Organic conjugated small molecular material with terminal group containing naphthenic chain as well as preparation method and application thereof in solar cells

Abstract

The invention discloses an organic conjugated small molecular material with a terminal group containing a naphthenic chain as well as a preparation method and application thereof to solar cells, and belongs to the technical field of organic solar cells. The terminal group of the organic conjugated small molecular material contains the naphthenic chain with higher rigidity, so that self-assembly and stacking between molecules are facilitated, the photovoltaic performance of the small molecular material is improved, and the heat stability of the small molecular material is good; moreover, he small molecular material has high light absorption property and has appropriate energy levels and can be dissolved in organic solvents such as chloroform, dichloromethane, tetrahydrofuran and chlorobenzene, and is suitable for being used as an organic solar cell material. The organic conjugated small molecular material disclosed by the invention as a light-captured active layer receptor material is applied to the organic solar cells and has higher photoelectric conversion efficiency.

Description

technical field

[0001] The invention belongs to the technical field of organic solar cells, and in particular relates to an organic conjugated small molecule material with a terminal group containing a cycloalkyl chain, a preparation method thereof, and an application in a solar cell. Background technique

[0002] Polymer solar cells (PCSs) have attracted worldwide attention due to their advantages of light weight, low cost, translucency, solution processing, and large-area roll-to-roll (roll to roll) flexible devices. one of the hotspots. Fullerenes and their derivatives play a vital role in organic solar cell devices due to their multidimensional charge transport properties and easy formation of unique phase separation structures with donor materials. However, due to the narrow wavelength of light absorption of fullerene materials, the difficulty of adjusting the energy level, poor solubility, and high cost, the performance improvement and large-scale use of fullerene as ...

Examples

Embodiment 1

[0053] Synthesis of Compound 5,6,7,8-Tetralindone (2)

[0054] Prepare a 75mL dry pressure-proof bottle, pass argon into it, add compound (1) (3g, 14.9mmol), acetic anhydride (25mL) and triethylamine (15mL) into the pressure-proof bottle successively, under stirring, Ethyl acetoacetate (5.8 mL, 44.6 mmol) was added to the reaction solution, and the reaction was heated to 100° C. for 12 hours after aeration for 20 minutes. Afterwards, the reaction solution was cooled to room temperature, poured into ice water containing HCl (2N), a precipitate was formed, then HCl (5N) (30 mL) was added to the mixed solution, and the mixed solution was heated to reflux, reacted for 3 hours, Afterwards, the reaction was returned to room temperature, and the precipitated solid compound was filtered, washed with water, and dried, and then separated and purified by column chromatography, the eluent was dichloromethane, and the target compound (2) was obtained as a yellow solid. The yield was 66%. ...

Embodiment 2

[0057] Synthesis of Compound 5,6,7,8-tetrahydronaphthalenecyanindanone (HN)

[0058] Prepare a 100mL dry two-necked flask, pass into argon, add compound (2) (2g, 10mmol), malononitrile (2g, 30mmol) and ethanol (30mL) into the reaction flask successively, after stirring evenly, the Sodium acetate (1.1 g, 13 mmol) was added to the reaction solution and stirred at room temperature for 2 hours. Then pour the reaction solution into ice water, add concentrated HCl dropwise to the ice-water mixture, adjust the pH to 1-2, a large amount of precipitate is formed, then filter, wash with water, dry, and then use column chromatography to separate and purify, elute The solvent is dichloromethane, and the obtained product is recrystallized in ethanol to obtain a yellow needle product with a yield of 80%. 1 HNMR (500 MHz, CDCl3, δ): 8.30(s, 1H), 7.66(s, 1H), 3.66(s, 2H), 2.77(d, J=5.0Hz, 4H), 1.89-1.86(m, 4H ). 13 C NMR (125MHz, CDCl3, δ): 194.84, 166.62, 147.54, 147.41, 139.90, 138.20, 1...

Embodiment 3

[0061] Synthesis of Pentacondensed Ring Compound IDT-HN

[0062] Prepare a 100mL dry two-necked flask, pass through argon, add compound IDT-CHO (200mg, 0.21mmol), compound (HN) (155mg, 0.63mmol) and chloroform (30mL) into the reaction flask successively, at room temperature After stirring evenly, 1 mL of pyridine was added dropwise into the reaction liquid, and after aeration for 20 minutes, the reaction was heated to 65° C. for 12 hours. Post-reaction treatment: return the reaction to room temperature, and directly adopt column chromatography for separation and purification. The eluent is dichloromethane. The obtained compound is recrystallized in a mixture of chloroform and methanol to obtain the target compound IDT-HN. The yield 90%. 1 HNMR(500MHz, CDCl3,δ): 8.82(s,2H),8.35(s,2H),7.70(s,2H),7.69(s,2H),7.57(s,2H),7.15-7.11(dd, J=5.0Hz, J=5.0Hz, 16H), 2.92(d, J=5.0Hz, 8H), 2.58(t, J=7.5Hz, 8H), 1.84(s, 8H), 1.63-1.57(m, 8H),1.35-1.29(m,24H),0.87(t,J=7.5Hz,12H). 13 C NMR(1...

