CN112961039A - Tripleeneyne compound and low-voltage PDLC (polymer dispersed liquid crystal) composition - Google Patents
Tripleeneyne compound and low-voltage PDLC (polymer dispersed liquid crystal) composition Download PDFInfo
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- CN112961039A CN112961039A CN202110192124.4A CN202110192124A CN112961039A CN 112961039 A CN112961039 A CN 112961039A CN 202110192124 A CN202110192124 A CN 202110192124A CN 112961039 A CN112961039 A CN 112961039A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/542—Macromolecular compounds
- C09K19/544—Macromolecular compounds as dispersing or encapsulating medium around the liquid crystal
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/90—Ring systems containing bridged rings containing more than four rings
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Abstract
The invention relates to a triptycene compound, which has a structural formula as follows:
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and relates to a triptycene compound and a low-voltage PDLC (polymer dispersed liquid crystal) composition.
Background
Polymer Dispersed Liquid Crystal (PDLC) is prepared by dispersing small microdroplets of Liquid Crystal in micron order in organic solid Polymer matrix, and because the optical axis of the microdroplets composed of Liquid Crystal molecules is in free orientation, the refractive index of the microdroplets is not matched with that of the matrix, and when light passes through the matrix, the microdroplets are scattered strongly to be in an opaque milky white state or a semitransparent state. Application of an electric field can adjust the optical axis orientation of the liquid crystal droplets, which when index matched, appear transparent. The electric field is removed and the liquid crystal droplets restore the original astigmatic state, thereby effecting a switching of the two states. The material with the electro-optic response characteristic is a membrane material with excellent comprehensive performance obtained by combining liquid crystal and polymer.
The PDLC material can be used for preparing products such as a dimming film, intelligent dimming glass, an electronic price tag, a display and the like, and has wide application in the fields of commercial space decoration, hotel decoration, office partition, projection display, optical modulators, thermosensitive and pressure-sensitive devices, electric control glass, light valves and electronic books at present.
The PDLC has many important parameters including photoelectric response curve, transmittance, driving voltage, adhesive force, service life and the like, wherein the driving voltage is an important parameter, and the driving voltage of the PDLC product commercialized by the PDLC at the present stage is generally above 60V and cannot reach below the safe voltage, so that certain potential safety hazard exists when the PDLC is used for bathroom partitions, glass curtain walls and other purposes, and the application range of the PDLC product is limited.
Disclosure of Invention
The invention aims to provide a triptycene compound and a low-voltage PDLC (polymer dispersed liquid crystal) composition, aims to overcome the defects of the prior art, and provides the triptycene compound, which has the advantages of simple synthesis steps, high yield and lower cost, can obviously reduce the driving voltage of a PDLC (polymer dispersed liquid crystal) after being used for a PDLC formula, can not generate yellowing phenomenon after being placed outdoors for a long time after being prepared into a PDLC product, and has higher popularization and application values.
The invention is realized by the following technical scheme:
a tripropenylalkyne compound has a structural formula as follows:
wherein R isAAre the same or different and are each independently represented by R1-(Z1-A1-Z2)x-；
RBIs represented by R2-(Z3-A2-Z4)y-；
Wherein R is1And R2And each independently is selected from-H, -D, -T, -Cl, -F, -CN, -CD3、-CF3、-OCF3Any one of-COOH, an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 15 carbon atoms, a linear alkenyl group having 2 to 15 carbon atoms, a fluorinated alkyl group having 1 to 15 carbon atoms, a fluorinated alkoxy group having 1 to 15 carbon atoms, or a fluorinated linear alkenyl group having 2 to 15 carbon atoms;
Z1、Z2、Z3and Z4Each independently selected from-O-, -S-, -OCO-, -COO-, -CO-, -CH2O-、 -OCH2-、-OCF2-, at least one or none of a linear alkyl group having 1 to 15 carbon atoms, a linear alkenyl group having 2 to 15 carbon atoms, a linear alkynyl group having 2 to 15 carbon atoms, a fluorinated linear alkyl group having 1 to 15 carbon atoms, a fluorinated alkenyl group having 2 to 15 carbon atoms, or a carbon-carbon single bond;
A1and A2Each independently selected from 1, 4-cyclohexylene, 1, 4-phenylene, diphenylphosphino, N-phenyl-carbazol-2-yl, N-phenyl-carbazol-3-one or none of a group, a 9, 10-anthracenyl group, a 1-naphthyl group, a 2-naphthyl group, a 4-triphenylamino group, a 2, 5-pyrimidyl group, a 3, 9-carbazolyl group, a 2, 5-pyridyl group, a 2, 5-tetrahydro-2H-pyranyl group, a 1, 3-dioxane-2, 5-yl group, a 1,2, 4-oxadiazol-3, 5-yl group, a fluorinated 1, 4-cyclohexylene group, a fluorinated pyran ring diyl group, a cyclic lactone diyl group, a five-membered oxaheterocycle diyl group, a five-membered thiazacyclo diyl group, a five-membered azacyclo diyl group or a carbon-carbon single bond;
x and y each independently represent an integer of 0 to 3.
Further, when x or y is 2 or 3, the structural unit Z1-A1-Z2In, Z1Identical or different, A1Same or different, Z2The same or different; structural unit Z3-A2-Z4In, Z3Identical or different, A2Same or different, Z4The same or different.
A low-voltage PDLC liquid crystal composition comprises a photocuring material, a liquid crystal material, a photoinitiator, a spacer, a phosphorus-containing additive and a triptycene compound in any one of the materials;
the light curing material accounts for 30-60% of the total weight of the PDLC, the liquid crystal material accounts for 65-35% of the total weight of the PDLC, the photoinitiator accounts for 0.1-5% of the total weight of the PDLC, the spacer accounts for 1-3 per mill of the total weight of the PDLC, and the phosphorus-containing additive accounts for 1-3 per mill of the total weight of the PDLC; the triptycene compound accounts for 1% -5% of the total weight of the PDLC.
Further, the light-cured material is a light-cured prepolymer and a diluent.
Further, the light-cured prepolymer is one or more of acrylic polyurethane, acrylic polyarylate, organic silicon prepolymer or epoxy prepolymer.
The diluent is hydroxypropyl acrylate, hydroxypropyl methacrylate, lauryl acrylate, lauryl methacrylate, 3-chloro-2-hydroxy-methacrylate, isobornyl acrylate, isobornyl methacrylate, 1, 6-hexanediol diacrylate, ethoxylated trimethylolpropane triacrylate, ethylphenoxy acrylate, ethylphenoxy methacrylate, 3, 5-trimethylcyclohexyl acrylate, propane trimethanol triacrylate, trimethylolpropane tri (3-mercaptopropionate), benzyl acrylate, benzyl methacrylate, hexyl acrylate, hexyl methacrylate, dicyclopentenyl acrylate, dicyclopentenyl methacrylate, ethylene glycol dimethacrylate, glycidyl methacrylate, glycidyl acrylate, lauryl methacrylate, 3-chloro-2-hydroxy-methacrylate, isobornyl acrylate, isobornyl methacrylate, 1, 6-hexanediol diacrylate, ethoxylated trimethylolpropane triacrylate, ethylphenoxy methacrylate, 3, 5-trimethylcyclohexyl acrylate, trimethylolpropane trimethacrylate, benzyl acrylate, benzyl methacrylate, hexyl acrylate, dicyclopentenyl methacrylate, ethylene, 2, 2, 2-trifluoroethyl acrylate, tetrahydrofurfuryl methacrylate, 2-hydroxyethyl acrylate, 2-ethyl acrylate monomer, 2, 2, 2-trifluoroethyl methacrylate, acetoacetic acid ethylene glycol methacrylate, cyclohexane acrylate, cyclohexane methacrylate or dodecyl acrylate.
Further, the liquid crystal material is a commercially available liquid crystal mixture.
Further, the photoinitiator is one or more of organic peroxide initiator, inorganic peroxide initiator, azo initiator or redox initiator.
Further, the spacers are rigid microbeads with the same diameter between 10 and 40 microns and are used for controlling the distance uniformity between the two substrates of the light modulation film.
Further, the phosphorus-containing additive comprises phosphorus-containing acrylate and phosphate.
The invention has the beneficial effects that:
compared with the commercial mature PDLC product, the PDLC mixed crystal of the compound has the following advantages:
the PDLC is applied to a dimming film or dimming glass, and compared with a mature PDLC product at the present stage, the driving voltage is reduced by 20-40V, so that the driving voltage is reduced to a safe voltage, the bonding force is strong, the photoelectric characteristic is excellent, the PDLC product cannot be yellowed after being placed outdoors for a long time after being made, the application range of the PDLC product is greatly expanded, and the PDLC has important application value.
Detailed Description
The technical solutions of the present invention are described in detail below by examples, and the following examples are only exemplary and can be used only for explaining and explaining the technical solutions of the present invention, but not construed as limiting the technical solutions of the present invention.
In the following examples of the present application, unless otherwise specified, reagents, materials and the like used in the present application are commercially available.
EXAMPLE 1 preparation of Compound Comp01
Into a 100mL two-necked flask, 167mg (0.50mmol) of Comp01a, 73mg (0.50mmol) of Comp01b, 7mg (0.01mmol) of Pd (PPh)3)2Cl2，2mg(0.01mmol)CuI，276mg (2.00mmol)K2CO350mL of tetrahydrofuran, refluxing for 8h, draining the solvent, performing alumina column chromatography, and performing petroleum ether: elution with dichloromethane ═ 1:2 gave 166mg of a yellow solid in 83% yield.
EXAMPLE 2 preparation of Compound Comp02
Into a 100mL two-necked flask, 188mg (0.50mmol) of Comp02a, 143mg (0.50mmol) of Comp02b, 7mg (0.01mmol) of Pd (PPh)3)2Cl2，2mg(0.01mmol)CuI，276 mg(2.00mmol)K2CO350mL of tetrahydrofuran, refluxing for 8h, draining the solvent, performing alumina column chromatography, and performing petroleum ether: elution with dichloromethane ═ 1:2 gave 264mg of a yellow solid in 91% yield.
Example 3
The PDLC Liq1 comprises 12% of acrylic polyurethane CN704 (Saedoma), 23% of hydroxypropyl acrylate, 64.9% of liquid crystal material SL-79 (Chengzonghua display materials Co., Ltd.), 0.1% of photoinitiator UV184, 1% of spacer (10um) and 1% of phosphorus-containing additive glyceric acid dimethacrylate.
The PDLC Liq2 comprises the following components, Liq1 accounts for 99%, and Comp01 accounts for 1%.
Example 4
The PDLC Liq3 comprises 14% of acrylic polyurethane CN966J75NS (Saedoma), 24% of lauryl acrylate, 61.5% of liquid crystal material SLC1717 (Chengzonghua display materials, Inc.), 0.5% of photoinitiator UV184, 2% of spacer (15um) and 2% of phosphorus-containing additive acryloyloxyethyl phenyl phosphate.
The PDLC Liq4 comprises the following components, Liq3 accounts for 97.5%, and Comp1 accounts for 2.5%.
Example 5
The PDLC Liq5 comprises the following components of 28% of polyarylate acrylate CN975 (Saedoma), 12% of lauryl acrylate, 2% of 2, 2, 2-trifluoroethyl methacrylate, 2% of cyclohexane acrylate, 7% of hydroxypropyl acrylate, 47.5% of liquid crystal material I71-004 (Chengzonghua display materials, Inc.), 2.5% of photoinitiator ITX, 3% of spacer (30um) and 3% of phosphorus-containing additive methacryloxy thiophosphate derivative.
The PDLC Liq6 comprises the following components, Liq5 accounts for 97%, and Comp02 accounts for 3%.
Example 6
The PDLC Liq7 comprises 28% of epoxy prepolymer, 11% of lauryl acrylate, 8% of 1, 6-hexanediol diacrylate, 5% of ethoxylated trimethylolpropane triacrylate, 10% of hydroxypropyl acrylate, 35% of liquid crystal material SL-79 (Chengzonghua display materials Co., Ltd.), 3% of photoinitiator lauroyl peroxide, 2% of spacer (40um) and 3% of phosphorus-containing additive-based acryloyloxy thiophosphate derivative.
The PDLC Liq8 comprises the following components, Liq7 accounts for 95.5%, and Comp2 accounts for 4.5%.
EXAMPLE 7 preparation of PDLC light-adjusting Film-1-8
1) Spreading the base material on a coating table, setting the speed of a coating machine to be 20mm/s, respectively dripping the PDLC Liq1-Liq8 prepared in the above examples 3-6 on a coating head of a scraper, and starting a start button to coat;
2) placing the membrane in an ultraviolet curing machine with the dosage of 0.5-2.5 mW/cm2Curing for 2min to obtain the Film-1-Film-8 of PDLC.
PDLC dimming film performance detection conditions:
transmittance, drive voltage: WGT-S transmittance/haze tester.
