Phenyl-substituted 1,3,5-triazine compound, process for producing the same, and organic electroluminescent device containing the same as component

1. A phenyl-substituted 1,3,5-triazine compound of formula (1):

wherein:

Ar 1 and Ar 2 each independently represent a phenyl group, a naphthyl group or a biphenylyl group, wherein these groups may have one or more substituents selected from an alkyl group having 1 to 6 carbon atoms and a trifluoromethyl group;

R 1 , R 2 and R 3 each independently represent a hydrogen atom or a methyl group;

X 1 and X 2 each independently represent a phenylene group, a naphthylene group or a pyridylene group, wherein these groups may have one or more substituents selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom;

p and q each independently represent an integer in the range of 0 to 2, wherein, when p is 2, the adjacent X 1 s may be the same or different, and when q is 2, the adjacent X 2 s may be the same or different; and

Ar 3 and Ar 4 each independently represent a pyridyl group which may have one or more substituents selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom, or a phenyl group which may have one or more substituents selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom.

2. The phenyl-substituted 1,3,5-triazine compound according to claim 1 , wherein either one or both of Ar 3 and Ar 4 represent a pyridyl group which may have one or more substituents selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom.

3. A process for producing a phenyl-substituted 1,3,5-triazine compound of formula (1a):

wherein Ar 1 , Ar 2 , R 1 , R 2 , R 3 , X 1 , p and Ar 3 are the same as defined below with regard to formulae (2a) and (3),

comprising coupling a compound of formula (2a) with a compound of formula (3) in the presence of a metal catalyst;

M-X 1 p —Ar 3   (2a)

wherein

X 1 represents a phenylene group, a naphthylene group or a pyridylene group, wherein these groups may have one or more substituents selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom;

p represents an integer in the range of 0 to 2, wherein, when p is 2, the adjacent X 1 s may be the same or different;

Ar 3 represents a pyridyl group which may have one or more substituents selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom, or a phenyl group which may have one or more substituents selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom; and

M represents a —ZnR 4 group, a —MgR 5 group, a —SnR 6 R 7 R 8 group, a —B(OH) 2 group, a —BR 9 group, a —BF 3 − (Z 1 ) + group or a —SiR 10 R 11 R 12 group, wherein R 4 and R 5 represent a chlorine atom, a bromine atom or an iodine atom; R 6 , R 7 and R 8 each independently represent an alkyl group having 1 to 4 carbon atoms; R 9 represents a methoxy group, an isopropoxy group, a 2,3-dimethylbutane-2,3-dioxy group, an ethylenedioxy group, a 1,3-propanedioxy group or 1,2-phenylenedioxy group; (Z 1 ) + represents an alkali metal ion or a quaternary ammonium ion; and R 10 , R 11 and R 12 each independently represent a methyl group, an ethyl group, a methoxy group, an ethoxy group or a chlorine atom;

wherein

Ar 1 and Ar e each independently represent a phenyl group, a naphthyl group or a biphenylyl group, wherein these groups may have one or more substituents selected from an alkyl group having 1 to 6 carbon atoms and a trifluoromethyl group;

R 1 , R 2 and R 3 each independently represent a hydrogen atom or a methyl group; and

Y 1 and Y 2 each independently represent a chorine atom, a bromine atom, an iodine atom or a trifluoromethylsulfonyloxy group.

4. The production process according to claim 3 , wherein Ar 3 represents a pyridyl group which may have one or more substituents selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom.

5. A process for producing a phenyl-substituted 1,3,5-triazine compound of formula (1):

wherein Ar 1 , Ar 2 , R 1 , R 2 , R 3 , X 1 , X 2 , p, q, Ar 3 and Ar 4 are the same as defined below with regard to formulae (2a), (3) and (2b),

comprising coupling a compound of formula (2a) with a compound of formula (3) in the presence of a metal catalyst to give a compound of formula (4); and then, coupling the compound of formula (4) with a compound of formula (2b) in the presence of a metal catalyst;

M-X 1 p —Ar 3   (2a)

wherein

X 1 represents a phenylene group, a naphthylene group or a pyridylene group, wherein these groups may have one or more substituents selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom;

p represents an integer in the range of 0 to 2, wherein, when p is 2, the adjacent X 1 s may be the same or different;

Ar 3 represents a pyridyl group which may have one or more substituents selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom, or a phenyl group which may have one or more substituents selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom; and

