Dinuclear platinum complexes for OLED applications
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- THE UNIVERSITY OF HONG KONG
- Filing Date
- 2023-07-05
- Publication Date
- 2026-07-01
AI Technical Summary
Existing blue emitters for OLEDs face challenges with low quantum efficiency, short operational lifetime, and long radiative lifetime, limiting device performance and stability.
Development of dinuclear platinum(II) emitter complexes with tridentate N-heterocyclic carbene cyclometalating ligands, which are phosphorescent and electroluminescent, capable of emitting light in the blue wavelength range and are photostable and thermostable, suitable for incorporation into OLEDs.
The complexes enhance operational stability and efficiency of OLEDs, extending their lifetime and improving performance by adjusting radiative lifetime, making them suitable for various display and illumination applications.
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Abstract
Description
[Technical field]
[0001] (CROSS REFERENCE TO RELATED APPLICATIONS) This application claims the benefit of and priority to U.S. Patent Application No. 63 / 393,021, filed July 28, 2022, the entire contents of which are incorporated by reference in this disclosure.
[0002] FIELD OF THEINVENTION The invention of the present disclosure relates generally to the field of emitter platinum (II) dinuclear complexes, in particular blue emitter platinum (II) dinuclear complexes (containing cyclometalating tridentate ligands), and their use in organic electronics, e.g., organic light-emitting devices (OLEDs). [Background technology]
[0003] BACKGROUND OF THEINVENTION Transition metal complexes have attracted considerable interest in commercial and academic settings as molecular probes, catalysts and luminescent materials. As luminescent materials, transition metal complexes are increasingly being developed as potential alternatives to purely organic materials because they have the potential for improved luminescence efficiency and device stability compared to purely organic materials. Summary of the Invention [Problem to be solved by the invention]
[0004] The search for a stable and highly efficient blue emitter in operation continues but has proved insurmountable. Thus, the development of new emitters remains a valuable target in the OLED industry. Active efforts in this field have been directed towards the research and development of new phosphorescent metal complexes. Recently, thermally activated delayed fluorescent (TADF) compounds have been developed. Such compounds are due to their intrinsic advantages in achieving high efficiency in the operation of devices. To date, such efforts have resulted in limited success for these classes of emitter complexes. In such a class, issues remain, for example, regarding low quantum efficiency, short operational lifetime and long radiative lifetime of the emitters. Therefore, the performance and operational stability of the device / lifetime of metal-based OLEDs must be improved for practical applications.
[0005] Thus, there remains a need to develop highly efficient emitter complexes with improved operational stability for OLED applications, and to extend the operational lifetime of devices containing such emitters to a more practical level by adjusting the radiative lifetime of the emitters.
[0006] It is therefore an object of the present invention to provide new luminescent transition metal binuclear complexes comprising platinum(II) and a cyclometalating tridentate ligand.
[0007] Another object of the present invention is to provide new luminescent fluorine-free dinuclear transition metal complexes containing platinum(II) and a cyclometalating tridentate ligand. [Means for solving the problem]
[0008] Summary of the Invention The dinuclear platinum emitter complex contains a platinum(II) atom complexed with a tridentate N-heterocyclic carbene cyclometalating CCN ligand (or tridentate N-heterocyclic carbene cyclometalating CCN ligand). Such ligands include phenyl rings, imidazolyl N-heterocyclic carbene rings, and pyrazole rings. For example, the dinuclear platinum emitter complex may have the structure of Formula IIa or IIb as follows: [ka] Formula IIa or [ka] Formula IIb
[0009] During the ceremony The compound has an overall neutral, negative or positive charge.
[0010] A dashed straight line indicates the presence or absence of a bond.
[0011] Preferably, X5 and X 5’ is carbon.
[0012] Preferably, X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X 4’ is independently carbon, nitrogen, oxygen, or sulfur, if present, and is independently bonded to one hydrogen atom or to no hydrogen atoms, depending on the valency.
[0013] Preferably, R5, R6, R 5’ and R 6’ are independently hydrogen, substituted alkyl, unsubstituted alkyl, substituted aryl, or unsubstituted aryl, or R5, R6, R 5’ and R 6’ together with the atom to which they are attached, represent substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 heterocyclyl, which form fused combinations (or combinations thereof which are fused).
[0014] Preferably, A1, A2, A3, A4, A 1’ , A 2’ , A 3’ and A 4’ is independently absent, hydrogen, deuterium, carbon, nitrogen, unsubstituted aryl, or substituted and, if present, is independently bonded to 1, 2, 3, 4, 5, or no hydrogen atoms, depending on the valency.
[0015] Preferably, R 1a , R 2a , R 3a , R 4a , R 1a’ , R 2a’ , R 3a’ and R 4a’ is independently absent, hydrogen, deuterium, substituted alkyl, unsubstituted alkyl, substituted aryl, unsubstituted aryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 heterocyclyl, a fused combination thereof (or a fused combination thereof) (e.g., dibenzofuran-4-yl, dibenzofuran-3-yl, dibenzothiopen-4-yl, dibenzothiopen-3-yl, etc.), or R 1a and R 2a , R 2a and R 3a , R 3a and R 4a , R 1a’ and R 2a’ , R 2a’ and R 3a’ , R 3a’ and R 4a’ or any combination thereof, taken together with the atom to which they are attached, is substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyaryl, unsubstituted polyaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20heterocyclyl, which form fused combinations (or combinations thereof which are fused).
[0016] Preferably, R1, R2, R3, R4, R 1’ , R 2’ , R 3’ and R 4’ are independently absent, hydrogen, deuterium, substituted alkyl (e.g., trifluoromethyl), unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, substituted aryl (e.g., mesityl (2,4,6-trimethylphenyl), 3,5-di-tert-butylphenyl, 2,6-dimethylphenyl), unsubstituted aryl, halogen (e.g., fluorine), or R1 and R2, R2 and R3, R3 and R4, R 1’ and R 2’ , R 2’ and R 3’ , R 3’ and R 4’ or any combination thereof, together with the atom to which they are attached, represents substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 heterocyclyl, or a fused combination thereof (or a fused combination thereof).
[0017] and / or preferably, L1 and L 1’ are independently substituted C1-C 10 Alkyl or unsubstituted C1-C 10 Preferably, the substituted C-C alkyl 10An alkyl group can have one or more alkyl substituents (e.g., methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl), one or more ether linkages, one or more amine groups (e.g., substituted or unsubstituted amines), one or more substituted aryl groups, one or more substituted heteroaryl groups, one or more substituted C-C 20 Cycloalkyl groups, one or more substituted C1-C 20 L and L 1’ It should be understood that is at least divalent.
[0018] In some forms, the compound may have any one of the following structures: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0019] The dinuclear platinum emitter complex described in the present disclosure is phosphorescent (or phosphorescent) and / or electroluminescent (or EL-emitting or electroluminescent). The dinuclear platinum emitter complex may be luminescent (or can emit light) at room temperature, low temperature, or both. The dinuclear platinum emitter complex may be in the form of a solid, liquid, glass, film, or solution. The dinuclear platinum emitter complex may be luminescent (or can emit light) in response to (i) the passage of electric current, or (ii) an electric field. In some forms, the dinuclear platinum emitter complex may be luminescent (or can emit light) independent of concentration. The phosphorescent (or phosphorescent or phosphorescent) and / or electroluminescent (or EL-emitting or electroluminescent) properties of the emitter platinum dinuclear complex are typically within the wavelength range of about 380 nm to about 550 nm, inclusive. In some embodiments, the emitter platinum dinuclear complex preferably emits blue to deep blue light within the wavelength range of about 400 nm to about 550 nm, inclusive, or any range (or subrange) below. The emission properties of the emitter platinum dinuclear complex can be adjusted (or modified) by the selection of substituents. The emitter platinum dinuclear complex can emit exclusively or predominantly in the blue wavelength range of the visible spectrum. It can also include one or two emission maxima (or maxima) within that range.
[0020] Preferably, the emitter platinum(II) dinuclear complexes described in the present disclosure are photostable, thermally stable and / or luminescent at room temperature, low temperature or a combination thereof, and thus such complexes can be included (or incorporated) in OLEDs. Such OLEDs are useful in commercial applications such as visual display units, mobile visual display units, illumination units, keyboards, clothes, ornaments, garment accessories, wearable devices, medical monitoring devices, wallpaper, tablet computers, laptops, advertisement panels, panel display units, household appliances or office appliances. It can be used in a variety of applications. [Brief description of the drawings]
[0021] [Figure 1A]FIG. 1A is a line graph showing electroluminescence data for an OLED fabricated with Pt-1. The doping concentrations are 4 wt% to 16 wt% (e.g., 4 wt%, 8 wt%, 16 wt%). The device structure is as follows: ITO / HAT-CN(5 nm) / TAPC(40 nm) / TcTa(7 nm) / CzSi(3 nm) / Pt-1:CzSi(10 nm) / TSPO1(30 nm) / LiF(1 nm) / Al(100 nm). [Figure 1B] FIG. 1B is a line graph showing electroluminescence data for an OLED fabricated with Pt-1. The doping concentrations are 4 wt% to 16 wt% (e.g., 4 wt%, 8 wt%, 16 wt%). The device structure is as follows: ITO / HAT-CN(5 nm) / TAPC(40 nm) / TcTa(7 nm) / CzSi(3 nm) / Pt-1:CzSi(10 nm) / TSPO1(30 nm) / LiF(1 nm) / Al(100 nm). [Figure 1C] FIG. 1C is a line graph showing electroluminescence data for an OLED fabricated with Pt-1. The doping concentrations are 4 wt% to 16 wt% (e.g., 4 wt%, 8 wt%, 16 wt%). The device structure is as follows: ITO / HAT-CN(5 nm) / TAPC(40 nm) / TcTa(7 nm) / CzSi(3 nm) / Pt-1:CzSi(10 nm) / TSPO1(30 nm) / LiF(1 nm) / Al(100 nm). [Figure 1D]FIG. 1D is a line graph showing electroluminescence data for an OLED fabricated with Pt-1. The doping concentrations are 4 wt% to 16 wt% (e.g., 4 wt%, 8 wt%, 16 wt%). The device structure is as follows: ITO / HAT-CN(5 nm) / TAPC(40 nm) / TcTa(7 nm) / CzSi(3 nm) / Pt-1:CzSi(10 nm) / TSPO1(30 nm) / LiF(1 nm) / Al(100 nm). [Diagram 2] 2 shows a non-limiting example of an organic light-emitting diode (OLED) device 100 having a multilayer architecture. The device includes the following: (i) a cathode 110 (including a first layer 120 and a second layer 130); (ii) an electron transport layer 140 (or electron transport layer or electron transport layer or electron transporting layer 140); (iii) an optional carrier confinement layer 150 (or carrier confinement layer 150); (vi) an emissive layer 160; (v) a hole transport layer 170 (or hole transport layer or hole transport layer 170); and (vi) an anode 180. [Diagram 3] Figure 3 is a line graph showing the emission spectra of Pt-1 and Pt-2 (in PMMA film). DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0022] Detailed Description of the Invention I. Definitions (or Provisions) "Substituted," as used herein, refers to all possible substitutions in a compound or functional group described in this disclosure. In a broad sense, such possible substitutions include acyclic and cyclic, branched and unbranched, carbocyclic or heterocyclic, aromatic and nonaromatic substitutions in organic compounds. Exemplary substitutions include, but are not limited to, halogens, hydroxyl groups, or any other organic grouping containing any number of carbon atoms, preferably 1-14 carbon atoms, optionally containing one or more heteroatoms (e.g., oxygen, sulfur, or nitrogen), in a linear, branched, or cyclic structural format. Representative substituents include substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted phenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted aralkyl, halogen, hydroxyl, alkoxy, phenoxy, aroxy, silyl, thiol, alkylthio, substituted alkylthio, phenylthio, arylthio, cyano, isocyano, nitro, substituted or unsubstituted carbonyl, carboxyl, amino, amido, oxo, sulfinyl, sulfonyl, sulfonic acid, phosphonium, phosphanyl, phosphoryl, phosphonyl, amino acid. Such substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted phenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted aralkyl, halogen, hydroxyl, alkoxy, phenoxy, aroxy, silyl, thiol, alkylthio, substituted alkylthio, phenylthio, arylthio, cyano, isocyano, nitro, substituted or unsubstituted carbonyl, carboxyl, amino, amido, oxo, sulfinyl, sulfonyl, sulfonic acid, phosphonium, phosphanyl, phosphoryl, phosphonyl and amino acid may be further substituted.
[0023] Heteroatoms (e.g., nitrogen) may have hydrogen substituents and / or any of the possible substituents of organic compounds described herein, provided that they satisfy the valences of the heteroatoms. It is understood that "substituted" or "substituted" includes an implicit meaning, provided that such substitutions are subject to the possible valences of the atom and the substitution. It is also understood that such substitutions result in stable compounds (i.e., compounds that do not spontaneously undergo transformation (e.g., by rearrangement, cyclization, elimination, etc.).
[0024] "Alkyl," as used in this disclosure, refers to the group (or radical) of a saturated aliphatic group, including straight chain alkyl groups, branched chain alkyl, and cycloalkyl (alicyclic). In some embodiments, a straight chain or branched chain alkyl has 30 or fewer, 20 or fewer, 15 or fewer, or 10 or fewer carbon atoms in its backbone (e.g., C1-C4 for a straight chain). 30 , C3-C for branched chains 30 ). Alkyl includes the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, hexyl, heptyl, octyl, decyl, tetradecyl, hexadecyl, eicosyl, tetracosyl, and the like. Similarly, cycloalkyl is a non-aromatic carbon-based ring made up of at least three carbon atoms (e.g., a non-aromatic monocyclic ring or non-aromatic polycyclic rings having from 3-30 carbon atoms, 3-20 carbon atoms, or 3-10 carbon atoms in the ring structure, 5, 6, or 7 carbons in the ring structure). Cycloalkyls including polycyclic ring systems can have more than one non-aromatic ring. In this ring, two or more carbons are common to two adjacent rings (i.e., "fused cycloalkyl rings"). Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and the like.
[0025] "Substituted alkyl" refers to an alkyl moiety having one or more substituents replacing a hydrogen on one or more carbons of its hydrocarbon backbone. Such substituents can be any of the substituents described above, such as halogen (e.g., fluorine, chlorine, bromine, or iodine), hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), thiocarbonyl (e.g., thioester, thioacetate, or thioformate), aryl, alkoxyl, aralkyl, phosphonium, phosphanyl, phosphonyl, phosphoryl, phosphate, phosphonate, phosphinate, amino, amido, amidine, imine, cyano, nitro, azido, oxo, sulfhydryl, thiol, alkylthio, silyl, sulfinyl, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, aromatic ... or heteroaromatic moieties, -NRR', where R and R' are independently hydrogen, alkyl or aryl, and the nitrogen atom may be optionally quaternized; -SR, where R is phosphonyl, sulfinyl, silyl, hydrogen, alkyl or aryl; -CN; -NO; -COOH; carboxylate; -COR, -COOR or -CON(R)2, where R is hydrogen, alkyl or aryl; imino, silyl, ether, haloalkyl (e.g., -CF3, -CH2-CF3, -CCl3); -CN; -NCOCOCH2CH2; -NCOCOCHCH; and -NCS; and combinations thereof.
[0026] It will be understood by those skilled in the art that the moieties substituted on the hydrocarbon chain may themselves be substituted, if appropriate. For example, substituted alkyl substituents may include halogen, hydroxy, nitro, thiol, amino, aralkyl, azido, imino, amide, phosphonium, phosphanyl, phosphoryl (including phosphonates and phosphinates), oxo, sulfonyl (including sulfates, sulfonamides, sulfamoyls and sulfonates), and silyl groups, as well as ethers, alkylthio, carbonyl (including ketones, aldehydes, carboxylates and esters), haloalkyl, -CN, and the like. Cycloalkyls may be substituted in the same manner.
[0027] Unless the number of carbons is otherwise specifically recited, "lower alkyl," as used in this disclosure, means an alkyl group, as defined (or specified) above, but having from 1 to 10 carbons, more preferably 1 to 6 carbon atoms, in its backbone structure. Similarly, "lower alkenyl" and "lower alkynyl" have similar chain lengths.
[0028] "Heteroalkyl" as used herein means a linear or branched or cyclic carbon-containing alkyl group, or a combination thereof, containing at least one heteroatom in its carbon skeleton. Suitable heteroatoms include, but are not limited to, O, N, Si, P, and S, where the nitrogen, phosphorus, and sulfur atoms may be optionally oxidized. The nitrogen heteroatom may be optionally quaternized. For example, the term "heterocycloalkyl group" refers to a cycloalkyl group (as defined above) in which at least one of the carbon atoms of the ring is replaced with a heteroatom (such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus).
[0029] The term "alkenyl" as used herein refers to a hydrocarbon group having 2-24 carbon atoms whose structural formula contains at least one carbon-carbon double bond. Alkenyl groups include straight-chain alkenyl groups, branched-chain alkenyls, and cycloalkenyls. Cycloalkenyls are non-aromatic carbon-based rings that are composed of at least three carbon atoms and at least one carbon-carbon double bond. For example, a non-aromatic monocyclic or non-aromatic polycyclic ring may contain 3-30 carbon atoms and at least one carbon-carbon double bond in its ring structure, or 3-20 carbon atoms and at least one carbon-carbon double bond, or 3-10 carbon atoms and at least one carbon-carbon double bond, or 5, 6, or 7 carbons and at least one carbon-carbon double bond in its ring structure. Cycloalkenyls, including polycyclic ring systems, may have more than one non-aromatic ring. In this ring, two or more carbons are common to two adjacent rings (i.e., a "fused cycloalkenyl ring") and contain at least one carbon-carbon double bond. Asymmetric structures (e.g., (AB)C=C(C'D)) are intended to include both the E and Z isomers (or isomers). This may be assumed in the structural formula. In the structural formula, an asymmetric alkene is present. Alternatively, this may be indicated explicitly by the bond symbol (C). The term "alkenyl," as used throughout the specification, examples, and claims, is intended to include both "unsubstituted alkenyl" and "substituted alkenyl." The latter ("substituted alkenyl") refers to an alkenyl moiety having one or more substituents replacing a hydrogen on one or more carbons of its hydrocarbon skeleton (or hydrocarbon backbone). The term "alkenyl" also includes "heteroalkenyl."
[0030] The term "substituted alkenyl" refers to an alkenyl moiety having one or more substituents replacing one or more hydrogen atoms on one or more carbons of its hydrocarbon backbone. Such substituents may be any of the substituents described above. For example, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxyl, phosphonium, phosphanyl, phosphoryl, phosphate, phosphonate, phosphinate, amino (e.g., quaternized amino), amido, amidine, imine, cyano, nitro, azido, oxo, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, polyaryl, polyheteroaryl, and combinations thereof.
[0031] "Heteroalkenyl" as used herein means a straight or branched chain or cyclic carbon-containing alkenyl group, or a combination thereof, containing at least one heteroatom (or heteroatom). Suitable heteroatoms (or heteroatoms) include, but are not limited to, O, N, Si, P, and S, where the nitrogen, phosphorus, and sulfur atoms may be optionally oxidized. The nitrogen heteroatom (or heteroatom) may be optionally quaternized. For example, the term "heterocycloalkenyl group" refers to a cycloalkenyl group in which at least one carbon atom of the ring is replaced with a heteroatom (or heteroatom), such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus.
