CN116621836A - 一种咔唑衍生物及其应用 - Google Patents
一种咔唑衍生物及其应用 Download PDFInfo
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- CN116621836A CN116621836A CN202310591706.9A CN202310591706A CN116621836A CN 116621836 A CN116621836 A CN 116621836A CN 202310591706 A CN202310591706 A CN 202310591706A CN 116621836 A CN116621836 A CN 116621836A
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- substituted
- unsubstituted
- aryl
- carbazole derivative
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- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title claims abstract description 49
- -1 carbazole dinaphthol indole Chemical compound 0.000 claims abstract description 105
- 239000000463 material Substances 0.000 claims abstract description 43
- 239000010410 layer Substances 0.000 claims description 129
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 14
- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 12
- 125000005264 aryl amine group Chemical group 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000005605 benzo group Chemical group 0.000 claims description 9
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- 125000005842 heteroatom Chemical group 0.000 claims description 9
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- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 7
- 125000001041 indolyl group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
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- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- BZHGXQBPJUHVFW-UHFFFAOYSA-N toluene;tritert-butylphosphane Chemical compound CC1=CC=CC=C1.CC(C)(C)P(C(C)(C)C)C(C)(C)C BZHGXQBPJUHVFW-UHFFFAOYSA-N 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DETFWTCLAIIJRZ-UHFFFAOYSA-N triphenyl-(4-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DETFWTCLAIIJRZ-UHFFFAOYSA-N 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
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Abstract
本发明涉及有机电致发光材料技术领域,尤其涉及一种咔唑衍生物及其应用。本发明所述的咔唑衍生物具有咔唑连萘并吲哚的新颖结构,具有输送电子和空穴的双极性,适宜作为有机电致发光元件用材料使用;含有所述咔唑衍生物的有机电致发光元件用材料,具有启动电压低,发光效率和亮度高的特点。另外,本发明的咔唑衍生物具有良好的热稳定性和成膜性能,应用在有机电致发光元件用材料、有机电致发光元件、显示装置、照明装置中,能够延长使用寿命,从而能够降低功耗和制造成本。
Description
技术领域
本发明涉及有机电致发光材料技术领域,尤其涉及一种咔唑衍生物及其在有机电致发光元件、显示装置和照明装置中的应用。
背景技术
最近几年有机电致发光显示技术已趋于成熟,一些产品已进入市场,但在产业化过程中,仍有许多问题亟待解决,特别是用于制作元件的各种有机材料,其载流子注入、传输性能,材料电发光性能、使用寿命、色纯度、各种材料之间及与各电极之间的匹配等,尚有许多问题还未解决。尤其是发光元件在发光效率和使用寿命方面还达不到实用化要求,这大大限制了OLED技术的发展。
有机电致发光主要分为荧光和磷光,但根据自旋量子统计理论,单重态激子和三重态激子的概率为1:3,即来自单重态激子辐射跃迁的荧光的理论极限为25%,三重态激子辐射跃迁的荧光的理论极限为75%。如何利用75%的三线态激子的能量成为当务之急。1997年Forrest等发现磷光电致发光现象突破了有机电致发光材料量子效率25%效率的限制,引起人们对金属配合物磷光材料的广泛关注。从此,人们对磷光材料进行大量的研究。
