CN112645791A - 一种新型的oled材料及其制备方法与应用 - Google Patents
一种新型的oled材料及其制备方法与应用 Download PDFInfo
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Abstract
Description
技术领域
本发明涉及一种新型的OLED材料及其制备方法与应用,属于有机电致发光技术领域。
背景技术
有机电致发光二级管(OLED)因其自身的诸多优点,如其自身可发光、视角广、工作电压低、响应速度快、反应时间短、面板薄、可实现柔性显示等,被认为是下一代显示技术的主流。
用于有机电致发光器件的材料主要包括电极材料、载流子传输材料、发光材料,其中发光材料在OLED中占有重要位置。
为了实现全彩显示,分别需要红、绿、蓝三种颜色的发光器件,与红光器件和绿光器件相比,蓝色发光器件尚不够成熟,器件寿命和效率偏低。人们正通过超净技术,封装技术,开发具有高玻璃化转变温度的蓝光材料等来提高蓝光器件的寿命,而掺杂技术和开发具有两极结构的新型材料,则是提高器件效率的方向。
掺杂技术是通过将发光材料(客体材料)分散在其它材料(主体材料)之中,来降低发光材料的浓度,从而避免分子间聚集和浓度淬灭,进而实现提高器件效率,改善电致发光色纯度,延长器件寿命的目的。
就当前OLED显示照明产业的实际需求而言,目前OLED材料的发展还远远不够,落后于面板制造企业的要求,作为材料企业开发更高性能的有机功能材料显得尤为重要。
发明内容
本发明针对现有技术存在的不足,提供一种具有较高的热稳定性及发光效率的新型有机电致发光材料及其制备方法与应用。
本发明解决上述技术问题的技术方案如下:一种新型的OLED材料,所述的OLED材料具有符合式(I)所示的分子结构:
其中,Ar1和Ar2分别独立的选自C6-C60的芳基、含有N、S、O的C6-C60杂芳基、C7-C61的芳烷基,Ar1和Ar2相同或者不同。
进一步的,所述的Ar1和Ar2分别独立的选自如下结构式中的任意一种:
进一步的,所述的OLED材料选自如下结构式中的任意一种:
本发明还公开了新型的OLED材料的制备方法,所述的制备方法包括如下步骤:
A、将原料1-溴-2-苯乙烯基苯加入到有机溶剂中溶解后降温至-78℃,滴加正丁基锂,然后滴加2,6-二溴蒽醌溶液,反应完毕淬灭,处理得到粗品,粗品在酸溶液中回流,反应结束后提取反应产物,即得到中间体M-1,其反应方程式为:
B、将步骤A得到的中间体M-1、二苯甲酮、锌粉加入到有机溶剂降温至-78℃,滴加四氯化钛,滴加完毕升温至室温,然后回流反应,应完毕后提取反应产物,经硅胶柱层析和重结晶,即得到中间体M-2,其反应方程式为:
C、将步骤B得到的中间体M-2、芳胺ArH或芳基硼酸ArB(OH)2(当Ar1和Ar2不相同时为Ar1B(OH)2和Ar2B(OH)2)、催化剂和配体、碱性物质加入到有机溶剂中进行反应,反应完毕后提取反应产物,即得到最终产品,其反应方程式为:
所述的Ar、Ar1、Ar2分别独立的选自C6-C60的芳基、含有N、S、O的C6-C60杂芳基或C7-C61的芳烷基。
进一步的,所有步骤均在惰性气体的保护下进行,其中惰性气体选择氮气或氩气。
进一步的,在步骤A中,反应温度为-100~-50℃;在步骤B中,反应温度为-100~-50℃;在步骤C中,反应温度为60~200℃。
进一步的,在步骤A至步骤C中,所述有机溶剂为N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、甲苯、二甲苯、均三甲苯、邻二氯苯、二氯乙烷、二氯甲烷、四氢呋喃、二氧六环中的一种或任意几种的混合物。
进一步的,在步骤C中,所述催化剂为Pd(OAc)2、Pd(PPh3)4、Pd(PPh3)2Cl2或Pd2(dba)3中的一种或多种混合;所述的配体为邻菲啰啉、三苯基膦、三环己基膦、三环戊基膦、三叔丁基膦四氟硼酸、(9,9-二甲基-9H-氧杂蒽-4,5-二取代)双(二苯基膦)中的一种或多种的混合物;所述的碱性物质为叔丁醇钠、叔丁醇钾、无水磷酸钾、碳酸钠、碳酸钾或碳酸铯中的一种或多种混合。
进一步的,在步骤A中,所述2,6-二溴蒽醌与1-溴-2-苯乙烯基苯的摩尔比为1:(1.0-2.0),所述1-溴-2-苯乙烯基苯与正丁基锂的摩尔比例1:(1.0-1.5);
