Polycyclic aromatic compound and light emission layer-forming composition

Patent metadata

Field	Value
Publication number	US-11807656-B2
Application number	US-202117459550-A
Country	US
Kind code	B2
Filing date	Aug 27, 2021
Priority date	Mar 25, 2015
Publication date	Nov 7, 2023
Grant date	Nov 7, 2023

Abstract

The objective of the invention is to provide a polycyclic aromatic compound in which solubility to a solvent, film formability, wet coatability, thermal stability, and in-plane orientation are improved. This objective is achieved by alight emission layer-forming composition comprising: as a first component, at least one type of dopant material selected from the group consisting of polycyclic aromatic compounds represented by general formula (A) and polycyclic aromatic oligomer compounds including a plurality of structures represented by general formula (A); as a second component, a specific low-molecular-weight host material; and, as a third component, at least one type of organic solvent. In formula (A), ring A, ring B, and ring C each independently represent an aryl ring or a hetero aryl ring, Y 1 is B, and X 1 and X 2 each independently represent O or N—R wherein at least one of X 1 and X 2 is N—R.

First claim

The invention claimed is:

1. A polycyclic aromatic compound represented by the following general formula (A) or a polycyclic aromatic multimer compound having a plurality of structures represented by the following general formula (A):

wherein the above formula (A),
each of ring A, ring B, and ring C independently represents an aryl ring or a heteroaryl ring, at least one of these rings is a heteroaryl ring selected from the group consisting of an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a benzothiophene ring, a dibenzothiophene ring, and a thianthrene ring, and at least one hydrogen atom in these rings may be substituted,
Y 1 represents B,
each of X 1 and X 2 independently represents O or N—R, while at least one of X 1 and X 2 represents N—R, R of the N—R is an optionally substituted aryl, an optionally substituted heteroaryl or an optionally substituted alkyl,
at least one hydrogen atom in a compound or a structure represented by the above formula (A) is substituted by a group represented by the following general formula (FG-1), a group represented by the following general formula (FG-2), or an alkyl having 7 to 24 carbon atoms, and any hydrogen atom in the alkyl may be substituted by a fluorine atom, and at least one hydrogen atom in the compound or structure represented by the above formula (A) may be further substituted by a halogen atom or a deuterium atom;

wherein the above formula (FG-1),
each of R's independently represents a fluorine atom, a trimethylsilyl, a trifluoromethyl, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, any —CH 2 — in the alkyl may be substituted by —O—, any —CH 2 -excluding —CH 2 — directly bonded to a phenyl or a phenylene in the alkyl may be substituted by an arylene having 6 to 24 carbon atoms, at least one hydrogen atom in the cycloalkyl may be substituted by an alkyl having 1 to 24 carbon atoms or an aryl having 6 to 12 carbon atoms,
when two adjacent R's each represent an alkyl or a cycloalkyl, these R's may be bonded to each other to form a ring,
m's each independently represent an integer of 0 to 4,
n represents an integer of 0 to 5, and
p represents an integer of 1 to 5;

wherein in the above formula (FG-2),
each of R's independently represents a fluorine atom, a trimethylsilyl, a trifluoromethyl, an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, or an aryl having 6 to 12 carbon atoms, any —CH 2 — in the alkyl may be substituted by —O—, any —CH 2 -excluding —CH 2 — directly bonded to a phenyl or a phenylene in the alkyl may be substituted by an arylene having 6 to 24 carbon atoms, at least one hydrogen atom in the cycloalkyl may be substituted by an alkyl having 1 to 24 carbon atoms or an aryl having 6 to 12 carbon atoms, at least one hydrogen atom in the aryl may be substituted by an alkyl having 1 to 24 carbon atoms,
when two adjacent R's each represent an alkyl or a cycloalkyl, these R's may be bonded to each other to form a ring,
m represents an integer of 0 to 4, and
n's each independently represent an integer of 0 to 5.

2. The polycyclic aromatic compound or the multimer thereof according to claim 1 , wherein
each of the ring A, ring B, and ring C independently represents an aryl ring or a heteroaryl ring, at least one of these rings is a heteroaryl ring selected from the group consisting of an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a benzothiophene ring, a dibenzothiophene ring, and a thianthrene ring, while at least one hydrogen atom in these rings may be substituted by a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkoxy, or a substituted or unsubstituted aryloxy, and each of these rings has a 5-membered or 6-membered ring sharing a bond with a fused bicyclic structure at the center of the above formula (A) constituted by Y 1 , X 1 , and X 2 ,
Y 1 represents B,
each of X 1 and X 2 independently represents O or N—R, while at least one of X 1 and X 2 represents N—R, R of the N—R is an aryl optionally substituted by an alkyl, a heteroaryl optionally substituted by an alkyl, or alkyl optionally substituted by an alkyl,
at least one hydrogen atom in a compound or a structure represented by the above formula (A) is substituted by a group represented by the above formula (FG-1), a group represented by the above formula (FG-2), or an alkyl having 7 to 24 carbon atoms, and any hydrogen atom in the alkyl may be substituted by a fluorine atom, and at least one hydrogen atom in the compound or structure represented by the above formula (A) may be further substituted by a halogen atom or a deuterium atom.

3. The polycyclic aromatic compound or the multimer thereof according to claim 1 , wherein the polycyclic aromatic multimer compound is a dimer compound or a trimer compound having two or three structures represented by the above formula (A).

4. The polycyclic aromatic compound or the multimer thereof according to claim 1 , wherein the polycyclic aromatic multimer compound is a dimer compound having two structures represented by the above formula (A).

5. The polycyclic aromatic compound or the multimer thereof according to claim 1 , wherein each X 1 and X 2 represents N—R.

6. The polycyclic aromatic compound or the multimer thereof according to claim 1 , wherein X 1 represents O, and X 2 represents N—R.

7. The polycyclic aromatic compound or the multimer thereof according to claim 1 , wherein
at least one hydrogen atom in the ring A, the ring B, and the ring C may be substituted by any one of groups represented by the following formulas (RG-1) to (RG-10), and
the groups represented by the following formulas (RG-1) to (RG-10) are each bonded to the above formula (A) at *

8. The polycyclic aromatic compound or the multimer thereof according to claim 1 , wherein
in the above formula (FG-1), each of m and n represents 0, and p represents an integer from 1 to 3, and
in the formula (FG-2), each m and n represents 0.

9. The polycyclic aromatic compound or the multimer thereof according to claim 1 , wherein at least one hydrogen atom in a compound or a structure represe

Assignees

• Kwansei Gakuin Educational Found
• Sk Mat Jnc Co Ltd

Inventors

• Hatakeyama Takuji
• Kondo Yasuhiro
• Nakamoto Keiichi
• Yanai Motoki

Classifications

• C07F5/02 Primary

  Boron compounds · CPC title

• H10K85/658 Primary

  Organoboranes · CPC title

• C07F5/027 Primary

  Organoboranes and organoborohydrides · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title