CN114573639A - 含咔唑的oncn四齿配体的铂配合物 - Google Patents
含咔唑的oncn四齿配体的铂配合物 Download PDFInfo
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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Abstract
本发明涉及含咔唑的ONCN四齿配体的铂配合物,其结构如式(I)所示。该配合物具有明亮的绿光发射波长,可在OLED有机电致发光材料领域应用。本发明通过结构设计,能提高磷光材料的重原子效应,增强自旋耦合,能实现T1‑S0高效转化,从而得到高效的发光效率。同时ONCN四齿配体的铂配合物分子具有合成步骤简单,具有较多的可修饰位点。所含的咔唑基团增加的位阻,能有效降低分子间的聚集作用,避免形成激基复合物,进一步提高色纯度以及发光效率。
Description
技术领域
本发明涉及OLED材料领域,特别是涉及一种含咔唑的ONCN四齿配体的铂配合物。
背景技术
有机发光二极管(Organic Light-Emitting Diode,OLED)由美籍华裔教授邓青云(Ching W.Tang)于1979年在实验室中发现,因其具有自发光、广视角、几乎无穷高的对比度、较低耗电、极高反应速度以及潜在的柔性可折叠等优点,一直受到广泛的关注与研究。在OLED材料领域,磷光类OLED发光层掺杂材料发展较为迅速与成熟,其主要是基于一些重金属有机配合物。磷光材料在发光过程中可以充分利用单线态和三线态激子的能量,因此理论上其量子效率可达到100%,是目前业界使用比较广的发光材料。金属配合物发光材料已经在产业上实现了应用,传统的产业化磷光类OLED发光层掺杂材料以金属铱配合物为主,金属铂配合物因为其平面性导致的优异材料稳定性使得的近年来也得到了极大的发展,表现出赶超铱配合物的性质。具有更高效率和更长使用寿命的发光材料是目前产业界迫切的需要,ONCN四齿配体的铂配合物分子具有合成步骤简单,具有较多的可修饰位点,可改进空间极大。但在性能方面,如发光效率、使用寿命等仍须进一步提升。
发明内容
针对现有技术存在的上述问题,本发明提供了一类含ONCN四齿配体的铂配合物发光材料,该材料能提高磷光材料的重原子效应,从而提高在发光过程中对单线态和三线态激子的能量的利用率,从而提高发光效率。
该铂配合物应用于有机发光二极管中体现了良好的光电性能和器件寿命。
含咔唑的ONCN四齿配体的铂配合物,结构式如式(I)所示:
其中R1-R24独立的选自氢、氘、硫、卤素、羟基、酰基、含1-30个C原子的烷氧基、酰氧基、氨基、硝基、酰基氨基、氰基、羧基、苯乙烯基、氨基甲酰基、苄基羰基、芳氧基、二芳胺基、含1-30个C原子的饱和烷基、含2-20个C原子的不饱和烷基、含5-30个C原子的取代的或未取代的芳基、含5-30个C原子取代的或未取代的杂芳基、或者相邻R1-R24相互通过共价键连接成环,
Ar选自取代或未取代的具有6-30个碳原子的芳基、取代或未取代的具有3-30个碳原子的杂芳基;
所述取代为被氘、卤素、氨基、硝基、氰基或C1-C4烷基所取代。
优选的:其中R1-R24独立的选自氢、氘、硫、卤素、含1-10个C原子的烷氧基、氰基、苯乙烯基、芳氧基、二芳胺基、含1-10个C原子的饱和烷基、含2-8个C原子的不饱和烷基、含5-20个C原子取代的或未取代的芳基、含5-20个C原子取代的或未取代的杂芳基、或者相邻R1-R24相互通过共价键连接成环。
Ar选自取代或未取代的具有6-30个碳原子的2.3或3.4苯并芳基、取代或未取代的具有3-30个碳原子的2,3或3,4苯并杂芳基、取代或未取代的6-20个碳原子的苯连芳基、取代或未取代的6-20个碳原子的苯连杂芳基。
优选铂配合物的结构如下(II)、(III)式所示:
其中R1-R24独立的选自氢、氘、卤素、氰基、芳氧基、二芳胺基、含1-4个C原子的饱和烷基、含2-4个C原子的不饱和烷基、含5-10个C原子取代的或未取代的芳基、含5-10个C原子取代的或未取代的杂芳基、或者相邻R1-R24相互通过共价键连接成环。
