CN109678731B - 有机化合物、有机电致发光材料、电子设备 - Google Patents

有机化合物、有机电致发光材料、电子设备 Download PDF

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CN109678731B
CN109678731B CN201910094666.0A CN201910094666A CN109678731B CN 109678731 B CN109678731 B CN 109678731B CN 201910094666 A CN201910094666 A CN 201910094666A CN 109678731 B CN109678731 B CN 109678731B
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organic electroluminescent
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CN109678731A (zh
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曹建华
邵哲
郭剑
隋岩
纪秦思
董梁
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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Abstract

涉及有机化合物、包含该有机化合物的有机电致发光元件、电子设备，所述有机化合物为下述的式I所示化合物。
Figure DDA0001964204910000011

Description

有机化合物、有机电致发光材料、电子设备
技术领域
本发明涉及有机电致发光技术领域。更具体地，涉及有机化合物和包含该化合物的有机电致发光元件、有机电致发光元件。
背景技术
有机电致发光元件所使用的物质大部分为纯有机物或有机物与金属形成络合物的有机金属络合物，根据用途可区分为空穴注入物、空穴输送物、发光物、电子输送物、电子注入物等。作为空穴注入物或空穴输送物主要使用离子化能相对较小的有机物，作为电子注入物或电子输送物主要使用电负性较大的有机物。此外，作为发光辅助层所使用的物质最好能满足如下特性。
第一、有机电致发光元件中所使用的物质需较好的热稳定性，其原因是在有机电致发光元件内部因电荷的迁移而发生焦耳热，目前，作为空穴输送层通常所使用的材料的玻璃化温度低，因此在低温下驱动时出现因发生结晶化而引起发光效率降低的现象。第二、为了降低驱动电压，需要与阴极和阳极邻接的有机物设计成电荷注入势垒较小，电荷迁移率高。第三、电极和有机层的界面、有机层和有机层的界面上一直存在能量壁垒而不可避免地累积一些电荷，因此需要使用电化学稳定性优异的物质。
发光层由主发光体和掺杂物这两种物质构成，掺杂物需要量子效率高，与掺杂物相比主发光体需要能隙大而容易发生向掺杂物的能量转移。用于电视、移动设备等的显示器根据红色、绿色、蓝色这三色实现全彩色，发光层分别由红色主发光体/掺杂物、绿色主发光体/掺杂物以及蓝色主发光体/掺杂物构成。目前为止，蓝色发光层与其它层的颜色相比，寿命、效率以及色纯度等方面处于很大的劣势。
用作蓝色掺杂物的蒽、芘、氧杂萘邻酮等，这些荧光性物质还用于光触媒、半导体、电荷输送领域、结晶学领域、碳纳米管、荧光探针、树枝状分子等各种领域。利用芘类化合物的蓝色发光有机电致发光元件记载在美国专利第723301号、韩国公开专利第20030054519号、第20060006760号、第20077005909号、第20090071884号等，但是仍需要开发具有高量子效率的同时可显示深蓝色的发光材料。尤其是，目前为了使R、G、B三像素采用喷墨、打印等方式的溶液制程工序，因此迫切需要溶解度优异的物质的开发。
发明内容
为了解决现有技术中存在的至少一个问题，本发明人等进行了深入研究，发现本发明的在芘分子内部导入有两个环状烷基从而减弱分子间的π-π相互作用、获得了分子空间位阻增大、稳定性和在有机溶媒中的溶解性提高了的新型的化合物，从而完成了本发明。
本发明的目的在于提供一种新型的有机化合物，该有机化合物在低温下也可以进行升华、蒸镀以及进行溶液工序，并且具有与以往的化合物相比短的最大发光波长。
