Fluorene-based alternating copolymers for electroluminescence element and electroluminescence element using such copolymers as light emitting materials

• US 5,807,974 A
• Filed: 11/26/1996
• Issued: 09/15/1998
• Est. Priority Date: 05/16/1996
• Status: Expired due to Fees

• Current Assignee: Korea Advanced Institute of Science and Technology
• Original Assignee: Korea Advanced Institute of Science and Technology
• Inventors: Kim, Young Chul, Cho, Hyun Nam, Lee, Jun Young, Kim, Jai Kyeong, Kim, Dong Young, Kim, Chung Yup
• Primary Examiner(s): BOYKIN, TERRESSA M
• Application Number:
  US08/756,036
• Time in Patent Office: 658 Days
• Field of Search: 528/176, 528/271, 528/330, 528/366, 528/392, 428/457, 428/690, 428/917, 313/507
• US Class Current: 528/366
• CPC Class Codes: C08G 61/00 Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule C08G2/00 - C08G16/00 take precedence
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: Y10S 428/917 Electroluminescent
• CPC Class Codes: Y10T 428/31678 Of metal

Abstract

The present invention relates to a fluorene-based alternating copolymer to be used as light emitting materials of electroluminescent elements having the following formula (I), and further relates to electroluminescent elements having an anode/luminescent layer/cathode structure, in which the fluorene-based alternating copolymer used as light emitting materials of the luminescent layer, or having a transporting and/or reflection layer added thereto, if necessary, is ##STR1## where R, R'"'"', X, Ar and n are defined in the text.

Claims

1. A fluorene-based alternating copolymer used for luminescent materials of electroluminescent elements, indicated by the following formula (I):

##STR33## where R and R'"'"' which are identical or different, are selected from the group consisting of hydrogen, aliphatic or alicyclic alkyl or alkoxy groups containing 1 to 22 carbon atoms, or aryl or aryloxy group containing 6 to 18 carbon atoms;

X represents hydrogen or a cyano group;

Ar represents compounds substituted from aliphatic or alicyclic alkyl groups containing 1 to 22 carbons, phenyl groups in ortho, meta or para position, or aliphatic or alicyclic alkyl or alkoxy groups containing 1 to 22 carbons, diphenyl, diphenylether, diphenylsulfide and diphenylamine compounds, compounds having two or more phenyl groups, such as pyridine, furan, compounds having hetero atoms, diphenylmethane or diphenylsilane compounds, and bisformylphenoxyalkane or alkoxy compounds; and

n represents an integer greater than or equal to 1.

2. An electroluminescent element consisting of anode/luminescent layer/cathode or anode/hole transporting layer/luminescent layer/electron transporting layer/cathode, characterized in that a light emitting material of the luminescent layer is a fluorene-based alternating copolymer of formula (I) according to claim 1.

3. The electroluminescent element according to claim 2, characterized in that the light emitting material of the luminescent layer is a material in which the fluorene-based alternating copolymer having the formula (I) and macromolecule for general use are blended together.

4. The electroluminescent element according to claim 3, characterized in that the macromolecule for general use are selected from the group consisting of polyvinylcarbazole, polymethylmethacrylate, polystyrene and epoxy.

5. The electroluminescent element according to claim 3, characterized in that the fluorene-based alternating copolymer having the formula (I) is blended in the amount of 0.1 to 99.9 weight % based on the amount of the macromolecule for general use.

6. The electroluminescent element according to claim 2, characterized in that the luminescent layer is in the form of a film having thickness of 5 nanometers to 5 microns and a fluorene-based alternating copolymer concentration of more than 0.001% by weight.

7. The electroluminescent element according to claim 6, in which the film thickness of 50 nanometers to 1 micron and the concentration is 0.1-50% by weight.

8. A fluorene-based alternating copolymer according to claim 1 in which R and R'"'"' are individually selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, isooctyl, nonyl, decyl, dodecyl, hexadecyl, octadecyl, docodecyl, cyclopropyl, cyclopentyl, cyclohexyl, methoxy, ethoxy, butoxy, hexyloxy, methoxyethoxyethyl, methoxyethoxyethoxyethyl, phenyl, phenoxy, tolyl, benzyl, naphthyl and anthracene groups;

and Ar represent alkyl, alkoxy, dialkyl or dialkoxyphenyl, fluorene, terphenyl, naphthalene, anthracene, pyridine, furan, thiophene, alkylthiophene, dithiophene, pyrrole, dipyrrole, dipyrrolementane, dibenzofuran, dibenzothiophene, diphenyloxadiazole, dipheylthiadiazole and carbazole.

9. The fluorene-based alternating copolymer according to claim 1 characterized in that R and R'"'"' are individually selected from a group consisting of hydrogen and alkyl, and the copolymer has a polymerization degree of 1 to 2,000.

10. The fluorene-based alternating copolymer according to claim 9 characterized in that Ar comprises a divalent form of a radical selected from the group of phenyl, pyrrole, thiophene, furan, pyridine and carbazole, and the copolymer has a degree of polymerization of 3 to 1,000.

11. The fluorene-based alternating copolymer according to claim 10 characterized in that R is hexyl.

12. The fluorene-based alternating copolymer according to claim 11 in which R'"'"' is hexyl.

13. The fluorene-based alternating copolymer according to claim 11 in which X is cyano.

14. The fluorene-based alternating copolymer according to claim 12 in which X is hydrogen.

15. The fluorene-based alternating copolymer according to claim 11 in which X is hydrogen.

16. An electroluminescent element consisting of anode/luminescent layer/cathode or anode/hole transporting layer/luminescent layer/electron transporting layer/cathode, characterized in that a light emitting material of the luminescent layer is a fluorene-based alternating copolymer of formula (I) according to claim 9.

17. The electroluminescent element according to claim 16, characterized in that the light emitting material of the luminescent layer is a blend of the fluorene-based alternating copolymer having the formula (I) and macromolecule for general use.

18. An electroluminescent element consisting of anode/luminescent layer/cathode or anode/hole transporting layer/luminescent layer/electron transporting layer/cathode, characterized in that a light emitting material of the luminescent layer is a fluorene-based alternating copolymer of formula (I) according to claim 10.

19. An electroluminescent element consisting of anode/luminescent layer/cathode or anode/hole transporting layer/luminescent layer/electron transporting layer/cathode, characterized in that a light emitting material of the luminescent layer is a fluorene-based alternating copolymer of formula (I) according to claim 11.

20. An electroluminescent element consisting of anode/luminescent layer/cathode or anode/hole transporting layer/luminescent layer/electron transporting layer/cathode, characterized in that a light emitting materials of the luminescent layer if a fluorene-based alternating copolymer of formula (I) according to claim 14.