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A kind of organic compound containing dibenzo six-membered ring and its application

An organic compound and six-membered ring technology, which is applied to compound materials containing a dibenzo six-membered ring structure as the central skeleton, and the application field in the field of OLEDs, which can solve very different problems

Active Publication Date: 2020-04-14
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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  • A kind of organic compound containing dibenzo six-membered ring and its application
  • A kind of organic compound containing dibenzo six-membered ring and its application
  • A kind of organic compound containing dibenzo six-membered ring and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Embodiment 1: the synthesis of intermediate BI:

[0056]

[0057] (1) In a 250ml three-necked flask, under a nitrogen atmosphere, add 0.1mol raw material M, 0.15mol raw material N, 0.3mol sodium tert-butoxide, 1×10 -3 mol Pd 2 (dba) 3 , 1×10 -3 mol P(t-Bu) 3 , 150ml of toluene, heated and refluxed for 24 hours, sampled and plated, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain intermediate L with a HPLC purity of 99.2% and a yield of 50.4%.

[0058] (2) In a 250ml three-necked flask, under a nitrogen atmosphere, add 0.05mol intermediate L, 0.15mol sodium tert-butoxide, 5×10 -4 mol Pd 2 (dba) 3 , 5×10 -4 mol ArNPCy 2 (2-dicyclohexylphosphino-2'-(N,N-dimethylamine)-biphenyl), 150ml 1,4-dioxane, heated to 110°C for 15 hours, sampled and plated, the reaction was complete; Naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel colu...

Embodiment 2

[0060] Embodiment 2: the synthesis of intermediate BII:

[0061]

[0062] (1) In a 250ml three-necked flask, under a nitrogen atmosphere, add 0.1mol raw material M, 0.15mol raw material N, 0.3mol sodium tert-butoxide, 1×10 -3 mol Pd 2 (dba) 3 , 1×10 -3 mol P(t-Bu) 3 , 150ml of toluene, heated and refluxed for 24 hours, sampled and plated, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain intermediate L with a HPLC purity of 99.2% and a yield of 50.4%.

[0063] (2) In a 250ml three-necked flask, under a nitrogen atmosphere, add 0.05mol intermediate L, 0.15mol sodium tert-butoxide, 5×10 -4 mol Pd 2 (dba) 3 , 5×10 -4 mol ArNPCy 2 (2-dicyclohexylphosphino-2'-(N,N-dimethylamine)-biphenyl), 150ml 1,4-dioxane, heated to 110°C for 15 hours, sampled and plated, the reaction was complete; Naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel col...

Embodiment 3

[0064] Embodiment 3: the synthesis of intermediate BIII:

[0065]

[0066] (1) In a 250ml three-neck flask, under a nitrogen atmosphere, add 0.1mol raw material O, 0.15mol raw material N, 0.3mol sodium tert-butoxide, 1×10 -3 mol Pd 2 (dba) 3 , 1×10 -3 mol P(t-Bu) 3 , 150ml of toluene, heated and refluxed for 24 hours, sampled and plated, the reaction was complete; natural cooling, filtration, filtrate rotary evaporation, silica gel column, to obtain intermediate P, HPLC purity 99.1%, yield 56.4%.

[0067] (2) In a 250ml three-necked flask, under a nitrogen atmosphere, add 0.05mol of intermediate P, 0.15mol of sodium tert-butoxide, 5×10 -4 mol Pd 2 (dba) 3 , 5×10 -4 mol ArNPCy 2 (2-dicyclohexylphosphino-2'-(N,N-dimethylamine)-biphenyl), 150ml 1,4-dioxane, heated to 110°C for 15 hours, sampled and plated, the reaction was complete; Naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain intermediate BIII with a...

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Abstract

The invention discloses an organic compound and an application thereof to an OLED (organic light emission diode) device. The organic compound contains dibenzo six-membered rings, and oxygen atoms, sulfur atoms, C1-10 linear or branched alkyl substituted alkylidene, aryl substituted alkylidene and alkyl or aryl substituted tertiary amide are contained between the two dibenzo six-membered rings. Thecompound has higher glass transition temperature and molecular thermal stability and appropriate HOMO and LUMO energy level, and photoelectric property of the OLED device can be effectively improvedand the service life of the OLED device can be effectively prolonged through structural optimization of the device.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound material containing a dibenzo six-membered ring structure as a central skeleton and its application in the field of OLEDs. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. The OLED light-emitting device is like a sandwich structure, including electrode material film layers, and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both ends of the OLED ligh...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/14C07D405/10C07D491/048C07D471/04C07D491/052C07D491/153C07D498/04C07D487/04C07D491/056C07D487/14C07D491/044C07D491/147C07D223/14C07D495/04C07D495/14C07D403/14C09K11/06H01L51/54H01L51/50
Inventor 吴秀芹杨福山张兆超李崇
Owner JIANGSU SUNERA TECH CO LTD
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