CN110343107B - 含氮杂环化合物及其应用和有机电致发光器件 - Google Patents
含氮杂环化合物及其应用和有机电致发光器件 Download PDFInfo
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- CN110343107B CN110343107B CN201810308209.2A CN201810308209A CN110343107B CN 110343107 B CN110343107 B CN 110343107B CN 201810308209 A CN201810308209 A CN 201810308209A CN 110343107 B CN110343107 B CN 110343107B
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- heterocyclic compound
- nitrogen
- containing heterocyclic
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- -1 Nitrogen-containing heterocyclic compound Chemical class 0.000 title claims abstract description 88
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- 239000000758 substrate Substances 0.000 claims description 11
- 230000005525 hole transport Effects 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 6
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
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- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
- 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 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
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 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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Abstract
本公开涉及一种含氮杂环化合物,具有如下通式(1)所示的结构:
Description
技术领域
本公开涉及有机电致发光材料领域,具体地,涉及一种含氮杂环化合物及其应用和有机电致发光器件。
背景技术
随着OLED技术在照明和显示两大领域的不断推进,人们对于影响OLED器件性能的高效有机材料的研究更加关注,一个效率好寿命长的有机电致发光器件通常是器件结构与各种有机材料的优化搭配的结果。在最常见的OLED器件结构里,通常包括以下种类的有机材料:空穴注入材料、空穴传输材料、电子传输材料,以及各色的发光材料(染料或者掺杂客体材料)和相应的主体材料等。
发光材料可以发出蓝色,绿色,红色和黄色等几种光,为了提高发光层的发光效率,可以在发光层中掺入具有更高量子效率的发光材料。已知激发子具有将能量转移给重新组合部位附近材料中具有更小带隙材料的倾向。因此掺杂剂选自比主体材料具有更高的量子效率和带隙的材料。否则,激发子的能量将转移到主体材料,并因此影响发射效率。
发明内容
本公开的目的是提供一种含氮杂环化合物及其应用和有机电致发光器件,该含氮杂环化合物应用于有机电致发光器件中,能够降低有机电致发光器件的工作电压、提高电流效率。
为了实现上述目的,本公开第一方面提供一种含氮杂环化合物,该含氮杂环化合物具有如下通式(1)所示的结构:
其中,R1、R2、R3、R4、R5、R6、R7、R3’、R4’、R5’、R6’和R7’各自独立地选自氢、C1~C10烷基、C1~C10烷氧基、C1~C10硅烷基、卤素、氰基和式(2)所示基团中的至少一种,且R1、R2、R3、R4、R5、R6、R7、R3’、R4’、R5’、R6’和R7’不同时为氢;
其中,*为连接位点;L选自单键、取代或未取代的C6~C30亚芳基和取代或未取代的C2~C30亚杂芳基中的一种;Ar选自取代或未取代的C6~C30的芳基,取代或未取代的C2~C30的杂芳基和取代或未取代的C6~C30的芳胺中的一种;
所述取代的C6~C30亚芳基、取代的C2~C30亚杂芳基、取代的C6~C30的芳基、取代的C2~C30的杂芳基和取代的C6~C30的芳胺中的取代基各自独立地选自卤素、C1~C10的烷基、C3~C10的环烷基、C2~C10烯基、C1~C6的烷氧基、C1~C6的硫代烷氧基、C6~C30的芳基和C3~C30的杂芳基中的至少一种。
本公开第二方面提供上述第一方面的含氮杂环化合物在制备有机电致发光器件中的应用。
本公开第三方面提供一种有机电致发光器件,包括基板、阳极层、阴极层、以及介于阳极层与阴极层之间的至少一层有机功能层,所述有机功能层包括空穴注入层、空穴传输层、有机发光层、电子传输层以及电子注入层,所述有机发光层的磷光主体材料和/或电子传输层含有上述第一方面所述的含氮杂环化合物。
本公开的含氮杂环化合物中,母核结构含有两个N原子,因而具有缺电特性,并且其具有刚性的平面结构和大的π共轭体系,有利于电子传输,可以作为高迁移率有机半导体材料应用于有机光电领域,能够降低发光器件的驱动电压导致、提高发光效率。该含氮杂环化合物应用范围广,当母核上连接上给电子基团时,其发射峰的峰值在绿光范围内,可以作为绿色磷光主体应用在有机电致发光器件中;当母核上连接拉电子基团时,其电子亲和势增加,生成的化合物更有利于电子的传输,可以作为电子传输材料应用在有机电致发光器件中。
本公开的其他特征和优点将在随后的具体实施方式部分予以详细说明。
具体实施方式
以下对本公开的具体实施方式进行详细说明。应当理解的是,此处所描述的具体实施方式仅用于说明和解释本公开,并不用于限制本公开。
本公开第一方面提供一种含氮杂环化合物,该含氮杂环化合物具有如下通式(1)所示的结构:
其中,R1、R2、R3、R4、R5、R6、R7、R3’、R4’、R5’、R6’和R7’各自独立地选自氢、C1~C10烷基、C1~C10烷氧基、C1~C10硅烷基、卤素、氰基和式(2)所示基团中的至少一种,且R1、R2、R3、R4、R5、R6、R7、R3’、R4’、R5’、R6’和R7’不同时为氢;
其中,*为连接位点;L选自单键、取代或未取代的C6~C30亚芳基和取代或未取代的C2~C30亚杂芳基中的一种;Ar选自取代或未取代的C6~C30的芳基,取代或未取代的C2~C30的杂芳基和取代或未取代的C6~C30的芳胺中的一种;
所述取代的C6~C30亚芳基、取代的C2~C30亚杂芳基、取代的C6~C30的芳基、取代的C2~C30的杂芳基和取代的C6~C30的芳胺中的取代基各自独立地选自卤素、C1~C10的烷基、C3~C10的环烷基、C2~C10烯基、C1~C6的烷氧基、C1~C6的硫代烷氧基、C6~C30的芳基和C3~C30的杂芳基中的至少一种。
本公开的含氮杂环化合物中,母核结构含有两个N原子,因而具有缺电特性,并且其具有刚性的平面结构和大的π共轭体系,有利于电子传输,可以作为高迁移率有机半导体材料应用于有机光电领域,能够降低发光器件的驱动电压导致、提高发光效率。该含氮杂环化合物应用范围广,当母核上连接上给电子基团时,其发射峰的峰值在绿光范围内,可以作为绿色磷光主体应用在有机电致发光器件中;当母核上连接拉电子基团时,其电子亲和势增加,生成的化合物更有利于电子的传输,可以作为电子传输材料应用在有机电致发光器件中。
根据本公开,该含氮杂环化合物共平面性较好,为了进一步提高电子传输效率,优选地,R1、R2、R3、R4、R5、R6、R7、R3’、R4’、R5’、R6’和R7’中可以至少一个为式(2)所示基团,进一步地,在本公开的一种优选的具体实施方式中,R1和R2可以均为式(2)所示基团,即该含氮杂环化合物可以具有如下通式(3)所示的结构:
其中,L1、L2可以各自独立地选自单键、取代或未取代的C6~C30亚芳基和取代或未取代的C2~C30亚杂芳基中的一种;Ar1、Ar2可以各自独立地选自取代或未取代的C6~C30的芳基,取代或未取代的C2~C30的杂芳基和取代或未取代的C6~C30的芳胺中的一种。此时,R3、R4、R5、R6、R7、R3’、R4’、R5’、R6’和R7’选择的基团种类可以为氢、C1~C10烷基、C1~C10烷氧基、C1~C10硅烷基、卤素和氰基中的至少一种;进一步优选地,在这一实施方式中,R3、R4、R5、R6、R7、R3’、R4’、R5’、R6’和R7’可以均为氢原子。
根据本公开,取代的C6~C30亚芳基、取代的C2~C30亚杂芳基、取代的C6~C30芳基和取代的C2~C30杂芳基中的取代基可以各自独立地选自卤素、C1~C10的烷基、C3~C10的环烷基、C2~C10烯基、C1~C6的烷氧基、C1~C6的硫代烷氧基、C6~C30的芳基和C3~C30的杂芳基中的至少一种;优选为卤素、C1~C4的烷基、C3~C6的环烷基、C1~C4的烷氧基、苯基和吡啶基中的至少一种;其中,卤素可以为-F、-Cl、-Br、-I中的至少一种,C1~C4的烷基优选为甲基、乙基、正丙基、异丙基、正丁基、异丁基和叔丁基中的至少一种,C1~C4的烷氧基优选为甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基中的至少一种,C3~C6的环烷基优选为环戊基或环己基。
根据本公开,C6~C30的芳基是本领域技术人员所熟知的,即具有6~30个骨架碳原子的芳基,优选具有6~20个骨架碳原子的芳基,例如可以为选自苯基、2-联苯基、3-联苯基、4-联苯基、对-三联苯基-4-基、对-三联苯基-3-基、对-三联苯基-2-基、间-三联苯基-4-基、间-三联苯基-3-基、间-三联苯基-2-基、1-萘基、2-萘基、1-蒽基、2-蒽基、9-蒽基、菲基、茚基、1-芴基、2-芴基、3-芴基、4-芴基、9-芴基、苯并芴基、9,9’-二烷基芴基、9,9’-螺二芴基、茚并芴基、荧蒽基、三亚苯基、1-芘基、2-芘基、4-芘基、苝基、基、三亚苯基、1-并四苯基、2-并四苯基、9-并四苯基和基中的至少一种;优选为苯基、2-联苯基、3-联苯基、4-联苯基、1-萘基、2-萘基、菲基、蒽基、基、荧蒽基、1-芘基、2-芘基、4-芘基、9,9’-二烷基芴基和9,9’-螺二芴基中的至少一种。根据本公开,C6~C30亚芳基是本领域技术人员所熟知的,即具有6~30个骨架碳原子的亚芳基,进一步地,可以为由上述种类的C6~C30的芳基失去一个氢原子形成的亚芳基。
根据本公开,杂芳基是指具有至少一个杂原子且具有一定数目环骨架原子的单环或稠环芳香基团,杂原子可以包含一个或多个选自B、N、O、S、P(=O)、Si和P的杂原子;优选地,杂原子可以包含一个或多个选自O、S和N的杂原子。C2~C30杂芳基具有2~30个骨架碳原子,优选具有4~20个骨架碳原子,例如可以为选自噻吩基、呋喃基、二苯并呋喃基、氮杂二苯并呋喃基、氮杂二苯并噻吩基、二苯并噻吩基、二苯并硒吩基、咔唑基、咔啉基、吡咯基、咪唑基、苯并咪唑基、吲哚基、吡啶基、恶唑基、恶二唑基、苯并恶唑基、三嗪基、嘧啶基、喹唑啉基、喹喔啉基、萘啶基、吩嗪基、菲啰啉基、苯并咪唑基和吲哚并咔唑基中的至少一种;优选为吡啶基、三嗪基、吡啶基、喹啉基、异喹啉基、苯并咪唑基、菲啰啉基、恶唑基、恶二唑基、苯并恶唑基、二苯并呋喃基和二苯并噻吩基中的至少一种。根据本公开,C2~C30亚杂芳基是本领域技术人员所熟知的,即具有2~30个骨架碳原子的亚杂芳基,进一步地,可以为由上述种类的C2~C30亚杂芳基失去一个氢原子形成的亚杂芳基。
根据本公开,C1~C10的烷基是本领域技术人员所熟知的,即具有1~10个碳原子的脂肪族烷基,可以为选自甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基和癸基中的至少一种,其中烷基可以为直连烷基或带有支链的烷基,进一步优选为甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、正己基、正庚基、正辛基、正壬基和正癸基中的至少一种。
根据本公开,C1~C10的烷氧基是本领域技术人员所熟知的,即具有1~10个碳原子的烷氧基,可以为选自甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、叔丁氧基、正戊氧基、正己氧基、正庚氧基、正辛氧基、正壬氧基和正癸氧基中的至少一种,优选为甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、叔丁氧基、正戊氧基和正己氧基中的至少一种。
