CN111620855B - 一种含苯并氧杂蒽类化合物材料及其应用 - Google Patents

一种含苯并氧杂蒽类化合物材料及其应用 Download PDF

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CN111620855B
CN111620855B CN202010536642.9A CN202010536642A CN111620855B CN 111620855 B CN111620855 B CN 111620855B CN 202010536642 A CN202010536642 A CN 202010536642A CN 111620855 B CN111620855 B CN 111620855B
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benzoxanthene
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陈倩倩
黄冲
张世才
程大兴
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Yantai Jiumu Chemical Co ltd
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Abstract

本发明涉及一种含苯并氧杂蒽类化合物材料，所述化合物的结构式如化学式1所示：

Description

一种含苯并氧杂蒽类化合物材料及其应用
技术领域
本发明涉及一种含苯并氧杂蒽类化合物材料及其应用，属于半导体技术领域。
背景技术
有机电致发光(OLED:Organic Light Emission Diodes)器件技术是一种新型显示技术，该技术可以用来制造新型照明产品，也可以用来制造新型显示产品，应用前景十分广泛，并且很有希望取代现有的液晶显示和荧光照明。OLED发光器件由电极材料及夹在电极材料间的有机功能材料组成，其中，各种不同功能材料根据用途相互叠加在一起。当对其两端电极施加电压，并通过电场作用在有机功能材料层中的正负电荷时，正负电荷进一步在发光层中复合，即产生OLED电致发光。
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括空穴注入材料、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。因此开发新型结构的功能材料就显得至关重要。
发明内容
本发明针对现有技术存在的不足，提供一种含苯并氧杂蒽类化合物材料及其应用，所述的含苯并氧杂蒽类化合物材料热稳定性好，合成方法简单易操作，使用所述的含苯并氧杂蒽类化合物材料制备的有机电致发光器件具有良好的发光效率和寿命表现。
本发明解决上述技术问题的技术方案如下：一种含苯并氧杂蒽类化合物材料，所述化合物的结构式如化学式1所示：
Figure BDA0002537292040000011
其中，所述Ar独立的表示取代或非取代的C6～C60的芳基或者C6～C60的杂环基，其碳原子可置换为至少一个选自氮、氧或硫的杂原子。
优选的，所述Ar为选自下述结构中的任意一个：
Figure BDA0002537292040000021
Figure BDA0002537292040000031
优选的，所述含苯并氧杂蒽类化合物材料为如下结构式中的任意一个：
Figure BDA0002537292040000032
Figure BDA0002537292040000041
Figure BDA0002537292040000051
所述的含苯并氧杂蒽类化合物材料的制备方法，包括以下步骤：
①中间体C的合成：在氮气保护下，反应瓶中加入四氢呋喃和原料A，降温至-95℃以下滴加n-BuLi(正丁基锂正己烷溶液)，滴毕计时保温1h，后滴加原料B的四氢呋喃溶液，滴毕跟踪液相数据保温3h反应结束，经水解、萃取、水洗、柱层析、重结晶得到中间体C，总收率75％，液相检测纯度为99.5％。所述原料A与原料B的摩尔比为1:1，所述原料A与n-BuLi(正丁基锂正己烷溶液)的摩尔比为1:1.1。
中间体C核磁数据：1H NMR:δ7.25-7.42(9H,7.30,7.35,7.32,7.36,7.34),7.59,7.76,7.89-7.96(4H,7.92,7.89).
②化学式1所示最终产品的合成：在氮气气氛下，将原料D加入到二氯甲烷中，随后加入三氟化硼乙醚溶液，降温至-15～-20℃滴加中间体C的二氯乙烷溶液，滴毕计时保温，保温3h反应合格，后经水解、水洗、柱层析、重结晶得到化学式1产品。
化学式1产品核磁数据：1H NMR:δ7.14-7.42(13H,7.25,7.27,7.18,7.22,7.21,7.25,7.31,7.36),7.48-7.59(2H,7.50,7.55),7.54-7.69(5H,7.66,7.68,7.59,7.55),7.85(2H),7.91(2H).
化学式1产品总收率80％，液相检测纯度95％。所述原料D与中间体C的摩尔比为1:0.98，所述原料D与三氟化硼乙醚溶液的摩尔比为1:1.03。其合成路线如下：
Figure BDA0002537292040000052
其中：Ar与化学式1中限定的范围一致。
