US20040127632A1 - Perfluorostyrene compound, and coating solution and optical waveguide device using the same - Google Patents

Perfluorostyrene compound, and coating solution and optical waveguide device using the same Download PDF

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US20040127632A1
US20040127632A1 US10616889 US61688903A US2004127632A1 US 20040127632 A1 US20040127632 A1 US 20040127632A1 US 10616889 US10616889 US 10616889 US 61688903 A US61688903 A US 61688903A US 2004127632 A1 US2004127632 A1 US 2004127632A1
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compound
optical
formula
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fluorine
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Ji-Hyang Kim
Jae-il Kim
Tae-Kyun Kim
Hyung Lee
Seon Han
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KIM MI-HWA
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Zen Photonics Co Ltd
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00Ethers; Compounds having groups, groups or groups
    • C07C43/02Ethers
    • C07C43/20Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00Ethers; Compounds having groups, groups or groups
    • C07C43/02Ethers
    • C07C43/257Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/29Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing halogen
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F214/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
    • C08F214/18Monomers containing fluorine
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; MISCELLANEOUS COMPOSITIONS; MISCELLANEOUS APPLICATIONS OF MATERIALS
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS, OR APPARATUS
    • G02B6/00Light guides
    • G02B6/10Light guides of the optical waveguide type
    • G02B6/12Light guides of the optical waveguide type of the integrated circuit kind
    • G02B6/13Integrated optical circuits characterised by the manufacturing method
    • G02B6/138Integrated optical circuits characterised by the manufacturing method by using polymerisation
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00Systems containing at least three condensed rings
    • C07C2603/02Ortho- or ortho- and peri-condensed systems
    • C07C2603/04Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18Fluorenes; Hydrogenated fluorenes

Abstract

Disclosed is a fluorine compound having perfluorostyrene introduced at a terminal thereof, as represented in the following Formula 1, and a coating solution and an optical waveguide device using the same, characterized in that the introduction of perfluorostyrene results in a facile fabrication of thin films by a UV curing or a thermal curing, high thermal stability and chemical resistance, and low optical propagation loss and birefringence:
Figure US20040127632A1-20040701-C00001
Wherein Z is O or S; RF is an aliphatic or aromatic group; y is a natural number of 1-10; y′ is an integer of 0-1; x is an integer of 0-200; and
Figure US20040127632A1-20040701-C00002
Wherein B is a single bond or selected from the group consisting of —CO—, —SO2—, —S— and —O—, and Hal is selected from the group consisting of F, Cl, Br and I.

Description

    BACKGROUND OF THE INVENTION
  • [0001]
    1. Field of the Invention
  • [0002]
    The present invention relates, in general, to perfluorostyrene compounds, and coating solutions and optical waveguide devices using the same. In particular, the present invention is directed to a fluorine compound having perfluorostyrene moiety, and a coating solution and an optical waveguide device using the same. These fluorinated compounds are applied for a core and a cladding material of various planar optical waveguide devices, such as optical switches, variable optical attenuators (VOA), tunable and fixed wavelength filters, arrayed waveguide grating (AWG) devices, etc.
  • [0003]
    2. Description of the Related Art
  • [0004]
    Generally, polymeric optical waveguide devices should be required the reliability based on Telcodia test for the optical communication network. In such a case, the polymer material should have very high thermal stability and environmental stability. Further, there are required accurate control of a refractive index and low birefringence as well as low optical propagation loss at a telecommunication wavelength region. Furthermore, in order to fabricate a desirable optical device, the polymer material should have excellent adhesion to any substrate. Of the above-mentioned requirements, the optical propagation loss and the birefringence are regarded as very important characteristics. The optical propagation loss on a polymer thin film is mainly caused by the light absorption by a harmonic overtone vibration mode of a C—H bond in the presence of polymer. Such light absorption at wavelengths of near far infrared can be decreased by substituting deuterium (D) or halogen elements, such as fluorine (F), for hydrogen of C—H bond (or O—H, N—H), whereby an absorption wavelength band can be shifted to 5-25 μm. Therefore, the loss can be lowered at communication wavelengths.
  • [0005]
    On the other hand, the birefringence of the thin film is caused by a molecular structure and a stress of a thin film-preparing process.
  • [0006]
    Accordingly, various polymer materials have been developed to meet all the requirements. In this regard, a fluorinated polyimide compound, which is known to have excellent heat resistance, even at about 400° C., has been continuously applied for optical waveguide devices (U.S. Pat. No. 5,598,501, Macromolecules, vol 27, pp 6665, 1994 and Electronics Letters, 29(3) 269, 1993). However, polyimide suffers from drawbacks, such as relatively high optical loss of 0.7 dB/cm or more and a high birefringence of 0.008 or more.
  • [0007]
    As another polymer material, there is proposed UV-curable fluorinated acrylate including various compositions, which is advantageous in terms of relatively low optical loss of 0.3 dB/cm at 1.55 μm and a birefringence of 0.0008. (U.S. Pat. No. 6,306,563 B1, and IEEE Journal of selected topics in quantum electronics vol. 6, pp 54, 2000).