鉴于以上原因,特提出本发明。
发明内容
为了解决现有技术存在的以上问题,本发明提供了一种咔唑衍生物及其应用,将该咔唑衍生物作为有机电致发光元件用材料的原料,能够提供启动电压降低、发光效率高、亮度提高的有机电致发光元件用材料以及有机电致发光元件。
为了实现上述目的,本发明采用如下技术方案:
本发明提供一种咔唑衍生物,其结构如式(I)所示:
其中,
R1、R2、R3、R4、R5、R6、R7、R8、R9各自独立地选自由氢、氘、腈基、卤原子、取代或未取代的C1~C40直链烷基、取代或未取代的C1~C40直链杂烷基、取代或未取代的C3~C40支链或环状的烷基、取代或未取代的C3~C40支链或环状的杂烷基、取代或未取代的C2~C40烯基或炔基、取代或未取代的C6~C60芳基、取代或未取代的C6~C60芳基胺基、取代或未取代的C2~C60杂芳基、或*-L2NAr2Ar3组成的群组,R1~R9中的两个或更多个相邻的取代基团可以任意地接合或稠合形成取代或未取的环;
L1、L2各自独立地选自由单键、取代或未取代的C6~C60亚芳基、取代或未取代的C2~C60亚杂芳基组成的群组;
m表示0~5的整数;
Ar1、Ar2、Ar3各自独立地选自由取代或未取代的C6~C60芳基、取代或未取代的C6~C60芳基胺基、取代或未取代的C2~C60杂芳基组成的群组;
R8、R9各自表示一个或多个至饱和取代。
本发明意义上的芳基或芳香基含有6~60个碳原子,杂芳基或杂环芳基含有2~60个碳原子和至少一个杂原子,其条件是碳原子和杂原子的总和至少是5;所述杂原子优选选自N、O或S。此处的芳基或杂芳基涵盖单环基团和多环系统。多环可以具有两个碳为两个邻接环或称为“稠合的”共用的两个或更多个环,其中所述环中的至少一者是芳香族的,例如其它环可以是环烷基、环烯基、芳基、杂环和/或杂芳基。另外,多个芳基或杂芳基还可以由非芳族单元例如C、N、O或S原子连接,例如,和其中两个或更多个芳基被例如短的烷基连接的体系一样,诸如芴、9,9’-螺二芴、9,9-二芳基芴,三芳基胺、二芳基醚、二苯并呋喃或二苯并噻吩等。作为芳基和杂芳基的非限制性例子,特别是选自由取代或未取代的以下所述基团组成的群组:苯基、萘基、蒽基、苯并蒽基、菲基、芘基、基、苝基、荧蒽基、并四苯基、并五苯基、苯并芘基、联苯基、偶苯基、三联苯基、三聚苯基、四联苯基、芴基、螺二芴基、二氢菲基、三亚苯基、二氢芘基、四氢芘基、顺式或反式茚并芴基、顺式或反式茚并咔唑基、吲哚并咔唑基、苯并呋喃并咔唑基、苯并噻吩并咔唑基、苯并咔唑基、二苯并咔唑基、氮杂二苯并[g,id]萘并[2,1,8-cde]薁基、三聚茚基、异三聚茚基、螺三聚茚基、螺异三聚茚基、呋喃基、苯并呋喃基、异苯并呋喃基、二苯并呋喃基、噻吩基、苯并噻吩基、异苯并噻吩基、二苯并噻吩基、吡咯基、吲哚基、异吲哚基、咔唑基、吡啶基、喹啉基、异喹啉基、吖啶基、菲啶基、苯并[5,6]喹啉基、苯并[6,7]喹啉基、苯并[7,8]喹啉基、吩噻嗪基、吩噁嗪基、吡唑基、吲唑基、咪唑基、苯并咪唑基、萘并咪唑基、菲并咪唑基、吡啶并咪唑基、吡嗪并咪唑基、喹喔啉并咪唑基、噁唑基、苯并噁唑基、萘并噁唑基、蒽并噁唑基、菲并噁唑基、异噁唑基、1,2-噻唑基、1,3-噻唑基、苯并噻唑基、哒嗪基、六氮杂苯并菲基、苯并哒嗪基、嘧啶基、苯并嘧啶基、喹喔啉基、1,5-二氮杂蒽基、2,7-二氮杂芘基、2,3-二氮杂芘基、1,6-二氮杂芘基、1,8-二氮杂芘基、4,5-二氮杂芘基、4,5,9,10-四氮杂苝基、吡嗪基、吩嗪基、吩噁嗪基、吩噻嗪基、荧红环基、萘啶基、氮杂咔唑基、苯并咔啉基、咔啉基、菲咯啉基、1,2,3-三唑基、1,2,4-三唑基、苯并三唑基、1,2,3-噁二唑基、1,2,4-噁二唑基、1,2,5-噁二唑基、1,3,4-噁二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,2,5-噻二唑基、1,3,4-噻二唑基、1,3,5-三嗪基、1,2,4-三嗪基、1,2,3-三嗪基、四唑基、1,2,4,5-四嗪基、1,2,3,4-四嗪基、1,2,3,5-四嗪基、嘌呤基、蝶啶基、吲嗪基、喹唑啉基、苯并噻二唑基组成的群组或者衍生自这些体系的组合的基团。
本发明中使用的烷基是指碳原子数从1至40的直链或支链的饱和烃去除一个氢原子而得到的一价官能团。作为其非限制性例子1有甲基、乙基、丙基、异丁基、仲丁基、戊基、异戊基、己基等。杂烷基是指烷基上的氢原子或-CH2-被至少一个杂原子取代,所述杂原子选自卤素、腈基、N、O、S或硅,作为非限制性的例子,有二氟甲基、三氟甲基、三氟乙基、五氟乙基、腈基、乙腈基、甲氧基甲基、甲氧基乙基、三甲基硅基、三异丙基硅基等。
本发明中使用的烯基是指从具有一个以上碳碳双键的碳原子数从2至40的直链或支链的不饱和烃去除一个氢原子而得到的一价官能团。作为其非限制性例子,有乙烯基、烯丙基、异丙烯基、2-丁烯基等。
本发明中使用的炔基是指具有一个以上碳碳三键的碳原子数从2至40的直链或支链的不饱和烃去除一个氢原子而得到的一价官能团。作为其非限制性例子,有乙炔基、2-丙炔基等。
一般来说,根据本发明的环烷基、环烯基是指碳原子数从3至40的单环或多环非芳族烃去除一个氢原子而得到的一价官能团。作为其非限制性例子,有环丙基、环丁基、环戊基、环己基、降冰片基、金刚烷基、环丁烯基、环戊烯基、环己烯基、环庚基、环庚烯基,其中一个或多个-CH2-基团可被上述基团代替;此外,一个或多个氢原子还可被氘原子、卤素原子或腈基代替。
本发明中使用的杂环烷基是指原子核数从3至40的非芳香族烃去除一个氢原子而得到的一价官能团。此时,环中一个以上的碳、优选为1至3个碳被诸如N、O或S之类的杂原子取代。作为其非限制性例子,有四氢呋喃基基、四氢噻吩基、吗啉基、哌嗪基等。
本发明中使用的芳氧基或杂芳氧基是指RO-所表示的一价官能团,上述R是碳原子数从6至60的芳基或碳原数从2至60的杂芳基。作为这样的芳氧基或杂芳氧基的非限制性例子,有苯氧基、萘氧基、联苯氧基、2-吡啶氧基、3-吡啶氧基、4-吡啶氧基等。