本发明的另一目的还在于提供含有本发明的有机化合物的有机电致发光元件。
本发明的再一目的还在于提供含有本发明的有机化合物的电子设备。
本发明的有机化合物由于具有前述的在芘分子内部导入有两个环状烷基这样的式I所示的结构，能够阻碍有机分子的激态分子的生成、增加内部电子密度和稳定性，由此能够提高使用该有机化合物的电致发光元件的效率、寿命。
另外，本发明的有机化合物由于在有机溶媒中的溶解度提高从而提高了蓝光掺杂工序的生产效率，因此解决了以往蓝光掺杂物所需工序的生产效率低以及费用高的问题，并且，使用本发明的有机化合物，不需要以往的蒸镀工序而是在溶液工序中就可以制造元件。
为达到上述目的，本发明提供一种有机化合物，其为式I所示的化合物：
Figure GDA0003307705160000021
其中，R1、R2、R3、R4、R5、R6各自独立地选自氢原子、氘原子、卤原子、硝基、氰基、任选具有取代基的碳原子数为1～30的链烷基、任选具有取代基的碳原子数为3～30的环烷基、任选具有取代基的碳原子数为1～30的烷氧基、任选具有取代基的碳原子数为2～30的烯基、任选具有取代基的碳原子数为2～30的炔基、任选具有取代基的碳原子数为2～30的杂烷基、任选具有取代基的碳原子数为7～30的芳烷基、任选具有取代基的碳原子数为6～60的芳基、任选具有取代基的碳原子数为6～60的杂芳基、任选具有取代基的碳原子数为6～60的杂芳基烷基、任选具有取代基的碳原子数为6～60的芳氧基组成的组；所述取代基分别独立地选自氢原子、氘原子、卤原子、羟基、氰基、硝基、羧基、羧酸酯基、碳原子数为1～30的链烷基、碳原子数为3～30的环烷基、碳原子数为1～30的杂烷基、碳原子数为2～30的烯基、碳原子数为2～30的炔基、碳原子数为1～30的烷氧基、碳原子数为7～30的芳烷基、碳原子数为6～30的芳基、碳原子数为2～30的杂芳基、碳原子数为3～30的杂芳烷基、碳原子数为1～30的烷基氨基、碳原子数为6～30的芳基氨基、碳原子数为6～30的芳烷基氨基、碳原子数为2～30的杂芳基氨基、碳原子数为6～30的芳氧基组成的组；
环L1为包含C1、C2、C3的碳原子数为4～7的饱和或不饱和的环，环L2为包含C4、C5、C6的碳原子数为4～7的饱和或不饱和的环。
另外，本发明还提供一种有机电致发光元件，其含有本发明的式I所示的有机化合物。
另外，本发明还提供一种有机电致发光元件，所述有机电致发光元件包括第一电极、第二电极和置于所述第一电极、第二电极之间的至少一层包含本发明的式I所示的有机化合物的有机层。
另外，本发明还提供一种电子设备，其含有本发明的有机电致发光元件。
本发明还提供上述有机化合物在制备有机电致发光元件中的应用。
本发明还提供上述有机化合物在制备电子设备中的应用。
本发明的式I所示的有机化合物可以作为蓝色掺杂物，与己知的蓝色掺杂物相比，发光波长蓝移5nm以上，由此可提供适用于有机电致发光元件的深蓝色的蓝色主发光体/掺杂体系。
本发明的有机化合物在芘分子核心导入有两个环烷基，由此能够阻断掺杂物的激发态复合物的生成，增加分子内部的密度和掺杂物的稳定性，增加元件的效率和寿命。
另外，本发明的式I所示的有机化合物由于两个环烷基的引入，从而对有机溶媒更具有优异的溶解度，具有在溶液工序中容易制造有机电致发光元件的特性，减少生产工艺费用。
附图说明
图1示出本发明实施例11中的OLED元件结构示意图，其中，1-基板、2-阳极层、3-空穴注入层、4-空穴传输层、5-电子阻挡层、6-有机发光层、7-空穴阻挡层、8-电子传输层、9-阴极层。
图2示出本发明实施例10中化合物SLC-B191的荧光发射图谱。
具体实施方式
[有机化合物]
本发明的式I所示的化合物优选为下述的式II所示的有机化合物：
Figure GDA0003307705160000041
