Materials for organic electroluminescent devices

Abstract

To provide dibenzofuran derivatives which are substituted with electron-poor heteroaryl groups, and electronic devices.SOLUTION: A compound represented by formula (1) is provided. (In the formula, Y is O or S; Z is CR or N, provided that at least two Z's are N; Ar1 is an aromatic ring system having 6 to 40 aromatic ring atoms or the like; Ar2 is an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms; and R is H, D, F, Cl, Br, I, N(R1)2, or the like).SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention describes dibenzofuran derivatives which are substituted by electron-deficient heteroaromatic systems and electronic devices comprising these compounds, in particular organic electroluminescent devices comprising these compounds as triplet matrix materials. 2. Background of the Invention Phosphorescent organometallic complexes are often used in organic electroluminescent devices (OLEDs). In general, there is still a need to improve OLEDs, for example with respect to efficiency, operating voltage and lifetime. The properties of phosphorescent OLEDs are not only determined by the triplet emitter used. More specifically, other materials used, such as matrix materials, are also of particular importance here. Therefore, improvements in these materials can also lead to clear improvements in OLED properties. Summary of the Invention According to the prior art, matrix materials for use with phosphorescent emitters include carbazole derivatives, dibenzofuran derivatives, indenocarbazole derivatives and indolocarbazole derivatives, especially those substituted with electron-deficient heteroaromatic systems, such as triazines. In general, there is still a need for improvements of these materials for use as matrix materials. The problem addressed by the present invention is the provision of compounds that are particularly suitable for use as matrix materials in phosphorescent OLEDs. More particularly, it is an object of the present invention to provide matrix materials that result in improved lifetimes. This applies in particular to the use of low to medium emitter concentrations, i.e. of the order of magnitude of 3% to 20%, especially 3% to 15%, since the device lifetime is particularly limited here.

[0002] Surprisingly, it has been found that electroluminescent devices containing a compound of the following formula (1) have improvements over the prior art, especially when this compound is used as a matrix material for a phosphorescent dopant.

[0003] Thus, the present invention provides a compound of formula (1):

[0004] [ka]

[0005] (wherein the symbols used are as follows: Y is O or S; Z, at each occurrence, is the same or different, and is CR or N, with the proviso that at least two Z are N; Ar 1 are the same or different in each occurrence and are an aromatic ring system having 6 to 40 aromatic ring atoms which may be substituted by one or more R radicals, or a heteroaromatic ring system having 5 to 40 aromatic ring atoms which is linked to the dibenzofuran or dibenzothiophene via a nitrogen atom and which may be substituted by one or more R radicals, or a dibenzofuran or dibenzothiophene group which may be substituted by one or more R radicals; Ar 2 is the same or different in each occurrence and is an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, optionally substituted by one or more R radicals; R is the same or different in each occurrence and is H, D, F, Cl, Br, I, N(Ar'), N(R 1 )2, OAr', SAr', CN, NO2, OR 1 , S.R. 1 , COOR 1 , C(=O)N(R 1 )2, Si(R 1 )3, B(OR 1 )2, C(=O)R 1 , P(=O)(R 1 )2, S(=O)R 1 , S(=O)2R 1 , OSO2R 1, a linear alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group is in each case composed of one or more R 1 radicals) (wherein one or more non-adjacent CH groups are optionally substituted with Si(R 1 )2, C=O, NR 1 , O, S or CONR 1 or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, in each case one or more R 1 at the same time, the two R radicals may also together form a ring system; Ar', in each occurrence, is the same or different, and is an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, and one or more R 1 At the same time, two Ar′ radicals attached to the same nitrogen atom may also be substituted by a single bond or an N(R 1 ), C(R 1 ) 2, may be crosslinked to each other by bridges selected from O and S; R 1 are the same or different in each case and are H, D, F, Cl, Br, I, N(R 2 )2, CN, NO2, OR 2 , S.R. 2 , 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 group having 1 to 20 carbon atoms, or an alkenyl or alkynyl group having 2 to 20 carbon atoms, or a branched or cyclic alkyl group having 3 to 20 carbon atoms, wherein the alkyl, alkenyl or alkynyl group is each selected from the group consisting of one or more R 2radicals) (wherein one or more non-adjacent CH groups are optionally substituted with Si(R 2 )2, C=O, NR 2 , O, S or CONR 2 and one or more hydrogen atoms in an alkyl, alkenyl or alkynyl group may be replaced by D, F, Cl, Br, I or CN), or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, in each case one or more R 2 At the same time, two or more R 1 the radicals together may form an aliphatic ring system; R 2 is in each occurrence the same or different and is H, D, F, CN, or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 carbon atoms, in particular a hydrocarbyl radical, in which one or more hydrogen atoms may also be replaced by F; p, q, in each occurrence, are the same or different and are 0, 1, 2 or 3; r is 0, 1, 2, 3, or 4, with the proviso that r is less than or equal to (4-j); s is 0, 1, 2, or 3, with the proviso that s is less than or equal to (3-k); j, k are the same or different in each occurrence and are 0, 1, 2, or 3, with the proviso that j+k≧1. to provide.

[0006] An aryl group in the context of the present invention contains 6 to 40 carbon atoms; a heteroaryl group in the context of the present invention contains 2 to 40 carbon atoms and at least one heteroatom, with the sum of carbon atoms and heteroatoms being at least 5. The heteroatoms are preferably selected from N, O and / or S. An aryl or heteroaryl group here is understood to mean either a simple aromatic ring, i.e. benzene, or a simple heteroaromatic ring, such as pyridine, pyrimidine, thiophene, etc., or a condensed (condensed ring) aryl or heteroaryl group, such as naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc. Aromatic systems which are linked together by a single bond, such as biphenyl, on the other hand, are not called aryl or heteroaryl groups, but aromatic ring systems.

[0007] Aromatic ring systems in the context of the present invention contain 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, in the ring system. Heteroaromatic ring systems in the context of the present invention contain 2 to 60 carbon atoms, preferably 2 to 40 carbon atoms, and at least one heteroatom, with the sum of carbon atoms and heteroatoms being at least 5. The heteroatoms are preferably selected from N, O and / or S. Aromatic or heteroaromatic ring systems in the context of the present invention are of course understood to mean systems which do not necessarily contain only aryl or heteroaryl groups, but in which two or more aryl or heteroaryl groups can also be linked by non-aromatic units, such as carbon, nitrogen or oxygen atoms. They are likewise of course understood to mean systems in which two or more aryl or heteroaryl groups, such as biphenyl, terphenyl, bipyridine or phenylpyridine, are directly linked to each other. For example, systems such as fluorene, 9,9'-spirobifluorene, 9,9'-diarylfluorene, triarylamines, diaryl ethers, stilbenes, etc. are also considered to be aromatic ring systems in the context of the present invention, as are systems in which two or more aryl groups are linked, for example by short alkyl groups. Preferred aromatic or heteroaromatic ring systems are simple aryl or heteroaryl groups as well as groups in which two or more aryl or heteroaryl groups are directly linked to one another, such as biphenyl or bipyridine, and also fluorene or spirobifluorene.

[0008] Alkyl groups in the context of the present invention also include cycloalkyl groups, and alkenyl groups in the context of the present invention also include cycloalkenyl groups. In the context of the present invention, aliphatic hydrocarbyl radicals or alkyl groups or alkenyl or alkynyl groups, which may contain 1 to 40 carbon atoms and in which individual hydrogen atoms or CH2 groups may be replaced by the abovementioned groups, are preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclo ... cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl radicals. 1 is preferably understood to mean 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 and 2,2,2-trifluoroethoxy. Thioalkyl groups SR having 1 to 40 carbon atoms 1is understood to mean in particular methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, n-pentylthio, s-pentylthio, n-hexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, cyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthio, cyclooctenylthio, ethynylthio, propynylthio, butynylthio, pentynylthio, hexynylthio, heptynylthio or octynylthio. In general, an alkyl, alkoxy or thioalkyl group according to the present invention may be linear, branched or cyclic, in which one or more non-adjacent CH groups may be replaced by the groups mentioned above; in addition, one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO, preferably F, Cl or CN, more preferably F or CN.

