Organic compound and organic light-emitting device

Patent metadata

Field	Value
Publication number	US-9911921-B2
Application number	US-201414766298-A
Country	US
Kind code	B2
Filing date	Apr 3, 2014
Priority date	Apr 3, 2013
Publication date	Mar 6, 2018
Grant date	Mar 6, 2018

Abstract

Provided is an organic light-emitting device capable of outputting light with high efficiency and high luminance. The organic light-emitting device includes an anode, a cathode, an emission layer placed between the anode and the cathode, and an organic compound layer placed between the anode and the emission layer, in which the organic compound layer contains the following compound A and compound B: [Compound A] an organic compound free of a nitrogen atom and a metal atom, the compound having SP 2 carbon atoms and SP 3 carbon atoms, and having a ratio of the number of the SP 3 carbon atoms to the number of the SP 2 carbon atoms of 40% or more; and [Compound B] a compound having a tertiary amine structure.

First claim

The invention claimed is:

1. An organic compound having general formula [3]:

wherein, in the general formula [3], Z 2 represents a fluoren-4-yl group, a phenanthryl group, a triphenylenyl group, an aliphatic condensed polycyclic group, a carbon atom, or an oxygen atom, and when Z 2 represents a fluoren-4-yl group, a phenanthryl group, a triphenylenyl group, or an aliphatic condensed polycyclic group, Z 2 can be substituted with a substituent selected from the group consisting of an alkyl group, an alkoxy group, an aryl group, and a halogen atom,
wherein, in the general formula [3], R 1 to R 9 each represent a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom, provided that at least two of substituents represented by R 1 to R 9 comprise alkyl groups,
wherein, in the general formula [3], m represents an integer of from 1 to 6, provided that when Z 2 represents a carbon atom, m represents 4, and when Z 2 represents an oxygen atom, m represents 2, and when m represents 2 or more, structures in parentheses may be identical to or different from each other.

2. The organic compound according to claim 1 , wherein Z 2 represents an aliphatic condensed polycyclic group, carbon atom, or oxygen atom and the aliphatic condensed polycyclic group can be substituted by a substituent selected from the group consisting of an alkyl group, an alkoxy group, an aryl group, and a halogen atom.

3. The organic compound according to claim 1 , wherein the compound has general formula [5]:

wherein, in the general formula [5], Z 11 represents a fluoren-4-yl group, a phenanthryl group, a triphenylenyl group, an aliphatic condensed polycyclic group, a carbon atom, or an oxygen atom, and when Z 11 represents a fluoren-4-yl group, a phenanthryl group, a triphenylenyl group, or an aliphatic condensed polycyclic group, Z 11 can be substituted by a substituent selected from the group consisting of an alkyl group, an alkoxy group, an aryl group, and a halogen atom,
wherein, in the general formula [5], R 2 , R 6 , R 8 , and R 9 each represent an alkyl group or an alkoxy group, and may be identical to or different from one another,
wherein, in the general formula [5], m represents an integer of from 1 to 6, provided that when Z 11 represents a carbon atom, m represents 4, and when Z 11 represents an oxygen atom, m represents 2, and when m represents 2 or more, structures in parentheses may be identical to or different from each other.

4. The organic compound according to claim 3 , wherein Z 11 represents an aliphatic condensed polycyclic group, carbon atom, or oxygen atom and the aliphatic condensed polycyclic group can be substituted with a substituent selected from the group consisting of an alkyl group, an alkoxy group, an aryl group, and a halogen atom.

5. The organic compound according to claim 3 , wherein the compound has general formula [6]:

wherein, in the general formula [6], R 12 , R 16 , R 18 , R 19 , R 21 , R 24 , R 27 , and R 28 each represent an alkyl group or an alkoxy group, and may be identical to or different from one another.

6. The organic compound according to claim 1 , wherein the compound has SP 2 carbon atoms and SP 3 carbon atoms and has a ratio of the number of the SP 3 carbon atoms to the number of the SP 2 carbon atoms of 40% or more.

