CN110577511A - 一种以三芳胺结构为核心的化合物及其制备方法 - Google Patents
一种以三芳胺结构为核心的化合物及其制备方法 Download PDFInfo
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- CN110577511A CN110577511A CN201910490021.9A CN201910490021A CN110577511A CN 110577511 A CN110577511 A CN 110577511A CN 201910490021 A CN201910490021 A CN 201910490021A CN 110577511 A CN110577511 A CN 110577511A
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Classifications
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- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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Abstract
本发明公开了一种以三芳胺结构为核心的化合物及其制备方法与应用,该化合物结构如通式(1)所示。本发明提供的化合物具有较高的玻璃化温度和分子热稳定性,合适的HOMO和LUMO能级,较高迁移率,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。
Description
技术领域
本发明涉及有机电致发光材料技术领域,尤其是涉及一种结构中含有三芳胺的化合物及其制备方法。
背景技术
有机电致发光(OLED:Organic Light Emission Diodes)器件技术既可以用来制造新型显示产品,也可以用于制作新型照明产品,有望替代现有的液晶显示和荧光灯照明,应用前景十分广泛。
OLED发光器件犹如三明治的结构,包括电极材料膜层,以及夹在不同电极膜层之间的有机功能材料,各种不同功能材料根据用途相互叠加在一起共同组成OLED发光器件。作为电流器件,当对OLED发光器件的两端电极施加电压,并通过电场作用有机层功能材料膜层中的正负电荷,正负电荷进一步在发光层中复合,即产生OLED电致发光。
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,使用寿命等性能还需要进一步提升。
对于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OLED的功能材料。
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,即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特性,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要求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含空穴注入材料,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,具有高性能的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三芳胺结构为核心的化合物及其制备方法。
本发明的技术方案如下:
一种以三芳胺结构为核心的化合物,所述化合物的结构如通式(1)所示:
其中,m、n分别独立地表示为数字1、2或3;
R1、R2、R3、R4分别独立地表示为取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的萘基、通式(2)或通式(3)所示的结构,且R3、R4互为邻位;
通式(2)、通式(3)中,L1、L2分别独立地表示为单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基;
通式(2)中,X表示为-O-、-S-、-C(R5)(R6)-或-N(R7)-;
Z1-Z8分别独立地表示为CH或N,且至多有4个N;
通式(2)与L1键合的位点Z5或Z6或Z7或Z8表示为碳原子;
通式(3)中,Y1-Y8分别独立地表示为CH或N,且至多有4个N。
所述R5~R7分别独立的表示为C1-20的烷基、C6-30芳基、含有一个或多个杂原子取代或未取代的5~30元杂芳基中的一种;其中R5与R6可相连形成5元至30元脂环或芳环;
