CN113816909A - 一种含菲结构的有机电致发光材料及其器件 - Google Patents

一种含菲结构的有机电致发光材料及其器件 Download PDF

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CN113816909A
CN113816909A CN202111080676.2A CN202111080676A CN113816909A CN 113816909 A CN113816909 A CN 113816909A CN 202111080676 A CN202111080676 A CN 202111080676A CN 113816909 A CN113816909 A CN 113816909A
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nitro
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fluoro
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CN113816909B (zh
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穆广园
庄少卿
陶康
王林
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Wuhan Sunshine Optoelectronics Tech Co ltd
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Abstract

本发明涉及光电材料应用科技领域，公开了一种含菲结构的有机电致发光材料及其器件。该有机电致发光材料通过对含菲核心结构特定位点引入烷基及特定官能团对核心结构进行的精细调控，提供了一种综合性能优良的发光主体材料，有效改善了目前发光主体材料分子内电荷转移及发光红移等问题，使用该材料制作的有机电致发光器件在驱动电压、电流效率、寿命等方面具有显著进步。

Description

一种含菲结构的有机电致发光材料及其器件
技术领域
本发明属于光电材料应用科技领域，具体涉及一种含菲结构的有机电致发光材料及其器件。
背景技术
在电场作用下，有机电致发光材料(OLED)具有将电能转化为光能的特性，与其他发光技术相比，OLED发光具有一系列的优点，如自主发光、高效、节能、轻薄等，在平板显示、固态照明等方面表现出美好的应用前景。
高能量的蓝光材料可通过能量转移到低能量的绿光和红光等有机发光材料，这对于制备全发光的有机电致发光器件具有重要意义。然而，目前应用最多的有机小分子蓝光荧光材料由于自身的宽带隙，在器件中电荷注入困难，此外，材料设计过程中的π-π共轭也容易导致较强的分子内电荷转移，从而导致材料发光红移，很难兼顾效率和发光颜色，因此，综合性能优越的蓝光材料仍然较为缺乏。
含菲结构单元具有较高的三线态能级和较宽的能隙，是一种性能优异的蓝光结构，通过对含菲核心结构特定位点进行烷基的引入则可以有效减少分子间的π-π堆积，化合物可以同时兼具较高的荧光量子效率及较弱的分子内电荷转移，此外，通过引入适当的空穴或电子传输型的侧基，化合物电荷传输更加平衡。
发明内容
本发明的目的在于提供一种含菲结构的有机电致发光材料及其器件，解决目前蓝光发光材料发光效率、发光颜色、寿命等方面的缺陷，从而使得OLED器件在驱动电压、电流效率、寿命等方面具有优良的综合性能。
本发明第一个方面提供了一种含菲结构的有机电致发光材料，其化合物结构通式如式1所示：
Figure BDA0003263882640000011
所述式1中，
L0选自单键，未取代的或由C1～20的烷烃基、C1～20的烷氧基、腈基、硝基、氟基取代的亚苯基，未取代的或由C1～20的烷烃基、C1～20的烷氧基、腈基、硝基、氟基取代的亚联苯基，未取代的或由C1～20的烷烃基、烷氧基、腈基、硝基、氟基取代的亚萘基；
R0选自氢、氟基、硝基、氰基、C1～20的烷基、C1～20的烷氧基、C1～20的烷硫基、C1～20的硅烷基、C6～50的芳基、C3～50的杂芳基、C6～50的芳胺基、C6～50的芳氧基、C6～50的芳硫基；
CY为下述化学式2所表示的基团，
Figure BDA0003263882640000021
其中，*是与上述式1结合的部位；
R1为C1～20的烷基；
X为N，Y选自N(R2)、O或S；
R2选自C1～20的烷基、C6～50的芳基、C3～50的杂芳基。
进一步的，式1进一步由化学式(1-1)至(1-6)中任一表示：
Figure BDA0003263882640000022
所述化学式(1-1)至(1-6)中，
L0和R0的定义与所述式1相同，R1和R2的定义与所述化学式2相同。
进一步的，所述R1选自甲基、乙基。
进一步的，所述L0选自单键、未取代的亚苯基、未取代的亚萘基。
进一步的，所述R2选自：未取代的或由氟基、硝基、氰基、C1-C6的烷基、C1-C6的烷氧基、萘基取代的苯基，未取代的或由氟基、硝基、氰基、C1-C6的烷基、C1-C6的烷氧基、苯基取代的联苯基，未取代的或由氟基、硝基、氰基、C1-C6的烷基、C1-C6的烷氧基、苯基取代的萘基。
