CN111574536B - 一种有机电致发光化合物及其制备方法和应用 - Google Patents
一种有机电致发光化合物及其制备方法和应用 Download PDFInfo
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005296 thioaryloxy group Chemical group 0.000 description 1
- 125000005404 thioheteroaryloxy group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
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Abstract
本发明提供了一种有机电致发光化合物及其制备方法和应用,所述有机电致发光化合物具有式I的结构;所述有机电致发光器件包括基板、第一电极、第二电极和插入在所述第一电极和第二电极之间的至少一层有机层,所述有机层中含有所述有机电致发光化合物中的任意一种或至少两种组合;所述有机电致发光化合物具有较高的发光效率以及较久的使用寿命。
Description
技术领域
本发明涉及有机电致发光技术领域,特别涉及一种有机电致发光化合物及其制备方法和应用。
背景技术
上世纪末LED技术进入汽车行业,为汽车照明设计带来了更多可行性,也在安全性和稳定性方面得到了提升。不过,LED作为点光源依然有它的局限性,比如它的灯光虽然有更好的穿透力、但对于行人和其他车辆乘员来说,也会存在晃眼、刺眼的情况。
如何能在灯光亮度、照明效果和安全性上找到更好的平衡点,OLED这种新技术成为了突破。OLED是一种有机半导体照明技术,作为一种平面光源,OLED可以做到发光更为均匀和柔和,而且由于这种灯光元件更加轻薄且具有可挠性,不发热的特性又决定了它不需要散热和导光结构,因此可以进一步缩小体积和厚度,在设计上可塑性更强。
但是,OLED器件的寿命不够长,尚不足以大规模商业化应用。其中,影响OLED器件寿命的重要因素是发光层材料,尤其是发光主体材料。
因此,开发一种能够用于OLED器件,且能提高OLED器件的寿命和发光效率的主体材料非常有必要。
发明内容
针对现有技术的不足,本发明的目的在于提供一种有机电致发光化合物及其制备方法和应用,该有机电致发光化合物具有较高的效率以及较久的寿命。为达此目的,本发明采用以下技术方案:
本发明的目的之一在于提供一种有机电致发光化合物,所述有机电致发光化合物具有式I的结构:
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10和R11各自独立地选自氢原子、氘原子、氚原子、氰基、卤素、羟基、硝基、氨基、取代或未取代的C1-C60的烷基、取代或未取代的C2-C60的烯基、取代或未取代的C2-C60的炔基、取代或未取代的C6-C60的芳基、取代或未取代的C3-C60的杂芳基、取代或未取代的C1-C60的烷氧基、取代或未取代的C1-C60的硫代烷氧基、取代或未取代的C6-C60的芳氧基、取代或未取代的C6-C60的硫代芳氧基、-NR18R19、-SiR20R21R22中的任意一种;R18和R19各自独立选自取代或未取代的C6-C60的芳基、取代或未取代的C3-C60的杂芳基中的任意一种;R20、R21和R22各自独立选自取代或未取代的C1-C60的烷基、取代或未取代的C6-C60的芳基、取代或未取代的C3-C60的杂芳基中的任意一种;R1、R2、R3、R4、R5、R6、R7、R8、R9、R10和R11中各基团彼此不连接或其中2-4个(例如2个、3个或4个)相邻的基团连接成环,所述环各自独立地选自C3-C7的饱和或部分不饱和的碳环、C3-C7的饱和或部分不饱和的碳杂环、C6-C60的芳环或C3-C30的芳杂环中的任意一种;其中部分不饱和指代的是:碳环或碳杂环中有双键,并且不具备芳香性,例如环戊烯、环己烯等;卤素包括氟、氯、溴、碘中;。
L选自单键、取代或未取代的C1-C30亚烷基、取代或未取代的C6-C30亚芳基、取代或未取代的C3-C30的亚杂芳基、取代或未取代的C3-C30亚环烷基中的任意一种;
L优选单键、取代或未取代的C6-C30亚芳基、取代或未取代的C3-C30的亚杂芳基;
L更优选单键、取代或未取代的C6-C30亚芳基;
Ar1选自取代或未取代的C6-C60的芳基、取代或未取代的C3-C60的杂芳基、取代或未取代的C6-C60的芳氧基、取代或未取代的C6-C60的芳香胺基、取代或未取代的C6-C60的硫代芳氧基、取代或未取代的C6-C60的芳硼基、取代或未取代的C6-C60的芳膦基、取代或未取代的C4-C60的杂芳氧基、取代或未取代的C4-C60的杂芳香胺基、取代或未取代的C4-C60的芳香-C4-C60的杂芳香胺基、取代或未取代的C4-C60的硫代杂芳氧基、取代或未取代的C4-C60的杂芳硼基、取代或未取代的C4-C60的杂芳膦基中的任意一种;
优选地,Ar1选自取代或未取代的C6-C60的芳基、取代或未取代的C3-C60的杂芳基、取代或未取代的C6-C60的芳氧基、取代或未取代的C6-C60的芳香胺基、取代或未取代的C6-C60的硫代芳氧基、取代或未取代的C4-C60的杂芳氧基、取代或未取代的C4-C60的杂芳香胺基、取代或未取代的C4-C60的硫代杂芳氧基中的任意一种,其中取代或未取代的C4-C60的杂芳香胺基优选取代或未取代的C4-C60的芳香-C4-C60的杂芳基氨基;
n1为0-2的整数,例如0、1或2;
如上述基团中含有杂原子时,所述杂原子选自O、S、N、P、B或Si中的任意一种或至少两种的组合;
如上述基团中含有取代基时,所述取代的基团选自氘原子、卤素、硝基、氰基或由氘原子、卤素、氰基或硝基中的一个或多个取代或未取代的C1-C4的烷基、取代或未取代的C1-C4的烷氧基、取代或未取代的C2-C4的烯基、取代或未取代的C6-C12的芳基、取代或未取代的C6-C12的芳氧基、取代或未取代的C6-C12的芳胺基、取代或未取代的C3-C12的杂芳基或取代或未取代的C3-C12的杂芳胺基中的任意一种。
优选地,如上述基团中含有取代基时,所述取代基选自氢原子、氘原子、卤素、硝基、C1-C4的烷基、卤素取代的C1-C4的烷基、氘取代的C1-C4的烷基、C1-C4的烷氧基、C1-C4的烯基、卤素取代的C1-C4的烯基、氘取代的C1-C4的烯基、C6-C12的芳基、C6-C12的芳氧基、C6-C12的芳胺基、卤素取代的C6-C12的芳基、氘取代的C6-C12的芳基、C3-C12的杂芳基、C3-C12的杂芳胺基、卤素取代的C3-C12的杂芳基或氘取代的C3-C12的杂芳基中的任意一种。
C1-C4可以是C2、C3。
