d10 Metal Carbene Complexes for OLED Applications

Abstract

This disclosure describes two-coordinate d10 metal carbene complexes that comprise (i) Cu(I), Ag(I) or Au(I), (ii) a pyrazine- or pyridine-fused NHC ligand, and (iii) a carbazole, pyrido[2,3-b]indole or pyrido[3,4-b]indole ligand. The emission properties of the compounds can be tuned by thermally activated delayed fluorescence. The emission color of the complexes can be tuned by varying the donor strength through the use of carbazole. Methods of using the complexes are also described.

Description

[Technical field]

[0001] (CROSS REFERENCE TO RELATED APPLICATIONS) This application claims the benefit of and priority to U.S. Provisional Application No. 63 / 282,496, filed November 23, 2021, which is incorporated by reference in its entirety.

[0002] FIELD OF THEINVENTION The invention of the present disclosure is generally in the field of luminescent d10 metal carbene complexes (or d10 metal carbene complexes or d10 metal-carbene complexes), in particular d10 metal carbene complexes (or d10 metal carbene complexes or d10 metal-carbene complexes) comprising: (i) pyrazine-fused N-heterocyclic carbene ligands (or pyrazine-fused N-heterocyclic carbene ligands) or pyridine-fused N-heterocyclic carbene ligands (or pyridine-fused N-heterocyclic carbene ligands), and (ii) Carbazole ligands or alpha (α)-, beta (β)-, gamma (γ)- or delta (δ)-carboline ligands. The invention of the present disclosure also resides in the use of such complexes in 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 pure organic-based materials because of their potential for improved luminescence efficiency and device stability compared to pure organic-based materials.

[0004] Currently, cyclometallated iridium(III) and Pt(II) phosphors (or phosphors) are among the most competitive candidates for commercial OLED emitters. Nevertheless, the development of metallic or organic thermally activated delayed fluorescence (TADF) emitters is still lagging behind, mainly due to their lower stability, which may affect the device lifetime. The device performance as well as the operation stability / lifetime of metal-based OLEDs need to be enhanced in practical applications. Several studies have described d10 complexes (or d10 complexes or d10 complexes) for use as OLED emitters. Research includes: U.S. Patent No. 9,773,986 (Thompson et al.); European Patent Application Publication No. 3,489,243 (Thompson et al.); U.S. Patent Application Publication No. 2015 / 0108451 (Thompson et al.), and U.S. Patent Application Publication No. 2019 / 0161504 (Thompson et al.); and China (CN) No. 112794863 Nevertheless, these studies did not report on device longevity (or lifetime) results. Further work has involved complexes of Cu(I), Ag(I) or Au(I) containing carbene ligands and carbazoles (see, for example, the following references): Hamze et al., Science 2019, 363, 601-606; Shi et al., J. Am. Chem. Soc. 2019, 141, 3576-3588; Hamze et al., J. Am. Chem. Soc. 2019, 141, 21, 8616-8626; Li et al., Angew. Chem. Int. Ed. 2020, 59,8210-8217; and Hamze et al., Front. Chem. 2020, 8:401 However, some of such complexes have shown phosphorescent character, which results in a lower radiative decay rate. For example, the complexes IPr-Cu-Cz and IMes-Cu-Cz (Angew. Chem. Int. Ed. 2020, 59, 8210-8217) exhibited long-lived room temperature phosphorescence with lifetimes in the millisecond range. Summary of the Invention [Problem to be solved by the invention]

[0005] Therefore, there is still a need to develop improved and more efficient transition metal complexes, so that the efficiency of OLED-containing products can be improved.

[0006] It is therefore an object of the present invention to provide new and improved luminescent transition metal two-coordinate d10 metal-containing complexes. [Means for solving the problem]

[0007] Summary of the Invention Disclosed is a two-coordinate (or two-conformation or two-coordination) d10 metal carbene complex (or d10 metal carbene complex or d10 metal-carbene complex), which comprises the following (i) to (iii): (i) Cu(I), Ag(I) or Au(I) (ii) pyrazine-fused N-heterocyclic carbene (NHC) ligands or pyridine-fused N-heterocyclic carbene ligands, and (iii) Carbazole ligands, pyrido[2,3-b]indole ligands or pyrido[3,4-b]indole ligands. The radiative properties of such compounds can be tuned (or controlled) by TADF. Furthermore, the emission color of such compounds can be tuned (changing the donor strength) by using carbazoles, pyrido[2,3-b]indoles, or pyrido[3,4-b]indoles.

[0008] The compound has the structure of Formula V: [ka] Formula V D is carbon. T, J and W are independently carbon or nitrogen, where at least one of T, J and W is nitrogen, where when T is carbon, J is nitrogen, or when T is nitrogen, J is carbon, and T, J and W are bonded to one or no hydrogen atoms according to valency. Each Ra is independently hydrogen, unsubstituted alkyl, or substituted alkyl. Each Rb is independently unsubstituted alkyl or substituted alkyl. X and Y are nitrogen. L is either absent or a single bond. CY3 and CY4 are independently unsubstituted aryl, substituted aryl, unsubstituted heteroaryl, substituted heteroaryl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 cycloalkenyl, or fused combinations thereof. R1 and R2 are hydrogen. Alternatively, R1, J, D and R2 together form an unsubstituted aryl, a substituted aryl, an unsubstituted heteroaryl or a substituted heteroaryl.

[0009] In some embodiments, the compound has a structure of Formula VIII: [ka] Formula VIII (i) M=Cu(I);W=N;Ra=H;U=CH;V=V''=carbon;Rv=H;R7=R8=H; (ii) M=Cu(I);W=N;Ra=H;U=CH;V=V''=carbon;Rv=H;R7=H;R8=CN; (iii) M=Cu(I); W=N; Ra=H; U=CH; V=V″=carbon; Rv=H; R7=R8=tert-butyl; (iv) M=Cu(I); W=N; Ra=H; U=CH; V=V″=carbon; Rv=H; R7=R8=phenyl; (v) M=Cu(I); W=N; Ra=H; U=CH; V=N; V″=carbon; Rv=absent (or absent); R7=R8=H; (vi) M=Cu(I); W=U=CH; V=V″=carbon; Rv=H; Ra=iso-propyl; R7=R8=H; (vii) M=Cu(I); W=N; Ra=H; U=CH; V=V''=carbon; R8=H; Rv and R7 together are [ka] Form (or generate); (viii) M=Cu(I); W=U=CH; Ra=iso-propyl; V=V″=carbon; R8=H; Rv and R7 together are [ka] Form (or generate); (ix) M=Cu(I);W=N;Ra=H;U=CH;V=V''=carbon;Rv=H;R7=R8=H; (x) M=Cu(I);W=N;Ra=H;U=CH;V=V''=carbon;Rv=H;R7=H;R8=F; (xi) M=Cu(I); W=N; Ra=H; U=CH; V=V″=carbon; Rv=H; R7=R8=methyl; (xii) M=Au(I); W=N; Ra=H; U=CH; V=carbon; Rv=H; V''=carbon; R7=R8=H; (xiii) M=Au(I); W=N; Ra=H; U=CH; V=carbon; Rv=H; V''=carbon; R7=H, R8=CN; (xiv) M=Au(I); W=N; Ra=H; U=N; V=carbon; Rv=H; V''=carbon; R7=R8=H; (xv) M=Au(I);W=U=CH;V=carbon;Rv=H;;Ra=iso-propyl;V''=carbon;R7=R8=H; (xvi) M=Au(I); W=N; Ra=H; U=CH; V=N; Rv=absent (or absent or absent); V″=carbon; R7=R8=H; (xvii) M=Au(I);W=N;Ra=H;U=CH;V=V''=carbon;Rv=H;R7=R8=CN; (xviii) M=Au(I); W=N; Ra=hydrogen; U=CH; V=V″=carbon; R8=H; Rv and R7 together are [ka] Form (or generate); (xix) M=Au(I); W=U=CH; Ra=iso-propyl; V=V″=carbon; Rv=H; R7=R8=tert-butyl; (xx) M=Au(I); W=U=CH; Ra=iso-propyl; V=V″=carbon; Rv=H; R7=H; R8=F; (xxi) M=Au(I); W=N; U=CH; Ra=H; V=V''=carbon; Rv=H; R7=R8=H; (xxii) M=Au(I); W=N; U=CH; Ra=H; V=V″=carbon; Rv=H; R7=R8=tert-butyl; (xxiii) M=Ag(I);W=N;U=CH;Ra=H;V=V''=carbon;Rv=H;R7=R8=H; For (i), (ii), (iii), (iv), (v), (vi), (vii), (viii), (xii), (xiii), (xiv), (xv), (xvi), (xvii), (xviii), (xix), (xx) and (xxiii), the dashed line indicates the absence (or absence) of a bond. For (ix), (x), (xi), (xxi) and (xxii), the dashed line indicates the existence (or presence) of a bond.

[0010] The compounds of the present disclosure may be included in organic light emitting devices (or organic light emitting apparatus or organic light emitting devices) for use in commercial uses (or applications). [Brief description of the drawings]

