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Compound taking quinolinone derivative as core and application of compound in organic electroluminescent device

A compound and derivative technology, applied in the application field of organic electroluminescent devices, can solve problems such as performance differences

Active Publication Date: 2020-04-07
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.

Method used

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  • Compound taking quinolinone derivative as core and application of compound in organic electroluminescent device
  • Compound taking quinolinone derivative as core and application of compound in organic electroluminescent device
  • Compound taking quinolinone derivative as core and application of compound in organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0067] Preparation of Intermediate B:

[0068] Preparation of Intermediate I-1:

[0069]

[0070] (1) 500mL three-necked flask, under nitrogen protection, add 0.05mol raw material C-1, 0.06mol raw material D-1, dissolve with mixed solvent (180ml toluene, 90ml ethanol), then add 0.15mol Na 2 CO 3 Aqueous solution (2M), stirred with nitrogen for 1 hour, then added 0.0005mol Pd (PPh 3 ) 4 , 100 ℃ heating reflux for 15 hours, sampling point plate, the reaction is complete. Naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain intermediate L-1 with HPLC purity of 93.4% and yield of 64.2%.

[0071] Elemental analysis structure (molecular formula C 23 H 17 BrS 2 ): Theoretical C, 63.16; H, 3.92; Br, 18.27; S, 14.66; Tested: C, 63.15; H, 3.92; Br, 18.27; S, 14.67. ESI-MS (m / z) (M+): theoretical value 436.00, found value 436.12.

[0072] (2) Under nitrogen protection, weigh 0.01 mol of intermediate L-1 and 0.012 mol...

Embodiment 1

[0104] Example 1: Synthesis of Compound 2:

[0105]

[0106] In a 250mL three-necked flask, nitrogen was introduced, 0.01mol of raw material A-1 and 0.015mol of Intermediate I-1 were added, dissolved in a mixed solvent of toluene and ethanol (90mL of toluene and 45mL of ethanol), and then 0.03mol of Na was added. 2 CO 3 Aqueous solution (2M), stirred with nitrogen for 1h, then added 0.0001mol Pd (PPh 3 ) 4 , 100 ℃ heating under reflux for 15h, sampling point plate, the reaction is complete. Natural cooling, filtration, rotary evaporation of the filtrate, and passage of the residue through a silica gel column to obtain the target product with a purity of 98.1% and a yield of 84.9%. Elemental analysis structure (molecular formula C 52 H 36 N 2 OS): Theoretical C, 84.75; H, 4.92; N, 3.80; O, 2.17; S, 4.35; Tested: C, 84.75; H, 4.91; N, 3.82; O, 2.17; ESI-MS (m / z) (M+): Theoretical value is 736.25, and the found value is 736.19.

Embodiment 2

[0107] Example 2: Synthesis of Compound 12:

[0108]

[0109] The preparation method of compound 12 is the same as that of Example 1, except that the starting material A-2 is used to replace the starting material A-1, and the intermediate II-1 is used to replace the intermediate I-1. Elemental analysis structure (molecular formula C 51 H 36 N 4 O): theoretical C, 84.97; H, 5.03; N, 7.77; O, 2.22; found: C, 84.96; H, 5.03; N, 7.77; O, 2.23. HPLC-MS: The molecular weight of the material is 720.29, and the measured molecular weight is 720.35.

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Abstract

The invention discloses a compound taking a quinolinone derivative as a core and an application of the compound in an organic electroluminescent device. The compound structurally contains the quinolinone derivative as an electron acceptor, so that transmission of electrons in a light-emitting layer is facilitated. A connected heterocyclic group is an electron donor, so as to facilitate the transmission of holes in the light-emitting layer. Nitrogen atoms in the heteroatom-containing benzoazadione are saturated atoms, have quite strong rigidity and are beneficial to improving the triplet stateenergy level of the parent nucleus compound, and the combination of the electron donor and the electron acceptor can improve the recombination efficiency of excitons, the starting voltage is reduced and the performance of the device is improved. When the compound is used as a light-emitting layer material of the organic electroluminescent device, the current efficiency of the device is greatly improved, and the service life of the device is obviously prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound with a quinolinone derivative as the core and its application in an organic electroluminescence device. Background technique [0002] At present, OLED display technology has been applied in smart phones, tablet computers and other fields, and will be further expanded to large-scale application fields such as TVs. However, compared with the actual product application requirements, the luminous efficiency and service life of OLED devices. Further improvement is needed. [0003] The current research on improving the performance of OLED light-emitting devices includes: reducing the driving voltage of the device, improving the luminous efficiency of the device, and improving the service life of the device. In order to realize the continuous improvement of the performance of OLED devices, it is not only necessary to innovate the structure and production process of OL...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07D519/00C07D491/048C07D495/04C07D517/04C07D401/10C07D409/10C07D405/10C07D421/10C07D487/04C09K11/06H01L51/50H01L51/54
CPCC07D471/04C07D519/00C07D491/048C07D495/04C07D517/04C07D401/10C07D409/10C07D405/10C07D421/10C07D487/04C09K11/06C09K2211/1029C09K2211/1007C09K2211/1088C09K2211/1092C09K2211/1096H10K85/657H10K85/6576H10K85/6574H10K85/6572H10K50/11
Inventor 庞羽佳叶中华李崇王芳
Owner JIANGSU SUNERA TECH CO LTD
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