CN113292497B - 一种五元杂环衍生物及其有机电致发光器件 - Google Patents
一种五元杂环衍生物及其有机电致发光器件 Download PDFInfo
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- CN113292497B CN113292497B CN202110181008.2A CN202110181008A CN113292497B CN 113292497 B CN113292497 B CN 113292497B CN 202110181008 A CN202110181008 A CN 202110181008A CN 113292497 B CN113292497 B CN 113292497B
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 238000005406 washing Methods 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
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- Electroluminescent Light Sources (AREA)
Abstract
本发明提供了一种五元杂环衍生物及其有机电致发光器件，涉及有机光电材料技术领域。本发明的五元杂环衍生物通过将五元含氮杂环与刚性较大基团组合形成，特定的结构使得所述五元杂环衍生物具有良好的电子传输性能，具有高的玻璃化温度及热稳定性，分子的刚性以及不对称性增强，避免了分子间的聚集作用，具有分子间不易结晶、不易聚集、成膜性良好的特点。其可以应用在有机电致发光器件中，作为电子传输/空穴阻挡材料，可以解决现有材料中电子传输和/或空穴阻挡材料存在电子迁移率低、热稳定性差、易聚集结晶等问题，使用本发明衍生物制作的有机电致发光器件具有光电性能良好、驱动电压低、发光效率高、寿命长等特点。
Description
技术领域
本发明涉及有机光电材料技术领域，尤其涉及一种五元杂环衍生物及其有机电致发光器件。
背景技术
有机电致发光(OLED)器件技术既可以用来制造新型显示产品，也可以用于制作新型照明产品，有望替代现有的液晶显示和荧光灯照明，应用前景十分广泛。有机电致发光器件犹如三明治的结构，包括电极材料膜层，以及夹在不同电极膜层之间的有机功能材料，各种不同功能材料根据用途相互叠加在一起共同组成有机电致发光器件。作为电流器件，当对有机电致发光器件的两端电极施加电压，并通过电场作用有机层功能材料膜层中正负电荷，正负电荷进一步在发光层中复合，即产生有机电致发光。
应用于有机电致发光器件的有机功能材料从用途上大致可划分为两大类，即电荷注入/传输材料和发光材料，电荷注入/传输材料又可以分为电子注入/传输材料、电子阻挡材料、空穴注入/传输材料和空穴阻挡材料，而发光材料包括主体材料和掺杂材料。为了制作高性能的有机电致发光器件，各种有机功能材料必须具备良好的光电特性，譬如，作为电荷传输材料，要求具有良好的载流子迁移率，高玻璃化转化温度等，作为发光层的主体材料必须具备良好的双极性，适当的HOMO/LUMO能级等。对于有机电致发光器件提高性能的研究主要包括：降低器件的驱动电压，提高器件的发光效率，提高器件的使用寿命等。
为了使有机电致发光器件的发光效率最大化，良好的电子和空穴传输平衡是非常重要的，但现有材料中电子传输/空穴阻挡材料存在电子迁移率低、热稳定性差、易聚集结晶等问题，因此设计良好的电子传输/空穴阻挡材料意义重大。
发明内容
针对现有技术存在的上述问题，本发明提供了一种五元杂环衍生物及其有机电致发光器件。使用本发明衍生物制作出的有机电致发光器件光电性能良好，具有驱动电压低、发光效率高、寿命长等特点。
本发明提供了一种五元杂环衍生物，所述五元杂环衍生物如下式Ⅰ所示：
A选自下式Ⅱ表示的基团，Q选自下式Ⅲ表示的基团：
其中，X选自O、S、N-R20中的任意一种；M选自C、Si、Ge中的任意一种；
L选自单键、取代或未取代的C6-C30的亚芳基、取代或未取代的C2-C30的亚杂芳基中的任意一种；
Y1、Y2独立地选自O、S、C-R21R22、N-R23中的任意一种，n、m独立地选自0或1，当n或m为0时，为单键连接；
R1-R23独立地选自氢、氘、氚、氟、氯、溴、碘、氰基、硝基、羟基、羰基、酮基、酯基、酰胺基、取代或未取代的C1-C50的烷基、取代或未取代的C3-C50的环烷基、取代或未取代的C2-C50的烯基、取代或未取代的C2-C50的炔基、取代或未取代的C1-C50的烷氧基、取代或未取代的C3-C50的环烷氧基、取代或未取代的C6-C50的芳氧基、取代或未取代的C1-C50的烷基硫基、取代或未取代的C6-C50的芳基硫基、取代或未取代的C1-C50的烷基磺酰基、取代或未取代的C6-C50的芳基磺酰基、取代或未取代的C1-C50的甲硅烷基、取代或未取代的C1-C50的硼基、取代或未取代的C6-C50的芳基膦基、取代或未取代的C1-C50的氧化膦基、取代或未取代的C6-C50的芳基、取代或未取代的C2-C50的杂芳基中的任意一种，且任选地R4-R19中相邻基团可以结合成环；条件是，R1-R3、R20中的一个为单键并与L键连，R4-R19中的一个为单键并与L键连。
本发明还提供了一种有机电致发光器件，包括阳极、阴极以及有机功能层，所述有机功能层包括电子传输层和/或空穴阻挡层，所述电子传输层和/或空穴阻挡层含有至少一种本发明所述的五元杂环衍生物。
本发明还提供了一种照明或显示元件，所述照明或显示元件包括本发明所述的有机电致发光器件。
本发明有益效果：
本发明所述五元杂环衍生物通过将五元含氮杂环与刚性较大基团组合形成，特定的结构使得所述五元杂环衍生物具有良好的电子传输性能，具有高的玻璃化温度及热稳定性，分子的刚性以及不对称性增强，避免了分子间的聚集作用，具有分子间不易结晶、不易聚集、成膜性良好的特点。因此，本发明衍生物应用于有机电致发光器件时，能够延长器件使用寿命和提高发光效率；同时，能够非常明显的改善器件的驱动电压，在有机电致发光器件中具有良好的应用效果，有良好的产业化前景。
附图说明
图1为本发明的化合物2的1H NMR图；图2为本发明的化合物18的1H NMR图；
