Polycyclic aromatic compound and light emission layer-forming composition

Patent metadata

Field	Value
Publication number	US-11136341-B2
Application number	US-202016803392-A
Country	US
Kind code	B2
Filing date	Feb 27, 2020
Priority date	Mar 25, 2015
Publication date	Oct 5, 2021
Grant date	Oct 5, 2021

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, Y1 is B, and X1 and X2 each independently represent O or N—R wherein at least one of X1 and X2 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 in the general formula (A′),
each of R 1 to R 11 independently represents 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,
Y 1 represents B,
each of X 1 and X 2 independently represents 0 or N-R, while at least one of X 1 and X 2 represents N-R, R of the N-R is an aryl or an alkyl, R in the N-R may be bonded to ring b and/or ring c with —O—, —S—, —C(—R) 2 -, or a single bond, R in the —C(—R) 2 —represents an alkyl having 1 to 24 carbon atoms,
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 general formula (FG-1), a group represented by the general formula (FG-2), or an alkyl having 7 to 24 carbon atoms, 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 general formula (FG-1) is as follows:

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; and wherein the general formula (FG-2) is as follows:

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 R 1 to R 11 independently represents 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),
Y 1 represents B,
each of X 1 and X 2 independently represents 0 or N-R, while at least one of X 1 and X 2 represents N-R, R of the N-R is an aryl having 6 to 18 carbon atoms or an alkyl having 1 to 12 carbon atoms,
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 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 0, and X 2 represents N-R.

7. The polycyclic aromatic compound or the multimer thereof according to claim 1 , wherein
in the above formula (A′), each of R 1 to R 11 independently represents 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′) at *

8. The polycyclic aromatic compound or the multimer thereof according to claim 1 , wherein
the compound represented by the above formula (A′) or the multimer thereof is a compound represented by the following formula (1-401-z), (1-411-z), (1-422-z), (1-447-z), (1-1152-z), (1-1159-z), (1-1201-z), (1-1210-z), (1-2623-z), or (1-2679-z)

wherein each of z's in the above formulas represents a hydrogen atom, a group repres

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

• C09K2211/1096

  containing other heteroatoms · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title