CN114907361A - Trimeric heterocyclic derivative and application thereof - Google Patents
Trimeric heterocyclic derivative and application thereof Download PDFInfo
- Publication number
- CN114907361A CN114907361A CN202210631893.4A CN202210631893A CN114907361A CN 114907361 A CN114907361 A CN 114907361A CN 202210631893 A CN202210631893 A CN 202210631893A CN 114907361 A CN114907361 A CN 114907361A
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- trimeric
- heterocyclic derivative
- organic
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/16—Peri-condensed systems
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/14—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/16—Peri-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/16—Peri-condensed systems
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
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Abstract
The invention relates to a trimeric heterocyclic derivativeThe structural general formula of the trimeric heterocyclic derivative is shown as a formula (I), and the trimeric heterocyclic derivative is suitable for electronic elements, particularly organic electroluminescent devices and organic solar cells, and relates to organic electroluminescent devices, organic solar cell devices and electronic equipment containing the trimeric heterocyclic derivative. The trimeric heterocyclic derivative provided by the invention has very high efficiency and long service life when used as a carrier material.
Description
Technical Field
The invention belongs to the technical field of organic electronic materials, and particularly relates to a trimeric heterocyclic derivative, an electronic material containing the trimeric heterocyclic derivative and an electronic element containing the trimeric heterocyclic derivative.
Background
The acceptor materials of the organic solar cell are mainly classified into fullerene acceptor and non-fullerene acceptor materials. Due to some defects of the fullerene acceptor material, such as narrow absorption spectrum, difficult energy level regulation, limited structural flexibility and the like, the further improvement of the efficiency of the organic solar cell is limited. And the non-fullerene acceptor material overcomes the defects of the fullerene acceptor material and is widely researched in the application of the organic solar cell. However, the existing non-fullerene fused ring electron acceptor material still has the problems of narrow absorption range, wide optical band gap, low mobility and the like.
In recent years, organic solar cells and organic electroluminescent display technologies have become mature, some products have already entered the market, but many problems still need to be solved in the industrialization process. In particular, various organic materials used for manufacturing devices have problems such as carrier injection and transport performance, photoelectric performance of the materials, service life, matching between various materials and between various electrodes, and the like, which have not yet been solved. Especially, organic materials having n-type characteristics as electron injection materials or electron transport materials have greatly limited the development of organic photovoltaic technologies.
The present invention has been made in view of the above circumstances.
Disclosure of Invention
In order to solve the above problems in the prior art, the present invention provides a trimeric heterocyclic compound, and an electronic material and an electronic component comprising the same, wherein the trimeric heterocyclic compound is suitable for use in an OLED or an OPV, and has high thermal stability and high mobility.
The first object of the present invention is to provide a trimeric heterocyclic compound, which has a general structural formula shown in formula (I):
wherein, X 1 、X 2 、X 3 Each independently selected from O, S, SO 2 、SiR 7 R 8 、BR 7 、NR 8 、PR 7 Or POR 8 ；
R 1 、R 2 、R 3 、R 4 、R 5 、R 6 Each independently selected from the group consisting of fluorine, nitrile, having C 1 ～C 40 Straight chain alkyl of (2) having C 3 ～C 40 A branched or cyclic alkyl group having C 1 ～C 40 Linear heteroalkyl group of (A) having C 3 ～C 40 A branched or cyclic heteroalkyl group of (2), substituted or unsubstituted C 6 ～C 60 Arylboron group of (A), substituted or unsubstituted C 6 ～C 60 Aryl of (A), substituted or unsubstituted C 6 ～C 60 Aryl silicon group, substituted or unsubstituted C 2 ～C 60 Of R, R 1 And R 2 、R 3 And R 4 Or R 5 And R 6 May be optionally joined or fused to form a substituted or unsubstituted ring, and R 1 、R 2 、R 3 、R 4 、R 5 、R 6 Optionally substituted by fluorine atoms or nitrile groupsReplacing;
R 7 、R 8 each independently selected from the group consisting of 1 ～C 40 Straight chain alkyl of (2) having C 3 ～C 40 A branched or cyclic alkyl group having C 6 ～C 60 Or have C 2 ～C 60 And R is 7 、R 8 Optionally substituted with fluorine atoms or nitrile groups.
