CN113149809A - 9-([1,1’-联苯]-3-基)-9-苯基-2-溴芴及其合成方法 - Google Patents
9-([1,1’-联苯]-3-基)-9-苯基-2-溴芴及其合成方法 Download PDFInfo
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- KGAAAHYVNHFYOD-UHFFFAOYSA-N 2-bromo-9-phenyl-9-(3-phenylphenyl)fluorene Chemical compound C1=CC=C(C=C1)C2=CC(=CC=C2)C3(C4=CC=CC=C4C5=C3C=C(C=C5)Br)C6=CC=CC=C6 KGAAAHYVNHFYOD-UHFFFAOYSA-N 0.000 title claims description 15
- 238000001308 synthesis method Methods 0.000 title abstract description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 40
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 20
- USYQKCQEVBFJRP-UHFFFAOYSA-N 1-bromo-3-phenylbenzene Chemical group BrC1=CC=CC(C=2C=CC=CC=2)=C1 USYQKCQEVBFJRP-UHFFFAOYSA-N 0.000 claims abstract description 12
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 30
- 229940125904 compound 1 Drugs 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 9
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 8
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- 239000002904 solvent Substances 0.000 claims description 7
- 229940125782 compound 2 Drugs 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- -1 3-bromobiphenyl Grignard reagent Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
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- 238000001914 filtration Methods 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
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Abstract
Description
技术领域
本发明涉及一种芴类衍生物及其合成方法,尤其涉及一种9-([1,1’-联苯]-3-基)-9-苯基-2-溴芴及其合成方法,属有机化学合成领域。
背景技术
有机电致发光器件具有超薄、结构简单、能耗低、响应速度快、全固化和主动发光等特点,且材料选择范围广、成本低。因此有机电致发光器件作为新一代平板显示技术,在平面显示器以及固体照明等领域展现出广阔的应用前景,从而引起了诸多研究者的关注。芴具有较高的光热稳定性,固态芴的荧光量子效率可达60%-80%,带隙能大于2.90 eV,但是芴具有的刚性平面联苯单元会使材料在发光时容易形成激基缔合物进而产生长波发射,从而影响器件发射光的饱和色纯度以及发光颜色的稳定性。为了改善芴类材料的综合性能,在芴结构上引入基团或侧链可有效降低链间的相互作用,阻止复合物产生,从而达到改善聚芴热稳定性和光谱稳定性的目的。
