Polycyclic aromatic compound

Patent metadata

Field	Value
Publication number	US-10686141-B2
Application number	US-201715696527-A
Country	US
Kind code	B2
Filing date	Sep 6, 2017
Priority date	Sep 7, 2016
Publication date	Jun 16, 2020
Grant date	Jun 16, 2020

Abstract

By providing a novel polycyclic aromatic compound in which a plurality of aromatic rings are linked via a boron atom, a nitrogen atom, or the like, options of a material for an organic EL element are increased. In addition, by using the novel polycyclic aromatic compound as a material for an organic electroluminescent element, an excellent organic EL element is provided.

First claim

The invention claimed is:

1. A polycyclic aromatic compound represented by the following general formula (1) or a dimer of a polycyclic aromatic compound, comprising two structures each represented by the following general formula (1),

in the above formula (1),
ring A, ring B, and ring C each independently represent an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted,
Y 1 represents B, P═S, P(—R) 2 , Al, Ga, Si—R, Ge—R, Sn—R, Sb═S, Sb(—R) 2 , Sb to which orthochloranil is bonded, Bi, Bi═O, Bi═S, Bi(—R) 2 , or Bi to which orthochloranil is bonded, R of the moieties P(—R) 2 , Si—R, Ge—R, Sn—R, Sb(—R) 2 , and Bi(—R) 2 represents an aryl, an alkyl, an alkoxy, an aryloxy, or a halogen atom, and two Rs among the moieties P(—R) 2 , Sb(—R) 2 and Bi(—R) 2 may be bonded to each other via a single bond or by fusing to form a ring,
X 1 , X 2 , and X 3 each independently represent O, N—R, S, or Se, R of the moiety N—R represents an aryl which may be substituted, a heteroaryl which may be substituted, an alkyl, or a cycloalkyl, at least one of X 1 , X 2 , and X 3 represents N—R, and R of the moiety N—R may be bonded to the ring A, ring B, and/or ring C via a linking group or a single bond or by fusing,
at least one hydrogen atom in the polycyclic aromatic compound or structure represented by formula (1) may be substituted by cyano, a halogen atom, or a deuterium atom, and
the polycyclic aromatic compound represented by formula (1) has at least one halogen as a substituent.

2. The polycyclic aromatic compound described in claim 1 or a dimer thereof, in which
the ring A, ring B, and ring C each independently represent an aryl ring or a heteroaryl ring,
at least one hydrogen atom in the ring A, ring B, and ring C may be substituted by a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted arylsulfonyl, a substituted or unsubstituted diarylphosphine, a substituted or unsubstituted diarylphosphine oxide, or a substituted or unsubstituted diarylphosphine sulfide,
the ring A, ring B, and ring C each have a 5-membered or a 6-membered ring sharing a bond with a fused tricyclic structure at the center of the above formula (1) constituted by Y′, X 2 , and X 3 ,
Y 1 represents B, P═S, P(—R) 2 , Al, Ga, Si—R, Ge—R, Sn—R, Sb═S, Sb(—R) 2 , Sb to which orthochloranil is bonded, Bi, Bi═O, Bi═S, Bi(—R) 2 , or Bi to which orthochloranil is bonded, R of the moieties P(—R) 2 , Si—R, Ge—R, Sn—R, Sb(—R) 2 , and Bi(—R) 2 represents an aryl, an alkyl, an alkoxy, an aryloxy, or a halogen atom, and two Rs among the moieties P(—R) 2 , Sb(—R) 2 and Bi(—R) 2 may be bonded to each other via a single bond or by fusing to form a ring,
X 1 , X 2 , and X 3 each independently represent O, N—R, S, or Se, R of the moiety N—R represents an aryl which may be substituted by an alkyl, a heteroaryl which may be substituted by an alkyl, an alkyl, or a cycloalkyl, at least one of X 1 , X 2 , and X 3 represents N—R, R of the moiety N—R may be bonded to the ring A, ring B, and/or ring C via —O—, —S—, >N—R, an arylene having 6 to 30 carbon atoms, or a single bond, or by fusing, R of the moiety —C(—R) 2 -represents a hydrogen atom, an alkyl, or an aryl, and R of the moiety>N—R represents an alkyl or an aryl which may be substituted by an alkyl,
at least one hydrogen atom in the polycyclic aromatic compound or structure represented by formula (1) may be substituted by cyano, a halogen atom, or a deuterium atom, and
the polycyclic aromatic compound represented by formula (1) has at least one halogen as a substituent.

