Electroluminescent element

• US 5,281,489 A
• Filed: 09/16/1991
• Issued: 01/25/1994
• Est. Priority Date: 03/16/1990
• Status: Expired due to Term

• Current Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
• Original Assignee: Asahi Kasei Kabishiki Kaisha
• Inventors: Endo, Hiroshi, Mori, Yoshihiko
• Primary Examiner(s): Robinson, Ellis P.
• Assistant Examiner(s): Nold, Charles R.
• Application Number:
  US07/760,190
• Time in Patent Office: 862 Days
• Field of Search: 428/690, 428/691, 428/917, 313/503, 313/504, 313/506, 313/507, 313/498
• US Class Current: 428/690
• 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: H10K 2101/90 Multiple hosts in the emissive layer
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/14 Carrier transporting layers
• CPC Class Codes: H10K 71/841 Applying alternating current [AC] during manufacturing or treatment
• CPC Class Codes: H10K 85/111 comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
• CPC Class Codes: H10K 85/141 comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/631 Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
• CPC Class Codes: H10K 85/649 Aromatic compounds comprising a hetero atom
• CPC Class Codes: H10K 85/652 Cyanine dyes
• CPC Class Codes: H10K 85/6565 Oxadiazole compounds
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

Disclosed is an electroluminescent element comprising an anode, a cathode and, disposed therebetween, an organic luminescent layer comprising a mixture of a fluorescent luminescent agent, at least one hole moving and donating agent capable of moving holes and donating the same to the luminescent agent and at least one electron moving and donating agent capable of moving electrons and donating the same to the luminescent agent. In the element, the components of the luminescent layer have specific oxidation potential and reduction potential relationships. The element emits light in response to electrical signals. The element exhibits high luminescence efficiency and brightness even at low voltages, and it can efficiently be produced at low cost.

Claims

1. An electroluminescent element comprising:

an anode for injecting holes, a cathode for injecting electrons and, disposed therebetween, an organic luminescent layer, at least one of said anode and cathode being transparent,

said organic luminescent layer comprising a three component mixture of at least one fluorescent luminescent agent, at least one hole moving and donating agent capable of moving the holes injected from said anode and donating the holes to said luminescent agent, and at least one electron moving and donating agent capable of moving the electrons injected from said cathode and donating the electrons to said luminescent agent,

said luminescent agent having a first oxidation potential which is equal to or less noble relative to that exhibited by said hole moving and donating agent,

said luminescent agent having a first reduction potential which is equal to or noble relative to that exhibited by said electron moving and donating agent,

said first oxidation potential of each of said three component agents and said first reduction potential of each of said three component agents being measured by cyclic voltammetry with respect to a solution of said agent in a solvent for said agent.

2. The electroluminescent element according to claim 1, wherein said hole moving and donating agent has a first reduction potential less noble relative to that exhibited by said electron moving and donating agent, and said electron moving and donating agent has a first oxidation potential noble relative to that exhibited by said hole moving and donating agent.

3. The electroluminescent element according to claim 1, wherein said hole moving and donating agent is comprised of at least one compound having at least two benzene nuclei and at least one nitrogen atom.

4. The electroluminescent element according to claim 3, wherein said compound is selected from the group consisting of a tertiary amine compound, a hydrazone compound, a pyrazoline compound, an enamine compound, a styryl compound, a stilbene compound, a triphenylmethane compound having an amino substituent and an oxadiazole compound having an amino substituent.

5. The electroluminescent element according to claim 3, wherein said compound is a carbazole compound.

6. The electroluminescent element according to claim 5, wherein said carbazole compound is selected from the group consisting of N-isopropylcarbazole, N-phenylcarbazole and N-ethylcarbazole.

7. The electroluminescent element according to claim 1, wherein said hole moving and donating agent is comprised of at least one polymer having a hole mobility of at least 1×

10^-10 cm² /V·

sec at a field strength of 1×

10⁵ V/cm.

8. The electroluminescent element according to claim 7, wherein said polymer is a homopolymer or a copolymer of an ethylenically unsaturated monomer.

9. The electroluminescent element according to claim 8, wherein said polymer is a poly(N-vinylcarbazole) homopolymer.

10. The electroluminescent element according to claim 1, wherein said electron moving and donating agent is comprised of at least one polynuclear compound having at least 3 condensed rings.

11. The electroluminescent element according to claim 10, wherein said polynuclear compound is selected from the group consisting of an anthracene compound, a phenanthrene compound, a pyrene compound, a perylene compound, a chrysene compound, a triphenylene compound, a fluoranthene compound and a periflanthene compound.

