CN114716467B - 含硼氮的杂环化合物及其在有机电致发光器件中的应用 - Google Patents
含硼氮的杂环化合物及其在有机电致发光器件中的应用 Download PDFInfo
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- CN114716467B CN114716467B CN202210539293.5A CN202210539293A CN114716467B CN 114716467 B CN114716467 B CN 114716467B CN 202210539293 A CN202210539293 A CN 202210539293A CN 114716467 B CN114716467 B CN 114716467B
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- boron
- containing heterocyclic
- nitrogen
- compound
- organic electroluminescent
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 32
- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 239000000463 material Substances 0.000 claims abstract description 35
- 239000011368 organic material Substances 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 2
- 230000003111 delayed effect Effects 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 39
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 abstract description 8
- 229910052805 deuterium Inorganic materials 0.000 abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 8
- 239000001257 hydrogen Substances 0.000 abstract description 8
- 238000004020 luminiscence type Methods 0.000 abstract description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 7
- 229910052731 fluorine Inorganic materials 0.000 abstract description 7
- 239000011737 fluorine Substances 0.000 abstract description 7
- 150000002431 hydrogen Chemical class 0.000 abstract description 7
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 5
- 125000005549 heteroarylene group Chemical group 0.000 abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 abstract description 5
- 125000000732 arylene group Chemical group 0.000 abstract description 4
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 68
