CN112538022A - 一种新型空穴传输材料及其应用 - Google Patents

一种新型空穴传输材料及其应用 Download PDF

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CN112538022A
CN112538022A CN201910900883.4A CN201910900883A CN112538022A CN 112538022 A CN112538022 A CN 112538022A CN 201910900883 A CN201910900883 A CN 201910900883A CN 112538022 A CN112538022 A CN 112538022A
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hole transport
transport material
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孟鸿
王涛
贺耀武
胡钊
刘铭
缪景生
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Peking University Shenzhen Graduate School
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Peking University Shenzhen Graduate School
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Abstract

本发明提供了一种新型空穴传输材料及其应用，涉及有机光电材料技术领域。本发明的空穴传输材料通过在不同的芳环母体结构上连接间位二取代芳胺的苯基配体，调节该空穴传输材料的分子量、π共轭程度和分子刚性。其载流子传输能力强，有利于空穴传输，且可以提高玻璃化转变温度，不易于结晶，成膜性优良。与现有技术相比，含有本发明新型空穴传输材料的有机电致发光器件，具有较高的发光效率和较高长的使用寿命。

Description

一种新型空穴传输材料及其应用
技术领域
本发明涉及有机光电材料技术领域，具体涉及一种新型空穴传输材料及其应用。
背景技术
有机发光二极管(Organic Light-Emitting Diode,OLED)是新一代显示和照明技术，具有主动发光、宽视角、高对比度、快速响应、轻质低能耗、低驱动电压、广色域、制造工艺简单和可实现柔性显示等优点，在平板显示、照明等领域有着广泛的应用前景。近年来已经受到了全世界范围的关注，并逐步在智能手机、电脑、可穿戴设备等方面得到越来越多的应用。
有机发光器件结构一般包括阳极、阴极和介于两者之间的有机功能层，有机功能层主要包括发光层、用于电荷注入的电子注入层和空穴注入层，用于电荷传输的电子传输层和空穴传输层。目前OLED的大规模应用受到较大的限制，原因就在于各有机功能层的性能还与实际需求有较大差距。如，发光层的效率和稳定性直接影响OLED器件的寿命和效率，电子传输层和空穴传输层的传输速度差别较大引起的激子猝灭也会使器件光色不均匀和降低器件效率，各功能层间的界面情况难以控制限制了大规模生产等。随着市场对于OLED器件要求的逐渐提高，开发新型的空穴传输材料是一种提高和优化有机电致发光器件性能的重要手段，对OLED器件的推广应用有着重要的意义。
目前广泛使用的空穴传输材料α-NPB在光电性能方面还有很大的提升空间，其主要缺点是Tg(玻璃化转变温度)仅为98℃，在制备和使用过程中都容易发生结晶，影响空穴传输效率和缩短器件寿命。同时，由于电子传输材料的电子传输效率通常都高于空穴传输材料，当提高空穴传输材料的空穴传输效率时就可以显著提高器件的光电效率。因此，开发具有高玻璃化转变温度和高空穴迁移率的新型空穴传输材料，对OLED器件光电性能和稳定性的提高具有重要意义。
发明内容
本发明所要解决的技术问题之一在于：提供一种新型空穴传输材料，解决现有空穴传输材料玻璃化转变温度低、空穴传输效率不够的问题。
