CN114751888A - 一种电子传输材料及其制备方法、发光器件、发光装置 - Google Patents
一种电子传输材料及其制备方法、发光器件、发光装置 Download PDFInfo
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- CN114751888A CN114751888A CN202210663748.4A CN202210663748A CN114751888A CN 114751888 A CN114751888 A CN 114751888A CN 202210663748 A CN202210663748 A CN 202210663748A CN 114751888 A CN114751888 A CN 114751888A
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- electron transport
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- 125000001424 substituent group Chemical group 0.000 claims abstract description 19
- 125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 73
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
- -1 methoxy, cyano, fluoro, phenyl Chemical group 0.000 claims description 28
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- 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
本申请适用于材料技术领域,提供了一种电子传输材料及其制备方法、发光器件、发光装置。本申请以菲为母核,在9,10位仅存在一个特定取代基,且在2,3位与吸电子基团之间存在连接基团,将所得到的如通式I所示化合物作为电子传输材料,制备成的发光器件与现有技术相比,具有低驱动电压,高发光效率、BI和长寿命的性能优点;尤其在BI值上普遍提高5‑8%,在本领域已经实现了显著提高发光效率的技术效果。
Description
技术领域
本申请属于材料技术领域,尤其涉及一种电子传输材料及其制备方法、发光器件、发光装置。
背景技术
有机发光二极管(OLED:Organic Light Emitting Diode )作为一种新型和有前途的显示技术逐渐进入人们的视野。OLED是一种由多层有机薄膜结构形成的电致发光器件。有机电致发光元件是利用了如下原理的自发光元件:通过施加电场,利用由阳极注入的空穴与由阴极注入的电子的复合能使荧光性物质发光。
它具有如下结构:阳极、阴极以及介于两者之间的有机材料层。为了提高有机电致发光元件的效率和稳定性,有机材料层通常包括具有不同材料的多层,例如空穴注入层(HIL)、空穴传输层(HTL)、发光层、电子传输层(ETL)和电子注入层(EIL)。这种有机发光元件中,当在阳极和阴极之间施加电压时,来自阳极的空穴和来自阴极的电子注入有机材料层,产生的激子在迁移至基态时产生具有特定波长的光。
电子传输层是OLED结构中的一个关键组成部分,负责调节电子的注入速度和注入量,目前作为电子传输层所用到的电子传输型材料的结构中通常包含具有电子传输性能的吡啶、嘧啶、噁二唑、三氮唑、咪唑等含氮杂环等吸电子基团,但是一般有机材料的电子迁移率低,而空穴迁移率较高,使发光器件内部的电子-空穴不平衡,从而导致器件效率降低,稳定性差,寿命短等问题。
因此,研发一种具有高迁移率电子传输材料使其制备而成的有机电致发光器件具有低驱动电压,高效率,长寿命的性能优点是本领域人员亟需解决的技术问题。
发明内容
本申请的目的在于提供一种电子传输材料,旨在解决现有的发光器件效率降低,稳定性差,寿命短等问题。
本申请是这样实现的,一种电子传输材料,所述电子传输材料的结构通式如通式I所示:
所述L独立的选自取代或未经取代的C6-C18的芳基,取代或未经取代的C6-C24的杂芳基,杂原子为N、O、S;
所述Z1,Z2,Z3中至少有一个为N,其余为C;