- 239000010410 layer Substances 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 239000000543 intermediate Substances 0.000 description 23
- 230000015572 biosynthetic process Effects 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 16
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 12
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- 238000001816 cooling Methods 0.000 description 10
- 239000012299 nitrogen atmosphere Substances 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 239000012295 chemical reaction liquid Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- -1 dibenzofuranyl Chemical group 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- 125000006749 (C6-C60) aryl group Chemical group 0.000 description 1
- 125000006761 (C6-C60) arylene group Chemical group 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
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Abstract
本发明公开了含硼氮的杂环化合物及其在有机电致发光器件中的应用,该化合物具有如式(1)所示的结构,其中A1‑N‑A2‑B形成的环与A2‑N‑A3‑B形成的环中至少一个为七元环;A1、A2和A3独立选自取代或未取代的C6–C30亚芳基或C5–C30亚杂芳基;Y1和Y2各自独立选自氢、氘、氟、‑CF3、‑CN、‑NO2、取代或未取代的C6–C30芳基、取代或未取代的C5–C30杂芳基、C(=O)RaRb或S(=O)2RaRb等。本发明中含硼氮的杂环化合物刚性强且分子结构稳定,可作为有机电致发光器件的磷光发光主体材料和热延迟荧光发光材料,同时适用于在绿色、蓝色和蓝绿色发光,发光效率和使用寿命均好。
Description
技术领域
本发明属于有机电致发光材料领域,具体涉及含硼氮的杂环化合物及其在有机电致发光器件中的应用。
背景技术
有机电致发光二极管(简称为OLED)因其具有自发光、固态、可弯折、高效率等特点,广泛应用于各类显示器件中,随着OLED发光材料的不断发展,市场上已经出现很多性能优异的电致发光材料,但在发光效率上仍有改进空间,其中磷光作为具有高效率、高亮度的发光机制,磷光主体材料作为能量传递的重要角色,在发光效率和使用寿命方面都有重要作用。磷光主体材料需要同时传输空穴和电子,保持电子和空穴的平衡,因此其分子结构上需要加入空穴传输单元和电子传输单元,一般情况两类不同的单元都是独立单元并相互连接,容易造成分子极性大和激发时稳定性差的问题。
相较于普通的荧光材料只有25%的发光效率,磷光发光材料理论上具有100%的内量子发光效率,因此其仍是当前主流的高效率发光材料。但是,磷光发光材料需要用到重金属,从成本和对环境污染等方面仍有待改善。热延迟荧光发光材料具有单线态、三线态的能级差小、三线态能量能够上转移至单线态形成荧光发光,理论上也能达到100%的发光效率,是一类可替代磷光发光体材料的选择之一。
发明内容
本发明提供一种含硼氮的杂环化合物,其具有如式(1)所示的结构:
式(1)中,A1-N-A2-B形成的环与A2-N-A3-B形成的环中至少一个为七元环;
A1、A2和A3各自独立选自取代或未取代的C6–C30亚芳基、取代或未取代的C5–C30亚杂芳基,且杂原子选自O、N、S、P、Si、Se或B;
