CN100340582C - Fluorophenyl-containing PPV and its uses - Google Patents
Fluorophenyl-containing PPV and its uses Download PDFInfo
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- CN100340582C CN100340582C CNB2005100287197A CN200510028719A CN100340582C CN 100340582 C CN100340582 C CN 100340582C CN B2005100287197 A CNB2005100287197 A CN B2005100287197A CN 200510028719 A CN200510028719 A CN 200510028719A CN 100340582 C CN100340582 C CN 100340582C
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- phenyl
- polystyrene support
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Abstract
The present invention relates to a polystyrene support (FPPV) having electron injection / hole transport capacity and containing a side chain of fluorophenyl and application thereof as electroluminescent materials to an organic flat plate display, which belongs to the technical field of electroluminescent materials. The general formula of the polystyrene support is disclosed at the right, Mn: 36200 to 100000, wherein X 1, X2, X3, X4 and X5 are H or F. At least one of the X1 and the X5 is a hydrogen atom. R is alkyl whose carbon atom number is from 6 to 18. The polymer has favorable solubility, thermal stability and electronic transmission performance, is used as green and blue electroluminescent materials, and is applied to flat plate display devices.
Description
Technical field
The invention belongs to the electroluminescent material technical field, be specifically related to a class and have the outstanding electronics injection and the polystyrene support (FPPV) that contains the fluoro phenyl and the application thereof of cavity transmission ability, relate in particular to a class 2-(2,4 difluorobenzene the base)-support of 5-(4-alkoxyl phenyl) polystyrene (DFPPV) and the application of green electroluminescent material in organic flat-panel monitor thereof.
Background technology
Nineteen ninety is permitted the polymer materials that laboratory [1] finds can be used for polymer LED (PLED) first by Britain's Kevin's enlightening in polystyrene support (PPV), has started the beginning of polymer LED (PLEDs) research.It has characteristics such as long device lifetime, higher internal quantum efficiency, fast-response speed, wide visual angle, low driving voltage; And can control glow color by changing main chain, side-chain structure and composition, realize colored the demonstration; Light-emitting area be can regulate and molecular device, wall-hanging or super slight type color display screen made; Have flexibility and workability simultaneously.Therefore have very wide application prospect, attracted the scientist of increasing country variant and the very big concern and the input of research and commercial undertaking.
According to the relation of luminescence mechanism and structure and performance, scientist and industrial community just actively attempt to develop new and effective stable electroluminescent material at present, to satisfy the colored needs that show of RGB three primary colours; Wait to improve yet the performance of blue light and red light material is anxious.At present the research of relevant PPV derivative mainly concentrates on and improves quantum yield, luminosity, work-ing life and satisfy on the application indexes such as full color demonstration in the world, carries out the preparation of necessity for industrialization.Influencing all multifactor middle electronics of quantum yield and the balance injection in hole is its key factor.PPV itself has good hole transmission performance, and electron-withdrawing group such as F ,-CN or contain N heterocycle azoles etc. and be incorporated into the transmission that helps electronics on PPV main chain/side chain, can improve its quantum yield [2] greatly.Electron-withdrawing substituent (as F ,-CN) the LUMO orbital energy level is reduced, increased electron affinity, and it is little to the influence of HOMO track, give electron substituent group (as-OR) the HOMO orbital energy level is raise, reduced ionizing potential, and little to LUMO orbital energy level influence, and efficient all can be improved under two kinds of factors; The introducing of alkoxyl group simultaneously can also increase the solvability [3] of polymkeric substance.When molecular designing, suitably introduce large volume unit or rigidity liquid crystal cells, reduce the interaction of chain and chain, prevent the fluorescent quenching that electronics causes in the interchain transmission, to improve luminous efficiency; Can improve simultaneously the thermal transition temperature and the stability [4] of polymkeric substance.
Reference
1、Burroughes，J.H.，Jones?C.A.，Friend?R.H.Light?emitting?diodes?basedon?conjugated?polymers.Nature，1990，347：539-541
2a.Wang-Lin?Yu，Hong?Meng，Jian?Pei，and?Wei?Huang?Tuning?Redox?Behaviorand?Emissive?Wavelength?of?Conjugated?Polymers?by?p-n?Diblock?Structures?J.Am.Chem.Soc.，1998，120：11808-11809
2b.Song，S.-Y.；Jang，M.S.；Shim，H.-K.；Song，I.-S.；Kim，W.-H.New?SolubleLight-Emitting?Diode?Polymer?Containing?Oxadiazole?Unit?Synth.Met.，1999，102：1116.