[0032] The term "alkynyl group" as used herein refers to a hydrocarbon group of 2 to 24 carbon atoms, the structural formula of which includes at least one carbon-carbon triple bond. Alkynyl groups include straight chain alkynyl groups, branched chain alkynyl and cycloalkynyl. Cycloalkynyl is a non-aromatic carbon-based ring that is composed of at least three carbon atoms and at least one carbon-carbon triple bond in its ring structure. For example, it is a non-aromatic monocyclic ring or a non-aromatic polycyclic ring that is composed of 3 to 30 carbon atoms and at least one carbon-carbon triple bond in its ring structure, or 3 to 20 carbon atoms and at least one carbon-carbon triple bond, or 3 to 10 carbon atoms and at least one carbon-carbon triple bond, and has 5, 6 or 7 carbons and at least one carbon-carbon triple bond in its ring structure. Cycloalkynyls, including polycyclic ring systems, can have two or more non-aromatic rings where two or more carbons are common to two adjacent rings (i.e., "fused cycloalkynyl rings") and contain at least one carbon-carbon triple bond. For example, the asymmetric structure [ka] is intended to include both the E and Z isomers, in which the structural formula may be assumed. In the structural formula, an asymmetric alkyne exists. Alternatively, this may be explicitly indicated by the bond symbol (C). The term "alkynyl", as used throughout the specification, examples, and claims, is intended to include both "unsubstituted alkynyl" and "substituted alkynyl". The latter (or "substituted alkynyl") refers to an alkynyl moiety having one or more substituents replacing a hydrogen on one or more carbons of its hydrocarbon backbone. The term "alkynyl" also includes "heteroalkynyl".
[0033] The term "substituted alkynyl" refers to an alkynyl moiety having one or more substituents replacing one or more hydrogen atoms on one or more carbons of its hydrocarbon backbone. Such substituents may be any of the substituents described above. For example, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxyl, phosphonium, phosphanyl, phosphoryl, phosphate, phosphonate, phosphinate, amino (e.g., quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, polyaryl, polyheteroaryl, and combinations thereof.
[0034] "Heteroalkynyl" as used herein means a linear or branched or cyclic carbon-containing alkynyl group, or a combination thereof, containing at least one heteroatom (or heteroatom). Suitable heteroatoms (or heteroatoms) include, but are not limited to, O, N, Si, P, and S, where the nitrogen, phosphorus, and sulfur atoms may be optionally oxidized. The nitrogen heteroatom (or heteroatom) may be optionally quaternized. For example, the term "heterocycloalkynyl group" refers to a cycloalkynyl group in which at least one carbon atom of the ring is replaced with a heteroatom (or heteroatom), such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus.
[0035] "Aryl," as used herein, refers to any C5-C 26Examples of aromatic groups are benzene, naphthalene, anthracene, phenanthrene, chrysene, pyrene, corannulene, coronene, and the like.
[0036] The term "substituted aryl" refers to an aryl group in which one or more hydrogen atoms on one or more aromatic rings are replaced with one or more substituents. Substituents include, but are not limited to, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, alkoxy, carbonyl (e.g., ketone, aldehyde, carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxyl, phosphoryl, phosphate, phosphonate, phosphinate, amino (or quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, imino, alkylthio, sulfate, sulfonate, sulfamoyl, sulfoxide, sulfonamide, sulfonyl, heterocyclyl, alkylaryl, haloalkyl (e.g., -CF3, -CH2-CF3, -CCl3), -CN, aryl, heteroaryl, and combinations thereof.
[0037] The terms "heterocycle" and "heterocyclyl" are used interchangeably and refer to a cyclic group bonded by ring carbon or nitrogen atoms of a non-aromatic monocyclic or polycyclic ring containing 3-30 ring atoms, 3-20 ring atoms, 3-10 ring atoms, or 5-6 ring atoms, where each ring contains carbon atoms and 1-4 heteroatoms (or heteroatoms), each of which is selected from the group consisting of oxygen (not peroxides), sulfur, and N(Y), where Y is absent or selected from H, O, C1-C2, 10, phenyl or benzyl. Optionally, it may contain 1 to 3 double bonds. Optionally, it may be substituted with one or more substituents. Heterocyclyl is distinct from heteroaryl by definition. Heterocyclyl may be heterocycloalkyl, heterocycloalkenyl, heterocycloalkynyl, etc. Examples include piperazinyl, piperidinyl, piperidonyl, 4-piperidonyl, dihydrofuro[2,3-b]tetrahydrofuran, morpholinyl, piperazinyl, piperidinyl, piperidonyl, 4-piperidonyl, piperonyl, pyranyl, 2H-pyrrolyl, 4H-quinolizinyl, quinuclidinyl, tetrahydrofuranyl, 6H-1,2,5-thiadiazinyl. Heterocyclic groups (or heterocyclic or heterocyclic groups) may be substituted with one or more substituents as defined above for alkyl and aryl.
[0038] The term "heteroaryl" refers to any heteroaryl having a C5-C 26means an aromatic or fused aromatic ring system of any one of the members, in which one or more carbon atoms of one or more of the aromatic ring structures are replaced with a heteroatom. Suitable heteroatoms include, but are not limited to, oxygen, sulfur, and nitrogen. Examples of heteroaryl groups include pyrrole, furan, thiophene, imidazole, oxazole, thiazole, triazole, tetrazole, pyrazole, pyridine, pyrazine, pyridazine, pyrimidine, and the like.Examples of heteroaryl rings include, but are not limited to, benzimidazolyl, benzofuranyl, benzothiofuranyl, benzothiophenyl, benzoxazolyl, benzoxazolinyl, benzthiazolyl, benztriazolyl, benztetrazolyl, benzisoxazolyl, benzisothiazolyl, benzimidazolinyl, carbazolyl, 4aH-carbazolyl, carbolinyl, chromanyl, chromenyl, cinnolinyl, decahydroquinolinyl, and the like. , 2H,6H-1,5,2-dithiazinyl, furanyl, furazanyl, imidazolidinyl, imidazolinyl, imidazolyl, 1H-indazolyl, indolenyl, indolinyl, indolizinyl, indolyl, 3H-indolyl, isatinoyl, isobenzofuranyl, isochromanyl, isoindazolyl, isoindolinyl, isoindolyl, isoquinolinyl, isothiazolyl, isoxazolyl, methylenedioxyphenyl, naphthyridinyl, octahydroisoquinolinyl, 1,2, 3-Oxadiazolyl, 1,2,4-Oxadiazolyl, 1,2,5-Oxadiazolyl, 1,3,4-Oxadiazolyl, Oxazolidinyl, Oxazolyl, Oxindolyl, Pyrimidinyl, Phenanthridinyl, Phenanthrolinyl, Phenazinyl, Phenothiazinyl, Phenoxathinyl, Phenoxazinyl, Phthalazinyl, Pteridinyl, Purinyl, Pyrazinyl, Pyrazolidinyl, Pyrazolinyl, Pyrazolyl, Pyridazinyl, Pyridoxazole, Pyridoimidazole, Pyri Dothiazole, pyridinyl, pyridyl, pyrimidinyl, pyrrolidinyl, pyrrolinyl, pyrrolyl, quinazolinyl, quinolinyl, quinoxalinyl, tetrahydroisoquinolinyl, tetrahydroquinolinyl, tetrazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, thianthrenyl, thiazolyl, thienyl, thienothiazolyl, thienoxazolyl, thienoimidazolyl, thiophenyl, and xanthenyl. One or more rings may be substituted as defined (or specified) below for "substituted heteroaryl."
[0039] The term "substituted heteroaryl" refers to a heteroaryl group in which one or more hydrogen atoms in one or more of the heteroaromatic rings (or heteroaromatic rings) are replaced with one or more substituents. Substituents include, but are not limited to, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, alkoxy, carbonyl (e.g., ketone, aldehyde, carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxyl, phosphoryl, phosphate, phosphonate, phosphinate, amino (or quaternized amino), amido, amidine, imine, cyano, nitro, azide, sulfhydryl, imino, alkylthio, sulfate, sulfonate, sulfamoyl, sulfoxide, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl (e.g., -CF3, -CH2-CF3, -CCl3), -CN, aryl, heteroaryl, and combinations thereof.
[0040] The term "polyaryl" refers to a chemical moiety that contains two or more fused aryl groups. If two or more fused heteroaryl groups are included, the chemical moiety can be called a "polyheteroaryl."
[0041] The term "substituted polyaryl" refers to a polyaryl in which one or more aryls are substituted with one or more substituents. The substituents include, but are not limited to, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxyl, phosphoryl, phosphate, phosphonate, phosphinate, amino (or quaternized amino), amide, amidine, imine, cyano, nitro, azide, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfoxide, sulfonamide, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof. When polyheteroaryl is included, such chemical moieties can be referred to as "substituted polyheteroaryls."
[0042] The term "cyclic ring" or "cyclic group" means a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted polycyclic ring (e.g., formed from a monocyclic or fused ring system), such as substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted cycloalkynyl, or substituted or unsubstituted heterocyclyl having from 3 to 30 carbon atoms (where geometric constraints permit). Substituted cycloalkyl, substituted cycloalkenyl, substituted cycloalkynyl, and substituted heterocyclyl are substituted on alkyl, alkenyl, alkynyl, and heterocyclyl, respectively, as defined (or specified) above.
[0043] The term "aralkyl," as used herein, refers to an aryl or heteroaryl group having an alkyl, alkynyl, or alkenyl group (as defined above) attached to an aromatic group (e.g., aryl, heteroaryl, polyaryl, or polyheteroaryl). An example of an aralkyl group is the benzyl group.
[0044] The terms "alkoxyl" or "alkoxy", "aroxy" or "aryloxy" generally refer to a group of the formula: OR v In the formula, R vExamples of the aryl group include, but are not limited to, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted alkylaryl, substituted or unsubstituted alkylheteroaryl, substituted or unsubstituted aralkyl, substituted or unsubstituted carbonyl, phosphonium, phosphanyl, phosphonyl, sulfinyl, silyl, thiol, amido, and amino. Exemplary alkoxyl groups include methoxy, ethoxy, propyloxy, tert-butoxy, and the like. A "lower alkoxy" group is an alkoxyl group containing 1 to 6 carbon atoms. An "ether" is two functional groups, as defined (or specified) above, covalently linked by an oxygen. Thus, a substituent of an alkyl is one that renders an alkyl ether, and is or resembles an alkoxyl, and can be represented by, for example, one of -O-alkyl, -O-alkenyl, -O-alkynyl, -O-aralkyl, -O-aryl, -O-heteroaryl, -O-polyaryl, -O-polyheteroaryl, -O-heterocyclyl, and the like.
[0045] The term "substituted alkoxy" refers to an alkoxy group having one or more substituents replacing one or more hydrogen atoms on one or more carbons of the alkoxy skeleton (or alkoxy backbone). Such substituents may be any of the substituents described above, including, for example, halogen, azido, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxyl, phosphonium, phosphanyl, phosphoryl, phosphate, phosphonate, phosphinate, amino (e.g., quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, oxo, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof.
[0046] The term "ether," as used in this disclosure, refers to a compound of the formula: 2 Office Automation 1 In the formula, A 2 and A 1 may independently be substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted aralkyl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, phosphonium, phosphanyl, phosphonyl, sulfinyl, silyl, thiol, substituted or unsubstituted carbonyl, alkoxy, amido, or amino (as described above).
[0047] The term "polyether" as used in this disclosure is represented by the formula: [ka] A in the formula 3 may independently be substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted aralkyl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, phosphonium, phosphanyl, substituted or unsubstituted carbonyl, alkoxy, amido, or amino (as described above). g may be a positive integer from 1 to 30.
[0048] The term "phenoxy" is art-recognized and refers to a radical of the formula: v In the formula, R v is C6H5 (i.e., -O-C6H5). One of ordinary skill in the art will recognize that phenoxy is a member of the aroxy family.
[0049] The term "substituted phenoxy" refers to a phenoxy group, as defined (or specified) above, having one or more substituents replacing one or more hydrogen atoms on one or more carbons of the phenyl ring. Such substituents include, but are not limited to, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxyl, phosphonium, phosphanyl, phosphanyl, phosphoryl, phosphate, phosphonate, phosphinate, amino (e.g., quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof.
[0050] The terms "aroxy" and "aryloxy" are used interchangeably in this disclosure and refer to -O-aryl or -O-heteroaryl, where aryl and heteroaryl are as defined in this disclosure.
[0051] The terms "substituted aroxy" and "substituted aryloxy," as used interchangeably in this disclosure, refer to -O-aryl or -O-heteroaryl having one or more substituents replacing one or more hydrogen atoms on one or more ring atoms of the aryl and heteroaryl, as defined (or prescribed) in this disclosure. Such substituents may be any of the substituents described above, such as halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxyl, phosphonium, phosphanyl, phosphoryl, phosphate, phosphonate, phosphinate, amino (e.g., quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, polyaryl, polyheteroaryl, and combinations thereof.
[0052] The term "amino," as used in this disclosure, is intended to include the following groups: [ka] (primary amino), [ka] (secondary amino), [ka] (tertiary amino), and [ka] (Quaternary Amino)
[0053] wherein E is absent, or E is substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl. wherein, independently of E, R x , R xi and R xii are each independently substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbonyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, hydroxyl, alkoxy, phosphonium, phosphanyl, phosphonyl, sulfinyl, silyl, thiol, amido, amino, or -(CH) m -R'''. R''' represents a hydroxyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted polyaryl group, a substituted or unsubstituted polyheteroaryl group, an alkoxy group, a phosphonium group, a phosphanyl group, an amido group, or an amino group. m is zero (0) or an integer ranging from 1 to 8. The term "quaternary amino" also refers to a group consisting of nitrogen, R x , R xi and R xii (These are bonded to N + together with form (or complete) a heterocyclyl or heteroaryl (having 3-14 atoms in the ring structure). One of ordinary skill in the art will appreciate that the E groups listed above are divalent (e.g., methylene, ethane-1,2-diyl, ethene-1,2-diyl, 1,4-phenylene, cyclohexane-1,2-diyl).
[0054] The terms "amide" or "amido" are used interchangeably and refer to both "unsubstituted amides" and "substituted amides" and are represented by the general formula: [ka] or [ka]
[0055] wherein E is absent, or E is substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, or substituted or unsubstituted heterocyclyl. wherein, independent of E, R and R' are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbonyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted arylalkyl), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, hydroxyl, alkoxy, phosphonium, phosphanyl, phosphonyl, sulfinyl, silyl, thiol, amido, amino, or -(CH) m -R'''. Alternatively, R and R', together with the N atom to which they are attached, form (or complete) a heterocycle (or hetero ring or heterocycle) having from 3 to 14 atoms in its ring structure. R''' represents a hydroxyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted polyaryl group, a substituted or unsubstituted polyheteroaryl group, an alkoxy group, a phosphonium group, a phosphanyl group, an amido group, or an amino group. m is zero (0) or an integer ranging from 1 to 8. In some embodiments, when E is oxygen, a carbamate is formed. One of ordinary skill in the art will appreciate that the E groups listed above are divalent (eg, methylene, ethane-1,2-diyl, ethene-1,2-diyl, 1,4-phenylene, cyclohexane-1,2-diyl).
[0056] The term "carbonyl," as used in this disclosure, is art-recognized and includes a moiety that may be represented by the general formula: [ka] or [ka]
[0057] In the formula, X is a bond or represents oxygen or sulfur. R is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbonyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, hydroxyl, alkoxy, phosphonium, phosphanyl, amido, amino, or -(CH) m -R'', or a pharma- ceutically acceptable salt. E" is absent. Alternatively, E" is substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl. R' is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, hydroxyl, alkoxy, phosphonium, phosphanyl, amido, amino, or -(CH) m -R''. R″ represents a hydroxyl group, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, alkoxy, phosphonium, phosphanyl, amido or amino. m is zero (0) or an integer ranging from 1 to 8. Such substituents may be any of those described above, including, for example, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxyl, phosphonium, phosphanyl, phosphoryl, phosphate, phosphonate, phosphinate, amino (e.g., quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof. One of ordinary skill in the art will appreciate that the E'' groups listed above are divalent (eg, methylene, ethane-1,2-diyl, ethene-1,2-diyl, 1,4-phenylene, cyclohexane-1,2-diyl). When X is oxygen and R is as defined above, the moiety is also referred to as a carboxyl group. Where X is an oxygen and R is hydrogen, the formula represents a "carboxylic acid". Where X is an oxygen, and R' is hydrogen, the formula represents a "formate." Where X is an oxygen and R or R' is not hydrogen, the formula represents an "ester". In general, where the oxygen atom of the above formula is replaced with a sulfur atom, the formula represents a "thiocarbonyl group." Where X is a sulfur and R or R' is not hydrogen, the formula represents a "thioester." Where X is a sulfur and R is hydrogen, the formula represents a "thiocarboxylic acid." Where X is a sulfur and R' is hydrogen, the formula represents a "thioformate." Where X is a bond, and R is not hydrogen, the above formula represents a "ketone". Where X is a bond, and R is hydrogen, the above formula represents an "aldehyde."
[0058] The term "phosphanyl" is represented by the formula: [ka]
[0059] wherein E is absent, or E is substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aralkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl. wherein, independently of E, R vi and R viiare each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbonyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, etc.), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, hydroxyl, alkoxy, phosphonium, phosphanyl, phosphonyl, sulfinyl, silyl, thiol, amido, amino, or -(CH) m -R'''. Or, R vi and R vii together with the P atom (or phosphorus atom) to which they are attached form (or complete) a heterocycle (or hetero ring or heterocycle) (having 3-14 atoms in its ring structure). R''' represents a hydroxyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted polyaryl group, a substituted or unsubstituted polyheteroaryl group, an alkoxy group, a phosphonium group, a phosphanyl group, an amido group, or an amino group. m is zero (0) or an integer in the range of 1-8. Such substituents may be any of those described above, including, for example, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxyl, phosphoryl, phosphate, phosphonate, phosphinate, amino (e.g., quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, polyaryl, polyheteroaryl, and combinations thereof. One of ordinary skill in the art will appreciate that the E groups listed above are divalent (eg, methylene, ethane-1,2-diyl, ethene-1,2-diyl, 1,4-phenylene, cyclohexane-1,2-diyl).
[0060] The term "phosphonium" is represented by the formula: [ka]
[0061] wherein E is absent, or E is substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aralkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl. wherein, independently of E, R vi , R vii and R viii are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbonyl, substituted or unsubstituted carbonyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, etc.), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, hydroxyl, alkoxy, phosphonium, phosphanyl, phosphonyl, sulfinyl, silyl, thiol, amido, amino, or -(CH) m -R'''. Or, R vi , R vii and R viii are the P that they combine with + Together with the atom(s) form (or complete) a heterocyclic ring (or heterocycle) (having 3 to 14 atoms in its ring structure). R''' represents a hydroxyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted polyaryl group, a substituted or unsubstituted polyheteroaryl group, an alkoxy group, a phosphonium group, a phosphanyl group, an amido group, or an amino group. m is zero (0) or an integer ranging from 1 to 8. Such substituents may be any of those described above, including, for example, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxyl, phosphoryl, phosphate, phosphonate, phosphinate, amino (e.g., quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, polyaryl, polyheteroaryl, and combinations thereof. One of ordinary skill in the art will appreciate that the E groups listed above are divalent (eg, methylene, ethane-1,2-diyl, ethene-1,2-diyl, 1,4-phenylene, cyclohexane-1,2-diyl).
[0062] The term "phosphonyl" is represented by the formula: [ka]
[0063] wherein E is absent, or E is substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, etc.), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, oxygen, alkoxy, aroxy, or substituted alkoxy or substituted aroxy. wherein, independently of E, R vi and R vii are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbonyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, etc.), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, hydroxyl, alkoxy, phosphonium, phosphanyl, phosphonyl, sulfinyl, silyl, thiol, amido, amino, or -(CH) m -R'''. Or, R vi and R vii together with the P atom (or phosphorus atom) to which they are attached form (or complete) a heterocycle (or hetero ring or heterocycle) (having 3-14 atoms in its ring structure). R''' represents a hydroxyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted polyaryl group, a substituted or unsubstituted polyheteroaryl group, an alkoxy group, a phosphonium group, a phosphanyl group, an amido group, or an amino group. m is zero (0) or an integer in the range of 1-8. Such substituents may be any of those described above, including, for example, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxyl, phosphoryl, phosphate, phosphonate, phosphinate, amino (e.g., quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, polyaryl, polyheteroaryl, and combinations thereof. One of ordinary skill in the art will appreciate that the E groups listed above are divalent (eg, methylene, ethane-1,2-diyl, ethene-1,2-diyl, 1,4-phenylene, cyclohexane-1,2-diyl).