所述Ar1,Ar2各自独立的选自取代或未经取代的C6-C18的芳基,取代或未经取代的C6-C24的杂芳基,杂原子为N、O、S;
所述n为1-5的整数;
条件1:X1-X5全部为碳原子,R至少存在一个强吸电子基团,R除强吸电子基团外,可以选自如下基团:氢,甲基,乙基,丙基,异丙基,苯基,甲基苯基,萘基,联苯基,三联苯基;
所述强吸电子基团为如下基团:
条件2:X1-X5中N原子个数为1-3,其余为C原子,R各自独立的选自氢,甲基,乙基,丙基,异丙基,甲氧基,氰基,氟基,苯基,氰基苯基,甲基苯基,萘基,联苯基,三联苯基以及如下所示取代基:
其中,所述R'各自独立的选甲基,乙基,甲氧基,氰基,苯基,吡啶基,嘧啶基,哒嗪基,吡嗪基。
本申请的另一目的在于一种电子传输材料的制备方法,包括:
N2保护下,将反应物A-I、反应物B-I、四(三苯基膦)钯和碳酸钾分别加入到甲苯、乙醇、水的混合溶剂中,升温至85-100℃,反应8-12h,得到中间体C-I;
N2保护下,将所述中间体C-I、反应物D-I、醋酸钯和2-环己基-2,4,6-三异丙基联苯、碳酸铯分别加入到甲苯、乙醇、水的混合溶剂中,升温至80-100℃,反应8-12h,得到通式I所示的电子传输材料。
本申请的另一目的在于一种发光器件,所述发光器件包括所述的电子传输材料或者所述的电子传输材料的制备方法制备的电子传输材料。
本申请的另一目的在于一种发光装置,所述发光装置包括所述的发光器件。
本申请提供的电子传输材料,以菲为母核,在9,10位仅存在一个特定取代基,且在2,3位与吸电子基团(三嗪,吡啶,嘧啶)之间存在连接基团,通过该电子传输材料制备成的发光器件与现有技术相比,具有低驱动电压,高发光效率、BI和长寿命的性能优点。尤其在BI值上普遍提高5-8%,在本领域已经实现了显著提高发光效率的技术效果。
具体地,三嗪,吡啶,嘧啶是吸电子能力强的官能团,通过基团与菲的2,3位连接,能够有效提高电子传输材料的电子迁移率。改善有机电致发光器件内部电子-空穴不平衡的问题,提高发光效率。并且,用含有吡啶,苯,嘧啶的一系列特定取代基团在菲的9或10位取代,进一步提高电子传输材料的电子迁移率的同时,平面分子结构能使核心结构的π-共轭体系不被延续,保证高三线态能级(ET),宽带隙。进一步提高发光效率,并改善器件各层能级匹配程度,降低驱动电压,延长器件寿命。
附图说明
图1是本申请实施例提供的化合物1的核磁共振氢谱图;
图2是本申请实施例提供的化合物453的核磁共振氢谱图。
具体实施方式
为了使本申请的目的、技术方案及优点更加清楚明白,以下结合附图及实施例,对本申请进行进一步详细说明。应当理解,此处所描述的具体实施例仅仅用以解释本申请,并不用于限定本申请。
本申请提供了一种电子传输材料,其结构如下所示:
其中,L各自独立的选自取代或未经取代的C6-C18的芳基,取代或未经取代的C6-C24的杂芳基,杂原子可以为N、O、S;
优选,L各自独立的选自苯基,萘基,菲基,甲基苯基,苯基萘基,氰基苯基,苯基吡啶基,联苯基,三联苯基,三嗪基,二苯并呋喃基,二苯并噻吩基,芴基,吡啶基,嘧啶基,喹啉基,喹喔啉基;
Z1,Z2,Z3中至少有一个N,其余为C;
Ar1,Ar2各自独立的选自取代或未经取代的C6-C18的芳基,取代或未经取代的C6-C24的杂芳基,杂原子可以为N、O、S;
n为1-5的整数;
1、X1-X5全部为碳原子,R至少存在一个强吸电子基团,R除强吸电子基团外,可以选自如下基团:氢,甲基,乙基,丙基,异丙基,苯基,甲基苯基,萘基,联苯基,三联苯基;
所述强吸电子基团为如下基团:
其中,R'各自独立的选甲基,乙基,甲氧基,氰基,苯基,吡啶基,嘧啶基,哒嗪基,吡嗪基;
2、X1-X5中N原子个数为1-3,其余为C原子,R各自独立的选自氢,甲基,乙基,丙基,异丙基,甲氧基,氰基,氟基,苯基,氰基苯基,甲基苯基,萘基,联苯基,三联苯基以及如下所示取代基:
其中,R'各自独立的选甲基,乙基,甲氧基,氰基,苯基,吡啶基,嘧啶基,哒嗪基,吡嗪基;
进一步,通式I具有如下所示通式:
更进一步,Z1-Z3全部为N;
更进一步,L连接位置优选为2,3位;
更进一步,L各自独立的选为苯基,萘基,联苯基,吡啶基,氰基苯基,苯基吡啶基,嘧啶基;
更进一步,Ar1,Ar2各自独立的选自苯基,甲基苯基,乙基苯基,氰基苯基,甲氧基苯基,苯基吡啶基,苯基嘧啶基,联苯基、三联苯基,萘基,二苯并呋喃基,咔唑基,二甲基芴基;