  • [0008]
    As still another polymer material, there is proposed fluorinated polyarylene ether having a low dielectric constant, and excellent mechanical strength and processability (U.S. Pat. No. 5,115,082), which shows the possibility as a potential optical polymer. In addition, the above polymer system is added with a thermally curable reactive group, to drastically increase chemical resistance, whereby such a polymer is applied for the optical waveguide device (Korean Patent No. 226,442). Consequently, fluorinated polyarylene ether based polymers have been further improved in optical loss (0.4 dB/cm) and birefringence (0.004), compared to polyamide-based polymers, but is disadvantageous of still high birefringence and high processing temperatures (280° C. or more).
  • SUMMARY OF THE INVENTION
  • [0009]
    To avoid the problems encountered in the related art, perfluorostyrene is introduced at a terminal of a compound for use in an optical device, whereby inherent light absorption caused by a higher order harmonic vibration mode of a C—H bond in the compound can be prevented in optical communication wavelength, thus realizing low optical loss, low optical birefringence, precise control of a refractive index, and a fabrication of optical devices at low temperatures in a short process time.
  • [0010]
    Therefore, it is the object of the present invention to provide a fluorinated compound having perfluorostyrene introduced at a terminal thereof.
  • [0011]
    Another object of the present invention is to provide a coating solution using the fluorinated compound.
  • [0012]
    Still another object of the present invention is to provide an optical waveguide device using the fluorinated compound.
  • BRIEF DESCRIPTION OF THE DRAWINGS
  • [0013]
    The above and other objects, features and other advantages of the present invention will be better understood from the following detailed description taken in conjunction with the accompanying drawings, in which:
  • [0014]
    [0014]FIG. 1 shows the refractive index according to blending ratio of fluorinated compounds of the present invention; and
  • [0015]
    [0015]FIG. 2 shows the precise control of refractive index according to blending ratio of coating solutions of the present invention.
  • DETAILED DESCRIPTION OF THE INVENTION
  • [0016]
    Based on the present invention, a fluorinated compound having perfluorostyrene introduced at a terminal thereof is synthesized through a reaction of polyol and pentafluorostyrene, which is represented by the following Formula 1:
    Figure US20040127632A1-20040701-C00003
  • [0017]
    Wherein Z is O or S; RF is an aliphatic or aromatic group; y is a natural number of 1-10; y′ is an integer of 0-1; x is an integer of 0-200; and
    Figure US20040127632A1-20040701-C00004
  • [0018]
    Wherein B is a single bond or selected from the group consisting of —CO—, —SO2—, —S— and —O—; and Hal is selected from the group consisting of F, Cl, Br and I.
  • [0019]
    Preferably, the fluorinated polymer compound having perfluorostyrene introduced at a terminal thereof is represented by the following Formula 2 in which y and y′ are 1:
    Figure US20040127632A1-20040701-C00005
  • [0020]
    Wherein Z is O or S, preferably O, and preferred RF is —CH2(CF2)nCH2—, —CH2CF2O(CF2CF2O)nCF2CH2—, or
    Figure US20040127632A1-20040701-C00006
  • [0021]
    Wherein x is an integer of 0-200, and preferably 2-50; D is selected from the group consisting of —C(CF3)2—, —C(CH3)2—, —CO—, —SO2—, —O— and —S—; R1 and R2 are independently selected from the group consisting of H, or halogen elements, such as F, Cl, Br and I; and m is a natural number of 1-3.
  • [0022]
    Represented by Formula 2 in which Z is O; x is an integer of 2-50; Ar is halogenated pentafluorobenzene; and RF is —CH2 (CF2)nCH2—, —CH2CF2 (OCF2CF2)nOCF2CH2— or
    Figure US20040127632A1-20040701-C00007
  • [0023]
    the perfluorostyrene-introduced fluorine compound can be synthesized.
  • [0024]
    In case where x and y′ are 0 in Formula 1, the perfluorostyrene-introduced fluorine compound is represented by the following Formula 3:
    Figure US20040127632A1-20040701-C00008
  • [0025]
    Wherein RF is an aliphatic or aromatic compound, and y is a natural number of 1-10. Preferably, Z is O, and RF is a substituted or unsubstituted alkyl group when y is 1, and RF is the same as RF of Formula 2 when y is 2.
  • [0026]
    In addition, the fluorine compound having perfluorostyrene introduced at a terminal thereof can be synthesized, as represented by Formula 3 in which RF is —CH2 (CF2)nCH2—, —CH2CF2 (OCF2CF2)nOCF2CH2—, or
    Figure US20040127632A1-20040701-C00009
  • [0027]
    when y is 2.
  • [0028]
    Further, the fluorine compound having perfluorostyrene introduced at a terminal thereof can be synthesized, as represented by Formula 3 in which when y is 3, RF is an aromatic or aliphatic group, and more preferably,
    Figure US20040127632A1-20040701-C00010
  • [0029]
    Wherein M is selected from the group consisting of C—CH3, C—CF3, C—CCl3, and C—CBr3, or selected from the group consisting of N, P and P═O.
