CN111995562A - 三蝶烯类d-a型热活化延迟荧光材料、电子器件及应用 - Google Patents

三蝶烯类d-a型热活化延迟荧光材料、电子器件及应用 Download PDF

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CN111995562A
CN111995562A CN202010962195.3A CN202010962195A CN111995562A CN 111995562 A CN111995562 A CN 111995562A CN 202010962195 A CN202010962195 A CN 202010962195A CN 111995562 A CN111995562 A CN 111995562A
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organic
triptycene
electronic device
delayed fluorescence
thermally activated
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占群
邹洋
杨楚罗
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Shenzhen University
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Abstract

本发明公开三蝶烯类D‑A型热活化延迟荧光材料、电子器件及应用，其中荧光材料具有以下结构通式中的一种：
Figure DDA0002680966530000011
X1选自不成键、单键、‑N(R1)‑、‑O‑、‑S‑、‑S＝O‑、‑SO2‑、‑C(R1R2)‑、‑S(R1R2)‑、‑P(R1)‑、‑P＝O(R1)‑；M1选自氢、氘、烯基、炔基、胺基、硝基、羰基、砜基、卤素、氰基、烷基、烷氧基、取代的C6～C60的芳香环基、未取代的C7～C60的芳香环基、C3～C60的芳杂环基；Y1选自氢、氘、烯基、炔基、胺基、硝基、羰基、砜基、卤素、氰基、烷基、烷氧基、取代的C6～C60的芳香环基、未取代的C7～C60的芳香环基、C3～C60的芳杂环基。

Description

三蝶烯类D-A型热活化延迟荧光材料、电子器件及应用
技术领域
本发明涉及有机电致发光材料技术领域，尤其涉及一种三蝶烯类D-A型热活化延迟荧光材料、电子器件及应用。
背景技术
近年来，有机发光二极管(OLED)发展为传统照明和显示器等材料的一种新兴替代品，它以可弯曲、功耗小以及色彩鲜艳等优良性能在发光材料领域迅速发展。
发光材料是有机发光二极管技术的核心，第一代传统荧光材料的能量利用效率(IQE)仅为25％，近几十年来，人们对拥有高能量利用率的Ir或Pt磷光发光材料进行了深入的研究，目前已达到100％的IQE。尽管磷光材料已经广泛应用于OLED技术领域，但是在包括成本高、蓝色发射的稳定性低以及在高电流密度下的强三重态湮灭等存在显著问题。热活化延迟荧光(TADF)是第三代发光材料，是基于热激活的三重态到单重态的反向系间窜越(RISC)机制，以及来自单重态的竞争性发光，可以达到100％的电致发光IQE。TADF材料的优点是纯有机材料，不需要昂贵的金属元素，如Pt和Ir等，且可达到100％的能量利用效率，这为发光分子和器件提供了新的设计思路。
对于可溶液加工及真空蒸镀的TADF材料，如何同时提高材料的稳定性、成膜性兼顾高的光致发光效率与快的反向系间窜越过程是实现高效器件的关键，也是目前亟需解决的问题。
发明内容
鉴于上述现有技术的不足，本发明的目的在于提供一种具有良好的稳定性、成膜性兼顾高的光致发光效率的三蝶烯类D-A型热活化延迟荧光材料，及采用该荧光材料的电子器件与应用。
