CN111909378A - Fluorinated polyurethane imide electro-optic waveguide material - Google Patents
Fluorinated polyurethane imide electro-optic waveguide material Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
- C08G73/128—Unsaturated polyimide precursors the unsaturated precursors containing heterocyclic moieties in the main chain
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1035—Preparatory processes from tetracarboxylic acids or derivatives and diisocyanates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1096—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors containing azo linkage in the main chain
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Abstract
The invention discloses a fluorinated polyurethane imide electro-optic waveguide material, belonging to the technical field of preparation of polymer optical waveguide materials. The fluorinated polyurethane imide electro-optic waveguide material prepared by the invention has the advantages of good film forming property, low optical transmission loss and higher electro-optic coefficient.
Description
Technical Field
The invention belongs to the technical field of preparation of polymer optical waveguide materials, and particularly relates to a fluorinated polyurethane imide electro-optic waveguide material.
Background
The organic polymer electro-optic waveguide material has great advantages in preparing optical waveguide electro-optic modulation devices in integrated optics. However, the optical transmission loss, the electrooptical coefficient and the polarization orientation stability of the chromophore group of the organic polymer electrooptical waveguide material are the most critical material factors for restricting the performance and the development of the organic polymer optical waveguide electrooptical device, and the organic polymer electrooptical waveguide material which integrates low optical transmission loss, high electrooptical coefficient and good polarization orientation stability of the chromophore group and meets the requirements of preparing the high-performance polymer optical waveguide electrooptical device is synthesized, and is one of the most important and challenging works in modern integrated optics. The design, preparation, development and application of the high-performance light wave conductive optical modulation device are mainly used for preparing the organic polymer electro-optic waveguide material with excellent comprehensive performance.
The polymer optical waveguide substrate materials used at present mainly comprise materials such as polymethyl methacrylate, polystyrene, polyurethane, polycarbonate, polyimide, polyether ketone and the like, and the polymer electro-optic waveguide materials are formed by doping or bonding the optical waveguide substrate materials with second-order nonlinear optical color-generating molecules with excellent optical performance. The research of the polymer electro-optic waveguide material relates to a plurality of polymer systems, and the polymer electro-optic waveguide material can be divided into a host-guest doped type, a side chain type, a main chain type, a cross-linking type, a binary chromophoric molecule composite polymer and the like according to the structural characteristics of a polymer matrix material and a chromophoric molecule system.
At present, the research on the synthesis of polymer electro-optic waveguide materials pays more attention to the synthesis of doped polymers, the reported electro-optic polymers with high electro-optic coefficients are basically doped, and the research on bonding electro-optic polymers with better comprehensive properties is not deep enough.
Disclosure of Invention
1. Technical problem to be solved by the invention
The invention aims to overcome the defects of the prior art and provides a fluorinated polyurethane imide electro-optic waveguide material, and by adopting the technical scheme of the invention, the fluorinated polyurethane imide electro-optic waveguide material with good film forming property, low optical transmission loss and higher electro-optic coefficient performance can be prepared, so that the fluorinated polyurethane imide electro-optic waveguide material can be used for preparing a polymer optical waveguide device.
2. Technical scheme
In order to achieve the purpose, the technical scheme provided by the invention is as follows:
the fluorinated polyurethane imide electro-optic waveguide material is a polymer with a Y-shaped structure, wherein a nitrogen-containing hydroxyl group in a chromophore molecule forms one part of a polymer main chain, and an electron conjugate bridge and an electron acceptor part in the chromophore molecule are bonded to the polymer main chain as side chains.