进一步的，所述R0选自：
Figure BDA0003263882640000023
其中，R3-R8、R12-R14分别独立的选自：氢，氟基，硝基，氰基，C1-C6的烷烃基，未取代的或由氟基、硝基、氰基、C1-C6的烷烃基取代的苯基，未取代的或由氟基、硝基、氰基、C1-C6的烷烃基取代的联苯基；
R9-R11、R15-R18分别独立的选自：
C1-C6的烷烃基，未取代的或由C1-C6的烷烃基、C1-C6的烷氧基、腈基、硝基、氟基取代的苯基，未取代的或由C1-C6的烷烃基、C1-C6的烷氧基、腈基、硝基、氟基取代的联苯基，未取代的或由C1-C6的烷烃基、C1-C6的烷氧基、腈基、硝基、氟基取代的三联苯基，未取代的或由C1-C6的烷烃基、C1-C6的烷氧基、腈基、硝基、氟基、苯基取代的萘基；
Ar1、Ar2、Ar3分别独立的表示为不存在或为单环芳烃，当Ar1、Ar2、Ar3为单环芳烃时，所述Ar1、Ar2、Ar3与连接的萘环之间直接稠合；
Y1选自：O、S、N(R19)、C(R20)(R21)；
Y2、Y3分别独立的选自：O、S、N(R22)；
R19、R22分别独立的选自：甲基，乙基，未取代的或由甲基、甲氧基、腈基、硝基、氟基取代的苯基，未取代的或由甲基、甲氧基、腈基、硝基、氟基取代的联苯基，未取代的或由甲基、甲氧基、腈基、硝基、氟基取代的萘基；
R20与R21相同，独立的选自甲基，乙基，或者苯基，当R20、R21选自苯基时，基团之间相互独立或通过单键连接；
Z为CH、N或C(R23)，且
Figure BDA0003263882640000031
中Z为N的个数为不相邻的1-3个，R23独立的选自苯基、甲苯基、腈基苯基、联苯基、萘基、二苯并呋喃基、二苯并噻吩基、9,9-二甲基芴基、咔唑基苯基、苯基咔唑基；
Q为CH或N，各基团中，Q为N的个数为1个或不相邻的2个。
进一步的，
Figure BDA0003263882640000032
可进一步的表示为：
Figure BDA0003263882640000033
Figure BDA0003263882640000034
可进一步的表示为：
Figure BDA0003263882640000035
Figure BDA0003263882640000036
可进一步的表示为：
Figure BDA0003263882640000037
Figure BDA0003263882640000038
Figure BDA0003263882640000041
可进一步的表示为：
Figure BDA0003263882640000042
Figure BDA0003263882640000043
可进一步的表示为：
Figure BDA0003263882640000044
Figure BDA0003263882640000045
Figure BDA0003263882640000046
可进一步的表示为：
Figure BDA0003263882640000047
Figure BDA0003263882640000048
Figure BDA0003263882640000049
其中，Z各自独立的选自CH、N，且各基团中至少有一个Z选自N；
Figure BDA00032638826400000410
可进一步表示为：
Figure BDA00032638826400000411
Figure BDA00032638826400000412
Figure BDA0003263882640000051
Figure BDA0003263882640000052
可进一步表示为：
Figure BDA0003263882640000053
Figure BDA0003263882640000054
其中，Q为N的个数为1，其余Q为CH；
Figure BDA0003263882640000055
可进一步表示为：
Figure BDA0003263882640000056
Figure BDA0003263882640000057
可进一步表示为：
Figure BDA0003263882640000058
Figure BDA0003263882640000059
Figure BDA00032638826400000510
可进一步表示为：
Figure BDA00032638826400000511
Figure BDA00032638826400000512
可进一步表示为：
Figure BDA00032638826400000513
Figure BDA00032638826400000514
可进一步表示为：
Figure BDA00032638826400000515
Figure BDA00032638826400000516
可进一步表示为：
Figure BDA00032638826400000517
Figure BDA00032638826400000518
可进一步表示为：
Figure BDA00032638826400000519
Figure BDA0003263882640000061
可进一步表示为：
Figure BDA0003263882640000062