  • [0030]
    Furthermore, it is possible to synthesize the perfluorostyrene-introduced fluorine compound as represented by Formula 3 in which -Z-RF is an aromatic or aliphatic polyol when y is 4 or more.
  • [0031]
    The fluorine compound represented by Formula 2 can be synthesized by reaction of an aliphatic or aromatic diol and a fluorinated aromatic compound in the presence of a base such as NaOH or K2CO3 in DMAc (dimetylacetamide). The reaction mixture was stirred at room temperature for ambient hours. And then to this mixture, pentafluorostyrene was added and stirred for more hours for complete reaction.
  • [0032]
    Below, Formula 4 shows representative the polymers having perfluorostyrene introduced at a terminal thereof. In addition to the chemical structures shown in Formula 4, derivatives substituted at a para-position through the above reaction may be produced with any amounts. Such derivatives are used without additional separation, to control the refractive index of an optical waveguide. In Formula 4, ‘a’ as a repeat unit number is preferably 2-50.
    Figure US20040127632A1-20040701-C00011
  • [0033]
    In addition, the compound represented by Formula 3 can be prepared by the reaction of selected from alcohol-containing RF, preferably diol or triol, and pentafluorostyrene in the presence of a base such as NaOH or K2CO3 in DMAc (dimethylacetamide).
  • [0034]
    Thereby, the representative fluorinated compounds having perfluorostyrene introduced at a terminal thereof are obtained, as represented by the following Formulas 5 and 6. In addition to the chemical structures shown in Formulas 5 and 6, derivatives substituted at a para-position through the above reaction may be produced with any amounts. As such, the derivatives are used without additional separation for the control of a refractive index and curing characteristics of an optical waveguide device. Below, the compounds represented by Formula 5 are ones in which y is 2 in Formula 3, and the compounds represented by Formula 6 are ones in which y is 3 in Formula 3:
    Figure US20040127632A1-20040701-C00012
  • [0035]
    Meanwhile, a polymer material for application of optical waveguide device is used as a mixture comprising the fluorine compound having perfluorostyrene introduced at a terminal thereof, as represented by Formula 2 or 3, a photoinitiator and a reactive fluorinated acrylate compound represented by the following Formula 7, so as to control the refractive index and viscosity.
  • [0036]
    In such a case, the photoinitiator is not particularly limited so long as it can initiate a reaction of a styrene group, which is exemplified by Irgacure 184, Irgacure 651, etc., sold by CIBA GEIGY:
    Figure US20040127632A1-20040701-C00013
  • [0037]
    Wherein A is a fluorinated aliphatic or aromatic group, and Y is H or CH3.
  • [0038]
    In particular, it is preferred that A is —CH2 (CF2)nCH2—, —CH2CF2 (OCF2CF2)nOCF2CH2— or
    Figure US20040127632A1-20040701-C00014
  • [0039]
    The compound represented by Formula 7 is obtained by the reaction of a fluorinated diol with acryloyl chloride in the presence of triethylamine. Synthesized acrylate compounds are represented by the following Formula 8:
    Figure US20040127632A1-20040701-C00015
  • [0040]
    Further, with the aim of achieving a desired curing density, a formation of multi-layered thin films and a high adhesion to a substrate, a polymer material suitable for application in the optical waveguide device can be used as a mixture of the fluorine compound represented by Formula 1, the photoinitiator and the acrylate compound represented by Formula 7 or commercially available acrylate compound, such as 1,6-hexanediol diacrylate, tris(2-hydroxy ethyl)isocyanurate triacrylate, and pentaerythrol triacrylate.
  • [0041]
    More particularly, as for a coating solution for use in the formation of a core layer and a cladding layer in the optical waveguide device, at least one fluorine compound represented by Formula 1 is mixed with the photoinitiator and the compound of Formula 7 or the reactive compound and solvents are added as necessary. To produce a coating solution, perfluorostyrene introduced at a terminal thereof dissolved in propylene glycol methyl ether acetate (PGMEA) or cyclohexanone, the photoinitiator and the compound (Formula 7) or commercially available reactive acrylate were blended. And then the solution was filtered with a Teflon membrane filter to remove fine particles having a size of 0.2 μm or more. Thereafter, the filtered solution is spin-coated onto various types of substrates, preferably, a silicon wafer substrate, and then subjected to a UV curing by the use of a UV irradiating apparatus in a nitrogen atmosphere, thereby obtaining a desired thin film.
  • [0042]
    Preferably, the coating mixture comprises 30-70 wt % of the fluorine compound selected from the group consisting of fluorine compounds of Formula 1, 30-70 wt % of acrylate selected from the group consisting of acrylate compounds of Formula 7 or 8, and 0.5-4 wt % of the photoinitiator.
  • [0043]
    The optical waveguide device using the fluorine compound includes a lower cladding layer, a core layer and an upper cladding layer, laminated sequentially on a planar substrate. In such a case, the core layer and the upper and lower cladding layers are formed of the fluorine compound.
