CN115433217B - 一种咔唑稠合的硼氮衍生物及其制备方法和应用 - Google Patents
一种咔唑稠合的硼氮衍生物及其制备方法和应用 Download PDFInfo
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- CN115433217B CN115433217B CN202210969389.5A CN202210969389A CN115433217B CN 115433217 B CN115433217 B CN 115433217B CN 202210969389 A CN202210969389 A CN 202210969389A CN 115433217 B CN115433217 B CN 115433217B
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- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims description 16
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
- 239000013067 intermediate product Substances 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical group BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical group [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 8
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- 239000003513 alkali Substances 0.000 claims description 4
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- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
- C09K2211/107—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with other heteroatoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
- C09K2211/1085—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms with other heteroatoms
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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Abstract
本发明属于有机合成领域,具体涉及一种咔唑稠合的硼氮衍生物及其制备方法和应用。本发明提出了一种新型咔唑稠合的硼氮衍生物的制备方法及其在高效有机电致发光器件中的应用。通过巧妙的路线设计,可以高效合成具有DABNA‑1咔唑的稠合结构的硼氮衍生物TCZ‑F‑DABNA,不仅可以有效地实现光谱的较大红移,且能在一定程度上增强分子的扭曲,有利于制备高效,高色纯度且具有抗浓度淬灭的光电器件。该体系扩展了MR‑TADF材料分子库,推动了具有高效率、高色纯度以及具有抑制浓度淬灭效应的有机发光二极管的应用,为日后能设计更接近商业化需求的热活化延迟荧光OLED材料提供了一定的基础。
Description
技术领域
本发明属于有机合成领域,具体涉及一种咔唑稠合的硼氮衍生物及其制备方法和应用。
背景技术
有机发光二极管广泛应用于柔性屏显示,日常照明等领域,目前的柔性屏OLED屏主要是基于第二代磷光材料,且相关技术长期被日韩等公司垄断。当前的第三代的多重共振的热激活延迟荧光(MR-TADF)材料由于而有望开发具有更高色纯度和还原度的有机发光材料,相关研究将对增强未来国产的高清和超薄等显示技术,突破国外相关技术垄断优势起到重要的作用。
作为第三代有机发光材料,纯有机的热活化延迟荧光材料因其成本低廉,效率高等优点而成为当前的研究热点。为了保证有效的反响系间窜越的上转化过程,热活化延迟荧光材料常通过设计扭曲的D-A片段以实现较小的ΔESTs,但是这容易避免的导致分子弛豫的增加,影响了器件的色纯度。近年来提出的基于多重共振的分子设计策略为开发具有较高的辐射跃迁速率,较小的半峰宽以及更高的色纯度的器件提供了有效的解决思路。经过多年研究,目前多重共振体系的结构主要是以DABNA-1硼氮体系为母核,通过外围等基团的设计调控出具有更高性能的发光材料。但是目前的外围设计主要是以引入不同的非稠合的推拉电子基团为主,例如经典的叔丁基咔唑硼氮(BNCz)机器衍生物,但是这类材料的光色主要集中在蓝色到绿色区域。目前涉及到橙红光或红光范围的MR-TADF发光材料还是极少。此外,目前的MR-TADF材料还面临着严重的浓度淬灭等问题,这严重阻碍了其商业化应用。因此通过外围共轭结构的扩展有效实现光谱的较大红移以及设计扭曲的具有浓度淬灭效应的分子结构将是一个充满巨大挑战的策略。
