CN111171045A - 一种稠合多环化合物及其制备方法和用途 - Google Patents
一种稠合多环化合物及其制备方法和用途 Download PDFInfo
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- CN111171045A CN111171045A CN202010102570.7A CN202010102570A CN111171045A CN 111171045 A CN111171045 A CN 111171045A CN 202010102570 A CN202010102570 A CN 202010102570A CN 111171045 A CN111171045 A CN 111171045A
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- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K85/60—Organic compounds having low molecular weight
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Abstract
本发明涉及显示技术领域,具体涉及一种稠合多环化合物及其制备方法和用途。本发明提供的稠合多环化合物,具有如通式Ⅳ所示的结构,该化合物结构具有双偶极性,主体材料的HOMO能级和LUMO能级可分别定位于不同的供电子基团和吸电子基团上,使得主体材料中电荷和空穴传输的平衡性好,扩大了发光层中空穴和电子复合的区域,降低激子浓度,防止器件的三线态‑三线态湮灭,提高了器件效率。
Description
技术领域
本发明涉及显示技术领域,具体涉及一种稠合多环化合物及其制备方法和用途。
背景技术
有机电致发光二极管(organic light-emitting diodes,OLEDs)由于响应快、能耗低、自发光、色域广、超薄、具有可折叠及柔性等优点,是未来比液晶显示技术更具有应用前景的新型显示技术,从而越来越受到人们的重视。
1987年,美国柯达公司(Eastman Kodak)实验室的邓青云等人首度利用真空蒸镀的方式制作成第一个有机发光二极管(organic light-emitting diodes,OLED)器件(以下简称OLED器件),其以透明且可以导电的氧化铟锡(ITO)作为阴极,并在上面依序蒸镀二胺基衍生物与三(8-羟基喹啉)铝,阳极材料则使用镁银合金,此种多层结构能降低OLED器件的驱动电压,并有效改善材料分子与电极界面间的电荷注入问题,器件效能与寿命也因而提升。
与传统技术相比,OLED器件拥有驱动电压低、发光效率高、对比度高、色饱和度高、视角广、及响应时间快等诸多优点。现今的OLED器件包含空穴注入层、空穴传输层、发光层、空穴阻挡层、电子传输层、及电子注入层中之复数层,并搭配合适之电极,该复数层分别由以下材料所构成:空穴注入材料、空穴传输材料、发光材料、空穴阻挡材料、电子传输材料、及电子注入材料,其中,采用掺杂方式制作的OLED发光层在器件的发光效率上具有优势,因此发光层材料常利用主体材料掺杂客体材料形成,而主体材料是影响OLED器件的发光效率和性能的重要因素。其中,4,4'-Bis(9H-carbazol-9-yl)biphenyl(CBP)是一种广泛应用的主体材料,具有良好的空穴传输性质,但CBP作为主体材料使用时,由于其玻璃态转变温度低,易于结晶,导致OLED器件的使用性能和发光效率降低。另一方面,材料分子量的增加,可以提高材料的玻璃态转变温度和热稳定性,但同时也会降低材料的三线态能级,影响器件的使用寿命和发光效率。
发明内容
本发明的目的在于克服现有技术中的发光层主体材料存在玻璃转化温度低、易结晶,热稳定性差,无法兼具良好的热稳定性与高三线态能级的缺陷。
为达到上述目的,本发明采用如下技术方案:
一种稠合多环化合物,具有如下所示的结构:
T1独立选自单键、NR15、S、O、BR15、PR15、C(R15)2,其中,R15相同或不同,并分别独立选自甲基、氘代甲基、苯基、氘代苯基、联苯基、氘代联苯基、萘基、氘代萘基;
T2和T3至少一个为单键,当T2为单键时,T3为S或O;当T3为单键时,T2为S或O;
R1-R14相同或不同,并分别独立选自氢、氘、甲基、氘代甲基、苯基、氘代苯基、氘代甲基取代苯基。
进一步的,R1-R14相同或不同,并至少一个选自氘、氘代甲基、氘代苯基、氘代甲基取代苯基中的一种。
进一步的,R1-R4相同或不同,并至少含有一个氢;和/或,
R5-R8相同或不同,并至少含有一个氢;和/或,
R9-R14相同或不同,并至少含有一个氢,优选R11-R14相同或不同,并至少含有一个氢。
进一步的,当T2为单键时,T3为S或O;
优选的,当T2为单键时,T3为S。
进一步的,具有如下所示的结构:
进一步的,所述稠合多环化合物具有下述任一所示的分子结构:
本发明还提供一种上述所述稠合多环化合物的制备方法,
当T1选自C(R15)2,即稠合多环化合物具有通式Ⅳ-1所示结构时,T4选自Cl C(R15)2或Br C(R15)2,其制备方法如下所示:
以式(E)所示的化合物为原料,在催化剂存在下经关环反应得到中间体化合物(F);中间体化合物(F)与式(G)所示的化合物在催化剂作用下经偶联反应得到通式Ⅳ-1所示化合物;
所述通式Ⅳ-1所示化合物的制备路径如下所示:
或当T1选自BR15,即稠合多环化合物具有通式Ⅳ-2所示结构时,T4选自氢,其制备方法如下所示:
以式(E)所示的化合物为原料,与式(H)所示的化合物在催化剂存在下反应得到中间体化合物(J);中间体化合物(J)与式(G)所示的化合物在催化剂作用下经偶联反应得到通式Ⅳ-2所示化合物;
所述通式Ⅳ-2所示化合物的制备路径如下所示:
或当T1选自O,即稠合多环化合物具有通式Ⅳ-3所示结构时,T4选自羟基,其制备方法如下所示:
以式(E)所示的化合物为原料,在催化剂存在下反应得到中间体化合物(K);中间体化合物(K)与式(G)所示的化合物在催化剂作用下经偶联反应得到通式Ⅳ-3所示化合物;
所述通式Ⅳ-3所示化合物的制备路径如下所示:
或当T1选自S,即稠合多环化合物具有通式Ⅳ-4所示结构时,T4选自巯基,其制备方法如下所示:
以式(E)所示的化合物为原料,在催化剂存在下反应得到中间体化合物(K-1);中间体化合物(K-1)与式(G)所示的化合物在催化剂作用下经偶联反应得到通式Ⅳ-4所示化合物;
所述通式Ⅳ-4所示化合物的制备路径如下所示:
或当T1选自PR15,即稠合多环化合物具有通式Ⅳ-5所示结构时,T4选自氢,其制备方法如下所示:
以式(E)所示的化合物为原料,在催化剂存在下反应得到中间体化合物(L);中间体化合物(L)在催化剂的作用下反应得到中间体化合物(M),中间体化合物(M)与式(N)所示的化合物在催化剂作用下经偶联反应得到中间体化合物(O),中间体化合物(O)与式(G)所示的化合物在催化剂作用下经偶联反应得到通式Ⅳ-5所示化合物;
所述通式Ⅳ-5所示化合物的制备路径如下所示:
或当T1选自NR15,即稠合多环化合物具有通式Ⅳ-6所示结构时,T4选自硝基,其制备方法如下所示:
以式(D)所示的化合物为原料,在催化剂存在下反应得到中间体化合物(P);中间体化合物(P)与式(Q)所示的化合物、式(G)所示的化合物相继反应得到通式Ⅳ-6所示化合物;
所述通式Ⅳ-6所示化合物的制备路径如下所示:
或当T1选自单键,即稠合多环化合物具有通式Ⅳ-7所示结构时,其制备方法如下所示:
以式(R)所示的化合物为原料,与式(S)所示的化合物在催化剂的作用下反应得到中间体化合物(T),中间体化合物(T)在催化剂的作用下关环反应得到中间体化合物(U),中间体化合物(U)与式(G)所示的化合物在催化剂作用下经偶联反应得到通式Ⅳ-7所示化合物;
所述通式Ⅳ-7所示化合物的制备路径如下所示:
其中,W选自氟、氯、溴或碘。
进一步的,所述式(E)所示的化合物的制备方法如下所示:
以式(A)所示的化合物为起始原料,在催化剂存在下经硝化反应得到中间体化合物(B);中间体化合物(B)与式(C)所示的化合物在催化剂作用下经偶联反应得到中间体化合物(D);中间体化合物(D)在催化剂作用下经还原反应得到式(E)所示的化合物;
所述式(E)所示化合物的制备路径如下所示:
本发明还提供一种电子器件,所述电子器件中包含上述所述的稠合多环化合物中的任意一种或至少两种组合;
优选的,所述电子器件为有机电致发光器件、有机场效应晶体管、有机薄膜晶体管、有机发光晶体管、有机集成电路、有机太阳能电池、有机场淬灭器件、发光电化学电池、有机激光二极管或有机光感受器中的任意一种。可选的,所述有机电致发光器件可为有机发光二极管。
进一步的,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阳极和阴极,以及位于阳极和阴极之间的有机薄膜层,所述有机薄膜层包括上述所述的稠合多环化合物中的任意一种或至少两种组合;
优选的,所述有机薄膜层包括发光层,还包括空穴注入层、空穴传输层、空穴阻挡层、电子传输层、电子注入层、电子阻挡层和电荷传输层中的任意一种或至少两种组合,所述发光层中包含上述所述的稠合多环化合物中的任意一种或至少两种组合;
优选的,所述发光层包括主体材料和客体材料;所述发光层中的主体材料包含上述所述的稠合多环化合物中的任意一种或至少两种组合。
本发明还提供一种显示装置,所述显示装置包括上述所述的电子器件。
本发明还提供一种照明装置,所述照明装置包括上述所述的电子器件。
本发明的有益效果:
1)本发明提供的稠合多环化合物,具有如通式Ⅳ所示的结构,该化合物结构具有双偶极性,主体材料的HOMO能级和LUMO能级可分别定位于不同的供电子基团和吸电子基团上,使得主体材料中电荷和空穴传输的平衡性好,扩大了发光层中空穴和电子复合的区域,降低激子浓度,防止器件的三线态-三线态湮灭,提高了器件效率。
同时,通式Ⅳ所示的结构,通过在苯环1、2位置处或2、3位置处或3、4位置处与连接形成共有一边的稠环,一方面使得化合物的结构共轭性更大,激发态的稳定性更好,刚性更强,材料的稳定性更好,有利于器件寿命的延长;同时上述化合物特定的结构更利于OLED器件主体材料载流子复合的区域远离发光层与空穴或者电子传输层的相邻界面,提高了OLED器件的色纯度,同时能够防止激子向传输层的回传,进一步提高器件效率。
本发明所述的稠合多环化合物的HOMO能级和LUMO能级与相邻的空穴传输层,电子传输层相匹配,使OLED器件具有较小的驱动电压。同时所述化合物在OLED器件中作为发光层的主体材料,具有高的三线态能级和良好的热稳定性,能够保障能量由主体材料向客体材料的有效传递,并防止发光层材料分子结晶。
本发明所述化合物具有小的单线态(ΔES1)和三线态能级差(ΔET1),促进三线态激子向单线态激子的反系间窜越;另一方面,主体材料三线态T1向单线态S1转化的高反系间穿越(RISC)速率可以抑制从主体材料到发光染料的德克斯特能量转移(DET),促进能量转移,减少德克斯特能量转移(DET)的激子损失,避免有机电致发光器件的效率滚降效应,器件的外量子效率提高,从而实现高的器件效率。
2)本发明提供的稠合多环化合物,进一步的,R1-R14相同或不同,并至少一个选自氘、氘代甲基、氘代苯基、氘代甲基取代苯基中的一种,利用氘原子更低的势阱、更低的振动频率、更小的振幅以及更稳定的碳氘键,有利于提高有机电致发光器件的发光效率以及使用寿命。本发明通过限定R1-R4相同或不同,并至少含有一个氢;和/或,R5-R8相同或不同,并至少含有一个氢;和/或,R11-R14相同或不同,并至少含有一个氢,使得结构上的取代基不全为氘取代,该结构与结构相互作用,更利于提高器件的使用寿命。
3)本发明提供的有机电致发光(OLED)器件,所述发光层中的主体材料包含上述所述的稠合多环化合物中的任意一种或至少两种组合,上述特定的稠合多环化合物作为发光层的主体材料,使得主体材料中电荷和空穴传输的平衡性好,扩大了发光层中空穴和电子复合的区域,降低激子浓度,防止器件的三线态-三线态湮灭,提高了器件效率。
同时,上述化合物特定的结构更利于OLED器件主体材料载流子复合的区域远离发光层与空穴或者电子传输层的相邻界面,提高了OLED器件的色纯度,同时能够防止激子向传输层的回传,进一步提高器件效率。
本发明所述的稠合多环化合物的HOMO能级和LUMO能级与相邻的空穴传输层,电子传输层相匹配,使OLED器件具有较小的驱动电压。同时所述化合物在OLED器件中作为发光层的主体材料,具有高的三线态能级和玻璃态转变温度,以及良好的热稳定性,能够保障能量由主体材料向客体材料的有效传递,并防止发光层材料分子结晶。
