CN112979709A - 一种金属配合物及其应用 - Google Patents
一种金属配合物及其应用 Download PDFInfo
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- CN112979709A CN112979709A CN201911291180.2A CN201911291180A CN112979709A CN 112979709 A CN112979709 A CN 112979709A CN 201911291180 A CN201911291180 A CN 201911291180A CN 112979709 A CN112979709 A CN 112979709A
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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Abstract
Description
技术领域
本发明涉及有机电致发光材料领域,具体涉及一种金属配合物及其作为发光材料在有机电致发光器件上的应用。
背景技术
有机光电子器件,包括但不限于以下几类:有机电致发光器件(OLEDs),有机薄膜晶体管(OTFTs),有机光伏器件(OPVs),发光电化学池(LCEs)和化学传感器。
近年来,OLEDs作为一种有巨大应用前景的照明、显示技术,受到了学术界与产业界的广泛关注。OLEDs器件具有自发光、广视角、反应时间短及可制备柔性器件等特性,成为下一代显示、照明技术的有力竞争者。但目前OLEDs仍然存在效率低、寿命短等问题,有待人们进一步研究。
早期的荧光OLEDs通常只能利用单重态发光,器件中所产生的三重态激子无法有效利用而通过非辐射的方式回到基态。因此,荧光OLEDs的量子产率较低,限制了OLEDs的推广使用。1998年,香港大学支志明等人首次报道了电致磷光现象。同年,Thompson等人使用过渡金属配合物作为发光材料制备了磷光OLEDs。磷光OLEDs能够同时利用单线态和三线态激子发光,实现100%的内量子效率,在很大程度上促进了OLEDs的商业化进程。OLEDs的发光颜色调控可以通过发光材料的结构设计来实现。OLEDs可以包括一个发光层或者多个发光层以实现所需要的光谱。目前,绿色、黄色和红色磷光材料已经实现了商业化应用。商业化的OLED显示器,通常采用蓝色荧光和黄色,或绿色和红色磷光搭配来实现全彩显示。具有更饱和发光光谱、更高效率和更长使用寿命的发光材料是目前产业界迫切需要的。
金属配合物发光材料已经在产业上得到了应用,但其性能方面,如颜色饱和度、使用寿命等,仍不能满足要求。本发明提供了一系列金属配合物,研究发现,该类金属配合物可以发射深红至近红外光。进一步研究发现,该类配合物还具有聚集诱导发光增强的性质。
发明内容
针对现有技术存在的上述问题,本发明提供了一种金属配合物发光材料,该材料应用于有机电致发光器件体现了良好的光电性质和器件寿命。本发明还提供了一种电致发光器件,该器件包含了本发明的金属配合物。
有机电致发光材料,为具有式(I)结构的化合物:
其中:
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12和R13各自独立地选自:氢、氘、卤素、取代或未取代的具有1-20个碳原子的烷基、取代或未取代的具有3-20个碳原子的环烷基、取代或未取代的具有1-20个碳原子的烷氧基、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、或者氰基;
Ar1为至少包含两个N原子和3-30个碳原子的杂芳香基团;Ar2和Ar3各自独立地选自3-30个碳原子的芳香基团或者杂芳香基团,所述杂芳香基团中的杂原选自N、S、O原子;
所述取代为被氘、卤素或1-8个碳原子的烷基所取代。
通式(I)中,R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12和R13分别优选自:氢、氘、卤素、取代或未取代的具有1-6个碳原子的烷基、取代或未取代的具有3-6个碳原子的环烷基、取代或未取代的具有1-6个碳原子的烷氧基、取代或未取代的具有6-12个碳原子的芳基、取代或未取代的具有3-12个碳原子的杂芳基、或氰基;
Ar1为含2-4个杂原子和3-12个碳原子的杂芳香基团;Ar2和Ar3各自独立地选自3-12个碳原子的芳香基团或者杂芳香基团,所述杂芳香基团中的杂原选自N、S、O原子;
所述取代为被氘或1-4个碳原子的烷基所取代。
