitting material. The multilayer type is a multilayer of (anode / hole injection layer / light emitting layer / cathode), (anode / light emitting layer / electron injection layer / cathode), and (anode / hole injection layer / light emitting layer / electron injection layer / cathode). There are organic EL elements stacked in a configuration. Since the compound represented by the general formula [1] of the present invention is a compound having strong fluorescence in a solid state and excellent in electroluminescence, it can be used as a light emitting material in a light emitting layer. In addition, the compound of the general formula [1] can be optimally selected for high luminous efficiency and emission wavelength by doping the light emitting layer as a doping material at an optimum ratio in the light emitting layer. Here, each of the hole injection layer, the light emitting layer, and the electron injection layer may be formed of two or more layers.
[0027]
An organic EL device having high emission luminance can be obtained by using the compound of the general formula [1] as a doping material (guest material) for the host material of the light emitting layer. The compound of the general formula [1] is desirably contained in the light emitting layer in the range of 0.001% by weight to 50% by weight with respect to the host material, and further 0.01% by weight to 10% by weight. The range of is effective.
[0028]
Host materials that can be used in combination with the compound of the general formula [1] include quinoline metal complex, oxadiazole, benzothiazole metal complex, benzoxazole metal complex, benzimidazole metal complex, triazole, imidazole, oxazole, oxadiazole, Stilbene, butadiene, benzidine type triphenylamine, styrylamine type triphenylamine, diamine type triphenylamine fluorenone, diaminoanthracene type triphenylamine, diaminophenanthrene type triphenylamine, anthraquinodimethane, diphenoquinone, thiadiazole, tetrazole, perylene Tetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, triphenylene, anthrone, and their derivatives, and polyvinylcarba Lumpur, polymeric materials such conductive polymers polysilane.
[0029]
It is also possible to change the emission color using further doping materials with the general formula [1]. The doping materials used together with the general formula [1] include anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene, phthaloperylene, naphthaloperylene, perinone, phthaloperinone, naphthaloperinone, diphenylbutadiene, tetraphenylbutadiene, coumarin. , Oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine, cyclopentadiene, quinoline metal complex, aminoquinoline metal complex, imine, diphenylethylene, vinylanthracene, diaminocarbazole, pyran, thiopyran, polymethine, merocyanine, imidazole chelation Oxinoid compounds, quinacridone, rubrene, etc. and their derivatives, but are not limited to these Not.
[0030]
In addition to the light emitting material and the doping material, if necessary, a hole injection material or an electron injection material can be used for the light emitting layer.
[0031]
By making the organic EL element have a multi-layer structure, it is possible to prevent a decrease in luminance and lifetime due to quenching. If necessary, a light emitting material, a doping material, a hole injecting material for injecting carriers, or an electron injecting material can be used in combination. In addition, the hole injection layer, the light emitting layer, and the electron injection layer may each be formed of two or more layers, and there is an element structure in which holes or electrons are efficiently injected from the electrode and transported in the layer. Selected.
[0032]
The conductive material used for the anode of the organic EL element is preferably one having a work function larger than 4 eV, such as carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium, and the like. These alloys, ITO substrates, metal oxides such as tin oxide and indium oxide called NESA substrates, and organic conductive resins such as polythiophene and polypyrrole are used.
A conductive material used for the cathode is preferably one having a work function smaller than 4 eV, and magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, and the like and alloys thereof are used. Examples of alloys include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but are not limited thereto. The ratio of the alloy is controlled by the heating temperature, atmosphere, and degree of vacuum, and an appropriate ratio is selected. If necessary, the anode and the cathode may be formed of two or more layers.
[0033]
In the organic EL element, in order to emit light efficiently, it is desirable that at least one of the elements is sufficiently transparent in the light emission wavelength region of the element. The substrate is also preferably transparent. The transparent electrode is set so as to ensure a predetermined translucency by a method such as vapor deposition or sputtering using the conductive material. The electrode on the light emitting surface preferably has a light transmittance of 10% or more.
The substrate has mechanical and thermal strength and is not limited as long as it is transparent. Examples thereof include transparent resins such as a glass substrate, a polyethylene plate, a polyethersulfone plate, and a polypropylene plate. .
