CN105131974B - Phenanthridone-structure heterocyclic polymerizable liquid crystal compound and preparation method thereof - Google Patents
Phenanthridone-structure heterocyclic polymerizable liquid crystal compound and preparation method thereof Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 56
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 43
- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000012788 optical film Substances 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- RZFVLEJOHSLEFR-UHFFFAOYSA-N phenanthridone Chemical group C1=CC=C2C(O)=NC3=CC=CC=C3C2=C1 RZFVLEJOHSLEFR-UHFFFAOYSA-N 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229940126062 Compound A Drugs 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 239000010408 film Substances 0.000 abstract description 12
- 238000010438 heat treatment Methods 0.000 abstract 1
- -1 phenanthridone compound Chemical class 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 0 CN(c(ccc(C(O*)=O)c1)c1-c1ccccc11)C1=O Chemical compound CN(c(ccc(C(O*)=O)c1)c1-c1ccccc11)C1=O 0.000 description 4
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000005034 decoration Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000004088 simulation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The invention provides a phenanthridone-structure heterocyclic polymerizable liquid crystal compound shown in a general formula I. The phenanthridone compound has a high refractive index, can be cured under the action of heating or ultraviolet and visible light, does not yellow easily, has good film forming ability after curing, can be widely used in the fields of panel display, flexible display and other optical films.
Description
Technical Field
The invention relates to a polymerizable liquid crystal compound, a preparation method of the polymerizable liquid crystal compound and application of the polymerizable liquid crystal compound in an optical film.
Background
The polymerizable liquid crystal compound plays a positive role in the fields of specific optical films such as a naked-eye 3D Lenticular Lens film (lenticulars), an optical retardation film (Retard), a patterned retardation film (Pattern Retard) and the like because of its unique liquid fluidity and crystal order.
The retardation film can realize conversion among various polarization states, rotation of a polarization plane and modulation of various polarized lights, and has wide application in the fields of optical fiber communication, photoelastic, optical precision measurement, optical compensation of flat panel display and the like. In particular, the liquid crystal display device plays an increasingly important role in optical compensation of liquid crystal display. For example, for a passive matrix vertical alignment liquid crystal display, under the conditions of no electric field and oblique incidence of light, a certain phase delay is generated due to the existence of an included angle when incident light passes through a liquid crystal layer, at the moment, the phase delay caused by the oblique incidence can be effectively compensated by adopting a delay film, and oblique-view-angle light leakage is restrained, so that the visual angle characteristic of the liquid crystal display is improved. In addition, for color liquid crystal display, display is realized by modulating RGB three primary colors, not only the retardation is precisely controlled, but also the dispersion performance of the retardation film is strictly required, and the dispersion performance of the retardation film has a significant influence on color liquid crystal display.
As for the non-polymerizable liquid crystal with high refractive index, there have been many scientific researches, such as reviewed by Zhang Chiyong et al (research progress of high birefringent liquid crystal compound, liquid crystal and display, 2014,29, 873-. The central group is mainly composed of cyclic structures, such as benzene ring, naphthalene ring or cyclohexane, bridging groups can be introduced among the cyclic structures, and side groups can be introduced on the rings.
Wherein SL and SR are left and right groups, RL and RR are left and right cyclic groups, and M is a bridging group.
The who et al (molecular design and simulation calculation of fast high birefringence nematic liquid crystal, liquid crystal and display, 2009,24,15-21) provides a whole set of semi-empirical quantum chemical algorithms, and can obtain Δ n of liquid crystal material through simulation calculation.
In the non-liquid crystal domain, the high refractive index resin is usually added with inorganic compound and fluorine-containing group or sulfur-containing atom to improve the refractive index. However, inorganic compounds have adverse effects on liquid crystals in liquid crystals, and have a large odor during synthesis of sulfur atoms, which is not favorable for industrial production.
The refractive index of the conventional polymerizable liquid crystal is about 0.15. The existing high-refractive-index polymerizable liquid crystal contains acetylene bonds and cyano groups, and is easy to cause yellowing and high in viscosity. Therefore, there is a particular need for new polymerizable liquid crystals free of acetylenic and cyano groups that meet the needs of optical films.
