Cerium-ethylenediamine ketone and cerium-salen type composites and their use in organic electronics.

Abstract

The present invention relates to electronically doped semiconductor materials and electronic components comprising cerium-ethylenediamine ketone-type and cerium-salen-type composites. The present invention also relates to the use of the cerium-ethylenediamine ketone-type and cerium-salen-type composites as electron acceptors, particularly as p-dopants and electron transport materials in organic electronic components. Furthermore, the present invention relates to novel cerium-ethylenediamine ketone-type and cerium-salen-type composites.

Description

[Technical Field]

[0001] The present invention relates to electronically doped semiconductor materials and electronic components including cerium-ethylenediamine ketone and cerium-salen complexes. The present invention also relates to the use of these cerium-ethylenediamine ketone and cerium-salen complexes as electron acceptors, particularly as p-dopants and electron transport materials in organic electronic components. Furthermore, the present invention relates to novel cerium-ethylenediamine ketone and cerium-salen complexes. [Background technology]

[0002] Organic electronics focuses on the development, characterization, and application of novel materials based on both organic small molecules and polymers that possess specific electronic properties necessary for the production of electronic components. These include, for example, organic field-effect transistors (OFETs) such as organic thin-film transistors (OTFTs), organic electroluminescent devices such as organic light-emitting diodes (OLEDs), organic solar cells (OSCs) such as exciton solar cells, dye-sensitized solar cells (DSSCs), or perovskite solar cells, photoconductive materials in organic photoconductors (OPCs), organic optical detectors, organic photoreceptors, light-emitting electrochemical cells (LECs), and electrophotography such as organic laser diodes.

[0003] As is well known, the electrical conductivity of organic semiconductor matrices can be greatly affected by doping. Such organic semiconductor matrix materials can be formed from either compounds with good electron-donating properties (p-conductors) or compounds with good electron-accepting properties (n-conductors). In contrast to inorganic semiconductors, organic semiconductors have very low intrinsic charge carrier concentrations. Therefore, organic semiconductor matrix materials are usually doped to achieve good semiconductor properties. In the case of n-doping, a strong electron donor (n-dopant) is used. This transfers electrons to the LUMO of the semiconductor matrix (n-doped), creating free electrons on the matrix (SOMO). In the case of p-doping, a strong electron acceptor (p-dopant) is used. This removes electrons from the HOMO of the semiconductor matrix (p-doped), creating a vacancy. In other words, in the case of p-doping, the LUMO of the dopant must be lower than the HOMO energy of the matrix. The dopant acts as an acceptor, leaving a mobile vacancy (SOMO) in the matrix.

[0004] p-dopant, known as electron-donating material, is an electron acceptor such as tetracyanoquinonemethane (TCNQ), 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinonemethane (F4TCNQ), trinaphthylenes (HATNA), metal oxides such as MoO3 and WO3, or radialene compounds as described in EP 2180029. These acceptor molecules create so-called vacancies in the semiconductor matrix material (vacancy transport material) through an electron transfer process. The conductivity of the semiconductor matrix material (vacancy transport material) then changes somewhat depending on the number and mobility of the vacancies.

[0005] However, the aforementioned compounds or compounds have drawbacks in their technical use in the manufacture of doped semiconductors or electronic components having corresponding doped layers. For example, the aforementioned compounds or compounds are too volatile, have too high an absorption coefficient, have unstable evaporation rates, and / or have poor thermal stability. In addition, some of these compounds are very expensive to manufacture.

[0006] Therefore, there remains a demand for compounds that are readily available or can be produced, are suitable for doping electron donor materials, and do not have the aforementioned drawbacks.

[0007] Only a few cerium-ethylenediamine ketone complexes are known, and no cerium-salen (cerium-bis(salicylidene)ethylenediamine) complexes are known. Several cerium-(IV) complexes are described in the literature. Reference J. Schlafer et al, Inorg. Chem, 2016, 55, 5422-5429 describes homopreptic cerium(IV) complexes having the following ligands: N,N'-bis(4,4,4,-trifluorobuto-1-en-3-one)-ethylenediamine, N,N'-bis(4,4,5,5-pentafluoropento-1-en-3-one)-ethylenediamine, N,N'-bis(4,4,5,5,6,6-heptafluorohex-1-en-3-one)-ethylenediamine, and N,N'-bis(4,4,4,-trifluorobuto-1-en-3-one)-propylenediamine.

[0008] The following homopreptic cerium(IV) complexes are described in the reference DW Wester et al., Inorg, Chem. 1985, 24, 4435-4437: JPEG0007870555000001.jpg160127.

[0009] NK Dutt et al. described the synthesis of rare-earth ethylenediamine bis-acetylacetone complexes (Chemistry of Rare-Earth Lanthanone-XIX Ethylenediamine Bis-Acetylacetone Complexes, J. Inorg. Nucl. Chem., 1968, Vol. 30, pp. 3273 - 3280). Among other Ce(III) complexes, [Ce(ethylenediamine-bis-acetylacetone)Cl3] and [Ce(ethylenediamine-bis-acetylacetone)NO3] are mentioned. In these complexes, the ligand is neutral and therefore uncharged. According to the present invention, the ligand is doubly negatively charged.

[0010] V. Balasubramanian et al. describe the synthesis of lanthanide(III) chelate complexes (Synthesis and Reactivity of Tetradentate Schiff Base Chelates of Lanthanide(III) Ions, Asian Journal of Chemistry 2003, Vol. 15, No. 1, pp. 139 - 143). The Ce(III) complexes mentioned include [Ce(ethylenediamine-bis-acylacetone)Cl3] and [Ce(ethylenediamine-bis-acylacetone-α-naphthyl isocyanate))Cl3] (where the ethylenediamine-bis-acylacetone ligand is in the keto form). In these complexes, the ligand is neutral and therefore uncharged. According to the present invention, the ligand is doubly negatively charged.

[0011] JH Timmons describes the cerium(IV) complex (bis[1,1,1,12,12,12-hexafluoro-2,11-bis(trifluoromethyl)-4,9-dimethyl-2,11-diolato-5,8-diazadodeca-4,8-diene(2-)]cerium(IV) CeC 28 H 28 F 24Template synthesis, crystals, and molecular structure of the O4N4, 8-coordinate cerium(IV) fluorinated Schiff base complex (Inorg. Chem. 1980, Vol. 19, No. 12, pp. 3553-3557). The ligands of the complex have different atomic connections. In other words, the ligands are not based on an acetylacetone structure.

[0012] International Publication No. 2021 / 048044 describes p-dostats as electron acceptors, specifically for use in organic electronic devices, and cerium(IV) diketonate complexes as electron transport materials.

[0013] Conventionally, the use of cerium(IV) ethylenediamine ketone type and / or cerium(IV) salen type and / or cerium(IV) bis(salicylidene)ethylenediamine type composites (hereinafter also referred to as cerium(IV) composites) as organic semiconductor materials was not known. In particular, the use of such cerium(IV) composites as p-dopants, electron transport materials, or electron acceptors has not yet been described.

[0014] Surprisingly, it has now been found that cerium(IV) composites can be advantageously used as p-dopants. Furthermore, it has been found that cerium(IV) composites can be used as electron transfer materials (ETMs) in organic electronic components such as organic light-emitting diodes (OLEDs), photovoltaics, organic solar cells (OPVs), organic diodes, or organic transistors.

[0015] Furthermore, many cerium(IV) diketonates evaporate very well under vacuum and sometimes exhibit high thermal stability. Therefore, they are essentially suitable for both variations of processing organic electronic components: vacuum coating (deposition) and solvent-based processing (solution processing). Summary of the present invention

[0016] The first object of the present invention is an electronic component comprising at least one compound of general formula (I), Ce 4+ [L1L2]4- (I) In the formula, L1 and L2 are each a ligand of formula (I.1) JPEG0007870555000002.jpg5886 are four-coordinate ligands independently selected from, where X independently represents O or S for each; Z is a bridging group having 2 or 3 carbon atoms between nitrogen atoms, where the carbon atoms are each unsubstituted or have 1, 2, 3, 4, 5, or 6 identical or different free radicals R 12 and are substituted, where two adjacent carbon atoms may be linked to each other by a double bond, or 2 or 3 of the carbon atoms are part of a mononuclear, binuclear, or trinuclear C6-C 14 aromatic or heteroaromatic ring system, where the heteroaromatic ring system has 4 to 13 carbon atoms and has 1, 2, or 3 identical or different heteroatoms or groups containing heteroatoms as ring members selected from N, NR 8 , O, S, SO, and SO2, where the aromatic or heteroaromatic ring system is unsubstituted or has 1, 2, 3, 4, or 5 identical or different free radicals R 9 and is substituted; A and B independently represent N or CR 7 ; R 1 and R 6 are independently selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C7 cycloalkyl, where C3-C7 cycloalkyl is unsubstituted or has 1, 2, 3, 4, 5, or 6 identical or different free radicals R 11 , C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b , C6-C having 4 to 13 carbon atoms 14 aryl and hetaryl, where hetaryl is N, NR 8The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 9 Replaced by; or, R 1 And A, along with the carbon atoms to which they are bonded, C6-C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 The ring members selected from O, S, SO, and SO2 have one, two, or three identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have one, two, three, or four identical or different free groups R 9 Replaced by, or R 6 And B, along with the carbon atoms to which they are bonded, C6-C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 The ring members selected from O, S, SO, and SO2 have one, two, or three identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have one, two, three, or four identical or different free groups R 9 Replaced by; R 2 and R 5 However, the free radicals are independently selected from hydrogen, CN, C1-C6 alkyl, C1-C6-haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, and C3-C7 cycloalkyl, where the C3-C7-cycloalkyl is unsubstituted or has 1, 2, 3, 4, 5, or 6 identical or different free radicals R 11 , C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b , C6-C having 4 to 13 carbon atoms 14 Replaced with aryl and hetalir, where hetalir is N, NR 8The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 9 Replaced by; R 2 And A, along with the carbon atoms to which they are bonded, C6-C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 The ring members selected from O, S, SO, and SO2 have one, two, or three identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have one, two, three, or four identical or different free groups R 9 Replaced by, or R 5 And B, along with the carbon atoms to which they are bonded, C6-C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 The ring members selected from O, S, SO, and SO2 have one, two, or three identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have one, two, three, or four identical or different free groups R 9 Replaced by; R 4a R 4b However, independently of each other, hydrogen, C1-C6 alkyl, and C6-C 14 Selected from aryl groups, where the aryl group is unsubstituted or consists of 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 7 However, hydrogen, CN, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b , C6-C having 4 to 13 carbon atoms14 Selected from aryl and hetalir, where hetalir is N, NR 8 The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 10 Replaced by; R 8 However, hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C6-C 14 Selected from aryls, where the aryl is unsubstituted or consists of 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 9 However, CN, halogen, C1-C6 alkyl, C1-C6 haloalkyl, and C6-C 14 Selected from aryl groups, where the aryl group is either unsubstituted or substituted with 1, 2, 3, 4, or 5 identical or different free radicals selected from C1-C4 alkyl and C1-C4 haloalkyl groups; R 10 However, these are selected from CN, halogen, C1-C4 alkyl, and C1-C4 haloalkyl; R 11 However, these are selected from CN, halogen, C1-C4 alkyl, and C1-C4 haloalkyl; R 12 However, the C3-C7 cycloalkyl group is independently selected from halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, and C3-C7 cycloalkyl groups, where the C3-C7 cycloalkyl group is either unsubstituted or has 1, 2, 3, 4, 5, or 6 identical or different free radicals R 11 , C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b , C6-C having 4 to 13 carbon atoms 14 Replaced with aryl and hetalir, where hetalir is N, NR 8The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 9 It will be replaced by this.

[0017] A further object of the present invention is an electronic component comprising at least one compound of general formula (I), Ce 4+ [L1L2] 4- (I) In the formula, L1 and L2 are ligands of formula (II), respectively. A tetradentate ligand independently selected from JPEG0007870555000003.jpg5074, in the formula, CR 3 Base and CR 4 Between JPEG0007870555000004.jpg617 represents a single bond or a double bond; X represents either O or S independently of each other; A and B are independent of each other and are N or CR 7 It represents; R 1 and R 6 However, hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b , C6-C having 4 to 13 carbon atoms 14 Selected independently from aryl and hetalir, where hetalir is N, NR 8 The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 9 Replaced by; or, R 1 And A, along with the carbon atoms to which they are bonded, C6-C14 forms an aryl group or a heteroaryl group having 4 to 13 carbon atoms, wherein the heteroaryl has, as ring members selected from N, NR 8 , O, S, SO, and SO2, 1, 2, or 3 identical or different heteroatoms or groups containing heteroatoms, and the aryl and heteroaryl are unsubstituted or substituted with 1, 2, 3, or 4 identical or different free radicals R 9 , or R 6 and B, together with the carbon atom to which they are attached, form a C6-C 14 aryl group or a heteroaryl group having 4 to 13 carbon atoms, wherein the heteroaryl has, as ring members selected from N, NR 8 , O, S, SO, and SO2, 1, 2, or 3 identical or different heteroatoms or groups containing heteroatoms, and the aryl and heteroaryl are unsubstituted or substituted with 1, 2, 3, or 4 identical or different free radicals R 9 ; R 3 and R 4 are independently selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R<http: / / www.wipo.int / standards / XMLSchema / ST36 / XMLSchema / 4b , C6-C having 4 to 13 carbon atoms 14 aryl and heteroaryl are independently selected, wherein the heteroaryl has, as ring members selected from N, NR 8 , O, S, SO, and SO2, 1, 2, or 3 identical or different heteroatoms or groups containing heteroatoms, and wherein the aryl and heteroaryl are unsubstituted or substituted with 1, 2, 3, 4, or 5 identical or different free radicals R 9 , or R 3 and R 4 together with the carbon atom to which they are attached, form a C6-C 14 aryl group or a heteroaryl group having 4 to 13 carbon atoms, wherein the heteroaryl has, as ring members selected from N, NR 8The ring members selected from O, S, SO, and SO2 have one, two, or three identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have one, two, three, or four identical or different free groups R 9 Replaced by; R 2 and R 5 However, hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b , C6-C having 4 to 13 carbon atoms 14 Selected independently from aryl and hetalir, where hetalir is N, NR 8 The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 9 Replaced by; R 4a R 4b However, independently of each other, hydrogen, C1-C6 alkyl, and C6-C 14 Selected from aryl groups, where the aryl group is unsubstituted or consists of 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 7 However, hydrogen, CN, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b , C6-C having 4 to 13 carbon atoms 14 Selected from aryl and hetalir, where hetalir is N, NR 8The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 10 Replaced by; R 8 However, hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C6-C 14 Selected from aryl groups; where the aryl group is unsubstituted or consists of 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 9 However, CN, halogen, C1-C6 alkyl, C1-C6 haloalkyl, and C6-C 14 Selected from aryl groups; where the aryl group is unsubstituted or substituted with 1, 2, 3, 4, or 5 identical or different free radicals selected from C1-C4 alkyl and C1-C4 haloalkyl groups; R 10 However, it is selected from CN, halogen, C1-C4 alkyl, and C1-C4 haloalkyl.