The performance test results of the PDLC dimming Film membranes Film-1 to Film-8 are shown in Table 1, and Film-9 is the product performance of the market.
TABLE 1 Film-1 to Film-9 Performance test results
Therefore, after the prepared triptycene compound is introduced into a PDLC formula, the driving voltage of the prepared PDLC product can be obviously reduced, and the on-state transmittance and the off-state haze are basically consistent with those of the original product, so that the use voltage can be reduced to be within a safe voltage range. Due to the acetylene structure introduced into the system, a certain polymer network structure can be formed in the system under the illumination of UV, and the rapid rotation of liquid crystal molecules is promoted, so that the effect of reducing the voltage of the system is achieved. Compared with the conventional PDLC light modulation film product on the market, the PDLC light modulation film prepared by the invention has obviously lower driving voltage, equivalent optical performance and obviously better applicability, and the effect cannot be expected by the technical personnel in the field.
EXAMPLE 8 yellowing Properties of PDLC Film-1 Film-8
Since the common product containing acetylene compounds gradually yellows under the condition of UV light, thereby affecting the appearance performance of the product, the yellowing performance test is carried out on the Film-1-Film-8 prepared in example 7.
Placing the membrane in an ultraviolet curing machine with the concentration of 2.0mW/cm2The energy irradiation for 48h finds that the appearances of Film2, Film4, Film6 and Film8 do not show any change compared with Film1, Film3, Film5 and Film7 respectively, which shows that the triptycene compound added in the invention can obviously reduce the driving voltage of a PDLC product, and does not generate the problem of yellowing after UV is introduced, because the large steric hindrance group of the triptycene increases the stability of alkyne molecules under UV light, compared with the formula before the triptycene compound is introduced, the triptycene compound does not generate the problem of yellowing, and the compound has obviously better applicability, and the effect cannot be expected by technicians in the field.
Although the present invention has been described in connection with the preferred embodiments, it is not limited to the above-described embodiments, and it is to be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the present invention, and the scope of the present invention is outlined by the appended claims.
Claims (9)
1. A triptycene compound is characterized in that the structural formula is as follows:
RBIs represented by R2-(Z3-A2-Z4)y-；
Wherein R is1And R2And each independently is selected from-H, -D, -T, -Cl, -F, -CN, -CD3、-CF3、-OCF3COOH, an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 15 carbon atoms, a linear alkenyl group having 2 to 15 carbon atoms, a fluorinated alkyl group having 1 to 15 carbon atoms, a fluorinated alkoxy group having 1 to 15 carbon atoms, or a fluorinated orthocarbon groupAny one of linear alkylene groups with the sub-number of 2-15;
Z1、Z2、Z3and Z4Each independently selected from-O-, -S-, -OCO-, -COO-, -CO-, -CH2O-、-OCH2-、-OCF2-, at least one or none of a linear alkyl group having 1 to 15 carbon atoms, a linear alkenyl group having 2 to 15 carbon atoms, a linear alkynyl group having 2 to 15 carbon atoms, a fluorinated linear alkyl group having 1 to 15 carbon atoms, a fluorinated alkenyl group having 2 to 15 carbon atoms, or a carbon-carbon single bond;
A1and A2Independently of one another, from the group consisting of 1, 4-cyclohexylene, 1, 4-phenylene, diphenylphosphinyl, N-phenyl-carbazol-2-yl, N-phenyl-carbazol-3-yl, 9, 10-anthracenyl, 1-naphthyl, 2-naphthyl, 4-triphenylamino, 2, 5-pyrimidinyl, 3, 9-carbazolyl, one or none of 2, 5-pyridyl, 2, 5-tetrahydro-2H-pyranyl, 1, 3-dioxane-2, 5-yl, 1,2, 4-oxadiazol-3, 5-yl, fluorinated 1, 4-cyclohexylene, fluorinated pyran ring diyl, cyclic lactone diyl, five-membered oxaheterocyclic diyl, five-membered thiaheterocyclic diyl, five-membered azaheterocyclic diyl or a carbon-carbon single bond;
x and y each independently represent an integer of 0 to 3.
2. The triple-cycloalkyne compound according to claim 1, wherein the structural unit Z is Z when x or y is 2 or 31-A1-Z2In, Z1Identical or different, A1Same or different, Z2The same or different; structural unit Z3-A2-Z4In, Z3Identical or different, A2Same or different, Z4The same or different.