Further, the preparation method of the fluorinated polyurethane imide electro-optic waveguide material comprises the following specific steps:
(1) synthesizing a compound A containing a tricyanofuran structure from 3-hydroxy-3-methyl-2-butanone and malononitrile according to a molar ratio of 1: 2.1-2.3 under the catalysis of sodium ethoxide;
(2) carrying out diazo salt reaction on the p-aminobenzaldehyde and sodium nitrite with sulfuric acid according to the molar ratio of 1: 1.1-1.2, and then carrying out coupling reaction on the diazo salt and N, N-dihydroxyethyl aniline with the same molar amount as the p-aminobenzaldehyde to prepare an azo compound B;
(3) carrying out reflux reaction on the compound B and the compound A under the action of acetic acid and ammonium acetate to prepare a second-order nonlinear optical chromogenic molecule C containing tricyanofuran and a dihydroxy group;
(4) dissolving a chromophore C and 4, 4' -diphenylmethane diisocyanate in a molar ratio of 1: 2.1-2.2 in N-methylpyrrolidone, reacting at 30-40 ℃ for 1-2h, reacting at 60-75 ℃ for 1-2h, reacting at 85-95 ℃ for 2-3h, cooling to room temperature, adding hexafluorodianhydride with the same molar weight as the chromophore or adding hexafluorodianhydride with the same molar weight as one half of the chromophore into the reaction liquid, reacting at 30-40 ℃ for 2-3h, reacting at 85-95 ℃ for 2-3h, reacting at 155-175 ℃ for 8-12h, cooling to room temperature, dropping the reaction liquid into methanol aqueous solution with the same volume ratio, performing suction filtration, drying at 60 ℃ to obtain a crude product, dissolving the crude product in N, N-dimethylformamide, and then dropping into methanol aqueous solution with the same volume ratio, and (4) carrying out suction filtration and drying at 60 ℃ to obtain the purified fluorinated polyurethane imide electro-optic waveguide material.
The second-order nonlinear optical chromophore molecule C is a chromophore molecule having a D-pi-a (electron donor-electron conjugated bridge-electron acceptor) structure and containing two hydroxyl groups, the electron donor of the second-order nonlinear optical chromophore molecule C is an aniline containing dihydroxy as an electron donor, the electron acceptor is an electron acceptor containing nitrobenzene or Tricyanofuran (TCF) or Tricyanopyrroline (TCP) structure, and the conjugated pi-electron bridge is an electron acceptor containing benzene ring, C-C double bond, N-N double bond and one or more aromatic heterocycles containing thiophene, thiazole, pyrimidine, furan and benzothiazole as a conjugated pi-electron bridge.
The hexafluoro dianhydride is 4, 4' -hexafluoroisopropylidene phthalic anhydride.
3. Advantageous effects
Compared with the prior art, the technical scheme provided by the invention has the following remarkable effects:
(1) the invention relates to a fluorinated polyurethane imide electro-optic waveguide material, wherein the synthesized polymer electro-optic waveguide material is a bonding type electro-optic waveguide material, and has the performances of a main chain type electro-optic polymer and a side chain type electro-optic polymer on a polymer chain segment structure.
(2) The invention relates to a fluorinated polyurethane imide electro-optic waveguide material, and a preparation method of the polymer electro-optic waveguide material is based on synthesis of a second-order nonlinear optical chromophoric molecular monomer and synthesis of a polymer.
(3) The fluorinated polyurethane imide electro-optic waveguide material prepared by the preparation method has the advantages of good film forming property, high thermal stability, good polarization stability, high electro-optic coefficient and low optical waveguide transmission loss, and is expected to be used for preparing polymer optical waveguide devices.
Detailed Description
For a further understanding of the present invention, reference will now be made in detail to the following examples.
Example 1
In the fluorinated polyurethane imide electro-optic waveguide material of the embodiment, a chromophore molecule, diisocyanate and hexafluorodianhydride are subjected to tri-monomer polymerization to generate a polymer with a Y-type structure, wherein a nitrogen-containing hydroxyl group in the chromophore molecule forms a part of a polymer main chain, and an electron conjugate bridge and an electron acceptor part in the chromophore molecule are bonded to the polymer main chain as side chains.
The preparation method of the fluorinated polyurethane imide electro-optic waveguide material comprises the following specific steps:
synthesis of (mono) second-order nonlinear optical chromophore C
Firstly, synthesizing a compound A containing a tricyanofuran structure from 3-hydroxy-3-methyl-2-butanone and malononitrile according to a molar ratio of 1: 2.1-2.3 under the catalysis of sodium ethoxide.
Specifically, in this embodiment: 4.0853g of 3-hydroxy-3-methyl-2-butanone, 5.5490g of malononitrile and 0.4g of sodium ethoxide are weighed to react for 1 hour at room temperature, then 20mL of ethanol is added to react for 1 hour under reflux, the temperature is reduced to room temperature, the mixture is filtered and filtered, and the ethanol is recrystallized, so that the compound A containing the tricyanofuran structure is obtained, wherein the chemical reaction equation is shown as the formula (1):
② diazo reacting aminobenzaldehyde and sodium nitrite with sulfuric acid according to the molar ratio of 1: 1.1-1.2.
