Back
 MSA  Vol.11 No.5 , May 2020
Epoxy Methacrylate Resin as Binder Polymer for Black Negative-Tone Photoresists
Abstract: Epoxy acrylate (EA) resin, which originates from epoxides, has long been served as a photocurable coating and adhesive material owing to its double bonds. Specifically, alkaline-developable EA resins can be used as a binder polymer in negative-tone photoresists. In this work, we synthesized a series of acidic polyester-type epoxy methacrylate resins, characterized the intermediates and products, and tested their performance as a binder polymer for the photolithographic micro-patterning of the pixel-defining layer on organic light-emitting diodes in comparison to a widely used commercial binder polymer. Copolymer-type binder polymer BP-2-2 was produced excellent patterning with no residue due to its high compatibility with the black mill base.
Cite this paper: Shi, G. , Baek, K. , Ahn, S. , Bae, J. , Kim, J. and Park, L. (2020) Epoxy Methacrylate Resin as Binder Polymer for Black Negative-Tone Photoresists. Materials Sciences and Applications, 11, 285-295. doi: 10.4236/msa.2020.115019.
References

[1]   May, C.A. (1988) Epoxy Resins: Chemistry and Technology, Second Edition.

[2]   Chattopadhyay, D.K., Panda, S.S. and Raju, K.V.S.N. (2005) Thermal and Mechanical Properties of Epoxy Acrylate/Methacrylates UV Cured Coatings. Progress in Organic Coatings, 54, 10-19.
https://doi.org/10.1016/j.porgcoat.2004.12.007

[3]   Hong, B.T., Shin, K.S. and Kim, D.S. (2005) Ultraviolet-Curing Behavior of an Epoxy Acrylate Resin System. Journal of Applied Polymer Science, 98, 1180-1185.
https://doi.org/10.1002/app.22130

[4]   Park, Y.J., Lim, D.H., Kim, H.J., Park, D.S. and Sung, I.K. (2009) UV- and Thermal-Curing Behaviors of Dual-Curable Adhesives Based on Epoxy Acrylate Oligomers. International Journal of Adhesion and Adhesives, 29, 710-717.
https://doi.org/10.1016/j.ijadhadh.2009.02.001

[5]   Tsukada, K., Isobe, A., Hayashi, N., Abo, M. and Ogawa, K. (1976) Photosensitive Epoxy-Acrylate Resin Compositions. US Patent No. US3989610A.

[6]   Hosomi, T., Hayai, H. and Baba, T. (1998) Resin Composition and Printed Circuit Board Using the Same. US Patent No. US5726219A.

[7]   Shi, G., Kim, J., Baek K., Bae, J. and Park, L.S. (2019) Melt and One-Pot Solution Synthesis of Thermally Stable, Organosoluble and Photocurable Acidic Polyimides. Materials Sciences and Applications, 10, 687-696.
https://doi.org/10.4236/msa.2019.1011049

[8]   Kim, J., Park, K., Lee, D. and Bae, J.Y. (2011) Synthesis of Fluorene-Containing Photosensitive Polymer and Its Application to the Carbon Black-Based Photoresist for LCD Color-Filter. Polymer (Korea), 35, 87-93.
https://doi.org/10.7317/pk.2011.35.1.87

[9]   Shi, G., Park, S.H., Kim, J., Kim, M. and Park, L.S. (2018) Side-Chain Polyimides as Binder Polymers for Photolithographic Patterning of a Black Pixel Define Layer for Organic Light Emitting Diode. International Journal of Polymer Science, 2018, Article ID:3790834.
https://doi.org/10.1155/2018/3790834

[10]   Shi, G., Baek, K., Ahn, S.H., Bae, J., Kim, J. and Park, L.S. (2019) Synthesis of New Binder Polymers for Photolithographic Patterning of Black Pixel Define Layers of Organic Light Emitting Diode. Materials Sciences and Applications, 10, 687-696.
https://doi.org/10.4236/msa.2019.1011049

[11]   Kuo, K.H., Chiu, W.Y., Hsieh, K.H. and Don, T.M. (2009) Novel UV-Curable and Alkali-Soluble Resins for Light-Shielding Black Matrix Application. European Polymer Journal, 45, 474-484.
https://doi.org/10.1016/j.eurpolymj.2008.10.044

[12]   Diethelm, M., Penninck, L., Altazin, S., Hiestand, R., Kirsch, C. and Ruhstaller, B. (2018) Quantitative Analysis of Pixel Crosstalk in AMOLED Displays. Journal of Information Display, 19, 61-69.
https://doi.org/10.1080/15980316.2018.1428232

[13]   Kim, N. S., Lee, W.Y. and Suh, M.C. (2018) Suppression of the Color Shift of Microcavity Organic Light-Emitting Diodes Through the Introduction of a Circular Polarizer with a Nanoporous Polymer Film. Journal of Information Display, 19, 91-98.
https://doi.org/10.1080/15980316.2018.1454348

[14]   Kuo, K.H., Chiu, W.Y. and Don, T.M. (2009) Synthesis of UV-Curable/Alkali-Soluble Dispersants Used for Black Photoresist with a High Loading of Carbon Black. Journal of Applied Polymer Science, 115, 1803-1813.
https://doi.org/10.1002/app.31304

[15]   Dass, C. (2006) Fundamentals of Contemporary Mass Spectrometry.
https://doi.org/10.1002/0470118490

[16]   Park, H., Yoo, S., Ahn, H., Bang, J., Jeong, Y., Yi, M., Won, J.C., Jung, S. and Kim, Y.H. (2019) Low-Temperature Solution-Processed Soluble Polyimide Gate Dielectrics: From Molecular-Level Design to Electrically Stable and Flexible Organic Transistors. ACS Applied Materials & Interfaces, 11, 45949-45958.
https://doi.org/10.1021/acsami.9b14041

 
 
Top