  • [0044]
    As for the fabrication of the optical waveguide device, examples of the substrate for use in the polymer device include polymer plate, glass, silica plate and so on. Preferably, a silicon wafer substrate is used. As a lower cladding, a silica layer is formed or a polymer material having a refractive index lower than that of a polymer constituting a core layer is coated on such a substrate and cured. The formation of a thin film accords to the above manner. An optical waveguide core material is coated on the lower cladding layer and cured, after which a photolithographic process is performed to form optical waveguide patterns. Using a reactive ion etching (RIE) process or an inductive coupled plasma (ICP) etching process, the core layer are etched. Finally, a polymer material for an upper cladding layer is coated on the core layer and cured. Thusly fabricated optical device is diced and polished, thus forming an end face of the device for input and output of light waves.
  • [0045]
    The fluorine compound having perfluorostyrene introduced at a terminal thereof has higher fluorine content, compared to acrylate compounds. Hence, inherent light absorption of the compound by vibrations of C—H bonds is prevented, thus lowering the optical loss in optical communication wavelength. In addition, the optical birefringence is very low, and thus the fabrication of the optical device with low polarization dependence becomes facile (Table 1). Further, since the inventive fluorine compound has no polar functional groups, the moisture absorption is low. Referring to FIG. 1, it can be seen that the mixture of fluorine compounds of the present invention has an influence on the control of the refractive index. By a UV curing or a thermal curing, a thin film can be easily formed, thus fabricating the optical waveguide device having excellent thermal stability and chemical resistance.
  • [0046]
    Having generally described this invention, a further understanding can be obtained by reference to specific examples which are provided herein for the purpose of illustration only and are not intended to be limiting unless otherwise specified.
  • EXAMPLE 1 Preparation of Compound Having Repeat Unit Represented by Formula A
  • [0047]
    3.0 g (16.12 mmol) of hexafluorobenzene and 5.17 g (19.70 mmol) of 2,2,3,3,4,4,5,5-octafluoro-1,6-hexanediol were placed into a 100 mL three-neck flask, to which 46 mL of a DMAc solvent was added to completely dissolve the reactants in the flask. 2.05 g of NaOH was further added into the flask, after which the resulting mixture was stirred at room temperature for 24 hours in a nitrogen atmosphere. Then, the reaction mixture was added with 1.39 g (7.16 mmol) of pentafluorostyrene and stirred for more 12 hours. Thusly obtained reaction mixture was extracted with deionized water and ether. The extracted ether layer was dried with magnesium sulfate, and ether was evaporated by a rotary evaporator. The produced liquid compound with very high viscosity was dried at room temperature using a vacuum pump to remove the residual solvent. 1H-NMR (Acetone d6): δ 4.90 (m), 5.75 (d of d), 6.04 (d of d), 6.68 (d of d). Mn=2,560 (NMR).
  • EXAMPLE 2 Preparation of Compound Having Repeat Unit Represented by Formula B
  • [0048]
    The present example was performed in the same manner as in example 1, with the exception being that 4.87 g (19.70 mmol) of bromopentafluorobenzene was used, instead of hexafluorobenzene. 1H-NMR (Acetone d6). δ 4.92 (m), 5.73 (d of d), 6.04 (d of d), 6.67 (d of d). Mn=2,900 (NMR).
  • EXAMPLE 3 Preparation of Compound Having Repeat Unit Represented by Formula C
  • [0049]
    2.26 g (12.15 mmol) of hexafluorobenzene and 6.09 g (14.85 mmol) of perfluorotetraethylene glycol were placed into a 100 mL three-neck flask, to which 47 mL of a DMAc solvent was added to completely dissolve the reactants in the flask. 1.54 g of NaOH was further added into the flask, after which the resulting mixture was stirred at room temperature for 24 hours in a nitrogen atmosphere. Then, the reaction mixture was added with 1.05 g (5.40 mmol) of pentafluorostyrene and stirred for 12 hours. Thusly obtained reaction mixture was extracted with deionized water and ether. The extracted ether layer was dried with magnesium sulfate, and ether was evaporated by a rotary evaporator. The produced liquid compound was dried at room temperature using a vacuum pump. 1H-NMR (CDCl3). δ 4.48(m), 5.66 (d of d), 6.03 (d of d), 6.59 (d of d). Mn=3,150 (NMR).
  • EXAMPLE 4 Preparation of Compound Having Repeat Unit Represented by Formula D
  • [0050]
    The present example was performed in the same manner as in example 3, with the exception being that 3.0 g (12.15 mmol) of bromopentafluorobenzene was used, instead of hexafluorobenzene. 1H-NMR (Acetone d6): δ 4.50 (m), 5.65 (d of d), 6.03 (d of d), 6.60 (d of d). Mn=3,470 (NMR)
  • EXAMPLE 5 Preparation of Compound Having Repeat Unit Represented by Formula E
  • [0051]
    3.0 g (16.12 mmol) of hexafluorobenzene and 6.62 g (19.70 mmol) of 2,2-bis (4-hydroxyphenyl)hexafluoropropane were placed into a 100 mL three-neck flask, to which 55 mL of a DMAc solvent was added to completely dissolve the reactants in the flask. 2.05 g of NaOH was further added into the flask, after which the resulting mixture was stirred at room temperature for 24 hours in a nitrogen atmosphere. Then, 1.39 g (7.16 mmol) of pentafluorostyrene was added to the reaction mixture, which was then stirred for 12 hours. The reaction mixture was extracted with deionized water and ether. The extracted ether layer was dehydrated with magnesium sulfate, and ether was evaporated by a rotary evaporator. The produced white solid compound was dried at 30° C. in a vacuum oven. 1H-NMR (Acetone d6): δ 5.80 (d of d), 6.09 (d of d), 6.74 (d of d), 7.26(d), 7.43 (d). Mn=2,980 (NMR).
