Materials for electronic devices

Abstract

The present invention provides compounds having functional substituents in a specific spatial arrangement, devices containing said functional substituents, methods for producing the same, and uses thereof. The present invention relates to a compound represented by the following general formula (5). JPEG2022008530000121.jpg46170 X is CR 1 A and A' are the same or different and are aromatic ring structures having 6 ring atoms; ETG is an organic electron transport group (ETG) from the group of electron-deficient heterocyclic aromatic groups, ETG being selected from triazinyl groups, pyrimidyl groups, pyrazinyl groups, etc.; Z is a single bond or a divalent group; W is NR 1 , O or S, and R 4 are identical or different for each occurrence and in each case have one or more R 2 an aromatic ring having 6 to 60 aromatic ring atoms which may be substituted by a group, and R 1 , R 2 is H etc.

Description

[Technical Field]

[0001] This invention relates to cyclic compounds having specific arrangements of electron-conducting and hole-conducting groups, their use in electronic devices, methods for manufacturing them, and electronic devices.

[0002] The structures of organic electroluminescent devices (e.g., OLEDs - organic light-emitting diodes or OLECs - organic light-emitting electrochemical cells) in which organic semiconductors are used as functional materials are described, for example, in US 4539507, US 5151629, EP0676461 and WO98 / 27136. The light-emitting materials used here are increasingly organometallic complexes that exhibit phosphorescence, as well as fluorescence (MA Baldo et al., Appl. Phys. Lett. 1999, 75, 4-6). Due to quantum mechanical reasons, energy and power efficiencies of up to four times are possible using organometallic compounds as phosphorescent emitters. In general, there is still a need for improvement, particularly with respect to efficiency, drive voltage, and lifetime, in both the case of OLEDs exhibiting singlet emission and OLEDs exhibiting triplet emission. This is especially true for OLEDs that emit light in shorter wavelength ranges, i.e., green and especially blue.

[0003] The properties of an organic electroluminescent device are not determined solely by the emitter used. Other materials used, such as the host and matrix materials, hole-blocking materials, electron-transporting materials, and electron or exciton-blocking materials, are also particularly important. Improvements to these materials can therefore lead to significant improvements in the electroluminescent device.

[0004] According to the prior art, ketones (e.g., according to 2004 / 093207 or WO 2010 / 006680) or phosphine oxides (e.g., according to WO 2005 / 003253) are included in the matrix material used for phosphorescent emitters. Further matrix materials according to the prior art are triazines (e.g., WO 2008 / 056746, EP 0906947, EP 0908787, EP 0906948).

[0005] According to the prior art, for fluorescent OLEDs, condensed aromatics, in particular anthracene derivatives, in particular, 9,10-bis(2-naphthyl)anthracene (US 5935721) are used as host materials for blue electroluminescent devices. WO 03 / 095445 and CN 1362464 disclose 9,10-bis(1-naphthyl)anthracene derivatives for use in OLEDs. Further anthracene derivatives are disclosed in WO 01 / 076323, WO 01 / 021729, WO 2004 / 013073, WO 2004 / 018588, WO 2003 / 087023, or WO 2004 / 018587. Aryl-substituted pyrene and chrysene-based host materials are disclosed in WO 2004 / 016575. Benzanthracene derivative-based host materials are disclosed in WO 2008 / 145239. Having available improved host materials is desirable for high-value-added applications.

[0006] Prior art, for example, discloses the use of compounds containing one or more carbazole groups in electronic devices, as known in WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 288381, EP 1205527, or WO 2008 / 086851.

[0007] Prior art further discloses the use of compounds containing one or more indenocarbazole groups in electronic devices, as known, for example, in WO 2010 / 136109 and WO 2011 / 000455.

[0008] Prior art further discloses the use of compounds comprising one or more electron-deficient heterocyclic aromatic six-membered rings in electronic devices, as known, for example, in WO 2010 / 015306, WO 2007 / 063754 and WO 2008 / 056746.

[0009] WO 2009 / 069442 discloses tricyclic systems such as carbazoles, dibenzofurans, or dibenzothiophenes having a high level of substitution with electron-deficient heterocyclic aromatics (e.g., pyridine, pyrimidine, or triazine). The tricyclic systems are not substituted with hole-conducting groups, i.e., electron-rich groups.

[0010] JP 2009-21336 discloses a substituted carbazole as a matrix material, in which the carbazole is substituted with electron-conducting and hole-conducting groups. However, the compound does not have face-to-face substitution.

[0011] WO 2011 / 057706 discloses substituted carbazoles as matrix materials, in which the carbazole is substituted with electron-conducting and hole-conducting groups. However, most of the disclosed carbazoles do not have any face-to-face substitutions. In each of the disclosed face-to-face substitutions, however, the hole or electron-conducting group is directly bonded to the tricyclic system.

[0012] However, as with other materials, there is still a need for improvement in these materials, particularly regarding the efficiency and lifespan of the components.

[0013] Therefore, the object of the present invention is to provide compounds suitable for use in fluorescent or phosphorescent OLEDs, for example, as host and / or matrix materials, or as hole transport / electron blocking materials or exciton blocking materials, or as electron transport or hole blocking materials, which, when used in OLEDs, provide good device characteristics, and to provide corresponding electronic devices.

[0014] Surprisingly, certain compounds, described in detail below, have been found to achieve these objectives and, in particular, to yield good properties of organic electroluminescent devices with respect to lifetime, efficiency, and drive voltage. Therefore, electronic devices, in particular organic electroluminescent devices, comprising such compounds and corresponding preferred compounds are provided by the present invention. The remarkable effect is achieved in the compounds of the formulas listed below by a specific arrangement of electron-conducting groups and hole-conducting groups ("facing" i.e., an arrangement of groups opposite each other). Rapid charge transport is possible due to a relatively well-defined (highly ordered) parallel alignment (facing arrangement) of molecules, where there is a kind of short-range order of molecules, although this is not bound by theory. Intermolecular interactions due to short distances between groups, such as direct π-π interactions, may be one of the causes of rapid charge transfer.

[0015] The compounds of the present invention also have a high glass transition temperature (T g ) possesses advantages in terms of compound processing during electronic device manufacturing. The high glass transition temperature of the compound also allows for the use of the compound in thin amorphous organic layers.

[0016] Furthermore, the compounds of the present invention enable the stabilization of valence carriers in the excited state and possess a sufficiently high triplet energy, which is an important prerequisite for phosphorescent devices. Moreover, the compounds of the present invention have improved properties in OLEDs compared to compounds from the prior art.

[0017] Therefore, the present invention provides a compound of general formula (1),

[0018] [ka]