[0064] The term "phosphoryl" refers to phosphonyl where E is absent, oxygen, alkoxy, aroxy, substituted alkoxy, or substituted aroxy, as defined above, and independently of E, R vi and R vii are defined (or specified) as being independently hydroxyl, alkoxy, aroxy, substituted alkoxy or substituted aroxy, as defined (or specified) above. When E is oxygen, phosphoryl cannot be bonded to another chemical species, e.g., cannot be bonded to another chemical species in such a way as to form an oxygen-oxygen bond or other labile bond, as would be understood by one of ordinary skill in the art. E, R vi and R vii When is substituted, the substituents include, but are not limited to, halogen, azido, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxyl, phosphoryl, phosphate, phosphonate, phosphinate, amino (e.g., quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, polyaryl, polyheteroaryl, and combinations thereof. One of ordinary skill in the art will appreciate that the E groups listed above are divalent (eg, methylene, ethane-1,2-diyl, ethene-1,2-diyl, 1,4-phenylene, cyclohexane-1,2-diyl).
[0065] The term "sulfinyl" is represented by the formula: [ka]
[0066] wherein E is absent, or E is substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, etc.), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, or unsubstituted polyheteroaryl. wherein, independently of E, R is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbonyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, hydroxyl, alkoxy, phosphonium, phosphanyl, phosphonyl, silyl, thiol, amido, amino, or -(CH) m -R'''. Alternatively, E and R together with the S atom (or sulfur atom) to which they are attached form (or complete) a heterocycle (or hetero ring or heterocycle) having from 3 to 14 atoms in its ring structure. R''' represents a hydroxyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted polyaryl group, a substituted or unsubstituted polyheteroaryl group, an alkoxy group, a phosphonium group, a phosphanyl group, an amido group, or an amino group. m is zero (0) or an integer in the range of 1-8. Such substituents may be any of those described above, including, for example, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxyl, phosphoryl, phosphate, phosphonate, phosphinate, amino (e.g., quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, polyaryl, polyheteroaryl, and combinations thereof. One of ordinary skill in the art will appreciate that the E groups listed above are divalent (eg, methylene, ethane-1,2-diyl, ethene-1,2-diyl, 1,4-phenylene, cyclohexane-1,2-diyl).
[0067] The term "sulfonyl" is represented by the formula: [ka]
[0068] wherein E is absent, or E is substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, etc.), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, or unsubstituted polyheteroaryl. wherein, independently of E, R is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbonyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, hydroxyl, alkoxy, phosphonium, phosphanyl, amido, amino, or -(CH) m -R'''. Alternatively, E and R together with the S atom (or oxygen atom) to which they are attached form (or complete) a heterocycle (or hetero ring or heterocycle) having from 3 to 14 atoms in its ring structure. R''' represents a hydroxyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted polyaryl group, a substituted or unsubstituted polyheteroaryl group, an alkoxy group, a phosphonium group, a phosphanyl group, an amido group, or an amino group. m is zero (0) or an integer in the range of 1-8. Such substituents may be any of those described above, including, for example, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxyl, phosphoryl, phosphate, phosphonate, phosphinate, amino (e.g., quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, polyaryl, polyheteroaryl, and combinations thereof. One of ordinary skill in the art will appreciate that the E groups listed above are divalent (eg, methylene, ethane-1,2-diyl, ethene-1,2-diyl, 1,4-phenylene, cyclohexane-1,2-diyl).
[0069] The term "sulfonic acid" means sulfonyl (as defined (or specified) above), where R is hydroxyl and E is absent or E is substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, or substituted or unsubstituted heteroaryl. Such substituents may be any of those described above, including, for example, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxyl, phosphoryl, phosphate, phosphonate, phosphinate, amino (e.g., quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, polyaryl, polyheteroaryl, and combinations thereof. One of ordinary skill in the art will appreciate that the E groups listed above are divalent (eg, methylene, ethane-1,2-diyl, ethene-1,2-diyl, 1,4-phenylene, cyclohexane-1,2-diyl).
[0070] The term "sulfate" refers to a sulfonyl (as defined above) where E is absent, oxygen, alkoxy, aroxy, substituted alkoxy, or substituted aroxy (as defined above), and R is independently hydroxyl, alkoxy, aroxy, substituted alkoxy, or substituted aroxy (as defined above). When E is oxygen, the sulfate cannot bond to another chemical species (e.g., cannot bond to another chemical species in a manner that forms an oxygen-oxygen bond or other labile bond). This is understood by those of skill in the art. Such substituents may be any of the substituents described above, including, for example, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxyl, phosphoryl, phosphate, phosphonate, phosphinate, amino (e.g., quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, polyaryl, polyheteroaryl, and combinations thereof. One of ordinary skill in the art will appreciate that the E groups listed above are divalent (eg, methylene, ethane-1,2-diyl, ethene-1,2-diyl, 1,4-phenylene, cyclohexane-1,2-diyl).
[0071] The term "sulfonate" refers to a sulfonyl (as defined or specified above) where E is oxygen, alkoxy, aroxy, substituted alkoxy, or substituted aroxy (as defined or specified above), and R is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted amino, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aralkyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, -(CH) m -R'' means that R''' represents a hydroxy group, a substituted or unsubstituted carbonyl group, an aryl, a cycloalkyl ring, a cycloalkenyl ring, a heterocycle (or heterocyclic ring), an amido, an amino or a polycycle (or polycyclic ring). m is zero (0) or an integer in the range of 1-8. When E is oxygen, the sulfonate cannot be bonded to another chemical species (e.g., cannot be bonded to another chemical species in such a way as to form an oxygen-oxygen bond or other labile bond), as would be understood by one of ordinary skill in the art. Such substituents may be any of those described above, including, for example, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxyl, phosphoryl, phosphate, phosphonate, phosphinate, amino (e.g., quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, polyaryl, polyheteroaryl, and combinations thereof. One of ordinary skill in the art will appreciate that the E groups listed above are divalent (eg, methylene, ethane-1,2-diyl, ethene-1,2-diyl, 1,4-phenylene, cyclohexane-1,2-diyl).
[0072] The term "sulfamoyl" refers to a sulfonamide or a sulfonamide represented by the formula: [ka]
[0073] wherein E is absent, or E is substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted cycloalkyl, etc.), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl. wherein, independent of E, R and R' are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbonyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, etc.), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclyl, hydroxyl, alkoxy, phosphonium, phosphanyl, amido, amino, or -(CH) m -R'''. Alternatively, R and R' together with the N atom (or nitrogen atom) to which they are attached form (or complete) a heterocycle (or hetero ring or heterocycle) having from 3 to 14 atoms in its ring structure. R''' represents a hydroxyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocyclyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted polyaryl group, a substituted or unsubstituted polyheteroaryl group, an alkoxy group, a phosphonium group, a phosphanyl group, an amido group, or an amino group. m is zero (0) or an integer in the range of 1-8. Such substituents may be any of those described above, including, for example, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxyl, phosphoryl, phosphate, phosphonate, phosphinate, amino (e.g., quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, polyaryl, polyheteroaryl, and combinations thereof. One of ordinary skill in the art will appreciate that the E groups listed above are divalent (eg, methylene, ethane-1,2-diyl, ethene-1,2-diyl, 1,4-phenylene, cyclohexane-1,2-diyl).
[0074] The term "silyl group," as used in this disclosure, is represented by the formula: -SiRR'R'', where R, R', and R'' can independently be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted carbonyl, phosphonium, phosphanyl, phosphonyl, sulfinyl, thiol, amido, amino, alkoxy, or oxo, as described above. Such substituents may be any of those described above, including, for example, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxyl, phosphoryl, phosphate, phosphonate, phosphinate, amino (e.g., quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, polyaryl, polyheteroaryl, and combinations thereof.
[0075] The term "thiol" is used interchangeably and is represented by -SR, where R can be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, etc.), substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted carbonyl, phosphonium, phosphanyl, amido, amino, alkoxy, oxo, phosphonyl, sulfinyl, or silyl, as described above. Such substituents may be any of those described above, including, for example, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxyl, phosphoryl, phosphate, phosphonate, phosphinate, amino (e.g., quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, polyaryl, polyheteroaryl, and combinations thereof.
[0076] The disclosed compounds and substituents may independently have two or more of the groups listed above. For example, if the compound or substituent is a straight-chain alkyl group, one of the hydrogen atoms of the alkyl group may be replaced with a hydroxyl group, an alkoxy group, and the like. Depending on the group selected, the first group may be included in the second group. Alternatively, the first group may be pendant (or pendant) to the second group (i.e., bonded to the second group). For example, with respect to the term "alkyl group containing an ester group," the ester group may be included in the skeleton (or backbone) of the alkyl group. Alternatively, the ester may be bonded to the skeleton (or backbone) of the alkyl group. The nature of the group(s) selected will determine whether the first group is included in the second group or the first group is bonded to the second group.
[0077] Compounds and substituents may be independently substituted with the substituents described above in the definition of "substituted."
[0078] Numerical ranges disclose each possible number individually. Such ranges may reasonably encompass any subranges and any combination of subranges contained therein. For example, if a given range is carbon from C3 to C9, the range also discloses C3, C4, C5, C6, C7, C8, C9, and any subranges between these numbers (e.g., C4 to C6), and any possible combination of possible ranges between these values. As yet another example, if a given temperature range may be from about 25°C to about 30°C, the range also discloses temperatures that may be independently selected from about 25, 26, 27, 28, 29, and 30°C, and any ranges between these numbers (e.g., 26 to 28°C), and any possible combination of possible ranges between these values.
[0079] Use of the term "about" is intended to include values above and below the stated value modified by the term "about." The term "about" may be approximately within a range of + / - 10%. When the term "about" is used in front of a numerical range (i.e., about 1-5) or in front of a series of numerical values (i.e., about 1, 2, 3, 4, etc.), it is intended to modify both ends of the numerical range and / or each of the numerical values in the series (unless specifically stated otherwise).
[0080] The disclosed compounds and substituents may independently have two or more of the groups listed above. For example, if the compound or substituent is a straight-chain alkyl group, one of the hydrogen atoms of the alkyl group may be replaced with a hydroxyl group, an alkoxy group, or the like. Depending on the group selected, the first group may be included in the second group. Alternatively, the first group may be pendant (or pendant) to the second group (i.e., bonded to the second group). For example, with respect to the term "alkyl group containing an ester group," the ester group may be included in the skeleton (or backbone) of the alkyl group. Alternatively, the ester may be bonded to the skeleton (or backbone) of the alkyl group. The nature of the group(s) selected will determine whether the first group is included in the second group or the first group is bonded to the second group.
[0081] Compounds and substituents may be independently substituted with the substituents described above in the definition of "substituted."
[0082] II. Composition A class of dinuclear cyclometalated platinum(II) carbene emitter complexes using tridentate CCN ligands is described. The compounds of the present disclosure can be produced by single-step metallation. They preferably have low CIE-y values, down to about 0.07. Without wishing to be bound by theory, it is believed that the increased denticity, relative to monodentate and bidentate ligands, increases device stability by inhibiting or preventing emitter degradation.
[0083] Compounds of the present disclosure have the structure of Formula Ia: [ka] Formula Ia
[0084] During the ceremony The compound has an overall neutral, negative or positive charge.
[0085] A dashed straight line indicates the presence or absence of a bond.
[0086] A and A' are independently selected from substituted cycloalkyl, unsubstituted cycloalkyl, substituted cycloalkenyl, unsubstituted cycloalkenyl, substituted cycloalkynyl, unsubstituted cycloalkynyl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20and C1-C2-C3-C4-C6-C8-C9-, or a fused combination thereof; preferably, A and A' are independently substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyaryl, unsubstituted polyaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C1-C2-C3-C4-C8-C9 ... 20 Heterocyclyl, unsubstituted C1-C 20 heterocyclyl, or a fused combination thereof (or a fused combination thereof).
[0087] X5 and X 5’ are independently carbon or nitrogen and are independently bonded to one or no hydrogen atoms depending on the valency. Preferably, X and X 5’ is carbon.
[0088] R5, R6, R 5’ and R 6’is independently absent, hydrogen, substituted alkyl, unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, substituted aryl, unsubstituted aryl, halogen, hydroxyl, thiol, cyano, nitro-, unsubstituted alkoxy, substituted alkoxy, unsubstituted aroxy, substituted aroxy, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, unsubstituted alkylthio, substituted alkylthio, unsubstituted carbonyl, substituted carbonyl, unsubstituted carboxyl, substituted carboxyl, unsubstituted ester, substituted ester, substituted C-C 20 Cycloalkyl, unsubstituted C3-C 20 Cycloalkyl, Substituted C1-C 20 Heterocyclyl, unsubstituted C1-C 20 Heterocyclyl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 Cycloalkenyl, substituted C3-C 20 Cycloalkynyl, unsubstituted C3-C 20 cycloalkynyl; or R5, R6, R 5’ and R 6’ together with the atom to which they are attached, represent substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 Preferably, R, R, R 5’ and R 6’ is independently absent, hydrogen, substituted alkyl, unsubstituted alkyl, substituted aryl, or unsubstituted aryl.
[0089] A1, A2, A3, A4, A 1’, A 2’ , A 3’ and A 4’ is independently absent, hydrogen, deuterium, carbon, nitrogen, unsubstituted aryl or substituted aryl, and, if present, is independently bonded to 1, 2, 3, 4, 5, or no hydrogen atoms, depending on the valency.
[0090] R 1a , R 2a , R 3a , R 4a , R 1a’ , R 2a’ , R 3a’ and R 4a’ is independently absent, hydrogen, deuterium, substituted alkyl, unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, substituted aryl, unsubstituted aryl, halogen, hydroxyl, thiol, cyano, nitro-, unsubstituted alkoxy, substituted alkoxy, unsubstituted aroxy, substituted aroxy, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, unsubstituted alkylthio, substituted alkylthio, unsubstituted carbonyl, substituted carbonyl, unsubstituted carboxyl, substituted carboxyl, unsubstituted ester, substituted ester, substituted C-C 20 Cycloalkyl, unsubstituted C3-C 20 Cycloalkyl, Substituted C1-C 20 Heterocyclyl, unsubstituted C1-C 20 Heterocyclyl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 Cycloalkenyl, substituted C3-C 20 Cycloalkynyl, unsubstituted C3-C 20cycloalkynyl, fused combinations thereof (or fused combinations thereof) (e.g., dibenzofuran-4-yl, dibenzofuran-3-yl, dibenzothiopen-4-yl, dibenzothiopen-3-yl, etc.), or R 1a and R 2a , R 2a and R 3a , R 3a and R 4a , R 1a’ and R 2a’ , R 2a’ and R 3a’ , R 3a’ and R 4a’ or combinations thereof, together with the atom to which they are attached, are substituted cycloalkyl, unsubstituted cycloalkyl, substituted cycloalkenyl, unsubstituted cycloalkenyl, substituted cycloalkynyl, unsubstituted cycloalkynyl, substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyaryl, unsubstituted polyaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 heterocyclyl, a fused combination thereof (or a fused combination thereof), or R 1a and R 2a , R 2a and R 3a , R 3a and R 4a , R 1a’ and R 2a’ , R 2a’ and R 3a’ , R 3a’ and R 4a’ or any combination thereof, taken together with the atom to which they are attached, is substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyaryl, unsubstituted polyaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C-C 20Heterocyclyl, unsubstituted C1-C 20 heterocyclyl, which form fused combinations (or combinations thereof which are fused).
[0091] L1 and L 1’ are independently substituted alkyl, unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, unsubstituted alkoxy, substituted alkoxy, unsubstituted aroxy, substituted aroxy, unsubstituted alkylthio, substituted alkylthio, unsubstituted carbonyl, substituted carbonyl, unsubstituted carboxyl, substituted carboxyl, unsubstituted ester, substituted ester, unsubstituted ether, substituted ether, unsubstituted polyether, substituted polyether, substituted amino, unsubstituted amino, substituted amido, unsubstituted amido, substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyaryl, unsubstituted polyaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C3-C 20 Cycloalkyl, unsubstituted C3-C 20 Cycloalkyl, Substituted C1-C 20 Heterocyclyl, unsubstituted C1-C 20 Heterocyclyl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 Cycloalkenyl, substituted C3-C 20 Cycloalkynyl, unsubstituted C3-C 20 cycloalkynyl, or a fused combination thereof (or a fused combination thereof). In some embodiments, L and L 1’ is independently substituted or unsubstituted alkyl. In some embodiments, L and L1’ are independently substituted C1-C 10 Alkyl or unsubstituted C1-C 10 It is an alkyl. In some embodiments, L and L 1’ are independently substituted C2-C 10 Alkyl or unsubstituted C2-C 10 It is an alkyl. L1 and L 1’ In some embodiments, substituted alkyl, substituted C-C 10 Alkyl or substituted C2-C 10 An alkyl group can have one or more alkyl substituents (e.g., methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl), one or more ether linkages, one or more amine groups (e.g., substituted or unsubstituted amines), one or more substituted aryl groups, one or more substituted heteroaryl groups, one or more substituted C-C 20 Cycloalkyl groups, one or more substituted C1-C 20 or combinations thereof. In some embodiments, the compounds are fluorine-free (or fluorine-free), i.e., they are not covalently bonded to fluorine atoms. L1 and L 1’ It should be understood that is at least divalent. Without wishing to be bound by theory, fluorine-containing emitter complexes (or fluorine-containing emitter complexes) have poor thermal and electrochemical stability. For example, during the sublimation process, fluorine cleavage occurs. This means that the stability of fluorine-containing emitters in electroluminescent devices may be reduced, i.e. the lifetime of the device may be shortened.
[0092] In some embodiments, the compound is as described above for formula Ia, except that the compound has the structure of formula IIa or IIb:
[0093] [ka] Formula IIa or [ka] Formula IIb
[0094] During the ceremony A dashed straight line indicates the presence or absence of a bond. (i) A1, A2, A3, A4, A 1’ , A 2’ , A 3’ and A 4’ (ii)R 1a , R 2a , R 3a , R 4a , R 1a’ , R 2a’ , R 3a’ and R 4a’ (iii) L1 and L 1’ , and (iv) X5, X 5’ , R5, R6, R 5’ and R 6’ is as described above for formula Ia.
[0095] X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X4’ is independently carbon, nitrogen, oxygen, or sulfur, if present, and is independently bonded to one hydrogen atom or to no hydrogen atoms, depending on the valency.
[0096] R1, R2, R3, R4, R 1’ , R 2’ , R 3’ and R 4’ is independently absent, deuterium, hydrogen, substituted alkyl (e.g., trifluoromethyl), unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, substituted aryl (e.g., mesityl (2,4,6-trimethylphenyl), 3,5-di-tert-butylphenyl, 2,6-dimethylphenyl), unsubstituted aryl, halogen (e.g., fluorine), hydroxyl, thiol, cyano, nitro-, unsubstituted alkoxy, substituted alkoxy, unsubstituted aroxy, substituted aroxy, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, unsubstituted alkylthio, substituted alkylthio, unsubstituted carbonyl, substituted carbonyl, unsubstituted carboxyl, substituted carboxyl, unsubstituted ester, substituted ester, substituted C-C 20 Cycloalkyl, unsubstituted C3-C 20 Cycloalkyl, Substituted C1-C 20 Heterocyclyl, unsubstituted C1-C 20 Heterocyclyl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 Cycloalkenyl, substituted C3-C 20 Cycloalkynyl or unsubstituted C3-C 20 cycloalkynyl. Alternatively, R1 and R2, R2 and R3, R3 and R4, R 1’ and R 2’ , R 2’ and R3’ , R 3’ and R 4’ or combinations thereof, together with the atom to which they are attached, are substituted cycloalkyl, unsubstituted cycloalkyl, substituted cycloalkenyl, unsubstituted cycloalkenyl, substituted cycloalkynyl, unsubstituted cycloalkynyl, substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyaryl, unsubstituted polyaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 heterocyclyl, or a fused combination thereof (or a fused combination thereof). In some embodiments, R1, R2, R3, R4, R 1’ , R 2’ , R 3’ and R 4’ are independently absent, hydrogen, deuterium, substituted alkyl (e.g., trifluoromethyl), unsubstituted alkyl, substituted aryl (e.g., mesityl (2,4,6-trimethylphenyl), 3,5-di-tert-butylphenyl, 2,6-dimethylphenyl), unsubstituted aryl, halogen (e.g., fluorine). Alternatively, R1 and R2, R2 and R3, R3 and R4, R 1’ and R 2’ , R 2’ and R 3’ , R 3’ and R 4’ or any combination thereof, together with the atom to which they are attached, represents substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 heterocyclyl, or a fused combination thereof (or a fused combination thereof).
