Polycyclic aromatic compound for organic electroluminescent device

Patent metadata

Field	Value
Publication number	US-11600790-B2
Application number	US-201816625700-A
Country	US
Kind code	B2
Filing date	Jun 18, 2018
Priority date	Jul 7, 2017
Publication date	Mar 7, 2023
Grant date	Mar 7, 2023

Abstract

By using a polycyclic aromatic compound as a material for a light-emitting layer, formed by connecting a plurality of aromatic rings with a boron atom and an oxygen, sulfur, or selenium atom, which have been substituted by a specific aryl such as anthracene, an organic EL element having at least one of excellent quantum efficiency and element life can be provided.

First claim

The invention claimed is:

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

wherein
in the above formula (1),
X 1 and X 2 each independently represent O, S or Se,
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 each independently represents a hydrogen atom, an alkyl, or an aryl optionally substituted by an alkyl, adjacent groups of 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 aryl ring thus formed may be substituted by an alkyl,
at least one of R 1 to R 11 each independently represent a group represented by the following formula (Z-1), (Z-2), (Z-3), (Z-4), (Z-5), or (Z-6):

the group represented by each of the above formulas (Z-1) to (Z-6) is bonded to the compound represented by the above formula (1) at * in each of the formulas,
Ar's in the above formulas (Z-1) to (Z-6) each independently represent a group represented by the following formula (Ar-1), (Ar-2), (Ar-3), (Ar-4), (Ar-5), (Ar-6), (Ar-7), (Ar-8), (Ar-9), (Ar-10), (Ar-11), or (Ar-12):

the group represented by each of the above formulas (Ar-1) to (Ar-12) is bonded to the group represented by each of the above formulas (Z-1) to (Z-6) at * in each of the formulas,
in the above formulas (Ar-1) to (Ar-12), X's each independently represent a hydrogen atom, an alkyl having 1 to 4 carbon atoms, an aryl having 6 to 18 carbon atoms optionally substituted by an alkyl having 1 to 4 carbon atoms, or a heteroaryl having 2 to 18 carbon atoms optionally substituted by an alkyl having 1 to 4 carbon atoms, A 1 and A 2 both represent hydrogen atoms or may be bonded to each other to form a spiro ring, “—Xn” in formulas (Ar-1) and (Ar-2) indicates that nX's are each independently bonded to an arbitrary position, n represents an integer of 1 to 4, and
at least one hydrogen atom in the compound represented by the above formula (1) may be substituted by a deuterium atom.

2. The polycyclic aromatic compound according to claim 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 having 1 to 12 carbon atoms, or an aryl having 6 to 24 carbon atoms optionally substituted by an alkyl having 1 to 12 carbon atoms, adjacent groups of 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 aryl ring thus formed may be substituted by an alkyl having 1 to 12 carbon atoms,
one or two of R 1 to R 11 each independently represent a group represented by the above formula (Z-1), (Z-2), (Z-3), (Z-4), (Z-5), or (Z-6),
Ar's in the above formulas (Z-1) to (Z-6) each independently represent a group represented by the above formula (Ar-1), (Ar-2), (Ar-3), (Ar-4), (Ar-5), (Ar-6), (Ar-7), (Ar-8), (Ar-9), (Ar-10), (Ar-11), or (Ar-12),
in the above formulas (Ar-1) to (Ar-12), X's each independently represent a hydrogen atom, an alkyl having 1 to 4 carbon atoms, an aryl having 6 to 18 carbon atoms optionally substituted by an alkyl having 1 to 4 carbon atoms, or a heteroaryl having 4 to 16 carbon atoms optionally substituted by an alkyl having 1 to 4 carbon atoms, A 1 and A 2 both represent hydrogen atoms or may be bonded to each other to form a spiro ring, “—Xn” in formulas (Ar-1) and (Ar-2) indicates that nX's are each independently bonded to an arbitrary position, n represents an integer of 1 to 4, and
at least one hydrogen atom in the compound represented by the above formula (1) may be substituted by a deuterium atom.

3. The polycyclic aromatic compound according to claim 1 , which is represented by any one of the following formulas:

4. The polycyclic aromatic compound according to claim 1 , wherein
in the above formula (1),
X 1 and X 2 each represent O,
R 1 to R 11 each independently represent a hydrogen atom, an alkyl having 1 to 6 carbon atoms, or an aryl having 6 to 18 carbon atoms optionally substituted by an alkyl having 1 to 6 carbon atoms, adjacent groups of R 1 to R 11 may be bonded to each other to form an aryl ring having 10 to 18 carbon atoms together with ring a, ring b, or ring c, at least one hydrogen atom in the aryl ring thus formed may be substituted by an alkyl having 1 to 6 carbon atoms,
one or two of R 1 to R 11 each independently represent a group represented by the above formula (Z-1), (Z-2), (Z-3), (Z-4), (Z-5), or (Z-6),
Ar's in the above formulas (Z-1) to (Z-6) each independently represent a group represented by the following formula (Ar-1-1), (Ar-1-2), (Ar-2-1), (Ar-2-2), (Ar-2-3), (Ar-3), (Ar-4-1), (Ar-5-1), (Ar-5-2), (Ar-5-3), (Ar-6), (Ar-7), (Ar-8), (Ar-9), (Ar-10), (Ar-11), or (Ar-12):

in the above formulas (Ar-1-1) to (Ar-12), X's each independently represent a hydrogen atom, an alkyl having 1 to 4 carbon atoms, or an aryl having 6 to 10 carbon atoms, A 1 and A 2 both represent hydrogen atoms or may be bonded to each other to form a spiro ring, “—Xn” in formulas (Ar-1-1), (Ar-1-2), (Ar-2-1), (Ar-2-2), and (Ar-2-3) indicates that nX's are each independently bonded to an arbitrary position, n represents an integer of 1 or 2.

5. A material for an organic device, comprising the polycyclic aromatic compound according to claim 1 .

6. The material for an organic device according to claim 5 , wherein 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.

7. The material for an organic electroluminescent element according to claim 6 , which is a material for a light emitting layer.

8. The material for a light emitting layer according to claim 7 , wherein further comprising at least one of a polycyclic aromatic compound represented by the following general formula (2) and a multimer having a plurality of structures with each structure of the plurality of structures represented by the following general formula (2):

wherein
In the above formula (2),
ring A, ring B and ring C

Assignees

• Kwansei Gakuin Educational Found
• Sk Mat Jnc Co Ltd

Inventors

• Hatakeyama Takuji
• Tajima Akio
• Mizutani Akihide
• Baba Daisuke
• Yamaga Yuko

Classifications

• H10K10/40

  Organic transistors · CPC title

• H10K50/12

  comprising dopants · CPC title

• H10K85/657

  Polycyclic condensed heteroaromatic hydrocarbons · CPC title

• H10K85/658

  Organoboranes · CPC title

• C07F9/65685

  the ring phosphorus atom being part of a phosphine oxide or thioxide · CPC title