CN105601557B - 含蒽类化合物、其制备方法及其应用、有机发光器件 - Google Patents

含蒽类化合物、其制备方法及其应用、有机发光器件 Download PDF

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CN105601557B
CN105601557B CN201610090045.1A CN201610090045A CN105601557B CN 105601557 B CN105601557 B CN 105601557B CN 201610090045 A CN201610090045 A CN 201610090045A CN 105601557 B CN105601557 B CN 105601557B
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anthracene
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李彦松
马晓宇
王辉
李娜
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

本发明提供了一种用于荧光主体材料，空穴注入材料或者空穴传输材料蒽类化合物及其应用,和包含有该有机发光化合物的有机发光器件。所述蒽类化合物的分子结构式为：

Description

含蒽类化合物、其制备方法及其应用、有机发光器件
本申请是中国专利申请No.201310666464.1的分案申请，原申请的申请日为2013.12.10，申请号为201310666464.1，发明名称为含蒽类化合物、其制备方法及其应用、有机发光器件。
技术领域
本发明涉及有机光电材料领域，尤其涉及一类含蒽类化合物、制备方法及其应用、有机发光器件。
背景技术
有机发光器件的基本结构包括两个相对的电极，即阴极和阳极，以及包含有机材料层。在阳极和阴极之间施加电压，空穴就从阳极通过空穴传输层注入到发光层中。同时，电子从阴极通过电子传输层注入到发光层中。在发光层区域，载流子重排形成激子。激发态激子转变到基态，引起发光层分子发光，发光因此形成。发光材料根据发光机理分为两组：一组由利用单线态激子的荧光材料组成，另一组由利用三线态激子的磷光物质组成。
有机电致发光现象是电流通过特定有机分子的内部作用而转化成可见光线。在有机发光器件中，通常包含阴极、阳极和阴极与阳极之间的有机材料层。就这一点而言，有机材料层可包含几个由不同材料形成的层的多层结构以提高所形成的OLED的效率和稳定性。例如，有机材料层可包含空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等。
发光材料可发出蓝色、绿色、红色和黄色等几种光。为提高发光层的发光效率，可在发光层中加入其他具有更高量子产量的发光材料。已知激发子具有将其能量转移给重新组合部位附近的材料中具有更小带隙的材料的倾向。因此，掺杂剂选自比主材料具有更高的量子产量和更小的带隙(更大的波长)的材料；否则，激发子的能量将转移至具有更低量子产量的主材料，并因此产生弱的发射或者不发射。
为了有效发挥有机电致发光器件的优秀特征，可以采用稳定有效率的材料作为OLED器件内的有机材料层，即空穴注入层、空穴传输层、发光层，电子传输层、电子注入层等。但是至今没有理想的稳定高效率的有机发光材料用于有机材料层，所以新材料的研究势在必行。
发明内容
鉴于上述现有技术的不足，本发明在蒽上引入高效率及热稳定性好的芳香族，提高了材料的发光效率及稳定性。本发明的目的在于提供一类含蒽类化合物、制备方法及其应用，旨在提供一种新的高效的有机电致发光材料。
本发明的技术方案如下：
一类含蒽类化合物，其特征在于，所述蒽类化合物的分子通式为：
其中，R基团选自芳香基、芳族杂环基或取代的芳族杂环基，所述芳香基、芳族杂环基或取代的芳族杂环基由6～19个碳原子构成；或者R基团为4-吡啶基。
较优的，R基团选自苯基、4-联苯基、2-萘基、8-喹啉基、9-菲基、4-吡啶基、非那烯基、4-(4-吡啶基)-苯基、9,9-二甲基芴基、3,5-二苯基苯基、9-蒽基、2-苯并噻唑基。
具体的，所述的含蒽类化合物，其中，所述含蒽类化合物至少为
中的一种；或者为
本发明还提供了一种上述含蒽类化合物的制备方法，包括如下步骤：
步骤S1：对反应容器进行脱气，向反应容器中加入蒽衍生物的溴化物、含R基团取代的硼酸、碳酸钾和甲苯；
步骤S2：然后加入催化剂，升高反应温度至70℃并回流，充分反应；
步骤S3：经萃取、洗涤、干燥、柱层析纯化得到所述蒽类化合物。
较优的，所述的制备方法，所述步骤S1中的蒽衍生物的溴化物由9,10-蒽醌制备而成。