C1-C10可以是C2、C3、C4、C5、C6、C7、C8、C9等。
C1-C30可以是C2、C5、C8、C10、C12、C15、C18、C20、C22、C25、C28等。
C1-C60可以是C2、C5、C8、C10、C12、C15、C18、C20、C22、C25、C28、C30、C32、C35、C38、C40、C42、C45、C48、C50、C52、C55、C58、C60等。
C2-C60可以是C3、C5、C8、C10、C12、C15、C18、C20、C22、C25、C28、C30、C32、C35、C38、C40、C42、C45、C48、C50、C52、C55、C58、C60等。
C3-C12可以是C4、C5、C6、C7、C8、C9、C10、C11等。
C3-C30可以是C4、C5、C8、C10、C12、C15、C18、C20、C22、C25、C28、C30等。
C3-C60可以是C4、C6、C8、C10、C12、C15、C18、C20、C22、C25、C28、C30、C32、C35、C38、C40、C42、C45、C48、C50、C52、C55、C58等。
C4-C60可以是C6、C8、C10、C12、C15、C18、C20、C22、C25、C28、C30、C32、C35、C38、C40、C42、C45、C48、C50、C52、C55、C58等。
C6-C12可以是C7、C8、C9、C10、C11等。
C6-C30可以是C7、C10、C4、C13、C15、C18、C20、C22、C15、C28等。
C6-C60可以是C8、C10、C12、C15、C18、C20、C22、C25、C28、C30、C32、C35、C38、C40、C42、C45、C48、C50、C52、C55、C58等。
本发明中芳基包括但不限于苯基、联苯基、联三苯基、萘基、联萘基、苯基萘基、萘基苯基、芴基、苯基芴基、苯并芴基、二苯并芴基、菲基、苯基菲基、蒽基、茚基、亚三苯基、芘基、并四苯基、苝基、屈基、稠四苯基、荧蒽基或螺联二芴基等。
本发明中杂芳基包括但不限于呋喃基、苯硫基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、异噻唑基、异噁唑基、噁唑基、噁二唑基、三嗪基、四嗪基、三唑基、四唑基、呋吖基、吡啶基、吡嗪基、嘧啶基、哒嗪基、苯并呋喃基、苯并噻吩基、异苯并呋喃基、二苯并呋喃基、二苯并噻吩基、苯并咪唑基、苯并噻唑基、苯并异噻唑基、苯并异噁唑基、苯并噁唑基、异吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、异喹啉基、噌啉基、喹唑啉基、喹喔啉基、咔唑基、吩噁嗪基、吩噻嗪基、菲啶基、苯并间二氧杂环戊烯基、二氢吖啶基等。
本发明中“2-4个相邻的基团连接成环”是指R1-R11中处于同一六元环或相邻六元环中相邻位置的2-4个取代基之间可以通过化学键相互连接成环,本发明对具体的连接成环方式不做限定,如下文涉及相同的描述时,具有相同的意义。
本发明提供的如式I所示结构的有机电致发光化合物作为有机电致发光器件的发光层主体材料,其中母环结构为一个大的共轭结构,具有优异的化学性能和物理性能,并且具有较强的富电子性,使得化合物具有较好的空穴传输性能,并具有较高的三线态能级,能够避免激子扩散至空穴传输层或电子传输层,因此该化合物用于有机电致发光器件中能够增加发光器件的发光效率以及使用寿命。
优选地,所述R1、R2、R3、R4、R5、R6、R7、R8、R9、R10和R11各自独立地选自为氢原子、氘原子、氚原子、氰基、卤素、羟基、硝基、氨基、取代或未取代的C1-C4的烷基、取代或未取代的C2-C4的烯基、取代或未取代的C2-C4的炔基、取代或未取代的C6-C20的芳基、取代或未取代的C3-C20的杂芳基、取代或未取代的C1-C4的烷氧基、取代或未取代的C1-C4的硫代烷氧基、取代或未取代的C6-C20的芳氧基、取代或未取代的C6-C20的硫代芳氧基、-NR18R19、-SiR20R21R22中的任意一种;R18和R19各自独立选自取代或未取代的C6-C20的芳基、取代或未取代的C3-C20的杂芳基中的任意一种;R20、R21和R22各自独立选自取代或未取代的C1-C20的烷基、取代或未取代的C6-C20的芳基、取代或未取代的C3-C20的杂芳基中的任意一种;R1、R2、R3、R4、R5、R6、R7、R8、R9、R10和R11中各基团彼此不连接或其中2-4个相邻的基团连接成环,所述环各自独立地选自C3-C7的饱和或部分不饱和的碳环、C3-C7的饱和或部分不饱和的碳杂环、C6-C60的芳环或C3-C30的芳杂环中的任意一种。
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R18、R19、R20、R21、R22中,所述取代的基团各自独立地具有与上述相同的限定范围。
优选地,所述有机电致发光化合物具有式II或式III的结构:
其中,R1、R2、R3、R4、R5、R6、R7、R8、R9、X1、X2、X3各自独立地具有与上述相同的限定范围;
R12、R13、R14和R15各自独立地选自氢原子、氘原子、氚原子、卤素、氰基、羟基、硝基、氨基、取代或未取代的C1-C60的烷基、取代或未取代的C2-C60的烯基、取代或未取代的C2-C60的炔基、取代或未取代的C6-C60的芳基、取代或未取代的C3-C60的杂芳基、取代或未取代的C1-C60的烷胺基、取代或未取代的C1-C60的烷氧基、取代或未取代的C1-C60的硫代烷氧基、取代或未取代的C6-C60的芳氧基、取代或未取代的C6-C60的硫代芳氧基、-NR18R19、-SiR20R21R22中的任意一种;R18和R19各自独立选自取代或未取代的C6-C20的芳基、取代或未取代的C3-C20的杂芳基;R20、R21、R22各自独立选自取代或未取代的C1-C20的烷基、取代或未取代的C6-C20的芳基、取代或未取代的C3-C20的杂芳基,所述取代的基团各自独立地具有与上述相同的限定范围。
优选地,所述有机电致发光化合物具有式IV或式V的结构:
其中,R1、R2、R3、R4、R7、R8、R9、R12、R13、R14、R15、X1、X2、X3各自独立地具有与上述相同的限定范围。
优选地,所述有机电致发光化合物具有式VI或式VII的结构:
其中,R1、R2、R7、R8、R9、R12、R13、R14、R15、X1、X2、X3各自独立地具有与上述相同的限定范围。
优选地,所述Ar1选自取代或未取代的C6-C60的芳基、取代或未取代的C3-C60的杂芳基、取代或未取代的C6-C60的芳香胺基、取代或未取代的C4-C60的杂芳香胺基中的任意一种。
其中,Q1、Q2和Q3各自独立地选自N或CR17;
n2为0-4的整数(例如0、1、2、3或4);
