Metal-assisted delayed fluorescence emitter for organic light-emitting diodes

Abstract

This application relates to metal-assisted delayed fluorescence emitters for organic light-emitting diodes. The compound of general formula I can harvest electro-generated excitons through metal-assisted delayed fluorescence (MADF). The compound is used in light-emitting diodes and light-emitting devices.

Description

[0001] Cross - Reference to Related Applications

[0002] This application claims priority to U.S. Provisional Application No. 63 / 026,806, filed May 19, 2020, which is incorporated herein by reference in its entirety.

[0003] Statement Regarding Federally Sponsored Research or Development

[0004] This invention was made with government support under DE-EE0008721 awarded by the U.S. Department of Energy. The government has certain rights in this invention. Technical Field

[0005] This application generally relates to metal-assisted delayed fluorescence emitters. Background Art

[0006] For various reasons, optoelectronic devices utilizing organic materials have become increasingly desirable. Many of the materials used to fabricate such devices are relatively inexpensive, so organic optoelectronic devices have the potential for a cost advantage over inorganic devices. Additionally, the inherent properties of organic materials, such as their flexibility, can make them well-suited for specific applications, such as fabrication on flexible substrates. Examples of organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, organic materials can have performance advantages over conventional materials. For example, the wavelength of light emitted by an organic emissive layer can generally be easily tuned with appropriate dopants.

[0007] In recent years, due to the outstanding advantages of organic light-emitting diodes (OLEDs), such as high color quality, wide viewing angle, low-cost fabrication, low power consumption, fast response speed, and high electron-to-photon conversion efficiency, they have attracted great attention in both academic and industrial fields. Most organic light-emitting diodes (OLEDs) are phosphorescent OLEDs using iridium (Ir), palladium (Pd), and platinum (Pt) complexes because these metal complexes have strong spin-orbit coupling, which can emit light efficiently from triplet excited states and achieve nearly 100% internal efficiency.

[0008] There is still a need in the art for effective and stable OLED components. The present invention addresses this unmet need. Summary of the Invention

[0009] In one aspect, the present disclosure relates to compounds of general formula I;

[0010]

[0011] Wherein:

[0012] M represents Pt(II) or Pd(II);

[0013] R 1 , R 2 , R 3 , R 4 , R 5 and R 6 Each of is independently absent or present as a single substituent or multiple substituents as valence permits, and R 1 , R 3 , R 4 , R 5 , R 6 and R 8 Each of the above independently represents hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazine; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, urea, phosphoramide, silanyl, polymer; or any conjugate or combination thereof;

[0014] There are two adjacent substituents R 2 , with the group R 2 Bound group Y 4a , Y 4b , Y 4c or Y 4d are each C, and the two adjacent groups R 2 Represented by formula A:

[0015]

[0016] Wherein * represents a bond of the general formula I;

[0017] X represents a single bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 、C=O、SiR 7 R 8 ,GeR 7 R 8 NR 7 , PR 7 , PR 7 R 8 , R 7 P=O、AsR 7 , R 7 As=O、S=O、SO 2 、Se=O、SeO2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi = O or BiR 7 , or X is absent, where when X is absent, L 4 and the ring containing Z 2 have no bond between them;

[0018] X 1 represents a single bond, O, S, Se, P = O, As = O, Bi = O, CR 7 R 8 , C = O, SiR 7 R 8 , GeR 7 R 8 , NR 7 , PR 7 , PR 7 R 8 , R 7 P = O, AsR 7 , R 7 As = O, S = O, SO 2 , Se = O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi = O or BiR 7 ;

[0019] R 7 and each occurrence of R 8 is independently absent or, where valency permits, present as a single substituent or multiple substituents, and each of R 7 and R 8 independently represents hydrogen, deuterium, halogen, hydroxy, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxy, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; or R 1 , R2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 Any two of them represent a covalent bond;

[0020] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , X and X 1 Any two of them can together form a fused ring;

[0021] A, B, C, and D each independently represent C, N, O, or S;

[0022] Y 1 and Y 2 each independently represent hydrogen, deuterium, halogen, hydroxyl, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; where Y 1 and Y 2 can optionally together form a fused aromatic or heteroaromatic ring;

[0023] Y 3a , Y 3b , Y 4a , Y 4b , Y 4c , Y 4d , Y 4e , Y 4f , Y 4g , Y 4h each independently represent C or N;

[0024] Z 1 , Z 2 , Z 3 and Z 4 each independently represent C or N;

[0025] L 4 , L 5 and L6 each independently represents a 5- to 10-membered aryl, heteroaryl, fused aryl or fused heteroaryl;

[0026] L 5 present or absent;

[0027] V 1 and V 2 are each independently present or absent; wherein V 1 and V 2 each, if present, independently represents a covalent bond, O, S, Se, P═O, As═O, Bi═O, CR 7 R 8 、C═O、SiR 7 R 8 、GeR 7 R 8 、NR 7 、PR 7 、PR 7 R 8 、R 7 P═O、AsR 7 、R 7 As═O、S═O、SO 2 、Se═O、SeO 2 、BR 7 、BR 7 R 8 、AlR 7 、AlR 7 R 8 、R 7 Bi═O or BiR 7 ;wherein when V 1 is absent, then L 4 does not bind to L 5 ; and when V 2 is absent, then L 6 does not bind to L 5 ;

[0028] V 3 is present or absent, wherein V 3 , if present, represents a covalent bond, C, N, Si, O, S, Ge, P, As, Se, B, Al or Bi, or, if valence permits, each independently represents CR 7 、SiR 7 、GeR 7 、NR 7 、P═O、As═O、B、BR 7 、AlR 7 、Bi═O、CR 7 R 8, C=O, SiR 7 R 8 , GeR 7 R 8 , NR 7 , PR 7 , PR 7 R 8 , R 7 , R P=O, AsR 7 , R 7 , R As=O, S=O, SO 2 , Se=O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 , Bi=O or BiR 7 ; wherein when V 3 is absent, then Y 2a binds directly to Y 2b ; and

[0029] In the case where the valence allows, each n is independently an integer.

[0030] In one embodiment, there is provided an organic light emitting diode (OLED) comprising the compound. According to another embodiment, there is provided a light emitting device comprising the light emitting diode. BRIEF DESCRIPTION OF THE DRAWINGS

[0031] The following detailed description of the preferred embodiments of the present disclosure will be better understood when read in conjunction with the accompanying drawings. For the purpose of illustrating the invention, the currently preferred embodiments are shown in the drawings. However, it should be understood that the invention is not limited to the exact arrangements and instrumentalities shown in the embodiments of the drawings.

[0032] Figure 1 is a schematic diagram of an organic light emitting device.

[0033] Figure 2 is a schematic diagram depicting the delayed fluorescence process.

[0034] Figure 3 depicts an exemplary compound.

[0035] Figure 4 is a graph of the photoluminescence of the exemplary compound Pd3O8-cz56.

[0036] Figure 5 is a graph of the photoluminescence of the exemplary compound PtON2-Cz56.

[0037] Figure 6 It is a diagram of the photoluminescence of the exemplary compound PtON2-Sz56.

[0038] Figure 7 It is a diagram of the electroluminescence spectrum (a) and EQE versus luminance (b) of a device using PtON2-Cz56-tbu as the emitter. The general device structure is HATCN(10nm) / NPD(40nm) / BCN34(10nm) / 6% PtON2-Cz56-tbu:mCBP(20nm) / BAlq(10nm) / BPyTP(40nm) / Liq(2nm) / Al. Detailed Description

[0039] This disclosure relates in part to the unexpected discovery that increased conjugation increases the MADF efficiency.

[0040] Definitions

[0041] It should be understood that, for clarity, the drawings and description in this disclosure have been simplified to show elements relevant to a clear understanding of the invention, while eliminating many other elements found in the art related to phosphorescent organic light-emitting devices and the like. Those of ordinary skill in the art will recognize that other elements and / or steps are desirable and / or required for implementing the disclosed embodiments. However, since such elements and steps are well known in the art and since such elements do not contribute to a better understanding of this disclosure, no discussion of such elements and steps is provided herein. The disclosure herein relates to all such variations and modifications of such elements and methods known to those skilled in the art.

[0042] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. Although any methods, materials, and components similar or equivalent to those described herein can be used in the practice or testing of the disclosed embodiments, the preferred methods and materials are described.

[0043] As used herein, each of the following terms has the meaning associated with it in this section.

[0044] The articles "a / an" refer herein to one or more than one (i.e., at least one) grammatical object of the article. For example, "an element" means one element or more than one element.

[0045] As used herein, when referring to measurable values such as amounts, durations, etc., "about" means encompassing variations that are ±20%, ±10%, ±5%, ±1% or ±0.1% from the specified value, as these variations are appropriate.

[0046] Throughout this disclosure, various aspects of the invention may be presented in a range format. It should be understood that the description in range format is merely for convenience and brevity and should not be construed as a rigid limitation on the scope of the invention. Thus, a description of a range should be considered to specifically disclose all the possible sub-ranges as well as the individual numerical values within that range. For example, a description of the range from 1 to 6 should be considered to specifically disclose sub-ranges such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as the individual numbers within that range, such as 1, 2, 2.7, 3, 4, 5, 5.3, 6 and any whole and partial increments therebetween. This applies regardless of the width of the range.

[0047] The components for preparing the compositions of the present disclosure and the compositions themselves used in the methods disclosed herein are disclosed. These materials and other materials are disclosed herein, and it should be understood that while specific references to each and every individual and collective combination and permutation of these compounds may not be explicitly disclosed when combinations, subsets, interactions, groups, etc. of these materials are disclosed, each combination and permutation is specifically contemplated and described herein. For example, if a particular compound is disclosed and discussed and numerous modifications that may be made to a plurality of molecules containing the compound are discussed, then each combination and permutation of the compound and the possible modifications are specifically encompassed unless specifically stated to the contrary. Thus, if a class of molecules A, B, and C and a class of molecules D, E, and F are disclosed and an example of the combined molecule A-D is disclosed, then each molecule is considered individually and collectively, even if each molecule is not individually recited, which means that combinations A-E, A-F, B-D, B-E, B-F, C-D, C-E, and C-F are considered to be disclosed. Similarly, any subset or combination of these is also disclosed. Thus, for example, sub-groups of A-E, B-F, and C-E are considered to be disclosed. This concept applies to all aspects of this application, including but not limited to the steps in the methods of preparing and using the compositions of the invention. Thus, if there are various additional steps that may be performed, it should be understood that each of these additional steps may be performed with any specific embodiment or combination of embodiments of the method of the invention.

[0048] As referred to herein, a linking atom or linking group can link two groups, such as N and C groups. If the valence allows, the linking atom can optionally have other chemical moieties attached thereto. For example, in one aspect, once oxygen is bonded to two groups (e.g., N and / or C groups), since the valence is satisfied, oxygen will not have any other chemical groups attached. On the other hand, when carbon is the linking atom, two additional chemical moieties can be attached to the carbon. Suitable chemical moieties include but are not limited to hydrogen, hydroxy, alkyl, alkoxy, ═O, halogen, nitro, amine, amide, thiol, aryl, heteroaryl, cycloalkyl, and heterocyclic group.

[0049] As used herein, the term "cyclic structure" or like terms refers to any cyclic chemical structure, which includes but is not limited to aryl, heteroaryl, cycloalkyl, cycloalkenyl, and heterocyclic group.

[0050] As used herein, it is contemplated that the term "substituted" includes all permissible substituents of an organic compound. In a broad aspect, permissible substituents include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, and aromatic and non-aromatic substituents of an organic compound. Illustrative substituents include, for example, those described below. For a suitable organic compound, the permissible substituents can be one or more and can be the same or different. For the purposes of this disclosure, a heteroatom (such as nitrogen) can have a hydrogen substituent and / or any permissible substituents of the organic compounds described herein, which will satisfy the valence of the heteroatom. The present disclosure is not intended to be limited in any way by the permissible substituents of the organic compound. Moreover, the terms "substituted" or "substituted with" include the implicit condition that such substitution is consistent with the permissible valences of the substituted atom and the substituents, and the substitution results in a stable compound, e.g., a compound that does not spontaneously undergo transformation (such as by rearrangement, cyclization, elimination, etc.). It is also contemplated that, in certain aspects, unless expressly stated to the contrary, an individual substituent can be further optionally substituted (i.e., further substituted or unsubstituted).

[0051] As used herein, the term "alkyl" is a branched or unbranched saturated hydrocarbon group having from 1 to 24 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, eicosyl, tetracosyl, and the like. The alkyl group can be cyclic or acyclic. The alkyl group can be branched or unbranched. The alkyl group can also be substituted or unsubstituted. For example, the alkyl group can be substituted with one or more groups including but not limited to alkyl, cycloalkyl, alkoxy, amino, ether, halide, hydroxy, nitro, silyl, sulfo-oxo, or mercapto as described herein. "Lower alkyl" is an alkyl group containing from one to six (e.g., one to four) carbon atoms.

[0052] Throughout this specification, the term "alkyl" is generally used to refer to both unsubstituted and substituted alkyl groups; however, substituted alkyl groups are also specifically referred to herein by identifying one or more specific substituents on the alkyl group. For example, the term "haloalkyl" or "halogenated alkyl" specifically refers to an alkyl group substituted with one or more halogen ions (e.g., fluoride, chloride, bromide, or iodide ions). The term "alkoxyalkyl" specifically refers to an alkyl group substituted with one or more alkoxy groups as described below. The term "alkylamino" specifically refers to an alkyl group substituted with one or more amino groups and the like as described below. When the term "alkyl" is used in one instance and a specific term such as "alkyl alcohol" is used in another instance, this does not imply that the term "alkyl" does not also refer to specific terms such as "alkyl alcohol" and the like.

[0053] This practice is also used for other groups described herein. That is, although terms such as "cycloalkyl" refer to both unsubstituted and substituted cycloalkyl moieties, the substituted moieties can also be specifically identified herein; for example, a specific substituted cycloalkyl can be referred to as, for example, "alkylcycloalkyl". Similarly, a substituted alkoxy can be specifically referred to as, for example, "haloalkoxy", and a specific substituted alkenyl can be, for example, "alkenyl alcohol", and the like. Again, the practice of using a general term such as "cycloalkyl" and a specific term such as "alkylcycloalkyl" does not imply that the general term does not also encompass the specific term.

[0054] As used herein, the term "cycloalkyl" is a non-aromatic carbocyclic ring composed of at least three carbon atoms. Examples of cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, and the like. The term "heterocycloalkyl" is a type of cycloalkyl as defined above and is included within the meaning of the term "cycloalkyl", wherein at least one of the carbon atoms in the ring is replaced by a heteroatom such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus. Cycloalkyl and heterocycloalkyl may be substituted or unsubstituted. Cycloalkyl and heterocycloalkyl may be substituted by one or more groups including, but not limited to, alkyl, cycloalkyl, alkoxy, amino, ether, halide, hydroxy, nitro, silyl, sulfo-oxo, or thiol as described herein.

[0055] As used herein, the term "polyalkylene" is a group having two or more CH 2 groups connected to each other. Polyalkylene may be represented by the formula -(CH 2 ) a -, where "a" is an integer from 2 to 500.

[0056] As used herein, the terms "alkoxy" and "alkoxyl" refer to an alkyl or cycloalkyl bonded through an ether bond; that is, "alkoxy" may be defined as -OA 1 , where A 1 is an alkyl or cycloalkyl as defined above. "Alkoxy" also includes polymers of the alkoxy just described; that is, alkoxy may be a polyether such as -OA 1 -OA 2 or -OA 1 -(OA 2 ) a -OA 3 , where "a" is an integer from 1 to 200, and A 1 , A 2 and A 3 are alkyl and / or cycloalkyl.

[0057] As used herein, the term "alkenyl" is a hydrocarbon group having 2 to 24 carbon atoms, and its structural formula contains at least one carbon-carbon double bond. Such as (A 1 A 2 )C=C(A 3 A 4) Asymmetric structures such as these are intended to include both E and Z isomers. This can be assumed in the structural formulas where there are asymmetric alkenes in this text, or can be represented by the bond symbol C═C. The alkenyl group can be substituted by one or more groups including but not limited to alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, azide, nitro, silyl, sulfo-oxo or thiol as described herein.

[0058] As used herein, the term "cycloalkenyl" is a non-aromatic carbocyclic ring composed of at least three carbon atoms and containing at least one carbon-carbon double bond (i.e., C═C). Examples of cycloalkenyl include but are not limited to cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, norbornenyl, etc. The term "heterocycloalkenyl" is a type of cycloalkenyl as defined above and is included within the meaning of the term "cycloalkenyl", wherein at least one of the carbon atoms in the ring is replaced by a heteroatom such as but not limited to nitrogen, oxygen, sulfur or phosphorus. The cycloalkenyl and heterocycloalkenyl can be substituted or unsubstituted. The cycloalkenyl and heterocycloalkenyl can be substituted by one or more groups including but not limited to alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, azide, nitro, silyl, sulfo-oxo or thiol as described herein.

[0059] As used herein, the term "alkynyl" is a hydrocarbon group having 2 to 24 carbon atoms, the structural formula of which contains at least one carbon-carbon triple bond. The alkynyl group can be unsubstituted or substituted by one or more groups including but not limited to alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, azide, nitro, silyl, sulfo-oxo or thiol as described herein.