图3为本发明的化合物93的1H NMR图；图4为本发明的化合物112的1H NMR图；
图5为本发明的化合物351的1H NMR图。
具体实施方式：
下面将结合本发明实施例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，都属于本发明的保护范围。
在本发明中，所述烷基可以是直链烷基或支链烷基，优选具有1至50个碳原子，更优选1至30个碳原子，特别优选1至15个碳原子，最优选1至6个碳原子。所述烷基可以是取代或未取代的。具体实例包括甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、1-甲基-丁基、1-乙基-丁基、正戊基、异戊基、新戊基、叔戊基、正己基、1-甲基戊基、2-甲基戊基、4-甲基-2-戊基、2-乙基丁基、1-甲基己基、正辛基、2-乙基己基、1-乙基-丙基、2-甲基戊基、4-甲基己基、5-甲基己基等，但不限于此。
在本发明中，所述环烷基优选具有3至50个碳原子，更优选3至30个碳原子，特别优选3至15个碳原子，最优选3至6个碳原子。所述环烷基可以是取代或未取代的。具体实例包括环丙基、环丁基、环戊基、2,3-二甲基环戊基、环己基、4-甲基环己基、2,3-二甲基环己基、3,4,5-三甲基环己基、4-叔丁基环己基、环庚基、莰烷基、降冰片烷基、金刚烷基等，但不限于此。
在本发明中，所述烷氧基可以是直链或支链的，上述关于烷基的描述可以应用于烷氧基的烷基部分。所述烷氧基可以是取代或未取代的。具体实例包括甲氧基、乙氧基、正丙氧基、异丙氧基、异丙基氧基、正丁氧基、异丁氧基、叔丁氧基、仲丁氧基、正戊氧基、新戊氧基、异戊氧基、正己氧基、2-乙基丁氧基、苄氧基、对甲基苄氧基等，但不限于此。
在本发明中，所述环烷氧基中，上述关于环烷基的描述可以应用于环烷氧基的环烷基部分。所述环烷氧基可以是取代或未取代的。
在本发明中，所述芳基可以是单环、多环或稠环的，优选具有6至50个碳原子，更优选6至30个碳原子，特别优选6至18个碳原子，最优选具有6至10个碳原子。所述芳基可以是取代或未取代的。当所述芳基是单环芳基时，具体实例包括苯基等，但不限于此；当所述芳基是多环芳基时，具体实例包括联苯基、三联苯基等，但不限于此；当所述芳基是稠环芳基时，具体实例包括萘基、蒽基、菲基、三苯基、芘基、苝基、芴基、螺芴基、茚基、荧蒽基等，但不限于此。
在本发明中，所述亚芳基意指在芳基中具有两个键合位置的基团，即二价基团。上述关于芳基的描述可以应用于亚芳基，不同之处在于亚芳基是二价的。
在本发明中，所述杂芳基包含除碳之外的一个或更多个原子，即杂原子，并且具体地杂原子可以包括选自O、N、Se和S等中的一个或更多个原子，优选具有2至50个碳原子，更优选2至30个碳原子，特别优选2至12个碳原子，最优选2至6个碳原子。所述杂芳基可以是取代或未取代的。杂芳基可以是单环、多环或稠环的，具体实例包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、三唑基、吖啶基、菲啶基、哒嗪基、吡嗪基、吩嗪基、喹啉基、喹唑啉基、喹喔啉基、酞嗪基、异喹啉基、吲哚基、吲唑基、萘啶基、咔唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、苯并呋喃基、苯并噁唑基、噁唑基、噻唑基、二唑基、苯并噻唑基、吩噻嗪基、二苯并噻吩基、二苯并呋喃基、氮杂芴基、咔啉基、菲罗啉基等，但不限于此。
在本发明中，所述亚杂芳基意指在杂芳基中具有两个键合位置的基团，即二价基团。上述关于杂芳基的描述可以应用于亚杂芳基，不同之处在于亚杂芳基是二价的。
在本发明中，所述烯基可以是直链或支链的，优选具有2至50个碳原子，更优选2至30个碳原子，特别优选2至15个碳原子，最优选2至6个碳原子。所述烯基可以是取代或未取代的。烯基具体实例可以包括乙烯基、1-丙烯基、异丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-戊烯基、茋基、苯乙烯基等，但不限于此。
在本发明中，所述炔基可以是直链或支链的，优选具有2至50个碳原子，更优选2至30个碳原子，特别优选2至15个碳原子，最优选2至6个碳原子。所述炔基可以是取代或未取代的。炔基具体实例可以包括乙炔基、1-丙炔基、异丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-戊炔基、苯乙炔基等，但不限于此。
在本发明中，所述甲硅烷基的具体实例可以包括三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基、乙烯基二甲基甲硅烷基、丙基二甲基甲硅烷基、三苯基甲硅烷基、二苯基甲硅烷基、苯基甲硅烷基等，但不限于此。所述甲硅烷基可以是取代或未取代的。
在本发明中，所述芳氧基、芳基硫基、芳基磺酰基、芳基膦基中的芳基与上述芳基的实例相同。所述芳氧基的具体实例可以包括苯氧基、对甲苯氧基、间甲苯氧基、3,5-二甲基苯氧基、对叔丁基苯氧基、1-萘氧基、2-萘氧基、4-甲基-1-萘氧基、1-蒽氧基、9-蒽氧基、1-菲氧基、3-菲氧基、9-菲氧基等；所述芳基硫基的具体实例可以包括苯基硫基、2-甲基苯基硫基、4-叔丁基苯基硫基等；所述芳基磺酰基的具体实例可以包括苯磺酰基、对甲苯磺酰基等；然而芳氧基、芳基硫基和芳基磺酰基不限于此。
在本发明中，所述烷氧基、烷基硫基、烷基磺酰基中的烷基与上述烷基的实例相同。所述烷氧基的具体实例可以包括甲氧基、乙氧基等；所述烷基硫基的具体实例可以包括甲基硫基、乙基硫基、叔丁基硫基等；所述烷基磺酰基的具体实例可以包括甲磺酰基、乙磺酰基等；然而烷氧基、烷基硫基和烷基磺酰基不限于此。
在本发明中，所述氧化膦基的具体实例可以包括二苯基氧化膦基、二萘基氧化膦基等，但不限于此。
在本发明中，所述硼基的具体实例可以包括甲基硼基、乙基硼基、苯基硼基等，但不限于此。
本发明所述的键合形成环是指两个基团通过化学键彼此连接并任选地芳构化。如下所示例：
本发明中，键合形成的环可以为五元环或六元环或者稠合环，例如苯基、萘基、环戊烯基、环戊烷基、环己烷并苯基、喹啉基、异喹啉基、二苯并噻吩基、菲基或芘基，但不限于此。
本发明所述的“选自0～M的整数”是指所述值选自0～M的整数中的任意一个，包括0，1，2…M-2，M-1，M。例如，“j为0至5的整数”是指j为0，1，2，3，4或5；以此类推。
