(Co)polymers based on vinyl units and use thereof in...

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Reexamination Certificate

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C428S523000, C428S917000, C313S504000, C313S506000, C252S301350, C526S256000, C526S259000, C526S260000, C526S268000, C526S280000, C526S284000

Reexamination Certificate

active

06403239

ABSTRACT:

Light-emitting components for electronics and photonics are today mainly developed using inorganic semiconductors, such as gallium arsenide. Punctual display elements may be produced using such substances. Devices of a large area are not possible.
In addition to semiconductor light emitting diodes, electroluminescent devices based on vapour-deposited low molecular weight organic compounds are also known (U.S. Pat. No. 4,539,507, U.S. Pat. No. 4,769,262, U.S. Pat. No. 5,077,142, EP-A 406 762). With these materials too, as a consequence of the production process, it is only possible to produce small LEDs. Furthermore, these electroluminescent devices have elevated production costs and only a very short service life.
Polymers such as poly(p-phenylenes) and poly(p-phenylene-vinylenes) are described as electroluminescent:
Adv. Mater
. 4 (1992) no. 1
; J. Chem. Soc., Chem. Commun
. 1992, pages 32-34
; Polymer
, 1990, volume 31, 1137
; Physical Review
B, volume 42, no. 18, 11670 or WO 90/13148.
In contrast to the fully conjugated polymers, non fully conjugated polycondensation products with luminescent structural units are described in electroluminescent devices (
Macromol. Chem. Phys
. 195, 2023-2037 (1994)).
The present invention provides polymers for the production of electroluminescent devices, which polymers are based on a well known basic structure, such as is polystyrene and polyacrylate, with covalently bonded luminophoric units in the side chains. Due to their simple production process and ready processability, such polymers are of great technical interest with regard to use as electroluminescent materials. Electroluminescent devices containing these (co)polymers are distinguished by elevated light intensities and a broad range of colour hues. The advantages of the (co)polymers according to the invention are, for example, that
1. light intensity may purposefully be modified by varying the concentration of luminophore,
2. colour hues may be adjusted by combining different monomers containing luminophores,
3. the morphology and electrical properties of the polymer layers may be optimised by the incorporation of suitable side chain units.
The present invention relates to (co)polymers which contain at least one repeat chain unit of the general formula (1) or (2) and optionally contain repeat units of the general formula (3)
in which
R
1
, R
2
and R
3
mutually independently mean hydrogen or C
1
-C
6
alkyl,
M denotes CN or C
1
-C
30
alkoxycarbonyl, C
1
-C
30
(di)alkyl-aminocarbonyl, C
1
-C
30
alkylcarbonyl, which may each be substituted by hydroxy or C
1
-C
6
alkoxycarbonyl, and furthermore denotes phenyl, naphthyl, anthracenyl, pyridyl or carbazolyl, which may each be substituted by residues from the group halogen, hydroxy, silyl, C
1
-C
30
alkyl, C
6
-C
18
aryl, C
1
-C
30
alkoxy, C
1
-C
30
alkoxycarbonyl, C
1
-C
30
acyloxy and C
1
-C
30
alkylcarbonyl,
L
1
and L
2
mean a photoluminescent residue,
wherein the proportion of structural units of the formula (3) is 0 to 99.5, preferably 40 to 99.5 mol. % and the proportion of structural units (1) and/or (2) is in each case 0.5 to 100, preferably 0.5 to 60 mol. % and the molar proportions add up to 100%.
In the above-stated formulae, R
1
, R
2
and R
3
mutually independently preferably mean hydrogen, methyl or ethyl.
M preferably denotes CN or C
1
-C
15
alkoxycarbonyl, C
1
-C
15
(di)alkylamnino-carbonyl, C
1
-C
15
alkylcarbonyl, which may each be substituted by hydroxy or methoxycarbonyl, ethoxycarbonyl, n- or iso-propoxycarbonyl, and furthermore denotes phenyl, naphthyl, anthracenyl, pyridyl or carbazolyl, which may each be substituted by residues from the group chlorine, bromine, hydroxy, silyl, C
1
-C
6
alkyl, C
1
-C
6
alkoxy, C
1
-C
6
alkoxycarbonyl, C
1
-C
6
acyloxy and C
1
-C
6
