CN112574109A - 一种有机电致发光化合物及其应用 - Google Patents

一种有机电致发光化合物及其应用 Download PDF

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CN112574109A
CN112574109A CN202011559409.9A CN202011559409A CN112574109A CN 112574109 A CN112574109 A CN 112574109A CN 202011559409 A CN202011559409 A CN 202011559409A CN 112574109 A CN112574109 A CN 112574109A
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崔彩
丁兴立
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Suzhou Bofanxi Technology Co Ltd
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Abstract

本发明公开了一种有机电致发光化合物及其应用，所述有机电致发光化合物具有如式Ⅰ所示结构：
Figure DDA0002859875020000011
，其中，Ar1、Ar2各自独立的代表具有C6～C60的芳香族或C6～C60的杂芳香族环系。一种OLED器件用空穴传输层，所述空穴传输层包括上述的有机电致发光化合物。一种OLED器件，所述OLED器件包括阳极、阴极以及位于所述阳极和所述阴极之间的至少一层有机薄膜层；所述有机薄膜层包括空穴传输层，还包括空穴注入层、电子阻挡层、空穴阻挡层、发光层、电子传输层和电子注入层中的任意一种或至少两种的组合；所述空穴传输层为上述的OLED器件用空穴传输层。本发明有机电致发光化合物具有良好空穴传输性能以及稳定性，可用于制造工作寿命较高的OLED器件。

