CN110143885A - 一种具有螺二芴结构的有机化合物及其应用 - Google Patents

一种具有螺二芴结构的有机化合物及其应用 Download PDF

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CN110143885A
CN110143885A CN201910440947.7A CN201910440947A CN110143885A CN 110143885 A CN110143885 A CN 110143885A CN 201910440947 A CN201910440947 A CN 201910440947A CN 110143885 A CN110143885 A CN 110143885A
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organic compound
organic
compound
spiral shell
fluorenes
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李仲庆
杭德余
梁现丽
段陆萌
班全志
李继响
程丹丹
曹占广
黄春雪
罗忠林
刘阳
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Beijing Yanshan Gicom Photoelectric Technology Co Ltd
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Beijing Yanshan Gicom Photoelectric Technology Co Ltd
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Abstract

本发明涉及一种具有螺二芴结构的有机化合物，其具有如通式I所示的结构。上述有机化合物以螺二芴为主体，从而可以提高玻璃化温度，分子热稳定性强，具有合适的HOMO和LUMO能级和较高的Eg，可以有效地提升光电性能以及OLED器件寿命。同时引入芳胺类基团，与单纯的螺二芴相比具有更好的平面结构和共轭体系，合成、提纯比较简单，成本低廉，同时苯环上含有甲基，从而可以增大分子间的距离，防止化合物之间的缔合，降低了分子的堆砌的几率。蒸镀时不容易发生结晶化，应用到OLED器件中可有效提高OLED成品率，可以有效地提高发光效率，成膜性好。该材料也可以作为发光材料使用，能有效提高发光材料的寿命。

