CN104327090B - Volution disc liquid-crystal compounds and preparation method and application - Google Patents

Volution disc liquid-crystal compounds and preparation method and application Download PDF

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CN104327090B
CN104327090B CN201410541127.4A CN201410541127A CN104327090B CN 104327090 B CN104327090 B CN 104327090B CN 201410541127 A CN201410541127 A CN 201410541127A CN 104327090 B CN104327090 B CN 104327090B
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CN104327090A (en
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郭剑
李正强
张兴
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
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    • G02B5/305—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid comprising multiple thin layers, e.g. multilayer stacks including organic materials, e.g. polymeric layers
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Abstract

The invention discloses a kind of volution disc liquid-crystal compounds and preparation method and application.The volution disc liquid-crystal compounds, its general structure is shown in formula I.Compound shown in the Formulas I, nuclear-magnetism detection is correct, studies less based on TN types optical compensation films at this stage, discotic mesogenic material category used is less, and synthesis technique is complex, it is difficult to the problems such as withdrawing deposit, this patent provides a series of volution disc liquid-crystal compounds using novel microwave synthesis method.Such compound, and raw material is easy to get, prepares easy, and overall yield is high, for progress and the application of studying optical compensation membrane material, with important application value.

Description

Volution disc liquid-crystal compounds and preparation method and application
Technical field
The invention belongs to technical field of organic synthesis, it is related to a kind of volution disc liquid-crystal compounds and preparation method thereof and answers With.
Background technology
All the time, in liquid crystal display device (LCD) due to have from tilted direction observe when contrast reduction or tone Change, therefore viewing angle characteristic is compared with CRT and insufficient, there is considerable room for improvement.The main cause of viewing angle characteristic of LCD In the dependence of angle of the birefringence of liquid crystal molecule.For example, twisted nematic mode (TN) liquid crystal display device is due to corresponding speed Degree and contrast are excellent, and productivity ratio is also high, therefore as the display hand of the various devices such as the OA equipment such as PC or monitor Section and widely popularize.But, in the liquid crystal display device of above-mentioned TN patterns, because liquid crystal molecule is relative to upper and lower electrode Substrate tilted alignment, therefore exist that angle according to the observation is different, the contrast of display image changes, because of picture coloring And cause the problem of the view angle dependency increase such as reduction that visibility occurs.Therefore need two-fold to this with optical compensation films Penetrating property, the dependence of angle for postponing compensate to improve viewing angle characteristic.
In order to improve to viewing angle characteristic, discotic liquid-crystalline molecules are used in the liquid crystal display device of above-mentioned TN patterns And optical compensation films are obtained by polymerization.But, although the disc liquid-crystal compounds for reporting many types in the prior art are used In optical compensation membrane material, but all exist that some are complicated including synthetic method, yield is relatively low, and dissolubility is poor, it is difficult to preserve Shortcoming.Therefore, synthesis step is simple, and high income, the discotic liquid-crystalline molecules with unique photoelectric characteristic turn into important at this stage Research contents.
The content of the invention
To solve above-mentioned technical problem present in prior art, the present inventor carries by further investigation and complicated experiment A kind of volution disc liquid-crystal compounds and preparation method and application are supplied.
