CN111592540B - 一种咪唑并萘啶类高性能光电材料及其应用 - Google Patents
一种咪唑并萘啶类高性能光电材料及其应用 Download PDFInfo
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- CN111592540B CN111592540B CN202010537934.4A CN202010537934A CN111592540B CN 111592540 B CN111592540 B CN 111592540B CN 202010537934 A CN202010537934 A CN 202010537934A CN 111592540 B CN111592540 B CN 111592540B
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- C—CHEMISTRY; METALLURGY
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- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
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- 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
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- 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
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Abstract
本发明涉及一种咪唑并萘啶类高性能光电材料，通式结构式如下：
Description
技术领域
本发明涉及一种咪唑并萘啶类高性能光电材料及其应用，属于有机电致发光领域技术领域。
背景技术
有机发光二极管又称为有机电激光显示(Organic Light-Emitting Diode，OLED)，由美籍华裔教授邓青云在实验室中发现，由此展开了对OLED的研究。OLED显示技术具有自发光的特性，采用非常薄的有机材料涂层和玻璃基板，当有电流通过时，这些有机材料就会发光，而且OLED显示屏幕可视角度大，并且能够节省电能。
当前，OLED显示技术已经在智能手机，平板电脑等领域获得应用，进一步还将向电视等大尺寸应用领域扩展。但是，和实际的产品应用要求相比，OLED器件的发光效率，使用寿命等性能还需要进一步提升。
对于OLED发光器件提高性能的研究包括：降低器件的驱动电压，提高器件的发光效率，提高器件的使用寿命等。为了实现OLED器件的性能的不断提升，不但需要从OLED器件结构和制作工艺的创新，更需要OLED光电功能材料不断研究和创新，创制出更高性能OLED的功能材料。
构成OLED器件的OLED光电功能材料膜层至少包括两层以上结构，产业上应用的OLED器件结构，则包括空穴注入层、空穴传输层、发光层、电子注入层等多种膜层，也就是说应用于OLED器件的光电功能材料至少包含空穴注入材料、空穴传输材料、发光材料、电子注入材料等，材料类型和搭配形式具有丰富性和多样性的特点。另外，对于不同结构的OLED器件搭配而言，所使用的光电功能材料具有较强的选择性，相同的材料在不同结构器件中的性能表现，也可能完全迥异。
因此，针对当前OLED器件的产业应用要求，以及OLED器件的不同功能膜层，器件的光电特性需求，必须选择更适合，具有高性能的OLED功能材料或材料组合，才能实现器件的高效率、长寿命和低电压的综合特性。
就当前OLED显示照明产业的实际需求而言，目前OLED材料的发展还远远不够，落后于面板制造企业的要求，作为材料企业开发更高性能的有机功能材料的开发显得尤为重要。
发明内容
本发明针对现有技术存在的不足，提供一种咪唑并萘啶类高性能光电材料，该类材料制作出的OLED器件具有更高的发光强度和发光效率，能够满足面板制造企业的要求。
本发明解决上述技术问题的技术方案如下：一种咪唑并萘啶类高性能光电材料，所述的高性能光电材料的通式结构式如下：
其中，所述的Ar为取代或未取代的碳数为6-50的芳香族烃基，所述碳数为6-50的芳香族烃基为如下基团中的任意一个：苯基、联苯基、萘基、菲基、蒽基、荧蒽基、苯并蒽基、三联苯基、芘基、9,9-二甲基芴基、二苯并呋喃基、二苯并噻吩基、N-苯基咔唑基、9,9-二苯基芴基、喹啉基、3,5-二苯基三嗪基或苯并9,9-二甲基芴基。
优选的，所述的Ar选自如下基团中的任意一个：
优选的，所述的高性能光电材料选自如下化合物中的任意一个：
