Compound containing spiro-xanthene fluorene and application of compound to organic light-emitting device

A technology of compound and xanthene, applied in organic light-emitting devices, materials of organic semiconductor devices, electric solid-state devices, 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

Method used

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  • Compound containing spiro-xanthene fluorene and application of compound to organic light-emitting device
  • Compound containing spiro-xanthene fluorene and application of compound to organic light-emitting device
  • Compound containing spiro-xanthene fluorene and application of compound to organic light-emitting device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0114] Embodiment 1: the synthesis of compound 8:

[0115]

[0116] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material A1, 0.012mol raw material B1, 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 a neutral silica gel column, to obtain the target product, HPLC purity 99.3%, yield 84.7%;

[0117] Elemental analysis structure (molecular formula C 49 h 30 N 2 O): theoretical value C, 88.80; H, 4.56; N, 4.23; O, 2.41; tested value: C, 88.75; H, 4.65; N, 4.05; ESI-MS(m / z)(M + ): The theoretical value is 662.24, and the measured value is 662.79.

Embodiment 2

[0118] Embodiment 2: the synthesis of compound 15:

[0119]

[0120] In a 250ml three-necked flask, under the protection of nitrogen, add 0.01mol raw material A1, 0.012mol raw material B2, 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 a neutral silica gel column, to obtain the target product, HPLC purity 99.5%, yield 82.9%;

[0121] Elemental analysis structure (molecular formula C 46 h 31 NO): theoretical value C, 90.02; H, 5.09; N, 2.28; 0, 2.61; tested value: C, 90.08; ESI-MS(m / z)(M + ): The theoretical value is 613.24, and the measured value is 613.76.

Embodiment 3

[0122] Embodiment 3: the synthesis of compound 16:

[0123]

[0124] The preparation method of compound 16 is the same as that in Example 1, except that raw material B1 is replaced with raw material B3.

[0125] Elemental analysis structure (molecular formula C 49 h 30 N 2 O): theoretical value C, 88.80; H, 4.56; N, 4.23; O, 2.41; tested value: C, 88.77; H, 4.49; N, 4.09; ESI-MS(m / z)(M + ): The theoretical value is 662.24, and the measured value is 662.59.

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Abstract

The invention discloses a compound containing spiro-xanthene fluorene and an application of the compound to an organic light-emitting device. The compound has a spiro-xanthene fluorene structure, so that the compound has high rigidity and the advantages that crystallization and aggregation between molecule cannot be easily formed, and the compound has good film-forming property and the like afterbeing connected with a long-chain branch structure of a carbazole derivative. A parent nucleus of the compound has double polarity, a branch chain is provided with an electron-donating group, the electron donating abilities of a branch chain group are different, so that HOMO energy levels of a material are different, and the compound can serve as different functional layer materials to be used. The compound has higher triplet-state energy levels, energy loss can be effectively blocked, and energy transfer is facilitated. The compound serves as an organic light-emitting functional layer material to be applied to an OLED (organic light-emitting diode) device, current efficiency, power efficiency and external quantum efficiency of the device are greatly improved, and the service life of the device is obviously prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound containing oxaspirofluorene and a nitrogen-containing five-membered heterocyclic ring, and its application in an organic electroluminescent device. Background technique [0002] Organic electroluminescence (OLED: Organic Light Emission Diodes) device technology can not only be used to manufacture new display products, but also can be used to make new lighting products, and is expected to replace the existing liquid crystal display and fluorescent lighting, and has a very wide application prospect . The OLED light-emitting device is 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 elec...

Claims

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Application Information

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IPC IPC(8): C07D491/048C07D495/04C07D405/04C07D487/04C07D491/056C07D491/052C07D498/04C07D471/04C07D513/04C07D405/10C07D498/14C07D405/14C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D405/04C07D405/10C07D405/14C07D471/04C07D487/04C07D491/048C07D491/052C07D491/056C07D495/04C07D498/04C07D498/14C07D513/04C09K2211/1033C09K2211/1037C09K2211/1029C09K2211/1007C09K2211/1088H10K85/6574H10K85/657H10K50/11H10K2101/40H10K85/6572H10K50/18H10K50/15H10K2102/00H10K2102/301
Inventor 王立春王芳张兆超李崇张小庆
Owner JIANGSU SUNERA TECH CO LTD
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