[0097] In some embodiments, the compound is as described above for Formula Ia, Formula IIa, or Formula IIb, except that the compound has the structure of Formula IIIa or Formula IIIb.
[0098] [ka] Formula IIIa or [ka] Formula IIIb
[0099] During the ceremony A dashed straight line indicates the presence or absence of a bond.
[0100] A5, A6, A 5’ and A 6’ are independently hydrogen, deuterium, unsubstituted alkyl, substituted alkyl, substituted aryl, unsubstituted aryl, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, substituted C-C 20 Heterocyclyl or unsubstituted C1-C 20 heterocyclyl; or, preferably, hydrogen, unsubstituted alkyl, substituted alkyl, deuterium, substituted aryl, or unsubstituted aryl. In some forms, A5, A6, A 5’ and A 6’ is hydrogen or deuterium. 5’ and A 6’ is an unsubstituted alkyl (e.g., unsubstituted C-C 10 alkyl, unsubstituted C1-C5 alkyl, or unsubstituted C1-C3 alkyl) or substituted alkyl (e.g., substituted C1-C 10 alkyl, substituted C1-C5 alkyl, or substituted C1-C3 alkyl). In some forms, A5, A6, A 5’ and A 6’ is hydrogen, substituted aryl, or unsubstituted aryl, provided that at least one of A5 and A6, or A 5’ and A 6’ At least one of is substituted or unsubstituted aryl.
[0101] In some embodiments, the compound is as described above for Formula IIa or Formula IIIa, except that X1, X2, X3, X4, X5, X6, X7, X8, X9, X10, X111, X12, X13, X14, X15, X16, X17, X18, X19, X20, X21, X22, X23, X24, X25, X30, X31, X32, X3 1’ , X 2’ , X 3’ and X 4’ is a carbon and is independently bonded to one or no hydrogen atoms, depending on the valency.
[0102] In some embodiments, the compound is as described above for Formula IIa or Formula IIIa, except that one or more of X1, X2, X3, X4, and one or more of X 1’ , X 2’ , X 3’ and X 4’ is nitrogen, and X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X 4’ are independently bonded to one hydrogen atom or to no hydrogen atoms, depending on the valency. In some embodiments, the compound is as described above for Formula IIa or Formula IIIa, except that X and X 2’ is nitrogen, and X1, X3, X4, X 1’ , X 3’ and X 4’ is carbon, and X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X 4’are independently bonded to one hydrogen atom or to no hydrogen atoms, depending on the valency.
[0103] In some embodiments, the compound is as described above for Formula IIa or Formula IIIa, except that R1, R2, R3, R4, R 1’ , R 2’ , R 3’ and R 4’ are independently absent, hydrogen, deuterium, substituted alkyl (e.g., trifluoromethyl), unsubstituted alkyl, substituted aryl (e.g., mesityl (2,4,6-trimethylphenyl), 3,5-di-tert-butylphenyl, 2,6-dimethylphenyl), unsubstituted aryl, halogen (e.g., fluorine). Alternatively, R1 and R2, R2 and R3, R3 and R4, R 1’ and R 2’ , R 2’ and R 3’ , R 3’ and R 4’ or any combination thereof, together with the atom to which they are attached, represents substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 heterocyclyl, or a fused combination thereof (or a fused combination thereof).
[0104] In some embodiments, the compound is as described above for Formula IIa or Formula IIIa, except that R1, R2, R3, R4, R 1’ , R 2’ , R 3’ and R 4’is independently absent, hydrogen, deuterium, substituted alkyl (e.g., trifluoromethyl), unsubstituted alkyl, substituted aryl (e.g., mesityl (2,4,6-trimethylphenyl), 3,5-di-tert-butylphenyl, 2,6-dimethylphenyl), unsubstituted aryl, or halogen (e.g., fluorine).
[0105] In some embodiments, the compound is as described above for Formula IIa or Formula IIIa, except that R1 and R2, R2 and R3, R3 and R4, R 1’ and R 2’ , R 2’ and R 3’ , R 3’ and R 4’ or any combination thereof, together with the atom to which they are attached, represents substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 heterocyclyl, or a fused combination thereof (or a fused combination thereof). In some embodiments, R1 and R2, R2 and R3, R3 and R4, R 1’ and R 2’ , R 2’ and R 3’ , R 3’ and R 4’ or combinations thereof, together with the atoms to which they are attached, form: [ka] or [ka]
[0106] During the ceremony Q5 is NR 14 , carbon, or sulfur, or oxygen. 10 ~R 14are independently selected from the group consisting of hydrogen, substituted alkyl, unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, substituted aryl, unsubstituted aryl, halogen, hydroxyl, amino, amido, ether, thiol, cyano, nitro, unsubstituted alkoxy, substituted alkoxy, unsubstituted aroxy, substituted aroxy, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, unsubstituted carbonyl, substituted carbonyl, unsubstituted ester, substituted ester, substituted C-C 20 Heterocyclyl or unsubstituted C1-C 20 It may be a heterocyclyl. In some embodiments, Q5 is NR 14 , carbon, or sulfur, or oxygen, e.g., oxygen. 10 ~R 14 is independently may be absent, may be hydrogen, substituted alkyl, or unsubstituted alkyl. In some embodiments, Q5 can be oxygen. 10 ~R 14 may be hydrogen.
[0107] In some embodiments, the compound is as described above for Formula IIb or Formula IIIb, except that one or more of X1, X2, and X3, and one or more of X 1’ , X 2’ and X 3’ is sulfur, oxygen or nitrogen, and X1, X2, X3, X 1’ , X 2’ and X 3’ are independently bonded to one hydrogen atom or to no hydrogen atoms, depending on the valency. In some embodiments, the compound is as described above for Formula IIb or Formula IIIb, except that one or more of X1, X2, and X3, and one or more of X 1’ , X 2’ and X 3’ is sulfur, and X1, X2, X3, X 1’ , X 2’ and X 3’ are independently bonded to one hydrogen atom or to no hydrogen atoms, depending on the valency. In some embodiments, the compound is as described above for Formula IIb or Formula IIIb, except that one of X1, X2, and X3, X 1’ , X 2’ and X 3’ One of them is sulfur, and the other is X1, X2, X3, and X 1’ , X 2’ and X 3’ are independently bonded to one hydrogen atom or to no hydrogen atoms, depending on the valency.
[0108] In some embodiments, the compound is as described above for Formula IIb or Formula IIIb, except that one or more of X1, X2, and X3, and one or more of X 1’ , X 2’ and X 3’ is oxygen, and X1, X2, X3, X 1’ , X 2’ and X 3’ are independently bonded to one hydrogen atom or to no hydrogen atoms, depending on the valency. In some embodiments, the compound is as described above for Formula IIb or Formula IIIb, except that one of X1, X2, and X3, and X 1’ , X 2’ and X 3’ One of the is oxygen, and X1, X2, X3, X 1’ , X 2’ and X 3’are independently bonded to one hydrogen atom or to no hydrogen atoms, depending on the valency.
[0109] In some embodiments, the compound is as described above for Formula IIb or Formula IIIb, except that R1, R2, R3, R 1’ , R 2’ and R 3’ are independently absent, hydrogen, substituted alkyl, unsubstituted alkyl, substituted aryl, unsubstituted aryl, or halogen. Alternatively, R1 and R2, R2 and R3, R 1’ and R 2’ , R 2’ and R 3’ or any combination thereof, together with the atom to which they are attached, represents substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 heterocyclyl, or a fused combination thereof (or a fused combination thereof).
[0110] In some embodiments, the compound is as described above for Formula IIb or Formula IIIb, except that R1, R2, R3, R 1’ , R 2’ and R 3’ is hydrogen, substituted alkyl, unsubstituted alkyl, substituted aryl, unsubstituted aryl, halogen. In some embodiments, the compound is as described above for Formula IIb or Formula IIIb, except that R1, R2, R3, R 1’ , R 2’ and R 3’ is absent, hydrogen, or a combination thereof.
[0111] In some embodiments, the compound is as described above for Formula IIb or Formula IIIb, except that R1 and R2, R2 and R3, R 1’ and R 2’ , R 2’ and R 3’ or any combination thereof, together with the atom to which they are attached, represents substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 heterocyclyl, or a fused combination thereof (or a fused combination thereof). In some embodiments, the compound is as described above for Formula IIb or Formula IIIb, except that R1 and R2, R2 and R3, R 1’ and R 2’ , R 2’ and R 3’ or combinations thereof, together with the atoms to which they are attached, form: [ka] or [ka]
[0112] During the ceremony Q5 is NR 14 , carbon, or sulfur, or oxygen. 10 ~R 14are independently selected from the group consisting of hydrogen, substituted alkyl, unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, substituted aryl, unsubstituted aryl, halogen, hydroxyl, amino, amido, ether, thiol, cyano, nitro, unsubstituted alkoxy, substituted alkoxy, unsubstituted aroxy, substituted aroxy, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, unsubstituted carbonyl, substituted carbonyl, unsubstituted ester, substituted ester, substituted C-C 20 Heterocyclyl or unsubstituted C1-C 20 It may be a heterocyclyl. In some embodiments, Q5 is NR 14 , carbon, or sulfur, or oxygen, e.g., sulfur. R 10 ~R 14 is independently may be absent, may be hydrogen, substituted alkyl, or unsubstituted alkyl. In some embodiments, Q5 can be sulfur. 10 ~R 14 may be hydrogen.
[0113] In some embodiments, the compound is as described above for Formula Ia, Formula IIa, or Formula IIb, except that the compound has the structure of Formula IVa or IVb: [ka] Formula IVa or [ka] Formula IVb
[0114] During the ceremony A dashed straight line indicates the presence or absence of a bond. (i) R 1a , R 2a , R 3a , R 4a , R 1a’ , R 2a’ , R 3a’ and R 4a’ (ii) L1 and L 1’ , and (iii) X5, X 5’ , R5, R6, R 5’ and R 6’ is as described above for formula Ia.
[0115] A1, A2, A3, A4, A 1’ , A 2’ , A 3’ and A 4’ are independently carbon, nitrogen, oxygen, or sulfur and are independently bonded to one hydrogen atom or to no hydrogen atoms, depending on the valency.
[0116] X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X 4’ is independently carbon, nitrogen, oxygen, or sulfur, if present, and is independently bonded to one hydrogen atom or to no hydrogen atoms, depending on the valency.
[0117] R1, R2, R3, R4, R 1’ , R 2’ , R 3’ and R 4’is independently absent, hydrogen, deuterium, substituted alkyl, unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, substituted aryl (e.g., mesityl (2,4,6-trimethylphenyl), 3,5-di-tert-butylphenyl, 2,6-dimethylphenyl), unsubstituted aryl, halogen (e.g., fluorine), hydroxyl, thiol, cyano, nitro-, unsubstituted alkoxy, substituted alkoxy, unsubstituted aroxy, substituted aroxy, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, unsubstituted alkylthio, substituted alkylthio, unsubstituted carbonyl, substituted carbonyl, unsubstituted carboxyl, substituted carboxyl, unsubstituted ester, substituted ester, substituted C-C 20 Cycloalkyl, unsubstituted C3-C 20 Cycloalkyl, Substituted C1-C 20 Heterocyclyl, unsubstituted C1-C 20 Heterocyclyl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 Cycloalkenyl, substituted C3-C 20 Cycloalkynyl or unsubstituted C3-C 20 cycloalkynyl. Alternatively, R1 and R2, R2 and R3, R3 and R4, R 1’ and R 2’ , R 2’ and R 3’ , R 3’ and R 4’or combinations thereof, together with the atom to which they are attached, are substituted cycloalkyl, unsubstituted cycloalkyl, substituted cycloalkenyl, unsubstituted cycloalkenyl, substituted cycloalkynyl, unsubstituted cycloalkynyl, substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyaryl, unsubstituted polyaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 heterocyclyl, or a fused combination thereof (or a fused combination thereof). In some embodiments, R1, R2, R3, R4, R 1’ , R 2’ , R 3’ and R 4’ are independently absent, hydrogen, deuterium, substituted alkyl, unsubstituted alkyl, substituted aryl (e.g., mesityl (2,4,6-trimethylphenyl), 3,5-di-tert-butylphenyl, 2,6-dimethylphenyl), unsubstituted aryl, halogen (e.g., fluorine). Alternatively, R1 and R2, R2 and R3, R3 and R4, R 1’ and R 2’ , R 2’ and R 3’ , R 3’ and R 4’ or any combination thereof, taken together with the atom to which they are attached, is substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyaryl, unsubstituted polyaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 heterocyclyl, or a fused combination thereof (or a fused combination thereof). In some embodiments, R1, R2, R3, R4, R1’ , R 2’ , R 3’ and R 4’ is independently absent, hydrogen, deuterium, substituted alkyl, unsubstituted alkyl, substituted aryl (e.g., mesityl (2,4,6-trimethylphenyl), 3,5-di-tert-butylphenyl, 2,6-dimethylphenyl), unsubstituted aryl, halogen (e.g., fluorine).
[0118] In some embodiments, the compound is as described above for Formula Ia, Formula IIa, or Formula IVa, except that A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A 1’ , A 2’ , A 3’ and A 4’ are carbons, which are independently bonded to one or no hydrogen atoms, depending on the valency. X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X 4’ is a carbon and is independently bonded to one or no hydrogen atoms, depending on the valency. In some embodiments, R1, R2, R3, R4, R 1’ , R 2’ , R 3’ and R 4’ is independently absent, hydrogen, substituted alkyl, unsubstituted alkyl, substituted aryl, unsubstituted aryl, or halogen. In some forms, R 1a , R 2a , R 3a , R 4a , R 1a’ , R 2a’ , R 3a’ and R 4a’ are independently absent, hydrogen, deuterium, substituted alkyl, unsubstituted alkyl, substituted aryl, or unsubstituted aryl; 1a and R 2a, R 2a and R 3a , R 3a and R 4a , R 1a’ and R 2a’ , R 2a’ and R 3a’ , R 3a’ and R 4a’ or any combination thereof, together with the atom to which they are attached, form a substituted or unsubstituted aryl. In some forms, R 1a and R 2a , R 3a and R 4a , R 1a’ and R 2a’ , R 3a’ and R 4a’ together with the atom to which they are attached form a substituted or unsubstituted aryl.
[0119] In some embodiments, the compound is as described above for Formula Ia, Formula IIa, or Formula IVa, except that one or more of A1, A2, A3, and A4 are oxygen, nitrogen, or sulfur, and one or more of A 1’ , A 2’ , A 3’ and A 4’ is oxygen, nitrogen or sulfur. A1, A2, A3, A4, A 1’ , A 2’ , A 3’ and A 4’ are independently bonded to one hydrogen atom or not bonded to a hydrogen atom, depending on the valency. X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X 4’ is a carbon and is independently bonded to one or no hydrogen atoms, depending on the valency. In some embodiments, R1, R2, R3, R4, R 1’ , R 2’ , R 3’ and R 4’is independently absent, hydrogen, deuterium, substituted alkyl, unsubstituted alkyl, substituted aryl (e.g., mesityl (2,4,6-trimethylphenyl), 3,5-di-tert-butylphenyl, 2,6-dimethylphenyl), unsubstituted aryl, or halogen (e.g., fluorine). In some forms, R 1a , R 2a , R 3a , R 4a , R 1a’ , R 2a’ , R 3a’ and R 4a’ is independently absent, hydrogen, deuterium, substituted alkyl, unsubstituted alkyl, substituted aryl, or unsubstituted aryl (e.g., phenyl).
[0120] In some embodiments, the compound is as described above for Formula Ia, Formula IIa, or Formula IVa, except that one or more of A1, A2, A3, and A4 are nitrogen. 1’ , A 2’ , A 3’ and A 4’ is nitrogen. A1, A2, A3, A4, A 1’ , A 2’ , A 3’ and A 4’ are independently bonded to one hydrogen atom or not bonded to a hydrogen atom, depending on the valency. X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X 4’ is a carbon and is independently bonded to one or no hydrogen atoms, depending on the valency. In some embodiments, the compound is as described above for Formula Ia, Formula IIa, or Formula IVa, except that one of A1, A2, A3, and A4 is nitrogen and the other three are carbon. 1’ , A 2’ , A 3’ and A4’ One of them is nitrogen and the other three are carbon. A1, A2, A3, A4, A 1’ , A 2’ , A 3’ and A 4’ are independently bonded to one hydrogen atom or not bonded to a hydrogen atom, depending on the valency. X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X 4’ is a carbon and is independently bonded to one or no hydrogen atoms, depending on the valency. In some embodiments, the compound is as described above for Formula Ia, Formula IIa, or Formula IVa, except that two of A1, A2, A3, and A4 are nitrogen and the other two are carbon. 1’ , A 2’ , A 3’ and A 4’ Two of them are nitrogen and the other two are carbon. A1, A2, A3, A4, A 1’ , A 2’ , A 3’ and A 4’ are independently bonded to one hydrogen atom or not bonded to a hydrogen atom, depending on the valency. X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X 4’ is a carbon and is independently bonded to one or no hydrogen atoms, depending on the valency.
[0121] In some embodiments, the compound is as described above for Formula Ia, Formula IIa, or Formula IVa, except that one or more of A1, A2, A3, and A4 are oxygen, nitrogen, or sulfur, and one or more of A 1’ , A 2’ , A 3’ and A 4’ is nitrogen or sulfur. A1, A2, A3, A4, A1’ , A 2’ , A 3’ and A 4’ are independently bonded to one hydrogen atom or not bonded to a hydrogen atom, depending on the valency. 1’ , X 2’ , X 3’ and X 4’ X1, X2, X3, X4, X are oxygen, nitrogen or sulfur. 1’ , X 2’ , X 3’ and X 4’ are independently bonded to one hydrogen atom or to no hydrogen atoms, depending on the valency. In some embodiments, R1, R2, R3, R4, R 1’ , R 2’ , R 3’ and R 4’ is independently absent, hydrogen, substituted alkyl, unsubstituted alkyl, substituted aryl, unsubstituted aryl, or halogen (e.g., fluorine). 1a , R 2a , R 3a , R 4a , R 1a’ , R 2a’ , R 3a’ and R 4a’ is independently absent, hydrogen, substituted alkyl, unsubstituted alkyl, substituted aryl, or unsubstituted aryl.