Ar2选自氢原子、氘原子、卤素、硝基、氰基、取代或未取代的C1-C4的烷基、取代或未取代的C2-C4的烯基、取代或未取代的C6-C30的芳基、取代或未取代的C3-C30的杂芳基中的任意一种;
R16和R17各自独立地选自氢原子、氘原子、氚原子、氰基、卤素、羟基、硝基、氨基、取代或未取代的C1-C4的烷基、取代或未取代的C2-C4的烯基、取代或未取代的C2-C4的炔基、取代或未取代的C6-C20的芳基、取代或未取代的C3-C20的杂芳基、取代或未取代的C1-C4的烷氧基、取代或未取代的C1-C4的硫代烷氧基、取代或未取代的C6-C20的芳氧基、取代或未取代的C6-C20的硫代芳氧基中的任意一种;任意相邻的两个R16基团彼此不连接或其中2-4个相邻的基团连接成环,所述环各自独立地选自C6-C20的芳环或C3-C20的芳杂环;
Ar2、R16和R17中,所述取代的基团各自独立地具有与上述相同的限定范围。
优选地,所述Q1、Q2和Q3中至少有一项为N。
优选地,n2为0-2的整数(例如0、1或2)。
优选地,所述L选自单键、亚苯基、亚联苯基或亚萘基中的任意一种。
优选地,所述n1为0或1。
本发明的目的之二在于提供一种如目的之一所述的有机电致发光化合物的制备方法。
当X1为N,有机电致发光化合物的制备方法包括如下步骤:
A1、将A和B发生偶联反应,得到中间体1’;
A2、将步骤A1得到的中间体1’发生关环反应,得到中间体2’;
A3、将步骤A2得到的中间体2’和C发生偶联反应,得到中间体3’;
A4、将步骤A3得到的中间体3’发生偶联关环反应,得到中间体4’;
A5、将步骤A4得到的中间体4’和D发生偶联反应,得到所述有机电致发光化合物;
X2-X4、L、Ar1、R1-R9和n1具有与上述相同的限定范围,X为卤素;
当X1不为N,有机电致发光化合物的制备方法包括如下步骤:
B1、将M和N发生偶联反应,得到中间体1;
B2、将步骤B1得到的中间体1发生偶联关环反应,得到中间体2;
B3、将步骤B2得到的中间体2和H反生偶联反应,得到中间体3;
B4、将步骤B3得到的中间体3发生偶联关环反应,得到所述有机电致发光化合物;
X1-X4和R1-R9均具有与上述相同的限定范围。
本发明的目的之三在于提供一种如目的之一所述的有机电致发光化合物的应用,所述有机电致发光化合物用作有机电致发光材料。
优选地,所述有机电致发光材料用作有机电致发光层的主体材料。
本发明的目的之四在于提供一种有机电致发光器件,所述有机电致发光器件包括第一电极、第二电极以及位于第一电极和第二电极之间的有机层,所述有机层包括目的之一所述的有机电致发光化合物中的任意一种或至少两种的组合;
优选地,所述有机层包括发光层,所述发光层包括主体材料和客体材料,所述主体材料包括目的之一所述的有机电致发光化合物中的任意一种或至少两种的组合;
优选地,所述有机层包括发光辅助层,所述发光辅助层包含目的之一所述的有机电致发光化合物中的任意一种或至少两种的组合。
在本发明中,有机层还包括空穴注入层、空穴传输层、电子传输层、电子注入层、空穴阻挡层、电子阻挡层、发光辅助层中的任意一种或至少两种的组合。
本发明的目的之五在于提供一种如目的之四所述的有机电致发光器件在显示装置或照明装置中的应用。
本发明的有机电致发光装置,可以生产显示器系统,例如智能手机、平板电脑、笔记本、PC、TV、或用于汽车的显示器系统;或发光系统,例如室外或室内发光系统。
相对于现有技术,本发明具有以下有益效果:
本发明提供的如式I所示结构的有机电致发光化合物作为有机电致发光器件的发光层主体材料,其中母环结构为吲哚并咔唑结构,其中吲哚上的氮通过五元杂环与咔唑上的苯环连接,所得化合物具有合适的三线态能级,能避免激子扩散的同时具有与客体材料相匹配的三线态能级,因此该化合物用于有机电致发光器件中能够增加发光器件的发光效率以及使用寿命。
附图说明
图1为实施例1提供的有机电致发光器件的结构示意图,其中,1为基板,2为阳极,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。
具体实施方式
下面通过具体实施方式来进一步说明本发明的技术方案。本领域技术人员应该明了,所述实施例仅仅是帮助理解本发明,不应视为对本发明的具体限制。
本发明所提供的化合物的合成方法属于常规方法,本领域的技术人员可以通过现有技术进行合成,示例性地,制备通式如下所示:
X1-X4和R1-R9均具有与上述相同的限定范围,其中inter指代的意义为中间体,如inter1为中间体1,其他有出现类似的写法,指代的意义均与此处相同;
X2-X4、L、Ar1、R1-R9和n1均具有与上述相同的限定范围,其中inter’指代的意义为中间体,如inter1’为中间体1’,其他有出现类似的写法,指代的意义均与此处相同。
本发明中未提到的合成方法的化合物的都是通过商业途径获得的原料产品。本发明中所用溶剂和试剂,例如碳酸钾、甲苯、四(三苯基膦)钯、甲苯、二氯甲烷、三乙氧基膦、二氯苯、醋酸钯、三叔丁基膦等化学试剂,均可以从国内化工产品市场购买,例如购买自国药集团试剂公司、TCI公司、上海毕得医药公司、百灵威试剂公司等。另外,本领域技术人员也可以通过公知方法合成。
本发明中的中间体和化合物的分析检测使用质谱仪(型号型号Orbitrap ID-XTribrid)和有机元素分析仪(型号PE2400Ⅱ)。
下面将以多个制备例为例来详述本发明的上述新化合物的具体制备方法,但本发明的制备方法并不限于这些制备例。
制备例1
(1)inter1-9的合成:取100毫升三颈瓶,并放入搅拌子与上接回流管,充入氮气,加入原料raw-1(2.11克,0.01mol),原料raw-2(3.49克,0.01mol),碳酸钾(0.012mol),四(三苯基膦)钯(0.5mmol),甲苯(35毫升),水(5毫升),氮气保护下,60摄氏度反应8小时,反应完成后冷却至室温,加入3毫升冰水淬灭,二氯甲烷(3×35毫升)萃取,所得到的萃取液依序加入硫酸镁干燥、过滤及旋干,粗产物以层析纯化(乙酸乙酯/正己烷,1/10(体积比)),得inter1-9(1.76克,产率48%)。
(2)Inter2-9的合成:取100毫升三颈瓶,并放入搅拌子与上接回流管,干燥后充入氮气,加入inter1-9(3.66克,0.01mol),三乙氧基膦(0.011mol),1,2-二氯苯(30毫升),然后180摄氏度加热反应9小时;反应完成后冷却至室温,反应体系经浓缩,粗产物以层析纯化(乙酸乙酯/己烷,1/10),得到inter2-9(2.30克,产率69%)。
