CN116528649A - 一种基于噻吨酮衍生物的有机电致发光材料的oled器件 - Google Patents
一种基于噻吨酮衍生物的有机电致发光材料的oled器件 Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 claims abstract description 7
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- 238000006243 chemical reaction Methods 0.000 description 25
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- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
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- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
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- 229910000510 noble metal Inorganic materials 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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Abstract
本发明公开了一种基于噻吨酮衍生物的有机电致发光材料的OLED器件,涉及OLED技术领域。本发明所述OLED器件结构如下:ITO/HATCN/TAPC/TcTa/mCP/有机电致发光材料/TmPyPB/LiF/Al。其中有机电致发光材料是以咔唑并环噻吨酮为核心的化合物1‑3中一种。本发明的OLED器件效率高,效率滚降程度较小,同时还具有低的启动电压,在高亮度下能保持较高器件效率。
Description
技术领域
本发明属于OLED技术领域,具体涉及一种基于噻吨酮衍生物的有机电致发光材料的OLED器件。
背景技术
有机电致发光器件又称有机发光二极管(OLEDs),是一类基于有机发光材料,其是将电能转换为光能的器件,其工作原理是在电场驱动下,载流子从两极注入并在发光层复合导致发光。然而,传统荧光材料制备的OLEDs器件效率很低,因为其激子利用率仅能达到25%。剩余的75%的三线态激子会以非辐射衰减形式回到基态而不发光。
基于磷光材料的OLEDs能够实现100%的激子利用率,但其含有贵金属、稳定性差、制备成本高等缺点限制了其在电致发光器件中的实际应用。(Nat.Photon.,2012,6:253-258;Phys.Rev.B,1999,60:14422-14428;Chem.Mater.2012,24,2178–2185;Adv.Mater.2013,25,2666–2671;Adv.Funct.Mater.2013,23,2329–2337;Adv.Funct.Mater.2014,24,3621–3630)。2012年,Chihaya Adachi教授等人在《自然》杂志上首次报道了纯有机TADF(Thermally Activated Delayed Fluorescence)材料以及其OLEDs器件。TADF材料采用小的ΔEST进行分子设计,使得三线态激子可通过RISC(ReverseInter-System Crossing)过程回到单线态并发光,因此,理论上激子利用率可实现100%。TADF可以实现100%激子利用率的特性、独特的发光机制。此外,其还具有较低的成本和较好的稳定性以及人们对可持续发展和环境保护的日益增加需求。TADF材料是目前最有潜力的OLEDs发光材料之一。但由于RISC是一个上转化过程,容易造成大量三线态激子堆积,其亮度难以进一步提高,且效率滚降问题依然严重。
因此,开发一类高稳定性、高发光亮度和高发光效率的OLED器件是目前行业需要亟待解决的技术问题。
发明内容
针对现有技术的不足,本发明提供了一种基于噻吨酮衍生物的有机电致发光材料的OLED器件。
为了实现上述发明目的,本发明提供以下技术方案:
一种基于噻吨酮衍生物的有机电致发光材料的OLED器件,所述OLED器件结构如下:
ITO/HATCN/TAPC/TcTa/mCP/有机电致发光材料/TmPyPB/LiF/Al
所述有机电致发光材料为以下化合物中的一种:
优选的,所述有机电致发光材料中化合物1的合成路线如下:
进一步优选的,所述有机电致发光材料中化合物1的合成方法如下:
将C13H6Br2OS(即M化合物,结构式如下所示)和5-苯基-5,11-二氢吲哚并[3,2-B]咔唑、叔丁醇钠、三(二亚苄基丙酮)二钯和四氟硼酸三叔丁基膦加入至反应瓶中,抽换气三次,然后加入甲苯,进行加热反应,反应结束后将反应液采用二氯甲烷和水按体积比为1:1混合液进行萃取,收集二氯甲烷相为萃取液浓缩后进行过柱,得到化合物1。
其中化合物M的结构式如下所示:
优选的,所述有机电致发光材料中化合物2的合成路线如下:
进一步优选的,所述有机电致发光材料中化合物2的合成方法如下:
将M化合物、5-苯基-5,12-二氢吲哚并[3,2-A]咔唑、叔丁醇钠、三(二亚苄基丙酮)二钯和四氟硼酸三叔丁基膦加入至反应瓶中,抽换气三次,加入甲苯后进行加热反应,反应结束后将反应液采用二氯甲烷和水按体积比为1:1制成的混合液进行萃取,收集二氯甲烷相为萃取液,将萃取液浓缩后进行过柱纯化,得到化合物2。
优选的,所述有机电致发光材料中化合物3的合成路线如下:
进一步优选的,所述有机电致发光材料中化合物3的合成方法如下:
将M、12-苯基-5,12-二氢吲哚[3,2-A]咔唑、叔丁醇钠、三(二亚苄基丙酮)二钯和四氟硼酸三叔丁基膦加入至反应瓶中,抽换气三次,加入甲苯后进行加热反应,反应结束后将反应液采用二氯甲烷和水混合液进行萃取,收集二氯甲烷相为萃取液,将萃取液浓缩后进行过柱纯化,得到化合物3。
本发明所述化合物M的合成方法如下:
(1)将3-溴硫酚(20mmol)、4-溴-2-氟苯甲腈(30mmol)和碳酸钾(40mmol),加入至反应瓶中,抽换气三次,加入100mL无水N,N-二甲基甲酰胺,加热反应,反应温度150℃。反应结束后将反应液采用二氯甲烷和水混合液进行萃取,收集二氯甲烷相为萃取液,浓缩后做粉过柱,得到中间体1,产率94%;
(2)将中间体1溶于54mL乙醇中,加入反应瓶中,然后往反应瓶中加入54mL氢氧化钾(388mmol)水溶液,室温搅拌反应,反应后加入80mL盐酸。获得的固体经过水洗,得到中间体2,产率83%。
(3)将中间体2溶于140mL二氯甲烷中,加入反应瓶中,然后在冰浴条件下往反应瓶中逐滴加入三氟乙酸酐(42mmol),搅拌5分钟后再逐滴加入三氟化硼乙醚(36mmol)搅拌反应至室温8小时。反应物用饱和碳酸氢钠水溶液中和,反应结束后将反应液采用二氯甲烷和水按体积比为1:1制成的混合液进行萃取,收集二氯甲烷相为萃取液,浓缩后做粉过柱,得到化合物M。
与现有技术相比,本发明具有以下有益效果:
本发明的OLED器件结构如下:ITO/HATCN/TAPC/TcTa/mCP/有机电致发光材料/TmPyPB/LiF/Al。本发明的OLED器件效率高,效率滚降程度较小,同时还具有低的启动电压,在高亮度下效率滚降程度更小。
附图说明
图1为实施例1制备的OLED器件的J–V–L曲线图;
图2为实施例1制备的OLED器件的外量子效率随亮度变化的曲线图;
图3为实施例2制备的OLED器件的J–V–L曲线图;
图4为实施例2制备的OLED器件的外量子效率随亮度变化的曲线图;
图5为实施例3制备的OLED器件的J–V–L曲线图;
图6为实施例3制备的OLED器件的外量子效率随亮度变化的曲线图。
具体实施方式
为使本发明的目的、特征和优点能够更加明显易懂,下面对本发明的具体实施方式做详细的说明。但是,本发明可以以许多不同的形式来实现,并不限于本文所描述的实施例。相反地,提供这些实施例的目的是使对本发明的公开内容更加透彻全面。
实施例1
一种基于噻吨酮衍生物的有机电致发光材料的OLED器件,所述OLED器件结构如下:
ITO/HATCN/TAPC/TcTa/mCP/有机电致发光材料/TmPyPB/LiF/Al
其中有机电致发光材料为化合物1,其结构式如下:
其合成路线如下:
具体合成步骤是将化合物M(1mmol)、5-苯基-5,11-二氢吲哚并[3,2-B]咔唑(2.5mmol)、叔丁醇钠(6mmol)、三(二亚苄基丙酮)二钯(0.16mmol)和四氟硼酸三叔丁基膦(0.16mmol)加入至反应瓶中,抽换气三次,加入50mL甲苯,加热反应,反应温度110℃。将反应液采用二氯甲烷和水按体积比为1:1制成的混合液进行萃取,收集二氯甲烷相为萃取液,浓缩后过柱纯化,得到化合物1,产率55%。
对该化合物1进行检测,结构如下:
1H NMR(400MHz,THF-d8)δ8.95(d,J=8.6Hz,2H),8.39(s,2H),8.26–8.15(m,8H),8.04–8.01(m,2H),7.80–7.67(m,8H),7.64(d,J=8.2Hz,2H),7.56–7.51(m,2H),7.48–7.35(m,6H),7.31–7.19(m,4H).13C NMR(100MHz,CDCl3)δ178.27,142.53,141.16,139.02,138.16,137.63,136.02,132.18,130.10,127.50,126.47,124.94,124.02,123.31,122.78,120.61,100.25,100.10。
高分辨质谱HRMS(ESI,m/z)calcd.for C61H37N4O1S1[M+H]+:895.2502;found:895.2514。
图1为化合物1作为有机电致发光材料制成的OLED器件的J–V–L曲线图,从图中可以看出该OLED器件最大亮度高并且启动电压低,为50440cd/m2,3.4V。图2为该OLED器件的外量子效率随亮度变化的曲线图,从图中可以看出,基于化合物1的器件其最大外量子效率为21.1%,当亮度为10000cd/m2时,外量子效率维持在7.5%。
实施例2
一种基于噻吨酮衍生物的有机电致发光材料的OLED器件,所述OLED器件结构如下:
ITO/HATCN/TAPC/TcTa/mCP/有机电致发光材料/TmPyPB/LiF/Al
其中有机电致发光材料为化合物2,其结构式如下:
合成路线如下:
将化合物M(1mmol)、5-苯基-5,12-二氢吲哚并[3,2-A]咔唑(2.5mmol)、叔丁醇钠(6mmol)、三(二亚苄基丙酮)二钯(0.16mmol)和四氟硼酸三叔丁基膦(0.16mmol)加入至反应瓶中,抽换气三次,加入50mL甲苯,加热反应,反应温度110℃。将反应液采用二氯甲烷和水按体积比为1:1制成的混合液进行萃取,收集二氯甲烷相为萃取液,浓缩后进行过柱纯化,得到最终产物化合物2,产率77%。
对化合物2进行检测,其结果如下:
1H NMR(400MHz,CD2Cl2)δ8.97(d,J=8.4Hz,2H),8.28–8.07(m,4H),7.94–7.87(m,2H),7.79–7.52(m,12H),7.45–7.19(m,10H),6.86–6.78(m,2H),6.26(d,J=8.1Hz,2H).13CNMR(100MHz,CDCl3)δ179.84,143.16,142.62,142.02,140.16,138.84,137.21,132.96,131.33,129.38,127.70,126.57,124.58,122.74,122.53,119.10,113.16,104.20.