Further, the trimeric heterocyclic derivative is selected from the group consisting of structures represented by formulae (1) to (62):
aryl in the sense of the present invention contains 6 to 60 carbon atoms; heteroaryl in the sense of the present invention contains 2 to 60 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5, said heteroatom being preferably N, O or S. Aryl or heteroaryl herein is considered to mean a simple aromatic ring, i.e., benzene, naphthalene, etc., or a simple heteroaromatic ring, e.g., pyridine, pyrimidine, thiophene, etc.; or a fused aryl or heteroaryl group such as anthracene, phenanthrene, triphenylene, quinoline, isoquinoline, anthradine, and the like; or from simple aryl groups such as benzene, naphthalene, phenanthrene, pyridine, etc., or combinations of these groups, with one or more non-aromatic units such as C, N, O or an S atom, for example, as in systems where two or more aryl groups are linked by, for example, a short alkyl group, such as fluorene, 9' -spirobifluorene, 9-diarylfluorene, carbazole, diaryl ether, dibenzofuran, dibenzothiophene, etc.
According to an embodiment of the invention, said C 2 ～C 60 The heteroaryl group of (a) is selected from the group consisting of the structures represented by formulae (63) to (81):
according to an embodiment of the invention, said C 6 ～C 60 The aryl group of (a) is a group consisting of the structures represented by formulae (82) to (100):
wherein the dashed bond indicates the position at which the substituent is attached;
T 1 selected from O, S, NR or Si (R) 2 ；
R is selected, identically or differently on each occurrence, from the group consisting of hydrogen atom, deuterium atom, fluorine, chlorine, nitrile group, nitro group, trifluoromethyl group, trifluoroethyl group, trifluoromethoxy group, pentafluoroethyl group, pentafluoroethoxy group, trifluoroacetyl group, trifluoromethylthio group, pentafluorothio group, compounds having C 1 ～C 40 Straight chain alkyl of (2) having C 3 ～C 40 A branched or cyclic alkyl group having C 6 ～C 60 Or have C 2 ～C 60 Heteroaryl group of (a).
According to an embodiment of the invention, said R is selected from the group consisting of hydrogen, fluoro, chloro, nitrile, nitro, trifluoromethyl, trifluoroethyl, trifluoromethoxy, pentafluoroethyl, pentafluoroethoxy, trifluoroacetyl, trifluoromethylthio, pentafluorothio.
According to an embodiment of the present invention, said R 1 、R 2 、R 3 、R 4 、R 5 、R 6 Each independently selected from the group consisting of fluorine, chlorine, nitrile, trifluoromethyl, trifluoroethyl, trifluoromethoxy, pentafluoroethyl, pentafluoroethoxy, trifluoroacetyl, trifluoromethylthio, pentafluorothio, pyridyl, pyrimidinyl, triazinyl, 2, 6-dimethyl-1, 3, 5-triazinyl, 2, 6-bis (trifluoromethyl) -1, 3, 5-triazinyl, fluorophenyl, difluorophenyl, trifluorophenyl, tetrafluorophenyl, pentafluorophenyl, cyanophenyl, nitrilotrifluorophenyl, trifluoromethoxyphenyl, and the likeTrifluoromethoxyphenyl, trifluoromethoxydifluorophenyl, trifluoromethoxytrifluorophenyl, trifluoromethoxytetrafluorophenyl, trifluoromethylphenyl, trifluoromethylfluorophenyl, trifluoromethyldifluorophenyl, trifluoromethyltrifluorophenylphenyl, pentafluoroethylphenyl, pentafluoroethoxyphenyl, nitrophenyl, methylsulfonylphenyl, trifluoromethylsulfonylphenyl, trifluoromethylthiophenyl, pentafluorophenylthio, fluoropyridyl, difluoropyridinyl, trifluoropyridinyl, tetrafluoropyridinyl, R 1 And R 2 、R 3 And R 4 Or R 5 And R 6 May be optionally joined or fused to form a substituted or unsubstituted ring;
R 7 、R 8 each independently selected from the group consisting of methyl, nitrile, trifluoromethyl, trifluoroethyl, pentafluoroethyl, acetonitrile, difluoroacetonitrile, pyridyl, pyrimidyl, triazinyl, 2, 6-dimethyl-1, 3, 5-triazinyl, 2, 6-bis (trifluoromethyl) -1, 3, 5-triazinyl, fluorophenyl, difluorophenyl, trifluorophenyl, tetrafluorophenyl, pentafluorophenyl, cyanophenyl, nitrilodiphenyl, nitrilotrifluorophenyl, trifluoromethoxyphenyl, trifluoromethoxyfluorophenyl, trifluoromethoxydifluorophenyl, trifluoromethoxytrifluorophenyl, trifluoromethoxytetrafluorotetrafluorophenyl, trifluoromethylphenyl, trifluoromethylfluorophenyl, trifluoromethyldifluorophenyl, trifluoromethyltrifluorophenyl, trifluoromethyltetrafluorophenyl, pentafluoroethylphenyl, pentafluoroethoxyphenyl, pentafluoroethyl, thioethyl, thiobutyl, Nitrophenyl, methylsulfonylphenyl, trifluoromethylsulfonylphenyl, trifluoromethylthiophenyl, pentafluorophenylthio, fluoropyridyl, difluoropyridinyl, trifluoropyridinyl, tetrafluoropyridinyl.
