Organic light-emitting devices - Issued patents / Published patent applications

The invention is a new method of synthesizing Ruddlesden-Popper perovskites with blue emission, which can be applied in blue LED devices with enhanced optical property and stability.

PCT Patent related to the development of gold(III) compounds with aryl auxilliary ligand and their applications for OLEDs.

US Non-Provisional Patent related to the development of gold(III) compounds with aryl auxilliary ligand and their applications for OLEDs.

PCT Patent related to the development of gold(III) compounds with Group 14 element-containing ligand and their applications for OLEDs.

Chinese Patent related to the development of gold(III) compounds with tetradentate ligand and their applications for OLEDs.

US Non-Provisional Patent related to the development of gold(III) compounds with tetradentate ligand and their applications for OLEDs.

A novel class of saturated or conjugated dendrimers containing at least one strong sigma-donating group coordinated to cyclometalated tridentate gold(III) compounds having the chemical structure depicted by generic formula: wherein: (a) [Au] is a cyclometalated tridentate gold(III) group; (b) Unit A is a sigma-donating chemical group; (c) Unit B is a central part of the dendrons comprising a branch point of component dendrimers; (d) Unit C is optional surface groups or dendrons of the dendrimers; (e) n=0 or 1.

This invention pertains to organo-metallic complexes for opto-electronic and sensory devices and their use in such opto-electronic and sensory devices. The organo-metallic complex (triplet emitter) of the invention consists of a metal center and chelate ligands. At least one of these chelate ligands comprises an aromatic or fused aromatic ring(s). Each of these ligands is covalently substituted with at least one, preferably two charge transport groups (ctg). The metal center can additionally be coordinated by a spectator ligand. The presence of two ctgs at each ligand results in distinct advantages - in particular for applications in organic light emitting diodes (OLEDs) - compared to complexes known in the state of the art: - The charge transport units facilitate hole and/or electron transport to the molecular center and allow for efficient exciton formation directly on the emitter complex. - The presence of the ctgs on each ligand provides a good shielding with respect to interactions to the environment. Thus, emission quenching is strongly reduced and materials with high emission quantum yields are obtained. - The presence of the ctgs on each ligand increases the separations between the emitting cores of different molecules and thus reduces undesired quenching by triplet-triplet annihilation or self-quenching effects. - The complexes of the invention are highly soluble in many organic solvents and thus are well suited for wet-chemical processing.

Embodiments of the invention are directed to luminescent gold(III) compounds contains a bidentate ligand with at least one strong s-donating group, a method of preparation of these compounds and the use of these compounds in organic light emitting devices.. The gold (III) compounds have the chemical structure: Formular (I) wherein: X Is a nitrogen atom; Y is selected from a carbon or a nitrogen atom; A-B is a substituted or unsubstituted cyclometalating ligand (for Y=C) or diimine ligand (for Y=N); where A and B are cyclic structure derivatives; R 1and R2 are optionally substituted carbon donor ligands attached to the gold atom, with the proviso that R1 and R2 are not -CH3, -CH2SiMe3, mesityl, pentaflurophenyl, -CH2C(O)R', -CH(R)SO2CH(R)-, -C6H4N=NC6H5, and wherein R1 and R2 can optionally be combined into a bidentate ligand; and n is greater or equal to zero.

The subject invention is directed to tetradentate bis-(NHC carbenes) alkylene ligand Pt(II) complexes, tetradentate bis-(NHC carbenes) alkylene ligands, and its ligand precursors, for preparation of the Pt(II) complexes. The Pt(II) complexes show a deep blue emission with an improved quantum efficiency and can be used for fabrication of OLEDs with an electroluminescence layer that comprise the bis-(NHC carbenes) alkylene ligand Pt(II) complexes.

A novel class of saturated or conjugated dendrimers containing at least one strong sigma-donating group coordinated to cyclometalated tridentate gold(III) compounds having the chemical structure depicted by generic formula: wherein: (a) [Au] is a cyclometalated tridentate gold(III) group; (b) Unit A is a sigma-donating chemical group; (c) Unit B is a central part of the dendrons comprising a branch point of component dendrimers; (d) Unit C is optional surface groups or dendrons of the dendrimers; (e) n=0 or 1.

Subject matter disclosed herein relates to a series of palladium based materials, their preparation method and their applications in an organic light-emitting diode (OLED).