[0060] As used herein, the term "cycloalkynyl" is a non-aromatic carbocyclic ring composed of at least seven carbon atoms and containing at least one carbon-carbon triple bond. Examples of cycloalkynyl include, but are not limited to, cycloheptynyl, cyclooctynyl, cyclononynyl, and the like. The term "heterocycloalkynyl" is a type of cycloalkynyl as defined above and is included within the meaning of the term "cycloalkynyl", wherein at least one of the carbon atoms in the ring is replaced by a heteroatom such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus. Cycloalkynyl and heterocycloalkynyl may be substituted or unsubstituted. Cycloalkynyl and heterocycloalkynyl may be substituted by one or more groups including, but not limited to, alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, azide, nitro, silyl, sulfo-oxo, or thiol as described herein.

[0061] As used herein, the term "aryl" is a group containing any carbocyclic aromatic group including, but not limited to, benzene, naphthalene, phenyl, biphenyl, phenoxyphenyl, and the like. The term "aryl" also includes "heteroaryl", which is defined as a group containing an aromatic group having at least one heteroatom incorporated within the ring of the aromatic group. Examples of heteroatoms include, but are not limited to, nitrogen, oxygen, sulfur, and phosphorus. Also included within the term "aryl" is the term "non-heteroaryl", which defines a group containing an aromatic group that does not contain a heteroatom. Aryl may be substituted or unsubstituted. Aryl may be substituted by one or more groups including, but not limited to, alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, azide, nitro, silyl, sulfo-oxo, or thiol as described herein. The term "biaryl" is a specific type of aryl and is included within the definition of "aryl". Biaryl refers to two aryl groups joined together by a fused ring structure as in naphthalene or joined by one or more carbon-carbon bonds as in biphenyl.

[0062] As used herein, the term "aldehyde" is represented by the formula -C(O)H. Throughout this specification, "C(O)" is a shorthand notation for a carbonyl group (i.e., C=O).

[0063] As used herein, the term "amine" or "amino" is represented by the formula -NA 1 A 2 wherein A 1 and A 2 may independently be hydrogen or alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, or heteroaryl as described herein.

[0064] As used herein, the term "alkylamino" is represented by the formula -NH(-alkyl), where alkyl is as described herein. Representative examples include, but are not limited to, methylamino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino, (sec-butyl)amino, (tert-butyl)amino, pentylamino, isopentylamino, (tert-pentyl)amino, hexylamino, and the like.

[0065] As used herein, the term "dialkylamino" is represented by the formula -N(-alkyl) 2 where alkyl is as described herein. Representative examples include, but are not limited to, dimethylamino, diethylamino, dipropylamino, diisopropylamino, dibutylamino, diisobutylamino, di(sec-butyl)amino, di(tert-butyl)amino, dipentylamino, diisopentylamino, di(tert-pentyl)amino, dihexylamino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-ethyl-N-propylamino, and the like.

[0066] As used herein, the term "carboxylic acid" is represented by the formula -C(O)OH.

[0067] As used herein, the term "ester" is represented by the formula -OC(O)A 1 or -C(O)OA 1 where A 1 can be alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, or heteroaryl as described herein. As used herein, the term "polyester" is represented by the formula -(A 1 O(O)C-A 2 -C(O)O) or -(A 1 O(O)C-A 2 -OC(O)) a - where A 1 and A 2 can independently be alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, or heteroaryl as described herein, and "a" is an integer from 1 to 500. "Polyester" is a term used to describe a group produced by the reaction between a compound having at least two carboxylic acid groups and a compound having at least two hydroxyl groups.

[0068] As used herein, the term "ether" is represented by the formula A 1 OA 2 where A 1 and A 2 can independently be alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, or heteroaryl as described herein. As used herein, the term "polyether" is represented by the formula -(A 1 O-A 2 O) a- represents, wherein A 1 and A 2 can each independently be an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or heteroaryl as described herein, and "a" is an integer from 1 to 500. Examples of polyethers include polyethylene oxide, polypropylene oxide, and polybutylene oxide.

[0069] As used herein, the term "halide" refers to the halogens fluorine, chlorine, bromine, and iodine.

[0070] As used herein, the term "heterocyclic group" refers to monocyclic and polycyclic non-aromatic ring systems, and as used herein, "heteroaryl" refers to monocyclic and polycyclic aromatic ring systems: wherein at least one of the ring members is not carbon. The term "heterocyclic group" includes azetidine, dioxane, furan, imidazole, isothiazole, isoxazole, morpholine, oxazole (including 1,2,3-oxadiazole, 1,2,5-oxadiazole, and 1,3,4-oxadiazole), piperazine, piperidine, pyrazine, pyrazole, pyridazine, pyridine, pyrimidine, pyrrole, pyrrolidine, tetrahydrofuran, tetrahydropyran, tetrazine (including 1,2,4,5-tetrazine), tetrazole (including 1,2,3,4-tetrazole and 1,2,4,5-tetrazole), thiadiazole (including 1,2,3-thiadiazole, 1,2,5-thiadiazole, and 1,3,4-thiadiazole), thiazole, thiophene, triazine (including 1,3,5-triazine and 1,2,4-triazine), triazole (including 1,2,3-triazole, 1,3,4-triazole), etc.

[0071] As used herein, the term "hydroxy" is represented by the formula -OH.

[0072] As used herein, the term "ketone" is represented by the formula A 1 C(O)A 2 wherein A 1 and A 2 can each independently be an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or heteroaryl as described herein.

[0073] As used herein, the term "azide" is represented by the formula -N 3 as shown.

[0074] As used herein, the term "nitro" is represented by the formula -NO 2 as shown.

[0075] As used herein, the term "nitrile" is represented by the formula -CN.

[0076] As used herein, the term "ureido" refers to a urea group of the formula -NHC(O)NH 2 or -NHC(O)NH-.

[0077] As used herein, the term "phosphoramide" refers to a group of the formula -P(O)(NA 1 A 2 ) 2 wherein A 1 and A 2 can independently be hydrogen or an alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or heteroaryl as described herein.

[0078] As used herein, the term "carbamoyl" refers to an amide group of the formula -CONA 1 A 2 wherein A 1 and A 2 can independently be hydrogen or an alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or heteroaryl as described herein.

[0079] As used herein, the term "sulfamoyl" refers to a group of the formula -S(O) 2 NA 1 A 2 wherein A 1 and A 2 can independently be hydrogen or an alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or heteroaryl as described herein.

[0080] As used herein, the term "silyl" is represented by the formula -SiA 1A 2 A 3 wherein A 1 、A 2 and A 3 can independently be hydrogen or an alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or heteroaryl as described herein.

[0081] As used herein, the term "sulfo-oxo" is represented by the formula -S(O)A 1 、-S(O) 2 A 1 、-OS(O) 2 A 1 or -OS(O) 2 OA 1 wherein A 1 is hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or heteroaryl as described herein. Throughout this specification, "S(O)" is a simplified symbol for S=O. The term "sulfonyl" as used herein refers to a sulfo-oxo group represented by the formula -S(O) 2 A 1 wherein A 1is hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or heteroaryl as described herein. As used herein, the term "sulfone" is represented by formula A 1 S(O) 2 A 2 wherein A 1 and A 2 can independently be an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or heteroaryl as described herein. As used herein, the term "sulfoxide" is represented by formula A 1 S(O)A 2 wherein A 1 and A 2 can independently be an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or heteroaryl as described herein.

[0082] As used herein, the term "thiol" is represented by the formula -SH.

[0083] The term "polymer" includes polyalkylene, polyether, polyester and other groups having repeating units such as, but not limited to, -(CH 2 O) n -CH 3 、-(CH 2 CH 2 O) n -CH 3 、-[CH 2 CH(CH 3 )] n -CH 3 、-[CH 2 CH(COOCH 3 )] n -CH 3 、-[CH 2 CH(COOCH 2 CH 3 )] n -CH 3 and -[CH 2 CH(COO t Bu)] n -CH 3 , where n is an integer (e.g., n > 1 or n > 2).

[0084] As used herein, "R", "R 1 ", "R 2 ", "R 3 ", "R n " (where n is an integer) can independently include hydrogen or one or more of the groups listed above. For example, if R 1If it is a straight-chain alkyl, one of the hydrogen atoms of the alkyl can optionally be substituted by a hydroxyl group, an alkoxy group, an alkyl group, a halide, etc. Depending on the group selected, the first group can be incorporated into the second group, or alternatively, the first group can be a side group of the second group (i.e., connected to the second group). For example, for the phrase "alkyl including an amino group", the amino group can be incorporated into the main chain of the alkyl. Alternatively, the amino group can be connected to the main chain of the alkyl. The nature of the one or more groups selected will determine whether the first group is embedded in the second group or connected to the second group.

[0085] As used herein, the compounds of the present disclosure can contain "optionally substituted" moieties. Generally, whether or not preceded by the term "optionally", the term "substituted" means that one or more hydrogens of the designated moiety are replaced by a suitable substituent. Unless otherwise indicated, an "optionally substituted" group can have a suitable substituent at each substitutable position of the group, and when more than one position in any given structure can be substituted by more than one substituent selected from the designated group, at each position, the substituents can be the same or different. The combinations of substituents contemplated by the present disclosure are preferably those that result in the formation of stable or chemically viable compounds. It is also contemplated that, in some aspects, unless expressly and oppositely indicated, individual substituents can be further optionally substituted (i.e., further substituted or unsubstituted).

[0086] In some aspects, the structure of the compound can be represented by the following formula:

[0087]

[0088] which is understood to be equivalent to the following formula:

[0089]

[0090] where n is generally an integer. That is, R n should be understood to represent five independent substituents, R n(a) , R n(b) , R n (c) , R n(d) , R n(e) . "Independent substituents" means that each R substituent can be defined independently. For example, if in one case R n(a) is a halogen, then in that case R n(b) is not necessarily a halogen.

[0091] In the chemical structures and moieties disclosed and described herein, for R, R 1 , R 2 , R 3 , R 4 , R 5 , R6 have been cited multiple times. Any description of R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 etc. in this specification applies to any structure or part that separately refers to R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 etc.

[0092] Compound

[0093] The compounds disclosed herein are applicable to a variety of optical and electro - optical devices, including but not limited to light - absorbing devices such as solar and photosensitive devices, organic light - emitting devices (OLEDs), light - emitting devices, or devices that can both absorb and emit light and serve as markers for biological applications.

[0094] The compounds disclosed herein can be used in a variety of applications. As luminescent materials, the compounds can be used in organic light - emitting devices (OLEDs), light - emitting devices, and displays, as well as other light - emitting devices.

[0095] On the other hand, compared with conventional materials, the compounds can provide improved efficiency, improved operating life, or both in lighting devices (e.g., organic light - emitting devices).

[0096] The compounds of the present disclosure can be prepared using a variety of methods, including but not limited to those described in the examples provided herein.

[0097] Compounds of the Invention

[0098] On the one hand, the present invention relates to a compound of general formula I:

[0099]

[0100] Wherein:

[0101] M represents Pt(II) or Pd(II);

[0102] R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each independently is absent or, when valence permits, is present as a single substituent or multiple substituents, and R 1 , R3 , R 4 , R 5 , R 6 and R 8 each independently represents hydrogen, deuterium, halogen, hydroxyl, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof;

[0103] where there are two adjacent substituents R 2 , and the group Y 2 bonded to the group R 4a , Y 4b , Y 4c or Y 4d is each C, and the two adjacent groups R 2 are represented by formula A:

[0104]

[0105] where * represents the bond of general formula I;

[0106] X represents a single bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 , C=O, SiR 7 R 8 , GeR 7 R 8 , NR 7 , PR 7 , PR 7 R 8 , R 7 , P=O, AsR 7 , R 7 As=O, S=O, SO 2 , Se=O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 , Bi=O or BiR 7 , or X is absent, where when X is absent, L 4 is with the group including Z2 There is no bond between the rings;

[0107] X 1 represents a single bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 , C=O, SiR 7 R 8 , GeR 7 R 8 , NR 7 , PR 7 , PR 7 R 8 , R 7 , P=O, AsR 7 , R 7 , As=O, S=O, SO 2 , Se=O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 , Bi=O or BiR 7 ;

[0108] R 7 and R 8 each occurrence of which independently does not exist or, where valency permits, exists in the form of a single substituent or multiple substituents, and each of R 7 and R 8 independently represents hydrogen, deuterium, halogen, hydroxyl, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; or any two of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 represent a covalent bond;

[0109] R 1 , R 2 , R3 , R 4 , R 5 , R 6 , R 7 , R 8 , X, and X 1 Any two of them can form a fused ring together;

[0110] A, B, C, and D each independently represent C, N, O, or S;

[0111] Y 1 and Y 2 each independently represent hydrogen, deuterium, halogen, hydroxy, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxy, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; where Y 1 and Y 2 can optionally form a fused aromatic or heteroaromatic ring together;

[0112] Y 3a , Y 3b , Y 4a , Y 4b , Y 4c , Y 4d , Y 4e , Y 4f , Y 4g , Y 4h each independently represent C or N;

[0113] Z 1 , Z 2 , Z 3 and Z 4 each independently represent C or N;

[0114] L 4 , L 5 and L 6 each independently represent a 5- to 10-membered aryl, heteroaryl, fused aryl, or fused heteroaryl;

[0115] L 5 is present or absent;

[0116] V 1 and V 2 are independently present or absent; where V 1 and V2 Each of which, if present, independently represents a covalent bond, O, S, Se, P═O, As═O, Bi═O, CR 7 R 8 , C═O, SiR 7 R 8 , GeR 7 R 8 , NR 7 , PR 7 , PR 7 R 8 , R 7 , P═O, AsR 7 , R 7 , As═O, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 , Bi═O or BiR 7 ; where when V 1 is absent, then L 4 does not combine with L 5 ; and when V 2 is absent, then L 6 does not combine with L 5 ;

[0117] V 3 is present or absent, where V 3 , if present, represents a covalent bond, C, N, Si, O, S, Ge, P, As, Se, B, Al or Bi, or, if the valence allows, each independently represents CR 7 , SiR 7 , GeR 7 , NR 7 , P═O, As═O, B, BR 7 , AlR 7 , Bi═O, CR 7 R 8 , C═O, SiR 7 R 8 , GeR 7 R 8 , NR 7 , PR 7 , PR 7 R 8 , R 7 , P═O, AsR 7 , R 7As=O, S=O, SO 2 , Se=O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi=O or BiR 7 ; where when V 3 is absent, then Y 2a binds directly to Y 2b ; and

[0118] Each n is independently an integer, subject to valence constraints.

[0119] In one embodiment, two additional adjacent groups R 2 together are represented by formula B:

[0120]

[0121] where X 2 represents a single bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 , C=O, SiR 7 R 8 , GeR 7 R 8 , NR 7 , PR 7 , PR 7 R 8 , R 7 , P=O, AsR 7 , R 7 , As=O, S=O, SO 2 , Se=O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 , Bi=O or BiR 7 ;

[0122] Y 5a , Y 5b , Y 5c , Y 5d each independently represents C or N;

[0123] R 9represents hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazine; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, urea, phosphoramide, silanyl, polymer; or any conjugate or combination thereof; or R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Any two of represent covalent bonds; and

[0124] Each n is independently an integer where valency permits.

[0125] In one embodiment, the compound is represented by Formula II, Formula III, Formula IV, Formula V, Formula VI or Formula VII:

[0126]

[0127]

[0128]

[0129] in:

[0130] Y 1a , Y 1b , Y 1c , Y 1d , Y 2a , Y 2b , Y 3a , Y 3b , Y 4a , Y 4b , Y 4c , Y 4d , Y 4e , Y 4f , Y 4g and Y 4h Each independently represents C or N;

[0131] Z 1 , Z 2 , Z 3 and Z 4 Each independently represents C or N;

[0132] C and D each independently represent C, N, O or S;

[0133] X represents a single bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 、C=O, SiR 7 R 8 、GeR 7 R 8 、NR 7 、PR 7 、PR 7 R 8 、R 7 P=O, AsR 7 、R 7 As=O, S=O, SO 2 、Se=O, SeO 2 、BR 7 、BR 7 R 8 、AlR 7 、AlR 7 R 8 、R 7 Bi=O or BiR 7 ,or X is absent, where when X is absent, there is no bond between L 4 and the ring containing Z 2 ;

[0134] X 1 represents a single bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 、C=O, SiR 7 R 8 、GeR 7 R 8 、NR 7 、PR 7 、PR 7 R 8 、R 7 P=O, AsR 7 、R 7 As=O, S=O, SO 2 、Se=O, SeO 2 、BR 7 、BR 7 R 8 、AlR 7 、AlR 7 R 8 、R 7 Bi=O or BiR 7 ;

[0135] R1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 each independently is absent or, where valence allows, is present as a single substituent or multiple substituents, and R 1 , R 3 , R 4 , R 5 , R 6 and R 7 each independently represents deuterium, halogen, hydroxy, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxy, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; or R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 any two of which represent a covalent bond;

[0136] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , X and X 1 any two of which may together form a fused ring;

[0137] L 4 , L 5 and L 6 each independently represents a 5- to 10-membered aryl, heteroaryl, fused aryl or fused heteroaryl;

[0138] L 5 is present or absent;

[0139] V 1 and V 2 are independently present or absent; where V 1 and V2 Each of which, if present, independently represents a covalent bond, O, S, Se, P═O, As═O, Bi═O, CR 7 R 8 , C═O, SiR 7 R 8 , GeR 7 R 8 , NR 7 , PR 7 , PR 7 R 8 , R 7 , P═O, AsR 7 , R 7 , As═O, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 , Bi═O or BiR 7 ; where when V 1 is absent, then L 4 does not bond with L 5 ; and when V 2 is absent, then L 6 does not bond with L 5 ;

[0140] V 3 is present or absent, where V 3 , if present, represents a covalent bond, C, N, Si, O, S, Ge, P, As, Se, B, Al or Bi, or, if valence allows, each independently represents CR 7 , SiR 7 , GeR 7 , NR 7 , P═O, As═O, B, BR 7 , AlR 7 , Bi═O, CR 7 R 8 , C═O, SiR 7 R 8 , GeR 7 R 8 , NR 7 , PR 7 , PR 7 R 8 , R 7 , P═O, AsR 7 , R 7As=O, S=O, SO 2 , Se=O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 , Bi=O or BiR 7 ; where when V 3 is absent, then Y 2a is directly bonded to Y 2b ; and

[0141] each n is independently an integer, subject to the allowable valences.