本发明所述化合物的单线态能级高,能够保障主体材料向客体材料有效的能量传递,具有小的单线态(ΔES1)和三线态能级差(ΔET1),促进三线态激子向单线态激子的反系间窜越;另一方面,主体材料三线态T1向单线态S1转化的高反系间穿越(RISC)速率可以抑制从主体材料到发光染料的德克斯特能量转移(DET),促进能量转移,减少德克斯特能量转移(DET)的激子损失,避免有机电致发光器件的效率滚降效应,器件的外量子效率提高,从而实现高的器件效率。
附图说明
为了更清楚地说明本发明具体实施方式或现有技术中的技术方案,下面将对具体实施方式或现有技术描述中所需要使用的附图作简单地介绍,显而易见地,下面描述中的附图是本发明的一些实施方式,对于本领域普通技术人员来讲,在不付出创造性劳动的前提下,还可以根据这些附图获得其他的附图。
图1为本发明器件实施例1-11和对比例1-2中有机电致发光器件的结构示意图。
附图标记说明:
1-阳极,2-空穴注入层,3-空穴传输层,4-有机发光层,5-电子传输层,6-电子注入层,7-阴极。
具体实施方式
提供下述实施例是为了更好地进一步理解本发明,并不局限于所述最佳实施方式,不对本发明的内容和保护范围构成限制,任何人在本发明的启示下或是将本发明与其他现有技术的特征进行组合而得出的任何与本发明相同或相近似的产品,均落在本发明的保护范围之内。
实施例中未注明具体实验步骤或条件者,按照本领域内的文献所描述的常规实验步骤的操作或条件即可进行。所用试剂或仪器未注明生产厂商者,均为可以通过市购获得的常规试剂产品。
实施例1
本实施例提供一种稠合多环化合物,化合物10的合成路径如下所示:
化合物10的制备方法具体包括以下步骤:
1)中间体1-10的合成:在三口瓶中加入醋酸(500mL),加入化合物N3(72.0g,0.20mol),0℃下滴加质量分数65%浓硝酸(20.3g,0.21mol),滴加完毕,在0℃下搅拌2小时,反应液倒入800mL冰水中,加氢氧化钠中和至pH=6-7,用乙酸乙酯萃取(500mL×2),有机相合并后用饱和食盐水洗(200ml×2),硫酸钠干燥,有机相旋干得到粗产品78.2g,柱层析纯化(PE:EA=20:1-5:1)后,得中间体1-10(63.5g,产率为78.4%)。
2)中间体2-10的合成:在三口瓶中加入中间体1-10(40.5g,0.10mol),化合物N4(29.3g,0.10mol),碳酸钾(27.6g,0.20mol),四氢呋喃-水(四氢呋喃和水的体积比3:1,400mL),抽氮气保护,再加入四(三苯基膦)钯(1.0g),抽氮气保护,升温至75℃搅拌4小时,降温,加水(200mL)溶解后,乙酸乙酯萃取(200mL×2),有机相旋干后得到粗产品,柱层析纯化(PE:EA=10:1-5:1)后,得到中间体2-10(38.9g,产率74%)。
3)中间体3-10的合成:在醋酸(200mL)中加入中间体2-10(26.3g,0.050mol)加入铁粉(14g,0.25mol),室温搅拌2小时,过滤铁粉,醋酸旋干,得到粗产品,柱层析纯化(PE:EA=5:1-3:1)后,得到中间体3-10(19.7g,产率91.2%)。
4)中间体4-10的合成:三口瓶中加入中间体3-10(13.0g,0.030mol),二甲苯(120mL),质量分数10%的三叔丁基膦的二甲苯溶液(6.0g,4mol%,在三叔丁基膦的二甲苯溶液中三叔丁基膦为溶质,二甲苯为溶剂),叔丁醇钠(5.77g,0.060mol),抽氮气保护,再加入Pd2(dba)3(300mg,2.0mol%),再次抽氮气保护,升温至140℃,搅拌4小时,冷却到室温,二甲苯旋干后,直接柱层析纯化(PE:EA=5:1-2:1)后,得到中间体4-10(9.7g,产率77.8%)。
5)化合物10的合成:在三口瓶中加入中间体4-10(8.3g,0.020mol),化合物N1(7.2g,0.030mol),叔丁醇钠(3.85g,0.040mol),xphos(400mg),二甲苯(xylene,60mL),抽氮气保护,再加入四(三苯基膦)钯(200mg),再抽氮气保护,升温至140℃搅拌4小时,降温,有机相旋干后,柱层析纯化(PE:EA=4:1-2:1),得粗产物,粗产物用二甲苯、四氢呋喃各打浆三次后(100mL×6),得到化合物10(6.9g,产率56%)。
元素分析:(C43H28DN3S)理论值:C,83.20;H,4.87;N,6.77;S,5.16;实测值:C,83.23;H,4.86;N,6.76;S,5.15;HRMS(ESI)m/z(M+):理论值:620.2145;实测值:620.2151。
实施例2
本实施例提供一种稠合多环化合物,化合物11的合成路径如下所示:
化合物11的制备方法具体包括以下步骤:
1)中间体1-11的合成:其合成方法同中间体1-10的合成,区别在于用化合物N5(72克,0.2mol)替代化合物N3,得中间体1-11(63.2g,产率78%)。
2)中间体2-11的合成:其合成方法同中间体2-10的合成,区别在于用中间体1-11(40.49克,0.1mol)替代中间体1-10,用化合物N2(30.9克,0.1mol)替代化合物N4,得中间体2-11(40.2g,产率74.1%)。
3)中间体3-11的合成:其合成方法同中间体3-10的合成,区别在于用中间体2-11(27.1g,0.05mol)替代中间体2-10,得中间体3-11(20.6g,产率91.8%)。
4)中间体4-11的合成:其合成方法同中间体4-10的合成,区别在于用中间体3-11(13.4g,0.03mol)替代中间体3-10,得中间体4-11(9.8g,产率75.5%)。
5)化合物11的合成:其合成方法同化合物10的合成,区别在于用中间体4-11(8.64克,0.02mol)替代中间体4-10,得化合物11(8.1g,产率64%)。
元素分析:(C44H28D3N3S)理论值:C,82.99;H,5.38;N,6.60;S,5.03;实测值:C,82.97;H,5.38;N,6.61;S,5.03;HRMS(ESI)m/z(M+):理论值:636.2427;实测值:636.2433。
实施例3
本实施例提供一种稠合多环化合物,化合物14的合成路径如下所示:
化合物14的制备方法具体包括以下步骤:
化合物N6的合成路径如下所示:
2)中间体1-14的合成:取500毫升双颈圆底瓶,放入搅拌子并上接回流管,双颈圆底瓶干燥后充入氮气;向双颈圆底瓶中分别加入化合物N6(30.2g,1.2当量,0.12mol)、化合物N7(27.8g,1.0当量,0.1mol),碳酸钾(27.6g,2当量,0.2mol),四氢呋喃-水(四氢呋喃和水的体积比3:1,200mL),抽氮气保护,再加入四(三苯基膦)钯(6mmol),再抽氮气保护,升温至75℃搅拌4小时,降温,加水(150mL)溶解后,加乙酸乙酯(150mL×2)萃取,有机相旋干后得到粗产品,柱层析纯化(PE:EA=20:1-8:1)后,得到中间体1-14为黄色固体(32.9g,产率81%)。
3)中间体2-14的合成:取500毫升双颈圆底瓶,放入搅拌子并上接回流管,双颈圆底瓶干燥后充入氮气;向双颈圆底瓶中分别加入中间体1-14(40.6g,1当量,0.1mol),亚磷酸三乙酯(250mL),120℃搅拌16小时,冷却,溶剂旋干,加水(200mL),乙酸乙酯(200mL×2)萃取,合并有机相,有机相用饱和食盐水洗,硫酸钠干燥,旋干得到粗产品41.5g,柱层析纯化(PE:EA=10:1-5:1)后,旋干得到中间体2-14(30.5g,产率81.5%)。
4)化合物14的合成:取500毫升双颈圆底瓶,放入搅拌子并上接回流管,双颈圆底瓶干燥后充入氮气;向双颈圆底瓶中分别加入化合物N1(24g,1当量,0.1mol),中间体2-14(37.3g,1当量),tert-BuNa(叔丁醇钠,3当量),二甲苯(120毫升),xphos(1克),Pd[PPh3]4(四(三苯基膦)钯,0.05当量,5mmol),反应体系在140℃搅拌5小时,反应后冷却至室温,反应体系过滤,滤液浓缩,得粗产物;粗产物以层析纯化(乙酸乙酯/己烷,体积比1/10),得化合物14(42.2g,产率73%)。
元素分析:C40H22DN3S理论值:C,83.02;H,4.18;N,7.26;实测值:C,83.05;H,4.16;N,7.25;HRMS(ESI)m/z(M+):理论值:578.1675;实测值:578.1681。
实施例4
本实施例提供一种稠合多环化合物,化合物26的合成路径如下所示:
化合物26的制备方法具体包括以下步骤:
化合物N9的合成路径如下所示:
2)中间体1-26的合成:在三口瓶中加入化合物N9(81.0g,0.20mol),2-巯基-1-萘硼酸(化合物N10,49.2g,0.24mol),碳酸钾(55.2g,0.40mol),四氢呋喃-水(四氢呋喃和水的体积比3:1,600mL),抽氮气保护,再加入四(三苯基膦)钯(0.01mol),再抽氮气保护,升温至75℃搅拌4小时,降温,加水(300mL)溶解后,加乙酸乙酯(300mL×2)萃取,有机相旋干后得到粗产品,柱层析纯化(PE:EA=8:1-3:1)后,得到中间体1-26(61.3g,产率70%)。
3)中间体2-26的合成:在醋酸(300mL)中加入中间体1-26(43.8g,0.10mol)加入铁粉(28g,0.50mol),室温搅拌2小时,过滤铁粉,醋酸旋干,得到粗产品62克,柱层析纯化(PE:EA=5:1-2:1)后,得到中间体2-26(36.8g,产率90.2%)。
4)中间体3-26的合成:在三口瓶中将中间体2-26(20.4g,0.050mol)溶解于DMF(100mL),加入溴化钾(1.19g,0.010mol),在110℃反应12小时,冷却,溶剂旋干,加水(100mL)稀释,加乙酸乙酯(100mL×2)萃取,有机相合并后,加饱和食盐水洗(100mL×2),硫酸钠干燥,溶剂旋干后,得到粗产品3-26,柱层析纯化(PE:EA=3:1-1:1)后,旋干得到中间体3-26(13.0g,产率64%)。
5)化合物26的合成:在三口瓶中加入中间体3-26(8.1g,0.020mol),化合物N1(7.2g,0.030mol),叔丁醇钠(3.85g,0.040mol),xphos(400mg),二甲苯(60mL),抽氮气保护,再加入四(三苯基膦)钯(1mmol),再抽氮气保护,升温至140℃搅拌4小时,降温,有机相旋干后,柱层析纯化(PE:EA=4:1-2:1)后,得到化合物26粗产物,粗产物用二甲苯、四氢呋喃各打浆三次后(80mL×6),得到化合物26(7.8g,产率64%)。
元素分析:C40H22DN3S2理论值:C,78.66;H,3.96;N,6.88;实测值:C,78.64;H,3.96;N,6.89;HRMS(ESI)m/z(M+):理论值:610.1396;实测值:610.1400。
实施例5
本实施例提供一种稠合多环化合物,化合物74的合成路径如下所示:
化合物74的制备方法具体包括以下步骤:
化合物N11的合成路径如下所示:
2)中间体1-74的合成:在三口瓶中加入化合物N11(39.0g,0.10mol),化合物N12(21.7g,0.10mol),碳酸钾(27.6g,0.20mol),四氢呋喃-水(四氢呋喃和水的体积比3:1,400mL),抽氮气保护,再加入四(三苯基膦)钯(1.0g),再抽氮气保护,升温至75℃搅拌4小时,降温,加水(200mL)溶解后,乙酸乙酯萃取(200mL×2),有机相旋干后得到粗产品,柱层析纯化(PE:EA=20:1-10:1)后,得到中间体1-74(32.2g,产率74%)。
3)中间体2-74的合成:在三口瓶中加入中间体1-74(21.7g,0.05mol),加入异丙醇(200mL)溶解,加入二氧化钛(8.0g,0.10mol),氮气保护下,紫外灯光照反应16小时,溶剂旋干,残留物柱层析纯化(PE:EA=15:1-5:1)后,得到中间体2-74(12.6g,产率68%)。
4)化合物74的合成:在三口瓶中加入中间体2-74(7.4g,0.02mol),加入无水四氢呋喃(50mL),降温到-78℃,滴加苯基锂(20mL,0.02mol),保持温度-78℃搅拌2小时,再滴加化合物N1(4.8g,0.02mol)的四氢呋喃溶液(30mL),滴加完毕后,-78℃保温2小时,然后升到室温过夜,加水(100mL)淬灭,加乙酸乙酯(100mL×2)萃取,饱和食盐水洗,硫酸钠干燥,旋干得到粗产品,粗产物柱层析纯化(PE:EA=7:1-3:1)后,得到化合物74(8.2g,产率63%)。
