The present disclosure provides a new series of compounds exhibiting high fluorescence quantum yields in the solid state. In one embodiment, the compounds include a series of 2,3,4,5-tetraphenylgermoles with the same or different 1,1-substituents. In another embodiment, substituted germafluorenes, germa-fluoresceins/rhodamines, and germapins are described. These germanium heterocycles possess ideal photophysical and thermostability properties, which makes them excellent candidates for chemical or biological sensors, host materials for electroluminescent devices and solar cells, and emissive and/or electron-transport layer components in organic light emitting diode devices.

The invention relates to small, conjugatable, orthogonal and tunable fluorophores for imaging of small bioactive molecules. The invention further relates to processes for the preparation of the compounds, and uses of the compounds in therapeutic, diagnostic, surgery and analytical applications. The invention provides a compound of formula (I), a derivative or a salt thereof. Wherein X is selected from the group consisting of NH, O, S, SeR5R6, CR7R8; R1 is selected from the group consisting of amines, alcohols, thiols, thiophenols, selenols, selenophenols and aryl groups; R2 and R3 are independently H or a halogen; R4 tis either H, nitro or cyano; R5 is either absent or methyl or oxygen; R6 is either absent or methyl or oxygen; and R7 and R8 are independently selected from the group consisting of linear or cyclic alkyl groups containing halogen, amino, cyano or carboxylic ester substituents, and alkyl aryl groups.

##STR00001##

The present invention discloses donor-acceptor structured, aggregated-induced emission fluorescent compounds with deep-red (DR) or near-infrared (NIR). The present invention also shows application in bio-imaging or optoelectronic devices with the fluorescent compounds.

A process for the preparation of a disubstituted diaryloxybenzoheterodiazole compound having general formula (XII): ##STR00001## wherein: Z represents a sulfur atom, an oxygen atom, a selenium atom; or a group NR.sub.6 wherein R.sub.6 is selected from linear or branched C.sub.1-C.sub.20 alkyl groups, or from optionally substituted aryl groups; R.sub.2 and R.sub.3, identical or different, represent a hydrogen atom, provided that R.sub.1 does not represent a hydrogen atom; or R.sub.1, R.sub.2 and R.sub.3 are selected from linear or branched C.sub.1-C.sub.20 alkyl groups optionally containing heteroatoms, optionally substituted cycloalkyl groups, optionally substituted aryl groups, optionally substituted, linear or branched C.sub.1-C.sub.20 alkoxy groups, optionally substituted phenoxy groups, or a cyano group; or R.sub.1 and R.sub.2, may optionally be bound together so as to form, together with carbon atoms to which R.sub.1 and R.sub.2 are bound, a saturated, unsaturated, or aromatic, cyclic or a polycyclic system containing from 3 to 14 carbon atoms, optionally containing one or more heteroatoms selected from oxygen, sulfur, nitrogen, silicon, phosphorus, or selenium; or R.sub.2 and R.sub.3 may optionally be bound together so as to form, together with carbon atoms to which R.sub.2 and R.sub.3 are bound, a saturated, unsaturated, or aromatic, cyclic or a polycyclic system containing from 3 to 14 carbon atoms, saturated, unsaturated, or aromatic, optionally containing one or more heteroatoms selected from oxygen, sulfur, nitrogen, silicon, phosphorus, or selenium; wherein R.sub.a and R.sub.b, which are different, represent a hydrogen atom; or are selected from linear or branched C.sub.1-C.sub.20 alkyl groups optionally containing heteroatoms, optionally substituted cycloalkyl groups, optionally substituted aryl groups, optionally substituted linear or branched C.sub.1-C.sub.20 alkoxy groups, optionally substituted phenoxy groups, —COOR.sub.c groups wherein R.sub.c is selected from linear or branched C.sub.1-C.sub.20 alkyl groups, —CON(R.sub.c).sub.2, wherein R.sub.c has the same meanings described above, or —N(R.sub.c).sub.2 groups wherein R.sub.c has the same meanings described above.

Novel phosphorescent metal complexes containing ligands having the Formula I: ##STR00001##
bearing either a naphthalene or other fused heterocycle moieties such as benzofuran and benzothiophene useful as emitters in OLEDs and improve the device efficiency and the FWHM of the emission are disclosed.

Compounds of General Formula I may harvest electrogenerated excitons via metal-assisted delayed fluorescence (MADF). The compounds have utility in light emitting diodes and light emitting devices.

A compound having a formula M(L.sub.A)(L.sub.B)(L.sub.C) is disclosed. Each of ligands L.sub.A and L.sub.B are mono-anionic bidentate ligands coordinated to metal M forming a 5-member cyclometalated ring. Ligands L.sub.A and L.sub.B are covalently linked by a first linking group, where there is at least one loop of M-L.sub.A-first linking group-L.sub.B-M having only carbocyclic or heterocyclic groups in the loop other than M. Wherein the first linking group includes multiple aliphatic or aromatic rings that are separated by at least one single bond, where each ring in the first linking group is part of the backbone of the loop. Devices, such as organic light emitting diodes, including the compounds are also disclosed.

A compound comprising a ligand L.sub.A coordinated to a metal M ##STR00001## wherein ring A, ring T, and ring W are independently selected from a 5-membered or 6-membered heterocyclic or carbocyclic ring, and the ring W is fused to the ring T. The metal compounds having a ligand L.sub.A can be found in an OLED that includes an organic layer positioned between an anode and a cathode where the organic layer comprises a metal compound above having a ligand L.sub.A disclosed herein. We also describe a consumer product comprising the OLED.

A dual host system for OLEDs that contains hole-transporting indolocarbazole and electron-transporting indolocarbazole exhibiting superior performance in the OLEDs is disclosed.

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

##STR00001##

is provided. In Formula I, each of X.sup.B, X.sup.1 to X.sup.4 is C or N; two adjacent R.sup.A are joined together to form a structure of Formula II,

##STR00002##

each one of moiety B and moiety C is a monocyclic ring or polycyclic ring system; Y is selected from a group of divalent single-atom linkers; each R, R′, R″, R.sup.A, R.sup.B, and R.sup.C is hydrogen or a General Substituent; the first ligand L.sub.A is coordinated to metal M through the dashed lines; metal M may be coordinated to other ligands; and any two substituents may be joined or fused to form a ring. Formulations, OLEDs, and consumer products including the compound are also provided.