本发明使用的芳基胺基,是指被碳原子数6至60的芳基取代的氨基,或被两个碳原子数6至60的芳基取代的仲胺基,作为芳基胺基的非限制性例子,有苯胺基、二苯胺基、1-萘胺基、2-萘胺基、N-苯基萘-1-胺基、咔唑基、吩噁嗪基等。
本发明中使用的“卤素”或“卤原子”是指选自氟、氯、溴或碘。
如本文所使用,“其组合”或“群组”表示适用清单的一或多个成员被组合以形成本领域普通技术人员能够从适用清单中设想的已知或化学稳定的布置。举例来说,烷基和氘可以组合形成部分或完全氘化的烷基;卤素和烷基可以组合形成卤代烷基取代基,例如三氟甲基等;并且卤素、烷基和芳基可以组合形成卤代芳烷基。
作为优选,所述R1、R2、R3、R4、R5、R6、R7、R8、R9各自独立地选自由以下基团组成的群组:氢、氘、腈基、甲基、乙基、异丙基、异丁基、叔丁基、取代或未取代的苯基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的四联苯基、取代或未取代的吡啶基、取代或未取代的嘧啶基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的三亚苯基、取代或未取代的蒽基、取代或未取代的苯并蒽基、取代或未取代的芘基、取代或未取代的基、取代或未取代的苝基、取代或未取代的荧蒽基、取代或未取代的咔唑基、取代或未取代的芴基、取代或未取代的吲哚基、取代或未取代的苯并呋喃基、取代或未取代的苯并噻吩基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基、取代或未取代的三嗪基组成的群组。
进一步地,所述R1、R2、R3、R4、R5、R6、R7、R8、R9各自独立地选自氢或氘。
作为优选,所述m为0、1或2。
作为优选,所述Ar1选自由取代或未取代的以下基团组成的群组:苯基、萘基、蒽基、苯并蒽基、菲基、芘基、基、苝基、荧蒽基、并四苯基、并五苯基、苯并芘基、联苯基、偶苯基、三联苯基、三聚苯基、四联苯基、芴基、螺二芴基、二氢菲基、三亚苯基、二氢芘基、四氢芘基、顺式或反式茚并芴基、顺式或反式茚并咔唑基、吲哚并咔唑基、苯并呋喃并咔唑基、苯并噻吩并咔唑基、苯并咔唑基、二苯并咔唑基、氮杂二苯并[g,id]萘并[2,1,8-cde]/>三聚茚基、异三聚茚基、螺三聚茚基、螺异三聚茚基、呋喃基、苯并呋喃基、异苯并呋喃基、二苯并呋喃基、噻吩基、苯并噻吩基、异苯并噻吩基、二苯并噻吩基、吡咯基、吲哚基、异吲哚基、咔唑基、吡啶基、喹啉基、异喹啉基、吖啶基、菲啶基、苯并[5,6]喹啉基、苯并[6,7]喹啉基、苯并[7,8]喹啉基、吩噻嗪基、吩噁嗪基、吡唑基、吲唑基、咪唑基、苯并咪唑基、萘并咪唑基、菲并咪唑基、吡啶并咪唑基、吡嗪并咪唑基、喹喔啉并咪唑基、噁唑基、苯并噁唑基、萘并噁唑基、蒽并噁唑基、菲并噁唑基、异噁唑基、1,2-噻唑基、1,3-噻唑基、苯并噻唑基、哒嗪基、六氮杂苯并菲基、苯并哒嗪基、嘧啶基、苯并嘧啶基、喹喔啉基、1,5-二氮杂蒽基、2,7-二氮杂芘基、2,3-二氮杂芘基、1,6-二氮杂芘基、1,8-二氮杂芘基、4,5-二氮杂芘基、4,5,9,10-四氮杂苝基、吡嗪基、吩嗪基、吩噁嗪基、吩噻嗪基、荧红环基、萘啶基、氮杂咔唑基、苯并咔啉基、咔啉基、菲咯啉基、1,2,3-三唑基、1,2,4-三唑基、苯并三唑基、1,2,3-噁二唑基、1,2,4-噁二唑基、1,2,5-噁二唑基、1,3,4-噁二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,2,5-噻二唑基、1,3,4-噻二唑基、1,3,5-三嗪基、1,2,4-三嗪基、1,2,3-三嗪基、四唑基、1,2,4,5-四嗪基、1,2,3,4-四嗪基、1,2,3,5-四嗪基、嘌呤基、蝶啶基、吲嗪基、喹唑啉基、苯并噻二唑基组成的群组或者衍生自这些体系的组合的基团。
进一步地,所述Ar1选自由以下II-1~II-17所示基团组成的群组:
其中,
Z1、Z2各自独立地选自由氢、氘、卤素、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1~C40烷基、C2~C40烯基、C2~C40炔基、C1~C40烷氧基、C3~C40环烷烃基、C3~C40环烯烃基、取代或未取代的C6~C60芳基、取代或未取代的C6~C60芳氧基、取代或未取代的C6~C60芳硫醚基、或者取代或未取代的C2~C60杂环芳基组成的群组;
x1表示1-4的整数;x2表示1-3的整数;x3表示1或2;x4表示1-6的整数;x5表示1-5的整数;
T1表示O、S、CR’R”或NAr’;
R’、R”各自独立地选自由氢、氘、C1~C40的烷基、C1~C40的杂烷基、取代或未取代的C6~C60芳基、取代或未取代的C6~C60芳胺基、或者取代或未取代的C5~C60杂环芳基组成的群组,R’和R”可任选地接合或稠合形成另外的一个或多个取代或未取代的环,在所形成的环中含有或不含有一个或多个杂原子N、P、B、O或S;优选地,R’、R”为甲基、苯基或芴基;
Ar’选自由C1~C40的烷基、C1~C40的杂烷基、C3~C40的环烷基、取代或未取代的C6~C60芳基、取代或未取代的C6-C60稠环芳基、取代或未取代的C6~C60芳胺基、或者取代或未取代的C5~C60杂环芳基组成的群组;优选地,Ar’为甲基、乙基、苯基、联苯基或萘基;
表示取代基与L1的连接键。
本发明中的亚芳基是指碳原子数从6至60的芳烃去除两个氢原子而得到的二价官能团。作为其非限制性例子,有亚苯基、亚联苯基、亚萘基、亚菲基、亚蒽基、亚芴基、亚螺二芴基等。
本发明中的亚杂芳基或杂亚芳基是指碳原子数从5至60的杂芳烃去除两个氢原子而得到的二价官能团。作为其非限制性例子,有亚吡啶基、亚喹啉基、亚异喹啉基、亚咔啉基、亚嘧啶基、亚三嗪基等。
根据前文所述的亚芳基、亚杂芳基作为二价官能团与Ar1的连接或与NAr2Ar3的连接,优选地,所述L1、L2各自独立地选自单键或由以下III-1~III-24所示基团组成的群组:
其中,T2选自O、S、Se、CR’R”、SiR’R”或NAr’;
z11、z12、z13、z14各自独立地选自由氢、氘、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C40的烷基、C2-C40的烯基、C2-C40的炔基、C1-C40的烷氧基、C3-C40的环烷烃基、C3-C40的环烯烃基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳氧基、取代或未取代的C6-C60芳硫醚基、或者取代或未取代的C5-C60杂芳基组成的群组;
y1表示1-4的整数;y2表示1-6的整数;y3表示1-3的整数;y4表示1-5的整数;y5表示1或2的整数;
R’、R”各自独立地选自由C1-C40的烷基、C1-C40的杂烷基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂芳基组成的群组,R’和R”可任选地接合或稠合形成另外的一个或多个取代或未取代的环,在所形成的环中含有或不含有一个或多个杂原子N、P、B、O或s;优选地,R’、R”为甲基、苯基或芴基;
Ar’选自由C1-C40的烷基、C1-C40的杂烷基、C3-C40的环烷基、取代或未取代的C6-C60芳基、取代或未取代的C10-C60稠环芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组;优选地,Ar’为甲基、乙基、苯基、联苯基或萘基;
其中,虚线代表基团的连接位点。
作为优选,所述L1、L2各自独立地选自单键或III-1~III-15、III-24所示基团组成的群组。
优选地,所述Z11、Z12、Z13、Z14各自独立地选自由氢、氘、氟、腈基组成的群组。
作为优选,所述T2选自O或S。
作为优选,所述咔唑衍生物选自以下CJH200~CJH370所示的结构中的一种或多种:
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*-和-*表示连接键。
本发明还提供以上所述的咔唑衍生物在有机电致发光元件中的应用。
本发明还提供一种有机电致发光元件,包括:第一电极、第二电极和位于所述第一电极和所述第二电极之间的至少一层有机层,所述有机层中至少一层包括以上所述的咔唑衍生物。
所述有机电致发光元件包含阴极、阳极和至少一个发光层。除了这些层之外,它还可以包含其它的层,例如在每种情况下,包含一个或多个空穴注入层、空穴传输层、空穴阻挡层、电子传输层、电子注入层、激子阻挡层、电子阻挡层和/或电荷产生层。具有例如激子阻挡功能的中间层同样可引入两个发光层之间。然而,应当指出,这些层中的每个并非必须都存在。此处所述有机电致发光装置可包含一个发光层,或者它可包含多个发光层。即,将能够发光的多种发光化合物用于所述发光层中。特别优选具有三个发光层的体系,其中所述三个层可显示蓝色、绿色和红色发光。如果存在多于一个的发光层,则根据本发明,这些层中的至少一个层包含本发明的咔唑衍生物。
在根据本发明的有机电致发光元件的其它层中,特别是在空穴传输层和薄膜封装层中,所有材料可以按照根据现有技术通常所使用的方式来使用。本领域普通技术人员因此将能够在不付出创造性劳动的情况下与根据本发明的发光层组合使用关于有机电致发光元件所知的所有材料。
此外优选如下的有机电致发光元件,借助于升华方法施加一个或多个层,其中在真空升华装置中在低于10-5Pa、优选低于10-6Pa的初压下通过气相沉积来施加所述材料。然而,所述初压还可能甚至更低,例如低于10-7Pa。
同样优选如下的有机电致发光元件,借助于有机气相沉积方法或借助于载气升华来施加一个或多个层,其中,在10-5Pa至1Pa之间的压力下施加所述材料。该方法的特别的例子是有机蒸汽喷印方法,其中所述材料通过喷嘴直接施加,并且因此是结构化的。
此外优选如下的有机电致发光元件,从溶液中,例如通过旋涂,或借助于任何所希望的印刷方法例如丝网印刷、柔性版印刷、平版印刷、光引发热成像、热转印、喷墨印刷或喷嘴印刷,来产生一个或多个层。可溶性化合物,例如通过适当的取代式(I)所示的化合物获得可溶性化合物。这些方法也特别适于低聚物、树枝状大分子和聚合物。此外可行的是混合方法,其中例如从溶液中施加一个或多个层并且通过气相沉积施加一个或多个另外的层。从液相处理本发明的化合物,例如通过旋涂或通过印刷方法进行处理,需要处理本发明的化合物的制剂。这些制剂可以例如是溶液、分散体或乳液。出于这个目的,可优选使用两种或更多种溶剂的混合物。合适并且优选的溶剂例如是甲苯、苯甲醚、邻二甲苯、间二甲苯或对二甲苯、苯甲酸甲酯、均三甲苯、萘满、邻二甲氧基苯、四氢呋喃、甲基四氢呋喃、四氢吡喃、氯苯、二噁烷、苯氧基甲苯、特别是3-苯氧基甲苯、(-)-葑酮、1,2,3,5-四甲基苯、1,2,4,5-四甲基苯、1-甲基萘、2-甲基苯并噻唑、2-苯氧基乙醇、2-吡咯烷酮、3-甲基苯甲醚、4-甲基苯甲醚、3,4-二甲基苯甲醚、3,5-二甲基苯甲醚、苯乙酮、α-萜品醇、苯并噻唑、苯甲酸丁酯、异丙苯、环己醇、环己酮、环己基苯、十氢化萘、十二烷基苯、苯甲酸乙酯、茚满、苯甲酸甲酯、1-甲基吡咯烷酮、对甲基异丙基苯、苯乙醚、1,4-二异丙基苯、二苄醚、二乙二醇丁基甲基醚、三乙二醇丁基甲基醚、二乙二醇二丁基醚、三乙二醇二甲基醚、二乙二醇单丁基醚、三丙二醇二甲基醚、四乙二醇二甲基醚、2-异丙基萘、戊苯、己苯、庚苯、辛苯、1,1-双(3,4-二甲基苯基)乙烷,或这些溶剂的混合物。
作为优选,所述有机电致发光元件的有机层选自电子输送层、空穴阻挡层、电子阻挡层、空穴传输层、空穴注入层、发光层和电荷产生层中的一种或几种。
进一步的,所述电子输送层、发光层、封盖层或电荷产生层包含本发明的咔唑衍生物。
作为优选,所述咔唑衍生物在有机电致发光元件中用作发光层材料、空穴传输层材料或封装层材料。
更进一步地,所述发光层包含本发明的咔唑衍生物。
