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Novel organic electroluminescent compounds and organic electroluminescent device comprising the same

An electroluminescent device and compound technology, which can be used in organic chemistry, compounds of Group 4/14 elements of the periodic table, luminescent materials, etc. Satisfaction and other issues, to achieve the effect of reducing power consumption and high luminous efficiency

Active Publication Date: 2016-07-06
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) Due to their low glass transition temperature and poor thermal stability, they may decompose during high temperature deposition processes in vacuum
Therefore, organic EL devices using conventional phosphorescent host materials have no advantage in terms of power efficiency (lm / W)
(3) In addition, the operating life and luminous efficacy of organic EL devices are unsatisfactory
However, organic EL devices comprising the compounds described in the above publications still do not meet the requirements of power efficiency, luminous efficiency, lifetime, etc.

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
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Effect test

example 1

[0105] Example 1: Preparation of compound H-34

[0106]

[0107] Preparation of Compound 1-2

[0108] 2-Bromobiphenyl (50.0 g, 214.0 mmol) and tetrahydrofuran (THF) (1.0 L) were cooled to -78 °C in a 3 L round bottom flask (RBF) and 2.5 M n-butyllithium (103.0 mL, 257.0 mmol). After 2 hours, (4-bromophenyl)(phenyl)methanone (56.0 g, 214.0 mmol) was added to the flask. After 17 hours, with dichloromethane (MC) and H 2 O extracted the mixture, and subjected the MC layer to MgSO 4 dry. The MC layer was concentrated to obtain compound 1-1.

[0109] Compound 1-1, hydrochloric acid (100.0 mL) and acetic acid (1.0 L) were stirred under reflux in a 3LRBF. After 14 hours, the resulting solid was filtered, and the filtered solid was dissolved in chloroform (CHCl 3 ), and applied to column chromatography to obtain compound 1-2 (35.0 g, 42%).

[0110] Preparation of Compounds 1-3

[0111] Compound 1-2 (35.0 g, 89.0 mmol), bis(pinacolate) diborane (27.0 g, 106.0 mmol), bi...

example 2

[0123] Example 2: Preparation of Compound H-57

[0124]

[0125] Preparation of compound 2-1

[0126] Compound 1-3 (35.0 g, 78.0 mmol), 2,5-dibromonitrobenzene (26.2 g, 93.0 mmol), Pd(PPh 3 ) 4 (3.6g, 3.1mmol), Na 2 CO 3 (20.6g, 195.0mmol), toluene (400.0mL), EtOH (50.0mL) and H 2 O (100.0 mL) overnight. with ethyl acetate (EA) and H 2 O treated the reaction mixture with MgSO 4 Water was removed, and the residue was distilled under reduced pressure. The crude product was applied to column chromatography with MC:hexane (Hx) to obtain compound 2-1 (30.0 g, 75%) as a solid.

[0127] Preparation of compound 2-2

[0128] Compound 2-1 (30.0 g, 57.8 mmol), P(OEt) was stirred in 1 LRBF at 150 °C 3 (200.0 mL) and 1,2-DCB (200.0 mL) for 2 hours. The reaction mixture was distilled to obtain a solid. The crude product was applied to column chromatography with MC:Hx to obtain compound 2-2 (19.0 g, 68%) as a white solid.

[0129] Preparation of Compound 2-3

[0130]...

example 3

[0134] Example 3: Preparation of Compound H-90

[0135]

[0136] Preparation of compound 3-1

[0137] 9-Fluorenone (20.0 g, 111.0 mmol) was dissolved in THF (554.0 mL) in a flask and phenylmagnesium bromide (36.9 mL) was slowly added thereto at 0°C. The mixture was stirred at room temperature for 24 hours. After the reaction was complete, the organic layer was extracted with EA and 4 Remove remaining moisture and dry. The layers were separated by column chromatography to obtain compound 3-1 (20.0 g, 70%).

[0138] Preparation of compound 3-2

[0139] 2-Bromo-9H-carbazole (20.0 g, 81.2 mmol), phenylboronic acid (11.9 g, 97.5 mmol), Pd(PPh 3 ) 4 (4.7g, 4.06mmol), 2MK 2 CO 3 (121.0 mL), toluene (250.0 mL), and EtOH (121.0 mL) for 5 hours. After the reaction was complete, the organic layer was extracted with EA and 4 Remove remaining moisture and dry. The layers were separated by column chromatography to obtain compound 3-2 (17.0 g, 86%).

[0140] Preparatio...

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Abstract

The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device comprising the same. The organic electroluminescent compound according to the present invention can be used in a light-emitting layer and has excellent luminescent efficiency; and an organic electroluminescent device comprising the organic electroluminescent compounds of the present invention has long life span, and improved current efficiency and power efficiency.

Description

technical field [0001] The present invention relates to novel organic electroluminescent compounds and organic electroluminescent devices containing said compounds. Background technique [0002] Electroluminescent (EL) devices are self-luminous devices that have the advantage of providing wider viewing angles, greater contrast ratios, and faster response times. The organic EL device was originally developed by Eastman Kodak by using small aromatic diamine molecules and aluminum complexes as materials for forming the light emitting layer (see Appl. Phys. Lett. 51, 913, 1987). [0003] An organic EL device generally includes an anode, a cathode, and an organic layer formed between the two electrodes and emits light when an excited state is formed by recombination thereof by holes injected from the anode and electrons injected from the cathode and then the excited state returns to a ground state. The organic layer of an organic EL device can be composed of a hole injection la...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07D403/04C07D403/10C07D403/14C07D407/14C07D409/14C07D417/14C07F7/10C07D487/04C07D491/048C07D495/04C07D207/33H01L27/32H01L51/54
CPCC07D401/04C07D403/04C07D403/10C07D403/14C07D409/14C07F7/0812C07D401/14C07D405/14H10K85/615H10K85/654H10K85/6572H10K50/11H10K2101/10C09K11/06H10K50/00
Inventor K-J·李C-S·金S-W·李S-H·李J-E·杨Y-K·金H-J·李Y-J·曹K-J·朴
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC
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