[0011] [Figure 1] Figure 1 shows the chemical structures of metal carbene complexes designated Cu1, Cu2, Cu3, Cu4, Cu5, Cu6, Cu7, Cu8, Cu9, Cu10, Cu11, Au1, Au2, Au3, Au4, Au5, Au6, Au7, Au8, Au9, Au10, Au11 and Ag1. [Figure 2A] FIG. 2A shows the crystal structure of Au1 shown in FIG. [Figure 2B] FIG. 2B shows the crystal structure of Au4 shown in FIG. [Figure 2C] FIG. 2C shows the crystal structure of Au8 shown in FIG. [Figure 2D] FIG. 2D shows the crystal structure of Au9 shown in FIG. [Figure 2E] FIG. 2E shows the crystal structure of Cu3 shown in FIG. [Figure 2F] FIG. 2F shows the crystal structure of Cu6 shown in FIG. [Figure 3A]Figure 3A is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of Cu1-based devices (doping concentrations 2-8 wt / wt%). Device structure: ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:TPBi:Cu1(20 nm) / TPBi(50 nm) / LiF(1 nm) / Al(100 nm). [Figure 3B] Figure 3B is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of Cu1-based devices (doping concentrations 2-8 wt / wt%). Device structure: ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:TPBi:Cu1(20 nm) / TPBi(50 nm) / LiF(1 nm) / Al(100 nm). [Figure 3C] Figure 3C is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of Cu1-based devices (doping concentrations 2-8 wt / wt%). Device structure: ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:TPBi:Cu1(20 nm) / TPBi(50 nm) / LiF(1 nm) / Al(100 nm). [Figure 3D] Figure 3D is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of Cu1-based devices (doping concentrations 2-8 wt / wt%). Device structure: ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:TPBi:Cu1(20 nm) / TPBi(50 nm) / LiF(1 nm) / Al(100 nm). [Figure 4A]Figure 4A is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of the devices of Cu2 (doping concentration 2-6 wt / wt%). Device structure: ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:DPEPO:Cu2(20 nm) / DPEPO(10 nm) / TPBi(40 nm) / LiF(1 nm) / Al(100 nm). [Figure 4B] Figure 4B is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of the devices of Cu2 (doping concentration 2-6 wt / wt%). Device structure: ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:DPEPO:Cu2(20 nm) / DPEPO(10 nm) / TPBi(40 nm) / LiF(1 nm) / Al(100 nm). [Figure 4C] Figure 4C is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of the devices of Cu2 (doping concentration 2-6 wt / wt%). Device structure: ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:DPEPO:Cu2(20 nm) / DPEPO(10 nm) / TPBi(40 nm) / LiF(1 nm) / Al(100 nm). [Figure 4D] Figure 4D is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of the devices of Cu2 (doping concentration 2-6 wt / wt%). Device structure: ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:DPEPO:Cu2(20 nm) / DPEPO(10 nm) / TPBi(40 nm) / LiF(1 nm) / Al(100 nm). [Figure 5A]Figure 5A is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of the device for Cu3 (doping concentration 2-6 wt / wt%). Device structure: ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:TPBi:Cu3(20 nm) / TPBi(50 nm) / LiF(1 nm) / Al(100 nm). [Figure 5B] Figure 5B is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of the device for Cu3 (doping concentration 2-6 wt / wt%). Device structure: ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:TPBi:Cu3(20 nm) / TPBi(50 nm) / LiF(1 nm) / Al(100 nm). [Figure 5C] Figure 5C is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of the devices with Cu3 (doping concentrations 2-6 wt / wt%). Device structure: ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:TPBi:Cu3(20 nm) / TPBi(50 nm) / LiF(1 nm) / Al(100 nm). [Figure 5D] Figure 5D is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of the devices with Cu3 (doping concentrations 2-6 wt / wt%). Device structure: ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:TPBi:Cu3(20 nm) / TPBi(50 nm) / LiF(1 nm) / Al(100 nm). [Figure 6A] Figure 6A is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of devices with Au1 (doping concentrations 2-6 wt / wt%). Device structure: ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:TPBi:Au1(20 nm) / TPBi(50 nm) / LiF(1 nm) / Al(100 nm). [Figure 6B] Figure 6B is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of the device of Au1 (doping concentration 2-6 wt / wt%). Device structure: ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:TPBi:Au1(20 nm) / TPBi(50 nm) / LiF(1 nm) / Al(100 nm). [Figure 6C] Figure 6C is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of the device of Au1 (doping concentration 2-6 wt / wt%). Device structure: ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:TPBi:Au1(20 nm) / TPBi(50 nm) / LiF(1 nm) / Al(100 nm). [Figure 6D] Figure 6D is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of the device of Au1 (doping concentration 2-6 wt / wt%). Device structure: ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:TPBi:Au1(20 nm) / TPBi(50 nm) / LiF(1 nm) / Al(100 nm). [Figure 7A] Figure 7A is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of the Au2 devices (doping concentrations 2-6 wt / wt%). Device structure (I): ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:TPBi:Au2(20 nm) / TPBi(50 nm) / LiF(1 nm) / Al(100 nm). [Figure 7B]Figure 7B is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of the Au2 devices (doping concentrations 2-6 wt / wt%). Device structure (I): ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:TPBi:Au2(20 nm) / TPBi(50 nm) / LiF(1 nm) / Al(100 nm). [Figure 7C] Figure 7C is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of the Au2 devices (doping concentrations 2-6 wt / wt%). Device structure (I): ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:TPBi:Au2(20 nm) / TPBi(50 nm) / LiF(1 nm) / Al(100 nm). [Figure 7D] Figure 7D is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of the Au2 devices (doping concentrations 2-6 wt / wt%). Device structure (I): ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:TPBi:Au2(20 nm) / TPBi(50 nm) / LiF(1 nm) / Al(100 nm). [Figure 8A] Figure 8A is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of the Au2 devices (doping concentrations 2-8 wt / wt%). Device structure (II): ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:DPEPO:Au2(20 nm) / DPEPO(10 nm) / TPBi(40 nm) / LiF(1 nm) / Al(100 nm). [Figure 8B]Figure 8B is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of the Au2 devices (doping concentrations 2-8 wt / wt%). Device structure (II): ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:DPEPO:Au2(20 nm) / DPEPO(10 nm) / TPBi(40 nm) / LiF(1 nm) / Al(100 nm). [Figure 8C] Figure 8C is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of the Au2 devices (doping concentrations 2-8 wt / wt%). Device structure (II): ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:DPEPO:Au2(20 nm) / DPEPO(10 nm) / TPBi(40 nm) / LiF(1 nm) / Al(100 nm). [Figure 8D] Figure 8D is a line graph (or line graph) showing the electroluminescence spectrum and performance characteristics of the Au2 devices (doping concentrations 2-8 wt / wt%). Device structure (II): ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:DPEPO:Au2(20 nm) / DPEPO(10 nm) / TPBi(40 nm) / LiF(1 nm) / Al(100 nm). [Figure 9] Figure 9 is a line graph showing the emission spectrum of Cu4. [Figure 10] Figure 10 is a line graph showing the emission spectrum of Au3. [Figure 11] Figure 11 is a line graph showing the emission spectrum of Cu5. [Figure 12A] Figure 12A is a line graph showing the emission spectrum of Cu6. [Figure 12B] Figure 12B is a line graph showing the emission spectrum of Au4. [Figure 13A]FIG. 13A is a line graph (or line graph) showing the device data of Cu2 in Table 5b, the EL spectrum and performance characteristics of the device of Cu2 (doping concentration 2 wt / wt%). Device structure: ITO / HAT-CN(5 nm) / PT-301(160 nm) / PT-603I(5 nm) / Cu2:LLP604(20 nm) / PT74M(5 nm) / LET321:Liq(1:1,25 nm) / Liq(1 nm) / Al(100 nm). [Figure 13B] FIG. 13B is a line graph (or line graph) showing the device data of Cu2 in Table 5b, the EL spectrum and performance characteristics of the device of Cu2 (doping concentration 2 wt / wt%). Device structure: ITO / HAT-CN(5 nm) / PT-301(160 nm) / PT-603I(5 nm) / Cu2:LLP604(20 nm) / PT74M(5 nm) / LET321:Liq(1:1,25 nm) / Liq(1 nm) / Al(100 nm). [Figure 13C] FIG. 13C is a line graph (or line graph) showing the device data of Cu2 in Table 5b, the EL spectrum and performance characteristics of the device of Cu2 (doping concentration 2 wt / wt%). Device structure: ITO / HAT-CN(5 nm) / PT-301(160 nm) / PT-603I(5 nm) / Cu2:LLP604(20 nm) / PT74M(5 nm) / LET321:Liq(1:1,25 nm) / Liq(1 nm) / Al(100 nm). [Figure 14A] Figure 14A is a line graph (or line graph) showing the EL spectrum and performance characteristics of the device of Cu3 (doping concentration 2-6 wt / wt%). Device structure (II): ITO / HAT-CN(5 nm) / PT-301(160 nm) / EB(5 nm) / Cu3:RH(40 nm) / HB(5 nm) / ZADN:Liq(35:65,35 nm) / Liq(1 nm) / Al(100 nm). [Figure 14B]Figure 14B is a line graph (or line graph) showing the EL spectrum and performance characteristics of the device for Cu3 (doping concentration 2-6 wt / wt%). Device structure (II): ITO / HAT-CN(5 nm) / PT-301(160 nm) / EB(5 nm) / Cu3:RH(40 nm) / HB(5 nm) / ZADN:Liq(35:65,35 nm) / Liq(1 nm) / Al(100 nm). [Figure 14C] Figure 14C is a line graph (or line graph) showing the EL spectrum and performance characteristics of the device of Cu3 (doping concentration 2-6 wt / wt%). Device structure (II): ITO / HAT-CN(5 nm) / PT-301(160 nm) / EB(5 nm) / Cu3:RH(40 nm) / HB(5 nm) / ZADN:Liq(35:65,35 nm) / Liq(1 nm) / Al(100 nm). [Figure 14D] Figure 14D is a line graph (or line graph) showing the EL spectrum and performance characteristics of the device of Cu3 (doping concentration 2-6 wt / wt%). Device structure (II): ITO / HAT-CN(5 nm) / PT-301(160 nm) / EB(5 nm) / Cu3:RH(40 nm) / HB(5 nm) / ZADN:Liq(35:65,35 nm) / Liq(1 nm) / Al(100 nm). [Figure 15A] Figure 15A is a line graph (or line graph) showing the EL spectrum and performance characteristics of the device for Cu4 (doping concentration 2-6 wt / wt%). Device structure (I): ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:TPBi:Cu4(20 nm) / TPBi(50 nm) / LiF(1 nm) / Al(100 nm). [Figure 15B]Figure 15B is a line graph (or line graph) showing the EL spectrum and performance characteristics of the device for Cu4 (doping concentration 2-6 wt / wt%). Device structure (I): ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:TPBi:Cu4(20 nm) / TPBi(50 nm) / LiF(1 nm) / Al(100 nm). [Figure 15C] Figure 15C is a line graph (or line graph) showing the EL spectrum and performance characteristics of the device for Cu4 (doping concentration 2-6 wt / wt%). Device structure (I): ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:TPBi:Cu4(20 nm) / TPBi(50 nm) / LiF(1 nm) / Al(100 nm). [Figure 15D] Figure 15D is a line graph (or line graph) showing the EL spectrum and performance characteristics of the device for Cu4 (doping concentration 2-6 wt / wt%). Device structure (I): ITO / HAT-CN(5 nm) / TAPC(40 nm) / TCTA(10 nm) / TCTA:TPBi:Cu4(20 nm) / TPBi(50 nm) / LiF(1 nm) / Al(100 nm). [Figure 16A] Figure 16A is a line graph (or line graph) showing the EL spectrum and performance characteristics of the device of Cu4 (doping concentration 2-6 wt / wt%). Device structure (II): ITO / HAT-CN(5 nm) / PT-301(160 nm) / PT-603I(5 nm) / Cu4:LLP604(20 nm) / PT74M(5 nm) / LET321:Liq(1:1,25 nm) / Liq(1 nm) / Al(100 nm). [Figure 16B]Figure 16B is a line graph (or line graph) showing the EL spectrum and performance characteristics of the device of Cu4 (doping concentration 2-6 wt / wt%). Device structure (II): ITO / HAT-CN(5 nm) / PT-301(160 nm) / PT-603I(5 nm) / Cu4:LLP604(20 nm) / PT74M(5 nm) / LET321:Liq(1:1,25 nm) / Liq(1 nm) / Al(100 nm). [Figure 16C] Figure 16C is a line graph (or line graph) showing the EL spectrum and performance characteristics of the device of Cu4 (doping concentration 2-6 wt / wt%). Device structure (II): ITO / HAT-CN(5 nm) / PT-301(160 nm) / PT-603I(5 nm) / Cu4:LLP604(20 nm) / PT74M(5 nm) / LET321:Liq(1:1,25 nm) / Liq(1 nm) / Al(100 nm). [Figure 16D] Figure 16D is a line graph (or line graph) showing the EL spectrum and performance characteristics of the device of Cu4 (doping concentration 2-6 wt / wt%). Device structure (II): ITO / HAT-CN(5 nm) / PT-301(160 nm) / PT-603I(5 nm) / Cu4:LLP604(20 nm) / PT74M(5 nm) / LET321:Liq(1:1,25 nm) / Liq(1 nm) / Al(100 nm). [Figure 17A] Figure 17A is a line graph (or line graph) showing the EL spectrum and performance characteristics of the device of Au2 (doping concentration 2-8 wt / wt%). Device structure (III): ITO / HAT-CN(5 nm) / PT-301(160 nm) / PT-603I(5 nm) / Au2:LLP604(20 nm) / PT74M(5 nm) / LET321:Liq(1:1,25 nm) / Liq(1 nm) / Al(100 nm). [Figure 17B]Figure 17B is a line graph (or line graph) showing the EL spectrum and performance characteristics of the device of Au2 (doping concentration 2-8 wt / wt%). Device structure (III): ITO / HAT-CN(5 nm) / PT-301(160 nm) / PT-603I(5 nm) / Au2:LLP604(20 nm) / PT74M(5 nm) / LET321:Liq(1:1,25 nm) / Liq(1 nm) / Al(100 nm). [Figure 17C] Figure 17C is a line graph (or line graph) showing the EL spectrum and performance characteristics of the device of Au2 (doping concentration 2-8 wt / wt%). Device structure (III): ITO / HAT-CN(5 nm) / PT-301(160 nm) / PT-603I(5 nm) / Au2:LLP604(20 nm) / PT74M(5 nm) / LET321:Liq(1:1,25 nm) / Liq(1 nm) / Al(100 nm). [Figure 17D] Figure 17D is a line graph (or line graph) showing the EL spectrum and performance characteristics of the device of Au2 (doping concentration 2-8 wt / wt%). Device structure (III): ITO / HAT-CN(5 nm) / PT-301(160 nm) / PT-603I(5 nm) / Au2:LLP604(20 nm) / PT74M(5 nm) / LET321:Liq(1:1,25 nm) / Liq(1 nm) / Al(100 nm). [Figure 18] Figure 18 is a line graph (or line graph) showing the emission spectrum of Cu7 (in MCP film). [Figure 19] Figure 19 is a line graph (or line graph) showing the emission spectrum of Cu8 (in MCP film). [Figure 20] Figure 20 is a line graph (or line graph) showing the emission spectrum of Cu9 (in degassed toluene and in MCP film). [Figure 21] Figure 21 is a line graph showing the emission spectrum of Au7 (2 wt / wt% in PMMA film). [Figure 22A]FIG. 22A is a line graph (or line graph) showing the EL spectrum and performance characteristics of a device of Cu6 (TCTA:DPEPO (co-host) (doping concentration 2-6 wt / wt%). Device structure: ITO / HAT-CN (5 nm) / TAPC (40 nm) / TCTA (10 nm) / TCTA:DPEPO:Cu6 (20 nm) / DPEPO (10 nm) / TPBi (40 nm) / LiF (1.2 nm) / Al (100 nm). [Figure 22B] Figure 22B is a line graph (or line graph) showing the EL spectrum and performance characteristics of the device of Cu6 (TCTA:DPEPO (co-host) (doping concentration 2-6 wt / wt%). Device structure: ITO / HAT-CN (5 nm) / TAPC (40 nm) / TCTA (10 nm) / TCTA:DPEPO:Cu6 (20 nm) / DPEPO (10 nm) / TPBi (40 nm) / LiF (1.2 nm) / Al (100 nm). [Figure 22C] Figure 22C is a line graph (or line graph) showing the EL spectrum and performance characteristics of the device of Cu6 (TCTA:DPEPO (co-host) (doping concentration 2-6 wt / wt%). Device structure: ITO / HAT-CN (5 nm) / TAPC (40 nm) / TCTA (10 nm) / TCTA:DPEPO:Cu6 (20 nm) / DPEPO (10 nm) / TPBi (40 nm) / LiF (1.2 nm) / Al (100 nm). [Figure 22D] Figure 22D is a line graph (or line graph) showing the EL spectrum and performance characteristics of the device of Cu6 (TCTA:DPEPO (co-host) (doping concentration 2-6 wt / wt%). Device structure: ITO / HAT-CN (5 nm) / TAPC (40 nm) / TCTA (10 nm) / TCTA:DPEPO:Cu6 (20 nm) / DPEPO (10 nm) / TPBi (40 nm) / LiF (1.2 nm) / Al (100 nm). [Figure 23A]FIG. 23A is a line graph showing the EL spectrum and performance characteristics of a vapor-deposited hyper-fluorescence OLED (containing Cu6 and ν-DABNA in mCBP). Device structure: ITO / HAT-CN(10 nm) / BPBPA(120 nm) / mCBP(10 nm) / mCBP:Cu6:ν-DABNA(20 nm) / SF3-TRz(5 nm) / SF3-TRz:Liq(1:1,25 nm) / Liq(2 nm) / Al(100 nm). [Figure 23B] FIG. 23B is a line graph showing the EL spectrum and performance characteristics of a deposition-based hyperfluorescent OLED (containing Cu6 and ν-DABNA in mCBP). Device structure: ITO / HAT-CN(10 nm) / BPBPA(120 nm) / mCBP(10 nm) / mCBP:Cu6:ν-DABNA(20 nm) / SF3-TRz(5 nm) / SF3-TRz:Liq(1:1,25 nm) / Liq(2 nm) / Al(100 nm). [Figure 23C] FIG. 23C is a line graph showing the EL spectrum and performance characteristics of a deposition-based hyperfluorescent OLED (containing Cu6 and ν-DABNA in mCBP). Device structure: ITO / HAT-CN(10 nm) / BPBPA(120 nm) / mCBP(10 nm) / mCBP:Cu6:ν-DABNA(20 nm) / SF3-TRz(5 nm) / SF3-TRz:Liq(1:1,25 nm) / Liq(2 nm) / Al(100 nm). [Figure 23D]FIG. 23D is a line graph showing the EL spectrum and performance characteristics of a deposition-based hyperfluorescent OLED (containing Cu6 and ν-DABNA in mCBP). Device structure: ITO / HAT-CN(10 nm) / BPBPA(120 nm) / mCBP(10 nm) / mCBP:Cu6:ν-DABNA(20 nm) / SF3-TRz(5 nm) / SF3-TRz:Liq(1:1,25 nm) / Liq(2 nm) / Al(100 nm). [Figure 24A] FIG. 24A is a line graph (or line graph) showing the EL spectrum and performance characteristics of Cu7(DMIC-Cz:DMIC-Trz(co-host (doping concentration 2-6 wt / wt%). Device structure: ITO / HAT-CN(10 nm) / BPBOA(80 nm) / FSF4A(5 nm) / DMIC-Cz:DMIC-Trz:Cu7(30 nm) / ANT-Biz(5 nm) / ANT-Biz:Liq(25 nm) / Liq(2 nm) / Al(100 nm). [Figure 24B] FIG. 24B is a line graph (or line graph) showing the EL spectrum and performance characteristics of Cu7(DMIC-Cz:DMIC-Trz(co-host (doping concentration 2-6 wt / wt%). Device structure: ITO / HAT-CN(10 nm) / BPBOA(80 nm) / FSF4A(5 nm) / DMIC-Cz:DMIC-Trz:Cu7(30 nm) / ANT-Biz(5 nm) / ANT-Biz:Liq(25 nm) / Liq(2 nm) / Al(100 nm). [Figure 24C] FIG. 24C is a line graph (or line graph) showing the EL spectrum and performance characteristics of Cu7(DMIC-Cz:DMIC-Trz(co-host (doping concentration 2-6 wt / wt%). Device structure: ITO / HAT-CN(10 nm) / BPBOA(80 nm) / FSF4A(5 nm) / DMIC-Cz:DMIC-Trz:Cu7(30 nm) / ANT-Biz(5 nm) / ANT-Biz:Liq(25 nm) / Liq(2 nm) / Al(100 nm). [Figure 24D] FIG. 24D is a line graph (or line graph) showing the EL spectrum and performance characteristics of Cu7(DMIC-Cz:DMIC-Trz(co-host (doping concentration 2-6 wt / wt%). Device structure: ITO / HAT-CN(10 nm) / BPBOA(80 nm) / FSF4A(5 nm) / DMIC-Cz:DMIC-Trz:Cu7(30 nm) / ANT-Biz(5 nm) / ANT-Biz:Liq(25 nm) / Liq(2 nm) / Al(100 nm). [Figure 25A] FIG. 25A is a line graph showing the EL spectrum and performance characteristics of a vapor-deposited hyper-fluorescence OLED (containing Cu7 and MR-R in RH). Device structure: ITO / HAT-CN(10 nm) / HT(40 nm) / EB(5 nm) / Cu7:MR-R:RH(40 nm) / HB(5 nm) / ZADN:Liq(35:65)(35 nm) / Liq(2 nm) / Al(100 nm). [Figure 25B] FIG. 25B is a line graph showing the EL spectrum and performance characteristics of a deposition-based hyperfluorescent OLED (containing Cu7 and MR-R in RH). Device structure: ITO / HAT-CN(10 nm) / HT(40 nm) / EB(5 nm) / Cu7:MR-R:RH(40 nm) / HB(5 nm) / ZADN:Liq(35:65)(35 nm) / Liq(2 nm) / Al(100 nm). [Figure 25C] FIG. 25C is a line graph showing the EL spectrum and performance characteristics of a deposition-based hyperfluorescent OLED (containing Cu7 and MR-R in RH). Device structure: ITO / HAT-CN(10 nm) / HT(40 nm) / EB(5 nm) / Cu7:MR-R:RH(40 nm) / HB(5 nm) / ZADN:Liq(35:65)(35 nm) / Liq(2 nm) / Al(100 nm). [Figure 25D] FIG. 25D is a line graph showing the EL spectrum and performance characteristics of a deposition-based hyperfluorescent OLED (containing Cu7 and MR-R in RH). Device structure: ITO / HAT-CN(10 nm) / HT(40 nm) / EB(5 nm) / Cu7:MR-R:RH(40 nm) / HB(5 nm) / ZADN:Liq(35:65)(35 nm) / Liq(2 nm) / Al(100 nm). [Figure 26A] FIG. 26A is a line graph showing the EL spectrum and performance characteristics of a vapor-deposited hyper-fluorescence OLED (containing Au3 and BN-2 in mCBP). Device structure: ITO / HAT-CN(5 nm) / TAPC(40 nm) / mCBP(10 nm) / Au3:BN-2:mCBP(20 nm) / PPF(10 nm) / TmPyPb(40 nm) / LiF(1.2 nm) / Al(100 nm). [Figure 26B] FIG. 26B is a line graph showing the EL spectrum and performance characteristics of a deposition-based hyperfluorescent OLED (containing Au3 and BN-2 in mCBP). Device structure: ITO / HAT-CN(5 nm) / TAPC(40 nm) / mCBP(10 nm) / Au3:BN-2:mCBP(20 nm) / PPF(10 nm) / TmPyPb(40 nm) / LiF(1.2 nm) / Al(100 nm). [Figure 26C] FIG. 26C is a line graph showing the EL spectrum and performance characteristics of a deposition-based hyperfluorescent OLED (containing Au3 and BN-2 in mCBP). Device structure: ITO / HAT-CN(5 nm) / TAPC(40 nm) / mCBP(10 nm) / Au3:BN-2:mCBP(20 nm) / PPF(10 nm) / TmPyPb(40 nm) / LiF(1.2 nm) / Al(100 nm). [Figure 26D] FIG. 26D is a line graph showing the EL spectrum and performance characteristics of a deposition-based hyperfluorescent OLED (containing Au3 and BN-2 in mCBP). Device structure: ITO / HAT-CN(5 nm) / TAPC(40 nm) / mCBP(10 nm) / Au3:BN-2:mCBP(20 nm) / PPF(10 nm) / TmPyPb(40 nm) / LiF(1.2 nm) / Al(100 nm). [Figure 27A] Figure 27A is a line graph (or line graph) showing the EL spectrum and performance characteristics of Au5 (mCBP:CzSiTrz (co-host)) (doping concentration 2-8 wt / wt%). Device structure: ITO / HAT-CN (10 nm) / FSFA (120 nm) / mCBP (10 nm) / mCBP:CzSiTrz:Au5 (30 nm) / SF3-Trz (5 nm) / SF3-Trz:Liq (25 nm) / Liq (2 nm) / Al (100 nm). [Figure 27B] Figure 27B is a line graph (or line graph) showing the EL spectrum and performance characteristics of Au5 (mCBP:CzSiTrz (co-host)) (doping concentration 2-8 wt / wt%). Device structure: ITO / HAT-CN (10 nm) / FSFA (120 nm) / mCBP (10 nm) / mCBP:CzSiTrz:Au5 (30 nm) / SF3-Trz (5 nm) / SF3-Trz:Liq (25 nm) / Liq (2 nm) / Al (100 nm). [Figure 27C] Figure 27C is a line graph (or line graph) showing the EL spectrum and performance characteristics of Au5 (mCBP:CzSiTrz (co-host)) (doping concentration 2-8 wt / wt%). Device structure: ITO / HAT-CN (10 nm) / FSFA (120 nm) / mCBP (10 nm) / mCBP:CzSiTrz:Au5 (30 nm) / SF3-Trz (5 nm) / SF3-Trz:Liq (25 nm) / Liq (2 nm) / Al (100 nm). [Figure 27D]Figure 27D is a line graph (or line graph) showing the EL spectrum and performance characteristics of Au5 (mCBP:CzSiTrz (co-host)) (doping concentration 2-8 wt / wt%). Device structure: ITO / HAT-CN (10 nm) / FSFA (120 nm) / mCBP (10 nm) / mCBP:CzSiTrz:Au5 (30 nm) / SF3-Trz (5 nm) / SF3-Trz:Liq (25 nm) / Liq (2 nm) / Al (100 nm). [Figure 28] Figure 28 is a line graph showing the emission spectrum of Au10 (in MCP film). [Figure 29] Figure 29 is a line graph showing the emission spectrum of Au11 (in MCP film). DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] Detailed Description of the Invention (I) Definition "Alkyl" includes straight-chain and branched-chain alkyl groups, as well as cycloalkyl groups (wherein the alkyl group has a cyclic structure). Preferred alkyl groups are those containing 1 to 18 carbon atoms, including methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, and other similar compounds. Additionally, the alkyl group may be substituted, as appropriate, with one or more substituents, such as halogen, deuterium, formaldehyde, cyano, alkylalkynyl, substituted alkylalkynyl, arylalkynyl, substituted arylalkynyl, heteroarylalkynyl, substituted heteroarylalkynyl, fused polycyclic (groups), substituted fused polycyclic (groups), aryl, alkyl, heteroaryl, nitro, trifluoromethane, cyano, aryl ether, alkyl ether, heteroaryl ether, diarylamine, dialkylamine, diheteroarylamine, diarylborane, triarylsilane, trialkylsilane, alkenyl, alkylaryl, cycloalkyl, haloformyl, hydroxyl, aldehyde, carboxamide, amine, amino, alkoxy, azo, benzyl, carbonate, Selected from ester, carboxylate, carboxyl, ketamine (or ketoamine), isocyanate, isocyanide, isothiocyanate, nitrile, nitro, nitroso, phosphine, phosphate, phosphono, pyridyl, sulfonyl, sulfo, sulfinyl, sulfhydryl, halo, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclic (groups) and derivatives thereof.

[0013] It will be understood by those skilled in the art that the sites (or moieties) substituted on the hydrocarbon chain can themselves be substituted, if appropriate. For example, substituents of substituted alkyls can include halogen, hydroxy, nitro, thiol, amino, azide, imino, amido, phosphoryl (including phosphonates and phosphinates), sulfonyl (including sulfates, sulfonamides, sulfamoyl and sulfonates), and silyl groups, as well as ethers, alkylthios, carbonyls (including ketones, aldehydes, carboxylates and esters), haloalkyls, -CN, and the like. Cycloalkyls may be substituted in a similar fashion.

[0014] "Substituted" as used herein means all possible substitutions in the compounds or functional groups described herein. 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), and in a linear, branched, or cyclic structural format. Representative substituents include alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, phenyl, substituted phenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halo, hydroxyl, alkoxy, substituted alkoxy, phenoxy, substituted phenoxy, aroxy, substituted aroxy, alkylthio, substituted alkylthio, phenylthio, substituted phenylthio, arylthio, substituted arylthio, cyano, isocyano, substituted isocyano, oxo (=O), carbonyl, substituted carbonyl, carboxyl, substituted carboxyl, amino, substituted amino, amido, substituted amido, sulfonyl, substituted sulfonyl, sulfonic acid, phosphoryl, substituted phosphoryl, phosphonyl, substituted phosphonyl, polyaryl, substituted polyaryl, cyclic (groups) (e.g., C3-C 20 cyclic (group)), substituted cyclic (group) (e.g., substituted C3-C 20cyclic (groups), heterocyclic (groups), substituted heterocyclic (groups), amino acids, poly(lactic-co-glycolic acid), peptide, polypeptide, deuterium, unsubstituted alkylalkynyl, substituted alkylalkynyl, unsubstituted arylalkynyl, substituted arylalkynyl, unsubstituted heteroarylalkynyl, substituted heteroarylalkynyl, trihaloalkyl (trifluoromethyl), unsubstituted heteroarylether, substituted heteroarylether, unsubstituted diarylamino, substituted diarylamino, unsubstituted dialkylamino, substituted dialkylamino, unsubstituted diheteroarylamino, substituted diheteroarylamino, unsubstituted diarylboraneyl, substituted diarylboranyl, unsubstituted triarylsilyl, substituted triarylsilyl, unsubstituted trialkylsilyl, substituted trialkylsilyl, azo, carbonate ester, ketamine, nitro, nitroso, phosphino, pyridyl, NRR',SR, C(O)R,The groups COOR, C(O)NR, SOR and BRR', where R and R' are independently selected from the following: hydrogen, deuterium, formaldehyde, cyano, alkylalkynyl, substituted alkylalkynyl, arylalkynyl, substituted arylalkynyl, heteroarylalkynyl, substituted heteroarylalkynyl, fused polycyclic (groups), substituted fused polycyclic (groups), aryl, alkyl, heteroaryl, nitro, trifluoromethane, cyano, aryl ether, alkyl ether, heteroaryl ether, diarylamine, dialkylamine, diheteroarylamine, diaryl borane, triarylsilane, trialkylsilane, alkenyl, alkylaryl, cycloalkyl, haloformyl, hydroxyl, aldehyde, carboxamide, amine, amino, alkoxy, azo, benzyl, carbonate ester, carboxylate, carboxyl, ketamine (or ketoamine), isocyanate, isocyanide, isothiocyanate, nitrile, nitro, nitroso, phosphine, phosphate, phosphono, pyridyl, sulfonyl, sulfo, sulfinyl, sulfhydryl, halo, aryl, substituted aryl, heteroaryl, substituted heteroaryl and heterocyclic (or cyclic) groups. Such alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, phenyl, substituted phenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halo, hydroxyl, alkoxy, substituted alkoxy, phenoxy, substituted phenoxy, aroxy, substituted aroxy, alkylthio, substituted alkylthio, phenylthio, substituted phenylthio, arylthio, substituted arylthio, cyano, isocyano, substituted isocyano, carbonyl, substituted carbonyl, carboxyl, substituted carboxyl, amino, substituted amino, amido, substituted amido, sulfonyl, substituted sulfonyl, sulfonic acid, phosphoryl, substituted phosphoryl, phosphonyl, substituted phosphonyl, polyaryl, substituted polyaryl, cyclic (group) (e.g., C3-C 20cyclic (group)), substituted cyclic (group) (e.g., substituted C3-C 20 cyclic (groups), heterocyclic (groups), substituted heterocyclic (groups), amino acids, poly(lactic-co-glycolic acid), peptides, polypeptides, deuterium, unsubstituted alkyl alkynyl, substituted alkyl alkynyl, unsubstituted aryl alkynyl, substituted aryl alkynyl, unsubstituted heteroaryl alkynyl, substituted heteroaryl alkynyl, trihaloalkyl (trifluoromethyl), unsubstituted heteroaryl ether, substituted heteroaryl ether, unsubstituted diarylamino, substituted diarylamino, unsubstituted dialkylamino, substituted dialkylamino, unsubstituted diheteroarylamino, substituted diheteroarylamino, unsubstituted diarylboraneyl, substituted diarylboranyl, unsubstituted triarylsilyl, substituted triarylsilyl, unsubstituted trialkylsilyl, substituted trialkylsilyl, azo, carbonate The ester, ketamine, nitro, nitroso, phosphide, phosphino and pyridyl groups may be further substituted.