本发明所述的咪唑并萘啶类高性能光电材料的制备路线如下：
其中主原料以A表示，中间体以B、C、D、E、F表示，主体结构以G表示，产品以H表示；其中X为Cl、Br、I。
上述合成方法以X是Br为例，具体步骤如下：
(1)中间体B以1-氨基-2-溴-4,5-萘啶、苯甲醛为主原料，向充有氮气的500ml三口瓶中加入1-氨基-2-溴-4,5-萘啶60g(267.8mmol)、苯甲醛42.6g(401.7mmol)二甲苯300g(344.8ml)，升温至140～145℃回流保温反应，保温19h跟踪TLC反应至原料1-氨基-2-溴-4,5-萘啶反应完全，HPLC(产品B)：96.61％，反应合格后经脱溶剂，1倍乙醇重结晶烘干后得到目标产物B 63.2g，收率75.6％，HPLC：99.9％，1H NMR:δ7.46-7.56(3H,7.51(dddd,J＝8.2,7.4,1.5,0.4Hz),7.50(dd,J＝7.9,4.9Hz)),7.80(1H,tt,J＝7.4,1.7Hz),8.39(2H,dddd,J＝8.2,1.7,1.6,0.4Hz),8.72-8.79(2H,8.72(s),8.76(dd,J＝7.9,1.8Hz)),8.80(1H,s),8.96(1H,dd,J＝4.9,1.8Hz)。
元素分析结构：分子式为C15H10BrN3；LC-MS产物分子量：311.52，产物实际分子量为312.16。
(2)中间体结构C以中间体B和苯胺为主原料，向充有氮气的500ml三口瓶中加入中间体B 35g(112.1mmol)、苯胺10.4g(112.1mmol)、磷酸三钾59.5g(280mmol)、叔丁醇280g(350ml)，醋酸钯0.77g、S-phos(2-二环己基膦-2',6'-二甲氧基联苯)2.762g，料加毕，搅拌升温至60～65℃保温反应，取样跟踪HPLC，保温20h反应合格，HPLC(B)≤1.5％，反应合格后经水洗、盐酸酸化、氢氧化钠碱化、水洗脱溶剂、甲苯重结晶得到目标产物C 20.0g HPLC:99.8％，收率55％。
元素分析结构：分子式为C21H16N4；LC-MS检测产物分子量：323.88，产物实际分子量为324.38；1H NMR:δ7.07(1H,tt,J＝7.8,1.2Hz),7.23-7.45(7H,7.40(dddd,J＝8.2,7.4,1.8,0.4Hz),7.35(dddd,J＝8.2,1.3,1.2,0.5Hz),7.28(dddd,J＝8.2,7.8,1.7,0.5Hz),7.34(dd,J＝7.8,5.0Hz)),7.69(1H,tt,J＝7.4,1.4Hz),8.26(2H,dddd,J＝8.2,1.4,1.3,0.4Hz),8.50(1H,dd,J＝7.8,1.8Hz),8.58(1H,s),8.60(1H,s),8.90(1H,dd,J＝5.0,1.8Hz)。
(3)中间体D以中间体C为原料，向充有氮气的500ml三口瓶中加入中间体C20g(61.6mmol)、工业盐酸15g、工业硫酸15g，乙腈200g(256.4ml)，升温至80～85℃保温反应，保温6h反应完全，HPLC(原料C)≤1％，反应合格后经氢氧化钠碱化、水洗、脱溶剂、甲苯重结晶一次得到目标产物D11.4g，HPLC:99.85％，收率78％。
元素分析结构：分子式为C14H12N4；LC-MS检测产物分子量：326.1，产物实际分子量为236.27；1H NMR:δ6.93(1H,tt,J＝7.8,1.2Hz),7.13(2H,dddd,J＝8.2,1.2,1.2,0.5Hz),7.25(2H,dddd,J＝8.2,7.8,1.4,0.5Hz),7.50(1H,dd,J＝8.2,4.5Hz),7.98(1H,s),8.60-8.68(2H,8.66(dd,J＝4.5,1.9Hz),8.63(dd,J＝8.2,1.9Hz))。
(4)中间体F以中间体E(对溴苯甲醛)为原料，向充有氮气的250ml三口瓶中加入原料亚硫酸氢钠42.2g(405.4mmol)、自来水105.4g搅拌升温至70～75℃分批次向反应体系中加入中间体原料E(对溴苯甲醛)，控温70～75℃保温4h反应完全，反应合格后经过滤、乙醇打浆、烘干得到目标产物F 74.2g，收率95％，无需检测结构分析。
(5)主体结构G以中间体D和F为原料，向充有氮气的500ml三口瓶中加入原料D33.8g(143mmol)、原料F 45.4g(157mmol)，乙醇158.9g(201.1ml)，升温至73～78℃保温反应，同时不断向反应液液面以下鼓入空气，保温3h反应完全，HPLC(原料D)≤0.5％，反应合格后经脱溶剂、甲苯热溶水洗、脱溶剂、甲苯重结晶一次得到目标产物G 45.9g，HPLC：97.8％，收率80％。