其中，R1、R2、R3、R4、R5、R6各自独立地选自氢原子、氘原子、卤原子、硝基、氰基、任选具有取代基的碳原子数为1～30的链烷基、任选具有取代基的碳原子数为3～30的环烷基、任选具有取代基的碳原子数为1～30的烷氧基、任选具有取代基的碳原子数为2～30的烯基、任选具有取代基的碳原子数为2～30的炔基、任选具有取代基的碳原子数为2～30的杂烷基、任选具有取代基的碳原子数为7～30的芳烷基、任选具有取代基的碳原子数为6～60的芳基、任选具有取代基的碳原子数为6～60的杂芳基、任选具有取代基的碳原子数为6～60的杂芳基烷基、任选具有取代基的碳原子数为6～60的芳氧基组成的组；所述取代基分别独立地选自氢原子、氘原子、卤原子、羟基、氰基、硝基、羧基、羧酸酯基、碳原子数为1～30的链烷基、碳原子数为3～30的环烷基、碳原子数为1～30的杂烷基、碳原子数为2～30的烯基、碳原子数为2～30的炔基、碳原子数为1～30的烷氧基、碳原子数为7～30的芳烷基、碳原子数为6～30的芳基、碳原子数为2～30的杂芳基、碳原子数为3～30的杂芳烷基、碳原子数为1～30的烷基氨基、碳原子数为6～30的芳基氨基、碳原子数为6～30的芳烷基氨基、碳原子数为2～30的杂芳基氨基、碳原子数为6～30的芳氧基组成的组；
n各自独立地表示1～3的整数；
R7、R8各自独立地选自氢原子、任选具有取代基的碳原子数为1～30的链烷基、任选具有取代基的碳原子数为3～30的环烷基、任选具有取代基的碳原子数为1～30的烷氧基、卤原子、氰基、任选具有取代基的碳原子数为1～30的杂烷基；R7、R8的取代基各自独立地选自氘原子、羧基、氰基、卤原子、硝基、羟基、羧酸酯基、碳原子数为1～30的链烷基、碳原子数为2～30的烯基、碳原子数为2～30的炔基、碳原子数为1～30的环烷基、碳原子数为1～30的杂烷基组成的组。
进一步，本发明的式I所示的化合物优选选自以下的化合物：
Figure GDA0003307705160000051
Figure GDA0003307705160000061
Figure GDA0003307705160000071
Figure GDA0003307705160000081
Figure GDA0003307705160000091
Figure GDA0003307705160000101
Figure GDA0003307705160000111
Figure GDA0003307705160000121
Figure GDA0003307705160000131
Figure GDA0003307705160000141
Figure GDA0003307705160000151
Figure GDA0003307705160000161
Figure GDA0003307705160000171
Figure GDA0003307705160000181
Figure GDA0003307705160000191
[有机电致发光材料]
本发明的有机电致发光材料中包含本发明的式I所示的有机化合物中的一种或多种。本发明的有机电致发光材料可以仅由本发明的有机化合物的一种或多种形成，也可以含有本发明的有机化合物之外的其他材料。
通过在本发明的有机电致发光材料中含有本发明的有机化合物，能够获得适用于有机电致发光元件的深蓝色的蓝色主发光体/掺杂体系的发光效率高的有机电致发光材料。
另外，由于所含有的本发明的式I所示的有机化合物的两个环烷基的引入，从而对有机溶媒更具有优异的溶解度，因此，能够通过溶液工序容易地制造有机电致发光元件，不需采用蒸镀工艺，能够减少生产工艺费用。
[有机电致发光元件]
本发明的有机电致发光元件包括第一电极、第二电极和置于所述第一电极、第二电极之间的至少一层的含有本发明的式I所示的有机化合物的有机发光层。前述的有机发光层中除了含有本发明的有机化合物之外，还可以含有用于形成该层的其他材料，可包括通常添加的物质，例如公知的掺杂物以及主发光体。
对于有机电致发光元件的其他构成，没有特别的限定。在有机电子发光装置的一个实施方式中，例如，前述的第一电极、第二电极之间还可以具有例如一层或多层的选自电子注入层、电子输送层、空穴阻挡层、电子阻挡层、空穴输送层、空穴注入层的层。
在有机电致发光元件的一个实施方式中，前述的有机发光层可以包含例如作为主发光体的选自萘、蒽、芘、苝、菲、荧蒽、
Figure GDA0003307705160000201
苯并蒽、并五苯以及它们的衍生物中的一种以上，以及作为掺杂物的一种以上的本发明的有机化合物。
本发明的有机电致发光元件中，前述有机发光层中包含的本发明的有机化合物可以是掺杂于主体材料中发光的材料，也可以是非掺杂发光的材料。具体地，有机发光层中可采用小分子材料作为主体材料进一步掺杂荧光材料或磷光染料。前述的有机发光层的材料中可以包括本发明的有机化合物作为磷光掺杂材料在相应的主体材料中发光。
本发明的有机电致发光元件中，作为含有本发明的有机化合物的层之外的层的构成，没有任何限定，本领域技术人员能够根据本领域的技术常识根据需要来决定有机电致发光元件的其他层的构成。
作为本发明的有机电致发光元件的一个具体的例子，参照图1进行说明。图1是本发明的一个实施方式的有机电致发光元件的结构示意图。图1中，在基板1上依次有阳极层2、空穴注入层3、空穴传输层4、电子阻挡层5、有机发光层6、空穴阻挡层7、电子传输层8、阴极层9。在前述的有机发光层6中含有本发明的金属配合物。当本发明的有机电致发光元件在与外接电源连接而被施加电压时，有机发光层6中的有机化合物产生电致发光。
作为本发明的有机电致发光元件的制备方法，可以列举出下述的制备方法，但是并不限于此，本领域技术人员能够根据本领域的技术常识进行各种改变。前述的制备方法包括以下工序：
清洗工序：使用清洗剂、去离子水、有机溶剂等清洗带有ITO的玻璃基片；
形成空穴注入层的工序：通过真空蒸镀在前述的阳极层上蒸镀含有本发明的金属配合物的空穴注入层形成材料，从而在前述基板上形成包含本发明的金属配合物的空穴注入层；
形成空穴传输层的工序：通过真空蒸镀在前述的空穴注入层上形成空穴传输层；
形成有机发光层的工序：在前述的空穴传输层上通过真空蒸镀包含本发明材料的有机发光层形成材料从而在前述空穴传输层上形成含有本发明的金属配合物的有机发光层；
形成电子传输层的工序：在前述有机发光层上通过真空蒸镀包含本发明的金属配合物的电子传输层形成材料，从而在前述有机发光层上形成含有本发明的金属配合物的电子传输层；
形成阴极层的工序：在前述电子传输层上蒸镀、溅射或者旋涂阴极形成材料从而形成阴极层。
[电子设备]
本发明的电子设备含有本发明的有机电致发光元件。对于本发明的电子设备的其他构成，没有特别的限定。
实施例
为了更清楚地说明本发明，下面结合优选实施例和附图对本发明做进一步的说明。本领域技术人员应当理解，下面所具体描述的内容是说明性的而非限制性的，不应以此限制本发明的保护范围。
本发明中，制备方法如无特殊说明则均为常规方法。所用的原料如无特别说明均可从公开的商业途径获得，所述百分比如无特殊说明均为质量百分比。本发明提供的一系列新型有机化合物，所有的反应都是在众所周知的适合条件下进行，有些涉及到简单的有机制备，例如苯硼酸衍生物的制备均能通过熟练的操作技能合成，在本发明中没有详细描述。
下面例示出属于本发明的式I所示化合物的部分化合物的合成路线。本领域技术人员应当理解是，其他的式I所示的化合物的合成路线也可以参照下述的合成路线来进行。
Figure GDA0003307705160000221
上述反应路线举例给出了化合物式I的合成路线，制备了关键中间体I.-1、I.-2、I.-3、I.-4、I.-5和I.-6系列化合物。其中R1、R2、R3、R4、R5、R6、R7、R8和n与前述定义相同。
在本发明实施例中使用了以下缩写：
表1缩写与全称
缩写 全称
THF 四氢呋喃
n-BuLi 正丁基锂
Pd(PPh<sub>3</sub>)<sub>2</sub>Cl<sub>2</sub> 双(三苯基磷)氯化钯
(PinB)<sub>2</sub> 联硼酸频那醇酯
Pd(PPh<sub>3</sub>)<sub>4</sub> 四(三苯基磷)钯
NBS N-溴代琥珀酰亚胺
Pd<sub>2</sub>(dba)<sub>3</sub> 三(二亚苄基丙酮)二钯
实施例1
化合物SLC-B01的制备：
化合物SLC-B01的制备方法，包括如下步骤：
第一步：化合物Int-1的制备
Figure GDA0003307705160000231
20.0g(70.6mmol)的邻溴碘苯(CAS:583-55-1)溶解在200ml苯中，加入103ml的二异丙基胺，在氮气保护下，加入1.4g(7.0mmol)的碘化亚铜和2.5g(3.5mmol)的Pd(PPh3)2Cl2催化剂，再加入8.4g(77.6mmol)的2-甲基-3,5-己二炔-2-醇(CAS:763-12-2)，室温搅拌反应12小时后，加入200ml的冰水稀释，分出有机相，水相用乙酸乙酯萃取，有机相用无水硫酸钠干燥，过滤，减压浓缩干，用硅胶柱分离纯化，得17.8g的黄色固体，收率96％。
第二步：化合物Int-2的制备
Figure GDA0003307705160000232