[0034]
Formation of each layer of the organic EL device according to the present invention can be performed by any of dry film forming methods such as vacuum deposition and sputtering and wet film forming methods such as spin coating and dipping. The film thickness is not particularly limited, but each layer needs to be set to an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too thin, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied. The normal film thickness is suitably in the range of 5 nm to 10 μm, but more preferably in the range of 10 nm to 0.2 μm.
[0035]
In the case of the wet film-forming method, the material for forming each layer is dissolved or dispersed in an appropriate solvent such as chloroform, tetrahydrofuran, dioxane or the like to form a thin film, and any solvent may be used. In any thin film, an appropriate resin or additive may be used in order to improve film formability and prevent pinholes in the film.
Examples of such resins include insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, and cellulose, and photoconductivity such as poly-N-vinylcarbazole and polysilane. Examples thereof include conductive resins such as conductive resins, polythiophene, and polypyrrole. Examples of the additive include an antioxidant, an ultraviolet absorber, and a plasticizer.
[0036]
As a hole injection material, it has the ability to inject holes, has an excellent hole injection effect for the light emitting layer or light emitting material, and excitons generated in the light emitting layer to the electron injection layer or electron injection material And a compound having an excellent ability to form a thin film. Specifically, phthalocyanine compounds, naphthalocyanine compounds, porphyrin compounds, oxadiazole, triazole, imidazole, imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole, hydrazone, acyl hydrazone, poly Aryl alkane, stilbene, butadiene, benzidine type triphenylamine, styrylamine type triphenylamine, diamine type triphenylamine, and their derivatives, and polymer materials such as polyvinylcarbazole, polysilane, and conductive polymers However, it is not limited to these.
[0037]
Among the hole injection materials that can be used in the organic EL device of the present invention, a more effective hole injection material is an aromatic tertiary amine derivative or a phthalocyanine derivative. Specifically, triphenylamine, tolylamine, tolyldiphenylamine, N, N′-diphenyl-N, N′-di (3-methylphenyl) -1,1′-biphenyl-4,4′-diamine, N , N, N ′, N′-tetra (4-methylphenyl) -1,1′-biphenyl-4,4′-diamine, N, N, N ′, N′-tetra (4-methylphenyl) -1 , 1′-biphenyl-4,4′-diamine, N, N′-diphenyl-N, N′-dinaphthyl-1,1′-biphenyl-4,4′-diamine, N, N′-di (methylphenyl) ) -N, N′-di (4-n-butylphenyl) -phenanthrene-9,10-diamine, 1,1-bis [N, N-di (tolylamino) phenyl] cyclohexane, or the like Oligomer or polymer having a secondary amine skeleton There are, but not limited thereto. Examples of phthalocyanine (Pc) derivatives include H 2 Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl 2 SiPc, (HO) AlPc, (HO) GaPc, VOPc, Examples include, but are not limited to, phthalocyanine derivatives such as TiOPc, MoOPc, GaPc-O-GaPc, and naphthalocyanine derivatives.
[0038]
As an electron injection material, it has the ability to inject electrons, has an excellent electron injection effect for the light emitting layer or the light emitting material, and excitons generated in the light emitting layer are injected into the hole injection layer or the hole injection material. Examples thereof include compounds that prevent migration and have excellent thin film forming ability. For example, quinoline metal complex, oxadiazole, benzothiazole metal complex, benzoxazole metal complex, benzimidazole metal complex, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxadiazole, thiadiazole, tetrazole, perylenetetracarboxylic Acids, fluorenylidene methane, anthraquinodimethane, anthrone and the like and derivatives thereof are not limited thereto. Further, sensitization can be performed by adding an electron accepting substance to the hole injecting material and an electron donating substance to the electron injecting material.
