JP6208424B2 - フッ素置換されたアリール基を有するアミン誘導体、それを含む有機el材料及びそれを用いた有機el素子 - Google Patents
フッ素置換されたアリール基を有するアミン誘導体、それを含む有機el材料及びそれを用いた有機el素子 Download PDFInfo
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Description
[式(1)中、Ar1及びAr2は、それぞれ独立的に置換もしくは無置換のアリール基又は置換もしくは無置換のヘテロアリール基であり、Lは、置換もしくは無置換のアリーレン基又は置換もしくは無置換のヘテロアリーレン基であり、R1及びR2は、それぞれ独立的に水素原子、置換もしくは無置換のアルキル基、置換もしくは無置換のアルコキシ基、置換もしくは無置換のアリール基、又は置換もしくは無置換のヘテロアリール基であり、aは0≦a≦3を満たす整数であり、Ar1及びAr2のうち少なくとも一方は、少なくとも1つのフッ素原子で置換されている。]
[式(1)中、Ar1及びAr2は、それぞれ独立的に置換もしくは無置換のアリール基又は置換もしくは無置換のヘテロアリール基であり、Lは、置換もしくは無置換のアリーレン基又は置換もしくは無置換のヘテロアリーレン基であり、R1及びR2は、それぞれ独立的に水素原子、置換もしくは無置換のアルキル基、置換もしくは無置換のアルコキシ基、置換もしくは無置換のアリール基、又は置換もしくは無置換のヘテロアリール基であり、aは0≦a≦3を満たす整数であり、Ar1及びAr2のうち少なくとも一方は、少なくとも1つのフッ素原子で置換されている。]
本発明のフッ素置換されたアリール基を有するアミン誘導体を正孔輸送材料に用いた有機EL素子の発光寿命(T50%)を測定した。有機EL素子の正孔輸送材料として、上述の化合物14、16、143及び147を使用した。また、比較化合物として以下の構造式で表せる比較化合物1及び比較化合物2を有機EL素子の正孔輸送材料として使用した。また、ここでは、化合物14を正孔輸送材料に用いた有機EL素子を実施例1、化合物16を正孔輸送材料に用いた有機EL素子を実施例2、化合物143を正孔輸送材料に用いた有機EL素子を実施例3、化合物147を正孔輸送材料に用いた有機EL素子を実施例4、比較化合物1を正孔輸送材料に用いた有機EL素子を比較例1、比較化合物2を正孔輸送材料に用いた有機EL素子を比較例2とする。
102 ガラス基板
104 陽極
106 正孔注入層
108 正孔輸送層
110 発光層
112 電子輸送層
114 電子注入層
116 陰極
Claims (11)
- 下記式(1)
で表されるフッ素置換されたアリール基を有するモノアミン誘導体。 - 下記式(2)又は下記式(3)で表される請求項1に記載のフッ素置換されたアリール基を有するモノアミン誘導体。
- 前記Ar1及びAr2は、それぞれ独立的に炭素数6〜20の置換もしくは無置換のアリール基であり、前記Lは、炭素数6〜20の置換もしくは無置換のアリーレン基であることを特徴とする請求項1又は請求項2に記載のフッ素置換されたアリール基を有するモノアミン誘導体。
- 前記Ar1及びAr2は、それぞれ独立的に置換もしくは無置換のフェニル基又はビフェニル基であり、前記Lは、フェニレン基又はビフェニリレン基であることを特徴とする請求項3に記載のフッ素置換されたアリール基を有するモノアミン誘導体。
- 前記R1及びR2は、それぞれ独立的に水素原子、又は置換もしくは無置換のアリール基であることを特徴とする請求項1乃至請求項4の何れか一項に記載のフッ素置換されたアリール基を有するモノアミン誘導体。
- 前記Ar1及びAr2は、それぞれ独立的に置換もしくは無置換のビフェニル基であり、前記Lは、置換もしくは無置換のフェニレン基であり、前記R1は、水素原子であり、前記R2は、置換もしくは無置換のアリール基であることを特徴とする請求項1又は請求項2に記載のフッ素置換されたアリール基を有するモノアミン誘導体。
- 請求項1乃至請求項6のいずれか一項に記載のフッ素置換されたアリール基を有するモノアミン誘導体を含有する有機EL材料。
- 請求項1乃至請求項6のいずれか一項に記載のフッ素置換されたアリール基を有するモノアミン誘導体を含有する正孔輸送材料。
- 陰極と陽極との間に少なくとも発光層及び正孔輸送層が挟持されている有機EL素子において、該正孔輸送層が、請求項1乃至請求項6のいずれか一項に記載のフッ素置換されたアリール基を有するモノアミン誘導体を成分として含有する有機EL素子。
- 前記R1は、水素原子、無置換のアルキル基、無置換のアルコキシ基、無置換のアリール基、又は無置換のヘテロアリール基であり、前記aは、1≦a≦3を満たす整数であり、前記Lは、無置換のフェニレン基又は無置換のビフェニレン基であり、前記Ar1及びAr2は、それぞれ独立的に置換もしくは無置換のフェニル基又は置換もしくは無置換のビフェニル基であることを特徴とする、請求項1に記載のフッ素置換されたアリール基を有するモノアミン誘導体。