本发明所要解决的技术问题之二在于：提供一种使用了该新型空穴传输材料的有机电致发光器件，解决现有有机电致发光器件发光效率不足、使用寿命短的问题。
本发明提供了一种新型空穴传输材料和基于有机无机复合空穴传输材料的有机电致发光器件，涉及有机光电材料技术领域。本发明通过在不同的芳环母体结构上连接间位二取代芳胺的苯基配体，调节该空穴传输材料的分子量、π 共轭程度和分子刚性。其载流子传输能力强，有利于空穴传输，且可以提高玻璃化转变温度，不易于结晶，成膜性优良。与现有技术相比，本发明是基于上述新型空穴传输材料，含有本发明的新型空穴传输材料的有机电致发光器件，具有较高的发光效率和较高长的使用寿命。
本发明提供了一种新型空穴传输材料，其分子结构通式如化学式Ⅰ所示：
Figure BDA0002211779350000021
其中，Ar选自取代或未取代的C6～C60芳基、取代或未取代的C10～C60稠环基、取代或未取代的C3～C60螺环基、取代或未取代的C3～C60杂环基。R1、R2独立地选自取代或未取代的C6～C60芳基、取代或未取代的C10～C60稠环基。
优选的，Ar选自取代或未取代的C6～C30芳基、取代或未取代的C10～C30稠环基、取代或未取代的C4～C30螺环基、取代或未取代的C4～C30杂环基。R1、R2独立地选自取代或未取代的C6～C30芳基、取代或未取代的C10～C30稠环基。
优选的，Ar选自如下结构中的任意一种：
Figure BDA0002211779350000031
Figure BDA0002211779350000041
Figure BDA0002211779350000051
Figure BDA0002211779350000061
Figure BDA0002211779350000071
Figure BDA0002211779350000081
优选的，本发明提供的所述空穴传输材料，选自如下化学结构中的任意一种：
Figure BDA0002211779350000091
Figure BDA0002211779350000101
Figure BDA0002211779350000111
Figure BDA0002211779350000121
Figure BDA0002211779350000131
Figure BDA0002211779350000141
Figure BDA0002211779350000151
Figure BDA0002211779350000161
Figure BDA0002211779350000171
Figure BDA0002211779350000181
本发明所述的有机电致发光器件，包括阴极、阳极、电荷传输层、电荷阻挡层、发光层等多个有机功能层，所述有机功能层至少含有本发明所述的一种新型空穴传输材料。
优选的，所述的一种有机电致发光材料在电致发光器件中用作空穴传输层材料。例如，所述有机功能层包括电荷传输层，电荷传输层包括空穴传输层和电子传输层；所述有机功能层至少含有本发明所述的一种新型空穴传输材料。
实施本发明，具有如下有益效果：
本发明提供了一种新型空穴传输材料和基于该新型空穴传输材料的有机电致发光器件，涉及有机光电材料技术领域。本发明通过在不同的芳环母体结构上连接间位二取代芳胺的苯基配体，调节该空穴传输材料的分子量、π共轭程度和分子刚性。其载流子传输能力强，有利于空穴传输，且可以提高玻璃化转变温度，不易于结晶，成膜性优良。与现有技术相比，含有本发明的新型空穴传输材料的有机电致发光器件，具有较高的发光效率和较高长的使用寿命。
具体实施方式
下面结合具体实施例对本发明的技术方案进行详细的说明，但是所述实施例的说明，仅仅是本发明的一部分实施例，其中大部分并不仅限于此。
本发明所述的一种新型空穴传输材料，可以通过如下反应制备得到：
Figure BDA0002211779350000191
本发明式(Ⅰ)所示一种新型空穴传输材料，可以通过Buchwald-Hartwig偶联和Suzuki偶联制备得到，采用的是本领域研究人员所熟知的常规反应条件。本发明对于上述各种反应所采用的原料没有特殊的限制，采用市售产品或本领域研究人员常用的合成方法制备得到。