According to an embodiment of the present invention, the trimeric heterocyclic derivative is selected from the group consisting of the structures shown below:
in the sense of the inventionThe alkyl group contains 1 to 40 carbon atoms and wherein the hydrogen atom or-CH is independently 2 Aliphatic hydrocarbon radicals whose radicals may also be substituted by the radicals R mentioned above, are preferably taken to mean the following radicals: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl, methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, sec-pentyloxy, 2-methylbutyloxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2, 2-trifluoroethoxy group. The heteroalkyl group is preferably an alkyl group having 1 to 40 carbon atoms, meaning a hydrogen atom or-CH alone 2 The radicals which may be substituted by oxygen, sulfur or halogen atoms are understood to mean alkoxy, alkylthio, fluorinated alkoxy, fluorinated alkylthio, in particular methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2, 2-trifluoroethoxy, 2,2, 2-trifluoroethylthio, vinyloxy, vinylthio, propenyloxy, propenylthio, butenylthio, butenyloxy, pentenyloxy, pentenylthio, cyclopentenyloxy, hexenyloxy, hexenylthio, cyclohexenyloxy, cyclohexenylthio, ethynyloxy, propenylthio, butenyloxy, pentenyloxy, cyclopentenyloxy, hexenyloxy, hexenylthio, cyclohexenyloxy, cyclohexenylthio, ethynyloxy, Ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio, hexynyloxy, hexynylthio.
In general, the cycloalkyl, cycloalkenyl groups according to the invention can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopenteneYl, cyclohexenyl, cycloheptyl, cycloheptenyl, wherein one or more-CH 2 The radicals may be replaced by the radicals mentioned above; furthermore, one or more hydrogen atoms may also be replaced by deuterium atoms, halogen atoms, or nitrile groups.
The alkenyl or alkynyl group according to the present invention has 2 to 40 carbon atoms, and the alkenyl or alkynyl group in which individual hydrogen atoms may be substituted by the above-mentioned group R is preferably an ethenyl group, a propenyl group, a butenyl group, an isobutenyl group, a styryl group, a distyryl group, an ethynyl group, a propynyl group, a butynyl group, a phenylethynyl group; furthermore, one or more hydrogen atoms may also be replaced by deuterium atoms, halogen atoms, or nitrile groups.
The present inventors have found through extensive experiments that the trimeric heterocyclic derivative gives rise to significant improvements in organic electroluminescent elements, particularly in terms of lifetime, efficiency and operating voltage. In particular, the compound of the present invention is used as an electron transporting material, and this case is applicable to phosphorescent and fluorescent electroluminescent elements. The trimeric heterocyclic derivative of the invention shows high photoelectric conversion efficiency and longer service life when used as an electron acceptor material of an organic solar cell. The materials generally have high redox stability, and the invention therefore relates to these materials and to electronic components comprising compounds of this type.
The invention also provides an organic electronic material, which comprises the application of the trimeric heterocyclic derivative in the photoelectric field of flexible transparent display, transparent thin film, optical communication or solar cell.
Preferably, the organic electroluminescent material and the organic solar cell material comprise the material of the trimeric heterocyclic derivative of the invention, and have carrier transport capability.
The third object of the present invention is to provide an organic electroluminescent device, comprising a first electrode, a second electrode, a capping layer (CPL layer for short), and at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers or the CPL layer comprises the trimeric heterocyclic derivative.
Preferably, the electron transport layer or CPL layer of the organic electroluminescent element comprises the trimeric heterocyclic derivative.
In this case, the above-mentioned tricyclic heterocyclic derivatives may be used alone or in combination of two or more.
The one or more organic layers may be any one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, and an electron injection layer. Preferably, the organic layer containing the compound of formula (I) may be a CPL layer, a light emitting layer, a hole injection layer, an electron transport layer, and more preferably, may be an electron transport layer or a hole injection layer.
The light-emitting layer of the organic electroluminescent element according to the present invention may contain a host material, preferably a phosphorescent host material, and in this case, the compound of the above chemical formula (I) may be contained as the host material. In the case where the light-emitting layer contains the compound represented by the above chemical formula (I), the electron transport ability is increased, and the binding force between holes and electrons in the light-emitting layer is increased, so that an organic electroluminescent element having excellent efficiency (light-emitting efficiency and power efficiency), life, luminance, driving voltage, and the like can be provided. The light-emitting layer dopant of the organic electroluminescent element of the present invention may contain the compound of the formula (I) or may contain other compounds as dopants.