在上述技术方案中,术语“经取代或未经取代的”意指被选自以下的一个、两个或更多个取代基取代:氘;卤素基团;腈基;羟基;羰基;酯基;甲硅烷基;硼基;经取代或未经取代的烷基;经取代或未经取代的环烷基;经取代或未经取代的烷氧基;经取代或未经取代的烯基;经取代或未经取代的烷基胺基;经取代或未经取代的杂环基胺基;经取代或未经取代的芳基胺基;经取代或未经取代的芳基;和经取代或未经取代的杂环基,或者被以上所示的取代基中的两个或更多个取代基相连接的取代基取代,或者不具有取代基。例如,“两个或更多个取代基相连接的取代基”可以包括联苯基。换言之,联苯基可以为芳基,或者可以解释为两个苯基相连接的取代基。
本申请中,菲取代位置定义如下:
所述电子传输材料具体具有如下结构,但不仅限于此:
本申请还提供了上述的电子传输材料的制备方法,合成路线如下所示:
步骤1:
N2保护下,将反应物A-I(1.0eq)、反应物B-I(1-1.2eq)、Pd(PPh3)4(四(三苯基膦)钯)(0.01-0.02eq)和K2CO3(碳酸钾)(2.0-2.4eq)分别加入到甲苯、乙醇、水(2-4:1:1)的混合溶剂中,升温至85-100℃,反应8-12h,使用硅藻土趁热抽滤,除去盐和催化剂,滤液冷却至室温后,使用旋转式蒸发器去除溶剂,得到的固体干燥后过硅胶漏斗,以二氯甲烷:石油醚体积比为1:(3-6)作为展开剂,滤液用旋转式蒸发器去除,得到的固体干燥,得到中间体C-I。
步骤2:
N2保护下,将中间体C-I(1.0eq)、反应物D-I(1-1.2eq)、醋酸钯(Pd(OAc)2)(0.01-0.02eq)和2-环己基-2,4,6-三异丙基联苯(X-Phos)(0.1-0.2eq)碳酸铯(2.0-2.3eq)分别加入到甲苯、乙醇、水(2-4:1:1)的混合溶剂中,升温至80-100℃,反应8-12h,冷却至室温,加入H2O,待固体析出完毕后过滤,将滤饼烘干,得到的固体用甲苯加热溶解,趁热过硅胶漏斗,用甲醇:二氯甲烷体积比为1:(40-60)作为展开剂,将得到的旋转式蒸发器去除溶剂,得到的固体干燥,得到通式I。
下面将结合本申请的电子传输材料,对本申请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申请一部分实施例,而不是全部的实施例。
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。
实施例1 化合物1的合成
步骤1:
N2保护下,将反应物A-1(50mmol)、反应物B-1(60mmol)、四(三苯基膦)钯(0.5mmol)和碳酸钾(110mmol)分别加入到甲苯、乙醇、水(150mL:50mL:50mL)的混合溶剂中,升温至95℃,反应10h,使用硅藻土趁热抽滤,除去盐和催化剂,滤液冷却至室温后,使用旋转式蒸发器去除溶剂,得到的固体干燥后过硅胶漏斗,以二氯甲烷:石油醚体积比为1:6作为展开剂,滤液用旋转式蒸发器去除,得到的固体干燥,得到中间体C-1(13.99g,产率:88%,Mw:318.06)。
步骤2:
N2保护下,将中间体C-1(38mmol)、反应物D-1(45.6mmol)、醋酸钯(Pd(OAc)2)(0.38mmol)和2-环己基-2,4,6-三异丙基联苯(X-Phos)(0.38mmol)碳酸铯(83.6mmol)分别加入到甲苯、乙醇、水(114mL:38mL:38mL)的混合溶剂中,升温至90℃,反应8h,冷却至室温,加入H2O,待固体析出完毕后过滤,将滤饼烘干,得到的固体用甲苯加热溶解,趁热过硅胶漏斗,用甲醇:二氯甲烷体积比为1:60作为展开剂,将得到的旋转式蒸发器去除溶剂,得到的固体干燥,得到化合物1(17.30g,产率:77%)。
表征:
HPLC纯度:>99.7%。
质谱测试:理论值为590.73;测试值为591.38。
元素分析:
理论值:C, 85.40; H, 5.12; N, 9.48
测试值:C, 85.23; H, 5.30; N, 9.62。
核磁共振氢谱:如图1所示。
实施例2:化合物93的合成
步骤1:
N2保护下,将反应物A-93(50mmol)、反应物B-93(60mmol)、四(三苯基膦)钯(0.5mmol)和碳酸钾(110mmol)分别加入到甲苯、乙醇、水(150mL:50mL:50mL)的混合溶剂中,升温至95℃,反应9h,使用硅藻土趁热抽滤,除去盐和催化剂,滤液冷却至室温后,使用旋转式蒸发器去除溶剂,得到的固体干燥后过硅胶漏斗,以二氯甲烷:石油醚体积比为1:6作为展开剂,滤液用旋转式蒸发器去除,得到的固体干燥,得到中间体C-93(16.62g,产率:85%,Mw: 391.05)。
