JP5638960B2 - 有機エレクトロルミネセントデバイスのための新規材料 - Google Patents
有機エレクトロルミネセントデバイスのための新規材料 Download PDFInfo
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- JP5638960B2 JP5638960B2 JP2010546263A JP2010546263A JP5638960B2 JP 5638960 B2 JP5638960 B2 JP 5638960B2 JP 2010546263 A JP2010546263 A JP 2010546263A JP 2010546263 A JP2010546263 A JP 2010546263A JP 5638960 B2 JP5638960 B2 JP 5638960B2
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- UEWHMHUEUVHQQH-UHFFFAOYSA-N OC(c1cc2ccccc2c2cc(Br)ccc12)=O Chemical compound OC(c1cc2ccccc2c2cc(Br)ccc12)=O UEWHMHUEUVHQQH-UHFFFAOYSA-N 0.000 description 1
- OULPKDZSDWWWTD-UHFFFAOYSA-N c(cc1)ccc1-[n]1c(-c(cc2)ccc2-c2c(cccc3)c3c(-c3cc(c4ccccc4cc4)c4cc3)c3c2cccc3)nc2c1cccc2 Chemical compound c(cc1)ccc1-[n]1c(-c(cc2)ccc2-c2c(cccc3)c3c(-c3cc(c4ccccc4cc4)c4cc3)c3c2cccc3)nc2c1cccc2 OULPKDZSDWWWTD-UHFFFAOYSA-N 0.000 description 1
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Description
Arは、H、Dまたは、5〜60の芳香環原子を有する芳香族または芳香族複素環系であり、これは一以上の非芳香族基R1によって置換されてよく;
R1は、各々の存在について同じまたは異なり、H、D、F、Cl、Br、I、CHO、N(Ar1)2、C(=O)Ar1、P(Ar1)2、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、CR3=CR3Ar1、CN、NO2、Si(R3)3、B(OAr1)2、B(OR3)2、OSO2R3、OH、1〜40のC原子を有する直鎖アルキル、アルコキシ、もしくはチオアルコキシ基、または3〜40のC原子を有する分枝または環状のアルキル、アルコキシもしくはチオアルコキシ基であり、それぞれ一以上の基R3によって置換されてよく、一以上の非隣接CH2基がR3C=CR3、C≡C、Si(R3)2、Ge(R3)2、Sn(R3)2、C=O、C=S、C=Se、C=NR3、P(=O)(R3)、SO、SO2、NR3、O、SまたはCONR3によって置換されてよく、一以上のH原子がF、Cl、Br、I、CNまたはNO2、または5〜60の芳香環原子を有する芳香族もしくは芳香族複素環系によって置換されてよく、これは一以上の非芳香族基R1によって置換されてよく、またはこれらの系の組合せであり;
R2は、各々の存在について同じまたは異なり、R1であるか、または2以上の隣接する置換基R2が互いに単環または多環の脂肪族もしくは芳香族環系を形成し;
Ar1は、各々の存在について同じまたは異なり、5〜30の芳香環原子を有する芳香族または芳香族複素環系であって、これは一以上の非芳香族基R3によって置換されてよく;同じ窒素またはリン原子に結合する2つの基Ar1は、ここで単結合またはB(R3)、C(R3)2、Si(R3)2、C=O、C=NR3、C=C(R3)2、O、S、S=O、SO2、N(R3)、P(R3)、およびP(=O)R3から選択される架橋により互いに結合し;
R3は、各々の存在について同じまたは異なり、Hまたは1〜20のC原子を有する脂肪族、芳香族および/または芳香族複素環炭化水素基であり、その中でさらに一以上のH原子はFによって置換されてよく;ここで2以上の隣接する置換基R3が互いに、単環または多環の脂肪族もしくは芳香族環系を形成し;
以下の2つの化合物は本発明から除かれる:
Ar2は、5〜16の芳香環原子を有するアリールまたはヘテロアリール基であり、好ましくはフェニル、1−ナフチル、2−ナフチル、9−アントリル、クリセニル、1−ピレニル、2−ピレニル、2−フェナントレニル、3−フェナントレニル、9−フェナントレニル、2−ベンズイミダゾール、またはフルオロアンテニルであり、それぞれ一以上の基R1によって置換されてよい;
qは、0、1、2または3であり、好ましくは1または2であり、特に好ましくは1である。
蒸着される。
以下の合成は他に示さない限り、保護的ガス環境下、乾燥溶媒中で行われる。出発物質は、ALDRICHから購入してよい。
WO 04/058911において一般的に記載され、且つ、各々の場合においてそれぞれの状況に適合する方法によってOLEDを製造する(例えば、最適な効率または色を達成するための種々の層厚)。
Claims (11)
- 式(1):
Arは、ベンゼン、ナフタレン、アントラセン、カルバゾール、フェナントレン、ベンズアントラセン、クリセン、ピレン、フェナントロリン、トリアジン、およびベンズイミダゾールから構築される5〜30の芳香環原子を有する芳香族または芳香族複素環系で
あり、これは一以上の非芳香族基R1によって置換されてよく;
R1およびR2は、各々の存在について同じまたは異なり、H、F、N(Ar1)2、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、CR3=CR3Ar1、Si(R3)3、B(OAr1)2、B(OR3)2、1〜10のC原子を有する直鎖アルキル基、または3〜10のC原子を有する分枝もしくは環状アルキル基を意味し、これはそれぞれ一以上の基R3によって置換されてよく、ここで一以上の非隣接CH2基はR3C=CR3、C≡C、NR3またはOによって置換されてよく、一以上のH原子はF、または5〜30の芳香環原子を有する芳香族もしくは芳香族複素環系、これはそれぞれ一以上の非芳香族基R1によって置換されてよく、またはこれらの系の組合せによって置換されてよく;