[0142] In one embodiment, the compound is represented by General Formula VIII, General Formula IX, General Formula X, General Formula XI, General Formula XII or General Formula XIII:

[0143]

[0144]

[0145]

[0146] where:

[0147] Y 2a , Y 2b , Y 3a , Y 3b , Y 4a , Y 4b , Y 4c , Y 4d , Y 4e , Y 4f , Y 4g and Y 4h each independently represents C or N;

[0148] Z 1 , Z 2 , Z 3 and Z 4 each independently represents C or N;

[0149] A, B, C and D each independently represent C, N, O or S;

[0150] X represents a single bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 , C=O, SiR 7 R 8 , GeR 7 R8 , NR 7 , PR 7 , PR 7 R 8 , R 7 P = O, AsR 7 , R 7 As = O, S = O, SO 2 , Se = O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi = O or BiR 7 , or X does not exist, where when X does not exist, L 4 and the ring including Z 2 has no bond;

[0151] X 1 represents a single bond, O, S, Se, P = O, As = O, Bi = O, CR 7 R 8 , C = O, SiR 7 R 8 , GeR 7 R 8 , NR 7 , PR 7 , PR 7 R 8 , R 7 P = O, AsR 7 , R 7 As = O, S = O, SO 2 , Se = O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi = O or BiR 7 ;

[0152] Y 1 and Y 2Each independently represents hydrogen, deuterium, halogen, hydroxyl, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; wherein Y 1 and Y 2 may optionally together form a fused aromatic or heteroaromatic ring;

[0153] R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 and R 8 each independently is absent or, when valence permits, is present as a single substituent or multiple substituents, and R 1 、R 3 、R 4 、R 5 、R 6 、R 7 and R 8 each independently represents deuterium, halogen, hydroxyl, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; or any two of R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 and R 8 represent a covalent bond;

[0154] R 1 、R 2 、R 3 、R 4 、R 5 、R6 , R 7 , R 8 , X and X 1 Any two of which can together form a fused ring;

[0155] L 4 , L 5 and L 6 each independently represents a 5- to 10-membered aryl, heteroaryl, fused aryl or fused heteroaryl;

[0156] L 5 is present or absent;

[0157] V 1 and V 2 are independently present or absent; where V 1 and V 2 each, if present, independently represents a covalent bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 , C=O, SiR 7 R 8 , GeR 7 R 8 , NR 7 , PR 7 , PR 7 R 8 , R 7 P=O, AsR 7 , R 7 As=O, S=O, SO 2 , Se=O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi=O or BiR 7 ; where when V 1 is absent, then L 4 does not bond with L 5 ; and when V 2 is absent, then L 6 does not bond with L 5 ;

[0158] V 3 is present or absent, where V 3 , if present, represents a covalent bond, C, N, Si, O, S, Ge, P, As, Se, B, Al or Bi, or each independently represents CR 7, SiR 7 , GeR 7 , NR 7 , P=O, As=O, B, BR 7 , AlR 7 , Bi=O, CR 7 R 8 , C=O, SiR 7 R 8 , GeR 7 R 8 , NR 7 , PR 7 , PR 7 R 8 , R 7 , P=O, AsR 7 , R 7 , As=O, S=O, SO 2 , Se=O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 , Bi=O or BiR 7 ; where when V 3 does not exist, then Y 2a directly binds to Y 2b ; and

[0159] In the case where the valence is allowed, each n is independently an integer.

[0160] In one embodiment, the compound is represented by general formula XIV, general formula XV, general formula XVI or general formula XVII:

[0161]

[0162]

[0163] Wherein:

[0164] Y 1a , Y 1b , Y 1c , Y 1d , Y 2a , Y 2b , Y 3a , Y 3b , Y 4e , Y 4f , Y 4g , Y 4h , Y 5a , Y 5b , Y5c and Y 5d each independently represents C or N;

[0165] Z 1 、Z 2 、Z 3 and Z 4 each independently represents C or N;

[0166] C and D each independently represent C, N, O or S;

[0167] X represents a single bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 、C=O, SiR 7 R 8 、GeR 7 R 8 、NR 7 、PR 7 、PR 7 R 8 、R 7 P=O, AsR 7 、R 7 As=O, S=O, SO 2 、Se=O, SeO 2 、BR 7 、BR 7 R 8 、AlR 7 、AlR 7 R 8 、R 7 Bi=O or BiR 7 , or X does not exist, where when X does not exist, L 4 and the ring including Z 2 there is no bond;

[0168] X 1 and X 2 each independently represents a single bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 、C=O, SiR 7 R 8 、GeR 7 R 8 、NR 7 、PR 7 、PR 7 R 8 、R 7 P=O, AsR 7 、R 7 As=O, S=O, SO 2 、Se=O, SeO2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi = O or BiR 7 ;

[0169] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 Each of and R independently does not exist or exists in the form of a single substituent or multiple substituents when the valence allows, and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 Each of and R independently represents hydrogen, deuterium, halogen, hydroxyl, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; or R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 Any two of and R represent a covalent bond;

[0170] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R7 and R 8 and R 9 and R 10 and X, X 1 and X 2 Any two of them can form a fused ring together;

[0171] L 4 and L 5 and L 6 each independently represents a 5- to 10-membered aryl, heteroaryl, fused aryl or fused heteroaryl;

[0172] L 5 is present or absent;

[0173] V 1 and V 2 independently exist or not; where V 1 and V 2 each, if present, independently represents a covalent bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 , C=O, SiR 7 R 8 , GeR 7 R 8 , NR 7 , PR 7 , PR 7 R 8 , R 7 P=O, AsR 7 , R 7 As=O, S=O, SO 2 , Se=O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi=O or BiR 7 ; where when V 1 is absent, then L 4 does not combine with L 5 ; and when V 2 is absent, then L 6 does not combine with L 5 ;

[0174] V 3 is present or absent, where V 3, if present, represents a covalent bond, C, N, Si, O, S, Ge, P, As, Se, B, Al, or Bi, or, if valence permits, each independently represents CR 7 、SiR 7 ,GeR 7 NR 7 、P=O、As=O、B、BR 7 , AlR 7 、Bi=O、CR 7 R 8 、C=O、SiR 7 R 8 ,GeR 7 R 8 NR 7 , PR 7 , PR 7 R 8 , R 7 P=O、AsR 7 , R 7 As=O、S=O、SO 2 、Se=O、SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi=O or BiR 7 ; When V 3 If it does not exist, then Y 2a Directly with Y 2b Combined; and

[0175] Each n is independently an integer where valency permits.

[0176] In one embodiment, the compound is represented by Formula XVIII, Formula XIX, Formula XX or Formula XXI:

[0177]

[0178]

[0179] in:

[0180] Y 2a , Y 2b , Y 3a , Y 3b , Y 4e , Y 4f , Y 4g , Y 4h , Y 5a, Y 5b , Y 5c and Y 5d each independently represents C or N;

[0181] Z 1 , Z 2 , Z 3 and Z 4 each independently represents C or N;

[0182] A, B, C, and D each independently represent C, N, O, or S;

[0183] X represents a single bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 , C=O, SiR 7 R 8 , GeR 7 R 8 , NR 7 , PR 7 , PR 7 R 8 , R 7 P=O, AsR 7 , R 7 As=O, S=O, SO 2 , Se=O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 , Bi=O or BiR 7 , or X does not exist, where when X does not exist, L 4 and the ring including Z 2 has no bond;

[0184] X 1 and X 2 each independently represents a single bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 , C=O, SiR 7 R 8 , GeR 7 R 8 , NR 7 , PR 7 , PR 7 R 8 , R 7 P=O, AsR 7 , R 7 As=O, S=O, SO2 、 Se=O, SeO 2 、 BR 7 、 BR 7 R 8 、 AlR 7 、 AlR 7 R 8 、 R 7 Bi=O or BiR 7 ;

[0185] Y 1 and Y 2 each independently represents hydrogen, deuterium, halogen, hydroxy, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxy, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; wherein Y 1 and Y 2 may optionally together form a fused aromatic or heteroaromatic ring;

[0186] R 1 、 R 2 、 R 3 、 R 4 、 R 5 、 R 6 、 R 7 、 R 8 and R 9 each independently is absent or, where valency permits, is present as a single substituent or multiple substituents, and R 1 、 R 2 、 R 3 、 R 4 、 R 5 、 R 6 、 R 7 、 R 8 and R 9Each of R independently represents hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazine; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, urea, phosphoramide, silanyl, polymer; or any conjugate or combination thereof; or R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Any two of represent a covalent bond;

[0187] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 ,X,X 1 and X 2 Any two of can together form a fused ring;

[0188] L 4 , L 5 and L 6 Each independently represents a 5- to 10-membered aryl group, a heteroaryl group, a condensed aryl group or a condensed heteroaryl group;

[0189] L 5 to exist or not to exist;

[0190] V 1 and V 2 Independently exists or does not exist; where V 1 and V 2 Each of the following, if present, independently represents a covalent bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 、C=O、SiR 7 R 8 ,GeR 7 R 8 NR 7 , PR 7 , PR 7 R8 , R 7 P = O, AsR 7 , R 7 As = O, S = O, SO 2 , Se = O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi = O or BiR 7 ; where when V 1 does not exist, then L 4 does not combine with L 5 ; and when V 2 does not exist, then L 6 does not combine with L 5 ;

[0191] V 3 exists or does not exist, where V 3 if it exists, represents a covalent bond, C, N, Si, O, S, Ge, P, As, Se, B, Al or Bi, or, if the valence allows, each independently represents CR 7 , SiR 7 , GeR 7 , NR 7 , P = O, As = O, B, BR 7 , AlR 7 , Bi = O, CR 7 R 8 , C = O, SiR 7 R 8 , GeR 7 R 8 , NR 7 , PR 7 , PR 7 R 8 , R 7 , P = O, AsR 7 , R 7 , As = O, S = O, SO 2 , Se = O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 Bi = O or BiR 7 ; where when V 3 does not exist, then Y2a Directly combine with Y 2b ; and

[0192] Each n is independently an integer when the valence allows.

[0193] In one embodiment,

[0194]

[0195] Is represented by one of the following structures:

[0196]

[0197]

[0198] Where:

[0199] M represents Pt(II) or Pd(II);

[0200] Y 1a 、Y 1b 、Y 1c 、Y 1d 、Y 3a 、Y 3b 、Y 4e 、Y 4f 、Y 4g 、Y 4h 、Y 5a 、Y 5b 、Y 5c and Y 5d Each independently represents C or N;

[0201] X 1 and X 2 Each independently represents a single bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 、C=O、SiR 7 R 8 、GeR 7 R 8 、NR 7 、PR 7 、PR 7 R 8 、R 7 P=O、AsR 7 、R 7 As=O、S=O、SO 2 、Se=O、SeO 2 、BR 7 、BR 7 R 8 、AlR 7 、AlR7 R 8 、R 7 Bi=O or BiR 7 ;

[0202] R 1 、R 6 、R 7 、R 8 、R 9 and R 10 each independently does not exist or, where valence allows, exists as a single substituent or multiple substituents, and R 1 、R 6 、R 9 and R 10 each independently represents hydrogen, deuterium, halogen, hydroxy, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxy, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, amidosulfonyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; or R 1 、R 6 、R 9 and R 10 any two of which represent a covalent bond;

[0203] R 1 、R 6 、R 9 and R 10 any two of which may together form a fused ring;

[0204] where valence allows, each n independently is an integer.

[0205] In one embodiment,

[0206]

[0207] is represented by one of the following structures:

[0208]

[0209] wherein:

[0210] Y 1a 、Y 1b 、Y 1c 、Y 1d 、Y 2a 、Y 2b 、Y2c , Y 2d , Y 3a , Y 3b and Y 3c each independently represents C or N;

[0211] R 1 , R 2 , R 3 , R 4 , R 5 each of, independently, is absent or, when valency permits, is present in the form of a single substituent or multiple substituents, and R 1 , R 3 , R 4 , R 5 , R 6 and R 7 each independently represents deuterium, halogen, hydroxy, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxy, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof.

[0212] In one embodiment,

[0213]

[0214] is represented by one of the following structures:

[0215]

[0216] wherein:

[0217] Y 1a , Y 1b , Y 1c , Y 1d , Y 1e , Y 1f and Y 1g each independently represents C or N;

[0218] R 1 and R 2 each of, independently, is absent or, when valency permits, is present in the form of a single substituent or multiple substituents, and R 1 and R 2Each of them independently represents deuterium, halogen, hydroxyl, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic group, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; and R 1 and R 2 Any two of them can join together to form a ring;

[0219] Y 1 、Y 2 、Y 3 and Y 4 Each of them independently does not exist or exists, and Y 1 、Y 2 、Y 3 and Y 4 Each of them independently represents hydrogen, deuterium, halogen, hydroxyl, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic group, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; and

[0220] Y 1 、Y 2 、Y 3 and Y 4 Any two of them can join together to form a ring.

[0221] In one embodiment, the compound is selected from the following structures:

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236] Compositions and Devices of the Invention

[0237] The present disclosure also discloses an organic light-emitting diode or a light-emitting device comprising one or more compounds and / or compositions disclosed herein.

[0238] In one aspect, the device is an electro-optic device. The electro-optic device includes, but is not limited to, light-absorbing devices such as solar and photosensitive devices, organic light-emitting devices, light-emitting devices, or devices that can both absorb and emit light and serve as markers for biological applications. For example, the device can be an OLED.

[0239] When a voltage is applied across the device, the OLED utilizes a thin organic film that emits light. The OLED has become an increasingly interesting technology for use in applications such as flat panel displays, lighting, and backlighting. Several OLED materials and configurations are described in U.S. Patent Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety.

[0240] An OLED typically includes at least one organic layer disposed between an anode and a cathode and electrically connected to the anode and the cathode. When a current is applied, the anode injects holes, and the cathode injects electrons into one or more organic layers. The injected holes and electrons each migrate toward the electrode of the opposite charge. When an electron and a hole are localized on the same molecule, an "exciton" is formed as a localized electron-hole pair having an excited energy state. When the exciton relaxes through a light-emission mechanism, light is emitted. In some cases, the exciton can be localized on an excimer or an exciplex. Non-radiative mechanisms such as thermal radiation can also occur, but they are generally considered undesirable.

[0241] The emissive molecules used in initial OLEDs emit light from their singlet state (“fluorescence”), as disclosed, for example, in U.S. Patent No. 4,769,292, which is incorporated herein by reference in its entirety. Fluorescent emission typically occurs within a time frame of less than 10 nanoseconds.

[0242] Recently, OLEDs having emissive materials that emit light from the triplet state (“phosphorescence”) have been demonstrated. Baldo et al., “Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices,” Nature, Vol. 395, 151 - 154, 1998; (“Baldo - I”) and Baldo et al., “Very high - efficiency green organic light - emitting devices based on electrophosphorescence,” Appl. Phys. Lett., Vol. 75, No. 3, 4 - 6 (1999) (“Baldo - II”), which are incorporated herein by reference in their entirety. Phosphorescence is described in more detail at columns 5 - 6 of U.S. Patent No. 7,279,704, which is incorporated by reference.

[0243] One application of phosphorescent emissive molecules is full - color displays. Industry standards for such displays require pixels that are suitable for emitting specific colors (referred to as “saturated” colors). Specifically, these standards require saturated red, green, and blue pixels. Colors can be measured using CIE coordinates well - known in the art. Devices are disclosed herein that include one or more of the compounds or compositions disclosed herein.

[0244] OLEDs can be produced by methods known to those skilled in the art. Generally, OLEDs are produced by continuously vapor - depositing individual layers onto a suitable substrate. Suitable substrates include, for example, glass, inorganic materials such as ITO or IZO, or polymer films. For vapor deposition, conventional techniques such as thermal evaporation, chemical vapor deposition (CVD), physical vapor deposition (PVD), etc. can be used.

[0245] In an alternative process, the organic layer can be coated from a solution or dispersion in a suitable solvent, in which case coating techniques known to those skilled in the art are employed. Suitable coating techniques are, for example, spin coating, casting methods, Langmuir-Blodgett (“LB”) methods, inkjet printing methods, dip coating, relief printing, screen printing, blade coating, slot coating, roller printing, reverse roller printing, offset lithographic printing, flexographic printing, web printing, spraying, coating by brushing or pad printing, etc. Among the methods mentioned, in addition to the above-mentioned vapor deposition, spin coating, inkjet printing methods and casting methods are preferred because these methods are particularly simple and inexpensive to perform. In the case of obtaining the layers of the OLED by spin coating method, casting method or inkjet printing method, a solution prepared by dissolving a composition having a concentration of 0.0001 to 90% by weight in a suitable organic solvent can be used to obtain the coating, and the suitable organic solvents such as benzene, toluene, xylene, tetrahydrofuran, methyltetrahydrofuran, N,N-dimethylformamide, acetone, acetonitrile, anisole, dichloromethane, dimethyl sulfoxide, water and mixtures thereof.

