Multifunctional modified tert-butyl carbazole phosphine oxide main material and synthesis method and application thereof

A technology of tert-butyl carbazole phosphine and tert-butyl carbazole, which is applied in the field of multifunctional modified tert-butyl carbazole phosphine oxygen host material, synthesis and application, and can solve the problems of high turn-on voltage, luminous efficiency and brightness Low-level problems, to achieve the effects of improving luminous efficiency and brightness, good thermodynamic stability, and enhancing carrier injection and transport capabilities

Active Publication Date: 2014-03-19
HEILONGJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to solve the problem of the low luminous efficiency and brightness of the existing organic electroluminescent host materials applied to organic electroluminescent devices, the high triplet excited state energy level of the host materials and the good carrier injection / transport ability. The problem of high turn-on voltage when it is used as a host material in electroluminescent devices due to the contradiction between them, and provides a multifunctional modified tert-butyl carbazole phosphine oxide host material, synthesis method and application

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  • Multifunctional modified tert-butyl carbazole phosphine oxide main material and synthesis method and application thereof
  • Multifunctional modified tert-butyl carbazole phosphine oxide main material and synthesis method and application thereof
  • Multifunctional modified tert-butyl carbazole phosphine oxide main material and synthesis method and application thereof

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specific Embodiment approach 1

[0067] Specific embodiment 1: The method for synthesizing the multifunctionally modified tert-butyl carbazole phosphine oxide host material of this embodiment is implemented in the following steps:

[0068] 1. Combine 1mmol of carbazole, 2~5mmol of chloro-tert-butane, 50~100ml of chloroform and 0.5~1.5mmol of anhydrous AlCl 3 Stir and react for 5-24 hours, then pour into ice water, and use HCl solution and saturated NaHCO 3 And CH 2 Cl 2 The organic phase is obtained by extraction, and the obtained organic phase is dried and acidified with sulfuric acid, and then saturated NaHCO 3 The organic layer is obtained by extraction, and after drying, a mixed solvent of petroleum ether and ethyl acetate is used as an eluent for purification to obtain tert-butylcarbazole;

[0069] 2. Dissolve the tert-butylcarbazole synthesized in step 1 in N,N-dimethylformamide (DMF), and the molar ratio of tert-butylcarbazole to N-bromosuccinimide is 1: (2~3) Add N-bromosuccinimide (NBS), react for 1~10 hou...

specific Embodiment approach 2

[0073] Embodiment 2: The method for synthesizing the multifunctional modified tert-butyl carbazole phosphine oxide host material of this embodiment is implemented in the following steps:

[0074] 1. Combine 1mmol of carbazole, 2~5mmol of chloro-tert-butane, 50~100ml of chloroform and 0.5~1.5mmol of anhydrous AlCl 3 Stir and react for 5-24 hours, then pour into ice water, and use HCl solution and saturated NaHCO 3 And CH 2 Cl 2 The organic phase is obtained by extraction, and the obtained organic phase is dried and acidified with sulfuric acid, and then saturated NaHCO 3 The organic layer is obtained by extraction, and after drying, a mixed solvent of petroleum ether and ethyl acetate is used as an eluent for purification to obtain tert-butylcarbazole;

[0075] 2. Dissolve the tert-butylcarbazole synthesized in step 1 in N,N-dimethylformamide (DMF), and the molar ratio of tert-butylcarbazole to N-bromosuccinimide is 1: (1~3) Add N-bromosuccinimide (NBS), react for 1~10 hours, pour in...

specific Embodiment approach 3

[0081] Specific embodiment three: This embodiment is different from the specific embodiment two in that the molar ratio of step three is 1:1.5:0.05:5. The bromo-tert-butylcarbazole, anhydrous K 2 CO 3 , CuI and bromobenzene mixed. Other steps and parameters are the same as in the second embodiment.

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Abstract

The invention discloses a multifunctional modified tert-butyl carbazole phosphine oxide main material and a synthesis method and an application thereof, and relates to an organic electroluminescent material and a synthesis method and an application thereof, which are used for solving the problem that the turn-on voltage of an electroluminescent device applied to an organic electroluminescent main material is on the high side. Six kinds of main materials are available; in 2 kinds of main materials, one or two phosphine oxide functional groups with carrier transmission characteristic are introduced to a tert-butyl carbazole parent respectively; and in the other 4 kinds of main materials, one, two or three phosphine oxide functional groups with carrier transmission characteristic are introduced to a 9-phenyl tert-butyl carbazole parent respectively. The tert-butyl carbazole is used as the parent of the main material; since the diphenylphosphine oxide matrix structure has the conjugation breaking effect of the P=O group, the parent has relatively high triple-stage energy level, as well as certain electron injection and transmission capacity, and the luminous efficiency and brightness of a luminous device are improved after the parent is applied to the luminous device; and meanwhile, the turn-on voltage can be reduced to 2.4V.

Description

Technical field [0001] The invention relates to organic electroluminescent materials, synthesis methods and applications. Background technique [0002] 1997 Et al. reported the first organic electro-phosphorescent device using organic transition metal complex as the light-emitting body in "Nature", and found that electro-phosphorescent materials can simultaneously use singlet and triplet excitons to emit light, and its theoretical internal quantum efficiency can reach 100%, aroused widespread attention and research. In recent years, organic electroluminescent diodes (OLEDs) based on phosphorescent materials have attracted attention due to their outstanding advantages such as small size, light weight, flexibility, high luminous efficiency, and fast response speed. However, due to the long excited state lifetime of the electro-phosphorescent material itself, it has serious concentration quenching and triplet-triplet annihilation effects, which greatly reduces the luminous efficie...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/572H01L51/54
Inventor 魏莹许辉杨伟博
Owner HEILONGJIANG UNIV
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