DPP-containing conjugated polymers and electroluminescent...

Details DPP-containing conjugated polymers and electroluminescent... DPP-containing conjugated polymers and electroluminescent...

2000-08-03

2002-09-17

Yamnitzky, Marie (Department: 1774)

Stock material or miscellaneous articles

Composite

Of inorganic material

C428S917000, C313S504000, C313S506000, C257S040000, C252S301350, C528S367000, C528S394000, C528S397000

Reexamination Certificate

active

06451459

ABSTRACT:

The present invention relates to diketopyrrolopyrrole (DPP) based polymers and copolymers comprising the following units
wherein x is chosen in the range of from 0.005 to 1, preferably from 0.01 to 1, and y from 0.995 to 0, preferably 0.99 to 0, and wherein x+y=1, and wherein Ar
1
and Ar
2
independently from each other stand for
 and m, n being numbers from 1 to 10, and
R
1
and R
2
independently from each other stand for H, C
1
-C
18
alkyl, —C(O)O—C
1
-C
18
alkyl, perfluoro-C
1
-C
12
alkyl, unsubstituted C
6
-C
12
aryl or one to three times with C
1
-C
12
alkyl, C
1
-C
12
alkoxy, or halogen substituted C
6
-C
12
aryl, C
1
-C
12
alkyl-C
6
-C
12
aryl, or C
6
-C
12
aryl-C
1
-C
12
alkyl,
R
3
and R
4
preferably stand for hydrogen, C
1
-C
12
alkyl, C
1
-C
12
alkoxy, unsubstituted C
6
-C
12
aryl or one to three times with C
1
-C
12
alkyl, C
1
-C
12
alkoxy, or halogen substituted C
6
-C
12
aryl or perfluoro-C
1
-C
12
alkyl, and
R
5
preferably stands for C
1
-C
12
alkyl, C
1
-C
12
alkoxy, unsubstituted C
6
-C
12
aryl or one to three times with C
1
-C
12
alkyl, C
1
-C
12
alkoxy, or halogen substituted C
6
-C
12
aryl, or perfluoro-C
1
-C
12
alkyl,
blends of such polymers and copolymers with other polymers, their use for the preparation of electroluminescent (“EL”) devices and EL devices comprising such polymers or copolymers.
EP-A 787,730 describes a polyacrylate and a polyurethane obtained by the polymerization of a DPP of formula Ia
wherein Q
1
and Q
4
independently of each other stand for a polymerizable reactive group, and Q
2
and Q
3
independently of each other stand for hydrogen, C
12
-C
24
alkyl, C
6
-C
24
alkyl which is interrupted one or more times by O or S, or are a group of the formula
 in which Q
5
is C
4
-C
18
alkyl or C
5
-C
10
cycloalkyl.
Though it is mentioned that compounds Ia can be used for the preparation of photo- and electroconductive polymers, no corresponding examples are given. Further, no teaching is given of how to prepare EL devices comprising DPP-based polymers and of how to select the appropriate DPP-monomers resp. DPP-polymers.
Macromol. Chem. Phys. 200 (1999) 106-112 describes fluorescent DPP-polymers obtainable by the copolymerization of bifunctional monomeric DPP-derivatives, wherein the functional groups are attached to the N-atoms of the DPP-molecule, with diisocyanates or di-ols or di-acids. No teaching is given whether the described polymers can be used in EL devices.
JACS 115 (1993) 11735-11743 describes DPP-polymers demonstrating photorefractivity, i.e. exhibiting photoconductivity and second order non-linear-optical activity. Although the photoconductive properties are measured using a device similar to an EL device, i.e. irradiating the device with a laser beam and then measuring the current resulting from this irradiation, no measurements were carried out with regard to electroluminescence. Further, no teaching is given of how to select other DPP-polymers.
Adv. Mater. 4 (1992) 36-37 describes poly(p-phenylene)-based EL devices emitting blue light. However, no teaching and no motivation are given of how to modify the used polymers. Further, &lgr;
max
of electroluminescence is in the blue region.
Hence, an object of the present invention was to provide novel DPP-based polymers and copolymers, preferably exhibiting a &lgr;
max
of electroluminescence which is not in the blue region, i.e. not between 400 to 470 nm, but preferably in the range of from 500 to 800, more preferably of from 600 to 750 nm, and its use in electronic and photonic devices such as diodes, light-emitting diodes, photodiodes, field-effect transistors, polymer grid triodes, light-emitting electrochemical cells, optocouplers, and lasers. Further, the intensity of the electroluminescence of the novel polymers should be improved with regard to poly(1,4-phenylene). In addition, the processability into thin films by spin-coating and solution coating of the novel polymers should be improved with regard to poly(1,4-phenylene).
