Polycyclic aromatic compound and light emitting layer-forming composition

Patent metadata

Field	Value
Publication number	US-11637250-B2
Application number	US-202016860261-A
Country	US
Kind code	B2
Filing date	Apr 28, 2020
Priority date	Mar 9, 2015
Publication date	Apr 25, 2023
Grant date	Apr 25, 2023

Abstract

The present invention addresses the problem of providing a polycyclic aromatic compound which has improved solubility in solvents, film formability, wet coatability and in-plane orientation. The above-described problem is solved by a composition for forming a light emitting layer, which contains, as a first component, at least one compound selected from the group consisting of compounds represented by general formula (A-1) and compounds represented by general formula (A-2), as a second component, at least one compound that has a triplet energy (ET) of 1.8-3.0 eV, and as a third component, at least one organic solvent.In the formulae, R represents a hydrogen atom, an aryl group, a heteroaryl group, a diarylamino group, a diheteroarylamino group or an aryl heteroarylamino group.

First claim

The invention claimed is:

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

in general formula (A-1),
R 1 to R 11 each independently represent a hydrogen atom, an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, or an aryloxy, while at least one hydrogen atom in these may be further substituted by an aryl, a heteroaryl, or a diarylamino,
adjacent groups among R 1 to R 11 may be bonded to each other to form an aryl ring or a heteroaryl ring together with ring a, ring b, or ring c, at least one hydrogen atom in the ring thus formed may be substituted by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, or an aryloxy, at least one hydrogen atom in these may be further substituted by an aryl, a heteroaryl, or a diarylamino,
at least one hydrogen atom in a compound represented by the above formula (A-1) 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, at least one hydrogen atom in a compound represented by the above formula (A-1) may be further substituted by a halogen atom or a deuterium atom,
any —CH 2 — in the alkyl may be substituted by —O— or —Si(CH 3 ) 2 —, any —CH 2 — excluding —CH 2 -directly bonded to the compound represented by the above formula (A-1) in the alkyl may be substituted by an arylene having 6 to 24 carbon atoms, and any hydrogen atom in the alkyl may be substituted by a fluorine atom

in general formula (FG-1),
R's each independently represent 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's each independently represent an integer of 0 to 5, and
p's each independently represent an integer of 1 to 5

in general formula (FG-2),
R's each independently represent 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's each independently represent an integer of 0 to 4, and
n's each independently represent an integer of 0 to 5.

2. The compound of claim 1 , in which
in the above formula (A-1),
R 1 to R 11 each independently represent a hydrogen atom, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms or a diarylamino (the aryl is an aryl having 6 to 12 carbon atoms), at least one hydrogen atom in these may be further substituted by an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms or a diarylamino (the aryl is an aryl having 6 to 12 carbon atoms),
adjacent groups among R 1 to R 11 may be bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with ring a, ring b, or ring c, at least one hydrogen atom in the ring thus formed may be substituted by an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms or a diarylamino (the aryl is an aryl having 6 to 12 carbon atoms), at least one hydrogen atom in these may be further substituted by an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms or a diarylamino (the aryl is an aryl having 6 to 12 carbon atoms), and
at least one hydrogen atom in a compound represented by the above formula (A-1) 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, at least one hydrogen atom in a compound represented by the above formula (A-1) may be further substituted by a halogen atom or a deuterium atom.

3. The compound of claim 1 , in which
in the above formula (A-1),
R 1 to R 11 each independently represent any one selected from the group consisting of a hydrogen atom and 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-1) at *, and

at least one hydrogen atom in a compound represented by the above formula (A-1) 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.

4. The compound of claim 1 , in which
a compound represented by the above formula (A-1) is a compound represented by the following formula (1-1-z), (1-49-z), (1-91-z), (1-100-z), (1-152-z), (1-176-z), (1-1048-z), (1-1049-z), (1-1050-z), (1-1069-z), (1-1101-z), (1-1102-z), or (1-1103-z)

z's in the above formulas each represent a hydrogen atom, 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 not all z's represent hydrogen atoms.

5. The compound of claim 1 , in which
in the above formula (FG-1), m and n each represent 0, and p represents an integer of 1 to 3, and
in the formula (FG-2), m and n each represent 0.

6. The compound of claim 1 , in which at least one hydrogen atom in a compound represented by the above formula (A-1) is substituted by a group represented by the above formula (FG-1).

Assignees

• Kwansei Gakuin Educational Found
• Sk Mat Jnc Co Ltd

Inventors

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

Classifications

• H10K85/658 Primary

  Organoboranes · CPC title

• H10K85/322

  comprising boron · CPC title

• C07F5/02 Primary

  Boron compounds · CPC title

• H10K2101/10

  Triplet emission · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title