本发明所提供的有机电致发光器件可以应用于智能设备显示、室内和室外照明、光电耦合器件、可穿戴设备等领域。
实施例1：化合物1的制备
Figure BDA0002211779350000192
步骤1，取1,3-二溴-5-氯苯(19.85g，73.4mmol)，N-苯基-1-萘胺(32.19g，146.8mmol)，叔丁醇钠(21.14g，220.2mmol)加入三口烧瓶中，加入甲苯并通氮气20min。然后向三口烧瓶中加入催化剂二氯,二叔丁基-(4-二甲基氨基苯基)磷钯(II)(0.52g，0.734mmol)，继续通氮气20min，回流温度下反应24h。反应结束后，过滤得有机相，浓缩，粗产品过硅胶柱，得到化合物1-1(28.88g，产率72％)。
步骤2，取化合物1-1(27.35g，50mmol)，联硼酸频那醇酯(15.25g，60mmol)，醋酸钾(4.91g，150mmol)加入三口烧瓶中，加入干燥的1，4-二氧六环溶解并通氮气20min。取三(二亚苄基丙酮)二钯(2.29g，2.5mmol)和2-二环己基磷-2′,4′,6′-三异丙基联苯(2.39g，5mmol)加入三口烧瓶中，继续通氮气20min，升温至120℃，反应12h。反应结束后，用去离子水洗涤三次，过滤，干燥。粗产品过硅胶柱，得到化合物1-2(27.1g，产率85％)
步骤3，取化合物1-2(25.51g，40mmol)，1，4-二溴苯(4.718g，20mmol)和四三苯基膦钯(2.31g，2mmol)加入三口烧瓶中，加入80mL甲苯溶解并通氮气20min。另取碳酸钾(16.59g，120mmol)溶于20mL去离子水中，加入三口烧瓶中并继续通氮气20min。在回流温度下反应12h。反应结束后加入去离子水洗涤，分离得到有机相，干燥，浓缩。粗产品过硅胶柱，得到化合物1(19.13g，产率87％)质谱m/z：理论值：1098.47；实测值：1098.49。理论元素含量(％)C82H58N4：C，89.59；H，5.32；N，5.10；实测元素含量(％)：C，89.57；H，5.35；N，5.08。上述结果证明获得产物为目标化合物。
实施例2：化合物2的制备
将实施例1中的1,4-二溴苯更换成2,4-二溴联苯。其他步骤同实施例1。质谱m/z：理论值：1174.50；实测值：1175.50。理论元素含量(％)C88H62N4：C，89.92；H，5.32；N，4.77；实测元素含量(％)：C，89.93；H，5.36；N，4.75。上述结果证明获得产物为目标化合物。
实施例3：化合物3的制备
将实施例1中的1,4-二溴苯更换成1,4-二溴-2,5-二苯基苯。其他步骤同实施例1。质谱m/z：理论值：1250.53；实测值：1250.53。理论元素含量(％)C94H62N4：C，90.21；H，5.32；N，4.48；实测元素含量(％)：C，90.24；H，5.33；N，4.47。上述结果证明获得产物为目标化合物。
实施例4：化合物63的制备
将实施例1中的1,4-二溴苯更换成2,7-二溴-9,9-二甲基芴。其他步骤同实施例1。质谱m/z：理论值：1214.53；实测值：1215.53。理论元素含量(％)C91H66N4：C，89.92；H，5.47；N，4.61；实测元素含量(％)：C，89.93；H，5.49；N，4.59。上述结果证明获得产物为目标化合物。
实施例5：化合物64的制备
将实施例1中的1,4-二溴苯更换成2,7-二溴-9,9’-螺二芴。其他步骤同实施例1。质谱m/z：理论值：1214.53；实测值：1215.53。理论元素含量(％)C91H66N4：C，89.92；H，5.47；N，4.61；实测元素含量(％)：C，89.93；H，5.49；N，4.59。上述结果证明获得产物为目标化合物。
实施例6：化合物65的制备
将实施例1中的1,4-二溴苯更换成2,2’-二溴-9,9’-螺二芴。其他步骤同实施例1。质谱m/z：理论值：1214.53；实测值：1215.53。理论元素含量(％)C91H66N4：C，89.92；H，5.47；N，4.61；实测元素含量(％)：C，89.94；H，5.45；N，4.59。上述结果证明获得产物为目标化合物。
