Cyclic compounds for organic electroluminescent devices

Abstract

The present invention relates to cyclic compounds suitable for use in electronic devices, and to electronic devices, in particular organic electroluminescent devices, containing said compounds.

Description

[0001] The present invention relates to cyclic compounds for use in electronic devices, especially in organic electroluminescent devices, and electronic devices, especially organic electroluminescent devices, comprising these materials.

[0002] The luminescent material used in organic electroluminescent devices is usually a phosphorescent organometallic complex. For reasons of quantum mechanics, the use of organometallic compounds as phosphorescent emitters can achieve up to four times the energy efficiency and power efficiency. In electroluminescent devices, especially in electroluminescent devices that also exhibit triplet luminescence (phosphorescence), there is still a need for improvement. The properties of phosphorescent electroluminescent devices do not only depend on the triplet emitters used. More particularly, other materials such as matrix materials used are also particularly important here. Therefore, the improvement of these materials can also cause a significant improvement in the performance of electroluminescent devices.

[0003] The electroluminescent device described in detail above is the subject matter of the document WO 2014 / 015938 A1.

[0004] In general, when these materials are used, for example, as matrix materials, there is still a need for improvement, in particular with regard to the lifetime of the components and with regard to efficiency and operating voltage.

[0005] It was therefore an object of the present invention to provide a compound which is suitable for use in organic electronic devices, in particular organic electroluminescent devices, and which, when used in such devices, leads to good device properties, and to provide corresponding electronic devices.

[0006] More particularly, an object solved by the present invention is to provide compounds which lead to a high lifetime, good efficiency and a low operating voltage.In particular the nature of the matrix material also has a significant influence on the lifetime and efficiency of an organic electroluminescent device.

[0007] Another object of the present invention is to provide a compound characterized by a low refractive index (RI).

[0008] Another object of the present invention can be considered to be to provide compounds suitable for use in phosphorescent or fluorescent electroluminescent devices, in particular as host materials. A particular problem solved by the present invention is to provide host materials, which are suitable for red phosphorescent and yellow phosphorescent electroluminescent devices, in particular for red phosphorescent electroluminescent devices, and, if appropriate, also for blue phosphorescent electroluminescent devices.

[0009] Furthermore, the compounds, in particular when they are employed as matrix materials, as hole-transport materials or as electron-blocking materials in organic electroluminescent devices, should give rise to devices having excellent color purity.

[0010] Another object can be considered to be to provide very cheap and stable quality electronic devices with excellent performance.

[0011] Furthermore, it should be possible to use or modify the electronic device for many purposes. More particularly, the performance of the electronic device should be maintained over a wide temperature range.

[0012] It has been surprisingly found that this object is achieved by specific compounds, which are described in detail later, which are very suitable for use in electroluminescent devices and cause organic electroluminescent devices to show good properties, especially in terms of lifetime, color purity, efficiency, operating voltage and refractive index. Therefore, the present invention provides these compounds and electronic devices, especially organic electroluminescent devices, comprising these compounds.

[0013] The present invention provides a compound comprising at least one structure of formula (I), preferably a compound of formula (I),

[0014]

[0015] The symbols are as follows:

[0016] Z a are in each case identical or different and are Ar a 、N(Ar c ) 2 or (Ar)N(Ar c ) 2 ;

[0017] Z b are in each case identical or different and are Ar b 、N(Ar d ) 2 or (Ar)N(Ar d ) 2 ;

[0018] R a are in each case identical or different and are straight-chain alkyl, alkoxy or thioalkoxy radicals having 1 to 10 carbon atoms or branched or cyclic alkyl, alkoxy or thioalkoxy radicals having 3 to 10 carbon atoms, each of which may be replaced by one or more R 2 The group is preferably a linear alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, each of which may be substituted by one or more R 2 At the same time, two or more preferably adjacent substituents R a Together they can form a ring system;

[0019] R bare in each case identical or different and are straight-chain alkyl, alkoxy or thioalkoxy radicals having 1 to 10 carbon atoms or branched or cyclic alkyl, alkoxy or thioalkoxy radicals having 3 to 10 carbon atoms, each of which may be replaced by one or more R 2 The group is preferably a linear alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, each of which may be substituted by one or more R 2 Group substitution; at the same time, two adjacent substituents R b Together they can form a ring system;

[0020] R c are in each case identical or different and are H, D, a linear alkyl, alkoxy or thioalkoxy group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 10 carbon atoms, each of which may be replaced by one or more R 2 A group is substituted, preferably H, D, a linear alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, each of which may be substituted by one or more R 2 The group is substituted, preferably H, D, a straight-chain alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably H, D;

[0021] Ar a ,Ar b ,Ar c ,Ar d are identical or different in each case and are an aromatic or heteroaromatic ring system having 6 to 60 aromatic ring atoms and which may be substituted by one or more R groups; at the same time, two Ar groups bonded to the same nitrogen atom c ,Ar d The groups may also be bridged to each other via a single bond or a bridging group selected from the following groups: B(R), C(R) 2 、Si(R) 2 、C=O、C=NR、C=C(R) 2 ,RC=CR,O,S,S=O,SO 2 , N(R), P(R), P(=O)R and an ortho-linked phenylene group which may be substituted with one or more R groups, the bridging group preferably being selected from: C(R) 2 , O, N(R) and an ortho-linked phenylene group which may be substituted with one or more R groups; preferably, Ar a ,Ar b ,Ar c ,Ar dare identical or different in each case and are aryl or heteroaryl radicals having 6 to 40 aromatic ring atoms and which may be substituted by one or more R radicals; at the same time, two Ar, Ar c ,Ar d The groups may also be bridged to each other via a single bond or a bridging group selected from the following groups: B(R), C(R) 2 、Si(R) 2 、C=O、C=NR、C=C(R) 2 ,RC=CR,O,S,S=O,SO 2 , N(R), P(R), P(=O)R and an ortho-linked phenylene group which may be substituted with one or more R groups, the bridging group preferably being selected from: C(R) 2 , O, N(R), and an ortho-linked phenylene group which may be substituted with one or more R groups;

[0022] Ar is identical or different in each case and is a linked aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and which may be substituted by one or more R groups; at the same time, one Ar group and one Ar group bonded to the same nitrogen atom c ,Ar d One or both of the groups may also be bridged to each other via a single bond or a bridging group selected from the following groups: B(R), C(R) 2 、Si(R) 2 、C=O、C=NR、C=C(R) 2 ,RC=CR,O,S,S=O,SO 2 , N(R), P(R), P(=O)R and an ortho-linked phenylene group which may be substituted with one or more R groups, the bridging group preferably being selected from: C(R) 2 , O, N(R) and an ortho-attached phenylene group which may be substituted by one or more R groups; preferably, Ar is identical or different in each case and is an arylene or heteroarylene group having 5 to 40 aromatic ring atoms and which may be substituted by one or more R groups; at the same time, one Ar group and an Ar bonded to the same nitrogen atom c ,Ar d One or both of the groups may also be bridged to each other via a single bond or a bridging group selected from the following groups: B(R), C(R) 2 、Si(R) 2 、C=O、C=NR、C=C(R) 2 ,RC=CR,O,S,S=O,SO 2 , N(R), P(R), P(=O)R and an ortho-linked phenylene group which may be substituted with one or more R groups, the bridging group preferably being selected from: C(R)2 , O, N(R), and an ortho-linked phenylene group which may be substituted with one or more R groups;

[0023] R is in each case identical or different and is H, D, OH, F, Cl, Br, I, CN, NO 2 ,N(Ar') 2 ,N(R 1 ) 2 ,C(=O)N(Ar') 2 ,C(=O)N(R 1 ) 2 ,C(Ar') 3 , C(R 1 ) 3 ,Si(Ar') 3 ,Si(R 1 ) 3 ,B(Ar') 2 , B(R 1 ) 2 , C(=O)Ar', C(=O)R 1 , P(=O)(Ar') 2 , P(=O)(R 1 ) 2 ,P(Ar') 2 , P(R 1 ) 2 ,S(=O)Ar',S(=O)R 1 ,S(=O) 2 Ar', S(=O) 2 R 1 , OSO 2 Ar', OSO 2 R 1 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, wherein the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may in each case be replaced by one or more R 1 group substitution, where one or more non-adjacent CH 2 The group can be R 1 C=CR 1 、C≡C、Si(R 1 ) 2 , C=O, C=S, C=Se, C=NR 1 、-C(=O)O-、-C(=O)NR 1 -、NR 1 ,P(=O)(R 1), -O-, -S-, SO or SO 2 or having 5 to 60 aromatic ring atoms and in each case being replaced by one or more R 1 An aromatic or heteroaromatic ring system substituted with a radical, or having 5 to 60 aromatic ring atoms and substituted by one or more R 1 At the same time, the two R groups can also form a ring system together or with other groups;

[0024] Ar' is identical or different in each case and is a ring having 5 to 60 aromatic ring atoms and may be replaced by one or more R 1 At the same time, two Ar' groups bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom may also be bridged to each other by a single bond or a bridging group selected from the following groups: B(R 1 )、C(R 1 ) 2 、Si(R 1 ) 2 、C=O、C=NR 1 , C=C(R 1 ) 2 ,O,S,S=O,SO 2 、N(R 1 )、P(R 1 ) and P(=O)R 1 ;

