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A kind of organic electroluminescent compound and its preparation method and application

A compound and electroluminescent technology, applied in the fields of organic chemistry, chemical instruments and methods, luminescent materials, etc., can solve the problems of insufficient development of organic electroluminescent materials and backward panel manufacturing enterprises, etc. Effect

Active Publication Date: 2021-03-26
NANJING TOPTO MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] As far as the actual needs of the current organic electroluminescent industry are concerned, the development of organic electroluminescent materials is far from enough, lagging behind the requirements of panel manufacturers

Method used

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  • A kind of organic electroluminescent compound and its preparation method and application
  • A kind of organic electroluminescent compound and its preparation method and application
  • A kind of organic electroluminescent compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Embodiment 1: the synthesis of compound 26

[0067]

[0068] 1) Synthesis of Intermediate 1:

[0069] In a 500ml reaction flask, add 15g (69.4mmol) of 3-bromo-2-pyridinecarboxylic acid methyl ester, add 200ml of tetrahydrofuran and stir to dissolve, add 8.9g (69.4mmol) of 3-thiophene boronic acid, add 3-thiophene boronic acid dissolved in 80ml of water 23.8g (172.5mmol) of potassium carbonate was replaced with nitrogen for 15 minutes, and 0.79g (0.694mmol) of tetrakistriphenylphosphine palladium was added, under nitrogen protection, stirred and heated to 70 degrees, and reacted for 4 hours. Add 100ml of water after the reaction is complete, stir and separate the liquids, wash the organic phase with 150ml of saturated sodium chloride solution, dry the organic phase with anhydrous sodium sulfate, filter, distill under reduced pressure to remove the solvent, and separate and purify by column chromatography to obtain intermediate 1 as 8.4g, yield 55%.

[0070]

[00...

Embodiment 2

[0090] Embodiment 2: the synthesis of compound 58

[0091]

[0092] 1) Synthesis of intermediate 7:

[0093] In a 500ml reaction flask, add 15g (69.4mmol) of 3-bromoisonicotinic acid methyl ester, add 200ml of tetrahydrofuran and stir to dissolve, add 8.9g (69.4mmol) of 3-thiophene boronic acid, add 23.8 g (172.5 mmol) of potassium carbonate, replaced with nitrogen for 15 minutes, added 0.79 g (0.694 mmol) of tetrakistriphenylphosphine palladium, protected by nitrogen, stirred and heated to 70 degrees, and reacted for 4 hours. Add 100ml of water after the reaction is complete, stir and separate the liquids, wash the organic phase with 150ml of saturated sodium chloride solution, dry the organic phase with anhydrous sodium sulfate, filter, distill under reduced pressure to remove the solvent, and separate and purify by column chromatography to obtain intermediate 7 as 8.6 g, yield 61%.

[0094]

[0095] 2) Synthesis of intermediate 8:

[0096] In a 500ml reaction flask...

Embodiment 3

[0114] Embodiment 3: the synthesis of compound 77:

[0115] 1) Synthesis of intermediate 13:

[0116]

[0117] In a 500ml reaction flask, add 20.5g (69.4mmol) of methyl 3,6-dibromopicolinate, add 200ml of tetrahydrofuran and stir to dissolve, add 8.9g (69.4mmol) of 3-thiophene boronic acid, add and dissolve in 80ml 23.8g (172.5mmol) of potassium carbonate in water was replaced with nitrogen for 15 minutes, and 0.79g (0.694mmol) of tetrakistriphenylphosphine palladium was added, under nitrogen protection, stirred and heated to 70°C, and reacted for 4 hours. After the reaction is complete, add 100ml of water, stir and separate the liquids, wash the organic phase with 150ml of saturated sodium chloride solution, dry the organic phase with anhydrous sodium sulfate, filter, distill under reduced pressure to remove the solvent, and separate and purify by column chromatography to obtain intermediate 13 as 7.2 g, yield 35%.

[0118] 2) Synthesis of intermediate 14:

[0119]

...

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Abstract

The invention discloses an organic electroluminescence compound and a preparation method and application thereof. The structural formula of the compound is shown in the description. Y1 and Y2 are C orO or S respectively and independently; X1, X2, X3, X4, X5, X6, X7, X8, X9 and X10 are C or N respectively and independently; R1, R2, R3, R4, R5, R6 and R7 are hydrogen or heavy hydrogen or halogen orCN or Si(CH3)3 or B(OH)2 or alkyl of C1-C40 or alkoxy of C1-C40 or sulfo-alkyl of C1-C40 or naphthenic bases of C3-40 or aryl formed by one or more combinations of aryl and aromatic heterocyclic bases or the compound shown in the description respectively and independently; R8 and R9 are hydrogen or heavy hydrogen or aryl, formed by one or more combinations of aryl and aromatic heterocyclic bases,of C2-C120 respectively and independently. The compound can be applied as an organic electroluminescence material.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to an organic electroluminescent compound and its preparation method and application. Background technique [0002] Organic light-emitting devices (Organic Light-emitting Devices, OLED) are spontaneous light-emitting devices using the following principle: when an electric field is applied, fluorescent substances emit light through the recombination of holes injected from the positive electrode and electrons injected from the negative electrode. This self-luminous device has the characteristics of low voltage, high brightness, wide viewing angle, fast response, good temperature adaptability, etc., and is ultra-thin, and can be fabricated on flexible panels. It is widely used in mobile phones, tablet computers, TVs, lighting, etc. and other fields. [0003] Organic electroluminescent devices are like a sandwich structure, including electrode m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/94C07D405/12C07D405/14C07D491/107C07D491/20C07D495/22C07D495/20C07D409/12C07D333/78C07D495/10C09K11/06H01L51/50H01L51/54
Inventor 许军吕鑫荣
Owner NANJING TOPTO MATERIALS CO LTD
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