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Diazcarbazole derivative, preparation method thereof, and application of diazcarbazole derivative as electroluminescent material

An azacarbazole and derivative technology, applied in the application field of organic optoelectronic materials, can solve problems such as low luminous efficiency, and achieve the effect of good carrier migration characteristics

Inactive Publication Date: 2019-03-05
WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] As early as the beginning of the 20th century, people discovered the phenomenon of organic electroluminescence. In 1963, Pope et al. reported the electroluminescent device of single crystal anthracene for the first time, but the thickness of the single crystal was 20 μm, and the driving voltage was as high as 400V. The efficiency is extremely low, and compared with the vigorous development of inorganic material devices at that time, it has not received more attention

Method used

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  • Diazcarbazole derivative, preparation method thereof, and application of diazcarbazole derivative as electroluminescent material
  • Diazcarbazole derivative, preparation method thereof, and application of diazcarbazole derivative as electroluminescent material
  • Diazcarbazole derivative, preparation method thereof, and application of diazcarbazole derivative as electroluminescent material

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0111] Embodiment 1, the preparation of compound 1

[0112]

[0113] Add 3-chloro-2-nitropyridine (5g, 31.63mmol), 3-pyridineboronic acid (3g, 37.75mmol) into a 500ml single-necked flask, dissolve 50ml of 2M aqueous potassium carbonate in 50ml of ethanol, and dissolve in a solvent of 100ml of toluene . in N 2 Under the protection conditions, adding PdCl 2 (PPh 3 ) 2 (0.75 g, 0.98 mmol). The temperature was raised slowly to 100°C, and the mixture was reacted under reflux for 24h. After cooling, the liquid was separated, the organic layer was rotary evaporated, and the column was passed through petroleum ether and ethyl acetate (1.5:1) to obtain 4.5 g of a light yellow solid with a yield of 65%. MS(APCI)m / z calcd for C 10 h 7 N 3 o 2 :201.20,found[M + ]:201.89.

Embodiment 2

[0114] Embodiment 2, the preparation of compound 2

[0115]

[0116] Add 3-(2-nitropyridin-3-yl)pyridine (4.06g, 20.25mmol) and triphenylphosphine (13.3g, 50.65mmol) solvent in 100ml o-dichlorobenzene solvent in a single-necked flask of 250ml . in N 2Under the condition of protection, the temperature was raised to 180°C, and the reaction was refluxed for 24h. After the reaction was completed, distill under reduced pressure, concentrate the reaction solvent to 40ml, and pass through the column with dichloromethane and methanol (15:1) to obtain 2g of white solid with a yield of 60%. MS(APCI)m / z calcd for C 10 h 7 N 3 : 169.20, Found[M + ]:169.69.

Embodiment 3

[0117] Embodiment 3, the preparation of compound 3

[0118]

[0119] Add compound 2 (1g, 6mmol) in the single-necked flask of 250ml, o-bromoiodobenzene (2g, 7.2mmol), copper powder (1.2g, 18mmol), K 2 CO 3 (2.5g, 18mmol) was dissolved in 100ml of dry DMF solvent. in N 2 Under the conditions of protection, the temperature was raised to 150°C, and the reaction was carried out for 48h. After the reaction was terminated, it was cooled to room temperature, extracted, spin-dried, and passed through the column to obtain a light yellow liquid with a yield of 70%. MS(APCI) m / z calcd for C 16 h 10 BrN 3 : 323.00, Found[M + ]:324.04.

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Abstract

The invention belongs to the technical field of organic photoelectric material application, and particularly relates to a diazcarbazole derivative with different relative positions of N atoms and an application of the diazcarbazole derivative as an electroluminescent material. Carbazole-like group diazcarbazole with an electron-deficient property is introduced, and a triplet state of the materialcan be realized and the molecular orbital energy level can be adjustable through bonding with different groups, so that efficient recombination of carriers in an organic electroluminescent device is achieved fundamentally, an efficient and energy-saving organic light emitting diode (OLED) device is obtained, and the diazcarbazole derivative can be widely applied to the field of organic electroluminescence. The structural general formula of the material is as shown in the formula I, wherein a same diazcarbazole (diazcarbazole with N positions of 1,8, 1,7, 1,6, 2,7, 2,6, 2,5, 3,6, 3,5, and 4,5)is taken as a core, the L group is a bridging group for bonding the diazlocarbazole, the L group is selected from aromatic groups or aromatic heterocyclic groups containing heteroatoms, m and n are the numbers of the diazicarbazole, and the sum of m and n is greater than or equal to 1.

Description

technical field [0001] The invention belongs to the technical field of application of organic photoelectric materials, and in particular relates to bisazacarbazole derivatives with different relative positions of N atoms, a preparation method thereof, and an application as an electroluminescent material. Background technique [0002] In recent years, organic light emitting diode (OLED) has become a very popular emerging flat panel display industry in the world, mainly because OLED displays have self-illumination, wide viewing angle, rich colors, fast response time, low power consumption, and luminous efficiency. High, low operating voltage, good temperature characteristics, wide range of material selection, thin panel thickness, large-size and flexible panels can be produced, and simple manufacturing process, and has the potential for low cost. It is known as the next-generation "star" flat panel display technology . [0003] The luminescence of OLED belongs to electrolumin...

Claims

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Application Information

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IPC IPC(8): C07D471/14C07D519/00C07F7/08C09K11/06H01L51/54
CPCC09K11/06C07D471/14C07D519/00C07F7/0812C09K2211/1029C09K2211/1059C09K2211/1044C09K2211/1033C09K2211/1037C09K2211/1088C09K2211/1092H10K85/631H10K85/654H10K85/6576H10K85/6574H10K85/657H10K85/40H10K85/6572
Inventor 穆广园庄少卿叶少峰
Owner WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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