Ar1は、各々の存在について同じまたは異なり、5〜30の芳香環原子を有する芳香
族または芳香族複素環系であって、これは一以上の非芳香族基R3によって置換されてよく;同じ窒素またはリン原子に結合する2つの基Ar1は、ここで単結合、またはB(R3)、C(R3)2、Si(R3)2、C=O、C=NR3、C=C(R3)2、O、S、S=O、SO2、N(R3)、P(R3)、およびP(=O)R3から選択される架橋により互いに結合し;
R3は、各々の存在について同じまたは異なり、Hまたは1〜20のC原子を有する脂
肪族、芳香族および/または芳香族複素環炭化水素基であり、その中でさらに一以上のH
原子はFによって置換されてよく;ここで2以上の隣接する置換基R3が互いに、単環ま
たは多環の脂肪族もしくは芳香族環系を形成する;
の化合物であって、
以下の2つの化合物:
- 請求項1または2に記載の化合物であって、当該Ar基がフェニル、オルト−、メタ−もしくはパラ−ビフェニル、1−もしくは2−ナフチル、2−、3−もしくは9−フェナントレニル、パラ−フェニレン−1−ナフチル、パラ−フェニレン−2−ナフチル、2−フルオレニル、または2−スピロビフルオレニルから選択され、これはそれぞれ一以上の基R1によって置換されてよく、あるいは、当該Ar基が以下の式(8)、(9)、(10)および(11):
Ar2は、5〜16の芳香環原子を有するアリールまたはヘテロアリール基であり、これはそれぞれ一以上の基R1によって置換されてよく;
qは、0、1、2または3である、
から選択されることを特徴とする化合物。 - 請求項1〜3何れか1項に記載の化合物の製造方法であって、10位で、塩素、臭素、ヨウ素、トリフレート、トシレート、ボロン酸またはボロン酸エステルから選択される反応性遊離基によって置換される9−アリール置換アントラセン、または対応するベンズ[a]アントラセンもしくはテトラセンを、3位で、塩素、臭素、ヨウ素、トリフレート、トシレート、ボロン酸またはボロン酸エステルによって官能基化されるフェナントレン誘導体とカップリングし、ここでフェナントレンおよび同様にアントラセン、ベンズアントラセン、またはテトラセンは一以上の置換基R1によって置換されてもよいことを特徴とする製造方法。
- 請求項1〜3何れか1項に記載の化合物の電子デバイスにおける使用。
- 請求項1〜3何れか1項に記載の少なくとも一つの化合物を含むことを特徴とする電子デバイス。
- 請求項6に記載の電子デバイスであって、有機エレクトロルミネセントデバイス(OLED)、有機電界効果トランジスタ(O−FET)、有機薄膜トランジスタ(O−TFT)、有機発光トランジスタ(O−LET)、有機集積回路(O−IC)、有機太陽電池(O−SC)、有機電界クエンチデバイス(O−FQD)、発光電気化学セル(LEC)、有機レーザーダイオード(O−laser)および有機光受容体からなる群より選択される電子デバイス。
- 発光層または別の層であってよい少なくとも一つの有機層が、請求項1〜3何れか1項に記載の少なくとも一つの化合物を含むことを特徴とする、陽極、陰極および少なくとも一つの発光層を含む有機エレクトロルミネセントデバイス。
- 請求項8に記載の有機エレクトロルミネセントデバイスであって、請求項1〜3何れか1項に記載の化合物が、蛍光ドーパントのホスト材料として使用されることを特徴とする有機エレクトロルミネセントデバイス。
- 請求項8または9に記載の有機エレクトロルミネセントデバイスであって、モノスチリルアミン、ジスチリルアミン、トリスチリルアミン、テトラスチリルアミン、スチリルホスフィン、スチリルエーテル、アリールアミン、インデノフルオレンアミン、またはインデノフルオレンジアミン、ベンゾインデノフルオレンアミン、またはベンゾインデノフルオレンジアミン、またはジベンゾインデノフルオレンアミン、またはジベンゾインデノフルオレンジアミンからなる群より選択される化合物を蛍光ドーパントとして含むことを特徴とする有機エレクトロルミネセントデバイス。
- 請求項8〜10何れか1項に記載の有機エレクトロルミネセントデバイスであって、請求項1〜3何れか1項に記載の化合物が、蛍光またはりん光デバイスにおいて電子輸送材料または正孔阻止材料として使用されることを特徴とする有機エレクトロルミネセントデバイス。
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Families Citing this family (67)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102010048608A1 (de) * | 2010-10-15 | 2012-04-19 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
JP5653179B2 (ja) * | 2010-11-05 | 2015-01-14 | キヤノン株式会社 | フェナンスレン化合物及びこれを用いた有機発光素子 |
KR101432600B1 (ko) | 2010-12-31 | 2014-08-21 | 제일모직주식회사 | 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 |
KR101996648B1 (ko) * | 2011-04-15 | 2019-07-04 | 에스에프씨 주식회사 | 신규한 화합물 및 이를 포함하는 유기전계발광소자 |
KR102168730B1 (ko) | 2012-09-12 | 2020-10-22 | 이데미쓰 고산 가부시키가이샤 | 신규 화합물, 유기 일렉트로 루미네선스 소자용 재료, 유기 일렉트로 루미네선스 소자 및 전자 기기 |
JP6469579B2 (ja) | 2012-10-31 | 2019-02-13 | メルク パテント ゲーエムベーハー | 電子素子 |
