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Organic compound and application of organic compound in organic electroluminescent device

A technology of organic compounds and compounds, applied in organic chemistry, electrical solid-state devices, electrical components, etc., can solve problems such as mismatch between electrons and holes in the light-emitting layer, shortened lifespan, and efficiency roll-off

Pending Publication Date: 2019-10-11
BEIJING ETERNAL MATERIAL TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The single carrier transport capability will cause a mismatch of electrons and holes in the light-emitting layer, resulting in severe efficiency roll-off and shortened lifetime

Method used

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  • Organic compound and application of organic compound in organic electroluminescent device
  • Organic compound and application of organic compound in organic electroluminescent device
  • Organic compound and application of organic compound in organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0069] Synthesis Example 1: Synthesis of Compound A1

[0070]

[0071] In the reaction flask, add 21.8g (100mmol) of 2-methylthio-1-naphthaleneboronic acid, 16.5g (110mmol) of bromobenzene, 0.9g (0.785mmol, 0.5%) of tetrakis(triphenylphosphine palladium), 1500ml toluene, ethanol 1000ml, potassium carbonate 43.3g (314 mmol) / water 1000ml, react at 80°C for 3.5h. After the reaction is complete, stop the reaction. After cooling to room temperature and filtering, the obtained solid was purified by recrystallization from toluene to obtain white powder M1.

[0072] Intermediate M132.4g (100mmol) was dissolved in 150ml of glacial acetic acid, 30% hydrogen peroxide (5ml) was added in ice bath at 0°C, reacted at room temperature for 10h, after stopping the reaction, extracted, dried, evaporated the solvent, and the column layer Separated by analysis, a white solid M2 was obtained.

[0073] Intermediate M2 26.9g (100mmol) and phosphorus pentoxide (10mmol) were added to 20ml of tr...

Synthetic example 2

[0078] Synthesis of Synthesis Example 2 Compound A8

[0079]

[0080] In the reaction flask, add 25.2g (100mmol) of 1-methylthio-2-naphthaleneboronic acid-7-chloro, 30.6g (110mmol) of m-bromoiodobenzene, 0.9g (0.785mmol, 0.5% ), toluene 1500ml, ethanol 1000ml, potassium carbonate 43.3g (314mmol) / water 1000ml, react at 80°C for 3.5h. After the reaction is complete, stop the reaction. After cooling to room temperature and filtering, the obtained solid was purified by recrystallization from toluene to obtain white powder M1.

[0081] 36.3g (100mmol) of intermediate M1 was dissolved in 150ml of glacial acetic acid, 30% hydrogen peroxide (5ml) was added in ice bath at 0°C, and reacted at room temperature for 10h. After stopping the reaction, extracted, dried, evaporated the solvent, and the column layer Separated by analysis, a white solid M2 was obtained.

[0082] Intermediate M2 37.9g ​​(100mmol) and phosphorus pentoxide (10mmol) were added to 20ml of trifluoromethanesulfon...

Synthetic example 3

[0085] Synthesis Example 3: Synthesis of Compound A19

[0086]

[0087] In the reaction flask, add 21.8g (100mmol) of 2-methylthio-1-naphthaleneboronic acid, 16.5g (110mmol) of bromobenzene, 0.9g (0.785mmol, 0.5%) of tetrakis(triphenylphosphine palladium), 1500ml toluene, ethanol 1000ml, potassium carbonate 43.3g (314 mmol) / water 1000ml, react at 80°C for 3.5h. After the reaction is complete, stop the reaction. After cooling to room temperature and filtering, the obtained solid was purified by recrystallization from toluene to obtain white powder M1.

[0088] 32.4g (100mmol) of intermediate M1 was dissolved in 150ml of glacial acetic acid, and 30% hydrogen peroxide (5ml) was added in an ice bath at 0°C, and reacted at room temperature for 10h. After the reaction was stopped, extraction, drying, evaporation of solvent, and column layer Separated by analysis, a white solid M2 was obtained.

[0089] Intermediate M2 26.9g (100mmol) and phosphorus pentoxide (10mmol) were ad...

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Abstract

The invention provides a compound and an organic electroluminescent device using the compound. The compound is expressed by a general formula (I) shown in the description, wherein X is O, S or Se; Ar1and Ar2 are respectively and independently selected from C6-C30 aryls, C3-C30 heteroaryls and A, and at least one of the Ar1 and the Ar2 is a heteroaryl; L1 and L2 are respectively and independentlyselected from a single bond, C6-C30 arylidenes and C3-C30 sub-heteroaryls; R1 and R2 are respectively and independently selected from hydrogen, C1-C12 alkyls or naphthenic bases, the C6-C30 aryls andthe C3-C30 heteroaryls, and the adjacent R1 and R2 can be connected into a ring; p and q are respectively 1-4 integers; m and n are respectively 0-4 integers; Ar3 and Ar4 are respectively and independently selected from the C6-C30 aryls and the C3-C30 heteroaryls; and when above various groups have substituent groups, the substituent groups are the aryls or the heteroaryls.

Description

technical field [0001] The invention relates to a novel organic compound, in particular to a compound used in an organic electroluminescent device and its application in the organic electroluminescent device. Background technique [0002] Organic electroluminescent display (hereinafter referred to as OLED) has a series of advantages such as self-luminescence, low-voltage DC drive, full curing, wide viewing angle, light weight, simple composition and process, and has broad application prospects. [0003] With the continuous advancement of OLED technology in the two major fields of lighting and display, people are paying more attention to the research of high-efficiency organic materials that affect the performance of OLED devices. Currently used phosphorescent host materials often have a single carrier transport capability, such as hole transport hosts and electron transport hosts. The single carrier transport ability will cause a mismatch of electrons and holes in the light...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/04C07D409/04C07D409/14C07D519/00C07D421/14C07D471/04C07D491/048C07D491/147C07D495/04C07D495/14C09K11/06H01L51/54
CPCC07D409/04C07D495/04C07D495/14C07D491/048C07D519/00C07D421/14C07D471/04C07D409/14C07D405/04C07D491/147C09K11/06C09K2211/1092C09K2211/1044C09K2211/1029C09K2211/1074C09K2211/1088C09K2211/1007C09K2211/1014C09K2211/1011C09K2211/1096H10K85/636H10K85/626H10K85/633H10K85/631H10K85/615H10K85/654H10K85/6576H10K85/6574H10K85/657H10K85/6572
Inventor 邢其锋李之洋黄鑫鑫邵爽
Owner BEIJING ETERNAL MATERIAL TECH
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