根据本公开,所述C3~C10的环烷基是本领域技术人员所熟知的,即具有3~10个碳原子的环烷基,优选为环戊基或环己基。
根据本公开,所述C1~C10硅烷基是本领域技术人员所熟知的,即具有1~10个碳原子的烷基取代硅烷或烷氧基取代硅烷,优选为三甲基硅基、三乙基硅基、三甲氧基硅基和三乙氧基硅基中的至少一种。
根据本公开,所述C6~C30的芳胺是本领域技术人员所熟知的,即具有1~10个碳原子的芳香族胺类化合物,优选为二芳胺或三芳胺,进一步优选为二苯胺或三苯胺。
根据本公开,式(1)所示的结构中,Ar优选为取代或未取代的苯基、联苯基、萘基、蒽基、荧蒽基、菲基、芘基、基、二苯并呋喃基、二苯并噻吩基、芴基、螺二芴基、三亚苯基、吡啶基、喹啉基、异喹啉基、苯并咪唑基、嘧啶基、三嗪基、菲啰啉基、恶二唑基和苯并恶唑基中的至少一种;其中,取代的Ar的取代基可以选自甲基、异丙基、环己基、甲氧基、三甲基硅基和叔丁基中的至少一种。
根据本公开,式(1)所示的结构中,当L不是化合键时,L可以选自亚苯基、亚萘基和亚吡啶基中的一种。
根据本公开,式(3)所示的结构中,L1和L2可以相同或不同,优选L1和L2相同,L1和L2可以各自独立地选自单键、亚苯基、亚吡啶基和亚萘基中的至少一种;Ar1和Ar2可以相同或不同,优选二者相同;Ar1和Ar2可以各自独立地选自取代或未取代的苯基、联苯基、萘基、蒽基、荧蒽基、菲基、芘基、基、二苯并呋喃基、二苯并噻吩基、芴基、螺二芴基、三亚苯基、吡啶基、喹啉基、异喹啉基、苯并咪唑基、嘧啶基、三嗪基、菲啰啉基、恶二唑基和苯并恶唑基中的至少一种;其中,取代的Ar1和Ar2的取代基可以各自独立地选自甲基、异丙基、环己基、甲氧基、三甲基硅基和叔丁基中的至少一种。进一步地,在本公开优选的一种具体实施方式中,L1和L2相同,Ar1和Ar2相同,并且R1、R2、R3、R4、R5、R6、R7、R3’、R4’、R5’、R6’和R7’均为氢原子,即优选含氮杂环化合物分子呈对称结构。
根据本公开,式(3)所示的结构中,当L1、L2不是化合键时,L1、L2可以各自独立地选自亚苯基、亚萘基和亚吡啶基中的至少一种。
根据本公开,式(1)或式(3)所示的结构中,R1、R2、R3、R4、R5、R6、R7、R3’、R4’、R5’、R6’和R7’中优选具有1~4个非氢原子的取代基,例如,在本公开的一种具体实施方式中,所述含氮杂环化合物具有4个非氢原子的取代基,R3、R4、R6、R7、R3’、R4’、R6’和R7’均为氢,R1、R2、R5和R5’各自独立地选自C1~C10烷基、C1~C10烷氧基、C1~C10硅烷基、卤素、氰基和式(2)所示基团中的一种;在另一种具体实施方式中,所述含氮杂环化合物具有2个非氢原子的取代基,R3、R4、R5、R6、R7、R3’、R4’、R5’、R6’和R7’均为氢,R1和R2各自独立地选自C1~C10烷基、C1~C10烷氧基、C1~C10硅烷基、卤素、氰基和式(2)所示基团中的至少一种。
根据本公开,所述含氮杂环化合物可以选自以下结构式之一:
本公开第二方面提供上述第一方面的含氮杂环化合物在制备有机电致发光器件中的应用。
根据本公开,所述含氮杂环化合物具有较好的电子传输性能,可以用作所述有机电致发光器件的磷光主体材料和/或电子传输材料。
进一步地,所述含氮杂环化合物的母核上连接有给电子基团时,即R1、R2、R3、R4、R5、R6、R7、R3’、R4’、R5’、R6’和R7’中至少一个为给电子基团,该化合物的发射峰的峰值在绿光范围内,能够作为绿色磷光主体应用在有机电致发光器件中;而当母核上连接拉电子基团时,其电子亲和势增加,生成的化合物更有利于电子的传输,可以作为电子传输材料应用在有机电致发光器件中。所述的拉电子基团可以包括吡啶、嘧啶、三嗪、喹啉、三唑、喹喔啉、喹唑啉、菲咯啉、吲哚中的至少一种。
本公开第三方面提供一种有机电致发光器件,包括基板、阳极层、阴极层、以及介于阳极层与阴极层之间的至少一层有机功能层,所述有机功能层包括空穴注入层、空穴传输层、有机发光层、电子传输层以及电子注入层,所述的空穴注入层、空穴传输层、有机发光层、电子传输层以及电子注入层依次形成在所述的阳极层上,所述的阴极层形成在所述的电子传输层上,所述有机发光层的磷光主体材料和/或电子传输层中含有本公开第一方面所述的含氮杂环化合物,优选含有化合物A1~A70和B1~B32中的至少一种。
