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Dibenzo-hexatomic ring-cored compound and application thereof to organic electroluminescent device

A compound and six-membered ring technology, which can be used in electric solid devices, electrical components, luminescent materials, etc., can solve very different problems

Inactive Publication Date: 2019-04-05
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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  • Dibenzo-hexatomic ring-cored compound and application thereof to organic electroluminescent device
  • Dibenzo-hexatomic ring-cored compound and application thereof to organic electroluminescent device
  • Dibenzo-hexatomic ring-cored compound and application thereof to organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] Embodiment 1: the synthesis of intermediate BI and intermediate BII:

[0091]

[0092] 1) dissolving raw material O and raw material P with toluene, wherein, the molar ratio of raw material O and raw material P is 1:(1.0~1.5);

[0093] 2) Add Pd to the reaction system in 1) 2(dba) 3 , tri-tert-butylphosphine, sodium tert-butoxide; the Pd 2 (dba) 3 The molar ratio with raw material O is (0.005~0.01):1, the molar ratio of described tri-tert-butylphosphine and raw material O is (0.005~0.02):1, and the molar ratio of described sodium tert-butoxide and raw material O is (1.5~3.0):1;

[0094] 3) Under the protection of an inert gas, react the above-mentioned mixed solution at a temperature of 95-110° C. for 10-24 hours, naturally cool to room temperature, and filter the reaction solution. The filtrate is rotary evaporated to no solvent, and passed through a neutral silica gel column. Obtain intermediate B1;

[0095] Take the synthesis of intermediate B1 as an example...

Embodiment 2

[0112] Embodiment 2: the synthesis of compound 3:

[0113]

[0114] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material 1, 0.012mol intermediate B2, 150ml toluene and stir to mix, then add 0.02mol sodium carbonate, 1×10 -4 molPd(PPh 3 ) 4 , heated to 105 ° C, reflux reaction for 24 hours, sampling point plate, showing no bromide remaining, the reaction is complete; naturally cooled to room temperature, filtered, the filtrate was subjected to vacuum rotary evaporation (-0.09MPa, 85 ° C), passed through neutral silica gel Column, obtain target product, HPLC purity 99.0%, yield 75.3%; Elemental analysis structure (molecular formula C 54 h 34 N 2 o 3 ): Theoretical value: C, 85.47; H, 4.52; N, 3.69; O, 6.32; Test value: C, 85.43; H, 4.55; N, 3.65; ESI-MS(m / z)(M + ): The theoretical value is 758.88, and the measured value is 758.75.

Embodiment 3

[0115] Embodiment 3: the synthesis of compound 8:

[0116]

[0117] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material 2, 0.012mol intermediate B3, 150ml toluene and stir to mix, then add 0.03mol sodium tert-butoxide, 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylphosphine, heated to 105°C, refluxed for 24 hours, sampling plate, showed no remaining bromide, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated under reduced pressure (-0.09MPa, 85°C ), through neutral silica gel column, obtain target product, HPLC purity 98.5%, yield 67.8%; Elemental analysis structure (molecular formula C 54 h 44 N 2 ): Theoretical value: C, 89.96; H, 6.15; N, 3.89; Tested value: C, 89.94; H, 6.15; N, 3.91. ESI-MS(m / z)(M + ): The theoretical value is 720.96, and the measured value is 720.85.

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Abstract

The invention discloses a dibenzo-hexatomic ring-cored compound and application thereof to an organic electroluminescent device. The dibenzo-hexatomic ring-cored compound is in a structure shown as the formula (1). The prepared dibenzo-hexatomic ring-cored compound is high in glass transition temperature and molecular thermal stability and has appropriate T1 energy level, HOMO-LUMO (highest occupied molecular orbital-lowest unoccupied molecular orbital) energy level, and through device structural optimization, can effective increase the photoelectric property and the service life of OLED (organic light emitting diode) devices.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound material with a dibenzo-6-membered ring as the 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 new lighting products, and 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 light-emitting device, and the positive and neg...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D219/02C07D265/38C07D413/14C07D401/14C07D219/08C07D405/12C07D401/12C07D409/12C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D219/02C07D219/08C07D265/38C07D401/12C07D401/14C07D405/12C07D409/12C07D413/14C09K2211/1088C09K2211/1092C09K2211/1044C09K2211/1029C09K2211/1007C09K2211/1011C09K2211/1033H10K85/624H10K85/626H10K85/615H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/15H10K50/17
Inventor 吴秀芹张兆超李崇张小庆
Owner JIANGSU SUNERA TECH CO LTD
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