本发明提供了一种五元杂环衍生物，所述五元杂环衍生物如下式Ⅰ所示：
A选自下式Ⅱ表示的基团，Q选自下式Ⅲ表示的基团：
其中，X选自O、S、N-R20中的任意一种；M选自C、Si、Ge中的任意一种；
L选自单键、取代或未取代的C6-C30的亚芳基、取代或未取代的C2-C30的亚杂芳基中的任意一种；优选为单键、取代或未取代的C6-C20的亚芳基、取代或未取代的C2-C20的亚杂芳基；
Y1、Y2独立地选自O、S、C-R21R22、N-R23中的任意一种，n、m独立地选自0或1，当n或m为0时，为单键连接；
R1-R23独立地选自氢、氘、氚、氟、氯、溴、碘、氰基、硝基、羟基、羰基、酮基、酯基、酰胺基、取代或未取代的C1-C50的烷基、取代或未取代的C3-C50的环烷基、取代或未取代的C2-C50的烯基、取代或未取代的C2-C50的炔基、取代或未取代的C1-C50的烷氧基、取代或未取代的C3-C50的环烷氧基、取代或未取代的C6-C50的芳氧基、取代或未取代的C1-C50的烷基硫基、取代或未取代的C6-C50的芳基硫基、取代或未取代的C1-C50的烷基磺酰基、取代或未取代的C6-C50的芳基磺酰基、取代或未取代的C1-C50的甲硅烷基、取代或未取代的C1-C50的硼基、取代或未取代的C6-C50的芳基膦基、取代或未取代的C1-C50的氧化膦基、取代或未取代的C6-C50的芳基、取代或未取代的C2-C50的杂芳基中的任意一种，且任选地R4-R19中相邻基团可以结合成环；条件是，R1-R3、R20中的一个为单键并与L键连，R4-R19中的一个为单键并与L键连。
在本发明中，所述取代的C1-C50的烷基、取代的C3-C50的环烷基、取代的C2-C50的烯基、取代的C2-C50的炔基、取代的C1-C50的烷氧基、取代的C3-C50的环烷氧基、取代的C6-C50的芳氧基、取代的C1-C50的烷基硫基、取代的C6-C50的芳基硫基、取代的C1-C50的烷基磺酰基、取代的C6-C50的芳基磺酰基、取代的C1-C50的甲硅烷基、取代的C1-C50的硼基、取代的C6-C50的芳基膦基、取代的C1-C50的氧化膦基、取代的C6-C50的芳基、取代的C2-C50的杂芳基中的取代基独立地选自氢、氘、氰基、卤素原子、三氟甲基、C1～C10的烷基、C3～C10的环烷基、被C1-C6的烷基取代或未取代的C2～C20的杂芳基、被C1-C6的烷基取代或未取代的C6～C24的芳基，具体实例包括甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、苯基、苄基、二联苯基、三联苯基、二甲基芴基、二苯基芴基、螺芴基、菲、蒽基、萘基、噻吩基、呋喃基、吡咯基、噁唑基、咪唑基、噻唑基、吡啶基等，但不限于此，只要可以达到本发明的技术效果，则所述取代基可以为除了上述列举之外的取代基，或上述取代基的组合。所述取代基可以为一个或者多个，当所述取代基为多个时，多个取代基之间相同或者不同。
优选的，本发明的五元杂环衍生物，所述A选自下式中的任意一个：
其中，R1-R3、R20独立地选自氟、氯、溴、碘、氰基、硝基、羟基、羰基、酮基、酯基、酰胺基、取代或未取代的甲基、取代或未取代的乙基、取代或未取代的正丙基、取代或未取代的异丙基、取代或未取代的正丁基、取代或未取代的异丁基、取代或未取代的仲丁基、取代或未取代的叔丁基、取代或未取代的正戊基、取代或未取代的仲戊基、取代或未取代的叔戊基、取代或未取代的2-戊基、取代或未取代的新戊基、取代或未取代的乙烯基、取代或未取代的丙烯基、取代或未取代的丁烯基、取代或未取代的戊烯基、取代或未取代的己烯基、取代或未取代的庚烯基、取代或未取代的环丙烯基、取代或未取代的环戊烯基、取代或未取代的环己烯基、取代或未取代的环庚烯基、取代或未取代的苯乙烯基、取代或未取代的乙炔基、取代或未取代的丙炔基、取代或未取代的环丙基、取代或未取代的环戊基、取代或未取代的环己基、取代或未取代的莰烷基、取代或未取代的降冰片烷基、取代或未取代的金刚烷基、取代或未取代的苯氧基、取代或未取代的甲氧基、取代或未取代的三氟甲氧基、取代或未取代的乙氧基、取代或未取代的正丙氧基、取代或未取代的异丙氧基、取代或未取代的正丁氧基、取代或未取代的异丁氧基、取代或未取代的仲丁氧基、取代或未取代的叔丁氧基、取代或未取代的2-甲基丁氧基、取代或未取代的苯硫基、取代或未取代的甲硫基、取代或未取代的三氟甲硫基、取代或未取代的乙硫基、取代或未取代的正丙硫基、取代或未取代的异丙硫基、取代或未取代的正丁硫基、取代或未取代的异丁硫基、取代或未取代的仲丁硫基、取代或未取代的叔丁硫基、取代或未取代的2-甲基丁硫基、取代或未取代的苯基、取代未或取代的萘基、取代或未取代的蒽基、取代或未取代的荧蒽基、取代或未取代的噻吩基、取代或未取代的呋喃基、取代或未取代的苯并噻吩基、取代或未取代的苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的二苯并呋喃基、取代或未取代的芴基、取代或未取代的氮杂芴基、取代或未取代的螺芴基、取代或未取代的萘啶基、取代或未取代的吡啶基、取代或未取代的吡咯基、取代或未取代的吡嗪基、取代或未取代的吩嗪基、取代或未取代的吡唑基、取代或未取代的吲唑基、取代或未取代的哒嗪基、取代或未取代的噻唑基、取代或未取代的噁唑基、取代或未取代的咪唑基、取代或未取代的苯并噻唑基、取代或未取代的苯并噁唑基、取代或未取代的吲哚基、取代或未取代的咔唑基、取代或未取代的苯并咪唑基、取代或未取代的吖啶基、取代或未取代的菲啶基、取代或未取代的酞嗪基、取代或未取代的茚基、取代或未取代的芘基、取代或未取代的喹啉基、取代或未取代的异喹啉基、取代或未取代的菲罗啉基、取代或未取代的甲磺酰基、取代或未取代的乙磺酰基、取代或未取代的丙磺酰基、取代或未取代的丁磺酰基、取代或未取代的茋基、取代或未取代的二苯基甲硅烷基、取代或未取代的苯基甲硅烷基、取代或未取代的二苯基氧化膦基中的任意一种。
优选的，本发明的五元杂环衍生物，所述R1-R3、R20独立地选自氰基、甲基或下式中的任意一种：
