CN114685287B - 三芳胺化合物、包含该化合物的有机电致发光器件 - Google Patents

三芳胺化合物、包含该化合物的有机电致发光器件 Download PDF

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CN114685287B
CN114685287B CN202210409933.0A CN202210409933A CN114685287B CN 114685287 B CN114685287 B CN 114685287B CN 202210409933 A CN202210409933 A CN 202210409933A CN 114685287 B CN114685287 B CN 114685287B
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organic electroluminescent
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CN114685287A (zh
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王湘成
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Shanghai Yaoyi Electronic Technology Co ltd
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Abstract

本发明公开了三芳胺化合物、包含该化合物的有机电致发光器件，该化合物具有式(1)所示的结构，Ar11‑Ar22独立选自取代或未取代的芳基或杂芳基，L11‑L22独立选自单键、取代或未取代的亚芳基或亚杂芳基，A选自式(2)所示基团，X1‑X6中有且仅有一个为连接位点，其余位置独立选自氢、氘、卤素、C1‑C10烷基、C1‑C10烷氧基、C3‑C15环烷基、C2‑C15杂环烷基、C6‑C18芳基或C3‑C18杂芳基；Y1和Y2独立选自‑CR1R2‑、‑NR‑、O或S。上述化合物作为空穴传输材料用于有机电致发光器件，提高发光效率、使用寿命以及降低驱动电压，可用于有机光伏、平板显示和照明光源。

Description

三芳胺化合物、包含该化合物的有机电致发光器件
技术领域
本发明涉及有机发光材料领域，具体涉及三芳胺化合物、包含该化合物的有机电致发光器件。
背景技术
有机电致发光器件(OLED)具有亮度高、功耗低、质量轻、厚度薄、响应速度快、对比度高、可视角宽等优势，正受到学术界和产业界的广泛关注。目前常见的有机电致发光器件主要由电极、载流子传输层和发光层三部分构成，其中空穴传输层材料负责将阳极处的空穴传递至发光层，占据十分重要的地位。目前主要采用芳香胺化合物，这类分子具有良好的空穴传输特性，且前线轨道能级易于调节。例如，专利申请CN113816863A公开了三芳胺类化合物，以三芳胺为中心，在芴基的苯或9-位苯基上并有脂肪环，脂肪环相对于芳基具有更好的给电子能力，使得化合物具有良好的空穴传输性能以及热稳定性，同时能够为有机电致发光器件提供良好的使用寿命。专利申请CN113620818A公开了含稠环的三芳胺类化合物，以三芳胺为中心，同时连接苯并脂肪环和稠芳基基团，脂肪环相对于芳基具有推电子能力，使得化合物具有优异的空穴传输性能，稠芳基增加化合物的分子量，提高化合物的玻璃化转化温度，稳定性较好，是良好的空穴传输材料。专利申请CN113773207A通过将苯并五元/六元环结合到三芳胺中使得分子的空间构型更立体，提高空穴传输层与发光层之间的匹配性，并且有利于三线态能级(T1)的提高，从而有效地阻挡激子扩散，提高器件的效率。
