Materials for electronic devices

Abstract

The present application relates to compounds represented by formula (1), to methods of preparing such compounds, to electronic devices comprising one or more such compounds, and to the use of such compounds in electronic devices.

Description

Technical Field

[0001] The present invention relates to compounds represented by formula (1), methods for preparing such compounds, electronic devices containing one or more such compounds, and the use of such compounds in electronic devices. Background Technology

[0002] In the context of this application, electronic devices are understood to mean so-called organic electronic devices that contain organic semiconductor materials as functional materials. More specifically, they are understood to mean OLEDs (Organic Light Emitting Diodes). The term OLED is understood to mean an electronic device having one or more layers containing organic compounds and emitting light when a voltage is applied. The general principles of the structure and function of OLEDs are known to those skilled in the art.

[0003] There is great interest in improving performance data in electronic devices, particularly OLEDs. However, no completely satisfactory solution has yet been found in these areas.

[0004] The light-emitting layer and the hole-transporting layer have a significant impact on the performance data of electronic devices. Novel compounds for these layers are being sought, particularly hole-transporting compounds and compounds that can serve as hole-transporting matrix materials in the light-emitting layer, especially as hole-transporting matrix materials for phosphorescent emitters. To this end, compounds with high glass transition temperatures, high stability, and high hole conductivity are being specifically sought. High stability of the compounds is a prerequisite for achieving long lifespans in electronic devices. Furthermore, there is a need to find compounds that can be used in electronic devices to improve device performance data, particularly in terms of high efficiency, long lifespan, and low operating voltage.

[0005] In the prior art, spiroalkyl derivatives are known to be used as hole-transporting materials and hole-transporting matrix materials in electronic devices. However, there is still room for improvement in the aforementioned properties.

[0006] WO 20080872 A describes spiroalkyl derivatives with adamantyl closed rings as dopant materials.

[0007] WO 21135207 A, WO 21213109 A, CN 113620917 A and WO 20248755 A describe spiroalkyl derivatives with adamantyl cyclic closure as hole transport materials.

[0008] WO 22183798 A describes spiroalkyl derivatives linked to bicyclic (3.3.1) nonyl groups substituted at positions 3 and 7 as hole-modifying layer materials.

[0009] It has been found that spiroalkyl derivatives of the following formula, characterized by specific structures, are highly suitable for use in electronic devices. They are particularly suitable for use in OLEDs, and even more particularly as hole transport materials and as hole transport matrix materials, especially as hole transport matrix materials for phosphorescent emitters. These compounds result in devices with high lifetime, high efficiency, and low operating voltage. Further preferably, the discovered compounds possess high glass transition temperatures, high stability, low sublimation temperatures, good solubility, good synthetic accessibility, and high hole conductivity. Summary of the Invention

[0010] Therefore, the present invention first provides a compound represented by formula (1):

[0011]

[0012] Equation (1)

[0013] Equation (2)

[0014] The groups and markings that appear are as follows: X is the same or different in each case, and is N or CR. 1 One of X is CR 1 And R 1 It is a group represented by formula (2); It is the binding site between the group represented by formula (2) and formula (1); L 11 To L 13 Each occurrence may represent a single bond or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which can be represented by one or more R atoms. 3 Group substitution; i11 to i13 represent 1, 2 or 3 in each occurrence, either the same or different. R 1 Each occurrence may represent H, D, F, Cl, Br, I, CHO, CN, N(R) in the same or different ways. 4 )2,C(=O)R 4 , P(=O)(R 4 )2,S(=O)R 4 S(=O)2R 4 NO2, Si(R) 4 )3, B(OR 4 )2, OSO2R 4The groups are straight-chain alkyl, alkoxy, or thioalkyl groups having 1 to 40 carbon atoms, or branched or cyclic alkyl, alkoxy, or thioalkyl groups having 3 to 40 carbon atoms, each of which may be further classified by one or more groups R. 4 Substitution, wherein in each case one or more non-adjacent CH2 groups may be replaced by R 4 C=CR 4 C≡C, Si(R) 4 )2、Ge(R 4 )2、Sn(R 4 )2. C=O, C=S, C=Se, P(=O)(R 4 ), SO, SO2, O, S or CONR 4 The aromatic or heteroaromatic ring system having 5 to 60 ring atoms, wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN, or NO2, and in each case the aromatic or heteroaromatic ring system may be replaced by one or more R groups. 4 Substitution, or an aryloxy group having 5 to 60 ring atoms, said aryloxy group may be replaced by one or more R groups. 4 Substitution, wherein the group R 1 The two components can form aliphatic or aromatic ring systems that are monocyclic or polycyclic, and these systems can be converted by one or more groups R. 4 replace; R 2 Each occurrence may represent H, D, F, Cl, Br, I, CHO, CN, N(R) in the same or different ways. 5 )2,C(=O)R 5 , P(=O)(R 5 )2,S(=O)R 5 S(=O)2R 5 NO2, Si(R) 5 )3, B(OR 5 )2, OSO2R 5 The groups are straight-chain alkyl, alkoxy, or thioalkyl groups having 1 to 40 carbon atoms, or branched or cyclic alkyl, alkoxy, or thioalkyl groups having 3 to 40 carbon atoms, each of which may be further classified by one or more groups R. 5 Substitution, wherein in each case one or more non-adjacent CH2 groups may be replaced by R 5 C=CR 5 C≡C, Si(R) 5 )2、Ge(R 5 )2、Sn(R 5 )2. C=O, C=S, C=Se, P(=O)(R 5 ), SO, SO2, O, S or CONR5 The aromatic or heteroaromatic ring system having 5 to 60 ring atoms, wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN, or NO2, and in each case the aromatic or heteroaromatic ring system may be replaced by one or more R groups. 5 Substitution, or an aryloxy group having 5 to 60 ring atoms, said aryloxy group may be replaced by one or more R groups. 5 Substitution, wherein the group R 2 and R 5 The two aliphatic or aromatic ring systems that do not form monocyclic or polycyclic rings; n2 represents an integer selected from 1 to 14, either the same or different each time it appears; Ar 11 and Ar 12 Each occurrence may refer to an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, and in each case may also be represented by one or more R groups. 6 Substitution, in which two adjacent substituents Ar 11 and Ar 12 It can form monocyclic or polycyclic aliphatic or aromatic ring systems, which can be formed by one or more groups R. 6 replace, R 3 To R 6 Each occurrence may represent H, D, F, Cl, Br, I, CHO, CN, N(Ar)2, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R')3, B(OR')2, OSO2R ´ 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, each of which may be substituted by one or more groups R', wherein in each case one or more non-adjacent CH2 groups may be substituted by R'C=CR', C≡C, Si(R')2, Ge(R')2, Sn(R')2, C=O, C=S, C=Se, P(=O)(R'), SO, SO2, O, S, or CONR', and wherein one or more H atoms may be substituted by D, F, Cl, Br, I, CN, or NO2; an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, wherein in each case the aromatic or heteroaromatic ring system may be substituted by one or more groups R', or an aryloxy group having 5 to 60 ring atoms, wherein the aryloxy group may be substituted by one or more groups R', wherein group R 3 R 4 and R 6The two aliphatic or aromatic ring systems in the ring can form monocyclic or polycyclic aliphatic or aromatic ring systems, wherein the aliphatic or aromatic ring system can be substituted by one or more groups R'; Ar, in each instance, may refer to an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which may in each case be substituted by one or more groups R'. R´, in each occurrence, may represent H, D, F, Cl, Br, I, 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, wherein in each case one or more non-adjacent CH2 groups may be replaced by SO, SO2, O, or S, and one or more H atoms may be replaced by D, F, Cl, Br, or I, or an aromatic or heteroaromatic ring system having 5 to 24 ring atoms.

[0015] The present invention also provides a method for preparing compounds represented by formula (1) as described above or preferably described below.

[0016] The present invention also provides a formulation comprising at least one compound represented by formula (1) as described above or preferably described below and at least one solvent.

[0017] The present invention also provides an electronic device comprising at least one compound represented by formula (1) as described above or preferably described below.

[0018] The present invention also provides the use of compounds represented by formula (1) as described above or preferably below in electronic devices. Detailed Implementation

[0019] In the context of this invention, "D" or "D atom" refers to deuterium.

[0020] The following definitions apply to the chemical groups used as general definitions. They apply unless a more specific definition is given.

[0021] In the context of this invention, an aryl group contains 6 to 60 ring atoms, preferably carbon atoms. In the context of this invention, a heteroaryl group contains 5 to 60 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 or heteroaryl is understood herein to mean a simple aromatic ring, i.e., a phenyl ring derived from benzene, or a simple heteroaryl ring, such as that derived from pyridine, pyrimidine, or thiophene, or a fused aryl or heteroaryl, such as that derived from naphthalene, anthracene, phenanthrene, quinoline, or isoquinoline. Therefore, an aryl group having 6 to 18 carbon atoms is preferably phenyl, naphthyl, phenanthrene, or biphenylidene, and there is no limitation on the connection of the aryl group as a substituent. In the context of this invention, the aryl or heteroaryl group may contain one or more R groups, wherein the substituent R is described below.

[0022] In the context of this invention, an aromatic ring system contains 6 to 60 ring atoms. The aromatic ring system also includes aryl groups as described above.

[0023] The aromatic ring system having 6 to 18 carbon atoms is preferably selected from phenyl, fully deuterated phenyl, biphenyl, naphthyl, phenanthryl and biterphenylidene.

[0024] In the context of this invention, a heteroaromatic ring system contains 5 to 60 ring atoms and at least one heteroatom. A preferred heteroaromatic ring system has 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.

[0025] In the context of this invention, aromatic or heteroaromatic ring systems are understood to mean not necessarily containing only aryl or heteroaromatic groups, but rather systems in which multiple aryl or heteroaromatic groups can also be interrupted by non-aromatic units (preferably less than 10% of atoms other than H), such as carbon, nitrogen, or oxygen atoms, or carbonyl groups. For example, in the context of this invention, systems such as 9,9'-spirodifluorene, 9,9-diarylfluorene, triarylamines, diaryl ethers, stilbene, etc., should therefore also be considered aromatic or heteroaromatic ring systems, as should systems in which two or more aryl groups are interrupted by, for example, straight-chain or cyclic alkyl or 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.

[0026] Aromatic or heteroaromatic ring systems having 5 to 60 ring atoms and being able to be attached to aromatic or heteroaromatic systems at any desired position are understood to refer to groups derived, for example, from the following substances: benzene, naphthalene, anthracene, benzo[a]anthracene, phenanthrene, benzo[a]phenanthrene, pyrene, leucine, perylene, fluoranthene, benzo[a]fluoranthene, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, diphenylenexide, terphenyl, diphenylenexide, fluorene, spirodifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indo[a]fluorene, cis or trans monobenzo[a]indo[a]fluorene, cis or trans dibenzo[a]indo[a]fluorene, trimer indo[a]fluorene, iso[a]fluorene, etc. Trimeric indene, spirotrimeric indene, spiroisotrimeric 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, phenothiazine, pyrazole, indazole, imidazole, benzimidazole, naphthiamidazole, phenanthrenemidazole, pyridinium-imidazolium, quinoxaline-imidazolium, β-azole, benzo[β-azole], naphtho[β-azole], anthraxo[β-azole], phenanthrene[β-azole], iso[β-azole], 1,2-thiazole, 1,3-thiazole, benzo[β-thiazole], pyridazine, benzo[β-pyridazine], pyrimidine, benzo[β-pyrimidine], 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, phenothiazine, fluorescein ring, naphthidine, azacarbazole, benzo[β-carbline], phenanthrene, 1,2,3- Triazole, 1,2,4-triazole, benzotriazole, 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, indene, and benzothiadiazole.

[0027] In each case, the abbreviation Ar independently refers to an aromatic or heteroaromatic ring system having 5 to 40 ring atoms and being substituted with one or more R′ groups, or a heteroaromatic ring system having 5 to 24 ring atoms and being substituted with one or more R′ groups, wherein details of the aromatic or heteroaromatic ring system apply accordingly. The one or more R′ groups have the definitions described above or below. In each case, the abbreviation Ar preferably independently refers to an aryl group having 6 to 40 ring atoms and being substituted with one or more R′ groups, or a heteroaromatic group having 5 to 40 ring atoms and containing O or S as heteroatoms, which may be substituted with one or more R′ groups, wherein details of the aryl or heteroaromatic group and R′ as described above or below apply accordingly.

[0028] abbreviation Ar 11 and Ar 12 The same or different in each case, and having 5 to 60 ring atoms and being able to be one or more R 6 Aromatic or heteroaromatic ring systems with substituent groups, wherein R 6 Group or substituent R 6 It has the definition described above or below. Preferably, Ar 11 and Ar 12 In each case, they may be the same or different, and are aryl groups with 6 to 40 ring atoms as described above.

[0029] In the context of this invention, cyclic alkyl, alkoxy, or thioalkyl are understood to mean monocyclic, bicyclic, or polycyclic groups.

[0030] In the context of this invention, straight-chain alkyl groups having 1 to 40 carbon atoms, and branched or cyclic alkyl groups having 3 to 40 carbon atoms are understood to mean, 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, cycloheptyl, 1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl, 1-bicyclo[2.2.2]octyl, 2-bicyclo[2.2.2]octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, 1,1-dimethyl-n-hex-1-yl, 1,1-Dimethyl-n-hept-1-yl, 1,1,dimethyl-n-oct-1-yl, 1,1,-dimethyl-n-dec-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-hexane-1-yl, 1,1-diethyl-n-heptane-1-yl, 1,1-diethyl-n-octane-1-yl - 1,1-diethyl-n-decyl-1-yl, 1,1-diethyl-n-dodecyl-1-yl, 1,1-diethyl-n-tetradecyl-1-yl, 1,1-diethyl-n-hexadecyl-1-yl, 1,1-diethyl-n-octadecyl-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.

[0031] Straight-chain alkoxy groups having 1 to 40 carbon atoms or branched-chain alkoxy groups having 3 to 40 carbon atoms are understood to mean, for example, methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, or 2-methylbutoxy.

[0032] Straight-chain thioalkyl groups having 1 to 40 carbon atoms are understood to mean, for example, S-alkyl groups such as thiomethyl, 1-thioethyl, 1-thioisopropyl, 1-thion-propyl, 1-thioisobutyl, 1-thio-n-butyl, or 1-thio-tert-butyl.

[0033] An aryloxy or heteroaryloxy group having 5 to 60 ring atoms means an O-aryl or O-heteroaryl group, and means that the aryl or heteroaryl group is bonded by an oxygen atom, wherein the aryl or heteroaryl group is defined as described above.

[0034] Aryl or heteroaryl having 5 to 40 ring atoms means that the alkyl group as described above is replaced by an aryl or heteroaryl group, wherein the aryl or heteroaryl group is defined as described above.

[0035] In the context of this specification, the phrase "two or more groups can form a ring together" should be understood to specifically mean that the two groups are connected to each other by chemical bonds. This is illustrated by the following scheme:

[0036] However, in addition, the above wording should also be understood to mean that if one of the two groups is hydrogen, then the second group binds to the position where the hydrogen atom is bonded, thereby forming a ring. This will be illustrated by the following scheme:

[0037] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), at least one of formulas 1-1 to 1-4, and at least one of formulas 1-1, 1-2 and 1-4 are preferred, and the compound represented by formula 1-2 is more preferred:

[0038]

[0039]

[0040] In equations 1-1 to 1-4, X, L 11 To L 13 i11 to i13, R 2 n2, Ar 11 and Ar 12 It has the definition given above or below.

[0041] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), X may be the same or different in each case, and is N or CR. 1 One of X is CR 1 And R 1 It is a group represented by formula (2).

[0042] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), X may be the same or different in each case, and is CR 1 .

[0043] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), the group represented by formula (2) is represented by formula 2-1 or 2-2, wherein the group represented by formula 2-1 is preferred: , In equations 2-1 and 2-2, L 2 It is a single bond, N(R) 61 ), S, O, C(R) 61 (R) 62 ), C(R 61 )=C(R 62 ) or Si(R 61 (R) 62 ); i2 is 0 or 1; R 61 and R 62 "Each is independent" refers to the definition given above or below; L 11 To L 13 i11 to i13, R 6 Ar 11 and Ar 12 It has the definition given above or below.

[0044] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), L 11 To L 13 Each occurrence may represent a single bond or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be represented by one or more R atoms. 3Group substitution.

[0045] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), L 11 To L 13 Each occurrence is identical or different from single bonds and divalent groups derived from the following substances: benzene, biphenyl, terphenyl, tetraphenyl, naphthalene, phenanthrene, fluorene, especially 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzo[a]fluorene, spirodifluorene, ind[a]fluorene, ind[a]carbazole, dibenzofuran, dibenzothiophene, benzo[a]carbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine, and triazine, wherein each of said groups is R 3 Replace; R 3 It has the definition given above or below.

[0046] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), L 11 To L 13 In each case, it is independently a single bond or benzene, naphthalene, fluorene, especially 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, spirodifluorene, phenanthrene, dibenzofuran, dibenzothiophene, or carbazole, which may be R by one or more groups. 3 Replace; R 3 It has the definition given above or below.

[0047] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), L 11 To L 13 In each case, it is independently a single bond or benzene, wherein each of the groups is replaced by a group R. 3 Replace; R 3 It has the definition given above or below.

[0048] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), L 1 and L 2 In each case, it is independently a single bond or derived from Ar. L -1 to Ar L -96 indicates one of the following; preferably a single bond or Ar... L -1 to Ar L -3 and Ar L -79 indicates:

[0049]

[0050]

[0051]

[0052]

[0053]

[0054] In Ar L -1 to Ar L -96 in, The dashed line is a connection to the corresponding residue of formula (1) or (2); Formula Ar L -1 to Ar L Each of -96 can be R 3 The substitution is made, and preferably, only H is present in the positions shown as unsubstituted, or H is partially or completely replaced by D in the positions shown as unsubstituted; R 3 It has the definition given above or below; Wherein group R 3 The two rings in the equation can form a monocyclic or polycyclic aliphatic or aromatic ring system, which can be substituted by one or more groups R'; and R' has the definition given above or below.

[0055] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), i11 to i13 represent 1, 2 or 3 in each occurrence.

[0056] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), i13 is 1 and L 13 It is a single bond or benzene, wherein each of the groups is replaced by a R group. 3 Replace; R 3 It has the definition given above or below.

[0057] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), the compound satisfies at least one of conditions 1-1 to 1-3: <Condition 1-1> i11 is 1 and L 11 It's a single key. <Condition 1-2> i12 is 1 and L 12 It's a single key. <Conditions 1-3> i13 is 1 and L 13 It is a single key.

[0058] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), R 1 Each occurrence may represent H, D, F, Cl, Br, I, CHO, CN, N(R) in the same or different ways. 4 )2,C(=O)R 4 , P(=O)(R 4 )2,S(=O)R 4 S(=O)2R 4 NO2, Si(R) 4 )3, B(OR 4 )2, OSO2R 4 The groups are straight-chain alkyl, alkoxy, or thioalkyl groups having 1 to 40 carbon atoms, or branched or cyclic alkyl, alkoxy, or thioalkyl groups having 3 to 40 carbon atoms, each of which may be further classified by one or more groups R. 4 Substitution, wherein in each case one or more non-adjacent CH2 groups may be replaced by R 4 C=CR 4 C≡C, Si(R) 4 )2、Ge(R 4 )2、Sn(R 4 )2. C=O, C=S, C=Se, P(=O)(R 4 ), SO, SO2, O, S or CONR 4 The aromatic or heteroaromatic ring system having 5 to 60 ring atoms, wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN, or NO2, and in each case the aromatic or heteroaromatic ring system may be replaced by one or more R groups. 4 Substitution, or an aryloxy group having 5 to 60 ring atoms, said aryloxy group may be replaced by one or more R groups. 4 Substitution, wherein the group R 1 The two components can form aliphatic or aromatic ring systems that are monocyclic or polycyclic, and these systems can be converted by one or more groups R. 4 Replace. R 4 It has the definition given above or below.

[0059] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), R1 Each occurrence is selected from H, D, F, CN, Si(R) in the same or different manner. 4 )3, N(R 4 )2, 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, each of which may be further classified by one or more groups R 4 Substitution, wherein in each case one or more non-adjacent CH2 groups may be replaced by R 4 C=CR 4 Alternatively, C≡C can be used instead, for aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, wherein in each case, the aromatic ring system and heteroaromatic ring system may be replaced by one or more groups R. 4 The aryloxy group is substituted, or has 6 to 40 aromatic ring atoms, wherein in each case it may be replaced by one or more R groups. 4 Replacement. Preferably, R 1 Each occurrence is selected, either identically or differently, from H, D, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, wherein the aromatic ring systems and heteroaromatic ring systems may in each case be represented by one or more groups R. 4 Replacement. More preferably, R 1 Each occurrence is identically or differently selected from H, D, and aromatic ring systems having 6 to 40 aromatic ring atoms, wherein the aromatic ring system may in each case be represented by one or more groups R. 4 Replace. R 4 It has the definition given above or below.

[0060] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), R 2 Each occurrence may represent H, D, F, Cl, Br, I, CHO, CN, N(R) in the same or different ways. 5 )2,C(=O)R 5 , P(=O)(R 5 )2,S(=O)R 5 S(=O)2R 5 NO2, Si(R) 5 )3, B(OR 5 )2, OSO2R 5 The groups are straight-chain alkyl, alkoxy, or thioalkyl groups having 1 to 40 carbon atoms, or branched or cyclic alkyl, alkoxy, or thioalkyl groups having 3 to 40 carbon atoms, each of which may be further classified by one or more groups R. 5Substitution, wherein in each case one or more non-adjacent CH2 groups may be replaced by R 5 C=CR 5 C≡C, Si(R) 5 )2、Ge(R 5 )2、Sn(R 5 )2. C=O, C=S, C=Se, P(=O)(R 5 ), SO, SO2, O, S or CONR 5 The aromatic or heteroaromatic ring system having 5 to 60 ring atoms, wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN, or NO2, and in each case the aromatic or heteroaromatic ring system may be replaced by one or more R groups. 5 Substitution, or an aryloxy group having 5 to 60 ring atoms, said aryloxy group may be replaced by one or more R groups. 5 Substitution, wherein the group R 2 and R 5 The two rings in R do not form a monocyclic or polycyclic aliphatic ring system or an aromatic ring system. 5 It has the definition given above or below.

[0061] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), R 2 Each occurrence is selected from H, D, F, CN, Si(R) in the same or different manner. 5 )3, N(R 5 )2, 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, each of said groups being surrounded by one or more R groups. 5 Substitution, wherein in each case one or more non-adjacent CH2 groups may be replaced by R 5 C=CR 5 Alternatively, C≡C can be used instead, for aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, wherein in each case, the aromatic ring system and heteroaromatic ring system may be replaced by one or more groups R. 5 The aryloxy group is substituted, or has 6 to 40 aromatic ring atoms, wherein in each case it may be replaced by one or more R groups. 5 Replacement. Preferably, R 2 Each occurrence is selected, either identically or differently, from H, D, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, wherein the aromatic ring systems and heteroaromatic ring systems may in each case be represented by one or more groups R. 5 Replacement. More preferably, R 2Each occurrence is identically or differently selected from H, D, and aromatic ring systems having 6 to 40 aromatic ring atoms, wherein the aromatic ring system may in each case be represented by one or more groups R. 5 Replace. R 5 It has the definition given above or below.

[0062] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), n2 represents an integer selected from 1 to 14 each time it appears.

[0063] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), R 3 To R 6 Each occurrence may represent H, D, F, Cl, Br, I, CHO, CN, N(Ar)2, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R')3, B(OR')2, OSO2R ´ 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, each of which may be substituted by one or more groups R', wherein in each case one or more non-adjacent CH2 groups may be substituted by R'C=CR', C≡C, Si(R')2, Ge(R')2, Sn(R')2, C=O, C=S, C=Se, P(=O)(R'), SO, SO2, O, S, or CONR', and wherein one or more H atoms may be substituted by D, F, Cl, Br, I, CN, or NO2; an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, wherein in each case the aromatic or heteroaromatic ring system may be substituted by one or more groups R', or an aryloxy group having 5 to 60 ring atoms, wherein the aryloxy group may be substituted by one or more groups R', wherein group R 3 R 4 and R 6 The two components can form aliphatic or aromatic ring systems, which are monocyclic or polycyclic, and these systems can be substituted by one or more groups R'. R' has the definition given above or below.