KR101716069B1 (ko) | 2012-11-12 | 2017-03-13 | 메르크 파텐트 게엠베하 | 전자 소자용 재료 |
KR102013879B1 (ko) * | 2012-11-30 | 2019-08-29 | 엘지디스플레이 주식회사 | 유기발광장치 및 그 제조방법 |
EP2941470B1 (de) | 2013-01-03 | 2018-09-05 | Merck Patent GmbH | Elektronische vorrichtung |
WO2014106524A2 (de) | 2013-01-03 | 2014-07-10 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
KR20150026114A (ko) | 2013-08-30 | 2015-03-11 | 삼성디스플레이 주식회사 | 인데노피리딘계 화합물 및 이를 포함한 유기 발광 소자 |
CN105636944B (zh) * | 2013-10-14 | 2019-03-01 | 默克专利有限公司 | 用于电子器件的材料 |
CN106132910B (zh) * | 2014-03-07 | 2019-10-11 | 默克专利有限公司 | 电子器件的材料 |
JP6305798B2 (ja) * | 2014-03-17 | 2018-04-04 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子および電子機器 |
WO2016109386A1 (en) | 2014-12-29 | 2016-07-07 | Dow Global Technologies Llc | Compositions with triarylamine derivatives and oled device containing the same |
US20180006237A1 (en) | 2015-01-30 | 2018-01-04 | Merck Patent Gmbh | Materials for electronic devices |
KR102424977B1 (ko) | 2015-04-14 | 2022-07-26 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
KR102471110B1 (ko) | 2015-08-11 | 2022-11-28 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
CN107849444A (zh) * | 2015-08-28 | 2018-03-27 | 默克专利有限公司 | 用于电子器件的化合物 |
KR102606275B1 (ko) | 2015-10-27 | 2023-12-05 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR102630644B1 (ko) | 2015-12-17 | 2024-01-30 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR20180111905A (ko) | 2016-02-05 | 2018-10-11 | 메르크 파텐트 게엠베하 | 전자 소자용 재료 |
KR102603865B1 (ko) | 2016-04-21 | 2023-11-21 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
TWI764942B (zh) | 2016-10-10 | 2022-05-21 | 德商麥克專利有限公司 | 電子裝置 |
DE102017008794A1 (de) | 2016-10-17 | 2018-04-19 | Merck Patent Gmbh | Materialien zur Verwendung in elektronischen Vorrichtungen |
KR20190079646A (ko) | 2016-11-02 | 2019-07-05 | 메르크 파텐트 게엠베하 | 전자 소자용 재료 |
KR102564613B1 (ko) | 2016-11-08 | 2023-08-07 | 메르크 파텐트 게엠베하 | 전자 소자용 화합물 |
TW201833118A (zh) | 2016-11-22 | 2018-09-16 | 德商麥克專利有限公司 | 用於電子裝置之材料 |
TWI761406B (zh) | 2016-12-22 | 2022-04-21 | 德商麥克專利有限公司 | 電子裝置用材料 |
JP7069184B2 (ja) | 2017-02-02 | 2022-05-17 | メルク パテント ゲーエムベーハー | 電子デバイス用材料 |
CN110325524A (zh) | 2017-03-02 | 2019-10-11 | 默克专利有限公司 | 用于有机电子器件的材料 |
US11649249B2 (en) | 2017-04-25 | 2023-05-16 | Merck Patent Gmbh | Compounds for electronic devices |
KR20230117645A (ko) | 2017-04-26 | 2023-08-08 | 오티아이 루미오닉스 인크. | 표면의 코팅을 패턴화하는 방법 및 패턴화된 코팅을포함하는 장치 |
TW201920343A (zh) | 2017-06-21 | 2019-06-01 | 德商麥克專利有限公司 | 電子裝置用材料 |
US11767299B2 (en) | 2017-06-23 | 2023-09-26 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
CN110770363A (zh) | 2017-06-26 | 2020-02-07 | 默克专利有限公司 | 均质混合物 |
TW201920070A (zh) | 2017-06-28 | 2019-06-01 | 德商麥克專利有限公司 | 用於電子裝置之材料 |