元素分析:C46H27DN4O理论值:C,84.51;H,4.47;N,8.57;实测值:C,84.54;H,4.48;N,8.58;HRMS(ESI)m/z(M+):理论值:653.2326;实测值:653.2331。
实施例6
本实施例提供一种稠合多环化合物,化合物76的合成路径如下所示:
化合物76的制备方法具体包括以下步骤:
化合物N13的合成路径如下所示:
2)中间体1-76的合成:其合成方法同中间体1-74的合成,区别在于用化合物N14(21.8克,1当量,0.1mol)替代化合物N12,得中间体1-76(32.1克,产率71%)。
3)中间体2-76的合成:其合成方法同中间体2-74的合成,区别在于用中间体1-76(22.6克,0.05mol)替代中间体1-74,得中间体2-76(11.6克,产率60%)。
4)化合物76的合成:其合成方法同化合物74的合成,区别在于用中间体2-76(7.76克,0.02mol)替代中间体2-74,得化合物76(7.9克,产率59%)。
元素分析:C46H26D2N4S理论值:C,82.36;H,4.51;N,8.35;S,4.78;实测值:C,82.39;H,4.50;N,8.34;S,4.77;HRMS(ESI)m/z(M+):理论值:670.2160;实测值:670.2165。
实施例7
本实施例提供一种稠合多环化合物,化合物92的合成路径如下所示:
化合物92的制备方法具体包括以下步骤:
化合物N15的合成路径如下所示:
2)中间体2-92的合成:在三口瓶中加入化合物N15(75.1g,0.20mol),加入苯(500mL),无水三氯化磷(27.5g,0.2mol),氮气保护,回流16小时,冷却后,旋蒸除去苯后,加入无水三氯化铝(3.1g,0.02mol),反应混合物在180℃反应5小时,冷却后,柱层析纯化(PE:EA=5:1-3:1),得到中间体2-92(61.4g,产率69.8%)。
3)中间体3-92的合成:在三口瓶中加入中间体2-92(44.0g,0.10mol),加入无水四氢呋喃(300mL),氮气保护下,0℃下滴加苯基格式试剂(150mL,0.30mol),滴加完毕,在室温搅拌12小时,再回流2小时,冷却后,倒入冰水(300mL)中,加质量分数5%盐酸调pH值至中性,加二氯甲烷(200mL×2)萃取,有机相用饱和食盐水洗(200mL),硫酸钠干燥,旋干得到粗产品,粗产品再用乙醚:二氯甲烷(体积比1:1,400mL)重结晶,得到中间体3-92(31.1g,产率64.6%)。
4)化合物92的合成:在三口瓶中加入中间体3-92(9.6g,0.020mol),化合物N1(7.2g,0.030mol),叔丁醇钠(3.9g,0.040mol),xphos(400mg),二甲苯(60mL),抽氮气保护,再加入四(三苯基膦)钯(200mg),再抽氮气保护,升温至140℃搅拌4小时,降温,有机相旋干后,柱层析纯化(PE:EA=8:1-4:1)后,得到化合物92粗产物,粗产物用二甲苯、四氢呋喃各打浆三次后(80mL×6),得到化合物92(7.3g,产率53.2%)。
元素分析:(C46H27DN3PS)理论值:C,80.45;H,4.26;N,6.12;S,4.67;实测值:C,80.48;H,4.26;N,6.12;S,4.65;HRMS(ESI)m/z(M+):理论值:686.1804;实测值:686.1799。
实施例8
本实施例提供一种稠合多环化合物,化合物95的合成路径如下所示:
化合物95的制备方法具体包括以下步骤:
化合物N16的合成路径如下所示:
2)中间体2-95的合成:其合成方法同中间体2-92的合成,区别在于用化合物N16(75g,0.20mol)替代化合物N15,得中间体2-95(63.0g,产率71.8%)。
3)中间体3-95的合成:其合成方法同中间体3-92的合成,区别在于用中间体2-95(43.9g,0.1mol)替代中间体2-92,得中间体3-95(29.4g,产率61.2%)。
4)化合物95的合成:其合成方法同化合物92的合成,区别在于用中间体3-95(9.6g,0.02mol)替代中间体3-92,得化合物95(7.9g,产率57.8%)。
元素分析:(C47H27D3N3PS)理论值:C,80.32;H,4.73;N,5.98;S,4.56;实测值:C,80.36;H,4.72;N,5.96;S,4.55;HRMS(ESI)m/z(M+):理论值:702.2086;实测值:702.2091。
实施例9
本实施例提供一种稠合多环化合物,化合物111的合成路径如下所示:
化合物111的制备方法具体包括以下步骤:
1)中间体1-111的合成:在三口瓶中加入化合物N19(81.0g,0.20mol),N20(41.3g,0.24mol),碳酸钾(55.2g,0.40mol),四氢呋喃-水(四氢呋喃和水的体积比3:1,500mL),抽氮气保护,再加入四(三苯基膦)钯(2.0g),再抽氮气保护,升温至75℃搅拌4小时,降温萃取,有机相旋干后得到粗产品,柱层析纯化(PE:EA=10:1-5:1)后,得到中间体1-111(61g,产率75.1%)。
2)中间体2-111的合成:在醋酸(300mL)中加入中间体1-111(40.6g,0.10mol)加入铁粉(28g,0.50mol),室温搅拌2小时,过滤铁粉,醋酸旋干,得到粗产品50克,柱层析纯化(PE:EA=5:1-3:1)后,得到中间体2-111(34.7g,产率92.3%)。
3)中间体3-111的合成:三口瓶中加入中间体2-111(18.8g,0.05mol),苯基二氯化硼(9.5g,0.06mol),无水甲苯(150mL),三氯化铝(10.0g,0.08mol),氮气保护,甲苯回流4小时,冷却,过滤,滤液用饱和食盐水洗(100mL),旋干后,用甲苯打浆两次(100mL×2),得到中间体3-111(15.2g,66%)。
4)化合物111的合成:在三口瓶中加入中间体3-111(9.2g,0.020mol),化合物N1(7.22g,0.030mol),叔丁醇钠(3.9g,0.040mol),xphos(400mg),二甲苯(60mL),抽氮气保护,再加入四(三苯基膦)钯(200mg),再抽氮气保护,升温至140℃搅拌4小时,降温,有机相旋干后,柱层析纯化(PE:EA=4:1-2:1),得粗产物,粗产物用二甲苯、四氢呋喃各打浆三次后(80mL×6),得到产品化合物111(8.1g,产率60.6%)。