Disclosure of Invention
The purpose of the invention is as follows: the invention aims to overcome the defects of the prior art and provide a heterocyclic ring-containing high-refractive-index polymerizable liquid crystal compound. Another object of the present invention is to provide a method for preparing a heterocyclic ring-containing polymerizable liquid crystal compound. It is still another object of the present invention to provide a use of the heterocyclic ring-containing polymerizable liquid crystal compound.
The technical scheme is as follows: in order to achieve the above object, the present invention provides a heterocyclic polymerizable liquid crystal compound having a phenanthridinone structure of the general formula i:
wherein,
R1is hydrogen or alkyl with 1-6 carbon atoms, or aromatic hydrocarbon which can be mono-or polysubstituted by methyl;
R2is hydrogen or methyl;
x is a single bond or carbonyl;
z is-COO-or-OCO-;
m is 0 or 1;
n is an integer of 1 to 11.
In some embodiments of the invention, the compound of formula I is selected from the group consisting of compounds of formula I-1:
wherein,
R1is hydrogen or alkyl with 1-6 carbon atoms;
R2is hydrogen or methyl;
x is a single bond or carbonyl;
m is 0 or 1;
n is an integer of 1 to 11.
In some embodiments of the invention, the compound of formula I is selected from the group consisting of compounds of formula I-2:
wherein,
R2is hydrogen or methyl;
n is an integer of 1 to 11.
In some preferred embodiments of the present invention, the compound of formula I-1 is selected from the group consisting of compounds of formulae I-1-1 to I-1-6:
and
in some preferred embodiments of the present invention, the compound of formula I-2 is selected from the group consisting of compounds of formulae I-2-1 to I-2-4:
and
the synthetic route of the general formula I-1 is shown as follows:
wherein R is1Is hydrogen or alkyl with 1-6 carbon atoms; r2Is hydrogen or methyl; x is a single bond or carbonyl; m is 0 or 1; n is an integer of 1 to 11.
Adding A and B in a certain molar ratio into a reaction vessel, simultaneously adding a corresponding polymerization inhibitor (such as hydroquinone), a catalyst (such as p-toluenesulfonic acid) and a solvent (such as benzene and substituted benzene solvents), performing reflux reaction to obtain a crude product I-1, and purifying by passing through a column to obtain a refined product I-1.
The synthetic route of the general formula I-2 is shown as follows:
wherein R is2Is hydrogen or methyl; n is an integer of 1 to 11.
Adding C and D in a certain molar ratio into a reaction container, simultaneously adding a corresponding polymerization inhibitor (such as hydroquinone), a catalyst (such as p-toluenesulfonic acid) and a solvent (such as benzene and substituted benzene solvents), performing reflux reaction to obtain a crude product I-2, and purifying by passing through a column to obtain a refined product I-2.
The invention also provides application of the compound with the general formula I in the fields of flat panel display, flexible display and functional optical films.
Detailed Description
The invention will be illustrated below with reference to specific embodiments. It should be noted that the following examples are illustrative of the present invention, and are not intended to limit the present invention.
The mother liquid crystal is selected from commercial liquid crystal with the serial number of TS023-102 produced by Jiangsu Hecheng display science and technology GmbH. The obtained compound was dissolved in a mother substance in a weight ratio of 20%, and n was adjusted by Abbe refractometeroAnd neThe measurements were made and △ n was calculated and the birefringence △ n (25 ℃, 589nm) of the polymerized liquid crystal composition was extrapolated in a linear relationship based on the ratio of the composition in the matrixoAnd neThe angle of the ocular needs to be adjusted, the difference between the two is 90 degrees, and △ n is equal to ne-no。
Example 1
1.1mmol of Compound A1 and 1mmol of Compound B1 were put in a 50mL round bottom flask, and 0.1mmol of hydroquinone, 1mmol of p-toluenesulfonic acid and 20mL of a toluene solution were added, followed by reflux reaction at 115 ℃ for 4 hours. The product was extracted with ethyl acetate and passed through a column to give 0.22 g of a pale yellow compound I-1-1.
