JP7286210B2 - 窒素含有化合物、電子素子及び電子装置 - Google Patents
窒素含有化合物、電子素子及び電子装置 Download PDFInfo
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07C211/56—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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- C07C211/58—Naphthylamines; N-substituted derivatives thereof
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- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
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- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
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Description
R3、R4は、それぞれ独立的に、重水素、ハロゲン、シアノ、炭素数3~20のヘテロアリール、炭素数6~20のアリール、炭素数3~12のトリアルキルシリル、炭素数8~12のアリールシリル、炭素数1~10のアルキル、炭素数1~10のハロアルキル、炭素数2~6のアルケニル、炭素数2~6のアルキニル、炭素数3~20のシクロアルキル、炭素数2~10のヘテロシクロアルキル、炭素数5~10のシクロアルケニル、炭素数4~10のヘテロシクロアルケニル、炭素数1~10のアルコキシ、炭素数1~10のアルキルチオ、炭素数6~18のアリールオキシ、炭素数6~18のアリールチオ、炭素数6~18のホスフィニルオキシ(phosphinyloxy)から選択され、
aが0、1、2、3又は4から選択され、aが2以上の場合、いずれか2つのR3は同じであるか又は異なり、
bが0、1、2又は3から選択され、bが2以上の場合、いずれか2つのR4は同じであるか又は異なり、
Lは、単結合、置換又は非置換の炭素数6~30のアリーレン、置換又は非置換の炭素数3~30のヘテロアリーレンから選択され、
Ar1及びAr2は、それぞれ独立的に、置換又は非置換の、炭素数1~20のアルキル、炭素数3~20のシクロアルキル、炭素数6~30のアリール、炭素数3~30のヘテロアリールから選択され、かつ前記Ar1及びAr2は、いずれも、9,9-ジフェニルフルオレニルではない。
R3、R4は、それぞれ独立的に、重水素、ハロゲン、シアノ、炭素数3~20のヘテロアリール、炭素数6~20のアリール、炭素数3~12のトリアルキルシリル、炭素数8~12のアリールシリル、炭素数1~10のアルキル、炭素数1~10のハロアルキル、炭素数2~6のアルケニル、炭素数2~6のアルキニル、炭素数3~20のシクロアルキル、炭素数2~10のヘテロシクロアルキル、炭素数5~10のシクロアルケニル、炭素数4~10のヘテロシクロアルケニル、炭素数1~10のアルコキシ、炭素数1~10のアルキルチオ、炭素数6~18のアリールオキシ、炭素数6~18のアリールチオ、炭素数6~18のホスフィニルオキシから選択され、
aが0、1、2、3又は4から選択され、aが2以上の場合、いずれか2つのR3は同じであるか又は異なり、bが0、1、2又は3から選択され、bが2以上の場合、いずれか2つのR4は同じであるか又は異なり、
Lは、単結合、置換又は非置換の炭素数6~30のアリーレン、置換又は非置換の炭素数3~30のヘテロアリーレンから選択され、
Ar1及びAr2は、それぞれ独立的に、置換又は非置換の、炭素数1~20のアルキル、炭素数3~20のシクロアルキル、炭素数6~30のアリール、炭素数3~30のヘテロアリールから選択され、かつ前記Ar1及びAr2は、いずれも、9,9-ジフェニルフルオレニルではない。任意選択的には、前記Ar1及びAr2は、両方ともスピロビフルオレニルではない。
Xは、置換又は非置換の炭素数1~10のアルキレン、置換又は非置換の炭素数3~10のシクロアルキレン、置換又は非置換の炭素数6~20のアリーレン、置換又は非置換の炭素数3~20のヘテロアリーレンから選択され、X1~X10は、それぞれ独立的に、C又はNを示し、かつ少なくとも1つはNであり、X11~X15は、それぞれ独立的に、C又はNを示し、かつ少なくとも1つはNであり、X16~X23は、それぞれ独立的に、C又はNを示し、かつ少なくとも1つはNであり、X24、X25は、それぞれ独立的に、単結合、C(R5R6)、N(R7)、O、S、Si(R5R6)、Seから選択され、好ましくは、X24及びX25は、同時に単結合であってはならない。
X26、X27は、それぞれ独立的に、C又はNを示し、かつ少なくとも1つはNであり、
n1、n3、n4、n6、n7、n8、n9、n16、n18、n21は、それぞれ独立的に、1、2、3又は4から選択され、n10、n11、n22は、それぞれ独立的に、1、2又は3から選択され、n13、n20は、1、2、3、4又は5から選択され、n2、n14、n19は、それぞれ独立的に、1、2、3、4、5又は6から選択され、n15は、1、2、3、4、5、6又は7から選択され、n5、n12、n17は、それぞれ独立的に、1、2、3、4、5、6、7又は8から選択される。
Wは、置換又は非置換の炭素数1~10のアルキレン、置換又は非置換の炭素数3~10のシクロアルキレン、置換又は非置換の炭素数6~20のアリーレン、置換又は非置換の炭素数3~20のヘテロアリーレンから選択され、W1、W2は、それぞれ独立的に、C又はNを示し、かつ少なくとも1つはNであり、W3~W7は、それぞれ独立的に、C又はNを示し、かつ少なくとも1つはNであり、W8~W15は、それぞれ独立的に、C又はNを示し、かつ少なくとも1つはNであり、W16、W17は、それぞれ独立的に、単結合、C(R9R10)、N(R8)、O、S、Si(R9R10)、Seから選択され、好ましくは、W16、W17は同時に単結合ではならない。
R8は、水素、重水素、置換又は非置換の炭素数1~6のアルキル、置換又は非置換の炭素数6~20のアリール、置換又は非置換の炭素数3~20のヘテロアリールから選択され、
e1、e11、e14、e15、e17は、それぞれ独立的に、1、2、3、4又は5から選択され、e16、e20は、それぞれ独立的に、1、2又は3から選択され、e2、e9は、それぞれ独立的に、1、2、3、4、5、6又は7から選択され、e3、e4、e5は、それぞれ独立的に、1、2、3、4、5、6、7、8又は9から選択され、e6は、1、2、3、4、5、6、7又は8から選択され、e7、e10、e12、e13、e18、e19は、それぞれ独立的に、1、2、3又は4から選択され、e8は、1、2、3、4、5又は6から選択される。
1HNMR(400MHz, CD2Cl2):8.11 (d,1H), 8.03(d,1H), 7.41-7.63(m,2H), 7.37-7.39(m,1H), 7.30-7.33(m,1H), 7.23-7.24(m,1H), 2.88-2.93(m,2H), 2.81-2.85(m,2H), 2.19(s,2H), 1.99(s,2H), 1.77-1.83(m,4H), 1.54(s,2H).