[0246] The compounds described herein can be used in light-emitting devices such as OLEDs. Figure 1 A cross-sectional view of an OLED 100 is depicted. The OLED 100 includes a substrate 102, an anode 104, one or more hole transport materials (HTL) 106, a light processing material 108, one or more electron transport materials (ETL) 110, and a metal cathode layer 112. The anode 104 is typically a transparent material such as indium tin oxide. The light processing material 108 can be an emissive material (EML) comprising an emitter and a host.

[0247] In various aspects, Figure 1 Any of the one or more layers depicted can include indium tin oxide (ITO), poly(3,4-ethylenedioxythiophene) (PEDOT), poly(styrenesulfonate) (PSS), N,N'-di-1-naphthyl-N,N-diphenyl-1,1'-biphenyl-4,4'-diamine (NPD), 1,1-bis((di-4-tolylamino)phenyl)cyclohexane (TAPC), 2,6-bis(N-carbazolyl)pyridine (mCpy), 2,8-bis(diphenylphosphoryl)dibenzothiophene (PO15), LiF, Al, or a combination thereof.

[0248] The light - processing material 108 can comprise one or more compounds of the present disclosure together with an optional host material. The host material can be any suitable host material known in the art. The emission color of the OLED is determined by the emission energy (optical energy gap) of the light - processing material 108, and the emission energy can be adjusted by modulating the electronic structure of the emissive compound, the host material, or both. Both the hole - transporting material in the HTL layer 106 and one or more electron - transporting materials in the ETL layer 110 can comprise any suitable hole - transporter known in the art.

[0249] The compounds described herein can exhibit phosphorescence. Phosphorescent OLEDs (i.e., OLEDs having phosphorescent emitters) generally have higher device efficiency compared to other OLEDs such as fluorescent OLEDs. Light - emitting devices based on electro - phosphorescent emitters are described in more detail in WO2000 / 070655 to Baldo et al., which is hereby incorporated by reference in its teachings regarding OLEDs and specifically phosphorescent OLEDs.

[0250] As contemplated herein, the OLEDs of the present invention can comprise an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer can comprise a host and a phosphorescent dopant. The organic layer can comprise the compounds of the present invention and variants thereof as described herein.

[0251] In some embodiments, the OLED has one or more characteristics selected from the group consisting of flexible, rollable, foldable, stretchable, and bendable. In some embodiments, the OLED is transparent or semi - transparent. In some embodiments, the OLED further includes a layer comprising carbon nanotubes.

[0252] In some embodiments, the OLED further includes a layer comprising a delayed - fluorescence emitter. In some embodiments, the OLED includes an RGB pixel arrangement or a white - plus - color - filter pixel arrangement. In some embodiments, the OLED is a mobile device, a handheld device, or a wearable device. In some embodiments, the OLED is a display panel having a diagonal of less than 10 inches or an area of less than 50 square inches. In some embodiments, the OLED is a display panel having a diagonal of at least 10 inches or an area of at least 50 square inches. In some embodiments, the OLED is a lighting panel.

[0253] In one embodiment, the consumer product is selected from the group consisting of: flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for internal or external illumination and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, mobile phones, tablet computers, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, portable video cameras, viewfinders, microdisplays having a diagonal of less than 2 inches, 3D displays, virtual reality or augmented reality displays, vehicles, video walls including a plurality of displays tiled together, screens for theaters or stadiums, and signs.

[0254] In some embodiments of the emissive region, the emissive region further includes a host, wherein the host includes at least one selected from the group consisting of: metal complexes, benzophenanthrenes, carbazoles, dibenzothiophenes, dibenzofurans, dibenzoselenophenes, azabenzo-phenanthrenes, azacarbazoles, azadibenzothiophenes, azadibenzofurans, and azadibenzoselenophenes.

[0255] The organic layer may also contain a host. In some embodiments, two or more hosts are preferred. In some embodiments, the host used may be: a) a bipolar material; b) an electron transport material; c) a hole transport material; or d) a wide-bandgap material that plays a minor role in charge transport. In some embodiments, the host may contain a metal complex. The host may be a benzophenanthrene containing a benzo-fused thiophene or benzo-fused furan. Any substituent in the host may be an unfused substituent independently selected from the group consisting of: CnH2n+1, OCnH2n+1, OAr1, N(CnH2n+1)2, N(Ar1)(Ar2), CH=CH-CnH2n+1, C≡C-CnH2n+1, Ar1, Ar1-Ar2, and CnH2n-Ar1, or the host has no substituents. In the foregoing substituents, n may range from 1 to 10; and Ar1 and Ar2 may be independently selected from the group consisting of: benzene, biphenyl, naphthalene, benzophenanthrene, carbazole, and their heteroaromatic analogs. The host may be an inorganic compound. For example, an inorganic material containing Zn, such as ZnS.

[0256] Suitable hosts may include, but are not limited to: mCP (1,3-bis(carbazol-9-yl)benzene), mCPy (2,6-bis(N-carbazolyl)pyridine), TCP (1,3,5-tris(carbazol-9-yl)benzene), TCTA (4,4',4”-tris(carbazol-9-yl)triphenylamine), TPBi (1,3,5-tris(1-phenyl-1-H-benzoimidazol-2-yl)benzene), mCBP (3,3-bis(9H-carbazol-9-yl)biphenyl), pCBP (4,4'-bis(carbazol-9-yl)biphenyl), CDBP (4,4'-bis(9-carbazolyl)-2,2'-dimethylbiphenyl), DMFL-CBP (4,4'-bis(carbazol-9-yl)-9,9-dimethylfluorene), FL-4CBP (4,4'-bis(carbazol-9-yl)-9,9-bis(9-phenyl-9H-carbazol)fluorene), FL-2CBP (9,9-bis(4-carbazol-9-yl)phenyl)fluorene (also abbreviated as CPF), DPFL-CBP (4,4'-bis(carbazol-9-yl)-9,9-dimethylxylenylfluorene), FL-2CBP (9,9-bis(9-phenyl-9H-carbazol)fluorene), spiro-CBP (2,2',7,7'-tetrakis(carbazol-9-yl)-9,9'-spirobifluorene), ADN (9,10-bis(naphthalen-2-yl)anthracene), TBADN (3-tert-butyl-9,10-bis(naphthalen-2-yl)anthracene), DPVBi (4,4'-bis(2,2-diphenyleth-1-enyl)-4,4'-dimethylphenyl), p-DMDPVBi (4,4'-bis(2,2-diphenyleth-1-enyl)-4,4'-dimethylphenyl), TDAF (tert(9,9-diarylfluorene)), BSBF (2-(9,9'-spirobifluorene-2-yl)-9,9'-spirobifluorene), TSBF (2,7-bis(9,9'-spirobifluorene-2-yl)-9,9'-spirobifluorene), BDAF (bis(9,9-diarylfluorene)), p-TDPVBi (4,4'-bis(2,2-diphenyleth-1-enyl)-4,4'-di-(tert-butyl)phenyl), TPB3 (1,3,5-tris(pyren-1-yl)benzene, PBD (2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), BP-OXD-Bpy (6,6'-bis[5-(biphenyl-4-yl)-1,3,4-oxadiazol-2-yl]-2,2'-bipyridinyl), NTAZ (4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), Bpy-OXD (1,3-bis[2-(2,2'-bipyridin-6-yl)-1,3,4-oxadiazol-5-yl]benzene), BPhen (4,7-diphenyl-1,10-phenanthroline), TAZ (3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), PADN (2-phenyl-9,10-di(naphthalen-2-yl)anthracene), Bpy-FOXD (2,7-bis[2-(2,2'-bipyridin-6-yl)-1,3,4-oxadiazol-5-yl]-9,9-dimethylfluorene), OXD-7 (1,3-bis[2-(4-tert-butylphenyl)-1,3,4-oxadiazol-5-yl]benzene), HNBphen (2-(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), NBphen (2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), 3TPYMB (tris(2,4,6-trimethyl-3-pyridin-3-yl)phenyl)borane), 2-NPIP (1-methyl-2-(4-(naphthalen-2-yl)phenyl)-1H-imidazo[4,5-f][1,10]phenanthroline), Liq (lithium 8-hydroxyquinolate) and Alq (bis(2-methyl-8-quinolinolato)-4-(phenolato)aluminum) and mixtures of the foregoing substances.,

[0257] The materials described herein that can be used in the specific layers of an organic light-emitting device can be used in combination with a variety of other materials present in the device. For example, the light-emitting dopants disclosed herein can be used in combination with a variety of hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present. The materials described or mentioned below are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.,

[0258] The charge transport layer can be doped with a conductive dopant to substantially change the density of charge carriers in the charge transport layer, which in turn will change the conductivity of the charge transport layer. The conductivity is increased by generating charge carriers in the matrix material, and depending on the type of dopant, a change in the semiconductor Fermi level can also be achieved. The hole transport layer can be doped with a p-type conductive dopant, and an n-type conductive dopant is used in the electron transport layer.,

[0259] Non-limiting examples of conductive dopants that can be used in combination with the materials disclosed herein in an OLED are illustrated below together with the references disclosing these materials: EP01617493, EP01968131, EP2020694, EP2684932, US20050139810, US20070160905, US20090167167, US2010288362, WO06081780, WO 2009003455, WO 2009008277, WO 2009011327, WO 2014009310, US2007252140, US2015060804, US20150123047, and US2012146012.

[0260] The hole injection / transport materials used in the present invention are not particularly limited, and any compound can be used as long as the compound is generally used as a hole injection / transport material. Examples of such materials include, but are not limited to: phthalocyanine or porphyrin derivatives; aromatic amine derivatives; indolocarbazole derivatives; polymers containing fluorohydrocarbons; polymers having a conductive dopant; conductive polymers such as PEDOT / PSS; self-assembled monomers derived from compounds such as phosphonic acid and silane derivatives; metal oxide derivatives such as MoO x ; p-type semiconducting organic compounds such as 1,4,5,8,9,12 - Hexaazatriphenylenehexacarbonitrile; metal complexes and crosslinkable compounds.

[0261] An electron blocking layer (EBL) can be used to reduce the number of electrons and / or excitons leaving the emissive layer. The presence of this blocking layer in a device can result in substantially higher efficiency and / or longer lifetime compared to a similar device lacking a blocking layer. Moreover, the blocking layer can be used to confine emission to a desired region of the OLED. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and / or a higher triplet energy level compared to the emitter closest to the EBL interface. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and / or a higher triplet energy level compared to one or more hosts in the host closest to the EBL interface. In one aspect, the compound used in the EBL contains the same molecule or functional group as the molecule or functional group used in one of the hosts described below.

[0262] The light-emitting layer of the organic EL device of the present invention preferably contains at least a metal complex as a light-emitting material, and may contain a host material using the metal complex as a dopant material. Examples of the host material are not particularly limited, and any metal complex or organic compound can be used as long as the triplet energy level of the host is higher than that of the dopant. As long as the triplet criterion is satisfied, any host material can be used with any dopant.

[0263] One or more additional emitter dopants can be used in combination with the compounds of the present disclosure. Examples of the additional emitter dopants are not particularly limited, and any compound can be used as long as the compound is commonly used as an emitter material. Examples of suitable emitter materials include, but are not limited to, compounds that can emit light through phosphorescence, fluorescence, thermally activated delayed fluorescence (i.e., TADF (also known as E-type delayed fluorescence)), triplet-triplet annihilation, or a combination of these processes.

[0264] A hole blocking layer (HBL) can be used to reduce the number of holes and / or excitons leaving the light-emitting layer. The presence of this blocking layer in the device can result in substantially higher efficiency and / or longer lifetime compared to a similar device lacking the blocking layer. Moreover, the blocking layer can be used to confine emission to a desired region of the OLED. In some embodiments, the HBL material has a lower HOMO (farther from the vacuum level) and / or a higher triplet energy level compared to the emitter closest to the HBL interface. In some embodiments, the HBL material has a lower HOMO (farther from the vacuum level) and / or a higher triplet energy level compared to one or more of the hosts in the host closest to the HBL interface.

[0265] The electron transport layer (ETL) can comprise a material capable of transporting electrons. The electron transport layer can be intrinsic (undoped) or doped. Doping can be used to enhance conductivity. Examples of ETL materials are not particularly limited, and any metal complex or organic compound can be used as long as it is commonly used for transporting electrons.

[0266] In a tandem or stacked OLED, the CGL plays a crucial role in performance and is composed of an n-doped layer and a p-doped layer for injecting electrons and holes, respectively. Electrons and holes are supplied by the CGL and the electrodes. The electrons and holes consumed in the CGL are refilled by the electrons and holes injected from the cathode and anode, respectively; then, the bipolar current gradually reaches a steady state. Typical CGL materials include n- and p-conductive dopants used in the transport layer.

[0267] In any of the above compounds used in each layer of the OLED device, the hydrogen atoms may be partially or fully deuterated. Thus, any specifically listed substituents, such as but not limited to methyl, phenyl, pyridyl, etc., may be in their undeuterated, partially deuterated, and fully deuterated forms. Similarly, the types of substituents, such as but not limited to alkyl, aryl, cycloalkyl, heteroaryl, etc., may also be in their undeuterated, partially deuterated, and fully deuterated forms.

[0268] In yet another aspect of the present disclosure, formulations comprising the novel compounds disclosed herein are described. The formulations may comprise one or more components selected from the group consisting of the following disclosed herein: solvents, hosts, hole injection materials, hole transport materials, and electron transport layer materials.

[0269] Experimental Examples

[0270] The present invention is further described in detail with reference to the following experimental examples. These examples are provided for illustrative purposes only and are not intended to be limiting, unless otherwise stated. Thus, the present invention should in no way be construed as limited to the following examples, but should be construed to cover any and all variations that become apparent as a result of the teachings provided herein.

[0271] Without further description, it is believed that one of ordinary skill in the art can make and utilize the composite materials of the present invention and practice the claimed methods using the foregoing description and the following illustrative examples. Accordingly, the following working examples specifically point out the preferred embodiments of the present invention and should not be construed as limiting the remainder of the disclosure in any way.

[0272] Example 1: Increasing Conjugation During MADF

[0273] The metal-assisted delayed fluorescence (MADF) emission process is capable of harvesting all electro-generated excitons. As Figure 2 shown, when the energy levels of the lowest triplet excited state (T 1 ) and the lowest singlet excited state (S 1 ) are close, triplet excitons can decay radiatively through a combination of intersystem crossing (T 1 →S 1 ) and delayed fluorescence (S 1 →S 0 ) processes. When the energy level of S 1 is made close to the T 1 energy level, the metal-assisted delayed fluorescence process is more efficient.

[0274] The ligands designed according to this scheme focus on 8-base or 2-base ligands. The T 1 energy level remains relatively constant, while the conjugated extension reduces the S 1 energy level ( Figure 3 ).

[0275] In one embodiment, an exemplary compound can be prepared according to the following protocol. Figure 4 The PL data of the compound are presented in

[0276]

[0277] A0 (10 mmol, 1.0 equivalent), B0 (12 mmol, 1.2 equivalents), Pd(dppf)Cl 2 (0.8 mmol, 0.08 equivalent), and K 2 CO 3 (30 mmol, 3.0 equivalents) are added to a dry Schlenk tube equipped with a magnetic stir bar. The tube is evacuated and backfilled with nitrogen. The evacuation and backfilling procedures are repeated a total of three times. Then, the solvent THF / H 2 O (5 / 3, 80 mL) is added under nitrogen protection. The mixture is stirred overnight at reflux in an oil bath and then cooled to ambient temperature. The solvent is removed under reduced pressure, and the residue is purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product C0 in 95% yield.

[0278] C0 (8 mmol, 1.0 equivalent), D0 (8 mmol, 1.0 equivalent), 45 mL of DMF, and 5 mL of distilled water are added to a flask equipped with a magnetic stir bar. The mixture is stirred in an oil bath at 90 °C for 2 days and then cooled to ambient temperature. 200 mL of distilled water is added to the mixture. The system is then filtered and washed with ethyl acetate and acetone to obtain the desired product E0 in 86% yield.

[0279] E0 (1 mmol, 1.0 equivalent), Pd(OAc) 2 (0.1 mmol, 0.1 equivalent), Xphos (0.2 mmol, 0.2 equivalent), K 2 CO 3 (3 mmol, 3.0 equivalents), and 15 mL of DMF are added to a flask equipped with a magnetic stir bar. The flask is evacuated and backfilled with nitrogen. The evacuation and backfilling procedures are repeated a total of three times. The mixture is stirred in an oil bath at 160 °C for 2 days and then cooled to ambient temperature. The solvent is removed under reduced pressure, and the residue is purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product F0 in 43% yield.

[0280] F0 (0.4 mmol, 1.0 equiv) and 6 mL of HOAc and 2 mL of HBr were added to a flask equipped with a magnetic stir bar. The mixture was stirred under reflux in an oil bath for several days and then cooled to ambient temperature. Neutralize the solvent with K 2 CO 3 and then filter and wash with distilled water to obtain the desired product 7-phenyl-7H-benzo[4,5]imidazo[1,2-f]indolo[2,3-c]phenanthridin-2-ol in 95% yield.

[0281] 7-Phenyl-7H-benzo[4,5]imidazo[1,2-f]indolo[2,3-c]phenanthridin-2-ol (1 mmol, 1.0 equiv), 2-(3-bromophenyl)pyridine (1.2 mmol, 1.2 equiv), CuI (0.2 mmol, 0.2 equiv), picolinic acid (0.4 mmol, 0.4 equiv) and K 3 PO 4 (2 mmol, 2.0 equiv) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated three times in total. Then the solvent DMSO (10 mL) was added under nitrogen protection. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed three times with water and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product 3O8-Cz56 in 70% yield.