本公开的有机电致发光器件基于本公开化合物的优异性能,能够降低器件工作电压,提高发光效率,延长器件寿命。
下面对本公开的含氮杂化合物的合成方法进行简要的说明。
除特别说明外,本公开中所用原料、中间体均为市售商品;本公开中质谱采用ABSCIEX质谱仪(4000QTRAP)测定,核磁采用布鲁克核磁共振仪(400M Hz)测定,元素分析采用vario EL型元素分析仪测定(英国Elementar Analysensysteme GmbH公司制造)。
本公开的含氮杂环化合物可以由以下两条示例性的反应路线合成:
路线1:
路线2:
下面结合合成实施例1-9来具体说明以上两条合成路线。
合成实施例1:化合物A1的合成
N2保护下,向装有机械搅拌,低温温度计的2L三口瓶中加入溴苯(39.25g,0.25mol),四氢呋喃(600mL),开启搅拌,体系溶解,冰乙醇冷浴冷却,液氮降温至-80℃,30min内滴加正丁基锂(2.5N,100mL),滴加过程中控温-80℃左右,滴加完毕后-80℃保温1h,加入化合物M(28.63g,0.1mol),大约20min加完,加毕自然升温,室温搅拌8小时。TLC监控反应完毕
反应完毕,加入约10%的氯化铵水溶液100mL,搅拌30min,向反应体系中补加乙酸乙酯300mL,静置分液,有机相分出,水相用乙酸乙酯洗涤两遍合并有机相用饱和食盐水洗涤一遍。有机相用无水硫酸钠进行干燥,过滤,滤液收干,正己烷打浆直接用于下一步。得到中间体A1-1,棕色粉末40.27g,收率91.1%。
N2保护,向反应瓶中加入乙酸200mL,开启搅拌、加热,反应液升温至60℃左右时加入中间体A1-1(40.27g,0.091mol),KI(75.63g,0.455mol),NaHPO2.H2O(62.58g,0.728mol),回流反应5小时,TLC监控反应完成,停止加热。
约100min冷却至50℃,抽滤,依次用乙酸100mL、去离子水100mL,无水乙醇200mL淋洗并抽干,得到黄色固体。
将得到的黄色固体用氯仿溶解,硅胶拌样,柱层析进行纯化,展开剂石油醚:乙酸乙酯(5:1),得到类白色粉末固体A1,29.9g,收率80.5%。
其中,化合物M参考org.lett.2016,18,6050-6053中的方法制备。
化合物A1核磁数据:1H NMR(500MHz,Chloroform)δ7.56–7.42(m,16H),7.41(s,2H),7.11(s,3H),6.68(s,3H),6.41(s,3H),6.24(s,3H).
化合物A1元素分析数据:C,88.21;H,4.93;N,6.86。
合成实施例2:化合物A14的合成
采用化合物A1的合成方法,不同在于将溴苯替换为等当量的2-溴萘,得到白色粉末A14,31.2g,总收率57.7%。
A14核磁数据:1H NMR(500MHz,Chloroform)δ8.08(d,J=15.0Hz,4H),7.99(s,2H),7.63(s,2H),7.58(s,2H),7.55(s,2H),7.44(s,2H),7.38(s,2H),7.11(s,2H),6.68(s,2H),6.41(s,2H),6.24(s,2H).
A14元素分析数据:C,89.74;H,4.76;N,5.51
合成实施例3:化合物A18的合成
采用化合物A1的合成方法,不同在于将溴苯替换为等当量的3-溴荧蒽,得到白色粉末A18,38.2g,总收率58.2%。
A14核磁数据:1H NMR(500MHz,Chloroform)δ8.42(s,4H),8.10(s,4H),7.76(s,2H),7.67(s,4H),7.46(d,J=20.0Hz,4H),7.37(s,2H),7.11(s,2H),6.68(s,2H),6.41(s,2H),6.24(s,2H).
A14元素分析数据:C,91.44;H,4.30;N,4.27
合成实施例4:化合物A21的合成
采用化合物A1的合成方法,不同在于将溴苯替换为等当量的2-溴二苯并呋喃,得到白色粉末A21,25.6g,总收率43.5%。
A21核磁数据:1H NMR(500MHz,Chloroform)δ8.45(s,2H),7.98(s,2H),7.66(d,J=30.0Hz,4H),7.54(s,2H),7.44(s,2H),7.39(s,2H),7.31(s,2H),7.11(s,2H),6.68(s,2H),6.41(s,2H),6.24(s,2H).
