CN101362820A - Blue hyper-branched polymer electroluminescent materials using pyrazoline unit as nuclear and preparation method thereof - Google Patents
Blue hyper-branched polymer electroluminescent materials using pyrazoline unit as nuclear and preparation method thereof Download PDFInfo
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- CN101362820A CN101362820A CNA2008101070650A CN200810107065A CN101362820A CN 101362820 A CN101362820 A CN 101362820A CN A2008101070650 A CNA2008101070650 A CN A2008101070650A CN 200810107065 A CN200810107065 A CN 200810107065A CN 101362820 A CN101362820 A CN 101362820A
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Abstract
The invention discloses a blue hyperbranched polymer electroluminescent material with a pyrazoline unit core and a preparation method thereof, wherein, the hyperbranched polymer electroluminescent material is characterized by a chemical structural formula as shown on the right. The hyperbranched polymer electroluminescent material has the advantages that: 1. the hyperbranched polymer electroluminescent material can emit pure blue light, thereby overcoming the defect that exciplex is generated by incident primary chain cluster of the linear poly (9,9-dihexylfluorene) blue-light emitting materials; 2. The hyperbranched polymer electroluminescent material can apply to electroluminescent components, organic field effect transistors, solar batteries and biosensors.
Description
Technical field
The present invention relates to a kind of electroluminescent material and preparation method thereof, relating in particular to a kind of is the blue hyper-branched polymer electroluminescent materials and preparation method thereof of nuclear with the pyrazoline unit.
Background technology
Since first electroluminescent devices of report such as nineteen ninety Burroughes based on conjugated polymers, conjugated polymers is because its potential can be used for ultra-thin, flexible, big area, colored demonstration, and on element manufacturing, have advantages such as simple to operate, cheapness, become the focus of present flat pannel display area research.Present one synthesizes the electroluminescent material that polystyrene supports, multiclass such as poly-fluorenes, Polythiophene and derivative thereof cover a plurality of colors, excellent property.Green electroluminescent material is near practicability at present, and blue light and red light material are also having a certain distance aspect efficient, purity of color and life-span.Poly alkyl fluorene is considered to the industrialized blue polymer electroluminescent material of the easiest realization at present, but poly-fluorenes exists main chain easily to be assembled and the formation exciplex, cause the emission wavelength of device to move, thereby reduce the efficient and the illuminant colour purity of device to the long wave direction.In recent years, hyperbranched polymer more and more receives publicity.Because its specific molecule structure and chemical physics performance, be applied to many fields, even develop into field of photovoltaic materials such as electroluminescent.This base polymer can be divided into centronucleus, highly branched post and outermost layer group, can carry out independent regulation and control to Drawing abillity, electricity and optical property etc. by the modification of different piece like this.Consider the fatal problem that poly alkyl fluorene class blue emitting material exists, highly branched and topological framework improves the stability and the efficient of poly alkyl fluorene class material in conjunction with hyperbranched polymer in the present invention, and the current carrier that the modification by centronucleus improves polymer materials injects and transmission performance.
Summary of the invention
The object of the present invention is to provide a kind of is the blue hyper-branched polymer electroluminescent materials and preparation method thereof of nuclear with the pyrazoline unit, this luminescent material has not only kept poly-fluorenes hyperfluorescence and electroluminescent properties, also improve it and easily formed the shortcoming of exciplex, improve its purity of color greatly, improved the efficient of electroluminescent device.
The present invention is achieved like this, and it is characterized in that chemical structural formula is as follows:
Wherein, Ar1=
In the formula, R is H, C
nH
2n+1, OC
nH
2n+1, n=1-20,
Ar2＝
In the formula, R is H, C
nH2
N+1, OC
nH
2n+1, n=1-20,
Preferential n=4-12
Hyperbranched polymer a=2-60 of the present invention, b=2-60, c=2-60, further preferred a=20-40, b=20-40, c=20-40, M
n=5000-30000.