The hole injection layer of the organic electroluminescent element of the present invention may contain a hole material, and in this case, the compound of the above chemical formula (I) may be contained as the hole injection material. In the case where the hole injection layer includes the compound represented by the above chemical formula (I), the hole injection capability is increased due to the deep molecular orbital level, and the driving voltage can be reduced, so that an organic electroluminescent element having excellent efficiency (light emission efficiency and power efficiency), life, luminance, driving voltage, and the like can be provided. Note that a CPL layer may be further stacked on the cathode layer of the organic electroluminescent element. In this way, when the CPL layer contains the compound represented by the above chemical formula (I), the light extraction effect is promoted due to the high optical refractive index, and thus, the luminance, lifetime, driving voltage, and the like of the organic electroluminescent element can be improved in particular.
The organic electroluminescent element of the present invention is not particularly limited in structure, and may have a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are sequentially stacked as a non-limiting example. A CPL layer may be further laminated on the cathode layer, as shown in fig. 1. In addition, the organic electroluminescent element of the present invention may have a structure in which an insulating layer or an adhesive layer is interposed between an electrode and an organic layer.
On the other hand, regarding the organic electroluminescent element of the present invention, in addition to one or more layers of the above organic layers containing the compound represented by the above chemical formula (I), the organic layers and the electrode may be formed using materials and methods known in the art.
Further, a substance which can be used as an anode included in the organic electroluminescent element according to the present invention is not particularly limited, and as non-limiting examples, metals such as vanadium, chromium, copper, zinc, gold, aluminum, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO-Al or SnO 2 A combination of a metal such as Sb and an oxide; polythiophenes, poly (3-methylthiophenes), poly [3, 4- (ethylene-1, 2-dioxy) thiophenes]Conductive polymers such as (PEDT), polypyrrole, and polyaniline; and carbon black and the like.
The substance usable as the cathode included in the organic electroluminescent element according to the present invention is not particularly limited, and as non-limiting examples, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multi-layer structure materials such as LiF/Al or LiO 2/Al.
The substance usable as the substrate included in the organic electroluminescent element according to the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, and the like can be used as non-limiting examples.
Preference is furthermore given to organic electroluminescent elements in which one or more layers are produced from solution, for example by spin coating, or by means of any desired printing method, for example screen printing, flexographic printing, offset printing, photoinitiated thermal imaging, thermal transfer, ink-jet printing or nozzle printing. Soluble compounds, for example obtained by appropriate substitution. These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, hybrid methods are possible, in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapor deposition.
These methods are generally known to those skilled in the art, and they can be applied to an organic electroluminescent element comprising the compound according to the present invention without inventive labor.
The invention therefore also relates to a method for producing an organic electroluminescent element according to the invention, at least one layer being applied by means of a sublimation method and/or at least one layer being applied by means of an organic vapor deposition method or by means of carrier gas sublimation and/or at least one layer being applied from solution by spin coating or by means of a printing method.
Furthermore, the invention relates to a pharmaceutical composition comprising at least one of said compounds of formula (I). The same preferences as indicated above for the organic electroluminescent elements apply to the compounds according to the invention. In particular, the compounds may furthermore preferably comprise further compounds. The treatment of the compounds of the formula (I) from the liquid phase, for example by spin coating or by printing methods, requires the treatment of formulations of the compounds of the formula (I). These formulations may be, for example, solutions, dispersions or emulsions. For this purpose, it may be preferred to use a mixture of two or more solvents. Suitable and preferred solvents are, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) -fenchytone, 1,2, 3, 5-tetramethylbenzene, 1,2, 4, 5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3, 4-dimethylanisole, 3, 5-dimethylanisole, acetophenone, alpha-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, 1-methylpyrrolidone, p-cymene, phenetole, 1, 4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1, 1-bis (3, 4-dimethylphenyl) ethane, or a mixture of these solvents.
The invention also provides an organic solar cell, which comprises a cathode, an anode and at least one organic layer arranged between the cathode and the anode, wherein at least one layer of the organic layer comprises the trimeric heterocyclic derivative.
Preferably, the electron acceptor material of the organic solar cell comprises the trimeric heterocyclic derivative.
A consumer product comprising an organic electroluminescent element according to the present invention, or comprising an organic solar cell according to the present invention.