[0009] 5 to 60 aromatic ring atoms, in each case as defined above for R 2The aromatic or heteroaromatic ring systems, which may be substituted by radicals or hydrocarbyl radicals and which may be linked to the aromatic or heteroaromatic system via any desired position, are in particular benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or tran- s-Indenofluorene, cis- or trans-indenocarbazole, cis- or trans-indolocarbazole, truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8- Quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridiimidazole, pyrazineimidazole, quinoxalineimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, hexaazatriphenylene, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1,5 -diazaanthracene, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazapyrylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorubine, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,It is understood to mean radicals derived from 2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine and benzothiadiazole, or combinations of these systems.

[0010] The expression that two or more radicals may together form a ring system is understood to mean the formation of an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system, and in the context of this specification is understood to mean, inter alia, that two radicals are linked to each other by a chemical bond, with the formal removal of two hydrogen atoms. This is illustrated by the following scheme:

[0011] [ka]

[0012] However, in addition, the above expression should also be understood to mean that if one of the two radicals is hydrogen, the second radical is bonded to the position to which the hydrogen atom is bonded to form a ring. This is illustrated by the following scheme:

[0013] [ka]

[0014] In preferred aspects of the invention, either all three Z groups are N, or two Z groups are N and the third Z group is CH. In particularly preferred aspects of the invention, all Z groups are N. Thus, the group is more preferably a diaryltriazine group.

[0015] Thus, in a preferred embodiment of the present invention, the group incorporated in formula (1)

[0016] [ka]

[0017] is selected from the following groups (HetAr-1), (HetAr-2) and (HetAr-3):

[0018] [ka]

[0019] (In the formula, Ar 2 has the definition above and the dotted bond indicates the attachment of this group).

[0020] (HetAr-1) is particularly preferred, and therefore the compound of formula (1) is preferably a compound of formula (2) below:

[0021] [ka]

[0022] (wherein the symbols and subscripts used have the definitions given above).

[0023] In a further preferred embodiment of the invention, Y is O and therefore the compound has one of the following formulas (3):

[0024] [ka]

[0025] (wherein the symbols and subscripts used have the definitions given above).

[0026] More preferably, all Z are N and simultaneously Y is O, and thus the compound is one of the following formulas (4):

[0027] [ka]

[0028] (wherein the symbols and subscripts used have the definitions given above).

[0029] In further preferred embodiments of the compounds of formulae (1), (2), (3) and (4), r and s are the same or different in each occurrence and are 0 or 1, more preferably 0. In further preferred embodiments of the compounds of formulae (1), (2), (3) and (4), p and q are the same or different in each occurrence and are 0, 1 or 2, more preferably 0 or 1, most preferably 0. Thus, more preferably, the dibenzofuran group does not have an R radical and the compound is one of the following formulae (5):

[0030] [ka]

[0031] (wherein the symbols and subscripts used have the definitions given above).

[0032] In a further preferred embodiment of the invention, j and k in the compounds of formulae (1), (2), (3), (4) and (5) are in each case the same or different and are 0, 1 or 2, more preferably 0 or 1, with the proviso that j+k≧1. Most preferably, j+k=1, and thus the compounds contain exactly one Ar 1 In one embodiment of the invention, j=1 and k=0, and in a further embodiment, j=0 and k=1, with the embodiment where j=1 and k=0 being particularly preferred. Thus, compounds of the following formulae (6a) and (6b) are preferred:

[0033] [ka]

[0034] (wherein the symbols and subscripts used have the definitions given above).

[0035] Particularly preferred are compounds of one of the following formulae (7a) and (7b):

[0036] [ka]

[0037] (wherein the symbols used have the meanings given above).

[0038] When j=1, Ar in compounds of formulas (1), (2), (3), (4), (5), (6a), (6b), (7a) and (7b) 1 The group is preferably attached at the 7- or 8-position of the dibenzofuran or dibenzothiophene, more preferably at the 8-position. More preferably, when k=1, the Ar 1 The group is preferably attached at the 3- or 4-position of the dibenzofuran or dibenzothiophene, more preferably at the 4-position.

[0039] The numbering for dibenzofuran is shown in the following scheme, and the numbering for dibenzothiophene is similar:

[0040] [ka]

[0041] Very particular preference is given to structures of the following formula (8a) or (8b):

[0042] [ka]

[0043] (wherein the symbols used have the meanings given above).

[0044] In a preferred embodiment of the present invention, Ar 2 are in each occurrence the same or different, aromatic or heteroaromatic ring systems having 6 to 30 aromatic ring atoms, optionally substituted by one or more R radicals. More preferably, Ar 2 are in each case the same or different and are aromatic or heteroaromatic ring systems, especially aromatic ring systems, having 6 to 24 aromatic ring atoms, especially 6 to 13 aromatic ring atoms, optionally substituted by one or more, preferably non-aromatic, R radicals. 2 When is a heteroaryl group, especially a triazine, pyrimidine, quinazoline or carbazole, the aromatic or heteroaromatic substituents R on the heteroaryl group may also be selected.

[0045] Suitable aromatic or heteroaromatic ring systems Ar 2 are in each case the same or different and are selected from phenyl, biphenyl, especially ortho-, meta- or para-biphenyl, terphenyl, especially ortho-, meta- or para-terphenyl or branched terphenyl, quaterphenyl, especially ortho-, meta- or para-quaterphenyl or branched quaterphenyl, fluorene optionally bonded via 1, 2, 3 or 4 position, spirobifluorene optionally bonded via 1, 2, 3 or 4 position, naphthalene optionally bonded via 1 or 2 position, indole, benzofuran, benzothiophene, carbazole optionally bonded via 1, 2, 3 or 4 position, dibenzofuran optionally bonded via 1, 2, 3 or 4 position, dibenzothiophene optionally bonded via 1, 2, 3 or 4 position, indenocarbazole, indolocarbazole, phenanthrene, triphenylene, or a combination of two or three of these groups, each of which may be substituted by one or more R radicals, preferably non-aromatic R radicals. 2When is a heteroaryl group, especially a triazine, pyrimidine, quinazoline or carbazole, the R radicals on the heteroaryl group may also be selected to be aromatic or heteroaromatic.

[0046] Preferably, Ar here 2 are in each case the same or different and are selected from the group of the following formulae Ar-1 to Ar-81:

[0047] [ka]

[0048] [ka]

[0049] [ka]

[0050] [ka]

[0051] [ka]

[0052] where R is as defined above, the dotted bond represents a bond to the heteroaryl group, and additionally: A 1 is the same or different in each occurrence and is CR2, NR, O, or S; Ar 3 is the same or different, in each occurrence, a divalent aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, in each occurrence optionally substituted by one or more R radicals; n is 0 or 1, where n=0 is A 1means that no group is attached at this position, but instead the R radical is attached to the corresponding carbon atom; m is 0 or 1, where m=0 is Ar 3 This means that the group is absent and the corresponding aromatic or heteroaromatic group is directly bonded to the triazine or pyrimidine group in formula (1).

[0053] In a further preferred embodiment of the present invention, Ar 1 is an aromatic ring system having 6 to 30 aromatic ring atoms and optionally substituted by one or more R radicals, or N-carbazolyl optionally substituted by one or more R radicals, or dibenzofuran or dibenzothiophene, each optionally substituted by one or more R radicals. More preferably, Ar 1 is an aromatic ring system having 6 to 24 aromatic ring atoms, in particular 6 to 18 aromatic ring atoms, optionally substituted by one or more, preferably non-aromatic, R radicals, or a dibenzofuran group optionally substituted by one or more R radicals.