[0282] 3O8-Cz56 (0.20 mmol, 1.0 equiv), Pd(OAc) 2 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) were added to a dry three-necked flask. Then the flask was subjected to the procedure of evacuation and backfilling with nitrogen three times. The solvent HOAc (10 mL) was added under nitrogen protection. Then the mixture was stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product Pd3O8-Cz56 in 10% to 50% yield.

[0283] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0284]

[0285] 7-phenyl-7H-benzo[4,5]imidazo[1,2-f]indolo[2,3-c]phenanthridin-2-ol (1 mmol, 1.0 equiv), 2-(3-bromophenyl)-4-(tert-butyl)pyridine (1.2 mmol, 1.2 equiv), CuI (0.2 mmol, 0.2 equiv), picolinic acid (0.4 mmol, 0.4 equiv) and K 3 PO 4 (2 mmol, 2.0 equiv) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then solvent DMSO (10 mL) was added under nitrogen protection. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed three times with water and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L1 in a yield of 30% to 70%.

[0286] L1 (0.20 mmol, 1.0 equiv), Pd(OAc) 2 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) were added to a dry three-necked flask. Then the flask was subjected to the procedures of evacuation and backfilling with nitrogen three times. Solvent HOAc (10 mL) was added under nitrogen protection. Then the mixture was stirred in an oil bath under reflux for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC1 in a yield of 10% to 50%.

[0287] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0288]

[0289] 7-phenyl-7H-benzo[4,5]imidazo[1,2-f]indolo[2,3-c]phenanthridin-2-ol (1 mmol, 1.0 equiv), 2-(3-bromo-5-(tert-butyl)phenyl)-4-(tert-butyl)pyridine (1.2 mmol, 1.2 equiv), CuI (0.2 mmol, 0.2 equiv), picolinic acid (0.4 mmol, 0.4 equiv) and K 3 PO 4(2 mmol, 2.0 equiv) was added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then, under nitrogen protection, the solvent DMSO (10 mL) was added. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water three times and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L2 in a yield of 30% to 70%.

[0290] L2 (0.20 mmol, 1.0 equiv), Pd(OAc) 2 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) were added to a dry three-necked flask. Then the flask was subjected to the procedure of evacuation and backfilling with nitrogen three times. Under nitrogen protection, the solvent HOAc (10 mL) was added. Then the mixture was stirred in an oil bath under reflux for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC2 in a yield of 10% to 50%.

[0291] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0292]

[0293] 7-Phenyl-7H-benzo[4,5]imidazo[1,2-f]indolo[2,3-c]phenanthridin-2-ol (1 mmol, 1.0 equiv), 11-bromodibenzo[f,h]quinoline (1.2 mmol, 1.2 equiv), CuI (0.2 mmol, 0.2 equiv), picolinic acid (0.4 mmol, 0.4 equiv) and K 3 PO 4 (2 mmol, 2.0 equiv) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then, under nitrogen protection, the solvent DMSO (10 mL) was added. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water three times and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L3 in a yield of 30% to 70%.

[0294] L3 (0.20 mmol, 1.0 equiv), Pd(OAc) 2 (0.24 mmol, 1.2 equiv) and n-Bu4NBr (0.02 mmol, 0.1 equiv) were added to a dry three-necked flask. The flask was then subjected to a procedure of evacuation and backfilling with nitrogen three times. Solvent HOAc (10 mL) was added under nitrogen protection. The mixture was then stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. The solid was then purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC3 in a yield of 10% to 50%.

[0295] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0296]

[0297] 7-Phenyl-7H-benzo[4,5]imidazo[1,2-f]indolo[2,3-c]phenanthridin-2-ol (1 mmol, 1.0 equiv), 2-bromo-7-phenyl-7H-benzo[4,5]imidazo[1,2-f]indolo[2,3-c]phenanthridine (1.2 mmol, 1.2 equiv), CuI (0.2 mmol, 0.2 equiv), picolinic acid (0.4 mmol, 0.4 equiv) and K 3 PO 4 (2 mmol, 2.0 equiv) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedure was repeated a total of three times. Solvent DMSO (10 mL) was then added under nitrogen protection. The mixture was stirred in an oil bath at a temperature of 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water three times and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L4 in a yield of 30% to 70%.

[0298] L4 (0.20 mmol, 1.0 equiv), Pd(OAc) 2 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) were added to a dry three-necked flask. The flask was then subjected to a procedure of evacuation and backfilling with nitrogen three times. Solvent HOAc (10 mL) was added under nitrogen protection. The mixture was then stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. The solid was then purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC4 in a yield of 10% to 50%.

[0299] In one embodiment, an exemplary compound can be prepared according to the following protocol:

[0300]

[0301] L4 (0.20 mmol, 1.0 equivalent), K 2 PtCl 4 (0.24 mmol, 1.2 equivalents) and n-Bu 4 NBr (0.02 mmol, 0.1 equivalent) were added to a dry three-necked flask. The flask was then subjected to a procedure of evacuation and backfilling with nitrogen three times. Solvent HOAc (10 mL) was added under nitrogen protection. The mixture was then stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. The solid was then purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC5 in a yield of 10% to 50%.

[0302] In one embodiment, an exemplary compound can be prepared according to the following protocol:

[0303]

[0304] 7-Phenyl-7H-benzo[4,5]imidazo[1,2-f]indolo[2,3-c]phenanthridin-2-ol (1 mmol, 1.0 equivalent), 2-bromo-9-(pyridin-2-yl)-9H-carbazole (1.2 mmol, 1.2 equivalents), CuI (0.2 mmol, 0.2 equivalent), picolinic acid (0.4 mmol, 0.4 equivalent) and K 3 PO 4 (2 mmol, 2.0 equivalents) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedure was repeated a total of three times. Then solvent DMSO (10 mL) was added under nitrogen protection. The mixture was stirred in an oil bath at a temperature of 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed three times with water and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L6 in a yield of 30% to 70%.

[0305] L6 (0.20 mmol, 1.0 equivalent), Pd(OAc) 2 (0.24 mmol, 1.2 equivalents) and n-Bu 4NBr (0.02 mmol, 0.1 equiv) was added to a dry three-necked flask. The flask was then subjected to a procedure of evacuation and backfilling with nitrogen three times. The solvent HOAc (10 mL) was added under nitrogen protection. The mixture was then stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. The solid was then purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC6 in a yield of 10% to 50%.

[0306] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0307]

[0308] 7-Phenyl-7H-benzo[4,5]imidazo[1,2-f]indolo[2,3-c]phenanthridin-2-ol (1 mmol, 1.0 equiv), 2-bromo-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1.2 mmol, 1.2 equiv), CuI (0.2 mmol, 0.2 equiv), picolinic acid (0.4 mmol, 0.4 equiv) and K 3 PO 4 (2 mmol, 2.0 equiv) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedure was repeated a total of three times. The solvent DMSO (10 mL) was then added under nitrogen protection. The mixture was stirred in an oil bath at a temperature of 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed three times with water and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L7 in a yield of 30% to 70%.

[0309] L7 (0.20 mmol, 1.0 equiv), Pd(OAc) 2 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) were added to a dry three-necked flask. The flask was then subjected to a procedure of evacuation and backfilling with nitrogen three times. The solvent HOAc (10 mL) was added under nitrogen protection. The mixture was then stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. The solid was then purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC7 in a yield of 10% to 50%.

[0310] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0311]

[0312] 7-phenyl-7H-benzo[4,5]imidazo[1,2-f]indolo[2,3-c]phenanthridin-2-ol (1 mmol, 1.0 equivalent), 2-bromo-6-(tert-butyl)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1.2 mmol, 1.2 equivalents), CuI (0.2 mmol, 0.2 equivalent), picolinic acid (0.4 mmol, 0.4 equivalent) and K 3 PO 4 (2 mmol, 2.0 equivalents) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then the solvent DMSO (10 mL) was added under nitrogen protection. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed three times with water and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L8 in a yield of 30% to 70%.

[0313] L8 (0.20 mmol, 1.0 equivalent), Pd(OAc) 2 (0.24 mmol, 1.2 equivalents) and n-Bu 4 NBr (0.02 mmol, 0.1 equivalent) were added to a dry three-necked flask. Then the flask was subjected to the evacuation and backfilling procedure three times. The solvent HOAc (10 mL) was added under nitrogen protection. Then the mixture was stirred in an oil bath under reflux for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC8 in a yield of 10% to 50%.

[0314] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0315]

[0316] 7-phenyl-7H-benzo[4,5]imidazo[1,2-f]indolo[2,3-c]phenanthridin-2-ol (1 mmol, 1.0 equivalent), 3-bromo-9,9-dimethyl-10-(pyridin-2-yl)-9,10-dihydroacridine (1.2 mmol, 1.2 equivalents), CuI (0.2 mmol, 0.2 equivalent), picolinic acid (0.4 mmol, 0.4 equivalent) and K 3 PO 4(2 mmol, 2.0 equiv) was added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then, under nitrogen protection, the solvent DMSO (10 mL) was added. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water three times and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L9 in a yield of 30% to 70%.

[0317] L9 (0.20 mmol, 1.0 equiv), Pd(OAc) 2 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) were added to a dry three-necked flask. Then the flask was subjected to the procedures of evacuation and backfilling with nitrogen three times. Under nitrogen protection, the solvent HOAc (10 mL) was added. Then the mixture was stirred in an oil bath under reflux for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC9 in a yield of 10% to 50%.

[0318] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0319]

[0320] 7-Phenyl-7H-benzo[4,5]imidazo[1,2-f]indolo[2,3-c]phenanthridin-2-ol (1 mmol, 1.0 equiv), 3-bromo-10-(4-(tert-butyl)pyridin-2-yl)-9,9-dimethyl-9,10-dihydroacridine (1.2 mmol, 1.2 equiv), CuI (0.2 mmol, 0.2 equiv), picolinic acid (0.4 mmol, 0.4 equiv) and K 3 PO 4 (2 mmol, 2.0 equiv) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then, under nitrogen protection, the solvent DMSO (10 mL) was added. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water three times and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L10 in a yield of 30% to 70%.

[0321] Add L10 (0.20 mmol, 1.0 equiv), Pd(OAc) 2 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) to a dry three-necked flask. Then subject the flask to a procedure of evacuation and backfilling with nitrogen three times. Add the solvent HOAc (10 mL) under nitrogen protection. Then stir the mixture in an oil bath under reflux for 3 days and then cool to ambient temperature. Then purify the solid by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC10 in a yield of 10% to 50%.

[0322] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0323]

[0324] Add 7-phenyl-7H-benzo[4,5]imidazo[1,2-f]indolo[2,3-c]phenanthridin-2-ol (1 mmol, 1.0 equiv), 3-bromo-9,9-diphenyl-10-(pyridin-2-yl)-9,10-dihydroacridine (1.2 mmol, 1.2 equiv), CuI (0.2 mmol, 0.2 equiv), picolinic acid (0.4 mmol, 0.4 equiv) and K 3 PO 4 (2 mmol, 2.0 equiv) to a dry Schlenk tube equipped with a magnetic stir bar. Evacuate the tube and backfill with nitrogen. Repeat the evacuation and backfilling procedure a total of three times. Then add the solvent DMSO (10 mL) under nitrogen protection. Stir the mixture in an oil bath at a temperature of 100 °C for 3 days and then cool to ambient temperature and dilute with ethyl acetate. Wash the mixture three times with water and then dry over sodium sulfate and filter. Remove the solvent under reduced pressure and purify the residue by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L11 in a yield of 30% to 70%.

[0325] Add L11 (0.20 mmol, 1.0 equiv), Pd(OAc) 2 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) to a dry three-necked flask. Then subject the flask to a procedure of evacuation and backfilling with nitrogen three times. Add the solvent HOAc (10 mL) under nitrogen protection. Then stir the mixture in an oil bath under reflux for 3 days and then cool to ambient temperature. Then purify the solid by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC11 in a yield of 10% to 50%.

[0326] In one embodiment, an exemplary compound can be prepared according to the following protocol:

[0327]

[0328] 7-Phenyl-7H-benzo[4,5]imidazo[1,2-f]indolo[2,3-c]phenanthridin-2-ol (1 mmol, 1.0 equivalent), 3-bromo-10-(4-(tert-butyl)pyridin-2-yl)-9,9-diphenyl-9,10-dihydroacridine (1.2 mmol, 1.2 equivalents), CuI (0.2 mmol, 0.2 equivalents), picolinic acid (0.4 mmol, 0.4 equivalents) and K 3 PO 4 (2 mmol, 2.0 equivalents) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedure was repeated a total of three times. Then solvent DMSO (10 mL) was added under nitrogen protection. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed three times with water and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L12 in a yield of 30% to 70%.

[0329] L12 (0.20 mmol, 1.0 equivalent), Pd(OAc) 2 (0.24 mmol, 1.2 equivalents) and n-Bu 4 NBr (0.02 mmol, 0.1 equivalent) were added to a dry three-necked flask. Then the flask was subjected to the procedure of evacuation and backfilling with nitrogen three times. Solvent HOAc (10 mL) was added under nitrogen protection. Then the mixture was stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC12 in a yield of 10% to 50%.

[0330] In one embodiment, an exemplary compound can be prepared according to the following protocol:

[0331]

[0332] 7-Phenyl-7H-benzo[4,5]imidazo[1,2-f]indolo[2,3-c]phenanthridin-2-ol (1 mmol, 1.0 equivalent), 11-bromo-8,8-dimethyl-8H-pyrido[3',2':4,5]pyrrolo[3,2,1-de]acridine (1.2 mmol, 1.2 equivalents), CuI (0.2 mmol, 0.2 equivalent), picolinic acid (0.4 mmol, 0.4 equivalent) and K 3 PO 4 (2 mmol, 2.0 equivalents) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then, under nitrogen protection, the solvent DMSO (10 mL) was added. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed three times with water and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L13 in a yield of 30% to 70%.

[0333] L13 (0.20 mmol, 1.0 equivalent), Pd(OAc) 2 (0.24 mmol, 1.2 equivalents) and n-Bu 4 NBr (0.02 mmol, 0.1 equivalent) were added to a dry three-necked flask. Then the flask was subjected to the evacuation and backfilling procedure three times. Under nitrogen protection, the solvent HOAc (10 mL) was added. Then the mixture was stirred in an oil bath under reflux for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC13 in a yield of 10% to 50%.

[0334] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0335]

[0336] 7-Phenyl-7H-benzo[4,5]imidazo[1,2-f]indolo[2,3-c]phenanthridin-2-ol (1 mmol, 1.0 equivalent), 11-bromo-8,8-diphenyl-8H-pyrido[3',2':4,5]pyrrolo[3,2,1-de]acridine (1.2 mmol, 1.2 equivalents), CuI (0.2 mmol, 0.2 equivalent), picolinic acid (0.4 mmol, 0.4 equivalent) and K 3 PO 4(2 mmol, 2.0 equiv) was added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then, under nitrogen protection, the solvent DMSO (10 mL) was added. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water three times and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L14 in a yield of 30% to 70%.

[0337] L14 (0.20 mmol, 1.0 equiv), Pd(OAc) 2 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) were added to a dry three-necked flask. Then the flask was subjected to the procedures of evacuation and backfilling with nitrogen three times. Under nitrogen protection, the solvent HOAc (10 mL) was added. Then the mixture was stirred in an oil bath under reflux for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC14 in a yield of 10% to 50%.

[0338] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0339]

[0340] 7-Phenyl-7H-benzo[4,5]imidazo[1,2-f]indolo[2,3-c]phenanthridin-2-ol (1 mmol, 1.0 equiv), 11-bromo-5,5-dimethyl-5H-[1,8]naphthyrido[3,2,1-jk]carbazole (1.2 mmol, 1.2 equiv), CuI (0.2 mmol, 0.2 equiv), picolinic acid (0.4 mmol, 0.4 equiv) and K 3 PO 4 (2 mmol, 2.0 equiv) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then, under nitrogen protection, the solvent DMSO (10 mL) was added. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water three times and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L15 in a yield of 30% to 70%.

[0341] L15 (0.20 mmol, 1.0 equiv), Pd(OAc) 2 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) were added to a dry three-necked flask. The flask was then subjected to a procedure of evacuation and backfilling with nitrogen three times. The solvent HOAc (10 mL) was added under nitrogen protection. The mixture was then stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. The solid was then purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC15 in a yield of 10% to 50%.

[0342] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0343]

[0344] 7-Phenyl-7H-benzo[4,5]imidazo[1,2-f]indolo[2,3-c]phenanthridin-2-ol (1 mmol, 1.0 equiv), 11-bromo-5,5-diphenyl-5H-[1,8]naphthyrido[3,2,1-jk]carbazole (1.2 mmol, 1.2 equiv), CuI (0.2 mmol, 0.2 equiv), picolinic acid (0.4 mmol, 0.4 equiv) and K 3 PO 4 (2 mmol, 2.0 equiv) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedure was repeated a total of three times. Then the solvent DMSO (10 mL) was added under nitrogen protection. The mixture was stirred in an oil bath at a temperature of 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed three times with water and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L16 in a yield of 30% to 70%.

[0345] L16 (0.20 mmol, 1.0 equiv), Pd(OAc) 2 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) were added to a dry three-necked flask. The flask was then subjected to a procedure of evacuation and backfilling with nitrogen three times. The solvent HOAc (10 mL) was added under nitrogen protection. The mixture was then stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. The solid was then purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC16 in a yield of 10% to 50%.

