Triptycene polymers and copolymers

Details Triptycene polymers and copolymers Triptycene polymers and copolymers

2002-02-11

2003-08-12

Wilson, Donald R. (Department: 1713)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

From sulfur-containing reactant

C257S040000, C428S411100

Reexamination Certificate

active

06605693

ABSTRACT:

The invention relates to conjugated polymers and copolymers containing triptycene moieties.
There is a considerable industrial demand for large-area solid-state light sources for a number of applications, predominantly in the area of display elements, display-screen technology and illumination technology. The requirements made of these light sources cannot at present be met in an entirely satisfactory manner by any of the existing technologies.
As an alternative to conventional display and illumination elements, such as incandescent lamps, gas-discharge lamps and non-self-illuminating liquid-crystal display elements, electroluminescent (EL) materials and devices, such as light-emitting diodes (LEDs), have already been in use for some time.
Besides inorganic electroluminescent materials and devices, low-molecular-weight organic electroluminescent materials and devices have also been known for about 20 years (see, for example, U.S. Pat. No. 3,172,862). Until recently, however, such devices were greatly restricted in their practical usability.
WO 90/13148 and EP-A-0 443 861 describe electroluminescent devices which contain a film of a conjugate polymer as light-emitting layer (semiconductor layer). Such devices offer numerous advantages, such as the possibility of producing large-area, flexible displays simply and inexpensively. In contrast to liquid-crystal displays, electroluminescent displays are self-illuminating and therefore do not require any additional back-lighting source.
A typical device in accordance with WO 90/13148 consists of a light-emitting layer in the form of thin, dense polymer film (semiconductor layer) which comprises at least one conjugated polymer. A first contact layer is in contact with a first surface, a second contact layer is in contact with a further surface of the semiconductor layer. The polymer film of the semiconductor layer has a sufficiently low concentration of extrinsic charge carriers so that, on application of an electric field between the two contact layers, charge carriers are introduced into the semiconductor layer, the first contact layer being positive relative to the other, and the semiconductor layer emitting radiation. The polymers used in such devices are conjugated. The term conjugated polymer is taken to mean a polymer which has a delocalized electron system along the main chain. The delocalized electron system provides the polymer with semiconductor properties and enables it to transport positive and/or negative charge carriers with high mobility.
The polymeric material for the light-emitting layer using WO 90/13148 is poly(p-phenylenevinylene), and it is proposed to replace the phenyl group in a material of this type by a heterocyclic or a fused carbocyclic ring system. In addition, poly(p-phenylene), PPP, is also used as electroluminescent material (G. Grem et al., Synth. Met. 1992, 51, page 383).
Although good results have been achieved with these materials, the color purity, for example, is still unsatisfactory. Furthermore, it is virtually impossible to generate blue or white emission with the polymers disclosed hitherto.
Since, in addition, the development of electroluminescent materials, in particular based on polymers, can in no way be regarded as complete, the producers of illumination and display devices are interested in an extremely wide variety of electroluminescent materials for such devices.
One of the reasons for this is that only the interaction of the electroluminescent materials with the other components of the devices allows conclusions to be drawn on the quality of the electroluminescent material too.
