Triarylamine compound, preparation method thereof and organic light-emitting device

A compound, triarylamine technology, applied in the field of organic optoelectronic materials, can solve the problems of low luminous efficiency and service life of organic light-emitting devices, low evaporation temperature, etc., and achieve the effect of improving light extraction efficiency, high purity, and mild conditions

Pending Publication Date: 2021-12-21
CHANGCHUN HYPERIONS TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at present, the vapor deposition temperature of organic covering layer materials in OLEDs is low, and the luminous efficiency and service life of organic light-emitting devices are low. Therefore, it is imminent to develop new covering layer materials to improve the luminous efficiency and service life of organic light-emitting devices. matter

Method used

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  • Triarylamine compound, preparation method thereof and organic light-emitting device
  • Triarylamine compound, preparation method thereof and organic light-emitting device
  • Triarylamine compound, preparation method thereof and organic light-emitting device

Examples

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Effect test

preparation example Construction

[0159] The present invention also provides a kind of preparation method of triarylamine compound, described comprises the following steps:

[0160] S1. Under a nitrogen atmosphere, under the action of a palladium catalyst and a base, the primary amine compound a and the intermediate M are subjected to a coupling reaction to obtain the crude intermediate A;

[0161] S2. The crude intermediate A is recrystallized to obtain a purified intermediate A;

[0162] S3. Under nitrogen atmosphere, under the action of palladium catalyst and alkali, the purified intermediate A and the halogen compound c undergo a coupling reaction to obtain the crude compound of formula I, with an HPLC purity of 85% to 95%;

[0163] S4. The crude compound of formula I is subjected to column chromatography and recrystallization to obtain a semi-finished triarylamine compound, and the HPLC purity is greater than or equal to 99%;

[0164] S5. The semi-finished triarylamine compound is sublimated to obtain a ...

Embodiment 1

[0306] [Example 1] Synthesis of compound 4

[0307]

[0308] Synthesis of Intermediate A-1

[0309] Under the protection of nitrogen, toluene (600mL), a-1 (8.46g, 50mmol), M-1 (23.87g, 50mmol), palladium acetate (0.15g, 0.60mmol), tert-butanol were added successively to the 1L reaction flask Sodium (7.69 g, 80 mmol) and tri-tert-butylphosphine (6 mL in toluene). And react under the condition of reflux for 2.5 hours. After the reaction was stopped, the mixture was cooled to room temperature, filtered with diatomaceous earth, the filtrate was concentrated, the residue was recrystallized with toluene, filtered with suction and rinsed with toluene to obtain a recrystallized solid to obtain intermediate A-1 (21.78g, yield 80 %), HPLC detection solid purity >= 99.55%.

[0310] Synthesis of compound 4

[0311] Under nitrogen protection, add toluene solvent (500mL), c-1 (9.56g, 35mmol), intermediate A-1 (19.80g, 35mmol), Pd 2 (dba) 3 (0.41g, 0.45mmol), BINAP (0.37g, 0.60mmol)...

Embodiment 2

[0312] [Example 2] Synthesis of compound 17

[0313]

[0314] Using the same method as in Synthesis Example 1, replace a-1 with equimolar a-2, replace M-1 with equimolar M-2, replace c-1 with equimolar c-2, and synthesize compound 17 (20.03g ), HPLC detection solid purity >= 99.97%. Mass Spectrum m / z: 762.4038 (Theoretical: 762.4022). Theoretical element content (%)C 58 h 42 D. 5 N: C, 91.30; H, 6.87; N, 1.84. Measured element content (%): C, 91.34; H, 6.83; N, 1.80.

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Abstract

The invention provides a triarylamine compound, a preparation method thereof and an organic light-emitting device, which relate to the technical field of organic photoelectric materials. The triarylamine compound has an aliphatic ring on benzene or 9-phenyl of fluorenyl, the aliphatic ring has electron donating ability relative to aryl, the electron donating ability of the compound is further enhanced, and the triarylamine compound has excellent steric configuration, effectively controls the crystallinity of a material, and has good thermal stability. The light-emitting efficiency and the service life of the organic light-emitting device can be improved; the driving voltage of the device is reduced; and the triarylamine compound provided by the invention is applied to the organic light-emitting device as a covering layer material, so that the light-emitting efficiency of the organic light-emitting device can be improved, and meanwhile, the service life of the device can also be prolonged. The triarylamine compound is simple to synthesize and easy to operate, and can be widely applied to the fields of panel display, lighting sources, organic solar cells, organic photoreceptors or organic thin film transistors and the like.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a triarylamine compound, a preparation method thereof, and an organic light-emitting device. Background technique [0002] Organic light-emitting diodes (Organic Light-Emitting Diodes, OLEDs) are also called organic light-emitting semiconductors. OLED display technology has a series of advantages such as self-illumination, low-voltage DC drive, full curing, wide viewing angle, light weight, simple composition and process. , and its response speed can reach 1000 times that of liquid crystal displays. Therefore, organic light-emitting devices have broad application prospects, and the development of suitable organic thin film materials has always been the research focus of the OLED industry. [0003] Thin film materials generally used in OLEDs include light emitting materials, auxiliary materials and electrode materials. The auxiliary materials mainly inclu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/61C07D209/80C07D209/86C07D209/88C07D219/08C07D221/20C07D263/57C07D263/60C07D265/38C07D307/77C07D307/91C07D311/82C07D311/90C07D333/50C07D333/76C07D335/04C07D335/20C07D405/12C07D409/12C07D413/12C07D417/12H01L51/54H01L51/50
CPCC07C211/61C07D307/91C07D307/77C07D333/76C07D333/50C07D209/88C07D209/86C07D335/04C07D409/12C07D311/90C07D335/20C07D311/82C07D219/08C07D265/38C07D417/12C07D263/57C07D263/60C07D413/12C07D209/80C07D405/12C07D221/20C07C2602/08C07C2603/18C07C2602/28C07C2603/94C07C2603/70C07C2603/40C07C2603/52C07B2200/05H10K85/622H10K85/623H10K85/624H10K85/625H10K85/626H10K85/636H10K85/633H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K50/15Y02E10/549
Inventor 韩春雪刘喜庆陆影周雯庭
Owner CHANGCHUN HYPERIONS TECH CO LTD
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