Organosoluble and optically transparent fluorine-containing polyimides based on 4,4′-bis(4-amino-2-trifluoromethylphenoxy)-3,3′,5,5′-tetramethylbiphenyl

Yang, Chin‐Ping; Hsiao, Sheng‐Huei; Chen, Kuei-Hung

doi:10.1016/s0032-3861(02)00359-2

Cited by 86 publications

(57 citation statements)

References 21 publications

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“…This could be interpreted by the high fluorine loadings in the polymer backbones, which resulted in the weakened intermolecular cohesive force due to the lower polarizability of the C-F bond, [20] which would also resulted in the improvements in polyimide solubility in organic solvents. [41] In other words, these results can be attributed to the reduction of the intermolecular chargetransfer complex (CTC) between alternating electrondonor (diamine) and electron-acceptor (dianhydride) moieties. The bulky and electron withdrawing -CF 3 and -C(CF 3 ) 2 À groups in diamine and 6FDA, respectively, was effective in decreasing CTC formation between polymer chains in PIEI-c through steric hindrance and the inductive effect (by decreasing the electron-donating property of diamine moieties).…”

Section: Optical Transparency and Photophysical Properties Of Pieismentioning

confidence: 99%

Organosoluble, thermally stable and low dielectric constant fluorinated polyimides containing 2,4,5-triphenylimidazole moiety in the main chains

Ghaemy

Berenjestanaki

Bazzar

2013

Designed Monomers and Polymers

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A photoactive highly fluorinated diamine was synthesized, characterized, and used in preparation of structurally confirmed poly(imidazole-ether-imide)s (PIEIs). These polymers showed excellent solubility, moderate viscosities, good thermal stability (T g = 230-280°C, T i = 390-435°C, T 10% = 480-510°C), low dielectric constant (2.60-2.76), and water absorptions. The PIEIs films showed highly optical transparency with light transmittance at 550 nm of as high as 80% and cutoff wavelength of as low as 390 nm. These polymers exhibited fluorescence emission peaks around 410-490 nm with the quantum yields measured in solution varied from 12 to 32%.

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Section: Optical Transparency and Photophysical Properties Of Pieismentioning

confidence: 99%

Organosoluble, thermally stable and low dielectric constant fluorinated polyimides containing 2,4,5-triphenylimidazole moiety in the main chains

Ghaemy

Berenjestanaki

Bazzar

2013

Designed Monomers and Polymers

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“…Fluorinated polyimides have attracted much attention in the electronics industry because of their properties such as low dielectric constant, low moisture absorption, low permittivity, and high thermal and chemical resistance due to the high electronegativity of fluorine atoms and low electron polarizability of CÀ ÀF bonds. [14][15][16][17] Incorporation of fluorine also enhances the solubility. 18 Solubilizations have been tried by several means such as introduction of flexible linkages, 19,20 bulky substituents, 21,22 or bulky units in the polymer backbone, [23][24][25] noncoplanar, 26,27 or alicyclic 28 monomers.…”

Section: Introductionmentioning

confidence: 99%

Thermal, mechanical, and dielectric properties of novel fluorinated copoly(imide siloxane)s

Ghosh

Banerjee

2008

J of Applied Polymer Sci

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Eight new poly(imidesiloxane)s copolymers have been prepared by one-pot solution imidization method. The polymers are made by the reaction of bisphenol-A dianhydride (BPADA) with four different fluorinated diamines and amino-propyl terminated polydimethylsiloxane (APPS). The polymers are named as 1a, 1b, 1c, and 1d, respectively, with a siloxane loading of 40 wt %. The second series of polymers where siloxane loading is 20 wt % were named as 1e, 1f, 1g, and 1h. The resulting polymers have been well-characterized by GPC, IR, and NMR techniques. The proton NMR indicates the siloxane loading is about 36-38% for the first series of polymers 1a-1d and a loading of 17-18% for the series of polymers 1e-1h. The films of these polymers showed low water absorption of 0.02% for the first series of polymers and 0.11% for the second series of polymers. Thermal, mechanical, and dielectric properties of these polymers have been evaluated and compared with their nonsiloxane analogues. Preliminary investigations of melt processability of these polymers were also investigated.