[0019] The symbols and subscripts used in the formula are as follows: A and A' may be identical or different, and may be independent of each other, and may be one or more R 1An aromatic or heteroaromatic ring structure having 5 or 6 ring atoms which may be substituted by a group; ETG is an organic electron transport group (ETG) selected from the group of electron-deficient heteroaromatic groups. ETG is preferably a heteroaryl group having 5 to 60 aromatic ring atoms, N is a very preferred heteroatom, and the most preferred ETGs are selected from the groups of triazine, pyrimidine, pyrazine, imidazole, benzimidazole and pyridine. The ETG group may be substituted by one or more independent R 1 groups; Z is a single bond or a divalent group; when Z is a single bond, the ETG group is directly bonded to a carbon atom of ring A; V is a single bond, C=O, C(R 1 )2, NAr 3 , O, S, Si(R 1 )2, BR 1 , PR 1 , P(=O)R 1 , SO or SO2, where in the case of a single bond, the carbon atoms of rings A and A' are directly bonded to each other by a single bond, preferably a single bond, C(R 1 )2, NAr 3 , O and S, particularly preferably a single bond, C(R 1 )​​​​​​​​​​​​​​​​​​​​​It is even more preferable that if W is not a single bond, then V is a single bond, and if V is not a single bond, then W is a single bond; It is even more very, particularly preferable that V is a single bond when W is O or S, and that W is a single bond when V is O or S; It is even more very, particularly preferable that when W is O, V is a single bond, and when V is O, W is a single bond; m is either 0 or 1; n is either 0 or 1; Here, m=n; Ar 3 is R greater than or equal to 1. 3 One or more R groups may be substituted by other groups. 2 An aromatic ring or ring structure having 6 to 30 ring atoms, each of which may be substituted by a group, where 2 or more R 2 The bases often form a ring together; R 1 These are either the same or different each time they appear: H, D, F, Cl, Br, I, N(R 2 )2, CN, NO2, Si(R 2 )3, B(OR 2 )2, C(=O)R 2 , P(=O)(R 2 )2, S(=O)R 2 , S(=O)2R 2 OSO2R 2 , a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, a linear alkenyl or alkynyl group having 2 to 40 carbon atoms, a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 carbon atoms (each having 1 or more R 2 They may be substituted with groups, and one or more non-adjacent CH2 groups are R 2 C=CR 2 , C≡C, Si(R 2 )2, Ge(R 2 )2, Sn(R 2 )2, C=O, C=S, C=Se, C=NR 2 , P(=O)(R 2), SO, SO2, NR 2 , O, S or CONR 2 It may be replaced by, where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2. ), in each case, one or more R 2 An aromatic or heterocyclic aromatic ring structure having 5 to 60 aromatic ring atoms that may be substituted by groups, 1 or more R 2 An aryloxy, arylalkoxy, or heteroaryloxy group having 5 to 60 aromatic ring atoms which may be substituted by a group, and one or more R 2 A diarylamino group, diheteroarylamino group, or arylheteroarylamino group having 10 to 40 aromatic ring atoms that may be substituted by a group, or a combination of two or more such groups, or a crosslinkable Q group; R 2 These are either the same or different each time they appear: H, D, F, Cl, Br, I, N(R 3 )2, CN, NO2, Si(R 3 )3, B(OR 3 )2, C(=O)R 3 , P(=O)(R 3 )2, S(=O)R 3 , S(=O)2R 3 OSO2R 3 , a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, a linear alkenyl or alkynyl group having 2 to 40 carbon atoms, a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 carbon atoms (each having 1 or more R 3 They may be substituted with groups, and one or more non-adjacent CH2 groups are R 3 C=CR 3 , C≡C, Si(R 3 )2, Ge(R 3 )2, Sn(R 3 )2, C=O, C=S, C=Se, C=NR 3 , P(=O)(R 3 ), SO, SO2, NR 3 , O, S or CONR 3It may be replaced by, where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2. ), in each case, one or more R 3 An aromatic or heterocyclic aromatic ring structure having 5 to 60 aromatic ring atoms that may be substituted by groups, 1 or more R 3 An aryloxy, arylalkoxy, or heteroaryloxy group having 5 to 60 aromatic ring atoms which may be substituted by a group, and one or more R 3 A diarylamino group, diheteroarylamino group, or arylheteroarylamino group, or a combination of two or more such groups, having 10 to 40 aromatic ring atoms that may be substituted by a group; and simultaneously, two or more adjacent R 2 The groups may together form monocyclic or polycyclic aliphatic or aromatic ring structures; R 3 Each occurrence is either identical or different, and is an aliphatic, aromatic and / or heterocyclic aromatic hydrocarbyl group having H, D, F, and 1 to 20 carbon atoms, where 1 or more hydrogen atoms may be replaced by F, and at the same time, 2 or more R 3 The substituents may together form monocyclic or polycyclic aliphatic or aromatic ring structures; p is an integer between 1 and 7, preferably 1 and 4, very preferably 1 and 3, especially preferably 1 and 2, very especially preferably exactly 2, and especially preferably exactly 1; R 4 Each occurrence is either the same or different, and R is 1 or greater. 2 An aromatic ring or ring structure having 6 to 60 aromatic ring atoms that may be substituted by groups, 1 or more R 2 An arylamino group having 10 to 40 aromatic ring atoms that may be substituted by a group, or a combination of two or more of these; in this case, two or more adjacent R groups 4 The groups may together form monocyclic or polycyclic aliphatic or aromatic ring structures.

[0020] Therefore, for example, for a compound of general formula (1), when m=n=1 and V=W=single bond, the general formula is as follows:

[0021] [ka]

[0022] Furthermore, for example, for a compound of general formula (1), if m=n=1, V=O, and W=single bond, the general formula is as follows:

[0023] [ka]

[0024] Furthermore, for example, for a compound of general formula (1), when m=n=0, the general formula is as follows:

[0025] [ka]

[0026] In one preferred embodiment, the compound is selected from the compounds of general formula (2),

[0027] [ka]

[0028] The following additional symbols are used in the formula: X is either the same or different each time it appears, and is either N or CR. 1 and; Q is either the same or different each time it appears, and X = X, S, O, or NR 1 Preferably, X=X, S and O, very preferably, X=X and S, and most preferably, X=X.

[0029] The highly preferred compounds are, therefore, those of general formula (3) to (11),

[0030] [ka]

[0031] [ka]

[0032] [ka]

[0033] Compounds of general formulas (3) to (8) are very particularly preferred, and compound of general formula (4) is especially preferred.

[0034] In equations (1) to (9), X is CR 1 It is even more particularly very preferable when this is the case.

[0035] In one preferred embodiment, the present invention relates to a compound of formula (4), preferably in which X is CR. 1 The compound of formula (4) is such that m is 1, and very preferably X is CR 1 With respect to the compound of formula (4) where m is 1 and V is O, the above definitions and preferred embodiments apply to other symbols and subscripts.

[0036] In one more preferred embodiment, the present invention provides that X is CR 1 Therefore, m=1, and V is N-Ar 3 The compound is of formula (4), where the above definition and preferred embodiments apply to other symbols and subscripts.

[0037] In one more preferred embodiment, the present invention relates to a compound of general formula (12),

[0038] [ka]

[0039] In the formula, V is O or S, where the defined and preferred embodiments apply to the symbols and subscripts used. It is very preferable that V in the compound of the general formula (12) is O.

[0040] In a further preferred embodiment, the present invention relates to a compound of the general formula (13),

[0041]

Chemical formula

[0042] In the formula, V is O or S, where the defined and preferred embodiments apply to the symbols and subscripts used, and here, the aromatic rings A and A' each have no more than one R 1 substituent, that is, s is 0 or 1, t is 0 or 1, where s + t may be 0, 1 or 2. It is very preferable that V in the compound of the formula (13) is O. It is even more preferable that s + t = 0.

[0043] In a preferred embodiment of the present invention, the two R 4 groups of the tertiary amine do not form a ring with each other.

[0044] R 4 If the R 4 group does not form a ring, R 2 is preferably the same or different each time it appears, and in each case is an aromatic ring structure having 6 to 60 aromatic ring atoms optionally substituted by one or more R 2 groups, an arylamino group having 10 to 40 aromatic ring atoms optionally substituted by one or more R

[0045] R 4 groups, or a combination of two or more of these groups. 4 If the R 2 group does not form a ring, R

[0046] R 4 If the group does not form a ring, R 4 is most preferably phenyl, biphenyl, terphenyl, quaterphenyl, carbazole, dibenzofuranyl, particularly preferably phenyl, biphenyl, terphenyl, quaterphenyl, where each group may be substituted by one or more R 2 groups, but is most preferably unsubstituted.

[0047] In a further preferred embodiment of the present invention, the tertiary amine in the compound of general formula (1) is a part of a hetero ring structure which may be aromatic or non - aromatic, where the two R 4 groups form one or more rings, where this means that a nitrogen atom is a constituent of the ring atoms.

[0048] The present invention also relates to a compound of general formula (14), the symbols used are defined as specified herein, and the preferred embodiments otherwise specified in the present invention for the symbols constitute preferred embodiments for the compound of formula (14). X' is N and C(R 2 )2, where not more than four X' are N, preferably not more than two X' are N, very preferably not more than one X' is N, and most preferably all X' are C(R 2 )2.

[0049]

Chemical formula

[0050] A more preferred compound is of general formula (15),

[0051]

Chemical formula

[0052] In the formula, x and y are integers from 0 to 4. The case x+y=0, 1, 2, 3, or 4 is preferred, the case x+y=0, 1, 2, or 3 is very preferred, the case x+y=0, 1, or 2 is particularly preferred, and the case x+y=0 is particularly preferred.

[0053] Another very preferred embodiment is a compound of general formula (16), where B is one or more identical or different R 3 This is an aromatic or heterocyclic aromatic ring structure having 5 to 60 aromatic ring atoms that may be substituted by groups. Here, B forms a fused ring structure with an adjacent carbazole and also with an adjacent indole, where the ring may be assumed to have any possible orientation.

[0054] [ka]

[0055] Here, B is two identical or different R 3 It is particularly preferable that the phenyl ring is substituted with a group. Therefore, the carbazole, indole, and phenyl ring form indrocarbazole.

[0056] An additionally very preferred compound is one with general formula (17), where B is one or more identical or different R 3 This is an aromatic or heterocyclic aromatic ring structure having 5 to 60 aromatic ring atoms that may be substituted by groups. Here, B forms a fused ring structure with an adjacent carbazole and also with an adjacent indane, where the ring may be assumed to have any possible orientation.

[0057] [ka]

[0058] Here, B is two identical or different R 3It is particularly preferable that the phenyl ring is substituted with a group. Therefore, the carbazole, indane, and phenyl ring form indenocarbazole.

