CN117447414A - 一种具有电子传输功能的材料及其应用 - Google Patents
一种具有电子传输功能的材料及其应用 Download PDFInfo
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- CN117447414A CN117447414A CN202311350707.0A CN202311350707A CN117447414A CN 117447414 A CN117447414 A CN 117447414A CN 202311350707 A CN202311350707 A CN 202311350707A CN 117447414 A CN117447414 A CN 117447414A
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- 150000002240 furans Chemical class 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 238000006138 lithiation reaction Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 238000001126 phototherapy Methods 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明提供一种具有电子传输功能的材料及其应用,所述具有电子传输功能的材料具有化学式I所示结构,包含带有取代基的9‑烷基‑9‑芳基芴基团(或含氮的杂芳基)和含氮六元环,其HOMO能级在适度范围内,可有效调控功能层间的势垒,利于电子传输,使迁移率加快,可作为有机电致发光器件的电子传输层材料或空穴阻挡层材料,实现低驱动电压、高发光效率和长使用寿命特性。
Description
技术领域
本发明属于有机电致发光领域,涉及一种具有电子传输功能的材料及其应用。
背景技术
有机发光器件通过向有机电致发光材料施加电力而将电能转换为光,并且通常包括阳极、阴极以及阳极和阴极两个电极之间或两个电极外侧形成的有机物层。有机物层可以包含空穴注入层、空穴传输层、发光辅助层、电子阻挡层、发光层、电子缓冲层、空穴阻挡层、电子传输层、电子注入层、覆盖层等。
电子传输层能避免由阴极和发光层直接接触而引起的发光猝灭。空穴阻挡层会提高器件发光层界面处电子和空穴再结合的概率,增大器件的发光效率,二者在决定OLED效率和稳定性方面起着至关重要的作用。三嗪基团具有强吸电性,电子亲和能高于大部分的杂环芳烃,可有效加深LUMO能级,利于电子由电极注入,进而提高发光效率,降低能耗;同时三嗪基团亦有望增大HOMO能级,使材料获得空穴阻挡能力。1,3,5-三嗪基团,兼具三嗪的强电子亲和能与大π骨架具有的好的热性能和高膜层质量,同时其2,4,6位点因易受到亲核试剂攻击而便于其衍生物的合成。
然而,在这一领域中,器件的工作寿命,特别是蓝光器件的工作寿命,仍然是一个悬而未决的问题。总体来看,有机电致发光器件的未来发展方向将是高效率、长寿命、低成本的白光器件和全彩色显示器件,但该技术的产业化进程仍面临许多关键问题。而且现有兼备电子传输和空穴阻挡能力且具有优异器件性能的材料较少,且大部分材料的电子传导速率远小于空穴传导速率,制备得到的器件的寿命和发光效率提升不明显,因此,设计与寻找一种稳定高效的化合物,作为有机电致发光新型材料以克服其在实际应用过程中出现的不足,是有机电致发光器件材料研究工作中的重点与今后的研发趋势。
发明内容
针对现有技术的不足,本发明的目的在于提供一种具有电子传输功能的材料及其应用,所述材料包含带有取代基的9-烷基-9-芳基(或含氮的杂芳基)芴基团和含氮六元环(三嗪、嘧啶),其HOMO能级在适度范围内,可有效调控功能层间的势垒,利于电子传输,使迁移率加快,可作为有机电致发光器件的电子传输层材料或空穴阻挡层材料,实现低驱动电压、高发光效率和长使用寿命特性。