A21元素分析数据:C,85.70;H,4.11;N,4.76;O,5.44
合成实施例5:化合物A46的合成
N2保护下,向装有机械搅拌,低温温度计的2L三口瓶中加入3-溴二苯并呋喃(24.7g,0.1mol),四氢呋喃(300mL),开启搅拌,体系溶解,冰乙醇冷浴冷却,液氮降温至-80℃,30min内滴加正丁基锂(2.5M,40mL),滴加过程中控温-80℃左右,滴加完毕后-80℃保温1h,加入化合物M(28.63g,0.1mol),大约20min加完,加毕自然升温,室温搅拌8小时。TLC监控反应完毕
反应完毕,加入约10%的氯化铵水溶液100mL,搅拌30min,向反应体系中补加乙酸乙酯300mL,静置分液,有机相分出,水相用乙酸乙酯洗涤两遍合并有机相用饱和食盐水洗涤一遍。有机相用无水硫酸钠进行干燥,过滤,滤液收干,正己烷打浆直接用于下一步。得到中间体A46-1,黄色粉末41.6g,收率91.6%。
N2保护下,向装有机械搅拌,低温温度计的2L三口瓶中加入溴苯(28.9g,0.184mol),四氢呋喃(300mL),开启搅拌,体系溶解,冰乙醇冷浴冷却,液氮降温至-80℃,30min内滴加正丁基锂(2.5N,73.6mL),滴加过程中控温-80℃左右,滴加完毕后-80℃保温1h,加入中间体A46-1(41.6g,0.092mol),大约20min加完,加完后自然升温,室温搅拌8小时。TLC监控反应完毕。
反应完毕,加入约10%的氯化铵水溶液100mL,搅拌30min,向反应体系中补加乙酸乙酯300mL,静置分液,有机相分出,水相用乙酸乙酯洗涤两遍合并有机相用饱和食盐水洗涤一遍。有机相用无水硫酸钠进行干燥,过滤,滤液收干,正己烷打浆直接用于下一步。得到中间体A46-2,黄色粉末29.8g,收率60.8%。
N2保护,向反应瓶中加入乙酸200mL,开启搅拌、加热,反应液升温至60℃左右时加入中间体A46-2(29.8g,0.056mol),KI(46.5g,0.28mol),NaHPO2.H2O(38.53g,0.448mol),回流反应5小时,TLC监控反应完成,停止加热。
约100min冷却至50℃,抽滤,依次用乙酸100mL、去离子水100mL,无水乙醇200mL淋洗并抽干,得到黄色固体。
将得到的黄色固体用氯仿溶解,硅胶拌样,柱层析进行纯化,展开剂石油醚:乙酸乙酯(5:1),得到类白色粉末固体中间体A46,22.8g,收率81.7%。
A46核磁数据:1H NMR(500MHz,Chloroform)δ8.18(s,1H),7.98(s,1H),7.78(s,1H),7.57(s,1H),7.54(s,1H),7.51(s,2H),7.45(d,J=10.0Hz,3H),7.41(s,2H),7.39(s,1H),7.31(s,1H),7.11(s,2H),6.68(s,2H),6.41(s,2H),6.24(s,2H).
A46元素分析数据:C,86.72;H,4.45;N,5.62;O,3.21
合成实施例6:化合物A50的合成
采用化合物A46的合成方法,不同在于将3-溴二苯并呋喃替换为等当量的2-溴螺二芴,得到类白色粉末A46,15.2g。
A50核磁数据:1H NMR(500MHz,Chloroform)δ8.20(s,61H),8.09(s,65H),8.19–7.87(m,251H),8.19–7.53(m,513H),7.53(d,J=0.6Hz,5H),7.51(s,114H),7.49–7.39(m,298H),7.34(s,63H),7.28(t,J=5.0Hz,34H),7.30–6.97(m,439H),6.68(s,120H),6.41(s,101H),6.24(s,123H).
A50元素分析数据:C,90.99;H,4.68;N,4.33
合成实施例7:化合物A55合成
采用化合物A46的合成方法,不同在于将3-溴二苯并呋喃替换为等当量的2-溴萘,将溴苯替换为对应量的1-溴萘,反应完成后得到类白色粉末A55,16.3g。
A55核磁数据:1H NMR(500MHz,Chloroform)δ8.95(s,1H),8.50(s,1H),8.08(d,J=15.0Hz,2H),7.99(s,1H),7.77(dd,J=67.5,62.5Hz,4H),7.63(s,1H),7.63(s,1H),7.57(d,J=15.0Hz,2H),7.44(s,2H),7.39(d,J=10.0Hz,2H),7.34(s,1H),7.11(s,2H),6.68(s,2H),6.41(s,2H),6.24(s,2H).