[0054] Suitable Ar 1 The radicals are selected from phenyl, biphenyl, especially ortho-, meta- or para-biphenyl, terphenyl, especially ortho-, meta- or para-terphenyl or branched terphenyl, quaterphenyl, especially ortho-, meta- or para-quaterphenyl or branched quaterphenyl, fluorene optionally bonded via the 1, 2, 3 or 4 position, spirobifluorene optionally bonded via the 1, 2, 3 or 4 position, naphthalene optionally bonded via the 1 or 2 position, N-carbazole, dibenzofuran optionally bonded via the 1, 2, 3 or 4 position, dibenzothiophene optionally bonded via the 1, 2, 3 or 4 position, phenanthrene, triphenylene, or a combination of two or three of these radicals, each of which may be substituted by one or more R radicals.

[0055] Here, Ar 1are preferably in each case the same or different and are selected from the groups of the following formulae Ar-1 to Ar-16, Ar-43 to Ar-46 and Ar-69 to Ar-75:

[0056] [ka]

[0057] [ka]

[0058] [ka]

[0059] where R has the definition above and the dotted bond represents the bond to the dibenzofuran or dibenzothiophene, and additionally: A 1 is the same or different in each occurrence and is CR2, O, or S; Ar 3 is the same or different, in each occurrence, a divalent aromatic ring system having 6 to 18 aromatic ring atoms, in each occurrence optionally substituted by one or more R radicals; n is 0 or 1; m is 0 or 1, where m=0 is Ar 3 (meaning that the aryl group is absent and the corresponding aromatic or heteroaromatic group is directly attached to the dibenzofuran or dibenzothiophene).

[0060] In a preferred embodiment of the invention, R is the same or different in each occurrence and is selected from the group consisting of H, D, F, N(Ar′), CN, OR 1 , a linear alkyl group having 1 to 10 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein the alkyl or alkenyl group is each selected from the group consisting of one or more R1 radicals, but preferably unsubstituted, wherein one or more non-adjacent CH groups are optionally replaced by O, or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, in each case selected from the group consisting of 1 at the same time, two R radicals together may also form an aliphatic, aromatic or heteroaromatic ring system. More preferably, R is in each case the same or different and is H, N(Ar')2, a linear alkyl group having 1 to 6 carbon atoms, in particular 1, 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group having 3 to 6 carbon atoms, where the alkyl group in each case is one or more R 1 radicals, but preferably unsubstituted), or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, in each case selected from the group consisting of one or more R 1 A radical, preferably non-aromatic R 1 Most preferably, R, in each occurrence, is the same or different and is selected from the group consisting of H, or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, and in each occurrence, one or more R 1 A radical, preferably non-aromatic R 1 It may be substituted by a radical.

[0061] In a further preferred embodiment of the invention, Ar' is an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms and is selected from the group consisting of one or more R 1 In a particularly preferred embodiment of the invention, Ar' is an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, in particular 6 to 13 aromatic ring atoms, and is optionally substituted by one or more, preferably non-aromatic R 1 It may be substituted by a radical.

[0062] Suitable aromatic or heteroaromatic ring systems R or Ar' are phenyl, biphenyl, especially ortho-, meta- or para-biphenyl, terphenyl, especially ortho-, meta- or para-terphenyl or branched terphenyl, quaterphenyl, especially ortho-, meta- or para-quaterphenyl or branched quaterphenyl, fluorene, which may be bonded via the 1, 2, 3 or 4 position, spirobifluorene, which may be bonded via the 1, 2, 3 or 4 position, naphthalene, which may be bonded via the 1 or 2 position, indole, benzofuran, benzothiophene, carbazole optionally bonded through position 1, 2, 3 or 4, dibenzofuran optionally bonded through position 1, 2, 3 or 4, dibenzothiophene optionally bonded through position 1, 2, 3 or 4, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinazoline, benzimidazole, phenanthrene, triphenylene or a combination of two or three of these groups, each of which is selected from one or more non-aromatic R 1 When R or Ar' is a heteroaryl group, especially a triazine, pyrimidine or quinazoline, an aromatic or heteroaromatic R 1 The radicals may also be selected.

[0063] The R group here (in the case of an aromatic or heteroaromatic ring system), or Ar′, is preferably selected from the groups of the following formulae R-1 to R-81:

[0064] [ka]

[0065] [ka]

[0066] [ka]

[0067] [ka]

[0068] [ka]

[0069] [ka]

[0070] (where R 1 has the above definition, and the dotted bond indicates a bond to a carbon atom of the base skeleton of formula (1) or in a preferred embodiment, or to Ar 1 Or Ar 2 or to the nitrogen atom of an N(Ar')2 group, in addition: Ar 3 are the same or different, in each occurrence, a divalent aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, and in each occurrence one or more R 1 may be substituted with a radical; A 1 are the same or different in each case, and C(R 1 )2, NR 1 , O or S; n is 0 or 1, where n=0 means that no A group is attached at this position and instead R 1 means that the radical is attached to the corresponding carbon atom; m is 0 or 1, where m=0 is Ar 3It means that the group is absent and the corresponding aromatic or heteroaromatic group is directly bonded to a carbon atom of the base skeleton of formula (1) or in the preferred embodiments, or to a nitrogen atom of the N(Ar') group; provided that when these groups are in the Ar' embodiment, m=1 for structures (R-12), (R-17), (R-21), (R-25), (R-26), (R-30), (R-34), (R-38) and (R-39).

[0071] Ar 1 Or Ar 2 The above-mentioned Ar-1 to Ar-81 groups for R or Ar', or R-1 to R-81 for R or Ar', 1 If the aryl group is present, these possible options include A 1 In this case, a preferred embodiment is one of A 1 The group is NR or NR 1 And the other A 1 The group is C(R)2 or C(R 1 )2 or both A 1 The group is NR or NR 1 or both A 1 In a particularly preferred embodiment of the present invention, two or more A groups are 1 Ar having a group 1 , Ar 2 In the R or Ar' group, at least one A 1 The group is C(R)2 or C(R 1 )2 or NR or NR 1 It is.

[0072] A 1 NR or NR 1 In the case of 1 is preferably an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, and one or more R 1 or R 2 In a particularly preferred embodiment, R or R 1The substituents are in each case the same or different and are aromatic or heteroaromatic ring systems having 6 to 24 aromatic ring atoms, preferably 6 to 12 aromatic ring atoms, not including fused aryl or heteroaryl groups in which two or more aromatic or heteroaromatic six-membered ring groups are directly fused to each other, and in each case one or more R 1 or R 2 Particularly preferred are phenyl, biphenyl, terphenyl and quaterphenyl having bonding patterns as listed above for Ar-1 to Ar-11 or R-1 to R-11, where these structures may be substituted by one or more R 1 or R 2 It may be substituted with a radical, but is preferably unsubstituted.

[0073] A 1 is C(R)2 or C(R 1 )2, the substituent R or R bonded to this carbon atom 1 are preferably in each case the same or different and are a linear alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, and one or more R 1 or R 2 It may be substituted by a radical. Most preferably, it is R or R 1 is a methyl group or a phenyl group. In this case, R or R 1 The radicals may also form a ring system together, resulting in a spiro system.

[0074] In a further preferred embodiment of the present invention, R 1 are the same or different in each case, H, D, F, CN, OR 2 , a linear alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the alkyl or alkenyl group is in each case one or more R 2radicals), in which one or more non-adjacent CH groups are optionally replaced by O, or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, in each case selected from the group consisting of one or more R 2 At the same time, two or more R 1 The radicals may also together form an aliphatic ring system. In a particularly preferred embodiment of the invention, R 1 are in each case the same or different and are H, a linear alkyl group having 1 to 6 carbon atoms, in particular 1, 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group having 3 to 6 carbon atoms, where the alkyl group is selected from one or more R 2 radicals, but preferably unsubstituted), or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, in each case selected from the group consisting of one or more R 2 It may be substituted with a radical, but is preferably unsubstituted.

[0075] In a further preferred embodiment of the present invention, R 2 is in each occurrence the same or different and is H, F, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms, which may be substituted by an alkyl group having 1 to 4 carbon atoms, but is preferably unsubstituted.

