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1,3-biscarbazolyl benzene type phosphorescent host material, and synthesis method and application thereof

A technology based on dicarbazole benzenes and phosphorescent main body, applied in the application field of optoelectronic materials, which can solve the problems of hindering widespread use, low material stability, high efficiency roll-off, etc.

Pending Publication Date: 2019-11-12
镇江博润新材料有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The main technical problem to be solved by the present invention is that the glass transition temperature of commonly used blue phosphorescent main materials is low, the stability of the material itself is not high, and it has high efficiency roll-off under high brightness, which hinders its widespread use, and provides a 1 , 3-dicarbazole benzene-based phosphorescent host material, its synthesis method and its application

Method used

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  • 1,3-biscarbazolyl benzene type phosphorescent host material, and synthesis method and application thereof
  • 1,3-biscarbazolyl benzene type phosphorescent host material, and synthesis method and application thereof
  • 1,3-biscarbazolyl benzene type phosphorescent host material, and synthesis method and application thereof

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preparation example Construction

[0060] The synthesis method of the 1,3-dicarbazole benzene phosphorescent host material disclosed by the present invention comprises the following steps:

[0061] Step 1: Dissolve m-dibromobenzene and carbazole in DMPU (1,3-dimethylpropylene urea), heat to 180°C for reflux for 48 hours, and use Ullmann reaction to obtain mCP (1,3-dicarboxylate azoles);

[0062] Step 2: Dissolving NBS (N,N'-dimethylbenzamide) and mCP in DMF and reacting at room temperature for 6 hours to obtain 3-bromo-1,3-dicarbazolylbenzene;

[0063] Step 3: Dissolving 3-bromo-1,3-dicarbazolylbenzene and diboronic acid ester in THF (tetrahydrofuran) and refluxing for 24 hours to form 3-boronic acid ester-1,3-dicarbazolylbenzene;

[0064] Step 4: using the Suzuki reaction to obtain 3-phenyl-1,3-dicarbazolylbenzene substituted by o-, m-, and p-bromine;

[0065] Step 5: Ullmann reaction, Suzuki reaction or diphenylphosphine-oxygen reaction are used to form the host luminescent material substituted by ortho-, m...

Embodiment 1

[0073] Embodiment 1: when R in formula I 1 For diphenylphosphoryloxy, R 2 , R 3 , R 4 and R 5 When it is a hydrogen group, it is named 3-(2-diphenylphosphoryloxy)phenyl-1,3-dicarbazolylbenzene (2-(9-(3-(9H-carbazol-9-yl)phenyl)- The structural formulas of 9H-carbazol-3-yl)phenyl)diphen-ylp hosphine oxide (mCPoPO) are as follows:

[0074]

[0075] The mCPoPO of the present invention can be synthesized by the following method.

[0076] Step a: Dissolve 1 mol of m-dibromobenzene and 2.5 mol of carbazole in 250 mL of DMPU (1,3-dimethylpropylene urea), heat to 180°C for reflux for 48 hours, and use the Ullmann reaction to obtain 0.94 mol of mCP ( 1,3-dicarbazole benzene);

[0077] Step b: Dissolve 0.9mol NBS (N,N'-dimethylbenzamide) and 0.92mCP in DMF and react at room temperature for 6h to obtain 0.89mol 3-bromo-1,3-dicarbazolylbenzene ;

[0078] Step c: Dissolve 0.85mol 3-bromo-1,3-dicarbazolylbenzene and 1.0mol diboronic ester in 1LTHF (tetrahydrofuran) and reflux for...

Embodiment 2

[0082] Embodiment 2: when R in formula I 2 For diphenylphosphoryloxy, R 1 , R 3 , R 4 and R 5 When it is a hydrogen group, it is named 3-(3-diphenylphosphoryloxy)phenyl-1,3-dicarbazolylbenzene (3-(9-(3-(9H-carbazol-9-yl)phenyl) -9H-carbazol-3-yl)phenyl)diphenylph osphine oxide (mCPmPO), its structural formula is as follows:

[0083]

[0084] The mCPmPO of the present invention can be synthesized by the following method.

[0085] Step a: Dissolve 1 mol of dibromobenzene and 2.5 mol of carbazole in 250 mL of DMPU (1,3-dimethylpropylene urea), heat to 180°C for reflux for 48 hours, and use the Ullmann reaction to obtain 0.94 mol of mCP ( 1,3-dicarbazole benzene);

[0086] Step b: Dissolve 0.9mol NBS (N,N'-dimethylbenzamide) and 0.92mCP in DMF and react at room temperature for 6h to obtain 0.89mol 3-bromo-1,3-dicarbazolylbenzene ;

[0087] Step c: Dissolve 0.85mol 3-bromo-1,3-dicarbazolylbenzene and 1.0mol diboronic ester in 1LTHF (tetrahydrofuran) and reflux for 24h to f...

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Abstract

The invention discloses a 1,3-biscarbazolyl benzene type phosphorescent host material, and a synthesis method and application thereof, and belongs to the technical field of optoelectronic material application. The blue phosphorescent host material adopting N,N'-biscarbazolyl-1,3-benzene as a fixed structural unit is synthesized through a simple synthesis route, has a relatively high glass transition temperature, good hole and electron transporting capability, good film forming performance, stable properties, a device efficiency of greater than 40 Cd / A and low roll-off efficiency in high brightness, and is an ideal high-efficiency blue phosphorescent bipolar host material. Through the 1,3-biscarbazolyl benzene type phosphorescent host material, a problem that common blue phosphorescent hostmaterials cannot be widely applied due to low glass transition temperatures, poor stability, and high roll-off efficiency at high brightness is solved.

Description

technical field [0001] The invention belongs to the field of photoelectric material application science and technology, and specifically relates to a 1,3-dicarbazole benzene phosphorescent host material, a synthesis method and an application thereof. [0002] technical background [0003] Since the first discovery of organic anthracene crystals emitting light under high driving voltage in 1963, the phenomenon of organic electroluminescence has attracted great attention from scientists. In 1987, Deng Qingyun's research group proposed for the first time the OLED structure using an organic multilayer amorphous film to reduce the driving voltage and increase the luminous intensity; in 1990, Burroughes et al. reported the polymer light-emitting diode for the first time. Since then, organic electroluminescence research has entered the A whole new stage. [0004] Most of the current phosphorescent electroluminescent devices adopt the host-guest structure, that is, the phosphorescen...

Claims

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Application Information

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IPC IPC(8): C07D401/14C07D403/14C07F9/572C09K11/06H01L51/54
CPCC07F9/5728C07D403/14C07D401/14C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1044H10K85/654H10K85/6572
Inventor 杨宏训张建资徐明航
Owner 镇江博润新材料有限公司
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