[0059] A particularly preferred compound is one with general formula (18).

[0060] [ka]

[0061] Z is preferably a single bond or a divalent aromatic or heterocyclic aromatic ring or ring structure having 5 to 60 ring atoms, preferably an aromatic ring or ring structure having 6 to 60 ring atoms, preferably the ring or ring structure does not bridge to the ring structure containing A and A' or to ETG, preferably Z is a pyridylene, pyrimidylene, phenylene, biphenylene or fluorene, spiro, terphenylene, thiophene or furan group, preferably a phenylene, biphenylene or terphenylene group, and very preferably a phenylene group.

[0062] The expression that two or more groups may form a ring together should be understood in the context of this application to mean, in particular, that two groups are chemically bonded to each other. This is illustrated by the following scheme.

[0063] [ka]

[0064] However, the expression mentioned above should be understood to mean that, when one of the two groups is hydrogen, the second group bonds at the same position as the hydrogen atom to form a ring. This is illustrated by the following scheme.

[0065] [ka]

[0066] A condensed aryl group is understood to mean an aryl group containing two or more aromatic rings fused together, meaning they share one or more aromatic ends. The corresponding definition applies to heteroaryl groups. Examples of condensed aryl groups, regardless of the number of ring atoms, are naphthyl, anthracenyl, pyrenyl, phenantrenyl, and perilenyl. Examples of condensed heteroaryl groups are quinolinyl, indolyl, carbazolyl, and acridinyl.

[0067] The general definition of a chemical group in the context of this application is as follows:

[0068] In the context of this invention, an aryl group contains 6 to 60 aromatic ring atoms, and a heteroaryl group contains 5 to 60 aromatic ring atoms, at least one of which is a heteroatom. The heteroatom is preferably selected from N, O, and S. This is the basic definition. This is applicable where other descriptions are made in the description of this invention, for example, regarding the number of aromatic ring atoms or heteroatoms.

[0069] The aryl group or heteroaryl group is understood to mean any of the following: a simple aromatic ring, i.e., benzene, or a simple heterocyclic aromatic ring, such as pyridine, pyrimidine, thiophene, etc., or a condensed (cyclized) aromatic or heterocyclic aromatic polycyclic ring, such as naphthalene, phenanthrene, quinoline, or carbazole, etc. In the context of this invention, a condensed (cyclized) aromatic or heterocyclic aromatic polycyclic ring consists of two or more simple aromatic or heterocyclic aromatic rings fused together.

[0070] In the context of the present invention, an electron-deficient heteroaryl group is defined as a five-membered heteroaryl group containing at least two heteroatoms, such as imidazole, oxazole, oxadiazole, etc., or a six-membered heteroaryl group containing at least one heteroatom, such as pyridine, pyrimidine, pyrazine, triazine, etc. Further six-membered aryl or six-membered heteroaryl groups can condense to these groups, for example, benzimidazole, quinoline, or phenanceroline.

[0071] The aryl or heteroaryl groups may be substituted with the groups mentioned above, and may be linked to aromatic or heterocyclic aromatic systems via any desired position, in particular benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzo Nzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenantholidine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthoidazole, pyridoimidazole, pyrazineimidazole, quinoxalineimidazole, oxazole, Benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, pyrazine, phenazine, naphthyrizine, azacarbazole, benzocarbolin, phenanthroxazole, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadi This is understood to mean groups derived from azole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indidine, and benzothiadiazole.

[0072] In this invention, the aryloxy group is understood to mean an aryl group bonded via an oxygen atom, as defined above. A similar definition applies to heteroaryloxy groups.

[0073] In the context of this invention, an aromatic ring structure contains 6 to 60 carbon atoms in the ring structure. In the context of this invention, a heterocyclic aromatic ring structure contains 5 to 60 aromatic ring atoms, at least one of which is a heteroatom. The heteroatom is preferably selected from N, O and / or S. In the context of this invention, an aromatic or heterocyclic aromatic ring structure is not necessarily a structure that contains only aryl or heteroaryl groups, and two or more aryl or heteroaryl groups are non-aromatic units (preferably less than 10% of atoms other than H), for example, sp 3 Hybrid carbon, silicon, nitrogen or oxygen atoms, sp 2 It is understood that this refers to structures that may be linked by hybridized carbon or nitrogen atoms, sp hybridized carbon atoms, etc. Therefore, structures such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamines, diaryl ethers, and stilbenes are similarly considered aromatic ring structures in the context of the present invention, since they are structures in which two or more aryl groups are linked, for example, by linear or cyclic alkyl, alkenyl or alkynyl groups, or by silyl groups. Furthermore, structures in which two or more aryl or heteroaryl groups, such as biphenyl, terphenyl or diphenyltriazine, are linked to each other via single bonds are also considered aromatic or heterocyclic aromatic ring structures in the context of the present invention.

[0074] Aromatic or heterocyclic aromatic ring structures having 5 to 60 aromatic ring atoms may, in each case, be substituted with the above-mentioned groups and may be linked to the aromatic or heterocyclic aromatic structure at any desired position, in particular benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzphenanthrene, pyrene, chrysene, perylene, fluorantene, naphthalene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene, quaterphenyl, fluorene, spirobifluorene, dihydrofluorene Drophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, torxene, isotorthorxene, spirotorxene, spiroisotorxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, indolocarbazole, indenocarbazole, pyridine, quinoline, isoquinoline, acridine, phenanthoridine, benzo-5,6-quinoli N, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazineimidazole, quinoxalineimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, Benzopyrimidine, quinoxaline, 1,5-diazaanthracene, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorbin, naphthyridine, azacarbazole, benzocarbolin, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,This is understood to mean groups derived from 3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purines, pteridines, indidines, and benzothiadiazole or combinations thereof.

[0075] In the context of the present invention, a linear alkyl group having 1 to 40 carbon atoms, a branched or cyclic alkyl group having 3 to 40 carbon atoms, or an alkenyl or alkynyl group having 2 to 40 carbon atoms is, herein, in addition, individual hydrogen atoms or CH2 groups may be substituted with the groups mentioned above under the definition of the group, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, neo-butyl It is understood to mean thyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethinyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, or octinyl group.The alkoxy or thioalkyl group having 1 to 40 carbon atoms is preferably methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy, 2,2,2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, n- It is understood to mean pentylthio, s-pentylthio, n-hexylthio, cyclohexylthio, n-heptithiol, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, etenylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, cyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthio, cyclooctenylthio, ethinylthio, propynylthio, butynylthio, pentynylthio, hexynylthio, heptynylthio, or octinylthio.

[0076] The ETG group preferably has 1 or more R groups. 1 It is an electron-deficient heterocyclic aromatic group that may be substituted with a group. More preferably, it is a heterocyclic aromatic group having six aromatic ring atoms, at least one, preferably two, and very preferably at least three of which are nitrogen atoms, or at least two heteroatoms, preferably at least one of which is R 1 A heterocyclic aromatic group having an aromatic ring atom having five aromatic ring atoms, each of which is a nitrogen atom that may be substituted by a further aryl or heteroaryl group may be fused to each of these groups.

[0077] Preferred electron-deficient heterocyclic aromatic groups are selected from the following groups:

[0078] [ka]

[0079] In the formula, the dashed lines indicate attached positions, R 1 It is as defined above, and Q' is either the same or different each time it appears, CR 1 or N are; and Q is NR 1 , O or S; Here, at least one Q' is N and / or at least one Q'' is NR 1 That is the case.

[0080] Preferred examples of electron-deficient heterocyclic aromatic groups are pyridine, pyrazine, pyrimidine, pyridazine, 1,2,4-triazine, 1,3,5-triazine, quinoline, isoquinoline, quinoxaline, pyrazole, imidazole, benzimidazole, thiazole, benzothiazole, oxazole, or benzoxazole, respectively, R 1 It may be substituted with. More preferably, the electron transport group is one or more R 1 These are pyridine, pyrazine, pyrimidine, pyridazine, and 1,3,5-triazine substituted with the group.

[0081] The following groups are highly preferred electron-deficient heterocyclic aromatic groups.

[0082] [ka]

[0083] R during ETG 1 The substituents are preferably H and, in each case, one or more R 2 The groups are selected from aromatic or heterocyclic aromatic ring structures having 5 to 60 aromatic ring atoms that may be substituted with the group, and more preferably the groups are those of formula (E-11), (E-17), and (E-18), with the most preferred group being formula (E-11).

[0084] A particularly favorable example of an ETG is one or more independent R 2 The following groups may be substituted by the group, where the dashed bond is Ar 1 and Ar 2 This indicates the bond position to the group.

