Pyrene compound containing benzo cyclohexyl alkane structure and organic light emitting device

A technology of benzocyclohexane and organic light-emitting devices, which is applied in the preparation of amino compounds from amines, light-emitting materials, organic chemistry, etc., can solve the problems of not meeting the requirements of long-life dark blue light-emitting compounds, and reduce the interaction , Improve luminous efficiency, increase the effect of steric hindrance

Inactive Publication Date: 2019-04-26
AAC TECH NANJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Although a large number of patents and documents have carried out a lot of research on pyrene compounds, the existing research is far from meeting the requirements for long-life deep blue light-emitting compounds.

Method used

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  • Pyrene compound containing benzo cyclohexyl alkane structure and organic light emitting device
  • Pyrene compound containing benzo cyclohexyl alkane structure and organic light emitting device
  • Pyrene compound containing benzo cyclohexyl alkane structure and organic light emitting device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0098] Compound FBD-3

[0099]

[0100] Synthesis Step 1: Synthesis of Intermediate 1:

[0101]

[0102] Into a 75ml three-neck flask, sequentially add 30ml of toluene, 2.0g of 1-aminotetralin, 1.70g of 2,5-dimethylbromobenzene, 1.74g of sodium tert-butoxide, and 0.14g of tris(dibenzylideneacetone)palladium , 2-cyclohexylphosphine-2,6-methoxy-1,1-biphenyl 0.18g, after nitrogen replacement three times, the system was heated up to 85 degrees, and kept for 12 hours, the system was directly shrunk to dryness after cooling down, and the column layer Analysis, dichloromethane (DCM): petroleum ether (PE) = 1:10, 2.07 g of yellow solid was obtained. Yield 90%.

[0103] Synthesis Step 2: Synthesis of Compound FBD-3:

[0104]

[0105] Add 0.96 g of 1,6-dibromopyrene, 2.0 g of intermediate 3, 200 mg of palladium acetate, 5 ml of tri-tert-butylphosphine, 960 mg of sodium tert-butoxide, and 50 ml of toluene into a 100 ml three-necked flask. 85°C, heat preservation for 12h, the...

Embodiment 2

[0110] Compound FBD-O-5

[0111]

[0112] Synthesis Step 1: Synthesis of Intermediate 2

[0113]

[0114] Into a 75ml three-necked flask, add 30ml of toluene, 2.7g of 1-aminotetralin, 2.25g of 4-bromodibenzofuran, 2.2g of sodium tert-butoxide, 0.18g of tris(dibenzylideneacetone) palladium, 2 -Cyclohexylphosphine-2,6-methoxy-1,1-biphenyl 0.22g, after nitrogen replacement three times, the temperature of the system was raised to 85 degrees, and the reaction was kept for 12 hours, and the system was directly shrunk to dryness after cooling down, and column chromatography Dichloromethane (DCM): petroleum ether (PE) = 1:20 to obtain 2.28 g of a yellow solid. Yield 91%.

[0115] Synthesis Step 2: Synthesis of Compound FBD-O-5:

[0116]

[0117] Add 1.1g of 1,6-dibromopyrene, 2.2g of intermediate 2, 220mg of palladium acetate, 5ml of tri-tert-butylphosphine, 1.0g of sodium tert-butoxide, and 50ml of toluene into a 100ml three-necked flask. Heat at 85°C and keep warm for 1...

Embodiment 3

[0121] Compound FBD-P-1.

[0122]

[0123] Synthetic Step 1: Synthesis of Intermediate 3

[0124]

[0125] Into a 75ml three-necked flask, sequentially add 30ml of toluene, 2.7g of 1-aminotetralin, 2.12g of 3-bromobiphenyl, 2.2g of sodium tert-butoxide, 0.18g of tris(dibenzylideneacetone)palladium, 2-cyclo Hexylphosphine-2,6-methoxy-1,1-biphenyl 0.22g, nitrogen replacement three times, the system was heated up to 90 degrees, heat preservation reaction for 12 hours, the system was directly shrunk to dryness after cooling down, column chromatography, DCM: PE=1:10, 2.34 g of yellow solid was obtained. Yield 87%.

[0126] Synthesis Step 2: Synthesis of Compound FBD-P-1

[0127]

[0128] Add 1.1g of 1,6-dibromopyrene, 2.1g of intermediate 3, 220mg of palladium acetate, 5ml of tri-tert-butylphosphine, 1.0g of sodium tert-butoxide, and 50ml of toluene into a 100ml three-necked flask. Heat at 85°C and keep warm for 12 hours. After the system is concentrated, column chroma...

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PUM

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Abstract

The invention provides a pyrene compound containing a benzo cyclohexyl alkane structure. The structural general formula of the pyrene compound is shown in formula (I) as shown in specification. The invention further provides an organic light emitting device. According to the pyrene compound containing the benzo cyclohexyl alkane structure, non-conjugated cyclohexane is introduced by ring fusion, thus, the steric hindrance of molecules is improved, and intermolecular interaction is relieved; and meanwhile, other introduced aromatic rings or aromatic heterocyclic rings do not contain condensed ring structures, and thus are not easily affected by the environment of the outside, the emission spectrum of the compound is dark blue, the spectrum seldom changes in different environments, the service life is prolonged, and the requirement of a long-service-life dark blue light emitting compound is met.

Description

【Technical field】 [0001] The invention relates to the field of organic photoelectric materials, in particular to a pyrene compound containing a benzocyclohexane hydrocarbon structure and an organic light-emitting device. 【Background technique】 [0002] With the development of science and technology, people pay more and more attention to the use of organic materials to prepare various organic electronic devices, especially for functional devices with photoelectric response, such as common organic electroluminescence devices, organic solar cell devices, organic field effect transistor devices and Organic photosensitive sensor devices. [0003] Organic electroluminescent device is a device technology that realizes electroluminescence by introducing one or more layers of organic films on the cathode and anode. It can achieve ultra-thin, flexible and transparent performance, and is used in flat panel display and lighting industries. increase year by year. [0004] For organic l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/61C07C209/68C07D319/24C07D333/76C07D307/91C09K11/06H01L51/54
CPCC09K11/06C07C211/61C07D307/91C07D319/24C07D333/76C09K2211/1092C09K2211/1088C09K2211/1007H10K85/60H10K85/622H10K85/653H10K85/636H10K85/633H10K85/655H10K85/615
Inventor 马腾达黄达
Owner AAC TECH NANJING
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