在步骤B中,所述中间体M-1与二苯甲酮的摩尔比为1:(1.0-1.5),所述中间体M-1与锌粉的摩尔比为1:(2.0-6.0),所述中间体M-1与四氯化钛的摩尔比为1:(2.0-6.0);
在步骤C中,所述M-2与ArH的摩尔比为1:(1.0-3.0),所述M-2与ArB(OH)2的摩尔比为1:(1.0-3.0),所述M-2与钯催化剂的摩尔比为1:(0.001-0.05),所述钯催化剂与配体的摩尔比为1:(1.0-4.0),所述M-2与碱性物质的摩尔比为1:(1.0-3.0)。
本发明还公开了所述新型的OLED材料的应用:
所述的OLED材料应用于有机电致发光器件,所述有机发光器件中至少一个功能层中含有所述的OLED材料。
进一步的,所述的OLED材料应用于所述有机电致发光器件的发光层。
本发明的有益效果是:
1)本发明提供的OLED材料,其制备方法简单,热稳定性好;
2)以本发明提供的OLED材料作为功能层,制作的有机电致发光器件,具有良好的光电性能;
3)以本发明材料作为掺杂材料,以BH-1为主体材料的OLED器件,在电流密度为20mA/cm2,器件的LT95寿命可达300~346(Hr)@5000nits,电流效率7.89~8.49cd/A。
附图说明
图1为实施例中所述有机电致发光器件的结构示意图;
图中,1透明基板层,2阳极层,3空穴注入层,4空穴传输层,5电子阻挡层,6发光层,7空穴阻挡/电子传输层,8电子注入层,9阴极。
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。
本发明有机电致发光器件结构示意图如图1所示,器件中所用到的一些有机化合物的分子结构式如下所示:
M-2的制备
步骤(1):在500mL三口瓶中,加入1-溴-2-苯乙烯基苯(5.18g,0.02mol),100g无水四氢呋喃,降温至-78℃,滴加0.022mol正丁基锂,滴毕于-78℃保温搅拌2h,将2,6-二溴蒽醌(8.05g,0.022mol)加50g四氢呋喃溶解,缓慢滴加至反应体系中,滴加结束,-78℃保温反应1h,随后升温至室温反应2h。反应结束后,加少量水淬灭反应,加二氯甲烷萃取,收集有机相,脱除溶剂后,得到粗品。
将上述粗品于氮气保护下,加到60g冰醋酸中,100~110℃保温反应4h。反应结束后脱除溶剂,过硅胶柱层析纯化,洗脱剂为二氯甲烷:石油醚=1:10,进一步使用甲苯/乙醇重结晶纯化,得到7.9g化合物M-1,收率74.8%。高分辨质谱,ESI源,分子式C28H16Br2O,理论值525.9568,测试值525.9552。
步骤(2):取M-1(5.28g,0.01mol)、二苯甲酮(2.19g,0.012mol)、锌粉(2.62g,0.04mol)、100g无水四氢呋喃加到500mL三口瓶中,氮气保护下降温至-78℃,滴加0.02mol四氯化钛,滴毕缓慢升温至室温,然后加热至60~65℃保温反应10h。反应结束后滴加饱和碳酸钠水溶液,析出白色固体,过滤,粗品过硅胶柱层析纯化,洗脱剂为二氯甲烷:石油醚=1:8,进一步使用甲苯/乙醇重结晶纯化,得到5.4g化合物M-2,收率79.6%。高分辨质谱,ESI源,分子式C41H26Br2,理论值676.0401,测试值676.0439。
合成实施例:
实施例1化合物C01的制备
在100mL三口瓶中,加入化合物M-2(3.39g,0.005mol)、苯硼酸(1.34g,0.011mol)、碳酸钾(2.76g,0.02mol)、四三苯基膦合钯(0.058g,5×10-5mol)、水15mL、甲苯80mL,氮气保护下,升温至内温80~90℃,保温反应12h,降至室温,将反应液转移至250mL分液漏斗中分掉下层水相,上层有机相继续用50mL水洗涤,脱除溶剂后,收集固体,过硅胶柱层析纯化,洗脱剂为二氯甲烷:石油醚=1:6,进一步使用甲苯重结晶纯化,得到2.22g目标物C01,收率66.0%。高分辨质谱,ESI源,分子式C53H36,理论值672.2817,测试值672.2850。
1H NMR(CDCl3):6.88(s,2H),7.16~7.55(m,32H),7.82(s,1H),7.98(s,1H).