[0018] A further object of the present invention is a doped semiconductor matrix material comprising at least one electron donor and at least one compound of formula (I), where L1 and L2 are tetradentate ligands independently selected from ligands of formula (I.1) or formula (II), where X, Z, A, B, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 This is as defined above and below.

[0019] A further object of the present invention is a compound of formula (I) (wherein L1 and L2 are tetradentate ligands independently selected from ligands of formula (I.1) or formula (II), respectively, where X, Z, A, B, R 1 , R 2 , R 3 , R4 , R 5 , and R 6 (As defined above and below), — As an organic semiconductor, — As a doping agent in organic semiconductor matrix materials, particularly as a p-dopant in the vacancy transport layer, — As a charge injector in the charge injection layer, — As an electron transport layer, — As a cathode material in organic batteries, — As an electrochromic material, — As an electron acceptor It is for use.

[0020] A further object of the present invention is the use of Ce(III)-complex anions obtained by reduction of compound (I) as defined above and below, or charge transfer complexes of compound (I) and an electron donor as defined above and below, as organic conductors, in particular organic conductors, electrochromic materials, charge transfer complexes, or ferromagnetic materials.

[0021] A further object of the present invention is a compound of general formula (I), Ce 4+ [L1L2] 4- (I) These are charge transfer complexes, their reduced products, and mixtures thereof. In the formula, L1 and L2 are ligands of formula (I.1), respectively. A tetradentate ligand independently selected from JPEG0007870555000005.jpg5886, in the formula, X represents either O or S independently of each other; Z is a bridging group having two or three carbon atoms between nitrogen atoms, where each carbon atom is either unsubstituted or one, two, three, four, five, or six identical or different free groups R 12 Substituted, where two adjacent carbon atoms may be linked to each other by a double bond, or two or three of the carbon atoms may be mononuclear, dinuclear, or trinuclear C6-C 14It is part of an aromatic or heteroaromatic ring system, where the heteroaromatic ring system has 4 to 13 carbon atoms, and also contains N, NR 8 The aromatic or heteroaromatic ring system has one, two, or three identical or different heteroatoms or heteroatom-containing groups as ring members selected from O, S, SO, and SO2, wherein the aromatic or heteroaromatic ring system is either unsubstituted or has one, two, three, four, or five identical or different free groups R 9 Replaced by; A and B are independent of each other and are N or CR 7 It represents; R 1 and R 6 However, the free radicals are independently selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, and C3-C7 cycloalkyl, where the C3-C7 cycloalkyl is unsubstituted or has 1, 2, 3, 4, 5, or 6 identical or different free radicals R 11 , C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b , C6-C having 4 to 13 carbon atoms 14 Replaced with aryl and hetalir, where hetalir is N, NR 8 The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 9 Replaced by; or, R 1 And A, along with the carbon atoms to which they are bonded, C6-C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 The ring members selected from O, S, SO, and SO2 have one, two, or three identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have one, two, three, or four identical or different free groups R 9Replaced by, or R 6 And B, along with the carbon atoms to which they are bonded, C6-C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 The ring members selected from O, S, SO, and SO2 have one, two, or three identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have one, two, three, or four identical or different free groups R 9 Replaced by; R 2 and R 5 However, the free radicals are independently selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, and C3-C7 cycloalkyl, where the C3-C7 cycloalkyl is unsubstituted or has 1, 2, 3, 4, 5, or 6 identical or different free radicals R 11 , C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b , C6-C having 4 to 13 carbon atoms 14 Replaced with aryl and hetalir, where hetalir is N, NR 8 The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 9 Replaced by; R 2 And A, along with the carbon atoms to which they are bonded, C6-C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 The ring members selected from O, S, SO, and SO2 have one, two, or three identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have one, two, three, or four identical or different free groups R 9Replaced by, or R 5 And B, along with the carbon atoms to which they are bonded, C6-C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 The ring members selected from O, S, SO, and SO2 have one, two, or three identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have one, two, three, or four identical or different free groups R 9 Replaced by; R 4a R 4b However, independently of each other, hydrogen, C1-C6 alkyl, and C6-C 14 Selected from aryl groups, where the aryl group is unsubstituted or consists of 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 7 However, hydrogen, CN, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b , C6-C having 4 to 13 carbon atoms 14 Selected from aryl and hetalir, where hetalir is N, NR 8 The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 10 Replaced by; R 8 However, hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C6-C 14 Selected from aryls, where the aryl is unsubstituted or consists of 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 9However, CN, halogen, C1-C6 alkyl, C1-C6 haloalkyl, and C6-C 14 Selected from aryl groups, where the aryl group is either unsubstituted or substituted with 1, 2, 3, 4, or 5 identical or different free radicals selected from C1-C4 alkyl and C1-C4 haloalkyl groups; R 10 However, these are selected from CN, halogen, C1-C4 alkyl, and C1-C4 haloalkyl; R 11 However, these are selected from CN, halogen, C1-C4 alkyl, and C1-C4 haloalkyl; R 12 However, the C3-C7 cycloalkyl group is independently selected from halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, and C3-C7 cycloalkyl groups, where the C3-C7 cycloalkyl group is either unsubstituted or has 1, 2, 3, 4, 5, or 6 identical or different free radicals R 11 , C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b , C6-C having 4 to 13 carbon atoms 14 Replaced with aryl and hetalir, where hetalir is N, NR 8 The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 9 Replaced by; However, the following compounds are excluded: JPEG0007870555000006.jpg201129.

[0022] A further object of the present invention is a compound of general formula (I), Ce 4+ [L1L2] 4- (I) These are charge transfer complexes, their reduced products, and mixtures thereof. In the formula, L1 and L2 are ligands of formula (II), respectively. A tetradentate ligand independently selected from JPEG0007870555000007.jpg5074, in the formula, CR 3 Base and CR 4 Between JPEG0007870555000008.jpg617 represents a single bond or a double bond; X represents either O or S independently of each other; A and B are independent of each other and are N or CR 7 It represents; R 1 and R 6 However, hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b , C6-C having 4 to 13 carbon atoms 14 Selected independently from aryl and hetalir, where hetalir is N, NR 8 The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 9 Replaced by; or, R 1 And A, along with the carbon atoms to which they are bonded, C6-C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 The ring members selected from O, S, SO, and SO2 have one, two, or three identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have one, two, three, or four identical or different free groups R 9 Replaced by, or R 6 And B, along with the carbon atoms to which they are bonded, C6-C 14It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 The ring members selected from O, S, SO, and SO2 have one, two, or three identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have one, two, three, or four identical or different free groups R 9 Replaced by; R 3 and R 4 However, hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b , C6-C having 4 to 13 carbon atoms 14 Selected independently from aryl and hetalir, where hetalir is N, NR 8 The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 9 Replaced by, or R 3 and R 4 However, along with the carbon atoms to which they are bonded, C6-C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 The ring members selected from O, S, SO, and SO2 have one, two, or three identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have one, two, three, or four identical or different free groups R 9 Replaced by; R 2 and R 5 However, hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R4b , C6-C 14 Independently selected from aryls and hetalyrs having 4 to 13 carbon atoms, where the hetalyr is N, NR 8 The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 9 Replaced by; R 4a R 4b However, independently of each other, hydrogen, C1-C6 alkyl, and C6-C 14 Selected from aryl groups, where the aryl group is unsubstituted or consists of 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 7 However, hydrogen, CN, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b , C6-C 14 Selected from aryls and hetalyrs having 4 to 13 carbon atoms, where the hetalyr is N, NR 8 The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 10 Replaced by; R 8 However, hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C6-C 14 Selected from aryl groups; where aryl is unsubstituted or consists of 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 9 However, CN, halogen, C1-C6 alkyl, C1-C6 haloalkyl, and C6-C 14Selected from aryl groups; where the aryl group is unsubstituted or substituted with 1, 2, 3, 4, or 5 identical or different free radicals selected from C1-C4 alkyl and C1-C4 haloalkyl groups; R 10 However, it is selected from CN, halogen, C1-C4 alkyl, and C1-C4 haloalkyl. However, the compound of the following formula (I): L1 = L2 = N,N'-bis(4,4,4,-trifluorobuto-1-en-3-one)-ethylenediamine, L1 = L2 = N,N'-bis(4,4,5,5,5-pentafluoropento-1-en-3-one)-ethylenediamine, L1 = L2 = N,N'-bis(4,4,5,5,6,6,6-heptafluorohex-1-en-3-one)-ethylenediamine And their reaction products are excluded, as well as the following compounds: JPEG0007870555000009.jpg194138 and its reaction products are excluded.

[0023] The present invention has the following advantages. — All cerium-(IV)-composites according to the present invention have low production costs. — The cerium-(IV)-complex according to the present invention is advantageously suitable as an electron acceptor for use as a p-dopant, and as an electron transport material in organic electron components. — The cerium-(IV)-composite according to the present invention exhibits superior conductivity compared to known electron acceptors. — The cerium-(IV) composite according to the present invention exhibits improved thermal stability of the doped layer compared to the latest technology. Furthermore, the cerium-(IV)-compound according to the present invention is characterized by higher doping efficiency. — The cerium-(IV)-composite according to the present invention exhibits low absorption across all doped layers. Therefore, it can reduce or even prevent parasitic absorption and radiation. - The cerium-(IV)-complex according to the invention is suitable for the production of organic and hybrid optoelectronic components by both solvent treatment and vacuum reprocessing.

[0024] The terms cerium compound and cerium complex are used synonymously and are defined by formula (I). Ligands that do not have a metal atom (cerium atom) are defined by formula (II).

[0025] The term reduct of compound (I) is an anion complex, especially a Ce(III) anion complex, where the corresponding counterion is donated from the hole-conductive material (HTL) of the matrix. The semiconductor matrix material is defined below.

[0026] In the context of the present invention, [Ce(ac2en)Cl3], [Ce(enac)2Cl3], and [Ce(enac)2(NO3)3] are not reducts of compound (I), where ac2en and enac have the same meaning, in particular, ac2en is keto-type bis(acetylacetone)ethylenediamine, and enac is ethylenediamine-bis-acetylacetone.

[0027] The term charge transfer complex of compound (I) refers to the formation of an ion pair with the free cation of the matrix material (hole transport material, HTL).

[0028] In the context of the present invention, formula (II) represents an exemplary mesomeric structure, but the ligands L1 and L2 are not limited thereto. Other mesomeric structures are selected from formulas a, b, c, and d. JPEG0007870555000010.jpg140133The mesomeric structures a, b, c, and d apply equally to the ligands of formula (I.1). Preferably, L1 and L2 have the mesomeric structure of formula a.

[0029] In the context of the present invention, a four-coordinate ligand (also called tetradentate) is a ligand that binds to a metal atom (cerium atom) with four atoms.

[0030] In the context of the present invention, a homoleptic cerium(IV) compound is a complex (L1 = L2) in which all ligands are identical.

[0031] In the context of the present invention, a heteroleptic cerium(IV) compound is a complex (L1 ≠ L2) in which one ligand has a different meaning from the other ligand.

[0032] In the context of the present invention, the prefix C n -C m indicates the number of carbon atoms that a molecule or the residue specified thereby may contain.

[0033] In the context of the present invention, the expression "C1-C6 alkyl" refers to an unbranched or branched saturated hydrocarbon group having 1 to 6 carbon atoms. C1-C6 alkyl is, for example, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, or 1-ethyl-2-methylpropyl. C1-C4 alkyl refers to, for example, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, or 1,1-dimethylethyl.

[0034] In the context of the present invention, the expression "C1-C6 alkoxy" refers to a saturated C1-C6 alkyl group, defined above, that is bonded via one oxygen atom. An alkoxy group having 1 to 4 carbon atoms, particularly 1 or 2 carbon atoms, is preferred. C1-C2 alkoxys are methoxy or ethoxy. C1-C4 alkoxys are, for example, methoxy, ethoxy, n-propoxy, 1-methylethoxy (isopropoxy), butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy), or 1,1-dimethylethoxy (tert-butoxy). C1-C6 alkoxys include the meanings given to C1-C4 alkoxys, and further include, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexyloxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, and 3,3-dimethylbutoxy.

[0035] In the context of the present invention, the expression "C1-C6 alkylsulfanil" refers to a saturated C1-C6 alkyl group, defined above, that is bonded via one sulfur atom. Alkylsulfanil groups having 1 to 4 carbon atoms, particularly 1 or 2 carbon atoms, are preferred. C1-C2 alkylsulfanils are methylsulfanil or ethylsulfanil. C1-C4 alkylsulfanils are, for example, methylsulfanil, ethylsulfanil, n-propylsulfanil, 1-methylethylsulfanil (isopropylsulfanil), butylsulfanil, 1-methylpropylsulfanil (sec-butylsulfanil), 2-methylpropylsulfanil (isobutylsulfanil), or 1,1-dimethylethylsulfanil (tert-butylsulfanil). C1-C6 alkylthio includes the meaning given for C1-C4 alkylsulfanyl, and furthermore, for example, pentylsulfanyl, 1-methylbutylsulfanyl, 2-methylbutylsulfanyl, 3-methylbutylsulfanyl, 1,1-dimethylpropylsulfanyl, 1,2-dimethylpropylsulfanyl, 2,2-dimethylpropylsulfanyl, 1-ethylpropylsulfanyl, hexylsulfanyl, 1-methylpentylsulfanyl, 2-methylpentylsulfanyl, 3-methylpentylsulfanyl, 4-methyl These are lupentyl sulfanyl, 1,1-dimethylbutyl sulfanyl, 1,2-dimethylbutyl sulfanyl, 1,3-dimethylbutyl sulfanyl, 2,2-dimethylbutyl sulfanyl, 2,3-dimethylbutyl sulfanyl, 3,3-dimethylbutyl sulfanyl, 1-ethylbutyl sulfanyl, 2-ethylbutyl sulfanyl, 1,1,2-trimethylpropyl sulfanyl, 1,2,2-trimethylpropyl sulfanyl, 1-ethyl-1-methylpropyl sulfanyl, or 1-ethyl-2-methylpropyl sulfanyl.

[0036] In the context of this invention, the terms "haloalkyl," "haloalkoxy," and "haloalkyl-sulfanil" refer to partially or completely halogenated alkyl, alkoxy, or alkylsulfanil. In other words, one or more hydrogen atoms, for example, one, two, three, four, or five hydrogen atoms bonded to one or more carbon atoms of the alkyl, alkoxy, or alkylsulfanil, are substituted with halogen atoms, particularly fluorine or chlorine.

[0037] In the context of the present invention, the term "cycloalkyl" refers to a carbocyclic free radical, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and preferably a monocyclic free radical having 3 to 7 carbon atoms, such as cyclopentyl, cyclohexyl, and cycloheptyl, where the bonding of a molecule to the free radical can be done via any suitable carbon atom. In the case of substitution, these can generally have 1, 2, 3, 4, 5, or 6, preferably 1, 2, or 3, and particularly preferably 1, of the above-defined "substituents".

