Low‐temperature curable, alkaline‐developable, and negative‐type photosensitive polyimide with high resolution and mechanical properties based on chain extendable poly(amic acid) and photo‐base generator

Yeh, Yao Ming; Karapala, Vamsi Krishna; Ueda, Mitsuru; Hsu, Chain‐Shu

doi:10.1002/pat.5119

Cited by 10 publications

(11 citation statements)

References 22 publications

(25 reference statements)

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“…Therefore, PI(SDA-ODPA) can efficiently imidize at a low temperature to inhibit the dissolution rate in the exposed area, while maintaining a high dissolution rate in the unexposed area. In addition, PI(SDA-ODPA) presents a much lower D 0.5 than the reported values for chain extendable PI(ODA-BPDA) (152 mJ/cm 2 ), 15 PI(ODA-PMDA) (220 mJ/cm 2 ), 17 PI(SDA-BPDA) (38 mJ/cm 2 ), 18 PI(CHDA-BPDA) (70 mJ/cm 2 ), 19 PI(PDA-BPDA) (142 mJ/cm 2 ), 21 and PSPI with photosensitive o-nitrobenzyl ether group (2000 mJ/cm 2 ). 30…”

Section: Photosensitivitycontrasting

confidence: 60%

“…Both positive‐ and negative‐type PSPIs were developed based on a chain extendable poly(amic acid) (PAA), a thermally degradable crosslinker, and a photoacid generator (PAG) or a photobase generator (PBG), respectively 14,15 . Accordingly, the mechanical property of these PSPIs are modulated by the amount of crosslinker and the molecular weight of PAA, which is controlled by an anhydride‐based chain extender to end‐cap the prepolymer of PAA 15 . In addition, PSPI with good dimensional stability at high temperatures is getting considerable attention recently.…”

Section: Introductionmentioning

confidence: 99%

“…Both positive-and negative-type PSPIs were developed based on a chain extendable poly(amic acid) (PAA), a thermally degradable crosslinker, and a photoacid generator (PAG) or a photobase generator (PBG), respectively. 14,15 Accordingly, the mechanical property of these PSPIs are modulated by the amount of crosslinker and the molecular weight of PAA, which is controlled by an anhydride-based chain extender to end-cap the prepolymer of PAA. 15 In addition, PSPI with good dimensional stability at high temperatures is getting considerable attention recently.…”

Section: Introductionmentioning

confidence: 99%

“…14,15 Accordingly, the mechanical property of these PSPIs are modulated by the amount of crosslinker and the molecular weight of PAA, which is controlled by an anhydride-based chain extender to end-cap the prepolymer of PAA. 15 In addition, PSPI with good dimensional stability at high temperatures is getting considerable attention recently. Gao et al reported a negative-type PSPI based on a PAA consisting of 3,3 0 ,5,5 0 -tetramethyl-4,4 0 -diaminodiphenylmethane (TMMDA), 2,2 0 -bis(trifluoromethyl)-4,4 0 -bis[4-(4-amino-3methyl) benzamide] biphenyl (MABTFMB), and 3,3 0 ,4,4 0benzophenonetetracarboxylic dianhydride (BTDA).…”

Section: Introductionmentioning

confidence: 99%

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Investigating the structure–sensitivity relationship of photosensitive polyimide formulated by using a photobase generator

Chang

Tseng

et al. 2023

Journal of Polymer Science

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Photosensitive polyimides (PSPIs) have been widely used in the buffer coating layer and insulation layer due to their excellent thermal and mechanical stability. In this work, a series of negative‐type PSPIs based on poly(amic acid) (PAA) and a photobase generator (PBG) have been developed. Two diamines of 4,4′‐oxydianiline (ODA), 3,3′‐diaminodiphenyl sulfone (SDA), and four dianhydrides of pyromellitic dianhydride (PMDA), 3,3′,4,4′‐biphenyltetracarboxylic dianhydride (BPDA), 4,4′‐oxydiphthalic anhydride (ODPA) and cyclobutene‐1,2,3,4‐tetracarboxylic dianhydride (CBDA) are copolymerized to PAA through polyaddition, and the PAA is further thermally imidized to polyimide (PI). Through scrutinizing the structure–sensitivity relationship of these PIs, we find that the rigidity and transparency of the PAA/PI backbone play an important role in the sensitivity and contrast of PSPI. Accordingly, PSPI (SDA‐ODPA), possessing high optical transparency and a low rigidity represented by the low glass transition point, is capable of providing good photosensitivity of 30 mJ/cm2, a high contrast of 2.46, and an excellent pattern resolution of 4 μm after optimizing the prebaking (100°C for 5 min), exposure dose (380 mJ/cm2), post‐exposure baking (130°C for 7 min), and development parameters. This work provides the concept of structural design for negative‐type PSPI in the microelectronic application.

