Organic electroluminescent device

Abstract

The present invention relates to an organic electroluminescent device comprising a light-emitting layer containing an electron-transporting host material and a hole-transporting host material, and to a formulation containing a mixture of said host materials and to a mixture containing said host materials. The electron-transporting host material corresponds to a compound of formula (1) containing a diazadibenzofuran unit or a diazadibenzothiophene unit. The hole-transporting host material corresponds to a compound of formula (2) from the category of bis-carbazoles or derivatives thereof.

Description

Technical Field

[0001] This invention relates to an organic electroluminescent device comprising a light-emitting layer containing an electron transport host material and a hole transport host material, and to formulations comprising a mixture of the host materials and mixtures comprising the host materials. The electron transport host material corresponds to a compound of formula (1), which comprises a diazadibenzofuran or a diazadibenzothiophene unit. The hole transport host material corresponds to a compound of formula (2) from the bicarbazole class or derivatives thereof. Background Technology

[0002] The structures of organic electroluminescent devices (such as OLEDs – organic light-emitting diodes or OLECs – organic light-emitting electrochemical cells) where organic semiconductors are used as functional materials are well-known. In addition to phosphorescent emitters, the luminescent materials used here are increasingly phosphorescent rather than fluorescent organometallic complexes. However, in general, improvements are still needed in OLEDs, especially in OLEDs exhibiting triplet emission (phosphorescence), in aspects such as efficiency, operating voltage, and lifetime.

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

[0004] Those skilled in the art are familiar with host materials used in organic electronic devices. The term "matrix material" is also frequently used in the prior art when referring to a host material for phosphorescent emitters. This usage of the term also applies to the present invention. Meanwhile, various host materials for fluorescent and phosphorescent electronic devices have been developed.

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

[0006] US 6,392,250 B1 discloses the use of a mixture of an electron transport material, a hole transport material, and a phosphor in the emissive layer of an OLED. This mixture improves the lifetime of the OLED compared to existing technologies.

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

[0008] WO15037675 discloses benzothiophene-pyrimidine compounds and their use as electron transport materials in organic electroluminescent devices.

[0009] WO2015105315 and WO2015105316 disclose heterocyclic compounds containing two nitrogen atoms and their use as host materials in organic electroluminescent devices, optionally in combination with another host material.

[0010] US2015207082 describes azidobenzofuran compounds and diazidobenzofuran compounds, as well as azidobenzothiophene compounds and diazidobenzothiophene compounds, and their use in organic electroluminescent devices, particularly as electron transport materials.

[0011] US2016013421 discloses benzothiophene-pyrimidine compounds and their use as host materials in organic electroluminescent devices.

[0012] US2016072078 describes an electron transport host material containing carbazole units.

[0013] US2017200903 describes diazadibenzofuran compounds and diazadibenzothiophene compounds and their use in organic electroluminescent devices, particularly as electron transport materials.

[0014] KR1020160046077 and KR102016004678 describe an organic light-emitting device comprising a light-emitting layer containing a special light-emitting body combined with various host materials.

[0015] US2017186971 describes benzothiophene-pyrimidine compounds and benzofuran-pyrimidine compounds and their use as host materials in organic electroluminescent devices, wherein each of the benzothiophene-pyrimidine compounds and benzofuran-pyrimidine compounds has two substituents comprising furan, thiophene, or pyrrole units.

[0016] WO17186760 discloses diazacarbazole compounds and their uses in organic electroluminescent devices as host materials, electron transport materials, and hole blocking materials.

[0017] WO18060218 discloses diazadibenzofuran compounds and diazadibenzothiophene compounds and their use in organic electroluminescent devices, wherein the benzothiophene pyrimidine compound and the benzofuran pyrimidine compound each have at least one substituent comprising a carbazole unit.

[0018] WO18060307 describes diazadibenzofuran compounds and diazadibenzothiophene compounds and their use in organic electroluminescent devices.

[0019] WO18088665 describes compounds having triphenylide substituents, said triphenylide substituents being bis-substituted with phenyl groups and having another substituent containing an electron transport group, and the use of said compounds in organic electroluminescent devices.

[0020] WO18234926, WO18234932, WO19059577, WO19058200 and WO19229584 describe diazoxide dibenzofuran and diazoxide dibenzothiophene derivatives that can be used as host materials in electroluminescent devices.

[0021] WO20067657 describes a material composition and its use in optoelectronic devices.

[0022] However, improvements are still needed, both when using these materials and when using mixtures of these materials, particularly in terms of the efficiency, operating voltage, and / or lifetime of organic electroluminescent devices.

[0023] Therefore, the problem solved by the present invention is to provide a combination of host materials and to provide a corresponding electroluminescent device, the combination being suitable for use in organic electroluminescent devices, especially in fluorescent or phosphorescent OLEDs, and resulting in good device properties, particularly in terms of improved lifetime. Summary of the Invention

[0024] 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 transport compound of formula (2) as a second host material in the emitting layer of an organic electroluminescent device. The use of such a material combination in the fabrication of the emitting layer in an organic electroluminescent device results in these devices exhibiting very good properties, particularly in terms of lifetime, especially with the same or improved efficiency and / or operating voltage. These advantages are particularly evident in the presence of the emitting component in the emitting layer, especially in combination with a emitting element of formula (3) or formulas (I) to (VI) at a concentration of 2 to 15 wt%, or in combination with a monoamine of formula (4) in the hole injection layer and / or hole transport layer.

[0025] Therefore, the present invention first provides an organic electroluminescent device, which includes an anode, a cathode, and at least one organic layer containing at least one light-emitting layer, wherein the at least one light-emitting layer contains at least one compound of formula (1) as host material 1 and at least one compound of formula (2) as host material 2.

[0026]

[0027] The symbols and markings used are as follows:

[0028] Y is independently N or [L] in each case. n -Ar2 or [L]-R * Where exactly two Ys are N and are bonded by at least one [L]-R group * Or [L] n Separated by -Ar2;

[0029] V is either O or S;

[0030] Rx is [L] n -Ar2 or [L]-R * ;

[0031] R * It is a triphenylidene group, which can be substituented by exactly one R group. # Substitution and / or substitution by one or more groups R;

[0032] The condition is that the substituent [L]-R * It appears exactly once in the compound of formula (1);

[0033] n is 0 or 1;

[0034] m is 0 or 1;

[0035] L is independently the same or different in each case and represents an aryl group, a divalent dibenzofuran group or a divalent dibenzothiophene group having 6 to 20 carbon atoms, each of which may be substituted by one or more groups R;

[0036] Ar2 may be the same or different in each case and represents an aromatic ring system having 6 to 30 ring atoms that can be substituted by one or more groups R;

[0037] R may be the same or different in each case and is selected from D, F, CN, a straight-chain alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, wherein one or more non-adjacent CH2 groups may be R 2 C = CR 2The hydrogen atoms can be replaced by O or S, and one or more of the hydrogen atoms can be replaced by D, F or CN;

[0038] R# is an aryl group having 6 to 20 carbon atoms, said aryl group may be replaced by one or more groups R;

[0039] R 2 In each case, the same or different and selected from H, D, F, CN, straight-chain alkyl groups having 1 to 20 carbon atoms or branched or cyclic alkyl groups having 3 to 20 carbon atoms, wherein one or more non-adjacent CH2 groups may be replaced by O or S and wherein one or more hydrogen atoms may be replaced by D, F or CN.

[0040] K, M: When x and y are 0 and when x1 and y1 are 0, K and M are independently unsubstituted or partially or fully deuterated or R having 6 to 40 ring atoms. * - Monosubstituted aromatic ring systems, or

[0041] K, M: As long as the values ​​of x, x1, y and / or y1 are 1, then K and M are independently related to X or X 1 Together they form a heteroaromatic ring system with 14 to 40 ring atoms;

[0042] x and x1 are each 0 or 1 independently in each case;

[0043] y and y1 are each 0 or 1 independently in each case;

[0044] X and X 1 In each case, it is independently a bond or C(R) + )2;

[0045] R 0 In each case, it is independently an unsubstituted or partially or fully deuterated aromatic ring system having 6 to 18 ring atoms;

[0046] R + In each case, it is independently a straight-chain or branched alkyl group having 1 to 4 carbon atoms, and

[0047] c, d, e, and f are independently 0 or 1.

