Polycyclic aromatic compound and light emission layer-forming composition

Patent metadata

Field	Value
Publication number	US-10689402-B2
Application number	US-201615559912-A
Country	US
Kind code	B2
Filing date	Mar 2, 2016
Priority date	Mar 25, 2015
Publication date	Jun 23, 2020
Grant date	Jun 23, 2020

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 a light 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 light emitting layer-forming composition for applying and forming a light emitting layer of an organic electroluminescent element, comprising:
at least one selected from the group consisting of a polycyclic aromatic compound represented by the following general formula (A) and a polycyclic aromatic multimer compound having a plurality of structures represented by the following general formula (A) as a first component;
at least one selected from the group consisting of compounds represented by the following general formulas (B-1) to (B-6) as a second component; and
at least one organic solvent as a third component

wherein in the above formula (A) ring A, ring B, and ring C each independently represent an aryl ring or a heteroaryl ring, at least one hydrogen atom in these rings may be substituted,
Y 1 represents B,
X 1 and X 2 each independently represent 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 alkyl, R of the N—R may be bonded to the ring A, ring B, and/or ring C with a linking group or a single bond,
at least one hydrogen atom in a compound or a structure represented by the above formula (A) may be substituted by a group represented by the following general formula (FG-1), a group represented by the following general formula (FG-2), an alkyl having 1 to 24 carbon atoms, a halogen atom, or a deuterium atom, further 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 or structure represented by the above formula (A) 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

wherein in the above formulas (B-1) to (B-4) Ar's each independently represent a hydrogen atom, 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,
adjacent groups among Ar's may be bonded to each other to form an aryl ring or a heteroaryl ring together with a mother skeleton of an anthracene ring, a pyrene ring, a fluorene ring, or a carbazole ring, 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, and
n represents an integer of 1 to a maximum substitutable number;
wherein in the above formula (B-5) R 1 to R 11 each independently represent a hydrogen atom, 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,
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, and at least one hydrogen atom in these may be further substituted by an aryl, a heteroaryl, or a diarylamino;
wherein in the above formula (B-6) monomer units (MU's) each independently represent at least one selected from the group consisting of divalent groups of compounds represented by the above general formulas (B-1) to (B-5), two hydrogen atoms in MU are substituted by an endcap unit (EC) or MU,
EC's each independently represent a hydrogen atom, an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, or an aryloxy, at least one hydrogen in these may be further substituted by an aryl, a heteroaryl, or a diarylamino, and
k is an integer of 2 to 50,000;
at least one hydrogen atom in compounds represented by the above formulas (B-1) to (B-5), a divalent group of compounds represented by the above formulas (B-1) to (B-5) in the above formula (B-6), or EC in the above formula (B-6) may be substituted by a group represented by the following general formula (FG-1), a group represented by the following general formula (FG-2), an alkyl having 1 to 24 carbon atoms, a halogen atom, or a deuterium atom,
further any —CH 2 — in the alkyl may be substituted by —O— or —Si(CH 3 ) 2 —, any —CH 2 — in the alkyl excluding —CH 2 — directly bonded to compounds represented by the above formulas (B-1) to (B-6), a divalent group of a compound represented by the above formulas (B-1) to (B-5) in the above formula (B-6), or EC in the above formula (B-6) 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;

wherein in the above 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 represents an integer of 0 to 5, and
p represents an integer of 1 to 5;

wherein in the above 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 represents an integer of 0 to 4, and
n's each independently represent an integer of 0 to 5.

2. The light emitting layer-forming composition described in claim 1 , in which the first component is at least one selected from the group consisting of a polycyclic aromatic compound represented by the following general formula (A′) and a polycyclic aromatic multimer compound having a plurality of structures represented by the following general formula (A′)

wherein in the above formula (A′) 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 bon

Assignees

• Kwansei Gakuin Educational Found
• Jnc Corp

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

• C09K2211/1096

  containing other heteroatoms · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title