步骤2:
N2保护下,将中间体C-93(38mmol)、反应物D-93(45.6mmol)、醋酸钯(Pd(OAc)2)(0.38mmol)和2-环己基-2,4,6-三异丙基联苯(X-Phos)(0.38mmol)碳酸铯(83.6mmol)分别加入到甲苯、乙醇、水(114mL:38mL:38mL)的混合溶剂中,升温至90℃,反应8h,冷却至室温,加入H2O,待固体析出完毕后过滤,将滤饼烘干,得到的固体用甲苯加热溶解,趁热过硅胶漏斗,用甲醇:二氯甲烷体积比为1:50作为展开剂,将得到的旋转式蒸发器去除溶剂,得到的固体干燥,得到化合物93(18.93g,产率:75%)。
表征:
HPLC纯度:>99.8%。
质谱测试:理论值为663.78;测试值为664.38。
元素分析:
理论值:C, 85.05; H, 4.40; N, 10.55
测试值:C, 84.78; H, 4.61; N, 10.71
实施例3:化合物127的合成
步骤1:
N2保护下,将反应物A-127(50mmol)、反应物B-127(60mmol)、四(三苯基膦)钯(0.5mmol)和碳酸钾(105mmol)分别加入到甲苯、乙醇、水(150mL:50mL:50mL)的混合溶剂中,升温至90℃,反应10h,使用硅藻土趁热抽滤,除去盐和催化剂,滤液冷却至室温后,使用旋转式蒸发器去除溶剂,得到的固体干燥后过硅胶漏斗,以二氯甲烷:石油醚体积比为1:5作为展开剂,滤液用旋转式蒸发器去除,得到的固体干燥,得到中间体C-127(19.02g,产率:86%,Mw:442.31)。
步骤2:
N2保护下,将中间体C-127(38mmol)、反应物D-127(45.6mmol)、醋酸钯(Pd(OAc)2)(0.38mmol)和2-环己基-2,4,6-三异丙基联苯(X-Phos)(0.38mmol)碳酸铯(83.6mmol)分别加入到甲苯、乙醇、水(2-4:1:1)的混合溶剂中,升温至85℃,反应12h,冷却至室温,加入H2O,待固体析出完毕后过滤,将滤饼烘干,得到的固体用甲苯加热溶解,趁热过硅胶漏斗,用甲醇:二氯甲烷体积比为1:50作为展开剂,将得到的旋转式蒸发器去除溶剂,得到的固体干燥,得到化合物127(20.69g,产率:76%)。
表征:
HPLC纯度:>99.7%。
质谱测试:理论值为715.86;测试值为716.44。
元素分析:
理论值:C, 85.57; H, 4.65; N, 9.78
测试值:C, 85.39; H, 4.79; N, 9.94
实施例4:化合物453的合成
步骤1:
N2保护下,将反应物A-453(50mmol)、反应物B-453(60mmol)、四(三苯基膦)钯(0.5mmol)和碳酸钾(110mmol)分别加入到甲苯、乙醇、水(150mL:50mL:50mL)的混合溶剂中,升温至95℃,反应10h,使用硅藻土趁热抽滤,除去盐和催化剂,滤液冷却至室温后,使用旋转式蒸发器去除溶剂,得到的固体干燥后过硅胶漏斗,以二氯甲烷:石油醚体积比为1:4作为展开剂,滤液用旋转式蒸发器去除,得到的固体干燥,得到中间体C-453(13.18g,产率:84%,Mw:313.96)。
步骤2:
N2保护下,将中间体C-453(38mmol)、反应物D-453(45.6mmol)、醋酸钯(Pd(OAc)2)(0.38mmol)和2-环己基-2,4,6-三异丙基联苯(X-Phos)(0.38mmol)碳酸铯(83.6mmol)分别加入到甲苯、乙醇、水(114mL:38mL:38mL)的混合溶剂中,升温至90℃,反应8h,冷却至室温,加入H2O,待固体析出完毕后过滤,将滤饼烘干,得到的固体用甲苯加热溶解,趁热过硅胶漏斗,用甲醇:二氯甲烷体积比为1:50作为展开剂,将得到的旋转式蒸发器去除溶剂,得到的固体干燥,得到化合物453(16.07g,产率:72%)。
表征:
HPLC纯度:>99.8%。
质谱测试:理论值为586.70;测试值为587.4。
元素分析:
理论值:C, 85.98; H, 4.47; N, 9.55
测试值:C, 85.66; H, 4.66; N, 9.78。
核磁共振氢谱:如图2所示。
实施例5:化合物598的合成
步骤1:
N2保护下,将反应物A-598(50mmol)、反应物B-598(60mmol)、四(三苯基膦)钯(0.5mmol)和碳酸钾(110mmol)分别加入到甲苯、乙醇、水(150mL:50mL:50mL)的混合溶剂中,升温至90℃,反应10h,使用硅藻土趁热抽滤,除去盐和催化剂,滤液冷却至室温后,使用旋转式蒸发器去除溶剂,得到的固体干燥后过硅胶漏斗,以二氯甲烷:石油醚体积比为1:6作为展开剂,滤液用旋转式蒸发器去除,得到的固体干燥,得到中间体C-598(15.97g,产率:87%,Mw: 367.07)。
步骤2:
N2保护下,将中间体C-598(38mmol)、反应物D-598(45.6mmol)、醋酸钯(Pd(OAc)2)(0.38mmol)和2-环己基-2,4,6-三异丙基联苯(X-Phos)(0.38mmol)碳酸铯(83.6mmol)分别加入到甲苯、乙醇、水(114mL:38mL:38mL)的混合溶剂中,升温至90℃,反应8h,冷却至室温,加入H2O,待固体析出完毕后过滤,将滤饼烘干,得到的固体用甲苯加热溶解,趁热过硅胶漏斗,用甲醇:二氯甲烷体积比为1:50作为展开剂,将得到的旋转式蒸发器去除溶剂,得到的固体干燥,得到化合物598(18.40g,产率:74%)。
表征:
HPLC纯度:>99.8%。
质谱测试:理论值为653.79;测试值为654.41。
元素分析:
理论值:C, 84.51; H, 4.78; N, 10.71
测试值:C, 84.26; H, 4.91; N, 10.94
实施例6:化合物637的合成
步骤1:
N2保护下,将反应物A-637(50mmol)、反应物B-637(60mmol)、四(三苯基膦)钯(0.5mmol)和碳酸钾(110mmol)分别加入到甲苯、乙醇、水(150mL:50mL:50mL)的混合溶剂中,升温至90℃,反应8h,使用硅藻土趁热抽滤,除去盐和催化剂,滤液冷却至室温后,使用旋转式蒸发器去除溶剂,得到的固体干燥后过硅胶漏斗,以二氯甲烷:石油醚体积比为1:6作为展开剂,滤液用旋转式蒸发器去除,得到的固体干燥,得到中间体C-637(19.86g,产率:85%,Mw:467.22)。
步骤2:
N2保护下,将中间体C-637(38mmol)、反应物D-637(45.6mmol)、醋酸钯(Pd(OAc)2)(0.38mmol)和2-环己基-2,4,6-三异丙基联苯(X-Phos)(0.38mmol)碳酸铯(83.6mmol)分别加入到甲苯、乙醇、水(114mL:38mL:38mL)的混合溶剂中,升温至90℃,反应8h,冷却至室温,加入H2O,待固体析出完毕后过滤,将滤饼烘干,得到的固体用甲苯加热溶解,趁热过硅胶漏斗,用甲醇:二氯甲烷体积比为1:50作为展开剂,将得到的旋转式蒸发器去除溶剂,得到的固体干燥,得到化合物637(20.54g,产率:73%)。
表征:
HPLC纯度:>99.7%。
质谱测试:理论值为739.88;测试值为740.49。
元素分析:
理论值:C, 86.04; H, 4.50; N, 9.47
测试值:C, 85.71; H, 4.71; N, 9.69。
实施例7-123
参照实施例1至6的合成方法完成对如下化合物的合成,其分子式和质谱如下表1所示:
另外,需要说明,本申请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。
本申请提供了一种发光器件,可以具有包含空穴注入层、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、盖帽层等作为有机物层的结构。但是,发光器件的结构并不限于此,可以包含数量更少或更多的有机层。
根据本申请说明书的一个实施方式,上述有机物层具有电子传输层,本申请制备的通式I所示化合物作为电子传输层材料。
关于上述通式I所表示的化合物,在制造发光器件时,可以利用真空蒸镀法,也可以利用溶液涂布法来形成有机物层。其中,所谓溶液涂布法是指,旋涂法、浸涂法、刮涂法、喷墨印刷法、丝网印刷法、喷雾法、辊涂法等,但并非仅限于此。
本申请的发光器件根据所使用的材料,可以为顶部发光型、底部发光型或双向发光型。
本申请所述的器件可以用于有机发光器件、有机太阳电池、电子纸、有机感光体或有机薄膜晶体管。
作为阳极物质,通常为了使空穴能够顺利地向有机物层注入,优选为功函数大的物质。作为本申请中可使用的阳极物质的具体例,有钒、铬、铜、锌、金等金属或它们的合金;氧化锌、氧化铟、氧化铟锡(ITO)、氧化铟锌(IZO)等金属氧化物;ZnO:A1或SnO2:Sb等金属与氧化物的组合;聚吡咯及聚苯胺等导电性高分子等。