实施例7：化合物69的制备
将实施例1中的1,4-二溴苯更换成2,7-二溴螺[芴-9,9'-氧杂蒽]。其他步骤同实施例1。质谱m/z：理论值：1353.54；实测值：1352.54。理论元素含量(％)C101H68N4O：C，89.62；H，5.06；N，4.14；O，1.18。实测元素含量(％)：C，89.63；H，5.08；N，4.16；O，1.19。上述结果证明获得产物为目标化合物。
实施例8：化合物70的制备
将实施例1中的1,4-二溴苯更换成2',7'-二溴螺[芴-9,9'-氧杂蒽]。其他步骤同实施例1。质谱m/z：理论值：1353.54；实测值：1352.54。理论元素含量(％)C101H68N4O：C，89.62；H，5.06；N，4.14；O，1.18。实测元素含量(％)：C，89.63；H，5.08；N，4.16；O，1.19。上述结果证明获得产物为目标化合物。
实施例9：化合物78的制备
将实施例1中的1,4-二溴苯更换成2,7-二溴二苯并呋喃。其他步骤同实施例1。质谱m/z：理论值：1188.48；实测值：1189.48。理论元素含量(％)C88H60N4O：C，88.86；H，5.08；N，4.71；O，1.35。实测元素含量(％)：C，88.89；H，5.07；N，4.71；O，1.34。上述结果证明获得产物为目标化合物。
实施例10：化合物79的制备
将实施例1中的1,4-二溴苯更换成2,7-二溴二苯并噻吩。其他步骤同实施例1。质谱m/z：理论值：1188.48；实测值：1189.48。理论元素含量(％)C88H60N4O：C，88.86；H，5.08；N，4.71；O，1.35。实测元素含量(％)：C，88.88；H，5.06；N，4.72；O，1.35。上述结果证明获得产物为目标化合物。
实施例11：化合物86的制备
将实施例1中的1,4-二溴苯更换成4,4'-二溴二苯醚。其他步骤同实施例1。质谱m/z：理论值：1190.49；实测值：1191.50。理论元素含量(％)C88H62N4O：C，88.71；H，5.25；N，4.70；O，1.34。实测元素含量(％)：C，88.72；H，5.26；N，4.69；O，1.34。上述结果证明获得产物为目标化合物。
实施例12：化合物92的制备
将实施例1中的1,4-二溴苯更换成4,4'-二溴二苯硫醚。其他步骤同实施例1。质谱m/z：理论值：1206.47；实测值：1207.47。理论元素含量(％)C88H60N4S：C，87.53；H，5.18；N，4.64；S，2.66。实测元素含量(％)：C，87.54；H，5.19；N，4.65；S，2.67。上述结果证明获得产物为目标化合物。
本发明实施例及上述所有实施例制备的有关化合物的数量是有限的，本专利中包括但没有一一列举实例的其他类似化合物，均可以采用具体实施方式中所述的化学反应制备得到。步骤一使用包含有未列举实例的取代基团R1,R2的伯胺，以及步骤三中包含有未列举实例的芳核Ar的二溴取代物，其中的R1,R2,Ar取代基团虽有所不同，但均是以芳香环状结构联接或稠合而形成的共轭结构，不会对本发明实施例中所采用的特定官能团反应造成任何影响，因此既可以起到与已列举实例类似的效果，发生相同类型的化学反应，也可以使制备得到的物质具有高玻璃化转变温度、高的稳定性及较强的载流子传输能力等类似的功能和优点。
对比实施例1
将ITO玻璃基板分别用去离子水、异丙醇、丙酮按顺序各超声清洗30min，反复清洗多次后用氮气吹干，转移到等离子清洗机中清洗5min，干燥并抽真空。首先在ITO玻璃基板上蒸镀一层5nm HATCN作为空穴注入层，蒸镀速率0.1nm/s。之后蒸镀有机空穴传输材料α-NPB，厚度30nm，蒸镀速率0.1nm/s再分别蒸镀发光层主体GH1：掺杂Ir(dppy)310％混合/30nm，蒸镀速率0.1nm/s。之后在发光层上分别蒸镀30nm TPBi作为电子传输层，蒸镀速率0.1nm/s和2.0nm LiF作为电子注入层，蒸镀速率0.1nm/s。最后，在电子注入层上真空蒸镀200nm金属阴极Al，蒸镀速率0.2nm/s。