为达到此发明目的,本发明采用以下技术方案:
一方面,本发明提供一种具有电子传输功能的材料,所述具有电子传输功能的材料具有化学式I所示结构:
化学式I中:
R独立选自甲基、乙基或异丙基;
Ar1、Ar2独立选自以下基团:
其中,R1为甲基,m可以为0、1或2的整数,*代表基团的连接位点;
Ar3独立选自苯基、联苯基、萘基、苯基萘基、吡啶基、苯基吡啶基、甲基取代的吡啶基或甲基取代的苯基吡啶基;
Ar4独立选自苯基、联苯基、吡啶基、苯基吡啶基、甲基取代吡啶基或甲基取代的苯基吡啶基;
L独立选自苯基、联苯基或三联苯基;
Z1-Z3独立表示C或N,且至少同时有2个为N。
进一步优选,Ar3独立选自苯基或联苯基;
进一步优选,Z1-Z3中有3个N;
优选地,所述具有电子传输功能的材料具有如下任一种结构:
进一步优选地,所述具有电子传输功能的材料具有如下任一种结构:
优选地,所述具有电子传输功能的材料具有选自如下化合物中的任意一种:
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本发明的具有电子传输功能的材料可通过所属领域的技术人员已知的合成方法制备。或者,优选以下反应流程来进行制备。
上述式中,R、L、Z1-Z3、Ar1-Ar4如上述化学式Ⅰ中所定义,Hal1、Hal2独立的选自氯、溴或碘。
特别地,对于没有公开过的复杂原料,采用经典的Suzuki偶联反应和锂化反应合成,并应用到本发明中。
具体制备方法:
步骤1具体包括以下过程:
将原料A(1.0eq)、原料B(1.0-2.0eq)和醋酸钾(2.0-3.0eq)加入到反应瓶中,随后加入1,4-二氧六环,换气三次,氮气保护下加入三(二亚苄基丙酮)二钯(0.02-0.15eq)和X-Phos(0.1-0.2eq),升温到110-120℃,并回流反应3-18h;利用薄层色谱法检测反应,反应结束后,稍降温度,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用二氯甲烷萃取水相;合并有机相后浓缩,利用二氯甲烷和石油醚(V:V=1:4-1:10)的混合溶液,通过柱色谱法纯化得到中间体1。
步骤2具体包括以下过程:
将中间体1(1.0eq)和原料C(1.0-1.3eq)加入到反应瓶中,随后加入甲苯、乙醇、水的混合溶液(V:V:V=3:1:1),换气三次,氮气保护下加入四(三苯基膦)钯(0.01-0.03eq)和碳酸钾(2.0-4.0eq)或醋酸钯(0.03-0.06eq)、X-Phos(0.1-0.02eq)和碳酸铯(2.0-4.0eq),升温到80℃-120℃,并回流反应4-20h;利用薄层色谱法检测反应,反应结束后,稍降温度,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用二氯甲烷萃取水相;合并有机相后浓缩,利用二氯甲烷和石油醚(V:V=1:6-1:20)的混合溶液,通过柱色谱法纯化得到化学式Ⅰ。
第二方面,本发明提供了一种有机电致发光器件,包括阳极、阴极以及设与所述阳极和所述阴极之间的有机物层,所述有机物层包括如上所述的具有电子传输功能的材料。
优选地,所述有机物层包括电子传输层,所述电子传输层包括如上所述的具有电子传输功能的材料。
优选地,所述有机物层包括空穴阻挡层,所述空穴阻挡层包括如上所述的具有电子传输功能的材料。
优选地,所述有机物层还包括空穴注入层、空穴传输层、电子阻挡层、发光辅助层、发光层或电子注入层中的一种或至少两种的组合。