7. An organic light-emitting device comprising:
an anode;
a cathode;
an emission layer placed between the anode and the cathode; and
an organic compound layer placed between the anode and the emission layer, wherein the organic compound layer contains the organic compound according to claim 1 .

8. An organic light-emitting device comprising:
an anode;
a cathode;
an emission layer placed between the anode and the cathode; and
an organic compound layer placed between the cathode and the emission layer,
wherein the organic compound layer contains the organic compound according to claim 1 .

9. An organic light-emitting device comprising:
an anode;
a cathode; and
an emission layer placed between the anode and the cathode,
wherein the emission layer contains the organic compound according to claim 1 .

10. A device comprising:
an anode;
a cathode;
an emission layer placed between the anode and the cathode; and
an organic compound layer placed between the anode and the emission layer,
wherein the organic compound layer contains compound A and compound B, compound A being an organic compound free of a nitrogen atom and a metal atom, the compound having SP 2 carbon atoms and SP 3 carbon atoms, and compound B being a compound having a tertiary amine structure,
wherein compound A has general formula [3]:

wherein, in the general formula [3], Z 2 represents a naphthyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, an aliphatic condensed polycyclic group, a carbon atom, or an oxygen atom, and when Z 2 represents a naphthyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, or an aliphatic condensed polycyclic group, Z 2 can be substituted with a substituent selected from the group consisting of an alkyl group, an alkoxy group, an aryl group, and a halogen atom,
wherein, in the general formula [3], R 1 to R 9 each represent a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom, provided that at least two of substituents represented by R 1 to R 9 comprise alkyl groups,
wherein, in the general formula [3], m represents an integer of from 1 to 6, provided that when Z 2 represents a carbon atom, m represents 4, and when Z 2 represents an oxygen atom, m represents 2, and when m represents 2 or more, structures in parentheses may be identical to or different from each other, and
with the proviso that Z 2 , m and R 1 -R 9 are selected so that compound A has a ratio of the number of the SP 3 carbon atoms to the number of the SP 2 carbon atoms of 40% or more.

11. The device according to claim 10 , wherein the ratio of the number of the SP 3 carbon atoms of the compound A to the number of the SP 2 carbon atoms of the compound A is 80% or more.

12. The device according to claim 10 , wherein a ratio of the compound B in the organic compound layer with reference to a total of the compound A and the compound B is from 10 wt % to 90 wt %.

13. The device according to claim 10 , wherein a ratio of the compound B in the organic compound layer with reference to a total of the compound A and the compound B is from 20 wt % to 70 wt %.

14. The device according to claim 10 , wherein compound A has general formula [5]:

wherein, in the general formula [5], Z 11 represents a naphthyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, an aliphatic condensed polycyclic group, a carbon atom, or an oxygen atom, and when Z 11 represents a naphthyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, or an aliphatic condensed polycyclic group, Z 11 may be substituted with a substituent selected from the group consisting of an alkyl group, an alkoxy group, an aryl group, and a halogen atom,

Assignees

• Canon Kk

Inventors

• Yamada Naoki
• Kamatani Jun
• Saitoh Akihito
• Nishide Yosuke
• Muratsubaki Masanori
• Ishii Ryuji
• Ishige Koichi
• Ito Takayuki
• Kajimoto Norifumi
• Mizuno Nobutaka

Classifications

• C07C2601/14

  The ring being saturated · CPC title

• C07C2603/48

  Chrysenes; Hydrogenated chrysenes · CPC title

• C07C13/567

  with a fluorene or hydrogenated fluorene ring system · CPC title

• C07C43/275 Primary

  having all ether-oxygen atoms bound to carbon atoms of six-membered aromatic rings · CPC title

• C07C2603/26

  Phenanthrenes; Hydrogenated phenanthrenes · CPC title