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Indene benzophenanthrene derivative and organic light-emitting device using same

A technology of indenatriphenylene and derivatives is applied in the fields of indenatriphenylene derivatives and organic electroluminescence devices, and can solve problems such as incapability of industrial application and the like

Active Publication Date: 2014-01-15
颜丰文
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These compounds still have the defect of not being able to be applied industrially

Method used

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  • Indene benzophenanthrene derivative and organic light-emitting device using same
  • Indene benzophenanthrene derivative and organic light-emitting device using same
  • Indene benzophenanthrene derivative and organic light-emitting device using same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Synthesis of compound A12

[0046] Synthesis of 2-(diphenyl-2-yl)-7-bromo-9,9-dimethyl-9H-fluorene

[0047]

[0048] 35.2g (100mmol) 2,7-dibromo-9,9-dimethyl-9H-fluorene, 21.8g (110mmol) diphenyl-2-ylboronic acid, 2.31g (2mmol) tetrakis (triphenylphosphine ) Palladium, 75ml 2M Na 2 CO 3 , A mixture of 150ml EtOH and 300ml toluene was degassed and placed under nitrogen, then heated at 100°C for 12h. After the reaction was complete, the mixture was cooled to room temperature. The organic layer was extracted with ethyl acetate and water, dried over anhydrous magnesium sulfate, the solvent was removed, and the residue was purified by silica gel column chromatography (hexane-dichloromethane) to obtain a white solid product (26.8g, 63.0mmol, 63%). 1 H NMR (CDCl 3 ,400MHz): chemical shift (ppm)7.61(d,J=7.8Hz,1H),7.55~7.53(m,2H),7.49~7.42(m,5H),7.29(d,J=8.0Hz,1H) ,7.20~7.14(m,5H),6.98(s,1H),1.21(s,6H)

[0049] Synthesis of 12-bromo-10,10-dimethyl-10H-indeno[1,2-b]triphe...

Embodiment 2

[0065] Synthesis of Compound A13

[0066] Synthesis of 1-bromo-6-(naphthalen-1-yl)pyrene

[0067]

[0068] 27.2g (75.6mmol) 1,6-dibromopyrene, 13g (75.6mmol) naphthalene-1-yl boronic acid, 0.87g (0.756mmol) tetrakis (triphenylphosphine) palladium, 57ml 2M Na 2 CO 3 A mixture of , 120 ml EtOH and 300 ml toluene was degassed and placed under nitrogen, then heated at 90° C. for 24 h. After the reaction was complete, the mixture was cooled to room temperature. Then 500 ml of MeOH were added with stirring, and the precipitated product was filtered off with suction. Recrystallization from 1,4-dioxane gave 14 g of a brown product (yield 45.5%).

[0069] Synthesis of 10,10-Dimethyl-12-(6-(naphthalen-1-yl)pyren-1-yl)-10H-indeno[1,2-b]triphenylene

[0070]

[0071] 7g (17.2mmol) of 1-bromo-6-(naphthalene-1-yl)pyrene, 8.1g (17.2mmol) of 2-(10,10-dimethyl-10H-indeno[1,2-b]benzene Phenanthrene-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.2g (0.172mmol) tetrakis(triphenylph...

Embodiment 3

[0073] Synthesis of Compound A15

[0074] Synthesis of 9-bromo-10-(naphthalene-2-yl)anthracene

[0075]

[0076] 15g (44.6mmol) 9,10-dibromoanthracene, 7.7g (44.6mmol) naphthalene-2-ylboronic acid, 0.52g (0.446mmol) tetrakis (triphenylphosphine) palladium, 33ml2M Na 2 CO 3 A mixture of , 60 ml EtOH and 150 ml toluene was degassed and placed under nitrogen, then heated at 90° C. for 24 h. After the reaction was complete, the mixture was cooled to room temperature. The organic layer was extracted with ethyl acetate and water, dried over anhydrous magnesium sulfate, the solvent was removed, and the residue was purified by silica gel column chromatography (hexane-dichloromethane) to obtain 10.4 g (61%) of a yellow solid product.

[0077] Synthesis of 10,10-Dimethyl-12-(10-(naphthalene-2-yl)anthracen-9-yl)-10H-indeno[1,2-b]triphenylene

[0078]

[0079] 6.6g (17.2mmol) 9-bromo-10-(naphthalene-2-yl) anthracene, 8.1g (17.2mmol) 2-(10,10-dimethyl-10H-indeno[1,2-b] Triphenylen...

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Abstract

The invention discloses a novel indene benzophenanthrene derivative and an organic light-emitting device using same. The organic light-emitting device using the novel indene benzophenanthrene derivative as a host material can lower the driving voltage, prolong the half-life period, and improve the efficiency. The novel indene benzophenanthrene derivative is shown in the formula (A) in the specification: in formula (A), A1 and A2 are substituted or unsubstituted combined hydrocarbon ring units with 1-5 rings; preferably, A1 and A2 are phenyl, naphthyl, anthryl, pyrenyl, chrysene and perylene; R1-R4 are the same or different and are independently selected from hydrogen atom, halogen, alkyl group with 1-20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted aralkyl with 6-30 carbon atoms, and substituted or unsubstituted ceteroary with 6-30 carbon atoms; and X can be carbon atom or nitrogen atom.

Description

technical field [0001] The present invention generally relates to indenotriphenylene derivatives and organic electroluminescent devices using the derivatives. More specifically, the present invention relates to indenotriphenylene derivatives having the general formula (A), and an organic electroluminescent device containing indenotriphenylene derivatives as light-emitting layer materials can reduce driving voltage, prolong half-life, and improve efficiency and increase the stability of organic electroluminescent devices. Background technique [0002] Organic electroluminescent devices (OLEDs) have attracted much attention because of their potential applications in full-color flat panel displays. In particular, small-sized AMOLED panels have been mounted on smartphones in these years. OLEDs usually consist of functionally divided organic multilayers, such as hole injection layer (HIL), hole transport layer (HTL), light emitting layer (EML), electron transport layer (ETL), a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C13/62C07D221/18C07D471/04C07C1/32H01L51/54
Inventor 颜丰文
Owner 颜丰文
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