Organic photoelectric material with boron bridged 2,2'-dithiophene structure and application of organic photoelectric material

Abstract

The invention relates to an organic photoelectric material with a boron bridged 2,2'-dithiophene structure and an application of the organic photoelectric material, and belongs to the field of organicphotoelectric materials. According to the organic photoelectric material provided by the invention, boron bridged 2,2'-dithiophene is adopted as a parent body, so that the molecular stability is greatly improved, the electron affinity and conductivity are improved, and the transmission of electrons is facilitated; aromatic amines with good hole transmission properties are combined, so that the photoelectric material with bipolar transmission capability is formed, the transmission of holes and electrons in a light-emitting layer is balanced, and the luminous efficiency is greatly improved; theorganic photoelectric material containing the boron bridged 2,2'-dithiophene structure provided by the invention has a space structure of a rigid trapezoidal plane structure, so that the molecular potential barrier is reduced, and the electron affinity is improved; and the organic photoelectric material is used as a light-emitting material of an organic light emitting diode (OLED) light-emittingdevice, the produced OLED device has the effect characteristics of high brightness, high efficiency and a low voltage.

Description

technical field

[0001] The invention relates to the field of organic photoelectric materials, in particular to an organic photoelectric material containing a boron-bridged dithiophene structure and an application thereof. Background technique

[0002] Organic Light Emitting Diode (OLED) is known as the most promising "dream" display technology in the 21st century due to its characteristics of self-luminescence, wide viewing angle, fast response and simple manufacturing process. The electroluminescent mechanism of OLED is that after electrons and holes are respectively injected from the cathode and anode, they combine in the light-emitting molecules through the multi-layer organic functional layer between the two electrodes to form excitons, and the excitons radiate and decay to emit light. However, because the mobility of electrons and holes in organic materials is usually difficult to equalize, it is easy to cause carrier imbalance and ultimately affect the efficiency and l...

Examples

Embodiment 1

[0049] Embodiment 1. Preparation of organic optoelectronic materials

Embodiment 11

[0050] The synthesis of embodiment 11 compound 1:

[0051] Dissolve 3,3'-dibromo-5,5'-di-tert-butyl-2,2'-bithiophene (4.36g, 10.0mmol) in 100mLTHF, cool down to -70°C, add n-butyllithium dropwise n-Hexane solution (12mL, 2.0mol / L), after the dripping, keep warm for 1.0hrs. Control the internal temperature to less than -70°C, add a THF solution of 4-(boron dichloride)-N,N-diphenylamine aniline (3.5g, 11mmol, 0.1mol / L) dropwise, and keep it warm for 3.0hrs after the dropping , slowly warming up to room temperature, poured into 100g saturated aqueous sodium chloride solution, layered, the organic phase was washed with saturated aqueous sodium chloride solution, dried, and desolvated to obtain 5.6g of a brown-yellow viscous liquid. Recrystallized using n-hexane to obtain off-white solid particles (2.9 g, yield 54.61%). Using DEI-MS to identify the compound, formula C 34 h 34 BNS 2 , detection value [M+1] + =532.49, calculated value 531.58.

Embodiment 12

[0052] The synthesis of embodiment 12 compound 2:

[0053] Dissolve 3,3'-dibromo-5,5'-di-tert-butyl-2,2'-bithiophene (4.36g, 10.0mmol) in 100mLTHF, cool down to -70°C, add n-butyllithium dropwise n-Hexane solution (12mL, 2.0mol / L), after the dripping, keep warm for 1.0hrs. Control the internal temperature to less than -70°C, add 4-(boron dichloride)-N,N-bis(4-isopropylphenyl)aniline THF solution (4.5g, 11mmol, 0.1mol / L) dropwise, drop After completion, keep the reaction for 3.0 hrs, slowly warm up to room temperature, pour into 100 g of saturated aqueous sodium chloride solution, separate layers, wash the organic phase with saturated aqueous sodium chloride solution, dry, and remove the solvent to obtain 6.5 g of brown-yellow viscous liquid. Recrystallized using n-hexane to obtain off-white solid particles (3.4 g, yield 55.28%). Using DEI-MS to identify the compound, formula C 40 h 46 BNS 2 , detection value [M+1] + =615.79, calculated value 615.74.

[0054] Compounds 1...

technical field

[0001] The invention relates to the field of organic photoelectric materials, in particular to an organic photoelectric material containing a boron-bridged dithiophene structure and an application thereof. Background technique

[0002] Organic Light Emitting Diode (OLED) is known as the most promising "dream" display technology in the 21st century due to its characteristics of self-luminescence, wide viewing angle, fast response and simple manufacturing process. The electroluminescent mechanism of OLED is that after electrons and holes are respectively injected from the cathode and anode, they combine in the light-emitting molecules through the multi-layer organic functional layer between the two electrodes to form excitons, and the excitons radiate and decay to emit light. However, because the mobility of electrons and holes in organic materials is usually difficult to equalize, it is easy to cause carrier imbalance and ultimately affect the efficiency and l...

Examples

Embodiment 1

[0049] Embodiment 1. Preparation of organic optoelectronic materials

Embodiment 11

[0050] The synthesis of embodiment 11 compound 1:

[0051] Dissolve 3,3'-dibromo-5,5'-di-tert-butyl-2,2'-bithiophene (4.36g, 10.0mmol) in 100mLTHF, cool down to -70°C, add n-butyllithium dropwise n-Hexane solution (12mL, 2.0mol / L), after the dripping, keep warm for 1.0hrs. Control the internal temperature to less than -70°C, add a THF solution of 4-(boron dichloride)-N,N-diphenylamine aniline (3.5g, 11mmol, 0.1mol / L) dropwise, and keep it warm for 3.0hrs after the dropping , slowly warming up to room temperature, poured into 100g saturated aqueous sodium chloride solution, layered, the organic phase was washed with saturated aqueous sodium chloride solution, dried, and desolvated to obtain 5.6g of a brown-yellow viscous liquid. Recrystallized using n-hexane to obtain off-white solid particles (2.9 g, yield 54.61%). Using DEI-MS to identify the compound, formula C 34 h 34 BNS 2 , detection value [M+1] + =532.49, calculated value 531.58.

Embodiment 12

[0052] The synthesis of embodiment 12 compound 2:

[0053] Dissolve 3,3'-dibromo-5,5'-di-tert-butyl-2,2'-bithiophene (4.36g, 10.0mmol) in 100mLTHF, cool down to -70°C, add n-butyllithium dropwise n-Hexane solution (12mL, 2.0mol / L), after the dripping, keep warm for 1.0hrs. Control the internal temperature to less than -70°C, add 4-(boron dichloride)-N,N-bis(4-isopropylphenyl)aniline THF solution (4.5g, 11mmol, 0.1mol / L) dropwise, drop After completion, keep the reaction for 3.0 hrs, slowly warm up to room temperature, pour into 100 g of saturated aqueous sodium chloride solution, separate layers, wash the organic phase with saturated aqueous sodium chloride solution, dry, and remove the solvent to obtain 6.5 g of brown-yellow viscous liquid. Recrystallized using n-hexane to obtain off-white solid particles (3.4 g, yield 55.28%). Using DEI-MS to identify the compound, formula C 40 h 46 BNS 2 , detection value [M+1] + =615.79, calculated value 615.74.

[0054] Compounds 1...

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