Compared with the prior art, the invention has the beneficial effects that:
(1) the trimeric heterocyclic derivative has higher efficiency when used in an organic electroluminescent element and leads to a steep current-voltage curve under the conditions of use and low operating voltage, has high thermal stability and redox property, and has positive effects on the treatment of the trimeric heterocyclic derivative and on the storage stability of a solution.
(2) The trimeric heterocyclic derivative has high photoelectric conversion efficiency, high short-circuit current and open-circuit voltage and longer service life when being used in an organic solar cell.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a schematic view of an organic electroluminescent element of the present invention;
fig. 2 is a schematic view of an organic solar cell of the present invention.
Reference numerals
In FIG. 1: 101-substrate, 102-anode layer, 103-hole injection layer, 104-hole transport layer, 105-electron blocking layer, 106-light emitting layer, 107-electron transport layer, 108-electron injection layer, 109-cathode layer, 110-capping layer.
In fig. 2: 201-substrate, 202-anode layer, 203-hole injection layer, 204-active layer, 205-electron injection layer, 206-cathode layer.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the examples given herein without any inventive step, are within the scope of the present invention.
In the description of the present invention, "a plurality" means two or more unless otherwise specified; the terms "upper", "lower", and the like, indicate orientations or positional relationships that are based on the orientations or positional relationships shown in the drawings, are merely for convenience in describing the present invention and to simplify the description, and do not indicate or imply that the referenced devices or elements must have a particular orientation, be constructed and operated in a particular orientation, and thus, are not to be construed as limiting the present invention.
In the present invention, the preparation methods are all conventional methods unless otherwise specified. The starting materials used are, unless otherwise specified, available from published commercial sources and the percentages are, unless otherwise specified, percentages by mass.
Example 1
Preparation of Compound P-3:
under the protection of nitrogen, 40.0mmol of anhydrous ferric trichloride, 20.0mmol of 2, 5-bis (trifluoromethyl) furan and 150mL of nitromethane are heated to reflux and stirred for reaction for 12 hours, cooled to room temperature, decompressed, concentrated and dried, and separated and purified by a silica gel column to obtain a compound P-3 with the yield of 52 percent. MS (MALDI-TOF): m/z 606.9572[ M + H ]] + 。
Example 2
Preparation of Compound P-6:
under the protection of nitrogen, 40.0mmol of anhydrous ferric trichloride, 20.0mmol of 2, 5-difluorothiophene and 150mL of dichloromethane are added dropwise, 1 drop of concentrated sulfuric acid is added dropwise, the temperature is raised to reflux and stirring for reaction for 12 hours, the reaction is cooled to room temperature, the reaction product is concentrated under reduced pressure and dried, and the compound P-6 is obtained by silica gel column separation and purification, and the yield is 48%. MS (MALDI-TOF): m/z 354.9082[ M + H ]] + 。
Example 3
Preparation of Compound P-54:
0.25mL of concentrated sulfuric acid and 50mL of dry dichloromethane are mixed, the temperature is reduced to below 5 ℃ under the protection of nitrogen, 117.3mmol of anhydrous ferric trichloride is added in batches, the mixture is stirred for 30 minutes, 36.0mmol of 2, 5-bis (trifluorophenyl) thiophene is added dropwise, the mixture is stirred and reacts for 2 hours, and the volume is increasedStirring to room temperature for reaction for 12 hours, dropwise adding 50mL of methanol, filtering, washing a filter cake with methanol and water to obtain a compound P-54 which is a yellow solid and has the yield of 64%. MS (MALDI-TOF): m/z 1026.9832[ M + H ]] + 。 1 HNMR(δ、CDCl 3 )：7.42～7.37(12H，m)。
Example 4
Preparation of Compound P-68:
under the protection of nitrogen, 117.3mmol of anhydrous ferric trichloride and 50mL of dry dichloromethane are mixed, 36.0mmol of 3, 3' - ((1, 1-dimethyl silol-2, 5-diyl) dipyridine is added, the mixture is heated, refluxed, stirred and reacted for 48 hours, the temperature is reduced to room temperature, reaction liquid is poured into 250mL of ice water, an organic phase is separated, an aqueous phase is extracted by dichloromethane, the organic phase is dried, filtered, filtrate is concentrated under reduced pressure to be dry, and is separated and purified by a silica gel column to obtain a compound P-68, a yellow solid, the yield is 43 percent] + 。 1 HNMR(δ、CDCl 3 )：8.46(6H，s)；8.37～8.35(6H，m)；7.69～7.66(6H，m)；7.26～7.22(6H，m)；0.13(18H，s)。
The compounds shown in table 1 were prepared by a similar synthesis method to that of example 1 to example 4 described above.