[0039]
In the organic EL device of the present invention, a more effective electron injection material is a metal complex compound or a nitrogen-containing five-membered ring derivative. Specifically, as the metal complex compound, 8-hydroxyquinolinate lithium, bis (8-hydroxyquinolinate) zinc, bis (8-hydroxyquinolinate) copper, bis (8-hydroxyquinolinate) manganese , Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] quinolinato) beryllium Bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (o-cresolate) gallium, bis (2-methyl- 8-quinolinato) (1-naphtholate) aluminum, bis (2-mes There is Le-8-quinolinate) (2-naphtholato) gallium and the like, but is not limited thereto. Further, as the nitrogen-containing five-membered derivative, an oxazole, thiazole, oxadiazole, thiadiazole or triazole derivative is preferable.
[0040]
Specifically, 2,5-bis (1-phenyl) -1,3,4-oxazole, dimethyl POPOP, 2,5-bis (1-phenyl) -1,3,4-thiazole, 2,5- Bis (1-phenyl) -1,3,4-oxadiazole, 2- (4′-tert-butylphenyl) -5- (4 ″ -biphenyl) 1,3,4-oxadiazole, 2,5 -Bis (1-naphthyl) -1,3,4-oxadiazole, 1,4-bis [2- (5-phenyloxadiazolyl)] benzene, 1,4-bis [2- (5-phenyloxa) Diazolyl)]-2-tert-butylbenzene, 2- (4′-tert-butylphenyl) -5- (4 ″ -biphenyl) -1,3,4-thiadiazole, 2,5-bis (1-naphthyl) ) -1,3,4-thiadiazole, 1,4-bis [2- (5-fur Nilthiadiazolyl)] benzene, 2- (4′-tert-butylphenyl) -5- (4 ″ -biphenyl) -1,3,4-triazole, 2,5-bis (1-naphthyl) -1, Examples include, but are not limited to, 3,4-triazole, 1,4-bis [2- (5-phenyltriazolyl)] benzene.
[0041]
In the organic EL element, in the light emitting layer, in addition to the compound of the general formula [1], at least one of a light emitting material, a doping material, a hole injection material, and an electron injection material may be contained in the same layer. . In order to improve the stability of the organic EL device obtained by the present invention with respect to temperature, humidity, atmosphere, etc., a protective layer is provided on the surface of the device, or the entire device is protected by silicon oil, resin, etc. Is also possible.
[0042]
As described above, by using the compound of the present invention in the light emitting layer of the organic EL device, and further combining with a specific hole injection layer or electron injection layer, the organic EL device characteristics such as light emission efficiency and maximum light emission luminance are improved. We were able to. In addition, this element is extremely stable against heat and current, and can be used for light emission brightness that can be used practically at a low driving voltage, so that the degradation that has been a major problem until now is greatly reduced. I was able to.
[0043]
The organic EL device of the present invention can be applied to flat panel displays such as wall-mounted TVs, flat light emitters, light sources such as copiers and printers, light sources such as liquid crystal displays and instruments, display boards, and indicator lights. The industrial value is very large.
[0044]
The material of the present invention can also be used in the fields of organic EL devices, electrophotographic photoreceptors, photoelectric conversion devices, solar cells, image sensors and the like.
[0045]
【Example】
Hereinafter, the present invention will be described in more detail based on examples. In addition, the part in description represents a weight part.
Synthesis Method of Compound (2) In 50 parts of 1,3-dimethyl-2-imidazolidinone, 7.2 parts of 5,8-dibromoquinoxaline, 16.2 parts of p, p'-ditolylamine, and 12 parts of potassium carbonate Then, 0.5 part of copper powder was added, and the mixture was heated and stirred at 200 ° C. for 50 hours. Thereafter, it was diluted with 500 parts of water. Extraction with ethyl acetate, concentration, and purification by column chromatography using silica gel gave 12 parts of a powder having white fluorescence. It was confirmed to be the compound (2) by molecular weight analysis by FD-MS.
[0046]
Synthesis Method of Compound (3) In 50 parts of 1,3-dimethyl-2-imidazolidinone, 6.0 parts of 5,8-dibromoquinoxaline, 12.2 parts of 1-naphthyl-phenylamine, and 8 parts of potassium carbonate Then, 0.5 part of copper powder was added, and the mixture was heated and stirred at 200 ° C. for 50 hours. Thereafter, it was diluted with 500 parts of water. Extraction with ethyl acetate, concentration, and purification by column chromatography using silica gel gave 13 parts of a powder having white fluorescence. It was confirmed to be the compound (3) by molecular weight analysis by FD-MS.