[0038] In the context of the present invention, the term "alkylene" refers to an alkanediyl group, i.e., a hydrocarbon crosslinking group having two or three carbon atoms, such as -(CH2)2-, -(CH2)3-, -CH2-CH-CH2-, etc. In the case of substitution, these generally consist of one, two, or three substituents R as defined above. 12 It can have.

[0039] In the context of this invention, the term "alkenylene" refers to monounsaturated or polyunsaturated alkylene groups having two or three carbon atoms, particularly monounsaturated analogs, such as -CH=CH-, -CH=CH-CH2-, -CH2-CH=CH-, etc. In the case of substitution, these generally have one, two, or three substituents R as defined above. 12 It can have.

[0040] In the context of the present invention, "mononuclear, dinuclear, or trinuclear C6-C 14The term “part of an aromatic or heteroaromatic ring system” refers to the corresponding double or multiple linked aryl or hetalil analogues.

[0041] In the context of the present invention, the expression "a bridging group having two or three carbon atoms between nitrogen atoms" corresponds to having two or three carbon atoms linearly between adjacent bonds (nitrogen atoms).

[0042] The term "halogen" refers to fluorine, chlorine, bromine, or iodine, respectively.

[0043] In the context of the present invention, the term "aryl" typically includes mononuclear or polynuclear free radicals of aromatic hydrocarbons having 6 to 14, preferably 6 to 10, carbon atoms. Examples of aryls include phenyl, naphthyl, indenyl, fluorenyl, anthracenyl, phenantrenyl, naphthacenyl, crisenyl, pyrenyl, and especially phenyl or naphthyl.

[0044] In the context of the present invention, the term "hetalil" includes a free group of a mononuclear or polynuclear aromatic hydrocarbon having 4 to 13 carbon atoms, wherein 1, 2, or 3 carbon atoms are substituted by 1, 2, or 3 identical or different heteroatoms or groups containing heteroatoms as ring members, and the heteroatoms and groups containing heteroatoms are N, NR 8The hetalil group is selected from O, S, SO, and SO2. The hetalil group may be bonded to the rest of the molecule via a ring carbon or ring nitrogen. Examples of five- or six-membered aromatic heterocycles (also called heteroaromatic rings or hetalils) are 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrzolyl, 4-pyrzolyl, 5-pyrzolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazole-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, and 2-pyrazinyl. Examples of 8-membered, 9-membered, or 10-membered aromatic heterobicyclic rings include hetalils having one of the aforementioned 5-membered or 6-membered heteroaromatic rings and another aromatic carbocyclic ring or a 5-membered or 6-membered heterocyclic ring fused thereto, such as condensed benzene, thiophene-, furan-, pyrrole-, pyrazole-, imidazole-, pyridine-, or pyrimidine-rings. These bicyclic hetalylenes include, for example, quinolinyl, isoquinolinyl, cinnolinyl, indolyl, indolidinyl, isoindolyl, indazolyl, benzofuryl, especially 2-benzofuryl, benzothienyl, especially 2-benzothienyl, benzo[b]thiazolyl, especially 2-benzo[b]thiazolyl, benzoxazolyl, especially 2-benzoxazolyl, benzothiazolyl, especially 2-benzothiazolyl, benzimidazolyl, especially 2-benzoimidazolyl, imidazo[1,2-a]pyridine-2-yl, thieno[3,2-b]pyridine-5-yl, imidazo-[2,1-b]-thiazole-6-yl, and 1,2,4-triazolo[1,5-a]pyridine-2-yl.

[0045] The notation "CN" represents a cyano group (-C≡N).

[0046] When a '#' appears in the formula, it indicates a preferred structure of the compound of the present invention, and it indicates a bond to the rest of the molecule.

[0047] Cerium compound of formula (I) Suitable cerium(IV) compounds in the meaning of the present invention are compounds of general formula (I) in which L1 and L2 have any of the meanings as defined above and below, Ce 4+ [L1L2] 4- (I) wherein, - L1 and L2 have the same meaning, - L1 and L2 have different meanings respectively, and - L1 and L2 are a mixture of two or more compounds of formula (I). Preferred are compounds of formula (I) in which L1 and L2 have the same meaning.

[0048] Homoleptic compounds of formula (I) are prepared by reaction of a ligand of formula (I.1) or formula (II) with a cerium salt. Usually, the cerium salt is soluble in the reaction medium. Suitable salts are cerium ammonium nitrate and cerium ammonium sulfate. The ligands can be used as commercially available products or prepared by synthesis known to those skilled in the art.

[0049] Heteroleptic compounds of formula (I) are - mixing two different homoleptic cerium compounds in a suitable solvent, - mixing a homoleptic cerium compound with a ligand different from the ligand of the cerium compound used or an alkali / alkaline earth salt thereof, - depositing two different homoleptic cerium compounds, - depositing a homoleptic cerium compound having a ligand different from the ligand of the cerium compound used (vapor co - condensation) by which they are prepared.

[0050] In the cerium compounds of formula (I), L1 and L2 are ligands of formula (I.1) or formula (II) A tetradentate ligand independently selected from JPEG0007870555000011.jpg5886 and JPEG0007870555000012.jpg5074, where, Free radicals X, Z, A, B, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 However, it has the meanings defined above and below.

[0051] In a preferred embodiment, Z is a C2-C3 alkylene or C2-C3 alkenylene, where the alkylene or alkenylene is unsubstituted or has 1, 2, 3, 4, 5, or 6 identical or different free groups R 12 Substituted with; or two or three carbon atoms of the bridging group are one or two C6-C6 groups. 10 It is part of an aromatic or heteroaromatic ring system, the heteroaromatic ring system having 4 to 13 carbon atoms, N, NR 8 The aromatic or heteroaromatic ring system has one, two, or three identical or different heteroatoms or heteroatom-containing groups as ring members selected from O, S, SO, and SO2, wherein the aromatic or heteroaromatic ring system is either unsubstituted or has one, two, three, four, or five identical or different free groups R 9 It is replaced by, here, R 12 and R 9 However, it is defined above and below.

[0052] Preferably, the cerium compound of formula (I) is such that ligands L1 and L2 are ligands of formula (II) that are independently selected.

[0053] The preferred option is R 1 , R 2 , R 5 , and R 6 Hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b, and ligands of formula (I.1) or (II) that are independently selected from base A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, and A19. JPEG0007870555000013.jpg201129 Here, # indicates a bond to a base of formula (I.1) or (II), where R A , R B , R C , R D , and R E but independently selected from hydrogen, CN, halogen, C1-C4 alkyl, and C1-C4 haloalkyl; or, R 1 And A, along with the carbon atoms to which they are bonded, C6-C 14 An aryl group is formed, where the aryl is unsubstituted or consists of 1, 2, 3, or 4 identical or different free groups R 9 Replaced by; or, R 6 And B, along with the carbon atoms to which they are bonded, C6-C 14 An aryl group is formed, where the aryl is unsubstituted or consists of 1, 2, 3, or 4 identical or different free groups R 9 Replaced by; R 4a and R 4b However, hydrogen, C1-C6 alkyl, and C6-C 14 A free group R is independently selected from the aryl group, where the aryl group is either unsubstituted or consists of 1, 2, 3, 4, or 5 identical or different free groups. 10 Replaced by; R 9 However, CN, halogen, C1-C6 alkyl, C1-C6 haloalkyl, and C6-C 14 Selected from aryl groups, where the aryl group is unsubstituted or substituted with 1, 2, 3, 4, or 5 identical or different free radicals selected from C1-C4 alkyl and C1-C4 haloalkyl groups; also, R 10However, it is selected from CN, halogen, C1-C4 alkyl, and C1-C4 haloalkyl. Regardless of their appearance, free group R A , R B , R C , R D , and R E However, it is preferably selected from hydrogen, CN, fluorine, chlorine, C1-C4 alkyl, C1-C4 fluoroalkyl, and C1-C4 chloroalkyl. Particularly preferred are free groups R, which are independently selected from hydrogen, CN, C1-C4 fluoroalkyl, fluorine, and chlorine. A , R B , R C , R D , and R E In particular, the free group R A , R B , R C , R D , and R E However, each element independently represents either hydrogen or CF3.

[0054] In one embodiment, in formula (I.1) or (II), R 1 , R 2 , R 5 , and R 6 This is independently selected from hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, and A1. JPEG0007870555000014.jpg5649# shows the bonding to the rest of the numerator of formula (II), where R A , R B , R C , R D , and R E However, it is independently selected from hydrogen, CN, fluorine, chlorine, C1-C4 alkyl, C1-C4 fluoroalkyl, and C1-C4 chloroalkyl, preferably selected from hydrogen, CN, fluorine, and chlorine; or, R 1 And A, together with the carbon atoms to which they are bonded, form a phenyl ring, where phenyl is unsubstituted or has 1, 2, 3, or 4 identical or different free groups R 9Replaced by; or, R 6 B and B, together with the carbon atoms to which they are bonded, form a phenyl ring, where phenyl is unsubstituted or has 1, 2, 3, or 4 identical or different free groups R 9 Replaced by; R 9 The substituent is selected from CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl, and phenyl, where phenyl is either unsubstituted or substituted with 1, 2, 3, 4, or 5 identical or different substituents selected from C1-C4 alkyl or C1-C4 haloalkyl.

[0055] In another embodiment, in formula (I.1) or (II), R 1 and R 6 It is selected independently from CF3 and A1, where R A , R B , R C , R D , and R E However, it is independently selected from CN, CF3, fluorine, and chlorine; R 2 and R 5 R is independently selected from hydrogen, CF3, and A1, where R A , R B , R C , R D , and R E However, it is independently selected from hydrogen, CN, CF3, fluorine, and chlorine; or, R 1 A and A, together with the carbon atoms to which they are bonded, form a phenyl ring, where phenyl is unsubstituted or has one or two identical or different free groups R 9 Replaced by; or, R 6 B and B, together with the carbon atoms to which they are bonded, form a phenyl ring, where phenyl is unsubstituted or has one or two identical or different free groups R 9 Replaced by; R 9The element is selected from CN, halogen, C1-C2 alkyl, and C1-C2 haloalkyl.

[0056] In certain embodiments, in formula (I.1) or (II), R 1 and R 6 R is independently selected from hydrogen, CF3, and A1, where R A , R B , R C , R D , and R E However, it is selected independently from hydrogen and CF3; R 2 and R 5 R is independently selected from hydrogen, CF3, and A1, where R A , R B , R C , R D , and R E It is selected independently from hydrogen and CF3; R 1 A and A, together with the carbon atoms to which they are bonded, form a phenyl ring, where phenyl is unsubstituted or has one or two identical or different free groups R 9 Replaced by; R 6 B and B, together with the carbon atoms to which they are bonded, form a phenyl ring, where phenyl is unsubstituted or has one or two identical or different free groups R 9 Replaced by; R 9 This is selected from CN, F, Cl, and CF3.

[0057] In another specific embodiment, R in formula (I.1) or (II) 2 and R 5 It is selected independently from hydrogen and CF3, and also R 1 and R 6 It is selected independently from CF3 and A1, where R A , R B , R C , R D , and R E However, it is either hydrogen or CF3, or R1 A and A, together with the carbon atoms to which they are bonded, form a phenyl ring, where phenyl is unsubstituted or has one or two identical or different free groups R 9 Replaced by; or, R 6 B and B, together with the carbon atoms to which they are bonded, form a phenyl ring, where phenyl is unsubstituted or has one or two identical or different free groups R 9 Replaced by; R 9 This is selected from CN, F, Cl, and CF3. Preferably, in equation (II), R 3 and R 4 However, these are independently selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, and C1-C6 haloalkoxy, or R 3 and R 4 However, along with the carbon atoms to which they are bonded, C6-C 14 An aryl group is formed, where the aryl is unsubstituted or consists of 1, 2, 3, or 4 identical or different free groups R 9 Replaced by; R 9 However, CN, halogen, C1-C6 alkyl, C1-C6 haloalkyl, or C6-C 14 Selected from aryls, where the aryl is either unsubstituted or substituted with 1, 2, 3, 4, or 5 identical or different substituents selected from C1-C4 alkyl or C1-C4 haloalkyl. It is a ligand of equation (II). Particularly preferable is that in equation (II), R 3 and R 4 However, independently of each other, they are selected from hydrogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, and phenyl, where phenyl is unsubstituted or has 1, 2, 3, or 4 identical or different free radicals R 9 Replaced by, or R 3 and R 4However, together with the carbon atoms to which they are bonded, they form a phenyl ring, where phenyl is either unsubstituted or has 1, 2, 3, or 4 identical or different free radicals R 9 Replaced by; R 9 However, selected from CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl, or phenyl, where phenyl is either unsubstituted or substituted with 1, 2, 3, or 4 identical or different substituents selected from C1-C4 alkyl or C1-C4 haloalkyl. It is a ligand of equation (II). Particularly preferable is that in equation (II), R 3 and R 4 However, it is independently selected from hydrogen, CN, C1-C2 alkyl, and CF3; R 3 and R 4 However, together with the carbon atoms to which they are bonded, they form a phenyl group, and here, phenyl is unsubstituted. It is a ligand of equation (II). Preferably, in formula (II), A and B are independent free radicals CR 7 And also, R 7 However, it is selected from hydrogen, CN, nitro, halogen, and group B consisting of B1, B2, B3, B4, B5, B6, B7, B8, B9, B10, B11, B12, B13, B14, and B15. In JPEG0007870555000015.jpg160128, # indicates bonding to the base of formula (II), and R F , R G , R H , R I , and R J However, it can be independently selected from hydrogen, CN, halogen, C1-C4 alkyl, and C1-C4 haloalkyl. It is a ligand of equation (I.1) or (II). Regardless of their appearance, free group R F , R G , R H , R I , and R JThe free radical is preferably selected from hydrogen, CN, fluorine, chlorine, C1-C4 alkyl, C1-C4 fluoroalkyl, and C1-C4 chloroalkyl. In a preferred embodiment, the free radical R F , R G , R H , R I , and R J These are hydrogen, CN, fluorine, or chlorine, all independent of each other. Preferably, in formula (II), A and B are independent free radicals CR 7 And R 7 However, R is selected from hydrogen, CN, nitro, halogen, C1-C2 alkyl, C1-C2 haloalkyl, and B1, where R F , R G , R H , R I , and R J However, each ligand is independently selected from hydrogen, CN, fluorine, and chlorine, and is of formula (I.1) or (II). Particularly preferred is that in formula (II), A and B are independent free groups CR 7 And R 7 However, it is selected from hydrogen, CN, nitro, halogen, C1-C2 alkyl, and C1-C2 haloalkyl, specifically, R 7 However, the ligand is selected from hydrogen, CN, nitro, fluorine, and chlorine, particularly hydrogen, fluorine, and CN, and is of formula (I.1) or (II).