其中，R24选自氢、氘、氚、氟、氯、溴、碘、氰基、硝基、羟基、羰基、酮基、酯基、酰胺基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、仲戊基、叔戊基、2-戊基、新戊基、乙烯基、丙烯基、丁烯基、戊烯基、己烯基、庚烯基、环丙烯基、环戊烯基、环己烯基、苯乙烯基、乙炔基、丙炔基、环丙基、环戊基、环己基、苯基、苯氧基、苯硫基、萘基、蒽基、二联苯基、三联苯基、噻吩基、呋喃基、苯并噻吩基、苯并呋喃基、二苯并噻吩基、二苯并呋喃基、吲哚基、咔唑基、9,9-二甲基芴基、9,9-二苯基芴基、吡啶基、吖啶基、菲啶基、吡咯基、吡嗪基、哒嗪基、噻唑基、噁唑基、咪唑基、吩嗪基、吡唑基、吲唑基、苯并噻唑基、苯并噁唑基、苯并咪唑基、喹啉基、异喹啉基、菲罗啉基、萘啶基、酞嗪基、茚基、芘基、莰烷基、降冰片烷基、金刚烷基、甲硫基、三氟甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、2-甲基丁硫基、荧蒽基、氮杂芴基、甲磺酰基、乙磺酰基、丙磺酰基、丁磺酰基、茋基、二苯基甲硅烷基、苯基甲硅烷基、二苯基氧化膦基中的任意一种，j为0至5的整数，当j为2或更大时，各个R24基团彼此相同或不同，且任选地相邻的基团可以结合成环。
优选的，本发明的五元杂环衍生物，所述A选自下式中的任意一个：
其中，j为0至5的整数，多个j同时存在时，各个j彼此相同或不同，多个R24同时存在时，各个R24基团彼此相同或不同，且任选地相邻的R24基团可以结合成环。
优选的，本发明的五元杂环衍生物，所述Q选自下式中任意一个：
其中，R4-R19独立地选自氢、氘、氚、氟、氯、溴、碘、氰基、硝基、羟基、羰基、酮基、酯基、酰胺基、甲基、乙基、正丙基、异丙基、异丁基、仲丁基、叔丁基、异戊基、新戊基、叔戊基、乙烯基、苯乙烯基、丙烯基、乙炔基、丙炔基、苯氧基、苯硫基、甲氧基、三氟甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、2-甲基丁氧基、甲硫基、三氟甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、2-甲基丁硫基、环丙基、环戊基、环己基、苯基、萘基、蒽基、二联苯基、三联苯基、噻吩基、呋喃基、苯并噻吩基、苯并呋喃基、二苯并噻吩基、二苯并呋喃基、吲哚基、咔唑基、9,9-二甲基芴基、9,9-二苯基芴基、吡啶基、吡嗪基、哒嗪基、噻唑基、噁唑基、咪唑基、苯并噻唑基、苯并噁唑基、苯并咪唑基、喹啉基、异喹啉基、菲罗啉基、吡啶并吲哚基、萘啶基、酞嗪基、茚基、芘基、吖啶基、菲啶基、吩嗪基、吡唑基、吲唑基、荧蒽基、氮杂芴基、甲磺酰基、乙磺酰基、丙磺酰基、丁磺酰基、茋基、二苯基甲硅烷基、苯基甲硅烷基、二苯基氧化膦基中的任意一种；
R21-R23独立地选自氟、氯、溴、碘、氰基、硝基、羟基、羰基、酮基、酯基、酰胺基、甲基、乙基、正丙基、异丙基、异丁基、仲丁基、叔丁基、异戊基、新戊基、叔戊基、乙烯基、苯乙烯基、丙烯基、环丙基、环戊基、环己基、苯氧基、苯硫基、苯基、萘基、蒽基、二联苯基、三联苯基、噻吩基、呋喃基、苯并噻吩基、苯并呋喃基、二苯并噻吩基、二苯并呋喃基、吲哚基、咔唑基、9,9-二甲基芴基、9,9-二苯基芴基、吡啶基、吡嗪基、哒嗪基、噻唑基、噁唑基、咪唑基、苯并噻唑基、苯并噁唑基、苯并咪唑基、喹啉基、异喹啉基、菲罗啉基、茋基、二苯基甲硅烷基、苯基甲硅烷基、二苯基氧化膦基中的任意一种。
优选的，本发明的五元杂环衍生物，所述L选自单键或下式任意一个：
其中，R25选自氢、氘、氚、氟、氯、溴、碘、氰基、取代或未取代的甲基、取代或未取代的乙基、取代或未取代的正丙基、取代或未取代的异丙基、取代或未取代的异丁基、取代或未取代的仲丁基、取代或未取代的叔丁基、取代或未取代的异戊基、取代或未取代的新戊基、取代或未取代的叔戊基、取代或未取代的苯基中的任意一种，w、i、f独立地为0至4的整数，b、d独立地为0至3的整数，当w、i、f、b、d为1或者更大时，各个R25基团彼此相同或不同。
最优选，本发明的五元杂环衍生物，选自如下所示化学结构中的任意一个：
本发明合成路线如下:
Q-Br和
通过碳碳偶联反应得到
上述中间产物和A-L-Br，通过碳碳偶联反应得到A-L-Q。
所述Q、A、L如上述定义。
本发明还提供了一种有机电致发光器件，包括阳极、阴极以及有机功能层，所述有机功能层包括电子传输层和/或空穴阻挡层，所述电子传输层和/或空穴阻挡层含有至少一种本发明所述的五元杂环衍生物。
优选的，本发明还提供了一种照明或显示元件，所述照明或显示元件包括本发明所述的有机电致发光器件。
本发明所述的有机电致发光器件的有机功能层可以具有单层结构，或者具有两层以上的多层结构。本发明的有机电致发光器件的有机功能层可以包含空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层、覆盖层或者置于阳极和空穴注入层之间的缓冲层中的任意一层或者任意多层。
本发明所述的有机电致发光器件中，本发明化合物可以用于上述有机功能层中的任意一层或者任意多层，优选为在电子传输层和/或空穴阻挡层含有。含量没有特别限制，可以根据需要适当调整。
优选的，本发明所述的阳极材料，可以选择如下材料中的一种或者多种：铜、金、银、铁、铬、镍、锰、钯、铂等及它们的合金；金属氧化物例如：氧化铟、氧化锌、氧化铟锡(ITO)、氧化铟锌(IZO)、氧化铝锌、ITO-Ag-ITO等；导电性聚合物例如：聚苯胺、聚吡咯、聚(3-甲基噻吩)等，但不限于此。除了以上材料及其组合之外，阳极材料还可包括其他已知的适合做阳极的材料。
优选的，本发明所述的空穴注入材料具有较好的空穴注入性能，可以选择如下材料中的一种或者多种：三氧化钼、氧化银、三氧化钨、氧化钌、氧化镍、氧化铜、二氧化钛、三氧化二铝、酞菁铜(II)(简称:CuPc)、氧钛酞菁(简称:TiOPC)、2,3,6,7,10,11-六氰基-1,4,5,8,9,12-六氮杂苯并菲(简称HAT-CN)、4,4',4”-三(2-萘基苯基氨基)三苯基胺(简称:2T-NATA)等，但不限于此。其可以是单一物质构成的单一结构，也可是不同物质形成的单层结构或多层结构。
优选的，本发明所述的空穴传输材料具有较好的空穴传输性能，可以选自如下材料中的一种或者多种：4,4',4”-三(N,N-二苯基氨基)三苯胺(简称:TDATA)、N,N'-二苯基-N,N'-二菲-9-基-4,4'-联苯二胺(简称:PPD)、N,N'-二(萘-1-基)-N,N'-二(苯基)-2,2'-二甲基联苯胺(简称:α-NPD)、N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺(简称:NPB)等，但不限于此。其可以是单一物质构成的单一结构，也可是不同物质形成的单层结构或多层结构。
