CN106467523B - 一种有机芳香化合物及其应用 - Google Patents

一种有机芳香化合物及其应用 Download PDF

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CN106467523B
CN106467523B CN201610619828.4A CN201610619828A CN106467523B CN 106467523 B CN106467523 B CN 106467523B CN 201610619828 A CN201610619828 A CN 201610619828A CN 106467523 B CN106467523 B CN 106467523B
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CN106467523A (zh
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王立春
叶中华
李崇
张兆超
徐凯
于凯朝
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Jiangsu Sunera Technology Co Ltd
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Jiangsu Sanyue Optoelectronic Technology Co Ltd
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Abstract

本发明公开了一种以吖啶螺蒽酮为核心的有机芳香化合物及其在有机电致发光器件上的应用，该化合物以吖啶螺蒽酮为核心，具有分子间不易结晶、不易聚集、具有良好成膜性的特点。将本发明化合物作为发光层材料应用于有机电致发光器件上，应用本发明化合物的有机电致发光器件具有良好的光电性能表现，可以更好的适应和满足面板制造企业的应用要求。

Description

一种有机芳香化合物及其应用
技术领域
本发明涉及半导体技术领域，尤其是涉及一种吖啶螺螺蒽酮为核心的有机芳香化合物，以及其作为发光层材料在有机发光二极管上的应用。
背景技术
有机电致发光(OLED:Organic Light Emission Diodes)器件技术既可以用来制造新型显示产品，也可以用于制作新型照明产品，有望替代现有的液晶显示和荧光灯照明，应用前景十分广泛。
OLED发光器件犹如三明治的结构，包括电极材料膜层，以及夹在不同电极膜层之间的有机功能材料，各种不同功能材料根据用途相互叠加在一起共同组成OLED发光器件。作为电流器件，当对OLED发光器件的两端电极施加电压，并通过电场作用有机层功能材料膜层中的正负电荷，正负电荷进一步在发光层中复合，即产生OLED电致发光。
有机发光二极管(OLEDs)在大面积平板显示和照明方面的应用引起了工业界和学术界的广泛关注。然而，传统有机荧光材料只能利用电激发形成的25％单线态激子发光，器件的内量子效率较低(最高为25％)。外量子效率普遍低于5％，与磷光器件的效率还有很大差距。尽管磷光材料由于重原子中心强的自旋-轨道耦合增强了系间窜越，可以有效利用电激发形成的单线态激子和三线态激子发光，使器件的内量子效率达100％。但磷光材料存在价格昂贵，材料稳定性较差，器件效率滚落严重等问题限制了其在OLEDs的应用。热激活延迟荧光(TADF)材料是继有机荧光材料和有机磷光材料之后发展的第三代有机发光材料。该类材料一般具有小的单线态-三线态能级差(△EST)，三线态激子可以通过反系间窜越转变成单线态激子发光。这可以充分利用电激发下形成的单线态激子和三线态激子，器件的内量子效率可以达到100％。同时，材料结构可控，性质稳定，价格便宜无需贵重金属，在OLEDs领域的应用前景广阔。