本发明的技术方案如下：
本发明提供一种三蝶烯类D-A型热活化延迟荧光材料，其中，具有以下结构通式中的一种：
Figure BDA0002680966520000021
X1选自不成键、单键、-N(R1)-、-O-、-S-、-S＝O-、-SO2-、-C(R1R2)-、-S(R1R2)-、-P(R1)-、-P＝O(R1)-中的任意一种；其中R1、R2各自独立地选自氢、氘、烯基、炔基、胺基、硝基、羰基、砜基、卤素、氰基、烷基、烷氧基、取代的C6～C60的芳香环基、未取代的C7～C60的芳香环基、取代或未取代的C3～C60的芳杂环基中的一种；
M1选自氢、氘、烯基、炔基、胺基、硝基、羰基、砜基、卤素、氰基、烷基、烷氧基、取代的C6～C60的芳香环基、未取代的C7～C60的芳香环基、取代或未取代的C3～C60的芳杂环基中的一种；
Y1选自氢、氘、烯基、炔基、胺基、硝基、羰基、砜基、卤素、氰基、烷基、烷氧基、取代的C6～C60的芳香环基、未取代的C7～C60的芳香环基、取代或未取代的C3～C60的芳杂环基中的一种；
其中，X1、Y1、M1均能够相互以共价键方式相连成环(即可以成环，也可以不成环)。
本发明提供了一种三蝶烯类D-A型分子，通过在三蝶烯的不同位点引入给体和受体分子来改变材料的整体结构，通过调控分子结构，实现高纯度、多颜色发光。由于此类分子包含三蝶烯立体三维的结构，使这类分子具有三蝶烯的优点，如：溶解性好，热稳定好，分子结构易于调控，分子可精确的重复合成等，改善传统D-A型热活化延迟荧光分子由于在固态下会发生分子间聚集，导致降低OLED器件效率的问题；同时又由于包含传统D-A分子，使这类分子能精确调控发光颜色及其发光效率。
进一步地，所述热活化延迟荧光材料具有以下结构中的一种：
Figure BDA0002680966520000031
Figure BDA0002680966520000041
更进一步地，上述M1选自以下结构中的一种：
Figure BDA0002680966520000042
Figure BDA0002680966520000051
本发明中，通过改变连接位点和连接基团，可以得到大约648种热活化延迟荧光材料。进一步地，所述热活化延迟荧光材料具有以下结构中的一种：
Figure BDA0002680966520000052
Figure BDA0002680966520000061
Figure BDA0002680966520000071
Figure BDA0002680966520000081
Figure BDA0002680966520000091
Figure BDA0002680966520000101
Figure BDA0002680966520000111
本发明提供一种电子器件，其中，包括本发明所述的三蝶烯类D-A型热活化延迟荧光材料。
进一步地，所述电子器件为有机电致发光器件、有机发光电池、有机场效应管、有机发光场效应管、有机激光器、有机传感器、有机光伏电池、有机自旋电子器件中的一种，但不限于此。
更进一步地，所述电子器件为有机电致发光器件，所述有机电致发光器件包括功能层，所述功能层由质量百分含量为0.1～99.9％的三蝶烯类D-A型热活化延迟荧光材料和质量百分含量为0.1～99.9％的有机功能材料组成；
其中所述有机功能材料选自空穴注入材料、空穴传输材料、空穴阻挡材料、电子注入材料、电子传输材料、电子阻挡材料、激子阻隔材料、荧光发光材料、磷光发光材料、主体材料及有机染料中的一种。
更进一步地，所述电子器件为有机电致发光器件，所述有机电致发光器件包括发光层，所述发光层包括本发明所述的三蝶烯类D-A型热活化延迟荧光材料。
本发明提供一种所述的电子器件在电子设备中的应用。
本发明还提供了一种制备上述三蝶烯D-A型热活化延迟荧光材料的方法，该方法将三蝶烯与吖啶、吩噁嗪以及咔唑等电子给体中的至少一种进行相连，形成上述结构式中的一种结构。
