Synthesis and characterization of thianthrene-containing preimidized soluble polyimide resins and the derived films with high refractive indices and good optical transparency

Zhang, Yan; Liu, Jingang; Wu, Xiaowen; Bi, Hong-sheng; Jiang, Ganglan; Zhi, Xin‐xin; Lin, Qi; Zhang, Xiumin

doi:10.1007/s10965-018-1664-6

Cited by 12 publications

(9 citation statements)

References 37 publications

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“…In a three-necked round-bottom flask set up with a Dean−Stark trap fitted with a condenser, 2.56 g (0.0045 mol) of 1,3,5-tris(4-fluoro-3-trifluoromethylphenyl)benzene, 2.134 g (0.017 mol) of 4-aminobenzenethiol, 3.015 g (0.022 mol) of K 2 CO 3 , 25 mL of NMP, and 40 mL of toluene were added under a constant nitrogen flow. Similar to the preparation of the diamino compound, this 13 C NMR (CDCl 3 ): δ 147.9 (13), 141.1 (2), 140.1 (6), 137.3 (11), 137.2 (3), 130.3 (8), 129.4 (7), 127.4 (q, 2 J CF = 31.0 Hz; 5), 125.2 (q, 3 J CF = 5.6 Hz; 4), 124.8 (1), 123.9 (q, 1 J CF = 275 Hz; 9), 118.2 (10), 116.1 ppm (12). 19 F NMR (CDCl 3 ): δ −62.5 ppm.…”

Section: 35-tris(4-((2-(trifluoromethyl)phenyl)thio)aniline)benzene (...mentioning

confidence: 95%

“…After removal of water, the reaction temperature was increased to 150 °C and maintained for another 4 h. Then, after cooling of the temperature of the reaction to room temperature, the reaction mixture was poured into 1 L of doubly distilled water to obtain a solid compound that was yellowish in color. This crude product was then purified by recrystallization in acetone (Scheme 1 13 C NMR (CDCl 3 ): δ 147.9 (13), 142.1 (2), 139.5 (6), 137.2 (11), 130.8 (3), 129.4 (7), 128.5 (8), 127.4 (q, 2 J CF = 31.0 Hz; 5), 124.6 (1), 123.8 (q, 1 J CF = 275 Hz; 9), 123.4 (q, 3 J CF = 5.7 Hz; 4), 118.2 (10), 116.0 ppm (12). 19 F NMR (CDCl 3 ): δ −62.7 ppm.…”

Section: Synthesis Of Monomers and Polymers 241 44′-((thiophene-25-di...mentioning

confidence: 99%

“…Polymer 13 C NMR (CDCl 3 ): δ 166.5 and 166.4 (14,15), 164.0 (18), 152.7 (22), 147.6 (25), 142.3 (2), 134.6 (6), 134.2 (7), 134.1 (16), 134.0 (13), 132.9 (3), 132.7 (12), 131.6 (10), 130.8 (q, 2 J CF = 30.7 Hz; 5), 128.9 (8), 128.8 (24), 127.2 (11), 125.9 (20), 125.4 (1), 124.9 (21), 123.8 (q; 4), 123.4 (q, 1 J CF = 274 Hz; 9), 123.2 (19), 120.0 (23), 111.9 (17), 42.6 (26), 31.0 ppm (27). 19 16), 131.2 (q, 2 J CF = 30.5 Hz; 5), 130.9 (10), 129.0 (8), 127.1 (11), 125.5 (1), 125.4 (17), 124.2 (20), 123.8 (q; 4), 123.4 (q, 1 J CF = 275 Hz; 9), 123.3 (q, 1 J CF = 288 Hz; 23), 65.3 ppm (sept, 2 J CF =26 Hz; 22). 19 F NMR (CDCl 3 ): δ −62.1 (9), −64.4 ppm (23).…”

Section: Polymerization and Polymer Film Preparationsmentioning

confidence: 99%

“…1 H NMR (DMF-d 7 ): δ 8.21 (4), 8.13(20),8.05(8),7.91 (1),7.75(19), 7.72 (17), 7.66(11,12), 7.64(23,24), 7.58 ppm(7) 13. C NMR1 H NMR (DMF-d 7 ): δ 8.5−8.25 (reacted TAm), 8.21 (4), 8.13 (20), 8.05 (8), 7.91 (1), 7.8−7.5 ppm (7, 11, 12, 17, 19, reacted 127.4 (1), 126.4 (20), 125.4 (19), 123.9 (4), 114.1 ppm (17).…”