目前，有机发光材料的研究已经在学术界和工业界广泛开展，大量性能优良的有机发光材料陆续被开发出来。总体来看，未来有机发光器件的方向是发展高效率、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。因此，设计与寻找一种稳定高效的有机化合物作为有机发光器件材料以克服其在实际应用过程中出现的不足，是有机发光器件研究中的重点与今后的研发趋势。
发明内容
本发明提供一种三芳胺化合物，该类化合物具有如式(1)所示的结构：
在式(1)中，L11、L12、L21和L22相同或不相同，各自独立选自单键、取代或未取代的C6-C30亚芳基、取代或未取代的C3-C30亚杂芳基；
Ar11、Ar12、Ar21和Ar22相同或不相同，各自独立选自取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基；
A选自如式(2)所示的基团：
在式(2)中，X1-X6中有且仅有一个为连接位点，其余位置相同或不相同，各自独立选自氢、氘、卤素、C1-C10烷基、C1-C10烷氧基、C3-C15环烷基、C2-C15杂环烷基、C6-C18芳基或C3-C18杂芳基；
Y1和Y2相同或不相同，各自独立选自-CR1R2-、-NR-、O或S；其中R1、R2和R各自独立选自氢、氘、C1-C10烷基、C3-C15环烷基、C2-C15杂环烷基、C6-C18芳基或C3-C18杂芳基。
作为优选，式(1)所示的三芳胺化合物具有如式(3)和式(4)所示的结构：
其中，L11、L12、L21和L22、Ar11、Ar12、Ar21和Ar22、A、X1-X6、Y1和Y2如上所述。
作为优选，在式(1)-(4)中，L11、L12、L21和L22各自独立选自单键、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、取代或未取代的亚芴基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚二苯并呋喃基，其中“取代或未取代的”中“取代的”表示被独立地选自由氘、氟、氰基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、甲氧基、乙氧基、甲硫基、乙硫基、环丁基、环戊基、环己基、苯基、萘基、联苯基、二苯并呋喃基、二苯并噻吩基、咔唑基中的一个或多个取代基所取代，且L11、L12、L21和L22中的取代基彼此相同或不相同。
作为优选，在式(1)-(4)中，Ar11、Ar12、Ar21和Ar22各自独立选自取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基，其中“取代或未取代的”中“取代的”表示被独立地选自由氘、氟、氰基、三甲基硅基、三氟甲基、C1-C6烷基、C3-C6环烷基、C1-C6烷氧基、C1-C6烷硫基、C6-C14芳基、C5-C14杂芳基中的一个或多个取代基所取代，且Ar11、Ar12、Ar21和Ar22中的取代基彼此相同或不相同。
作为优选，在式(1)-(4)中，Ar11、Ar12、Ar21和Ar22各自独立选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的噻吩基、取代或未取代的呋喃基、取代或未取代的硒吩基、取代或未取代的苯并噻吩基、取代或未取代的苯并呋喃基、取代或未取代的苯并硒吩基、取代或未取代的二苯并噻吩基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并硒吩基、取代或未取代的芴基、取代或未取代的硅芴基、取代或未取代的咔唑基、取代或未取代的苯并萘并噻吩基、取代或未取代的苯并萘并呋喃基、取代或未取代的苯并萘并硒吩基、取代或未取代的苯并芴基、取代或未取代的苯并咔唑基。
作为优选，式(1)所示的三芳胺化合物选自以下任一个化学结构：
本发明还提供一种有机材料，其包含上述任一所述三芳胺化合物，可以作为有机电致发光器件的空穴传输层材料。
本发明还提供一种有机电致发光器件，其包含上述任一所述三芳胺化合物或者所述有机材料。