[0015] The term "heteroatom" as used in this disclosure includes, but is not limited to, S, O, N, P, Se, Te, As, Sb, Bi, B, Si, Ge, Sn, and Pb. The heteroatoms (e.g., nitrogen) may have hydrogen substituents and / or any possible substituents of organic compounds described herein which satisfy the valences (or valences or valence) of the heteroatoms. It is understood that "substitution" or "substituted" includes the implicit understanding, provided that such substitution is subject to the possible valences of the atom being substituted and the substitution. It is also understood that such substitution results in a stable compound (i.e., a compound that does not spontaneously undergo transformation, such as by rearrangement, cyclization, elimination, etc.). The term "alkenyl," as used in this disclosure, refers to a hydrocarbon group, e.g., having 2 to 24 carbon atoms and having a structural formula containing at least one carbon-carbon double bond. Asymmetric structures (eg, (AB)C=C(CD)) are intended to include both the E and Z isomers (or isomers). This may be assumed in the present disclosure in structural formulas where an unsymmetrical alkene is present, or this may be explicitly indicated by the bond symbol C.

[0016] The term "alkynyl group," as used in this disclosure, refers to a hydrocarbon group, e.g., having 2 to 24 carbon atoms and having a structural formula that includes at least one carbon-carbon triple bond.

[0017] The term "aryl" as used in this disclosure refers to any C5-C 26 The ring system may be a carbon-based (or carbon-based) aromatic group, a fused aromatic system, a fused heterocyclic system, or a biaromatic ring system. In a broad sense, "aryl" as used herein includes 5-, 6-, 7-, 8-, 9-, 10-, 14-, 18-, and 24-membered monocyclic aromatic groups, including, but not limited to, benzene, naphthalene, anthracene, phenanthrene, chrysene, pyrene, corannulene, coronene, and the like. "Aryl" also includes polycyclic ring systems, having two or more cyclic rings (or cyclic rings) where two or more carbons are common to two adjacent rings (i.e., "fused rings"), where at least one ring is aromatic. For example, the other cyclic ring (or rings) can be cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, and / or heterocycle (or heterocycle or heterocycle). Aryl groups may be substituted with one or more groups, including but not limited to alkyl, alkynyl, alkenyl, aryl, halide, nitro, amino, ester, ketone, aldehyde, hydroxy, carboxylic acid, or alkoxy.

[0018] The term "substituted aryl" means an aryl group in which one or more hydrogen atoms in one or more aromatic rings (or 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, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl (e.g., -CF3, -CH2-CF3, -CCl3), -CN, aryl, heteroaryl, and combinations thereof.

[0019] The terms "heterocycle", "heterocyclic" and "heterocyclyl" are used interchangeably and refer to a cyclic group or radical bonded through a carbon or nitrogen atom of the ring, which may be in a monocyclic, bicyclic or tricyclic ring, containing 3 to 14 ring atoms, preferably 5 to 6 ring atoms, and consisting of carbon and 1 to 4 heteroatoms. The heteroatoms are selected from the group consisting of non-peroxide oxygen, sulfur and N (Y), respectively, where Y is absent or absent or selected from H, O, C1-C2, C3-C4, C4-C5, C6-C7, C8-C9, C10-C11, C12-C13, C14-C15, C16-C17, C18-C19, C19-C20, C19-C21, C19-C22, C18-C23, C19-C31, C19-C24, C19-C25, C20-C32, C20-C33, C20-C34, C20-C35, C20-C36, C20-C37, C20-C38, C20-C39, C21-C38, C22-C39, C23-C44, C24-C39, C25-C38, C25-C39, C26-C31, C27-C31, C28-C32, C29-C33, C29-C34, C29-C35, C31-C32, C29-C34, C29-C35, C31-C32, C29-C33, C31-C34, C29-C35, C31-C32, C31-C33, C31-C34, C31-C35, C31 10Optionally, 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. Examples of heterocycles (or heterocycles or heterocycles) include, but are not limited to, 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 groups or heterocyclic groups) may be optionally substituted with one or more substituents as defined above for alkyl and aryl.

[0020] The term "heteroaryl" refers to any of the C5 to C6 26 By this is meant a 1-membered aromatic, fused aromatic, biaromatic ring system or a combination thereof. wherein one or more carbon atoms in 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. In a broad sense, "heteroaryl," as used herein, includes 5-, 6-, 7-, 8-, 9-, 10-, 14-, 18-, and 24-membered monocyclic aromatic groups which may contain 1 to 4 heteroatoms, such as, for example, pyrrole, furan, thiophene, imidazole, oxazole, thiazole, triazole, tetrazole, pyrazole, pyridine, pyrazine, pyridazine, and pyrimidine. Heteroaryl groups may also be referred to as "aryl heterocycles" or "heteroaromatics". "Heteroaryl" also includes polycyclic ring systems having two or more rings in which two or more carbons are common to two adjacent rings (i.e., "fused rings"), where at least one ring is a heteroaromatic ring. For example, the other cyclic ring(s) can be cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heterocycle, or combinations thereof. 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. For "substituted heteroaryl," one or more rings may be substituted as defined (or specified) below.

[0021] The term "substituted heteroaryl" means a heteroaryl group in which one or more hydrogen atoms in one or more of the heteroaromatic rings is 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, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl (e.g., -CF3, -CH2-CF3, -CCl3), -CN, aryl, heteroaryl, and combinations thereof.

[0022] The term "substituted alkenyl" means an alkenyl moiety (or portion) having one or more substituents replacing one or more hydrogen atoms on one or more carbons of the hydrocarbon backbone. 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, phosphoryl, phosphate, phosphonate, phosphinate, amino (or quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof.

[0023] The term "substituted alkynyl" means an alkynyl moiety (or moiety) having one or more substituents replacing one or more hydrogen atoms on one or more carbons of the hydrocarbon backbone. 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, phosphoryl, phosphate, phosphonate, phosphinate, amino (or quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof.

[0024] The term "cycloalkyl," as used in this disclosure, refers to a non-aromatic carbon-based ring composed of at least three carbon atoms. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. The term "heterocycloalkyl group" refers to a cycloalkyl group, as defined above, in which at least one carbon atom of the ring is replaced with a heteroatom, such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus.

[0025] The term "aralkyl," as used in this disclosure, refers to an aryl group having an alkyl, alkynyl, or alkenyl group (as defined above) attached to its aromatic radical. An example of an aralkyl group is the benzyl group.

[0026] The term "carbonyl," as used in this disclosure, is art-recognized and includes a moiety that may be represented in the general formula: [ka] In the formula, X represents 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 cycloalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, -(CH2) m -R'', or a pharma- ceutically acceptable salt, where R' represents hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; or -(CH) m -R" (R" represents a hydroxy group, a substituted or unsubstituted carbonyl group, an aryl, a cycloalkyl ring, a cycloalkenyl ring, a heterocycle or a polycycle); m is zero (0) or an integer ranging from 1 to 8. When X is oxygen and R is as defined above, such a moiety is also referred to as a carboxyl group. Where X is an oxygen and R is a hydrogen, the above formula represents a "carboxylic acid." Where X is an oxygen and R' is hydrogen, the above formula represents a "formate." Where X is an oxygen and R or R' is not hydrogen, the above formula represents an "ester." In general, where the oxygen atom of the above formula is replaced by a sulfur atom, the above formula represents a "thiocarbonyl" group. Where X is a sulfur and R or R' is not hydrogen, the above formula represents a "thioester." Where X is a sulfur and R is hydrogen, the above formula represents a "thiocarboxylic acid." Where X is a sulfur and R' is hydrogen, the above 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."

[0027] The term "substituted carbonyl" means a carbonyl (as defined above) in which one or more hydrogen atoms are independently replaced, where such hydrogen atoms are selected from the group consisting of R, R', and the following moieties: [ka] is in the bonding group. 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, phosphoryl, phosphate, phosphonate, phosphinate, amino (or quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof.

[0028] The term "carboxyl" refers to a group having the following formula: [ka] As defined (or defined) above, and more specifically, the formula: -R iv COOH [In the formula, R iv is alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, alkylaryl, arylalkyl, aryl, or heteroaryl. It is defined (or prescribed) by: In a preferred embodiment, the straight or branched alkyl, alkenyl and alkynyl are alkyl, alkenyl, or alkynyl groups having a cyclic or cyclic structure in their backbone (e.g., C1-C 30 Straight chain alkyl, C3-C 30 Branched chain alkyl, C2-C 30 Straight chain alkenyl and alkynyl, C3-C 30 branched chain alkenyl and alkynyl) have up to 30, preferably up to 20, more preferably up to 15, and most preferably up to 10 carbon atoms. Likewise, preferred cycloalkyls, heterocyclyls, aryls, and heteroaryls have from 3-10 carbon atoms in their ring structure, and more preferably have 5, 6 or 7 carbons in the ring structure.

[0029] The term "substituted carboxyl" refers to a carboxyl as defined above, where R iv In the formula (I), one or more hydrogen atoms have been replaced. 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, phosphoryl, phosphate, phosphonate, phosphinate, amino (or quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof.

[0030] The term "phenoxy" as understood refers to a group of the formula: -OR v [In the formula, R v means a compound of formula (i.e., -O-C6H5). Those skilled in the art will appreciate that phenoxy is a member of the aroxy genus.

[0031] The term "substituted phenoxy" means a phenoxy group (as defined 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, phosphoryl, phosphate, phosphonate, phosphinate, amino (or quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof.

[0032] 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 (or specified) in this disclosure.

[0033] The terms "substituted aroxy" and "substituted aryloxy" are used interchangeably in this disclosure and 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 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), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof.

[0034] The term "alkylthio" means an alkyl group, as defined above, having a sulfur group (or radical) attached thereto. The "alkylthio" moiety (or portion) is represented by -S-alkyl. Representative alkylthio groups include methylthio, ethylthio, and the like. The term "alkylthio" also includes cycloalkyl groups that contain a sulfur group (or radical) attached thereto.

[0035] The term "substituted alkylthio" means alkylthio groups having one or more substituents replacing one or more hydrogen atoms on one or more carbon atoms of the alkylthio backbone. 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, phosphoryl, phosphate, phosphonate, phosphinate, amino (or quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof.

[0036] The term "phenylthio" is art-recognized to mean -S-C6H5 (i.e., a phenyl group bonded to a sulfur atom).

[0037] The term "substituted phenylthio" means a phenylthio group (as defined above) having one or more substituents replacing a hydrogen 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, phosphoryl, phosphate, phosphonate, phosphinate, amino (or quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof.

[0038] "Arylthio" refers to the group -S-aryl or -S-heteroaryl, where aryl and heteroaryl are as defined in this disclosure.

[0039] The term "substituted arylthio" refers to an -S-aryl or -S-heteroaryl having one or more substituents replacing a hydrogen atom on one or more ring atoms of the aryl and heteroaryl ring (as defined (or prescribed) in this disclosure). 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, phosphoryl, phosphate, phosphonate, phosphinate, amino (or quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof.

[0040] The terms "amide" or "amido" are used interchangeably and refer to both "unsubstituted amido" and "substituted amido" and are represented by the general formula: [ka] wherein E is absent (or non-existent or 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 heterocyclyl. wherein, independent of E, R and R' are each independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbonyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, -(CH2) m -R'''. Alternatively, R and R', together with the N atom to which they are attached, complete a heterocycle (or heterocyclic ring or heterocycle), such heterocycles having from 3 to 14 atoms in the ring structure. R''' represents a hydroxy group, a substituted or unsubstituted carbonyl group, an aryl, a cycloalkyl ring, a cycloalkenyl ring, a heterocycle (or heterocycle or heterocyclyl) or a polycycle (or polycycle). m is zero (0) or an integer ranging from 1 to 8. In a preferred embodiment, only one of R and R' may be a carbonyl, e.g., R and R' together with the nitrogen do not form an imide. In a preferred embodiment, R and R' are each independently a hydrogen atom, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, or -(CH2) m When E is oxygen, a carbamate is formed (or generated). A carbamate cannot bond to another chemical species, for example, to form an oxygen-oxygen bond or other labile bond, as would be understood by one of skill in the art.

[0041] The term "sulfonyl" is represented by the formula: [ka] In the formula, E is not present (or is non-existent). Alternatively, E is alkyl, alkenyl, alkynyl, aralkyl, alkylaryl, cycloalkyl, aryl, heteroaryl, heterocyclyl. wherein, independently of E, R is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted amine, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, -(CH) m -R'''. Alternatively, E and R, together with the S atom to which they are attached, complete a heterocycle (or heterocycle or heterocycle) having from 3 to 14 atoms in the ring structure. R''' represents a hydroxy group, a substituted or unsubstituted carbonyl group, an aryl, a cycloalkyl ring, a cycloalkenyl ring, a heterocycle (or heterocycle or heterocycle) or a polycycle (or polycycle). m is zero (0) or an integer ranging from 1 to 8. In a preferred form, only one of E and R may be a substituted or unsubstituted amine, forming (or generating) a "sulfonamide" or "sulfonamido". The substituted or unsubstituted amines are as defined (or specified) above.

[0042] The term "substituted sulfonyl" refers to sulfonyl in which E, R, or both, are independently substituted. 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, phosphoryl, phosphate, phosphonate, phosphinate, amino (or quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof.

[0043] The term "sulfonic acid" means sulfonyl (as defined (or specified) above), R is hydroxyl, and E is absent (or absent or 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 or substituted or unsubstituted heteroaryl.

[0044] The term "sulfate" means sulfonyl (as defined above), E is absent (or absent or 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, for example to form an oxygen-oxygen bond or other labile bond, as would be understood by one of ordinary skill in the art.

[0045] The term "sulfonate" refers to sulfonyl (as defined above), E is oxygen, alkoxy, aroxy, substituted alkoxy, or substituted aroxy (as defined above), and R is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted amine, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, -(CH) m -R''', where R''' represents a hydroxy group (or hydroxyl group), a substituted or unsubstituted carbonyl group, an aryl, a cycloalkyl ring, a cycloalkenyl ring, a heterocycle (or heterocycle or heterocycle) or a polycycle (or polycycle), and m is zero (0) or an integer ranging from 1 to 8. When E is oxygen, the sulfonate cannot be bonded to another chemical species, for example to form an oxygen-oxygen bond or other labile bond, as would be understood by one of ordinary skill in the art.

[0046] The term "sulfamoyl" refers to a sulfonamide or sulfonamide represented by the following formula: [ka] wherein E is absent (or non-existent or absent), or E is substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aralkyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl. wherein, independent of E, R and R' are each independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbonyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, -(CH2) m -R'''. Alternatively, R and R', together with the N atom to which they are attached, complete a heterocycle (or heterocyclic ring or heterocycle), such heterocycles having from 3 to 14 atoms in the ring structure. R''' represents a hydroxy group, a substituted or unsubstituted carbonyl group, an aryl, a cycloalkyl ring, a cycloalkenyl ring, a heterocycle (or heterocycle or heterocycle) or a polycycle (or polycycle). m is zero (0) or an integer ranging from 1 to 8. In a preferred embodiment, only one of R and R' may be a carbonyl, e.g., R and R' together with the nitrogen do not form an imide.

[0047] The term "phosphonyl" is represented by the formula: [ka] wherein E is absent (or non-existent or absent), or E is substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aralkyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl. 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 cycloalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, -(CH2) m -R'''. Alternatively, R and R', together with the P atom to which they are attached, complete a heterocycle (or heterocyclic ring or heterocycle), such heterocycles having from 3 to 14 atoms in the ring structure. R''' represents a hydroxy group, a substituted or unsubstituted carbonyl group, an aryl, a cycloalkyl ring, a cycloalkenyl ring, a heterocycle (or heterocycle or heterocycle) or a polycycle (or polycycle). m is zero (0) or an integer ranging from 1 to 8.

[0048] The term "substituted phosphonyl" refers to a phosphonyl having E, R vi and R vii are independently substituted. 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, phosphoryl, phosphate, phosphonate, phosphinate, amino (or quaternized amino), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof.

[0049] The term "phosphoryl" defines (or specifies) phosphonyl, in which E is absent (or non-existent), oxygen, alkoxy, aroxy, substituted alkoxy, or substituted aroxy (as defined (or specified) above). Independent of E, R vi and R vii is independently hydroxyl, alkoxy, aroxy, substituted alkoxy, or substituted aroxy, as defined (or specified) above. When E is oxygen, the phosphoryl cannot be bonded to another chemical species, for example to form an oxygen-oxygen bond or other labile bond, as would be understood by one of 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 (or 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 term "polyaryl" refers to a chemical moiety (or moiety) that contains two or more aryl, heteroaryl, and combinations thereof. Aryl, heteroaryl and combinations thereof may be fused or connected (or connected or bonded or linked) via single bonds, ethers, esters, carbonyls, amides, sulfonyls, sulfonamides, alkyls, azos and combinations thereof. When more than one heteroaryl is included, the chemical moiety (or moiety) may be referred to as a "polyheteroaryl."

[0051] The term "substituted polyaryl" refers to a polyaryl in which one or more aryl, heteroaryl groups are substituted with one or more substituents. 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), amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof. When more than one heteroaryl is included, such a chemical moiety (or moiety) may be referred to as a "substituted polyheteroaryl."

[0052] The term "cyclic" means substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted cycloalkynyl, substituted or unsubstituted cycloalkynyl, substituted or unsubstituted heterocyclyl, preferably having from 3 to 20 carbon atoms, where geometric constraints permit. Such cyclic structures (or ring structures) may be formed (or produced) from a single ring system or a fused ring system. Substituted cycloalkyl, substituted cycloalkenyl, substituted cycloalkynyl and substituted heterocyclyl are substituted as defined (or specified) above for alkyl, alkenyl, alkynyl and heterocyclyl, respectively.

[0053] (II) Composition Disclosed are two-coordinated d10 metal carbene complexes that include imidazopyrazine ligands (e.g., pyrazine-fused N-heterocyclic carbene (NHC) ligands), imidazopyridine ligands (e.g., pyridine-fused NHC ligands), or pyrrolopyrazine ligands (e.g., pyrazine-fused NHC ligands). The radiative properties of this compound can be tuned (or controlled) by TADF. Preferably, the d10 metal carbene complex comprises a d10 metal (e.g., Cu(I), Ag(I) or Au(I)) in a +1-oxidation state, a pyrazine-fused NHC ligand and a carbazole ligand. Preferred pyrazine-fused NHC ligands (or pyrazine-fused NHC ligands) or pyridine-fused N-heterocyclic carbene ligands (or pyridine-fused N-heterocyclic carbene ligands) comprise a 2,6-diisopropylphenyl group, which is covalently bonded to a nitrogen atom at the imidazole site (or moiety) of the pyrazine-fused NHC ligands (or pyrazine-fused NHC ligands). The compounds of the present disclosure include (i) It is easy to manufacture on a large scale. (ii) It is cheaper to manufacture because it uses a metal (copper) that is abundant on Earth. (iii) Exhibiting tunable color emission properties (e.g., from blue-green to orange-red). (iv) The OLEDs are both sublimable and solution processable for fabrication. (v) exhibiting improved OLED luminance (or brightness) and efficiency (or efficiency) compared to existing emitters; and / or (vi) It shows improved device stability compared to conventional (or reported) d10Cu / Ag / Au emitters.