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“…2,2-Bis(4-hydroxyphenyl)hexafluoropropane (6F-bisphenol-A; Acros), 1,4-bis(4-amino-2-trifluoromethylphenoxy)benzene (mp 132-133 C, II a ), 24 1,2-bis(4-amino-2-trifluoromethylphenoxy)benzene (mp 116-117 C, II b ), 25 4,4 0 -bis(4-amino-2-trifluoromethylphenoxy)biphenyl (mp 155-156 C, II c ), 12 4,4 0 -bis(4-amino-2-trifluoromethylphenoxy)-3,3 0 ,5,5 0 -tetramethylbiphenyl (mp 256-257 C, II d ), 26 2,2-bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]propane (mp 131-132 C, II e ), 27 2,2-bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]hexafluoropropane (mp 65-66 C, II f ), 28 9,9-bis[4-(4-amino-2-trifluoromethylphenoxy)-phenyl]fluorene (mp 239-240 C, II g ), 29 4,4 0 -bis(4-aminophenoxy)biphenyl (mp 137-138 C, II f , Chriskev) were used as received. Commerially available aromatic dianhydrides including PMDA (Lancaster), BTDA (Acros), and ODPA (Chriskev) were recrystallized from acetic anhydride before use.…”

Section: Methodsmentioning

confidence: 99%

Organo-soluble and Lightly-colored Fluorinated Polyimides Based on 2,2-Bis[4-(3,4-dicarboxyphenoxy)phenyl]hexafluoropropane Dianhydride and Aromatic Bis(ether amine)s Bearing Pendent Trifluoromethyl Groups

Yang

Hsu

2006

Polym J

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ABSTRACT:Two series of soluble and light-colored poly(ether imide)s (III and IV) were synthesized from 2,2-bis [4-(3,4-dicarboxyphenoxyl)phenyl]hexafluoropropane dianhydride (I) and various fluorinated and non-fluorinated aromatic diamines (II a{g and II 0 a{g ) by a conventional two-step procedure that included a ring-opening polyaddition to give poly(amic acid)s, followed by chemical cyclodehydration to poly(ether imide)s. The III series were lighter-colored and higher optical transparency as compared with the non-fluorinated IV series. On comparing the IV series with the common lightly-colored aromatic polyimides (V series) based on 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride (6FDA), the IV series revealed less colored than the V series. This indicated that both the III and IV series were lightly-colored poly(ether imide)s. These polymer films showed the cutoff wavelength in the range of 364-371 nm. The III series showed good solubility in all testing solvents at a concentration of 5-10 wt/v % and most of IV series was soluble. These polymers exhibited glass-transition temperatures in the range of 194-264 C, and the 10% weight-loss temperatures were higher than 492 C under either nitrogen or air atmosphere. The III series also showed lower dielectric constants of 3.01-3.65 at 1 MHz and lower moisture absorption of 0.09-0.44 wt % than IV series.

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Organosoluble and optically transparent fluorine-containing polyimides based on 4,4′-bis(4-amino-2-trifluoromethylphenoxy)-3,3′,5,5′-tetramethylbiphenyl

Cited by 86 publications

References 21 publications

Organosoluble, thermally stable and low dielectric constant fluorinated polyimides containing 2,4,5-triphenylimidazole moiety in the main chains

Organosoluble, thermally stable and low dielectric constant fluorinated polyimides containing 2,4,5-triphenylimidazole moiety in the main chains

Thermal, mechanical, and dielectric properties of novel fluorinated copoly(imide siloxane)s

Organo-soluble and Lightly-colored Fluorinated Polyimides Based on 2,2-Bis[4-(3,4-dicarboxyphenoxy)phenyl]hexafluoropropane Dianhydride and Aromatic Bis(ether amine)s Bearing Pendent Trifluoromethyl Groups

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