Description

一种具有螺二芴结构的有机化合物及其应用
技术领域
本发明涉及有机电致发光显示技术领域，具体涉及一种新型有机材料及其在有机电致发光器件中的应用。
背景技术
有机电致发光(OLED)材料在信息显示材料、有机光电子材料等领域中的应用具有极大的研究价值和美好的应用前景。随着多媒体信息技术的发展，对平板显示器件性能的要求越来越高。目前主要的显示技术有等离子显示器件、场发射显示器件和有机电致发光显示器件(OLED)。其中，OLED具有自身发光、低电压直流驱动、全固化、视角宽、颜色丰富等一系列优点，与液晶显示器件相比，OLED不需要背光源，视角更宽，功耗低，其响应速度是液晶显示器件的1000倍，因此，OLED具有更广阔的应用前景。
目前报道的有机空穴传输材料由于分子量普遍较小，材料的玻璃化温度较低，在材料使用过程中，反复充电放电，材料容易结晶，薄膜的均一性被破坏，从而影响材料使用寿命。因此，开发稳定高效的有机空穴传输材料，从而降低驱动电压，提高器件发光效率，延长器件寿命，具有很重要的实际应用价值。
发明内容
本发明的目的在于提供可进行低电压驱动、长寿命并且已高效率化的OLED元件，以及可提供这样的OLED元件的化合物。
为了开发具有前述性质的化合物及使用了此类化合物的OLED元件，结果发现，通过利用通式I表示的化合物，可达到上述目的。即，本发明提出了一种新型的有机材料，其具有如通式I所示结构：
所述通式I中，m代表苯环上甲基的取代个数，可选自1、2或3。具体而言，1、2或3个甲基可取代式I’所示结构的1、2、3和/或4号位置上的氢原子。
当m＝1时，甲基可取代式I’所示结构的1、2、3或4号任意一个位置上的氢原子，即所述有机材料可选自如式I’-1～I’-4所示的结构，优选为如式I’-2所示的结构。
当m＝2时，甲基可取代式I’所示结构的1、2、3和/或4号任意两个位置上的氢原子，即所述有机材料可选自如式I’-5～I’-10所示的结构。
当m＝3时，甲基可取代式I’所示结构的1、2、3和/或4号任意三个位置上的氢原子，即所述有机材料可选自如式I’-11～I’-14所示的结构。
所述通式I中Ar1、Ar2各自独立地代表含有n个苯环和/或芳杂环的芳香基团。所述芳香基团可以是取代或未取代的单环芳烃，也可以是取代或未取代的多环芳烃；所述多环芳烃可以是多苯代脂烃、联苯型多环芳烃或稠环芳烃。所述n代表1、2、3、4或5。
所述Ar1、Ar2各自代表的基团可以相同，也可以不同。
本发明对Ar1、Ar2代表的基团进行优选，以进一步提高材料的综合性能。具体而言：
本发明优选所述n代表1、2、3或4，Ar1、Ar2各自独立地选自如下具体基团：
更优选地，Ar1、Ar2各自独立地选自如下具体基团：
进一步优选地，所述n代表2、3或4，Ar1、Ar2各自独立地选自如下具体基团：
上述各优选方案中，Ar1、Ar2代表的基团可以相同，也可以不同。
作为本发明的一种具体优选方案，所述Ar1选自如下基团：
作为本发明的一种具体优选方案，所述Ar2选自如下基团：
上述各取代基团中，表示取代位。
本发明进一步优选通式I所示有机材料选自如下通式I-1～I-55所示的化合物：
所述通式I-1～I-55中，m各自独立地代表1、2或3，甲基的具体取代方式如上文所述。
上述有机化合物以螺二芴为主体，从而可以提高玻璃化温度，分子热稳定性强，具有合适的HOMO和LUMO能级和较高的Eg，可以有效地提升光电性能以及OLED器件寿命。同时引入芳胺类基团，与单纯的螺二芴相比具有更好的平面结构和共轭体系，合成、提纯比较简单，成本低廉，同时苯环上含有甲基，从而可以增大分子间的距离，防止化合物之间的缔合，降低了分子的堆砌的几率。蒸镀时不容易发生结晶化，应用到OLED器件中可有效提高OLED成品率，可以有效地提高发光效率，成膜性好。该材料也可以作为发光材料使用，能有效提高发光材料的寿命。
本发明同时提供了通式I所示有机化合物的制备方法。
所述制备方法的反应历程如下:
所述制备方法以含甲基螺二芴一溴取代基类化合物A为起始原料，与发生偶联反应，得到最终目标化合物I。
上述的步骤本领域技术人员可采用已知的常见手段来实现，如选择合适的催化剂，溶剂，确定适宜的反应温度，时间等，本发明对此不作特别限定。
作为本发明的一种优选方案，所述具体制备方法包括如下步骤：
以甲苯为溶剂，以乙酸钯和三叔丁基膦为催化剂，叔丁醇钾为碱，在氮气保护、控温80～120℃的条件下，含甲基螺二芴一溴取代基类化合物与发生偶联反应，得到最终目标化合物I。
上述溶剂、催化剂、碱等原料均可以通过公开商业途径或者本领域已知的方法合成得到。
本发明进一步提供了通式I所示的有机化合物在有机电致发光器件中的应用。本发明优选所述有机化合物在有机电致发光器件中用作空穴传输层的空穴传输材料。
本发明还提供了一种有机电致发光器件，其有机功能层中包括本发明通式I所示的有机化合物。本发明优选所述有机化合物用作有机功能层中空穴传输层的空穴传输材料。所述空穴传输层的厚度可以为10～50nm，优选为27～33nm。
作为本发明的一种优选方案，上述有机电致发光器件由下至上依次包括透明基片、阳极层、通式I所示的有机化合物构成的空穴传输层、电致发光层、电子传输层、电子注入层和阴极层。
其中，构成所述透明基片的材料可选用玻璃基片或柔性基片，具体可以使用传统有机发光器件中的基板，例如玻璃基板或塑料基板，优选用玻璃基板。
构成所述阳极层的材料可选用无机材料，具体可选用氧化铟锡(ITO)、氧化锌、氧化锡锌、金、银或铜中的至少一种，优选氧化铟锡(ITO)。
构成所述电致发光层的主体材料可以选自如下化合物中的任意一种，优选为CBP(4,4'-N,N'-二咔唑-联苯)：
构成所述电致发光层的材料中还可以添加掺杂剂，如(piq)2Ir(acac)[二-(1-苯基异喹啉基)乙酰丙酮铱(III)]。
构成所述电子传输层的材料可以选自如下化合物中的任意一种：
构成所述电子注入层的材料可以选自LiF、Li2O、MgO、Al2O3中的一种，优选为LiF。
构成所述阴极的材料选可以自锂、镁、银、钙、锶、铝、铟、铜、金和银中的一种，优选铝。
为了确保所述发光器件内各层的材料之间发挥协同作用，本发明还对所述发光器件内各层的厚度进行优选，以使得所述发光器件发挥最佳的综合效果。
具体而言，所述空穴传输层的厚度可以为10～50nm，优选为27～33nm；所述电致发光层的厚度可以为10～100nm，优选为27～33nm；所述电子传输层的厚度可以为10～30nm，优选为18～22nm；所述电子注入层的厚度可以为5-～30nm，优选为9～11nm；所述阴极层的厚度可以为50～200nm，优选为100～200nm。