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Section: Photosensitivitycontrasting

confidence: 60%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Investigating the structure–sensitivity relationship of photosensitive polyimide formulated by using a photobase generator

Chang

Tseng

et al. 2023

Journal of Polymer Science

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“…But the PIMELTM BL‐301 has only 60% imidization index at 200°C and has poor heat resistance. Yao Ming Yeh et al [ 31 ] successfully prepared a Low‐temperature curable photosensitive polyimide. However, the mechanical properties of this PI are very poor, with a Young's modulus of only 1.75 GPa.…”

Section: Introductionmentioning

confidence: 99%

Low‐dielectric and low‐temperature curable fluorinated nano carbon/polyimide composites with 6‐aminoquinoline for end capping

Zhang

Sui

et al. 2022

Polymer Composites

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One challenge in the high-performance dielectric material of polyimide (PI) is to obtain the excellent comprehensive properties at low curing temperature for advanced IC package. In this work, 6-aminoquinoline (AQL) is introduced through covalent bonds for end capping to obtain a low-temperature curable PI at first. The results demonstrate that with very limited introduce (2.76%) of AQL, the imidization index could reach as high as 1.01 at 200 C. Then, fluorinated nano carbon (FC) is further introduced resulting in the fluorinated nano carbon/polyimide (FCPI) composites, which effectively reduces the dielectric constant (1 wt%, 2.75 @ 1 MHz). Besides, the as-prepared FCPIs also possess excellent thermal property of which FCPI-0.3 exhibited the 5% weight loss temperature of 540 C and the glass transition temperature is also as high as 385 C. Furthermore, the tensile strength of the film is 127 MPa, the elongation at break is around 15.82%, and the Youngs' modulus is about 3.10 GPa proving the superior mechanical property. As a result, the successful preparation of the FCPI nanocomposites not only possess low-temperature curing and lowdielectric performance but also exhibit excellent thermal and mechanical properties, which shows a wide range of application prospects in the field of microelectronics for the advanced electronic package.advanced electronic packaging, low dielectric constant, low temperature curing, polyimide | INTRODUCTIONWith the rapid development of microelectronic industry, electronic components tend to be miniaturized and chip interconnection density has also increased sharply. [1][2][3] Fan-out wafer-level packaging (FOWLP) has been one of the latest packaging forms with the ultrathin redistribution layer (RDL) and higher I/O density. [4,5] Thereinto, polyimide (PI) has become one of the most important dielectronic materials in RDL with superior thermal, mechanical property, low dielectronic constant and high chemical resistance and adhesion on various substrates. [6][7][8] However, new requirements have been appeared with the upcoming applications of 5G, AI, automate drive, internet of Jialin Zhang and Yuying Sui contributed equally to this study.

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Exploring the Impact of Blend and Graft of Quinoline Derivative in Low‐Temperature Curable Polyimides

Huang,

Lv,

Zhang

et al. 2023

Macromol. Rapid Commun.

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The utilization of accelerators has been a common approach to prepare low‐temperature curable polyimide (PI). However, the accelerators have gradually fallen out of favor because of their excessive dosages and negative effect on the properties of PI. In this work, a new strategy of introducing accelerators by grafting to eliminate these disadvantages is presented. A novel quinoline derivative named NQL was designed for this purpose, and an ultra‐low dosage of only 2.5 mol% was sufficient to prepare low‐temperature curable PI. The favorable low‐temperature curing effect of NQL was attributed to its strong alkalinity (pKa = 18.47) and electron‐donating ability (HOMO = ‐6.22 eV). At a curing temperature of 200 °C, the PI with 2.5 mol% NQL showed outstanding properties (Young's modulus of 5.73 GPa, elongation of 37.3%, tensile strength of 237 MPa and coefficient of thermal expansion of 16 ppm/K). In particular, NQL could even lower the curing temperature to 180 °C and the ultra‐low temperature curable PI film still retained excellent properties. These results demonstrate that introducing low‐temperature curable accelerators by partial grafting instead of blending is a promising way to furnish low‐temperature curable PI, and provide insights into the preparation of polyimide with high performance in advanced packaging.This article is protected by copyright. All rights reserved

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Low‐temperature curable, alkaline‐developable, and negative‐type photosensitive polyimide with high resolution and mechanical properties based on chain extendable poly(amic acid) and photo‐base generator

Cited by 10 publications

References 22 publications

Investigating the structure–sensitivity relationship of photosensitive polyimide formulated by using a photobase generator

Investigating the structure–sensitivity relationship of photosensitive polyimide formulated by using a photobase generator

Low‐dielectric and low‐temperature curable fluorinated nano carbon/polyimide composites with 6‐aminoquinoline for end capping

Exploring the Impact of Blend and Graft of Quinoline Derivative in Low‐Temperature Curable Polyimides

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