[0054] The compounds of the present disclosure have the structure of Formula I: [ka] Formula I The compound has an overall neutral, negative or positive charge, M is copper, silver or gold, the oxidation state of which is 0, +1, +2 or +3, preferably +1; P' has the structure of formula I' below: [ka] Formula I' D is carbon; T, J and W are independently carbon or nitrogen, at least one of T, J and W is nitrogen, and when T is carbon, J is nitrogen, or when T is nitrogen, J is carbon, and T, J and W are bonded to one or no hydrogen atoms according to valency; X and Y are independently carbon or nitrogen, at least one of X and Y is nitrogen, and X and Y are bonded to one or no hydrogen atoms according to valency; R1 and R2 are independently selected from 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 C3-C 20 Cycloalkyl, unsubstituted C3-C 20 Cycloalkyl, Substituted C2-C 20 Heterocyclyl, unsubstituted C2-C 20 Heterocyclyl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 Cycloalkenyl, substituted C3-C 20 Cycloalkynyl or unsubstituted C3-C 20cycloalkynyl, or R1, J, D and R2 taken together form (or generate) an unsubstituted aryl, substituted aryl, unsubstituted heteroaryl or substituted heteroaryl; R3 and R4 are independently selected from hydrogen, 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 C3-C 20 Cycloalkyl, unsubstituted C3-C 20 Cycloalkyl, Substituted C2-C 20 Heterocyclyl, unsubstituted C2-C 20 Heterocyclyl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 Cycloalkenyl, substituted C3-C 20 Cycloalkynyl or unsubstituted C3-C 20 is cycloalkynyl, R3' and R4' 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 C3-C 20 Cycloalkyl, unsubstituted C3-C 20 Cycloalkyl, Substituted C2-C 20 Heterocyclyl, unsubstituted C2-C 20 Heterocyclyl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 Cycloalkenyl, substituted C3-C 20 Cycloalkynyl or unsubstituted C3-C 20 is cycloalkynyl, Z is a substituted heteroaryl, an unsubstituted heteroaryl, a substituted polyheteroaryl, an unsubstituted polyheteroaryl, a substituted polyheterocyclyl, an unsubstituted polyheterocyclyl, a substituted or unsubstituted heterocyclyl, or -NR a R b where R a and R b are independently hydrogen, substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C-C 20 Cycloalkyl, unsubstituted C3-C 20cycloalkyl, substituted heterocyclyl, unsubstituted heterocyclyl, substituted alkyl or unsubstituted alkyl; (i) R3 and R4 are not both 3,5-dialkyl substituted aryl; (ii) R3 and R4 are not both 3,5-dialkyl substituted phenyl; (iii) R3 and R4 are not both 3,5-dimethylphenyl; (iv) R3 and R4 are not both 3,5-dimethylphenyl when M is Cu or Au; or (v) The compound is [ka] or [ka] isn't it.

[0055] In some embodiments, the compound is as described above for formula I, except that the compound has the structure of formula II: [ka] Formula II [In the formula, CY1 and CY2 are independently selected from substituted aryl, unsubstituted aryl, substituted polyaryl, unsubstituted polyaryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C3-C 20 Cycloalkyl, unsubstituted C3-C 20 Cycloalkyl, Substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 Cycloalkenyl, substituted C3-C 20 Cycloalkynyl or unsubstituted C3-C 20 cycloalkynyl] has. In some embodiments, CY1 and CY2 are independently substituted aryl, unsubstituted aryl, substituted polyaryl, or unsubstituted polyaryl. In some embodiments, CY1 and CY2 are substituted aryl.

[0056] In some embodiments, the compound is as described above for Formula I or Formula II, except that R3' and R4' are absent.

[0057] In some embodiments, the compound is as described above for Formula I or Formula II, except that the compound has the structure of Formula III: [ka] Formula III [In the formula, R5 and R6 are independently substituted or unsubstituted alkyl; n1 and n2 are independently an integer from 0 to 5, 1 to 5, 2 to 5 (e.g., 2); or an integer from 3 to 5 (e.g., 3). has.

[0058] In some embodiments, the compound is as described above for any of Formulas I-III, except that the compound has the structure of Formula IV: [ka] Formula IV [In the formula, n1 and n2 are independently an integer of 1 to 5, 2 to 5, or 3 to 5; L is absent, a single bond, a substituted alkyl, -(CH2) nx -, oxygen, sulfur, or NRx, where nx is an integer from 1 to 3 (e.g., 1, 2, or 3), and Rx is unsubstituted alkyl, substituted alkyl, unsubstituted aryl, or substituted aryl; CY3 and CY4 are independently unsubstituted aryl, substituted aryl, unsubstituted polyaryl, substituted polyaryl, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, unsubstituted C3-C 20 Cycloalkyl, Substituted C3-C 20 Cycloalkyl, 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. has.

[0059] In some embodiments, the compound is as described above for any of Formulas I-IV, except that the compound has the structure of Formula V: [ka] Formula V [In the formula, Each Ra is independently hydrogen, unsubstituted alkyl, or substituted alkyl; Each Rb is independently unsubstituted or substituted alkyl; L is absent, a single bond, a substituted alkyl, -(CH2) nx -, oxygen, sulfur, or NRx, where nx is an integer from 1 to 3 (e.g., 1, 2, or 3) and Rx is unsubstituted alkyl, substituted alkyl, unsubstituted aryl, or substituted aryl; Optionally, at least one of X and Y is nitrogen. has. In some embodiments, X and Y are nitrogen.

[0060] In some embodiments, the compound is as described above for any of Formulas I-V. Exceptions are as follows. (i) T is nitrogen, J is carbon and W is carbon, or (ii) T is nitrogen, J is carbon, and W is nitrogen, or (iii) T is carbon, J is nitrogen and W is carbon; or (iv) T is carbon, J is nitrogen, and W is nitrogen.

[0061] In some embodiments, the compound is as described above for formula V, except that Ra is hydrogen, unsubstituted alkyl or substituted alkyl, and Rb is unsubstituted alkyl or substituted alkyl.

[0062] In some embodiments, the compound is as described above for any of Formulas I-V, except that P' is: [ka] [In the formula, Ra is hydrogen, unsubstituted alkyl or substituted alkyl; Rb is unsubstituted alkyl or substituted alkyl. is selected from.

[0063] In some embodiments, the compound is as described above for any of Formulas I-V, where, in specific cases, Ra is hydrogen, methyl, iso-propyl, or -CH(C2H5)2, and Rb is methyl, iso-propyl, or -CH(C2H5)2.

[0064] In some embodiments, the compound is as described above for Formula IV or Formula V, except that CY3 and CY4 are independently unsubstituted aryl, substituted aryl, unsubstituted polyaryl, substituted polyaryl, unsubstituted heteroaryl, substituted heteroaryl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 cycloalkenyl, or fused combinations thereof. In some embodiments, CY3 and CY4 are independently selected from unsubstituted aryl, substituted aryl, unsubstituted heteroaryl, substituted heteroaryl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 cycloalkenyl, or fused combinations thereof.

[0065] In some embodiments, the compound is as described above for any of Formulas I-V, except that Z has the following structure: [ka] having X1, X2, X3, X4, X5, X6, X7 and X8 are independently carbon or nitrogen; R x1 , R x2 , R x3 , R x4 , R x5 , R x6 , R x7 and R x8 are independently hydrogen, halogen, cyano, unsubstituted alkyl, substituted alkyl, unsubstituted alkoxy, substituted alkoxy, unsubstituted aryl, substituted aryl, unsubstituted heteroaryl or substituted heteroaryl; R x1 , R x2 , R x3 , R x4 , R x5 , Rx6 , R x7 or R x8 When X1, X2, X3, X4, X5, X6, X7 or X8 corresponding to the above is nitrogen, or R x4 is a bond connecting to a substituent on L, or adjacent Rxn groups taken together with the atoms in the ring to which they are attached independently represent 5- or 6-membered substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 cycloalkenyl, or a condensed combination thereof (wherein adjacent R groups, n is a consecutive pair of integers from 1 to 4 or 5 to 8), R x1 , R x2 , R x3 , R x4 , R x5 , R x6 , R x7 or R x8 are not present (or non-existent or absent), L is absent, a single bond, a substituted alkyl, -(CH2), nx -, oxygen, sulfur, or NRx, where nx is an integer from 1 to 3 (e.g., 1, 2, or 3), and Rx is unsubstituted alkyl, substituted alkyl, unsubstituted aryl, or substituted aryl.

[0066] In some embodiments, the compound is as described above for any of Formulas I-V, except that Z has the following structure: [ka] having L' is substituted aryl, unsubstituted aryl, substituted heteroaryl or unsubstituted heteroaryl, preferably substituted aryl or unsubstituted aryl, preferably substituted phenyl or unsubstituted phenyl.

[0067] In some embodiments, the compound is as described above for any of Formulas I-V, except that Z has the following structure: [ka] having X1, X2, X3, X4, X5, X6, X7 and X8 are independently carbon or nitrogen; R x1 , R x2 , R x3 , R x4 , R x5 , R x6 , R x7 and R x8 are independently hydrogen, halogen, cyano, unsubstituted alkyl, substituted alkyl, unsubstituted alkoxy, substituted alkoxy, unsubstituted aryl, substituted aryl, unsubstituted heteroaryl or substituted heteroaryl; R x1 , R x2 , R x3 , R x4 , R x5 , R x6 , R x7 or R x8 When X1, X2, X3, X4, X5, X6, X7 or X8 corresponding to the formula (I) are nitrogen, or when adjacent Rxn groups taken together with the atoms in the ring to which they are attached independently represent 5- or 6-membered substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20cycloalkenyl, or a condensed combination thereof (wherein adjacent R groups, n is a consecutive pair of integers from 1 to 4 or 5 to 8), R x1 , R x2 , R x3 , R x4 , R x5 , R x6 , R x7 or R x8 are not present (or non-existent or absent), respectively.

[0068] In some embodiments, the compound is as described above for any of Formulas I-V. In particular cases, R x1 , R x2 , R x3 , R x4 , R x5 , R x6 , R x7 and R x8 is independently hydrogen, halogen, methyl, cyano, trifluoromethyl, tert-butyl, methoxy, phenyl, or pyridyl.

[0069] In some embodiments, the compound is as described above for any of Formulas I-V, except that the compound has the structure of Formula VI': [ka] Formula VI' , preferably Structure of Formula VI: [ka] Equation VI [In the formula, V″ is carbon; U is carbon and V is nitrogen, or U is nitrogen and V is carbon, and U, V and V″ are bonded to one or no hydrogen atoms according to valency; Ra is hydrogen, unsubstituted alkyl or substituted alkyl; R7 and R8 are independently not present (or absent), hydrogen, substituted alkyl, unsubstituted alkyl, cyano, halogen, hydroxyl, thiol, nitro-, unsubstituted alkoxy, substituted alkoxy, unsubstituted aroxy, substituted aroxy, substituted aryl, unsubstituted aryl, or adjacent R7 groups or adjacent R8 groups taken together with the atoms in the ring to which they are attached are independently 5- or 6-membered substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C3-C4 20 Cycloalkenyl, unsubstituted C3-C 20 forming (or producing) a cycloalkenyl, or a condensed combination thereof, n3 and n4 are independently an integer from 0 to 5, for example, 0, 1, 2, 3, 4, or 5. has.

[0070] In some embodiments, the compound is as described above for formula VI, except that the compound has the structure of formula VII': [ka] Formula VII' , preferably Structure of Formula VII: [ka] Formula VII [In the formula, Rv is absent (or non-existent or absent), hydrogen, substituted alkyl or unsubstituted alkyl; R7 and R8 are independently hydrogen, substituted alkyl, unsubstituted alkyl, unsubstituted aryl, halogen, cyano, or Rv and R7, taken together with the atoms in the ring to which they are attached, represent a 5- or 6-membered substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 cycloalkenyl, or a condensed combination thereof. has.

[0071] In some embodiments, the compound is as described above for Formula VI or Formula VII, except that: Rv is not present (or absent) or hydrogen; R7 and R8 are independently hydrogen, iso-propyl, tert-butyl, phenyl, fluorine or cyano; Rv and R7 together [ka] Form (or generate).

[0072] In some embodiments, the compound is as described above for any of Formulas I-VII, except that: R1 and R2 are independently hydrogen, substituted alkyl, unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, substituted aryl, unsubstituted aryl, or R1 and R2, together with the atoms in the ring to which they are attached, form (or generate) an unsubstituted aryl, substituted aryl, unsubstituted heteroaryl, or substituted heteroaryl. In some embodiments, R1 and R2 are hydrogen. In some embodiments, R1 and R2 together form the following structure: [ka] Form (or generate).

[0073] In some embodiments, the compound is as described above for any of Formulas I-VII, except that the compound has the structure of Formula VIII': [ka] Formula VIII' , preferably Structure of Formula VIII: [ka] Formula VIII having (i) M=Cu(I);W=N;Ra=H;U=CH;V=V''=carbon;Rv=H;R7=R8=H; (ii) M=Cu(I);W=N;Ra=H;U=CH;V=V''=carbon;Rv=H;R7=H;R8=CN; (iii) M=Cu(I); W=N; Ra=H; U=CH; V=V″=carbon; Rv=H; R7=R8=tert-butyl; (iv) M=Cu(I); W=N; Ra=H; U=CH; V=V″=carbon; Rv=H; R7=R8=phenyl; (v) M=Cu(I);W=N;Ra=H;U=CH;V=N;V''=carbon;Rv=absent;R7=R8=H; (vi) M=Cu(I); W=U=CH; V=V″=carbon; Rv=H; Ra=iso-propyl; R7=R8=H; (vii) M=Cu(I); W=N; Ra=H; U=CH; V=V''=carbon; R8=H; Rv and R7 together are [ka] Form (or generate); (viii) M=Cu(I); W=U=CH; Ra=iso-propyl; V=V″=carbon; R8=H; Rv and R7 together are [ka] Form (or generate); (ix) M=Cu(I);W=N;Ra=H;U=CH;V=V''=carbon;Rv=H;R7=R8=H; (x) M=Cu(I);W=N;Ra=H;U=CH;V=V''=carbon;Rv=H;R7=H;R8=F; (xi) M=Cu(I); W=N; Ra=H; U=CH; V=V″=carbon; Rv=H; R7=R8=methyl; (xii) M=Au(I); W=N; Ra=H; U=CH; V=carbon; Rv=H; V''=carbon; R7=R8=H; (xiii) M=Au(I); W=N; Ra=H; U=CH; V=carbon; Rv=H; V''=carbon; R7=H, R8=CN; (xiv) M=Au(I); W=N; Ra=H; U=N; V=carbon; Rv=H; V''=carbon; R7=R8=H; (xv) M=Au(I);W=U=CH;V=carbon;Rv=H;;Ra=iso-propyl;V''=carbon;R7=R8=H; (xvi) M=Au(I); W=N; Ra=H; U=CH; V=N; Rv=absent; V''=carbon; R7=R8=H; (xvii) M=Au(I);W=N;Ra=H;U=CH;V=V''=carbon;Rv=H;R7=R8=CN; (xviii) M=Au(I); W=N; Ra=hydrogen; U=CH; V=V″=carbon; R8=H; Rv and R7 together are [ka] Form (or generate); (xix) M=Au(I); W=U=CH; Ra=iso-propyl; V=V″=carbon; Rv=H; R7=R8=tert-butyl; (xx) M = Au(I); W = U = CH; Ra = iso-propyl; V = V'' = carbon; Rv = H; R7 = H; R8 = F; (xxi) M=Au(I); W=N; U=CH; Ra=H; V=V''=carbon; Rv=H; R7=R8=H; (xxii) M=Au(I); W=N; U=CH; Ra=H; V=V″=carbon; Rv=H; R7=R8=tert-butyl; (xxiii) M=Ag(I);W=N;U=CH;Ra=H;V=V''=carbon;Rv=H;R7=R8=H; For (i), (ii), (iii), (iv), (v), (vi), (vii), (viii), (xii), (xiii), (xiv), (xv), (xvi), (xvii), (xviii), (xix), (xx) and (xxiii), a dashed line indicates the absence (or absence or absence) of a bond; For (ix), (x), (xi), (xxi) and (xxii), the dashed line indicates the existence (or presence) of a bond.

[0074] In some embodiments, the compound is: [ka] [ka] [ka] [Wherein M=Cu(I), Au(I) or Ag(I)] The structure is selected from:

[0075] In some embodiments, the compound is as described above for any of Formulas I-VII, except that substituted is halogen, hydroxyl, thiol, nitro-, unsubstituted alkyl, unsubstituted alkenyl, unsubstituted alkynyl, unsubstituted aryl, unsubstituted heteroaryl, unsubstituted arylalkyl, unsubstituted alkoxy, unsubstituted aroxy, unsubstituted alkylthio, unsubstituted arylthio, cyano, isocyano, unsubstituted carbonyl, unsubstituted carboxyl, oxo (=O), unsubstituted amino, unsubstituted amido, unsubstituted sulfonyl, unsubstituted sulfonic acid, unsubstituted phosphoryl, unsubstituted phosphonyl, unsubstituted polyaryl, or unsubstituted C3-C 20 It is meant to be substituted with one or more substituents selected from cycloalkyl and unsubstituted heterocyclyl.

[0076] In some embodiments, the compound has a photoluminescence quantum yield (PLQY) of 0.50 to 0.95, e.g., 0.58 to 0.92 (thin film). In some embodiments, the compound has an emission decay lifetime (τ) of 0.20 μs to 0.45 μs, e.g., 0.23 μs to 42 μs (thin film). In some embodiments, the compound has a PLQY of 0.50 to 0.95, for example, 0.58 to 0.92, and a luminescence decay lifetime (τ) of 0.20 μs to 0.45 μs, for example, 0.23 μs to 42 μs (thin film). In some embodiments, the radiative rate constant of the compound is between 10 and 35×10 5 s -1 , e.g., 15 to 21 × 105 s -1 or about 29 x 10 5 s -1 (thin film). The film may also include an organic compound. Exemplary organic compounds include, but are not limited to, host materials such as 1,3-bis(N-carbazolyl)benzene (mCP), 2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan (PPF), bis[2-(diphenylphosphino)phenyl]etheroxide (DPEPO), 3,3'-di(9H-carbazol-9-yl)-1,1'-biphenyl (mCBP), poly(methyl methacrylate) (PMMA), polystyrene (PS), or combinations thereof.

[0077] In some embodiments, the compound acts as a sensitizer (or sensitizer or sensitizer) to transfer energy (e.g., exciton energy (or exciton energy) or photon energy (or photon energy)) to a pure organic emitter (or pure organic emitter). In some embodiments, the compounds act as sensitizers, transferring energy (e.g., exciton energy or photon energy) to pure organic emitters that exhibit thermally activated delayed fluorescence. In some forms, the compound acts as a sensitizer (or sensitizer or sensitizer) to transfer energy (e.g., exciton energy (or exciton energy) or photon energy (or photon energy)) to a pure organic emitter (or pure organic emitter). The pure organic emitter is a boron-based (or boron-based) emitter. As used throughout this application, the phrase "pure organic emitter" refers to light-emitting organic molecules formed exclusively from main group elements of the periodic table such that the light-emitting organic molecules do not contain covalent or dative bonds to main group metals. In particular, such phrases are not intended to define (or prescribe) or specify a level of purity of a composition that includes light-emitting organic molecules.

[0078] All compounds falling within the above definition (or definition) are intended to be, or should be considered to be, specifically disclosed herein. Furthermore, all subgroups identifiable in the above definition (or definition) are intended to be or should be considered to be specifically disclosed herein. As a result, it is specifically contemplated that any compound or subgroup of compounds may be specifically included for use or excluded from use, or included in or excluded from a list of compounds. For example, any one or more of the compounds described in this disclosure, compounds having the structures shown in this disclosure, or compounds referred to in the tables or examples of this disclosure can be specifically included or excluded from such sets or subgroups of compounds, or can be combined in any combination. Such specific sets, subgroups, inclusions, and exclusions may apply to any embodiment or aspect of the compositions and methods described in this disclosure. For example, a set of compounds that specifically excludes one or more particular compounds may be used or applied in the context of the compounds themselves (e.g., a list or set of compounds), compositions comprising the compounds (e.g., including pharmaceutical compositions), any one or more of the disclosed methods, or any combination thereof. The various sets and subgroups of compounds with such specific inclusions and exclusions may be used or applied in the context of the compounds themselves, compositions comprising one or more of the compounds, or any of the disclosed methods. All such various sets and subgroups of compounds, as well as various sets of compounds, compositions, and methods of using or applying such compounds, are to be considered as specifically and individually contemplated and specifically and individually described.

[0079] (III) Manufacturing method and reagents therefor (A) Compound The two-coordinate (or two-dentate or two-coordination) d10 metal carbene complexes (or d10 metal carbene complexes or d10 metal-carbene complexes) and their ligands (or ligands) can be synthesized using methods as described in this disclosure and known in the art of organic chemical synthesis. The target compound can be synthesized by reacting the corresponding pyrazine fused NHC ligand (or corresponding pyrazine fused NHC ligand) or a precursor of the corresponding pyrazine fused NHC ligand (or corresponding pyrazine fused NHC ligand) or a combination thereof with a d10 compound in a solvent or solution to generate (or form) a complex precursor (or complex precursor or complex precursor or complex precursor). Exemplary solvents include organic solvents such as tetrahydrofuran and dichloromethane. The complex precursor can be reacted with a second ligand (eg, carbazole) for a suitable period of time to generate (or form) the d10 metal carbene complex. Specific d10 metal carbene complexes, including those containing Cu(I), Ag(I), and Au(I), are disclosed in the Examples below.

