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Heteroatom-containing spiro organic electroluminescent compound as well as preparation method and application thereof

A heteroatom, electroluminescence technology, applied in the direction of silicon organic compounds, organic chemistry, compounds of elements of group 4/14 of the periodic table, etc., can solve the problems of device deterioration and low amorphousness

Active Publication Date: 2021-02-12
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Materials with low amorphousness, even in a short period of time, allow their thin films to crystallize, and thus degrade the device

Method used

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  • Heteroatom-containing spiro organic electroluminescent compound as well as preparation method and application thereof
  • Heteroatom-containing spiro organic electroluminescent compound as well as preparation method and application thereof
  • Heteroatom-containing spiro organic electroluminescent compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0130] Embodiment 1: preparation compound ET-2

[0131]

[0132] 1. Under nitrogen protection, dissolve raw material D2-2 (30.00mmol) and raw material B3-2 (30.00mmol) in 150.00ml of toluene, ethanol and water (V toluene: V ethanol: V water = 3:1:1) Add tetrakistriphenylphosphine palladium (0.3mmol) and potassium carbonate (60.00mmol) to the mixed solution, stir evenly, heat up to 90°C, and reflux for 5 hours, after the solution is cooled to room temperature, keep the organic phase, and then use The aqueous phase was extracted with ethyl acetate; after combining the organic phases, they were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain solid organic matter; the solid organic matter was completely dissolved with dichloromethane, and then slowly added dropwise to petroleum ether In the solution, stir evenly, there is precipitation, and the solid is obtained by suction filtration, rinsed with absolute ethanol and petro...

Embodiment 2

[0145] Embodiment 2: preparation compound ET-29

[0146]

[0147] 1. Under nitrogen protection, dissolve raw material A2-29 (30.00mmol) and raw material B2-29 (30.00mmol) in 200.00ml of toluene, ethanol and water (V toluene: V ethanol: V water = 3:1:1) Add tetrakistriphenylphosphine palladium (0.30mmol) and potassium carbonate (60.00mmol) to the mixed solution, stir evenly, heat up to 90°C, and reflux for 5 hours, after the solution is cooled to room temperature, keep the organic phase, and then use The aqueous phase was extracted with ethyl acetate; after combining the organic phases, they were dried using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain solid organic matter. Use dichloromethane to completely dissolve the solid organic matter, then slowly add it dropwise into the petroleum ether solution, stir evenly, there is precipitation, and the solid is obtained by suction filtration, rinsed with absolute ethanol and petrole...

Embodiment 3

[0160] Embodiment 3: preparation compound ET-37

[0161]

[0162] 1. Under nitrogen protection, dissolve raw material A1-37 (30.00mmol) and raw material B1-37 (30.00mmol) in 170.00ml of toluene, ethanol and water (V toluene: V ethanol: V water = 3:1:1) Add tetrakistriphenylphosphine palladium (0.30mmol) and potassium carbonate (60.00mmol) to the mixed solution, stir evenly, heat up to 90°C, and reflux for 5 hours, after the solution is cooled to room temperature, keep the organic phase, and then use The aqueous phase was extracted with ethyl acetate; after combining the organic phases, they were dried using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain solid organic matter. Use dichloromethane to completely dissolve the solid organic matter, then slowly add it dropwise into the petroleum ether solution, stir evenly, there is precipitation, and the solid is obtained by suction filtration, rinsed with absolute ethanol and petrole...

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Abstract

The invention relates to a heteroatom-containing spiro organic electroluminescent compound as well as a preparation method and the application thereof. The structural formulas of the heteroatom-containing spiro organic electroluminescent compound are shown as a chemical formula 1 and a chemical formula 2, wherein m, n and p in the chemical formula 1 are 0 or 1; x independently represents a connecting bond, -O-, -S-, -SO2-, -C(R3)(R4)-, -N(R5)-, -Si(R6)(R7)-, -Sn(R8)(R9)-, and -Ge(R10) (R11); L1, L2 and L3 are link bonds, C6C30 arylene groups and ternary 15-membered heteroarylene groups; wherein R1 and R2 are the same or different from each other and are respectively and independently hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, amino, silicon base and borane; Ar1-Ar4 each independently represents a C3-C30 cycloalkyl group and a ternary 20-membered heterocycloalkyl group, and an electron injection layer and / or an electron transport layer of an organic light-emitting device prepared from the compound can significantly improve the electron transport efficiency from the electron transport layer to a light-emitting layer, thereby improving the light-emitting efficiency.

Description

technical field [0001] The invention relates to the technical field of luminescent materials, in particular to a heteroatom-containing spiro-ring organic electroluminescence compound and a preparation method and application thereof. Background technique [0002] Organic EL devices are self-luminous devices, and are recognized by the industry as one of the most promising flat panel display technologies that may replace liquid crystals in the future. It has higher luminance and higher visibility than liquid crystal devices, enables clear display, and thus has been actively researched. [0003] So far, many improvements have been made to put organic EL devices into practical use. For example, it is generally well known that high efficiency and durability can be achieved by a multi-layer structure (i.e., having an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, an electron transport layer, and a cathode on a substrate)...

Claims

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Application Information

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IPC IPC(8): C07D405/04C07D405/10C07D405/14C07D409/04C07D409/10C07D409/14C07F7/08C09K11/06H01L51/50H01L51/54
CPCC07D405/04C07D405/10C07D405/14C07D409/04C07D409/10C07D409/14C07F7/0816C07F7/083C09K11/06C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/1092C09K2211/1096H10K85/615H10K85/654H10K85/6574H10K85/6576H10K85/40H10K85/6572H10K50/16H10K50/171
Inventor 汪康王进政黄悦王永光王士凯金成寿马晓宇
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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