[0076] The above preferences may occur individually or together. The above preferences are preferred when they occur together.

[0077] Examples of suitable compounds of the invention are those with the structures depicted below:

[0078] [ka]

[0079] [ka]

[0080]

change

[0081]

change

[0082]

change

[0083]

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[0084]

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[0112] The compounds of the present invention can be prepared by synthetic steps known to those skilled in the art, such as bromination, Suzuki coupling, Ullmann coupling, Hartwig-Buchwald coupling, etc. A suitable synthetic method is illustrated in general terms in Scheme 1 below, where the symbols and indices used have the definitions given above.

[0113] [ka]

[0114] In order to process the compounds of the invention from a liquid phase, for example by spin-coating or printing methods, formulations of the compounds of the invention are required. These formulations may be, for example, solutions, dispersions or emulsions. For this purpose, it may be preferable to use a mixture of two or more solvents. Suitable preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, α-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, NMP, p- cymene, phenetole, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, 2-methylbiphenyl, 3-methylbiphenyl, 1-methylnaphthalene, 1-ethylnaphthalene, ethyl octanoate, diethyl sebacate, octyl octanoate, heptylbenzene, methyl isovalerate, cyclohexyl hexanoate or a mixture of these solvents.

[0115] Thus, the present invention further provides a formulation comprising at least one compound of the present invention and at least one further compound.The further compound may be, for example, a solvent, in particular one of the above-mentioned solvents or a mixture of these solvents.The further compound may alternatively be at least one further organic or inorganic compound, such as a light-emitting compound and / or a further matrix material, which are also used in electronic devices.Suitable light-emitting compounds and further matrix materials are listed below in connection with organic electroluminescent devices.The further compound may also be a polymer.

[0116] The compounds of the present invention are suitable for use in electronic devices, especially organic electroluminescent devices.Thus, the present invention further provides the use of the compounds of the present invention in electronic devices, especially organic electroluminescent devices.

[0117] The present invention still further provides an electronic device comprising at least one compound of the present invention.

[0118] The electronic device according to the invention is a device comprising at least one layer containing at least one organic compound. This component may also comprise layers formed from inorganic materials or entirely inorganic materials. The electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field effect transistors (O-FETs), organic thin film transistors (O-TFTs), organic light emitting transistors (O-LETs), organic solar cells (O-SCs), dye-sensitized organic solar cells (DSSCs), organic photodetectors, organic photoreceptors, organic field quenching devices (O-FQDs), light emitting electrochemical cells (LECs), organic laser diodes (O-lasers) and organic plasmonic light emitting devices, but is preferably an organic electroluminescent device (OLED), more preferably a phosphorescent OLED.

[0119] The organic electroluminescent device comprises a cathode, an anode and at least one light-emitting layer. Besides these layers, it may also comprise further layers, for example in each case one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers and / or charge generating layers. It is also possible to introduce an intermediate layer with exciton blocking function, for example between two light-emitting layers. However, it should be pointed out that not all of these layers necessarily have to be present. In this case, it is possible that the organic electroluminescent device contains a light-emitting layer or that it contains several light-emitting layers. If several light-emitting layers are present, these preferably have several emission maxima in the range 380 nm to 750 nm as a whole, so that the overall result is a white emission; in other words, various light-emitting compounds that can fluoresce or phosphoresce are used in the light-emitting layers. Particularly preferred are systems with three light-emitting layers, where the three layers show blue, green and orange or red emission. The organic electroluminescent device of the present invention may also be a tandem OLED, especially in the case of a white-emitting OLED.

[0120] The compounds of the present invention according to the above detailed embodiments may be used in different layers based on the exact structure. Organic electroluminescent devices are preferred that contain the compound of formula (1) or the preferred embodiments listed above in the emitting layer as a matrix material for phosphorescent emitters or emitters that exhibit TADF (thermally activated delayed fluorescence), especially phosphorescent emitters. In this case, the organic electroluminescent device may contain an emitting layer, or it may contain multiple emitting layers, where at least one emitting layer contains at least one compound of the present invention as a matrix material. Furthermore, the compounds of the present invention may also be used in the electron transport layer and / or hole blocking layer.

[0121] When the compounds of the present invention are used as matrix materials of phosphorescent compounds in the light-emitting layer, they are preferably used in combination with one or more phosphorescent materials (triplet emitters).Phosphorescence in the context of the present invention is understood to mean luminescence from excited states with higher spin multiplicity, i.e. spin states>1, especially excited triplet states.In the context of this application, all luminescent complexes containing transition metals or lanthanides, especially all iridium, platinum and copper complexes, will be considered as phosphorescent compounds.

[0122] Examples of the above mentioned phosphors are disclosed in applications WO 00 / 70655, WO 2001 / 41512, WO 2002 / 02714, WO 2002 / 15645, EP 1191613, EP 1191612, EP 1191614, WO 05 / 033244, WO 05 / 019373, US 2005 / 0258742, WO 2009 / 146770, WO 2010 / 015307, WO 2010 / 031485, WO 2010 / 054731, WO 2010 / 054728, WO 2010 / 086089, WO 2010 / 099852, WO 2010 / 102709, WO 2011 / 032626, WO 2011 / 066898, WO 2011 / 157339, WO 2012 / 007086, WO 2014 / 008982, WO 2014 / 023377, WO 2014 / 094961, WO 2014 / 094960, WO 2015 / 036074, WO 2015 / 104045, WO 2015 / 117718, WO 2016 / 015815, WO 2016 / 124304, WO 2017 / 032439, WO 2018 / 011186 and WO 2018 / 041769, WO 2019 / 020538, WO 2018 / 178001, WO 2019 / 115423 and WO 2019 / 158453. In general, all phosphorescent complexes as used in phosphorescent OLEDs according to the prior art and known to those skilled in the art of organic electroluminescence are suitable, and those skilled in the art will be able to use further phosphorescent complexes without using the technology of the present invention.

[0123] Examples of phosphorescent dopants are given below.

[0124] [ka]

[0125] [ka]

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[0129] [ka]

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[0134] [ka]

[0135] The mixture of the compound of the present invention and the light-emitting compound contains 99% to 1% by volume, preferably 98% to 10% by volume, more preferably 97% to 60% by volume, especially 95% to 80% by volume of the compound of the present invention based on the entire mixture of the light-emitting body and the matrix material, whereas the mixture contains 1% to 99% by volume, preferably 2% to 90% by volume, more preferably 3% to 40% by volume, especially 5% to 20% by volume of the light-emitting body based on the entire mixture of the light-emitting body and the matrix material.

[0136] A further preferred embodiment of the present invention is the use of the compounds of the present invention as a matrix material for phosphorescent emitters in combination with further matrix materials.Suitable matrix materials that can be used in combination with the compounds of the present invention include, for example, aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones according to WO 2004 / 013080, WO 2004 / 093207, WO 2006 / 005627 or WO 2010 / 006680, triarylamines, carbazole derivatives, such as CBP(N,N-biscarbazolylbiphenyl) or carbazole derivatives as disclosed in WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 288381, EP 1205527, WO 2008 / 086851 or WO 2013 / 041176, for example indolocarbazole derivatives according to WO 2007 / 063754 or WO 2008 / 056746, for example indenocarbazole derivatives according to WO 2010 / 136109, WO 2011 / 000455, WO 2013 / 041176 or WO 2013 / 056776, for example EP 1617710, EP 1617711, EP 1731584, JP azacarbazole derivatives according to, for example, WO 2005 / 347160, bipolar matrix materials according to, for example, WO 2007 / 137725, silanes according to, for example, WO 2005 / 111172, azaboroles or boronic esters according to, for example, WO 2006 / 117052, triazine derivatives according to, for example, WO 2007 / 063754, WO 2008 / 056746, WO 2010 / 015306, WO 2011 / 057706, WO 2011 / 060859 or WO 2011 / 060877, zinc complexes according to, for example, EP 652273 or WO 2009 / 062578, diazasilol or tetraazasilol derivatives according to, for example, WO 2010 / 054729, 2010 / 054730, bridged carbazole derivatives, for example, according to WO 2011 / 042107, WO 2011 / 060867, WO 2011 / 088877 and WO 2012 / 143080, triphenylene derivatives, for example, according to WO 2012 / 048781 or dibenzofuran derivatives, for example, according to WO 2015 / 169412, WO 2016 / 015810, WO 2016 / 023608, WO 2017 / 148564 or WO 2017 / 148565. It is also possible for additional phosphorescent emitters having shorter wavelength emission than the actual emitter to be present in the mixture as co-hosts or compounds that do not participate to a significant extent, if at all, in the charge transport, as described, for example, in WO 2010 / 108579.