A、B为5-30个C原子取代的或未取代的芳基、含5-30个C原子取代的或未取代的杂芳基。
进一步优选,通式(II)(III)中,R1至R24中R17和R19为叔丁基,其余为氢。
所述A、B为取代或未取代五元杂芳环、六元芳环、六元杂芳环或五元苯并杂芳环。
以下列出按照本发明的铂金属配合物,但不限于所列举的结构:
上述配合物的前体,结构如下式所示:
上述铂配合物的制备方法,以AR和BR偶联反应得到CR;CR酸性条件脱甲基反应得到DR;DR羟基卤代反应得到ER;ER与FR偶联反应得到GR的制备路线;
再将GR与卤代芳香衍生物偶联反应得到HR;HR酸性条件脱甲基得到IR;最后IR与金属铂产生ONCN四齿配位反应得到JR类型发光材料,
本发明的铂配合物作为发光层的磷光掺杂材料在OLED中的应用。
本发明通过结构设计,提高磷光材料的重原子效应,增强自旋耦合,能实现T1-S0高效转化,从而得到高效的发光效率。同时ONCN四齿配体的铂配合物分子具有合成步骤简单,具有较多的可修饰位点。所含的咔唑基团增加的位阻,能有效降低分子间的聚集作用,避免形成激基复合物,进一步提高色纯度以及发光效率。
本发明中的有机金属配合物具有高荧光量子效率,良好的热稳定性及低淬灭常数,可以制造高发光效率的绿光OLED器件。
附图说明
图1本发明器件结构图。
具体实施方式
下面结合附图和实施例对本发明做进一步的限定。
实施例1:中间体G的合成
中间体C的合成
取1000ml三口瓶,投入A(10.0g,40mmol,1.0eq.)、B(11.7g,50mmol,1.25eq.)、Pd132(280mg,0.4mmol,1%eq.)、K2CO3(13.8g,100mmol,2.5eq.)和甲苯/乙醇/H2O(200/200/50ml),氮气保护,90℃搅拌反应12h。反应结束后,先旋干大部分反应液,加去离子水,二氯甲烷萃取三次,旋干拌硅胶过柱(Hex:EA=10:1)。最终得到棕色固体21.0g(产率94.2%)。氢谱数据如下:
1H NMR(400MHz,CDCl3)δ8.52(s,1H),8.31(d,J=5.2Hz,1H),8.16–8.07(m,2H),7.46(dd,J=9.1,2.6Hz,3H),7.31(s,1H),7.28(s,1H),7.20(dd,J=5.3,1.4Hz,1H),7.08(s,1H),4.03(s,3H).
中间体D的合成
取250ml单口瓶,投入C(2.0g,7.2mmol,1.0eq.)、吡啶盐酸盐(10g,质量比为5),o-DCB(2ml),
氮气保护,180℃反应3.5h。反应结束后,冷却至室温,加入水和二氯甲烷搅拌30min,分液,收集有机层,得到粗产物,采用Hex打浆得到黄色固体(2.0g,产率~100%)。
1H NMR(400MHz,DMSO)δ11.22(s,1H),8.15(dd,J=18.5,7.7Hz,2H),7.59–7.52(m,2H),7.46–7.36(m,2H),7.24(t,J=7.6Hz,1H),7.20–7.13(m,1H),6.67(d,J=1.2Hz,1H),6.52(dd,J=6.7,1.7Hz,1H).
中间体E的合成
取上述中间体D,加入POCl3(10mL)和O-DCB(1ml),氮气保护,100℃反应18h,反应结束后,冷却至室温。旋蒸部分POCl3呈黏黏的状态,然后加入冰水,搅拌彻底淬灭POCl3,然后用二氯甲烷萃取反应液,得到粗产物,采用Hex打浆得到黄色固体(2.0g,产率~100%)。氢谱数据如下:1H NMR(400MHz,CDCl3)δ8.59(s,1H),8.49(dd,J=5.1,0.6Hz,1H),8.14(dd,J=17.2,7.5Hz,2H),7.70–7.65(m,1H),7.55(dd,J=5.1,1.5Hz,1H),7.53–7.42(m,3H),7.35(t,J=7.6Hz,1H),7.32–7.27(m,1H).