Preparation method's processing step of the present invention is: it is characterized in that in containing the organic solvent of mineral alkali as catalyzer, what have following structural formula contains pyrazoline ring monomer with organic palladium
In the formula, X=Cl, Br,
The aromatic series dihalide monomer following with molecular formula
Or
In the formula, X=Cl, Br,
And the following aromatic series hypoboric acid ester comonomer of molecular formula
Reaction makes.
Wherein R is H, C
nH
2n+1, OC
nH
2n+1, n=1-20,
The mol ratio that contains pyrazoline ring monomer, aromatic series dihalide monomer and aromatic series hypoboric acid ester comonomer among the present invention is: 1:2-20:3.5-21.5, reaction made in 48-100 hour under 60-150 ℃.
Organic solvent among the present invention is: tetrahydrofuran (THF), benzene, toluene, chlorobenzene;
Organic palladium catalyzer among the present invention is: palladium, Pd (PPh
3)
4, Pd
2(dba)
3
Mineral alkali among the present invention is: potassium hydroxide, sodium hydroxide, cesium hydroxide, salt of wormwood, yellow soda ash, cesium carbonate.
Any molecular structure that is provided can be provided for Ar1 base among the present invention, Ar2 base and R base.
Being prepared as of electroluminescent device among the present invention: it is characterized in that surface sputtering the conductive glass (ito glass) of indium oxide layer tin film after ultrasonic cleaner cleans, use oxygen plasma treatment, the hole injection layer polymkeric substance is for referring to poly-3,4-ethene dioxythiophene/polystyrolsulfon acid conductive polymers (PEDOT), luminescent layer is a polymkeric substance of the present invention, electron transfer layer is 1,3,5-three (1-phenyl-benzoglyoxaline) benzene (TPBI) and Alq3, cathode electrode Mg/Ag, hole injection layer and luminescent layer all adopt the mode of spin coating to make, surface sputtering apply forward bias between the conductive glass of indium oxide layer tin film and metal electrode, send pure blue light.
Advantage of the present invention is: 1, can be used as the pure blue light of emission, avoided linear poly alkyl fluorene class blue light material that main chain easily takes place effectively and assembled and the defective of formation exciplex; 2, can in electroluminescent device, organic field effect tube, solar cell and biosensor, obtain to use.
Embodiment
Each structural formula and pairing code name 1,2,3,4, PFZ10, PFZ20, PFNZ10 and PFNZ20 are expressed as follows in the following example:
Embodiment one is: structural formula 1 synthetic
In 50 milliliters of three-necked bottles, add sodium hydroxide solution, 0.93 gram (4.67 mmole) parabromoacetophenone, 1.70 gram (4.67 mmoles) 3 of 0.78 milliliter of 6.85 mol, 5-two bromo-4-hexyloxy phenyl aldehydes and 17 milliliters of ethanol form mixing solutions.After reaction mixture at room temperature stirred 5 hours, filter, precipitation is washed respectively with pure water, methyl alcohol.Head product recrystallization in ethanol gets pure product, productive rate 83%.
1HNMR(CDCl
3，300MH
z，δ/ppm)：7.90-7.87(d，2H，Ar-H)，7.77(s，1H，CO-C＝CH)，7.67-7.61(m，3H，Ar-H)，7.40(s，1H，CO-CH＝C)，4.07-4.03(t，2H，O-CH
2)，1.94-0.90(m，11H，CH
2?and?CH
3).
Embodiment two is: structural formula 2 synthetic
In 50 milliliters of round-bottomed flasks, add 1.71 gram (3.13 mmole) intermediates, 1,0.34 gram (3.13 mmole) phenylhydrazine and 12 milliliters of ethylene glycol monoethyl ethers.Reaction mixture is cooled to room temperature in reflux under the argon shield after 3 hours.Filter, precipitation washes with water, oven dry.Head product recrystallization in ethanol gets pure product, productive rate 85%.
1H?NMR(CDCl
3，300MH
z，δ/ppm)：7.58-7.49(m，4H，Ar-H)，7.45(s，1H，Ar-H)，7.25-7.19(t，2H，Ar-H)，7.04-7.02(d，2H，Ar-H)，6.87-6.83(t，1H，Ar-H)，5.18-5.12(m，1H，pyrazoline?ring?CH)，4.00-3.96(t，2H，O-CH
2)，3.85-3.75(m，1H，pyrazoline?ring?CH
2)，3.11-3.03(m，1H，pyrazoline?ring?CH
2)，1.90-0.88(m，11H，CH
2?and?CH
3).