本发明提供的新型OLED材料以9,9’螺二芴为主体，以胺类化合物为端基，通过在多环芳香族化合物的活泼位置，引入具有空穴传输性能的芳胺类取代基团，获得了一类具有空穴传输性能的新型OLED材料。该类材料具有高的空穴迁移率，较好的薄膜稳定性和适合的分子能级，高的发光效率，可以被应用在有机电致发光领域，作为空穴传输材料使用。
具体实施方式
以下实施例用于说明本发明，但不用来限制本发明的范围。
下面阐述本发明中部分主要化合物的合成方法。
实施例1
合成路线如下：
包括如下具体步骤：
500毫升三口瓶，配磁力搅拌，氩气置换后依次加入叔丁醇钾18.1g(0.188mol)、N-([1,1’-联苯]-4-基)-9H-芴-2-胺33.34g(纯度99％，0.1mol)和甲苯100ml。再次氮气置换后依次加入1.6ml三叔丁基膦和0.23g乙酸钯。加完后，加热升温至85℃。开始滴加在由48.82g含甲基螺二芴一溴取代基类化合物(A-2-2)(纯度99％，0.1mol)和100ml甲苯组成的溶液，控温80-120℃。降温至50℃，加入100m去离子水水解，搅拌10分钟，过滤，滤饼用DMF反复煮沸几次，旋蒸得到65.92g白色固体，纯度99％，收率89％。
产物MS(m/e)：661.83；元素分析(C51H35N)：理论值C：92.55％，H：5.33％，N：2.12％；实测值C：92.54％，H：5.34％，N：2.12％。
实施例2
合成路线如下：
500毫升三口瓶，配磁力搅拌，氩气置换后依次加入叔丁醇钾18.1g(0.188mol)、N-二苯并[b，d]噻吩-5-(对甲苯基)吡啶-2-胺36.65g(纯度99％，0.15mol)和甲苯100ml。再次氮气置换后依次加入1.6ml三叔丁基膦和0.23g乙酸钯。加完后，加热升温至85℃。开始滴加在由10.93g含甲基螺二芴一溴取代基类化合物(A-31-2)(纯度99％，0.1mol)和100ml甲苯组成的溶液，控温80-120℃。降温至50℃，加入100m去离子水水解，搅拌10分钟，过滤，滤饼用DMF反复煮沸几次，得到61.15g白色产物，纯度99％，产率88％。
产物MS(m/e)：694.88；元素分析(C50H34N2S)：理论值C：86.42％，H：4.93％，N：4.03％，S：4.61％；实测值C：86.40％，H：4.95％，N：4.03％，S：4.61％。
实施例3
合成路线如下：
500毫升三口瓶，配磁力搅拌，氩气置换后依次加入叔丁醇钾18.1g(0.188mol)、N-(5-(对-甲苯基)吡啶-2-基)异喹啉-7-胺31.13g(纯度99％，0.15mol)和甲苯100ml。再次氮气置换后依次加入1.6ml三叔丁基膦和0.23g乙酸钯。加完后，加热升温至85℃。开始滴加在由40.93g含甲基螺二芴一溴取代基类化合物(A-55-2)(纯度99％，0.1mol)和100ml甲苯组成的溶液，控温80-120℃。降温至50℃，加入100m去离子水水解，搅拌10分钟，过滤，滤饼用DMF反复煮沸几次，得到57.90g白色固体，纯度99％，产率90.5％。
产物MS(m/e)：739.79；元素分析(C47H33N3)：理论值C：88.23％，H：5.20％，N：6.57％；实测值C：88.22％，H：5.21％，F：N：6.57％。
试验过程中所用中间体N-([1,1’-联苯]-4-基)-9H-芴-2-胺等均可从北京燕化集联光电技术有限公司购买所得。
依据实施例1、实施例2和实施例3的技术方案，只需要简单替换对应的原料，不改变任何实质性操作，可以合成以下化合物。
实施例4：OLED器件
本实施例提供了一组OLED器件，制备方法具体为：
(1)将涂布了ITO导电层的玻璃基片在清洗剂中超声处理30分钟，在去离子水中冲洗，在丙酮/乙醇混合溶剂中超声30分钟，在洁净的环境下烘烤至完全干燥，用紫外光清洗机照射10分钟，并用低能阳离子束轰击表面；
(2)把上述处理好的ITO玻璃基片置于真空腔内，抽真空至1×10-5～9×10-4Pa在上述阳极层膜上真空蒸镀化合物2-TNATA，形成厚度为60nm的空穴注入层；在空穴注入层之上真空蒸镀实施例1提供的化合物I-2-2作为空穴传输层，蒸镀速率为0.2nm/s，蒸镀膜厚为30nm；
(3)在上述空穴传输层上形成电致发光层，具体操作为：将作为发光层主体材料CBP[4,4'-N,N'-二咔唑-联苯]放置在真空气相沉积设备的小室中，将作为掺杂剂的(piq)2Ir(acac)[二-(1-苯基异喹啉基)乙酰丙酮铱(III)]放置在真空气相沉积设备的另一室中，以不同的速率同时蒸发两种材料，(piq)2Ir(acac)的浓度为5％，蒸镀总膜厚为30nm；
(4)在所述电致发光层上继续蒸镀一层化合物BCP作为器件的电子传输层，蒸镀速率为0.2nm/s，蒸镀膜厚为20nm；所述BCP的结构为：
(5)在所述电子传输层之上继续蒸镀一层LiF作为器件的电子注入层，蒸镀速率为0.2nm/s，蒸镀膜厚为10nm；
(6)在所述电子注入层之上继续蒸镀一层Al作为器件的阴极，蒸镀速率为0.2nm/s，蒸镀膜厚为150nm；得到本发明提供的OLED器件，记为OLED-1。
按照与上相同的步骤，仅将步骤(2)中的化合物I-2-2替换为实施例2提供的化合物I-31-2，得到本发明提供的OLED-2。
按照与上相同的步骤，仅将步骤(2)中的化合物I-2-2替换为实施例3提供的化合物I-55-2，得到本发明提供的OLED-3。
按照与上相同的步骤，仅将步骤(2)中的化合物I-2-2替换为NPB(对比化合物1)，得到本发明提供的OLED-4。所述NPB的结构具体为：
本发明对上述所得器件OLED-1～OLED-4的性能进行检测，检测结果如表1所示。
表1：OLED器件性能检测结果
由上可知，利用本发明提供的式I所示有机材料制备成的器件OLED-1、OLED-2以及OLED-3的工作电压更低，且在亮度相同的条件下，电流效率明显比NPB作为空穴传输材料的器件OLED-4高很多。
虽然，上文中已经用一般性说明、具体实施方式及试验，对本发明作了详尽的描述，但在本发明基础上，可以对之作一些修改或改进，这对本领域技术人员而言是显而易见的。因此，在不偏离本发明精神的基础上所做的这些修改或改进，均属于本发明要求保护的范围。