中间体G的合成
取250ml单口瓶,投入E(6.0g,21.5mmol,1.0eq.)、F(13.5g,23.5mmol,1.1eq.)(该中间体F合成制备方法见专利CN110872325A),Pd2(dba)3(2.15g,10%eq.),X-phos(2.15g,20%eq.),K3PO4-3H2O(17g,3.0eq.)和甲苯/乙醇/H2O(100/60/40ml),氮气保护,110℃反应12h。反应结束后,冷却至室温。抽滤得到滤液,旋蒸去除甲苯/乙醇,然后在萃取反应液,合并DCM层,过硅胶柱分离(Hex/EA=5/1)得到棕白色固体8g(产率51.6%,纯度HPLC99.15%)。氢谱数据如下:1H NMR(400MHz,CDCl3)δ8.85(d,J=4.6Hz,1H),8.80(s,1H),8.68(s,1H),8.22(d,J=7.9Hz,1H),8.14(dd,J=13.8,8.3Hz,4H),8.05–7.99(m,2H),7.92(d,J=1.4Hz,1H),7.67–7.51(m,7H),7.43–7.36(m,4H),7.26(s,1H),7.06(dd,J=15.3,7.9Hz,2H),3.88(s,3H),1.42(s,18H).
实施例2:配合物2的合成
中间体2b的合成
在250ml三口瓶中,加入G(5.0g,1.0eq)、2-碘萘(5.50g,3.0eq)、Cu(230mg,0.5eq)、CuI(688mg,0.5eq)、1,10-菲啰啉(1.30g,1.0eq)及碳酸铯(7.06g,3.0eq),100ml无水二甲苯作反应溶剂,氮气保护,油浴温度160℃反应3d后冷却至室温,反应液以EA作淋洗剂直接抽滤除去无机盐后拌硅胶柱层析(层析液hex:EA=8:1),收集得到黄色荧光产物点3.8g。氢谱数据如下1H NMR(400MHz,CDCl3)δ8.30(dd,J=5.9,3.1Hz,1H),8.24(d,J=8.2Hz,2H),8.18(s,2H),8.07(d,J=4.1Hz,2H),7.89(s,1H),7.59(t,J=5.1Hz,6H),7.48(d,J=8.6Hz,2H),7.45–7.30(m,8H),7.29(s,1H),7.17(s,2H),7.06(dd,J=8.7,5.1Hz,3H),3.91(s,3H),1.43(s,18H).
中间体2c的合成
在100ml单口瓶中,加入148b(3.0g),吡啶盐酸盐(30.0g)及邻二氯苯(3.0ml),氮气保护,油浴温度200℃反应8h后冷却至室温。用大量水溶解并用DCM萃取三次,有机相旋干拌硅胶柱层析(层析液hex:EA=10:1),得淡黄色产物2.8g。氢谱数据如下1H NMR(400MHz,CDCl3)δ8.31–8.28(m,1H),8.23(d,J=7.2Hz,2H),8.06(s,1H),7.98(t,J=7.3Hz,3H),7.83(s,1H),7.62–7.53(m,6H),7.51–7.28(m,11H),7.22(s,2H),7.11(d,J=4.6Hz,1H),7.00(d,J=10.9Hz,2H),1.43(d,J=2.2Hz,18H).配合物2的合成
取250ml单口瓶,投入2c(100mg,0.124mmol)、K2PtCl4(70mg,0.167mmol)、18冠6醚(6mg,0.012mmol)和乙酸(5mL),氮气保护,130度反应48h。反应结束后,加入过量的去离子水,固体析出,抽滤,固体用二氯甲烷溶解,旋干拌硅胶过柱(Hex:DCM:EA=20:20:1)。过柱后产品用二氯甲烷:正己烷=1:4重结晶。得到红色固体80mg。氢谱数据如下1H NMR(400MHz,CDCl3)δ8.56(s,1H),8.35–8.27(m,2H),8.24(d,J=7.6Hz,1H),8.10(d,J=7.3Hz,1H),7.73(s,1H),7.63(d,J=11.9Hz,4H),7.52–7.45(m,4H),7.41(dd,J=17.2,5.8Hz,5H),7.38–7.32(m,3H),7.13(dd,J=15.0,9.3Hz,4H),6.99(dd,J=18.3,10.4Hz,3H),6.77(t,J=6.9Hz,1H),1.45(d,J=12.3Hz,18H).