The current invention relates to novel platinum(II) based organometallic materials. These materials show high emission quantum efficiencies and low self-quenching constant. Also provided are high efficiency, green to orange emitting organic light-emitting diode (OLED) that are fabricated using platinum(II) based organometallic materials as the light-emitting material. The organometallic materials of the invention are soluble in common solvents; therefore, solution process methods such as spin coating and printing can be used for device fabrication. The devices fabricated from these materials show low efficiency roll-off.

A class of luminescent gold(iii) compounds with a tridentate ligand and at least one strong sigma-donating group having the chemical structure represented by the general formula (i): wherein r1-r4 each independently represent the group containing hydrogen, halogen, alkynyl, substituted alkynyl, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxyl, substituted alkoxyl, amino, substituted amino, cyano, nitro, alkylcarbonyl, alkoxycarbonyl, arylcarbonyl, aryloxycarbonyl, mono- or dialkylaminocarbonyl, alkylcarbonyloxy, arylcarbonyloxy, aryloxy, alkoxycarbonyl, aryloxycarbonyloxy group, and the like; x, y and z each independently represent a heteroatom or a carbon; represents an aromatic or heterocyclic 5- or 6-membered ring; alpha and beta each independently represent a bridge for an aromatic or heterocyclic 5- or 6-membered ring or represent a break for non-cyclic moiety; c-x, c-y and c-z each independently represent a single bond or double bond; n represents a zero or an integer; p, q and r represent positive integers.

Described are novel platinum (II) containing organometallic materials. These materials show green to orange emissions with high emission quantum efficiencies. Using the materials as emitting materials; pure green emitting organic light-emitting diodes can be fabricated. Since the novel platinum (II) containing organometallic materials are soluble in common solvents, solution process methods such as spin coating and printing can be used for device fabrication.

The invention provides a class of organometallic complexes comprising a tridentate isoquinoline-pyridine-benzene based ligand, a mono-dentate ligand and a platinum (II) center which show high emission quantum efficiency and good thermal stability. This invention also discloses organometallic complexes in organic light-emitting diode (OLED) including them.

A method for treatment of cancer by inhibiting the activity of histone deacetylase, comprising administering to a human in need of such treatment a composition containing a therapeutically effective amount of a gold(III) complex having the structural formula of or a pharmaceutically acceptable salt thereof, wherein: -R is selected from the group consisting of -OH, -CH2OH, C2H4OH, -C3H6OH or -C4H8OH; and X is independently a pharmaceutically acceptable counter-ion.

This invention provides a class of organometallic complexes comprising a tridentate isoquinoline-pyridine-benzene based ligand, a mono-dentate ligand and a platinum (II) center which show high emission quantum efficiency and good thermal stability. This invention also discloses organometallic complexes in organic light-emitting diode (OLED) including them.

Highly fluorescent metallo-supramolecules based on terpyridine-based monomers and transition metals have been obtained. These robust supramolecules provide high quantum yields with emissions from violet to blue, green or yellow color. They have emerged as promising emitters for polymeric light-emitting diodes (pleds) due to desirable properties such as high luminance, high purity, low cost, and good thermal stabilities. The supramolecule has molecular structure represented by the formula wherein m represents group ib, iib viia, viiia or lanthanide metals; r is independently in each occurrence and is selected from the group consisting of hydrogen, halogen, alkyl, substituted alkyl, aryl, substituted aryl, or recognized donor and acceptor groups; x is independently in each occurrence and is nitrogen or carbon atom; r is selected from alkoxy, aryloxy, heteroaryloxy, alkyl, aryl, heteroaryl, alkyl ketone, aryl ketone, heteroaryl ketone, alkylester, arylester, heteroarylester, alkylamide, arylamide, heteroarylamide, alkylthio, arylthio, fluoroalkyl, fluoroaryl, amine, imide, carboxylate, sulfonyl, alkyleneoxy, polyalkyleneoxy, or combination thereof; n is an integer of 1 to 100,000; z is a counter ion and is selected from the group of acetate, acetylacetonate, cyclohexanebutyrate, ethylhexanoate, halide, hexafluorophosphate, hexafluoroacetylacetonate, nitrate, perchlorate, phosphate, sulfate, tetrafluoroborate or fluoromethanesulfonate; y is an integer of 0 to 4.