[0085] [ka]

[0086] [ka]

[0087] The electron transport group preferably has a LUMO (lowest unoccupied molecular orbital) of less than -1.3 eV, very preferably less than -2.5 eV, and most preferably less than -2.7 eV.

[0088] The molecular orbitals of a material, particularly the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO), their energy levels, and the energies of the lowest triplet state T1 and the lowest excited singlet state S1, are determined by quantum chemical calculations. For calculations of non-metallic organic materials, geometric optimization is first performed using the "ground state / quasi-experimental / default spin / AM1 / charge 0 / singlet spin" method. Subsequently, energy calculations are performed based on the geometric optimization. This is done using the "TD-SCF / DFT / default spin / B3PW91" method with the "6-31G(d)" base set (charge 0, singlet spin). For metal-containing compounds, the geometry is optimized via the "ground state / Hartree-Fock / default spin / LanL2MB / charge 0 / singlet spin" method. Energy calculations are performed in the same way as for organic materials as described above, except that the “LanL2DZ” base set is used for metal atoms and the “6-31G(d)” base set is used for ligands. The HOMO energy level HEh or LUMO energy level LEh is obtained from energy calculations in Hartree units. This is used to determine the energy levels in electron volts of the HOMO and LUMO, calibrated with reference to cyclic voltammetry measurements, as follows: HOMO(eV)=((HEh*27.212)-0.9899) / 1.1206 LUMO(eV)=((LEh*27.212)-2.0041) / 1.385 These values ​​should be considered as the HOMO and LUMO energy levels of the material in the context of this application.

[0089] The lowest triplet state T1 is defined as the energy of the lowest energy triplet state, which is clear from the above quantum chemical calculations.

[0090] The lowest excited singlet state S1 is defined as the energy of the lowest excited singlet state, which is clear from the above quantum chemical calculations.

[0091] The methods described here are independent of the software packages used and will always yield the same results. Examples of programs commonly used for this purpose include "Gaussian09W (Gaussian Inc.) and Q-Chem 4.1 (Q-Chem, Inc.)".

[0092] More preferably, the electron transport group has an electron mobility μ of 10 -6 cm 2 / (Vs) or more, very preferably 10 -5 cm 2 / (Vs) or more, most preferably 10 -4 cm 2 It is characterized by being greater than or equal to / (Vs).

[0093] In the compound of formula (1), the LUMO is preferably localized to the electron transport group. It is very preferable that the LUMO is localized to the electron transport group by 80% or more, and even more preferably that the LUMO is not localized at all on the carbazole group. It is particularly preferable that the absolute grades of the HOMO and LUMO of the compound of the present invention do not overlap at all. Those skilled in the art will have no difficulty in measuring the overlap of absolute grades of the orbitals. For this purpose, the calculation method specified herein is used, and an orbital with a 90% probability density is assumed.

[0094] Ar 3 It is very preferably one or more R 3 One or more R groups may be substituted with the R group. 2 An aromatic ring or ring structure having 5 to 30 ring atoms, each of which may be substituted with an Ar group, and more preferably, Ar 3 It has not been replaced.

[0095] The most particularly preferred aromatic groups are phenyl, biphenyl, terphenyl, and quaterphenyl.

[0096] In one preferred embodiment, the present invention relates to compounds of the above general formula, and excludes the following compounds.

[0097] [ka]

[0098] The compounds of the present invention may be prepared according to schemes 1 to 5. The corresponding monofunctionalized ortho compounds can be prepared by Buchwald coupling with an arylamine or carbazole. The corresponding target compounds can be commercially produced by monolithiation, reaction with BBr3, and subsequent Suzuki coupling (Scheme 1).

[0099] [ka]

[0100] Scheme 2 Applicable to dibenzofurans, Scheme 1 is applied as follows: The corresponding monofunctionalized orthodibenzofuran can be prepared by Buchwald coupling with an arylamine (modified 1) or a carbazole (modified 2). The corresponding target compound can be commercially produced by monolithiation, reaction with BBr3, and subsequent Suzuki coupling.

[0101] [ka]

[0102] [ka]

[0103] In the formula, R is in an undefined position. 1 and R 2 The base is as defined above and may appear repeatedly on each ring.

[0104] Scheme 3 A further means of producing the compound of the present invention involves reacting a dihalide with one equivalent of amine (Buchwald), followed by a reaction with boronic acid (Suzuki).

[0105] [ka]

[0106] In the formula, Y is a halide, in particular I or Br.

[0107] Scheme 4 A diagram illustrating the application of Scheme 3 to 9H-xanthene is shown below.

[0108] [ka]

[0109] The reaction scheme can be applied to both amines and carbazoles. Those skilled in the art will have no difficulty applying the specific reaction to further structures, not just dibenzofuran or 9H-xanthenes.

[0110] Many halides, dihalides, and boronic acids are commercially available. Furthermore, they can be manufactured very easily using methods that are very familiar to chemists.

[0111] Scheme 5 demonstrates this with an example using dibenzofuran.

[0112] Scheme 5

[0113] [ka]

[0114] Here, halides other than iodine, in particular brominated halides, may also be produced in this manner.

[0115] The following overview includes examples of compounds that can be prepared by one of the processes described here.

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[0117]

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[0118]

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[0122]

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[0134] The present invention further provides the use of the compound of formula (1) in an electronic device, preferably in an electron transport layer and / or light-emitting layer.

[0135] The electronic elements of the present invention are preferably selected from the group consisting of organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (OLETs), organic solar cells (O-SCs), organic optical inspection elements, organic photoreceptors, organic field-quenched elements (OFQDs), organic light-emitting electrochemical cells (OLECs, LECs, LEECs), organic laser diodes (O-lasers), and organic light-emitting diodes (OLEDs). Particularly preferred are organic electroluminescent elements, very particularly preferred are OLECs and OLEDs, and especially preferred are OLEDs.

[0136] The organic layer containing the compound of formula (1) preferably includes a layer having electron transport function. Preferably, it is an electron injection layer, an electron transport layer, a hole blocking layer, or an emissive layer.

[0137] In one particularly preferred embodiment, the compound of formula (1) is used in the light-emitting layer, in particular as a matrix material.

[0138] The hole transport layer according to this application is a layer having a hole transport function between the anode and the light-emitting layer.

[0139] The electron transport layer according to this application is a layer having an electron transport function between the cathode and the light-emitting layer.

[0140] In the context of this application, hole injection layers and hole blocking layers are understood to be special embodiments of hole transport layers. In the case of multiple hole transport layers between the anode and the light-emitting layer, the hole injection layer is either a hole transport layer directly adjacent to the anode or separated from it only by a single covering of the anode. In the case of multiple hole transport layers between the anode and the light-emitting layer, the electron blocking layer is a hole transport layer directly adjacent to the light-emitting layer on the anode side.

[0141] As already mentioned above, in one preferred embodiment, the compound of formula (1) is used as a matrix material in the light-emitting layer of an organic electronic device, particularly an organic electroluminescent device, such as an OLED or OLEC. In this case, the matrix material of formula (1) is present in the electronic device in combination with one or more dopants, preferably phosphorescent dopants.

[0142] The term "phosphor dopant" typically refers to compounds whose luminescence arises from spin-forbidden transitions, such as from an excited triplet state or a state with a relatively high spin quantum number, such as a quintet state.

[0143] A suitable phosphorescent dopant is a compound that, in particular, emits light in the visible range upon appropriate excitation, and also contains at least one atom having an atomic number greater than 20, preferably between 38 and 84, and more preferably between 56 and 80. The phosphorescent dopant used is preferably a compound containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium, and in particular a compound containing iridium, platinum, or copper.

[0144] In the context of this application, all luminescent iridium, platinum, or copper complexes are considered phosphorescent compounds. Examples of phosphorescent dopants are shown in the following sections.

[0145] In a system containing a matrix material and a dopant, the dopant is understood to mean the component that makes up a smaller proportion of the mixture. Correspondingly, in a system containing a matrix material and a dopant, the matrix material is understood to mean the component that makes up a larger proportion of the mixture.

[0146] In this case, the proportion of matrix material in the light-emitting layer is 50.0 to 99.9 volume%, preferably 80.0 to 99.5 volume%, and more preferably 92.0 to 99.5 volume%, relative to the fluorescent light-emitting layer, and 85.0 to 97.0 volume%, relative to the phosphorescent light-emitting layer.

[0147] Accordingly, the proportion of the dopant is 0.1 to 50.0 volume%, preferably 0.5 to 20.0 volume%, and more preferably 0.5 to 8.0 volume%, relative to the fluorescent luminescence layer, and 3.0 to 15.0 volume%, relative to the phosphorescent luminescence layer.

