Organic semiconductor material, preparation method thereof, and electroluminescent device

Abstract

The invention provides an organic semiconductor material with a chemical formula shown below. The organic semiconductor material provided by the invention has relatively high triplet state energy level, such that energy is effectively prevented from being transported back to the main material during a luminescent process, and luminescent efficiency is greatly improved. The material also has relatively high thermal stability. The invention also provides a preparation method of the organic semiconductor material, and an electroluminescent device comprising the organic semiconductor material.

Description

technical field

[0001] The invention belongs to the field of photoelectric materials, and in particular relates to an organic semiconductor material, a preparation method and an electroluminescence device. Background technique

[0002] Organic electroluminescent devices have the advantages of low driving voltage, fast response speed, wide viewing angle range, rich colors through fine-tuning of chemical structure, easy realization of high resolution, light weight, and large-area flat-panel display. 21st Century Flat Panel Display Technology" has become a research hotspot in the fields of materials, information, physics and flat panel display. Future efficient commercial OLEDs will likely contain organometallic phosphors because they can trap both singlet and triplet excitons, thereby achieving 100% internal quantum efficiency. However, due to the relatively long lifetime of excited-state excitons in transition metal complexes, the unwanted triplet-triplet (T 1 -T 1 ) are q...

Examples

preparation example Construction

[0025] The invention provides a kind of preparation method of organic semiconductor material, comprises the steps:

[0026] Provides compound A: and compound B: Under an inert atmosphere, first dissolve compound A in an organic solvent, then add compound B, an inorganic base and a catalyst to the organic solvent containing compound A and react at 70-120°C for 3-12 hours, the compound A The molar ratio with compound B is 1:1~1:1.2, and the chemical formula of the organic semiconductor material obtained by stopping the reaction is as follows:

[0027]

[0028] The preparation method of the organic semiconductor material further includes a post-processing step. The post-processing step specifically includes: using n-hexane as eluent to separate and purify the organic semiconductor material obtained by stopping the reaction through a silica gel layer, and vacuum drying to obtain the target product.

[0029] The condition of the vacuum drying is drying at 50-70° C. for 12-24...

Embodiment 1

[0040] The preparation process of 2-(3-(9H-carbazol-9-yl)phenyl)-1-phenyl-1H-phenanthrene[9,10-d]imidazole The preparation steps are as follows:

[0041]

[0042] Under nitrogen protection, 2-(3-bromophenyl)-1-phenyl-1H-phenanthrene[9,10-d]imidazole (38g, 80mmol) was dissolved in 200mLN,N-dimethylformamide ( DMF) solution, then added 9H-carbazole (13.4g, 80mmol), potassium carbonate (22.1g, 160mmol) and cuprous iodide (1.52g, 8mmol). The reactants were stirred and reacted at 120° C. for 6 hours. Stop the reaction and cool to room temperature, filter, and wash the solid three times with distilled water to obtain the product 2-(3-(9H-carbazol-9-yl)phenyl)-1-phenyl-1H-phenanthrene[9,10-d ] imidazole, and then use the eluent n-hexane to separate by silica gel column chromatography, and then dry under vacuum at 50°C for 24h to obtain an off-white solid. The yield was 81%.

[0043] Experimental test data: mass spectrum: m / z535.2 (M + +1); elemental analysis (%) C 39 h 25 N ...

Embodiment 2

[0047] The preparation process of 2-(3-(9H-carbazol-9-yl)phenyl)-1-phenyl-1H-phenanthrene[9,10-d]imidazole The preparation steps are as follows:

[0048]

[0049] Under nitrogen protection, 2-(3-bromophenyl)-1-phenyl-1H-phenanthrene[9,10-d]imidazole (38g, 80mmol) was dissolved in 200mL toluene (Tol) solution, and then added 9H-carbazole (14.7g, 88mmol), cesium carbonate (57.2g, 176mmol), copper powder (0.768g, 12mmol). The reactants were stirred and reacted at 110° C. for 9 hours. Stop the reaction and cool to room temperature, filter, and wash the solid three times with distilled water to obtain the product 2-(3-(9H-carbazol-9-yl)phenyl)-1-phenyl-1H-phenanthrene[9,10-d ] imidazole, and then use the eluent n-hexane to separate by silica gel column chromatography, and then dry under vacuum at 50°C for 24h to obtain an off-white solid. The yield was 84%.