优选的，本发明所述的电子阻挡层材料，可以选自如下材料中的一种或者多种：4,4',4”-三(N,N-二苯基氨基)三苯胺(简称:TDATA)、N,N'-二苯基-N,N'-二(3-甲基苯基)-1,1'-联苯-4,4'-二胺(简称:TPD)、4,4'-环己基二[N,N-二(4-甲基苯基)苯胺](简称:TAPC)、2,2,7,7-四(二苯基氨基)-9,9-螺二芴(简称:Spiro-TAD)等，但不限于此。其可以是单一物质构成的单一结构，也可是不同物质形成的单层结构或多层结构。
优选的，本发明所述的发光层，可以是主客体的形式、可以是包含一种材料或可以包含两种以上的混合材料，本发明所述主体材料可以选自如下材料：4,4'-二(9-咔唑)联苯(CBP)、9,10-二(2-萘基)蒽(ADN)、9,9'-(1,3-苯基)二-9H-咔唑(mCP)、4,4',4”-三(咔唑-9-基)三苯胺(TCTA)、9,10-二(1-萘基)蒽(α-AND)、1,3,5-三(9-咔唑基)苯(TCP)等，但不限于此。发光层主体材料还可包括其他已知的适合做发光层的材料，其可以是单一物质构成的单一结构，也可是不同物质形成的单层结构或多层结构。
优选的，本发明所述的发光层客体材料可以选自如下材料：4,4'-二[4-(二苯氨基)苯乙烯基]联苯(BDAVBi)、4,4'-二[4-(二对甲苯基氨基)苯乙烯基]联苯(DPAVBi)、4,4'-双(9-乙基-3-咔唑乙烯基)-1,1'-联苯(BCzVBi)、二(4,6-二氟苯基吡啶-C2,N)吡啶甲酰合铱(FIrpic)、三(2-苯基吡啶)合铱(Ir(ppy)3)、乙酰丙酮酸二(2-苯基吡啶)铱(Ir(ppy)2(acac))、三[1-苯基异喹啉-C2,N]铱(III)(Ir(piq)3)、二(1-苯基异喹啉)(乙酰丙酮)合铱(Ir(piq)2(acac))等，但不限于此。发光层客体材料还可包括其他已知的适合做发光层的材料。
优选的，本发明所述的空穴阻挡层材料，可以选自如下材料中的一种或者多种：本发明化合物、2,9-二甲基-4,7-联苯-1,10-菲罗啉(简称:BCP)、1,3,5-三(N-苯基-2-苯并咪唑)苯(简称:TPBi)、三(8-羟基喹啉)铝(简称:Alq3)、8-羟基喹啉锂(简称:Liq)、双(2-甲基-8-羟基喹啉-N1,O8)-(1,1'-联苯-4-羟基)铝(简称:BAlq)等，但不限于此。其可以是单一物质构成的单一结构，也可是不同物质形成的单层结构或多层结构。
优选的，本发明所述的电子传输层材料，可以选自如下材料中的一种或者多种：本发明化合物、噁二唑衍生物、2,9-二甲基-4,7-联苯-1,10-菲罗啉(简称:BCP)、1,3,5-三(N-苯基-2-苯并咪唑)苯(简称:TPBi)、三(8-羟基喹啉)铝(简称:Alq3)、8-羟基喹啉锂(简称:Liq)、4,7-二苯基-1,10-菲罗啉(简称:Bphen)、3-(联苯-4-基)-5-(4-叔丁基苯基)-4-苯基-4H-1,2,4-三唑(简称:TAZ)、双(2-甲基-8-羟基喹啉-N1,O8)-(1,1'-联苯-4-羟基)铝(简称:BAlq)等，但不限于此。其可以是单一物质构成的单一结构，也可是不同物质形成的单层结构或多层结构。
优选的，本发明所述的电子注入材料，可以选自如下材料中的一种或者多种：Li、Na、K、Rb、Cs、Be、Mg、Ca、Sr、Ba、氟化锂、氟化钠、氟化钾、氟化铷、氟化铯、氟化镁、氟化钙、8-羟基喹啉锂等，但不限于此。其可以是单一物质构成的单一结构，也可是不同物质形成的单层结构或多层结构。
优选的，本发明所述的阴极材料，可以选自如下材料中的一种或者多种：铜、金、银、铁、铬、镍、锰、钯、铂等及它们的合金；多层金属材料例如：LiF/Al、Mg/Ag、Li/Al、LiO2/Al、BaF2/Al等，但不限于此。除以上材料及其组合之外，阴极材料还可包括其他已知的适合做阴极的材料。
优选的，本发明所述的覆盖层材料，可以选自如下材料中的一种或者多种：LaB6、ZTO、Al2O3、MgO、TiO2、MgF2、12CaO·7Al2O3、SiO2、SiNx、SnO2、ZnO、ZrO2、WO3、MoO3、NPB、TPD、Alq3、CBP、TPBi等，但不限于此。
本发明的有机电致发光器件的器件结构优选为：
基板/阳极/空穴传输层/发光层/电子传输层/阴极；
基板/阳极/空穴传输层/发光层/电子传输层/电子注入层/阴极；
基板/阳极/空穴注入层/空穴传输层/发光层/电子传输层/阴极；
基板/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；
基板/阳极/空穴注入层/空穴传输层/电子阻挡层/发光层/电子传输层/电子注入层/阴极；
基板/阳极/空穴注入层/空穴传输层/发光层/空穴阻挡层/电子传输层/电子注入层/阴极；
基板/阳极/空穴注入层/空穴传输层/电子阻挡层/发光层/空穴阻挡层/电子传输层/电子注入层/阴极；
基板/阳极/空穴传输层/发光层/电子传输层/阴极/覆盖层；
基板/阳极/空穴传输层/发光层/电子传输层/电子注入层/阴极/覆盖层；
基板/阳极/空穴注入层/空穴传输层/发光层/电子传输层/阴极/覆盖层；
基板/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/覆盖层；
基板/阳极/空穴注入层/空穴传输层/发光层/空穴阻挡层/电子传输层/电子注入层/阴极/覆盖层；
基板/阳极/空穴注入层/空穴传输层/电子阻挡层/发光层/电子传输层/电子注入层/阴极/覆盖层；
基板/阳极/空穴注入层/空穴传输层/电子阻挡层/发光层/空穴阻挡层/电子传输层/电子注入层/阴极/覆盖层等，但有机电致发光器件的结构不限于此。
本发明所述的有机电致发光器件可以使用已知材料通过已知方法制备，有机电致发光器件中各层的制备形成方法，没有特别限制。
本发明所述的有机发电致光器件可广泛应用于面板显示、照明、OLED、太阳能电池、有机感光体或有机薄膜晶体管、指示牌、信号灯等领域。
实施例
将通过合成实施例和器件实施例来更加具体的描述本发明，但是本发明的范围并不限于下列合成实施例和器件实施例。