Figure BDA0003263882640000063
可进一步表示为：
Figure BDA0003263882640000064
进一步的，所述式1选自下述化合物：
Figure BDA0003263882640000071
Figure BDA0003263882640000081
Figure BDA0003263882640000091
Figure BDA0003263882640000101
本发明第二个方面提供了一种有机电致发光器件，主要包括阴极、阳极和两电极之间的有机层，或者主要包括出光层、阴极、阳极和两电极之间的有机层，所述两电极之间的有机层包上述任一所述的含菲结构的有机电致发光材料。
进一步的，所述两电极之间的有机层包括发光层，所述发光层由发光主体和发光客体组成，所述发光主体或发光客体包含上述任一所述的含菲结构的有机电致发光材料。
本发明提供的有机电致发光材料化合物分子中包含的菲并五元杂环的稠合核心结构处于同一共轭平面，这赋予了化合物分子较高的三线态能级和较宽的能隙，因此化合物分子可以获得较高的蓝光荧光量子效率；核心结构中甲基或乙基的引入相比于现有技术中的芳香性基团，对活性位点进行封装的同时，使得化合物核心具有更短的共轭结构，有利于深蓝光发射，另一方面可以有效减弱分子间的相互作用，减少聚集态中分子间的紧密堆集，更有利于化合物材料的无针孔高质量蒸镀成膜；此外，通过对核心结构引入不同种类的给电子型或吸电子型侧基进行修饰，可以进一步增强分子扭曲，也可以有效改善化合物分子内电荷传输平衡性，从而使得本发明实现高效的深蓝光发射，在器件的驱动电压、电流效率、寿命等综合性能上取得显著进步。
具体实施方式
应当理解的是，此处所描述的具体实施方式仅用于说明和解释本发明，并不用于限制本发明。
中间体int-1的合成
Figure BDA0003263882640000121
S1.在250mL反应瓶中，加入(2-甲基苯并噁唑-4-基)硼酸(14.16g,80mmol)、2-溴-4-氯苯甲醛(19.31g,88mmol)、碳酸钾(22.08g,160mmol)、150mL体积比为2:1:1的甲苯/乙醇/水混合溶剂，通入氮气排空气，然后，加入四(三苯基膦)钯(0.46g,0.4mmol)，加热至85℃，搅拌反应8h左右，然后冷却至室温，过滤，滤液分液，有机相浓缩，与滤饼一起用乙醇和/或四氢呋喃进行纯化，即可得到16.30g中间体a1，收率75％。
S2.在500mL反应瓶中，加入甲氧基甲基三苯基氯化膦(20.57g,60mmol)、叔丁醇钾(6.73g,60mmol)，200mL四氢呋喃，降温至0℃下搅拌反应0.5小时，然后加入中间体a1(10.87g,40mmol)，室温下搅拌反应2小时，加水猝灭反应，用乙酸乙酯萃取，水洗，无水硫酸钠干燥，过滤，浓缩后通过柱色谱即可得到10.55g中间体b1，产率88％。
S3.在100mL反应瓶中，加入中间体b1(6.00g,20mmol)、氯化镍(0.13g,1mmol)、60mL1，2-二氯乙烷，室温下搅拌反应2小时，过滤，滤液浓缩，然后通过柱色谱分离即可得到4.44g中间体int-1，收率83％。
质谱仪MALDI-TOF-MS(m/z)＝267.7086，理论分子量：267.7120，元素分析：理论值：C16H10N(％)：C71.78；H3.77；N5.23；实测值：C71.76；H3.78；N5.22。
中间体int-2的合成
Figure BDA0003263882640000122
S1.将中间体int-1中步骤S1的(2-甲基苯并噁唑-4-基)硼酸替换为(2-甲基-1-苯基-1氢-苯并咪唑-7-基)硼酸(20.17g,80mmol)、2-溴-4-氯苯甲醛替换成2-溴-5-氯苯甲醛(19.31g,88mmol)，其他合成过程按照中间体int-1的步骤S1，即可得到19.42g中间体a2，收率70％；
S2.将中间体int-1中步骤S2的中间体a1替换为中间体a2(13.87g,40mmol)、其他合成过程按照中间体int-1的步骤S2，即可得到12.60g中间体b2，收率84％；
S3.将中间体int-1中步骤S3的中间体b1替换为中间体b2(7.50g,20mmol)、其他合成过程按照中间体int-1的步骤S3，即可得到5.48g中间体int-2，收率80％。
质谱仪MALDI-TOF-MS(m/z)＝342.8305，理论分子量：342.8260，元素分析：理论值：C22H15N2(％)：C77.08；H4.41；N8.17；实测值：C77.09；H4.40；N8.19。
中间体int-3的合成
Figure BDA0003263882640000123
S1.将中间体int-1中步骤S1的(2-甲基苯并噁唑-4-基)硼酸替换为(2-乙基苯并噻唑-4-基)硼酸(16.56g,80mmol)，其他合成过程按照中间体int-1的步骤S1，即可得到17.62g中间体a2，收率73％；
S2.将中间体int-1中步骤S2的中间体a1替换为中间体a3(12.07g,40mmol)、其他合成过程按照中间体int-1的步骤S2，即可得到11.34g中间体b2，收率86％；
S3.将中间体int-1中步骤S3的中间体b1替换为中间体b3(6.60g,20mmol)、其他合成过程按照中间体int-1的步骤S3，即可得到4.80g中间体int-2，收率82％。