元素分析结构：分子式为C21H13BrN4；LC-MS检测产物分子量：401.06，产物实际分子量为401.26；1H NMR:δ7.38-7.51(4H,7.42(dd,J＝7.5,4.8Hz),7.47(tdd,J＝7.5,1.7,1.4Hz),7.48(ddd,J＝8.6,1.9,0.4Hz)),7.65(2H,dddd,J＝7.5,7.4,2.1,0.4Hz),7.92(2H,dtd,J＝7.4,1.7,0.4Hz),8.35(2H,ddd,J＝8.6,1.7,0.4Hz),8.66(1H,dd,J＝7.5,1.7Hz),8.99(1H,dd,J＝4.8,1.7Hz),9.48(1H,s)。
(6)最终产物H以主体结构G和芳基硼酸为主要原料，以甲苯为溶剂，四(三苯基膦)钯或其他钯催化剂，碳酸钾水溶液提供碱性环境，控温70～80℃反应得到最终产物。
其中所述芳基硼酸为苯硼酸、4-联苯硼酸、4-溴三联苯硼酸、2-萘硼酸、1-萘硼酸、2-二苯并呋喃硼酸、1-芘硼酸。
本发明还公开了所述的咪唑并萘啶类高性能光电材料的应用：
所述的咪唑并萘啶类高性能光电材料应用于有机电致发光器件。
进一步的，所述的咪唑并萘啶类高性能光电材料作为有机电致发光器件的发光层材料。
进一步的，所述的咪唑并萘啶类高性能光电材料作为有机电致发光器件的电子传输层材料。
进一步的，所述的咪唑并萘啶类高性能光电材料中的任意一种或至少两种组合作为发光层或电子传输层材料。
本发明的有益效果是：本发明所述的咪唑并萘啶类高性能光电材料通过分子结构的特殊设计，实现了玻璃化转变温度和能量转移效率的提升，而且获得了较低的三线态能级，其热分解温度不低于363℃，甚至达到了403℃。所述咪唑并萘啶类高性能光电材料具有双偶极性，其HOMO能级和LUMO能级分别定位于不同的供电子基团和吸电子基团上，能够与相邻的空穴传输层、电子传输层相匹配，电荷和空穴传输的平衡性好，扩大了发光层中空穴和电子复合作为电子的区域，降低了激子浓度，防止器件的三线态-三线态湮灭，提高了器件效率。所述有机电致发光化合物作为发光层主体材料，使主体材料中载流子复合的区域远离发光层与空穴或者电子传输层的相邻界面，提高OLED器件的色纯度，同时能够防止激子向传输层的回传，进一步提高器件效率，尤其适用于OLED器件的红光发光主体材料，使器件的驱动电压降低至4.7V以下，电流效率提高至30～42cd/A，寿命达到39～52h。所述的咪唑并萘啶类高性能光电材料适宜用作电致发光器件的发光层主体材料或电子传输层材料，可被广泛的应用于手机、电脑、电视的显示屏领域。
附图说明
图1为应用例中所述的有机电致发光器件的结构示意图；
图中，1阳极，2空穴注入层，3空穴传输层，4放光层，5电子传输层，6电子注入层，7阴极。
具体实施方式
为使本发明的上述目的、特征和优点能够更加明显易懂，下面对本发明的具体实施方式做详细的说明。在下面的描述中阐述了很多具体细节以便于充分理解本发明。但是本发明能够以很多不同于在此描述的其它方式来实施，本领域技术人员可以在不违背本发明内涵的情况下做类似改进，因此本发明不受下面公开的具体实施例的限制。
除非另有定义，本文所使用的所有的技术和科学术语与属于本发明的技术领域的技术人员通常理解的含义相同。本文中在本发明的说明书中所使用的术语只是为了描述具体的实施方式的目的，不是旨在于限制本发明。
实施例1：化合物1
合成路线：
具体制备步骤如下：
向氮气保护500ml三口瓶中加入化合物G 25g，苯硼酸7.6g，碳酸钾21.5g，纯化水50g，甲苯200g，四(三苯基膦)钯0.359g，开启搅拌，使用油浴锅升温至75～85℃保温反应，TLC跟踪反应，大约4h反应完全，反应毕体系分层，有机相经水洗、脱溶剂、甲苯重结晶、烘干得到化合物1黄色固体18.1g，HPLC 99.8％，收率73％。
元素分析结构：分子式为C27H18N4；HPLC-MS检测产物分子量：398.0，产物实际分子量为398.46；1H NMR:δ7.49-7.63(5H,7.55(dd,J＝5.6,5.0Hz),7.54(tdd,J＝7.9,1.8,1.4Hz),7.58(tdd,J＝7.4,1.9,1.5Hz),7.58(dddd,J＝8.3,7.4,1.8,0.4Hz)),7.75(2H,dddd,J＝7.9,5.9,2.1,0.5Hz),7.92-8.05(4H,7.95(dtd,J＝5.9,1.8,0.5Hz),8.01(dddd,J＝7.9,1.9,1.5,0.4Hz)),8.30-8.38(4H,8.34(ddd,J＝8.3,2.2,0.4Hz),8.33(ddd,J＝7.8,1.9,0.4Hz)),8.69(1H,dd,J＝5.6,1.7Hz),9.18(1H,dd,J＝5.0,1.7Hz),9.50(1H,s)。
实施例2：化合物3
合成路线：
具体制备步骤如下：
