CN1803865A - P-phenylene vinylene(PPV) containing fluoryl and difluoro substituted phenyl side chain, its preparation method and application - Google Patents
P-phenylene vinylene(PPV) containing fluoryl and difluoro substituted phenyl side chain, its preparation method and application Download PDFInfo
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- CN1803865A CN1803865A CN 200510111060 CN200510111060A CN1803865A CN 1803865 A CN1803865 A CN 1803865A CN 200510111060 CN200510111060 CN 200510111060 CN 200510111060 A CN200510111060 A CN 200510111060A CN 1803865 A CN1803865 A CN 1803865A
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Abstract
The invention relates to the field of electroluminescent material, and discloses a category of p-phenylene vinylene containing fluorenyl and difluorobenzene side chains (FDFPPV) having electron injection / cavity transmitting capacity, their copolymers and method for synthesizing. These polymeric compounds have good dissolubility, thermal stability and electronic conveyance, thus can be used as green-red electroluminescent material for panel displays.
Description
Technical field
The invention belongs to the electroluminescent material technical field, be specifically related to a class side chain and contain polystyrene support (FDFPPV) and the multipolymer thereof of fluorenyl and phenyl-difluoride base, with and preparation method thereof and application in electroluminescent, relate in particular to class 2-(2 ', 4 '-difluorophenyl)-5-(9 ' 9 '-dialkyl group fluorenyl-2 ')-polystyrene support (FDFPPV) and multipolymer thereof and as the application of green-red electroluminescent materials in organic flat-panel monitor.
Background technology
Nineteen ninety is permitted the polymer materials that the laboratory 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 research.
[1]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.
[14]
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, and particularly green glow and red light material are carried 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 transport performance, and electron-withdrawing group such as F, and-CN or contain N heterocycle etc. and be incorporated into the transmission that helps electronics on PPV main chain/side chain can improve its quantum yield greatly.
[2-13]Fluorine atom, cyano group reduce the LUMO orbital energy level as electron-withdrawing substituent, increased electron affinity, improved the mobility of electronics, fluorenyl is incorporated in the biphenyl structural, can reduce the coplanarity of modular construction, reduce the interaction of chain and chain, prevent the fluorescent quenching that electronics causes in the interchain transmission, the both can improve luminous efficiency; Can improve simultaneously the thermal transition temperature and the stability of polymkeric substance.
[10-13]Can regulate its emission wavelength by copolymerization, improve quantum yield.
Reference
1、Burroughes，J.H.，Jones?C.A.，Friend?R.H.Light?emitting?diodes?based?onconjugated?polymers.Nature，1990，347：539-541
2、Yu?W.H.，Meng?H.，Pei?J.，and?Huang?W.Tuning?Redox?Behavior?and?EmissiveWavelength?of?Conjugated?Polymers?by?p-n?Diblock?Structures?J.Am.Chem.Soc.，1998，120：11808-11809；
3、Xiao?Y.，Yu?W.L.，Chua?S.J.，and?Huang?W.A?novel?series?of?copolymerscontaining?2，5-dicyano-1，4-phenylenevinylene-Synthetic?tuning?of?the?HOMO?andLUMO?energy?levels?of?conjugated?polymers.Chem.Eur.J，2000，6(8)，1318
4、Chung?S.J.，Kwon?K.Y，Lee?S.W.，Jin?J.I.，Lee?C.H.，Lee?C.E.，Park?Y.Highlyefficient?light-emitting?diodes?based?on?an?organic-soluble?poly(p-phenylenevinylene)derivative?carrying?the?electron-transporting?PLED?moiety，Advanced?Materials，1998，10(14)：1112