[0058] In Embodiment A, the ligand of formula (II) is selected from formula (IA). JPEG0007870555000016.jpg3581X is O, R 1 The C3-C7 cycloalkyl group is selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, and C3-C7 cycloalkyl, where C3-C7 cycloalkyl is unsubstituted or CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, and NR. 4a R 4b, and substituted with 1, 2, 3, 4, 5, or 6 identical or different substituents selected from group A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, and A19 as defined above, R 2 The C3-C7 cycloalkyl group is selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, and C3-C7 cycloalkyl, where C3-C7 cycloalkyl is unsubstituted or CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, and NR. 4a R 4b , and substituted with 1, 2, 3, 4, 5, or 6 identical or different substituents selected from group A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, and A19 as defined above, R 5 The C3-C7 cycloalkyl group is selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, and C3-C7 cycloalkyl, where C3-C7 cycloalkyl is unsubstituted or CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, and NR. 4a R 4b , and substituted with 1, 2, 3, 4, 5, or 6 identical or different substituents selected from group A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, and A19 as defined above, R 6The C3-C7 cycloalkyl group is selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, and C3-C7 cycloalkyl, where C3-C7 cycloalkyl is unsubstituted or CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, and NR. 4a R 4b , and substituted with 1, 2, 3, 4, 5, or 6 identical or different substituents selected from group A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, and A19 as defined above, R 7 However, it is selected from hydrogen, CN, nitro, halogen, C1-C2 alkyl, and C1-C2 haloalkyl.

[0059] In Embodiment B, the ligand of formula (II) is selected from formula (IB). JPEG0007870555000017.jpg3773 Here, X represents O; R 1 And A, along with the carbon atoms to which they are bonded, C6~C 14 An aryl group or a hetalil group having 3 to 6 carbon atoms is formed, where the hetalil is N and NR 8 The ring members selected from have 1, 2, or 3 heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, or 4 identical or different free groups R 9 Replaced by; R 2 The C3-C7 cycloalkyl group is selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, and C3-C7 cycloalkyl, where C3-C7 cycloalkyl is unsubstituted or CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, and NR. 4a R4b , and substituted with 1, 2, 3, 4, 5, or 6 identical or different substituents selected from group A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, and A19 as defined above, R 5 The C3-C7 cycloalkyl group is selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, and C3-C7 cycloalkyl, where C3-C7 cycloalkyl is unsubstituted or CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, and NR. 4a R 4b , and substituted with 1, 2, 3, 4, 5, or 6 identical or different substituents selected from group A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, and A19 as defined above, R 6 And B, along with the carbon atoms to which they are bonded, C6~C 14 An aryl group or a hetalil group having 3 to 6 carbon atoms is formed, where the hetalil is N and NR 8 The ring members selected from have 1, 2, or 3 heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, or 4 identical or different free groups R 9 It will be replaced by this.

[0060] In Embodiment C, the ligand of formula (II) is selected from formula (IC). JPEG0007870555000018.jpg3670 Here, X represents O; R 1The C3-C7 cycloalkyl group is selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, and C3-C7 cycloalkyl, where C3-C7 cycloalkyl is unsubstituted or CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, and NR. 4a R 4b , and substituted with 1, 2, 3, 4, 5, or 6 identical or different substituents selected from group A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, and A19 as defined above, R 2 And A, along with the carbon atoms to which they are bonded, C6~C 14 An aryl group or a hetalil group having 3 to 6 carbon atoms is formed, where the hetalil is N and NR 8 The ring members selected from have 1, 2, or 3 heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, or 4 identical or different free groups R 9 Replaced by; R 5 And B, along with the carbon atoms to which they are bonded, C6~C 14 An aryl group or a hetalil group having 3 to 6 carbon atoms is formed, where the hetalil is N and NR 8 The ring members selected from have 1, 2, or 3 heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, or 4 identical or different free groups R 9 Replaced by; R 6The C3-C7 cycloalkyl group is selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, and C3-C7 cycloalkyl, where C3-C7 cycloalkyl is unsubstituted or CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, and NR. 4a R 4b and are substituted with one, two, three, four, five, or six identical or different substituents selected from group A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, and A19 as defined above.

[0061] In embodiment D, the ligand of formula (II) is selected from formula (ID). JPEG0007870555000019.jpg4077R 1 The C3-C7 cycloalkyl group is selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, and C3-C7 cycloalkyl, where C3-C7 cycloalkyl is unsubstituted or CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, and NR. 4a R 4b , and substituted with one, two, three, four, five, or six identical or different substituents selected from group A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, and A19 as defined above; R 2 The C3-C7 cycloalkyl group is selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, and C3-C7 cycloalkyl, where C3-C7 cycloalkyl is unsubstituted or CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, and NR. 4a R 4b, and substituted with one, two, three, four, five, or six identical or different substituents selected from group A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, and A19 as defined above; R 3 and R 4 However, along with the carbon atoms to which they are bonded, C6~C 14 An aryl group or a hetalil group having 3 to 6 carbon atoms is formed, where the hetalil is N and NR 8 The ring members selected from have 1, 2, or 3 heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, or 4 identical or different free groups R 9 Replaced by; R 5 The C3-C7 cycloalkyl group is selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, and C3-C7 cycloalkyl, where C3-C7 cycloalkyl is unsubstituted or CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, and NR. 4a R 4b , and substituted with one, two, three, four, five, or six identical or different substituents selected from group A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, and A19 as defined above; R 6 The C3-C7 cycloalkyl group is selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, and C3-C7 cycloalkyl, where C3-C7 cycloalkyl is unsubstituted or CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, and NR. 4a R 4b, and substituted with one, two, three, four, five, or six identical or different substituents selected from group A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, and A19 as defined above; R 7 However, it is selected from hydrogen, CN, nitro, halogen, C1-C2 alkyl, and C1-C2 haloalkyl.

[0062] In embodiment E, the ligand of formula (II) is selected from formula (IE). JPEG0007870555000020.jpg4072 Here, R 1 And A, along with the carbon atoms to which they are bonded, C6~C 14 An aryl group or a hetalil group having 3 to 6 carbon atoms is formed, where the hetalil is N and NR 8 The ring members selected from have 1, 2, or 3 heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, or 4 identical or different free groups R 9 Replaced by; R 2 The C3-C7 cycloalkyl group is selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, and C3-C7 cycloalkyl, where C3-C7 cycloalkyl is unsubstituted or CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, and NR. 4a R 4b , and substituted with one, two, three, four, five, or six identical or different substituents selected from group A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, and A19 as defined above; R 3 and R 4 However, along with the carbon atoms to which they are bonded, C6~C 14An aryl group or a hetalil group having 3 to 6 carbon atoms is formed, where the hetalil is N and NR 8 The ring members selected from have 1, 2, or 3 heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, or 4 identical or different free groups R 9 Replaced by; R 5 The C3-C7 cycloalkyl group is selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, and C3-C7 cycloalkyl, where C3-C7 cycloalkyl is unsubstituted or CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, and NR. 4a R 4b , and substituted with one, two, three, four, five, or six identical or different substituents selected from group A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, and A19 as defined above; R 6 And B, along with the carbon atoms to which they are bonded, C6~C 14 An aryl group or a hetalil group having 3 to 6 carbon atoms is formed, where the hetalil is N and NR 8 The ring members selected from have 1, 2, or 3 heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, or 4 identical or different free groups R 9 It will be replaced by this.

[0063] In embodiment F, the ligand of formula (II) is selected from formula (IF). JPEG0007870555000021.jpg4074 Here, R 1However, the C3-C7 cycloalkyl is selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, and C3-C7 cycloalkyl, where C3-C7 cycloalkyl is unsubstituted or CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b , and substituted with one, two, three, four, five, or six identical or different substituents selected from group A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, and A19 as defined above; R 2 And A, along with the carbon atoms to which they are bonded, C6~C 14 An aryl group or a hetalil group having 3 to 6 carbon atoms is formed, where the hetalil is N and NR 8 The ring members selected from have 1, 2, or 3 heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, or 4 identical or different free groups R 9 Replaced by; R 3 and R 4 However, along with the carbon atoms to which they are bonded, C6~C 14 An aryl group or a hetalil group having 3 to 6 carbon atoms is formed, where the hetalil is N and NR 8 The ring members selected from have 1, 2, or 3 heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, or 4 identical or different free groups R 9 Replaced by; R 5 And B, along with the carbon atoms to which they are bonded, C6~C 14 An aryl group or a hetalil group having 3 to 6 carbon atoms is formed, where the hetalil is N and NR 8The ring members selected from have 1, 2, or 3 heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, or 4 identical or different free groups R 9 Replaced by; R 6 The C3-C7 cycloalkyl group is selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, and C3-C7 cycloalkyl, where C3-C7 cycloalkyl is unsubstituted or CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, and NR. 4a R 4b and are substituted with one, two, three, four, five, or six identical or different substituents selected from group A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, and A19 as defined above.

[0064] In a preferred embodiment, the compound of formula (I) is wherein the ligand of formula (II) is: JPEG0007870555000022.jpg5074 Here, CR 3 Base and CR 4 Between JPEG0007870555000023.jpg617 refers to a single bond or a double bond; X is O; A and B are independent of each other and CR 7 And here, R 7 However, it is selected from H and CN; R 1 and R 6 However, independently selected from hydrogen, CH3, CF3, C2F5, and phenyl; or, R 1 And A, together with the carbon atoms to which they are bonded, form [4-(trifluoromethyl)phenyl], or, R 6And B, together with the carbon atoms to which they are bonded, form [4-(trifluoromethyl)phenyl]; R 3 and R 4 However, it represents hydrogen, or, R 3 and R 4 However, together with the carbon atoms to which they are bonded, they form phenyl or (3,4-difluorophenyl); R 2 and R 5 However, it is independently selected from hydrogen, CH3, CF3, C2F5, phenyl, and [3-chloro-4-(trifluoromethyl)phenyl]. In particular, the above compound is Regardless of their appearance, free radicals R 4a and R 4b The element is preferably selected from hydrogen and C1-C4 alkyl groups. Regardless of its appearance, free group R 8 The C1-C4 alkyl and C1-C4 haloalkyl groups are preferably selected from C1-C4 alkyl and C1-C4 haloalkyl groups. Regardless of its appearance, free group R 9 The is preferably selected from CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl, and phenyl, where phenyl is unsubstituted or substituted with 1, 2, 3, 4, or 5 identical or different free radicals selected from C1-C4 alkyl and C1-C4 haloalkyl. In particular, R 9 R is selected from CN, halogen, C1-C2 alkyl, and C1-C2 haloalkyl. In particular, 9 This is selected from CN, F, Cl, and CF3. Regardless of its appearance, free group R 12 The free radicals are preferably selected from halogens, CN, C1-C4 alkyl, C1-C4 haloalkyl, and phenyl, where phenyl is unsubstituted or has 1, 2, 3, or 4 identical or different free radicals R 9 It will be replaced by this.

[0065] component In the context of the present invention, an electronic component is understood to be an individual or integrated electronic component that utilizes the properties of a compound of general formula (I) or a semiconductor matrix material containing a compound of general formula (I). In a particular embodiment, the electronic component has a layered structure comprising two, three, four, five, six, seven, or more layers, wherein at least one layer contains at least one compound of general formula (I). Each layer may contain an inorganic material, or the component may include layers composed entirely of inorganic materials.

[0066] Preferably, the electronic component is selected from organic field-effect transistors (OFETs), organic electroluminescent devices, organic solar cells (OSCs), electrophotography devices, organic optical detectors, organic photodetectors, organic photoreceptors, light-emitting electrochemical cells (LECs), and organic laser diodes. The organic field-effect transistor (OFET) is preferably an organic thin-film transistor (OTFT). The organic electroluminescent device is preferably an organic light-emitting diode (OLED). The organic solar cell is preferably an exciton solar cell, a dye-sensitized solar cell (DSSC), or a perovskite solar cell. The electrophotography device is preferably a photoconductive material in an organic photoconductor (OPC).

[0067] Preferably, the electronic component according to the present invention is in the form of an organic light-emitting diode, an organic solar cell, a solar cell, an organic sensor, an organic diode, or an organic transistor, preferably a field-effect transistor, a thin-film transistor, or a perovskite solar cell.

[0068] The electronic component may preferably be an organic electroluminescent device in the form of an organic light-emitting diode (OLED). The organic electroluminescent device includes a positive electrode, a negative electrode, and at least one light-emitting layer. In addition to these layers, it may also include other layers, such as one or more vacancy injection layers, vacancy transport layers, vacancy blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, and / or charge generation layers. For example, an intermediate layer having an exciton blocking function may be inserted between two light-emitting layers. These layers do not necessarily all need to be present.

[0069] A preferred embodiment is an electronic component, particularly in the form of an OLED, where the layer containing the compound of formula (I) is a vacancy transport layer or a vacancy injection layer. Generally, a vacancy injection layer is a layer that facilitates electron injection from the negative electrode to an organic semiconductor matrix material. The vacancy injection layer may be located directly adjacent to the negative electrode. A vacancy transport layer transports vacancies from the negative electrode to the light-emitting layer and is located between the vacancy injection layer and the light-emitting layer.

[0070] A preferred embodiment is an electronic component in the form of an organic solar cell. Generally, an organic solar cell is layered and typically includes at least the following layers: a negative electrode, at least one photoactive layer, and a positive electrode. These layers are generally applied to a substrate commonly used for this purpose. The photoactive region of the solar cell may include two layers, each having a uniform composition, forming a planar donor-acceptor heterojunction. The photoactive region may also include a mixed layer, forming a donor-acceptor heterojunction in the form of a donor-acceptor bulk heterojunction. In addition to these layers, the organic solar cell may also include other layers selected, for example, from the following: — A layer having the characteristics of an electron transport layer (electron transport layer, ETL), — Layers containing vacancy-conducting materials (vacancy transport layers, HTLs) (these must not absorb radiation), — Exciton and vacancy barrier layers (EBL, etc.) (these must not be absorbed), and - Multiple layers.

[0071] Another preferred embodiment is an electronic component in the form of an organic solar cell, where a layer containing the compound of formula (I) has electron-conducting properties (electron transport layer, ETL).

[0072] A particular embodiment is an electronic component in the form of an organic solar cell, where a layer comprising at least one compound of formula (I) is part of a pn junction connecting a light-absorbing unit to an additional light-absorbing unit in a tandem or multi-stack configuration, and / or part of a pn junction connecting a positive or negative electrode to a light-absorbing unit.

[0073] Another preferred embodiment is an electronic component comprising an electron transport layer containing at least one compound of formula (I).

[0074] Semiconductor matrix materials The compounds of formula (I) according to the present invention and used in accordance with the present invention, as well as their charge transfer complexes and their reduced products, can be used as doping agents in organic semiconductor matrix materials, in particular as p-dopants in vacancy transport layers. The doped semiconductor matrix material preferably comprises at least one electron donor and at least one compound of formula (I) as defined above.

[0075] A suitable diaminoterphenyl is described in German Patent No. 102012007795. Diaminotrimethylphenylindan is described in International Publication No. 2018 / 206769.