TWI779067B (zh) | 2017-07-28 | 2022-10-01 | 德商麥克專利有限公司 | 電子裝置用材料 |
WO2019048443A1 (de) | 2017-09-08 | 2019-03-14 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
EP4242286A3 (de) | 2017-11-23 | 2023-10-04 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
KR20240025066A (ko) | 2017-12-15 | 2024-02-26 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 치환된 방향족 아민 |
KR20200100699A (ko) | 2017-12-20 | 2020-08-26 | 메르크 파텐트 게엠베하 | 헤테로방향족 화합물 |
US11751415B2 (en) | 2018-02-02 | 2023-09-05 | Oti Lumionics Inc. | Materials for forming a nucleation-inhibiting coating and devices incorporating same |
CN108191767A (zh) * | 2018-02-07 | 2018-06-22 | 瑞声科技(南京)有限公司 | Tadf材料及在有机发光二极管器件中的应用 |
KR102230988B1 (ko) * | 2018-03-14 | 2021-03-23 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
EP3765444A1 (en) | 2018-03-16 | 2021-01-20 | Merck Patent GmbH | Materials for organic electroluminescent devices |
EP3598515A1 (en) * | 2018-07-18 | 2020-01-22 | Novaled GmbH | Compound and organic semiconducting layer, organic electronic device, display device and lighting device comprising the same |
CN111349055B (zh) * | 2018-12-24 | 2023-04-21 | 烟台显华光电材料研究院有限公司 | 一类用作电致发光材料的多环化合物及应用 |
US20220127286A1 (en) | 2019-03-04 | 2022-04-28 | Merck Patent Gmbh | Ligands for nano-sized materials |
KR20210149058A (ko) | 2019-03-07 | 2021-12-08 | 오티아이 루미오닉스 인크. | 핵생성 억제 코팅물 형성용 재료 및 이를 포함하는 디바이스 |
CN110041159A (zh) * | 2019-04-24 | 2019-07-23 | 北京诚志永华显示科技有限公司 | 新型化合物、有机电致发光材料、有机电致发光元件、电子装置 |
TW202200529A (zh) | 2020-03-13 | 2022-01-01 | 德商麥克專利有限公司 | 有機電致發光裝置 |
KR20230043106A (ko) | 2020-07-22 | 2023-03-30 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 재료 |
CN115885599A (zh) | 2020-07-22 | 2023-03-31 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
TW202237797A (zh) | 2020-11-30 | 2022-10-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
KR20230116914A (ko) | 2020-12-07 | 2023-08-04 | 오티아이 루미오닉스 인크. | 핵 생성 억제 코팅 및 하부 금속 코팅을 사용한 전도성 증착 층의 패턴화 |
TW202305091A (zh) | 2021-04-09 | 2023-02-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
KR20230169215A (ko) | 2021-04-09 | 2023-12-15 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 재료 |
WO2023052313A1 (de) | 2021-09-28 | 2023-04-06 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2023052275A1 (de) | 2021-09-28 | 2023-04-06 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2023052272A1 (de) | 2021-09-28 | 2023-04-06 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
CN118056486A (zh) | 2021-09-28 | 2024-05-17 | 默克专利有限公司 | 用于电子器件的材料 |
WO2023094412A1 (de) | 2021-11-25 | 2023-06-01 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2023117837A1 (de) | 2021-12-21 | 2023-06-29 | Merck Patent Gmbh | Verfahren zur herstellung von deuterierten organischen verbindungen |