[0080] (B) Organic light-emitting devices Also described are methods of making an organic light-emitting device (e.g., an OLED) that includes one or more of the d10 metal carbene complexes described above for any of Formulas I-VIII. Preferred methods for fabricating OLEDs include vacuum deposition or solution processing techniques (e.g., spin coating and ink printing (e.g., ink jet printing or roll-to-roll printing). Methods for fabricating OLEDs containing the d10 metal carbene complexes described in this disclosure are disclosed in the examples below.

[0081] (IV) How to use Preferably, the d10 metal carbene complexes described in the present disclosure are photostable and emissive at room temperature, low temperature, or a combination thereof. Thus, the compounds described in the present disclosure can be incorporated into OLEDs, organic photovoltaic cells (OPVs) and organic field-effect transistors (OFETs) or electrochemiluminescent cells (LEECs), and can be used in stationary visual display units, mobile visual display units, or illumination devices. Examples of units or devices (or equipment or apparatus) include commercial applications such as smartphones, televisions, monitors, digital cameras, tablet computers, keyboards, clothes, ornaments, garment accessories, wearable devices, medical monitoring devices, wall paper, advertisement panels, laptops, household appliances, office appliances, and lighting fixtures. Preferably, such a unit or device (or equipment or apparatus) normally operates (or runs) at room temperature.

[0082] In some embodiments, the compound may be included in a light emitting layer (or light emitting layer). In some embodiments, the light-emitting layer containing the pure organic emitter may include one or more compounds that act as sensitizers to transfer energy (e.g., exciton energy or photon energy) to the pure organic emitter. In some embodiments, one or more of the compounds has a higher singlet state than a pure organic emitter. In some embodiments, pure organic emitters exhibit thermally activated delayed fluorescence. In some forms, pure organic emitters (or pure organic emitters) are boron-based (or boron-based or boron-based) emitters. In some embodiments, a light-emitting layer (or light-emitting layer) may be included in the OLED.

[0083] The compounds of the present disclosure, methods of using the compounds, and methods of making the compounds can be further understood by the paragraphs (or items) or embodiments listed below.

[0084] [1] Structure of Formula I: [ka] Formula I A compound having the formula: The compound has an overall neutral, negative or positive charge, M is copper, silver or gold, the oxidation state of which is 0, +1, +2 or +3, preferably +1; P' has the structure of formula I' below: [ka] Formula I' D is carbon; T, J and W are independently carbon or nitrogen, at least one of T, J and W is nitrogen, and when T is carbon, J is nitrogen, or when T is nitrogen, J is carbon, and T, J and W are bonded to one or no hydrogen atoms according to valency; X and Y are independently carbon or nitrogen, at least one of X and Y is nitrogen, and X and Y are bonded to one or no hydrogen atoms according to valency; R1 and R2 are independently selected from 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 C3-C 20 Cycloalkyl, unsubstituted C3-C 20 Cycloalkyl, Substituted C2-C 20 Heterocyclyl, unsubstituted C2-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, J, D and R2 taken together form an unsubstituted aryl, a substituted aryl, an unsubstituted heteroaryl or a substituted heteroaryl; R3 and R4 are independently selected from hydrogen, 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 C3-C 20 Cycloalkyl, unsubstituted C3-C 20 Cycloalkyl, Substituted C2-C 20 Heterocyclyl, unsubstituted C2-C 20 Heterocyclyl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 Cycloalkenyl, substituted C3-C 20 Cycloalkynyl or unsubstituted C3-C 20 is cycloalkynyl, R3' and R4' are independently not present (or are non-existent or 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 C3-C20 Cycloalkyl, unsubstituted C3-C 20 Cycloalkyl, Substituted C2-C 20 Heterocyclyl, unsubstituted C2-C 20 Heterocyclyl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 Cycloalkenyl, substituted C3-C 20 Cycloalkynyl or unsubstituted C3-C 20 is cycloalkynyl, Z is a substituted heteroaryl, an unsubstituted heteroaryl, a substituted polyheteroaryl, an unsubstituted polyheteroaryl, a substituted polyheterocyclyl, an unsubstituted polyheterocyclyl, a substituted or unsubstituted heterocyclyl, or -NR a R b where R a and R b are independently hydrogen, substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C-C 20 Cycloalkyl, unsubstituted C3-C 20 cycloalkyl, substituted heterocyclyl, unsubstituted heterocyclyl, substituted alkyl or unsubstituted alkyl; (i) R3 and R4 are not both 3,5-dialkyl substituted aryl; (ii) R3 and R4 are not both 3,5-dialkyl substituted phenyl; (iii) R3 and R4 are not both 3,5-dimethylphenyl; (iv) R3 and R4 are not both 3,5-dimethylphenyl when M is Cu or Au; or (v) The compound is [ka] or [ka] Not a compound.

[0085] [2] Structure of Formula II: [ka] Formula II [In the formula, CY1 and CY2 are independently selected from substituted aryl, unsubstituted aryl, substituted polyaryl, unsubstituted polyaryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C3-C 20 Cycloalkyl, unsubstituted C3-C 20 Cycloalkyl, Substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 Cycloalkenyl, substituted C3-C 20 Cycloalkynyl or unsubstituted C3-C 20 cycloalkynyl] 3. The compound according to claim 1 (or paragraph), having the formula:

[0086] [3] The compound of claim 1 or 2, wherein R3' and R4' are absent.

[0087] [4] The compound of paragraph 2 or 3, wherein CY1 and CY2 are independently substituted aryl, unsubstituted aryl, substituted polyaryl or unsubstituted polyaryl.

[0088] [5] Item 5. The compound according to any one of items 2 to 4, wherein CY1 and CY2 are substituted aryl.

[0089] [6] Structure of Formula III: [ka] Formula III [In the formula, R5 and R6 are independently substituted or unsubstituted alkyl; n1 and n2 are independently an integer of 0 to 5, 1 to 5, 3 to 5 (e.g., 3); or an integer of 2 to 5 (e.g., 2). The compound according to any one of items 1 to 5, having the formula:

[0090] [7] Structure of Formula IV: [ka] Formula IV [In the formula, n1 and n2 are independently an integer of 1 to 5, 2 to 5, or 3 to 5; L is not present (or absent), a single bond, a substituted alkyl, -(CH2) nx -, oxygen, sulfur, or NRx, where nx is an integer from 1 to 3 (e.g., 1, 2, or 3), and Rx is unsubstituted alkyl, substituted alkyl, unsubstituted aryl, or substituted aryl; CY3 and CY4 are independently unsubstituted aryl, substituted aryl, unsubstituted polyaryl, substituted polyaryl, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, unsubstituted C3-C 20 Cycloalkyl, Substituted C3-C 20 Cycloalkyl, 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. The compound according to any one of items 1 to 6, having the formula:

[0091] [8] Structure of Formula V: [ka] Formula V [In the formula, Each Ra is independently hydrogen, unsubstituted alkyl, or substituted alkyl; Each Rb is independently unsubstituted or substituted alkyl; L is not present (or absent), a single bond, a substituted alkyl, -(CH2) nx -, oxygen, sulfur, or NRx, where nx is an integer from 1 to 3 (e.g., 1, 2, or 3) and Rx is unsubstituted alkyl, substituted alkyl, unsubstituted aryl, or substituted aryl; Optionally, at least one of X and Y is nitrogen. The compound according to any one of items 1 to 7, having the formula:

[0092] [9] (i) T is nitrogen, J is carbon and W is carbon, or (ii) T is nitrogen, J is carbon, and W is nitrogen, or (iii) T is carbon, J is nitrogen and W is carbon; or (iv) T is carbon, J is nitrogen and W is nitrogen; The compound according to any one of items 1 to 8.

[0093]

[10] Ra is independently hydrogen, unsubstituted alkyl or substituted alkyl; Rb is independently unsubstituted or substituted alkyl; 8. The compound according to claim 8 or 9.

[0094]

[11] P' is [ka] [In the formula, Ra is independently hydrogen, unsubstituted alkyl or substituted alkyl; Rb is independently unsubstituted alkyl or substituted alkyl. Selected from: The compound according to any one of items 1 to 10.

[0095]

[12] Ra is independently hydrogen, methyl, isopropyl, or -CH(C2H5)2; Rb is independently methyl, iso-propyl, or -CH(C2H5)2; The compound according to any one of items 8 to 11.

[0096]

[13] CY3 and CY4 are independently unsubstituted aryl, substituted aryl, unsubstituted polyaryl, substituted polyaryl, unsubstituted heteroaryl, substituted heteroaryl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 13. The compound according to any one of items 7 to 12, which is cycloalkenyl, or a condensed combination thereof.

[0097]

[14] CY3 and CY4 are independently unsubstituted aryl, substituted aryl, unsubstituted heteroaryl, substituted heteroaryl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 14. The compound according to any one of items 7 to 13, which is cycloalkenyl, or a condensed combination thereof.

[0098]

[15] Z has the following structure: [ka] having X1, X2, X3, X4, X5, X6, X7 and X8 are independently carbon or nitrogen; R x1 , R x2 , R x3 , R x4 , R x5 , R x6 , R x7 and R x8 are independently hydrogen, halogen, cyano, unsubstituted alkyl, substituted alkyl, unsubstituted alkoxy, substituted alkoxy, unsubstituted aryl, substituted aryl, unsubstituted heteroaryl or substituted heteroaryl; R x1 , R x2 , R x3 , R x4 , R x5 , R x6 , R x7 or R x8 When X1, X2, X3, X4, X5, X6, X7 or X8 corresponding to the above is nitrogen, or R x4 is a bond connecting to a substituent on L, or adjacent Rxn groups taken together with the atoms in the ring to which they are attached independently represent 5- or 6-membered substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 cycloalkenyl, or when they form a condensed combination (wherein adjacent R groups, n is a consecutive pair of integers from 1 to 4 or 5 to 8), R x1 , R x2 , R x3 , R x4 , R x5 , R x6 , R x7 or Rx8 are not present (or non-existent or absent), L is absent, a single bond, a substituted alkyl, -(CH2), nx -, oxygen, sulfur, or NRx, where nx is an integer from 1 to 3 (e.g., 1, 2, or 3), and Rx is unsubstituted alkyl, substituted alkyl, unsubstituted aryl, or substituted aryl; The compound according to any one of items 1 to 14.

[0099]

[16] Z has the following structure: [ka] having L' is substituted aryl, unsubstituted aryl, substituted heteroaryl or unsubstituted heteroaryl, preferably substituted aryl or unsubstituted aryl, preferably substituted phenyl or unsubstituted phenyl; The compound according to any one of items 1 to 15.

[0100]

[17] Z has the following structure: [ka] 16. The compound according to claim 15, having the formula:

[0101]

[18] R x1 , R x2 , R x3 , R x4 , R x5 , R x6 , R x7 and R x8 is independently hydrogen, halogen, methyl, cyano, trifluoromethyl, tert-butyl, methoxy, phenyl or pyridyl.

[0102]

[19] 19. The compound according to any one of items 1 to 18, wherein X and Y are nitrogen.

[0103]

[20] Structure of Formula VI': [ka] Formula VI' , preferably Structure of Formula VI: [ka] Equation VI [In the formula, V″ is carbon; U is carbon and V is nitrogen, or U is nitrogen and V is carbon, and U, V and V″ are bonded to one or no hydrogen atoms according to valency; Ra is hydrogen, unsubstituted alkyl or substituted alkyl; R7 and R8 are independently not present (or absent), hydrogen, substituted alkyl, unsubstituted alkyl, cyano, halogen, hydroxyl, thiol, nitro-, unsubstituted alkoxy, substituted alkoxy, unsubstituted aroxy, substituted aroxy, substituted aryl, unsubstituted aryl, or adjacent R7 groups or adjacent R8 groups taken together with the atoms in the ring to which they are attached are independently 5- or 6-membered substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C3-C4 20 Cycloalkenyl, unsubstituted C3-C 20 cycloalkenyl, or a condensed combination thereof; n3 and n4 are independently an integer from 0 to 5, for example, 0, 1, 2, 3, 4, or 5. 2. The compound according to claim 1, having the formula:

[0104] [twenty one] Structure of Formula VII': [ka] Formula VII' , preferably Structure of Formula VII: [ka] Formula VII [In the formula, Rv is absent (or non-existent or absent), hydrogen, substituted alkyl or unsubstituted alkyl; R7 and R8 are independently hydrogen, substituted alkyl, unsubstituted alkyl, unsubstituted aryl, halogen or cyano; Rv and R7, taken together with the atoms in the ring to which they are attached, represent a 5- or 6-membered substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C3-C 20 Cycloalkenyl, unsubstituted C3-C 20 cycloalkenyl, or a condensed combination thereof. 20. The compound according to claim 19, having the formula:

[0105] [twenty two] Rv is not present (or absent) or hydrogen; R7 and R8 are independently hydrogen, iso-propyl, tert-butyl, phenyl, fluorine or cyano; Rv and R7 together [ka] forming (or generating) 2. The compound according to claim 20 or 21.

[0106] [twenty three] R1 and R2 are independently hydrogen, substituted alkyl, unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, substituted aryl, unsubstituted aryl, or R1 and R2, together with the atoms in the ring to which they are attached, form an unsubstituted aryl, a substituted aryl, an unsubstituted heteroaryl or a substituted heteroaryl; The compound according to any one of items 20 to 22.

[0107] [twenty four] R1 and R2 are hydrogen or R1 and R2 taken together form the following structure: [ka] 24. The compound according to any one of items 20 to 23, which forms (or generates):

[0108] [twenty five] Structure of Formula VIII': [ka] Formula VIII' , preferably Structure of Formula VIII: [ka] Formula VIII having (i) M=Cu(I);W=N;Ra=H;U=CH;V=V''=carbon;Rv=H;R7=R8=H; (ii) M=Cu(I);W=N;Ra=H;U=CH;V=V''=carbon;Rv=H;R7=H;R8=CN; (iii) M=Cu(I); W=N; Ra=H; U=CH; V=V″=carbon; Rv=H; R7=R8=tert-butyl; (iv) M=Cu(I); W=N; Ra=H; U=CH; V=V″=carbon; Rv=H; R7=R8=phenyl; (v) M=Cu(I); W=N; Ra=H; U=CH; V=N; V″=carbon; Rv=absent (or absent); R7=R8=H; (vi) M=Cu(I); W=U=CH; V=V″=carbon; Rv=H; Ra=iso-propyl; R7=R8=H; (vii) M=Cu(I); W=N; Ra=H; U=CH; V=V''=carbon; R8=H; Rv and R7 together are [ka] Form (or generate); (viii) M=Cu(I); W=U=CH; Ra=iso-propyl; V=V″=carbon; R8=H; Rv and R7 together are [ka] Form (or generate); (ix) M=Cu(I);W=N;Ra=H;U=CH;V=V''=carbon;Rv=H;R7=R8=H; (x) M=Cu(I);W=N;Ra=H;U=CH;V=V''=carbon;Rv=H;R7=H;R8=F; (xi) M=Cu(I); W=N; Ra=H; U=CH; V=V″=carbon; Rv=H; R7=R8=methyl; (xii) M=Au(I); W=N; Ra=H; U=CH; V=carbon; Rv=H; V''=carbon; R7=R8=H; (xiii) M=Au(I); W=N; Ra=H; U=CH; V=carbon; Rv=H; V''=carbon; R7=H, R8=CN; (xiv) M=Au(I); W=N; Ra=H; U=N; V=carbon; Rv=H; V''=carbon; R7=R8=H; (xv) M=Au(I);W=U=CH;V=carbon;Rv=H;;Ra=iso-propyl;V''=carbon;R7=R8=H; (xvi) M=Au(I); W=N; Ra=H; U=CH; V=N; Rv=absent; V''=carbon; R7=R8=H; (xvii) M=Au(I);W=N;Ra=H;U=CH;V=V''=carbon;Rv=H;R7=R8=CN; (xviii) M=Au(I); W=N; Ra=hydrogen; U=CH; V=V″=carbon; R8=H; Rv and R7 together are [ka] Form (or generate); (xix) M=Au(I); W=U=CH; Ra=iso-propyl; V=V″=carbon; Rv=H; R7=R8=tert-butyl; (xx) M = Au(I); W = U = CH; Ra = iso-propyl; V = V'' = carbon; Rv = H; R7 = H; R8 = F; (xxi) M=Au(I); W=N; U=CH; Ra=H; V=V''=carbon; Rv=H; R7=R8=H; (xxii) M=Au(I); W=N; U=CH; Ra=H; V=V″=carbon; Rv=H; R7=R8=tert-butyl; (xxiii) M=Ag(I);W=N;U=CH;Ra=H;V=V''=carbon;Rv=H;R7=R8=H; For (i), (ii), (iii), (iv), (v), (vi), (vii), (viii), (xii), (xiii), (xiv), (xv), (xvi), (xvii), (xviii), (xix), (xx) and (xxiii), a dashed line indicates the absence (or absence or absence) of a bond; For (ix), (x), (xi), (xxi) and (xxii), the dashed line indicates the presence of a bond. 25. The compound according to claim 24.

[0109]

[26] The following structure: [ka] [ka] [ka] [Wherein M=Cu(I), Au(I) or Ag(I)] 2. The compound according to claim 1, having the formula:

[0110]

[27] Substituted means halogen, hydroxyl, thiol, nitro-, unsubstituted alkyl, unsubstituted alkenyl, unsubstituted alkynyl, unsubstituted aryl, unsubstituted heteroaryl, unsubstituted arylalkyl, unsubstituted alkoxy, unsubstituted aroxy, unsubstituted alkylthio, unsubstituted arylthio, cyano, isocyano, unsubstituted carbonyl, unsubstituted carboxyl, oxo, unsubstituted amino, unsubstituted amido, unsubstituted sulfonyl, unsubstituted sulfonic acid, unsubstituted phosphoryl, unsubstituted phosphonyl, unsubstituted polyaryl or unsubstituted C3-C 20 The compound according to any one of items 1 to 25, which means that it is substituted with one or more substituents selected from cycloalkyl and unsubstituted heterocyclyl.

[0111]

[28] 28. An organic electronic component comprising a compound according to any one of claims 1 to 27.

[0112]

[29] 29. The organic electronic component according to claim 28, 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).

[0113]

[30] 30. An organic electronic component according to claim 28 or 29, wherein the compound is contained in a light-emitting layer.

[0114]

[31] An anode; A cathode; A hole transport region; Electron transport region and The hole transport region comprises a hole injection layer and / or a hole transport layer, and optionally an electron blocking layer; the electron transport region comprises an electron transport layer and / or an electron injection layer, and optionally a 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; Item 31. The organic electronic component according to any one of items 28 to 30.

[0115]

[32] 31. The organic electronic component of claim 29 or 30, wherein the light-emitting layer is formed (or manufactured) by vacuum deposition, spin coating or ink printing (e.g. ink-jet printing or roll-to-roll printing).

[0116]

[33] 28. A light-emitting layer comprising the compound according to any one of items 1 to 27.

[0117]

[34] 28. An emissive layer comprising the compound according to any one of claims 1 to 27 and a pure organic emitter, wherein the compound acts as a sensitizer for transferring energy (e.g., exciton energy or photon energy) to the pure organic emitter.

[0118]

[35] 28. An emissive layer comprising the compound according to any one of claims 1 to 27 and a pure organic emitter, wherein the compound has a higher singlet state than the pure organic emitter.

[0119]

[36] 28. An emissive layer comprising the compound according to any one of claims 1 to 27 and a pure organic emitter, wherein the compound acts as a sensitizer for transferring energy (e.g., exciton energy or photon energy) to the pure organic emitter, and the emitter exhibits thermally activated delayed fluorescence.

[0120]

[37] 28. An emissive layer comprising the compound according to any one of claims 1 to 27 and a pure organic emitter, wherein the compound acts as a sensitizer for transferring energy (e.g. exciton energy or photon energy) to the pure organic emitter, and the emitter is a boron-based (or boron-based or boron-based) emitter.

[0121]

[38] 38. An OLED (or organic light-emitting diode (or organic light-emitting diode)) comprising an emitting layer according to any one of items 33 to 37.

