CN115260138A - 一种空穴类有机电致发光化合物及其制备方法和应用 - Google Patents
一种空穴类有机电致发光化合物及其制备方法和应用 Download PDFInfo
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- CN115260138A CN115260138A CN202210945973.7A CN202210945973A CN115260138A CN 115260138 A CN115260138 A CN 115260138A CN 202210945973 A CN202210945973 A CN 202210945973A CN 115260138 A CN115260138 A CN 115260138A
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- nitrogen
- organic electroluminescent
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- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
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- 238000001819 mass spectrum Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- GIFAOSNIDJTPNL-UHFFFAOYSA-N n-phenyl-n-(2-phenylphenyl)naphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1C1=CC=CC=C1 GIFAOSNIDJTPNL-UHFFFAOYSA-N 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
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- 229920000642 polymer Polymers 0.000 description 1
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- 238000003825 pressing Methods 0.000 description 1
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
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- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
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- 238000001308 synthesis method Methods 0.000 description 1
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- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
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- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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Abstract
本发明公开了一种空穴类有机电致发光化合物及其制备方法和应用,本发明所提供的空穴类有机发光材料,配合物上的胺单元不仅具有较低的离子化电位,较好的给电子性,较高的空穴迁移率,还能降低分子的对称性,增加分子的构象异构体。同时,并环的特殊结构,使化合物具有刚性结构,增加了分子量,使得分子间不易结晶、不易聚集,从而使材料具有较高的光热稳定性。得到的空穴传输材料在用于有机电致发光器件后,可降低光电器件的驱动电压,显著提高光电器件的发光效率以及延长光电器件的使用寿命。
Description
技术领域
本发明属于有机光电材料领域,具体是一种空穴类有机电致发光化合物及其制备方法和应用。
背景技术
有机电致发光二极管(以下简称OLED)作为一种重要的电致发光器件,以其主动发光不需要背光源、发光效率高、可视角度大、响应速度快、温度适应的范围大、能耗小、更轻更薄、柔性显示等优点以及巨大的应用前景,吸引着众多研究者的关注。
有机电致发光元件是利用了如下原理的自发光元件:通过施加电场,利用由阳极注入的空穴与由阴极注入的电子的复合能使荧光性物质发光。它具有如下结构:阳极、阴极以及介于两者之间的有机材料层。为了提高有机电致发光元件的效率和稳定性,有机材料层通常包括具有不同材料的多层,例如空穴注入层(HIL)、空穴传输层(HTL)、发光层、电子传输层(ETL)和电子注入层(EIL)。在这种有机发光元件中,当在阳极和阴极之间施加电压时,来自阳极的空穴和来自阴极的电子注入有机材料层,产生的激子在迁移至基态时产生具有特定波长的光。其中空穴传输层可改变空穴到发光层的空穴传输效率、发光效率、寿命等。因此,目前使用铜酞菁(CuPc)、4,4′-双[N-(1-萘基)-N-苯基氨基]联苯(NPB)、N,N′-二苯基-N,N′-双(3-甲基苯基)-(1,1′-联苯)-4,4′-二胺(TPD)等作为空穴传输材料。使用这些材料的有机电致发光元件虽然在空穴传输效率、发光效率、寿命等方面有所提高,但是在使用寿命方面仍然不是很理想。
