Organic electroluminescence device and novel compound

• US 10,658,594 B2
• Filed: 03/01/2019
• Issued: 05/19/2020
• Est. Priority Date: 12/06/2017
• Status: Active Grant

• Current Assignee: Idemitsu Kosan Company Limited
• Original Assignee: Idemitsu Kosan Company Limited
• Inventors: Takahashi, Ryota, Ikeda, Hidetsugu, Seda, Keita, Nakano, Yuki
• Primary Examiner(s): Yang, Jay
• Application Number:
  US16/290,702
• Publication Number:
  US 20190194215A1
• Time in Patent Office: 445 Days
• Field of Search: None
• CPC Class Codes: C07D 487/22 in which the condensed system contains four or more hetero rings
• CPC Class Codes: C07D 491/22 in which the condensed system contains four or more hetero rings
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1018 Heterocyclic compounds
• CPC Class Codes: G09F 9/30 in which the desired character or characters are formed by combining individual elements panels comprising a number of electrodes in a single cell controlling light arriving from an independent light source, e.g. electro-optical or magneto-optical cell, G02F1/00
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 2102/00 Constructional details relating to the organic devices covered by this subclass
• CPC Class Codes: H10K 2102/103 comprising indium oxides, e.g. ITO
• CPC Class Codes: H10K 2102/351 Thickness
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/15 Hole transporting layers
• CPC Class Codes: H10K 50/16 Electron transporting layers
• CPC Class Codes: H10K 50/17 Carrier injection layers
• CPC Class Codes: H10K 50/171 Electron injection layers
• CPC Class Codes: H10K 50/81 Anodes
• CPC Class Codes: H10K 50/82 Cathodes
• CPC Class Codes: H10K 71/00 Manufacture or treatment specially adapted for the organic devices covered by this subclass
• CPC Class Codes: H10K 71/164 using vacuum deposition
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/626 : containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/633 : comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/636 : comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/6572 : comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: H10K 85/6574 : comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
• CPC Class Codes: H10K 85/6576 : comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Abstract

To provide an organic electroluminescence device having a high luminous efficiency and a novel compound that can be used as a material for an organic electroluminescence device having a high luminous efficiency.

A compound represented by the following formula (1) or (2):

• • wherein in the formulas (1) and (2),
  • one or more pairs of adjacent two or more of R₁ to R₇ and R₁₀ to R₁₆ may form a substituted or unsubstituted, saturated or unsaturated ring;
  • R₁₇, and R₁ to R₇ and R₁₀ to R₁₆ that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom, a substituted or unsubstituted aryl group including 6 to 20 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 20 ring atoms;
  • two R₁₇s may be the same or different; and
  • Ar₁ to Ar₄ are independently a substituted or unsubstituted aryl group including 6 to 20 ring carbon atoms.

Claims

1. A compound represented by the following formula (3-I):

2. A compound according to claim 1, wherein one of R₃₆ and R₃₇ is a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms and the other of R₃₆ and R₃₇ is a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms.

3. A compound according to claim 1, wherein at least one of R₃₆ and R₃₇ is a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted indolocarbazolyl group.

4. A compound according to claim 1, wherein at least one of R₃₆ and R₃₇ is a substituted or unsubstituted dibenzofuranyl group.

5. A compound according to claim 1, wherein R₁ to R₇ and R₁₀ to R₁₆ are hydrogen atoms.

6. A compound according to claim 1, wherein the substituent in the “

substituted or unsubstituted”

is selected from the group consisting of an alkyl group including 1 to 50 carbon atoms, an aryl group including 6 to 50 ring carbon atoms and a monovalent heterocyclic group including 5 to 50 ring atoms.

7. A compound according to claim 1, wherein the substituent in the “

substituted or unsubstituted”

is selected from the group consisting of an alkyl group including 1 to 18 carbon atoms, an aryl group including 6 to 18 ring carbon atoms and a monovalent heterocyclic group including 5 to 18 ring atoms.

8. A compound according to claim 1, wherein two R₁₇s are a hydrogen atom.

9. A compound according to claim 1, wherein two R₁₇s are independently a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms.

10. A compound according to claim 1, wherein two R₁₇s are independently a substituted or unsubstituted phenyl group.

11. An organic electroluminescence device comprising:

a cathode,

an anode, and

at least one organic layer disposed between the cathode and the anode, wherein

at least one layer of the at least one organic layer comprises a compound represented by the following formula (3-I);

12. An organic electroluminescence device according to claim 11, wherein one of R₃₆ and R₃₇ is a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms and the other of R₃₆ and R₃₇ is a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms.

13. An organic electroluminescence device according to claim 11, wherein at least one of R₃₆ and R₃₇ is a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted indolocarbazolyl group.

14. An organic electroluminescence device according to claim 11, wherein at least one of R₃₆ and R₃₇ is a substituted or unsubstituted dibenzofuranyl group.

15. An organic electroluminescence device according to claim 11, wherein R₁ to R₇ and R₁₀ to R₁₆ are hydrogen atoms.

16. An organic electroluminescence device according to claim 11, wherein the substituent in the “

substituted or unsubstituted”

is selected from the group consisting of an alkyl group including 1 to 50 carbon atoms, an aryl group including 6 to 50 ring carbon atoms and a monovalent heterocyclic group including 5 to 50 ring atoms.

17. An organic electroluminescence device according to claim 11, wherein the substituent in the “

substituted or unsubstituted”

is selected from the group consisting of an alkyl group including 1 to 18 carbon atoms, an aryl group including 6 to 18 ring carbon atoms and a monovalent heterocyclic group including 5 to 18 ring atoms.

18. An organic electroluminescence device according to claim 11, wherein two R₁₇s are a hydrogen atom.

19. An organic electroluminescence device according to claim 11, wherein two R₁₇s are independently a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms.

20. An organic electroluminescence device according to claim 11, wherein two R₁₇s are independently a substituted or unsubstituted phenyl group.

21. An organic electroluminescence device according to claim 11, wherein the at least one layer of the at least one organic layer is an emitting layer.

22. An electronic apparatus provided with the organic electroluminescence device according to claim 11.