CN114656466B - 基于苯并稠合咔唑及吲哚咔唑衍生物及其有机电致发光器件应用 - Google Patents
基于苯并稠合咔唑及吲哚咔唑衍生物及其有机电致发光器件应用 Download PDFInfo
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- CN114656466B CN114656466B CN202210398330.5A CN202210398330A CN114656466B CN 114656466 B CN114656466 B CN 114656466B CN 202210398330 A CN202210398330 A CN 202210398330A CN 114656466 B CN114656466 B CN 114656466B
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- carbazole
- indolocarbazole derivative
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 title claims abstract description 44
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 117
- 239000000463 material Substances 0.000 claims abstract description 20
- 238000002347 injection Methods 0.000 claims description 9
- 239000007924 injection Substances 0.000 claims description 9
- 230000005525 hole transport Effects 0.000 claims description 8
- 230000005693 optoelectronics Effects 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 5
- 238000001228 spectrum Methods 0.000 abstract description 5
- 230000002093 peripheral effect Effects 0.000 abstract description 3
- 230000001276 controlling effect Effects 0.000 abstract description 2
- 230000001105 regulatory effect Effects 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 description 36
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 35
- 239000010410 layer Substances 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
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- 238000000921 elemental analysis Methods 0.000 description 12
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 229920005547 polycyclic aromatic hydrocarbon Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
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- 229910052711 selenium Inorganic materials 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical class [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