A55元素分析数据:C,89.74;H,4.76;N,5.51
合成实施例8:化合物A69的合成
采用化合物A46的合成方法,不同在于将3-溴二苯并呋喃替换为等当量的2-(4-溴苯基)-9,9-二甲基芴,将溴苯替换为对应量的3-溴荧蒽,反应完成后得到类白色粉末A69,16.8g。
A69核磁数据:1H NMR(500MHz,Chloroform)δ8.42(s,2H),8.09(t,J=3.0Hz,4H),7.90(s,1H),7.77(d,J=10.0Hz,2H),7.67(s,2H),7.61(s,1H),7.46(d,J=20.0Hz,2H),7.43(d,J=3.1Hz,1H),7.36(d,J=13.6Hz,2H),7.25(d,J=3.6Hz,5H),7.11(s,2H),6.68(s,2H),6.41(s,2H),6.24(s,2H),1.69(s,6H).
A69元素分析数据:C,91.13;H,5.01;N,3.86
合成实施例9:化合物B10的合成
采用化合物A1的合成方法,不同在于将溴苯替换为等当量的6-溴喹啉,得到白色粉末B10,28.2g,总收率55.2%。
B10核磁数据:1H NMR(500MHz,Chloroform)δ8.91(s,1H),8.38(d,J=3.2Hz,2H),8.08(s,1H),7.75(s,1H),7.42(d,J=15.0Hz,2H),7.11(s,1H),6.68(s,1H),6.41(s,1H),6.24(s,1H).
B10元素分析数据:C,69.89;H,3.58;B,17.47;N,9.06
器件实施例
本公开有机电致发光器件的结构为: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。
基板可以使用传统有机发光器件中的基板,例如:玻璃、聚合物材料以及带有TFT元器件的玻璃和聚合物材料等,优选使用玻璃基板。
阳极层材料可以采用铟锡氧(ITO)、铟锌氧(IZO)、二氧化锡(SnO2)、氧化锌(ZnO)等透明导电材料,也可以是银及其合金、铝及其合金等金属材料,也可以是PEDOT等有机导电材料,及上述材料的多层结构。阴极层材料可以为镁银混合物、LiF/Al、ITO等金属、金属混合物、氧化物。
器件中还可以包括位于空穴传输层与阳极之间的空穴注入层,空穴注入层材料和空穴传输层材料可以各自独立地选自以下化学物HT-1~HT-31中的至少一种:
根据本公开,有机电致发光器件的有机发光层可以为单发光层也可以是多发光层结构;发光颜色不限,可以为如红、黄、蓝、绿等,有机发光层可以包括主体材料和掺杂染料,其中,磷光主体材料包括可以包括以下化合物GPH-1~GPH-80中的至少一种:
磷光掺杂剂可以包括以下化合物GPD-1~GPD-57中的至少一种:
电子传输材料可以包括以下化合物ET-1~ET-59中的至少一种:
器件中还可以包括位于电子传输层与阴极之间的电子注入层,电子注入层材料包括但不限于以下罗列的一种或多种的组合。
LiQ,LiF,NaCl,CsF,Li2O,Cs2CO3,BaO,Na,Li,Ca。
阴极为镁银混合物、LiF/Al、ITO等金属、金属混合物、氧化物。
器件对比例1:以化合物GPH-77作为发光层主体材料,以化合物ET-35作为电子传输层材料。器件的制作过程如下:
将表面涂覆了ITO透明导电薄膜的玻璃基板在清洗液中超声清洗,在去离子水中超声处理,在丙酮∶乙醇混合溶剂(体积比1∶1)混合溶液中超声除油,在洁净环境下烘烤至完全去除水分,用紫外灯进行刻蚀和臭氧处理,并用低能阳离子束轰击表面;
把上述带有阳极的玻璃基片置于真空腔内,抽真空至1×10-5~9×10-3Pa,在上述阳极层膜上真空蒸镀HT-9作为空穴注入层,蒸镀速率为0.1nm/s,蒸镀总膜厚为40nm;然后蒸镀空穴传输层HT-7,蒸镀速率为0.1nm/s,蒸镀膜厚为10nm;
在空穴传输层之上真空蒸镀EML作为器件的发光层,EML包括主体材料和染料材料,利用多源共蒸的方法,将作为发光层主体的GPH-77放置在真空气相沉积设备的小室中,将作为掺杂剂的GPD-28放置在真空气相沉积设备的另一室中,调节主体材料GPH-77蒸镀速率为0.1nm/s,GPD-28的浓度为10%,蒸镀总膜厚为20nm;