较优的，所述制备方法，所述步骤S1中的蒽衍生物的溴化物的制备方法，包括如下步骤：
步骤N1：对反应容器进行脱气，向反应容器中加入2-溴-6-苯蒽、四氢呋喃；
步骤N2：对反应体系降温，加入n-BuLi；
步骤N3：加入所述9,10-蒽醌；
步骤N4：升高反应温度至室温，充分反应后加NH4Cl终止。
步骤N5：经萃取、洗涤、干燥、柱层析纯化得到蒽类衍生物的醇类化合物。
步骤N6：加入碘化钾、磷酸二氢钠、冰醋酸进行脱水反应得到蒽类衍生物。
步骤N7：加入溴水溴化后得到步骤S1中蒽类衍生物的溴化物。
一种所述含蒽类化合物的应用，所述含蒽类化合物在所述有机电致发光器件中用作荧光主体材料、空穴注入材料或者空穴传输材料。
较优的，所述的含蒽类化合物在所述有机电致发光器件中用作荧光绿色主体材料。
本方案还提供了一种所述含蒽类化合物制成的有机发光器件，其包括第一电极、第二电极以及置于所述第一电极、所述第二电极之间的一个或多个有机化合物层，至少一个所述有机化合物层包含所述含蒽类化合物。
本发明提供的一种含蒽类化合物、制备方法及其应用，采含蒽类化合物具有高的发光效率，高的发光效率表明该化合物可作为发光材料或发光主体材料，尤其是可以作为荧光主体材料，含蒽类化合物还具有高的玻璃化温度并且不易结晶，用于有机电致发光器件中表现出高效率、高亮度、长寿命且更好的电荷传输能力，具有制造成本较低的优点，并且延长了有机电致发光器件的寿命，降低了有机电致发光器件的制造成本。
具体实施方式
本发明提供了一类含蒽类化合物、制备方法及其应用，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。
本发明提供了一类含蒽类化合物，所述蒽类化合物的分子通式为：
其中，R基团选自碳原子数为6-19个原子构成的芳香基、芳族杂环基或取代的芳族杂环基系列基团；或者R基团为4-吡啶基。
较优的，其中，R基团代表由6-50个原子构成的苯基、联苯基、萘基、喹啉基、菲基、吡啶基、非那烯基、9,9-二甲基芴基、三联苯基、蒽基、芳香氨基、咔唑基、苯并噻唑基、噻吩基、芳香氨基、芳族杂环基、取代的芳族杂环基或苯胺系列基团。其具体的表现形式至少为表1中标号1-12中的一种。
表1
本发明提供的含蒽类化合物的制备方法，包括如下步骤：
步骤S1：对反应容器进行脱气，向反应容器中加入蒽衍生物的溴化物、含R基团取代的硼酸、碳酸钾和甲苯；
步骤S2：然后加入催化剂，升高反应温度至70℃并回流，充分反应；
步骤S3：经萃取、洗涤、干燥、柱层析纯化得到所述蒽类化合物。
较优的，所述步骤S1中的蒽衍生物的溴化物由9,10-蒽醌制备而成。
具体的，步骤S1中的蒽衍生物的溴化物，是以2-溴-6-苯蒽、9,10-蒽醌为原料，经过醇化、脱水、溴化等多步反应得到的，其包括如下步骤：
步骤N1：对反应容器进行脱气，向反应容器中加入2-溴-6-苯蒽、四氢呋喃；
步骤N2：对反应体系降温，加入n-BuLi；
步骤N3：加入所述9,10-蒽醌；
步骤N4：升高反应温度至室温，充分反应后加NH4Cl终止；
步骤N5：经萃取、洗涤、干燥、柱层析纯化得到蒽类衍生物的醇类化合物；
步骤N6：加入碘化钾、磷酸二氢钠、冰醋酸进行脱水反应得到蒽类衍生物中间体；
步骤N7：加入溴水溴化后得到步骤S1中蒽类衍生物的溴化物。
为了更详尽的说明本发明中的制备方法，以下以表1中标号为1、8、11的含蒽类化合物 为例进行描述。其具体的反应方程式如下式所示。
化合物[1-1]的合成方法：
1、在氮气保护下，向反应容器中加入2-溴-6-苯蒽(83.31g,0.25mol)、THF(四氢呋喃)250mL，常温搅拌10分钟。
2、原料完全溶解后降温至-72℃，慢慢滴加n-BuLi 100mL。
3、低温反应3h后，加入9,10-蒽醌(21.02g,0.1mol)的THF溶液150mL。
4、然后慢慢升温至常温，搅拌24h。加入蒸馏水500mL，NH4Cl过饱和溶液500mL和二氯甲烷500mL搅拌2h。
5、萃取有机层，减压干燥。此固体加1L丙酮搅拌1h后，过滤，减压浓缩有机溶剂，得出淡褐色固体[1-3]化合物48.89g，产率68％。
6、将[1-3]化合物，碘化钾(11.62g,0.07mol),磷酸二氢钠(16.80g,0.14mol),冰醋酸200mL加入到反应容器中，回流搅拌反应20h。反应结束后冷却至室温，加入500mL蒸馏水搅拌后减压抽滤。固体加入500mL NaHCO3过饱和溶液中，搅拌30min后减压抽滤，用过饱和的500mL NaCl和1L蒸馏水洗涤，减压抽滤。得到深黄色固体，室温下真空干燥后得出[1-2]化合物40.63g，产率85％。
7、氮气保护下向2L烧瓶中加入化合物[1-2](40.63g,0.06mol),加入1L四氯化碳作溶剂，加溴室温反应半小时。用TLC(薄膜色谱)方法确认反应结束后，减压过滤，用500mL丙酮搅拌。减压过滤后得到淡绿色固体目的化合物[1-1]49.72g，产率83％。