发明内容
为了解决上述存在的技术问题,本发明提供一种咔唑稠合的硼氮衍生物,所述咔唑稠合的硼氮衍生物是在DABNA-1分子结构的基础上稠合一个或两个能扩宽分子共轭的咔唑,其化学式如式A、式B或式C所示:
其中,X选自氧、硫、硒、芴基或二苯基;
R1选自氢或叔丁基;
R2选自氢、氰基、甲基、叔丁基,二苯胺基,3,6-二叔丁基二苯胺基、2,6-(3,6-二叔丁基咔唑基)苯基、2,6-(3,6-二咔唑基)苯基、咔唑基、3,6-二叔丁基咔唑基、吩噻嗪基、吩噁嗪基或三嗪基衍生物。
本发明还提供一种上述咔唑稠合的硼氮衍生物的制备方法,包括如下步骤:
S1:将化合物Ⅰ、化合物Ⅱ、碱和钯催化剂加入有机溶剂中,一次反应,得到第一中间产物(PhCltBuInPz);所述化合物Ⅰ、化合物Ⅱ、碱和钯催化剂的摩尔比为1:1-3:2-12:0.04-0.1;
所述化合物Ⅰ的化学结构选自式C、式D或式E;所述化合物Ⅱ的化学结构为式F;所述第一中间产物的化学结构选自式G、式H或式J;所述式C、式D、式E、式F、式G、式H和式J如下所示:
其中,X选自氧、硫、硒、芴基或二苯基;
R1选自氢或叔丁基;
R2选自氢、氰基、甲基、叔丁基、二苯胺基、3,6-二叔丁基二苯胺基、2,6-(3,6-二叔丁基咔唑基)苯基、2,6-(3,6-二咔唑基)苯基、咔唑基、3,6-二叔丁基咔唑基、吩噻嗪基、吩噁嗪基或三嗪基衍生物;
S2:将有机锂试剂、化合物Ⅲ和所述中间产物混合,二次反应后得到第二中间产物;所述化合物Ⅲ为叔丁基苯、间二甲苯或间三甲苯;
S3:向所述第二中间产物中加入化合物Ⅳ,三次反应后得到第三中间产物;所述化合物Ⅳ为三溴化硼或三碘化硼;
S4:向所述第三中间产物中加入N,N-二异丙基乙胺,四次反应,除杂后得到所述咔唑稠合的硼氮衍生物;
所述有机锂试剂、化合物Ⅲ、化合物Ⅳ和N,N-二异丙基乙胺的摩尔比为1:1-5:1-5:1-5。
优选的,所述步骤S1中,有机溶剂包括甲苯、四氢呋喃、1,4-二氧六环或二甲亚砜溶剂。
优选的,所述步骤S1中,碱为叔丁醇钠、叔丁醇钾、碳酸钠、碳酸钾或碳酸铯;钯催化剂为Pd2(dba)3(三(二亚苄基丙酮)二钯)或Pd(OAc)2(醋酸钯),购自毕得医药。
优选的,所述步骤S1中,一次反应的温度为100-120℃,时间为10-14h。
优选的,所述步骤S1中,加入有机溶剂后,抽换氮气三次。
优选的,所述步骤S2中,有机锂试剂为叔丁基锂或正丁基锂。
优选的,所述步骤S2中,二次反应的温度为50-70℃,时间为2-3h。
优选的,所述步骤S3中,三次反应的温度为室温,时间为1-2h。
优选的,所述步骤S4中,四次反应的温度为120-140℃,时间为10-20h。
所述N,N-二异丙基乙胺由于调节pH。
优选的,所述步骤S4中,除杂的方法为加PBS水溶液淬灭,DCM(二氯甲烷)萃取,干燥,旋干后PE(石油醚)柱层析。
本发明还提供一种有机电致发光器件,包括上述的咔唑稠合的硼氮衍生物。所述有机电致发光器件,包括玻璃基板、空穴传输层、电子阻挡层、发光层、电子传输层和阴极层;所述玻璃基板上,设有有机化合物层依次成膜形成的空穴传输层、电子阻挡层、发光层和电子传输层,然后成膜阴极层。
本发明的技术方案相比现有技术具有以下优点:
本发明提出了一类新型咔唑稠合的硼氮衍生物的制备方法,并将其应用于有机电致发光器件中,获得了极佳的效果。该体系扩展了MR-TADF材料分子库,推动了具有高效率、高色纯度以及具有抑制浓度淬灭效应的有机发光二极管的应用,为日后能设计更接近商业化需求的热活化延迟荧光OLED材料提供了一定的基础。
附图说明
图1为咔唑稠合的硼氮衍生物的化学式示意图。
图2为合成咔唑稠合的硼氮衍生物的原料和中间产物的化学式示意图。
图3为有机电致发光器件的结构示意图。
附图标记说明:1-玻璃基板,2-空穴传输层,3-电子阻挡层,4-发光层,5-电子传输层,6-阴极层。
具体实施方式
下面结合附图和具体实施例对本发明作进一步说明,以使本领域的技术人员可以更好地理解本发明并能予以实施,但所举实施例不作为对本发明的限定。
实施例1
6,9,16,19-叔丁基-3b,10b,13b-三氮杂-20b-硼基芴[1,9-ab:1',9'-jk]苝(BNtBuInPz)的合成路线
BNtBuInPz的合成路线
①中间体tCzPhCltBuInPz:将原料1a(3.69g,10.0mmol),tBuInPz(4.69g,10.0mmol),Pd2(dba)3(275mg,0.30mmol),叔丁醇钠(1.92g,20.0mmol)加入到250mL二口烧瓶中,置换N2保护后,加入甲苯(100mL),继续抽换氮气三次后,加入四氟硼酸三叔丁基膦(580mg,2.0mmol),110℃回流反应12h,TLC显示原料1a消失,加水淬灭,DCM萃取,干燥,旋干,PE:DCM=10:1柱层析,得黄色固体PhCltBuInPz(5.45g,72%)。
