Cyclic azine compound having adamantyl group, production method, and organic electroluminescent device containing it as constituent component

Patent metadata

Field	Value
Publication number	US-9812652-B2
Application number	US-201414902179-A
Country	US
Kind code	B2
Filing date	Jul 8, 2014
Priority date	Jul 9, 2013
Publication date	Nov 7, 2017
Grant date	Nov 7, 2017

Abstract

An azine compound represented by the formula (1), a method for its production and an organic electroluminescent device containing it as a constituent component.

wherein Ad each independently represents a 1-adamantyl group, etc., p and q are each independently 0 or 1, Ar 1 and Ar 2 are each independently a single bond (but only when p is 1, or q is 1), or a pyridyl group which may be substituted by a phenyl group, etc., incidentally, Ad groups on Ar 1 and Ar 2 are each independently bonded to said pyridyl group, etc., Ar 2 is each independently a C 3-13 heteroaromatic group which may be substituted by a fluorine atom, etc., X 1 , X 2 , X 3 and X 4 are each independently a single bond, etc., m and n are each independently 0, 1 or 2, Z is a nitrogen atom, etc., n+p+q is 1, 2 or 3.

First claim

The invention claimed is:

1. A cyclic azine compound represented by the formula (1):

wherein Ad each independently represents a 1-adamantyl group (Ad 1 ) or a 2-adamantyl group (Ad 2 ):

p and q are each independently 0 or 1,
Ar 1 and Ar a are each independently a single bond but only when p is 1 or q is 1, a C 6-30 aromatic hydrocarbon group, which may have, as a substituent, a fluorine atom, a C 1-4 alkyl group, a C 6-18 aromatic hydrocarbon group, a C 6-18 aromatic hydrocarbon group substituted by a fluorine atom, a C 6-18 aromatic hydrocarbon group substituted by a C 1-4 alkyl group, a C 6-18 aromatic hydrocarbon group substituted by a C 3-13 heteroaromatic group, a C 3-13 heteroaromatic group, or a C 3-13 heteroaromatic group substituted by a C 1-4 alkyl group, or a pyridyl group which may be substituted by a phenyl group or a methyl group,
Ad groups on Ar 1 and Ar 3 are each independently bonded to said C 6-30 aromatic hydrocarbon group or said pyridyl group,
Ar 2 is each independently a C 3-13 heteroaromatic group or a C 6-18 aromatic hydrocarbon group, wherein these groups each independently may have, as a substituent, a fluorine atom, a C 1-4 alkyl group, a C 6-18 aromatic hydrocarbon group, a C 6-18 aromatic hydrocarbon group substituted by a fluorine atom, a C 6-18 aromatic hydrocarbon group substituted by a C 1-4 alkyl group, a C 6-18 aromatic hydrocarbon group substituted by a C 3-13 heteroaromatic group, a C 3-13 heteroaromatic group, or a C 3-13 heteroaromatic group substituted by a C 1-4 alkyl group,
X 1 , X 2 , X 3 and X 4 are each independently a single bond or a C 4-14 arylene group, which may be substituted by a fluorine atom, a C 1-4 alkyl group, a phenyl group, a biphenyl group or a naphthyl group,
m is 0, 1 or 2,
n is 0, 1 or 2,
Z is a nitrogen atom, and
n+p+q is 1, 2 or 3.

2. The cyclic azine compound according to claim 1 , wherein Ar 1 and Ar 3 are each independently a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, an anthryl group, a pyrenyl group, a triphenylenyl group, a chrysenyl group, a fluoranthenyl group, an acenaphthylenyl group, a pyridyl group, a pyrazyl group, a pyrimidyl group, a pyridazyl group, a triazyl group, a quinolyl group or an isoquinolyl group, wherein these groups each independently may have, as a substituent, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group or a t-butyl group.

3. The cyclic azine compound according to claim 1 , wherein Ar 2 is a pyridyl group, a pyrazyl group, a pyridazyl group, a pyrimidyl group, a triazyl group, a quinolyl group, an isoquinolyl group, a naphthyridyl group, a quinazolyl group, a quinoxalyl group, a benzoquinolyl group, an acridyl group, a phenanthridyl group, a phenanthrolyl group, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, an anthryl group, a pyrenyl group, a triphenylenyl group, a chrysenyl group, a fluoranthenyl group or an acenaphthylenyl group, wherein these groups each independently may have, as a substituent, a methyl group, a phenyl group, a naphthyl group, a phenanthryl group, an anthryl group, a pyrenyl group, a triphenylenyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, a quinolyl group or an isoquinolyl group.