[0025] R 1 are in each case identical or different and are H, D, F, Cl, Br, I, CN, NO 2 ,N(Ar”) 2 ,N(R 2 ) 2 ,C(=O)Ar”,C(=O)R 2 , P(=O)(Ar”) 2 , P(Ar”) 2 , B(Ar”) 2 , B(R 2 ) 2 ,C(Ar”) 3 , C(R 2 ) 3 , Si(Ar”) 3 ,Si(R 2 ) 3 , a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R 2group substitution, where one or more non-adjacent CH 2 The group can be -R 2 C=CR 2 -、-C≡C-、Si(R 2 ) 2 ,C=O,C=S,C=Se,C=NR 2 、-C(=O)O-、-C(=O)NR 2 -、NR 2 ,P(=O)(R 2 ), -O-, -S-, SO or SO 2 and one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be replaced by one or more R 2 or having 5 to 60 aromatic ring atoms and may be substituted with one or more R 2 substituted aryloxy or heteroaryloxy groups, or having 5 to 60 aromatic ring atoms and may be replaced by one or more R 2 substituted aralkyl or heteroaralkyl groups, or combinations of these systems; at the same time, two or more preferably adjacent R 1 The groups together can form a ring system; at the same time, one or more R 1 The group may form a ring system with the rest of the compound;

[0026] Ar" is identical or different in each case and is a radical having 5 to 30 aromatic ring atoms and may be replaced by one or more R 2 At the same time, two Ar" groups bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom may also be bridged to each other by a single bond or a bridging group selected from the following groups: B(R 2 )、C(R 2 ) 2 、Si(R 2 ) 2 、C=O、C=NR 2 , C=C(R 2 ) 2 ,O,S,S=O,SO 2 、N(R 2 )、P(R 2 ) and P(=O)R 2 ;

[0027] R 2are in each case identical or different and are selected from H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms and in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN, and which may be substituted by one or more alkyl radicals each having 1 to 4 carbon atoms; at the same time, two or more preferably adjacent substituents R 2 Together they can form a ring system;

[0028] Where Z a and Z b The groups do not form a ring system.

[0029] Z a and Z b The groups do not form a ring system. This means that the two groups are connected to each other only via the basic structure shown in formula (I), but not via the rings used to define Z a and Z b Ar, Ar a ,Ar b ,Ar c ,Ar d These include R, R 1 and R 2 group, through the R, R 1 and R 2 The group can replace Ar, Ar a ,Ar b ,Ar c ,Ar d Group.

[0030] It is also possible that the compound is a and Z b The group is symmetrical.

[0031] Another possible situation is that the compound relative to Z a and Z b The group is asymmetric.

[0032] Aryl groups in the context of the present invention contain 6 to 40 carbon atoms; heteroaryl groups in the context of the present invention contain 3 to 40 carbon atoms and at least one heteroatom, provided that the sum of carbon atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O and / or S. Here, aryl groups or heteroaryl groups are understood to mean simple aromatic rings, i.e. benzene, or simple heteroaromatic rings such as pyridine, pyrimidine, thiophene, etc., or fused (annulated) aryl or heteroaryl groups such as naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc. In contrast, aromatic compounds which are linked to one another by single bonds, such as biphenyl, are not referred to as aryl or heteroaryl groups, but as aromatic ring systems.

[0033] The electron-deficient heteroaryl group in the context of the present invention is a heteroaryl group with at least one heteroaromatic six-membered ring, and the heteroaromatic six-membered ring has at least one nitrogen-atom. Other aromatic or heteroaromatic five-membered rings or six-membered rings can be fused to the six-membered ring. The example of the electron-deficient heteroaryl group is pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinazoline or quinoxaline.

[0034] In the context of the present invention, an aromatic ring system contains 6 to 60 carbon atoms in the ring system. In the context of the present invention, a heteroaromatic ring system contains 3 to 60 carbon atoms and at least one heteroatom in the ring system, provided that the sum of carbon atoms and heteroatoms is at least 5. The heteroatom is preferably selected from N, O and / or S. In the context of the present invention, an aromatic or heteroaromatic ring system is understood to refer to a system in which it does not necessarily contain only aryl or heteroaryl groups, but in which two or more aryl or heteroaryl groups can also be connected by non-aromatic units, such as carbon, nitrogen or oxygen atoms. For example, in the context of the present invention, systems such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc. should also be regarded as aromatic ring systems, and the same is true for systems in which two or more aryl groups are connected, for example, by short alkyl groups. Preferably, the aromatic ring system is selected from fluorene, 9,9′-spirobifluorene, 9,9-diarylamine or a group in which two or more aryl and / or heteroaryl groups are linked to each other via a single bond.

[0035] In the context of the present invention, a carbon atom may contain 1 to 20 carbon atoms and wherein individual hydrogen atoms or CH 2Aliphatic hydrocarbon radicals or alkyl radicals or alkenyl or alkynyl radicals which may also be substituted by the abovementioned radicals are preferably understood as meaning methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl radicals. Alkoxy groups having 1 to 40 carbon atoms are preferably understood to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy. Thioalkyl radicals having 1 to 40 carbon atoms are to be understood as meaning in particular methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, n-pentylthio, sec-pentylthio, n-hexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, vinylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, cyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthio, cyclooctenylthio, ethynylthio, propynylthio, butynylthio, pentynylthio, hexynylthio, heptynylthio or octynylthio. Generally, the alkyl, alkoxy or thioalkyl groups according to the present invention may be linear, branched or cyclic, wherein one or more non-adjacent CH 2 The groups may be replaced by the above groups; in addition, one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 It is preferably replaced by F, Cl or CN, further preferably by F or CN, and particularly preferably by CN.

[0036] Aromatic or heteroaromatic ring systems having 5 to 60 or 5 to 40 aromatic ring atoms which in each case may also be substituted by the abovementioned radicals and which can be attached to the aromatic or heteroaromatic system via any desired position are understood as meaning in particular radicals derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, lettuce, perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, biphenylylidene, terphenyl, biphenylylidene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-indenocarbazole, cis- or trans-indolocarbazole, trimerized indene, isotrimerized indene, spirotrimerized indene, spiroisotrimerized indene, 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, phenanthroline azine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthimidazole, pyridimidazole, pyrazimidazole, quinoxalineimidazole, Azoles, benzo Azoles, naphtho Azoles, anthracenes Azoles, phenanthracenes Azoles, Isopropylamine oxadiazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, hexaazaterphenylene, 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, phen Oxazine, phenothiazine, fluorescent red ring, 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, 1,2,3-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 radicals derived from combinations of these systems.

[0037] In the context of this specification, the expression that two or more groups together can form a ring is understood to mean in particular that the two groups are connected to each other by a chemical bond under the conditions of formal elimination of two hydrogen atoms. This is illustrated by the following scheme:

[0038]

[0039] However, in addition, the above wording should also be understood to mean that if one of the two groups is hydrogen, the second group is bound to the position where the hydrogen atom is bonded, thereby forming a ring. This will be illustrated by the following scheme:

[0040]

[0041] In a preferred configuration, the compound of the present invention may preferably contain at least one structure of formula (I-1) to (I-6), more preferably a compound selected from formula (I-1) to (I-6),

[0042]

[0043] The symbols Ar, Ar a ,Ar b ,Ar c ,Ar d , R a , R b and R c has the definitions given above, especially for formula (I).

[0044] In addition, it is feasible that Ar, Ar a ,Ar b ,Ar c and / or Ar d The radicals are in each case identical or different and are selected from phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, anthracene, pyrene, perylene, letrozole, phenanthrene or terphenylidene, each of which may be substituted by one or more R radicals, preferably phenyl, biphenyl, fluorene, dibenzofuran, terphenylidene, carbazole, indolocarbazole.

[0045] Preferably, Ar a ,Ar b ,Ar c and / or Ar d The radicals are identical or different in each case and are selected from the group consisting of the formula (Ar a -1) to (Ar a -29) structure,

[0046]

[0047]

[0048]

[0049] The symbols used are as follows:

[0050] Y is O, S or NR, preferably O or NR;

[0051] k is independently 0 or 1 in each case;

[0052] i is independently 0, 1 or 2 in each occurrence;

[0053] j is independently 0, 1, 2 or 3 in each case;

[0054] h is independently at each occurrence 0, 1, 2, 3 or 4;

[0055] g is independently at each occurrence 0, 1, 2, 3, 4 or 5;

[0056] R has the meaning given above, in particular for formula (I), and the dashed bond marks the point of attachment.

[0057] Preferably, Ar a and / or Ar b The group is of formula -Ar e -Q structure, where Ar e are identical or different in each case and are aromatic or heteroaromatic ring systems having 5 to 40 aromatic ring atoms and which may be substituted by one or more R groups, preferably Ar e are in each case identical or different and are aryl or heteroaryl radicals having 5 to 30 aromatic ring atoms and which may be substituted by one or more R radicals, preferably selected from phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, anthracene, pyrene, perylene, letrozole, phenanthrene or terphenylidene, each of which may be substituted by one or more R radicals, preferably phenyl, biphenyl, fluorene, dibenzofuran, terphenylidene, carbazole, indolocarbazole; and Q is an electron transporting group, preferably a pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, quinoline, isoquinoline, imidazole and / or benzimidazole radical, which may be substituted by one or more R radicals.

[0058] Preferred aromatic or heteroaromatic ring systems Ar and / or Ar eselected from the group consisting of a benzene subunit; a biphenyl subunit, in particular an o-, m- or p-biphenyl subunit; a terphenyl subunit, in particular an o-, m-, p- or branched terphenyl subunit; a quaterphenyl subunit, in particular an o-, m-, p- or branched quaterphenyl subunit; a fluorene subunit which may be attached via the 1-, 2-, 3- or 4-position; a spirobifluorene subunit which may be attached via the 1-, 2-, 3- or 4-position; a naphthalene subunit, in particular a naphthalene subunit attached via the 1- or 2-position; an indole subunit; a benzofuran subunit subunit; benzothiophene subunit; carbazole subunit which may be linked via the 1, 2, 3, 4 or 9 position; dibenzofuran subunit which may be linked via the 1, 2, 3 or 4 position; benzothiophene subunit which may be linked via the 1, 2, 3 or 4 position; carbazole subunit; indenocarbazole subunit; indolecarbazole subunit; pyridine subunit; pyrimidine subunit; pyrazine subunit; pyridazine subunit; triazine subunit; quinoline subunit; isoquinoline subunit; quinazoline subunit; quinoxaline subunit; phenanthrene subunit or terphenylidene subunit, each of which may be substituted with one or more R groups.