本发明具有以下有益效果：
本发明通过在三蝶烯的邻位或对位引入给电子基团，再接入不同的吸电子基团改变材料的整体结构，实现高纯度、多种颜色发光，改善目前热活化延迟荧光材料性能不佳问题；
本发明材料结构新颖，可通过Buchwald-Hartwig反应直接连上不同的电子受体；
本发明材料可在有机电致发光器件中作为发光层材料，由于引入三维立体结构且反应位点多样的三蝶烯，因此具有分子结构易于调控，分子可精确的重复合成等优点，改善传统D-A型热活化延迟荧光分子由于在固态下会发生分子间聚集，导致降低OLED器件效率的问题，由此可将该材料应用于不掺杂主体材料的OLED器件(通常掺杂主体材料主要是抑制客体材料的聚集诱导发光猝灭效应)；
本发明材料可通过连接不同的给体单元来调节结构，以实现多种波长的发射光，该材料作为发光层客体材料应用于溶液加工和真空蒸镀的电致发光器件中具有良好的综合性能；
由于在外电压作用下，不同的给电子基团可以较好地与酮类、氰基类、砜类等不同的吸电子受体结合，且给体和受体单元间通过苯环连接，可实现一定的分子扭曲，从而较好地分离最高占据轨道(HOMO)和最低未占据轨道(LUMO)，较小的HOMO和LUMO重叠可以减小单线态和三线态之间的能级差(ΔEST)，该材料的ΔEST小于或等于0.1eV，足够小的ΔEST可以实现TADF性质。且较小的ΔEST使反向系间窜越过程的效率更高，因此应用该类材料的OLED器件可实现高的发光效率，同时有效降低起亮电压；
引入三维立体结构的三蝶烯后，分子的溶解性显著提高，以此将其应用于溶液加工型非掺杂器件，简化器件结构，解决大面积柔性OLED的技术缺陷问题，而且上述化合物通过拓展分子共轭提高分子刚性，可以最小化分子激发态中的非辐射跃迁过程，并且高的分子刚性对于提高量子产率至关重要；
上述三蝶烯类化合物无玻璃化转变温度Tg，分解温度Td大于或等于400℃，使得材料具有良好的热稳定性，材料的应用范围更广。
具体实施方式
本发明提供一种三蝶烯类D-A型热活化延迟荧光材料、电子器件及应用，为使本发明的目的、技术方案及效果更加清楚、明确，以下对本发明进一步详细说明。应当理解，此处所描述的具体实施例仅仅用以解释本发明，并不用于限定本发明。
下面通过具体的实施例对本发明作进一步地说明。
实施例1
本实施例中的热活化延迟荧光材料TTC-DMAC-TRZ(化合物60)和TTC-DMAC-PM(化合物61)的结构式分别如下：
Figure BDA0002680966520000131
上述热活化延迟荧光材料的具体合成过程如下：
Figure BDA0002680966520000132
化合物2的制备：选取100mL两口烧瓶，在氩气保护下加入1-氨基三蝶烯(2.36g，10mmol)，邻氨基苯甲酸甲酯(3.62g，24mmol)，醋酸钯(224.5mg，1mmol)，碳酸铯(13.0g，40mmol)，三叔丁基磷四氟硼酸盐(754.3mg，2.6mmol)和30mL甲苯，120℃下反应12小时。冷却至室温后，经硅藻土过滤掉无机盐，硅胶柱层析分离，得白色固体2.86g，产率76％。MS(EI):m/z 430.1[M+]。
Figure BDA0002680966520000141
TTC-DMAC的制备：将化合物2(1.30g，3.4mmol)溶于20mL无水THF中，并在氩气下冷却至0℃。然后将甲基溴化镁(10mL，3M，13.4mmol)滴加到该混合物中，并在70℃下回流3小时。将反应混合物逐渐温热至室温，用氯化铵溶液(2M)淬灭，并用DCM萃取三次。有机相用无水Na2SO4干燥。过滤并减压浓缩后，将粗制二醇中间体在氩气下溶于10mL无水DCM中，并逐滴加入10mL三氟化硼乙醚。将混合物在室温下在氩气下进一步搅拌过夜。然后将反应混合物用NaOH(2M)中和，并用DCM萃取三次。合并的有机相用无水Na2SO4干燥并在减压下浓缩。粗产物通过硅胶柱色谱法纯化，使用DCM/石油醚(v/v＝1/1)作为洗脱剂，得到白色粉末状产物TTC-DMAC。产率：50％。MS(ESI):m/z 386.1904[M+]。