Y1和Y2各自独立选自氢、氘、氟、-CF3、-CN、-NO2、取代或未取代的C6–C30芳基、取代或未取代的C5–C30杂芳基、C(=O)RaRb、N(RaRbRc)、Si(RaRbRcRd)、P(=O)(RaRbRc)或S(=O)2RaRb,其中Ra与式(1)中的氮原子相连,选自取代或未取代的C6–C60亚芳基、取代或未取代的C5–C30亚杂芳基,Rb、Rc和Rd各自独立选自为氢、氘、取代或未取代的C6–C60芳基、取代或未取代的C5–C30杂芳基、取代或未取代的C6–C30胺基、或者Ra、Rb、Rc和Rd中任意两个连接成环,所述取代或未取代的C5–C30杂芳基中杂原子选自O、N、S、P、Si、Se或B。
作为优选,式(1)中,A1、A2和A3至少一个为如式(2)所示的基团结构:
式(2)中,Re–Rj各自独立选自取代或未取代的C6–C30亚芳基、取代或未取代的C5–C30亚杂芳基、或者任意两个相邻基团连接成稠基环、烷基环或稠基并烷基环中的一种;
#为与B原子和N原子的连接位置。
作为优选,式(1)所示的含硼氮的杂环化合物选自如式1-1、1-2、1-3和1-4所示的任一结构:
式1-1至1-4中,Y1和Y2如上所述;
R1–R15各自独立选自氢、氘、氟、-CF3、-CN、-NO2、取代或未取代的C1-C10直链或支链烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C10杂烷基、取代或未取代的C6-C30芳基、取代或未取代的C5-C30的杂芳基、或者其中两个及以上相邻基团彼此连接成环。
作为优选,在式(1)、(2)、1-1、1-2、1-3和1-4中,“取代或未取代的”的“取代的”表示被独立选自氢、氘、氟、-CF3、-CN、-NO2、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、环丁基、环戊基、环己基、苯基、萘基、联苯基、二苯并呋喃基、二苯并噻吩基、咔唑基、中的一个或多个取代基所取代,其中取代基彼此相同或不同。
作为优选,在式(1)中,Y1和Y2各自独立选自氢、氘、氟、-CF3、-CN、-NO2和以下基团中的一种或两种以上组合:
其中,Ar选自取代或未取代的C6–C30亚芳基、取代或未取代的C5–C30亚杂芳基;
Aa和Ab各自独立选自氢、氘、氟、-CF3、-CN、-NO2、取代或未取代的C6-C20芳基、取代或未取代的C5-C20的杂芳基;
X选自O或S;
X1–X7各自独立选自O、S或CRkRl,且Rk和Rl各自独立选自氢、氘、氟、-CF3、-CN、-NO2、C1-C10直链或支链烷基、取代或未取代的C3-C20环烷基;
上述取代基的任意位置含有一个连接位点。
作为优选,所述含硼氮的杂环化合物选自如下所示的化学结构中的一种或多种:
本发明还提供上述含硼氮的杂环化合物在有机电致发光器件中的应用,例如作为有机电致发光器件的磷光发光主体材料或热延迟荧光发光材料。
本发明还提供一种有机材料,其包含上述任一所述含硼氮的杂环化合物,可以作为有机电致发光器件的磷光发光主体材料或者热延迟荧光发光材料。
本发明还提供一种有机电致发光器件,包括基板、第一电极、包含发光层和第二电极元件,所述含硼氮的杂环化合物或者所述有机材料作为所述发光层的磷光发光主体材料或热延迟荧光发光材料。
本发明还提供一种显示或照明装置,其特征在于,包括权所述有机电致发光器件。
与现有技术相比,本发明中含硼氮的杂环化合物是一类刚性强和分子结构稳定的化合物,由于氮原子的供电子基团和硼原子的吸电子基团相连接,最高未占据轨道和最低已占据轨道之间产生非常好的分离,具有非常小的单线态和三线态能量差,作为有机电致发光器件的热延迟荧光发光材料综合性能优异。此外,尽管氮硼杂环化合物已证明在蓝光热延迟荧光发光性能好,而在绿光热延迟荧光发光方面则鲜有相关报道,本发明中含硼氮的杂环化合物可同时适用于在绿色、蓝色和蓝绿色发光,且该化合物的三线态能够应用于红光的发光主体材料,发光效率和使用寿命均好,应用范围大,市场前景好。
附图说明
图1是实施例中底部发光有机电致发光器件的结构示意图。
图2是实施例中顶部发光有机电致发光器件的结构示意图。
附图标记如下:101基底层,102第一电极(阳极),103空穴注入层,104第一层空穴传输层,105第二层空穴传输层,106有机发光层,107空穴阻挡层,108电子传输层,109第二电极(阴极),110覆盖层。