[0122]

[39] 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. Item 39. A device (or apparatus or equipment) comprising the OLED according to item 38, selected from the group consisting of: EXAMPLES

[0123] (Example) Several d10 metal (Cu(I), Ag(I) or Au(I)) carbene complexes supported by pyrazine-fused N-heterocyclic carbene (NHC) ligands and carbazole derivatives have been prepared. These complexes exhibit efficient TADF properties, have high photoluminescence quantum yields (0.58-0.92) and short emission decay lifetimes (0.23-0.42 μs) in 1,3-bis(N-carbazolyl)benzene (mCP) thin films. The radiative decay rate constants of such complexes are obviously high, and the k of Cu(I) complexes is significantly higher than that of the other complexes. r is 15~21×10 5 s -1 and k of the Au(I) complex r is approximately 29 x 10 5 s -1 Both of these are supported by the k-type cyclic (alkyl)(amino)carbenes (CAACs) (Nature Communications 2020, 11, 1758; Chem. Sci. 2020, 11, 435), monoamido-aminocarbenes (MACs) (J. Am. Chem. Soc. 2019, 141, 3576-3588) or diamidocarbenes (DACs) (J. Am. Chem. Soc. 2019, 141, 3576-3588) of their previously reported Cu(I) counterparts. r (0.38~10×10 5 s -1 ) and its Au(I) counterpart k r (0.53~22×10 5 s -1 ) is greater than

[0124] In these two-coordinate (or two-conformation or two-coordination) d10 metal carbene complexes, the use of pyrazine- or pyridine-fused NHC ligands modified with bulky 2,6-diisopropylphenyl (DIPP) side groups is believed to result in improved properties of the disclosed d10 metal carbene complexes. The ligand structure improves the chemical and electrochemical stability, improves the electroluminescence performance by suppressing the distortion of the excited state structure, and improves the photoluminescence quantum yield. The electroluminescent performance, i.e. ultra-high device luminance and significantly longer device lifetime, is unmatched for D10 emitters. Furthermore, the emission color of this class of emitters can be tuned (changing the donor strength) by using carbazole derivatives. For example, green (Cu2 and Au2), yellow (Cu1, Au1 and Ag1) and red (Cu3) emitters have been prepared.

[0125] Example 1 Synthesis and characterization of compounds material and method Chemical reagents used in the synthesis were purchased from commercial sources (e.g., Dieckmann, Tiv Scientific, J & K Scientific, BLDpharm, Bidepharm). These were used directly without further treatment. Solvents used in the synthesis were purchased from Duksan, RCI Labscan, Scharlau. These were used directly without further treatment.

[0126] (i) Synthesis of pyrazine-fused N-heterocyclic carbene ligands (or pyrazine-fused N-heterocyclic carbene ligands) or pyridine-fused N-heterocyclic carbene ligands (or pyridine-fused N-heterocyclic carbene ligands)

[0127] Scheme 1 shows the synthesis of pyrazine-fused NHC ligands (or pyrazine-fused NHC ligands). [ka]

[0128] (a) Synthesis of N,N'-bis(2,6-diisopropylphenyl)pyrazine-2,3-diamine To a 1 M solution of lithium hexamethyldisilazide (LiHMDS) in THF (3.5 equiv.) in a sealed tube was added 2,6-diisopropylaniline (3.0 equiv.). The resulting mixture was stirred under argon for 30 min. 2,3-Dichloropyrazine (1.0 eq) was then added to the reaction mixture and heated at 80° C. overnight. After the reaction, the solvent was evaporated to dryness and the residue was extracted with DCM, which was then purified by column chromatography. 1 H NMR (500 MHz, CDCl3) δ / ppm 7.49 (s, 1H), 7.34 - 7.30 (m, 1H), 7.24 (d, J = 7.6 Hz, 2H), 5.72 (s, 1H), 3.10 (dt, J = 13.5, 6.7 Hz, 2H), 1.19 (d, J = 6.7 Hz, 16H). 13C NMR (100 MHz, CDCl3) δ / ppm 146.10, 144.34, 133.84, 132.40, 127.98, 124.03, 28.98, 23.88. HRESI-MS [M+H] + ( [C 28 H 38 N4] + ), calculated m / z: 431.3169, found: 431.3168.

[0129] (b) Synthesis of 1,3-bis(2,6-diisopropylphenyl)imidazo[4,5-b]pyrazine-3-ium chloride (PzIm-Cl) N,N'-bis(2,6-diisopropylphenyl)pyrazine-2,3-diamine (1.2 mmol) in triethyl orthoformate (or triethyl orthoformate) was added to a round bottom flask. The mixture was heated at 150° C. for 6 hours. The mixture was then cooled to room temperature and an excess of chlorotrimethylsilane was added. The resulting reaction mixture was heated at 70° C. overnight. After the reaction, the precipitate was collected by filtration, washed with Et2O, and dried in air to give an off-white solid. 1 H NMR (500 MHz, CDCl3) δ / ppm 13.64 (br s, 1H), 8.87 (s, 2 H), 7.66 (t, J = 7.5 Hz, 2 H), 7.42 (d, J = 8.0 Hz, 4 H), 2.99 (m, 4 H), 1.30 - 1.12 (m, 24 H). 13 C NMR (100 MHz, CDCl3) δ / ppm 145.66, 145.02, 137.87, 132.73, 126.21, 124.98, 30.04, 24.62, 23.53. HRESI-MS [M-Cl] + ([C 29 H 37 N4] +), calculated m / z: 441.3013, found: 441.3013.

[0130] Scheme 2 shows the synthesis of pyridine-fused NHC ligands (or pyridine-fused NHC ligands). [ka]

[0131] (c) Synthesis of 2-chloro-N-(2,4,6-triisopropylphenyl)pyridin-3-amine A mixture of 2-chloropyridin-3-amine (1.28 g, 10 mmol), (diacetoxyiodo)benzene (15 mmol) and triisopropylbenzene (100 mmol) in 1,1,1,3,3,3-hexafluoro-2-propanol (40 mL) was stirred at room temperature overnight. After the reaction, the solvent was evaporated and the residue was purified by column chromatography. Yield: 2.85 g, 86%. 1 H NMR (500 MHz, CDCl3) δ / ppm 7.73 (d, J = 4.2 Hz, 1H), 7.08 (s, 2H), 6.95 (dd, J = 8.0, 4.6 Hz, 1H), 6.45 (d, J = 7.9 Hz, 1H), 5.63 (s, 1H), 3.02 (dt, J = 13.7, 6.9 Hz, 2H), 2.93 (dt, J = 13.8, 6.9 Hz, 1H), 1.29 (d, J = 6.9 Hz, 6H), 1.18 (s, 6H), 1.10 (d, J = 6.8 Hz, 6H). 13C NMR (101 MHz, CDCl3) δ / ppm 148.90, 147.37, 141.30, 137.21, 136.38, 130.83, 123.54, 122.29, 119.07, 77.55, 77.23, 76.91, 34.48, 28.66, 24.79, 24.29, 23.39. HRESI-MS: [M+H] + ([C 20 H 27 N2Cl] + ), calculated m / z: 331.1936, found: 331.1933.

[0132] (d) N 2 -(2,6-diisopropylphenyl)-N 3 -(2,4,6-triisopropyl Synthesis of (phenyl)-pyridine-2,3-diamine P in toluene (20 mL) t To a solution of Bu3 (100 mg, 0.50 mmol) was added Pd2(aba)3 (100 mg, 0.11 mmol). The dark red solution was stirred at room temperature for 5 min. This solution was then treated with 2,6-diisopropylaniline (355 mg, 2.0 equiv.), 2-chloro-N-(2,4,6-triisopropylphenyl)pyridin-3-amine (330 mg, 1.0 equiv.) and NaO t Bu (289 mg, 3.0 equiv.) was added (one port). The resulting solution was heated at 130° C. for 2 days. After the reaction, the solution was passed through a pad of Celite and evaporated to dryness. The residue was purified by column chromatography (silica gel). Yield: 167 mg, 35%. 1H NMR (500 MHz, CDCl3) δ / ppm 7.69 (d, J = 4.2 Hz, 1H), 7.36 - 7.31 (m, 1H), 7.29 (d, J = 7.3 Hz, 2H), 7.13 (s, 2H), 6.58 - 6.49 (m, 2H), 6.06 (s, 1H), 4.82 (s, 1H), 3.25 (dt, J = 13.7, 6.8 Hz, 2H), 3.13 (dt, J = 13.6, 6.8 Hz, 2H), 2.98 (dt, J = 13.8, 6.9 Hz, 1H), 1.26 (d, J = 5.7 Hz, 24H), 1.20 (s, 6H). 13 C NMR (101 MHz, CDCl3) δ / ppm 149.50, 146.83, 145.88, 144.72, 139.01, 135.13, 133.35, 131.35, 127.06, 123.63, 121.94, 121.11, 114.82, 34.22, 28.77, 28.36, 24.20. HRESI-MS: [M+H] + ([C 32 H 45 N3] + ), calculated m / z: 472.3686, found: 472.3680.

[0133] (e) Synthesis of 3-(2,6-diisopropylphenyl)-1-(2,4,6-triisopropylphenyl)-1H-imidazo[4,5-b]pyridin-3-ium tetrafluoroborate (PyIPr-BF4) N 2 -(2,6-diisopropylphenyl)-N 3 -(2,4,6-triisopropylphenyl)-pyridin-2,3-amine (500 mg, 1.06 mmol) in triethyl orthoformate (or triethyl orthoformate) The mixture was then heated at 150° C. for several hours. The mixture was then cooled to room temperature and an excess of chlorotrimethylsilane was added. The resulting reaction mixture was heated at 70° C. overnight. After the reaction, the solvent was evaporated and HBF4 (in methanol) was added and stirred at room temperature for 30 minutes. The solution was then extracted with dichloromethane and saturated aqueous NaHCO3, and the organic layer was dried over MgSO4 and evaporated to give a white solid (3-(2,6-diisopropylphenyl)-1-(2,4,6-triisopropylphenyl)-1H-imidazo[4,5-b]pyridin-3-ium tetrafluoroborate salt). 1 H NMR (500 MHz, CDCl3) δ / ppm 10.32 (s, 1H), 8.85 (d, J = 4.4 Hz, 1H), 7.90 (d, J = 8.3 Hz, 1H), 7.76 (dd, J = 8.2, 4.6 Hz, 1H), 7.66 (d, J = 7.8 Hz, 2H), 7.45 (d, J = 7.8 Hz, 3H), 7.27 (s, 2H), 3.04 (dt, J = 13.6, 6.8 Hz, 2H), 2.22 (td, J = 13.4, 6.6 Hz, 5H), 1.35 (d, J = 6.8 Hz, 7H), 1.28 (dd, J = 6.5, 2.9 Hz, 15H), 1.13 (t, J = 6.2 Hz, 15H). 19 F NMR (471 MHz, CDCl3) δ / ppm -151.89, -151.94. 11 B NMR (160 MHz, CDCl3) δ -1.31. 13 C NMR (126 MHz, CDCl3) δ / ppm 153.89, 151.06, 146.34, 145.86, 145.57, 144.31, 132.77, 126.57, 126.18, 125.08, 124.63, 124.29, 123.47, 123.06, 34.73, 30.01, 29.80, 24.55, 24.09, 24.02, 23.91. HRESI-MS: [M-BF4] + ([C 33 H 44 N3] + ), calculated m / z: 482.3529, found: 482.3516.

[0134] (ii) Synthesis of metal carbene complexes (or metal carbene complexes or metal-carbene complexes) Scheme 3 shows the synthesis of metal carbene complexes (or metal carbene complexes or metal-carbene complexes). [ka] [ka]

[0135] (a) Synthesis of Complex Precursor (or Complex Precursor or Complex Precursor or Complex Precursor or Complex Precursor) PzImCuCl KO t To a solution of Bu (1.2 equiv.) in THF was added PzIm-Cl (1.0 equiv.) and CuCl (1.2 equiv.). The resulting mixture was stirred at room temperature under argon overnight. After the reaction, the reaction mixture was passed through a layer of celite and then evaporated to dryness. The product was washed with EtOH and n-hexane. 1 H NMR (500 MHz, CDCl3) δ / ppm 1 H NMR (500 MHz, CDCl3) δ 8.52 (s, 2H), 7.62 (t, J = 7.5 Hz, 2H), 7.42 (d, J = 7.6 Hz, 4H), 2.38 - 2.27 (m, 4H), 1.30 (d, J = 6.2 Hz, 12H), 1.12 (d, J = 6.4 Hz, 12H). 13C NMR (126 MHz, CDCl3) δ / ppm 193.51, 146.31, 141.20, 140.18, 131.81, 130.38, 124.93, 29.63, 24.94, 23.84.

[0136] (b) Synthesis of Complex Precursor (or Complex Precursor or Complex Precursor or Complex Precursor or Complex Precursor) PzImAuCl A suspension of PzIm-Cl (1.0 equiv.) in THF was added to t Bu (1.2 equiv.) was added and the resulting mixture was stirred at room temperature under argon for 1 h, over which time a solution formed which gradually turned clear. Au(tht)Cl (1.2 eq.) was then added and the reaction mixture was left to stir in the dark for 16 h. After the reaction, the mixture was filtered through a pad of celite and then evaporated to dryness. The product was washed with EtOH and n-hexane. Yield: 185 mg, 27%. 1 H NMR (500 MHz, CDCl3) δ / ppm 8.55 (s, 2H), 7.63 (t, J = 7.8 Hz, 2H), 7.41 (d, J = 7.8 Hz, 4H), 2.33 (dt, J = 13.8, 6.9 Hz, 4H), 1.34 (d, J = 6.9 Hz, 12H), 1.10 (t, J = 7.9 Hz, 12H). 13 C NMR (126 MHz, CDCl3) δ / ppm 188.22, 146.16, 141.49, 139.91, 131.70, 129.88, 124.75, 29.50, 24.40, 23.82.

[0137] (c) Synthesis of Complex Precursor (or Complex Precursor or Complex Precursor or Complex Precursor or Complex Precursor) PzImAgCl To a solution of PzIm-Cl (1.0 equiv.) in DCM was added Ag2O (1.0 equiv.). The resulting suspension was stirred overnight at room temperature in the dark. After the reaction, the reaction mixture was filtered through a pad of Celite and then evaporated to dryness. The product was washed with EtOH and n-hexane. 1 H NMR (500 MHz, CDCl3) δ / ppm 8.56 (s, 1H), 7.63 (t, J = 7.7 Hz, 1H), 7.42 (d, J = 7.8 Hz, 2H), 2.31 (dt, J = 13.5, 6.8 Hz, 3H), 1.28 (d, J = 6.8 Hz, 7H), 1.11 (d, J = 6.7 Hz, 8H). 13 C NMR (126 MHz, CDCl3) δ / ppm 146.32, 141.47, 140.12, 131.97, 130.65, 125.06, 29.60, 24.86, 23.96.

[0138] (d) General procedure for the synthesis of complexes A solution of a carbazole derivative (1.5 equivalents) in THF or a solution of a pyrido[3,4-b]indole derivative (1.5 equivalents) in THF was added to NaO t Bu (1.5 equiv.) was added and the mixture was stirred at room temperature under argon for 30 min. NHC-M-Cl (1.0 equiv.) was then added and the reaction mixture was stirred overnight in the dark. After the reaction, the mixture was passed through a pad of Celite. The filtrate was evaporated to dryness and the product was washed with n-hexane.

[0139] Cu1: 1H NMR (500 MHz, CD2Cl2) δ / ppm 8.59 (s, 2H), 7.85 (d, J = 7.6 Hz, 4H), 7.59 (d, J = 7.8 Hz, 2H), 6.96 (t, J = 7.7 Hz ( 6, = 2H), 2H), 6.23 (d, J = 8.1 Hz, 2H), 2.54 - 2.45 (m, 4H), 1.26 (d, J = 6.8 Hz, 12H), 1.18 (d, J = 6.8 Hz, 12H). 13 C NMR (126 MHz, CD2Cl2) δ / ppm 194.61, 149.71, 146.96, 141.06, 140.27, 131.49, 130.91, 124.84, 123,12.84.0, 1 115.44, 114.06, 29.52, 24.42, 23.50.

[0140] Cu2: 1 H NMR (500 MHz, CD2Cl2) δ / ppm 8.59 (s, 2H), 8.16 (s, 1H), 7.90 − 7.79 (m,3H), 7.58 (d, J = 7.3 Hz, 4H), 7.17 (Ht, J = 1 = Hz, 7.5 Hz, 1H), 6.95 (t, J = 6.9 Hz, 1H), 6.27 (d, J = 7.8 Hz, 1H), 6.12 (d, J = 8.5 Hz, 1H), 2.46 (m, 4H), 1,22 (6.16 (d, J = Hz). 6.1 Hz, 12H). 13C NMR (151 MHz, CD2Cl2) δ / ppm 194.40, 152.20, 150.93, 147.54, 141.87, 140.72, 132.15, 131.40, 127 12.5.4, 1 124.98, 124.60, 123.85, 122.50, 120.14, 117.89, 115.16, 114.93, 97.47, 30.08, 25.02, 24.04.

[0141] Cu3: 1 H NMR (500 MHz, CD2Cl2) δ / ppm 8.58 (s, 2H), 7.87 − 7.80 (m, 4H), 7.60 (d, J = 7.8 Hz, 4H), 7.02 (d, J = 8.5 Hz, J. = 2H (d. 6), 2.50 (dt, J = 13.5, 6.7 Hz, 4H), 1.37 (s, 18H), 1.28 (d, J = 6.8 Hz, 12H), 1.18 (d, J = 6.7 Hz, 12H). 13 C NMR (126 MHz, CD2Cl2) δ / ppm 195.21, 148.72, 147.33, 141.40, 140.69, 138.38, 131.88, 131.31, 125,21.8, 1 115.42, 113.75, 34.70, 32.36, 29.93, 24.89, 23.90.

[0142] Cu4: 11H NMR (500 MHz, CD2Cl2) δ / ppm 8.61 (s, 2H), 8.18 (s, 2H), 7.87 (t, J = 7.9 Hz, 2H), 7.68 (d, J = 7.6 Hz, 4H), 7.62 (d, J = 7.9 Hz, 4H), 7.42 (t, J = 7.5 Hz, 4H), 7.30 (d, J = 8.3 Hz, 2H), 7.25 (t, J = 7.3 Hz, 2H), 6.30 (d, J = 8.4 Hz, 2H), 2.52 (dq, J = 13.8, 6.9 Hz, 4H), 1.30 (d, J = 6.8 Hz, 12H), 1.20 (d, J = 6.7 Hz, 12H). 13 13C NMR (126 MHz, CD2Cl2) δ / ppm 194.85, 150.39, 147.42, 143.41, 141.56, 140.68, 131.98, 131.34, 129.28, 128.96, 127.16, 125.89, 125.31, 125.10, 123.66, 118.10, 114.85, 29.97, 24.90, 23.93. MALDI-TOF: [C 53 H 52 CuN5] m / z Calculated value m / z: 821.35, Measured value: 821.28. Analytical calculated value (C 53 H 52 CuN5 + H2O): C, 75.73; H, 6.48; N, 8.33; Measured value: C, 75.71; H, 6.26; N, 8.10.

[0143] Cu5: 1H NMR (500 MHz, CD2Cl2) δ / ppm 8.64 (s, 2H), 8.03 (d, J = 3.9 Hz, 1H), 7.96 (d, J = 7.8 Hz, 1H), 7.89 (t, J = 7.9 Hz (d 7, = 2H), 1H), 7.70 (s, 1H), 7.63 (d, J = 7.9 Hz, 4H), 7.12 (t, J = 7.4 Hz, 1H), 6.96 (t, J = 7.3 Hz, 1H), 6.30 (d, J = 8.5 (H3 Hz), 1H t2, 6.8 Hz, 4H), 1.29 (d, J = 6.8 Hz, 12H), 1.21 (d, J = 6.8 Hz, 12H).

[0144] Au1: 1 H NMR (400 MHz, CD2Cl2) δ / ppm 8.58 (s, 2H), 7.87 (d, J = 7.6 Hz, 2H), 7.79 (t, J = 7.9 Hz, 2H), 7.54 (d, J = 7.9 - 7. 2H), ( m 7. 4H), 6.91 - 6.82 (m, 2H), 6.61 (d, J = 8.1 Hz, 2H), 2.48 (dt, J = 13.7, 6.9 Hz, 4H), 1.32 (d, J = 6.9 Hz, 12H), H 1, = 1.14 (1.9 Hz). 13 C NMR (126 MHz, CD2Cl2) δ / ppm 149.77, 147.49, 141.94, 140.93, 132.07, 131.13, 125.29, 124.25, 174,191.6, 1 113.92, 30.15, 24.59, 24.31.