通式(I)中,R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12和R13分别进一步优选自:氢、氘、取代或未取代的具有1-4个碳原子的烷基、取代或未取代的具有3-6个碳原子的环烷基;Ar2和Ar3各自独立地选自5-10个碳原子芳香基团或者杂芳香基团。
通式(I)中,Ar1优选自如下芳香结构:
通式(I)中,Ar1进一步优选自如下芳香结构:
通式(I)中,优选的,Ar2和Ar3为相同芳香基团。
通式(I)中,优选的,Ar2和Ar3分别选自苯或者萘单元。
优选R1、R2、R3、R4、R5、R6、R7、R8、R9、R10为氢。
以下列出按照本发明的金属配合物例子,但不限于所列举的结构:
上述配合物的前体,即配体,结构式如下:
本发明的金属配合物发光材料,应用于电致发光器件能够获得深红至近红外的颜色,发射波长在620至1000nm之间,较好的在630至900nm之间,更好的在630至800nm之间。
本发明还提供一种上述金属配合物在有机光电子器件中的应用,所述光电子器件包括,但不限于,有机电致发光器件(OLEDs),有机薄膜晶体管(OTFTs),有机光伏器件(OPVs),发光电化学池(LCEs)和化学传感器,优选为OLEDs。
一种包含上述金属配合物的有机电致发光器件(OLEDs),该配合物作为发光器件中的发光材料。
本发明中的有机电致发光器件,包括阴极、阳极和有机层,所述有机层为空穴注入层、空穴传输层、发光层、空穴阻挡层、电子注入层、电子传输层中的一层或多层,这些有机层不必每层都存在。
所述空穴注入层、空穴传输层、空穴阻挡层、发光层和/或电子传输层中至少有一层含有式(I)所述的化合物。
优选地,结构式(I)所述的化合物所在层为发光层或电子传输层。
本发明的器件有机层的总厚度为1-1000nm,优选1-500nm,更优选5-300nm。
所述有机层可以通过蒸渡或溶液法形成薄膜。
本发明有益的技术效果主要在于:(1)本发明中的金属配合物应用于OLED器件中,具有良好的器件表现,发光效率得到了很大的改善,同时器件的使用寿命可以明显提升;(2)传统发光分子在聚集态时,由于分子间相互作用较强,导致发光量子产率降低,本发明中的金属配合物在聚集态时,具有聚集诱导发光增强的性质,有利于提高器件的发光效率。
附图说明
图1为本发明的有机电致发光器件结构图,
其中10代表为玻璃基板,20代表为阳极,30代表为空穴注入层,40代表为空穴传输层,50代表发光层,60代表空穴阻挡层,70代表电子传输层,80代表电子注入层,90代表阴极。
具体实施方式
本发明对材料的合成方法不作要求,为了更详细叙述本发明,特举以下例子,但是不限于此。
下式化合物原料均为市售。
实施例1
配合物4的合成
中间体4c的合成
将化合物4a(3.5g,19.2mmol)、化合4b(4.6g,23.0mmol)、醋酸钯(0.4g,0.2mmol)和CsF(3.0g,20.0mmol)溶于三氟甲磺酸(10mL)和水(30mL)的混合溶液中,加热至60℃,反应8小时。冷至室温后,将上述反应液加入水中,经二氯甲烷萃取三次,合并有机相。有机相经无水硫酸钠干燥后,旋除溶剂,剩余物经柱层析分离得白色固体(4.7g,产率71%)。ESI-MS(m/z):339.9(M+1)。备注:该反应在放大时,反应收率明显降低。
化合物4e的合成
氮气保护下,将化合物4c(17.0g,50.0mmol)溶于四氢呋喃(100mL),冷却至-78℃,逐滴加入正丁基锂BuLi(1.2eq),搅拌30分钟后,将化合物4d(17.3g,50.0mmol)的四氢呋喃溶液(30mL)滴加至上述溶液,搅拌30分钟后,升至室温,继续搅拌1小时。将上述反应液加入水中,经二氯甲烷萃取三次,合并有机相。有机相经无水硫酸钠干燥后,旋除溶剂得浅黄色固体。将上述固体溶于醋酸(50mL)中,加入浓硫酸(4mL),氮气保护下回流过夜。冷至室温后,将上述反应液加入水中,经二氯甲烷萃取三次,合并有机相。有机相经无水硫酸钠干燥后,旋除溶剂,剩余物经柱层析分离得浅黄色固体(18.6g,产率63%)。ESI-MS(m/z):588.1(M+1)。
化合物4f的合成
氮气保护下,将化合物4e(5.9g,10.0mmol)、邻羟基苯硼酸(1.6g,12.0mmol)、Pd(PPh3)4(0.6g,0.5mmol)、K2CO3(4.0g,30.0mmol)、四氢呋喃(50mL)和水(5mL)依次加入Schlenk管中。加热至80℃,反应24小时。冷至室温后,将上述反应液加入水中,经二氯甲烷萃取三次,合并有机相。有机相经无水硫酸钠干燥后,旋除溶剂,剩余物经柱层析分离得灰白色固体(4.9g,产率81%)。ESI-MS(m/z):600.2(M-1)。
化合物4g的合成