Specifically, in this embodiment: 1.7565g of p-aminobenzaldehyde is weighed and added into 4mL of sulfuric acid, the mixture is cooled to below 5 ℃ by ice cubes, and 1.1006g of NaNO is dropwise added under ice bath2Reacting the aqueous solution for 2 hours to prepare the diazonium salt.
And step two, coupling reaction with N, N-dihydroxyethyl aniline in the same molar amount as p-aminobenzaldehyde to obtain azo compound B.
Specifically, in this embodiment: slowly dripping the diazonium salt solution into 2.6278g N, N-dihydroxyethyl aniline dissolved in 42mL of methanol-water mixed solvent in ice bath, reacting for 1.5h, adjusting the pH to 5-6 by using saturated sodium acetate, continuously stirring and reacting for 0.5h, performing suction filtration, washing with water, drying, and recrystallizing by using ethanol to obtain the azo compound B.
Fourthly, the compound B and the compound A are subjected to reflux reaction under the action of acetic acid and ammonium acetate to prepare a second-order nonlinear optical chromogenic molecule C containing tricyanofuran and dihydroxy groups, the second-order nonlinear optical chromophore C is a chromophore containing two hydroxyl groups and having a D-pi-A (electron donor-electron conjugated bridge-electron acceptor) structure, the electron donor of the second-order nonlinear optical chromophore molecule C is an electron donor of dihydroxy-containing aniline, the electron acceptor is an electron acceptor of a nitrobenzene or Tricyanofuran (TCF) or Tricyanopyrroline (TCP) structure, and the conjugated pi-electron bridge is a conjugated pi-electron bridge containing a benzene ring, a C-C double bond, an N-N double bond and one or more of thiophene, thiazole, pyrimidine, furan and benzothiazole aromatic heterocycles.
Specifically, in this embodiment: 0.6574g of compound A, 0.9401g of compound B, 0.03g of ammonium acetate, 0.05g of acetic acid and 40mL of ethanol are weighed, reflux reaction is carried out for 4h, the mixture is filtered while hot, washed by hot ethanol, filtrate is concentrated by distillation, filtered and dried to obtain a second-order nonlinear optical chromophore molecule C, and the chemical reaction equation is shown as formula (2):
synthesis of (di) fluorinated polyurethane imide electro-optic polymer
Dissolving a chromophore C and 4, 4' -diphenylmethane diisocyanate in a molar ratio of 1: 2.1-2.2 in N-methylpyrrolidone, reacting at 30-40 ℃ for 1-2h, reacting at 60-75 ℃ for 1-2h, reacting at 85-95 ℃ for 2-3h, cooling to room temperature, adding hexafluorodianhydride with the same molar weight as the chromophore or adding hexafluorodianhydride with the same molar weight as one half of the chromophore into the reaction liquid, reacting at 30-40 ℃ for 2-3h, reacting at 85-95 ℃ for 2-3h, reacting at 155-175 ℃ for 8-12h, cooling to room temperature, dropping the reaction liquid into methanol aqueous solution with the same volume ratio, performing suction filtration, drying at 60 ℃ to obtain a crude product, dissolving the crude product in N, N-dimethylformamide, and then dropping into methanol aqueous solution with the same volume ratio, and (4) carrying out suction filtration and drying at 60 ℃ to obtain the purified fluorinated polyurethane imide electro-optic waveguide material. The hexafluorodianhydride in this example was 4, 4' -hexafluoroisopropylidene phthalic anhydride. It should be noted that: the invention controls the structure of the polymer chain segment by setting the synthesis conditions.
Specifically, in this embodiment: dissolving 4.95g of chromophore C and 5.25g of 4,4 '-diphenylmethane diisocyanate in N-methylpyrrolidone, reacting for 1h at 40 ℃, reacting for 1h at 75 ℃, reacting for 2h at 90 ℃, cooling to room temperature, adding 4.44g of 4, 4' -hexafluoroisopropylidene phthalic anhydride into the reaction solution, reacting for 2h at 40 ℃, reacting for 2h at 90 ℃, reacting for 8h at 165 ℃, cooling to room temperature, adding the reaction solution into 100mL of methanol/100 mL of water, performing suction filtration, drying at 60 ℃ to obtain a crude product, dissolving the crude product in N, N-dimethylformamide, then adding the crude product into methanol aqueous solution with the same volume ratio, performing suction filtration, and drying at 60 ℃ to obtain the purified fluorinated polyurethane imide electro-optic waveguide material.
