CN100335591C - Organic electroluminescence liquid crystal compound, and its preparing method and use - Google Patents
Organic electroluminescence liquid crystal compound, and its preparing method and use Download PDFInfo
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- CN100335591C CN100335591C CNB2005101277972A CN200510127797A CN100335591C CN 100335591 C CN100335591 C CN 100335591C CN B2005101277972 A CNB2005101277972 A CN B2005101277972A CN 200510127797 A CN200510127797 A CN 200510127797A CN 100335591 C CN100335591 C CN 100335591C
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Abstract
The present invention discloses an organic electric light emitting liquid crystal compound and a preparing method and application thereof. The organic electric light emitting liquid crystal compound provided by the present invention has a structure as a formula I, wherein R is alkyl with a carbon atom number of 1 to 15. The compound of the present invention is novel blue organic electroluminescent material. Both solution and a solid film have strong fluorescence. The present invention is the ramification of anthracene has good thermal stability and high resolution performance. In addition, the present invention can also be used as liquid crystal display material and has wide application prospects.
Description
Technical field
The present invention relates to a kind of organic electroluminescence liquid crystal compound and preparation method thereof and application.
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 purpose of this invention is to provide a kind of electroluminescent organic material that both can produce blue light, can be used as compound of liquid crystal display material and preparation method thereof again.
Organic electroluminescence liquid crystal compound provided by the present invention, structure be suc as formula I,
(formula I)
Wherein, R is that carbonatoms is the alkyl of 1-15.
Here, R is preferably amyl group.
The preparation method of organic electroluminescence liquid crystal compound of the present invention comprises the steps:
1) earlier with formula II structure the alkyl-cyclohexyl bromobenzene is prepared as Grignard reagent, again with trimethyl borate B (OCH
3)
3Reaction, generating structure such as formula III to the alkyl-cyclohexyl phenylo boric acid after the hydrolysis;
(formula II) (formula III)
Wherein, R is that carbonatoms is the alkyl of 1-15;
2) will be to 9 of alkyl-cyclohexyl phenylo boric acid and formula IV structure, the 10-dibromoanthracene is at (Ph
3P)
4Pd catalysis is reaction down, obtains described organic electroluminescence liquid crystal compound.
Wherein, step 2) temperature of reaction is 100-200 ℃, and reaction solvent can be selected THF, N-Methyl pyrrolidone for use.
Another object of the present invention provides the purposes of The compounds of this invention.
Organic electroluminescence liquid crystal compound of the present invention has good solubility and stability, and can send blue light fluorescence, can be used as the luminescent material in the electroluminescent device, can be used to prepare electroluminescent device.In addition, organic electroluminescence liquid crystal compound of the present invention also has mesomorphic phase, can also use as liquid crystal monomer simultaneously, can be used to prepare liquid crystal display material.
The compounds of this invention is a kind of novel blue organic electroluminescent material, all has stronger fluorescence in solution and solid film; It is the derivative of anthracene, has good thermostability and high resolution, and can be used as the liquid crystal display material use, has a extensive future.
Description of drawings
Fig. 1 is 9, the nuclear magnetic resonance spectrum of 10-two (to (4 '-amyl group cyclohexyl) phenyl) anthracene;
Fig. 2 is the electric current-brightness-voltage curve of embodiment 3 electroluminescent devices;
Fig. 3 is the current efficiency-current density curve of embodiment 3 electroluminescent devices;
Fig. 4 is the luminescent spectrum figure of embodiment 3 electroluminescent devices;
Fig. 5 is 9, the texture pattern of 10-two (to (4 '-amyl group cyclohexyl) phenyl) anthracene.
Embodiment
Embodiment 1,9, the preparation of 10-two (to (4 '-amyl group cyclohexyl) phenyl) anthracene
In the 500mL there-necked flask, add 1.1g Mg bits, 12.4g to amyl group cyclohexyl bromobenzene, is dissolved in 40mLTHF, be added dropwise on a small quantity, add a small amount of iodine again, add thermal initiation with blower, splash into slowly again that remaining temperature is controlled at 40 ℃ to amyl group cyclohexyl bromobenzene, drip off under the room temperature of back and stir 30min.Reaction system is cooled to-70 ℃ with acetone-liquid nitrogen, drips B (OCH
3)
3Solution (2.28g B (OCH
3)
3Be dissolved in 20mLTHF), after dripping off, stir nature and rise to room temperature.Stirring reaction 12 hours adds 10%HCl solution 30mL, splashes into fast and stirs, reflux hydrolysis, 30min postcooling.Use petroleum ether extraction, use anhydrous Na after the saturated common salt washing
2SO
4Drying is revolved steaming, obtains amyl group phenylcyclohexane boric acid crude product 8g.
With 5g 9, the 10-dibromoanthracene is dissolved in the 50mLTHF+50mLN-methyl-2-pyrrolidone, 6g Na
2CO
3Be dissolved in the 45ml water, 5.6g is dissolved in the 40mL ethanolic soln amyl group phenylcyclohexane boric acid, places in the 500mL there-necked flask N together
2Protection adds 0.7g catalyzer (Ph down
3P)
4Pd, reflux is after 3 days, and with benzene dilution, layering, the water dichloromethane extraction merges organic phase, saturated common salt washing, anhydrous Na
2SO
4Drying, revolve steam crude product 5.9g, column chromatography is separated, and obtains 2.7g product 9,10-two (to (4 '-amyl group cyclohexyl) phenyl) anthracene, productive rate 29%.