[0076] In particular, the electron donors are 4,4',4"-tris(N-(2-naphthyl)-N-phenyl-amino)triphenylamine (2-TNATA), 4,4',4"-tris(N-3-methylphenyl-N-phenyl)-amino)triphenylamine (m-MTDATA), N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine (MeO-TPD), (2,2',7,7'-tetrakis-(N,N-diphenylamino)-9,9'-spirobifluorene (Spiro-TTB), N,N'-bis(naphthalene-1-yl)-N,N'-bis(phenyl)-benzidine, N,N'-bis(naphthalene-1-yl)-N,N'-bis(phenyl)-9,9-spirobifluorene, 9,9-bis[4-(N,N-bis-biphenyl-4-yl- [amino)phenyl]-9H-fluorene, 2,2'-bis[N,N-bis(biphenyl-4-yl)amino]-9,9-spiro-bifluorene, N,N'-((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine)(BPAPF), N,N'-bis(phenane Tren-9-yl)-N,N'-bis(phenyl)-benzidine, 1,3,5-tris{4-[bis(9,9-dimethyl-fluoren-2-yl)amino]phenyl}benzene, tri(terphenyl-4-yl)amine, N-(4-(6-((9,9-dimethyl-9H-fluoren-2-yl)(6-methoxy-[1,1'-biphenyl]-3-yl)amino)-1,3,3 -trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(6-methoxy-[1,1'-biphenyl]-3-yl)-9,9-dimethyl-9H-fluoren-2-amine, N-([1,1'-biphenyl]-4-yl)-N-(4-(6-([1,1'-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine, N,N-di([1,1'-biphenyl]-4-yl)-3-(4-(di([1,1'-biphenyl]-4-yl)amino)phenyl)-1,1,3-trimethyl-2,3-dihydro-1H-inden-5-amine, N-(4-(6-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine, N-(4-(6-(9,9'-spirobio[fluoren]-2-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl Phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio[fluorene]-2-amine, N-(4-(6-(dibenzo[b,d]furan-2-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3)-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-2-amine, 9-(4-(6-(9H-carbazole-9-yl)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl Den-1-yl)phenyl)-9H-carbazole, N-([1,1'-biphenyl]-4-yl)-3-(4-([1,1'-biphenyl]-4-yl(4-methoxyphenyl)amino)phenyl)-N-(4-methoxyphenyl)-1,1,3-trimethyl-2,3-dihydro-1H-inden-5-amine, 3-(4-(bis(6-methoxy-[1,1'-biphenyl]-3-yl)amino)phenyl)-N,N-bis(6-methoxy-[1,1'-biphenyl]-3-yl)-1,1,3-trimethyl-2,3-dihydro-1H-inden- 5-amine, N1-([1,1'-biphenyl]-4-yl)-N1-(4-(6-([1,1'-biphenyl]-4-yl(4-(diphenylamino)phenyl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, N,N-di([1,1'-biphenyl]-4-yl)-4'-(6-(4-(di([1,1'-biphenyl]-4-yl)amino)phenyl)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)-[1,1'-biphenyl]-4-amine, N-(4-(5-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine, N-(4-(6-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren) Olen-2-yl)-9,9-dimethyl-9H-fluoren-2-amine, N,N'-bis(9,9-dimethyl-fluoren-2-yl)-N,N'-diphenyl-benzidine (BF-DPB), N,N'-((9H-fluoren-9,9-diyl)bis(4,1-phenylene))bis(N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine)(BPAPF), N4,N4,N4',N4'-tetrakis(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-4,4'-diamine (TDMFB), N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio[fluoren]-2-amine, (2,7-bis[N,N-bis(4-methoxyphenyl)amino]-9,9-spirobio[9H-fluoren](spiro-MeO-TPD), N-(4-(5-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9- A mixture of dimethyl-9H-fluoren-2-amine and N-(4-(6-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluoren-2-amine, and mixtures thereof are selected.

[0077] Naturally, other suitable organic semiconductor matrix materials, particularly porous conductive materials with semiconductor properties, can also be used.

[0078] doping Doping can be carried out, in particular, when the molar ratio of the matrix molecular pair of formula (I) is 10000:1 to 1:1, preferably 1000:1 to 2:1, and especially 5:1 to 100:1.

[0079] Preparation of doped semiconductor matrix materials The doping of a specific matrix material (hereinafter also referred to as vacancy-conducting matrix HT) with a compound of general formula (I) according to the present invention can be produced by one or a combination of the following processes. a) Mix and evaporate the HT source and the source of at least one compound of general formula (I) in a vacuum. b) HT and at least one compound of general formula (I) are sequentially deposited, followed by internal diffusion of the doping agent by heat treatment. c) The HT layer is doped with a solution of at least one compound of general formula (I), and then the solvent is evaporated by heat treatment. d) Doping the surface of the HT layer by coating one or both sides with a layer of at least one compound of general formula (I). e) Prepare a solution of a host and at least one compound of general formula (I), and form a film from the solution by, for example, coating, casting, printing, or other film preparation techniques known to those skilled in the art.

[0080] Another object of the present invention is the use of compound (I) or a mixture thereof as defined above. — Organic semiconductors, — Redox doping agents in organic semiconductor matrix materials, particularly p-dopant in vacancy transport layers and - Electron transport materials, — Charge injector in charge injection layer, — Cathode materials in organic batteries, — Electrochromic materials

[0081] A further object of the present invention is the use of Ce(III) composite anions obtained by reduction of compound (I) as defined above, or charge transfer composites of compound (I) as defined above and an electron donor, as organic semiconductors or electrochromic materials.

[0082] A further object of the present invention is a compound of general formula (I), Ce 4+ [L1L2] 4- (I) These are charge transfer complexes, their reduced products, and mixtures thereof. In the formula, L1 and L2 are ligands of formula (I.1), respectively. A tetradentate ligand independently selected from JPEG0007870555000025.jpg5886, in the formula, X represents either O or S independently of each other; Z is a bridging group having two or three carbon atoms between nitrogen atoms, where each carbon atom is either unsubstituted or one, two, three, four, five, or six identical or different free groups R 12 Substituted, where two adjacent carbon atoms may be linked to each other by a double bond, or two or three of the carbon atoms may be mononuclear, dinuclear, or trinuclear C6-C 14 It is part of an aromatic or heteroaromatic ring system, where the heteroaromatic ring system has 4 to 13 carbon atoms, and also contains N, NR 8 The aromatic or heteroaromatic ring system has one, two, or three identical or different heteroatoms or heteroatom-containing groups as ring members selected from O, S, SO, and SO2, wherein the aromatic or heteroaromatic ring system is either unsubstituted or has one, two, three, four, or five identical or different free groups R 9 Replaced by; A and B are independent of each other and are N or CR 7 It represents; R1 and R 6 However, the free radicals are independently selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, and C3-C7 cycloalkyl, where the C3-C7 cycloalkyl is unsubstituted or has 1, 2, 3, 4, 5, or 6 identical or different free radicals R 11 , C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b , C6-C having 4 to 13 carbon atoms 14 Replaced with aryl and hetalir, where hetalir is N, NR 8 The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 9 Replaced by; or, R 1 And A, along with the carbon atoms to which they are bonded, C6-C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 The ring members selected from O, S, SO, and SO2 have one, two, or three identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have one, two, three, or four identical or different free groups R 9 Replaced by, or R 6 And B, along with the carbon atoms to which they are bonded, C6-C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 The ring members selected from O, S, SO, and SO2 have one, two, or three identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have one, two, three, or four identical or different free groups R 9 Replaced by; R2 and R 5 However, the following are independently selected from hydrogen, CN, C1-C6 alkyl, C1-C6-haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, and C3-C7 cycloalkyl, where the C3-C7 cycloalkyl is unsubstituted or has 1, 2, 3, 4, 5, or 6 identical or different free radicals R 11 , C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b , C6-C having 4 to 13 carbon atoms 14 Replaced with aryl and hetalir, where hetalir is N, NR 8 The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 9 Replaced by; R 2 And A, along with the carbon atoms to which they are bonded, C6-C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 The ring members selected from O, S, SO, and SO2 have one, two, or three identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have one, two, three, or four identical or different free groups R 9 Replaced by; R 5 And B, along with the carbon atoms to which they are bonded, C6-C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 The ring members selected from O, S, SO, and SO2 have one, two, or three identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have one, two, three, or four identical or different free groups R 9 Replaced by; R 4aR 4b However, independently of each other, hydrogen, C1-C6 alkyl, and C6-C 14 Selected from aryl groups, where the aryl group is unsubstituted or consists of 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 7 However, hydrogen, CN, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b , C6-C having 4 to 13 carbon atoms 14 Selected from aryl and hetalir, where hetalir is N, NR 8 The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 10 Replaced by; R 8 However, hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C6-C 14 Selected from aryls, where the aryl is unsubstituted or consists of 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 9 However, CN, halogen, C1-C6 alkyl, C1-C6 haloalkyl, and C6-C 14 Selected from aryl groups, where the aryl group is either unsubstituted or substituted with 1, 2, 3, 4, or 5 identical or different free radicals selected from C1-C4 alkyl and C1-C4 haloalkyl groups; R 10 However, these are selected from CN, halogen, C1-C4 alkyl, and C1-C4 haloalkyl; R 11 However, these are selected from CN, halogen, C1-C4 alkyl, and C1-C4 haloalkyl; R 12However, the C3-C7 cycloalkyl group is independently selected from halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, and C3-C7 cycloalkyl groups, where the C3-C7 cycloalkyl group is either unsubstituted or has 1, 2, 3, 4, 5, or 6 identical or different free radicals R 11 , C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b , C6-C having 4 to 13 carbon atoms 14 Replaced with aryl and hetalir, where hetalir is N, NR 8 The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 9 Replaced by; However, the following compounds are excluded: JPEG0007870555000026.jpg201128.

[0083] A further object of the present invention is a compound of general formula (I), Ce 4+ [L1L2] 4- (I) These are charge transfer complexes, their reduced products, and mixtures thereof. In the formula, L1 and L2 are ligands of formula (II), respectively. A tetradentate ligand independently selected from JPEG0007870555000027.jpg5074, in the formula, CR 3 Base and CR 4 Between JPEG0007870555000028.jpg617 represents a single bond or a double bond; X represents either O or S independently of each other; A and B are independent of each other and are N or CR 7 It represents; R 1 and R 6However, hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b , C6-C having 4 to 13 carbon atoms 14 Selected independently from aryl and hetalir, where hetalir is N, NR 8 The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 9 Replaced by; or, R 1 And A, along with the carbon atoms to which they are bonded, C6-C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 The ring members selected from O, S, SO, and SO2 have one, two, or three identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have one, two, three, or four identical or different free groups R 9 Replaced by, or R 6 And B, along with the carbon atoms to which they are bonded, C6-C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 The ring members selected from O, S, SO, and SO2 have one, two, or three identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have one, two, three, or four identical or different free groups R 9 Replaced by; R 3 and R 4 However, hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR4a R 4b , C6-C having 4 to 13 carbon atoms 14 Selected independently from aryl and hetalir, where hetalir is N, NR 8 The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 9 Replaced by, or R 3 and R 4 However, along with the carbon atoms to which they are bonded, C6-C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 The ring members selected from O, S, SO, and SO2 have one, two, or three identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have one, two, three, or four identical or different free groups R 9 Replaced by; R 2 and R 5 However, hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b , C6-C having 4 to 13 carbon atoms 14 Selected independently from aryl and hetalir, where hetalir is N, NR 8 The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 9 Replaced by; R 4a R 4b However, independently of each other, hydrogen, C1-C6 alkyl, and C6-C 14Selected from aryl groups, where the aryl group is unsubstituted or consists of 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 7 However, hydrogen, CN, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR 4a R 4b , C6-C having 4 to 13 carbon atoms 14 Selected from aryl and hetalir, where hetalir is N, NR 8 The ring member selected from O, S, SO, and SO2 has one, two, or three identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or have one, two, three, four, or five identical or different free groups R 10 Replaced by; R 8 However, hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C6-C 14 Selected from aryl groups; where the aryl group is unsubstituted or consists of 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 9 However, CN, halogen, C1-C6 alkyl, C1-C6 haloalkyl, and C6-C 14 Selected from aryl groups; where the aryl group is unsubstituted or substituted with 1, 2, 3, 4, or 5 identical or different free radicals selected from C1-C4 alkyl and C1-C4 haloalkyl groups; R 10 However, it is selected from CN, halogen, C1-C4 alkyl, and C1-C4 haloalkyl. However, the compounds of formula (I) below and their reaction products are excluded: L1 = L2 = N,N'-bis(4,4,4,-trifluorobuto-1-en-3-one)-ethylenediamine, L1 = L2 = N,N'-bis(4,4,5,5,5-pentafluoropento-1-en-3-one)-ethylenediamine, L1 = L2 = N,N'-bis(4,4,5,5,6,6,6-heptafluorohex-1-en-3-one)-ethylenediamine, Furthermore, the following compounds and their reaction products are excluded: JPEG0007870555000029.jpg193138.

[0084] The following examples illustrate the present invention, but are not intended to limit it. [Examples]

[0085] Abbreviation: APCI-MS Atmospheric Pressure Chemical Ionization-Mass Spectrometer DCM Dichloromethane DEM Ethylene Glycol Dimethyl Ether HTM vacancy transport material MeCN acetonitrile iPrOH Isopropanol EDTA (Ethylenediaminetetraacetic acid) Cerium isopropoxide was prepared according to “Gradeff, PS et al., Journal of the less common metals, Vol. 126, 1986, 335-338.” Sample preparation for conductivity measurement: Doped thin film samples were prepared using glass substrates equipped with patterned 50 nm thick Au electrodes with a channel length of 100 μm. The layers were deposited by either thermal evaporation or deposition from the liquid phase, e.g., rotary coating. Thermal evaporation was performed at room temperature and high vacuum (base pressure: 5x10⁻¹⁰). -7 The procedure was performed at a pressure of less than mbar. The vacancy transport material (HTM) and dopant were co-deposited according to a dopant concentration of 20 wt%, and the evaporation rate was controlled by two independent quartz microbalances. The liquid-treated film was spatula coated with a chlorobenzene solution of HTM and dotand at 3000 rpm. The concentrations of HTM and dotand were nominally 10 wt%. The layer was then baked at 80°C for 5 minutes. The film thickness was checked by profilometry and ranged from 50 to 110 nm. Characterization: The lateral conductivity of the coating was measured from the gradient of the current-voltage characteristic between -10 and 10 V. For coatings treated with liquid processing in air, this measurement was performed immediately after sample preparation for in-situ thermal evaporation coatings in high vacuum.

[0086] Synthesis of 1: JPEG0007870555000030.jpg4968 This synthesis was carried out according to the reference J. Schlafer, D. Graf, G. Fornalczyk, A. Mettenborger, S. Mathur, Inorg. Chem. 2016, 55, 5422-5429. In cyclic voltammetry of dichloromethane (DCM, 200 mV / s, 0.1M NBu4PF6), the following results were obtained: E 1 / 2 (vs. Fc / Fc + ) = -0.51V. Compound 1 was subjected to an external temperature of 140°C and a pressure of 10°C. -2 Sublimation occurs with no residue using mbar.

