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Compound with carbazole as core, and application thereof in organic light-emitting devices

A compound and compound structure technology, applied in the application field of organic electroluminescent devices, can solve the problems of different performance, achieve the effect of stable three-dimensional structure, improve hole injection and transport performance, improve current efficiency and lifespan

Inactive Publication Date: 2019-12-17
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 with carbazole as core, and application thereof in organic light-emitting devices
  • Compound with carbazole as core, and application thereof in organic light-emitting devices
  • Compound with carbazole as core, and application thereof in organic light-emitting devices

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0053] Preparation of Intermediate I1

[0054]

[0055] In a 250mL three-neck flask, under a nitrogen atmosphere, add 0.01mol raw material A1, 0.012mol raw material B1, 0.03mol potassium carbonate, 1×10 -4 molCuI, 1×10 -4 mol 1,10-phenanthroline, 150ml DMF, heated to reflux for 15h, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain intermediate I1; HPLC purity 97.9%, yield 74.6%;

[0056] Elemental analysis structure (molecular formula C 30 h 21 BrN 2 ): theoretical value C, 73.62; H, 4.33; Br, 16.33; N, 5.72; tested value: C, 73.60; H, 4.34; Br, 16.33; N, 5.73. ESI-MS (m / z) (M+): The theoretical value is 488.09, and the measured value is 488.27.

[0057] The preparation method of other intermediate I is similar to the preparation method of intermediate I1, and the specific structure of intermediate I used in the present invention is shown in Table 1.

[0058] Table 1

[0059] ...

Embodiment 1

[0077] The preparation of embodiment 1 compound 1

[0078]

[0079] In a 250mL three-necked flask, nitrogen was introduced, 0.01mol intermediate I1 and 0.015mol intermediate II1 were added, dissolved in a mixed solvent of toluene and ethanol (90mL of toluene, 45mL of ethanol), and then 0.03mol of Na 2 CO 3 Aqueous solution (2M), stirred with nitrogen for 1h, then added 0.0001mol Pd(PPh 3 ) 4, Heated to reflux for 15h, sampled and plated, the reaction was complete. After natural cooling, filtration, rotary evaporation of the filtrate, and passing the residue through a silica gel column, the target product was obtained with a purity of 98.1% and a yield of 76.2%. Elemental analysis structure (molecular formula C 57 h 41 N 3 ): theoretical value C, 89.15; H, 5.38; N, 5.47; test value: C, 89.16; H, 5.37; N, 5.47. ESI-MS (m / z) (M+): theoretical value 767.33, found value 767.51.

Embodiment 2

[0080] The preparation of embodiment 2 compound 9

[0081]

[0082] The preparation method of compound 9 is the same as that of Example 1, except that intermediate II2 is used to replace intermediate II1. Elemental analysis structure (molecular formula C 57 h 41 N 3 ): theoretical value C, 89.15; H, 5.38; N, 5.47; test value C, 89.16; H, 5.38; N, 5.46. ESI-MS (m / z) (M+): theoretical value 767.33, found value 767.28.

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Abstract

The invention relates to a compound with carbazole as a core, and a preparation method and an application thereof. The structure of the compound is characterized in that carbazole is connected with atriphenylamine structure through a carbon-nitrogen bond, and the carbon-nitrogen bond connection avoids exposure of an active position; carbazole is connected with a dibenzo five-membered ring througha carbon-carbon bond, so the chemical stability of the above material is improved; the whole molecule is of a large rigid structure, and has a high triplet state energy level (T1); the compound has alarge steric hindrance, and is not prone to rotate, and the three-dimensional space structure is stable, so the compound has a high glass transition temperature and a high molecular thermal stability; and HOMO and LUMO distribution positions of the compound are separated from each other, so the compound has appropriate HOMO and LUMO energy levels, thereby the compound can effectively improve theluminous efficiency and the service life of OLEDs when applied to the OLEDs.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an organic compound with a carbazole structure as the core and a triarylamine structure and its application in an organic electroluminescent device. Background technique [0002] Organic Light Emission Diodes (OLED) device technology can be used not only to manufacture new display products, but also to make new lighting products. It 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. OLED light-emitting devices are current devices. When a voltage is applied to the electrodes at both ends, and th...

Claims

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Application Information

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IPC IPC(8): C07D209/94C07D491/048C07D495/04C07D487/04C07D498/04C07D401/04C07D405/04C07D209/80C07D409/04C07D209/86C07D413/04C07D519/00C07D471/04C07D405/14C07D405/12C09K11/06H01L51/50H01L51/54
CPCC07D209/94C07D491/048C07D495/04C07D487/04C07D498/04C07D401/04C07D405/04C07D209/80C07D409/04C07D209/86C07D413/04C07D519/00C07D471/04C07D405/14C07D405/12C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1033C09K2211/1088C09K2211/1092H10K85/624H10K85/636H10K85/633H10K85/655H10K85/615H10K85/631H10K85/654H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/11
Inventor 李崇庞羽佳张兆超赵四杰
Owner JIANGSU SUNERA TECH CO LTD
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