[0346] In one embodiment, an exemplary compound can be prepared according to the following scheme:

[0347]

[0348] 5,20-Diphenyl-5,20-dihydrobenzo[4,5]imidazo[1,2-f]diindolo[2,3-a:2',3'-c]phenanthridin-8-ol (1 mmol, 1.0 equivalent), 2-(3-bromophenyl)pyridine (1.2 mmol, 1.2 equivalents), CuI (0.2 mmol, 0.2 equivalent), picolinic acid (0.4 mmol, 0.4 equivalent) and K 3 PO 4 (2 mmol, 2.0 equivalents) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then, under nitrogen protection, the solvent DMSO (10 mL) was added. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed three times with water and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L17 in a yield of 30% to 70%.

[0349] L17 (0.20 mmol, 1.0 equivalent), Pd(OAc) 2 (0.24 mmol, 1.2 equivalents) and n-Bu 4 NBr (0.02 mmol, 0.1 equivalent) were added to a dry three-necked flask. Then the flask was subjected to the procedure of evacuation and backfilling with nitrogen three times. Under nitrogen protection, the solvent HOAc (10 mL) was added. Then the mixture was stirred in an oil bath under reflux for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC17 in a yield of 10% to 50%.

[0350] In one embodiment, an exemplary compound can be prepared according to the following scheme:

[0351]

[0352] 5,20 - Diphenyl - 5,20 - dihydrobenzo[4,5]imidazo[1,2 - f]diindolo[2,3 - a:2',3'-c]phenanthridin - 8 - ol (1 mmol, 1.0 equivalent), 8 - bromo - 5,20 - diphenyl - 5,20 - dihydrobenzo[4,5]imidazo[1,2 - f]diindolo[2,3 - a:2',3'-c]phenanthridine (1.2 mmol, 1.2 eq), CuI (0.2 mmol, 0.2 equivalent), picolinic acid (0.4 mmol, 0.4 equivalent) and K 3 PO 4 (2 mmol, 2.0 equivalents) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then, under nitrogen protection, the solvent DMSO (10 mL) was added. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed three times with water and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L18 in a yield of 30% to 70%.

[0353] L18 (0.20 mmol, 1.0 equivalent), Pd(OAc) 2 (0.24 mmol, 1.2 equivalents) and n - Bu 4 NBr (0.02 mmol, 0.1 equivalent) were added to a dry three - necked flask. Then the flask was subjected to the procedure of evacuation and backfilling with nitrogen three times. Under nitrogen protection, the solvent HOAc (10 mL) was added. Then the mixture was stirred in an oil bath under reflux for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC18 in a yield of 10% to 50%.

[0354] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0355]

[0356] L18 (0.20 mmol, 1.0 equivalent), K 2 PtCl 4 (0.24 mmol, 1.2 equivalents) and n - Bu 4NBr (0.02 mmol, 0.1 equivalent) was added to a dry three-necked flask. Then the flask was subjected to a procedure of evacuation and backfilling with nitrogen three times. The solvent HOAc (10 mL) was added under nitrogen protection. Then the mixture was stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC19 with a yield of 10% to 50%.

[0357] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0358]

[0359] 5,20-Diphenyl-5,20-dihydrobenzo[4,5]imidazo[1,2-f]diindolo[2,3-a:2',3'-c]phenanthridin-8-ol (1 mmol, 1.0 equivalent), 11-bromodibenzo[f,h]quinoline (1.2 mmol, 1.2 equivalents), CuI (0.2 mmol, 0.2 equivalent), picolinic acid (0.4 mmol, 0.4 equivalent) and K 3 PO 4 (2 mmol, 2.0 equivalents) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedure was repeated a total of three times. Then the solvent DMSO (10 mL) was added under nitrogen protection. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water three times and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L20 with a yield of 30% to 70%.

[0360] L20 (0.20 mmol, 1.0 equivalent), Pd(OAc) 2 (0.24 mmol, 1.2 equivalents) and n-Bu 4 NBr (0.02 mmol, 0.1 equivalent) were added to a dry three-necked flask. Then the flask was subjected to a procedure of evacuation and backfilling with nitrogen three times. The solvent HOAc (10 mL) was added under nitrogen protection. Then the mixture was stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC20 with a yield of 10% to 50%.

[0361] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0362]

[0363] 5,20 - Diphenyl - 5,20 - dihydrobenzo[4,5]imidazo[1,2 - f]diindolo[2,3 - a:2',3' - c]phenanthridin - 8 - ol (1 mmol, 1.0 equiv), 2 - bromo - 9 - (pyridin - 2 - yl) - 9H - carbazole (1.2 mmol, 1.2 equiv), CuI (0.2 mmol, 0.2 equiv), picolinic acid (0.4 mmol, 0.4 equiv) and K 3 PO 4 (2 mmol, 2.0 equiv) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then, under nitrogen protection, the solvent DMSO (10 mL) was added. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water three times and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L21 in a yield of 30% to 70%.

[0364] L21 (0.20 mmol, 1.0 equiv), Pd(OAc) 2 (0.24 mmol, 1.2 equiv) and n - Bu 4 NBr (0.02 mmol, 0.1 equiv) were added to a dry three - necked flask. Then the flask was subjected to the procedure of evacuation and backfilling with nitrogen three times. Under nitrogen protection, the solvent HOAc (10 mL) was added. Then the mixture was stirred in an oil bath under reflux for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC21 in a yield of 10% to 50%.

[0365] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0366]

[0367] 5,20 - Diphenyl - 5,20 - dihydrobenzo[4,5]imidazo[1,2 - f]diindolo[2,3 - a:2',3' - c]phenanthridin - 8 - ol (1 mmol, 1.0 equiv), 11 - bromo - 5,5 - dimethyl - 5H - [1,8]naphthyrido[3,2,1 - jk]carbazole (1.2 mmol, 1.2 equiv), CuI (0.2 mmol, 0.2 equiv), picolinic acid (0.4 mmol, 0.4 equiv) and K 3 PO 4(2 mmol, 2.0 equiv) was added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then, under nitrogen protection, the solvent DMSO (10 mL) was added. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water three times and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L22 in a yield of 30% to 70%.

[0368] L22 (0.20 mmol, 1.0 equiv), Pd(OAc) 2 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) were added to a dry three-necked flask. Then the flask was subjected to the procedure of evacuation and backfilling with nitrogen three times. Under nitrogen protection, the solvent HOAc (10 mL) was added. Then the mixture was stirred in an oil bath under reflux for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC22 in a yield of 10% to 50%.

[0369] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0370]

[0371] 5,20-Diphenyl-5,20-dihydrobenzo[4,5]imidazo[1,2-f]diindolo[2,3-a:2',3'-c]phenanthridin-8-ol (1 mmol, 1.0 equiv), 3-bromo-9,9-dimethyl-10-(pyridin-2-yl)-9,10-dihydroacridine (1.2 mmol, 1.2 equiv), CuI (0.2 mmol, 0.2 equiv), picolinic acid (0.4 mmol, 0.4 equiv) and K 3 PO 4 (2 mmol, 2.0 equiv) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then, under nitrogen protection, the solvent DMSO (10 mL) was added. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water three times and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L23 in a yield of 30% to 70%.

[0372] L23 (0.20 mmol, 1.0 equiv), Pd(OAc) 2 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) were added to a dry three-necked flask. The flask was then subjected to a procedure of evacuation and backfilling with nitrogen three times. The solvent HOAc (10 mL) was added under nitrogen protection. The mixture was then stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. The solid was then purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC23 in a yield of 10% to 50%.

[0373] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0374]

[0375] 5,20-Diphenyl-5,20-dihydrobenzo[4,5]imidazo[1,2-f]diindolo[2,3-a:2',3'-c]phenanthridin-8-ol (1 mmol, 1.0 equiv), 11-bromo-8,8-dimethyl-8H-pyrido[3',2':4,5]pyrrolo[3,2,1-de]acridine (1.2 mmol, 1.2 equiv), CuI (0.2 mmol, 0.2 equiv), picolinic acid (0.4 mmol, 0.4 equiv) and K 3 PO 4 (2 mmol, 2.0 equiv) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedure was repeated a total of three times. Then the solvent DMSO (10 mL) was added under nitrogen protection. The mixture was stirred in an oil bath at a temperature of 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water three times and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L24 in a yield of 30% to 70%.

[0376] L24 (0.20 mmol, 1.0 equiv), Pd(OAc) 2 (0.24 mmol, 1.2 equiv) and n-Bu 4NBr (0.02 mmol, 0.1 equivalent) was added to a dry three-necked flask. The flask was then subjected to a procedure of evacuation and backfilling with nitrogen three times. The solvent HOAc (10 mL) was added under nitrogen protection. The mixture was then stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. The solid was then purified by silica column chromatography using dichloromethane as the eluent to obtain the desired product MC24 in a yield of 10% to 50%.

[0377] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0378]

[0379] 13-Phenyl-13H-imidazo[1,2-f]indolo[3,2-b]phenanthridin-5-ol (1 mmol, 1.0 equivalent), 2-(3-bromophenyl)pyridine (1.2 mmol, 1.2 equivalents), CuI (0.2 mmol, 0.2 equivalent), picolinic acid (0.4 mmol, 0.4 equivalent) and K 3 PO 4 (2 mmol, 2.0 equivalents) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedure was repeated a total of three times. The solvent DMSO (10 mL) was then added under nitrogen protection. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed three times with water and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L25 in a yield of 30% to 70%.

[0380] L25 (0.20 mmol, 1.0 equivalent), Pd(OAc) 2 (0.24 mmol, 1.2 equivalents) and n-Bu 4 NBr (0.02 mmol, 0.1 equivalent) were added to a dry three-necked flask. The flask was then subjected to a procedure of evacuation and backfilling with nitrogen three times. The solvent HOAc (10 mL) was added under nitrogen protection. The mixture was then stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. The solid was then purified by silica column chromatography using dichloromethane as the eluent to obtain the desired product MC25 in a yield of 10% to 50%.

[0381] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0382]

[0383] L25 (0.20 mmol, 1.0 equiv), K 2 PtCl 4 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) were added to a dry three-necked flask. The flask was then subjected to evacuation and backfilling with nitrogen three times. The solvent HOAc (10 mL) was added under nitrogen protection. The mixture was then stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. The solid was then purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC26 in a yield of 10% to 50%.

[0384] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0385]

[0386] 13-Phenyl-13H-imidazo[1,2-f]indolo[3,2-b]phenanthridin-5-ol (1 mmol, 1.0 equiv), 11-bromoimidazo[1,2-f]phenanthridine (1.2 mmol, 1.2 equiv), CuI (0.2 mmol, 0.2 equiv), picolinic acid (0.4 mmol, 0.4 equiv) and K 3 PO 4 (2 mmol, 2.0 equiv) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. The solvent DMSO (10 mL) was then added under nitrogen protection. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water three times and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L27 in a yield of 30% to 70%.

[0387] L27 (0.20 mmol, 1.0 equiv), Pd(OAc) 2 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) were added to a dry three-necked flask. The flask was then subjected to evacuation and backfilling with nitrogen three times. The solvent HOAc (10 mL) was added under nitrogen protection. The mixture was then stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. The solid was then purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC27 in a yield of 10% to 50%.

[0388] In one embodiment, an exemplary compound can be prepared according to the following protocol:

[0389]

[0390] Add L27 (0.20 mmol, 1.0 equivalent), K 2 PtCl 4 (0.24 mmol, 1.2 equivalents) and n-Bu 4 NBr (0.02 mmol, 0.1 equivalent) to a dry three-necked flask. Then subject the flask to a procedure of evacuation and backfilling with nitrogen three times. Add the HOAc (10 mL) solvent under nitrogen protection. Then stir the mixture in an oil bath under reflux for 3 days, and then cool to ambient temperature. Then purify the solid by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC28 with a yield of 10% to 50%.

[0391] In one embodiment, an exemplary compound can be prepared according to the following protocol:

[0392]

[0393] Add 13-phenyl-13H-imidazo[1,2-f]indolo[3,2-b]phenanthridin-5-ol (1 mmol, 1.0 equivalent), 5-bromo-13-phenyl-13H-imidazo[1,2-f]indolo[3,2-b]phenanthridine (1.2 mmol, 1.2 equivalents), CuI (0.2 mmol, 0.2 equivalent), picolinic acid (0.4 mmol, 0.4 equivalent) and K 3 PO 4 (2 mmol, 2.0 equivalents) to a dry Schlenk tube equipped with a magnetic stir bar. Evacuate the tube and backfill with nitrogen. Repeat the evacuation and backfilling procedure a total of three times. Then add the solvent DMSO (10 mL) under nitrogen protection. Stir the mixture in an oil bath at a temperature of 100 °C for 3 days, and then cool to ambient temperature and dilute with ethyl acetate. Wash the mixture three times with water, and then dry over sodium sulfate and filter. Remove the solvent under reduced pressure, and purify the residue by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L29 with a yield of 30% to 70%.

[0394] Add L29 (0.20 mmol, 1.0 equivalent), Pd(OAc) 2 (0.24 mmol, 1.2 equivalents) and n-Bu 4NBr (0.02 mmol, 0.1 eq) was added to a dry three-necked flask. Then the flask was subjected to a procedure of evacuation and backfilling with nitrogen three times. The solvent HOAc (10 mL) was added under nitrogen protection. Then the mixture was stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC29 with a yield of 10% to 50%.

[0395] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0396]

[0397] L29 (0.20 mmol, 1.0 eq), K 2 PtCl 4 (0.24 mmol, 1.2 eq) and n-Bu 4 NBr (0.02 mmol, 0.1 eq) were added to a dry three-necked flask. Then the flask was subjected to a procedure of evacuation and backfilling with nitrogen three times. The solvent HOAc (10 mL) was added under nitrogen protection. Then the mixture was stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC30 with a yield of 10% to 50%.

[0398] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0399]

[0400] 13-Phenyl-13H-imidazo[1,2-f]indolo[3,2-b]phenanthridin-5-ol (1 mmol, 1.0 eq), 2-bromo-9-(pyridin-2-yl)-9H-carbazole (1.2 mmol, 1.2 eq), CuI (0.2 mmol, 0.2 eq), picolinic acid (0.4 mmol, 0.4 eq) and K 3 PO 4 (2 mmol, 2.0 eq) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedure was repeated a total of three times. Then the solvent DMSO (10 mL) was added under nitrogen protection. The mixture was stirred in an oil bath at a temperature of 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water three times and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L31 with a yield of 30% to 70%.

[0401] Add L31 (0.20 mmol, 1.0 equiv), Pd(OAc) 2 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) to a dry three-necked flask. Then subject the flask to a procedure of evacuation and backfilling with nitrogen three times. Add the HOAc (10 mL) solvent under nitrogen protection. Then stir the mixture under reflux in an oil bath for 3 days and then cool to ambient temperature. Then purify the solid by silica column chromatography using dichloromethane as the eluent to obtain the desired product MC31 in a yield of 10% to 50%.

[0402] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0403]

[0404] Add L31 (0.20 mmol, 1.0 equiv), K 2 PtCl 4 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) to a dry three-necked flask. Then subject the flask to a procedure of evacuation and backfilling with nitrogen three times. Add the HOAc (10 mL) solvent under nitrogen protection. Then stir the mixture under reflux in an oil bath for 3 days and then cool to ambient temperature. Then purify the solid by silica column chromatography using dichloromethane as the eluent to obtain the desired product MC32 in a yield of 10% to 50%.

[0405] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0406]

[0407] Add 13-phenyl-13H-imidazo[1,2-f]indolo[3,2-b]phenanthridin-5-ol (1 mmol, 1.0 equiv), 11-bromo-5,5-dimethyl-5H-[1,8]naphthyrido[3,2,1-jk]carbazole (1.2 mmol, 1.2 equiv), CuI (0.2 mmol, 0.2 equiv), picolinic acid (0.4 mmol, 0.4 equiv) and K 3 PO 4(2 mmol, 2.0 equiv) was added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then, the solvent DMSO (10 mL) was added under nitrogen protection. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water three times and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L33 with a yield of 30% to 70%.

[0408] L33 (0.20 mmol, 1.0 equiv), Pd(OAc) 2 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) were added to a dry three-necked flask. Then, the flask was subjected to the evacuation and backfilling procedure three times. The solvent HOAc (10 mL) was added under nitrogen protection. Then, the mixture was stirred in an oil bath under reflux for 3 days and then cooled to ambient temperature. Then, the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC34 with a yield of 10% to 50%.

[0409] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0410]

[0411] L33 (0.20 mmol, 1.0 equiv), K 2 PtCl 4 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) were added to a dry three-necked flask. Then, the flask was subjected to the evacuation and backfilling procedure three times. The solvent HOAc (10 mL) was added under nitrogen protection. Then, the mixture was stirred in an oil bath under reflux for 3 days and then cooled to ambient temperature. Then, the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC34 with a yield of 10% to 50%.

[0412] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0413]

[0414] 13-Phenyl-13H-imidazo[1,2-f]indolo[3,2-b]phenanthridin-5-ol (1 mmol, 1.0 equiv), 3-bromo-9,9-dimethyl-10-(pyridin-2-yl)-9,10-dihydroacridine (1.2 mmol, 1.2 equiv), CuI (0.2 mmol, 0.2 equiv), picolinic acid (0.4 mmol, 0.4 equiv) and K 3 PO 4 (2 mmol, 2.0 equiv) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then the solvent DMSO (10 mL) was added under nitrogen protection. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed three times with water and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L35 in a yield of 30% to 70%.

[0415] L35 (0.20 mmol, 1.0 equiv), Pd(OAc) 2 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) were added to a dry three-necked flask. Then the flask was subjected to the evacuation and backfilling procedure three times. The solvent HOAc (10 mL) was added under nitrogen protection. Then the mixture was stirred in an oil bath under reflux for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC35 in a yield of 10% to 50%.