[0087] Composition of 2: The preparation of 4,4,4-trifluoro-3-oxobutanenitrile was carried out in accordance with International Publication No. 2005 / 49033. 4,4,4-trifluoro-3-oxobutanenitrile (1.9 g, 13.9 mmol) was dissolved in acetic anhydride (Ac2O, 5 ml) and (EtO)3CH (2.05 g, 13.9 mmol). The reaction mixture was refluxed for 1 hour. Subsequently, all volatile components were removed under vacuum. The brown residue was dissolved in dichloromethane (DCM, 20 ml), and 1,2-diaminoethane (0.2 ml) was added. The white precipitate was filtered off (0.079 g, 0.22 mmol, 1.6%). The mass spectrum of the ligand was obtained from [MH]. + It showed ;353. The ligand (76 mg, 0.21 mmol) was added to a 0.3 M Ce2(OiPr)8(HOiPr)2 (0.17 ml, 0.055 mmol) ethylene glycol dimethyl ether / ipropanol solution (DME / iOrOH, 1:1 v / v) under N2 conditions. After 30 minutes, the solvent was removed. A red solid of compound 2 was obtained (0.078 mg). The mass spectrum of compound 2 was [MH]. - It showed ;843. In cyclic voltammetry of acetonitrile (ACN, 200 mV / s, 0.1M NBu4PF6), the following results were obtained: E 1 / 2 (vs. Fc / Fc + ) = +0.40V.

[0088] Synthesis of 3: The ligand synthesis was carried out according to the following reference: Gurley, L.; Beloukhina, N.; Boudreau, K.; Klegeris, A.; McNeil, WS Journal of Inorganic Biochemistry 2011, 105, 6, 858-866. In the presence of N2, 1 (120 mg, 0.26 mmol) of compound 3 was added to a 0.4 M Ce2(OiPr)8(HOiPr)2 (0.33 ml, 0.131 mmol) ethylene glycol dimethyl ether / ipropanol solution (DME / iPrOH) (1:1 v / v). After 30 minutes, the solvent was removed and the solid was washed with diethyl ether (Et2O). 56 mg of a red solid of compound 3 was obtained. The mass spectrum of compound 3 was [MH]. - It showed ;1047. In cyclic voltammetry of 3 in acetonitrile (ACN, 200 mV / s, 0.1M NBu4PF6), the following results were obtained: E 1 / 2 (vs. Fc / Fc + ) = -0.36V.

[0089] Synthesis of 4: JPEG0007870555000033.jpg51853,5-Bistrifluoromethylacetophenone (8 g, 31.3 mmol) was dissolved in ethanol (40 ml), and acetic acid (0.1 ml) was added. Then, 1,2-diaminoethane (0.94 g, 15.6 mmol) was added, and the solution was heated in a pressure tube at 90°C for 12 hours. Upon cooling to -20°C, colorless crystals were formed and filtered off. After drying in vacuum, 2.0 g (0.37 mmol, 24%) of colorless solid, N1,N2-bis(1-(3,5-bis(trifluoromethyl)phenyl)vinyl)ethane-1,2-diamine was obtained. APCI-MS (positive): 537.3 [M+H] + N1,N2-bis(1-(3,5-bis(trifluoromethyl)phenyl)vinyl)ethane-1,2-diamine (9.72 g, 18.1 mmol) was suspended in DCM (50 ml), and anhydrous trifluoroacetic acid (8.37 g, 39.8 mmol) was added. After stirring at room temperature for 12 hours, the reaction solution was cooled to -20°C, and the white solid was filtered off. The solid was recrystallized from acetonitrile (50 ml) and filtered off. A white solid of 4,4'-(ethane-1,2-diylbis(azandiyl))bis(4-(3,5-bis(trifluoromethyl)phenyl)-1,1,1-trifluorobuto-3-en-2-one) was obtained in 4.16 g (5.71 mmol, 31%). APCI-MS (positive): 729.4 [M+H] + 4,4'-(ethane-1,2-diylbis(azandiyl))bis(4-(3,5-bis(trifluoromethyl)phenyl)-1,1,1-trifluorobuto-3-en-2-one) (2 g, 2.74 mmol) was added to a solution of cerium(IV) isopropoxide (0.32 M DME / iPrOH solution, 4.3 ml, 1.37 mmol). After stirring for 12 hours, the suspension was filtered and washed with DME. A red solid of 1.9 g (1.19 mmol, 87%) of cerium bis((2Z,2'Z,4Z,4'Z)-4,4'-(ethane-1,2-diylbis(azanylylide))bis(4-(3,5-bis(trifluoromethyl)phenyl)-1,1,1-trifluorobuto-2-en-2-oleate)) (4) was obtained. APCI-MS (positive): 1593 [M+H] + Metal composite (4) (538 mg) is used at 200°C and 4x10 -6 Sublimation was performed at mbar. The yield was 335 mg (62%). The metal complex (4) decomposes at 260°C. The following results were obtained from cyclic voltammetry of 4 in acetonitrile (ACN, 200 mV / s, 0.1M NBu4PF6): E 1 / 2 (vs. Fc / Fc + ) = -0, 12V. When spiro-MeO-TAD (CAS No.: 207739-72-8) is doped with 20 wt% dopant (4), after solvent treatment (rotary coating), a maximum of 1.5 x 10⁻¹⁰ -6 Conductivity increases up to S / cm were measured. The intrinsic conductivity of undoped spiro-MeO-TAD is 2 x 10⁻¹⁰. -8 It was measured to be S / cm.

[0090] Synthesis of 5: JPEG0007870555000034.jpg341041-(2-hydroxy-5-(trifluoromethyl)phenyl)ethane-1-one (1.19 g, 0.583 mmol) and 1,2-diaminoethane (0.18 g, 0.29 mmol) were dissolved in DCM and stirred for 12 hours. The solid was then filtered off. A white solid of 0.63 g (1.45 mmol, 50%) of 2,2'-(-(ethane-1,2-diylbis(azaneyllidene))bis(ethane-1-yl-1-ylidene))bis(4-(trifluoromethyl)phenol) was obtained. APCI-MS (positive): 433.3 [M+H] + 2,2'-(-(ethane-1,2-diylbis(azaneyllidene))bis(ethane-1-yl-1-ylidene))bis(4-(trifluoromethyl)phenol) (0.59 g, 1.36 mmol) was added to a solution of cerium(IV) isopropoxide (0.32 M DME / iPrOH solution, 0.68 mmol, 2.12 ml). The solvent was removed, and the residue was washed with hexane. The residue was dissolved in CHCl3, filtered, precipitated with hexane, and filtered off. An orange-red solid of cerium bis((2,2'-((1E,1'E)-(ethane-1,2-diylbis(azanylylidene))bis(ethane-1-yl-1-ylidene))bis(4-(trifluoromethyl)phenolate))(5) was obtained in 0.42 g (0.42 mmol, 62%). APCI-MS (positive): 1001[M+H] + Metal composite (5) (350 mg) is suitable for use at 180-200°C and 4x10 -6 Sublimation was performed using mbar. The yield was 12 mg (0.3%). In cyclic voltammetry of cetonitrile (ACN, 200 mV / s, 0.1M NBu4PF6), the following results were obtained: E 1 / 2 (vs. Fc / Fc + ) = +0,3V.

[0091] Synthesis of 6: JPEG0007870555000035.jpg3787 Ethylenediamine (830 mg, 13.6 mmol) was added to 50 ml of dichloromethane solution of 2-benzoyl-3-ethoxyacrylonitrile (5.54 g, 27.6 mmol) and stirred at room temperature. After 2 hours, a precipitate formed, which was filtered off and washed with dichloromethane. After drying in vacuum, 2.75 g (7.43 mmol, 55%) of (2Z,2'E)-2,2'-((ethane-1,2-diylbis(azandiyl))bis(metanylylidene))bis(3-oxo-3-phenylpropanenitrile) was obtained. 2.67 g (7.2 mmol) of (2Z,2'E)-2,2'-((ethane-1,2-diylbis(azandiyl))bis(metanylylidene))bis(3-oxo-3-phenylpropanenitrile) was added to a solution of cerium isopropoxide (11.25 ml, 3.6 mmol). The brown solid was filtered off and washed with DME (15 ml) and hexane (20 ml). The solid was then washed three times with a total of 200 ml of dichloromethane, and the washing solution was filtered. The washing solution was concentrated by half, and hexane (100 ml) was added. The resulting microcrystalline dark solid was filtered and dried in vacuum. 1.80 g (2.05 mmol, 57%) of (6) was obtained. (6) was decomposed at 170 °C. The following results were obtained from cyclic voltammetry of 6 in acetonitrile (ACN, 200 mV / s, 0.1M NBu4PF6): E 1 / 2 (vs. Fc / Fc + ) = -0, 1V.

[0092] Synthesis of 7: Phenylenediamine (1.62 g, 15 mmol) and (E)-4-ethoxy-1,1,1-trifluorobuto-3-en-2-one (5 g, 30 mmol) were added together and stirred in 100 ml of dichloromethane at room temperature for 2 days. The solution was concentrated by half, and then 100 ml of pentane was added. The microcrystalline solid, 4,4'-(1,2-phenylenebis(azanylylidene))bis(1,1,1-trifluorobuto-2-en-2-ol) (2.04 g, 5.80 mmol), was filtered and dried under vacuum. 4.12 g (11.7 mmol, 78%) was isolated. 4,4'-(1,2-phenylenebis(azanyllidene))bis(1,1,1-trifluorobuto-2-en-2-ol) (2.04 g, 5.80 mmol) was added to cerium(IV) isopropoxide solution (0.32 M DME / iPrOH solution, 9 ml, 2.89 mmol). The resulting red solid was filtered off and washed with DME. 1.08 g (1.39 mmol, 48%) of a dark red solid (7) was obtained. APCI-MS (positive): 841.1 [M+H] + Metal composite (7) (1.00 g) is suitable for use at 180-210°C and 3x10 -6 Sublimation was performed at mbar. The yield was 205 mg (20%). The metal complex (7) decomposes at 237°C. The following results were obtained from cyclic voltammetry of cetonitrile (ACN, 200 mV / s, 0.1M NBu4PF6): E 1 / 2 (vs. Fc / Fc + ) = -0.09V.

[0093] Synthesis of 8: JPEG0007870555000037.jpg53784,5-difluorobenzene-1,2-diamine (2.14 g, 15 mmol) and (E)-4-ethoxy-1,1,1-trifluorobuto-3-en-2-one (5 g, 30 mmol) were combined and stirred in 500 ml of dichloromethane at room temperature for 2 days. 100 ml of dichloromethane was removed under vacuum and 200 ml of pentane was added. The microcrystalline solid, (2Z,2'Z,4E,4'E)-4,4'-((4,5-difluoro-1,2-phenylene)bis(azanyllidene))bis(1,1,1-trifluorobuto-2-en-2-ol), was filtered and dried under vacuum. 3.60 g (9.27 mmol, 62%) was isolated. 4,4'-((4,5-difluoro-1,2-phenylene)bis(azanyllidene))bis(1,1,1-trifluorobuto-2-ene-2-ol) (2.50 g, 6.44 mmol) was added to a solution of cerium(IV) isopropoxide (0.32 M DME / iPrOH solution, 4.3 ml, 1.37 mmol). The suspension was filtered, and the red solid was washed with a small amount of DME and hexane. A deep red solid of 0.70 g (0.77 mmol, 12%) of cerium bis((2Z,2'Z,4E,4'E)-4,4'-((4,5-difluoro-1,2-phenylene)bis(azanyllidene))bis(1,1,1-trifluorobuto-2-ene-2-oleate))(8) was obtained. APCI-MS (Positive): 913 [M+H] + Metal composite (8) (700 mg) is used at 180°C and 3 x 10 -6 Sublimation was performed at mbar. The yield was 150 mg (22%). The metal complex (8) decomposes at 244°C. In cyclic voltammetry of 8 samples in acetonitrile (ACN, 200 mV / s, 0.1M NBu4PF6), the following results were obtained: E 1 / 2 (vs. Fc / Fc + ) = +0.08V. When ZnPc (zinc phthalocyanine) is doped with 20 wt% dopant (8), after co-deposition in a vacuum, a maximum of 7.6 x 10⁻¹⁶ particles are obtained.-5 Conductivity increases up to S / cm were measured. The intrinsic conductivity of undoped ZnPc is 1 x 10⁻¹⁰. -8 The ratio is less than S / cm (Tietze, ML, Pahner, P., Schmidt, K., Leo, K., & Lussem, B. (2015). Advanced Functional Materials, 25(18), 2701-2707). When MeO-TPD (CAS No.: 122738-21-0) is doped with 20 wt% dopant (8), after co-deposition in a vacuum, a maximum of 1 x 10⁻¹⁶ particles are deposited. -5 Conductivity increases up to S / cm were measured. The intrinsic conductivity of undoped ZnPc is 7 x 10⁻¹⁰. -8 S / cm (Sakai, N., Warren, R., Zhang, F., Nayak, S., Liu, J., Kesava, SV, Lin, Y.-H., Biswal, HS, Lin, X., Grovenor, C., Malinauskas, T., Basu, A., Anthopoulos, TD, Getautis, V., Kahn, A., Riede, M., Nayak, PK, & Snaith, HJ (2021). Adduct-based p-doping of organic semiconductors. Nature Materials 2021 20:9, 20(9), 1248-1254.). When spiro-MeO-TAD (CAS No.: 207739-72-8) is doped with 20 wt% dopant (8), after solvent treatment (rotary coating), a maximum of 2.8 x 10⁻¹⁰ units is obtained. -6 Conductivity increases up to S / cm were measured. The intrinsic conductivity of undoped spiro-MeO-TAD is 2 x 10⁻¹⁰. -8 It was measured to be S / cm.