technical field

[0001] The invention belongs to the technical field of organic solar cells, and in particular relates to an organic conjugated small molecule material with a terminal group containing a cycloalkyl chain, a preparation method thereof, and an application in a solar cell. Background technique

[0002] Polymer solar cells (PCSs) have attracted worldwide attention due to their advantages of light weight, low cost, translucency, solution processing, and large-area roll-to-roll (roll to roll) flexible devices. one of the hotspots. Fullerenes and their derivatives play a vital role in organic solar cell devices due to their multidimensional charge transport properties and easy formation of unique phase separation structures with donor materials. However, due to the narrow wavelength of light absorption of fullerene materials, the difficulty of adjusting the energy level, poor solubility, and high cost, the performance improvement and large-scale use of fullerene as ...

Examples

Embodiment 1

[0053] Synthesis of Compound 5,6,7,8-Tetralindone (2)

[0054] Prepare a 75mL dry pressure-proof bottle, pass argon into it, add compound (1) (3g, 14.9mmol), acetic anhydride (25mL) and triethylamine (15mL) into the pressure-proof bottle successively, under stirring, Ethyl acetoacetate (5.8 mL, 44.6 mmol) was added to the reaction solution, and the reaction was heated to 100° C. for 12 hours after aeration for 20 minutes. Afterwards, the reaction solution was cooled to room temperature, poured into ice water containing HCl (2N), a precipitate was formed, then HCl (5N) (30 mL) was added to the mixed solution, and the mixed solution was heated to reflux, reacted for 3 hours, Afterwards, the reaction was returned to room temperature, and the precipitated solid compound was filtered, washed with water, and dried, and then separated and purified by column chromatography, the eluent was dichloromethane, and the target compound (2) was obtained as a yellow solid. The yield was 66%. ...

Embodiment 2

[0057] Synthesis of Compound 5,6,7,8-tetrahydronaphthalenecyanindanone (HN)

[0058] Prepare a 100mL dry two-necked flask, pass into argon, add compound (2) (2g, 10mmol), malononitrile (2g, 30mmol) and ethanol (30mL) into the reaction flask successively, after stirring evenly, the Sodium acetate (1.1 g, 13 mmol) was added to the reaction solution and stirred at room temperature for 2 hours. Then pour the reaction solution into ice water, add concentrated HCl dropwise to the ice-water mixture, adjust the pH to 1-2, a large amount of precipitate is formed, then filter, wash with water, dry, and then use column chromatography to separate and purify, elute The solvent is dichloromethane, and the obtained product is recrystallized in ethanol to obtain a yellow needle product with a yield of 80%. 1 HNMR (500 MHz, CDCl3, δ): 8.30(s, 1H), 7.66(s, 1H), 3.66(s, 2H), 2.77(d, J=5.0Hz, 4H), 1.89-1.86(m, 4H ). 13 C NMR (125MHz, CDCl3, δ): 194.84, 166.62, 147.54, 147.41, 139.90, 138.20, 1...

Embodiment 3

[0061] Synthesis of Pentacondensed Ring Compound IDT-HN

[0062] Prepare a 100mL dry two-necked flask, pass through argon, add compound IDT-CHO (200mg, 0.21mmol), compound (HN) (155mg, 0.63mmol) and chloroform (30mL) into the reaction flask successively, at room temperature After stirring evenly, 1 mL of pyridine was added dropwise into the reaction liquid, and after aeration for 20 minutes, the reaction was heated to 65° C. for 12 hours. Post-reaction treatment: return the reaction to room temperature, and directly adopt column chromatography for separation and purification. The eluent is dichloromethane. The obtained compound is recrystallized in a mixture of chloroform and methanol to obtain the target compound IDT-HN. The yield 90%. 1 HNMR(500MHz, CDCl3,δ): 8.82(s,2H),8.35(s,2H),7.70(s,2H),7.69(s,2H),7.57(s,2H),7.15-7.11(dd, J=5.0Hz, J=5.0Hz, 16H), 2.92(d, J=5.0Hz, 8H), 2.58(t, J=7.5Hz, 8H), 1.84(s, 8H), 1.63-1.57(m, 8H),1.35-1.29(m,24H),0.87(t,J=7.5Hz,12H). 13 C NMR(1...

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