Condensed eight-ring aromatic compound, and organic EL element and organic EL display using the same

• US 6,805,977 B2
• Filed: 03/25/2002
• Issued: 10/19/2004
• Est. Priority Date: 08/29/2001
• Status: Expired due to Term

• Current Assignee: UDC Ireland Limited
• Original Assignee: Fujitsu Limited
• Inventors: Sato, Hiroyuki, Matsuura, Azuma, Sotoyama, Wataru, Narusawa, Toshiaki
• Primary Examiner(s): Yamnitzky, Marie
• Assistant Examiner(s): THOMPSON, CAMIE S
• Application Number:
  US10/104,013
• Publication Number:
  US 20030082404A1
• Time in Patent Office: 939 Days
• Field of Search: 428/690, 428/917, 313/506, 313/504, 252/301.16, 564/426
• US Class Current: 428/690
• CPC Class Codes: C07C 15/20 Polycyclic condensed hydrocarbons
• CPC Class Codes: C07C 211/61 with at least one of the condensed ring systems formed by three or more rings
• CPC Class Codes: C07C 2603/54 containing more than five condensed rings
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/60 Organic compounds having low molecular weight H10K85/10 - H10K85/50 take precedence
• CPC Class Codes: H10K 85/624 containing six or more rings
• 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 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

The object of the present invention is to provide an organic EL element which utilizes a novel condensed eight-ring aromatic compound, and has high color purity of red light and excellent light-emitting efficiency, light-emitting luminance and the like. The organic EL element of the present invention has, in between a positive electrode and a negative electrode, an organic thin-film layer including a light-emitting layer. The organic thin-film layer contains the condensed eight-ring aromatic compound which has a number of regions where substituents can be introduced is any of 14, 16 and 18, and the condensed eight-ring aromatic compound has a point-symmetrical skeleton.

Claims

1. A condensed eight-ring aromatic compound, wherein the condensed eight-ring aromatic compound has a point-symmetrical skeleton (excluding such cases in which the regions where substituents can be introduced are all hydrogen atoms),

wherein the condensed eight-ring aromatic compound is represented by any of following structural formulas (1) through (3):

where R¹ through R¹⁸ may be the same or may be different from each other, and represent hydrogen atoms or substituents (excluding cases in which all are hydrogen atoms);

where R¹ through R¹⁶ may be the same or may be different from each other, and represent hydrogen atoms or substituents (excluding cases in which all are hydrogen atoms);

where R¹ through R¹⁴ may be the same or may be different from each other, and represent hydrogen atoms or substituents (excluding cases in which all are hydrogen atoms).

2. A condensed eight-ring aromatic compound according to claim 1, wherein the substituent is selected from halogen atoms, hydroxy groups, cyano groups, alkyl groups, alkoxy groups, aryl groups, aryloxy groups, arylamino groups, and diarylamino groups.

3. A condensed eight-ring aromatic compound according to claim 1, wherein at least one of R¹ through R¹⁸ in the structural formula (1), at least one of R¹ through R¹⁶ in the structural formula (2), or at least one of R¹ through R¹⁴ in the structural formula (3) is an aryl group.

4. A condensed eight-ring aromatic compound according to claim 1, wherein at least one of R¹ through R¹⁸ in the structural formula (1), at least one of R¹ through R¹⁶ in the structural formula (2), or at least one of R¹ through R¹⁴ in the structural formula (3) is selected from arylamino groups and diarylamino groups.

5. A condensed eight-ring aromatic compound according to claim 1, wherein in structural formula (1), R¹ through R⁸ and R¹⁰ through R¹⁷ are hydrogen atoms and R⁹ and R¹⁸ are selected from phenyl groups, phenylamino groups, and diphenylamino groups, and in the structural formula (2), R¹ through R⁶, R⁸ through R¹⁴, and R¹⁶ are hydrogen atoms and R⁷ and R¹⁵ are selected from phenyl groups, phenylamino groups and diphenylamino groups, or in the structural formula (3), R¹ through R⁵, R⁷ through R¹², and R¹⁴ are hydrogen atoms and R⁶ and R¹³ are selected from phenyl groups, phenylamino groups and diphenylamino groups.

6. A condensed eight-ring aromatic compound according to claim 1, wherein R⁹ and R¹⁸ in structural formula (1), R⁷ and R¹⁵ in structural formula (2), or R⁶ and R¹³ in structural formula (3) are the same.

7. A condensed eight-ring aromatic compound according to claim 1, wherein the condensed eight-ring aromatic compound is contained in an organic EL element.

8. A condensed eight-ring aromatic compound according to claim 3, wherein the condensed eight-ring aromatic compound is contained in at least one of an electron transporting layer and a light-emitting layer of an organic EL element.

9. A condensed eight-ring aromatic compound according to claim 4, wherein the condensed eight-ring aromatic compound is contained in at least one of a positive hole transporting layer and a light-emitting layer of an organic EL element.

10. An organic EL element comprising an organic thin-film layer including a light-emitting layer in between a positive electrode and a negative electrode, and the organic thin-film layer contains a condensed eight-ring aromatic compound,

wherein the condensed eight-ring aromatic compound has a point-symmetrical skeleton,

wherein the condensed eight-ring aromatic compound is represented by any of following structural formulas (1) through (3):

where R¹ through R¹⁸ may be the same or may be different from each other, and represent hydrogen atoms or substituents;

where R¹ through R¹⁶ may be the same or may be different from each other, and represent hydrogen atoms or substituents;

where R¹ through R¹⁴ may be the same or may be different from each other, and represent hydrogen atoms or substituents.

