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Novel organic electroluminescent compounds and organic electroluminescent device comprising the same

A compound and luminescent technology, applied in electroluminescence light sources, organic chemistry, electric solid-state devices, etc., can solve the problems of unsatisfactory working life and luminous efficiency, low glass transition temperature, and degradation of organic EL devices , to achieve the effect of excellent hole transport ability, high luminous efficiency and long driving life

Inactive Publication Date: 2015-01-07
ROHM & HAAS ELECTRONICS MATERIALS LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although these phosphorescent host materials provide good luminescence characteristics, they have the following disadvantages: (1) They may degrade during high temperature deposition in vacuum due to their low glass transition temperature and poor thermal stability
Therefore, EL devices using conventional phosphorescent materials have no advantage in power efficiency (lm / W)
(3) In addition, the working life and luminous efficiency of organic EL devices are not satisfactory
[0009] However, organic EL devices containing the disclosed compounds are unsatisfactory in terms of power efficiency, luminous efficiency, quantum efficiency and operating life

Method used

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  • Novel organic electroluminescent compounds and organic electroluminescent device comprising the same
  • Novel organic electroluminescent compounds and organic electroluminescent device comprising the same
  • Novel organic electroluminescent compounds and organic electroluminescent device comprising the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0103] Embodiment 1: the preparation of compound C-1

[0104]

[0105] Preparation of compound C-1-1

[0106] 2-Bromo-7-iodo-9,9-dimethyl-9H-fluorene (25.0 g, 62.6 mmol), 9-phenyl-9H-carbazol-3-ylboronic acid (16.3 g, 56.9 mmol ), tetrakis(triphenylphosphine)palladium(O)[Pd(PPh 3 ) 4 ] (3.6g, 3.1mmol) and Na 2 CO 3 (19.9g, 216.0 mmol) was added to the flask and after dissolving the reaction mixture by adding toluene (400.0ml), ethanol (EtOH) (100.0ml) and distilled water (100.0ml), the reaction mixture was heated at 120°C Stir for 3 hours. After the reaction, the reaction was terminated by slowly adding distilled water, and the organic layer was extracted with vinyl acetate (EA). with MgSO 4 The obtained organic layer was dried to remove residual moisture, and separated by column chromatography to obtain compound C-1-1 (27.5 g, 53.5 mmol, yield: 84%).

[0107] Preparation of compound C-1-2

[0108] Add compound C-1-1 (27.5g, 53.5mmol), 2-chloroaniline (11.2ml,...

Embodiment 2

[0113] Embodiment 2: the preparation of compound C-22

[0114]

[0115] Preparation of Compound C-22-1

[0116] 1,3-Dibromobenzene and sulfuric acid (250.0 ml) were added to the flask and the reaction mixture was cooled to an internal temperature of 0°C. Nitric acid (28.6ml) was slowly added to the flask and the reaction mixture was stirred for 30 minutes. After the reaction was completed, ice water was added to the reaction mixture, and the obtained solid was filtered and rinsed with water. The solid was rinsed with NaOH to make a neutral solid. The solid was separated by column chromatography to obtain compound C-22-1 (60.0 g, 213.5 mmol, yield: 50%).

[0117] Preparation of compound C-22-2

[0118] Compound C-22-1 (60.0g, 213.5 mmol), dibenzo[b, d]thiophen-4-ylboronic acid (40.6g, 177.9 mmol), Pd(PPh 3 ) 4 (8.2g, 7.1mmol) and Na 2 CO 3 (56.6 g, 534.0 mmol) was added to the flask and after dissolving the reaction mixture by adding toluene (520.0 ml), EtOH (2...

Embodiment 3

[0125] Embodiment 3: the preparation of compound C-26

[0126]

[0127] Preparation of compound C-26-1

[0128] Compound C-22-1 (60.0g, 213.5 mmol), dibenzo[b, d]furan-4-ylboronic acid (37.7g, 177.9 mmol), Pd(PPh 3 ) 4 (10.2g, 8.8mmol) and Na 2 CO 3 (56.6 g, 534.0 mmol) was added to the flask and after dissolving the reaction mixture by adding toluene (520.0 ml), EtOH (260.0 ml) and distilled water (260.0 ml), the reaction mixture was stirred at 120° C. for 3 hours . After the reaction, the reaction was completed by slowly adding distilled water, and the organic layer was extracted with EA. with MgSO 4 The obtained organic layer was dried to remove residual moisture, and separated by column chromatography to obtain compound C-26-1 (42.0 g, 114.0 mmol, yield: 54%).

[0129] Preparation of compound C-26-2

[0130] Compound C-26-1 (10.0g, 29.7mmol), 9-phenyl-9H-carbazol-3-ylboronic acid (10.2g, 35.7mmol), Pd(PPh 3 ) 4 (1.4g, 1.2mmol) and K 2 CO 3 (12.3 g, 89....

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Abstract

The present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device containing the same. The organic electroluminescent compounds according to the present invention can be used as a phosphorescent host material, a hole transport material, or a mixed host material; have a good hole transport ability; prevent crystallization in the production of the device; are suitable for forming a layer; and improve the current density of the device thereby reducing the driving voltage of the device.

Description

technical field [0001] The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device comprising the compound. Background technique [0002] An electroluminescence (EL) device is a self-luminous device, which has the advantage of providing a wider viewing angle, higher contrast ratio and faster response time. Eastman Kodak first developed an organic EL device [Appl. Phys. Lett. 51, 913, 1987] by using aromatic diamine small molecules and aluminum complexes as materials for forming a light-emitting layer. [0003] The most important factor determining luminous efficiency in an organic EL device is a luminescent material. Hitherto, fluorescent materials have been widely used as light emitting materials. However, from the perspective of the mechanism of electroluminescence, compared with fluorescent materials, developing phosphorescent materials is one of the best methods to theoretically increase the luminous efficiency ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D403/04C07D403/10C07D405/10C07D405/14C07D409/04C07D409/10C07D409/14C07D411/04C07D413/04C07D413/14C07D417/04C07F7/10H01L27/32H01L51/54H05B33/14
CPCH01L51/5012H01L51/0072H01L51/0071C07F7/0812C07D405/10C07D409/14C07D495/04C07D409/04C07D405/14C07D209/96C07F7/10C07D209/94C07D491/048C07D487/04C07D409/10C09B57/00C09K11/06H10K85/657H10K85/6572H10K50/11
Inventor 李泰珍梁正恩安熙春李孝姃金荣佶丘宗锡赵英俊权赫柱李暻周金奉玉
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC
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