CN111662188A - 一种以含有芘或者氮杂芘的三芳胺为核心的化合物及其应用 - Google Patents
一种以含有芘或者氮杂芘的三芳胺为核心的化合物及其应用 Download PDFInfo
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- CN111662188A CN111662188A CN201910177314.1A CN201910177314A CN111662188A CN 111662188 A CN111662188 A CN 111662188A CN 201910177314 A CN201910177314 A CN 201910177314A CN 111662188 A CN111662188 A CN 111662188A
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 title claims abstract description 14
- QHADMMAFBAZFTE-UHFFFAOYSA-N naphtho[2,1,8-def]quinoline Chemical compound C1=CN=C2C=CC3=CC=CC4=CC=C1C2=C43 QHADMMAFBAZFTE-UHFFFAOYSA-N 0.000 title claims abstract description 14
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- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
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- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
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Abstract
Description
技术领域
本发明涉及半导体材料技术领域,尤其是涉及一种以含有芘或者氮杂芘的三芳胺为核心的化合物及其在有机电致发光器件上的应用。
背景技术
当前,OLED显示技术已经在智能手机,平板电脑等领域获得应用,进一步还将向电视等大尺寸应用领域扩展,但是,和实际的产品应用要求相比,OLED器件的发光效率和使用寿命等性能还需要进一步提升。目前对OLED发光器件提高性能的研究包括:降低器件的驱动电压、提高器件的发光效率、提高器件的使用寿命等。为了实现OLED器件的性能的不断提升,不但需要从OLED器件结构和制作工艺的创新,更需要OLED光电功能材料不断研究和创新,创制出更高性能的OLED功能材料。
应用于OLED器件的OLED光电功能材料从用途上可划分为两大类,分别为电荷注入传输材料和发光材料。进一步,还可将电荷注入传输材料分为电子注入传输材料、电子阻挡材料、空穴注入传输材料和空穴阻挡材料,还可以将发光材料分为主体发光材料和掺杂材料。
为了制作高性能的OLED发光器件,要求各种有机功能材料具备良好的光电性能,譬如,作为电荷传输材料,要求具有良好的载流子迁移率,高玻璃化转化温度等,作为发光层的主体材料具有良好双极性,适当的HOMO/LUMO能阶等。
构成OLED器件的OLED光电功能材料膜层至少包括两层以上结构,产业上应用的OLED器件结构则包括空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层等多种膜层,也就是说应用于OLED器件的光电功能材料至少包括空穴注入材料、空穴传输材料、发光材料、电子传输材料等,材料类型和搭配形式具有丰富性和多样性的特点。另外,对于不同结构的OLED器件搭配而言,所使用的光电功能材料具有较强的选择性,相同的材料在不同结构器件中的性能表现也可能完全迥异。
因此,针对当前OLED器件的产业应用要求以及OLED器件的不同功能膜层,器件的光电特性需求,必须选择更适合、性能更高的OLED功能材料或材料组合,才能实现器件的高效率、长寿命和低电压的综合特性。就当前的OLED显示照明产业的实际需求而言,目前OLED材料的发展还远远不够,落后于面板制造企业的要求,作为材料企业开发更高性能的有机功能材料显得尤为重要。
发明内容
针对现有技术存在的上述问题,本发明申请人提供了一种以含有芘或者氮杂芘的三芳胺为核心的化合物及其应用。本发明化合物以含有芘或者氮杂芘的三芳胺为核心,具有较高的玻璃化转变温度和分子热稳定性,合适的HOMO能级,通过器件结构优化,可有效提升OLED器件的光电性能以及OLED器件的寿命。