[0122] In some embodiments, the compound is as described above for Formula Ia, Formula IIa, or Formula IVa, except that one or more of A1, A2, A3, and A4 are nitrogen. 1’ , A 2’ , A 3’ and A 4’ is nitrogen. A1, A2, A3, A4, A 1’ , A 2’ , A 3’ and A 4’are independently bonded to one hydrogen atom or not bonded to a hydrogen atom, depending on the valency. 1’ , X 2’ , X 3’ and X 4’ is nitrogen. X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X 4’ are independently bonded to one hydrogen atom or to no hydrogen atoms, depending on the valency. In some embodiments, the compound is as described above for Formula Ia, Formula IIa, or Formula IVa, except that one of A1, A2, A3, and A4 is nitrogen and the other three are carbon. 1’ , A 2’ , A 3’ and A 4’ One of them is nitrogen and the other three are carbon. A1, A2, A3, A4, A 1’ , A 2’ , A 3’ and A 4’ are independently bonded to one hydrogen atom or not bonded to a hydrogen atom, depending on the valency. One of X1, X2, X3 and X4 is nitrogen and the other three are carbon. X 1’ , X 2’ , X 3’ and X 4’ One of the atoms is nitrogen and the other three are carbon. X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X 4’ are independently bonded to one hydrogen atom or to no hydrogen atoms, depending on the valency.
[0123] In some embodiments, the compound has a structure selected from the following: [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0124] III. Manufacturing method and reagents therefor A. Emitter Platinum(II) Dinuclear Complexes The emitter platinum(II) dinuclear complexes and ligands described in this disclosure can be synthesized using methods known in the art of organic chemical synthesis. For example, the ligands can be purchased from commercial chemical manufacturers. Alternatively, they can be prepared according to procedures described in the literature and / or adapted from the literature. The selection of appropriate synthesis conditions, reagents, reaction work-up conditions, and purification techniques (if necessary) are known to those skilled in the art of synthesis. Exemplary non-limiting syntheses of ligands and emitter platinum(II) dinuclear complexes are discussed in the following examples.
[0125] B. Ligand Synthetic methods for preparing the ligands of the compounds described above are known from the literature or may be adapted from the literature. In some cases, the pyrazole and triazole ligands described in this disclosure and used in the following examples can be readily obtained from commercial chemical manufacturers. Exemplary syntheses of NHC ligands and bridge ligands (or bridge ligands or bridging ligands) are described in the following examples.
[0126] C. Organic Light Emitting Devices Also described are methods of fabricating organic light-emitting devices (e.g., OLEDs) that include one or more of the emitter platinum(II) dinuclear complexes described above. In some embodiments, the OLEDs can be prepared by vacuum deposition or solution processing techniques (e.g., spin coating and ink printing (e.g., ink jet printing or roll-to-roll printing). Exemplary, non-limiting methods of fabricating OLEDs that include one or more of the emitter platinum(II) dinuclear complexes described in this disclosure are described in the Examples.
[0127] Non-specific tridentate ligands are generally known in the art. On the other hand, metal complexes formed from tridentate ligands are typically, most commonly, mononuclear. It is not straightforward to obtain dinuclear metal complexes, especially from methods used to form mononuclear complexes. Furthermore, changing the denticity of the ligands from bidentate to tridentate can induce structural distortions in the metal complexes, thus resulting in unknown photophysical properties. Furthermore, methods must be developed to synthesize tridentate ligands.
[0128] IV.How to use Preferably, the emitter platinum(II) binuclear complexes described in this disclosure are photostable, thermostable and / or luminescent (or irradiatable) at room temperature, low temperature, or a combination thereof. Thus, the complexes can be incorporated into organic electronic components, including, but not limited to, OLEDs or electrochemiluminescent cells (or light-emitting electrochemical cells) (LEECs). Such OLEDs can be used in commercial applications.For example, smart phones, televisions, monitors, digital cameras, tablet computers, lighting fixtures that normally operate at room temperature, fixed visual display units, mobile visual display units, illumination units, keyboards, clothes, ornaments, garment accessories, wearable devices, medical monitoring devices, wallpaper, tablet PCs, laptops, advertisement panels, panel display units, and the like. Examples of appliances include home electronics, home electronics, office electronics, and home electronics.
[0129] In some forms of organic electronic components, the compound is in (or is included in) an emissive layer. In some embodiments, the compound further comprises a pure organic emitter in (or included in) the light-emitting layer. In such a form, the compound can act as a sensitizer (or sensitizer) to transfer (or transport or transfer) energy to a pure organic emitter. In such a form, the compound can have a higher-lying singlet state than a pure organic emitter. The term "pure organic emitter" as used throughout this application means light-emitting organic molecules formed exclusively from main group elements of the periodic table such that such light-emitting organic molecules do not contain covalent or coordinate bonds to main group metals. In particular, the term is not intended to define or specify a level of purity of a composition that includes light-emitting organic molecules. In some embodiments, the organic electronic component comprises an anode, a cathode, a hole transport region, and an electron transport region. In some embodiments, the hole transport region comprises a hole injection layer (or hole injection layer or hole injection layer) and / or a hole transport layer (or hole transport layer or hole transport layer) and, optionally, an electron blocking layer (or electron blocking layer or electron blocking layer). In some embodiments, the electron transport region includes an electron transport layer (or electron transport layer) and / or an electron injection layer (or electron injection layer), and optionally a hole blocking layer (or hole blocking layer or hole blocking layer or hole blocking layer). In some embodiments, the light-emitting layer is disposed between the anode and the cathode. In some embodiments, the hole transport region is disposed between the anode and the light-emitting layer. In some embodiments, the electron transport region is disposed between the cathode and the light-emitting layer.
[0130] Methods for preparing OLEDs that include one or more emitter platinum(II) dinuclear complexes (as described above) are well known in the field of organic electronics. Such methods for manufacturing OLEDs may include vacuum deposition or solution processing techniques (e.g., spin coating and ink jet printing). The selection of appropriate materials (anode, cathode, hole transport layer, electron transport layer, etc.), fabrication parameters (e.g., deposition conditions or solution selection) necessary to fabricate OLEDs containing the emitter platinum(II) dinuclear complexes described in this disclosure are known in the art.
[0131] In one non-limiting example, an organic light emitting device can have an ordered structure, including at least an anode, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode, where the light emitting layer includes an emitter platinum(II) dinuclear complex (as described above). According to FIG. 2, an organic light emitting device (OLED) 100 can include the following (i) to (vi): (i) a cathode 110 (preferably including an aluminum layer 120 and a lithium layer 130); (ii) an optional electron transport layer 140; (iii) an optional carrier confinement layer 150; (iv) light-emitting layer 160 (comprising an emitter platinum(II) dinuclear complex described in this disclosure); (v) an optional hole transport layer 170; and (vi) Anode 180 (e.g., indium tin oxide coated glass) Flexible substrates (or gases) (or flexible substrates or flexible substrates) other than glass (eg, plastic substrates) are also known in the art. The above are non-limiting examples of OLED devices that can be made. It will be understood that a variety of other OLED constructions (or architectures) are possible.
[0132] The light-emitting layer (or light-emitter layer or light-emitting layer) can be formed by doping an emitter platinum (II) binuclear complex as a dopant into a host compound (or host compound). The light-emitting compound (or luminescent compound) has a percentage composition (or percent composition or percent composition) of about 3% by weight (wt / wt%) to about 20% by weight (wt / wt%), for example about 4% by weight to about 16% by weight, for example about 4% by weight, about 8% by weight, about 16% by weight. In some embodiments, the light-emitting layer has a thickness of about 5 nm to about 120 nm, about 5 nm to about 60 nm, for example about 10 nm to about 60 nm.
[0133] In some embodiments, the light-emitting layer (or light-emitting layer or light-emitting layer) comprises a host compound. The host compound can be 1,3-bis(N-carbazolyl)benzene (mCP), 4,4'-bis(carbazol-9-yl)biphenyl (CBP), 4,4',4''-tris(carbazol-9-yl)-triphenylamine (TCTA), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,butylphenyl-1,2,4-triazole (TAZ), p-bis(triphenylsilyl)benzene (UGH2), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), bis-4-(N The host may be selected from, but is not limited to, diphenyl-4-triphenylsilylphenyl-phosphine oxide (TSPO1), 2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan (PPF), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 3,3'-di(9H-carbazol-9-yl)-1,1'-biphenyl (mCBP), poly(methyl methacrylate) (PMMA), polystyrene (PS), and suitable combinations thereof. For example, in some embodiments, two hosts, such as CzSi:TSPO1, BCPO:TSPO1, BCPO:CzSi, may be used in a suitable relative ratio. Exemplary relative molar ratios of the two hosts may range from about 0.5:1 to 2:1.
[0134] In some embodiments, the hole transport layer (or hole transport layer or hole transport layer or hole transport layer or hole transporting layer) comprises an organic compound. The organic compound can include, but is not limited to, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), 4,4'-bis[N-(3-methylphenyl)-N-phenylamino]biphenyl (TPD), 4,4',4''-tris[(3-methylphenyl)phenylamino]triphenylamine (MTDATA), and di-[4-(N,N-ditolyl-amino)phenyl]cyclohexane (TAPC). Additionally, polymeric and copolymeric hole transport materials can be used. Polymeric hole transport materials include poly(N-vinylcarbazole) (PVK), polythiophene, polypyrrole, and polyaniline. Copolymers include PEDOT:PSS. In some embodiments, the hole transport layer has a thickness of about 10 nm to 70 nm, for example, 40 nm.
[0135] In some embodiments, the electron transport layer (or electron transport layer or electron transport layer or electron transporting layer) comprises an organic compound. The organic compounds may include, but are not limited to, 1,3,5-tris(phenyl-2-benzimidazolyl)-benzene (TPBI), 1,3,5-tri[(3-pyridyl)-phenyl-3-yl]benzene (TmPyPB), bathocuproine (BCP), bathophenanthroline (BPhen) and bis(2-methyl-8-quinolinolato)-4-(phenylphenolate)-aluminum (BAlq), 1,3,5-tri[(3-pyridyl)-phenyl-3-yl]benzene (TmPyPB), 1,3-bis[3,5-di(pyridin-3-yl)-phenyl]benzene (BmPyPhB) and 1,3,5-tris(6-(3-(pyridin-3-yl)phenyl)pyridin-2-yl)benzene (Tm3PyP26PyB). In some embodiments, the electron transport layer has a thickness of about 10 nm to 60 nm, for example, 40 nm.
[0136] In some embodiments, the light-emitting device may include a carrier confinement layer (or carrier confinement layer). The carrier confinement layer is a layer inserted between the hole transport layer and the light-emitting layer, or between the light-emitting layer and the electron transport layer. Preferably, the carrier confinement layer improves the performance of the light-emitting device. In some embodiments, the carrier confinement layer includes an organic compound. Examples of the organic compound include, but are not limited to, CBP, TCTA, 3TPYMB, BmPyPhB, and Tm3PyP26PyB. In some embodiments, the carrier confinement layer has a thickness of about 5 nm to about 50 nm, for example, about 10 nm to about 50 nm.
[0137] Preferably, the anode of the light-emitting device comprises indium tin oxide coated glass. Preferably, the cathode of the light-emitting device comprises lithium fluoride, aluminum, or a combination thereof. In some embodiments, the lithium fluoride forms a layer having a thickness of about 0.05 nm to about 5 nm, for example, about 1 nm. In some embodiments, the aluminum forms a layer having a thickness of about 50 nm to about 250 nm, about 50 nm to about 200 nm, for example, about 150 nm.
[0138] OLEDs comprising emitter platinum(II) binuclear complexes can demonstrate a maximum current efficiency (CE) of up to 35 cd / A. In some embodiments, the CE can include, but is not limited to, values of about 5 cd / A, 7.5 cd / A, 10 cd / A, 15 cd / A, 20 cd / A, 25 cd / A, 30 cd / A, or 35 cd / A. 1000 cd / m 2 The CE value at a luminance (or luminance) of 1000 cd / m may be up to 30 cd / A. 2The CE at a luminance (or luminance) of about 2 cd / A, 2.5 cd / A, 5 cd / A, 10 cd / A, 15 cd / A, 20 cd / A, 25 cd / A or 30 cd / A may be mentioned, but is not limited to these values.
[0139] OLEDs comprising emitter platinum(II) dinuclear complexes can demonstrate a maximum power efficiency (PE) of up to 30 lumens per watt (lm / W). In some embodiments, the PE can include, but is not limited to, values of about 5 lm / W, 10 lm / W, 15 lm / W, 20 lm / W, 25 lm / W, or 30 lm / W. 1000 cd / m 2 The value of PE at a luminance (or luminance) of 1000 cd / m may be up to 25 lm / W. In some embodiments, 2 Examples of PE at a luminance (or luminance) of about 5 lm / W, 5.5 lm / W, 6 lm / W, 6.5 lm / W, 10 lm / W, 15 lm / W, 20 lm / W, and 25 lm / W can be mentioned, but are not limited to these values.
[0140] OLEDs comprising emitter platinum(II) dinuclear complexes can demonstrate a maximum external quantum efficiency (EQE) of up to about 30%. In some embodiments, the EQE can include, but is not limited to, values of about 10-30%. 1000 cd / m 2 The EQE value at a luminance (or luminance) of 1000 cd / m may be up to 20% or 25%. 2 Examples of PE at this brightness (or luminance) include, but are not limited to, values of about 1% to about 20%, about 1% to about 15%, about 1% to about 10%, or about 1% to about 5%.
[0141] The compositions and methods of the present disclosure can be further understood by the following numbered sections (or paragraphs).
[0142] 1. A compound having the structure of formula Ia: [ka] Formula Ia
[0143] During the ceremony The compound has an overall neutral, negative or positive charge.
[0144] A dashed straight line indicates the presence or absence of a bond.
[0145] A and A' are independently selected from substituted cycloalkyl, unsubstituted cycloalkyl, substituted cycloalkenyl, unsubstituted cycloalkenyl, substituted cycloalkynyl, unsubstituted cycloalkynyl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 and C1-C2-C3-C4-C6-C8-C9-, or a fused combination thereof; preferably, A and A' are independently substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyaryl, unsubstituted polyaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C1-C2-C3-C4-C8-C9 ... 20 Heterocyclyl, unsubstituted C1-C 20 heterocyclyl, or a fused combination thereof (or a fused combination thereof).
[0146] X5 and X5’ are independently carbon or nitrogen and are independently bonded to one or no hydrogen atoms depending on the valence (or bond valency); preferably, X and X 5’ is carbon.
[0147] R5, R6, R 5’ and R 6’ are independently absent, hydrogen, substituted alkyl, unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, substituted aryl, unsubstituted aryl, halogen, hydroxyl, thiol, cyano, nitro-, unsubstituted alkoxy, substituted alkoxy, unsubstituted aroxy, substituted aroxy, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, unsubstituted alkylthio, substituted alkylthio, unsubstituted carbonyl, substituted carbonyl, unsubstituted carboxyl, substituted carboxyl, unsubstituted ester, substituted ester, substituted C-C 20 Cycloalkyl, unsubstituted C3-C 20 Cycloalkyl, Substituted C1-C 20 Heterocyclyl, unsubstituted C1-C 20 Heterocyclyl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 Cycloalkenyl, substituted C3-C 20 Cycloalkynyl, unsubstituted C3-C 20 cycloalkynyl; or R5, R6, R 5’ and R 6’ together with the atom to which they are attached, represent substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20heterocyclyl, a fused combination thereof (or a fused combination thereof), or preferably R, R, R 5’ and R 6’ is independently absent, hydrogen, substituted alkyl, unsubstituted alkyl, substituted aryl, or unsubstituted aryl.
[0148] A1, A2, A3, A4, A 1’ , A 2’ , A 3’ and A 4’ is independently absent, hydrogen, deuterium, carbon, nitrogen, unsubstituted aryl, or unsubstituted aryl, and if present, is independently bonded to 1, 2, 3, 4, 5, or no hydrogen atoms, depending on the valence (or bond valency).
[0149] R 1a , R 2a , R 3a , R 4a , R 1a’ , R 2a’ , R 3a’ and R 4a’ is independently absent, hydrogen, deuterium, substituted alkyl, unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, substituted aryl, unsubstituted aryl, halogen, hydroxyl, thiol, cyano, nitro-, unsubstituted alkoxy, substituted alkoxy, unsubstituted aroxy, substituted aroxy, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, unsubstituted alkylthio, substituted alkylthio, unsubstituted carbonyl, substituted carbonyl, unsubstituted carboxyl, substituted carboxyl, unsubstituted ester, substituted ester, substituted C-C 20 Cycloalkyl, unsubstituted C3-C 20 Cycloalkyl, Substituted C1-C20 Heterocyclyl, unsubstituted C1-C 20 Heterocyclyl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 Cycloalkenyl, substituted C3-C 20 Cycloalkynyl, unsubstituted C3-C 20 Cycloalkynyl, unsubstituted C1-C 20 heterocyclyl, a fused combination thereof (or a fused combination thereof) (e.g., dibenzofuran-4-yl, dibenzofuran-3-yl, dibenzothiopen-4-yl, dibenzothiopen-3-yl, etc.), or R 1a and R 2a , R 2a and R 3a , R 3a and R 4a , R 1a’ and R 2a’ , R 2a’ and R 3a’ , R 3a’ and R 4a’ or combinations thereof, together with the atom to which they are attached, are substituted cycloalkyl, unsubstituted cycloalkyl, substituted cycloalkenyl, unsubstituted cycloalkenyl, substituted cycloalkynyl, unsubstituted cycloalkynyl, substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyaryl, unsubstituted polyaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 heterocyclyl, a fused combination thereof (or a fused combination thereof), or R 1a and R 2a , R 2a and R 3a , R 3a and R 4a , R 1a’ and R 2a’ , R 2a’ and R 3a’, R 3a’ and R 4a’ or any combination thereof, taken together with the atom to which they are attached, is substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyaryl, unsubstituted polyaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 heterocyclyl, which form fused combinations (or combinations thereof which are fused);
[0150] L1 and L 1’ are independently substituted alkyl, unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, unsubstituted alkoxy, substituted alkoxy, unsubstituted aroxy, substituted aroxy, unsubstituted alkylthio, substituted alkylthio, unsubstituted carbonyl, substituted carbonyl, unsubstituted carboxyl, substituted carboxyl, unsubstituted ester, substituted ester, unsubstituted ether, substituted ether, unsubstituted polyether, substituted polyether, substituted amino, unsubstituted amino, substituted amido, unsubstituted amido, substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyaryl, unsubstituted polyaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C3-C 20 Cycloalkyl, unsubstituted C3-C 20 Cycloalkyl, Substituted C1-C 20 Heterocyclyl, unsubstituted C1-C 20 Heterocyclyl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 Cycloalkenyl, substituted C3-C20 Cycloalkynyl, unsubstituted C3-C 20 cycloalkynyl, or a fused combination thereof (or a fused combination thereof).
[0151] 2. L1 and L 1’ is independently substituted or unsubstituted alkyl.
[0152] 3. L1 and L 1’ are independently substituted C1-C 10 Alkyl, unsubstituted C1-C 10 Alkyl, Substituted C2-C 10 Alkyl or unsubstituted C2-C 10 Alkyl, preferably the substituted alkyl, the substituted C-C 10 Alkyl, the substituted C-C 10 An alkyl group can have one or more alkyl substituents (e.g., methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl), one or more ether linkages, one or more amine groups (e.g., substituted or unsubstituted amines), one or more substituted aryl groups, one or more substituted heteroaryl groups, one or more substituted C-C 20 Cycloalkyl groups, one or more substituted C1-C 20 A compound according to claim 1 or 2, which comprises a heterocyclyl group, or a combination thereof.
[0153] 4. R 1a , R 2a , R 3a , R 4a , R 1a’ , R 2a’ , R 3a’ and R 4a’ is independently absent, hydrogen, deuterium, substituted alkyl, unsubstituted alkyl, substituted aryl or unsubstituted aryl; or R 1aand R 2a , R 2a and R 3a , R 3a and R 4a , R 1a’ and R 2a’ , R 2a’ and R 3a’ , R 3a’ and R 4a’ or any combination thereof, taken together with the atom to which they are attached, is substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyaryl, unsubstituted polyaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 A compound according to any one of items 1 to 3, which is a heterocyclyl or a fused combination thereof (or a fused combination thereof).
[0154] 5. The compound according to any one of items 1 to 4, having the structure of formula IIa or IIb: [ka] Formula IIa or [ka] Formula IIb
[0155] During the ceremony A dashed straight line indicates the presence or absence of a bond.