具体的，标号为1的化合物合成方法：
1、在氮气保护下，向2L反应釜中加入化合物[1-1](49.72g,0.05mol)，苯硼酸(27.43g,0.225mol)，K2CO3(34.55g,0.25mol)，甲苯500mL搅拌。
2、温度升高到70℃时，加入催化剂Pd(PPh3)4(1.16g,0.001mol),加入蒸馏水75mL搅拌11h。充分反应后，加100mL水结束反应。
3、减压过滤得到目标化合物粗产品，用蒸馏水洗涤三次，然后用丙酮，甲苯，THF重结晶得到固体再升华精制处理，甲苯重结晶，得到淡黄色固体目标化合物[1]36.53g，产率74％。
标号为8的化合物合成方法：
1、在氮气保护下，向2L反应釜中加入化合物[1-1](49.72g,0.05mol)，4-(4-吡啶基)苯基硼酸(44.78g,0.225mol)，K2CO3(34.55g,0.25mol)，甲苯500mL搅拌。
2、温度升高到70℃时，加入催化剂Pd(PPh3)4(1.16g,0.001mol),加入蒸馏水75mL搅拌11h。充分反应后，加100mL水结束反应。
3、减压过滤得到目标化合物粗产品，用蒸馏水洗涤三次，然后用丙酮，甲苯，THF重结晶得到固体再升华精制处理，甲苯重结晶，得到淡黄色固体目标化合物[8]50.52g，产率78％。
标号为11的化合物合成方法：
1、在氮气保护下，向2L反应釜中加入化合物[1-1](49.72g,0.05mol)，9-蒽硼酸(49.96g,0.225mol)，K2CO3(34.55g,0.25mol)，甲苯500mL搅拌。
2、温度升高到70℃时，加入催化剂Pd(PPh3)4(1.16g,0.001mol),加入蒸馏水75mL搅拌11h。充分反应后，加100mL水结束反应。
3、减压过滤得到目标化合物粗产品，用蒸馏水洗涤三次，然后用丙酮，甲苯，THF重结晶得到固体再升华精制处理，甲苯重结晶，得到淡黄色固体目标化合物[11]52.71g，产率76％。
其中表1中标号1～12含蒽类化合物的制备过程基本相同，在此不再一一赘述，仅将其具体结果列于表2中。并且在制备本发明含蒽类化合物过程中，添加各个物质的量，可以根据上述实施例中各个物质的比例进行确定，本发明重点是描述工艺过程，对添加各个物质的量不再作一一阐述。
表2
本发明实施例还提供了一种有机发光器件，其包括第一电极、第二电极以及置于所述第一电极、所述第二电极之间的一个或多个有机化合物层，至少一个所述有机化合物层包含所述含蒽类化合物。
本发明实施例还提供了一种所述含蒽类化合物的应用，所述含蒽类化合物在所述有机电致发光器件中用作荧光主体材料、空穴注入材料或者空穴传输材料。优选地，在本发明实施例中，提供了一种以上述含蒽类化合物作为荧光绿色主体材料的应用。
以下内容以应用为荧光绿色主体材料为例，进一介绍本发明实施例提供的含蒽类化合物。
对比样品
下面化合物a用作荧光绿色主体材料，c作为荧光绿色掺杂材料，2-TNATA作为空穴注入层材料，α-NPD(N,N’-二萘基-N,N’-二苯基联苯胺)作为空穴传输层材料使用，制作下面结构的有机发光器件。
ITO/2-TNATA(80nm)/α-NPD(30nm)/化合物a+化合物c(30nm)/Alq3(30nm)/LiF(0.5nm)/Al(60nm)。
阳极是15Ω/cm2 ITO玻璃基板，按照50mm×50mm×0.7mm大小切割，然后在丙酮、异丙醇和纯净水中超声波15分钟清洗，30分钟UV臭氧洗净使用。在基板上面真空镀膜2-TANATA形成80nm厚度的空穴注入层。在空穴注入层上真空镀膜α-NPD 30nm厚度形成空穴传输层。在空穴传输层上真空镀膜化合物a及化合物c(3％涂料)，形成30nm厚度的发光层。之后，在发光层上真空镀膜Alq3 30nm厚度形成电子传输层。在电子传输层上面，在依次真空镀膜LiF 0.5nm(电子注入层)和Al 60nm(阴极)。
比较实施例1～12：
将对比样品1中的荧光绿色主体材料采用表1中表示1-12的衍生物替代原化合物a，其余的处理工艺以及条件均相同，制得有机发光器件。
测量对比样品1以及实施例2所得有机发光器件的发光性能，采用源测量单元Keithley SMU235,评价发光亮度，发光效率，发光颜色。对比样品1以及实施例2进行同样的试验，结果列于表3中。
表3
如表3所示，上述样品都在512-524nm波长范围内显示发光颜色为绿色。样品1-12与对比样品1相比有显著提高的发光特性。
虽然本发明用示范性实施方案进行了特别的描述，但应该理解在不偏离下列权利要求所限定的本发明的精神与范围的情况下，本领域普通技术人员可对其进行各种形式和细节上的改变。

