CN115703779A - 一种含氮稠杂环化合物及其应用 - Google Patents
一种含氮稠杂环化合物及其应用 Download PDFInfo
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- CN115703779A CN115703779A CN202110915286.6A CN202110915286A CN115703779A CN 115703779 A CN115703779 A CN 115703779A CN 202110915286 A CN202110915286 A CN 202110915286A CN 115703779 A CN115703779 A CN 115703779A
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- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
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- 230000005525 hole transport Effects 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
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Abstract
本发明提供一种含氮稠杂环化合物及其应用,本发明所述含氮稠杂环化合物用作发光层主体材料时,能够使得有机发光器件具有更低的驱动电压(4.3V以下),更高的电流效率(16Cd/A以上)和更长的寿命(230h以上)。
Description
技术领域
本发明属于化合物制备技术领域,涉及一种含氮稠杂环化合物及其应用。
背景技术
近来,作为图像显示装置的有机电致发光显示器的开发正在积极地进行。与液晶显示装置等不同,有机电致发光显示器是自发光显示装置,其中从第一电极和第二电极注入的空穴和电子在发射层中复合,并且因此发射层中的包括有机化合物的发光材料发射光以实现图像的显示。
目前为止,基于荧光和磷光的发光材料体系已被开发出来,使用荧光材料的有机发光二极管具有可靠性高的特点,但其在电气激发下其内部电致发光量子效率被限制为25%,这是因为激子的单重激发态和三重激发态的分支比为1:3。与此相反,使用磷光材料的有机发光二极管已经取得了几乎100%的内部电致发光量子效率。然而,磷光OLED的稳定性还需提高。而OLED的稳定性,除了发光体本身,主体材料是关键。
对于红、绿光磷光发光器件,主体材料性能决定红、绿磷光发光器件效率及寿命,当前常用的主体材料为一类含咔唑基团的有机化合物,但该类材料存在电荷传输不平衡等缺点,同时这类材料的稳定性有限,导致器件寿命不高。
因此,在本领域,开发具有高性能主体材料至关重要。
发明内容
针对现有技术的不足,本发明的目的在于提供一种含氮稠杂环化合物及其应用。
为达此目的,本发明采用以下技术方案:
一方面,本发明提供一种含氮稠杂环化合物,所述含氮稠杂环化合物具有式(1)所示结构:
其中,
Ar、Ar1各自独立选自取代或未取代的C6-C60芳基、取代或未取代的C3-C60的杂芳基,
L、L1各自独立选自连接键、取代或未取代的C6-C30的亚芳基、取代或未取代的C3-C30的亚杂芳基,
R1-R4各自独立选自氢、氘、卤素、氰基、取代或未取代的C1-C30烷基、取代或未取代的C7-C30芳烷基、取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基、取代或未取代的C4-C30杂芳烷基、取代或未取代的C3-C30环烷基、取代或未取代的C3-C30杂环烷基、取代或未取代的C3-C30环烯基、取代或未取代的C1-C30烷氧基或取代或未取代的C6-C30芳氧基,
R1-R4各自独立存在或相邻两者连接成环A,所述环A为C6-C30的芳环,优选苯环。
在本发明中,所述含氮稠杂环化合物的电子空穴传输能力平衡,所制备器件的电流效率和寿命均有显著提升。
Y选自O或S,
RY选自取代或未取代的C6-C30的亚芳基、取代或未取代的C3-C30的亚杂芳基,