进一步的,所述发光层包括掺杂物和发光主体,所述掺杂物包括由蒽、萘、蒽、芘、苝、菲、荧蒽、苯并蒽、芴、螺芴和并五苯及其衍生物或含有硼原子的化合物组成的群组,此外,还能够使用各种金属络合物、双苯乙烯基苯衍生物、噁唑衍生物、聚对亚苯基亚乙烯基衍生物、具有吲哚环作为稠环的部分结构的杂环化合物、具有咔唑环作为稠环的部分结构的杂环化合物、咔唑衍生物、噻唑衍生物、苯并咪唑衍生物、聚二烷基芴衍生物等。另外,作为掺杂剂材料,除此以外,还能够使用:在分子中具有芘骨架的芘衍生物、具有吲哚环作为稠环的部分结构的杂环化合物、具有咔唑环作为稠环的部分结构的杂环化合物、咔唑衍生物、噻唑衍生物、苯并咪唑衍生物、聚二烷基芴衍生物、喹吖啶酮、香豆素、红荧烯、苝及它们的衍生物、苯并吡喃衍生物、茚并菲衍生物、罗丹明衍生物、氨基苯乙烯基衍生物等。它们可以单独成膜,也可以作为与其他材料一起混合而成膜的单层使用,也可以作为单独成膜的层之间、混合而成膜的层之间、或者单独成膜的层与混合而成膜的层的层叠结构。
另外,也可以使用磷光发光体作为掺杂物。作为磷光发光体,能够使用铱、铂等金属络合物的磷光发光体。可使用Ir(ppy)3等绿色磷光发光体、Firpic、Fir6等蓝色磷光发光体、Btp2Ir(acac)等红色磷光发光体等,作为此时的主体材料,优选使用本发明的咔唑衍生物。此外,作为空穴注入、传输性的主体材料(P型材料),能够使用4,4’-二(N-咔唑基)联苯(cBP)、4,4′,4′-三(咔唑-9-基)三苯胺(TCTA)、9,9′-(1,3-苯基)二-9H-咔唑(mCP)等咔唑衍生物等。作为电子传输性的主体材料(n型材料),能够使用对-双(三苯基甲硅烷基)苯(UGH2)、2,2’,2”-(1,3,5-亚苯基)-三(1-苯基-1H-苯并咪唑)(TPBI)等,能够制作高性能的发光元件。
就磷光性的发光材料向主体材料的掺杂而言,为了避免浓度淬灭,优选在相对于发光层重量为1~10%的范围内通过共蒸镀进行掺杂。
另外,作为发光掺杂材料,也可以使用2-联苯基-4,6-双(12-苯基吲哚并[2,3-a]咔唑-11-基)-1,3,5-三嗪(PIC-TRz)、9,9″-(6-苯基-1,3,5-三嗪-2,4-二基)双((9H-3,9′-联咔唑))(CC2TA)、苯并恶嗪-2,4,6-三苯基-1,3,5-三嗪(PXZ-TRZ)、2,4,5,6-四(9-咔唑基)-间苯二腈(4CzIPN)等发射延迟荧光的材料。
进一步的,所述发光层主体材料包含本发明的咔唑衍生物。
进一步的,所述的掺杂物与发光主体的质量比为1∶99~50∶50。
本发明的有机电致发光元件既可以是顶发射光元件,又可以是底发射光元件。本发明的有机电致发光元件的结构和制备方法没有限定。采用本发明的化合物制得的有机电致发光元件可降低启动电压、提高发光效率和亮度。
本发明同时提供一种显示装置,包括以上所述的有机电致发光元件。
本发明同时提供一种照明装置,包括以上所述的有机电致发光元件。
一种由所述的有机电致发光装置制成的消费型产品,所述消费型产品包括本发明提供的有机电致发光装置。
本发明中所述的消费型产品可以是以下产品中的一种:平板显示器、计算机监视器、医疗监视器、电视机、告示牌、用于内部或外部照明和/或发信号的灯、平视显示器、全透明或部分透明的显示器、柔性显示器、激光打印机、电话、蜂窝电话、平板电脑、平板手机、个人数字助理(PDA)、可佩戴装置、膝上型计算机、数码相机、摄像机、取景器、对角线小于2英寸的微型显示器、3-D显示器、虚拟现实或增强现实显示器、交通工具、包含多个平铺在一起的显示器的视频墙、剧院或体育馆屏幕、光疗装置和指示牌。
与现有技术相比,本发明的有益效果为:
本发明所述的咔唑衍生物具有萘并吲哚联咔唑的新颖结构,具有输送电子和空穴的双极性,适宜作为有机电致发光元件用材料使用;含有所述咔唑衍生物的有机电致发光元件用材料,具有启动电压低,发光效率和亮度高的特点。另外,本发明的咔唑衍生物具有良好的热稳定性和成膜性能,应用在有机电致发光元件用材料、有机电致发光元件、显示装置、照明装置中,能够延长使用寿命,从而能够降低功耗和制造成本。
附图说明
为了更清楚地说明本发明实施例或现有技术中的技术方案,下面将对实施例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,下面描述中的附图仅仅是本发明的一些实施例,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展示有机发光装置100示意图。图示不一定按比例绘制。装置100可包含衬底101、阳极102、空穴注入层103、空穴传输层104、电子阻挡层105、发光层106、空穴阻挡层107、电子传输层108、电子注入层109、阴极110以及封盖层(CPL)111。装置100可通过依序沉积所描述的层来制造。
图2展示两个发光层的有机发光装置200示意图。所述装置包含衬底201、阳极202、空穴注入层203、空穴传输层204、第一发光层205、电子传输层206、电荷产生层207、空穴注入层208、空穴传输层209、第二发光层210、电子传输层211、电子注入层212以及阴极213。可通过依序沉积所描述的层来制备装置200。因为最常见的OLED装置具有一个发光层,而装置200具有第一发光层和第二发光层,第一发光层和第二发光层的发光峰形可以是重叠的或交叉重叠的或非重叠的。在装置200的对应层中,可使用与关于装置100所描述的材料类似的材料。图2提供如何从装置100的结构增加一些层的一个实例。
具体实施方式
为使本发明的目的、技术方案和优点更加清楚,下面将对本发明的技术方案进行详细的描述。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的前提下所得到的所有其它实施方式,都属于本发明所保护的范围。
以下实施例中OLED材料及元件进行性能测试的测试仪器及方法如下:
OLED元件性能检测条件:
亮度和色度坐标:使用光谱扫描仪PhotoResearch PR-715测试;
电流密度和起亮电压:使用数字源表Keithley 2420测试;
功率效率:使用NEWPORT 1931-C测试;
寿命测试:使用LTS-1004AC寿命测试装置。
实施例1