向氮气保护500ml三口瓶中加入化合物G 25g，1-萘硼酸10.7g，碳酸钾21.5g，纯化水50g，甲苯200g，四(三苯基膦)钯0.359g，开启搅拌，使用油浴锅升温至75～85℃保温反应，TLC跟踪反应，大约4h反应完全，反应毕体系分层，有机相经水洗、脱溶剂、乙酸乙酯重结晶、烘干得到化合物3黄色固体21.8g，HPLC:99.68％，收率78％。
元素分析结构：分子式为C31H20N4；HPLC-MS检测产物分子量：449.03，产物实际分子量为448.52；1H NMR:δ7.55-7.73(5H,7.59(dd,J＝5.4,4.9Hz),7.61(tdd,J＝8.0,1.8,1.4Hz),7.67(ddd,J＝7.7,7.4,1.9Hz),7.60(dddd,J＝7.7,7.2,1.7,0.4Hz),7.69(ddd,J＝6.3,6.0,0.4Hz)),7.82(2H,dddd,J＝8.0,5.1,2.0,0.5Hz),7.99(2H,dtd,J＝5.1,1.8,0.5Hz),8.22(2H,ddd,J＝8.6,2.0,0.5Hz),8.27-8.34(2H,8.30(dddt,J＝6.3,2.0,1.9,0.4Hz),8.30(dtt,J＝7.2,1.9,0.4Hz)),8.37-8.47(4H,8.40(ddd,J＝6.0,2.0,0.4Hz),8.44(ddd,J＝6.5,1.8,0.5Hz),8.40(ddq,J＝7.4,1.7,0.4Hz)),8.78(1H,dd,J＝5.4,1.7Hz),9.14(1H,dd,J＝4.9,1.7Hz),9.50(1H,s)。
实施例3：化合物4
合成路线：
具体制备步骤如下：
向氮气保护500ml三口瓶中加入化合物G 25g，3-联苯硼酸12.3g，碳酸钾21.5g，纯化水50g，甲苯200g，四(三苯基膦)钯0.1799g，开启搅拌，使用油浴锅升温至75～85℃保温反应，TLC跟踪反应，大约6h反应完全，反应毕体系分层，有机相经水洗、脱溶剂、甲苯和乙醇重结晶、烘干得到化合物4黄色固体25.1g；HPLC：99.8％，收率85％。
元素分析结构：分子式为C33H22N4；LC-MS检测产物分子量：473.86，产物实际分子量为474.55；1H NMR:δ7.53-7.65(5H,7.59(dd,J＝5.4,5.0Hz),7.58(tdd,J＝7.9,1.8,1.4Hz),7.61(tdd,J＝6.2,1.8,1.6Hz),7.59(dddd,J＝7.9,6.2,1.8,0.4Hz)),7.70-7.84(3H,7.74(ddd,J＝7.5,6.3,0.5Hz),7.79(dddd,J＝8.0,5.1,2.0,0.5Hz)),7.87(2H,dddd,J＝8.0,1.8,1.5,0.4Hz),7.97(2H,dtd,J＝5.1,1.8,0.5Hz),8.17(1H,dt,J＝7.5,1.9Hz),8.28-8.36(3H,8.32(ddd,J＝8.6,2.0,0.5Hz),8.31(dt,J＝6.3,1.9Hz)),8.37-8.44(3H,8.42(ddd,J＝1.9,1.9,0.5Hz),8.40(ddd,J＝6.6,1.8,0.5Hz)),8.75(1H,dd,J＝5.4,1.7Hz),9.12(1H,dd,J＝5.0,1.7Hz),9.49(1H,s)。
实施例4：化合物10
合成路线：
具体制备步骤如下：
向氮气保护500ml三口瓶中加入化合物G 27g，9-菲硼酸14.9g，碳酸钾23.2g，纯化水54.2g，甲苯200g，醋酸钯0.1848g，S-phos(2-二环己基膦-2',6'-二甲氧基联苯)0.1923g，开启搅拌，使用油浴升温至85～90℃保温反应，TLC跟踪反应，大约7h反应完全，反应毕体系分层，有机相经水洗、脱溶剂、四氢呋喃和乙醇重结晶、烘干得到化合物10固体27.2g，HPLC:99.7％，收率81％。
元素分析结构：分子式为C35H22N4；LC-MS检测产物分子量：497.88，产物实际分子量为498.58；1H NMR:δ7.53-7.65(5H,7.59(dd,J＝5.4,5.0Hz),7.58(tdd,J＝7.9,1.8,1.4Hz),7.61(tdd,J＝6.2,1.8,1.6Hz),7.59(dddd,J＝7.9,6.2,1.8,0.4Hz)),7.70-7.84(3H,7.74(ddd,J＝7.5,6.3,0.5Hz),7.79(dddd,J＝8.0,5.1,2.0,0.5Hz)),7.87(2H,dddd,J＝8.0,1.8,1.5,0.4Hz),7.97(2H,dtd,J＝5.1,1.8,0.5Hz),8.17(1H,dt,J＝7.5,1.9Hz),8.28-8.36(3H,8.32(ddd,J＝8.6,2.0,0.5Hz),8.31(dt,J＝6.3,1.9Hz)),8.37-8.44(3H,8.42(ddd,J＝1.9,1.9,0.5Hz),8.40(ddd,J＝6.6,1.8,0.5Hz)),8.75(1H,dd,J＝5.4,1.7Hz),9.12(1H,dd,J＝5.0,1.7Hz),9.49(1H,s)。