  • EXAMPLE 6 Preparation of Compound Having Repeat Unit Represented by Formula F
  • [0052]
    In a 100 mL three-neck flask, 5.0 g (14.97 mmol) of decafluorobiphenyl and 6.15 g (18.29 mmol) of 2,2-bis(4-hydroxyphenyl)hexafluoropropane were completely dissolved in 63 mL of a DMAc solvent. Then, 1.90 g of NaOH was further added into the flask, after which the resulting mixture was stirred at room temperature for 24 hours in a nitrogen atmosphere. To this reaction 1.29 g (6.64 mmol) of pentafluorostyrene was added and stirred for ˜12 hours. The reaction mixture was extracted with deionized water and ether. The extracted ether layer was dehydrated with magnesium sulfate, and ether was evaporated by a rotary evaporator. The produced white solid compound was dried at 30° C. in a vacuum oven. 1H-NMR (Acetone d6): δ 5.82 (d of d), 6.11 (d of d), 6.75 (d of d), 7.30 (d), 7.43 (d). Mn=3,610 (NMR).
  • EXAMPLE 7 Preparation of Compound Represented by Formula Aa
  • [0053]
    In a 100 mL three-neck flask, 5.0 g (13.81 mmol) of 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoro-1,8-octanediol and 5.36 g (27.62 mmol) of pentafluorostyrene were completely dissolved in 59 mL of a DMAc solvent. 1.44 g of NaOH was further added into the flask. The resulting mixture was stirred at room temperature for 10 hours in a nitrogen atmosphere. Thusly obtained reaction mixture was cooled and then extracted with deionized water and ether. The extracted ether layer was dehydrated with magnesium sulfate, and ether was evaporated by a rotary evaporator. The produced white solid compound was dried at 30° C. in a vacuum oven. 1H-NMR (CDCl3): δ 4.48 (t, 4H), 5.67 (d of d, 2H), 6.05 (d of d, 2H), 6.61 (d of d, 2H)
  • EXAMPLE 8 Preparation of Compound Having Repeat Unit Represented by Formula Ac
  • [0054]
    The present example was performed in the same manner as in example 7, with the exception being that 5.66 g (13.81 mmol) of perfluorotetraethylene glycol was used, instead of 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoro-1,8-octanediol. 1H-NMR (CDCl3): δ 4.64 (t, 4H), 5.66 (d of d, 2H), 6.05 (d of d, 2H), 6.60 (d of d, 2H).
  • EXAMPLE 9 Preparation of Compound Represented by Formula Ab
  • [0055]
    5.0 g (14.87 mmol) of 2,2-bis(4-hydroxyphenyl)hexafluoropropane and 5.77 g (27.74 mmol) of pentafluorostyrene were placed into a 100 mL three-neck flask, to which 61 mL of a DMAc solvent was added to completely dissolve the reactants in the flask. 1.55 g of NaOH was further added into the flask, after which the resulting mixture was stirred at room temperature for 12 hours in a nitrogen atmosphere. Then, the reaction mixture was cooled and extracted with deionized water and ether. The extracted ether layer was dehydrated with magnesium sulfate, and ether was evaporated by a rotary evaporator. Finally, the produced white solid compound was dried at 30° C. in a vacuum oven. 1H-NMR (Acetone d6): δ 5.81 (d of d, 2H), 6.10 (d of d, 2H), 6.74 (d of d, 2H), 7.25 (d, 4H) 7.44 (d, 4H).
  • EXAMPLE 10 Preparation of Compound Represented by Formula Ad
  • [0056]
    5.0 g (14.27 mmol) of 9,9-bis (4-hydroxyphenyl) fluorene and 5.54 g (28.54 mmol) of pentafluorostyrene were placed into a 100 mL three-neck flask, and then completely dissolved with 60 mL of a DMAc solvent. 1.48 g of NaOH was further added into the flask. The resulting mixture was stirred at room temperature for 8 hours in a nitrogen atmosphere. Then, the reaction mixture was cooled and extracted with deionized water and ether. The extracted ether layer was dehydrated with magnesium sulfate, and ether was evaporated by a rotary evaporator. Finally, the produced white solid compound was dried at 30° C. in a vacuum oven. 1H-NHR (Acetone d6): δ 5.77 (d of d, 2H), 6.07 (d of d, 2H), 6.70 (d of d, 2H), 7.00 (d, 4H), 7.20 (d, 4H), 7.33 (t, 2H), 7.39 (t, 2H), 7.46(d, 2H), 7.88 (d, 2H).