产物表征:1H NMR(400MHz,CD2Cl2):δ8.08(d,J=1.9Hz,2H),7.93(s,1H),7.85–7.37(m,8H),7.36–7.32(m,1H),7.04(d,J=8.5Hz,1H),6.93(dd,J=8.7,2.4Hz,1H),6.70(d,J=37.7Hz,2H),6.03(d,J=7.9Hz,1H),5.69(s,1H),1.37–1.34(m,27H),1.21(s,9H).13C NMR(101MHz,CD2Cl2):δ146.49,143.38,143.33,139.23,139.10,138.68,131.35,130.13,123.89,123.76,123.46,123.40,116.57,114.19,113.89,109.40,109.22,103.30,34.84,34.72,34.69,31.80,31.69,31.48.MALDI-TOF:Calculated:755.401,Found:755.65.
②将原料tCzPhCltBuInPz(7.56g,10.0mmol)加入到100mL二口烧瓶中,置换N2保护后,加入无水叔丁基苯(30mL),抽换氮气三次后,于-40℃低温下加入叔丁基锂(1.3mol/Lin pentane,19.0mL,25.0mmol),移走低温浴,60℃反应2h。-40℃下缓慢加入三溴化硼(2.40mL,25.0mmol),室温反应1h。冰浴下加入N,N-二异丙基乙胺(3.50mL,25.0mmol),130℃反应过夜。取样TLC显示原料PhCltBuInPz消失,有新点生成,加PBS水溶液淬灭,DCM萃取,干燥,旋干,PE柱层析,得黄色固体BNtBuInPz(5.69mg,78%)。
产物表征:1H NMR(400MHz,CD2Cl2):δ8.80(d,J=1.9Hz,1H),8.53(d,J=1.9Hz,1H),8.36(d,J=8.8Hz,1H),8.32(d,J=2.0Hz,1H),8.26(s,1H),8.14(d,J=2.0Hz,3H),7.96(s,1H),7.90(d,J=7.7Hz,1H),7.80(s,1H),7.75–7.66(m,3H),7.66–7.61(m,1H),7.33(s,1H),1.68(s,9H),1.57(s,9H),1.52(s,9H),1.46(s,9H).13C NMR(101MHz,CD2Cl2):δ146.15,145.28,144.81,144.62,142.51,141.72,138.13,137.23,132.84,129.32,128.43,126.87,126.45,124.41,124.04,123.48,123.27,123.03,120.62,117.46,117.24,114.09,113.91,113.81,112.01,35.18,35.08,34.70,34.67,34.62,34.56,31.93,31.61,31.59,31.55,29.04,26.92,25.24,20.41,19.18,11.18.MALDI-TOF:Calculated:729.425,Found:729.649.
实施例2
TCZ-F-DABNA的合成路线
①中间体PhCltBuInPz:将原料2a(1.75g,6.0mmol),tBuInPz(5.75g,15.6mmol),Pd2(dba)3(357mg,0.39mmol),叔丁醇钠(2.50g,26.0mmol)加入到250mL二口烧瓶中,置换N2保护后,加入甲苯(100mL),继续抽换氮气三次后,加入四氟硼酸三叔丁基膦(1.13g,3.90mmol),110℃回流反应12h,TLC显示原料2-氯-1,3-二溴苯消失,加水淬灭,DCM萃取,干燥,旋干,PE:DCM=10:1柱层析,得黄色固体PhCltBuInPz(3.92g,71%)。
产物表征:1HNMR(400MHz,CD2Cl2):1HNMR(400MHz,CD2Cl2):δ7.93(d,J=1.9Hz,2H),7.75(ddd,J=9.2,6.7,4.2Hz,3H),7.67(t,J=8.4Hz,2H),7.53(dd,J=8.0,1.5Hz,2H),7.46(dd,J=8.9,2.0Hz,2H),7.16(s,2H),6.74(t,J=7.7Hz,2H),6.60(dt,J=15.9,7.8Hz,2H),5.97–5.59(m,4H),1.35(s,18H),1.17(s,18H).13C NMR(101MHz,CD2Cl2):δ146.46,146.40,143.33,139.14,135.53,134.10,131.70,130.30,129.39,123.66,121.93,121.88,121.42,117.10,114.18,113.71,113.58,111.95,103.31,103.23,34.77,34.59,31.63,31.57,31.38.MALDI-TOF:Calculated:844.427,Found:844.682.