- 前記一般式(1)で表わされる化合物は、以下の構造式により示された物質であることを特徴とする請求項1に記載のフッ素置換されたアリール基を有するモノアミン誘導体。
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JP2012266795A JP6208424B2 (ja) | 2012-12-05 | 2012-12-05 | フッ素置換されたアリール基を有するアミン誘導体、それを含む有機el材料及びそれを用いた有機el素子 |
KR1020130140690A KR102165816B1 (ko) | 2012-12-05 | 2013-11-19 | 아민 유도체, 그것을 포함하는 유기 el 재료 및 그것을 포함하는 유기 el 소자 |
US14/097,686 US9502661B2 (en) | 2012-12-05 | 2013-12-05 | Amine derivative, organic electroluminescence material having the same and organic electroluminescence device using the material |
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JP2012266795A JP6208424B2 (ja) | 2012-12-05 | 2012-12-05 | フッ素置換されたアリール基を有するアミン誘導体、それを含む有機el材料及びそれを用いた有機el素子 |
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JP6208424B2 true JP6208424B2 (ja) | 2017-10-04 |
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TWI615389B (zh) * | 2013-03-01 | 2018-02-21 | 九州有機光材股份有限公司 | 化合物、發光材料及有機發光元件 |
US10651389B2 (en) | 2013-07-02 | 2020-05-12 | Merck Patent Gmbh | Materials for electronic devices |
JP2015122383A (ja) * | 2013-12-20 | 2015-07-02 | 三星ディスプレイ株式會社Samsung Display Co.,Ltd. | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
US10461260B2 (en) * | 2014-06-03 | 2019-10-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102263826B1 (ko) * | 2014-10-06 | 2021-06-11 | 솔루스첨단소재 주식회사 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
WO2016107459A1 (en) * | 2014-12-29 | 2016-07-07 | Dow Global Technologies Llc | Compositions with 2, 3-disubstituted indoles as charge transport materials, and display devices fabricated therefrom |
US11895909B2 (en) | 2015-04-29 | 2024-02-06 | Samsung Display Co., Ltd. | Organic light-emitting device |
KR102602250B1 (ko) * | 2016-02-05 | 2023-11-17 | 삼성디스플레이 주식회사 | 유기 전계 발광 소자용 재료 및 이를 포함하는 유기 전계 발광 소자 |
KR20190067183A (ko) * | 2016-10-13 | 2019-06-14 | 히타치가세이가부시끼가이샤 | 유기 일렉트로닉스 재료, 잉크 조성물 및 유기 일렉트로닉스 소자 |
KR20200099249A (ko) | 2019-02-13 | 2020-08-24 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR20210123896A (ko) * | 2020-04-06 | 2021-10-14 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치 |
KR20220134367A (ko) * | 2021-03-26 | 2022-10-05 | 주식회사 랩토 | 핵생성 억제 형성용 물질 및 이를 포함하는 유기전계발광소자 |
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