化合物的制备及表征
原料、试剂以及表征设备的说明：
本发明所用的原料及试剂均为试剂纯；
质谱使用英国沃特斯G2-Si四极杆串联飞行时间高分辨质谱仪，氯仿为溶剂；
元素分析使用德国Elementar公司的Vario EL cube型有机元素分析仪，样品质量为5～10mg；
核磁共振(1HNMR)使用Bruker-510型核磁共振谱仪(德国Bruker公司)，500MHz，CDCl3为溶剂，TMS为内标。
中间体a-1的合成
将原料2(21.02g，0.10mol)、原料3(34.40g，0.20mol)、原料1(21.22g，0.20mol)、0.07mol的DABCO、0.30mol的叔丁醇钠的混合物溶于含乙醇的烧瓶中，65℃下搅拌15h，反应完成后，反应混合物用水稀释，过滤，洗涤并干燥。柱层析分离提纯(洗脱剂为石油醚∶DCM＝10∶1～1∶1)，(收率89％，HPLC检测固体纯度≧99.5％)。
a-2至a-3与a-1方法相同，按照制备中间体a-1的方法制备a-2至a-3，原料及收率如下表1所示：
表1
中间体a-4的合成
将原料4(45.14g，0.10mol)、原料5(28.29g，0.10mol)、0.30mol的K2CO3溶于含甲苯/乙醇/水的烧瓶中，室温搅拌下置换氮气后加入0.001mol的Pd(PPh3)4。搅拌回流反应8小时，TLC监控反应终点。降至室温后分液，水相用甲苯萃取，合并有机相，无水硫酸钠干燥，减压旋干溶剂，柱层析分离提纯(洗脱剂为石油醚∶DCM＝10∶1～1∶1)，(收率80％，HPLC检测固体纯度≧99.6％)。
a-5至a-6与a-4方法相同，按照制备中间体a-4的方法制备a-5至a-6，原料及收率如下表2所示：
表2
合成实施例1：化合物1的合成:
将b-1(39.40g，0.1mol)、f(76.20g，0.3mol)、KOAc(11.78g，0.12mol)溶于含1,4-二氧六环(500mL)的烧瓶中，室温搅拌下置换氮气后加入Pd(dppf)Cl2(0.731g，0.001mol)。搅拌回流反应8小时，TLC监控反应终点。减压旋除溶剂，用DCM溶解后加入100mL纯水洗涤，分液，水相用DCM萃取，合并有机相，无水硫酸钠干燥，柱层析分离提纯(洗脱剂为DCM)，得到中间体d-1(39.81g，收率90％，检测固体纯度≧99.8％)。
将中间体d-1(21.37g，0.05mol)、a-1(22.57g，0.05mol)、K2CO3(20.73g，0.15mol)溶于含甲苯/乙醇/水的烧瓶中，室温搅拌下置换氮气后加入Pd(PPh3)4(0.58g，0.0005mol)。加毕，搅拌回流反应8小时，TLC监控反应终点。降至室温后分液，水相用甲苯萃取，合并有机相，无水硫酸钠干燥，减压旋干溶剂，柱层析分离提纯(洗脱剂为石油醚∶DCM＝10∶1～1∶1)，得到化合物1(26.79g，检测固体纯度≧99.3％)。质谱m/z：686.2718(理论值：686.2722)。理论元素含量(％)C52H34N2：C，90.93；H，4.99；N，4.08。实测元素含量(％)C，90.94；H，4.51；N，4.05。上述结果证实获得产物为目标产品。
合成实施例2：化合物2的合成
将合成实施例1中的b-1替为等摩尔量的b-2，其他合成过程同合成实施例1，得到化合物2(26.36g，检测固体纯度≧99.6％)。质谱m/z：702.2663(理论值：702.2671)。理论元素含量(％)C52H34N2O：C，88.86；H，4.88；N，3.99；O，2.28。实测元素含量(％)C，88.89；H，4.86；N，3.97；O，2.29。1H NMR(500MHz，CDCl3)δ8.04(d,1H),7.96(s,1H),7.92(dd,3H),7.81(dd,1H),7.77–7.74(m,2H),7.64(dd,1H),7.58–7.54(m,3H),7.52–7.39(m,12H),7.33–7.31(m,2H),7.29–7.24(m,2H),7.21–7.18(m,2H),7.08–7.02(m,2H),6.97–6.94(m,2H)。上述结果证实获得产物为目标产品。
合成实施例3：化合物18的合成
将合成实施例1中的b-1替换为等摩尔量的b-3，其他合成过程同合成实施例1，即可得到化合物18(26.60g，检测固体纯度≧99.5％)。质谱m/z：718.2436(理论值：718.2443)。理论元素含量(％)C52H34N2S：C，86.88；H，4.77；N，3.90。实测元素含量(％)C，86.85；H，4.79；N，3.93。1H NMR(500MHz，CDCl3)δ8.09(s,1H),8.03(d,1H),7.97–7.91(m,3H),7.86–7.76(m,5H),7.70(dd,1H),7.61(td,1H),7.59–7.54(m,2H),7.52–7.40(m,12H),7.31–7.27(m,3H),7.25–7.18(m,4H),7.05–7.01(m,2H)。上述结果证实获得产物为目标产品。
合成实施例4：化合物93的合成
将合成实施例1中的b-1替换为等摩尔量的b-5，a-1替换为等摩尔量的a-3，其他合成过程同合成实施例1，即可得到化合物93(25.15g，检测固体纯度≧99.1％)。质谱m/z：728.3188(理论值：728.3191)。理论元素含量(％)C55H40N2：C，90.63；H，5.53；N，3.84。实测元素含量(％)C，90.60；H，5.55；N，3.85。1H NMR(500MHz，CDCl3)δ7.94–7.92(m,2H),7.90(dd,2H),7.83(d,2H),7.81(s,1H),7.80–7.78(m,2H),7.59–7.55(m,6H),7.53–7.46(m,10H),7.44–7.40(m,6H),7.34–7.30(m,2H),1.76(d,6H).。上述结果证实获得产物为目标产品。
合成实施例5：化合物112的合成
