Polycyclic aromatic compound, material for an organic device, organic electroluminescent element, display apparatus and lighting apparatus

Patent metadata

Field	Value
Publication number	US-11248009-B2
Application number	US-201916724228-A
Country	US
Kind code	B2
Filing date	Dec 21, 2019
Priority date	Dec 27, 2018
Publication date	Feb 15, 2022
Grant date	Feb 15, 2022

Abstract

A polycyclic aromatic compound in which a plurality of aromatic rings are connected by a boron atom and an oxygen atom, a sulfur atom or a selenium atom and substituted by a specific aryl such as anthracene, is useful as a material for an organic device. By the polycyclic aromatic compound, an organic EL device having at least one of efficiency and device life can be provided.

First claim

The invention claimed is:

1. A polycyclic aromatic compound represented by the following general formula (1)

wherein in the above formula (1),
X 1 and X 2 each independently represent >O, >S or >Se,
R 1 to R 11 each independently represent a hydrogen atom, an alkyl, a cycloalkyl, or an aryl that may be substituted by an alkyl or a cycloalkyl, adjacent groups among R 1 to R 11 may be bonded to each other to form an aryl ring together with ring a, ring b, or ring c, at least one hydrogen atom in the formed aryl ring may be substituted by an alkyl, a cycloalkyl, or an aryl that may be substituted by an alkyl or a cycloalkyl, and
at least one of R 1 to R 11 is independently a group represented by the following formula (Z-1),

wherein the symbol * represents a bonding position, Ar is a tricyclic or higher fused aryl, at least one hydrogen atom in the fused aryl may be substituted by an alkyl having 1 to 5 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 18 carbon atoms that may be substituted by an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, or a heteroaryl having 2 to 18 carbon atoms that may be substituted by an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, and
at least one hydrogen atom in the compound represented by the above formula (1) may be substituted by a halogen atom, a cyano or a deuterium atom.

2. The polycyclic aromatic compound described in claim 1 ,
wherein R 1 to R 11 each independently represent a hydrogen atom, an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, or an aryl having 6 to 18 carbon atoms that may be substituted by an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms, adjacent groups among R 1 to R 11 may be bonded to each other to form an aryl ring having 10 to 20 carbon atoms together with ring a, ring b, or ring c, at least one hydrogen atom in the formed aryl ring may be substituted by an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, or an aryl having 6 to 18 carbon atoms that may be substituted by an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms, and
at least one of R 1 to R 11 is independently a group represented by the above formula (Z-1).

3. The polycyclic aromatic compound described in claim 1 , wherein at least one of R 4 to R 11 is independently a group represented by the above formula (Z-1).

4. The polycyclic aromatic compound described in claim 1 , wherein Ar is independently a group represented by any one of the following formulas (Ar-1) to (Ar-12),

wherein the group represented by any one of the above formulas (Ar-1) to (Ar-12) is bonded to the group represented by the above formula (Z-1) at * in each formula,
at least one hydrogen atom in the group represented by any one of the above formulas (Ar-1) to (Ar-12) may be substituted by an alkyl having 1 to 5 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 18 carbon atoms that may be substituted by an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, or a heteroaryl having 2 to 18 carbon atoms that may be substituted by an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, and
A 1 and A 2 both may be hydrogen atoms, respectively, or may be bonded to each other to form a spiro ring.

5. The polycyclic aromatic compound described in claim 1 , wherein Ar is independently a group represented by the following formula (Ar-1-1), (Ar-1-2), (Ar-2-1), (Ar-2-2), (Ar-2-3), (Ar-3-1), (Ar-4-1), (Ar-5-1), (Ar-5-2), (Ar-5-3), (Ar-6-1), (Ar-7-1), (Ar-8-1), (Ar-9-1), (Ar-10-1), (Ar-11-1), or (Ar-12-1),

wherein in the above formulas (Ar-1-1) to (Ar-12-1), X independently represents a hydrogen atom, an alkyl having 1 to 5 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, or an aryl having 6 to 10 carbon atoms that may be substituted by an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, A 1 and A 2 both may be hydrogen atoms, respectively, or may be bonded to each other to form a spiro ring, “—Xn” in each of the formulas (Ar-1-1), (Ar-1-2), (Ar-2-1), (Ar-2-2) and (Ar-2-3) represents that n pieces of Xs are each independently bonded to any positions, and n is 1 or 2, and each of the formulas is bonded to the group represented by the above formula (Z-1) at *.

6. The polycyclic aromatic compound described in claim 1 , wherein Ar is independently a group represented by the following formula (Ar-1-1a) or (Ar-1-2a),

wherein in the above formulas (Ar-1-1a) and (Ar-1-2a), X independently represents a hydrogen atom, an alkyl having 1 to 5 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, or an aryl having 6 to 10 carbon atoms that may be substituted by an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, each of the formulas is bonded to the group represented by the above formula (Z-1) at *.

7. The polycyclic aromatic compound described in claim 1 , wherein X 1 and X 2 are each >O.

8. The polycyclic aromatic compound described in claim 1 , represented by any one of the following formula

9. A material for an organic device, comprising the polycyclic aromatic compound described in claim 1 .

10. The material for an organic device described in claim 9 , in which the material for an organic device is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin film solar cell.

11. The material for an organic device described in claim 10 , in which the material for an organic electroluminescent element is a material for a light emitting layer.

12. The material for an organic device described in claim 11 , further comprising at least one of a polycyclic aromatic compound represented by the following general formula (2) and a polycyclic aromatic compound multimer having a plurality of structures represented by the following general formula (2),

wherein in the above formula (2),
ring A, ring B and ring C each independently represent an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted by a substituent,
X 1 and X 2 each independently represent >O or >N—R, R of the >N—R represents an aryl that may be substituted by a substituent, or a heteroaryl that may be substituted by a substituent, an alkyl that may be substituted by a substituent, or a cycloalkyl that may be substituted by a substituent, and R of the >N—R may be bonded to at least one of the ring

Assignees

• Kwansei Gakuin Educational Found
• Sk Mat Jnc Co Ltd

Inventors

• Hatakeyama Takuji
• Imai Hiroyuki
• Yamaga Yuko
• Inoue Daisuke
• Tajima Akio

Classifications

• C09K2211/1011

  Condensed systems · CPC title

• C09K2211/1096

  containing other heteroatoms · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• H10K85/30

  Coordination compounds · CPC title

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title