元素分析:(C46H27DBN3S)理论值:C,82.88;H,4.38;N,6.30;S,4.81;实测值:C,82.90;H,4.38;N,6.29;S,4.80;HRMS(ESI)m/z(M+):理论值:666.2160;实测值:666.2166。
实施例10
本实施例提供一种稠合多环化合物,化合物107的合成路径如下所示:
化合物107的制备方法具体包括以下步骤:
2)中间体1-107的合成:其合成方法同中间体1-111的合成,区别在于用化合物N17(77.8g,0.20mol)替代化合物N19,用化合物N18代化合物N20,得中间体1-107(56.8g,产率73.0%)。
3)中间体2-107的合成:其合成方法同中间体2-111的合成,区别在于用中间体1-107(38.9g,0.01mol)替代中间体1-111,得中间体2-107(33.5g,产率93.2%)。
4)中间体3-107的合成:其合成方法同中间体3-111的合成,区别在于用中间体2-107(18.0g,0.05mol)替代中间体2-111,得中间体3-107(14.9g,产率67%)。
5)化合物107的合成:其合成方法同化合物111的合成,区别在于用中间体3-107(8.9g,0.02mol)替代中间体3-111,得化合物107(8.2g,产率63.0%)。
元素分析:(C46H27DBN3O)理论值:C,84.93;H,4.49;N,6.46;实测值:C,84.97;H,4.49;N,6.45;HRMS(ESI)m/z(M+):理论值:650.2388;实测值:650.2393。
实施例11
本实施例提供一种稠合多环化合物,化合物133的合成路径如下所示:
化合物133的制备方法同化合物14,区别在于用中间体2替代中间体2-14,得化合物133,产率66%。
元素分析:C40H23N3S理论值:C,83.16;H,4.01;N,7.27;S,5.55;实测值:C,83.19;H,4.01;N,7.25;S,5.54;HRMS(ESI)m/z(M+):理论值:577.1613;实测值:577.1619。
器件实施例1
本实施例提供一种有机电致发光器件,包括从下向上依次层叠设置的阳极1、空穴注入层2、空穴传输层3、有机发光层4、电子传输层5、电子注入层6和阴极7,使所述器件形成如图1所示之具体结构:ITO/空穴注入层(HIL)(30nm)/空穴传输层(HTL)(40nm)/有机发光层(化合物10掺杂化合物RD)(40nm)/电子传输层(ETL)(40nm)/电子注入层(EIL/LiF)(1nm)/阴极(Al)(150nm);其中,
有机电致发光器件中阳极1选用ITO材料;
空穴注入层2材料选用如下所述结构的化合物HAT(CN)6:
空穴传输层3材料选用如下所述结构的化合物NPB:
有机发光层4以主体材料和客体材料共掺杂形成,其中主体材料选用化合物10,客体材料选用化合物RD,主体材料和客体材料掺杂的质量比为100:5;其中化合物RD的化学结构如下所示:
电子传输层5材料选用如下所述结构的化合物CBP:
电子注入层6材料由下述所示结构的化合物BCP与电子注入材料LiF掺杂形成:其中BCP与LiF掺杂的质量比为100:3:
阴极7选用金属Al。
上述有机电致发光器件的制备包括如下步骤:
1)基板清理:
将涂布了ITO透明电极的玻璃基板在商用清洗剂(横滨化学科技(常州)有限公司,成分与浓度为乙二醇类溶剂≤10wt%,三乙醇胺≤1wt%)中超声处理,在去离子水中冲洗,在丙酮:乙醇混合溶剂(体积比1:1)中超声除油,在洁净环境下烘烤至完全除去水份,然后用紫外光和臭氧清洗;
2)有机层和阴极的制备:
把上述带有阳极层的玻璃基板置于真空腔内,抽真空至1×10-6至2×10-4Pa,在上述阳极层膜上真空蒸镀HAT(CN)6作为空穴注入层,蒸镀速率为0.1nm/s,蒸镀厚度为30nm;
在空穴注入层上蒸镀空穴传输层,蒸镀速率为0.1nm/s,蒸镀膜厚为40nm;
在空穴传输层上蒸镀有机发光层,具体制备方法为:以共蒸的方式真空蒸镀发光主体材料和客体材料,主体材料蒸镀速率为0.1nm/s,客体材料蒸镀速率为0.005nm/s,蒸镀总膜厚为40nm;
在有机发光层上真空蒸镀一层电子传输层,蒸镀速率为0.1nm/s,蒸镀总膜厚为40nm;
在电子传输层上真空蒸镀一层电子注入层,其蒸镀速率为0.05nm/s,蒸镀总膜厚为1nm;
在电子注入层上蒸镀Al,其蒸镀速率为0.1nm/s,蒸镀总膜厚为150nm。
器件实施例2
本实施例提供一种有机电致发光器件,与器件实施例1中提供有机电致发光器件的区别在于:有机发光层中的主体材料选用化合物11。
器件实施例3
本实施例提供一种有机电致发光器件,与器件实施例1中提供有机电致发光器件的区别在于:有机发光层中的主体材料选用化合物14。
器件实施例4
本实施例提供一种有机电致发光器件,与器件实施例1中提供有机电致发光器件的区别在于:有机发光层中的主体材料选用化合物26。
器件实施例5
本实施例提供一种有机电致发光器件,与器件实施例1中提供有机电致发光器件的区别在于:有机发光层中的主体材料选用化合物74。
器件实施例6
本实施例提供一种有机电致发光器件,与器件实施例1中提供有机电致发光器件的区别在于:有机发光层中的主体材料选用化合物76。
器件实施例7
本实施例提供一种有机电致发光器件,与器件实施例1中提供有机电致发光器件的区别在于:有机发光层中的主体材料选用化合物92。
器件实施例8
本实施例提供一种有机电致发光器件,与器件实施例1中提供有机电致发光器件的区别在于:有机发光层中的主体材料选用化合物95。
器件实施例9
本实施例提供一种有机电致发光器件,与器件实施例1中提供有机电致发光器件的区别在于:有机发光层中的主体材料选用化合物111。
器件实施例10
本实施例提供一种有机电致发光器件,与器件实施例1中提供有机电致发光器件的区别在于:有机发光层中的主体材料选用化合物107。
器件实施例11
本实施例提供一种有机电致发光器件,与器件实施例1中提供有机电致发光器件的区别在于:有机发光层中的主体材料选用化合物133。
对比例1
本对比例提供一种有机电致发光器件,与器件实施例1中提供有机电致发光器件的区别在于:有机发光层中的主体材料选用化合物E-1。
对比例2