[0145] Au2: 1H NMR (500 MHz, CD2Cl2) δ / ppm 8.61 (s, 1H), 8.20 (s, 0H), 7.91 (d, J = 7.7 Hz, 1H), 7.80 (t, J = 7.8 Hz, 1H), 7.55 (d, J = 7.8 Hz, 2H), 7.26 (d, J = 8.4 Hz, 0H), 7.13 (t, J = 7.6 Hz, 1H), 6.99 (t, J = 7.4 Hz, 1H), 6.66 (d, J = 8.2 Hz, 0H), 6.56 (d, J = 8.4 Hz, 1H), 2.46 (dt, J = 13.6, 6.8 Hz, 2H), 1.31 (d, J = 6.8 Hz, 6H), 1.15 (d, J = 6.8 Hz, 6H). 13 C NMR (126 MHz, CD2Cl2) δ / ppm 190.53, 151.14, 149.91, 146.94, 141.65, 140.23, 131.61, 130.47, 126.65, 125.11, 124.78, 124.51, 123.87, 123.08, 121.68, 119.63, 117.88, 113.96, 113.77, 97.74, 29.59, 24.04, 23.74.

[0146] Au3: 1 H NMR (500 MHz, CD2Cl2) δ / ppm 8.62 (s, 2H), 8.19 (dd, J = 10.7, 5.9 Hz, 2H), 7.92 (d, J = 7.8 Hz, 1H), 7.77 (t, J = 7.8 Hz, 2H), 7.55 (d, J = 7.8 Hz, 4H), 7.16 - 7.09 (m, 1H), 6.98 (t, J = 7.4 Hz, 1H), 6.90 - 6.83 (m, 1H), 6.72 (d, J = 8.1 Hz, 1H), 2.55 (dt, J = 13.1, 6.6 Hz, 4H), 1.44 (d, J = 6.8 Hz, 12H), 1.18 (d, J = 6.8 Hz, 12H). 13C NMR (126 MHz, CD2Cl2) δ / ppm 191.17, 148.59, 146.78, 145.01, 141.46, 140.29, 131.44, 130.46, 126.52, 124.69, 124.43, 121.92, 119.80, 116.83, 116.13, 113.65, 112.28, 29.59, 23.98, 23.67.

[0147] Ag1: 1 H NMR (500 MHz, CD2Cl2) δ / ppm 8.61 (s, 2H), 7.87 (d, J = 7.5 Hz, 2H), 7.75 (t, J = 7.7 Hz, 2H), 7.53 (d, J = 7.7 Hz, 4H), 7.02 (t, J = 7.4 Hz, 2H), 6.84 (t, J = 7.2 Hz, 2H), 6.57 (d, J = 8.0 Hz, 2H), 2.46 (dt, J = 13.1, 6.5 Hz, 4H), 1.30 (d, J = 6.6 Hz, 12H), 1.15 (d, J = 6.6 Hz, 12H). 13 C NMR (126 MHz, CD2Cl2) δ / ppm 150.27, 146.80, 141.55, 140.18, 131.69, 131.15, 124.93, 123.82, 123.41, 119.25, 115.08, 114.10, 29.57, 24.48, 23.71. Note: The carbon of carbenium 13 No C signal was observed.

[0148] Scheme 4 shows the synthesis of metal carbene complexes (or metal carbene complexes or metal-carbene complexes). [ka]

[0149] (e) General procedure for synthesizing the complex precursor (or complex precursor or complex precursor or complex precursor or complex precursor) PyIPr-M-Cl To a suspension of PyIPr-BF4 (1.0 equiv.) was added KHMDS (1.5 equiv.), followed by addition of CuCl or Au(tht)Cl (1.5 equiv.). The resulting mixture was stirred at room temperature under argon overnight. After the reaction, the suspension was passed through a layer of celite and evaporated to dryness. The product was purified by recrystallization (DCM / EtOH). PyIPrCuCl: 1 H NMR (500 MHz, CDCl3) δ / ppm 8.52 (dd, J = 4.7, 1.3 Hz, 1H), 7.58 (t, J = 7.8 Hz, 1H), 7.49 (dd, J = 8.1, 1.3 Hz, 1H), 7.40 (d, J = 7.8 Hz, 2H), 7.35 (dd, J = 8.2, 4.7 Hz, 1H), 7.21 (s, 2H), 3.03 (dt, J = 13.8, 6.9 Hz, 1H), 2.36 (tt, J = 13.6, 6.8 Hz, 4H), 1.36 (d, J = 6.9 Hz, 6H), 1.29 (d, J = 6.8 Hz, 12H), 1.11 (dd, J = 6.7, 5.7 Hz, 12H). 13 C NMR (101 MHz, CDCl3) δ / ppm 190.09, 151.93, 147.00, 146.75, 146.39, 146.08, 131.39, 130.95, 129.02, 127.64, 124.73, 122.94, 120.29, 120.18, 34.65, 29.46, 29.25, 25.28, 24.95, 24.14, 24.01, 23.76. HRESI-MS: [M-Cl+MeCN] + ([C 35 H 46 N4Cu] +), calculated m / z: 585.3013, found: 585.3026.

[0150] PyIPrAuCl: 1 H NMR (500 MHz, CDCl3) δ / ppm 8.54 - 8.51 (m, 1H), 7.59 (t, J = 7.8 Hz, 1H), 7.51 - 7.48 (m, 1H), 7.42 - 7.35 (m, 4H), 7.22 - 7.18 (m, 3H), 3.02 (dt, J = 13.8, 6.9 Hz, 1H), 2.40 - 2.28 (m, 6H), 1.37 (d, J = 6.9 Hz, 8H), 1.33 (d, J = 6.9 Hz, 16H), 1.09 (t, J = 6.4 Hz, 17H). 13 C NMR (101 MHz, CDCl3) δ / ppm 184.52, 151.83, 146.90, 146.44, 146.22, 145.89, 131.29, 130.48, 128.43, 127.37, 124.55, 122.80, 120.58, 120.20, 34.43, 29.32, 29.11, 24.73, 24.41, 24.01, 23.92, 23.71. HRESI-MS: [M-Cl+MeCN] + ([C 35 H 46 N4Au] + ), calculated m / z: 719.3388, found: 719.3378.

[0151] (f) General procedure for the synthesis of complexes A solution of a carbazole derivative (1.5 equiv.) in THF or a pyrido[3,4-b]indole derivative (1.5 equiv.) in THF was treated with NaO t Bu (1.5 equiv.) was added and the mixture was stirred at room temperature under argon for 30 min. PyIPr-M-Cl (1.0 equiv.) was then added and the reaction mixture was stirred overnight in the dark. After the reaction, the mixture was passed through a pad of Celite. The filtrate was evaporated to dryness and the product was washed with n-hexane.

[0152] Cu6: 1 H NMR (500 MHz, acetone-d6) δ / ppm 8.63 (dd, J = 4.7, 1.2 Hz, 1H), 7.98 (dd, J = 8.1, 1.2 Hz, 1H), 7.86 (t, J = 7.8 Hz, 1H), 7.81 (d, J = 7.6 Hz, 2H), 7.69 - 7.62 (m, 3H), 7.58 (s, 2H), 6.92 - 6.87 (m, 2H), 6.77 (t, J = 7.1 Hz, 2H), 6.32 (d, J = 8.1 Hz, 2H), 3.25 (dt, J = 13.8, 6.9 Hz,1H), 2.63 (ddt, J = 13.7, 10.6, 6.8 Hz, 4H), 1.50 (d, J = 6.9 Hz, 6H), 1.28 (dd, J = 14.1, 6.9 Hz, 12H), 1.22 (d, J = 6.9 Hz, 6H), 1.18 (d, J = 6.9 Hz, 6H). 13 C NMR (126 MHz, acetone-d6) δ / ppm 191.90, 153.21, 150.92, 148.10, 148.06, 147.77, 147.63, 132.81, 131.89, 130.58, 128.62, 125.50, 125.12, 124.18, 123.77, 121.83, 121.55, 119.83, 116.16, 115.05, 35.49, 25.34, 24.98, 24.59, 24.11, 23.98.

[0153] Cu7: 1H NMR (500 MHz, アセトン-d6) δ / ppm = 8.73 (s, 2H), 8.22 (s, 1H), 7.99-7.93 (m, 2H), 7.87 (d, J = 7.6 Hz, 1H), 7.74 (d, J = 7.8 Hz, 4H), 7.70 (d, J = 7.6 Hz, 1H), 7.40 (d, J = 7.4 Hz, 1H), 7.26-7.20 (m, 1H), 7.16-7.10 (m, 1H), 6.90-6.85 (m, 1H), 6.83-6.77 (m, 1H), 6.54 (s, 1H), 6.13 (d, J = 7.7 Hz, 1H), 2.73 (dd, J = 14.0, 7.3 Hz, 4H), 1.43 (s, 6H), 1.32 (d, J = 6.8 Hz, 12H), 1.20 (d, J = 6.7 Hz, 12H).

[0154] Cu8: 1 H NMR (500 MHz, アセトン-d6) δ / ppm 8.63 (d, J = 4.6 Hz, 1H), 8.23 (s, 1H), 7.94 (t, J = 7.6 Hz, 2H), 7.88 (d, J = 7.6 Hz, 1H), 7.71 (dd, J = 12.6, 7.7 Hz, 3H), 7.65 (dd, J = 8.0, 4.4 Hz, 1H), 7.60 (s, 2H), 7.40 (d, J = 7.3 Hz, 1H), 7.22 (t, J = 7.3 Hz, 1H), 7.12 (t, J = 7.3 Hz, 1H), 6.89 (t, J = 7.4 Hz, 1H), 6.79 (t, J = 7.3 Hz, 1H), 6.60 (s, 1H), 6.24 (d, J = 8.0 Hz, 1H), 3.27 (dt, J = 13.7, 6.8 Hz, 1H), 2.72-2.61 (m, 4H), 1.51 (d, J = 6.9 Hz, 6H), 1.41 (s, 6H), 1.32 (d, J = 6.8 Hz, 12H), 1.21 (dd, J = 14.6, 6.8 Hz, 12H).

[0155] Au4: 1 H NMR (500 MHz, CD2Cl2) δ / ppm 8.57 (dd, J = 4.7, 1.1 Hz, 1H), 7.89 (d, J = 7.6 Hz, 2H), 7.78 (t, J = 7.8 Hz), 1H), 7.1, J = 1.66 (dd 7.54 (d, J = 7.9 Hz, 2H), 7.48 (dd, J = 8.1, 4.7 Hz, 1H), 7.39 (s, 2H), 7.03 (t, J = 7.6 Hz, 2H), 6,87 (t, J = 7.8 Hz (2H), 1, 6 2H), 3.15 (dt, J = 13.8, 6.9 Hz, 1H), 2.59 - 2.45 (m, 4H), 1.46 (d, J = 6.9 Hz, 6H), 1.34 (t, J = 6.6 Hz, J, 16H. 1). 13 C NMR (126 MHz, CD2Cl2) δ / ppm 188.61, 152.72, 149.71, 147.44, 147.34, 147.05, 147.02, 131.61, 131,1283.4, 1 124.88, 124.01, 123.91, 123.13, 121.08, 120.45, 119.52, 116.29, 113.80, 35.14, 29.82, 24.31, 24.05.

[0156] Au5: 1H NMR (500 MHz, アセトン-d6) δ / ppm 8.77 (s, 2H), 8.16 (s, 1H), 8.04 (d, J = 5.1 Hz, 1H), 8.00 (d, J = 7.8 Hz), J = 7.8 Hz, = 1 2H), 7.81 (d, J = 5.0 Hz, 1H), 7.68 (d, J = 7.9 Hz, 4H), 7.16 (t, J = 7.6 Hz, 1H), 6.94 (t, J = 7.2 Hz, 1H), Jt 2, 8, 1.0 (d, 1H). J = 13.7, 6.8 Hz, 4H), 1.39 (d, J = 6.9 Hz, 12H), 1.18 (d, J = 6.8 Hz, 12H). 13 C NMR (126 MHz, アセトン-d6) δ / ppm 190.94, 151.06, 148.05, 146.42, 129.14, 126.83, 125.70, 123.10, 121.65, 117.91, 115.57, 114.42, 24.73, 24.32.

[0157] Au6: 1 H NMR (500 MHz, アセトン-d6) δ / ppm 8.80 (s, 2H), 8.51 (s, 2H), 7.93 (t, J = 7.8 Hz, 2H), 7.71 (d, J = 7.8. Hz ( 5 Hz), J = 4. 4 2H), 6.73 (d, J = 8.5 Hz, 2H), 2.69 (dt, J = 13.7, 6.9 Hz, 4H), 1.36 (d, J = 6.8 Hz, 12H), 1.18 (d, J = 6.8 Hz, 12H). 13C NMR (126 MHz, CD2Cl2) δ / ppm 189.43, 151.88, 146.95, 141.89, 140.12, 131.70, 130.40, 128.06, 124.97, 124.83, 123.23, 120.89, 114.51, 99.90, 29.60, 24.06, 23.73.

[0158] Au7: 1 H NMR (500 MHz, アセトン-d6) δ / ppm 8.75 (s, 2H), 8.28 (s, 1H), 7.95-7.80 (m, 3H), 7.85-7.69 (m, 5H), 7.42 (d, J = 7.5 Hz, 1H), 7.24 (t, J = 7.5 Hz, 1H), 7.14 (t, J = 7.5 Hz, 1H), 6.98 (t, J = 8.0 Hz, 1H), 6.85 (t, J = 7.0 Hz, 1H), 6.65 (d, J = 8.0 Hz, 1H), 2.74-2.65 (m, 4H), 1.44 (s, 6H), 1.40 (d, J = 7.0 Hz, 12H), 1.18 (d, J = 7.0 Hz, 12H).

[0159] Au8: 1<h2 style=";text-align:left;direction:ltr">H NMR (500 MHz, アセトン-d6) δ / ppm 8.65 (dd, J = 4.7, 1.2 Hz, 1H), 8.00 (dd, J = 8.1, 1.2 Hz, 1H), 7.93 (d, J = 1.8 Hz, 2H), 7.82 (t, J = 7.8 Hz, 1H), 7.68 (dd, J = 8.1, 4.8 Hz, 1H), 7.63 (d, J = 7.9 Hz, 2H), 7.56 (s, 2H), 7.08 (dd, J = 8.5, 2.0 Hz, 2H), 6.66 (d, J = 8.5 Hz, 2H), 3.24 (dt, J = 13.8, 6.9 Hz,1H), 2.63 (tt, J = 13.7, 6.9 Hz, 4H), 1.50 (d, J = 6.9 Hz, 6H), 1.38 (t, J = 6.9 Hz, 12H), 1.35 (s, 18H), 1.21 (d, J = 6.9 Hz, 6H), 1.17 (d, J = 6.9 Hz, 6H).<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> 13 <h2 style=";text-align:left;direction:ltr"> C NMR (126 MHz, アセトン-d6) δ / ppm 189.11, 153.17, 148.99, 147.94, 147.77, 139.02, 132.48, 131.90, 130.26, 128.71, 125.33, 124.77, 123.72, 122.18, 122.01, 121.60, 115.81, 113.74, 35.52, 35.00, 32.67, 24.93, 24.66, 24.52, 24.42, 24.19.<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0160] <h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> Au9:<h2 style=";text-align:left;direction:ltr"> 1H NMR (500 MHz, Xin-d6) δ / ppm 8.66 (dd, J = 4.7, 1.1 Hz, 1H), 8.02 (dd, J = 8.1, 1.1 Hz, 1H), 7.91–7.81 (m, 2H), 7.70 (dd, J = 8.2, 4.7 Hz, 1H), 7.64 (d, J = 7.9 Hz, 2H), 7.61–7.53 (m, 3H), 7.02 (t, J = 7.2 Hz, 1H), 6.83 (t, J = 7.3 Hz, 1H), 6.81–6.76 (m, 1H), 6.73 (d, J = 8.2 Hz, 1H), 6.61 (dd, J = 8.8, 4.6 Hz, 1H), 3.23 (dq, J = 14.0, 7.0 Hz, 1H), 2.62 (tt, J = 13.6, 6.8 Hz, 4H), 1.49 (d, J = 6.9 Hz, 6H), 1.36 (dd, J = 11.9, 6.9 Hz, 12H), 1.19 (dd, J = 20.0, 6.9 Hz, 12H). 19 F NMR (471 MHz, X-d6) δ / ppm -129.97. 13 C NMR (126 MHz, ΄-d6) δ / ppm 188.42; 132.47, 131.96, 130.17, 128.69, 125.39, 124.98, 124.80, 124.72, 124.65, 124.61, 116.86, 114.58, 114.52, 114.45, 111.85, 111.65, 105.07, 104.88, 35.48, 24.91;

[0161] Scheme 5 shows the synthesis of metal carbene complexes (Cu9, Cu10, and Cu11 (with π-extended pyrazine-fused NHC ligands)). [ka]

[0162] Cu9: 1 H NMR (500 MHz, acetone-d6) δ / ppm 8.23 ​​(dd, J = 6.5, 3.5 Hz, 2H), 8.00-7.96 (m, 2H), 7.95 (t, J = 7.9 Hz, 2H), 7.82 (d, J = 7.6 Hz, 2H), 7.74 (d, J = 7.9 Hz, 4H), 6.96-6.90 (m, 2H), 6.83-6.77 (m, 2H), 6.28 (d, J = 8.1 Hz, 2H), 2.86 (dt, J = 13.7, 6.8 Hz, 4H), 1.30 (d, J = 6.9 Hz, 12H), 1.19 (d, J = 6.8 Hz, 12H).

[0163] Cu10: 1 H NMR (500 MHz, CD2Cl2) δ / ppm 8.27 (dd, J = 6.5, 3.5 Hz, 2H), 7.95-7.86 (m, 4H), 7.80 (d, J = 7.6 Hz, 1H), 7.64 (d, J = 7.9 Hz, 4H), 7.50 (dd, J = 9.5, 2.5 Hz, 1H), 6.99 (t, J = 7.1 Hz, 1H), 6.85 (t, J = 7.3 Hz, 1H), 6.77-6.71 (m, 1H), 6.23 (d, J = 8.1 Hz, 1H), 6.09 (dd, J = 8.8, 4.5 Hz, 1H), 2.60 (dt, J = 13.6, 6.7 Hz, 4H), 1.27 (d, J = 6.9 Hz, 12H), 1.19 (d, J = 6.8 Hz, 12H).

[0164] Cu11: 1 H NMR (500 MHz, CD2Cl2) δ / ppm 8.26 (dd, J = 6.4, 3.5 Hz, 2H), 7.93-7.85 (m, 4H), 7.68-7.59 (m, 4H), 6.79 (d, J =7.6 Hz, 2H), 6.09 (d, J = 8.2 Hz, 2H), 2.60 (dt, J = 13.6, 6.8 Hz, 4H), 1.27 (d, J = 6.8 Hz, 12H), 1.19 (d, J = 6.8 Hz, 12H).

[0165] Scheme 6 shows the synthesis of metal carbene complexes (or metal carbene precursors or metal carbene complexes) Au10 and Au11 (with π-extended pyrazine fused NHC ligands (or π-extended pyrazine fused NHC ligands)). [ka]

[0166] Au10: 1 H NMR (500 MHz, CD2Cl2) δ / ppm 8.26 (dd, J = 6.4, 3.5 Hz, 1H), 7.89 (ddd, J = 20.1, 11.2, 5.6 Hz, 3H), 7.62 (d, J = 7.9 Hz, 2H), 7.06 (t, J = 7.4 Hz, 1H), 6.90 (t, J = 7.3 Hz, 1H), 6.61 (d, J = 8.1 Hz, 1H), 2.60 (dt, J = 13.6, 6.8 Hz, 2H), 1.36 (d, J = 6.8 Hz, 7H), 1.18 (d, J = 6.8Hz, 7H). 13C NMR (126 MHz, CD2Cl2) δ / ppm 198.43, 149.76, 147.78, 141.36, 140.88, 132.14, 131.37, 130.90, 129.76, 125.44, 124.37, 124.20, 119.75, 116.87, 113.97, 30.25, 24.61, 24.42.

[0167] Au11: 1 H NMR (400 MHz, CD2Cl2) δ / ppm 8.26 (dd, J = 6.5, 3.5 Hz, 2H), 7.94-7.83 (m, 6H), 7.62 (d, J = 7.9 Hz, 4H), 7.12 (dd, J = 8.5, 1.8 Hz, 2H), 6.53 (d, J = 8.5 Hz, 2H), 2.60 (dt, J = 13.7, 6.8 Hz, 4H), 1.38 (s, 18H), 1.37 (d, J = 7.0 Hz, 12H), 1.18 (d, J = 6.8 Hz, 12H). 13 C NMR (101 MHz, CD2Cl2) δ / ppm 198.71, 148.28, 147.74, 141.33, 140.94, 139.53, 132.12, 131.38, 130.82, 129.73, 125.41, 124.16, 121.96, 115.67, 113.26, 34.91, 32.50, 30.24, 24.66, 24.42.