The present invention provide volution disc liquid-crystal compounds, its general structure shown in formula I,
In the Formulas I, RAIt is R1-(Z1-A1-Z2)x-；
RBIt is-(Z3-A2-Z4)y-R2；
Wherein, R1、R2Independently selected from H ,-F ,-Cl ,-CN ,-CF3With-OCF3, the total number of carbon atoms for 1-15 alkyl, carbon Total atom number is the alkoxy of 1-15, the total number of carbon atoms is the linear alkene base of 2-15, the total number of carbon atoms of fluoro is 1-15's Alkyl, fluoro the total number of carbon atoms for 1-15 alkoxy and fluoro the total number of carbon atoms for 2-15 linear alkene base in appoint Meaning is a kind of；
Z1、Z2、Z3And Z4Independently selected from-O- ,-S- ,-OCO- ,-COO- ,-CO- ,-CH2O-、-OCH2-、-CF2O-、- OCF2-, the total number of carbon atoms be the straight chained alkyl of 1-15, the total number of carbon atoms be the linear alkene base of 2-15, the total number of carbon atoms be 2- 15 straight-chain alkynyl, the total number of carbon atoms of fluoro are the straight chained alkyl of 1-15, the total number of carbon atoms of fluoro is the alkylene of 2-15 With at least one in carbon-carbon single bond；
A1And A2Independently selected from 1,4- cyclohexylidenes, 1,4- phenylenes, two phenenyl phosphinyl, N- phenyl-carbazole -2- bases, N- phenyl-carbazole -3- bases, 9,10- anthryls, 1- naphthyls, 4- triphenylamine bases, 2,5- pyrimidine radicals, 3,9- carbazyls, 2,5- pyridines Base, 2,5- tetrahydrochysene -2H- pyranoses, 1,3- diox -2,5- bases, 1,2,4- oxadiazole -3,5- bases, the 1,4- Asias hexamethylene of fluoro Base, the 1,4- phenylenes of fluoro, the pyranoid ring diyl of fluoro, cyclic lactone diyl, five yuan of oxa- ring diyls, pentatomic sulphur heterocycles two Any one in base, penta azacyclo diyl and carbon-carbon single bond；
X and y independently are the integer of 0-3；
When the x or y independently are 2 or 3, construction unit Z1-A1-Z2In, Z1Identical or different, the A when occurring every time1 Identical or different, Z when occurring every time2It is identical or different when occurring every time；Construction unit Z3-A2-Z4In, Z3When occurring every time It is identical or different, A2Identical or different, the Z when occurring every time4It is identical or different when occurring every time.
Compound shown in the Formulas I is also compound obtained by being prepared as follows.
The method for preparing the compound of formula I that the present invention is provided, comprises the following steps：
1) alkynes shown in catechol and Formula II is carried out into cyclization under conditions of ruthenium is catalyst, is reacted Compound shown in formula III is obtained after finishing；
2) by compound shown in formula III under conditions of ferric trichloride is catalyst, microwave carries out cyclization, has reacted Compound shown in Formulas I is obtained after finishing；
The reaction equation of compound method is as follows shown in above-mentioned formula I：
The step of above method 1) in, catechol is 1 with the mol ratio of Formula II compound:1~1.5, concretely 1: 1.0、1:1.1、1:1.2、1:1.3、1:1.4、1:1.5, preferably 1:1.1；Catechol is 1 with the mol ratio of ruthenium:0.1~ 1.0, concretely 1:0.1、1:0.2、1:0.3、1:0.4、1:0.5、1:0.6、1:0.7、1:0.8、1:0.9、1:1.0, preferably 1:0.2；In the reactions steps, cyclization temperature be 0 DEG C~100 DEG C, concretely 0 DEG C~-20 DEG C, 20 DEG C~40 DEG C, 40 DEG C~60 DEG C, 60 DEG C~80 DEG C, 80 DEG C~100 DEG C, preferably 80 DEG C~100 DEG C；Reaction time is 2~12 hours, preferably 6 ~8 hours；
The step of above method 2) in, formula III compound is 1 with the mol ratio of ferric trichloride:1~5, concretely 1: 1.0、1:2.0、1:3.0、1:4.0、1:5.0, preferably 1:3.0；In the reactions steps, cyclization temperature is 0 DEG C~100 DEG C, concretely 0 DEG C~-20 DEG C, 20 DEG C~40 DEG C, 40 DEG C~60 DEG C, 60 DEG C~80 DEG C, 80 DEG C~100 DEG C, preferably 20 DEG C~ 40℃；Reaction time is 1~30 minute, preferably 1~10 minute；
The step 1) and step 2) carry out in a solvent；
The solvent is chosen in particular from tetrahydrofuran, hexane, dichloromethane, acetic acid, dimethylbenzene, ethanol, toluene, water, adjacent two At least one in chlorobenzene, acetic acid and 1,4- dioxane；
The step 1) and step 2) in, reaction atmosphere is inert atmosphere, preferably argon gas atmosphere.