本发明还公开了一种含苯并氧杂蒽类化合物材料的应用，所述的含苯并氧杂蒽类化合物材料用于制备有机电致发光器件。
进一步的，所述的有机电致发光器件包括至少一层功能层含有所述的含苯并氧杂蒽类化合物材料。
进一步的，所述的有机电致发光器件包括电子阻挡层，所述电子阻挡层材料为所述的含苯并氧杂蒽类化合物材料。
进一步的，所述的有机电致发光器件包括发光层，所述发光层含有所述的含苯并氧杂蒽类化合物材料。
本发明的有益效果是：本发明提供的含苯并氧杂蒽类化合物有机化合物，其可应用于OLED发光器件制作，并且与已知OLED材料相比，无论是效率、还是寿命均获得较大改观，特别是器件的寿命衰减获得较大的提升；
本发明提供的含苯并氧杂蒽类化合物有机化合物的制备方法简单易行，产率高，适于工业化生产。
具体实施方式
为使本发明的上述目的、特征和优点能够更加明显易懂，下面对本发明的具体实施方式做详细的说明。在下面的描述中阐述了很多具体细节以便于充分理解本发明。但是本发明能够以很多不同于在此描述的其它方式来实施，本领域技术人员可以在不违背本发明内涵的情况下做类似改进，因此本发明不受下面公开的具体实施例的限制。
除非另有定义，本文所使用的所有的技术和科学术语与属于本发明的技术领域的技术人员通常理解的含义相同。本文中在本发明的说明书中所使用的术语只是为了描述具体的实施方式的目的，不是旨在于限制本发明。
实施例1：化合物1的合成
在氮气保护下，反应瓶中加入四氢呋喃500g和原料A50g，降温至-95～-100℃滴加140ml n-BuLi(正丁基锂正己烷溶液)，滴毕计时保温1h，原料B 94g加入到940g四氢呋喃中，溶解后滴入反应体系中，滴毕保温3h反应结束，后将反应液缓慢滴入水中水解，然后加入600g甲苯萃取，水洗三次接近中性后经柱层析分离、重结晶得到中间体C 89.2g，总收率75％，液相纯度99.5％。
Figure BDA0002537292040000071
在氮气气氛下，反应瓶中加入27g原料D-1与270g二氯甲烷，随后加入35.5g三氟化硼乙醚溶液，将中间体C 89g溶于890g二氯甲烷中，降温至-15～-20℃滴加中间体C的二氯甲烷溶液，滴毕计时保温，保温3h反应合格，后经水解、水洗、柱层析、重结晶得到88.9g中间体1，总收率80％，液相检测纯度为95％。
在氮气气氛下，反应瓶中依次加入t-BuONa(叔丁醇钠)23.2g，原料D-255.8g，中间体188.0g，甲苯880g，通N2 10min后加入Pd(OAc)2(醋酸钯)0.421g和三环己基膦1.1g，升温至100～105℃保温10h反应合格，后经水洗、柱层析、重结晶得到77.3g化合物1，总收率65％，反应液相纯度85％。
化合物1核磁数据：1H NMR:δ7.20-7.42(11H,7.31,7.25,7.22,7.21,7.26,7.33),7.46-7.70(8H,7.55,7.63,7.65,7.55,7.52,7.61,7.59),7.74,7.81-7.89(4H,7.87,7.86),7.90-7.96(4H,7.92,7.90),8.03-8.15(3H,8.07,8.08,8.13),8.19(1H),8.28-8.38(2H,8.31,8.35),8.47(1H).
实施例2：化合物2的合成
Figure BDA0002537292040000072
按照摩尔比1:1.1:2称取化合物D-3、中间体1和t-BuONa(叔丁醇钠)，加入催化剂Pd(OAc)2醋酸钯和S-phos(2-二环己基膦-2',6'-二甲氧基联苯)，溶剂为二甲苯，溶剂量为化合物D-3重量的8倍，在125℃下保温反应8h，液相检测，中间体1基本无剩余，反应液相纯度98.2％。经过降温过滤、水煮、打浆、重结晶得到化合物2，收率：85.5％，液相纯度为99.3％。
化合物2核磁数据：1H NMR:δ7.20-7.45(13H,7.34,7.27,7.42,7.22,7.21,7.28,7.39,7.31),7.53-7.63(3H,7.62,7.57),7.66-7.76(2H,7.72,7.73),7.77-7.95(10H,7.83,7.81,7.84,7.84,7.89,7.90,7.91,7.95),7.96(1H),8.23(1H),8.51(1H).
实施例3：化合物3的合成
Figure BDA0002537292040000081
按照摩尔比1:1.1:2称取化合物D-4、中间体1和t-BuONa(叔丁醇钠)，加入催化剂Pd(PPh3)2Cl2(双(三苯基膦)二氯化钯)和X-phos(2-二环己基膦-2’，4’,6’-三异丙基联苯)，溶剂为甲苯，溶剂量为化合物D-4重量的10倍，在95℃下保温反应12h，液相检测，反应纯度98.2％。经过降温过滤、水煮、打浆、重结晶得到化合物3，收率：75.5％，液相纯度为98.5％。
化合物3核磁数据：1H NMR:δ7.20-7.52(16H,7.32,7.27,7.38,7.42,7.45,7.24,7.21,7.25,7.36,7.31),7.60(2H),7.76-7.94(10H,7.87,7.89,7.85,7.77,7.97,7.90,7.85),7.95(1H).
实施例4：化合物4的合成
Figure BDA0002537292040000082
