CN101041773B - Organic photoelectric polymer and usage thereof - Google Patents
Organic photoelectric polymer and usage thereof Download PDFInfo
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- CN101041773B CN101041773B CN2006100585773A CN200610058577A CN101041773B CN 101041773 B CN101041773 B CN 101041773B CN 2006100585773 A CN2006100585773 A CN 2006100585773A CN 200610058577 A CN200610058577 A CN 200610058577A CN 101041773 B CN101041773 B CN 101041773B
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- organic photoelectric
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- 229920000642 polymer Polymers 0.000 title claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000000463 material Substances 0.000 abstract description 20
- 238000000034 method Methods 0.000 description 30
- 150000002220 fluorenes Chemical class 0.000 description 25
- 239000000178 monomer Substances 0.000 description 22
- 239000000126 substance Substances 0.000 description 17
- 239000003999 initiator Substances 0.000 description 14
- 238000006116 polymerization reaction Methods 0.000 description 14
- 229920001059 synthetic polymer Polymers 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- 238000001194 electroluminescence spectrum Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- -1 aryl Grignard reagent Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 description 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- AVXFJPFSWLMKSG-UHFFFAOYSA-N 2,7-dibromo-9h-fluorene Chemical class BrC1=CC=C2C3=CC=C(Br)C=C3CC2=C1 AVXFJPFSWLMKSG-UHFFFAOYSA-N 0.000 description 1
- KCOYLRXCNKJSSC-UHFFFAOYSA-N 9h-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 KCOYLRXCNKJSSC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000006210 cyclodehydration reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
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- Electroluminescent Light Sources (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Abstract
The invention discloses a structured organic photoelectric polymer formula (1), which can be used to luminescent layer of organic light-emitting component as blue light material.
Description
Technical field
The present invention relates to a kind of organic photoelectrical material, it can be used for the luminescent layer of organic illuminating element, as blue light material.
Background technology
(Organic Light Emitting Diode OLED) was delivered by Kodak as far back as 1987 Organic Light Emitting Diode, was that a kind of luminous organic material self emitting characteristics of utilizing is to reach the display element of display effect.It is made of a pair of electrodes and an organic luminous layer, wherein, contains luminescent material in this organic luminous layer.Between electric current is by transparent anode and metallic cathode, electronics and electric hole can be in luminescent material in conjunction with and when producing exciton, just can make luminescent material produce the effect of giving out light.
The blue light material of fluorenes thing (Fluorenes) the Chang Zuowei Organic Light Emitting Diode of the following chemical structure of tool:
Its major cause is: find in (1) research of document formerly that the fluorescent radiation wavelength of poly-fluorenes thing (Polyfluorenes) contains 400～460nm (blue light), and (Chemical Stability) is all relatively good for thermostability (Thermal Stability), chemical stability, therefore is well suited for the main body as organic blue light emitting body; (2) though poly-fluorenes thing at solution state or solid-state (Solid-State), its fluorescence quantum yield (Fluorescence Quantum Yield) all relatively good (60～80%) is so can have luminous efficiency preferably when being used for luminous element.
Even so, in the process of development, find that poly-fluorenes thing has the situation of piling up to take place easily, reduces its element luminous efficiency.Therefore the present invention proposes a kind of fluorenes thing (Chiral Fluorene) macromolecular material with asymmetric center, can effectively avoid fluorenes thing stack-up issue to take place.
Summary of the invention
The object of the present invention is to provide a kind of organic photoelectric polymer, can be used as the organic light emission layer material, and have good illumination efficiency.
Organic photoelectric polymer of the present invention is a kind of macromolecular material with asymmetric center fluorenes thing (Chiral Fluorene), and it has following structural formula (I):
Wherein,
n
1, n
2And n
4It respectively is integer greater than 1;
n
3Be 0 or greater than 1 integer;
X and Y are the C that is substituted or is unsubstituted
4-C
60Aromatic series unit or aliphatics unit; With
G
1, G
2, G
3And G
4Respectively be the C that is substituted or is unsubstituted
2-C
40Aromatic series base or fatty group;
G wherein
1And G
2Inequality, and work as n
3Be not 0 o'clock, X and Y are inequality and work as n
3Be 0 o'clock, X is not equal to
Description of drawings
Fig. 1 represents the EL spectrum that records in the element of long-time (120 ℃, the 24 hours) made of high temperature.