WO2023152346A1 (de) | 2022-02-14 | 2023-08-17 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2023222559A1 (de) | 2022-05-18 | 2023-11-23 | Merck Patent Gmbh | Verfahren zur herstellung von deuterierten organischen verbindungen |
WO2024013004A1 (de) | 2022-07-11 | 2024-01-18 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
Family Cites Families (39)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4539507A (en) | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
US5151629A (en) | 1991-08-01 | 1992-09-29 | Eastman Kodak Company | Blue emitting internal junction organic electroluminescent device (I) |
DE59510315D1 (de) * | 1994-04-07 | 2002-09-19 | Covion Organic Semiconductors | Spiroverbindungen und ihre Verwendung als Elektrolumineszenzmaterialien |
DE19652261A1 (de) | 1996-12-16 | 1998-06-18 | Hoechst Ag | Arylsubstituierte Poly(p-arylenvinylene), Verfahren zur Herstellung und deren Verwendung in Elektroluminszenzbauelementen |
US5935721A (en) | 1998-03-20 | 1999-08-10 | Eastman Kodak Company | Organic electroluminescent elements for stable electroluminescent |
WO2001021729A1 (fr) | 1999-09-21 | 2001-03-29 | Idemitsu Kosan Co., Ltd. | Support organique a electroluminescence et support organique lumineux |
JP4094203B2 (ja) * | 2000-03-30 | 2008-06-04 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子及び有機発光媒体 |
JP2001332384A (ja) | 2000-05-19 | 2001-11-30 | Toray Ind Inc | 発光素子 |
CN1239447C (zh) | 2002-01-15 | 2006-02-01 | 清华大学 | 一种有机电致发光材料 |
JP4170655B2 (ja) | 2002-04-17 | 2008-10-22 | 出光興産株式会社 | 新規芳香族化合物及びそれを利用した有機エレクトロルミネッセンス素子 |
WO2003095445A1 (en) | 2002-05-07 | 2003-11-20 | Lg Chem, Ltd. | New organic compounds for electroluminescence and organic electroluminescent devices using the same |
WO2004018588A1 (ja) | 2002-07-19 | 2004-03-04 | Idemitsu Kosan Co., Ltd. | 有機エレクトロルミネッセンス素子及び有機発光媒体 |
JP4025137B2 (ja) | 2002-08-02 | 2007-12-19 | 出光興産株式会社 | アントラセン誘導体及びそれを利用した有機エレクトロルミネッセンス素子 |
JP2004075567A (ja) | 2002-08-12 | 2004-03-11 | Idemitsu Kosan Co Ltd | オリゴアリーレン誘導体及びそれを利用した有機エレクトロルミネッセンス素子 |
WO2004018587A1 (ja) * | 2002-08-23 | 2004-03-04 | Idemitsu Kosan Co., Ltd. | 有機エレクトロルミネッセンス素子及びアントラセン誘導体 |
KR101030158B1 (ko) | 2002-12-23 | 2011-04-18 | 메르크 파텐트 게엠베하 | 유기 전자발광 부품 |
DE10333232A1 (de) | 2003-07-21 | 2007-10-11 | Merck Patent Gmbh | Organisches Elektrolumineszenzelement |
JP4070676B2 (ja) | 2003-07-25 | 2008-04-02 | 三井化学株式会社 | 非対称置換アントラセン化合物、および該非対称置換アントラセン化合物を含有する有機電界発光素子 |
US7887931B2 (en) * | 2003-10-24 | 2011-02-15 | Global Oled Technology Llc | Electroluminescent device with anthracene derivative host |
TWI373506B (en) | 2004-05-21 | 2012-10-01 | Toray Industries | Light-emitting element material and light-emitting material |