[0059] In another preferred configuration, it is possible that Ar and / or Ar e The radicals are identical or different in each case and are selected from the group consisting of the formula (Ar e -1) to (Ar e -9) structure,

[0060]

[0061]

[0062] The symbols used are as follows:

[0063] j is independently 0, 1, 2 or 3 in each case;

[0064] h is independently at each occurrence 0, 1, 2, 3 or 4;

[0065] R has the meaning given above, in particular for formula (I), and the dashed bond marks the point of attachment.

[0066] In a preferred embodiment, it is possible that the Q groups are identical or different in each case and are selected from the structures of the formulae (Q-1) to (Q-8),

[0067]

[0068] in which R has the meaning given above, in particular for formula (I), and the dashed bond marks the point of attachment.

[0069] In a particularly preferred configuration, it is possible that the Q groups are identical or different in each case and are selected from the structures of the formula (Q-1a), (Q-1b), (Q-1c), (Q-1d), (Q-1e), (Q-1f), (Q-1g), (Q-1h), (Q-1i) and / or (Q-1j),

[0070]

[0071]

[0072] Where R 1 With the definitions given above, in particular for formula (I), the dashed bonds mark the attachment positions, the l references are in each case identical or different and are 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2 or 3, more preferably 0 or 1; the h references are in each case identical or different and are 0, 1, 2, 3 or 4, preferably 0, 1 or 2, more preferably 0 or 1; the j references are in each case identical or different and are 0, 1, 2 or 3, preferably 0, 1 or 2, more preferably 0 or 1. Preference is given to structures of formula (Q-1a).

[0073] In one embodiment, it is possible that the compound comprises at least one structure of formula (I-2), wherein Ar a The group is selected from the formula (Ar a -1) to (Ar a -18) structure, wherein in the formula (Ar a -8) to (Ar a -12), the Y group is preferably O or NR, and Ar d The radicals are identical or different in each case and are selected from the group consisting of the formula (Ar a -1) to (Ar a -23) structure, wherein in the formula (Ar a -8) to (Ar a -12), the Y group is preferably O or NR, wherein Ar d The radicals are identical or different in each case and are preferably selected from the formula (Ar a -1)、(Ar a -2) and (Ar a -7) to (Ar a -18) structure. In this case, in a preferred configuration, Ar d The groups are preferably linked via single bonds, wherein these Ar d The group more preferably forms a carbazole group.

[0074] In one embodiment, it is possible that the compound comprises at least one structure of formula (I-4), wherein the Ar group is selected from the group consisting of e -1) to (Ar e -4) structure, Ar a The group is selected from the formula (Ar a -1) to (Ar a -18) structure, wherein in the formula (Ar a -8) to (Ar a -12), the Y group is preferably O or NR, and Ar d The radicals are identical or different in each case and are selected from the group consisting of the formula (Ar a -1) to (Ar a -23) structure, wherein in the formula (Ar a -8) to (Ar a -12), the Y group is preferably O or NR, wherein Ar d The radicals are identical or different in each case and are preferably selected from the formula (Ar a -1)、(Ar a -2), (Ar a -7) to (Ar a -18) structure. In this case, in a preferred configuration, Ar d Group or Ar d At least one of the groups is connected to the Ar group through a single bond, wherein these Ar d Group or Ar d At least one of the groups together with the Ar group more preferably forms a carbazole group.

[0075] In one embodiment, it is possible that the compound comprises at least one structure of formula (I-3), wherein Ar c The radicals are identical or different in each case and are selected from the group consisting of the formula (Ar a -1) to (Ar a -23) structure, wherein in the formula (Ar a -8) to (Ar a -12), the Y group is preferably O or NR; preferably, Ar c The radicals are identical or different in each case and are selected from the group consisting of the formula (Ar a -1)、(Ar a -2), (Ar a -7) to (Ar a -18) structure; and Ar d The radicals are identical or different in each case and are selected from the group consisting of the formula (Ar a -1) to (Ara -23) structure, wherein in the formula (Ar a -8) to (Ar a -12), the Y group is preferably O or NR, wherein Ar d The radicals are identical or different in each case and are preferably selected from the formula (Ar a -1)、(Ar a -2), (Ar a -7) to (Ar a -18) structure. In this case, in a preferred configuration, Ar c The groups are preferably linked via single bonds, wherein these Ar c The group more preferably forms a carbazole group. In a particularly preferred configuration, Ar c The group in each case and Ar d The groups are linked in each case via a single bond, where these Ar c and Ar d The groups more preferably each form a carbazole group.

[0076] In one embodiment, it is possible that the compound comprises at least one structure of formula (I-5) and / or formula (I-6), wherein the Ar groups are identical or different in each case and are selected from the group consisting of: e -1) to (Ar e -4) structure, Ar c The radicals are identical or different in each case and are selected from the group consisting of the formula (Ar a -1) to (Ar a -23) structure, wherein in the formula (Ar a -8) to (Ar a -12), the Y group is preferably O or NR; preferably, Ar c The radicals are identical or different in each case and are selected from the group consisting of the formula (Ar a -1)、(Ar a -2), (Ar a -7) to (Ar a -18) structure; and Ar d The radicals are identical or different in each case and are selected from the group consisting of the formula (Ar a -1) to (Ar a -18) structure, wherein in the formula (Ar a -8) to (Ar a -12), the Y group is preferably O or NR, wherein Ar d The radicals are identical or different in each case and are preferably selected from the formula (Ar a -1)、(Ar a-2), (Ar a -7) to (Ar a -18) structure. In this case, in a preferred configuration, Ar c Group or Ar c At least one of the groups is preferably linked to the Ar group via a single bond, wherein these Ar c Group or Ar c In another preferred configuration, at least one of the groups together with the Ar group preferably forms a carbazole group. d Group or Ar d At least one of the groups is preferably linked to the Ar group via a single bond, wherein these Ar d Group or Ar d At least one of the groups together with the Ar group more preferably forms a carbazole group. In a particularly preferred configuration, Ar c Group or Ar c At least one of the groups is linked together with the Ar group via a single bond, wherein these groups preferably form a carbazole group, and Ar d Group or Ar d At least one of the groups is linked to the Ar group via a single bond, wherein these groups preferably form a carbazole group. Thus, these particularly preferred compounds have two carbazole groups, one of which contains Ar c group and a carbazole group contains Ar d Group.

[0077] Preferably, the compound comprises at least one structure of formula (I-2), wherein Ar a The group is of formula Ar e -Q structure, where the symbol Ar e and Q have the definitions given above, and Ar d The radicals are identical or different in each case and are selected from the group consisting of the formula (Ar a -1) to (Ar a -23) structure, wherein in the formula (Ar a -8) to (Ar a -12), the Y group is preferably O or NR, wherein Ar d The radicals are identical or different in each case and are preferably selected from the formula (Ar a -1)、(Ar a -2), (Ar a -7) to (Ar a -18) structure. In this case, in a preferred configuration, Ar d The groups are preferably linked via single bonds, wherein these Ar dThe group more preferably forms a carbazole group.

[0078] In addition, it is possible that the compound comprises at least one structure of formula (I-4), wherein the Ar group is selected from the group consisting of e -1) to (Ar e -4) structure, Ar a The group is of formula Ar e -Q structure, where the symbol Ar e and Q have the definitions given above, and Ar d The radicals are identical or different in each case and are selected from the group consisting of the formula (Ar a -1) to (Ar a -23) structure, wherein in the formula (Ar a -8) to (Ar a -12), the Y group is preferably O, wherein Ar d The radicals are identical or different in each case and are preferably selected from the formula (Ar a -1)、(Ar a -2), (Ar a -7) to (Ar a -18) structure. In this case, in a preferred configuration, Ar d Group or Ar d At least one of the groups is connected to the Ar group through a single bond, wherein these Ar d Group or Ar d At least one of the groups together with the Ar group more preferably forms a carbazole group.

[0079] In another configuration, it is possible that the compound comprises at least one structure of formula (I-1) and / or formula (I-2), wherein Ar a The group contains an electron transport group or is an electron transport group, wherein Ar a The radical preferably comprises a pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, quinoline, isoquinoline, imidazole and / or benzimidazole radical or is one of the radicals mentioned, wherein these radicals may be substituted by one or more R radicals, with particular preference being given to triazine radicals.

[0080] Preferably, the compound comprises at least one structure of formula (I-1), wherein Ar b The group contains an electron transport group or is an electron transport group, wherein Ar bThe radical preferably comprises a pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, quinoline, isoquinoline, imidazole and / or benzimidazole radical or is one of the radicals mentioned, wherein these radicals may be substituted by one or more R radicals, with particular preference being given to triazine radicals.

[0081] More preferably, the compound comprises at least one structure of formula (I-1), wherein Ar a The group is of formula Ar e -Q structure and Ar b The group is of formula Ar e -Q structure, where the symbol Ar e and Q have the definitions given above.

[0082] In another configuration, it is possible that the compound comprises at least one structure of formula (I-1), wherein Ar a The group contains an electron transport group or is an electron transport group, wherein Ar a The group preferably contains a pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, quinoline, isoquinoline, imidazole and / or benzimidazole group or is one of the groups mentioned, wherein these groups may be substituted by one or more R groups, wherein triazine groups are particularly preferred, and Ar b The group is selected from the formula (Ar a -1) to (Ar a -18) structure, wherein in the formula (Ar a -8) to (Ar a -12), the Y group is preferably O or NR; wherein Ar a The group is preferably of the formula Ar e -Q structure, where the symbol Ar e and Q have the definitions given above.

[0083] The compounds of the present invention are particularly suitable as host materials for luminophores in electronic devices, preferably as host materials for singlet, triplet and TADF luminophores; electron transport materials; electron injection materials; hole conduction materials; hole injection materials; electron blocking materials; hole blocking materials. The specific properties of the compounds depend on the type and number of the corresponding functional groups. Compounds containing one, two or more electron transport groups but not containing hole transport groups are particularly suitable as host materials, electron transport materials, electron injection materials and / or hole blocking materials. Compounds containing one, two or more hole transport groups but not containing electron transport groups are particularly suitable as host materials, hole conduction materials, hole injection materials and / or electron blocking materials. Compounds containing one, two or more hole transport groups and one, two or more electron transport groups are particularly suitable as host materials.

[0084] Electron transport groups are well known in the art and promote the ability of a compound to transport and / or conduct electrons. Examples of electron transport groups are pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, quinoline, isoquinoline, imidazole and / or benzimidazole groups.

[0085] Hole transport groups are likewise known in the art and they preferably include triarylamine or carbazole groups.

[0086] It is also possible that Ar, Ar b ,Ar c ,Ar d The radical does not contain any triazine group, preferably does not contain any pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, quinoline, isoquinoline, imidazole and / or benzimidazole group, more preferably does not contain any electron transport group.

[0087] Another feasible situation is that Ar, Ar a ,Ar b ,Ar c ,Ar d The radical does not contain any triazine group, preferably does not contain any pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, quinoline, isoquinoline, imidazole and / or benzimidazole group, more preferably does not contain any electron transport group.

[0088] In addition, it is possible that Ar, Ar a ,Ar c ,Ar d The group does not contain any carbazole group, preferably does not contain any carbazole group and / or any group of the formula N(Ar') 2 、N(R 1 ) 2More preferably, it does not contain any hole transporting group.

[0089] Another feasible situation is that Ar, Ar b ,Ar c ,Ar d The group does not contain any carbazole group, preferably does not contain any carbazole group and / or any group of the formula N(Ar') 2 、N(R 1 ) 2 More preferably, it does not contain any hole transporting group.

[0090] It is also possible that Ar, Ar a ,Ar b ,Ar c ,Ar d The group does not contain any carbazole group, preferably does not contain any carbazole group and / or any group of the formula N(Ar') 2 、N(R 1 ) 2 More preferably, it does not contain any hole transporting group.

[0091] Another possible situation is that Ar e The group does not contain any carbazole group, preferably does not contain any carbazole group and / or any group of the formula N(Ar') 2 、N(R 1 ) 2 More preferably, it does not contain any hole transporting group.

[0092] It is further possible that the Q group does not contain any carbazole groups, preferably does not contain any carbazole groups and / or any group of the formula N(Ar′) 2 、N(R 1 ) 2 More preferably, it does not contain any hole transporting group.

[0093] In another preferred embodiment, it is feasible that the compound of the present invention comprises a structure of formula (II-1) to (II-154), wherein the compound of the present invention may be more preferably selected from the compounds of formula (II-1) to (II-154),

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121] The symbols R and R a , R b and R c has the definitions given above, especially for formula (I), and the other symbols are as follows:

[0122] X is the same or different in each instance and is N, CR, or if a group is attached to the structure, X is C; and

[0123] Y is O, S, NR or C(R) 2 , preferably O, NR or C(R) 2 .

[0124] Preferably, in the structures / compounds of formula (II-1) to (II-154), no more than two X groups in each ring are N, preferably all X are CR; preferably at least one X group in each ring, more preferably at least two X groups are selected from CH and CD.

[0125] It is also possible that, in the structures / compounds of formulae (II-1) to (II-154), at least two non-adjacent X groups in each ring are N; the Y group is NR and at least one X group in the ring fused to the ring having the Y group is N and / or the Y group in one ring is NR and one X group in the ring not adjacent to the Y group is N. These structures / compounds preferably contain an electron transport group and are therefore particularly suitable as electron transport materials and / or host materials.

[0126] In another embodiment, it is feasible that in the structures / compounds of formula (II-1) to (II-154), no more than four, preferably no more than two X groups are N; more preferably all X groups are CR, wherein preferably no more than 4, more preferably no more than 3, and especially preferably no more than 2 CR groups represented by X are not CH groups. These structures / compounds preferably do not contain any electron transport groups and are therefore particularly suitable as hole transport materials and / or matrix materials.

[0127] In another preferred embodiment, it is feasible that the compound of the present invention comprises a structure of formula (III-1) to (III-60), wherein the compound of the present invention may be more preferably selected from the compounds of formula (III-1) to (III-60),

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138] The symbols R and R a , R b and R c has the definitions given above, especially for formula (I), and the other symbols are as follows:

[0139] Y is O, S, NR or C(R) 2 , preferably O, NR or C(R) 2 ;

[0140] i is independently 0, 1 or 2 in each occurrence;

[0141] j is independently 0, 1, 2 or 3 in each case;

[0142] h is independently at each occurrence 0, 1, 2, 3 or 4;

[0143] g is independently 0, 1, 2, 3, 4 or 5 at each occurrence.

[0144] The sum of the indices i, j, h and g in the structures / compounds of the formulae (III-1) to (III-60) is preferably not more than 6, particularly preferably not more than 4, more preferably not more than 2.

[0145] In a preferred embodiment of the present invention, it is possible that at least two preferably adjacent R groups together with other groups to which the two R groups are bound form a condensed ring, wherein the two R groups form at least one structure of formula (RA-1) to (RA-13),

[0146]

[0147]

[0148] Where R 1 With the above definitions, the dashed bond represents the point of attachment of the atoms of the group to which the two R groups are bound, and the other symbols have the following definitions:

[0149] Y 1 are identical or different in each case and are C(R 1 ) 2 , (R 1 ) 2 CC(R 1 )2 , (R 1 )C=C(R 1 ), NR 1 , NAr', O or S, preferably C(R 1 ) 2 , (R 1 ) 2 CC(R 1 ) 2 , (R 1 )C=C(R 1 ), O or S;

[0150] R d are identical or different in each case and are F, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, wherein the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may be replaced by one or more R in each case 2 group substitution, where one or more non-adjacent CH 2 The group can be R 2 C=CR 2 、C≡C、Si(R 2 ) 2 ,C=O,C=S,C=Se,C=NR 2 、-C(=O)O-、-C(=O)NR 2 -、NR 2 ,P(=O)(R 2 ), -O-, -S-, SO or SO 2 or having 5 to 60 aromatic ring atoms and in each case being replaced by one or more R 2 Aromatic or heteroaromatic ring systems substituted with a radical or having 5 to 60 aromatic ring atoms and which may be substituted with one or more R 2 substituted aryloxy or heteroaryloxy groups; at the same time, the two R d Group together or one R d Group and R 1 The groups together or with other groups may also form a ring system, wherein R 2 has the definitions given above, in particular for formula (I);

[0151] r is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, more preferably 0 or 1;

[0152] s is 0, 1, 2, 3, 4, 5 or 6, preferably 0, 1, 2, 3 or 4, more preferably 0, 1 or 2;

[0153] t is 0, 1, 2, 3, 4, 5, 6, 7 or 8, preferably 0, 1, 2, 3 or 4, more preferably 0, 1 or 2;

[0154] v is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, preferably 0, 1, 2, 3 or 4, more preferably 0, 1 or 2.

[0155] Preference is given here to structures of the formulae RA-1, RA-3, RA-4 and RA-5, particular preference to structures of the formulae RA-4 and RA-5.

[0156] In a preferred embodiment of the present invention, at least two preferably adjacent R groups together with other groups to which the two R groups are bound form a condensed ring, wherein the two R groups form a structure of formula (RA-1a) to (RA-4f),

[0157]

[0158]

[0159] The dotted bond represents the connection site of the atoms of the group to which the two R groups are bound, the symbol m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and the symbol R 1 , R 2 , R d and the indices s and t have the definitions given above, in particular for formula (I) and / or formulae (RA-1) to (RA-13).

[0160] The structure of formula RA-4f is preferred herein.

[0161] It is also possible that at least two R groups that form the structures of formulae (RA-1) to (RA-12) and / or (RA-1a) to (RA-4f) and form a condensed ring are R groups from adjacent X groups, or are R groups that are each bound to adjacent carbon atoms, wherein these carbon atoms are preferably connected via a bond.

[0162] In another preferred configuration, at least two preferably adjacent R groups preferably form a condensed ring together with other groups to which the two R groups are bound, wherein the two R groups form a structure of formula (RB),

[0163]

[0164] Where R 1 has the definitions given above, in particular for formula (I), the dotted bond represents the bonding site to which the two R groups are attached, the marker m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, Y 2 C(R1 ) 2 NR 1 、NAr'、BR 1 , BAr', O or S, preferably C(R 1 ) 2 , NAr' or O, more preferably C(R 1 ) 2 or O, wherein Ar' has the meaning given above, in particular the meaning given for formula (I).

[0165] It is also possible that at least two R groups forming the structure of formula (RB) and forming a condensed ring are R groups from adjacent X groups, or are R groups each bound to adjacent carbon atoms, wherein these carbon atoms are preferably connected via a bond.

[0166] More particularly, it is possible that in preferred structures / compounds the sum of the indices r, s, t, v, m and n is preferably 0, 1, 2 or 3, more preferably 1 or 2.

[0167] More preferably, the compound comprises at least one structure of formula (IV-1) to (IV-12); more preferably, the compound is selected from the compounds of formula (IV-1) to (IV-12), wherein the compound has at least one fused ring,

[0168]

[0169]

[0170]

[0171] The symbols R and R a , R b and R c Having the definitions given above, in particular for formula (I), the symbol o represents the fusion site of at least one fused ring, and the other indices used are as follows:

[0172] j is independently 0, 1, 2 or 3 in each case;

[0173] h is independently at each occurrence 0, 1, 2, 3 or 4;

[0174] g is independently 0, 1, 2, 3, 4 or 5 at each occurrence.