1H NMR (400MHz, CD2Cl2): 8.11 (d, 1H), 8.02 (d, 1H), 7.64-7.60 (m, 6H), 7.55 (d, 4H), 7.43 (t, 4H), 7.33-7.24 (m, 8H), 7.06 (dd, 1H), 2.91 (m, 4H), 2.19 (m, 2H), 2.00 (s, 2H), 1.82 (d, 4H), 1.61 (s, 2H)。
実施例1
以下の方法で緑色の有機エレクトロルミネッセンスデバイスを製造した。
ITO厚さが1500オングストロームのITO基板(コーニング製)を40mm(長さ)×40mm(幅)×0.7mm(厚さ)の寸法に切断し、フォトリソグラフィ工程を用いて、陰極、陽極及び絶縁層パターンを有する実験基板に製造し、陽極(実験基板)の仕事関数を増加させつつ、スカムを除去するために、紫外線オゾン及びO2:N2プラズマを用いて表面処理を行った。
化合物1の代わりに、以下の表8で合成された化合物をそれぞれ用い、350オングストロームの厚さの第2の正孔輸送層を形成し、対応する緑色の有機エレクトロルミネッセンスデバイスを製造した。
比較例1~比較例7では、化合物1の代わりに、化合物A、化合物B、化合物C、化合物D、化合物E、化合物F、化合物Gをそれぞれ用い、同じ方法に従って、対応する緑色の有機エレクトロルミネッセンスデバイスを製造した。化合物A~化合物Gの構造は、以下のとおりであった。
Claims (8)
- 構造が化学式1で示されることを特徴とする窒素含有化合物。
R1及びR2は、それぞれ独立的に、水素、化学式1-1で示される基から選択され、R1及びR2のうちの1つのみは、化学式1-1で示される基であり、R1又はR2が水素から選択される場合、水素から選択される前記R1又はR2は、R4により置換されることができ、
R3、R4は、それぞれ独立的に、重水素、ハロゲン、シアノ、炭素数3~20のヘテロアリール、炭素数6~20のアリール、炭素数3~12のトリアルキルシリル、炭素数8~12のアリールシリル、炭素数1~10のアルキル、炭素数1~10のハロアルキル、炭素数2~6のアルケニル、炭素数2~6のアルキニル、炭素数3~20のシクロアルキル、炭素数2~10のヘテロシクロアルキル、炭素数5~10のシクロアルケニル、炭素数4~10のヘテロシクロアルケニル、炭素数1~10のアルコキシ、炭素数1~10のアルキルチオ、炭素数6~18のアリールオキシ、炭素数6~18のアリールチオ、炭素数6~18のホスフィニルオキシから選択され、
aが0、1、2、3又は4から選択され、aが2以上の場合、いずれか2つのR3は同じであるか又は異なり、
bが0、1、2又は3から選択され、bが2以上の場合、いずれか2つのR4は同じであるか又は異なり、
Lは、単結合又は以下の基からなる群から選択され、
Ar1及びAr2は、それぞれ独立的に、以下の基からなる群から選択される。
- 前記R3、R4は、それぞれ独立的に、重水素、フッ素、シアノ、炭素数6~18のアリール、炭素数5~18のヘテロアリール、炭素数1~6のアルキル、炭素数3~10のシクロアルキルから選択される、ことを特徴とする請求項1に記載の窒素含有化合物。
- 対向して設けられる陽極と、陰極と、請求項1~3のいずれかに記載の窒素含有化合物を含み、前記陽極と前記陰極との間に設けられる機能層とを含む、ことを特徴とする電子素子。
- 前記機能層は、電子バリア層を含み、前記電子バリア層は前記窒素含有化合物を含む、ことを特徴とする請求項4に記載の電子素子。
- 前記電子素子は、有機エレクトロルミネッセンスデバイス又は光電変換デバイスである、ことを特徴とする請求項4又は5に記載の電子素子。
- 前記有機エレクトロルミネッセンスデバイスは、緑色光デバイスである、ことを特徴とする請求項6に記載の電子素子。
- 請求項4~7のいずれかに記載の電子素子を含む、ことを特徴とする電子装置。
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KR102654237B1 (ko) | 2017-09-25 | 2024-04-03 | 머티어리얼사이언스 주식회사 | 유기 화합물 및 이를 포함하는 유기전계발광 소자 |
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WO2020050623A1 (ko) * | 2018-09-04 | 2020-03-12 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기발광 소자 |
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WO2020080849A1 (ko) * | 2018-10-17 | 2020-04-23 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
KR102225908B1 (ko) * | 2018-10-18 | 2021-03-10 | 주식회사 엘지화학 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
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