因此,结合上述问题,提供开发新型结构的空穴传输材料以改善有机电致发光元件在使用寿命上的不足,是本领域技术人员亟需解决的问题。
发明内容
本发明为了解决现有的有机EL装置的寿命不理想的技术问题,提供一种空穴类有机电致发光化合物及其制备方法和有机电致发光器件,本发明提供的化合物制备的器件具有极佳发光效率与较长的使用寿命。
为了实现上述目的,本发明采用如下技术方案:
本发明提供一种空穴类有机电致发光化合物,其结构通式1如下:
式中:
X和Y各自独立地选自C-R4/R5、N-R6、O或S;
m和n各自独立地选自0或1的整数,且m和n不同时为0;
L1和L2各自独立地选自为连接键、经取代或未经取代的C6-C30亚芳基、经取代或未经取代的3元-20元亚杂芳基,其杂原子选自氧(O)、氮(N)、硫(S)。
环B为稠合在苯环上的取代基,环B可稠合在苯环的任意位置。
环B选自取代或未经取代的C3-C30环烷基、取代或未经取代的3元-30元杂环烷基,其杂原子选自氧(O)、氮(N)、硫(S);经取代或未经取代的C6-C30芳基、经取代或未经取代的3元-20元杂芳基,其杂原子选自氧(O)、氮(N)、硫(S);经取代或未经取代的3元-25元杂芳基胺基,其杂原子选自氧(O)、氮(N)、硫(S);经取代或未经取代的C6~C60芳基胺基。
R1、R2、R3彼此相同或不同,并且各自独立地选自氢、氘、卤素、氰基、羧基、硝基、羟基、氨基、磺酸基、磺酰基、磷酸基、磷酰基、硅基、硼烷基;取代或未经取代的C1-C30烷基、取代或未经取代的C2-C30烯基、取代或未经取代的C2-C30炔基、取代或未经取代的C3-C30环烷基、取代或未经取代的3元-30元杂环烷基,其杂原子选自氧(O)、氮(N)、硫(S);经取代或未经取代的C6-C30芳基、经取代或未经取代的3元-20元杂芳基,其杂原子选自氧(O)、氮(N)、硫(S);经取代或未经取代的3元-25元杂芳基胺基,其杂原子选自氧(O)、氮(N)、硫(S);经取代或未经取代的C6~C60芳基胺基、经取代或未经取代的(C1-C30)烷氧基、经取代或未经取代的C6-C60芳氧基。
R4~R6各自独立地选自经取代或未经取代的C1-C30烷基、经取代或未经取代C6-C30芳基、经取代或未经取代的3元-30元杂芳基,其杂原子选自氧(O)、氮(N)、硫(S);或与相邻取代基连接形成单环或多环C3-C30脂环族环或C3-C30芳香族环,其碳原子可置换为至少一个选自氮、氧和硫的杂原子。
Ar1-Ar4彼此相同或不同,并且各自独立地选自经取代或未经取代的C1-C30烷基、取代或未经取代的C3-C30环烷基、取代或未经取代的3元-20元杂环烷基,其杂原子选自氧(O)、氮(N)、硫(S);经取代或未经取代的(C6-C30)芳基或经取代或未经取代的3元-30元杂芳基,其杂原子选自氧(O)、氮(N)、硫(S);经取代或未经取代的3元-15元杂芳基胺基,其杂原子选自氧(O)、氮(N)、硫(S);经取代或未经取代的C6~C60芳基胺基。
进一步优选,L1、L2各自独立地选自为连接键、经取代或未经取代的C6-C20亚芳基、经取代或未经取代的3元-18元亚杂芳基,其杂原子选自氧(O)、氮(N)、硫(S)。
进一步优选,环B选自经取代或未经取代的C6-C30芳基、经取代或未经取代的3元-20元杂芳基,其杂原子选自氧(O)、氮(N)、硫(S);
进一步优选,R1、R2、R3彼此相同或不同,并且各自独立地为氢、氘、卤素、氰基;取代或未经取代的C1-C10烷基、取代或未经取代的C3-C10环烷基、取代或未经取代的3元-10元杂环烷基,其杂原子选自氧(O)、氮(N)、硫(S);经取代或未经取代的C6-C20芳基、经取代或未经取代的3元-10元杂芳基,其杂原子选自氧(O)、氮(N)、硫(S);经取代或未经取代的3元-15元杂芳基胺基,其杂原子选自氧(O)、氮(N)、硫(S);经取代或未经取代的C6~C20芳基胺基。
进一步优选,Ar1-Ar4彼此相同或不同,并且各自独立地表示取代或未经取代的C6-C20芳基、经取代或未经取代的3元-15元杂芳基,其杂原子选自氧(O)、氮(N)、硫(S);经取代或未经取代的3元-15元杂芳基胺基,其杂原子选自氧(O)、氮(N)、硫(S);经取代或未经取代的C6~C30芳基胺基。
上述术语中,“取代”意指与化合物的碳原子键合的氢原子变成另外的取代基,并且取代的位置没有限制,只要该位置为氢原子被取代的位置(即,取代基可以取代的位置)即可,并且当两个或更多个取代基取代时,两个或更多个取代基可以彼此相同或不同
即上述的“取代或未经取代”中的“取代”,可优选的取代基为氘、氰基、卤素、硝基、羟基、磷酸基、硼烷基、硅基、C1~C8烷基、C2~C15烯基、C2~C10炔基、C6~C20芳基、C3~C10杂芳基、C1~C10烷氧基、C6~C20芳基氨基中的一种或多种。
在上述技术方案中,所述空穴类有机电致发光化合物选自所示结构的化合物:
本发明的发光材料通过以下反应流程来制备。
合成路线:通式1的合成
当L1或L2为非连接键时:
步骤1、中间体1的制备
