CN111116628A - 一种有机化合物和使用该化合物的有机电致发光器件 - Google Patents

一种有机化合物和使用该化合物的有机电致发光器件 Download PDF

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CN111116628A
CN111116628A CN201911401825.3A CN201911401825A CN111116628A CN 111116628 A CN111116628 A CN 111116628A CN 201911401825 A CN201911401825 A CN 201911401825A CN 111116628 A CN111116628 A CN 111116628A
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electroluminescent device
organic electroluminescent
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赵晓宇
华万鸣
汪华月
高春吉
陈秋
黄娣
钱烨
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Zhejiang Huadisplay Optoelectronics Co Ltd
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Abstract

本发明公开了一种应用于有机电致发光领域的一种有机化合物和使用该化合物的有机电致发光器件，该有机化合物的分子结构式为结构式I所示结构：
Figure DDA0002347670990000011
其中，结构式I中，Ar1、Ar2、Ar3和Ar4独立地选自取代或未取代的C6‑C60的芳基或杂芳基，其中杂芳基含有选自B、N、O、S、Si及P中至少一个杂原子；X独立的选自O、S、Se、C(R)2、Si(R)2、NR、P(＝O)R或羰基，其中R选自H、CN、烷基、取代或未取代的C6‑C60的芳基或杂芳基；A独立地选自取代或未取代的下列结构：
Figure DDA0002347670990000012
其中，R1、R2选自H、C1‑C8的烷基。本发明一种有机化合物，具有较好的热稳定性，较高的三线态能级，能够平衡空穴和电子的传递，能量传递更加充分，能有效提高器件的效率和寿命。

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一种有机化合物和使用该化合物的有机电致发光器件
技术领域
本发明涉及有机电致发光领域的一种有机化合物和使用该化合物的有机电致发光器件，具体为三苯胺衍生物和使用该化合物的有机电致发光器件。
背景技术
有机电致发光器件(OLED:Organic Light Emission Diodes)有视角广阔、响应速度快、色彩质量高、可实现柔性发光等优点，具有广阔的应用前景。OLED器件通常是类三明治结构，包括正负电极膜层及夹在电极膜层之间的有机功能材料层。对OLED器件的电极施加电压，正电荷从正极注入，负电荷从负极注入，在电场作用下正负电荷在有机层中迁移相遇复合发光。已被广泛应用于新型照明灯具、智能手机及平板电脑等产品的显示面板，进一步还将向电视等大尺寸显示产品应用领域扩展，是一种发展快、技术要求高的新型显示技术。
一个效率好寿命长的有机电致发光器件通常是器件结构与各种有机材料的优化搭配的结果。常见的OLED器件通常包括以下种类的有机材料：空穴注入材料、空穴传输材料、电子传输材料，以及各色的发光材料(染料或者掺杂客体材料)和相应的主体材料等。
现在的磷光电致发光器件中大多采用主客体结构，即将磷光发射物质以一定的浓度掺杂在主体物质中，以避免三重态-三重态湮灭，提高磷光发射效率。作为现有的蓝光主体材料是基于蒽的稠环类衍生物，如专利CN1914293B、CN102448945B、US2015287928A1等所述，然而这些化合物存在发光效率和亮度不充分及器件寿命较差的问题。作为现有技术的发蓝光客体化合物，可采用的是芳基乙烯基胺类化合物(WO 04/013073,WO 04/016575,WO04/018587)。然而，这些化合物的热稳定性差，易分解，导致器件的寿命差，是目前产业上OLED材料最主要的缺点。此外，这些化合物的色纯度差，难以实现深蓝色的发光。另外，US7233019、KR 2006-0006760等专利公开了利用芳基胺取代基的芘系化合物的有机电致发光元件，但是因为蓝光的色纯度低，很难实现深蓝发光。