  • EXAMPLE 11 Preparation of Compound Represented by Formula Ba
  • [0057]
    Into a 100 mL three-neck flask, 3.0 g (9.79 mmol) of 1,1,1-tris(4-hydroxyphenyl)ethane and 5.70 g (29.38 mmol) of pentafluorostyrene were placed and then completely dissolved with 49 mL of a DMAc solvent. 1.57 g of NaOH was further added into the flask. The resulting mixture was stirred at room temperature for 8 hours in a nitrogen atmosphere, after which the reaction mixture was extracted with deionized water and ether. The extracted ether layer was dehydrated with magnesium sulfate, and ether was evaporated by a rotary evaporator. The produced white solid compound was dried at 30° C. in a vacuum oven. 1H-NMR (Acetone d6): δ 2.16 (s, 3H), 5.78 (d of d, 3H), 6.08 (d of d, 3H), 6.73 (d of d, 3H), 7.04 (d, 6H), 7.10 (d, 6H)
  • EXAMPLE 12 Preparation of Compound Having Repeat Unit Represented by Formula Bb
  • [0058]
    The present example was performed in the same manner as in example 11, with the exception being that 1.23 g (9.79 mmol) of 1,2,4-benzenetriol was used, instead of 1,1,1-tris(4-hydroxyphenyl)ethane. 1H-NMR (Acetone d6): δ 5.3 (d of d, 3H), 5.4 (d of d, 3H), 6.3 (s, 3H), 6.9 (d of d, 3H).
  • EXAMPLE 13 Preparation of Compound Represented by Formula Cb
  • [0059]
    In a 100 mL three-neck flask, 5.0 g (13.81 mmol) of 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoro-1,8-octanediol was completely dissolved in 80 mL of a DMAc solvent. 3 g of triethylamine was further added into the flask. While a reactor was maintained at 0° C. or lower in a nitrogen atmosphere, acryloyl chloride was droplets slowly added to the reaction in the reactor, after which the reaction mixture was stirred for 3 hours. The reaction mixture was filtered to remove a formed ammonium salt, and extracted with deionized water and ether. The extracted ether layer was dehydrated with magnesium sulfate, and ether was evaporated by a rotary evaporator. The produced liquid compound was vacuum distilled to produce a pure compound. 1H-NMR (CDCl3): d 4.66 (t, 4H), 5.99 (d, 2H), 6.22 (q, 2H), 6.54 (d, 2H).
  • EXAMPLE 14 Preparation of Polymer Coating Solution Including Perfluorostyrene Compound Represented by Formula 1 or 2
  • [0060]
    Each fluorine compound having perfluorostyrene introduced at a terminal thereof, prepared in examples 1-12, was admixed with Irgacure 651 as a photoinitiator, and then dissolved in 10-100 wt % of PGMEA or cyclohexanone solvent, depending on viscosity. The solution was further mixed with a compound represented by Formula 5 and 10-60 wt % of reactive acrylate, to produce a coating solution, which was then filtered with a 0.2 μm Teflon filter. Thereby, a coating solution suitable for use in the core and cladding layers as thin films of an optical waveguide device was produced. The following Table 1 shows the refractive index and the optical loss of thin films formed after being cured, depending on the composition and the content of the composition.
    TABLE 1
    Exp. Content Refractive Light Loss
    No. Composition (wt %) index (dB/cm)
    1 Compound (B) 70 1.4540 0.16
    Photoinitiator 1
    (Irgacure 651)
    Solvent (PGMEA) 29
    2 Compound (C) 70 1.3910 0.15
    Photoinitiator 1
    (Irgacure 651)
    Solvent (PGMEA) 29
    3 Compound (D) 70 1.4110 0.17
    Photoinitiator 1
    (Irgacure 651)
    Solvent (PGMEA) 29
    4 Compound (F) 40 1.4930 0.21
    Photoinitiator 1
    (Irgacure 651)
    Solvent (PGMEA) 59
    5 Compound (B) 40 1.4790 0.3
    Compound (Ba) 15
    Photoinitiator 1
    (Irgacure 651)
    Solvent 44
    (cyclohexanone)
    6 Compound (B) 40 1.4450 0.34
    Compound (Cb) 30
    Compound (Cc) 10
    Pentaerythrol 19
    triacrylate
    Photoinitiator 1
    (Irgacure 651)
    7 Compound (B) 40 1.4320 0.31
    Compound (Cb) 25
    Compound (Cc) 25
    Pentaerythrol 9
    triacrylate
    Photoinitiator 1
    (Irgacure 651)
  • [0061]
    In Table 1, the refractive index was measured by a prism coupler, and the optical loss was determined by the incorporation of a slab waveguide using an index matching oil. The refractive index and the optical loss were measured at a wavelength of 1550 nm.