具体实施方式
下面结合合成实施例来具体说明本发明的有机化合物的合成方法,本发明中未提及合成方法的化合物均通过商业途径获得。
以下合成实施例中提供化合物A–D系列的合成,具体如下:
(1)A系列的化合物合成:
(1-1)中间体A-3的合成:
在三口烧瓶中,加入A-1(1当量),A-2(1当量,),三(二亚苄基丙酮)二钯(Pd2(dba)3,0.02当量),三叔丁基膦(t-Bu3P,0.1当量),叔丁醇钠(NaOBu-t,3当量),在氮气氛围下在甲苯溶剂(toluene)中搅拌,反应液升温至110℃,搅拌反应3小时。反应液冷却至室温,用甲苯和水萃取,甲苯相蒸干,固体用甲苯-石油醚体系进行柱色谱分离纯化,然后真空干燥,进行重结晶纯化,得到化合物A-3。
(1-2)中间体A-5的合成:
在三口烧瓶中,加入A-3(1当量),A-4(1当量,),三(二亚苄基丙酮)二钯(Pd2(dba)3,0.02当量),三叔丁基膦(t-Bu3P,0.1当量),叔丁醇钠(NaOBu-t,3当量),在氮气氛围下在甲苯溶剂(toluene)中搅拌,反应液升温至110℃,搅拌反应3小时。反应液冷却至室温,用甲苯和水萃取,甲苯相蒸干,固体用甲苯-石油醚体系进行柱色谱分离纯化,溶液旋干进行重结晶纯化,得到化合物A-5。
(1-3)中间体A-7的合成:
在三口烧瓶中,加入A-5(1当量),A-6(1当量,),三(二亚苄基丙酮)二钯(Pd2(dba)3,0.02当量),三叔丁基膦(t-Bu3P,0.1当量),叔丁醇钠(NaOBu-t,3当量),在氮气氛围下在甲苯溶剂(toluene)中搅拌,反应液升温至110℃,搅拌反应3小时。反应液冷却至室温,用甲苯和水萃取,甲苯相蒸干,固体用甲苯-石油醚体系进行柱色谱分离纯化,溶液旋干进行重结晶纯化,得到化合物A-7。
(1-4)化合物A8的合成:
在氮气气氛下,将溶解在叔丁基苯中的中间体A-7(1当量)加入至圆底烧瓶中,并将温度升高至90℃。将1.7M叔丁基锂(t-BuLi,1.2当量)滴加至该烧瓶,并将该溶液搅拌3小时。在将温度冷却至零度,将三溴化硼(BBr3,1.2当量)缓慢滴加至该烧瓶,滴加完毕后将该溶液在室温下搅拌12小时。用饱含氯化铵溶液淬灭剩余的叔丁基锂,用有机层用氯仿进行萃取,并用水进行洗涤。有机层利用无水MgSO4除去水分,然后在减压下进行浓缩从而得到中间体A-8。
(1-5)中间体A的合成:
在氮气气氛下,将化合物A-8(1当量)和三氟甲磺酸三甲基硅酯(TMS-OTF,0.05当量)溶解在甲苯中,温度升温至80度,搅拌10小时。反应结束后,甲苯-石油醚体系进行柱色谱分离纯化2次,然后用重结晶纯化2次,获得固体化合物A。
(2)B系列的化合物合成:
(2-1)中间体B-3的合成:
在三口烧瓶中,加入B-1(1当量),B-2(1当量,),三(二亚苄基丙酮)二钯(Pd2(dba)3,0.02当量),三叔丁基膦(t-Bu3P,0.1当量),叔丁醇钠(NaOBu-t,3当量),在氮气氛围下在甲苯溶剂(toluene)中搅拌,反应液升温至110℃,搅拌反应3小时。反应液冷却至室温,用甲苯和水萃取,甲苯相蒸干,固体用甲苯-石油醚体系进行柱色谱分离纯化,然后真空干燥,进行重结晶纯化,得到化合物B-3。
(2-2)中间体B-5的合成:
在三口烧瓶中,加入B-3(1当量),B-4(1当量,),三(二亚苄基丙酮)二钯(Pd2(dba)3,0.02当量),三叔丁基膦(t-Bu3P,0.1当量),叔丁醇钠(NaOBu-t,3当量),在氮气氛围下在甲苯溶剂(toluene)中搅拌,反应液升温至110℃,搅拌反应3小时。反应液冷却至室温,用甲苯和水萃取,甲苯相蒸干,固体用甲苯-石油醚体系进行柱色谱分离纯化,溶液旋干进行重结晶纯化,得到化合物B-5。
(2-3)中间体B-7的合成:
在三口烧瓶中,加入B-5(1当量),B-6(1当量,),三(二亚苄基丙酮)二钯(Pd2(dba)3,0.02当量),三叔丁基膦(t-Bu3P,0.1当量),叔丁醇钠(NaOBu-t,3当量),在氮气氛围下在甲苯溶剂(toluene)中搅拌,反应液升温至110℃,搅拌反应3小时。反应液冷却至室温,用甲苯和水萃取,甲苯相蒸干,固体用甲苯-石油醚体系进行柱色谱分离纯化,溶液旋干进行重结晶纯化,得到化合物B-7。
(2-4)中间体B-8的合成:
在氮气气氛下,将溶解在叔丁基苯中的中间体B-7(1当量)加入至圆底烧瓶中,并将温度升高至90℃。将1.7M叔丁基锂(t-BuLi,1.2当量)滴加至该烧瓶,并将该溶液搅拌3小时。在将温度冷却至零度,将三溴化硼(BBr3,1.2当量)缓慢滴加至该烧瓶,滴加完毕后将该溶液在室温下搅拌12小时。用饱含氯化铵溶液淬灭剩余的叔丁基锂,用有机层用氯仿进行萃取,并用水进行洗涤。有机层利用无水MgSO4除去水分,然后在减压下进行浓缩从而得到中间体B-8。
(2-5)化合物B的合成:
在氮气气氛下,将化合物B-8(1当量)和三氟甲磺酸三甲基硅酯(TMS-OTF,0.05当量)溶解在甲苯中,温度升温至80度,搅拌10小时。反应结束后,甲苯-石油醚体系进行柱色谱分离纯化2次,然后用重结晶纯化2次,获得固体化合物B。
(3)化合物C的合成:
(3-1)化合物C5与化合物A5合成方法相同。
(3-2)中间体C-7的合成:
在三口烧瓶中,加入C-5(1当量),C-6(1当量,),三(二亚苄基丙酮)二钯(Pd2(dba)3,0.02当量),三叔丁基膦(t-Bu3P,0.1当量),叔丁醇钠(NaOBu-t,3当量),在氮气氛围下在甲苯溶剂(toluene)中搅拌,反应液升温至110℃,搅拌反应3小时。反应液冷却至室温,用甲苯和水萃取,甲苯相蒸干,固体用甲苯-石油醚体系进行柱色谱分离纯化,溶液旋干进行重结晶纯化,得到化合物C-7。
(3-3)化合物C-8的合成:
在氮气气氛下,将溶解在叔丁基苯中的中间体C-7(1当量)加入至圆底烧瓶中,并将温度升高至90℃。将1.7M叔丁基锂(t-BuLi,1.2当量)滴加至该烧瓶,并将该溶液搅拌3小时。在将温度冷却至零度,将三溴化硼(BBr3,1.2当量)缓慢滴加至该烧瓶,滴加完毕后将该溶液在室温下搅拌12小时。用饱含氯化铵溶液淬灭剩余的叔丁基锂,用有机层用氯仿进行萃取,并用水进行洗涤。有机层利用无水MgSO4除去水分,然后在减压下进行浓缩从而得到中间体C-8。
(3-3)化合物C的合成:
在氮气气氛下,将化合物C-8(1当量)和三氟甲磺酸三甲基硅酯(TMS-OTF,0.05当量)溶解在甲苯中,温度升温至80度,搅拌10小时。反应结束后,甲苯-石油醚体系进行柱色谱分离纯化2次,然后用重结晶纯化2次,获得固体化合物C。
(4)化合物D的合成:
(4-1)化合物D5与化合物B5合成方法相同。
(4-2)中间体D-7的合成:
在三口烧瓶中,加入D-5(1当量),C-6(1当量,),三(二亚苄基丙酮)二钯(Pd2(dba)3,0.02当量),三叔丁基膦(t-Bu3P,0.1当量),叔丁醇钠(NaOBu-t,3当量),在氮气氛围下在甲苯溶剂(toluene)中搅拌,反应液升温至110℃,搅拌反应3小时。反应液冷却至室温,用甲苯和水萃取,甲苯相蒸干,固体用甲苯-石油醚体系进行柱色谱分离纯化,溶液旋干进行重结晶纯化,得到化合物D-7。
(4-3)中间体D-8的合成:
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在氮气气氛下,将溶解在叔丁基苯中的中间体D-7(1当量)加入至圆底烧瓶中,并将温度升高至90℃。将1.7M叔丁基锂(t-BuLi,1.2当量)滴加至该烧瓶,并将该溶液搅拌3小时。在将温度冷却至零度,将三溴化硼(BBr3,1.2当量)缓慢滴加至该烧瓶,滴加完毕后将该溶液在室温下搅拌12小时。用饱含氯化铵溶液淬灭剩余的叔丁基锂,用有机层用氯仿进行萃取,并用水进行洗涤。有机层利用无水MgSO4除去水分,然后在减压下进行浓缩从而得到中间体D-8。
(4-4)化合物D的合成:
在氮气气氛下,将化合物D-8(1当量)和三氟甲磺酸三甲基硅酯(TMS-OTF,0.05当量)溶解在甲苯中,温度升温至80度,搅拌10小时。反应结束后,甲苯-石油醚体系进行柱色谱分离纯化2次,然后用重结晶纯化2次,获得固体化合物D。
按照上述通用的合成方法示例性地合成本发明的以下含硼氮的杂环化合物,具体如下:
第一步、合成如下中间体,其性能如表1所示:
表1
第二步、合成如下中间体,其性能如表2所示:
表2
第三步、合成如下中间体,其性能如表3所示:
表3
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第四步、合成如下中间体,其性能如表4所示:
表4
