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Organic compound containing spiro-fluorene anthrone structure and application thereof

A technology of an organic compound, spirofluoranthrone, applied in the application field of organic electroluminescent devices, which can solve different problems

Active Publication Date: 2020-01-03
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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  • Organic compound containing spiro-fluorene anthrone structure and application thereof
  • Organic compound containing spiro-fluorene anthrone structure and application thereof
  • Organic compound containing spiro-fluorene anthrone structure and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0116] The preparation of embodiment 1 intermediate

[0117] (1) Preparation of Intermediate A1

[0118]

[0119] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material O1, 0.012mol raw material P1, 150ml toluene and stir to mix, then add 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol P(Ph) 3 , 0.03mol sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated to no fraction, passed through a neutral silica gel column , obtain target product intermediate A1; HPLC purity 99.67%, yield 77.8%; Elemental analysis structure (molecular formula C 24 h 19 N): Theoretical value: C, 89.68; H, 5.96; N, 4.36; Tested value: C, 89.67; H, 5.96; N, 4.37. ESI-MS(m / z)(M + ): The theoretical value is 321.42, and the measured value is 321.45.

[0120] (2) Preparation of Intermediate B1

[0121]

[0122...

Embodiment 2

[0131] The preparation of embodiment 2 compound 7

[0132]

[0133] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material 1, 0.012mol intermediate A1, 150ml toluene and stir to mix, then add 5×10 -5 molPd 2 (dba) 3 , 5×10 -5mol P(t-Bu) 3 , 0.03mol sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated to no fraction, passed through a neutral silica gel column , the target product was obtained, the HPLC purity was 99.88%, and the yield was 77.3%. Elemental analysis structure (molecular formula C 50 h 33 NO): Theoretical: C, 90.47; H, 5.01; N, 2.11; 0, 2.41; Tested C, 90.46; HPLC-MS: The molecular weight of the material is 663.82, and the measured molecular weight is 663.85.

Embodiment 3

[0134] The preparation of embodiment 3 compound 26

[0135]

[0136] The preparation method of compound 26 is the same as that in Example 2, except that raw material 1 is replaced by raw material 2, and intermediate A1 is replaced by intermediate A2. Elemental analysis structure (molecular formula C 53 h 37 NO): Theoretical: C, 90.44; H, 5.30; N, 1.99; 0, 2.27; Tested: C, 90.43; H, 5.30; N, 1.99; ESI-MS(m / z)(M + ): The theoretical value is 703.88, and the measured value is 703.90.

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Abstract

The invention discloses an organic compound containing a spiro-fluorene anthrone structure and an application thereof. The pi-conjugation effect in the compound makes the compound have a strong hole-transporting ability, and a high hole-transporting rate can reduce a start voltage of a device, and improves the efficiency of an organic light emission device. The asymmetric triarylamine structure can reduce crystallinity and planarity of the molecule, and prevents the molecule from moving on the plane, and thereby thermal stability of the molecule is improved. At the same time, the structure ofthe provided compound makes distribution of electrons and holes in a light-emitting layer more balanced, the hole injection and transport performance is improved under an appropriate HOMO energy level, and a role of electron blocking is played under an appropriate LUMO energy level, and the recombination efficiency of exciton in light-emitting layer is improved.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an organic compound containing spirofluoranthrone in its structure 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. As a current device, when a voltage is applied to the electrodes at both ends of the OLED light-emitti...

Claims

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Application Information

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IPC IPC(8): C07C225/22C07C255/58C07D307/77C07D307/91C07D209/88C07D311/78H01L51/50H01L51/54
CPCC07C225/22C07C255/58C07D307/77C07D307/91C07D209/88C07D311/78C07C2603/18C07C2603/54H10K85/615H10K85/636H10K85/626H10K85/633H10K85/6574H10K85/6572H10K50/00Y02E10/549
Inventor 李崇吴秀芹张兆超王芳庞羽佳
Owner JIANGSU SUNERA TECH CO LTD
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