质谱仪MALDI-TOF-MS(m/z)＝297.8062，理论分子量：297.8000，元素分析：理论值：C17H12N(％)：C68.57；H4.06；N4.70；实测值：C68.56；H4.08；N4.68。
按照中间体int-1、中间体int-2及中间体int-3的合成方法，以基本相同的合成方法(相同的反应摩尔比与反应条件)，即可制备得到：
Figure BDA0003263882640000131
Figure BDA0003263882640000132
合成实施例1：合成化合物(A-2)
Figure BDA0003263882640000133
S1.在50mL反应瓶中，加入9-氯-2-甲基菲并[4,3-d]噁唑(2.68g,10mmol)、(4-苯基萘-1-基)硼酸(2.48g,10mmol)、碳酸钾(2.76g,20mmol)、25mL体积比为2:1:1的甲苯/乙醇/水混合溶剂，通入氮气排空气，然后，加入四(三苯基膦)钯(0.06g,0.05mmol)，加热至85℃，搅拌反应8h左右，然后冷却至室温，过滤，滤液分液，有机相浓缩，与滤饼一起用10:1的石油醚与二氯甲烷在硅胶柱中淋洗，浓缩，即可得到3.40g化合物(A-2)，收率78％。
质谱仪MALDI-TOF-MS(m/z)＝435.5197，理论分子量：435.5260，元素分析：理论值：C32H21N(％)：C88.25；H4.86；N3.22；实测值：C88.27；H4.85；N3.23。
合成实施例2：合成化合物(A-8)
Figure BDA0003263882640000134
S1.将合成实施例1步骤S1的9-氯-2-甲基菲并[4,3-d]噁唑替换为10-氯-2-甲基菲并[4,3-d]噁唑(2.68g,10mmol)、(4-苯基萘-1-基)硼酸替换成(4-(4,6-二苯基-1,3,5-三嗪-2-基)苯基)硼酸(3.53g,10mmol)，其他合成过程按照合成实施例1步骤S1，即可得到3.89g化合物(A-8)，收率72％。
质谱仪MALDI-TOF-MS(m/z)＝540.6319，理论分子量：540.6260，元素分析：理论值：C37H24N4(％)：C82.20；H4.47；N10.36；实测值：C82.18；H4.47；N10.38。
合成实施例3：合成化合物(A-18)
Figure BDA0003263882640000141
S1.将合成实施例1步骤S1的9-氯-2-甲基菲并[4,3-d]噁唑替换为10-氯-2-甲基菲并[4,3-d]噻唑(2.84g,10mmol)、(4-苯基萘-1-基)硼酸替换成(4-(苯并[d]噻唑-2-基)苯基)硼酸(2.55g,10mmol)，其他合成过程按照合成实施例1步骤S1，即可得到3.39g化合物(A-18)，收率74％。
质谱仪MALDI-TOF-MS(m/z)＝458.5905，理论分子量：458.5970，元素分析：理论值：C29H18N2(％)：C75.95；H3.96；N6.11；实测值：C75.95；H3.97；N6.09。
合成实施例4：合成化合物(A-20)
Figure BDA0003263882640000142
S1.将合成实施例1步骤S1的9-氯-2-甲基菲并[4,3-d]噁唑替换为9-氯-2-甲基菲并[4,3-d]噻唑(2.84g,10mmol)、(4-苯基萘-1-基)硼酸替换成(4-(苯并[d]噻唑-2-基)苯基)硼酸(2.55g,10mmol)，其他合成过程按照合成实施例1步骤S1，即可得到3.49g化合物(A-18)，收率76％。
质谱仪MALDI-TOF-MS(m/z)＝458.6024，理论分子量：458.5970，元素分析：理论值：C29H18N2(％)：C75.95；H3.96；N6.11；实测值：C75.96；H3.94；N6.12。
合成实施例5：合成化合物(A-31)
Figure BDA0003263882640000143
S1.在50mL反应瓶中，加入9-氯-2-甲基-3-苯基-3氢-菲并[3,4-d]咪唑(3.43g,10mmol)、3-苯基-9氢-咔唑(2.03g,12mmol)、碳酸钾(2.76g,20mmol)和30mL N,N-二甲基乙酰胺。通入氮气，加入碘化亚铜0.19g(1mmol)和邻菲啰啉0.36g(2mmol)，加热回流搅拌8h，将温度冷却至室温，加水，分液，有机相减压蒸馏，乙醇纯化，即可得到3.90g化合物(A-31)，收率82％。
质谱仪MALDI-TOF-MS(m/z)＝475.5507，理论分子量：475.5550，元素分析：理论值：C32H21N5(％)：C80.82；H4.45；N14.73；实测值：C80.84；H4.44；N14.73。
合成实施例6：合成化合物(A-42)
Figure BDA0003263882640000151
S1.将合成实施例1步骤S1的9-氯-2-甲基菲并[4,3-d]噁唑替换为10-氯-2-甲基菲并[3,4-d]噁唑(2.68g,10mmol)、(4-苯基萘-1-基)硼酸替换成(4-(4,6-二苯基-1,3,5-三嗪-2-基)苯基)硼酸(3.53g,10mmol)，其他合成过程按照合成实施例1步骤S1，即可得到4.05g化合物(A-42)，收率75％。