[0137] In a preferred embodiment of the present invention, the material is used in combination with a further matrix material, in particular a hole-transporting matrix material. Preferred co-matrix materials are selected from the group of carbazole and triarylamine derivatives, in particular biscarbazoles, bridged carbazoles, triarylamines, dibenzofuran-carbazole derivatives or dibenzofuran-amine derivatives, and carbazole amines.

[0138] A preferred hole-transporting matrix material is a compound of formula (9):

[0139] [ka]

[0140] (In the formula, R, R 1 , R 2 and Ar′ have the definitions detailed above, with the additional symbols and subscripts used being as follows: R A ,H,-L 3 -Ar 5 or -L 1 -N(Ar')2; R B Ar 4 or -L 2 -N(Ar')2; L 1 , L 2 are the same or different in each occurrence and are a single bond or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, and one or more R 1 may be substituted with a radical; L 3 is a single bond or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, and one or more R 2 may be substituted by radicals, where one substituent R 1 may form a ring with the substituent R on the carbazole; Ar4 is an aromatic ring system having 6 to 40 aromatic ring atoms, or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be joined by one or more R 1 may be substituted with a radical; Ar 5 are the same or different in each occurrence and are unsubstituted or substituted 9-arylcarbazolyl or unsubstituted or substituted carbazol-9-yl, which may be represented by one or more R 1 radical, where one or more of the two R 1 Each radical is or one R 1 The radicals may independently form, together with one R radical, a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring, where aryl is an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms and R 1 may be substituted by; u is independently at each occurrence 0, 1, 2 or 3; v is independently in each occurrence 0, 1, 2, 3, or 4.

[0141] The compounds of formula (9) may be represented by the following formulae (9a), (9b), (9c) and (9d):

[0142] [ka]

[0143] (In the formula, L 1 , L 2 , L 3 , Ar', Ar 4 , Ar 5 , R, u and v have the definitions above or below.

[0144] Preferred compounds of formula (9) or (9a) are compounds of formula (9e), (9f), (9g), (9h) and (9i)

[0145] [ka]

[0146] [ka]

[0147] (where R B , Ar', R, R 1 , R 2 , u and v have the above or following definitions, and L in formulas (9h) and (9i) 3 is an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms and one or more R 1 radicals, where one substituent R on the carbazole is a substituent R 1 and the ring (X=C(R 1 )2, NAr', O or S and t=0 or 1) may be formed).

[0148] In the compounds of formulae (9), (9a), (9b), (9c), (9d), (9e), (9f), (9g), (9h) and (9i), one substituent R and one substituent R 1 For example, [X] in formula (9f) t and preferably form the following rings X-1 to X-7, where the dotted line in each case represents the bond to the carbazole:

[0149] [ka]

[0150] In the compounds of formulae (9), (9a), (9b), (9c), (9d), (9e), (9f), (9g), (9h) and (9i), in one or more cases two substituents R may be taken together to form a ring or in one or more cases two substituents R 1may form a ring preferably selected from the following structures (S1) to (S9), where # and # represent the respective bonding sites to the carbon atoms, and these structures may be joined by one or more substituents R 1 may be respectively replaced by:

[0151] [ka]

[0152] R in partial structures (S1) to (S9) 1 is preferably H or an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, R 2 The structures (S1) to (S9) may be substituted by two substituents R 1 When the structures are structures resulting from ring formation with R 1 R rather than by 2 is replaced by

[0153] In the compounds of formula (9), (9a), (9b), (9c), (9d), (9e), (9f), (9g), (9h) and (9i), the linker L 1 , L 2 and L 3 is not a single bond, is independently selected from the linkers L-2.1 to L-2.33:

[0154] [ka]

[0155] [ka]

[0156] [ka]

[0157] where W is NAr′, O, S or C(CH3)2, Ar′ has the above definition, and the linkers L-2.1 to L-2.33 are each selected from one or more R 1 The linker L may be substituted with a radical, and the dotted line represents the bond to the carbazole. 3 In this case, R in one of the linkers L-2.1 to L-2.33 1 The radical may form a ring with the R radical of the carbazole.

[0158] Preferably, the linkers L-2.1 to L-2.33 are unsubstituted or substituted by phenyl.

[0159] L 1 Preferred linkers in this case are selected from structures L-2.1 to L-2.33, where W is defined as S or O, more preferably as O.

[0160] L 3 Preferred linkers in this case are selected from structures L-2.1 to L-2.33, where W is defined as O, S or NAr', more preferably O or NAr'.

[0161] In preferred embodiments of the compounds of formulae (9), (9a), (9b), (9c), (9d), (9e), (9f), (9g), (9h) and (9i), the two carbazoles are bonded to each other at the 3-position.

[0162] In the compounds of formula (9), (9a), (9b), (9c), (9d), (9e), (9f), (9g), (9h) and (9i), u is preferably 0, 1 or 2 and R has the above or following definition. More preferably, u=0 or 1. Most preferably, u=0.

[0163] In the compounds of formulae (9), (9a), (9b), (9c), (9d), (9e), (9f), (9g), (9h) and (9i), when u is greater than 0, the substituents R are in each case the same or different and are preferably selected from the group consisting of D, F, an alkyl group having 1 to 10 carbon atoms, or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, and one or more R 1 In this R, the aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms is preferably derived from benzene, dibenzofuran, dibenzothiophene, 9-phenylcarbazole, biphenyl and terphenyl, which may be substituted by one or more R 1 The substituent(s) [R] may be substituted by a radical. u Preferred positions of are 1, 2, 3 or 4, or 1 and 4, and 1 and 3, more preferably a combination of 1 and 3, 2 or 3, most preferably 3, R has one of the preferred definitions above, and u is greater than 0. [R] u Particularly preferred substituents R in are carbazol-9-yl, biphenyl, terphenyl and dibenzofuranyl.

[0164] In the compounds of formulae (9), (9a), (9b), (9c), (9d), (9e), (9f), (9g), (9h) and (9i), v is preferably 0, 1 or 2 and R has the above or following definitions. More preferably, v=0 or 1, most preferably 0.

[0165] In the compounds of formulae (9), (9a), (9b), (9c), (9d), (9e), (9f), (9g), (9h) and (9i), when v is greater than 0, the substituents R are in each case the same or different and are preferably selected from the group consisting of D, F, an alkyl group having 1 to 10 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, a linear or branched alkyl group having 1 to 4 carbon atoms or CN. It is possible here for two or more adjacent R substituents to join together to form a monocyclic or polycyclic ring system. In this R, the aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms is preferably derived from benzene, dibenzofuran, dibenzothiophene, 9-phenylcarbazole, biphenyl, terphenyl and triphenylene.

[0166] Substituent(s) [R] v is position 1, 2 or 3, more preferably position 3, R has one of the preferred definitions above, and v is greater than 0.

[0167] Ar' in N(Ar')2 is one or more substituents R 1 Preferably, Ar' is derived from benzene, dibenzofuran, fluorene, spirobifluorene, dibenzothiophene, 9-phenylcarbazole, biphenyl and terphenyl, optionally substituted by: wherein Ar' is preferably unsubstituted.