[0175] It is also possible, especially for structures / compounds of formulae (IV-1) to (IV-12), that the condensed ring is formed by structures of formulae (RA-1) to (RA-13), (RA-1a) to (RA-4f) and / or (RB). As shown above, the condensed ring is preferably formed by structures of formulae (RA-1) to (RA-13) and / or (RA-1a) to (RA-4f).

[0176] Preferably, the compound has at least two fused rings, wherein at least one fused ring is formed by the structure of formula (RA-1) to (RA-13) and / or (RA-1a) to (RA-4f), and the other ring is formed by the structure of formula (RA-1) to (RA-13), (RA-1a) to (RA-4f) or (RB).

[0177] Another possible situation is that the substituents R, R d and R 1 Not with substituents R, R d and R 1 The ring atoms of the ring systems to which they are attached form a fused aromatic or heteroaromatic ring system. This includes the ring atoms that can be attached to substituents R, R d and R 1 Bonded possible substituents R d , R 1 and R 2 A fused aromatic or heteroaromatic ring system is formed.

[0178] R a , R b , R c The radicals preferably do not form any ring systems with other radicals.

[0179] When the compounds of the present invention are aromatic or heteroaromatic R, R d , R 1 or R 2 When the substituents are substituted with aryl or heteroaryl groups, it is preferred that these do not have any aryl or heteroaryl groups with more than two aromatic six-membered rings fused directly to each other. More preferably, the substituents do not have any aryl or heteroaryl groups with six-membered rings fused directly to each other. The reason for this preference is the low triplet energy of such structures. Fused aryl groups with more than two aromatic six-membered rings fused directly to each other but still suitable according to the invention are phenanthrene and terphenylene, since these also have a high triplet energy level.

[0180] It is also possible that the R groups do not contain any aromatic or heteroaromatic ring systems having three linearly condensed aromatic 6-membered rings, wherein preferably none of the R groups contain any aromatic or heteroaromatic ring systems having three linearly condensed aromatic 6-membered rings.

[0181] Preferably, Z a , Z b The group may be the same as Z in formula (I) or in a preferred embodiment of the formula a , Z b The groups to which the groups are bonded form complete conjugation. Once a direct bond is formed between adjacent aromatic or heteroaromatic rings, complete conjugation of the aromatic or heteroaromatic ring system is formed. Other bonds between the above-mentioned conjugated groups, for example bonds via sulfur, nitrogen or oxygen atoms or carbonyl groups, are not detrimental to the conjugation.

[0182] Another possible situation is that according to the above formula, the substituents R and R 1 does not form a fused aromatic or heteroaromatic ring system with the ring atoms of the ring system, preferably does not form any fused ring system. This includes the formation of 1 Possible substituents R for group bonding 1 and R 2 A fused ring system is formed.

[0183] When it can be selected especially from R, R 1 and / or R 2 When two groups of R form a ring system with each other, the ring system may be a monocyclic or polycyclic aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system. In this case, the groups that together form the ring system may be adjacent, which means that these groups are bonded to the same carbon atom or to carbon atoms that are directly bonded to each other, or they may be further away from each other. 1 and / or R 2 The ring systems of can also be connected to one another via bonds, so that this can achieve ring closure. In this case, the respective corresponding bonding sites preferably already have substituents R, R 1 and / or R 2 .

[0184] It is also possible that at least one R group is identical or different in each case and is selected from a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, or is selected from an aromatic or heteroaromatic ring system of the following formulae Ar-1 to Ar-75; preferably, the substituents R form a condensed ring, preferably a condensed ring according to the structure of formula (RA-1) to (RA-13) or (RB), or the substituents R are identical or different in each case and are selected from: an aromatic or heteroaromatic ring system selected from the following formulae Ar-1 to Ar-75, and / or the Ar' groups are identical or different in each case and are selected from the following formulae Ar-1 to Ar-75, and / or Ar a ,Ar b ,Ar c ,Ar d and / or the Ar' groups are in each case identical or different and are selected from the following formulae Ar-1 to Ar-75,

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192] Where R 1 Having the definitions given above, dashed bonds represent bonds to the corresponding radicals, and in addition:

[0193] Ar 1 are identical or different in each case and are aromatic rings having 6 to 18 atoms and may be replaced by one or more R 1 a divalent aromatic or heteroaromatic ring system substituted with a radical;

[0194] A is identical or different in each case and is C(R 1 ) 2 NR 1 , O or S;

[0195] p is 0 or 1, wherein p=0 means Ar 1 The group is not present and the corresponding aromatic or heteroaromatic group is directly bonded to the corresponding group;

[0196] q is 0 or 1, where q=0 means that no A group is bonded to this position, and R 1 The groups are bonded to the corresponding carbon atoms.

[0197] The structures of formulae (Ar-1) to (Ar-75) described in detail above are Ar as defined in the structure of formula (I) a ,Ar b ,Ar c ,Ar d The preferred configuration of the group, in this case, the substituent R in formula (Ar-1) to (Ar-75) 1 is replaced by R, wherein R has the above-mentioned meanings, in particular the meanings given for formula (I).

[0198] The structures of formulae (Ar-1) to (Ar-75) described in detail above are Ar and Ar as defined in the structure of formula (I). eThe preferred configuration of the group, in this case, the substituent R in formula (Ar-1) to (Ar-75) 1 shall be replaced by R, wherein R has the above definitions, in particular the definitions given for formula (I). In addition, Ar and Ar e The group contains additional attachment sites.

[0199] Here, preferred formulas are (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16), (Ar-40), (Ar-41), (Ar-42), (Ar-43), (Ar-44), (Ar -45), (Ar-46), (Ar-69), (Ar-70), and (Ar-75) structures, particularly preferably the structures of formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), and (Ar-16).

[0200] When the above groups for the structures of formula (Ar-1) to (Ar-75) have two or more A groups, all possible options include all combinations from the definition of A. In this case, a preferred embodiment is that one of the A groups is NR 1 and the other A group is C(R 1 ) 2 Or both A groups are NR 1 or those cases where both A groups are O.

[0201] When A is NR 1 When the substituent R bonded to the nitrogen atom 1 Preferably, the aromatic ring has 5 to 24 atoms and may also be replaced by one or more R 2 In a particularly preferred embodiment, the R 1 The substituents are identical or different in each case and are an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, in particular 6 to 18 aromatic ring atoms, which does not have any fused aryl radicals and any fused heteroaryl radicals in which two or more aromatic or heteroaromatic 6-membered ring radicals are fused directly to one another and which may in each case also be replaced by one or more R 2 Phenyl, biphenyl, terphenyl and quaterphenyl are preferred. Further preferred are triazines, pyrimidines and quinazolines as listed above for Ar-47 to Ar-50, Ar-57 and Ar-58, wherein these structures may be substituted by one or more R 2 The group is substituted instead of R 1 replace.

[0202] When A is C(R1 ) 2 When the substituent R bonded to the carbon atom 1 are preferably identical or different in each case and are a straight-chain alkyl radical having 1 to 10 carbon atoms or a branched or cyclic alkyl radical having 3 to 10 carbon atoms or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may also be replaced by one or more R 2 Most preferably, R 1 is a methyl group or a phenyl group. In this case, R 1 The radicals together may also form a ring system, which gives rise to a spiro ring system.

[0203] Next, preferred substituents R, R a , R b , R c and R d .

[0204] In a preferred embodiment of the invention, R is identical or different at each occurrence and is selected from the group consisting of H, D, F, CN, NO 2 ,Si(R 1 ) 3 , B(OR 1 ) 2 , a straight-chain alkyl radical having 1 to 20 carbon atoms or a branched or cyclic alkyl radical having 3 to 20 carbon atoms, wherein the alkyl radical may in each case be replaced by one or more R 1 or have 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms and may in each case be substituted with one or more R 1 Aromatic or heteroaromatic ring systems substituted with radicals.

[0205] In another preferred embodiment of the invention, the substituents R are in each case identical or different and are selected from H, D, F, straight-chain alkyl radicals having 1 to 20 carbon atoms or branched or cyclic alkyl radicals having 3 to 20 carbon atoms, where the alkyl radicals may in each case be replaced by one or more R 1 or have 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms and may in each case be substituted with one or more R 1 Aromatic or heteroaromatic ring systems substituted with radicals.

[0206] It is also possible that at least one R group, preferably one substituent R, is identical or different in each case and is selected from H, D, having 6 to 30 aromatic ring atoms and can be replaced by one or more R 1 Aromatic or heteroaromatic ring system substituted with a radical, or N(Ar') 2The group, more preferably, at least one substituent R is identical or different in each case and is selected from a group having 6 to 30 aromatic ring atoms and can be replaced by one or more R 1 In another preferred embodiment of the invention, the substituents R form a ring according to the structure of formula (RA-1) to (RA-12), (RA-1a) to (RA-4f) or (RB), or the substituents R are in each case identical or different and are selected from H, D, having 6 to 30 aromatic ring atoms and can be replaced by one or more R 1 Aromatic or heteroaromatic ring system substituted with a radical, or N(Ar') 2 More preferably, the R groups, preferably the substituents R, are in each case identical or different and are selected from H, or have 6 to 24 aromatic ring atoms, preferably 6 to 18 aromatic ring atoms, more preferably 6 to 13 aromatic ring atoms and can be replaced by one or more R in each case. 1 Aromatic or heteroaromatic ring systems substituted with radicals.

[0207] It is also possible that at least one R group is a radical having 5 to 13 aromatic ring atoms and can be replaced by one or more R 1 Aromatic or heteroaromatic ring systems substituted with radicals.

[0208] Preferably, at least one radical, preferably one substituent R, is selected from phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or terphenylene, each of which may be substituted by one or more R 1 The expression "substituent" here more particularly means that R is not H. Furthermore, if two or more substituents are present from the aromatic or heteroaromatic radicals mentioned, the substituents R may be identical or different.