在发光层上真空蒸镀ET-35形成膜厚为50nm的电子传输层,其蒸镀速率为0.1nm/s;
在电子传输层上依次真空蒸镀厚度为1nm的LiF作为电子注入层,厚度为150nm的Al层作为器件的阴极,得到本实施例的有机电致发光器件。
器件实施例1-8:以本公开的化合物作为磷光主体材料。
采用器件对比例1的方法,不同在于将主体材料化合物GPH-77分别替换为A10,A14,A18,A21,A46,A50,A55和A69作为磷光主体材料,得到本实施例的有机电致发光器件。
器件实施例9-17:以本公开的化合物作为电子传输材料。
采用器件对比例1的方法,不同在于将电子传输材料ET-35分别替换为化合物B5,B10,B11,B16,B22,B23,B26和B29,得到本实施例的有机电致发光器件。
器件实施例18:分别以本公开的化合物作为磷光主体材料和电子传输材料。
采用器件对比例1的方法,不同在于将主体材料化合物GPH-77替换为化合物A55,并且将电子传输材料ET-35替换为化合物B11,得到本实施例的有机电致发光器件。
对由上述过程制备的有机电致发光器件进行如下性能测定:
在同样亮度下,使用数字源表及亮度计测定器件实施例1~18以及器件对比例1中制备得到的有机电致发光器件的驱动电压和电流效率。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器件的亮度达到2000cd/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;测试结果分别列于表1中。
表1
以上结果表明,本发明的新型有机材料用于有机电致发光器件,可以有效的降低起亮电压和提高电流效率,是性能良好的磷光主体材料和电子传输材料。
以上详细描述了本公开的优选实施方式,但是,本公开并不限于上述实施方式中的具体细节,在本公开的技术构思范围内,可以对本公开的技术方案进行多种简单变型,这些简单变型均属于本公开的保护范围。
另外需要说明的是,在上述具体实施方式中所描述的各个具体技术特征,在不矛盾的情况下,可以通过任何合适的方式进行组合。为了避免不必要的重复,本公开对各种可能的组合方式不再另行说明。
此外,本公开的各种不同的实施方式之间也可以进行任意组合,只要其不违背本公开的思想,其同样应当视为本公开所公开的内容。
Claims (9)
1.一种含氮杂环化合物,其特征在于,该含氮杂环化合物具有如下通式(1)所示的结构:
其中,R3、R4、R5、R6、R7、R3’、R4’、R5’、R6’和R7’各自独立地选自氢或苯基,R1和R2各自独立地为式(2)所示基团;
其中,*为连接位点;L选自单键、亚苯基、亚萘基和亚吡啶基中的一种;Ar选自取代或未取代的苯基、联苯基、萘基、蒽基、荧蒽基、菲基、芘基、基、二苯并呋喃基、二苯并噻吩基、芴基、螺二芴基、三亚苯基、吡啶基、喹啉基、异喹啉基、苯并咪唑基、嘧啶基、三嗪基、菲啰啉基、恶二唑基和苯并恶唑基中的至少一种;
其中,Ar的取代基各自独立地选自苯基、甲基、异丙基、环己基、甲氧基、三甲基硅和叔丁基中的至少一种。
3.根据权利要求1或2所述的含氮杂环化合物,其特征在于,R3、R4、R5、R6、R7、R3’、R4’、R5’、R6’和R7’均为氢。
4.根据权利要求2所述的含氮杂环化合物,其特征在于,Ar1和Ar2相同,且L1和L2相同。
5.根据权利要求4所述的含氮杂环化合物,其特征在于,R3、R4、R5、R6、R7、R3’、R4’、R5’、R6’和R7’均为氢。
7.权利要求1-6中任意一项所述的含氮杂环化合物在制备有机电致发光器件中的应用。
8.根据权利要求7所述的应用,其特征在于,所述含氮杂环化合物用作所述有机电致发光器件的磷光主体材料和/或电子传输材料。
9.一种有机电致发光器件,包括基板、阳极层、阴极层、以及介于阳极层与阴极层之间的至少一层有机功能层,所述有机功能层包括空穴注入层、空穴传输层、有机发光层、电子传输层以及电子注入层,其特征在于,所述有机发光层的磷光主体材料和/或电子传输层含有权利要求1-6中任一项所述的含氮杂环化合物。
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