3. A low voltage PDLC liquid crystal composition comprising a photocurable material, a liquid crystal material, a photoinitiator, a spacer, a phosphorus-containing additive and a tripropenylene alkyne compound as claimed in any one of claims 1 or 2;
the light curing material accounts for 30-60% of the total weight of the PDLC, the liquid crystal material accounts for 65-35% of the total weight of the PDLC, the photoinitiator accounts for 0.1-5% of the total weight of the PDLC, the spacer accounts for 1-3 per mill of the total weight of the PDLC, and the phosphorus-containing additive accounts for 1-3 per mill of the total weight of the PDLC; the triptycene compound accounts for 1% -5% of the total weight of the PDLC.
4. The low voltage PDLC liquid crystal composition of claim 3, wherein said photo-curable material is a photo-curable prepolymer and a diluent.
5. The low voltage PDLC composition according to claim 4, wherein said photo-curable prepolymer is one or a combination of more than one of acrylic polyurethane, acrylic polyarylate, silicone prepolymer or epoxy prepolymer;
the diluent is hydroxypropyl acrylate, hydroxypropyl methacrylate, lauryl acrylate, lauryl methacrylate, 3-chloro-2-hydroxy-methacrylate, isobornyl acrylate, isobornyl methacrylate, 1, 6-hexanediol diacrylate, ethoxylated trimethylolpropane triacrylate, ethylphenoxy acrylate, ethylphenoxy methacrylate, 3, 5-trimethylcyclohexyl acrylate, propane trimethanol triacrylate, trimethylolpropane tri (3-mercaptopropionate), benzyl acrylate, benzyl methacrylate, hexyl acrylate, hexyl methacrylate, dicyclopentenyl acrylate, dicyclopentenyl methacrylate, ethylene glycol dimethacrylate, glycidyl methacrylate, glycidyl acrylate, lauryl methacrylate, 3-chloro-2-hydroxy-methacrylate, isobornyl acrylate, isobornyl methacrylate, 1, 6-hexanediol diacrylate, ethoxylated trimethylolpropane triacrylate, ethylphenoxy methacrylate, 3, 5-trimethylcyclohexyl acrylate, trimethylolpropane trimethacrylate, benzyl acrylate, benzyl methacrylate, hexyl acrylate, dicyclopentenyl methacrylate, ethylene, 2, 2, 2-trifluoroethyl acrylate, tetrahydrofurfuryl methacrylate, 2-hydroxyethyl acrylate, 2-ethyl acrylate monomer, 2, 2, 2-trifluoroethyl methacrylate, acetoacetic acid ethylene glycol methacrylate, cyclohexane acrylate, cyclohexane methacrylate or dodecyl acrylate.
6. The low voltage PDLC liquid crystal composition of claim 3, wherein said liquid crystal material is a commercially available liquid crystal mixture.
7. The low voltage PDLC composition according to claim 3, wherein said photoinitiator is one or more of organic peroxide initiator, inorganic peroxide initiator, azo initiator or redox initiator.
8. The low voltage PDLC liquid crystal composition of claim 3, wherein said spacer is a rigid bead with a diameter between 10 μm and 40 μm, and is used to control the distance uniformity between two substrates of light modulating film.
9. The low voltage PDLC liquid crystal composition of claim 3, wherein said phosphorus-containing additives comprise phosphorus-containing acrylates and phosphates.
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| WO2020230756A1 (en) * | 2019-05-13 | 2020-11-19 | 学校法人立教学院 | Metal-organic structural body |
| WO2021018383A1 (en) * | 2019-07-30 | 2021-02-04 | Transitions Optical, Ltd. | Mesogen compounds |
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2021
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| CN103373892A (en) * | 2012-04-25 | 2013-10-30 | 华中科技大学 | Three-dimensional nanometer graphene based on triptycene and preparation method thereof |
| CN104956490A (en) * | 2013-02-12 | 2015-09-30 | 国立研究开发法人科学技术振兴机构 | Electronic device using organic thin film, and electronic apparatus containing same |
| JP2018180219A (en) * | 2017-04-11 | 2018-11-15 | 富士フイルム株式会社 | Laminate, alignment layer for forming composition, and alignment layer |
| WO2020230756A1 (en) * | 2019-05-13 | 2020-11-19 | 学校法人立教学院 | Metal-organic structural body |
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