TABLE 1 correspondence of reactants and products of synthesis and yields
Example 5
The preparation of compound P-119, comprising the steps of:
the first step is as follows: preparation of Compound Int-1
Under the protection of nitrogen, 130.0mmol of 2, 3-dibromo-1, 4-dimethoxynaphthalene (reactant 1) and 273.0mmol of phenylacetylene (reactant 2) were dissolved in 80mL of THF and 80mL of diisopropylethylamine, and 13.0mmol of cuprous iodide and 6.5mmol of PdCl were added 2 (PPh 3 ) 2 Heating, refluxing and stirring for reaction for 12 hours, cooling to room temperature, concentrating under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain a compound Int-1 with the yield of 85%.
The second step: preparation of Compound Iht-2
Dissolving 20.0mmol of Int-1 in 100mL of dichloromethane, adding 24.0mmol of N-methylpyrrolidone tribromide, stirring for reaction for 2 hours, adding 20mL of saturated sodium thiosulfate aqueous solution, separating out an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain the compound Int-2 with the yield of 89%.
The third step: preparation of Compound P-119
In the presence of nitrogen gasWhile keeping, 20.0mmol of Int-2, 20.0mmol of 2, 5-biphenylthiophene (reactant 3), 40.0mmol of anhydrous potassium carbonate, 2.0mmol of palladium acetate, and 4.0mmol of tricyclohexylphosphonium tetrafluoroborate dissolved in 80mL of NMP, heating to 120 ℃ and stirring for reaction for 12 hours, cooling to room temperature, pouring the reaction solution into 200mL of ice water, filtering, washing the filter cake with water and ethanol, and separating and purifying with a silica gel column to obtain the compound P-119 with a yield of 82%, MS (MALDI-TOF): m/z 745.2139[ M + H ]] + 。 1 HNMR(δ、CDCl 3 )：8.42～8.38(2H，m)；8.01～7.98(4H，m)；7.79～7.68(10H，m)；7.59～7.56(4H，m)；7.51～7.46(8H，m)；7.41～7.36(2H，m)；7.32～7.28(2H，m)。
The compounds shown in table 2 were prepared by a similar synthetic method with reference to example 5 above.
TABLE 2 correspondence table of reactants and synthesis products
Example 6
Preparation of Compound P-229:
30.0mmol of P-5 was dissolved in 120mL of chloroform, the temperature was lowered to 0 ℃ and 0.3mmol of m-chloroperoxybenzoic acid was added in portions, the mixture was warmed to room temperature, stirred and reacted for 12 hours, filtered, the filtrate was concentrated under reduced pressure and dried, and the product was separated and purified by a silica gel column to obtain Compound P229, a white solid, yield 72%, MS (MALDI-TOF): m/z 492.9127[ M + H] + 。
The compounds shown in table 3 were prepared by referring to the analogous synthetic methods described above.
TABLE 3 correspondence of reactants with synthesis products and yields
| Reactants | Product of | Yield of |
| P-6 | P-230 | 68％ |
| P-7 | P-231 | 84％ |
| P-8 | P-232 | 86％ |
| P-25 | P-233 | 75％ |
| P-26 | P-234 | 78％ |
| P-81 | P-235 | 88％ |
| P-82 | P-236 | 57％ |
The OLED element provided by the invention is shown in FIG. 1, and the OLED element provided by the invention is prepared by taking the OLED element structure shown in FIG. 1 as an example. In fig. 1, 101 denotes a substrate, 102 denotes an anode layer, 103 denotes a hole injection layer, 104 denotes a hole transport layer, 105 denotes an electron blocking layer, 106 denotes a light emitting layer, 107 denotes an electron transport layer, 108 denotes an electron injection layer, 109 denotes a cathode layer, and 110 denotes a CPL layer.
Comparative example 1
An organic electroluminescent element was prepared using the following compound formula C as a doping material for the hole injection layer, formula E as a material for the hole injection layer host, formula D as a material for the hole transport layer, formula H as a material for the electron blocking layer, formula a as a material for the host of the light emitting layer, formula B as a doping material for the light emitting layer, formula G as a doping material for the electron transport layer, LiQ as a material for the host of the electron transport layer, formula F as a material for the CPL layer.
Will be provided with
The organic electroluminescent element of comparative example 1 was prepared by depositing an EL evaporator manufactured by DOV corporation on ITO glass in this order.