所述取代基为卤素、氰基、C1-10烷基或C6-20芳基。
优选方案,所述R5~R7分别独立地表示为甲基、乙基、丙基、异丙基、丁基、叔丁基、戊基、苯基、联苯基、三联苯基、萘基、吡啶基或呋喃基。
优选方案,所述通式(2)所示结构为:
中的任一种。
优选方案,所述通式(3)所示结构为:
中的任一种。
所述以三芳胺结构为核心的化合物优选的具体结构为:
中的任一种。
一种所述以三芳胺结构为核心的化合物的制备方法,所述制备方法涉及的反应过程如下:
具体制备过程包括如下:
(1)以反应物A与反应物B为原料,甲苯为溶剂,在氮气的氛围下向反应体系中加入Pd2(dba)3、P(t-Bu)3和叔丁醇钠,95~110℃下反应10~24h,自然冷却至室温,并过滤反应溶液,滤液进行减压旋蒸,过中性硅胶柱,得到中间产物M;所述甲苯用量为每克反应物A使用50~80ml;所述反应物A与反应物B的摩尔比为1:0.8~1;所述Pd2(dba)3与反应物A的摩尔比为0.005~0.01:1;所述P(t-Bu)3与反应物A的摩尔比为1.5~3.0:1;所述叔丁醇钠与反应物A的摩尔比为2~2.5:1;
(2)以步骤(1)得到的中间产物M与反应物C为原料,甲苯为溶剂,在氮气的氛围下向反应体系中加入Pd2(dba)3、P(t-Bu)3和叔丁醇钠,95~110℃下反应10~24h,自然冷却至室温,并过滤反应溶液,滤液进行减压旋蒸,过中性硅胶柱,得到通式(1)所示化合物;所述甲苯用量为每克中间产物M使用50~80ml;所述中间产物M与反应物C的摩尔比为1:1.0~1.5;所述Pd2(dba)3与中间产物M的摩尔比为0.005~0.01:1;所述P(t-Bu)3与中间产物M的摩尔比为1.5~3.0:1;所述叔丁醇钠与中间产物M的摩尔比为2~2.5:1。
一种有机电致发光器件,所述有机电致发光器件至少一层功能层含有所述以三芳胺结构为核心的化合物。
一种有机电致发光器件,所述以三芳胺结构为核心的化合物作为空穴传输层或者电子阻挡层材料,用于制作有机电致发光器件。
一种照明或显示元件,所述元件包含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、***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。
本发明有益的技术效果在于:
本发明化合物中的p-π共轭效应使得其有很强的空穴传输能力,高的空穴传输速率能够提高有机电致发光器件的效率;化合物中不对称的三芳胺结构能够降低分子的结晶性,降低分子的平面性,阻止分子在平面上移动从而提高了分子的热稳定性。
本发明的化合物的结构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,同时该类三芳胺类结构具有较高的迁移率和三线态能级,可以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。
本发明的化合物在OLED器件应用时,通过器件结构优化,可保持高的膜层稳定性,可有效提升OLED器件的光电性能以及OLED器件的寿命。本发明所述化合物在OLED发光器件中具有良好的应用效果和产业化前景。
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;
其中,1、透明基板层,2、ITO阳极层,3、空穴注入层,4、空穴传输层,5、电子阻挡层,6、发光层,7、空穴阻挡/电子传输层,8、电子注入层,9、阴极反射电极层。
图2为本发明OLED器件在不同温度下测量的效率曲线图。
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。
实施例1:化合物1的合成
(1)在250ml的三口瓶中,通氮气保护下,加入0.01mol反应物A-1,0.01mol反应物B-1,150ml甲苯搅拌混合,然后加入5×10-5mol Pd2(dba)3,5×10-5mol P(t-Bu)3,0.03mol叔丁醇钠,加热至105℃,回流反应24小时,取样点板,显示无溴代物剩余,反应完全;自然冷却至室温,过滤,滤液旋蒸至无馏分,过中性硅胶柱,得到中间产物M-1,HPLC纯度99.66%,收率86.8%。HRMS(EI):材料分子量为410.1539,实测分子量410.1529;
(2)在250ml的三口瓶中,通氮气保护下,加入0.01mol的步骤(1)得到的中间产物M-1与0.01mol反应物C,150ml甲苯搅拌混合,然后加入5×10-5molPd2(dba)3,5×10-5mol P(t-Bu)3,0.03mol叔丁醇钠,加热至105℃,回流反应24小时,取样点板,反应完全;自然冷却至室温,过滤,滤液旋蒸至无馏分,过中性硅胶柱,得到中间产物M-1,HPLC纯度99.25%,收率84.5%。HRMS(EI):材料分子量为729.2668,实测分子量729.2649。