Embodiment three is: structural formula 3 synthetic
In 50 milliliters of three-necked bottles, sodium hydroxide solution, 0.93 gram (4.67 mmole) parabromoacetophenone, 2.01 gram (4.67 mmole) 4-two para-bromoaniline benzaldehydes and 17 milliliters of ethanol of adding 0.78 milliliter of 6.85 mol form mixing solutions.After reaction mixture at room temperature stirred 5 hours, filter, precipitation is washed respectively with pure water, methyl alcohol.Head product recrystallization in ethanol gets pure product, productive rate 80%.
1H?NMR(CDCl
3，300MHz，δ/ppm)：7.86-7.85(d，2H)，7.78-7.73(d，1H，CO-C＝CH)，7.65-7.62(d，2H，Ar-H)，7.52-7.49(d，2H，Ar-H)，7.43-7.37(m，4H，Ar-H)，7.32(s，1H，CO-CH＝C)，7.04-6.97(m，6H，Ar-H).
Embodiment four is: structural formula 4 synthetic
In 50 milliliters of round-bottomed flasks, add 1.92 gram (3.13 mmole) intermediates, 3,0.34 gram (3.13 mmole) phenylhydrazine and 12 milliliters of ethylene glycol monoethyl ethers.Reaction mixture is cooled to room temperature in reflux under the argon shield after 3 hours.Filter, precipitation washes with water, oven dry.Head product recrystallization in ethanol gets pure product, productive rate 87%.
1H?NMR(CDCl
3，300MHz，δ/ppm)：7.59-7.57(d，2H，Ar-H)，7.52-7.49(d，2H，Ar-H)，7.34-7.30(d，4H，Ar-H)，7.23-7.17(m，4H，Ar-H)，7.09-7.07(d，2H，Ar-H)，7.00-6.97(d，2H，Ar-H)，6.93-6.89(d，4H，Ar-H)，6.84-6.80(t，1H，Ar-H)，5.27-5.21(m，1H，pyrazolinering?CH)，3.85-3.73(m，1H，pyrazoline?ring?CH
2)，3.16-3.08(m，1H，pyrazolinering?CH
2).
Embodiment five is: structural formula PFZ10's is synthetic
In 50 milliliters of round-bottomed flasks, add 502.31 milligrams of (1 mmoles) 9,9-dihexyl-2,7-hypoboric acid propylene glycol ester group fluorenes, 428.12 milligrams of (0.87 mmoles) 2,7-two bromo-9,9-dihexyl fluorenes, 2,22.5 milligrams of (0.019 mmole) Pd (PPh of 55.24 milligrams of (0.087 mmole) intermediates
3)
4, 15 milliliters of toluene and 5 milliliters of 2M solution of potassium carbonate.At 85-90 ℃, vigorous stirring is 60 hours under the argon shield with reaction mixture.The question response mixture is cooled to room temperature, pour the mixture (volume ratio is 10:1) of 200 ml methanol and water into, get fibrous solid, suction filtration, with methyl alcohol and this solid of water washing repeatedly, the gained solid gets the yellow-green colour solid with acetone repetitive scrubbing in cable type extractor according, and it is 81%.1H NMR (CDCl that vacuum-drying makes polymer P FZ10. productive rate
3, 300MHz, δ/ppm): 7.85-7.76 (m, broad, Ar-H), 7.70-7.57 (m, broad, Ar-H), 7.51-7.46 (m, broad, Ar-H), 7.39-7.34 (m, broad, Ar-H), 5.21-5.16 (m, pyrazoline ring CH), 4.02-3.98 (t, O-CH
2), 3.87-3.79 (m, pyrazoline ring CH
2), 3.18-3.09 (m, pyrazoline ring CH
2), 2.10 (s, broad, fluorene ring CH), 1.13 (s, broad, CH
2), 0.79-0.75 (t, broad, CH
2And CH
3).