(3)Inter3-9的合成:取100毫升三颈瓶,并放入搅拌子与上接回流管,充入氮气,加入原料inter2-9(3.34克,0.01mol),原料raw-3(2.12克,0.01mol),碳酸钾(0.012mol),四(三苯基膦)钯(0.5mmol),甲苯(35毫升),水(5毫升),氮气保护下,60摄氏度反应8小时,反应完成后冷却至室温,加入3毫升冰水淬灭,二氯甲烷(3×15毫升)萃取,所得到的萃取液依序加入硫酸镁干燥、过滤及旋干,粗产物以层析纯化(乙酸乙酯/正己烷,1/10(体积比)),得inter3-9(1.73克,产率41%)。
(4)Inter4-9的合成:取100毫升三颈瓶,并放入搅拌子与上接回流管,充入氮气,加入原料inter3-9(4.22克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(35毫升),80摄氏度反应12小时,反应后冷却至室温,反应体系过滤后浓缩,粗产物以层析纯化(二氯甲烷/己烷,1/10),得Inter4-9(1.66克,产率43%)。
(5)化合物6的合成:取100毫升三颈瓶,并放入搅拌子与上接回流管,充入氮气,加入原料inter4-9(3.86克,0.01mol),raw-5(3.43克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(50毫升),80摄氏度反应12小时,反应后冷却至室温,反应体系过滤后浓缩,粗产物以层析纯化(二氯甲烷/己烷,1/10),得化合物6(5.96克,产率86%)。
元素分析:C47H27N5S理论值:C,81.36,H,3.92,N,10.09,S,4.62;实测值:C,81.44,H,3.91,N,10.05,S,4.60;HRMS(ESI)m/z(M+):理论值:693.1987,实测值:693.1994。
制备例2
化合物9的合成:取100毫升三颈瓶,并放入搅拌子与上接回流管,充入氮气,加入原料inter4-9(3.86克,0.01mol),raw-4(2.40克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(35毫升),80摄氏度反应12小时,反应后冷却至室温,反应体系过滤后浓缩,粗产物以层析纯化(二氯甲烷/己烷,1/10),得化合物9(4.84克,产率82%)。
元素分析:C40H22N4S理论值:C,81.33,H,3.75,N,9.48,S,5.43;实测值:C,81.27,H,3.76,N,9.52,S,5.45;HRMS(ESI)m/z(M+):理论值:590.1565,实测值:590.1573。
制备例3
(1)inter1-74的合成:原料raw-6(3.11克,0.01mol),原料raw-2(3.49克,0.01mol),碳酸钾(0.012mol),四(三苯基膦)钯(0.5mmol),甲苯(35毫升),水(3毫升),其余条件同inter1-9的合成,得inter1-74(2.38克,产率51%)。
(2)Inter2-74的合成:inter1-74(4.66克,0.01mol),三乙氧基膦(0.011mol),1,2-二氯苯(30毫升),其余条件同inter2-9的合成,得Inter2-74(3.17克,产率73%)。
(3)Inter3-74的合成:inter2-74(4.34克,0.01mol),原料raw-3(2.12克,0.01mol),碳酸钾(0.012mol),四(三苯基膦)钯(0.5mmol),甲苯(35毫升),水(5毫升),其余条件同inter3-9的合成,得Inter3-74(2.09克,产率40%)。
(4)Inter4-74的合成:inter3-74(5.22克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(30毫升),其余条件同Inter4-9的合成,得Inter4-74(2.24克,产率46%)。
(5)化合物74的合成:inter4-74(4.86克,0.01mol),raw-7(3.16克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(35毫升),其余条件同pro-9的合成,得化合物74(6.20克,产率81%)。
元素分析:C54H30N4S理论值:C,84.57,H,3.94,N,7.31,S,4.18;实测值:C,84.63,H,3.93,N,7.28,S,4.16;HRMS(ESI)m/z(M+):理论值:766.2191,实测值:766.2198。
制备例4
(1)inter1-164的合成:原料raw-8(3.01克,0.01mol),原料raw-2(3.49克,0.01mol),碳酸钾(0.012mol),四(三苯基膦)钯(0.5mmol),甲苯(35毫升),水(5毫升),其余条件同inter1-9的合成,得inter1-164(2.10克,产率46%)。
(2)Inter2-164的合成:inter1-164(4.56克,0.01mol),三乙氧基膦(0.011mol),1,2-二氯苯(35毫升),其余条件同inter2-9的合成,得Inter2-164(3.05克,产率72%)。
(3)Inter3-164的合成:inter2-164(4.24克,0.01mol),原料raw-9(1.96克,0.01mol),碳酸钾(0.012mol),四(三苯基膦)钯(0.5mmol),甲苯(35毫升),水(5毫升),其余条件同inter3-9的合成,得Inter3-164(1.98克,产率40%)。
(4)Inter4-164的合成:inter3-164(4.96克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(30毫升),其余条件同Inter4-9的合成,得Inter4-164(1.89克,产率41%)。
(5)化合物164的合成:inter4-164(4.60克,0.01mol),raw-10(3.43克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(40毫升),其余条件同pro-9的合成,得化合物164(6.37克,产率83%)。
元素分析:C53H29N5O2理论值:C,82.90,H,3.81,N,9.12;实测值:C,82.87,H,3.82,N,9.15;HRMS(ESI)m/z(M+):理论值:767.2321,实测值:767.2328。
制备例5
(1)inter1-173的合成:原料raw-11(2.88克,0.01mol),原料raw-2(3.49克,0.01mol),碳酸钾(0.012mol),四(三苯基膦)钯(0.5mmol),甲苯(35毫升),水(5毫升),其余条件同inter1-9的合成,得inter1-173(2.08克,产率47%)。