本发明的有机发光器件的有机材料层可以形成为单层结构,但也可以形成为其中层和有两个或更多个有机材料层的多层结构。例如,本发明的有机发光器件可以具有包括空穴注入层、空穴传输层、电子阻挡层、发光辅助层、发光层、空穴阻挡层、电子传输层、电子注入层等作为有机材料层的结构。然而,有机发光器件的结构不限于此,并且可以包括更少数量的有机材料层或更多数量的有机材料层。
作为阳极材料,通常优选具有大功函数的材料使得空穴顺利注入有机材料层。在本发明中能够使用的阳极材料的具体实例包括:金属,例如钒、铬、铜、锌和金,或其合金;金属氧化物,例如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO);金属和氧化物的组合,例如ZnO:Al或SnO2:Sb;导电聚合物,例如聚(3-甲基噻吩)、聚[3,4-(乙烯-1,2-二氧)噻吩](PEDOT)、聚吡咯和聚苯胺,但不限于此。
空穴注入材料是有利地在低电压下接收来自阳极的空穴的材料,并且空穴注入材料的最高占据分子轨道(HOMO)优选地在阳极材料的功函数与周围有机材料层的HOMO之间。空穴注入材料的具体实例包括金属卟啉、低聚噻吩、基于芳基胺的有机材料、基于六腈六氮杂苯并菲的有机材料、基于喹吖啶酮的有机材料、基于苝的有机材料、蒽醌、以及基于聚苯胺和基于聚噻吩的导电聚合物等,但不限于此,并且还可以包含能够进行p掺杂的另外的化合物。
空穴传输材料是能够接收来自阳极或空穴注入层的空穴并将空穴传输至发光层的材料,并且具有高空穴迁移率的材料是合适的。其具体实例包括基于芳基胺的有机材料、导电聚合物、同时具有共轭部分和非共轭部分的嵌段共聚物等,但不限于此。
发光层可以发射红色、绿色或蓝色的光,并且可以由磷光材料或荧光材料形成。发光材料是能够通过接收分别来自空穴传输层和电子传输层的空穴和电子并使空穴与电子结合而发出在可见光区域内的光的材料,并且优选为对荧光或磷光具有有利的量子效率的材料。其具体实例包括:8-羟基喹啉铝配(Alq3);基于咔唑的化合物;二聚苯乙烯基化合物;BAlq;10-羟基苯并喹啉-金属化合物;基于苯并咔唑、基于苯并噻唑和基于苯并咪唑的化合物;基于聚(对亚苯基亚乙烯基)(PPV)的聚合物;螺环化合物;聚芴;红荧烯等,但不限于此。
发光层可以包含主体材料和掺杂材料。
发光层的主体材料包括稠合芳族环衍生物、含杂环的化合物等。具体地,稠合芳族环衍生物包括蒽衍生物、芘衍生物、萘衍生物、并五苯衍生物、菲化合物、荧蒽化合物等,含杂环的化合物包括咔唑衍生物、二苯并呋喃衍生物、梯子型呋喃化合物、嘧啶衍生物等,然而,材料不限于此。
发光层的掺杂材料包括荧光掺杂和磷光掺杂。可以选自芳香族胺衍生物、苯乙烯基胺化合物、硼配合物、荧蒽化合物、金属配合物等。
空穴阻挡层会将来自阳极的空穴阻挡在器件发光层的界面处,进而提高器件发光层界面处电子和空穴再结合的概率,增大器件的发光效率。本发明中化学式Ⅰ所示的化合物可作为空穴阻挡层。
电子传输层可以起到促进电子传输的作用。电子传输材料是有利地接收来自阴极的电子并将电子传输至发光层的材料,具有高电子迁移率的材料是合适的。本发明中化学式Ⅰ所示的化合物可作为电子传输层材料。
电子注入层可以起到促进电子注入的作用。电子注入材料优选为这样的化合物:其具有传输电子的能力,具有来自阴极的注入电子效应,对发光层或发光材料具有优异的电子注入效应,防止发光层中产生的激子迁移至空穴注入层,并且除此之外,具有优异的薄膜形成能力。其具体实例包括芴酮、蒽醌二甲烷、联苯醌、噻喃二氧化物、唑、二唑、三唑、咪唑、苝四羧酸、亚芴基甲烷、蒽酮等及其衍生物,金属配合物,含氮5元环衍生物等,但不限于此。
作为阴极材料,通常优选具有小功函数的材料使得电子顺利注入有机材料层。阴极材料的具体实例包括:金属,例如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅,或其合金;多层结构材料,例如LiF/Al或LiO2/Al;等等,但不限于此。
另一方面,本发明提供一种有机发光装置,所述有机发光装置包括如上所述的有机电致发光器件。