[0064] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole transport material comprising at least one compound represented by formula (1), R 3 To R 6Each occurrence may represent H, D, F, Cl, Br, I, CHO, CN, N(Ar)2, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R')3, B(OR')2, OSO2R ´ 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, each of which may be substituted by one or more groups R', wherein in each case one or more non-adjacent CH2 groups may be substituted by R'C=CR', C≡C, Si(R')2, Ge(R')2, Sn(R')2, C=O, C=S, C=Se, P(=O)(R'), SO, SO2, O, S, or CONR', and wherein one or more H atoms may be substituted by D, F, Cl, Br, I, CN, or NO2; an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, wherein in each case the aromatic or heteroaromatic ring system may be substituted by one or more groups R', or an aryloxy group having 5 to 60 ring atoms, wherein the aryloxy group may be substituted by one or more groups R', wherein group R 3 R 4 and R 6 The two components can form aliphatic or aromatic ring systems, either monocyclic or polycyclic, wherein the aliphatic or aromatic ring system can be substituted by one or more groups R'. Preferably, R' 3 To R 6 Each occurrence is identically or differently selected from H, D, and aromatic or heteroaromatic ring systems having 5 to 60 ring atoms, wherein the aromatic or heteroaromatic ring system may be substituted with one or more groups R' in each case. More preferably, R 3 To R 6 Each occurrence is selected, either identically or differently, from H, D, and aromatic ring systems having 6 to 40 aromatic ring atoms, wherein each aromatic ring system may be substituted by one or more groups R' in each case. R' has the definition given above or below.

[0065] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), Ar 11 and Ar 12 Each occurrence may refer to an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, which in each case may be represented by one or more groups R. 6 Substitution, in which two adjacent substituents Ar 11 and Ar 12 It can form monocyclic or polycyclic aliphatic or aromatic ring systems, which can be formed by one or more groups R.6 Replace. R 6 It has the definition given above or below.

[0066] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), Ar 11 and Ar 12 Each occurrence is identical or different from the monovalent groups derived from the following compounds: benzene, biphenyl, terphenyl, tetraphenyl, naphthalene, phenanthrene, fluorene, especially 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzo[a]fluorene, spirodifluorene, ind[a]fluorene, ind[a]carbazole, dibenzofuran, dibenzothiophene, benzo[a]carbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine, and triazine, wherein each of said groups is R-shaped by one or more R groups. 6 Replacement. Preferably, Ar 11 and Ar 12 Each time it appears, it is selected from phenyl, biphenyl, terphenyl, tetraphenyl, naphthalene, phenanthrene, fluorene, especially 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzo[a]fluorene, spirodifluorene, ind[a]fluorene, ind[a]carbazole, dibenzofuran, spiroxane, dibenzothiophene, benzo[a]carbazole, carbazole, benzofuran, and benzothiophene, wherein each of said groups is surrounded by one or more R groups. 6 Replace. R 6 It has the definition given above or below.

[0067] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), Ar 11 and Ar 12 At least one of them is an aromatic ring system having 5 to 60 ring atoms, and in each case, the aromatic ring system may also be converted by one or more groups R. 6 Replace, R 6 It has the definition given above or below.

[0068] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), Ar 11 and Ar 12 The groups selected from the following formula, either identically or differently each time they appear:

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083] The dashed lines represent bonds connected to nitrogen atoms, and the groups at the positions shown as unsubstituted can be R. 6 The group is substituted, and preferably only H is present in the position shown as unsubstituted, or H is partially or completely replaced by D in the position shown as unsubstituted.

[0084] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), Ar 11 and Ar 12 They are the same or different from each other.

[0085] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), wherein the compound represented by formula (1) comprises at least one deuterium.

[0086] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), the compound may be partially or completely replaced by deuterium.

[0087] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), wherein the compound satisfies at least one of conditions 2-1 to 2-7: <Condition 2-1> At least one R 1 Contains at least one deuterium, <Condition 2-2> At least one R 2 Contains at least one deuterium, <Condition 2-3> L 11 Contains at least one deuterium, <Condition 2-4> L 12 Contains at least one deuterium, <Condition 2-5> L 13 Contains at least one deuterium, <Condition 2-6> Ar 11 Contains at least one deuterium, <Condition 2-7> Ar 12 It contains at least one deuterium.

[0088] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), wherein the compound satisfies at least one of conditions 3-1 to 3-6: <Condition 3-1> At least one R 1 It is deuterium. <Condition 3-2> At least one R 2 It is deuterium. <Condition 3-3> At least one R 3 It is deuterium. <Condition 3-4> At least one R 4 It is deuterium. <Condition 3-5> At least one R 5 It is deuterium. <Condition 3-6> At least one R 6 It is deuterium.

[0089] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), wherein the compound satisfies at least one of conditions 4-1 to 4-6: <Condition 4-1> All R 1 They are all deuterium. <Condition 4-2> All R2 They are all deuterium. <Condition 4-3> All R 3 They are all deuterium. <Condition 4-4> All R 4 They are all deuterium. <Condition 4-5> All R 5 They are all deuterium. <Condition 4-6> All R 6 They are all deuterium.

[0090] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), Ar, in each occurrence, represents an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which in each case may also be substituted by one or more groups R'. R' has the definition given above or below.

[0091] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), R ´ Each time it appears, it may be represented by H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy, or thioalkyl having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl having 3 to 20 C atoms, wherein in each case one or more non-adjacent CH2 groups may be replaced by SO, SO2, O, S, and wherein one or more H atoms may be replaced by D, F, Cl, Br, or I, or an aromatic or heteroaromatic ring system having 5 to 24 ring atoms.

[0092] In one embodiment of the compound represented by formula (1) or in a preferred embodiment of a hole-transporting material comprising at least one compound represented by formula (1), R 1 To R 6 Ar is selected from the following formulas R-1 to R-187, either identically or differently, and Ar is selected from the following formulas R-1 to R-139 and R-179 to R-182, either identically or differently, in each occurrence:

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102] The following compounds are examples of compounds represented by formula (1):

[0103]

[0104]

[0105]

[0106]

[0107]

[0108] Compounds according to formula (1) can be prepared by synthetic methods such as oxidation, nucleophilic addition / substitution reactions, Buchwald coupling, and Suzuki coupling. Those skilled in the art, based on their general knowledge of organic synthetic chemistry, are aware of a variety of feasible synthetic routes.

[0109] Therefore, this application provides a method for preparing compounds according to this application, characterized in that 1) a carbonyl compound is generated by oxidation, 2) a substituted or unsubstituted biphenyl is introduced by nucleophilic addition, 3) cyclization, 4) a secondary amine is introduced by Buchwald reaction, or 5) in the case of an aryl linker, an amine having a linker is introduced by Suzuki reaction.

[0110] The above synthesis scheme is exemplified below: Option 1

[0111] Option 2

[0112] The first step is in the first row, the second step is in the second row, and the variable groups are defined as follows: X 1 X 2 and X 3 The groups are selected from reactive groups, preferably Cl, Br, I and sulfonyl groups, or similarly or differently. R 1 R 2 Ar 11 and Ar 12 It has the definition given above or below.

[0113] In one embodiment, a method for preparing a compound represented by formula (1) is provided, characterized in that a fluorenyl compound having at least one reactive group is reacted a) with a secondary amine in a Buchwald reaction, or b) with a boronic acid-substituted tertiary amine in a Suzuki reaction, or c) reacted in the following order: first i) with a boronic acid-substituted and halogen-substituted aromatic or heteroaromatic compound in a Suzuki reaction, and then ii) the resulting intermediate is reacted with a secondary amine in a Buchwald reaction.

[0114] By following these procedures, high purity, preferably exceeding 99.9%, can be achieved, if necessary, through purification such as recrystallization or sublimation. 1 The compound represented by formula (1) was obtained by determination by 1H NMR and / or HPLC.

[0115] For processing the compounds of the present invention from the liquid phase, for example by spin coating or printing, formulations of the compounds of the present invention are required. These formulations may be, for example, solutions, dispersions, or emulsions. For this purpose, the use of a mixture of two or more solvents is preferred. Suitable and preferred solvents are, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, tetrahydronaphthalene, veratrine, THF, methyl-THF, THP, chlorobenzene, dimethylbenzene, phenoxytoluene, especially 3-phenoxytoluene, (-)-fenone, 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-terpenes. Alcohols, benzothiazoles, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decahydronaphthalene, dodecylbenzene, ethyl benzoate, indene, methyl benzoate, NMP, p-cymene, phenethyl ether, 1,4-diisopropylbenzene, diphenylmethyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, or mixtures of these solvents.