German Patent Application 197 44 792.9, which has an earlier priority date and was published before the priority date of the present application, describes the use of triptycene derivatives as electroluminescent materials. This application relates to the monomeric triptycene derivatives, which, in order to be used as electroluminescent materials, are applied in the form of a film to a substrate by known methods, such as dipping, spin coating, vapor deposition or buffering out under reduced pressure.
The object of the present invention is to provide novel polymeric electroluminescent materials containing triptycene moieties which are suitable, on use in illumination or display devices, for improving the property profile of these devices.
The object has been achieved by a conjugated polymer containing
a) from 1 to 100 mol % of at least one recurring unit RU1 of the general formula (I)
—B—Tr—A—  (I)
 in which Tr is a triptycenylene radical of the general formula (II)
or of the general formula (III)
or of the general formula (IV)
where R
1
to R
16
=H, linear or branched C
1
-C
22
-alkyl or alkoxy, in which one or more non-adjacent CH
2
groups may be replaced by —O—, —S—, —CO—, —COO—, —O—CO—, an amino or amide group and in which one or more H atoms may be replaced by F atoms, or C
6
-C
20
-aryl or aryloxy, COOR, SO
3
R, CN, halogen or NO
2
,
where G, L and where appropriate G
1
and L
1
=CR
17
, N, P, As, where R
17
=H, C
1
-C
22
-alkyl or alkoxy, where one or more non-adjacent CH
2
groups may be replaced by —O—, —S—, —CO—, —COO—, —O—CO—, an amino or amide group and in which one or more H atoms may be replaced by F atoms, or C
6
-C
20
-aryl, halogen or CN,
A and B are a single bond, a vinylene radical which is optionally substituted by H, linear or branched C
1-C
22
-alkyl or alkoxy, in which one or more non-adjacent CH
2
groups may be replaced by —O—, —S—, —CO—, —COO—, —O—CO—, an amino or amide group and in which one or more H atoms may be replaced by F atoms, or C
6
-C
20
-aryl or aryloxy, C
3
-C
20
-heteroaryl, COOR, SO
3
R, CN, halogen, NO
2
, amino, alkylamino or dialkylamino, or are an ethynylene radical, an arylene radical of the general formula (V)
where R
18
to R
21
are as defined above for R
1
to R16,
a heteroarylene radical of the general formula (VI)
where X and Y=N or CR
22
, and Z=O, S, NR
23
, CR
24
R
25
, CR
26
=CR
27
or CR
28
=N—, in which R
22
to R
28
are as defined above for R
1
to R
16
, or a spirobifluorenylene radical of the general formula (VII)
where R
29
to R
32
are as defined above for R
1
to R
16
, and
b) from 0 to 99 mol % of at least one recurring unit RU2 of the general formula (VIII)
where R
33
to R
36
are as defined above for R
1
to R
16
, or of the general formula (IX)
where X, Y and Z are as defined above, and D is a single bond, a vinylene radical which is optionally substituted by H, linear or branched C
1
-C
22
-alkyl or alkoxy, in which one or more non-adjacent CH
2
groups may be replaced by —O—, —S—, —CO—, —COO—, —O—CO—, an amino or amide group and in which one or more H atoms may be replaced by F atoms, or C
6
-C
20
-aryl or aryloxy, C
3
-C
20
-heteroaryl, COOR, SO
3
R, CN, halogen, NO
2
, amino, alkylamino or dialkylamino, or is an ethynylene radical.
In a preferred embodiment of the invention, L, G and where appropriate L
1
and G
1
are a CH group.
A and B are a single bond, an optionally substituted vinylene radical, an ethynylene radical, an optionally substituted arylene radical, an optionally substituted heteroarylene radical or a spirobifluorenylene radical.
Preferred substituted vinylene radicals are methylvinylene, phenylvinylene and cyanovinylene.
Particular preference is given to an unsubstituted vinylene radical.
Preferred arylene radicals are 1,4-phenylene, 2,5-tolylene, 1,4-naphthylene, 1,9 antracylene, 2,7-phenantrylene and 2,7-dihydrophenantrylene.
Preferred heteroarylene radicals are 2,5-pyrazinylene, 3,6-pyridazinylene, 2,5-pyridinylene, 2,5-pyrimidinylene, 1,3,4-thiadiazol-2,5-ylene, 1,3-thiazol-2,4-ylene, 1,3-thiazol-2,5-ylene, 2,4-thiophenylene, 2,5-thiophenylene, 1,3-oxazol-2,4-ylene, 1,3-oxazol-2,5-ylene and 1,3,4-oxadiazol-2,5-ylene, 2,5-indenylene and 2,6-indenylene.
Methods for the synthesis of these monomers are based, for example, on the synthesis of 9,9′-spirobifluorene, for example from 2-bromobiphenyl and fluorenone via a Grignard synthesis, as descr

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