alkyl-carbonyl, phenyl optionally substituted by methyl, ethyl, n- or iso-propyl.
L1 and L2 mutually independently denote a photoluminescent residue which is based on the skeleton of a fluorescent dye which is selected from the group of coumarins of the formula (4)
pyrenes of the formula (5)
1,8-naphthalimides of the formula (6)
1,8-naphthaloylene-1′,2′-benzimidazoles of the formulae (7a) and (7b)
phenothiazines or phenoxazines of the formula (8)
benzopyrones of the formula (9)
carbazoles, fluorenes, dibenzothiophenes and -furans of the formula (10)
oxazoles, 1,3,4-oxadiazoles of the formula (11)
benzoquinolines of the formula (12)
9,10-bis-(phenylethynyl)anthracenes of the formula (13)
fluorones of the formula (14)
9,10-diphenylanthracene of the formula (15)
2-styrylbenzazole of the formula (16)
wherein
R
4
denotes hydrogen, C
1
-C
30
alkyl, C
6
-C
18
all, C
7
-C
24
aralkyl or C
1
-C
30
alkoxy or
 wherein
R
43
and R
44
mutually independently denote hydrogen, C
1
-C
30
alkyl C
6
-C
18
aryl, C
7
-C
24
aralkyl, which may each be substituted by hydroxy, amino, carboxy or C
1
-C
4
alkoxycarbonyl, or
R
43
and R
44
, together with the nitrogen atom to which they are attached, may mean a morpholine, piperidine, pyrrolidine or piperazine ring, which may bear one or two substituents from the group methyl, ethyl and phenyl,
R
5
denotes hydrogen, cyano, C
1
-C
30
alkyl, C
6
-C
18
aryl, C
7
-C
24
aralkyl, C
1
-C
30
alkoxy, C
2
-C
12
acyl, C
1
-C
12
alkoxycarbonyl, C
1
-C
12
(di)alkylamino-carbonyl,
R
6
denotes hydrogen, cyano, C
1
-C
30
alkyl, C
6
-C
18
aryl, C
7
-C
24
aralkyl, C
1
-C
30
alkoxy or
wherein Z denotes a group OR
45
or
R
45
, R
46
and R
47
mutually independently denote C
1
-C
30
alkyl, C
6
-C
18
aryl or C
7
-C
24
aralkyl, wherein the aromatic rings may additionally be further substituted by halogen, C
1
-C
6
alkyl, C
1
-C
6
alkoxy,
R
7
, R
8
and R
9
mutually independently mean hydrogen, C
1
-C
30
alkyl, C
6
-C
18
aryl, C
7
-C
24
aralkyl, C
1
-C
30
alkoxy, cyano, C
2
-C
12
acyl, C
1
-C
12
alkoxycarbonyl, C
1
-C
12
(di)alkyl-aminocarbonyl or an amino group with one or two C
1
-C
6
alkyl groups,
R
10
means hydrogen, cyano, C
1
-C
30
alkyl, C
6
-C
18
aryl, C
7
-C
24
aralkyl, C
1
-C
30
alkoxy, amino, C
2
-C
12
acyl, C
1
-C
12
alkoxycarbonyl, C
1
-C
12
(di)alkylamino-carbonyl,
R
11
denotes hydrogen, halogen, nitro, C
1
-C
4
alkoxycarbonyl, C
1
-C
4
acyl, C
8
-C
24
aralkenyl, unsubstituted amino, or amino identically or differently mono- or disubstituted by C
1
-C
30
alkyl, C
1
-C
18
aryl or C
7
-C
24
aralkyl,
R
11
furthermore denotes morpholinyl, piperidinyl, pyrrolidinyl or piperazinyl, which may bear one or two substituents selected from methyl, ethyl and/or phenyl,
R
12
denotes hydrogen, C
1
-C
30
alkyl, C
6
-C
18
aryl, C
7
-C
24
aralkyl or C
1
-C
30
alkoxy,
R
13
denotes hydrogen, C
1
-C
30
alkyl, C
6
-C
18
aryl, C
7
-C
24
aralkyl, C
1
-C
30
alkoxy or
 wherein
R
49
and R
50
mutually independently denote C
1
-C
30
alkyl, C
6
-C
18
aryl, C
7
-C
24
aralkyl or
R
49
and R
50
, together with the nitrogen atom to which they are attached, moreover denote a morpholinyl, piperidinyl, pyrrolidinyl or piperazinyl, which may bear one or two identical or different substituents selected from methyl, ethyl and phenyl,
R
14
and R
15
mutually independently mean hydrogen, cyano, halogen, nitro, C
1
-C
30
alkyl, C
1
-C
30
alkoxy, C
6
-C
18
aryl or C
7
-C
24
aralkyl, C
1
-C
12
alkoxycarbonyl, C
2
-C
12
acyl, C
1
-C
12
(di)alkylaminocarbonyl, C
1
-C
6
(di)alkyl-amino,
R
17
and R
23
mutually independently mean hydrogen, C
1
-C
30
alkyl, C
6
-C
18
aryl or C
7
-C
24
aralkyl and
R
16
, R
18
to R
22
and R
24
to R40 mutually independently mean hydrogen, cyano, C
1
-C
30
alkyl, C
6
-C
18
aryl, C
7
-C
24
aralkyl, C
1
-C
30
alkoxy, an amino group with one or two C
1
-C
6
alkyl groups, unsubstituted amino, C
2
-C
12
acyl, C
1
-C
12
alkoxycarbonyl or C
1
-C
12
(di)alkylaminocarbonyl, wherein the aliphatic carbon chains, such as, for example, alkyl, alkoxy, alkylamino, aralkyl, in the residues R
4
to R
13
, R
16
to R
40
may be interrupted by one or more, preferably one or two heteroatoms selected from oxygen, nitrogen and

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