5、Gurge?R.M.，Sarker?A.M.，Lahti?P.M.，Hu?B.，and?Karasz?F.E.，Light?EmittingProperties?of?Fluorine-Substituted?Poly(1，4-phenylene?vinylenes)Macromolecule，1997，30(26)：8286
6、Benjamin?I.，Faraggi?E.Z.，Avny?Y.，Davidov?D.，and?Neumann?R.，Fluorinated?Poly(p-phenylenevinylene)Copolymers：Preparation?and?Use?in?Light-Emitting?DiodesChem.Mater.，1996，8(2)：352
7、Huang?Z.H.，Duan?X.M.，Kan?Y.H.，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
8、Gurge?R.M.，Sarker?A.M.，L?ahti?P.M.，et?al.Emitting?Properties?ofFluorine-Substituted?Poly(1，4-phenylene?vinylenes).Mcromoleacule，1997，30：8286
9、Yu?L.S.and?Chen?S.A.，Full-Range?Tunability?of?Electron?and?Hole?CarrierMobilities?and?Density?Ratios?via?Iicorporation?of?Highly?Electron-Deficient?Moietiesin?Poly(phenylene?vinylene)Side?Chains?Advanced?Materials，2004，16(8)：744
10、Egbe?D.A.M.，Kietzke.T，Carbonnier?B.，Muhlbacher?D.，Horhold?H.H.，Neher?D.，Pakula?T.，Synthesis，characterization，and?photophysical，electrochemical，electroluminescent，and?photovoltaic?properties?of?yne-containing?CN-PPVs，Macromoleculers，2004，37(24)：8863
11、Jin?Y.，Kim?J.，Lee?S.，Kim?J.Y.，Park?S.H.，Lee?K.，Suh?H.，Novel?electroluminescentpolymers?with?fluoro?groups?in?vinylene?units，Macromoleculers，2004，37(18)：6711
12、Wang?H.M.，Tductingao?X.M.，Newton?E.，Thermal?degradation?kinetics?andlifetime?prediction?of?a?luminescent?co-polymer，Polymer?Int.，2004，53(1)：20
13、Su?H.J.，Wu?F.I.，Shu?C.F.，Tuning?wavelength：Synthesis?and?characterization?ofspiro-DPVF-containing?polyfluorenes?and?applications?in?organic?Iight-emittingdiodes?Macromoleculers，2004，37(19)：7197
14、Akcelrud?L.?Electroluminescent?polymers?Progress?in?Polymer?Science，2003，28，875
15、Neef，C.J.；Ferraris，J.P.MEH-PPV：Improved?Synthetic?Procedure?and?MolecularWeight?Control?Macromolecules?2000，33，2311
Summary of the invention
The polystyrene support (FDFPPV) and the copolymer material thereof that contain fluorenyl and phenyl-difluoride base side chain that a class has electronics injection/cavity transmission ability have been the objective of the invention is to propose, and synthetic method, and as the application of electroluminescent material in organic flat-panel monitor.
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 2,4-difluorophenyl boric acid and 9, the reaction of 9-dialkyl group fluorenes boric acid-2 generates a series of 2-(2 ', 4 '-difluorophenyl)-5-(9 ', 9 '-dialkyl group fluorenyl-2 ')-1, the 4-p-Xylol causes with azo isobutyl fine (AIBN) in tetracol phenixin again, with the synthetic a series of polymerisable 2-(2 ' of NBS reaction, 4 '-difluorophenyl)-5-(9 ', 9 '-dialkyl group fluorenyl-2 ')-1,4-two (brooethyl) benzene (compound 7) utilizes the Gilch reaction to obtain polymkeric substance (FDFPPV) easily.Simultaneously according to document
[3,9,15]Method is synthesized comonomer 2,5-dicyano-1,4-two (brooethyl) benzene (compound 8) and 2,5-dialkoxy-1,4-two (brooethyl) benzene (compound 9) is by different ratios and 2-(2 ', 4 '-difluorophenyl)-5-(9 ', 9 '-dialkyl group fluorenyl-2 ')-1,4-two (brooethyl) benzene (compound 7) copolymerization under t-BuOK catalysis can obtain their multipolymer easily.Introducing F atom purpose on molecular structure is to introduce electron-withdrawing group, improves its electron transport ability, and quantum yield is improved; Introduce the fluorenyl purpose and be in order to increase nonplanarity, to reduce the interchain cancellation, improve quantum yield, it is stability and solvability in order to improve polymkeric substance that 9 of fluorenyls are introduced alkyl; Can regulate glow color by changing comonomer ratio, raise the efficiency.Utilizing the technology of the present invention route synthetic polymkeric substance is the outstanding green-red electroluminescent materials of a class, can be applicable in organic dull and stereotyped electroluminescent display.