空穴注入层优选为p掺杂的空穴注入层,p掺杂的空穴注入层意指掺杂有p掺杂剂的空穴注入层。p掺杂剂是能够赋予p型半导体特性的材料。p型半导体特性意指在HOMO能级下注入空穴或传输空穴的特性,即具有高空穴传导率的材料的特性。
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。空穴传输材料,可以选自芳基胺系衍生物、导电性高分子、以及同时存在共轭部分和非共轭部分的嵌段共聚物等。
空穴输送层和发光层之间加入发光辅助层(多层空穴输送层)。发光辅助层主要起到辅助空穴传输层的作用,因此有时也称为第二空穴传输层。发光辅助层使得从阳极转移的空穴能够平稳地移动到发光层,并且可以阻挡从阴极转移的电子,以将电子限制在发光层内,减少空穴传输层与发光层之间的势垒,降低有机电致发光器件的驱动电压,进一步增加空穴的利用率,从而改善器件的发光效率和寿命。
发光层的发光物质,是能够分别接收来自空穴传输层和电子传输层的空穴和电子并使其结合而发出可见光区域的光的物质,优选为对于荧光或磷光的量子效率高的物质。
发光层可以包含主体材料和掺杂剂材料。
主体材料和掺杂材料的质量比为90-99.5:0.5-10。
主体材料有芳香族稠环衍生物或含杂环化合物等。具体而言,作为芳香族稠环衍生物,有蒽衍生物、芘衍生物、萘衍生物、并五苯衍生物、菲化合物、荧蒽化合物等,作为含杂环化合物,有咔唑衍生物、二苯并呋喃衍生物、嘧啶衍生物等。
本申请掺杂剂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。
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,优选具有高电子迁移率的材料。电子传输层可以包括电子缓冲层、空穴阻挡层、电子传输层和电子注入层中的至少一个,并且优选电子传输层和电子注入层中的至少一个。本申请电子传输层材料为通式I所示化合物。
电子注入层可以起到促进电子注入的作用。具有传输电子的能力,防止发光层中产生的激子迁移至空穴注入层。电子注入层的材料包括噁唑、噁二唑、***、咪唑、苝四羧酸、亚芴基甲烷、蒽酮以及它们的衍生物、镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡、镱等金属或它们的合金,金属配合物或含氮5元环衍生物等,但并不限于此。
阴极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,该层的层厚度优选在0.5和5nm之间。阴极物质,通常为了使电子容易地向有机物层注入,优选为功函数小的物质。作为阴极物质的具体例,有镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡及铅等金属或它们的合金:LiF/A1或LiO2/A1,Mg/Ag等多层结构物质等。
除本申请所公开的电子传输层中包含通式I,OLED器件中对于其他层材料并无特殊限制。可以使用现有的空穴注入材料、空穴输送材料、空穴传输辅助材料,掺杂剂材料、空穴阻挡层材料、电子传输层材料和电子注入材料。
以下结合具体实施例对本申请提供的一种有机电致发光组合物和有机电致发光器件进行具体说明。
应用例1]有机电致发光器件制备:
a、ITO阳极:将涂层厚度为150nm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,然后转移至等甩干机内进行甩干,最后用真空烘箱220℃烘烤2小时,烘烤结束后降温即可使用。以该基板为阳极,使用蒸镀机进行蒸镀器件工艺,在其上依次蒸镀其它功能层。
b、HIL(空穴注入层):以1Å/s的蒸镀速率,真空蒸镀空穴注入层材料HT和P-dopant,其化学式如下所示。所述HT和P-dopant的蒸镀速率比为98:2,厚度为10nm;
c、HTL(空穴传输层):以1.5Å/s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0.5Å/s的蒸镀速率,在空穴传输层上面真空蒸镀10nm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1Å/s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Host和Dopant的化学式如下所示。其中Host和Dopant的蒸镀速率比为97:3。