Application of the compound in optical compensation membrane material shown in the Formulas I that the invention described above is provided and prepare organic electroluminescence Luminescent device material, organic solar battery material and the application prepared in Organic Light Emitting Diode fall within protection of the invention Scope.
The compound that the present invention is provided, nuclear-magnetism detection is correct, studies less based on TN types optical compensation films at this stage, used Discotic mesogenic material category is less, and synthesis technique is complex, it is difficult to the problems such as withdrawing deposit, and this patent is closed using novel microwave A series of volution disc liquid-crystal compounds are provided into method.Such compound is compared with existing similar compound, and raw material is easy , simplicity is prepared, overall yield is high, for progress and the application of studying optical compensation membrane material, with important application value, Achieve unexpected technique effect.
Specific embodiment
With reference to specific embodiment, the present invention is further elaborated, but the present invention is not limited to following examples.Institute State method and be conventional method unless otherwise instructed.The raw material can be obtained from open commercial sources unless otherwise instructed.
Embodiment 1, compoundPreparation
Step 1：Synthesis
To 500mL round-bottomed bottles, catechol, the ruthenium of the 1b and 2mmol of 11.0mmol of 10.0mmol are put into, added 200mL dichloromethane, 80 DEG C of reaction 8h.System is spin-dried for obtaining yellow liquid.Silicagel column is crossed, yellow liquid is obtained with petroleum ether drip washing Body product, yield：44%.
Step 2：Synthesis
To 100mL microwave reactors, the FeCl of 1b, 9.0mmol of 3.0mmol is put into3With the dichloromethane of 40mL, 500w Lower 30 DEG C of reactions 5min.System is poured into the 200mL aqueous solution, is stirred 10 minutes.Liquid, water is divided mutually to be extracted with 15mL dichloromethane Three times, organic phase washing is spin-dried for obtaining yellow liquid after merging.Silicagel column is crossed, yellow solid product is obtained with ethyl acetate drip washing, Yield：48%.
1H NMR(CDCl3,300MHz):δ=7.92 (s, 6H), 2.09-2.06 (m, 6H), 1.76 (s, 9H), 0.91 (t, 9H).
13C NMR(CDCl3,75MHz):δ=143.4,122.0,112.4,110.3,34.2,25.8,9.7.
From the foregoing, it will be observed that the white solid product structure is correct, it is compound shown in Formulas I
Embodiment 2, compoundSynthesis
Step 1：Synthesis
The step 1 of this step reference implementation example 1,2a is replaced with by the 1a of the step 1 of embodiment 1, and other operations of other conditions are same The step 1 of embodiment 1, yield 44%.
Step 2：Synthesis
The step 2 of this step reference implementation example 1,2b is replaced with by the 1b of the step 2 of embodiment 1, and other operations of other conditions are same The step 2 of embodiment 1, yield：48%.
1H NMR(CDCl3,300MHz):δ=7.94 (s, 6H), 2.09-2.06 (m, 6H), 1.76 (s, 9H), 1.31- 1.29(m,6H),0.91(t,9H).
13C NMR(CDCl3,75MHz):δ=142.6,122.0,112.4,110.3,43.4,34.2,26.1,15.5, 14.7.
From the foregoing, it will be observed that the white solid product structure is correct, it is compound shown in Formulas I
Embodiment 3, compoundSynthesis
Step 1：Synthesis
The step 1 of this step reference implementation example 1,3a is replaced with by the 1a of the step 1 of embodiment 1, and other operations of other conditions are same The step 1 of embodiment 1, yield 58%.
Step 2：Synthesis
The step 2 of this step reference implementation example 1,3b is replaced with by the 1b of the step 2 of embodiment 1, and other operations of other conditions are same The step 2 of embodiment 1, yield：56%.
1H NMR(CDCl3,300MHz):δ=7.94 (s, 6H), 2.09-2.06 (m, 12H), 1.31-1.29 (m, 18H), 0.91(t,18H).