[0116] Similarly, the present invention also provides a formulation, particularly a solution, dispersion, or emulsion, comprising at least one compound of the present invention as described above or a mixture of the present invention as described above, and at least one solvent, preferably an organic solvent. Methods for preparing such solutions are known to those skilled in the art.

[0117] The compound represented by formula (1) is suitable for electronic devices, particularly organic light-emitting diodes (OLEDs). Depending on the substitution, the compound represented by formula (1) can be used in different functions and layers. It is preferably used as a hole-transporting material in a hole-transporting layer and / or a matrix material in a light-emitting layer, and more preferably in combination with a phosphorescent emitter.

[0118] Therefore, the present invention also provides the use of the compound represented by formula (1) in electronic devices. The electronic device is preferably selected from organic integrated circuits (OIC), organic field-effect transistors (OFET), organic thin-film transistors (OTFT), organic light-emitting transistors (OLET), organic solar cells (OSC), organic optical detectors, organic photoreceptors, organic field quenching devices (OFQD), organic light-emitting electrochemical cells (OLEC), organic laser diodes (O-lasers), and more preferably organic electroluminescent devices (OLED).

[0119] The present invention also provides an electronic device comprising at least one compound represented by formula (1). The electronic device is preferably selected from the above-described devices.

[0120] A particularly preferred organic electroluminescent device comprises an anode, a cathode, and at least one light-emitting layer, characterized in that the device contains at least one organic layer comprising at least one compound represented by formula (1). A preferred organic electroluminescent device comprises an anode, a cathode, and at least one light-emitting layer, characterized in that at least one organic layer selected from a hole transport layer and a light-emitting layer comprises at least one compound represented by formula (1).

[0121] The hole transport layer is understood herein to refer to all layers disposed between the anode and the light-emitting layer, preferably a hole injection layer, a hole transport layer, and an electron blocking layer. The hole injection layer is understood herein to be a layer directly adjacent to the anode. The hole transport layer is understood herein to be a layer located between the anode and the light-emitting layer but not directly adjacent to the anode, and preferably not directly adjacent to the light-emitting layer either. The electron blocking layer is understood herein to be a layer located between the anode and the light-emitting layer and directly adjacent to the light-emitting layer. The electron blocking layer preferably has a high-energy LUMO, thus preventing electrons from leaving the light-emitting layer.

[0122] In addition to the cathode, anode, and light-emitting layer, the electronic device may also include other layers. For example, in each case, these layers are selected from one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, electron blocking layers, exciton blocking layers, intermediate layers, charge generation layers, and / or organic or inorganic p / n junctions. However, it should be noted that not every one of these layers is necessary, and the choice of layers always depends on the compound used, and in particular on whether the device is a fluorescent or phosphorescent photoluminescent device.

[0123] The preferred order of the layers in the electronic device is as follows: - Anode - - Hole injection layer - - Hole transport layer - - Optional other hole transport layers - - Emissive layer - - Optional hole-blocking layer - - Electron transport layer - - Electron injection layer - - Cathode -.

[0124] 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 exist.

[0125] The organic electroluminescent device of the present invention may contain two or more emissive layers. More preferably, these emissive layers generally have multiple emission peaks between 380 nm and 750 nm, such that the overall result is white light emission; in other words, multiple luminescent compounds that can emit fluorescence or phosphorescence and emit blue, green, yellow, orange, or red light are used in the emissive layers. A three-layer system is particularly preferred, i.e., a system having three emissive layers, wherein in each case one of the three layers exhibits blue light emission, in each case one of the three layers exhibits green light emission, and in each case one of the three layers exhibits orange or red light emission. Here, the compounds of the present invention are preferably present in the hole transport layer or the emissive layer. It should be noted that, in order to produce white light, it is also suitable to use only an emissive compound that emits light over a wide wavelength range, rather than using multiple luminescent compounds of various colors.

[0126] Preferably, the compound represented by formula (1) is used as the hole transport material. Here, the luminescent layer can be a fluorescent luminescent layer or a phosphorescent luminescent layer. The luminescent layer is preferably a blue fluorescent layer or a green phosphorescent layer.

[0127] When the device containing the compound represented by formula (1) contains a phosphorescent light-emitting layer, the layer preferably contains two or more, preferably exactly two different matrix materials (mixed matrix system). Preferred embodiments of the mixed matrix system will be described in detail below.

[0128] If the compound represented by formula (1) is used as a hole transport material in a hole transport layer, a hole injection layer or an electron blocking layer, the compound can be used as a pure material (i.e., in 100% proportion) in the hole transport layer, or it can be used in combination with one or more other compounds.

[0129] In a preferred embodiment, the hole-transporting layer comprising the compound represented by formula (1) further comprises one or more other hole-transporting compounds. These other hole-transporting compounds are preferably selected from triarylamine compounds, more preferably from monotriarylamine compounds. They are most preferably selected from preferred embodiments of the hole-transporting materials specified below. In a preferred embodiment described, the compound represented by formula (1) and the one or more other hole-transporting compounds are preferably each present in a proportion of at least 10%, more preferably in a proportion of at least 20%.

[0130] In a preferred embodiment, the hole-transporting layer comprising the compound represented by formula (1) further contains one or more p-dopers. The p-doper used according to the invention is preferably an organic electron acceptor compound capable of oxidizing one or more other compounds in the mixture.

[0131] As p-dopers, particularly preferred are quinone dimethane compounds, azidoindofluorene dione, azidothione, azidotriphenylide, I2, metal halides, preferably transition metal halides, metal oxides, preferably metal oxides containing at least one transition metal or Group 3 metal, and transition metal complexes, preferably complexes of Cu, Co, Ni, Pd, and Pt with ligands containing at least one oxygen atom as a binding site. Further preferred dopers are transition metal oxides, preferably oxides of rhenium, molybdenum, and tungsten, more preferably Re2O7, MoO3, WO3, and ReO3. Further preferred are bismuth complexes in the (III) oxidation state, more particularly complexes of bismuth (III) with electron-deficient ligands, more particularly carboxylic acid anion ligands.

[0132] The p-dopant is preferably distributed substantially uniformly in the p-doped layer. This can be achieved, for example, by co-evaporation of the p-dopant and the hole transport material matrix. The p-dopant is preferably present in the p-doped layer at a concentration of 1% to 10%.

[0133] Furthermore, the preferred p-dopants are the compounds explicitly disclosed in the table on pages 86-87 of WO2021 / 156323A1.

[0134] In a preferred embodiment, the device contains a hole injection layer conforming to one of the following embodiments: a) it contains a triarylamine and a p-dopant; or b) it contains a single electron-deficient material (electron acceptor). In a preferred embodiment of embodiment a), the triarylamine is a monotriarylamine, particularly one of the preferred triarylamine derivatives mentioned below. In a preferred embodiment of embodiment b), the electron-deficient material is a hexaazatriphenylide derivative as described in US 2007 / 0092755.

[0135] The compound represented by formula (1) may be present in the hole injection layer, hole transport layer, and / or electron blocking layer of the device. When the compound is present in the hole injection layer or hole transport layer, it is preferably p-doped, which means that it is in a mixed form with the p-dopant as described above in the layer.

[0136] The compound represented by formula (1) is preferably present in the electron blocking layer. In this case, it is preferably not p-doped. More preferably, in this case, it is preferably in the form of a single compound in the layer without the addition of other compounds.

[0137] In another preferred embodiment, the compound represented by formula (1) is used as a matrix material in combination with one or more luminescent compounds (preferably phosphorescent compounds) in the luminescent layer. Here, the phosphorescent compound is preferably selected from red phosphorescent and green phosphorescent compounds.

[0138] In this case, the proportion of the matrix material in the light-emitting layer is between 50.0 vol% and 99.9 vol%, preferably between 80.0 vol% and 99.5 vol%, and more preferably between 85.0 vol% and 97.0 vol%.

[0139] Accordingly, the proportion of the luminescent compound is between 0.1 vol% and 50.0 vol%, preferably between 0.5 vol% and 20.0 vol%, and more preferably between 3.0 vol% and 15.0 vol%.

[0140] The luminescent layer of an organic electroluminescent device may also contain a system comprising multiple matrix materials (a mixed matrix system) and / or multiple luminescent compounds. In this case, the luminescent compound is typically a smaller proportion of the compound in the system, while the matrix material is a larger proportion. However, in some cases, the proportion of a single matrix material in the system may be less than the proportion of a single luminescent compound.