与现有技术相比，本发明提供的三芳胺化合物作为空穴传输材料应用于有机光致发光器件，可以有效保证器件具有较高的空穴迁移率，并且有效地阻挡电子、激子进入到空穴传输层中，能够提高发光效率、器件寿命以及降低器件的驱动电压，可应用于有机光伏、平板显示、照明光源等领域。此外，本发明的三芳胺类有机化合物合成简单，易于产业化生产。
附图说明
图1是实施例中底部发光有机电致发光器件的结构示意图。
图2是实施例中顶部发光有机电致发光器件的结构示意图。
附图标记如下：101、基底层；102-第一电极(阳极)；103、空穴注入层；104、第一层空穴传输层；105、第二层空穴传输层；106、有机发光层；107、空穴阻挡层；；108、电子传输层；109、第二电极(阴极)；110、覆盖层。
具体实施方式
本发明式(1)所示的三芳胺化合物可通过本领域常规的偶联反应即制备得到，例如通过如下合成路线制备得到：
在化合物i和ii中，W1和W0中一个为卤素原子I或Br，另一个为硼酸基或片哪醇硼酯基；X1和X2均为卤素原子，且当W1和W0其中之一为I时，X1和X2相同或不同，可选为Br或Cl；当W1和W0其中之一为Br时，X1和X2均为Cl。
本发明的芳香胺类化合物可通过本领域常规的铃木偶联反应和布赫瓦尔德偶联反应得到，即：在惰性气体氛围下，多取代苯类化合物i与萘的衍生物ii通过铃木偶联反应得到中间体化合物MA；随后化合物MA通过两步布赫瓦尔德偶联反应，依次与胺类化合物iii和iv反应，在相应的催化剂、有机碱、配体、溶液以及相应温度下反应，经中间体化合物MB最终得到目标化合物。
本发明式(1)所示的三芳胺化合物合成路线、中间物质不局限于此，采用本领域熟知的其他合成手段获得目标化合物，均应在本发明的保护范围内。下面结合合成实施例说明本发明化合物的合成方法，其中未提及合成方法的化合物均通过商业途径获得。
(1)化合物HT-1的合成：
(1-1)中间体化合物MA-1的合成：
在氮气氛围下，向三口烧瓶中依次加入2,4-二氯苯硼酸(1.9g,10.0mmol,1eq)，5-溴苊(2.6g,11.1mmol,1.1eq)，碳酸钾(3.5g,25.3mmol,2.5eq)，四(三苯基膦)钯(57.8mg,0.05mmol,0.5％eq)，以及脱气的甲苯(50mL)、乙醇(30mL)和水(20mL)。上述混合体系在氮气氛围下回流反应12小时，冷却至室温后倒入80mL乙酸乙酯中，静置分层，用乙酸乙酯(3X80mL)萃取，合并所得有机相并用无水硫酸镁干燥，过滤并减压蒸馏除去溶剂。将所得粗产品用乙醇/正己烷的混合溶剂重结晶，得到化合物MA-1(2.4g，收率81.1％)。
(1-2)化合物HT-1的合成：
在氮气氛围下，向三口烧瓶中依次加入50mL无水甲苯、化合物MA-1(2.2g，7.5mmol,1eq)和N-苯基-4-联苯胺(4.6g，18.8mmol,2.5eq)，将混合物充分搅拌，再分别加入叔丁醇钠(1.1g，11.3mmol,1.5eq)，双二亚苄基丙酮钯(34mg，0.05mmol，0.7％eq)，和三叔丁基膦(10％正己烷溶液，0.26mL，0.11mmol，1.5％eq)。加热回流10小时后，通过薄层色谱法分析基本无原料化合物MA-9剩余，停止加热。当降温至45℃以下时，向反应体系加入5mL浓盐酸(37％H2O)和100mL去离子水的混合溶液，用分液漏斗分液，保留有机相，水相用甲苯(3×50mL)萃取，与前述保留有机相合并，蒸馏去除溶剂，粗产品依次经过硅胶柱层析分离(流动相为正己烷/二氯甲烷混合溶剂)，和乙醇/正己烷的混合溶剂重结晶，得到化合物HT-1(4.2g，收率78.1％)。两步反应总收率63.3％，质谱(m/z)＝717.32[M+H]+。
参照HT-1的制备方法合成HT-3、HT-5、HT-13、HT-16、HT-24、HT-25、HT-26、HT-27，不同之处在于使用原料iii-x等当量地代替N-苯基-4-联苯胺，其中使用的主要原料、合成的中间体及其收率如表1所示。
表1
参照HT-1的制备方法合成HT-30、HT-32、HT-83、HT-86、HT-98、HT-100，不同之处在于使用原料ii-x等当量地代替5-溴苊和原料iii-x等当量地代替N-苯基-4-联苯胺，其中使用的主要原料、合成的中间体及其收率如表2所示。