[0156] X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X 4’ is independently carbon, nitrogen, oxygen, or sulfur, if present, and is independently bonded to one hydrogen atom or to no hydrogen atoms, depending on the valence (or valency).
[0157] R1, R2, R3, R4, R 1’ , R 2’ , R 3’ and R 4’ is independently absent, hydrogen, deuterium, substituted alkyl (e.g., trifluoromethyl), unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, substituted aryl (e.g., mesityl (2,4,6-trimethylphenyl), 3,5-di-tert-butylphenyl, 2,6-dimethylphenyl), unsubstituted aryl, halogen (e.g., fluorine), hydroxyl, thiol, cyano, nitro-, unsubstituted alkoxy, substituted alkoxy, unsubstituted aroxy, substituted aroxy, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, unsubstituted alkylthio, substituted alkylthio, unsubstituted carbonyl, substituted carbonyl, unsubstituted carboxyl, substituted carboxyl, unsubstituted ester, substituted ester, substituted C-C 20 Cycloalkyl, unsubstituted C3-C 20 Cycloalkyl, Substituted C1-C 20 Heterocyclyl, unsubstituted C1-C 20 Heterocyclyl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 Cycloalkenyl, substituted C3-C 20 Cycloalkynyl or unsubstituted C3-C 20 cycloalkynyl; or R1 and R2, R2 and R3, R3 and R4, R 1’ and R 2’ , R 2’ and R 3’ , R 3’ and R 4’or combinations thereof, together with the atom to which they are attached, are substituted cycloalkyl, unsubstituted cycloalkyl, substituted cycloalkenyl, unsubstituted cycloalkenyl, substituted cycloalkynyl, unsubstituted cycloalkynyl, substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyaryl, unsubstituted polyaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 heterocyclyl, or a fused combination thereof (or a fused combination thereof).
[0158] 6. R1, R2, R3, R4, R 1’ , R 2’ , R 3’ and R 4’ are independently absent, hydrogen, deuterium, substituted alkyl (e.g., trifluoromethyl), unsubstituted alkyl, substituted aryl (e.g., mesityl (2,4,6-trimethylphenyl), 3,5-di-tert-butylphenyl, 2,6-dimethylphenyl), unsubstituted aryl, halogen (e.g., fluorine), or R1 and R2, R2 and R3, R3 and R4, R 1’ and R 2’ , R 2’ and R 3’ , R 3’ and R 4’ or any combination thereof, together with the atom to which they are attached, represents substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 A compound according to claim 5, which forms a fused combination (or a fused combination) of heterocyclyl.
[0159] 7. The compound according to any one of items 1 to 6, having the structure of formula IIIa or IIIb: [ka] Formula IIIa or [ka] Formula IIIb
[0160] During the ceremony A dashed straight line indicates that a bond is either present or absent.
[0161] A5, A6, A 5’ and A 6’ are independently hydrogen, deuterium, unsubstituted alkyl, substituted alkyl, substituted aryl, unsubstituted aryl, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, substituted C-C 20 Heterocyclyl or unsubstituted C1-C 20 It is heterocyclyl, or preferably hydrogen, unsubstituted alkyl, substituted alkyl, deuterium, substituted aryl, or unsubstituted aryl.
[0162] 8. A5, A6, A 5’ and A 6’ is hydrogen or deuterium.
[0163] 9. A5, A6, A 5’ and A 6’ teeth, (i) unsubstituted alkyl (e.g., unsubstituted C-C 10 alkyl, unsubstituted C1-C5 alkyl, or unsubstituted C1-C3 alkyl) or substituted alkyl (e.g., substituted C1-C 10alkyl, substituted C1-C5 alkyl, or substituted C1-C3 alkyl), or (ii) hydrogen, substituted aryl, or unsubstituted aryl (However, at least one of A5 and A6, or A 5’ and A 6’ wherein at least one of is substituted or unsubstituted aryl.
[0164] 10. In formula IIa or formula IIIa, X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X 4’ is carbon and is independently bonded to one hydrogen atom or to no hydrogen atoms depending on the valence (or bond valence).
[0165] 11. In formula IIa or formula IIIa, one or more of X1, X2, X3 and X4, and one or more of X 1’ , X 2’ , X 3’ and X 4’ is nitrogen, and X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X 4’ are independently bonded to one hydrogen atom or not bonded to a hydrogen atom, depending on the valence (or bond valence).
[0166] 12. In formula IIa or formula IIIa, X2 and X 2’ is nitrogen, and X1, X3, X4, X 1’ , X 3’ and X 4’ is carbon, and X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X 4’are independently bonded to one hydrogen atom or not bonded to a hydrogen atom, depending on the valence (or bond valence).
[0167] 13. In formula IIa or formula IIIa, R1, R2, R3, R4, R 1’ , R 2’ , R 3’ and R 4’ are independently absent, hydrogen, deuterium, substituted alkyl (e.g., trifluoromethyl), unsubstituted alkyl, substituted aryl (e.g., mesityl (2,4,6-trimethylphenyl), 3,5-di-tert-butylphenyl, 2,6-dimethylphenyl), unsubstituted aryl, halogen (e.g., fluorine), or R1 and R2, R2 and R3, R3 and R4, R 1’ and R 2’ , R 2’ and R 3’ , R 3’ and R 4’ or any combination thereof, together with the atom to which they are attached, represents substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 A compound according to any one of items 5 to 12, which is a heterocyclyl or a fused combination thereof (or a fused combination thereof).
[0168] 14. In formula IIa or formula IIIa, R1, R2, R3, R4, R 1’ , R 2’ , R 3’ and R 4’is independently absent, hydrogen, deuterium, substituted alkyl (e.g., trifluoromethyl), unsubstituted alkyl, substituted aryl (e.g., mesityl (2,4,6-trimethylphenyl), 3,5-di-tert-butylphenyl, 2,6-dimethylphenyl), unsubstituted aryl, or halogen (e.g., fluorine).
[0169] 15. In formula IIa or formula IIIa, R1 and R2, R2 and R3, R3 and R4, R 1’ and R 2’ , R 2’ and R 3’ , R 3’ and R 4’ or any combination thereof, together with the atom to which they are attached, represents substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 A compound according to any one of items 5 to 13, which is a heterocyclyl or a fused combination thereof (or a fused combination thereof).
[0170] 16. In formula IIa or formula IIIa, R1 and R2, R2 and R3, R3 and R4, R 1’ and R 2’ , R 2’ and R 3’ , R 3’ and R 4’ , or combinations thereof, together with the atoms to which they are attached, [ka] or [ka] The compound according to any one of items 5 to 13 or 15, which forms
[0171] During the ceremony Q5 is NR 14 , carbon, or sulfur, or oxygen; R 10 ~R 14 are independently absent, hydrogen, substituted alkyl, unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, substituted aryl, unsubstituted aryl, halogen, hydroxyl, amino, amido, ether, thiol, cyano, nitro, unsubstituted alkoxy, substituted alkoxy, unsubstituted aroxy, substituted aroxy, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, unsubstituted carbonyl, substituted carbonyl, unsubstituted ester, substituted ester, substituted C-C 20 Heterocyclyl or unsubstituted C1-C 20 It is a heterocyclyl.
[0172] 17. Q5 is NR 14 , carbon, or sulfur, or oxygen, e.g., oxygen; R 10 ~R 14 17. The compound according to paragraph 16, wherein:
[0173] 18. Q5 is oxygen; R 10 ~R 14 18. The compound according to claim 16 or 17, wherein:
[0174] 19. In formula IIb or formula IIIb, one or more of X1, X2 and X3, and one or more of X 1’ , X 2’ and X 3’ is sulfur, oxygen or nitrogen, and X1, X2, X3, X 1’ , X 2’ and X3’ are independently bonded to one hydrogen atom or not bonded to a hydrogen atom, depending on the valence (or bond valence).
[0175] 20. In formula IIb or formula IIIb, one of X1, X2 and X3, and X 1’ , X 2’ and X 3’ One of them is sulfur, and the other is X1, X2, X3, and X 1’ , X 2’ and X 3’ are independently bonded to one hydrogen atom or not bonded to a hydrogen atom, depending on the valence (or bond valence).
[0176] twenty one. In formula IIb or formula IIIb, one of X1, X2 and X3, and X 1’ , X 2’ and X 3’ One of the is oxygen, and X1, X2, X3, X 1’ , X 2’ and X 3’ are independently bonded to one hydrogen atom or not bonded to a hydrogen atom, depending on the valence (or bond valence).
[0177] twenty two. In formula IIb or formula IIIb, R1, R2, R3, R 1’ , R 2’ and R 3’ are independently absent, hydrogen, substituted alkyl, unsubstituted alkyl, substituted aryl, unsubstituted aryl, halogen, or R1 and R2, R2 and R3, R 1’ and R 2’ , R 2’ and R 3’or any combination thereof, together with the atom to which they are attached, represents substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 A compound according to any one of items 5 to 9 or any one of items 19 to 21, which is a heterocyclyl or a fused combination thereof (or a fused combination thereof).
[0178] twenty three. In formula IIb or formula IIIb, R1, R2, R3, R 1’ , R 2’ and R 3’ The compound according to any one of items 5 to 9 or any one of items 19 to 22, wherein is absent, hydrogen, or a combination thereof.
[0179] twenty four. In formula IIb or formula IIIb, R1 and R2, R2 and R3, R 1’ and R 2’ , R 2’ and R 3’ or any combination thereof, together with the atom to which they are attached, represents substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C-C 20 Heterocyclyl, unsubstituted C1-C 20 A compound according to any one of items 5 to 9 or any one of items 19 to 22, which is a heterocyclyl or a fused combination thereof (or a fused combination thereof).
[0180] twenty five. In formula IIb or formula IIIb, R1 and R2, R2 and R3, R 1’ and R 2’ , R 2’ and R 3’ , or combinations thereof, together with the atoms to which they are attached, [ka] or [ka] The compound according to any one of items 5 to 9, any one of items 19 to 22, or 23, which forms
[0181] During the ceremony Q5 is NR 14 , carbon, or sulfur, or oxygen; R 10 ~R 14 are independently absent, hydrogen, substituted alkyl, unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, substituted aryl, unsubstituted aryl, halogen, hydroxyl, amino, amido, ether, thiol, cyano, nitro, unsubstituted alkoxy, substituted alkoxy, unsubstituted aroxy, substituted aroxy, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, unsubstituted carbonyl, substituted carbonyl, unsubstituted ester, substituted ester, substituted C-C 20 Heterocyclyl or unsubstituted C1-C 20 It is a heterocyclyl.
[0182] 26. Q5 is NR 14 , carbon, sulfur or oxygen, e.g., sulfur; R 10 ~R 14 28. The compound of claim 27, wherein:
[0183] 27. Q5 is sulfur; R 10 ~R 1427. The compound according to claim 25 or 26, wherein is hydrogen.
[0184] 28. The compound according to any one of items 1 to 6, wherein in formula Ia, IIa or IIb, the compound has a structure of formula IVa or IVb: [ka] Formula IVa or [ka] Formula IVb
[0185] During the ceremony A1, A2, A3, A4, A 1’ , A 2’ , A 3’ and A 4’ is independently carbon, nitrogen, oxygen, or sulfur and is independently bonded to one hydrogen atom or to no hydrogen atoms, depending on the valence (or valency).
[0186] X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X 4’ is independently carbon, nitrogen, oxygen, or sulfur, if present, and is independently bonded to one hydrogen atom or to no hydrogen atoms, depending on the valence (or valency).
[0187] 29. In formula IVa, A1, A2, A3, A4, A 1’ , A 2’ , A 3’ and A 4’ are carbons, which are independently bonded to one or no hydrogen atoms, depending on the valence (or bond valence), and X1, X2, X3, X4, X5, X6, X7, X8, X9, X10, X11, X12, X13, X14, X15, X16, X17, X18, X19, X20, X21, X22, X23, X24, X25, X30, X31, X32, X33, X34, X35, X36, X37, X38, X40, X41, X42, X43, X44, X45, X46, X47, X48, X49, X50, X51, X52, X53, X54, X55, X56, X66, X77, X78, X89, X90, X91, X92, X93, X94, X95, X96, X107, X118, X119, X129, X130, X140, X151, X161, X172, X183, X194, X195, X196, X197, X198, X199, X201, X202, X203, X204, X210, X221, X230, X241, X252, X330, X341, X353, X46, X54, X66, X77, X89, X91, X102, X113, X124, X135, X253, X365, X47, X55, X67, X78, X89, X91, X103, X114, X125, X135, X268 1’ , X 2’ , X 3’ and X 4’is a carbon and is independently bonded to one hydrogen atom or to no hydrogen atoms, depending on the valence (or bond valence).
[0188] 30. In formula IVa, R1, R2, R3, R4, R 1’ , R 2’ , R 3’ and R 4’ 30. The compound of claim 28 or 29, wherein: is independently absent, hydrogen, deuterium, substituted alkyl, unsubstituted alkyl, substituted aryl, unsubstituted aryl, or halogen.
[0189] 31. In formula IVa, R 1a , R 2a , R 3a , R 4a , R 1a’ , R 2a’ , R 3a’ and R 4a’ is independently absent, hydrogen, deuterium, substituted alkyl, unsubstituted alkyl, substituted aryl, or unsubstituted aryl; or R 1a and R 2a , R 2a and R 3a , R 3a and R 4a , R 1a’ and R 2a’ , R 2a’ and R 3a’ , R 3a’ and R 4a’ or combinations thereof, together with the atoms to which they are attached, form a substituted or unsubstituted aryl.
[0190] 32. In formula IVa, R 1a and R 2a , R 3a and R 4a , R 1a’ and R 2a’ , R3a’ and R 4a’ The compound according to any one of items 28 to 31, wherein: together with the atom to which they are attached, form a substituted or unsubstituted aryl.
[0191] 33. In formula Ia, formula IIa or formula IVa, one or more of A1, A2, A3 and A4 are nitrogen and one or more of A 1’ , A 2’ , A 3’ and A 4’ is nitrogen, A1, A2, A3, A4, A 1’ , A 2’ , A 3’ and A 4’ are independently bonded to one hydrogen atom or not bonded to a hydrogen atom, depending on the valence (or bond valence), and X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X 4’ is carbon and is independently bonded to one hydrogen atom or to no hydrogen atoms, depending on the valence (or bond valence).
[0192] 34. For Formula IVa, R1, R2, R3, R4, R 1’ , R 2’ , R 3’ and R 4’ is independently absent, hydrogen, deuterium, substituted alkyl, unsubstituted alkyl, substituted aryl (e.g., mesityl (2,4,6-trimethylphenyl), 3,5-di-tert-butylphenyl, 2,6-dimethylphenyl), unsubstituted aryl, or halogen (e.g., fluorine).
[0193] 35. R 1a , R 2a , R 3a , R 4a , R 1a’ , R 2a’, R 3a’ and R 4a’ is independently absent, hydrogen, deuterium, substituted alkyl, unsubstituted alkyl, substituted aryl, or unsubstituted aryl (e.g., phenyl).
[0194] 36. In formula IVa, one of A1, A2, A3 and A4 is nitrogen and the other three are carbon; A 1’ , A 2’ , A 3’ and A 4’ One of them is nitrogen and the other three are carbon, A1, A2, A3, A4, A 1’ , A 2’ , A 3’ and A 4’ are independently bonded to one hydrogen atom or not bonded to a hydrogen atom, depending on the valence (or bond valence).
[0195] 37. In formula IVa, two of A1, A2, A3 and A4 are nitrogen and the other two are carbon; A 1’ , A 2’ , A 3’ and A 4’ Two of them are nitrogen and the other two are carbon. A1, A2, A3, A4, A 1’ , A 2’ , A 3’ and A 4’ are independently bonded to one hydrogen atom or not bonded to a hydrogen atom, depending on the valence (or bond valence).
[0196] 38. In formula Ia, formula IIa or formula IVa, one or more of A1, A2, A3 and A4 are oxygen, nitrogen or sulfur, and one or more of A 1’ , A 2’ , A 3’ and A 4’is oxygen, nitrogen or sulfur, and A1, A2, A3, A4, A 1’ , A 2’ , A 3’ and A 4’ are independently bonded to one hydrogen atom or not bonded to a hydrogen atom, depending on the valence (or bond valence), and are one or more of X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X 4’ is oxygen, nitrogen or sulfur, and X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X 4’ are independently bonded to one hydrogen atom or not bonded to a hydrogen atom, depending on the valence (or bond valence).
[0197] 39. In formula IVa, R1, R2, R3, R4, R 1’ , R 2’ , R 3’ and R 4’ is independently absent, hydrogen, deuterium, substituted alkyl, unsubstituted alkyl, substituted aryl, unsubstituted aryl, or halogen (e.g., fluorine).
[0198] 40. R 1a , R 2a , R 3a , R 4a , R 1a’ , R 2a’ , R 3a’ and R 4a’ 40. The compound of claim 38 or 39, wherein:
[0199] 41. In formula IVa, one or more of A1, A2, A3 and A4 are nitrogen and one or more of A 1’, A 2’ , A 3’ and A 4’ is nitrogen, A1, A2, A3, A4, A 1’ , A 2’ , A 3’ and A 4’ are independently bonded to one hydrogen atom or not bonded to a hydrogen atom, depending on the valence (or bond valence), and are one or more of X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X 4’ is nitrogen, and X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X 4’ are independently bonded to one hydrogen atom or not bonded to a hydrogen atom, depending on the valence (or bond valence).
[0200] 42. In formula IVa, one of A1, A2, A3 and A4 is nitrogen and the other three are carbon; A 1’ , A 2’ , A 3’ and A 4’ One of them is nitrogen and the other three are carbon, A1, A2, A3, A4, A 1’ , A 2’ , A 3’ and A 4’ are independently bonded to one hydrogen atom or not bonded to a hydrogen atom depending on the valence (or bond valence); one of X1, X2, X3 and X4 is nitrogen and the other three are carbon; and X 1’ , X 2’ , X 3’ and X 4’ One of the atoms is nitrogen and the other three are carbon, X1, X2, X3, X4, X 1’ , X 2’ , X 3’ and X 4’ are independently bonded to one hydrogen atom or not bonded to a hydrogen atom, depending on the valence (or bond valence).
[0201] 43. Item 42. The compound according to any one of items 1 to 42, having the following structure: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0202] 44. 44. An organic electronic device comprising the compound according to any one of items 1 to 43.
[0203] 45. 45. The organic electronic component according to claim 44, wherein the organic electronic component is an organic light-emitting diode (or organic light-emitting diode) (OLED) or an electrochemiluminescent cell (or light-emitting electrochemical cell) (LEEC).
[0204] 46. 46. The organic electronic component according to claim 44 or 45, wherein the compound is contained in an emitting layer.
[0205] 47. An anode; A cathode; a hole transport region (or hole transport region or hole transport region or hole transport region); Electron transport region (or electron transport region) and The hole transport region includes a hole injection layer (or hole injection layer or hole injection layer) and / or a hole transport layer (or hole transport layer or hole transport layer), and further includes an electron blocking layer (or electron blocking layer) as required; the electron transport region includes an electron transport layer (or electron transport layer) and / or an electron injection layer (or electron injection layer), and optionally includes a hole blocking layer (or hole blocking layer or hole blocking layer); the light-emitting layer is disposed between the anode and the cathode; the hole transport region is disposed between the anode and the light-emitting layer; the electron transport region is disposed between the cathode and the light-emitting layer; 47. The organic electronic component according to any one of items 44 to 46.
[0206] 48. Item 48. The organic electronic component according to item 46 or 47, wherein the light-emitting layer is formed (or produced or made) by vacuum deposition (or reduced pressure deposition or vacuum deposition), spin coating (or spin coat) or ink printing (or ink printing or ink printing) (e.g. ink jet printing (or ink jet printing or ink jet printing) or roll-to-roll printing (or roll-to-roll printing or roll-to-roll printing)).
