The present invention relates to a process to produce compounds of the formula (1) which are suitable for use in electronic devices, as well as to intermediate compounds of formula (Int-1) and compounds of formula (1-1) and (1-2) obtained via the process. These compounds are particularly suitable for use organic electroluminescent devices. The present invention also relate to electronic devices, which comprise these compounds.

The present invention relates to a process to produce compounds of the formula (1) which are suitable for use in electronic devices, as well as to intermediate compounds of formula (Int-1) and compounds of formula (1-1) and (1-2) obtained via the process. These compounds are particularly suitable for use organic electroluminescent devices. The present invention also relate to electronic devices, which comprise these compounds.

The present invention relates to a process to produce compounds of the formula (1) which are suitable for use in electronic devices, as well as to intermediate compounds of formula (Int-1) and compounds of formula (1-1) and (1-2) obtained via the process. These compounds are particularly suitable for use organic electroluminescent devices. The present invention also relate to electronic devices, which comprise these compounds.

The present application discloses a 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-based phosphine ligand, an intermediate, a preparation method and uses thereof. The compound of phosphine ligand is a compound having a structure represented by formula I or formula II, or an enantiomer, a raceme, or diastereomer thereof. The phosphine ligand can be prepared via a preparation scheme in which the cheap and easily available 6,6′-dihydroxyl-3,3,3′,3′-tetramethyl-1,1′-spirobiindane is used as a raw material and the compound represented by formula III serves as the key intermediate. The new phosphine ligand developed by the present application can be used in catalytic organic reaction, in particular as a chiral phosphine ligand that is widely used in many asymmetric catalytic reactions including asymmetric hydrogenation and asymmetric allyl alkylation, and thus it has economic practicability and industrial application prospect. ##STR00001##

The present application discloses a 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-based phosphine ligand, an intermediate, a preparation method and uses thereof. The compound of phosphine ligand is a compound having a structure represented by formula I or formula II, or an enantiomer, a raceme, or diastereomer thereof. The phosphine ligand can be prepared via a preparation scheme in which the cheap and easily available 6,6′-dihydroxyl-3,3,3′,3′-tetramethyl-1,1′-spirobiindane is used as a raw material and the compound represented by formula III serves as the key intermediate. The new phosphine ligand developed by the present application can be used in catalytic organic reaction, in particular as a chiral phosphine ligand that is widely used in many asymmetric catalytic reactions including asymmetric hydrogenation and asymmetric allyl alkylation, and thus it has economic practicability and industrial application prospect. ##STR00001##

An organic compound is represented by formula (1). In the formula (1), R.sub.1 to R.sub.24 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a silyl group, and a cyano group. ##STR00001##

Provided is a method that allows for a safer production of a naphthylsilole for use as a starting material for GNR, which involves reacting a compound of formula (1):

##STR00001##

(wherein R.sup.1a and R.sup.1b are the same or different and represent a hydrogen atom, an alkyl group, a cycloalkyl group, a (poly)ether group, an ester group, a halogen atom, an aromatic hydrocarbon group, or a heterocyclic group; R.sup.1a and R.sup.1b are optionally bound to each other to form a ring; R.sup.2 represents an aromatic hydrocarbon ring or a heterocyclic ring; and X represents a bromine or iodine atom) with a lanthanide- and lithium-containing ate complex to produce a lanthanide complex of the compound of formula (1); and then reacting it with a silyl compound of formula (2):

R.sup.3aR.sup.3bSiCl.sub.2  (2)

(wherein R.sup.3a and R.sup.3b are the same or different and represent an optionally branched C.sub.1-C.sub.4 alkyl group or a phenyl group).

Provided is a method that allows for a safer production of a naphthylsilole for use as a starting material for GNR, which involves reacting a compound of formula (1):

##STR00001##

(wherein R.sup.1a and R.sup.1b are the same or different and represent a hydrogen atom, an alkyl group, a cycloalkyl group, a (poly)ether group, an ester group, a halogen atom, an aromatic hydrocarbon group, or a heterocyclic group; R.sup.1a and R.sup.1b are optionally bound to each other to form a ring; R.sup.2 represents an aromatic hydrocarbon ring or a heterocyclic ring; and X represents a bromine or iodine atom) with a lanthanide- and lithium-containing ate complex to produce a lanthanide complex of the compound of formula (1); and then reacting it with a silyl compound of formula (2):

R.sup.3aR.sup.3bSiCl.sub.2  (2)

(wherein R.sup.3a and R.sup.3b are the same or different and represent an optionally branched C.sub.1-C.sub.4 alkyl group or a phenyl group).

Provided is a method that allows for a safer production of a naphthylsilole for use as a starting material for GNR, which involves reacting a compound of formula (1):

##STR00001##

(wherein R.sup.1a and R.sup.1b are the same or different and represent a hydrogen atom, an alkyl group, a cycloalkyl group, a (poly)ether group, an ester group, a halogen atom, an aromatic hydrocarbon group, or a heterocyclic group; R.sup.1a and R.sup.1b are optionally bound to each other to form a ring; R.sup.2 represents an aromatic hydrocarbon ring or a heterocyclic ring; and X represents a bromine or iodine atom) with a lanthanide- and lithium-containing ate complex to produce a lanthanide complex of the compound of formula (1); and then reacting it with a silyl compound of formula (2):

R.sup.3aR.sup.3bSiCl.sub.2  (2)

(wherein R.sup.3a and R.sup.3b are the same or different and represent an optionally branched C.sub.1-C.sub.4 alkyl group or a phenyl group).

Disclosed is a method for producing a mono-cross-coupled aromatic compound (3-1) having one less leaving group than an aromatic compound (1) having at least two leaving groups, the method comprising: preparing the aromatic compound (1) having at least two leaving groups; preparing a compound (2) capable of undergoing a cross-coupling reaction selected from an aromatic boronic acid (2-1), an aromatic amino compound (2-2), a diboronic acid ester (2-3), an aromatic compound (2-4) having a hydroxyl group and an aromatic compound (2-5) having a thiol group; and performing a cross-coupling reaction of the aromatic compound (1) having at least two leaving groups with the compound (2) in the presence of a palladium catalyst and a base, in the absence of a solvent.