高分辨质谱HRMS(ESI,m/z)calcd.for C61H37N4O1S1[M+H]+:895.2502;found:895.2505。
图3为化合物2作为有机电致发光材料料的OLED器件的J–V–L曲线图,从图中可以看出,该OLED器件的最大亮度高并且启动电压低,为56570cd/m2,3.2V。图4为该OLED器件的外量子效率随亮度变化的曲线图,从图中可以看出,该OLED器件其最大外量子效率为20.5%,当亮度为10000cd/m2时,外量子效率维持在12.1%。
实施例3
一种基于噻吨酮衍生物的有机电致发光材料的OLED器件,所述OLED器件结构如下:
ITO/HATCN/TAPC/TcTa/mCP/有机电致发光材料/TmPyPB/LiF/Al
其中有机电致发光材料为化合物3,其结构式如下:
该化合物3的合成路线如下:
将化合物M(1mmol)、12-苯基-5,12-二氢吲哚[3,2-A]咔唑(2.5mmol)、叔丁醇钠(6mmol)、三(二亚苄基丙酮)二钯(0.16mmol)和四氟硼酸三叔丁基膦(0.16mmol)加入至反应瓶中,抽换气三次,加入50mL甲苯,加热反应,反应温度110℃。将反应液采用二氯甲烷和水按体积比为1:1制成的混合液进行萃取,收集二氯甲烷相为萃取液,浓缩后进行过柱纯化,得到最终产物化合物3,产率72%。
对化合物3进行检测,其结果如下:
1H NMR(400MHz,CD2Cl2)δ8.92(d,J=8.6Hz,2H),8.25(d,J=8.5Hz,2H),8.17(d,J=7.1Hz,2H),7.95(d,J=1.9Hz,2H),7.85–7.82(m,2H),7.71–7.64(m,10H),7.52–7.46(m,4H),7.38–7.26(m,8H),6.85–6.81(m,2H),5.98(d,J=8.2Hz,2H)。
13C NMR(100MHz,CD2Cl2)δ178.84,140.89,133.17,131.31,130.21,126.69,123.38,121.84,121.53,120.31,119.43,118.35,110.44,109.82,104.74,101.15。
高分辨质谱HRMS(ESI,m/z)calcd.for C61H37N4O1S1[M+H]+:895.2502;found:895.2528。
图5为实施例3作为有机电致发光材料的OLED器件的J–V–L曲线图,从图中可以看出,该OLED器件的最大亮度高并且启动电压低,为43960cd/m2,3.4V。图6为该OLED器件的外量子效率随亮度变化的曲线图,从图中可以看出,该OLED器件的最大外量子效率为23.0%,当亮度为10000cd/m2时,外量子效率维持在10.5%。
从实施例1-3中可以看出,采用本发明以咔唑并环噻吨酮为核心的有机光电材料作为发光层制备出的OLED器件效率高,效率滚降程度较小;基于这类材料制备出的结构简单的OLED器件,具有低的启动电压,较高的效率,且在高亮度下效率滚降程度更小。这类高亮度、低滚降材料在有机电致发光领域有很广阔的商业前景。
以上所述实施例仅表达了本发明的几种实施方式,其描述较为具体和详细,但并不能因此而理解为对本发明专利范围的限制。应当指出的是,对于本领域的普通技术人员来说,在不脱离本发明构思的前提下,还可以做出若干变形和改进,这些都属于本发明的保护范围。因此,本发明专利的保护范围应以所附权利要求为准。
Claims (4)
1.一种基于噻吨酮衍生物的有机电致发光材料的OLED器件,其特征在于,所述OLED器件结构如下:
ITO/HATCN/TAPC/TcTa/mCP/有机电致发光材料/TmPyPB/LiF/Al
所述有机电致发光材料为以下化合物中的一种:
2.根据权利要求1所述基于噻吨酮衍生物的有机电致发光材料的OLED器件,所述有机电致发光材料中化合物1的合成路线如下:
3.根据权利要求1所述基于噻吨酮衍生物的有机电致发光材料的OLED器件,所述有机电致发光材料中化合物2的合成路线如下:
4.根据权利要求1所述基于噻吨酮衍生物的有机电致发光材料的OLED器件,所述有机电致发光材料中化合物3的合成路线如下:
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