表2
(2)化合物HT-36的合成：
(2-1)中间体化合物MA-36的合成：
在氮气氛围下，依次将2-溴-4-氯-苯硼酸(2.3g，9.8mmol，1eq)、5-碘苊(2.7g，9.8mmol，1eq)、四(三苯基膦)钯(113.2mg，0.1mmol，1％eq)、碳酸钾(3.0g，21.6mmol,2.2eq)、四丁基溴化铵(632mg，2.0mmol，0.2eq)、脱气处理的甲苯(40mL)、乙醇(10mL)和去离子水(10mL)加入三口烧瓶中。氮气氛围下升温至回流，搅拌10小时后停止加热。将反应体系冷却至室温，倒入乙酸乙酯(3×70mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗产品经过乙醇/正庚烷混合溶剂体系重结晶提纯，得到化合物MA-36(2.7g，收率80.4％)。
(2-2)中间体化合物MB-36的合成：
在氮气氛围下，向三口烧瓶中依次加入化合物MA-36(2.5g,7.4mmol，1eq)、二(4-联苯基)胺(2.4g,7.4mmol,1eq)、叔丁醇钠(840mg,8.8mmol,1.2eq)、双(三叔丁基膦)钯(75.6mg，0.15mmol,2％mol)，和无水甲苯(50mL)，搅拌并升温至回流。9小时后停止加热，将反应体系冷却至室温，使用二氯甲烷(3×60mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗品依次经过硅胶柱色谱提纯(流动相为正己烷/二氯甲烷混合溶剂)，和乙醇/正己烷混合溶剂体系重结晶提纯，得到化合物MB-36(3.2g,74.1％)。
(2-3)化合物HT-36的合成：
在氮气氛围下，向三口烧瓶中依次加入40mL无水甲苯、化合物MA-36(3.0g，5.1mmol,1eq)和N-苯基-2(9,9-二甲基-9H-芴)胺(1.6g，5.6mmol,1.1eq)，将混合物充分搅拌，再分别加入叔丁醇钠(733mg，7.6mmol,1.5eq)，双二亚苄基丙酮钯(34mg，0.05mmol，1％eq)，和三叔丁基膦(10％正己烷溶液，0.18mL，0.077mmol，1.5％eq)。加热回流9小时后，通过薄层色谱法分析基本无原料化合物MB-36剩余，停止加热。当降温至45℃以下时，向反应体系加入5mL浓盐酸(37％H2O)和90mL去离子水的混合溶液，用分液漏斗分液，保留有机相，水相用甲苯(3×50mL)萃取，与前述保留有机相合并，蒸馏去除溶剂，粗产品依次经过硅胶柱层析分离(流动相为正己烷/二氯甲烷混合溶剂)，和乙醇/正己烷的混合溶剂重结晶，得到化合物HT-36(3.3g，收率77.6％)，三步反应总收率46.2％，质谱(m/z)＝833.38[M+H]+。
参照HT-36的制备方法合成HT-35、HT-40、HT-41、HT-45、HT-46、HT-51、HT-55，不同之处在于使用原料iii-x等当量地代替二(4-联苯基)胺和原料iv-x等当量地代替N-苯基-2(9,9-二甲基-9H-芴)胺，其中使用的主要原料、合成的中间体及其收率如表3所示。
表3
(3)化合物HT-117的合成：
(3-1)中间体化合物MA-117的合成：
参照化合物MA-1的制备方法合成中间体化合物MA-117。不同之处在于使用原料3,5-二氯苯硼酸等当量地代替2-溴-4-氯-苯硼酸。
(3-2)中间体化合物MB-117的合成：
参照从中间体化合物MB-1制备得到化合物HT-1的方法，合成中间体化合物MB-117。不同之处在于使用中间体化合物MA-117等当量地代替化合物MB-1和胺类化合物iii-117代替N-苯基-4-联苯胺(iv-1)，并且iii-117与MA-117的物质的量之比为1:1。
(3-3)化合物HT-117的合成：
参照从中间体化合物MB-1制备得到化合物HT-1的方法，合成化合物HT-117。不同之处在于，使用中间体化合物MB-117等当量地代替化合物MB-1和使用胺类化合物iv-117代替N-苯基-4-联苯胺(iv-1)，并且iv-117与MB-117的物质的量之比为1:1，三步反应总收率48.0％，质谱(m/z)＝887.39[M+H]+。