Figure BDA0002680966520000142
化合物60的制备：将TTC-DMAC(0.35g，0.9mmol)，2-(4-溴苯基)-4,6-二苯基-1,3,5-三嗪(0.42g，1.1mmol)，醋酸钯(0.01g，0.05mmol)，叔丁醇钠(0.17g，1.8mmol)，三叔丁基磷四氟硼酸盐(0.05g，0.18mmol)和10mL无水甲苯搅拌并在氩气下回流24小时。冷却至室温后，将反应混合物通过硅藻土垫过滤，并用二氯甲烷洗涤。将有机相在减压下浓缩。残余物通过硅胶柱色谱纯化，使用二氯甲烷/石油醚(v/v＝1/3)作为洗脱剂，得到产物，为绿色固体。产率72％。MS(ESI):m/z 693.3026[M+]。
Figure BDA0002680966520000151
化合物61的制备：利用与化合物60相同的合成方式来制备化合物61，不同之处在于使用2-(4-溴苯基)-4，6-二苯基嘧啶代替化合物60合成过程中的2-(4-溴苯基)-4，6-二苯基-1，3，5-三嗪，得绿色粉末，产率70％。MS(ESI):m/z 692.3082[M+]。
实施例2
本实施例的TTC-PXZ的制备，反应式如下:
Figure BDA0002680966520000152
化合物2的制备：选取250mL两口烧瓶，在氩气保护下加入2-羟基三蝶烯(1.60g，5.9mmol)和30mL甲苯，缓慢加入N-溴代琥珀酰亚胺(1.05g，5.9mmol)，0℃下反应2小时。反应完后硅胶柱层析分离，得白色固体1.80g，产率90％。MS(EI):m/z 348.0[M+]。
化合物3的制备：选取100mL两口烧瓶，在氩气保护下加入化合物2(0.80g，2.3mmol)，邻氟硝基苯(0.39g，2.7mmol)，碳酸钾(0.63g，4.6mmol)和30mL N,N-二甲基甲酰胺(DMF)，100℃下反应12小时。冷却至室温后，倒入水中过滤得到固体，硅胶柱层析分离，得白色固体0.86g，产率78％。MS(EI):m/z 469.1[M+]。
化合物4的制备:选取250mL两口烧瓶，在氩气保护下加入化合物3(3.30g，7.0mmol)，二水合氯化亚锡(6.33g，28.0mmol)和65mL乙醇，70℃下反应12小时。冷却至室温后，旋干用硅胶柱层析分离，得白色固体2.50g，产率81％。MS(EI):m/z 439.1[M+]。
TTC-PXZ的制备：将化合物4(2.0g,4.0mmol)在氩气下溶于20mL无水DCM中，并逐滴加入10mL三氟化硼乙醚。将混合物在室温下在氩气下进一步搅拌过夜。然后将反应混合物用NaOH(2M)中和，并用DCM萃取三次。合并的有机相用无水Na2SO4干燥并在减压下浓缩。粗产物通过硅胶柱色谱法纯化，得到白色粉末状产物。产率：60％。MS(ESI):m/z 359.1[M+]。
化合物12的制备，反应式如下:
Figure BDA0002680966520000161
利用化合物60类似的合成方式来制备化合物12，不同之处在于使用2-羟基三蝶烯代替实施例1中的2-氨基三蝶烯，使用邻氟硝基苯代替实施例1中的邻氨基苯甲酸甲酯，得白色粉末，产率40％。MS(EI):m/z 359.1[M+]。
选取50mL两口烧瓶，在氩气保护下加入TTC-PXZ(438mg，1mmol)，2-(4-溴苯基)-4，6-二苯基-1，3，5-三嗪(500.2mg，1.2mmol)，醋酸钯(22.4mg，0.1mmol)，叔丁醇钠(384mg，4mmol)，三叔丁基磷四氟硼酸盐(75.4mg，0.26mmol)和10mL甲苯，120℃下反应12小时。冷却至室温后，经硅藻土过滤掉无机盐，硅胶柱层析分离，得白色粉末，产率71％。MS(EI):m/z666.24[M+]。