[0168] Preferred substituents R and R 1 are the same as those already detailed above as being preferred for compounds of formula (1).

[0169] In the compounds of formulas (9), (9a), (9b), (9c), (9d), (9e), (9f), (9g), (9h) and (9i) above, Ar 4is, independently in each occurrence, an aromatic ring system having 6 to 30 aromatic ring atoms, or a heteroaromatic ring system having 10 to 30 aromatic ring atoms, which is optionally joined by one or more R 1 It may be substituted by a radical. 4 are preferably derived from benzene, dibenzofuran, fluorene, spirobifluorene, dibenzothiophene, 9-phenylcarbazole, biphenyl and terphenyl, which may be substituted with one or more substituents R 1 and R 1 has the definition given above.

[0170] having 10 to 40 carbon atoms and one or more substituents R 1 In the case of heteroaromatic ring systems, which may be substituted by, electron-rich ring systems are particularly preferred, where R 1 The substituted ring system preferably contains exactly one nitrogen atom throughout its entirety, or optionally, R 1 Substituted ring systems contain, throughout, one or more oxygen and / or sulfur atoms.

[0171] In the compounds of formulae (9), (9a), (9b), (9c), (9d), (9e), (9f), (9g), (9h) and (9i), Ar′ and Ar 4 is independently, in each occurrence, preferably selected from the same groups listed above for structures R-1 through R-81.

[0172] Examples of suitable compounds of formula (9), (9a), (9b), (9c), (9d), (9e), (9f), (9g), (9h) and (9i) are the structures depicted in the table below.

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[0198] In particular, suitable examples of compounds of formulae (9), (9a), (9b), (9c), (9d), (9e), (9f), (9g), (9h) and (9i) selected according to the present invention are compounds H1 to H27 as illustrated below:

[0199] [ka]

[0200] [ka]

[0201] [ka]

[0202] [ka]

[0203] Additionally, the compounds of the present invention can be used in a hole blocking layer and / or an electron transport layer.

[0204] In the further layer of the organic electroluminescent device of the present invention, it is possible to use any material that is usually used according to the prior art.Therefore, those skilled in the art can use any material that is known in organic electroluminescent devices in combination with the compound of the present invention according to formula (1) or preferred embodiment without using the technology of the present invention.

[0205] Further preferred is an organic electroluminescent device, characterized in that one or more layers are applied by a sublimation process. In this case, the material is applied in a vacuum sublimation system at 10 -5 Less than mbar, preferably less than 10 -6 The deposition is carried out at an initial pressure of less than 10 mbar. -7 It is also possible to go below mbar.

[0206] Likewise preferred are organic electroluminescent devices, characterized in that one or more layers are applied by the OVPD (organic vapor phase deposition) method or with the aid of carrier gas sublimation. In this case, the materials are preferably 10 -5 It is applied at pressures between mbar and 1 bar. A special case of this method is the OVJP (Organic Vapor Jet Printing) method, in which the material is applied directly by a nozzle and thus structured (e.g., MS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).

[0207] Further, organic electroluminescent devices are selected, characterized in that one or more layers are produced from solution, for example by spin-coating or by any printing method, such as inkjet printing, LITI (light-induced thermal imaging, thermal transfer printing), screen printing, flexographic printing, offset printing or nozzle printing. For this, soluble compounds are required, which can be obtained, for example, by suitable substitution.

[0208] In addition, hybrid methods are possible, for example where one or more layers are applied from solution and one or more further layers are applied by vapor deposition. For example, it is possible to apply an emissive layer from solution and an electron transport layer by vapor deposition.

[0209] These methods are generally known to those skilled in the art and can be applied by those skilled in the art to organic electroluminescent devices containing the compounds of the present invention without using the techniques of the present invention.

[0210] The compounds of the present invention generally have very good properties for use in organic electroluminescent devices.In particular, when the compounds of the present invention are used in organic electroluminescent devices, the lifetime is better than that of similar compounds according to the prior art.At the same time, the further properties of organic electroluminescent devices, especially efficiency and voltage, are comparable or even superior.

[0211] The present invention will now be illustrated in detail by the examples that follow, without any intention of limiting the invention thereby.

[0212] [example] The following syntheses are carried out under a protective gas atmosphere in dry solvents unless otherwise specified. Solvents and reagents can be purchased, for example, from Sigma-ALDRICH or ABCR. The respective numbers in square brackets or quoted for individual compounds relate to the CAS numbers of compounds known from the literature. Preparation of synthons: S1:

[0213] [ka]

[0214] 2-(8-chlorodibenzofuran-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [2140871-51-6] (32.86 g, 100.0 mmol), 2-chloro-4-dibenzofuran-3-yl-6-phenyl-1,3,5-triazine [2142681-84-1] (37.57 g, 105.0 mmol) and sodium carbonate (22.26 g, 210.0 mmol) are suspended in 600 ml of ethylene glycol dimethyl ether and 300 ml of water and inactivated for 30 minutes. Subsequently, tri-o-tolylphosphine (913 mg, 3.0 mmol) is added, followed by palladium(II) acetate (112 mg, 0.5 mmol) and the reaction mixture is heated under reflux for 20 hours. After cooling, the precipitated solid is suction filtered and washed with ethanol. The crude product was recrystallized from m-xylene. Yield: 46.11 g (88 mmol, 88%) solid, 98% by HPLC.

[0215] In a similar manner, the following compounds can be prepared: Purification can be performed using column chromatography or recrystallization can be performed using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-dioxane, dimethylsulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.

[0216] [ka]

[0217] [ka]

[0218] S50:

[0219] [ka]

[0220] An initial charge of S1 (46.11 g, 88.0 mmol), bis(pinacolato)diboron[73183-34-3] (25.39 g, 100.0 mmol) and potassium acetate (28.82 g, 293.6 mmol) in 1,4-dioxane (700 ml) is inerted with argon for 2 min. Subsequently, XPhos[564483-18-7] (456 mg, 0.96 mmol) and Pd2(dba)3[51364-51-3] (435 mg, 0.48 mmol) are added and the reaction mixture is stirred at reflux for 26 h. After cooling, the solvent is removed by rotary evaporation and the residue is worked up by extraction with toluene / water. The organic phase is dried over Na2SO4 and concentrated to dryness by rotary evaporation. The residue is boiled under reflux for 2 hours with ethyl acetate, the solid is suction filtered and washed with ethyl acetate. Yield: 49.4 g (80.2 mmol, 91%) of solid; 1 97% by H NMR.

[0221] In a similar manner, the following compounds can be prepared: Purification can be performed using column chromatography or recrystallization can be performed using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-dioxane, dimethylsulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.

[0222] [ka]

[0223] [ka]

[0224] S100:

[0225] [ka]

[0226] Under an inert atmosphere, 6-bromo-1-chlorodibenzofuran [2144800-21-3] (28.15 g, 100 mmol), 8H-[1]benzothieno-[2,3-c]carbazole [1255309-17-1] (28.70 g, 105 mmol) and sodium tert-butoxide (19.21 g, 200 mmol) were first charged in 1000 ml of ortho-xylene, followed by tri-tert-butylphosphine [13716-12-6] (1 mol / l solution in toluene, 5.0 ml, 5.0 mmol) and tris(dibenzylideneacetone)dipalladium [51364-51-3] (1.14 g, 1.25 mmol) in sequence, and the reaction mixture was heated under reflux for 16 hours. The reaction mixture is cooled to room temperature and worked up by extraction with toluene / water. The combined organic phases are dried over Na2SO4 and the solvent is removed under reduced pressure on a rotary evaporator. The solid obtained is suspended in 300 ml of ethanol, stirred at reflux for 1 hour and suction filtered. The crude product is recrystallized from ethyl acetate. Yield: 32.2 g (68 mmol, 68%) of a solid. 1 97% by H NMR.

[0227] In a similar manner, the following compounds can be prepared: Purification can be performed using column chromatography or recrystallization can be performed using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-dioxane, dimethylsulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.