重复实施例1的制备过程合成以下化合物,不同之处在于使用如下表1中所列的反应物A、反应物B和反应物C;
表1
上述反应中的反应物A、反应物B、反应物C为市场上购买,或通过suzuki反应碳碳偶联或乌尔曼碳氮偶联反应一步或多步骤合成制得;
以反应物的合成为例:
(1)在250ml的反应瓶中加入0.1mol2,5-二溴碘苯,0.1mol的苯硼酸,100ml的四氢呋喃(THF),在氮气的氛围下,向反应体系中加入0.001mol Pd(PPh3)4和2M碳酸钾水溶液20ml,在氮气保护下,反应体系于70~90℃,反应10~24h,自然冷却至室温,并过滤反应溶液,滤液进行减压旋蒸,过中性硅胶柱,得2,5-二溴联苯,HPLC纯度99.25%,收率98.0%;
(2)在250ml的三口瓶中,通氮气保护下,加入0.01mol的步骤(1)得到的中间产物2,5-二溴联苯与0.01mol咔唑,150ml甲苯搅拌混合,然后加入5×10-5mol Pd2(dba)3,5×10-5mol P(t-Bu)3,0.03mol叔丁醇钠,加热至105℃,回流反应24小时,取样点板,反应完全;自然冷却至室温,过滤,滤液旋蒸至无馏分,过中性硅胶柱,得到反应物C-3,HPLC纯度99.65%,收率82.5%。HRMS(EI):材料分子量为397.0466,实测分子量397.0449。
本发明化合物在发光器件中作为空穴传输层材料使用。对本发明上述实施例制备的化合物分别进行热性能、T1能级、HOMO能级的测试,检测结果如表2所示。
表2
化合物 | Tg(℃) | Td(℃) | T1(eV) | HOMO(ev) |
化合物107 | 138 | 408 | 2.59 | 5.54 |
化合物117 | 139 | 411 | 2.63 | 5.67 |
化合物128 | 142 | 408 | 2.58 | 5.56 |
化合物130 | 140 | 410 | 2.65 | 5.65 |
化合物154 | 146 | 411 | 2.64 | 5.61 |
化合物163 | 153 | 418 | 2.67 | 5.69 |
化合物173 | 148 | 414 | 2.61 | 5.63 |
化合物177 | 157 | 419 | 2.63 | 5.52 |
化合物181 | 153 | 422 | 2.58 | 5.49 |
注:三线态能级T1是由日立的F4600荧光光谱仪测试,材料的测试条件为2*10-5的甲苯溶液;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***(IPS3)测试,测试为大气环境。
由上表2数据可知,本发明的有机化合物具有较为合适的HOMO能级,可应用于空穴传输层,本发明以三芳胺为核心的有机化合物具有较高的三线态能级及较高的热稳定性,使得所制作的含有本发明有机化合物的OLED器件效率和寿命均得到提升。
以下通过器件实施例1~16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层材料的应用效果。器件实施例2~16、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,并且所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和电子阻挡层材料发生了改变。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
使用ITO作为阳极,Al作为阴极,GH-1、GH-2和GD-1按重量比45:45:10混掺作为发光层材料,HAT-CN作为空穴注入层材料,本发明实施例制备的化合物6作为空穴传输层材料,EB-1作为电子阻挡层材料,ET-1和Liq作为电子传输层材料,LiF作为电子注入层材料。具体的制作步骤如下:
a)清洗透明基板层1上的ITO阳极层2,分别用去离子水、丙酮、乙醇超声清洗各15分钟,然后在等离子体清洗器中处理2分钟;
b)在ITO阳极层2上,通过真空蒸镀方式蒸镀空穴注入层材料HAT-CN,厚度为10nm,这层作为空穴注入层3;
c)在空穴注入层3上,通过真空蒸镀方式蒸镀空穴传输层材料化合物6,厚度为60nm,该层为空穴传输层4;
d)在第一空穴传输层4上,通过真空蒸镀方式蒸镀电子阻挡层材料EB-1,厚度为20nm,该层为电子阻挡层5;
e)在电子阻挡层5上蒸镀发光层6,主体材料为GH-1和GH-2,掺杂材料为GD-1,GH-1、GH-2和GD-1的质量比为45:45:10厚度为30nm;