Example 2
The fluorinated polyurethane imide electro-optic waveguide material of this example is substantially the same as example 1, except that: in this example 4.95g of chromophoric molecule C and 5.25g of 4, 4' -diphenylmethane diisocyanate were dissolved in N-methylpyrrolidone, reacting at 40 ℃ for 1.5h, reacting at 75 ℃ for 1.5h, reacting at 90 ℃ for 2.5h, cooling to room temperature, adding 2.22g of 4, 4' -hexafluoroisopropylidene phthalic anhydride into the reaction solution, reacting at 40 ℃ for 2h, reacting at 90 ℃ for 2h, reacting at 165 ℃ for 9h, cooling to room temperature, adding hydroxyethyl methacrylate (0.03mol) into the reaction solution, reacting at 85 ℃ for 3h, cooling to room temperature, dropping the reaction solution into 100mL of methanol/100 mL of water, filtering, drying at 60 ℃ to obtain a crude product, dissolving the crude product in N, N-dimethylformamide, and then dripping the solution into methanol aqueous solution with the same volume ratio, carrying out suction filtration, and drying at 60 ℃ to obtain the purified crosslinkable fluorinated polyurethane imide electro-optic waveguide material. It should be noted that: the polymer synthesized in example 1 could not be crosslinked; in addition, in example 2, hydroxyethyl methacrylate (0.03mol) is added in the synthesis step to react for 3 hours at 85 ℃, so that the polymer synthesized in example 2 can be crosslinked, and the preparation process of the crosslinkable polymer in the processing of the polymer optical waveguide device can be simplified.
The fluorinated polyurethane imide prepared in the embodiment 1 or the embodiment 2 is used as a waveguide core layer material to prepare the MZ type polymer optical waveguide electro-optic modulator, and good electro-optic modulation response is obtained under a low-frequency modulation condition through an electro-optic modulation test, which indicates that the prepared fluorinated polyurethane imide is a better polymer electro-optic waveguide material and can be used for preparing a polymer optical waveguide electro-optic modulation device. The optical performance of the fluorinated polyurethane imide was tested, the refractive index at 1550nm was measured with a prism coupler to be 1.6258, the electro-optic coefficient γ 33 at 1550nm was measured with a simple reflection method to be 68 pm/V, and the optical transmission loss at 1550nm was measured with a waveguide cut-off method to be 1.78 dB/cm.
The above examples are only intended to illustrate the technical solution of the present invention and are not intended to be limiting. Although the present invention has been described in detail with reference to the preferred embodiments, it will be understood by those skilled in the art that various changes may be made and equivalents may be substituted without departing from the scope of the present invention.
Claims (4)
1. A fluorinated polyurethane imide electro-optic waveguide material is characterized in that: the fluorinated polyurethane imide electro-optic waveguide material is a polymer with a Y-shaped structure, wherein a nitrogen-containing hydroxyl group in a color-generating molecule forms one part of a polymer main chain, and an electron conjugate bridge and an electron acceptor part in the color-generating molecule are bonded to the polymer main chain as side chains.