M represents a —ZnR 4 group, a —MgR 5 group, a —SnR 6 R 7 R 8 group, a —B(OH) 2 group, a —BR 9 group, a —BF 3 − (Z 1 ) + group or a —SiR 10 R 11 R 12 group, wherein R 4 and R 5 represent a chlorine atom, a bromine atom or an iodine atom; R 6 , R 7 and R 8 each independently represent an alkyl group having 1 to 4 carbon atoms; R 9 represents a methoxy group, an isopropoxy group, a 2,3-dimethylbutane-2,3-dioxy group, an ethylenedioxy group, a 1,3-propanedioxy group or a 1,2-phenylenedioxy group; (Z 1 ) + represents an alkali metal ion or a quaternary ammonium ion; and R 10 , R 11 and R 12 each independently represent a methyl group, an ethyl group, a methoxy group, an ethoxy group or a chlorine atom;

wherein

Ar 1 and Ar 2 each independently represent a phenyl group, a naphthyl group or a biphenylyl group, wherein these groups may have one or more substituents selected from an alkyl group having 1 to 6 carbon atoms and a trifluoromethyl group;

R 1 , R 2 and R 3 each independently represent a hydrogen atom or a methyl group; and

Y 1 and Y 2 each independently represent a chorine atom, a bromine atom, an iodine atom or a trifluoromethylsulfonyloxy group;

wherein Ar 1 , Ar 2 , R 1 , R 2 , R 3 , X 1 , p, Ar 3 and Y 2 are defined above with regard to the formulae (2a) and (3);

M-X 2 q —Ar 4   (2b)

wherein

X 2 represents a phenylene group, a naphthylene group or pyridylene group, wherein these groups may have one or more substituents selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom;

q represents an integer in the range of 0 to 2, wherein, when q is 2, the adjacent X 2 s may be the same or different;

Ar 4 represents a pyridyl group which may have one or more substituents selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom, or a phenyl group which may have one or more substituents selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom; and

M is defined above with regard to formula (2a).

6. The production process according to claim 5 , wherein either one or both of Ar 3 and Ar 4 represents a pyridyl group which may have one or more substituents selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom.

7. A process for producing a phenyl-substituted 1,3,5-triazine compound of formula (1):

wherein Ar 1 , Ar 2 , R 1 , R 2 , R 3 , X 1 , X 2 , p, q, Ar 3 and Ar 4 are the same as defined below with regard to formulae (2b) and (4),

comprising coupling a compound of formula (2b) with a compound of formula (4) in the presence of a metal catalyst;

M-X 2 q —Ar 4   (2b)

wherein

X 2 represents a phenylene group, a naphthylene group or a pyridylene group, wherein these groups may have one or more substituents selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom;

q represents an integer in the range of 0 to 2, wherein, when q is 2, the adjacent X 2 s may be the same or different;

Ar 4 represents a pyridyl group which may have one or more substituents selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom, or a phenyl group which may have one or more substituents selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom; and

M represents a —ZnR 4 group, a —MgR 5 group, a —SnR 6 R 7 R 8 group, a —B(OH) 2 group, a —BR 9 group, a —BF 3 − (Z 1 ) + group or a —SiR 10 R 11 R 12 group, wherein R 4 and R 5 represent a chlorine atom, a bromine atom or an iodine atom; R 6 , R 7 and R 8 each independently represent an alkyl group having 1 to 4 carbon atoms; R 9 represents a methoxy group, an isopropoxy group, a 2,3-dimethylbutane-2,3-dioxy group, an ethylenedioxy group, a 1,3-propanedioxy group or a 1,2-phenylenedioxy group; (Z 1 ) + represents an alkali metal ion or a quaternary ammonium ion; and R 10 , R 11 and R 12 each independently represent a methyl group, an ethyl group, a methoxy group, an ethoxy group or a chlorine atom;

wherein

Ar 1 and Ar 2 each independently represent a phenyl group, a naphthyl group or a biphenylyl group, wherein these groups may have one or more substituents selected from an alkyl group having 1 to 6 carbon atoms and a trifluoromethyl group;

R 1 , R 2 and R 3 each independently represent a hydrogen atom or a methyl group; and

X 1 represents a phenylene group, a naphthylene group or a pyridylene group, wherein these groups may have one or more substituents selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom;

p represents an integer in the range of 0 to 2, wherein, when p is 2, the adjacent X 1 s may be the same or different; and

Ar 3 represents a pyridyl group which may have one or more substituents selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom, or a phenyl group which may have one or more substituents selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom; and

Y 2 represents a chorine atom, a bromine atom, an iodine atom or a trifluoromethylsulfonyloxy group.

8. The production process according to claim 7 , wherein either one or both of Ar 3 and Ar 4 represents a pyridyl group which may have one or more substituents selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom.

9. The production process according to claim 3 , wherein the metal catalyst is a palladium catalyst, a nickel catalyst or an iron catalyst.

10. The production process according to claim 3 , wherein the metal catalyst is a palladium catalyst.

11. The production process according to claim 5 , wherein the metal catalyst is a palladium catalyst, a nickel catalyst or an iron catalyst.

12. The production process according to claim 7 , wherein the metal catalyst is a palladium catalyst, a nickel catalyst or an iron catalyst.