化合物CJH202的制备方法,包括如下步骤:
第一步:化合物Int-1的制备
在氮气氛围下,20.0mmol的1-嘧啶基吲哚、40.0mmol的5-氯苯并环丁烯酮、0.6mmol的Ru3(CO)12、1.2mmol的二苯基氧磷和4.0mmol的2M无水氯化锌THF溶液以及60mL的1,4-二氧六环,升温至140℃搅拌反应36小时,降到室温,用短的硅胶柱过滤,二氯甲烷洗脱,滤液减压浓缩干,用硅胶柱分离纯化,得到化合物Int-1,黄色固体,收率:65%。
第二步:化合物Int-2的制备
在氮气氛围下,20.0mmol的中间体Int-1溶于60mL的二氯甲烷中,加入50.0mmol的吡啶,降温至0℃,滴加入30.0mmol的三氟甲烷磺酸酐,升至室温搅拌反应12小时,加入100mL的冰水,分出有机相,水相用二氯甲烷萃取,收集有机相用2M稀盐酸洗、水洗,有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到中间体Int-2,收率:92%。
第三步:化合物Int-3的制备
在氮气氛围下,20.0mmol的中间体Int-2、20.0mmol的咔唑溶于80mL的二甲苯中,再加入60.0mmol的叔丁醇钠、2.0mmol的碘化亚铜、0.2mmol的Pd2(dba)3和0.5mmol的10%三叔丁基磷甲苯溶液,升温至120℃搅拌反应15小时,降至室温,加入50mL的水,分出有机相,水相用二氯甲烷萃取,收集有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到中间体Int-3,收率:83%。
第四步:化合物Int-4的制备
在氮气氛围下,20.0mmol的中间体Int-3、80.0mmol的乙醇钠溶于50mL的DMSO中,升温至100℃搅拌反应24小时,降至室温,加入150mL的2M稀盐酸水溶液,用二氯甲烷萃取,收集有机相用水洗,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到中间体Int-4,收率:65%。
第五步:化合物CJH202的制备
在氮气氛围下,30.0mmol的氢氧化钠溶于50mL的DMSO中,于室温搅拌反应1小时,加入20.0mmol的中间体Int-4(反应物1),搅拌反应1小时,再加入22.0mmol的2-间联苯基-4-氯-6-苯基-1,3,5-三嗪(反应物2),升温至45℃搅拌反应15小时,降至室温,加入150mL的冰水,过滤,滤饼用水洗,用硅胶柱分离纯化,再用甲苯/THF重结晶,得到化合物CJH202,收率:84%,HRMS:m/z688.2509[M+H]+。1HNMR(δ、CDCl3):9.14(1H,s);8.78(1H,s);8.61~8.56(3H,m);8.43~8.30(6H,m);8.20~8.15(2H,m);7.87~7.80(2H,m);7.78~7.70(3H,m);7.60~7.51(2H,m);7.45~7.29(9H,m)。
实施例2~实施例86
参照上述类似的合成方法,制备如表1所示化合物:
表1
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实施例87
化合物CJH273的制备:
15.0mmol化合物Int-4溶解于80mL干燥的甲苯中,在氮气保护下,加入16.5mmol的2-(2-溴苯基)-4,6-二苯基-1,3,5-三嗪和22.5mmol的叔丁醇钠,再加入0.1mmol的Pd2(dba)3CHCl3和0.02mL的10%三叔丁磷甲苯溶液,升温至100℃,搅拌反应15小时,冷却到室温,加入50mL水稀释,用二氯甲烷萃取,收集有机相,干燥,过滤,滤液减压浓缩干燥,用硅胶柱分离纯化,得到化合物CJH273,黄色固体,收率86%,MS(MALDI-TOF):m/z 688.2439[M+H]+;1HNMR(δ、CDCl3):8.53(1H,s);8.36~8.32(4H,m);8.17~8.12(2H,m);8.05~8.01(1H,t);7.93~7.87(3H,m);7.83~7.78(2H,m);7.70~7.64(2H,m);7.59~7.55(1H,m);7.53~7.44(7H,m);7.42~7.37(3H,m);7.35~7.31(1H,m);7.19~7.14(2H,m)。
实施例88~实施例173
参照上述实施例类似的合成方法,制备如表2所示的化合物:
表2
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上述实施例中,*-X-*选自*-O-*、*-S-*或下述结构中的一种:
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*-和-*表示连接键。
有机电致发光元件(如图1和图2所示)的制备
应用例1
一种OLED元件100,如图1所示,本实施例的OLED元件为顶发射光元件,包括基板101、设于基板101上的阳极102、设于阳极102上的空穴注入层103、设于空穴注入层103上的空穴传输层104、设于空穴传输层104上的电子阻挡层105、设于电子阻挡层105上的发光层106、设于发光层106上的空穴阻挡层107、设于空穴阻挡层107上的电子传输层108、设于电子传输层108上的电子注入层109以及设于电子注入层109上的阴极110和阴极之上的封盖层111,省略空穴阻挡层107的OLED元件的制备方法包括如下步骤:
1)将涂布了ITO导电层的玻璃基片在清洗剂中超声处理30分钟,在去离子水中冲洗,在丙酮/乙醇混合溶剂中超声30分钟,在洁净的环境下烘烤至完全干燥,用紫外光清洗机照射10分钟,并用低能阳离子束轰击表面;
2)把上述处理好的ITO玻璃基片置于真空腔内,抽真空至小于1×10-5Pa,在上述ITO上蒸镀金属银作为阳极,蒸镀膜厚为继续分别蒸镀化合物HI01和F4TCNQ作为空穴注入层,其中,F4TCNQ为H101质量的3%,蒸镀膜厚为/>
3)在上述空穴注入层上继续蒸镀化合物HTM为空穴传输层,蒸镀膜厚为