DE102004031000A1 (de) | 2004-06-26 | 2006-01-12 | Covion Organic Semiconductors Gmbh | Organische Elektrolumineszenzvorrichtungen |
TW200613515A (en) * | 2004-06-26 | 2006-05-01 | Merck Patent Gmbh | Compounds for organic electronic devices |
ITRM20040352A1 (it) * | 2004-07-15 | 2004-10-15 | Univ Roma La Sapienza | Derivati oligomerici dello spirobifluorene, loro preparazione e loro uso. |
JP4677221B2 (ja) | 2004-11-26 | 2011-04-27 | キヤノン株式会社 | 有機発光素子 |
TW200639140A (en) | 2004-12-01 | 2006-11-16 | Merck Patent Gmbh | Compounds for organic electronic devices |
DE102005023437A1 (de) | 2005-05-20 | 2006-11-30 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtungen |
US7300511B2 (en) | 2005-07-01 | 2007-11-27 | Sun Chemical Corporation | Low viscosity, highly pigmented oil based dispersions exhibiting a low relative interfacial tension drop |
JP4842587B2 (ja) * | 2005-08-11 | 2011-12-21 | 株式会社半導体エネルギー研究所 | フェナントロリン誘導体化合物、並びにそれを利用する電子輸送性材料、発光素子、発光装置及び電子機器 |
DE102005058543A1 (de) | 2005-12-08 | 2007-06-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
JP2007230951A (ja) | 2006-03-02 | 2007-09-13 | Canon Inc | シリル化合物、発光材料およびそれを用いた有機発光素子 |
DE102006015183A1 (de) | 2006-04-01 | 2007-10-04 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
EP2008992A4 (en) * | 2006-04-18 | 2011-03-09 | Idemitsu Kosan Co | AROMATIC AMINE DERIVATIVE AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME |
JP5317414B2 (ja) * | 2006-04-20 | 2013-10-16 | キヤノン株式会社 | ジベンゾアントラセン化合物およびそれを有する有機発光素子 |
JP2007308477A (ja) | 2006-04-20 | 2007-11-29 | Canon Inc | 化合物および有機発光素子 |
DE102006025846A1 (de) * | 2006-06-02 | 2007-12-06 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102006031990A1 (de) | 2006-07-11 | 2008-01-17 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
KR101321500B1 (ko) * | 2006-09-29 | 2013-10-30 | 삼성디스플레이 주식회사 | 유기 전계 발광 화합물 및 이를 이용한 유기 전계 발광소자 |
US8795855B2 (en) * | 2007-01-30 | 2014-08-05 | Global Oled Technology Llc | OLEDs having high efficiency and excellent lifetime |
WO2009069566A1 (ja) | 2007-11-29 | 2009-06-04 | Idemitsu Kosan Co., Ltd. | ベンゾフェナントレン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
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JP2011514885A (ja) | 2011-05-12 |
US20100327270A1 (en) | 2010-12-30 |
DE102008008953A1 (de) | 2009-08-20 |
WO2009100925A1 (de) | 2009-08-20 |
DE102008008953B4 (de) | 2019-05-09 |
TWI473778B (zh) | 2015-02-21 |
US8993123B2 (en) | 2015-03-31 |
CN101939279A (zh) | 2011-01-05 |
TW200951100A (en) | 2009-12-16 |
CN101939279B (zh) | 2015-03-25 |
KR101573096B1 (ko) | 2015-11-30 |
EP2240425A1 (de) | 2010-10-20 |
KR20100110895A (ko) | 2010-10-13 |
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