Claims (10)

1.一种具有螺二芴结构的有机化合物，其特征在于，具有如通式I所示的结构：
所述通式I中，m为1～3的整数；
Ar1、Ar2各自独立地代表含有n个苯环和/或芳杂环的芳香基团，n为1～5的整数，优选为1、2、3或4，更优选为2、3或4。
2.根据权利要求1所述的有机化合物，其特征在于，Ar1、Ar2各自独立地选自如下基团：
3.根据权利要求1～2任意一项所述的有机化合物，其特征在于，Ar1、Ar2各自独立地选自如下基团：
4.根据权利要求1～3任意一项所述的有机化合物，其特征在于，Ar1、Ar2各自独立地选自如下基团：
5.根据权利要求1～4任意一项所述的有机化合物，其特征在于，所述Ar1选自如下基团：
6.根据权利要求1～5任意一项所述的有机化合物，其特征在于，所述Ar2选自如下基团：
7.根据权利要求1所述的有机化合物，其特征在于，选自如下通式I-1～I-55所示的化合物：
8.权利要求1～7任意一项所述有机化合物的制备方法，其特征在于，反应历程如下:
所述方法以含甲基螺二芴一溴取代基类化合物为起始原料，与发生偶联反应，得到最终目标化合物I；
优选地，所述方法包括如下步骤：
以甲苯为溶剂，以乙酸钯和三叔丁基膦为催化剂，叔丁醇钾为碱，在氮气保护、控温80～120℃的条件下，含甲基螺二芴一溴取代基类化合物与发生偶联反应，得到最终目标化合物I。
9.权利要求1～7任意一项所述有机化合物在有机电致发光器件中的应用；
优选地，所述有机化合物在有机电致发光器件中用作空穴传输层的空穴传输材料。
10.一种有机电致发光器件，其有机功能层中包括权利要求1～7任意一项所述的有机化合物；
优选地，所述有机化合物用作有机功能层中空穴传输层的空穴传输材料；
更优选地，所述空穴传输层的厚度为10～50nm。
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