R5-R12各自独立选自氢、氘、卤素、氰基、取代或未取代的C1-C30烷基、取代或未取代的C1-C30烷基、其中一个或多个亚甲基以O原子或S原子不相邻的方式被-O-或-S-取代的C1-C30烷基、取代或未取代的C2-C30烯基、其中一个或多个亚甲基以O原子或S原子不相邻的方式被-O-或-S-取代的C2-C30烯基、取代或未取代的C2-C30炔基、取代或未取代的C7-C30芳烷基、取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基、取代或未取代的C4-C30杂芳烷基、取代或未取代的C3-C30环烷基、取代或未取代的C3-C30杂环烷基、取代或未取代的C3-C30环烯基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C30芳氧基、取代或未取代的C6-C60芳胺基、取代或未取代的C5-C60的杂芳胺基、取代或未取代的C5-C60的芳基杂芳胺基,
R5-R12各自独立存在或相邻二者至四者连接成环B,所述环B为取代或未取代的C6-C30的芳环、取代或未取代的C5-C30的杂芳环。
优选地,所述环B为取代或未取代的苯环、取代或未取代的萘环、取代或未取代的吲哚环、取代或未取代的茚环、取代或未取代的苯并呋喃环、取代或未取代的苯并噻吩环、取代或未取代的苯并吲哚环、取代或未取代的萘并吲哚环。
优选地,Ar选自取代或未取代的如下基团:
优选地,Ar1选自取代或未取代的如下基团:苯基、联苯基、三联苯基、萘基、苯基取代萘基、萘基取代苯基、蒽基、菲基、苯并菲基、吡啶基、二苯并呋喃基、二苯并噻吩基、咔唑基、苯基取代咔唑基、吡啶基取代咔唑基、萘基取代咔唑基、联苯基取代咔唑基、二苯并呋喃取代苯基、二苯并噻吩取代苯基、二甲基芴基、二苯基取代芴基、螺二芴基、苯并萘并呋喃基、苯并萘并噻吩基、苯并咔唑基或二苯并咔唑基。
优选地,L选自取代或未取代的如下基团:亚苯基、亚联苯基、亚萘基,
优选地,L1选自连接键、取代或未取代的如下基团:亚苯基、亚联苯基、亚萘基。
优选地,所述含氮稠杂环化合物为如下化合物中的任意一种:
本发明所述烷基可以为直链及支链中的任一种,可选的,所述烷基包括但不限于甲基、乙基、丙基、异丙基、丁基、2-丁基、异丁基、叔丁基。
本发明所述环烷基包括但不限于环丙烷、环丁烷、环己烷。
本发明所述烯基是指衍生自具有一个或多个碳-碳双键并具有2至40个碳原子的直链或支链不饱和烃的单价取代基。其实例包括但不限于乙烯基、烯丙基、异丙烯基、2-丁烯基等。
本发明所述芳基包括单环、多环、稠环类芳基,所述环之间可以被短的非芳族单元(例如亚甲基)所间断。所述芳基选自苯基、联苯基、联三苯基、萘基、联萘基、苯基萘基、萘基苯基、芴基、苯基芴基、苯并芴基、二苯并芴基、菲基、苯基菲基、蒽基、茚基、亚三苯基、芘基、并四苯基、苝基、屈基、稠四苯基、荧蒽基或螺二芴基。
本发明所述杂芳基包括单环、多环、稠环类,所述环之间可以被短的非芳族单元(例如亚甲基、O、S、N)所间断。所述杂芳基选自呋喃基、苯硫基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、异噻唑基、异噁唑基、噁唑基、噁二唑基、三嗪基、四嗪基、三唑基、四唑基、呋吖基、吡啶基、吡嗪基、嘧啶基、哒嗪基、苯并呋喃基、苯并噻吩基、异苯并呋喃基、二苯并呋喃基、二苯并噻吩基、苯并咪唑基、苯并噻唑基、苯并异噻唑基、苯并异噁唑基、苯并噁唑基、异吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、异喹啉基、噌啉基、喹唑啉基、喹喔啉基、咔唑基、吩噁嗪基、吩噻嗪基、菲啶基、苯并间二氧杂环戊烯基或二氢吖啶基。
在本发明中,基团的限定中限定了碳原子数的范围,其碳原子数为所限定范围内的任一整数,例如C6-C60芳基,代表芳基的碳原子数可以是6-60所包含的范围内的任意整数,例如6、8、10、15、20、30、35、40、45、50、55或60等。
在本发明中,所述具有式(1)所示结构的化合物的合成通式如下:
另一方面,本发明提供了如上所述含氮稠杂环化合物在制备光学器件中的应用。
优选地,所述光学器件包括有机电致发光器件、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任意一种。
另一方面,本发明提供一种有机电致发光器件,所述有机电致发光器件包括阳极和阴极,和设置在阳极和阴极间的有机层,所述有机层包括如上所述的含氮稠杂环化合物中的任意一种或至少两种的组合。