3. The polycyclic aromatic compound described in claim 1 or a dimer thereof, wherein the general formula (1) is represented by the following general formula (2)

in the above formula (2),
R 1 to R 9 each independently represent a hydrogen atom, an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, an alkoxy, or an aryloxy, at least one hydrogen atom in these may be substituted by an aryl, a heteroaryl, or an alkyl, adjacent groups among R 1 to R 9 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, an alkyl, an alkoxy, or an aryloxy, and at least one hydrogen atom in these substituents may be substituted by an aryl, a heteroaryl, or an alkyl,
Y 1 represents B, P═S, P(—R) 2 , Al, Ga, Si—R, Ge—R, Sn—R, Sb═S, Sb(—R) 2 , Sb to which orthochloranil is bonded, Bi, Bi═O, Bi═S, Bi(—R) 2 , or Bi to which orthochloranil is bonded, R of the moieties P(—R) 2 , Si—R, Ge—R, Sn—R, Sb(—R) 2 , and Bi(—R) 2 represents an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, an alkoxy having 1 to 6 carbon atoms, an aryloxy having 6 to 12 carbon atoms, or a halogen atom, and two Rs among the moieties P(—R) 2 , Sb(—R) 2 and Bi(—R) 2 may be bonded to each other via a single bond or by fusing to form a ring,
X 1 , X 2 , and X 3 each independently represent O, N—R, S, or Se, R of the moiety N—R represents an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 6 carbon atoms, at least two of X 1 , X 2 , and X 3 represent N—R, R of the moiety N—R may be bonded to the ring a, ring b, or ring c via —O—, —S—, —C(—R) 2 —, >N—R, an arylene having 6 to 12 carbon atoms, or a single bond, or by fusing, R of the moiety —C(—R) 2 — represents an alkyl having 1 to 6 carbon atoms or an aryl having 6 to 12 carbon atoms, and R of the moiety>N—R represents an alkyl having 1 to 6 carbon atoms or an aryl having 6 to 12 carbon atoms which may be substituted by an alkyl having 1 to 6 carbon atoms,
at least one hydrogen atom in the polycyclic aromatic compound or structure represented by formula (2) may be substituted by cyano, a halogen atom, or a deuterium atom, and
the polycyclic aromatic compound represented by formula (2) has at least one halogen as a substituent.

4. The polycyclic aromatic compound described in claim 3 or a dimer thereof, in which
R 1 to R 9 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), adjacent groups among R 1 to R 9 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 the ring a, ring b, or ring c, and at least one hydrogen atom in the ring thus formed may be substituted by an aryl having 6 to 10 carbon atoms,
Y 1 represents B, P═S, Si—R, Sb═S, Sb to which orthochloranil is bonded, Bi, Bi═O, Bi═S, or Bi to which orthochloranil is bonded, R of the moiety Si—R represents an aryl having 6 to 10 carbon atoms or an alkyl having 1 to 4 carbon atoms,
X 1 , X 2 , and X 3 each independently represent O, N—R, or S, R of the moiety N—R represents an aryl having 6 to 10 carbon atoms or an alkyl having 1 to 4 carbon atoms, and at least two of X 1 , X 2 , and X 3 represent N—R,
at least one hydrogen atom in the polycyclic aromatic compound or structure represented by formula (

Assignees

• Kwansei Gakuin Educational Found
• Jnc Corp

Inventors

• Hatakeyama Takuji
• NAKATSUKA Soichiro
• Gotoh Hajime
• Sasada Yasuyuki
• Yanai Motoki
• Ikuta Toshiaki

Classifications

• H10K85/658

  Organoboranes · CPC title

• H10K85/657

  Polycyclic condensed heteroaromatic hydrocarbons · CPC title

• C07F5/02 Primary

  Boron compounds · CPC title

• H10K50/15

  Hole transporting layers · CPC title

• H10K50/16

  Electron transporting layers · CPC title