Enhanced Optical and Thermal Stability of Blue Pyrrole Derivatives for Color Filter in Image Sensors

We designed and synthesized two novel blue pyrrole derivatives, 2-(3-cyano-4-(4-(dibutylamino)phenyl)-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)malononitrile (BAPCP) and 2-(3-cyano-4-(4-(dihexylamino)phenyl)-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)malononitrile (HAPCP), as potential candidates for use in...

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Main Authors: Sunwoo Park, Sangwook Park, Saeyoung Oh, Hyukmin Kwon, Hayoon Lee, Kiho Lee, Chun Yoon, Jongwook Park
Format: Article
Language:English
Published: MDPI AG 2025-01-01
Series:Applied Sciences
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Online Access:https://www.mdpi.com/2076-3417/15/2/799
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author Sunwoo Park
Sangwook Park
Saeyoung Oh
Hyukmin Kwon
Hayoon Lee
Kiho Lee
Chun Yoon
Jongwook Park
author_facet Sunwoo Park
Sangwook Park
Saeyoung Oh
Hyukmin Kwon
Hayoon Lee
Kiho Lee
Chun Yoon
Jongwook Park
author_sort Sunwoo Park
collection DOAJ
description We designed and synthesized two novel blue pyrrole derivatives, 2-(3-cyano-4-(4-(dibutylamino)phenyl)-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)malononitrile (BAPCP) and 2-(3-cyano-4-(4-(dihexylamino)phenyl)-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)malononitrile (HAPCP), as potential candidates for use in image sensor color filters. The properties of these new compounds were evaluated, focusing on their optical and thermal characteristics in solution and color filter film forms. The molar extinction coefficient values of BAPCP and HAPCP in solution were 6.03 × 10<sup>4</sup> and 6.91 × 10<sup>4</sup> L/mol·cm. The molar extinction coefficient of HAPCP was 4.5 times higher than that of the commercially used Disperse Blue 359. The synthesized compounds exhibited transmittance values that meet commercial requirements, with 88.6% at 450 nm and 0.73% at 530 nm. Both newly synthesized compounds met the decomposition temperature requirement of over 230 °C, which is necessary for the manufacturing process of image sensor color filters. The decomposition temperatures of both compounds were approximately 19 °C higher than that of Disperse Blue 359. When the thermal stability of color filter films for image sensors was evaluated, BAPCP demonstrated excellent optical properties before and after thermal stability testing, maintaining its characteristics in an optimized molecular form. Accordingly, BAPCP appears to have favorable potential as a blue colorant for image sensors, attributed to its superior optical and thermal stability characteristics.
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spelling doaj-art-32943d5b887f4b0096b20b43c5d9afa62025-01-24T13:20:52ZengMDPI AGApplied Sciences2076-34172025-01-0115279910.3390/app15020799Enhanced Optical and Thermal Stability of Blue Pyrrole Derivatives for Color Filter in Image SensorsSunwoo Park0Sangwook Park1Saeyoung Oh2Hyukmin Kwon3Hayoon Lee4Kiho Lee5Chun Yoon6Jongwook Park7Integrated Engineering, Department of Chemical Engineering, Kyung Hee University, Gyeonggi 17104, Republic of KoreaIntegrated Engineering, Department of Chemical Engineering, Kyung Hee University, Gyeonggi 17104, Republic of KoreaIntegrated Engineering, Department of Chemical Engineering, Kyung Hee University, Gyeonggi 17104, Republic of KoreaIntegrated Engineering, Department of Chemical Engineering, Kyung Hee University, Gyeonggi 17104, Republic of KoreaIntegrated Engineering, Department of Chemical Engineering, Kyung Hee University, Gyeonggi 17104, Republic of KoreaIntegrated Engineering, Department of Chemical Engineering, Kyung Hee University, Gyeonggi 17104, Republic of KoreaDepartment of Chemistry, Sejong University, 98 Gunja-dong, Gwangjin-gu, Seoul 05006, Republic of KoreaIntegrated Engineering, Department of Chemical Engineering, Kyung Hee University, Gyeonggi 17104, Republic of KoreaWe designed and synthesized two novel blue pyrrole derivatives, 2-(3-cyano-4-(4-(dibutylamino)phenyl)-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)malononitrile (BAPCP) and 2-(3-cyano-4-(4-(dihexylamino)phenyl)-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)malononitrile (HAPCP), as potential candidates for use in image sensor color filters. The properties of these new compounds were evaluated, focusing on their optical and thermal characteristics in solution and color filter film forms. The molar extinction coefficient values of BAPCP and HAPCP in solution were 6.03 × 10<sup>4</sup> and 6.91 × 10<sup>4</sup> L/mol·cm. The molar extinction coefficient of HAPCP was 4.5 times higher than that of the commercially used Disperse Blue 359. The synthesized compounds exhibited transmittance values that meet commercial requirements, with 88.6% at 450 nm and 0.73% at 530 nm. Both newly synthesized compounds met the decomposition temperature requirement of over 230 °C, which is necessary for the manufacturing process of image sensor color filters. The decomposition temperatures of both compounds were approximately 19 °C higher than that of Disperse Blue 359. When the thermal stability of color filter films for image sensors was evaluated, BAPCP demonstrated excellent optical properties before and after thermal stability testing, maintaining its characteristics in an optimized molecular form. Accordingly, BAPCP appears to have favorable potential as a blue colorant for image sensors, attributed to its superior optical and thermal stability characteristics.https://www.mdpi.com/2076-3417/15/2/799pyrrole derivativesblue colorantcolor filterimage sensor
spellingShingle Sunwoo Park
Sangwook Park
Saeyoung Oh
Hyukmin Kwon
Hayoon Lee
Kiho Lee
Chun Yoon
Jongwook Park
Enhanced Optical and Thermal Stability of Blue Pyrrole Derivatives for Color Filter in Image Sensors
Applied Sciences
pyrrole derivatives
blue colorant
color filter
image sensor
title Enhanced Optical and Thermal Stability of Blue Pyrrole Derivatives for Color Filter in Image Sensors
title_full Enhanced Optical and Thermal Stability of Blue Pyrrole Derivatives for Color Filter in Image Sensors
title_fullStr Enhanced Optical and Thermal Stability of Blue Pyrrole Derivatives for Color Filter in Image Sensors
title_full_unstemmed Enhanced Optical and Thermal Stability of Blue Pyrrole Derivatives for Color Filter in Image Sensors
title_short Enhanced Optical and Thermal Stability of Blue Pyrrole Derivatives for Color Filter in Image Sensors
title_sort enhanced optical and thermal stability of blue pyrrole derivatives for color filter in image sensors
topic pyrrole derivatives
blue colorant
color filter
image sensor
url https://www.mdpi.com/2076-3417/15/2/799
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AT saeyoungoh enhancedopticalandthermalstabilityofbluepyrrolederivativesforcolorfilterinimagesensors
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