优选地,所述有机层包括从阳极侧到阴极侧依次层叠设置的空穴注入层、空穴传输层、发光层、电子传输层和电子注入层。
优选地,所述发光层的材料包含主体材料和客体材料,所述主体材料包含如上所述的含氮稠杂环化合物中的任意一种或至少两种的组合。
优选地,所述客体材料包括磷光掺杂剂,所述磷光掺杂剂包括含Ir、Os或Pt的配合物。
另一方面,本发明提供一种有机电致发光设备,所述有机电致发光设备包括如上所述的有机电致发光器件。
相对于现有技术,本发明具有以下有益效果:
本发明的含氮稠杂环化合物或用作发光层主体材料时,能够使得有机发光器件具有更低的驱动电压(4.3V以下),更高的电流效率(16Cd/A以上)和更长的寿命(230h以上)。
具体实施方式
下面通过具体实施方式来进一步说明本发明的技术方案。本领域技术人员应该明了,所述实施例仅仅是帮助理解本发明,不应视为对本发明的具体限制。
制备实施例
(1)1-B的合成:在50毫升三颈瓶中,加入1-A(1mmol),水合肼(15毫升),60摄氏度搅拌反应2小时,反应结束后,加水淬灭,二氯甲烷萃取,旋转蒸发除去溶剂,得1-B。
(2)1-C的合成:在50毫升三颈瓶中,加入步骤(1)中的产物,2-溴苯甲醛(1mmol),乙醇(20毫升),90摄氏度搅拌反应5小时,反应结束后加水淬灭,二氯甲烷萃取,无水硫酸镁干燥,过滤得有机相,旋转蒸发除去溶剂,粗产物用柱层析分离(乙酸乙酯:正己烷=1:10(体积比))得1-C(0.28克,产率70%)。
(3)1-D的合成:在50毫升三颈瓶中,加入1-C(1mmol),碘苯二乙酸(2mmol),二氯甲烷(20毫升),室温搅拌反应6小时,反应结束后除去溶剂,用柱层析分离(乙酸乙酯:正己烷=1:10(体积比)),得1-D(0.26克,产率65%)。
(4)1-F的合成:在50毫升三颈瓶中,加入1-D(1mmol),碳酸钾(2mmol),1,2-二氯苯(20毫升),190摄氏度搅拌反应3小时,反应结束后除去溶剂,粗产物用柱层析分离(乙酸乙酯:正己烷=1:10(体积比)),得1-F(0.31克,产率78%)。
(5)化合物1的合成:在50毫升双颈圆底烧瓶中,干燥后充入氮气,分别加入1-F(1mmol)、1-G(1mmol)、碳酸铯(0.012mol)、三(二亚苄基丙酮)二钯(Pd2(dba)3,0.05mmol)和2-二环己基磷-2′,4′,6′-三异丙基联苯(xphos,0.055mmol),然后加入甲苯,混合物回流24小时,反应后冷却至室温,反应体系过滤后浓缩,粗产物以层析纯化(二氯甲烷/正己烷=1:10(体积比)),得化合物1(0.5克,产率82%)。
HRMS-ESI m/z[M+H]+:612.24。
元素分析:C43H25N5理论值:C,84.43;H,4.12;N,11.45;实测值:C,84.49;H,4.10;N,11.41。
(1)2-C的合成:同1-C的合成,间溴苯甲醛替代2-溴苯甲醛,得2-C(0.27克,产率68%)。
(2)2-D的合成:同1-D的合成,区别在于用2-C替代1-C,得2-D(0.27克,产率68%)。
(3)2-F的合成:同1-F的合成,区别在于用2-D替代1-D,得2-F(0.3克,产率75%)。
(4)化合物2的合成:同化合物1的合成,区别在于用2-F替代1-F,2-G替代1-G,得化合物2(0.56克,产率86%)。
HRMS-ESI m/z[M+H]+:654.24。
元素分析:C44H27N7理论值:C,80.84;H,4.16;N,15.00;实测值:C,80.77;H,4.18;N,15.05。
(1)3-B的合成:同1-B的合成,区别在于用3-A替代1-A,得3-B。
(2)3-C的合成:同1-C的合成,区别在于用3-B替代1-B,得3-C(0.33克,产率67%)。
(3)3-D的合成:同1-D的合成,区别在于用3-C替代1-C,得3-D(0.31克,产率63%)。
(4)3-F的合成:同1-F的合成,区别在于用3-D替代1-D,得3-F(0.38克,产率78%)。
(5)化合物3的合成:同化合物1的合成,区别在于用3-F替代1-F,得化合物3(0.55克,产率78%)。
HRMS-ESI m/z[M+H]+:702.23。
元素分析:C49H27N5O理论值:C,83.86;H,3.88;N,9.98;实测值:C,83.84;H,3.87;N,10.01。
(1)4-B的合成:同1-B的合成,区别在于用4-A替代1-A,得4-B。