2c.Ronald?M.Gurge，Ananda?M.Sarker，Paul?M.Lahti，Bin?Hu，and?Frank?E.Karasz?Light?Emitting?Properties?of?Fluorine-Substituted?Poly(1，4-phenylenevinylenes)Macromolecule，1997，30(26)：8286-8292
2d.Iris?Benjamin，Erez?Z.Faraggi，Yair?Avny，Dan?Davidov，and?Ronny?NeumannFluorinated?Poly(p-phenylenevinylene)Copolymers：Preparation?and?Use?inLight-Emitting?Diodes?Chem.Master.，1996，8(2)：352-355
2e.Huang?ZH，Duan?XM，Kan?YH，et?al.Influence?of?donor/acceptor?substitutionson?the?properties?of?photo-electricity?in?PPV-Iike?electroluminescent?polymers.Chem.J.Chinese?U.，2002，23(12)：2340-2343
2f.Benjamin?E.，Z.Faraggi，Y.Avny，D.Davidov，R.y?Neumann?FluorinatedPoly(p-phenylenevinlyylene)Copomers：Preparation?and?Use?in?Light-EmittingDiodes.Chem.Materials，1996，8：352-355.
2g.R.M.Gurge，A.M.Sarker，P.M.L?ahti?Karasz?Lig，B.Hu?EmittingProperties?of?Fluorine-Substituted?Poly(1，4-phenylene?vinylenes).Mcromoleacule，1997，30：8286-8292.
2h.R.Riehn，J.Morgado，R.Iqbal，S.C.Moratti，A.B.Holmes，S.Volta，F.Cacialli?Electrochemictroluminesal?and?Eleccent?Properties?of?RandomCopolymers?of?Fluorine?and?Alkoxy?Substituted?Poly(p-phenylene?vinylene)s.Macromolecules，2000，33：3337-3341
3a.Anderson?M.R.，Yu?G，Heeger?A.J.Photoluminescence?and?electroluminescenceof?films?from?soluble?PPV-polymers?Synth.Met.，1997，85(1-3)：1275-6
3b.Pei?Q，Yang?Y.Bright?blue?electroluminescence?from?anoxadiazole-containing?copolymer.Adv?Mater.，1995，7(6)：559-61.
3.c.A.Kraft，A.C.Grimsdale，A.B.Holmes?Electroluminescent?ConjugatedPolymers--Seeing?Polymers?in?a?New?Light.Angew.Chem.Int.Ed.，1998，37：402-428.
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Summary of the invention
The objective of the invention is to propose polystyrene support (FPPV) material that contains fluorophenyl that a class has outstanding electronics injection/cavity transmission ability, and synthetic method, and as the application of blueness-green electroluminescent material in organic flat-panel monitor.
By the methodology of organic synthesis of classics, synthetic a series of polymerisable 1 of fluorophenyl and alkoxyl phenyls that contain, 4-two (brooethyl) benzene derivative, utilize the Gilch reaction to obtain subject polymer easily---polystyrene support (FPPV).Introducing F atom purpose on molecular structure is to introduce electron-withdrawing group, improves its electron transport ability, and quantum yield is improved; (0R) purpose is in order to increase its solvability to introduce alkoxyl group.Simultaneously-0R is for raising the HOMO orbital energy level to electron substituent group, reduce ionizing potential, the F atom is that electron-withdrawing substituent reduces the LUMO orbital energy level, increased electron affinity, give/electron-withdrawing substituent all makes the polymkeric substance energy gap reduce, red shift, the corresponding reduction of trigger voltage take place in ultraviolet-visible maximum absorption and PL spectrum.Introducing the terphenyl purpose on the skeleton is the warping property that increases planes of molecules, reduces the formation of excimer, to improve quantum yield.Utilizing the technology of the present invention route synthetic polymkeric substance is the outstanding electroluminescent material as blueness-green of a class, can be applicable in organic flat-panel monitor.
The polystyrene support (FPPV) that contains fluorophenyl that the present invention proposes has the balanced capacity of outstanding electronics injection/hole transport, high quantum yield, and Heat stability is good, solvability is good, and trigger voltage is low; Structure has following general formula:
Wherein, X
1, X
2, X
3, X
4, X
5=H or F, and X
1-X
4In have one at least for fluorine atom, X
1And X
5Have at least one to be hydrogen atom, R is that carbonatoms is the alkyl of 6-18, and molecular weight is 36200-100000.