实施例5：化合物33
合成路线：
具体制备步骤如下：
向氮气保护500ml三口瓶中加入化合物G 27g，2-二苯并呋喃硼酸，碳酸钾23.2g，纯化水54.2g，甲苯200g，醋酸钯0.1848g，S-phos(2-二环己基膦-2',6'-二甲氧基联苯)0.1923g，开启搅拌，使用油浴升温至85～90℃保温反应，TLC跟踪反应，大约3h反应完全，反应毕体系分层，有机相经水洗、脱溶剂、二氯乙烷重结晶、烘干得到化合物33固体25.6g，HPLC:99.5％，收率78％。
元素分析结构：分子式为C33H20N4O；LC-MS检测产物分子量：487.88，产物实际分子量为488.54；1H NMR:δ7.54(1H,tdd,J＝7.9,1.8,1.4Hz),7.69-7.88(6H,7.72(dd,J＝5.5,5.0Hz),7.75(ddd,J＝7.9,5.6,1.7Hz),7.74(ddd,J＝5.6,1.9,0.5Hz),7.83(ddd,J＝7.9,5.1,1.9Hz),7.75(dddd,J＝7.9,5.1,2.0,0.5Hz)),7.96(2H,dtd,J＝5.1,1.8,0.5Hz),8.17(1H,dd,J＝5.5,0.5Hz),8.35-8.49(6H,8.44(dd,J＝5.5,1.9Hz),8.40(ddd,J＝6.6,1.8,0.5Hz),8.39(ddd,J＝8.6,2.0,0.5Hz),8.46(dddd,J＝5.1,1.7,0.5,0.4Hz)),8.58(1H,dt,J＝1.9,0.4Hz),8.71(1H,dd,J＝5.5,1.7Hz),9.10(1H,dd,J＝5.0,1.7Hz),9.48(1H,s)。
实施例6：化合物37
合成路线：
具体制备步骤如下：
向氮气保护500ml三口瓶中加入化合物G 25g，1-芘硼酸15.3g，碳酸钾21.5g，纯化水50g，甲苯200g，四(三苯基膦)钯0.1799g，开启搅拌，使用油浴锅升温至75～80℃保温反应，TLC跟踪反应，大约6h反应完全，反应毕体系分层，有机相经水洗、脱溶剂、二氯乙烷重结晶、烘干得到化合物37固体21.2g，HPLC:99.6％，收率65％。
元素分析结构：分子式为C37H22N4；LC-MS检测产物分子量：523.1，产物实际分子量为522.6；1H NMR:δ7.66(1H,tdd,J＝6.8,1.8,1.4Hz),8.01-8.10(4H,8.04(dtd,J＝5.0,1.8,0.5Hz),8.06(dddd,J＝6.8,5.0,1.8,0.5Hz)),8.18(1H,tt,J＝5.0,0.5Hz),8.44(2H,ddd,J＝7.4,2.0,0.5Hz),8.53(1H,dtd,J＝5.0,1.8,0.5Hz),8.60-8.78(7H,8.76(ddt,J＝5.1,1.8,0.5Hz),8.75(ddd,J＝6.5,1.5,0.5Hz),8.72(dtd,J＝5.0,1.8,0.5Hz),8.67(ddd,J＝6.1,1.8,0.5Hz),8.63(t,J＝4.9Hz),8.76(dddd,J＝5.1,1.8,0.5,0.5Hz)),8.86-8.99(4H,8.92(ddd,J＝6.3,1.8,0.5Hz),8.89(dd,J＝5.0,1.7Hz),8.97(dt,J＝6.1,0.5Hz),8.89(dt,J＝6.3,0.6Hz)),9.13(1H,dd,J＝4.9,1.7Hz),9.35(1H,s)。
实施例7：化合物41
合成路线：
具体制备步骤如下：
向氮气保护500ml三口瓶中加入化合物G 25g，9,9-二甲基-2-芴硼酸14.8g，碳酸钾21.5g，纯化水50g，甲苯200g，醋酸钯0.1399g，三苯基膦0.3268g，开启搅拌，使用油浴升温至95～100℃保温反应，TLC跟踪反应，大约6h反应完全，反应毕体系分层，有机相经水洗、脱溶剂、甲苯重结晶、烘干得到化合物41固体21.8g，HPLC:99.7％，收率68％。