The polystyrene that contains fluorenyl and phenyl-difluoride base side chain that the present invention proposes supports (FDFPPV) and multipolymer quantum yield height thereof, Heat stability is good, solvability is fabulous in usual vehicle, has outstanding electronics injection/cavity transmission ability.Its general formula is as follows:
Below some polymkeric substance be more typical material, in above-mentioned structure:
(1) 0＜x≤1, x+y=1; R
1=R
2=CN; R
3=R
4=carbonatoms is the alkyl of 4-12.
(2) 0＜x≤1, x+y=1; R
1=R
2=CN; R
3=R
4=hexyl, 2-ethylhexyl, n-octyl.
(3) 0＜x≤1, x+y=1; R
1, R
2=carbon atom is the alkoxyl group of 1-8; R
3=R
4=carbonatoms is the alkyl of 4-12.
(4) 0＜x≤1, x+y=1; R
1, R
2=methoxyl group, n-butoxy, hexyloxy, 2-ethyl hexyl oxy and n-octyloxy; R
3=R
4=carbonatoms is the alkyl of 4-12.
(5) 0＜x≤1, x+y=1; R
1, R
2=methoxyl group, n-butoxy, hexyloxy, 2-ethyl hexyl oxy and n-octyloxy; R
3=R
4=hexyl, 2-ethylhexyl and n-octyl.
(6) 0＜x≤1, x+y=1; R
1=methoxyl group, R
2=2-ethyl hexyl oxy; R
3=R
4=hexyl, 2-ethylhexyl and n-octyl.
The synthetic method of the polymkeric substance 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 2,4-difluorophenyl boric acid and 9,9-dialkyl group fluorenes boric acid-2 (compound 4) reaction, generate a series of 2-(2 ', 4 '-difluorophenyl)-5-(9 ', 9 '-dialkyl group fluorenyl-2 ')-1,4-p-Xylol (compound 6) causes with azo isobutyl fine (AIBN) in tetracol phenixin again, with the synthetic a series of polymerisable 2-(2 ' of NBS reaction, 4 '-difluorophenyl)-5-(9 ', 9 '-dialkyl group fluorenyl-2 ')-1,4-two (brooethyl) benzene (compound 7) utilizes Gilch to be reflected in the tetrahydrofuran (THF) with obtaining polymkeric substance (FDFPPV) under the t-BuOK catalysis easily.Wherein 9, through alkylation, bromination and three steps of boration and obtain, buied by Aldrich company by the 2,4 difluorobenzene ylboronic acid by fluorenes for 9-dialkyl group fluorenes boric acid-2 (compound 4).Simultaneously according to document
[3,9,15]Method is with 2,5-two bromo-p-Xylol are the synthetic comonomer 2 of raw material, 5-dicyano-1,4-two (brooethyl) benzene (compound 8) and be the raw material Synthetic 2 with Resorcinol or p methoxy phenol, 5-dialkoxy-1,4-two (brooethyl) benzene (compound 9), in tetrahydrofuran (THF) with under the t-BuOK catalysis in varing proportions with 2-(2 ', 4 '-difluorophenyl)-5-(9 ', 9 '-dialkyl group fluorenyl-2 ')-1,4-two (brooethyl) benzene (compound 7) copolymerization can obtain their multipolymer easily.Synthetic route is as follows:
All polymkeric substance all have good solvability in chloroform, tetrahydrofuran (THF), toluene equal solvent, initial decomposition temperature reaches 400 ℃.
Description of drawings
Fig. 1, Fig. 2 are the UV-vis and the PL spectrogram of polymkeric substance 1 and 2.
Fig. 3 is the thermogravimetric analysis figure of polymkeric substance 1.
The UV-vis of Fig. 4 polymkeric substance 3 and PL spectrogram.
Embodiment
In order to understand the content of patent of the present invention better, further specify technical scheme of the present invention below by specific embodiment.
1.2-bromo-5-(2, the 4-difluorophenyl)-p-Xylol (compound 5) synthetic: under lucifuge and condition of nitrogen gas, inject 150 milliliters of toluene in interior 5.26 gram (20.0 mmoles) 2 that are equipped with, 5-two bromo-p-Xylol, 3.14 gram (20.0 mmoles) 2, in the airtight flask of 4-difluorophenyl boric acid and 692 milligrams of (0.6 mmole) palladiums (0) mixture of catalysts, be added dropwise to the aqueous sodium carbonate of 30 milliliter of 1.0 mol again, stir down slowly heating and rise, and be incubated 72 hours surely to 85 ℃.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 3.88 grams, yield 65.5%.