[0048] The present invention further provides a method for manufacturing an organic electroluminescent device, as well as mixtures comprising at least one compound of formula (1) and at least one compound of formula (2), specific combinations of materials, and formulations containing such mixtures or combinations of materials. The corresponding preferred embodiments described below also constitute part of the subject matter of the present invention. The surprising and advantageous effects are obtained by specifically selecting compounds of formula (1) and compounds of formula (2). The surprising and advantageous effects are obtained by specifically selecting compounds of formula (1) and compounds of formula (2) in addition to specific emitters in the light-emitting layer and specific monoamines in the hole injection and / or hole transport layer. Detailed Implementation

[0049] The organic electroluminescent device of the present invention is, for example, an organic light-emitting transistor (OLET), an organic field quenching device (OFQD), an organic light-emitting electrochemical cell (OLEC, LEC, LEEC), an organic laser diode (O-laser), or an organic light-emitting diode (OLED). The organic electroluminescent device of the present invention is particularly an organic light-emitting diode or an organic light-emitting electrochemical cell. The device of the present invention is more preferably an OLED.

[0050] As described in the context, the organic layer of the device of the present invention comprises a light-emitting layer containing a material combination of at least one compound of formula (1) and at least one compound of formula (2), and preferably further comprises, 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 comprise multiple layers selected from EML, HIL, HTL, ETL, EIL, and HBL.

[0051] However, the device may also contain inorganic materials or layers formed entirely of inorganic materials.

[0052] Preferably, the organic layer of the device of the present invention comprises a hole injection layer and / or a hole transport layer of a monoamine that does not contain carbazole units, wherein the hole injection material and the hole transport material are both a hole injection layer and a hole transport layer. Suitable choices of monoamine compounds and preferred monoamines are described below.

[0053] Preferably, the luminescent layer comprising at least one compound of formula (1) and at least one compound of formula (2) is a phosphorescent layer, characterized in that, in addition to the host material combination comprising the compounds of formula (1) and formula (2) as described above, it also comprises at least one phosphorescent emitter. Suitable selection of the emitter and preferably the emitter is described below.

[0054] In the context of this invention, the aryl group contains 6 to 40 aromatic ring atoms, preferably carbon atoms. The heteroaryl group in the context of this invention contains 5 to 40 aromatic ring atoms, wherein the ring atoms comprise carbon atoms and at least one heteroatom, provided that the total number of carbon atoms and heteroatoms is at least 5. The heteroatom is preferably selected from N, O, and / or S. The aryl group or heteroaryl group is understood herein to refer to a simple aromatic ring, i.e., phenyl, derived from benzene; or a simple heteroaryl ring, for example, derived from pyridine, pyrimidine, or thiophene; or a fused aryl or heteroaryl group, for example, derived from naphthalene, anthracene, phenanthrene, quinoline, or isoquinoline. Therefore, an aryl group having 6 to 18 carbon atoms is preferably phenyl, naphthyl, or phenanthrene, without limitation on the aryl group as a substituent. The aryl or heteroaryl group in the context of this invention may contain one or more substituents R, wherein the substituents R are as described below.

[0055] The aromatic ring systems in the context of this invention contain 6 to 40 ring atoms. These aromatic ring systems also include aryl groups as described above.

[0056] Aromatic ring systems having 6 to 18 carbon atoms as ring atoms are preferably selected from phenyl, biphenyl, naphthyl, and phenanthrene.

[0057] The heteroaromatic ring systems in the context of this invention 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 systems also include heteroaryl groups as described above. The heteroatoms in the heteroaromatic ring systems are preferably selected from N, O, and / or S.

[0058] 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 may 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. Therefore, for example, 9,9'-spirodifluorene, 9,9-diarylfluorene, triarylamines, diaryl ethers, piracene, etc., should also be considered aromatic or heteroaromatic ring systems in the sense of this invention, as should systems in which two or more aryl groups are interrupted by, for example, straight-chain or cyclic alkyl groups or by silyl groups. Additionally, 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 included within the definition of aromatic or heteroaromatic ring systems.

[0059] The abbreviation Ar2 is independently the same or different in each case and represents an aromatic ring system having 6 to 30 carbon atoms, which may be substituted by one or more groups R, wherein the groups R are defined as described in the context.

[0060] In the context of this invention, cyclic alkyl groups are understood to refer to monocyclic, bicyclic, or polycyclic groups.

[0061] In the context of this invention, straight-chain, branched, or cyclic C1- to C1- are... 20 -alkyl groups are 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-di Methyl-n-octyl-1-yl, 1,1-dimethyl-n-decyl-1-yl, 1,1-dimethyl-n-dodecyl-1-yl, 1,1-dimethyl-n-tetradecyl-1-yl, 1,1-dimethyl-n-hexadecyl-1-yl, 1,1-dimethyl-n-octadecyl-1-yl, 1,1-diethyl-n-hexyl-1-yl, 1,1-diethyl-n-heptyl-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.

[0062] When a host material comprising at least one compound of formula (1) as described above or below as preferred and at least one compound of formula (2) as described in the context is used in a phosphorescent emitter, it is preferable that its triplet energy is not significantly lower than that of the phosphorescent emitter. Regarding the triplet energy level, it is preferred that T1(emitter) – 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 host material of the host material, and this condition applies to each of the two matrix materials, and T1(emitter) is the triplet energy level of the phosphorescent emitter. If the host material contains more than two matrix materials, the above relationship preferably also applies to each of the other matrix materials.

[0063] 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.

[0064] In the compounds of formula (1), Y is independently N, [L] in each case. n -Ar2 or [L]-R * Where exactly two Ys are N and are bonded by at least one [L]-R group * Or [L] n -Ar2 separated, conditional on the substituent [L]-R * It appears exactly once in the compound of formula (1).

[0065] Preferred embodiments of the compounds of formula (1) are compounds of formula (1a), (1b) or (1c), wherein the positions of the two nitrogen atoms are described more specifically, and the remaining Y independently represents [L]-R. * Or [L] n -Ar2, V represent O or S and Rx represents [L] n -Ar2 or [L]-R * ,

[0066]

[0067] The condition is that the substituent [L]-R * The m and R# appear exactly once in the compounds of formulas (1a), (1b) and (1c) and are preferably the same as those defined in the context.

[0068] The present invention also provides an organic electroluminescent device as described above, wherein the host material 1 conforms to one of formulas (1a), (1b) or (1c) as described above.

[0069] The preferred compounds of formula (1) correspond to formulas (1a) and (1b).

[0070] The preferred compounds of formula (1a) correspond to formulas (1aa), (1ab), and (1ac).

[0071]

[0072] Among them, Ar2, L, n, V, m, R# and R * It has the definition given above or the definition given below as a preferred option.

[0073] The preferred compounds of formula (1b) correspond to formulas (1ba), (1bb), and (1bc).

[0074]

[0075] Among them, Ar2, L, n, V, m, R# and R * It has the definition given above or the definition given below as a preferred option.

[0076] The preferred compounds of formula (1c) correspond to formulas (1ca), (1cb), and (1cc).

[0077]

[0078] Among them, Ar2, L, n, V, m, R# and R * It has the definition given above or the definition given below as a preferred option.

[0079] The particularly preferred compounds of formula (1) correspond to formulas (1aa) and (1ba).

[0080] In the compounds of formulas (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), and (1cc), V preferably represents O.

[0081] Therefore, the present invention also provides an organic electroluminescent device as described above, wherein in the body material 1 of formula (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), or (1cc), V represents O.

[0082] In the compounds of formulas (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), and (1cc), L is independently preferably selected from groups L-1 to L-23 in each case.

[0083]

[0084] Where W represents O or S. In the connecting bases L-14 to L-23, W is preferably O.

[0085] Therefore, the present invention also provides an organic electroluminescent device as described above, wherein in the host material 1 of formula (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), or (1cc), L is independently selected from the connecting bases L-1 to L-23 in each case.

[0086] In the compounds of formulas (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), and (1cc), L is particularly preferably selected independently from groups L-2, L-3, L-7, L-8, L-15, L-16, L-20, and L-22 as described above or as preferred above.

[0087] In the compounds of formulas (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), and (1cc), L is particularly preferably selected independently from groups L-2, L-3, L-8, L-16, and L-22 as described above or as preferred above.

[0088] In the compounds of formulas (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), and (1cc), L is particularly preferably selected independently from groups L-2, L-3, L-4, and L-5 as described above or as preferred above.