在磷光主体材料中，最常使用的是空穴传输型主体材料。这类材料的分子中含有电子给体，如咔唑和三苯胺结构，具有空穴传输的特点。三苯胺具有很高的三线态能级，ET为3.04eV，经常使用空的穴传输材料TAPC、TcTa、TPD等都是三苯胺的衍生物。大多数三苯胺的衍生物的HOMO能级要比咔唑衍生物高，大概为-5.3eV，而且它与ITO的功函数接近，HOMO也与空穴传输材料NPB接近，有利于空穴的注入，因此它们适合于做电致磷光主体材料。但是由于三苯胺分子结构是扭曲的，缺少刚性，使得三苯胺衍生物的热稳定性和形貌稳定性不够好，这影响了它们的实际应用。所以关于三苯胺衍生物作为磷光主体材料的报道不是很多。为了提高三苯胺的刚性结构，Yang课题组合成了桥联结构的三苯胺衍生物FATPA，[“Afully diarylmethylene-bridged triphenylamine derivativeas novel host forhighly efficient green phosphorescent OLEDs”,Org.Lett.2009,11,1503.]它是通过苯胺的邻位与二苯甲烷的亚甲基连接，三苯胺形成了接近平面的环状结构，这样的结构使得分子具有较高的玻璃转化温度，Tg为178℃。该分子同时保持了较高的三线态能级(ET＝2.78eV)和HOMO(-5.22eV)能级。
相对于红色磷光材料和绿色磷光材料，蓝色磷光材料是开发得最晚的，也是最不成熟的。这主要是由蓝色磷光波长短能级高，为了获得短波长发光，就必须拉大配体的能隙，即通过修配体的化学结构来拉大配体的HOMO和LUMO的能级，但是，这样又会导致配体和金属之间的配位键的减弱，一方面使得配合物的稳定性降低，配合物容易发生键断裂，而且会加速配合物以非辐射方式衰减会到基态，使磷光效率降低。因此，在蓝色磷光材料中，波长的蓝移和高效发光是一对矛盾，同时兼有两者是两难的选择。同时这也是器件的结构中起发光作用的磷光掺杂材料往往要搭配的主体材料使用的原因，但蓝色磷光材料的三线态能级比较高，所以常常需要比其三线态能级高的主体材料与之相匹配，这样才能保证将能量传递给客体蓝色磷光材料，释放出磷光。如果主体材料的三线态能级低于蓝色磷光材料的三线态能级，则能量会传递到主体材料上释放，而主体材料是纯的有机化合物，在室温下是看不到磷光的，所以器件的发光效率会降低。同时现有的蓝光材料存在热稳定性差，易分解，导致器件的寿命差；色纯度差，难以实现深蓝色的发光，因此在体现天然颜色的全彩色显示器方面有问题。因此，仍需进一步改进材料。高性能的蓝光材料一直是人们的开发重点。
本发明化合物不对称的结构特性提高器件效率，热稳定性、成膜等性能，本专利比较相对合成路线简单。本发明的有机化合物应用于OLED器件中的发光层，并当作蓝光材料使用，本发明化合物三苯胺与芴等连接起来三苯胺衍生物，由于螺环上的C原子阻断了三苯胺与其它苯环的共轭，使得分子的三线态得到了维持，具有较高的三线态能级，能量传递更加充分；电子和空穴的传递更加平衡，器件的效率和寿命更高。
发明内容
本发明为解决常用蓝色磷光材料的玻璃化温度较低，材料本身稳定性不高，且在高亮度下具有高效率滚降，阻碍其广泛使用的问题，而提供一种有机化合物、其合成方法及其在有机电致发光领域的应用。该有机化合物的分子结构如结构式I所示：
Figure BDA0002347670970000031
其中，结构式I中，Ar1、Ar2、Ar3和Ar4独立地选自取代或未取代的C6-C60的芳基或杂芳基，其中杂芳基含有选自B、N、O、S、Si及P中至少一个杂原子；X独立的选自O、S、Se、C(R)2、Si(R)2、NR、P(＝O)R或羰基，其中R选自H、CN、烷基、取代或未取代的C6-C60的芳基或杂芳基；A独立地选自取代或未取代的下列结构：
Figure BDA0002347670970000032
其中，R1、R2选自H、C1-C8的烷基。