Below some polymkeric substance be more typical material, in above-mentioned structure:
(1) X
1,=X
2,=F; X
3=X
4=X
5=H, R are that carbonatoms is the alkyl of 6-18;
(2) X
1,=X
2,=F; X
3=X
4=X
5=H, R are 2-ethylhexyl, n-octyl, positive certain herbaceous plants with big flowers base or positive 12 carbon alkyl;
(3) X
1,=X
3=F, X
2=X
4=X
5=H, R are that carbonatoms is the alkyl of 6-18;
(4) X
1=X
3=F, X
2=X
4=X
5=H, R are 2-ethylhexyl, n-octyl, positive certain herbaceous plants with big flowers base or positive 12 carbon alkyl;
(5) X
1,=X
4=F, X
2=X
3=X
5=H, R are that carbonatoms is the alkyl of 6-18;
(6) X
1,=X
4=F, X
2=X
3=X
5=H, R are the 2-ethylhexyl, n-octyl, positive certain herbaceous plants with big flowers base or positive 12 carbon alkyl.
The synthetic method of the polyphenylacetylene support that the present invention proposes is as follows:
With 2,5-dibromo p-Xylol is a starting raw material, close Suzuki reaction under palladium (O) catalysis by twice at four (triphenyl phosphorus), successively with 4-alkoxy benzene ylboronic acid and the reaction of fluorine-containing phenyl-boron dihydroxide, generation has 2-fluorophenyl-5-(4-alkoxyl phenyl) p-Xylol of terphenyl structure, in tetracol phenixin, cause again with azo isobutyl fine (AIBN), generate a series of polymerisable l that contain fluorophenyl and alkoxyl phenyl with the NBS reaction, 4-two (brooethyl) benzene derivative, utilize the Gilch reaction at room temperature to make solvent, can obtain subject polymer (FPPV) easily under the t-BuOK catalysis with THF.
Concrete synthetic route is as follows:
All polymkeric substance all have good solvability in chloroform, tetrahydrofuran (THF) equal solvent, initial decomposition temperature is above 350 ℃.
Description of drawings
The UV-vis of Fig. 1 polymkeric substance 2 and PL spectrogram.
Embodiment
In order to understand content of the present invention better, further specify technical scheme of the present invention below by specific embodiment.
Poly-2-(2,4 difluorobenzene base)-5-(4-(2-ethyl hexyl oxy) phenyl)-1,4-phenylene ethylene (DFEHPPV), (being called for short polymkeric substance 2) synthetic, concrete steps are as follows:
1,4-2-ethyl hexyl oxy bromobenzene is synthetic: at lucifuge and N
2Under the condition, inject 200 milliliters of exsiccant DMF in the interior airtight flask that right-bromophenol 17.30 grams (0.10 mole) and salt of wormwood 39.2 mixtures are housed, be added dropwise to 2-ethylhexyl bromine 19.2 grams (18.0 milliliters, 0.10 mole) again, stir and slowly heat liter down, and be incubated 18 hours surely to 60 ℃.Filter, with 1M hydrochloric acid, Skellysolve A cancellation, water extracts with Skellysolve A, organic phase salt acid elution, the organic phase that merges uses 3M aqueous sodium hydroxide solution, water washing to neutral successively, anhydrous magnesium sulfate drying spends the night, and revolves to steam to desolventize, must restrain by slightly yellowy liquid 19.58, crude product carries out silica gel column chromatography with normal hexane as eluent, obtains colourless liquid 18.46 grams, yield 65%.
2,4-(2-ethyl hexyl oxy) phenyl-boron dihydroxide is synthetic: at N
2Under the condition, 4-(2-ethyl hexyl oxy) bromobenzene (18.00 grams inwardly are housed, 65.00 inject 300 milliliters of new THF that steam in flask mmole), dry ice is cooled to-78 ℃, adds the n-Butyl Lithium (hexane solution of 1.6M, 60.00 milliliter, 96.00 mmole), be incubated after 1 hour, inject (20.00 milliliters of trimethyl borate 18.54 grams, 178.00 mmole), spend the night under the room temperature.With the cancellation of 2.0M hydrochloric acid, massive laundering, water extracted with diethyl ether,, spend the night with the organic phase that anhydrous magnesium sulfate drying merges.Revolve steaming and desolventize, crude product carries out silica gel column chromatography with petrol ether/ethyl acetate as eluent, obtains colourless viscous liquid 14.46 grams, yield 89.04%.