Embodiment six is: structural formula PFZ20's is synthetic
In 50 milliliters of round-bottomed flasks, add 502.31 milligrams of (1 mmoles) 9,9-dihexyl-2,7-hypoboric acid propylene glycol ester group fluorenes, 457.99 milligrams of (0.93 mmoles) 2,7-two bromo-9,9-dihexyl fluorenes, 2,22.5 milligrams of (0.019 mmole) Pd (PPh of 29.55 milligrams of (0.047 mmole) intermediates
3)
4, 15 milliliters of toluene and 5 milliliters of 2M solution of potassium carbonate.At 85-90 ℃, vigorous stirring is 60 hours under the argon shield with reaction mixture.The question response mixture is cooled to room temperature, pour the mixture (volume ratio is 10:1) of 200 ml methanol and water into, get fibrous solid, suction filtration, with methyl alcohol and this solid of water washing repeatedly, the gained solid gets the yellow-green colour solid with acetone repetitive scrubbing in cable type extractor according, and vacuum-drying makes polymer P FZ20, productive rate 84%.
1H?NMR(CDCl
3，300MHz，δ/ppm)：7.87-7.77(m，broad，Ar-H)，7.72-7.58(m，broad，Ar-H)，7.52-7.47(m，broad，Ar-H)，7.40-7.35(m，broad，Ar-H)，5.19-5.15(m，pyrazoline?ring?CH)，4.00-3.96(t，O-CH
2)，3.85-3.76(m，pyrazoline?ring?CH
2)，3.15-3.07(m，pyrazoline?ring?CH
2)，2.12(s，broad，fluorene，CH
2)，1.15(s，broad，CH
2)，0.81-0.76(t，broad，CH
2andCH
3).
Embodiment seven is: structural formula PFNZ10's is synthetic
In 50 milliliters of round-bottomed flasks, add 502.31 milligrams of (1 mmoles) 9,9-dihexyl-2,7-hypoboric acid propylene glycol ester group fluorenes, 428.12 milligrams of (0.87 mmoles) 2,7-two bromo-9,9-dihexyl fluorenes, 4,22.5 milligrams of (0.019 mmole) Pd (PPh of 60.98 milligrams of (0.087 mmole) intermediates
3)
4, 15 milliliters of toluene and 5 milliliters of 2M solution of potassium carbonate.At 85-90 ℃, vigorous stirring is 60 hours under the argon shield with reaction mixture.The question response mixture is cooled to room temperature, pour the mixture (volume ratio is 10:1) of 200 ml methanol and water into, get fibrous solid, suction filtration, with methyl alcohol and this solid of water washing repeatedly, the gained solid gets the yellow-green colour solid with acetone repetitive scrubbing in cable type extractor according, and vacuum-drying makes polymer P FNZ10, productive rate 78%.
1H?NMR(CDCl
3，300MHz，δ/ppm)：7.85-7.82(m，broad，Ar-H)，7.71-7.57(m，broad，Ar-H)，7.49-7.46(m，broad，Ar-H)，7.37-7.34(m，broad，Ar-H)，5.31-5.24(m，pyrazoline?ring?CH)，3.87-3.75(m，pyrazoline?ring?CH
2)，3.18-3.11(m，pyrazoline?ring?CH
2)，2.11(s，broad，fluorene，CH
2)，1.13(s，broad，CH
2)，0.79-0.77(t，broad，CH
2?and?CH
3).
Embodiment eight is: structural formula PFNZ20's is synthetic
In 50 milliliters of round-bottomed flasks, add 502.31 milligrams of (1 mmoles) 9,9-dihexyl-2,7-hypoboric acid propylene glycol ester group fluorenes, 457.99 milligrams of (0.93 mmoles) 2,7-two bromo-9,9-dihexyl fluorenes, 4,22.5 milligrams of (0.019 mmole) Pd (PPh of 32.62 milligrams of (0.047 mmole) intermediates
3)
4, 15 milliliters of toluene and 5 milliliters of 2M solution of potassium carbonate.At 85-90 ℃, vigorous stirring is 60 hours under the argon shield with reaction mixture.The question response mixture is cooled to room temperature, pour the mixture (volume ratio is 10:1) of 200 ml methanol and water into, get fibrous solid, suction filtration, with methyl alcohol and this solid of water washing repeatedly, the gained solid gets the yellow-green colour solid with acetone repetitive scrubbing in cable type extractor according, and vacuum-drying makes polymer P FNZ20 synthetic method with reference to embodiment 5, productive rate 82%.