优选的，本发明一种有机化合物独立地选自下列化合物：
Figure BDA0002347670970000041
Figure BDA0002347670970000051
Figure BDA0002347670970000061
本发明还提供了一种有机电致发光器件，该器件包括阴极层、阳极层和有机层，该有机层包括空穴注入层、空穴传输层、发光层、空穴阻挡层、电子注入层或电子传输层中至少一层，其中有机层中至少有一层含有如结构式I所表示的化合物。
其中，结构式I所表示的磷光一种有机化合物如前所述。
进一步的，结构式I所表示的一种有机化合物作为有机电致发光器件发光层的一种有机材料。
进一步的，结构式I所表示的一种有机化合物作为有机电致发光器件发光层的客体掺杂剂。
进一步的，如结构式I所表示的化合物可以单独使用在有机电致发光器件中，或和其他化合物混合使用；如结构式I所表示的化合物可以使用其中一种化合物，也可以同时使用结构式I中的两种或两种以上化合物；单独使用一种选自结构式I所述的化合物，或同时使用两种以上选自结构式I所述的化合物。
在本发明中，所述发光层可以为红色、黄色或蓝色发光层。在本发明中，所述发光层为蓝色发光层时，采用上述所述的有机电致器件用化合物作为蓝色主体或蓝色掺杂，可得到高效率、高分辨率、高亮度及长寿命的有机电致器件。
在本发明中，所述有机物层优选包括电子传输层，所述电子传输层包括上述技术方案所述的有机电致器件用化合物。在本发明中，所述电子传输层优选还包括金属化合物。
在本发明中，所述有机物层优选包括发光层和电子传输层，所述发光层和电子传输层均含有上述技术方案所述的有机电致器件用化合物，所述发光层和电子传输层中的有机化合物可以相同也可以不同。
本发明对所述有机电致器件的制备方法没有特殊的限制，除了使用式(I)的有机电致器件用化合物之外，采用本领域技术人员熟知的发光器件的制备方法和材料制备得到即可。
本发明所述的有机电致器件是有机光伏器件、有机发光器件(OLED)、有机太阳电池(OSC)、电子纸(e-paper)、有机感光体(OPC)、有机薄膜晶体管(OTFT)及有机内存器件(Organic Memory Element)中任意一种。
在本发明中，有机电致器件是可以利用喷溅涂覆法、电子束蒸发、真空蒸镀等方法在基板上蒸镀金属或具有导电性的氧化物以及它们的合金形成阳极；在制备得到的阳极表面按顺序蒸镀空穴注入层、空穴传输层、发光层、空气阻挡层和电子传输层，以后再蒸镀阴极的方法制备。以上方法以外基板上按阴极、有机物层、阳极顺序蒸镀制作有机电致器件。所述有机物层是也可以包括空穴注入层、空穴传输层、发光层、空穴阻挡层及电子传输层等多层结构。在本发明中有机物层是采用高分子材料按溶剂工程(旋转涂膜(spin-coating)、薄带成型(tape-casting)、刮片法(doctor-blading)、丝网印刷(Screen-Printing)、喷墨印刷或热成像(Thermal-Imaging)等)替代蒸镀方法制备，可以减少器件层数。
根据本发明的有机电致器件所使用的材料可以分为顶发射、低发射或双面发射。根据本发明实施方案的有机电致器件的化合物可以有机发光器件类似的原理适用于有机太阳能电池、照明的OLED、柔性OLED、有机感光体，有机薄膜晶体管等电致器件方面。
与现有技术相比，本发明的有益效果是：
本发明一种有机化合物合成方法简单，工艺步骤较少，产品分子量比较大，通过单键连接的多个共轭平面基团，空间对称性差，不易结晶分解，提高了材料的玻璃化温度，保证了材料长时间蒸镀不被分解；本发明的有机化合物应用于电致发光器件，具有较大的T1能够阻挡激子扩散，提高器件的效率和寿命；本发明的一种有机化合物能够平衡空穴和电子的传递，提高器件的寿命。
附图说明
图1为本发明的一种有机电致发光二极管器件结构层图；
其中，110代表基板，120表示阳极，130表示空穴注入层，140表示空穴传输层，150表示发光层，160表示空穴阻挡层，170表示电子传输层，180表示电子注入层，190表示阴极。
具体实施方式
为了使本发明的目的、技术方案及优点更加清楚明白，以下结合具体实施例，对本发明进行进一步详细说明。应当理解，此处所描述的具体实施例仅仅用以解释本发明，并不用于限定本发明。
合成例
1.中间体1-1制备：
Figure BDA0002347670970000081