[0094] Synthesis of 9: JPEG0007870555000038.jpg52771-(3-chloro-4-(trifluoromethyl)phenyl)-4,4,5,5-pentafluoropentane-1,3-dione (3.00 g, 8.13 mmol) was suspended in B(nBuO)3 (9.35 g, 40.7 mmol), and 1,2-diaminophenylene (0.88 g, 8.13 mmol) was added. After 15 minutes, the white solid was filtered off and washed with a small amount of hexane. A white solid of 2.2 g (4.79 mmol, 59%) of 1-((2-aminophenyl)amino)-1-(3-chloro-4-(trifluoromethyl)phenyl)-4,4,5,5-pentafluoropent-1-en-3-one was obtained. APCI-MS (positive): 459 [M+H] + 4-Ethoxy-1,1,1-trifluorobuto-3-en-2-one (0.73 g, 4.37 mmol) was dissolved in DCM, and 1-((2-aminophenyl)amino)-1-(3-chloro-4-(trifluoromethyl)phenyl)-4,4,5,5-pentafluoropento-1-en-3-one (2.0 g, 4.37 mmol) was added. The reaction mixture was stirred for 12 hours, and then the solvent was removed. The residue was dissolved in acetonitrile, followed by the addition of copper(II) acetate (1.5 g). Water was added to this dark green solution, and the solid was filtered off. The solid was purified by column chromatography (eluent: chloroform). The residue was treated with oxalic acid and EDTA, then with concentrated hydrochloric acid and chloroform, and the phases were separated. The organic phase was washed with saturated solutions of NaHCO3 and NaCl, and dried over Na2SO4. The solvent was removed. A white solid was obtained from 2.0 g (3.44 mmol, 79%) of 1-(3-chloro-4-(trifluoromethyl)phenyl)-4,4,5,5-pentafluoro-1-((2-((-4,4,4-trifluoro-3-oxobuto-1-en-1-yl)amino)phenyl)amino)pento-1-en-3-one. APCI-MS (positive): 581.8 [M+H] + 1-(3-chloro-4-(trifluoromethyl)phenyl)-4,4,5,5-pentafluoro-1-((2-((-4,4,4-trifluoro-3-oxobuto-1-en-1-yl)amino)phenyl)amino)pento-1-en-3-one (1.9 g, 3.2 mmol) was added to a solution of cerium(IV) isopropoxide (0.32 M DME / iPrOH solution, 1.63 mmol, 5.1 ml). Hexane was added, the resulting solid was filtered off, and washed with hexane. The residue was dissolved in chloroform, filtered, and recrystallized from chloroform / hexane. 0.41 g (0.316 mmol, 20%) of a red solid (9) was obtained. APCI-MS (positive): 1296.8 [M+H] + Metal composite (9) (313 mg) is suitable for use at 180-190°C and 3x10 -6 Sublimation was performed at mbar. The yield was 167 mg (53%). The metal complex (9) decomposes at 244°C. The following results were obtained from cyclic voltammetry of 9 samples in acetonitrile (ACN, 200 mV / s, 0.1M NBu4PF6): E 1 / 2 (vs. Fc / Fc + ) = +0,0V. When ZnPc (zinc phthalocyanine) is doped with 20 wt% dopant (9), a maximum of 1.1 x 10⁻¹⁰ ions can be deposited after co-deposition in a vacuum. -5 Conductivity increases up to S / cm were measured. The intrinsic conductivity of undoped ZnPc is 1 x 10⁻¹⁰. -8 The ratio is less than S / cm (Tietze, ML, Pahner, P., Schmidt, K., Leo, K., & Lussem, B. (2015). Advanced Functional Materials, 25(18), 2701-2707). When spiro-MeO-TAD (CAS No.: 207739-72-8) is doped with 20 wt% dopant (9), after solvent treatment (rotary coating), the maximum size is 5.1 x 10⁻¹⁰. -6 Conductivity increases up to S / cm were measured. The intrinsic conductivity of undoped spiro-MeO-TAD is 2 x 10⁻¹⁰.-8 It was measured to be S / cm.

Claims

1. An electronic component comprising at least one compound of general formula (I), Ce 4+ [L 1 L 2 ] 4- (I) In the formula, L 1 and L 2 However, each of them is a ligand in equation (I.1) A tetradentate ligand that is selected independently from, in the formula, X represents O; Z is a bridging group having 2 or 3 carbon atoms between nitrogen atoms, where each of the carbon atoms is unsubstituted or is substituted with 1, 2, 3, 4, 5, or 6 identical or different free radicals R 12 and where two adjacent carbon atoms may be linked to each other by a double bond or where 2 or 3 of the carbon atoms are part of a mononuclear, dinuclear, or trinuclear C 6 -C 14 aromatic or heteroaromatic ring system, where the heteroaromatic ring system has 4 to 13 carbon atoms and has 1, 2, or 3 identical or different heteroatoms or groups containing heteroatoms as ring members selected from N, NR 8 , O, S, SO, and SO 2 and where the aromatic or heteroaromatic ring system is unsubstituted or is substituted with 1, 2, 3, 4, or 5 identical or different free radicals R 9 ; A and B are independent of each other and are N or CR 7 It represents; R 1 and R 6 However, hydrogen, CN, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl, C 1 -C 6 Alkoxy, C 1 -C 6 Haloalkoxy, C 3 -C 7 Selected independently from cycloalkyl, where C 3 -C 7 The cycloalkyl group is either unsubstituted or has 1, 2, 3, 4, 5, or 6 identical or different free groups R 11 , C 1 -C 6 Alkyl sulfanyl, C 1 -C 6 Haloalkylsulfanil, NR 4a R 4b , C having 4 to 13 carbon atoms 6 -C 14 Replaced with aryl and hetalir, where hetalir is N, NR 8 O, S, SO, and SO 2 The ring members selected from have 1, 2, or 3 identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, 4, or 5 identical or different free groups R 9 Replaced by; R2 and R 5 However, hydrogen, CN, C 1 -C 6 Alkyl, C 1 -C 6 -Haloalkyl, C 1 -C 6 Alkoxy, C 1 -C 6 Haloalkoxy, C 3 -C 7 Selected independently from cycloalkyl, where C 3 -C 7 The cycloalkyl group is either unsubstituted or has 1, 2, 3, 4, 5, or 6 identical or different free groups R 11 , C 1 -C 6 Alkyl sulfanyl, C 1 -C 6 Haloalkylsulfanil, NR 4a R 4b , C having 4 to 13 carbon atoms 6 -C 14 Replaced with aryl and hetalir, where hetalir is N, NR 8 O, S, SO, and SO 2 The ring members selected from have 1, 2, or 3 identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, 4, or 5 identical or different free groups R 9 Replaced by; R 2 And A, along with the carbon atoms to which they are bonded, C 6 -C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 O, S, SO, and SO 2 The ring members selected from have 1, 2, or 3 identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have 1, 2, 3, or 4 identical or different free groups R 9 Replaced by, or R 5 And B, along with the carbon atoms to which they are bonded, C 6 -C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 O, S, SO, and SO 2 The ring members selected from have 1, 2, or 3 identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have 1, 2, 3, or 4 identical or different free groups R 9 Replaced by; R 4a R 4b However, hydrogen and C are independent of each other. 1 -C 6 Alkyl and C 6 -C 14 Selected from aryl groups, where the aryl group is unsubstituted or consists of 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 7 is hydrogen, CN, nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a R 4b , C having 4 to 13 carbon atoms 6 -C 14 aryl and heteroaryl selected from, where heteroaryl has 1, 2, or 3 identical or different heteroatoms or groups containing heteroatoms as ring members selected from N, NR 8 , O, S, SO, and SO 2 where aryl and heteroaryl are unsubstituted or substituted with 1, 2, 3, 4, or 5 identical or different free radicals R 10 ; R 8 However, hydrogen, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl and C 6 -C 14 Selected from aryls, where the aryl is unsubstituted or consists of 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 9 However, CN, halogen, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl and C 6 -C 14 Selected from aryls, where the aryl is either unsubstituted or C 1 -C 4 Alkyl and C 1 -C 4 Substituted with one, two, three, four, or five identical or different free radicals selected from haloalkyl groups; R 10 However, CN, halogen, C 1 -C 4 Alkyl, C 1 -C 4 Selected from haloalkyls; R 11 However, CN, halogen, C 1 -C 4 Alkyl, C 1 -C 4 Selected from haloalkyls; R 12 However, halogen, CN, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl, C 1 -C 6 Alkoxy, C 1 -C 6 Haloalkoxy, C 3 -C 7 Selected independently from cycloalkyl, where C 3 -C 7 The cycloalkyl group is either unsubstituted or has 1, 2, 3, 4, 5, or 6 identical or different free groups R 11 , C 1 -C 6 Alkyl sulfanyl, C 1 -C 6 Haloalkylsulfanil, NR 4a R 4b , C having 4 to 13 carbon atoms 6 -C 14 Replaced with aryl and hetalir, where hetalir is N, NR 8 O, S, SO, and SO 2 The ring members selected from have 1, 2, or 3 identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, 4, or 5 identical or different free groups R 9 Replaced by, electronic component.

2. at least one compound of general formula (I) What 4+ [IT 1 IT 2 ] 4- (I) (In the formula, L 1 and L 2 However, each of them is a ligand in equation (II) A tetradentate ligand that is selected independently from, in the formula, CR 3 Base and CR 4 Between However, it represents a single bond or a double bond; X represents O; A and B are independent of each other and are N or CR 7 It represents; R 1 and R 6 However, hydrogen, CN, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl, C 1 -C 6 Alkoxy, C 1 -C 6 Haloalkoxy, C 1 -C 6 Alkyl sulfanyl, C 1 -C 6 Haloalkylsulfanil, NR 4a R 4b , C having 4 to 13 carbon atoms 6 -C 14 Selected independently from aryl and hetalir, where hetalir is N, NR 8 O, S, SO, and SO 2 The ring members selected from have 1, 2, or 3 identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, 4, or 5 identical or different free groups R 9 Replaced by; R 3 and R 4 However, hydrogen, CN, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl, C 1 -C 6 Alkoxy, C 1 -C 6 Haloalkoxy, C 1 -C 6 Alkyl sulfanyl, C 1 -C 6 Haloalkylsulfanil, NR 4a R 4b , C having 4 to 13 carbon atoms 6 -C 14 Selected independently from aryl and hetalir, where hetalir is N, NR 8 O, S, SO, and SO 2 The ring members selected from have 1, 2, or 3 identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, 4, or 5 identical or different free groups R 9 Replaced by, or R 3 and R 4 However, along with the carbon atoms to which they are bonded, C 6 -C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 O, S, SO, and SO 2 The ring members selected from have 1, 2, or 3 identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have 1, 2, 3, or 4 identical or different free groups R 9 Replaced by; R 2 and R 5 However, hydrogen, CN, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl, C 1 -C 6 Alkoxy, C 1 -C 6 Haloalkoxy, C 1 -C 6 Alkyl sulfanyl, C 1 -C 6 Haloalkylsulfanil, NR 4a R 4b , C having 4 to 13 carbon atoms 6 -C 14 Selected independently from aryl and hetalir, where hetalir is N, NR 8 O, S, SO, and SO 2 The ring members selected from have 1, 2, or 3 identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, 4, or 5 identical or different free groups R 9 Replaced by; R 4a R 4b However, hydrogen and C are independent of each other. 1 -C 6 Alkyl and C 6 -C 14 Selected from aryl groups, where the aryl group is unsubstituted or consists of 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 7 However, hydrogen, CN, nitro, halogen, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl, C 1 -C 6 Alkoxy, C 1 -C 6 Haloalkoxy, C 1 -C 6 Alkyl sulfanyl, C 1 -C 6 Haloalkylsulfanil, NR 4a R 4b , C having 4 to 13 carbon atoms 6 -C 14 Selected from aryl and hetalir, where hetalir is N, NR 8 O, S, SO, and SO 2 The ring members selected from have 1, 2, or 3 identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 8 However, hydrogen, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl and C 6 -C 14 Selected from aryl groups; where the aryl group is unsubstituted or consists of 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 9 However, CN, halogen, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl and C 6 -C 14 Selected from aryls; where aryl is unsubstituted or C 1 -C 4 Alkyl and C 1 -C 4 Substituted with one, two, three, four, or five identical or different free radicals selected from haloalkyl groups; R 10 However, CN, halogen, C 1 -C 4 Alkyl, C 1 -C 4 (Selected from haloalkyls) The electronic component according to claim 1, including the electronic component described in claim 1.

3. In equation (I.1) or equation (II), R 1 , R 2 , R 5 , and R 6 However, hydrogen, CN, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl, C 1 -C 6 Alkoxy, C 1 -C 6 Haloalkoxy, C 1 -C 6 Alkyl sulfanyl, C 1 -C 6 Haloalkylsulfanil, NR 4a R 4b , and base A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, and A19 (Here, # indicates a bond to the base of formula (I), and here R A , R B , R C , R D , and R E However, hydrogen, CN, halogen, C 1 -C 4 Alkyl and C 1 -C 4 Selected independently from haloalkyl groups; R 4a and R 4b However, hydrogen, C 1 -C 6 Alkyl and C 6 -C 14 A free group R is independently selected from the aryl group, where the aryl group is either unsubstituted or consists of 1, 2, 3, 4, or 5 identical or different free groups. 10 Replaced by; R 9 However, CN, halogen, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl and C 6 -C 14 Selected from aryls, where the aryl is either unsubstituted or C 1 -C 4 Alkyl and C 1 -C 4 Substituted with one, two, three, four, or five identical or different free radicals selected from haloalkyl groups; also, R 10 However, CN, halogen, C 1 -C 4 Alkyl and C 1 -C 4 (Selected from haloalkyls) An electronic component according to claim 1 or 2, independently selected from the above.

4. In equation (II), R 2 and R 5 However, hydrogen, CN, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl, C 1 -C 6 Alkoxy, C 1 -C 6 A haloalkoxy and phenyl are independently selected, where phenyl is unsubstituted or has 1, 2, 3, or 4 identical or different free groups R 9 Replaced by, or R 3 and R 4 However, along with the carbon atoms to which they are bonded, C 6 -C 14 An aryl group is formed, where the aryl is unsubstituted or consists of 1, 2, 3, or 4 identical or different free groups R 9 Replaced by; R 9 However, CN, halogen, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl and C 6 -C 14 Selected from aryls; where aryl is unsubstituted or C 1 -C 4 Alkyl or C 1 -C 4 Substituted with 1, 2, 3, 4, or 5 identical or different free radicals selected from haloalkyl groups. The electronic component according to any one of claims 1 to 3.

5. In formula (I.1) or formula (II), A and B are independent free radicals CR 7 And also, R 7 However, the group B consists of hydrogen, CN, nitro, halogen, and B1, B2, B3, B4, B5, B6, B7, B8, B9, B10, B11, B12, B13, B14, and B15. (In the formula, # indicates bonding to the base of formula (II), and R F , R G , R H , R I , and R J However, hydrogen, CN, halogen, C 1 -C 4 Alkyl and C 1 -C 4 An electronic component according to any one of claims 1 to 4, selected from (independently selected from haloalkyl).

6. In equation (I.1) or equation (II), R 1 , R 2 , R 5 , and R 6 However, hydrogen, C 1 -C 4 Alkyl, C 1 -C 4 Haloalkyl and A1 (# indicates a bond to the rest of the numerator of formula (I.1) or formula (II), where R A , R B , R C , R D , and R E However, hydrogen, CN, fluorine, chlorine, C 1 -C 4 Alkyl, C 1 -C 4 Fluoroalkyl, and C 1 -C 4 Selected independently from chloroalkyl, R 9 is CN, halogen, C 1 -C 4 Alkyl, C 1 -C 4 Selected from haloalkyl and phenyl, where phenyl is unsubstituted or C 1 -C 4 Alkyl or C 1 -C 4 An electronic component according to any one of claims 1 to 5, independently selected from (substituted with 1, 2, 3, 4, or 5 identical or different substituents selected from haloalkyl groups).

7. In formula (I.1) or formula (II), an independent free radical CR 7 And R 7 However, hydrogen, CN, nitro, halogen, C 1 -C 2 Alkyl and C 1 -C 2 An electronic component according to any one of claims 1 to 6, selected from haloalkyls.