[0148] The light-emitting layer of an organic electroluminescent element may also contain multiple matrix materials (mixed matrix systems) and / or multiple dopants. In this case as well, the dopants are generally materials present in a smaller proportion in the system, and the matrix materials are materials present in a larger proportion. However, in individual cases, the proportion of a single matrix material in the system may be less than the proportion of a single dopant.

[0149] In a more preferred embodiment of the present invention, the compound of formula (1) is used as a component of a mixed matrix system. The mixed matrix system preferably comprises two or three different matrix materials, more preferably two different matrix materials. Preferably, in this case, one of the two materials is a material having hole transport properties and the other is a material having electron transport properties. However, the desired electron transport and hole transport properties of the mixed matrix components may be mainly or completely coupled in a single mixed matrix component, in which case further mixed matrix components perform other functions. Here, the two different matrix materials may be present 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. Preferably, the mixed matrix system is used in phosphorescent organic electroluminescent elements. One more precise source of information regarding mixed matrix systems is application WO 2010 / 108579.

[0150] Particularly suitable matrix materials that can be used as matrix components in combination with the compounds of the present invention are selected from the preferred matrix materials for phosphorescent dopants or preferred matrix materials for fluorescent dopants shown below, depending on which type of dopant is used in the mixed matrix system.

[0151] Therefore, the present invention also relates to a composition comprising at least one compound of formula (1) and at least one further matrix material.

[0152] The present invention also relates to compositions comprising at least one compound of formula (1) and at least one broad-bandgap material, where the broad-bandgap material is understood to mean a material in the sense of the disclosure of US 7,294,849. These systems exhibit particularly favorable performance data in electroluminescent devices.

[0153] The present invention further relates to a composition comprising at least one compound of formula (1) and at least one further organic semiconductor material selected from the group consisting of fluorescent emitters, phosphorescent emitters, host materials, matrix materials, electron transport materials, electron injection materials, hole conduction materials, hole injection materials, electron blocking materials and hole blocking materials.

[0154] Preferred phosphorescent dopants for use in mixed matrix systems are the preferred phosphorescent dopants specified below.

[0155] Examples of phosphorescent dopants are revealed in applications WO 2000 / 70655, WO 2001 / 41512, WO 2002 / 02714, WO 2002 / 15645, EP 1191613, EP 1191612, EP 1191614, WO 2005 / 033244, WO 2005 / 019373 and US2005 / 0258742. Generally, all phosphorescent complexes used in accordance with the prior art for phosphorescent OLEDs and known to those skilled in the art in the field of organic electroluminescent devices are suitable.

[0156] A clear example of a phosphorescent dopant is shown in the table below.

[0157] [ka]

[0158] [ka]

[0159] [ka]

[0160] [ka]

[0161] [ka]

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[0165] [ka]

[0166] [ka]

[0167] Preferred fluorescent dopants are selected from the class of arylamines. In the context of the present invention, arylamine or aromatic amine is understood to mean a compound containing three substituted or unsubstituted aromatic or heterocyclic aromatic ring structures directly bonded to nitrogen. At least one of these aromatic or heterocyclic aromatic ring structures is preferably a fused ring structure and more preferably has at least 14 aromatic ring atoms. These preferred examples are aromatic anthraceneamines, aromatic anthracenediamines, aromatic pyreneamines, aromatic pyrenediamines, aromatic chrysenamines, or aromatic chrysendiamines. Aromatic anthraceneamine is understood to mean a compound in which one diarylamino group is directly bonded to an anthracene group, preferably at the 9-position. Aromatic anthracenediamine is understood to mean a compound in which two diarylamino groups are directly bonded to an anthracene group, preferably at the 9- and 10-positions. Aromatic pyreneamines, pyrenediamines, chrysenamines, and chrysendiamines are similarly defined, where the diarylamino group is preferably bonded to pyrene at the 1- or 1.6-position. More preferred dopants are, for example, indenofluorenamine or indenofluororangeamine according to WO 2006 / 10849 or WO 2006 / 122630, for example, benzoindenofluorenamine or benzoindenofluororangeamine according to WO 2008 / 006449, and for example, dibenzoindenofluorenamine or dibenzoindenofluororangeamine according to WO 2007 / 140847, and indenofluorene derivatives containing a condensed aryl group as disclosed in WO 2010 / 012328.

[0168] Preferably, useful matrix materials for the fluorescent dopant are materials from various classes of substances, similar to the compounds of formula (1). Preferred matrix materials are oligoarylenes (e.g., 2,2’,7,7’-tetraphenylspirobifluorene or dinaphthylanthracene according to EP 676461), in particular oligoarylenes containing condensed aromatic groups, oligoarylenevinylenes (e.g., DPVBi or spiro-DPVBi according to EP 676461), polypodal metal complexes (e.g., according to WO 2004 / 081017), hole-conducting compounds (e.g., according to WO 2004 / 058911), electron-conducting compounds, in particular ketones, phosphine oxides, sulfoxides, etc. (e.g., according to WO 2005 / 084081 and WO 2005 / 084082), atropisomers (e.g., according to WO 2006 / 048268), boronic acid derivatives (e.g., according to WO 2006 / 177052) or benzanthracenes (e.g., according to WO2008 / 1452), which are selected from the class of compounds. Particularly preferred matrix materials are selected from the class of oligoarylenes containing naphthalene, anthracene, benzanthracene and / or pyrene or atropisomers of these compounds, oligoarylenevinylenes, ketones, phosphine oxides and sulfoxides. Very particularly preferred matrix materials are selected from the class of oligoarylenes containing anthracene, benzanthracene, benzophenanthrene and / or pyrene or atropisomers of these compounds. Oligoarylene in the context of the present invention is understood to mean a compound in which at least three aryl or arylene groups are bonded to each other.

[0169] Preferred matrix materials for phosphorescent dopants are aromatic amines, particularly triarylamines, carbazole derivatives (CBP, N,N-biscarbazolylbiphenyl) according to US2005 / 0069729, or compounds according to WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 288381, EP1205527 or WO2008 / 086851, e.g., crosslinked carbazole derivatives according to WO 2011 / 088877 and WO 2011 / 128017, e.g., indenocarbazole derivatives according to WO2010 / 136109 and WO2011 / 000455, e.g., EP 1617710, EP 1617711, EP 1731584, JP Azacarbazole derivatives according to 2005 / 347160, e.g., indolocarbazole derivatives according to WO 2007 / 063754 or WO 2008 / 056746, e.g., ketones according to WO 2004 / 093207 or WO 2010 / 006680, e.g., phosphine oxides, sulfoxides and sulfones, oligoarylenes according to WO 2005 / 003253, e.g., bipolar matrix materials according to WO 2007 / 137725, e.g., WO Silanes according to 2005 / 111172, for example; azabolol or boronic acid esters according to WO2006 / 117052, for example; triazine derivatives according to WO2010 / 15306, WO2007 / 063754 or WO2008 / 056746, for example; zinc complexes, aluminum complexes according to EP652273 or WO2009 / 062578, for example; BAlq, for example; diazasilol derivatives or tetraazalol derivatives according to WO2010 / 054729, for example; diazaphosphole derivatives and aluminum complexes according to WO2010 / 054730, for example; BAlq.

[0170] Apart from the layer containing the cathode, anode and the compound of formula (1), the electronic device may further include additional layers. These may include, for example, in each case, one or more hole injection layers, hole transport layers, hole blocking layers, light emitting layers, electron transport layers, electron injection layers, electron blocking layers, exciton blocking layers, intermediate layers, charge generation layers (IDMC 2003, Taiwan; Session 21 OLED (5), T. Matsumoto, T. Nakada, J. Endo, K. Mori, N. Kawamura, A. Yokoi, J. Kido, Multiphoton Organic EL Device Having Charge Generation Layer) and / or may include organic or inorganic p / n junctions. However, it must be pointed out that each of these layers does not necessarily have to be present.

[0171] The layer arrangement in an organic electroluminescent device is preferably as follows: anode - hole injection layer - hole transport layer - light emitting layer - electron transport layer - electron injection layer - cathode.

[0172] Here, it is necessary to point out again that not all of the above layers necessarily have to be present and / or additional layers may additionally be present.

[0173] The organic electroluminescent element of the present invention may include two or more light-emitting layers. In this case, these light-emitting layers more preferably have several maximum emission wavelengths in total between 380 nm and 750 nm, resulting in white light emission as a whole. In other words, various light-emitting compounds that emit fluorescence or phosphorescence and can emit blue, yellow, orange, or red light can be used as light-emitting layers. Particularly preferred is a three-layer structure, that is, a structure having three light-emitting layers, the three layers exhibiting blue, green, and orange or red light emission (for the basic structure, see, for example, WO 2005 / 011013). It should be noted that for the generation of white light, individually used emitter compounds that emit light over a broad wavelength range may be more suitable than multiple emitter compounds that emit color light.

