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Triarylamine organic compound taking carbazole as core and application of triarylamine organic compound

A technology for organic compounds and triarylamines, applied in the field of triarylamine organic compounds, can solve problems such as differences, and achieve the effects of reducing the influence of deformation, improving the utilization rate of excitons, and improving the composite efficiency.

Active Publication Date: 2021-03-26
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 taking carbazole as core and application of triarylamine organic compound
  • Triarylamine organic compound taking carbazole as core and application of triarylamine organic compound
  • Triarylamine organic compound taking carbazole as core and application of triarylamine organic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1: the synthesis of intermediate B1:

[0045]

[0046] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material 1-1, 0.012mol raw material 2-1, 150ml toluene and stir to mix, then add 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol P(t-Bu) 3 , 0.03mol sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampled on a plate, and 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, and the target product intermediate was obtained B1; HPLC purity 99.37%, yield 73.4%; Elemental analysis structure (molecular formula C 34 h 23 NO): Theoretical C, 88.48; H, 5.02; N, 3.03; Tested: C, 88.45; H, 5.01; N, 3.01. ESI-MS (m / z) (M+): The theoretical value is 461.18, and the measured value is 461.21.

[0047] The synthetic raw materials of intermediate B required in the embodiment are shown in Table 1:

[0048] Table 1 ...

Embodiment 2

[0052] Embodiment 2: the synthesis of intermediate C1:

[0053]

[0054] Under nitrogen atmosphere, add 0.01mol raw material 3-1, 0.025mol raw material 4-1, 0.03mol sodium tert-butoxide, 5×10 -5 mol Pd 2 (dba) 3 and 5×10 -5 mol of tri-tert-butylphosphine, then add 150ml of toluene to dissolve it, heat to 100°C, reflux for 24 hours, observe the reaction by TLC until the reaction is complete. Naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated until there was no fraction. The resulting material was purified by silica gel column (petroleum ether as eluent) to obtain intermediate C-1. HPLC purity 98.18%, yield 82.6%; Elemental analysis structure (C 34 h 20 BrN) Theoretical: C, 78.17; H, 3.86; Br, 15.29; N, 2.68; Found: C, 78.17; H, 3.86; Br, 15.29; N, 2.68. ESI-MS (m / z) (M+): The molecular weight of the material is 521.08, and the measured molecular weight is 521.27.

[0055] The synthetic raw materials of intermediate C required in th...

Embodiment 3

[0058] Embodiment 3: the synthesis of compound 14:

[0059]

[0060] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol intermediate B1, 0.012mol intermediate C1, 150ml toluene and stir to mix, then add 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol P(t-Bu) 3 , 0.03mol sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampled and plated, 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, and the target product was obtained, HPLC The purity is 99.63%, and the yield is 79.4%. Elemental analysis structure (molecular formula C 68 h 42 N 2 O): Theoretical: C, 90.44; H, 4.69; N, 3.10; Tested C, 90.47; H, 4.65; N, 3.12. ESI-MS (m / z) (M+): Calculated 902.33, found 902.39. 1 H NMR (500MHz, Chloroform-d) δ8.22(dt,1H),8.17–8.10(m,2H),8.06–7.94(m,8H),7.87–7.76(m,3H),7.76(dt,1H ),7.69(d,1H),7.67–7.53(m,9H),7.53–7.37(m,7H),7.37–7.31(m...

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Abstract

The invention relates to a triarylamine organic compound taking carbazole as a core and application of the triarylamine organic compound, and belongs to the technical field of semiconductors. The structure of the compound provided by the invention is shown as a general formula (I) (See the specification). The invention also discloses application of the compound. The compound provided by the invention has a relatively strong electron blocking effect, and improves the recombination efficiency of excitons in a light-emitting layer. When the compound is used as a light-emitting functional layer material of an OLED light-emitting device, the exciton utilization rate and the radiation efficiency can be effectively improved by matching with the branched chains in the range of the invention.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a triarylamine organic compound with carbazole as the core and an application thereof. Background technique [0002] At present, OLED display technology has been applied in smart phones, tablet computers and other fields, and will further expand to large-size applications such as TVs. However, compared with actual product application requirements, the luminous efficiency and service life of OLED devices Further improvement is required. Research on improving the performance of OLED light-emitting devices includes: reducing the driving voltage of the device, improving the luminous efficiency of the device, and increasing the service life of the device. In order to realize the continuous improvement of the performance of OLED devices, not only the innovation of OLED device structure and manufacturing process is required, but also the continuous research and innovation of OLE...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C07D405/12C07D409/12H01L51/50H01L51/54
CPCC07D209/86C07D405/12C07D409/12H10K85/626H10K85/615H10K85/6576H10K85/6574H10K85/6572H10K50/00Y02E10/549
Inventor 王芳陆颖李崇
Owner JIANGSU SUNERA TECH CO LTD
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