CN101768055A - Liquid crystal compound and preparation method thereof - Google Patents
Liquid crystal compound and preparation method thereof Download PDFInfo
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- CN101768055A CN101768055A CN 201010034350 CN201010034350A CN101768055A CN 101768055 A CN101768055 A CN 101768055A CN 201010034350 CN201010034350 CN 201010034350 CN 201010034350 A CN201010034350 A CN 201010034350A CN 101768055 A CN101768055 A CN 101768055A
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- alkyl
- biphenyl
- acetylene
- compound
- iodo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 47
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- ZWLHKPCYGMMCFY-UHFFFAOYSA-N 1-iodoanthracene Chemical class C1=CC=C2C=C3C(I)=CC=CC3=CC2=C1 ZWLHKPCYGMMCFY-UHFFFAOYSA-N 0.000 claims description 19
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 10
- 239000012298 atmosphere Substances 0.000 claims description 6
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000012769 display material Substances 0.000 claims description 3
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 abstract description 27
- 239000000463 material Substances 0.000 abstract description 6
- 239000000178 monomer Substances 0.000 abstract description 2
- 241001597008 Nomeidae Species 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 229960001866 silicon dioxide Drugs 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 238000004811 liquid chromatography Methods 0.000 description 6
- 238000000967 suction filtration Methods 0.000 description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000003381 solubilizing effect Effects 0.000 description 2
- 150000001454 anthracenes Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Abstract
The invention discloses a liquid crystal compound and a preparation method thereof. The provided liquid crystal compound is provided with a U molecular structure and is a derivant of anthracene, and a structural general formula is shown in formula I, wherein R1, R2 or R3 stands for alkyl (C1 to C15). The provided preparation method for the liquid crystal compound includes the following steps: under the catalytic action of Pd (Ph3P) 2C12 and CuI, coupling reaction is carried out between 4-alkyl biphenyl-4-acetylene or trans-4`-(4`` alkyl cyclohexyl) biphenyl-4` ``-acetylene and 9-alkoxy iodide anthracene, so as to obtain a target product. With the U-type molecular structure and high-definition bright spots, the provided liquid crystal compound can be used as a liquid crystal material; with a large conjugated system, the compound can be used as a luminescent material for an OLED. Moreover, with a liquid crystal phase, the material can be used as a liquid crystal monomer. (Formula I).
Description
Technical field
The present invention relates to a kind of liquid crystalline cpd and preparation method thereof.
Background technology
Along with the continuous development of technology and people to the improving constantly of display requirement, flat pannel display has demonstrated its superior performance and progressively move towards and lived, and becomes the main trend of current technique of display.Plasma display, liquid-crystal display, display of organic electroluminescence are three big main flows of present flat panel display.Wherein, liquid-crystal display has the long advantage of low power consumption, life-span, and display of organic electroluminescence has from advantages such as main light emission, wide visual angle, color are abundant.
Summary of the invention
The objective of the invention is a kind of liquid crystalline cpd and preparation method thereof.
The liquid crystalline cpd that provides of the present invention has " U " molecular structure, is the derivative of anthracene, and its general structure is suc as formula shown in the I,
(formula I)
In the described formula I general structure, R
1Be the alkyl of C1-C15, R
2For the alkyl of C1-C15 or
Wherein, R
3Alkyl for C1-C15.
Work as R
2For
The time, this structural general formula is suc as formula shown in the II,
(formula II)
Above-mentioned liquid crystalline cpd specifically can be any one in following each compound:
4,5-two (4 '-alkyl biphenyl-4 " ethynyl)-the 9-alkoxy anthracene
Two kinds of methods that prepare compound shown in the above-mentioned formula I general structure provided by the invention, method one comprises the steps: the (Ph at Pd
3P)
2Cl
2And under the katalysis of CuI, 4-alkyl biphenyl-4-acetylene and 9-alkoxyl group two iodo anthracenes are carried out linked reaction, obtain compound shown in the described formula I general structure.
