The present invention relates to a preparation method for and an application of a chiral spirocyclic phosphine-nitrogen-phosphine tridentate ligand SpiroPNP and an iridium catalyst Ir-SpiroPNP thereof. The chiral spirocyclic phosphine-nitrogen-phosphine tridentate ligand is a compound represented by formula I, or a racemate or optical isomer thereof, or a catalytically acceptable salt thereof, and the main structural feature is a phosphine ligand having a chiral spiro indene skeleton and a large sterically hindered substituent. The chiral spirocyclic phosphine-nitrogen-phosphine tridentate ligand can be synthesized into a chiral starting material from a 7-diaryl/alkylphosphino-7′-amino-1,1′-spirodihydroindenyl compound having a spiro ring skeleton. The iridium catalyst of the chiral spirocyclic phosphino-7′-amino-1,1′-spirodihydroindenyl compound having a sprio ring skeleton. The iridium catalyst of the chiral spirocyclic phosphine-nitrogen-phosphine tridentate ligand is a compound represented by formula II, or a racemate or optical isomer thereof, or a catalytically acceptable salt thereof. The iridium catalyst can be used to catalyze the asymmetric catalytic hydrogenation of carbonyl compounds, and especially in the asymmetric catalytic hydrogenation of simple dialkyl ketones. Said catalyst exhibits high yield (>99%) and enantioselectivity (up to 99.8% ee), thus having practical value.

##STR00001##

A compound having a first ligand L.sub.A of Formula I,

##STR00001##

is provided. In Formula I, Z is C or N; at least one of X.sup.1 to X.sup.5 is N, and the remainder are C; if X.sup.1 is N, then X.sup.5 is C; K is selected from the group consisting of a direct bond, O, S, N(R.sup.α), P(R.sup.α), B(R.sup.α), C(R.sup.α)(R.sup.β), and Si(R.sup.α)(R.sup.β); each R.sup.α, R.sup.β, R.sup.A and R.sup.B is a hydrogen or a General Substituent; L.sub.A is coordinated to a metal M; and Ring A coordinates to M through a metal carbene bond. Formulations, OLEDs, and consumer products containing the compound are also provided.

A 1, 4 bidentate ligand comprising first and second ligand centres, wherein the first ligand centre is an sp.sup.2-hybridised carbon or a nitrogen atom; wherein the second ligand centre is a nitrogen atom in a five- or six-membered aromatic or hetero-aromatic ring, said ring having a substantially linear substituent T.sup.1 meta or para to the nitrogen atom; wherein T.sup.1 has the formula 1:
—Ar.sup.1.sub.a—Y.sup.1.sub.b—Ar.sup.2—[Y.sup.2.sub.c—Ar.sup.2].sub.d—S—B  (1) and wherein T.sup.1 is attached to the ring by X.sup.1, wherein X.sup.1 is a bond, a methylene group, a substituted methylene group, an oxygen atom or a sulphur atom, wherein each Ar.sup.1 and Ar.sup.2 are independently selected from the group of C.sub.6 to C.sub.20 aromatic and C.sub.4 to C.sub.20 heteroaromatic groups, wherein Y.sup.1 and each Y.sup.2 is independently an optionally substituted C.sub.2 or acetonitrile trans double-bond linking moiety, wherein a is 0, 1, 2 or 3, wherein b is 0, 1 or 2, wherein each c is independently 0, 1 or 2, wherein d is 0, 1, 2, 3 or 4, S is a flexible spacer, and B represents a moiety having one or more cross-linkable functionalities. Network polymers, complexes, compositions, and devices based on this ligand. Method for forming devices based on this ligand.

A composition that contains an iridium complex and an isomer of the iridium complex, in which the amount of the isomer of the iridium complex is decreased. The iridium complex is a homo-N-trans (HNT) iridium complex having an iridium atom, and a first ligand, a second ligand, and a third ligand that are bonded to the iridium atom. The isomer has an iridium atom, a fourth ligand, a fifth ligand, and the third ligand. The composition ratio of the isomer relative to a total of the iridium complex and the isomer is 1.0% or less.

A novel organometallic complex with high reliability is provided. A light-emitting element includes an EL layer between a pair of electrodes. The EL layer includes at least a light-emitting layer. The light-emitting layer contains an organometallic complex. The organometallic complex includes a first ligand and a second ligand which are coordinated to a central metal. The HOMO is distributed over the first ligand, and the LUMO is distributed over the second ligand. The first ligand and the second ligand are cyclometalated ligands.

Provided are compounds having a ligand L.sub.A of Formula I

##STR00001##

that are useful as emissive compounds in organic light emitting devices.

Metal coordination complexes comprising an iridium atom coordinated to at least one diazabutadiene based ligand having a structure represented by:

##STR00001##

where R1 and R4 are independently selected from the group consisting of C1-C4 alkyl and amino groups, and each of R2 and R3 are independently selected from the group consisting of H, C1-C3 alkyl, or amino groups are described. Processing methods using the metal coordination complexes are also described.

A method for producing a halogen-crosslinked iridium dimer with increased purity that is used as a precursor in production of a cyclometalated iridium complex useful as a phosphorescent material for organic electroluminescent devices, organic electrochemiluminescent devices, luminescent sensors, photosensitizing pigments, photocatalysts, luminescent probes, various light sources, and the like. The halogen-crosslinked iridium dimer is represented by the following formula: ##STR00001##
In this formula, each X represents a halogen atom, each CyA represents an optionally substituted five- or six-membered cyclic ring containing nitrogen atoms, and is linked to iridium via the nitrogen atoms, and each CyB represents an optionally substituted five- or six-membered ring containing carbon atoms, and is linked to iridium via the carbon atoms. CyA and CyB can be linked together to form an optionally substituted ring.

Through the use of a rhodamine appended chelate, a versatile strategy has been demonstrated to generate mitochondria-targeting photosensitizers via the incorporation of variety of luminescent transition metal systems. The generation of triplet excited state of rhodamine moiety endows the complexes with mitochondria-targeting photosensitizing ability to form singlet oxygen (.sup.1O.sub.2) for use as photodynamic therapy (PDT) agent. The combination of rhodamine organic dye and luminescent transition metal centers in such hybrid systems exhibits the synergistic merits, including low dark cytotoxicity, selective tumor cell uptake, high molar absorptivity for low-energy excitation in the visible region, and high photostability.

The present invention provides biologically active compounds and methods to obtain biologically active compounds that can be used as photosensitizers for diagnostic and therapeutic applications, particularly for PDT of cancer, infections and other hyperproliferative diseases, fluorescence diagnosis and PDT treatment of non-tumorous indications such as arthritis, inflammatory diseases, viral or bacterial infections, dermatological, ophthalmological or urological disorders. As the compounds exhibit also toxicity against targets (tumor cells, bacteria, inflammation-related cells) without light these biologically active compounds may also be used for the light-independent treatment of such indications. Preferred embodiments of the present invention consist of methods to synthesize metal or half-metal complex structures incorporating one or more substituted 2,3,5,6-tetrafluorophenyl-dipyrromethene (2,3,5,6-tetrafluorophenyldipyrrin) units. These dipyrromethenes (dipyrrins) can carry a variety of different substituents in the 4-position enabling a fine tuning of their biological or amphiphilic/hydrophilic properties. Another object of the present invention is to provide amphiphilic compounds with a higher membrane affinity and increased efficacy.