CN107936014A - 有机发光材料4,6‑二苯基双茚并蒽唑啉的合成方法及应用 - Google Patents

有机发光材料4,6‑二苯基双茚并蒽唑啉的合成方法及应用 Download PDF

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CN107936014A
CN107936014A CN201711357976.4A CN201711357976A CN107936014A CN 107936014 A CN107936014 A CN 107936014A CN 201711357976 A CN201711357976 A CN 201711357976A CN 107936014 A CN107936014 A CN 107936014A
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diphenyl
double
oxazolines
synthetic method
indeno anthracene
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武亚明
朱红军
章勤
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Nanjing Polytechnic Institute
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Nanjing Polytechnic Institute
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
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    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom

Abstract

本发明提供一种发光材料4,6‑二苯基双茚并蒽唑啉化合物的制备方法及应用。本发明以4,6‑二苯甲酰基‑1,3‑苯二胺和茚酮为原料，利用多聚磷酸为催化剂，以间甲酚为溶剂进行Friedlander缩合反应得到4,6‑二苯基双茚并蒽唑啉。该化合物可作为有机发光二极管的发光层或电子传输层。

Description

有机发光材料4,6-二苯基双茚并蒽唑啉的合成方法及应用
技术领域
本发明属于光电材料技术领域。具体涉及一种4,6-二苯基双茚并蒽唑啉类化合物的合成方法。
背景技术
近年来，有机电致发光二极管(Organic Light-emitting Diode, OLED)的研究和应用取得了长足的进展，已经成为当今显示器件研究中的热门，引起人们的广泛兴趣。这主要由于OLED很好地克服了传统显示器件存在的缺点，具有高亮度﹑宽视角﹑响应速度快﹑全彩色﹑超薄﹑超轻﹑低功耗﹑驱动电压低﹑工艺简单﹑成本低等许多优点，被誉为是新一代平板显示技术的最有力竞争者。
发光材料按照分子结构可以分为：有机小分子材料﹑金属配合物材料和聚合物材料三类。种类最多的一类电致发光材料是有机小分子发光材料，它们一般具有共轭杂环，具有选择范围广、化学修饰性好、易于提纯、耐久性好、荧光量子效率高等优点，包括蒽、芴、苝、芳香胺、卟啉、香豆素、喹吖啶酮、噁二唑、噻唑、喹啉和蒽唑啉等类的衍生物等。
南京工业大学朱红军教授研究小组报道了如下所示的9 个蒽啉类小分子化合物及其相关的光物理化学的研究。
蒽啉类小分子及其聚合物具有优秀的热稳定性，满足了电子器件对耐热性能的基本要求，同时蒽啉主体结构具有较大的π-电子共轭体系，导致该类分子结构中的电子可以发生较大程度的离域，具有较低的禁带宽度(Eg) ，是一种较为理想的电子传输材料。这些基本性质为进一步设计、合成蒽啉类化合物，同时研究该类化合物的性质和应用提供了依据。本次设计合成一个新化合物4,6-二苯基双茚并蒽唑啉，并对其紫外吸收光谱和荧光发射光谱进行研究。
发明内容
本发明的目的在于提出一个具有优良的电子传输能力和发光性能的化合物4,6-二苯基双茚并蒽唑啉的合成方法，以及其作为有机发光二极管的发光层或电子传输层的应用。
本发明中，用1 倍量(物质的量为单位，下同)的4,6-二苯甲酰基-1,3-苯二胺和1: 2.0 至1 : 2.4 倍量的茚酮化合物，采用多聚磷酸催化剂，以间甲酚为溶剂，在100℃至170℃的条件下进行Friedlander 缩合反应10-150小时，得到化合物4,6-二苯基双茚并蒽唑啉，同时得到较为满意的收率(最佳条件时，收率80% 以上) ，反应式为:
4,6-二苯基双茚并蒽唑啉的紫外最大吸收波长位于404nm，最大荧光发射光谱位于459nm，半峰宽约为55 nm，是一类理想的蓝光有机发光材料。
附图说明
图1甲苯溶液中的紫外可见吸收光谱(c=5.0×10-5mol L-1)。
图2甲苯溶液中的荧光发射光谱(c=5.0×10-8mol L-1)。
具体实施方式
实施例1：4,6-二苯基双茚并蒽唑啉的合成
4,6-二苯甲酰基-1,3-苯二胺(0.6328 g, 2.0 mmol)，茚酮(0.53 g, 4.0 mmol)加入到多聚磷酸(4.2g) 和间甲酚(10mL) 混合溶液中，磁力搅拌，控温130-140℃，反应50h。然后冷却至80℃，用甲醇(50mL) 稀释，倒入1mol • L-1 的KOH 水溶液(500mL) 中，过滤，收集沉淀，再用热水洗涤3次(每次500mL)，干燥。最后用甲醇/THF 溶液(甲醇/THF体积比为30-60 % )进行重结晶2 次，得到橙黄色片状固体4,6-二苯基双茚并蒽唑啉0.92g ，收率96% ，紫外吸收光谱见附图1，荧光发射光谱见附图2。
虽然己经用优选实施例详述了本发明，然而其并非用于限定本发明。任何本领域的技术人员，在不脱离本发明的精神和范围的情况下，应当可以作出各种修改与变更。因此本发明的保护范围应当视为所附的权利要求书所限定的范围。