Description

一种有机电致发光化合物及其应用
技术领域
本发明属于有机电致发光材料技术领域，尤其涉及一种有机电致发光化合物及其应用。
背景技术
电致发光装置(EL装置)为自发光装置，其优点在于具有较宽的视角、较大的对比率和较快的响应时间。目前，第一个有机EL装置由伊士曼柯达(Eastman Kodak)通过使用芳香族二胺小分子和金属铝络合物作为用于形成发光层的材料[《应用物理学报(Appl.Phys.Lett.)》51,913,1987]。
现有技术中，通常在空穴传输层或空穴注入层中使用空穴传输材料，常用的空穴传输材料为三芳胺衍生物，其含有至少两个三芳基胺基团或至少一个三芳基胺基团和至少一个咔唑基团；上述化合物通常来源于二芳基氨基取代基的三苯胺(TPA型)、二芳基氨基取代的联苯衍生物(TAD型)或这些基础化合物的组合。将上述化合物用于荧光OLED，或磷光OLED，特别是在用于有机电致发光器件时，工作电压、效率、寿命以及升华期间的热稳定性方面，均需要改进。
发明内容
本发明目的在于提供一种有机电致发光化合物及其应用，该有机电致发光化合物具有良好空穴传输性能以及稳定性，可用于制造工作寿命较高的OLED器件。
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如式Ⅰ所示结构：
Figure BDA0002859875010000011
其中，Ar1、Ar2各自独立的代表具有C6～C60的芳香族或C6～C60的杂芳香族环系。
上述技术方案中进一步改进的技术方案如下：
上述方案中，所述其中Ar1、Ar2各自独立的代表苯、萘、菲、芴、二苯并呋喃或二苯并噻吩咔唑或者它们的组合。
本发明的目的之二在于提供一种OLED器件用空穴传输层，所述空穴传输层包括如目的之一所述的有机电致发光化合物。
本发明的目的之三在于提供一种OLED器件，所述OLED器件包括阳极、阴极以及位于所述阳极和所述阴极之间的至少一层有机薄膜层；所述有机薄膜层包括空穴传输层，还包括空穴注入层、电子阻挡层、空穴阻挡层、发光层、电子传输层和电子注入层中的任意一种或至少两种的组合；
所述空穴传输层为如目的之二所述的OLED器件用空穴传输层。
本发明的目的之四在于提供一种电子设备，所述电子设备包括如目的之二所述的OLED器件。
由于上述技术方案的运用，本发明与现有技术相比具有下列优点：
1、本发明提供的有机电致发光化合物具有7元环结构，通过分子结构和取代基的设计赋予了所述有机电致发光化合物较高的玻璃化转变温度和良好的热稳定性，避免其在高温沉积工艺中的降解；并且显著提升了其作为空穴传输层的空穴传输性能以及稳定性，使包含其的OLED器件具有高发光效率和长工作寿命，改善了功率效率和功率消耗。
2、本发明所述的有机电致发光化合物适用于荧光OLED器件和磷光OLED器件，尤其适用于磷光OLED器件。
具体实施方式
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如式Ⅰ所示结构：
Figure BDA0002859875010000021
其中，其中，Ar1、Ar2各自独立的代表具有C6～C60的芳香族或C6～C60的杂芳香族环系。
所述有机电致发光化合物通过分子结构和取代基的设计赋予了所述有机电致发光化合物较高的玻璃化转变温度和良好的热稳定性，避免其在高温沉积工艺中的降解；并且显著提升了其作为空穴传输层的空穴传输性能以及稳定性，使包含其的OLED器件具有高发光效率和长工作寿命，改善了功率效率和功率消耗。
所述有机电致发光化合物选自式H1～式H30中的一种或多种：
Figure BDA0002859875010000031
Figure BDA0002859875010000041
Figure BDA0002859875010000053
本发明的目的之二在于提供一种OLED器件用空穴传输层，所述空穴传输层包括如目的之一所述的有机电致发光化合物。
本发明的目的之三在于提供一种OLED器件，所述OLED器件包括阳极、阴极以及位于所述阳极和所述阴极之间的至少一层有机薄膜层；所述有机薄膜层包括空穴传输层，还包括空穴注入层、电子阻挡层、空穴阻挡层、发光层、电子传输层和电子注入层中的任意一种或至少两种的组合；
所述空穴传输层为如目的之二所述的OLED器件用空穴传输层。
本发明的目的之四在于提供一种电子设备，所述电子设备包括如目的之二所述的OLED器件。
下面结合实施例对本发明作进一步描述：
以下实施例所涉及的化合物结构如下：
Figure BDA0002859875010000051
合成实施例：
实施例1：本实施例提供一种有机电致发光化合物H1，结构如下：
Figure BDA0002859875010000052
所述H1的制备方法包括如下步骤：
(1)合成H1：
Figure BDA0002859875010000061
向250ml三口瓶中，加入M-1(5g、0.014mol)和3-(4-溴苯基)-9-苯基咔唑(5.5g、0.014mol)，加入甲苯100ml，搅拌下加入叔丁醇钠(1.7g、0.018mol)、Pd2(dba)3(0.064g、0.00007mol)，置换氮气，加入三叔丁基膦10％甲苯溶液0.28g，开始加热，缓缓升温至80℃(反应过程保持氮气保护)，反应2小时，HPLC检测(M-1<1％)、停止反应，降温至室温。反应结束后，冷却至25℃，食盐水洗2次，有机相加入无水硫酸钠干燥；柱层析，用甲苯作为洗脱剂；浓缩，得到粗品，用甲苯重结晶，得到产品7.6g产品H1，纯度>99％，收率80％。