1H NMR(CHCl3)：8.58(1H),8.50(1H),8.31(1H),8.15(1H),8.09(2H),7.80(1H),7.68(1H),7.56(1H),7.47(2H),6.36(1H),6.12(1H),5.97(1H),4.26(2H),4.09(2H),3.89(3H),1.80(2H),1.65(2H).
Compound I-1-1 was found to have Δ n ═ 0.25.
Example 2
1.1mmol of Compound A1 and 1mmol of Compound B2 were put in a 50mL round bottom flask, and 0.1mmol of hydroquinone, 1mmol of p-toluenesulfonic acid and 20mL of a toluene solution were added, followed by reflux reaction at 115 ℃ for 4 hours. The product was extracted with ethyl acetate and passed through a column to give 0.31 g of a pale yellow compound I-1-5.
1H NMR(CHCl3)：8.58(1H),8.49(1H),8.39(1H),8.15(1H),7.90(2H),7.79(1H),7.68(1H),7.55(1H),7.47(2H),6.38(1H),6.30(1H),4.17(2H),4.09(2H),3.89(3H),2.01(3H),1.77(2H),1.67(2H),1.48(2H),1.38(2H)。
Compound I-1-5 was found to have Δ n of 0.26.
Example 3
1.1mmol of Compound A2 and 1mmol of Compound B3 were put in a 50mL round bottom flask, and 0.1mmol of hydroquinone, 1mmol of p-toluenesulfonic acid and 20mL of a toluene solution were added, followed by reflux reaction at 115 ℃ for 4 hours. The product was extracted with ethyl acetate and passed through a column to give 0.32 g of a pale yellow compound I-1-6.
1H NMR(CHCl3)：8.52(2H),8.28(1H),8.10(1H),7.93(2H),7.81(1H),7.71(1H),7.52(1H),7.45(2H),6.33(1H),6.05(2H),4.74(1H),4.23(2H),4.09(1H),3.92(2H),1.65(4H),1.46(4H),1.22(3H)。
Compound I-1-6 was found to have Δ n of 0.25.
Example 4
1mmol of Compound A3 and 1.1mmol of Compound B4 were put in a 50mL round bottom flask, and 0.1mmol of hydroquinone, 1mmol of p-toluenesulfonic acid and 20mL of a toluene solution were added, followed by reflux reaction at 115 ℃ for 4 hours. The product was extracted with ethyl acetate and passed through a column to give 0.29 g of a pale yellow compound I-2-1.
1H NMR(CHCl3)：8.49(1H),8.25(1H),8.00(3H)7.68(1H),7.51(1H),7.27(1H),7.14(2H),7.09(1H),7.04(3H),6.36(1H),6.00(2H),4.10(4H),2.22(6H),1.92(2H),1.70(2H)。
Compound I-2-1 was found to have Δ n ═ 0.25.
Example 5
The polymerizable liquid crystal compounds I-1-1, I-1-5, I-1-6 and I-2-1 obtained in examples 1 to 4 were cured to obtain optical films which were not yellowed by sunlight irradiation for 10 days. The cured film has no pinhole defect and color stripe and has good film forming property.
The experiment results show that the heterocyclic polymerizable liquid crystal compound containing the phenanthridinone structure has high birefringence, and delta n is larger than 0.25. And the experimental result shows that the polymerizable liquid crystal compound provided by the invention is not easy to turn yellow, has long service life, can be used for preparing a film without pinhole defects and colored stripes, has good film forming property, can meet various requirements of optical films, and has a very good technical effect compared with the prior art.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (8)
1. A heterocyclic polymerizable liquid crystal compound having a phenanthridinone structure of formula I:
wherein,
R1is hydrogen or alkyl with 1-6 carbon atoms or phenyl substituted by methyl;
R2is hydrogen or methyl;
x is a single bond or carbonyl;
z is-COO-or-OCO-;
m is 0 or 1;
n is an integer of 1 to 11.
2. The heterocyclic polymerizable liquid crystal compound according to claim 1, wherein the compound is selected from the group consisting of compounds represented by general formula i-1:
wherein,
R1is hydrogen or alkyl with 1-6 carbon atoms;
R2is hydrogen or methyl;
x is a single bond or carbonyl;
m is 0 or 1;
n is an integer of 1 to 11.
