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A'-pi-A-pi-A' type organic small molecule and preparation method and application thereof

A small molecule, organic technology for use in solar cells

Active Publication Date: 2019-04-12
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few reports on donor materials for organic small molecule solar cells based on TPTI units, especially the weakly electron-withdrawing TPTI unit as the central core (A), and electron-withdrawing units (such as 1.3-indanedione or 3- Ethyl rhodanine, etc.) as the terminal (A'), the aromatic heterocyclic unit is the A'-π-A-π-A' type organic small molecule donor material of the π conjugated bridge, its preparation method and photovoltaic application Not yet reported

Method used

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  • A'-pi-A-pi-A' type organic small molecule and preparation method and application thereof
  • A'-pi-A-pi-A' type organic small molecule and preparation method and application thereof
  • A'-pi-A-pi-A' type organic small molecule and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0092] An A′-π-A-π-A′-type small molecule CS6 based on TPTI units, with a weakly electron-withdrawing TPTI unit as the central core A, 3-hexylthiophene as the π-conjugated bridge, and 1,3-indane The diketone is the electron-withdrawing terminal A'.

[0093] CS6 has the general structural formula of formula I:

[0094]

[0095] Wherein, R is 2-octyldodecyl, R 1 is n-hexyl, A' is 1,3-indandione.

[0096] The specific chemical structural formula of CS6 is:

[0097]

[0098] A preparation method of CS6 of this embodiment, see the synthetic route figure 1 , the specific preparation method comprises the following steps:

[0099] (1) 2,5-Dibromo-N 1 ,N 4 -Bis(2-octyldodecyl)-N 1 ,N 4 - Synthesis of bis(thiophen-3-yl)terephthalamide (compound 3).

[0100] 1.1. Under argon atmosphere, in a 250mL three-necked flask, add 11.6g (30.56mmol) N-(2-octyldodecyl)thiophene-3-amine (compound 1), 5mL triethylamine and 40mL dry of dichloromethane.

[0101] 1.2. Dissolve 5 g (13.89...

Embodiment 2

[0159] An A′-π-A-π-A′-type small molecule CS7 based on TPTI units, with a weakly electron-withdrawing TPTI unit as the central core A, 3-hexylthiophene as the π-conjugated bridge, and 3-ethylrhodan Ning is the electron-withdrawing terminal A'.

[0160] CS7 has the general structural formula of formula I:

[0161]

[0162] Wherein, R is 2-octyldodecyl, R 1 is n-hexyl, A' is 3-ethyl rhodanine, and the specific chemical structural formula is as follows:

[0163]

[0164] A preparation method of CS7 of this embodiment, see the synthetic route figure 1 , the specific preparation method comprises the following steps:

[0165] (1) Intermediate M1 (5,5'-(4,10-bis(2-octyldodecyl)-5,11-dioxo4,5,10,11tetrahydrothiophene[2', Synthesis of 3':5,6]pyrido[3,4-g]thieno[3,2-c]isoquinoline-2,8-diyl)bis(3-hexylthiophene-2-carbaldehyde)) : Same as Example 1.

[0166] (2) Synthesis of CS7: as a raw material, under argon atmosphere, add 0.82g of intermediate M1 (0.63mmol) and 0.40g of 3-...

Embodiment 3

[0179] A TPTI unit-based A′-π-A-π-A′-type small molecule CS8: a weakly electron-withdrawing TPTI unit as the central core A, 3,3″-dioctyl-(2,2′:5 ',2″-trithiophene) is the π-conjugated bridge, and 1,3-indandione is the electron-withdrawing terminal A'.

[0180] CS8 has the general structural formula of formula II:

[0181]

[0182] Wherein, R is 2-octyldodecyl, R 1 is n-octyl, A' is 1,3-indanedione, and the specific chemical structural formula of the small molecule CS8 is as follows:

[0183]

[0184] A preparation method of CS8 of this embodiment, see the synthetic route figure 2 , the specific preparation method comprises the following steps:

[0185] (1) Compound 4(4,10-bis(2-octyldodecyl)-4,10-dihydrothieno[2',3':5,6]pyrido[3,4-g] Synthesis of thieno[3,2-c]isoquinoline-5,11-dione): same as Example 1.

[0186] (2) 4,10-bis(2-octyldodecyl)-2,8-bis(trimethylstannyl)-4,10-dihydrothieno[2',3':5, 6] Synthesis of pyrido[3,4-g]thieno[3,2-c]isoquinoline-5,11-dione (int...

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Abstract

The invention provides an A'-pi-A-pi-A' type organic small molecule and a preparation method and application thereof. The A'-pi-A-pi-A' type organic small molecule takes a TPTI unit of a weak withdrawing electron as a central nucleus A, 3-hexylthiophene, 3, 3'-dioctyl-(2, 2': 5', 2'-trithiophene) as a pi conjugated bridge, 1, 3-indandione, 3-ethyl rhodanine as a terminal A' of the weak withdrawingelectron. The preparation method is as follows: an intermediate M1 and an intermediate A' are subjected to Knoevenagel condensation reaction under the action of a solvent and a catalyst. The A'-pi-A-pi-A' type organic small molecule can achieve the regulation and control of the photoelectric performance such as small molecular structure, absorption spectrum, band gap, frontier molecular orbital energy level and the like by changing the pi bridge and different weak withdrawing electron terminals (A'), and the small molecular can prepare a small molecule photoelectric functional material with excellent photoelectric performance, and can be applied to the preparation of solar cells.

Description

technical field [0001] The present invention relates to the technical field of solar cells, in particular to thieno[2′,3′:5.6]pyrido[3,4-g]thieno[3,2-c]-isoquinoline-5,11(4H , 10H)-diketone (abbreviated as TPTI) structural unit A'-π-A-π-A' type organic small molecule and its preparation method and application. Background technique [0002] Small organic molecule solar cell is a device based on small organic molecules that directly converts solar energy into electrical energy by utilizing the photovoltaic effect. It has the advantages of light weight, cheap price, simple preparation process, and good controllability of the chemical structure of the material, and has obvious advantages in future applications. Since the 1990s, after nearly three decades of unremitting efforts, the power conversion efficiency (PCE) of organic solar cells has been steadily improved, showing broad application and research and development prospects. At present, the PCE of acceptor-donor-acceptor ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/22H01L51/42H01L51/46
CPCC07D495/22H10K85/6576H10K85/657H10K30/00Y02E10/549
Inventor 沈平陈龙尹攀曾小英
Owner XIANGTAN UNIV
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