Figure BDA0002211779350000221
应用实施例1
将对比应用实施例中的有机空穴传输材料α-NPB更换为实施例1的化合物1。
应用实施例2
将对比应用实施例中的有机空穴传输材料α-NPB更换为实施例2的化合物2。
应用实施例3
将对比应用实施例中的有机空穴传输材料α-NPB更换为实施例3的化合物3。
应用实施例4
将对比应用实施例中的有机空穴传输材料α-NPB更换为实施例4的化合物63。
应用实施例5
将对比应用实施例中的有机空穴传输材料α-NPB更换为实施例8的化合物79。
应用实施例6
将对比应用实施例中的有机空穴传输材料α-NPB更换为实施例11的化合物92。
本发明应用实施例1-6中使用的空穴传输材料的玻璃化转变温度，应用实例1-6及其对比实施例1制备的发光器件的发光特性测试结果如下表1所示。
表1实验结果
Figure BDA0002211779350000222
Figure BDA0002211779350000231
以上结果表明，本发明的新型空穴传输材料想对于常用的α-NPB，有着非常高的玻璃化转变温度，不易于结晶，成膜性优良。将之应用于有机电致发光器件中制备空穴传输层，该器件表现出更低的驱动电压和更高的电流效率，是一种优异的OLED空穴传输材料。
以上实施例进一步说明本发明的内容，但不应理解为对本发明的限制。在不背离本发明精神和实质的情况下，对本发明方法、步骤或条件所作的修改和替换，均属于本发明的范围。若未特别指明，实施例中所用的技术手段为本领域技术人员所熟知的常规手段。

Claims (6)

1.一种新型空穴传输材料，其特征在于，其分子结构通式如下所示：
Figure FDA0002211779340000011
其中，Ar选自取代或未取代的C6～C60芳基、取代或未取代的C10～C60稠环基、取代或未取代的C3～C60螺环基、取代或未取代的C3～C60杂环基；
R1、R2独立地选自取代或未取代的C6～C60芳基、取代或未取代的C10～C60稠环基。
2.根据权利要求1所述的新型空穴传输材料，特征在于，Ar选自取代或未取代的C6～C30芳基、取代或未取代的C10～C30稠环基、取代或未取代的C4～C30螺环基、取代或未取代的C4～C30杂环基；
R1、R2独立地选自取代或未取代的C6～C30芳基、取代或未取代的C10～C30稠环基。
3.根据权利要求2所述的新型空穴传输材料，其特征在于，Ar选自如下结构中的任意一种：
Figure FDA0002211779340000021
Figure FDA0002211779340000031
Figure FDA0002211779340000041
Figure FDA0002211779340000051
Figure FDA0002211779340000061
Figure FDA0002211779340000071
4.根据权利要求3所述的空穴传输材料，其特征在于，所述空穴传输材料选自如下化学结构中的任意一种：
Figure FDA0002211779340000081
Figure FDA0002211779340000091
Figure FDA0002211779340000101
Figure FDA0002211779340000111
Figure FDA0002211779340000121
Figure FDA0002211779340000131
Figure FDA0002211779340000141
Figure FDA0002211779340000151
Figure FDA0002211779340000161
Figure FDA0002211779340000171
5.一种有机电致发光器件，其特征在于，所述有机电致发光器件的有机功能层，包含权利要求1～4任一项所述的新型空穴传输材料。
6.根据权利要求5中所述的有机电致发光器件，其特征在于，所述有机功能层包括电荷传输层，电荷传输层包括空穴传输层和电子传输层；所述空穴传输层包含权利要求1～4任一项所述的新型空穴传输材料。
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