f、HB(空穴阻挡层):以0.5Å/s的蒸镀速率,真空蒸镀厚度为5.0nm的空穴阻挡层。
g、ETL(电子传输层):以1Å/s的蒸镀速率,真空蒸镀厚度为35nm的化合物1和Liq作为电子传输层。其中化合物1和Liq的蒸镀速率比为50:50。
h、EIL(电子注入层):以0.5Å/s的蒸镀速率,蒸镀Yb膜层1.0nm,形成电子注入层。
i、阴极:以1Å/s的蒸镀速率比,蒸镀镁和银18nm,其蒸镀速率比为1:9,得到OLED器件。
j、光取出层:以1Å/s的蒸镀速率,在阴极上真空蒸镀厚度为70nm的CPL,作为光取出层。
k、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。
器件结构:
ITO/Ag/ITO/HT:P-dopant(10nm,2%)/HT(120nm)/prime (10nm)/Host: Dopant(25nm,3%)/HB(5nm)/ET:Liq(35nm,50%)/Yb(1nm)/Mg:Ag(18nm,1:9)/CPL(70nm)。
应用例2-123
按照上述有机电致发光器件的制备方法制备应用例2-123的有机电致发光器件,区别在于将应用例1中的化合物1分别替换为对应的化合物,形成电子传输层。
对比例1
按照上述有机电致发光器件的制备方法制备有机电致发光器件,区别在于将应用例1中的化合物1替换为对比化合物1,其中对比化合物1的结构式如下:
对比例2
按照上述有机电致发光器件的制备方法制备有机电致发光器件,区别在于将应用例1中的化合物1替换为对比化合物2,其中对比化合物2的结构式如下:
对比例3
按照上述有机电致发光器件的制备方法制备有机电致发光器件,区别在于将应用例1中的化合物1替换为对比化合物3,其中对比化合物3的结构式如下:
对比例4
按照上述有机电致发光器件的制备方法制备有机电致发光器件,区别在于将应用例1中的化合物1替换为对比化合物4,其中对比化合物4的结构式如下:
对比例5
按照上述有机电致发光器件的制备方法制备有机电致发光器件,区别在于将应用例1中的化合物1替换为对比化合物5,其中对比化合物5的结构式如下:
对比例6
按照上述有机电致发光器件的制备方法制备有机电致发光器件,区别在于将应用例1中的化合物1替换为对比化合物6,其中对比化合物6的结构式如下:
对比例7
按照上述有机电致发光器件的制备方法制备有机电致发光器件,区别在于将应用例1中的化合物1替换为对比化合物7,其中对比化合物7的结构式如下:
对比例8
按照上述有机电致发光器件的制备方法制备有机电致发光器件,区别在于将应用例1中的化合物1替换为对比化合物8,其中对比化合物8的结构式如下:
对比例9
按照上述有机电致发光器件的制备方法制备有机电致发光器件,区别在于将应用例1中的化合物1替换为对比化合物9,其中对比化合物9的结构式如下:
对比例10
按照上述有机电致发光器件的制备方法制备有机电致发光器件,区别在于将应用例1中的化合物1替换为对比化合物10,其中对比化合物10的结构式如下:
对比例11
按照上述有机电致发光器件的制备方法制备有机电致发光器件,区别在于将应用例1中的化合物1替换为对比化合物11,其中对比化合物11的结构式如下:
对比例12
按照上述有机电致发光器件的制备方法制备有机电致发光器件,区别在于将应用例1中的化合物1替换为对比化合物12,其中对比化合物12的结构式如下:
在1000(nits)亮度下对上述器件实施例1-123以及器件对比例1-12得到的有机电致发光器件的驱动电压、发光效率、BI值以及寿命进行表征,测试结果如下表2:
从表2可以看出,使用本申请提供的电子传输材料制备的有机电致发光器件应用例1~123与对比例1~12提供的现有的有机电致发光器件相比较而言,在驱动电压,发光效率、BI和寿命得到提高。
其中,对比化合物1与化合物5,对比化合物6与化合物453,569,对比化合物与本申请化合物的差别在于菲上9,10位的取代和取代基数目不同,本申请化合物5,453,569在BI,寿命上取得了大幅度提高;
对比化合物3与化合物606的差别在于菲上三嗪的取代位置不同,化合物606在BI,寿命,驱动电压上取得了大幅度提高;
对比化合物7菲上9位的取代基仅为苯,本申请化合物346则在相应位置为苯环上进一步修饰,对比化合物11与化合物524的差别在于在2,3位与吸电子基团三嗪之间存在连接基团,在BI,寿命,驱动电压上取得了大幅度提高。
