Phenyl-substituted 1,3.5-triazine compound, process for producing the same, and organic electroluminescent device containing the same as component

A process for producing a phenyl-substituted 1,3,5-triazine compound represented by the following general formula (1a):

• wherein Ar1, Ar2, R1, R2, R3, X1, p and Ar3 are the same as defined below with regard to the general formulae (2a) and (3),
• characterized by coupling a compound represented by the following general formula (2a) with a compound represented by the following general formula (3) in the presence of a metal catalyst;
• M-X1p—Ar3 (2a)
• wherein
• X1 represents a phenylene group, a naphthylene group or a pyridylene group, wherein these groups may have at least one substituent 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 X1s may be the same or different;
• Ar3 represents a pyridyl group which may have at least one substituent selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom, or a phenyl group which may have at least one substituent selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom;
• and
• M represents a —ZnR4 group, a —MgR5 group, a —SnR6R7R8 group, a —B(OH)2 group, a —BR9 group, a —BF3−(Z1)+ group or a —SiR10R11R12 group, wherein R4 and R5 represent a chlorine atom, a bromine atom or an iodine atom;
• R6, R7 and R8 each independently represent an alkyl group having 1 to 4 carbon atoms;
• R9 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;
• (Z1)+ represents an alkali metal ion or a quaternary ammonium ion;
• and R10, R11 and R12 each independently represent a methyl group, an ethyl group, a methoxy group, an ethoxy group or a chlorine atom;
• Wherein
• Ar1 and Ar2 each independently represent a phenyl group, a naphthyl group or a biphenylyl group, wherein these groups may have at least one substituent selected from an alkyl group having 1 to 6 carbon atoms and a trifluoromethyl group;
• R1, R2 and R3 each independently represent a hydrogen atom or a methyl group;
• and
• Y1 and Y2 each independently represent a chorine atom, a bromine atom, an iodine atom or a trifluoromethylsulfonyloxy group.

A process for producing a phenyl-substituted 1,3,5-triazine compound represented by the following general formula (1):

• wherein Ar1, Ar2, R1, R2, R3, X1, X2, p, q, Ar3 and Ar4 are the same as defined below with regard to the general formulae (2a), (3) and (2b),
• characterized by coupling a compound represented by the following general formula (2a) with a compound represented by the following general formula (3) in the presence of a metal catalyst to give a compound represented by the following general formula (4);
• and then, coupling the compound of formula (4) with a compound represented by the following general formula (2b) in the presence of a metal catalyst;
• M-X1p—Ar3 (2a)
• wherein
• X1 represents a phenylene group, a naphthylene group or a pyridylene group, wherein these groups may have at least one substituent 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 X1s may be the same or different;
• Ar3 represents a pyridyl group which may have at least one substituent selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom, or a phenyl group which may have at least one substituent selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom;
• and
• M represents a —ZnR4 group, a —MgR5 group, a —SnR6R7R8 group, a —B(OH)2 group, a —BR9 group, a —BF3−(Z1)+ group or a —SiR10R11 R12 group, wherein R4 and R5 represent a chlorine atom, a bromine atom or an iodine atom;
• R6, R7 and R8 each independently represent an alkyl group having 1 to 4 carbon atoms;
• R9 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;
• (Z1)+ represents an alkali metal ion or a quaternary ammonium ion;
• and R10, R11 and R12 each independently represent a methyl group, an ethyl group, a methoxy group, an ethoxy group or a chlorine atom;
• wherein
• Ar1 and Ar2 each independently represent a phenyl group, a naphthyl group or a biphenylyl group, wherein these groups may have at least one substituent selected from an alkyl group having 1 to 6 carbon atoms and a trifluoromethyl group;
• R1, R2 and R3 each independently represent a hydrogen atom or a methyl group;
• and
• Y1 and Y2 each independently represent a chorine atom, a bromine atom, an iodine atom or a trifluoromethylsulfonyloxy group;
• group or a chlorine atom;
• wherein Ar1, Ar2, R1, R2, R3, X1, p, Ar3 and Y2 are defined above with regard to the formulae (2a) and (3);
• M-X2q—Ar4 (2b)
• wherein
• X2 represents a phenylene group, a naphthylene group or pyridylene group, wherein these groups may have at least one substituent 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 X2s may be the same or different;
• Ar4 represents a pyridyl group which may have at least one substituent selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom, or a phenyl group which may have at least one substituent selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom;
• and M is defined above with regard to the formula (2a).

