Preparation of highly transparent poly(meth)acrylates with enhanced refractive indices by radical (co)polymerization of seleno(meth)acrylates

Tokushita, Yoshihisa; Furuya, Shogo; Nobe, Shotaro; Nakabayashi, Kazuhiro; Samitsu, Sadaki; Mori, Hideharu

doi:10.1016/j.polymer.2021.124346

Cited by 3 publications

(3 citation statements)

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“…For instance, new classes of sulfur-containing products have been produced using inverse-vulcanization with elemental sulfur, [5,6] ring-opening polymerization with carbonyl sulfide, [7] and thiol-ene [8][9][10][11][12][13] and thiol-yne [14,15] reactions. Various synthetic methodologies that produce high refractive index polymers and hybrids also rely on the incorporation of phosphorus units, [16] highly polarizable atoms (Si, Ge, Sn), [17] zinc, [18] zirconium, [19] and selenium units, [9,[20][21][22] and employments of charge-transfer complexation [23] and hydrogen bonds. [24] In addition, heteroaromatic rings are attractive building blocks for high-refractiveindex polymers because ─C═N─C─ bonds exhibit higher molar refraction (4.10) than ─C═C─C─ bonds (1.73).…”

Section: Introductionmentioning

confidence: 99%

High Refractive Index Copolymers from Aromatic Heterocycle‐Based Vinyl Sulfides and Phthalimide/Maleimide Derivatives

Watanabe,

Morikawa,

Samitsu

et al. 2023

Macro Chemistry & Physics

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Herein, we present the rational design and facile synthesis of high‐refractive‐index copolymers with good optical transparency and tunable thermal stability using aromatic heterocycle‐based vinyl sulfides via conventional radical copolymerization. 2‐Thiazolylvinylsulfide (2TVS), 1,3,4‐thiadiazolylvinylsulfide (1,3,4‐TVS), 3‐methylimidazolylvinylsulfide (3MIVS), and 5‐methlthio‐1,3,4‐thiadiazolylvinylsulfide (MeSTVS) were selected to enhance the refractive index, and N‐vinylphthalimide (NVPI) and N‐phenylmaleimide (NPMI) were chosen as comonomers to achieve improved transparency and thermal stability while maintaining the refractive index. The sulfur, ‐C = N‐, and imide contents in the copolymers were varied by adjusting the monomer structures and their compositions, and their effects on the refractive index, Abbe number, and optical and thermal properties were investigated. The MeTVS monomer in poly(MeSTVS) and poly(MeSTVS‐co‐NVPI) contained three sulfur atoms and two ‐C = N‐ units; consequently, these polymers exhibited excellent refractive indices in the 1.7139–1.6567 range at 589 nm, Abbe numbers between 19.1–29.1, good transparency (>90% at 400 nm), and tunable thermal properties (Tg = 49–138 °C, Td10 = 244–268 °C). Optically transparent poly(1,3,4‐TVS‐co‐NVPI) films (> 95% at 400 nm) with improved thermal stability (Tg = 89–175 °C, Td10 = 251–301 °C) were obtained, while maintaining a relatively high refractive index (1.6662–1.6752).This article is protected by copyright. All rights reserved

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Section: Introductionmentioning

confidence: 99%

High Refractive Index Copolymers from Aromatic Heterocycle‐Based Vinyl Sulfides and Phthalimide/Maleimide Derivatives

Watanabe,

Morikawa,

Samitsu

et al. 2023

Macro Chemistry & Physics

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“…Optical polymers have long been used in integrated photonics, [1,2] as this class of materials offers wide tunability of both optical and thermomechanical properties via compositional variations, while retaining low absorption loss at telecom wavelengths. [3][4][5][6][7][8] Furthermore, polymeric materials are relatively inexpensive to synthesize and are amenable to a wider range of efforts have been made to prepare optical polymers with high RI for use in consumer optics (n ≈ 1.6-1.7) or holography [18][19][20][21][22][23][24][25] however the development of high RI polymers for integrated photonics remains an important technological target. Optical ring resonators have been fabricated from commercially available photopolymers, such as SU8 (n = 1.57), however, polymerbased ring resonators with both reduced dimensions and high Q-factor resonances have not been achieved.…”

