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Triarylamine organic compound containing dibenzofuran and application thereof

An organic compound, dibenzofuran-based technology, applied to triarylamine organic compounds and their application in electroluminescent devices, can solve problems such as differences, improve current efficiency and life, improve migration rate, improve The effect of carrier mobility

Active Publication Date: 2021-07-20
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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  • Triarylamine organic compound containing dibenzofuran and application thereof
  • Triarylamine organic compound containing dibenzofuran and application thereof
  • Triarylamine organic compound containing dibenzofuran and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Embodiment 1: the synthesis of compound 10

[0070]

[0071] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol intermediate N-1, 0.012mol raw material D-1, 150ml toluene and stir to mix, then add 5×10 -5 mol Pd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylphosphine, 0.03mol of sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampling plate, showed no remaining bromide, and the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated until there was no distillate , through a neutral silica gel column to obtain the target product with a purity of 99.8% and a yield of 87.3%.

[0072] Elemental analysis structure (molecular formula C 56 h 35 NO 2 ): theoretical value C, 89.22; H, 4.68; N, 1.86; O, 4.24; test value: C, 89.17; H, 4.70; N, 1.89. LC-MS (m / z) (M+): theoretical value 753.27, found value 753.35.

[0073] 1 H NMR (500MHz, Chloroform-d) δ8.05-7.94 (m, 5H), 7.94-7.86 (m...

Embodiment 2

[0074] Embodiment 2: the synthesis of compound 12

[0075]

[0076] The synthesis steps of compound 12 are similar to those of compound 10, except that raw material D-1 is replaced by raw material D-2;

[0077] Elemental analysis structure (molecular formula C 62 h 39 NO 2 ): theoretical value C, 89.72; H, 4.74; N, 1.69; O, 3.86; test value: C, 89.66; H, 4.75; N, 1.72. LC-MS (m / z) (M+): theoretical value 829.30, found value 829.21.

[0078] 1 H NMR (500MHz, Chloroform-d) δ8.00 (ddd, J = 13.4, 7.4, 1.5Hz, 4H), 7.96-7.90 (m, 3H), 7.89-7.81 (m, 2H), 7.80 (ddd, J =4.8, 3.8, 1.5Hz, 1H), 7.80-7.74(m, 2H), 7.63-7.54(m, 8H), 7.50(t, J=7.5Hz, 1H), 7.50-7.44(m, 7H), 7.46-7.36(m, 4H), 7.38(s, 1H), 7.39-7.33(m, 1H), 7.25(d, J=1.5Hz, 1H), 7.23-7.16(m, 4H).

Embodiment 3

[0079] Embodiment 3: the synthesis of compound 93

[0080]

[0081] The synthesis steps of compound 93 are similar to those of compound 10, except that intermediate N-1 is replaced by intermediate N-2, and raw material D-1 is replaced by raw material D-3;

[0082] Elemental analysis structure (molecular formula C 58 h 37 NO 2 ): theoretical value C, 89.32; H, 4.78; N, 1.80; O, 4.10; test value: C, 89.27; H, 4.79; N, 1.83. LC-MS: theoretical value 779.28, found value 779.24.

[0083] 1 H NMR (500MHz, Chloroform-d) δ8.05-7.97(m, 4H), 7.92(d, J=1.5Hz, 1H), 7.87-7.75(m, 4H), 7.66(d, J=1.5Hz, 1H), 7.62-7.56(m, 5H), 7.56-7.24(m, 19H), 7.24-7.18(m, 2H), 7.16(dt, J=7.5, 1.5Hz, 1H).

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PUM

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Abstract

The invention relates to a triarylated amine organic compound containing dibenzofuran and application thereof, and belongs to the technical field of semiconductors, according to the organic compound provided by the invention, a specific branch chain is introduced on the basis of the existing dibenzofuran and arylated amine group combined compound, so that intermolecular electron cloud overlapping becomes larger, and the coupling between molecular orbits becomes stronger; the larger the overlapping of intermolecular electron clouds is, the easier the jumping process occurs, so that the carrier mobility is effectively improved, the invention also discloses application of the compound, the compound provided by the invention has relatively strong hole transport capability, can play a role in electron blocking under proper HOMO energy level and LUMO energy level, and the recombination efficiency of excitons in the light-emitting layer is improved.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a triarylamine organic compound containing dibenzofuran and its application in electroluminescent devices. Background technique [0002] Organic electroluminescence (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-emitting device, and the...

Claims

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Application Information

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IPC IPC(8): C07D307/91H01L51/54H01L51/50
CPCC07D307/91H10K85/636H10K85/626H10K85/633H10K85/631H10K85/615H10K85/6574H10K50/18Y02E10/549
Inventor 赵四杰王芳李崇张兆超
Owner JIANGSU SUNERA TECH CO LTD