Example 7
An organic electroluminescent element was produced in the same manner as in comparative example 1 except that the compound C was replaced with the compounds P-1 to P-92 and P-229 to P-236 of the present invention:
the driving voltage and current efficiency of the organic electroluminescent elements prepared in example 7 and comparative example 1 and the lifetime of the elements were measured using a digital source meter and a luminance meter. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent element reached 1000cd/m 2 The current density is measured at the same time as the driving voltage; the ratio of the brightness to the current density is the current efficiency; the LT 90% lifetime test is as follows: using a luminance meter at 1000cd/m 2 At luminance, the luminance of the organic electroluminescent element was measured by maintaining a constant currentDegree attenuation of 900cd/m 2 Time in hours. All results are summarized in table 4, and all results are reported as relative values normalized to the results of comparative example 1.
TABLE 4 test results of the performance of each element
As shown in the table, the trimeric heterocyclic compound provided by the invention is used as a hole injection layer material to prepare an OLED element which has low driving voltage and high efficiency, and the LT 90% service life of the element is greatly prolonged under the condition that the initial luminous brightness of the element is 1000 nits.
Example 8
An organic electroluminescent element was produced in the same manner as in comparative example 1 except that the compound G was replaced with the compounds P-1 to P-236 of the present invention:
all results are summarized in table 5 with reference to the test method of example 7, and are reported as relative values normalized to the results of comparative example 1.
TABLE 5 test results of the properties of the respective elements
As can be seen from the above table, the trimeric heterocyclic compound of the invention is used as an electron transport layer material to prepare each OLED element which has low driving voltage and high efficiency, and under the condition that the initial luminous brightness of the element is 1000 nits, the LT 90% service life of the element is greatly improved.
The above description is only for the specific embodiments of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily conceive of the changes or substitutions within the technical scope of the present invention, and all the changes or substitutions should be covered within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the appended claims.
Claims (10)
1. A trimeric heterocyclic derivative, wherein the structural formula of the trimeric heterocyclic derivative is shown as formula (I):
wherein, X 1 、X 2 、X 3 Each independently selected from O, S, SO 2 、SiR 7 R 8 、BR 7 、NR 8 、PR 7 Or POR 8 ；
R 1 、R 2 、R 3 、R 4 、R 5 、R 6 Each independently selected from the group consisting of fluorine, nitrile, having C 1 ～C 40 Straight chain alkyl of (2) having C 3 ～C 40 A branched or cyclic alkyl group of (2), having C 1 ～C 40 Linear heteroalkyl group of (C) 3 ～C 40 A branched or cyclic heteroalkyl group of (2), substituted or unsubstituted C 6 ～C 60 Arylboron group of (A), substituted or unsubstituted C 6 ～C 60 Aryl of (A), substituted or unsubstituted C 6 ～C 60 Aryl silicon group, substituted or unsubstituted C 2 ～C 60 Of (a) heteroaryl, R 1 And R 2 、R 3 And R 4 Or R 5 And R 6 May be optionally joined or fused to form a substituted or unsubstituted ring, and R 1 、R 2 、R 3 、R 4 、R 5 、R 6 Optionally substituted with fluorine atoms or nitrile groups;
R 7 、R 8 each independently selected from the group consisting of 1 ～C 40 Straight chain alkyl of (2) having C 3 ～C 40 A branched or cyclic alkyl group having C 6 ～C 60 Or have C 2 ～C 60 And R is 7 、R 8 Optionally substituted with fluorine atoms or nitrile groups.
2. The trimeric heterocyclic derivative according to claim 1, wherein the trimeric heterocyclic derivative is selected from the group consisting of the structures represented by formulae (1) to (62):
3. trimeric heterocyclic derivative according to any of the claims 1 or 2, characterized in, that C 2 ～C 60 Is selected from the group consisting of structures represented by formulas (63) to (81):
said C is 6 ～C 60 The aryl group of (a) is a group consisting of the structures represented by formulae (82) to (100):
wherein the dashed bond indicates the position at which the substituent is attached;
T 1 selected from O, S, NR or Si (R) 2 ；
R is selected, identically or differently on each occurrence, from the group consisting of hydrogen atom, deuterium atom, fluorine, chlorine, nitrile group, nitro group, trifluoromethyl group, trifluoroethyl group, trifluoromethoxy group, pentafluoroethyl group, pentafluoroethoxy group, trifluoroacetyl group, trifluoromethylthio group, pentafluorothio group, compounds having C 1 ～C 40 Straight chain alkyl of (2) having C 3 ～C 40 A branched or cyclic alkyl group having C 6 -C 60 Or have C 2 -C 60 Heteroaryl group of (a).