本发明所述有机发光装置,包括但不限于平板显示器、计算机监视器、、医用监护仪、电视机、广告牌、用于内部或外部照明和/或信号的灯、平视显示器、全透明或部分透明的显示器、柔性显示器、激光打印机、电话机、手机、片剂、相簿、个人数字助理(PDA)、可穿戴装置、笔记本电脑、数码相机、摄像机、取景器、微型显示器、三维显示器、虚拟现实或增强现实显示器、车辆、包括平铺在一起的多个显示器的视频墙、剧场或场馆屏幕、光疗装置和标志。
相对于现有技术,本发明具有如下有益效果:
本发明化合物有效呈现蓝色电子传输功能材料的特性,用其所制备的有机电致发光器件的驱动电压低,且使用寿命及效率明显提高。通过引入三嗪、嘧啶六元氮杂环来提升有机分子的迁移率,其中的N原子具有良好的电子传输性能,它们可拉低分子LUMO能级的能力,有利于与高功函的电极匹配,实现材料导电能力的增强,尤其是1,3,5-三嗪由于具有高电子亲和力、电化学稳定性及结构易修饰等优点。随后引入一个桥联的L基团(亚苯基、亚联苯基、亚三联苯基),可起缓冲作用,使得体系延长,电子流动性增强,从而提升器件的发光效率,而且也增大分子体积,减少分子聚集堆积,使整体构型更加扭曲,更利于后期器件的制作。再连接一个芴基团,可平衡整体分子的分子量,进而调控蒸镀温度,使其不至于过高,且在芴的9位其中一个取代基为烷基(甲基、乙基、异丙基),另一个取代基为芳基或含氮的杂芳基(苯基、联苯基、吡啶基、苯基吡啶基、甲基取代的吡啶基、甲基取代的苯基吡啶基),一方面可调整分子HOMO/LUMO能级,另一方面具有良好的化学稳定性,更有利于提升器件的寿命,同时芴的外侧连接一个取代基,可有限延长分子共轭体系,避免载流子迁移局域化,能够减低空穴传输能障,提升迁移速率,从而降低电压并提高器件的发光效率。
附图说明
图1是本发明实施例1制备的化合物1的核磁共振氢谱图。
具体实施方式
下面对本发明实施例中的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
另外,需要说明的是,以下实施例中所给出的数值是尽可能精确,但是本领域技术人员理解由于不可能避免的测量误差和实验操作问题,每一个数字都应该被理解为约数,而不是绝对准确的数值。
下列B-1、B-24和B-56是同一物质,且为现有技术,CAS号为73183-34-3。
实施例1
将原料A-1(1.0eq,CAS号:2842863-92-5)、原料B-1(1.5eq,CAS号:73183-34-3)和醋酸钾(2.0eq)加入到反应瓶中,随后加入1,4-二氧六环,换气三次,氮气保护下加入三(二亚苄基丙酮)二钯(0.02eq)和X-Phos(2-双环己基膦-2',4',6'-三异丙基联苯,0.1eq),升温到120℃,并回流反应8h;利用薄层色谱法检测反应,反应结束后,稍降温度,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用二氯甲烷萃取水相;合并有机相后浓缩,利用二氯甲烷和石油醚(V:V(体积比)=1:5)的混合溶液,通过柱色谱法纯化得到中间体1(产率:77.6%)。
将中间体1(1.0eq)和原料C-1(1.0eq,CAS号:1606981-69-4)加入到反应瓶中,随后加入甲苯、乙醇、水的混合溶液(V:V:V=3:1:1),换气三次,氮气保护下加入四(三苯基膦)钯(0.03eq)和碳酸钾(3.0eq),升温到95℃,并回流反应14h;利用薄层色谱法检测反应,反应结束后,稍降温度,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用二氯甲烷萃取水相;合并有机相后浓缩,利用二氯甲烷和石油醚(V:V=1:8)的混合溶液,通过柱色谱法纯化得到化合物1(产率:83.1%)。
对所得化合物1进行检测分析,结果如下:
HPLC纯度:>99.8%。
质谱测试:型号为Waters XEVO TQD的质谱仪,采用ESI源。
