Nitrogen-containing compound and electronic component and electronic device using same

A nitrogen compound, chemical formula technology, applied in the field of organic light-emitting materials

Active Publication Date: 2021-05-07
SHAANXI LIGHTE OPTOELECTRONICS MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there are still problems in the performance of organic electroluminescent devices that need to be further improved, especia

Method used

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  • Nitrogen-containing compound and electronic component and electronic device using same
  • Nitrogen-containing compound and electronic component and electronic device using same
  • Nitrogen-containing compound and electronic component and electronic device using same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0168] In order to illustrate the specific synthesis implementation method of each compound, the following is an example of the specific synthesis method of some compounds in the compounds of the present invention:

[0169] 1. Synthesis of Intermediate 1 (Intermediate 1-A-1 to 1-A-10)

[0170] (1) Synthesis of Intermediate 1-A-1

[0171] S1, the connection between material 1 (Substance 1) and material 2 (Substance 2) (Formula A")

[0172]

[0173] 2-Bromo-3-chloro-1-iodobenzene (190.4g, 600mmol), m-aminophenylboronic acid (90.38g, 660mmol), tetrakis(triphenylphosphine palladium) (3.467g, 3mmol), potassium carbonate (165.852 g, 1200mmol), tetrabutylammonium bromide (3.87g, 12mmol), toluene (1140mL), ethanol (380mL) and deionized water (380mL) were added in a round bottom flask, heated to 78°C under nitrogen protection, and stirred for 6 Hour; the reaction solution was cooled to room temperature, added toluene (1100mL) for extraction, the combined organic phases were dried ...

Synthetic example 1

[0195] Synthesis of S5, Intermediate 3 (Formula C)

[0196] Synthesis of Intermediate 1-C-1

[0197]

[0198] Intermediate 1-B-1 (32.96g, 60.73mmol), bromobenzene (9.53g, 60.73mmol), tris(dibenzylideneacetone) dipalladium (0.556g, 0.607mmol), 2-dicyclohexylphosphine -2',4',6'-triisopropylbiphenyl (0.579g, 1.21mmol) and sodium tert-butoxide (8.75g, 91.09mmol) were added to toluene (330mL), heated to 108°C under nitrogen protection, Stir for 1 h, then cool to room temperature, wash the reaction solution with water, add magnesium sulfate to dry, filter and remove the solvent from the filtrate under reduced pressure; use dichloromethane / n-heptane system to recrystallize and purify the crude product to obtain off-white solid intermediate 1 -c-1 (31.56g, yield 84%).

[0199] Synthesis of S6, compound (Formula 1)

[0200]

[0201] Intermediate 1-c-1 (31.56g, 51mmol), 4-bromobiphenyl (11.89g, 51mmol), three (dibenzylideneacetone) dipalladium (0.467g, 0.51mmol), 2-dicyclohexyl...

Synthetic example 2-22

[0203] The compound shown in table 3 is prepared with reference to the method for synthetic example 1, difference is, replace intermediate 1-B-1 with intermediate 2 in table 3, replace bromobenzene with raw material 4 (Substance 4), raw material 5 (Substance 5) Instead of 4-bromobiphenyl. The raw materials used and the corresponding synthesized compounds, the yield of the last step, and the mass spectrometry characterization results of the compounds are shown in Table 3:

[0204] table 3

[0205]

[0206]

[0207]

[0208]

[0209]

[0210] NMR of compound 213: 1 H NMR (400Hz, CDCl 3 ):8.62(d,1H),8.59(d,1H),8.23-8.20(d,2H),8.12(d,1H),8.07-8.02(m,4H),7.95-7.78(m,17H), 7.70-7.60(m,5H),7.45-7.35(m,4H),7.12(d,1H),2.90(d,2H),2.56(d,2H),2.16(s,1H),1.94-1.93( m,3H), 1.76(d,2H), 1.67(d,2H), 1.56(s,2H).

[0211] NMR of compound 354: 1 H NMR (400Hz, CDCl 3 ):8.56(d,1H),8.20(d,1H),8.12(s,1H),8.07-8.02(m,4H),7.85-7.68(m,16H),7.65-7.53(m,9H), 7.45-7.35(m,4H),2.90(d,2...

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Abstract

The invention belongs to the field of organic light-emitting materials, and particularly relates to a nitrogen-containing compound and an electronic element and an electronic device using the same, and the nitrogen-containing compound has a structure as shown in a chemical formula 1. When the nitrogen-containing compound is applied to the organic electroluminescent device, the performance of the device can be effectively improved.

Description

technical field [0001] The application belongs to the technical field of organic luminescent materials, and specifically provides a nitrogen-containing compound and electronic components and electronic devices using the same. Background technique [0002] With the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is becoming wider and wider. Such electronic components generally include a cathode and an anode oppositely arranged, and a functional layer arranged between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers, and generally includes an energy conversion layer, a hole transport layer located between the energy conversion layer and the anode, and an electron transport layer located between the energy conversion layer and the cathode. [0003] Taking an organic electroluminescent dev...

Claims

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Application Information

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IPC IPC(8): C07D405/12C07D209/86C07D405/10C07D409/10C07D401/12C07D471/04C09K11/06H01L51/54
CPCC07D209/86C07D405/10C07D409/10C07D401/12C07D405/12C07D471/04C09K11/06C09K2211/1029C09K2211/1088C09K2211/1092C09K2211/1044H10K85/624H10K85/6576H10K85/6574H10K85/6572Y02E10/549
Inventor 肖蛟李昕轩
Owner SHAANXI LIGHTE OPTOELECTRONICS MATERIAL CO LTD
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