The synthetic route of liquid crystalline cpd is as follows shown in the above-mentioned formula I general structure:
In the aforesaid method, the mol ratio of 4-alkyl biphenyl-4-acetylene and 9-alkoxyl group two iodo anthracenes is 2-3: 1, specifically can be 2-2.4: 1,2-2.45: 1,2.25-2.45: 1 or 2.45-2.5: 1, preferred 2.25～2.5: 1; Temperature of reaction is the reflux temperature of reaction system, as 80-150 ℃, specifically can be 80-100 ℃, 80 ℃, 100 ℃, 150 ℃, 100-150 ℃, 90 ℃, 110 ℃, 120 ℃, 130 ℃, 140 ℃, 110-150 ℃ or 120-140 ℃, reaction times is 12-48 hour, reaction atmosphere is an inert atmosphere, preferred nitrogen atmosphere.Pd (Ph
3P)
2Cl
2The consumption that reaches CuI is the 1-15% of 9-alkoxyl group two iodo anthracene mole dosage, specifically can be 1-10%, 2-10%, 5-10%, 2-15%, 10-15%, 1-6% or 3-4%, preferred 2～5%.Described organic solvent is selected from least a in triethylamine and the toluene, and as long as its consumption is can the solubilizing reaction thing.Also add the promotor triphenylphosphine in this reaction system, the consumption of described triphenylphosphine is catalyst P d (Ph
3P)
2Cl
2The 16-20 of quality doubly, specifically can be 16 times, 16.7 times, 20 times, 16-18 doubly or 16.7-20 doubly.
The method of compound shown in the above-mentioned formula I general structure of preparation provided by the invention, method two comprises the steps: the (Ph at Pd
3P)
2Cl
2And under the katalysis of CuI, with trans-4 '-(4 " alkyl-cyclohexyl) biphenyl-4 " '-acetylene and 9-alkoxyl group two iodo anthracenes carry out linked reaction, obtain compound shown in the described formula I general structure.
The synthetic route of liquid crystalline cpd is as follows shown in the above-mentioned formula I general structure:
In the aforesaid method, described trans-4 '-(4 " alkyl-cyclohexyl) biphenyl-4 " '-alkyl in the acetylene is preferably amyl group.Trans-4 '-(4 " alkyl-cyclohexyl) biphenyl-4 " '-mol ratio of acetylene 4-alkyl biphenyl-4-acetylene and 9-alkoxyl group two iodo anthracenes is 2-3: 1, specifically can be 2-2.57: 1,2-2.6: 1,2.25-2.6: 1 or 2.5-2.6: 1, preferred 2.25～2.5: 1; Temperature of reaction is the reflux temperature of reaction system, as 80-150 ℃, specifically can be 80-100 ℃, 80 ℃, 100 ℃, 150 ℃, 100-150 ℃, 90 ℃, 110 ℃, 120 ℃, 130 ℃, 140 ℃, 110-150 ℃ or 120-140 ℃, reaction times is 12-48 hour, reaction atmosphere is an inert atmosphere, preferred nitrogen atmosphere.Pd (Ph
3P)
2Cl
2The consumption that reaches CuI is the 1-15% of 9-alkoxyl group two iodo anthracene mole dosage, specifically can be 1-10%, 2-10%, 5-10%, 2-15%, 10-15%, 1-6% or 3-4%, preferred 2～5%.Described organic solvent is selected from least a in triethylamine and the toluene, and as long as its consumption is can the solubilizing reaction thing.Also add the promotor triphenylphosphine in this reaction system, the consumption of described triphenylphosphine is catalyst P d (Ph
3P)
2Cl
2The 16-20 of quality doubly, specifically can be 16 times, 16.7 times, 20 times, 16-18 doubly or 16.7-20 doubly.
In addition, the application of liquid crystalline cpd shown in the formula I general structure provided by the invention in preparation liquid crystal display material or Organic Light Emitting Diode (OLED) material also belongs to protection scope of the present invention.