虽然理论上TADF材料可以实现100％的激子利用率，但实际上存在如下问题:(1)设计分子的T1和S1态具有强的CT特征，非常小的S1-T1态能隙，虽然可以通过TADF过程实现高T1→S1态激子转化率，但同时导致低的S1态辐射跃迁速率，因此，难于兼具(或同时实现)高激子利用率和高荧光辐射效率；(2)即使已经采用掺杂器件减轻T激子浓度猝灭效应，大多数TADF材料的器件在高电流密度下效率滚降严重。
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显得尤为重要。
发明内容
针对现有技术存在的上述问题，本申请人提供了一种有机芳香化合物及其应用。本发明化合物基于TADF机理以吖啶螺蒽酮为核心，作为发光层材料应用于有机电致发光器件，本发明制作的器件具有良好的光电性能，能够满足面板制造企业的要求。
本发明的技术方案如下：
本申请人提供了一种有机发光芳香化合物，所述化合物的结构如通式(1)所示：
通式(1)中，Ar表示-Ar1-R或者-R；其中，Ar1表示苯基、二联苯基、萘基或者蒽基；
其中，R采用通式(2)、通式(3)、通式(4)或通式(5)表示：
其中，R1可表示为通式(6)所示结构；R2选取氢或通式(6)所示结构：
a为或X2、X3分别为氧原子、硫原子、硒原子、C1-10直链或支链烷基取代的亚烷基、芳基取代的亚烷基、烷基或芳基取代的叔胺基中的一种；a与CL1-CL2键、CL2-CL3键、CL3-CL4键、CL4-CL5键、CL‘1-CL’2键、CL‘2-CL’3键、CL‘3-CL’4键或CL‘4-CL’5键连接；
R3、R5分别独立的表示为碳原子数1-6的烷基或环烷基、取代或者未取代的芳基、芳胺基、或杂芳基中的一种；
R4表示为氢或者碳原子数1-6的烷基或环烷基、取代或未取代的芳基、芳胺基、或杂芳基中的一种；
X、Y分别独立的表示为氧原子、硫原子、硒原子、C1-10直链或支链烷基取代的亚烷基、芳基取代的亚烷基、烷基或芳基取代的叔胺基中的一种。
特别的，当a表示且与CL4-CL5键或CL‘4-CL’5键连接时，X1和X2的位置重叠，只取X1或者X2；X3表示为氧原子、硫原子、硒原子、C1-10直链或支链烷基取代的亚烷基、芳基取代的亚烷基、烷基或芳基取代的叔胺基中的一种。
优选的，所述化合物的结构为通式(7)、通式(8)、通式(9)或者通式(10)中的任一种：
优选的，所述R3、R4、R5分别独立的表示取代或未取代的苯基、二苯胺基、吡啶基、二联苯基、三联苯基、蒽基、菲基、三嗪基、嘧啶基、喹啉基、二苯并呋喃基、9,9-二甲基芴基、9,9-二苯基芴基、咔唑基、苯并咔唑基、二苯并噻吩基、丫啶基、吲哚并咔唑基、吩噁嗪基、或噻噁嗪基中的一种。
优选的，所述化合物的具体结构为：
中的任一种。
本申请人还提供了一种包含所述化合物的发光器件，所述化合物作为发光层主体或者掺杂材料，用于制作有机电致发光器件。
本申请人还提供了一种制备所述化合物的方法，制备过程中发生的反应方程式是：
具体的制备过程是：
称取Ar—Br和吖啶螺蒽酮，用甲苯溶解；再加入Pd2(dba)3、三叔丁基膦、叔丁醇钠；在惰性气氛下，将上述反应物的混合溶液于反应温度95～110℃，反应10～24小时，冷却并过滤反应溶液，滤液旋蒸，过硅胶柱，得到目标产物；所述Ar—Br与吖啶螺蒽酮的摩尔比为1:2.0～3.0，Pd2(dba)3与Ar—Br的摩尔比为0.006～0.02:1，三叔丁基膦与Ar—Br的摩尔比为0.006～0.02:1，叔丁醇钠与Ar—Br的摩尔比为1.0～3.0:1。
本发明有益的技术效果在于：
本发明化合物以吖啶螺蒽酮为母核，氮原子上再连接一个芳香杂环基团，破坏了分子对称性，从而破坏分子的结晶性，避免了分子间的聚集作用，分子中多为刚性基团，具有好的成膜性和荧光量子效率，可以作为发光层掺杂材料使用；所述化合物结构分子内包含电子给体(donor,D)与电子受体(acceptor,A)的组合可以增加轨道重叠、提高发光效率，同时连接芳香杂环基团以获得HOMO、LUMO空间分离的电荷转移态材料，实现小的S1态和T1态的能级差，从而在热刺激条件下实现反向系间窜越，适合作为发光层主体材料使用。
