A kind of fused ring non-fullerene acceptor material and its preparation method and application

A non-fullerene acceptor and fused ring technology, applied in the field of electrochemical materials, can solve problems such as limiting the light absorption capacity of materials, achieve high electron mobility, high short-circuit current and energy conversion efficiency, and increase the effect of electron cloud density

Active Publication Date: 2019-08-20
THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Since the band gap and light-absorbing ability of the material mainly depend on the push-pull effect between the electron-donating unit and the electron-withdrawing unit, this means that the more general electron-donating ability of the carbon bridge trapezoidal unit will become a bottleneck that limits the further improvement of the material’s light-absorbing ability.

Method used

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  • A kind of fused ring non-fullerene acceptor material and its preparation method and application
  • A kind of fused ring non-fullerene acceptor material and its preparation method and application
  • A kind of fused ring non-fullerene acceptor material and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0109] In this example, a fused-ring non-fullerene acceptor material as shown in the structure of formula I is prepared by the following steps, named NFA1, wherein R is Ar 1 for Ar 2 for The donor of the EG group is Specific steps are as follows:

[0110] (1) Compound a1 and compound b1 are coupled under catalyst catalysis to generate compound c1:

[0111]

[0112] In a 100mL Schlenck tube, sequentially add brominated raw material a1 (950 mg), tin-substituted raw material b1 (746 mg), Pd (PPh 3 ) 4 (164mg), toluene (50mL), DMF (3.8mL), heated to reflux under nitrogen protection for 48 hours, removed the toluene by rotary evaporation under reduced pressure and passed through a silica gel column with chloroform as the eluent to obtain a yellow solid product c1 (774mg, produced rate 89%).

[0113] NMR and mass spectrometry data of c1: 1 H NMR (CDCl 3 ,400MHz,δ / ppm):7.49(d,J=5.3Hz,2H),7.26(d,J=5.3Hz,2H),4.38(q,J=7.1Hz,4H),4.02(s,6H) ,1.35(t,J=7.1Hz,6H). 13 C NMR...

Embodiment 2

[0135] In this example, a fused-ring non-fullerene acceptor material as shown in the formula II structure is prepared by the following steps, named NFA2, wherein R is Ar 1 for Ar 2 for The donor of the EG group is Specific steps are as follows:

[0136] (a) Compound a1' and compound b1' are coupled under catalyst catalysis to generate compound c1':

[0137]

[0138] Add tin-substituted raw material a1' (4.7g), brominated raw material b1' (2.8g), Pd(PPh 3 ) 4 (890mg), toluene (50mL), heated to reflux under nitrogen protection for 40 hours, removed the toluene by rotary evaporation under reduced pressure, and passed through a silica gel column with dichloromethane as the eluent to obtain the yellow solid product c1' (2.5g, yield 74 %). Mass spectral data of c1': MALDI-TOFMS (m / z): 446.2 (M + ).

[0139] (b) Compound c1' reacts with boron tribromide at room temperature to generate compound d1':

[0140]

[0141] In a 100mL Schlenck tube, add c1' (446mg), dry ...

Embodiment 3

[0159] In this example, a fused ring non-fullerene acceptor material with the structure shown in formula I was prepared by the following steps, named NFA3, wherein R is C 8 straight chain alkyl, Ar 1 for Ar 2 for The donor of the EG group is Specific steps are as follows:

[0160] (1) Compound a2 and compound b2 are coupled under catalyst catalysis to generate compound c2:

[0161]

[0162] Into a 100mL Schlenck tube, add brominated raw material a2 (330mg), tin-substituted raw material b2 (212mg), Pd(PPh 3 ) 4 (50mg), toluene (15mL), DMF (1mL), heated to reflux under nitrogen protection for 60 hours, decompressed and rotary evaporated to remove toluene, and passed through a silica gel column, with chloroform as eluent, to obtain yellow solid product c2 (219mg, yield 71%). Mass spectrometry data of c2: MALDI-TOF MS(m / z): 671.0(M + ).

[0163] (2) Compound c2 reacts with boron tribromide at room temperature to generate compound d2:

[0164]

[0165] In a 100m...

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Abstract

The invention provides a fused-ring non-fullerene acceptor material and its preparation method and application. The fused-ring non-fullerene acceptor material includes an electron-donating unit and an electron-withdrawing terminal group, and the electron-donating unit is a carbon-oxygen Bridge-ladder fused ring structure, the electron-withdrawing end group is connected to both ends of the electron-donating unit, and the fused-ring non-fullerene acceptor material has a structure shown in formula I or formula II, through the preparation method of the present invention The prepared fused-ring non-fullerene acceptor material has excellent light absorption and carrier transport properties, is easily soluble in common organic solvents, has strong visible and near-infrared light absorption properties, and high electron mobility (≥10 ‑5 cm 2 ·V ‑1 ·s ‑1 ), which can achieve high short-circuit current and energy conversion efficiency in organic solar cells, and has broad application prospects and high application value.

Description

technical field [0001] The invention belongs to the field of electrochemical materials, and relates to a condensed-ring non-fullerene acceptor material and a preparation method and application thereof. Background technique [0002] Organic solar cells, which use organic conjugated molecules as active materials, have many advantages such as light weight, flexibility, wide source of raw materials, solution processing and large-area preparation, etc., and have become one of the focuses of global academic and industrial circles in recent years. The development and continuous progress of conjugated molecular materials is the driving force for the performance improvement of organic solar cells. At present, many types of organic conjugated compounds, including conjugated polymers, conjugated small molecules, and fullerenes, have been applied to the active layer of the battery. Among many materials, ladder-shaped conjugated molecular materials based on carbon atoms as bridges have e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/22C07D519/00H01L51/42H01L51/46
CPCC07D495/22C07D519/00H10K85/657H10K30/00Y02E10/549
Inventor 丁黎明肖作
Owner THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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