Organic electroluminescent device

Abstract

The present invention relates to an organic electroluminescent device containing a mixture comprising an electron-transporting host material and a hole-transporting host material, as well as to a formulation containing the mixture of host materials and a mixture containing the host material, wherein the electron-transporting host material corresponds to a compound of formula (1) selected from the class of dibenzofuran or dibenzothiophene derivatives containing a substituted pyridine, pyrimidine or triazine unit and a further substituted dibenzofuran or dibenzothiophene unit.

Description

[Technical Field]

[0001] The present invention relates to an organic electroluminescent device comprising a mixture comprising an electron-transporting host material and a hole-transporting host material, as well as to a formulation comprising the mixture of host materials and a mixture comprising the host material, wherein the electron-transporting host material corresponds to a compound of formula (1) from the class of dibenzofuran or dibenzothiophene derivatives containing a substituted pyridine, pyrimidine or triazine unit and a further substituted dibenzofuran or dibenzothiophene unit.

[0002] The structures of organic electroluminescent devices (e.g., OLEDs—organic light-emitting diodes or OLECs—organic light-emitting electrochemical cells) in which organic semiconductors are used as functional materials have been known for some time. The light-emitting materials used here include, in addition to fluorescent emitters, increasingly organometallic complexes that exhibit phosphorescence rather than fluorescence. For quantum-mechanical reasons, the use of organometallic compounds as phosphorescent emitters can increase energy and power efficiency by up to four times. However, in general, there is still a need for improvements in OLEDs, especially those that exhibit triplet emission (phosphorescence), for example, in terms of efficiency, operating voltage, and lifetime.

[0003] The properties of organic electroluminescent devices are not only determined by the luminescent material used.Here, other materials used are also particularly important, such as host and matrix materials, hole blocking materials, electron transport materials, hole transport materials, and electron or exciton blocking materials, and among these, especially host or matrix materials.Improvement of these materials can lead to significant improvement of electroluminescent devices.

[0004] Host materials for use in organic electronic devices are well known to those skilled in the art. The term "matrix material" is also frequently used in the prior art when referring to a host material for a phosphorescent emitter. This terminology is also applicable to the present invention. During this time, many host materials for both fluorescent and phosphorescent electronic devices have been developed.

[0005] A further means of improving the performance data of electronic devices, especially organic electroluminescent devices, is to use a combination of two or more materials, especially host or matrix materials.

[0006] US 6,392,250 B1 discloses the use of a mixture of an electron transport material, a hole transport material and a fluorescent emitter in the light-emitting layer of an OLED, which can improve the lifetime of the OLED compared to the prior art.

[0007] US 6,803,720 B1 discloses the use of a mixture comprising a phosphorescent emitter and a hole transport material and an electron transport material in the light emitting layer of an OLED, both of which are small organic molecules.

[0008] According to KR20120129733, for example, a compound containing two dibenzothiophene units can be used in the light-emitting layer.

[0009] WO2011088877 describes certain heterocyclic compounds that can be used as light-emitting compounds or as host materials or hole-transporting materials in organic light-emitting devices.

[0010] According to WO2015169412, triazine-dibenzofuran-carbazole derivatives and triazine-dibenzothiophene-carbazole derivatives can be used, for example, as host materials in the light-emitting layer.

[0011] According to WO2015105251, it is possible to use dibenzofuran-dibenzofuran derivatives, for example, as host materials in the light-emitting layer.

[0012] US9771373 describes certain carbazole derivatives as host materials in the light-emitting layer of electroluminescent devices which can be used together with further host materials.

[0013] KR20160046077 describes specific triazine-dibenzofuran-carbazole and triazine-dibenzothiophene-carbazole derivatives in the light-emitting layer together with additional host materials and specific light emitters. Here, the carbazole is bonded to the dibenzofuran or dibenzothiophene unit via a nitrogen atom.

[0014] KR20170113318 describes certain heterocyclic compounds that can be used as host materials in the emissive layer of organic light-emitting devices.

[0015] CN107973786 describes triazine-dibenzofuran-carbazole and triazine-dibenzothiophene-carbazole compounds. The triazine substituent is attached to the 1-position of the dibenzofuran / dibenzothiophene either directly or via a linker. The carbazole derivative is attached to the 6-position of the dibenzofuran / dibenzothiophene either directly via the nitrogen atom or via a linker. It is further reported that these materials can be mixed with biscarbazole H2 in a ratio of 10:90 to 90:10.

[0016] US2018337348 describes an electronic device that includes two host materials, for example those listed in Table 2, in an emissive layer.

[0017] WO2018174679 describes an electronic device that includes two host materials, for example those listed in Table 19, in an emissive layer.

[0018] KR20180061076 describes an electronic device that includes two host materials, for example those listed in Table 1, in an emissive layer.

[0019] US2019013490 describes an electronic device that includes two host materials, for example those listed in Table 3, in an emissive layer.

[0020] US20190006590 describes an electronic device comprising a specific sequence of two light-emitting layers, each containing two host materials. The first light-emitting layer comprises Host 1-1 and Host 1-2. The second light-emitting layer comprises Host 2-1 and Host 2-2, where Host 1-2 and Host 2-1 are the same material. Claims 7 and 8 describe a specific biscarbazole as Host Material 1-2. Claims 9 and 10 describe a specific triazine derivative as Host Material 2-2.

[0021] US2019047991 describes doubly substituted triazine-dibenzofuran derivatives and describes their use as organic materials in organic light-emitting devices.

[0022] WO19031679 describes an organic light-emitting device containing a first host material comprising a doubly substituted triazine-dibenzofuran derivative and a second host material in the light-emitting layer.

[0023] US2019037012 describes an organic light-emitting device that includes a first host material containing two dibenzofuran units bonded to each other and a second host material, such as a biscarbazole, in an emissive layer.

[0024] WO2020022779 describes an organic light-emitting device comprising in an emissive layer a first host material comprising three dibenzofuran and / or dibenzothiophene units bonded to each other, and a second host material, for example, a biscarbazole.

[0025] WO2020022860 describes an organic light-emitting device containing a deuterated triazine derivative and a biscarbazole derivative in the light-emitting layer.

[0026] However, when using these materials or mixtures of materials, there is still a need for improvement, especially with regard to the efficiency, operating voltage and / or lifetime of organic electroluminescent devices.

[0027] The problem addressed by the present invention is therefore that of providing host material combinations that are suitable for use in organic electroluminescent devices, in particular fluorescent or phosphorescent OLEDs, and that lead to good device properties, in particular in terms of improved lifetime, and to provide corresponding electroluminescent devices.

[0028] It has now been discovered that the combination of at least one compound of formula (1) as a first host material and at least one hole-transporting compound of formula (2) as a second host material in the light-emitting layer of an organic electroluminescent device solves this problem and eliminates the drawbacks of the prior art. The use of such a material combination to prepare the light-emitting layer in an organic electroluminescent device leads to very good properties of these devices, especially in terms of lifetime, and especially in terms of comparable or improved efficiency and / or operating voltage. These advantages are also particularly evident in the presence of a light-emitting component in the light-emitting layer, especially in combination with an emitter of formula (III) at a concentration of 2% to 25% by weight.

[0029] Therefore, the present invention first provides an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer containing at least one light-emitting layer, wherein the at least one light-emitting layer comprises at least one compound of formula (1) as host material 1 and at least one compound of formula (2) as host material 2.

[0030] [ka]

[0031] (wherein the symbols and subscripts used are as follows: X may be the same or different in each case, and CR 0 or N, where at least one symbol X is N; X2 may be the same or different in each case, CH, CR 1 or N, where up to two symbols X2 may be N; Y and Y1, in each occurrence, are the same or different and are selected from O and S; L, in each occurrence, is the same or different and is a single bond or an aromatic ring system having 6 to 30 aromatic ring atoms; L1, in each occurrence, is the same or different and is a single bond or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms; R in each case 0 are independently H, D, or an unsubstituted or partially or fully deuterated aromatic ring system having 6 to 18 carbon atoms; R* in each occurrence is independently D or an aromatic or heteroaromatic ring system having 6 to 18 carbon atoms, which may be partially or fully deuterated; R# may be the same or different in each case; D, F, Cl, Br, I, CN, NO2, C(=O)R 2 , P(=O)(Ar1)2, P(Ar1)2, B(Ar1)2, Si(Ar1)3, Si(R 2 ) 3, a linear alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms (each of which may be one or more R 2 radicals) (wherein one or more non-adjacent CH groups are optionally substituted by R 2 C=CR 2, Si(R 2 )2, C=O, C=S, C=NR 2 , P(=O)(R 2 ), SO, SO2, NR 2 , O, S or CONR 2 and one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO), having 5 to 40 aromatic ring atoms, in each case one or more R 2 Aromatic or heteroaromatic ring systems, optionally substituted by radicals, having 5 to 40 aromatic ring atoms and one or more R 2 an aryloxy or heteroaryloxy group optionally substituted by a radical, or an aryloxy group having 5 to 40 aromatic ring atoms and one or more R 2 aralkyl or heteroaralkyl groups optionally substituted by a radical; R in each occurrence is the same or different and is selected from a CN group, an aromatic ring system having 6 to 40 aromatic ring atoms, and a heteroaromatic ring system having 10 to 40 aromatic ring atoms, wherein the ring system is selected from one or more R 2 optionally substituted by radicals, the heteroaromatic ring system being bonded via N when the heteroaromatic ring system contains a nitrogen atom; R 1 are in each occurrence the same or different and are selected from the group consisting of CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms; at the same time, two substituents R attached to the same carbon atom or adjacent carbon atoms 1 but one or more R 2 It is possible to form monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring systems, which may be optionally substituted by radicals; R2 are the same or different in each case and are H, D, F, Cl, Br, I, CN, NO2, N(Ar1)2, NH2, N(R 3 )2, C(=O)Ar1, C(=O)H, C(=O)R 3 , P(═O)(Ar1)2, a linear alkyl, alkoxy, or thioalkyl group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 carbon atoms, or an alkenyl or alkynyl group having 2 to 40 carbon atoms (each of which may be one or more R 3 radicals) (wherein one or more non-adjacent CH groups are substituted by HC=CH, R 3 C=CR 3 , C≡C, Si(R 3 )2, Ge(R 3 )2, Sn(R 3 )2, C=O, C=S, C=Se, C=NR 3 , P(=O)(R 3 ), SO, SO2, NH, NR 3 , O, S, CONH or CONR 3 and one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO), having 5 to 60 aromatic ring atoms, in each case one or more R 3 Aromatic or heteroaromatic ring systems, optionally substituted by radicals, having 5 to 60 aromatic ring atoms and one or more R 3 aryloxy or heteroaryloxy groups optionally substituted by radicals, or combinations of these systems; two or more adjacent substituents R 2 but one or more R 3 optionally capable of forming monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring systems, optionally substituted by radicals; R 3are in each occurrence the same or different and are selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, or CN, and may be substituted by one or more alkyl groups, each having 1 to 4 carbon atoms; 3 The substituents, taken together, may form a monocyclic or polycyclic aliphatic ring system; Ar1 in each occurrence is the same or different and has 5 to 30 aromatic ring atoms and one or more non-aromatic R 3 at the same time, two Ar radicals attached to the same nitrogen, phosphorus or boron atom are also joined by a single bond or an N(R 3 ), C(R 3 ) 2, may be crosslinked to each other by a bridge selected from O and S; Ar2 and Ar3 in each instance each independently have 5 to 40 aromatic ring atoms and one or more R 2 an aryl or heteroaryl group optionally substituted by a radical; A in each instance is independently represented by formula (3) or (4),

[0032] [ka]

[0033] is the basis of; Ar, in each occurrence, is independently an aryl group having 6 to 40 aromatic ring atoms, optionally substituted with one or more R# radicals, or a heteroaryl group having 5 to 40 aromatic ring atoms, optionally substituted with one or more R# radicals; * indicates the site of attachment to formula (2); a, b, and c at each occurrence are each independently 0 or 1, where the sum of the indices a+b+c at each occurrence is 1; m and o in each occurrence are independently 0, 1, 2, 3, or 4; n and p in each occurrence are each independently 0, 1, 2, or 3; and q, r, s, and t, each occurring independently, are 0 or 1.

[0034] The present invention further provides a method for producing an organic electroluminescent device, a mixture comprising at least one compound of formula (1) and at least one compound of formula (2), a specific material combination, and a formulation containing such a mixture or material combination. The corresponding preferred embodiments described below also form part of the subject matter of the present invention. The surprising advantageous effect is achieved through the specific selection of the compound of formula (1) and the compound of formula (2).

[0035] The organic electroluminescent device of the present invention is, for example, an organic light-emitting transistor (OLET), an organic field-quenched device (OFQD), an organic light-emitting electrochemical cell (OLEC, LEC, LEEC), an organic laser diode (O-laser), or an organic light-emitting diode (OLED).The organic electroluminescent device of the present invention is particularly an organic light-emitting diode or an organic light-emitting electrochemical cell.The device according to the present invention is more preferably an OLED.

[0036] The organic layers of a device according to the present invention, which contains an emissive layer containing a material combination of at least one compound of formula (1) and at least one compound of formula (2), as described above or below, preferably comprise, in addition to the emissive layer (EML), a hole-injection layer (HIL), a hole-transport layer (HTL), an electron-transport layer (ETL), an electron-injection layer (EIL), and / or a hole-blocking layer (HBL). The device may also comprise multiple layers from this group selected from the EML, HIL, HTL, ETL, EIL, and HBL.

[0037] However, the device may also include other layers formed from inorganic or entirely inorganic materials.

[0038] The light-emitting layer containing at least one compound of formula (1) and at least one compound of formula (2) is preferably a phosphorescent layer characterized by comprising at least one phosphorescent emitter in addition to the host material combination of the compounds of formula (1) and formula (2) as described above. Suitable selection of emitters and preferred emitters are described below.

[0039] An aryl group in the context of this invention contains 6 to 40 aromatic ring atoms, preferably carbon atoms. A heteroaryl group in the context of this invention contains 5 to 40 aromatic ring atoms, where the ring atoms include carbon atoms and at least one heteroatom, provided that the total of carbon atoms and heteroatoms is at most 5. The heteroatoms are preferably selected from N, O, and / or S. An aryl or heteroaryl group is understood here to mean either a simple aromatic ring derived from benzene, i.e., phenyl, or a simple heteroaromatic ring derived, for example, from pyridine, pyrimidine, or thiophene, or a fused aryl or heteroaryl group derived, for example, from naphthalene, anthracene, phenanthrene, quinoline, or isoquinoline. Thus, an aryl group having 6 to 18 carbon atoms is preferably phenyl, naphthyl, phenanthryl, or triphenylenyl, with no restrictions on the attachment of the aryl group as a substituent. An aryl or heteroaryl group in the context of this invention carries one or more R radicals, where the substituent R is described below.

[0040] Aromatic ring systems in the context of this invention contain from 6 to 40 carbon atoms in the ring system. Aromatic ring systems also include aryl groups as defined above.

[0041] The aromatic ring system having 6 to 18 carbon atoms is preferably selected from phenyl, fully deuterated phenyl, biphenyl, naphthyl, phenanthryl and triphenylenyl.

[0042] A heteroaromatic ring system in the context of the present invention contains 5 to 40 ring atoms and at least one heteroatom. Preferred heteroaromatic ring systems have 10 to 40 ring atoms and at least one heteroatom. Heteroaromatic ring systems also include heteroaryl groups as described above. The heteroatoms in a heteroaromatic ring system are preferably selected from N, O and / or S.

[0043] In the context of the present invention, aromatic or heteroaromatic ring systems are not necessarily limited to aryl or heteroaryl groups, but may also be interrupted by non-aromatic units (preferably less than 10% of atoms other than H), such as carbon, nitrogen or oxygen atoms, or carbonyl groups.For example, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc. are also considered aromatic or heteroaromatic ring systems in the context of the present invention, as are systems in which two or more aryl groups are interrupted, for example, by linear or cyclic alkyl groups or by silyl groups.In addition, systems in which two or more aryl or heteroaryl groups are directly bonded to each other, such as biphenyl, terphenyl, quaterphenyl or bipyridine, are also included in the definition of aromatic or heteroaromatic ring systems.

[0044] Aromatic or heteroaromatic ring systems having 5 to 40 aromatic ring atoms and which may be joined via any desired position include, for example, benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, benzofluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofenone, fluorene, cis- or trans-monobenzoindenofluorene, cis- or trans-dibenzoindenofluorene, truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, indolocarbazole, indenocarbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinolinol, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazineimidazole, quinoxalineimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine , quinoxaline, 1,5-diazaanthracene, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazapyrylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorubine, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,It is understood to mean groups derived from 4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine and benzothiadiazole.

[0045] The abbreviation Ar1 is in each case the same or different, has 5 to 30 aromatic ring atoms and one or more non-aromatic R 3 at the same time, two Ar radicals attached to the same nitrogen, phosphorus or boron atom are also joined by a single bond or an N(R 3 ), C(R 3 ) 2, O and S, wherein R 3 Radical or Substituent R 3 has the definition as described above or hereinafter. Preferably, Ar1 is an aryl group having 6 to 40 aromatic ring atoms as described above. Most preferably, Ar1 is an aryl group having one or more non-aromatic R 3 Ar1 is preferably unsubstituted phenyl, which may be substituted by a radical.

[0046] The abbreviation Ar2 in each instance independently represents a group having 5 to 40 aromatic ring atoms and one or more R 2 an aryl or heteroaryl group optionally substituted by a radical, where R 2 Radical or Substituent R 2 has the definition as given above or hereinafter. The details given in relation to aryl and heteroaryl groups having 5 to 40 aromatic ring atoms apply correspondingly here.

[0047] The abbreviation Ar3 in each instance independently represents a group having 5 to 40 aromatic ring atoms and one or more R 2an aryl or heteroaryl group optionally substituted by a radical, where R 2 Radical or Substituent R 2 has the definition as given above or hereinafter. The details given in relation to aryl and heteroaryl groups having 5 to 40 aromatic ring atoms apply correspondingly here.

[0048] The abbreviation Ar in each case is independently in each case an aryl group having 6 to 40 aromatic ring atoms and optionally substituted by one or more R# radicals, or a heteroaryl group having 5 to 40 aromatic ring atoms and optionally substituted by one or more R# radicals; the details given above for the aryl group or heteroaryl group apply accordingly. The R# radicals have the definition as given above or below. The abbreviation Ar in each case preferably is independently in each case an aryl group having 6 to 40 aromatic ring atoms and optionally substituted by one or more R# radicals, or a heteroaryl group having 5 to 40 aromatic ring atoms and containing O or S and optionally substituted by one or more R# radicals, and the details given above or below for the aryl group, heteroaryl group and R# apply accordingly.

[0049] A cyclic alkyl, alkoxy or thioalkyl group in the context of this invention is understood to mean a monocyclic, bicyclic or polycyclic group.

[0050] In the context of the present invention, linear, branched or cyclic C1-C 20Examples of alkyl groups include methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl, s-butyl, t-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neopentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neohexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl , 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl, 1-bicyclo[2.2.2]octyl, 2-bicyclo[2.2.2]octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, 1,1-dimethyl-n-hex-1-yl, 1,1-dimethyl-n-heptyl -1-yl, 1,1-dimethyl-n-oct-1-yl, 1,1-dimethyl-n-dec-1-yl, 1,1-dimethyl-n-dodec-1-yl, 1,1-dimethyl-n-tetradec-1-yl, 1,1-dimethyl-n-hexadec-1-yl, 1,1-dimethyl-n-octadec-1-yl, 1,1-diethyl-n-hex-1-yl, 1,1-diethyl-n-hept-1-yl, 1,1-diethyl-n-oct-1-yl, 1,1-diethyl-n-dec-1-yl, It is understood to mean the 1,1-diethyl-n-dodec-1-yl, 1,1-diethyl-n-tetradec-1-yl, 1,1-diethyl-n-hexadec-1-yl, 1,1-diethyl-n-octadec-1-yl, 1-(n-propyl)cyclohex-1-yl, 1-(n-butyl)cyclohex-1-yl, 1-(n-hexyl)cyclohex-1-yl, 1-(n-octyl)cyclohex-1-yl and 1-(n-decyl)cyclohex-1-yl radicals.

[0051] Straight or branched C1-C 20An alkoxy group is understood to mean, for example, methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy or 2-methylbutoxy.

[0052] Straight chain C1~C 20 A thioalkyl group is understood to mean, for example, an S-alkyl group, such as thiomethyl, 1-thioethyl, 1-thio-i-propyl, 1-thio-n-propyl, 1-thio-i-butyl, 1-thio-n-butyl or 1-thio-t-butyl.

[0053] An aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms means O-aryl or O-heteroaryl, which means that the aryl or heteroaryl group is attached via an oxygen atom, where the aryl or heteroaryl group is defined as above.

[0054] An aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms means that an alkyl group as defined above is substituted with an aryl or heteroaryl group, where the aryl or heteroaryl group is defined as above.

[0055] Phosphorescent emitters in the context of the present invention are compounds that emit light from excited states of higher spin multiplicity, i.e., spin states greater than 1, in particular from excited triplet states. In the context of this application, all luminescent complexes containing transition metals or lanthanides should be considered as phosphorescent emitters. A more precise definition will be given later.

[0056] When a phosphorescent emitter is used in a host material of the emissive layer, the host material preferably comprises at least one compound of formula (1) as described above or as preferred below, and at least one compound of formula (2) as described above or as preferred below. It is preferred that the triplet energy of the host material is not significantly lower than that of the phosphorescent emitter. Regarding the triplet level, it is preferred that T1(emitter)-T1(matrix) be 0.2 eV or less, more preferably 0.15 eV or less, and most preferably 0.1 eV or less. Here, T1(matrix) is the triplet level of the matrix material in the emissive layer, and this condition is applicable to each of the two matrix materials, and T1(emitter) is the triplet level of the phosphorescent emitter. When the emissive layer contains more than two matrix materials, the above relationship is preferably also applicable to each of the additional matrix materials.

[0057] The host material 1 and its preferred embodiments in the device of the present invention are described below: The preferred embodiments of the host material 1 of formula (1) also apply to the mixtures and / or formulations of the present invention.

[0058] In the compounds of formula (1), the symbol Y represents O or S.

[0059] In a preferred embodiment of the compounds of formula (1), the symbol Y preferably represents O.

[0060] Thus, the present invention further provides an electroluminescent device as described above, wherein Y in Host Material 1 is O.

[0061] Compounds of formula (1) in which Y is preferably O are represented by formulae (1a) and (1b)

[0062] [ka]

[0063] wherein Ar2, Ar3, L1, R*, n, m, L, R, p, Y1 and o have the definitions given above or preferably below.

[0064] In a preferred embodiment of the compounds of formula (1), the symbol Y is preferably S.

[0065] Thus, the present invention further provides an electroluminescent device as described above, wherein Y in Host Material 1 is S.

[0066] Compounds of formula (1) in which Y is preferably S are represented by formulae (1c) and (1d)

[0067] [ka]

[0068] wherein Ar2, Ar3, L1, R*, n, m, L, R, p, Y1 and o have the definitions given above or preferably below.

[0069] In a preferred embodiment of the compounds of formula (1), (1a), (1b), (1c) and (1d) or the host materials of formula (1), (1a), (1b), (1c) and (1d), the symbol X is CR 0 or N, where at least one X group is N.

[0070] Therefore, the substituent

[0071] [ka]

[0072] has the following definition, where * indicates the site of attachment to the dibenzofuran or dibenzothiophene via L1, and R 0 , Ar2 and Ar3 have the definitions given above or the definitions given as preferred:

[0073] [ka]

[0074] It has.

[0075] In the host material 1, X is preferably N in two cases, and one X is CR 0 or all X's are N's.

[0076] The present invention therefore further provides an electroluminescent device as described above or as preferred, wherein in the host material 1, the symbol X is preferably N in two cases and one X is CR 0 or the symbol X is N in three cases.

[0077] In Host Material 1, all X's are more preferably N, where R 0 has the definition given above or given below.

[0078] R in each case 0 are the same or different and are preferably selected from the group of H, D or unsubstituted or partially or fully deuterated aromatic ring systems having 6 to 18 carbon atoms. 0 is preferably H, D or an unsubstituted aromatic ring system having 6 to 18 carbon atoms. 0 is more preferably H.

[0079] In preferred embodiments of the compounds of formula (1), (1a), (1b), (1c) and (1d) or the host materials of formula (1), (1a), (1b), (1c) and (1d), the linker L1 is a single bond or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms.

[0080] In a preferred embodiment of the compounds of formula (1), (1a), (1b), (1c) and (1d) or the host materials of formula (1), (1a), (1b), (1c) and (1d), the linker L1 is preferably a bond, or one of L-1 to L-20.

[0081] [ka]

[0082] [ka]

[0083] is a linker selected from the group:

[0084] In preferred embodiments of the compounds of formula (1), (1a), (1b), (1c) and (1d) or the host materials of formula (1), (1a), (1b), (1c) and (1d), the linker L1 is more preferably a bond or a linker selected from the group of L-2 and L-3.

[0085] In preferred embodiments of the compounds of formula (1), (1a), (1b), (1c) and (1d) or the host materials of formula (1), (1a), (1b), (1c) and (1d), the linker L1 is most preferably a bond.

[0086] In preferred embodiments of the compounds of formula (1), (1a), (1b), (1c) and (1d) or the host materials of formula (1), (1a), (1b), (1c) and (1d), the linker L is a single bond or an aromatic ring system having from 6 to 30 aromatic ring atoms.

[0087] In preferred embodiments of the compounds of formula (1), (1a), (1b), (1c) and (1d) or the host materials of formula (1), (1a), (1b), (1c) and (1d), the linker L is preferably a bond or a linker selected from the group L-1 to L-20 as described above.

[0088] In preferred embodiments of the compounds of formula (1), (1a), (1b), (1c) and (1d) or the host materials of formula (1), (1a), (1b), (1c) and (1d), the linker L is more preferably a bond or a linker selected from the group of L-2 and L-3.

[0089] In preferred embodiments of the compounds of formula (1), (1a), (1b), (1c) and (1d) or host materials of formula (1), (1a), (1b), (1c) and (1d), the linker L is most preferably a bond.

[0090] In preferred embodiments of the compounds of formula (1), (1a), (1b), (1c) and (1d) or host materials of formula (1), (1a), (1b), (1c) and (1d), o is preferably 0, 1 or 2, more preferably 0 or 1, and most preferably 1, wherein R has the preferred definitions given above or below.

[0091] In preferred embodiments of the compounds of formula (1), (1a), (1b), (1c) and (1d) or host materials of formula (1), (1a), (1b), (1c) and (1d), p is preferably 0 or 1, more preferably 0, and wherein R has the preferred definitions given above or below.

[0092] In preferred embodiments of the compounds of formula (1), (1a), (1b), (1c) and (1d) or host materials of formula (1), (1a), (1b), (1c) and (1d), m is preferably 0, 1 or 2, more preferably 0 or 1, and R* has the preferred definition given above or below.

[0093] In preferred embodiments of the compounds of formula (1), (1a), (1b), (1c) and (1d) or host materials of formula (1), (1a), (1b), (1c) and (1d), n is preferably 0 or 1, more preferably 0, and wherein R* has the preferred definition given above or below.

[0094] R* in each occurrence is the same or different and is preferably selected from the group consisting of D or aromatic or heteroaromatic ring systems having 6 to 18 carbon atoms, which may be partially or fully deuterated. R* in each occurrence is preferably phenyl, 1,3-biphenyl, 1,4-biphenyl, dibenzofuranyl, or dibenzothiophenyl. R* in each occurrence is more preferably phenyl, 1,3-biphenyl, 1,4-biphenyl, or dibenzofuranyl.

[0095] R in each occurrence is the same or different and is selected from a CN group, an aromatic ring system having 6 to 40 aromatic ring atoms, and a heteroaromatic ring system having 10 to 40 aromatic ring atoms, wherein the ring system is selected from one or more R 2 The heteroaromatic ring system may be bonded through N when the heteroaromatic ring system contains a nitrogen atom. R in each instance is preferably independently phenyl, triphenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, N-carbazolyl, fluorenyl, spirobifluorenyl, indolocarbazolyl, indenocarbazolyl, which may be substituted by one or more radicals R 2 R may be substituted with N-carbazolyl. N-carbazolyl is preferably substituted with phenyl. R in each case is more preferably independently phenyl, triphenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, N-carbazolyl, fluorenyl, spirobifluorenyl, indolocarbazolyl, indenocarbazolyl, or phenyl-substituted N-carbazolyl. R in each case is most preferably independently phenyl, dibenzofuranyl, or phenyl-substituted N-carbazolyl.

[0096] The compound of formula (1a) is a preferred embodiment of the compound of formula (1) and host material 1.

[0097] In preferred embodiments of the compounds of formula (1), (1a), (1b), (1c) and (1d) or the host materials of formula (1), (1a), (1b), (1c) and (1d), Y1 is O or S, preferably O.

[0098] In preferred embodiments of the compounds of formula (1), (1a), (1b), (1c) and (1d) or host materials of formula (1), (1a), (1b), (1c) and (1d), each Ar2 is preferably independently an aryl group having 6 to 40 carbon atoms as described above or as preferred, which is selected from one or more R 2 or a heteroaryl group having 10 to 40 carbon atoms as described above (which may be substituted by one or more R 2 radicals), where two or more R 2 A radical is one or more R 3 It is possible to form mono- or polycyclic aliphatic, aromatic or heteroaromatic ring systems which may be optionally substituted by radicals.

[0099] Attachment of an aryl or heteroaryl group is not limited and may be via a carbon atom or a heteroatom, such as a nitrogen atom.

[0100] Ar2 may preferably be selected from the following group Ar-1 to Ar-19, where R 2 and Ar1 have the definitions specified or preferred above, and R 2 Alternatively, direct bonding of two heteroatoms to each other by Ar1 is excluded.

[0101] [ka]

[0102] [ka]

[0103] [ka]

[0104] The dotted lines indicate the binding sites for the radicals of formulas (1), (1a), (1b), (1c) and (1d).

[0105] More preferably, Ar2 is Ar-1, Ar-2, Ar-3, Ar-6, Ar-14, Ar-17 and Ar-18, where R 2 and Ar1 has the definitions specified or preferred above.

[0106] In preferred embodiments of the compounds of formula (1), (1a), (1b), (1c) and (1d) or host materials of formula (1), (1a), (1b), (1c) and (1d), each Ar3 is preferably independently an aryl group having 6 to 40 carbon atoms as described above or as preferred, which may be one or more R 2 or a heteroaryl group having 10 to 40 carbon atoms as described above (which may be substituted by one or more R 2 radicals), where two or more R 2 A radical is one or more R 3 It is possible to form mono- or polycyclic aliphatic, aromatic or heteroaromatic ring systems which may be optionally substituted by radicals.

[0107] Attachment of an aryl or heteroaryl group is not limited and may be via a carbon atom or a heteroatom, such as a nitrogen atom.

[0108] Ar3 may preferably be selected from the following group Ar-1 to Ar-19, where R 2 and Ar1 have the definitions specified or preferred above, and R 2Alternatively, direct bonding of two heteroatoms to each other by Ar1 is excluded.

[0109] More preferably, Ar3 is Ar-1, Ar-2, or Ar-3, where R 2 and Ar1 has the definitions specified or preferred above.

[0110] R in the substituents of formulae Ar-1 to Ar-19 as described above 2 is preferably H, D, CN, has 5 to 40 aromatic ring atoms, and in each case is one or more R 3 The ring system is selected from the group of aromatic or heteroaromatic ring systems optionally substituted by radicals.

[0111] R in the substituents of formulae Ar-1 to Ar-19 as described above 2 is more preferably H, D, phenyl or N-carbazolyl.

[0112] Ar1 in the substituents of the formulae Ar-13 to Ar-16 as described above is preferably phenyl.

[0113] The attachment of the groups attached via the linker L or L in the compounds of formula (1), (1a), (1b), (1c) and (1d) or preferred compounds of formula (1), (1a), (1b), (1c) and (1d) is not limited here and may be via any carbon atom.

[0114] More preferably, the substituent

[0115] [ka]

[0116] is attached at position 1 to a radical of formula (1), (1a), (1b), (1c) or (1d) via a linker L1, which in the case of a compound of formula (1) is

[0117] [ka]

[0118] wherein Ar2, Ar3, L1, R*, n, m, Y, L, R, p, o and Y1 have the definitions given above or as preferred.

[0119] Therefore, the substituent

[0120] [ka]

[0121] is a group consisting of substituents P-1 to P-4 and P-6 to P-9:

[0122] [ka]

[0123] wherein * indicates the site of attachment to the linker L, and R, p, o and Y1 have the definitions as previously described or as preferred. and may be linked to the radical of formula (1), (1a), (1b), (1c), (1d) or (1e) via a linker L at any position, as represented by:

[0124] More preferably, P-1 is attached to the linker L.

[0125] More preferably, the substituent

[0126] [ka]

[0127] is attached to the central dibenzofuran or dibenzothiophene at its 6- or 8-position via a linker to the remainder of formula (1), (1a), (1b), (1c), (1d) or (1e), as previously described or referenced as P-1 to P-4 and P-5 to P-9. In the case of compounds of formula (1), this corresponds to formulas (1f) and (1g):

[0128] [ka]

[0129] wherein X, Ar2, Ar3, L1, Y, R*, n, m, L, R, p, o, L and Y1 have the definitions given above or as preferred, substituent

[0130] [ka]

[0131] Similarly, the terms ', ...

[0132] In the compounds of formula (1), (1a), (1b), (1c) and (1d) as described above or as preferred, R 3 is preferably selected independently in each occurrence from the group consisting of H, CN, aromatic or heteroaromatic ring systems having 5 to 40 aromatic ring atoms in which one or more hydrogen atoms may be replaced by D or CN. In the compounds of formulae (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g) as described above or as preferred, R 3 is more preferably independently selected at each occurrence from H, phenyl, or deuterated phenyl.

[0133] Examples of suitable host materials of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g) selected according to the present invention and preferably used in combination with at least one compound of formula (2) in the electroluminescent devices of the present invention are the structures shown in Table 1 below.

[0134] [Table 1-1]

[0135] [Table 1-2]

[0136] [Table 1-3]

[0137] [Table 1-4]

[0138] [Table 1-5]

[0139] [Table 1-6]

[0140] [Table 1-7]

[0141] [Table 1-8]

[0142] [Table 1-9]

[0143] Table 1-10

[0144] Table 1-11

[0145] Table 1-12

[0146] Table 1-13

[0147] Table 1-14

[0148] Table 1-15

[0149] Table 1-16

[0150] Table 1-17

[0151] Table 1-18

[0152] Table 1-19

[0153] Table 1-20

[0154] Table 1-21

[0155] Table 1-22

[0156] Table 1-23

[0157] Table 1-24

[0158] Table 1-25

[0159] Table 1-26

[0160] Table 1-27

[0161] Table 1-28

[0162] Table 1-29

[0163] Table 1-30

[0164] Table 1-31

[0165] Table 1-32

[0166] Table 1-33

[0167] Table 1-34

[0168] Table 1-35

[0169] Table 1-36

[0170] Table 1-37

[0171] Table 1-38

[0172] Table 1-39

[0173] Table 1-40

[0174] Table 1-41

[0175] Table 1-42

[0176] Table 1-43

[0177] Table 1-44

[0178] Table 1-45

[0179] Table 1-46

[0180] Table 1-47

[0181] Table 1-48

[0182] Table 1-49

[0183] Table 1-50

[0184] Table 1-51

[0185] Table 1-52

[0186] Table 1-53

[0187] Table 1-54

[0188] Table 1-55

[0189] Table 1-56

[0190] Table 1-57

[0191] Table 1-58

[0192] Table 1-59

[0193] Table 1-60

[0194] Table 1-61

[0195] Table 1-62

[0196] Table 1-63

[0197] Table 1-64

[0198] Table 1-65

[0199] Table 1-66

[0200]

Table 1-67

[0201] Table 1-68

[0202] Table 1-69

[0203] Table 1-70

[0204] Table 1-71

[0205] Table 1-72

[0206] Table 1-73

[0207] Table 1-74

[0208] Table 1-75

[0209] Table 1-76

[0210] Table 1-77

[0211] Table 1-78

[0212] Table 1-79

[0213] Table 1-80

[0214] [Table 1-81]

[0215] Particularly suitable compounds of formulae (1), (1a), (1b), (1c), (1d), (1e), which are preferably used in combination with at least one compound of formula (2) in the electroluminescent devices of the present invention, are compounds E1 to E54.

[0216] [Table 2-1]

[0217] [Table 2-2]

[0218] [Table 2-3]

[0219] [Table 2-4]

[0220] [Table 2-5]

[0221] [Table 2-6]

[0222] The preparation of compounds of formula (1) or the preferred compounds of Table 1 and compounds E1-E54 is known to those skilled in the art. The compounds may be prepared by synthetic steps known to those skilled in the art, such as bromination, Suzuki coupling, Ullmann coupling, Hartwig-Buchwald coupling, etc. A suitable synthetic method is outlined in Scheme 1 below, where the symbols and indices used have the definitions given above.

[0223] [ka]

[0224] The host material 2 and its preferred embodiments in the device of the present invention are described below: The preferred embodiments of the host material 2 of formula (2) also apply to the mixtures and / or formulations of the present invention.

[0225] The host material 2 is at least one compound of formula (2).

[0226] [ka]

[0227] (wherein the symbols and subscripts used are as follows: A in each instance is independently represented by formula (3) or (4),

[0228] [ka]

[0229] is the basis of; X2 may be the same or different in each case, CH, CR 1 or N, where up to two symbols X2 may be N; * indicates the site of attachment to formula (2); R 1are in each occurrence the same or different and are selected from the group consisting of CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms; at the same time, two substituents R attached to the same carbon atom or adjacent carbon atoms 1 but one or more R 2 It is possible to form monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring systems, which may be optionally substituted by radicals; Ar, in each occurrence, is independently an aryl group having 6 to 40 aromatic ring atoms, optionally substituted with one or more R# radicals; or a heteroaryl group having 5 to 40 aromatic ring atoms, optionally substituted with one or more R# radicals; R# may be the same or different in each case and may be D, F, Cl, Br, I, CN, NO2, C(=O)R 2 , P(=O)(Ar1)2, P(Ar1)2, B(Ar1)2, Si(Ar1)3, Si(R 2 ) 3, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms (each of which may be selected from the group consisting of one or more R 2 radicals) (wherein one or more non-adjacent CH groups are optionally substituted by R 2 C=CR 2 , Si(R 2 )2, C=O, C=S, C=NR 2 , P(=O)(R 2 ), SO, SO2, NR 2 , O, S or CONR 2and one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO), having 5 to 40 aromatic ring atoms, in each case one or more R 2 Aromatic or heteroaromatic ring systems, optionally substituted by radicals, having 5 to 40 aromatic ring atoms and one or more R 2 an aryloxy or heteroaryloxy group optionally substituted by a radical, or an aryloxy group having 5 to 40 aromatic ring atoms and one or more R 2 selected from the group consisting of aralkyl or heteroaralkyl optionally substituted by a radical; R 2 are the same or different in each case and are H, D, F, Cl, Br, I, CN, NO2, N(Ar1)2, NH2, N(R 3 )2, C(=O)Ar1, C(=O)H, C(=O)R 3 , P(═O)(Ar1)2, a linear alkyl, alkoxy, or thioalkyl group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 carbon atoms, or an alkenyl or alkynyl group having 2 to 40 carbon atoms (each of which may be one or more R 3 radicals) (wherein one or more non-adjacent CH groups are substituted by HC=CH, R 3 C=CR 3 , C≡C, Si(R 3 )2, Ge(R 3 )2, Sn(R 3 )2, C=O, C=S, C=Se, C=NR 3 , P(=O)(R 3 ), SO, SO2, NH, NR 3 , O, S, CONH or CONR 3 and one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO), having 5 to 60 aromatic ring atoms, in each case one or more R 3Aromatic or heteroaromatic ring systems, optionally substituted by radicals, having 5 to 60 aromatic ring atoms and one or more R 3 aryloxy or heteroaryloxy groups optionally substituted by radicals, or combinations of these systems; two or more adjacent substituents R 2 but one or more R 3 optionally capable of forming monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring systems, optionally substituted by radicals; R 3 are in each occurrence the same or different and are selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, or CN, and may be substituted by one or more alkyl groups, each having 1 to 4 carbon atoms; 3 The substituents, taken together, may form a monocyclic or polycyclic aliphatic ring system; Ar1 in each occurrence is the same or different and has 5 to 30 aromatic ring atoms and one or more non-aromatic R 3 at the same time, two Ar radicals attached to the same nitrogen, phosphorus or boron atom are also joined by a single bond or an N(R 3 ), C(R 3 ) 2, may be crosslinked to each other by a bridge selected from O and S; a, b, and c at each occurrence are each independently 0 or 1, where the sum of the indices a+b+c at each occurrence is 1; In each instance, q, r, s, and t are each independently 0 or 1.

[0230] In one embodiment of the invention, for a device of the invention, a compound of formula (2) as described above is selected and used in the emissive layer together with a compound of formula (1) as described above or as preferred, or together with a compound of Table 1 or compounds E1 to E54.

[0231] In compounds of formula (2), a, b, and c at each occurrence are each independently 0 or 1, where the sum of the indices a+b+c at each occurrence is 1. c is preferably defined as 1.

[0232] The compound of formula (2) is represented by the following formulae (2a), (2b) and (2c):

[0233] [ka]

[0234] (In the formula, A, R 1 , q, r, s, and t have the definitions given above or below) Preferred herein are compounds of formula (2a):

[0235] Thus, the present invention further provides an organic electroluminescent device as described above or as preferred, wherein the host material 2 corresponds to a compound of formula (2a), (2b) or (2c).

[0236] R in the compounds of formula (2) and formula (2a) to (2c) or preferred compounds of formula (2) and formula (2a) to (2c) as described above 1are in each occurrence the same or different and are selected from the group consisting of CN, a linear alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms; at the same time, two substituents R attached to the same carbon atom or adjacent carbon atoms 1 but one or more R 2 It is possible to form mono- or polycyclic aliphatic, aromatic or heteroaromatic ring systems which may be optionally substituted by radicals.

[0237] Two or more R's 1 If the radicals are attached to adjacent carbon atoms, the monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system is preferably one of the following: (S-1) to (S-4)

[0238] [ka]

[0239] (Wherein, Ar1 and R 2 has the definition given above or as preferred, and # represents the site of attachment to the adjacent position identified by X2 in the remainder of each structure, e.g., compounds of formula (2), (2a), (2b), and (2c). Particularly preferred here are the selections (S-1) to (S-2).

[0240] R in the compounds of formula (2) and formula (2a) to (2c) or preferred compounds of formula (2) and formula (2a) to (2c) as described above 1are in each case the same or different and are preferably selected from the group consisting of CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms. 1 are more preferably independently CN or an aryl group having 6 to 40 carbon atoms as described above. 1 is more preferably independently phenyl.

[0241] In the compounds of formula (2), (2a), (2b) or (2c), the sum of the indices q+r+s is preferably 0, 1 or 2, where R 1 In the compounds of formula (2), (2a), (2b) or (2c), the sum of the indices q+r+s is preferably 0 or 1, where R 1 has the definition given above.

[0242] In the compounds of formula (2), (2a), (2b) or (2c), q, r and s are preferably 0 or 1. Preferably, when the sum of the indices q+r+s is 1, q is 1. Preferably, q, r and s are 0.

[0243] Formula (4)

[0244] [ka]

[0245] In q, r, and s are 0 or 1, where R 1has the definition given above. Preferably, the sum of the indices q+r+s in formula (4) is 0 or 1. In formula (4), q, r and s are more preferably 0.

[0246] Formula (3)

[0247] [ka]

[0248] In t is, independently in each occurrence, preferably 0 or 1. In formula (3), t is preferably the same and 0.

[0249] In the compounds of formula (2), (2a), (2b) and (2c) or in the preferred compounds of formula (2), (2a), (2b) and (2c), X2 is the same or different in each occurrence and is selected from the group consisting of CH, CR 1 or N, where up to two symbols X2 may be N.

[0250] In the compounds of formula (2), (2a), (2b) and (2c) or in the preferred compounds of formula (2), (2a), (2b) and (2c), X2 is preferably the same or different in each case and is CH, CR 1 or N, where at most one symbol X2 is N.

[0251] In the compounds of formula (2), (2a), (2b) and (2c) or the preferred compounds of formula (2), (2a), (2b) and (2c), X2 is more preferably the same or different in each instance and is CH in two instances and CR in two instances. 1 , or CH in three cases and CR in one case 1 where in each case the substituent R 1 have independently the definitions given above.

[0252] Ar, in each occurrence, is independently an aryl group having 6 to 40 aromatic ring atoms and optionally substituted with one or more R# radicals, or a heteroaryl group having 5 to 40 aromatic ring atoms and optionally substituted with one or more R# radicals; wherein the R# radicals have the definitions given above or preferably below.

[0253] Ar in each occurrence is preferably, independently in each occurrence, an aryl group having 6 to 40 aromatic ring atoms and optionally substituted with one or more R# radicals, or a heteroaryl group having 5 to 40 aromatic ring atoms and containing O or S as heteroatoms and optionally substituted with one or more R# radicals, where the R# radicals have the definitions given above or as preferred.

[0254] Ar in each instance is preferably an aryl group having 6 to 18 carbon atoms, optionally substituted by one or more R# radicals, or dibenzofuranyl or dibenzothiophenyl, optionally substituted by one or more R# radicals, where the R# radicals have the definitions given above or preferably below.

[0255] Ar is more preferably phenyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, 1,3-biphenyl, 1,4-biphenyl, terphenyl, quaterphenyl, naphthyl, fluorenyl, 9,9-diphenylfluorenyl, bispirofluorenyltriphenylenyl, dibenzofuranyl, phenyl-substituted dibenzofuranyl, dibenzothiophenyl, or phenyl-substituted dibenzothiophenyl. Ar is most preferably phenyl, 1,3-biphenyl, 1,4-biphenyl, naphth-2-yl, or triphenyl-2-yl.

[0256] In the compounds of formula (2), (2a), (2b) and (2c) or preferred compounds of formula (2), (2a), (2b) and (2c), R# is in each case the same or different, preferably D, CN, and has 5 to 40 aromatic ring atoms, and in each case one or more R 2 The ring system is selected from the group consisting of aromatic or heteroaromatic ring systems optionally substituted by radicals.

[0257] In the compounds of formula (2), (2a), (2b) and (2c) or preferred compounds of formula (2), (2a), (2b) and (2c), R# is the same or different in each occurrence and is more preferably an unsubstituted aromatic ring system having 5 to 20 aromatic ring atoms, preferably phenyl.

[0258] In a preferred embodiment of the invention, A conforms to formula (4) with the substituents described above or as preferred.

[0259] In a preferred embodiment of the invention, A conforms to formula (3) with the substituents described above or as preferred.

[0260] Compounds of formula (2), (2a), (2b) and (2c) (where A conforms to formula (3) and q, r, s and t are 0) can be converted to compounds of formula (2d) and (2e)

[0261] [ka]

[0262] (wherein X2 and Ar have the preferred definitions given above). It may be expressed as:

[0263] Therefore, the present invention further provides an organic electroluminescent device as described above or as preferred, wherein at least one compound of formula (2) corresponds to a compound of formula (2d) or formula (2e).

[0264] In preferred embodiments of compounds of formula (2), (2a), (2b), (2c), (2d), or (2e), the substituents of formula (3) and (4) are bonded to each other at the 2- or 5-position, respectively, of the indolo[3,2,1-jk]carbazole, as shown in the following schematic form, where the dotted lines indicate the bonds to the substituents of formula (3) and (4):

[0265] [ka]

[0266] Examples of suitable host materials of formulas (2), (2a), (2b), (2c), (2d) and (2e) selected according to the present invention and preferably used in combination with at least one compound of formula (1) in the electroluminescent devices of the present invention are the structures shown in Table 3 below.

[0267] [Table 3-1]

[0268] [Table 3-2]

[0269] [Table 3-3]

[0270] [Table 3-4]

[0271] [Table 3-5]

[0272] [Table 3-6]

[0273] Particularly suitable compounds of formula (2), which are preferably used in combination with at least one compound of formula (1) in the electroluminescent devices of the present invention, are compounds H1 to H21 in Table 4.

[0274] [Table 4-1]

[0275] [Table 4-2]

[0276] Highly suitable compounds of formula (2), which are preferably used in combination with at least one compound of formula (1) in the electroluminescent devices of the present invention, are compounds H1, H3, H4, H5, H6, H7, H8, H11 and H12.

[0277] The preparation of compounds of formula (2) or preferred compounds of formulae (2), (2a), (2b), (2c), (2d), and (2e), as well as the compounds of Table 3 and compounds H1-H21, is known to those skilled in the art. The compounds may be prepared by synthetic steps known to those skilled in the art, such as bromination, Suzuki coupling, Ullmann coupling, Hartwig-Buchwald coupling, etc. A suitable synthetic method is outlined in Scheme 2 below, where the symbols and indices used have the definitions given above.

[0278] [ka]

[0279] The host material of the above-mentioned formula (1) and its preferred embodiments or the compounds of Table 1 and compounds E1 to E54 can be combined, if desired, in the device of the present invention with the host material of the mentioned formulas (2), (2a), (2b), (2c), (2d) and (2e) and its preferred embodiments or the compounds of Table 3 or compounds H1 to H21.

[0280] The present invention also provides a method for preparing a compound of formula (1) as host material 1 and a compound of formula (2) as host material 2.

[0281] [ka]

[0282] (wherein the symbols and subscripts used are as follows: X may be the same or different in each case, and CR 0 or N, where at least one symbol X is N; X2 may be the same or different in each case, CH, CR 1 or N, where up to two symbols X2 may be N; Y and Y1, in each occurrence, are the same or different and are selected from O and S; L, in each occurrence, is the same or different and is a single bond or an aromatic ring system having 6 to 30 aromatic ring atoms; L1, in each occurrence, is the same or different and is a single bond or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms; R in each case 0 are independently H, D, or an unsubstituted or partially or fully deuterated aromatic ring system having 6 to 18 carbon atoms; R* in each occurrence is independently D or an aromatic or heteroaromatic ring system having 6 to 18 carbon atoms, which may be partially or fully deuterated; R# may be the same or different in each case and may be D, F, Cl, Br, I, CN, NO2, C(=O)R 2 , P(=O)(Ar1)2, P(Ar1)2, B(Ar1)2, Si(Ar1)3, Si(R 2 ) 3, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms (each of which may be selected from the group consisting of one or more R 2 radicals) (wherein one or more non-adjacent CH groups are optionally substituted by R 2 C=CR 2 , Si(R 2 )2, C=O, C=S, C=NR 2 , P(=O)(R 2 ), SO, SO2, NR 2 , O, S or CONR 2 and one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO), having 5 to 40 aromatic ring atoms, in each case one or more R 2 Aromatic or heteroaromatic ring systems, optionally substituted by radicals, having 5 to 40 aromatic ring atoms and one or more R 2 an aryloxy or heteroaryloxy group optionally substituted by a radical, or an aryloxy group having 5 to 40 aromatic ring atoms and one or more R 2 an aralkyl or heteroaralkyl group optionally substituted by a radical; R in each occurrence is the same or different and is selected from a CN group, an aromatic ring system having 6 to 40 aromatic ring atoms, and a heteroaromatic ring system having 10 to 40 aromatic ring atoms, wherein the ring system is selected from one or more R 2 optionally substituted by radicals, the heteroaromatic ring system being bonded via N when the heteroaromatic ring system contains a nitrogen atom; R 1are in each occurrence the same or different and are selected from the group consisting of CN, a linear alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms; at the same time, two substituents R attached to the same carbon atom or adjacent carbon atoms 1 but one or more R 2 It is possible to form monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring systems, which may be optionally substituted by radicals; R 2 are the same or different in each case and are H, D, F, Cl, Br, I, CN, NO2, N(Ar1)2, NH2, N(R 3 )2, C(=O)Ar1, C(=O)H, C(=O)R 3 , P(═O)(Ar1)2, a linear alkyl, alkoxy, or thioalkyl group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 carbon atoms, or an alkenyl or alkynyl group having 2 to 40 carbon atoms (each of which may be one or more R 3 radicals) (wherein one or more non-adjacent CH groups are substituted by HC=CH, R 3 C=CR 3 , C≡C, Si(R 3 )2, Ge(R 3 )2, Sn(R 3 )2, C=O, C=S, C=Se, C=NR 3 , P(=O)(R 3 ), SO, SO2, NH, NR 3 , O, S, CONH or CONR 3 and one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO), having 5 to 60 aromatic ring atoms, in each case one or more R3 Aromatic or heteroaromatic ring systems, optionally substituted by radicals, having 5 to 60 aromatic ring atoms and one or more R 3 two or more adjacent substituents R selected from the group consisting of an aryloxy or heteroaryloxy group optionally substituted by a radical, or a combination of these systems; 2 but one or more R 3 optionally capable of forming monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring systems, optionally substituted by radicals; R 3 are in each occurrence the same or different and are selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, or CN, and may be substituted by one or more alkyl groups, each having 1 to 4 carbon atoms; 3 The substituents, taken together, may form a monocyclic or polycyclic aliphatic ring system; Ar1 in each occurrence is the same or different and has 5 to 30 aromatic ring atoms and one or more non-aromatic R 3 at the same time, two Ar radicals attached to the same nitrogen, phosphorus or boron atom are also joined by a single bond or an N(R 3 ), C(R 3 ) 2, may be crosslinked to each other by a bridge selected from O and S; Ar2 and Ar3 in each instance each independently have 5 to 40 aromatic ring atoms and one or more R 2 an aryl or heteroaryl group optionally substituted by a radical; A in each instance is independently represented by formula (3) or (4),

[0283] [ka]

[0284] is the basis of; Ar, in each occurrence, is independently an aryl group having 6 to 40 aromatic ring atoms, optionally substituted with one or more R# radicals, or a heteroaryl group having 5 to 40 aromatic ring atoms, optionally substituted with one or more R# radicals; * indicates the site of attachment to formula (2); a, b, and c at each occurrence are each independently 0 or 1, where the sum of the indices a+b+c at each occurrence is 1; m and o in each occurrence are independently 0, 1, 2, 3, or 4; n and p in each occurrence are each independently 0, 1, 2, or 3; (q, r, s, and t in each case are independently 0 or 1.) Further provided is a mixture comprising:

[0285] The details regarding the host materials of formula (1) and (2) and their preferred embodiments apply correspondingly to the mixtures of the present invention.

[0286] Particularly preferred mixtures of host materials of formula (1) and formula (2) for the devices of the present invention are obtained by combining compounds E1 to E54 with compounds of Table 3.

[0287] Highly preferred mixtures of host materials of formula (1) and formula (2) for the devices of the present invention are obtained by combining compounds E1 to E54 with compounds H1 to H21 as shown in Table 5 below.

[0288] [Table 5-1]

[0289] [Table 5-2]

[0290] Table 5-3

[0291] Table 5-4

[0292] Table 5-5

[0293] Table 5-6

[0294] Table 5-7

[0295] Table 5-8

[0296] Table 5-9

[0297] Table 5-10

[0298] Table 5-11

[0299] The concentration of the electron-transporting host material of formula (1) as described above or as preferred in the inventive mixture or in the light-emitting layer of the inventive device is in the range of 5% to 90% by weight, preferably in the range of 10% to 85% by weight, more preferably in the range of 20% to 85% by weight, even more preferably in the range of 30% to 80% by weight, very especially preferably in the range of 20% to 60% by weight, and most preferably in the range of 30% to 50% by weight, based on the total mixture or based on the total composition of the light-emitting layer.

[0300] The concentration of the hole-transporting host material of formula (2) as described above or as preferred in the inventive mixture or in the light-emitting layer of the inventive device is in the range of 10% to 95% by weight, preferably in the range of 15% to 90% by weight, more preferably in the range of 15% to 80% by weight, even more preferably in the range of 20% to 70% by weight, very especially preferably in the range of 40% to 80% by weight, and most preferably in the range of 50% to 70% by weight, based on the total mixture or based on the total composition of the light-emitting layer.

[0301] The present invention also relates to mixtures which, in addition to the aforementioned host materials 1 and 2, especially mixtures M1 to M1134, as described above or preferably as described above, also contain at least one phosphorescent emitter.

[0302] The present invention also relates to an organic electroluminescent device as described or preferably described above, wherein the light-emitting layer comprises, in addition to the aforementioned host materials 1 and 2, in particular the material combinations M1 to M1134, as described or preferably described above, at least one phosphorescent emitter.

[0303] The term "phosphorescent emitter" typically encompasses compounds which emit light from an excited state with a higher spin multiplicity, i.e., more than one spin state, by a spin-forbidden transition, for example from a triplet state or a state with an even higher spin quantum number, for example a quintet state, which is preferably understood to mean a transition from a triplet state.

[0304] Suitable phosphorescent emitters (= triplet emitters) are especially compounds that emit light, preferably in the visible region, when appropriately excited, and also contain at least one atom with atomic number greater than 20, preferably greater than 38 and less than 84, more preferably greater than 56 and less than 80, especially a metal with this atomic number.Preferred phosphorescent emitters used are compounds that contain copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, especially compounds that contain iridium or platinum.In the context of the present invention, all luminescent compounds that contain the above-mentioned metals are considered to be phosphorescent emitters.

[0305] In general, all phosphorescent complexes as used for phosphorescent OLEDs according to the prior art and known to those skilled in the art of organic electroluminescent devices are suitable.

[0306] Examples of the above-mentioned luminescent materials are disclosed in the applications WO2016 / 015815, WO00 / 70655, WO2001 / 41512, WO2002 / 02714, WO2002 / 15645, EP1191613, EP1191612, EP1191614, WO05 / 033244, WO05 / 019373, US2005 / 0258742, WO2009 / 146770, WO2010 / 015307, WO2010 / 031485, WO2010 / 054731, WO2010 / 054728, WO2010 / 086089, WO2010 / 099852, WO2010 / 102 709, WO2011 / 032626, WO2011 / 066898, WO2011 / 157339, WO2012 / 007086, WO2 014 / 008982, WO2014 / 023377, WO2014 / 094961, WO2014 / 094960, WO2015 / 0360 74, WO2015 / 104045, WO2015 / 117718, WO2016 / 015815, WO2016 / 124304, WO2017 / 032439, WO2015 / 036074, WO2015 / 117718 and WO2016 / 015815.

[0307] A preferred phosphorescent emitter according to the present invention is a compound of formula (III)

[0308] [ka]

[0309] (wherein the symbols and subscripts for this formula (III) are as follows: n+m is 3, n is 1 or 2, and m is 2 or 1; X is N or CR; R is H, D, or a branched or straight chain alkyl group or a partially or fully deuterated branched or straight chain alkyl group. matches.

[0310] Accordingly, the present invention further provides an organic electroluminescent device as described above or as preferred, characterized in that the emissive layer and the host materials 1 and 2 comprise at least one phosphorescent emitter conforming to formula (III) as described above.

[0311] In the emitter of formula (III), n is preferably 1 and m is preferably 2.

[0312] In the emitter of formula (III), preferably one X is selected from N and the other X is CR.

[0313] In the emitter of formula (III), at least one R is preferably different from H. In the emitter of formula (III), preferably two R are different from H and have one of the other definitions given above for the emitter of formula (III).

[0314] Preferred phosphorescent emitters according to the present invention are those of formula (Ia), (IIa) and (IIIa)

[0315] [ka]

[0316] wherein the symbols and subscripts for formulae (Ia), (IIa) and (IIIa) are as follows: R1 is H or D, and R2 is H, D, or a branched or straight chain alkyl group having 1 to 10 carbon atoms, or a partially or fully deuterated branched or straight chain alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 4 to 10 carbon atoms and optionally partially or fully substituted with deuterium. matches.

[0317] Preferred phosphorescent emitters according to the present invention are those of formula (IVa), (Va) and (VIa)

[0318] [ka]

[0319] wherein the symbols and subscripts for formulae (IVa), (Va) and (VIa) are as follows: R1 is H or D, and R2 is H, D, F, or a branched or straight chain alkyl group having 1 to 10 carbon atoms, or a partially or fully deuterated branched or straight chain alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 4 to 10 carbon atoms and optionally partially or fully substituted with deuterium. matches.

[0320] Preferred examples of phosphorescent emitters are shown in Table 6 below.

[0321] [Table 6-1]

[0322] [Table 6-2]

[0323] [Table 6-3]

[0324] [Table 6-4]

[0325] [Table 6-5]

[0326] [Table 6-6]

[0327] Table 6-7

[0328] Table 6-8

[0329] Table 6-9

[0330] Table 6-10

[0331] Table 6-11

[0332] Table 6-12

[0333] Table 6-13

[0334] Table 6-14

[0335] Table 6-15

[0336] Table 6-16

[0337] [Table 6-17]

[0338] [Table 6-18]

[0339] [Table 6-19]

[0340] [Table 6-20]

[0341] Preferred examples of phosphorescent multipod emitters are shown in Table 7 below.

[0342] [Table 7-1]

[0343] [Table 7-2]

[0344] [Table 7-3]

[0345] [Table 7-4]

[0346] In the mixtures of the invention or in the light-emitting layer of the devices of the invention, preference is given to any of the mixtures M1, M2, M3, M4, M5, M6, M7, M8, M9, M10, M11, M12, M13, M14, M15, M16, M17, M18, M19, M20, M21, M22, M23, M24, M25, M26, M27, M28, M29, M30, M31, M32, M33, M34, M35, M36, M37, M38, M39, M40, M41, M42, M43, M44, M45, M46, M47, M48, M49, M50, M51, M52, M53, M54, M 55, M56, M57, M58, M59, M60, M61, M62, M63, M64, M65, M66, M67, M68, M69, M70 , M71, M72, M73, M74, M75, M76, M77, M78, M79, M80, M81, M82, M83, M84, M85, M8 6, M87, M88, M89, M90, M91, M92, M93, M94, M95, M96, M97, M98, M99, M100, M10 1, M102, M103, M104, M105, M106, M107, M108, M109, M110, M111, M112, M113, M 114, M115, M116, M117, M118, M119, M120, M121, M122, M123, M124, M125, M12 6, M127, M128, M129, M130, M131, M132, M133, M134, M135, M136, M137, M138, M139, M140, M141, M142, M143, M144, M145, M146, M147, M148, M149, M150, M1 51, M152, M153, M154, M155, M156, M157, M158, M159, M160, M161, M162, M163, M164, M165, M166, M167, M168, M169, M170, M171, M172, M173, M174, M175, M1 76, M177, M178, M179, M180, M181, M182, M183, M184, M185, M186, M187, M188, M189, M190, M191, M192, M193, M194, M195, M196, M197, M198, M199, M200, M2 01, M202, M203, M204, M205, M206, M207, M208, M209, M210, M211, M212, M213,M214, M215, M216, M217, M218, M219, M220, M221, M222, M223, M224, M225, M226, M227, M228, M229, M230, M231, M232, M233, M234, M235, M236, M237, M238 M239, M240, M241, M242, M243, M244, M245, M246, M247, M248, M249, M250, M251, M252, M253, M254, M255, M256, M257, M258, M259, M260, M261, M262, M263 M264, M265, M266, M267, M268, M269, M270, M271, M272, M273, M274, M275, M276, M277, M278, M279, M280, M281, M282, M283, M284, M285, M286, M287, M288 M289, M290, M291, M292, M293, M294, M295, M296, M297, M298, M299, M300, M301, M302, M303, M304, M305, M306, M307, M308, M309, M310, M311, M312, M313 M314, M315, M316, M317, M318, M319, M320, M321, M322, M323, M324, M325, M326, M327, M328, M329, M330, M331, M332, M333, M334, M335, M336, M337, M338 M339, M340, M341, M342, M343, M344, M345, M346, M347, M348, M349, M350, M351, M352, M353, M354, M355, M356, M357, M358, M359, M360, M361, M362, M363 M364, M365, M366, M367, M368, M369, M370, M371, M372, M373, M374, M375, M376, M377, M378, M379, M380, M381, M382, M383, M384, M385, M386, M387, M388 M389, M390, M391, M392, M393, M394, M395, M396, M397, M398, M399, M400, M401, M402, M403, M404, M405, M406, M407, M408, M409, M410, M411, M412, M413M414、M415、M416、M417、M418、M419、M420、M421、M422、M423、M424、M425、M426、M427、M428、M429、M430、M431、M432、M433、M434、M435、M436、M437、M438、M439、M440、M441、M442、M443、M444、M445、M446、M447、M448、M449、M450、M451、M452、M453、M454、M455、M456、M457、M458、M459、M460、M461、M462、M463、M464、M465、M466、M467、M468、M469、M470、M471、M472、M473、M474、M475、M476、M477、M478、M479、M480、M481、M482、M483、M484、M485、M486、M487、M488、M489、M490、M491、M492、M493、M494、M495、M496、M497、M498、M499、M500、M501、M502、M503、M504、M505、M506、M507、M508、M509、M510、M511、M512、M513、M514、M515、M516、M517、M518、M519、M520、M521、M522、M523、M524、M525、M526、M527、M528、M529、M530、M531、M532、M533、M534、M535、M536、M537、M538、M539、M540、M541、M542、M543、M544、M545、M546、M547、M548、M549、M550、M551、M552、M553、M554、M555、M556、M557、M558、M559、M560、M561、M562、M563、M564、M565、M566、M567、M568、M569、M570、M571、M572、M573、M574、M575、M576、M577、M578、M579、M580、M581、M582、M583、M584、M585、M586、M587、M588、M589、M590、M591、M592、M593、M594、M595、M596、M597、M598、M599、M600、M601、M602、M603、M604、M605、M606、M607、M608、M609、M610、M611、M612、M613、M614, M615, M616, M617, M618, M619, M620, M621, M622, M623, M624, M625, M626, M627, M628, M629, M630, M631, M632, M633, M634, M635, M636, M637, M638 M639, M640, M641, M642, M643, M644, M645, M646, M647, M648, M649, M650, M651, M652, M653, M654, M655, M656, M657, M658, M659, M660, M661, M662, M663 M664, M665, M666, M667, M668, M669, M670, M671, M672, M673, M674, M675, M676, M677, M678, M679, M680, M681, M682, M683, M684, M685, M686, M687, M688 M689, M690, M691, M692, M693, M694, M695, M696, M697, M698, M699, M700, M701, M702, M703, M704, M705, M706, M707, M708, M709, M710, M711, M712, M713 M714, M715, M716, M717, M718, M719, M720, M721, M722, M723, M724, M725, M726, M727, M728, M729, M730, M731, M732, M733, M734, M735, M736, M737, M738 M739, M740, M741, M742, M743, M744, M745, M746, M747, M748, M749, M750, M751, M752, M753, M754, M755, M756, M757, M758, M759, M760, M761, M762, M763 M764, M765, M766, M767, M768, M769, M770, M771, M772, M773, M774, M775, M776, M777, M778, M779, M780, M781, M782, M783, M784, M785, M786, M787, M788 M789、M790、M791、M792、M793、M794、M795、M796、M797、M798、M799、M800、M8 01、M802、M803、M804、M805、M806、M807、M808、M809、M810、M811、M812、M813、M814、M815、M816、M817、M818、M819、M820、M821、M822、M823、M824、M825、M8 26、M827、M828、M829、M830、M831、M832、M833、M834、M835、M836、M837、M838 、M839、M840、M841、M842、M843、M844、M845、M846、M847、M848、M849、M850、M 851、M852、M853、M854、M855、M856、M857、M858、M859、M860、M861、M862、M863 、M864、M865、M866、M867、M868、M869、M870、M871、M872、M873、M874、M875、M 876、M877、M878、M879、M880、M881、M882、M892、M893、M894、M895、M896、M897 M898, M899, M900, M901, M902, M903, M904, M905, M906, M907, M908, M909, M910, M911, M912, M913, M914, M915, M916, M917, M918, M919, M920, M921, M922 M923, M924, M925, M926, M927, M928, M929, M930, M931, M932, M933, M934, M935, M936, M937, M938, M939, M940, M941, M942, M943, M944, M945, M946, M947 M948, M949, M950, M951, M952, M953, M954, M955, M956, M957, M958, M959, M960, M961, M962, M963, M964, M965, M966, M967, M968, M969, M970, M971, M972 M973, M974, M975, M976, M977, M978, M979, M980, M981, M982, M983, M984, M985, M986, M987, M988, M989, M990, M991, M992, M993, M994, M995, M996, M997 、M998、M999、M1000、M1001、M1002、M1003、M1004、M1005、M1006、M1007、M10 08、M1009、M1010、M1011、M1012、M1013、M1014、M1015、M1016、M1017、M1018、M1019, M1020, M1021, M1022, M1023, M1024, M1025, M1026, M1027, M1028, M1 029, M1030, M1031, M1032, M1033, M1034, M1035, M1036, M1037, M1038, M10, 39, M1040, M1041, M1042, M1043, M1044, M1045, M1046, M1047, M1048, M1049, M1050, M1051, M1052 , M1053, M1054, M1055, M1056, M1057, M1058, M1059, M1060, M1061, M1062, M1063, M1064, M1065, M1 066, M1067, M1068, M1069, M1070, M1071, M1072, M1073, M1074, M1075, M1076, M1077, M1078, M1079 , M1080, M1081, M1082, M1083, M1084, M1085, M1086, M1087, M1088, M1089, M1090, M1091, M1092, M1 093, M1094, M1095, M1096, M1097, M1098, M1099, M1100, M1101, M1102, M1103, M1104, M1105, M110 6, M1107, M1108, M1109, M1110, M1111, M1112, M1113, M1114, M1115, M1116, M1117, M1118, M1119, M and / or M1120, M1121, M1122, M1123, M1124, M1125, M1126, M1127, M1128, M1129, M1130, M1131, M1132, M1133, M1134 with a compound of formula (III), (Ia), (IIa), (IIIa), (IVa), (Va), (VIa) or a compound of Table 6 or 7.

[0347] The light-emitting layer in the organic electroluminescent device of the present invention, which comprises at least one phosphorescent emitter, is preferably an infrared-emitting or yellow, orange, red, green, blue or ultraviolet light-emitting layer, more preferably a yellow or green light-emitting layer, and most preferably a green light-emitting layer.

[0348] A yellow-emitting layer is understood here to mean a layer having a photoluminescence maximum in the range of 540 to 570 nm. An orange-emitting layer is understood here to mean a layer having a photoluminescence maximum in the range of 570 to 600 nm. A red-emitting layer is understood here to mean a layer having a photoluminescence maximum in the range of 600 to 750 nm. A green-emitting layer is understood here to mean a layer having a photoluminescence maximum in the range of 490 to 540 nm. A blue-emitting layer is understood here to mean a layer having a photoluminescence maximum in the range of 440 to 490 nm. The photoluminescence maximum of a layer is determined here by measuring the photoluminescence spectrum of a layer having a layer thickness of 50 nm at room temperature, said layer comprising the inventive combination of host materials of formulae (1) and (2) and a suitable emitter.

[0349] The photoluminescence spectrum of the layer is recorded, for example, using a commercially available photoluminescence spectrometer.

[0350] The photoluminescence spectrum of the selected emitter is generally -5 Measurements are made in an oxygen-free solution of 100 moles per mole at room temperature. Suitable solvents are any in which the selected emitter dissolves at the stated concentration. Particularly suitable solvents are typically toluene or 2-methyl-THF, although dichloromethane is also suitable. Measurements are performed using a commercially available photoluminescence spectrometer. The triplet energy T1 in eV is determined from the photoluminescence spectrum of the emitter. First, the peak maximum P1max. (in nm) of the photoluminescence spectrum is determined. The peak maximum P1max. (in nm) is then converted to eV by E(T1 in eV) = 1240 / E(T1 in nm) = 1240 / PLmax. (in nm).

[0351] Thus, preferred phosphorescent emitters are preferably infrared emitters of formula (III), (Ia), (IIa), (IIIa), (IVa), (Va), (VIa) or from Table 6 or 7, the triplet energy T1 of which is preferably from about 1.9 eV to about 1.0 eV.

[0352] Thus, preferred phosphorescent emitters are preferably red emitters of formula (III), (Ia), (IIa), (IIIa), (IVa), (Va), (VIa) or from Table 6 or 7, whose triplet energy T1 is preferably from about 2.1 eV to about 1.9 eV.

[0353] Thus, preferred phosphorescent emitters are preferably yellow emitters of formula (III), (Ia), (IIa), (IIIa), (IVa), (Va), (VIa) or from Table 6 or 7, whose triplet energy T1 is preferably from about 2.3 eV to about 2.1 eV.

[0354] Thus, preferred phosphorescent emitters are preferably green emitters of formula (III), (Ia), (IIa), (IIIa), (IVa), (Va), (VIa) or from Table 6 or 7, the triplet energy T1 of which is preferably from about 2.5 eV to about 2.3 eV.

[0355] Thus, preferred phosphorescent emitters are preferably blue emitters of formula (III), (Ia), (IIa), (IIIa), (IVa), (Va), (VIa) or from Table 6 or 7, the triplet energy T1 of which is preferably from about 3.1 eV to about 2.5 eV.

[0356] Thus, preferred phosphorescent emitters are ultraviolet emitters of formula (III), (Ia), (IIa), (IIIa), (IVa), (Va), (VIa) or from Table 6 or 7, the triplet energy T1 of which is preferably from about 4.0 eV to about 3.1 eV.

[0357] Therefore, particularly preferred phosphorescent emitters are green or yellow emitters as described above, preferably of formula (III), (Ia), (IIa), (IIIa), (IVa), (Va), (VIa), or from Table 6 or 7.

[0358] Very particularly preferred phosphorescent emitters are therefore green emitters, preferably of formula (III), (Ia), (IIa), (IIIa), (IVa), (Va), (VIa) or from Table 6 or 7, whose triplet energy T1 is preferably between about 2.5 eV and about 2.3 eV.

[0359] Most preferably, a green emitter as described above, preferably of formula (III), (Ia), (IIa), (IIIa), (IVa), (Va), (VIa), or from Table 6 or 7, is selected for the composition of the present invention or the light-emitting layer of the present invention.

[0360] Fluorescent emitters can also be present in the light-emitting layer of the devices of the present invention.

[0361] Preferred fluorescent emitters are selected from the arylamine class. In the context of the present invention, arylamine or aromatic amine is understood to mean a compound containing three substituted or unsubstituted aromatic or heteroaromatic ring systems directly bonded to the nitrogen. Preferably, at least one of these aromatic or heteroaromatic ring systems is a fused ring system, more preferably having at least 14 aromatic ring atoms. Preferred examples of these are aromatic anthracenamines, aromatic anthracenediamines, aromatic pyrenamines, aromatic pyrenediamines, aromatic chrysenamines, and aromatic chrysenediamines. Aromatic anthracenamines are understood to mean compounds in which a diarylamino group is directly bonded to an anthracene group, preferably at the 9-position. Aromatic anthracenediamines are understood to mean compounds in which two diarylamino groups are directly bonded to an anthracene group, preferably at the 9- and 10-positions. Aromatic pyrenamines, pyrenediamines, chrysenamines, and chrysenediamines are similarly defined, in which the diarylamino group is bonded to the pyrene, preferably at the 1- or 1- and 6-positions. Further preferred fluorescent emitters are indenofluorene amines or diamines, for example according to WO 2006 / 108497 or WO 2006 / 122630, benzoindenofluorene amines or diamines, for example according to WO 2008 / 006449, and dibenzoindenofluorene amines or diamines, for example according to WO 2007 / 140847, as well as indenofluorene derivatives with fused aryl groups as disclosed in WO 2010 / 012328.

[0362] In a further preferred embodiment of the present invention, at least one emitting layer of the organic electroluminescent device and the host materials 1 and 2 as described above or as preferred may comprise additional host or matrix materials, which is called a mixed matrix system. The mixed matrix system preferably comprises three or four different matrix materials, more preferably three different matrix materials (in other words, in addition to the host materials 1 and 2 as described above, one additional matrix component). Particularly suitable matrix materials that can be used in combination as matrix components of the mixed matrix system are selected from wide bandgap materials, bipolar host materials, electron transport materials (ETMs) and hole transport materials (HTMs).

[0363] Wide bandgap materials are understood herein to mean materials within the scope of the disclosure of US 7,294,849 that are characterized by a bandgap of at least 3.5 eV, where bandgap is understood to mean the gap between the HOMO and LUMO energies of the material.

[0364] In one embodiment of the present invention, the mixture does not contain any additional components, i.e., functional materials, in addition to the components of the electron-transporting host material of Formula (1) and the hole-transporting host material of Formula (2). These mixtures are material mixtures that are used by themselves to produce an emitting layer. These mixtures are used as the only material source in the deposition of the host material for the emitting layer, and are also called premixed systems with a fixed mixing ratio in the deposition. This makes it possible to deposit a layer with a uniform distribution of components in a simple and rapid manner without requiring the precise operation of multiple material sources.

[0365] In another embodiment of the present invention, the mixture also contains a phosphorescent emitter as described above in addition to the electron-transporting host material of formula (1) and the hole-transporting host material of formula (2). In the case of a suitable mixing ratio in vapor deposition, this mixture may also be used as the sole material source as described above.

[0366] Therefore, the components or constituents of the light-emitting layer of the device of the present invention can be processed by vapor deposition or from a solution. The combination of the host materials 1 and 2 described above or as preferred, and optionally the phosphorescent emitter described above or as preferred, is provided for the purpose in a formulation containing at least one solvent. These formulations can be, for example, a solution, a dispersion, or an emulsion. For this purpose, it may be preferable to use a mixture of two or more solvents.

[0367] The present invention therefore further provides a formulation comprising a phosphorescent emitter as described above or as preferred, and an inventive mixture of host materials 1 and 2 as described above, optionally in combination with at least one solvent.

[0368] Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, α-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone ... Hexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indan, methyl benzoate, 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, 1,1-bis(3,4-dimethylphenyl)ethane, hexamethylindan, or a mixture of these solvents.

[0369] The formulation may also comprise at least one further organic or inorganic compound, especially a light-emitting compound, especially a further light-emitting compound and / or a further matrix material, which are also used in the light-emitting layer of the device of the invention.

[0370] The light-emitting layer in the device of the present invention according to the preferred embodiment and light-emitting compound preferably contains 99.9% to 1% by volume, more preferably 99% to 10% by volume, particularly preferably 98% to 60% by volume, and very particularly preferably 97% to 80% by volume of a matrix material consisting of at least one compound of formula (1) according to the preferred embodiment and at least one compound of formula (2) based on the total composition of the light-emitting material and the matrix material. Correspondingly, the light-emitting layer in the device of the present invention preferably contains 0.1% to 99% by volume, more preferably 1% to 90% by volume, more preferably 2% to 40% by volume, and most preferably 3% to 20% by volume of the light-emitting layer consisting of the light-emitting material and the matrix material. When the compound is processed from solution, it is preferable to use the corresponding amount in weight percent rather than the amount specified above in volume percent.

[0371] The light-emitting layer in the device of the present invention according to the preferred embodiment and light-emitting compound preferably contains the matrix material of formula (1) and the matrix material of formula (2) in a volume ratio of 3:1 to 1:3, preferably 1:2.5 to 1:1, more preferably 1:2 to 1:1. When the compounds are processed from solution, it is preferable to use the corresponding ratios in weight percent rather than the ratios specified above in volume percent.

[0372] The arrangement of layers in the organic electroluminescent device of the present invention is preferably as follows: Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode.

[0373] This layer arrangement is the preferred arrangement.

[0374] At the same time, it should again be pointed out that not all of the layers mentioned need be present and / or further layers may additionally be present.

[0375] The organic electroluminescent device of the present invention may contain two or more emitting layers. At least one of the emitting layers is the emitting layer of the present invention, which contains at least one compound of formula (1) as host material 1 and at least one compound of formula (2) as host material 2 as described above. More preferably, these emitting layers have several emission maxima between 380 nm and 750 nm, and produce white light as a whole; in other words, various emitting compounds that can emit fluorescence or phosphorescence and emit blue, yellow, orange, or red light are used in the emitting layers. Particularly preferred is a three-layer system, i.e., a system with three emitting layers, where the three layers emit blue, green, and orange or red light (for a basic configuration, see, for example, WO2005 / 011013). It should be noted that, for the generation of white light, it may be preferable to use individual emitting compounds that emit light over a wide wavelength range, rather than multiple colored emitting compounds.

[0376] Suitable charge transporting materials that can be used in the hole-injecting or hole-transporting layer or electron-blocking layer or in the electron-transporting layer of the organic electroluminescent device of the present invention are, for example, the compounds disclosed in Y. Shirota et al., Chem. Rev. 2007, 107(4), 953-1010, or other materials that are used in these layers according to the prior art.

[0377] The material used in the electron transport layer may be any material that has been used in the prior art as an electron transport material in an electron transport layer. Particularly preferred are aluminum complexes such as Alq3, zirconium complexes such as Zrq4, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, oxadiazole derivatives, aromatic ketones, lactams, boranes, diazaphosphole derivatives, and phosphine oxide derivatives. Further preferred materials are derivatives of the aforementioned compounds, as disclosed in JP2000 / 053957, WO2003 / 060956, WO2004 / 028217, WO2004 / 080975, and WO2010 / 072300.

[0378] Preferred hole transport materials are, inter alia, materials which can be used in hole transport, hole injection or electron blocking layers, such as indenofluorene amine derivatives (for example according to WO 06 / 122630 or WO 06 / 100896), the amine derivatives disclosed in EP 1 661 888, hexaazatriphenylene derivatives (for example according to WO 01 / 049806), amine derivatives with condensed aromatic systems (for example according to US 5,061,569), the amine derivatives disclosed in WO 95 / 09147, monobenzoindenofluorene amines (for example according to WO 08 / 006449), dibenzoindenofluoreneamines (for example according to WO 07 / 140847), spirobifluoreneamines (for example according to WO 2012 / 034627 or unpublished EP 12000929.5), fluoreneamines (for example according to WO 2014 / 015937, WO 2014 / 015938 and WO 2014 / 015935), spirodibenzopyranamines (for example according to WO 2013 / 083216), and dihydroacridine derivatives (for example WO 2012 / 150001).

[0379] A suitable cathode for the device of the present invention is a metal, metal alloy, or multilayer structure composed of various metals, such as alkaline earth metals, alkali metals, main group metals, or lanthanides (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.), having a low work function. Additionally, alloys composed of alkali metals or alkaline earth metals and silver, such as alloys composed of magnesium and silver, are also suitable. In the case of multilayer structures, in addition to the metals mentioned, additional metals with relatively high work functions, such as Ag or Al, can also be used. In this case, metal combinations such as Ca / Ag, Mg / Ag, or Ba / Ag are commonly used. It may be preferable to introduce a thin intermediate layer of a material with a high dielectric constant between the metallic cathode and the organic semiconductor. Examples of materials useful for this purpose are alkali metal or alkaline earth metal fluorides, but also the corresponding oxides or carbonates (e.g., LiF, Li2O, BaF2, MgO, NaF, CsF, Cs2CO3, etc.). Lithium quinolinate (LiQ) can also be used for this purpose. The thickness of this layer is preferably 0.5 to 5 nm.

[0380] Preferred anodes are materials with a high work function. Preferably, the anode has a work function greater than 4.5 eV vs. vacuum. First, metals with high redox potentials are suitable for this purpose, such as Ag, Pt, or Au. Second, metal / metal oxide electrodes (e.g., Al / Ni / NiO x , Al / PtO x) may be preferred. Depending on the application, at least one of the electrodes must be transparent or partially transparent to allow irradiation of the organic material (organic solar cells) or emission of light (OLEDs, O-lasers). Preferred anode materials here are conductive mixed metal oxides. Indium tin oxide (ITO) or indium zinc oxide (IZO) are particularly preferred. Furthermore, conductive doped organic materials, especially conductive doped polymers, are preferred. In addition, the anode may also consist of two or more layers, for example an inner layer of ITO and an outer layer of a metal oxide, preferably tungsten oxide, molybdenum oxide or vanadium oxide.

[0381] During the manufacturing process, the organic electroluminescent device of the present invention is appropriately structured (depending on the application), contacts are connected, and finally sealed, since the lifetime of the device of the present invention is shortened in the presence of water and / or air.

[0382] The fabrication of the device of the present invention is not limited thereto. One or more organic layers, including the light-emitting layer, can be coated by sublimation. In this case, the material is evaporated in a vacuum sublimation system at 1000 K. -5 less than mbar, preferably 10 -6 It is applied by evaporation at an initial pressure of less than 10 mbar, but in this case the initial pressure can be lowered further, for example to 10 -7 It is also possible to have a pressure below mbar.

[0383] The organic electroluminescent device of the present invention is preferably characterized in that one or more layers are coated by the OVPD (organic vapor phase deposition) method or with the aid of carrier gas sublimation. In this case, the material is -5 It is applied at a pressure of between mbar and 1 bar. A special case of this method is the OVJP (organic vapor jet printing) method, in which the material is applied directly by a nozzle and is therefore structured (for example, MS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).

[0384] The organic electroluminescent device of the present invention is further preferably characterized in that one or more organic layers comprising the composition of the present invention are produced from solution, for example by spin coating, or by any printing method, for example, screen printing, flexographic printing, nozzle printing or offset printing, but more preferably LITI (light-induced thermal imaging, thermal transfer printing) or inkjet printing.For this purpose, suitable host materials 1 and 2 and a phosphorescent emitter are required.Processing from solution has the advantage that, for example, the emitting layer can be applied in a very simple and inexpensive way.This technique is particularly suitable for mass production of organic electroluminescent devices.

[0385] In addition, hybrid methods are possible, in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapor deposition.

[0386] These methods are known in general terms to those skilled in the art and are applicable to organic electroluminescent devices.

[0387] The present invention therefore further provides a method for producing an organic electroluminescent device according to the invention as described above or as preferred, characterized in that the light-emitting layer is applied by vapor deposition, in particular by sublimation, and / or by OVPD (organic vapor phase deposition) and / or with the aid of carrier gas sublimation, or from solution, in particular by spin-coating or printing.

[0388] In the case of production by vapor deposition, there are two principal ways in which the light-emitting layer of the present invention can be applied or deposited on any substrate or previous layer. First, the materials used can be initially charged into respective material sources and finally evaporated from different material sources ("co-evaporation"). Second, various materials can be premixed (premixed system), and the mixture can be initially charged into a single material source from which it will finally be evaporated ("premix evaporation"). In this way, it is possible to achieve the deposition of a light-emitting layer with a uniform distribution of components in a simple and rapid manner, without requiring the precise operation of multiple material sources.

[0389] The present invention therefore further provides a method for the preparation of a device according to the invention, characterized in that at least one compound of formula (1) as described above or as described as preferred and at least one compound of formula (2) as described above or as described as preferred, optionally together with at least one phosphorescent emitter as described above or as described as preferred, are deposited successively or simultaneously from the gas phase from at least two material sources to form an emissive layer.

[0390] In a preferred embodiment of the invention, the light-emitting layer is applied using vapor deposition, where the components of the composition are premixed and evaporated from a single material source.

[0391] Accordingly, the present invention further provides a method for producing a device of the present invention, characterized in that at least one compound of formula (1) and at least one compound of formula (2) together with at least one phosphorescent emitter are deposited sequentially or simultaneously from the gas phase as a mixture to form an emissive layer.

[0392] The present invention further provides a method for producing a device of the present invention as described above or as described as preferred, characterized in that at least one compound of formula (1) and at least one compound of formula (2) as described above or as described as preferred are applied from solution together with at least one phosphorescent emitter to form an emissive layer.

[0393] The device of the present invention is characterized by the following surprising advantages over the prior art: As described above, the use of the described material combinations of host materials 1 and 2, among other things, improves the lifetime of the device.

[0394] However, as will be seen in the examples presented below, by comparison of data for OLEDs with combinations from the prior art, it is possible to determine that the inventive combination of matrix materials in the EML leads to devices with lifetimes increased by approximately 19% to 65%, independent of the emitter concentration.

[0395] It should be pointed out that variations of the embodiments described in the present invention are included within the scope of the present invention. Any feature disclosed in the present invention may be replaced with an alternative feature serving the same purpose or an equivalent or similar purpose, unless it is expressly excluded. Therefore, any feature disclosed in the present invention should be considered as an example from a generic series, or as an equivalent or similar feature, unless otherwise specified.

[0396] All features of the present invention may be combined with one another in any way, unless certain features and / or steps are mutually exclusive. This is particularly true of preferred features of the present invention. Similarly, features of non-essential combinations may be used individually (and not in combination).

[0397] The technical teachings disclosed along with the present invention may be extracted and combined with other examples.

[0398] The present invention is further illustrated by the examples that follow, but are not intended to limit the invention thereby.

[0399] General methods : The Gaussian16 (Rev. B.01) software package is used for all quantum chemical calculations. The neutral singlet ground state is optimized at the B3LYP / 6-31G(d) level. The HOMO and LUMO values ​​are determined at the B3LYP / 6-31G(d) level from the B3LYP / 6-31G(d)-optimized ground state energy. TD-DFT singlet and triplet excitations (vertical excitations) are calculated by the same method (B3LYP / 6-31G(d)) and optimized ground state geometries. Standard settings for SCF and gradient convergence are used.

[0400] From the energy calculations, the HOMO is obtained as the last orbital occupied by two electrons (alpha occ. eigenvalue) and the LUMO as the first unoccupied orbital (alpha virt. eigenvalue) in Hartree units (HEh and LEh), where Heh and LEh represent the HOMO energy in Hartree units and the LUMO energy in Hartree units, respectively. Using this, the HOMO and LUMO values ​​calibrated by cyclic voltammetry measurements are determined as follows in electron volts: HOMOcorr=0.90603*HOMO-0.84836; LUMOcorr=0.99687*LUMO-0.72445 The triplet level T1 of a material is defined as the relative excitation energy (in eV) of the triplet state with the lowest energy found by quantum chemical energy calculation.

[0401] The singlet level S1 of a material is defined as the relative excitation energy (in eV) of the second lowest energy singlet state found by quantum chemical energy calculations.

[0402] The lowest energetic singlet state is called S0.

[0403] The method described herein is independent of the software package used and always gives the same results. Examples of programs frequently used for this purpose are "Gaussian 09" (Gaussian Inc.) and Q-Chem 4.1 (Q-Chem, Inc.). In the present case, energies are calculated using the software package "Gaussian 16, Rev. B.01."

[0404] Example 1 OLED manufacturing The examples that follow (see Tables 8-10) demonstrate the use of material combinations of the present invention in OLEDs as compared to prior art material combinations.

[0405] Pretreatment for Examples V1-V5 and E1a-E5g: Glass plates coated with 50 nm thick structured ITO (indium tin oxide) are treated first with oxygen plasma and then with argon plasma before coating. These plasma-treated glass plates form the substrates onto which the OLEDs are applied.

[0406] The OLED basically has the following layer structure: substrate / hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / emissive layer (EML) / optional hole blocking layer (HBL) / electron transport layer (ETL) / optional electron injection layer (EIL), and finally a cathode. The cathode is formed by a 100 nm thick aluminum layer. The exact structure of the OLED can be found in Table 8. Unless already mentioned above, the materials required for the fabrication of the OLED are listed in Table 10. The device data for the OLED is listed in Table 9.

[0407] Examples V1 and V5 are comparative examples containing a biscarbazole as a hole-transporting host according to the prior art.

[0408] Examples E1a-E5f show data for OLEDs of the present invention.

[0409] All materials are applied by thermal evaporation in a vacuum chamber. In this case, the light-emitting layer always consists of at least two matrix materials and a light-emitting dopant (emitter) that is added to the matrix materials by co-evaporation in a specific volumetric proportion. A specification such as E13:BCbz1:TE2 (32%:60%:8%) means that the layer contains 32% by volume of material E13, 60% by volume of BCbz1, and 8% by volume of TE2. Similarly, the electron-transporting layer may also consist of a mixture of two materials.

[0410] Electroluminescence spectrum of 1000 cd / m 2 The luminance is determined at 10 mA / cm and the CIE 1931 x and y color coordinates are calculated from it. 2 SE10 and EQE10 refer to the voltage required for a current density of 10 mA / cm. 2 The power efficiency and external quantum efficiency achieved by the

[0411] Lifetime LT is forward cd / m 2 The L1=80% figure in Table 9 indicates that the lifetime reported in the LT column is in cd / m 2 This means that the time it takes for the brightness, expressed as

[0412] Use of the mixtures of the present invention in OLEDs Combinations of materials of the present invention are used as matrix materials in the emissive layers of green phosphorescent OLEDs in Examples E1a-k, E2a-h, E3a-g, E4a-j, and E5a-g. For comparison with the prior art, materials E7, E8, E13, E15, E18, and BCbz1-BCbz5 are used in Examples V1-V5. Comparing the inventive examples with the corresponding comparative examples, it is clear that each of the inventive examples exhibits a clear advantage in device lifetime over the performance data of other comparable OLEDs.

[0413] Table 8-1

[0414] Table 8-2

[0415] Table 8-3

[0416] Table 8-4

[0417] Table 8-5

[0418] Table 9-1

[0419] Table 9-2

[0420] Table 10-1

[0421] Table 10-2

[0422] Table 10-3

[0423] The following syntheses are carried out in dry solvents under a protective gas atmosphere unless otherwise specified. Solvents and reagents can be purchased, for example, from Sigma-ALDRICH or ABCR. The respective numbers in square brackets or the numbers cited for individual compounds refer to the CAS numbers of compounds known from the literature.

[0424] S1a:

[0425] [ka]

[0426] 2-(8-chlorodibenzofuran-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [2140871-51-6] (32.86 g, 100.0 mmol), 2-chloro-4-dibenzofuran-3-yl-6-phenyl-1,3,5-triazine [2142681-84-1] (37.57 g, 105.0 mmol), and sodium carbonate (22.26 g, 210.0 mmol) were suspended in 600 ml of ethylene glycol dimethyl ether and 300 ml of water and inactivated for 30 minutes. Then, tri-o-tolylphosphine (913 mg, 3.0 mmol) and palladium(II) acetate (112 mg, 0.5 mmol) were added, and the reaction mixture was heated under reflux for 20 hours. After cooling, the precipitated solid was filtered off with suction and washed with ethanol. The crude product is recrystallized from m-xylene. Yield: 46.11 g (88 mmol, 88%) solid, 98% by HPLC.

[0427] Similarly, the following compounds can be prepared: Purification can be carried out using column chromatography or recrystallization can be carried out using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydro-furan, n-butyl acetate, 1,4-dioxane, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and the like.

[0428] [Table 11-1]

[0429] [Table 11-2]

[0430] S1b:

[0431] [ka]

[0432] S1a (46.11 g, 88.0 mmol), bis(pinarato)diboron [73183-34-3] (25.39 g, 100.0 mmol), and potassium acetate (28.82 g, 293.6 mmol) in 4-dioxane (700 ml) are first charged and inerted with argon for 2 minutes. XPhos [564483-18-7] (456 mg, 0.96 mmol) and Pd2(dba)3 [51364-51-3] (435 mg, 0.48 mmol) are then added, and the reaction mixture is stirred under reflux for 26 hours. After cooling, the solvent is removed by rotary evaporation, and the residue is worked up by extraction with toluene / water. The organic phase is dried over Na2SO4 and concentrated to dryness by rotary evaporation. The residue is boiled under reflux with ethyl acetate for 2 hours, and the solid is filtered off with suction and washed with ethyl acetate. Yield: 49.4 g (80.2 mmol, 91%) solid; 1 97% by H NMR.

[0433] Similarly, the following compounds can be prepared: Instead of X-Phos, S-Phos or tricyclohexylphosphine can be used as a ligand, or Pd(dppf)Cl2xCH2Cl2 [95464-05-4] can be used for the boronation reaction of functional bromide groups. Purification can be carried out using column chromatography, or recrystallization can be carried out using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-dioxane, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.

[0434] [Table 12-1]

[0435] [Table 12-2]

[0436] [Table 12-3]

[0437] S1c:

[0438] [ka]

[0439] Under an inert atmosphere, 2-bromo-7-chlorodibenzofuran [CAS-2355229-03-5] (28.15 g, 100 mmol), 2-phenyl-9H-carbazole [88590-00-5] (25.54 g, 105 mmol), and sodium tert-butoxide (19.21 g, 200 mmol) were first charged to 1000 mL of ortho-xylene. Then, tri-tert-butylphosphine [13716-12-6] (1 mol / L solution in toluene, 5.0 mL, 5.0 mmol) and tris(dibenzylideneacetone)dipalladium [51364-51-3] (1.14 g, 1.25 mmol) were added alternately, and the reaction mixture was heated under reflux for 16 hours. The reaction mixture was cooled to room temperature and worked up by extraction with toluene / water. The organic phases are combined, dried over Na2SO4 and the solvent is removed under reduced pressure on a rotary evaporator. The solid obtained is suspended in 300 ml of ethanol, stirred under reflux for 1 hour and filtered off with suction. The crude product is recrystallized from ethyl acetate. Yield: 28.4 g (64 mmol, 48%) of a solid. 1 98% by H NMR.

[0440] Similarly, the following compounds can be prepared: Purification can be carried out using column chromatography or recrystallization can be carried out using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydro-furan, n-butyl acetate, 1,4-dioxane, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and the like.

[0441] [Table 13]

[0442] S1d:

[0443] [ka]

[0444] Under an inert atmosphere, 1-bromo-8-iododibenzofuran [1822311-11-4] (37.28 g, 100 mmol), 3-phenyl-9H-carbazole [103012-26-6] (16.71 g, 100 mmol), potassium carbonate (34.55 g, 250 mmol), copper iodide (3.81 g, 20.0 mmol), and 1,3-di(2-pyridinyl)propane-1,3-dione (4.52 g, 20.0 mmol) in a first charge of DMF (350 ml) was inerted with argon for an additional 15 minutes and then stirred at 115° C. for 32 hours. The mixture was allowed to cool to room temperature, filtered through a Celite bed, washed twice with 200 ml of DMF, and the filtrate was concentrated to dryness on a rotary evaporator. The residue is worked up by extraction with dichloromethane / water, the organic phase is washed twice with water, saturated NaCl solution once and dried over Na2SO4. 150 ml of ethanol is added, the dichloromethane is extracted on a rotary evaporator up to 500 mbar, the precipitated solid is filtered off with suction and washed with ethanol. Yield: 24.71 g (50.6 mmol, 51%) of solid; 1 95% by H NMR.

[0445] Similarly, the following compounds can be prepared: Purification can be carried out using column chromatography or recrystallization can be carried out using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydro-furan, n-butyl acetate, 1,4-dioxane, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and the like.

[0446] [Table 14]

[0447] S1e:

[0448] [ka]

[0449] To the initially charged 8-bromodibenzofuran-1-yl-trifluoromethanesulfonate [2247123-46-0] (47.00 g, 118.9 mmol), 4,4,5,5-tetramethyl-2-(2-triphenylphenyl)-1,3,2-dioxaborolane (490.72 g, 140.4 mmol), and K2CO3 (32.88 g, 237.9 mmol) in a flask, toluene (500 ml) and water (150 ml) were added, and the mixture was inerted with argon for 30 minutes. Then, Pd2(dba)3 (545 mg, 0.59 mmol) and tri-o-tolylphosphine [6163-58-2] (724 mg, 2.38 mmol) were added, and the mixture was heated under reflux for 24 hours. After cooling, the precipitated solid was filtered off with suction and washed twice with ethanol. The crude product is extracted in ethanol by stirring under reflux for 2 hours, and the solid is filtered off with suction after cooling. Yield: 58.8 g (108 mmol, 91%) of solid; 1 98% purity by H NMR.

[0450] Similarly, the following compounds can be prepared: Purification can be carried out using column chromatography or recrystallization can be carried out using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydro-furan, n-butyl acetate, 1,4-dioxane, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and the like.

[0451] [Table 15-1]

[0452] [Table 15-2]

[0453] [Table 15-3]

[0454] Preparation of compounds Synthesis of E1:

[0455] [ka]

[0456] To the initially charged 2,4-diphenyl-6-[8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-dibenzofuranyl]-1,3,5-triazine [2138490-96-5] (15.31 g, 29.1 mmol), S1e (15.06 g, 27.8 mmol), and K3PO4 (12.17 g, 57.3 mmol) in a flask, tetrahydrofuran (200 ml) and water (50 ml) were added, and the mixture was inerted with argon for 30 minutes. Then, Pd(OAc)2 (124 mg, 0.55 mmol) and XPhos [564483-18-7] (556 mg, 1.11 mmol) were added, and the mixture was heated under reflux for 24 hours. After cooling, the precipitated solid is filtered off with suction, washed twice with water and twice with ethanol. The crude product is subjected to three hot extractions with toluene / heptane (1:1), then recrystallized three times from toluene, and finally sublimed under high vacuum. Yield: 14.8 g (18.7 mmol, 67%) of solid; Purity: >99.9% by HPLC.

[0457] Similarly, the following compounds can be prepared: The catalyst system (palladium source and ligand) used here can be Pd2(dba)3 and SPhos [657408-07-6] or bis(triphenylphosphine)palladium(II) chloride [13965-03-2]. Purification can be carried out using column chromatography, or recrystallization or hot extraction can be carried out using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, and 1,4-dioxane. Recrystallization can be carried out using high-boiling solvents such as dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0458] [Table 16-1]

[0459] [Table 16-2]

[0460] [Table 16-3]

[0461] [Table 16-4]

[0462] [Table 16-5]

[0463] [Table 16-6]

[0464] [Table 16-7]

[0465] [Table 16-8]

[0466] E20:

[0467] [ka]

[0468] To the initially charged 2,4-diphenyl-6-[8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-dibenzofuranyl]-1,3,5-triazine [2138490-96-5] (15.31 g, 29.1 mmol), S1d (14.41 g, 29.5 mmol), and Na2CO3 (6.17 g, 58.2 mmol) in a flask, toluene (300 ml) and water (100 ml) were added, and the mixture was inerted with argon for 30 minutes. Tetrakis(triphenylphosphine)palladium(0) [14221-01-3] (1.00 g, 0.87 mmol) was then added, and the mixture was heated under reflux for 36 hours. After cooling, the reaction mixture is worked up by extraction with toluene and water, the combined organic phases are dried over Na2SO4, and the filtrate is concentrated to dryness on a rotary evaporator. The residue is suspended in 350 ml of hot EtOH and stirred under reflux for 1 h. After cooling, the solid is filtered off with suction. The crude product is subjected to two hot extractions with toluene / heptane (1:1), then recrystallized three times from n-butyl acetate, and finally sublimed under high vacuum. Yield: 14.8 g (18.7 mmol, 67%) of solid; purity: >99.9% by HPLC.

[0469] Similarly, the following compounds can be prepared: The catalyst system used here can be Pd2(dba)3 and SPhos [657408-07-6] (palladium source and ligand) or bis(triphenylphosphine)palladium(II) chloride [13965-03-2] instead of tetrakis(triphenylphosphine)palladium(0). Purification can be carried out using column chromatography, or recrystallization or hot extraction can be carried out using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, and 1,4-dioxane. Recrystallization can be carried out using high-boiling solvents such as dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0470] [Table 17-1]

[0471] [Table 17-2]

[0472] [Table 17-3]

[0473] H3:

[0474] [ka]

[0475] The initially charged 9-[1,1'-biphenyl]-3-yl-3-bromo-9H-carbazole (59.88 g, 150.3 mmol) [CAS-1428551-28-3], 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane- To 2-ylindolo[3,2,1-jk]carbazole (51.1 g, 147.3 mmol) [CAS-1454807-26-1], K3PO4 (95.7 g, 451 mmol), tri(ortho-tolyl)phosphine (2.33 g, 7.52 mmol), and Pd(OAc)2 (840 mg, 3.76 mmol) were added, and the mixture was stirred under reflux for 32 h. After cooling, the mixture was worked up by extraction with toluene and water. The aqueous phase was extracted three times with toluene (500 ml each time), and the combined organic phases were dried over Na2SO4. The crude product was first extracted by stirring in EtOH (1500 ml). The solid was filtered off with suction, subjected to two hot extractions with heptane / toluene, recrystallized twice from DMAc, and finally sublimed under high vacuum.

[0476] Yield: 40.5 g (72.5 mmol, 48%); Purity: >99.9% by HPLC.

[0477] Similarly, the following compounds can be prepared: The catalyst system (palladium source and ligand) used here can be Pd2(dba)3 and SPhos [657408-07-6] (palladium source and ligand), or tetrakis(triphenylphosphine)palladium(0) or bis(triphenylphosphine)palladium(II) chloride [13965-03-2]. Purification can be carried out using column chromatography, or recrystallization or hot extraction can be carried out using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, and 1,4-dioxane. Recrystallization can be carried out using high-boiling solvents such as dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0478] [Table 18-1]

[0479] [Table 18-2]

[0480] [Table 18-3]

[0481] [Table 18-4]

Claims

1. An organic electroluminescent device comprising an anode, a cathode, and at least one organic layer containing at least one light-emitting layer, wherein the at least one light-emitting layer comprises at least one compound of formula (1) as host material 1 and at least one compound of formula (2a) or (2c) as host material 2. 【Chemistry 1】 (wherein the symbols and subscripts used are as follows: X is the same or different in each occurrence, and CR ０ or N, where at least one symbol X is N; X ２ are the same or different in each case, CH, CR １ or N, where there are not more than two symbols X ２ may be N; Y and Y １ is the same or different in each occurrence and is selected from O and S; L, in each occurrence, is the same or different and is a single bond or an aromatic ring system having 6 to 30 aromatic ring atoms; L １ is the same or different in each occurrence and is a single bond or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms; R in each case ０ are independently H, D, or an unsubstituted or partially or fully deuterated aromatic ring system having 6 to 18 carbon atoms; R* at each occurrence is independently D; R is the same or different in each occurrence and is selected from a CN group, an aromatic ring system having 6 to 40 aromatic ring atoms, and a heteroaromatic ring system having 10 to 40 aromatic ring atoms, wherein the ring system is selected from one or more R ２ optionally substituted by radicals, the heteroaromatic ring system is bonded via N when the heteroaromatic ring system contains a nitrogen atom; R １ are in each occurrence the same or different and are selected from the group consisting of CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms; and at the same time, two substituents R bound to the same carbon atom or adjacent carbon atoms are １ However, one or more R ２ It is possible to form mono- or polycyclic aliphatic, aromatic or heteroaromatic ring systems, which may be optionally substituted by radicals; R ２ are in each case the same or different and are H, D, F, Cl, Br, I, CN, NO ２ , N(Ar １ ) ２ , N.H. ２ , N(R ３ ) ２ , C(=O)Ar １ , C(=O)H, C(=O)R ３ , P(=O)(Ar １ ) ２ , a straight chain alkyl, alkoxy or thioalkyl group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 carbon atoms, or an alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which may be selected from the group consisting of one or more R ３ radicals) (wherein one or more non-adjacent CH ２ The group is HC=CH, R ３ C=CR ３ , C≡C, Si(R ３ ) ２ , Ge(R ３ ) ２ , Sn(R ３ ) ２ , C=O, C=S, C=Se, C=NR ３ , P(=O)(R ３ ), SO, SO ２ , N.H., N.R. ３ , O, S, CONH or CONR ３ and one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO ２ and 5 to 60 aromatic ring atoms, each of which may be replaced by one or more R ３ an aromatic or heteroaromatic ring system optionally substituted by a radical, having 5 to 60 aromatic ring atoms and one or more R ３ selected from the group consisting of an aryloxy or heteroaryloxy group optionally substituted by a radical, or a combination of these systems; R ３ are in each occurrence the same or different and are selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN, and by one or more alkyl groups each having 1 to 4 carbon atoms; and at the same time, two or more adjacent R ３ The substituents, taken together, may form a monocyclic or polycyclic aliphatic ring system; Ar １ are the same or different in each occurrence and have 5 to 30 aromatic ring atoms, and one or more non-aromatic R ３ and two Ar radicals bonded to the same nitrogen, phosphorus or boron atom. １ The radical may also be a single bond or N(R ３ ), C(R ３ ) ２ , optionally cross-linked to each other by bridges selected from O and S; Ar in each case ２ and Ar ３ are each independently Ar-1 to Ar-19 【Chemistry 2-1】 【Chemistry 2-2】 [Chemistry 2-3] wherein the dotted line indicates the site of attachment for the radical of formula (1); A in each instance is independently a group represented by formula (3) or (4): 【Transformation 3】 is a group of Ar, in each occurrence, is independently an aryl group having 6 to 40 aromatic ring atoms, optionally substituted with one or more R# radicals, or a heteroaryl group having 5 to 40 aromatic ring atoms, optionally substituted with one or more R# radicals; R# is the same or different in each occurrence and is D, F, Cl, Br, I, CN, NO 2 , C(═O)R 2 , P(═O)(Ar 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , Si(Ar 1 ) 3 , Si(R 2 ) 3 , a linear alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms, each of which may be substituted by one or more R 2 radicals, where one or more non-adjacent CH 2 groups are R 2 C═CR 2 , Si(R 2 ) 2 , C═O, C═S, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 . , O, S or CONR 2 , and one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 ), an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms and optionally substituted in each case by one or more R 2 radicals, an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms and optionally substituted by one or more R 2 radicals, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms and optionally substituted by one or more R 2 radicals; * indicates the site of attachment to formula (2a) or (2c); a, b, and c at each occurrence are each independently 0 or 1, where the sum of the indices a+b+c at each occurrence is 1; m and o in each occurrence are independently 0, 1, 2, 3, or 4; n and p in each occurrence are each independently 0, 1, 2, or 3; In each case, q, r, s, and t are independently 0 or 1. An organic electroluminescent device comprising:

2. 2. The organic electroluminescent device according to claim 1, wherein the symbol Y in the host material 1 represents O.

3. Host material 2 is represented by formula (2d): 【Chemistry 4】 (wherein the symbols and subscripts X ２ , Ar and R １ is as defined in claim 1) 3. The organic electroluminescent device according to claim 1, wherein the organic electroluminescent device satisfies the following:

4. 4. The organic electroluminescent device according to claim 1, wherein in the host material 1, X is N when two or X is N when three.

5. 5. The organic electroluminescent device according to claim 1, wherein the organic electroluminescent device is an electroluminescent device selected from the group consisting of organic light-emitting transistors (OLETs), organic field-quenched devices (OFQDs), organic light-emitting electrochemical cells (OLECs, LECs, LEECs), organic laser diodes (O-lasers), and organic light-emitting diodes (OLEDs).

6. 6. The organic electroluminescent device according to claim 1, wherein the organic electroluminescent device comprises, in addition to the emitting layer (EML), a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), an electron injection layer (EIL) and / or a hole blocking layer (HBL).

7. 7. The organic electroluminescent device according to claim 1, wherein the light-emitting layer, the at least one host material 1 and the at least one host material 2 contain at least one phosphorescent emitter.

8. The phosphorescent emitter is represented by the formula (III) 【Transformation 5】 wherein the symbols and subscripts for formula (III) are as follows: n+m is 3, n is 1 or 2, and m is 2 or 1; X is N or CR; R is H, D, or a branched or straight chain alkyl group or a partially or fully deuterated branched or straight chain alkyl group.

8. The organic electroluminescent device according to claim 7, wherein:

9. A method for manufacturing a device according to any one of claims 1 to 8, characterized in that the light-emitting layer is applied by vapor deposition or from solution.

10. 10. The method of claim 9, wherein the at least one compound of formula (1) and the at least one compound of formula (2), optionally together with the at least one phosphorescent emitter, are deposited sequentially or simultaneously from the vapor phase from at least two material sources to form the emissive layer.

11. 10. The method of claim 9, wherein the at least one compound of formula (1) and the at least one compound of formula (2) are deposited sequentially or simultaneously from the gas phase as a mixture with the at least one phosphorescent emitter to form the emissive layer.

12. 10. The method of claim 9, wherein the at least one compound of formula (1) and the at least one compound of formula (2) are applied from a solution together with the at least one phosphorescent emitter to form the light-emitting layer.

13. At least one compound of formula (1) as host material 1 and at least one compound of formula (2a) or (2c) as host material 2 【Transformation 6】 (wherein the symbols and subscripts used are as follows: X is the same or different in each occurrence, and CR ０ or N, where at least one symbol X is N; X ２ are the same or different in each case, CH, CR １ or N, where there are not more than two symbols X ２ may be N; Y and Y １ is the same or different in each occurrence and is selected from O and S; L, in each occurrence, is the same or different and is a single bond or an aromatic ring system having 6 to 30 aromatic ring atoms; L １ is the same or different in each occurrence and is a single bond or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms; R in each case ０ are independently H, D, or an unsubstituted or partially or fully deuterated aromatic ring system having 6 to 18 carbon atoms; R* in each occurrence is independently D or an aromatic or heteroaromatic ring system having 6 to 18 carbon atoms, which may be partially or fully deuterated; R is the same or different in each occurrence and is selected from a CN group, an aromatic ring system having 6 to 40 aromatic ring atoms, and a heteroaromatic ring system having 10 to 40 aromatic ring atoms, wherein the ring system is selected from one or more R ２ optionally substituted by radicals, the heteroaromatic ring system is bonded via N when the heteroaromatic ring system contains a nitrogen atom; R １ are in each occurrence the same or different and are selected from the group consisting of CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms; and at the same time, two substituents R bound to the same carbon atom or adjacent carbon atoms are １ However, one or more R ２ It is possible to form mono- or polycyclic aliphatic, aromatic or heteroaromatic ring systems, which may be optionally substituted by radicals; R ２ are in each case the same or different and are H, D, F, Cl, Br, I, CN, NO ２ , N(Ar １ ) ２ , N.H. ２ , N(R ３ ) ２ , C(=O)Ar １ , C(=O)H, C(=O)R ３ , P(=O)(Ar １ ) ２ , a straight chain alkyl, alkoxy or thioalkyl group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 carbon atoms, or an alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which may be selected from the group consisting of one or more R ３ radicals) (wherein one or more non-adjacent CH ２ The group is HC=CH, R ３ C=CR ３ , C≡C, Si(R ３ ) ２ , Ge(R ３ ) ２ , Sn(R ３ ) ２ , C=O, C=S, C=Se, C=NR ３ , P(=O)(R ３ ), SO, SO ２ , N.H., N.R. ３ , O, S, CONH or CONR ３ and one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO ２ and 5 to 60 aromatic ring atoms, each of which may be replaced by one or more R ３ an aromatic or heteroaromatic ring system optionally substituted by a radical, having 5 to 60 aromatic ring atoms and one or more R ３ two or more adjacent substituents R ２ However, one or more R ３ optionally capable of forming monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring systems, optionally substituted by radicals; R ３ are in each occurrence the same or different and are selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN, and by one or more alkyl groups each having 1 to 4 carbon atoms; and at the same time, two or more adjacent R ３ The substituents, taken together, may form a monocyclic or polycyclic aliphatic ring system; Ar １ are the same or different in each occurrence and have 5 to 30 aromatic ring atoms, and one or more non-aromatic R ３ and two Ar radicals bonded to the same nitrogen, phosphorus or boron atom. １ The radical may also be a single bond or N(R ３ ), C(R ３ ) ２ , optionally cross-linked to each other by bridges selected from O and S; Ar in each case ２ and Ar ３ each independently have 5 to 40 aromatic ring atoms, and one or more R ２ an aryl or heteroaryl group optionally substituted by a radical; A in each instance is independently a group represented by formula (3) or (4): 【Transformation 7】 is a group of Ar, in each occurrence, is independently an aryl group having 6 to 40 aromatic ring atoms, optionally substituted with one or more R# radicals, or a heteroaryl group having 5 to 40 aromatic ring atoms, optionally substituted with one or more R# radicals; R# is the same or different in each occurrence and is D, F, Cl, Br, I, CN, NO 2 , C(═O)R 2 , P(═O)(Ar 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , Si(Ar 1 ) 3 , Si(R 2 ) 3 , a linear alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms, each of which may be substituted by one or more R 2 radicals, where one or more non-adjacent CH 2 groups are R 2 C═CR 2 , Si(R 2 ) 2 , C═O, C═S, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 . , O, S or CONR 2 , and one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 ), an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms and optionally substituted in each case by one or more R 2 radicals, an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms and optionally substituted by one or more R 2 radicals, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms and optionally substituted by one or more R 2 radicals; * indicates the site of attachment to formula (2a) or (2c); a, b, and c at each occurrence are each independently 0 or 1, where the sum of the indices a+b+c at each occurrence is 1; m and o in each occurrence are independently 0, 1, 2, 3, or 4; n and p in each occurrence are each independently 0, 1, 2, or 3; In each case, q, r, s, and t are independently 0 or 1. A mixture comprising:

14. 14. The mixture according to claim 13, characterized in that the mixture consists of at least one compound of formula (1), at least one compound of formula (2) and a phosphorescent emitter.

15. 15. A formulation comprising the mixture of claim 13 or 14 and at least one solvent.

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