氮气保护下,将化合物4f(4.9g,8.1mmol),联硼酸频哪醇酯(37mmol,10.0mmol),醋酸钾(2.5g,25.0mmol),Pd(dppf)Cl2(0.3g,0.4mmol)溶入二氧六环(50mL)中,氮气置换数次后加热回流反应过夜。冷至室温后,将上述反应液加入水中,经乙酸乙酯萃取三次,合并有机相。有机相经无水硫酸钠干燥后,旋除溶剂,剩余物经柱层析分离得灰白色固体(4.5g,产率85%)。ESI-MS(m/z):648.4(M-1)。
化合物4h的合成
氮气保护下,将化合物4g(4.2g,6.5mmol)、氯代均三嗪(1.0g,8.5mmol)、Pd(PPh3)4(0.3g,0.3mmol)、K2CO3(1.3g,10.0mmol)、四氢呋喃(30mL)和水(5mL)依次加入Schlenk管中。加热至80℃,反应24小时。冷至室温后,将上述反应液加入水中,经二氯甲烷萃取三次,合并有机相。有机相经无水硫酸钠干燥后,旋除溶剂,剩余物经柱层析分离得浅黄色固体(2.4g,产率62%)。ESI-MS(m/z):601.3(M-1)。
配合物4的合成
将化合物4h(2.0g,3.3mmol)、氯铂酸钾(1.7g,4.0mmol)和250mL乙酸加入烧瓶中,氮气保护下,回流搅拌48小时。冷至室温后,将上述反应液加入水中,过滤得粗产物,重结晶得红色固体(2.4g,产率90%)。ESI-MS(m/z):796.3(M+1)。
实施例2
配合物29的合成
化合物29b的合成
用中间体29a替换中间体氯代均三嗪,参考化合物4h的合成方法制备化合物29b,得浅黄色固体(3.2g,产率70%)。ESI-MS(m/z):650.3(M-1)。
配合物29的合成
用中间体29b替换中间体4h,参考配合物4的合成方法制备化合物配合物29,得红色固体(2.9g,产率85%)。ESI-MS(m/z):845.3(M+1)。
实施例3
配合物32的合成
化合物32b的合成
用中间体32a替换中间体氯代均三嗪,参考化合物4h的合成方法制备化合物32b,得浅黄色固体(2.1g,产率55%)。ESI-MS(m/z):639.3(M-1)。
配合物32的合成
用中间体32b替换中间体4h,参考配合物4的合成方法制备化合物配合物32,得红色固体(2.3g,产率81%)。ESI-MS(m/z):834.3(M+1)。
实施例4
配合物36的合成
化合物36b的合成
用中间体32a替换中间体氯代均三嗪,参考化合物4h的合成方法制备化合物32b,得浅黄色固体(2.1g,产率55%)。ESI-MS(m/z):700.3(M-1)。
配合物36的合成
用中间体36b替换中间体4h,参考配合物4的合成方法制备化合物配合物36,得深红色固体(1.9g,产率65%)。ESI-MS(m/z):895.5(M+1)。
实施例5
配合物54的合成
用中间体54a替换中间体氯代均三嗪,参考化合物4h的合成方法制备化合物54b,得浅黄色固体(3.5g,产率69%)。ESI-MS(m/z):664.4(M-1)。
配合物54的合成
用中间体54b替换中间体4h,参考配合物4的合成方法制备化合物配合物54,得红色固体(1.3g,产率81%)。ESI-MS(m/z):859.2(M+1)。
实施例6-10
使用本发明的配合物发光材料制备电致发光器件,器件结构见图1。
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30秒。
然后,在ITO上蒸镀10nm厚的HATCN作为空穴注入层30。
然后,蒸镀化合物NPB,形成40nm厚的空穴传输层40。
然后,在空穴传输层上蒸镀20nm厚的发光层50,发光层由实施例1-5中的配合物4(实施例6)、29(实施例7)、32(实施例8)、36(实施例9)或54(实施例10)(5%)分别与CBP(95%)混合掺杂组成。
然后,在发光层上蒸镀10nm厚的BAlq作为空穴阻挡层60
然后,在空穴阻挡层上蒸镀40nm厚的Alq3作为电子传输层70。
最后,蒸镀1nm LiF为电子注入层80和100nm Al作为器件阴极90。
对比例
使用(pq)2Ir(acac)替换上述本发明中的化合物,依照相同方法制备有机发光器件。
器件中HATCN、NPB、CBP、(pq)2Ir(acac)、Alq3及BAlq结构式如下:
实施例6-10及比较例中有机电致发光器件在10mA/cm2电流密度下的器件性能列于表1:
表1
由表1数据可以看出,相同条件下,应用本发明中的化合物制备的有机电致发光器件的效率均优于比较例,相比于常见的红光材料(pq)2Ir(acac),本发明的金属配合物材料应用于有机电致发光器件,具有更低的驱动电压,器件寿命也有很大程度改善,且发射深红或近红外光,更符合显示产业对于发光材料的要求,具有良好的产业化前景。