实施例3:配合物19的合成
配合物19的合成
中间体19b的合成
取250ml三口瓶,投入中间体G((2.5g,3.61mmol)、20a(2.02g,7.22mmol)、Cu(115mg,1.81mmol)、CuI(345mg,1.81mmol)、CsCO3(3.53g,10.83mmol)、邻菲罗啉(651mg,3.61mmol)和二甲苯(50ml),氮气保护,160℃搅拌反应30h。反应结束后,直接抽滤,EA淋洗,旋干得到棕色固体,后用(Hex:EA=5:1)过硅胶柱,,得2.2g白色固体。氢谱数据如下:
1H NMR(400MHz,CDCl3)δ8.49(s,1H),8.42(d,J=4.9Hz,1H),8.27(dd,J=5.5,3.5Hz,1H),8.19(dd,J=14.2,7.7Hz,2H),8.01(d,J=6.4Hz,2H),7.90(d,J=7.7Hz,1H),7.84(d,J=1.1Hz,1H),7.57–7.47(m,4H),7.46(s,1H),7.38(ddd,J=22.4,10.0,5.3Hz,5H),7.28(d,J=8.1Hz,1H),7.22–7.07(m,9H),7.03(t,J=7.7Hz,2H),3.87(s,3H),1.40(s,18H).
中间体19c的合成
取500ml单口瓶,投入20b(3.8g,4.5mmol)、吡啶盐酸盐(38g)和3.8mL邻二氯苯,氮气保护,200度反应8h。反应结束后,用二氯甲烷萃取两次,旋干拌硅胶过柱(Hex:DCM:EA=15:15:1)。所得粗品用乙酸乙酯/甲醇重结晶。得到淡黄色固体2.9g。氢谱数据如下
1H NMR(400MHz,CDCl3)δ8.45(d,J=4.9Hz,1H),8.31(s,1H),8.28(dd,J=6.1,2.9Hz,1H),8.22(d,J=7.7Hz,1H),8.02(s,2H),7.95(d,J=7.1Hz,1H),7.86(d,J=7.8Hz,1H),7.77(s,1H),7.59(s,1H),7.56–7.48(m,3H),7.47–7.39(m,4H),7.33(dd,J=9.9,7.5Hz,4H),7.15(qd,J=13.8,7.0Hz,10H),6.97(t,J=7.3Hz,2H),1.42(s,18H).
配合物19的合成
取250ml单口瓶,投入20c(426mg,0.513mmol)、K2PtCl4(256mg,0.616mmol)、TBAB(16.5mg,0.051mmol)和乙酸(42.6mL),氮气保护,130度反应48h。反应结束后,加入过量的去离子水,固体析出,抽滤,固体用二氯甲烷溶解,旋干拌硅胶过柱(Hex:DCM:EA=20:20:1)。过柱后产品用二氯甲烷:正己烷=1:4重结晶。得到红色固体380mg。氢谱数据如下
1H NMR(400MHz,CDCl3)δ8.84(d,J=5.3Hz,1H),8.40–8.27(m,2H),8.23(d,J=7.5Hz,1H),8.13(d,J=7.3Hz,1H),7.72(d,J=1.6Hz,1H),7.64(dd,J=6.7,1.6Hz,3H),7.55–7.30(m,8H),7.24(d,J=1.9Hz,1H),7.20(t,J=7.4Hz,5H),7.15–7.01(m,4H),6.78(dt,J=8.3,6.0Hz,4H),1.47(s,18H).