(2)Inter2-173的合成:inter1-173(4.43克,0.01mol),三乙氧基膦(0.011mol),1,2-二氯苯(35毫升),其余条件同inter2-9的合成,得Inter2-173(2.96克,产率72%)。
(3)Inter3-173的合成:inter2-173(4.11克,0.01mol),原料raw-3(2.12克,0.01mol),碳酸钾(0.012mol),四(三苯基膦)钯(0.5mmol),甲苯(35毫升),水(5毫升),其余条件同inter3-9的合成,得Inter3-173(1.84克,产率38%)。
(4)Inter4-173的合成:inter3-173(4.83克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(35毫升),其余条件同Inter4-9的合成,得Inter4-173(1.97克,产率44%)。
(5)化合物173的合成:inter4-173(4.47克,0.01mol),raw-12(2.67克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(40毫升),其余条件同pro-9的合成,得化合物173(5.70克,产率84%)。
元素分析:C46H26N6O理论值:C,81.40,H,3.86,N,12.38;实测值:C,81.46,H,3.85,N,12.34;HRMS(ESI)m/z(M+):理论值:678.2168,实测值:678.2172。
制备例6
(1)Inter1-62的合成:取100毫升三颈瓶,并放入搅拌子与上接回流管,充入氮气,加入原料raw-13(3.12克,0.01mol),1-氯-2-苯胺(1.27克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(35毫升),80摄氏度反应12小时,反应后冷却至室温,反应体系过滤后浓缩,粗产物以层析纯化(二氯甲烷/己烷,1/10),得Inter1-62(1.44克,产率40%)。
(2)Inter2-62的合成:取100毫升三颈瓶,并放入搅拌子与上接回流管,干燥后充入氮气,Inter1-62(3.59克,0.1mol),二氯二(三环己基膦)钯(PdCl2(PCy3)2,5mmol)、特戊酸(t-BuCO2H,0.2mol)、碳酸铯(Cs2CO3,0.2mol)和二甲基乙酰胺(30毫升),120摄氏度下搅拌10小时,反应完成后冷却至室温,反应体系经浓缩,粗产物以层析纯化(乙酸乙酯/己烷,1/10),得到Inter2-62(1.52克,产率47%)。
(3)Inter3-62的合成:取100毫升三颈瓶,并放入搅拌子与上接回流管,充入氮气,加入原料inter2-62(3.23克,0.01mol),raw14(2.29克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(45毫升),80摄氏度反应12小时,反应后冷却至室温,反应体系过滤后浓缩,粗产物以层析纯化(二氯甲烷/己烷,1/10),得Inter3-62(2.12克,产率45%)。
(4)Inter4-62的合成:取100毫升三颈瓶,并放入搅拌子与上接回流管,干燥后充入氮气,Inter3-62(4.72克,0.1mol),二氯二(三环己基膦)钯(PdCl2(PCy3)2,5mmol)、特戊酸(t-BuCO2H,0.2mol)、碳酸铯(Cs2CO3,0.2mol)和二甲基乙酰胺(30毫升),120摄氏度下搅拌10小时,反应完成后冷却至室温,反应体系经浓缩,粗产物以层析纯化(乙酸乙酯/己烷,1/10),得到Inter4-62(1.92克,产率44%)。
(5)62的合成:取100毫升三颈瓶,并放入搅拌子与上接回流管,充入氮气,加入原料Inter4-62(4.36克,0.01mol),raw-15(3.16克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),碳酸钾(0.012mol),甲苯(45毫升),80摄氏度反应12小时,反应后冷却至室温,反应体系过滤后浓缩,粗产物以层析纯化(二氯甲烷/己烷,1/10),得化合物62(5.58克,产率78%)。
元素分析:C50H28N4S理论值:C,83.77,H,3.94,N,7.82,S,4.47;实测值:C,83.82,H,3.93,N,7.80,S,4.45;HRMS(ESI)m/z(M+):理论值:716.2035,实测值:716.2041。
制备例7
(1)Inter1-156的合成:raw-16(4.10克,0.01mol),1-氯-2-苯胺(1.27克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(45毫升),其余条件同Inter1-62,得Inter1-156(1.69克,产率37%)。
(2)Inter2-156的合成:Inter1-156(4.57克,0.1mol),二氯二(三环己基膦)钯(PdCl2(PCy3)2,5mmol)、特戊酸(t-BuCO2H,0.2mol)、碳酸铯(Cs2CO3,0.2mol)和二甲基乙酰胺(40毫升),其余条件同Inter2-62的合成,得Inter2-156(1.81克,产率43%)。
(3)Inter3-156的合成:inter2-156(4.21克,0.01mol),raw14(2.29克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(45毫升),其余条件同Inter3-62的合成,得Inter3-156(2.34克,产率41%)。
(4)Inter4-156的合成:Inter3-156(5.70克,0.1mol),二氯二(三环己基膦)钯(PdCl2(PCy3)2,5mmol)、特戊酸(t-BuCO2H,0.2mol)、碳酸铯(Cs2CO3,0.2mol)和二甲基乙酰胺(40毫升),其余条件同Inter4-62的合成,得Inter4-156(2.40克,产率45%)。
(5)156的合成:Inter4-156(5.34克,0.01mol),raw-17(3.16克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),碳酸钾(0.012mol),甲苯(45毫升),其余条件同pro-6的合同,得156(6.76克,产率83%)。
元素分析:C59H34N4O理论值:C,86.96,H,4.21,N,6.88;实测值:C,86.92,H,4.22,N,6.91;HRMS(ESI)m/z(M+):理论值:814.2733,实测值:814.2741。
制备例8