(2)4-C的合成:同1-C的合成,区别在于用4-B替代1-B,间溴苯甲醛替代2-溴苯甲醛,得4-C(0.35克,产率67%)。
(3)4-D的合成:同1-D的合成,区别在于用4-C替代1-C,得4-D(0.36克,产率69%)。
(4)4-F的合成:同1-F的合成,区别在于用4-D替代1-D,得4-F(0.40克,产率77%)。
(5)化合物4的合成:同化合物1的合成,区别在于用4-F替代1-F,4-G替代1-G,得化合物4(0.66克,产率87%)。
HRMS-ESI m/z[M+H]+:760.26。
元素分析:C52H33N5S理论值:C,82.19;H,4.38;N,9.22;S,4.22;实测值:C,82.21;H,4.40;N,9.19;S,4.20;。
(1)5-C的合成:同1-C的合成,区别在于用4-溴-3-甲基苯甲醛替代2-溴苯甲醛,得5-C(0.27克,产率64%)。
(2)5-D的合成:同1-D的合成,区别在于用5-C替代1-C,得5-D(0.27克,产率65%)。
(3)5-F的合成:同1-F的合成,区别在于用5-D替代1-D,得5-F(0.33克,产率80%)。
(4)化合物5的合成:同化合物1的合成,区别在于用5-F替代1-F,得化合物5(产率88%)。
HRMS-ESI m/z[M+H]+:626.20。
元素分析:C44H27N5理论值:C,84.46;H,4.35;N,11.19;实测值:C,84.42;H,4.37;N,11.21。
(1)6-B的合成:同1-B的合成,区别在于用6-A替代1-A,得6-B。
(2)6-C的合成:同1-C的合成,区别在于用6-B替代1-B,得6-C(0.3克,产率70%)。
(3)6-D的合成:同1-D的合成,区别在于用6-C替代1-C,得6-D(0.29克,产率67%)。
(4)6-F的合成:同1-F的合成,区别在于用6-D替代1-D,得6-F(0.33克,产率77%)。
(5)化合物6的合成:同化合物1的合成,区别在于用6-F替代1-F,得化合物6(0.5克,产率78%)。
HRMS-ESI m/z[M+H]+:637.18。
元素分析:C44H24N6理论值:C,83.00;H,3.80;N,13.20;实测值:C,83.03;H,3.81;N,13.16。
(1)化合物7的合成:在50毫升三颈瓶,加入2-F(1mmol),原料7-G(1mmol),碳酸钾(1.2mmol),四(三苯基膦)钯(0.05mmol),甲苯(10毫升),水(3毫升),60℃反应10小时,反应完成后冷却至室温,加入3毫升冰水淬灭,二氯甲烷(10×3毫升)萃取,所得到的萃取液依序加入硫酸镁干燥、过滤及旋干,粗产物以层析纯化(乙酸乙酯/正己烷,1/10(体积比)),得化合物7(0.43克,产率69%)。
HRMS-ESI m/z[M+H]+:625.25。
元素分析:C45H28N4理论值:C,86.51;H,4.52;N,8.97;实测值:C,86.47;H,4.54;N,8.99。
(1)化合物8的合成:同化合物7的合成,区别在于用1-F替代2-F,8-G替代7-G,得化合物8(0.48克,产率76%)
HRMS-ESI m/z[M+H]+:632.21。
元素分析:C42H25N5S理论值:C,79.85;H,3.99;N,11.09;S,5.07;实测值:C,79.85;H,3.98;N,11.12;S,5.05。
(1)化合物9的合成:同化合物7的合成,区别在于用4-F替代2-F,9-G替代7-G,得化合物9(0.55克,产率73%)
HRMS-ESI m/z[M+H]+:753.30。
元素分析:C55H36N4理论值:C,87.74;H,4.82;N,7.44;实测值:C,87.78;H,4.81;N,7.41。
(1)化合物10的合成:同化合物1的合成,区别在于用2-F替代1-F,10-G替代1-G,得化合物10(产率85%)
HRMS-ESI m/z[M+H]+:651.19。
元素分析:C45H26N6理论值:C,83.06;H,4.03;N,12.91;实测值:C,83.11;H,4.03;N,12.86。
器件实施例1
提供一种有机电致发光器件,包括层叠设置在基板上的阳极(ITO)、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层和阴极;制备方法如下:
(1)基板清理:将涂布了ITO的玻璃基板在水性清洗剂中超声处理,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)蒸镀空穴注入层:把上述带有阳极层的玻璃基板置于真空腔内,抽真空至1×10-6~2×10-4Pa,在上述阳极层膜上真空蒸镀NDP-9作为空穴注入层,蒸镀厚度为5nm;
在空穴注入层上再蒸镀H作为第二空穴注入层10nm;
(3)蒸镀空穴传输层:在空穴注入层上蒸镀HT作为空穴传输层,蒸镀膜厚为80nm;
(4)蒸镀发光层:在空穴传输层上以共蒸的方式真空蒸镀本发明提供的化合物1(主体材料)和客体材料(piq)2Ir(acac),主体材料与客体材料的质量比为95:5,蒸镀总膜厚为30nm;
(5)蒸镀电子传输层:在发光层上以共蒸的方式真空蒸镀ET1和LiQ(质量比为1:1),蒸镀总膜厚为30nm;
(6)蒸镀电子注入层:在电子传输层上真空蒸镀LiQ作为电子注入层,蒸镀总膜厚为1nm;
(7)阴极:在电子注入层上蒸镀Mg:Ag(质量比为9:1)作为阴极,蒸镀膜厚为20nm;得到所述有机电致发光器件。
器件实施例2-10、对比例1
一种有机电致发光器件,其与实施例1的区别仅在于,将发光层的主体材料替换为表2中的器件实施例2-10、对比例1分别对应的化合物。
以上实施例、对比例中涉及的材料结构如下:
性能测试:
以上实施例和对比例提供的有机电致发光器件的电流、电压、亮度等特性采用PR650光谱扫描亮度计和Keithley K 2400数字源表系统同步测试;
电光特性测试条件:电流密度为10mA/cm2,室温;
寿命测试:电流密度为20mA/cm2,室温,器件亮度下降至原始亮度的95%时记录时间(以小时计),测试结果如表2所示。
表2
由表2可以看出,本发明的化合物使得有机电致发光器件具有更低的驱动电压(4.3V以下),更高的电流效率(16Cd/A以上)和更长的寿命(230h以上)。
申请人声明,本发明通过上述实施例来说明本发明的含氮稠杂环化合物及其应用,但本发明并不局限于上述实施例,即不意味着本发明必须依赖上述实施例才能实施。所属技术领域的技术人员应该明了,对本发明的任何改进,对本发明产品各原料的等效替换及辅助成分的添加、具体方式的选择等,均落在本发明的保护范围和公开范围之内。
Claims (10)
1.一种含氮稠杂环化合物,其特征在于,所述含氮稠杂环化合物具有式(1)所示结构:
其中,
Ar、Ar1各自独立选自取代或未取代的C6-C60芳基、取代或未取代的C3-C60的杂芳基,
L、L1各自独立选自连接键、取代或未取代的C6-C30的亚芳基、取代或未取代的C3-C30的亚杂芳基,
R1-R4各自独立选自氢、氘、卤素、氰基、取代或未取代的C1-C30烷基、取代或未取代的C7-C30芳烷基、取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基、取代或未取代的C4-C30杂芳烷基、取代或未取代的C3-C30环烷基、取代或未取代的C3-C30杂环烷基、取代或未取代的C3-C30环烯基、取代或未取代的C1-C30烷氧基或取代或未取代的C6-C30芳氧基,
R1-R4各自独立存在或相邻两者连接成环A,所述环A为C6-C30的芳环,优选苯环。
Y选自O或S,
RY选自取代或未取代的C6-C30的亚芳基、取代或未取代的C3-C30的亚杂芳基,
R5-R12各自独立选自氢、氘、卤素、氰基、取代或未取代的C1-C30烷基、取代或未取代的C1-C30烷基、其中一个或多个亚甲基以O原子或S原子不相邻的方式被-O-或-S-取代的C1-C30烷基、取代或未取代的C2-C30烯基、其中一个或多个亚甲基以O原子或S原子不相邻的方式被-O-或-S-取代的C2-C30烯基、取代或未取代的C2-C30炔基、取代或未取代的C7-C30芳烷基、取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基、取代或未取代的C4-C30杂芳烷基、取代或未取代的C3-C30环烷基、取代或未取代的C3-C30杂环烷基、取代或未取代的C3-C30环烯基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C30芳氧基、取代或未取代的C6-C60芳胺基、取代或未取代的C5-C60的杂芳胺基、取代或未取代的C5-C60的芳基杂芳胺基,