实施例2化合物C02的制备
以化合物M-2和1-萘硼酸为原料,按照实施例1中所述方法制备化合物C02,收率70.2%。高分辨质谱,ESI源,分子式C61H40,理论值772.3130,测试值772.3156。
1H NMR(CDCl3):6.86(s,2H),7.18~7.61(m,28H),7.83(s,1H),7.97(s,1H),8.05~8.10(m,4H),8.38~8.43(dd,2H),8.52~8.58(dd,2H).
实施例3化合物C03的制备
以化合物M-2和4-联苯硼酸为原料,按照实施例1中所述方法制备化合物C03,收率67.4%。高分辨质谱,ESI源,分子式C65H44,理论值824.3443,测试值824.3469。
1H NMR(CDCl3):6.86(s,2H),7.18~7.64(m,40H),7.84(s,1H),8.05(s,1H).
实施例4化合物C04的制备
以化合物M-2和9-蒽硼酸为原料,按照实施例1中所述方法制备化合物C04,收率63.7%。高分辨质谱,ESI源,分子式C69H44,理论值872.3443,测试值872.3409。
1HNMR(CDCl3):6.88(s,2H),7.16~7.53(m,30H),7.81(s,1H),7.91~8.06(m,9H),8.22~8.28(dd,2H)
实施例5化合物C05的制备
以化合物M-2和9-菲硼酸为原料,按照实施例1中所述方法制备化合物C05,收率70.3%。高分辨质谱,ESI源,分子式C69H44,理论值872.3443,测试值872.3462。
1HNMR(CDCl3):6.87(s,2H),7.18~7.52(m,22H),7.82~7.94(m,12H),8.10~8.20(m,4H)8.90~8.95(dd,4H).
实施例6化合物C06的制备
以化合物M-2和荧蒽-3-硼酸为原料,按照实施例1中所述方法制备化合物C06,收率59.8%。高分辨质谱,ESI源,分子式C73H44,理论值920.3443,测试值920.3488。
1HNMR(CDCl3):6.88(s,2H),7.16~7.60(m,24H),7.78~7.98(m,10H),8.10~8.15(dd,4H)8.43~8.48(dd,4H).
实施例7化合物C07的制备
以化合物M-2和荧蒽-3-硼酸为原料,按照实施例1中所述方法制备化合物C07,收率57.4%。高分辨质谱,ESI源,分子式C73H44,理论值920.3443,测试值920.3406。
1HNMR(CDCl3):6.86(s,2H),7.17~7.62(m,22H),7.72~8.08(m,13H),
8.14~8.16(d,2H),8.20(S,1H),8.28~8.34(dd,2H),8.52~8.54(d,2H).
实施例8化合物C08的制备
以化合物M-2和三亚苯-2-硼酸为原料,按照实施例1中所述方法制备化合物C08,收率55.6%。高分辨质谱,ESI源,分子式C77H48,理论值972.3756,测试值972.3725。
1HNMR(CDCl3):6.86(s,2H),7.25~7.53(m,22H),7.82~8.14(m,18H),8.90~9.86(dd,4H),9.16(s,2H).
实施例9化合物C09的制备
以化合物M-2和二苯并呋喃-4-硼酸为原料,按照实施例1中所述方法制备化合物C09,收率62.4%。高分辨质谱,ESI源,分子式C65H40O2,理论值852.3028,测试值852.3077。
1HNMR(CDCl3):6.86(s,2H),7.20~7.48(m,26H),7.53~7.63(dd,2H),7.80~7.92(m,8H),8.15(s,2H).