[0228] [ka]

[0229] S150:

[0230] [ka]

[0231] Under an inert atmosphere, an initial charge of 1-bromo-8-iododibenzofuran [1822311-11-4] (37.28 g, 100 mmol), 3-phenyl-9H-carbazole [103012-26-6] (16.71 g, 100 mmol), potassium carbonate (34.55 g, 250 mmol), copper iodide (3.81 g, 20.0 mmol) and 1,3-di(2-pyridinyl)propane-1,3-dione (4.52 g, 20.0 mmol) in DMF (350 ml) is inerted with argon for an additional 15 min and then stirred at 115° C. for 32 h. The mixture is allowed to cool to room temperature, filtered through a bed of Celite, rinsed twice with 200 ml DMF and the filtrate concentrated to dryness on a rotary evaporator. The residue is worked up by extraction with dichloromethane / water, the organic phase is washed twice with water and once with saturated NaCl solution and dried over Na2SO4. 150 ml of ethanol are added, the dichloromethane is removed in a rotary evaporator down to 500 mbar, the precipitated solid is suction filtered and washed with ethanol. Yield: 24.71 g (50.6 mmol, 51%) of a grey solid; 1 95% by H NMR.

[0232] In a similar manner, the following compounds can be prepared: Purification can be performed using column chromatography or recrystallization can be performed using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-dioxane, dimethylsulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.

[0233] [ka]

[0234] [ka]

[0235] [ka]

[0236] S200:

[0237] [ka]

[0238] To the initial charge of 8-bromodibenzofuran-1-yl trifluoromethanesulfonate [2247123-46-0] (47.00 g, 118.9 mmol), 4,4,5,5-tetramethyl-2-(2-triphenylenyl)-1,3,2-dioxaborolane (49.72 g, 140.4 mmol) and K2CO3 (32.88 g, 237.9 mmol) in a flask, toluene (500 ml) and water (150 ml) are added and the mixture is inerted with argon for 30 min. Subsequently, Pd2(dba)3 (545 mg, 0.59 mmol) and tri-ortho-tolylphosphine [6163-58-2] (724 mg, 2.38 mmol) are added and the mixture is heated under reflux for 24 h. After cooling, the precipitated solid is suction filtered and washed twice with ethanol. The crude product is extracted by stirring under reflux in ethanol for 2 hours, and the solid is cooled and then filtered off with suction. Yield: 58.8 g (108 mmol, 91%) of solid; purity: 1 98% by H NMR.

[0239] In a similar manner, the following compounds can be prepared: Purification can be performed using column chromatography or recrystallization can be performed using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-dioxane, dimethylsulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.

[0240] [ka]

[0241] [ka]

[0242] Preparation of the Compounds of the Invention: Synthesis of P1:

[0243] [ka]

[0244] To an initial charge of 2,4-diphenyl-6-[8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-dibenzofuranyl]-1,3,5-triazine [2138490-96-5] (15.31 g, 29.1 mmol), S200 (15.06 g, 27.8 mmol) and K3PO4 (12.17 g, 57.3 mmol) in a flask, tetrahydrofuran (200 ml) and water (50 ml) are added and the mixture is inerted with argon for 30 minutes. Subsequently, Pd(OAc)2 (124 mg, 0.55 mmol) and XPhos [564483-18-7] (556 mg, 1.11 mmol) are added and the mixture is heated under reflux for 24 hours. After cooling, the precipitated solid is filtered off with suction and washed twice with water and twice with ethanol. The crude product is subjected to hot extraction three times with toluene / heptane (1:1), then recrystallized three times from toluene and finally sublimed under high vacuum. Yield: 14.8 g (18.7 mmol, 67%); Purity: >99.9% by HPLC. In a similar manner, the following compounds can be prepared. The catalytic system (palladium source and ligand) used here can be Pd2(dba)3 with SPhos [657408-07-6] or bis(triphenylphosphine)palladium(II) chloride [13965-03-2]. Purification can also be performed using column chromatography, or recrystallization or hot extraction using other standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-dioxane, or recrystallization using high boiling substances such as dimethylsulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.

[0245] [ka]

[0246] [ka]

[0247]

change

[0248]

change

[0249]

change

[0250]

change

[0251]

change

[0252]

change

[0253] P100:

[0254]

change

[0255] To the initial charge of 2,4-diphenyl-6-[8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-dibenzofuranyl]-1,3,5-triazine [2138490-96-5] (15.31 g, 29.1 mmol), S150 (14.41 g, 29.5 mmol) and Na2CO3 (6.17 g, 58.2 mmol) in a flask, toluene (300 ml) and water (100 ml) are added and the mixture is inerted with argon for 30 minutes. Tetrakis(triphenylphosphine)palladium(0) [14221-01-3] (1.00 g, 0.87 mmol) is then added and the mixture is heated under reflux for 36 hours. After cooling, the reaction mixture is worked up by extraction with toluene and water, the combined organic phases are dried over Na2SO4 and the filtrate is concentrated to dryness by rotary evaporation. The residue is suspended in 350 ml of hot EtOH and stirred at reflux for 1 h, after cooling the solid is suction filtered. The crude product is subjected to two hot extractions with toluene / heptane (1:1), then recrystallized three times from n-butyl acetate and finally sublimed under high vacuum. Yield: 14.8 g (18.7 mmol, 67%); purity: >99.9% by HPLC. In a similar manner, the following compounds can be prepared. The catalyst system used here can be Pd2(dba)3 (palladium source and ligand) using SPhos [657408-07-6] or bis(triphenylphosphine)palladium(II) chloride [13965-03-2] rather than tetrakis(triphenylphosphine)palladium(0). Purification can also be performed using column chromatography, or recrystallization or hot extraction using other standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-dioxane, or recrystallization using high boiling materials such as dimethylsulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.

[0256] [ka]

[0257] [ka]

[0258] [ka]

[0259] Device Examples Pretreatment of Examples V1-V5, E1-E28 and B1-B54 Glass plaques coated with 50 nm thick structured ITO (indium tin oxide) are treated first with oxygen plasma and then with argon plasma prior to coating. These plasma-treated glass plaques form the substrates on which the OLEDs are applied.

[0260] The OLED basically has the following layer structure: substrate / hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / emissive layer (EML) / optional hole blocking layer (HBL) / electron transport layer (ETL) / optional electron injection layer (EIL) and finally a cathode. The cathode is formed by a 100 nm thick layer of aluminum. The exact structure of the OLED can be found in Table 1. The materials required to produce the OLED are shown in Table 3. The data of the OLED is listed in Table 2.

[0261] All materials are applied by thermal evaporation in a vacuum chamber. In this case, the emissive layer always consists of at least one matrix material (host material) and a luminescent dopant (emitter) that is added to the matrix material(s) in a certain volumetric proportion by co-evaporation. Here, a specification given in the form IV1:H4:TEG2 (44%:44%:12%) means that the materials IV1 and 42 are present in the layer in a volumetric proportion of 44% and TEG1 in a volumetric proportion of 12%, respectively. Similarly, the electron transport layer may also consist of a mixture of two materials.

[0262] OLEDs are characterized by standard methods. For this, the electroluminescence spectrum, current efficiency (CE, measured in cd / A) and external quantum efficiency (EQE, measured in %) as well as the lifetime are determined as a function of luminance calculated from the current-voltage-luminance characteristic assuming Lambertian emission characteristics. Electroluminescence spectra are measured at 1000 cd / m 2 From this, calculate the CIE1931 x and y color coordinates. The parameter U1000 in Table 2 is 1000 cd / m 2 CE1000 and EQE1000 refer to the voltage required for a brightness of 1000cd / m 2 The parameter U10 in Table 2 means the current efficiency and external quantum efficiency obtained at 10 mA / cm 2 CE10 and EQE10 refer to the voltage required for a current density of 10mA / m 2 The current efficiency and external quantum efficiency obtained by

[0263] The lifetime LT is defined as the time until the luminance drops to a certain percentage L1 from the starting luminance during operation at a constant current density j0. The number L1=80% in Table 2 means that the lifetime reported in the LT column corresponds to the time after the luminance has dropped to 80% of its starting value. Use of the Materials of the Invention in the Emitting Layer of Phosphorescent OLEDs The inventive materials IV1-IV31 are used in examples E1-E28 and B1-B54 as matrix materials in the emissive layer of green phosphorescent OLEDs. With otherwise comparable performance data of the OLEDs, the use of the inventive compounds achieves a clearly longer lifetime compared to PA1 (see Table 2). E1-E3 can now be compared directly with V1, E4-E7 directly with V2, E8-E12 directly with V3, E13-E17 directly with V4, and E18-E28 directly with V5, each comparison showing an improvement in lifetime over PA1.