将原料1(1.1eq)和原料2(1.0eq)加入到三口反应瓶中,分别加入四(三苯基膦钯)(0.01eq)和碳酸钾(2.0eq),再加入甲苯:乙醇:水=2:1:1混合液,氮气保护,升温到90℃回流过夜。反应完毕后,反应液降温到40-50℃,分去水层,用无水硫酸钠干燥有机层,旋干有机层得到固体有机物,使用少量的二氯甲烷将固体有机物完全溶解,然后缓慢滴加到石油醚溶液中,搅拌均匀,有沉淀析出,抽滤得固体,依次用无水乙醇、石油醚淋洗,烘干,获得中间体1;
步骤2、中间体2的制备
将中间体1(1.0eq)加入到反应瓶中,再加入(1.1eq)的碳酸钾,加入溶剂DMSO,氮气保护下,升温到160℃反应24小时。将反应液降到室温,加入水搅拌,再加入乙酸乙酯萃取反应液,得到的萃取液再用水洗涤一次,无水硫酸镁干燥,旋干得到油状物,利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得中间体2;
步骤3、中间体3的制备
将中间体2(1.0eq)和原料3(1.1eq)加入到反应瓶中,再分别加入Pd(oAc)2(0.05eq)、碳酸铯(2.0eq)、配体X-PHOS(0.11eq),加入乙二醇二甲醚(DME):水=2:1的混合溶液,氮气保护,升温回流反应16小时。处理过程:反应完毕后,反应液降温到40-50℃,分去水层,用无水硫酸钠干燥有机层,旋干有机层得到黑色状物,用二氯甲烷:石油醚=1:1过柱子,收集产品点,从而获得中间体3;
步骤4、通式式1的制备
将中间体3(1.0eq)和原料4(1.1eq)加入到反应瓶中,再分别加入Pd(oAc)2(0.05eq)、碳酸铯(2.0eq)、配体X-PHOS(0.11eq),加入乙二醇二甲醚(DME):水=2:1的混合溶液,氮气保护,升温回流反应16小时。处理过程:反应完毕后,反应液降温到40-50℃,分去水层,用无水硫酸钠干燥有机层,旋干有机层得到黑色状物,利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得通式1;
当L1或L2为连接键时:
步骤1、中间体1的制备
将原料1(1.1eq)和原料2(1.0eq)加入到三口反应瓶中,分别加入四(三苯基膦钯)(0.01eq)和碳酸钾(2.0eq),再加入甲苯:乙醇:水=2:1:1混合液,氮气保护,升温到90℃回流过夜。反应完毕后,反应液降温到40-50℃,分去水层,用无水硫酸钠干燥有机层,旋干有机层得到固体有机物,使用少量的二氯甲烷将固体有机物完全溶解,然后缓慢滴加到石油醚溶液中,搅拌均匀,有沉淀析出,抽滤得固体,依次用无水乙醇、石油醚淋洗,烘干,获得中间体1;
步骤2、中间体2的制备
将中间体1(1.0eq)加入到反应瓶中,再加入(1.1eq)的碳酸钾,加入溶剂DMSO,氮气保护下,升温到160℃反应24小时。将反应液降到室温,加入水搅拌,再加入乙酸乙酯萃取反应液,得到的萃取液再用水洗涤一次,无水硫酸镁干燥,旋干得到油状物,利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得中间体2;
步骤3、中间体3的制备
氮气保护下,将中间体2(1.0eq)和原料3(1.1eq)溶于甲苯溶液中,加入三(二亚苄基丙酮)二钯(0.01eq),三叔丁基膦(0.05eq)及叔丁醇钠(2.0eq),搅拌均匀,升温至回流,反应5h;反应结束后,稍降温度,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用乙酸乙酯萃取水相;合并有机相后,使用无水硫酸镁进行干燥,并且使用旋转式蒸发器去除溶剂;使用少量的二氯甲烷将固体有机物完全溶解,然后缓慢滴加到石油醚溶液中,搅拌均匀,有沉淀析出,抽滤得固体,依次用无水乙醇、石油醚淋洗,烘干,从而获得中间体3;
步骤4、通式1的制备
氮气保护下,将中间体3(1.0eq)和原料4(1.1eq)溶于甲苯溶液中,加入三(二亚苄基丙酮)二钯(0.01eq),三叔丁基膦(0.05eq)及叔丁醇钠(2.0eq),搅拌均匀,升温至回流,反应5h;反应结束后,稍降温度,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用乙酸乙酯萃取水相;合并有机相后,使用无水硫酸镁进行干燥,并且使用旋转式蒸发器去除溶剂;利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得通式1;
原料A的合成:(当X为O、S)
将A(1eq)加入到三口瓶中,再依次加入Pd(pph3)2约(0.1eq),CuI(2eq),Et3N(2eq)和干燥的DMF 200ml,最后加入B(2eq)。在氮气的保护下,将反应物升温到80℃反应48小时。冷却到室温,除去不溶物,将反应液倒入约1000ml水中,有固体析出,过滤干燥,过硅胶柱分离出纯品C。(石油醚:乙酸乙酯=10:1)。
将C(1eq)溶于200ml二氯甲烷中,室温下逐量加入NBS(1.1eq),过程持继10分钟左右,反应16小时。过滤除去不溶物,旋干滤液得固体,加入石油醚200ml、甲醇50ml和水100ml搅拌24小时,抽滤得到固体D。
将D(1eq)加入到反应瓶中,分别加入PdCl2(dppf)(0.03eq)、醋酸钾(2eq)和1,4-二氧六环200ml,氮气保护下升温到90℃反应6小时。后处理过程:降到室温,过滤,除去不溶物,旋干滤液,得到黑色油状物。过硅胶柱分离产物(二氯甲烷:石油醚=1:4),得到目标产物原料A。
原料A的合成:(当X为N)