[0207] 49. 44. A light-emitting layer comprising the compound according to any one of items 1 to 43.
[0208] 50. The compound further comprises a pure organic emitter (or a pure organic emitter), the compound comprising: (i) acting as a sensitizer to transfer energy to the pure organic emitter; (ii) having a higher singlet state than the pure organic emitter; 50. The light-emitting layer of paragraph 49.
[0209] 51. 51. An OLED comprising an emissive layer according to paragraph 49 or 50.
[0210] 52. The devices may be stationary visual display units, mobile visual display units, illumination units, keyboards, clothes, ornaments, garment accessories, wearable devices, medical monitoring devices, wall papers, tablet computers, laptops, advertisement panels, panel display units, household appliances or office appliances. 52. A device comprising the OLED of claim 51, selected from the group consisting of OLEDs, OLEDs having a wavelength of 100 nm to 150 nm ... and OLEDs having a wavelength of 100 nm to 150 nm. EXAMPLES
[0211] (Example) Example 1: Synthesis and characterization of compounds The new platinum(II) binuclear complex (e.g., fluorine-free complex) exhibits strong deep blue phosphorescence. The excellent emission quantum yield is up to 0.74 (thin film, room temperature). The emission can be further tuned by the substituent(s) on the cyclometalating NHC ligand. The most notable features of this new Pt(II) emitter are its deep blue emission (emission maximum at 447 nm) and very short radiative lifetime. The emission wavelength is 100 nm (up to about 100 nm lifetime) (up to about 2 μs). Preliminary results of the evaporated deep blue OLED show an EQE of 12.1% and a CE of 7.53 cd / A, with a CIE(x,y) of 0.16,0.07. To the applicant's best knowledge, this is one of the few examples of a metal complex based device that is able to meet the National Television System Committee (NTSC) definition of the pure blue color coordinates of (0.14,0.08).
[0212] material and method Chemicals used in the synthesis were purchased from commercial sources (e.g., Dieckmann, Tiv Scientific, J & K Scientific, BLDpharm, Bidepharm, Strem Chemicals). These chemicals were used directly without further treatment. Solvents used in the synthesis were purchased from Duksan, RCI Labscan, Scharlau. These solvents were used directly without further treatment.
[0213] Characterization 1 H and 13 C NMR spectra were recorded on a DPX-400 or DPX-500 Bruker FT-NMR spectrometer. The chemical shifts of the proton (H) or carbon (C) signals were calibrated (by the corresponding residual solvent signals). High resolution mass spectra were measured on a Bruker Impact II mass spectrometer.
[0214] OLED manufacturing process (or manufacturing method or manufacturing process) Indium-Tin-Oxide (ITO) coated glass (sheet resistance 10 Ω / sq) was used as the anode substrate. Prior to film deposition, the patterned ITO substrate was cleaned with detergent, rinsed with deionized water, acetone, and isopropanol, and then dried in an oven (clean room, 1 h). The slide was then treated in a UV-ozone chamber for 5 min. The Kurt J. Lesker SPECTROS reduced pressure deposition system (10 -7 The OLEDs were fabricated at a base pressure of 0.5 Ås in a vacuum chamber. -1 The doping process in the light-emitting layer (or emissive layer) (EML) was realized using co-deposition technology. Then, LiF (1.2 nm) and Al (100 nm) were thermally evaporated at a rate of 0.02 nm s, respectively. -1 and 0.2 nm s -1 The film thickness was determined in situ (using a calibrated vibrating quartz crystal sensor).
[0215] OLED characterization Current density-brightness-voltage characteristics, EL spectra, and EQE were obtained for the electroluminescent (EL) devices using a Keithley 2400 source-meter and an absolute external quantum efficiency measurement system (C9920-12, Hamamatsu Photonics). All devices were encapsulated with a 200 nm thick thin film of Al2O3 deposited by atomic layer deposition (ALD) in a Kurt J. Lesker SPECTROS ALD system and then measured.
[0216] (i) Synthesis of Ligand Scheme 1 shows the synthesis of tridentate (or tridentate) NHC ligands (L1 and L2). [ka]
[0217] Synthesis of 9-bromononane-2,4-dione (Chen et al., Chem. Commun., 2011, 47, 9519-9521) Acetylacetone (1 eq.) was added to NaH (1.15 eq.) in 20 mL of dry THF at 0° C. The reaction mixture was stirred for 30 min. Then, n-BuLi (1.2 eq.) was added. The reaction mixture was stirred for 30 min more. Dibromoalkane (1.5 eq., n1=4 (L1 / L2)) was added and stirred for 2 h at 0° C. and 2 h at room temperature. Water was added and the reaction mixture was acidified to a pH of about 2. The aqueous phase was extracted with CHCl3. The combined organic fractions were dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was used in the next step without further purification. [ka]
[0218] 1-Phenylimidazole (for L1) or 3-phenyl-3H-imidazo[4,5-b]pyridine (Pinter et al., Organometallics 2016, 35, 673-680) (for L2) (0.66 equiv.) and 9-bromononane-2,4-dione (Chen et al., Chem. Commun., 2011, 47, 9519-9521) (1.00 equiv.)) were stirred in acetone (1 mL per 1 mmol of imidazole) at 100 °C for 48 h. The solvent was removed under reduced pressure and the residue was used in the next step without further purification. Hydrazine hydrate (1.1 equiv.) and EtOH (2 mL per 1 mmol of imidazole) were added and the reaction mixture was refluxed overnight. The solvent was removed under reduced pressure and the residue was purified using a silica gel column (acetone / EtOH).
[0219] L1 Overall Yield: 54% 1H NMR (500 MHz, DMSO): δ 11.99 (s, 1H), 9.80 (s, 1H), 8.30 (s, 1H), 8.01 (s, 1H), 7.76 (d, J = 8.1 Hz, 2H), 7.64 (t, J = 7.7 Hz, 2H), 7.56 (t, J = 7.4 Hz, 1H), 5.73 (s, 1H), 4.21 (t, J = 7.2 Hz, 2H), 3.41 (q, J = 6.8 Hz, 2H), 2.08 (s, 3H), 1.93 - 1.84 (m, 2H), 1.62 - 1.53 (m, 2H), 1.33 - 1.27 (m, 2H). HRMS(ESI)(C 18 H 23 N4[M] + : Calculated value 295.1923, measured value 295.1916 L2 Total yield: 22% 1 H NMR (500 MHz, DMSO): δ 10.44 (s, 1H), 8.82 (d, J = 4.8 Hz, 1H), 8.75 (d, J = 8.4 Hz, 1H), 7.93 (d, J = 7.9 Hz, 2H), 7.90 - 7.85 (m, 1H), 7.75 (t, J = 7.7 Hz, 2H), 7.68 (t, J = 7.6 Hz, 1H), 5.94 (s, 1H), 4.58 (t, J = 7.1 Hz, 2H), 2.19 (s, 3H), 2.06 - 2.00 (m, 2H), 1.70 - 1.62 (m, 2H), 1.56 - 1.53 (m, 2H), 1.50 - 1.42 (m, 2H).
[0220] (ii)Platinum(II)エミッタの synthesis Syntheses of スキーム2は and エミッタPlatinum(II) dinuclear complex are shown.
change
change
[0221] L1 or L2 (1 equiv.), Pt(COD)Cl2 (1.04 equiv.) and NaOAc (3 equiv.) were stirred in 1,4-dioxane (1 mL per 0.1 mmol of imidazolium salt) at 160° C. for 3 days. Water was added to the reaction mixture and the aqueous phase was extracted with DCM. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified using a silica gel column (using DCM / hexane as eluent).
[0222] Pt-1 Yield: 17% 1 H NMR (500 MHz, DMSO): δ 7.89 (s, 2H), 7.26 (s, 2H), 7.21 (d, J = 7.6 Hz, 2H), 6.96 - 6.87 (m, 4H), 6.74 (t, J = 7.3 Hz, 2H), 6.00 (s, 2H), 3.65 - 3.57 (m, 2H), 3.47 - 3.40 (m, 2H), 2.97 - 2.90 (m, 2H), 2.63 - 2.58 (m, 2H), 2.16 (s, 6H), 2.02 - 1.92 (m, 2H), 1.86 - 1.74 (m, 2H), 1.74 - 1.59 (m, 4H), 1.57 - 1.48 (m, 2H), 1.30 - 1.24 (m, 2H). HRMS(ESI)(C 36 H 41 N8Pt2[M+H] + ): Calculated value 975.2750, measured value 975.2724
[0223] Pt-2 Yield: 2% 1H NMR (500 MHz, CD2Cl2): δ 8.36 (s, 1H), 8.35 (s, 1H), 7.61 (d, J = 8.1 Hz, 1H), 7.20 - 7.11 (m, 2H), 7.06 (t, J = 7.4 Hz, 1H), 6.89 (t, J = 7.4 Hz, 1H), 6.15 (s, 1H), 4.33 - 4.23 (m, 1H), 3.91 - 3.83 (m, 1H), 3.16 (t, J = 13.7 Hz, 1H), 2.79 (d, J = 15.2 Hz, 1H), 2.32 (s, 3H), 2.11 - 2.02 (m, 1H), 1.96 - 1.80 (m, J = 39.1 Hz, 3H), 1.65 - 1.58 (m, 2H). HRMS(ESI)(C 42 H 43 N 10 Pt2[M+H] + ): Calculated value 1077.2968, measured value 1077.2950
[0224] result The results of the instant work are shown below. Photophysical characterization of binuclear complexes in host compounds The Pt(II) binuclear complexes (Pt-1 and Pt-2) show intense deep blue to blue photoluminescence at 447–480 nm. The emission quantum yields are 0.74–0.82 (PMMA film, room temperature). The emission lifetimes are short, 1.3–2.0 μs, resulting in large radiative rate constants (3.7×10 5 s -1 ~6.3×10 5 s -1) or short radiative lifetimes (1.6-2.7 μs). The absorbance and emission data, and the associated photophysical data, are shown in Table 1 below.
[0225] [Table 1]
[0226] The vacuum-deposited devices using Pt-1 showed deep blue electroluminescence at various doping concentrations, with CIE(x,y) ranging from (0.15 to 0.16, 0.07 to 0.08). The maximum EQE of the device doped with 4 wt% Pt-1 was 12.14%, and the maximum CE was 7.53 cd / A. The appropriate blue index was 108.
[0227] [Table 2]
[0228] [Table 3]
[0229] Work (or research) is underway on (i) and (ii) below. (i) Further improving the thermal stability of the complex for convenient application in reduced pressure deposition manufacturing techniques (ii) Further clarifying the relationship between structure and properties could lead to improved photophysical attributes (e.g., emission bandwidth, color purity) that drive blue OLED applications.
[0230] Unless otherwise defined (or specified), all technical and scientific terms used in this disclosure have the same meaning as commonly understood by one of ordinary skill in the art to which the disclosed invention belongs. Publications mentioned in this disclosure and those described therein are specifically incorporated by reference. Furthermore, unless otherwise indicated, the use of the expression "weight percent (wt%)" means "weight / weight percent (wt / wt%)".
[0231] Those skilled in the art will recognize, or be able to ascertain (using no more than routine experimentation) many equivalents to the specific embodiments of the invention described in this disclosure. Such equivalents are intended to be encompassed by the scope of the following claims.
Claims
1. The following equation Ia: 【Chemistry 1】 Equation Ia [In the formula, The compound as a whole has a neutral, negative, or positive charge. A dashed line indicates the presence or absence of a connection. A and A' are independently substituted cycloalkyl, unsubstituted cycloalkyl, substituted cycloalkenyl, unsubstituted cycloalkenyl, substituted cycloalkynyl, unsubstituted cycloalkynyl, and substituted C 1 -C 20 Heterocyclyl, unsubstituted C 1 -C 20 Heterocyclyl, substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyaryl, unsubstituted polyaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, or combinations thereof; preferably, A and A' independently are substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyaryl, unsubstituted polyaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C 1 -C 20 Heterocyclyl, unsubstituted C 1 -C 20 Heterocyclines, or combinations thereof, X 5 and X 5’ is, independently, carbon or nitrogen and, independently, depending on the valence, is bonded to one hydrogen atom or not bonded to a hydrogen atom, preferably, X 5 and X 5’ is carbon, R 5 , R 6 , R 5’ and R 6’ These are independently absent or hydrogen, substituted alkyl, unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, substituted aryl, unsubstituted aryl, halogen, hydroxyl, thiol, cyano, nitro, unsubstituted alkoxy, substituted alkoxy, unsubstituted alloxy, substituted alloxy, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, unsubstituted alkylthio, substituted alkylthio, unsubstituted carbonyl, substituted carbonyl, unsubstituted carboxyl, substituted carboxyl, unsubstituted ester, substituted ester, substituted C 3 -C 20 Cycloalkyl, unsubstituted C 3 -C 20 Cycloalkyl, substituted C 1 -C 20 Heterocyclyl, unsubstituted C 1 -C 20 Heterocyclyl, substituted C 3 -C 20 Cycloalkenyl, unsubstituted C 3 -C 20 Cycloalkenyl, substituted C 3 -C 20 Cycloalkynyl, unsubstituted C 3 -C 20 It is either cycloalkynyl or R 5 and R 6 , R 5’ and R 6’ These, together with the atoms they bond to, form substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, and substituted C 1 -C 20 Heterocyclyl, unsubstituted C 1 -C 20 Heterocyclines, which form condensed combinations, or, preferably, R 5 , R 6 , R 5’ and R 6’ These are, independently, absent, hydrogen, substituted alkyl, unsubstituted alkyl, substituted aryl, and unsubstituted aryl. A 1 A 2 A 3 A 4 A 1’ A 2’ A 3’ and A 4’ These are, independently, either absent, hydrogen, deuterium, carbon, nitrogen, unsubstituted aryl, or unsubstituted aryl, and if present, independently, depending on their valence, they are bonded to 1, 2, 3, 4, or 5 hydrogen atoms, or are not bonded to any hydrogen atoms. R 1a , R 2a , R 3a , R 4a , R 1a’ , R 2a’ , R 3a’ and R 4a’ These are independently absent, hydrogen, deuterium, substituted alkyl, unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, substituted aryl, unsubstituted aryl, halogen, hydroxyl, thiol, cyano, nitro, unsubstituted alkoxy, substituted alkoxy, unsubstituted alloxy, substituted alloxy, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, unsubstituted alkylthio, substituted alkylthio, unsubstituted carbonyl, substituted carbonyl, unsubstituted carboxyl, substituted carboxyl, unsubstituted ester, substituted ester, substituted C 3 -C 20 Cycloalkyl, unsubstituted C 3 -C 20 Cycloalkyl, substituted C 1 -C 20 Heterocyclyl, unsubstituted C 1 -C 20 Heterocyclyl, substituted C 3 -C 20 Cycloalkenyl, unsubstituted C 3 -C 20 Cycloalkenyl, substituted C 3 -C 20 Cycloalkynyl, unsubstituted C 3 -C 20 Cycloalkynyl, unsubstituted C 1 -C 20 Heterocyclines, combinations of them formed by condensation (e.g., dibenzofuran-4-yl, dibenzofuran-3-yl, dibenzothiopen-4-yl, dibenzothiopen-3-yl, etc.), or R 1a and R 2a , R 2a and R 3a R 3a and R 4a R 1a’ and R 2a’ R 2a’ and R 3a’ R 3a’ and R 4a’ or combinations thereof, together with the atoms to which they are attached, form substituted cycloalkyl, unsubstituted cycloalkyl, substituted cycloalkenyl, unsubstituted cycloalkenyl, substituted cycloalkynyl, unsubstituted cycloalkynyl, substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyaryl, unsubstituted polyaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C 1 -C 20 heterocyclyl, unsubstituted C 1 -C 20 heterocyclyl, form combinations thereof that are fused, or R 1a and R 2a R 2a and R 3a R 3a and R 4a R 1a’ and R 2a’ R 2a’ and R 3a’ R 3a’ and R 4a’ or combinations thereof, together with the atoms to which they are attached, form substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyaryl, unsubstituted polyaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C 1 -C 20 heterocyclyl, unsubstituted C 1 -C 20 heterocyclyl, form combinations thereof that are fused, L 1 and L 1’ These are independently: substituted alkyl, unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, unsubstituted alkoxy, substituted alkoxy, unsubstituted alkylthio, substituted alkylthio, unsubstituted carbonyl, substituted carbonyl, unsubstituted carboxyl, substituted carboxyl, unsubstituted ester, substituted ester, unsubstituted ether, substituted ether, unsubstituted polyether, substituted polyether, substituted amino, unsubstituted amino, substituted amide, unsubstituted amide, substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyaryl, unsubstituted polyaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C 3 -C 20 Cycloalkyl, unsubstituted C 3 -C 20 Cycloalkyl, substituted C 1 -C 20 Heterocyclyl, unsubstituted C 1 -C 20 Heterocyclyl, substituted C 3 -C 20 Cycloalkenyl, unsubstituted C 3 -C 20 Cycloalkenyl, substituted C 3 -C 20 Cycloalkynyl, unsubstituted C 3 -C 20 [Cycloalkynyl, or a combination thereof] A compound having the structure.
2. L 1 and L 1’ The compound according to claim 1, wherein is independently a substituted alkyl or an unsubstituted alkyl.
3. L 1 and L 1’ This is independently of the substituted C 1 -C 10 Alkyl, unsubstituted C 1 -C 10 Alkyl, substituted C 2 -C 10 Alkyl or unsubstituted C 2 -C 10 Alkyl, preferably the substituted alkyl, the substituted C 1 -C 10 Alkyl, the substituted C 2 -C 10 Alkyl is composed of one or more alkyl substituents (e.g., methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl), one or more ether bonds, one or more amine groups (e.g., substituted or unsubstituted amines), one or more substituted aryl groups, one or more substituted heteroaryl groups, and one or more substituted C 3 -C 20 Cycloalkyl groups, one or more substituted C 1 -C 20 The compound according to claim 1, comprising a heterocyclyl group or a combination thereof.
4. R 1a , R 2a , R 3a , R 4a , R 1a’ , R 2a’ , R 3a’ and R 4a’ R is independently either absent, hydrogen, deuterium, substituted alkyl, unsubstituted alkyl, substituted aryl or unsubstituted aryl, or 1a and R 2a , R 2a and R 3a , R 3a and R 4a , R 1a’ and R 2a’ , R 2a’ and R 3a’ , R 3a’ and R 4a’ , or combinations thereof, together with the atoms they bond to, form substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyaryl, unsubstituted polyaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C 1 -C 20 Heterocyclyl, unsubstituted C 1 -C 20 The compound according to claim 1, wherein heterocyclyls form a condensed combination thereof.
5. The following formula IIa or formula IIb: 【Chemistry 2】 Formula IIa or 【Transformation 3】 Equation IIb [In the formula, A dashed line indicates the presence or absence of a connection. X 1 , X 2 , X 3 , X 4 , X 1’ , X 2’ , X 3’ and X 4’ If present, they are independently carbon, nitrogen, oxygen, or sulfur, and independently, depending on their valence, they are either bonded to one hydrogen atom or not bonded to a hydrogen atom. R 1 , R 2 , R 3 , R 4 , R 1’ , R 2’ , R 3’ and R 4’ These are, independently, absent, hydrogen, deuterium, substituted alkyl (e.g., trifluoromethyl), unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, substituted aryl (e.g., mesityl(2,4,6-trimethylphenyl), 3,5-di-tert-butylphenyl, 2,6-dimethylphenyl), unsubstituted aryl, halogen (e.g., fluorine), hydroxyl, thiol, cyano, nitro, unsubstituted alkoxy, substituted alkoxy, unsubstituted alloxy, substituted alloxy, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, unsubstituted alkylthio, substituted alkylthio, unsubstituted carbonyl, substituted carbonyl, unsubstituted carboxyl, substituted carboxyl, unsubstituted ester, substituted ester, substituted C 3 -C 20 Cycloalkyl, unsubstituted C 3 -C 20 Cycloalkyl, substituted C 1 -C 20 Heterocyclyl, unsubstituted C 1 -C 20 Heterocyclyl, substituted C 3 -C 20 Cycloalkenyl, unsubstituted C 3 -C 20 Cycloalkenyl, substituted C 3 -C 20 Cycloalkynyl or unsubstituted C 3 -C 20 It is either cycloalkynyl or R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 1’ and R 2’ , R 2’ and R 3’ , R 3’ and R 4’ , or combinations thereof, together with the atoms to which they are bonded, are substituted cycloalkyl, unsubstituted cycloalkyl, substituted cycloalkenyl, unsubstituted cycloalkenyl, substituted cycloalkynyl, unsubstituted cycloalkynyl, substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyaryl, unsubstituted polyaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C 1 -C 20 Heterocyclyl, unsubstituted C 1 -C 20 [They form heterocyclines, or combinations of them formed by condensation.] The compound according to claim 1, having the structure.