②将原料PhCltBuInPz(1.20g,1.42mmol)加入到100mL二口烧瓶中,置换N2保护后,加入无水叔丁基苯(30mL),抽换氮气三次后,于-40℃低温下加入叔丁基锂(1.3mol/Linpentane,2.75mL,3.55mmol),移走低温浴,60℃反应2h。-40℃下缓慢加入三溴化硼(0.34mL,3.50mmol),室温反应1h。冰浴下加入N,N-二异丙基乙胺(0.56mL,3.50mmol),130℃反应过夜。取样TLC显示原料PhCltBuInPz消失,有新点生成,加PBS水溶液淬灭,DCM萃取,干燥,旋干,PE柱层析,得黄色固体BNtBuInPz(954mg,82%)。
产物表征:1HNMR(400MHz,CDCl3):δ8.11(d,J=1.9Hz,2H),7.88(dd,J=35.5,8.1Hz,8H),7.72(s,4H),7.62–7.48(m,3H),7.17(s,2H),1.49(s,18H),1.45(s,18H).13CNMR(101MHz,CDCl3):δ146.08,144.47,134.47,132.89,128.07,127.58,126.57,123.95,123.28,122.92,117.42,114.19,113.91,111.91,35.32,34.81,31.96,31.90,31.78,29.73.MALDI-TOF:Calculated:818.452,Found:818.697.
实施例3
以实施例2为荧光掺杂染料的有机电致发光器件的制作与性能评价
使用3mm宽的氧化铟锡(ITO)膜图案的成条纹状的、带有ITO透明电极的玻璃板作为基板。用异丙醇将玻璃基板洗涤后,通过臭氧紫外线进行表面处理。在洗涤后的基板上用真空蒸镀法进行各层的真空蒸镀,制作剖面图如图3所示的发光面积9mm2的有机电致发光器件。
首先,将前述玻璃基板导入真空蒸镀槽内,减压至1×10-4Pa。然后在图1中所示的玻璃基板1上,作为有机化合物层依次成膜成空穴传输层2、电子阻挡层3、发光层4和电子传输层5,然后成膜阴极层6。以30nm厚的膜厚真空蒸镀的4,4'-环己基二[N,N-二(4-甲基苯基)苯胺](TAPC)和10nm厚的膜厚真空蒸镀的4,4',4”-三(咔唑-9-基)三苯胺(TCTA)作为空穴传输层2,以10nm厚的膜厚真空蒸镀的1,3-二-9-咔唑基苯(mCP)为电子阻挡层3,以20nm厚的膜厚真空蒸镀比例为92:8(质量%)的9-(2-(9-苯基-9H-咔唑-3-基)苯基)-9H-3,9'-联咔唑(PhCzBCz)与本发明实施例2中合成的产物作为发光层4,以40nm厚的膜厚真空蒸镀的3,3'-[5'-[3-(3-吡啶基)苯基][1,1':3',1”-三联苯]-3,3”-二基]二吡啶(TmPyPb)作为电子传输层5。其中各个有机材料通过电阻加热方式成膜。加热化合物以0.3-0.5nm的成膜速率真空蒸镀。最后以与ITO条纹正交的方式配置金属掩膜,构成膜阴极6。阴极层6是分别以1nm和100nm的膜厚真空蒸镀氟化锂和铝而形成的两层结构。各个膜厚用触针式膜厚测定器(DEKTAK)测定。进而,将器件密封在水和氧分浓度1ppm以下的氮气氛手套箱内。密封使用玻璃质的密封盖和前述成膜基板环氧性紫外线固化树脂(Nagase ChemteX Corporation制造)。
对所制备的有机电致发光器件施加直流电流,使用Spectrascan PR650亮度计来评价发光性能,使用电脑控制的Keithley 2400数字源表测量电流-电压特性。作为发光特性,测定在随外加直流电压变化下的CIE色坐标值、最大亮度(cd/m2)、外量子效率(%)、功率效率(lm/W)。所制作的器件的测定值为(0.54,0.44),12740cd/m2,39.2%和108.1lm/W。且在30wt%的高掺杂浓度下器件仍然实现了30.3%的EQE(外量子效率)。