[0141] Preferably, the compound represented by formula (1) is used as a component of the mixed matrix system, and more preferably as a component of the mixed matrix system of the phosphorescent emitter. The mixed matrix system preferably includes two or three different matrix materials, more preferably two different matrix materials. Preferably, in this case, one of the two materials is a material with hole transport properties, and the other is a material with electron transport properties. More preferably, one of the materials is selected from compounds with a large energy difference between HOMO and LUMO (wide bandgap material). In the mixed matrix system, the compound represented by formula (1) is preferably a matrix material with hole transport properties. Accordingly, when the compound represented by formula (1) is used as the matrix material of the phosphorescent emitter in the OLED light-emitting layer, a second matrix compound with electron transport properties is present in the light-emitting layer. Here, the two different matrix materials can exist in a ratio of 1:50 to 1:1, preferably 1:20 to 1:1, more preferably 1:10 to 1:1, and most preferably 1:4 to 1:1.

[0142] However, the desired electron transport and hole transport characteristics of the mixed matrix components can also be primarily or entirely combined in a single mixed matrix component, in which case the other mixed matrix components perform other functions.

[0143] Preferably, the following material categories are used in the above-described layers of the device: Phosphorescent light source: The term "phosphorescent emitter" generally refers to compounds that achieve light emission through spin-forbidden transitions, such as from an excited triplet state or a state with a higher spin quantum number, such as a quintet state.

[0144] Suitable phosphorescent emitters, especially those that emit light in the visible light region when properly excited, and which contain at least one compound with an atomic number greater than 20, preferably greater than 38 and less than 84, more preferably greater than 56 and less than 80. As phosphorescent emitters, compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium are preferred, especially compounds containing iridium, platinum, or copper.

[0145] In the context of this invention, all luminescent iridium, platinum, or copper complexes are considered phosphorescent compounds.

[0146] Generally, all phosphorescent complexes known to those skilled in the art of phosphorescent OLEDs and organic electroluminescent devices are suitable for the devices of the present invention. Other examples of suitable phosphorescent emitters are those shown in the tables on pages 100-104 of WO2023 / 025971A2.

[0147] Fluorescent light source: Preferred fluorescent compounds are selected from arylamines. In the context of this invention, arylamines or aromatic amines are understood to mean 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 ring atoms. Preferred examples are aromatic anthraceneamines, aromatic anthracene diamines, aromatic pyreneamines, aromatic pyrene diamines, aromatic pyrine amines, or aromatic pyrine diamines. Aromatic anthraceneamines are understood to mean compounds in which a diaryl amino group is directly bonded to anthracene, preferably at the 9 position. Aromatic anthracene diamines are understood to mean compounds in which two diaryl amino groups are directly bonded to anthracene, preferably at the 9 or 10 positions. The definitions of aromatic pyreneamines, pyrene diamines, pyrine amines, and pyrine diamines are similar, wherein the diaryl amino group is preferably bonded to pyrene at the 1 or 1,6 position. Further preferred luminescent compounds are indenefluoreneamine or indenefluorene diamine, benzo[a]indenefluoreneamine or benzo[a]indenefluorene diamine and dibenzo[a]indenefluoreneamine or dibenzo[a]indenefluorene diamine, as well as indenefluorene derivatives having fused aryl groups. Pyrene arylamines are also preferred. Also preferred are benzo[a]indenefluoreneamine, benzo[a]fluoreneamine, extended benzo[a]indenefluorene, phenazine, and fluorene derivatives linked to furan or thiophene units.

[0148] Matrix materials for phosphors: Preferred matrix materials for phosphors are selected from oligoarylene groups (e.g., 2,2',7,7'-tetraphenylspirodifluorene), particularly oligoarylene groups containing fused aromatic groups, oligoarylene vinylidene groups, multi-legged metal complexes, hole-conducting compounds, electron-conducting compounds, particularly ketones, phosphine oxides and sulfoxides, transisomers, boric acid derivatives, or benzanthracene. Particularly preferred matrix materials are selected from oligoarylene groups comprising naphthalene, anthracene, benzanthracene, and / or pyrene, or transisomers of these compounds, oligoarylene vinylidene groups, ketones, phosphine oxides, and sulfoxides. Very particularly preferred matrix materials are selected from oligoarylene groups comprising anthracene, benzanthracene, benzo[a]phenanthrene, and / or pyrene, or transisomers of these compounds. In the context of this invention, oligoarylene groups should be understood to mean compounds in which at least three aryl groups or arylene groups are bonded to each other.

[0149] Matrix materials for phosphorescent emitters: Preferred matrix materials for phosphorescent emitters, in addition to the compounds represented by formula (1), include aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, triarylamines, carbazole derivatives such as CBP (N,N-biscarbazole biphenyl) or carbazole derivatives, indole-carbazole derivatives, indo-carbazole derivatives, indo-carbazole derivatives, azacarbazole derivatives, bipolar matrix materials, silanes, borazine or borate esters, triazine derivatives, zinc complexes, diazacyclopentane or tetrazacyclopentane derivatives, phosphonodiazacyclopentane derivatives, bridged carbazole derivatives, biphenylide derivatives, or lactams.

[0150] Electron transport materials: Suitable electron transport materials 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.

[0151] The material used for the electron transport layer can be any material used as an electron transport material in the electron transport layer according to existing technology. Particularly suitable materials include aluminum complexes such as Alq3, zirconium complexes such as Zrq4, lithium complexes such as Liq, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, diazole derivatives, aromatic ketones, lactams, boranes, phosphazacyclopentane derivatives, and phosphine oxide derivatives.

[0152] Preferred electron transport and electron injection materials are those shown in the table on pages 73-75 of WO2020 / 109434A1.

[0153] Hole transport materials: In addition to the compounds of formula (1), other preferred compounds for the hole transport layer of the OLED of the present invention are indene-fluoreneamine derivatives, amine derivatives, hexaazatriphenylide derivatives, amine derivatives having a fused aromatic system, monobenzo-indenefluoreneamine, dibenzo-indenefluoreneamine, spirodifluoreneamine, fluoreneamine, spirodibenzopyranamine, dihydroacridine derivatives, spirodibenzofuran and spirodibenzothiophene, phenanthrene diarylamine, spirotribenzotropeneone, spirodifluorene having a m-phenylenediamine group, spirodiacridine, xanthondiarylamine, and 9,10-dihydroanthracene spirospirone having a diarylamino group. Preferred hole transport compounds are those shown in the table on pages 76-80 of WO2020 / 109434A1.

[0154] The preferred cathode of the electronic device is a metal with low work function, a metal alloy composed of various metals, or a multilayer structure, such as alkaline earth metals, alkali metals, main group metals, or lanthanides (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Also suitable are alloys composed of alkali metals or alkaline earth metals and silver, such as alloys composed of magnesium and silver. In the case of a multilayer structure, in addition to the metals mentioned above, other metals with relatively high work functions, such as Ag or Al, may be used. 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 useful materials for this purpose are alkali metal or alkaline earth metal fluorides, but also include the 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 layer thickness is preferably between 0.5 and 5 nm.

[0155] 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 preferred. x Al / PtO x Alternatively, an anode may be preferred. For some applications, at least one electrode must be transparent or partially transparent to allow illumination of organic materials (organic solar cells) or light emission (OLED, O-LASER). Here, the preferred anode material is a conductive mixed metal oxide. Indium tin oxide (ITO) or indium zinc oxide (IZO) are particularly preferred. Also preferred are conductive doped organic materials, especially conductive doped polymers. Furthermore, the anode may consist of two or more layers, for example, an ITO inner layer and a metal oxide outer layer, preferably tungsten oxide, molybdenum oxide, or vanadium oxide.

[0156] In a preferred embodiment, the electronic device is characterized in that one or more layers are coated by a sublimation process. In this case, the material is sublimated in a vacuum sublimation system at a concentration of less than 10⁻⁶. 5 millibars, preferably less than 10 -6 An initial pressure of millibars is applied via vapor deposition. However, in this case, the initial pressure can also be even lower, for example, less than 10. -7 millibar.

[0157] Also preferred is an electronic device characterized by one or more layers being coated by an OVPD (organic vapor deposition) method or by means of carrier gas sublimation. In this case, the material is in 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 Jet Printing) 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).