化合物13的制备，反应式如下:
Figure BDA0002680966520000171
利用与化合物12相同的合成方式来制备化合物13，不同之处在于使用2-(4-溴苯基)-4，6-二苯基嘧啶代替化合物12合成过程中的2-(4-溴苯基)-4，6-二苯基-1，3，5-三嗪，得黄绿色粉末，产率60％。MS(EI):m/z665.24[M+]。
测试：
测定化合物12、化合物13、化合物60和化合物61，化合物DMAC-TRZ[10-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9,10-dihydroacridine，即10-(4-(4,6-二苯基-1,3,5-三唑-2-基)苯基)-9,9-二甲基-9,10-二氢吖啶]的玻璃化转变温度、分解温度。化合物的能级利用含时密度泛函理论(TD-DFT)通过Gaussian 09软件模拟，运用函数B3LYP方法计算。表1列出了化合物12、化合物13、化合物60、化合物61和DMAC-TRZ的玻璃化转变温度、分解温度以及理论计算所得能级数据。
表1、化合物12-13、化合物61-62与DMAC-TRZ的玻璃化转变温度、分解温度及能级
Figure BDA0002680966520000181
由表1可以看出，化合物12-13和化合物60-61的HOMO和LUMO能级差较小，表明化合物12-13和化合物60-61的给受体之间能级重叠很小，符合热活化延迟荧光分子的特点；同时它们的玻璃化转变温度均在110℃以上，热分解温度均在340℃以上，均高于DMAC-TRZ，说明化合物12-13和化合物60-61的热稳定性均优于DMAC-TRZ。同时，化合物12-13和化合物60-61的ΔEST均很小，说明该化合物的材料的发光效率较高。
进一步的，实施例1-2得到的化合物12-13和化合物60-61可以用于电致发光器件中的发光层，以溶液加工法制作四组器件。
器件具体结构为：
器件A1
ITO/PEDOT:PSS/TTC-DMAC-TRZ/DPEPO/TmPyPB/Liq/Al
器件A2
ITO/PEDOT:PSS/mCP:TTC-DMAC-TRZ(质量比为80:20)/DPEPO/TmPyPB/Liq/Al
器件A3
ITO/PEDOT:PSS/TTC-DMAC-PM/DPEPO/TmPyPB/Liq/Al
器件A4
ITO/PEDOT:PSS/mCP:TTC-DMAC-PM(质量比为80:20)/DPEPO/TmPyPB/Liq/Al
其中PEDOT、Liq、mCP、DPEPO和TmPyPB的结构式分别如下：
Figure BDA0002680966520000191
制造OLED器件的具体步骤为：将镀有氧化铟锡(ITO)的玻璃基板依次用去离子水、丙酮、异丙醇超声洗涤30分钟，紫外线臭氧处理15分钟后，将玻璃基板传送至溶液加工室中；依次旋涂各有机层及阴极铝层；将该器件从溶液加工室传送至手套箱中进行封装。
对以上电致发光器件进行性能测试，结果如下表2所示：
表2、器件性能数据
Figure BDA0002680966520000192
由器件性能数据可得出，实施例实现了如下技术效果：由于引入三维立体结构且反应位点多样的三蝶烯，具有分子结构易于调控，分子可精确的重复合成等优点，改善传统D-A型热活化延迟荧光分子由于在固态下会发生分子间聚集，导致降低OLED器件效率的问题，而且通过引入三蝶烯提高分子刚性，具有非常好的热力学稳定性以及溶解性；上述热激活延迟荧光材料可作为OLED中的热激活延迟荧光(TADF)发光层材料，应用于不掺杂主体材料的溶液加工型OLED器件，降低材料制备成本，获得了高的器件效率和良好的稳定性。
