CN103483382A - 一种三芳胺基三苯基膦功能材料及其制备方法 - Google Patents
一种三芳胺基三苯基膦功能材料及其制备方法 Download PDFInfo
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Abstract
本发明属于功能材料领域,具体涉及一种三芳胺基三苯基膦功能材料及其制备方法。本发明提出的功能材料在结构上含有三苯基膦以及取代三芳胺基,其优点如下:(1)由于P元素的存在,分子结构中有多余的孤对电子,属于本征型半导体。(2)P元素的原子半径大,空间位阻小,能构筑更稳定的半导体材料。该材料由三(4-羟基苯基)膦、苯胺、碘、碘代芳香化合物以及碳酸钾为起始原料,通过两步法制备获得,制备工艺简单。
Description
技术领域
本发明属于功能材料技术领域,具体涉及一种三芳胺基三苯基膦功能材料及其制备方法。
背景技术
有机电荷传输材料是一类当有载流子(电子或空穴)注人时,在电场作用下可以实现载流子的定向有序的可控迁移从而达到传输电荷的有机半导体材料,包括空穴传输(p型)和电子传输(n型)两类。有机空穴传输材料目前主要有聚对苯撑乙烯(PPV)类、聚噻吩类、聚硅烷类、三苯甲烷类、三芳胺类、腙类、吡唑啉类、咔唑类、丁二烯类等。其中,三芳胺类材料具有较好的给电子性、较低的离子化电位、较高的空穴迁移、较好的溶解性与无定形成膜性、较强的荧光性能与光稳定性,成为研究的热点,广泛作为空穴传输材料应用于光导体、有机电致发光二极管(OLED)、有机太阳能电池、光折射全息摄像、场效应管等诸多领域。
本发明以P元素为核心,与三个芳香胺连接,形成三苯基膦枝状化合物,是一种新型半导体功能材料,其优点如下:(1)由于P元素的存在,分子结构中有多余的孤对电子,属于本征型半导体。(2)P元素与N元素属同一族,性质相像,但P元素的原子半径更大,空间位阻小,能构筑更稳定的半导体材料。
发明内容
本发明的目的在于提出一类三芳胺基三苯基膦功能材料及其制备方法。
本发明提出的三芳胺基三苯基膦功能材料,在结构上含有三苯基膦,以及取代三芳胺基,其结构式如下所示:
其中R为苯基、4-甲基苯基、4-联苯基、1-萘基之一种。
本发明特别提出以下几种功能材料:
(1)中文名称:三(4-(N,N-二苯胺基)苯基膦
英文名称:4,4',4''-phosphinetriyltris(N,N-diphenylaniline)
分子式为C54H42N3P,化学结构式如下:
(A)
(2)中文名称:三(4-(N-苯基-N-(4-甲基苯基)胺基)苯基膦
英文名称:4,4',4''-phosphinetriyltris(N-phenyl-N-p-tolylaniline)
分子式为C57H48N3P,化学结构式如下:
(B)
(3)中文名称:三(4-(N-苯基-N-(4-联苯基)胺基)苯基膦
英文名称:N,N',N''-(4,4',4''-phosphinetriyltris(benzene-4,1-diyl))tris(N-phenylbiphenyl-4-amine)分子式为C72H54N3P,化学结构式如下:
(C)
(4)中文名称:三(4-(N-苯基-N-(1-萘基)胺基)苯基膦
英文名称:N,N',N''-(4,4',4''-phosphinetriyltris(benzene-4,1-diyl))tris(N-phenylnaphthalen-1-amine)
分子式为C66H48N3P,化学结构式如下:
(D)
本发明还提出了该类功能材料的制备方法,该材料由三(4-羟基苯基)膦、苯胺、碘、碘代芳香化合物以及碳酸钾为起始原料,通过两步法制备获得,反应方程式如下:
具体步骤如下:
氮气保护下,将三(4-羟基苯基)膦与苯胺混合,加入碘,加热至120℃,反应6小时,加入乙醇,过滤,所得固体与碘代芳香化合物、碳酸钾以及正十二烷混合,加入还原铜粉,加热至180℃反应12小时,冷却,加入乙醇,过滤,固体用真空升华法纯化,得目标功能材料。
附图说明
图1为三芳胺基三苯基膦功能材料结构式。
具体实施方式
下面通过实施例进一步描述本发明
实施例1
氮气保护下,在三颈瓶中,将0.01mol三(4-羟基苯基)膦与0.04mol苯胺混合,加入50mg碘,加热至120℃,反应6小时,加入乙醇,过滤,所得固体与0.04mol碘苯、0.02mol碳酸钾以及100mL正十二烷在三颈瓶中混合,加入还原铜粉0.2g,加热至180℃反应12小时,冷却,加入乙醇,过滤,固体用真空升华法纯化,得功能材料三(4-(N,N-二苯胺基)苯基膦(A),收率:66%,熔点:〉300℃,元素分析:C,84.94;H,5.50;N,5.53;P,4.03,计算值C,84.90;H,5.54;N,5.50;P,4.05,质谱测试:m/z:763(100.0%)。