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第五步、通过上述步骤一至四合成本发明的含硼氮的杂环化合物A3、A20、A46、A68、B12、B27、B47、B59、C11、C31、C61、D21、D42和D71,其性能如表5所示:
表5
/>
以下器件实施例中制备的器件采用本发明中含硼氮的杂环化合物均经过升华提纯,且纯度均为99.9%以上,用于有机电致发光器件中红光的发光层主体材料或者绿光发光层的发光体材料。单色器件结构采用如图1或2所示的结构,可在顶发光、底发光或者两层及以上的发光层器件中使用。
器件实施例1
本器件实施例中以含硼氮的杂环化合物A3作为红光发光层的主体材料,以如图1所示的底发光结构制作器件为例,制备工艺为:
在玻璃材质的基底101上,形成透明阳极ITO膜层,膜厚150nm,得到第一电极102作为阳极,之后蒸镀与空穴传输材料/>的混合材料作为空穴注入层103,混合比例为3:97(质量比),之后蒸镀100nm厚度的/>得到第一层空穴传输层104,然后蒸镀100nm厚度的化合物/>得到第二层空穴传输层105,然后以95:5的蒸镀速率蒸镀本发明含硼氮的杂环化合物A3/>与40nm,制作红光发光单元106,然后蒸镀10nm/>形成空穴阻挡层107,然后蒸镀/>与/>混合比例为4:6(质量比)形成厚度30nm的电子传输层108,之后形成厚度100nm的镁银(质量比1:9),作为第二电极109。
器件实施例2–20分别用含硼氮的杂环化合物A16、A20、A36、A68、B12、B19、B27、B35、B47、B56、C3、C11、C22、C31、D6、D21、D42、D52、D71以及对比例1和2分别采用化合物M1和M2/>替代器件实施例1中的含硼氮的杂环A3作为发光层106的主体材料来制备器件。
上述各器件均采用keithley电源和MS-75光谱辐射计的组合测试设备进行性能测试,其中电压采用10mA/cm2时的电压,效率采用10mA/cm2时的电流效率表示(单位为Cd/A),寿命为在10mA/cm2电流时亮度衰减为初始亮度的95%所需要的时间,结果如表6所示。
表6
/>
器件实施例21
本器件实施例中以含硼氮的杂环化合物A46作为绿光或蓝绿光发光层的发光体材料,以如图1所示的底发光结构制作器件为例,制备工艺为:
在玻璃材质的基底101上,形成透明阳极ITO膜层,膜厚150nm,得到第一电极102作为阳极,之后蒸镀与空穴传输材料/>的混合材料作为空穴注入层103,混合比例为3:97(质量比),之后蒸镀100nm厚度的化合物得到第一层空穴传输层104,然后蒸镀40nm厚度化合物得到第二层空穴传输层105,然后以95:5的蒸镀速率蒸镀化合物与本发明含硼氮的杂环化合物A46/>20nm,制作绿光发光单元106,然后蒸镀10nm/>形成空穴阻挡层107,然后蒸镀/>与混合比例为4:6(质量比)形成厚度30nm的电子传输层108,之后形成厚度100nm的镁银(质量比1:9),作为第二电极109。
器件实施例22–27分别用化合物A60、B2、B59、C45、C61、D27以及对比例3采用化合物M3替代器件实施例21中含硼氮的杂环化合物A46作为发光层106的发光体材料来制备器件。
上述各器件均采用keithley电源和MS-75光谱辐射计的组合测试设备进行性能测试,其中器件实施例的电压相对值为:在电流为10mA/cm2时,器件实施例的电压与器件对比例3的电压比值;器件实施例的EQE(EQE指器件的外量子效率)相对值为:在电流为10mA/cm2时,器件实施例的EQE与器件对比例3的EQE的比值;器件实施例的95%寿命相对值为:在10mA/cm2电流时,器件实施例亮度衰减为初始亮度的95%所需要的时间,与器件对比例3所需要的时间的比值,结果如表7所示。
表7
可见,本发明中含硼氮的杂环化合物作为有机电致发光器件的热延迟荧光发光材料可应用在绿色、蓝色或蓝绿色等多种单色器件中发光,降低驱动电压的同时提高器件的发光效率和使用寿命。
以上所述,仅为本发明较佳的具体实施方式,但本发明的保护范围并不局限于此,任何熟悉本技术领域的技术人员在本发明揭露的技术范围内,根据本发明的技术方案及其发明构思加以等同替换或改变,都应涵盖在本发明的保护范围之内。
Claims (6)