本对比例提供一种有机电致发光器件,与器件实施例1中提供有机电致发光器件的区别在于:有机发光层中的主体材料选用化合物E-2。
测试例1
1、测定热分解温度和玻璃化转变温度
化合物热分解温度的测定:使用热重分析仪(TGA美国TATGA55)对本专利材料进行热分解温度(Td)测试,测试范围室温至600℃,升温速率10℃/min,氮气氛围下,重量损失5%的温度定义为分解温度。
化合物玻璃化转变温度的测定:使用差示扫描量热仪(DSC,美国TADSC250)对本专利材料进行玻璃化转变温度(Tg)测试,测试范围室温至600℃,升温速率10℃/min,降温速度10℃/min,氮气氛围下,升降温循环两次。
2、LUMO和HOMO能级测试
使用电化学工作站利用循环伏安法(CV上海辰华CHI-600E)对本专利材料的HOMO与LUMO能级进行测试,以铂丝(Pt)为对电极,银/氯化银(Ag/AgCl)为参比电极。在氮气氛围下,在含有0.1M四丁基六氟磷酸铵的二氯甲烷电解液中以100mV/s的扫描速率进行测试,以二茂铁进行电位标定,设定二茂铁的电位在真空状态下的绝对能级为-4.8eV:
三线态能级测试条件:以甲苯作为溶剂,将待测试化合物配制成溶液(浓度2*10- 5mol/L),使用荧光分光光度计(日立F-4600)对上述溶液在-78℃条件下进行测试。其中ET1(eV)表示化合物的三线态能级,其用如下公式进行计算。
ET1=1240/λ
λ为最短紫外光/可见光吸收波长。
测试结果如表1所示。
表1
由表1中结果显示,本发明提供的稠合多环化合物拥有高的热分解温度,可以保证由其形成的主体材料在器件中保持优异的热稳定性,使得器件在制备过程中不易分解破坏;且本发明提供的稠合多环化合物的HOMO能级和LUMO能级与相邻的传输层相匹配,使OLED器件具有小的驱动电压,此外,本发明提供的稠合多环化合物的单线态能级高,能够保障主体材料向客体材料有效的能量传递。
测试例2
仪器:器件的电流、电压、亮度、寿命等特性采用PR 650光谱扫描亮度计和Keithley K 2400数字源表系统同步测试;
测试条件:电流密度为10mA/cm2,温度为25℃。
对器件实施例1-11和对比例1-2中的所提供的有机电致发光器件进行测试,结果如表2所示:
表2
对器件实施例1-11和对比例1-2中的所提供的有机电致发光器件进行测试,结果如表2所示,相比于对比例中的器件,本发明器件实施例所提供的OLED器件的工作电压更低、电流效率更高、器件的使用寿命更长,说明以本发明中提供的稠合多环化合物作为OLED器件的发光主体材料,能够显著提高器件的发光效率、降低器件的工作电压,延长器件的使用寿命,提升OLED的性能。值得注意的是,发明人在研究过程中发现,当本发明提供的稠合多环化合物结构中苯环在1、2位置处或2、3位置处或3、4位置处不与连接形成共有一边的稠环时,其器件的电流效率和器件寿命会受到严重的影响。
显然,上述实施例仅仅是为清楚地说明所作的举例,而并非对实施方式的限定。对于所属领域的普通技术人员来说,在上述说明的基础上还可以做出其它不同形式的变化或变动。这里无需也无法对所有的实施方式予以穷举。而由此所引伸出的显而易见的变化或变动仍处于本发明创造的保护范围之中。
Claims (12)
1.一种稠合多环化合物,其特征在于,具有如下所示的结构:
T1独立选自单键、NR15、S、O、BR15、PR15、C(R15)2,其中,R15相同或不同,并分别独立选自甲基、氘代甲基、苯基、氘代苯基、联苯基、氘代联苯基、萘基、氘代萘基;
T2和T3至少一个为单键,当T2为单键时,T3为S或O;当T3为单键时,T2为S或O;
R1-R14相同或不同,并分别独立选自氢、氘、甲基、氘代甲基、苯基、氘代苯基、氘代甲基取代苯基。
2.根据权利要求1所述的稠合多环化合物,其特征在于,R1-R14相同或不同,并至少一个选自氘、氘代甲基、氘代苯基、氘代甲基取代苯基中的一种。
3.根据权利要求1或2任一项所述的稠合多环化合物,其特征在于,R1-R4相同或不同,并至少含有一个氢;和/或,
R5-R8相同或不同,并至少含有一个氢;和/或,
R11-R14相同或不同,并至少含有一个氢。
4.根据权利要求1-3任一项所述的稠合多环化合物,其特征在于,当T2为单键时,T3为S或O;
优选的,当T2为单键时,T3为S。
7.一种如权利要求1-6任一项所述稠合多环化合物的制备方法,其特征在于,
当T1选自C(R15)2,即稠合多环化合物具有通式Ⅳ-1所示结构时,T4选自Cl C(R15)2或BrC(R15)2,其制备方法如下所示:
以式(E)所示的化合物为原料,在催化剂存在下经关环反应得到中间体化合物(F);中间体化合物(F)与式(G)所示的化合物在催化剂作用下经偶联反应得到通式Ⅳ-1所示化合物;
所述通式Ⅳ-1所示化合物的制备路径如下所示:
或当T1选自BR15,即稠合多环化合物具有通式Ⅳ-2所示结构时,T4选自氢,其制备方法如下所示:
以式(E)所示的化合物为原料,与式(H)所示的化合物在催化剂存在下反应得到中间体化合物(J);中间体化合物(J)与式(G)所示的化合物在催化剂作用下经偶联反应得到通式Ⅳ-2所示化合物;
所述通式Ⅳ-2所示化合物的制备路径如下所示:
或当T1选自O,即稠合多环化合物具有通式Ⅳ-3所示结构时,T4选自羟基,其制备方法如下所示:
以式(E)所示的化合物为原料,在催化剂存在下反应得到中间体化合物(K);中间体化合物(K)与式(G)所示的化合物在催化剂作用下经偶联反应得到通式Ⅳ-3所示化合物;
所述通式Ⅳ-3所示化合物的制备路径如下所示:
或当T1选自S,即稠合多环化合物具有通式Ⅳ-4所示结构时,T4选自巯基,其制备方法如下所示:
以式(E)所示的化合物为原料,在催化剂存在下反应得到中间体化合物(K-1);中间体化合物(K-1)与式(G)所示的化合物在催化剂作用下经偶联反应得到通式Ⅳ-4所示化合物;
所述通式Ⅳ-4所示化合物的制备路径如下所示:
或当T1选自PR15,即稠合多环化合物具有通式Ⅳ-5所示结构时,T4选自氢,其制备方法如下所示:
以式(E)所示的化合物为原料,在催化剂存在下反应得到中间体化合物(L);中间体化合物(L)在催化剂的作用下反应得到中间体化合物(M),中间体化合物(M)与式(N)所示的化合物在催化剂作用下经偶联反应得到中间体化合物(O),中间体化合物(O)与式(G)所示的化合物在催化剂作用下经偶联反应得到通式Ⅳ-5所示化合物;
