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Organic compound and application thereof

A technology of compounds and compounds of general formula, applied in the application field of organic electroluminescent devices, can solve the problems of mismatch of electrons and holes in the light-emitting layer, efficiency roll-off, shortening of lifespan, etc.

Inactive Publication Date: 2020-07-07
BEIJING ETERNAL MATERIAL TECH
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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 thereof
  • Organic compound and application thereof
  • Organic compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0046] Synthesis of Compound A1

[0047]

[0048] In the reaction flask, add 29g (100mmol) of 2,4-dichloro-6-phenyltriazine, 22g (110mmol) of 3-(9-phenanthrenyl)phenylboronic acid, 0.9g (0.785 mmol, 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 M1-1.

[0049] In the reaction bottle, add M1-1 18.8g (50mmol), M1-2 16.5g (60mmol), potassium carbonate 21g (150mmol) / DMF200ml, and react at 150°C for 12h. After the reaction is complete, stop the reaction. Water was added to the reaction solution, and a white solid was precipitated. The obtained solid was purified by recrystallization from toluene to obtain A1.

[0050] 1 H NMR (CDCl3, 400MHz) 9.08(s, 1H), 8.84(s, 1H), 8.55(s, 2H), 8.44(s, 1H), 8.37(d, J=8.0Hz, 3H), 8.27(d ,...

Synthetic example 2

[0052] Synthesis of Compound A7

[0053]

[0054] -78°C, add cyanuric chloride (100mmol) to the reaction bottle, and add m-chlorophenylmagnesium bromide (110mmol) dropwise, and react for 5h after the dropwise addition. After the reaction is complete, stop the reaction. Water was added to the reaction solution, extracted with ethyl acetate, and the organic phase was concentrated. The obtained solid was purified by recrystallization from toluene to obtain white powder M2-1.

[0055] In the reaction flask, add 29g (100mmol) of M2-1, 22g (110mmol) of 3-(9-phenanthrenyl)phenylboronic acid, 0.9g (0.785mmol, 0.5%) of tetrakis(triphenylphosphine palladium), 1500ml of toluene, 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 M2-2.

[0056] In the reacti...

Synthetic example 3

[0060] Synthesis of compound A12

[0061]

[0062] In the reaction flask, add 2,4-dichloro-6-(4-biphenyl)triazine 29g (100mmol), 3-phenyl-9-phenanthrenylboronic acid 22g (110mmol), tetrakis(triphenylphosphine palladium ) 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 M3-1.

[0063] In the reaction bottle, add M3-1 18.8g (50mmol), M3-2 16.5g (60mmol), potassium carbonate 21g (150mmol) / DMF200ml, and react at 150°C for 12h. After the reaction is complete, stop the reaction. Water was added to the reaction solution, and a white solid was precipitated. The obtained solid was purified by recrystallization from toluene to obtain A12.

[0064] 1 H NMR (CDCl3, 400MHz) 9.09(d, J=12.0Hz, 2H), 8.74(s, 1H), 8.55(s,...

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Abstract

The invention discloses a compound of general formula (1): wherein X is selected from O, S, NR or CR'R''; the R1 to R3 are independently selected from hydrogen; one of C1-C12 alkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substitutedor unsubstituted C3-C30 heteroaryl is selected from the group consisting of C1-C12 alkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino; the a is 0, 1 or 2; the L1 to L3 are each independently selected from one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; and the Ar is one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group. When the compound provided by the invention is used as a luminescent material in an OLED device, excellent device performance and stability are shown. The invention also discloses an organic light-emitting device adopting the compound with the general formula.

Description

technical field [0001] The invention relates to an 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, etc. Compared with liquid crystal display, organic electroluminescent display is not It needs a backlight source, has a large viewing angle, low power, and its response speed can reach 1000 times that of a liquid crystal display, but its manufacturing cost is lower than that of a liquid crystal display with the same resolution. Therefore, organic electroluminescent devices have broad application prospects. [0003] With the continuous advancement of OLED technology in the two major fields of lighting and display, people pay m...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07D487/14C07D403/04C07D495/04C07D491/048C09K11/06H01L51/50H01L51/54
CPCC07D487/04C07D487/14C07D403/04C07D495/04C07D491/048C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1059C09K2211/1088C09K2211/1092H10K85/615H10K85/626H10K85/6576H10K85/657H10K85/6574H10K85/6572H10K50/11
Inventor 邢其锋曾礼昌李之洋任雪艳
Owner BEIJING ETERNAL MATERIAL TECH