元素分析结构：分子式为C36H26N4；LC-MS检测产物分子量：514.05，产物实际分子量为514.62；1H NMR:δ7.66(1H,tdd,J＝6.8,1.8,1.4Hz),8.01-8.10(4H,8.04(dtd,J＝5.0,1.8,0.5Hz),8.06(dddd,J＝6.8,5.0,1.8,0.5Hz)),8.18(1H,tt,J＝5.0,0.5Hz),8.44(2H,ddd,J＝7.4,2.0,0.5Hz),8.53(1H,dtd,J＝5.0,1.8,0.5Hz),8.60-8.78(7H,8.76(ddt,J＝5.1,1.8,0.5Hz),8.75(ddd,J＝6.5,1.5,0.5Hz),8.72(dtd,J＝5.0,1.8,0.5Hz),8.67(ddd,J＝6.1,1.8,0.5Hz),8.63(t,J＝4.9Hz),8.76(dddd,J＝5.1,1.8,0.5,0.5Hz)),8.86-8.99(4H,8.92(ddd,J＝6.3,1.8,0.5Hz),8.89(dd,J＝5.0,1.7Hz),8.97(dt,J＝6.1,0.5Hz),8.89(dt,J＝6.3,0.6Hz)),9.13(1H,dd,J＝4.9,1.7Hz),9.35(1H,s)。
实施例8：化合物48
合成路线：
具体制备步骤如下：
向氮气保护500ml三口瓶中加入化合物G 23g，2-二苯并噻吩硼酸13.1g，碳酸钾19.8g，纯化水46.1g，甲苯230g，醋酸钯0.1287g，S-phos(2-二环己基膦-2',6'-二甲氧基联苯)0.3316g，开启搅拌，使用油浴升温至75～80℃保温反应，TLC跟踪反应，大约4h反应完全，反应毕体系分层，有机相经水洗、脱溶剂、甲苯重结晶、烘干得到化合物48固体24.9g，HPLC:99.95％，收率86％。
元素分析结构：分子式为C33H20N4S；LC-MS检测产物分子量：504.05，产物实际分子量为504.6；1H NMR:δ7.60(1H,tdd,J＝7.9,1.8,1.4Hz),7.66-7.87(5H,7.72(dd,J＝5.5,5.0Hz),7.70(ddd,J＝7.5,5.1,1.8Hz),7.75(dddd,J＝7.9,5.9,2.0,0.5Hz),7.83(ddd,J＝7.5,7.0,1.9Hz)),7.89-7.99(3H,7.96(dddd,J＝5.9,1.8,1.8,0.5Hz),7.92(dd,J＝7.7,2.1Hz)),8.31-8.43(5H,8.34(ddd,J＝7.0,1.8,0.5Hz),8.39(ddd,J＝6.5,1.8,0.5Hz),8.40(ddd,J＝8.6,2.0,0.5Hz)),8.58-8.63(2H,8.62(dd,J＝2.1,0.5Hz),8.61(ddt,J＝5.1,1.9,0.5Hz)),8.69-8.77(2H,8.74(dt,J＝7.7,0.5Hz),8.71(dd,J＝5.5,1.7Hz)),9.10(1H,dd,J＝5.0,1.7Hz),9.48(1H,s)。
实施例9：化合物50
合成路线：
具体制备步骤如下：
向氮气保护500ml三口瓶中加入化合物G 23g，N-苯基-3-咔唑硼酸16.5g，碳酸钾19.8g，水46.1g，甲苯200g，醋酸钯0.1287g，三环己基膦5.3g，开启搅拌，使用油浴升温至75～80℃保温反应，TLC跟踪反应，大约4h反应完全，反应毕体系分层，有机相经水洗、脱溶剂、甲苯重结晶、烘干得到化合物50固体24.5g；HPLC:99.99％，收率73％。
元素分析结构：分子式为C39H25N5；LC-MS检测产物分子量：563.5，产物实际分子量为563.65；1H NMR:δ7.41(1H,dd,J＝8.7,2.0Hz),7.50-7.79(9H,7.67(ddd,J＝8.0,5.1,1.8Hz),7.60(tdd,J＝7.8,1.7,1.5Hz),7.56(tdd,J＝7.8,1.8,1.3Hz),7.67(dddd,J＝7.8,6.7,1.9,0.5Hz),7.73(ddd,J＝8.0,5.1,2.0Hz),7.74(dddd,J＝7.8,6.0,1.9,0.5Hz),7.68(t,J＝5.0Hz)),7.92-7.98(4H,7.95(dddd,J＝6.0,1.8,1.7,0.5Hz),7.95(dtd,J＝6.7,1.7,0.4Hz)),8.26(1H,dd,J＝8.7,0.5Hz),8.30-8.39(3H,8.32(ddd,J＝5.1,1.8,0.5Hz),8.36(ddd,J＝8.4,2.0,0.5Hz)),8.44-8.52(3H,8.49(ddd,J＝5.2,2.0,0.5Hz),8.46(ddt,J＝5.1,2.0,0.5Hz)),8.71(1H,dd,J＝5.0,1.7Hz),9.03-9.10(2H,9.08(dd,J＝5.0,1.7Hz),9.05(ddd,J＝2.0,0.5,0.5Hz)),9.47(1H,s)。
实施例10：化合物58
合成路线：
具体制备步骤如下：
向氮气保护500ml三口瓶中加入化合物G 25g，8-喹啉硼酸10.8g，碳酸钾21.5g，水50g，甲苯200g，醋酸钯0.1399g，三苯基膦0.3268g，开启搅拌，使用油浴锅升温至75～80℃保温反应，TLC跟踪反应，大约5h反应完全，反应毕体系分层，有机相经水洗、脱溶剂、甲苯重结晶、烘干得到化合物58固体19.9g，HPLC:99.96％；收率71％。