本发明的技术方案如下:一种以含有芘或者氮杂芘的三芳胺为核心的化合物,所述化合物的结构如通式(1)所示:
通式(1)中,,n表示为数字0或1;
n表示为数字0时,意味着L1和L2直接相连;
L1、L2、L3各自独立的表示为单键、亚苯基或亚萘基;
Y每次出现相同或不同的表示为C-R或氮原子,其中,R每次出现相同或不同的表示为氢原子、氘原子、取代或未取代的C1-10烷基、取代或未取代的C6-30芳基或者取代或未取代的C3-30杂芳基;
Ar1表示为苯基或萘基;
Ar2表示为取代或未取代的C6-30芳基;
Ar3表示为通式(2)所示结构
所述通式(2)中,X表示为-O-、-S-、-C(R1)(R2)-或-N(R3)-;
Z每次出现相同或不同的表示为C-R、碳原子或氮原子,与其它基团相连的Z表示为碳原子,其中,R每次出现相同或不同的表示为氢原子、氘原子、取代或未取代的C1-10烷基、取代或未取代的C6-30芳基或取代或未取代的C3-30杂芳基;
所述R1、R2以及R3各自独立的表示为C1-10的烷基、取代或未取代的C6-30芳基、取代或未取代的C3-30杂芳基;且R1与R2可相互键结成环;
上述各基团被取代时的取代基选自氟原子、氰基、苯基、联苯基、萘基、呋喃基、咔唑基、噻吩基或吡啶基中的一种或多种;
所述杂芳基中的杂原子选自N、O或S中的一种或多种。
进一步,所述通式(1)中至少有一个Y表示为氮原子。
进一步,所述通式(2)中至少有一个Z表示为氮原子。
进一步的,所述R优选氢、氘、甲基、异丙基、叔丁基、环己基、取代或未取代的苯基、取代或未取代的萘基、取代或未取代的吡啶基中的一种;
其中R1~R3各自独立的任选自甲基、乙基、丙基、异丙基、丁基、叔丁基、戊基、己基、环己基、取代或未取代的苯基、取代或未取代联苯基、取代或未取代的萘基、取代或未取代的吡啶基中的一种;
上述各基团被取代时的取代基选自氟原子、氰基、苯基、联苯基、萘基、呋喃基、咔唑基、噻吩基或吡啶基中的一种或多种。
优选方案,所述化合物表示为通式(1-1)、通式(1-2)、通式(1-3)、通式(1-4)、通式(1-5)、通式(1-6)、通式(1-7)或通式(1-8)所示结构中任一种;
优选方案,所述通式(1)为下列具体化合物中的任一种:
一种有机电致发光器件,所述有机电致发光器件的阳极与阴极之间具有多层有机薄膜层,至少一层有机薄膜层含有所述以含有芘或者氮杂芘的三芳胺为核心的化合物。
作为本发明的进一步改进,所述多层有机薄膜层包括电子阻挡层和/或空穴传输层,所述电子阻挡层和/或空穴传输层含有所述以含有芘或者氮杂芘的三芳胺为核心的化合物。
一种显示元件,所述显示元件含有所述的有机电致发光器件。
另外说明,本发明申请C1-20烷基优选下列基团:甲基、乙基、正丙基、异丙基、正丁基、异丁基、1-甲基丙基、叔丁基、正戊基、异戊基、1-乙基丙基、1-甲基丁基、2-甲基丁基、3-甲基丁基、正己基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基。
在本发明的上下文中,杂芳基为单环或双环芳族杂环(杂芳族),其含有最多达四个选自N、O和S的相同或不同的环杂原子,并且经由环碳原子或如果合适,经由环氮原子连接,优选下列基团:呋喃基、吡咯基、噻吩基、吡唑基、咪唑基、喹啉基、噻唑基、噁唑基、异噁唑基、异噻唑基、三唑基、噁二唑基、噻二唑基、四唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基和三嗪基。
当本发明化合物中的基团被取代时,所述基团可被单取代或多取代,除非另有说明。
与现有技术相比,本发明有益的技术效果在于:
(1)本发明的化合物以含有芘或者氮杂芘的三芳胺为核心,连接给电子基团,具有较高的空穴迁移率,作为OLED发光器件的空穴传输层的材料,可提高激子在发光层中的复合效率,提高能量利用率,从而提高器件发光效率。
(2)本发明的化合物使得电子和空穴在发光层的分布更加平衡,在恰当的HOMO能级下,提升了空穴注入和传输性能;在合适的LUMO能级下,又起到了电子阻挡的作用,提升激子在发光层中的复合效率;可有效提高激子利用率,降低器件电压,提高器件的电流效率和寿命。本发明的化合物在OLED发光器件中具有良好的应用效果,具有良好的产业化前景。
附图说明
图1为本发明所列举的材料应用于OLED器件的结构示意图;
图中,1为透明基板层,2为ITO阳极层,3为空穴注入层,4、空穴传输层,5为电子阻挡层,6为发光层,7为电子传输层,8为电子注入层,9为阴极层,10为CPL层。
图2为本发明器件的电流效率随温度的变化曲线。
图3为本发明化合物274的UV吸收光谱;
图4为本发明化合物426的UV吸收光谱。
