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Novel organic electroluminescent compounds and organic electroluminescent device using the same

An electroluminescence device and luminescence technology, which are applied in electroluminescence light sources, organic chemistry, compounds of group 4/14 elements of the periodic table, etc., can solve the problem of no obvious advantage in power efficiency, OLED equipment does not have a working life, High driving voltage and other issues, to achieve good luminous efficiency, good working life, and excellent life properties

Active Publication Date: 2012-08-01
ROHM & HAAS ELECTRONICS MATERIALS LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when existing materials such as BAlq, CBP, etc. are used as hosts of phosphorescent materials, there is no obvious advantage in power efficiency (lm / W) compared to OLEDs using fluorescent materials because of higher driving voltages.
[0007] In addition, OLED devices do not have a satisfactory working life

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0052] [Preparation Example 1] Preparation of Compound A

[0053]

[0054] Preparation of Compound A-1

[0055] Mix 1-bromonitrobenzene (16g, 74.25mmol), 9,9-dimethyl-9H-fluoren-2-ylboronic acid (23g, 96.60mmol), Pd(PPh 3 ) 4 (4.2g, 3.63mmol), 2M K 2 CO 3 Aqueous solution (111 mL), EtOH (100 mL) and toluene (200 mL), and heated to reflux at 120° C. for 3 hours. After the reaction was completed, the mixture was washed with distilled water. Extraction with EA and MgSO 4 After drying the organic layer, the solvent was removed using a rotary evaporator. The residue was purified by column chromatography to obtain compound (A-1) (22 g, 95%).

[0056] Preparation of Compound A-2

[0057] Compound A-1 (24 g, 76.10 mmol), triethyl phosphite (200 mL) and 1,2-dichlorobenzene (200 mL) were mixed, heated to 180° C., and stirred for 12 hours. When the reaction was completed, unreacted triethyl phosphite and 1,2-dichlorobenzene were removed using a distillation apparatus, and the...

preparation example 2

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

[0067]

[0068] Preparation of Compound B-2

[0069] Compound B-1 (50.0 g, 179 mmol) was dissolved in DMF (200 mL), and copper powder (27.0 g, 424 mmol) was added thereto. The mixture was stirred at 125°C for 3 hours. The reaction mixture was cooled at room temperature, filtered and the precipitate was removed and dried. Washing with MeOH (500 mL) gave compound B-2 (27.1 g, 88%).

[0070] Preparation of Compound B-3

[0071]Compound B-2 (15 g, 37.3 mmol) was dissolved in ethanol (200 mL), and 32% (w / w) HCl aqueous solution (120 mL) was added thereto. Tin powder (17.6 g, 147 mmol) was added in portions within 10 minutes at room temperature, and stirred at 100° C. for 2 hours. After cooling at room temperature, the reaction mixture was added to ice water and made basic using 20% ​​(w / w) aqueous NaOH (150 mL). Extracted with diethyl ether, washed with brine (bryn) and dried. Recrystallization from ethanol gave C...

preparation example 3

[0089] [Preparation Example 3] Preparation of Compound C

[0090]

[0091] Preparation of Compound C-1

[0092] Compound C-1 (1.7 g, 50%) was prepared in the same manner as Compound B-5 in Preparation 2, using Compound B-4 as a starting material, except that dichlorodiphenylsilane was used instead of dichlorodimethylsilane.

[0093] Preparation of Compound C

[0094] Compound C (347 mg, 55%) was prepared in the same manner as Compounds B-6, B-8, B-9, B-10 and B in Preparation 2 using Compound C-1 as a starting material.

[0095] Prepare organic electroluminescence compound TA, TB and TC according to the method for preparation example 1-3, table 1-4 has listed 1 H NMR and MS / FAB, which are substituted versions of the prepared organic electroluminescent compounds.

[0096] Table 1

[0097]

[0098]

[0099]

[0100]

[0101]

[0102] Table 2

[0103]

[0104]

[0105]

[0106]

[0107] table 3

[0108]

[0109]

[0110]

[0111] Table...

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PUM

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Abstract

Provided are a novel organic electroluminescent compound and an organic electroluminescent device using the same. When used as a host material of an organic electroluminescent material of an OLED device, the organic electroluminescent compound disclosed herein exhibits good luminous efficiency and excellent life property as compared to the existing host material. Therefore, it may be used to manufacture OLEDs having very superior operation life.

Description

technical field [0001] The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device using the compound, and more particularly, to an organic electroluminescent compound used as an electroluminescent material and an organic electroluminescent compound using the compound as a substrate. Luminous device. Background technique [0002] The most important factor in determining the luminous efficiency of an OLED is the electroluminescent material. Currently, fluorescent materials are widely used as electroluminescent materials. However, phosphorescent materials are better when considering the mechanism of electroluminescence. Theoretically, phosphorescent materials can increase the luminous efficiency by 4 times (4-fold). Phosphorescent materials based on iridium(III) complexes are well known so far. Such materials as (acac)Ir(btp) 2 、Ir(ppy) 3 and Firpic are known for red, green and blue respectively. Currently, many ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C09K11/65H01L51/50C07D209/82H01L51/00H05B33/14H10K99/00
CPCH05B33/10C09K2211/1011C07D209/82H01L51/0067H01L51/0072C07D471/04C07F7/0816C07D209/86C09K2211/1029C09K2211/1096C09B57/00C09K2211/1007C07D471/22C09K11/06C07D471/14H01L51/0094C09B5/24H01L51/5016C07D401/04C07D209/80C07D401/14C07D403/04C07D409/04C07D413/04C07D417/04C07D487/04C07D401/10C07D403/06C07D403/08C07D403/10C07D417/10C07F7/0812C09K2211/1092C09K2211/1059C09K2211/1033C09K2211/1037C09K2211/1044H10K85/615H10K85/626H10K85/656H10K85/654H10K85/655H10K85/6565H10K85/657H10K85/6576H10K85/40H10K85/6572H10K50/11H10K2101/10
Inventor 李秀镛金荣佶赵英俊权赫柱金奉玉金圣珉尹勝洙
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC
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