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Organic electroluminescent compound and organic electroluminescent device comprising the same

An electroluminescence and compound technology, applied in the field of organic electroluminescence compounds, can solve the problems of no advantage in power efficiency, high driving voltage, low glass transition temperature, etc., and achieve excellent life characteristics, low driving voltage, and high luminous efficiency. Effect

Pending Publication Date: 2020-05-01
ROHM & HAAS ELECTRONICS MATERIALS LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Although these materials provide good light-emitting characteristics, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, they may degrade during the high-temperature deposition process in vacuum and the lifetime of the device is reduced
Although organic electroluminescent devices containing phosphorescent host materials offer higher current efficiencies (cd / A) than organic electroluminescent devices containing fluorescent materials, considerably higher driving voltages are required
Therefore, there is no advantage in terms of power efficiency (lm / W)
(3) Further, when these materials are used in organic electroluminescent devices, the operating life of organic electroluminescent devices is short and there is still a need to improve luminous efficiency
Further, not sufficiently satisfactory in terms of lifetime characteristics of the device

Method used

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  • Organic electroluminescent compound and organic electroluminescent device comprising the same
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  • Organic electroluminescent compound and organic electroluminescent device comprising the same

Examples

Experimental program
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Effect test

example 1

[0152] Example 1: Preparation of Compound C-2

[0153]

[0154] Synthesis of Compound 1-1

[0155] In a flask, 17 g of 4-chlorobenzene-1,2-diamine (142 mmol) and 30 g of benzyl (119 mmol) were dissolved in 600 mL of ethanol, and the mixture was stirred at 110° C. for 4 hours. After the reaction was completed, the obtained solid was filtered, dried and separated by column chromatography to obtain 20 g of compound 1-1 (yield: 53%).

[0156] Synthesis of Compound C-2

[0157] In a flask, 6.95 g of compound 1-1 (21.0 mmol), 7 g of 7-phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (19.3 mmol) were mixed ), 833 mg of Pd 2 (dba) 3 (0.915 mmol), 751 mg of 2-dichlorohexylphosphino-2',6'-dimethoxybiphenyl (s-Phos) (1.83 mmol), and 5.27 g of NaOtBu (54.9 mmol) were dissolved in 100 mL of o-xylene, and the mixture was refluxed at 180°C for 2 hours. After the reaction was completed, the reactant was filtered with celite, dried and separated by column chromatography to obtain...

example 2

[0160] Example 2: Preparation of Compound C-62

[0161]

[0162] In a flask, 6.9 g of compound 1-1 (25.3 mmol), 7 g of 14-phenyl-12,14-dihydrobenzo[a]indolo[3,2-h]carbazole (21.1 mmol) were mixed ), 960 mg of Pd 2 (dba) 3 (1.055 mmol), 866 mg of s-Phos (2.11 mmol), and 6 g of NaOtBu (63.3 mmol) were dissolved in 100 mL of o-xylene, and the mixture was refluxed at 180° C. for 2 hours. After the reaction was completed, the reactant was filtered with celite, dried and separated by column chromatography to obtain 11 g of compound C-62 (yield: 85%).

[0163] 1 H NMR (600MHz, DMSO, δ) 8.895 (s, 1H), 8.375-8.361 (m, 2H), 8.303-8.285 (m, 2H), 7.971-7.949 (m, 2H) 7.771-7.757 (d, J= 84Hz, 1H), 7.572-7.504 (m, 10H), 7.390-7.305 (m, 10H), 7.135-7.134 (d, J=6Hz, 2H)

[0164] compound MW melting point C-62 662.80 245℃

example 3

[0165] Example 3: Preparation of Compound C-32

[0166]

[0167] In a flask, 8.9 g of compound 1-1 (25.3 mmol), 7 g of 5-phenyl-5,7-indolino[2,3-b]carbazole (21.1 mmol), 960 mg of Pd 2 (dba) 3 (1.055 mmol), 866 mg of s-Phos (2.11 mmol), and 6 g of NaOtBu (63.3 mmol) were dissolved in 100 mL of o-xylene, and the mixture was refluxed at 180° C. for 2 hours. After the reaction was completed, the reactant was filtered with celite, dried and separated by column chromatography to obtain 11 g of compound C-32 (yield: 85%).

[0168] 1 H NMR (600MHz, DMSO, δ) 8.865 (s, 1H), 8.403 (s, 1H), 8.345-8.330 (d, J=90Hz, 1H), 8.288-8.263 (m, 2H) 8.010-7.992 (m, 1H), 7.577-7.522 (m, 9H), 7.490 (s, 1H), 7.423-7.352 (m, 13H)

[0169] compound MW melting point C-32 612.74 224℃

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Abstract

The present disclosure relates to an organic electroluminescent compound, and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound of the present disclosure, an organic electroluminescent device having improved driving voltage, luminous efficiency, lifespan characteristic, and / or power efficiency can be provided.

Description

technical field [0001] The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device including the same. Background technique [0002] An electroluminescent device (EL device) is a self-luminous device that has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time. The first organic EL device was developed by Eastman Kodak in 1987 by using small aromatic diamine molecules and aluminum complexes as materials for forming the light-emitting layer [see Appl.Phys.Lett . [Applied Physics Letters] 51, 913, 1987]. [0003] The most important factor determining the luminous efficiency in an organic electroluminescent device is the luminescent material. So far, fluorescent materials have been widely used as light-emitting materials. However, in view of the electroluminescence mechanism, since the phosphorescent light-emitting material theoretically enhances the luminous efficien...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06H01L51/50H10K99/00
CPCH10K85/631H10K85/654H10K85/6572H10K85/342H10K50/11H10K2101/10C09K11/06C09K2211/1044H10K50/00C09K2211/1059C09K2211/1074H10K85/6574H10K85/6576
Inventor S-Y·钟李琇炫赵诚昱
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC