Organic electroluminescence device and novel compound

• US 10,672,989 B2
• Filed: 11/27/2018
• Issued: 06/02/2020
• 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:
  US16/201,984
• Publication Number:
  US 20190221747A1
• Time in Patent Office: 553 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

Disclosed is a compound useful as a material for an organic electroluminescence device with high luminous efficiency. A compound is represented by the following formula (1) or (2):

Claims

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

2. A compound according to claim 1, which is represented by the following formula (1-1) or (2-1):

3. A compound according to claim 1, wherein Ar₁ to Ar₄ are independently a substituted or unsubstituted phenyl group.

4. A compound according to claim 1, wherein two R₁₇ are independently a substituted or unsubstituted aryl group including 6 to 20 ring carbon atoms.

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

6. A compound according to claim 1, wherein two R₁₇s are hydrogen atoms.

7. A compound according to claim 1, wherein R₅ to R₇ and R₁₄ to R₁₆ are hydrogen atoms.

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

substituted or unsubstituted”

is selected from the group consisting of an alkyl group including 1 to 20 carbon atoms, an aryl group including 6 to 20 ring carbon atoms, and a monovalent heterocyclic group including 5 to 20 ring atoms.

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

substituted or unsubstituted”

is an alkyl group including 1 to 5 carbon atoms.

10. A compound according to claim 2, wherein Ar₁ to Ar₄ are independently a substituted or unsubstituted phenyl group;

and

two R₁₇s are hydrogen atoms.

11. A compound according to claim 2, wherein Ar₁ to Ar₄ are independently a substituted or unsubstituted phenyl group;

two R₁₇s are independently a substituted or unsubstituted aryl group including 6 to 20 ring carbon atoms;

R₅ to R₇ and R₁₄ to R₁₆ are hydrogen atoms; and

a substituent in the “

substituted or unsubstituted”

is selected from the group consisting of an alkyl group including 1 to 20 carbon atoms, an aryl group including 6 to 20 ring carbon atoms, and a monovalent heterocyclic group including 5 to 20 ring atoms.

12. A compound according to claim 2, wherein Ar₁ to Ar₄ are independently a substituted or unsubstituted phenyl group;

two R₁₇s are independently a substituted or unsubstituted phenyl group;

R₅ to R₇ and R₁₄ to R₁₆ are hydrogen atoms; and

a substituent in the “

substituted or unsubstituted”

is an alkyl group including 1 to 5 carbon atoms.

13. 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 (1) or (2);

14. The organic electroluminescence device according to claim 13, wherein the compound represented by the formula (1) or (2) is represented by the following formula (1-1) or (2-1):

15. The organic electroluminescence device according to claim 13, wherein Ar₁ to Ar₄ are independently a substituted or unsubstituted phenyl group.

16. The organic electroluminescence device according to claim 13, wherein two R₁₇s are independently a substituted or unsubstituted aryl group including 6 to 20 ring carbon atoms.

17. The organic electroluminescence device according to claim 13, wherein two R₁₇s are independently a substituted or unsubstituted phenyl group.

18. The organic electroluminescence device according to claim 13, wherein two R₁₇s are hydrogen atoms.

19. The organic electroluminescence device according to claim 13, wherein R₅ to R₇ and R₁₄ to R₁₆ are hydrogen atoms.

20. The organic electroluminescence device according to claim 13, wherein a substituent in the “

substituted or unsubstituted”

is selected from the group consisting of an alkyl group including 1 to 20 carbon atoms, an aryl group including 6 to 20 ring carbon atoms, and a monovalent heterocyclic group including 5 to 20 ring atoms.

21. The organic electroluminescence device according to claim 13, wherein a substituent in the “

substituted or unsubstituted”

is an alkyl group including 1 to 5 carbon atoms.

22. The organic electroluminescence device according to claim 14, wherein Ar₁ to Ar₄ are independently a substituted or unsubstituted phenyl group;

and

two R₁₇s are hydrogen atoms.

23. The organic electroluminescence device according to claim 14, wherein Ar₁ to Ar₄ are independently a substituted or unsubstituted phenyl group;

two R₁₇s are independently a substituted or unsubstituted aryl group including 6 to 20 ring carbon atoms;

R₅ to R₇ and R₁₄ to R₁₆ are hydrogen atoms; and

a substituent in the “

substituted or unsubstituted”

is selected from the group consisting of an alkyl group including 1 to 20 carbon atoms, an aryl group including 6 to 20 ring carbon atoms, and a monovalent heterocyclic group including 5 to 20 ring atoms.

24. The organic electroluminescence device according to claim 14, wherein Ar₁ to Ar₄ are independently a substituted or unsubstituted phenyl group;

two R₁₇s are independently a substituted or unsubstituted phenyl group;

R₅ to R₇ and R₁₄ to R₁₆ are hydrogen atoms; and

a substituent in the “

substituted or unsubstituted”

is an alkyl group including 1 to 5 carbon atoms.

25. The organic electroluminescence device according to claim 13, wherein the at least one layer of the at least one organic layer is an emitting layer.

26. An electronic apparatus provided with the organic electroluminescence device according to claim 13.