将A2(1eq)溶于200ml二氯甲烷中,室温下逐量加入NBS(1eq),过程持继10分钟左右,反应16小时。过滤除去不溶物,旋干滤液得固体,加入石油醚300ml、甲醇50ml和水100ml搅拌24小时,抽滤得到固体D2。
将B2(1eq)、原料C2(1.1eq)、催化剂(0.01eq)和碳酸钾(2eq)依次加入到反应瓶中,氮气保护,加入甲苯、乙醇、水的2:1:1混合物约400ml,升温到90℃反应18小时。后处理过程:降温分液,无水硫酸镁干燥,旋干甲苯层,得到黑色油状物,过硅胶柱,二氯甲烷:石油醚=1:2淋洗,收集目标产品D2。
将干燥后的D2(1eq)加入到100ml的DMF中并滴入几滴乙酸,再加分批逐量加入NBS(1.1eq)升温到100℃反应过夜。待反应完毕后降温,将反应液倒入500ml水中,有大量固体析出,抽滤干燥得E2。
将E2(1eq)加入到反应瓶中,分别加入PdCl2(dppf)(0.03eq)、醋酸钾(2eq)和1,4-二氧六环200ml,氮气保护下升温到90℃反应6小时。后处理过程:降到室温,过滤,除去不溶物,旋干滤液,得到黑色油状物。过硅胶柱分离产物(二氯甲烷:石油醚=1:4),得到目标产物原料A。
原料A的合成:(当X为C)
将A3(1eq)溶解在100ml的二氯甲烷中备用。然后在80ml的二氯甲烷中,加入TiCl4(6eq)并搅拌,氮气保护下降温到-50℃保持30分钟,注入二甲基锌(6eq),溶液由无色变为橙棕色,-50℃搅拌1小时。再滴加A3的二氯甲烷溶液-50℃反应2小时。升温到-10℃加入冷的饱和氯化铵溶液搅拌30分钟,静止分液,有机层用盐水洗,无水硫酸钠干燥,浓缩得到油状物。过柱纯化,二氯甲烷:石油醚=1:10洗脱,得到无色油状物B3。
将化合物C3(1eq)溶解在200ml无水乙醇中,分别加入DDQ(1.1eq)和钯碳催化剂3g,升温回流反应4小时。降温过滤除去催化剂,浓缩得到产物C3。
将化合物C3(1eq)溶解在100ml二氯甲烷中,分批加入NBS(1eq),室温下反应过24小时。过滤除去不溶物,浓缩加入甲醇析出固体,再用水和甲醇冲洗滤饼,干燥得得化合物D3。
将化合物D3(1eq)和原料E3(1.1eq)加入到反应瓶中,加入四三苯基膦钯(0.01eq)和碳酸钾(2eq),再加入甲苯、乙醇和水的2:1:1的混合液400ml,升温到90℃反应16小时。降温,分液,水洗一次甲苯层,无水硫酸钠干燥,浓缩得到油状物,过硅柱,二氯甲烷:石油醚=1:4淋洗,得到白色固体F3。
将化合物F3 0.077mol溶解在100ml DMF中,分批加入NBS 0.093mol,升温到100℃反应过24小时。将反应液倒入300ml冷水中,搅拌有大量的固体析出,过滤得到深色产品,过硅柱,二氯甲烷:石油醚=1:4淋洗,得到白色固体G2。
将G3(1eq)加入到反应瓶中,分别加入PdCl2(dppf)(0.03eq)、醋酸钾(2eq)和1,4-二氧六环200ml,氮气保护下升温到90℃反应6小时。后处理过程:降到室温,过滤,除去不溶物,旋干滤液,得到黑色油状物。过硅胶柱分离产物(二氯甲烷:石油醚=1:4),得到目标产物原料A。
其中R1~R3、Ar1~Ar4、L1~L2、X、Y、环B、m和n如上述通式1中所定义。
本发明实施例的另一目的在于提供一种有机电致发光器件,包括第一电极、第二电极以及至少一层设置在所述第一电极和所述第二电极之间的有机物层。
本公开内容的有机发光器件的有机材料层可以形成为单层结构,但也可以形成为其中层和有两个或更多个有机材料层的多层结构。例如,本公开内容的有机发光器件可以具有包括空穴注入层、空穴传输层、空穴注入和传输层、电子阻挡层、发光层、电子传输层、电子注入层、空穴阻挡层、电子注入和传输层等作为有机材料层的结构。然而,有机发光器件的结构不限于此,并且可以包括更少数量的有机材料层或更多数量的有机材料层。
作为阳极材料,通常优选具有大功函数的材料使得空穴顺利注入有机材料层。在本公开内容中能够使用的阳极材料的具体实例包括:金属,例如钒、铬、铜、锌和金,或其合金;金属氧化物,例如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO);金属和氧化物的组合,例如ZnO:Al或SnO2:Sb;导电聚合物,例如聚(3-甲基噻吩)、聚[3,4-(乙烯-1,2-二氧)噻吩](PEDOT)、聚吡咯和聚苯胺,但不限于此。
空穴注入材料是有利地在低电压下接收来自阳极的空穴的材料,并且空穴注入材料的最高占据分子轨道(HOMO)优选地在阳极材料的功函数与周围有机材料层的HOMO之间。空穴注入材料的具体实例包括金属卟啉、低聚噻吩、基于芳基胺的有机材料、基于六腈六氮杂苯并菲的有机材料、基于喹吖啶酮的有机材料、基于苝的有机材料、蒽醌、以及基于聚苯胺和基于聚噻吩的导电聚合物等,但不限于此,并且还可以包含能够进行p掺杂的另外的化合物。
空穴传输材料是能够接收来自阳极或空穴注入层的空穴并将空穴传输至发光层的材料,并且具有高空穴迁移率的材料是合适的。其具体实例包括基于芳基胺的有机材料、导电聚合物、同时具有共轭部分和非共轭部分的嵌段共聚物等,但不限于此。
发光层可以发射红色、绿色或蓝色的光,并且可以由磷光材料或荧光材料形成。发光材料是能够通过接收分别来自空穴传输层和电子传输层的空穴和电子并使空穴与电子结合而发出在可见光区域内的光的材料,并且优选为对荧光或磷光具有有利的量子效率的材料。其具体实例包括:8-羟基喹啉铝配(Alq3);基于咔唑的化合物;二聚苯乙烯基化合物;BAlq;10-羟基苯并喹啉-金属化合物;基于苯并咔唑、基于苯并噻唑和基于苯并咪唑的化合物;基于聚(对亚苯基亚乙烯基)(PPV)的聚合物;螺环化合物;聚芴;红荧烯等,但不限于此。
