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Triphenylene-based fused biscarbazole derivative and use thereof

A technology of biscarbazoles and triphenylenes, applied in the field of compounds, can solve the problems of lack of materials, half-life, efficiency and unsatisfactory driving voltage, etc.

Inactive Publication Date: 2017-01-04
LUMINESCENCE TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Taking the full-colored flat panel display of AMOLED or OLED lighting panel (full-colored flat panel display), currently the relevant materials for the phosphorescent host in the light-emitting layer are still in the half-life, efficiency and driving voltage in industrial applications. Not ideal, such materials are still missing

Method used

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  • Triphenylene-based fused biscarbazole derivative and use thereof
  • Triphenylene-based fused biscarbazole derivative and use thereof
  • Triphenylene-based fused biscarbazole derivative and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] Embodiment 1: the synthesis of compound EX10

[0082] Synthesis of 2-(biphenyl-2-yl)-7-bromo-9,9-dimethyl-9H-fluorene (2-(biphenyl-2-yl)-7-bromo-9,9-dimethyl-9H- fluorene)

[0083]

[0084] 35.2g (100mmol) 2,7-dibromo-9,9-dimethyl-9H-fluorene (2,7-dibromo-9,9-dimethyl-9H-fluorene), 21.8g (110mmol) biphenyl- 2-base boronic acid (biphenyl-2-ylboronic acid), 2.31g (2mmol) four (triphenylphosphine) palladium (tetrakis (triphenylphosphine) palladium, Pd (PPh 3 ) 4 ), 75ml 2M sodium carbonate (Na 2 CO 3 ), 150 ml of ethanol (EtOH) and 300 ml of toluene (toluene) were degassed and placed under nitrogen, followed by heating at 100° C. for 12 hours to react. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate and water, and the extracted organic layer was dried with anhydrous magnesium sulfate to remove the solvent to form a residue, which was passed through a tube filled with silica gel. T...

Embodiment 2

[0115] Embodiment 2: the synthesis of compound EX16

[0116] Synthesis of 2-(10,10-dimethyl-10H-indeno[2,1-b]triphenylene-12-yl)-4,4,5,5-tetramethyl-1,3,2-di Oxaborolane (2-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane )

[0117]

[0118] 10.7g (25.3mmol) 12-bromo-10,10-dimethyl-10H-indeno[1,2-b]triphenylene, 7.7g (30.3mmol) bis(pinacolate) diboron, 0.3 A mixture of g (0.26mmol) tetrakis(triphenylphosphine) palladium, 7.4g (75.4mmol) potassium acetate (potassium acetate) and 300ml 1,4-dioxane was degassed and placed under nitrogen, then heated at 90 °C for 16 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic phase was separated and washed with ethyl acetate and water, and then dried with anhydrous magnesium sulfate, and the solvent was removed under vacuum to form a residue. The residue was purified by column chromatography packed with silica gel (hexane-dichloromethane) to ...

Embodiment 3

[0146] Embodiment 3: the synthesis of compound EX27

[0147] Synthesis of intermediate IX (intermediate IX)

[0148]

[0149] 5.5g (11.8mmol) 10,10-dimethyl-12-(2-nitrophenyl)-10H-indeno[2,1-b]triphenylene, 30ml triethyl phosphite, 15ml 1, The mixture of 2-dichlorobenzene was placed under a nitrogen atmosphere, followed by heating at 160° C. overnight for the reaction. After the reaction was completed, the mixture was cooled to room temperature, and 200 ml of methanol was added to the cooled mixture and stirred, and after suction filtration, a precipitate was formed. Using a mixture of hexane and dichloromethane as the eluent, the precipitate was purified by column chromatography packed with silica gel to obtain 2.1 g of a yellow product with a yield of 41%.

[0150] Synthetic intermediate X (intermediate X)

[0151]

[0152]1.9g (4.4mmol) intermediate IX, 1.2g (5.8mmol) iodobenzene, 0.85g (8.8mmol) sodium tert-butoxide and 0.5ml (0.5mmol) tri-tert-butylphosphine were...

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Abstract

The present invention discloses a triphenylene-based fused biscarbazole derivative expressed by a formula (1) or formula (2) and the use thereof. The triphenylene-based fused biscarbazole derivative can be used in an organic EL component mainly as a light emitting host of a light emitting layer, so that the organic EL component having low drive voltage, low power consumption, high efficiency and long half-life time. The invention also relates to an organic EL component containing the derivative expressed by the formula (1) or formula (2).

Description

technical field [0001] The present invention relates to a compound, which is a triphenylene-based biscarbazole condensed derivative and the application of the compound. Specifically, the present invention relates to a compound having a structure shown in formula (1) or formula (2), and an organic electro-optic material using a compound having a structure of formula (1) or formula (2) in a light-emitting layer. Excitation light components and related devices, flat panels, etc. Background technique [0002] Organic electroluminescence (organic EL) is a light-emitting diode (LED) in which the light-emitting layer is a film made of an organic compound that emits light under a corresponding electric current. A light-emitting layer of organic compounds is sandwiched between the two electrodes. Organic EL is used in flat panel displays due to its high illumination, low weight, ultra-thin profile, self-illumination without backlight, low power consumption, wide viewing angle, high...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07D471/14C09K11/06H01L51/54H10K99/00
CPCC07D471/04C07D471/14C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1059C09K2211/1044C09K2211/1033C09K2211/1037C09K2211/1088C09K2211/1092H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K50/11C07D403/10C07D251/24C09K11/02C09K2211/185H10K85/654H10K85/342H10K2101/10H10K2101/90
Inventor 颜丰文
Owner LUMINESCENCE TECH
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