1H?NMR(CDCl
3，300MHz，δ/ppm)：7.85-7.80(m，broad)，7.76-7.57(m，broad)，7.51-7.46(m，broad)，7.39-7.34(m，broad)，5.30-5.25(m，pyrazoline?ring?CH)，3.88-3.77(m，pyrazoline?ring?CH
2)，3.16-3.08(m，pyrazoline?ring?CH
2)，2.10(s，broad，fluorene，CH
2)，1.13(s，broad，CH
2)，0.79-0.75(t，broad，CH
2?and?CH
3).
Embodiment nine is: the preparation of electroluminescent device and sign
Ito glass is after ultrasonic cleaner cleans, use oxygen plasma treatment, the square resistance of ito glass is 30 Ω, and the hole injection layer polymkeric substance is PEDOT, and luminescent layer is a polymkeric substance of the present invention, electron transfer layer is TPBI and Alq3, cathode electrode Mg:Ag (10:1), hole injection layer and luminescent layer all adopt the mode of spin coating to make, and apply forward bias between ITO and metal electrode, send pure blue light, it is as shown in the table for luminescent properties.
| Device architecture | Maximum emission wavelength (nm) | Open bright voltage (V) | External quantum efficiency (%) |
| ITO/PEDOT/PFZ10/TPBI/Alq 3/Mg:Ag | 456 | 5.5 | 1.33 |
| ITO/PEDOT/PFZ20/TPBI/Alq 3/Mg:Ag | 453 | 6.0 | 0.92 |
| ITO/PEDOT/PFNZ10/TPBI/Alq 3/Mg:Ag | 458 | 5.3 | 1.93 |
| ITO/PEDOT/PFNZ20/TPBI/Alq 3/Mg:Ag | 455 | 6.3 | 1.40 |
Claims (8)
1, a kind of is the blue hyper-branched polymer electroluminescent materials and preparation method thereof of nuclear with the pyrazoline unit, it is characterized in that chemical structural formula is as follows:
Wherein, Ar1=
In the formula, R is H, C
nH
2n+1, OC
nH
2n+1, n=1-20,
Ar2＝
In the formula, R is H, C
nH
2n+1, OC
nH
2n+1, n=1-20,
Preferential n=4-12
Described hyperbranched polymer a=2-60, b=2-60, c=2-60, further preferred a=20-40, b=20-40, c=20-40, M
n=5000-30000.
2, a kind of claim 1 is described is blue hyper-branched polymer electroluminescent materials of nuclear and preparation method thereof with the pyrazoline unit, it is characterized in that the processing method step is: in containing the organic solvent of mineral alkali, as catalyzer, what have following structural formula contains pyrazoline ring monomer with organic palladium
In the formula, X=Cl, Br,
The aromatic series dihalide monomer following with molecular formula
Or
In the formula, X=Cl, Br,
And the following aromatic series hypoboric acid ester comonomer of molecular formula
Or
Reaction makes,
Wherein R is H, C
nH
2n+1, OC
nH
2n+1, n=1-20.
3, according to claim 2 is the blue hyper-branched polymer electroluminescent materials and preparation method thereof of nuclear with the pyrazoline unit, it is characterized in that the mol ratio that contains pyrazoline ring monomer, aromatic series dihalide monomer and aromatic series hypoboric acid ester comonomer is: 1:2-20:3.5-21.5, reaction made in 48-100 hour under 60-150 ℃.
4, according to claim 2 is the blue hyper-branched polymer electroluminescent materials and preparation method thereof of nuclear with the pyrazoline unit, it is characterized in that organic solvent is: tetrahydrofuran (THF), benzene, toluene, chlorobenzene.