芴类衍生物具有优异的光电性能、较大的电子离域和较高的荧光量子效率,做为器件时具有明显的电致发光现象,在光电材料领域得到了广泛的应用。芴在结构上具有一定的可修饰性,通过化学方法可以对芴环上2,7,9位上的碳进行结构修饰,本发明在芴环9位上引入不对称结构合成了9-([1,1’-联苯]-3-基)-9-苯基-2-溴芴,有效的降低了材料的空间位阻效应,改善了材料的光电性能。目前9-([1,1’-联苯]-3-基)-9-苯基-2-溴芴及合成方法未见文献报道。
发明内容
本发明的目的在于提供一种新的芴类衍生物9-([1,1’-联苯]-3-基)-9-苯基-2-溴芴及其操作简单、生产成本低、收率高的生产方法。
具体技术方案如下:
本发明所述的9-([1,1’-联苯]-3-基)-9-苯基-2-溴芴的结构式如下:
其合成路线如下:
具体方法如下:
(1)在惰性气体保护下,以甲基四氢呋喃溶液为溶剂, 3-溴联苯与镁粉加热反应,制备3-溴联苯格氏试剂;然后加入2-溴芴酮反应,反应结束后,经水解,分液,分散,干燥得到类白色固体9-([1,1’-联苯]-3-基)-9-羟基-2-溴芴(化合物1)。
(2)将化合物1置于溶剂苯中,控制反应温度和反应时间,加入Zr(SO4)2/ZnO催化,经液相色谱检测无9-([1,1’-联苯]-3-基)-9-羟基-2-溴芴(化合物1)后,通过水洗、过滤除去催化剂、分出有机相、回收苯、甲醇分散,干燥得到目标化合物9-([1,1’-联苯]-3-基)-9-苯基-2-溴芴(化合物2)。
所述的9-([1,1’-联苯]-3-基)-9-羟基-2-溴芴(化合物1)合成过程中,3-溴联苯与2-溴芴酮的摩尔比为1:0.8-1.2,优选1:1.1;反应温度为40 ℃-70 ℃。优选反应温度为70 ℃。
所述的9-([1,1’-联苯]-3-基)-9-苯基-2-溴芴(化合物2)合成过程中,催化剂Zr(SO4)2/ZnO用量为9-([1,1’-联苯]-3-基)-9-羟基-2-溴芴(化合物1)质量的0.1%-1%,优选用量为1%;反应温度为 -20 ℃-0 ℃,反应时间为10 h-24 h。较优选反应温度为 -15 ℃。
本发明使用3-溴联苯作为起始原料反应合成了化合物9-([1,1’-联苯]-3-基)-9-苯基-2-溴芴,生产成本低,操作简单,产品含量大于99.9%,总收率在90%以上,可以满足工业化生产及应用的需求,适合于工业化生产。所得9-([1,1’-联苯]-3-基)-9-苯基-2-溴芴的玻璃化转变温度为176.03 ℃,失重5% 时对应的温度为293.75 ℃,具有优异的热稳定性和较高的熔融温度。9-([1,1’-联苯]-3-基)-9-苯基-2-溴芴内部具有较大的共轭体系和较宽的紫外吸收范围,适用于有机电致发光材料,在有机电致发光材料领域具有潜在的应用前景。
附图说明
图1为本发明化合物9-([1,1’-联苯]-3-基)-9-苯基-2-溴芴的TG曲线;
图2为本发明化合物9-([1,1’-联苯]-3-基)-9-苯基-2-溴芴的DSC曲线。
具体实施方法
为对本发明进行更好地说明,举实例如下:
实例1:
在氩气保护下,向2 L三口烧瓶中加入130.2 g镁粉,加入600 mL甲基四氢呋喃溶液浸没镁粉,然后滴加100 g(0.43 mol)3-溴联苯的甲基四氢呋喃溶液,反应温度控制在50℃,2 h后气相色谱检测3-溴联苯反应完全,将111.4 g 2-溴芴酮固体分批加入,搅拌过夜。反应结束后,加入500 mL水终止反应,分出有机层,无水硫酸钠干燥,抽滤,减压蒸馏回收溶剂,加入500 mL正己烷分散,析出得到白色固体9-([1,1’-联苯]-3-基)-9-羟基-2-溴芴(化合物1)。在2 L三口瓶中,将化合物1溶于500 mL苯中,将反应温度控制到 -10 ℃,加入0.26g Zr(SO4)2/ZnO催化,反应10 h后液相色谱检测无9-([1,1’-联苯]-3-基)-9-羟基-2-溴芴(化合物1)。加入500 mL水终止反应,过滤除去催化剂,分出有机层,减压回收苯,至有固体析出,加入500 mL甲醇分散,过滤得到白色固体9-([1,1’-联苯]-3-基)-9-苯基-2-溴芴(化合物2),干燥后143.9 g,含量99.9%,收率92.1%。
9-([1,1’-联苯]-3-基)-9-苯基-2-溴芴表征数据:
熔点为176.03 ℃;