Claims (5)

1.一种4,6-二苯基双茚并蒽唑啉化合物，其特征在于结构式I如下:
一种如权利要求1 所述的4,6-二苯基双茚并蒽唑啉的合成方法，其特征在于：用1 倍量(物质的量为单位，下同)的4,6-二苯甲酰基-1,3-苯二胺和1 : 2.0 至1 : 2.4 倍量的茚酮化合物，采用多聚磷酸催化剂，以间甲酚为溶剂，在100℃至170℃的条件下进行Friedlander 缩合反应10-150小时，得到化合物4,6-二苯基双茚并蒽唑啉。
2.一种如权利要求2 的合成方法，其特征在于4,6-二苯甲酰基-1,3-苯二胺和茚酮物质的量比为1 : 2.0 至1 : 3.0。
3.一种如权利要求2 的合成方法，其特征在于多聚磷酸催化剂与间甲酚质量比例为1:1至1：6。
4.一种如权利要求2 的合成方法，其特征在于反应时间为10至150小时。
5.一种如权利要求1所述的4,6-二苯基双茚并蒽唑啉的应用，可用于有机发光二极管的发光层或电子传输层。
CN201711357976.4A 2017-12-17 2017-12-17 有机发光材料4,6‑二苯基双茚并蒽唑啉的合成方法及应用 Pending CN107936014A (zh)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101337961A (zh) * 2008-07-24 2009-01-07 南京工业大学 有机发光材料蒽啉化合物、合成方法及应用
WO2010114262A2 (en) * 2009-03-31 2010-10-07 Dow Advanced Display Materials,Ltd. Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN101874021A (zh) * 2007-11-30 2010-10-27 出光兴产株式会社 氮杂茚并芴二酮衍生物、有机电致发光元件用材料和有机电致发光元件
CN102443001A (zh) * 2010-10-09 2012-05-09 南京工业大学 有机发光材料4,6-二苯基-1,9-蒽啉类化合物、合成方法及应用

Patent Citations (4)

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Publication number Priority date Publication date Assignee Title
CN101874021A (zh) * 2007-11-30 2010-10-27 出光兴产株式会社 氮杂茚并芴二酮衍生物、有机电致发光元件用材料和有机电致发光元件
CN101337961A (zh) * 2008-07-24 2009-01-07 南京工业大学 有机发光材料蒽啉化合物、合成方法及应用
WO2010114262A2 (en) * 2009-03-31 2010-10-07 Dow Advanced Display Materials,Ltd. Novel organic electroluminescent compounds and organic electroluminescent device using the same
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Application publication date: 20180420