Phenanthro[9,10-b]tetraphenylene derivative and use thereof

A technology of tetraphenylene and derivatives, applied in the field of organic electroluminescent devices, to achieve the effects of short half-life, low efficiency, and high power consumption

Active Publication Date: 2016-07-27
NINGBO LUMILAN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, fluorescent electroluminescent devices have only 25% internal quantum efficiency

Method used

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  • Phenanthro[9,10-b]tetraphenylene derivative and use thereof
  • Phenanthro[9,10-b]tetraphenylene derivative and use thereof
  • Phenanthro[9,10-b]tetraphenylene derivative and use thereof

Examples

Experimental program
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Effect test

example 1

[0083] Synthesis of 4-(spiro[fluorene-9,10'-indeno[1,2-b]triphenylene]-13'-yl)dibenzo[b,d]thiophene

[0084]

[0085] Make 5.5g (10.1mmol) of 13'-bromospiro[fluorene-9,10'-indeno[1,2-b]triphenylene], 2.7g (12mmol) of dibenzo[b,d]thiophene- 4-ylboronic acid, 0.22g (0.2mmol) tetrakis (triphenylphosphine) palladium, 15ml 2M Na 2 CO 3 A mixture of , 20 ml EtOH and 40 ml toluene was degassed and placed under nitrogen, and then heated at 90° C. overnight. After the reaction was complete, the mixture was cooled to room temperature. The solution was extracted with 100 mL ethyl acetate and 500 mL water. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography (Hx-CH 2 Cl 2 ) to obtain the product 4.1 g (63%). MS (m / z, FAB + ):648.1

example 2

[0087] Synthesis of 4-(3-bromophenyl)dibenzo[b,d]furan

[0088]

[0089] Make 21.2g (100mmol) dibenzo[b,d]furan-4-yl boronic acid, 28.3g (100mmol) 1-bromo-3-iodobenzene, 2.3g (2mmol) tetrakis (triphenylphosphine) palladium, 100ml 2M Na 2 CO 3 A mixture of , 100 ml EtOH and 250 ml toluene was degassed and placed under nitrogen, and then heated at 90° C. overnight. After the reaction was complete, the mixture was cooled to room temperature. The solution was extracted with 500 mL ethyl acetate and 1000 mL water. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (Hx) to give the product 20 g (63%).

[0090] Synthesis of 2-(3-(Dibenzo[b,d]furan-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane alkyl

[0091]

[0092] Make 20g (61.9mmol) 4-(3-bromophenyl) dibenzo[b,d]furan, 19g (75mmol) bis(pinacol radical) diboron, 1.4(1.2mmol) tetrakis(triph...

example 3

[0097] Synthesis of N,N-di-p-tolylspiro[fluorene-9,10'-indeno[1,2-b]triphenylene]-13'-amine

[0098]

[0099] Make 5.5g (10.1mmol) 13'-bromospiro[fluorene-9,10'-indeno[1,2-b]triphenylene], 3g (15.1mmol) di-p-tolylamine, 0.05g (0.2 A mixture of mmol) palladium(II) acetate, 0.15 g (0.4 mmol) 2-(dicyclohexylphosphino)biphenyl, 2 g (20 mmol) sodium tert-butoxide and 100 ml toluene was refluxed overnight under nitrogen. After the reaction was finished, the solution was filtered at 100° C., the filtrate was received, and the filtrate was added to 1 L of MeOH while stirring, and the precipitated product was filtered off under suction. It was recrystallized from toluene to give 4.2 g (63% yield) of yellow product. MS (m / z, FAB + ):661.7

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PUM

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Abstract

The present invention relates to a phenanthro[9,10-b]tetraphenylene derivative and use thereof. The present invention discloses a novel phenanthro[9,10-b]tetraphenylene derivative which is represented by the following formula(I), the organic EL device employing the phenanthro[9,10-b]tetraphenylene derivative as electron blocking material, hole blocking material, electron transport material, phosphorescent host material, or fluorescent host and dopant material can display good performance, wherein L1, L2, Ar1, Ar2, m, p, q and R1 to R3 are the same definition as described in the present invention.

Description

technical field [0001] The present invention generally relates to a novel phenanthrene[9,10-b]tetracene derivative and an organic electroluminescent ( referred to herein as "organic EL") devices. More precisely, the present invention relates to phenanthrene[9,10-b]tetracene derivatives having the general formula (I) and the use of said phenanthrene[9,10-b]tetracene derivatives as An organic EL device that emits a host or a dopant, a hole blocking layer (HBL), an electron blocking layer (EBL), an electron transport layer (ETL), and a hole transport layer (HTL). Background technique [0002] Organic electroluminescence (organic EL) is a type of light emitting diode (LED) in which the emissive layer is a film made of an organic compound that emits light in response to an electric current. An emissive layer of organic compound is sandwiched between two electrodes. Organic EL is used in flat panel displays due to its high illumination, low weight, ultra-thin profile, self-illu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/54C07C209/10C07C13/62C07C2/86C07D333/76C07D307/91C07D471/06C07D251/24C07D239/26C07D219/02C07D209/86C07D279/22C07D403/14C07D403/04C07D403/10C09K11/06H01L51/54
CPCC07C13/72C07C2603/18C07C2603/24C07C2603/42C07C2603/48C07C2603/50C07C2603/54C07C2603/94C07D307/91C09K11/06C07C211/61C07D471/04C07D251/24C07D239/26C07D219/02C07D209/86C07D403/10C07D279/22C07D333/76C07D265/38C07D403/14C07D403/04C09K2211/1018C09K2211/1014C09K2211/1011C09K2211/1007H10K85/615H10K85/622H10K85/624H10K85/626H10K85/636H10K85/633H10K85/654H10K85/657H10K85/6572H10K85/6574H10K85/6576H10K50/11H10K2101/10H10K50/15H10K50/16H10K50/18
Inventor 颜丰文张正澔
Owner NINGBO LUMILAN NEW MATERIAL CO LTD
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