取15.0g(57.0mmol)第一步制备的中间体Int-1用150ml的无水THF溶解，氮气保护下，冰水浴降温至0℃，分批加入2.5g(62.7mmol，60％)的氢化钠固体，搅拌反应30分钟，用液氮降温至-78℃，滴加入27.5ml的2.5M正丁基锂正己烷溶液，搅拌反应30分钟，滴加入8.5ml的硼酸三甲酯，升到室温搅拌反应1小时，加入50ml的3M稀盐酸水溶液，搅拌反应30分钟，分出有机相，水相用乙酸乙酯萃取，干燥，过滤，滤液减压浓缩干，加入50ml的石油醚分散，过滤，干燥，得11.3g的黄色固体，收率87％。
第三步：化合物Int-3的制备
Figure GDA0003307705160000233
将第二步得到的10.0g(43.8mmol)化合物Int-2和第一步得到的10.5g(40.0mmol)化合物Int-1、10.0g的无水碳酸钠、80ml甲苯和40ml的乙醇以及40ml的水混合，再加入80mg的催化剂Pd(PPh3)4，在氮气保护下，升温回流反应12小时，冷却到室温，分出有机相，水相用乙酸乙酯萃取，有机相干燥，过滤，滤液减压浓缩干，残余物用硅胶柱分离纯化，得13.3g的Int-3，黄色结晶物，收率91％。
第四步：化合物Int-4的制备
Figure GDA0003307705160000241
取10.0g(27.2mmol)第三步的中间体Int-3用200ml干燥的甲苯溶解、加入0.4g(1.5mmol)的二氯化铂，在氮气保护下，升温至100℃，搅拌反应24小时，冷却到室温，减压浓缩干，用硅胶柱分离纯化，得到7.4g的Int-4，黄色结晶物，收率74％。
第五步：化合物Int-5的制备
Figure GDA0003307705160000242
将第四步制备的7.0g(19.0mmol)化合物Int-4溶解在200ml的乙酸乙酯中，加入0.7g的10％无水钯/碳，用氢气置换三次，室温下通入氢气至0.3MPa，搅拌反应24小时，过滤，滤液减压浓缩干，残余物用硅胶柱分离纯化，得6.2g的Int-5，黄色油状物，收率86％。
第六步：化合物Int-6的制备
Figure GDA0003307705160000243
将第五步制备的6.0g(19.0mmol)化合物Int-5溶解在60ml的甲苯中，加入1.2g的甲基磺酸，升温回流反应，利用分水器在回流状态下分出生成的水，反应结束后，加入50ml的水，分出有机相，水相用甲苯萃取，收集有机相，干燥，过滤，滤液减压浓缩干，用硅胶柱分离纯化，得到3.5g的Int-6，白色固体，收率65％。
第七步：化合物Int-7的制备
Figure GDA0003307705160000251
将第六步制备的5.0g(14.7mmol)化合物Int-6溶解在120ml的氯仿中，加入5.8g(32.4mmol)的NBS，室温搅拌反应12小时，反应结束后，加入50ml的饱和亚硫酸氢钠水溶液，分出有机相，有机相用水洗三次，收集有机相，干燥，过滤，滤液减压浓缩干，用硅胶柱分离纯化，得到4.4g的Int-7，白色固体，收率60％。
第八步：化合物SLC-B01的制备
Figure GDA0003307705160000252
将第七步制备的3.0g(6.0mmol)化合物Int-7分散在80ml的甲苯中，加入3.5g(13.5mmol)的N-苯基二苯并[b,d]呋喃-4-胺(CAS:743453-07-8)，再加入1.7g(17.7mmol)的叔丁醇钠、55.5mg(0.06mmol)的Pd2(dba)3催化剂和0.25ml的10％叔丁基磷甲苯溶液，升温至110℃搅拌反应12小时，反应结束后，加入50ml的水，分出有机相，水相用甲苯萃取，收集有机相，干燥，过滤，滤液减压浓缩干，用硅胶柱分离纯化，得到5.6g的SLC-B01，浅黄色固体，收率54％。1H-NMR(δ，CDCl3)：8.050(2H,d)，7.984(2H,s)，7.791(2H,s)，7.573～7.533(2H,m)，7.503～7.425(4H,m)，7.328～7.221(4H,m)，7.242～7.083(10H,m)，6.902～6.834(2H,m)，3.424(4H,t)，2.060(4H,t)，0.995(12H,s)。
实施例2
化合物SLC-B02的制备：
Figure GDA0003307705160000261