对H1化合物进行了质谱检测，测得m/z：676。
对H1化合物进行了核磁检测，数据解析如下：
1HNMR(300MHz，CDCl3)δ8.55(d，1H)，δ7.99(d，1H)，δ7.94～7.89(m，3H)，δ7.78～7.75(m，4H)，δ7.65～7.60(m，4H)，δ7.58～7.50(m，6H)，δ7.49～7.41(m，4H)，δ7.37～7.35(m，3H)δ7.24～7.16(m，4H)，δ1.63(s，6H)。
实施例2：本实施例提供一种有机电致发光化合物H2，结构如下：
Figure BDA0002859875010000062
所述H2的制备方法包括如下步骤：
(1)合成H2：
Figure BDA0002859875010000071
向250ml三口瓶中，加入M-2(5g、0.014mol)和3-(4-溴苯基)-9-苯基咔唑(5.5g、0.014mol)，加入甲苯100ml，搅拌下加入叔丁醇钠(1.7g、0.018mol)、Pd2(dba)3(0.064g、0.00007mol)，置换氮气，加入三叔丁基膦10％甲苯溶液0.28g，开始加热，缓缓升温至80℃(反应过程保持氮气保护)，反应2小时，HPLC检测(M-2<1％)、停止反应，降温至室温。反应结束后，冷却至25℃，食盐水洗2次，有机相加入无水硫酸钠干燥；柱层析，用甲苯作为洗脱剂；浓缩，得到粗品，用甲苯重结晶，得到产品7.6g产品H2，纯度>99％，收率80％。
对H2化合物进行了质谱检测，测得m/z：676。
对H2化合物进行了核磁检测，数据解析如下：
1HNMR(300MHz，CDCl3)δ8.55(d，1H)，δ7.99(d，1H)，δ7.94～7.89(m，3H)，δ7.78～7.75(m，4H)，δ7.65～7.35(m，16H)δ7.24～7.16(m，4H)，δ6.91(d,1H)δ1.63(s，6H)。
实施例3：本实施例提供一种有机电致发光化合物H4，结构如下：
Figure BDA0002859875010000072
所述H4的制备方法包括如下步骤：
(1)合成H4：
Figure BDA0002859875010000081
向250ml三口瓶中，加入M-3(5.2g、0.014mol)和3-(4-溴苯基)-9-苯基咔唑(5.5g、0.014mol)，加入甲苯100ml，搅拌下加入叔丁醇钠(1.7g、0.018mol)、Pd2(dba)3(0.064g、0.00007mol)，置换氮气，加入三叔丁基膦10％甲苯溶液0.28g，开始加热，缓缓升温至80℃(反应过程保持氮气保护)，反应2小时，HPLC检测(M-3<1％)、停止反应，降温至室温。反应结束后，冷却至25℃，食盐水洗2次，有机相加入无水硫酸钠干燥；柱层析，用甲苯作为洗脱剂；浓缩，得到粗品，用甲苯重结晶，得到产品7.7g产品H4，纯度>99％，收率80％。
对H4化合物进行了质谱检测，测得m/z：690。
对H4化合物进行了核磁检测，数据解析如下：
1HNMR(300MHz，CDCl3)δ8.55(d，1H)，δ8.22(s，1H)，δ7.99～7.89(m，4H)，δ7.79～7.77(m，3H)，δ7.65～7.35(m，14H)δ7.31～7.16(m，5H),δ1.63(s，6H)。
实施例4：本实施例提供一种有机电致发光化合物H11，结构如下：
Figure BDA0002859875010000082
所述H11的制备方法包括如下步骤：
(1)合成H11：
Figure BDA0002859875010000091
向250ml三口瓶中，加入M-2(5g、0.014mol)和2-溴-9,9'-螺二芴(5.5g、0.014mol)，加入甲苯100ml，搅拌下加入叔丁醇钠(1.7g、0.018mol)、Pd2(dba)3(0.064g、0.00007mol)，置换氮气，加入三叔丁基膦10％甲苯溶液0.28g，开始加热，缓缓升温至80℃(反应过程保持氮气保护)，反应2小时，HPLC检测(M-2<1％)、停止反应，降温至室温。反应结束后，冷却至25℃，食盐水洗2次，有机相加入无水硫酸钠干燥；柱层析，用甲苯作为洗脱剂；浓缩，得到粗品，用甲苯重结晶，得到产品7.6g产品H11，纯度>99％，收率80％。
对H11化合物进行了质谱检测，测得m/z：673。
对H11化合物进行了核磁检测，数据解析如下：
1HNMR(300MHz，CDCl3)δ7.90～7.86(m，5H)，δ7.78～7.75(m，3H)，δ7.65(d，1H)，δ7.55～7.16(m，19H)，δ7.91(d，1H)，δ1.63(s，6H)。
实施例5：本实施例提供一种有机电致发光化合物H17，结构如下：
Figure BDA0002859875010000092
所述H17的制备方法包括如下步骤：
(1)合成H17：
Figure BDA0002859875010000101
向250ml三口瓶中，加入M-1(5g、0.014mol)和4-溴-9,9'-螺二芴(5.5g、0.014mol)，加入甲苯100ml，搅拌下加入叔丁醇钠(1.7g、0.018mol)、Pd2(dba)3(0.064g、0.00007mol)，置换氮气，加入三叔丁基膦10％甲苯溶液0.28g，开始加热，缓缓升温至80℃(反应过程保持氮气保护)，反应2小时，HPLC检测(M-2<1％)、停止反应，降温至室温。反应结束后，冷却至25℃，食盐水洗2次，有机相加入无水硫酸钠干燥；柱层析，用甲苯作为洗脱剂；浓缩，得到粗品，用甲苯重结晶，得到产品7.6g产品H17，纯度>99％，收率80％。