R5-R12各自独立存在或相邻二者至四者连接成环B,所述环B为取代或未取代的C6-C30的芳环、取代或未取代的C3-C30的杂芳环;
优选地,所述环B为取代或未取代的苯环、取代或未取代的萘环、取代或未取代的吲哚环、取代或未取代的茚环、取代或未取代的苯并呋喃环、取代或未取代的苯并噻吩环、取代或未取代的苯并吲哚环、取代或未取代的萘并吲哚环。
4.根据权利要求1-3中任一项所述的含氮稠杂环化合物,其特征在于,Ar1选自取代或未取代的如下基团:苯基、联苯基、三联苯基、萘基、苯基取代萘基、萘基取代苯基、蒽基、菲基、苯并菲基、吡啶基、二苯并呋喃基、二苯并噻吩基、咔唑基、苯基取代咔唑基、吡啶基取代咔唑基、萘基取代咔唑基、联苯基取代咔唑基、二苯并呋喃取代苯基、二苯并噻吩取代苯基、二甲基芴基、二苯基取代芴基、螺二芴基、苯并萘并呋喃基、苯并萘并噻吩基、苯并咔唑基或二苯并咔唑基;
优选地,L选自取代或未取代的如下基团:亚苯基、亚联苯基、亚萘基,
优选地,L1选自连接键、取代或未取代的如下基团:亚苯基、亚联苯基、亚萘基。
6.根据权利要求1-5中任一项所述的含氮稠杂环化合物在制备光学器件中的应用。
7.根据权利要求6所述的应用,其特征在于,所述光学器件包括有机电致发光器件、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任意一种。
8.一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阳极和阴极,和设置在阳极和阴极间的有机层,所述有机层包括如权利要求1-5中任一项所述的含氮稠杂环化合物中的任意一种或至少两种的组合。
9.根据权利要求8所述的有机电致发光器件,其特征在于,所述有机层包括从阳极侧到阴极侧依次层叠设置的空穴注入层、空穴传输层、发光层、电子传输层和电子注入层;
优选地,所述发光层的材料包含主体材料和客体材料,所述主体材料包含如权利要求1-5中任一项所述的含氮稠杂环化合物中的任意一种或至少两种的组合;
优选地,所述客体材料包括磷光掺杂剂,所述磷光掺杂剂包括含Ir、Os或Pt的配合物。
10.一种有机电致发光设备,其特征在于,所述有机电致发光设备包括如权利要求8或9所述的有机电致发光器件。
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- 2022-08-09 DE DE102022120042.6A patent/DE102022120042A1/de active Pending
- 2022-08-09 US US17/884,199 patent/US20230111454A1/en active Pending
- 2022-08-09 KR KR1020220099465A patent/KR20230023591A/ko unknown
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WO2018080068A1 (ko) * | 2016-10-27 | 2018-05-03 | 주식회사 두산 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
CN112300052A (zh) * | 2019-07-23 | 2021-02-02 | 北京鼎材科技有限公司 | 一种化合物及其应用、包含其的有机电致发光器件 |
Non-Patent Citations (1)
Title |
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STN: "CAS RN 2600756-88-3 & 2600757-71-7", pages 1 - 13, Retrieved from the Internet <URL:https://www.stn.org> * |
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JP2023025696A (ja) | 2023-02-22 |
US20230111454A1 (en) | 2023-04-13 |
DE102022120042A1 (de) | 2023-02-16 |
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