Abstract

Herein, a synthetic approach using selective transition-metal-catalyzed cross-coupling reactions to thermally crosslinkable OLED materials­ based on vinyl-functionalized arylamines is reported. In a modular approach, 9,9-dialkyl-2,7-diiodo-9H-fluorene underwent a selective Ullmann cross-coupling reaction with bromo-substituted-diphenylamines to give 9,9-dialkyl-2,7-bis(bromo-substituted-diphenylamino)-9H-fluorenes that underwent end-functionalization by the Suzuki–Miyaura reaction using potassium vinyltrifluoroborate to give the corresponding 9,9-dialkyl-2,7-bis(vinyl-substituted-diphenylamino)-9H-fluorenes. Novel meta-functionalized materials were synthesized, which are difficult to prepare by traditional synthetic pathways. The thermal behavior of the compounds was investigated by DSC measurements, indicating a lower thermal sensitivity of the meta-substituted materials than their para-functionalized analogues.

Herein, a synthetic approach using selective transition-metal-catalyzed cross-coupling reactions to thermally crosslinkable OLED materials­ based on vinyl-functionalized arylamines is reported. In a modular approach, 9,9-dialkyl-2,7-diiodo-9H-fluorene underwent a selective Ullmann cross-coupling reaction with bromo-substituted-diphenylamines to give 9,9-dialkyl-2,7-bis(bromo-substituted-diphenylamino)-9H-fluorenes that underwent end-functionalization by the Suzuki–Miyaura reaction using potassium vinyltrifluoroborate to give the corresponding 9,9-dialkyl-2,7-bis(vinyl-substituted-diphenylamino)-9H-fluorenes. Novel meta-functionalized materials were synthesized, which are difficult to prepare by traditional synthetic pathways. The thermal behavior of the compounds was investigated by DSC measurements, indicating a lower thermal sensitivity of the meta-substituted materials than their para-functionalized analogues.

中文翻译：

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通过选择性过渡金属催化的交叉偶联反应实现亚功能和对功能化的热可交联OLED材料

摘要

在本文中，报道了使用选择性过渡金属催化的交叉偶联反应与基于乙烯基官能化的芳基胺的可热交联的OLED材料的合成方法。在模块化方法中，将9,9-二烷基-2,7-二碘-9 H-芴与溴取代的二苯胺进行选择性Ullmann交叉偶联反应，得到9,9-二烷基-2,7-双（溴取代的二苯基氨基）-9 ħ通过Suzuki-Miyaura反应使用乙烯基三氟硼酸钾，得到相应的9,9-二烷基-2,7-双（乙烯基取代的二苯基氨基）-9- -fluorenes该后行端官能化ħ -芴。新颖的元合成了功能化的材料，这些材料很难通过传统的合成途径制备。通过DSC测量研究了化合物的热行为，表明间位取代的材料的热敏感性低于对位官能化的类似物。

在本文中，报道了使用选择性过渡金属催化的交叉偶联反应与基于乙烯基官能化的芳基胺的可热交联的OLED材料的合成方法。在模块化方法中，将9,9-二烷基-2,7-二碘-9 H-芴与溴取代的二苯胺进行选择性Ullmann交叉偶联反应，得到9,9-二烷基-2,7-双（溴取代的二苯基氨基）-9 ħ通过Suzuki-Miyaura反应使用乙烯基三氟硼酸钾，得到相应的9,9-二烷基-2,7-双（乙烯基取代的二苯基氨基）-9- -fluorenes该后行端官能化ħ -芴。新颖的元合成了功能化的材料，这些材料很难通过传统的合成途径制备。通过DSC测量研究了化合物的热行为，表明间位取代的材料的热敏感性低于对位官能化的类似物。