Claims (7)

1.一种含蒽类化合物，其特征在于，所述含蒽类化合物的分子结构式为：
2.一种如权利要求1所述的含蒽类化合物的制备方法，其特征在于，包括如下步骤：
步骤S1：对反应容器进行脱气，向反应容器中加入蒽衍生物的溴化物、4-吡啶硼酸、碳酸钾和甲苯，其中所述蒽衍生物的溴化物的结构式如式[1-1]所示：
步骤S2：升高反应温度至70℃，然后加入催化剂并回流，充分反应；
步骤S3：经过滤、洗涤、重结晶得到所述蒽类化合物。
3.根据权利要求2所述的制备方法，其特征在于，所述步骤S1中的蒽衍生物的溴化物由2-溴-6-苯蒽和9,10-蒽醌制备而成。
4.根据权利要求2所述的制备方法，其特征在于，所述步骤S1中的蒽衍生物的溴化物的制备方法，包括如下步骤：
步骤N1：对反应容器进行脱气，向反应容器中加入2-溴-6-苯蒽、四氢呋喃；
步骤N2：对反应体系降温，加入n-BuLi；
步骤N3：加入所述9,10-蒽醌；
步骤N4：升高反应温度至室温，充分反应后加NH4Cl终止；
步骤N5：经萃取、洗涤、干燥、柱层析纯化得到蒽类衍生物的醇类化合物，其中所述蒽类衍生物的醇类化合物的结构式如式[1-3]所示：
步骤N6：加入碘化钾、磷酸二氢钠、冰醋酸进行脱水反应得到蒽类衍生物中间体，其中所述蒽类衍生物中间体的结构式如[1-2]所示：
步骤N7：加入溴水溴化后得到步骤S1中蒽衍生物的溴化物。
5.根据权利要求1所述的含蒽类化合物在有机电致发光器件中的应用，其特征在于，所述的含蒽类化合物在所述有机电致发光器件中用作荧光主体材料、空穴注入材料或者空穴传输材料。
6.根据权利要求5所述的应用，其特征在于，所述的含蒽类化合物在所述有机电致发光器件中用作荧光绿色主体材料。
7.一种有机发光器件，包括第一电极、第二电极和置于所述两电极之间的一个或多个有机化合物层，其特征在于，至少一个有机化合物层包含至少一种如权利要求1所述含蒽类化合物。
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