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

A technology of electroluminescent devices and organic compounds, applied in organic chemistry, electric solid devices, electrical components, etc., can solve problems such as performance differences

Inactive Publication Date: 2017-06-23
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

[0068] Embodiment 1: the synthesis of intermediate I

[0069]

[0070] (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 1, The molar ratio of 3,5-tribromobenzene to raw material U is 1:1.2~2.0; 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.

[0071] (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-...

Embodiment 2

[0082] Embodiment 2: the synthesis of compound 4:

[0083]

[0084] 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 point plate, the reaction was complete; natural cooling, filtration, filtrate rotary evaporation, silica gel column, to obtain the target product, HPLC purity 98.9%, yield 71.4%.

[0085] Elemental analysis structure (molecular formula C 50 h 35 NO): Theoretical C, 90.19; H, 5.30; N, 2.10; O, 2.40; Tested: C, 90.17; H, 5.31; N, 2.11;

[0086] ESI-MS(m / z)(M + ): The theoretical value is 665.27, and the measured value is 665.57.

Embodiment 3

[0087] Embodiment 3: the synthesis of compound 8:

[0088]

[0089] (1) In a 250ml three-necked flask, add 0.04mol raw material B1, 0.06mol 1,4-dibromobenzene, 0.12mol sodium tert-butoxide, 4×10 -4 mol Pd 2 (dba) 3 , 4×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampled on a plate, and the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain intermediate C1 with a HPLC purity of 99.3% and a yield of 62.4%.

[0090] Elemental analysis structure (molecular formula C 20 h 16 BrN): Theoretical C, 68.58; H, 4.60; Br, 22.81; N, 4.00; Found: C, 68.55; H, 4.63; Br, 22.80; N, 4.02. ESI-MS(m / z)(M + ): The theoretical value is 349.05, and the measured value is 349.37.

[0091](2) In a 250ml three-necked flask, under a nitrogen atmosphere, add 0.02mol of intermediate C1, 40ml of tetrahydrofuran to dissolve completely, cool to -78°C, and then add 15mL of 1...

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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. [0003] 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 t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/10C07D409/14C07D487/04C07D405/14C07D409/10C07D405/10C07D307/91C09K11/06H01L51/54
CPCC09K11/06C07D307/91C07D403/10C07D405/10C07D405/14C07D409/10C07D409/14C07D487/04C09K2211/1029C09K2211/1044C09K2211/1088C09K2211/1092H10K85/622
Inventor 李萍唐丹丹李崇张兆超张小庆
Owner VALIANT CO LTD
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