将合成实施例1中的b-1替换为等摩尔量的b-4，a-1替换为等摩尔量的a-2，其他合成过程同合成实施例1，即可得到化合物112(28.01g，检测固体纯度≧99.3％)。质谱m/z：777.3140(理论值：777.3144)。理论元素含量(％)C58H39N3：C，89.55；H，5.05；N，5.40。实测元素含量(％)C，89.52；H，5.06；N，5.42。1H NMR(500MHz，CDCl3)δ8.06(d,1H),8.04(s,1H),7.94(dd,1H),7.85(dd,1H),7.76–7.67(m,3H),7.67–7.51(m,5H),7.51–7.37(m,13H),7.37–7.28(m,3H),7.28–7.16(m,4H),7.14–7.09(m,2H),7.06–6.96(m,3H),7.04–6.91(m,2H).。上述结果证实获得产物为目标产品。
合成实施例6：化合物147的合成
将合成实施例1中的b-1替换为等摩尔量的b-2，a-1替换为等摩尔量的a-4，其他合成过程同合成实施例1，即可得到化合物147(26.09g，检测固体纯度≧99.3％)。质谱m/z：778.2979(理论值：778.2984)。理论元素含量(％)C58H38N2O：C，89.43；H，4.92；N，3.60。实测元素含量(％)C，89.46；H，4.89；N，3.63。上述结果证实获得产物为目标产品。
合成实施例7：化合物300的合成
将合成实施例1中的b-1替换为等摩尔量的b-6，其他合成过程同合成实施例1，即可得到化合物300(25.65g，检测固体纯度≧99.5％)。质谱m/z：702.2669(理论值：702.2671)。理论元素含量(％)C52H34N2O：C，88.86；H，4.88；N，3.99。实测元素含量(％)C，88.89；H，4.85；N，3.97。上述结果证实获得产物为目标产品。
合成实施例8：化合物308的合成
将合成实施例1中的b-1替换为等摩尔量的b-7，其他合成过程同合成实施例1，即可得到化合物308(30.36g，检测固体纯度≧99.4％)。质谱m/z：798.3971(理论值：798.3974)。理论元素含量(％)C60H50N2：C，90.19；H，6.31；N，3.51。实测元素含量(％)C，90.16；H，6.33；N，3.52。上述结果证实获得产物为目标产品。
合成实施例9：化合物351的合成
在氮气保护下，向一干燥洁净的250mL的三口瓶中，加入m(24.91g，0.10mol)、150mL无水四氢呋喃，并于室温下搅拌溶解。将体系冷却至-78℃，搅拌加入n(30.91g，0.10mol)，加完后移去冷浴，反应自行回温至室温并继续搅拌过夜。反应结束后水洗，干燥，所得固体转移到装有回流冷凝管的250mL单口瓶中，加入100mL冰醋酸并加热回流，滴加3mL浓盐酸，继续回流反应过夜。反应结束后关闭加热，冷却至室温，反应液倒入冰水中，过滤。粗品经柱层析进一步纯化(石油醚：二氯甲烷＝5：1(V/V))后得到b-9(37.37g，收率81％，检测固体纯度≧99.4％)。
将合成实施例1中的b-1替换为等摩尔量的b-9，a-1替换为等摩尔量的a-5，其他合成过程同合成实施例1，即可得到化合物351(26.11g，收率63％，检测固体纯度≧99.0％)。质谱m/z：828.3135(理论值：828.3141)。理论元素含量(％)C62H40N2O：C，89.83；H，4.86；N，3.38。实测元素含量(％)C，89.86；H，4.88；N，3.36。1H NMR(500MHz，CDCl3)δ9.62(dd,1H),9.01(d,1H),8.32–8.30(m,1H),8.25–8.24(m,1H),8.23(s,1H),8.14–7.99(m,3H),7.86(d,4H),7.75(d,2H),7.69(d,2H),7.58–7.52(m,2H),7.52–7.45(m,5H),7.45(d,1H),7.44–7.39(m,4H),7.37(d,1H),7.36–7.24(m,3H),7.24–7.15(m,3H),7.01–6.98(m,1H),6.75(dd,1H),6.71–6.56(m,3H)。上述结果证实获得产物为目标产品。
合成实施例10：化合物363的合成
将合成实施例1中的b-1替换为等摩尔量的b-10，a-1替换为等摩尔量的a-6，其他合成过程同合成实施例1，即可得到化合物363(25.56g，检测固体纯度≧99.2％)。质谱m/z：762.3031(理论值：762.3035)。理论元素含量(％)C58H38N2：C，91.31；H，5.02；N，3.67。实测元素含量(％)C，91.28；H，5.03；N，3.69。上述结果证实获得产物为目标产品。
合成实施例11：化合物376的合成
将合成实施例1中的b-1替换为等摩尔量的b-11，a-1替换为等摩尔量的a-4，其他合成过程同合成实施例1，即可得到化合物376(28.00g，检测固体纯度≧99.4％)。质谱m/z：874.4279(理论值：874.4287)。理论元素含量(％)C66H54N2：C，90.58；H，6.22；N，3.20。实测元素含量(％)C，90.56；H，6.25；N，3.19。上述结果证实获得产物为目标产品。
器件性能
有机材料以及设备的说明：
本发明所用的有机材料都是经过升华，纯度在99.99％以上；
驱动电压、发光效率的测试是通过测试软件、计算机、美国Keithley公司生产的K2400数字源表和美国Photo Research公司的PR788光谱扫描亮度计组成一个联合IVL测试系统来测试；
寿命的测试采用McScience公司的M6000 OLED寿命测试系统，测试环境为大气环境，温度为室温。
对比例1：有机电致发光器件的制备
在异丙醇中，对粘附了ITO电极的透明玻璃基板进行清洗透明的OLED器件基板1上的ITO阳极层，分别用去离子水、丙酮、乙醇超声清洗各15分钟，然后在等离子体清洗器中处理2分钟，120℃烘干。将准备好的ITO透明电极上真空蒸镀50nm的HAT-CN作为空穴注入层，在空穴注入层上，通过真空蒸镀方式蒸镀30nm的NPB作为空穴传输层，在空穴传输之上蒸镀发光层，CBP和BCzVBi的重量比为90:10作为发光层，发光层的蒸镀厚度为30nm，在发光层上，真空蒸镀10nm的BAlq作为空穴阻挡层，在空穴阻挡层上，真空蒸镀40nm的化合物TPBi作为电子传输层，在电子传输层上，通过真空蒸镀方式蒸镀1nm的LiF作为电子注入层，在电子注入层上蒸镀120nm的Al膜作为阴极，从而形成有机电致发光器件。
实施例1：有机电致发光器件的制备