3,2-bromo-5-(4-(2-ethyl hexyl oxy) phenyl) p-Xylol is synthetic: lucifuge is led to N
2Under the condition, add 5 milliliters of 4-(2-ethyl hexyl oxy) phenyl-boron dihydroxide 12.60 grams (50.40 mmole), 200 milliliters of toluene, 1M aqueous sodium carbonate, 2,4-dibromo p-Xylol 10.52 grams (40.00 mmole) and palladium catalyst 1.384 grams (1.2 mmole) are to airtight three-necked bottle, 80 ℃ of insulations 72 hours; Add methylene dichloride and tell organic phase immediately, the saturated common salt water washing, anhydrous magnesium sulfate drying spends the night.Obtain crude product after revolving steaming, do eluent with sherwood oil and carry out silica gel column chromatography, obtain colourless liquid 8.84 grams, yield 56.96%.
4,2-(2,4 difluorobenzene base)-5-(4-(2-ethyl hexyl oxy) phenyl) p-Xylol is synthetic: lucifuge is led to N
2Under the condition, add 2,4-difluorophenyl boric acid 2.052 grams (13.00 mmole), 200 milliliters of toluene, 3 milliliters of 1M aqueous sodium carbonates, 2-bromo-5-(4-(2-ethyl hexyl oxy) phenyl) p-Xylol 3.88 grams (10.00 mmole) and palladium catalyst 0.462 grams (0.40 mmole) are to airtight three-necked bottle, 80 ℃ of insulations 72 hours; Add methylene dichloride and tell organic phase immediately, the saturated common salt water washing, anhydrous magnesium sulfate drying spends the night.Revolve and steam the back, do eluent with sherwood oil and carry out silica gel column chromatography, obtain colourless viscous liquid 2.53 grams, yield 60.00% to crude product.
5,2-(2,4 difluorobenzene base)-5-(4-(2-ethyl hexyl oxy) phenyl) synthesizing dibromomethylbenzene: lucifuge is led to N
2Under the condition, add 2-(2, the 4-difluorophenyl)-5-(4-(2-ethyl hexyl oxy) phenyl) p-Xylol 0.844 gram (2.00 mmole), 120 milliliters of tetracol phenixin, NBS1.068 gram (3.00 mmole) and azo isobutyl cyanogen (AIBN) extremely in the airtight three-necked bottle, refluxed 4 hours; Cooling is filtered, and filtrate concentrates, and the normal hexane washing is done eluent with sherwood oil/methylene dichloride again and carried out silica gel column chromatography, obtains slightly yellow look white solid 0.5048 gram, yield 43.00%.
6, poly-2-(2,4 difluorobenzene base)-5-(4-(2-ethyl hexyl oxy) phenyl) phenylene ethylene (DFEHPPV) is synthetic: at frozen water cooling N
2Inject under the condition with 5.0 milliliters of new poly-2-(2 of THF dissolving that steam, the 4-difluorophenyl)-5-(4-(2-ethyl hexyl oxy) phenyl) phenylene ethylene (DFEHPPV) 0.294 gram (0.5 mmole), drip with 30 milliliters of new THF dissolving t-BuOK 0.257 gram (2.30 mmole) solution that steam, stirring reaction is 24 hours under the room temperature; Said mixture to going into precipitating in the methyl alcohol, is filtered, and precipitation is poured precipitating in the methyl alcohol into, repeatedly several times again with the chloroform dissolving.Obtain green powder solid 0.093 gram, yield 44.50%.
7, luminosity: Fig. 1 has provided UV-vis and the PL spectrogram of polymkeric substance 2 in the 1ppm chloroformic solution, and ultraviolet maximum absorption wavelength is 382nm, and the PL maximum emission wavelength is 499nm, and the half-breadth peak is 80nm, is a kind of ideal green electroluminescent material.Can be used in organic flat-panel display device.
Use the reaction of different bromoalkanes and p bromophenol, can generate different 4-alkoxyl group bromobenzenes, further obtain 4-alkoxy benzene ylboronic acid.This thing and different fluorine-containing phenyl-boron dihydroxide are successively with 2, and the reaction of 5-two bromo-p-Xylol can further generate different 2-fluoro phenyl-5 (4-alkoxyl phenyl)-p-Xylol.By the MBS bromination, can obtain other polymerisable monomers.By identical polyreaction, can obtain corresponding polymer.These polymkeric substance have and embodiment polymer phase similar performance, can be used for organic flat-panel display device.
Claims (6)
1, a kind of polystyrene support that contains the fluoro phenyl is characterized in that general structure is as follows:
Wherein, X
1, X
2, X
3, X
4, X
5Be H or F, and X
1, X
2, X
3And X
4In have one at least for fluorine atom, X
1And X
5Have at least one to be hydrogen atom; R is that carbonatoms is the alkyl of 6-18, and molecular weight is 36200-100000.