[0209] The preferred feasible situation is that R a The group is methyl, ethyl, propyl, or two R groups bonded to the same carbon atom a The group forms a cycloalkyl group having 5 or 6, preferably 5, carbon atoms, wherein R a The radicals are preferably methyl, whereby these radicals may be deuterated.

[0210] The preferred feasible situation is that R b The group is methyl, ethyl, propyl, or two R groups bonded to the same carbon atom. b The group forms a cycloalkyl group having 5 or 6, preferably 5, carbon atoms, wherein R bThe radicals are preferably methyl, whereby these radicals may be deuterated.

[0211] The preferred feasible situation is that R c The groups are H, D, methyl, ethyl, propyl, wherein these groups may be deuterated, wherein R c The group is preferably H or D.

[0212] In a preferred embodiment of the present invention, R d are identical or different in each case and are selected from linear alkyl radicals having 1 to 20 carbon atoms or branched or cyclic alkyl radicals having 3 to 20 carbon atoms, wherein the alkyl radicals may be replaced by one or more R 1 or has 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms and may in each case be substituted by one or more R 2 Aromatic or heteroaromatic ring systems substituted with radicals.

[0213] In another preferred embodiment of the present invention, R d are identical or different in each case and are selected from linear alkyl radicals having 1 to 10 carbon atoms or branched or cyclic alkyl radicals having 3 to 10 carbon atoms, wherein the alkyl radicals may be replaced by one or more R 2 substituted with 6 to 30 aromatic ring atoms and may be substituted with one or more R 2 More preferably, R d are identical or different in each case and are selected from straight-chain alkyl radicals having 1 to 5 carbon atoms or branched or cyclic alkyl radicals having 3 to 5 carbon atoms, wherein the alkyl radicals may be replaced by one or more R 2 or has 6 to 24 aromatic ring atoms, preferably 6 to 18 aromatic ring atoms, more preferably 6 to 13 aromatic ring atoms and may in each case be substituted by one or more R 2 Aromatic or heteroaromatic ring systems substituted with radicals.

[0214] In a preferred embodiment of the present invention, R d are identical or different in each case and are selected from straight-chain alkyl groups having 1 to 6 carbon atoms or cyclic alkyl groups having 3 to 6 carbon atoms, wherein the alkyl groups may be replaced by one or more R 2 or have 6 to 24 aromatic ring atoms and may be substituted by one or more R 2 Aromatic or heteroaromatic ring system substituted with a group; at the same time, two R d The groups together may also form a ring system. More preferably, R dare identical or different in each case and are selected from straight-chain alkyl groups having 1, 2, 3 or 4 carbon atoms or branched or cyclic alkyl groups having 3 to 6 carbon atoms, wherein the alkyl groups may be replaced by one or more R 2 substituted, but preferably unsubstituted, or having 6 to 12 aromatic ring atoms, in particular having 6 aromatic ring atoms and in each case being replaceable by one or more preferably nonaromatic R 2 An aromatic ring system substituted with a group, but preferably unsubstituted; at the same time, the two R d The groups together can form a ring system. Most preferably, R d are identical or different in each case and are selected from straight-chain alkyl groups having 1, 2, 3 or 4 carbon atoms or branched alkyl groups having 3 to 6 carbon atoms. Most preferably, R d is a methyl group or a phenyl group, wherein two phenyl groups together can form a ring system, and the methyl group is preferred to the phenyl group.

[0215] Substituents R, R d or Ar a ,Ar b ,Ar c ,Ar d The preferred aromatic or heteroaromatic ring system represented by Ar' is selected from phenyl; biphenyl, especially o-, m- or p-biphenyl; terphenyl, especially o-, m- or p-terphenyl or branched terphenyl; quaterphenyl, especially o-, m- or p-terphenyl or branched quaterphenyl; fluorene, which may be attached via the 1-, 2-, 3- or 4-position; spirobifluorene, which may be attached via the 1-, 2-, 3- or 4-position; naphthalene, especially 1- bonded or 2-bonded naphthalene; indole; benzofuran; benzothiophene; carbazole which may be attached via the 1, 2, 3 or 4 position; dibenzofuran which may be attached via the 1, 2, 3 or 4 position; dibenzothiophene which may be attached via the 1, 2, 3 or 4 position; indenocarbazole; indolocarbazole; pyridine; pyrimidine; pyrazine; pyridazine; triazine; quinoline; isoquinoline; quinazoline; quinoxaline; anthracene; pyrene; perylene; lettuce; phenanthrene or terphenylene, each of which may be substituted by one or more R, R 1 or R 2The structures Ar-1 to Ar-75 listed above are particularly preferred, and the structures of formula (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16), (Ar-69), (Ar-70), (Ar-75) are preferred, and the structures of formula (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16) are particularly preferred. Regarding the structures Ar-1 to Ar-75, it should be noted that these structures are substituted with the substituent R 1 In the ring system Ar a ,Ar b ,Ar c ,Ar d In the case of these substituents R 1 should be replaced by R, and in R d In the case of these substituents R 1 Should be replaced by R 2 .

[0216] Other suitable R groups are of the formula -Ar 4 -N(Ar 2 )(Ar 3 ) group, wherein Ar 2 ,Ar 3 and Ar 4 are identical or different in each case and have 5 to 24 aromatic ring atoms and may be replaced by one or more R 1 Aromatic or heteroaromatic ring system substituted with a radical. 2 ,Ar 3 and Ar 4 The total number of aromatic ring atoms in is not more than 60, preferably not more than 40.

[0217] Here, Ar 4 and Ar 2 It can also be selected from C(R 1 ) 2 NR 1 , O and S groups are bonded to each other, and / or Ar 2 and Ar 3 By selecting C(R 1 ) 2 NR 1 , O and S groups are bonded to each other. Preferably, Ar 4 and Ar 2 Each of the adjacent positions to the nitrogen atom is connected to each other and Ar 2 and Ar 3In another embodiment of the present invention, Ar 2 ,Ar 3 and Ar 4 The groups are not bonded to each other.

[0218] Preferably, Ar 4 is a radical having 6 to 24 aromatic ring atoms, preferably 6 to 12 aromatic ring atoms and which may in each case be replaced by one or more R 1 More preferably, Ar 4 is selected from o-phenylene, m-phenylene or p-phenylene or o-biphenylene, m-biphenylene or p-biphenylene, each of which may be replaced by one or more R 1 Most preferably, Ar 4 is an unsubstituted benzylidene group.

[0219] Preferably, Ar 2 and Ar 3 are identical or different in each case and have 6 to 24 aromatic ring atoms and can be replaced by one or more R 1 Ar is particularly preferred. 2 and Ar 3 The radicals are in each case identical or different and are selected from: benzene; o-, m- or p-biphenyl; o-, m- or p-terphenyl or branched terphenyl; o-, m- or p-terphenyl or branched terphenyl; o-, m- or p-terphenyl or branched terphenyl; 1-, 2-, 3- or 4-fluorenyl; 1-, 2-, 3- or 4-spirobifluorenyl; 1- or 2-naphthyl; indole; benzofuran; benzothiol phenanthene; 1-carbazole, 2-carbazole, 3-carbazole or 4-carbazole; 1-dibenzofuran, 2-dibenzofuran, 3-dibenzofuran or 4-dibenzofuran; 1-dibenzothiophene, 2-dibenzothiophene, 3-dibenzothiophene or 4-dibenzothiophene; indenocarbazole; indolocarbazole; 2-pyridine, 3-pyridine or 4-pyridine; 2-pyrimidine, 4-pyrimidine or 5-pyrimidine; pyrazine; pyridazine; triazine; phenanthrene or terphenylene, each of which may be substituted by one or more R 1 Most preferably, Ar 2 and Ar 3are in each case identical or different and are selected from: benzene; biphenyl, in particular o-, m- or p-biphenyl; terphenyl, in particular o-, m- or p-terphenyl or a branched terphenyl; quaterphenyl, in particular o-, m- or p-quaterphenyl or a branched quaterphenyl; fluorene, in particular 1-, 2-, 3- or 4-fluorene; or spirobifluorene, in particular 1-, 2-, 3- or 4-spirobifluorene.

[0220] In another preferred embodiment of the present invention, R 1 are in each case identical or different and are selected from H, D, F, CN, a straight-chain alkyl radical having 1 to 10 carbon atoms or a branched or cyclic alkyl radical having 3 to 10 carbon atoms, where the alkyl radical may be replaced by one or more R 2 or have 6 to 24 aromatic ring atoms and may be substituted by one or more R 2 In a particularly preferred embodiment of the present invention, R 1 are in each case identical or different and are selected from H, a straight-chain alkyl group having 1 to 6 carbon atoms, in particular having 1, 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group having 3 to 6 carbon atoms, where the alkyl group may be replaced by one or more R 2 substituted, but preferably unsubstituted, or having 6 to 13 aromatic ring atoms and in each case being substituted by one or more R 5 Radically substituted, but preferably unsubstituted, aromatic or heteroaromatic ring systems.

[0221] In another preferred embodiment of the present invention, R 2 are in each case identical or different and are: H, an alkyl radical having 1 to 4 carbon atoms or an aryl radical having 6 to 10 carbon atoms, which may be substituted by an alkyl radical having 1 to 4 carbon atoms, but is preferably unsubstituted.

[0222] At the same time, in the compounds of the invention processed by vacuum evaporation, the alkyl group preferably has no more than five carbon atoms, more preferably no more than 4 carbon atoms, most preferably no more than 1 carbon atom. For compounds processed from solution, suitable compounds are also those substituted with alkyl groups having up to 10 carbon atoms, especially branched alkyl groups, or with oligomeric aryl groups such as o-, m- or p-terphenyl or branched terphenyl or quaterphenyl groups.