除此之外,对比化合物8与化合物616是平行对比,对比化合物9与化合物608是平行对比,对比化合物10与化合物146是平行对比,菲上母核不同,取代位置不同,本申请化合物在性能上均取得了显著提升。
器件性能结果通过研究发现,本申请范围内的取代基在9位的发光效率提高非常显著,本申请范围内的取代基在10位的寿命提高非常明显,我司会在此基础上进一步开发符合产线需求的有机电致发光材料。
本申请的化合物满足以菲为母核,在9,10位仅存在一个本申请范围内的特定取代基,且在2,3位与吸电子基团(三嗪,吡啶,嘧啶)之间存在连接基团,通式I所示化合物作为电子传输材料,制备成的有机电致发光器件与现有技术相比,具有低驱动电压,高发光效率、BI和长寿命的性能优点。尤其在BI值上普遍提高5-8%,在本领域已经实现了显著提高发光效率的技术效果。
具体地,三嗪,吡啶,嘧啶是吸电子能力强的官能团,通过基团与菲的2,3位连接,能够有效提高电子传输材料的电子迁移率。改善有机电致发光器件内部电子-空穴不平衡的问题,提高发光效率。并且,用含有吡啶,苯,嘧啶的一系列特定取代基团在菲的9或10位取代,进一步提高电子传输材料的电子迁移率的同时,平面分子结构能使核心结构的π-共轭体系不被延续,保证高三线态能级(ET),宽带隙。进一步提高发光效率,并改善器件各层能级匹配程度,降低驱动电压,延长器件寿命。得到的本申请的化合物与现有技术相比具有优异的器件性能。
本说明书中各个实施例采用递进的方式描述,每个实施例重点说明的都是与其他实施例的不同之处,各个实施例之间相同相似部分互相参见即可。对于实施例公开的装置而言,由于其与实施例公开的方法相对应,所以描述的比较简单,相关之处参见方法部分说明即可。
对所公开的实施例的上述说明,使本领域专业技术人员能够实现或使用本申请。对这些实施例的多种修改对本领域的专业技术人员来说将是显而易见的,本文中所定义的一般原理可以在不脱离本申请的精神或范围的情况下,在其它实施例中实现。因此,本申请将不会被限制于本文所示的这些实施例,而是要符合与本文所公开的原理和新颖特点相一致的最宽的范围。
Claims (10)
1.一种电子传输材料,其特征在于,所述电子传输材料的结构通式如通式I所示:
所述L独立的选自取代或未经取代的C6-C18的芳基,取代或未经取代的C6-C24的杂芳基,杂原子为N、O、S;
所述Z1,Z2,Z3中至少有一个为N,其余为C;
所述Ar1,Ar2各自独立的选自取代或未经取代的C6-C18的芳基,取代或未经取代的C6-C24的杂芳基,杂原子为N、O、S;
所述n为1-5的整数;
条件1:X1-X5全部为碳原子,R至少存在一个强吸电子基团,R除强吸电子基团外,可以选自如下基团:氢、甲基、乙基、丙基、异丙基、苯基、甲基苯基、萘基、联苯基、三联苯基中的一种;
所述强吸电子基团为如下基团:
条件2:X1-X5中N原子个数为1-3,其余为C原子,R各自独立的选自氢、甲基、乙基、丙基、异丙基、甲氧基、氰基、氟基、苯基、氰基苯基、甲基苯基、萘基、联苯基、三联苯基以及如下所示的取代基之一:
其中,所述R'各自独立的选自甲基、乙基、甲氧基、氰基、苯基、吡啶基、嘧啶基、哒嗪基、吡嗪基中的一种。
3.根据权利要求1或2所述的电子传输材料,其特征在于,所述L独立的选自苯基,萘基,菲基,甲基苯基,苯基萘基,氰基苯基,苯基吡啶基,联苯基,三联苯基,三嗪基,二苯并呋喃基,二苯并噻吩基,芴基,吡啶基,嘧啶基,喹啉基,喹喔啉基。
4.根据权利要求1或2所述的电子传输材料,其特征在于,所述n为1-3的整数;所述Z1-Z3全部为N。
6.根据权利要求1或2所述的电子传输材料,其特征在于,所述L独立的选自苯基、萘基、联苯基、吡啶基、氰基苯基、苯基吡啶基、嘧啶基中的一种。
7.根据权利要求1或2所述的电子传输材料,其特征在于,所述Ar1,Ar2各自独立的选自苯基、甲基苯基、乙基苯基、氰基苯基、甲氧基苯基、苯基吡啶基、苯基嘧啶基、联苯基、三联苯基、萘基、二苯并呋喃基、咔唑基、二甲基芴基中的一种。
9.一种发光器件,其特征在于,所述发光器件包括权利要求1-7任一所述的电子传输材料或者根据权利要求8所述的电子传输材料的制备方法制备的电子传输材料。
10.一种发光装置,其特征在于,所述发光装置包括权利要求9所述的发光器件。
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