f)在发光层6之上,通过真空蒸镀方式蒸镀电子传输材料ET-1和Liq,两者质量比为1:1,厚度为40nm,这层有机材料作为空穴阻挡/电子传输层7使用;
g)在空穴阻挡/电子传输层7之上,真空蒸镀电子注入层LiF,厚度为1nm,该层为电子注入层8;
h)在电子注入层8之上,真空蒸镀阴极Al(100nm),该层为阴极反射电极层9。
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
表4
由表4器件数据结果可以看出,本发明的有机发光器件无论是在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、7、11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、7、11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。
以上所述仅为本发明的较佳实施例,并不用以限制本发明,凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (9)
1.一种以三芳胺结构为核心的化合物,其特征在于,所述化合物的结构如通式(1)所示:
其中,m、n分别独立地表示为数字1、2或3;
R1、R2、R3、R4分别独立地表示为取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的萘基、通式(2)或通式(3)所示的结构,且R3、R4互为邻位;
通式(2)、通式(3)中,L1、L2分别独立地表示为单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基;
通式(2)中,X表示为-O-、-S-、-C(R5)(R6)-或-N(R7)-;
Z1-Z8分别独立地表示为CH或N,且至多有4个N;
通式(2)与L1键合的位点Z5或Z6或Z7或Z8表示为碳原子;
通式(3)中,Y1-Y8分别独立地表示为CH或N,且至多有4个N。
所述R5~R7分别独立的表示为C1-20的烷基、C6-30芳基、含有一个或多个杂原子取代或未取代的5~30元杂芳基中的一种;其中R5与R6可相连形成5元至30元脂环或芳环;
所述取代基为卤素、氰基、C1-10烷基或C6-20芳基。
2.根据权利要求1的所述的化合物,其特征在于,所述R5~R7分别独立地表示为甲基、乙基、丙基、异丙基、丁基、叔丁基、戊基、苯基、联苯基、三联苯基、萘基、吡啶基或呋喃基。
3.根据权利要求1所述的化合物,其特征在于,所述通式(2)所示结构为:
中的任一种。
4.根据权利要求1所述的化合物,其特征在于,所述通式(3)所示结构为:
中的任一种。
5.根据权利要求1所述的化合物,其特征在于,所述化合物的具体结构为:
中的任一种。
6.一种权利要求1~5任一项所述化合物的制备方法,其特征在于,所述制备方法涉及的反应过程如下:
具体制备过程包括如下:
(1)以反应物A与反应物B为原料,甲苯为溶剂,在氮气的氛围下向反应体系中加入Pd2(dba)3、P(t-Bu)3和叔丁醇钠,95~110℃下反应10~24h,自然冷却至室温,并过滤反应溶液,滤液进行减压旋蒸,过中性硅胶柱,得到中间产物M;所述甲苯用量为每克反应物A使用50~80ml;所述反应物A与反应物B的摩尔比为1:0.8~1;所述Pd2(dba)3与反应物A的摩尔比为0.005~0.01:1;所述P(t-Bu)3与反应物A的摩尔比为1.5~3.0:1;所述叔丁醇钠与反应物A的摩尔比为2~2.5:1;
(2)以步骤(1)得到的中间产物M与反应物C为原料,甲苯为溶剂,在氮气的氛围下向反应体系中加入Pd2(dba)3、P(t-Bu)3和叔丁醇钠,95~110℃下反应10~24h,自然冷却至室温,并过滤反应溶液,滤液进行减压旋蒸,过中性硅胶柱,得到通式(1)所示化合物;所述甲苯用量为每克中间产物M使用50~80ml;所述中间产物M与反应物C的摩尔比为1:1.0~1.5;所述Pd2(dba)3与中间产物M的摩尔比为0.005~0.01:1;所述P(t-Bu)3与中间产物M的摩尔比为1.5~3.0:1;所述叔丁醇钠与中间产物M的摩尔比为2~2.5:1。
7.一种有机电致发光器件,其特征在于,所述有机电致发光器件至少一层功能层含有权利要求1~5任一项所述的以三芳胺结构为核心的化合物。
8.根据权利要求7所述的有机电致发光器件,其特征在于,所述三芳胺为核心的化合物作为空穴传输层或者电子阻挡层材料,用于制作有机电致发光器件。
9.一种照明或显示元件,其特征在于,所述元件包含权利要求7或8所述的有机电致发光器件。
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