将对比例1中的TPBi换成化合物18，其他步骤与对比例1相同。
实施例2：有机电致发光器件的制备
将对比例1中的TPBi换成化合物112，其他步骤与对比例1相同。
实施例3：有机电致发光器件的制备
将对比例1中的TPBi换成化合物147，其他步骤与对比例1相同。
实施例4：有机电致发光器件的制备
将对比例1中的TPBi换成化合物351，其他步骤与对比例1相同。
实施例5：有机电致发光器件的制备
将对比例1中的TPBi换成化合物376，其他步骤与对比例1相同。
实施例6：有机电致发光器件的制备
将对比例1中的BAlq换成化合物2，其他步骤与对比例1相同。
实施例7：有机电致发光器件的制备
将对比例1中的BAlq换成化合物93，其他步骤与对比例1相同。
实施例8：有机电致发光器件的制备
将对比例1中的BAlq换成化合物308，其他步骤与对比例1相同。
实施例9：有机电致发光器件的制备
将对比例1中的BAlq换成化合物363，其他步骤与对比例1相同。
实施例10：有机电致发光器件的制备
将对比例1中的TPBi换成化合物1，BAlq换成化合物2，其他步骤与对比例1相同。
实施例11：有机电致发光器件的制备
将对比例1中的TPBi、BAlq换成化合物2，其他步骤与对比例1相同。
实施例12：有机电致发光器件的制备
将对比例1中的TPBi、BAlq换成化合物18，其他步骤与对比例1相同。
实施例13：有机电致发光器件的制备
将对比例1中的TPBi、BAlq换成化合物112，其他步骤与对比例1相同。
实施例14：有机电致发光器件的制备
将对比例1中的TPBi换成化合物351，BAlq换成化合物308，其他步骤与对比例1相同。
实施例15：有机电致发光器件的制备
将对比例1中的TPBi换成化合物376，BAlq换成化合物18，其他步骤与对比例1相同。
对比例2：有机电致发光器件的制备
将对比例1中的TPBi换成化合物E1，其他步骤与对比例1相同。
对比例3：有机电致发光器件的制备
将对比例1中的TPBi换成化合物E2，其他步骤与对比例1相同。
对比例4：有机电致发光器件的制备
将对比例1中的TPBi换成化合物E3，其他步骤与对比例1相同。
对比例5：有机电致发光器件的制备
将对比例1中的TPBi换成化合物E4，其他步骤与对比例1相同。
对比例6：有机电致发光器件的制备
将对比例1中的BAlq换成化合物E9，其他步骤与对比例1相同。
对比例7：有机电致发光器件的制备
将对比例1中的BAlq换成化合物E5，其他步骤与对比例1相同。
对比例8：有机电致发光器件的制备
将对比例1中的BAlq换成化合物E6，其他步骤与对比例1相同。
对比例9：有机电致发光器件的制备
将对比例1中的BAlq换成化合物E8，其他步骤与对比例1相同。
对比例10：有机电致发光器件的制备
将对比例1中的TPBi、BAlq换成化合物BCP，其他步骤与对比例1相同。
对比例11：有机电致发光器件的制备
将对比例1中的TPBi换成化合物E1，BAlq换成化合物E7，其他步骤与对比例1相同。
对比例12：有机电致发光器件的制备
将对比例1中的TPBi换成化合物E4，BAlq换成化合物E3，其他步骤与对比例1相同。
对比例13：有机电致发光器件的制备
将对比例1中的TPBi换成化合物E8，BAlq换成化合物E9，其他步骤与对比例1相同。
对比例14：有机电致发光器件的制备
将对比例1中的TPBi、BAlq换成化合物E7，其他步骤与对比例1相同。
通过上述实施例1-15和对比例1-14方法制造的有机发光器件在10mA/cm2的电流密度下测量驱动电压和发光效率，并且在20mA/cm2的电流密度下测量初始亮度的90％的时间(T90)，结果见表3所示。
表3
由表3的结果可以看出，实施例1-15与对比例1-14进行比较，含有本发明五元杂环衍生物的有机发光器件的驱动电压、效率和寿命方面明显优于对比例中化合物，本发明的五元杂环衍生物是性能良好的有机电致发光材料。
本申请虽然以较佳实施例公开如上，但并不是用来限定权利要求，任何本领域技术人员在不脱离本申请构思的前提下，都可以做出若干可能的变动和修改，因此本申请的保护范围应当以本申请权利要求所界定的范围为准。
Claims (5)
1.一种五元杂环衍生物，其特征在于，所述五元杂环衍生物如下式Ⅰ所示：
所述A选自下式中的任意一个：
所述R1-R3、R20独立地选自下式中的任意一种：
R24选自氢、氘、氚、氰基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、环丙基、环戊基、环己基、苯基、吡啶基中的任意一种，j为0至5的整数，当j为2或更大时，各个R24基团彼此相同或不同，且任选地相邻的基团可以结合成苯环；
所述Q选自下式中任意一个：
R4-R19独立地选自氢、氘、氚、氰基、甲基、乙基、正丙基、异丙基、异丁基、仲丁基、叔丁基、环丙基、环戊基、环己基中的任意一种；且任选地R4-R19中相邻基团可以结合成苯环；条件是，R4-R19中的一个为单键并与L键连；
R21-R22独立地选自甲基、乙基、正丙基、异丙基、异丁基、仲丁基、叔丁基、环丙基、环戊基、环己基、苯基中的任意一种；
R23独立地选自苯基、萘基、二联苯基中的任意一种；
所述L选自单键或下式任意一个：
R25选自氢、氘、氚、氰基、甲基、乙基、正丙基、异丙基、异丁基、仲丁基、叔丁基中的任意一种，w、i、f独立地为0至4的整数，b、d独立地为0至3的整数，当w、i、f、b、d为1或者更大时，各个R25基团彼此相同或不同。
2.根据权利要求1中所述一种五元杂环衍生物，其特征在于，所述A选自下式中的任意一个：
j为0至5的整数，多个j同时存在时，各个j彼此相同或不同，多个R24同时存在时，各个R24基团彼此相同或不同，且任选地相邻的R24基团可以结合成苯环。
3.一种五元杂环衍生物，其特征在于，所述五元杂环衍生物选自如下所示化学结构中的任意一个：
4.一种有机电致发光器件，包括阳极、阴极以及有机功能层，其特征在于，所述有机功能层包括电子传输层和/或空穴阻挡层，所述电子传输层和/或空穴阻挡层含有至少一种权利要求1-3任一项所述的五元杂环衍生物。
5.一种照明或显示元件，其特征在于，所述照明或显示元件包括权利要求4所述的有机电致发光器件。
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