Fig. 2 represents the EL spectrum that records in the element of low temperature short period of time (100 ℃, 30 minutes) made.
Embodiment
The present invention avoids the fluorenes thing situation of piling up to take place for improving the element luminous efficiency, reaching, and has selected to connect G in No. 9 positions of fluorenes thing
1With G
2Two substituting groups inequality, and in the high molecular polymerization process, connect the group inequality of X and Y respectively in No. 2 positions of fluorenes thing and No. 7 positions, make the carbon atom of No. 9 positions become an asymmetric center (ChiralCenter), so the polymkeric substance of synthetic gained may also may be the S-configuration for the R-configuration, and when successively bringing R-configuration or S-configuration structure respectively into because of bond on the whole macromolecular chain, each macromolecular chain relatively is not easy to produce and piles up phenomenon because of structural difference.
The present invention has in formula (I) polymkeric substance of at least one asymmetric center, n
1, n
2And n
4Be preferably 1 to 300 integer, n
3It is 0 or 1 to 300 integer; X and Y be the C for being substituted or being unsubstituted respectively
6-C
40Aromatic series unit or aliphatics unit; And G
1, G
2, G
3And G
4Respectively be the C that is substituted or is unsubstituted
6-C
30Aromatic series base or fatty group, but G
1And G
2Inequality.
According to of the present invention one preferred specific embodiment, in the above-mentioned formula (I), work as n
3Be not 0 o'clock, X and Y are C
6-C
40-aromatic series unit, but both are inequality; And, work as n according to another preferred specific embodiment of the present invention
3Be 0, X is C
6-C
40-aromatic series unit, but X is not:
According to an advantageous embodiment of the invention, X and Y there is no particular restriction, and it is such as but not limited to following aromatic series unit:
In the following formula, each R represents C respectively
1-C
16Alkyl or C
1-C
16Alkoxyl group and r are 0,1,2 or 3; And G
1, G
2, G
3And G
4Respectively be the C that is substituted or is unsubstituted
6-C
30-aromatic group is preferably phenyl or through C
1-C
16-alkyl (is preferably C
1-C
10-alkyl) or C
1-C
16-alkoxyl group (is preferably C
1-C
10-alkyl) single, two or trisubstd phenyl.
The molecular-weight average of formula of the present invention (I) polymkeric substance, approximately between 30,000 to 3,000, between 000, preferably between about 50,000 to 1,200, the molecular-weight average between 000.
Formula of the present invention (I) organic photoelectric polymer can be used in the organic light-emitting diode element, as the luminescent layer material.Polymkeric substance of the present invention can be incorporated in the organic light-emitting diode element as luminescent layer material or luminescent layer part material by well-known method in any this technology.In other words, material of the present invention can with other material with different ratio blending after, coat again on the element, together as the luminescent layer material.The luminescent layer material that contains luminous organic material of the present invention has the character of emission blue light, represents good illumination efficiency simultaneously.
Simultaneously, the technician who is familiar with organic light-emitting diode element understands, if luminescent layer is done luminous doping, for example cooperates (Doping) technology of doping, to have asymmetric center fluorenes object height molecular material is the luminescent layer material of main part, plays the part of energy supplier (Host) role; Or to have asymmetric center fluorenes object height molecular material be the luminous hotchpotch of object, plays the part of energy recipient (Guest) role, more can promote the luminous efficiency of organic light-emitting diode element and adjust luminous photochromic.
Following examples are used for that the invention will be further described, but non-in order to restriction protection scope of the present invention.Any those skilled in the art, modification that can realize easily and change all are contained in the scope of this case specification sheets disclosure.