4. The cyclic azine compound according to claim 1 , wherein X 1 , X 2 , X 3 and X 4 are, each independently, a phenylene group, a naphthylene group, a pyridylene group, a pyrazylene group, a pyrimidylene group, wherein these groups may be substituted by a fluorine atom, a methyl group or a phenyl group, or a single bond.

5. The cyclic azine compound according to claim 1 , wherein Ad is a 1-adamantyl group.

6. The cyclic azine compound according to claim 1 , wherein m is 1.

7. The cyclic azine compound according to claim 1 , wherein n is 1.

8. A method for producing a cyclic azine compound represented by the formula (1) as defined in claim 1 , which comprises sequentially or simultaneously subjecting a compound represented by the formula (2), and compounds represented by the formulae (3) and (4), to a coupling reaction in the presence or absence of a base and in the presence of a palladium catalyst,

wherein Ad, p, q, Ar 1 , Ar 2 , Ar 3 , X 1 , X 2 , X 3 , X 4 , m, n and Z are as defined in claim 1 , and
n+p+q is 1, 2 or 3,
Y 1 and Y 2 each independently represents a leaving group,
M 1 and M 2 each independently represents a ZnR 1 , MgR 2 , Sn(R 3 ) 3 or B(OR 4 ) 2 , wherein
R 1 and R 2 are each independently a chlorine atom, a bromine atom or an iodine atom, R 3 is a C 1-4 alkyl group or a phenyl group, R 4 is a hydrogen atom, a C 1-4 alkyl group or a phenyl group, two R 4 in B(OR 4 ) 2 may be the same or different, or the two R 4 may together form a ring containing an oxygen atom and a boron atom.

9. A method for producing a cyclic azine compound represented by the formula (1) as defined in claim 1 , which comprises subjecting a compound represented by the formula (5) and a compound represented by the formula (6), to a coupling reaction in the presence or absence of a base and in the presence of a palladium catalyst,

wherein Ad, p, q, Ar 1 , Ar 2 , Ar 3 , X 1 , X 2 , X 3 , X 4 , m, n and Z are as defined in claim 1 , and
n+p+q is 1, 2 or 3,
Y 3 represents a leaving group,
M 3 represents a ZnR 1 , MgR 2 , Sn(R 3 ) 3 or B(OR 4 ) 2 , wherein R 1 and R 2 are each independently a chlorine atom, a bromine atom or an iodine atom, R 3 is a C 1-4 alkyl group or a phenyl group, R 4 is a hydrogen atom, a C 1-4 alkyl group or a phenyl group, two R 4 in B(OR 4 ) 2 may be the same or different, or the two R 4 may together form a ring containing an oxygen atom and a boron atom.

10. A method for producing a cyclic azine compound represented by the formula (1) as defined in claim 1 , which comprises subjecting a compound represented by the formula (7) and a compound represented by the formula (8), to a coupling reaction in the presence or absence of a base and in the presence of a palladium catalyst,

wherein Ad, p, q, Ar 1 , Ar 2 , Ar 3 , X 1 , X 2 , X 3 , X 4 , m, n and Z are as defined in claim 1 , and
n+p+q is 1, 2 or 3,
Y 4 represents a leaving group,
M 4 represents a ZnR 1 , MgR 2 , Sn(R 3 ) 3 or B(OR 4 ) 2 , wherein R 1 and R 2 are each independently a chlorine atom, a bromine atom or an iodine atom, R 3 is a C 1-4 alkyl group or a phenyl group, R 4 is a hydrogen atom, a C 1-4 alkyl group or a phenyl group, two R 4 in B(OR 4 ) 2 may be the same or different, or the two R 4 may together form a ring containing an oxygen atom and a boron atom.

11. The method according to claim 8 , wherein the palladium catalyst is a palladium catalyst having a tertiary phosphine as a ligand.

12. The method according to claim 11 , wherein the palladium catalyst is a palladium catalyst having triphenylphosphine or 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl as a ligand.

13. A met

Assignees

• Tosoh Corp

Inventors

• Arai Nobumichi
• Nomura Keisuke
• Tanaka Tsuyoshi

Classifications

• C07D403/10

  linked by a carbon chain containing aromatic rings · CPC title

• H01L51/0058

  Electricity · mapped topic

• C07C2603/74

  Adamantanes · CPC title

• C07F5/025

  Boronic and borinic acid compounds · CPC title

• C09K2211/1011

  Condensed systems · CPC title