发光层的主体材料包括稠合芳族环衍生物、含杂环的化合物等。具体地,稠合芳族环衍生物包括蒽衍生物、芘衍生物、萘衍生物、并五苯衍生物、菲化合物、荧蒽化合物等,含杂环的化合物包括咔唑衍生物、二苯并呋喃衍生物、梯子型呋喃化合物、嘧啶衍生物等,然而,材料不限于此。
电子传输层可以起到促进电子传输的作用。电子传输材料是有利地接收来自阴极的电子并将电子传输至发光层的材料,具有高电子迁移率的材料是合适的。其具体实例包括:8-羟基喹啉的Al配合物;包含Alq3的配合物;有机自由基化合物;羟基黄酮-金属配合物;等等,但不限于此。电子传输层的厚度可以为1nm至50nm。厚度为1nm或更大的电子传输层具有防止电子传输特性下降的优点,并且厚度为50nm或更小具有防止由电子传输层太厚引起的用于增强电子迁移的驱动电压增加的优点。
电子注入层可以起到促进电子注入的作用。电子注入材料优选为这样的化合物:其具有传输电子的能力,具有来自阴极的注入电子效应,对发光层或发光材料具有优异的电子注入效应,防止发光层中产生的激子迁移至空穴注入层,并且除此之外,具有优异的薄膜形成能力。其具体实例包括芴酮、蒽醌二甲烷、联苯醌、噻喃二氧化物、唑、二唑、三唑、咪唑、苝四羧酸、亚芴基甲烷、蒽酮等及其衍生物,金属配合物,含氮5元环衍生物等,但不限于此。
作为阴极材料,通常优选具有小功函数的材料使得电子顺利注入有机材料层。阴极材料的具体实例包括:金属,例如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅,或其合金;多层结构材料,例如LiF/Al或LiO2/Al等等,但不限于此。
本发明提供的有机电致发光器件可应用在有机发光器件(OLED)、有机太阳电池(OSC)、电子纸(e-paper)、有机感光体(OPC)或有机薄膜晶体管(OTFT)上。
经由上述的技术方案可知,与现有技术相比,本发明具有如下有益效果:
本发明提供了一种空穴传输材料,配合物上的胺单元不仅具有较低的离子化电位,较好的给电子性,较高的空穴迁移率,还能降低分子的对称性,增加分子的构象异构体。同时,并环的特殊结构,使化合物具有刚性结构,增加了分子量,使得分子间不易结晶、不易聚集,从而使材料具有较高的光热稳定性。得到的空穴传输材料在用于有机电致发光器件后,可降低光电器件的驱动电压,显著提高光电器件的发光效率以及延长光电器件的使用寿命。
具体实施方式
下面对本发明实施例中的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
实施例1:制备化合物H-1
将原料1(55mmol)和原料2(50mmol)加入到三口反应瓶中,分别加入四(三苯基膦钯)(0.50mmol)和碳酸钾(100mmol),再加入120.00ml甲苯:乙醇:水=2:1:1混合液,氮气保护,升温到90℃回流过夜。反应完毕后,反应液降温到40-50℃,分去水层,用无水硫酸钠干燥有机层,旋干有机层得到固体有机物,使用少量的二氯甲烷将固体有机物完全溶解,然后缓慢滴加到石油醚溶液中,搅拌均匀,有沉淀析出,抽滤得固体,依次用无水乙醇、石油醚淋洗,烘干,获得中间体1(13.9g,产率:76.5%,MW:364.71);
将中间体1(30mmol)加入到反应瓶中,再加入(33mmol)的碳酸钾,加入80.00ml的DMSO溶剂,氮气保护下,升温到160℃反应24小时。将反应液降到室温,加入水搅拌,再加入乙酸乙酯萃取反应液,得到的萃取液再用水洗涤一次,无水硫酸镁干燥,旋干得到油状物,利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得中间体2(6.8g,产率:66.3%,MW:344.92);
氮气保护下,将中间体2(15mmol)和原料3(16.5mmol)溶于90.00ml甲苯溶液中,加入三(二亚苄基丙酮)二钯(0.15mmol),三叔丁基膦(0.75mmol)及叔丁醇钠(30mmol),搅拌均匀,升温至回流,反应5h;反应结束后,稍降温度,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用乙酸乙酯萃取水相;合并有机相后,使用无水硫酸镁进行干燥,并且使用旋转式蒸发器去除溶剂;利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得化合物H-1(4.1g,产率:56.8%,Mw:477.73);
测试数据:
HPLC纯度:>99.5%。
元素分析:
计算值为:C,90.53;H,6.54;N,2.93。
测试值为:C,90.67;H,6.60;N,2.89。
实施例2:制备化合物H-28
将原料1(55mmol)和原料2(50mmol)加入到三口反应瓶中,分别加入四(三苯基膦钯)(0.50mmol)和碳酸钾(100mmol),再加入120.00ml甲苯:乙醇:水=2:1:1混合液,氮气保护,升温到90℃回流过夜。反应完毕后,反应液降温到40-50℃,分去水层,用无水硫酸钠干燥有机层,旋干有机层得到固体有机物,使用少量的二氯甲烷将固体有机物完全溶解,然后缓慢滴加到石油醚溶液中,搅拌均匀,有沉淀析出,抽滤得固体,依次用无水乙醇、石油醚淋洗,烘干,获得中间体1(13.6g,产率:74.8%,MW:364.80);