测试值MS(ESI,m/Z):[M+H]+=716.38。
元素分析:
计算值为:C,88.92;H,5.21;N,5.87;
测试值为:C,88.54;H,5.45;N,6.13。
化合物1的核磁共振氢谱图如图1所示。
实施例2
将原料A-24(1.0eq,CAS号:2356110-93-3、原料B-24(1.5eq,CAS号:73183-34-3)和醋酸钾(2.0eq)加入到反应瓶中,随后加入1,4-二氧六环,换气三次,氮气保护下加入三(二亚苄基丙酮)二钯(0.02eq)和X-Phos(0.1eq),升温到120℃,并回流反应10h;利用薄层色谱法检测反应,反应结束后,稍降温度,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用二氯甲烷萃取水相;合并有机相后浓缩,利用二氯甲烷和石油醚(V:V=1:5)的混合溶液,通过柱色谱法纯化得到中间体1(产率:75.5%)。
将中间体1(1.0eq)和原料C-24(1.0eq,CAS号:2758400-78-9)加入到反应瓶中,随后加入甲苯、乙醇、水的混合溶液(V:V:V=3:1:1),换气三次,氮气保护下加入四(三苯基膦)钯(0.03eq)和碳酸钾(3.0eq),升温到95℃,并回流反应16h;利用薄层色谱法检测反应,反应结束后,稍降温度,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用二氯甲烷萃取水相;合并有机相后浓缩,利用二氯甲烷和石油醚(V:V=1:10)的混合溶液,通过柱色谱法纯化得到化合物24(产率:79.8%)。
对所得化合物24进行检测分析,结果如下:
HPLC纯度:>99.8%。
质谱测试:型号为Waters XEVO TQD的质谱仪,采用ESI源。
测试值MS(ESI,m/Z):[M+H]+=817.33。
元素分析:
计算值为:C,88.21;H,4.94;N,6.86;
测试值为:C,87.82;H,5.17;N,7.13。
实施例3
将原料A-56(1.0eq,CAS号:2606032-01-1)、原料B-56(1.5eq,CAS号:73183-34-3)和醋酸钾(2.0eq)加入到反应瓶中,随后加入1,4-二氧六环,换气三次,氮气保护下加入三(二亚苄基丙酮)二钯(0.02eq)和X-Phos(0.1eq),升温到120℃,并回流反应10h;利用薄层色谱法检测反应,反应结束后,稍降温度,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用二氯甲烷萃取水相;合并有机相后浓缩,利用二氯甲烷和石油醚(V:V=1:6)的混合溶液,通过柱色谱法纯化得到中间体1(产率:72.3%)。
将中间体1(1.0eq)和原料C-56(1.0eq,CAS号:2583051-98-1)加入到反应瓶中,随后加入甲苯、乙醇、水的混合溶液(V:V:V=3:1:1),换气三次,氮气保护下加入四(三苯基膦)钯(0.03eq)和碳酸钾(3.0eq),升温到95℃,并回流反应14h;利用薄层色谱法检测反应,反应结束后,稍降温度,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用二氯甲烷萃取水相;合并有机相后浓缩,利用二氯甲烷和石油醚(V:V=1:9)的混合溶液,通过柱色谱法纯化得到化合物56(产率:81.2%)。
对所得化合物56进行检测分析,结果如下:
HPLC纯度:>99.7%。
质谱测试:型号为Waters XEVO TQD的质谱仪,采用ESI源。
测试值MS(ESI,m/Z):[M+H]+=805.42。
元素分析:
计算值为:C,88.03;H,5.01;N,6.96;
测试值为:C,87.66;H,5.27;N,7.18。
实施例4-85
