Organic compound taking carbazole derivative as core and application of same to organic light-emitting device

A technology of organic compounds and carbazoles, applied in organic chemistry, electrical solid-state devices, luminescent materials, etc., can solve problems such as performance differences

Active Publication Date: 2020-07-07
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 taking carbazole derivative as core and application of same to organic light-emitting device
  • Organic compound taking carbazole derivative as core and application of same to organic light-emitting device
  • Organic compound taking carbazole derivative as core and application of same to organic light-emitting device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1: the synthesis of intermediate A

[0052] Synthesis of Intermediate A-1

[0053]

[0054] (1) In a 250mL three-neck flask, under the protection of nitrogen, add 0.01mol raw material D-1, 0.015mol raw material E-1, dissolve with a mixed solvent of toluene and ethanol (90mL of toluene, 45mL of ethanol), and then add 0.03mol 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. Cool naturally, filter, spin evaporate the filtrate, and pass the residue through a silica gel column to obtain intermediate C-1; HPLC purity 97.7%, yield 85.9%;

[0055] Elemental analysis structure (molecular formula C 24 h 13 NO 4 ): theoretical value C, 75.98; H, 3.45; N, 3.69; 0, 16.87; test value: C, 75.96; ESI-MS (m / z) (M+): theoretical value 379.08, found value 379.05.

[0056] (2) In a 250mL three-neck flask, under the protection of nitrogen, add 0....

Embodiment 2

[0064] Embodiment 2: the synthesis of intermediate B

[0065] Synthesis of Intermediate B-11

[0066]

[0067] (1) In a 250mL three-necked flask, nitrogen gas was introduced, and 10.0mol raw material F-2, 12.0mol raw material G-1, 0.3g Pd(dppf)Cl 2 , 30.0mmol of potassium acetate was added to 100mL of 1,4-dioxane, and reacted for 5 hours at 130°C. The intermediate H-2 was obtained by separation and purification through silica gel column chromatography, the HPLC purity was 99.8%, and the yield was 60.5%. Elemental analysis structure (molecular formula C 18 h 20 BClO 2 ): theoretical value C, 68.72; H, 6.41; B, 3.44; Cl, ​​11.27; O, 10.17; test value: C, 68.75; ESI-MS(m / z)(M + ): The theoretical value is 314.12, and the measured value is 314.16.

[0068] (2) Weigh 11.11mol of intermediate H-2 and 7.40mol of raw material I-11, and dissolve it in a mixed solution of toluene / water / ethanol with a volume ratio of 3:1:1; then add 0.012mol of Pd(OAc) 2 , 7.21 mmol Cs 2 CO ...

Embodiment 3

[0073] Embodiment 3: the synthesis of compound 1

[0074]

[0075] The specific preparation method is as follows: in a 250ml three-necked flask, under an atmosphere of nitrogen gas, add 0.01mol of intermediate A-1, 0.012mol of raw material I-1, 0.03mol of potassium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol triphenylphosphine, 150ml toluene, heated and refluxed for 12 hours, sampled and spotted, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product; HPLC purity 98.7%, yield 85.9%; elemental analysis Structure (molecular formula C 37 h 21 NO 3 ): theoretical value C, 84.24; H, 4.01; N, 2.65; O, 9.10; test value: C, 84.26; H, 4.02; N, 2.64; ESI-MS (m / z) (M+): theoretical value 527.15, found value 527.18.

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Abstract

The invention discloses an organic compound taking a carbazole derivative as a core as well as a preparation method and application of the same, and belongs to the technical field of semiconductors. The organic compound has the structure that is shown as a general formula (1); the invention further discloses a preparation method and application of the compound. The compound provided by the invention has relatively high glass transition temperature and molecular thermal stability, proper HOMO and LUMO energy levels and relatively high Eg; by optimizing the device structure, the photoelectric property of the OLED device can be effectively improved, and the service life of the OLED device can be effectively prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an organic compound with a carbazole derivative as the core and its application in an organic electroluminescence device. 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. OLED light-emitting devices are current devices. When a voltage is applied to the electrodes at both ends, ...

Claims

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Application Information

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IPC IPC(8): C07D491/153C07D495/14C07D405/04C07D209/94C07D487/14C07D519/00C07D495/04C07D471/04C07D401/14C07D401/10C07D405/14C07D491/052C07D471/14C07D409/04C07D405/10C07D491/048C07D409/14C07D491/147C07D491/22C07D471/22C09K11/06H01L51/50H01L51/54
CPCC07D491/153C07D495/14C07D405/04C07D209/94C07D519/00C07D495/04C07D471/04C07D487/14C07D401/14C07D401/10C07D405/14C07D491/052C07D471/14C07D409/04C07D405/10C07D491/048C07D409/14C07D491/147C07D491/22C07D471/22C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1088C09K2211/1092H10K85/615H10K85/654H10K85/6576H10K85/657H10K85/6574H10K85/6572H10K50/11
Inventor 李崇叶中华梁丽王芳
Owner JIANGSU SUNERA TECH CO LTD
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