实施例10化合物C10的制备
以化合物M-2和9,9-二甲基芴-2-硼酸为原料,按照实施例1中所述方法制备化合物C10,收率63.3%。高分辨质谱,ESI源,分子式C71H52,理论值904.4069,测试值904.4103。
1HNMR(CDCl3):1.69(s,12H),6.90(s,2H),7.10~7.62(m,28H),7.70~7.95(m,8H),8.05~8.15(d,2H).
实施例11化合物C11的制备
以化合物M-2和咔唑为原料,按照实施例1中所述方法制备化合物C11,收率60.7%。高分辨质谱,ESI源,分子式C65H42N2,理论值850.3348,测试值850.3379。
1HNMR(CDCl3):6.88(s,2H),7.11~7.50(m,32H),7.52~7.56(dd,2H),7.95~8.12(m,4H),8.52~8.57(dd,2H).
实施例12化合物C12的制备
以化合物M-2和三苯胺-4-硼酸为原料,按照实施例1中所述方法制备化合物C12,收率54.6%。高分辨质谱,ESI源,分子式C77H54N2,理论值1006.4287,测试值1006.4261。
1HNMR(CDCl3):6.89(s,2H),7.05~7.50(m,50H),7.76(s,1H),7.96(s,1H).
实施例13化合物C13的制备
在100mL三口瓶中,加入化合物M-2(6.78g,0.01mol)、苯硼酸(1.34g,0.011mol)、碳酸钾(2.76g,0.02mol)、四三苯基膦合钯(0.116g,10-4mol)、水15mL、甲苯80mL,氮气保护下,升温至内温80~90℃,保温反应12h,降至室温,将反应液转移至250mL分液漏斗中分掉下层水相,上层有机相继续用50mL水洗涤,脱除溶剂后,收集固体,过硅胶柱层析纯化,洗脱剂为乙酸乙酯:石油醚=1:5,进一步使用甲苯石油醚重结晶纯化,得到5.27g中间体,收率78.0%。
在100mL三口瓶中,加入上述中间体化合物(3.38g,0.005mol)、1-萘硼酸(1.03g,0.006mol)、碳酸钾(1.38g,0.01mol)、四三苯基膦合钯(0.058g,5×10-5mol)、水15mL、甲苯80mL,氮气保护下,升温至内温80~90℃,保温反应12h,降至室温,将反应液转移至250mL分液漏斗中分掉下层水相,上层有机相继续用50mL水洗涤,脱除溶剂后,收集固体,过硅胶柱层析纯化,洗脱剂为乙酸乙酯:石油醚=1:5,进一步使用甲苯石油醚重结晶纯化,得到2.31g中间体,收率63.9%。高分辨质谱,ESI源,分子式C57H38,理论值722.2947,测试值722.2988。
1HNMR(CDCl3):6.88(s,2H),7.08~7.81(m,31H),7.98(s,1H),8.04~8.10(m,2H),8.48~8.52(dd,1H),8.82~8.84(dd,1H).
实施例14化合物C14的制备
以化合物M-2和苯硼酸、9-菲硼酸为原料,按照实施例13中所述方法制备化合物C14,收率57.7%。高分辨质谱,ESI源,分子式C61H40,理论值772.3130,测试值772.3108。
1HNMR(CDCl3):6.89(s,2H),7.18~7.55(m,27H),7.82~7.96(m,7H),8.25~8.29(dd,2H),9.03~9.10(dd,2H).
实施例15化合物C15的制备
以化合物M-2和苯硼酸、荧蒽-3-硼酸为原料,按照实施例13中所述方法制备化合物C15,收率52.5%。高分辨质谱,ESI源,分子式C63H40,理论值796.3130,测试值796.3188。
1HNMR(CDCl3):6.88(s,2H),7.15~7.95(m,34H),8.08~8.12(m,2H),8.40~8.44(m,2H).