2.9, synthesizing of 9-dioctyl fluorene (compound 2): 8.3 gram (50.0 mmole) fluorenes are dissolved in 50 milliliters of tetrahydrofuran (THF)s, drip 25 milliliters of (62.5 mmoles down at-78 ℃, 2.5 the n-Butyl Lithium hexane solution of mol), under nitrogen atmosphere, react 1h, drip the mixed solution of 21.2 gram (110 mmole) 1-bromooctanes and 20 milliliters of tetrahydrofuran (THF)s again, at room temperature stir until redness then and disappear. reaction solution is poured into also used extracted with diethyl ether in the distilled water, organic layer is with the saturated common salt water washing and use anhydrous magnesium sulfate drying. and decompression removes down and desolvates, underpressure distillation obtains yellow oily liquid 18.3 grams, yield 93.8% after removing unnecessary 1-bromooctane again.
3.9, synthesizing of 9-dioctyl-2-bromine fluorenes (compound 3): 7.8 gram (20 mmole) compounds 2 are dissolved in 50 milliliters of chloroforms,, add the Fe powder again, in the time of 0 ℃, add bromine water, room temperature reaction 7 hours is poured reaction mixture in the water into and is disappeared the water layer chloroform extraction until redness with the hypo solution washing, mix the organic layer anhydrous magnesium sulfate drying. except that after desolvating, further do the silica gel column chromatography separation of wash-out, obtain colourless liquid 8.05 grams, yield 86% with normal hexane.
4.9,9-dioctyl fluorene-2-boric acid (compound 4) synthetic: at N
2Under the condition, inwardly being equipped with 4.68 digests and injects 60 milliliters of new THF that steam in the flask of compound 2 (10.00 mmole), dry ice is cooled to-78 ℃, add 10.00 milliliters of n-Butyl Lithium (hexane solutions of 1.6M, 16.00 mmole), be incubated after 1 hour, inject (3.20 milliliters of trimethyl borate 3.12 grams, 30.00 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 3.14 grams, yield 72.4%.
5.2-(2,4 difluorobenzene base)-5-(9,9-dioctyl fluorenyl-2)-p-Xylol (compound 6) is synthetic: at lucifuge and logical N
2Under the condition, add 4,50 milliliters of toluene of 2.60 gram (6.0 mmole) compounds, 10 milliliters of aqueous sodium carbonate (1.0 mol, 20 mmoles), 1.48 digest compound 5 (5.0 mmole) and palladium catalyst 138 milligrams (0.12 mmoles) 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 3.69 grams, yield 60.90%.
(6.2-2,4 difluorobenzene base)-5-(9,9-dioctyl fluorenyl-2)-synthesizing: at lucifuge and N to dibromomethylbenzene (compound 7)
2Under the condition, inject 100 milliliters of tetracol phenixin to the airtight three-necked bottle that 3.35 gram (0.5 mmole) compounds, 6,1.78 gram (1.00 mmole) N-bromo-succinimides (NBS) and a little azo isobutyl cyanogen (AIBN) are housed, back flow reaction 2-4 hour; Cooling is filtered, and filtrate concentrates.Do eluent with sherwood oil/methylene dichloride and carry out silica gel column chromatography, obtain light yellow thick liquid 1.55 grams, yield 40.60%.
7. poly-2-(2,4 difluorobenzene base)-5-(9,9-dioctyl fluorenyl-2) phenylene ethylene (DOFDFPPV, P1) synthetic: at frozen water cooling N
2Inject under the condition with 10.0 milliliters of new tetrahydrofuran (THF) (THF), 2.5 milliliters of potassium tert.-butoxide tetrahydrofuran solution (1.0 mol of steaming, 2.0 mmole), stir the mixture that dropwise adds 382 milligrams of (0.5 mmole) compounds 7 and 20 milliliters of tetrahydrofuran (THF)s down, system becomes cyan solution by light yellow transparent solution immediately, and green fluorescence occurs simultaneously.Continued at room temperature stirring reaction 12 hours; Said mixture to going into precipitating in methyl alcohol and the hydrochloric acid, is filtered.The precipitating thing dissolves with tetrahydrofuran (THF), filters, and filtrate is poured precipitating in the methyl alcohol again into, and repeatedly several times, vacuum-drying under 40 ℃ of conditions obtains 154.0 milligrams of green fiber shape materials, yield 51.20%.
