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Indenocarbazole compound and organic electroluminescent element

An electroluminescent element, indenocarbazole technology, applied in the field of indenocarbazole compounds and organic electroluminescent elements, to achieve the effects of low manufacturing cost, high electron blocking property, and excellent heat resistance

Active Publication Date: 2019-06-04
HODOGOYA CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] However, according to Patent Document 4, only a slight improvement in power efficiency is found in an organic EL device in which this compound is used in an electron blocking layer.
In addition, there is no description of an organic EL element using this compound and using a heat-activated delayed fluorescent material as a dopant material in the light-emitting layer.

Method used

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  • Indenocarbazole compound and organic electroluminescent element
  • Indenocarbazole compound and organic electroluminescent element
  • Indenocarbazole compound and organic electroluminescent element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0215]

[0216] 7-(12,12-Dimethyl-indeno[2,1-b]carbazol-10-yl)-10-phenyl-12,12-dimethyl-indeno[2,1-b] Synthesis of carbazole;

[0217] In a reaction vessel replaced with nitrogen, add

[0218]

[0219] , heated, and stirred at 120° C. for 5 hours to obtain a reaction solution. After the reaction liquid was naturally cooled to room temperature, water was added, and an extraction operation using toluene was performed. The extracted organic layer was concentrated to obtain a crude product. The crude product was purified by column chromatography (carrier: silica gel, eluent: toluene / hexane). As a result, a white solid of Compound 1 was obtained (83% yield).

[0220] For the obtained white solid, NMR was used to identify the structure. put it 1 The H-NMR diagram is shown in figure 1 middle. use 1 H-NMR (CDCl 3 ) detected the following 36 hydrogen signals.

[0221] δ(ppm)=8.49(1H)

[0222] 8.44(1H)

[0223] 8.41(1H)

[0224] 8.24(1H)

[0225] 7.88(1H)

[0226] 7...

Embodiment 2

[0234]

[0235] Synthesis of 7-(carbazol-9-yl)-10-phenyl-12,12-dimethyl-indeno[2,1-b]carbazole;

[0236] In a reaction vessel replaced with nitrogen, add

[0237]

[0238] , heated, and stirred at 120° C. for 5 hours to obtain a reaction solution. After the reaction liquid was naturally cooled to room temperature, water was added, and an extraction operation using toluene was performed. The extracted organic layer was concentrated to obtain a crude product. The crude product was purified by column chromatography (carrier: silica gel, eluent: toluene / hexane). As a result, a white solid of Compound 2 was obtained (60% yield).

[0239] For the obtained white solid, NMR was used to identify the structure. put it 1 The H-NMR diagram is shown in figure 2 middle. use 1 H-NMR (CDCl 3 ) detected the following 28 hydrogen signals.

[0240] δ(ppm)=8.41(1H)

[0241] 8.34(1H)

[0242] 8.19(2H)

[0243] 7.80(1H)

[0244] 7.75-7.68(4H)

[0245] 7.62-7.50(3H)

[0246] 7....

Embodiment 3

[0251]

[0252] Synthesis of 7-(carbazol-9-yl)-10-(biphenyl-4-yl)-12,12-dimethyl-indeno[2,1-b]carbazole;

[0253] In a reaction vessel replaced with nitrogen, add

[0254]

[0255] , heated, and stirred at 110° C. for 5 hours to obtain a reaction solution. After the reaction liquid was naturally cooled to room temperature, water was added, and an extraction operation using toluene was performed. The extracted organic layer was concentrated to obtain a crude product. The crude product was purified by column chromatography (carrier: silica gel, eluent: toluene / hexane). As a result, compound 3 was obtained as a white solid (yield 56%).

[0256] For the obtained white solid, NMR was used to identify the structure. put it 1 The H-NMR diagram is shown in image 3 middle. use 1 H-NMR (CDCl 3 ) detected the following 32 hydrogen signals.

[0257] δ(ppm)=8.42(1H)

[0258] 8.35(1H)

[0259] 8.20(2H)

[0260] 7.96-7.88(2H)

[0261] 7.84-7.73(5H)

[0262] 7.63(1H)

[02...

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Abstract

The present invention provides: an indenocarbazole compound which has hole transport properties and is used as a constituent material for organic electroluminescent elements, and which is characterized by being represented by general formula (1); and an organic electroluminescent element which comprises a pair of electrodes and at least one organic layer sandwiched between the pair of electrodes,and which is characterized in that the above-described indenocarbazole compound is used as a constituent material for the at least one organic layer. An indenocarbazole compound according to the present invention has (1) excellent hole transport properties, (2) excellent electron blocking properties, and (3) good stability in a thin film state, while exhibiting excellent heat resistance. In addition, an organic electroluminescent element according to the present invention has high luminous efficiency and high luminance.

Description

technical field [0001] The present invention relates to suitable compounds and organic EL elements in organic electroluminescence elements (hereinafter sometimes referred to as organic EL elements) suitable for various display devices, and specifically relates to specific indenocarbazole compounds and the use of the same Compound organic EL elements. Background technique [0002] An organic EL element is a self-luminous element, which is brighter than a liquid crystal element, has excellent visibility, and can perform a clear display, so active research has been conducted. [0003] In recent years, as an attempt to improve the luminous efficiency of a device, a device that generates phosphorescence using a phosphorescent emitter, that is, utilizes light emission from a triplet excited state, has been developed. According to the theory of the excited state, when phosphorescence is used, it is expected that a remarkable improvement in luminous efficiency can be achieved, whic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/50C07D209/86H10K99/00
CPCC07D209/86H10K85/6574H10K85/6572H10K2101/20H10K50/15H10K50/181H10K71/12H10K50/85H10K71/135H10K50/17C07D209/94C07D405/14C09K11/06C09K2211/1025H10K50/11H10K50/18H10K2101/10
Inventor 高桥岳洋北原秀良泉田淳一
Owner HODOGOYA CHEMICAL CO LTD