参照实施例1至3的合成方法完成对如下化合物的合成,采用型号为Waters XEVOTQD的质谱仪进行测试,其精度低,用ESI源进行测试,其质谱测试值如下表1所示。
表1实施例4-85的质谱测试值
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另外,需要说明,本发明其他化合物参照上述所列举的实施例的合成方法即可获得,所以在此不再一一例举。
器件实施例1:有机电致发光器件制备
所制备OLED器件的结构为:ITO阳极/HIL/HTL/Prime/EML/HBL/ETL/EIL/阴极/光取出层。
a、ITO阳极:将涂层厚度为的ITO(氧化铟锡)-Ag-ITO(氧化铟锡)玻璃基板在蒸馏水中清洗2次,超声波洗涤30min,再用蒸馏水反复清洗2次,超声波洗涤10min,洗涤结束后,用甲醇、丙酮、异丙醇依次超声波洗涤(每次洗涤5min),干燥,然后转移至等离子体清洗机内洗涤5min,再送至蒸镀机中,以该基板为阳极,在其上依次蒸镀其它功能层。
b、HIL(空穴注入层):以的蒸镀速率,真空蒸镀空穴注入层材料HT和P-dopant。所述HT和P-dopant的蒸镀速率比为97:3,厚度为10nm。
c、HTL(空穴传输层):以的蒸镀速率,在空穴注入层上面真空蒸镀120nm的HT作为空穴传输层。
d、Prime(发光辅助层):以的蒸镀速率,在空穴传输层上面真空蒸镀5nm的Prime作为发光辅助层。
e、EML(发光层):然后在上述发光辅助层上,以的蒸镀速率,真空蒸镀厚度为25nm的主体材料(Host)和掺杂材料(Dopant)作为发光层。其中Host和Dopant的蒸镀速率比为98:2。
f、HBL(空穴阻挡层):以的蒸镀速率,真空蒸镀厚度为5.0nm的空穴阻挡层HB。
g、ETL(电子传输层):以的蒸镀速率,真空蒸镀厚度为30nm的化合物7和Liq作为电子传输层。其中化合物7和Liq的蒸镀速率比为50:50。
h、EIL(电子注入层):以的蒸镀速率,蒸镀Yb膜层1.0nm,形成电子注入层。
i、阴极:以的蒸镀速率比,蒸镀镁和银13nm,其蒸镀速率比为1:9,得到OLED器件。
j、光取出层:以的蒸镀速率,在阴极上真空蒸镀厚度为65nm的CPL,作为光取出层。
K、随后将蒸镀完成的基板进行封装。首先采用涂胶设备将清洗后盖板用UV胶进行涂覆工艺,然后将涂覆完成的盖板移至压合工段,将蒸镀完成的基板置于盖板上端,最后将基板和盖板在贴合设备作用下进行贴合,同时完成对UV胶光照固化。
如上所需材料结构如下所示:
参照上述器件实施例1提供的方法,分别选用表2中相对应的化合物替代化合物7,进行电子传输层的蒸镀,并制备得到相应的有机电致发光器件,分别记为器件实施例2~29。
器件对比例1-9:
该对比例提供了一种有机电致发光器件,该有机电致发光器件的制备方法与器件实施例1的唯一区别在于,该有机电致发光器件是采用现有的对比化合物a-i替代上述器件实施例1中的电子传输层(化合物7)进行蒸镀。其中,对比化合物a-i的化学结构式如下:
在1000(nits)亮度下对上述器件实施例1~29以及器件对比例1~9得到的有机电致发光器件的驱动电压、BI值以及寿命进行表征,测试结果如下表2:
表2器件测试结果
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器件实施例30:有机电致发光器件制备
所制备OLED器件的结构为:ITO阳极/HIL/HTL/Prime/EML/HBL/ETL/EIL/阴极/光取出层。
a、ITO阳极:将涂层厚度为的ITO(氧化铟锡)-Ag-ITO(氧化铟锡)玻璃基板在蒸馏水中清洗2次,超声波洗涤30min,再用蒸馏水反复清洗2次,超声波洗涤10min,洗涤结束后,用甲醇、丙酮、异丙醇依次超声波洗涤(每次洗涤5min),干燥,然后转移至等离子体清洗机内洗涤5min,再送至蒸镀机中,以该基板为阳极,在其上依次蒸镀其它功能层。
b、HIL(空穴注入层):以的蒸镀速率,真空蒸镀空穴注入层材料HT和P-dopant。所述HT和P-dopant的蒸镀速率比为97:3,厚度为10nm。
c、HTL(空穴传输层):以的蒸镀速率,在空穴注入层上面真空蒸镀120nm的HT作为空穴传输层。
d、Prime(发光辅助层):以的蒸镀速率,在空穴传输层上面真空蒸镀5nm的Prime作为发光辅助层。
e、EML(发光层):然后在上述发光辅助层上,以的蒸镀速率,真空蒸镀厚度为25nm的主体材料(Host)和掺杂材料(Dopant)作为发光层。其中Host和Dopant的蒸镀速率比为98:2。
f、HBL(空穴阻挡层):以的蒸镀速率,真空蒸镀厚度为5.0nm的化合物1。
g、ETL(电子传输层):以的蒸镀速率,真空蒸镀厚度为30nm的ET和Liq作为电子传输层。其中ET和Liq的蒸镀速率比为50:50。
h、EIL(电子注入层):以的蒸镀速率,蒸镀Yb膜层1.0nm,形成电子注入层。
i、阴极:以的蒸镀速率比,蒸镀镁和银13nm,其蒸镀速率比为1:9,得到OLED器件。
j、光取出层:以的蒸镀速率,在阴极上真空蒸镀厚度为65nm的CPL,作为光取出层。
K、随后将蒸镀完成的基板进行封装。首先采用涂胶设备将清洗后盖板用UV胶进行涂覆工艺,然后将涂覆完成的盖板移至压合工段,将蒸镀完成的基板置于盖板上端,最后将基板和盖板在贴合设备作用下进行贴合,同时完成对UV胶光照固化。
上述所需材料结构如下所示:
参照上述器件实施例30提供的方法,分别选用表3中相对应的化合物替代化合物1,进行电子传输层的蒸镀,并制备得到相应的有机电致发光器件,分别记为器件实施例31~85。
器件对比例10-16:
该对比例提供了一种有机电致发光器件,该有机电致发光器件的制备方法与器件实施例30的唯一区别在于,该有机电致发光器件是采用现有的对比化合物j-p替代上述器件实施例30中的空穴阻挡层(化合物1)进行蒸镀。其中,对比化合物j-p的化学结构式如下:
在1000(nits)亮度下对上述器件实施例30~85以及器件对比例10~16得到的有机电致发光器件的驱动电压、BI值以及寿命进行表征,测试结果如下表3:
表3器件测试结果
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本领域技术人员可知,在蓝光顶发射器件中,发光效率受色度影响较大,因此将色度对效率的影响因素考虑进去,将发光效率与CIEy比值定义为BI值,即BI=(cd/A)/CIEy。
从表2、表3的数据来看,使用本发明提供的材料制备的有机电致发光器件与对比化合物a-p所制备的器件相比,驱动电压,BI和寿命均得到提升。
化合物130、129和对比化合物a、b分别为平行对比例,其区别在于:对比化合物a、b中9-甲基-9-苯基芴内侧的苯环上含有取代基(苯基、吡啶基),而本发明化合物130、129中9-甲基-9-苯基芴上相同的取代基在外侧的苯环上,有效延长共轭体系至四个苯环(中间一个苯环、二苯并呋喃上的两个苯环和外侧取代基上的一个苯环),导致化合物的迁移率增加,从而降低电压并提高器件发光效率。
对比化合物d、e、f是本申请人在先研究的专利申请CN116655611A中的化合物,和化合物64、51、57分别为对比例,其区别在于:对比化合物d、e、f是芴的9号位上是甲基和二苯并呋喃基团,二苯并呋喃刚性强,蒸镀温度提高,稳定性下降,从而导致器件的寿命缩短,而本发明化合物64、51、57中芴的9号位上是甲基和芳基或含氮的杂芳基(苯基吡啶基、吡啶基、联苯基),扭转角小,结构整体稳定性更高,寿命更长,且芴的外侧有取代基可有效延长共轭体系,此外三嗪与芴之间带有桥联的L基团(亚苯基),通过亚苯基的缓冲使得体系延长,分子流动性增强,从而提升器件的发光效率。