Liquid crystalline cpd provided by the invention, nuclear-magnetism and IR detection architecture are correct, have " U " type molecular structure, are different from the linear bar-shaped of general liquid crystal molecule or encircle discous structure more; This compound has high clearing point simultaneously, can be used as liquid crystal display material; Because this compound has bigger conjugated system, can be used as the luminescent material of OLED.This material also has mesomorphic phase, can be used as liquid crystal monomer and uses.
Embodiment
The invention will be further described below in conjunction with specific embodiment, but the present invention is not limited to following examples.
Embodiment 1, compound 4,5-two (4 '-butyl biphenyl-4 " ethynyl)-preparation of 9-methoxyl group anthracene
With compound 4-butyl-biphenyl-4-acetylene 2g (8.5mmol), compound 9-methoxyl group two iodo anthracene A1.6g (3.5mmol), 0.5g triphenylphosphine, 0.3g Pd (Ph
3P)
2Cl
2Reach 0.2g CuI and join in the 100ml there-necked flask, add 35ml triethylamine and 20ml toluene again.Stirring and refluxing is 24 hours under nitrogen protection.Reaction solution gradually becomes the muddy liquid of Vandyke brown by yellow muddiness, and silica-gel plate launches to judge reaction end.Reaction finishes, and the suction filtration reaction solution obtains orange-yellow or pale brown look solid.Use CHCl
3Cross silicagel column, revolve and desolventize,, obtain the glassy yellow solid, be compound 4 with a large amount of ethyl acetate crystallizations, 5-two (4 '-butyl biphenyl-4 " ethynyl)-9-methoxyl group anthracene.Liquid chromatography purity is 99%, and yield is 65%.
DSC：Cr?242.65℃N254.45℃I；
IR：3060，2924，2854，2202，1599，1497，1350，1136，814，742。As can be known, this compound structure is correct.
Embodiment 2, compound 4,5-two (4 '-butyl biphenyl-4 " ethynyl)-preparation of 9-methoxyl group anthracene
With compound 4-butyl-biphenyl-4-acetylene 1.64g (7.0mmol), compound 9-methoxyl group two iodo anthracene A1.6g (3.5mmol), 0.5g triphenylphosphine, 0.3g Pd (Ph
3P)
2Cl
2And 0.2g CuI joins in the 100ml there-necked flask adding 35ml triethylamine and 20ml toluene.Stirring and refluxing is 24 hours under nitrogen protection.Reaction solution gradually becomes the muddy liquid of Vandyke brown by yellow muddiness, and silica-gel plate launches to judge reaction end.Reaction finishes, and the suction filtration reaction solution obtains orange-yellow or pale brown look solid.Use CHCl
3Cross silicagel column, revolve and desolventize,, obtain the glassy yellow solid, be compound 4 with a large amount of ethyl acetate crystallizations, 5-two (4 '-butyl biphenyl-4 " ethynyl)-9-methoxyl group anthracene.Liquid chromatography purity is 98.5%, and yield is 55%.
IR：3060，2920，2848，2202，1913，1599，1497，1350，1136，820，741。As can be known, this compound structure is correct.
Embodiment 3, compound 4,5-two (4 '-butyl biphenyl-4 " ethynyl)-preparation of 9-methoxyl group anthracene
With compound 4-butyl-biphenyl-4-acetylene 2g (8.5mmol), compound 9-methoxyl group two iodo anthracene A1.6g (3.5mmol), 0.5g triphenylphosphine, 0.025g Pd (Ph
3P)
2Cl
2And 0.02g CuI joins in the 100ml there-necked flask adding 35ml triethylamine and 20ml toluene.Stirring and refluxing is 24 hours under nitrogen protection.Reaction solution gradually becomes the muddy liquid of Vandyke brown by yellow muddiness, and silica-gel plate launches to judge reaction end.Reaction finishes, and the suction filtration reaction solution obtains orange-yellow or pale brown look solid.Use CHCl
3Cross silicagel column, revolve and desolventize,, obtain the glassy yellow solid, be compound 4 with a large amount of ethyl acetate crystallizations, 5-two (4 '-butyl biphenyl-4 " ethynyl)-9-methoxyl group anthracene.Liquid chromatography purity is 98.5%, and yield is 45%.