4. A tricyclic heterocyclic derivative according to any one of claims 1 to 3, wherein R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 Each independently selected from the group consisting of fluorine, chlorine, nitrile, trifluoromethyl, trifluoroethyl, trifluoromethoxy, pentafluoroethyl, pentafluoroethoxy, trifluoroacetyl, trifluoromethylthio, pentafluorophenylthio, pyridyl, pyrimidinyl, triazinyl, 2, 6-dimethyl-1, 3, 5-triazinyl, 2, 6-bis (trifluoromethyl) -1, 3, 5-triazinyl, fluorophenyl, difluorophenyl, trifluorophenyl, tetrafluorophenyl, pentafluorophenyl, cyanophenyl, nitrilodiphenyl, nitrilotrifluorophenyl, trifluoromethoxyphenyl, trifluoromethoxyfluorophenyl, trifluoromethoxydifluorophenyl, trifluoromethoxytrifluorophenyl, trifluoromethoxytetrafluorophenyl, trifluoromethylfluorophenyl, trifluoromethyldifluorophenyl, trifluoromethyltrifluorophenyl, trifluoromethyltetrafluorophenyl, trifluoromethyltetrafluorophenylt, trifluoromethyltetrafluorophenyl, trifluoromethyltetraflurylphenyl, trifluoromethyltetrafluryltetrafluridiphenyl, and, Pentafluoroethylphenyl, pentafluoroethoxyphenyl, nitrophenyl, methylsulfonylphenyl, trifluoromethylsulfonylphenyl, trifluoromethylthiophenyl, pentafluorothiophenyl, fluoropyridyl, difluoropyridinyl, trifluoropyridyl, tetrafluoropyridinyl, R 1 And R 2 、R 3 And R 4 Or R 5 And R 6 May be optionally joined or fused to form a substituted or unsubstituted ring;
R 7 、R 8 each independently selected from the group consisting of methyl, nitrile, trifluoromethyl, trifluoroethyl, pentafluoroethyl, acetonitrile, difluoroacetonitrile, pyridyl, pyrimidyl, triazinyl, 2, 6-dimethyl-1, 3, 5-triazinyl, 2, 6-bis (trifluoromethyl) -1, 3, 5-triazinyl, fluorophenyl, difluorophenyl, trifluorophenyl, tetrafluorophenyl, pentafluorophenyl, cyanophenyl, nitrilodiphenyl, nitrilotrifluorophenyl, trifluoromethoxyphenyl, trifluoromethoxyfluorophenyl, trifluoromethoxydifluorophenyl, trifluoromethoxytrifluorophenyl, trifluoromethoxytetrafluorotetrafluorophenyl, trifluoromethylphenyl, trifluoromethylfluorophenyl, trifluoromethyldifluorophenyl, trifluoromethyltrifluorophenyl, trifluoromethyltetrafluorophenyl, pentafluoroethylphenyl, pentafluoroethyl, thioethyl, thio,Pentafluoroethoxyphenyl group, nitrophenyl group, methylsulfonylphenyl group, trifluoromethylsulfonylphenyl group, trifluoromethylthiophenyl group, pentafluorothiophenyl group, fluoropyridyl group, difluoropyridinyl group, trifluoropyridinyl group, tetrafluoropyridinyl group.
5. The trimeric heterocyclic derivative according to any of the claims 3 or 4, characterized in that R is selected from the group consisting of hydrogen, fluoro, chloro, nitrile, nitro, trifluoromethyl, trifluoroethyl, trifluoromethoxy, pentafluoroethyl, pentafluoroethoxy, trifluoroacetyl, trifluoromethylthio, pentafluorothio.
6. The trimeric heterocyclic derivative according to any of claims 1-5, characterized in that it is selected from the group consisting of the structures shown below:
7. use of the trimeric heterocyclic derivative of any of the claims 1-6 in the field of flexible transparent displays, transparent films, optical communication, organic thin film transistors or photovoltaics of solar cells.
8. An organic electroluminescent element comprising a first electrode, a second electrode, a CPL layer and at least one organic layer interposed between said first electrode and said second electrode, characterized in that at least one of said organic layers or CPL layer comprises the trimeric heterocyclic derivative of any one of claims 1 to 6;
preferably, the electron transport layer or the hole injection layer of the organic electroluminescent element comprises the trimeric heterocyclic derivative of any one of claims 1 to 6.
9. An organic solar cell comprising a cathode, an anode and at least one organic layer disposed between the cathode and the anode, wherein at least one of the organic layers comprises the trimeric heterocyclic derivative of any one of claims 1-6;
preferably, the electron acceptor material of the organic solar cell comprises the trimeric heterocyclic derivative of any one of claims 1-6.
10. A consumer product comprising the organic electroluminescent element of claim 8, or comprising the organic solar cell of claim 9.
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