[0264] [Table 1-1]

[0265]

Table 1-2

[0266]

Table 1-3

[0267]

Table 1-4

[0268]

Table 1-5

[0269]

Table 1-6

[0270]

Table 1-7

[0271]

Table 2-1

[0272]

Table 2-2

[0273]

Table 2-3

[0274]

Table 3-1

[0275]

Table 3-2

[0276]

Table 3-3

[0277]

Table 3-4

[0278]

Table 3-5

[0279]

Table 3-6

[0280]

Table 3-7

[0281]

Table 3-8

Claims

1. Compound of formula (1) 【Chemistry 1】 (wherein the symbols used are as follows: Y is O or S; Z, at each occurrence, is the same or different, and is CR or N, with the proviso that at least two Z are N; Ar １ are in each case the same or different and are an aromatic ring system having 6 to 40 aromatic ring atoms which may be substituted by one or more R radicals, or a heteroaromatic ring system having 5 to 40 aromatic ring atoms which is linked to the dibenzofuran or dibenzothiophene via a nitrogen atom and which may be substituted by one or more R radicals, or a dibenzofuran or dibenzothiophene group which may be substituted by one or more R radicals; Ar ２ is the same or different in each occurrence and is an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, optionally substituted by one or more R radicals; R is the same or different in each occurrence and is H, D, F, Cl, Br, I, N(Ar'), ２ , N(R １ ) ２ ,OAr',SAr',CN,NO ２ , OR １ , S.R. １ , COOR １ , C(=O)N(R １ ) ２ , Si(R １ ) ３ , B(OR １ ) ２ , C(=O)R １ , P(=O)(R １ ) ２ , S(=O)R １ , S(=O) ２ R １ , OSO ２ R １ , a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, wherein said alkyl, alkenyl or alkynyl group is in each case represented by one or more R １ radicals) (wherein one or more non-adjacent CH ２ The group is Si(R １ ) ２ , C=O, NR １ , O, S or CONR １ or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, in each case one or more R １ at the same time, the two R radicals may also together form a ring system; Ar′, in each occurrence, is the same or different, and is an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms; １ At the same time, two Ar′ radicals attached to the same nitrogen atom may also be substituted by a single bond or N(R １ ), C(R １ ) ２ , optionally cross-linked to each other by bridges selected from O and S; R １ are the same or different in each case and are H, D, F, Cl, Br, I, N(R ２ ) ２ , C.N., N.O. ２ , OR ２ , S.R. ２ , Si(R ２ ) ３ , B(OR ２ ) ２ , C(=O)R ２ , P(=O)(R ２ ) ２ , S(=O)R ２ , S(=O) ２ R ２ , OSO ２ R ２ , a linear alkyl group having 1 to 20 carbon atoms, or an alkenyl or alkynyl group having 2 to 20 carbon atoms, or a branched or cyclic alkyl group having 3 to 20 carbon atoms, wherein said alkyl, alkenyl or alkynyl group each comprises one or more R ２ radicals) (wherein one or more non-adjacent CH ２ The group is Si(R ２ ) ２ , C=O, NR ２ , O, S or CONR ２ and one or more hydrogen atoms in said alkyl, alkenyl or alkynyl group may be replaced by D, F, Cl, Br, I or CN), or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, in each case one or more R ２ At the same time, two or more R １ the radicals together may form an aliphatic ring system; R ２ is in each occurrence the same or different and is H, D, F, CN, or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 carbon atoms, especially a hydrocarbyl radical, in which one or more hydrogen atoms may also be replaced by F; p, q, in each occurrence, are the same or different and are 0, 1, 2 or 3; r is 0, 1, 2, 3, or 4, with the proviso that r is equal to or less than (4-j); s is 0, 1, 2, or 3, with the proviso that s is equal to or less than (3−k); j, k are the same or different in each occurrence and are 0, 1, 2 or 3, with the proviso that j+k≧1).

2. 2. The compound of claim 1, characterized in that all three Z groups are N or two Z groups are N and the third Z group is CH.

3. Compound of formula (4) 【Chemistry 2】 (wherein the symbols and indices used have the definitions given in claim 1 ) 3. The compound according to claim 1 or 2, selected from:

4. Compound of formula (5) 【Chemistry 3】 (wherein the symbols and indices used have the definitions given in claim 1 ) The compound according to any one of claims 1 to 3, selected from

5. Compounds of formula (6a) and (6b) 【Chemistry 4】 (wherein the symbols and subscripts used have the definitions given above) The compound according to any one of claims 1 to 4, selected from

6. Compounds of formula (7a) and (7b) 【Chemistry 5】 (wherein the symbols used have the definitions given in claim 1) The compound according to any one of claims 1 to 5, selected from

7. When j=1, the Ar １ The Ar group is attached to the dibenzofuran or dibenzothiophene at the 7- or 8-position, and when k=1, the Ar １ 7. The compound according to claim 1, wherein a group is attached at the 3- or 4-position of the dibenzofuran or dibenzothiophene.

8. Ar ２ Compounds according to any one of claims 1 to 7, characterized in that, are in each case the same or different, denote an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, optionally substituted by one or more non-aromatic R radicals.

9. Ar １ is an aromatic ring system having 6 to 30 aromatic ring atoms, optionally substituted by one or more non-aromatic R radicals, or N-carbazolyl optionally substituted by one or more R radicals, or dibenzofuran or dibenzothiophene, each optionally substituted by one or more R radicals.

10. A formulation comprising at least one compound according to any one of claims 1 to 9 and at least one further compound and / or solvent.

11. Use of a compound according to any one of claims 1 to 9 in an electronic device.

12. An electronic device comprising at least one compound according to any one of claims 1 to 9.

13. 13. The electronic device according to claim 12, which is an organic electroluminescent device, characterized in that the compound according to any one of claims 1 to 9 is used as a matrix material for a phosphorescent emitter in an emitting layer.

14. The compound according to any one of claims 1 to 9 is used in combination with a further matrix material, said further matrix material being a compound of formula (9) 【Chemistry 6】 (In the formula, R, R １ , R ２ and Ar′ have the definitions detailed in claim 1, with further symbols and subscripts used being as follows: R Ａ is H, -L ３ -Ar ５ Or -L １ -N(Ar') ２ and R Ｂ is Ar ４ Or -L ２ -N(Ar') ２ and L １ , L ２ are the same or different in each occurrence and are a single bond or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, and one or more R １ may be substituted with a radical; L ３ is a single bond or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, and one or more R ２ may be substituted by a radical, where one substituent R １ may form a ring with the substituent R on the carbazole; Ar ４ is an aromatic ring system having 6 to 40 aromatic ring atoms, or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be represented by one or more R １ may be substituted with a radical; Ar ５ are the same or different in each occurrence and are unsubstituted or substituted 9-arylcarbazolyl or unsubstituted or substituted carbazol-9-yl, which are represented by one or more R １ radical, where one or more of the two R １ Each radical is or one R １ The radicals may independently form, together with one R radical, a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring, where aryl is an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms and R １ may be substituted with; u, independently at each occurrence, is 0, 1, 2, or 3; v, at each occurrence, is independently 0, 1, 2, 3, or 4.

14. The electronic device according to claim 13,

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