The making of fluorene derivatives
No. 9 positions of fluorenes can be easy to be oxidized to ketone group, can make locational carbon ribbon part positive charge thus No. 9, next just can utilize Green's sodium reagent (aryl Grignard reagent) of aromatic base to connect aromatic base No. 9 positions, utilize Friedel-Crafts to be reflected at No. 9 positions again and connect second aromatic base, so just, can produce 9, the fluorenes intermediate (initiator 1 or initiator 2 or initiator 3 shown in flow process I) that 9-two aromatic bases replace.In addition, directly under alkaline condition, with 2,7-dibromo fluorenes and the reaction of 1-bromooctane can get initiator 4.(shown in flow process II)
Flow process I
Flow process II
The making of polymerization single polymerization monomer
Carbazole (Carbazole) can get initiator 5a and 5b with 1-bromo-4-tributyl benzene under the catalysis of metallic palladium, again with N-bromo-succinimide (N-Bromosuccinimide, NBS) carry out bromination, sub-polymerization single polymerization monomer 6a and 6b (shown in flow process III) can secure satisfactory grades.
Flow process III
In addition, utilize the bromine displacement of n-Butyl Lithium and initiator 1 after, connect the boron ester polymerization single polymerization monomer 7 (as flow process IV institute) that can secure satisfactory grades.
Flow process IV
In addition, under the catalysis of metallic palladium, with polymerization single polymerization monomer 7 and the reaction of 2-iodo-5-bromo pyrimi piperidine, sub-polymerization single polymerization monomer 8 (shown in flow process V) can secure satisfactory grades.
Flow process V
2-methyl-4-bromobenzene acyl chlorides and 3-methyl-4-bromobenzene acyl (or 3-bromo-4-methylbenzene hydrazides) are reacted under alkaline condition, again with POCl
3Cyclodehydration can secure satisfactory grades sub-polymerization single polymerization monomer 9a and 9b (shown in flow process VI).
Flow process VI
Macromolecular polymerization reaction
Initiator 2, monomer 6a are mixed with monomer 7, carry out the Suzuki coupled reaction, synthetic polymer P 1 (shown in flow process VII) with asymmetric center fluorenes thing, molecular weight is 42874, molecular weight looses more, and (Polydispersity is 1.77 PDI) to property.This polymkeric substance structurally, each molecular chain has different optical activity centers.
Flow process VII
Initiator 3, monomer 7 are mixed with monomer 8, carry out the Suzuki coupled reaction, synthetic polymer P 2 (shown in flow process VIII) with asymmetric center fluorenes thing, molecular weight is 44068, molecular weight looses more, and (Polydispersity is 1.89 PDI) to property.This polymkeric substance structurally, each molecular chain has different optical activity centers.
Flow process VIII
Initiator 3, monomer 6b are mixed with monomer 7, carry out the Suzuki coupled reaction, synthetic polymer P 3 (shown in flow process IX) with asymmetric center fluorenes thing, molecular weight is 89183, molecular weight looses more, and (Polydispersity is 2.03 PDI) to property.This polymkeric substance structurally, each molecular chain has different optical activity centers.
Flow process IX
Initiator 2, monomer 7 are mixed with monomer 8, carry out the Suzuki coupled reaction, synthetic polymer P 4 (shown in flow process X) with asymmetric center fluorenes thing, molecular weight is 81665, molecular weight looses more, and (Polydispersity is 2.05 PDI) to property.This polymkeric substance structurally, each molecular chain has different optical activity centers.
Flow process X
Initiator 6b, monomer 7 are mixed with monomer 4, carry out the Suzuki coupled reaction, synthetic polymer P 5 (shown in flow process XI) with asymmetric center fluorenes thing, molecular weight is 83405, molecular weight looses more, and (Polydispersity is 1.88 PDI) to property.This polymkeric substance structurally, each molecular chain has different optical activity centers.
Flow process XI
Initiator 2, monomer 9b are mixed with monomer 7, carry out the Suzuki coupled reaction, synthetic polymer P 6 (shown in flow process XII) with asymmetric center fluorenes thing, molecular weight is 35128, molecular weight looses more, and (Polydispersity is 1.64 PDI) to property.This polymkeric substance structurally, each molecular chain has different optical activity centers.
Flow process XII
Initiator 2, monomer 9a are mixed with monomer 7, carry out the Suzuki coupled reaction, synthetic polymer P 7 (shown in flow process XIII) with asymmetric center fluorenes thing, molecular weight is 33401, molecular weight looses more, and (Polydispersity is 1.58 PDI) to property.This polymkeric substance structurally, each molecular chain has different optical activity centers.
