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Screw-ring hole-transporting material, and preparation method and application thereof

A technology of hole transport materials and spiro rings, which is applied in the direction of luminescent materials, carboxylic acid nitrile preparation, amino compound preparation, etc. It can solve the problems of blocking the full practical application of OLED technology, limiting the luminous efficiency, service life and operating voltage of devices, etc.

Active Publication Date: 2017-06-23
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Electron transport materials and hole injection materials or hole transport materials are major obstacles to the full practical application of OLED technology, which directly limit the luminous efficiency, service life and operating voltage of the device.

Method used

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  • Screw-ring hole-transporting material, and preparation method and application thereof
  • Screw-ring hole-transporting material, and preparation method and application thereof
  • Screw-ring hole-transporting material, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] The preparation of embodiment 1 compound 1

[0058] (1) Preparation of Compound II:

[0059]

[0060] Get raw material 23.1g 1-bromoacenaphthylene (100.0mmol), 14.7g potassium acetate (150mmol) 30.5 double pinacol borate (120mmol) and join in 250g toluene, under the protection of nitrogen, add catalyst 0.8g Pd (dppf)Cl 2 (1mmol), then be heated to reflux, select water separator to divide water in the reaction process, adopt thin-layer chromatography (TLC) to track the reaction process simultaneously, after about 5.0 hour reaction finishes, add 200g water, system layering, then wash with water Finally, the organic phase was dried over anhydrous sodium sulfate, and then purified by column chromatography with toluene to obtain 23.1 g of compound II with a yield of 83.01%.

[0061] (2) Preparation of Compound IV:

[0062]

[0063] Get the compound compound II (12.5g, 45.0mmol), m-bromoiodobenzene (15.3g, 54.0mmol), 12.4g potassium carbonate (90mmol), 50g water and ...

Embodiment 2

[0073] The preparation of embodiment 2 compound 15

[0074] (1) Preparation of Compound IV:

[0075]

[0076] Take the obtained compound II (12.5g, 45.0mmol), 2-bromo-3-iodonaphthalene (16.6g, 50.0mmol), 12.4g potassium carbonate (90mmol), 50g water and 140g toluene, under the protection of nitrogen, Add catalyst 0.5g Pd(PPh 3 ) 4 (0.45mmol), then heated to reflux, while adopting thin-layer chromatography (TLC) to track the reaction process, after about 12.0 hours of reaction, after being down to room temperature, the system was layered, and after washing with water, the organic phase was decompressed and decompressed. Solvent until there is no distillate, and then recrystallize from toluene ethanol to obtain 13.0 g of compound IV with a yield of 81.25%.

[0077] (2) Preparation of compound VI:

[0078]

[0079] Compound IV (12.5 g, 35.0 mmol) obtained in step (1) was added to 100 g of THF solution, under the protection of nitrogen, the temperature was lowered to -78...

Embodiment 3

[0086] The preparation of embodiment 3 compound 16

[0087] (1) Preparation of Compound IV:

[0088]

[0089] Take the obtained compound II (12.5g, 45.0mmol), 1-bromo-2-iodonaphthalene (16.6g, 50.0mmol), 12.4g potassium carbonate (90mmol), 50g water and 140g toluene, under the protection of nitrogen, Add catalyst 0.5g Pd(PPh 3 ) 4 (0.45mmol), then heated to reflux, while adopting thin-layer chromatography (TLC) to track the reaction process, after about 12.0 hours of reaction, after being down to room temperature, the system was layered, and after washing with water, the organic phase was decompressed and decompressed. Solvent until there is no distillate, and then recrystallize with toluene ethanol to obtain 12.2 g of compound IV with a yield of 76.25%.

[0090] (2) Preparation of compound VI:

[0091]

[0092] Compound IV (12.5 g, 35.0 mmol) obtained in step (1) was added to 100 g of THF solution, under the protection of nitrogen, the temperature was lowered to -78...

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Abstract

The invention belongs to the technical field of screw-ring hole-transporting materials, and in particular relates to a screw-ring hole-transporting material, and a preparation method and application thereof. The screw-ring hole-transporting material has the following structural general formula: FORMULA, where R1 is selected from one of a hydrogen group, a halogen group, a cyano group, C1-10 alkyl, and substituted or unsubstituted C1-12 alkoxy; A is phenylene or naphthylene; R2 and R3 are independently selected from one of phenyl, C7-14 benzene alkyl, C10-60 polycyclic conjugate aryl, and C12-60 aromatic heterocyclic groups containing at least one of N, S and O. The screw-ring hole-transporting material is used for preparing a hole-transporting layer material of an OLED device. The material has excellent heat stability, the glass-transition temperature and the dissolution temperature are high, a good amorphous thin film is easily formed, the material is applied to an electroluminescent device, and a more stable effect and a longer service life can be obtained.

Description

technical field [0001] The invention belongs to the technical field of spiro-ring hole transport materials, in particular to a spiro-ring hole transport material and its preparation method and application. Background technique [0002] The research on spiro-ring hole transport devices started in the 1960s, and it was not until the end of the 1980s that OLEDs flourished. OLED has the advantages of full solid-state, low-voltage drive, active light emission, fast response, wide viewing angle, large light-emitting area, light-emitting wavelength covering the entire visible light region, and rich colors. It has great advantages in the field of full-color large-area display and has become an extremely Flat panel display devices in the foreground. The luminous brightness of a spiro-ring hole transport device is proportional to the product of the concentration of holes and electrons and the recombination probability of excitons. To obtain higher luminous efficiency, not only holes ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C255/58C07C209/10C07C211/56C07C211/54C07C211/60C07C213/02C07C217/80C07D209/86C07D209/88C07D307/91C07D333/76C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07C211/54C07C211/56C07C211/60C07C217/80C07C255/58C07D209/86C07D209/88C07D307/91C07D333/76C09K2211/1088C09K2211/1092C09K2211/1014C09K2211/1029H10K85/636H10K85/633H10K85/631H10K85/6576H10K85/6574H10K85/6572H10K50/15H10K50/11
Inventor 慈振华林存生石宇付文岗孙晟源胡葆华孟凡民马永洁
Owner VALIANT CO LTD
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