参照实施例1第八步的制备方法，将实施例1第八步中的N-苯基二苯并[b,d]呋喃-4-胺替换为N-(4-异丙基苯基)二苯并[b,d]呋喃-4-胺(CAS:1252914-26-3)，得到黄色固体，收率60％。1H-NMR(δ，CDCl3)：8.053(2H,d)，7.988(2H,s)，7.794(2H,s)，7.558～7.530(2H,m)，7.501～7.476(4H,m)，7.322～7.253(4H,m)，7.246～7.085(8H,m)，6.901～6.839(2H,m)，3.423(4H,t)，2.947(2H,t)，2.062(4H,t)，1.213(6H,s)1.196(6H,s)，0.993(12H,s)。
实施例3
化合物SLC-B10的制备：
Figure GDA0003307705160000262
参照实施例1第八步的制备方法，将实施例1第八步中的N-苯基二苯并[b,d]呋喃-4-胺替换为双联苯基胺(CAS:102113-98-4)，得到黄色固体，收率65％。1H-NMR(δ，CDCl3)：7.983(2H,s)，7.795(2H,s)，7.561～7.415(16H,m)，7.358～7.279(8H,t)，7.240～7.163(8H,m)，7.145～7.066(4H,m)，3.054(4H,m)，1.396(4H,m)，0.996(12H,s)。
实施例4
化合物SLC-B27的制备：
Figure GDA0003307705160000271
参照实施例1第八步的制备方法，将实施例1第八步中的N-苯基二苯并[b,d]呋喃-4-胺替换为N-(4-异丙基苯基)二苯并[b,d]噻吩-4-胺(CAS:1643535-60-7)，得到黄色固体，收率58％。1H-NMR(δ，CDCl3)：8.254(2H,d)，8.096(2H,d)，7.596(4H,s)，7.547～7.529(2H,m)，7.474～7.295(8H,m)，7.272～7.067(6H,m)，6.933～6.912(2H,d)，3.382(4H,t)，2.674～2.655(2H,m)，1.592(4H,t)，1.205(6H,s)，1.198(6H,s)，0.995(12H,s)。
实施例5
化合物SLC-B82的制备：
Figure GDA0003307705160000272
参照实施例1第八步的制备方法，将实施例1第八步中的N-苯基二苯并[b,d]呋喃-4-胺替换为N-联苯基二苯并[b,d]呋喃-4-胺(CAS:1318338-47-4)，得到黄色固体，收率52％。1H-NMR(δ，CDCl3)：7.983～7.965(2H,m)，7.839～7.795(4H,m)，7.599～7.535(6H,m)，7.321～7.217(10H,t)，7.192～7.069(12H,m)，6.879～6.858(2H,m)，2.907～2.864(4H,m)，1.639～1.596(4H,m)，0.994(12H,s)。
实施例6
化合物SLC-B93的制备：
Figure GDA0003307705160000281
参照实施例1第八步的制备方法，将实施例1第八步中的N-苯基二苯并[b,d]呋喃-4-胺替换为N-(4-三甲硅基苯基)二苯并[b,d]呋喃-4-胺(CAS:1252914-28-5)，得到黄色固体，收率62％。1H-NMR(δ，CDCl3)：7.986(2H,s)，7.558～7.533(2H,m)，7.519～7.477(2H,m)，7.287～7.255(2H,m)，7.246～7.087(4H,m)，6.903～6.840(2H,m)，3.041～3.018(4H,m)，1.899～1.876(4H,m)，1.215(6H,s)1.195(6H,s)，0.992(12H,s)，0.018(18H,s)。
实施例7
化合物SLC-B97的制备：
Figure GDA0003307705160000282
参照实施例1第八步的制备方法，将实施例1第八步中的N-苯基二苯并[b,d]呋喃-4-胺替换为N-(4-甲基苯基)二苯并[b,d]噻吩-4-胺(CAS:1970231-05-0)，得到黄色固体，收率52％。1H-NMR(δ，CDCl3)：8.253(2H,d)，8.098(2H,d)，7.595(4H,s)，7.548～7.527(2H,m)，7.355～7.302(2H,m)，7.183～7.117(6H,m)，6.995～6.920(8H,dd)，2.907～2.864(4H,m)，2.114(6H,s)，1.639～1.596(4H,m)，0.995(12H,s)。