Section: Introductionmentioning

confidence: 99%

“…[ 14–17 ] However, fabrication processes for these materials remain non‐trivial, requiring multi‐step high temperature methods, or the use of unconventional toxic solvents which has limited wide‐scale deployment. Numerous efforts have been made to prepare optical polymers with high RI for use in consumer optics ( n ≈ 1.6–1.7) or holography [ 18–25 ] however the development of high RI polymers for integrated photonics remains an important technological target. Optical ring resonators have been fabricated from commercially available photopolymers, such as SU8 ( n = 1.57), however, polymer‐based ring resonators with both reduced dimensions and high Q‐factor resonances have not been achieved.…”

Section: Introductionmentioning

confidence: 99%

High Refractive Index Chalcogenide Hybrid Inorganic/Organic Polymers for Integrated Photonics

Nishant

Kim

Showghi

et al. 2022

Advanced Optical Materials

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fabrication techniques for device fabrication in contrast to inorganic counterpart materials, such as silicon (Si) and silicon nitride (SiN). As a result, optical polymers are increasingly seen as cost-effective solutions for manufacturing photonic devices in high volume. Despite these numerous processing advantages, optical polymer materials for integrated photonics remain limited relative to inorganic materials with respect to critical optical properties, especially refractive index (n, or RI). The vast majority of current optical polymers have a refractive index ranging between 1.3-1.6 at telecom wavelengths, which is significantly lower than the RI values of SiN, lithium niobate (n ≈ 2.0-2.2), or higher RI materials such as Si, [9,10] indium phosphide, or germanium (n ≈ 3.5-4.0). Because of these dramatically lower RI values, on-chip integrated photonic components, such as waveguides or ring resonators fabricated using optical polymers require much larger feature sizes beyond what is tenable for numerous on-chip device systems and preclude the fabrication of curved features with tight bend radii which are essential integrated optical elements. With an ever-increasing demand for high density integrated optical circuitry, the large areal footprint of state-of-the-art polymer devices due to limited RI contrast remains a critical limitation toward realizing all-polymer photonic circuits for high density interconnects and integration. Hence, there is a compelling technological need for high RI polymers (n >> 1.6 at telecom at 1310 and 1550 nm) that are amenable to thin film processing and high throughput nano/ microfabrication techniques (e.g., photolithography). There are a handful of inorganic materials, such as Hydex glass [11,12] and silicon oxynitride (SiON), [13] which have been studied to create inexpensive, earth-abundant inorganic materials that achieve RI values ranging from n = 1.6-2.0 at telecom wavelengths. Furthermore, recent work on solution-processable chalcogenide glasses (ChGs) has been explored to create thin films and integrated photonic components, such as single-mode waveguides in the mid-wave infrared (MWIR), which exploit the high RI and high transparency ChGs. [14][15][16][17] However, fabrication processes for these materials remain non-trivial, requiring multi-step high temperature methods, or the use of unconventional toxic solvents which has limited wide-scale deployment. Numerous Optical polymer-based integrated photonic devices are gaining interest for applications in optical packaging, biosensing, and augmented/virtual reality (AR/VR). The low refractive index of conventional organic polymers has been a barrier to realizing dense, low footprint photonic devices. The fabrication and characterization of integrated photonic devices using a new class of high refractive index polymers, chalcogenide hybrid inorganic/organic polymers (CHIPs), which possess high refractive indices and lower optical losses compared to traditional hydrocarbon-based polymers, are reported. These optical polyme...

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Synthesis and characterization of aromatic poly(phosphonate)s, poly(thiophosphonate)s, and poly(selenophosphonate)s for high refractive index

et al. 2023

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Preparation of highly transparent poly(meth)acrylates with enhanced refractive indices by radical (co)polymerization of seleno(meth)acrylates

Cited by 3 publications

References 58 publications

High Refractive Index Copolymers from Aromatic Heterocycle‐Based Vinyl Sulfides and Phthalimide/Maleimide Derivatives

High Refractive Index Copolymers from Aromatic Heterocycle‐Based Vinyl Sulfides and Phthalimide/Maleimide Derivatives

High Refractive Index Chalcogenide Hybrid Inorganic/Organic Polymers for Integrated Photonics

Synthesis and characterization of aromatic poly(phosphonate)s, poly(thiophosphonate)s, and poly(selenophosphonate)s for high refractive index

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