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Indolocarbazole derivative and application thereof to electroluminescent device

An electroluminescent device, indolocarbazole technology, applied in the field of indolocarbazole derivatives and their application in electroluminescent devices

Active Publication Date: 2013-08-14
JILIN YUANHE ELECTRONICS MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] But in actual use, there are still many shortcomings that need to be improved, which requires the design of new materials to adjust

Method used

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  • Indolocarbazole derivative and application thereof to electroluminescent device
  • Indolocarbazole derivative and application thereof to electroluminescent device
  • Indolocarbazole derivative and application thereof to electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: C 4 Synthesis of DP-ICZ

[0023]

[0024] (1) Synthesis of Compound 1: Add 2.34g of indole, 2.10g of benzaldehyde and 50ml of acetonitrile into a 100ml two-necked bottle, add 0.75ml of iodic acid aqueous solution (mass concentration 45%) into the bottle under nitrogen, and reflux for 14 Cool to 0°C, filter with suction, wash with acetonitrile at 0°C to obtain a white solid. Put this white solid into a 100ml two-necked bottle, add 60ml of acetonitrile, add 2.0g of iodine under nitrogen; reflux for 10 hours, then distill off the solvent under reduced pressure, add 150ml of sodium thiosulfate aqueous solution (concentration: 10g / 100ml) After stirring for 20 minutes, compound 1 was obtained by filtration, which was directly used in the next reaction.

[0025] (2)C 4 Synthesis of DP-ICZ: Add 408mg of compound 1 and 15ml of DMSO to a 100ml two-necked bottle, add 3ml of sodium hydroxide solution (concentration: 1g / 1ml) under a nitrogen atmosphere, then immedia...

Embodiment 2

[0025] (2)C 4 Synthesis of DP-ICZ: Add 408mg of compound 1 and 15ml of DMSO to a 100ml two-necked bottle, add 3ml of sodium hydroxide solution (concentration: 1g / 1ml) under a nitrogen atmosphere, then immediately add 736mg of iodo-n-butane, stir at room temperature for 20 After one hour, the reaction mixture was poured into 200ml of water, stirred for 20 minutes and then filtered to obtain the yellow-green solid product C 4 DP-ICZ (50% yield). Mass Spectrum m / z:520.50[M] + (calculated value: 520.29). Theoretical element content (%)C 56 h 66 N 4 O 2 : C87.65, H6.97, N5.38; measured element content (%) C87.80, H6.98, N5.44. The above analysis results show that the obtained product is the expected product. Example 2: C 4 Synthesis of DN-ICZ

[0026]

[0027] (1) Synthesis of Compound 2: Add 2.34g of indole, 3.12g of benzaldehyde and 50ml of acetonitrile into a 100ml two-necked bottle, add 0.75ml of iodic acid aqueous solution (concentration: 45%) into the bottle unde...

Embodiment 3

[0029] Example 3: C 1 Synthesis of DP-ICZ

[0030]

[0031] C 1 DP-ICZ

[0032] C 1 Synthesis of DP-ICZ with C 4 The DP-ICZ route is exactly the same, except that methyl iodide is used in the last step of alkylation. Mass Spectrum m / z:436.11[M] + (calculated value: 436.19). Theoretical element content (%)C 32 h 24 N 2 : C, 88.04; H, 5.54; N, 6.42; Measured element content (%) C, 88.10; H, 5.53; N, 6.40. The above analysis results show that the obtained product is the expected product.

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Abstract

The invention discloses an indolocarbazole derivative and an application thereof to an electroluminescent device, belonging to the technical field of organic electroluminescence. The indolocarbazole derivative has the structural formula shown as the specification, wherein R1 is H, CH3 or straight-chain or non-straight-chain alkyls with 4-10 atoms; R2 is H, F, Cl, Br or straight-chain or non-straight-chain alkyls with 1-4 carbon atoms; and R3 is H, F, Cl, Br or straight-chain or non-straight-chain alkyls with 1-4 carbon atoms. The indolocarbazole derivative can be used for preparing a luminous layer and a hole transportation layer of the electroluminescent device or used as a main doping body for preparing the luminous layer of the electroluminescent device. The device can be used in the application fields such as a lighting source, a signal lamp, an alphanumeric display, a signpost, a photoelectric coupler, a flat panel display and the like.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence, and specifically relates to a class of indolocarbazole derivatives and their application in electroluminescent devices. Background technique [0002] Pope et al first reported the phenomenon of organic electroluminescence in the early 1960s. They observed the blue light emitted by anthracene when a high voltage of 400 volts was applied to both sides of anthracene single crystal. However, due to the difficulty of growing single crystals and the high driving voltage of the device (400-2000V), the process they used has almost no 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-hydroxyquinoline as the light-emitting layer, and indium tin oxide (ITO) films and metal alloys were used as anode and cathode, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C09K11/06H01L51/54
Inventor 王悦
Owner JILIN YUANHE ELECTRONICS MATERIALS CO LTD