(1)Inter1-196的合成:raw-18(2.46克,0.01mol),1-氯-2-苯胺(1.27克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(35毫升),其余条件同Inter1-62,得Inter1-196(1.11克,产率38%)。
(2)Inter2-196的合成:Inter1-196(2.93克,0.01mol),二氯二(三环己基膦)钯(PdCl2(PCy3)2,0.5mmol)、特戊酸(t-BuCO2H,0.02mol)、碳酸铯(Cs2CO3,0.02mol)和二甲基乙酰胺(30毫升),其余条件同Inter2-62的合成,得Inter2-196(1.13克,产率44%)。
(3)Inter3-196的合成:inter2-196(2.57克,0.01mol),raw14(2.29克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(30毫升),其余条件同Inter3-62的合成,得Inter3-196(1.58克,产率39%)。
(4)Inter4-196的合成:Inter3-196(4.06克,0.01mol),二氯二(三环己基膦)钯(PdCl2(PCy3)2,0.5mmol)、特戊酸(t-BuCO2H,0.02mol)、碳酸铯(Cs2CO3,0.02mol)和二甲基乙酰胺(40毫升),其余条件同Inter4-62的合成,得Inter4-196(1.52克,产率41%)。
(5)196的合成:Inter4-196(3.70克,0.01mol),raw-10(3.43克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),碳酸钾(0.012mol),甲苯(45毫升),其余条件同pro-6的合同,得196(5.62克,产率83%)。
元素分析:C47H27N5O理论值:C,83.29,H,4.02,N,10.33;实测值:C,83.34,H,4.01,N,10.29;HRMS(ESI)m/z(M+):理论值:677.2216,实测值:677.2221。
制备例9
(1)Inter1-219的合成:raw-19(2.72克,0.01mol),1-氯-2-苯胺(1.27克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(35毫升),其余条件同Inter1-62,得Inter1-219(1.18克,产率37%)。
(2)Inter2-219的合成:Inter1-219(3.19克,0.01mol),二氯二(三环己基膦)钯(PdCl2(PCy3)2,0.5mmol)、特戊酸(t-BuCO2H,0.02mol)、碳酸铯(Cs2CO3,0.02mol)和二甲基乙酰胺(30毫升),其余条件同Inter2-62的合成,得Inter2-219(1.25克,产率44%)。
(3)Inter3-219的合成:inter2-219(2.83克,0.01mol),raw14(2.29克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(35毫升),其余条件同Inter3-62的合成,得Inter3-219(1.60克,产率37%)。
(4)Inter4-219的合成:Inter3-219(4.32克,0.01mol),二氯二(三环己基膦)钯(PdCl2(PCy3)2,0.5mmol)、特戊酸(t-BuCO2H,0.02mol)、碳酸铯(Cs2CO3,0.02mol)和二甲基乙酰胺(30毫升),其余条件同Inter4-62的合成,得Inter4-219(1.50克,产率38%)。
(5)219的合成:Inter4-219(3.96克,0.01mol),raw-20(1.88克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),碳酸钾(0.012mol),甲苯(35毫升),其余条件同pro-6的合同,得219(4.71克,产率86%)。
元素分析:C41H28N2理论值:C,89.75,H,5.14,N,5.11;实测值:C,89.79,H,5.12,N,5.09;HRMS(ESI)m/z(M+):理论值:548.2252,实测值:548.2260。
制备例10
(1)Inter1-278的合成:raw-21(3.94克,0.01mol),1-氯-2-苯胺(1.27克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(35毫升),其余条件同Inter1-62,得Inter1-278(1.50克,产率34%)。
(2)Inter2-278的合成:Inter1-278(4.41克,0.01mol),二氯二(三环己基膦)钯(PdCl2(PCy3)2,0.5mmol)、特戊酸(t-BuCO2H,0.02mol)、碳酸铯(Cs2CO3,0.02mol)和二甲基乙酰胺(40毫升),其余条件同Inter2-62的合成,得Inter2-278(1.70克,产率42%)。
(3)Inter3-278的合成:inter2-278(4.05克,0.01mol),raw14(2.29克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(45毫升),其余条件同Inter3-62的合成,得Inter3-278(2.16克,产率39%)。
(4)Inter4-278的合成:Inter3-278(5.54克,0.01mol),二氯二(三环己基膦)钯(PdCl2(PCy3)2,0.5mmol)、特戊酸(t-BuCO2H,0.02mol)、碳酸铯(Cs2CO3,0.02mol)和二甲基乙酰胺(40毫升),其余条件同Inter4-62的合成,得Inter4-278(1.76克,产率34%)。
(5)278的合成:Inter4-278(5.18克,0.01mol),raw-22(2.79克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),碳酸钾(0.012mol),甲苯(45毫升),其余条件同pro-6的合同,得278(6.47克,产率85%)。
元素分析:C57H35N3理论值:C,89.85,H,4.63,N,5.52;实测值:C,89.88,H,4.62,N,5.50;HRMS(ESI)m/z(M+):理论值:761.2831,实测值:761.2838。
制备例11
(1)Inter1-313的合成:inter2-9(3.34克,0.01mol),原料raw-23(1.62克,0.01mol),碳酸钾(0.012mol),四(三苯基膦)钯(0.5mmol),甲苯(35毫升),水(5毫升),其余条件同inter3-9的合成,得Inter1-313(1.38克,产率37%)。