Embodiment 2: multipolymer
Reference literature
[3,9,15]Method synthetic compound 8 and compound 9 easily.
Synthesizing of multipolymer (P2): under frozen water cool nitrogen condition, inject with 10.0 milliliters of new tetrahydrofuran (THF), 4.0 milliliters of potassium tert.-butoxide tetrahydrofuran solution (1.0 mol of steaming, 4.0 mmole), stir and dropwise add 7,124.4 milligrams of (0.4 mmoles) 2 of 305.6 milligrams of (0.4 mmole) compounds down, 5-dicyano-1, the mixture of 4-xylylene bromide (compound 8) and 40 milliliters of tetrahydrofuran (THF)s, system becomes cyan solution by light yellow transparent solution immediately, and green fluorescence occurs simultaneously.Continued at room temperature stirring reaction 12 hours; Said mixture to going into precipitating in methyl alcohol and the hydrochloric acid, is filtered.The precipitating thing dissolves with tetrahydrofuran (THF), filters, and filtrate is poured precipitating in the methyl alcohol again into, and repeatedly several times, vacuum-drying under 40 ℃ of conditions obtains 130.1 milligrams of green fiber shape materials, yield 42.8%.
Synthesizing of multipolymer (P3): under frozen water cool nitrogen condition, inject with 10.0 milliliters of new tetrahydrofuran (THF), 5.0 milliliters of potassium tert.-butoxide tetrahydrofuran solution (1.0 mol of steaming, 5.0 mmole), stir and dropwise add 152.8 milligrams of (0.2 mmole) 7,336.0 milligrams of (0.8 mmole) 2-methoxyl groups-5 of compound (2 '-ethyl hexyl oxy)-1 down, the mixture of 4-xylylene bromide (compound 9) and 40 milliliters of tetrahydrofuran (THF)s, system becomes orange-red solution by light yellow transparent solution immediately, and fluorescent red-orange occurs simultaneously.Along with the prolongation in reaction times, color burn, viscosity strengthens.Continued at room temperature stirring reaction 12 hours; Said mixture to going into precipitating in methyl alcohol and the hydrochloric acid, is filtered.The precipitating thing dissolves with tetrahydrofuran (THF), filters, and filtrate is poured precipitating in the methyl alcohol again into, and repeatedly several times, vacuum-drying under 40 ℃ of conditions obtains 168.2 milligrams of red fibrous materials, yield 51.8%.
8. light property: Fig. 1 and Fig. 2 have provided P1 and UV-vis and the PL spectrogram of P2 in 1ppm chloroform and THF solution, ultraviolet maximum absorption wavelength is respectively 402 and 410 nanometers, the PL maximum emission wavelength is respectively 486 and 492 nanometers, about 60 nanometers in half-breadth peak are a kind of ideal green electroluminescent materials.Can be applied in organic flat-panel display device.Fig. 4 has provided P31ppm chloroformic solution and solid-state UV-vis and PL spectrogram, and the solution maximum absorption wavelength is 488 nanometers, and maximum emission wavelength is 560 nanometers in the solution, and solid-state maximum emission wavelength is 604 nanometers, belongs to red light material.
Other intermediates and polymkeric substance are synthetic with reference to above method.Use different bromoalkane synthetic different 9,9-dialkyl group fluorenes boric acid-2 (compound 4), obtain 9 of fluorenes through series reaction, 9 have different alkyl to replace 2-(2 ', 4 '-difluorophenyl)-and 5-(9 ', 9 '-dialkyl group fluorenyl-2 ')-1,4-dibromomethylbenzene (compound 7), same these monomers can autohemagglutination and can with compound 8 or compound 9 copolymerization in varing proportions, can obtain the multipolymer of different emission wavelengths.These polymkeric substance and multipolymer have and performance like the embodiment polymer class, can be used as electroluminescent material and are applied in organic flat-panel display device.