本发明中所涉及的其他衍生物的制备方法与相应的实施例方法相似，只是链接的给体和受体的种类数量不同，通过Buchwald-Hartwig偶联均可制得。
应当理解的是，本发明的应用不限于上述的举例，对本领域普通技术人员来说，可以根据上述说明加以改进或变换，所有这些改进和变换都应属于本发明所附权利要求的保护范围。

Claims (9)

1.一种三蝶烯类D-A型热活化延迟荧光材料，其特征在于，具有以下结构通式中的一种：
Figure FDA0002680966510000011
X1选自不成键、单键、-N(R1)-、-O-、-S-、-S＝O-、-SO2-、-C(R1R2)-、-S(R1R2)-、-P(R1)-、-P＝O(R1)-中的任意一种；其中R1、R2各自独立地选自氢、氘、烯基、炔基、胺基、硝基、羰基、砜基、卤素、氰基、烷基、烷氧基、取代的C6～C60的芳香环基、未取代的C7～C60的芳香环基、取代或未取代的C3～C60的芳杂环基中的一种；
M1选自氢、氘、烯基、炔基、胺基、硝基、羰基、砜基、卤素、氰基、烷基、烷氧基、取代的C6～C60的芳香环基、未取代的C7～C60的芳香环基、取代或未取代的C3～C60的芳杂环基中的一种；
Y1选自氢、氘、烯基、炔基、胺基、硝基、羰基、砜基、卤素、氰基、烷基、烷氧基、取代的C6～C60的芳香环基、未取代的C7～C60的芳香环基、取代或未取代的C3～C60的芳杂环基中的一种；
其中，X1、Y1、M1均能够相互以共价键方式相连成环。
2.根据权利要求1所述的三蝶烯类D-A型热活化延迟荧光材料，其特征在于，所述热活化延迟荧光材料具有以下结构中的一种：
Figure FDA0002680966510000012
Figure FDA0002680966510000021
3.根据权利要求2所述的三蝶烯类D-A型热活化延迟荧光材料，其特征在于，所述M1选自以下结构中的一种：
Figure FDA0002680966510000022
Figure FDA0002680966510000031
4.根据权利要求1所述的三蝶烯类D-A型热活化延迟荧光材料，其特征在于，所述热活化延迟荧光材料具有以下结构中的一种：
Figure FDA0002680966510000032
Figure FDA0002680966510000041
Figure FDA0002680966510000051
Figure FDA0002680966510000061
Figure FDA0002680966510000071
Figure FDA0002680966510000081
Figure FDA0002680966510000091
5.一种电子器件，其特征在于，包括权利要求1-4任一项所述的三蝶烯类D-A型热活化延迟荧光材料。
6.根据权利要求5所述的电子器件，其特征在于，所述电子器件为有机电致发光器件、有机发光电池、有机场效应管、有机发光场效应管、有机激光器、有机传感器、有机光伏电池、有机自旋电子器件中的一种。
7.根据权利要求6所述的电子器件，其特征在于，所述电子器件为有机电致发光器件，所述有机电致发光器件包括功能层，所述功能层由质量百分含量为0.1～99.9％的三蝶烯类D-A型热活化延迟荧光材料和质量百分含量为0.1～99.9％的有机功能材料组成；
所述有机功能材料选自空穴注入材料、空穴传输材料、空穴阻挡材料、电子注入材料、电子传输材料、电子阻挡材料、激子阻隔材料、荧光发光材料、磷光发光材料、主体材料及有机染料中的一种。
8.根据权利要求5所述的电子器件，其特征在于，所述电子器件为有机电致发光器件，所述有机电致发光器件包括发光层，所述发光层包括所述三蝶烯类D-A型热活化延迟荧光材料。
9.权利要求5～8任一项所述的电子器件在电子设备中的应用。
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