IP Library Granted Patent US 11,136,341
Granted Patent B2
US 11,136,341 · App. 16/803,392 · Granted Oct 5, 2021

Polycyclic aromatic compound and light emission layer-forming composition

Inventors: Takuji Hatakeyama (Hyogo, JP); Yasuhiro Kondo (Chiba, JP); Keiichi Nakamoto (Chiba, JP); Motoki Yanai (Chiba, JP)
Assignees: Kwansei Gakuin Educational Foundation; SK Materials JNC Co., Ltd.
C07F5/02C07F5/027C09K11/06H01L51/008H01L51/0052H01L51/0058H01L51/0059H01L51/0071H01L51/0072H01L51/50C09K2211/1096H01L51/5012
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Quick Facts
Patent No.
US 11,136,341
App. No.
16/803,392
Granted
Oct 5, 2021
Kind
B2
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.

Claims (39)

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 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.

9. The polycyclic aromatic compound or the multimer thereof according to claim 8 , wherein the compound represented by the above formula (A′) or the multimer thereof is a compound represented by the above formula (1-422-z), (1-1152-z), or (1-2679-z).

10. 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.

11. The polycyclic aromatic compound or the multimer thereof according to claim 1 , wherein at least one hydrogen atom in a compound or a structure represented by the above formula IA′) is substituted by a group represented by the above formula (FG-1).

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 26, 2021
From: JNC CORPORATION
To: SK MATERIALS JNC CO., LTD.
Reel/Frame 056038/0288 →
Priority Claims (1)
JP 2015-061841 · Mar 25, 2015 · national
Continuity (2)
Division 15559912
Related Publication 20200190116A1 · Jun 18, 2020