本发明所述化合物可作为发光层材料应用于OLED发光器件制作，并且分别作为发光层主体材料或掺杂材料，均可以获得良好的器件表现，器件的电流效率，功率效率和外量子效率均得到很大改善；同时，对于器件寿命提升非常明显。
本发明所述化合物材料在OLED发光器件中具有良好的应用效果，具有良好的产业化前景。
附图说明
图1为本发明化合物应用的器件结构示意图；
其中，1为透明基板层，2为ITO阳极层，3为空穴注入层，4为空穴传输层，5为发光层，6为电子传输层，7为电子注入层，8为阴极反射电极层。
具体实施方式
下面结合附图和实施例，对本发明进行具体描述。
实施例1：化合物01的合成
现提供该化合物的具体合成路线：
250ml的四口瓶，在通入氮气的气氛下，加入0.012mol中间体A，0.01mol吖啶螺蒽酮，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，250ml甲苯，加热回流24小时，取样点板，反应完全，自然冷却，过滤，滤液旋蒸，过硅胶柱，得到目标产物，纯度98.6％，收率65.4％。
元素分析结构(分子式C50H32N2O3)：理论值C,84.73；H,4.55；N,3.95；O,6.77；测试值：C,84.57；H,4.45；N,3.87；O,7.11。
HPLC-MS：材料分子量为708.80，实测分子量708.40。
实施例2：化合物06的合成
现提供该化合物的具体合成路线：
250ml的四口瓶，在通入氮气的气氛下，加入0.012mol中间体B，0.01mol吖啶螺蒽酮，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，250ml甲苯，加热回流24小时，取样点板，反应完全，自然冷却，过滤，滤液旋蒸，过硅胶柱，得到目标产物，纯度98.5％，收率65.7％。
元素分析结构(分子式C59H41N3O1)：理论值C,87.70；H,5.11；N,5.20；O,1.98；测试值：C,87.60；H,5.04；N,5.09；O,2.27。
HPLC-MS：材料分子量为807.98，实测分子量807.67。
实施例3：化合物16的合成
现提供该化合物的具体合成路线：
250ml的四口瓶，在通入氮气的气氛下，加入0.012mol中间体C，0.01mol吖啶螺蒽酮，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，250ml甲苯，加热回流24小时，取样点板，反应完全，自然冷却，过滤，滤液旋蒸，过硅胶柱，得到目标产物，纯度97.8％，收率70.1％。
元素分析结构(分子式C56H34N2O3)：理论值C,85.91；H,4.38；N,3.58；O,6.13；测试值：C,85.78；H,4.43；N,3.54；O,6.25。
HPLC-MS：材料分子量为782.88，实测分子量782.95。
实施例4：化合物13的合成
现提供该化合物的具体合成路线：
250ml的四口瓶，在通入氮气的气氛下，加入0.012mol中间体D，0.01mol吖啶螺蒽酮，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，250ml甲苯，加热回流24小时，取样点板，反应完全，自然冷却，过滤，滤液旋蒸，过硅胶柱，得到目标产物，纯度98.5％，收率62.8％。
元素分析结构(分子式C65H45N3O2)：理论值C,86.74；H,5.04；N,4.67；O,3.56；测试值：C,86.54；H,4.98；N,4.65；O,3.83。
HPLC-MS：材料分子量为900.07，实测分子量900.15。
实施例5：化合物18的合成
现提供该化合物的具体合成路线：