实施例8
化合物SLC-B134的制备：
Figure GDA0003307705160000291
参照实施例1第八步的制备方法，将实施例1第八步中的N-苯基二苯并[b,d]呋喃-4-胺替换为N-(4-联苯基)-9,9-二甲基芴-1-胺(CAS:1421789-17-4)，得到黄色固体，收率47％。1H-NMR(δ，CDCl3)：7.753(2H,d)，7.572(2H,d)，7.405(4H,s)，7.393～7.372(6H,m)，7.348～7.196(12H,m)，7.184～7.099(8H,m)，7.024～7.003(2H,d)，2.905～2.866(4H,m)，1.343～1.298(4H,m)，1.027(12H,s)，0.996(12H,s)。
实施例9
化合物SLC-B150的制备：
Figure GDA0003307705160000292
参照实施例1第八步的制备方法，将实施例1第八步中的N-苯基二苯并[b,d]呋喃-4-胺替换为N-(4-(叔丁基)苯基)菲-2-胺(CAS:1430393-31-9)，得到黄色固体，收率64％。1H-NMR(δ，CDCl3)：8.258(2H,s)，8.147～8.128(2H,d)，7.954～7.936(2H,d)，7.674～7.646(6H,m)，7.424～7.302(6H,m)，7.183～7.099(4H,m)，7.024～7.003(4H,d)，6.765～6.746(4H,d)，3.394～3.223(4H,m)，1.638～1.595(4H,m)，1.223(18H,s)，0.994(12H,s)。
实施例10
化合物SLC-B191的制备：
Figure GDA0003307705160000301
参照实施例1第八步的制备方法，将实施例1第八步中的N-苯基二苯并[b,d]呋喃-4-胺替换为N-(对甲苯基)菲-9-胺(CAS:79918-21-1)，得到黄色固体，收率60％。1H-NMR(δ，CDCl3)：8.257(2H,s)，8.148～8.129(2H,m)，7.964～7.898(4H,d)，7.426～7.285(8H,m)，7.211(2H，s)，7.183～7.099(4H,m)，7.026～7.005(4H,d)，6.766～6.747(4H,d)，3.396～3.225(4H,m)，2.347(6H,s)，1.636～1.592(4H,m)，0.995(12H,s)。
实施例11
图1所示的OLED元件的制备
图1所示的OLED元件包括基板1、设于基板1上的阳极层2、设于阳极层2上的空穴注入层3、设于空穴注入层3上的空穴传输层4、设于空穴传输层4上的电子阻挡层5、设于电子阻挡层5上的有机发光层6、设于有机发光层6上的空穴阻挡层7、设于空穴阻挡层7上的电子传输层8、设于电子传输层8上的阴极层9。
上述OLED元件的制备方法包括如下步骤：
1)将涂布了ITO导电层的玻璃基片在清洗剂中超声处理30分钟，在去离子水中冲洗，在丙酮/乙醇混合溶剂中超声30分钟，在洁净的环境下烘烤至完全干燥，用紫外光清洗机照射10分钟，并用低能阳离子束轰击表面。
2)把上述处理好的ITO玻璃基片置于真空腔内，抽真空至1×10-5～9×10-3Pa，在上述阳极层膜上继续分别蒸镀化合物DNTPD作为空穴注入层，蒸镀速率为0.1nm/s，蒸镀膜厚为40nm；在上述空穴注入层膜上继续蒸镀NPB为空穴传输层，蒸镀速率为0.1nm/s，蒸镀膜厚为10nm；
3)在空穴传输层上继续蒸镀一层化合物QIFA作为电子阻挡层，其蒸镀速率为0.1nm/s，蒸镀膜厚为1nm；
4)在电子阻挡层上继续蒸镀一层本发明的式I所示化合物和α,β-ADN作为有机发光层，其中，α,β-ADN为主体材料和本发明的式I所示化合物为掺杂材料，式I所示化合物与α,β-ADN的蒸镀速率比为1：100，式I所示化合物在α,β-ADN中的掺杂浓度为4％，其蒸镀总速率为0.1nm/s，蒸镀膜厚为20nm；
5)在上述有机发光层上再继续蒸镀一层化合物TPBI作为空穴阻挡层，其蒸镀速率为0.1nm/s，蒸镀膜厚为10nm；
6)在上述空穴阻挡层上再继续蒸镀一层化合物Liq作为元件的电子传输层，蒸镀速率为0.1nm/s，蒸镀膜厚为20nm；最后，在上述电子传输层之上依次蒸镀镁/银合金层作为元件的阴极层，其中镁/银合金层的蒸镀速率为2.0～3.0nm/s，蒸镀膜厚为100nm；