质谱仪MALDI-TOF-MS(m/z)＝540.6183，理论分子量：540.6260，元素分析：理论值：C37H24N4(％)：C82.20；H4.47；N10.36；实测值：C82.21；H4.46；N10.37。
合成实施例7：合成化合物(A-44)
Figure BDA0003263882640000152
S1.将合成实施例1步骤S1的9-氯-2-甲基菲并[4,3-d]噁唑替换为10-氯-2-甲基菲并[3,4-d]噁唑(2.68g,10mmol)、(4-苯基萘-1-基)硼酸替换成二苯并[b,d]噻吩-2-基硼酸(2.28g,10mmol)，其他合成过程按照合成实施例1步骤S1，即可得到3.20g化合物(A-44)，收率77％。
质谱仪MALDI-TOF-MS(m/z)＝415.5142，理论分子量：415.5100，元素分析：理论值：C28H17N(％)：C80.94；H4.12；N3.37；实测值：C80.94；H4.14；N3.35。
合成实施例8：合成化合物(A-49)
Figure BDA0003263882640000153
S1.将合成实施例1步骤S1的9-氯-2-甲基菲并[4,3-d]噁唑替换为9-氯-2-甲基菲并[3,4-d]噻唑(2.84g,10mmol)、(4-苯基萘-1-基)硼酸替换成[1,1'-二苯基]-4-基硼酸(1.98g,10mmol)，其他合成过程按照合成实施例1步骤S1，即可得到3.21g化合物(A-49)，收率80％。
质谱仪MALDI-TOF-MS(m/z)＝401.5203，理论分子量：401.5270，元素分析：理论值：C28H19N(％)：C83.76；H 4.77；N3.49；实测值：C83.74；H 4.78；N3.50。
合成实施例9：合成化合物(A-70)
Figure BDA0003263882640000154
S1.将合成实施例1步骤S1的9-氯-2-甲基菲并[4,3-d]噁唑替换为9-氯-2-甲基-1-苯基-1氢-菲并[3,4-d]咪唑(3.43g,10mmol)、(4-苯基萘-1-基)硼酸替换成(3-(1-苯基-1氢-苯并咪唑-2-基)苯基)硼酸(3.14g,10mmol)，其他合成过程按照合成实施例1步骤S1，即可得到4.21g化合物(A-49)，收率73％。
质谱仪MALDI-TOF-MS(m/z)＝576.7012，理论分子量：576.7030，元素分析：理论值：C41H28N4(％)：C85.39；H4.89；N9.72；实测值：C85.41；H4.87；N9.71。
合成实施例10：合成化合物(B-4)
Figure BDA0003263882640000161
S1.将合成实施例1步骤S1的9-氯-2-甲基菲并[4,3-d]噁唑替换为10-氯-2-乙基菲并[4,3-d]噁唑(2.82g,10mmol)、(4-苯基萘-1-基)硼酸替换成(4-(4,6-二苯基-1,3,5-三嗪-2-基)苯基)硼酸(3.53g,10mmol)，其他合成过程按照合成实施例1步骤S1，即可得到3.94g化合物(B-4)，收率71％。
质谱仪MALDI-TOF-MS(m/z)＝554.6591，理论分子量：554.6530，元素分析：理论值：C38H26N4(％)：C82.29；H4.73；N10.10；实测值：C82.30；H4.74；N10.08。
合成实施例11：合成化合物(B-8)
Figure BDA0003263882640000162
S1.将合成实施例1步骤S1的9-氯-2-甲基菲并[4,3-d]噁唑替换为9-氯-2-乙基菲并[4,3-d]噁唑(2.82g,10mmol)、(4-苯基萘-1-基)硼酸替换成(4-(苯并噁唑-2-基)苯基)硼酸(2.39g,10mmol)，其他合成过程按照合成实施例1步骤S1，即可得到3.48g化合物(B-8)，收率79％。
质谱仪MALDI-TOF-MS(m/z)＝440.5078，理论分子量：440.5020，元素分析：理论值：C30H20N2(％)：C81.80；H4.58；N6.36；实测值：C81.78；H4.57；N6.38。
合成实施例12：合成化合物(B-12)
Figure BDA0003263882640000163
S1.将合成实施例1步骤S1的9-氯-2-甲基菲并[4,3-d]噁唑替换为10-氯-2-乙基菲并[4,3-d]噻唑(2.98g,10mmol)、(4-苯基萘-1-基)硼酸替换成(4-(9,9-二甲基-9氢-芴-2-基)苯基)硼酸(3.14g,10mmol)，其他合成过程按照合成实施例1步骤S1，即可得到3.93g化合物(B-12)，收率74％。
质谱仪MALDI-TOF-MS(m/z)＝531.7106，理论分子量：531.7170，元素分析：理论值：C38H29N(％)：C85.84；H5.50；N2.63；实测值：C85.84；H5.52；N2.61。
合成实施例13：合成化合物(B-21)
Figure BDA0003263882640000164