3. The heterocyclic polymerizable liquid crystal compound according to claim 1, wherein the compound is selected from the group consisting of compounds represented by general formula i-2:
wherein,
R2is hydrogen or methyl;
n is an integer of 1 to 11.
4. The heterocyclic polymerizable liquid crystal compound according to claim 2, wherein the compound of the general formula i-1 is selected from the group consisting of compounds represented by general formulae i-1-1 to i-1-6:
5. the heterocyclic polymerizable liquid crystal compound according to claim 3, wherein the compound of the formula i-2 is selected from the group consisting of compounds represented by the formulae i-2-1 to i-2-4:
6. a method for preparing a heterocyclic polymerizable liquid crystal compound represented by the general formula I-1, which is characterized by comprising the following steps:
adding a compound A and a compound B in a certain molar ratio into a reaction vessel, simultaneously adding a corresponding polymerization inhibitor, a catalyst and a solvent, performing reflux reaction, and purifying by a column to obtain a refined compound of a general formula I-1:
wherein R is1Is hydrogen or alkyl with 1-6 carbon atoms; r2Is hydrogen or methyl; x is a single bond or carbonyl; m is 0 or 1; n is an integer of 1 to 11.
7. The preparation method of the heterocyclic polymerizable liquid crystal compound shown as the general formula I-2 is characterized by comprising the following steps:
adding compounds C and D in a certain molar ratio into a reaction vessel, simultaneously adding a corresponding polymerization inhibitor, a catalyst and a solvent, performing reflux reaction, and performing column purification to obtain a refined compound of a general formula I-2:
wherein R is2Is hydrogen or methyl; n is an integer of 1 to 11.
8. Use of the heterocyclic polymerizable liquid crystal compound according to any one of claims 1 to 5 for the production of flat panel displays, flexible displays and other optical films.
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| CN107082761B (en) * | 2017-04-17 | 2020-04-03 | 上海大学 | Phenanthridinone or benzophenanthridinone derivative and synthesis method thereof |
| JP7491660B2 (en) * | 2017-08-21 | 2024-05-28 | 住友化学株式会社 | Retardation plate with optical compensation function |
| KR102195455B1 (en) * | 2018-05-03 | 2020-12-28 | 주식회사 엘지화학 | Polymerizable liquid crystal compound, liquid crystal composition for optical element, polymer, optically anisotropic body, and optical element for display device |
| JP7279385B2 (en) * | 2019-02-07 | 2023-05-23 | 東ソー株式会社 | Polymerizable compounds, polymers and retardation films |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0946513B1 (en) * | 1996-12-19 | 2002-01-30 | Aventis Research & Technologies GmbH & Co. KG | Derivatives of 6-fluorophenanthridine for liquid crystal mixtures |
| CN102977017A (en) * | 2012-12-24 | 2013-03-20 | 湖南大学 | Method for catalytically preparing 6(5H)-phenanthridine ketone by copper component |
| CN103275003A (en) * | 2013-05-22 | 2013-09-04 | 浙江大学 | Method for preparing phenanthridinone derivative |
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| US6723733B2 (en) * | 2000-05-19 | 2004-04-20 | Guilford Pharmaceuticals, Inc. | Sulfonamide and carbamide derivatives of 6(5H)phenanthridinones and their uses |
| US6630254B2 (en) * | 2001-04-10 | 2003-10-07 | National Research Council Of Canada | Conjugated polycarbazole derivatives in Organic Light Emitting Diodes |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0946513B1 (en) * | 1996-12-19 | 2002-01-30 | Aventis Research & Technologies GmbH & Co. KG | Derivatives of 6-fluorophenanthridine for liquid crystal mixtures |
| CN102977017A (en) * | 2012-12-24 | 2013-03-20 | 湖南大学 | Method for catalytically preparing 6(5H)-phenanthridine ketone by copper component |
| CN103275003A (en) * | 2013-05-22 | 2013-09-04 | 浙江大学 | Method for preparing phenanthridinone derivative |
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