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Photoelectric conversion device and sensor and electronic device

A technology for photoelectric conversion and photoelectric conversion layer, which is applied in the fields of electric solid-state devices, photovoltaic power generation, electrical components, etc., and can solve the problems of difficulty in accurately predicting the properties of organic materials, and difficulty in easily controlling the properties of photoelectric conversion devices.

Pending Publication Date: 2021-05-11
SAMSUNG ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It can be difficult to precisely predict the properties of organic materials, which can make it difficult to easily control the properties required for photoelectric conversion devices

Method used

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  • Photoelectric conversion device and sensor and electronic device
  • Photoelectric conversion device and sensor and electronic device
  • Photoelectric conversion device and sensor and electronic device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0370] Synthesis Example 1: Synthesis of Compound 1-1

[0371] [Compound 1-1]

[0372]

[0373] [Reaction Scheme 1]

[0374]

[0375] 10.06g (25.1mmol) of 2,6-dibromo-9-phenyl-9H-carbazole, 18.52g (50.1mmol) of 9-phenyl-3-(4,4,5,5-tetramethyl Base-1,3,2-dioxaborolan-2-yl)-9H-carbazole and 3 mol% tetrakis(triphenylphosphine)palladium(0)(Pd(PPh 3 ) 4 ) was dissolved in 50ml of toluene solvent, and added thereto by adding 13.86g (100.3mmol) of K 2 CO 3 A solution prepared by dissolving in 25 ml of water was then heated and refluxed at 100°C for 12 hours. After removing the solvent from the organic layer, the product therefrom was separated and purified by silica gel column chromatography to obtain 13.5 g (74% yield) of 9,9',9"-triphenyl-9H,9' H,9"H-3,2':6',3"-triple carbazole (compound 1-1). The molecular weight of compound 1-1 is 725.90 g / mol.

[0376] 1 H-NMR (300MHz, dichloromethane-d2): δ8.49(s, 2H), 8.41(s, 1H), 8.31(d, 1H), 8.26(d, 1H), 8.21(d, 1H), 7.80 (t, ...

Embodiment 2

[0377] Synthesis Example 2: Synthesis of Compound 1-2

[0378] [Compound 1-2]

[0379]

[0380] [Reaction Scheme 2]

[0381]

[0382] 10.00 g (24.9 mmol) of 3,6-dibromo-9-phenyl-9H-carbazole, 15.04 g (52.4 mmol) of (9-phenyl-9H-carbazol-2-yl) boronic acid, and 3 mol% Pd(PPh 3 ) 4 Dissolve in the toluene solvent of 50ml, and add to it by the K of 13.78g (99.7mmol) 2 CO 3 A solution prepared by dissolving in 25 ml of water was then heated and refluxed at 100°C for 12 hours. After removing the solvent from the organic layer, the product therefrom was separated and purified by silica gel column chromatography to obtain 13.5 g (76% yield) of 9,9',9"-triphenyl-9H,9' H,9"H-2,3':6',2"-triple carbazole (compound 1-2). The molecular weight of compound 1-2 is 725.90 g / mol.

[0383] 1 H-NMR (500MHz, dichloromethane-d2): δ8.55(s, 2H), 8.48(s, 2H), 8.24(d, 2H), 7.80-7.78(m, 4H), 7.66-7.61(m , 12H), 7.54-7.41 (m, 11H), 7.30 (t, 2H).

Embodiment 3

[0384] Synthesis Example 3: Synthesis of Compound 80-1

[0385] [Compound 80-1]

[0386]

[0387] [Reaction scheme 3]

[0388]

[0389] (1) Synthesis of compound I-80-1

[0390] 10.04g (31.2mmol) of 3-bromo-6-phenyl-9H-carbazole, 9.84g (34.3mmol) of (9-phenyl-9H-carbazol-3-yl) boronic acid and 3 mol % Pd(PPh 3 ) 4 Dissolve in the toluene solvent of 50ml, and add to it by the K of 8.61g (62.3mmol) 2 CO 3 A solution prepared by dissolving in 25 ml of water was then heated and refluxed at 100°C for 12 hours. After removing the solvent from the organic layer, the product therefrom was separated and purified by silica gel column chromatography to obtain 11.2 g (74% yield) of 6,9'-diphenyl-9H,9'H-3 , 3'-bicarbazole (compound 1-80-1).

[0391] (2) Synthesis of compound 80-1

[0392] 11.20g (23.1mmol) of compound I-80-1 and 8.19g (25.4mmol) of 2-bromo-9-phenyl-9H-carbazole in 100ml of anhydrous toluene in 10 mol% bis(di benzylideneacetone)palladium(0)(Pd(dba) 2 ), 20 ...

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Abstract

Disclosed are a photoelectric conversion device and a sensor and an electronic device. The photoelectric conversion device includes a first electrode and a second electrode, a photoelectric conversion layer between the first electrode and the second electrode, the photoelectric conversion layer including a p-type semiconductor and an n-type semiconductor, and an organic buffer layer between the first electrode and the photoelectric conversion layer, the organic buffer layer including an organic buffer material, wherein a difference between a LUMO energy level of the organic buffer material and a LUMO energy level of the n-type semiconductor is greater than or equal to about 1.2 eV and the organic buffer material includes at least three carbazole moieties, and a sensor, and an electronic device including the same.

Description

[0001] Cross References to Related Applications [0002] This application claims priority and benefit from Korean Patent Application No. 10-2019-0141158 filed with the Korean Intellectual Property Office on November 6, 2019, the entire contents of which are incorporated herein by reference. technical field [0003] Photoelectric conversion devices, sensors and electronic devices are disclosed. Background technique [0004] Photoelectric conversion devices convert light into electrical signals using the photoelectric effect. Photoelectric conversion devices include photodiodes, phototransistors, and the like, and they can be applied to sensors or photodetectors. [0005] Sensors are increasingly requiring higher resolution, resulting in smaller pixel sizes. Currently, silicon photodiodes are widely used, but they may have degraded sensitivity because silicon photodiodes have a smaller absorption area due to the small pixels. Therefore, organic materials capable of replacin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/44H01L51/46H01L27/30
CPCH10K39/32H10K85/6572H10K30/353H10K30/82C07D209/86Y02E10/549H10K2101/30H10K30/30
Inventor 洪慧林崔泰溱许哲准朴敬培林宣晶
Owner SAMSUNG ELECTRONICS CO LTD