A process for producing a phenyl-substituted 1,3,5-triazine compound represented by the following general formula (1):

• wherein Ar1, Ar2, R1, R2, R3, X1, X2, p, q, Ar3 and Ar4 are the same as defined below with regard to the general formulae (2b) and (4),
• 5characterized by coupling a compound represented by the following general formula (2b) with a compound represented by the following general formula (4) in the presence of a metal catalyst;
• M-X2q—Ar4 (2b)
• wherein
• X2 represents a phenylene group, a naphthylene group or a pyridylene group, wherein these groups may have at least one substituent 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 X2s may be the same or different;
• Ar4 represents a pyridyl group which may have at least one substituent selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom, or a phenyl group which may have at least one substituent selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom;
• and
• M represents a —ZnR4 group, a —MgR5 group, a —SnR6R7R8 group, a —B(OH)2 group, a —BR9 group, a —BF3−(Z1)+ group or a —SiR10R11R12 group, wherein R4 and R5 represent a chlorine atom, a bromine atom or an iodine atom;
• R6, R7 and R8 each independently represent an alkyl group having 1 to 4 carbon atoms;
• R9 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;
• (Z1)+ represents an alkali metal ion or a quaternary ammonium ion;
• and R10, R11 and R12 each independently represent a methyl group, an ethyl group, a methoxy group, an ethoxy group or a chlorine atom;
• wherein
• Ar1 and Ar2 each independently represent a phenyl group, a naphthyl group or a biphenylyl group, wherein these groups may have at least one substituent selected from an alkyl group having 1 to 6 carbon atoms and a trifluoromethyl group;
• R1, R2 and R3 each independently represent a hydrogen atom or a methyl group;
• and
• X1 represents a phenylene group, a naphthylene group or a pyridylene group, wherein these groups may have at least one substituent 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 X1s may be the same or different;
• and
• Ar3 represents a pyridyl group which may have at least one substituent selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom, or a phenyl group which may have at least one substituent selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom;
• and
• Y2 represents a chorine atom, a bromine atom, an iodine atom or a trifluoromethylsulfonyloxy group.

A compound characterized by being represented by the following general formula (4):

• wherein:
• Ar1 and Ar2 each independently represent a phenyl group, a naphthyl group or a biphenylyl group, wherein these groups may have at least one substituent selected from an alkyl group having 1 to 6 carbon atoms and a trifluoromethyl group;
• R1, R2 and R3 each independently represent a hydrogen atom or a methyl group;
• X1 represents a phenylene group, a naphthylene group or a pyridylene group, wherein these groups may have at least one substituent 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 X1s may be the same or different;
• and
• Ar3 represents a pyridyl group which may have at least one substituent selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom, or a phenyl group which may have at least one substituent selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom.

A process for producing a compound represented by the following formula (4):

• wherein Ar1, Ar2, R1, R2, R3, X1, p, Ar3 and Y2 are the same as defined below with regard to the general formulae (2a) and (3),
• characterized by coupling a compound represented by the following general formula (2a) with a compound represented by the following general formula (3) in the presence of a metal catalyst;
• M-X1p—Ar3 (2a)
• wherein
• X1 represents a phenylene group, a naphthylene group or a pyridylene group, wherein these groups may have at least one substituent 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 X1s may be the same or different;
• Ar3 represents a pyridyl group which may have at least one substituent selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom, or a phenyl group which may have at least one substituent selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom;
• and
• M represents a —ZnR4 group, a —MgR5 group, a —SnR6R7R8 group, a —B(OH)2 group, a —BR9 group, a —BF3−(Z1)+ group or a —SiR10R11 R12 group, wherein R4 and R5 represent a chlorine atom, a bromine atom or an iodine atom;
• R6, R7 and R8 each independently represent an alkyl group having 1 to 4 carbon atoms;
• R9 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;
• (Z1)+ represents an alkali metal ion or a quaternary ammonium ion;
• and R10, R11 and R12 each independently represent a methyl group, an ethyl group, a methoxy group, an ethoxy group or a chlorine atom;
• wherein
• Ar1 and Ar2 each independently represent a phenyl group, a naphthyl group or a biphenylyl group, wherein these groups may have at least one substituent selected from an alkyl group having 1 to 6 carbon atoms and a trifluoromethyl group;
• R1, R2 and R3 each independently represent a hydrogen atom or a methyl group;
• and
• Y1 and Y2 each independently represent a chorine atom, a bromine atom, an iodine atom or a trifluoromethylsulfonyloxy group.

An organic electroluminescent device characterized by containing as a component a phenyl-substituted 1,3,5-triazine compound represented by the following general formula (1):

• wherein:
• Ar1 and Ar2 each independently represent a phenyl group, a naphthyl group or a biphenylyl group, wherein these groups may have at least one substituent selected from an alkyl group having 1 to 6 carbon atoms and a trifluoromethyl group;
• R1, R2 and R3 each independently represent a hydrogen atom or a methyl group;
• X1 and X2 each independently represent a phenylene group, a naphthylene group or a pyridylene group, wherein these groups may have at least one substituent 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 X1s may be the same or different, and when q is 2, the adjacent X2s may be the same or different;
• and
• Ar3 and Ar4 each independently represent a pyridyl group which may have at least one substituent selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom, or a phenyl group which may have at least one substituent selected from an alkyl group having 1 to 4 carbon atoms and a fluorine atom.