S1.将合成实施例1步骤S1的9-氯-2-甲基菲并[4,3-d]噁唑替换为10-氯-2-乙基菲并[4,3-d]噻唑(2.98g,10mmol)、(4-苯基萘-1-基)硼酸替换成(4-([1,2,4]三唑并[1,5-a]吡啶-2-基)苯基)硼酸(2.39g,10mmol)，其他合成过程按照合成实施例1步骤S1，即可得到3.52g化合物(B-21)，收率77％。
质谱仪MALDI-TOF-MS(m/z)＝456.5704，理论分子量：456.5670，元素分析：理论值：C29H20N4(％)：C76.29；H4.42；N12.27；实测值：C76.31；H4.40；N12.28。
合成实施例14：合成化合物(B-28)
Figure BDA0003263882640000171
S1.将合成实施例5步骤S1的9-氯-2-甲基-3-苯基-3氢-菲并[3,4-d]咪唑替换为9-氯-2-乙基-3-苯基-3氢-菲并[3,4-d]咪唑(3.57g,10mmol)、3-苯基-9氢-咔唑替换成9氢-咔唑(1.67g,10mmol)，其他合成过程按照合成实施例5步骤S1，即可得到4.14g化合物(B-28)，收率85％。
质谱仪MALDI-TOF-MS(m/z)＝487.6007，理论分子量：487.6060，元素分析：理论值：C35H25N3(％)：C86.21；H5.17；N8.62；实测值：C86.20；H5.15；N8.64。
合成实施例15：合成化合物(B-41)
Figure BDA0003263882640000172
S1.将合成实施例1步骤S1的9-氯-2-甲基菲并[4,3-d]噁唑替换为9-氯-2-乙基菲并[3,4-d]噁唑(2.82g,10mmol)、(4-苯基萘-1-基)硼酸替换成(4-(二苯胺)苯基)硼酸(2.89g,10mmol)，其他合成过程按照合成实施例1步骤S1，即可得到3.53g化合物(B-41)，收率72％。
质谱仪MALDI-TOF-MS(m/z)＝490.6109，理论分子量：490.6060，元素分析：理论值：C35H26N2(％)：C85.69；H5.34；N5.71；实测值：C85.70；H5.35；N5.69。
合成实施例16：合成化合物(B-44)
Figure BDA0003263882640000173
S1.将合成实施例5步骤S1的9-氯-2-甲基-3-苯基-3氢-菲并[3,4-d]咪唑替换为9-氯-2-乙基菲并[3,4-d]噁唑(2.82g,10mmol)、3-苯基-9氢-咔唑替换成二苯基胺(1.69g,10mmol)，其他合成过程按照合成实施例5步骤S1，即可得到3.32g化合物(B-44)，收率80％。
质谱仪MALDI-TOF-MS(m/z)＝414.5017，理论分子量：414.5080，元素分析：理论值：C29H22N2(％)：C84.03；H5.35；N6.76；实测值：C84.05；H5.33；N6.77。
合成实施例17：合成化合物(B-51)
Figure BDA0003263882640000181
S1.将合成实施例1步骤S1的9-氯-2-甲基菲并[4,3-d]噁唑替换为9-氯-2-乙基菲并[3,4-d]噻唑(2.98g,10mmol)、(4-苯基萘-1-基)硼酸替换成(9-苯基-9氢-咔唑-3-基)硼酸(2.87g,10mmol)，其他合成过程按照合成实施例1步骤S1，即可得到3.58g化合物(B-51)，收率71％。
质谱仪MALDI-TOF-MS(m/z)＝504.6575，理论分子量：504.6510，元素分析：理论值：C35H24N2(％)：C83.30；H4.79；N5.55；实测值：C83.31；H4.80；N5.54。
合成实施例18：合成化合物(B-68)
Figure BDA0003263882640000182
S1.将合成实施例1步骤S1的9-氯-2-甲基菲并[4,3-d]噁唑替换为9-氯-2-乙基-1-苯基-1氢-菲并[3,4-d]咪唑(3.57g,10mmol)、(4-苯基萘-1-基)硼酸替换成(3-(4,6-二苯基嘧啶-2-基)苯基)硼酸(3.52g,10mmol)，其他合成过程按照合成实施例1步骤S1，即可得到4.21g化合物(B-68)，收率67％。
质谱仪MALDI-TOF-MS(m/z)＝628.7790，理论分子量：628.7845，元素分析：理论值：C45H32N4(％)：C85.96；H5.13；N8.91；实测值：C85.94；H5.15；N8.92。
器件实施例1
将带有120nm ITO透明薄膜的玻璃基板依次用丙酮、异丙醇和去离子水各超声清洗10min，105℃下真空干燥2h，然后进行UV臭氧洗涤15min，即将ITO玻璃基板传送至真空蒸镀机。
在形成有ITO薄膜一侧的面上，真空蒸镀三氧化钼(MoO3)，以形成10nm厚的空穴注入层；
下一步，在上述空穴注入层上，真空蒸镀4,4'-环己基二[N,N-二(4-甲基苯基)苯胺](TAPC)，以形成70nm厚的空穴传输层；
下一步，在上述空穴传输层上，真空蒸镀4,4',4”-三(咔唑-9-基)三苯胺(TCTA)，以形成10nm的电子阻挡层；
下一步，在上述电子阻挡层上，共同真空蒸镀上述合成实施例1中所制备的化合物A-2(作为发光主体材料，90wt％)与4,4'-双(9-乙基-3-咔唑乙烯基)-1,1'-联苯(BCzVBi，作为发光客体材料，10wt％)，以形成30nm厚度的发光层；