[0158] Another preferred electronic device is characterized by one or more layers being 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 (photo-induced thermal imaging, thermal transfer printing) or inkjet printing. For this purpose, a soluble compound of formula (1) is required. High solubility can be achieved through appropriate substitution of said compound.

[0159] Alternatively, the electronic device of the present invention is manufactured by applying one or more layers from a solution and by applying one or more layers by sublimation.

[0160] After the layer is applied, the device is structured, contacted, and finally sealed, depending on the application, to eliminate the damaging effects of water and air.

[0161] According to the present invention, the electronic device comprising one or more compounds of formula (1) can be used in displays, as a light source in lighting applications, and as a light source in medical and / or cosmetic applications.

[0162] Example

[0163] A) Synthetic Example

[0164] a) Synthesis of spirocyclic compounds

[0165] In a 500 mL round-bottom flask reactor, 2-bromo-4′-chloro-1,1′-biphenyl (24 g, 90 mmol) and tetrahydrofuran (300 mL) were cooled to -78 °C. At the same temperature, n-butyllithium (19.3 mL, 0.031 mol) was added dropwise to the reaction solution and stirred for 2 hours. Then, 12.5 g (94 mmol) of bicyclo[3.3.1]non-9-one (12.5 g, 94 mmol) in 200 mL of THF was added little by little to the reaction solution and stirred at room temperature. After complete conversion, the reaction was stopped with H₂O (50 mL) and extracted with ethyl acetate and water. The organic layer was separated, concentrated under vacuum, and recrystallized in acetonitrile to give an intermediate as a solid. This intermediate was redissolved in acetic acid (1000 mL) and HCl (94 mL) and stirred under reflux for 5 hours. After complete conversion of the intermediate, the reaction mixture was cooled to room temperature and filtered. Further purification was achieved by recrystallization from toluene / heptane. (23 g, 76 mmol, 85%)

[0166] The following compounds can be obtained in a similar manner and with similar yields:

[0167] b) Amine synthesis

[0168] In a 2500 mL round-bottom flask under an argon atmosphere, a mixture of compound (a) (40 g, 130 mmol; 1.00 equivalent), N-[1,1′-biphenyl]-4-yl-N-(4-bromophenyl)-9,9-dimethyl-9H-fluorene-2-amine (67 g, 130 mmol; 1.00 equivalent), and sodium tert-amyloxide [CAS 14593-46-5] (15.9 g, 144 mmol; 1.10 equivalent) was placed in 2000 mL toluene. Dicyclohexyl-(2',6'-dimethoxy-biphenyl-2-yl)-phosphine (SPhos) (1.62 mg, 3.94 mmol; 3 mol%) and palladium acetate [3375-31-3] (886 mg, 3.99 mmol; 3 mol%) were added, and the mixture was heated to reflux for 18 hours. After complete conversion and cooling to room temperature, water was added to the reaction. Following phase separation and extraction of the aqueous phase with toluene, the combined organic phases were concentrated and heptane was added. The precipitated solid was separated. Purification using Soxhlet extraction, recrystallization, and vacuum sublimation yielded the desired product (46 g, 78 mmol, 60%).

[0169] The following compounds can be obtained in a similar manner and with similar yields:

[0170] c) Synthesis of boric acid

[0171] Compound (a) (83 g, 270 mmol) was dissolved in 1500 mL of anhydrous diethyl ether and cooled to -78 °C. At this temperature, n-butyllithium (110 mL, 270 mmol, 2.5 M) was added over approximately 10 min, followed by stirring at -78 °C for another 30 min. Trimethyl borate (40 mL, 351 mmol) was added as quickly as possible at this temperature, allowing the reaction to slowly reach room temperature (approximately 18 h). The reaction solution was washed with water, and the precipitated solid and organic phase were azeotropically dried over toluene. The crude product was washed by stirring with toluene / dichloromethane and filtration at approximately 40 °C. The residue was purified by recrystallization from toluene / heptane (76 g, 240 mmol, 89%).

[0172] The following compounds can be obtained in a similar manner and with similar yields:

[0173] d) Suzuki reaction:

[0174] Structure (f) core

[0175] Compound (c) (20 g, 63 mmol), potassium phosphate monohydrate, compound (f) (21.1 g, 94 mmol), and XPhos Palladacylce Gen.3 (1.6 g, 1.9 mmol) were dissolved in 60 mL THF / water (4:1) and stirred at 60 °C for 16 h. The mixture was cooled to room temperature and diluted with toluene and H2O. The organic phase was collected, and the aqueous phase was further extracted with toluene. The combined organic phases were washed with brine, collected, dehydrated with Na2SO4, filtered, and concentrated. The resulting residue was placed in 1 L EtOH and stirred vigorously until a free-flowing precipitate formed. The precipitate was collected by filtration and washing with ethanol. The material was transferred to DCM and filtered through SiO2 (toluene / heptane 1:1). The filtrate was concentrated to dryness (29 g, 44 mmol, 70%).

[0176] The following compounds can be obtained in a similar manner and with similar yields:

[0177] e) Deuteration

[0178] Compound (d) (20.3 g, 30.4 mmol), benzene-D6 (120 ml), and trifluoromethanesulfonic acid (19 ml, 212 mmol) were added to a flask and stirred at 60 °C for 4 hours. Then, 600 ml of distilled water and NaHCO3 were added dropwise. The organic layer was then extracted with MgSO4. Water was removed beforehand. The concentrated organic layer was purified by silica gel extraction. Finally, it was sublimed (10... -6 The product was obtained as a solid after (20 g, 28.5 mmol, 93%).

[0179] The following compounds can be obtained in a similar manner and with similar yields:

[0180] B) Device Examples

[0181] 1) General manufacturing methods and characterization of OLEDs

[0182] A glass plate coated with 50 nm thick structured ITO (indium tin oxide) is the substrate for applying OLEDs.

[0183] The OLED essentially has the following layer structure: substrate / hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / emitting layer (EML) / electron transport layer, optionally with a second layer (ETL) / 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 found in the table below. The materials used to produce the OLED are shown in the table below.

[0184] All materials are applied in a vacuum chamber via thermal vapor deposition. In this case, the luminescent layer consists of at least one matrix material (host material) and luminescent dopants added to the matrix material in a specific volume ratio via co-evaporation. Here, details given in the form of H:SEB (95%:5%) mean that material H is present in the layer at a volume ratio of 95% and SEB at a ratio of 5%.

[0185] Similarly, the electron transport layer and hole injection layer are also composed of a mixture of two materials. The structures of the materials used in the OLED are shown in Table 1.

[0186] The OLED was characterized in a standard manner. For this purpose, the electroluminescence spectrum was determined, and the external quantum efficiency (EQE, measured as a percentage) and lifetime as a function of luminance were calculated from the current-voltage-luminance characteristics under the assumption of Lambertian light emission properties. The parameter EQE @ 10 mA / cm² refers to the external quantum efficiency achieved at 10 mA / cm². The parameter U @ 10 mA / cm²... 2 This refers to 10mA / cm 2 The operating voltage is specified. Lifetime LT is defined as the time it takes for the brightness to decrease from its initial value to a certain percentage during operation at a constant current density. The LT80 figure here means that the reported lifetime corresponds to the time after the brightness has decreased to 80% of its initial value. Here, the number @60 or 40 mA / cm² indicates this. 2 This means that the lifetime in question is 60 or 40 mA / cm. 2 The measurement was taken below.

[0187]

[0188]

[0189] 1) The OLED of the present invention containing a compound of formula (1) in the EBL of a green phosphorescent OLED

[0190] The devices shown in the table below were manufactured:

[0191]

[0192] As can be seen in Table 3, the inventive compound HT-A in device 1 provides an improved voltage at similar efficiency compared to the comparative compound HT-B in device C1, and provides a significantly improved voltage at similar efficiency compared to the comparative compound HT-C in device C2.

[0193]

[0194] 2) The OLED of the present invention containing the compound of formula (1) in the HIL and HTL of the blue fluorescent OLED

[0195] The devices shown in the table below were manufactured:

[0196]

[0197] This type of OLED also achieves very good efficiency and lifespan.