This compound 9, the fusing point of 10-two (to (4 '-amyl group cyclohexyl) phenyl) anthracene is 276.4 ℃, and clearing point is more than 350 ℃, and solvability is good, is a kind of liquid crystal display material of excellent property.Its nuclear magnetic resonance spectrum as shown in Figure 1; Fig. 5 is the texture pattern of this material under 275 ℃, shows that it has the characteristics of mesomorphic phase.
Embodiment 2,9, and 10-two (to (4 '-amyl group cyclohexyl) phenyl) anthracene prepares electroluminescent device
On a glass substrate that covers by Indium sesquioxide-stannic oxide (ITO) that cleaned, the hole mobile material N for preparing one deck 80 nanometer thickness by the method for vacuum-evaporation, N '-phenylbenzene-N, N '-two (1-naphthyl)-1,1 '-biphenyl-4,4 '-diamines (NPB), on this hole transmission layer, continue then by vacuum evaporation last layer 20 nanometer thickness LCD material 9 of the present invention, 10-two (to (4 '-amyl group cyclohexyl) phenyl) anthracene, on this luminescent layer, continue electron transport material 4 again by vacuum evaporation last layer 30 nanometer thickness, 7-phenylbenzene-1, the adjacent phenanthroline (Bphen) of 10-is at last at the alloy of the vacuum evaporation last layer Mg:Ag negative electrode as device, about 100 nanometers, the back is plated the Ag of 100 nanometers again, promptly obtains electroluminescent device, and this electroluminescent device is as follows:
ITO/NPB (80nm)/LCD material of the present invention (20nm)/Bphen (30nm)/Mg:Ag/Ag
Galvanic positive pole is added on the ITO layer of electroluminescent device, negative pole is added on the Mg:Ag alloy layer, measure the performance of device.Electric current-the brightness of this device-voltage curve such as Fig. 2, current efficiency-current density curve such as Fig. 3, device luminescent spectrum figure such as Fig. 4 from 5V to 13V.
The result shows, can launch bright uniform blue light from the ITO layer of device, and CIE coordinate (0.1544,0.0740) plays bright voltage position 3.5V, and during the 20V of voltage position, high-high brightness is at 1400cd/m
2About, radiative main peak is about 440nm.Device from 5V to the 13V interval in radiative wavelength almost do not change.
Claims (6)
1, structure is suc as formula the organic electroluminescence liquid crystal compound of I,
Wherein, R is that carbonatoms is the alkyl of 1-15.
2, organic electroluminescence liquid crystal compound according to claim 1 is characterized in that: R is an amyl group.
3, the preparation method of the described organic electroluminescence liquid crystal compound of claim 1 comprises the steps:
1) earlier with formula II structure the alkyl-cyclohexyl bromobenzene is prepared as Grignard reagent, again with trimethyl borate B (OCH
3)
3Reaction, generating structure such as formula III to the alkyl-cyclohexyl phenylo boric acid after the hydrolysis;
Wherein, R is that carbonatoms is the alkyl of 1-15;
2) will be to 9 of alkyl-cyclohexyl phenylo boric acid and formula IV structure, the 10-dibromoanthracene is at (Ph
3P)
4Pd catalysis is reaction down, obtains described organic electroluminescence liquid crystal compound;
4, preparation method according to claim 3 is characterized in that: step 2) temperature of described reaction is 100-200 ℃, reaction solvent is THF or N-Methyl pyrrolidone.
5, the application of the described organic electroluminescence liquid crystal compound of claim 1 in the preparation electroluminescent device.
6, the application of the described organic electroluminescence liquid crystal compound of claim 1 in the preparation liquid crystal display material.
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| CNB2005101277972A CN100335591C (en) | 2005-12-07 | 2005-12-07 | Organic electroluminescence liquid crystal compound, and its preparing method and use |
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| CNB2005101277972A CN100335591C (en) | 2005-12-07 | 2005-12-07 | Organic electroluminescence liquid crystal compound, and its preparing method and use |
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|---|---|
| CN1775899A CN1775899A (en) | 2006-05-24 |
| CN100335591C true CN100335591C (en) | 2007-09-05 |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5049455A (en) * | 1984-09-03 | 1991-09-17 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Amphiphilic anthracene derivative |
| JPH09268283A (en) * | 1996-01-29 | 1997-10-14 | Toyo Ink Mfg Co Ltd | Luminescent material for organic electroluminescence element and organic electroluminescent element using the same |
| CN1362464A (en) * | 2002-01-15 | 2002-08-07 | 清华大学 | Organic electroluminescent material |
| JP2002284755A (en) * | 2001-03-26 | 2002-10-03 | Kanto Denka Kogyo Co Ltd | New fluorine-containing anthracene compound and method for manufacturing the same |
-
2005
- 2005-12-07 CN CNB2005101277972A patent/CN100335591C/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5049455A (en) * | 1984-09-03 | 1991-09-17 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Amphiphilic anthracene derivative |
| JPH09268283A (en) * | 1996-01-29 | 1997-10-14 | Toyo Ink Mfg Co Ltd | Luminescent material for organic electroluminescence element and organic electroluminescent element using the same |
| JP2002284755A (en) * | 2001-03-26 | 2002-10-03 | Kanto Denka Kogyo Co Ltd | New fluorine-containing anthracene compound and method for manufacturing the same |
| CN1362464A (en) * | 2002-01-15 | 2002-08-07 | 清华大学 | Organic electroluminescent material |
Non-Patent Citations (1)
| Title |
|---|
| 胺蒽类有机电致发光材料的合成和发光性能的研究 余新明 等，有机化学，第25卷第2期 2005 * |
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