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OLED material and application thereof

An independent and unsubstituted technology, applied in the direction of luminescent materials, electrical components, circuits, etc., can solve the problems of difficulty in reaching the deep blue light region, difficulty in achieving high efficiency, and difficulty in mass production and application of materials.

Pending Publication Date: 2021-10-22
BEIJING ETERNAL MATERIAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] This type of material uses carbazole as an electron-donating group, and introduces a large steric hindrance protecting group on the active site of carbazole, which is beneficial to prevent Dexter energy transfer and suppress exciton quenching, but it is difficult to reach the luminescence peak of this type of material In the deep blue light region, it is often difficult to achieve high efficiency for deep blue light devices. In addition, the lifetime of such materials is still short. Due to these factors, it is difficult to realize mass production applications of such materials

Method used

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  • OLED material and application thereof
  • OLED material and application thereof
  • OLED material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0064] Synthesis Example 1: Synthesis of S16

[0065]

[0066] Synthesis of Intermediate S16-1:

[0067] Add 3-deuteromethylcarbazole (50g, 271.36mmol) in a 2000mL three-necked flask, DMF500ml, under nitrogen protection, stir and cool to -20°C with liquid nitrogen ethanol, N-bromosuccinimide (16.98g , 298.5mmol) was dissolved in 100ml of DMF, slowly added dropwise to the reaction solution with a constant pressure dropping funnel, and stirred for 2 hours. Pour the reaction solution into 1000ml of water, extract twice with 1000ml of dichloromethane, combine the organic phases, dry over anhydrous sodium sulfate, filter, spin to dry the solvent, and perform column chromatography on silica gel (PE:DCM=10:1). 69.21 g of white solid was obtained with a yield of 96%. Molecular ion mass determined by mass spectrometry: 263.14 (theoretical: 263.15).

[0068] Synthesis of Intermediate S16-2:

[0069] In a 2000ml three-necked flask, add S16-1 (60g, 228mmol), 4-deuteromethyl-2,3,5,6...

Synthetic example 2

[0072] Synthesis Example 2: Synthesis of S51

[0073]

[0074] Synthesis of Intermediate S51-1:

[0075] In a 2000ml three-necked flask, add 3-bromo-6-deuterocarbazole (50g, 202.34mmol), pentadeuterophenylboronic acid (28.26g, 222.57mmol), tetrakistriphenylphosphine palladium (2.34g, 2.02mmol) Potassium carbonate (55.93g, 404.67mmol), 1,4-dioxane 500ml, water 100ml, replace nitrogen, stir and heat to 110°C, react for 5 hours, stop heating, cool the reaction solution, and use 100 -200 mesh silica gel was filtered, the filtrate was spin-dried, and silica gel sample mixing column chromatography (PE:DCM=10:1) gave 46.86 g of white solid with a yield of 87%. Molecular particle mass determined by mass spectrometry: 265.39 (theoretical value: 265.38).

[0076] Synthesis of compound S51:

[0077] Add S51-1 (40g, 142.13mmol), 2,3,6-trifluorobenzonitrile (7.37g, 46.90mmol), cesium carbonate (69.47g, 212.20mmol), DMF 500ml to replace nitrogen in a 2000ml three-necked flask, Stir a...

Synthetic example 3

[0078] Synthesis Example 3: Synthesis of S91

[0079]

[0080] Synthesis of compound S91:

[0081] Add 3-deutero-tert-butyl-6-deuterocarbazole (41.99g, 179.91mmol) in 2000ml there-necked flask, 2,3,5,6-trifluorobenzonitrile (7g, 39.98mmol), cesium carbonate ( 78.16g, 239.88mmol), DMF 500ml, pumped nitrogen, stirred and heated to 90 ° C, reacted for 12 hours, stopped heating, poured the reaction solution into water, and suction filtered to obtain 45g of white crude product, which was subjected to column chromatography on silica gel ( PE:DCM=10:1), 38.58g of yellow solid was obtained, yield 94%. Molecular particle mass determined by mass spectrometry: 1028.58 (theoretical value: 1028.58).

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Abstract

The invention relates to the technical field of organic electroluminescent materials, in particular to a compound with a structure as shown in a formula (1), wherein X is hydrogen (H) or deuterium (D); and the R1 and R2 are respectively and independently selected from one of hydrogen, cyano, substituted or unsubstituted C1-C12 chain alkyl, substituted or unsubstituted C3-C12 cycloalkyl and substituted or unsubstituted C6-C30 aryl, or respectively and independently represent a structure as shown in a formula Hy-1; and D1 and D2 are each independently a structure as shown in a formula Hy-1. When the compound is used as a luminescent layer material in an OLED device, the compound shows excellent device performance and stability. The invention also protects the organic light-emitting device adopting the compound with the general formula.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent materials, in particular to a compound, a heat-activated delayed fluorescent material, an organic electroluminescent device containing the same and applications thereof. Background technique [0002] Currently, optoelectronic devices using organic materials are becoming more and more popular for a number of reasons. Many of the materials used to make such devices are relatively inexpensive, and optoelectronic devices have a potential cost advantage over inorganic devices. In the structure of organic electroluminescent devices in the field of display and lighting, blue fluorescent materials are generally used together with red and green phosphorescent materials. Recently, it has been reported in the literature that benzonitrile carbazole-based TADF (Thermally Activated Delayed Fluorescence) fluorescent dye compounds are based on benzonitrile as an electron acceptor, and multiple...

Claims

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Application Information

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IPC IPC(8): C07D209/86C07D209/88C07D519/00C09K11/06H01L51/54
CPCC07D209/86C07D209/88C07D519/00C09K11/06C09K2211/1029C09K2211/1007C09K2211/1044C07B2200/05H10K85/6572
Inventor 李熠烺魏金贝李国孟
Owner BEIJING ETERNAL MATERIAL TECH