technical field

[0001] The invention belongs to the field of photoelectric materials, and in particular relates to an organic semiconductor material, a preparation method and an electroluminescence device. Background technique

[0002] Organic electroluminescent devices have the advantages of low driving voltage, fast response speed, wide viewing angle range, rich colors through fine-tuning of chemical structure, easy realization of high resolution, light weight, and large-area flat-panel display. 21st Century Flat Panel Display Technology" has become a research hotspot in the fields of materials, information, physics and flat panel display. Future efficient commercial OLEDs will likely contain organometallic phosphors because they can trap both singlet and triplet excitons, thereby achieving 100% internal quantum efficiency. However, due to the relatively long lifetime of excited-state excitons in transition metal complexes, the unwanted triplet-triplet (T 1 -T 1 ) are q...

Examples

preparation example Construction

[0025] The invention provides a kind of preparation method of organic semiconductor material, comprises the steps:

[0026] Provides compound A: and compound B: Under an inert atmosphere, first dissolve compound A in an organic solvent, then add compound B, an inorganic base and a catalyst to the organic solvent containing compound A and react at 70-120°C for 3-12 hours, the compound A The molar ratio with compound B is 1:1~1:1.2, and the chemical formula of the organic semiconductor material obtained by stopping the reaction is as follows:

[0027]

[0028] The preparation method of the organic semiconductor material further includes a post-processing step. The post-processing step specifically includes: using n-hexane as eluent to separate and purify the organic semiconductor material obtained by stopping the reaction through a silica gel layer, and vacuum drying to obtain the target product.

[0029] The condition of the vacuum drying is drying at 50-70° C. for 12-24...

Embodiment 1

[0040] The preparation process of 2-(3-(9H-carbazol-9-yl)phenyl)-1-phenyl-1H-phenanthrene[9,10-d]imidazole The preparation steps are as follows:

[0041]

[0042] Under nitrogen protection, 2-(3-bromophenyl)-1-phenyl-1H-phenanthrene[9,10-d]imidazole (38g, 80mmol) was dissolved in 200mLN,N-dimethylformamide ( DMF) solution, then added 9H-carbazole (13.4g, 80mmol), potassium carbonate (22.1g, 160mmol) and cuprous iodide (1.52g, 8mmol). The reactants were stirred and reacted at 120° C. for 6 hours. Stop the reaction and cool to room temperature, filter, and wash the solid three times with distilled water to obtain the product 2-(3-(9H-carbazol-9-yl)phenyl)-1-phenyl-1H-phenanthrene[9,10-d ] imidazole, and then use the eluent n-hexane to separate by silica gel column chromatography, and then dry under vacuum at 50°C for 24h to obtain an off-white solid. The yield was 81%.

[0043] Experimental test data: mass spectrum: m / z535.2 (M + +1); elemental analysis (%) C 39 h 25 N ...

Embodiment 2

[0047] The preparation process of 2-(3-(9H-carbazol-9-yl)phenyl)-1-phenyl-1H-phenanthrene[9,10-d]imidazole The preparation steps are as follows:

[0048]

[0049] Under nitrogen protection, 2-(3-bromophenyl)-1-phenyl-1H-phenanthrene[9,10-d]imidazole (38g, 80mmol) was dissolved in 200mL toluene (Tol) solution, and then added 9H-carbazole (14.7g, 88mmol), cesium carbonate (57.2g, 176mmol), copper powder (0.768g, 12mmol). The reactants were stirred and reacted at 110° C. for 9 hours. Stop the reaction and cool to room temperature, filter, and wash the solid three times with distilled water to obtain the product 2-(3-(9H-carbazol-9-yl)phenyl)-1-phenyl-1H-phenanthrene[9,10-d ] imidazole, and then use the eluent n-hexane to separate by silica gel column chromatography, and then dry under vacuum at 50°C for 24h to obtain an off-white solid. The yield was 84%.

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