[0174] Suitable charge transport materials that can be used in the hole injection or hole transport layer, or in the electron block layer or electron transport layer of the organic electroluminescent element of the present invention are, for example, the compounds disclosed in Y. Shirota et al., Chem. Rev. 2007, 107(4), 953-1010 or other materials used in these layers by prior art.

[0175] The materials used for the electron transport layer are all materials used in the prior art as electron transport materials in the electron transport layer. Particularly suitable are aluminum complexes, e.g., Alq3; zirconium complexes, e.g., Zrq4; benzimidazole derivatives; triazine derivatives; pyrimidine derivatives; pyridine derivatives; pyrazine derivatives; quinoxaline derivatives; quinoline derivatives; oxadiazole derivatives; aromatic ketones; lactams; boranes; diazaphosphole derivatives; and phosphine oxide derivatives. Furthermore, suitable materials are derivatives of the compounds mentioned above, as disclosed in JP2000 / 053957, WO2003 / 060956, WO 2004 / 028217, WO 2004 / 080975, and WO 2010 / 072300.

[0176] Preferred hole transport materials that can be used in hole transport, hole implantation, or in electron block layers include indenofluorenamine derivatives (e.g., according to WO 2006 / 122630 or WO2006 / 100896), amine derivatives disclosed in EP1661888, hexaazatriphenylene derivatives (e.g., according to WO 01 / 049806), amine derivatives having condensed aromatic systems (e.g., according to US5,061,569), amine derivatives disclosed in WO95 / 09147, monobenzoindenofluorenamine (e.g., according to WO2008 / 006449), dibenzoindenofluorenamine (e.g., according to WO These include spirobifluorenamine (e.g., WO2012 / 034627 or unpublished EP12000929.5), fluorenamine (e.g., unpublished applications EP12005369.9, EP12005370.7 and EP12005371.5), spirodibenzopyranamine (e.g., published application EP 11009127.9), and dihydroacridine derivatives (e.g., published application EP 11007067.9).

[0177] Preferred cathodes for electronic devices include metals with low work functions, metal alloys containing various metals, or multilayer structures, such as alkaline earth metals, alkali metals, main group metals, or lanthanide metals (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Additionally suitable are alloys containing alkali metals or alkaline earth metals with silver, such as alloys containing magnesium and silver. In the case of multilayer structures, in addition to the aforementioned metals, further metals with relatively high work functions, such as Ag or Al, may also be used, in which case combinations of metals such as Ca / Ag, Mg / Ag, or Ba / Ag are commonly used. It may also be preferable to insert a thin interlayer of a material with a high dielectric constant between the metal cathode and the organic semiconductor. Examples of materials useful for this purpose include alkali metal fluorides or alkaline earth metal fluorides as well as their corresponding oxides or carbonates (e.g., LiF, Li2O, BaF2, MgO, NaF, CsF, Cs2CO3, etc.). Furthermore, lithium quinolinate (LiQ) can be used for this purpose. The thickness of this layer is preferably 0.5 to 5 nm.

[0178] A preferred anode is a material with a high work function. Preferably, the anode has a work function higher than 4.5 eV relative to vacuum. Suitable for this purpose are, firstly, metals with high reduction potentials, such as Ag, Pt, or Au; secondly, metal / metal oxide electrodes (e.g., Al / Ni / NiO) x Al / PtO x) may also be preferable. For some applications, at least one electrode must be transparent or partially transparent to allow either irradiation (organic solar cells) or emission (OLED, O-LASER) of an organic material. Here, preferred anode materials are conductive mixed metal oxides. Particularly preferred are indium tin oxide (ITO) or indium zinc oxide (IZO). Even more preferred are conductive doped organic materials, in particular conductive doped polymers. Furthermore, 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.

[0179] During manufacturing, the electronic elements are appropriately structured (depending on the application), provided with contacts, and finally sealed, as the lifespan of the elements according to the present invention is shortened in the presence of water and / or air.

[0180] In one preferred embodiment, the electronic element of the present invention is characterized in that one or more layers are applied by a sublimation process. In this case, the material is 10 -5 Less than mbar, preferably 10 -6 Vacuum vapor deposition occurs in a vacuum sublimation unit at an initial pressure of less than mbar. In this case, however, the initial pressure can be even lower, for example, 10 -7 It is also possible to do so with less than mbar.

[0181] Similarly, a preferred organic electroluminescent element is characterized in that one or more layers are applied by an OVPD (organic vapor deposition) process or carrier gas sublimation. In this case, the material is 10 -5 It is applied at a pressure of mbar to 1 bar. A special case of this process is the OVJP (Organic Vapor Jet Printing) process, where the material is applied directly by a nozzle and then structured (e.g., MS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).

[0182] An additionally preferred organic electroluminescent element is characterized in that one or more layers are manufactured from a solution, for example by spin coating, or by any desired printing process such as screen printing, flexographic printing, nozzle printing or offset printing, more preferably 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 the compound.

[0183] The organic electroluminescent element of the present invention is more preferably manufactured by applying one or more layers from a solution and one or more layers by a sublimation process.

[0184] Therefore, the present invention relates to a method for manufacturing an electronic device, characterized in that at least one organic layer is applied by vapor deposition or from a solution.

[0185] According to the present invention, an electronic element comprising one or more compounds of formula (I) can be used as a light source for illumination applications, as a light source for medical and / or cosmetic applications (e.g., phototherapy), and in particular, in a display device.

[0186] The present invention also relates to a preparation comprising at least one compound of formula (I) or at least one of the above-mentioned compositions and at least one solvent.

[0187] Suitable and preferred solvents include, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, bellator, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene, (-)-phenconne, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinene, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, α-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexano These are cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indan, methyl benzoate, NMP, p-cymene, phenethole, 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, or mixtures of these solvents.

[0188] The device containing the compound of formula (1) can be used in a very versatile manner. For example, an electroluminescent device containing one or more compounds of formula (1) can be used in display devices for televisions, mobile phones, computers, and cameras. Alternatively, the device may also be used for lighting applications. Further, for example, in OLED or OLEC, an electroluminescent device containing at least one compound of formula (1) can be utilized in phototherapy in medicine or cosmetology. Therefore, a number of diseases (psoriasis, atopic dermatitis, inflammation, acne, skin cancer, etc.), or treatments for preventing or reducing skin wrinkles, skin redness, and skin aging can be carried out. Further, a light-emitting device can be utilized to keep beverages, foods or food products fresh, or to sterilize devices (such as medical devices).

[0189] Therefore, the present invention also relates to an electronic device, preferably an organic electroluminescent device, very preferably an OLED or OLEC, most preferably an OLED, containing at least one compound of formula (1) for use in phototherapy in medicine.

[0190] Therefore, the present invention more preferably also relates to an electronic device, preferably an organic electroluminescent device, very preferably an OLED or OLEC, most preferably an OLED, containing at least one compound of formula (1) for use in phototherapy for skin diseases.

[0191] Therefore, the present invention further relates to an electronic device, preferably an organic electroluminescent device, very preferably an OLED or OLEC, most preferably an OLED, containing at least one compound of formula (1) for use in phototherapy for psoriasis, atopic dermatitis, inflammation, acne, and skin cancer.

[0192] The present invention further relates to an electronic device, preferably an organic electroluminescent device, very preferably an OLED or OLEC, most preferably an OLED, comprising at least one compound of formula (1), for cosmetic use, preferably for the treatment of acne, skin aging and cellulite.

[0193] The compounds and organic electroluminescent elements of the present invention differ from the prior art due to the following remarkable advantages that surpass those of the prior art.

[0194] 1. The compounds of the present invention have extremely good stability for use in light-emitting layers and exhibit improved performance that surpasses compounds from the prior art.

[0195] 2. The compounds of the present invention have a relatively low sublimation temperature and high temperature stability, and therefore can sublimate without decomposition or residue. Furthermore, they have high oxidation stability and a high glass transition temperature, which is advantageous for both processing capabilities, for example, from solution or gas phase, and for use in electronic devices.

[0196] 3. When the compounds of the present invention are used in electronic devices, particularly as electron transport or electron injection materials, and further as matrix materials, they result in higher efficiency, lower drive voltage, and longer lifespan.

[0197] It should be noted that variations of the embodiments described in this invention fall within the scope of the present invention. Each feature disclosed in this invention may be replaced by alternative features that serve the same, equivalent, or similar purposes unless explicitly excluded. Therefore, unless otherwise specified, each feature disclosed in this invention should be considered either a general set of examples or an equivalent or similar feature.

[0198] All features of the present invention can be combined with one another, in any case, provided that no feature and / or process mutually excludes each other. This is especially true of the preferred features of the present invention. Similarly, non-essential combination features may be used separately (instead of in combination).

