A kind of asymmetric a-d-a type conjugated small molecule and its intermediate and application

An A-D-A, asymmetrical technology, applied in the direction of electrical solid-state devices, semiconductor devices, semiconductor/solid-state device manufacturing, etc., can solve problems such as application limitations and difficulties, and achieve high fill factor, high efficiency, and high mobility.

Active Publication Date: 2020-04-10
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the fill factor of organic polymer solar cells based on small molecule acceptor materials with symmetrical structures is generally difficult to exceed 70%, which brings great limitations to practical applications.

Method used

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  • A kind of asymmetric a-d-a type conjugated small molecule and its intermediate and application
  • A kind of asymmetric a-d-a type conjugated small molecule and its intermediate and application
  • A kind of asymmetric a-d-a type conjugated small molecule and its intermediate and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1: Preparation of asymmetric ladder-shaped conjugated compound—compound 1-5 and its asymmetric A-D-A type conjugated small molecule—compound 1:

[0052]

[0053] Synthesis of compound 1-4: under argon protection, compound 1-2 (748mg, 2mmol) was added dropwise to a mixture of compound 1-1 (1.5g, 4mmol) and tetrakistriphenylphosphinepalladium (20mg, 5%) In the toluene solution, after heating for two hours, compound 1-3 (972 mg, 2 mmol) was added dropwise, and refluxed overnight. After cooling, it was extracted with dichloromethane, spin-dried and purified with a silica gel column to obtain an asymmetric intermediate—compound 1-4 (1.7 g, 87%).

[0054] Synthesis of compound 1-5: under argon protection, (4-hexyl)phenylmagnesium bromide was added to compound 1-4 (1.5g, 3mmol) in tetrahydrofuran (30mL) to make the concentration 1mmol / mL , the mixed solution was heated to reflux for 16 hours, cooled to room temperature, extracted and spin-dried, directly added n-oc...

Embodiment 2

[0056] Example 2: Preparation of asymmetric ladder-shaped conjugated compound—compound 2-5 and its asymmetric A-D-A type conjugated small molecule—compound 2:

[0057]

[0058] Compound 2-5 and compound 2 use the same synthetic method as compound 1-5 and compound 1 in Example 1, the difference is that compound 1-2 and compound 1-7 are replaced by compound 2-2 and compound 2- 7. Elemental analysis of compound 2-5 Theoretical value: C, 78.16; H, 6.93; S, 14.90; Found value: C, 78.20; H, 6.88; S, 14.58. Compound 2 Elemental analysis Theoretical value: C, 77.84; H, 5.73; N, 3.71; Found value: C, 77.40; H, 5.45; N, 3.58.

Embodiment 3

[0059] Example 3: Preparation of asymmetric ladder-shaped conjugated compound—compound 5-5 and its asymmetric A-D-A type conjugated small molecule—compound 5:

[0060]

[0061] Compound 5-5 and compound 5 use the same synthetic method as compound 1-5 and compound 1 in Example 1, the difference is that compound 1-1, compound 1-2 and compound 1-3 are replaced by 5-1 , compound 5-2 and compound 5-3. Theoretical value of elemental analysis of compound 5-5: C, 77.10; H, 7.57; S, 15.33; found value: C, 77.20; H, 7.43; S, 15.01. Theoretical value of elemental analysis of compound 5: C, 74.10; H, 6.22; N, 2.93; found value: C, 74.40; H, 6.23; N, 3.01.

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Abstract

The invention discloses an asymmetric A-D-A type conjugated small molecule and its intermediate and application, using an asymmetric ladder-shaped conjugated compound as an electron donor, derivatization of indanedione and thienocyclopentanedione As electron acceptors, asymmetric A‑D‑A conjugated small molecules were synthesized. Such molecules have good solubility and thermal stability, and are suitable for large-area and low-cost solution processing and inkjet printing processing methods. The asymmetric A-D-D type conjugated small molecule in the present invention has higher molar extinction coefficient and very broad absorption spectrum, larger electron mobility and suitable lowest unoccupied orbital energy level and highest occupied orbital energy level, and the asymmetric intermediate core can strengthen the interaction between molecules, and can be used as an electron acceptor in non-fullerene organic polymer solar cells. Solar cells based on such small molecules can achieve higher voltage, current, fill factor, and photoelectric conversion efficiency.

Description

technical field [0001] The invention belongs to the field of organic photoelectric materials, and relates to an asymmetric A-D-A type conjugated small molecule and its application in organic photovoltaics. Background technique [0002] Energy crisis and environmental pollution are two global problems, and finding clean and renewable energy is the key to solving the problem. Solar radiation contains huge energy, which is inexhaustible and inexhaustible. Using solar energy to generate electricity is an effective method. The device that converts light energy into electricity is called a solar cell. At present, inorganic solar cells based on monocrystalline silicon have been used in production, and they have the advantages of high photoelectric conversion efficiency and long service life, but their manufacturing process is complex, expensive and cannot be mass-produced. Compared with inorganic solar cells, organic solar cells can be processed by solution (such as spin coating ...

Claims

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Application Information

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Patent Type & AuthorityPatents(China)
IPC IPC(8): C07D495/22H01L51/46
CPCC07D495/22H10K85/6576Y02E10/549
Inventor杨楚罗高威谢东君罗正辉
OwnerWUHAN UNIV