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Organic compounds using homobenzenes as core and application thereof in organic electroluminescent devices

An organic compound and organic technology, applied to the application of organic electroluminescent devices, in the field of organic compounds, can solve problems such as performance differences, achieve high film stability, improve current efficiency and life, and reduce efficiency roll-off effects

Inactive Publication Date: 2017-05-17
VALIANT 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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  • Organic compounds using homobenzenes as core and application thereof in organic electroluminescent devices
  • Organic compounds using homobenzenes as core and application thereof in organic electroluminescent devices
  • Organic compounds using homobenzenes as core and application thereof in organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1: the synthesis of intermediate I

[0052]

[0053] (1) Weigh 1,3,5-tribromobenzene and raw material U(Ar 1 -B(OH) 2 ), dissolved in a mixed solvent of toluene and ethanol with a volume ratio of 1.5 to 3.0:1; then add Na 2 CO 3 Aqueous solution, Pd(PPh 3 ) 4 ; Under an inert atmosphere, stir the above mixed solution at 95-100°C for 10-24 hours, then cool to room temperature, filter the reaction solution, spin the filtrate, and pass through a silica gel column to obtain intermediate V; the raw material U The molar ratio to 1,3,5-tribromobenzene is 1:1.5~3.0; Pd(PPh 3 ) 4 The molar ratio to raw material U is 0.006~0.02:1, Na 2 CO 3 The molar ratio to raw material U is 2.0-3.0:1.

[0054] (2) Weigh intermediate V and raw material W, and dissolve them in a mixed solvent of toluene and ethanol with a volume ratio of 1.5 to 3.0:1; then add Na 2 CO 3 Aqueous solution, Pd(PPh 3 ) 4 ; Under an inert atmosphere, stir the above mixed solution at 95-100°...

Embodiment 2

[0065] Embodiment 2: the synthesis of compound 5:

[0066]

[0067] In a 250ml three-necked flask, under a nitrogen atmosphere, add 0.01mol of intermediate A1, 0.015mol of raw material B1, 0.03mol of sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampling plate, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 98.8% and a yield of 72.3%.

[0068] Elemental analysis structure (molecular formula C 48 h 29 NO 2 ): theoretical value C, 88.46; H, 4.48; N, 2.15; O, 4.91; test value: C, 88.45; HPLC-MS: The theoretical molecular weight of the material is 651.22, and the measured molecular weight is 651.53.

Embodiment 3

[0069] Embodiment 3: the synthesis of compound 10:

[0070]

[0071] In a 250ml three-necked flask, add 0.01mol intermediate A2, 0.015mol raw material B1, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampling point plate, the reaction was complete; naturally cooled, filtered, filtrate was rotary evaporated, passed through a silica gel column to obtain the target product with a purity of 98.9% and a yield of 71.8%.

[0072] Elemental analysis structure (molecular formula C 48 h 27 NO 3 ): theoretical value C, 86.60; H, 4.09; N, 2.10; O, 7.21; test value: C, 86.61; H, 4.07; N, 2.12; HPLC-MS: The theoretical molecular weight of the material is 665.20, and the measured molecular weight is 665.48.

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Abstract

The invention relates to organic compounds using homobenzenes as a core and application thereof in OLED (organic light-emitting diode) devices. The compounds have higher glass transition temperature, higher molecular heat stability, appropriate HOMO and LUMO energy levels and higher Eg. The device structure is optimized, thereby effectively enhancing the photoelectric properties of the OLED devices and prolonging the service life of the OLED devices.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an organic compound with homobenzene as the core and its application in organic electroluminescent devices. 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. OLED light-emitting devices are current devices. When a voltage is applied to the electrodes at both ends, and the positi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/10C07D409/14C07D421/10C07D405/04C07D491/048C07D405/14C07D209/94C07D487/04C07D409/10C07D495/04C07D491/153C07D487/14C07D495/14C07D491/052C07D498/04C07D513/04C07D491/056C07D517/04C07D498/14C07D491/044H01L51/54
CPCC07D209/94C07D405/04C07D405/10C07D405/14C07D409/10C07D409/14C07D421/10C07D487/04C07D487/14C07D491/044C07D491/048C07D491/052C07D491/056C07D491/153C07D495/04C07D495/14C07D498/04C07D498/14C07D513/04C07D517/04H10K85/615H10K85/626H10K85/653H10K85/655H10K85/657H10K85/6572H10K85/6574H10K85/6576
Inventor 唐丹丹李崇张兆超张小庆徐凯
Owner VALIANT CO LTD
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