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- 229940005605 valeric acid Drugs 0.000 description 1
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Abstract
本发明属于有机发光材料领域，具体公开了基于苯并稠合咔唑及吲哚咔唑衍生物及其有机电致发光器件应用，苯并稠合咔唑及吲哚咔唑衍生物的化学结构如式(1)与式(2)所示，该类化合物可以作为高效的发光材料，也可作为给电子单元，外围进一步接枝受体基团有希望发展为TADF材料。该类材料合成简单，刚性骨架便于减小发射FWHM，为发展窄FWHM材料的提供了新策略。在纯碳氢骨架中嵌入氮原子，提高了热稳定性以及发光效率。通过调控外围挂接基团，光谱易于调节。采用该类化合物制备的OLED器件电致发光光谱具有低启动电压、高发光色纯度、高发光效率，有良好的应用前景。
Description
技术领域
本发明属于有机发光材料领域，主要涉及一类苯并稠合咔唑及吲哚咔唑衍生物的有机发光材料及其应用，以及包含该类化合物的有机电致发光器件。
背景技术
有机发光二极管(OLED)已成功用作显示和照明的发光器件，因为它们可以通过设计发光材料来实现高效的电致发光器件。尽管有机发光材料具有易于合成、成本低、颜色可调性等明显优点，但目前已商业化的OLED的半峰宽(FWHM)大于60nm，这并不利于显示时高色纯度的要求。最近开发的基于多重共振(MR)效应的分子通过在多环芳烃(PAH)体系中嵌入供电子原子和吸电子原子，使前线轨道在刚性π共轭骨架内交替分布，在窄发射光谱方面显示出巨大的潜力。多环芳烃族和杂芳烃族化合物一般具有给电子、吸电子、发光与半导体等等特性，该类化合物其中还包含氮平面和非平面多环稠合芳族化合物，尤其是吡咯、吲哚或咔唑作为杂环部分的骨架作为电子供体同样重要。因此，有待于进一步开发其他多环芳烃族化合物，并探索其在OLED中实现窄FWHM的可行性。
发明内容
基于上述现有技术的不足，本发明目的在于提供一类苯并稠合咔唑及吲哚咔唑衍生物，模拟其前线轨道分布方式，探究其发射波长、FWHM和荧光量子产率(PLQY)的变化。
一类苯并稠合咔唑及吲哚咔唑衍生物的化学结构如式(1)与式(2)所示，
其中：
所述R1、R2、R3、R4、R5、R6、R7、R8分别独立地表示单取代基到最大允许取代基，并且各自独立地选自氢、氘或者取代或未取代的下述基团中的一种：卤素、Cl-C36的链状烷基、C3-C36的环烷基、Cl-C10的烷氧基、Cl-C10的硫代烷氧基、羰基、羧基、硝基、氰基、氨基、C6-C30的芳基、C3-C30杂芳基、C6-C60的单环芳基、C6-C60的稠环芳基、C6-C60的芳氧基、C5-C60的单环杂芳基、C5-C60的稠环杂芳基中的一种。作为杂原子的具体例，可举出氮原子、氧原子、硫原子、硅原子、磷原子和硼原子。
所述R1、R2、R3、R4；R5、R6、R7、R8相邻的两个之间任选可通过单键连接或者可稠合而相互键合形成环。
X1-X15(即X1、X2、X3、X4、X5、X6、X7、X8、X9、X10、X11、X12、X13、X14、X15)可独立地选自碳原子、杂原子或者取代的下述基团中的一种：C1-C36的链状烷基、C3-C36的环烷基、C1-C10的烷氧基、C1-C10的硫代烷氧基、羰基、羧基、硝基、氰基、氨基、C6-C30的芳基、C3-C30杂芳基、C6-C60的单环芳基、C6-C60的稠环芳基、C6-C60的芳氧基、C5-C60的单环杂芳基、C5-C60的稠环杂芳基中的一种或这些基团的组合。作为杂原子的具体例，可举出氮原子、氧原子、硫原子、硅原子、磷原子和硼原子。
当上述基团存在取代基时，所述取代基团分别独立选自氢、氘或者取代或未取代的下述基团中的一种：卤素、C1-C36的链状烷基、C3-C36的环烷基、C1-C10的烷氧基、Cl-C10的硫代烷氧基、羰基、羧基、硝基、氰基、氨基、C6-C30的芳基、C3-C30杂芳基、C6-C60的单环芳基、C6-C60的稠环芳基、C6-C60的芳氧基、C5-C60的单环杂芳基、C5-C60的稠环杂芳基中的一种或这些基团的组合。
优选的，式(1)或式(2)中优选的，X1-X15均为碳原子且与相邻的R1、R2、R3、R4、R5、R6、R7、R8可通过单键或者可彼此稠合而相互键合形成环。
优选的，本发明化合物的具体通式如下式(3)至式(6)中的任一所示：