5, according to claim 2 is the blue hyper-branched polymer electroluminescent materials and preparation method thereof of nuclear with the pyrazoline unit, it is characterized in that the organic palladium catalyzer is: palladium, Pd (PPh
3)
4, Pd
2(dba)
3
6, according to claim 2 is the blue hyper-branched polymer electroluminescent materials and preparation method thereof of nuclear with the pyrazoline unit, it is characterized in that mineral alkali is: potassium hydroxide, sodium hydroxide, cesium hydroxide, salt of wormwood, yellow soda ash, cesium carbonate.
7, described according to claim 1 to 6 is the blue hyper-branched polymer electroluminescent materials and preparation method thereof of nuclear with the pyrazoline unit, it is characterized in that any molecular structure that is provided can be provided for Ar1 base, Ar2 base and R base.
8, according to claim 1 is the blue hyper-branched polymer electroluminescent materials and preparation method thereof of nuclear with the pyrazoline unit, it is characterized in that being prepared as of electroluminescent device among the present invention: surface sputtering the conductive glass of indium oxide layer tin film after ultrasonic cleaner cleans, use oxygen plasma treatment, the hole injection layer polymkeric substance is for referring to poly-3,4-ethene dioxythiophene/polystyrolsulfon acid conductive polymers, luminescent layer is a polymkeric substance of the present invention, electron transfer layer is 1,3,5-three (1-phenyl-benzoglyoxaline) benzene and Alq3, cathode electrode Mg/Ag, hole injection layer and luminescent layer all adopt the mode of spin coating to make, surface sputtering apply forward bias between the conductive glass of indium oxide layer tin film and metal electrode, send pure blue light.
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|---|---|---|---|
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|---|---|---|---|
| CNA2008101070650A CN101362820A (en) | 2008-09-04 | 2008-09-04 | Blue hyper-branched polymer electroluminescent materials using pyrazoline unit as nuclear and preparation method thereof |
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ID=40389440
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| CN105037712A (en) * | 2015-06-23 | 2015-11-11 | 内江师范学院 | Organic blue-fluorescent material and preparation method thereof |
| JP2016017160A (en) * | 2014-07-10 | 2016-02-01 | 東洋紡株式会社 | Composite polymer electrolyte film, method for producing the same and application thereof |
| CN114591241A (en) * | 2022-03-14 | 2022-06-07 | 内蒙古扬帆新材料有限公司 | Intramolecular sensitization macromolecule photoinitiator containing pyrazoline and alpha-aminoketone, and preparation method and application thereof |
| CN115368668A (en) * | 2022-09-15 | 2022-11-22 | 山东海科创新研究院有限公司 | Modified EVOH resin and preparation method thereof |
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2008
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016017160A (en) * | 2014-07-10 | 2016-02-01 | 東洋紡株式会社 | Composite polymer electrolyte film, method for producing the same and application thereof |
| CN105037712A (en) * | 2015-06-23 | 2015-11-11 | 内江师范学院 | Organic blue-fluorescent material and preparation method thereof |
| CN105037712B (en) * | 2015-06-23 | 2017-05-10 | 内江师范学院 | Organic blue-fluorescent material and preparation method thereof |
| CN114591241A (en) * | 2022-03-14 | 2022-06-07 | 内蒙古扬帆新材料有限公司 | Intramolecular sensitization macromolecule photoinitiator containing pyrazoline and alpha-aminoketone, and preparation method and application thereof |
| CN114591241B (en) * | 2022-03-14 | 2024-02-13 | 内蒙古扬帆新材料有限公司 | Intramolecular sensitized macromolecular photoinitiator containing pyrazoline and alpha-amino ketone and preparation method and application thereof |
| CN115368668A (en) * | 2022-09-15 | 2022-11-22 | 山东海科创新研究院有限公司 | Modified EVOH resin and preparation method thereof |
| CN115368668B (en) * | 2022-09-15 | 2023-07-21 | 山东海科创新研究院有限公司 | Modified EVOH resin and preparation method thereof |
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