[0198]

Claims

1. A compound represented by formula (1): Equation (1) Equation (2) The groups and markings that appear are as follows: X is the same or different in each case, and is N or CR. 1 One of X is CR 1 And R 1 It is a group represented by formula (2); It is the binding site between the group represented by formula (2) and formula (1); L 11 To L 13 Each occurrence may represent a single bond or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be represented by one or more R atoms. 3 Group substitution; i11 to i13 represent 1, 2 or 3 in each occurrence, either the same or different. R 1 Each occurrence may represent H, D, F, Cl, Br, I, CHO, CN, N(R) in the same or different ways. 4 )2,C(=O)R 4 , P(=O)(R 4 )2,S(=O)R 4 S(=O)2R 4 NO2, Si(R) 4 )3, B(OR 4 )2, OSO2R 4 The groups are straight-chain alkyl, alkoxy, or thioalkyl groups having 1 to 40 carbon atoms, or branched or cyclic alkyl, alkoxy, or thioalkyl groups having 3 to 40 carbon atoms, each of which may be further classified by one or more groups R. 4 Substitution, wherein in each case one or more non-adjacent CH2 groups may be replaced by R 4 C=CR 4 C≡C, Si(R) 4 )2、Ge(R 4 )2、Sn(R 4 )2. C=O, C=S, C=Se, P(=O)(R 4 ), SO, SO2, O, S or CONR 4 The aromatic or heteroaromatic ring system having 5 to 60 ring atoms, wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN, or NO2, and in each case the aromatic or heteroaromatic ring system may be replaced by one or more R groups. 4 Substitution, or an aryloxy group having 5 to 60 ring atoms, said aryloxy group may be replaced by one or more R groups. 4 Substitution, wherein the group R 1 The two components can form aliphatic or aromatic ring systems that are monocyclic or polycyclic, and these systems can be converted by one or more groups R. 4 replace; R 2 Each occurrence may represent H, D, F, Cl, Br, I, CHO, CN, N(R) in the same or different ways. 5 )2,C(=O)R 5 , P(=O)(R 5 )2,S(=O)R 5 S(=O)2R 5 NO2, Si(R) 5 )3, B(OR 5 )2, OSO2R 5 The groups are straight-chain alkyl, alkoxy, or thioalkyl groups having 1 to 40 carbon atoms, or branched or cyclic alkyl, alkoxy, or thioalkyl groups having 3 to 40 carbon atoms, each of which may be further classified by one or more groups R. 5 Substitution, wherein in each case one or more non-adjacent CH2 groups may be replaced by R 5 C=CR 5 C≡C, Si(R) 5 )2、Ge(R 5 )2、Sn(R 5 )2. C=O, C=S, C=Se, P(=O)(R 5 ), SO, SO2, O, S or CONR 5 The aromatic or heteroaromatic ring system having 5 to 60 ring atoms, wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN, or NO2, and in each case the aromatic or heteroaromatic ring system may be replaced by one or more R groups. 5 Substitution, or an aryloxy group having 5 to 60 ring atoms, said aryloxy group may be replaced by one or more R groups. 5 Substitution, wherein the group R 2 and R 5 The two aliphatic or aromatic ring systems that do not form monocyclic or polycyclic rings; n2 represents an integer selected from 1 to 14, either the same or different each time it appears; Ar 11 and Ar 12 Each occurrence may refer to an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, and in each case may also be represented by one or more R groups. 6 Substitution, in which two adjacent substituents Ar 11 and Ar 12 It can form monocyclic or polycyclic aliphatic or aromatic ring systems, which can be formed by one or more groups R. 6 replace, R 3 To R 6 Each occurrence may represent H, D, F, Cl, Br, I, CHO, CN, N(Ar)2, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R')3, B(OR')2, OSO2R ´ 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, each of which may be substituted by one or more groups R', wherein in each case one or more non-adjacent CH2 groups may be substituted by R'C=CR', C≡C, Si(R')2, Ge(R')2, Sn(R')2, C=O, C=S, C=Se, P(=O)(R'), SO, SO2, O, S, or CONR', and wherein one or more H atoms may be substituted by D, F, Cl, Br, I, CN, or NO2; an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, wherein in each case the aromatic or heteroaromatic ring system may be substituted by one or more groups R', or an aryloxy group having 5 to 60 ring atoms, wherein the aryloxy group may be substituted by one or more groups R', wherein group R 3 R 4 and R 6 The two aliphatic or aromatic ring systems in the ring can form monocyclic or polycyclic aliphatic or aromatic ring systems, wherein the aliphatic or aromatic ring system can be substituted by one or more groups R'; Ar, in each instance, may refer to an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which may in each case be substituted by one or more groups R'. R ´ Each time it appears, it may be represented by H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy, or thioalkyl having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl having 3 to 20 C atoms, wherein in each case one or more non-adjacent CH2 groups may be replaced by SO, SO2, O, S, and wherein one or more H atoms may be replaced by D, F, Cl, Br, or I, or an aromatic or heteroaromatic ring system having 5 to 24 ring atoms.

2. The compound according to claim 1, characterized in that... The compound is represented by at least one of formulas 1-1 to 1-4: X, L 11 To L 13 i11 to i13, R 2 n2, Ar 11 and Ar 12 It has the definition given in claim 1.

3. The compound according to claim 1 or 2, characterized in that... X is the same or different in every case, and is CR 1 .

4. The compound according to one or more of claims 1 to 3, characterized in that... The group represented by formula (2) is represented by formula 2-1 or 2-2: In equations 2-1 and 2-2, L 2 It is a single bond, N(R) 61 ), S, O, C(R) 61 (R) 62 ), C(R 61 )=C(R 62 ) or Si(R 61 (R) 62 ); i2 is 0 or 1; R 61 and R 62 Each independently refers to R in claim 1 6 Definition; L 11 To L 13 i11 to i13, R 6 Ar 11 and Ar 12 It has the definition given in claim 1.

5. The compound according to one or more of claims 1 to 4, characterized in that... L 11 To L 13 Each occurrence is identical or different from single bonds and divalent groups derived from the following substances: benzene, biphenyl, terphenyl, tetraphenyl, naphthalene, phenanthrene, fluorene, especially 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzo[a]fluorene, spirodifluorene, ind[a]fluorene, ind[a]carbazole, dibenzofuran, dibenzo[a]thiophene, benzo[a]carbazole, carbazole, benzo[a]furan, benzo[a]thiophene, indole, quinoline, pyridine, pyrimidine, pyrazinidazine, and triazine, wherein each of said groups may be derived from one or more R 3 Group substitution; R 3 It has the definition given in claim 1.

6. The compound according to one or more of claims 1 to 5, characterized in that... i13 is 1 and L 13 It is a single bond or benzene, wherein each of the groups can be bonded by one or more R 3 Group substitution; R 3 It has the definition given in claim 1.

7. The compound according to one or more of claims 1 to 6, characterized in that... The compound satisfies at least one of conditions 1-1 to 1-3: <Condition 1-1> i11 is 1 and L 11 It's a single key. <Condition 1-2> i12 is 1 and L 12 It's a single key. <Conditions 1-3> i13 is 1 and L 13 It is a single key.

8. The compound according to one or more of claims 1 to 7, characterized in that... Ar 11 and Ar 12 At least one of them is an aromatic ring system having 5 to 60 ring atoms, and in each case, the aromatic ring system may also be converted by one or more groups R. 6 Replace, R 6 It has the definition given in claim 1.

9. The compound according to one or more of claims 1 to 8, characterized in that... Ar 11 and Ar 12 They are the same or different from each other.

10. The compound according to one or more of claims 1 to 9, characterized in that... The compound contains at least one deuterium.

11. A method for producing a compound according to formula (1) according to one or more of claims 1 to 10, characterized in that... A fluorenyl compound having at least one reactive group is reacted a) with a secondary amine in a Buchwald reaction, or b) with a boronic acid-substituted tertiary amine in a Suzuki reaction, or c) reacted in the following order: first i) with a boronic acid-substituted and halogen-substituted aromatic or heteroaromatic compound in a Suzuki reaction, and then ii) the resulting intermediate is reacted with a secondary amine in a Buchwald reaction to give a compound according to formula (1) as claimed in one or more of claims 1 to 10.

12. A formulation comprising at least one compound according to one or more of claims 1 to 10 and at least one solvent.

13. An electronic device comprising at least one compound according to one or more of claims 1 to 10.

14. The electronic device according to claim 13, characterized in that... The electronic device is an organic electroluminescent device and contains an anode, a cathode and at least one light-emitting layer, and the compound is contained in the hole transport layer or the light-emitting layer of the device.

15. Use of the compound according to one or more of claims 1 to 10 in an electronic device.

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