将中间体1(30mmol)加入到反应瓶中,再加入(33mmol)的碳酸钾,加入80.00ml的DMSO溶剂,氮气保护下,升温到160℃反应24小时。将反应液降到室温,加入水搅拌,再加入乙酸乙酯萃取反应液,得到的萃取液再用水洗涤一次,无水硫酸镁干燥,旋干得到油状物,利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得中间体2(6.7g,产率:65.2%,MW:344.81);
氮气保护下,将中间体2(15mmol)和原料3(16.5mmol)溶于90.00ml甲苯溶液中,加入三(二亚苄基丙酮)二钯(0.15mmol),三叔丁基膦(0.75mmol)及叔丁醇钠(30mmol),搅拌均匀,升温至回流,反应5h;反应结束后,稍降温度,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用乙酸乙酯萃取水相;合并有机相后,使用无水硫酸镁进行干燥,并且使用旋转式蒸发器去除溶剂;利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得化合物H-1(4.6g,产率:52.1%,Mw:593.88);
测试数据:
HPLC纯度:>99.5%。
元素分析:
计算值为:C,91.02;H,6.62;N,2.36。
测试值为:C,91.11;H,6.70;N,2.49。
实施例3:制备化合物H-34
将原料1(55mmol)和原料2(50mmol)加入到三口反应瓶中,分别加入四(三苯基膦钯)(0.5mmol)和碳酸钾(100mmol),再加入120.00ml甲苯:乙醇:水=2:1:1混合液,氮气保护,升温到90℃回流过夜。反应完毕后,反应液降温到40-50℃,分去水层,用无水硫酸钠干燥有机层,旋干有机层得到固体有机物,使用少量的二氯甲烷将固体有机物完全溶解,然后缓慢滴加到石油醚溶液中,搅拌均匀,有沉淀析出,抽滤得固体,依次用无水乙醇、石油醚淋洗,烘干,获得中间体1(13.9g,产率:75.7%,MW:364.83);
将中间体1(30mmol)加入到反应瓶中,再加入(33mmol)的碳酸钾,加入80.00ml的DMSO溶剂,氮气保护下,升温到160℃反应24小时。将反应液降到室温,加入水搅拌,再加入乙酸乙酯萃取反应液,得到的萃取液再用水洗涤一次,无水硫酸镁干燥,旋干得到油状物,利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得中间体2(6.9g,产率:66.8%,MW:344.84);
将中间体2(15mmol)和原料3(16.5mmol)加入到反应瓶中,再分别加入Pd(oAc)2(0.75mmol)、碳酸铯(30mmol)、配体X-PHOS(1.20mmol),加入100.00ml乙二醇二甲醚(DME):水=2:1的混合溶液,氮气保护,升温回流反应16小时。反应完毕后,反应液降温到40-50℃,分去水层,用无水硫酸钠干燥有机层,旋干有机层得到黑色状物,利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得化合物H-34(4.8g,产率:45.6%,Mw:705.98);
数据测试:
HPLC纯度:>99.5%。
元素分析:
计算值为:C,91.88;H,6.14;N,1.98。
测试值为:C,91.91;H,6.23;N,1.99。
原料A的合成:
将A1100mmol溶解在100ml的二氯甲烷中备用。然后在80ml的二氯甲烷中,加入TiCl4 600mmol并搅拌,氮气保护下降温到-50℃保持30分钟,注入二甲基锌600mmol,溶液由无色变为橙棕色,-50℃搅拌1小时。再滴加A1的二氯甲烷溶液-50℃反应2小时。升温到-10℃加入冷的饱和氯化铵溶液搅拌30分钟,静止分液,有机层用盐水洗,无水硫酸钠干燥,浓缩得到油状物。过柱纯化,二氯甲烷:石油醚=1:10洗脱,得到无色油状物B1(95.5%,18.97g,MW:198.69)。
将化合物B1 95mmol溶解在200ml无水乙醇中,分别加入DDQ 105mmol和钯碳催化剂3g,升温回流反应4小时。降温过滤除去催化剂,浓缩得到产物C1(97.2%,18.16g,MW:196.71)。
将化合物C1 90mmol溶解在100ml二氯甲烷中,分批加入NBS 90mmol,室温下反应过24小时。过滤除去不溶物,浓缩加入甲醇析出固体,再用水和甲醇冲洗滤饼,干燥得得化合物D1(96.5%,23.93g,MW:175.83)。
将化合物D1 80mmol和原料E1 80mmol加入到反应瓶中,加入四三苯基膦钯(0.8mmol)和碳酸钾(160mmol),再加入甲苯、乙醇和水的2:1:1的混合液400ml,升温到90℃反应16小时。降温,分液,水洗一次甲苯层,无水硫酸钠干燥,浓缩得到油状物,过硅柱,二氯甲烷:石油醚=1:4淋洗,得到白色固体F1(95.80%,15.07g,MW:196.60)。
将化合物F1 77mmol溶解在100ml DMF中,分批加入NBS 0.093mol,升温到100℃反应过24小时。将反应液倒入300ml冷水中,搅拌有大量的固体析出,过滤得到深色产品,过硅柱,二氯甲烷:石油醚=1:4淋洗,得到白色固体G1(94.9%,20.14g,MW:275.63)。