对比化合物g、h、i是本申请人在先研究的专利申请CN116283909B中的化合物,和化合物131、101、73分别为对比例,其区别在于:化合物g、h、i中的L基团(亚萘基、亚萘基苯基、亚萘基)一端接三嗪,另一端连接芴的9号位上的苯环,而本发明化合物131、101、73中的L基团(亚苯基、亚联苯基、亚三联苯基)一端连接三嗪,另一端连接在芴下方的苯环上,且芴的外侧带有取代基,与对比化合物的共轭面(芴自身的两个苯环不参与共轭)相比,本发明化合物的共轭面不同,能隙窄,利于电子传输,迁移率更快,使得电压更低。
化合物1、136、53和对比化合物j、k、l分别为平行对比例,其区别在于:对比化合物j、k、l中的9甲基-9-苯基芴的外侧没有取代基,而本发明化合物1、136、53中的9甲基-9-苯基芴上有苯基取代,有效延长分子共轭体系,避免载流子迁移局域化,用于器件后,能够降低空穴传输能障,提升迁移速率,从而降低电压并提高器件发光效率。
化合物45和对比化合物p为平行对比例,其区别在于:对比化合物p中是9,9-二苯基芴,而本发明化合物45中是9-甲基-9-苯基芴,芴的9位上的两个苯基并没有起到延长共轭体系的作用,反而增加了分子量,使得蒸镀温度更高,造成材料不稳定,影响器件的寿命,而且两个苯基的存在增大了所在基团整体的空间位阻,影响化合物的迁移率。
申请人声明,本发明通过上述实施例来说明本发明的材料及其制备方法和应用,但本发明并不局限于上述实施例,即不意味着本发明必须依赖上述实施例才能实施。所属技术领域的技术人员应该明了,对本发明的任何改进,对本发明所选用原料的等效替换及辅助成分的添加、具体方式的选择等,均落在本发明的保护范围和公开范围之内。
Claims (10)
1.一种具有电子传输功能的材料,所述具有电子传输功能的材料具有化学式I所示结构:
化学式I中:
R独立选自甲基、乙基或异丙基;
Ar1、Ar2独立选自以下基团:
其中,R1为甲基,m可以为0、1或2的整数,*代表基团的连接位点;
Ar3独立选自苯基、联苯基、萘基、苯基萘基、吡啶基、苯基吡啶基、甲基取代的吡啶基或甲基取代的苯基吡啶基;
Ar4独立选自苯基、联苯基、吡啶基、苯基吡啶基、甲基取代吡啶基或甲基取代的苯基吡啶基;
L独立选自苯基、联苯基或三联苯基;
Z1-Z3独立表示C或N,且至少同时有2个为N。
2.根据权利要求1所述的具有电子传输功能的材料,其特征在于,Ar3独立选自苯基或联苯基;
进一步优选,Z1-Z3中有3个N。
3.根据权利要求1或2所述的具有电子传输功能的材料,其特征在于,所述具有电子传输功能的材料具有如下任一种结构:
4.根据权利要求1-3中任一项所述的具有电子传输功能的材料,其特征在于,所述具有电子传输功能的材料具有如下任一种结构:
5.根据权利要求1-4中任一项所述的具有电子传输功能的材料,其特征在于,所述具有电子传输功能的材料具有选自如下化合物中的任意一种:
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6.一种有机电致发光器件,其特征在于,包括阳极、阴极以及设与所述阳极和所述阴极之间的有机物层,所述有机物层包括如权利要求1-5中任一项所述的具有电子传输功能的材料。
7.根据权利要求6所述的有机电致发光器件,其特征在于,所述有机物层包括电子传输层,所述电子传输层包括如权利要求1-5中任一项所述的具有电子传输功能的材料。
8.根据权利要求6所述的有机电致发光器件,其特征在于,所述有机物层包括空穴阻挡层,所述空穴阻挡层包括如权利要求1-5中任一项所述的具有电子传输功能的材料。
9.根据权利要求6所述的有机电致发光器件,其特征在于,所述有机物层还包括空穴注入层、空穴传输层、电子阻挡层、发光辅助层、发光层或电子注入层中的一种或至少两种的组合。
10.一种有机发光装置,其特征在于,所述有机发光装置包括如权利要求6-9中任一项所述的有机电致发光器件。
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