式(3)-式(6)中，R9-R20的定义均与在式(1)、(2)中R1定义相同。Ar1-Ar7分别独立表示C5-C20的芳香族、杂芳香族或者非芳香族环系、C4-C20单环杂环或稠合杂环中的任意一种。
本发明中，“取代的基团”指的是“取代或未取代”的基团被取代时取代基的选择范围，个数不做具体限定，只要满足化合物键要求即可，示例性地，可以为1个、2个、3个、4个或5个，且当取代基的个数为2个及以上时，这2个及以上取代基可以相同也可以不同；卤素代表氯原子、氟原子、溴原子等；Ca-Cb的表达方式代表该基团具有的碳原子数为a-b，除非特殊说明，一般而言该碳原子数不包括取代基的碳原子数；其中式(1)-式(6)的结构中的碳原子中可以替换成杂原子，所述的杂原子，通常是选自N、O、S、P、Si和Se中的原子或原子团，优选自N、O、S。本发明中所述的原子名称，包括其对应的各种同位素，例如，氢(H)则包括1H(氕或作H)、2H(氘或作D)等；碳(C)则包括12C、13C等。
本发明的式(3)所述的化合物可以优选出下述具体结构化合物，这些化合物仅为代表性的：
本发明的式(4)所述的化合物可以优选出下述具体结构化合物，这些化合物仅为代表性的：
式(5)所述的化合物可以优选出下述具体结构化合物，这些化合物仅为代表性的：
本发明的式(6)所述的化合物可以优选出下述具体结构化合物，这些化合物仅为代表性的：
本发明的另外一个目的是提供苯并稠合咔唑及吲哚咔唑衍生物有机发光材料的应用，将其作为发光层材料用于有机电致发光二极管，以提高发光色纯度以及发光效率。
基于苯并稠合咔唑及吲哚咔唑衍生物作为有机发光材料在有机光电器件中的应用。
其中有机光电器件中包括阳极层，空穴注入层、空穴传输层，发光层、电子传输层，阴极层；空穴注入层形成在阳极层上，所述空穴传输层形成在空穴注入层上，所述的阴极层形成在所述的电子传输层上，所述的空穴传输层与所述的电子传输层之间为发光层，其中，所述的发光层中含有上述基于苯并稠合咔唑及吲哚咔唑衍生物。
与现有技术相比，本发明的有益效果在于：本发明的新型的多环芳烃族化合物，具体为苯并稠合咔唑及吲哚咔唑衍生物，该类化合物可以作为高效的发光材料，也可作为给电子单元，外围进一步接枝受体基团有希望发展为TADF材料。该类材料合成简单，刚性骨架便于减小发射FWHM，为发展窄FWHM材料的提供了新策略。在纯碳氢骨架中嵌入氮原子，提高了热稳定性以及发光效率。通过调控外围挂接基团，光谱易于调节。采用该类化合物制备的OLED器件电致发光光谱具有低启动电压、高发光色纯度和高发光效率，有良好的应用前景。
附图说明
图1为本发明实施例7和实施例9中化合物7(图1a)和9(图1b)的单晶衍射结构示意图。
图2为本发明实施例3、6、7、8和9中化合物3、6、7、8和9分别在甲苯溶液中的紫外可见光吸收光谱图(Abs)。
图3为本发明实施例3、12、13、14和15中化合物3、12、13、14和15分别在甲苯溶液中的光致发光光谱图(PL)。
图4为本发明实施例6中化合物6在正己烷、甲苯、四氢呋喃、二氯甲烷和乙腈溶液中的光致发光光谱图。
图5为本发明实施例12中化合物12应用在电致发光器件中的电致发光谱图(EL)。
具体实施方式
为了更清楚的说明本发明，下面结合优选实施例和附图对本发明作进一步说明。本领域技术人员应当理解，下面所描述的具体内容是说明性的而非限制性的，不能因此限制本发明的保护范围。
本发明中，制备方法如无特殊说明均为常规方法。所用的原料如无特别说明均可以从公开的商业途径获得。
实施例1
本发明提供的式(3)中包含的化合物
具体合成路线如下：
化合物M1的合成方法为：在250mL两口烧瓶中依次加入咔唑(2.5g,15.0mmol),1-溴-2-氟苯(2.8g,15.5mmol),碳酸铯(6.5g,20.0mmol)和150mLN,N-二甲基甲酰胺，氮气氛围下搅拌加热至130℃反应12小时。反应完全后，将体系冷却至室温，倒入水中，减压抽滤，并用大量水洗滤渣，滤渣进一步用甲醇打浆，抽滤后得到4.4g化合物M1，收率92.0％。MS(EI):m/z 321.1[M+]。元素分析理论:C,66.04；H,3.59；N,4.53；实际:C,66.08；H,3.52；N,4.50。