(2)Inter2-313的合成:inter1-313(3.72克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(45毫升),其余条件同Inter4-9的合成,得Inter2-313(1.61克,产率48%)。
(3)化合物313的合成:inter2-313(3.36克,0.01mol),raw-24(3.16克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(45毫升),其余条件同pro-9的合成,得化合物313(5.05克,产率82%)。
元素分析:C42H24N4S理论值:C,81.79,H,3.92,N,9.08,S,5.20;实测值:C,81.84,H,3.91,N,9.06,S,5.19;HRMS(ESI)m/z(M+):理论值:616.1722,实测值:616.1728。
制备例12
(1)Inter1-327的合成:inter2-9(3.34克,0.01mol),原料raw-25(2.34克,0.01mol),碳酸钾(0.012mol),四(三苯基膦)钯(0.5mmol),甲苯(35毫升),水(5毫升),其余条件同inter3-9的合成,得Inter1-327(1.42克,产率32%)。
(2)Inter2-327的合成:inter1-327(4.44克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(45毫升),其余条件同Inter4-9的合成,得Inter2-327(1.96克,产率48%)。
(3)化合物327的合成:inter2-327(4.08克,0.01mol),raw-12(2.67克,0.01mol),醋酸钯(0.5mmol),三叔丁基膦(0.5mmol),叔丁醇钠(0.01mol),甲苯(45毫升),其余条件同pro-9的合成,得化合物327(5.62克,产率88%)。
元素分析:C40H29N5SSi理论值:C,75.09,H,4.57,N,10.95,S,5.01;实测值:C,75.15,H,4.56,N,10.92,S,4.99;HRMS(ESI)m/z(M+):理论值:639.1913,实测值:639.1922。
实施例1
本实施例提供一种有机电致发光器件,结构示意图如图1所示,包括自下而上依次设置在基板1上的阳极层2、空穴注入层3、空穴传输层4、发光层5、电子传输层6、电子注入层7和阴极8。
其中,阳极2选用ITO材料,空穴注入层3选用PD和NPB,其中,HAT(CN)6:NPB=3:97(质量比);空穴传输层4选用NPB;发光层5由主体材料和掺杂材料组成,主体材料选用合成例1合成的化合物6,客体材料选用Ir(DBQ)2(acac),主体材料和客体材料的质量比为95:5;电子传输层6选用BPhen和LiQ,其中BPhen:LiQ=1:1(质量比);电子注入层7选用LiQ;阴极8选用Mg/Ag,其中,Mg:Ag=9:1(质量比)。
有机电致发光器件的制备过程如下:
(1)基板清理:将涂布了透明ITO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,在上述阳极层膜上以共蒸的方式真空蒸镀空穴注入材料,PD与NPB按质量比调整速率,蒸镀总速率为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80nm;
(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,主体材料与客体材料按质量比调整蒸镀速率,蒸镀总速率为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,按质量比调整蒸镀速率,其蒸镀总速率为0.1nm/s,蒸镀总膜厚为30nm;
(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)Mg/Ag作为器件的阴极层,按质量比调整蒸镀速率,蒸镀总速率为0.1nm/s,蒸镀总膜厚为80nm。
实施例2-9
与实施例1的区别仅在于将实施例1中的化合物6替换为制备例2-8以及制备例12的化合物,其余组成以及制备方法均与实施例1相同。
对比例1
与实施例1的区别仅在于将实施例1中的化合物6替换为C-1,其余组成以及制备方法均与实施例1相同。
实施例10
与实施例1的区别仅在于,发光层的主体材料采用6,并在空穴传输层和发光层之间加入发光辅助层,发光辅助层采用的材料为278(制备例10制备的化合物),厚度为5mm。
将具体实施方式中的化合物进行如下性能测试:
(1)使用热重分析仪(美国TA TGA55)对有机电致发光化合物材料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%的温度定义为热分解温度(Td),测定结果如表1所示:
表1
制备例 | 化合物 | T<sub>d</sub>(℃) | 制备例 | 化合物 | T<sub>d</sub>(℃) |
制备例1 | 6 | 396 | 制备例7 | 156 | 468 |
制备例2 | 9 | 331 | 制备例8 | 196 | 383 |
制备例3 | 74 | 430 | 制备例9 | 219 | 302 |
制备例4 | 164 | 427 | 制备例10 | 278 | 428 |
制备例5 | 173 | 380 | 制备例11 | 313 | 347 |
制备例6 | 62 | 403 | 制备例12 | 327 | 361 |
由表1可知,本发明所述化合物的热稳定性高,其热分解温度可达331-468℃,避免材料在制备、封装等过程中发生分解,提高器件的稳定性。
(2)测试HOMO和LOMO能级:使用电化学工作站利用循环伏安法(CV上海辰华CHI-600E)对制备例得到的有机电致化合物材料的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:
HOMO能阶=-e(Eox-E1/2,ferrocene)+(-4.8)eV
LUMO能阶=-e(Ere-E1/2,ferrocene)+(-4.8)eV
ET1(eV)三线态能级。
Eox为氧化电位,Ere为还原电位,E1/2,ferrocene为二茂铁电位。三线态能级测试条件:荧光分光光度计(日立F-4600),溶液状态(甲苯做溶剂,浓度2*10-5mol/L),-78摄氏度条件下测试。
ET1=1240/最短吸收波长
测试结果见表2:
表2