Flow process XIII
With initiator 2, monomer 9a, 9, the 10-dibromoanthracene mixes with monomer 7, carry out the Suzuki coupled reaction, synthetic polymer P 8 (shown in flow process XIV) with asymmetric center fluorenes thing, molecular weight is 197456, molecular weight looses more, and (Polydispersity is 2.18 PDI) to property.This polymkeric substance structurally, each molecular chain has different optical activity centers.
Flow process XIV
Asymmetric center fluorenes thing photophysical property
In toluene, concentration is made rotary coating with 500rpm to 3000rpm between 1% to 3% with institute's synthetic polymer dissolution, on the ito glass surface, forms film with polymer-coated, and at 5.0x10
-6Under the pressure of torr, with this film plated aluminum electrode, the voltage that imposes 3 volts to 20 volts drives, PR650 photometer with Kodak carries out electroluminescence spectrum (Electroluminescent spectrum) measurement, Fig. 1 and Fig. 2 represent respectively in long-time (120 ℃ of high temperature, 24 hours) and the EL spectrum that records of the element of low temperature short period of time (100 ℃, 30 minutes) made.
Polymer rerum natura table:
| Polymkeric substance | Mw | Mn | Mw/Mn | Maximum absorption wavelength (nm) | Maximum radiation wavelength (nm) |
| P1 | 42874 | 24130 | 1.77 | 389 | 421 |
| P2 | 44068 | 23346 | 1.89 | 388 | 421 |
| Polymkeric substance | Mw | Mn | Mw/Mn | Maximum absorption wavelength (nm) | Maximum radiation wavelength (nm) |
| P3 | 89183 | 39833 | 2.03 | 386 | 420 |
| P4 | 81665 | 39833 | 2.05 | 390 | 421 |
| P5 | 83405 | 44280 | 1.88 | 387 | 419 |
| P6 | 35128 | 21468 | 1.64 | 386 | 424 |
| P7 | 33401 | 21117 | 1.58 | 385 | 424 |
| P8 | 197456 | 90466 | 2.18 | 389 | 446 |
Annotate: absorb with the radioactive wave long data be that polymer is dissolved in the chloroform and records.
Find from the data of Fig. 1 and Fig. 2, through long-time (120 ℃ of high temperature, 24 hours) the element of macromolecule membrane made after the heating, with (100 ℃ of low temperature short period of time, 30 minutes) element made of heating, there is no obvious difference, learn that therefore the asymmetric center of importing has been brought into play the effect of avoiding macromolecular chain to pile up really in the present invention.
Claims (6)
1. organic photoelectric polymer with following structural formula (I), its molecular-weight average is between 30,000 to 3,000, between 000:
Wherein,
n
1, n
2And n
4It respectively is integer greater than 1;
n
3Be 0 or greater than 1 integer;
X, Y are the groups that independently is selected from by in the following group that constitutes:
Wherein, each R represents C respectively
1-C
16Alkyl or C
1-C
16Alkoxyl group and r are 0,1,2 or 3; With
G
1, G
2, G
3And G
4It respectively is phenyl or through C
1-C
16Alkyl or C
1--C
16Alkoxyl group list, two or trisubstd phenyl;
G wherein
1And G
2Inequality, and work as n
3Be not 0 o'clock, X and Y are inequality and work as n
3Be 0 o'clock, X is not
2. organic photoelectric polymer according to claim 1, it has at least one asymmetric center.
3. organic photoelectric polymer according to claim 1, wherein n
1, n
2And n
4It respectively is integer greater than 1 to 300; n
3Be 0 or greater than 1 to 300 integer.
4. organic photoelectric polymer according to claim 1, wherein n
3Be 0.
5. organic photoelectric polymer according to claim 1, its molecular-weight average is between 40,000 to 1,200, between 000.
6. luminescent layer that is used for organic illuminating element, it comprises organic photoelectric polymer according to claim 1.
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|---|---|---|---|
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Applications Claiming Priority (1)
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|---|---|---|---|
| CN2006100585773A CN101041773B (en) | 2006-03-22 | 2006-03-22 | Organic photoelectric polymer and usage thereof |
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| CN101041773B true CN101041773B (en) | 2010-06-16 |
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