8. R 3 and R 4 However, hydrogen, CN, C 1 -C 4 Alkyl, C 1 -C 4 Independently selected from haloalkyl groups, or R 3 and R 4 However, together with the carbon atoms to which they are bonded, they form a phenyl ring, where phenyl is either unsubstituted or has 1, 2, 3, or 4 identical or different free radicals R 9 Replaced by; R 9 However, CN, halogen, C 1 -C 4 Alkyl, C 1 -C 4 Selected from haloalkyl or phenyl; where phenyl is unsubstituted or C 1 -C 4 Alkyl or C 1 -C 4 Substituted with 1, 2, 3, or 4 identical or different substituents selected from haloalkyl groups. The electronic component according to any one of claims 1 to 7.

9. L 1 and L 2 However, the electronic component described in any one of claims 1 to 8 has the same meaning.

10. An electronic component according to any one of claims 1 to 9, in the form of an organic light-emitting diode, an organic solar cell, a solar cell, an organic sensor, an organic diode, or an organic field-effect transistor.

11. The electronic component according to any one of claims 1 to 10, having a layer structure comprising two, three, four, five, six, seven, or more layers.

12. The electronic component according to any one of claims 1 to 11, comprising a vacancy transport layer and / or a vacancy injection layer containing at least a compound of formula (I).

13. The electronic component according to any one of claims 1 to 12, comprising an electron transport layer containing at least a compound of formula (I).

14. A doped semiconductor matrix material comprising at least one electron donor and at least one compound of formula (I) as defined in any of claims 1 to 9, wherein the electron donor is 4,4',4"-tris(N-(2-naphthyl)-N-phenyl-amino)triphenylamine(2-TNATA), 4,4',4"-tris(N-3-methylphenyl-N-phenyl)-amino)triphenylamine(m- MTDATA), N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine (MeO-TPD), (2,2',7,7'-tetrakis-(N,N-diphenylamino)-9,9'-spirobifluorene (Spiro-TTB), N,N'-bis(naphthalene-1-yl)-N,N'-bis(phenyl)-benzidine, N,N'-bis(naphthalene-1-yl)-N,N'-bis(phenyl)-9,9-s Pyrobifluorene, 9,9-bis[4-(N,N-bis-biphenyl-4-yl-amino)phenyl]-9H-fluorene, 2,2'-bis[N,N-bis(biphenyl-4-yl)amino]-9,9-spirobifluorene, N,N'-((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine)( BPAPF), N,N'-bis(phenanthrene-9-yl)-N,N'-bis(phenyl)-benzidine, 1,3,5-tris{4-[bis(9,9-dimethyl-fluoren-2-yl)amino]phenyl}benzene, tri(terphenyl-4-yl)amine, N-(4-(6-((9,9-dimethyl-9H-fluoren-2-yl)(6-methoxy-[1,1'-biphenyl]-3-yl)amino)-1,3,3 -Trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(6-methoxy-[1,1'-biphenyl]-3-yl)-9,9-dimethyl-9H-fluoren-2-amine, N-([1,1'-biphenyl]-4-yl)-N-(4-(6-([1,1'-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine, N,N-di([1,1'-biphenyl]-4-yl)-3-(4-(di([1,1'-biphenyl]-4-yl)amino)phenyl)-1,1,3-trimethyl-2,3-dihydro-1H-inden-5-amine, N-(4-(6-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine, N-(4-(6-(9,9'-spirobio[fluoren]-2-yl) (9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio[fluorene]-2-amine, N-(4-(6-(dibenzo[b,d]furan-2-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3)-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b ,d]furan-2-amine, 9-(4-(6-(9H-carbazole-9-yl)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-9H-carbazole, N-([1,1'-biphenyl]-4-yl)-3-(4-([1,1'-biphenyl]-4-yl(4-methoxyphenyl)amino)phenyl)-N-(4-methoxyphenyl)-1,1,3-trimethyl-2,3-dihydro-1H-inden-5-amine, 3-(4-(bis(6-methoxy-[1,1'-biphenyl]-3-yl)amino)phenyl )-N,N-bis(6-methoxy-[1,1'-biphenyl]-3-yl)-1,1,3-trimethyl-2,3-dihydro-1H-inden-5-amine, N1-([1,1'-biphenyl]-4-yl)-N1-(4-(6-([1,1'-biphenyl]-4-yl(4-(diphenylamino)phenyl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, N,N-di([1,1'-biphenyl]-4-yl)-4'-(6-(4-(di([1,1'-biphenyl]-4-yl)amino)phenyl)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)-[1,1'-biphenyl]-4-amine, N-(4-(5-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine, N-(4-(6-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-yl Nden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine, N,N'-bis(9,9-dimethyl-fluoren-2-yl)-N,N'-diphenyl-benzidine (BF-DPB), N,N'-((9H-fluoren-9,9-diyl)bis(4,1-phenylene))bis(N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine)(BPAPF), N4,N4,N4',N4'-tetrakis(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-4,4'-diamine (TDMFB), N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio[fluoren]-2-amine, (2,7-bis[N,N-bis(4-methoxyphenyl)amino]-9,9-spirobio[9H-fluoren](spiro-MeO-TPD), N-(4-(5-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl) A mixture of phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine and N-(4-(6-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine, N-([1,1'-biphenyl]-4-yl)-9,A semiconductor matrix material selected from 9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluoren-2-amine and mixtures thereof.

15. A compound of formula (I) or a mixture thereof as defined in any of claims 1 to 9, — As an organic semiconductor, —As a doping agent in organic semiconductor matrix materials —As a p-dopant in the vacancy transport layer, — As a charge injector in the charge injection layer, — As an electron transport layer, — As a cathode material in organic batteries, — As an electrochromic material, — As an electron acceptor Use.

16. Compounds of general formula (I) What 4+ [IT 1 IT 2 ] 4- (I) (In the formula, L 1 and L 2 However, each of them is a ligand in equation (I.1) A tetradentate ligand that is selected independently from, in the formula, X represents O; Z is a bridging group having two or three carbon atoms between nitrogen atoms, where each carbon atom is either unsubstituted or one, two, three, four, five, or six identical or different free groups R 12 Substituted with, where two adjacent carbon atoms may be linked to each other by a double bond, or two or three of the carbon atoms may be mononuclear, dinuclear, or trinuclear C 6 -C 14 It is part of an aromatic or heteroaromatic ring system, where the heteroaromatic ring system has 4 to 13 carbon atoms, and also contains N, NR 8 O, S, SO, and SO 2 The ring member selected from has 1, 2, or 3 identical or different heteroatoms or groups containing heteroatoms, where the aromatic or heteroaromatic ring system is unsubstituted or has 1, 2, 3, 4, or 5 identical or different free groups R 9 Replaced by; A and B are independent of each other and are N or CR 7 It represents; R 1 and R 6 However, hydrogen, CN, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl, C 1 -C 6 Alkoxy, C 1 -C 6 Haloalkoxy, C 3 -C 7 Selected independently from cycloalkyl, where C 3 -C 7 The cycloalkyl group is either unsubstituted or has 1, 2, 3, 4, 5, or 6 identical or different free groups R 11 , C 1 -C 6 Alkyl sulfanyl, C 1 -C 6 Haloalkylsulfanil, NR 4a R 4b , C having 4 to 13 carbon atoms 6 -C 14 Replaced with aryl and hetalir, where hetalir is N, NR 8 O, S, SO, and SO 2 The ring members selected from have 1, 2, or 3 identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, 4, or 5 identical or different free groups R 9 Replaced by; R2 and R 5 However, hydrogen, CN, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl, C 1 -C 6 Alkoxy, C 1 -C 6 Haloalkoxy, C 3 -C 7 Selected independently from cycloalkyl, where C 3 -C 7 The cycloalkyl group is either unsubstituted or has 1, 2, 3, 4, 5, or 6 identical or different free groups R 11 , C 1 -C 6 Alkyl sulfanyl, C 1 -C 6 Haloalkylsulfanil, NR 4a R 4b , C having 4 to 13 carbon atoms 6 -C 14 Replaced with aryl and hetalir, where hetalir is N, NR 8 O, S, SO, and SO 2 The ring members selected from have 1, 2, or 3 identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, 4, or 5 identical or different free groups R 9 Replaced by; R 2 And A, along with the carbon atoms to which they are bonded, C 6 -C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 O, S, SO, and SO 2 The ring members selected from have 1, 2, or 3 identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have 1, 2, 3, or 4 identical or different free groups R 9 Replaced by, or R 5 And B, along with the carbon atoms to which they are bonded, C 6 -C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 O, S, SO, and SO 2 The ring members selected from have 1, 2, or 3 identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have 1, 2, 3, or 4 identical or different free groups R 9 Replaced by; R 4a R 4b However, hydrogen and C are independent of each other. 1 -C 6 Alkyl and C 6 -C 14 Selected from aryl groups, where the aryl group is unsubstituted or consists of 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 7 However, hydrogen, CN, nitro, halogen, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl, C 1 -C 6 Alkoxy, C 1 -C 6 Haloalkoxy, C 1 -C 6 Alkyl sulfanyl, C 1 -C 6 Haloalkylsulfanil, NR 4a R 4b , C having 4 to 13 carbon atoms 6 -C 14 Selected from aryl and hetalir, where hetalir is N, NR 8 O, S, SO, and SO 2 The ring members selected from have 1, 2, or 3 identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 8 However, hydrogen, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl and C 6 -C 14 Selected from aryls, where the aryl is unsubstituted or consists of 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 9 However, CN, halogen, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl and C 6 -C 14 Selected from aryls, where the aryl is either unsubstituted or C 1 -C 4 Alkyl and C 1 -C 4 Substituted with one, two, three, four, or five identical or different free radicals selected from haloalkyl groups; R 10 However, CN, halogen, C 1 -C 4 Alkyl, C 1 -C 4 Selected from haloalkyls; R 11 However, CN, halogen, C 1 -C 4 Alkyl, C 1 -C 4 Selected from haloalkyls; R 12 However, halogen, CN, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl, C 1 -C 6 Alkoxy, C 1 -C 6 Haloalkoxy, C 3 -C 7 Selected independently from cycloalkyl, where C 3 -C 7 The cycloalkyl group is either unsubstituted or has 1, 2, 3, 4, 5, or 6 identical or different free groups R 11 , C 1 -C 6 Alkyl sulfanyl, C 1 -C 6 Haloalkylsulfanil, NR 4a R 4b , C having 4 to 13 carbon atoms 6 -C 14 Replaced with aryl and hetalir, where hetalir is N, NR 8 O, S, SO, and SO 2 The ring members selected from have 1, 2, or 3 identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, 4, or 5 identical or different free groups R 9 Replaced by; However, the following compounds: (However, it is excluded.) Those charge transfer complexes, their reduced products, and mixtures thereof.

17. The compound of general formula (I) described in claim 16 What 4+ [IT 1 IT 2 ] 4- (I) (In the formula, L 1 and L 2 However, each of them is a ligand in equation (II) A tetradentate ligand that is selected independently from, in the formula, CR 3 Base and CR 4 Between However, it represents a single bond or a double bond; X represents O; A and B are independent of each other and are N or CR 7 It represents; R 1 and R 6 However, hydrogen, CN, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl, C 1 -C 6 Alkoxy, C 1 -C 6 Haloalkoxy, C 1 -C 6 Alkyl sulfanyl, C 1 -C 6 Haloalkylsulfanil, NR 4a R 4b , C having 4 to 13 carbon atoms 6 -C 14 Selected independently from aryl and hetalir, where hetalir is N, NR 8 O, S, SO, and SO 2 The ring members selected from have 1, 2, or 3 identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, 4, or 5 identical or different free groups R 9 Replaced by; R 3 and R 4 However, hydrogen, CN, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl, C 1 -C 6 Alkoxy, C 1 -C 6 Haloalkoxy, C 1 -C 6 Alkyl sulfanyl, C 1 -C 6 Haloalkylsulfanil, NR 4a R 4b , C having 4 to 13 carbon atoms 6 -C 14 Selected independently from aryl and hetalir, where hetalir is N, NR 8 O, S, SO, and SO 2 The ring members selected from have 1, 2, or 3 identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, 4, or 5 identical or different free groups R 9 Replaced by, or R 3 and R 4 However, along with the carbon atoms to which they are bonded, C 6 -C 14 It forms an aryl group or a hetalil group having 4 to 13 carbon atoms, where the hetalil is N,NR 8 O, S, SO, and SO 2 The ring members selected from have 1, 2, or 3 identical or different heteroatoms or heteroatom-containing groups, and the aryl and hetalil are unsubstituted or have 1, 2, 3, or 4 identical or different free groups R 9 Replaced by; R 2 and R 5 However, hydrogen, CN, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl, C 1 -C 6 Alkoxy, C 1 -C 6 Haloalkoxy, C 1 -C 6 Alkyl sulfanyl, C 1 -C 6 Haloalkylsulfanil, NR 4a R 4b , C 6 -C 14 Independently selected from aryls and hetalirs having 4 to 13 carbon atoms, where the hetalir is N, NR 8 O, S, SO, and SO 2 The ring members selected from have 1, 2, or 3 identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, 4, or 5 identical or different free groups R 9 Replaced by; R 4a R 4b However, hydrogen and C are independent of each other. 1 -C 6 Alkyl and C 6 -C 14 Selected from aryl groups, where the aryl group is unsubstituted or consists of 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 7 However, hydrogen, CN, nitro, halogen, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl, C 1 -C 6 Alkoxy, C 1 -C 6 Haloalkoxy, C 1 -C 6 Alkyl sulfanyl, C 1 -C 6 Haloalkylsulfanil, NR 4a R 4b , C 6 -C 14 Selected from aryls and hetalyrs having 4 to 13 carbon atoms, where the hetalyr is N, NR 8 O, S, SO, and SO 2 The ring members selected from have 1, 2, or 3 identical or different heteroatoms or heteroatom-containing groups, where the aryl and hetalil are unsubstituted or 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 8 However, hydrogen, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl and C 6 -C 14 Selected from aryl groups; where the aryl group is unsubstituted or consists of 1, 2, 3, 4, or 5 identical or different free groups R 10 Replaced by; R 9 However, CN, halogen, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl and C 6 -C 14 Selected from aryls; where aryl is unsubstituted or C 1 -C 4 Alkyl and C 1 -C 4 Substituted with one, two, three, four, or five identical or different free radicals selected from haloalkyl groups; R 10 However, CN, halogen, C 1 -C 4 Alkyl, C 1 -C 4 Selected from haloalkyls, However, the compound of the following formula (I): L 1 = L 2 = N,N'-bis(4,4,4,-trifluorobuto-1-en-3-one)-ethylenediamine, L 1 = L 2 = N,N'-bis(4,4,5,5,5-pentafluoropento-1-en-3-one)-ethylenediamine, L 1 = L 2 = N,N'-bis(4,4,5,5,6,6,6-heptafluorohex-1-en-3-one)-ethylenediamine, And their reaction products are excluded, as well as the following compounds: (and their reaction products are excluded.) Those charge transfer complexes, their reduced products, and mixtures thereof.

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