由表2可知,本发明所述化合物具有合适的HOMO、LUMO能级,以及三线态能级,化合物的HOMO能级和LUMO能级与相邻的传输层相匹配,用作有机电致发光材料能有效降低驱动电压,提高发光效率。
(3)针对本发明提供的部分器件实施例和1个器件对比例中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PR 650光谱扫描亮度计和KeithleyK 2400数字源表系统同步测试,测试条件:电流密度为20mA/cm2,室温;
寿命测试:器件亮度下降至原始亮度的98%时记录时间(以小时计)。
结果见表3。
表3
由表3可知,本发明化合物用作发光层材料,或辅助发光层材料,具有低驱动电压和改进的电流效率和使用寿命,其驱动电压低至4.44-4.58V,电流效率可达23-27cd/A,工作寿命可达80-121h;由此可见,本发明提供的有机电致化合物作为发光层或者辅助发光层时,可以有效降低器件的工作电压,同时提升器件的发光效率以及使用寿命。
申请人声明,以上所述仅为本发明的具体实施方式,但本发明的保护范围并不局限于此,所属技术领域的技术人员应该明了,任何属于本技术领域的技术人员在本发明揭露的技术范围内,可轻易想到的变化或替换,均落在本发明的保护范围和公开范围之内。
Claims (19)
1.一种有机电致发光化合物,其特征在于,所述有机电致发光化合物具有式I的结构:
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10和R11各自独立地选自氢原子、氘原子、氚原子、氰基、卤素、羟基、硝基、氨基、取代或未取代的C1-C4的烷基、取代或未取代的C2-C4的烯基、取代或未取代的C6-C20的芳基、取代或未取代的C3-C20的杂芳基、取代或未取代的C1-C4的烷氧基、-NR18R19、-SiR20R21R22中的任意一种;R18和R19各自独立选自取代或未取代的C6-C20的芳基、取代或未取代的C3-C20的杂芳基中的任意一种;R20、R21和R22各自独立选自取代或未取代的C1-C4的烷基、取代或未取代的C6-C20的芳基、取代或未取代的C3-C20的杂芳基中的任意一种;
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10和R11中各基团彼此不连接或其中2-4个相邻的基团连接成环,所述环各自独立地选自C6-C30的芳环或C3-C30的芳杂环中的任意一种;
L选自单键、亚苯基、亚联苯基或亚萘基中的任意一种;
Q1、Q2和Q3各自独立地选自N或CR17;
Ar2独立地选自氢原子、氘原子、卤素、硝基、氰基、取代或未取代的C1-C4的烷基、取代或未取代的C2-C4的烯基、取代或未取代的C6-C30的芳基、取代或未取代的C3-C30的杂芳基中的任意一种;
n2为0-2的整数;
R16和R17各自独立地选自氢原子、氘原子、氚原子、氰基、卤素、羟基、硝基、氨基、取代或未取代的C1-C4的烷基、取代或未取代的C2-C4的烯基、取代或未取代的C6-C20的芳基、取代或未取代的C3-C20的杂芳基、取代或未取代的C1-C4的烷氧基中的任意一种;任意相邻的两个R16基团彼此不连接或其中2-4个相邻的基团连接成环,所述环各自独立地选自C6-C20的芳环或C3-C20的芳杂环;
n1为1;
Ar1、R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R18、R19、R20、R21、R22中,所述取代的基团选自氘原子、卤素、硝基、氰基或由氘原子、卤素、氰基或硝基中的一个或多个取代或未取代的C1-C4的烷基、取代或未取代的C1-C4的烷氧基、取代或未取代的C2-C4的烯基、取代或未取代的C6-C12的芳基、取代或未取代的C6-C12的芳胺基、取代或未取代的C3-C12的杂芳基、取代或未取代的C3-C12的杂芳胺基中的任意一种。
2.根据权利要求1所述的有机电致发光化合物,其特征在于,所述R1、R2、R3、R4、R5、R6、R7、R8、R9、R10和R11各自独立地选自为氢原子、氘原子、氰基、卤素、取代或未取代的C1-C4的烷基、取代或未取代的C6-C20的芳基、取代或未取代的C3-C20的杂芳基、取代或未取代的C1-C4的烷氧基、-NR18R19中的任意一种;R18、R19各自独立选自取代或未取代的C6-C20的芳基、取代或未取代的C3-C20的杂芳基中的任意一种;
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10和R11中各基团彼此不连接或其中2-4个相邻的基团连接成环,所述环各自独立地选自C6-C20的芳环或C3-C20的芳杂环中的任意一种;
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R18、R19中,所述取代的基团各自独立地具有与权利要求1相同的限定范围。
6.根据权利要求1所述的有机电致发光化合物,其特征在于,所述Q1、Q2和Q3中至少有一项为N。
A1、将A和B发生偶联反应,得到中间体1’;
A2、将步骤A1得到的中间体1’发生关环反应,得到中间体2’;
A3、将步骤A2得到的中间体2’和C发生偶联反应,得到中间体3’;
A4、将步骤A3得到的中间体3’发生偶联关环反应,得到中间体4’;
A5、将步骤A4得到的中间体4’和D发生偶联反应,得到所述有机电致发光化合物;
X2-X4、L、Ar1、R1-R9和n1具有与权利要求1-11任一项相同的限定范围,X为卤素。
14.一种根据权利要求1-11中任一项所述的有机电致发光化合物的应用,其特征在于,所述有机电致发光化合物用作有机电致发光材料。
15.根据权利要求14所述的有机电致发光化合物的应用,其特征在于,所述有机电致发光材料用作有机电致发光层的主体材料。
16.一种有机电致发光器件,其特征在于,所述有机电致发光器件包括第一电极、第二电极以及位于第一电极和第二电极之间的有机层,所述有机层包括权利要求1-11任一项所述的有机电致发光化合物中的任意一种或至少两种的组合。
17.根据权利要求16所述的有机电致发光器件,其特征在于,所述有机层包括发光层,所述发光层包括主体材料和客体材料,所述主体材料包括权利要求1-11任一项所述的有机电致发光化合物中的任意一种或至少两种的组合。
18.根据权利要求16所述的有机电致发光器件,其特征在于,所述有机层包括发光辅助层,所述发光辅助层包含权利要求1-11任一项所述的有机电致发光化合物中的任意一种或至少两种的组合。
19.根据权利要求16-18任一项所述的有机电致发光器件在显示装置或照明装置中的应用。
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