Organic electroluminescent device

Abstract

The present invention relates to an organic electroluminescent device comprising a mixture comprising an electron transport host material and a hole transport host material, and to a formulation comprising the mixture of host materials and to a mixture comprising the host materials. The electron transport host material corresponds to a compound of formula (1) from the class of diphenylene furan or diphenylene sulfide derivatives comprising a substituted pyridine, pyrimidine or triazine unit and a substituted further diphenylene furan or diphenylene sulfide unit.

Description

[0001] This invention relates to an organic electroluminescent device comprising a mixture containing an electron transport host material and a hole transport host material, and to a formulation comprising the mixture of said host materials and a mixture comprising said host materials. The electron transport 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 substituted additional dibenzofuran or dibenzothiophene unit.

[0002] The structures of organic electroluminescent devices (such as OLEDs or OLECs) that use organic semiconductors as functional materials are already well-known. In addition to fluorescent emitters, the luminescent materials used here are increasingly organometallic complexes that exhibit phosphorescence rather than fluorescence. For quantum mechanical reasons, using organometallic compounds as phosphorescent emitters can improve energy efficiency and power efficiency by up to four times. However, in general, improvements are still needed in OLEDs, especially in those exhibiting triplet emission (phosphorescence), for example, in terms of efficiency, operating voltage, and lifetime.

[0003] The characteristics of organic electroluminescent devices depend not only on the light emitter used. In particular, other materials used, such as host and matrix materials, hole-blocking materials, electron transport materials, and electron or exciton-blocking materials, especially the host or matrix materials, are also crucial. Improvements to these materials can lead to significant improvements in electroluminescent devices.

[0004] The host materials used 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, referring to the host material in the context of phosphorescent emitters. This usage of the term also applies to this invention. Meanwhile, various host materials for fluorescent and phosphorescent electronic devices have been developed.

[0005] Another way to improve 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 electron transport materials, hole transport materials, and phosphors in the light-emitting layer of an OLED. This mixture can improve the lifespan of OLEDs compared to existing technologies.

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

[0008] For example, according to KR20120129733, compounds containing two dibenzothiophene units can be used in the luminescent layer.

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

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

[0011] According to WO2015105251, dibenzofuran-dibenzofuran derivatives can be used as the host material, for example, in the light-emitting layer.

[0012] US9771373 describes a specific carbazole derivative as a host material for the light-emitting layer of an electroluminescent device, which can be used in conjunction with another host material.

[0013] KR20160046077 describes specific triazine-dibenzofuran-carbazole and triazine-dibenzothiophene-carbazole derivatives in the luminescent layer, as well as other host materials and specific luminescent agents. Here, the carbazole is bonded to the dibenzofuran or dibenzothiophene unit via a nitrogen atom.

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

[0015] CN107973786 describes triazine-dibenzofuran-carbazole and triazine-dibenzothiophene-carbazole compounds. The triazine substituent is directly bonded at the 1-position of dibenzofuran / dibenzothiophene or via a linker. The carbazole derivative is directly bonded at the 6-position of dibenzofuran / dibenzothiophene via a nitrogen atom or via a linker. These materials are further reported to be miscible with biscarbazole H2 at a ratio of 10:90 to 90:10.

[0016] US2018337348 describes an electronic device that includes two host materials, such as those described in Table 2, in its light-emitting layer.

[0017] WO2018174679 describes an electronic device that includes two host materials, such as those described in Table 19, in its light-emitting layer.

[0018] KR20180061076 describes an electronic device that includes two host materials, such as those described in Table 1, in its light-emitting layer.

[0019] US2019013490 describes an electronic device that includes two host materials, such as those described in Table 3, in its light-emitting layer.

[0020] US20190006590 describes an electronic device comprising two light-emitting layers in a specific order, wherein each light-emitting layer contains 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, wherein 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 bisubstituted triazine-dibenzofuran derivatives and their use as organic materials in organic light-emitting devices.

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

[0024] WO2020022779 describes an organic light-emitting device comprising a first host material containing three inter-bonded dibenzofuran and / or dibenzothiophene units, and a second host material, such as biscarbazole, in the light-emitting layer.

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

[0026] However, improvements are still needed, particularly in terms of the efficiency, operating voltage, and / or lifetime of organic electroluminescent devices, when using these materials or mixtures thereof.

[0027] Therefore, the problem solved by the present invention is to provide a combination of host materials suitable for organic electroluminescent devices, especially for fluorescent or phosphorescent OLEDs, and particularly for resulting in good device performance in terms of improved lifetime, and to provide a corresponding electroluminescent device.

[0028] It has now been found that this problem is solved and the drawbacks of the prior art are eliminated by combining 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 emitting layer of an organic electroluminescent device. Using this material combination to produce the emitting layer in an organic electroluminescent device results in these devices exhibiting very good characteristics, particularly in terms of lifetime, and especially with equal or improved efficiency and / or operating voltage. The advantage also lies particularly in the presence of a luminescent component in the emitting layer, especially when combined with a luminescent material of formula (III) at a concentration between 2 wt% and 15 wt%.

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

[0030]

[0031] The symbols and markings used are as follows:

[0032] X is the same or different in every case and is CR. 0 Or N, where at least one symbol X is N;

[0033] X2 is the same or different in each case and is CH, CR 1 Or N, where no more than two symbols X2 can be N;

[0034] Y and Y1 are the same or different in each case and are selected from O and S;

[0035] L may be the same or different in each case and is a single bond or an aromatic ring system with 6 to 30 aromatic ring atoms;

[0036] L1 may be the same or different in each case and is a single bond or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms;

[0037] R 0 In each case, it is independently H, D, or an aromatic ring system with 6 to 18 carbon atoms that is either unsubstituted or partially or fully deuterated;

[0038] R* is independently D or an aromatic or heteroaromatic ring system with 6 to 18 carbon atoms and can be partially or completely deuterated in each case;

[0039] R# is the same or different in each case and is selected from 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 generated by one or more R 2 Group substitution, wherein one or more non-adjacent CH2 groups can be replaced 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 The hydrogen atoms can be replaced by D, F, Cl, Br, I, CN, or NO2, and the ring has 5 to 40 aromatic ring atoms, and in each case can be replaced by one or more R atoms. 2 Aromatic or heteroaromatic ring systems with substituted groups, having 5 to 40 aromatic ring atoms and capable of being substituted by one or more R groups. 2 A group-substituted aryloxy or heteroaryloxy group, or having 5 to 40 aromatic ring atoms and capable of being substituted by one or more R groups. 2 A group-substituted aralkyl or heteroaralkyl group;

[0040] R may be the same or different in each case and is selected from CN groups, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 10 to 40 aromatic ring atoms, wherein the aromatic ring system and the heteroaromatic ring system may be represented by one or more R groups. 2 Group substitution and wherein, when the heteroaromatic ring system contains a nitrogen atom, the heteroaromatic ring system is via N-bonding;

[0041] R 1 In each case, the same or different and selected from CN, are straight-chain alkyl, alkoxy, or thioalkyl groups having 1 to 20 carbon atoms, or branched or cyclic alkyl, alkoxy, or thioalkyl groups having 3 to 20 carbon atoms, aromatic or heteroaromatic ring systems having 5 to 40 aromatic ring atoms, or aryloxy or heteroaryloxy groups having 5 to 40 aromatic ring atoms, or aralkyl or heteroarylalkyl groups having 5 to 40 aromatic ring atoms; and simultaneously, two substituents R bonded to the same carbon atom or to adjacent carbon atoms. 1It can form monocyclic or polycyclic aliphatic, aromatic, or heterocyclic ring systems, which can be formed by one or more R... 2 Group substitution;

[0042] R 2 In each case, they may be the same or different and are selected from 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 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 substituted by one or more R 3 Group substitution, wherein one or more non-adjacent CH2 groups can be replaced 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 The hydrogen atoms can be replaced by D, F, Cl, Br, I, CN, or NO2, and the ring has 5 to 60 aromatic ring atoms, and in each case can be replaced by one or more R atoms. 3 Aromatic or heteroaromatic ring systems with substituted groups, having 5 to 60 aromatic ring atoms and capable of being substituted by one or more R groups. 3 A group-substituted aryloxy or heteroaryloxy group, or a combination of these systems, wherein two or more adjacent substituents R 2 Optionally, a single-ring or multi-ring aliphatic, aromatic, or heteroaromatic ring system can be formed, wherein the aliphatic, aromatic, or heteroaromatic ring system can be formed by one or more R 3 Group substitution;

[0043] R 3 In each case, the same or different aliphatic hydrocarbon groups selected from H, D, F, CN, having 1 to 20 carbon atoms, or aromatic or heteroaromatic ring systems having 5 to 30 aromatic ring atoms, wherein one or more hydrogen atoms can be replaced by D, F, Cl, Br, I, or CN, and said groups and ring systems can be replaced by one or more alkyl groups each having 1 to 4 carbon atoms; simultaneously, two or more adjacent R 3Substituents can together form monocyclic or polycyclic aliphatic ring systems;

[0044] Ar1 may be the same or different in each case and is a group of 5 to 30 aromatic ring atoms and can be separated by one or more non-aromatic R atoms. 3 Aromatic or heteroaromatic ring systems with substituted groups; simultaneously, two Ar1 groups bonded to the same nitrogen, phosphorus, or boron atom can also be bonded via a single bond or selected from N(R) 3 ), C(R 3 2. The bridge bases of O and S are connected to each other;

[0045] Ar2 and Ar3 are, independently, aromatic ring atoms with 5 to 40 atoms in each case and can be separated by one or more R atoms. 2 A substituted aryl or heteroaryl group;

[0046] A is independently a group of formula (3) or (4) in each case.

[0047]

[0048] Ar is independently an aryl group having 6 to 40 aromatic ring atoms that can be substituted by one or more R# groups, or a heteroaryl group having 5 to 40 aromatic ring atoms that can be substituted by one or more R# groups in each case.

[0049] * Indicates the binding site with the formula (2);

[0050] a, b, and c are each independently 0 or 1 in each case, and the sum of the symbols is 1 in each case a+b+c;

[0051] m and o are independently 0, 1, 2, 3 or 4 in each case;

[0052] n and p are each independently 0, 1, 2, or 3 in each case; and

[0053] q, r, s, and t are each independently 0 or 1 in each case.

[0054] The present invention also provides a method for preparing an organic electroluminescent device and a mixture comprising at least one compound of formula (1) and at least one compound of formula (2), a specific combination of materials, and an formulation containing such a mixture or combination of materials. The corresponding preferred embodiments described below also constitute part of the subject matter of the present invention. Surprising and advantageous effects are achieved through a specific selection of compounds of formula (1) and compounds of formula (2).

[0055] The organic electroluminescent devices of the present invention include, for example, organic light-emitting transistors (OLETs), organic field quenching devices (OFQDs), organic light-emitting electrochemical cells (OLECs, LECs, LEECs), organic laser diodes (O-lasers), or organic light-emitting diodes (OLEDs). The organic electroluminescent devices of the present invention are particularly organic light-emitting diodes or organic light-emitting electrochemical cells. The devices of the present invention are more preferably OLEDs.

[0056] The organic layer of the device of the present invention, comprising a material combination containing at least one compound of formula (1) and at least one compound of formula (2) as described above or below, preferably includes, in addition to the light-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). The device of the present invention may also include multiple layers selected from EML, HIL, HTL, ETL, EIL, and HBL.

[0057] However, the device may also include inorganic materials or other layers formed entirely of inorganic materials.

[0058] The luminescent layer containing at least one compound of formula (1) and at least one compound of formula (2) is preferably a phosphorescent layer, characterized in that, in addition to the host material combination containing the compounds of formula (1) and formula (2) as described above, it also contains at least one phosphorescent emitter. Suitable selection of emitters and preferred emitters is described below.

[0059] In the context of this invention, aryl groups contain 6 to 40 aromatic ring atoms, preferably carbon atoms. Heteroaryl groups in the context of this invention contain 5 to 40 aromatic ring atoms, wherein the ring atoms comprise carbon atoms and at least one heteroatom, provided that the sum of the carbon atoms and the heteroatom is at least 5. The heteroatom is preferably selected from N, O, and / or S. Aryl groups or heteroaryl groups are to be understood herein to refer to simple aromatic rings derived from benzene, i.e., phenyl, or, for example, simple heteroaryl rings derived from pyridine, pyrimidine, or thiophene, or, for example, fused aryl or heteroaryl groups derived from naphthalene, anthracene, phenanthrene, quinoline, or isoquinoline. Therefore, aryl groups having 6 to 18 carbon atoms are preferably phenyl, naphthyl, phenanthrene, or biphenylidene, wherein the connection of aryl groups as substituents is not limited. Aryl or heteroaryl groups in the context of this invention may contain one or more R groups, wherein the substituents R are as described below.

[0060] In the context of this invention, aromatic ring systems contain 6 to 40 carbon atoms. The aromatic ring systems also include aryl groups as described above.

[0061] The aromatic ring system having 6 to 18 carbon atoms is preferably selected from phenyl, fully deuterated phenyl, biphenyl, naphthyl, phenanthryl and triphenylide.

[0062] In the context of this invention, heteroaromatic ring systems contain 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. The heteroaromatic ring system further includes heteroaryl groups as described above. The heteroatom in the heteroaromatic ring system is preferably selected from N, O, and / or S.

[0063] In the context of this invention, aromatic or heteroaromatic ring systems should be understood to refer to systems that do not necessarily contain only aryl or heteroaromatic groups, but in which multiple aryl or heteroaromatic groups can also be interrupted by non-aromatic units (preferably less than 10% of non-H atoms), such as carbon, nitrogen, or oxygen atoms or carbonyl groups. For example, systems such as 9,9'-spirodifluorene, 9,9-diarylfluorene, triarylamines, diaryl ethers, piracene, etc., should therefore also be considered aromatic or heteroaromatic ring systems in the context of this invention, as well as systems in which two or more aryl groups are interrupted by, for example, straight-chain or cyclic alkyl groups or by silyl groups. Furthermore, systems in which two or more aryl or heteroaromatic groups are directly bonded to each other, such as biphenyl, terphenyl, tetraphenyl, or bipyridine, are also covered by the definition of aromatic or heteroaromatic ring systems.

[0064] Aromatic or heteroaromatic ring systems having 5-40 aromatic ring atoms and being able to connect to aromatic or heteroaromatic systems at any desired position should be understood to refer to groups derived, for example, from the following substances: benzene, naphthalene, anthracene, benzo[a]anthracene, phenanthrene, benzo[a]phenanthrene, pyrene, celestine, perylene, fluoranthene, benzo[a]fluoranthene, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, diphenylidene, terphenyl, terphenylidene, fluorene, spirofluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indeno[a]fluorene, cis or trans Monobenzone-indofluorene, cis or trans dibenzone-indofluorene, trimer indene, isotrimer indene, spirotrimer indene, spiroisotrimer indene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, indole-carbazole, indole-carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenanthridine Azides, pyrazoles, indazoles, imidazoles, benzimidazoles, naphthiazoles, phenanthreneimidazoles, pyridinium imidazoles, pyrazinium imidazoles, quinoxaline imidazoles azole, benzo[ azole, naphtho azole, anthraquinone azole, phenanthrene azole, isotonic Azole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1,5-diazathane, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperylene, pyrazine, phenazine, phenazine Azides, phenothiazines, fluorescent rings, naphthidine, azacarbazole, benzo[a]carbline, phenanthroline, 1,2,3-triazoles, 1,2,4-triazoles, benzo[a]triazoles, 1,2,3- diazole, 1,2,4- diazole, 1,2,5- diazole, 1,3,4- Diazole, 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, tetrazolium, 1,2,4,5-tetraazine, 1,2,3,4-tetraazine, 1,2,3,5-tetraazine, purine, pteridine, indazine, and benzothiadiazole.

[0065] The abbreviation Ar1 may be the same or different in each case and is a ring with 5 to 30 aromatic atoms and can be divided by one or more non-aromatic R atoms. 3 Aromatic or heteroaromatic ring systems with substituted groups; simultaneously, two Ar1 groups bonded to the same nitrogen, phosphorus, or boron atom can also be bonded via a single bond or selected from N(R) 3 ), C(R 3 2. The bridging bases of O and S are bridged to each other, wherein R 3 Group or substituent R 3 It has the definition described above or below. Preferably, Ar1 is an aryl group having 6 to 40 aromatic ring atoms as described above. Most preferably, Ar1 is a group that can be generated by one or more non-aromatic R groups. 3 A phenyl group with a substituent. Ar1 is preferably unsubstituted.

[0066] The abbreviation Ar2, in each case independently, is an aromatic ring with 5 to 40 atoms and can be divided by one or more R atoms. 2 A group-substituted aryl or heteroaryl group, wherein the R 2 Group or substituent R 2 As defined above or below. The details given for aryl and heteroaryl groups having 5 to 40 aromatic ring atoms apply accordingly.

[0067] The abbreviation Ar3, in each case independently, is an aromatic ring with 5 to 40 atoms and can be divided by one or more R atoms. 2 A group-substituted aryl or heteroaryl group, wherein the R 2 Group or substituent R2 As defined above or below. The details given for aryl and heteroaryl groups having 5 to 40 aromatic ring atoms apply accordingly.

[0068] The abbreviation Ar, in each case independently, refers to an aryl group having 6 to 40 aromatic ring atoms that may be substituted by one or more R# groups, or a heteroaryl group having 5 to 40 aromatic ring atoms that may be substituted by one or more R# groups, wherein details regarding the aryl group or heteroaryl group apply accordingly, as described above. The one or more R# groups have the definitions described above or below. The abbreviation Ar, in each case preferably independently, refers to an aryl group having 6 to 40 aromatic ring atoms that may be substituted by one or more R# groups, or a heteroaryl group having 5 to 40 aromatic ring atoms and containing O or S as a heteroatom, wherein the group may be substituted by one or more R# groups, wherein details regarding the aryl group, heteroaryl group, and R# as described above or below apply accordingly.

[0069] In the context of this invention, cyclic alkyl, alkoxy, or thioalkyl groups should be understood to refer to monocyclic, bicyclic, or polycyclic groups.

[0070] In the context of this invention, C1 to C1 are straight-chain, branched, or cyclic. 20Alkyl groups should be understood to refer to, for example, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, sec-pentyl, tert-pentyl, 2-pentyl, neopentyl, cyclopentyl, n-hexyl, sec-hexyl, tert-hexyl, 2-hexyl, 3-hexyl, neohexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl Cycloheptayl, 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-hept-1-yl, 1,1-dimethyl 1,1-dimethyl-n-octyl-1-yl, 1,1-dimethyl-n-dodecane-1-yl, 1,1-dimethyl-n-tetradecane-1-yl, 1,1-dimethyl-n-hexadecane-1-yl, 1,1-dimethyl-n-octadecane-1-yl, 1,1-diethyl-n-hexyl-1-yl, 1,1-diethyl-n-heptane-1-yl, 1,1-diethyl-n-octyl-1-yl, 1,1-diethyl-n- Dec-1-yl, 1,1-diethyl-n-dodecane-1-yl, 1,1-diethyl-n-tetradecane-1-yl, 1,1-diethyl-n-hexadecane-1-yl, 1,1-diethyl-n-octadecane-1-yl, 1-(n-propyl)cyclohexyl-1-yl, 1-(n-butyl)cyclohexyl-1-yl, 1-(n-hexyl)cyclohexyl-1-yl, 1-(n-octyl)cyclohexyl-1-yl and 1-(n-decyl)cyclohexyl-1-yl groups.

[0071] C1 to C1 of straight or branched chains 20 The alkoxy group should be understood to refer to, for example, methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, or 2-methylbutoxy.

[0072] Straight chain C1 to C 20 The term "thioalkyl group" should be understood to refer to, for example, an S-alkyl group, such as thiomethyl, 1-thioethyl, 1-thio-isopropyl, 1-thio-n-propyl, 1-thioisobutyl, 1-thio-n-butyl, or 1-thio-tert-butyl.

[0073] An aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms refers to an O-aryl or O-heteroaryl group, and means that the aryl or heteroaryl group is bonded via an oxygen atom, wherein the aryl or heteroaryl group is as defined above.

[0074] An aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms refers to an alkyl group as described above that is replaced by an aryl group or heteroaralkyl group, wherein the aryl or heteroaralkyl group is as defined above.

[0075] In the context of this invention, a phosphorescent emitter is a compound that exhibits luminescence from an excited state with high spin multiplicity, i.e., an excited state with spin > 1, particularly from an excited triplet state. In the context of this application, all luminescent complexes containing transition metals or lanthanides are considered phosphorescent emitters. A more precise definition is given below.

[0076] When the host material of the luminescent layer comprising at least one compound of formula (1) as described above or hereinafter preferred and at least one compound of formula (2) as described above or hereinafter preferred, is used in a phosphorescent emitter, it is preferred that its triplet energy is not significantly less than the triplet energy of the phosphorescent emitter. Regarding the triplet energy level, it is preferred that T1(emissor) – T1(matrix) ≤ 0.2 eV, more preferably ≤ 0.15 eV, and most preferably ≤ 0.1 eV. Here, T1(matrix) is the triplet energy level of the matrix material in the luminescent layer, and this applies to each of the two matrix materials, and T1(emissor) is the triplet energy level of the phosphorescent emitter. If the luminescent layer contains more than two matrix materials, the above relationship preferably also applies to each of the additional matrix materials.

[0077] The following describes the main material 1 present in the device of the present invention and its preferred embodiments. The preferred embodiments of the main material 1 of formula (1) are also applicable to the mixtures and / or formulations of the present invention.

[0078] In the compounds of formula (1), the symbol Y is O or S.

[0079] In a preferred embodiment of the compound of formula (1), the symbol Y is preferably O.

[0080] Therefore, the present invention also provides an electroluminescent device as described above, wherein Y in the host material 1 is O.

[0081] Where Y is preferably O, the compound of formula (1) can be described by formulas (1a) and (1b).

[0082]

[0083] Ar2, Ar3, L1, R*, n, m, L, R, p, Y1, and o have the definitions given above or the preferred definitions given below.

[0084] In a preferred embodiment of the compound of formula (1), the symbol Y is preferably S.

[0085] Therefore, the present invention also provides an electroluminescent device as described above, wherein Y in the host material 1 is S.

[0086] Where Y is preferably S, the compound of formula (1) can be described by formulas (1c) and (1d).

[0087]

[0088] Ar2, Ar3, L1, R*, n, m, L, R, p, Y1, and o have the definitions given above or the preferred definitions given below.

[0089] In preferred embodiments of the compounds of formulas (1), (1a), (1b), (1c), and (1d) or the main materials of formulas (1), (1a), (1b), (1c), and (1d), the symbol X represents CR. 0 Or N, wherein at least one X group is N.

[0090] The substituent

[0091]

[0092] Therefore, it has the following definition, where * indicates the binding site with dibenzofuran or dibenzothiophene via L1, and R 0 Ar2 and Ar3 have the definitions given above or are given preferred definitions:

[0093]

[0094] In the main material 1, X is preferably N in two cases and one of X is CR. 0 , or all X are N.

[0095] Therefore, the present invention also provides an electroluminescent device as described above or as preferred, wherein, in the host material 1, the symbol X is N in both cases and one X is CR. 0 , or the symbol X is N in three cases.

[0096] In the main material 1, all X are more preferably N, where R 0 It has the definition given above or below.

[0097] R 0 In each case, the same or different, and preferably selected from H, D, or unsubstituted or partially or fully deuterated aromatic ring systems with 6 to 18 carbon atoms. R 0 In each case, H, D, or an unsubstituted aromatic ring system having 6 to 18 carbon atoms is preferred. 0 H is preferred in each case.

[0098] In preferred embodiments of the compounds of formulas (1), (1a), (1b), (1c) and (1d) or the host materials of formulas (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.

[0099] In preferred embodiments of the compounds of formulas (1), (1a), (1b), (1c), and (1d) or the host materials of formulas (1), (1a), (1b), (1c), and (1d), the linker L1 is preferably a bond or a linker selected from L-1 to L-20.

[0100]

[0101] In preferred embodiments of the compounds of formulas (1), (1a), (1b), (1c) and (1d) or the host materials of formulas (1), (1a), (1b), (1c) and (1d), the linker L1 is more preferably a bond or a linker selected from L-2 and L-3.

[0102] In a preferred embodiment of the compounds of formulas (1), (1a), (1b), (1c) and (1d) or the host materials of formulas (1), (1a), (1b), (1c) and (1d), the linker L1 is most preferably a bond.

[0103] In preferred embodiments of the compounds of formulas (1), (1a), (1b), (1c) and (1d) or the host materials of formulas (1), (1a), (1b), (1c) and (1d), the linker L is a single bond or an aromatic ring system having 6 to 30 aromatic ring atoms.

[0104] In a preferred embodiment of the compounds of formulas (1), (1a), (1b), (1c) and (1d) or the host materials of formulas (1), (1a), (1b), (1c) and (1d), the linker L is preferably a bond or a linker selected from L-1 to L-20 as described above.

[0105] In a preferred embodiment of the compounds of formulas (1), (1a), (1b), (1c) and (1d) or the host materials of formulas (1), (1a), (1b), (1c) and (1d), the linker L is more preferably a bond or a linker selected from L-2 and L-3.

[0106] In preferred embodiments of the compounds of formulas (1), (1a), (1b), (1c) and (1d) or the host materials of formulas (1), (1a), (1b), (1c) and (1d), the linker L is most preferably a bond.

[0107] In preferred embodiments of the compounds of formulas (1), (1a), (1b), (1c) and (1d) or the main materials of formulas (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 definition given above or below.

[0108] In preferred embodiments of the compounds of formulas (1), (1a), (1b), (1c) and (1d) or the main materials of formulas (1), (1a), (1b), (1c) and (1d), p is preferably 0 or 1, more preferably 0, wherein R has the preferred definition given above or below.

[0109] In preferred embodiments of the compounds of formulas (1), (1a), (1b), (1c) and (1d) or the main materials of formulas (1), (1a), (1b), (1c) and (1d), m is preferably 0, 1 or 2, more preferably 0 or 1, wherein R* has the preferred definition given above or below.

[0110] In preferred embodiments of the compounds of formulas (1), (1a), (1b), (1c) and (1d) or the main materials of formulas (1), (1a), (1b), (1c) and (1d), n is preferably 0 or 1, more preferably 0, wherein R* has the preferred definition given above or below.

[0111] R* may be the same or different in each case and is preferably selected from D or aromatic or heteroaromatic ring systems having 6 to 18 carbon atoms and being partially or completely deuterated. R* is preferably phenyl, 1,3-biphenyl, 1,4-biphenyl, dibenzofuranyl or dibenzothiopheneyl in each case. R* is more preferably phenyl, 1,3-biphenyl, 1,4-biphenyl or dibenzofuranyl in each case.

[0112] R may be the same or different in each case and is selected from CN groups, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 10 to 40 aromatic ring atoms, wherein the aromatic ring system and heteroaromatic ring system may be composed of one or more R groups. 2 The group is substituted and wherein, when the heteroaromatic ring system contains a nitrogen atom, the heteroaromatic ring system is N-bonded. R is preferably independently phenyl, terphenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, N-carbazoleyl, fluorenyl, spirodifluorenyl, indolocarbazoleyl, indobenzocarbazoleyl, or indobenzocarbazoleyl, and the group may be one or more R. 2Group substitution. The N-carbazole group is preferably substituted with a phenyl group. R is more preferably, in each case, independently phenyl, terphenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, N-carbazole, fluorenyl, spirodifluorenyl, indolocarbazole, indobenzocarbazole, or a phenyl-substituted N-carbazole group. R is most preferably, in each case, independently phenyl, dibenzofuranyl, or a phenyl-substituted N-carbazole group.

[0113] The compound of formula (1a) is a preferred embodiment of the compound of formula (1) and the host material 1.

[0114] In preferred embodiments of the compounds of formulas (1), (1a), (1b), (1c) and (1d) or the main materials of formulas (1), (1a), (1b), (1c) and (1d), Y1 is O or S, preferably O.

[0115] In preferred embodiments of the compounds of formulas (1), (1a), (1b), (1c), and (1d) or the host materials of formulas (1), (1a), (1b), (1c), and (1d), each Ar2 is preferably independently an aryl group having 6 to 40 carbon atoms as described above or preferred, and the aryl group may be generated by one or more R 2 Group substitution, or a heteroaryl group having 10 to 40 carbon atoms as described above, wherein the heteroaryl group can be replaced by one or more R groups. 2 Group substitution. Here, two or more R groups bonded to the same carbon atom or to adjacent carbon atoms. 2 The groups can form monocyclic or polycyclic aliphatic, aromatic, or heteroaromatic ring systems, which can be formed by one or more R groups. 3 Group substitution.

[0116] There are no restrictions on the connection of aryl groups or heteroaryl groups, and they can be connected via carbon atoms or via heteroatoms such as nitrogen atoms.

[0117] Ar2 can preferably be selected from the following groups Ar-1 to Ar-19, wherein R 2 Ar1 has the definition specified or specified as preferred above, and wherein two heteroatoms are excluded via R 2 Or Ar1 can be directly connected to each other:

[0118]

[0119]

[0120] The dashed lines indicate the bonding sites with groups of formula (1), (1a), (1b), (1c) or (1d).

[0121] More preferably, Ar2 is Ar-1, Ar-2, Ar-3, Ar-6, Ar-14, Ar-17, and Ar-18, wherein R 2 Ar1 has the definition specified above or below as preferred.

[0122] In preferred embodiments of the compounds of formulas (1), (1a), (1b), (1c), and (1d) or the host materials of formulas (1), (1a), (1b), (1c), and (1d), each Ar3 is preferably independently an aryl group having 6 to 40 carbon atoms as described above or preferred, and the aryl group may be generated by one or more R 2 Group substitution, or a heteroaryl group having 10 to 40 carbon atoms as described above, wherein the heteroaryl group can be replaced by one or more R groups. 2 Group substitution. Here, two or more R groups bonded to the same carbon atom or to adjacent carbon atoms. 2 The groups can form monocyclic or polycyclic aliphatic, aromatic, or heteroaromatic ring systems, which can be formed by one or more R groups. 3 Group substitution.

[0123] There are no restrictions on the connection of aryl groups or heteroaryl groups, and they can be connected via carbon atoms or via heteroatoms such as nitrogen atoms.

[0124] Ar3 can preferably be selected from the following groups Ar-1 to Ar-19, wherein R 2 Ar1 has the definition specified or specified as preferred above, and wherein two heteroatoms are excluded via R 2 Or Ar1 are directly connected to each other.

[0125] More preferably, Ar3 is Ar-1, Ar-2, and Ar-3, wherein R 2 Ar1 has the definition specified above or below as preferred.

[0126] As described above, the R in the substituents of formulas Ar-1 to Ar-19 2 Preferably selected from H, D, CN, having 5 to 40 aromatic ring atoms, and in each case can be substituted by one or more R atoms. 3 Aromatic or heteroaromatic ring systems with substituted groups.

[0127] R in the substituents of formulas Ar-1 to Ar-19 as described above 2 More preferably, it is H, D, phenyl or N-carbazolyl.

[0128] In the substituents of Ar-13 to Ar-16 as described above, Ar1 is preferably phenyl.

[0129] The connection of groups via linker L1 or L in compounds of formulas (1), (1a), (1b), (1c) and (1d) or preferred compounds of formulas (1), (1a), (1b), (1c) and (1d) is not limited and can be via any carbon atom.

[0130] More preferably, substituents

[0131]

[0132] The compound of formula (1) is bonded at position 1 via a linker L1 to a group of formula (1), (1a), (1b), (1c), or (1d). For a compound of formula (1), it can be represented by formula (1e):

[0133]

[0134] Ar2, Ar3, X, L1, R*, n, m, Y, L, R, p, o, and Y1 have the definitions given above or given as preferred.

[0135] The substituent

[0136]

[0137] It can be bonded at any position to groups of formulas (1), (1a), (1b), (1c), (1d), and (1e) via a linker L, as indicated herein by substituents P-1 to P-4 and P-6 to P-9:

[0138] Wherein the * mark is the bonding site with the linker L, and R, p, o and Y1 have the definitions described above or preferred.

[0139] More preferably, P-1 is bonded to the linker L.

[0140] More preferably, the substituents described above or with respect to P-1 to P-4 and P-5 to P-9 The compounds are linked via a linker L to the remainder of formulas (1), (1a), (1b), (1c), (1d), and (1e), connecting to the 6- or 8-position of the central dibenzofuran or dibenzothiophene. For compounds of formula (1), this is represented by compounds of formulas (1f) and (1g):

[0141]

[0142] Where X, Ar2, Ar3, L1, Y, R*, n, m, L, R, p, o, L, and Y1 have the definitions given above or given as preferred, and the substituents

[0143]

[0144] It also has the preferred definition as described above.

[0145] R in the compounds of the preferred formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), and (1g) as described above or as such 3 Preferably, in each case, the compounds are independently selected from H, CN, and aromatic or heteroaromatic ring systems having 5 to 40 aromatic ring atoms, wherein one or more hydrogen atoms may be replaced by D or CN. R in the compounds described above or as preferred by formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), and (1g) 3 More preferably, in each case, it is independently selected from H, phenyl, or deuterated phenyl.

[0146] Examples of suitable host materials of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g) in the electroluminescent devices of the present invention, selected and preferably combined with at least one compound of formula (2), are the structures given in Table 1 below.

[0147] Table 1:

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228] In the electroluminescent device of the present invention, the compounds of particularly suitable formulas (1), (1a), (1b), (1c), (1d) and (1e) for use in combination with at least one compound of formula (2) are compounds E1 to E54.

[0229] Table 2:

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236] The preparation of the compounds of formula (1) or the preferred compounds from Table 1 and compounds E1 to E54 is known to those skilled in the art. These compounds can be prepared by synthetic steps known to those skilled in the art, such as bromination, Suzuki coupling, Ullmann coupling, Hartwig-Buchwald coupling, etc. Suitable synthetic methods are shown in general in Scheme 1 below, wherein the symbols and notations used have the definitions given above.

[0237] Option 1:

[0238]

[0239] The following describes the main material 2 present in the device of the present invention and its preferred embodiments. The preferred embodiments of the main material 2 of formula (2) are also applicable to the mixtures and / or formulations of the present invention.

[0240] Main material 2 is at least one compound of formula (2),

[0241]

[0242] The symbols and markings used are as follows:

[0243] A is independently a group of formula (3) or (4) in each case.

[0244]

[0245] X2 is the same or different in each case and is CH, CR 1 Or N, where no more than two symbols X2 can be N;

[0246] * Indicates the binding site with the formula (2);

[0247] R 1 In each case, the same or different and selected from CN, are straight-chain alkyl, alkoxy, or thioalkyl groups having 1 to 20 carbon atoms, or branched or cyclic alkyl, alkoxy, or thioalkyl groups having 3 to 20 carbon atoms, aromatic or heteroaromatic ring systems having 5 to 40 aromatic ring atoms, or aryloxy or heteroaryloxy groups having 5 to 40 aromatic ring atoms, or aralkyl or heteroarylalkyl groups having 5 to 40 aromatic ring atoms; and simultaneously, two substituents R bonded to the same carbon atom or to adjacent carbon atoms. 1 It can form monocyclic or polycyclic aliphatic, aromatic, or heterocyclic ring systems, which can be formed by one or more R... 2 Group substitution;

[0248] Ar is, in each case, independently an aryl group having 6 to 40 aromatic ring atoms that can be substituted by one or more R# groups; or a heteroaryl group having 5 to 40 aromatic ring atoms that can be substituted by one or more R# groups;

[0249] R# is the same or different in each case and is selected from 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 generated by one or more R 2 Group substitution, wherein one or more non-adjacent CH2 groups can be replaced 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 The hydrogen atoms can be replaced by D, F, Cl, Br, I, CN, or NO2, and the ring has 5 to 40 aromatic ring atoms, and in each case can be replaced by one or more R atoms. 2 Aromatic or heteroaromatic ring systems with substituted groups, having 5 to 40 aromatic ring atoms and capable of being substituted by one or more R groups. 2 A group-substituted aryloxy or heteroaryloxy group, or having 5 to 40 aromatic ring atoms and capable of being substituted by one or more R groups. 2 A group-substituted aralkyl or heteroaralkyl group;

[0250] R 2 In each case, they may be the same or different and are selected from 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 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 substituted by one or more R 3 Group substitution, wherein one or more non-adjacent CH2 groups can be replaced by HC=CH, R3 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 The hydrogen atoms can be replaced by D, F, Cl, Br, I, CN, or NO2, and the ring has 5 to 60 aromatic ring atoms, and in each case can be replaced by one or more R atoms. 3 Aromatic or heteroaromatic ring systems with substituted groups, having 5 to 60 aromatic ring atoms and capable of being substituted by one or more R groups. 3 A group-substituted aryloxy or heteroaryloxy group, or a combination of these systems, wherein two or more adjacent substituents R 2 Optionally, a single-ring or multi-ring aliphatic, aromatic, or heteroaromatic ring system can be formed, wherein the aliphatic, aromatic, or heteroaromatic ring system can be formed by one or more R 3 Group substitution;

[0251] R 3 In each case, the same or different aliphatic hydrocarbon groups selected from H, D, F, CN, having 1 to 20 carbon atoms, or aromatic or heteroaromatic ring systems having 5 to 30 aromatic ring atoms, wherein one or more hydrogen atoms can be replaced by D, F, Cl, Br, I, or CN, and said groups and ring systems can be replaced by one or more alkyl groups each having 1 to 4 carbon atoms; simultaneously, two or more adjacent R 3 Substituents can together form monocyclic or polycyclic aliphatic ring systems;

[0252] Ar1 may be the same or different in each case and is a group of 5 to 30 aromatic ring atoms and can be separated by one or more non-aromatic R atoms. 3 Aromatic or heteroaromatic ring systems with substituted groups; simultaneously, two Ar1 groups bonded to the same nitrogen, phosphorus, or boron atom can also be bonded via a single bond or selected from N(R) 3 ), C(R 3 2. The bridge bases of O and S are connected to each other;

[0253] a, b, and c are each independently 0 or 1 in each case, and the sum of the symbols is 1 in each case a + b + c; and

[0254] q, r, s, and t are each independently 0 or 1 in each case.

[0255] In one embodiment of the invention, for the device of the invention, a compound of formula (2) as described above is selected and used in the light-emitting layer together with a compound of formula (1) as described above or preferred, or with a compound from Table 1 or compounds E1 to E54.

[0256] In the compound of formula (2), a, b, and c are each independently 0 or 1 in each case, and the sum of the labels is 1 in each case a+b+c. c is preferably defined as 1.

[0257] The compound of formula (2) can be represented by the following formulas (2a), (2b) and (2c):

[0258]

[0259] Among them, A and R 1 q, r, s, and t have the definitions given above or below. Here, the compound of formula (2a) is preferably given.

[0260] Therefore, the present invention also 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).

[0261] R in compounds of formula (2) and (2a) to (2c) as described above, or preferably in compounds of formula (2) and (2a) to (2c) 1 In each case, the same or different and selected from: 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 heteroaromatic group having 5 to 40 aromatic ring atoms, or an aralkyl or heteroaromatic group having 5 to 40 aromatic ring atoms; and simultaneously, two substituents R bonded to the same carbon atom or bonded to adjacent carbon atoms. 1 It can form monocyclic or polycyclic aliphatic, aromatic, or heterocyclic ring systems, which can be formed by one or more R... 2 Group substitution.

[0262] If two or more R 1 If the group is bonded to an adjacent carbon atom, the monocyclic or polycyclic aliphatic, aromatic, or heteroaromatic ring system is preferably selected from (S-1) to (S-4).

[0263] Among them, Ar1 and R 2It has the definition given above or the definition given as preferred, and # indicates the bonding site with the rest of the corresponding structure, such as the bonding site with the adjacent position identified by X2 in the compounds of formulas (2), (2a), (2b) and (2c). Here, (S-1) or (S-2) is particularly preferred.

[0264] R in compounds of formula (2) and (2a) to (2c) as described above, or preferably in compounds of formula (2) and (2a) to (2c) 1 In each case, the same or different and preferably selected from CN, are straight-chain alkyl, alkoxy, or thioalkyl groups having 1 to 20 carbon atoms, or branched or cyclic alkyl, alkoxy, or thioalkyl groups having 3 to 20 carbon atoms, aromatic or heteroaromatic ring systems having 5 to 40 aromatic ring atoms, aryloxy or heteroaryloxy groups having 5 to 40 aromatic ring atoms, or aralkyl or heteroarylalkyl groups having 5 to 40 aromatic ring atoms. Substituent R 1 In each case, CN or an aryl group having 6 to 40 carbon atoms as described above is preferred independently. 1 In each case, phenyl is preferred independently.

[0265] In compounds of formula (2), (2a), (2b) or (2c), the sum of the labels q+r+s is preferably 0, 1 or 2, where R 1 With the definition given above. In compounds of formula (2), (2a), (2b) or (2c), the sum of the labels q+r+s is preferably 0 or 1, where R 1 It has the definition given above.

[0266] In compounds of formula (2), (2a), (2b), or (2c), q, r, and s are preferably 0 or 1. Preferably, q is 1 if the sum of the labels q + r + s is 1. Preferably, q, r, and s are 0.

[0267] In equation (4),

[0268]

[0269] q, r, and s are either 0 or 1, where R 1 It has the definitions given above. Preferably, the sum of the marks q+r+s in equation (4) is 0 or 1. In equation (4), q, r and s are more preferably 0.

[0270] In equation (3),

[0271]

[0272] In each case, t is preferably 0 or 1 independently. In equation (3), t is preferably the same and is 0.

[0273] In the compounds of formulas (2), (2a), (2b), and (2c), or preferably of formulas (2), (2a), (2b), and (2c), X2 is the same or different in each case and is CH, CR 1 Or N, where no more than two symbols X2 can be N.

[0274] In the compounds of formulas (2), (2a), (2b), and (2c), or preferably the compounds of formulas (2), (2a), (2b), and (2c), X2 is preferably the same or different in each case and is CH, CR 1 Or N, where no more than one symbol X2 is N.

[0275] In compounds of formulas (2), (2a), (2b), and (2c), or preferably compounds of formulas (2), (2a), (2b), and (2c), X2 is more preferably the same or different in each case and is CH in both cases and CR in both cases. 1 Or, in three cases it is CH and in one case it is CR. 1 In which the substituent R 1 Each case independently has the definition given above.

[0276] Ar is, in each case, independently an aryl group having 6 to 40 aromatic ring atoms that may be substituted by one or more R# groups, or a heteroaryl group having 5 to 40 aromatic ring atoms that may be substituted by one or more R# groups, wherein the R# group has the definition given above or preferably given below.

[0277] Ar is preferably, in each case independently, an aryl group having 6 to 40 aromatic ring atoms that can be substituted by one or more R# groups, or a heteroaryl group having 5 to 40 aromatic ring atoms and containing O or S as heteroatoms, wherein the group can be substituted by one or more R# groups, wherein the R# groups have the definitions given above or preferably given above.

[0278] Ar is preferably an aryl group having 6 to 18 carbon atoms and being substituted by one or more R# groups, or a dibenzofuranyl or dibenzothiophenyl group being substituted by one or more R# groups, wherein the R# group has the definition given above or preferably given below.

[0279] Ar is more preferably phenyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, 1,3-biphenyl, 1,4-biphenyl, terphenyl, tetraphenyl, naphthyl, fluorenyl, 9,9-diphenylfluorenyl, bisspirofluorenyl, biphenylimide, dibenzofuranyl, phenyl-substituted dibenzofuranyl, dibenzothiopheneyl, or phenyl-substituted dibenzothiopheneyl. Ar is most preferably phenyl, 1,3-biphenyl, 1,4-biphenyl, naphth-2-yl, or terphenyl-2-yl.

[0280] In compounds of formulas (2), (2a), (2b), and (2c), or preferably compounds of formulas (2), (2a), (2b), and (2c), R# may be the same or different in each case and is preferably selected from D, CN, and compounds having 5 to 40 aromatic ring atoms and may be one or more R# in each case. 2 Aromatic or heteroaromatic ring systems with substituted groups.

[0281] In the compounds of formulas (2), (2a), (2b) and (2c) or preferred compounds of formulas (2), (2a), (2b) and (2c), R# is the same or different in each case and is more preferably an unsubstituted aromatic ring system having 5 to 20 aromatic ring atoms, preferably phenyl.

[0282] In a preferred embodiment of the invention, A conforms to formula (4) as described above or has substituents described as preferred.

[0283] In a preferred embodiment of the invention, A conforms to formula (3) as described above or has substituents described as preferred.

[0284] Compounds of formulas (2), (2a), (2b), and (2c) whose A satisfies formula (3) and whose q, r, s, and t are 0 can be represented by formulas (2d) and (2e).

[0285]

[0286] X2 and Ar have the definitions given above or given as preferred.

[0287] Therefore, the present invention also 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).

[0288] In a preferred embodiment of the compounds of formula (2), (2a), (2b), (2c), (2d), or (2e), the substituents of formulas (3) and (4) are each connected to each other at the 2 or 5 position of indodo[3,2,1-jk]carbazole, as illustrated in the schematic form below, wherein the dashed lines indicate the bonding with the substituents of formulas (3) and (4):

[0289]

[0290] Examples of suitable host materials of formulas (2), (2a), (2b), (2c), (2d) and (2e) selected according to the present invention and preferably combined with at least one compound of formula (1) for use in the electroluminescent devices of the present invention are the structures given in Table 3 below.

[0291] Table 3:

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299] In the electroluminescent device of the present invention, the compounds of formula (2) that are particularly suitable for use in combination with at least one compound of formula (1) are compounds H1 to H21 in Table 4.

[0300] Table 4:

[0301]

[0302]

[0303]

[0304] The compounds of formula (2) that are particularly suitable for use in the electroluminescent devices of the present invention, preferably in combination with at least one compound of formula (1), are compounds H1, H3, H4, H5, H6, H7, H8, H11 and H12.

[0305] The preparation of compounds of formula (2) or preferred compounds of formulas (2), (2a), (2b), (2c), (2d), and (2e), as well as compounds from Table 3 and compounds H1 to H21, is known to those skilled in the art. These compounds can be prepared by synthetic steps known to those skilled in the art, such as bromination, Suzuki coupling, Ullmann coupling, Hartwig-Buchwald coupling, etc. Suitable synthetic methods are shown in general in Scheme 2 below, wherein the symbols and notations used have the definitions given above.

[0306] Option 2:

[0307]

[0308]

[0309] The main materials of the aforementioned formula (1) and their descriptions are preferred embodiments or compounds from Table 1 and compounds E1 to E54 can be combined in the device of the present invention as needed with the main materials of the aforementioned formulas (2), (2a), (2b), (2c), (2d) and (2e) and their descriptions are preferred embodiments or compounds from Table 3 or compounds H1 to H21.

[0310] The present invention also provides a mixture comprising at least one compound of formula (1) as main material 1 and at least one compound of formula (2) as main material 2.

[0311]

[0312]

[0313] The symbols and markings used are as follows:

[0314] X is the same or different in every case and is CR. 0 Or N, where at least one symbol X is N;

[0315] X2 is the same or different in each case and is CH, CR 1 Or N, where no more than two symbols X2 can be N;

[0316] Y and Y1 are the same or different in each case and are selected from O and S;

[0317] L may be the same or different in each case and is a single bond or an aromatic ring system with 6 to 30 aromatic ring atoms;

[0318] L1 may be the same or different in each case and is a single bond or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms;

[0319] R 0 In each case, it is independently H, D, or an aromatic ring system with 6 to 18 carbon atoms that is either unsubstituted or partially or fully deuterated;

[0320] R* is independently D or an aromatic or heteroaromatic ring system with 6 to 18 carbon atoms and can be partially or completely deuterated in each case;

[0321] R# is the same or different in each case and is selected from 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 generated by one or more R 2 Group substitution, wherein one or more non-adjacent CH2 groups can be replaced 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 The hydrogen atoms can be replaced by D, F, Cl, Br, I, CN, or NO2, and the ring has 5 to 40 aromatic ring atoms, and in each case can be replaced by one or more R atoms. 2 Aromatic or heteroaromatic ring systems with substituted groups, having 5 to 40 aromatic ring atoms and capable of being substituted by one or more R groups. 2 A group-substituted aryloxy or heteroaryloxy group, or having 5 to 40 aromatic ring atoms and capable of being substituted by one or more R groups. 2 A group-substituted aralkyl or heteroaralkyl group;

[0322] R may be the same or different in each case and is selected from CN groups, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 10 to 40 aromatic ring atoms, wherein the aromatic ring system and heteroaromatic ring system may be composed of one or more R groups. 2 Group substitution and wherein, when the heteroaromatic ring system contains a nitrogen atom, the heteroaromatic ring system is via N-bonding;

[0323] R 1In each case, the same or different and selected from CN, are straight-chain alkyl, alkoxy, or thioalkyl groups having 1 to 20 carbon atoms, or branched or cyclic alkyl, alkoxy, or thioalkyl groups having 3 to 20 carbon atoms, aromatic or heteroaromatic ring systems having 5 to 40 aromatic ring atoms, or aryloxy or heteroaryloxy groups having 5 to 40 aromatic ring atoms, or aralkyl or heteroarylalkyl groups having 5 to 40 aromatic ring atoms; and simultaneously, two substituents R bonded to the same carbon atom or to adjacent carbon atoms. 1 It can form monocyclic or polycyclic aliphatic, aromatic, or heterocyclic ring systems, which can be formed by one or more R... 2 Group substitution;

[0324] R 2 In each case, they may be the same or different and are selected from 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 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 substituted by one or more R 3 Group substitution, wherein one or more non-adjacent CH2 groups can be replaced 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 The hydrogen atoms can be replaced by D, F, Cl, Br, I, CN, or NO2, and the ring has 5 to 60 aromatic ring atoms, and in each case can be replaced by one or more R atoms. 3 Aromatic or heteroaromatic ring systems with substituted groups, having 5 to 60 aromatic ring atoms and capable of being substituted by one or more R groups. 3 A group-substituted aryloxy or heteroaryloxy group, or a combination of these systems, wherein two or more adjacent substituents R 2 Optionally, a single-ring or multi-ring aliphatic, aromatic, or heteroaromatic ring system can be formed, wherein the aliphatic, aromatic, or heteroaromatic ring system can be formed by one or more R 3 Group substitution;

[0325] R 3 In each case, the same or different aliphatic hydrocarbon groups selected from H, D, F, CN, having 1 to 20 carbon atoms, or aromatic or heteroaromatic ring systems having 5 to 30 aromatic ring atoms, wherein one or more hydrogen atoms can be replaced by D, F, Cl, Br, I, or CN, and said groups and ring systems can be replaced by one or more alkyl groups each having 1 to 4 carbon atoms; simultaneously, two or more adjacent R 3 Substituents can together form monocyclic or polycyclic aliphatic ring systems;

[0326] Ar1 may be the same or different in each case and is a group of 5 to 30 aromatic ring atoms and can be separated by one or more non-aromatic R atoms. 3 Aromatic or heteroaromatic ring systems with substituted groups; simultaneously, two Ar1 groups bonded to the same nitrogen, phosphorus, or boron atom can also be bonded via a single bond or selected from N(R) 3 ), C(R 3 2. The bridge bases of O and S are connected to each other;

[0327] Ar2 and Ar3 are, independently, aromatic ring atoms with 5 to 40 atoms in each case and can be separated by one or more R atoms. 2 A substituted aryl or heteroaryl group;

[0328] A is independently a group of formula (3) or (4) in each case.

[0329]

[0330] Ar is independently an aryl group having 6 to 40 aromatic ring atoms that can be substituted by one or more R# groups, or a heteroaryl group having 5 to 40 aromatic ring atoms that can be substituted by one or more R# groups in each case.

[0331] * Indicates the binding site with the formula (2);

[0332] a, b, and c are each independently 0 or 1 in each case, wherein the sum of the labels is 1 in each instance (a+b+c).

[0333] m and o are independently 0, 1, 2, 3 or 4 in each case;

[0334] n and p are each independently 0, 1, 2, or 3 in each case; and

[0335] q, r, s, and t are each independently 0 or 1 in each case.

[0336] Details regarding the main materials of formulas (1) and (2) and their preferred embodiments also apply accordingly to the mixtures of the present invention.

[0337] The particularly preferred body material of formula (1) and the body material of formula (2) used in the device of the present invention are obtained by combining compounds E1 to E54 with compounds from Table 3.

[0338] The mixture of the very particularly preferred body material of formula (1) and the body material of formula (2) used in the device of the present invention is obtained by combining compounds E1 to E54 with compounds H1 to H21, as shown in Table 5 below.

[0339] Table 5:

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351] Based on the entire mixture or the entire composition of the light-emitting layer, the concentration of the electron transport host material of the preferred formula (1) in the mixture of the present invention or in the light-emitting layer of the device of the present invention, as described above or as preferably, is in the range of 5 wt% to 90 wt%, preferably in the range of 10 wt% to 85 wt%, more preferably in the range of 20 wt% to 85 wt%, even more preferably in the range of 30 wt% to 80 wt%, very particularly preferably in the range of 20 wt% to 60 wt%, and most preferably in the range of 30 wt% to 50 wt%.

[0352] Based on the entire mixture or the entire composition of the light-emitting layer, the concentration of the hole transport host material of the preferred formula (2) in the mixture of the present invention or in the light-emitting layer of the device of the present invention, as described above or as preferably, is in the range of 10 wt% to 95 wt%, preferably in the range of 15 wt% to 90 wt%, more preferably in the range of 15 wt% to 80 wt%, even more preferably in the range of 20 wt% to 70 wt%, very particularly preferably in the range of 40 wt% to 80 wt%, and most preferably in the range of 50 wt% to 70 wt%.

[0353] The present invention also relates to a mixture that, in addition to containing the main materials 1 and 2 described above or preferably as described above, especially mixtures M1 to M1134, contains at least one phosphorescent material.

[0354] The present invention also relates to an organic electroluminescent device as described above or preferably, wherein the light-emitting layer comprises, in addition to the main materials 1 and 2 described above or preferably, especially material combinations M1 to M1134, at least one phosphorescent material.

[0355] The term "phosphorescent luminescent material" generally encompasses compounds that emit light through spin-forbidden transitions from excited states with higher spin multiplicity (i.e., spin state > 1), such as from triplet states or states with higher spin quantum numbers, such as quintet states. This should preferably be understood as referring to transitions from triplet states.

[0356] Suitable phosphorescent emitters (= triplet emitters) are, in particular, compounds that emit light upon appropriate excitation, preferably in the visible region, and further contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, more preferably greater than 56 and less than 80, especially metals having this atomic number. Preferred phosphorescent emitters are compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium, especially compounds containing iridium or platinum. In the context of this invention, all luminescent compounds containing the aforementioned metals are considered phosphorescent emitters.

[0357] Generally speaking, all phosphorescent complexes for phosphorescent OLEDs that are known to those skilled in the art, such as those in the field of organic electroluminescent devices, are suitable.

[0358] Examples of the aforementioned luminescent materials can be found in applications WO 2016 / 015815, WO 00 / 70655, WO 2001 / 41512, WO 2002 / 02714, WO 2002 / 15645, EP 1191613, EP 1191612, EP 1191614, WO 05 / 033244, WO05 / 019373, US 2005 / 0258742, WO 2009 / 146770, WO 2010 / 015307, WO 2010 / 031485, WO2010 / 054731, WO 2010 / 054728, WO 2010 / 086089, WO 2010 / 099852, WO 2010 / 102709、WO2011 / 032626、WO 2011 / 066898、WO 2011 / 157339、WO 2012 / 007086、WO 2014 / 008982、WO2014 / 023377、WO 2014 / 094961、WO 2014 / 094960、WO 2015 / 036074、WO 2015 / 104045、WO2015 / 117718、WO 2016 / 015815、WO 2016 / 124304、WO 2017 / 032439、WO 2015 / 036074, WO2015 / 117718 and WO 2016 / 015815.

[0359] According to the present invention, the preferred phosphorescent emitter conforms to formula (III).

[0360]

[0361] The symbols and notations for equation (III) are defined as follows:

[0362] When n+m is 3, n is 1 or 2, and m is 2 or 1.

[0363] X is N or CR.

[0364] R is H, D, or a branched or straight-chain alkyl group, or a partially or fully deuterated branched or straight-chain alkyl group.

[0365] Therefore, the present invention also provides an organic electroluminescent device as described above or as preferred, characterized in that the light-emitting layer, in addition to comprising the host materials 1 and 2, also comprises at least one phosphorescent emitter that conforms to formula (III) as described above.

[0366] In the light emitter of formula (III), n is preferably 1 and m is preferably 2.

[0367] In the luminescent body of formula (III), preferably, one X is selected from N and the other X is CR.

[0368] In the luminescent body of formula (III), at least one R is preferably different from H.

[0369] In the luminescent body of formula (III), it is preferred that the two Rs are different from H and have one of the other definitions given above for the luminescent body of formula (III).

[0370] According to the preferred phosphorescent emitters of the present invention, formulas (Ia), (IIa) and (IIIa) are met.

[0371]

[0372] The symbols and notations for these equations (Ia), (IIa), and (IIIa) are defined as follows:

[0373] R1 is H or D, 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 that may be partially or fully substituted with deuterium.

[0374] According to the preferred phosphorescent emitters of the present invention, formulas (IVa), (Va), and (VIa) are used.

[0375]

[0376] The symbols and notations for these formulas (IVa), (Va), and (VIa) are defined as follows:

[0377] R1 is H or D, 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 that may be partially or fully substituted with deuterium.

[0378] Preferred examples of phosphorescent luminescent materials are listed in Table 6 below.

[0379] Table 6:

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400] Preferred examples of phosphorescent multipods are listed in Table 7 below.

[0401] Table 7:

[0402]

[0403]

[0404]

[0405]

[0406] In the mixture of the present invention or the light-emitting layer of the device of the present invention, it is preferred to include any mixture 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, M55, M56, M57. M58, M59, M60, M61, M62, M63, M64, M65, M66, M67, M68, M69, M70, M71, M72, M7 3. M74, M75, M76, M77, M78, M79, M80, M81, M82, M83, M84, M85, M86, M87, M88, M89, M90, M91, M92, M93, M94, M95, M96, M97, M98, M99, M100, M101, M102, M10 3. M104, M105, M106, M107, M108, M109, M110, M111, M112, M113, M114, M115, M 116, M117, M118, M119, M120, M121, M122, M123, M124, M125, M126, M127, M12 8. M129, M130, M131, M132, M133, M134, M135, M136, M137, M138, M139, M140, M141, M142, M143, M144, M145, M146, M147, M148, M149, M150, M151, M152, M1 53. M154, M155, M156, M157, M158, M159, M160, M161, M162, M163, M164, M165, M166, M167, M168, M169, M170, M171, M172, M173, M174, M175, M176, M177, M1 78. M179, M180, M181, M182, M183, M184, M185, M186, M187, M188, M189, M190, M191, M192, M193, M194, M195, M196, M197, M198, M199, M200, M201, M202, M2 03. 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, M413, M414, M415M416、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、M801、M802、M8 03、M804、M805、M806、M807、M808、M809、M810、M811、M812、M813、M814、M815、M816、M817、M818、M819、M820、M821、M822、M823、M824、M825、M826、M827、M8 28、M829、M830、M831、M832、M833、M834、M835、M836、M837、M838、M839、M840、 M841、M842、M843、M844、M845、M846、M847、M848、M849、M850、M851、M852、M8 53、M854、M855、M856、M857、M858、M859、M860、M861、M862、M863、M864、M865、 M866、M867、M868、M869、M870、M871、M872、M873、M874、M875、M876、M877、M8 78、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、M1008、M1009、M10 10、M1011、M1012、M1013、M1014、M1015、M1016、M1017、M1018、M1019、M1020、M1021, M1022, M1023, M1024, M1025, M1026, M1027, M1028, M1029, M1030, M1031, M1032, M1033, M1034, M1035, M10 36. M1037, M1038, M1039, 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, M1066, M10 67. M1068, M1069, M1070, M1071, M1072, M1073, M1074, M1075, M1076, M1077, M1078, M1079, M1080, M1081, M1082, M 1083, M1084, M1085, M1086, M1087, M1088, M1089, M1090, M1091, M1092, M1093, M1094, M1095, M1096, M1097, M109 8. M1099, M1100, M1101, M1102, M1103, M1104, M1105, M1106, M1107, M1108, M1109, M1110, M1111, M1112, M1113, M 1114, M1115, M1116, M1117, M1118, M1119, M1120, M1121, M1122, M1123, M1124, M1125, M1126, M1127, M1128, M1129, M1130, M1131, M1132, M1133, and M1134 are combined with compounds of formulas (III), (Ia), (IIa), (IIIa), (IVa), (Va), and (VIa) or compounds from Table 6 or Table 7.

[0407] The light-emitting layer in the organic electroluminescent device of the present invention, which contains at least one phosphorescent emitter, is preferably an infrared light-emitting layer or a 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.

[0408] The yellow emitting layer should be understood herein as a layer having a maximum photoluminescence value in the range of 540 to 570 nm. The orange emitting layer should be understood as a layer having a maximum photoluminescence value in the range of 570 to 600 nm. The red emitting layer should be understood as a layer having a maximum photoluminescence value in the range of 600 to 750 nm. The green emitting layer should be understood as a layer having a maximum photoluminescence value in the range of 490 to 540 nm. The blue emitting layer should be understood as a layer having a maximum photoluminescence value in the range of 440 to 490 nm. The maximum photoluminescence value of the layers is here determined by measuring the photoluminescence spectrum of a layer with a thickness of 50 nm at room temperature, the layer having a combination of the host material of formulas (1) and (2) of the present invention with a suitable emitting body.

[0409] The photoluminescence spectrum of the layer was recorded, for example, using a commercial photoluminescence spectrometer.

[0410] The photoluminescence spectrum of the selected luminescent material is typically in the range of 10 at room temperature. -5 The measurement is performed in an oxygen-free solution at a concentration of moles. A suitable solvent is any solvent in which the selected luminescent material is dissolved at the stated concentration. Particularly suitable solvents are typically toluene or 2-methyl-THF, as well as dichloromethane. Measurements are performed using a commercial photoluminescence spectrometer. The triplet energy T1 (in eV) is determined from the photoluminescence spectrum of the luminescent material. First, the peak maximum value PL of the photoluminescence spectrum is determined. 最大 (in nm). Then, the peak value PL is calculated using the following formula. 最大 (in nm) to eV conversion: E(T1, in eV) = 1240 / E(T1, in nm) = 1240 / PL 最大 (in nm).

[0411] Therefore, the preferred phosphorescent emitter is an infrared emitter, preferably having formulas (III), (Ia), (IIa), (IIIa), (IVa), (Va), (VIa) or from Table 6 or Table 7, with its triplet energy T1 preferably being about 1.9 eV to about 1.0 eV.

[0412] Therefore, the preferred phosphorescent emitter is a red emitter, preferably having formulas (III), (Ia), (IIa), (IIIa), (IVa), (Va), (VIa) or from Table 6 or Table 7, and its triplet energy T1 is preferably about 2.1 eV to about 1.9 eV.

[0413] Therefore, the preferred phosphorescent emitter is a yellow emitter, preferably having formulas (III), (Ia), (IIa), (IIIa), (IVa), (Va), (VIa) or from Table 6 or Table 7, and its triplet energy T1 is preferably about 2.3 eV to about 2.1 eV.

[0414] Therefore, the preferred phosphorescent emitter is a green emitter, preferably having formulas (III), (Ia), (IIa), (IIIa), (IVa), (Va), (VIa) or from Table 6 or Table 7, and its triplet energy T1 is preferably about 2.5 eV to about 2.3 eV.

[0415] Therefore, the preferred phosphorescent emitter is a blue emitter, preferably having formulas (III), (Ia), (IIa), (IIIa), (IVa), (Va), (VIa) or from Table 6 or Table 7, with its triplet energy T1 preferably being about 3.1 eV to about 2.5 eV.

[0416] Therefore, the preferred phosphorescent emitters are those of formulas (III), (Ia), (IIa), (IIIa), (IVa), (Va), (VIa) or ultraviolet emitters from Table 6 or Table 7, with a triplet energy T1 preferably of about 4.0 eV to about 3.1 eV.

[0417] Therefore, the particularly preferred phosphorescent emitters are green or yellow emitters, which, as described above, preferably have formulas (III), (Ia), (IIa), (IIIa), (IVa), (Va), (VIa) or those from Table 6 or Table 7.

[0418] Therefore, the most particularly preferred phosphorescent emitter is a green emitter, preferably having formulas (III), (Ia), (IIa), (IIIa), (IVa), (Va), (VIa) or from Table 6 or Table 7, with its triplet energy T1 preferably being about 2.5 eV to about 2.3 eV.

[0419] Most preferably, the green light emitters having the preferred formulas (III), (Ia), (IIa), (IIIa), (IVa), (Va), (VIa) as described above, or those from Table 6 or Table 7, are selected for use in the compositions of the present invention or the light-emitting layers of the present invention.

[0420] Fluorescent light emitters can also be present in the light-emitting layer of the device of the present invention.

[0421] Preferred fluorescent emitters are selected from the arylamine category. In the context of this invention, arylamines or aromatic amines should be understood as compounds containing three substituted or unsubstituted aromatic or heteroaromatic ring systems directly bonded to 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 anthraceneamines, aromatic anthracene diamines, aromatic pyreneamines, aromatic pyrene diamines, aromatic pyrine amines, or aromatic pyrine diamines. Aromatic anthraceneamines should be understood as compounds in which a diaryl amino group is directly bonded to an anthracene group, preferably at the 9-position. Aromatic anthracene diamines should be understood as compounds in which two diaryl amino groups are directly bonded to an anthracene group, preferably at the 9 or 10-position. Aromatic pyreneamines, pyrene diamines, pyrine amines, and pyrine diamines are defined in a similar manner, wherein the diaryl amino group is preferably bonded to pyrene at the 1-position or the 1,6-position. Other preferred phosphors are: indoxfluoreneamine or indoxfluorene diamine, for example according to WO 2006 / 108497 or WO 2006 / 122630; benzo[a]indoxfluoreneamine or benzo[a]indoxfluorene diamine, for example according to WO 2008 / 006449; and dibenzo[a]indoxfluoreneamine or dibenzo[a]indoxfluorene diamine, for example according to WO 2007 / 140847; and indoxfluorene derivatives having fused aryl groups disclosed in WO 2010 / 012328.

[0422] In another preferred embodiment of the invention, at least one light-emitting layer of the organic electroluminescent device may contain, in addition to the host materials 1 and 2 as described above or as preferred, another host material or matrix material, referred to as a hybrid matrix system. The hybrid matrix system preferably contains three or four different matrix materials, more preferably three different matrix materials (in other words, in addition to host materials 1 and 2 as described above, there is one other matrix component). Particularly suitable matrix materials that can be combined as matrix components in the hybrid matrix system are selected from wide-bandgap materials, bipolar host materials, electron transport materials (ETM), and hole transport materials (HTM).

[0423] Wide bandgap material is to be understood herein as a material within the scope of the disclosure of US 7,294,849, characterized by a bandgap of at least 3.5 eV, wherein the bandgap is to be understood as the interval between the HOMO and LOMO energies of the material.

[0424] In one embodiment of the invention, the mixture contains no other components, i.e., functional materials, besides the electron transport host material of formula (1) and the hole transport host material of formula (2). These are material mixtures used directly in the fabrication of the light-emitting layer. These mixtures are also referred to as premixed systems, which serve as the sole material source in the vapor deposition of the host material for the light-emitting layer and have a constant mixing ratio during vapor deposition. In this way, vapor deposition of a layer with uniformly distributed components can be achieved in a simple and rapid manner without the need for precise control of multiple material sources.

[0425] In an alternative embodiment of the invention, in addition to the components of the electron transport host material of formula (1) and the hole transport host material of formula (2), the mixture also comprises the phosphorescent emitter as described above. As mentioned above, given a suitable mixing ratio during vapor deposition, the mixture can also be used as the sole material source.

[0426] Therefore, the components or constituent parts of the light-emitting layer of the device of the present invention can be obtained by vapor deposition or by processing from solution. The host materials 1 and 2, as described above or as preferred, are provided, optionally in combination with materials of the phosphorescent emitter as described above or as preferred, for use in formulations containing at least one solvent. These formulations can be, for example, solutions, dispersions, or emulsions. For this purpose, a mixture of two or more solvents may preferably be used.

[0427] Therefore, the present invention also provides a formulation comprising the main materials 1 and 2 as described above, optionally combined with a phosphorescent emitter as described or preferred, and a mixture of the present invention with at least one solvent.

[0428] Suitable and preferred solvents include, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, naphthol, veratrine, THF, methyl-THF, THP, chlorobenzene, and dimethylbenzene. Alkane, phenoxytoluene, especially 3-phenoxytoluene, (-)-fonone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, α-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, naphthane, dodecylbenzene Ethyl benzoate, indane, methyl benzoate, NMP, p-isopropyltoluene, phenethyl ether, 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, hexamethylindane, or mixtures of these solvents.

[0429] The formulation may also contain at least one additional organic or inorganic compound, which is also used in the light-emitting layer of the device of the present invention, especially additional light-emitting compounds and / or additional matrix materials.

[0430] Based on the entire composition of the luminescent material and the matrix material, the luminescent layer and luminescent compound in the device of the present invention according to a preferred embodiment contain a matrix material comprising at least one compound of formula (1) and at least one compound of formula (2) according to a preferred embodiment, preferably between 99.9 vol% and 1 vol%, more preferably between 99 vol% and 10 vol%, particularly preferably between 98 vol% and 60 vol%, and very particularly preferably between 97 vol% and 80 vol%. Accordingly, based on the entire composition of the luminescent layer comprising the luminescent material and the matrix material, the luminescent layer in the device of the present invention preferably contains a luminescent material comprising between 0.1 vol% and 99 vol%, more preferably between 1 vol% and 90 vol%, more preferably between 2 vol% and 40 vol%, and most preferably between 3 vol% and 20 vol%. If the compound is processed from a solution, it is preferable to use the corresponding amount by weight % instead of the above-mentioned amount by volume %.

[0431] According to the preferred embodiment and the luminescent compound, the luminescent layer in the device of the present invention preferably contains a matrix material of formula (1) and a matrix material of formula (2) in a volume percentage ratio between 3:1 and 1:3, preferably between 1:2.5 and 1:1, and more preferably between 1:2 and 1:1. If the compound is processed from a solution, it is preferable to use the corresponding weight % ratio instead of the above volume % ratio.

[0432] The preferred layer order in the organic electroluminescent device of the present invention is as follows:

[0433] Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / electron injection layer / cathode.

[0434] This layer order is the preferred order.

[0435] At the same time, it should be pointed out again that not all of the aforementioned layers must exist and / or other layers may exist in addition.

[0436] The organic electroluminescent device of the present invention may contain two or more light-emitting layers. At least one light-emitting layer is the light-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 light-emitting layers in this case have a total of several emission peaks between 380 nm and 750 nm, such that the overall result is white light emission; in other words, various light-emitting compounds that can emit fluorescence or phosphorescence and emit blue, yellow, orange, or red light are used in the light-emitting layers. A three-layer system, i.e., a system having three light-emitting layers, wherein the three layers exhibit blue, green, and orange or red light emission (for the basic construction, see, for example, WO 2005 / 011013). It should be noted that for the generation of white light, it may also be suitable to use a single light-emitting compound that emits light over a wide wavelength range instead of multiple light-emitting compounds.

[0437] Suitable charge transport materials that can be used in the hole injection or hole transport layer or electron blocking layer or electron transport layer of the organic electroluminescent device of the present invention are, for example, compounds disclosed in Y. Shirota et al., Chem. Rev. 2007, 107(4), 953-1010, or other materials used in these layers according to the prior art.

[0438] Materials that can be used in the electron transport layer are any materials used as electron transport materials in the electron transport layer according to existing technology. Particularly suitable are aluminum complexes such as Alq3, zirconium complexes such as Zrq4, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, and quinoline derivatives. Diazole derivatives, aromatic ketones, lactams, boranes, phosphazacyclopentane derivatives, and phosphine oxide derivatives. Other suitable materials are derivatives of the above compounds, such as those disclosed in JP 2000 / 053957, WO 2003 / 060956, WO 2004 / 028217, WO 2004 / 080975, and WO2010 / 072300.

[0439] Preferred hole transport materials, particularly those suitable for hole transport, hole injection, or electron blocking layers, include, for example, indene-fluoreneamine derivatives (e.g., according to WO 06 / 122630 or WO 06 / 100896), amine derivatives disclosed in EP 1661888, hexaazatriphenylide derivatives (e.g., according to WO 01 / 049806), amine derivatives having a fused aromatic system (e.g., according to US 5,061,569), amine derivatives disclosed in WO 95 / 09147, monobenzo-indenefluoreneamine (e.g., according to WO 08 / 006449), dibenzo-indenefluoreneamine (e.g., according to WO 07 / 140847), and spirodifluoreneamine (e.g., according to WO 2012 / 034627 or an undisclosed EP). 12000929.5), fluoreneamines (e.g., according to WO 2014 / 015937, WO2014 / 015938 and WO 2014 / 015935), spirodibenzopyranamines (e.g. according to WO 2013 / 083216) and dihydroacridine derivatives (e.g. according to WO 2012 / 150001).

[0440] Suitable cathodes for the devices of the present invention are metals, metal alloys, or multilayer structures with low work function, comprising a variety of metals such as alkaline earth metals, alkali metals, group metals, or lanthanides (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Alloys comprising alkali metals or alkaline earth metals and silver are also suitable, such as alloys comprising magnesium and silver. In the case of multilayer structures, other metals with relatively high work function, such as Ag or Al, may also be used in addition to the aforementioned metals. In this case, combinations of metals, such as Ca / Ag, Mg / Ag, or Ba / Ag, are typically used. It is also preferable to introduce a thin interlayer of material with a high dielectric constant between the metal cathode and the organic semiconductor. Examples of suitable materials for this purpose are alkali metal fluorides or alkaline earth metal fluorides, and may also be corresponding oxides or carbonates (e.g., LiF, Li₂O, BaF₂, MgO, NaF, CsF, Cs₂CO₃, etc.). Lithium quinoline (LiQ) may also be used for this purpose. The thickness of this layer is preferably between 0.5 and 5 nm.

[0441] The preferred anode is a material with a high work function. Preferably, the anode has a work function greater than 4.5 eV relative to vacuum. Firstly, metals with high redox potentials, such as Ag, Pt, or Au, are suitable for this purpose. Secondly, metal / metal oxide electrodes (e.g., Al / Ni / NiO) are also preferred. x Al / PtO xFor some applications, at least one electrode must be transparent or partially transparent to enable irradiation of organic materials (organic solar cells) or light emission (OLEDs, O-lasers). The preferred anode material is a conductive mixed metal oxide. Indium tin oxide (ITO) or indium zinc oxide (IZO) is particularly preferred. Furthermore, conductive doped organic materials, especially conductive doped polymers, are preferred. Additionally, the anode may 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).

[0442] During the manufacturing process, the organic electroluminescent device of the present invention is appropriately structured (according to the application), contact connections are provided, and finally sealed, because the lifespan of the device of the present invention is shortened in the presence of water and / or air.

[0443] The fabrication of the device of the present invention is not limited herein. One or more organic layers, including the light-emitting layer, can be coated by a sublimation method. In this case, at less than 10 -5 millibars, preferably less than 10 -6 The material is applied via vapor deposition in a vacuum sublimation system at an initial pressure of millibars. However, the initial pressure can also be lower, for example, less than 10. -7 millibar.

[0444] A preferred feature of the organic electroluminescent device of the present invention is that one or more layers are coated by an OVPD (organic vapor deposition) method or by means of carrier gas sublimation. In this case, the material is in a state between 10 -5 The material is applied at a pressure between millibar and 1 bar. A special case of this method is the OVJP (Organic Vapor Jetting) method, in which the material is applied directly through a nozzle and thus structured (e.g., MS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).

[0445] A further preferred feature of the organic electroluminescent device of the present invention is that one or more organic layers comprising the composition of the present invention are produced from a solution, for example by spin coating, or by any printing method such as screen printing, flexographic printing, nozzle printing, or offset printing, but more preferably by LITI (photoinduced thermal imaging, thermal transfer) or inkjet printing. For this purpose, soluble host materials 1 and 2 and a phosphorescent emitter are required. Processing from solution has the advantages that, for example, the luminescent layer can be applied in a very simple and inexpensive manner. This technique is particularly suitable for the large-scale manufacture of organic electroluminescent devices.

[0446] Furthermore, a mixing method is possible, in which, for example, one or more layers are applied from a solution and one or more additional layers are applied by vapor deposition.

[0447] These methods are generally known to those skilled in the art and can be applied to organic electroluminescent devices.

[0448] Therefore, the present invention also provides a method for manufacturing an organic electroluminescent device as described above or preferred in the present invention, characterized in that the light-emitting layer is applied by vapor deposition, especially by sublimation and / or by OVPD (organic vapor deposition) and / or by means of carrier gas sublimation, or applied from a solution, especially by spin coating or by printing.

[0449] In the case of fabrication via vapor deposition, there are, in principle, two methods to apply or vapor deposit the luminescent layer of the present invention onto any substrate or prior layer. First, the materials used can be initially loaded into material sources and ultimately evaporated from different material sources (“co-evaporation”). Second, various materials can be premixed (premixed system), and the mixture can be initially loaded into a single material source and ultimately evaporated from that source (“premixed evaporation”). In this way, vapor deposition of a luminescent layer with a uniformly distributed composition can be achieved simply and quickly without the need for precise control of multiple material sources.

[0450] Therefore, the present invention also provides a method for manufacturing the device of the present invention, characterized in that at least one compound of formula (1) as described above or preferred and at least one compound of formula (2) as described above or preferred are continuously or simultaneously deposited from at least two material sources from the vapor phase, optionally deposited together with at least one phosphorescent emitter as described above or preferred, and forming an emitting layer.

[0451] In a preferred embodiment of the invention, the light-emitting layer is applied by vapor deposition, wherein the components of the composition are premixed and evaporated from a single material source.

[0452] Therefore, the present invention also provides a method for manufacturing the device of the present invention, characterized in that at least one compound of formula (1) and at least one compound of formula (2) are deposited from the vapor phase as a mixture with at least one phosphorescent emitter to form an emitting layer.

[0453] The present invention also provides a method for manufacturing the device of the present invention as described above or preferred, characterized in that at least one compound of formula (1) and at least one compound of formula (2) as described above or preferred are applied from a solution together with at least one phosphorescent material to form a light-emitting layer.

[0454] The device of the present invention is characterized by the following surprising advantages compared to the prior art:

[0455] As described above, the combination of materials 1 and 2 described above results in an increase in device lifespan.

[0456] As is clear in the examples given below, by comparing data from OLEDs with those from the prior art, it can be determined that, regardless of the emitter concentration, the present invention’s combination of matrix materials in the EML results in an increase in device lifetime of approximately 19% to 65%.

[0457] It should be noted that variations of the embodiments described herein are all covered by the scope of this invention. Unless expressly excluded, any feature disclosed herein may be replaced by an alternative feature having the same or equivalent or similar purpose. Therefore, unless otherwise stated, any feature disclosed herein should be considered as an example of a class series or as an equivalent or similar feature.

[0458] All features of this invention can be combined with each other in any way, unless particular features and / or steps are mutually exclusive. This applies in particular to preferred features of the invention. Similarly, features that are not necessarily combined can be used alone (rather than in combination).

[0459] The technical teachings disclosed in this invention can be refined and combined with other embodiments.

[0460] The invention is illustrated in more detail by way of the following embodiments, but is not intended to limit the invention thereto.

[0461] General methods :

[0462] In all quantum chemical calculations, the Gaussian16 (Revision B.01) software package was used. The neutral singlet ground state was optimized at the B3LYP / 6-31G(d) level. At the B3LYP / 6-31G(d) level, the HOMO and LUMO values ​​were determined for the ground state energy optimized with B3LYP / 6-31G(d). TD-DFT singlet and triplet excitations (vertical excitations) were then calculated using the same method (B3LYP / 6-31G(d)), utilizing the optimized ground state geometry. Standard settings for SCF and gradient convergence were used.

[0463] Based on energy calculations, the HOMO (Homo Optica Molar) as the last orbital occupied by two electrons (αocc. eigenvalue) and the LUMO (Luminous Unoccupied Orbital) as the first unoccupied orbital (αvirt. eigenvalue) are given, in Hartree units, where HEh and LEh represent the HOMO energy (in Hartree units) and the LUMO energy (in Hartree units), respectively. The HOMO and LUMO values ​​(in electron volts) are thus determined and calibrated using cyclic voltammetry, as follows:

[0464] HOMOcorr=0.90603*HOMO-0.84836

[0465] LUMOcorr=0.99687*LUMO-0.72445.

[0466] The triplet energy level T1 of a material is defined as the relative excitation energy (in eV) of the lowest-energy triplet state discovered through quantum chemical energy calculations.

[0467] The singlet energy level S1 of a material is defined as the relative excitation energy (in eV) of the singlet state with the second lowest energy, as discovered through quantum chemical energy calculations.

[0468] The lowest singlet state in terms of energy is called S0.

[0469] The method described in this article is independent of the software package used and always yields the same results. Examples of commonly used programs for this purpose are "Gaussian09" (Gaussian Corporation) and Q-Chem4.1 (Q-Chem Corporation). In this example, the energy is calculated using the software package "Gaussian16 (Revision B.01)".

[0470] Example 1: OLED Manufacturing

[0471] By comparing with material combinations from the prior art, the following examples (see Tables 8 to 10) illustrate the use of the material combinations of the present invention in OLEDs.

[0472] Pretreatment of Examples V1 to V5 and E1a to E5g: Glass plates coated with 50 nm thick structured ITO (indium tin oxide) were treated with oxygen plasma before coating, followed by argon plasma treatment. These plasma-treated glass plates formed the substrate for applying OLEDs.

[0473] The OLED essentially has the following layer structure: substrate / hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / emitting layer (EML) / optional hole blocking layer (HBL) / electron transport layer (ETL) / optional electron injection layer (EIL), and finally a cathode. The cathode is formed of an aluminum layer with a thickness of 100 nm. The exact structure of the OLED can be seen in Table 8. The materials required to manufacture the OLED (if they have not been described before) are shown in Table 10. Device data for the OLED are listed in Table 9.

[0474] Examples V1 and V5 are comparative examples of using biscarbazole as the primary hole transport agent according to the prior art.

[0475] Examples E1a to E5f illustrate data for the OLED of the present invention.

[0476] All materials are applied in a vacuum chamber via thermal vapor deposition. In this case, the luminescent layer always consists of at least two matrix materials and a luminescent dopant (emitting agent), which is added to the matrix materials by co-evaporation in a specific volume ratio. Details given here, such as E13:BCbz1:TE2 (32%:60%:8%), indicate that material E13 is present in the layer at a volume ratio of 32%, BCbz1 at 60%, and TE2 at 8%. Similarly, the electron transport layer can also consist of a mixture of two materials.

[0477] Electroluminescence spectrum at 1000 cd / m 2 The luminous density was measured, and the CIE 1931 x and y color coordinates were calculated accordingly. Parameter U10 in Table 9 refers to a current density of 10 mA / cm². 2 The required voltage. SE10 and EQE10 represent the voltage required at 10mA / m. 2 The current efficiency and external quantum efficiency achieved at that time.

[0478] Lifetime LD is defined as the period during which a device operates at a constant current density j0 while maintaining a current density of cd / m². 2 The value is the time it takes for the luminous density, measured in the positive direction, to decrease from the initial luminous density to a specific percentage L1. The figure L1 = 80% in Table 9 indicates that the lifetime reported in the LD column corresponds to a value in cd / m³. 2 The time it takes for the calculated luminous density to drop to 80% of its initial value.

[0479] Use of the mixture of the present invention in OLEDs

[0480] The material combinations of the present invention are used as matrix materials in the emissive layer of green phosphorescent OLEDs in Examples E1a-k, E2a-h, E3a-g, E4a-j, and E5a-g. In comparison with the prior art, materials E7, E8, E13, E15, E18, and BCbz1 to BCbz5 are used in Examples V1 to V5.

[0481] When comparing the inventive examples with the corresponding comparative examples, it is clear that the inventive examples each show a significant advantage in terms of device lifetime, while other performance data of OLEDs are comparable.

[0482] Table 8: Structure of OLED

[0483]

[0484]

[0485]

[0486] Table 9: OLED Data

[0487]

[0488]

[0489] Table 10: Structural formulas of the OLED materials used (if not previously described):

[0490]

[0491]

[0492] Unless otherwise specified, the following synthesis was carried out in a dry solvent under a protective atmosphere. Solvents and reagents may be purchased from, for example, Sigma-Aldrich or ABCR. The corresponding numbers in square brackets or the numbers cited for individual compounds relate to the CAS numbers of the compounds known from the literature.

[0493] S1a:

[0494]

[0495] 2-(8-chlorodibenzofuran-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxane[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 inert for 30 min. Then, tri-o-tolylphosphine (913 mg, 3.0 mmol) was added, followed by palladium(II) acetate (112 mg, 0.5 mmol), and the reaction mixture was heated under reflux for 20 h. After cooling, the precipitated solid was filtered off and washed with ethanol. The crude product was recrystallized from m-xylene. Yield: 46.11 g (88 mmol, 88%) of solid, 98% according to HPLC.

[0496] The following compounds can be prepared similarly: purification can be performed using column chromatography, or using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, and 1,4-diethyl-2-ethylhexylene. Recrystallization was performed using alkanes, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.

[0497]

[0498]

[0499] S1b:

[0500]

[0501] S1a (46.11 g, 88.0 mmol), bis(pinacolyl)diborane [73183-34-3] (25.39 g, 100.0 mmol) and potassium acetate (28.82 g, 293.6 mmol) were prepared in a 1,4-didioxanone atmosphere. The initial feed in alkane (700 ml) was inertized with argon for 2 min. Subsequently, XPhos [564483-18-7] (456 mg, 0.96 mmol) and Pd2(dba)3 [51364-51-3] (435 mg, 0.48 mmol) were added, and the reaction mixture was stirred under reflux for 26 h. After cooling, the solvent was removed by rotary evaporation, and the residue was treated by extraction with toluene / water. The organic phase was dried over Na2SO4 and concentrated to dryness by rotary evaporation. The residue was boiled with ethyl acetate under reflux for 2 h, and the solid was filtered off and washed with ethyl acetate. Yield: 49.4 g (80.2 mmol, 91%) of solid; according to 1 The H NMR value was 97%.

[0502] The following compounds can be prepared similarly: instead of X-Phos, S-Phos or tricyclohexylphosphine can be used as ligands, or Pd(dppf)Cl2 x CH2Cl2 [95464-05-4] can be used for the boronization of the brominated functional groups. Purification can be performed using column chromatography, or using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-di(2 ... Recrystallization was performed using alkanes, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.

[0503]

[0504]

[0505]

[0506] S1c:

[0507]

[0508] 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 initially charged into 1000 mL of o-xylene. Subsequently, tri-tert-butylphosphine [13716-12-6] (1 mol / L toluene solution, 5.0 mL, 5.0 mmol) and tris(dibenzylideneacetone)palladium [51364-51-3] (1.14 g, 1.25 mmol) were added sequentially, and the reaction mixture was heated under reflux for 16 hours. The reaction mixture was cooled to room temperature and treated by extraction with toluene / water. The organic phases were combined and dried over Na2SO4, and the solvent was removed under reduced pressure using a rotary evaporator. The obtained solid was suspended in 300 ml of ethanol, refluxed and stirred for 1 hour, and then filtered. The crude product was recrystallized from ethyl acetate. Yield: 28.4 g (64 mmol, 48%) of solid, based on 1 The HNMR value was 98%.

[0509] The following compounds can be prepared similarly: purification can be performed using column chromatography, or using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, and 1,4-diethyl-2-ethylhexylene. Recrystallization was performed using alkanes, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.

[0510]

[0511] S1d:

[0512]

[0513] Under an inert atmosphere, the initial feed of 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), cuprous iodide (3.81 g, 20.0 mmol), and 1,3-bis(2-pyridyl)propane-1,3-dione (4.52 g, 20.0 mmol) in DMF (350 ml) was inertized with argon for 15 minutes, and then stirred at 115 °C for 32 hours. The mixture was cooled to room temperature, filtered through a diatomaceous earth bed, and washed twice thoroughly with 200 ml of DMF. The filtrate was then concentrated to dryness using a rotary evaporator. The residue was treated by dichloromethane / water extraction, and the organic phase was washed twice with water and once with saturated NaCl solution and dried over Na₂SO₄. 150 mL of ethanol was added, and the dichloromethane was withdrawn to 500 mbar on a rotary evaporator. The precipitated solid was filtered off and washed with ethanol. Yield: 24.71 g (50.6 mmol, 51%) of a gray solid; according to 1 The H NMR value is 95%.

[0514] The following compounds can be prepared similarly: purification can be performed using column chromatography, or using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, and 1,4-diethyl-2-ethylhexylene. Recrystallization was performed using alkanes, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.

[0515]

[0516] S1e:

[0517]

[0518] Toluene (500 mL) and water (150 mL) were added to the initial feed of 8-bromodibenzofuran-1-yl trifluoromethanesulfonic acid [2247123-46-0] (47.00 g, 118.9 mmol), 4,4,5,5-tetramethyl-2-(2-benzophenanthrene)-1,3,2-dioxane (49.72 g, 140.4 mmol), and K₂CO₃ (32.88 g, 237.9 mmol) in a flask, and the mixture was inert with argon for 30 min. Subsequently, 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 h. After cooling, the precipitated solid was filtered off and washed twice with ethanol. The crude product was extracted by reflux and stirring in ethanol for 2 hours, and the solid was filtered off after cooling. Yield: 58.8 g (108 mmol, 91%) of solid; according to 1 The purity of H NMR is 98%.

[0519] The following compounds can be prepared similarly: purification can be performed using column chromatography, or using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, and 1,4-diethyl-2-ethylhexylene. Recrystallization was performed using alkanes, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.

[0520]

[0521]

[0522]

[0523] Preparation of compounds

[0524] E1 synthesis:

[0525]

[0526] Tetrahydrofuran (200 mL) and water (50 mL) were added to the initial feed of 2,4-diphenyl-6-[8-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-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, and the mixture was inert with argon for 30 min. Subsequently, 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 h. After cooling, the precipitated solid was filtered off and washed twice with water and twice with ethanol. The crude product was thermally extracted three times with toluene / heptane (1:1), recrystallized three times from toluene, and finally sublimated under high vacuum. Yield: 14.8 g (18.7 mmol, 67%); Purity: >99.9% (according to HPLC).

[0527] The following compounds can be prepared similarly: the catalyst system (palladium source and ligand) used here can also be Pd2(dba)3 with SPhos [657408-07-6] or bis(triphenylphosphine)palladium(II) chloride [13965-03-2]. Column chromatography or other standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, and 1,4-diethyl-2-ethylhexyl chloride can also be used. Purification can be achieved by recrystallization or thermal extraction of alkanes, or by recrystallization using high-boiling-point compounds such as dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0528]

[0529]

[0530]

[0531]

[0532]

[0533]

[0534]

[0535]

[0536] E20:

[0537]

[0538] Toluene (300 ml) and water (100 ml) were added to an initial feed of 2,4-diphenyl-6-[8-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-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, and the mixture was inert with argon for 30 min. Subsequently, tetra(triphenylphosphine)palladium(0) [14221-01-3] (1.00 g, 0.87 mmol) was added, and the mixture was heated under reflux for 36 h. After cooling, the reaction mixture was treated by extraction with toluene and water, the combined organic phases were dried over Na2SO4, and the filtrate was concentrated to dryness by rotary evaporation. The residue was suspended in 350 mL of hot EtOH and stirred under reflux for 1 hour. After cooling, the solid was filtered off. The crude product was extracted twice with toluene / heptane (1:1), recrystallized three times from n-butyl acetate, and finally sublimed under high vacuum. Yield: 14.8 g (18.7 mmol, 67%); Purity: >99.9% (according to HPLC).

[0539] The following compounds can be prepared similarly: the catalyst system used here, instead of tetra(triphenylphosphine)palladium(0), can also be Pd2(dba)3 with SPhos [657408-07-6] (palladium source and ligand) or bis(triphenylphosphine)palladium(II) chloride [13965-03-2]. Column chromatography or other standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, and 1,4-diethyl-2-ethylhexyl chloride can also be used. Purification can be achieved by recrystallization or thermal extraction of alkanes, or by recrystallization using high-boiling-point compounds such as dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0540]

[0541]

[0542]

[0543] H3

[0544]

[0545] Under an inert atmosphere, 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-dioxacyclopentaborane-2-yl)indolo[3,2,1-jk]carbazole (51.1 g, 147.3 mmol) [CAS-1454807-26-1] were reacted with toluene (1200 ml) and 1,4-dioxacyclopentaborane-2-yl)indo ...intoluene (1200 ml) and 1,4-dioxacyclopentaborane-2-yl)indo[3,2,1-jk]carbazole (51.1 g, 147.3 mmol) [CAS-1454807-26-1]intoluene (1200 ml) and 1,4-dioxacyclopentaborane-2-yl)indo[3,2,1-jk]carbazole (51.1 g, 147.3 mmol) [CAS-1454807-26-1]indo[3,2,1-jk]carbazole (51.1 g, 147.3 mmol) [CAS-1454807-26-1 K₃PO₄ (95.7 g, 451 mmol), tris(o-tolyl)phosphine (2.33 g, 7.52 mmol), and Pd(OAc)₂ (840 mg, 3.76 mmol) were added to an initial feed of alkane (1200 ml) and water (600 ml), and the mixture was stirred under reflux for 32 hours. After cooling, the mixture was treated by toluene / water extraction, with the aqueous phase extracted three times with toluene (500 ml each time), and the combined organic phases dried over Na₂SO₄. The crude product was first extracted by stirring in EtOH (1500 ml). The filtered solid was extracted twice with hot heptane / toluene, recrystallized twice from DMAc, and finally sublimated under high vacuum.

[0546] Yield: 40.5 g (72.5 mmol, 48%); Purity: >99.9% (according to HPLC).

[0547] The following compounds can be prepared similarly: the catalyst system (palladium source and ligand) used here can also be Pd2(dba)3 with SPhos [657408-07-6], or tetra(triphenylphosphine)palladium(0) or bis(triphenylphosphine)palladium(II) chloride [13965-03-2]. Column chromatography or other standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-di(diphenylphosphine) chloride, etc., can also be used. Purification can be achieved by recrystallization or thermal extraction of alkanes, or by recrystallization using high-boiling-point compounds such as dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0548]

[0549]

[0550]

[0551]

[0552]

Claims

1. An organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode and at least one organic layer, the at least one organic layer containing at least one light-emitting layer, wherein the at least one light-emitting layer contains at least one compound of formula (1) as host material 1 and at least one compound of formula (2) as host material 2. Equation (1) Equation (2) The symbols and markings used are as follows: X is the same or different in every case and is CR. 0 Or N, where at least one symbol X is N; X2 is the same or different in each case and is CH, CR 1 Or N, where no more than two symbols X2 can be N; Y and Y1 are the same or different in each case and are selected from O and S; L may be the same or different in each case and is a single bond or an aromatic ring system with 6 to 30 aromatic ring atoms; L1 may be the same or different in each case and is a single bond or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms; R 0 In each case, it is independently an aromatic ring system with 6 to 18 carbon atoms, consisting of H, D, or unsubstituted, partially deuterated, or fully deuterated carbon atoms. R In each case, it is independently a D or an aromatic or heteroaromatic ring system having 6 to 18 carbon atoms and being partially or fully deuterated; R may be the same or different in each case and is selected from CN groups, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 10 to 40 aromatic ring atoms, wherein the aromatic ring system and the heteroaromatic ring system may be represented by one or more R groups. 2 Group substitution and wherein, when the heteroaromatic ring system contains a nitrogen atom, the heteroaromatic ring system is via N-bonding; R 1 In each case, the same or different and selected from CN, are straight-chain alkyl, alkoxy, or thioalkyl groups having 1 to 20 carbon atoms, or branched or cyclic alkyl, alkoxy, or thioalkyl groups having 3 to 20 carbon atoms, aromatic or heteroaromatic ring systems having 5 to 40 aromatic ring atoms, or aryloxy or heteroaryloxy groups having 5 to 40 aromatic ring atoms, or aralkyl or heteroarylalkyl groups having 5 to 40 aromatic ring atoms; and simultaneously, two substituents R bonded to the same carbon atom or to adjacent carbon atoms. 1 It can form monocyclic or polycyclic aliphatic, aromatic, or heterocyclic ring systems, which can be formed by one or more R... 2 Group substitution; R 2 In each case, they may be the same or different and are selected from 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 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 substituted by one or more R 3 Group substitution, wherein one or more non-adjacent CH2 groups can be replaced 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 The hydrogen atoms can be replaced by D, F, Cl, Br, I, CN, or NO2, and the ring has 5 to 60 aromatic ring atoms, and in each case can be replaced by one or more R atoms. 3 Aromatic or heteroaromatic ring systems with substituted groups, having 5 to 60 aromatic ring atoms and capable of being substituted by one or more R groups. 3 A group-substituted aryloxy or heteroaryloxy group, or a combination of these systems, wherein two or more adjacent substituents R 2 Optionally, a single-ring or multi-ring aliphatic, aromatic, or heteroaromatic ring system can be formed, wherein the aliphatic, aromatic, or heteroaromatic ring system can be formed by one or more R 3 Group substitution; R 3 In each case, the same or different aliphatic hydrocarbon group selected from H, D, F, CN, having 1 to 20 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, wherein one or more hydrogen atoms can be replaced by D, F, Cl, Br, I, or CN, and the aliphatic hydrocarbon group and the aromatic or heteroaromatic ring system can be replaced by one or more alkyl groups each having 1 to 4 carbon atoms; simultaneously, two or more adjacent R 3 Substituents can together form monocyclic or polycyclic aliphatic ring systems; Ar1 is the same or different in each case and has 5 to 30 aromatic ring atoms and can be separated by one or more non-aromatic R atoms. 3 Aromatic or heteroaromatic ring systems with substituted groups; simultaneously, two Ar1 groups bonded to the same nitrogen, phosphorus, or boron atom can also be bonded via a single bond or selected from N(R) 3 ), C(R 3 2. The bridge bases of O and S are connected to each other; Ar2 and Ar3, in each case independently, are aromatic ring atoms with 5 to 40 atoms and can be separated by one or more R atoms. 2 A substituted aryl or heteroaryl group; A is independently a group of formula (3) or (4) in each case. Equations (3) and (4); Ar is, in each case, independently an aryl group having 6 to 40 aromatic ring atoms that can be substituted by one or more R# groups, or a heteroaryl group having 5 to 40 aromatic ring atoms that can be substituted by one or more R# groups; In formula (3) or (4) Indicates the binding site with the formula (2); R# is the same or different in each case and is selected from 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 generated by one or more R 2 Group substitution, wherein one or more non-adjacent CH2 groups can be replaced 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 The hydrogen atoms can be replaced by D, F, Cl, Br, I, CN, or NO2, and the ring has 5 to 40 aromatic ring atoms, and in each case can be replaced by one or more R atoms. 2 Aromatic or heteroaromatic ring systems with substituted groups, having 5 to 40 aromatic ring atoms and capable of being substituted by one or more R groups. 2 A group-substituted aryloxy or heteroaryloxy group, or having 5 to 40 aromatic ring atoms and capable of being substituted by one or more R groups. 2 A group-substituted aralkyl or heteroaralkyl group; a, b, and c are each independently 0 or 1 in each case, and the sum of the symbols is 1 in each case a+b+c; m and o are independently 0, 1, 2, 3 or 4 in each case; n and p are each independently 0, 1, 2, or 3 in each case; and q, r, s, and t are each independently 0 or 1 in each case.

2. The organic electroluminescent device according to claim 1, characterized in that... The symbol Y in main material 1 is O.

3. The organic electroluminescent device according to claim 1 or 2, characterized in that... Main material 2 conforms to one of formulas (2a), (2b) or (2c). Equation (2a), Equation (2b), Equation (2c), The symbols and markings used are A, R 1 q, r, and s are as defined in claim 1.

4. The organic electroluminescent device according to claim 1 or 2, characterized in that, In the main material 1, X is N in two cases or N in three cases.

5. The organic electroluminescent device according to claim 1 or 2, characterized in that... It is an electroluminescent device selected from organic light-emitting transistors, organic quenching devices, organic light-emitting electrochemical cells, organic laser diodes, and organic light-emitting diodes.

6. The organic electroluminescent device according to claim 1 or 2, characterized in that, In addition to the light-emitting layer (EML), the organic electroluminescent device also includes 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. The organic electroluminescent device according to claim 1 or 2, characterized in that, In addition to the at least one host material 1 and the at least one host material 2, the light-emitting layer also contains at least one phosphorescent material.

8. The organic electroluminescent device according to claim 7, characterized in that... The phosphorescent emitter conforms to formula (III). Equation (III) The symbols and notations for equation (III) are defined as follows: When 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.

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

10. The method according to claim 9, characterized in that... The light-emitting layer is formed by depositing the compound of at least one formula (1) and the compound of at least one formula (2) continuously or simultaneously from at least two material sources in the gas phase, or characterized in that the light-emitting layer is formed by depositing the compound of at least one formula (1) and the compound of at least one formula (2) together with the at least one phosphorescent material from at least two material sources in the gas phase.

11. The method according to claim 9, characterized in that... The compound of at least one formula (1) and the compound of at least one formula (2) are deposited as a mixture with the at least one phosphorescent material from the gas phase continuously or simultaneously to form the luminescent layer.

12. The method according to claim 9, characterized in that... The compound of at least one formula (1) and the compound of at least one formula (2) are applied from the solution together with the at least one phosphorescent material to form the luminescent layer.

13. A mixture comprising at least one compound of formula (1) as a main material 1 and at least one compound of formula (2) as a main material 2. Equation (1) Equation (2) The symbols and markings used are as follows: X is the same or different in every case and is CR. 0 Or N, where at least one symbol X is N; X2 is the same or different in each case and is CH, CR 1 Or N, where no more than two symbols X2 can be N; Y and Y1 are the same or different in each case and are selected from O and S; L may be the same or different in each case and is a single bond or an aromatic ring system with 6 to 30 aromatic ring atoms; L1 may be the same or different in each case and is a single bond or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms; R 0 In each case, it is independently an aromatic ring system with 6 to 18 carbon atoms, consisting of H, D, or unsubstituted, partially deuterated, or fully deuterated carbon atoms. R In each case, it is independently a D or an aromatic or heteroaromatic ring system having 6 to 18 carbon atoms and being partially or fully deuterated; R may be the same or different in each case and is selected from CN groups, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 10 to 40 aromatic ring atoms, wherein the aromatic ring system and the heteroaromatic ring system may be represented by one or more R groups. 2 Group substitution and wherein, when the heteroaromatic ring system contains a nitrogen atom, the heteroaromatic ring system is via N-bonding; R 1 In each case, the same or different and selected from CN, are straight-chain alkyl, alkoxy, or thioalkyl groups having 1 to 20 carbon atoms, or branched or cyclic alkyl, alkoxy, or thioalkyl groups having 3 to 20 carbon atoms, aromatic or heteroaromatic ring systems having 5 to 40 aromatic ring atoms, or aryloxy or heteroaryloxy groups having 5 to 40 aromatic ring atoms, or aralkyl or heteroarylalkyl groups having 5 to 40 aromatic ring atoms; and simultaneously, two substituents R bonded to the same carbon atom or to adjacent carbon atoms. 1 It can form monocyclic or polycyclic aliphatic, aromatic, or heterocyclic ring systems, which can be formed by one or more R... 2 Group substitution; R 2 In each case, they may be the same or different and are selected from 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 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 substituted by one or more R 3 Group substitution, wherein one or more non-adjacent CH2 groups can be replaced 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 The hydrogen atoms can be replaced by D, F, Cl, Br, I, CN, or NO2, and the ring has 5 to 60 aromatic ring atoms, and in each case can be replaced by one or more R atoms. 3 Aromatic or heteroaromatic ring systems with substituted groups, having 5 to 60 aromatic ring atoms and capable of being substituted by one or more R groups. 3 A group-substituted aryloxy or heteroaryloxy group, or a combination of these systems, wherein two or more adjacent substituents R 2 Optionally, a single-ring or multi-ring aliphatic, aromatic, or heteroaromatic ring system can be formed, wherein the aliphatic, aromatic, or heteroaromatic ring system can be formed by one or more R 3 Group substitution; R 3 In each case, the same or different aliphatic hydrocarbon group selected from H, D, F, CN, having 1 to 20 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, wherein one or more hydrogen atoms can be replaced by D, F, Cl, Br, I, or CN, and the aliphatic hydrocarbon group and the aromatic or heteroaromatic ring system can be replaced by one or more alkyl groups each having 1 to 4 carbon atoms; simultaneously, two or more adjacent R 3 Substituents can together form monocyclic or polycyclic aliphatic ring systems; Ar1 is the same or different in each case and has 5 to 30 aromatic ring atoms and can be separated by one or more non-aromatic R atoms. 3 Aromatic or heteroaromatic ring systems with substituted groups; simultaneously, two Ar1 groups bonded to the same nitrogen, phosphorus, or boron atom can also be bonded via a single bond or selected from N(R) 3 ), C(R 3 2. The bridge bases of O and S are connected to each other; Ar2 and Ar3, in each case independently, are aromatic ring atoms with 5 to 40 atoms and can be separated by one or more R atoms. 2 A substituted aryl or heteroaryl group; A is independently a group of formula (3) or (4) in each case. Equations (3) and (4); Ar is, in each case, independently an aryl group having 6 to 40 aromatic ring atoms that can be substituted by one or more R# groups, or a heteroaryl group having 5 to 40 aromatic ring atoms that can be substituted by one or more R# groups; In formula (3) or (4) Indicates the binding site with the formula (2); R# is the same or different in each case and is selected from 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 generated by one or more R 2 Group substitution, wherein one or more non-adjacent CH2 groups can be replaced 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 The hydrogen atoms can be replaced by D, F, Cl, Br, I, CN, or NO2, and the ring has 5 to 40 aromatic ring atoms, and in each case can be replaced by one or more R atoms. 2 Aromatic or heteroaromatic ring systems with substituted groups, having 5 to 40 aromatic ring atoms and capable of being substituted by one or more R groups. 2 A group-substituted aryloxy or heteroaryloxy group, or having 5 to 40 aromatic ring atoms and capable of being substituted by one or more R groups. 2 A group-substituted aralkyl or heteroaralkyl group; a, b, and c are each independently 0 or 1 in each case, and the sum of the symbols is 1 in each case a+b+c; m and o are independently 0, 1, 2, 3 or 4 in each case; n and p are each independently 0, 1, 2, or 3 in each case; and q, r, s, and t are each independently 0 or 1 in each case.

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. A formulation comprising the mixture according to claim 13 or 14 and at least one solvent.

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