在氮气氛围下，将3-溴-2-碘苯甲酸甲酯：10g、2-氯-5-甲氧基苯硼酸：4.6g、四(三苯基膦)钯(0)：0.5g、碳酸氢钠：5g、甲苯：100mL、乙醇：50ml、水：50ml投入烧瓶中，进行12小时的加热回流搅拌。冷却至室温(25℃)后，将反应溶液转移至分液漏斗中，用甲苯进行萃取。之后，将有机层用硫酸钠进行干燥，进行过滤、浓缩。将残渣用硅胶柱色谱进行纯化，得到了白色固体8.5g(产率89％)。根据LC-MS分析，该白色固体鉴定为中间体1-1。LC-MS：M/Z327.0(M+H)+。
2.中间体1-2制备：
Figure BDA0002347670970000091
在三口瓶中加入中间体1-1(7g)，四氢呋喃40毫升，0度低温滴加甲基溴化镁50毫升。升温至40度，反应2小时。滴加2M盐酸40毫升，氯化铵饱和溶液40毫升。加乙酸乙酯200毫升分离有机相，水洗(200毫升*3)三次，旋干备用。
3.中间体1-3制备：
Figure BDA0002347670970000092
在三口瓶中加入中间体1-2粗品(7g)，二氯乙烷60毫升，磷酸4g。升温至70度，反应过夜。LCMS监测反应，中间体转化完毕后，降温。加二氯甲烷(100毫升)，水洗(200毫升*3)三次后，加甲苯旋干有机相，拌硅胶过柱，得纯品5g。根据LC-MS分析，该白色固体鉴定为中间体2-3。LC-MS：M/Z309.0(M+H)+。
4.中间体1-4的制备
中间体1-4-1制备：
Figure BDA0002347670970000093
在氮气氛围下，将中间体1-3：2.0g、2,2'-联苯二硼酸：1.57g、四(三苯基膦)钯(0)：0.2g、碳酸氢钠：2g、甲苯：20mL、乙醇：10ml、水：10ml投入烧瓶中，进行12小时的加热回流搅拌。冷却至室温(25℃)后，将反应溶液转移至分液漏斗中，用甲苯进行萃取。之后，将有机层用硫酸钠进行干燥，进行过滤、浓缩。将残渣用硅胶柱色谱进行纯化，得到了白色固体1.8g(产率80％)。根据LC-MS分析，该白色固体鉴定为中间体1-4-1。LC-MS：M/Z345.2(M+H)+。
中间体1-4-2制备：
Figure BDA0002347670970000101
在氮气氛围下，将中间体1-3：2g、1,8-二苯硼酸：1.5g、四(三苯基膦)钯(0)：0.2g、碳酸氢钠：2g、甲苯：20mL、乙醇：10ml、水：10ml投入烧瓶中，进行12小时的加热回流搅拌。冷却至室温(25℃)后，将反应溶液转移至分液漏斗中，用甲苯进行萃取。之后，将有机层用硫酸钠进行干燥，进行过滤、浓缩。将残渣用硅胶柱色谱进行纯化，得到了白色固体1.7g(产率82％)。根据LC-MS分析，该白色固体鉴定为中间体1-4-2。LC-MS：M/Z319.1(M+H)+。
5.中间体1-5的制备
中间体1-5-1的制备
Figure BDA0002347670970000102
在1L圆底烧瓶中加入1-4-1(6.3g,19.1mmol)、二氯甲烷180mL并常温搅拌。将溴(3.4mL,66mmol)稀释滴加到二氯甲烷50mL，常温下搅拌8小时，反应完毕后在反应容器中国投入丙酮100mL并搅拌。将生成的固体过滤之后利用丙酮进行清洗。用一氯苯重结晶固体而获得中间体1-5-1(6.2g,收率，67.5％)。LC-MS：M/Z503.0(M+H)+。
中间体1-5-2的制备
Figure BDA0002347670970000111
在1L圆底烧瓶中加入1-4-2(6.3g,19.1mmol)、二氯甲烷180mL并常温搅拌。将溴(3.4mL,66mmol)稀释滴加到二氯甲烷50mL，常温下搅拌8小时，反应完毕后在反应容器中国投入丙酮100mL并搅拌。将生成的固体过滤之后利用丙酮进行清洗。用一氯苯重结晶固体而获得中间体1-5-2(7.2g,收率，75％)。LC-MS：M/Z477.1(M+H)+。
6.中间体2-1的合成
Figure BDA0002347670970000112
在氮气氛围下，将1，2-二氯-3-硝基苯：20g、2-甲氧基苯硼酸：15g、四(三苯基膦)钯：1g、碳酸氢钠：20g、甲苯：160mL、乙醇：80ml、水：80ml投入烧瓶中，进行12小时的加热回流搅拌。冷却至室温(25℃)后，将反应溶液转移至分液漏斗中，用甲苯进行萃取。之后，将有机层用硫酸钠进行干燥，进行过滤、浓缩。将残渣用硅胶柱色谱进行纯化，得到了白色固体23g(产率83％)。根据LC-MS分析，该白色固体鉴定为中间体2-1。LC-MS：M/Z264.0(M+H)+。