按照摩尔比1:1.5:2.5称取化合物D-5、中间体1和碳酸铯，加入催化剂Pd2(dba)3(三(二亚苄基丙酮)二钯)和X-phos(2-二环己基膦-2’,4’,6’-三异丙基联苯)，溶剂为四氢呋喃，溶剂量为化合物D-5重量的6倍，在75℃下保温反应3h，液相检测，反应纯度91.2％。经过降温过滤、水煮、打浆、重结晶得到化合物4，收率：86.3％，液相纯度为99.5％。
化合物4核磁数据：1H NMR:δ7.20-7.55(13H,7.46,7.49,7.36,7.31,7.25,7.22,7.24,7.28),7.60(2H),7.65-7.95(11H,7.91,7.92,7.88,7.93,7.88,7.84,7.74,7.66),8.03(1H),8.11(2H),8.16-8.25(4H,8.25,8.21,8.23,8.18),8.50-8.56(2H,8.55,8.56),8.72(1H).
实施例5：化合物5的合成
Figure BDA0002537292040000091
按照摩尔比1:1:2.2称取中间体1、化合物D-6和叔丁醇钾，加入催化剂Pd(OAc)2(醋酸钯)和三叔丁基膦四氟硼酸盐，溶剂为DMF(N,N-二甲基甲酰胺)，溶剂量为化合物D-6重量的10倍，在85℃下保温反应6h，液相检测，反应纯度90.5％。经过降温过滤、水煮、溶解分水、脱色过柱、打浆得到化合物5，收率：78.6％，液相纯度为99.1％。
化合物5核磁数据：1H NMR:δ1.87(6H),7.19-7.45(16H,7.42,7.38,7.33,7.28,7.23,7.26,7.25,7.25,7.28,7.33,7.29),7.56-7.69(4H,7.66,7.62,7.65),7.73-7.98(10H,7.77,7.78,7.83,7.85,7.90,7.93,7.86,7.91),7.99(1H).
实施例6：化合物6的合成
Figure BDA0002537292040000092
按照摩尔比1:1:3称取中间体1、化合物D-5和t-BuONa(叔丁醇钠)，加入催化剂Pd2(dba)3(三(二亚苄基丙酮)二钯)和4,5-双二苯基膦-9,9-二甲基氧杂蒽，溶剂为二甲苯，溶剂量为化合物D-7重量的10倍，在115℃下保温反应8h，液相检测，反应纯度90.5％。经过降温过滤、水煮、溶解分水、脱色过柱、打浆得到化合物6，收率：87.8％，液相纯度为99.5％。
化合物6核磁数据：1H NMR:δ7.20-7.53(16H,7.28,7.27,7.24,7.22,7.26,7.36,7.45,7.48,7.43,7.35,7.34),7.60(2H),7.81-8.03(12H,7.95,8.01,7.96,7.97,7.98,7.92,7.93,7.83,7.85,7.96),8.24(1H).
含有苯并氧杂蒽类化合物中，其结构式有(1)-(36)中的任意一个：
Figure BDA0002537292040000101
Figure BDA0002537292040000111
化合物(1)-(36)的质谱数据如下表1：
表1质谱数据
Figure BDA0002537292040000112
Figure BDA0002537292040000121
器件实施例1：一种有机电致发光器件，其制备步骤包括：
将透明玻璃基板层上的ITO阳极层用蒸馏水清洗3次，超声波清洗15min，蒸馏水清洗结束后，然后依次用去丙酮、异丙醇、乙醇超声清洗各15分钟后干燥，然后在等离子体清洗器中处理2分钟。在准备好的ITO阳极层上，通过真空蒸镀方式依次蒸镀空穴注入层材料2-TNATA/30nm；空穴传输材料NPB/50nm；蒸镀实施例1中的化合物1作为主体材料，掺杂5％Ir(ppy)3混合，厚度为30nm；的电子传输材料TPBI/40nm；电子注入层LiF/1nm；蒸镀阴极Al(100nm)。
器件实施例2：本实施例与器件实施例1的不同之处在于：电致发光器件的发光层主体材料为本发明化合物2。
器件实施例3：本实施例与器件实施例1的不同之处在于：电致发光器件的发光层主体材料为本发明化合物3。
器件实施例4：本实施例与器件实施例1的不同之处在于：电致发光器件的发光层主体材料为本发明化合物4。
器件实施例5：本实施例与器件实施例1的不同之处在于：电致发光器件的发光层主体材料为本发明化合物5。
器件实施例6：本实施例与器件实施例1的不同之处在于：电致发光器件的发光层主体材料为本发明化合物6。
对比实施例1：本实施例与器件实施例1的不同之处在于：电致发光器件的发光层主体材料为已知的CBP材料。
将器件实施例1-6和比较实施例1得到的有机电致发光器件进行性能检测，检测数据如下表2。
表2器件实施例的检测数据
Figure BDA0002537292040000131
以上结果表明，本发明的苯并氧杂蒽类化合物应用于有机发光器件中，尤其是作为主体材料，表现出高发光效率、驱动电压低的优点，是性能良好的有机发光材料。
以上所述实施例的各技术特征可以进行任意的组合，为使描述简洁，未对上述实施例中的各个技术特征所有可能的组合都进行描述，然而，只要这些技术特征的组合不存在矛盾，都应当认为是本说明书记载的范围。
以上所述实施例仅表达了本发明的几种实施方式，其描述较为具体和详细，但并不能因此而理解为对发明专利范围的限制。应当指出的是，对于本领域的普通技术人员来说，在不脱离本发明构思的前提下，还可以做出若干变形和改进，这些都属于本发明的保护范围。因此，本发明专利的保护范围应以所附权利要求为准。

