Compositions – Organic luminescent material containing compositions
Patent
1998-05-29
2000-10-17
Yoon, Tae
Compositions
Organic luminescent material containing compositions
25230121, 25230135, 428917, C09K 1106, C09K 1100
Patent
active
061326410
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to unsubstituted and substituted poly(9,9'-spirobisfluorenes); a process for their preparation; a composition comprising a support material and a layer of an unsubstituted or substituted poly(9,9'-spirobisfluorene), which may, if desired, further comprise a luminophore; a composition comprising an unsubstituted or substituted poly(9,9'-spirobisfluorene) which comprises a luminophore; and the use of the compositions or the poly(9,9'-spirobisfluorenes) as fluorophores, for example in light-emitting diodes or electrodes in display applications, and also 2,2'-dihalo-7,7'-disubstituted 9,9'-bisfluorenes.
In recent times, materials which emit fluorescent radiation have attracted greatly increased interest for display elements or photodiodes. In Adv. Mater. 1994, 6, No. 3, pages 190 to 198, J. M. Tour describes polyphenylenes which are known to emit blue fluorescent light. The good mechanical and thermal properties of the polyphenylenes are known. The insolubility in organic solvents and the associated unsatisfactory processibility and also the instability of doped polyphenylenes greatly impairs commercial utilization. There is a great need for blue-fluorescing and processible materials based on aromatic hydrocarbons, which materials have excellent thermal and mechanical properties (for example thermal stabilities above 200.degree. C.); the polymers should be able to be prepared easily and, in particular, the targeted preparation of defined polymers should be possible. Furthermore, it is desirable for the polymers to be suitable as matrix for the incorporation of small amounts of different fluorophores in order to obtain fluorescent emissions over the entire visible spectrum.
It has now surprisingly been found that 9,9'-bisfluorenes can be polymerized to give blue-fluorescing polymers which are soluble in many solvents and are therefore also readily processible, for example by means of customary coating processes. The polymers have excellent thermal and mechanical stabilities and are excellent matrix systems for the incorporation of molecular fluorophores which can be used in fluorescent displays and in electroluminescent displays.
The invention provides, firstly, soluble poly(bis-9,9'-fluorenes) comprising identical or different structural repeating units of the formula I, ##STR2## where the two R.sub.1 s are, independently of one another, H, C.sub.1 -C.sub.18 alkyl, C.sub.6 -C.sub.14 aryl, C.sub.7 -C.sub.15 aralkyl, C.sub.1 -C.sub.18 alkoxy, R.sub.2 --(O--C.sub.n H.sub.2n).sub.m --O--, C.sub.1 -C.sub.18 alkylthio, C.sub.1 -C.sub.18 dialkylamino, --C(O)OH, --C(O)O-C.sub.1 -C.sub.18 alkyl, --C(O)--N(C.sub.1 -C.sub.18 alkyl).sub.2, --SO.sub.3 H, --SO.sub.3 -C.sub.1-C.sub.18 alkyl, --SO.sub.2 --N(C.sub.1 -C.sub.18 alkyl).sub.2, C.sub.1 -C.sub.17 alkly-C(O)--O-- or C.sub.1 -C.sub.17 alkyl-C(O)--, R.sub.2 is H or C.sub.1 -C.sub.12 alkyl, n is from 2 to 6 and m is from 1 to 12.
The alkyl groups in alkyl, alkoxy, alkylthio, diaminoalkyl, carboxylic ester or sulfonic ester, carboxamide or sulfonamide, alkyl-CO.sub.2 -- and alkyl-C(O)-- radicals R.sub.1 can be linear or branched and preferably contain from 1 to 12, particularly preferably from 1 to 8, C atoms. Some examples of alkyl are methyl, ethyl, n- and i-propyl, n-, i- and t-butyl, and the isomers of pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl and octadecyl.
Aryl radicals R.sub.1 preferably contain from 6 to 10 C atoms. Some examples are naphthyl, biphenylyl and, particularly preferably, phenyl.
Aralkyl radicals R.sub.1 preferably contain from 7 to 12 C atoms and the alkylene group in the aralkyl radical preferably contains 1 or 2 C atoms. A preferred example is benzyl and also phenylethyl.
Halogen atoms R.sub.1 are preferably F, Cl or Br.
Alkyl radicals R.sub.2 preferably contain from 1 to 8 and particularly preferably from 1 to 4 C atoms. They can be linear or branched. Some examples are methyl, ethyl, n-propyl and n-butyl.
In the radical R.sub.2 --(O--C.sub.n H.sub.2n).sub.m --O--, n is prefer
REFERENCES:
patent: 5026894 (1991-06-01), Tour et al.
patent: 5621131 (1997-04-01), Kreuder et al.
Adv. Mater., vol. 6, No. 3, (1994), pp. 190-198.
Tetrahedron Lett., vol. 32, No. 39, (1991), pp. 5309-5312.
Chem. Abstr. 116:41262.
ISR. J. Chem., vol. 32, No. 1, (1992), pp. 69-77.
Chem. Abstr., 118:233206.
Macromolecules, vol. 25, No. 4, (1992), pp. 1214-1223.
Chem. Abstr. 113:192072.
Polymer Prepr. (Am. Chem. Soc., Div. Polym. Chem.), vol. 31, No. 1, (1990), pp. 408-409.
Rietz Ralf-Roman
Wernet Wolfgang
Crichton David R.
Kovaleski Michele A.
Vantico Inc.
Yoon Tae
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