化合物1的合成方法为：在250mL两口烧瓶中依次加入Ml(2.87g,8.0mmol)、苄基三乙基氯化铵(0.2g,0.8mmol)、碳酸钾(5.5g,40.0mmol)、三苯基膦、醋酸钯(0.26g,1.2mmol)、150mLN，N-二甲基乙酰胺，氮气保护下搅拌加热至150℃反应3小时。反应完全后，将体系冷却至室温，倒入水中，减压抽滤，并用大量水洗滤渣，将滤渣用二氯甲烷:石油醚＝1:20(体积比)的洗脱剂在硅胶柱上进行分离提纯，得到1.7g化合物1，收率89.5％。MS(EI):m/z 241.07[M+]。元素分析理论:C,89.60；H,4.60；N,5.80；实际:C,89.55；H,4.58；N,5.78。
实施例2
本发明提供的式(3)中包含的化合物
具体合成路线如下：
化合物M2的合成方法为：与化合物M1类似，其不同之处在于将1-溴-2-氟苯替换为2-氟-3-溴吡啶。目标化合物M2收率为85.4％。MS(EI):m/z 322.01[M+]。元素分析理论:C,63.18；H,3.43；N,8.67；实际:C,63.16；H,3.42；N,8.65。
化合物2的合成方法为：与化合物1类似，其不同之处在于将M1替换为M2。目标化合物2收率为83.2％。MS(EI):m/z 242.06[M+]。元素分析理论:C,84.28；H,4.16；N,11.56；实际:C,84.25；H,4.13；N,11.56。
实施例3
本发明提供的式(3)中包含的化合物
具体合成路线如下：
化合物M3的合成方法为：将1-溴-2,3,5,6-四氟苯(229mg,1.0mmol)、叔丁基咔唑(5.70g,4.5mmol)、碳酸铯(1.63g,5mmol)溶于N,N-二甲基酰亚胺并加入200ml单口瓶中，氮气保护下140℃反应20h。将反应体系内倒入水中，抽滤，用甲醇清洗上层，得到化合物5.3g化合物M3，收率为84.4％。MS(EI):m/z1264.86[M+]。元素分析理论:C,81.55；H,7.72；N,4.42；实际:C,81.52；H,7.63；N,4.41。
化合物3的合成方法为：与化合物1的合成方法类似，其不同之处在于将M1替换为M3。目标化合物3收率为75.9％。MS(EI):m/z 1184.72[M+]。元素分析理论:C,87.11；H,8.16；N,4.73；实际:C,87.05；H,8.12；N,4.71。
实施例4
本发明提供的式(4)中包含的化合物
具体合成路线如下：
化合物M4的合成方法为：将1,3-二溴-2,4-二氟苯(2.7g,10mmol)、咔唑(3.5g,21.0mmol)、碳酸铯(9.7g,30mmol)溶于N,N-二甲基酰亚胺并加入200ml单口瓶中，氮气保护下150℃反应20h。将反应体系内倒入水中，抽滤，用甲醇清洗上层，得到3.7g化合物M4，收率为65.2％。MS(EI):m/z 565.98[M+]。元素分析理论:C,63.63；H,3.20；N,4.95；实际:63.61；H,3.20；N,4.93。
化合物4的合成方法为：与化合物1类似，其不同之处在于将M1替换为M4。目标化合物4收率为20.3％。MS(EI):m/z 404.13[M+]。元素分析理论:C,89.09；H,3.99；N,6.93；实际:C,89.04；H,3.95；N,6.91。
实施例5
本发明提供的式(5)中包含的化合物
具体合成路线如下：
式M5的合成方法为：与化合物M4类似，其不同之处在于将1,3-二溴-2,4-二氟苯换成了1,2-二溴-3,6-二氟苯，目标化合物M5收率为90.8％。MS(EI):m/z 565.98[M+]。元素分析理论:C,63.63；H,3.20；N,4.95；实际:63.61；H,3.20；N,4.93。
化合物5的合成方法为：将M5(5.7g,10mmol)、三氟乙酸钯(II)(0.3g,1mmol)、乙酸银(10.0g,60mmol)和叔戊酸加入500ml单口瓶，然后在空气中在160℃下搅拌48小时。冷却至室温后，加入水并将混合物通过硅藻土垫过滤，用二氯甲烷洗脱。将滤液倒入饱和碳酸氢钠水溶液中(20mL)并用二氯甲烷(20mL×3)萃取。将残余物进行硅胶柱层析(洗脱液：石油醚/二氯甲烷＝4/1)，得到化合物5。目标化合物5的收率为44.6％。MS(EI):m/z 404.12[M+]。元素分析理论:C,89.09；H,3.99；N,6.93；实际:C,89.04；H,3.95；N,6.91。
实施例6
本发明提供的式(6)中包含的化合物
具体合成路线如下：