Highly luminous, thermally stable and moisture-resistant light-emitting materials derived from quadridentate ONNO-type ligands and a Group 10 metal were employed as emissive dopants in organic light-emitting devices. The dopants have molecular structures represented by the formula I and II: wherein M represents Group 10 metal (including platinum) and R1-R14 are each independently selected from the group consisting of hydrogen; halogen; alkyl; substituted alkyl; aryl; substituted aryl, with substitutents selected from the group consisting of halogen, lower alkyl and recognized donor and acceptor groups.

Materials containing one or more borazine rings are employed as materials for electroluminescent devices. The compounds have molecular structures represented by the following formula: in which R1-R6 are independently a metal; a whole or part of an optionally substituted borazine ring; hydrogen; halogen; hydroxyl; optionally substituted alkyl, cycloalkyl, aryl, acyl, alkoxy, acyloxy, amino, acylamino, aralkyl, cyano, carboxyl, thio, vinyl, styryl, aminocarbonyl, carbamoyl, aryloxycarbonyl, phenoxycarbonyl, or alkoxycarbonyl, as well as recognized donor and acceptor groups. The compounds have high thermal stability as well as hole and electron mobilities.

Disclosed Are Electrophosphorescent Organic Metal Complexes With Formula (I) Or (Ii), Of Either Geometrical Isomers, Comprising Two Bidentate Nn-Type Ligandsor A Tetradentate Nnnn-Type Ligand, And A Transition Metal. These Electrophosphorescent Materials Are Valuable To The Application In Organic Light-Emitting Devices (Oleds), Including Red-, Orange-, Or Yellow-Light Oleds.

Disclosed herein are novel light-emitting materials of Formula I and II below. These new complexes are synthesized and found to be sufficiently stable to allow sublimation and vacuum deposition. These new emitters are electrophosphorescent and can be used in organic light-emitting devices (OLEDs) for device elements capable of emitting light of color ranging from orange to red with high-efficiency and high-brightness. wherein E=Group 16 elements (including sulphur); M=Group 10 metal (including platinum); R1-R14 are each independently selected from the group consisting of hydrogen; halogen; alkyl; substituted alkyl; aryl; substituted aryl, with substituents selected from the group consisting of halogen, lower alkyl and recognized donor and acceptor groups.; R1 can also be selected from (C[identical to]C)nR15, where (C[identical to]C) represents a carbon-carbon triple bond (acetylide group), n is selected from 1 to 10, and R15 is selected from alkyl, aryl, substituted aryl, and tri(alkyl)silyl.

Materials containing one or more borazine rings are employed as materials for electroluminescent devices. The compounds have molecular structures represented by the following formula: in which R1-R6 are independently a metal; a whole or part of an optionally substituted borazine ring; hydrogen; halogen; hydroxyl; optionally substituted alkyl, cycloalkyl, aryl, acyl, alkoxy, acyloxy, amino, acylamino, aralkyl, cyano, carboxyl, thio, vinyl, styryl, aminocarbonyl, carbamoyl, aryloxycarbonyl, phenoxycarbonyl, or alkoxycarbonyl, as well as recognized donor and acceptor groups. The compounds have high thermal stability as well as hole and electron mobilities.

Disclosed are emissive materials of formula (i) or (ii), comprising two bidentate no-type ligands, or a tetradentate noon-type ligand, and a transition metal. The emissive materials are useful as electrophosphorescent emitters in organic light-emitting devices. Also disclosed are methods for preparing organic light-emitting diodes comprising these emissive materials, and the use of such diodes as white and yellow organic light-emitting devices.

A luminous organic metal material is synthesized, and has stability enough for sublimation and vacuum deposition is electrically phosphorescent, and can be used for organic LEDs (OLEDs) because of its colour from organe to red, high efficiency and high brightness. This new-light emitting material of formulas I and II is disclosed.

A luminescent sensory material for the detection of the presence of organo-halogen compounds is described. This material is based on a platinum chromophore functionalized with pyridylacetylide ligands, as shown in formulae i and ii below. These complexes exhibit positive luminescence upon exposure to the vapors of organ-halogen compounds like ch2cl2 or chcl3 with high selectivity over non-chlorinated common organic vapors. Direct relationships between vapor concentration and luminescence intensity are established using thin films prepared from these complexes.