4)在上述空穴传输层上继续蒸镀化合物HT022作为电子阻挡层,蒸镀膜厚为
5)在电子阻挡层上继续蒸镀本发明的式(I)所示化合物作为主体材料和RD026为掺杂材料,RD026为式(I)所示化合物质量的5%,作为元件的发光层,蒸镀所得有机发光层的膜厚为
6)在发光层上继续蒸镀一层LiQ和化合物ET033作为元件的电子传输层,其中,化合物ET033为LiQ质量的50%,蒸镀膜厚为
7)在电子传输层之上继续蒸镀一层LiF为电子注入层,蒸镀膜厚为
8)在电子注入层之上蒸镀金属镁和银作为元件的透明阴极,镁和银的质量比为1∶10,蒸镀膜厚为
9)在透明阴极之上再蒸镀一层CPD作为元件的CPL层,蒸镀膜厚为得到本发明提供的OLED元件。
上述应用例1中使用的化合物结构如下:
应用例2
一种有机电致发光元件200,其结构如图2所示,其包含衬底201、阳极层202、空穴注入层203、空穴传输层204、第一发光层205、电子传输层206、电荷产生层207、空穴注入层208、空穴传输层209、第二发光层210、电子传输层211、电子注入层212以及阴极层213,参照应用例1类似的制备方法制备电致发光元件200。
对比例1
按照与应用例1相同的步骤,仅将步骤5)中的本发明的式(I)化合物式替换为H01,得到对比元件1;
应用例3~应用例173
将上述实施例制备的本发明的咔唑衍生物进行真空升华提纯至99.90%以上,参照应用例1制备有机电致发光元件,并对上述过程制备的有机电致发光元件进行如下性能测试:
使用数字源表及亮度计测定上述应用例和对比例1中制备得到的有机电致发光元件的驱动电压和电流效率以及元件的寿命。具体而言,以每秒0.1V的速率提升电压,测定当有机电致发光元件的亮度达到1000cd/m2时的电压即驱动电压,同时测出此时的电流密度;亮度与电流密度的比值即为电流效率;LT95%寿命测试如下:使用亮度计在1000cd/m2亮度下,保持恒定的电流,测量有机电致发光元件的亮度衰减为950cd/m2的时间,单位为小时。表3中列出的数据是相较于对比元件1(括号内为测试数据)的相对数据。
表3
/>
/>
/>
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上述表中,Me为甲基,Ph为苯基,PhPh为联苯基。
由表3可知,本发明的咔唑衍生物制备的元件在相同的亮度下,驱动电压相较H01更低,电流效率提高明显,最高达到对比元件的1.26倍之多,而且元件的LT95%寿命有较大的改善,表明本发明的咔唑衍生物是性能优异的发光层材料。
对比例1中的化合物H01与本发明的化合物相比,区别在于,受体基团和供体基团的共轭平面位置不同,造成对比元件1效率降低的原因可能是受体基团和供体基团连接的氮原子与作为供体基团的咔唑氮原子距离较近,分子的HOMO和LUMO虽然实现了分离,但是HOMO和LUMO出现重叠,因此造成激子的内部淬灭和内转换,能量的损失使效率降低。而本发明的咔唑衍生物通过调整苯并吲哚的位置,实现了HOMO和LUMO的完全隔离,避免激子的传递过程中淬灭和损失,因此,其在分子成膜及激子传输性能上更优异,元件内激子的传送更加平衡,因此元件性能得到显著提高。
虽然,上文中已经用一般性说明及具体实施方案对本发明作了详尽的描述,但在本发明基础上,可以对之作一些修改或改进,这对本领域技术人员而言是显而易见的。因此,在不偏离本发明精神的基础上所做的这些修改或改进,均属于本发明要求保护的范围。
Claims (10)
1.一种咔唑衍生物,其特征在于,其结构如式(I)所示:
其中,
R1、R2、R3、R4、R5、R6、R7、R8、R9各自独立地选自由氢、氘、腈基、卤原子、取代或未取代的C1~C40直链烷基、取代或未取代的C1~C40直链杂烷基、取代或未取代的C3~C40支链或环状的烷基、取代或未取代的C3~C40支链或环状的杂烷基、取代或未取代的C2~C40烯基或炔基、取代或未取代的C6~C60芳基、取代或未取代的C6~C60芳基胺基、取代或未取代的C2~C60杂芳基、或*-L2NAr2Ar3组成的群组,R1~R9中的两个或更多个相邻的取代基团可以任意地接合或稠合形成取代或未取代的环;
L1、L2各自独立地选自由单键、取代或未取代的C6~C60亚芳基、取代或未取代的C5~C60亚杂芳基组成的群组;
m表示0~5的整数;
Ar1、Ar2、Ar3各自独立地选自由取代或未取代的C6~C60芳基、取代或未取代的C6~C60芳基胺基、取代或未取代的C2~C60杂芳基组成的群组;
R8、R9各自表示一个或多个至饱和取代。
2.根据权利要求1所述的咔唑衍生物,其特征在于,所述R1、R2、R3、R4、R5、R6、R7、R8、R9各自独立地选自由以下基团组成的群组:氢、氘、腈基、甲基、乙基、异丙基、异丁基、叔丁基、取代或未取代的苯基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的四联苯基、取代或未取代的吡啶基、取代或未取代的嘧啶基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的三亚苯基、取代或未取代的蒽基、取代或未取代的苯并蒽基、取代或未取代的芘基、取代或未取代的基、取代或未取代的苝基、取代或未取代的荧蒽基、取代或未取代的咔唑基、取代或未取代的芴基、取代或未取代的吲哚基、取代或未取代的苯并呋喃基、取代或未取代的苯并噻吩基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基、取代或未取代的三嗪基组成的群组;
m为0、1或2;
