FUSED HETEROCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE

• US 20090121625A1
• Filed: 07/31/2007
• Published: 05/14/2009
• Est. Priority Date: 08/04/2006
• Status: Active Grant

• Current Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Original Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Inventors: Yamada, Naoki, Okada, Shinjiro, Ohrui, Hiroki, Muratsubaki, Masanori, Senoo, Akihiro
• Granted Patent: US 8,072,137 B2
• Time in Patent Office: Days
• US Class Current: 313/504
• CPC Class Codes: C07D 221/18 Ring systems of four or more rings
• CPC Class Codes: C07D 239/70 condensed with carbocyclic rings or ring systems
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• 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 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/633 comprising polycyclic condensed aromatic 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

Abstract

To provide a material for an organic light emitting device showing a light emission hue with an extremely good purity and outputting light having high luminance and a long lifetime with high efficiency, the present invention relates to a fused heterocyclic compound having at least one partial structure represented by the following general formula [1].

Claims

1. A fused heterocyclic compound comprising at least one partial structure represented by the following general formula [1]:

wherein;

X₁ to X₁₀ each represent a carbon atom having a substituent R or a nitrogen atom, the carbon atom or the nitrogen atom forming a ring, R represents a hydrogen atom, a halogen atom, a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, a substituted or unsubstituted fused polycyclic heterocyclic group and a cyano group, or a single bond provided that at least one of X₁ to X₁₀ represents a nitrogen atom, and when a plurality of carbon atoms each having the substituent R are present, R'"'"'s may be independently identical to or different from each other, and adjacent substituents may form a ring structure; and

R₁ and R₂ each represent a halogen atom, a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, a substituted or unsubstituted fused polycyclic heterocyclic group and a cyano group, or a single bond, and R₁ and R₂ may be identical to or different from each other.

2. A fused heterocyclic compound according to claim 1, wherein R represents a hydrogen atom, a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group and a substituted or unsubstituted fused polycyclic heterocyclic group, or a single bond, and R₁ and R₂ each represent a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group and a substituted or unsubstituted fused polycyclic heterocyclic group, or a single bond.

3. A fused heterocyclic compound according to claim 1, wherein none of R, R₁, and R₂ represents a single bond.

4. A fused heterocyclic compound according to claim 1, wherein the compound is represented by the following general formula [2]:

wherein;

X₁ to X₁₀ each represent a carbon atom having a substituent R or a nitrogen atom, the carbon atom or the nitrogen atom forming a ring, at least one of X₁ to X₁₀ represents a nitrogen atom, and when a plurality of carbon atoms each having the substituent R are present, R'"'"'s may be independently identical to or different from each other;

Y represents a single bond, or an n-valent linking group derived from a substituted or unsubstituted alkane, a substituted or unsubstituted alkene, a substituted or unsubstituted alkyne, a substituted or unsubstituted amine, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted heterocyclic ring, a substituted or unsubstituted fused polycyclic aromatic ring, or a substituted or unsubstituted fused polycyclic heterocyclic ring;

R₁ and R₂ each represent a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, and a substituted or unsubstituted fused polycyclic heterocyclic group, and R₁ and R₂ may be identical to or different from each other;

Y is bonded to any one of a carbon atom represented by any one of X₁ to X₁₀, R₁, and R₂; and

n represents an integer of 2 or more to 10 or less.

5. A fused heterocyclic compound according to claim 1, wherein the compound is represented by the following general formula [3]:

wherein;

Z represents a ring structure;

X₁ to X₈ each represent a carbon atom having a substituent R or a nitrogen atom, the carbon atom or the nitrogen atom forming a ring, at least one of X₁ to X₈ represents a nitrogen atom, R represents a hydrogen atom, a halogen atom, or a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, a substituted or unsubstituted fused polycyclic heterocyclic group and a cyano group, and when a plurality of carbon atoms each having the substituent R are present, R'"'"'s may be independently identical to or different from each other; and

R₁ and R₂ each represent a halogen atom, or a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, a substituted or unsubstituted fused polycyclic heterocyclic group and a cyano group, and R₁ and R₂ may be identical to or different from each other.

6. A fused heterocyclic compound according to claim 5, wherein the compound is represented by the following general formula [4]:

wherein;

X₁ to X₈ each represent a carbon atom having a substituent R or a nitrogen atom, the carbon atom or the nitrogen atom forming a ring, at least one of X₁ to X₈ represents a nitrogen atom, R represents a hydrogen atom, a halogen atom, or a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, a substituted or unsubstituted fused polycyclic heterocyclic group and a cyano group; and

R₁ to R₁₀ each represent a halogen atom, or a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, a substituted or unsubstituted fused polycyclic heterocyclic group and a cyano group, and R₁ to R₁₀ may be identical to or different from one another.

7. A fused heterocyclic compound according to claim 5, wherein the compound is represented by the following general formula [5]:

wherein;

X₁ to X₁₈ each represent a carbon atom having a substituent R or a nitrogen atom, the carbon atom or the nitrogen atom forming a ring, at least one of X₁ to X₁₈ represents a nitrogen atom, R represents a hydrogen atom, a halogen atom, or a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, a substituted or unsubstituted fused polycyclic heterocyclic group and a cyano group, and when a plurality of carbon atoms each having the substituent R are present, R'"'"'s may be independently identical to or different from each other; and

R₁ to R₄ each represent a halogen atom, or a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, a substituted or unsubstituted fused polycyclic heterocyclic group and a cyano group, and R₁ to R₄ may be identical to or different from one another.

8. A fused heterocyclic compound according to claim 1, wherein X₁ or X₂ represents a nitrogen atom.

9. A fused heterocyclic compound according to claim 7, wherein at least one of X₁, X₂, X₁₇, and X₁₈ represents a nitrogen atom.

10. An organic light emitting device comprising:

a pair of electrodes constituted of an anode and a cathode at least one of which is formed of a transparent or semitransparent electrode material; and

a layer containing an organic compound, the layer being interposed between the pair of electrodes,

wherein the layer containing an organic compound contains the fused heterocyclic compound according to claim 1.

11. An organic light emitting device according to claim 10, wherein the layer containing the fused heterocyclic compound comprises at least two kinds of compounds of a host and a guest.

12. An organic light emitting device according to claim 11, wherein the guest comprises the fused heterocyclic compound, and the host comprises a compound having an energy gap larger than an energy gap of the fused heterocyclic compound.

13. An organic light emitting device according to claim 11, wherein the guest has a reduction potential higher than that of the host by 0.3 V or more.

14. An organic light emitting device according to claim 10, wherein the layer containing the fused heterocyclic compound comprises at least one layer having a light emitting region.

15. An organic light emitting device according to claim 14, wherein the at least one layer having the light emitting region comprises a light emitting layer.