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Sulfur-Rich Polyimides Containing Bis(3-(trifluoromethyl)phenyl)thiophene for High-Refractive-Index Applications

et al. 2022

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Three series of sulfur-containing polyimides with the bis(3-(trifluoromethyl)phenyl)thiophene moiety were reported. The synthesis of high-refractive-index polyimides was carried out using a nucleophilic substitution reaction. For that, two new sulfur-containing aromatic amino monomers were developed, one bifunctional and one trifunctional. The monomer and polymer structures were successfully characterized by NMR and Fourier transform infrared (FTIR) spectroscopic methods. Free-standing polyimide films of ∼10 μm were prepared, and they were found to have high thermodynamic stability with T g as high as 257 °C and T d5% above 500 °C. The films were flexible as well as tough with up to 16 ± 7% elongation at break, with a Young’s modulus of 2.6 ± 5 GPa. Indication for melt processability of one of the polyimides was also demonstrated at a temperature of 30 °C above its T g. Thin films with thickness in the nanometer range were coated over modified Si-wafers. Increase in the sulfur and aromatic contents in the polymer backbone resulted in the increase of their refractive index; thus, the polymers synthesized in this work exhibited refractive index as high as 1.76 at 589 nm. The transmittance and birefringence of the polyimides were found to improve by modification in the chemical structure. The tuneable optical properties and good dynamic stability of the polyimides make them potential candidates in optoelectronic applications.

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Section: 35-tris(4-((2-(trifluoromethyl)phenyl)thio)aniline)benzene (...mentioning

confidence: 95%

Section: Synthesis Of Monomers and Polymers 241 44′-((thiophene-25-di...mentioning

confidence: 99%

Section: Polymerization and Polymer Film Preparationsmentioning

confidence: 99%

mentioning

confidence: 99%

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Sulfur-Rich Polyimides Containing Bis(3-(trifluoromethyl)phenyl)thiophene for High-Refractive-Index Applications

et al. 2022

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“…The liquid crystal cells fabricated with the organo-soluble PI alignment layer exhibited low curing temperature (<200°C), high VHR, and good alignment ability to liquid crystal molecules. In the current work, as one of continuous work developing high performance PI materials for optoelectronic applications [31][32][33][34], a series of imidized PIs were prepared from an ester-linked semi-alicyclic dianhydride and aromatic diamines. Compared with the PI alignment layers derived from substitutedtetralin dianhydrides in our previous work [34], the current PI systems are expected to provide better comprehensive properties for the derived PI alignment layers, including higher optical transparency, lower curing temperature, and higher degree of imidization at the TFT-LCD processing temperature (230°C).…”

mentioning

confidence: 99%

Synthesis and characterization of soluble ester-containing polyimide alignment layers with high voltage holding ratio features and potential applications in TFT-LCDs

Zhi¹,

Bi²,

Liu³

et al. 2019

Express Polym. Lett.

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Polyimide (PI) represents a class of high performance heteroaromatic polymers characterized by excellent thermal and environmental stability, high mechanical and dielectric properties as well as flexible molecular structure designability [1-3]. Various functionalities have been achieved for PIs via elaborate combination of specific dianhydride and diamine monomers so as to meet the property demands of high-tech applications [4-6]. Among the various functional PIs, semi-alicyclic PIs derived from alicyclic dianhydrides and aromatic diamines proved to possess the best combined properties considering the polymerization reactivity and the acidity/basicity of the starting monomers [7]. Thus, such kinds of semi-alicyclic PIs usually exhibited superior thermal and mechanical properties, and higher molecular weights to their analogous PIs derived from aromatic dianhydrides and alicyclic diamines or from both of alicyclic dianhydride and diamines [8]. Good comprehensive properties of semi-alicyclic PIs derived from alicyclic dianhydrides and aromatic diamines make them much attractive in optoelectronic fields in recent years [9-11]. The successful 923

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Synthetic strategies for highly transparent and colorless polyimide film

Liu

Wang

2022

J of Applied Polymer Sci

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Polyimide (PI) is one of the best engineering plastics with excellent thermal, mechanical, dielectric performance and chemical stability. Among various PI products, film is one of the most dominant types. If PI films are to be applied to optical devices and display equipment, it is necessary to improve their optical transparency in the ultraviolet–visible region. However, improving the optical transparency of PI films would affect their thermal performance including thermal and dimensional stability. Therefore, how to balance optical and thermal performance to obtain highly transparent PI films with the best overall performance becomes a focus of current research field. In this review, we categorize transparent PI films into highly transparent PI, transparent PI with high glass transition temperature (Tg) and transparent PI with low coefficient of thermal expansion (CTE) based on their optical and thermal properties. Then, we review research progress in the field of polymer molecular design including synthesis strategies and properties in recent 5 years, to inspire research ideas and elaborate on the possible ways to develop high‐performance, colorless and transparent PI materials.

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Synthesis and characterization of thianthrene-containing preimidized soluble polyimide resins and the derived films with high refractive indices and good optical transparency

Cited by 12 publications

References 37 publications

Sulfur-Rich Polyimides Containing Bis(3-(trifluoromethyl)phenyl)thiophene for High-Refractive-Index Applications

Sulfur-Rich Polyimides Containing Bis(3-(trifluoromethyl)phenyl)thiophene for High-Refractive-Index Applications

Synthesis and characterization of soluble ester-containing polyimide alignment layers with high voltage holding ratio features and potential applications in TFT-LCDs

Synthetic strategies for highly transparent and colorless polyimide film

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