[0223] When the compounds of formula (I) or of the preferred embodiments are used as matrix materials for phosphorescent emitters or in a layer directly adjacent to a phosphorescent layer, it is also preferred that the compounds do not contain any fused aryl or heteroaryl groups in which more than two six-membered rings are directly fused to one another. Phenanthrene and terphenylidene are exceptions, which may be preferred despite the presence of fused aromatic six-membered rings due to their high triplet energy.

[0224] It is also possible that the compound contains exactly two or exactly three structures of formula (I), (I-1) to (I-6), (II-1) to (II-154), (III-1) to (III-60) and / or (IV-1) to (IV-12).

[0225] In a preferred configuration, the compound is selected from compounds of formula (D-1),

[0226]

[0227] Where L 1 The radical is a linking group, preferably a bond or an aromatic or heteroaromatic ring system having 5 to 40, preferably 5 to 30, aromatic ring atoms and which may be substituted by one or more R groups, and the other symbols used have the meanings given above, especially for formula (I), in which L 1 The group replaces the hydrogen atom or the substituent to form a bond with the basic structure; preferably, L 1 Group and Z a , Z b Group bonding.

[0228] In another preferred embodiment of the present invention, L 1 is a bond or an aromatic or heteroaromatic ring system having 5 to 14 aromatic or heteroaromatic ring atoms, preferably an aromatic ring system having 6 to 12 carbon atoms, which may be substituted by one or more R groups, but is preferably unsubstituted, wherein R may have the meanings given above, in particular the meanings given for formula (I). More preferably, L 1 is an aromatic ring system having 6 to 10 aromatic ring atoms or a heteroaromatic ring system having 6 to 13 heteroaromatic ring atoms, each of which may be substituted by one or more R 1 substituted with, but preferably unsubstituted with, R 1 may have the definitions given above, in particular the definitions given for formula (I).

[0229] Preferably, the symbol L shown in formula (D1) 1In particular, the aromatic or heteroaromatic radicals are in each case identical or different and are a bond or an aryl or heteroaryl radical having 5 to 24 ring atoms, preferably 6 to 13 ring atoms, more preferably 6 to 10 ring atoms, so that the aromatic or heteroaromatic radical of the aromatic or heteroaromatic ring system is bonded directly, i.e. via an atom of the aromatic or heteroaromatic radical, to the corresponding atom of the other radical.

[0230] Another possible situation is that L shown in formula (D1) 1 The group comprises an aromatic ring system having no more than four, preferably no more than three, more preferably no more than two fused aromatic and / or heteroaromatic 6-membered rings, preferably without any fused aromatic or heteroaromatic ring system. Therefore, relative to the anthracene structure, the naphthyl structure is preferred. In addition, relative to the naphthyl structure, the fluorenyl, spirobifluorenyl, dibenzofuranyl and / or dibenzothienyl structures are preferred.

[0231] Particularly preferred are unfused structures such as phenyl, biphenyl, terphenyl and / or quaterphenyl structures.

[0232] Suitable aromatic or heteroaromatic ring systems L 1 Examples of are selected from: o-phenylene, m-phenylene or p-phenylene; o-biphenylene, m-biphenylene or p-biphenylene; terphenylene, especially branched terphenylene; quaterphenylene, especially branched quaterphenylene; fluorene; spirobifluorene; dibenzofuranene; dibenzothiophene; and carbazole, each of which may be substituted by one or more R 1 The group is substituted, but preferably is unsubstituted.

[0233] In a preferred configuration, the compound of the present invention can be represented by at least one structure of formula (I), (I-1) to (I-6), (II-1) to (II-154), (III-1) to (III-60) and / or (IV-1) to (IV-12). Preferably, the molecular weight of the compound of the present invention preferably comprising the structure of formula (I), (I-1) to (I-6), (II-1) to (II-154), (III-1) to (III-60) and / or (IV-1) to (IV-12) is greater than 5000 g / mol, preferably not more than 4000 g / mol, particularly preferably not more than 3000 g / mol, especially preferably not more than 2000 g / mol, more particularly preferably not more than 1200 g / mol, most preferably not more than 900 g / mol.

[0234] Furthermore, a feature of the preferred compounds of the invention is that they are sublimable. The molar mass of these compounds is generally less than about 1200 g / mol.

[0235] It is also possible that the compound comprising the structure of formula (I), preferably the compound of formula (I) or preferred embodiments of this structure / compound is not in direct contact with the metal atom and is preferably not a ligand of the metal complex.

[0236] The above-mentioned preferred embodiments can be combined with one another as desired within the limits defined in claim 1. In a particularly preferred embodiment of the invention, the above-mentioned preferences occur simultaneously.

[0237] Examples of preferred compounds according to the above detailed embodiments are the compounds detailed in the following table:

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248] The basic structure of the compound of the present invention can be prepared by the path outlined in the following scheme. Each synthesis step herein, for example, the coupling reaction causing the formation of CC bonds and / or the formation of CN bonds is in principle well known to those skilled in the art. These include Buchwald, Suzuki, Yamamoto, STILLE, HECK, NEGISHI, SONOGASHIRA and HIYAMA reactions.

[0249] Further information concerning the synthesis of the compounds of the invention can be found in the Synthetic Examples.

[0250] The following scheme describes the use of 5,6-dibromo-2,3-dihydro-1,1,2,2,3,3-hexamethyl-1H-indene [1541101-19-2] or its partially or fully deuterated variants to prepare compounds of the present invention. This use should be considered exemplary, and other compounds of the present invention can be obtained by similar synthetic routes starting from different basic structures.

[0251] The synthesis of phenyl compounds to which cyclopentyl groups are fused is well known in the art. Many such compounds, in particular 5,6-dibromo-2,3-dihydro-1,1,2,2,3,3-hexamethyl-1H-indene [1541101-19-2] or its partially or fully deuterated variants, are commercially available. These include, for example, 5,6-dibromo-2,3-dihydro-1,1,2,2,3,3-hexamethyl-1H-indene-4,7-d2 [1541101-31-8] and 5,6-dibromo-2,3-dihydro-1,1,2,2,3,3-hexa(methyl-d 3 )-1H-indene[1541101-25-0].

[0252] The compounds of the present invention having an amine group, in particular compounds comprising structures of formula (I-2) to (I-6), can be obtained starting from 5,6-dibromo-2,3-dihydro-1,1,2,2,3,3-hexamethyl-1H-indene [1541101-19-2] or a partially or fully deuterated variant thereof by the following synthetic route:

[0253] Shows:

[0254] 1) With aryl / heteroaryl boronic acid or aryl / heteroaryl boronic ester ((HO) 2 B-Ar) Suzuki coupling followed by introduction of diarylamine group NAr 1 Ar 2 Buchwald-Hartwig or Ullmann coupling:

[0255]

[0256] 2) With aryl / heteroaryl boronic acid or aryl / heteroaryl boronic ester ((HO) 2 B-Ar 1 ) first Suzuki coupling 1, followed by reaction with aryl / heteroaryl boronic acid or aryl / heteroaryl boronic ester ((HO) 2 B-Ar 2 ) A second Suzuki coupling 2, wherein at least one of the two aryl / heteroaryl boronic acids or aryl / heteroaryl boronic esters comprises an amine or carbazole group:

[0257]

[0258] 3) With diarylamine (HNAr 1 Ar 2 ) first Buchwald-Hartwig or Ullmann coupling 1, followed by diarylamine (HNAr 3 Ar 4 ) Second Buchwald-Hartwig or Ullmann coupling 2:

[0259]

[0260] The compounds of the present invention having electron-deficient heterocycles, especially pyrimidine and triazine, for example compounds comprising the structure of formula (I-1), can be obtained starting from 5,6-dibromo-2,3-dihydro-1,1,2,2,3,3-hexamethyl-1H-indene [1541101-19-2] or its partially or fully deuterated variants by the following synthetic route:

[0261] Shows:

[0262] 1) With aryl / heteroaryl boronic acid or aryl / heteroaryl boronic ester ((HO) 2 Suzuki coupling of 2-(2-(4-nitrophenyl)-2-nitropropene (B-Ar) followed by metalation (lithiation or Grignard formation) and reaction with a chlorodiarylpyrimidine or chlorodiaryltriazine:

[0263]

[0264] 2) With aryl / heteroaryl boronic acid or aryl / heteroaryl boronic ester ((HO) 2 B-Ar 1 ) first Suzuki coupling 1, followed by aryl / heteroaryl boronic acid or aryl / heteroaryl boronic ester ((HO) 2 B-Ar 2 ) A second Suzuki coupling 2, wherein at least one of the two aryl / heteroaryl boronic acids or aryl / heteroaryl boronic esters comprises a heteroaryl group according to the present invention:

[0265]

[0266] 3) Double borylation followed by reaction with halogenated aromatic compounds or halogenated heteroaromatic compounds (Hal-Ar 1 ) first Suzuki coupling 1, followed by a halogenated aromatic compound or a halogenated heteroaromatic compound (Hal-Ar 2 ) The second Suzuki coupling 2, wherein two halogenated aromatic compounds or halogenated heteroaromatic compounds (Hal-Ar 1 ) contains a heteroaryl group according to the invention, so preferably the pyrimidine or triazine can be directly linked to 2,3-dihydro-1,1,2,2,3,3-hexamethyl-1H-indene:

[0267]

[0268] The definitions of the symbols used in the above schemes basically correspond to those for formula (I), and for the sake of clarity, the numbers and complete representations of all symbols are omitted.

[0269] The present invention therefore also provides a process for preparing the compounds of the present invention, wherein a phenyl compound fused to a cyclopentyl group is synthesized and at least one aromatic or heteroaromatic group is introduced, preferably by means of a nucleophilic aromatic substitution reaction or coupling reaction.

[0270] By these methods, if necessary, subsequent purification, for example recrystallization or sublimation, can be obtained in high purity, preferably greater than 99% (with the aid of 1 H NMR and / or HPLC determination) of the compounds of the present invention.