[0048]
Example 1
On the washed glass plate with ITO electrode, the compound (2) in Table 1 as a luminescent material, 2,5-bis (1-naphthyl) -1,3,4-oxadiazole, polycarbonate resin (Teijin Chemicals: Panlite) K-1300) was dissolved in tetrahydrofuran at a weight ratio of 5: 3: 2, and a light emitting layer having a thickness of 100 nm was obtained by a spin coating method. On top of that, an electrode having a thickness of 150 nm was formed from an alloy in which magnesium and silver were mixed at a ratio of 10: 1 to obtain an organic EL element. With respect to the light emission characteristics of this device, light emission of 100 (cd / m 2 ), a maximum luminance of 1000 (cd / m 2 ), and a light emission efficiency of 0.60 (lm / W) was obtained at a DC voltage of 5V.
[0049]
Example 2
N, N′-di (3-methylphenyl) -N, N′-diphenyl-1,1-biphenyl-4,4-diamine (TPD) was vacuum-deposited on the cleaned glass plate with an ITO electrode, A hole injection layer having a thickness of 20 nm was obtained. Subsequently, the compound (2) was vapor-deposited to form a light-emitting layer having a thickness of 40 nm, and tris (8-hydroxyquinoline) aluminum complex (Alq3) was vapor-deposited to obtain an electron injection layer having a thickness of 30 nm. On top of that, an electrode having a thickness of 100 nm was formed from an alloy in which magnesium and silver were mixed at a ratio of 10: 1 to obtain an organic EL element. The hole injection layer and the light emitting layer were deposited in a vacuum of 10 −6 Torr at a substrate temperature of room temperature. This device obtained blue light emission at a direct current voltage of 5V with an emission luminance of 110 (cd / m 2 ), a maximum emission luminance of 11000 (cd / m 2 ), and an emission efficiency of 1.1 (lm / W) at 5V.
[0051]
Example 4
Compound (3) was vacuum-deposited on the washed glass plate with an ITO electrode to obtain a 50 nm-thick hole injection type light emitting layer. Next, a bis (2-methyl-8-quinolinato) (1-naphtholate) gallium complex is vacuum-deposited to form an electron injection layer having a thickness of 10 nm, on which magnesium and silver are mixed at a ratio of 10: 1. Thus, an electrode having a film thickness of 100 nm was formed to obtain an organic EL device. Emitting layer and the electron injection layer 10 - of 6 Torr in vacuum, and deposited under a substrate temperature of room temperature. This device emitted light of 300 (cd / m 2 ), maximum luminance of 10200 (cd / m 2 ), and luminous efficiency of 1.60 (lm / W) at a DC voltage of 5V.
[0052]
Examples 7-13, 15-17, 19, 20
On the washed glass plate with an ITO electrode, the compound (26) represented by the following chemical structure was vacuum-deposited to form a hole injection layer having a thickness of 20 nm. Subsequently, the compound of Table 1 was vacuum-deposited as a luminescent material, and the light emitting layer with a film thickness of 20 nm was obtained. Next, a bis (2-methyl-8-quinolinato) (1-naphtholate) gallium complex is vacuum-deposited to form an electron injection layer having a thickness of 10 nm, on which magnesium and silver are mixed at a ratio of 10: 1. Thus, an electrode having a film thickness of 100 nm was formed to obtain an organic EL device. The hole injection layer and the light emitting layer were deposited in a vacuum of 10 −6 Torr at a substrate temperature of room temperature. The light emission characteristics of this element are shown in Table 2. The light emission luminance here is the luminance when a DC voltage of 5 V is applied. All of the organic EL devices of this example had a high luminance characteristic with a maximum luminance of 10,000 (cd / m 2 ) or more, and a blue to green emission color could be obtained.