2,, it is characterized in that a kind of for following material as the said polystyrene support that contains the fluoro phenyl of claim 1:
(1)X
1，＝X
2，＝F；X
3＝X
4＝X
5＝H；
(2)X
1，＝X
3＝F，X
2＝X
4＝X
5＝H；
(3)X
1，＝X
4＝F，X
2＝X
3＝X
5＝H。
3, the polystyrene support that contains the fluoro phenyl according to claim 2 is characterized in that R is the 2-ethylhexyl, n-octyl, positive certain herbaceous plants with big flowers base or positive 12 carbon alkyl.
4, the synthetic method of polymkeric substance as claimed in claim 1 or 2, it is characterized in that with 2,5-dibromo p-Xylol is a starting raw material, close Suzuki reaction under palladium (0) catalysis by twice at four (triphenyl phosphorus), successively with 4-alkoxy benzene ylboronic acid and the reaction of fluorine-containing phenyl-boron dihydroxide, generation has 2-fluorophenyl-5-(4-alkoxyl phenyl) p-Xylol of terphenyl structure, in tetracol phenixin, use the fine initiation of azo isobutyl again, generate a series of polymerisable 1 of fluorophenyl and alkoxyl phenyls that contain with the NBS reaction, 4-two (brooethyl) benzene derivative, utilize the Gilch reaction at room temperature to make solvent, can obtain subject polymer easily under the t-BuOK catalysis with THF.
5, as the said application that contains the polystyrene support of fluoro phenyl as blueness-green electroluminescent material of claim 1.
6, contain the polystyrene support of fluoro phenyl as the application of green electroluminescent material in organic flat-panel monitor as claim 1 is said.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100410292C (en) * | 2006-04-27 | 2008-08-13 | 复旦大学 | Polyphenylene ethylene and its derivant, preparation process and application |
| CN101307005B (en) * | 2008-07-01 | 2012-05-09 | 华南理工大学 | Ionic cathode cushioning layer material, method for preparing same and applications |
| CN112778679B (en) * | 2020-12-31 | 2023-09-29 | 苏州市新广益电子股份有限公司 | High-strength and high-thermal-stability poly-4-methyl-1-pentene microporous membrane and preparation method thereof |
Citations (4)
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|---|---|---|---|---|
| US6403238B1 (en) * | 1998-07-10 | 2002-06-11 | Hoerhold Hans-Heinrich | Organic light-emitting diodes (OLED) including poly[2-methoxy-5-(2′-ethyl-hexyloxy)-1,4-phenylene-1,2-ethenylene-2,5-dimethoxy-1,4-phenylene-1,2-ethenylene] as electroluminescent material |
| CN1454961A (en) * | 2003-05-15 | 2003-11-12 | 中国科学院长春应用化学研究所 | Transmission type polymer electroluminescent material and preparing method thereof |
| CN1587300A (en) * | 2004-07-15 | 2005-03-02 | 复旦大学 | Modified soft and hard multiple block conjugate polymer and its preparing method |
| CN1600759A (en) * | 2003-09-22 | 2005-03-30 | 吉林大学 | Luminescence oligomer in PPV category of containing biphenyl center |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6403238B1 (en) * | 1998-07-10 | 2002-06-11 | Hoerhold Hans-Heinrich | Organic light-emitting diodes (OLED) including poly[2-methoxy-5-(2′-ethyl-hexyloxy)-1,4-phenylene-1,2-ethenylene-2,5-dimethoxy-1,4-phenylene-1,2-ethenylene] as electroluminescent material |
| CN1454961A (en) * | 2003-05-15 | 2003-11-12 | 中国科学院长春应用化学研究所 | Transmission type polymer electroluminescent material and preparing method thereof |
| CN1600759A (en) * | 2003-09-22 | 2005-03-30 | 吉林大学 | Luminescence oligomer in PPV category of containing biphenyl center |
| CN1587300A (en) * | 2004-07-15 | 2005-03-02 | 复旦大学 | Modified soft and hard multiple block conjugate polymer and its preparing method |
Non-Patent Citations (2)
| Title |
|---|
| PPV衍生物的研究进展及应用前景 余淑娴，杨廷达，江西科学，第22卷第1期 2004 * |
| 含PPV结构的电致发光材料 李会学，萧泰，西北师范大学学报(自然科学版)，第39卷第03期 2003 * |
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