IP Library Granted Patent US 7,696,284
Granted Patent B2
US 7,696,284 · App. 10/572,117 · Granted Apr 13, 2010

White-emitting copolymers, representation and use thereof

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Quick Facts
Patent No.
US 7,696,284
App. No.
10/572,117
Granted
Apr 13, 2010
Kind
B2
Abstract

The present invention relates to white-emitting copolymers which are obtained by a combination of blue-, green- and red-emitting repeating units. The copolymers of the invention display better film formation and an improved efficiency when used in polymeric organic light-emitting diodes compared to materials according to the prior art.

Claims (26)

1. The white-emitting copolymer comprising at least three different repeating units, characterized in that the first repeating unit, unit B, is present in a proportion of at least 10 mol % and displays blue emission, the second repeating unit, unit G, is present in the polymer in a proportion of from 0.001 to 3 mol % and displays green emission and the third repeating unit, unit R, is present in a proportion of from 0.0005 to 1 mol % and displays red emission with the proviso that this unit B is not a carbazole when the polymer is a nonconjugated phosphorescent polymer; and with the exception of a polymer comprising the repeating units (a), (b) and (c),

where the content of monomer (b) is in the range from 2.32 to 2.34 mol % and the content of monomer (c) is in the range from 0.174 to 0.176 mol %.

2. The copolymer as claimed in claim 1 , characterized in that the proportion of red repeating units R is less than the proportion of green repeating units G.

3. The copolymer as claimed in claim 2 , characterized in that the ratio of red repeating units to green repeating units (units R:G) is from 1:50 to 1:1.1.

4. The copolymer as claimed in claim 1 , characterized in that the green-emitting repeating unit G is selected from the group consisting of electron-rich bis(styryl)arylenes and corresponding extended structures, beuzothiadiazoles, quinoxalines, phenothiazines, dihydrophenazines, bis(thienyl)arylenes, oligo(thienylenes), phenazines and corresponding derivatives containing oxygen instead of sulfur.

5. The copolymer as claimed in claim 4 , characterized in that the green-emitting repeating units G are selected from the group consisting of the units of the formulae (I) to (XII), which may be substituted or unsubstituted:

where the symbols and indices used have the following meanings:

Y is identical or different on each occurrence and is in each case S or O;

Ar is identical or different on each occurrence and is in each case an aromatic or heteroaromatic ring system which has from 3 to 30 carbon atoms and may be unsubstituted or substituted by fluorine or by one or more radicals R, OR or NR 2 , with the proviso that at least one unit Ar in the formulae (IX) and (X) is an electron-rich aromatic unit or is substituted by electron-rich substituents;

R is identical or different on each occurrence and is in each case H, a linear, branched or cyclic alkyl chain which has from 1 to 22 carbon atoms and in which one or more nonadjacent carbon atoms may also be replaced by O, S, —CO—O— or —O—CO—O—, where one or more H atoms may also be replaced by fluorine, or a substituted or unsubstituted aryl group which has from 5 to 40 carbon atoms and in which one or more carbon atoms may also be replaced by O, S or N;

p is identical or different on each occurrence and is in each case 1, 2, 3, 4 or 5;

and the broken-line bonds indicate the linkage in the polymer.

6. The copolymer as claimed in claim 1 , characterized in that units which display electrophosphorescence instead of electrofluorescence are used as blue-, green- and/or red-emitting repeating units B, G and/or R.

7. The copolymer as claimed in claim 6 , characterized in that these units comprise elements having an atomic number of more than 36.

8. The copolymer as claimed in claim 7 , characterized in that these elements are selected from among elements of groups 8 to 10 of the periodic table.

9. The copolymer as claimed in claim 1 , characterized in that more than one blue-emitting repeating unit B is used and/or that more than one green-emitting repeating unit G is used, with the total proportion of green-emitting repeating units G being not more than 3 mol %, and/or that more than one red-emitting repeating unit R is used, with the total proportion of red-emitting repeating units R being not more than 1 mol %.

10. The copolymer as claimed in claim 1 , characterized in that the proportion of blue-emitting repeating units B is at least 20 mol %, the proportion of green-emitting repeating units G is not more than 2 mol % and the proportion of red-emitting repeating units R is from 0.0005 to 0.5 mol % and the ratio of red-emitting repeating units to green-emitting repeating units (units R:G) is in the range from 1:50 to 1:1.1.

11. A blend comprising at least one copolymer as claimed in claim 1 and at least one further polymeric, oligomeric, dendritic or low molecular weight compound.

12. A solution or formulation comprising one or more copolymers or blends as claimed in claim 1 in one or more solvents.

13. A polymeric light-emitting diode (PLED) having one or more active layers of which at least one comprises a copolymer or blend as claimed in claim 1 .

14. A white-emitting display comprising a PLED as claimed in claim 13 .

15. A color, multicolor or full-color display in which the color is produced by use of a color filter on a white-emitting PLED as claimed in claim 13 .

16. A lighting element comprising a PLED as claimed in claim 13 .

17. A liquid crystal display (LCD) comprising a white-emitting PLED as claimed in claim 13 as backlight.

18. An organic solar cell, organic laser diode, organic integrated circuit, organic field effect transistor or organic thin film transistor comprising at least one polymer or blend as claimed in claim 1 .

19. The copolymer as claimed in claim 7 , characterized in that these elements are Ru, Os, Rh, It, Pd or Pt.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 29, 2007
From: MERCK OLED MATERIALS GMBH
To: MERCK PATENT GMBH
Reel/Frame 018821/0477 →
CHANGE OF NAME Recorded Jul 1, 2006
From: COVION ORGANIC SEMICONDUCTORS GMBH
To: MERCK OLED MATERIALS GMBH
Reel/Frame 018097/0118 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 12, 2006
From: FALCOU, AURELIE; BUSING, ARNE; HUEN, SUSANNE; STEIGER, JURGEN; GERHARD, ANJA; SCHULTE, NIELS; BECKER, HEINRICH
To: COVION ORGANIC SEMICONDUCTORS GMBH
Reel/Frame 017778/0366 →