化合物M6的合成方法为：将1,2,3-三氟苯(792mg,6mmol)、11,12-二氢吲哚并[2,3-a]咔唑(1.28g,5mmol)、碳酸铯(3.26g,10mmol)溶于N,N-二甲基甲酰胺并加入耐高压反应瓶中，氩气保护下150℃反应10h。将反应体系内倒入水中，抽滤，用甲醇清洗上层滤渣，得黄色滤渣。将黄色滤渣硅胶柱层析(石油醚：二氯甲烷＝4：1)得到402mg淡黄色固体化合物M6，收率19.17％。MS(EI):m/z 348.38[M+]。元素分析理论:C,82.74；H,3.76；N,8.04；实际:C,82.73；H,3.76；N,8.02。
化合物6的合成方法为：将化合物M6(640mg,1.84mmol)、3,6-叔丁基咔唑(565mg,2.02mmol)、碳酸铯(1.20g,3.68mmol)溶于N,N-二甲基甲酰胺并加入单口瓶中，氮气下150℃反应12h。将反应体系内倒入水中，抽滤，用甲醇清洗上层滤渣，得淡黄色滤渣。将淡黄色滤渣硅胶柱层析(石油醚：二氯甲烷＝4：1)得到950mg淡黄色固体化合物6，收率84.95％。MS(EI):m/z 607.77[M+]。元素分析理论:C,86.95；H,6.14；N,6.91；实际:C,86.93；H,6.15；N,6.91。
实施例7
本发明提供的式(6)中包含的化合物
具体合成路线如下：
化合物M7的合成方法为：与化合物M6类似，具体不同之处在于将1,2,3-三氟苯换成1,2,3,4-四氟苯。目标化合物M7的收率为84.2％。MS(EI):m/z 366.37[M+]。元素分析理论:C,78.68；H,3.30；N,7.65；实际:C,78.62；H,3.30；N,7.59。
化合物7的合成方法为：与化合物6类似，具体不同之处在于将化合物M6换成M7。目标化合物7的收率为82.7％。MS(EI):m/z 885.17[M+]。元素分析理论:C,86.84；H,6.83；N,6.33；实际:C,86.82；H,6.82；N,6.31。
实施例8
本发明提供的式(6)中包含的化合物
具体合成路线如下：
化合物M8的合成方法为：与化合物M7类似，具体不同之处在于将1,2,3,4-四氟苯换成1,2,4,5-四氟苯。目标化合物M8的收率为82.55％。MS(EI):m/z 366.37[M+]。元素分析理论:C,78.68；H,3.30；N,7.65；实际:C,78.62；H,3.30；N,7.59。
化合物8的合成方法为：与化合物7类似，具体不同之处在于将化合物M7换成M8。目标化合物8的收率为81.7％。MS(EI):m/z 885.17[M+]。元素分析理论:C,86.84；H,6.83；N,6.33；实际:C,86.82；H,6.82；N,6.31。
实施例9
本发明提供的式(6)中包含的化合物
具体合成路线如下：
化合物M9的合成方法为：与化合物M8类似，具体不同之处在于将1,2,4,5-四氟苯换成六氟苯。目标化合物M9的收率为70.4％。MS(EI):m/z 402.33[M+]。元素分析理论:C,71.64；H,2.51；N,6.96；实际:C,71.61；H,2.51；N,6.91。
化合物9的合成方法为：与化合物8类似，具体不同之处在于将化合物M8换成M9。目标化合物9的收率为74.2％。MS(EI):m/z 1413.96[M+]。元素分析理论:C,86.64；H,7.41；N,5.94；实际:C,86.63；H,7.41；N,5.94。
实施例10
本发明提供的式(6)中包含的化合物
具体合成路线如下：
化合物M10的合成方法为：与化合物M6类似，具体不同之处在于将1,2,3-三氟苯换成1-溴-2,3-二氟苯。目标化合物M10的收率为20.2％。MS(EI):m/z409.23[M+]。元素分析理论:C,70.43；H,3.20；N,6.84；实际:C,70.43；H,3.20；N,6.82。
化合物10的合成方法为：将M10(409mg,1.0mmol)、2,4-二苯基-6-[4-(4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷-2-基)苯基]-1,3,5-三嗪(478mg,1.1mmol)、碳酸钠(4.1g,4.0mmol)和四(三苯基膦)钯(0.06g,0.05mmol)溶于40mL甲苯、6.4mL乙醇、8mL水加入100ml单口瓶。氮气保护下106℃搅拌过夜。将反应冷却至室温后，混合物用水稀释，再用乙酸乙酯萃取水层。有机相用无水硫酸钠干燥后，旋干除去溶剂得粗产物。使用硅胶柱层析(石油醚：乙酸乙酯＝4:1)作为洗脱剂分离提纯得546mg化合物10，产率为85.6％。MS(EI):m/z637.02[M+]。元素分析理论:C,84.75；H,4.27；N,10.98实际:C,84.65；H,4.27；N,10.92。