IR：3060，2920，2848，2202，1913，1599，1497，1350，1136，820，741。As can be known, this compound structure is correct.
Embodiment 4, compound 4,5-two (4 '-butyl biphenyl-4 " ethynyl)-preparation of 9-methoxyl group anthracene
With compound 4-butyl-biphenyl-4-acetylene 2g (8.5mmol), compound 9-methoxyl group two iodo anthracene A1.6g (3.5mmol), 0.5g triphenylphosphine, 0.3g Pd (Ph
3P)
2Cl
2And 0.2g CuI joins in the 100ml there-necked flask adding 35ml triethylamine and 20ml benzene, stirring and refluxing under nitrogen protection (80 ℃) 36 hours.Stirring and refluxing is 24 hours under nitrogen protection.Reaction solution gradually becomes the muddy liquid of Vandyke brown by yellow muddiness, and silica-gel plate launches to judge reaction end.Reaction finishes, and the suction filtration reaction solution obtains orange-yellow or pale brown look solid.Use CHCl
3Cross silicagel column, revolve and desolventize,, obtain the glassy yellow solid, be compound 4 with a large amount of ethyl acetate crystallizations, 5-two (4 '-butyl biphenyl-4 " ethynyl)-9-methoxyl group anthracene.Liquid chromatography purity is 98.5%, and yield is 62%.
IR：3060，2920，2848，2202，1913，1599，1497，1350，1136，820，741。As can be known, this compound structure is correct.
Embodiment 5, compound 4,5-two [trans-4 '-(4 " amyl group cyclohexyl) biphenyl-4 " '-ethynyl)-preparation of 9-methoxyl group anthracene
With compound trans-4 '-(4 " amyl group cyclohexyl) biphenyl-4 " '-acetylene 3g (9.0mmol), compound 9-methoxyl group two iodo anthracene A1.6g (3.5mmol), 0.5g triphenylphosphine, 0.3gPd (Ph
3P)
2Cl
2And 0.2g CuI joins in the 100ml there-necked flask adding 35ml triethylamine and 20ml toluene.Stirring and refluxing is 36 hours under nitrogen protection.Reaction solution gradually becomes the muddy liquid of Vandyke brown by yellow muddiness, and silica-gel plate launches to judge reaction end.Reaction finishes, and the suction filtration reaction solution obtains orange-yellow or pale brown look solid.Use CHCl
3Cross silicagel column, revolve and desolventize,, obtain the glassy yellow solid, be compound 4 with a large amount of ethyl acetate crystallizations, 5-two (4 '-butyl biphenyl-4 " ethynyl)-9-methoxyl group anthracene.Liquid chromatography purity is 98.5%, and yield is 59%.
DSC：Cr?287.5℃N(＞300℃)I；
IR：3060，2920，2848，2202，1913，1599，1497，1350，1136，820，741。As can be known, this compound structure is correct.
Embodiment 6, compound 4,5-two [trans-4 '-(4 " amyl group cyclohexyl) biphenyl-4 " '-ethynyl)-preparation of 9-methoxyl group anthracene
With compound trans-4 '-(4 " amyl group cyclohexyl) biphenyl-4 " '-acetylene 3g (9.0mmol), compound 9-methoxyl group two iodo anthracene A1.6g (3.5mmol), 0.35gPd (Ph
3P)
2Cl
2And 0.2g CuI joins in the 100ml there-necked flask adding 35ml triethylamine and 20ml toluene.Stirring and refluxing is 42 hours under nitrogen protection.Reaction solution gradually becomes the muddy liquid of Vandyke brown by yellow muddiness, and silica-gel plate launches to judge reaction end.Reaction finishes, and the suction filtration reaction solution obtains orange-yellow or pale brown look solid.Use CHCl
3Cross silicagel column, revolve and desolventize,, obtain the glassy yellow solid, be compound 4 with a large amount of ethyl acetate crystallizations, 5-two (4 '-butyl biphenyl-4 " ethynyl)-9-methoxyl group anthracene.Liquid chromatography purity is 98.8%, and yield is 55%.