250ml的四口瓶，在通入氮气的气氛下，加入0.012mol中间体E，0.01mol吖啶螺蒽酮，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，150ml甲苯，加热回流24小时，取样点板，反应完全，自然冷却，过滤，滤液旋蒸，过硅胶柱，得到目标产物，纯度97.3％，收率61.8％。
元素分析结构(分子式C74H55N3O2)：理论值C,87.29；H,5.44；N,4.13；O,3.14；测试值：C,87.08；H,5.60；N,4.05；O,3.27。
HPLC-MS：材料分子量为1018.25，实测分子量1018.07。
实施例6：化合物20的合成
现提供该化合物的具体合成路线：
250ml的四口瓶，在通入氮气的气氛下，加入0.012mol中间体F，0.01mol吖啶螺蒽酮，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，250ml甲苯，加热回流24小时，取样点板，反应完全，自然冷却，过滤，滤液旋蒸，过硅胶柱，得到目标产物，纯度98.6％，收率58.9％。
元素分析结构(分子式C66H48N2O2S)：理论值C,84.95；H,5.18；N,3.00；O,3.43；S,3.44；测试值：C,84.87；H,5.21；N,3.04；O,3.50；S,3.38
HPLC-MS：材料分子量为933.16，实测分子量933.10。
实施例7：化合物21的合成
现提供该化合物的具体合成路线：
250ml的四口瓶，在通入氮气的气氛下，加入0.012mol中间体G，0.01mol吖啶螺蒽酮，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，250ml甲苯，加热回流24小时，取样点板，反应完全，自然冷却，过滤，滤液旋蒸，过硅胶柱，得到目标产物，纯度98.6％，收率65.4％。
元素分析结构(分子式C68H43N3O2)：理论值C,87.44；H,4.64；N,4.50；O,3.43；测试值：C,87.50；H,4.71；N,4.45；O,3.34。
HPLC-MS：材料分子量为934.09，实测分子量934.01。
实施例8：化合物27的合成
现提供该化合物的具体合成路线：
250ml的四口瓶，在通入氮气的气氛下，加入0.012mol中间体H，0.01mol吖啶螺蒽酮，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，250ml甲苯，加热回流24小时，取样点板，反应完全，自然冷却，过滤，滤液旋蒸，过硅胶柱，得到目标产物，纯度98.1％，收率66.7％。
元素分析结构(分子式C68H40N2O4)：理论值C,86.06；H,4.25；N,2.95；O,6.74；测试值：C,85.95；H,4.15；N,3.01；O,6.89。
HPLC-MS：材料分子量为949.06，实测分子量949.12。
实施例9：化合物30的合成
现提供该化合物的具体合成路线：
250ml的四口瓶，在通入氮气的气氛下，加入0.012mol中间体I，0.01mol吖啶螺蒽酮，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，250ml甲苯，加热回流24小时，取样点板，反应完全，自然冷却，过滤，滤液旋蒸，过硅胶柱，得到目标产物，纯度98.1％，收率66.7％。
元素分析结构(分子式C82H62N4O)：理论值C,87.98；H,5.58；N,5.01；O,1.43；测试值：C,87.86；H,5.55；N,4.87；O,1.72。
HPLC-MS：材料分子量为1119.40，实测分子量1119.28。
实施例10：化合物33的合成
现提供该化合物的具体合成路线：
250ml的四口瓶，在通入氮气的气氛下，加入0.012mol中间体J，0.01mol吖啶螺蒽酮，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，250ml甲苯，加热回流24小时，取样点板，反应完全，自然冷却，过滤，滤液旋蒸，过硅胶柱，得到目标产物，纯度98.1％，收率66.7％。