[0053]
Compound (26)
[0054]
[Chemical 3]
[Table 2]
Example 21
4,4 ′, 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine is vacuum-deposited on a cleaned glass plate with an ITO electrode to inject holes with a thickness of 40 nm. Next, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (α-NPD) was vacuum-deposited to form a second hole injection layer having a thickness of 10 nm. Further, the compound (2) was vacuum-deposited to prepare a light-emitting layer having a thickness of 30 nm, and a bis (2-methyl-8-hydroxyquinolinato) (1-phenolate) gallium complex was vacuum-deposited. An electron injection layer having a thickness of 30 nm was prepared, and an electrode having a thickness of 150 nm was formed from an alloy in which aluminum and lithium were mixed at a ratio of 25: 1 to obtain an organic EL device. layer in a vacuum of 10 -6 Torr It was deposited under the conditions of a substrate temperature of room temperature. The device is a direct current voltage of 5V in emission luminance 610 (cd / m 2), the maximum emission luminance 29000 (cd / m 2), luminous efficiency 2.8 (lm / W) Of blue light emission was obtained.
[0058]
Example 23
Example 21 except that a 20 nm thick hole injection layer of metal-free phthalocyanine is provided instead of 4,4 ′, 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine An organic EL device was manufactured in the same manner as described above, and this device was a blue voltage of 220 (cd / m 2 ), a maximum luminance of 12000 (cd / m 2 ) at a DC voltage of 5 V, and a luminous efficiency of 1.10 (lm / W). Green emission was obtained.
[0059]
Example 24
An organic EL device was produced in the same manner as in Example 21 except that a 10 nm-thick hole injection layer in which compound (12): compound (27) was deposited at a ratio of 1: 100 was provided as the light emitting layer. The device produced blue-green light emission with a DC voltage of 5 V of 1000 (cd / m 2 ), maximum luminance of 18000 (cd / m 2 ), and luminous efficiency of 1.50 (lm / W).
[0060]
Compound (27)
[0061]
[Formula 4]
In the organic EL device shown in this example, light emission with a maximum light emission luminance of 10,000 (cd / m 2 ) or more was obtained in a two-layer or higher device structure, and high light emission efficiency could be obtained. When the organic EL device shown in this example was continuously emitted at 3 (mA / cm 2 ), stable emission could be observed for 1000 hours or more.
The organic EL device of the present invention achieves improvement in light emission efficiency, light emission luminance and long life, and is used together with light emitting materials, doping materials, hole injection materials, electron injection materials, sensitizers, resins. The electrode material and the element manufacturing method are not limited.
[0064]
【The invention's effect】
The organic EL device using the light emitting material for organic EL of the present invention as a light emitting material showed high luminance and higher luminance than conventional ones, and a long-life organic EL device could be obtained.
Claims (4)
一般式［１］
一般式［２］
General formula [1]
General formula [2]
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| KR100957288B1 (en) | 2002-03-15 | 2010-05-12 | 이데미쓰 고산 가부시키가이샤 | Material for organic electroluminescent devices and organic electroluminescent devices made by using the same |
| JP4316387B2 (en) * | 2002-03-22 | 2009-08-19 | 出光興産株式会社 | Material for organic electroluminescence device and organic electroluminescence device using the same |
| MY145368A (en) * | 2004-01-13 | 2012-01-31 | Nissan Chemical Ind Ltd | Aminoquinoxaline compounds and polyaminoquinoxaline compounds, and use thereof |
| WO2005076295A1 (en) | 2004-02-06 | 2005-08-18 | Yamaguchi University | Electrode for energy storage device and process for producing the same |
| KR20070026544A (en) * | 2004-05-28 | 2007-03-08 | 이데미쓰 고산 가부시키가이샤 | Amine compound and organic electroluminescent element employing the same |
| KR101540037B1 (en) * | 2005-09-12 | 2015-07-29 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | Quinoxaline derivative, and light emitting element, light emitting device, and electronic appliance using the same |
| EP1956011A1 (en) | 2005-11-28 | 2008-08-13 | Idemitsu Kosan Co., Ltd. | Amine compound and organic electroluminescent element employing the same |
| US9287512B2 (en) | 2011-03-08 | 2016-03-15 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compounds, layers and organic electroluminescent device using the same |
| CN106967060B (en) * | 2017-03-28 | 2020-09-11 | 石家庄诚志永华显示材料有限公司 | Series of carbazole derivatives and application thereof |
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