效果评价1
为了设计出具有较高效率、高色纯度以及能够在一定程度上抑制浓度淬灭的具有商业化应用潜力的优秀器件,基于DABNA-1母核体系优良的光电性能,结合稠合咔唑在不明显影响MR效应的前提下具有扩宽分子共轭作用,且外围稠合结构在较大程度上增大了分子结构的扭曲的效果。提出了一种新型咔唑稠合的硼氮衍生物的制备方法及其在高效有机电致发光器件中的应用。通过巧妙的路线设计,可以高效合成具有DABNA-1咔唑的稠合结构的硼氮衍生物TCZ-F-DABNA,不仅可以有效地实现光谱的较大红移,且能在一定程度上增强分子的扭曲,有利于制备高效,高色纯度且具有抗浓度淬灭的光电器件。结果表明,TCZ-F-DABNA中咔唑的引入不仅增强扩宽了分子的共轭结构,同时保证了器件较小的半峰宽(FWHM=62nm)。最终制备的器件在8wt%的掺杂下实现了588nm的橙红光发光以及最大39.2%的电致发光效率,且当掺杂浓度提升到30wt%时,器件仍然保持了超过30%的电致发光效率。
显然,上述实施例仅仅是为清楚地说明所作的举例,并非对实施方式的限定。对于所属领域的普通技术人员来说,在上述说明的基础上还可以做出其它不同形式变化或变动。这里无需也无法对所有的实施方式予以穷举。而由此所引申出的显而易见的变化或变动仍处于本发明创造的保护范围之中。
Claims (10)
1.一种咔唑稠合的硼氮衍生物,其特征在于,所述咔唑稠合的硼氮衍生物是在DABNA-1分子结构的基础上稠合一个或两个能扩宽分子共轭的咔唑,其化学式如下:
。
2.一种权利要求1所述咔唑稠合的硼氮衍生物的制备方法,其特征在于,包括如下步骤:
S1:将化合物Ⅰ、化合物Ⅱ、碱和钯催化剂加入有机溶剂中,一次反应,得到第一中间产物;所述化合物Ⅰ、化合物Ⅱ、碱和钯催化剂的摩尔比为1:1-3:2-12:0.04-0.1;
所述化合物Ⅰ的化学结构如式2a所示,所述化合物Ⅱ的化学结构如式2所示:
,/>;
所述第一中间产物的化学结构如下:
;
S2:将有机锂试剂、化合物Ⅲ和所述中间产物混合,二次反应后得到第二中间产物;所述化合物Ⅲ为叔丁基苯;
S3:向所述第二中间产物中加入化合物Ⅳ,三次反应后得到第三中间产物;所述化合物Ⅳ为三溴化硼;
S4:向所述第三中间产物中加入N,N-二异丙基乙胺,四次反应,除杂后得到所述咔唑稠合的硼氮衍生物;
所述有机锂试剂、化合物Ⅲ、化合物Ⅳ和N,N-二异丙基乙胺的摩尔比为1:1-5:1-5:1-5。
3.如权利要求2所述的制备方法,其特征在于,所述步骤S1中,有机溶剂包括甲苯、四氢呋喃、1,4-二氧六环或二甲亚砜溶剂。
4.如权利要求2所述的制备方法,其特征在于,所述步骤S1中,碱为叔丁醇钠、叔丁醇钾、碳酸钠、碳酸钾或碳酸铯;钯催化剂为三(二亚苄基丙酮)二钯或醋酸钯。
5.如权利要求2所述的制备方法,其特征在于,所述步骤S1中,一次反应的温度为100-120℃,时间为10-14 h。
6.如权利要求2所述的制备方法,其特征在于,所述步骤S2中,有机锂试剂为叔丁基锂或正丁基锂。
7.如权利要求2所述的制备方法,其特征在于,所述步骤S2中,二次反应的温度为50-70℃,时间为2-3 h。
8.如权利要求2所述的制备方法,其特征在于,所述步骤S3中,三次反应的温度为室温,时间为1-2 h。
9.如权利要求2所述的制备方法,其特征在于,所述步骤S4中,四次反应的温度为120-140℃,时间为10-20 h。
10.一种有机电致发光器件,其特征在于,包括权利要求1所述的咔唑稠合的硼氮衍生物。
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