具体实施方式
下面结合附图和实施例,对本发明进行具体描述。
下述实施例中所有反应物均采购于烟台万润精细化工股份有限公司。
实施例1化合物003的合成:
将0.01mol反应物A-1和0.012mol反应物B-1溶解于150mL甲苯中,加入0.015mol的叔丁醇钾,0.001molCuI,在氮气的氛围下120℃反应24小时,取样点板,待反应完全后,冷却、过滤,将滤液旋蒸除去溶剂,粗产品过硅胶柱,得到化合物1,收率79.5%,HPLC纯度99.65%;元素分析结构(C67H47N)理论值:C,92.91;H,5.47;N,1.62;测试值:C,92.90;H,5.46;N,1.64。HRMS(EI):理论值为865.3709,实测值为865.3722。
其中反应物A-1的合成步骤为:
将0.01mol的1-芘硼酸与0.012mol的卤代化合物加至150mL的甲苯:乙醇=2:1的混合溶剂中,加入0.02mol的碳酸钾,除氧后加入0.0002mol Pd(PPh3)4,在氮气的氛围下110℃反应24小时,取样点板,待反应物反应完全后,冷却、过滤,将滤液旋蒸除去溶剂,粗产品过硅胶柱,得到反应物A-1;HPLC纯度98.97%,收率74.5%;元素分析结构(C34H21Br)理论值:C,80.16;H,4.16;Br,15.68;测试值:C,80.19;H,4.15;Br,15.66。HRMS(EI):理论值:508.0827,实测值:508.0809。
上述卤代化合物可通过芳基卤代物与苯基硼酸的铃木偶联反应1-2步合成得到。
重复实施例1制备过程合成以下化合物;反应条件相同,不同之处在于使用下表1中所列出的反应物A和反应物B;
表1
本发明的有机化合物在发光器件中使用,可以作为电子阻挡层或空穴传输层材料使用。对本发明化合物(003)、化合物(013)、化合物(016)、化合物(037)、化合物(045)、化合物(057)、化合物(064)、化合物(081)、化合物(082)、化合物(099)、化合物(142)、化合物(151)、化合物(159)、化合物(201)、化合物(218)、化合物(229)、化合物(237)、化合物(248)、化合物(274)、化合物(276)、化合物(300)、化合物(312)、化合物(334)、化合物(346)、化合物(347)、化合物(371)、化合物(379)、化合物(414)、化合物(426)、化合物(437)、化合物(444)、化合物(452)、化合物(468)、化合物(477)、化合物(486)和化合物(496)分别进行热性能、Eg、HOMO能级以及空穴迁移率的检测,结果如表2所示。
表2
注:玻璃化温度Tg由示差扫描量热法(DSC,德国耐驰公司DSC204F1示差扫描量热仪)测定,升温速率10℃/min;热失重温度Td是在氮气气氛中失重1%的温度,在日本岛津公司的TGA-50H热重分析仪上进行测定,氮气流量为20mL/min;最高占据分子轨道HOMO能级是由电离能量测试系统(IPS3)测试,测试为大气环境。空穴迁移率:将材料制作成单电荷器件,用SCLC方法测定。使用Gaussian16,采用TD-FDT算法优化几何结构,6-31G(d)基组,B3lyp泛函,进行HOMO、LUMO能级计算,Eg=|HOMO-LUMO|;Eg实测通过紫外光谱进行测试;
由上表数据可知,本发明的有机化合物具有高的玻璃转化温度,可提高材料膜相态稳定性,进一步提高器件使用寿命;具有高的T1能级,可以阻挡发光层能量损失,从而提升器件发光效率;合适的HOMO能级可以解决载流子的注入问题,可降低器件电压,较高的带隙宽度(Eg),保证材料在可见光领域范围内没有吸收。因此,本发明含芘的化合物在应用于OLED器件的不同功能层后,可有效提高器件的发光效率及使用寿命。
以下通过器件实施例1-36和器件比较例1详细说明本发明合成的化合物在器件中作为空穴传输材料的应用效果。器件实施例2-36以及器件比较例1与器件实施例1相比,所述器件的制作工艺完全相同,并且采用了相同的基板材料和电极材料,电极材料的膜厚也保持一致,所不同的是器件中空穴传输层材料发生了改变。器件叠层结构如表3所示,各器件的性能测试结果见表4和表5。
器件实施例1
透明基板层1/ITO阳极层2/空穴注入层3(HAT-CN,厚度10nm)/空穴传输层4(化合物(003),厚度60nm)/电子阻挡层5(EB-1,厚度20nm)/发光层6(GH1、GH2和GD-1按照45:45:10的重量比混掺,厚度40nm)/空穴阻挡/电子传输层7(ET-1和Liq,按照1:1的重量比混掺,厚度40nm)/电子注入层8(LiF,厚度1nm)/阴极层9(Mg和Ag,按照9:1的重量比混掺,厚度15nm)/CPL层10(化合物CP-1,厚度70nm)。