按照与上相同的步骤，仅将步骤4)所用的式I所示化合物替换为化合物SLC-B02，得到本发明提供的OLED-1；
按照与上相同的步骤，仅将步骤4)所用式I所示化合物替换为化合物SLC-B10，得到本发明提供的OLED-2；
按照与上相同的步骤，仅将步骤4)所用式I所示化合物替换为化合物SLC-B93，得到本发明提供的OLED-3；
按照与上相同的步骤，仅将步骤4)所用式I所示化合物替换为化合物SLC-B134，得到本发明提供的OLED-4；
按照与上相同的步骤，仅将步骤4)所用式I所示化合物替换为化合物SLC-B191，得到本发明提供的OLED-5；
按照与上相同的步骤，仅将步骤4)所用式I所示化合物替换为化合物BD01，得到对比元件OLED-6；
所得元件OLED-1至OLED-6的性能检测结果如表2所示：
表2性能检测结果
Figure GDA0003307705160000311
上述实施例11和实施例12中使用的化合物结构如下：
Figure GDA0003307705160000321
结论：从性能测试结果分析，本发明的有机化合物，色度坐标在深蓝区域，元件的外量子效率和寿命均超过了目前己知的蓝光材料，而且元件的启亮电压均在4.0V以下，相较于对比元件的5.4V电压降低了很多。由此能够以低耗电实现颜色再现性高的蓝光装置。
产业上的应用可能性
本发明的有机电致发光元件可以在壁挂电视、平板显示器、照明等的平面发光体、复印机、打印机、液晶显示器的背光源或计量仪器类等电子设备的光源，显示板、标识灯等中应用。
显然，本发明的上述实施例仅仅是为清楚地说明本发明所作的举例，而并非是对本发明的实施方式的限定，对于所属领域的普通技术人员来说，在上述说明的基础上还可以做出其它不同形式的变化或变动，这里无法对所有的实施方式予以穷举，凡是属于本发明的技术方案所引伸出的显而易见的变化或变动仍处于本发明的保护范围之列。

Claims (8)

1.一种有机化合物，其特征在于，为式I所示的化合物，所述式I所示的化合物选自以下的化合物：
Figure FDA0003240694110000011
Figure FDA0003240694110000021
Figure FDA0003240694110000031
Figure FDA0003240694110000041
Figure FDA0003240694110000051
Figure FDA0003240694110000061
Figure FDA0003240694110000071
Figure FDA0003240694110000081
Figure FDA0003240694110000091
Figure FDA0003240694110000101
Figure FDA0003240694110000111
Figure FDA0003240694110000121
Figure FDA0003240694110000131
Figure FDA0003240694110000141
Figure FDA0003240694110000151
2.一种有机电致发光材料，其特征在于，包含一种以上的权利要求1所述的有机化合物。
3.一种有机电致发光元件，其特征在于，所述有机电致发光元件包括第一电极、第二电极和置于所述第一电极、所述第二电极之间的一个或多个包含权利要求1所述的有机化合物的有机发光层。
4.如权利要求3所述的有机电致发光元件，其特征在于，所述第一电极、第二电极之间还具有一层或多层的选自电子注入层、电子输送层、空穴阻挡层、电子阻挡层、空穴输送层、空穴注入层的层。
5.如权利要求3或4所述的有机电致发光元件，其特征在于，所述有机发光层包含作为主发光体的选自萘、蒽、芘、苝、菲、荧蒽、
Figure FDA0003240694110000152
苯并蒽、并五苯以及它们的衍生物中的一种以上，以及作为掺杂物的一种以上的权利要求1所述的有机化合物。
6.一种电子设备，其含有权利要求3～5的任一项所述的有机电致发光元件。
7.一种如权利要求1所述的有机化合物在制备有机电致发光元件中的应用。
8.一种如权利要求1所述的有机化合物在制备有机电致发光材料中的应用。
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