7.中间体2-2的合成:
Figure BDA0002347670970000113
在氮气氛围下，将中间体2-1：20g、磷酸三乙酯：200mL投入烧瓶中，进行12小时的回流搅拌。冷却至室温(25℃)后，将反应溶液蒸馏进行纯化，得到了白色固体13g(产率74％)。根据LC-MS分析，该白色固体鉴定为中间体2-2。LC-MS：M/Z232.0(M+H)+。
8.中间体2-3的制备：
Figure BDA0002347670970000121
将中间体2-2：10g、醋酸：100mL、氢溴酸：20mL投入烧瓶中，进行12小时的搅拌。将反应溶液乙酸乙酯萃取后蒸干溶剂，得到了粗品10g，直接投入下一步反应。根据LC-MS分析，该白色固体鉴定为中间体2-3。LC-MS：M/Z218.0(M+H)+。
9.中间体2-4的制备：
Figure BDA0002347670970000122
将中间体2-3：10g、三氟甲磺酸酐：11g、三乙胺：6g、二氯甲烷：100mL投入烧瓶中，进行12小时的搅拌。萃取后，过柱纯化得到白色固体8g。根据LC-MS分析，该白色固体鉴定为中间体2-4。LC-MS：M/Z349.9(M+H)+。
10.中间体2-5的制备
中间体2-5-1的制备：
Figure BDA0002347670970000123
在氮气氛围下，将中间体2-4：5g、2,2'-联苯二硼酸：3.5g、四(三苯基膦)钯(0)：0.5g、碳酸氢钠：5g、甲苯：50mL、乙醇：25ml、水：25ml投入烧瓶中，进行12小时的加热回流搅拌。冷却至室温(25℃)后，将反应溶液转移至分液漏斗中，用甲苯进行萃取。之后，将有机层用硫酸钠进行干燥，进行过滤、浓缩。将残渣用硅胶柱色谱进行纯化，得到了白色固体1.1g(产率26％)。根据LC-MS分析，该白色固体鉴定为中间体2-5-1。LC-MS：M/Z318.1(M+H)+。
中间体2-5-2制备：
Figure BDA0002347670970000131
在氮气氛围下，将中间体2-4：2g、1,8-二奈硼酸：1.5g、四(三苯基膦)钯(0)：0.2g、碳酸氢钠：2g、甲苯：20mL、乙醇：10ml、水：10ml投入烧瓶中，进行12小时的加热回流搅拌。冷却至室温(25℃)后，将反应溶液转移至分液漏斗中，用甲苯进行萃取。之后，将有机层用硫酸钠进行干燥，进行过滤、浓缩。将残渣用硅胶柱色谱进行纯化，得到了白色固体0.4g(产率24％)。根据LC-MS分析，该白色固体鉴定为中间体2-5-2。LC-MS：M/Z292.1(M+H)+。
实施例1
化合物C-6的合成
Figure BDA0002347670970000132
在250mL圆底烧瓶中加入中间体1-5-1(2.2g,4.38mmol)、二(4-甲基苯基)胺(1.9g,9.64mol)、Pd2(dba)3(0.04g,0.2mmol)、叔丁醇钠(1.7g,0.0175mol)、三叔丁基膦(0.035g,0.2mmol)、甲苯60mL，并回流搅拌2小时。在反应完毕之后常温冷却。利用二氯甲烷和水对反应溶液进行萃取。分离有机层，并用硫酸镁进行干燥，然后减压浓缩。利用柱层析法对物质进行分离提纯，后利用二氯甲烷和丙酮进行重结晶而获得化合物C-6(1.5g,47％)。生成的化合物通过用LC-MS确定。LC-MS:M/Z735.4(M+H)+。理论元素含量(％)C55H46N2：C,89.88；H,6.31；N,3.81。上述结果证实获得产物为目标产品。
11.中间体2-6的制备
中间体2-6-1的制备
Figure BDA0002347670970000141
中间体2-6-1的合成步骤如上述反应式，制备及确认方法同化合物C-6，可获得中间体2-6-1(2.0g,44.9％)。LC-MS：M/Z394.2(M+H)+。
中间体2-6-2的制备
Figure BDA0002347670970000142
中间体2-6-2的合成步骤如上述反应式，制备及确认方法同化合物C-6，可获得化合物中间体2-6-2(1.9g,45.9％)。LC-MS：M/Z368.1(M+H)+。