将G1 60mmol加入到反应瓶中,分别加入PdCl2(dppf)1.8mmol、醋酸钾120mmol和1,4-二氧六环200ml,氮气保护下升温到90℃反应6小时。后处理过程:降到室温,过滤,除去不溶物,旋干滤液,得到黑色油状物。过硅胶柱分离产物(二氯甲烷:石油醚=1:4),得到目标产物原料A(92.5%,17.91g,MW:322.69)。
其他化合物的合成方法与上述实施例相同,在此不一一赘述,其他合成实施例4-20的质谱和分子式如下表1所示:
表1:
采用上述实施例提供的空穴传输材料制备得到的有机电致发光器件,其中,该有机电致发光器件包括阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层、阴极。
当有机物层包括空穴传输层时,所述空穴传输层包括上述实施例提供的空穴传输材料。
具体地,有机电致发光器件的制备步骤如下:
器件实施例1:蓝光有机电致发光器件制备
所制备OLED器件的结构为:ITO阳极/HIL/HTL/EML/ETL/EIL/阴极
a、ITO阳极:将涂层厚度为的ITO(氧化铟锡)-Ag-ITO(氧化铟锡)玻璃基板在蒸馏水中清洗2次,超声波洗涤30min,再用蒸馏水反复清洗2次,超声波洗涤10min,洗涤结束后,用甲醇、丙酮、异丙醇依次超声波洗涤(每次洗涤5min),干燥,然后转移至等离子体清洗机内洗涤5min,再送至蒸镀机中,以该基板为阳极,在其上依次蒸镀其它功能层。
b、HIL(空穴注入层):以的蒸镀速率,真空蒸镀上述实施例提供的化合物H-1和P-dopant作为空穴注入层材料,其化学式如下所示。所述化合物H-1和P-dopant的蒸镀速率比为97:3,厚度为10nm;
e、EML(发光层):然后在上述电子阻挡层上,以的蒸镀速率,真空蒸镀厚度为20nm的主体材料(Host)和掺杂材料(Dopant)作为发光层。其Host和Dopant的化学式如下所示。其中Host和Dopant的蒸镀速率比为98:2。
K、随后将蒸镀完成的基板进行封装。首先采用涂胶设备将清洗后盖板用UV胶进行涂覆工艺,然后将涂覆完成的盖板移至压合工段,将蒸镀完成的基板置于盖板上端,最后将基板和盖板在贴合设备作用下进行贴合,同时完成对UV胶光照固化。
参照上述器件实施例1提供的方法,分别选用化合物H-2,H-5,H-8,H-11,H-15,H-23,H-28,H-30,H-34,H-38,H-42,H-50,H-55,H-58,H-65,H-68,H-72,H-75,H-80替代化合物H-1,进行空穴传输层的蒸镀,并制备得到相应的有机电致发光器件,分别记为器件实施例2-20。
器件对比例1:
该对比例提供了一种有机电致发光器件,该有机电致发光器件的制备方法与器件实施例1的唯一区别在于,该有机电致发光器件是采用现有的对比化合物1替代上述器件实施例1中的空穴传输材料(化合物H-1)进行蒸镀,制备得到相应的有机电致发光器件,记为器件对比例1。其中,对比化合物1的化学结构式为:
在1000(nits)亮度下对上述器件实施例1-20以及器件对比例1得到的有机电致发光器件的驱动电压、发光效率以及寿命进行表征,测试结果如下表2:
表2:
在蓝光顶发射器件中,电流效率受色度影响较大,因此将色度对效率的影响因素考虑进去,将电流效率与CIEy比值定义为BI值,即BI=(cd/A)/CIEy,
并由表2数据可知:由本发明提供的有机电致发光化合物作为空穴传输层制备的有机电致发光器件相对于对比化合物作为空穴传输层制备的有机电致发光器件,BI值、寿命等方面性能均有提升。
本说明书中各个实施例采用递进的方式描述,每个实施例重点说明的都是与其他实施例的不同之处,各个实施例之间相同相似部分互相参见即可。对于实施例公开的装置而言,由于其与实施例公开的方法相对应,所以描述的比较简单,相关之处参见方法部分说明即可。
对所公开的实施例的上述说明,使本领域专业技术人员能够实现或使用本发明。对这些实施例的多种修改对本领域的专业技术人员来说将是显而易见的,本文中所定义的一般原理可以在不脱离本发明的精神或范围的情况下,在其它实施例中实现。因此,本发明将不会被限制于本文所示的这些实施例,而是要符合与本文所公开的原理和新颖特点相一致的最宽的范围。
Claims (10)
1.一种空穴类有机电致发光化合物,其特征在于,其结构如通式1所示:
其中,式中:
X和Y各自独立地选自C-R4/R5、N-R6、O或S;
m和n各自独立地选自0或1的整数,且m和n不同时为0;
L1和L2各自独立地选自为连接键、经取代或未经取代的C6-C30亚芳基、经取代或未经取代的3元-20元亚杂芳基,其杂原子选自氧、氮、硫;
环B为稠合在苯环上的取代基且环B可稠合在苯环的任意位置;
环B选自经取代或未经取代的C3-C30环烷基、经取代或未经取代的3元-30元杂环烷基,其杂原子选自氧、氮、硫,经取代或未经取代的C6-C30芳基、经取代或未经取代的3元-20元杂芳基,其杂原子选自氧、氮、硫,经取代或未经取代的3元-25元杂芳基胺基,其杂原子选自氧、氮、硫,经取代或未经取代的C6~C60芳基胺基;
R1、R2、R3彼此相同或不同,并且各自独立地选自氢、氘、卤素、氰基、羧基、硝基、羟基、氨基、磺酸基、磺酰基、磷酸基、磷酰基、硅基、硼烷基、取代或未经取代的C1-C30烷基、取代或未经取代的C2-C30烯基、取代或未经取代的C2-C30炔基、取代或未经取代的C3-C30环烷基、取代或未经取代的3元-30元杂环烷基,其杂原子选自氧、氮、硫,经取代或未经取代的C6-C30芳基、经取代或未经取代的3元-20元杂芳基,其杂原子选自氧、氮、硫,经取代或未经取代的3元-25元杂芳基胺基,其杂原子选自氧、氮、硫,经取代或未经取代的C6~C60芳基胺基、经取代或未经取代的C1-C30烷氧基、经取代或未经取代的C6-C60芳氧基;
R4~R6各自独立地选自经取代或未经取代的C1-C30烷基、经取代或未经取代C6-C30芳基、经取代或未经取代的3元-30元杂芳基;
或,
与相邻取代基连接形成单环或多环C3-C30脂环族环或C3-C30芳香族环,其碳原子可置换为至少一个选自氮、氧或硫的杂原子;
Ar1-Ar4彼此相同或不同,并且各自独立地表示经取代或未经取代的C1-C30烷基、取代或未经取代的C3-C30环烷基、取代或未经取代的3元-20元杂环烷基、经取代或未经取代的C6-C30芳基或经取代或未经取代的3元-30元杂芳基、经取代或未经取代的3元-15元杂芳基胺基、经取代或未经取代的C6~C60芳基胺基。
2.根据权利要求1所述的一种空穴类有机电致发光化合物,其特征在于,L1和L2各自独立地选自为连接键、经取代或未经取代的C6-C20亚芳基或经取代或未经取代的3元-18元亚杂芳基。
3.根据权利要求1所述的一种空穴类有机电致发光化合物,其特征在于,环B选自经取代或未经取代的C6-C30芳基或经取代或未经取代的3元-20元杂芳基。
4.根据权利要求1所述的一种空穴类有机电致发光化合物,其特征在于,R1、R2和R3彼此相同或不同,并且各自独立地选自氢、氘、卤素、氰基、取代或未经取代的C1-C10烷基、取代或未经取代的C3-C10环烷基、取代或未经取代的3元-10元杂环烷基、经取代或未经取代的C6-C20芳基、经取代或未经取代的3元-10元杂芳基、经取代或未经取代的3元-15元杂芳基胺基、经取代或未经取代的C6~C20芳基胺基。
5.根据权利要求1所述的一种空穴类有机电致发光化合物,其特征在于,Ar1-Ar4彼此相同或不同,且各自独立地选自取代或未经取代的C6-C20芳基、经取代或未经取代的3元-15元杂芳基、经取代或未经取代的3元-15元杂芳基胺基、经取代或未经取代的C6~C30芳基胺基。
7.一种如权利要求1-6任一所述的空穴类有机电致发光化合物的制备方法,其特征在于,所述L1或L2为非连接链时,其合成路线如下:
具体制备步骤如下:
步骤1、中间体1的制备
将原料1和原料2加入到反应容器中,然后分别加入四(三苯基膦钯)和碳酸钾,再加入甲苯、乙醇和水的混合液,氮气保护,升温到90℃回流过夜,得到中间体1;
步骤2、中间体2的制备
将中间体1加入到反应瓶中,再加入碳酸钾,加入溶剂DMSO,氮气保护下,升温到160℃反应24h,得中间体2;
步骤3、中间体3的制备
将中间体2和原料3加入到反应容器中,再分别加入Pd(oAc)2、碳酸铯、配体X-PHOS,加入乙二醇二甲醚和水的混合溶液,氮气保护,升温回流反应16h,得中间体3;
步骤4、通式1的制备
将中间体3和原料4加入到反应容器中,再分别加入Pd(oAc)2、碳酸铯、配体X-PHOS,加入乙二醇二甲醚和水的混合溶液,氮气保护,升温回流反应16h,得通式1;
当所述L1或L2为连接链时,其合成路线如下:
具体制备步骤如下:
步骤A、中间体1的制备
将原料1和原料2加入到反应容器中,然后分别加入四(三苯基膦钯)和碳酸钾,再加入甲苯、乙醇和水的混合液,氮气保护,升温到90℃回流过夜,得中间体1;
步骤B、中间体2的制备
将中间体1加入到反应容器中,再加入碳酸钾,加入溶剂DMSO,氮气保护下,升温到160℃反应24h,得中间体2;
步骤C、中间体3的制备
氮气保护下,将中间体2和原料3溶于甲苯溶液中,然后加入三(二亚苄基丙酮)二钯,三叔丁基膦及叔丁醇钠,搅拌均匀,升温至回流,反应5h,得中间体3;
步骤D、通式1的制备
氮气保护下,将中间体3和原料4溶于甲苯溶液中,加入三(二亚苄基丙酮)二钯,三叔丁基膦及叔丁醇钠,搅拌均匀,升温至回流,反应5h,得通式1。
8.根据权利要求7所述的一种空穴类有机电致发光化合物的制备方法,其特征在于,
步骤1中所述原料1、和原料2、四(三苯基膦钯)和碳酸钾的摩尔比为1.1:1:0.01:2;所述甲苯、乙醇和水的体积比为2:1:1;
步骤2中所述中间体1和碳酸钾的摩尔比为1:1.1;
步骤3中所述中间体2、原料3、Pd(oAc)2、碳酸铯和配体X-PHOS的摩尔比为1:1.1:0.05:2:0.11;所述乙二醇二甲醚和水的体积比为2:1;
步骤4中所述中间体3、原料4、Pd(oAc)2、碳酸铯和配体X-PHOS的摩尔比为1:1.1:0.05:2:0.11;所述乙二醇二甲醚和水的体积比为2:1;
步骤A中所述原料1、原料2、四(三苯基膦钯)和碳酸钾的摩尔比为1.1:1:0.01:2;所述甲苯、乙醇和水的体积比为2:1:1;
步骤B中所述中间体1和碳酸钾的摩尔比为1:1.1;
步骤C中所述中间体2、原料3、三(二亚苄基丙酮)二钯、三叔丁基膦和叔丁醇钠的摩尔比为1:1.1:0.01:0.05:2;
步骤D中所述中间体3、原料4、三(二亚苄基丙酮)二钯、三叔丁基膦和叔丁醇钠的摩尔比为1:1.1:0.01:0.05:2。
9.一种有机电致发光器件,其特征在于,所述有机电致发光器件包括第一电极、第二电极以及至少一层设置在所述第一电极和所述第二电极之间的有机物层;其中,所述有机物层包括权利要求1-6任一所述的空穴类有机电致发光化合物。
10.如权利要求9所述的有机电致发光器件在有机发光器件、有机太阳电池、电子纸、有机感光体或有机薄膜晶体管中的应用。
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