1.含硼氮的杂环化合物,其特征在于,所述含硼氮的杂环化合物选自如下所示的化学结构中的一种:
2.权利要求1所述含硼氮的杂环化合物在有机电致发光器件中的应用,其作为有机电致发光器件的磷光发光主体材料或热延迟荧光发光材料。
3.一种有机材料,其包含权利要求1所述含硼氮的杂环化合物的一种或多种。
4.一种有机电致发光器件,其包含权利要求1所述含硼氮的杂环化合物的一种或多种或者权利要求3所述有机材料。
5.根据权利要求4所述的有机电致发光器件,其特征在于,包括基板、第一电极、包含发光层和第二电极元件,所述含硼氮的杂环化合物或者所述有机材料作为所述发光层的磷光发光主体材料或热延迟荧光发光材料。
6.一种显示或照明装置,其特征在于,包括权利要求4或5所述的有机电致发光器件。
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105431439A (zh) * | 2014-02-18 | 2016-03-23 | 学校法人关西学院 | 多环芳香族化合物 |
CN108431984A (zh) * | 2016-02-10 | 2018-08-21 | 学校法人关西学院 | 延迟荧光有机电场发光元件 |
CN112442052A (zh) * | 2019-08-29 | 2021-03-05 | 南京高光半导体材料有限公司 | 一种高效率、长寿命的蓝色荧光掺杂材料及其应用和有机电致发光器件 |
CN113135946A (zh) * | 2020-01-17 | 2021-07-20 | 学校法人关西学院 | 多环芳香族化合物或多环芳香族化合物的多聚体、包含其的化合物、交联体、材料及装置 |
CN114524833A (zh) * | 2022-02-18 | 2022-05-24 | 武汉华星光电半导体显示技术有限公司 | 发光材料、有机电致发光器件、显示设备及照明设备 |
CN115246852A (zh) * | 2021-04-28 | 2022-10-28 | 上海弗屈尔光电科技有限公司 | 一种有机硼化合物及含其的有机光电元件与应用 |
CN115651003A (zh) * | 2021-07-07 | 2023-01-31 | 浙江光昊光电科技有限公司 | 一种氮杂硼杂稠环化合物及其在有机电子器件中应用 |
-
2022
- 2022-05-18 CN CN202210539293.5A patent/CN114716467B/zh active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105431439A (zh) * | 2014-02-18 | 2016-03-23 | 学校法人关西学院 | 多环芳香族化合物 |
CN108431984A (zh) * | 2016-02-10 | 2018-08-21 | 学校法人关西学院 | 延迟荧光有机电场发光元件 |
CN112442052A (zh) * | 2019-08-29 | 2021-03-05 | 南京高光半导体材料有限公司 | 一种高效率、长寿命的蓝色荧光掺杂材料及其应用和有机电致发光器件 |
CN113135946A (zh) * | 2020-01-17 | 2021-07-20 | 学校法人关西学院 | 多环芳香族化合物或多环芳香族化合物的多聚体、包含其的化合物、交联体、材料及装置 |
JP2021113188A (ja) * | 2020-01-17 | 2021-08-05 | 学校法人関西学院 | 多環芳香族化合物 |
CN115246852A (zh) * | 2021-04-28 | 2022-10-28 | 上海弗屈尔光电科技有限公司 | 一种有机硼化合物及含其的有机光电元件与应用 |
CN115651003A (zh) * | 2021-07-07 | 2023-01-31 | 浙江光昊光电科技有限公司 | 一种氮杂硼杂稠环化合物及其在有机电子器件中应用 |
CN114524833A (zh) * | 2022-02-18 | 2022-05-24 | 武汉华星光电半导体显示技术有限公司 | 发光材料、有机电致发光器件、显示设备及照明设备 |
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