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Novel organic electroluminescent compounds and organic electroluminescent devices including the same

An electroluminescence and compound technology, applied in the field of organic electroluminescence devices, which can solve the problems of high amorphousness and inability to provide durable luminous efficiency of organic EL devices.

Inactive Publication Date: 2013-05-22
ROHM & HAAS ELECTRONICS MATERIALS LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The glass transition temperature of existing MTDATA is 76°C, but this does not indicate high non-crystallinity
Such materials cannot provide characteristics required in terms of durability of organic EL devices and luminous efficiency due to hole injection and transport characteristics

Method used

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  • Novel organic electroluminescent compounds and organic electroluminescent devices including the same
  • Novel organic electroluminescent compounds and organic electroluminescent devices including the same
  • Novel organic electroluminescent compounds and organic electroluminescent devices including the same

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0057] [Preparation Example 1] Preparation of Compound 1

[0058]

[0059] Preparation of compound 1-1

[0060] Add 3-bromo-9-phenyl-9H-carbazole 30g (93.1mmol), aniline 26mL (279.3mmol), Pd(OAc) 2 0.63g(2.79mmol), P(t-Bu) 3 4.3mL (9.31mmol), Cs 2 CO 3 76g (232.8mmol) and toluene 700mL, then heated and stirred at 120°C for 12 hours. After the reaction was completed, the resulting substance was washed with distilled water and extracted with ethyl acetate. with MgSO 4 The organic layer was dried and the solvent was removed with a rotary evaporator, followed by purification using column chromatography to obtain Compound 1-1 (20 g, 59.8 mmol).

[0061] Preparation of compound 1-2

[0062] Add 10.5g (46mmol) of 4-dibenzothiophene boronic acid, 32.6g (138mmol) of 1,4-dibromobenzene, Pd(PPh 3 ) 4 0.53g (0.46mmol), 1M Na 2 CO 3 69mL (69mmol) and toluene 600mL, and then stirred at reflux at 70°C for 2 hours. After the reaction was completed, the resulting substance w...

preparation example 2

[0066] [Preparation Example 2] Preparation of Compound 9

[0067]

[0068] Preparation of compound 2-1

[0069] In the reactor, add 2-naphthol 20.0g (138.8mmol), NaHSO 3 28.8g (277.4mmol), 400mL of distilled water, 31.2mL (166.4mmol) of 4-bromophenylhydrazine, and then heated to 120°C. After 12 hours, distilled water was added thereto, and the resulting solid was filtered under reduced pressure. The obtained solid was put into an aqueous hydrochloric acid solution, followed by heating at 100°C. After 1 hour, the resulting material was extracted with dichloromethane, washed with distilled water and aqueous NaOH. Column separation was then performed to obtain compound 2-1 (9.2 g, 31.0 mmol).

[0070] Preparation of Compound 2-2

[0071] Add compound 2-19.2g (31.0mmol), Cu2.0g (31.0mmol), 18-crown-60.4g (1.6mmol), K 2 CO 3 12.8g (93.2mmol) and 100mL of 1,2-dichlorobenzene were then stirred at reflux at 180°C for 12 hours. The resulting material was cooled at room t...

preparation example 3

[0079] [Preparation Example 3] Preparation of Compound 27

[0080]

[0081] Preparation of compound 3-1

[0082] Add 5.4g (44mmol) of phenylboronic acid, 18.9g (66mmol) of 1,4-dibromonaphthalene, Pd(PPh 3 ) 4 2.0g (1.76mmol), Na 2 CO 3 14.0 g (132 mmol), 200 mL of toluene, and 100 mL of ethanol were then stirred at reflux at 120° C. for 12 hours. After the reaction was completed, the resulting substance was washed with distilled water and extracted with ethyl acetate. with MgSO 4 The organic layer was dried and the solvent was removed with a rotary evaporator, followed by purification using column chromatography to obtain compound 3-1 (9.1 g, 32.14 mmol).

[0083] Preparation of Compound 3-2

[0084] Add compound 3-126.4g (93.1mmol), compound 2-372.1g (279.3mmol), Pd(OAc) in the reactor 2 0.63g(2.79mmol), P(t-Bu) 3 4.3mL (9.31mmol), Cs 2 CO 3 76g (232.8mmol) and toluene 1000mL were then heated and stirred at 120°C for 12 hours. After the reaction was complet...

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Abstract

Provided are a novel organic electroluminescent compound and an organic electroluminescent device including the same. The organic electroluminescent device, which uses the organic electroluminescent compound according to the present invention as a hole transfer material or a hole injection material, has better luminous efficiency and excellent lifespan property of materials than the existing materials. Therefore, an OLED device, which has excellent driving lifespan property and improved power consumption due to an increase of power efficiency, can be manufactured.

Description

technical field [0001] The present invention relates to a new organic electroluminescent compound and an organic electroluminescent device comprising the same, more particularly to a new organic electroluminescent compound used as a hole transport material or a hole injection material and an organic electroluminescent device using the compound Light emitting devices. technical background [0002] Liquid crystal displays (LCDs), which are most widely used today, are non-emitting display devices that consume little power and are light in weight. However, its device driving system is complicated, and the response time and its contrast cannot reach the desired level. Therefore, research on organic electroluminescent devices as next-generation flat panel displays has drawn attention and been actively developed. [0003] Among display devices, electroluminescent devices (EL devices) are self-luminous display devices, which have the advantages of wide viewing angle, excellent con...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D209/82H01L27/32H01L51/50H05B33/14
CPCH01L51/0072C09K2211/1092C07D209/86C09K2211/1029H01L51/0085C07D409/12H01L51/5056C07D409/14H01L51/5088H05B33/22H01L51/0074C09K11/06H01L51/0061C09K2211/1088H01L51/0081C07D209/88H10K85/636H10K85/6576H10K85/6572H10K85/324H10K85/342H10K50/15H10K50/17C07D333/72
Inventor 李秀镛李孝姃罗弘烨权赫柱金奉玉金圣珉
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC
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