2. The fluorinated polyurethane imide electro-optic waveguide material of claim 1, wherein the preparation comprises the following steps:
(1) synthesizing a compound A containing a tricyanofuran structure from 3-hydroxy-3-methyl-2-butanone and malononitrile according to a molar ratio of 1: 2.1-2.3 under the catalysis of sodium ethoxide;
(2) carrying out diazo salt reaction on the p-aminobenzaldehyde and sodium nitrite with sulfuric acid according to the molar ratio of 1: 1.1-1.2, and then carrying out coupling reaction on the diazo salt and N, N-dihydroxyethyl aniline with the same molar amount as the p-aminobenzaldehyde to prepare an azo compound B;
(3) carrying out reflux reaction on the compound B and the compound A under the action of acetic acid and ammonium acetate to prepare a second-order nonlinear optical chromogenic molecule C containing tricyanofuran and a dihydroxy group;
(4) dissolving a chromophore C and 4, 4' -diphenylmethane diisocyanate in a molar ratio of 1: 2.1-2.2 in N-methylpyrrolidone, reacting at 30-40 ℃ for 1-2h, reacting at 60-75 ℃ for 1-2h, reacting at 85-95 ℃ for 2-3h, cooling to room temperature, adding hexafluorodianhydride with the same molar weight as the chromophore or adding hexafluorodianhydride with the same molar weight as one half of the chromophore into the reaction liquid, reacting at 30-40 ℃ for 2-3h, reacting at 85-95 ℃ for 2-3h, reacting at 155-175 ℃ for 8-12h, cooling to room temperature, dropping the reaction liquid into methanol aqueous solution with the same volume ratio, performing suction filtration, drying at 60 ℃ to obtain a crude product, dissolving the crude product in N, N-dimethylformamide, and then dropping into methanol aqueous solution with the same volume ratio, and (4) carrying out suction filtration and drying at 60 ℃ to obtain the purified fluorinated polyurethane imide electro-optic waveguide material.
3. A fluorinated polyurethane imide electro-optic waveguide material as claimed in claim 2 wherein: the second-order nonlinear optical chromophore C is a chromophore having a D-pi-A (electron donor-electron conjugate bridge-electron acceptor) structure and containing two hydroxyl groups, the electron donor of the second-order nonlinear optical chromophore C is an aniline containing dihydroxy serving as an electron donor, the electron acceptor is an electron acceptor containing nitrobenzene or Tricyanofuran (TCF) or tricyano pyrroline (TCP) structure, and the conjugated pi electron bridge contains benzene rings, C-C double bonds, N-N double bonds and one or more aromatic heterocycles containing thiophene, thiazole, pyrimidine, furan and benzothiazole serving as a conjugated pi electron bridge.
4. A fluorinated polyurethane imide electro-optic waveguide material as claimed in claim 2 wherein: the hexafluoro dianhydride is 4, 4' -hexafluoroisopropylidene phthalic anhydride.
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Citations (4)
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|---|---|---|---|---|
| EP0791849A1 (en) * | 1996-02-26 | 1997-08-27 | ENICHEM S.p.A. | Non-linear optical compounds |
| US5811507A (en) * | 1993-10-21 | 1998-09-22 | Flamel Technologies | Polyesterimides for use in linear and/or non-linear optics, and one method for preparing same |
| CN101134805A (en) * | 2007-08-07 | 2008-03-05 | 江苏大学 | Method for preparing linear polyester-imides and thermal-optical property usage thereof |
| CN101246222A (en) * | 2007-12-07 | 2008-08-20 | 东南大学 | Fluorine-contained polyimide optical waveguide material and method for producing the same |
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2020
- 2020-08-01 CN CN202010763890.7A patent/CN111909378B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5811507A (en) * | 1993-10-21 | 1998-09-22 | Flamel Technologies | Polyesterimides for use in linear and/or non-linear optics, and one method for preparing same |
| EP0791849A1 (en) * | 1996-02-26 | 1997-08-27 | ENICHEM S.p.A. | Non-linear optical compounds |
| CN101134805A (en) * | 2007-08-07 | 2008-03-05 | 江苏大学 | Method for preparing linear polyester-imides and thermal-optical property usage thereof |
| CN101246222A (en) * | 2007-12-07 | 2008-08-20 | 东南大学 | Fluorine-contained polyimide optical waveguide material and method for producing the same |
Non-Patent Citations (3)
| Title |
|---|
| JAVIER PEREZ-MORENO ET AL.: ""Modulated Conjugation as a Means of Improving the Intrinsic Hyperpolarizability"", 《J. AM. CHEM. SOC.》 * |
| LONG-DE WANG ET AL.: ""Study on the synthesis and optical properties of polyurethane-imide"", 《6TH INTERNATIONAL SYMPOSIUM ON ADVANCED OPTICAL MANUFACTURING AND TESTING TECHNOLOGIES: ADVANCED OPTICAL MANUFACTURING TECHNOLOGIES》 * |
| LONG-DE WANG ET AL.: ""Synthesis and characterization of cross-linkable polyurethane-imide electro-optic waveguide polymer"", 《APPLIED PHYSICS A-MATERIALS SCIENCE & PROCESSING》 * |
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