元素分析结构(分子式C63H43N3O2)：理论值C,86.57；H,4.96；N,4.81；O,3.66；测试值：C,86.50；H,4.86；N,4.95；O,3.69。
HPLC-MS：材料分子量为874.03，实测分子量873.95。
实施例11：化合物43的合成
现提供该化合物的具体合成路线：
250ml的四口瓶，在通入氮气的气氛下，加入0.012mol中间体K，0.01mol吖啶螺蒽酮，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，250ml甲苯，加热回流24小时，取样点板，反应完全，自然冷却，过滤，滤液旋蒸，过硅胶柱，得到目标产物，纯度97.6％，收率61.7％。
元素分析结构(分子式C69H47N3O)：理论值C,88.72；H,5.07；N,4.50；O,1.71；测试值：C,88.68；H,4.89；N,4.60；O,1.83。
HPLC-MS：材料分子量为934.13，实测分子量934.05。
实施例12：化合物56的合成
250ml的四口瓶，在通入氮气的气氛下，加入0.012mol中间体L，0.01mol吖啶螺蒽酮，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，250ml甲苯，加热回流24小时，取样点板，反应完全，自然冷却，过滤，滤液旋蒸，过硅胶柱，得到目标产物，纯度98.6％，收率61.3％。
元素分析结构(分子式C78H53N3O)：理论值C,89.37；H,5.10；N,4.01；O,1.53；测试值：C,89.29；H,5.18；N,3.97；O,1.56。
HPLC-MS：材料分子量为1048.27，实测分子量1048.35。
本发明化合物可以作为发光层材料使用，对本发明化合物09、化合物21、现有材料mCP分别进行热性能、发光光谱、荧光量子效率以及循环伏安稳定性的测定，检测结果如表1所示。
表1
注：热失重温度Td是在氮气气氛中失重1％的温度，在日本岛津公司的TGA-50H热重分析仪上进行测定，氮气流量为20mL/min；λPL是样品溶液荧光发射波长，利用日本拓普康SR-3分光辐射度计测定；Φf是固体粉末荧光量子效率(利用美国海洋光学的Maya2000Pro光纤光谱仪，美国蓝菲公司的C-701积分球和海洋光学LLS-LED光源组成的测试固体荧光量子效率测试系统，参照文献Adv.Mater.1997，9，230-232的方法进行测定)；循环伏安稳定性是通过循环伏安法观测材料的氧化还原特性来进行鉴定；测试条件：测试样品溶于体积比为2:1的二氯甲烷和乙腈混合溶剂，浓度1mg/mL，电解液是0.1M的四氟硼酸四丁基铵或六氟磷酸四丁基铵的有机溶液。参比电极是Ag/Ag+电极，对电极为钛板，工作电极为ITO电极，循环次数为20次。
由上表数据可知，本发明化合物具有较好的氧化还原稳定性，较高的热稳定性，适合作为发光层的主体材料；同时，本发明化合物具有合适的发光光谱，较高的Φf，使得应用本发明化合物作为掺杂材料的OLED器件效率和寿命得到提升。
以下通过对比例1、2和实施例13～24详细说明本发明合成的材料在OLED器件上的应用效果。所述实施例13～24与对比例1、2相比，所述器件的制作工艺完全相同，并且所采用了相同的基板材料和电极材料，电极材料的膜厚也保持一致，所不同的是对器件中所使用的部分材料进行了一些调整，对比例1、2使用了本发明所述部分OLED材料。
对比例1
透明玻璃基板1采用透明材料。对ITO阳极层2(膜厚为150nm)进行洗涤，即依次进行碱洗涤、纯水洗涤、干燥后再进行紫外线-臭氧洗涤以清除透明ITO表面的有机残留物。
在进行了上述洗涤之后的ITO阳极层2上，利用真空蒸镀装置，蒸镀HAT-CN，其膜厚为10nm，这层有机材料作为空穴注入层3使用。紧接着蒸镀60nm厚度的TCTA(4,4',4”-三(咔唑-9-基)三苯胺)作为空穴传输层4。
