Hole organic electroluminescent compound as well as preparation method and application thereof

A compound and luminescence technology, which is applied in the preparation of organic compounds, amino compounds, organic chemistry, etc., can solve the problems of low driving voltage and unsatisfactory life, and achieve life extension, maximum external quantum efficiency improvement, drive The effect of voltage reduction

Inactive Publication Date: 2020-12-11
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The first object of the present invention is to provide a kind of organic electroluminescent compound of hole type, to solve the technical problem that the service life of existing organic electroluminescent device is not ideal, the device prepared by adopting the compound of the present invention has excellent current efficiency and relatively Low driving voltage and long service life

Method used

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  • Hole organic electroluminescent compound as well as preparation method and application thereof
  • Hole organic electroluminescent compound as well as preparation method and application thereof
  • Hole organic electroluminescent compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Embodiment 1: preparation compound H-006

[0059] synthetic route:

[0060]

[0061] Specific synthesis method:

[0062] Step 1. Under nitrogen protection, dissolve raw material A-006 (11.31g, 20.00mmol) and raw material E-006 (7.71g, 20.00mmol) in 180.00ml of toluene solution, add tris(dibenzylideneacetone) di Palladium (0.18g, 0.20mmol), tri-tert-butylphosphine (0.20g, 1.00mmol) and sodium tert-butoxide (3.84g, 40.00mmol), stir evenly, heat up to 90°C, and reflux for 5h; after the reaction , slightly lower the temperature to 70°C, filter with diatomaceous earth to remove salt and catalyst, wash the filtrate three times with water after cooling to room temperature, keep the organic phase, then extract the aqueous phase with ethyl acetate; after combining the organic phase, use Magnesium sulfate water was dried, and the solvent was removed using a rotary evaporator; using dichloromethane and petroleum ether (V 二氯甲烷 :V 石油醚 =10:4) was purified by column chromatogra...

Embodiment 2

[0069] Embodiment 2: preparation compound H-048

[0070] synthetic route:

[0071]

[0072] Specific synthesis method:

[0073] Step 1, under nitrogen protection, raw material A (9.49g, 20mmol) and raw material B (5.54g, 20mmol) were dissolved in 150.00ml toluene, ethanol and water (V 甲苯 :V 乙醇 :V 水 =3:1:1) into the mixed solution, add tetrakis triphenylphosphine palladium (0.23g, 0.20mmol) and potassium carbonate (5.53g, 40.00mmol), stir well, heat up to 90°C, and reflux for 5 hours, After the solution was cooled to room temperature, the organic phase was retained, and then the aqueous phase was extracted with ethyl acetate; after the organic phases were combined, they were dried using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain solid organic matter. Use about 100ml of dichloromethane to completely dissolve the solid organic matter, then slowly add it dropwise into the petroleum ether solution, stir evenly, and a precipit...

Embodiment 3

[0081] Embodiment 3: preparation compound H-052

[0082] synthetic route:

[0083]

[0084]

[0085] Specific synthesis method:

[0086] Step 1, under nitrogen protection, raw material A-052 (14.29g, 30.00mmol) and raw material B-052 (6.02g, 30.00mmol) were dissolved in 200.00ml toluene, ethanol and water (V 甲苯 :V 乙醇 :V 水 =3:1:1) in the mixed solution, add tetrakis triphenylphosphine palladium (0.35g, 0.30mmol) and potassium carbonate (8.29g, 60.00mmol), stir well, heat up to 90°C, and reflux for 5 hours, After the solution was cooled to room temperature, the organic phase was retained, and then the aqueous phase was extracted with ethyl acetate; after the organic phases were combined, they were dried using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain solid organic matter. Use 100ml of dichloromethane to completely dissolve the solid organic matter, then slowly add it dropwise into the petroleum ether solution, stir eve...

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Abstract

The invention relates to a hole organic electroluminescent compound as well as a preparation method and application thereof; the compound has the structural formula defined in the specification, wherein m and n are integers from 0 to 1 and are not 0 at the same time; the ring A and the ring B are adamantane and do not exist at the same time; X and Y independently represent a connection bond, -O-,-S-, -C(R3)(R4), -N(R5)-, -Si(R6)(R7)-, and at most one of X and Y is a connection bond; R1 and R2 are the same or different from each other, and are each independently hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, amino, sulfonic acid group, sulfonyl, phosphate group, phosphoryl, silicon group and borane group; L1 and L2 are a link bond, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted three-membered-10-membered heteroaryl group; and R3, R4, R5, R6, R7, R8, R9, R10 and R11 are the same as or different from each other and are each independently a substituted or unsubstituted C1-C10 alkyl group. A device prepared from the compound provided by the invention has excellent current efficiency, low driving voltage and long service life.

Description

technical field [0001] The invention relates to the technical field of luminescent materials, in particular to a hole-type organic electroluminescent compound and its preparation method and application. Background technique [0002] The organic electroluminescence element is a self-luminous element utilizing the principle that a fluorescent substance emits light by recombination energy of holes injected from the anode and electrons injected from the cathode by applying an electric field. It has the following structure: an anode, a cathode, and a layer of organic material in between. In order to improve the efficiency and stability of organic electroluminescent elements, the organic material layer usually includes multiple layers with different materials, such as hole injection layer (HIL), hole transport layer (HTL), light emitting layer, electron transport layer (ETL ) and electron injection layer (EIL). In this organic light-emitting element, when a voltage is applied be...

Claims

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Application Information

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IPC IPC(8): C07D335/04C07D409/12C07D409/14C07D311/78C07D407/12C07D405/14C07D405/04C07D213/38C07D333/76C07D307/91C07C211/61C07C209/00C07D307/77C07D409/10C09K11/06H01L51/50H01L51/54
CPCC07D335/04C07D409/12C07D409/14C07D311/78C07D407/12C07D405/14C07D405/04C07D213/38C07D333/76C07D307/91C07C211/61C07C209/00C07D307/77C07D409/10C09K11/06C07C2603/90C09K2211/1029C09K2211/1088C09K2211/1092H10K85/624H10K85/615H10K85/636H10K85/633H10K85/6576H10K85/6574H10K85/6572H10K50/15
Inventor 王进政张鹤李贺曹淼杨冰白金凤马晓宇
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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