[0089] In compounds of formulas (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), and (1cc), or as preferred compounds of formulas (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), and (1cc), n is preferably 0.

[0090] In compounds of formulas (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), and (1cc), or as preferred compounds of formulas (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), and (1cc), n is preferably 1.

[0091] Among the compounds of formulas (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), and (1cc), or as preferably the compounds of formulas (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), and (1cc), the compound is selected from [L]. n -Ar2 or [L]-R * The substituent Rx can be located at the 1, 2, 3 and 4 positions of diazadibenzofuran or diazadibenzothiophene.

[0092] Among the compounds of formulas (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), and (1cc), or as preferably the compounds of formulas (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), and (1cc), the compound is selected from [L]. n -Ar2 or [L]-R * The substituent Rx is preferably located at the 2, 3, and 4 positions of diazadibenzofuran or diazadibenzothiophene, particularly preferably at the 2 and 3 positions, and very particularly preferably at the 3 position. These positions are indicated accordingly in the following diagram:

[0093]

[0094] In compounds of formulas (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), and (1cc), or as compounds of the preferred formulas (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), and (1cc), Ar2 may be the same or different in each case and represents an aromatic ring system having 6 to 30 ring atoms, which may be substituted by one or more groups R.

[0095] In compounds of formulas (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), and (1cc), or as preferred compounds of formulas (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), and (1cc), R * It is a triphenylidene group, which can be substituented by exactly one R group. # Substitution and / or substitution by one or more groups R, wherein R * Preferred means that it is substituted by exactly one substituent R # A substituted or unsubstituted triphenylide group. The triphenylide group R... * The terphenylene oxide is preferably unsubstituted. The bonding of the terphenylene oxide is preferably achieved through its 2-position as shown by the dashed line below.

[0096]

[0097] In compounds of formulas (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), and (1cc), or as preferred compounds of formulas (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), and (1cc), the substituent R is independently selected from D, F, CN, a straight-chain alkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl group having 3 to 20 carbon atoms, wherein one or more non-adjacent CH2 groups may be replaced by R. 2 C = CR 2 The substituent R is replaced by O or S, and one or more hydrogen atoms therein may be replaced by D, F or CN. The substituent R is independently preferably selected from D, F, CN, a straight-chain alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein one or more hydrogen atoms of the alkyl group may be replaced by D, F or CN.

[0098] Substituent R 2 In each case, they may be the same or different, and H or D is preferred.

[0099] The substituent R# is an aryl group having 6 to 20 carbon atoms, which may be substituted by one or more groups R, wherein R is defined as described above or as preferably defined above. The substituent R# is preferably a phenyl group, which may be substituted by one or more groups R, wherein R is defined as described above or as preferably defined above. R# is preferably an unsubstituted phenyl group.

[0100] In compounds of formulas (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), and (1cc), m is 0 or 1. The substituent R# is defined as described above or as preferably stated above. In compounds of formulas (1), (1a), (1b), (1c), (1aa), (1ab), (1ac), (1ba), (1bb), (1bc), (1ca), (1cb), and (1cc), m is preferably 0.

[0101] Examples of suitable host materials of formula (1) selected according to the present invention and preferably used in combination with at least one compound of formula (2) in the electroluminescent device of the present invention are the structures given in Table 1 below.

[0102] Table 1:

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115] Other examples of compounds of formula (1) are described in the Examples section.

[0116] In the electroluminescent device of the present invention, compounds of formula (1) that are particularly suitable for use in combination with at least one compound of formula (2) are compounds E1 to E27:

[0117]

[0118]

[0119]

[0120] The preparation of compounds of formula (1) or preferred compounds in Table 1 and compounds E1 to E27 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 halogenation, preferably bromination, and subsequent organometallic coupling reactions, such as Suzuki coupling, Heck coupling, or Hartwig-Buchwald coupling.

[0121] The preparation of the precursor of the compound of formula (1) can be carried out, for example, according to the following scheme 1, wherein V, m and R# have one of the definitions described above or above as preferred.

[0122] Option 1:

[0123]

[0124] The preparation of the compound of formula (1) can be carried out according to the following schemes 2 and 3, wherein Ar2, L, R*, V, m and R# have one of the definitions described above or above as preferred and n represents 0.

[0125] Option 2:

[0126]

[0127] Option 3:

[0128]

[0129] The preparation of the compound of formula (1) can be carried out according to the following scheme 4, wherein n represents 1 in each case, L represents a phenylene group in each case, m represents 0, and Ar2, R* and L have one of the definitions described above or above as preferred.

[0130] Option 4:

[0131]

[0132] The body material 2 present in the device of the present invention and its preferred embodiments are described below. The preferred embodiments of the body material 1 of formula (1) are also applicable to the mixtures and / or formulations of the present invention.

[0133] Main material 2 is at least one compound of formula (2),

[0134]

[0135] The symbols and markings used are as follows:

[0136] K, M: When x and y are 0 and when x1 and y1 are 0, K and M are independently unsubstituted or partially or fully deuterated or R having 6 to 40 ring atoms. * - Monosubstituted aromatic ring systems, or

[0137] K, M: As long as the values ​​of x, x1, y and / or y1 are 1, then K and M are independently related to X or X 1 Together they form a heteroaromatic ring system with 14 to 40 ring atoms;

[0138] x and x1 are each 0 or 1 independently in each case;

[0139] y and y1 are each 0 or 1 independently in each case;

[0140] X and X 1 In each case, it is independently a bond or C(R) + )2;

[0141] R 0 In each case, it is independently an unsubstituted or partially or fully deuterated aromatic ring system having 6 to 18 ring atoms;

[0142] R + In each case, it is independently a straight-chain or branched alkyl group having 1 to 4 carbon atoms, and

[0143] c, d, e, and f are independently 0 or 1.

[0144] One embodiment of the present invention includes selecting a compound of formula (2) as described above for the device according to the present invention, which is used in the light-emitting layer together with the compound of formula (1) as described above or as preferably described above or together with the compounds in Table 1 or compounds E1 to E27.

[0145] A preferred embodiment of the device according to the invention includes using a compound of formula (2) in which x, y, x1, and y1 are 0 as the host material 2. The compound of formula (2) in which x, x1, y, and y1 are 0 in each case can be represented by formula (2a).

[0146]

[0147] Where R 0c, d, e, and f are as defined in the context, and

[0148] K and M are each independently unsubstituted or partially or fully deuterated or R having 6 to 40 ring atoms. * - Monosubstituted aromatic ring systems.

[0149] In the preferred compound of formula (2a), the sum of c+d+e+f is preferably 0 or 1, and R 0 If the context is defined as preferred.

[0150] In compounds of formula (2) or (2a), R 0 In each case, it is preferred, independently, to be an unsubstituted aromatic ring system having 6 to 18 ring atoms, preferably 6 to 18 carbon atoms. R 0 In each case, it is preferably phenyl, 1,3-biphenyl, 1,4-biphenyl, naphthyl, or triphenylimide, independently. 0 In each case, phenyl is particularly preferred independently.

[0151] In compounds of formula (2) or (2a), the designations c, d, e and f are particularly preferred to be 0.

[0152] In compounds of formula (2) or (2a), K and M are preferably, in each case, independently unsubstituted or partially deuterated or R having 6 to 40 ring atoms as described above. * - Monosubstituted aromatic ring systems. In compounds of formula (2) or (2a), K and M are particularly preferred independently to be phenyl, deuterated phenyl, 1,3-biphenyl, 1,4-biphenyl, terphenyl, partially deuterated terphenyl, tetraphenyl, naphthyl, fluorenyl, 9,9-diphenylfluorenyl, bisspirofluorenyl or biphenylenemethyl.

[0153] Therefore, the present invention also provides an organic electroluminescent device as described above or as preferably described above, wherein at least one compound of formula (2) corresponds to a compound of formula (2a) or a preferred embodiment of a compound of formula (2a).

[0154] A preferred embodiment of the device according to the invention includes using a compound of formula (2) in which x1 and y1 are 0, x and y are 0 or 1, and the sum of x and y is 1 or 2, as the host material 2. The compound of formula (2) in which x1 and y1 are 0, x and y are 0 or 1, and the sum of x and y is 1 or 2, can be represented by formula (2b).

[0155]

[0156] Where X, x, y, R 0 c, d, e, and f are as defined in the context.

[0157] M is an unsubstituted, partially or fully deuterated or R-type ring with 6 to 40 ring atoms. * - Monosubstituted aromatic ring systems, and

[0158] If the value of x or y is 1, or if the values ​​of x and y are both 1, then K and X together form a heteroaromatic ring system with 14 to 40 ring atoms.

[0159] In the preferred compound of formula (2b), the sum of c+d+e+f is preferably 0, 1, or 2, and R 0 As defined above or below when preferred.

[0160] In compounds of formula (2) or (2b), the designations c, d, e, and f are particularly preferably 0 or 1. In compounds of formula (2) or (2b), the designations c, d, e, and f are very particularly preferably 0. In compounds of formula (2) or (2b), the designations c, d, e, and f are very particularly preferably 1. In compounds of formula (2) or (2b), the designations c, d, e, and f are very particularly preferably 2.

[0161] In compounds of formula (2) or (2b), K preferably forms a heteroaromatic ring system when the sum of x and y is 1 or 2. In compounds of formula (2) or (2b), X is preferably a direct bond or C(CH3)2.

[0162] Preferred compounds of formula (2) or (2b) can be represented by formulas (2b-1) to (2b-6).

[0163]

[0164] Among them, M and R 0 c, d, e, and f are defined as described above or as preferably described below.

[0165] In compounds of formulas (2), (2b), (2b-1), (2b-2), (2b-3), (2b-4), (2b-5), or (2b-6), M is an unsubstituted or partially deuterated compound having 6 to 40 ring atoms as described above, or R * - Monosubstituted aromatic ring systems. In compounds of formula (2), (2b), (2b-1), (2b-2), (2b-3), (2b-4), (2b-5) or (2b-6), M is particularly preferred to be phenyl, deuterated phenyl, 1,3-biphenyl, 1,4-biphenyl, terphenyl, partially deuterated terphenyl, tetraphenyl, naphthyl, fluorenyl, 9,9-diphenylfluorenyl, bisspirofluorenyl or biphenylenemethyl.

[0166] In compounds of formula (2b-1), (2b-2), (2b-3), (2b-4), (2b-5), or (2b-6), the labels c, d, e, and f are preferably 0 or 1.

[0167] Therefore, the present invention also provides an organic electroluminescent device as described above or as preferably described above, wherein at least one compound of formula (2) corresponds to a compound of formula (2b), (2b-1), (2b-2), (2b-3), (2b-4), (2b-5) or (2b-6) or a preferred embodiment of these compounds.

[0168] A preferred embodiment of the device according to the invention includes the use of a compound of formula (2) as the main material 2, wherein c and f are 0 or 1, d and e are 0, and x, x1, y, and y1 independently represent 0 or 1 in each case, but the sum of x and y is at least 1 and the sum of x1 and y1 is at least 1. Such a compound of formula (2) as described above is preferably represented by the following formula (2c).

[0169]

[0170] Where X and X 1 As defined in the context,

[0171] K and M are each independently associated with X or X. 1 Together they form heteroaromatic ring systems with 14 to 40 ring atoms.

[0172] x, x1, y and / or y1 are 0 or 1, and the sum of x and y is at least 1 and the sum of x1 and y1 is at least 1.

[0173] In the preferred compounds of formula (2c), the sum of x and y is 1 or 2 and the sum of x1 and y1 is 1. In the particularly preferred compounds of formula (2c), the sum of x and y is 1 and the sum of x1 and y1 is 1 in each case.

[0174] Therefore, in compounds of formula (2) or (2c), K and M preferably form a heteroaromatic ring system. In compounds of formula (2) or (2c), X and X 1 The preferred bond is a direct bond or C(CH3)2.

[0175] Preferred compounds of formula (2) or (2c) can be represented by formulas (2c-1) to (2c-8).

[0176]

[0177]

[0178] Preferred compounds of formula (2c) also include compounds H9, H11, H12, H13, H14, H15, H19 and H20 as described below.

[0179] Therefore, the present invention also provides an organic electroluminescent device as described above or as preferably described above, wherein at least one compound of formula (2) corresponds to a compound of formula (2c), (2c-1), (2c-2), (2c-3), (2c-4), (2c-5), (2c-6), (2c-7) or (2c-8).

[0180] In a preferred embodiment of the compound of formula (2), (2a), (2b), (2b-1), (2b-2), (2b-3), (2b-4), (2b-5), or (2b-6), the carbazole and the bridged carbazole are bonded to each other at the 3-position in each case.

[0181] In a preferred embodiment of the compound of formula (2c), the two bridged carbazoles are bonded to each other at position 3 in each case.

[0182] Examples of suitable host materials of formulas (2), (2a), (2b), (2b-1), (2b-2), (2b-3), (2b-4), (2b-5) and (2c) selected according to the present invention and preferably used in combination with at least one compound of formula (1) in the electroluminescent device of the present invention are the structures given in Table 2 below.

[0183] Table 2:

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190] In the electroluminescent device of the present invention, compounds of formula (2) that are particularly suitable for use in combination with at least one compound of formula (1) are compounds H1 to H27:

[0191]

[0192]

[0193]

[0194] The preparation of compounds of formula (2) or preferred compounds of formulas (2), (2a), (2b), (2b-1), (2b-2), (2b-3), (2b-4), (2b-5), and (2c), or the compounds in Table 2, and H1 to H27 are known to those skilled in the art. These compounds can be prepared by synthetic steps known to those skilled in the art, such as halogenation, preferably bromination, and subsequent organometallic coupling reactions, such as Suzuki coupling, Heck coupling, or Hartwig-Buchwald coupling. Some compounds of formula (2) are commercially available.

[0195] Formula (1) and its constituent materials as preferred embodiments or compounds E1 to E27 in Table 1 can be combined with formulas (2), (2a), (2b), (2), (2a), (2b), (2b-1), (2b-2), (2b-3), (2b-4), (2b-5), (2c), (2c-1), (2c-2), (2c-3), (2c-4), (2c-5), (2c-6), (2c-7) and (2c-8) and their constituent materials as preferred embodiments or compounds H1 to H27 in Table 2 as needed in the device of the present invention.

[0196] As described above, the aforementioned specific combination of the main material of formula (1) and the main material of formula (2) is preferred. Preferred combinations of main materials are also described below.

[0197] The present invention also provides mixtures comprising at least one compound of formula (1) and at least one compound of formula (2).

[0198]

[0199] The symbols and markings used are as follows:

[0200] Y is independently N or [L] in each case. n -Ar2 or [L]-R * Where exactly two Ys are N and are bound by at least one group [L]-R* or [L]. n Separated by -Ar2;

[0201] V is either O or S;

[0202] Rx is [L] n -Ar2 or [L]-R * ;

[0203] R * It is a triphenylidene group, which can be substituented by exactly one R group. #Substitution and / or substitution by one or more groups R;

[0204] The condition is that the substituent [L]-R * It appears exactly once in the compound of formula (1);

[0205] n is 0 or 1;

[0206] m is 0 or 1;

[0207] L is independently the same or different in each case and represents an aryl group, a divalent dibenzofuran group or a divalent dibenzothiophene group having 6 to 20 carbon atoms, each of which may be substituted by one or more groups R;

[0208] Ar2 may be the same or different in each case and represents an aromatic ring system having 6 to 30 ring atoms that can be substituted by one or more groups R;

[0209] R may be the same or different in each case and is selected from D, F, CN, a straight-chain alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, wherein one or more non-adjacent CH2 groups may be R 2 C = CR 2 The hydrogen atoms can be replaced by O or S, and one or more of the hydrogen atoms can be replaced by D, F or CN;

[0210] R# is an aryl group having 6 to 20 carbon atoms, said aryl group may be replaced by one or more groups R;

[0211] R 2 In each case, the same or different and selected from H, D, F, CN, straight-chain alkyl groups having 1 to 20 carbon atoms or branched or cyclic alkyl groups having 3 to 20 carbon atoms, wherein one or more non-adjacent CH2 groups may be replaced by O or S and wherein one or more hydrogen atoms may be replaced by D, F or CN.

[0212] K, M: When x and y are 0 and when x1 and y1 are 0, K and M are independently unsubstituted or partially or fully deuterated or R having 6 to 40 ring atoms. * - Monosubstituted aromatic ring systems, or

[0213] K, M: As long as the values ​​of x, x1, y and / or y1 are 1, then K and M are independently related to X or X 1 Together they form a heteroaromatic ring system with 14 to 40 ring atoms;

[0214] x and x1 are each 0 or 1 independently in each case;

[0215] y and y1 are each 0 or 1 independently in each case;

[0216] X and X 1 In each case, it is independently a bond or C(R) + )2;

[0217] R 0 In each case, it is independently an unsubstituted or partially or fully deuterated aromatic ring system having 6 to 18 ring atoms;

[0218] R + In each case, it is independently a straight-chain or branched alkyl group having 1 to 4 carbon atoms, and

[0219] c, d, e, and f are independently 0 or 1.

[0220] The foregoing matters concerning the main materials of formulas (1) and (2) and their preferred embodiments and combinations thereof also apply accordingly to the mixtures according to the invention.

[0221] A particularly preferred mixture of the 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 E27 with the compounds in Table 2.

[0222] The very particularly preferred mixture of the main material of formula (1) and the main material of formula (2) used in the device of the present invention is obtained by combining compounds E1 to E27 and compounds H1 to H27 as shown in Table 3 below.

[0223] Table 3:

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233] In the mixture of the present invention or in the light-emitting layer of the device of the present invention, based on the total mixture or based on the total composition of the light-emitting layer, the concentration of the electron transport host material of the preferred formula (1) as described above 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%.

[0234] In the mixture of the present invention or in the light-emitting layer of the device of the present invention, based on the total mixture or based on the total composition of the light-emitting layer, the concentration of the hole transport host material of formula (2) as described above or as preferably stated above 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%.

[0235] The present invention also relates to a mixture, which, in addition to the aforementioned main materials 1 and 2, particularly mixtures M1 to M729, as described above or as preferably described above, contains at least one phosphorescent material.

[0236] The present invention also relates to an organic electroluminescent device as described above or as preferably described above, wherein the light-emitting layer, in addition to the aforementioned main materials 1 and 2, especially material combinations M1 to M729, as described above or as preferably described above, also contains at least one phosphorescent material.

[0237] The term "phosphorescent luminescent material" generally refers to compounds that emit light from an excited state with high spin multiplicity, i.e., a spin state > 1, via a spin-forbidden transition, such as from a triplet state or a state with an even higher spin quantum number, such as a quintet state. This should preferably be understood as referring to a transition from a triplet state.

[0238] Suitable phosphorescent emitters (= triplet emitters) are, in particular, compounds that emit light when properly excited, preferably in the visible light region, and also 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 compounds of metals having such atomic numbers. 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.

[0239] Generally speaking, all phosphorescent complexes for phosphorescent OLEDs are suitable, based on existing technology and as known to those skilled in the art of organic electroluminescent devices.

[0240] According to the present invention, the preferred phosphorescent emitter conforms to formula (3).

[0241]

[0242] The symbols and notations in equation (3) are defined as follows:

[0243] When n+m is 3, n is 1 or 2, and m is 2 or 1.

[0244] X is N or CR.

[0245] R 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 7 carbon atoms and which may be partially or fully substituted with deuterium.

[0246] Therefore, the present invention also provides an organic electroluminescent device as described above or as preferably described above, characterized in that the light-emitting layer, in addition to the main materials 1 and 2, also contains at least one phosphorescent material conforming to formula (3) as described above.

[0247] In the light emitter of the formula (3), n is preferably 1 and m is preferably 2.

[0248] In the light emitter of the formula (3), preferably, one X is selected from N and the other X are CR.

[0249] In the light emitter of formula (3), at least one R is preferably different from H. In the light emitter of formula (3), preferably two Rs are different from H and have one of the other definitions given above for the light emitter of formula (3).

[0250] Preferred phosphorescent emitters according to the present invention conform to formulas (I), (II) and (III).

[0251]

[0252] The symbols and notations for these equations (I), (II), and (III) are defined as follows:

[0253] R1 is H or D, and R2 is H, D, or a branched or straight-chain alkyl group having 1 to 10 carbon atoms, or a partially or fully deuterated branched or straight-chain alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 4 to 10 carbon atoms and which may be partially or fully substituted with deuterium.

[0254] Preferred phosphorescent emitters according to the present invention conform to formulas (IV), (V) and (VI),

[0255]

[0256] The symbols and notations for these equations (IV), (V), and (VI) are defined as follows:

[0257] R1 is H or D, and R2 is H, D, F, or a branched or straight-chain alkyl group having 1 to 10 carbon atoms, or a partially or fully deuterated branched or straight-chain alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 4 to 10 carbon atoms and which may be partially or fully substituted with deuterium.

[0258] Table 4 below lists preferred examples of phosphorescent luminescent materials.

[0259] Table 4:

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272] In the mixtures of the present invention or in the light-emitting layer of the device of the present invention, any mixture selected from the summarized mixtures M1 to M729 is preferably combined with a compound of formula (3) or a compound of formulas (I) to (VI) or a compound in Table 4.

[0273] The light-emitting layer in the organic electroluminescent device of the present invention, which contains at least one phosphorescent light-emitting element, 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.

[0274] The yellow emitting layer is understood herein to be a layer with a maximum photoluminescence value in the range of 540 to 570 nm. The orange emitting layer is understood to be a layer with a maximum photoluminescence value in the range of 570 to 600 nm. The red emitting layer is understood to be a layer with a maximum photoluminescence value in the range of 600 to 750 nm. The green emitting layer is understood to be a layer with a maximum photoluminescence value in the range of 490 to 540 nm. The blue emitting layer is understood to be a layer with 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 layer thickness of 50 nm at room temperature, the layer having the present invention combination of the host material of formulas (1) and (2) with a suitable emitting body.

[0275] The photoluminescence spectrum of the layer is recorded, for example, using a commercial photoluminescence spectrometer.

[0276] 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 of moles. A suitable solvent is any solvent in which the selected luminescent material is dissolved at the mentioned concentration. Particularly suitable solvents are typically toluene or 2-methyl-THF, and also dichloromethane. Measurements are performed using a commercial photoluminescence spectrometer. The triplet energy T1, expressed in eV, is determined from the photoluminescence spectrum of the luminescent material. First, the maximum peak value Plmax (in nm) of the photoluminescence spectrum is determined. Then, the maximum peak value Plmax (in nm) is converted to eV using the following formula: E(T1, in eV) = 1240 / E(T1, in nm) = 1240 / Plmax (in nm).

[0277] Therefore, the preferred phosphorescent emitter is a yellow emitter, preferably the yellow emitter of formula (3), formulas (I) to (VI) or Table 4, with a triplet energy T1 preferably of about 2.3 eV to about 2.1 eV.

[0278] Therefore, the preferred phosphorescent emitter is a green emitter, preferably the green emitter of formula (3), formulas (I) to (VI) or the green emitter in Table 4, with a triplet energy T1 preferably of about 2.5 eV to about 2.3 eV.

[0279] Therefore, the particularly preferred phosphorescent emitter is a green emitter, preferably the green emitter of formula (3), formulas (I) to (VI) or Table 4 as described above, with a triplet energy T1 preferably of about 2.5 eV to about 2.3 eV.

[0280] Most preferably, a green light emitter as described above, preferably of formula (3), formulas (I) to (VI) or the green light emitter in Table 4, is selected for use in the composition of the present invention or the light-emitting layer of the present invention.

[0281] Fluorescent light emitters can also be present in the light-emitting layer of the device of the present invention.

[0282] Preferred fluorescent emitters are selected from aryl amines. In the context of this invention, aryl amines or aromatic amines are understood to refer to compounds containing three substituted or unsubstituted aromatic or heteroaromatic ring systems directly bonded to nitrogen.

[0283] In another preferred embodiment of the invention, the at least one light-emitting layer of the organic electroluminescent device may contain other host materials or matrix materials in addition to the host materials 1 and 2 as described above or as preferably described above, 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, as described above, there is one matrix component in addition to host materials 1 and 2). Particularly suitable matrix materials that can be used 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).

[0284] Wide bandgap material is understood herein to mean a material within the scope of the disclosure of US 7,294,849, characterized in that the bandgap is at least 3.5 eV, and the bandgap is understood to mean the bandgap between the HOMO and LUMO energies of a material.

[0285] Preferably, the mixed matrix system is optimized for the luminescent material of formula (3), formulas (I) to (VI) or Table 4.

[0286] 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 mixtures are material mixtures used directly to manufacture the light-emitting layer. These mixtures are also called premixed systems, which serve as the sole material source in the vapor deposition of the host material of the light-emitting layer and have a constant mixing ratio in the 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 precisely driving multiple material sources.

[0287] In another 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 contains the phosphorescent emitter as described above. As mentioned above, the mixture can also be used as the sole material source when the mixing ratio is appropriate in vapor deposition.

[0288] Therefore, the components or ingredients of the light-emitting layer of the device of the present invention can be processed by vapor deposition or from solution. For this purpose, a combination of materials 1 and 2 as described above or as preferably described above is provided in a formulation containing at least one solvent, optionally combined with a phosphorescent emitter as described above or as preferably described above. For example, these formulations can be solutions, dispersions, or emulsions. For this purpose, a mixture of two or more solvents may be preferred.

[0289] Therefore, the present invention also provides a formulation comprising a mixture of the main materials 1 and 2 as described above, the mixture optionally combined with a phosphorescent emitter as described above or as preferably described above, and at least one solvent.

[0290] Suitable and preferred solvents are, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, naphthalene, o-dimethoxybenzene, THF, methyl-THF, THP, chlorobenzene, dimethylbenzene, etc. 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, isopropylbenzene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decahydronaphthalene, dodecane Benzene, ethyl benzoate, indene, methyl benzoate, NMP, p-cymene, 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, hexamethylindene, or mixtures of these solvents.

[0291] The formulation may also contain at least one other organic or inorganic compound, particularly other luminescent compounds and / or other matrix materials, also used in the luminescent layer of the device of the present invention. Suitable luminescent compounds and other matrix materials have been detailed above.

[0292] According to the preferred embodiments and the luminescent compounds, the luminescent layer in the device of the present invention, based on the total composition of the luminescent material and the matrix material, preferably contains 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%, a matrix material containing at least one compound of formula (1) and at least one compound of formula (2) according to the preferred embodiments. Accordingly, based on the total composition of the luminescent layer containing the luminescent material and the matrix material, the luminescent layer in the device of the present invention preferably contains 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 solution, it is preferable to use the corresponding amount in weight % rather than the amount in volume % specified above.

[0293] According to the preferred embodiment and the luminescent compound, the luminescent layer in the device of the present invention preferably contains the matrix material of formula (1) and the matrix material of formula (2) in a volume 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 solution, it is preferable to use the corresponding ratio in weight % rather than the ratio in volume % specified above.

[0294] The present invention also relates to organic electroluminescent devices as described above or preferably as described above, wherein the organic layer comprises a hole injection layer (HIL) and / or a hole transport layer (HTL), wherein the hole injection material and the hole transport material are monoamines without carbazole units. The hole injection material and the hole transport material preferably comprise monoamines containing fluorene or bis-spirofluorene groups but without carbazole units.

[0295] The preferred monoamine used in the organic layer of the device according to the present invention can be described by formula (4).

[0296]

[0297] The symbols and notations for equation (4) are defined as follows:

[0298] Ar and Ar' are, in each case, independently an aromatic ring system with 6 to 40 ring atoms or a heteroaromatic ring system with 7 to 40 ring atoms, excluding the carbazole unit in the heteroaromatic ring system;

[0299] n is 0 or 1 independently in each case;

[0300] m is 0 or 1 independently in each case.

[0301] Preferably, at least one Ar' in formula (4) is a group of formula (4a) or (4b).

[0302]

[0303] In formulas (4a) and (4b), R may be the same or different in each case and is selected from H, D, F, CN, a straight-chain alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, wherein one or more non-adjacent CH2 groups may be R 2 C = CR 2 The R atoms are replaced by O or S and one or more of them may be replaced by D, F or CN, and two of them may form a cyclic or polycyclic ring and * indicates a connection with the rest of the formula (4).

[0304] Table 5 describes the preferred monoamines used in the organic layer of the device according to the present invention.

[0305] Table 5:

[0306]

[0307]

[0308]

[0309]

[0310]

[0311] Preferred hole transport materials also include materials that are combined with the compounds in Table 5 or that can be used as substitutes or compounds for the materials in Table 5 in hole transport, hole injection or electron blocking layers, such as indofluorene derivatives, hexaazatriphenylide derivatives, monobenzoindofluorene, dibenzoindofluorene, and dihydroacridine derivatives.

[0312] The preferred layer sequence in the organic electroluminescent device of the present invention is as follows:

[0313] Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / electron injection layer / cathode.

[0314] This layer sequence is the preferred sequence.

[0315] At the same time, it should be pointed out again that not all of the mentioned layers need to exist and / or other layers may also exist.

[0316] The organic electroluminescent device of the present invention may contain two or more light-emitting layers. At least one of the light-emitting layers is the light-emitting layer of the present invention, which, as described above, contains at least one compound of formula (1) as host material 1 and at least one compound of formula (2) as host material 2. Particularly preferably, in this case, these light-emitting layers collectively have multiple emission peaks between 380 nm and 750 nm, resulting in overall white light emission.

[0317] The material used for the electron transport layer can be any material that serves as an electron transport material 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.

[0318] 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, main group metals, or lanthanides (e.g., Ca, Ba, Mg, Al, In, Yb, Sm, etc.). Alloys comprising alkali metals or alkaline earth metals and silver are also suitable, for example, alloys comprising magnesium and silver. In the case of multilayer structures, in addition to the metals mentioned, other metals with relatively high work function, such as Ag or Al, can be used, typically in combinations of these metals such as Ca / Ag, Mg / Ag, or Ba / Ag. 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 useful materials for this purpose are fluorides of alkali metals or alkaline earth metals, and their corresponding oxides or carbonates (e.g., LiF, Li₂O, BaF₂, MgO, NaF, CsF, Cs₂CO₃, etc.). Lithium quinoline (LiQ) can also be used for this purpose. The layer thickness is preferably between 0.5 nm and 5 nm.

[0319] 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 are suitable for this purpose, such as Ag, Pt, or Au. Secondly, metal / metal oxide electrodes (e.g., Al / Ni / NiO) are also preferred. x Al / PtO xFor some applications, at least one of the electrodes must be transparent or partially transparent to enable irradiation of organic materials (organic solar cells) or emission (OLEDs, O-lasers). Preferred anode materials are conductive mixed metal oxides. Indium tin oxide (ITO) or indium zinc oxide (IZO) are particularly preferred. Furthermore, conductive doped organic materials, especially conductive doped polymers, are also 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.

[0320] Since the presence of water and / or air can severely shorten the lifespan of the devices of the present invention, the organic electroluminescent devices of the present invention are appropriately (according to the application) structured, provided with contact connections and finally sealed during the manufacturing process.

[0321] The manufacture of the device of the present invention is not limited herein. One or more organic layers, including a light-emitting layer, can be coated by a sublimation method. In this case, in a vacuum sublimation system, at less than 10 -5 millibars, preferably less than 10 -6 The material is applied via vapor deposition at an initial pressure of millibars. However, in this case, the initial pressure can be even lower, for example, less than 10. -7 millibar.

[0322] The organic electroluminescent device of the present invention is preferably characterized by coating one or more layers by OVPD (organic vapor deposition) or by means of carrier gas sublimation. In this case, at 10 -5 The material is applied at a pressure between millibar and 1 bar. A special case of this method is OVJP (Organic Vapor Jetting), 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).

[0323] A further preferred feature of the organic electroluminescent device of the present invention is that one or more organic layers are generated 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, wherein the one or more organic layers comprise the composition of the present invention. For this purpose, soluble host materials 1 and 2 and a phosphorescent emitter are required. The advantage of processing from solution is 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.

[0324] Alternatively, a hybrid approach is feasible, for example, in which one or more layers are applied from a solution while one or more other layers are applied via vapor deposition.

[0325] These methods are generally known to those skilled in the art and can be applied to organic electroluminescent devices.

[0326] Therefore, the present invention also provides a method for manufacturing an organic electroluminescent device as described above or as preferably described above, characterized in that an organic layer, preferably a light-emitting layer, a hole injection layer and / or a hole transport layer, is applied by vapor deposition, especially by sublimation and / or by OVPD (organic vapor deposition) and / or by means of a carrier gas sublimation, or from a solution, especially by spin coating or by printing.

[0327] In the case of fabrication via vapor deposition, there are, in principle, two ways to apply or vapor deposit the organic layer, preferably the luminescent layer, of the present invention onto any substrate or prior layer. First, the materials used can each be initially loaded into a material source and ultimately evaporated from different material sources (“co-evaporation”). Second, the various materials can be premixed (premixed system), the mixture being initially loaded into a single material source and ultimately evaporated from therefrom (“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 precisely driving multiple material sources.

[0328] 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 above and at least one compound of formula (2) as described above or preferred above are deposited from at least two material sources successively or simultaneously from the gas phase, optionally deposited together with at least one phosphorescent material as described above or preferred above, and forming a light-emitting layer.

[0329] 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.

[0330] Therefore, the present invention also provides a method for manufacturing the device of the present invention, characterized in that the at least one compound of formula (1) and the at least one compound of formula (2) are mixed and deposited from the gas phase successively or simultaneously with the at least one phosphorescent emitter to form an emitting layer.

[0331] The present invention also provides a method for manufacturing the device of the present invention as described above or as preferably described above, characterized in that the compound of at least one formula (1) and the compound of at least one formula (2) described above or as preferably described above are applied from a solution together with the at least one phosphorescent emitter to form an emitting layer.

[0332] Compared with the prior art, the device of the present invention is characterized by the following surprising advantages:

[0333] Using the material combination of the main materials 1 and 2 as described above results in an increase in device lifespan.

[0334] As can be clearly seen in the embodiments given below, by comparing the data of the combined OLEDs with those of the prior art, it can be determined that the matrix material combination of the present invention in the EML results in a significant increase in device lifetime regardless of the emitter concentration.

[0335] It should be noted that the scope of this invention covers variations of the embodiments described herein. Any feature disclosed herein, unless expressly excluded, may be interchanged with a substitute feature for the same, equivalent, or similar purpose. Therefore, unless otherwise stated, any feature disclosed herein should be considered an example of a general series or an equivalent or similar feature.

[0336] Unless specific features and / or steps are mutually exclusive, all features of the invention can be combined with each other in any way. This is particularly true for preferred features of the invention. Similarly, features in non-essential combinations can be used separately (rather than in combination).

[0337] The technical teachings disclosed in this invention can be refined and combined with other examples.

[0338] The invention has been illustrated in more detail by way of the following embodiments, but is not intended to limit the invention.

[0339] Example

[0340] General method:

[0341] The Gaussian16 (Rev.B.01) software package was used in all quantum chemical calculations. The neutral singlet ground state was optimized at the B3LYP / 6-31G(D) level. The HOMO and LUMO values ​​of the ground state energy used for B3LYP / 6-31G(D) optimization were determined at the B3LYP / 6-31G(D) level. Then, singlet and triplet excitations (vertical excitations) of the TD-DFT were calculated using the same method (B3LYP / 6-31G(D)) and with the optimized ground state geometry. Standard settings for SCF and gradient convergence were used.

[0342] The HOMO, obtained through the energy calculations, represents the last orbital occupied by two electrons (alphaocc.eigenvalues), and the LUMO, representing the first unoccupied orbital (alpha virt.eigenvalues), are expressed in Hartree units, where Heh and Leh represent the HOMO and LUMO energies in Hartree units, respectively. These are used to determine the HOMO and LUMO values ​​in electron volts, calibrated using cyclic voltammetry as follows:

[0343] HOMOcorr=0.90603*HOMO-0.84836,

[0344] LUMOcorr=0.99687*LUMO-0.72445.

[0345] The triplet energy level T1 of a material is defined as the relative excitation energy (in eV) of the triplet state with the lowest energy, which is obtained through quantum chemical energy calculations.

[0346] 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, which is obtained through quantum chemical energy calculations.

[0347] The singlet state with the lowest energy is called S0.

[0348] The methods described herein are independent of the software package used and always yield the same results. Examples of programs frequently used for this purpose are "Gaussian09" (Gaussian, Inc.) and Q-Chem 4.1 (Q-Chem, Inc.). In this application, the software package "Gaussian16 (Rev.B.01)" is used to calculate the energy.

[0349] Example 1: OLED Manufacturing

[0350] Pre-treatment for OLED manufacturing: A glass plate coated with a 50nm thick structured ITO (indium tin oxide) is first treated with oxygen plasma, then with argon plasma, before coating. These plasma-treated glass plates form the substrate for applying the OLED.

[0351] 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 cathode. The cathode is formed of a 100 nm thick aluminum layer.

[0352] All materials are applied in a vacuum chamber via thermal vapor deposition. In this case, the luminescent layer always consists of at least one matrix material (host material), or for the purposes of this invention at least two matrix materials, and a luminescent dopant (emitting agent), which is added to (one or more) matrix materials in a specific volume ratio via co-evaporation. Similarly, the electron transport layer may also consist of a mixture of two materials.

[0353] The OLED was characterized in a standard manner. For this purpose, the electroluminescence spectrum and current-voltage-luminance characteristics (IUL characteristics) were measured. The EQE and current efficiency SE (in cd / A) were then calculated. SE was calculated under Lambertian emission characteristics.

[0354] Lifetime LT is defined as the time taken to reach a distance of mA / cm². 2 During the operation of the constant current density j0, the brightness changes from the initial brightness L0 (in cd / m²). 2 (Calculated) decreases to a specific ratio L1 (in cd / m 2 The figure L1 / L0 = 80% in Table 7 refers to the lifetime reported in the LT column, corresponding to the time (in hours) until the brightness drops to 80% of its initial value (L0).

[0355] Use of the mixture of the present invention in OLEDs

[0356] The following embodiments V1 to V16 and B1 to B37 (see Tables 6 and 7) illustrate the use of the material combinations of the present invention in OLEDs compared with material combinations in the prior art.

[0357] The structure of an OLED is shown in Table 6. Materials required for manufacturing an OLED, if not disclosed elsewhere, are shown in Table 8. Table 7 lists the device data for OLEDs.

[0358] The details reported in the form of VG1:H2:TEG1 (33%:60%:7%) 30nm show that, in a 30nm thick layer, comparative material 1 exists as host material 1 with a volume ratio of 33%, compound H2 exists as host material 2 with a ratio of 60%, and TEG1 exists with a ratio of 7%.

[0359] Examples V1 to V16 are comparative examples having an electronic transmission body according to the prior art or having a body H0 in V14. Examples B1 to B37 use the material combination of the present invention in EML.

[0360] By comparing the embodiments of the present invention with corresponding comparative examples, it becomes clear that the embodiments of the present invention each exhibit significant advantages in terms of device lifetime.

[0361] Table 6:

[0362]

[0363]

[0364]

[0365]

[0366]

[0367] Table 7: OLED Data

[0368]

[0369]

[0370] Table 8: Structural formulas of OLED materials used that have not been previously described:

[0371]

[0372]

[0373]

[0374]

[0375] Example 2: Synthesis of the host material and its precursors:

[0376] Unless otherwise stated, the following synthesis was carried out in a dry solvent under a protective gas atmosphere. The compounds of the present invention can be prepared by synthetic methods known to those skilled in the art.

[0377] a) 2,4-Diphenylbenzo[4,5]furano[3,2-d]pyrimidine

[0378]

[0379] 13 g (110.0 mmol) of phenylboronic acid, 13 g (55 mmol) of 2,4-dichlorobenzo[4,5]furano[3,2-d]pyrimidine, and 21 g (210.0 mmol) of sodium carbonate were suspended in 500 mL of ethylene glycol diamine ether and 500 mL of water. 913 mg (3.0 mmol) of tri-o-tolylphosphine and 112 mg (0.5 mmol) of palladium(II) acetate were added to the suspension, and the reaction mixture was refluxed and heated for 16 hours. After cooling, the organic phase was removed, the mixture was filtered through silica gel, and then concentrated to dryness. The residue was recrystallized from toluene and from dichloromethane / heptane. Yield: 15 g (47 mmol), 87% of theoretical value.

[0380] The following compounds were prepared in a similar manner:

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389] b) 8-Bromo-2,4-diphenylbenzo[4,5]furano[3,2-d]pyrimidine

[0390]

[0391] 61 g (190.0 mmol) of 2,4-diphenylbenzo[4,5]furano[3,2-d]pyrimidine was suspended in 2000 mL of acetic acid (100%) and 2000 mL of sulfuric acid (95-98%). 34 g (190 mmol) of NBS was added to the suspension in portions, and the mixture was stirred in the dark for 2 hours. Water / ice was then added, the solid was separated, and washed with ethanol. The residue was recrystallized in toluene. The yield was 65 g (163 mmol), equivalent to 86% of the theoretical yield.

[0392] The following compounds were prepared in a similar manner:

[0393]

[0394] c) 2,4-Diphenyl-8-(3-triphenylide-2-ylphenyl)benzofurano[3,2-d]pyrimidine

[0395]

[0396] 62.5 g (156 mmol) of 8-bromo-2,4-diphenyl-benzo[4,5]furano[3,2-d]pyrimidine, 59 g (170 mmol) of (3-triphenylide-2-ylphenyl)boronic acid, and 36 g (340 mmol) of sodium carbonate were suspended in 1000 mL of ethylene glycol diamine ether and 280 mL of water. 1.8 g (1.5 mmol) of tetrakis(triphenylphosphine)palladium(O) was added to the suspension, and the reaction mixture was refluxed and heated for 16 hours. After cooling, the organic phase was separated, filtered through silica gel, and concentrated to dryness. The product was purified by silica gel column chromatography with toluene / n-heptane (1:2) and finally sublimated under high vacuum. (p = 5 × 10⁻⁶) -7 (99.9% purity, millibars). Yield: 69 g (111 mmol), equivalent to 72% of the theoretical value.

[0397] The following compounds were prepared in a similar manner:

[0398]

[0399]

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

[0410]

[0411]

[0412]

[0413]

[0414]

[0415]

[0416]

[0417] d)(3-amino-6-bromo-benzofuran-2-yl)phenyl ketone

[0418]

[0419] 100 g (505 mmol) of 4-bromo-2-hydroxybenzonitrile and 100 g (505 mmol) of 2-bromo-1-phenylethyl ketone were initially charged together with 1500 ml of acetone. 1000 g of potassium carbonate was added in portions to the solution, followed by heating to 70 °C and stirring at this temperature for 2 hours. After cooling, the precipitated solid was filtered under vacuum, then stirred with water, filtered under vacuum again, and subsequently washed with methanol. The yield was 160 g (443 mmol), equivalent to 87% of the theoretical yield.

[0420] The following compounds were prepared in a similar manner:

[0421]

[0422]

[0423] e) 7-Bromo-2,4-diphenylbenzofurano[3,2-d]pyrimidine

[0424]

[0425] Under argon atmosphere, 167 g (0.53 mol) of (3-amino-6-bromo-benzofuran-2-yl)phenyl ketone and 218 g (2.1 mol) of benzonitrile were initially charged with 2000 mL of o-xylene. 87.5 g (0.79 mol) of sodium tert-amyloxide was added to the solution, followed by heating to 160 °C for two days. After cooling, the precipitated solid was filtered under vacuum, then stirred with hot water, filtered under vacuum again, and subsequently washed with n-heptane. The yield was 160 g (443 mmol), equivalent to 87% of the theoretical yield.

[0426] The following compounds were prepared in a similar manner:

[0427]

[0428]

Claims

1. An organic light-emitting electrochemical cell or organic light-emitting diode, said organic light-emitting electrochemical cell or organic light-emitting diode comprising an anode, a cathode and at least one organic layer containing at least one light-emitting layer, wherein said at least one light-emitting layer contains at least one compound of formula (1aa), (1ab), (1ac), (1ba), (1bb) or (1bc) as a host material 1 and at least one compound of formula (2a) or (2b) as a host material 2. The symbols and markings used are as follows: V is either O or S; R * It is a triphenylidene group, which can be substituented by exactly one R group. # Substitution and / or substitution by one or more groups R; n is 0 or 1; m is 0 or 1; L is independently the same or different in each case and is selected from L-1 to L-7 and L-14 to L-23, each of which can be substituted by one or more groups R. Where W is O or S; Ar2 may be the same or different in each case and represents an aromatic ring system having 6 to 30 ring atoms that can be substituted by one or more groups R; R is D; R# is a phenyl group that can be replaced by one or more groups R; M: Independently unsubstituted or partially or fully deuterated or R having 6 to 40 ring atoms * - Monosubstituted aromatic ring systems; K: When x and y are 0, K is independently an unsubstituted or partially or fully deuterated or R with 6 to 40 ring atoms. * - Monosubstituted aromatic ring systems, or K: As long as the value of x or y is 1, K independently forms a heteroaromatic ring system with 14 to 40 ring atoms together with X; x is 0 or 1 independently in each case; y is 0 or 1 independently in each case; X is a key independently in each case; R 0 In each case, independently, it is an unsubstituted or partially or fully deuterated aromatic ring system having 6 to 18 ring atoms; and c, d, e, and f are independently 0 or 1.

2. The organic light-emitting electrochemical cell or organic light-emitting diode according to claim 1, characterized in that... The main material 2 conforms to one of formulas (2b-1) or (2b-2). The symbols and markings used are the same as those defined in claim 1.

3. The organic light-emitting electrochemical cell or organic light-emitting diode according to claim 1 or 2, wherein V is O.

4. The organic light-emitting electrochemical cell or organic light-emitting diode according to claim 1 or 2, wherein L is selected from L-2, L-3, L-7, L-8, L-15, L-16, L-20 and L-22.

5. The organic light-emitting electrochemical cell or organic light-emitting diode according to claim 1 or 2, wherein the host material 1 is selected from the following compounds:

6. The organic light-emitting electrochemical cell or organic light-emitting diode according to claim 1 or 2, wherein the host material 2 is selected from the following compounds:

7. The organic light-emitting electrochemical cell or organic light-emitting diode according to claim 1 or 2, characterized in that... In addition to the light-emitting layer, the organic layer also includes a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, and / or a hole blocking layer.

8. The organic light-emitting electrochemical cell or organic light-emitting diode 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.

9. The organic light-emitting electrochemical cell or organic light-emitting diode according to claim 1 or 2, characterized in that... The organic layer comprises a hole injection layer and / or a hole transport layer, wherein the hole injection material and the hole transport material of the hole injection layer and / or the hole transport layer are monoamines that do not contain carbazole units.

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

11. The method according to claim 10, characterized in that... To fabricate the light-emitting layer, at least one compound of formula (1aa), (1ab), (1ac), (1ba), (1bb), or (1bc) and at least one compound of formula (2a) or (2b) are deposited sequentially or simultaneously from at least two material sources in the gas phase, optionally together with the at least one phosphorescent material.

12. The method according to claim 10, characterized in that... In order to manufacture the light-emitting layer, at least one compound of formula (1aa), (1ab), (1ac), (1ba), (1bb) or (1bc) and at least one compound of formula (2a) or (2b) are deposited in the gas phase as a mixture with the at least one phosphorescent material, either sequentially or simultaneously.

13. The method according to claim 10, characterized in that... To manufacture the light-emitting layer, at least one compound of formula (1aa), (1ab), (1ac), (1ba), (1bb), or (1bc) and at least one compound of formula (2a) or (2b) are applied from solution together with at least one phosphorescent material.

14. A mixture comprising at least one compound of formula (1aa), (1ab), (1ac), (1ba), (1bb), or (1bc) and at least one compound of formula (2a) or (2b), The symbols and markings used are as follows: V is either O or S; R * It is a triphenylidene group, which can be substituented by exactly one R group. # Substitution and / or substitution by one or more groups R; n is 0 or 1; m is 0 or 1; L is independently the same or different in each case and is selected from L-1 to L-7 and L-14 to L-23, each of which can be substituted by one or more groups R. Where W is O or S; Ar2 may be the same or different in each case and represents an aromatic ring system having 6 to 30 ring atoms that can be substituted by one or more groups R; R is D; R# is a phenyl group that can be replaced by one or more groups R; M: Independently unsubstituted or partially or fully deuterated or R having 6 to 40 ring atoms * - Monosubstituted aromatic ring systems; K: When x and y are 0, K is independently an unsubstituted or partially or fully deuterated or R with 6 to 40 ring atoms. * - Monosubstituted aromatic ring systems, or K: As long as the value of x or y is 1, K independently forms a heteroaromatic ring system with 14 to 40 ring atoms together with X; x is 0 or 1 independently in each case; y is 0 or 1 independently in each case; X is a key independently in each case; R 0 In each case, independently, it is an unsubstituted or partially or fully deuterated aromatic ring system having 6 to 18 ring atoms; and c, d, e, and f are independently 0 or 1.

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