Accordingly, the above-mentioned DPP-based polymers have been found.
In addition, blends comprising the inventive polymers, EL devices comprising the inventive polymers and the use of DPP I and its polymers have been found, too.
Preferably, Ar
1
stands for
Preferably, R
1
and R
2
independently from each other stand for H, C
1
-C
12
alkyl, —C(O)O—C
1
-C
12
alkyl, perfluoro-C
1
-C
12
alkyl, unsubstituted C
6
-C
12
aryl or one to three times with C
1
-C
12
alkyl, C
1
-C
12
alkoxy, or halogen substituted C
6
-C
12
aryl, C
1
-C
12
alkyl-C
6
-C
12
aryl, or C
6
-C
12
aryl-C
1
-C
12
alkyl,
R
3
and R
4
preferably stand for hydrogen, C
1
-C
12
alkyl, C
1
-C
12
alkoxy, unsubstituted C
6
-C
12
aryl or one to three times with C
1
-C
12
alkyl, C
1
-C
12
alkoxy, or halogen substituted C
6
-C
12
aryl or perfluoro-C
1
-C
12
alkyl, and
R
5
preferably stands for C
1
-C
12
alkyl, C
1
-C
12
alkoxy, unsubstituted C
6
-C
12
aryl or one to three times with C
1
-C
12
alkyl, C
1
-C
12
alkoxy, or halogen substituted C
6
-C
12
aryl, or perfluoro-C
1
-C
12
alkyl.
A preferred embodiment concerns a copolymer comprising the following units
wherein R
6
and R
7
, independently from each other, have the meaning of hydrogen, C
1
-C
12
alkyl, C
1
-C
12
alkoxy, unsubstituted C
6
-C
12
aryl or one to three times with C
1
-C
12
alkyl, C
1
-C
12
alkoxy, or halogen substituted C
6
-C
12
aryl or perfluoro-C
1
-C
12
alkyl, more preferably
 C
1
-C
18
alkyl stands for methyl, ethyl, n-, i-propyl, n-, i-, sec.-, tert.-butyl, n-, i-, neo-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, 3,7-dimethyloctyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, preferably for C
1
-C
12
alkyl such as methyl, ethyl, n-, i-propyl, n-, i-, sec.-, tert.-butyl, n-, i-, neo-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, 3,7-dimethyloctyl, n-undecyl, or n-dodecyl.
perfluoro-C
1
-C
12
alkyl stands for fully or partially fluorinated C
1
-C
12
alkyl such as fluoromethyl, trifluoromethyl, pentafluoroethyl, heptafluoropropyl, or nonafluorobutyl.
C
1
-C
12
alkoxy stands for methoxy, ethoxy, n-, i-propoxy, n-, i-, sec.- or tert.-butoxy, n-, i-pentoxy, n-hexoxy, n-heptoxy-, n-octoxy, 2-ethylhexoxy, n-nonoxy, n-decoxy, 3,7-dimethyloctoxy, n-undecoxy, n-dodecoxy, preferably for C
4
-C
12
alkoxy such as n-, i-, sec.- or tert.-butoxy, n-, i-pentoxy, n-hexoxy, n-heptoxy-, n-octoxy, 2-ethylhexoxy, n-nonoxy, n-decoxy, 3,7-dimethyloctoxy, n-undecoxy, n-dodecoxy.
C
6
-C
12
aryl is typically phenyl, 1-naphthyl, 2-naphthyl, or 4-biphenyl.
C
1
-C
12
alkyl-C
6
-C
12
aryl stands for e.g. 2-, 3-, 4-methyl-phenyl, 2-, 3-, 4-ethyl-phenyl, 2-, 3-, 4-n-propyl-phenyl, 2-, 3-, 4-i-propyl-phenyl, 2-, 3-, 4-n-butyl-phenyl, 2-, 3-, 4-tert.-butyl-phenyl, 1-, 2-methyl-naphthyl, 1-, 2-ethyl-naphthyl, 1-, 2-n-propyl-naphthyl, 1-, 2-i-propyl-naphthyl, 1-, 2-n-butyl-naphthyl, 1-, 2-tert.-butyl-phenyl.
C
6
-C
12
aryl-C
1
-C
12
alkyl stands for e.g. benzyl, 2-benzyl-2-propyl, &bgr;-phenyl-ethyl, &agr;,&agr;-dimethylbenzyl, &ohgr;-phenyl-butyl, &ohgr;,&ohgr;-dimethyl-&ohgr;-phenyl-butyl, &ohgr;-phenyl-dodecyl, &ohgr;-phenyl-octadecyl, &ohgr;-phenyl-eicosyl or &ohgr;-phenyl-docosyl, preferably C
7
-C
18
aralkyl such as benzyl, 2-benzyl-2-propyl, &bgr;-phenyl-ethyl, &agr;,&agr;-dimethylbenzyl, &ohgr;-phenyl-butyl, &ohgr;,&ohgr;-dimethyl-&ohgr;-phenyl-butyl, &ohgr;-phenyl-dodecyl or &ohgr;-phenyl-octadecyl, and particularly preferred C
7
-C
12
aralkyl such as benzyl, 2-benzyl-2-propyl, ,&bgr;phenyl-ethyl, &agr;&agr;-dimethylbenzyl, &ohgr;-phenyl-butyl, or &ohgr;,&ohgr;-dimethyl-&ohgr;-phenyl-butyl.
The inventive polymers and copolymers (hereinafter the term polymer comprises the term copolymer) usually have a molecular weight M
w
in the range of from 1,000 to 1,000,000 g/mol, preferably from 2,000 to 100,000 g/mol, most preferably from 2,000 to 50,000 g/mol.
A preferred embodiment of the present invention relates to a process for the preparation of a DPP polymer, comprising the following units:
which comprises reacting a

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