12.中间体2-7的制备
中间体2-7-1的制备
Figure BDA0002347670970000143
中间体2-7-1的合成步骤如上述反应式，制备及确认方法同中间体1-5-1，可获得中间体2-7-1。LC-MS：M/Z552.0(M+H)+。
中间体2-7-2的制备
Figure BDA0002347670970000144
中间体2-7-2的合成步骤如上述反应式，制备及确认方法同中间体1-5-2，可获得化合物中间体2-7-2。LC-MS：M/Z526.0(M+H)+。
实施例2
化合物C-9的合成
Figure BDA0002347670970000151
化合物C-9的合成步骤如上述反应式，制备及确认方法同化合物C-6，可获得化合物C-9(1.9g,45.9％)。LC-MS：M/Z943.4(M+H)+。
实施例3
化合物C-11的合成
Figure BDA0002347670970000152
化合物C-11的合成步骤如上述反应式，制备及确认方法同化合物C-6，可获得化合物C-11(2.1g,48.7％)。LC-MS：M/Z983.4(M+H)+。
实施例4
化合物C-20的合成
Figure BDA0002347670970000153
化合物C-20的合成步骤如上述反应式，制备及确认方法同化合物C-6，可获得化合物C-20(1.6g,49.2％)。LC-MS：M/Z743.3(M+H)+。
实施例5
化合物C-28的合成
Figure BDA0002347670970000161
化合物C-28的合成步骤如上述反应式，制备及确认方法同化合物C-6，可获得化合物C-28(2.2g,55.1％)。LC-MS：M/Z911.4(M+H)+。
实施例6
化合物C-38的合成
Figure BDA0002347670970000162
化合物C-38的合成步骤如上述反应式，制备及确认方法同化合物C-6，可获得化合物C-38(1.6g,46.9％)。LC-MS：M/Z779.3(M+H)+。
实施例7
化合物C-5的合成
Figure BDA0002347670970000163
化合物C-5的合成步骤如上述反应式，制备及确认方法同化合物C-6，可获得化合物C-5(1.6g,50.9％)。LC-MS：M/Z681.3(M+H)+。
实施例8
化合物44的合成
Figure BDA0002347670970000171
化合物C-44的合成步骤如上述反应式，制备及确认方法同化合物C-6，可获得化合物C-44(2.6g,51.9％)。LC-MS：M/Z784.3(M+H)+。
实施例9
化合物47的合成
Figure BDA0002347670970000172
化合物C-47的合成步骤如上述反应式，制备及确认方法同化合物C-6，可获得化合物C-47(1.8g,50.9％)。LC-MS：M/Z758.4(M+H)+。
本发明还通过热蒸镀的方式制备了10个底发光器件(各个具体的器件结构如下：
器件实施例：
将费希尔公司涂层厚度为
Figure BDA0002347670970000175
的ITO玻璃基板放在蒸馏水中清洗2次，超声波洗涤30分钟，再用蒸馏水反复清洗2次，超声波洗涤10分钟，蒸馏水清洗结束后，采用异丙醇、丙酮、甲醇溶剂按顺序进行超声波洗涤后干燥，将干燥后的基板转移到等离子体清洗机里，将上述基板洗涤5分钟后送到蒸镀机里。
在已经清洗好的ITO透明电极上依次蒸镀空穴注入层2-TNATA蒸镀厚度为
Figure BDA0002347670970000173
空穴传输层a-NPD蒸镀厚度为
Figure BDA0002347670970000174
ADN(9,10-二(2-萘基)蒽)和5％的BD1～BD3或本发明一种有机化合物蒸镀厚度为
Figure BDA0002347670970000181
空穴阻挡层及电子传输层TPBi蒸镀厚度为
Figure BDA0002347670970000182
LiF蒸镀厚度为
Figure BDA0002347670970000183
和Al蒸镀厚度为
Figure BDA0002347670970000184
形成阴极；上述过程有机物蒸镀速度保持
Figure BDA0002347670970000185
