Perylene derivative synthesis process, perylene derivative and organic EL device

A perylene derivative synthesizing process comprising subjecting a fluoranthene derivative of the following formula (14):

• wherein X is Cl, Br or I, Z is a boronic acid derivative, and R1 to R6, R21 and R22 are each are a hydrogen atom, a straight, branched or cyclic alkyl radical which may be substituted, a straight, branched or cyclic alkoxy radical which may be substituted, a straight, branched or cyclic alkylthio radical which may be substituted, a straight, branched or cyclic alkenyl radical which may be substituted, a straight, branched or cyclic alkenyloxy radical which may be substituted, a straight, branched or cyclic alkenylthio radical which may be substituted, a substituted or unsubstituted aralkyl radical, a substituted or unsubstituted aralkyloxy radical, a substituted or unsubstituted aralkylthio radical, a substituted or unsubstituted aryl radical, a substituted or unsubstituted aryloxy radical, a substituted or unsubstituted arylthio radical, a substituted or unsubstituted amino radical, a cyano radical, a hydroxyl radical, a —COOM1 radical (wherein M1 is a hydrogen atom, a straight, branched or cyclic alkyl radical which may be substituted, a straight, branched or cyclic alkenyl radical which may be substituted, a substituted or unsubstituted aralkyl radical, or a substituted or unsubstituted aryl radical), a —COM2 radical (wherein M2 is a hydrogen atom, a straight, branched or cyclic alkyl radical which may be substituted, a straight, branched or cyclic alkenyl radical which may be substituted, a substituted or unsubstituted aralkyl radical, a substituted or unsubstituted aryl radical, or an amino radical), or a —OCOM3 radical (wherein M3 is a straight, branched or cyclic alkyl radical which may be substituted, a straight, branched or cyclic alkenyl radical which may be substituted, a substituted or unsubstituted aralkyl radical, or a substituted or unsubstituted aryl radical), and at least two adjoining radicals selected from among R1 to R6, R21 and R22 may bond or fuse together to form a substituted or unsubstituted carbocyclic aliphatic ring, aromatic ring or fused aromatic ring with the carbon atoms on which they substitute, to a Suzuki coupling reaction, thereby synthesizing a perylene derivative.

A perylene derivative synthesizing process comprising subjecting a benzofluoranthene derivative of the following formula (15):

• wherein X is Cl, Br or I, Z is a boronic acid derivative, and R1 to R8, R31 and R32 are each are a hydrogen atom, a straight, branched or cyclic alkyl radical which may be substituted, a straight, branched or cyclic alkoxy radical which may be substituted, a straight, branched or cyclic alkylthio radical which may be substituted, a straight, branched or cyclic alkenyl radical which may be substituted, a straight, branched or cyclic alkenyloxy radical which may be substituted, a straight, branched or cyclic alkenylthio radical which may be substituted, a substituted or unsubstituted aralkyl radical, a substituted or unsubstituted aralkyloxy radical, a substituted or unsubstituted aralkylthio radical, a substituted or unsubstituted aryl radical, a substituted or unsubstituted aryloxy radical, a substituted or unsubstituted arylthio radical, a substituted or unsubstituted amino radical, a cyano radical, a hydroxyl radical, a —COOM1 radical (wherein M1 is a hydrogen atom, a straight, branched or cyclic alkyl radical which may be substituted, a straight, branched or cyclic alkenyl radical which may be substituted, a substituted or unsubstituted aralkyl radical, or a substituted or unsubstituted aryl radical), a —COM2 radical (wherein M2 is a hydrogen atom, a straight, branched or cyclic alkyl radical which may be substituted, a straight, branched or cyclic alkenyl radical which may be substituted, a substituted or unsubstituted aralkyl radical, a substituted or unsubstituted aryl radical, or an amino radical), or a —OCOM3 radical (wherein M3 is a straight, branched or cyclic alkyl radical which may be substituted, a straight, branched or cyclic alkenyl radical which may be substituted, a substituted or unsubstituted aralkyl radical, or a substituted or unsubstituted aryl radical), and at least two adjoining radicals selected from among R1 to R8, R31 and R32 may bond or fuse together to form a substituted or unsubstituted carbocyclic aliphatic ring, aromatic ring or fused aromatic ring with the carbon atoms on which they substitute, to a Suzuki coupling reaction, thereby synthesizing a perylene derivative.

A perylene derivative synthesizing process comprising subjecting at least one derivative selected from the group consisting of 1,8-dihalogenated naphthalene derivatives of the following formula (1), 3,4-dihalogenated fluoranthene derivatives of the following formula (3), and 3,4-dihalogenated benzofluoranthene derivatives of the following formula (5) to a coupling reaction to thereby form an asymmetric compound:

• wherein X is Cl, Br or I, R1 to R4, R11 and R12 each are a hydrogen atom, a straight, branched or cyclic alkyl radical which may be substituted, a straight, branched or cyclic alkoxy radical which may be substituted, a straight, branched or cyclic alkylthio radical which may be substituted, a straight, branched or cyclic alkenyl radical which may be substituted, a straight, branched or cyclic alkenyloxy radical which may be substituted, a straight, branched or cyclic alkenylthio radical which may be substituted, a substituted or unsubstituted aralkyl radical, a substituted or unsubstituted aralkyloxy radical, a substituted or unsubstituted aralkylthio radical, a substituted or unsubstituted aryl radical, a substituted or unsubstituted aryloxy radical, a substituted or unsubstituted arylthio radical, a substituted or unsubstituted amino radical, a cyano radical, a hydroxyl radical, a —COOM1 radical (wherein M1 is a hydrogen atom, a straight, branched or cyclic alkyl radical which may be substituted, a straight, branched or cyclic alkenyl radical which may be substituted, a substituted or unsubstituted aralkyl radical, or a substituted or unsubstituted aryl radical), a —COM2 radical (wherein M2 is a hydrogen atom, a straight, branched or cyclic alkyl radical which may be substituted, a straight, branched or cyclic alkenyl radical which may be substituted, a substituted or unsubstituted aralkyl radical, a substituted or unsubstituted aryl radical, or an amino radical), or a —OCOM3 radical (wherein M3 is a straight, branched or cyclic alkyl radical which may be substituted, a straight, branched or cyclic alkenyl radical which may be substituted, a substituted or unsubstituted aralkyl radical, or a substituted or unsubstituted aryl radical), and at least two adjoining radicals selected from among R1 to R4, R11 and R12 may bond or fuse together to form a substituted or unsubstituted carbocyclic aliphatic ring, aromatic ring or fused aromatic ring with the carbon atoms on which they substitute, with the proviso that when the carbocyclic aliphatic ring, aromatic ring or fused aromatic ring has substituent radicals, the substituent radicals are the same as R1 to R4, R11 and R12,
• wherein X is Cl, Br or I, R1 to R6, R21 and R22 each are a hydrogen atom, a straight, branched or cyclic alkyl radical which may be substituted, a straight, branched or cyclic alkoxy radical which may be substituted, a straight, branched or cyclic alkylthio radical which may be substituted, a straight, branched or cyclic alkenyl radical which may be substituted, a straight, branched or cyclic alkenyloxy radical which may be substituted, a straight, branched or cyclic alkenylthio radical which may be substituted, a substituted or unsubstituted aralkyl radical, a substituted or unsubstituted aralkyloxy radical, a substituted or unsubstituted aralkylthio radical, a substituted or unsubstituted aryl radical, a substituted or unsubstituted aryloxy radical, a substituted or unsubstituted arylthio radical, a substituted or unsubstituted amino radical, a cyano radical, a hydroxyl radical, a —COOM1 radical (wherein M1 is a hydrogen atom, a straight, branched or cyclic alkyl radical which may be substituted, a straight, branched or cyclic alkenyl radical which may be substituted, a substituted or unsubstituted aralkyl radical, or a substituted or unsubstituted aryl radical), a —COM2 radical (wherein M2 is a hydrogen atom, a straight, branched or cyclic alkyl radical which may be substituted, a straight, branched or cyclic alkenyl radical which may be substituted, a substituted or unsubstituted aralkyl radical, a substituted or unsubstituted aryl radical, or an amino radical), or a —OCOM3 radical (wherein M3 is a straight, branched or cyclic alkyl radical which may be substituted, a straight, branched or cyclic alkenyl radical which may be substituted, a substituted or unsubstituted aralkyl radical, or a substituted or unsubstituted aryl radical), and at least two adjoining radicals selected from among R1 to R6, R21 and R22 may bond or fuse together to form a substituted or unsubstituted carbocyclic aliphatic ring, aromatic ring or fused aromatic ring with the carbon atoms on which they substitute,
• wherein X is Cl, Br or I, R1 to R8, R31 and R32 each are a hydrogen atom, a straight, branched or cyclic alkyl radical which may be substituted, a straight, branched or cyclic alkoxy radical which may be substituted, a straight, branched or cyclic alkylthio radical which may be substituted, a straight, branched or cyclic alkenyl radical which may be substituted, a straight, branched or cyclic alkenyloxy radical which may be substituted, a straight, branched or cyclic alkenylthio radical which may be substituted, a substituted or unsubstituted aralkyl radical, a substituted or unsubstituted aralkyloxy radical, a substituted or unsubstituted aralkylthio radical, a substituted or unsubstituted aryl radical, a substituted or unsubstituted aryloxy radical, a substituted or unsubstituted arylthio radical, a substituted or unsubstituted amino radical, a cyano radical, a hydroxyl radical, a —COOM1 radical (wherein M1 is a hydrogen atom, a straight, branched or cyclic alkyl radical which may be substituted, a straight, branched or cyclic alkenyl radical which may be substituted, a substituted or unsubstituted aralkyl radical, or a substituted or unsubstituted aryl radical), a —COM2 radical (wherein M2 is a hydrogen atom, a straight, branched or cyclic alkyl radical which may be substituted, a straight, branched or cyclic alkenyl radical which may be substituted, a substituted or unsubstituted aralkyl radical, a substituted or unsubstituted aryl radical, or an amino radical), or a —OCOM3 radical (wherein M3 is a straight, branched or cyclic alkyl radical which may be substituted, a straight, branched or cyclic alkenyl radical which may be substituted, a substituted or unsubstituted aralkyl radical, or a substituted or unsubstituted aryl radical), and at least two adjoining radicals selected from among R1 to R8, R31 and R32 may bond or fuse together to form a substituted or unsubstituted carbocyclic aliphatic ring, aromatic ring or fused aromatic ring with the carbon atoms on which they substitute.