实施例11
本发明提供的式(6)中包含的化合物
具体合成路线如下：
化合物M11的合成方法为：与化合物M6类似，具体不同之处在于将1,2,3-三氟苯换成2,3,6-三氟吡啶。目标化合物M11的收率为74.2％。MS(EI):m/z349.37[M+]。元素分析理论:C,79.07；H,3.46；N,12.03；实际:C,79.02；H,3.44；N,12.03。
化合物11的合成方法为：与化合物6类似，具体不同之处在于将化合物M6换成M11。目标化合物11的收率为73.7％。MS(EI):m/z 496.51[M+]。元素分析理论:C,84.66；H,4.06；N,11.28；实际:C,84.62；H,4.06；N,11.24。
实施例12
本发明提供的式(6)中包含的化合物
具体合成路线如下：
化合物M12的合成方法为：与化合物M8类似，目标化合物M12的收率为78.33％。MS(EI):m/z523.12[M+]。元素分析理论:C,55.00；H,1.92；N,5.34；实际:C,54.98；H,1.90；N,5.31。
化合物M13的合成方法为：与化合物8类似，目标化合物M13的收率为79.96％。MS(EI):m/z818.51[M+]。元素分析理论:C,70.43；H,3.20；N,6.84；实际:C,70.40；H,3.15；N,6.79。
化合物12的合成方法为：与化合物1类似，目标化合物12的收率为15.7％。MS(EI):m/z 656.69[M+]。元素分析理论:C,87.79；H,3.68；N,8.53；实际:C,87.71；H,3.64；N,8.52。
实施例13
本发明提供的式(6)中包含的化合物
具体合成路线如下：
化合物M14的合成方法为：化合物M8类似，目标化合物M14的收率为82.32％。MS(EI):m/z 366.03[M+]。元素分析理论:C,78.68；H,3.30；N,7.65；实际:C,78.63；H,3.20；N,7.62。
化合物M15的合成方法为：化合物M13类似，目标化合物M15的收率为80.62％。MS(EI):m/z 573.04[M+]。元素分析理论:C,75.27；H,3.51；N,7.31；实际:C,75.24；H,3.55；N,7.32。
化合物13的合成方法为：与化合物12类似，目标化合物13的收率为24.7％。MS(EI):m/z 493.52[M+]。元素分析理论:C,87.61；H,3.88；N,8.51；实际:C,87.51；H,3.68；N,8.50。
实施例14
本发明提供的式(6)中包含的化合物
具体合成路线如下：
化合物M16的合成方法为：化合物M8类似，目标化合物M16的收率为80.62％。MS(EI):m/z 366.29[M+]。元素分析理论:C,78.68；H,3.30；N,7.65；实际:C,78.66；H,3.36；N,7.62。
化合物M17的合成方法为：化合物M13类似，目标化合物M17的收率为72.91％。MS(EI):m/z 818.02[M+]。元素分析理论:C,70.43；H,3.20；N,6.84；实际:C,70.41；H,3.24；N,6.82。
化合物14的合成方法为：与化合物12类似，目标化合物14的收率为24.7％。MS(EI):m/z 656.76[M+]。元素分析理论:C,87.79；H,3.68；N,8.53；实际:C,87.73；H,3.62；N,8.51。
实施例15
本发明提供的式(6)中包含的化合物
具体合成路线如下：
化合物M18的合成方法为：化合物M8类似，目标化合物M18的收率为68.37％。MS(EI):m/z 464.12[M+]。元素分析理论:C,85.32；H,4.56；N,6.03；实际:C,85.34；H,4.52；N,6.01。
化合物M19的合成方法为：化合物M13类似，目标化合物M19的收率为80.62％。MS(EI):m/z 366.29[M+]。元素分析理论:C,78.68；H,3.30；N,7.65；实际:C,78.66；H,3.36；N,7.62。
化合物15的合成方法为：与化合物12类似，目标化合物15的收率为12.7％。MS(EI):m/z 609.72[M+]。元素分析理论:C,88.64；H,4.46；N,6.89；实际:C,88.61；H,4.42；N,6.85。
实施例16
本发明提供的式(6)中包含的化合物
具体合成路线如下：