元素分析结构：分子式为C30H19N5；LC-MS检测产物分子量：448.9，产物实际分子量为449.51；1H NMR:δ7.59-7.66(2H,7.63(dd,J＝5.3,4.9Hz),7.63(tdd,J＝7.9,1.8,1.4Hz)),7.76-7.94(4H,7.80(ddd,J＝6.5,5.1,0.4Hz),7.84(dddd,J＝7.9,5.1,2.1,0.5Hz),7.90(ddd,J＝7.7,7.7,0.4Hz)),8.00(2H,dtd,J＝5.1,1.8,0.5Hz),8.33-8.42(3H,8.36(ddd,J＝7.8,2.0,0.5Hz),8.39(dddd,J＝6.5,1.5,1.4,0.4Hz)),8.44-8.51(3H,8.47(ddd,J＝6.5,1.8,0.5Hz),8.47(dtd,J＝7.7,1.4,0.4Hz)),8.78-8.85(2H,8.80(dd,J＝5.3,1.7Hz),8.82(dd,J＝7.7,1.5Hz)),9.08(1H,dd,J＝5.1,1.5Hz),9.16(1H,dd,J＝4.9,1.7Hz),9.51(1H,s)。
实施例11：化合物69
合成路线：
具体制备步骤如下：
向氮气保护500ml三口瓶中加入化合物G 25g，3,5-二苯基三嗪硼酸17.3g，碳酸钾21.5g，纯化水50g，甲苯200g，醋酸钯0.1399g，S-phos(2-二环己基膦-2',6'-二甲氧基联苯)0.2968g，开启搅拌，使用油浴升温至85～90℃保温反应，TLC跟踪反应，大约8h反应完全，反应毕体系分层，有机相经水洗、脱溶剂、甲苯重结晶、烘干得到化合物69固体23.4g；HPLC:99.95％，收率68％。
元素分析结构：分子式为C36H23N7；LC-MS检测产物分子量：552.9，产物实际分子量为553.61；1H NMR:δ7.60-7.80(5H,7.75(dddd,J＝8.4,7.5,1.6,0.5Hz),7.65(tdd,J＝8.0,1.8,1.4Hz)),7.89-8.04(6H,7.94(tdd,J＝7.5,1.7,1.5Hz),7.95(dddd,J＝8.0,5.1,2.1,0.4Hz),8.02(dddd,J＝5.1,1.8,1.8,0.5Hz)),8.42(4H,dddd,J＝8.4,1.7,1.6,0.4Hz),8.52(2H,ddd,J＝8.7,2.0,0.5Hz),8.62(2H,ddd,J＝7.2,1.5,0.5Hz),8.71(1H,t,J＝4.9Hz),8.85(1H,dd,J＝5.0,1.7Hz),9.12(1H,dd,J＝4.9,1.7Hz),9.37(1H,s)。
应用例1：
本应用例提供一种有机电致发光器件，结构示意图如图1所示，包括自下而上依次层叠的阳极1、空穴注入层2、空穴传输层3、发光层4、电子传输层5、电子注入层6和阴极7。具体为：氧化铟锡(ITO)阳极、10nm空穴注入层(HIL)/120nm空穴传输层(HTL)/40nm发光层/40nm电子传输层(ETL)/1nm电子注入层(EIL)/金属A1阴极80nm。
其中，空穴注入层的材料选用HAT(CN)6，结构如下：
空穴传输层的材料选用如下所示结构的化合物：
发光层选用本发明实施例1提供的有机电致发光化合物1作为主体材料，化合物(piq)2Ir(acac)作为客体材料，所述主体材料和客体材料的掺杂质量比为97:3；化合物(piq)2Ir(acac)的结构如下：
电子传输层的材料选用如下所述结构的化合物：
电子注入层的材料为LiF(氟化锂)。
有机电致发光器件的具体制备方法如下：
(1)基板清理：将涂布了ITO透明电机基板在水性清洗剂(所述水性清洗剂的成分及浓度：乙二醇类溶剂≤10wt％，三乙醇胺≤1wt％)中超声处理，在去离子水中冲洗，在丙酮与乙醇的混合溶剂(体积比1:1)中超声除油，在洁净环境下烘烤至完全除去水分，然后用紫外光和臭氧清洗；
(2)蒸镀：把上述带有阳极层的玻璃基片置于真空腔内，抽真空至1×10-6至2×10-4Pa，在上述阳极层膜上真空蒸镀HAT(CN)6作为空穴注入层，蒸镀速率为0.1nm/s，蒸镀厚度为10nm；
(3)在空穴注入层之上蒸镀空穴传输层，蒸镀速率为0.1nm/s，蒸镀膜厚为120nm；
(4)在空穴传输层之上蒸镀发光层，以共蒸的方式真空蒸镀发光主体材料和客体材料，主体材料蒸镀速率为0.09nm/s，客体材料蒸镀速率为0.01nm/s，蒸镀总膜厚为40nm；
(5)在发光层之上真空蒸镀一层电子传输层，其蒸镀速率为0.1nm/s，蒸镀总膜厚为40nm；
(6)在电子传输层上真空蒸镀一层电子注入层，其蒸镀速率为0.05nm/s，蒸镀总膜厚为1nm；