上述空穴传输材料蒸镀结束后，制作OLED发光器件的发光层5，其结构包括OLED发光层5所使用材料mCP【4,4'-二(9-咔唑)联苯】作为主体材料，GD-19作为掺杂材料，掺杂比例为5％重量比，发光层膜厚为25nm。
在上述发光层5之后，继续真空蒸镀电子传输层材料为Alq3(8-羟基喹啉铝)。该材料的真空蒸镀膜厚为30nm，此层为电子传输层6。
在电子传输层6上，通过真空蒸镀装置，制作膜厚为1nm的氟化锂(LiF)层，此层为电子注入层7。
在电子注入层7上，通过真空蒸镀装置，制作膜厚为80nm的铝(Al)层，此层为阴极反射电极层8使用。各层材料结构如下所示：
所制作的OLED发光器件器件结构如表2所示，测试结果如表3所示。
对比例2
本对比例与与对比例1不同之处在于：OLED发光器件的发光层5中的GD-19改变为实Ir(ppy)3。所制作的OLED发光器件器件结构如表2所示，测试结果如表3所示。
如上所述地完成OLED发光器件后，用公知的驱动电路将阳极和阴极连接起来，测量器件的发光效率，发光颜色，外部量子效率以及器件寿命(LT95：亮度衰减到初始亮度的95％)。
实施例13
本实施例与对比例1不同之处在于：OLED发光器件的发光层5中的mCP改变为化合物06。所制作的OLED发光器件器件结构如表2所示，测试结果如表3所示。
实施例14
本实施例与对比例1同之处在于：OLED发光器件的发光层5中的mCP改变为化合物16。所制作的OLED发光器件器件结构如表2所示，测试结果如表3所示。
实施例15
本实施例与对比例2不同之处在于：OLED发光器件的发光层5中的mCP改变化合物20。所制作的OLED发光器件器件结构如表2所示，测试结果如表3所示。
实施例16
本实施例与对比例3不同之处在于：OLED发光器件的发光层5中的mCP改变为化合物27。所制作的OLED发光器件器件结构如表2所示，测试结果如表3所示。
实施例17
本实施例与对比例3不同之处在于：OLED发光器件的发光层5中的mCP改变为化合物33。所制作的OLED发光器件器件结构如表2所示，测试结果如表3所示。
表2
表3
实施例18
本实施例与对比例1不同之处在于：OLED发光器件的发光层5中的GD-19改变化合物01。所制作的OLED发光器件器件结构如表4所示，测试结果如表5所示。
实施例19
本实施例与对比例1不同之处在于：OLED发光器件的发光层5中的GD-19改变化合物13。所制作的OLED发光器件器件结构如表4所示，测试结果如表5所示。
实施例20
本实施例与对比例1不同之处在于：OLED发光器件的发光层5中的GD-19改变化合物18。所制作的OLED发光器件器件结构如表4所示，测试结果如表5所示。
实施例21
本实施例与对比例1不同之处在于：OLED发光器件的发光层5中的GD-19改变化合物21。所制作的OLED发光器件器件结构如表4所示，测试结果如表5所示。
实施例22
本实施例与对比例1不同之处在于：OLED发光器件的发光层5中的GD-19改变化合物30。所制作的OLED发光器件器件结构如表4所示，测试结果如表5所示。
实施例23
本实施例与对比例1不同之处在于：OLED发光器件的发光层5中的GD-19改变化合物43。所制作的OLED发光器件器件结构如表4所示，测试结果如表5所示。
实施例24
本实施例与对比例1不同之处在于：OLED发光器件的发光层5中的GD-19改变化合物56。所制作的OLED发光器件器件结构如表4所示，测试结果如表5所示。
表4
表5
由表3和表5的结果可以看出，本发明所述化合物作为主体材料或者掺杂材料应用于OLED发光器件制作，并且可以获得良好的器件表现。器件的发光效率、外量子效率均得到很大改善；同时器件寿命提升非常明显。本发明所述化合物在OLED发光器件中具有良好的应用效果，并具有良好的产业化前景。
虽然已通过实施例和优选实施方式公开了本发明，但应理解，本发明不限于所公开的实施方式。相反，本领域技术人员应明白，其意在涵盖各种变型和类似的安排。因此，所附权利要求的范围应与最宽的解释相一致以涵盖所有这样的变型和类似的安排。