对H17化合物进行了质谱检测，测得m/z：673。
对H17化合物进行了核磁检测，数据解析如下：
1HNMR(300MHz，CDCl3)δ7.90～7.86(m，5H)，δ7.78～7.75(m，3H)，δ7.65(d，2H)，δ7.58～7.16(m，19H)，δ1.63(s，6H)。
实施例6：本实施例提供一种有机电致发光化合物H26，结构如下：
Figure BDA0002859875010000102
所述H26的制备方法包括如下步骤：
(1)合成H26：
Figure BDA0002859875010000111
向250ml三口瓶中，加入M-1(5g、0.014mol)和4-溴-9,9-二苯基芴(5.6g、0.014mol)，加入甲苯100ml，搅拌下加入叔丁醇钠(1.7g、0.018mol)、Pd2(dba)3(0.064g、0.00007mol)，置换氮气，加入三叔丁基膦10％甲苯溶液0.28g，开始加热，缓缓升温至80℃(反应过程保持氮气保护)，反应2小时，HPLC检测(M-2<1％)、停止反应，降温至室温。反应结束后，冷却至25℃，食盐水洗2次，有机相加入无水硫酸钠干燥；柱层析，用甲苯作为洗脱剂；浓缩，得到粗品，用甲苯重结晶，得到产品7.6g产品H26，纯度>99％，收率80％。
对H26化合物进行了质谱检测，测得m/z：675。
对H26化合物进行了核磁检测，数据解析如下：
1HNMR(300MHz，CDCl3)δ7.90(m，2H)，δ7.78～7.75(m，3H)，δ7.65(d，2H)，δ7.56～7.38(m，7H)，δ7.28～7.10(m，17H)，δ1.63(s，6H)。
以下为本发明所述有机化合物应用于OLED器件中的应用例：
应用例1：本应用例提供一种OLED器件，所述OLED器件的制备方法如下：
(1)用三氯乙烯、丙酮、乙醇和蒸馏水依次对用于有机发光二极管(OLED)器件的玻璃基材上的透明电极氧化铟锡(ITO)薄膜(15Ω/sq，韩国三星康宁公司Samsung Corning)进行超声清洗，然后储存在异丙醇中；将ITO基材安装在真空气相沉积设备的基材夹具上。
(2)将化合物HIL引入真空气相沉积设备的室中，然后对所述设备的室压进行控制以达到10-6托，向室内施加电流以蒸发上述引入的物质，从而在ITO基材上形成厚度为60nm的空穴注入层。
(3)将本发明提供的有机电致化合物H1引入真空气相沉积设备的另一个室中，通过向该室施加电流以进行蒸发，从而在所述空穴注入层上形成厚度为20nm的空穴传输层。
(4)将化合物CBP引入真空气相沉积设备的一个室中作为基质材料，并将化合物D-1引入另一个室中作为掺杂剂；将两种材料以不同的速率进行蒸发，并以15重量％(以基质材料和掺杂剂的总重量为基准计)的掺杂量进行沉积，从而在空穴传输层上形成厚度为30nm的发光层。
(5)将化合物ETL引入一个室中，并将8-羟基喹啉合锂(lithium quinolate)引入另一个室中；将两种材料以相同的速率进行蒸发，并分别以50重量％的掺杂量进行沉积，从而在发光层上形成厚度为30nm的电子传输层。
(6)在电子传输层上沉积了厚度为2nm的8-羟基喹啉合锂作为电子注入层EIL。
(7)通过另一真空气相沉积设备在电子注入层上沉积厚度为150nm的Al阴极；得到所述OLED器件。
上述制备OLED器件所用的所有材料，在使用前通过在10-6托条件下的真空升华进行纯化。
应用例2：本应用例提供一种OLED器件，与应用例1的区别在于：将步骤(3)中的H1替换为H2。
应用例3：本应用例提供一种OLED器件，与应用例1的区别在于：将步骤(3)中的H1替换为H4。
应用例4：本应用例提供一种OLED器件，与应用例1的区别在于：将步骤(3)中的H1替换为H11。
应用例5：本应用例提供一种OLED器件，与应用例1的区别在于：将步骤(3)中的H1替换为H17。
应用例6：本应用例提供一种OLED器件，与应用例1的区别在于：将步骤(3)中的H1替换为H26。
应用例7：本应用例提供一种OLED器件，与应用例1的区别在于：将步骤(3)中的H1替换为H29。
对比例1：本对比例提供一种OLED器件，与应用例1的区别在于：将步骤(3)中的H1替换为HTL(NPB)。
OLED器件的性能测试
使用杭州远方生产的OLED-1000多通道加速老化寿命与光色性能分析系统测试应用例1～7、对比例1提供的OLED器件的驱动电压、电流效率和寿命LT90；其中，LT90是指保持电流密度不变，亮度降至原始亮度90％所需要的时间。
具体测试结果如表1所示：
表1 OLED器件性能检测结果
Figure BDA0002859875010000131
由表1可知，与现有技术中的有机电致发光化合物相比，本发明的有机电致发光化合物具有优异的性质，因而本发明提供的有机电致发光器件具有高发光效率和长工作寿命；并且，该有机电致发光器件需要低驱动电压，从而改善了功率效率和功率消耗。
上述实施例只为说明本发明的技术构思及特点，其目的在于让熟悉此项技术的人士能够了解本发明的内容并据以实施，并不能以此限制本发明的保护范围。凡根据本发明精神实质所作的等效变化或修饰，都应涵盖在本发明的保护范围之内。