12. The electroluminescent element according to claim 1, wherein said electron moving and donating agent is comprised of at least one heterocyclic compound.

13. The electroluminescent element according to claim 12, wherein said heterocyclic compound is an azole compound or a diazole compound.

14. The electroluminescent element according to claim 13, wherein said azole compound and diazole compound are an oxazole compound and an oxadiazole compound, respectively.

15. The electroluminescent element according to claim 1, wherein said electron moving and donating agent is comprised of at least one vinylene compound.

16. The electroluminescent element according to claim 1, wherein said electron moving and donating agent is comprised of at least one polymer.

17. The electroluminescent element according to claim 16, wherein said polymer is a homopolymer or a copolymer of an ethylenically unsaturated polynuclear compound monomer having at least 3 condensed rings.

18. The electroluminescent element according to claim 16, wherein said polymer has a main chain or a side chain having a heterocyclic compound group.

19. The electroluminescent element according to claim 18, wherein said polymer has a main chain or a side chain having an oxadiazole unit.

20. The electroluminescent element according to claim 1, wherein said luminescent agent is comprised of at least one condensed polynuclear aromatic compound having at least 3 condensed rings.

21. The electroluminescent element according to claim 1, wherein said luminescent agent is comprised of at least one aromatic compound having at least 3 benzene nuclei.

22. The electroluminescent element according to claim 1, wherein said luminescent agent is comprised of at least one dye.

23. The electroluminescent element according to claim 22, wherein said dye is selected from the group consisting of a coumarin fluorescent dye, a dicyanopyran fluorescent dye, a thiopyran fluorescent dye, a polymethine fluorescent dye, a cyanine fluorescent dye, an oxabenzanthracene fluorescent dye, a xanthene fluorescent dye, a Rhodamine fluorescent dye, a fluorescein fluorescent dye, an acridine fluorescent dye, a bis(styryl)benzene fluorescent dye, a pyrene fluorescent dye, an oxazine fluorescent dye, a phenylene oxide fluorescent dye, a pyrylium fluorescent dye, a thiapyrylium fluorescent dye, a carbostyryl fluorescent dye and a perylene fluorescent dye.

24. The electroluminescent element according to claim 1, wherein said organic luminescent layer is a layer prepared by dissolving or dispersing said luminescent agent, said hole moving and donating agent and said electron moving and donating agent in a solvent to obtain a solution or a dispersion, and applying the solution or the dispersion to said anode or said cathode to form a coating thereon, and drying the coating to form the organic luminescent layer.

25. The electroluminescent element according to claim 24, wherein said coating is subjected to leveling under a solvent vapor during the drying.

26. The luminescent element according to claim 24, wherein said organic luminescent layer contains at least one binder polymer.

27. The luminescent element according to claim 26, wherein said binder polymer is a curable resin.

28. The luminescent element according to claim 1 or 24, wherein the weight ratio of said hole moving and donating agent to said electron moving and donating agent is in the range of from 5:

95 to 95;

5.

29. The luminescent element according to claim 1 or 24, wherein said luminescent agent is comprised in said organic luminescent layer in an amount of from 0.01 to 20 parts by weight, relative to 100 parts by weight of the total of the hole moving and donating agent and the electron moving and donating agent.

30. The luminescent element according to claim 1 or 24, wherein said organic luminescent layer has a thickness of 1 μ

m or less.

31. The luminescent element according to claim 1 or 24, which further comprises at least one member selected from the group consisting of a hole injecting and transporting layer disposed between said anode and said organic luminescent layer and a hole inhibiting layer disposed between said organic luminescent layer and said cathode,

said hole injecting and transporting layer facilitating the injection of holes from said anode and transporting the injected holes to said organic luminescent layer,

said hole inhibiting layer inhibiting passage of the holes into said cathode to hold the holes within said organic luminescent layer, thereby allowing the holes to effectively contribute to luminescence.

32. The electroluminescent element according to claim 1 or 24, wherein said element is driven by alternate current.

33. The electroluminescent element according to claim 1 or 24, wherein said element exhibits a statistical brightness dispersion of not greater than 5% relative to an average brightness of from 122.8 to 182.9 cd/m².

34. The electroluminescent element according to claim 1 or 24, wherein said hole moving and donating agent has a first oxidation potential which is less noble as compared to +2.0 V.

35. The electroluminescent element according to claim 1 or 24, wherein said electron moving and donating agent has a first reduction potential which is noble as compared to -2.50 V.