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Compound for organic electroluminescent device and organic electroluminescent device including the same

A technology of electroluminescent devices and compounds, applied in the fields of organic semiconductor devices, organic chemistry, electric solid devices, etc., can solve the problems of voltage increase, damage to equipment, deterioration of luminous efficiency of devices, etc.

Inactive Publication Date: 2016-01-27
SK CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When the thermal stability of the material is reduced, the material may crystallize at elevated or drive temperatures, undesirably shortening the lifetime of the device
[0005] Hole-transport materials known to date for organic EL devices are problematic because thin films formed by using vacuum deposition are thermally and electrically unstable, so they rapidly crystallize due to heat generated when the device is driven, and thin-film materials will also change, thereby undesirably deteriorating the luminous efficiency of the device
Also, non-luminous parts called dark spots may gradually appear, and the voltage may increase in constant current driving, undesirably damaging the device
[0006] Meanwhile, organic EL devices using phosphorescent light-emitting materials do not confine triplet excitons generated in the light-emitting material of the light-emitting layer due to low triplet energy, thereby undesirably reducing the luminous efficiency of the device

Method used

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  • Compound for organic electroluminescent device and organic electroluminescent device including the same
  • Compound for organic electroluminescent device and organic electroluminescent device including the same
  • Compound for organic electroluminescent device and organic electroluminescent device including the same

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0102] Preparation Example 1: Synthesis of Intermediate 1 (3,5-dibromobiphenyl)

[0103]

[0104] Under a nitrogen atmosphere, place 6 g of 1,3-dibromo-5-iodobenzene, 2.2 g of phenylboronic acid, 1.5 g of tetrakis (triphenylphosphine) palladium (0) in a 250 mL three-neck round bottom flask, 4.6g of potassium carbonate, 60ml of toluene and 20ml of methanol, and stirred at 65°C for 4hrs. The reaction solution was cooled, followed by extraction with dichloromethane and water, and the extract solution was concentrated. The solution subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane was concentrated to obtain 6.08 g of 3,5-dibromobiphenyl (yield: 71%).

[0105] 1 HNMR (CDCl 3 ,600MHz)δ7.64(s,2H),7.62(s,1H),7.52-7.50(d,2H),7.46-7.43(dd,2H),7.40-7.38(dd,1H)

preparation Embodiment 2

[0106] Preparation Example 2: Synthesis of Intermediate 2 (3-(2,6-dibromophenyl)-9-phenyl-9H-carbazole)

[0107]

[0108] Under a nitrogen atmosphere, place 6 g of 1,3-dibromo-2-iodobenzene, 2.2 g of N-phenylcarbazole-3-boronic acid, 1.5 g of tetrakis(triphenyl Phosphine)palladium(0), 4.6g of potassium carbonate, 60ml of toluene and 20ml of methanol, and stirred at 65°C for 4hrs. The reaction solution was cooled, followed by extraction with dichloromethane and water, and the extract solution was concentrated. The solution subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane was concentrated to obtain 3.6 g of 3-(2,6-dibromophenyl)-9-phenyl-9H-carbazole (yield: 56%).

[0109] 1 HNMR (CDCl 3 ,600MHz)δ8.13-8.12(d,1H),7.98(s,1H),7.68-7.66(d,2H),7.63-7.60(m,4H),7.49-7.47(m,2H),7.42- 7.40(m,2H),7.33-7.23(m,2H),7.10-7.071(dd,1H)

preparation Embodiment 3

[0110] Preparation Example 3: Synthesis of Intermediate 3 (3,5-bis(diphenylamine)-1-bromobenzene)

[0111]

[0112] Under a nitrogen atmosphere, place 9 g of 1,3,5-tribromobenzene, 8 g of diphenylamine, 9 g of sodium tert-butoxide, and 0.5 g of tris(dibenzylideneacetone) dipalladium in a three-neck round bottom flask (0), 0.3 g of triphenylphosphine and 200 ml of toluene were dissolved and then stirred while maintaining the temperature at 80°C. After the reaction was completed, the reaction solution was extracted with dichloromethane and water, and concentrated. The solution subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane was concentrated to obtain 5 g of 3,5-bis(diphenylamine)-1-bromobenzene (yield: 35%).

[0113] 1 HNMR (CDCl 3 ,600MHz)δ7.24-7.21(t,8H),7.08-7.06(d,8H),7.02-7.00(t,4H),6.75-6.74(d,2H),6.71-6.70(d,1H)

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Abstract

This invention relates to a compound for an organic electroluminescent device and to an organic electroluminescent device including the same. According to the present invention, the organic electroluminescent device including the compound may have improved thermal stability and light emission efficiency. When the compound is used as a hole transport layer material, a triplet energy of a phosphorescent light emitting material increase, thus improving efficiency of the organic electroluminescent device.

Description

technical field [0001] The present invention relates to a compound for an organic electroluminescent device and an organic electroluminescent device containing the compound, more particularly, the present invention relates to a compound for an organic electroluminescent device having improved luminous efficiency and a compound containing the same Compound organic electroluminescent devices. Background technique [0002] Compared with other flat panel displays (eg, liquid crystal displays (LCDs), plasma display panels (PDPs), field emission displays (FEDs), etc.), organic electroluminescent (EL) devices have simpler structures, various processing advantages, and relatively High brightness, excellent viewing angle characteristics, fast response speed, and low driving voltage, so it is also fully developed to be used as a light source for flat panel displays (such as wall-mounted TVs, etc.), or as a display, lighting backlight unit for monitors, advertising boards, etc. [00...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07C211/54H01L51/50
CPCC07C211/54C09K11/06C07D209/86C09K2211/1007C07C2603/18H10K85/631H10K2101/30H10K85/621H10K85/624H10K85/649H10K50/11H10K50/12H10K85/636H10K50/156H10K85/6572H10K2101/40
Inventor 姜周植朴正镐全锡云愼镛埈张有美杨南喆朴宰均李松
Owner SK CHEM CO LTD
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