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CN120569385A - Heterocyclic compounds for organic electroluminescent devices - Google Patents

Heterocyclic compounds for organic electroluminescent devices

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Publication number
CN120569385A
CN120569385A CN202480007967.4A CN202480007967A CN120569385A CN 120569385 A CN120569385 A CN 120569385A CN 202480007967 A CN202480007967 A CN 202480007967A CN 120569385 A CN120569385 A CN 120569385A
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菲利普·施特塞尔
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Merck Patent GmbH
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Merck Patent GmbH
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    • 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
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    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
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    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
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    • 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
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    • 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
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Abstract

本发明涉及适合用于电子器件中的杂环化合物，并且涉及含有这些杂环化合物的电子器件、特别是有机电致发光器件。The present invention relates to heterocyclic compounds suitable for use in electronic devices, and to electronic devices, in particular organic electroluminescent devices, containing these heterocyclic compounds.

Description

Heterocyclic compounds for organic electroluminescent devices
The present invention relates to heterocyclic compounds for use in electronic devices, in particular in organic electroluminescent devices, and to electronic devices, in particular organic electroluminescent devices, comprising these materials.
Electronic devices containing organic compounds are well known and commercially available. These devices may comprise, for example, in each case one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers and/or charge production layers. In general, there is a need for improvements in the performance of these devices, particularly the compounds used in the layers detailed above have a significant impact on the performance of the device.
In addition, the luminescent materials used in organic electroluminescent devices are typically phosphorescent organometallic complexes. For quantum mechanical reasons, up to four times the energy and power efficiency can be achieved using organometallic compounds as phosphorescent emitters. In electroluminescent devices, in particular also electroluminescent devices exhibiting triplet emission (phosphorescence), improvements are generally still needed. The properties of phosphorescent electroluminescent devices depend not only on the triplet emitters used. More particularly, other materials such as matrix materials are also particularly important herein. Thus, improvements in these materials can also lead to significant improvements in the performance of electroluminescent devices.
Similar remarks apply to organic electroluminescent devices based on fluorescent emitters or emitters exhibiting TADF (thermally activated delayed fluorescence).
JP 2021-166280A and CN 112300144A disclose heterocyclic compounds which can be used in organic electroluminescent devices. The compounds according to the invention are not disclosed.
In general, in the case of these materials, for example, as host materials and hole-transporting materials and/or electron-transporting materials, improvements are still needed, in particular in terms of efficiency and operating voltage of the device, as well as in terms of lifetime.
It is therefore an object of the present invention to provide a compound which is suitable for use in organic electronic devices, in particular organic electroluminescent devices, and which gives rise to good device performance when used in such devices, and to corresponding electronic devices.
More particularly, it is an object addressed by the present invention to provide compounds that lead to high lifetime, good efficiency and low operating voltages. In particular, the properties of the matrix material also have a significant influence on the lifetime and efficiency of the organic electroluminescent device.
It may be seen as a further object of the present invention to provide compounds suitable for use in phosphorescent or fluorescent electroluminescent devices, in particular as matrix materials. It is a particular object of the present invention to provide matrix materials suitable for blue, green, yellow and red phosphorescent electroluminescent devices, in particular for blue phosphorescent electroluminescent devices.
Furthermore, the compounds, especially when they are used as host materials, as hole transport materials or as electron transport materials in organic electroluminescent devices, should lead to devices with excellent lifetime and efficiency.
Another object may be considered to provide an electronic device with excellent properties that is very inexpensive and stable in quality.
Furthermore, it should be possible to use or retrofit electronic devices for a number of purposes. More particularly, the performance of the electronic device should be maintained over a wide temperature range.
It has surprisingly been found that this object is achieved by specific compounds which are described in detail later, which are very suitable for use in electroluminescent devices and which cause organic electroluminescent devices to exhibit good properties, in particular in terms of lifetime, color purity and efficiency, and operating voltage. The present invention therefore provides these compounds and electronic devices, in particular organic electroluminescent devices, comprising these compounds.
The present invention provides a compound comprising at least one structure of formula (I), preferably a compound of formula (I),
Wherein the symbols are as follows:
z is identical or different on each occurrence and is Ar or R, preferably Ar;
W 1 is identical or different on each occurrence and is-C (R a)2-(Y)n-C(Rb)2 -group, is-C (R c)＝C(Rc) -group or is an ortho-linked aromatic or heteroaromatic ring system which has from 5 to 60 aromatic ring atoms and can be substituted by one or more R d groups;
W 2 is identical or different on each occurrence and is-C (R a)2-(Y)n-C(Rb)2 -group, is-C (R c)＝C(Rc) -group or is an ortho-linked aromatic or heteroaromatic ring system which has from 5 to 60 aromatic ring atoms and can be substituted by one or more R d groups;
R is identical or different on each occurrence and is a straight-chain alkyl, alkoxy or thioalkoxy radical of from 1 to 40 carbon atoms or an alkenyl or alkynyl radical of from 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy radical of from 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl radicals can in each case be substituted by one or more R e radicals, where one or more non-adjacent CH 2 radicals can be replaced by ReC＝CRe、C≡C、Si(Re)2、C＝O、C＝S、C＝Se、C＝NRe、-C(＝O)O-、-C(＝O)NRe-、NRe、P(＝O)(Re)、-O-、-S-、SO or SO 2, or an aromatic or heteroaromatic ring system of from 5 to 60 aromatic ring atoms and in each case can be substituted by one or more R e radicals, or an aralkyl or heteroaralkyl radical of from 5 to 60 aromatic ring atoms and of from 1 to 10 carbon atoms in the alkyl radical and can be substituted by one or more R e radicals;
ar is identical or different on each occurrence and is an aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms and which may be substituted by one or more R e groups, while two Ar groups bonded to the same carbon, silicon, nitrogen, phosphorus or boron atom may also be bridged together by a single bond or a bridging group selected from B(Re)、C(Re)2、Si(Re)2、C＝O、C＝NRe、C＝C(Re)2、O、S、S＝O、SO2、N(Re)、P(Re) and P (=O) R e;
r a、Rb is identical or different on each occurrence and is a linear alkyl, alkoxy or thioalkoxy radical of OH,F,Cl,Br,I,CN,NO2,N(Ar')2,N(R1)2,C(＝O)N(Ar')2,C(＝O)N(R1)2,C(Ar')3,C(R1)3,Si(Ar')3,Si(R1)3,B(Ar')2,B(R1)2,C(＝O)Ar',C(＝O)R1,P(＝O)(Ar')2,P(＝O)(R1)2,P(Ar')2,P(R1)2,S(＝O)Ar',S(＝O)R1,S(＝O)2Ar',S(＝O)2R1,OSO2Ar',OSO2R1, having 1 to 40 carbon atoms or an alkenyl or alkynyl radical of 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy radical of 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl radicals can in each case be substituted by one or more R 1 radicals, where one or more non-adjacent CH 2 radicals can be replaced by R1C＝CR1、C≡C、Si(R1)2、C＝O、C＝S、C＝Se、C＝NR1、-C(＝O)O-、-C(＝O)NR1-、NR1、P(＝O)(R1)、-O-、-S-、SO or SO 2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and in each case can be substituted by one or more R 1 radicals, or an aryloxy or heteroaryloxy radical having 5 to 60 aromatic ring atoms and which can be substituted by one or more R 1 radicals;
n is 0 or 1, wherein when n=0, the Y group is absent and the two-C (R a)2 -and-C (R b)2 -groups are directly bonded to each other;
y is identical or different on each occurrence and is C (R c)2、C(Rc)2-C(Rc)2、C(Rc)＝C(Rc);
R c、Rd、Re is identical or different on each occurrence and is a straight-chain alkyl, alkoxy or thioalkoxy radical of H,D,OH,F,Cl,Br,I,CN,NO2,N(Ar')2,N(R1)2,C(＝O)N(Ar')2,C(＝O)N(R1)2,C(Ar')3,C(R1)3,Si(Ar')3,Si(R1)3,Ge(Ar')3,Ge(R1)3,B(Ar')2,B(R1)2,C(＝O)Ar',C(＝O)R1,P(＝O)(Ar')2,P(＝O)(R1)2,P(Ar')2,P(R1)2,S(＝O)Ar',S(＝O)R1,S(＝O)2Ar',S(＝O)2R1,OSO2Ar',OSO2R1, having 1 to 40 carbon atoms or an alkenyl or alkynyl radical of 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy radical of 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl radicals can in each case be substituted by one or more R 1 radicals, where one or more non-adjacent CH 2 radicals can be replaced by R1C＝CR1、C≡C、Si(R1)2、Ge(R1)2、C＝O、C＝S、C＝Se、C＝NR1、-C(＝O)O-、-C(＝O)NR1-、NR1、P(＝O)(R1)、-O-、-S-、SO or SO 2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and in each case can be substituted by one or more R 1 radicals, or an aryloxy or heteroaryloxy radical having 5 to 60 aromatic ring atoms and which can be substituted by one or more R 1 radicals, where simultaneously two R c、Rd、Re radicals can also form a ring system with one another or with other radicals, preferably with R a;
Ar 'is identical or different on each occurrence and is an aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms and which may be substituted by one or more R 1 groups, where two Ar' groups bonded to the same carbon, silicon, nitrogen, phosphorus or boron atom may also be bridged to each other by a single bond or a bridging group selected from B(R1)、C(R1)2、Si(R1)2、C＝O、C＝NR1、C＝C(R1)2、O、S、S＝O、SO2、N(R1)、P(R1) and P (=O) R 1;
R 1 is identical or different on each occurrence and is H,D,F,Cl,Br,I,CN,NO2,N(Ar")2,N(R2)2,C(＝O)Ar",C(＝O)R2,P(＝O)(Ar")2,P(Ar")2,B(Ar")2,B(R2)2,C(Ar")3,C(R2)3,Si(Ar")3,Si(R2)3,Ge(Ar")3,Ge(R2)3, a straight-chain alkyl, alkoxy or thioalkoxy radical having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy radical having 3 to 40 carbon atoms or an alkenyl radical having 2 to 40 carbon atoms, which radicals may each be substituted by one or more R 2 radicals, where one or more non-adjacent CH 2 radicals may be replaced by -R2C＝CR2-、-C≡C-、Si(R2)2、Ge(R2)2、C＝O、C＝S、C＝Se、C＝NR2、-C(＝O)O-、-C(＝O)NR2-、NR2、P(＝O)(R2)、-O-、-S-、SO or SO 2 and where one or more hydrogen atoms may be replaced by D, F, cl, br, I, CN or NO 2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and which may in each case be substituted by one or more R 2 radicals, or an aryloxy or heteroaryloxy radical having 5 to 60 aromatic ring atoms and which may be substituted by one or more R 2 radicals, or an aralkyl or heteroarylalkyl radical having 5 to 60 aromatic ring atoms and which may be substituted by one or more R 2 radicals, or a combination of these radicals, two or more R23 and one or more R5698 radicals may form part of a ring system which may be adjacent to one another;
Ar 'is identical or different on each occurrence and is an aromatic or heteroaromatic ring system having from 5 to 30 aromatic ring atoms and which may be substituted by one or more R 2 groups, where the two Ar' groups bound to the same carbon, silicon, nitrogen, phosphorus or boron atom may also be bridged to each other by a single bond or a bridging group selected from B(R2)、C(R2)2、Si(R2)2、C＝O、C＝NR2、C＝C(R2)2、O、S、S＝O、SO2、N(R2)、P(R2) and P (=O) R 2;
R 2 is identical or different on each occurrence and is selected from H, D, F, CN, an aliphatic hydrocarbon radical having from 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system having from 5 to 30 aromatic ring atoms in which one or more hydrogen atoms can be replaced by D, F, cl, br, I or CN, and which can be substituted by one or more alkyl radicals each having from 1 to 4 carbon atoms, two or more, preferably adjacent substituents R 2 together forming a ring system;
Characterized in that at least one of the W 1、W2 groups is a-C (R a)2-(Y)n-C(Rb)2 -group).
It is preferably possible that the R groups are identical or different on each occurrence and are selected from the group consisting of straight-chain alkyl, alkoxy or thioalkoxy groups of H,D,C(Ar)3,C(Re)3,Si(Ar)3,Si(Re)3,B(Ar)2,B(Re)2,C(＝O)Ar,C(＝O)Re,P(＝O)(Ar)2,P(＝O)(Re)2,P(Ar)2,P(Re)2,S(＝O)Ar,S(＝O)Re,S(＝O)2Ar,S(＝O)2Re,OSO2Ar,OSO2Re, having 1 to 40 carbon atoms or alkenyl or alkynyl groups of 2 to 40 carbon atoms or branched or cyclic alkyl, alkoxy or thioalkoxy groups of 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl groups can in each case be substituted by one or more R e groups, where one or more non-adjacent CH 2 groups can be replaced by ReC＝CRe、C≡C、Si(Re)2、C＝O、C＝S、C＝Se、C＝NRe、-C(＝O)O-、-C(＝O)NRe-、NRe、P(＝O)(Re)、-O-、-S-、SO or SO 2, or aromatic or heteroaromatic ring systems of 5 to 60 aromatic ring atoms and in each case can be substituted by one or more R e groups, or aralkyl or heteroaralkyl groups of 5 to 60 aromatic ring atoms and of 1 to 10 carbon atoms in the alkyl groups and can be substituted by one or more R e groups, while one R group can form with the other groups, preferably with R a. Compounds wherein R is selected from H、D、OH、F、Cl、Br、I、CN、NO2、N(Ar)2、N(Re)2、C(＝O)N(Ar)2、C(＝O)N(Re)2 are particularly suitable as intermediates for the preparation of preferred compounds of the invention.
Aryl groups in the context of the present invention contain from 6 to 40 carbon atoms, heteroaryl groups in the context of the present invention contain from 3 to 40 carbon atoms and at least one heteroatom, provided that the sum of carbon atoms and heteroatoms is at least 5. The heteroatom is preferably selected from N, O and/or S. Aryl or heteroaryl groups are understood here to mean simple aromatic rings, i.e. benzene, or simple heteroaromatic rings, such as pyridine, pyrimidine, thiophene, etc., or fused (ring-extended) aryl or heteroaryl groups, such as naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc. In contrast, aromatic compounds such as biphenyls, which are linked to each other by single bonds, are not referred to as aryl or heteroaryl groups, but are referred to as aromatic ring systems.
Electron-deficient heteroaryl groups in the context of the present invention are heteroaryl groups having at least one heteroaromatic six-membered ring with at least one nitrogen atom. Other aromatic or heteroaromatic five-membered rings or six-membered rings may be fused to the six-membered ring. Examples of electron-deficient heteroaryl groups are pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinazoline or quinoxaline.
In the context of the present invention, aromatic ring systems contain from 6 to 60 carbon atoms in the ring system. In the context of the present invention, heteroaromatic ring systems contain 3 to 60 carbon atoms and at least one heteroatom in the ring system, provided that the sum of carbon atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O and/or S. In the context of the present invention, an aromatic or heteroaromatic ring system is understood to mean a system which does not have to contain only aryl or heteroaryl groups, but in which two or more aryl or heteroaryl groups can also be linked by non-aromatic units, for example carbon, nitrogen or oxygen atoms. For example, in the context of the present invention, systems such as fluorene, 9' -spirobifluorene, 9-diaryl fluorene, triarylamine, diaryl ether, stilbene, etc. should also be regarded as aromatic ring systems, and so should systems in which two or more aryl groups are linked, for example by short alkyl groups. Preferably, the aromatic ring system is selected from fluorene, 9' -spirobifluorene, 9-diarylamine or groups in which two or more aryl and/or heteroaryl groups are linked to each other by single bonds.
In the context of the present invention, an aliphatic hydrocarbon radical or alkyl radical or alkenyl or alkynyl radical which may contain from 1 to 20 carbon atoms and in which the individual hydrogen atoms or CH 2 groups may also be replaced by the abovementioned radicals is preferably understood to be a 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, trifluoromethyl, pentafluoroethyl, 2-trifluoroethyl, vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl radical. Alkoxy having 1 to 40 carbon atoms is preferably understood to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptoxy, n-octoxy, cyclooctyloxy, 2-ethylhexoxy, pentafluoroethoxy and 2, 2-trifluoroethoxy. Thioalkyl having from 1 to 40 carbon atoms is to be understood as meaning, in particular, methylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, n-pentylthio, zhong Wuliu-yl, n-hexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, 2-trifluoroethylthio, vinylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, heptenylthio, cycloheptenylthio, octenylthio, cyclooctenylthio, ethynylthio, propynylthio, butynylthio, pentynylthio, hexynylthio, heptynylthio or Xin Guiliu-yl. In general, the alkyl, alkoxy or thioalkyl groups according to the invention may be straight-chain, branched or cyclic, in which one or more non-adjacent CH 2 groups may be replaced by the abovementioned groups, and furthermore one or more hydrogen atoms may also be replaced by D, F, cl, br, I, CN or NO 2, preferably F, cl or CN, more preferably F or CN, particularly preferably CN.
Aromatic or heteroaromatic ring systems which have from 5 to 60 or from 5 to 40 aromatic ring atoms and which in each case can also be substituted by the abovementioned groups and which can be linked to the aromatic or heteroaromatic system via any desired position are understood to mean, in particular, radicals derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chicory, perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, diphenylene, terphenyl, ditrimene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis-or trans-indenofluorene, cis-or trans-indenocarbazole, cis-or trans-indolocarbazole, trimeric indene, spiroindene, spiroisothriminane, furan, benzofuran, isobenzofuran, dibenzofuran, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5, 6-quinoline, benzo-6, benzo-quinoline, 7-7, 7-benzo-7, 8-thiazine, phenothiazineOxazine, pyrazole, indazole, imidazole, benzimidazole, naphthazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxalinoimidazole,Azole and benzoAzole and naphthoAzole and anthraceneAzole, phenanthroAzole, isoOxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, hexaazatriphenylene, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1, 5-diazaanthracene, 2, 7-diazapyrene, 2, 3-diazapyrene, 1, 6-diazapyrene, 1, 8-diazapyrene, 4,5,9, 10-tetraazaperylene, pyrazine, phenazine, phenone, and the likeOxazine, phenothiazine, fluororuber, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2, 3-triazole, 1,2, 4-triazole, benzotriazole, 1,2, 3-holoDiazole, 1,2,4-Diazole, 1,2,5-Diazole, 1,3,4-Diazoles, 1,2, 3-thiadiazoles, 1,2, 4-thiadiazoles, 1,2, 5-thiadiazoles, 1,3, 4-thiadiazoles, 1,3, 5-triazines, 1,2, 4-triazines, 1,2, 3-triazines, tetrazoles, 1,2,4, 5-tetrazines, 1,2,3, 4-tetrazines, 1,2,3, 5-tetrazines, purines, pteridines, indolizines, and benzothiadiazoles, or groups derived from combinations of these systems.
In the context of the present specification, the expression that two or more groups together may form a ring is understood to mean in particular that the two groups are linked to each other by chemical bonds under conditions in which the two hydrogen atoms are formally eliminated. This is illustrated by the following scheme:
However, in addition, the above expression is also understood to mean that if one of the two groups is hydrogen, the second group is bonded to the position to which the hydrogen atom is bonded, thereby forming a ring. This will be illustrated by the following scheme:
In a preferred configuration, the compounds of the invention may preferably comprise at least one structure of the formulae (I-1) to (I-18), more preferably selected from the compounds of the formulae (I-1) to (I-18),
Wherein the symbols Z, R a、Rb and R c have the definitions given above, in particular for formula (I), V is B (R d)、C(Rd)2、Si(Rd)2、N(Rd), O, S, preferably C (R d)2、Si(Rd)2、N(Rd), O, and X is N or C (R d), preferably C (R d), wherein R d has the definition given above, in particular for formula (I).
Preference is given here to structures/compounds of the formulae (I-1) to (I-4), and particular preference is given to structures/compounds of the formulae (I-1) to (I-3), very particular preference to structures/compounds of the formula (I-1).
The Z group is preferably Ar, wherein the preferred configuration of Ar groups is also presented below in connection with Ar groups that may be part of the Z group.
It is preferably possible that the Ar or R groups are aromatic or heteroaromatic ring systems having from 5 to 18, preferably from 5 to 13, more preferably from 6 to 13, aromatic ring atoms and which may be substituted by one or more R e groups.
It is also possible that Ar groups are identical or different on each occurrence and are selected from phenyl, biphenyl, terphenyl, tetrabiphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or benzidine, which groups may each be substituted by one or more R e groups, preferably phenyl, biphenyl, fluorene, dibenzofuran, benzidine, carbazole, indolocarbazole.
The Ar group may preferably be a phenyl group substituted with at least one R e group, where the substituents are in the ortho, meta or para positions based on the binding site of the nitrogen atom. For example, if the R e group is a phenyl group, then an ortho-, meta-, or para-biphenyl group may be formed.
If the Ar group is a triazine group, it is preferably possible for the triazine group to have two R e groups which are not H or D, where two R e groups are preferably aromatic or heteroaromatic ring systems which have from 5 to 60, preferably from 6 to 30, aromatic ring atoms and which can in each case be substituted by one or more R 1 groups.
Furthermore, the Ar group may preferably be a phenyl group substituted with at least one R e group, wherein the substituents together with the phenyl group represented by the Ar group form a fluorene group which may be bonded via the 1-position, 2-position, 3-position or 4-position, a spirobifluorene group which may be bonded via the 1-position, 2-position, 3-position or 4-position, an indole group, a benzofuran group, a benzothiophene group, a carbazole group which may be bonded via the 1-position, 2-position, 3-position or 4-position, a dibenzofuran group which may be bonded via the 1-position, 2-position, 3-position or 4-position, a dibenzothiophene group which may be bonded via the 1-position, 2-position, 3-position or 4-position, an indenocarbazole group or an indolocarbazole group.
In another configuration, it is possible that the structures/compounds according to the invention comprise at least one electron-transporting group and/or electron-withdrawing group, preferably a triazine group and/or a phosphine oxide group. Electron transporting groups are well known in the art and facilitate the ability of a compound to transport and/or conduct electrons. Examples of electron-transporting groups are pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, quinoline, isoquinoline, imidazole and/or benzimidazole groups, particularly preferably triazine groups. The electron withdrawing group comprises in particular S (=o) 2Ar'、S(＝O)2Re、B(Re)、B(Ar')、P(Re) O, P (Ar') O, which may be present, for example, as a substituent of the Ar or R group. Furthermore, these electron withdrawing groups may also be present as substituents R a、Rb、Rc、Rd、Re in the structures/compounds of formula (I) and/or formulae (I-1) to (I-18), for example as substituents B(Ar')2、B(R1)2、P(＝O)(Ar')2、P(＝O)(R1)2、S(＝O)2Ar'、S(＝O)2R1 in the structures/compounds of formula (I) and/or formulae (I-1) to (I-18). Furthermore, the electron withdrawing group comprises, for example, a c=o group or a CN group, which may be present in the structure as substituents, for example as substituents C (=o) Ar, C (=o) Ar', C (=o) R e、C(＝O)Re or C (=o) R 1.
In another configuration, it is possible that the structure/compound according to the invention comprises at least one hole transporting group. Hole transporting groups are also known in the art, and they preferably comprise triarylamine or carbazole groups.
The compounds according to the invention are particularly suitable as host materials for light emitters, preferably for singlet, triplet and TADF emitters, in electronic devices, electron transport materials, electron injection materials, hole conduction materials, hole injection materials, electron blocking materials, hole blocking materials. The specific nature of the compounds described here depends on the type and number of the corresponding functional groups. Compounds containing one, two or more electron transporting groups and/or electron withdrawing groups but not containing hole transporting groups are particularly suitable as host materials, electron transporting materials, electron injecting materials and/or hole blocking materials. Compounds comprising one, two or more hole transporting groups but not comprising electron transporting groups and/or electron withdrawing groups are particularly suitable as host materials, hole conducting materials, hole injecting materials and/or electron blocking materials. Compounds comprising one, two or more hole transporting groups and one, two or more electron transporting and/or electron withdrawing groups are particularly suitable as host materials.
Other possibilities are that at least one of the R, R c、Rd、Re groups is not H, preferably not H, D, OH, NO 2, F, cl, br, I. Other possibilities are that none of the R, R a、Rb、Rc、Rd、Re groups are OH, NO 2, F, cl, br, I.
In another preferred embodiment, it is possible that the compounds of the invention comprise structures of the formulae (II-1) to (II-8), wherein the compounds of the invention can more preferably be selected from the compounds of the formulae (II-1) to (II-8),
Wherein the symbols R a、Rb、Rc and R d have the definitions given above, in particular for formula (I), and the other symbols are as follows:
Y e is identical or different in each case and is B(Re)、C(Re)2、Si(Re)2、Ge(Re)2、C＝O、C＝NRe、C＝C(Re)2、O、S、S＝O、SO2、N(Re)、P(Re) or P (=o) R e, preferably N (R e)、O、S、B(Re)、C(Re)2 or Si (R a)2, more preferably N (R e), O or S, wherein R e has the definition given above, in particular for formula (I), or if a group is bonded to the structure, Y e is B, C (R e)-、Si(Re) -;
X e is identical or different on each occurrence and is N, CR e, or X e is C if a group is bonded to the structure, X e is preferably CR e or C, provided that no more than three X e groups in the ring are N, wherein R e has the definition given above, in particular for formula (I);
m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2.
Here, the structures/compounds of the formulae (II-1), (II-2), (II-3), (II-5), (II-6) and (II-7) are preferred, and the structures/compounds of the formulae (II-1) and (II-5) are particularly preferred.
In the formulae (II-1) to (II-8), it is possible that X e is C if a group is bonded to a specific structure. This group is especially a ring structure having a Y e group, and is shown in formulas (II-5) to (II-8). The ring structure may be bonded here via an X e group or via Y e, the latter case Y e being B, C (R e)-、Si(Re) -.
In one embodiment, it is possible that in the structures/compounds of formulae (II-1) to (II-8) no more than three, preferably two, X e groups per ring are N, preferably all X e are CR e, preferably at least one, more preferably at least two, X e groups per ring are selected from C-H and C-D.
It is further possible that at least one, preferably at least two, more preferably three X e groups per ring are N, wherein these groups are preferably not adjacent. These structures/compounds preferably contain electron-transporting groups and are therefore particularly suitable as electron-transporting materials and/or matrix materials.
In another preferred embodiment, it is possible that the compounds of the invention comprise structures of the formulae (III-1) to (III-32), wherein the compounds of the invention can more preferably be selected from the compounds of the formulae (III-1) to (III-32),
Wherein the symbols R a、Rb、Rc、Rd and R e have the definitions given above, in particular for formula (I), and the other symbols are as follows:
y e is identical or different on each occurrence and is B(Re)、C(Re)2、Si(Re)2、Ge(Re)2、C＝O、C＝NRe、C＝C(Re)2、O、S、S＝O、SO2、N(Re)、P(Re) or P (=o) R e, preferably N (R e)、O、S、B(Re)、C(Re)2 or Si (R e)2, more preferably N (R e), O or S;
j is 0, 1 or 2;
n is 0, 1, 2 or 3, preferably 0, 1 or 2;
m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2;
l is 0, 1,2,3, 4 or 5, preferably 0, 1 or 2.
Preference is given here to structures/compounds of the formulae (III-1), (III-2), (III-5), (III-7), (III-9), (III-10), (III-13), (III-15), (III-21), (III-23), (III-25), particularly preferably structures/compounds of the formulae (III-1), (III-2), (III-5), (III-9) and (III-10), very particularly preferably structures/compounds of the formulae (III-1), (III-2), (III-9).
The sum of the labels j, m, n and l in the structures/compounds of the formulae (III-1) to (III-32) is preferably not more than 6, particularly preferably not more than 4, more preferably not more than 2.
When two groups, which may in particular be selected from R, R a、Rb、Rc、Rd、Re、R1 and/or R 2, form a ring system with each other, the ring system may be a mono-or polycyclic aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system. In this case, the groups together forming the ring system may be adjacent, meaning that the groups are bonded to the same carbon atom or to carbon atoms directly bonded to each other, or they may be further apart from each other.
In a preferred embodiment of the application, it is possible that at least two preferably adjacent R a、Rb、Rc、Rd、Re groups together with the other groups to which the two R a、Rb、Rc、Rd、Re groups are bonded form a fused ring. In a preferred configuration it is possible to form the ring structures described in document WO2022/079068A1 filed by the European patent office on day 10 and 13 of 2021 under application number PCT/EP2021/078240, the fused ring structures shown in these documents and the descriptions described by the ring elements of formulae (RA-1) to (RA-12), (RA-1 a) to (RA-4 f) and/or (RB) in pages 37 to 40 of document WO2022/079068A1 for the purpose of disclosure are incorporated herein by reference. The ring structures detailed above, which are shown in detail in document WO2022/079068A1 and which preferably comprise ring elements of the formulae (RA-1) to (RA-12) and (RA-1 a) to (RA-4 f), particularly lead to the structures/compounds according to the application having surprisingly low refractive indices.
It is also possible that substituents R, R a、Rb、Rc、Rd、Re、R1 and R 2 according to the above formula do not form a fused aromatic or heteroaromatic ring system with the ring atoms of the ring system to which substituents R, R a、Rb、Rc、Rd、Re、R1 and R 2 are bonded, more preferably do not form any ring system with the ring atoms of the ring system to which substituents R, R a、Rb、Rc、Rd、Re、R1 and R 2 are bonded. This includes forming a fused aromatic or heteroaromatic ring system with the possible substituents R 2 which may be bonded to the substituents R a、Rb、Rc、Rd、Re and R 1.
It is also possible that at least one R c、Rd、Re group is identical or different on each occurrence and is selected from H, D, a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms or an aromatic or heteroaromatic ring system selected from the group of the formulae Ar-1 to Ar-76, or that R c、Rd、Re groups are identical or different on each occurrence and are selected from H, D or an aromatic or heteroaromatic ring system selected from the group of the formulae Ar-1 to Ar-76, and/or Ar' groups are identical or different on each occurrence and are selected from the group of the formulae Ar-1 to Ar-76,
Wherein R 1 has the definition given above, the dotted bond represents the bond to the corresponding group, and furthermore:
ar 1 is identical or different on each occurrence and is a divalent aromatic or heteroaromatic ring system having from 6 to 18 aromatic ring atoms and which may be substituted in each case by one or more R 1 groups;
A is identical or different on each occurrence and is C (R 1)2、NR1, O or S;
p is 0 or 1, wherein p=0 means that the Ar 1 group is absent and the corresponding aromatic or heteroaromatic group is directly bonded to the corresponding group;
q is 0 or 1, where q=0 means that no a group is bonded at this position and the R 1 group is bonded to the corresponding carbon atom.
Here, the structure of formula (Ar-1)、(Ar-2)、(Ar-3)、(Ar-12)、(Ar-13)、(Ar-14)、(Ar-15)、(Ar-16)、(Ar-40)、(Ar-41)、(Ar-42)、(Ar-43)、(Ar-44)、(Ar-45)、(Ar-46)、(Ar-69)、(Ar-70)、(Ar-76) is preferable, and the structures of formulae (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15) and (Ar-16) are particularly preferable.
When the above groups for the structures of formulas (Ar-1) to (Ar-76) have two or more A groups, all combinations from the definition of A are included for these possible options. Preferred embodiments in this case are those in which one a group is NR 1 and the other a group is C (R 1)2 or where both a groups are NR 1 or both a groups are O.
When a is NR 1, the substituent R 1 bonded to the nitrogen atom is preferably an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms and which may also be substituted by one or more R 2 groups. In a particularly preferred embodiment, the R 1 substituents are identical or different on each occurrence and are aromatic or heteroaromatic ring systems having from 6 to 24 aromatic ring atoms, in particular from 6 to 18 aromatic ring atoms, which do not have any fused aryl groups and any fused heteroaryl groups in which two or more aromatic or heteroaromatic 6-membered ring groups are directly fused to one another, and which may also be substituted in each case by one or more R 2 groups. Phenyl, biphenyl, terphenyl, and tetrabiphenyl are preferred. Also preferred are triazines, pyrimidines and quinazolines as set forth above for Ar-47 to Ar-50, ar-57 and Ar-58, wherein these structures may be substituted with one or more R 2 groups instead of R 1.
When A is C (R 1)2, the substituents R 1 bound to the carbon atoms are preferably identical or different on each occurrence and are straight-chain alkyl radicals having from 1 to 10 carbon atoms or branched or cyclic alkyl radicals having from 3 to 10 carbon atoms or aromatic or heteroaromatic ring systems having from 5 to 24 aromatic ring atoms, which may also be substituted by one or more R 2 groups, most preferably R 1 is a methyl group or a phenyl group, in which case the R 1 groups together may also form a ring system, which results in a spiro ring system.
Preferred R c、Rd and R e groups are described next.
In a preferred embodiment of the invention, R c、Rd and R e are identical or different in each case and are selected from H, D, F, CN, NO 2,Si(R1)3,B(OR1)2, straight-chain alkyl groups having from 1 to 20 carbon atoms or branched or cyclic alkyl groups having from 3 to 20 carbon atoms, where the alkyl groups can in each case be substituted by one or more R 1 groups or aromatic or heteroaromatic ring systems having from 5 to 60 aromatic ring atoms, preferably from 5 to 40 aromatic ring atoms, and in each case can be substituted by one or more R 1 groups.
In a further preferred embodiment of the invention, the radicals R c、Rd and R e are identical or different in each case and are selected from H, D, F, straight-chain alkyl radicals having from 1 to 20 carbon atoms or branched or cyclic alkyl radicals having from 3 to 20 carbon atoms, where the alkyl radicals can in each case be substituted by one or more R 1 radicals or aromatic or heteroaromatic ring systems having from 5 to 60 aromatic ring atoms, preferably from 5 to 40 aromatic ring atoms, and in each case can be substituted by one or more R 1 radicals.
It is also possible that at least one R c、Rd and R e radical, preferably one substituent R c、Rd and R e, is identical or different in each case and is selected from H, D, an aromatic or heteroaromatic ring system having from 6 to 30 aromatic ring atoms and which may be substituted by one or more R 1 radicals, or an N (Ar') 2 radical, more preferably at least one substituent R c、Rd and R e is identical or different in each case and is selected from aromatic or heteroaromatic ring systems having from 6 to 30 aromatic ring atoms and which may be substituted by one or more R 1 radicals. In another preferred embodiment of the invention, the substituents R c、Rd and R e form a fused ring, or the R c、Rd and R e groups are identical or different in each case and are selected from H, D, aromatic or heteroaromatic ring systems having 6 to 30 aromatic ring atoms and which may be substituted by one or more R 1 groups, or N (Ar') 2 groups. More preferably, the radicals R c、Rd and R e, preferably the substituents R c、Rd and R e, are identical or different in each case and are selected from H, or have from 6 to 24 aromatic ring atoms, Aromatic or heteroaromatic ring systems having from 6 to 18 aromatic ring atoms, more preferably from 6 to 13 aromatic ring atoms, and in each case may be substituted by one or more R 1 groups.
It is also possible that at least one of the R c、Rd and R e groups is selected from the structures of the following formula (Het-I):
Wherein the dotted bond represents the bond to the corresponding group, and the additional symbols are as follows:
W 3、W4 is identical or different on each occurrence and is-C (R 3)2-(Y1)n-C(R3)2 -group, is-C (R 1)＝C(R1) -group or is an ortho-linked aromatic or heteroaromatic ring system which has from 5 to 60 aromatic ring atoms and can be substituted by one or more R 1 groups;
Y 1 is identical or different on each occurrence and is selected from C (R 1)2、C(R1)2-C(R1)2、C(R1)＝C(R1), where R 1 has the definition given above, in particular for formula (I), and
R 3 is identical or different in each case and is a straight-chain alkyl, alkoxy or thioalkoxy radical having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy radical having 3 to 40 carbon atoms or an alkenyl radical having 2 to 40 carbon atoms, which radicals may each be substituted by one or more R 2 radicals, where one or more non-adjacent CH 2 radicals may be replaced by -R2C＝CR2-、-C≡C-、Si(R2)2、Ge(R2)2、C＝O、C＝S、C＝Se、C＝NR2、-C(＝O)O-、-C(＝O)NR2-、NR2、P(＝O)(R2)、-O-、-S-、SO or SO 2, and where one or more hydrogen atoms may be replaced by D, F, cl, br, I, CN or NO 2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and which may in each case be substituted by one or more R 2 radicals, or an aryloxy or heteroaryloxy radical having 5 to 60 aromatic ring atoms and which may be substituted by one or more R 2 radicals, or an aralkyl or heteroarylalkyl radical having 5 to 60 aromatic ring atoms and which may be substituted by one or more R 2 radicals, or a combination of these radicals, where two or more R groups together may form, in particular, preferably together with one or more R 2 and one or more R 2 may form part of the radicals, especially the radicals defined for R 2.
It is preferred if at least one of the groups W 3、W4 is a-C (R 3)2-(Y1)n-C(R3)2 -group).
In a preferred configuration, it is possible that at least one of the radicals R c、Rd and R e, preferably at least one of the radicals R d and R e, more preferably at least one of the radicals R e, is selected from the structures of the formulae (Het-II) to (Het-XIX),
Wherein the symbols R 1 and R 3 have the definitions given above, in particular for the formulae (I) or (Het-I), V 1 is B (R 1)、C(R1)2、Si(R1)2、N(R1), O, S, preferably C (R 1)2、Si(R1)2、N(R1), O, and X 1 is N or C (R 1), preferably C (R 1).
Here, the structures of the formulae (Het-II) to (Het-V) are preferred, the structure of the formula (Het-XIX) is particularly preferred, and the structure of the formula (Het-II) is very particularly preferred.
It is preferably possible that the R 3 radicals are identical or different in each case and are selected from the group consisting of straight-chain alkyl, alkoxy or thioalkoxy radicals having 1 to 40 carbon atoms, or branched or cyclic alkyl, alkoxy or thioalkoxy radicals having 3 to 40 carbon atoms, or alkenyl radicals having 2 to 40 carbon atoms, which radicals may each be substituted by one or more R 2 radicals, where one or more non-adjacent CH 2 radicals may be replaced by -R2C＝CR2-、-C≡C-、Si(R2)2、Ge(R2)2、C＝O、C＝S、C＝Se、C＝NR2、-C(＝O)O-、-C(＝O)NR2-、NR2、P(＝O)(R2)、-O-、-S-、SO or SO 2, and where one or more hydrogen atoms may be replaced by D, F, cl, br, I, CN or NO 2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and in each case being substituted by one or more R 2 radicals, or an aryloxy or heteroaryloxy radical having 5 to 60 aromatic ring atoms and being substituted by one or more R 2 radicals, or an aralkyloxy radical having 5 to 60 aromatic ring atoms and being substituted by one or more R 2 radicals, where two or more R 2 may form a combination of the radicals, preferably together with one another R 2, R 2 may form part of the radicals, or a combination of the radicals, preferably two or more radicals, R 2 being defined above, and one or more radicals may be taken together.
Other preferences for the groups shown in the structures of formulae (Het-I) to (Het-XIX) will be apparent from the description of the compounds of the invention in which the W 1、W2、X、V、Ra、Rb、Rc、Rd and R e groups shown in formulae (I) and (I-1) to (I-18) should be replaced by W 3、W4、X1、V1、R1 and R 3 groups, respectively. Particularly preferred groups result from structures/compounds of the formulae (II-1) to (II-8) or (III-1) to (III-32), respectively, wherein the X e and Y e groups should be adjusted accordingly here, so that the R e groups of these groups should be replaced by R 1 groups. Particularly preferred R 3 groups will be apparent from the description of the R a and R b groups, wherein the R 1 groups of these groups should be replaced by R 2 groups.
It is also possible that at least one of the R c、Rd and R e groups is an aromatic or heteroaromatic ring system having 5 to 13 aromatic ring atoms and which may be substituted by one or more R 1 groups.
Preferably, where applicable, at least one group, preferably one substituent R c、Rd and R e, is selected from phenyl, biphenyl, terphenyl, tetrabiphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or biphenylene, each of which may be substituted with one or more R 1 groups. The expression "substituent" here more particularly means that R c、Rd and R e are not H, preferably are not H and are not D. Furthermore, if two or more substituents selected from the mentioned aromatic or heteroaromatic groups are present, the substituents R c、Rd and R e may be identical or different.
Preferred aromatic or heteroaromatic ring systems represented by the groups R, R a、Rb、Rc、Rd and R e or Ar' are selected from phenyl, biphenyl, especially ortho-, meta-or para-biphenyl, terphenyl, especially ortho-, meta-, or para-terphenyl or branched terphenyl, tetrabiphenyl, especially ortho-, meta-, or para-or branched tetrabiphenyl, fluorenes which can be linked via the 1-, 2-, 3-, or 4-position, spirobifluorenes which can be linked via the 1-, 2-, 3-, or 4-position, naphthalenes, especially 1-or 2-bonded naphthalenes, indoles, benzofurans, benzothiophenes, carbazoles which can be linked via the 1-, 2-, 3-, or 4-position, dibenzothiophenes which can be linked via the 1-, 2-, 3-, or 4-position, indenocarbazoles, indolocarbazoles, pyridines, pyrimidines, pyrazines, pyridazines, triazines, quinolines, isoquinolines, quinazolines, quinoxalines, and quinoxalines, which can each be substituted by one or more R35 or R35. Particularly preferred aromatic or heteroaromatic ring systems which may be represented by R, R a、Rb、Rc、Rd and R e or Ar' groups are the structures (Ar-1) to (Ar-76) detailed above, preferably the structures of the formulae (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16), (Ar-69), (Ar-70), (Ar-76), particularly preferably the structures of the formulae (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16). With respect to structures (Ar-1) through (Ar-76), it should be noted that these structures are shown with the possible substituents R 1. In the case of ring systems Ar, these possible substituents R 1 should be replaced by R e.
Other suitable R c、Rd and R e groups are groups of the formula-Ar 4-N(Ar2)(Ar3), in which Ar 2、Ar3 and Ar 4 are identical or different in each case and are aromatic or heteroaromatic ring systems having from 5 to 24 aromatic ring atoms and in each case being substituted by one or more R 1 groups. Here the total number of aromatic ring atoms in Ar 2、Ar3 and Ar 4 is not more than 60, preferably not more than 40.
Here, ar 4 and Ar 2 may also be bonded to each other by a single bond or a group selected from C (R 1)2、NR1, O, or S), and/or Ar 2 and Ar 3 may also be bonded to each other by a single bond or a group selected from C (R 1)2、NR1, O, or S).
Preferably, ar 4 is an aromatic or heteroaromatic ring system having from 6 to 24 aromatic ring atoms, preferably from 6 to 12 aromatic ring atoms, and in each case optionally substituted by one or more R 1 groups. More preferably, ar 4 is selected from the group consisting of an o-, m-or p-phenylene subunit or an o-, m-or p-biphenyl, each of which may be substituted with one or more R 1 groups, but is preferably unsubstituted. Most preferably, ar 4 is an unsubstituted phenylene group.
Preferably, ar 2 and Ar 3 are identical or different in each case and are aromatic or heteroaromatic ring systems which have from 6 to 24 aromatic ring atoms and which may be substituted in each case by one or more R 1 groups. It is particularly preferred that the Ar 2 and Ar 3 radicals are identical or different in each case and are selected from benzene, ortho-, meta-or para-biphenyl, ortho-, meta-, or para-terphenyl or branched terphenyl, ortho-, meta-, or para-tetrabiphenyl or branched tetrabiphenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl or 4-fluorenyl, 1-spirobifluorenyl, 2-spirobifluorenyl, 3-spirobifluorenyl or 4-spirobifluorenyl, 1-naphthyl or 2-naphthyl, indole, benzofuran, benzothiophene, 1-carbazole, 2-carbazole, 3-carbazole or 4-carbazole, 1-dibenzofuran, 2-dibenzofuran, 3-dibenzofuran or 4-dibenzofuran, 1-dibenzothiophene, 3-dibenzothiophene or 4-dibenzothiophene, indenocarbazole, indole, 2-pyridine, 3-pyridine or 4-pyridine, 2-pyrimidine, 4-pyrimidine or 5-pyrimidine, pyrazine, or triazine, each of which may be substituted by one or more R 1. Most preferably Ar 2 and Ar 3 are identical or different in each case and are selected from benzene, biphenyl, in particular ortho-, meta-or para-biphenyl, terphenyl, in particular ortho-, meta-or para-terphenyl or branched terphenyl, tetrabiphenyl, in particular ortho-, meta-or para-or branched tetrabiphenyl, fluorene, in particular 1-fluorene, 2-fluorene, 3-fluorene or 4-fluorene, or spirobifluorene, in particular 1-spirobifluorene, 2-spirobifluorene, 3-spirobifluorene or 4-spirobifluorene.
The preferences set forth for the R c、Rd and R e groups also apply to the R a and R b groups due to the limitations specified in claim 1.
It is further possible that the R a groups bonded to one carbon atom are identical.
It is also possible that the R a groups bonded to different carbon atoms are identical.
It is also possible that the R a groups bound to different carbon atoms are different.
In a preferred configuration, it is possible that the R a groups bound to carbon atoms are selected from straight-chain alkyl groups having 1 to 10 carbon atoms or branched or cyclic alkyl groups having 3 to 10 carbon atoms, which groups may each be substituted by one or more R 1 groups, preferably may be deuterated, wherein two or more, preferably adjacent substituents R a together may form a ring system.
It is also possible that the R a groups bound to one carbon atom are selected from aromatic or heteroaromatic ring systems which have 5 to 20 aromatic ring atoms and which may in each case be substituted by one or more R 1 groups, and are preferably phenyl groups which may in each case be substituted by one or more R 1 groups, preferably may be deuterated, wherein two or more, preferably adjacent substituents R a together may form a ring system.
It is also possible that the R b groups bonded to one carbon atom are identical.
It is also possible that the R b groups bound to different carbon atoms are identical.
It is further possible that the R b groups bound to different carbon atoms are different.
In a preferred configuration, it is possible that the R b groups bound to carbon atoms are selected from straight-chain alkyl groups having 1 to 10 carbon atoms or branched or cyclic alkyl groups having 3 to 10 carbon atoms, which groups may each be substituted by one or more R 1 groups, preferably deuterated, wherein two or more, preferably adjacent substituents R a together may form a ring system.
It is also possible that the R b groups bound to one carbon atom are selected from aromatic or heteroaromatic ring systems which have 5 to 20 aromatic ring atoms and which may in each case be substituted by one or more R 1 groups, and are preferably phenyl groups which may in each case be substituted by one or more R 1 groups, preferably may be deuterated, wherein two or more, preferably adjacent substituents R b together may form a ring system.
It is also possible that the R a groups together with the preferably adjacent R b groups form an aliphatic or heteroaliphatic ring system which may be substituted by one or more R 1 groups, wherein the ring system preferably contains 3 to 10 carbon atoms.
In a further preferred embodiment of the invention, R 1 is identical or different on each occurrence and is selected from H, D, F, CN, a linear alkyl group having from 1 to 10 carbon atoms or a branched or cyclic alkyl group having from 3 to 10 carbon atoms, where the alkyl groups can in each case be substituted by one or more R 2 groups or an aromatic or heteroaromatic ring system having from 6 to 24 aromatic ring atoms and in each case can be substituted by one or more R 2 groups. In a particularly preferred embodiment of the invention, R 1 is identical or different on each occurrence and is selected from H, a straight-chain alkyl group having 1 to 6 carbon atoms, in particular having 1,2,3 or 4 carbon atoms, or a branched or cyclic alkyl group having 3 to 6 carbon atoms, where the alkyl group may be substituted by one or more R 2 groups, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system having 6 to 13 aromatic ring atoms and in each case may be substituted by one or more R 2 groups, but is preferably unsubstituted.
In a further preferred embodiment of the invention R 2 is identical or different on each occurrence and is H, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms, which groups may be substituted by alkyl groups having 1 to 4 carbon atoms, but are preferably unsubstituted.
Meanwhile, in the compound of the present invention treated by vacuum evaporation, the alkyl group preferably has not more than five carbon atoms, more preferably has not more than 4 carbon atoms, and most preferably has not more than 1 carbon atom. For compounds treated from solution, suitable compounds are also those substituted with alkyl groups having up to 10 carbon atoms, in particular branched alkyl groups, or with oligoarylene groups such as ortho-, meta-or para-or branched terphenyl or tetrabiphenyl groups.
In a preferred configuration, the structures/compounds of the present invention preferably have a high degree of deuteration. It is preferably possible that the degree of deuteration is at least 50%, preferably at least 80%, particularly preferably at least 90%, most preferably at least 95%. The degree of deuteration is determined by the numerical ratio (D/(d+h) ×100) of deuterium to the sum of deuterium and 1 H hydrogen. The compounds are particularly preferably fully deuterated.
The compounds of the invention are particularly suitable for use in blue-emitting electroluminescent devices. Depending on the layer, these require materials with high triplet energy levels. However, many substituents with fused aromatic or heteroaromatic groups can cause a reduction in triplet energy levels.
Therefore, a naphthyl structure is preferable to an anthracene structure. Furthermore, fluorenyl, spirobifluorenyl, dibenzofuranyl, and/or dibenzothienyl structures are preferred over naphthyl structures.
Unfused structures such as phenyl, biphenyl, terphenyl and/or tetralin structures are particularly preferred.
Even more preferably it is possible that either Ar or R groups do not contain anthracene groups, preferably none of Ar, R a、Rb、Rc、Rd、Re groups contain anthracene groups.
It is also very particularly preferably possible that the Ar or R groups do not comprise an aromatic or heteroaromatic ring system having three linearly fused aromatic 6-membered rings, wherein preferably none of the Ar, R a、Rb、Rc、Rd、Re groups comprise an aromatic or heteroaromatic ring system having three linearly fused aromatic 6-membered rings.
When the compounds of the invention are substituted with aromatic or heteroaromatic R a、Rb、Rc、Rd、Re、R1 or R 2 groups, it is preferred that these do not have any aryl or heteroaryl groups with more than two aromatic six-membered rings directly fused to each other. More preferably, the substituents are completely free of any aryl or heteroaryl groups having six membered rings directly fused to each other. The reason for this preference is the low triplet energy of such structures. Fused aryl groups according to the invention having more than two aromatic six-membered rings fused directly to each other but nevertheless having good suitability are phenanthrene and triphenylene, since they also have a high triplet energy level.
It is also possible that none of the Ar, R a、Rb、Rc、Rd and R e groups contain or form fluorenone groups, preferably none of the Ar, R a、Rb、Rc、Rd、Re、R1 and R 2 groups contain or form fluorenone groups. This includes substituents bonded to Ar, R a、Rb、Rc、Rd、Re groups, and the like. Fluorenones contain five membered rings with CO groups fused to two aromatic 6 membered rings.
When the compounds of formula (I) or the preferred embodiments are used as host materials for phosphorescent emitters or in layers directly adjoining phosphorescent layers, it is also preferred that the compounds do not comprise any fused aryl or heteroaryl groups in which more than two six-membered rings are directly fused to one another. Phenanthrenes and biphenylenes are exceptions because of their high triplet energy, which may be preferred despite the presence of fused aromatic six-membered rings.
In a preferred configuration of the invention, it is possible that the compound
Is excluded from the scope of protection.
It is also possible that the compounds comprise exactly two, exactly three or exactly four structures of the formulae (I), (I-1) to (I-18), (II-1) to (II-8) and/or (III-1) to (III-32).
In a preferred configuration, the compound is selected from the group consisting of compounds of formula (D-1),
Wherein the L 1 group is a linking group, preferably a bond or an aromatic or heteroaromatic ring system having 5 to 40, preferably 5 to 30, aromatic ring atoms and which may be substituted by one or more R e groups, and the other symbols used have the definitions given above, in particular for formula (I), wherein the L 1 group forms a bond to the base structure instead of a hydrogen atom or substituent, preferably the L 1 group is bonded to the Z, W 1、W2 group, preferably to the Z group. It is further possible that the Z group which can be bonded to the L 1 group is also shared by the two base structures, so that the compound of formula (D1) has only one Z group and L 1 is given by this Z group.
In a further preferred embodiment of the invention, L 1 is a bond or an aromatic or heteroaromatic ring system having 5 to 14 aromatic or heteroaromatic ring atoms, preferably an aromatic ring system having 6 to 12 carbon atoms, which ring system may be substituted, but is preferably unsubstituted, with one or more R e groups, wherein R e may have the definition given above, in particular for formula (I). More preferably, L 1 is an aromatic ring system having 6 to 10 aromatic ring atoms or a heteroaromatic ring system having 6 to 13 heteroaromatic ring atoms, each of which may be substituted by one or more R 1 groups, but is preferably unsubstituted, wherein R 1 may have the definition given above, in particular for formula (I).
It is also preferred that the symbol L 1 shown in formula (D1) is identical or different in particular in each case and is a bond or an aryl or heteroaryl group having from 5 to 24 ring atoms, preferably from 6 to 13 ring atoms, more preferably from 6 to 10 ring atoms, so that the aromatic or heteroaromatic group of the aromatic or heteroaromatic ring system is bonded directly, i.e. via an atom of the aromatic or heteroaromatic group, to the corresponding atom of the other group.
It is also possible that the L 1 group shown in formula (D1) comprises an aromatic ring system having no more than four, preferably no more than three, more preferably no more than two fused aromatic and/or heteroaromatic 6-membered rings, preferably does not comprise any fused aromatic or heteroaromatic ring system.
Examples of suitable aromatic or heteroaromatic ring systems L 1 are selected from the group consisting of o-, m-or p-biphenylene, terphenylene, especially branched terphenylene, tetrabenzylene, especially branched tetrabiphenyl, fluorenylene, spirobifluorenylene, dibenzofuranylene, dibenzothiophenylene, and carbazole, each of which may be substituted, but preferably unsubstituted, by one or more R 1 groups.
In a preferred configuration, the compounds of the present invention may be represented by at least one of the structures of formulas (I), (I-1) to (I-18), (II-1) to (II-8) and/or (III-1) to (III-32). Preferably, the molecular weight of the compounds according to the invention comprising the structures of the formulae (I), (I-1) to (I-18), (II-1) to (II-8) and/or (III-1) to (III-32) is not more than 5000g/mol, preferably not more than 4000g/mol, particularly preferably not more than 3000g/mol, particularly preferably not more than 2000g/mol, more particularly preferably not more than 1200g/mol, most preferably not more than 900g/mol.
Furthermore, one feature of the preferred compounds of the present invention is that they are sublimable. The molar mass of these compounds is generally less than about 1200g/mol.
It is also possible that the compound comprising the structure of formula (I), preferably the compound of formula (I) or a preferred embodiment of the structure/compound is not in direct contact with a metal atom and is preferably not a ligand of a metal complex.
The above-mentioned preferred embodiments can be combined with each other as desired within the limits defined in claim 1. In a particularly preferred embodiment of the invention, the above-mentioned preferences occur simultaneously.
Examples of preferred compounds according to the embodiments detailed above are the compounds detailed in the table below:
the basic structure of the compounds of the present invention can be prepared by the routes outlined in the schemes below. The individual synthetic steps here, for example coupling reactions which lead to the formation of C-C bonds and/or C-N bonds, are known in principle to the person skilled in the art. These include the Buchwald (BUCHWALD), ringer wood (SUZUKI), YAMAMOTO (YAMAMOTO), stahler (STILLE), herke (HECK), root bank (NEGISHI), head of China (SONOGASHIRA), and juniper mountain (HIYAMA) reactions.
Additional information about the synthesis of the compounds of the present invention can be found in the synthesis examples.
The following schemes describe the preparation of the compounds of formulae (I-1), (I-2) and (I-3) of the present invention by way of example, such that other compounds of the present invention, especially those of formulae (I-4) to (I-18), can be obtained starting from different parent structures by similar synthetic routes. Those skilled in the art will use the corresponding amine compounds for preparing the compounds of formulas (I-4) through (I-18).
For example, the compounds of the invention can be prepared in four steps from synthetic units known in the literature, tetra-substituted 1, 2-diaminoethane (1) and 2-fluoronitrobenzene or 2-chloronitrobenzene (2) (wherein X: CR) or N-heterocyclic analogues (X: CR and at least one x=n) (see scheme 1).
Firstly, according to this scheme, tetra-substituted 1, 2-diaminoethane is reacted with 2-fluoronitrobenzene or 2-chloronitrobenzene in a bipolar aprotic medium such as Dimethylformamide (DMF), dimethylacetamide (DMAc), N-methylpyrrolidone (NMP), dimethylsulfoxide (DMSO), acetonitrile, optionally with the addition of a sterically demanding base such as Hunig's base in nucleophilic aromatic substitution to form C-N bonds, to give an ortho-nitroarylamine (3) (step 1); see, for example, P.Zhang et al, J.Med. Chem.,2009,52 (18), 5703. Subsequently, the nitro group is reduced to an amino group by means of hydrogen/platinum (IV) oxide or Pd/C to give triamine (4) (step 2); see, for example, J.A. Pollock et al Tetrahedron Letters,2015,56,6097. The triamine (4) is preferably reacted with phosgene in Dichloromethane (DCM) to give the amide (see M.T.Bl zquez et al, heterycles, 2006,69,73-or also using triphosgene or trialkylchloroformate or alkyl carbonate) which is then dehydrated in situ with polyphosphoric acid to give guanidine (5) (see WO 2012/130709). Finally, guanidine (5) is preferably reacted with aryl or heteroaryl halides or triflates Ar/HetArX (x= F, cl, br, I, OTf) to afford the compounds (6 a) and (6 b) according to the invention by means of a bloc-haltmann coupling or nucleophilic aromatic substitution (see, for example, WO 2012/130709). The isomer compounds (6 a) and (6 b) can be isolated by standard methods (chromatography, fractional crystallization).
Scheme 1:
similarly, compound (10) of the present invention can be prepared by first reacting tetra-substituted 1, 2-diaminoethane (1) with 2, 3-tetraalkylaziridine (7) known in the literature to prepare triamine (8); see scheme 2. Other compounds of the invention are obtained via the corresponding amine compounds.
The triamine (8) is preferably reacted with phosgene in Dichloromethane (DCM) to give the amide (see M.T. Bl zquez et al, heteromycles, 2006,69,73-alternatively triphosgene or trialkylchloroformate or alkyl carbonate may be used) which is then dehydrated in situ with polyphosphoric acid to give guanidine (9) (see WO 2012/130709). Finally, guanidine (9) is preferably reacted with aryl or heteroaryl halides or triflates Ar/HetArX (x= F, cl, br, I, OTf) to afford compound (10) of the invention by bloc-haltmah, ullmann coupling or nucleophilic aromatic substitution (see, for example, WO 2012/130709). If all R groups are identical, the result is compound (10) in isomerically pure form, and if the R groups in reactants (1) and (7) are chosen differently, two isomeric compounds (10 a and 10 b) are obtained analogously to scheme 1, which in turn can be separated by standard methods (chromatography, fractional crystallization).
Scheme 2:
The compounds (6) according to the invention can be further functionalized, for example by regioselective bromination (see WO 2014/009317) followed by conversion of the bromides thus obtained in C-C or C-N coupling reactions, for example in Suzuki, root bank, grignard-Cross, celaster, buch-Hartmann, ullman couplings, see scheme 3.
Scheme 3:
the definition of the symbols used in the schemes presented above essentially corresponds to the definition for formula (I), and the numbering and complete representation of all symbols is omitted for the sake of clarity.
Accordingly, the present invention also provides a process for preparing the compounds of the invention, wherein a basic skeleton having amino groups is synthesized and at least one aromatic or heteroaromatic group is introduced, preferably by nucleophilic aromatic substitution or coupling reactions.
For reasons of completeness, it is pointed out that structures of the formulae (I-2) and (I-3), for example, can in many cases be converted into one another by rearrangement at high temperatures. These mixtures may be isolated or used as such. This also applies to the other isomers. The mixtures obtained or formed by rearrangement herein can be used to produce electronic devices as described above and described in more detail later.
By these methods, if necessary, subsequent purification, for example recrystallisation or sublimation, is possible, so that the compounds according to the invention can be obtained in high purity, preferably greater than 99% (determined by means of 1 H-NMR and/or HPLC).
The compounds of the invention may also be mixed with polymers. Also, these compounds can be covalently incorporated into the polymer. This is particularly useful for compounds substituted with a reactive leaving group such as bromine, iodine, chlorine, boric acid or a borate or substituted with a reactive polymerizable group such as an alkene or oxetane. These find use as monomers in the manufacture of the corresponding oligomers, dendrimers or polymers. The oligomerization or polymerization is preferably effected via halogen functions or boric acid functions or via polymerizable groups. The polymers can furthermore be crosslinked via such groups. The compounds and polymers of the present invention may be used in the form of crosslinked or uncrosslinked layers.
Thus, the present invention also provides an oligomer, polymer or dendrimer containing one or more of the structures of formula (I) as described in detail above and preferred embodiments of the formula or compounds of the invention wherein there is a bond to the polymer, oligomer or dendrimer of one or more of the structures of the formula or compounds of the invention and preferred embodiments of the formula. According to the structure of formula (I) and the preferred embodiment of this formula or the linking of the compounds, these thus form side chains or linkages of the oligomer or polymer within the main chain. The polymer, oligomer or dendrimer may be conjugated, partially conjugated or non-conjugated. The oligomer or polymer may be linear, branched or dendritic. The same preferences as described above apply to the repeat units of the compounds of the invention in oligomers, dendrimers and polymers.
To prepare the oligomer or polymer, the monomers of the invention are homopolymerized or copolymerized with other monomers. Preference is given to copolymers in which the units of the formula (I) or of the preferred embodiments described above and below are present in the range from 0.01 mol% to 99.9 mol%, preferably from 5 mol% to 90 mol%, more preferably from 20 mol% to 80 mol%. Suitable and preferred comonomers forming the polymer base skeleton are selected from fluorene (e.g. according to EP 842208 or WO 2000/022026), spirobifluorene (e.g. according to EP 707020, EP 894107 or WO 2006/061181), p-phenylene (e.g. according to WO 92/18552), carbazole (e.g. according to WO 2004/070772 or WO 2004/113468), thiophene (e.g. according to EP 1028136), dihydrophenanthrene (e.g. according to WO 2005/014689), cis-and trans-indenofluorene (e.g. according to WO 2004/04901 or WO 2004/113412), ketone (e.g. according to WO 2005/040302), phenanthrene (e.g. according to WO 2005/104264 or WO 2007/017066) or other various these units. The polymers, oligomers and dendrimers may also contain other units, for example hole transporting units, especially those based on triarylamines, and/or electron transporting units.
In addition, of particular interest are the compounds of the invention which are characterized by a high glass transition temperature. In this respect, particular preference is given to the compounds according to the invention comprising the structure of the formula (I) or the preferred embodiments described above and below, having a glass transition temperature, measured in accordance with DIN 51005 (2005-08 edition), of at least 70 ℃, more preferably at least 110 ℃, even more preferably at least 125 ℃, particularly preferably at least 150 ℃.
In order to treat the compounds of the invention from the liquid phase, for example by spin coating or by printing methods, formulations of the compounds of the invention are required. These formulations may be, for example, solutions, dispersions or emulsions. For this purpose, a mixture of two or more solvents may be preferably used. Suitable and preferred solvents are, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, THF, methyl-THF, THP, chlorobenzene, diAlkyl, phenoxytoluene, in particular 3-phenoxytoluene, (-) -fenchyl, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3, 4-dimethylbenzene, 3, 5-dimethylbenzene, acetophenone, α -terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, NMP, 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-bis (3, 4-dimethylbenzene), 2-methylbenzene, 2-methyl-biphenyl, 1-ethyl-hexanoate, ethyl-octanoate, ethyl-1-hexanoate, n-octanoate, n-ethyl-hexanoate, n-octanoate, mixtures thereof.
Accordingly, the present invention also provides a formulation or composition comprising at least one compound of the present invention and at least one other compound. The other compound may be, for example, a solvent, in particular one of the solvents mentioned above or a mixture of these solvents. If the other compound comprises a solvent, the mixture is referred to herein as a formulation. The other compound may alternatively be at least one other organic or inorganic compound as well used in electronic devices, such as a luminescent compound and/or other host material. It is preferably possible that the at least one further compound is selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF, host materials, electron transport materials, electron injection materials, hole conducting materials, hole injection materials, electron blocking materials and hole blocking materials, preferably host materials.
The invention also provides the use of the compounds according to the invention in electronic devices, in particular in organic electroluminescent devices. It is preferable that the compound of the present invention is used as a host material, an electron transport material, an electron injection material, a hole conduction material, a hole injection material, an electron blocking material, a hole blocking material in an electronic device, where applicable.
It is further possible that the compound of the present invention is used as a host material, an electron transporting material, an electron injecting material or a hole blocking material, and that the compound of the present invention comprises at least one electron transporting group and/or one electron withdrawing group, wherein preferred electron transporting groups and/or electron withdrawing groups have been defined above.
It is also possible that the compounds of the present invention are used as host materials, hole conducting materials, hole injecting materials or electron blocking materials, and that the compounds of the present invention comprise at least one hole transporting group, wherein preferred hole transporting groups have been defined above.
It is also possible that the compounds of the invention are used as host materials and comprise at least one hole-transporting group and at least one electron-transporting and/or electron-withdrawing group, wherein preferred hole-transporting, electron-transporting and/or electron-withdrawing groups have been defined above.
The present invention still further provides an electronic device comprising at least one compound of the present invention. An electronic device in the context of the present invention is a device comprising at least one layer comprising at least one organic compound. The assembly may also contain inorganic materials or other layers formed entirely of inorganic materials.
The electronic device is more preferably selected from the group consisting of organic electroluminescent devices (OLED, sOLED, PLED, LEC, etc.), preferably Organic Light Emitting Diodes (OLEDs), small molecule based organic light emitting diodes (sOLED), polymer based organic light emitting diodes (PLEDs), light emitting electrochemical cells (LECs), organic laser diodes (O-lasers), organic plasma light emitting devices (d.m. koller et al, nature Photonics 2008, 1-4), organic integrated circuits (O-ICs), organic field effect transistors (O-FETs), organic thin film transistors (O-TFTs), organic light emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field quench devices (O-FQDs), and organic electrical sensors, preferably organic electroluminescent devices (OLED, sOLED, PLED, LEC, etc.), more preferably Organic Light Emitting Diodes (OLEDs), small molecule based organic light emitting diodes (sOLED), polymer based organic light emitting diodes (eds), especially phosphorescent OLEDs.
The organic electroluminescent device comprises a cathode, an anode and at least one light emitting layer. In addition to these layers, the organic electroluminescent device may also comprise further layers, for example in each case one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers and/or charge generation layers. An intermediate layer having, for example, an exciton blocking function can likewise be introduced between the two light-emitting layers. However, it should be noted that each of these layers does not necessarily exist. In this case, the organic electroluminescent device may contain one light emitting layer, or it may contain a plurality of light emitting layers. If a plurality of light-emitting layers are present, it is preferable that these light-emitting layers have a plurality of light-emitting peaks between 380nm and 750nm in total, so that the overall result is white light emission, in other words, a plurality of light-emitting compounds which can emit fluorescence or phosphorescence are used in the light-emitting layers. Particularly preferred are systems with three light-emitting layers, wherein the three layers show blue, green and orange or red light emission. The organic electroluminescent device of the invention may also be a tandem electroluminescent device, in particular a white-emitting OLED.
The compounds of the invention can be used in different layers depending on the exact structure. Preferably, the organic electroluminescent device comprises the compound of formula (I) or the preferred embodiments described above in the light-emitting layer as host material for fluorescent, phosphorescent or luminophores exhibiting TADF (thermally activated delayed fluorescence), in particular for phosphorescent luminophores. Furthermore, the compounds of the present invention can also be used in electron transport layers, electron injection layers and/or hole transport layers, hole injection layers and/or exciton blocking layers and/or hole blocking layers. More preferably, the compounds of the invention are used as host materials for phosphorescent emitters in the light-emitting layer, in particular for red, orange, green, yellow or blue phosphorescent emitters, as electron-transporting or hole-blocking materials in the electron-transporting or hole-blocking layer, or as hole-transporting or electron-blocking materials in the hole-transporting or electron-blocking layer. The applicability of the various compounds of formula (I) has been shown above in connection with preferred uses.
When the compound of the present invention is used as a host material for a phosphorescent compound in a light-emitting layer, it is preferably used in combination with one or more phosphorescent materials (triplet emitters).
In the context of the present application phosphorescence is understood to mean luminescence from an excited state in which the spin multiplex state is higher, i.e. the spin state >1, in particular luminescence from an excited triplet state. In the context of the present application, all luminescent complexes with transition metals or lanthanides, in particular all iridium, platinum and copper complexes, should be regarded as phosphorescent compounds.
The mixture of the compounds according to the invention with the luminescent compounds contains between 99 and 1% by volume, preferably between 98 and 10% by volume, more preferably between 97 and 60% by volume, in particular between 95 and 80% by volume, based on the total mixture of the luminescent body and the matrix material. Accordingly, the mixture contains between 1 and 99% by volume, preferably between 2 and 90% by volume, more preferably between 3 and 40% by volume, in particular between 5 and 20% by volume, of the luminophore, based on the total mixture of luminophore and matrix material.
In one embodiment of the invention, the compounds of the invention are used herein as the sole matrix material for phosphorescent emitters ("unitary body").
Another embodiment of the present invention is the use of a compound of the present invention in combination with other host materials as a host material for phosphorescent emitters. Suitable matrix materials which can be used in combination with the compounds of the invention are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, for example according to WO 2004/013080, WO 2004/093207, WO 2006/005627 or WO 2010/006680; triarylamines; carbazole derivatives, such as CBP (N, N-dicarbazolyl biphenyl) or carbazole derivatives disclosed in WO 2005/039246, US2005/0069729, JP 2004/288381, EP 1205527, WO 2008/086851 or WO 2013/04176; indolocarbazole derivatives, for example according to WO 2007/063272 or WO 2008/056746, indenocarbazole derivatives, for example according to WO 2010/136109, WO 2011/000455, WO 2013/04176 or WO 2013/056776, azacarbazole derivatives, for example according to EP 1617710, EP 1617711, EP 1731584, JP 2005/347160, bipolar matrix materials, for example according to WO 2007/137725, silanes, for example according to WO 2005/111172, borazopentalene or borate esters, for example according to WO 2006/1170552, triazine derivatives, for example according to WO 2007/063276, WO 2008/056746, WO 2010/015306, WO 2011/060859 or WO 2011/060877, zinc complexes, for example according to EP 652273 or WO 2009/062578, silazopentalene derivatives, for example according to WO 2010/054729, phosphazene derivatives, for example, bridge-like WO 2010/05473/2012, for example, or bridge derivatives of WO 2012/WO 2012, for example, WO 2012/WO 2012/WO scid, WO's, WO 2012/052012/WO' i, WO scid, WO 2016/060, WO 2016, WO 060/05779 or WO 060, or WO 201060, WO 201's, or WO 201201201201's, or WO 201201201/060, or WO 2012016, or/2012012016, or/201201201201/201, or/201/201 201201/201201201201201201201201201201201201pro or// 060/060201201201pro or/060060060pro or/060pro or/060/060pro or/060060pro or/060pro or/060 060pro or/060060pro or/060060060060060060060060060060pro or 060060060060pro or 060060060060060060060060or 060060060060/or 060060060060or 060or 060060060060060or 060060060060060060060060060060or 060060060060060060060060060060060060060060or 060060060060060060060060060060060060060060060060060060060060060060, for example according to WO 2012/048781, dibenzofuran derivatives, for example according to WO 2015/169412, WO 2016/015810, WO 2016/023608, WO 2017/148564 or WO 2017/148565, or biscarbazoles, for example according to JP 3139321B 2.
In a preferred configuration, the compound used as host material containing the structure/compound of formula (I) or the preferred embodiments detailed above is preferably combined with one or more phosphorescent materials (triplet emitters) and/or compounds of TADF (thermally activated delayed fluorescence) host material. The formation of a superfluorescent system as described in WO 2012/133188 and/or a superphosphorescent system as described in US 2017271611 is preferred here. This combination is a preferred embodiment according to the invention.
WO 2015/091716 A1 and WO 2016/193243 A1 disclose OLEDs containing both phosphorescent compounds and fluorescent emitters in the light-emitting layer, wherein energy is transferred from the phosphorescent compounds to the fluorescent emitters (superphosphorescence). In this case, the phosphorescent compound correspondingly behaves as a host material. As is known to those skilled in the art, host materials have higher singlet and triplet energies than the emitters, so that energy from the host material will also be transferred to the emitters with maximum efficiency. The systems disclosed in the prior art have exactly this energy relationship.
Preferred luminophores that can be used in combination with the compounds of the invention are described in particular in Sungho Nam et al, adv.sci.2021,2100586 and Eungdo Kin et al, sci.adv.2022,8,1641. Preferred triplet emitters or triplet emitter classes, also known as sensitizers in connection with super-fluorescent systems, are described in EP 3 435 A2, where emitters 2 and 3 on page 21 are preferred, in CN 109111487, where compounds indicated on pages 76 and 77 are preferred, in US2020/0140471, where compounds indicated on pages 166 to 175 are preferred, in KR 2020108705, where compounds indicated on pages 8 to 14 are preferred, in US 2019/01119112, where compounds indicated on pages 114 to 121 are preferred, and in US 2020/041775, where compounds indicated on pages 123 to 128 are preferred. Furthermore, preferred fluorescent emitters or classes of fluorescent emitters are described in WO 2021/090932, in which compounds indicated on pages 129 to 133, 157 to 166, 171 to 187, 200 to 211, 222 to 227, 236 to 252, 255 are preferred, in WO 2020/054676, in which compounds indicated on pages 44 to 104 are preferred, in WO 2020/017931, in which compounds indicated on pages 17 to 39 are preferred, in WO 2020/218079, in which compounds indicated on pages 64 to 258 are preferred, in WO 2018/212169, in which compounds indicated on pages 33 to 42 are preferred, in WO 2019/235452, in which compounds indicated on pages 46 to 168 are preferred, in US10,249,832, in which compounds indicated on pages 19 to 106 are preferred, and in WO 1/014001, in which compounds indicated on pages 107 to 129 are preferred.
It is also possible that other phosphorescent emitters which emit at wavelengths shorter than the wavelength of the actual emitter are present as co-hosts in the mixture. Particularly good results are achieved when the light emitter used is a red phosphorescent light emitter and the co-host used in combination with the compounds of the invention is a yellow phosphorescent light emitter.
Furthermore, the co-host used may be a compound that does not participate to a significant extent in charge transport even if it is, as described in, for example, WO 2010/108579. Especially suitable as co-matrix materials in combination with the compounds of the invention are compounds which have a large band gap and which do not participate, at least to a significant extent, in themselves even in the charge transport of the light-emitting layer. Such materials are preferably pure hydrocarbons. Examples of such materials can be found, for example, in WO 2009/124627 or in WO 2010/006680. In this case, it should be emphasized that the compounds of the invention have advantageous properties in the absence of specific functional groups, such as hole-transporting groups and/or electron-transporting groups.
Suitable phosphorescent compounds (=triplet emitters) are in particular compounds which emit light, preferably in the visible region, when suitably excited, and also contain at least one atom having an atomic number greater than 20, preferably greater than 38 and less than 84, more preferably greater than 56 and less than 80, in particular a metal having this atomic number. Phosphorescent emitters which are preferably used are compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, in particular compounds containing iridium or platinum.
Examples of such luminophores can be found in ：WO 00/70655、WO 2001/41512、WO 2002/02714、WO 2002/15645、EP 1191613、EP 1191612、EP 1191614、WO 05/033244、WO 05/019373、US2005/0258742、WO 2009/146770、WO 2010/015307、WO 2010/031485、WO 2010/054731、WO 2010/054728、WO 2010/086089、WO 2010/099852、WO 2010/102709、WO 2011/032626、WO 2011/066898、WO 2011/157339、WO 2012/007086、WO 2014/008982、WO 2014/023377、WO 2014/094961、WO 2014/094960、WO 2015/036074、WO 2015/104045、WO 2015/117718、WO 2016/015815、WO 2016/124304、WO 2017/032439 and WO 2018/01186 in the following applications. In general, all phosphorescent complexes for phosphorescent electroluminescent devices according to the prior art and known to the person skilled in the art of organic electroluminescence are suitable, and the person skilled in the art will be able to use other phosphorescent complexes without inventive effort.
Examples of phosphorescent dopants are listed in the following table:
The compounds of the invention are also particularly suitable as host materials for phosphorescent emitters in organic electroluminescent devices, as described for example in WO 98/24271, US 2011/024847 and US 2012/0223633. In these multicolor display assemblies, an additional blue light emitting layer is applied by vapor deposition over the entire area to all pixels, including pixels having a color other than blue.
In another embodiment of the invention the organic electroluminescent device of the invention does not contain any separate hole injection layer and/or hole transport layer and/or hole blocking layer and/or electron transport layer, meaning that the light emitting layer is directly adjacent to the hole injection layer or anode and/or the light emitting layer is directly adjacent to the electron transport layer or electron injection layer or cathode, as described for example in WO 2005/053051. In addition, the same or similar metal complexes as in the light-emitting layer can be used as hole-transporting or hole-injecting material directly adjoining the light-emitting layer, as described for example in WO 2009/030981.
In the other layers of the organic electroluminescent device of the present invention, any material commonly used according to the prior art may be used. Thus, the person skilled in the art will be able to use any material known for use in organic electroluminescent devices in combination with the compounds of the invention of formula (I) or the preferred embodiments described above, without the inventive effort.
Also preferred is an organic electroluminescent device, characterized in that one or more layers are applied by sublimation. In this case, the material is applied by vapor deposition in a vacuum sublimation system at an initial pressure of less than 10 -5 mbar, preferably less than 10 -6 mbar. However, the initial pressure may even be lower, for example less than 10 -7 mbar.
Also preferred is an organic electroluminescent device, characterized in that one or more layers are applied by the OVPD (organic vapor deposition) method or by means of carrier gas sublimation. In this case, the material is applied at a pressure of between 10 -5 mbar and 1 bar. One special case of this method is the OVJP (organic gas phase inkjet printing) method, in which the material is applied directly through a nozzle and is structured thereby.
Also preferred is an organic electroluminescent device characterized in that the layer or layers are produced from the solution, for example by spin coating, or by any printing method such as screen printing, flexography, offset printing, LITI (photoinitiated thermal imaging, thermal transfer), inkjet printing or nozzle printing. For this purpose, soluble compounds obtained, for example, by suitable substitution are required.
Formulations employing compounds of formula (I) or preferred embodiments thereof as detailed above are novel. The present invention therefore also provides a formulation comprising at least one solvent and a compound according to formula (I) or a preferred embodiment thereof as described in detail above.
Furthermore, a hybrid method is possible, for example, in which one or more layers are applied from solution and one or more other layers are applied by vapor deposition.
These methods are generally known to those skilled in the art and can be applied to organic electroluminescent devices comprising the compounds of the present invention without inventive effort.
The compounds according to the invention and the organic electroluminescent devices according to the invention are distinguished in particular by improved efficiency and/or operating voltage compared to the prior art. Furthermore, these compounds and the organic electroluminescent devices obtainable therefrom show improved lifetime. In a particular variant, the compounds according to the invention and the organic electroluminescent devices according to the invention are distinguished in particular by a low Refractive Index (RI) in comparison with the prior art. Furthermore, preferred compounds of the invention show a high triplet T1 level, so that these compounds are particularly suitable as host materials for triplet emitters for blue emission.
The electronic device, in particular the organic electroluminescent device, of the invention has one or more of the following surprising advantages over the prior art:
1. The compounds comprising the preferred embodiments of formula (I) or described in the context, in particular as matrix materials, as electron-conducting materials or as hole-conducting materials, have excellent efficiency in electronic devices, in particular organic electroluminescent devices. In this case, the compounds of the invention of formula (I) or the preferred embodiments described in the context bring about low operating voltages when used in electronic devices.
2. The compounds comprising the preferred embodiments of formula (I) or described in the context, in particular as matrix materials, as electron-conducting materials or as hole-conducting materials, in particular organic electroluminescent devices, have very good lifetimes. In this case, these compounds bring about, in particular, a low roll-off, i.e. a small decrease in the power efficiency of the device at high luminous densities.
3. The compounds of the invention of the preferred embodiments of formula (I) or the context indicated above show a very high stability and lifetime.
4. The compounds comprising the preferred embodiments of formula (I) or described in the context, in particular as matrix materials, as electron-conducting materials or as hole-conducting materials, in particular organic electroluminescent devices, have a high T1 energy level.
5. With the compounds of formula (I) or the preferred embodiments described above and below, the formation of optically lossy channels in electronic devices, especially organic electroluminescent devices, can be avoided. As a result, these devices are characterized by high PL efficiency of the light emitter and thus high EL efficiency, and excellent energy transfer from the host to the dopant.
6. The compounds of the preferred embodiments of formula (I) or the context described have excellent glass film formation.
7. The compounds of the preferred embodiments of formula (I) or the context indicated above form very good films from solution.
These above-mentioned advantages are not accompanied by a very serious deterioration of other electronic properties.
It should be noted that the scope of the invention covers variations of the embodiments described in the present invention. Any feature disclosed in this application may be interchanged with alternative features serving the same or equivalent or similar purpose, unless expressly excluded. Thus, unless otherwise indicated, any feature disclosed in this application is to be construed as an example of a generic series or equivalent or similar feature.
All of the features of the invention may be combined with each other in any way unless the specific features and/or steps are mutually exclusive. This is especially true of the preferred features of the invention. Also, features that are not necessarily combined may be used alone (rather than in combination).
It should also be noted that many features of the present invention, particularly those of the preferred embodiments, should be considered as inventive in themselves and not just as embodiments of the present invention. In addition to or instead of any of the presently claimed inventions, independent protection may be sought.
The technical teachings of the present disclosure may be refined and combined with other embodiments.
The present invention is illustrated in detail by the following examples, which are not intended to limit the invention in any way. Those skilled in the art will be able to practice the invention using the information given, without undue burden, to prepare and use other compounds of the invention in electronic devices, or to employ methods of the invention, throughout the scope of the disclosure.
Examples
Unless otherwise indicated, the following syntheses were carried out in dry solvents under a protective gas atmosphere. The metal complex needs to be additionally treated in the absence of light or yellow light. Solvents and reagents are available from, for example, sigma-ALDRICH or ABCR. The corresponding numbers in brackets or the numbers quoted for the individual compounds are associated with the CAS numbers for the compounds known from the literature. In the case of compounds which may have multiple enantiomeric, diastereomeric or tautomeric forms, one form is shown in a representative manner.
A) Preparation of synthon S
Example S1:
To 11.6g (100 mmol) of 2, 3-diamino-2, 3-dimethylbutane [20485-44-3], 9.9g (100 mmol) of 2, 3-tetramethylaziridine [5910-14-5] in 200ml of two To the mixture in the alkane was added dropwise 200ml of 1M bis HClThe alkane solution and then the mixture was stirred in a stirred autoclave at 110 ℃ for 8 hours. After cooling, most of the two are removed under reduced pressureThe residue was dissolved in 50ml of methanol, 300ml of 1N aqueous ammonia solution was added, the mixture was extracted five times with Dichloromethane (DCM), 100ml each time, the combined organic phases were dried over potassium carbonate, DCM was removed under reduced pressure, and the residue was fractionated under reduced pressure. Yield 5.1g (23 mmol), 23% purity about 97% according to 1 H-NMR.
Example S10:
a)S10a:
The procedure is similar to that of p.zhang et al, j.med.chem.,2009,52 (18), 5703.
A well-stirred mixture of 11.6g (100 mmol) of 2, 3-diamino-2, 3-dimethylbutane [20485-44-3], 7.1g (50 mmol) of 2-fluoronitrobenzene [1493-27-2] and 200ml of Dimethylformamide (DMF) was stirred at 30℃for 16 hours. Most of the DMF was removed under reduced pressure, the residue was dissolved in 300ml of Ethyl Acetate (EA), washed three times with 100ml of water each time, once with 100ml of saturated sodium chloride solution and dried over sodium sulfate. The drying agent was filtered off, the filtrate was concentrated to dryness, and the residue was chromatographed (Torrent automatic column system from a.semrau). Yield 8.8g (38 mmol), 76%, purity about 97% according to 1 H-NMR.
When 2-chloronitrobenzene is used, the reaction is carried out at 60℃to 80 ℃.
b)S10b
The procedure is similar to that of p.zhang et al, j.med.chem.,2009,52 (18), 5703.
A well stirred solution of 23.7g (100 mmol) of S10a in 200ml of methanol and 100ml of THF was hydrogenated over 5g of Pd/C at 5% by weight at 30℃at about 4 bar until the hydrogen uptake ceased (about 8 hours). The catalyst was filtered off as a THF slurry using a celite bed and the filtrate was concentrated to dryness. Yield 20.6g (100 mmol), quantitative and purity about 97% according to 1 H-NMR.
The nitro function can alternatively be reduced with tin or zinc in an aqueous hydrochloric acid medium.
c)S10:
The process is similar to that of M.T.Blzquez et al, heterycles, 2006,69,73 and WO 2012130709. To a well-stirred solution of 20.7g (100 mmol) of S1b cooled to 0℃in 500ml of DCM was added dropwise 50ml (100 mmol) of phosgene, 20% by weight toluene solution. The reaction mixture was allowed to warm gradually to room temperature and heated to reflux for 12 hours (note: evolution of HCl. Subsequently, the solvent was distilled off completely, 100g of polyphosphoric acid was added, the mixture was heated to 100 ℃ and homogenized by stirring (precision glass tower), and the reaction mixture was heated to 220 ℃ while stirring for 1 hour. The mixture was stirred for 3 hours at 220℃and allowed to cool to 80℃and then 500ml of water were gradually added (note: exotherm. After cooling, the solid was filtered off with suction, washed three times with 100ml each time, once with 50ml of methanol, and dried with suction. The solid was suspended in 150ml of methanol, 50ml of concentrated aqueous ammonia was added, the mixture was stirred for 30 minutes, the solid was filtered off with suction, washed twice with 30ml of methanol each time, and dried under reduced pressure. Yield 17.5g (80 mmol), 80% purity about 97% according to 1 H-NMR.
The following compounds may be prepared analogously:
B) Synthesis examples B1a and B1B of the compounds of the invention:
Variant 1 Ullman coupling
The process is similar to WO 2012/130709. A well stirred mixture of 21.5g (100 mmol) of S10, 24.5g (120 mmol) of iodobenzene [591-50-4], 65.2g (200 mmol) of cesium carbonate, 3.8g (20 mmol) of cuprous (I) iodide, 4.6g (40 mmol) of L-proline, 100g of glass beads (diameter 3 mm) and 500ml of dimethyl sulfoxide (DMSO) was stirred at 100℃for 16 hours (using aryl/heteroaryl bromide at 130℃to 160℃or in N-methyl-2-pyrrolidone at 200 ℃). The mixture was filtered through a bed of celite as a slurry of DMSO while still warm, the filtrate was poured into 2000ml of water while stirring, the precipitated solid was filtered, washed three times with 100ml each time, twice with 100ml each time with ethanol, and dried under reduced pressure. The solid was dissolved in dichloromethane and filtered through a silica gel bed as a slurry of DCM, and the filtrate was gradually concentrated on a rotary evaporator, continuing to replace distilled DCM with ethanol. The crystalline product is filtered off with suction, washed twice with 50ml of ethanol and dried under reduced pressure. Further separation of the isomers B1a and B1B and their purification is carried out by chromatographic separation (Torrent automatic column system from Semrau), by repeated thermal extraction crystallization (conventional organic solvents or combinations thereof, preferably acetonitrile-DCM, 1:3 to 3:1, volume: volume) and by fractional sublimation or heat treatment under high vacuum.
Yield:
B1a:15.7g (53 mmol), 53%, purity: about 99.9%, according to HPLC.
B1.1 g (17 mmol), 17%, purity about 99.9% according to HPLC.
Variant 2 Ullman coupling
24Ml (200 mmol) of trans-1, 2-diaminocyclohexane can be used instead of L-proline, with the use of twoAlkane replaces DMSO.
Yield:
B1a:16.7g (57 mmol), 57%, purity about 99.9% according to HPLC.
B1B 4.5g (15 mmol), 15%, purity about 99.9% according to HPLC.
Examples B2a and B2B:
variant 3:S N Ar reaction
The process is similar to WO 2012/130709. A well-stirred mixture of 21.5g (100 mmol) of S10, 14.5g (120 mmol) of 4-fluorobenzonitrile [1194-02-1], 41.5g (300 mmol) of potassium carbonate, 100g of glass beads (diameter 3 mm) and 500ml of dimethylacetamide (DMAc) was stirred at 160℃for 16 hours. The mixture was filtered through a celite bed in the form of a DMAc slurry while still warm, the filtrate was poured into 2000ml of water with stirring, the precipitated solid was filtered, washed three times with 100ml of water, twice with 100ml of ethanol, 100ml of ethanol and dried under reduced pressure. The solid was dissolved in dichloromethane and filtered through a silica gel bed as a slurry of DCM, and the filtrate was gradually concentrated on a rotary evaporator, continuing to replace distilled DCM with ethanol. The crystalline product is filtered off with suction, washed twice with 50ml of ethanol and dried under reduced pressure. Further purification is as described in B1 a/B1B.
Yield:
B2a:14.7g (47 mmol), 47%, purity about 99.9% according to HPLC.
B2b-4.4 g (14 mmol),%; purity: about 99.9%, according to HPLC.
Examples B200a and B200B:
variant 4:S N Ar reaction
To a solution of 22.6g (105 mmol) of S10 in 300ml of DMF was added in portions 2.4g (100 mmol) of sodium hydride (note: evolution of hydrogen. Subsequently, 37.8g (110 mmol) of 2- [1,1' -biphenyl ] -4-yl-4-chloro-6-phenyl-1, 3, 5-triazine [1472062-94-4] was added and the mixture was stirred at room temperature for 5 hours. 2000ml of water were added dropwise while stirring, the precipitated solid was filtered, washed three times with 100ml of water each time, twice with 100ml of ethanol each time, and dried under reduced pressure. The solid was dissolved in dichloromethane and filtered through a silica gel bed as a slurry of DCM, and the filtrate was gradually concentrated on a rotary evaporator, continuing to replace distilled DCM with ethanol. The crystalline product is filtered off with suction, washed twice with 50ml of ethanol and dried under reduced pressure. Further purification was as described in B1.
Yield:
B200a:31.2g (60 mmol), 60%, purity: about 99.9% according to HPLC.
B200B 6.2g (12 mmol), 12%, purity about 99.9% according to HPLC.
The following compounds can be prepared analogously, wherein the stoichiometry is adjusted to the corresponding number of bonds to be formed.
Example fabrication of OLED
1) Vacuum-treated devices:
The OLEDs of the invention and the OLEDs according to the prior art are manufactured by the general method according to WO 2004/058911, which is adapted to the environment described herein (layer thickness, variation of the materials used).
In the examples that follow, the results of a variety of OLEDs are presented. Clean glass plates (cleaned in a Miele laboratory glass washer, merck Extran detergent) coated with 50nm thick structured ITO (indium tin oxide) were pre-treated with UV ozone for 25 minutes (UVP PR-100UV ozone generator). These coated glass sheets form the substrate to which the OLED is applied.
1A) Blue fluorescent OLED assembly-BF:
The compounds of the present invention may be used in a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Transport Layer (ETL). All materials were applied by thermal vapor deposition in a vacuum chamber. The light-emitting layer (EML) here always consists of at least one host material (host material) SMB (see table 1) and a light-emitting dopant (dopant, emitter) D, which is added to the host material or materials in a specific volume ratio by co-evaporation. Detailed information given in the form of, for example, SMB: D (97:3%) means here that the material SMB is present in the layer in a proportion of 97% by volume and the dopant D is present in the layer in a proportion of 3% by volume. Similarly, the electron transport layer may also be composed of a mixture of two materials, see Table 1. The materials used to produce the OLEDs are shown in table 5 or are associated with the synthesis examples detailed above.
The OLED was characterized in a standard manner. For this purpose, an electroluminescence spectrum was determined, current efficiency (measured in cd/a), power efficiency (measured in lm/W) and external quantum efficiency (EQE measured in%) as a function of emission density were calculated from current-voltage-emission density characteristics (IUL characteristics) assuming Lambertian emission characteristics, and lifetime was also measured. EQE in (%) and voltage in (V) are reported at an emission density of 1000cd/m 2.
The OLED has the following layer structure:
Substrate
Hole Injection Layer (HIL) consisting of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20nm
Hole Transport Layer (HTL), see Table 1
Electron Blocking Layer (EBL), see table 1
Luminescent layer (EML), see Table 1
Electron Transport Layer (ETL), see table 1
Electron Injection Layer (EIL) composed of ETM2, 1nm
Cathode composed of aluminum, 100nm
TABLE 1 Structure of blue fluorescent OLED Assembly
TABLE 2 results for blue fluorescent OLED assemblies
Examples EQE(%) Voltage (V)
BF1 8.6 3.8
BF2 8.0 3.9
BF3 8.3 3.8
BF4 8.7 3.7
BF5 8.3 3.8
1B) Phosphorescent OLED assembly:
The compound a of the present invention may be used in a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), and as a host material (host material) M (see table 5) or a (see the material of the present invention) in an emission layer (EML). For this purpose, all materials are applied by thermal vapor deposition in a vacuum chamber. The light-emitting layer here always consists of at least one or more matrix materials M and phosphorescent dopants Ir which are added to the matrix material or materials in a specific volume ratio by co-evaporation. Detailed information given in the form of, for example, m1:m2:ir (55%: 35%: 10%) means here that the material M1 is present in the layer in a proportion of 55% by volume, M2 is present in the layer in a proportion of 35% by volume, and Ir is present in the layer in a proportion of 10% by volume. Similarly, the electron transport layer may also be composed of a mixture of two materials. The exact structure of the OLED can be found in table 3. The materials used to produce the OLEDs are shown in table 5 or are associated with the synthesis examples detailed above.
The OLED was characterized in a standard manner. For this purpose, an electroluminescence spectrum was determined, current efficiency (measured in cd/a), power efficiency (measured in lm/W) and external quantum efficiency (EQE measured in%) as a function of luminescence density were calculated from current-voltage-luminescence density characteristics (IUL characteristics) assuming lambertian luminescence characteristics, and lifetime was also measured. EQE in (%) and voltage in (V) are reported at an emission density of 1000cd/m 2.
The OLED has the following layer structure:
Substrate
Hole Injection Layer (HIL) consisting of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20nm
Hole Transport Layer (HTL), see Table 3
Electron Blocking Layer (EBL), see table 3
Luminescent layer (EML), see Table 3
Hole Blocking Layer (HBL), see Table 3
An Electron Transport Layer (ETL) composed of ETM1:ETM2 (50%: 50%) at 30nm
Electron Injection Layer (EIL) composed of ETM2, 1nm
Cathode composed of aluminum, 100nm
TABLE 3 Structure of phosphorescent OLED Assembly
TABLE 4 results for phosphorescent OLED assemblies
TABLE 5 structural formula of the materials used

Claims (17)

1.一种化合物，所述化合物包含至少一个式(I)的结构，1. A compound comprising at least one structure of formula (I), 其中符号如下：The symbols are as follows: Z在每种情况下相同或不同并且为Ar或R；Z is identical or different in each case and is Ar or R; W1在每种情况下相同或不同并且为-C(Ra)2-(Y)n-C(Rb)2-基团、为-C(Rc)＝C(Rc)-基团或者为邻位连接的芳族或杂芳族环系，所述芳族或杂芳族环系具有5至60个芳族环原子并且可被一个或多个Rd基团取代；W 1 is identical or different in each case and is a —C(R a ) 2 —(Y) n —C(R b ) 2 — group, a —C(R c )═C(R c )— group or an ortho-attached aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and which may be substituted by one or more R d groups; W2在每种情况下相同或不同并且为-C(Ra)2-(Y)n-C(Rb)2-基团、为-C(Rc)＝C(Rc)-基团或者为邻位连接的芳族或杂芳族环系，所述芳族或杂芳族环系具有5至60个芳族环原子并且可被一个或多个Rd基团取代；W 2 is identical or different in each case and is a —C(R a ) 2 —(Y) n —C(R b ) 2 — group, a —C(R c )═C(R c )— group or an ortho-attached aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more R d groups; R在每种情况下相同或不同并且为H，D，OH，F，Cl，Br，I，CN，NO2，N(Ar)2，N(Re)2，C(＝O)N(Ar)2，C(＝O)N(Re)2，C(Ar)3，C(Re)3，Si(Ar)3，Si(Re)3，B(Ar)2，B(Re)2，C(＝O)Ar，C(＝O)Re，P(＝O)(Ar)2，P(＝O)(Re)2，P(Ar)2，P(Re)2，S(＝O)Ar，S(＝O)Re，S(＝O)2Ar，S(＝O)2Re，OSO2Ar，OSO2Re，具有1至40个碳原子的直链的烷基、烷氧基或硫代烷氧基基团或者具有2至40个碳原子的烯基或炔基基团或者具有3至20个碳原子的支链或环状的烷基、烷氧基或硫代烷氧基基团，其中所述烷基、烷氧基、硫代烷氧基、烯基或炔基基团在每种情况下可被一个或多个Re基团取代，其中一个或多个不相邻的CH2基团可被ReC＝CRe、C≡C、Si(Re)2、C＝O、C＝S、C＝Se、C＝NRe、-C(＝O)O-、-C(＝O)NRe-、NRe、P(＝O)(Re)、-O-、-S-、SO或SO2代替，或者具有5至60个芳族环原子并且在每种情况下可被一个或多个Re基团取代的芳族或杂芳族环系，或者具有5至60个芳族环原子和在烷基基团中的1至10个碳原子并且可被一个或多个Re基团取代的芳烷基或杂芳烷基基团；同时，R基团可与其它基团形成环系；R is in each case identical or different and is H, D, OH, F, Cl, Br, I, CN, NO2 , N(Ar) 2 , N( Re ) 2 , C(=O)N(Ar) 2 , C(=O)N( Re ) 2 , C(Ar) 3 , C(Re ) 3 , Si(Ar) 3 , Si( Re ) 3 , B( Ar ) 2 , B(Re) 2 , C(=O)Ar, C(=O) Re , P(=O)(Ar ) 2 , P(=O)(Re) 2 , P(Ar) 2 , P( Re ) 2 , S(=O) Ar , S(=O) Re , S(=O) 2Ar , S(= O ) 2Re , OSO2Ar , OSO2Re , a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, wherein the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may in each case be substituted by one or more Re groups, wherein one or more non-adjacent CH 2 groups may be replaced by Re C═CR e , C≡C, Si( Re ) 2 , C═O, C═S, C═Se, C═NR e , —C(═O)O—, —C(═O)NR e —, NRe , P(═O)( Re ), —O—, —S—, SO or SO 2 , or having 5 to 60 aromatic ring atoms and in each case being substituted by one or more R an aromatic or heteroaromatic ring system substituted with an R e group, or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms and 1 to 10 carbon atoms in the alkyl group and which may be substituted with one or more R e groups; at the same time, the R group may form a ring system with other groups; Ar在每种情况下相同或不同并且为具有5至60个芳族环原子并且可被一个或多个Re基团取代的芳族或杂芳族环系；同时，与同一碳原子、硅原子、氮原子、磷原子或硼原子键合的两个Ar基团也可通过单键或者选自B(Re)、C(Re)2、Si(Re)2、C＝O、C＝NRe、C＝C(Re)2、O、S、S＝O、SO2、N(Re)、P(Re)和P(＝O)Re的桥连基桥连在一起；Ar is in each case identical or different and is an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and which may be substituted by one or more Re groups; at the same time, two Ar groups bonded to the same carbon, silicon, nitrogen, phosphorus or boron atom may also be bridged together via a single bond or a bridging group selected from B( Re ), C( Re ) 2 , Si( Re ) 2 , C=O, C= NRe , C=C( Re ) 2 , O, S, S=O, SO2 , N( Re ), P( Re ) and P(=O) Re ; Ra、Rb在每种情况下相同或不同并且为OH，F，Cl，Br，I，CN，NO2，N(Ar')2，N(R1)2，C(＝O)N(Ar')2，C(＝O)N(R1)2，C(Ar')3，C(R1)3，Si(Ar')3，Si(R1)3，B(Ar')2，B(R1)2，C(＝O)Ar'，C(＝O)R1，P(＝O)(Ar')2，P(＝O)(R1)2，P(Ar')2，P(R1)2，S(＝O)Ar'，S(＝O)R1，S(＝O)2Ar'，S(＝O)2R1，OSO2Ar'，OSO2R1，具有1至40个碳原子的直链的烷基、烷氧基或硫代烷氧基基团或者具有2至40个碳原子的烯基或炔基基团或者具有3至20个碳原子的支链或环状的烷基、烷氧基或硫代烷氧基基团，其中所述烷基、烷氧基、硫代烷氧基、烯基或炔基基团在每种情况下可被一个或多个R1基团取代，其中一个或多个不相邻的CH2基团可被R1C＝CR1、C≡C、Si(R1)2、C＝O、C＝S、C＝Se、C＝NR1、-C(＝O)O-、-C(＝O)NR1-、NR1、P(＝O)(R1)、-O-、-S-、SO或SO2代替，或者具有5至60个芳族环原子并且在每种情况下可被一个或多个R1基团取代的芳族或杂芳族环系，或者具有5至60个芳族环原子并且可被一个或多个R1基团取代的芳氧基或杂芳氧基基团；同时，两个Ra、Rb基团也可彼此形成环系或与其它基团形成环系；R a , R b are in each case identical or different and are OH, F, Cl, Br, I, CN, NO 2 , N(Ar′) 2 , N(R 1 ) 2 , C(═O)N(Ar′) 2 , C(═O)N(R 1 ) 2 , C(Ar′) 3 , C(R 1 ) 3 , Si(Ar′) 3 , Si(R 1 ) 3 , B(Ar′) 2 , B(R 1 ) 2 , C(═O)Ar′, C(═O)R 1 , P(═O)(Ar′) 2 , P(═O)(R 1 ) 2 , P(Ar′) 2 , P(R 1 ) 2 , S(═O)Ar′, S(═O)R 1 , S(═O) 2 Ar′, S(═O) 2 R 1 , OSO 2 Ar', OSO 2 R 1 , a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, wherein the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may in each case be substituted by one or more R 1 groups, wherein one or more non-adjacent CH 2 groups may be replaced by R 1 C═CR 1 , C≡C, Si(R 1 ) 2 , C═O, C═S, C═Se, C═NR 1 , —C(═O)O—, —C(═O)NR 1 — , NR 1 , P(═O)(R 1 ), —O—, —S—, SO or SO 2 , or a cycloalkyl group having 5 to 60 aromatic ring atoms and in each case being substituted by one or more R an aromatic or heteroaromatic ring system substituted with a R 1 group, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms and which may be substituted with one or more R 1 groups; at the same time, the two R a and R b groups may also form a ring system with each other or with other groups; n为0或1，其中，当n＝0时，Y基团不存在，并且两个-C(Ra)2-和-C(Rb)2-基团彼此直接键合；n is 0 or 1, wherein, when n=0, the Y group is absent, and the two -C(R a ) 2 - and -C(R b ) 2 - groups are directly bonded to each other; Y在每种情况下相同或不同并且为C(Rc)2、C(Rc)2-C(Rc)2、C(Rc)＝C(Rc)；Y is identical or different at each occurrence and is C(R c ) 2 , C(R c ) 2 —C(R c ) 2 , or C(R c )═C(R c ); Rc、Rd、Re在每种情况下相同或不同并且为H，D，OH，F，Cl，Br，I，CN，NO2，N(Ar')2，N(R1)2，C(＝O)N(Ar')2，C(＝O)N(R1)2，C(Ar')3，C(R1)3，Si(Ar')3，Si(R1)3，Ge(Ar')3，Ge(R1)3，B(Ar')2，B(R1)2，C(＝O)Ar'，C(＝O)R1，P(＝O)(Ar')2，P(＝O)(R1)2，P(Ar')2，P(R1)2，S(＝O)Ar'，S(＝O)R1，S(＝O)2Ar'，S(＝O)2R1，OSO2Ar'，OSO2R1，具有1至40个碳原子的直链的烷基、烷氧基或硫代烷氧基基团或者具有2至40个碳原子的烯基或炔基基团或者具有3至20个碳原子的支链或环状的烷基、烷氧基或硫代烷氧基基团，其中所述烷基、烷氧基、硫代烷氧基、烯基或炔基基团在每种情况下可被一个或多个R1基团取代，其中一个或多个不相邻的CH2基团可被R1C＝CR1、C≡C、Si(R1)2、Ge(R1)2、C＝O、C＝S、C＝Se、C＝NR1、-C(＝O)O-、-C(＝O)NR1-、NR1、P(＝O)(R1)、-O-、-S-、SO或SO2代替，或者具有5至60个芳族环原子并且在每种情况下可被一个或多个R1基团取代的芳族或杂芳族环系，或者具有5至60个芳族环原子并且可被一个或多个R1基团取代的芳氧基或杂芳氧基基团；同时，两个Rc、Rd、Re基团也可彼此形成环系或与其它基团形成环系；R c , R d , and Re are in each case identical or different and are H, D, OH, F, Cl, Br, I, CN, NO 2 , N(Ar′) 2 , N(R 1 ) 2 , C(═O)N(Ar′) 2 , C(═O)N(R 1 ) 2 , C(Ar′) 3 , C(R 1 ) 3 , Si(Ar′) 3 , Si(R 1 ) 3 , Ge(Ar′) 3 , Ge(R 1 ) 3 , B(Ar′) 2 , B(R 1 ) 2 , C(═O)Ar′, C(═O)R 1 , P(═O)(Ar′) 2 , P(═O)(R 1 ) 2 , P(Ar′) 2 , P(R 1 ) 2 , S(═O)Ar′, S(═O)R 1 , S(═O) 2 Ar′, S(═O) 2 R 1 , OSO 2 Ar′, OSO 2 R 1 , a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, or an alkenyl or alkynyl group having 2 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, wherein the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may in each case be substituted by one or more R 1 groups, wherein one or more non-adjacent CH 2 groups may be replaced by R 1 C═CR 1 , C≡C, Si(R 1 ) 2 , Ge(R 1 ) 2 , C═O, C═S, C═Se, C═NR 1 , —C(═O)O—, —C(═O)NR 1 —, NR 1 , P(═O)(R 1 ), —O—, —S—, SO or SO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and which may in each case be substituted by one or more R 1 groups, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms and which may be substituted by one or more R 1 groups; at the same time, two R c , R d , and Re groups may also form a ring system with each other or with other groups; Ar'在每种情况下相同或不同并且为具有5至60个芳族环原子并且可被一个或多个R1基团取代的芳族或杂芳族环系，其中与同一碳原子、硅原子、氮原子、磷原子或硼原子键合的两个Ar'基团也可通过单键或者选自B(R1)、C(R1)2、Si(R1)2、C＝O、C＝NR1、C＝C(R1)2、O、S、S＝O、SO2、N(R1)、P(R1)和P(＝O)R1的桥连基彼此桥连；Ar′ is in each case identical or different and is an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and which may be substituted by one or more R 1 groups, where two Ar′ groups bonded to the same carbon, silicon, nitrogen, phosphorus or boron atom may also be bridged to one another via a single bond or a bridging group selected from the group consisting of B(R 1 ), C(R 1 ) 2 , Si(R 1 ) 2 , C═O, C═NR 1 , C═C(R 1 ) 2 , O, S, S═O, SO 2 , N(R 1 ), P(R 1 ) and P(═O)R 1 ; R1在每种情况下相同或不同并且为H，D，F，Cl，Br，I，CN，NO2，N(Ar”)2，N(R2)2，C(＝O)Ar”，C(＝O)R2，P(＝O)(Ar”)2，P(Ar”)2，B(Ar”)2，B(R2)2，C(Ar”)3，C(R2)3，Si(Ar”)3，Si(R2)3，Ge(Ar”)3，Ge(R2)3，具有1至40个碳原子的直链的烷基、烷氧基或硫代烷氧基基团或者具有3至40个碳原子的支链或环状的烷基、烷氧基或硫代烷氧基基团或者具有2至40个碳原子的烯基基团，所述基团各自可被一个或多个R2基团取代，其中一个或多个不相邻的CH2基团可被-R2C＝CR2-、-C≡C-、Si(R2)2、Ge(R2)2、C＝O、C＝S、C＝Se、C＝NR2、-C(＝O)O-、-C(＝O)NR2-、NR2、P(＝O)(R2)、-O-、-S-、SO或SO2代替并且其中一个或多个氢原子可被D、F、Cl、Br、I、CN或NO2代替，或者具有5至60个芳族环原子并且在每种情况下可被一个或多个R2基团取代的芳族或杂芳族环系，或者具有5至60个芳族环原子并且可被一个或多个R2基团取代的芳氧基或杂芳氧基基团，或者具有5至60个芳族环原子并且可被一个或多个R2基团取代的芳烷基或杂芳烷基基团，或者这些体系的组合；同时，两个或更多个R1基团可彼此形成环系；同时，一个或多个R1基团可与所述化合物的另外的部分形成环系； R1 is identical or different in each case and is H, D, F, Cl, Br, I, CN, NO2 , N(Ar") 2 , N( R2 ) 2 , C(=O)Ar", C(=O) R2 , P(=O)(Ar") 2 , P(Ar") 2 , B(Ar") 2 , B( R2 ) 2 , C(Ar") 3 , C( R2 ) 3 , Si(Ar") 3 , Si( R2 ) 3 , Ge(Ar") 3 , Ge( R2 ) 3 , a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or an alkenyl group having 2 to 40 carbon atoms, each of which may be replaced by one or more R 2 groups, in which one or more non-adjacent CH 2 groups can be replaced by -R 2 C═CR 2 -, -C≡C-, Si(R 2 ) 2 , Ge(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , -C(═O)O-, -C(═O)NR 2 -, NR 2 , P(═O)(R 2 ), -O-, -S-, SO or SO 2 and in which one or more hydrogen atoms can be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and which can in each case be substituted by one or more R 2 groups, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms and which can be substituted by one or more R 2 groups, or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms and which can be substituted by one or more R 2 groups, or a combination of these systems; at the same time, two or more R 1 groups may form a ring system with each other; at the same time, one or more R 1 groups may form a ring system with another part of the compound; Ar”在每种情况下相同或不同并且为具有5至30个芳族环原子并且可被一个或多个R2基团取代的芳族或杂芳族环系，其中与同一碳原子、硅原子、氮原子、磷原子或硼原子键合的两个Ar”基团也可通过单键或者选自B(R2)、C(R2)2、Si(R2)2、C＝O、C＝NR2、C＝C(R2)2、O、S、S＝O、SO2、N(R2)、P(R2)和P(＝O)R2的桥连基彼此桥连；Ar″ are in each case identical or different and are an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms and which may be substituted by one or more R 2 radicals, where two Ar″ radicals which are bonded to the same carbon, silicon, nitrogen, phosphorus or boron atom may also be bridged to one another via a single bond or a bridging group selected from the group consisting of B(R 2 ), C(R 2 ) 2 , Si(R 2 ) 2 , C═O, C═NR 2 , C═C(R 2 ) 2 , O, S, S═O, SO 2 , N(R 2 ), P(R 2 ) and P(═O)R 2 ; R2在每种情况下相同或不同并且选自H，D，F，CN，具有1至20个碳原子的脂族烃基基团或者具有5至30个芳族环原子并且其中一个或多个氢原子可被D、F、Cl、Br、I或CN代替的芳族或杂芳族环系，并且所述芳族或杂芳族环系可被一个或多个各自具有1至4个碳原子的烷基基团取代；同时，两个或更多个取代基R2一起可形成环系；R 2 is identical or different in each case and is selected from H, D, F, CN, an aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms and in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN, and the aromatic or heteroaromatic ring system may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; at the same time, two or more substituents R 2 together may form a ring system; 其特征在于，W1、W2基团中的至少一个为-C(Ra)2-(Y)n-C(Rb)2-基团。It is characterized in that at least one of the W 1 and W 2 groups is a -C(R a ) 2 -(Y) n -C(R b ) 2 - group. 2.根据权利要求1所述的化合物，所述化合物包含至少一个式(I-1)至(I-18)的结构，2. The compound according to claim 1, comprising at least one structure of formula (I-1) to (I-18), 其中符号Z、Ra、Rb和Rc具有权利要求1中给出的定义，V为B(Rd)、C(Rd)2、Si(Rd)2、N(Rd)、O、S，并且X为N或C(Rd)。wherein the symbols Z, Ra , Rb and Rc have the definitions given in claim 1, V is B( Rd ), C( Rd ) 2 , Si( Rd ) 2 , N( Rd ), O, S, and X is N or C( Rd ). 3.根据权利要求1或2所述的化合物，其特征在于Ar或R基团为具有5至13个芳族环原子并且可被一个或多个Re基团取代的芳族或杂芳族环系。3. Compound according to claim 1 or 2, characterized in that the Ar or R group is an aromatic or heteroaromatic ring system having 5 to 13 aromatic ring atoms and which may be substituted by one or more Re groups. 4.根据权利要求1至3中的一项或多项所述的化合物，所述化合物包含至少一个式(II-1)至(II-8)的结构，4. Compounds according to one or more of claims 1 to 3, comprising at least one structure of formula (II-1) to (II-8), 其中符号Ra、Rb、Rc和Rd具有权利要求1中给出的定义，并且使用的其它符号如下：wherein the symbols Ra , Rb , Rc and Rd have the definitions given in claim 1, and the other symbols used are as follows: Ye在每种情况下相同或不同并且为B(Re)、C(Re)2、Si(Re)2、Ge(Re)2、C＝O、C＝NRe、C＝C(Re)2、O、S、S＝O、SO2、N(Re)、P(Re)或P(＝O)Re，其中Re具有权利要求1中给出的定义，或者如果有基团与所述结构键合，则Ye为B、C(Re)-、Si(Re)-；Y e is in each case identical or different and is B(R e ), C(R e ) 2 , Si(R e ) 2 , Ge(R e ) 2 , C═O, C═NR e , C═C(R e ) 2 , O, S, S═O, SO 2 , N(R e ), P(R e ) or P(═O)R e , where R e has the definition given in claim 1 , or, if there are groups bonded to the structure, Y e is B, C(R e )—, Si(R e )—; Xe在每种情况下相同或不同并且为N、CRe，或如果有基团与所述结构键合则Xe为C，条件是环中不多于三个的Xe基团为N，其中Re具有权利要求1中给出的定义； Xe is identical or different in each case and is N, CRe , or, if any groups are bonded to the structure , C, with the proviso that not more than three Xe groups in the ring are N, wherein Re has the meaning given in claim 1; m为0、1、2、3或4。m is 0, 1, 2, 3 or 4. 5.根据权利要求1至4中的一项或多项所述的化合物，所述化合物包含至少一个式(III-1)至(III-32)的结构，5. Compounds according to one or more of claims 1 to 4, comprising at least one structure of formula (III-1) to (III-32), 其中符号Ra、Rb、Rc、Rd和Re具有权利要求1中给出的定义，并且使用的其它符号如下：wherein the symbols Ra , Rb , Rc , Rd and Re have the definitions given in claim 1, and other symbols used are as follows: Ye在每种情况下相同或不同并且为B(Re)、C(Re)2、Si(Re)2、Ge(Re)2、C＝O、C＝NRe、C＝C(Re)2、O、S、S＝O、SO2、N(Re)、P(Re)或P(＝O)Re；Y e is in each case identical or different and is B(R e ), C(R e ) 2 , Si(R e ) 2 , Ge(R e ) 2 , C═O, C═NR e , C═C(R e ) 2 , O, S, S═O, SO 2 , N(R e ), P(R e ) or P(═O)R e ; j为0、1或2；j is 0, 1, or 2; n为0、1、2或3；n is 0, 1, 2, or 3; m为0、1、2、3或4；m is 0, 1, 2, 3 or 4; l为0、1、2、3、4或5。l is 0, 1, 2, 3, 4 or 5. 6.根据权利要求1至5中的一项或多项所述的化合物，其特征在于至少一个Rc、Rd、Re基团在每种情况下相同或不同并且选自H，D，具有3至20个碳原子的支链或环状的烷基、烷氧基或硫代烷氧基基团或者选自下式Ar-1至Ar-76的基团的芳族或杂芳族环系，或者Rc、Rd、Re基团在每种情况下相同或不同并且选自H，D或者选自下式Ar-1至Ar-76的基团的芳族或杂芳族环系，和/或Ar'基团在每种情况下相同或不同并且选自下式Ar-1至Ar-76的基团：6. Compounds according to one or more of claims 1 to 5, characterized in that at least one R c , R d , Re radical is in each case identical or different and is selected from H, D, a branched or cyclic alkyl, alkoxy or thioalkoxy radical having 3 to 20 carbon atoms or an aromatic or heteroaromatic ring system selected from the group consisting of the following formulae Ar-1 to Ar-76, or R c , R d , Re radical is in each case identical or different and is selected from H, D or an aromatic or heteroaromatic ring system selected from the group consisting of the following formulae Ar-1 to Ar-76, and/or Ar′ radicals are in each case identical or different and are selected from the group consisting of the following formulae Ar-1 to Ar-76: 其中R1具有上面给出的定义，虚线键表示与相应的基团连接的键，此外：wherein R 1 has the definition given above, the dotted bond represents the bond to the corresponding radical, and in addition: Ar1在每种情况下相同或不同并且为具有6至18个芳族环原子并且在每种情况下可被一个或多个R1基团取代的二价芳族或杂芳族环系；Ar 1 is identical or different in each case and is a divalent aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms and which may be substituted in each case by one or more R 1 groups; A在每种情况下相同或不同并且为C(R1)2、NR1、O或S；A is identical or different in each occurrence and is C(R 1 ) 2 , NR 1 , O or S; p为0或1，其中p＝0是指Ar1基团不存在，并且相应的芳族或杂芳族基团直接与相应的基团键合；p is 0 or 1, wherein p=0 means that the Ar 1 group is absent and the corresponding aromatic or heteroaromatic group is directly bonded to the corresponding group; q为0或1，其中q＝0是指没有A基团键合在该位置，而R1基团与相应的碳原子键合。q is 0 or 1, wherein q=0 means that no A group is bonded to that position, and the R 1 group is bonded to the corresponding carbon atom. 7.根据前述权利要求中的至少一项所述的化合物，其特征在于与一个碳原子键合的Ra基团选自具有1至10个碳原子的直链的烷基基团或者具有3至10个碳原子的支链或环状的烷基基团，所述基团各自可被一个或多个R1基团取代，其中两个或更多个取代基Ra一起可形成环系。7. Compound according to at least one of the preceding claims, characterized in that the Ra group bonded to one carbon atom is selected from linear alkyl groups having 1 to 10 carbon atoms or branched or cyclic alkyl groups having 3 to 10 carbon atoms, each of which may be substituted by one or more R groups, wherein two or more substituents Ra together can form a ring system. 8.根据前述权利要求中的至少一项所述的化合物，其特征在于与一个碳原子键合的Rb基团选自具有1至10个碳原子的直链的烷基基团或者具有3至10个碳原子的支链或环状的烷基基团，所述基团各自可被一个或多个R1基团取代，其中两个或更多个取代基Ra一起可形成环系。8. Compound according to at least one of the preceding claims, characterized in that the R group bonded to one carbon atom is selected from linear alkyl groups having 1 to 10 carbon atoms or branched or cyclic alkyl groups having 3 to 10 carbon atoms, each of which may be substituted by one or more R groups, wherein two or more substituents R together can form a ring system. 9.根据前述权利要求中的至少一项所述的化合物，其特征在于所述化合物包含至少一个电子传输基团和/或吸电子基团。9 . The compound according to claim 1 , wherein the compound comprises at least one electron-transporting and/or electron-withdrawing group. 10.根据前述权利要求中的至少一项所述的化合物，其特征在于所述化合物包含至少一个空穴传输基团。10 . The compound according to claim 1 , wherein the compound comprises at least one hole-transporting group. 11.一种低聚物、聚合物或树枝状大分子，所述低聚物、聚合物或树枝状大分子含有一种或多种根据权利要求1至10中的任一项所述的化合物，其中，存在所述化合物的一个或多个与所述聚合物、低聚物或树枝状大分子连接的键来代替氢原子或取代基。11. An oligomer, polymer or dendrimer comprising one or more compounds according to any one of claims 1 to 10, wherein one or more bonds of said compound to said polymer, oligomer or dendrimer are present instead of a hydrogen atom or a substituent. 12.一种制剂，所述制剂包含至少一种根据权利要求1至10中的一项或多项所述的化合物或者根据权利要求11所述的低聚物、聚合物或树枝状大分子以及至少一种其它化合物，其中所述其它化合物选自一种或多种溶剂。12. A preparation comprising at least one compound according to one or more of claims 1 to 10 or an oligomer, polymer or dendrimer according to claim 11 and at least one further compound, wherein the further compound is selected from one or more solvents. 13.一种组合物，所述组合物包含至少一种根据权利要求1至10中的一项或多项所述的化合物或者根据权利要求11所述的低聚物、聚合物或树枝状大分子以及至少一种其它化合物，所述其它化合物选自荧光发光体、磷光发光体、表现出TADF的发光体、主体材料、电子传输材料、电子注入材料、空穴传导材料、空穴注入材料、电子阻挡材料和空穴阻挡材料。13. A composition comprising at least one compound according to one or more of claims 1 to 10 or an oligomer, polymer or dendrimer according to claim 11 and at least one further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF, host materials, electron transport materials, electron injection materials, hole conducting materials, hole injection materials, electron blocking materials and hole blocking materials. 14.一种用于制备根据权利要求1至10中的一项或多项所述的化合物的方法，其特征在于合成具有氨基基团的基础骨架，并且引入至少一个芳族或杂芳族基团。14. A process for preparing compounds according to one or more of claims 1 to 10, characterized in that a basic skeleton having amino groups is synthesized and at least one aromatic or heteroaromatic group is introduced. 15.根据权利要求1至10中的一项或多项所述的化合物或者根据权利要求11所述的低聚物、聚合物或树枝状大分子在电子器件中的用途。15. Use of a compound according to one or more of claims 1 to 10 or an oligomer, polymer or dendrimer according to claim 11 in an electronic device. 16.一种电子器件，所述电子器件包含至少一种根据权利要求1至10中的一项或多项所述的化合物或者根据权利要求11所述的低聚物、聚合物或树枝状大分子。16 . An electronic device comprising at least one compound according to one or more of claims 1 to 10 or an oligomer, polymer or dendrimer according to claim 11 . 17.根据权利要求16所述的电子器件，所述电子器件为有机电致发光器件，其特征在于根据权利要求1至10中的一项或多项所述的化合物或者根据权利要求11所述的低聚物、聚合物或树枝状大分子用作主体材料、电子传输材料、电子注入材料、空穴传导材料、空穴注入材料、电子阻挡材料、空穴阻挡材料。17. The electronic device according to claim 16, which is an organic electroluminescent device, characterized in that the compound according to one or more of claims 1 to 10 or the oligomer, polymer or dendrimer according to claim 11 is used as a host material, electron transport material, electron injection material, hole conduction material, hole injection material, electron blocking material or hole blocking material.
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