化合物M20的合成方法为：在0℃下，将液溴(1.27g,7.95mmol)在30mL三氯甲烷中的滴加到化合物13(1.57g,3.18mmol)在300mL三氯甲烷中的悬浮液中。将所得混合物在0℃下搅拌1小时，并逐渐温热至室温反应12小时。反应结束后，反应混合物用饱和亚硫酸钠溶液处理。收集有机层并用过量水洗涤。将有机溶剂蒸发并使用三氯甲烷/乙醇重结晶，得到化合物M20，所得产物无需进一步纯化直接用于下一步。
化合物16的合成方法为：与化合物10类似，具体不同之处在于将2,4-二苯基-6-[4-(4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷-2-基)苯基]-1,3,5-三嗪换成4-硼酸三苯胺。目标化合物17的收率为17.7％。MS(EI):m/z 980.12[M+]。元素分析理论:C,88.23；H,4.63；N,7.15；实际:C,88.23；H,4.63；N,7.15。
本发明所涉及的新型多环芳烃族化合物，具体为苯并稠合咔唑及吲哚咔唑衍生物均可按照以上实施例所示类似的方法合成出来。所有目标分子均分子刚性，减小了分子振动，便于减小发射FWHM，为发展窄FWHM材料的提供了新策略；所得目标产物均大共轭平面，利于电子离域，增强振子强度，从而提高发光效率；该类化合物在纯碳氢骨架中嵌入氮原子，提高了热稳定性；还可以作为给电子单元，在外围进一步挂接吸电子单元，从而调节其发光颜色，且有望发展为TADF材料。本发明还提供了所涉及的部分该类化合物的紫外-可见吸收光谱以及光致发光光谱，以及在电致发光器件中的相关图谱信息。
实施例17
将16项实施例中制备的化合物全部溶解在甲苯中配成10-5M溶液，测试其紫外可见吸收光谱以及光致发光光谱。本实施例详细信息记录在表1中。
表1本发明实施例中制备的化合物的光物理参数
实施例18
将实施例6中制备的化合物6溶解在正己烷、甲苯、四氢呋喃、二氯甲烷与乙腈中并配成10-5M溶液，分别测试其光致发光光谱。如图4所示，化合物6在正己烷、甲苯、四氢呋喃、二氯甲烷与乙腈中的发射峰分别为406、408、409、410和411nm，可以发现从低极性溶剂到高极性溶剂的发光峰变化并不明显，说明化合物6的分子间电荷转移强度较弱。
实施例19
16项实施例中制备的化合物在有机电致发光器件中的应用。以实施例化合物1-16作为器件发光层掺杂剂，制备结构为ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/mCP(5nm)/mCP:10wt％化合物1-16(20nm)/TmPyPB(40nm)/LiF(0.5nm)/Al(150nm)的有机电致发光二极管。
其中，阳极材料为ITO；空穴注入层材料为HAT-CN，一般总厚度为5-30nm，本实施例为10nm；空穴传输层的材料为TAPC和TCTA，总厚度一般为5-500nm，本实施例TAPC为40nm，TCTA为10nm；电子阻挡层为mCP，一般总厚度在5-30nm，本例为5nm；mCP为有机发光层宽带隙的主体材料，本发明化合物1-16为染料且掺杂浓度为10wt％，有机发光层的厚度一般为1-200nm，本实施例为20nm；电子传输层的材料为TmPyPB，厚度一般为5-300nm，本实施例为40nm；电子注入层及阴极材料选择LiF(0.5nm)和金属铝(150nm)。本实施例详细数据记录在表2中。
表2本发明实施例中制备的化合物的电致发光器件的性能参数
尽管结合了优选实施例对本发明进行了说明，但本发明并不局限于上述实施例，应当理解所附权利要求概括了本发明的范围。在本发明构思的指导下，本领域的技术人员应当意识到，对本发明的各实施例方案所进行的一定的改变，都将被本发明的权利要求书的精神和范围所覆盖。
Claims (3)
1.一类基于苯并稠合咔唑及吲哚咔唑衍生物，其特征在于：所述的化合物为以下结构中的一种：
2.如权利要求1所述的基于苯并稠合咔唑及吲哚咔唑衍生物作为有机发光材料在有机光电器件中的应用。
3.如权利要求2所述的基于苯并稠合咔唑及吲哚咔唑衍生物的应用，其特征在于，所述有机光电器件中包括阳极层，空穴注入层、空穴传输层，发光层、电子传输层，阴极层；
所述的空穴注入层形成在阳极层上，所述空穴传输层形成在空穴注入层上，所述的阴极层形成在所述的电子传输层上，所述的空穴传输层与所述的电子传输层之间为发光层，其中，所述的发光层中含有权利要求1中任一所述的化合物。
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