Synthesis and Characterization of Benzobisoxazole-based Conjugated Polymers for Organic Photodetectors

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DOI: https://doi.org/10.30564/opmr.v5i2.6192

Abstract:

Benzo[1,2-d:4,5-d’]bis(oxazole) (BBO) is a conjugated building block that can be easily synthesized for the development of organic optoelectronic polymers. Here, the authors synthesized BBO-based polymers, P1 and P2, by coupling BBO with thiophenes for use in organic photodetectors (OPDs). The optical characteristics of P1 and P2 make them suitable for OPDs, as they selectively absorb the green light with a narrow bandwidth in the range of 500–600 nm. The OPD devices were fabricated by making a bulk heterojunction active layer between the synthesized polymers and a nonfullerene acceptor, IDIC. P1-based devices showed slightly higher responsivity (R) of 0.169 A/W than 0.112 A/W of P2-based devices. However, the P2-based device was higher than D* value of the P1-based under 100 μW/cm², which was due to the influence of excessive thiophene units that had low dark current density.

References:

[1] Chow, P.C., Someya, T., 2020. Organic photodetectors for next-generation wearable electronics. Advanced Materials. 32(15), 1902045. DOI: https://doi.org/10.1002/adma.201902045 [2] Liu, J., Gao, M., Kim, J., et al., 2021. Challenges and recent advances in photodiodes-based organic photodetectors. Materials Today. 51, 475–503. DOI: https://doi.org/10.1016/j.mattod.2021.08.004 [3] Xia, K., Li, Y., Wang, Y., et al., 2020. Narrowband‐absorption‐type organic photodetectors for the far‐red range based on fullerene‐free bulk heterojunctions. Advanced Optical Materials. 8(8), 1902056. DOI: https://doi.org/10.1002/adom.201902056 [4] Sabah, F.A., 2021. Organic polymer materials for light emitting diode applications. Organic Polymer Material Research. 3(2), 24–25. DOI: https://doi.org/10.30564/opmr.v3i2.4348 [5] Chakraborty, S., Chatterjee, R., Bandyopadhyay, A., 2022. A brief review on fundamentals of conductive polymer (CPs). Organic Polymer Material Research. 4(1), 1–11. DOI: https://doi.org/10.30564/opmr.v4i1.4395 [6] Luo, Y., 2023. Powering the future: Hydrogel-based soft ionic conductors energize flexible and wearable triboelectric nanogenerators. Organic Polymer Material Research. 5(1), 12–14. DOI: https://doi.org/10.30564/opmr.v5i1.5818 [7] Wei, Y., Chen, H., Liu, T., et al., 2021. Self-powered organic photodetectors with high detectivity for near infrared light detection enabled by dark current reduction. Advanced Functional Materials. 31(52), 2106326. DOI: https://doi.org/10.1002/adfm.202106326 [8] Kim, J., Kang, J., Jung, I.H., 2022. Synthesis and characterization of a copper (II) phthalocyanine-based dye for organic photodetectors. Bulletin of the Korean Chemical Society. 43(9), 1130–1135. DOI: https://doi.org/10.1002/bkcs.12595 [9] Kang, J., Kim, J., Won, J.H., et al., 2021. Enhanced static and dynamic properties of highly miscible fullerene-free green-selective organic photodetectors. ACS Applied Materials & Interfaces. 13(21), 25164–25174. DOI: https://doi.org/10.1021/acsami.1c02357 [10] Jeong, W., Kang, J., Lim, S.Y., et al., 2022. Spontaneously induced hierarchical structure by surface energy in novel conjugated polymer-based ultrafast-response organic photodetectors. Advanced Optical Materials. 10(9), 2102607. DOI: https://doi.org/10.1002/adom.202102607 [11] Jeong, W., Kang, J., Lee, D., et al., 2023. Development of high-performance organic photodetectors by understanding origin of dark current density with synthesis of photoconductive polymers. Chemical Engineering Journal. 473, 145178. DOI: https://doi.org/10.1016/j.cej.2023.145178 [12] Jeong, W., Kang, J., Jeong, M.K., et al., 2021. Development of low bandgap polymers for red and near-infrared fullerene-free organic photodetectors. New Journal of Chemistry. 45(24), 10872–10879. DOI: https://doi.org/10.1039/d1nj01694f [13] Kim, H., Kang, J., Park, J., et al., 2022. All-polymer photodetectors with n-Type polymers having nonconjugated spacers for dark current density reduction. Macromolecules. 55(21), 9489–9501. DOI: https://doi.org/10.1021/acs.macromol.2c01769 [14] Kim, H., Kang, J., Kim, M.I., et al., 2023. Development of n-type small-molecule acceptors for low dark current density and fast response organic photodetectors. ACS Applied Materials & Interfaces. 15(49), 57545–57555. DOI: https://doi.org/10.1021/acsami.3c11174 [15] Liu, Y., Wan, X., Wang, F., et al., 2011. Spin-coated small molecules for high performance solar cells. Advanced Energy Materials. 1(5), 771–775. DOI: https://doi.org/10.1002/aenm.201100230 [16] Fan, Q., Su, W., Guo, X., et al., 2016. A new polythiophene derivative for high efficiency polymer solar cells with PCE over 9%. Advanced Energy Materials. 6(14), 1600430. DOI: https://doi.org/10.1002/aenm.201600430 [17] Tlach, B.C., Tomlinson, A.L., Bhuwalka, A., et al., 2011. Tuning the optical and electronic properties of 4,8-disubstituted benzobisoxazoles via alkyne substitution. The Journal of Organic Chemistry. 76(21), 8670–8681. DOI: https://doi.org/10.1021/jo201078w [18] Zahran, M.K., Faheem, T.S., Abdel-Karim, A.M., et al., 2021. Enhanced optical as well as electrical properties of poly 2-acetyl pyrrole P (2-APy) for optoelectric applications. Chemical Papers. 75, 3599–3606. DOI: https://doi.org/10.1007/s11696-021-01609-8 [19] Luponosov, Y.N., Solodukhin, A.N., Mannanov, A.L., et al., 2021. Effect of oligothiophene π-bridge length in D-π-A star-shaped small molecules on properties and photovoltaic performance in single-component and bulk heterojunction organic solar cells and photodetectors. Materials Today Energy. 22, 100863. DOI: https://doi.org/10.1016/j.mtener.2021.100863 [20] Zhang, S., Ocheje, M.U., Huang, L., et al., 2019. The critical role of electron-donating thiophene groups on the mechanical and thermal properties of donor–acceptor semiconducting polymers. Advanced Electronic Materials. 5(5), 1800899. DOI: https://doi.org/10.1002/aelm.201800899 [21] Lv, L., Yu, J., Sui, X., et al., 2019. Significant enhancement of responsivity of organic photodetectors upon molecular engineering. Journal of Materials Chemistry C. 7(19), 5739–5747. DOI: https://doi.org/10.1039/c9tc00576e [22] Yang, D., Ma, D., 2019. Development of organic semiconductor photodetectors: From mechanism to applications. Advanced Optical Materials. 7(1), 1800522. DOI: https://doi.org/10.1002/adom.201800522