实施例16化合物C16的制备
以化合物M-2和1-萘硼酸、9-蒽硼酸为原料,按照实施例13中所述方法制备化合物C16,收率59.2%。高分辨质谱,ESI源,分子式C65H42,理论值822.3287,测试值822.3242。
1HNMR(CDCl3):6.90(s,2H),7.20~7.62(m,29H),7.83~8.08(m,8H),8.32(s,1H),8.50~8.55(dd,1H),8.83~8.87(dd,1H).
实施例17化合物C17的制备
以化合物M-2和1-萘硼酸、二苯并呋喃-4-硼酸为原料,按照实施例13中所述方法制备化合物C17,收率51.7%。高分辨质谱,ESI源,分子式C63H40O,理论值812.3079,测试值812.3042。
1HNMR(CDCl3):6.89(s,2H),7.15~7.62(m,29H),7.80~8.06(m,7H),8.48~8.53(dd,1H),8.84~8.88(dd,1H).
实施例18化合物C18的制备
以化合物M-2和1-萘硼酸、N-苯基咔唑-3-硼酸为原料,按照实施例13中所述方法制备化合物C18,收率58.2%。高分辨质谱,ESI源,分子式C69H45N,理论值887.3552,测试值887.3544。
1HNMR(CDCl3):6.90(s,2H),7.11~7.24(m,8H),7.34~7.64(m,24H),7.75~7.90(m,7H),8.17(s,1H),8.50~8.55(m,2H),8.95(s,1H).
实施例19化合物C19的制备
以化合物M-2和荧蒽-3-硼酸、4-(1-苯基-1H-苯并咪唑-2-基)苯硼酸为原料,按照实施例13中所述方法制备化合物C19,收率50.4%。高分辨质谱,ESI源,分子式C76H48N2,理论值988.3817,测试值988.3854。
1HNMR(CDCl3):6.91(s,2H),7.14~7.39(m,14H),7.44~7.62(m,19H),7.79~7.98(m,8H),8.08~8.13(t,2H),8.40~8.45(dd,2H),8.56~8.60(dd,1H).
有机电致发光器件实施例:
以下通过器件实施例1-19和器件比较例1详细说明本发明合成的OLED材料在器件中的应用效果。
器件比较例1
具体制备过程如下:
如图1所示,透明基板层1为透明PI膜,对ITO阳极层2(膜厚为150nm)进行洗涤,即依次进行碱洗涤、纯水洗涤、干燥,再进行紫外线-臭氧洗涤以清除阳极层2表面的有机残留物。在进行了上述洗涤之后的阳极层2上,利用真空蒸镀装置,蒸镀膜厚为10nm的HT-1和P-1作为空穴注入层3,HT-1和P-1的质量比为98:2。接着蒸镀55nm厚度的HT-1作为空穴传输层4。随后蒸镀10nm厚度的EB-1作为电子阻挡层5。上述电子阻挡材料蒸镀结束后,制作OLED发光器件的发光层6,其结构包括OLED发光层6所使用化合物BH-1作为主体材料,BD-1作为掺杂材料,掺杂材料掺杂比例为3%重量比,发光层6膜厚为20nm。在上述发光层6之后,继续真空蒸镀ET-1和Liq,ET-1和Liq质量比为1:1,膜厚为35nm,此层为空穴阻挡/电子传输层7。在空穴阻挡/电子传输层7上,通过真空蒸镀装置,制作膜厚为1nm的Yb层,此层为电子注入层8。在电子注入层8上,通过真空蒸镀装置,制作膜厚为80nm的Mg:Ag电极层,Mg、Ag质量比为1:9,此层为阴极层9。按照上述步骤完成电致发光器件的制作后,测量器件的效率数据和光衰寿命,相关材料的分子结构式如下所示:
本发明器件实施例1-19与器件比较例1相比器件的制作工艺完全相同,并且所采用了相同的基板材料和电极材料,电极材料的膜厚也保持一致,所不同的是对器件中的发光层材料做了更换。各器件实施例的层结构和测试结果分别如表1和表2所示:
表1各器件实施例的层结构
表2各器件实施例和器件比较例的效率和寿命数据