DSC：Cr?287.5℃N(＞300℃)I；
IR：3060，2920，2848，2202，1913，1599，1497，1350，1136，820，741。As can be known, this compound structure is correct.
Claims (10)
1. liquid crystalline cpd shown in the formula I general structure,
(formula I)
In the described formula I general structure, R
1Be the alkyl of C1-C15, R
2For the alkyl of C1-C15 or
R
3Alkyl for C1-C15.
2. a method for preparing the described compound of claim 1 comprises the steps: the (Ph at Pd
3P)
2Cl
2And under the katalysis of CuI, with 9-alkoxyl group two iodo anthracenes in organic solvent with following compound in any one: 4-alkyl biphenyl-4-acetylene or trans-4 '-(4 " alkyl-cyclohexyl) biphenyl-4 " '-acetylene, carry out linked reaction, obtain the described compound of claim 1.
3. method according to claim 2 is characterized in that: the alkyl in described 4-alkyl biphenyl-4-acetylene and the 9-alkoxyl group two iodo anthracenes all is selected from the alkyl of C1-C15, preferred butyl; Described trans-4 '-(4 " alkyl-cyclohexyl) biphenyl-4 " '-alkyl in the acetylene is an amyl group.
4. according to claim 2 or 3 described methods, it is characterized in that: the mol ratio of described 4-alkyl biphenyl-4-acetylene and 9-alkoxyl group two iodo anthracenes is 2～3: 1; Described trans-4 '-(4 " alkyl-cyclohexyl) biphenyl-4 " '-mol ratio of acetylene 4-alkyl biphenyl-4-acetylene and 9-alkoxyl group two iodo anthracenes is 2～3: 1.
5. method according to claim 4, it is characterized in that: the mol ratio of described 4-alkyl biphenyl-4-acetylene and 9-alkoxyl group two iodo anthracenes is 2.25～2.5: 1, described trans-4 '-(4 " alkyl-cyclohexyl) biphenyl-4 " '-mol ratio of acetylene 4-alkyl biphenyl-4-acetylene and 9-alkoxyl group two iodo anthracenes is 2.25～2.5: 1.
6. according to the arbitrary described method of claim 2-5, it is characterized in that: in the described linked reaction, temperature is 80-150 ℃, and the time is 12-48 hour, and reaction atmosphere is an inert atmosphere, preferred nitrogen atmosphere; Described organic solvent is selected from least a in triethylamine and the toluene.
7. according to the arbitrary described method of claim 2-5, it is characterized in that: described Pd (Ph
3P)
2Cl
2The consumption that reaches CuI is the 1-15% of 9-alkoxyl group two iodo anthracene mole dosage, preferred 2～5%.
8. according to the arbitrary described method of claim 2-7, it is characterized in that: also add triphenylphosphine in the described linked reaction system.
9. method according to claim 8 is characterized in that: the consumption of described triphenylphosphine is catalyst P d (Ph
3P)
2Cl
2The 16-20 of quality doubly.
10. the application of the described compound of claim 1 in preparation liquid crystal display material or Organic Light Emitting Diode.
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| DE602004011615T2 (en) * | 2003-07-10 | 2009-01-29 | Merck Patent Gmbh | SUBSTITUTED ANTHRACENE |
| CN100391923C (en) * | 2005-10-17 | 2008-06-04 | 清华大学 | Alkylcyclohexyl multiple-fluorine biphenyl derivative and its preparation method and uses |
| CN101544892B (en) * | 2009-05-07 | 2012-10-03 | 石家庄诚志永华显示材料有限公司 | Method for synthesizing diaryl acetylene monomer liquid crystal |
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