实施例2
氮气保护下,在三颈瓶中,将0.01mol三(4-羟基苯基)膦与0.04mol苯胺混合,加入50mg碘,加热至120℃,反应6小时,加入乙醇,过滤,所得固体与0.04mol4-甲基碘苯、0.02mol碳酸钾以及100mL正十二烷在三颈瓶中混合,加入还原铜粉0.2g,加热至180℃反应12小时,冷却,加入乙醇,过滤,固体用真空升华法纯化,得功能材料三(4-(N-苯基-N-(4-甲基苯基)胺基)苯基膦(B),收率:63%,熔点:〉300℃,元素分析:C,84.90;H,6.04;N,5.24;P,3.82,计算值C,84.94;H,6.00;N,5.21;P,3.84,质谱测试:m/z:805(100.0%)。
实施例3
氮气保护下,在三颈瓶中,将0.01mol三(4-羟基苯基)膦与0.04mol苯胺混合,加入50mg碘,加热至120℃,反应6小时,加入乙醇,过滤,所得固体与0.04mol4-碘联苯、0.02mol碳酸钾以及100mL正十二烷在三颈瓶中混合,加入还原铜粉0.2g,加热至180℃反应12小时,冷却,加入乙醇,过滤,固体用真空升华法纯化,得功能材料三(4-(N-苯基-N-(4-联苯基)胺基)苯基膦(C),收率:73%,熔点:〉300℃,元素分析:C,87.12;H,5.48;N,4.26;P,3.14,计算值C,87.16;H,5.49;N,4.24;P,3.12,质谱测试:m/z:991(100.0%)。
实施例4
氮气保护下,在三颈瓶中,将0.01mol三(4-羟基苯基)膦与0.04mol苯胺混合,加入50mg碘,加热至120℃,反应6小时,加入乙醇,过滤,所得固体与0.04mol1-碘代萘、0.02mol碳酸钾以及100mL正十二烷在三颈瓶中混合,加入还原铜粉0.2g,加热至180℃反应12小时,冷却,加入乙醇,过滤,固体用真空升华法纯化,得功能材料三(4-(N-苯基-N-(1-萘基)胺基)苯基膦(D),收率:39%,熔点:〉300℃,元素分析C,86.70;H,5.28;N,4.64;P,3.38,计算值C,86.72;H,5.29;N,4.60;P,3.39,质谱测试:m/z:913(100.0%)。
Claims (6)
1.一种三芳胺基三苯基膦功能材料及其制备方法,其特征在于该材料在结构上含有三苯基膦,以及取代三芳胺基,其结构式如下所示:
其中R为苯基、4-甲基苯基、4-联苯基、1-萘基之一种。
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JP2003317965A (ja) * | 2002-04-25 | 2003-11-07 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子および表示装置 |
US20040002605A1 (en) * | 2002-06-27 | 2004-01-01 | Lelia Cosimbescu | Synthesis for quinacridone compounds |
CN102046871A (zh) * | 2008-06-02 | 2011-05-04 | 3M创新有限公司 | 包含电荷加强添加剂的驻极体料片 |
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JP2003317965A (ja) * | 2002-04-25 | 2003-11-07 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子および表示装置 |
US20040002605A1 (en) * | 2002-06-27 | 2004-01-01 | Lelia Cosimbescu | Synthesis for quinacridone compounds |
CN102046871A (zh) * | 2008-06-02 | 2011-05-04 | 3M创新有限公司 | 包含电荷加强添加剂的驻极体料片 |
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YASUHIKO SHIROTA,ET AL.: "Organic materials for electronic and optoelectronic devices", 《J. MATER. CHEM.》 * |
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