[0199] Many features, in particular, those of preferred embodiments of the present invention, must be considered inventive in themselves and not merely as parts of embodiments of the present invention. Independent protection may be granted for these features, in addition to or as an alternative to the present claimed invention.

[0200] The teachings relating to the technical functions disclosed in this invention can be extracted and combined with other examples.

[0201] The present invention will be described in more detail by the following examples, but will not be limited thereto.

[0202] example: The following synthesis should be carried out in anhydrous solvent under a protective gas atmosphere unless otherwise specified. Solvents and reagents can be purchased, for example, from Sigma-ALDRICH or ABCR. The numbers in square brackets for compounds known from the literature are CAS numbers.

[0203] Example 1 Synthesis of (6-bromodibenzofuran-4-yl)trimethylsilane

[0204] [ka]

[0205] 52 g (159 mmol) of 4,6-dibromodibenzofuran is suspended in 300 mL of THF and 1100 mL of diethyl ether and cooled to -70°C. 78 g (175 mmol) of phenyllithium (1.9 mol / L in dibutyl ether) is slowly added dropwise to this suspension. Then, 20 g (191 mmol) of chlorotrimethylsilane is added dropwise, and the mixture is warmed to room temperature. Water is added to the mixture to remove the organic phase, and the mixture is filtered through silica gel, washed three times with 200 mL of water, and then concentrated to dryness. The residue is recrystallized from toluene. The yield is 49.7 g (121 mmol), which corresponds to 97% of the theoretical value.

[0206] The following compounds can be obtained using a similar method:

[0207] [ka]

[0208] Example 2 Synthesis of (6-bromodibenzofuran-4-yl)trimethylsilane

[0209] [ka]

[0210] A degassed solution of 50 g (156 mmol) of (6-bromodibenzofuran-4-yl)trimethylsilane and 31 g (187 mmol) of carbazole in 600 mL of DMF is saturated with N2 for 1 hour. Then, 3.5 g (15.6 mmol) of 1,3-di(2-pyridyl)-1,3-propanedione is added to this solution, followed by 3 g (15 mmol) of copper, and then 43 g (313 mmol) of solid K2CO3. The reaction mixture is heated under reflux for 1 hour. After cooling to room temperature, 500 mL of water is carefully added. The aqueous phase is washed three times with 50 mL of toluene, dehydrated with MgSO4, and the solvent is removed under reduced pressure. The crude product is then purified by chromatography with heptane / ethyl acetate (20:1) using silica gel. The yield was 38 g (94 mmol), which corresponds to 60% of the theoretical value.

[0211] The following compounds can be obtained using a similar method:

[0212] [ka]

[0213] [ka]

[0214] [ka]

[0215] [ka]

[0216] [ka]

[0217] Example 3 Synthesis of bis(biphenyl-4-yl)dibenzofuran-4-ylamine

[0218] [ka]

[0219] A degassed solution of 43.92 g (176 mmol) of 4-bromodibenzofuran and 47.41 g (148 mmol) of bis(biphenyl-4-yl)amine in 700 mL of toluene is saturated with N2 for 30 minutes. Then, to this solution, first, 2.51 mL (10.3 mmol) of 1 M P(tBu)3 solution in toluene is added, followed by 1.66 g (7.3 mmol) of palladium(II) acetate, and then 21.24 g (222 mmol) of solid NaOtBu. The reaction mixture is heated under reflux for 6 hours. After cooling to room temperature, 500 mL of water is carefully added. The aqueous phase is washed three times with 70 mL of toluene, dehydrated with MgSO4, and the solvent is removed under reduced pressure. The crude product is then purified by chromatography with heptane / ethyl acetate (20:1) using silica gel. The yield was 70.91 g (142.8 mmol), which corresponds to 94% of the theoretical value.

[0220] The following compounds can be obtained using a similar method:

[0221] [ka]

[0222] [ka]

[0223] Example 4 Synthesis of 9-(6-trimethylsilanyldibenzofuran-4-yl)-9H-carbazole

[0224] [ka]

[0225] Suspend 27 g (67 mmol) of 9-dibenzofuran-4-yl-9H-carbazole and 9.3 g (80 mmol) of TMEDA in 700 mL of diethyl ether. Slowly add 32 g of tert-butyllithium (in pentane, 1.7 mol / L) to this suspension.

[0226] The mixture is then cooled to 0°C, 10.9 g (10¹ mmol) of chlorotrimethylsilane is added dropwise, and the mixture is warmed to room temperature. Water is added to the mixture to remove the organic phase, the mixture is filtered through silica gel, washed three times with 200 mL of water, and then concentrated to dryness. The residue is recrystallized from toluene. The yield is 19 g (41 mmol), which corresponds to 60% of the theoretical value.

[0227] The following compounds can be obtained using a similar method:

[0228] [ka]

[0229] [ka]

[0230] Example 5 Synthesis of dibenzofuran-4-yl-9H-carbazole-9-boronic acid

[0231] [ka]

[0232] Under protective gas conditions, 7.8 g (31 mmol) of bromine tribromide was added dropwise to a solution of 10 g (26 mmol) of 9-(6-trimethylsilanyldibenzofuran-4-yl)-9H-carbazole in 100 mL of dichloromethane, and the mixture was stirred at room temperature for 10 hours. Then, small amounts of water were gradually added to the mixture, the precipitated residue was filtered, and washed with heptane. The yield was 9.3 g (25 mmol), corresponding to 94% of the theoretical value.

[0233] The following compounds can be obtained using a similar method:

[0234] [ka]

[0235] [ka]

[0236] [ka]

[0237] [ka]

[0238] [ka]

[0239] [ka]

[0240] [ka]

[0241] Example 6 Synthesis of 9-{6-[3-(4,6-diphenyl-[1,3,5]triazine-2-yl)phenyl]-dibenzofuran-4-yl}-9H-carbazole

[0242] [ka]

[0243] 26 g (70 mmol) of 6-carbazole-9-yl-dibenzofuran-4-boronic acid, 27 g (70 mmol) of 2-(3-bromophenyl)-4,6-diphenyl-[1,3,5]triazine, and 78.9 mL (158 mmol) of Na2CO3 (2M solution) are suspended in 120 mL of ethanol and 100 mL of water. 1.3 g (1.1 mmol) of Pd(PPh3)4 is added to this suspension, and the reaction mixture is heated under reflux for 16 hours. After cooling, dichloromethane is added to the mixture to remove the organic phase, and the mixture is filtered through silica gel. The yield is 39 g (61 mmol), which corresponds to 88% of the theoretical value. The residue is recrystallized from toluene, and finally, under high vacuum (p=5×10⁻⁶), it is subjected to a final filtration. -5 It is sublimated at a rate of millibars. The purity is 99.9%.

[0244] The following compounds can be obtained using a similar method:

[0245] [ka]

[0246] [ka]

[0247] [ka]

[0248] [ka]

[0249] [ka]

[0250] [ka]

[0251] [ka]

[0252] [ka]

[0253] [ka]

[0254] [ka]

[0255] Example 7 Synthesis of 2-(6-bromodibenzofuran-4-yl)-4,6-diphenyl-[1,3,5]triazine

[0256] [ka]

[0257] 14.6 g (45 mmol) of 4,6-dibromobenzofuran, 8.5 g (31.6 mmol) of B-(4,6-diphenyl-1,3,5-triazine-2-yl)boronic acid, and 31 mL (63 mmol) of Na2CO3 (2M solution) are suspended in 120 mL of toluene and 120 mL of ethanol. 0.73 g (0.63 mmol) of Pd(PPh3)4 is added to this suspension, and the reaction mixture is heated under reflux for 16 hours. After cooling, the organic phase is removed, filtered through silica gel, washed three times with 200 mL of water, and then concentrated to dryness. The residue is recrystallized from toluene. The yield is 10.3 g (32 mmol), which corresponds to 77% of the theoretical value.

[0258] The following compounds can be obtained using a similar method:

[0259] [ka]

[0260] [ka]

[0261] [ka]

[0262] Example 8 Synthesis of bis(biphenyl-4-yl)[6-(4,6-diphenyl-[1,3,5]triazine-2-yl)-dibenzofuran-4-yl]amine

[0263] [ka]

[0264] A degassed solution of 84 g (176 mmol) of 2-(6-bromodibenzofuran-4-yl)-4,6-diphenyl-[1,3,5]triazine and 47.41 g (148 mmol) of bis(biphenyl-4-yl)amine in 700 mL of toluene is saturated with N2 for 30 minutes. Then, to this mixture, first, 2.51 mL (10.3 mmol) of 1 M P(tBu)3 solution in toluene is added, followed by 1.66 g (7.3 mmol) of palladium(II) acetate, and then 21.24 g (222 mmol) of solid NaOtBu. The reaction mixture is heated under reflux for 6 hours. After cooling to room temperature, 500 mL of water is carefully added. The aqueous phase is washed three times with 70 mL of toluene, dehydrated with MgSO4, and the solvent is removed under reduced pressure. Subsequently, the crude product was purified by chromatography using silica gel with heptane / ethyl acetate (20:1). The yield was 115 g (160 mmol), which corresponds to 91% of the theoretical value.