实施例4:配合物20的合成
中间体20b的合成
取250ml三口瓶,投入中间体G((2.5g,3.61mmol)、20a(2.02g,7.22mmol)、Cu(115mg,1.81mmol)、CuI(345mg,1.81mmol)、CsCO3(3.53g,10.83mmol)、邻菲罗啉(651mg,3.61mmol)和二甲苯(50ml),氮气保护,160℃搅拌反应30h。反应结束后,直接抽滤,EA淋洗,旋干得到棕色固体,后用(Hex:EA=5:1)过硅胶柱,,得2.2g白色固体。氢谱数据如下:
1H NMR(400MHz,CDCl3)δ8.49(s,1H),8.42(d,J=4.9Hz,1H),8.27(dd,J=5.5,3.5Hz,1H),8.19(dd,J=14.2,7.7Hz,2H),8.01(d,J=6.4Hz,2H),7.90(d,J=7.7Hz,1H),7.84(d,J=1.1Hz,1H),7.57–7.47(m,4H),7.46(s,1H),7.38(ddd,J=22.4,10.0,5.3Hz,5H),7.28(d,J=8.1Hz,1H),7.22–7.07(m,9H),7.03(t,J=7.7Hz,2H),3.87(s,3H),1.40(s,18H).
中间体20c的合成
取500ml单口瓶,投入20b(3.8g,4.5mmol)、吡啶盐酸盐(38g)和3.8mL邻二氯苯,氮气保护,200度反应8h。反应结束后,用二氯甲烷萃取两次,旋干拌硅胶过柱(Hex:DCM:EA=15:15:1)。所得粗品用乙酸乙酯/甲醇重结晶。得到淡黄色固体2.9g。氢谱数据如下
1H NMR(400MHz,CDCl3)δ8.45(d,J=4.9Hz,1H),8.31(s,1H),8.28(dd,J=6.1,2.9Hz,1H),8.22(d,J=7.7Hz,1H),8.02(s,2H),7.95(d,J=7.1Hz,1H),7.86(d,J=7.8Hz,1H),7.77(s,1H),7.59(s,1H),7.56–7.48(m,3H),7.47–7.39(m,4H),7.33(dd,J=9.9,7.5Hz,4H),7.15(qd,J=13.8,7.0Hz,10H),6.97(t,J=7.3Hz,2H),1.42(s,18H).
配合物20的合成
取250ml单口瓶,投入20c(426mg,0.513mmol)、K2PtCl4(256mg,0.616mmol)、TBAB(16.5mg,0.051mmol)和乙酸(42.6mL),氮气保护,130度反应48h。反应结束后,加入过量的去离子水,固体析出,抽滤,固体用二氯甲烷溶解,旋干拌硅胶过柱(Hex:DCM:EA=20:20:1)。过柱后产品用二氯甲烷:正己烷=1:4重结晶。得到红色固体380mg。氢谱数据如下
1H NMR(400MHz,CDCl3)δ8.84(d,J=5.3Hz,1H),8.40–8.27(m,2H),8.23(d,J=7.5Hz,1H),8.13(d,J=7.3Hz,1H),7.72(d,J=1.6Hz,1H),7.64(dd,J=6.7,1.6Hz,3H),7.55–7.30(m,8H),7.24(d,J=1.9Hz,1H),7.20(t,J=7.4Hz,5H),7.15–7.01(m,4H),6.78(dt,J=8.3,6.0Hz,4H),1.47(s,18H).
