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Compound containing spirofluorene structure, and applications in organic electroluminescent devices

A technology of spirofluorene structure and compound, which can be used in electric solid devices, electrical components, luminescent materials, etc., and can solve problems such as different

Inactive Publication Date: 2019-06-21
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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  • Compound containing spirofluorene structure, and applications in organic electroluminescent devices
  • Compound containing spirofluorene structure, and applications in organic electroluminescent devices
  • Compound containing spirofluorene structure, and applications in organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0102] Embodiment 1: the synthesis of compound 2:

[0103]

[0104] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material A1, 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 and pointing plate, showed that no raw material A1 remained, and the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was subjected to vacuum rotary evaporation (-0.09MPa, 85°C ), through a neutral silica gel column to obtain the target product, with a HPLC purity of 99.3% and a yield of 84.7%;

[0105] Elemental analysis structure (molecular formula C 49 h 29 NO 2 ): theoretical value C, 88.67; H, 4.40; N, 2.11; O, 4.82; test value: C, 88.75; H, 4.45; N, 2.15; ESI-MS(m / z)(M + ): The theoretical value is 663.22, and the measured value is 663.29.

Embodiment 2

[0106] Embodiment 2: the synthesis of compound 7:

[0107]

[0108] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material A1, 0.012mol intermediate 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 and pointing plate, showed that no raw material A1 remained, and the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was subjected to vacuum rotary evaporation (-0.09MPa, 85°C ), through a neutral silica gel column to obtain the target product, with a HPLC purity of 99.5% and a yield of 82.9%;

[0109] Elemental analysis structure (molecular formula C 52 h 35 NO): theoretical value C, 90.54; H, 5.11; N, 2.03; 0, 2.32; found value: C, 90.58; H, 5.13; N, 2.06; ESI-MS(m / z)(M + ): The theoretical value is 689.27, and the measured value is 689.32.

Embodiment 3

[0110] Embodiment 3: the synthesis of compound 16:

[0111]

[0112] The preparation method of compound 16 is the same as that of Example 1, except that intermediate B3 is replaced by intermediate B1. Elemental analysis structure (molecular formula C 52 h 35 NO): Theoretical C, 90.54; H, 5.11; N, 2.03; O, 2.32; Tested: C, 90.57; H, 5.16; N, 2.09; ESI-MS(m / z)(M + ): The theoretical value is 689.27, and the measured value is 689.36.

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Abstract

The invention discloses a compound containing a spirofluorene structure, and applications in organic electroluminescent devices. According to the present invention, the compound has strong rigidity due the spirofluorene structure; the compound has characteristics of less intermolecular crystallization, less aggregation, good film forming property and the like after the compound is linked to a carbazole derivative long branch chain structure; the mother nucleus of the compound has bipolarity, the branch chain is the electron donating group, and the electron donating abilities of the branch chain groups are different, such that the material has different HOMO energy levels so as to be used as different function layer materials; the compound has high triplet energy level so as to effectivelyblock energy loss and easily achieve energy transfer; and with the application of the compound as the organic electroluminescent function layer material in OLED devices, the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved, and the service life of the device is significantly prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound containing a spirofluorene structure and its application in an organic electroluminescence 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 electrodes at both ends of the OLED light-emitting de...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/04C07D491/048C07D487/04C07D495/04C07D491/052C07D471/04C07D498/04C07D405/10C07D405/14C07D519/00C07D491/107C07D209/56C07D209/88C09K11/06H01L51/50H01L51/54
Inventor 王芳张兆超李崇张小庆
Owner JIANGSU SUNERA TECH CO LTD
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