[0416] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0417]

[0418] L35 (0.20 mmol, 1.0 equiv), K 2 PtCl 4 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) were added to a dry three-necked flask. Then the flask was subjected to the evacuation and backfilling procedure three times. The solvent HOAc (10 mL) was added under nitrogen protection. Then the mixture was stirred in an oil bath under reflux for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC36 in a yield of 10% to 50%.

[0419] In one embodiment, an exemplary compound can be prepared according to the following protocol:

[0420]

[0421] 13-Phenyl-13H-imidazo[1,2-f]indolo[3,2-b]phenanthridin-5-ol (1 mmol, 1.0 equivalent), 11-bromo-8,8-dimethyl-8H-pyrido[3',2':4,5]pyrrolo[3,2,1-de]acridine (1.2 mmol, 1.2 equivalents), CuI (0.2 mmol, 0.2 equivalent), picolinic acid (0.4 mmol, 0.4 equivalent), and K 3 PO 4 (2 mmol, 2.0 equivalents) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then, the solvent DMSO (10 mL) was added under nitrogen protection. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed three times with water and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L37 in a yield of 30% to 70%.

[0422] L37 (0.20 mmol, 1.0 equivalent), Pd(OAc) 2 (0.24 mmol, 1.2 equivalents), and n-Bu 4 NBr (0.02 mmol, 0.1 equivalent) were added to a dry three-necked flask. Then, the flask was subjected to the evacuation and backfilling procedure three times. The solvent HOAc (10 mL) was added under nitrogen protection. Then, the mixture was stirred in an oil bath under reflux for 3 days and then cooled to ambient temperature. Then, the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC37 in a yield of 10% to 50%.

[0423] In one embodiment, an exemplary compound can be prepared according to the following protocol:

[0424]

[0425] L37 (0.20 mmol, 1.0 equivalent), K 2 PtCl 4 (0.24 mmol, 1.2 equivalents), and n-Bu 4NBr (0.02 mmol, 0.1 equivalent) was added to a dry three-necked flask. Then the flask was subjected to a procedure of evacuation and backfilling with nitrogen three times. The solvent HOAc (10 mL) was added under nitrogen protection. Then the mixture was stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC38 with a yield of 10% to 50%.

[0426] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0427]

[0428] 7-Phenyl-7H-imidazo[1,2-f]indolo[2,3-c]phenanthridin-2-ol (1 mmol, 1.0 equivalent), 2-(3-bromophenyl)pyridine (1.2 mmol, 1.2 equivalents), CuI (0.2 mmol, 0.2 equivalent), picolinic acid (0.4 mmol, 0.4 equivalent) and K 3 PO 4 (2 mmol, 2.0 equivalents) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedure was repeated a total of three times. Then the solvent DMSO (10 mL) was added under nitrogen protection. The mixture was stirred in an oil bath at a temperature of 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water three times and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L39 with a yield of 30% to 70%.

[0429] L39 (0.20 mmol, 1.0 equivalent), Pd(OAc) 2 (0.24 mmol, 1.2 equivalents) and n-Bu 4 NBr (0.02 mmol, 0.1 equivalent) were added to a dry three-necked flask. Then the flask was subjected to a procedure of evacuation and backfilling with nitrogen three times. The solvent HOAc (10 mL) was added under nitrogen protection. Then the mixture was stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC39 with a yield of 10% to 50%.

[0430] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0431]

[0432] 7-Phenyl-7H-imidazo[1,2-f]indolo[2,3-c]phenanthridin-2-ol (1 mmol, 1.0 equiv), 2-bromo-9-(pyridin-2-yl)-9H-carbazole (1.2 mmol, 1.2 equiv), CuI (0.2 mmol, 0.2 equiv), picolinic acid (0.4 mmol, 0.4 equiv) and K 3 PO 4 (2 mmol, 2.0 equiv) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then, under nitrogen protection, the solvent DMSO (10 mL) was added. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed three times with water and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product ON2-Cz56 in a yield of 30% to 70%.

[0433] ON2-Cz56 (0.20 mmol, 1.0 equiv), Pd(OAc) 2 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) were added to a dry three-necked flask. Then the flask was subjected to the procedure of evacuation and backfilling with nitrogen three times. Under nitrogen protection, the solvent HOAc (10 mL) was added. Then the mixture was stirred in an oil bath under reflux for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product PdON2-CZ56 in a yield of 10% to 50%.

[0434] In one embodiment, exemplary compounds can be prepared according to the following scheme. In Figure 5 the photoluminescence spectra of this compound are presented.

[0435]

[0436] ON2-CZ56 (0.20 mmol, 1.0 equiv), K 2 PtCl 4 (0.24 mmol, 1.2 equiv) and n-Bu 4NBr (0.02 mmol, 0.1 equivalent) was added to a dry three-necked flask. Then the flask was subjected to evacuation and backfilling with nitrogen three times. The solvent HOAc (10 mL) was added under nitrogen protection. Then the mixture was stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product PtON2-CZ56 in a yield of 10% to 50%.

[0437] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0438]

[0439] 7-Phenyl-7H-imidazo[1,2-f]indolo[2,3-c]phenanthridin-2-ol (1 mmol, 1.0 equivalent), 2-bromo-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1.2 mmol, 1.2 equivalents), CuI (0.2 mmol, 0.2 equivalent), picolinic acid (0.4 mmol, 0.4 equivalent) and K 3 PO 4 (2 mmol, 2.0 equivalents) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then the solvent DMSO (10 mL) was added under nitrogen protection. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water three times and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product ON2-Cz56-tbu in a yield of 30% to 70%.

[0440] ON2-Cz56-tbu (0.20 mmol, 1.0 equivalent), K 2 PtCl 4 (0.24 mmol, 1.2 equivalents) and n-Bu 4 NBr (0.02 mmol, 0.1 equivalent) were added to a dry three-necked flask. Then the flask was subjected to evacuation and backfilling with nitrogen three times. The solvent HOAc (10 mL) was added under nitrogen protection. Then the mixture was stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product PtON2-CZ56-tbu in a yield of 10% to 50%.

[0441] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0442]

[0443] Benzimidazo[4,5]imidazo[1,2-f]benzo[4,5]thieno[2,3-c]phenanthridin-2-ol (1 mmol, 1.0 equiv), 2-(3-bromophenyl)pyridine (1.2 mmol, 1.2 equiv), CuI (0.2 mmol, 0.2 equiv), picolinic acid (0.4 mmol, 0.4 equiv) and K 3 PO 4 (2 mmol, 2.0 equiv) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then, under nitrogen protection, the solvent DMSO (10 mL) was added. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed three times with water and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L40 in a yield of 56%.

[0444] L40 (0.20 mmol, 1.0 equiv), K 2 PtCl 4 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) were added to a dry three-necked flask. Then the flask was subjected to the procedure of evacuation and backfilling with nitrogen three times. Under nitrogen protection, the solvent HOAc (10 mL) was added. Then the mixture was stirred in an oil bath under reflux for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC40 in a yield of 59%.

[0445] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0446]

[0447] Benzimidazo[4,5]imidazo[1,2-f]benzo[4,5]thieno[2,3-c]phenanthridin-2-ol (1 mmol, 1.0 equiv), 2-(3-bromophenyl)-4-(tert-butyl)pyridine (1.2 mmol, 1.2 equiv), CuI (0.2 mmol, 0.2 equiv), picolinic acid (0.4 mmol, 0.4 equiv) and K 3 PO 4(2 mmol, 2.0 equiv) was added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then, under nitrogen protection, the solvent DMSO (10 mL) was added. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water three times and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L41 with a yield of 30% to 70%.

[0448] L41 (0.20 mmol, 1.0 equiv), K 2 PtCl 4 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) were added to a dry three-necked flask. Then the flask was subjected to the procedure of evacuation and backfilling with nitrogen three times. Under nitrogen protection, the solvent HOAc (10 mL) was added. Then the mixture was stirred in an oil bath under reflux for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC41 with a yield of 10% to 50%.

[0449] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0450]

[0451] Benzo[4,5]imidazo[1,2-f]benzo[4,5]thieno[2,3-c]phenanthridin-2-ol (1 mmol, 1.0 equiv), 2-bromobenzo[4,5]imidazo[1,2-f]benzo[4,5]thieno[2,3-c]phenanthridine (1.2 mmol, 1.2 equiv), CuI (0.2 mmol, 0.2 equiv), picolinic acid (0.4 mmol, 0.4 equiv) and K 3 PO 4 (2 mmol, 2.0 equiv) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then, under nitrogen protection, the solvent DMSO (10 mL) was added. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water three times and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L42 with a yield of 30% to 70%.

[0452] L42 (0.20 mmol, 1.0 equivalent), K 2 PtCl 4 (0.24 mmol, 1.2 equivalents) and n-Bu 4 NBr (0.02 mmol, 0.1 equivalent) were added to a dry three-necked flask. The flask was then subjected to a procedure of evacuation and backfilling with nitrogen three times. The solvent HOAc (10 mL) was added under nitrogen protection. The mixture was then stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. The solid was then purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC42 in a yield of 10% to 50%.

[0453] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0454]

[0455] L42 (0.20 mmol, 1.0 equivalent), K 2 PtCl 4 (0.24 mmol, 1.2 equivalents) and n-Bu 4 NBr (0.02 mmol, 0.1 equivalent) were added to a dry three-necked flask. The flask was then subjected to a procedure of evacuation and backfilling with nitrogen three times. The solvent HOAc (10 mL) was added under nitrogen protection. The mixture was then stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. The solid was then purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC43 in a yield of 10% to 50%.

[0456] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0457]

[0458] Benzo[4,5]thieno[2,3-c]imidazo[1,2-f]phenanthridin-2-ol (1 mmol, 1.0 equivalent), 2-bromo-9-(pyridin-2-yl)-9H-carbazole (1.2 mmol, 1.2 equivalents), CuI (0.2 mmol, 0.2 equivalent), picolinic acid (0.4 mmol, 0.4 equivalent) and K 3 PO 4(2 mmol, 2.0 equiv) was added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then, under nitrogen protection, the solvent DMSO (10 mL) was added. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water three times and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product L44 in a yield of 30% to 70%.

[0459] L44 (0.20 mmol, 1.0 equiv), K 2 PtCl 4 (0.24 mmol, 1.2 equiv) and n-Bu 4 NBr (0.02 mmol, 0.1 equiv) were added to a dry three-necked flask. Then the flask was subjected to the procedure of evacuation and backfilling with nitrogen three times. Under nitrogen protection, the solvent HOAc (10 mL) was added. Then the mixture was stirred in an oil bath under reflux for 3 days and then cooled to ambient temperature. Then the solid was purified by silica gel column chromatography using dichloromethane as the eluent to obtain the desired product MC44 in a yield of 10% to 50%.

[0460] In one embodiment, exemplary compounds can be prepared according to the following scheme:

[0461]

[0462] Benzo[4,5]thieno[2,3-c]imidazo[1,2-f]phenanthridin-2-ol (1 mmol, 1.0 equiv), 2-bromo-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1.2 mmol, 1.2 equiv), CuI (0.2 mmol, 0.2 equiv), picolinic acid (0.4 mmol, 0.4 equiv) and K 3 PO 4 (2 mmol, 2.0 equiv) were added to a dry Schlenk tube equipped with a magnetic stir bar. The tube was evacuated and backfilled with nitrogen. The evacuation and backfilling procedures were repeated a total of three times. Then, under nitrogen protection, the solvent DMSO (10 mL) was added. The mixture was stirred in an oil bath at 100 °C for 3 days and then cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water three times and then dried over sodium sulfate and filtered. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain the desired product ON2-Sz56-tbu in a yield of 30% to 70%.

[0463] ON2-Sz56-tbu (0.20 mmol, 1.0 equivalent), K 2 PtCl 4 (0.24 mmol, 1.2 equivalents) and n-Bu 4 NBr (0.02 mmol, 0.1 equivalent) were added to a dry three-necked flask. The flask was then subjected to a procedure of evacuation and backfilling with nitrogen three times. The solvent HOAc (10 mL) was added under nitrogen protection. The mixture was then stirred under reflux in an oil bath for 3 days and then cooled to ambient temperature. The solid was then purified by silica column chromatography using dichloromethane as the eluent to obtain the desired product PtON2-Sz56-tbu with a yield of 10% to 50%.

[0464] The disclosures of each and every patent, patent application, and publication cited herein are hereby incorporated by reference in their entirety. Although the invention has been disclosed with reference to specific embodiments, it will be apparent to other skilled persons in the art that other embodiments and variations of the invention may be devised without departing from the true spirit and scope of the invention. The appended claims are intended to be construed to include all such embodiments and equivalent variations.

Claims

1. A compound of general formula I Wherein: M represents Pt(II) or Pd(II); R 1 、R 3 、R 4 、R 5 and R 6 each independently is absent or, where valence allows, is present as a single substituent or multiple substituents, and R 1 、R 3 、R 4 、R 5 、R 6 and R 8 each independently represents hydrogen, deuterium, halogen, hydroxy, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxy, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; R 2 present in the form of multiple substituents where valency allows; There are two adjacent substituents R 2 , the group Y 2 combined with the group R 4a , Y 4b , Y 4c or Y 4d is C respectively, and the two adjacent groups R 2 are represented by formula A: Where * represents the bond of general formula I; X represents a single bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 、C=O、SiR 7 R 8 、GeR 7 R 8 、 NR 7 、PR 7 、PR 7 R 8 、R 7 P=O, AsR 7 、R 7 As=O, S=O, SO 2 、Se=O, SeO 2 、BR 7 、BR 7 R 8 、AlR 7 、AlR 7 R 8 、R 7 Bi=O or BiR 7 , or X is absent, where when X is absent, there is no bond between L 4 and the ring containing Z 2 . X 1 represents a single bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 , C=O, SiR 7 R 8 , GeR 7 R 8 , NR 7 、PR 7 、PR 7 R 8 、R 7 P=O, AsR 7 、R 7 As=O, S=O, SO 2 、Se=O, SeO 2 、BR 7 、BR 7 R 8 、AlR 7 、AlR 7 R 8 、R 7 Bi=O or BiR 7 ; R 7 and R 8 each occurrence of which independently is absent or, where valence permits, is present in the form of a single substituent or multiple substituents, and R 7 and R 8 each independently represents hydrogen, deuterium, halogen, hydroxy, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxy, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; or R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 and R 8 any two of which represent a covalent bond; R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、X and X 1 Any two of them can together form a fused ring; A, B, C and D each independently represent C, N, O or S; Y 1 and Y 2 each independently represents hydrogen, deuterium, halogen, hydroxy, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxy, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; provided that Y 1 and Y 2 may optionally together form a fused aromatic or heteroaromatic ring; Y 3a 、Y 3b 、Y 4a 、Y 4b 、Y 4c 、Y 4d 、Y 4e 、Y 4f 、Y 4g 、Y 4h each independently represents C or N; Z 1 , Z 2 , Z 3 and Z 4 Each independently represents C or N; L 4 、L 5 and L 6 each independently represents a C5-C10 aryl, heteroaryl, fused aryl or fused heteroaryl; L 5 Present or absent; V 1 and V 2 may independently be present or absent; wherein each of V 1 and V 2 , if present, independently represents a covalent bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 , C=O, SiR 7 R 8 , GeR 7 R 8 , NR 7 、PR 7 、PR 7 R 8 、R 7 P=O, AsR 7 、R 7 As=O, S=O, SO 2 、Se=O, SeO 2 、BR 7 、BR 7 R 8 、 AlR 7 、AlR 7 R 8 、R 7 Bi = O or BiR 7 ; where when V 1 does not exist, then L 4 does not combine with L 5 ; and When V 2 is absent, then L 6 does not combine with L 5 ; V 3 is present or absent, wherein V 3 if present, represents a covalent bond, C, N, Si, O, S, Ge, P, As, Se, B, Al or Bi, or, if valency permits, independently represents CR 7 , SiR 7 , GeR 7 、NR 7 、P=O, As=O, B, BR 7 、AlR 7 、Bi=O, CR 7 R 8 、C=O, SiR 7 R 8 、GeR 7 R 8 、 NR 7 、PR 7 、PR 7 R 8 、R 7 P=O, AsR 7 、R 7 As=O, S=O, SO 2 、Se=O, SeO 2 、BR 7 、BR 7 R 8 、 AlR 7 、AlR 7 R 8 、R 7 Bi = O or BiR 7 ; where when V 3 does not exist, then Y 2a directly combines with Y 2b ; and Each n is independently an integer, subject to valence requirements.

2. The compound according to claim 1, wherein the two further adjacent groups R 2 together are represented by formula B: wherein X 2 represents a single bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 、C=O, SiR 7 R 8 、GeR 7 R 8 、 NR 7 、PR 7 、PR 7 R 8 、R 7 P=O, AsR 7 、R 7 As=O, S=O, SO 2 、Se=O, SeO 2 、BR 7 、BR 7 R 8 、 AlR 7 、AlR 7 R 8 、R 7 Bi = O or BiR 7 ; Y 5a 、Y 5b 、Y 5c 、Y 5d each independently represents C or N; R 9 represents hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazine; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, urea, phosphoramide, silanyl, polymer; or any conjugate or combination thereof; or R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 Any two of represent covalent bonds; and Each n is independently an integer, subject to valence requirements.