Claims (6)

1.一种含苯并氧杂蒽类化合物材料，其特征在于，所述化合物的结构式如化学结构式1所示：
Figure FDA0003510359030000011
所述Ar为选自下述结构中的任意一个：
Figure FDA0003510359030000012
2.根据权利要求1所述的一种含苯并氧杂蒽类化合物材料，其特征在于，所述含苯并氧杂蒽类化合物材料为如下结构式中的任意一个：
Figure FDA0003510359030000013
Figure FDA0003510359030000021
3.一种根据权利要求1或2所述的一种含苯并氧杂蒽类化合物材料的应用，其特征在于，所述的含苯并氧杂蒽类化合物材料用于制备有机电致发光器件。
4.根据权利要求3所述的一种含苯并氧杂蒽类化合物材料的应用，其特征在于，所述的有机电致发光器件包括至少一层功能层含有所述的含苯并氧杂蒽类化合物材料。
5.根据权利要求3所述的一种含苯并氧杂蒽类化合物材料的应用，其特征在于，所述的有机电致发光器件包括电子阻挡层，所述电子阻挡层材料为所述的含苯并氧杂蒽类化合物材料。
6.根据权利要求3所述的一种含苯并氧杂蒽类化合物材料的应用，其特征在于，所述的有机电致发光器件包括发光层，所述发光层含有所述的含苯并氧杂蒽类化合物材料。
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