Claims (6)

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如式Ⅰ所示结构：
Figure FDA0002859875000000011
其中，Ar1、Ar2各自独立的代表具有C6～C60的芳香族或C6～C60的杂芳香族环系。
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：所述其中Ar1、Ar2各自独立的代表苯、萘、菲、芴、二苯并呋喃或二苯并噻吩咔唑或者它们的组合。
3.根据权利要求1或2所述的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选自式H1～式H30中的一种或多种：
Figure FDA0002859875000000012
Figure FDA0002859875000000021
Figure FDA0002859875000000031
4.一种OLED器件用空穴传输层，其特征在于：所述空穴传输层包括权利要求1～3任一项所述的有机电致发光化合物。
5.一种OLED器件，其特征在于：所述OLED器件包括阳极、阴极以及位于所述阳极和所述阴极之间的至少一层有机薄膜层；所述有机薄膜层包括空穴传输层，还包括空穴注入层、电子阻挡层、空穴阻挡层、发光层、电子传输层和电子注入层中的任意一种或至少两种的组合；
所述空穴传输层为如权利要求4所述的OLED器件用空穴传输层。
6.一种电子设备，其特征在于，所述电子设备包括如权利要求5所述的OLED器件。
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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150077220A (ko) * 2013-12-27 2015-07-07 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
CN105669555A (zh) * 2014-12-05 2016-06-15 乐金显示有限公司 有机发光显示装置
US20180175306A1 (en) * 2016-12-15 2018-06-21 Universal Display Corporation Organic Electroluminescent Materials and Devices
CN108658789A (zh) * 2018-05-16 2018-10-16 上海道亦化工科技有限公司 一种含芴的三芳香胺化合物及其用途和发光器件
CN108727398A (zh) * 2018-06-28 2018-11-02 宁波卢米蓝新材料有限公司 一种稠环化合物及其制备方法和用途
CN109485577A (zh) * 2017-09-13 2019-03-19 东进世美肯株式会社 新颖化合物及包含其的有机发光器件
WO2020091446A1 (en) * 2018-10-31 2020-05-07 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compound and organic electroluminescent device comprising the same
CN111566186A (zh) * 2018-01-19 2020-08-21 罗门哈斯电子材料韩国有限公司 有机电致发光化合物和包含其的有机电致发光装置

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150077220A (ko) * 2013-12-27 2015-07-07 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
CN105669555A (zh) * 2014-12-05 2016-06-15 乐金显示有限公司 有机发光显示装置
US20180175306A1 (en) * 2016-12-15 2018-06-21 Universal Display Corporation Organic Electroluminescent Materials and Devices
CN109485577A (zh) * 2017-09-13 2019-03-19 东进世美肯株式会社 新颖化合物及包含其的有机发光器件
CN111566186A (zh) * 2018-01-19 2020-08-21 罗门哈斯电子材料韩国有限公司 有机电致发光化合物和包含其的有机电致发光装置
CN108658789A (zh) * 2018-05-16 2018-10-16 上海道亦化工科技有限公司 一种含芴的三芳香胺化合物及其用途和发光器件
CN108727398A (zh) * 2018-06-28 2018-11-02 宁波卢米蓝新材料有限公司 一种稠环化合物及其制备方法和用途
WO2020091446A1 (en) * 2018-10-31 2020-05-07 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compound and organic electroluminescent device comprising the same

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