Claims (5)
1, a kind of polystyrene support and multipolymer thereof that contains fluorenyl and phenyl-difluoride base side chain, its structural formula is as follows:
Wherein: R
1, R
2Be CN, or carbon atom is the alkoxyl group of 1-8; R
3, R
4For carbonatoms is the alkyl of 4-12; 0＜x≤1, x+y=1.
2,, it is characterized in that a kind of for following material as said polystyrene support and the multipolymer thereof that contains fluorenyl and phenyl-difluoride base side chain of claim 1:
(1) 0＜x≤1, x+y=1; R
1, R
2Be CN; R
3, R
4For carbonatoms is the alkyl of 4-12;
(2) 0＜x≤1, x+y=1; R
1, R
2Be CN; R
3, R
4Be hexyl, 2-ethylhexyl or n-octyl;
(3) 0＜x≤1, x+y=1; R
1, R
2For carbon atom is the alkoxyl group of 1-8; R
3, R
4For carbonatoms is the alkyl of 4-12;
(4) 0＜x≤1, x+y=1; R
1, R
2Be methoxyl group, n-butoxy, hexyloxy, 2-ethyl hexyl oxy or n-octyloxy; R
3, R
4For carbonatoms is the alkyl of 4-12;
(5) 0＜x≤1, x+y=1; R
1, R
2=methoxyl group, n-butoxy, hexyloxy, 2-ethyl hexyl oxy or n-octyloxy; R
3, R
4Be hexyl, 2-ethylhexyl or n-octyl;
(6) 0＜x≤1, x+y=1; R
1Be methoxyl group, R
2Be the 2-ethyl hexyl oxy; R
3, R
4Be hexyl, 2-ethylhexyl or n-octyl.
3, the synthetic method of a kind of claim 1 or 2 said polymkeric substance, 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 2,4-difluorophenyl boric acid and 9, the reaction of 9-dialkyl group fluorenes boric acid-2, generate a series of 2-(2 ', 4 '-difluorophenyl)-and 5-(9 ', 9 '-dialkyl group fluorenyl-2 ')-1, the 4-p-Xylol, in tetracol phenixin, use the fine initiation of azo isobutyl again, a series ofly polymerisablely contain 9 with N-bromosuccinimide reaction is synthetic, 9-two replaces 1 of fluorenyls and 2,4 difluorobenzene base, 4-two (brooethyl) benzene and derivative thereof utilize the Gilch reaction to obtain polymkeric substance.Simultaneously according to the synthetic comonomer 2 of ordinary method, 5-dicyano-1,4-two (brooethyl) benzene and 2,5-dialkoxy-1,4-two (brooethyl) benzene is by different ratios and 2-(2 ', 4 '-difluorophenyl)-5-(9 ', 9 '-dialkyl group fluorenyl-2 ')-1, the copolymerization under t-BuOK catalysis of 4-two (brooethyl) benzene obtains their multipolymer.
4, as the application of the said polystyrene support that contains fluorenyl and phenyl-difluoride base side chain of claim 1 and multipolymer thereof as green-red electroluminescent materials.
5, as the said polystyrene support that contains fluorenyl and phenyl-difluoride base side chain of claim 1 and multipolymer thereof as the application of green-red electroluminescent materials in organic flat-panel monitor.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102344369A (en) * | 2010-07-30 | 2012-02-08 | 华东师范大学 | High oriented luminescent polyacetylene monomer with side chains containing fluorene group and preparation method thereof |
| CN113583511A (en) * | 2020-04-30 | 2021-11-02 | Tcl科技集团股份有限公司 | Ink, quantum dot film and quantum dot light-emitting diode |
-
2005
- 2005-12-01 CN CN 200510111060 patent/CN1803865A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102344369A (en) * | 2010-07-30 | 2012-02-08 | 华东师范大学 | High oriented luminescent polyacetylene monomer with side chains containing fluorene group and preparation method thereof |
| CN113583511A (en) * | 2020-04-30 | 2021-11-02 | Tcl科技集团股份有限公司 | Ink, quantum dot film and quantum dot light-emitting diode |
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