Ar1选自由取代或未取代的以下基团组成的群组:苯基、萘基、蒽基、苯并蒽基、菲基、芘基、基、苝基、荧蒽基、并四苯基、并五苯基、苯并芘基、联苯基、偶苯基、三联苯基、三聚苯基、四联苯基、芴基、螺二芴基、二氢菲基、三亚苯基、二氢芘基、四氢芘基、顺式或反式茚并芴基、顺式或反式茚并咔唑基、吲哚并咔唑基、苯并呋喃并咔唑基、苯并噻吩并咔唑基、苯并咔唑基、二苯并咔唑基、氮杂二苯并[g,id]萘并[2,1,8-cde]薁、三聚茚基、异三聚茚基、螺三聚茚基、螺异三聚茚基、呋喃基、苯并呋喃基、异苯并呋喃基、二苯并呋喃基、噻吩基、苯并噻吩基、异苯并噻吩基、二苯并噻吩基、吡咯基、吲哚基、异吲哚基、咔唑基、吡啶基、喹啉基、异喹啉基、吖啶基、菲啶基、苯并[5,6]喹啉基、苯并[6,7]喹啉基、苯并[7,8]喹啉基、吩噻嗪基、吩噁嗪基、吡唑基、吲唑基、咪唑基、苯并咪唑基、萘并咪唑基、菲并咪唑基、吡啶并咪唑基、吡嗪并咪唑基、喹喔啉并咪唑基、噁唑基、苯并噁唑基、萘并噁唑基、蒽并噁唑基、菲并噁唑基、异噁唑基、1,2-噻唑基、1,3-噻唑基、苯并噻唑基、哒嗪基、六氮杂苯并菲基、苯并哒嗪基、嘧啶基、苯并嘧啶基、喹喔啉基、1,5-二氮杂蒽基、2,7-二氮杂芘基、2,3-二氮杂芘基、1,6-二氮杂芘基、1,8-二氮杂芘基、4,5-二氮杂芘基、4,5,9,10-四氮杂苝基、吡嗪基、吩嗪基、吩噁嗪基、吩噻嗪基、荧红环基、萘啶基、氮杂咔唑基、苯并咔啉基、咔啉基、菲咯啉基、1,2,3-三唑基、1,2,4-三唑基、苯并三唑基、1,2,3-噁二唑基、1,2,4-噁二唑基、1,2,5-噁二唑基、1,3,4-噁二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,2,5-噻二唑基、1,3,4-噻二唑基、1,3,5-三嗪基、1,2,4-三嗪基、1,2,3-三嗪基、四唑基、1,2,4,5-四嗪基、1,2,3,4-四嗪基、1,2,3,5-四嗪基、嘌呤基、蝶啶基、吲嗪基、喹唑啉基、苯并噻二唑基组成的群组或者衍生自这些体系的组合的基团。
3.根据权利要求1所述的咔唑衍生物,其特征在于,所述Ar1选自由以下II-1~II-17所示基团组成的群组:
其中,
Z1、Z2各自独立地选自由氢、氘、卤素、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1~C40烷基、C2~C40烯基、C2~C40炔基、C1~C40烷氧基、C3~C40环烷烃基、C3~C40环烯烃基、取代或未取代的C6~C60芳基、取代或未取代的C6~C60芳氧基、取代或未取代的C6~C60芳硫醚基、或者取代或未取代的C2~C60杂环芳基组成的群组;
x1表示1-4的整数;x2表示1-3的整数;x3表示1或2;x4表示1-6的整数;x5表示1-5的整数;
T1表示O、S、CR’R”或NAr’;
R’、R”各自独立地选自由氢、氘、C1~C40的烷基、C1~C40的杂烷基、取代或未取代的C6~C60芳基、取代或未取代的C6~C60芳胺基、或者取代或未取代的C2~C60杂环芳基组成的群组,R’和R”可任选地接合或稠合形成另外的一个或多个取代或未取代的环,在所形成的环中含有或不含有一个或多个杂原子N、P、B、O或S;优选地,R’、R”为甲基、苯基或芴基;
Ar’选自由C1~C40的烷基、C1~C40的杂烷基、C3~C40的环烷基、取代或未取代的C6~C60芳基、取代或未取代的C6-C60稠环芳基、取代或未取代的C6~C60芳胺基、或者取代或未取代的C2~C60杂环芳基组成的群组;优选地,Ar’为甲基、乙基、苯基、联苯基或萘基;
表示取代基与L1的连接键。
4.根据权利要求1-3任一项所述的咔唑衍生物,其特征在于,所述R1、R2、R3、R4、R5、R6、R7、R8、R9各自独立地选自氢或氘;
所述L1、L2各自独立地选自单键或由以下III-1~III-24所示基团组成的群组:
其中,T2选自O、S、Se、CR’R”、SiR’R”或NAr’;
Z11、Z12、Z13、Z14各自独立地选自由氢、氘、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C40的烷基、C2-C40的烯基、C2-C40的炔基、C1-C40的烷氧基、C3-C40的环烷烃基、C3-C40的环烯烃基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳氧基、取代或未取代的C6-C60芳硫醚基、或者取代或未取代的C2-C60杂芳基组成的群组;
y1表示1-4的整数;y2表示1-6的整数;y3表示1-3的整数;y4表示1-5的整数;y5表示1或2;
R’、R”各自独立地选自由C1-C40的烷基、C1-C40的杂烷基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂芳基组成的群组,R’和R”可任选地接合或稠合形成另外的一个或多个取代或未取代的环,在所形成的环中含有或不含有一个或多个杂原子N、P、B、O或S;优选地,R’、R”为甲基、苯基或芴基;
Ar’选自由C1-C40的烷基、C1-C40的杂烷基、C3-C40的环烷基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60稠环芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组;优选地,Ar’为甲基、乙基、苯基、联苯基或萘基;
其中,虚线代表基团的连接位点。
5.根据权利要求1-4任一项所述的咔唑衍生物,其特征在于,所述咔唑衍生物选自以下CJH200~CJH370所示的结构中的一种或多种:
/>
其中,*-X-*选自*-O-*、*-S-*或下述结构中的一种:
*-和-*表示连接键。
6.权利要求1-5任一项所述的咔唑衍生物在有机电致发光元件中的应用。
7.根据权利要求6所述的应用,其特征在于,所述咔唑衍生物在有机电致发光元件中用作发光层材料、空穴传输层材料、空穴阻挡层材料或封装层材料。
8.一种有机电致发光元件,其特征在于,包括:第一电极、第二电极和位于所述第一电极和所述第二电极之间的至少一层有机层,所述有机层中至少一层包括权利要求1-5任一项所述的咔唑衍生物。
9.一种显示装置,其特征在于,包括权利要求8所述的有机电致发光元件。
10.一种照明装置,其特征在于,包括权利要求8所述的有机电致发光元件。
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