3. The compound according to claim 1, wherein the compound is represented by general formula II, general formula III, general formula IV, general formula V, general formula VI or general formula VII: Wherein: Y 1a 、Y 1b 、Y 1c 、Y 1d 、Y 2a 、Y 2b 、Y 3a 、Y 3b 、Y 4a 、Y 4b 、Y 4c 、Y 4d 、Y 4e 、Y 4f 、Y 4g and Y 4h each independently represents C or N; Z 1 , Z 2 , Z 3 and Z 4 Each independently represents C or N; C and D each independently represent C, N, O or S; X represents a single bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 、C=O、SiR 7 R 8 、GeR 7 R 8 、 NR 7 、PR 7 、PR 7 R 8 、R 7 P=O, AsR 7 、R 7 As=O, S=O, SO 2 、Se=O, SeO 2 、BR 7 、BR 7 R 8 、AlR 7 、AlR 7 R 8 、R 7 Bi=O or BiR 7 ,or X does not exist, where when X does not exist, L 4 has no bond with the ring including Z 2 ; X 1 represents a single bond, O, S, Se, P═O, As═O, Bi═O, CR 7 R 8 , C═O, SiR 7 R 8 , GeR 7 R 8 , NR 7 、PR 7 、PR 7 R 8 、R 7 P=O, AsR 7 、R 7 As=O, S=O, SO 2 、Se=O, SeO 2 、BR 7 、BR 7 R 8 、AlR 7 、AlR 7 R 8 、R 7 Bi=O or BiR 7 ; R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 and R 8 each independently is absent or, where valence allows, is present in the form of a single substituent or multiple substituents, and R 1 、R 3 、R 4 、R 5 、R 6 and R 7 each independently represents deuterium, halogen, hydroxy, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxy, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; or R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 and R 8 any two of which represent a covalent bond; R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、X and X 1 Any two of them can form a fused ring together; L 4 、L 5 and L 6 each independently represents a C5-C10 aryl, heteroaryl, fused aryl or fused heteroaryl; L 5 Present or absent; V 1 and V 2 may independently be present or absent; wherein each of V 1 and V 2 , if present, independently represents a covalent bond, O, S, Se, P═O, As═O, Bi═O, CR 7 R 8 , C═O, SiR 7 R 8 , GeR 7 R 8 , NR 7 , PR 7 , PR 7 R 8 , R 7 P═O, AsR 7 , R 7 , As═O, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 , Bi═O or BiR 7 ; wherein when V 1 is absent, then L 4 is not combined with L 5 ; and When V 2 does not exist, then L 6 is not combined with L 5 ; V 3 is present or absent, where V 3 if present, represents a covalent bond, C, N, Si, O, S, Ge, P, As, Se, B, Al or Bi, or, if valency permits, independently represents CR 7 、SiR 7 、 GeR 7 、NR 7 、P=O、As=O、B、BR 7 、AlR 7 、Bi=O、CR 7 R 8 、C=O、SiR 7 R 8 、GeR 7 R 8 、 NR 7 、PR 7 、PR 7 R 8 、R 7 P=O, AsR 7 、R 7 As=O, S=O, SO 2 、Se=O, SeO 2 、BR 7 、BR 7 R 8 、 AlR 7 、AlR 7 R 8 、R 7 Bi = O or BiR 7 ; where when V 3 does not exist, then Y 2a directly combines with Y 2b ; and Each n is independently an integer, subject to valence requirements.

4. The compound according to claim 1, wherein the compound is represented by general formula VIII, general formula IX, general formula X, general formula XI, general formula XII or general formula XIII: Wherein: Y 2a 、Y 2b 、Y 3a 、Y 3b 、Y 4a 、Y 4b 、Y 4c 、Y 4d 、Y 4e 、Y 4f 、Y 4g and Y 4h each independently represents C or N; Z 1 , Z 2 , Z 3 and Z 4 Each independently represents C or N; A, B, C and D each independently represent C, N, O or S; X represents a single bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 、C=O、SiR 7 R 8 、GeR 7 R 8 、 NR 7 、PR 7 、PR 7 R 8 、R 7 P=O, AsR 7 、R 7 As=O, S=O, SO 2 、Se=O, SeO 2 、BR 7 、BR 7 R 8 、AlR 7 、AlR 7 R 8 、R 7 Bi=O or BiR 7 , or X is absent, where when X is absent, L 4 has no bond with the ring including Z 2 . X 1 represents a single bond, O, S, Se, P═O, As═O, Bi═O, CR 7 R 8 , C═O, SiR 7 R 8 , GeR 7 R 8 , NR 7 、PR 7 、PR 7 R 8 、R 7 P=O, AsR 7 、R 7 As=O, S=O, SO 2 、Se=O, SeO 2 、BR 7 、BR 7 R 8 、AlR 7 、AlR 7 R 8 、R 7 Bi=O or BiR 7 ; Y 1 and Y 2 each independently represents hydrogen, deuterium, halogen, hydroxyl, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic group, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; wherein Y 1 and Y 2 may optionally together form a fused aromatic or heteroaromatic ring; R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 and R 8 each independently is absent or, where valency permits, is present as a single substituent or as multiple substituents, and R 1 、R 3 、R 4 、R 5 、R 6 、R 7 and R 8 each independently represents deuterium, a halogen, a hydroxyl group, a mercapto group, a nitro group, a cyano group, a nitrile, an isonitrile, a sulfinyl group, a sulfhydryl group, a sulfo group, a carboxyl group, a hydrazino group; substituted or unsubstituted: an aryl group, a cycloalkyl group, a cycloalkenyl group, a heterocyclic group, a heteroaryl group, an alkyl group, an alkenyl group, an alkynyl group, an amino group, a monoalkylamino group, a dialkylamino group, a monoarylamino group, a diarylamino group, an alkoxy group, an aryloxy group, a haloalkyl group, an aralkyl group, an ester, an alkoxycarbonyl group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a ureido group, a phosphoramide, a silyl group, a polymer; or any conjugate or combination thereof; or R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 and R 8 any two of which represent a covalent bond; R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、X and X 1 Any two of them can together form a fused ring; L 4 、L 5 and L 6 each independently represents a 5- to 10-membered aryl, heteroaryl, fused aryl or fused heteroaryl; L 5 Present or absent; V 1 and V 2 may independently be present or absent; wherein each of V 1 and V 2 , if present, independently represents a covalent bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 , C=O, SiR 7 R 8 , GeR 7 R 8 , NR 7 、PR 7 、PR 7 R 8 、R 7 P=O, AsR 7 、R 7 As=O, S=O, SO 2 、Se=O, SeO 2 、BR 7 、BR 7 R 8 、 AlR 7 、AlR 7 R 8 、R 7 Bi = O or BiR 7 ; where when V 1 does not exist, then L 4 does not combine with L 5 ; and When V 2 does not exist, then L 6 does not combine with L 5 ; V 3 is present or absent, where V 3 if present, represents a covalent bond, C, N, Si, O, S, Ge, P, As, Se, B, Al or Bi, or, if valency permits, each independently represents CR 7 、SiR 7 、 GeR 7 、NR 7 、P=O, As=O, B, BR 7 、AlR 7 、Bi=O, CR 7 R 8 、C=O, SiR 7 R 8 、GeR 7 R 8 、 NR 7 、PR 7 、PR 7 R 8 、R 7 P=O, AsR 7 、R 7 As=O, S=O, SO 2 、Se=O, SeO 2 、BR 7 、BR 7 R 8 、 AlR 7 、AlR 7 R 8 、R 7 Bi = O or BiR 7 ; where when V 3 does not exist, then Y 2a directly combines with Y 2b ; and Each n is independently an integer, subject to valence requirements.

5. The compound according to claim 2, wherein the compound is represented by general formula XIV, general formula XV, general formula XVI or general formula XVII: Wherein: Y 1a 、Y 1b 、Y 1c 、Y 1d 、Y 2a 、Y 2b 、Y 3a 、Y 3b 、Y 4e 、Y 4f 、Y 4g 、Y 4h 、Y 5a 、Y 5b 、Y 5c and Y 5d each independently represents C or N; Z 1 , Z 2 , Z 3 and Z 4 Each independently represents C or N; C and D each independently represent C, N, O or S; X represents a single bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 、C=O、SiR 7 R 8 、GeR 7 R 8 、 NR 7 、PR 7 、PR 7 R 8 、R 7 P=O, AsR 7 、R 7 As=O, S=O, SO 2 、Se=O, SeO 2 、BR 7 、BR 7 R 8 、AlR 7 、AlR 7 R 8 、R 7 Bi=O or BiR 7 ,or X is absent, where when X is absent, L 4 has no bond with the ring including Z 2 ; X 1 and X 2 each independently represents a single bond, O, S, Se, P═O, As═O, Bi═O, CR 7 R 8 , C═O, SiR 7 R 8 , GeR 7 R 8 , NR 7 , PR 7 , PR 7 R 8 , R 7 , P═O, AsR 7 , R 7 , As═O, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 , Bi═O or BiR 7 ; R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 and R 10 each independently is absent or, where valency permits, is present as a single substituent or as multiple substituents, and R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 and R 10 each independently represents hydrogen, deuterium, halogen, hydroxy, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxy, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; or R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 and R 10 any two of which represent a covalent bond; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 ,X,X 1 and X 2 Any two of may together form a fused ring; L 4 、L 5 and L 6 each independently represents a 5- to 10-membered aryl, heteroaryl, fused aryl or fused heteroaryl; L 5 Present or absent; V 1 and V 2 may exist independently or not; wherein each of V 1 and V 2 , if present, independently represents a covalent bond, O, S, Se, P═O, As═O, Bi═O, CR 7 R 8 , C═O, SiR 7 R 8 , GeR 7 R 8 , NR 7 、PR 7 、PR 7 R 8 、R 7 P=O, AsR 7 、R 7 As=O, S=O, SO 2 、Se=O, SeO 2 、BR 7 、BR 7 R 8 、 AlR 7 、AlR 7 R 8 、R 7 Bi = O or BiR 7 ; where when V 1 does not exist, then L 4 does not combine with L 5 ; and When V 2 does not exist, then L 6 does not combine with L 5 ; V 3 is present or absent, where V 3 if present, represents a covalent bond, C, N, Si, O, S, Ge, P, As, Se, B, Al or Bi, or, if valency permits, each independently represents CR 7 、SiR 7 、 GeR 7 、NR 7 、P=O, As=O, B, BR 7 、AlR 7 、Bi=O, CR 7 R 8 、C=O, SiR 7 R 8 、GeR 7 R 8 、 NR 7 、PR 7 、PR 7 R 8 、R 7 P=O, AsR 7 、R 7 As=O, S=O, SO 2 、Se=O, SeO 2 、BR 7 、BR 7 R 8 、 AlR 7 、AlR 7 R 8 、R 7 Bi = O or BiR 7 ; where when V 3 does not exist, then Y 2a directly combines with Y 2b ; and Each n is independently an integer, subject to valence requirements.

6. The compound according to claim 2, wherein the compound is represented by general formula XVIII, general formula XIX, general formula XX or general formula XXI: Wherein: Y 2a 、Y 2b 、Y 3a 、Y 3b 、Y 4e 、Y 4f 、Y 4g 、Y 4h 、Y 5a 、Y 5b 、Y 5c and Y 5d each independently represents C or N; Z 1 , Z 2 , Z 3 and Z 4 Each independently represents C or N; A, B, C and D each independently represent C, N, O or S; X represents a single bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 、C=O, SiR 7 R 8 、GeR 7 R 8 、 NR 7 、PR 7 、PR 7 R 8 、R 7 P=O, AsR 7 、R 7 As=O, S=O, SO 2 、Se=O, SeO 2 、BR 7 、BR 7 R 8 、AlR 7 、AlR 7 R 8 、R 7 Bi=O or BiR 7 , or X is absent, where when X is absent, L 4 has no bond with the ring including Z 2 ; X 1 and X 2 each independently represents a single bond, O, S, Se, P═O, As═O, Bi═O, CR 7 R 8 , C═O, SiR 7 R 8 , GeR 7 R 8 , NR 7 , PR 7 , PR 7 R 8 , R 7 , P═O, AsR 7 , R 7 , As═O, S═O, SO 2 , Se═O, SeO 2 , BR 7 , BR 7 R 8 , AlR 7 , AlR 7 R 8 , R 7 , Bi═O or BiR 7 ; Y 1 and Y 2 each independently represents hydrogen, deuterium, halogen, hydroxy, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxy, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; wherein Y 1 and Y 2 may optionally together form a fused aromatic or heteroaromatic ring; R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 and R 9 each of which independently is absent or, where valence allows, is present in the form of a single substituent or multiple substituents, and R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 and R 9 each independently represents hydrogen, deuterium, halogen, hydroxy, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxy, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; or 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 and R 9 any two of which represent a covalent bond; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 ,X,X 1 and X 2 Any two of may together form a fused ring; L 4 、L 5 and L 6 each independently represents a 5- to 10-membered aryl, heteroaryl, fused aryl or fused heteroaryl; L 5 Present or absent; V 1 and V 2 are independently present or absent; wherein each of V 1 and V 2 , if present, independently represents a covalent bond, O, S, Se, P=O, As=O, Bi=O, CR 7 R 8 , C=O, SiR 7 R 8 , GeR 7 R 8 , NR 7 、PR 7 、PR 7 R 8 、R 7 P=O, AsR 7 、R 7 As=O, S=O, SO 2 、Se=O, SeO 2 、BR 7 、BR 7 R 8 、 AlR 7 、AlR 7 R 8 、R 7 Bi = O or BiR 7 ; where when V 1 does not exist, then L 4 does not combine with L 5 ; and When V 2 is absent, then L 6 does not combine with L 5 ; V 3 is present or absent, where V 3 if present, represents a covalent bond, C, N, Si, O, S, Ge, P, As, Se, B, Al or Bi, or, if valency permits, independently represents CR 7 、SiR 7 、 GeR 7 、NR 7 、P=O、As=O、B、BR 7 、AlR 7 、Bi=O、CR 7 R 8 、C=O、SiR 7 R 8 、GeR 7 R 8 、 NR 7 、PR 7 、PR 7 R 8 、R 7 P=O, AsR 7 、R 7 As=O, S=O, SO 2 、Se=O, SeO 2 、BR 7 、BR 7 R 8 、 AlR 7 、AlR 7 R 8 、R 7 Bi = O or BiR 7 ; where when V 3 does not exist, then Y 2a directly combines with Y 2b ; and Each n is independently an integer, subject to valence requirements.

7. The compound according to claim 1, wherein Is represented by one of the following structures: Wherein: M represents Pt(II) or Pd(II); Y 1a 、Y 1b 、Y 1c 、Y 1d 、Y 3a 、Y 3b 、Y 4e 、Y 4f 、Y 4g 、Y 4h 、Y 5a 、Y 5b 、Y 5c and Y 5d each independently represents C or N; X 1 and X 2 each independently represents a single bond, O, S, Se, P═O, As═O, Bi═O, CR 7 R 8 , C═O, SiR 7 R 8 、GeR 7 R 8 、NR 7 、PR 7 、PR 7 R 8 、R 7 P=O、AsR 7 、R 7 As=O、S=O、SO 2 、Se=O、 SeO 2 、BR 7 、BR 7 R 8 、AlR 7 、AlR 7 R 8 、R 7 Bi = O or BiR 7 ; R 1 、R 6 、R 7 、R 8 、R 9 and R 10 each independently is absent or, where valency permits, is present as a single substituent or as multiple substituents, and R 1 、R 6 、R 9 and R 10 each independently represents hydrogen, deuterium, halogen, hydroxy, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxy, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; or 1 、R 6 、R 9 and R 10 any two of which represent a covalent bond; R 1 、R 6 、R 9 and R 10 Any two of them can form a fused ring together; Each n is independently an integer, subject to valence requirements.

8. The compound according to claim 1, wherein Is represented by one of the following structures: Wherein: Y 1a 、Y 1b 、Y 1c 、Y 1d 、Y 2a 、Y 2b 、Y 2c 、Y 2d 、Y 3a 、Y 3b and Y 3c each independently represents C or N; R 1 、R 2 、R 3 、R 4 、R 5 each of which independently does not exist or, where valency permits, exists in the form of a single substituent or multiple substituents, and R 1 、R 3 、R 4 、R 5 、R 6 and R 7 each independently represents deuterium, halogen, hydroxyl, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof.

9. The compound according to claim 1, wherein Is represented by one of the following structures: Wherein: Y 1a 、Y 1b 、Y 1c 、Y 1d 、Y 1e 、Y 1f and Y 1g each independently represents C or N; R 1 and R 2 each independently is absent or, where valence permits, is present as a single substituent or multiple substituents, and R 1 and R 2 each independently represents deuterium, halogen, hydroxy, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, thiol, sulfo, carboxy, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; and R 1 and R 2 any two of which may join together to form a ring; Y 1 , Y 2 , Y 3 and Y 4 each independently does not exist or exists, and Y 1 , Y 2 , Y 3 and Y 4 each independently represents hydrogen, deuterium, halogen, hydroxyl, mercapto, nitro, cyano, nitrile, isonitrile, sulfinyl, sulfhydryl, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclic group, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymer; or any conjugate or combination thereof; and Y 1 , Y 2 , Y 3 and Y 4 Any two of the may be joined together to form a ring.

10. The compound according to claim 1, wherein the compound is selected from the following structures:

11. An organic light-emitting diode comprising the compound according to claim 1.

12. An organic light-emitting diode comprising the compound according to claim 3.

13. An organic light-emitting diode comprising the compound according to claim 4.

14. An organic light-emitting diode comprising the compound according to claim 5.

15. An organic light-emitting diode comprising the compound according to claim 6.

16. A light-emitting device comprising the light-emitting diode according to claim 11.

17. A light-emitting device comprising the light-emitting diode according to claim 12.

18. A light-emitting device comprising the light-emitting diode according to claim 13.

19. A light-emitting device comprising the light-emitting diode according to claim 14.

20. A light-emitting device comprising the light-emitting diode according to claim 15.

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