1H NMR (CDCl3,400 MHz) δ: 7.75(d, J=8.0 Hz, 1H), 7.63(d, J=8.0 Hz,1H), 7.55(d, J=4.0 Hz, 1H), 7.51~7.48(dd, J1=12.0 Hz, J2=8.0 Hz, 1H), 7.46~7.35(m, 8H), 7.32~7.28(m, 3H), 7.27~7.14(m, 5H), 7.12(d, J=4.0 Hz, 1H);
HR-MS (ESI) m/z: Calcd for C31 H21Br {[M + H] + } 474.2788, found474.2795。
实例2:
在氩气保护下,向2 L三口烧瓶中加入117.5 g镁粉,加入700 mL甲基四氢呋喃溶液浸没镁粉,然后滴加130.5 g(0.56 mol)3-溴联苯的甲基四氢呋喃溶液,反应温度控制在60 ℃,2 h后气相色谱检测3-溴联苯反应完全,将159.6 g 2-溴芴酮固体分批加入,搅拌过夜。反应结束后,加入700 mL水终止反应,分出有机层,无水硫酸钠干燥,抽滤,减压蒸馏回收溶剂,加入600 mL正己烷分散,析出得到白色固体9-([1,1’-联苯]-3-基)-9-羟基-2-溴芴(化合物1)。在2 L三口瓶中,将化合物1溶于400 mL苯中,将反应温度控制到 -15 ℃,加入0.56 g Zr(SO4)2/ZnO催化,反应18 h后液相色谱检测无9-([1,1’-联苯]-3-基)-9-羟基-2-溴芴(化合物1)。加入600 mL水终止反应,过滤除去催化剂,分出有机层,减压回收苯,至有固体析出,加入600 mL甲醇分散,过滤得到白色固体9-([1,1’-联苯]-3-基)-9-苯基-2-溴芴(化合物2),干燥后121.4 g,含量99.9%,收率91.2%。
实例3:
在氩气保护下,向2 L三口烧瓶中加入120.1 g镁粉,加入500 mL甲基四氢呋喃溶液浸没镁粉,然后滴加74.6 g(0.32 mol)3-溴联苯的甲基四氢呋喃溶液,反应温度控制在70 ℃,2 h后气相色谱检测3-溴联苯反应完全,将74.6 g 2-溴芴酮固体分批加入,搅拌过夜。反应结束后,加入700 mL水终止反应,分出有机层,无水硫酸钠干燥,抽滤,减压蒸馏回收溶剂,加入700 mL正己烷分散,析出得到白色固体9-([1,1’-联苯]-3-基)-9-羟基-2-溴芴(化合物1)。在2 L三口瓶中,将化合物1溶于600 mL苯中,将反应温度控制到0 ℃,加入1.08 g Zr(SO4)2/ZnO催化,反应23 h后液相色谱检测无9-([1,1’-联苯]-3-基)-9-羟基-2-溴芴(化合物1)。加入700 mL水终止反应,过滤除去催化剂,分出有机层,减压回收苯,至有固体析出,加入700 mL甲醇分散,过滤得到白色固体9-([1,1’-联苯]-3-基)-9-苯基-2-溴芴(化合物2),干燥后115.9 g,含量99.9%,收率92.2%。
Claims (4)
2.合成如权利要求1所述的9-([1,1’-联苯]-3-基)-9-苯基-2-溴芴的方法,其特征在于,通过如下方法实现:
(1)在惰性气体保护下,以甲基四氢呋喃溶液为溶剂, 3-溴联苯与镁粉加热反应,制备3-溴联苯格氏试剂;然后加入2-溴芴酮反应,反应结束后,经水解,分液,分散,干燥得到9-([1,1’-联苯]-3-基)-9-羟基-2-溴芴(化合物1);
(2)将化合物1置于溶剂苯中,控制反应温度和反应时间,加入Zr(SO4)2/ZnO催化,经液相色谱检测无9-([1,1’-联苯]-3-基)-9-羟基-2-溴芴(化合物1)后,通过水洗、过滤除去催化剂、分出有机相、回收苯、甲醇分散,干燥得到目标化合物9-([1,1’-联苯]-3-基)-9-苯基-2-溴芴(化合物2)。
3.如权利要求2所述的9-([1,1’-联苯]-3-基)-9-苯基-2-溴芴的合成方法,其特征在于,步骤(1)中3-溴联苯与2-溴芴酮的摩尔比为1:0.8-1.2,反应温度为40℃-70℃。
4.如权利要求2所述的9-([1,1’-联苯]-3-基)-9-苯基-2-溴芴的合成方法,其特征在于,步骤(2)中催化剂Zr(SO4)2/ZnO用量为9-([1,1’-联苯]-3-基)-9-羟基-2-溴芴(化合物1)质量的0.1%-1%,反应温度为 -20 ℃-0 ℃,反应时间为10 h-24 h。
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