Claims (6)

1.一种有机发光芳香化合物，其特征在于所述化合物的结构如通式(1)所示：
通式(1)中，Ar表示Ar1R或者R；其中，Ar1表示苯基、二联苯基、萘基或者蒽基；
其中，R采用通式(2)、通式(3)、通式(4)或通式(5)表示：
其中，R1可表示为通式(6)所示结构；R2选取氢或通式(6)所示结构：
a为X2、X3分别为氧原子、硫原子、二甲基取代的亚甲基或者苯基取代的叔胺基中的一种；a与CL1-CL2键、CL2-CL3键、CL3-CL4键、CL‘1-CL’2键、CL‘2-CL’3键或CL‘3-CL’4键连接；
X、Y分别独立的表示为氧原子、硫原子、二甲基取代的亚甲基或者苯基取代的叔胺基中的一种。
所述R3、R4、R5分别独立的表示苯基、二苯胺基、吡啶基、二联苯基、三联苯基、蒽基、菲基、三嗪基、嘧啶基、喹啉基、二苯并呋喃基、9,9-二甲基芴基、9,9-二苯基芴基、咔唑基、苯并咔唑基、二苯并噻吩基、丫啶基、吲哚并咔唑基、吩噁嗪基或噻噁嗪基中的一种。
2.根据权利要求1所述的化合物，其特征在于所述化合物的结构为通式(7)、通式(8)、通式(9)或者通式(10)中的任一种：
3.根据权利要求1所述的化合物，其特征在于所述化合物的具体结构为：
中的任一种。
4.一种有机发光芳香化合物，其特征在于所述化合物的结构为：
中的任一种。
5.一种包含权利要求1～4任一项所述化合物的发光器件，其特征在于所述化合物作为发光层主体或者掺杂材料，用于制作有机电致发光器件。
6.一种制备权利要求1～4任一项所述化合物的方法，其特征在于制备过程中发生的反应方程式是：
具体的制备过程是：
称取Ar—Br和吖啶螺蒽酮，用甲苯溶解；再加入Pd2(dba)3、三叔丁基膦、叔丁醇钠；在惰性气氛下，将上述反应物的混合溶液于反应温度95～110℃，反应10～24小时，冷却并过滤反应溶液，滤液旋蒸，过硅胶柱，得到目标产物；所述Ar—Br与吖啶螺蒽酮的摩尔比为1:2.0～3.0，Pd2(dba)3与Ar—Br的摩尔比为0.006～0.02:1，三叔丁基膦与Ar—Br的摩尔比为0.006～0.02:1，叔丁醇钠与Ar—Br的摩尔比为1.0～3.0:1。
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101659638A (zh) * 2008-08-26 2010-03-03 财团法人工业技术研究院 有机化合物及包含其的有机电致发光装置
CN103650195A (zh) * 2011-07-15 2014-03-19 国立大学法人九州大学 有机电致发光元件及其所使用的化合物
TW201504392A (zh) * 2013-06-21 2015-02-01 Univ Kyushu Nat Univ Corp 紅色發光材料、有機發光元件及化合物
CN105340101A (zh) * 2013-07-03 2016-02-17 国立大学法人九州大学 发光材料、延迟萤光体、有机发光元件及化合物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101659638A (zh) * 2008-08-26 2010-03-03 财团法人工业技术研究院 有机化合物及包含其的有机电致发光装置
CN103650195A (zh) * 2011-07-15 2014-03-19 国立大学法人九州大学 有机电致发光元件及其所使用的化合物
TW201504392A (zh) * 2013-06-21 2015-02-01 Univ Kyushu Nat Univ Corp 紅色發光材料、有機發光元件及化合物
CN105340101A (zh) * 2013-07-03 2016-02-17 国立大学法人九州大学 发光材料、延迟萤光体、有机发光元件及化合物

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