11. An organic EL element according to claim 10, wherein the light-emitting layer contains the condensed eight-ring aromatic compound.

12. An organic EL element according to claim 10, wherein the substituent is selected from halogen atoms, hydroxy groups, cyano groups, alkyl groups, alkoxy groups, aryl groups, aryloxy groups, arylamino groups, and diarylamino groups.

13. An organic EL element according to claim 10, wherein at least one of R¹ through R¹⁸ in the structural formula (1), at least one of R¹ through R¹⁶ in the structural formula (2), or at least one of R¹ through R¹⁴ in the structural formula (3) is an aryl group.

14. An organic EL element according to claim 10, wherein at least one of R¹ through R¹⁸ in the structural formula (1), at least one of R¹ through R¹⁶ in the structural formula (2), or at least one of R¹ through R¹⁴ in the structural formula (3) is an arylamino group.

15. An organic EL element according to claim 10, wherein at least one of R¹ through R¹⁸ in the structural formula (1), at least one of R¹ through R¹⁶ in the structural formula (2), or at least one of R¹ through R¹⁴ in the structural formula (3) is a diarylamino group.

16. An organic EL element according to claim 10, wherein the organic thin-film layer has an electron transporting layer, and the electron transporting layer contains the condensed eight-ring aromatic compound.

17. An organic EL element according to claim 16, wherein at least one of R¹ through R¹⁸ in the condensed eight-ring aromatic compound contained in the electron transporting layer is an aryl group.

18. An organic EL element according to claim 10, wherein the organic thin-film layer has a positive hole transporting layer, and the positive hole transporting layer contains the condensed eight-ring aromatic compound.

19. An organic EL element according to claim 18, wherein at least one of R¹ through R¹⁸ in the condensed eight-ring aromatic compound contained in the positive hole transporting layer is selected from arylamino groups and diarylamino groups.

20. An organic EL element according to claim 10, wherein in the structural formula (1), R¹ through R⁸ and R¹⁰ through R¹⁷ are hydrogen atoms and R⁹ and R¹⁸ are selected from phenyl groups, phenylamino groups, and diphenylamino groups, and in the structural formula (2), R¹ through R⁶, R⁸ through R¹⁴, and R¹⁶ are hydrogen atoms and R⁷ and R¹⁵ are selected from phenyl groups, phenylamino groups and diphenylamino groups, or in the structural formula (3), R¹ through R⁵, R⁷ through R¹², and R¹⁴ are hydrogen atoms and R⁶ and R¹³ are selected from phenyl groups, phenylamino groups and diphenylamino groups.

21. An organic EL element according to claim 10, wherein R⁹ and R¹⁸ in the structural formula (1), R⁷ and R¹⁵ in the structural formula (2), or R⁶ and R¹³ in the structural formula (3) are the same.

22. An organic EL element according to claim 10, wherein the light-emitting layer contains a host compound whose light absorption wavelength is at a short wavelength side of a light absorption wavelength of the condensed eight-ring aromatic compound, and whose light-emitting wavelength is in a vicinity of the light absorption wavelength of the condensed eight-ring aromatic compound.

23. A organic EL element according to claim 10, wherein the light-emitting layer contains n types of host compounds (where n represents an integer of 1 or more), and given that the n host compounds are a first host compound, a second host compound, . . . , an (n−

1) th host compound, and an nth host compound in order from the host compound with the shortest light absorption wavelength, a light-emitting wavelength of the first host compound is in a vicinity of a light absorption wavelength of the second host compound, a light-emitting wavelength of the second host compound is in a vicinity of a light absorption wavelength of a third host compound, . . . , a light-emitting wavelength of the (n−

1) th host compound is in a vicinity of a light absorption wavelength of the nth host compound, and a light-emitting wavelength of the nth host compound is in a vicinity of a light absorption wavelength of the condensed eight-ring aromatic compound.

24. An organic EL element according to claim 22, wherein a content of the host compound is 90 mol or more with respect to 1 mol of the condensed eight-ring aromatic compound.

25. An organic EL element according to claim 22, wherein the host compound is an aluminum quinoline complex (Alq) represented by the following structural formula:

26. An organic EL element according to claim 23, wherein a content of one of the n types of host compounds which has the light-emitting wavelength in the vicinity of the absorption wavelength of the condensed eight-ring aromatic compound, is 1 mol or more with respect to 1 mol of the condensed eight-ring aromatic compound.

27. An organic EL element according to claim 23, wherein the host compounds are an aluminum quinoline complex (Alq) represented by the following structural formula and a rubrene represented by the following structural formula:

28. An organic EL element according to claim 10, wherein a thickness of the light-emitting layer is 5 to 50 nm.

29. An organic EL element according to claim 10, wherein an emission wavelength is 600 to 650 nm.

30. An organic EL display comprising an organic EL element which comprises an organic thin-film layer including a light-emitting layer in between a positive electrode and a negative electrode, and the organic thin-film layer contains a condensed eight-ring aromatic compound,

wherein the condensed eight-ring aromatic compound has a point-symmetrical skeleton,

wherein the condensed eight-ring aromatic compound is represented by any of following structural formulas (1) through (3):

where R¹ through R¹⁸ may be the same or may be different from each other, and represent hydrogen atoms or substituents;

where R¹ through R¹⁶ may be the same or may be different from each other, and represent hydrogen atoms or substituents;

where R¹ through R¹⁴ may be the same or may be different from each other, and represent hydrogen atoms or substituents.

31. An organic EL display according to claim 30, wherein the organic EL display is one of a passive matrix panel and an active matrix panel, and uses the organic EL element for emitting red light.