具体制备过程如下:
如图1所示,透明基板层1为透明PI膜,对ITO阳极层2(膜厚为150nm)进行洗涤,即依次进行碱洗涤、纯水洗涤、干燥,再进行紫外线-臭氧洗涤以清除透明ITO表面的有机残留物。在进行了上述洗涤之后的ITO阳极层2上,利用真空蒸镀装置,蒸镀膜厚为10nm的HAT-CN作为空穴注入层3使用。接着蒸镀60nm厚度的化合物(003)作为空穴传输层4。随后蒸镀20nm厚度的EB-1作为电子阻挡层5。上述空穴传输材料蒸镀结束后,制作OLED发光器件的发光层6,其结构包括OLED发光层6所使用GH-1、GH-2作为主体材料,GD-1作为掺杂材料,掺杂材料掺杂比例为10%重量比,发光层膜厚为40nm。在上述发光层6之后,继续真空蒸镀电子传输层材料为ET-1和Liq。该材料的真空蒸镀膜厚为40nm,此层为空穴阻挡/电子传输层7。在空穴阻挡/电子传输层7上,通过真空蒸镀装置,制作膜厚为1nm的氟化锂(LiF)层,此层为电子注入层8。在电子注入层8上,通过真空蒸镀装置,制作膜厚为15nm的Mg:Ag电极层,此层为阴极层9使用。在阴极层9上,真空蒸镀70nm的CP-1,作为CPL层10。如上所述地完成OLED发光器件后,用公知的驱动电路将阳极和阴极连接起来,测量器件的电流效率以及器件的寿命。
按照上述步骤完成电致发光器件的制作后,测量器件的效率数据和光衰寿命,其结果见表4所示。相关材料的分子结构式如下所示:
表3
各器件实施例和器件比较例1的效率和寿命数据见表4所示。
表4
由表4的器件数据结果可以看出,本发明的有机发光器件无论是效率还是寿命均相对于已知材料的OLED器件获得较大的提升。
进一步的本发明材料制备的OLED器件在低温下工作时效率也比较稳定,将器件实施例1、18、26、35和器件比较例1在-10~80℃区间进行效率测试,所得结果如表5和图2所示。
表5
从表5和图2的数据可知,器件实施例1、18、26、35为本发明材料和已知材料搭配的器件结构,与器件比较例1相比,不仅低温效率高,而且在温度升高过程中,效率平稳升高。
Claims (9)
1.一种以含有芘或者氮杂芘的三芳胺为核心的化合物,其特征在于,所述化合物的结构如通式(1)所示:
通式(1)中,n表示为数字0或1;
L1、L2、L3各自独立的表示为单键、亚苯基或亚萘基;
Ar1表示为苯基或萘基;
Ar2表示为取代或未取代的C6-30芳基;
Ar3表示为通式(2)所示结构
所述通式(2)中,X表示为-O-、-S-、-C(R1)(R2)-或-N(R3)-;
Y每次出现相同或不同的表示为C-R或氮原子;
Z每次出现相同或不同的表示为C-R、碳原子或氮原子,与其它基团相连的Z表示为碳原子;
所述R每次出现相同或不同的表示为氢原子、氘原子、取代或未取代的C1-10烷基、取代或未取代的C6-30芳基或者取代或未取代的C3-30杂芳基;
所述R1、R2以及R3各自独立的表示为C1-10的烷基、取代或未取代的C6-30芳基、取代或未取代的C3-30杂芳基;且R1与R2可相互键结成环;
上述各基团被取代时的取代基选自氟原子、氰基、苯基、联苯基、萘基、呋喃基、咔唑基、噻吩基或吡啶基中的一种或多种;
所述杂芳基中的杂原子选自N、O或S中的一种或多种。
2.根据权利要求1所述的化合物,其特征在于,所述通式(1)中至少有一个Y表示为氮原子。
3.根据权利要求1或2所述的化合物,其特征在于,所述通式(2)中至少有一个Z表示为氮原子。
4.根据权利要求1所述的化合物,其特征在于,所述R优选氢、氘、甲基、异丙基、叔丁基、环己基、取代或未取代的苯基、取代或未取代的萘基、取代或未取代的吡啶基中的一种;
其中R1~R3各自独立的任选自甲基、乙基、丙基、异丙基、丁基、叔丁基、戊基、己基、环己基、取代或未取代的苯基、取代或未取代联苯基、取代或未取代的萘基、取代或未取代的吡啶基中的一种;
上述各基团被取代时的取代基选自氟原子、氰基、苯基、联苯基、萘基、呋喃基、咔唑基、噻吩基或吡啶基中的一种或多种。
7.一种有机电致发光器件,所述有机电致发光器件的阳极与阴极之间具有多层有机薄膜层,其特征在于,至少一层有机薄膜层含有权利要求1~6任一项所述以含有芘或者氮杂芘的三芳胺为核心的化合物。
8.根据权利要求7所述有机电致发光器件,其特征在于,所述多层有机薄膜层包括电子阻挡层和/或空穴传输层,所述电子阻挡层和/或空穴传输层含有权利要求1~6任一项所述以含有芘或者氮杂芘的三芳胺为核心的化合物。
9.一种显示元件,其特征在于,所述显示元件含有权利要求7或8任一项所述的有机电致发光器件。
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