  • EXAMPLE 15 Precise Control of Refractive Index
  • [0062]
    In an optical waveguide device, precise control of refractive index is needed between the core and cladding layers in order to contain the single mode condition. For this, the coating solutions, having different refractive indexes as shown in example 14, were mixed together by a weight ratio. FIG. 2 shows the relationship between the refractive index and the coating solution mixture obtained by mixing the coating solutions shown in experimental numbers 6 and 7 of Table 1 in example 14.
  • EXAMPLE 16 Preparation of Polymer Thin Film Using Polymer Coating Solution Containing Perfluorostyrene Compound Represented by Formula 1 or 2
  • [0063]
    The polymer coating solution having perfluorostyrene, prepared in example 14, was filtered with a 0.2 μm Teflon filter. Of various types of substrates, a silicon wafer substrate was preferably used. Such a substrate was spin-coated with the filtered polymer coating solution at 500-5000 rpm, and cured under a UV light intensity of 5-200 mW/cm2, preferably 10-50 mW/cm2, using a mercury lamp in a nitrogen atmosphere for 2-30 min, and then post baked on a hot plate at 100-200° C. for 0.5-1 hour, to prepare a desired polymer thin film. The obtained thin film is superior in chemical resistance, thus realizing a facile fabrication of an optical device having multi-layered thin films.
  • EXAMPLE 17 Fabrication of Optical Device Using Polymer
  • [0064]
    As a substrate suitable for use in the fabrication of an optical device, a silicon wafer was used. As a lower cladding of the optical device, a silica layer was formed or the inventive polymer having a refractive index lower by about 0.3-1% than that of a core layer polymer was coated on the silicon wafer substrate, and then cured. The formation of the thin film was performed in the same manner as in example 16. A polymer core material was coated on the lower cladding layer and then cured, after which a photomask was aligned and a photolithographic process was performed, thereby forming optical waveguide patterns. Then, by the use of a reactive ion etching process or an inductive coupled plasma process, the core layer of the optical waveguide, were etched. Finally, the same polymer material as the coating solution used for the lower cladding layer was coated on the core layer and then cured, to obtain an upper cladding layer. Thereby, a desired optical waveguide device was fabricated. As necessary, a drive electrode forming process might be further performed for driving an optical device on the upper cladding layer. The fabricated optical device wafer was diced and polished by the use of a saw and a polisher, thereby forming an end face of the device for input and output of light waves.
  • [0065]
    As described above, the present invention provides a fluorine compound having perfluorostyrene introduced at a terminal thereof, and a coating solution and an optical waveguide device using such a fluorine compound. The fluorine compound has high fluorine content on a molecular structure thereof, whereby inherent light absorption due to molecular vibrations can be prevented in optical communication wavelength, thus decreasing optical loss.
  • [0066]
    Further, the optical birefringence of the thin film, which is attributed to a molecular structure of the film material, is remarkably reduced, and thus the optical device with low polarization dependence can be easily fabricated. Moreover, the fluorine compounds are mixed together, thereby achieving precise control of the refractive index. In addition, the fluorine compound has no polar functional groups, resulting in low moisture absorption. By a UV curing or a thermal curing, the thin film can be readily formed, thus obtaining an optical waveguide device having excellent thermal stability and chemical resistance.
  • [0067]
    The present invention has been described in an illustrative manner, and it should be understood that the terminology used is intended to be in the nature of description rather than of limitations. Many modifications and variations of the present invention are possible in light of the above teachings. Therefore, it should be understood that within the scope of the appended claims, the invention may be practiced otherwise than as specifically described.

Claims (15)

    What is claimed is:
  1. 1. A fluorine compound having perfluorostyrene introduced at a terminal thereof, as represented in the following Formula 1:
    Figure US20040127632A1-20040701-C00016
    Wherein Z is O or S; RF is an aliphatic or aromatic group; y is a natural number of 1-10; y′ is an integer of 0-1; x is an integer of 0-200; and
    Figure US20040127632A1-20040701-C00017
    Wherein B is a single bond or selected from the group consisting of —CO—, —SO2—, —S— and —O—; and Hal is selected from the group consisting of F, Cl, Br and I.
  2. 2. The fluorine compound as defined in claim 1, wherein y and y′ are 1, and RF is —CH2(CF2)nCH2—, —CH2CF2O(CF2CF2O)nCF2CH2—, or
    Figure US20040127632A1-20040701-C00018
    Wherein n is a natural number of 1-12; D is selected from the group consisting of —C(CF3)2—, —C(CH3)2—, —CO—, —SO2—, —O— and —S—; R1 and R2 are independently selected from the group consisting of H, or halogen elements, including F, Cl, Br and I; and m is a natural number of 1-3.
  3. 3. The fluorine compound as defined in claim 2, wherein Z is O, and x is an integer of 2-50.
  4. 4. The fluorine compound as defined in claim 3, wherein Ar is halogenated pentafluorobenzene, and RF is —CH2 (CF2)nCH2—, —CH2CF2 (OCF2CF2)nOCF2CH2— or
    Figure US20040127632A1-20040701-C00019
  5. 5. The fluorine compound as defined in claim 1, wherein y is a natural number of 1-10, and x and y′ are 0.
