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Compounds, organic photoelectric device and electronic device

A technology for organic optoelectronic devices and electronic equipment, applied in the field of organic optoelectronic devices, electronic equipment, and compounds, can solve problems such as performance to be improved, and achieve the effects of reducing device voltage, improving device efficiency, and improving luminous efficiency

Active Publication Date: 2019-09-20
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, few TADF materials have been found so far, and the performance needs to be improved.

Method used

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  • Compounds, organic photoelectric device and electronic device
  • Compounds, organic photoelectric device and electronic device
  • Compounds, organic photoelectric device and electronic device

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0104] This synthesis example provides the preparation method of compound M1, specifically as follows:

[0105]

[0106] (1) Add 13.75g (50mmol) of compound A, 150mL of DCM and 5g (50mmol) of triethylamine in a 250mL three-necked flask in sequence, cool down to 0°C in an ice bath, and slowly drop in 50mL of DCM dissolved in a constant pressure dropping funnel. 10.31g (50mmol) of compound B, after the dropwise addition, was raised to room temperature and stirred, and TCL was used to monitor the reaction progress. After the reaction was complete, it was quenched by adding ice water, extracted with DCM, combined the organic phases, removed the solvent, and recrystallized from Tol / EtOH to obtain product C.

[0107] 1 H NMR (400MHz, Chloroform) δ: 8.02(d, J=7.3Hz, 2H), 7.77(s, 1H), 7.43(d, J=12.0Hz, 3H), 7.29(s, 1H), 7.04(s , 1H), 6.89(s, 1H), 6.21(s, 1H), 5.53(s, 1H), 4.31(s, 1H), 3.68(s, 1H).

[0108] 13 C NMR (100MHz, Chloroform) δ: 169.66(s), 140.32(s), 138.21(s), 136.11...

Synthetic example 2

[0119] This synthesis example provides the preparation method of compound M2, specifically as follows:

[0120]

[0121]

[0122] (1) Add 13.75g (50mmol) of compound A, 150mL of DCM and 5g (50mmol) of triethylamine in a 250mL three-necked flask in sequence, cool down to 0°C in an ice bath, and slowly drop in 50mL of DCM dissolved in a constant pressure dropping funnel. 9.95g (50mmol) of compound B, after the dropwise addition, was stirred at room temperature, and the reaction progress was monitored by TCL. After the reaction was complete, it was quenched by adding ice water, extracted with DCM, combined the organic phases, removed the solvent, and recrystallized from Tol / EtOH to obtain product C.

[0123] 1 H NMR (400MHz, Chloroform) δ: δ7.63(s, 1H), 6.80(s, 1H), 6.60(s, 2H), 6.06(s, 1H), 5.18(s, 1H), 4.65(s, 1H), 3.63(s, 1H), 2.26(s, 3H), 2.13(s, 6H).

[0124] 13 C NMR (100MHz, Chloroform) δ: 169.66(s), 139.71(s), 138.90(s), 137.92(s), 135.96(s), 128.27(s), 126.77(s...

Synthetic example 3

[0135] This synthesis example provides the preparation method of compound M3, specifically as follows:

[0136]

[0137] (1) Add 13.75g (50mmol) of compound A, 150mL of DCM and 5g (50mmol) of triethylamine in a 250mL three-necked flask in sequence, cool down to 0°C in an ice bath, and slowly drop in 50mL of DCM dissolved in a constant pressure dropping funnel. 11.66g (50mmol) of compound B, after the dropwise addition was completed, rose to room temperature and stirred, and TCL monitored the reaction progress. After the reaction was complete, it was quenched by adding ice water, extracted with DCM, combined the organic phases, removed the solvent, and recrystallized from Tol / EtOH to obtain product C.

[0138] 1 H NMR (400MHz, Chloroform) δ: 8.35(s, 2H), 7.75(s, 4H), 7.49(s, 3H), 7.40(d, J=8.0Hz, 6H), 6.85(s, 2H), 6.37 (s, 4H), 6.14(s, 2H), 5.51(s, 2H), 4.71(s, 2H), 3.75(s, 2H).

[0139] 13 C NMR (100MHz, Chloroform) δ: 169.66(s), 140.75(s), 140.35(s), 138.01(s), 135.12(...

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Abstract

The invention relates to compounds, an organic photoelectric device and an electronic device. The compounds have a structure represented by a formula (I). The organic photoelectric device comprises an anode, a cathode, and an organic thin layer arranged between the anode and the cathode. The organic thin layer comprises any one of the compounds or at least two of the compounds. The electronic device comprises the organic photoelectric device. The provided compounds have a TADF characteristic; the transition of conventional fluorescence molecules is forbidden to obtain triplet exciton to give off light, and thus the device has high light emission efficiency and a low work voltage.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence materials, in particular to a compound, an organic photoelectric device and electronic equipment. Background technique [0002] Organic light-emitting materials can be roughly divided into four categories according to the light-emitting mechanism: traditional fluorescent materials, phosphorescent materials, triplet-triplet annihilation (TTA) materials, and thermally activated delayed fluorescence (TADF) materials. Among them, the highest internal quantum efficiency of traditional fluorescent materials is only 25%, and the theoretical maximum internal quantum yield of TTA materials does not exceed 62.5%. Although the theoretical maximum internal quantum yield of phosphorescent materials can reach 100%, they usually contain rare and precious metals, resulting in high prices. Expensive, poor device stability, serious device efficiency decline and other issues have further limited ...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06H01L51/54
CPCC07F5/02C09K11/06C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/1092C09K2211/1007C09K2211/1011H10K85/656H10K85/654H10K85/657
Inventor 汪奎
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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