[0168] The structures of Cu7 to Cu11 and Au5 to Au11 are shown below. [ka] [ka]

[0169] (result) The results of this instant work are shown below. Maximum emission wavelength (λ em ), emission lifetime (τ em ), emission quantum yield (or emission quantum yield) (Φ em ), radiative decay rate (or radiative decay rate) (k r ) and the non-radiative decay rate (k nr ) the photophysical properties of the complex can be evaluated. In thin films of degassed toluene and MCP (1,3-bis(N-carbazolyl)benzene), the Φ em Values ​​were determined directly by absolute measurement (using a Hamamatsu C11347 Quantaurus-QY Absolute PL quantum yield spectrometer (PL stands for photoluminescence)). Maximum emission wavelength (λ em ) is read from the emission spectrum. The emission lifetime (τ em ) measurements were carried out. The intensity of the luminescence decay (or emission decay) was monitored as a function of time.

number

[0170] Emission lifetimes were determined by fitting exponential decays using Origin software. Using the following equation, k of the complex r and k nr can be calculated respectively. k r = Φ em / τ em k nr = (1-Φ em ) / τ em

[0171] Photophysical characterization of compounds

[0172] [Table 1-1]

[0173] [Table 1-2]

[0174] [Table 2]

[0175] [Table 3]

[0176] [Table 4]

[0177] [Table 5]

[0178]

Table 6

[0179]

Table 7

[0180]

Table 8

[0181]

Table 9

[0182]

Table 10

[0183]

Table 11

[0184]

Table 12

[0185]

Table 13

[0186]

Table 14

[0187]

Table 15

[0188]

Table 16

[0189]

Table 17

[0190]

Table 18

[0191]

Table 19

[0192]

Table 20

[0193]

Table 21

[0194]

Table 22

[0195]

Table 23

[0196]

Table 24

[0197]

Table 25

[0198] [Table 26]

[0199] [Table 27]

[0200] [Table 28]

[0201] [Table 29]

[0202] [Table 30]

[0203] [Table 31]

[0204] Unless otherwise defined (or defined), all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosed invention belongs. The publications mentioned and materials cited in this disclosure are specifically incorporated by reference. Furthermore, unless otherwise stated, use of the expression "wt% (or weight %)" means "wt / wt% (weight / weight %)."

[0205] 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 (or equivalents) are intended to be encompassed in the scope of the appended claims.

Claims

1. Structure of Formula I: 【Chemistry 1】 Formula I A compound having the formula: The compound has an overall neutral, negative or positive charge, M is copper, silver or gold, the oxidation state of which is 0, +1, +2 or +3, preferably +1; P' has the structure of formula I' below: 【Chemistry 2】 Formula I' D is carbon; T, J and W are independently carbon or nitrogen, at least one of T, J and W is nitrogen, and when T is carbon, J is nitrogen, or when T is nitrogen, J is carbon, and T, J and W are bonded to one or no hydrogen atoms according to valence; X and Y are independently carbon or nitrogen, at least one of X and Y is nitrogen, and X and Y are bonded to one or no hydrogen atoms according to valency; R １ and R ２ are independently 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 ３ -C ２０ Cycloalkyl, unsubstituted C ３ -C ２０ Cycloalkyl, substituted C ２ -C ２０ Heterocyclyl, unsubstituted C ２ -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 cycloalkynyl or R １ , J., D. and R. ２ taken together form an unsubstituted aryl, a substituted aryl, an unsubstituted heteroaryl or a substituted heteroaryl; R ３ and R ４ are independently hydrogen, 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 ３ -C ２０ Cycloalkyl, unsubstituted C ３ -C ２０ Cycloalkyl, substituted C ２ -C ２０ Heterocyclyl, unsubstituted C ２ -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 is cycloalkynyl, R ３ ' and R ４ ' 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 ３ -C ２０ Cycloalkyl, unsubstituted C ３ -C ２０ Cycloalkyl, substituted C ２ -C ２０ Heterocyclyl, unsubstituted C ２ -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 is cycloalkynyl, Z is a substituted heteroaryl, an unsubstituted heteroaryl, a substituted polyheteroaryl, an unsubstituted polyheteroaryl, a substituted polyheterocyclyl, an unsubstituted polyheterocyclyl, a substituted or unsubstituted heterocyclyl, or -NR ａ R ｂ Wherein R ａ and R ｂ are independently hydrogen, substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C ３ -C ２０ Cycloalkyl, unsubstituted C ３ -C ２０ cycloalkyl, substituted heterocyclyl, unsubstituted heterocyclyl, substituted alkyl or unsubstituted alkyl; (i) R ３ and R ４ are not 3,5-dialkyl substituted aryl, (ii) R ３ and R ４ are not 3,5-dialkyl substituted phenyl, (iii) R ３ and R ４ are not 3,5-dimethylphenyl, (iv) R ３ and R ４ are not both 3,5-dimethylphenyl when M is Cu or Au; or (v) the compound is 【Chemistry 3】 or 【Chemistry 4】 Not a compound.

2. Structure of Formula II: 【Chemistry 5】 Formula II [In the formula, CY1 and CY2 are independently selected from substituted aryl, unsubstituted aryl, substituted polyaryl, unsubstituted polyaryl, substituted heteroaryl, unsubstituted heteroaryl, substituted polyheteroaryl, unsubstituted polyheteroaryl, substituted C ３ -C ２０ Cycloalkyl, unsubstituted C ３ -C ２０ Cycloalkyl, substituted C ３ -C ２０ Cycloalkenyl, unsubstituted C ３ -C ２０ Cycloalkenyl, substituted C ３ -C ２０ Cycloalkynyl or unsubstituted C ３ -C ２０ is cycloalkynyl.

2. The compound of claim 1 having the formula:

3. R ３ ' and R ４ 3. The compound of claim 1 or 2, wherein:

4. 4. The compound of claim 2 or 3, wherein CY1 and CY2 are independently substituted aryl, unsubstituted aryl, substituted polyaryl or unsubstituted polyaryl.

5. The compound according to any one of claims 2 to 4, wherein CY1 and CY2 are substituted aryl.

6. Structure of Formula III: 【Chemistry 6】 Formula III [In the formula, R ５ and R ６ is independently substituted or unsubstituted alkyl; n1 and n2 are independently an integer from 0 to 5, 1 to 5, 3 to 5 (e.g., 3); or an integer from 2 to 5 (e.g., 2). The compound according to any one of claims 1 to 5, having the formula:

7. Structure of Formula IV: 【Chemistry 7】 Formula IV [In the formula, n1 and n2 are independently an integer from 1 to 5, 2 to 5, or 3 to 5; L is absent, a single bond, a substituted alkyl, -(CH ２ ) ｎｘ -, oxygen, sulfur, or NRx, where nx is an integer from 1 to 3 (e.g., 1, 2, or 3) and Rx is unsubstituted alkyl, substituted alkyl, unsubstituted aryl, or substituted aryl; CY3 and CY4 are independently unsubstituted aryl, substituted aryl, unsubstituted polyaryl, substituted polyaryl, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted polyheteroaryl, substituted polyheteroaryl, unsubstituted C ３ -C ２０ Cycloalkyl, substituted C ３ -C ２０ Cycloalkyl, 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 fused combination thereof. The compound according to any one of claims 1 to 6, having the formula:

8. Structure of Formula V: 【Chemistry 8】 Formula V [In the formula, Each Ra is independently hydrogen, unsubstituted alkyl, or substituted alkyl; Each Rb is independently unsubstituted or substituted alkyl; L is absent, a single bond, a substituted alkyl, -(CH ２ ) ｎｘ -, oxygen, sulfur, or NRx, where nx is an integer from 1 to 3 (e.g., 1, 2, or 3) and Rx is unsubstituted alkyl, substituted alkyl, unsubstituted aryl, or substituted aryl; Optionally, at least one of X and Y is nitrogen. The compound according to any one of claims 1 to 7, having the formula:

9. (i) T is nitrogen, J is carbon and W is carbon; or (ii) T is nitrogen, J is carbon and W is nitrogen; or (iii) T is carbon, J is nitrogen and W is carbon; or (iv) T is carbon, J is nitrogen and W is nitrogen; The compound according to any one of claims 1 to 8.

10. Ra is independently hydrogen, unsubstituted alkyl or substituted alkyl; Rb is independently unsubstituted or substituted alkyl; 10. A compound according to claim 8 or 9.

11. P' is 【Chemistry 9】 [In the formula, Ra is independently hydrogen, unsubstituted alkyl or substituted alkyl; Rb is independently unsubstituted or substituted alkyl. Selected from: The compound according to any one of claims 1 to 10.

12. Ra is independently hydrogen, methyl, iso-propyl or -CH(C ２ H ５ ) ２ and Rb is independently methyl, isopropyl or —CH(C ２ H ５ ) ２ That is, The compound according to any one of claims 8 to 11.

13. CY3 and CY4 are independently selected from unsubstituted aryl, substituted aryl, unsubstituted polyaryl, substituted polyaryl, unsubstituted heteroaryl, substituted heteroaryl, substituted C ３ -C ２０ Cycloalkenyl, unsubstituted C ３ -C ２０ The compound according to any one of claims 7 to 12, which is a cycloalkenyl, or a fused combination thereof.

14. CY3 and CY4 are independently unsubstituted aryl, substituted aryl, unsubstituted heteroaryl, substituted heteroaryl, substituted C ３ -C ２０ Cycloalkenyl, unsubstituted C ３ -C ２０ The compound according to any one of claims 7 to 13, which is a cycloalkenyl, or a fused combination thereof.

15. Z has the following structure: 【Chemistry 10】 having X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ and X ８ are independently carbon or nitrogen; R ｘ１ , R ｘ２ , R ｘ３ , R ｘ４ , R ｘ５ , R ｘ６ , R ｘ７ and R ｘ８ are independently hydrogen, halogen, cyano, unsubstituted alkyl, substituted alkyl, unsubstituted alkoxy, substituted alkoxy, unsubstituted aryl, substituted aryl, unsubstituted heteroaryl or substituted heteroaryl; R ｘ１ , R ｘ２ , R ｘ３ , R ｘ４ , R ｘ５ , R ｘ６ , R ｘ７ Or R ｘ８ X corresponding to １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ Or X ８ is nitrogen, or R ｘ４ is a bond connecting to a substituent on L, or adjacent R groups taken together with the atoms on the ring to which they are attached independently represent a 5- or 6-membered substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C ３ -C ２０ Cycloalkenyl, unsubstituted C ３ -C ２０ cycloalkenyl, or when they form a fused combination (wherein in adjacent R groups, n is a consecutive pair of integers from 1 to 4 or 5 to 8), R ｘ１ , R ｘ２ , R ｘ３ , R ｘ４ , R ｘ５ , R ｘ６ , R ｘ７ Or R ｘ８ do not exist, L is absent, a single bond, a substituted alkyl, -(CH ２ ) ｎｘ -, oxygen, sulfur, or NRx, where nx is an integer from 1 to 3 (e.g., 1, 2, or 3) and Rx is unsubstituted alkyl, substituted alkyl, unsubstituted aryl, or substituted aryl; The compound according to any one of claims 1 to 14.

16. Z has the following structure: 【Chemistry 11】 having L' is substituted aryl, unsubstituted aryl, substituted heteroaryl or unsubstituted heteroaryl, preferably substituted aryl or unsubstituted aryl, preferably substituted phenyl or unsubstituted phenyl; The compound according to any one of claims 1 to 15.

17. Z has the following structure: 【Chemistry 12】 16. The compound of claim 15 having the formula:

18. R ｘ１ , R ｘ２ , R ｘ３ , R ｘ４ , R ｘ５ , R ｘ６ , R ｘ７ and R ｘ８ is independently hydrogen, halogen, methyl, cyano, trifluoromethyl, tert-butyl, methoxy, phenyl or pyridyl.

19. The compound according to any one of claims 1 to 18, wherein X and Y are nitrogen.

20. Structure of Formula VI': 【Chemistry 13】 Formula VI' , preferably Structure of Formula VI: 【Chemistry 14】 Formula VI [In the formula, V″ is carbon; U is carbon and V is nitrogen, or U is nitrogen and V is carbon, and U, V and V″ are bonded to one or no hydrogen atoms according to valence; Ra is hydrogen, unsubstituted alkyl or substituted alkyl; R ７ and R ８ are independently absent, hydrogen, substituted alkyl, unsubstituted alkyl, cyano, halogen, hydroxyl, thiol, nitro-, unsubstituted alkoxy, substituted alkoxy, unsubstituted aroxy, substituted aroxy, substituted aryl, unsubstituted aryl, or an adjacent R ７ group or adjacent R ８ The groups, taken together with the atoms in the ring to which they are attached, independently represent 5- or 6-membered substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C ３ -C ２０ Cycloalkenyl, unsubstituted C ３ -C ２０ cycloalkenyl, or a condensed combination thereof; n3 and n4 are independently an integer from 0 to 5, for example, 0, 1, 2, 3, 4, or 5.

2. The compound of claim 1 having the formula:

21. Structure of Formula VII': 【Chemistry 15】 Formula VII' , preferably Structure of Formula VII: 【Chemistry 16】 Formula VII [In the formula, Rv is absent, hydrogen, substituted alkyl or unsubstituted alkyl; R ７ and R ８ are independently hydrogen, substituted alkyl, unsubstituted alkyl, unsubstituted aryl, halogen, cyano, or Rv and R ７ are taken together with the atoms in the ring to which they are attached to form a 5- or 6-membered substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted C ３ -C ２０ Cycloalkenyl, unsubstituted C ３ -C ２０ cycloalkenyl, or a fused combination thereof.

21. The compound of claim 20 having the formula:

22. Rv is absent or hydrogen; R ７ and R ８ are independently hydrogen, iso-propyl, tert-butyl, phenyl, fluorine or cyano; or Rv and R ７ Together, 【Chemistry 17】 Forming 22. A compound according to claim 20 or 21.

23. R １ and R ２ are independently hydrogen, substituted alkyl, unsubstituted alkyl, substituted alkenyl, unsubstituted alkenyl, substituted alkynyl, unsubstituted alkynyl, substituted aryl, unsubstituted aryl; or R １ and R ２ taken together with the atoms in the ring to which they are attached form an unsubstituted aryl, a substituted aryl, an unsubstituted heteroaryl or a substituted heteroaryl; The compound according to any one of claims 20 to 22.

24. R １ and R ２ is hydrogen, or R １ and R ２ Taken together, they form the following structure: 【Chemistry 18】 The compound according to any one of claims 20 to 23, which forms

25. Structure of Formula VIII': 【Chemistry 19】 Formula VIII' , preferably Structure of Formula VIII: 【Chemistry 20】 Formula VIII having (ii) 6.6''2;26; ７ 22 ８ =2であり; (iii) 6.6''2;26; ７ 8;2 ８ 38であり; (iii) M=Cu(I); W=N; Ra=H; U=CH; V=V''=carbon; Rv=H; R ７ = R ８ = tert-butyl; (iv) M=Cu(I); W=N; Ra=H; U=CH; V=V''=carbon; Rv=H; R ７ = R ８ = phenyl; (v) M=Cu(I); W=N; Ra=H; U=CH; V=N; V''=carbon; Rv=not present; R ７ = R ８ = H; (vi) M=Cu(I); W=U=CH; V=V''=carbon; Rv=H; Ra=iso-propyl; R ７ = R ８ = H; (vii) M=Cu(I); W=N; Ra=H; U=CH; V=V''=carbon; R ８ = H; R and R ７ Together, 【Chemistry 21】 Forming (viii) M=Cu(I); W=U=CH; Ra=iso-propyl; V=V″=carbon; R ８ = H; R and R ７ Together, 【Chemical 22】 Forming ()) *_________________________________________________________ ７ __ ８ であり; x) 6.6''2;26; ７ 8;2 ８ =Fであり; (xi) M=Cu(I); W=N; Ra=H; U=CH; V=V''=carbon; Rv=H; R ７ = R ８ = methyl; (xii) M=Au(I); W=N; Ra=H; U=CH; V=carbon; Rv=H; V''=carbon; R ７ = R ８ = H; (xiii) M=Au(I); W=N; Ra=H; U=CH; V=carbon; Rv=H; V''=carbon; R ７ = H, R ８ = CN; (xiv) M=Au(I); W=N; Ra=H; U=N; V=carbon; Rv=H; V''=carbon; R ７ = R ８ = H; (xv) M=Au(I); W=U=CH; V=carbon; R=H; R=iso-propyl; V″=carbon; R ７ = R ８ = H; (xvi) M=Au(I); W=N; Ra=H; U=CH; V=N; Rv=absent; V''=carbon; R ７ = R ８ = H; (xvii) M=Au(I); W=N; Ra=H; U=CH; V=V''=carbon; Rv=H; R ７ = R ８ = CN; (xviii) M=Au(I); W=N; Ra=hydrogen; U=CH; V=V''=carbon; R ８ = H; R and R ７ Together, 【Chemistry 23】 Forming (xix) M=Au(I); W=U=CH; Ra=iso-propyl; V=V″=carbon; Rv=H; R ７ = R ８ = tert-butyl; (xx) M = Au(I); W = U = CH; Ra = iso-propyl; V = V'' = carbon; Rv = H; R ７ = H; R ８ = F; (xxi) M=Au(I); W=N; U=CH; Ra=H; V=V''=carbon; Rv=H; R ７ = R ８ = H; (xxii) M=Au(I); W=N; U=CH; Ra=H; V=V''=carbon; Rv=H; R ７ = R ８ = tert-butyl; () *_______________________________________________________ ７ __ ８ であり; For (i), (ii), (iii), (iv), (v), (vi), (vii), (viii), (xii), (xiii), (xiv), (xv), (xvi), (xvii), (xviii), (xix), (xx), and (xxiii), the dashed line indicates an absent bond; For (ix), (x), (xi), (xxi) and (xxii), the dashed line indicates the presence of a bond; 25. The compound of claim 24.

26. The structure: 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 wherein M=Cu(I), Au(I) or Ag(I).

2. The compound of claim 1 having the formula:

27. Substituted means halogen, hydroxyl, thiol, nitro-, unsubstituted alkyl, unsubstituted alkenyl, unsubstituted alkynyl, unsubstituted aryl, unsubstituted heteroaryl, unsubstituted arylalkyl, unsubstituted alkoxy, unsubstituted aroxy, unsubstituted alkylthio, unsubstituted arylthio, cyano, isocyano, unsubstituted carbonyl, unsubstituted carboxyl, oxo, unsubstituted amino, unsubstituted amido, unsubstituted sulfonyl, unsubstituted sulfonic acid, unsubstituted phosphoryl, unsubstituted phosphonyl, unsubstituted polyaryl or unsubstituted C ３ -C ２０ A compound according to any one of claims 1 to 25, which is meant to be substituted with one or more substituents selected from cycloalkyl and unsubstituted heterocyclyl.

28. An organic electronic component comprising a compound according to any one of claims 1 to 27.

29. 29. The organic electronic component of claim 28, wherein the organic electronic component is an organic light emitting diode (OLED) or an electrochemical light emitting cell (LEEC).

30. 30. The organic electronic component according to claim 28 or 29, wherein the compound is comprised in an emissive layer.

31. An anode; A cathode; a hole transport region; and Electron transport region and and the hole transport region comprises a hole injection layer and / or a hole transport layer, and optionally further comprises an electron blocking layer; the electron transport region comprises an electron transport layer and / or an electron injection layer, and optionally a 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; The organic electronic component according to any one of claims 28 to 30.

32. 31. The organic electronic component according to claim 29 or 30, wherein the light-emitting layer is formed by vacuum deposition, spin coating or ink printing (e.g. ink-jet printing or roll-to-roll printing).

33. A light-emitting layer comprising the compound according to any one of claims 1 to 27.

34. 28. An emissive layer comprising a compound according to any one of claims 1 to 27 and a pure organic emitter, wherein the compound acts as a sensitizer for transferring energy (e.g. exciton energy or photon energy) to the pure organic emitter.

35. 28. An emissive layer comprising a compound according to any one of claims 1 to 27 and a pure organic emitter, said compound having a higher singlet state than said pure organic emitter.

36. 28. An emissive layer comprising the compound according to any one of claims 1 to 27 and a pure organic emitter, wherein the compound acts as a sensitizer to transfer energy (e.g., exciton energy or photon energy) to the pure organic emitter, and the emitter exhibits thermally activated delayed fluorescence.

37. 28. An emissive layer comprising a compound according to any one of claims 1 to 27 and a pure organic emitter, said compound acting as a sensitizer for transferring energy (e.g. exciton energy or photon energy) to said pure organic emitter, said emitter being a boron-based emitter.

38. An OLED comprising a light-emitting layer according to any one of claims 33 to 37.

39. 40. A device comprising the OLED of claim 38 selected from a stationary visual display unit, a mobile visual display unit, an illumination unit, a keyboard, a clothing, an ornament, a garment accessory, a wearable device, a medical monitoring device, wallpaper, a tablet computer, a laptop, an advertising panel, a panel display unit, a household appliance or an office appliance.

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