6. R 1 , R 2 , R 3 , R 4 , R 1’ , R 2’ , R 3’ and R 4’ These are, independently, absent, hydrogen, deuterium, substituted alkyl (e.g., trifluoromethyl), unsubstituted alkyl, substituted aryl (e.g., mesityl(2,4,6-trimethylphenyl), 3,5-di-tert-butylphenyl, 2,6-dimethylphenyl), unsubstituted aryl, halogen (e.g., fluorine), or R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 1’ and R 2’ , R 2’ and R 3’ , R 3’ and R 4’ , or combinations thereof, together with the atoms they bond to, form substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C 1 -C 20 Heterocyclyl, unsubstituted C 1 -C 20 The compound according to claim 5, which forms a heterocyclyl or a combination thereof.
7. The following formula IIIa or formula IIIb: 【Chemistry 4】 Formula IIIa or 【Transformation 5】 Formula IIIb [In the formula, The dashed line indicates whether a connection exists or not. A 5 A 6 A 5’ and A 6’ These are independently hydrogen, deuterium, unsubstituted alkyl, substituted alkyl, substituted aryl, unsubstituted aryl, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, and substituted C 1 -C 20 heterocyclyl or unsubstituted C 1 -C 20 It is a heterocycline, or preferably hydrogen, an unsubstituted alkyl, a substituted alkyl, deuterium, a substituted aryl, or an unsubstituted aryl. The compound according to claim 1, having the structure.
8. A 5 A 6 A 5’ and A 6’ The compound according to claim 7, wherein is hydrogen or deuterium.
9. A 5 A 6 A 5’ and A 6’ teeth, (i) Unsubstituted alkyl (e.g., unsubstituted C) 1 -C 10 Alkyl, unsubstituted C 1 -C 5 Alkyl or unsubstituted C 1 -C 3 Alkyl) or substituted alkyl (e.g., substituted C) 1 -C 10 Alkyl, substituted C 1 -C 5 Alkyl or substituted C 1 -C 3 Alkyl), or (ii) Hydrogen, substituted aryl, or unsubstituted aryl (However, A 5 and A 6 At least one of, or A 5’ and A 6’ The compound according to claim 7, wherein at least one of the elements is a substituted aryl or an unsubstituted aryl.
10. In formula IIa or formula IIIa, X 1 , X 2 , X 3 , X 4 , X 1’ , X 2’ , X 3’ and X 4’ The compound according to claim 5, wherein is carbon, and independently, depending on its valence, is either bonded to one hydrogen atom or not bonded to a hydrogen atom.
11. In formula IIa or formula IIIa, one or more X 1 , X 2 , X 3 and X 4 , and one or more X 1’ , X 2’ , X 3’ and X 4’ It is nitrogen, and X 1 , X 2 , X 3 , X 4 , X 1’ , X 2’ , X 3’ and X 4’ The compound according to claim 5, wherein, independently, depending on its valence, it is either bonded to one hydrogen atom or not bonded to a hydrogen atom.
12. In formula IIa or formula IIIa, X 2 and X 2’ It is nitrogen, and X 1 , X 3 , X 4 , X 1’ , X 3’ and X 4’ is carbon, X 1 , X 2 , X 3 , X 4 , X 1’ , X 2’ , X 3’ and X 4’ The compound according to claim 5, wherein, independently, depending on its valence, it is either bonded to one hydrogen atom or not bonded to a hydrogen atom.
13. In formula IIa or formula IIIa, R 1 , R 2 , R 3 , R 4 , R 1’ , R 2’ , R 3’ and R 4’ R is independently either absent, hydrogen, deuterium, substituted alkyl (e.g., trifluoromethyl), unsubstituted alkyl, substituted aryl (e.g., mesityl(2,4,6-trimethylphenyl), 3,5-di-tert-butylphenyl, 2,6-dimethylphenyl), unsubstituted aryl, halogen (e.g., fluorine), or R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 1’ and R 2’ , R 2’ and R 3’ , R 3’ and R 4’ , or combinations thereof, together with the atoms they bond to, form substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C 1 -C 20 Heterocyclyl, unsubstituted C 1 -C 20 The compound according to claim 5, which forms a heterocyclyl or a combination thereof.
14. In formula IIa or formula IIIa, R 1 , R 2 , R 3 , R 4 , R 1’ , R 2’ , R 3’ and R 4’ The compound according to claim 5, wherein is independently absent, or hydrogen, deuterium, a substituted alkyl (e.g., trifluoromethyl), an unsubstituted alkyl, a substituted aryl (e.g., mesityl(2,4,6-trimethylphenyl), 3,5-di-tert-butylphenyl, 2,6-dimethylphenyl), an unsubstituted aryl, or halogen (e.g., fluorine).
15. In formula IIa or formula IIIa, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 1’ and R 2’ , R 2’ and R 3’ , R 3’ and R 4’ , or combinations thereof, together with the atoms they bond to, form substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C 1 -C 20 Heterocyclyl, unsubstituted C 1 -C 20 The compound according to claim 5, which forms a heterocyclyl or a combination thereof.
16. In formula IIa or formula IIIa, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 1’ and R 2’ , R 2’ and R 3’ , R 3’ and R 4’ , or combinations thereof, together with the atoms they bond to, 【Transformation 6】 or 【Transformation 7】 [In the formula, Q 5 NR 14 , carbon, or sulfur, or oxygen; R 10 ~R 14 These are independently absent, hydrogen, substituted alkyl, unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, substituted aryl, unsubstituted aryl, halogen, hydroxyl, amino, amide, ether, thiol, cyano, nitro, unsubstituted alkoxy, substituted alkoxy, unsubstituted alloxy, substituted alloxy, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, unsubstituted carbonyl, substituted carbonyl, unsubstituted ester, substituted ester, substituted C 1 -C 20 heterocyclyl or unsubstituted C 1 -C 20 It is a heterocycline. The compound according to claim 5, which forms a compound.
17. Q 5 NR 14 , carbon, or sulfur, or oxygen, for example, oxygen; R 10 ~R 14 The compound according to claim 16, wherein is independently absent, hydrogen, a substituted alkyl, or an unsubstituted alkyl.
18. Q 5 is oxygen; R 10 ~R 14 The compound according to claim 16, wherein is hydrogen.
19. In formula IIb or formula IIIb, one or more X 1 , X 2 and X 3 , and one or more X 1’ , X 2’ and X 3’ is sulfur, oxygen, or nitrogen, and X 1 , X 2 , X 3 , X 1’ , X 2’ and X 3’ The compound according to claim 5, wherein, independently, depending on its valence, it is either bonded to one hydrogen atom or not bonded to a hydrogen atom.
20. In formula IIb or formula IIIb, X 1 , X 2 and X 3 one of, and X 1’ , X 2’ and X 3’ One of them is sulfur, X 1 , X 2 , X 3 , X 1’ , X 2’ and X 3’ The compound according to claim 5, wherein, independently, depending on its valence, it is either bonded to one hydrogen atom or not bonded to a hydrogen atom.
21. In formula IIb or formula IIIb, X 1 , X 2 and X 3 one of, and X 1’ , X 2’ and X 3’ One of them is oxygen, X 1 , X 2 , X 3 , X 1’ , X 2’ and X 3’ The compound according to claim 5, wherein, independently, depending on its valence, it is either bonded to one hydrogen atom or not bonded to a hydrogen atom.
22. In formula IIb or formula IIIb, R 1 , R 2 , R 3 , R 1’ , R 2’ and R 3’ Independently, is either absent, hydrogen, substituted alkyl, unsubstituted alkyl, substituted aryl, unsubstituted aryl, halogen, or R 1 and R 2 , R 2 and R 3 , R 1’ and R 2’ , R 2’ and R 3’ , or combinations thereof, together with the atoms they bond to, form substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C 1 -C 20 Heterocyclyl, unsubstituted C 1 -C 20 The compound according to claim 5, which forms a heterocyclyl or a combination thereof.
23. In formula IIb or formula IIIb, R 1 , R 2 , R 3 , R 1’ , R 2’ and R 3’ The compound according to claim 5, wherein is absent, hydrogen, or a combination thereof.
24. In formula IIb or formula IIIb, R 1 and R 2 , R 2 and R 3 , R 1’ and R 2’ , R 2’ and R 3’ , or combinations thereof, together with the atoms they bond to, form substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C 1 -C 20 Heterocyclyl, unsubstituted C 1 -C 20 The compound according to claim 5, which forms a heterocyclyl or a combination thereof.
25. In formula IIb or formula IIIb, R 1 and R 2 , R 2 and R 3 , R 1’ and R 2’ , R 2’ and R 3’ , or combinations thereof, together with the atoms they bond to, 【Transformation 8】 or 【Chemistry 9】 [In the formula, Q 5 NR 14 , carbon, or sulfur, or oxygen; R 10 ~R 14 These are independently absent, hydrogen, substituted alkyl, unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, substituted aryl, unsubstituted aryl, halogen, hydroxyl, amino, amide, ether, thiol, cyano, nitro, unsubstituted alkoxy, substituted alkoxy, unsubstituted alloxy, substituted alloxy, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, unsubstituted carbonyl, substituted carbonyl, unsubstituted ester, substituted ester, substituted C 1 -C 20 heterocyclyl or unsubstituted C 1 -C 20 It is a heterocycline. The compound according to claim 5, which forms a compound.
26. Q 5 NR 14 , carbon, sulfur or oxygen, for example, sulfur, R 10 ~R 14 The compound according to claim 25, wherein is independently absent, hydrogen, a substituted alkyl, or an unsubstituted alkyl.
27. Q 5 is sulfur; R 10 ~R 14 The compound according to claim 25, wherein is hydrogen.
28. In formula Ia, formula IIa, or formula IIb, the compound is the following formula IVa or formula IVb: 【Chemistry 10】 Formula IVa or 【Chemistry 11】 Formula IVb [In the formula, A 1 A 2 A 3 A 4 A 1’ A 2’ A 3’ and A 4’ These are, independently, carbon, nitrogen, oxygen, or sulfur, and independently, depending on their valence, either bonded to one hydrogen atom or not bonded to a hydrogen atom. X 1 , X 2 , X 3 , X 4 , X 1’ , X 2’ , X 3’ and X 4’ If present, it is independently carbon, nitrogen, oxygen, or sulfur, and independently, depending on its valence, is either bonded to one hydrogen atom or not bonded to a hydrogen atom. The compound according to claim 1, having the structure.
29. In formula IVa, A 1 A 2 A 3 A 4 A 1’ A 2’ A 3’ and A 4’ It is carbon, and independently, depending on its valence, is either bonded to one hydrogen atom or not bonded to a hydrogen atom, X 1 , X 2 , X 3 , X 4 , X 1’ , X 2’ , X 3’ and X 4’ The compound according to claim 28, wherein is carbon, and independently, depending on its valence, is either bonded to one hydrogen atom or not bonded to a hydrogen atom.
30. In formula IVa, R 1 , R 2 , R 3 , R 4 , R 1’ , R 2’ , R 3’ and R 4’ The compound according to claim 28, wherein is independently absent, hydrogen, deuterium, a substituted alkyl, an unsubstituted alkyl, a substituted aryl, an unsubstituted aryl, or a halogen.
31. In formula IVa, R 1a , R 2a , R 3a , R 4a , R 1a’ , R 2a’ , R 3a’ and R 4a’ R is independently either absent, hydrogen, deuterium, substituted alkyl, unsubstituted alkyl, substituted aryl, or unsubstituted aryl, or 1a and R 2a , R 2a and R 3a , R 3a and R 4a , R 1a’ and R 2a’ , R 2a’ and R 3a’ , R 3a’ and R 4a’ The compound according to claim 28, wherein the compounds, or combinations thereof, together with the atoms to which they are bonded, form a substituted aryl or an unsubstituted aryl.
32. In formula IVa, R 1a and R 2a , R 3a and R 4a , R 1a’ and R 2a’ , R 3a’ and R 4a’ The compound according to claim 28, wherein the atoms they bond to together form a substituted or unsubstituted aryl group.
33. In formula Ia, formula IIa, or formula IVa, one or more A 1 A 2 A 3 and A 4 is nitrogen, and 1 or more A 1’ A 2’ A 3’ and A 4’ It is nitrogen, and A 1 A 2 A 3 A 4 A 1’ A 2’ A 3’ and A 4’ Independently, depending on its valence, it is either bonded to one hydrogen atom or not bonded to a hydrogen atom, X 1 , X 2 , X 3 , X 4 , X 1’ , X 2’ , X 3’ and X 4’ The compound according to claim 1, wherein is carbon, and independently, depending on its valence, is either bonded to one hydrogen atom or not bonded to a hydrogen atom.
34. Regarding formula IVa, R 1 , R 2 , R 3 , R 4 , R 1’ , R 2’ , R 3’ and R 4’ The compound according to claim 33, wherein is independently absent, hydrogen, deuterium, a substituted alkyl, an unsubstituted alkyl, a substituted aryl (e.g., mesityl(2,4,6-trimethylphenyl), 3,5-di-tert-butylphenyl, 2,6-dimethylphenyl), an unsubstituted aryl, or a halogen (e.g., fluorine).
35. R 1a , R 2a , R 3a , R 4a , R 1a’ , R 2a’ , R 3a’ and R 4a’ The compound according to claim 33, wherein is independently absent, or hydrogen, deuterium, a substituted alkyl, an unsubstituted alkyl, a substituted aryl, or an unsubstituted aryl (e.g., phenyl).
36. In formula IVa, A 1 A 2 A 3 and A 4 One of them is nitrogen, and the other three are carbon, A 1’ A 2’ A 3’ and A 4’ One of them is nitrogen, and the other three are carbon, A 1 A 2 A 3 A 4 A 1’ A 2’ A 3’ and A 4’ The compound according to claim 33, wherein, independently, depending on its valence, it is either bonded to one hydrogen atom or not bonded to a hydrogen atom.
37. In formula IVa, A 1 A 2 A 3 and A 4 Two of them are nitrogen, and the other two are carbon, A 1’ A 2’ A 3’ and A 4’ Two of them are nitrogen, and the other two are carbon, A 1 A 2 A 3 A 4 A 1’ A 2’ A 3’ and A 4’ The compound according to claim 33, wherein, independently, depending on its valence, it is either bonded to one hydrogen atom or not bonded to a hydrogen atom.
38. In formula Ia, formula IIa, or formula IVa, one or more A 1 A 2 A 3 and A 4 is oxygen, nitrogen, or sulfur, and one or more A 1’ A 2’ A 3’ and A 4’ is oxygen, nitrogen, or sulfur, A 1 A 2 A 3 A 4 A 1’ A 2’ A 3’ and A 4’ Each atom is independently bonded to one hydrogen atom, or not bonded to a hydrogen atom, depending on its valence, and contains one or more X atoms. 1 , X 2 , X 3 , X 4 , X 1’ , X 2’ , X 3’ and X 4’ is oxygen, nitrogen, or sulfur, X 1 , X 2 , X 3 , X 4 , X 1’ , X 2’ , X 3’ and X 4’ The compound according to claim 1, wherein, independently, depending on its valence, it is either bonded to one hydrogen atom or not bonded to a hydrogen atom.
39. In formula IVa, R 1 , R 2 , R 3 , R 4 , R 1’ , R 2’ , R 3’ and R 4’ The compound according to claim 38, wherein is independently absent, or hydrogen, deuterium, a substituted alkyl, an unsubstituted alkyl, a substituted aryl, an unsubstituted aryl, or a halogen (e.g., fluorine).
40. R 1a , R 2a , R 3a , R 4a , R 1a’ , R 2a’ , R 3a’ and R 4a’ The compound according to claim 38, wherein is independently absent, hydrogen, deuterium, a substituted alkyl, an unsubstituted alkyl, a substituted aryl, or an unsubstituted aryl.
41. In formula IVa, one or more A 1 A 2 A 3 and A 4 is nitrogen, and 1 or more A 1’ A 2’ A 3’ and A 4’ It is nitrogen, and A 1 A 2 A 3 A 4 A 1’ A 2’ A 3’ and A 4’ Each atom is independently bonded to one hydrogen atom, or not bonded to a hydrogen atom, depending on its valence, and contains one or more X atoms. 1 , X 2 , X 3 , X 4 , X 1’ , X 2’ , X 3’ and X 4’ It is nitrogen, and X 1 , X 2 , X 3 , X 4 , X 1’ , X 2’ , X 3’ and X 4’ The compound according to claim 38, wherein, independently, depending on its valence, it is either bonded to one hydrogen atom or not bonded to a hydrogen atom.
42. In formula IVa, A 1 A 2 A 3 and A 4 One of them is nitrogen, and the other three are carbon, A 1’ A 2’ A 3’ and A 4’ One of them is nitrogen, and the other three are carbon, A 1 A 2 A 3 A 4 A 1’ A 2’ A 3’ and A 4’ Independently, depending on its valence, it is either bonded to one hydrogen atom or not bonded to a hydrogen atom, X 1 , X 2 , X 3 and X 4 One of them is nitrogen, and the other three are carbon, X 1’ , X 2’ , X 3’ and X 4’ One of them is nitrogen, and the other three are carbon, X 1 , X 2 , X 3 , X 4 , X 1’ , X 2’ , X 3’ and X 4’ The compound according to claim 38, wherein, independently, depending on its valence, it is either bonded to one hydrogen atom or not bonded to a hydrogen atom.
43. The following structure: 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 The compound according to claim 1, having the following characteristics.
44. An organic electronic component comprising the compound described in any one of claims 1 to 43.
45. The organic electronic component according to claim 44, wherein the organic electronic component is an organic light-emitting diode (OLED) or an electrochemiluminescent cell (LEEC).
46. The organic electronic component according to claim 44, wherein the compound is contained in the light-emitting layer.
47. A-scatter, Cathode and, Hole transport region, In the field of electron transport and It further comprises, The hole transport region includes a hole injection layer and / or a hole transport layer, and further, optionally, an electron barrier layer. The electron transport region includes an electron transport layer and / or an electron injection layer, and further, optionally, a hole blocking layer. The light-emitting layer is positioned between the anode and the cathode. The hole transport region is located between the anode and the light-emitting layer. The electron transport region is located between the cathode and the light-emitting layer. The organic electronic component according to claim 44.
48. The organic electronic component according to claim 46, wherein the light-emitting layer is formed by vacuum deposition, spin coating, or ink printing (e.g., inkjet printing or roll-to-roll printing).
49. A light-emitting layer comprising the compound described in any one of claims 1 to 43.
50. The compound further comprises a pure organic emitter, and the compound is (i) Acting as a sensor for transferring energy to the pure organic emitter, (ii) Having a singlet state higher than that of the pure organic emitter, The light-emitting layer according to claim 49.
51. An OLED comprising the light-emitting layer described in claim 49.
52. A device comprising an OLED according to claim 51, wherein the device is selected from stationary visual display units, mobile visual display units, illumination units, keyboards, cloths, ornaments, garment accessories, wearable devices, medical monitoring devices, wallpapers, tablet computers, laptops, advertisement panels, panel display units, household appliances, or office appliances.