13C NMR(CDCl3,75MHz):δ=142.6,122.0,113.6,110.3,41.1,38.6,23.3,19.7, 15.8,14.7,14.1.
From the foregoing, it will be observed that the white solid product structure is correct, it is compound shown in Formulas I
Embodiment 4, compoundSynthesis
Step 1：Synthesis
The step 1 of this step reference implementation example 1,4a is replaced with by the 1a of the step 1 of embodiment 1, and other operations of other conditions are same The step 1 of embodiment 1, yield 34%.
Step 2：Synthesis
The step 2 of this step reference implementation example 1,4b is replaced with by the 1b of the step 2 of embodiment 1, and other operations of other conditions are same The step 2 of embodiment 1, yield：43%.
1H NMR(CDCl3,300MHz):δ=7.92 (s, 6H), 7.40-7.38 (m, 6H), 7.79-7.27 (m, 9H), 3.31(s,6H),1.76(s,9H).
13C NMR(CDCl3,75MHz):δ=143.4,138.0,128.8,128.1,126.0,122.0,112.3, 110.3,46.4,25.7.
From the foregoing, it will be observed that the white solid product structure is correct, it is compound shown in Formulas I
Embodiment 5, compoundSynthesis
Step 1：Synthesis
The step 1 of this step reference implementation example 1,5a is replaced with by the 1a of the step 1 of embodiment 1, and other operations of other conditions are same The step 1 of embodiment 1, yield 46%.
Step 2：Synthesis
The step 2 of this step reference implementation example 1,5b is replaced with by the 1b of the step 2 of embodiment 1, and other operations of other conditions are same The step 2 of embodiment 1, yield：43%.
1H NMR(CDCl3,300MHz):δ=7.92 (s, 6H), 7.40-7.29 (m, 30H), 3.64 (s, 9H)
13C NMR(CDCl3,75MHz):δ=143.6,141.1,139.4,128.9,128.6,127.7,127.6, 126.1,125.9,122.0,121.0,110.3,49.5.
From the foregoing, it will be observed that the white solid product structure is correct, it is compound shown in Formulas I
Embodiment 6, compoundSynthesis
Step 1：Synthesis
The step 1 of this step reference implementation example 1,6a is replaced with by the 1a of the step 1 of embodiment 1, and other operations of other conditions are same The step 1 of embodiment 1, yield 26%.
Step 2：Synthesis
The step 2 of this step reference implementation example 1,6b is replaced with by the 1b of the step 2 of embodiment 1, and other operations of other conditions are same The step 2 of embodiment 1, yield：64%.
1H NMR(CDCl3,300MHz):δ=7.92 (s, 6H), 2.05 (t, 12H), 1.31-1.29 (m, 78H), 0.88 (t,18H).
13C NMR(CDCl3,75MHz):δ=143.4,122.0,113.9,110.3,38.9,31.9,30.2,29.6, 29.3,23.3,22.7,14.1.
From the foregoing, it will be observed that the white solid product structure is correct, it is compound shown in Formulas I
Embodiment 7, compoundSynthesis
Step 1：Synthesis
The step 1 of this step reference implementation example 1,7a is replaced with by the 1a of the step 1 of embodiment 1, and other operations of other conditions are same The step 1 of embodiment 1, yield 38%.
Step 2：Synthesis
The step 2 of this step reference implementation example 1,7b is replaced with by the 1b of the step 2 of embodiment 1, and other operations of other conditions are same The step 2 of embodiment 1, yield：44%.
1H NMR(CDCl3,300MHz):δ=7.92 (s, 6H), 7.38-7.36 (m, 15H), 7.25 (d, 6H), 7.02 (d, 6H),3.64(s,12H),2.75-2.72(m,6H),1.86(t,12H),1.61-1.31(m,39H),0.90(t,9H).
13C NMR(CDCl3,75MHz):δ=144.2,143.4,141.1,136.6,128.9,127.6,127.4, 126.4,126.0,122.0,121.0,110.3,49.5,43.7,37.1,31.1,31.0,29.3,20.5,14.4.
