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Green-light narrow-spectrum three-coordinate boron luminous compound, luminous composition and application thereof

A compound, narrow spectrum technology, applied in the green light narrow spectrum tri-coordinated boron luminescent compound, the application field of organic electroluminescent devices, can solve the problem of lack of high-performance green luminescent materials and so on

Inactive Publication Date: 2019-12-31
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The problem to be solved by the present invention is that there is a lack of high-performance green light-emitting materials in the existing narrow-spectrum TADF material system, and a green-light narrow-spectrum tricoordinate boron light-emitting compound containing a carbazole skeleton, a light-emitting composition and its application are provided

Method used

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  • Green-light narrow-spectrum three-coordinate boron luminous compound, luminous composition and application thereof
  • Green-light narrow-spectrum three-coordinate boron luminous compound, luminous composition and application thereof
  • Green-light narrow-spectrum three-coordinate boron luminous compound, luminous composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0100] Table 1. Summary of Synthesis Example Product Data.

[0101]

[0102] In the first step, 60 mL of an anhydrous solution containing 35.2 mmol of raw materials (ie, 3,6-bis(4-(tert-butyl)phenyl)-9H-carbazole or its derivatives: C-1 to C-6) DMF (N, N-dimethylformamide) solution was slowly added dropwise to 50 mL of anhydrous DMF solution containing 4.9 g of potassium tert-butoxide (43.8 mmol), and after stirring at room temperature for 2 hours, 20 mL of 3. 1 g of 2-bromo-1,3-difluorobenzene (16.0 mmol) in dry DMF. The reaction system was stirred at 140° C. for 24 hours, then cooled to room temperature, and poured into ice water (2 L). The white solid was filtered off with suction, dried in vacuo, and further purified by column chromatography using a mixed eluent of dichloromethane / petroleum ether to afford intermediate 1a as a white solid.

[0103] In the second step, under the protection of nitrogen atmosphere, 19.4 mL of n-hexane solution (25.2 mmol) of tert-butylli...

Embodiment 2

[0107] Table 2. Summary of Synthesis Example Product Data.

[0108]

[0109]

[0110]

[0111] In the first step, 4.1g 3,5-difluoro-4-chlorobromobenzene (18mmol), 19.8mmol organic boric acid raw material (B1-B28), 5.0g potassium carbonate (36mmol), 1g tetrakis (triphenylphosphine ) palladium (0.9mmol), add 144mL tetrahydrofuran and 36mL water, the system is repeatedly evacuated and filled with nitrogen three times, then heated to reflux under the protection of nitrogen for 24 hours, cooled to room temperature, the reaction solution was filtered, and 0.5L water was added to the filtrate , the organic phase was extracted three times with 1L of dichloromethane in equal parts, the organic phase was separated and concentrated in vacuo, and then further purified by column chromatography using a mixed eluent of dichloromethane / petroleum ether to obtain a white solid 2a.

[0112] In the second step, 60 mL of anhydrous DMF containing 35.2 mmol of raw material (3,6-bis(4-(tert-...

Embodiment 3

[0118] Table 3. Synthesis Example Product Data Summary

[0119]

[0120]

[0121]

[0122]

[0123]

[0124] In the first step, 4.1g 3,5-difluoro-4-chlorobromobenzene (18mmol), 19.8mmol raw organic aromatic amine (A1-A54), 19.0g sodium tert-butoxide (19.8mmol), 330mg tris(di Benzylideneacetone) dipalladium (0.36mmol) and 182mg tri-tert-butylphosphine (0.9mmol) were added to 90mL toluene, the system was repeatedly evacuated and filled with nitrogen three times, then heated to reflux for 24 hours under the protection of nitrogen, and then cooled to room temperature , filter the reaction solution, add 0.5L water to the filtrate, divide and extract the organic phase three times with 1L dichloromethane in equal amounts, separate the organic phase and concentrate in vacuo, then use the mixed eluent of dichloromethane / petroleum ether Further purification by column chromatography afforded intermediate 3a as a white solid.

[0125] In the second step, 60 mL of anhydrous...

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Abstract

Belonging to the technical field of organic electroluminescence, the invention discloses a green-light narrow-spectrum three-coordinate boron luminous compound, a luminous composition and applicationthereof in organic light-emitting devices. The luminous compound disclosed by the invention is shown as formula (I) in the specification, and has TADF (thermally activated delayed fluorescence) luminous characteristic. The luminous composition is composed of a compound (with a weight percentage content of 0.3-5.0%) shown as formula (I), a derivative formed by 2-3 carbazole groups and a derivativeformed by 1-2 1, 3, 5-triazine groups. The luminous compound and the luminous composition prepared according to the invention can be used as luminescent materials to construct luminescent layers of organic light-emitting devices, and the organic light-emitting devices can be applied to preparation of organic light-emitting displays or organic light-emitting lighting sources.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence, and in particular relates to a green-light narrow-spectrum tricoordinate boron luminescent compound, a luminescent composition and its application in organic electroluminescent devices. Background technique [0002] In the early 1960s, Pope et al. first reported the phenomenon of organic electroluminescence. When they applied a high voltage of 400 volts on both sides of anthracene single crystal, they observed the blue light emitted by anthracene (see M.Pope, H.Kallmann and P. Magnante, J. Chem. Phys., 1963, 38, 2042). However, due to the difficulty of growing single crystals and the high driving voltage of the device, the process they used has little practical use. Until 1987, C.W.Tang et al. of Kodak Corporation of the United States used ultra-thin film technology to use aromatic amines with better hole transport effects as the hole transport layer, aluminum complexes of 8-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/50H01L51/54
CPCC07F5/027C07F5/02C09K11/06C09K2211/1014C09K2211/1055C09K2211/1033C09K2211/1037C09K2211/1029C09K2211/1088C09K2211/1092H10K85/322H10K50/11
Inventor 王悦
Owner JILIN UNIV
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