所述通式Ⅳ-5所示化合物的制备路径如下所示:
或当T1选自NR15,即稠合多环化合物具有通式Ⅳ-6所示结构时,T4选自硝基,其制备方法如下所示:
以式(D)所示的化合物为原料,在催化剂存在下反应得到中间体化合物(P);中间体化合物(P)与式(Q)所示的化合物、式(G)所示的化合物相继反应得到通式Ⅳ-6所示化合物;
所述通式Ⅳ-6所示化合物的制备路径如下所示:
或当T1选自单键,即稠合多环化合物具有通式Ⅳ-7所示结构时,其制备方法如下所示:
以式(R)所示的化合物为原料,与式(S)所示的化合物在催化剂的作用下反应得到中间体化合物(T),中间体化合物(T)在催化剂的作用下关环反应得到中间体化合物(U),中间体化合物(U)与式(G)所示的化合物在催化剂作用下经偶联反应得到通式Ⅳ-7所示化合物;
所述通式Ⅳ-7所示化合物的制备路径如下所示:
W选自氟、氯、溴或碘。
9.一种电子器件,其特征在于,所述电子器件中包含权利要求1-6任一项所述的稠合多环化合物中的任意一种或至少两种组合;
优选的,所述电子器件为有机电致发光器件、有机场效应晶体管、有机薄膜晶体管、有机发光晶体管、有机集成电路、有机太阳能电池、有机场淬灭器件、发光电化学电池、有机激光二极管或有机光感受器中的任意一种。
10.根据权利要求9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阳极和阴极,以及位于阳极和阴极之间的有机薄膜层,所述有机薄膜层包括权利要求1-6任一项所述的稠合多环化合物中的任意一种或至少两种组合;
优选的,所述有机薄膜层包括发光层,还包括空穴注入层、空穴传输层、空穴阻挡层、电子传输层、电子注入层、电子阻挡层和电荷传输层中的任意一种或至少两种组合,所述发光层中包含权利要求1-6任一项所述的稠合多环化合物中的任意一种或至少两种组合;
优选的,所述发光层包括主体材料和客体材料;所述发光层中的主体材料包含权利要求1-6任一项所述的稠合多环化合物中的任意一种或至少两种组合。
11.一种显示装置,其特征在于,所述显示装置包括权利要求9或10所述的电子器件。
12.一种照明装置,其特征在于,所述照明装置包括权利要求9或10所述的电子器件。
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CN107922311A (zh) * | 2016-04-26 | 2018-04-17 | 德山新勒克斯有限公司 | 有机电气元件用化合物、利用其的有机电气元件及其电子装置 |
US20190135730A1 (en) * | 2016-04-26 | 2019-05-09 | Duk San Neolux Co., Ltd. | Compound for organic electric element, organic electric element using same, and electronic device comprising same organic electronic element |
WO2017204556A1 (ko) * | 2016-05-26 | 2017-11-30 | 덕산네오룩스 주식회사 | 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
WO2018026197A1 (ko) * | 2016-08-03 | 2018-02-08 | 덕산네오룩스 주식회사 | 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
KR20180015546A (ko) * | 2016-08-03 | 2018-02-13 | 덕산네오룩스 주식회사 | 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
KR20190075322A (ko) * | 2017-12-21 | 2019-07-01 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
WO2020032428A1 (ko) * | 2018-08-09 | 2020-02-13 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물을 포함하는 유기전기소자 및 그 전자 장치 |
WO2020032447A1 (ko) * | 2018-08-09 | 2020-02-13 | 덕산네오룩스 주식회사 | 이종 화합물의 혼합물을 호스트로 포함하는 유기전기소자 및 그 전자 장치 |
WO2020032424A1 (ko) * | 2018-08-09 | 2020-02-13 | 덕산네오룩스 주식회사 | 이종 화합물의 혼합물을 호스트로 포함하는 유기전기소자 및 그 전자 장치 |
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US11626562B2 (en) | 2023-04-11 |
KR102422398B1 (ko) | 2022-07-19 |
KR102422420B1 (ko) | 2022-07-19 |
KR20200126889A (ko) | 2020-11-09 |
US20200343456A1 (en) | 2020-10-29 |
US11706982B2 (en) | 2023-07-18 |
KR20200126890A (ko) | 2020-11-09 |
JP2020183372A (ja) | 2020-11-12 |
CN111233888A (zh) | 2020-06-05 |
US20200343455A1 (en) | 2020-10-29 |
CN110330506A (zh) | 2019-10-15 |
JP7022446B2 (ja) | 2022-02-18 |
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JP2020183371A (ja) | 2020-11-12 |
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