(7)Al(铝)作为器件的阴极层，蒸镀速率为0.1nm/s，蒸镀总膜厚为80nm。应用例2～11相较于应用例1仅替换发光层的主体材料，具体详见表1和表2
对比例1：
本对比例与应用例1的区别在于，将发光层中的有机电致发光化合物1，用等质量的化合物PPDC
替换。
对比例2：
本对比例与应用例1的区别在于，将发光层中的有机电致发光化合物1用等质量的对比化合物M1
替换。
对比例3：
本对比例与应用例1的区别在于，将发光层中的有机电致发光化合物1用等质量的对比化合物M2
替换。
测试例1
对本发明实施例提供的有机电致发光化合物进行如下测试：
(1)热分解温度测试：
使用热重分析仪(TGA，美国TATGA55)对实施例提供的有机电致发光化合物进行热分解温度测试，测试范围室温至600℃，升温速率10℃/min，氮气氛围下，重量损失5％的温度定义为分解温度，用Td(℃)表示。
(2)HOMO能级和LUMO能级测试：
使用电化学工作站利用循环伏安法(CV，上海辰华CHI-600E)对实施例提供的有机电致发光化合物的HOMO与LUMO能级进行测试，以铂丝(Pt)为对电极，银/氯化银(Ag/AgCl)为参比电极。在氮气氛围下，在含有0.1M四丁基六氟磷酸铵的二氯甲烷电解液中以100mV/s的扫描速率进行测试，以二茂铁进行电位标定，设定二茂铁的电位在真空状态下的绝对能级为-4.8eV：
其中，
表示氧化电位，
表示还原电位，EFc/Fc表示二茂铁电位。
(3)三线态能级测试：
使用荧光分光光度计(日立F-4600)在溶液状态(溶剂为甲苯，浓度2×10-5mol/L)、-78℃条件下测试实施例提供的有机电致发光化合物的三线态能级ET1，计算方式为：ET1＝1240/(最短紫外光/可见光吸收波长)。
上述测试实验的具体结果如表1所示：
表1
从表1的数据可知，本发明提供的有机电致发光化合物具有高的热分解温度，其热分解温度可以达到364～379℃，使所述有机电致发光化合物作为发光材料在器件中保持优异的热稳定性，使得器件在制备过程中不易分解破坏；三线态能级高，HOMO与LUMO能级差较小，化合物的HOMO能级和LUMO能级与相邻的传输层相匹配，使OLED器件具有较低的驱动电压。
测试例2
针对应用例和对比例的有机电致发光器件进行如下测试：器件的电流、电压、亮度、发光光谱等特性采用PR650光谱扫描亮度计和Keithley K 2400数字源表系统同步测试。
测试条件：电流密度为10mA/cm2，25℃；
寿命测试：器件亮度下降至原始亮度的95％时记录时间(以小时计)。
测试结果如表2所示：
表2
根据表2的数据可知，应用例1～11中使用本发明提供的有机电致发光化合物作为发光层主体材料的有机电致发光器件驱动电压较低，其驱动低压为4.4～4.6V，电流效率较高，可以达到34～39cd/A，工作寿命为39～48h；而对比例的工作电压为5.1V，电流效率为16～20cd/A，工作寿命仅有23～29h，其发光性能明显比应用例差。由此可见，本发明提供的特定结构的有机电致发光化合物作为发光层主体材料可以有效降低器件的工作电压，同时提升器件的发光效率和工作寿命。
以上所述实施例的各技术特征可以进行任意的组合，为使描述简洁，未对上述实施例中的各个技术特征所有可能的组合都进行描述，然而，只要这些技术特征的组合不存在矛盾，都应当认为是本说明书记载的范围。
以上所述实施例仅表达了本发明的几种实施方式，其描述较为具体和详细，但并不能因此而理解为对发明专利范围的限制。应当指出的是，对于本领域的普通技术人员来说，在不脱离本发明构思的前提下，还可以做出若干变形和改进，这些都属于本发明的保护范围。因此，本发明专利的保护范围应以所附权利要求为准。
Claims (5)
1.一种咪唑并萘啶类光电材料，其特征在于，所述的光电材料的通式结构式如下：
其中，所述的Ar为碳数为6-50的芳香烃基，所述碳数为6-50的芳香烃基为如下基团中的任意一个：苯基、联苯基、萘基、菲基、蒽基、荧蒽基、苯并蒽基、三联苯基、芘基、9,9-二甲基芴基、二苯并呋喃基、二苯并噻吩基、N-苯基咔唑基、9,9-二苯基芴基、喹啉基、3,5-二苯基三嗪基或苯并9,9-二甲基芴基。
2.根据权利要求1所述的一种咪唑并萘啶类光电材料，其特征在于，所述的Ar选自如下基团中的任意一个：
3.根据权利要求1所述的一种咪唑并萘啶类光电材料，其特征在于，所述的光电材料选自如下化合物中的任意一个：
4.一种根据权利要求1-3任一项所述的一种咪唑并萘啶类光电材料的应用，其特征在于，所述的咪唑并萘啶类光电材料应用于有机电致发光器件。
5.根据权利要求4所述的一种咪唑并萘啶类光电材料的应用，其特征在于，所述的咪唑并萘啶类光电材料作为有机电致发光器件的发光层材料。
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