[0265] The following compounds can be obtained using a similar method:

[0266] [ka]

[0267] [ka]

[0268] [ka]

[0269] Example 9 Synthesis of biphenyl-4-yl-[5-(4,6-diphenyl-[1,3,5]triazine-2-yl]-9-phenyl-9H-carbazole-4-yl]-{4-[(E)-((Z)-1-propenyl)-buta-1,3-dienyl]-phenyl}amine

[0270] [ka]

[0271] 50 g (70 mmol) of bis(biphenyl-4-yl)[5-(4,6-diphenyl-[1,3,5]triazine-2-yl)-9H-carbazole-4-yl]amine and 16.4 g (105.87 mmol) of bromobenzene are dissolved in toluene and degassed by introducing a protective gas. Subsequently, 4.94 mL (4.94 mmol, 1 M solution in toluene) of tri-tert-butylphosphine, 633.8 mg (2.82 mmol) of Pd(OAc)2, and 10.2 g (105.87 mmol) of NaOtBu are added. The solids are degassed beforehand, the reaction mixture is degassed afterward, and then the mixture is stirred under reflux for 3 hours. The warm reaction solution is then heated in Alox. Filter through B (activity level 1), wash with water, dry, and concentrate. The yield is 42 g (52 mmol), which corresponds to 76% of the theoretical value. The residue is recrystallized from toluene, and finally, under high vacuum (p=5×10⁻⁶). -5 It is sublimated at a rate of millibars. The purity is 99.9%.

[0272] The following compounds can be obtained using a similar method:

[0273] [ka]

[0274] Example 10 Synthesis of comparative compounds The following compounds can be prepared according to WO 2011 / 057706 A2:

[0275] [ka]

[0276] Synthesis of 9-[6-(4,6-diphenyl-[1,3,5]triazine-2-yl]-dibenzofuran-3-yl]-9H-carbazole

[0277] [ka]

[0278] a) The following compounds can be obtained in the same manner as in Example 3:

[0279] [ka]

[0280] b) The following compounds can be obtained in the same manner as in Example 4:

[0281] [ka]

[0282] c) The following compounds can be obtained in the same manner as in Example 5:

[0283] [ka]

[0284] d) The following compounds can be obtained in the same manner as in Example 6:

[0285] [ka]

[0286] Example 15 OLED manufacturing and characterization Examples C1 to I18 below (Tables 1 and 2) present data for various OLEDs.

[0287] Pretreatment for example C1-I18: Glass plaques coated with 50 nm thick structured ITO (indium tin oxide) are coated with 20 nm thick PEDOT:PSS (poly(3,4-ethylenedioxythiophene)poly(styrene sulfonic acid) spun from aqueous solution, purchased from Heraeus Precious Metals GmbH, Germany as CLEVIOS® P VP AI 4083) for improved processing. These coated glass plaques form the substrates to which the OLED is applied.

[0288] An OLED basically has the following layer structure: substrate / hole transport layer (HTL) / optional, intermediate layer (IL) / electron blocking layer (EBL) / emissive layer (EML) / optional, hole blocking layer (HBL) / electron transport layer (ETL) / optional, electron injection layer (EIL), and finally the cathode. The cathode is formed by a 100 nm thick aluminum layer. The exact structure of an OLED can be seen in Table 1. The materials required for the manufacture of an OLED are shown in Table 3.

[0289] All materials are applied by hot vapor deposition in a vacuum chamber. In this case, the luminescent layer always consists of at least one matrix material (host material) and a luminescent dopant (emitter) added to one or more matrix materials in specific volume proportions by co-evaporation. Here, details given in the form of IC1:IC3:TEG1 (55%:35%:10%) mean that material IC1 is present in the layer at a rate of 55 volume%, IC3 at a rate of 35 volume%, and TEG1 at a rate of 10 volume%. Similarly, the electron transport layer may also consist of a mixture of two materials.

[0290] OLEDs are characterized by standard methods. For this purpose, assuming an electroluminescent spectrum and Lambert emission characteristics, the current efficiency (measured in cd / A), power efficiency (measured in Im / W), and external quantum efficiency (EQE, measured in percent) are calculated from the current-voltage-luminance characteristic line (IUL characteristic line) as functions of luminance. The electroluminescent spectrum is calculated with a luminance of 1000 cd / m². 2 The values ​​are measured, and the CIE1931 x and y color coordinates are calculated from them. In Table 2, parameter U1000 corresponds to a luminance of 1000 cd / m². 2 This indicates the voltage required for the following: CE1000 and PE1000 require 1000 cd / m². 2 The current and power efficiencies achieved are shown, respectively. Finally, the EQE1000 has a driving brightness of 1000 cd / m². 2 This shows the external quantum efficiency.

[0291] Table 2 lists data for various OLEDs. Examples C1 and C2 are comparative examples based on prior art, while Examples I1-I18 show data for the OLED of the present invention.

[0292] Several examples will be described in more detail below to demonstrate the advantages of the OLED of the present invention.

[0293] Use of the mixture of the present invention in the light-emitting layer of a phosphorescent OLED When used as a matrix material in phosphorescent OLEDs, the material of the present invention provides a significant improvement in external quantum efficiency compared to the prior art. By using compound 6zzd of the present invention in combination with the green light-emitting dopant TEG1, it is possible to achieve an increase in external quantum efficiency of up to approximately 20% compared to the prior art PA1 (e.g., C1-I1).

[0294] [Table 1]

[0295] [Table 2]

[0296] Table 3-1

[0297] Table 3-2

[0298] Table 3-3

[0299] Table 3-4

Claims

1. Compounds of general formula (3): 【Chemistry 1】 The symbols and subscripts used in the formula are as follows: X is CR １ And; A and A' are either identical or different, and are aromatic ring structures having six ring atoms; ETGs are organic electron transport groups (ETGs) from the group of electron-deficient heterocyclic aromatic groups, and ETGs are selected from the groups of formulas (E-11) to (E-15): 【Chemistry 2】 Z is a single bond, meaning the ETG group is directly bonded to the carbon atom of the A ring; V represents a single bond, meaning that the carbon atoms in rings A and A' are directly bonded to each other by a single bond; W is NR １ , O or S, m = n = 1; R １ Each occurrence may be the same or different, and in each case, there may be one or more R's: H, D, or R's. ２ It is an aromatic ring structure having 5 to 60 aromatic ring atoms that may be substituted by groups; R ２ Each occurrence may be the same or different, and in each case, there may be one or more R's: H, D, or R's. ３ It is an aromatic ring structure having 5 to 60 aromatic ring atoms that may be substituted by groups; R ３ It is either the same or different each time it appears, and is either H or D; R ４ is the same or different for each occurrence, and in each case is an aromatic ring structure having 6 to 60 aromatic ring atoms which may be substituted by one or more R ２ groups; two or more adjacent R ４ groups may together form a monocyclic or polycyclic heterocyclic aromatic ring structure.

2. R １ The compound according to claim 1, characterized in that is H and D.

3. The compound according to claim 1 or 2, characterized in that it is a compound of the following general formula (5): 【Transformation 3】 In the formula, the substituents are as defined in claim 1.

4. The compound according to claim 1 or 2, characterized in that ETG is selected from the group of formula (E-11): 【Chemistry 4】 In the formula, R １ This is as defined in claim 1.

5. A composition comprising at least one compound according to any one of claims 1 to 4, and at least one additional compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, host materials, matrix materials, electron transport materials, electron injection materials, hole conduction materials, hole injection materials, electron blocking materials, and hole blocking materials.

6. The composition according to claim 5, characterized in that the additional compound is a host material or a matrix material.

7. The composition according to claim 5 or 6, characterized in that the additional compound has a band gap of 2.5 eV or more.

8. An electronic element comprising at least one compound according to any one of claims 1 to 4 or at least one composition according to any one of claims 5 to 7.

9. The electronic element according to claim 8, characterized by being selected from organic integrated circuits (O-IC), organic field-effect transistors (O-FET), organic thin-film transistors (O-TFT), organic electroluminescent elements, organic solar cells (O-SC), organic optical inspection elements, and organic photoreceptors.

10. The electronic element according to claim 9, characterized in that it is an organic electroluminescent element.

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