/sec，LiF的蒸镀速度为
Figure BDA0002347670970000186
Al的蒸镀速度为
Figure BDA0002347670970000187
Figure BDA0002347670970000188
表1为本发明实施例和比较例制备得到的有机发光器件的性能检测结果。
[表1]
Figure BDA0002347670970000189
从上述表1结果中，采用本发明提供的有机电致器件用化合物制备有机电致器件，有机电致器件的发光效率和寿命特性显著提高。
以上所述，仅为本发明较佳的具体实施方式，但本发明的保护范围并不局限于此，任何熟悉本技术领域的技术人员在本发明揭露的技术范围内，根据本发明的技术方案及其发明构思加以等同替换或改变，都应涵盖在本发明的保护范围之内。

Claims (7)

1.一种应用于有机电致发光领域的有机化合物，该有机化合物的分子结构式为结构式I所示结构；
Figure FDA0002347670960000011
其中，结构式I中，Ar1、Ar2、Ar3和Ar4独立地选自取代或未取代的C6-C60的芳基或杂芳基，其中杂芳基含有选自B、N、O、S、Si及P中至少一个杂原子；X独立的选自O、S、Se、C(R)2、Si(R)2、NR、P(＝O)R或羰基，其中R选自H、CN、烷基、取代或未取代的C6-C60的芳基或杂芳基；A独立地选自取代或未取代的下列结构：
Figure FDA0002347670960000012
其中，R1、R2选自H、C1-C8的烷基。
2.根据权利要求1所述的一种应用于有机电致发光领域的有机化合物，其特征在于：所述有机化合物独立地选自下列化合物：
Figure FDA0002347670960000013
Figure FDA0002347670960000021
Figure FDA0002347670960000031
Figure FDA0002347670960000041
3.一种有机电致发光器件，包括阴极层、阳极层和有机层，该有机层包括空穴注入层、空穴传输层、发光层、空穴阻挡层、电子注入层、电子传输层中的至少一层，其特征在于：该器件的有机层中至少有一层含有如权利要求1所述的有机化合物。
4.根据权利要求3所述的有机电致发光器件，其特征在于，有机电致发光器件发光层中含有权利要求1所述的化合物。
5.根据权利要求3或权利要求4所述的有机电致发光器件，其特征在于，权利要求1所述的化合物在有机电致发光器件发光层中作为客体掺杂剂使用。
6.根据权利要求3所述的有机电致发光器件，其特征在于，权利要求1所述的化合物可以单独使用，或和其他化合物混合使用。
7.根据权利要求3所述的有机电致发光器件，其特征在于，单独使用一种选自如权利要求2所述的有机化合物，或同时使用两种或两种以上选自如权利要求2所述有机化合物。
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CN112062774A (zh) * 2020-09-09 2020-12-11 浙江华显光电科技有限公司 一种有机化合物和使用该化合物的有机电致发光器件
CN112979536A (zh) * 2021-03-12 2021-06-18 吉林奥来德光电材料股份有限公司 一种磷光主体材料及其制备方法和有机电致发光器件
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CN112062774A (zh) * 2020-09-09 2020-12-11 浙江华显光电科技有限公司 一种有机化合物和使用该化合物的有机电致发光器件
WO2022088910A1 (zh) * 2020-11-02 2022-05-05 北京八亿时空液晶科技股份有限公司 一种咔唑衍生物及其应用
CN112979536A (zh) * 2021-03-12 2021-06-18 吉林奥来德光电材料股份有限公司 一种磷光主体材料及其制备方法和有机电致发光器件
CN116836107A (zh) * 2023-07-05 2023-10-03 西安欧得光电材料有限公司 一种咔唑并八元环大共轭结构oled材料及制备方法
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