注:驱动电压和电流效率都是在10mA/cm2下测试的数据;驱动电压和电流效率均是通过弗士达IVL测试系统测试;LT95指的是电流效率都是在20mA/cm2下,器件亮度衰减到初始亮度的95%所用的时间;寿命测试系统为日本系统技研公司EAS-62C型OLED器件寿命测试仪。
由表2的器件数据结果可以看出,本发明的有机发光器件无论是在驱动电压、器件效率还是寿命均相对于已知的掺杂材料的OLED器件获得较大的提升。
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 (10)
4.一种根据权利要求1-3任意一项所述的一种新型的OLED材料的制备方法,其特征在于,所述的制备方法包括如下步骤:
A、将原料1-溴-2-苯乙烯基苯加入到有机溶剂中溶解后降温至-78℃,滴加正丁基锂,然后滴加2,6-二溴蒽醌溶液,反应完毕淬灭,处理得到粗品,粗品在酸溶液中回流,反应结束后提取反应产物,即得到中间体M-1,其反应方程式为:
B、将步骤A得到的中间体M-1、二苯甲酮、锌粉加入到有机溶剂降温至-78℃,滴加四氯化钛,滴加完毕升温至室温,然后回流反应,应完毕后提取反应产物,经硅胶柱层析和重结晶,即得到中间体M-2,其反应方程式为:
C、将步骤B得到的中间体M-2、芳胺ArH或芳基硼酸ArB(OH)2或Ar1B(OH)2和Ar1B(OH)2、催化剂和配体、碱性物质加入到有机溶剂中进行反应,反应完毕后提取反应产物,即得到最终产品,其反应方程式为:
所述的Ar、Ar1、Ar2分别独立的选自C6-C60的芳基、含有N、S、O的C6-C60杂芳基或C7-C61的芳烷基。
5.根据权利要求4所述的一种新型的OLED材料的制备方法,其特征在于,所有步骤均在惰性气体的保护下进行,所述惰性气体选择氮、氩气;
在步骤A中,反应温度为-100~-50℃;在步骤B中,反应温度为-100~-50℃;在步骤C中,反应温度为60~200℃。
6.根据权利要求4所述的一种新型的OLED材料的制备方法,其特征在于,在步骤A至步骤C中,所述有机溶剂为N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、甲苯、二甲苯、均三甲苯、邻二氯苯、二氯乙烷、二氯甲烷、四氢呋喃、二氧六环中的一种或任意几种的混合物。
7.根据权利要求4所述的一种新型的OLED材料的制备方法,其特征在于,在步骤C中,所述催化剂为Pd(OAc)2、Pd(PPh3)4、Pd(PPh3)2Cl2或Pd2(dba)3中的一种或多种混合;所述的配体为邻菲啰啉、三苯基膦、三环己基膦、三环戊基膦、三叔丁基膦四氟硼酸、(9,9-二甲基-9H-氧杂蒽-4,5-二取代)双(二苯基膦)中的一种或多种的混合物;所述的碱性物质为叔丁醇钠、叔丁醇钾、无水磷酸钾、碳酸钠、碳酸钾或碳酸铯中的一种或多种混合。
8.根据权利要求4所述的一种新型的OLED材料的制备方法,其特征在于,在步骤A中,所述2,6-二溴蒽醌与1-溴-2-苯乙烯基苯的摩尔比为1:(1.0-2.0),所述1-溴-2-苯乙烯基苯与正丁基锂的摩尔比例1:(1.0-1.5);
在步骤B中,所述中间体M-1与二苯甲酮的摩尔比为1:(1.0-1.5),所述中间体M-1与锌粉的摩尔比为1:(2.0-6.0),所述中间体M-1与四氯化钛的摩尔比为1:(2.0-6.0);
在步骤C中,所述M-2与ArH的摩尔比为1:(1.0-3.0),所述M-2与ArB(OH)2的摩尔比为1:(1.0-3.0),所述M-2与钯催化剂的摩尔比为1:(0.001-0.05),所述钯催化剂与配体的摩尔比为1:(1.0-4.0),所述M-2与碱性物质的摩尔比为1:(1.0-3.0)。
9.一种根据权利要求1-3任意一项所述的一种新型的OLED材料的应用,其特征在于,所述的OLED材料应用于有机电致发光器件,所述有机发光器件中至少一个功能层中含有所述的OLED材料。
10.根据权利要求9所述的一种新型的OLED材料的应用,其特征在于,所述的OLED材料应用于所述有机电致发光器件的发光层。
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