参照HT-117的方法合成HT-115、HT-118、HT-120、HT-122、HT-123、HT-124、HT-127、HT-134、HT-139、HT-145、HT-147、HT-150、HT-151、HT-153，不同之处在于使用原料iii-x等当量地代替iii-117、原料iv-x等当量地代替iv-117，其中使用的主要原料、合成的中间体及其收率如表4所示。
表4
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参照HT-117的方法合成HT-172、HT-174、HT-180、HT-193、HT-196、HT-207，不同之处在于使用原料ii-x等当量地代替5-溴苊、原料iii-x等当量地代替iii-117和原料iv-x等当量地代替iv-117，其中使用的主要原料、合成的中间体及其收率如表5所示。
表5
蓝光器件实施例1：蓝色有机电致发光器件的制备
按照如图2所示的结构制作蓝色顶部发光有机电致发光器件，制备工艺为：在玻璃材质的基底101上，形成透明阳极ITO膜层，膜厚150nm，得到第一电极102作为阳极，之后蒸镀化合物1与本发明化合物HT-1的混合材料作为空穴注入层103，混合比例为3:97(质量比)，厚度为10nm，之后蒸镀100nm厚度的化合物HT-1，得到第一层空穴传输层104，然后蒸镀20nm厚度的化合物1-2，得到第二层空穴传输层105，然后以95:5的蒸镀速率蒸镀化合物1-3与化合物1-4(厚度30nm)，制作蓝光发光单元106。然后依次蒸镀10nm厚度的化合物5形成空穴阻挡层107，以及混合比例为4:6(质量比)的化合物6和LiQ形成电子传输层108(厚度30nm)。之后依次将厚度为3nm厚度镱(Yb)，厚度为10nm的镁(Mg)和银(Ag)以1∶9的蒸镀速率真空蒸镀在电子注入层上，作为第二电极109，随后蒸镀70nm的化合物7作为覆盖层材料，完成有机电致发光器件的制造。
表6
蓝光器件实施例2-19
除了在形成空穴注入层和空穴传输层时，分别以表7中化合物替代化合物HT-2外，采用与蓝光器件实施例1相同的方法制作有机电致发光器件。
比较例1-2
除了在形成空穴注入层和空穴传输层时，分别以化合物HT-A、化合物HT-B替代化合物HT-2外，采用与蓝光器件实施例1相同的方法制作有机电致发光器件。
对如上制得的有机电致发光器件，其工作电压和效率通过计算机控制的Keithley2400测试系统计算得到。黑暗条件下的器件寿命使用配备电源和光电二极管作为检测单元的Polaronix(McScience Co.)寿命测量系统得到。每一组蓝光器件实施例、对比例2的器件均与对比例1的器件在同一批次中产出并测试，将对比例1的器件工作电压、效率和寿命均分别记为1，并分别计算蓝光器件实施例1-19、对比例2与对比例1的器件相应指标的比值，如表7所示。
表7
空穴传输层 相对工作电压 相对效率 相对寿命
对比例1 HT-A 1 1 1
对比例2 HT-B 1.049 0.943 1.026
蓝光器件实施例1 HT-3 0.971 1.149 1.272
蓝光器件实施例2 HT-24 0.909 1.105 1.384
蓝光器件实施例3 HT-25 0.968 1.112 1.205
蓝光器件实施例4 HT-32 0.916 1.160 1.295
蓝光器件实施例5 HT-35 0.973 1.098 1.489
蓝光器件实施例6 HT-36 0.945 1.137 1.321
蓝光器件实施例7 HT-41 0.977 1.109 1.179
蓝光器件实施例8 HT-55 0.931 1.128 1.375
蓝光器件实施例9 HT-86 0.890 1.076 1.178
蓝光器件实施例10 HT-115 0.954 1.153 1.253
蓝光器件实施例11 HT-118 0.942 1.170 1.113