化合物发光性质:
配合物 | 吸收光谱λ/nm | 发射光谱(二氯甲烷溶液)λ/nm |
配合物2 | 237.5,286.6,357.4 | 518 |
配合物19 | 243,285.5,381.3 | 517 |
配合物20 | 242,286.9,383 | 516.5 |
下面是本发明化合物的应用实例。
器件制备方式:
首先,将透明导电ITO玻璃基板10(上面带有阳极20)依次经:洗涤剂溶液和去离子水,乙醇,丙酮,去离子水洗净,再用氧等离子处理300秒。
然后,在ITO上蒸渡3nm厚的HATCN作为空穴注入层30。
然后,蒸渡化合物TAPC,形成50nm厚的空穴传输层40。
然后,在空穴传输层上蒸渡7nm厚的客体配合物(9%)与主体TCTA(91%)作为发光层50。
然后,在空穴传输层上蒸渡3nm厚的客体配合物(9%)与主体TCTA(91%)作为发光层60。
然后,在发光层上蒸渡50nm厚的TmPyPb作为空穴阻挡层70。
最后,蒸渡0.8nm LiF为电子注入层80和100nm Al作为器件阴极90。
器件中所述结构式
器件结果:
比较例1及比较例2中的有机电致发光器件在20mA/cm2电流密度下的器件性能列于表1:
表1
本发明中的有机金属配合物在保持了高量子效率的良好的同时,略微降低了器件的驱动电压,提高了发光效率。但是对比比较例的LT95,实施例器件寿命明显有着质的提升。该系列器件数据表明,此类含咔唑ONCN配合物做磷光发光配体材料时,可以制造出高发光效率的绿光OLED器件并且可以达到非常好的寿命。
上述多种实施方案仅作为示例,不用于限制本发明范围。在不偏离本发明精神的前提下,本发明中的多种材料和结构可以用其它材料和结构替代。应当理解,本领域的技术人员无需创造性的劳动就可以根据本发明的思路做出许多修改和变化。因此,技术人员在现有技术基础上通过分析、推理或者部分研究可以得到的技术方案,均应在本申请所限制的保护范围内。
Claims (10)
2.根据权利要求1所述的铂配合物,其中R1-R24独立的选自氢、氘、硫、卤素、含1-10个C原子的烷氧基、氰基、苯乙烯基、芳氧基、二芳胺基、含1-10个C原子的饱和烷基、含2-8个C原子的不饱和烷基、含5-20个C原子取代的或未取代的芳基、含5-20个C原子取代的或未取代的杂芳基、或者相邻R1-R24相互通过共价键连接成环。
3.根据权利要求2所述的铂配合物,Ar选自取代或未取代的具有6-30个碳原子的2,3或3,4苯并芳基、取代或未取代的具有3-30个碳原子的2,3或3,4苯并杂芳基、取代或未取代的6-20个碳原子的苯连芳基、取代或未取代的6-20个碳原子的苯连杂芳基。
5.根据权利要求4所述的铂配合物,其中R1至R24中R17和R19为叔丁基,其余为氢。
6.根据权利要求5所述的铂配合物,所述A、B为取代或未取代五元杂芳环、六元芳环、六元杂芳环或五元苯并杂芳环。
10.权利要求1-7任一铂配合物作为发光层的磷光掺杂材料在OLED中的应用。
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CN202011366647.8A CN114573639B (zh) | 2020-11-30 | 2020-11-30 | 含咔唑的oncn四齿配体的铂配合物 |
PCT/CN2021/125929 WO2022111174A1 (zh) | 2020-11-30 | 2021-10-24 | 含咔唑的oncn四齿配体的铂配合物 |
DE112021005031.1T DE112021005031T5 (de) | 2020-11-30 | 2021-10-24 | Platinkomplex eines tetradentalen oncn-liganden mit carbazol |
US18/038,680 US20240032414A1 (en) | 2020-11-30 | 2021-10-24 | Platinum complex having oncn tetradentate ligand and containing carbazole |
KR1020237016114A KR20230088418A (ko) | 2020-11-30 | 2021-10-24 | 카르바졸을 함유하는 oncn 4좌 리간드의 백금 착물 |
JP2023531690A JP2023551245A (ja) | 2020-11-30 | 2021-10-24 | カルバゾ-ルを含有するoncn四座配位子の白金錯体 |
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WO2023082896A1 (zh) * | 2021-11-10 | 2023-05-19 | 广东阿格蕾雅光电材料有限公司 | 高效二价铂配合物磷光OLEDs材料及其应用 |
WO2023082898A1 (zh) * | 2021-11-10 | 2023-05-19 | 广东阿格蕾雅光电材料有限公司 | 高色纯度的二价铂配合物 |
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DE112021005031T5 (de) | 2023-07-20 |
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