实施例11
金属配合物4、29、32、36和54在PMMA薄膜中和二氯甲烷溶液中的发光量子产率比值(ФPMMA/Ф溶液)列于表2:
表2
通过表2的数据可以发现,本发明的金属配合物在聚集态的量子产率高于在溶液中的量子产率。铂配合物材料在聚集态下,由于浓度淬灭效应,发光量子产率通常较低。本发明的金属配合物体现出了聚集诱导发光增强的性质,可见,本发明取得了预料不到的效果。
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,均应在权利要求书所限制的保护范围内。
Claims (14)
1.一种金属配合物,为具有式(I)结构的化合物:
其中:
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12和R13各自独立地选自:氢、氘、卤素、取代或未取代的具有1-20个碳原子的烷基、取代或未取代的具有3-20个碳原子的环烷基、取代或未取代的具有1-20个碳原子的烷氧基、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个碳原子的杂芳基或者氰基;
Ar1为至少包含两个N原子和3-30个碳原子的杂芳香基团;Ar2和Ar3各自独立地选自3-30个碳原子的芳香基团或者杂芳香基团,所述杂芳香基团中的杂原选自N、S、O原子;
所述取代为被氘、卤素或1-8个碳原子的烷基所取代。
2.根据权利要求1所述的金属配合物,所述式(I)中,R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12和R13分别选自:氢、氘、卤素、取代或未取代的具有1-6个碳原子的烷基、取代或未取代的具有3-6个碳原子的环烷基、取代或未取代的具有1-6个碳原子的烷氧基、取代或未取代的具有6-12个碳原子的芳基、取代或未取代的具有3-12个碳原子的杂芳基或氰基;
Ar1为含2-4个杂原子和3-12个碳原子的杂芳香基团;Ar2和Ar3各自独立地选自3-12个碳原子的芳香基团或者杂芳香基团,所述杂芳香基团中的杂原选自N、S、O原子;
所述取代为被氘或1-4个碳原子的烷基所取代。
3.根据权利要求2所述的金属配合物,所述式(I)中,R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12和R13分别选自:氢、氘、取代或未取代的具有1-4个碳原子的烷基、取代或未取代的具有3-6个碳原子的环烷基;Ar2和Ar3各自独立地选自5-10个碳原子芳香基团或者杂芳香基团。
6.根据权利要求1-5任一所述的金属配合物,其中Ar2和Ar3为相同芳香基团。
7.根据权利要求6所述的金属配合物,其中Ar2和Ar3选自苯或者萘单元基团。
8.根据权利要求7所述的金属配合物,其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10为氢,Ar2和Ar3为苯。
11.权利要求1-9任一所述的金属配合物在有机光电子器件中的应用,所述有机光电子器件包含有机电致发光器件,有机薄膜晶体管,有机光伏器件,发光电化学池和化学传感器。
12.一种有机电致发光器件,包括阴极、阳极和有机层,所述有机层为空穴注入层、空穴传输层、发光层、空穴阻挡层、电子注入层、电子传输层中的一层或多层,所述有机层中含有权利要求1-9任一所述的金属配合物。
13.根据权利要求12所述的有机电致发光器件,权利要求1-9任一所述的金属配合物位于发光层或电子传输层。
14.根据权利要求12所述的有机电致发光器件,所述有机层的总厚度为1-1000nm,所述有机层通过蒸渡或溶液法形成薄膜。
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WO2022037613A1 (en) * | 2020-08-19 | 2022-02-24 | The University Of Hong Kong | Spiro-cyclometalated iridium emitters for oled applications |
WO2023116587A1 (zh) * | 2021-12-22 | 2023-06-29 | 广东阿格蕾雅光电材料有限公司 | 双核铂配合物发光材料及其应用 |
WO2023207622A1 (zh) * | 2022-04-25 | 2023-11-02 | 广东阿格蕾雅光电材料有限公司 | 基于四芳基乙烯骨架结构的四齿型铂配合物发光材料及其应用 |
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