下一步，在上述发光层上，真空蒸镀3,3'-[5'-[3-(3-吡啶基)苯基][1,1':3',1”-三联苯]-3,3”-二基]二吡啶(TmPyPB)，以形成40nm厚度的电子传输层；
下一步，在上述电子传输层上，真空蒸镀氟化锂(LiF)，以形成1nm厚度的电子注入层；
最后，在上述电子注入层上，真空蒸镀铝(Al)，以形成100nm的阴极。
器件实施例2至器件实施例18
按照与器件实施例1相同的方法制备有机电致发光器件，不同的是分别使用上述合成实施例2至合成实施例18中所合成的化合物分别替换上述合成实施例1中所制备的化合物A-2。
器件对比例19至器件对比例21
除了用下述化合物C-1、C-2、C-3分别替换合成实施例1中所制备的化合物A-2外，按照与器件实施例1相同的方法制备有机电致发光器件；
Figure BDA0003263882640000191
对上述器件实施例以及器件对比例所制备的有机电致发光器件进行性能测试，结果如表1所示:
表1
Figure BDA0003263882640000192
从上表1的数据可看出，本发明提供的核心结构含菲，键接强吸电子型或强供电子型侧基的有机电致发光材料，由于菲并五元杂环的稠合核心结构上甲基或乙基的引入，对活性位点进行封装的同时，使得化合物核心具有更短的共轭结构，有利于深蓝光发射，有效减少分子间的紧密堆集，从而化合物真空蒸镀成膜良好，此外，通过本发明特定的电子传输或空穴传输基团对核心结构进行修饰，化合物分子内电荷传输平衡良好，相比于对核心结构引入苯基或联苯基等芳香性基团的化合物C-1、C-2及C-3，在器件的驱动电压、电流效率、寿命、色坐标等综合性能上具有显著的进步。
以上所述仅为本发明的较佳实施例，并不用以限制本发明，凡在本发明的精神和原则之内，所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。

Claims (10)

1.一种含菲结构的有机电致发光材料，其化合物结构通式如式1所示：
Figure FDA0003263882630000011
所述式1中，
L0选自单键，未取代的或由C1～20的烷烃基、C1～20的烷氧基、腈基、硝基、氟基取代的亚苯基，未取代的或由C1～20的烷烃基、C1～20的烷氧基、腈基、硝基、氟基取代的亚联苯基，未取代的或由C1～20的烷烃基、烷氧基、腈基、硝基、氟基取代的亚萘基；
R0选自氢、氟基、硝基、氰基、C1～20的烷基、C1～20的烷氧基、C1～20的烷硫基、C1～20的硅烷基、C6～50的芳基、C3～50的杂芳基、C6～50的芳胺基、C6～50的芳氧基、C6～50的芳硫基；
CY为下述化学式2所表示的基团，
Figure FDA0003263882630000012
其中，*是与上述式1结合的部位；
R1为C1～20的烷基；
X为N，Y选自N(R2)、O或S；
R2选自C1～20的烷基、C6～50的芳基、C3～50的杂芳基。
2.根据权利要求1所述的一种含菲结构的有机电致发光材料，其特征在于：所述式1进一步由化学式(1-1)至(1-6)中任一表示：
Figure FDA0003263882630000021
所述化学式(1-1)至(1-6)中，
L0和R0的定义与所述式1相同，R1和R2的定义与所述化学式2相同。
3.根据权利要求2所述的一种含菲结构的有机电致发光材料，其特征在于：所述R1选自甲基、乙基。
4.根据权利要求3所述的一种含菲结构的有机电致发光材料，其特征在于：所述L0选自单键、未取代的亚苯基、未取代的亚萘基。
5.根据权利要求4所述的一种含菲结构的有机电致发光材料，其特征在于：所述R2选自：未取代的或由氟基、硝基、氰基、C1-C6的烷基、C1-C6的烷氧基、萘基取代的苯基，未取代的或由氟基、硝基、氰基、C1-C6的烷基、C1-C6的烷氧基、苯基取代的联苯基，未取代的或由氟基、硝基、氰基、C1-C6的烷基、C1-C6的烷氧基、苯基取代的萘基。
6.根据权利要求5所述的一种含菲结构的有机电致发光材料，其特征在于：所述R0选自：
Figure FDA0003263882630000022
其中，R3-R8、R12-R14分别独立的选自：氢，氟基，硝基，氰基，C1-C6的烷烃基，未取代的或由氟基、硝基、氰基、C1-C6的烷烃基取代的苯基，未取代的或由氟基、硝基、氰基、C1-C6的烷烃基取代的联苯基；
R9-R11、R15-R18分别独立的选自：C1-C6的烷烃基，未取代的或由C1-C6的烷烃基、C1-C6的烷氧基、腈基、硝基、氟基取代的苯基，未取代的或由C1-C6的烷烃基、C1-C6的烷氧基、腈基、硝基、氟基取代的联苯基，未取代的或由C1-C6的烷烃基、C1-C6的烷氧基、腈基、硝基、氟基取代的三联苯基，未取代的或由C1-C6的烷烃基、C1-C6的烷氧基、腈基、硝基、氟基、苯基取代的萘基；
Ar1、Ar2、Ar3分别独立的表示为不存在或为单环芳烃，当Ar1、Ar2、Ar3为单环芳烃时，所述Ar1、Ar2、Ar3与连接的萘环之间直接稠合；
Y1选自：O、S、N(R19)、C(R20)(R21)；
Y2、Y3分别独立的选自：O、S、N(R22)；
R19、R22分别独立的选自：甲基，乙基，未取代的或由甲基、甲氧基、腈基、硝基、氟基取代的苯基，未取代的或由甲基、甲氧基、腈基、硝基、氟基取代的联苯基，未取代的或由甲基、甲氧基、腈基、硝基、氟基取代的萘基；