From the foregoing, it will be observed that the white solid product structure is correct, it is compound shown in Formulas I
Embodiment 8, compound's Synthesis
Step 1：Synthesis
The step 1 of this step reference implementation example 1,87a is replaced with by the 1a of the step 1 of embodiment 1, and other operations of other conditions are same The step 1 of embodiment 1, yield 33%.
Step 2：Synthesis
The step 2 of this step reference implementation example 1,8b is replaced with by the 1b of the step 2 of embodiment 1, and other operations of other conditions are same The step 2 of embodiment 1, yield：31%.
1H NMR(CDCl3,300MHz):δ=7.92 (s, 6H), 7.42-7.35 (m, 24H), 7.25 (d, 6H), 7.02 (d, 6H),3.64(s,6H),2.74-2.72(m,3H),2.62(t,6H),1.86-1.31(m,45H),0.90(t,9H).
13C NMR(CDCl3,75MHz):δ=144.2,143.4,140.9,140.0,139.7,138.1,136.6, 131.0,130.0,128.7,127.6,127.4,126.4,122.1,121.4,110.3,49.5,43.7,37.9,37.1, 31.1,31.0,29.3,24.1,20.1,14.3,13.8.
From the foregoing, it will be observed that the white solid product structure is correct, it is compound shown in Formulas I
Embodiment 9 prepares optical compensation films diaphragm Film-1~Film-8
1) by 2min in the NaOH solution of TAC (80 μm) base material immersion 1.5mol/L, 5min then is rinsed with clear water, then soak Enter the H of 0.05mol/L2SO42min is neutralized in solution, with clear water rinse 5min, finally flowing air in 100 DEG C enter Row dries 5min；
2) weigh 0.2g polyvinyl alcohol (PVA) to be put into vial, add 3.6g deionized waters, be placed on magnetic stirring apparatus 70 DEG C are stirred 8 hours, add 1.2g methanol solvates and 0.01g glutaraldehyde solutions, stir 30min；
3) base material is laid on coating cloth deck, knife type coater thickness is set to 0.1mm, speed is set to 20mm/s, will The above-mentioned coating fluid for 2) preparing is dropped at scraper for coating head, starts start button, is coated；
4) wet film is placed in drying box 60 DEG C and dries 60s, then 90 DEG C dry 150s；
5) print of drying and forming-film is placed on rubbing machine, opens vavuum pump button, sample held, by rubbing machine thickness Scale is set to 1 lattice, comes and goes 5 times, carries out friction matching；
6) weigh discotic mesogenic 1-8 obtained by 0.5g embodiments to be put into vial, add 2g butanone solvents, carry out molten Solution, stirs 1 hour, adds 0.005g light triggers 184, stirs 30min；
7) 5) it is placed on above-mentioned on coating cloth deck with the sample become better, knife type coater thickness is set to 0.06mm, speed sets 20mm/s is set to, the above-mentioned coating fluid for 6) preparing is dropped at scraper for coating head, start start button, be coated；
8) wet film is placed in drying box 130 DEG C and dries 2min, be then placed in uv curing machine using 50mW/cm2's Energy-curable 5min.Obtain the optical compensation films of optical anisotropic layer/oriented layer/TAC base material three-deckers.
Optical compensation films performance detection condition：
Transmitance：Tested using Shimadzu UV-2450 visible spectrophotometers；
Length of delay：LCT-5016C type liquid crystal comprehensive parameter testers；
Thickness：Tested using thousand points of THICKNESS GAUGE FOR THE MEASUREMENT OF THIN FOILSs of CH-1-st.
The performance test results of the gained optical compensation films diaphragm Film-1 to Film-8 of embodiment 9 are as shown in table 1.
The performance test results of table 1, Film-1 to Film-8
From the foregoing, it will be observed that the optical compensation films that the discotic liquid-crystalline molecules containing heterocycle structure of the invention are fabricated to, transmitance It is high, with certain compensation effect.The conventional optical compensation being fabricated to the existing discotic liquid-crystalline molecules containing heterocycle structure Film, the transmitance of optical compensation films of the invention is much higher, with the compensation effect for becoming apparent.Such effect is this area What technical staff to be expected.