  6. 6. The fluorine compound as defined in claim 5, wherein y is 1, and RF is a substituted or unsubstituted alkyl group.
  7. 7. The fluorine compound as defined in claim 5, wherein y is 2, and Z is 0, and RF is —CH2(CF2)nCH2—, —CH2CF2O(CF2CF2O)nCF2CH2—, or
    Figure US20040127632A1-20040701-C00020
    Wherein n is a natural number of 1-12; D is selected from the group consisting of —C(CF3)2—, —C(CH3)2—, —CO—, —SO2—, —O— and —S—; R1 and R2 are independently selected from the group consisting of H, or halogen elements, including F, Cl, Br and I; and m is a natural number of 1-3.
  8. 8. The fluorine compound as defined in claim 7, wherein RF is —CH2(CF2)nCH2—, —CH2CF2(OCF2CF2)nOCF2CH2—, or
    Figure US20040127632A1-20040701-C00021
  9. 9. The fluorine compound as defined in claim 5, wherein y is 3, and RF is
    Figure US20040127632A1-20040701-C00022
    Wherein M is selected from the group consisting of C—CH3, C—CF3, C—CCl3, C—CBr3, N, P and P═O.
  10. 10. The fluorine compound as defined in claim 5, wherein y is a natural number of 4-10, and -Z-RF is an aromatic or aliphatic polyol.
  11. 11. A polymer coating solution, comprising at least one fluorine compound selected from the group consisting of fluorine compounds having perfluorostyrene introduced at a terminal thereof of claim 1, at least one acrylate compound selected from the group consisting of acrylate compounds represented by the following Formula 7, and a photoinitiator:
    Figure US20040127632A1-20040701-C00023
    Wherein A is a fluorinated aliphatic or aromatic group, and Y is H or CH3.
  12. 12. The polymer coating solution as defined in claim 11, wherein A is —CH2(CF2)nCH2—, —CH2CF2(OCF2CF2)nOCF2CH2— or
    Figure US20040127632A1-20040701-C00024
  13. 13. A polymer coating solution, comprising 30-70 wt % of at least one fluorine compound selected from the group consisting of fluorine compounds having perfluorostyrene introduced at a terminal thereof of claim 1, 30-70 wt % of at least one acrylate compound selected from the group consisting of acrylate compounds represented by the following Formula 7, and 0.5-4 wt % of a photoinitiator:
    Figure US20040127632A1-20040701-C00025
    Wherein A is a fluorinated aliphatic or aromatic group, and Y is H or CH3.
  14. 14. An optical waveguide device, comprising a lower cladding layer formed on a planar substrate, a core layer formed on the lower cladding layer, and an upper cladding layer formed on the core layer, wherein the core layer and the lower and upper cladding layers include the fluorine compound of any one of claims 1 to 10.
  15. 15. An optical waveguide device, comprising a lower cladding layer formed on a planar substrate, a core layer formed on the lower cladding layer, and an upper cladding layer formed on the core layer, wherein the core layer and the lower and upper cladding layers include the coating solution of claim 11 or 12.
US10616889 2002-07-12 2003-07-10 Perfluorostyrene compound, and coating solution and optical waveguide device using the same Abandoned US20040127632A1 (en)

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JP2006045159A (en) * 2004-08-06 2006-02-16 Asahi Glass Co Ltd Fluorine-containing ether and its use
JP2006076893A (en) * 2004-09-07 2006-03-23 Asahi Glass Co Ltd New fluorine-containing ether
US20060068207A1 (en) * 2004-09-28 2006-03-30 Brewer Science Inc., A Missouri Corporation Curable high refractive index resins for optoelectronic applications
US20080287624A1 (en) * 2004-09-14 2008-11-20 Maria Petrucci-Samija Process for Preparing an Optical Organic Polymer
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US6946534B2 (en) * 2000-09-28 2005-09-20 Mi-Hwa Kim Fluorinated polyethers having perfluorinated aliphatic group and optical waveguide using the same
JP2006045159A (en) * 2004-08-06 2006-02-16 Asahi Glass Co Ltd Fluorine-containing ether and its use
JP2006076893A (en) * 2004-09-07 2006-03-23 Asahi Glass Co Ltd New fluorine-containing ether
JP4661140B2 (en) * 2004-09-07 2011-03-30 旭硝子株式会社 Water and oil repellent solution composition, substrate and method of manufacturing
US20080287624A1 (en) * 2004-09-14 2008-11-20 Maria Petrucci-Samija Process for Preparing an Optical Organic Polymer
US20090087666A1 (en) * 2004-09-28 2009-04-02 Mercado Ramil-Marcelo L Curable high refractive index resins for optoelectronic applications
US20060068207A1 (en) * 2004-09-28 2006-03-30 Brewer Science Inc., A Missouri Corporation Curable high refractive index resins for optoelectronic applications
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US20160137809A1 (en) * 2013-08-07 2016-05-19 Asahi Glass Company, Limited Crosslinkable fluorinated elastomer composition and crosslinked product thereof
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