蓝光器件实施例12 HT-122 0.949 1.093 1.391
蓝光器件实施例13 HT-134 0.960 1.148 1.219
蓝光器件实施例14 HT-145 0.921 1.100 1.330
蓝光器件实施例15 HT-147 0.906 1.086 1.435
蓝光器件实施例16 HT-150 0.969 1.121 1.186
蓝光器件实施例17 HT-151 0.933 1.168 1.312
蓝光器件实施例18 HT-193 0.927 1.135 1.288
蓝光器件实施例19 HT-196 0.919 1.090 1.400
红光器件实施例1：红色有机电致发光器件的制备
按照如图1所示的结构制作红色底部发光有机电致发光器件，制备工艺为：在玻璃材质的基底101上，形成透明阳极ITO膜层(厚度150nm)，得到第一电极102作为阳极。随后通过真空蒸镀的方法，在阳极表面蒸镀表6中所述化合物1与化合物2-2的混合材料作为空穴注入层103，混合比例为3:97(质量比)，厚度为10nm。随后在空穴注入层上蒸镀100nm厚度的化合物2-2，得到第一层空穴传输层104。随后在第一空穴传输层上蒸镀10nm厚度的本发明化合物HT-3，得到第二层空穴传输层105。在第二空穴传输层上，将化合物2-3和化合物2-4以95:5的质量比进行共蒸镀，形成厚度为40nm的有机发光层106。然后，在有机发光层上，依次蒸镀化合物5形成空穴阻挡层107(厚度10nm)，以及混合比例为4:6(质量比)的化合物6和LiQ形成电子传输层108(厚度30nm)。最后将镁(Mg)和银(Ag)以1∶9的蒸镀速率混合，真空蒸镀在电子注入层上，作为第二电极109，完成有机电致发光器件的制造。
红光器件实施例2-25
除了在形成第二空穴传输层时，分别以表9中化合物替代化合物HT-3外，采用与红光器件实施例1相同的方法制作有机电致发光器件。
比较例1-2
除了在形成第二空穴传输层时，分别以化合物HT-A、化合物HT-B替代化合物HT-13外，采用与红光器件实施例1相同的方法制作有机电致发光器件。
以上红光器件实施例和对比例使用的主要材料结构如表8所示。
表8
对如上制得的有机电致发光器件，其工作电压和效率通过计算机控制的Keithley2400测试系统计算得到。黑暗条件下的器件寿命使用配备电源和光电二极管作为检测单元的Polaronix(McScience Co.)寿命测量系统得到。每一组红光器件实施例和对比例4的器件均与对比例3的器件在同一批次中产出并测试，将对比例3的器件的工作电压、效率和寿命均分别记为1，并分别计算红光器件实施例1-25、对比例4与对比例3的器件相应指标的比值，如表9所示。
表9
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综上所述，本发明的三芳胺类有机化合物作为有机电致发光器件的空穴传输层材料可以保证器件具有较高的空穴迁移率，且能有效阻挡电子和激子进入到空穴传输层中，进而提高器件的发光效率，同时分子的稳定性高，进一步提高器件的使用寿命。
以上所述，仅为本发明较佳的具体实施方式，但本发明的保护范围并不局限于此，任何熟悉本技术领域的技术人员在本发明揭露的技术范围内，根据本发明的技术方案及其发明构思加以等同替换或改变，都应涵盖在本发明的保护范围之内。

Claims (5)

1.三芳胺化合物，其特征在于，选自以下任一个化学结构：
2.一种有机材料，包括权利要求1所述三芳胺化合物中的一种或多种。
3.一种有机电致发光器件，包括权利要求1所述三芳胺化合物中的一种或多种、或者权利要求2所述有机材料。
4.根据权利要求3所述的有机电致发光器件，其特征在于，包括基板、第一电极、包含发光层和空穴传输层在内的一层以上有机层和第二电极元件，其中所述空穴传输层材料含有权利要求1所述有机化合物中的一种或多种，或者权利要求2所述有机材料。
5.一种显示或照明装置，其特征在于，包括权利要求3或4所述的有机电致发光器件。
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