Although with reference to preferred embodiment, the present invention is described, the invention is not limited in above-described embodiment, should Work as understanding, under the guiding of present inventive concept, those skilled in the art can carry out various modifications and improvements, and appended claims are general The scope of the present invention is included.

Claims (8)

1. compound shown in Formulas I：
In the Formulas I, RAIt is R1-(Z1-A1-Z2)x-；
RBIt is-(Z3-A2-Z4)y-R2；
Wherein, R1、R2Alkyl, the alcoxyl that the total number of carbon atoms is 1-15 independently selected from H ,-F ,-Cl, the total number of carbon atoms for 1-15 Base, fluoro the total number of carbon atoms for 1-15 alkyl and fluoro the total number of carbon atoms for 1-15 alkoxy in any one；
Z1、Z2、Z3And Z4Independently selected from the straight chained alkyl, the total number of carbon atoms of fluoro that the total number of carbon atoms is 1-15 for 1-15's is straight At least one in alkyl group and carbon-carbon single bond；
A1Independently selected from 1,4- cyclohexylidenes, 1,4- phenylenes, the 1,4- cyclohexylidenes of fluoro, the 1,4- phenylenes of fluoro and Any one in carbon-carbon single bond；
A2Any one in 1,4- phenylenes, the 1,4- cyclohexylidenes of fluoro, the 1,4- phenylenes of fluoro；
X is the integer of 0-3；
Y is the integer of 1-3；
When the x or y independently are 2 or 3, construction unit Z1-A1-Z2In, Z1Identical or different, the A when occurring every time1Each It is identical or different during appearance, Z2It is identical or different when occurring every time；Construction unit Z3-A2-Z4In, Z3It is identical when occurring every time Or different, A2Identical or different, the Z when occurring every time4It is identical or different when occurring every time.
2. a kind of method for preparing compound shown in Formulas I described in claim 1, comprises the following steps：
1) alkynes shown in catechol and Formula II is carried out into cyclization under conditions of ruthenium is catalyst, reaction is finished After obtain compound shown in formula III；
2) by substituted heterocyclic compound shown in formula III under conditions of ferric trichloride is catalyst, microwave carries out cyclization, instead Compound shown in Formulas I is obtained after should finishing.
3. method according to claim 2, it is characterised in that：The step 1) in, catechol and Formula II compound Mol ratio is 1:1~1.5；Catechol is 1 with the mol ratio of ruthenium:0.1~1.0；
The step 2) in, formula III compound is 1 with the mol ratio of ferric trichloride:1~5.
4. method according to claim 3, it is characterised in that：The step 2) in, formula III compound and ferric trichloride Mol ratio is 1:1.0、1:2.0、1:3.0、1:4.0 or 1:5.0.
5. the method according to any one of claim 2-4, it is characterised in that：
The step 1) in, cyclization temperature is 0 DEG C~100 DEG C；Reaction time is 2~12 hours；
The step 2) in, cyclization temperature is 0 DEG C~100 DEG C；Reaction time is 1~30 minute；
The step 1) and step 2) carry out in a solvent；
The solvent be chosen in particular from tetrahydrofuran, hexane, dichloromethane, acetic acid, dimethylbenzene, ethanol, toluene, water, o-dichlorohenzene, At least one in acetic acid and 1,4- dioxane；
The step 1) and step 2) in, reaction atmosphere is inert atmosphere.
6. method according to claim 5, it is characterised in that：
The step 1) in, cyclization temperature is 80 DEG C~100 DEG C；Reaction time is 6~8 hours；
The step 2) in, cyclization temperature is 20 DEG C~40 DEG C；Reaction time is 1~10 minute；
The reaction atmosphere is argon gas atmosphere.
7. application of the compound in optical compensation membrane material shown in Formulas I described in claim 1.
8. the optical compensation membrane material of compound shown in Formulas I described in claim 1 is contained.
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