R20与R21相同，独立的选自甲基，乙基，或者苯基，当R20、R21选自苯基时，基团之间相互独立或通过单键连接；
Z为CH、N或C(R23)，且
Figure FDA0003263882630000031
中Z为N的个数为不相邻的1-3个，R23独立的选自苯基、甲苯基、腈基苯基、联苯基、萘基、二苯并呋喃基、二苯并噻吩基、9,9-二甲基芴基、咔唑基苯基、苯基咔唑基；
Q为CH或N，各基团中，Q为N的个数为1个或不相邻的2个。
7.根据权利要求6所述的一种含菲结构的有机电致发光材料，其特征在于：
Figure FDA0003263882630000032
可进一步的表示为：
Figure FDA0003263882630000033
Figure FDA0003263882630000034
Figure FDA0003263882630000035
可进一步的表示为：
Figure FDA0003263882630000036
Figure FDA0003263882630000041
可进一步的表示为：
Figure FDA0003263882630000042
Figure FDA0003263882630000043
Figure FDA0003263882630000044
可进一步的表示为：
Figure FDA0003263882630000045
Figure FDA0003263882630000046
Figure FDA0003263882630000047
可进一步的表示为：
Figure FDA0003263882630000048
Figure FDA0003263882630000049
Figure FDA00032638826300000410
可进一步的表示为：
Figure FDA00032638826300000411
Figure FDA00032638826300000412
Figure FDA0003263882630000051
Figure FDA0003263882630000052
其中，Z各自独立的选自CH、N，且各基团中至少有一个Z选自N；
Figure FDA0003263882630000053
可进一步表示为：
Figure FDA0003263882630000054
Figure FDA0003263882630000055
Figure FDA0003263882630000056
可进一步表示为：
Figure FDA0003263882630000057
Figure FDA0003263882630000058
其中，Q为N的个数为1，其余Q为CH；
Figure FDA0003263882630000059
可进一步表示为：
Figure FDA00032638826300000510
Figure FDA00032638826300000511
可进一步表示为：
Figure FDA00032638826300000512
Figure FDA00032638826300000513
Figure FDA0003263882630000061
可进一步表示为：
Figure FDA0003263882630000062
Figure FDA0003263882630000063
可进一步表示为：
Figure FDA0003263882630000064
Figure FDA0003263882630000065
可进一步表示为：
Figure FDA0003263882630000066
Figure FDA0003263882630000067
可进一步表示为：
Figure FDA0003263882630000068
Figure FDA0003263882630000069
可进一步表示为：
Figure FDA00032638826300000610
Figure FDA00032638826300000611
可进一步表示为：
Figure FDA00032638826300000612
Figure FDA00032638826300000613
可进一步表示为：
Figure FDA00032638826300000614
8.根据权利要求7所述的一种含菲结构的有机电致发光材料，其特征在于：所述式1选自下述化合物：
Figure FDA0003263882630000071
Figure FDA0003263882630000081
Figure FDA0003263882630000091
Figure FDA0003263882630000101
9.一种有机电致发光器件，主要包括阴极、阳极和两电极之间的有机层，或者主要包括出光层、阴极、阳极和两电极之间的有机层，其特征在于：所述两电极之间的有机层包含权利要求1-8任一所述的含菲结构的有机电致发光材料。
10.根据权利要求9所述的有机电致发光器件，其特征在于，所述两电极之间的有机层包括发光层，所述发光层由发光主体和发光客体组成，所述发光主体或发光客体包含权利要求1-8任一所述的含菲结构的有机电致发光材料。
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