Polycyclic aromatic compound and light emitting layer-forming composition

Patent metadata

Field	Value
Publication number	US-2020259089-A1
Application number	US-202016860261-A
Country	US
Kind code	A1
Filing date	Apr 28, 2020
Priority date	Mar 9, 2015
Publication date	Aug 13, 2020
Grant date	—

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 (E T ) 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

1 .- 18 . (canceled)

19 . 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.

20 . A compound represented by the following general formula (A-2)

in general formula (A-2),
R 1 to R 16 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 16 may be bonded to each other to form an aryl ring or a heteroaryl ring together with ring a, ring b, ring c, or ring d, 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-2) is substituted by a group represented by the following 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-2) 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 a compound represented by the above formula (A-2) 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.

21 . The compound of claim 19 , 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

Assignees

• Kwansei Gakuin Educational Found
• Jnc Corp

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

• C07F5/05

  Cyclic compounds having at least one ring containing boron but no carbon in the ring · CPC title

• C09K2211/1096

  containing other heteroatoms · CPC title