[0271] Compounds of the present invention can also be mixed with polymers. Likewise, these compounds can be covalently incorporated into polymers. This can especially be used for compounds substituted by reactive leaving groups such as bromine, iodine, chlorine, boric acid or boric esters or substituted by reactive polymerizable groups such as olefins or oxetanes. It has been found that these can be used as monomers for making corresponding oligomers, dendrimers or polymers. Oligomerization or polymerization preferably works via halogen functional groups or boric acid functional groups or via polymerizable groups. In addition, polymers can be crosslinked by such groups. Compounds of the present invention and polymers can be used in the form of crosslinked or uncrosslinked layers.

[0272] The present invention therefore also provides an oligomer, polymer or dendrimer containing one or more of the structures of formula (I) and the preferred embodiments of this formula or the compounds of the invention as described in detail above, wherein there are one or more bonds of the compounds of the invention or of the structures of formula (I) and the preferred embodiments of this formula to the polymer, oligomer or dendrimer. According to the structure of formula (I) and the preferred embodiments of this formula or the linkage of the compounds, these thus form side chains of the oligomer or polymer or are bonded within the main chain. The polymer, oligomer or dendrimer may be conjugated, partially conjugated or non-conjugated. The oligomer or polymer may be linear, branched or dendritic. For the repeating units of the compounds of the invention in the oligomers, dendrimers and polymers, the same preferences as above apply.

[0273] To prepare oligomers or polymers, the monomers of the invention are homopolymerized or copolymerized with other monomers. Preference is given to copolymers in which the units of formula (I) or the preferred embodiments described above and below are present in an amount of 0.01 mol % to 99.9 mol %, preferably 5 mol % to 90 mol %, more preferably 20 mol % to 80 mol %. Suitable and preferred comonomers for forming the basic backbone of the polymer are selected from the group consisting of: fluorene (for example according to EP 842208 or WO 2000 / 022026), spirobifluorene (for example according to EP 707020, EP 894107 or WO 2006 / 061181), p-phenylene (for example according to WO 92 / 18552), carbazole (for example according to WO 2004 / 070772 or WO 2004 / 113468), thiophene (for example according to EP 1028136), dihydrophenanthrene (for example according to WO 2005 / 014689), cis- and trans-indenofluorene (for example according to WO 2004 / 041901 or WO 2004 / 113412), ketone (for example according to WO 2005 / 040302), phenanthrene (for example according to WO 2004 / 070772 or WO 2004 / 113468), 2005 / 104264 or WO 2007 / 017066) or other multiples of these units. The polymers, oligomers and dendrimers may also contain other units, such as: hole transport units, especially those based on triarylamines; and / or electron transport units.

[0274] In addition, compounds of the invention that are characterized by a high glass transition temperature are of particular interest. In this regard, compounds of the invention that comprise the structure of formula (I) or the preferred embodiments described above and below are particularly preferred, having a glass transition temperature of at least 70° C., more preferably at least 110° C., even more preferably at least 125° C., and particularly preferably at least 150° C., measured according to DIN 51005 (2005-08 edition).

[0275] In order to process the compounds of the invention from the liquid phase, for example by spin coating or by printing, preparations of the compounds of the invention are required. These preparations may be, for example, solutions, dispersions or emulsions. For this purpose, mixtures of two or more solvents may preferably be used. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, THF, methyl-THF, THP, chlorobenzene, dimethoxybenzene, alkanes, phenoxytoluene, especially 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, α-terpineol, benzothiazole, butyl benzoate, isopropylbenzene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indan, NMP, p-cymene , phenethyl ether, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, 2-methylbiphenyl, 3-methylbiphenyl, 1-methylnaphthalene, 1-ethylnaphthalene, ethyl octanoate, diethyl sebacate, octyl octanoate, heptylbenzene, menthyl isovalerate, cyclohexyl hexanoate, or a mixture of these solvents.

[0276] Therefore, the present invention also provides a kind of preparation or composition, the preparation or composition comprises at least one compound of the present invention and at least one other compound.Other compound can be, for example, a solvent, especially one of the above-mentioned solvents or a mixture of these solvents.If other compound comprises solvent, then the mixture is referred to as preparation in this article.Other compound or can be at least one other organic or inorganic compound that is also used in electronic device, such as luminescent compound and / or other matrix material.Preferably feasible situation is that at least one other compound is selected from fluorescent light emitter, phosphorescent light emitter, light emitter showing TADF, host material, electron transport material, electron injection material, hole conduction material, hole injection material, electron blocking material and hole blocking material, preferably host material.

[0277] The present invention also provides the use of the compound of the invention in electronic devices, especially in organic electroluminescent devices. Preferably, the compound of the present invention is used as a host material, an electron transport material, an electron injection material, a hole conduction material, a hole injection material, an electron blocking material, or a hole blocking material in an electronic device.

[0278] The present invention also provides an electronic device comprising at least one compound according to the present invention. An electronic device in the context of the present invention is a device comprising at least one layer comprising at least one organic compound. The component may also comprise other layers formed entirely of inorganic materials or of inorganic materials.

[0279] The electronic device is more preferably selected from: organic electroluminescent devices (OLED, sOLED, PLED, LEC, etc.), preferably organic light emitting diodes (OLED), small molecule-based organic light emitting diodes (sOLED), polymer-based organic light emitting diodes (PLED), light emitting electrochemical cells (LEC), organic laser diodes (O-lasers), organic plasma light emitting devices (DM Koller et al., Nature Photonics 2008, 1-4); organic integrated circuits (O-ICs), organic field effect transistors (O-FET), organic thin film transistors (O-TFT), organic light emitting transistors (O-LET), organic solar cells (O-SC), organic optical detectors, organic photoreceptors, organic field quenching devices (O-FQD) and organic electrical sensors, preferably organic electroluminescent devices (OLED, sOLED, PLED, LEC, etc.), more preferably organic light emitting diodes (OLED), small molecule-based organic light emitting diodes (sOLED), polymer-based organic light emitting diodes (PLED), especially phosphorescent OLED.

[0280] The organic electroluminescent device comprises a cathode, an anode and at least one luminescent layer. In addition to these layers, the organic electroluminescent device may also comprise other layers, such as 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 generation layers in each case. An intermediate layer having, for example, an exciton blocking function may also be introduced between two luminescent layers. However, it should be noted that each of these layers does not necessarily exist. In this case, the organic electroluminescent device may contain one luminescent layer, or it may contain multiple luminescent layers. If there are multiple luminescent layers, it is preferred that these luminescent layers have multiple luminescent peaks between 380nm and 750nm in total, so that the overall result is white luminescence; in other words, a variety of luminescent compounds that can emit fluorescence or phosphorescence are used in the luminescent layer. A system with three luminescent layers is particularly preferred, wherein the three layers show blue, green and orange or red luminescence. The organic electroluminescent device of the present invention may also be a tandem electroluminescent device, especially a white luminescent OLED.

[0281] The compounds of the present invention can be used in different layers according to the exact structure. Preferably, the organic electroluminescent device comprises a compound of formula (I) or the above preferred embodiment in the light-emitting layer as a host material for a phosphorescent emitter or a light-emitting body exhibiting TADF (thermally activated delayed fluorescence), especially a host material for a phosphorescent emitter. In addition, the compounds of the present invention can also be used in an electron transport layer and / or a hole transport layer and / or an exciton blocking layer and / or a hole blocking layer. More preferably, the compounds of the present invention are used as a host material for a phosphorescent emitter in the light-emitting layer, especially a host material for a red phosphorescent, orange phosphorescent, green phosphorescent or yellow phosphorescent emitter, in an electron transport or hole blocking layer as an electron transport or hole blocking material, or in a hole transport or electron blocking layer as a hole transport or electron blocking material.

[0282] When the compounds of the invention are used as matrix materials for phosphorescent compounds in an emitting layer, they are preferably used in combination with one or more phosphorescent materials (triplet emitters). In the context of the present invention, phosphorescence is understood to mean luminescence from excited states with high spin multiplicity, i.e. spin state>1, especially luminescence from excited triplet states. In the context of the present application, all luminescent complexes with transition metals or lanthanides, especially all iridium, platinum and copper complexes, are considered to be phosphorescent compounds.

[0283] Based on the overall mixture of emitter and matrix material, the mixture of the compound according to the invention and the emitting compound contains between 99% by volume and 1% by volume, preferably between 98% by volume and 10% by volume, more preferably between 97% by volume and 60% by volume, and in particular between 95% by volume and 80% by volume of the compound according to the invention. Correspondingly, based on the overall mixture of emitter and matrix material, the mixture contains between 1% by volume and 99% by volume, preferably between 2% by volume and 90% by volume, more preferably between 3% by volume and 40% by volume, and in particular between 5% by volume and 20% by volume of the emitter.

[0284] In one embodiment of the invention, the compounds according to the invention are employed here as sole matrix material (“single host”) for the phosphorescent emitter.

[0285] A further embodiment of the present invention is the use of the compounds according to the invention in combination with other matrix materials as matrix material for phosphorescent emitters. Suitable matrix materials which can be used in combination with the compounds according to the invention are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, for example according to WO 2004 / 013080, WO 2004 / 093207, WO 2006 / 005627 or WO 2010 / 006680; triarylamines; carbazole derivatives, for example CBP (N,N-dicarbazolylbiphenyl) or the carbazole derivatives disclosed in WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 288381, EP 1205527, WO 2008 / 086851 or WO 2013 / 041176; indolocarbazole derivatives, for example according to WO 2007 / 063754 or WO 2008 / 056746; indenocarbazole derivatives, for example according to WO 2010 / 136109, WO 2011 / 000455, WO 2013 / 041176 or WO 2013 / 056776; azacarbazole derivatives, for example according to EP 1617710, EP 1617711, EP 1731584, JP2005 / 347160; bipolar matrix materials, for example according to WO 2007 / 137725; silanes, for example according to WO 2005 / 111172; borazolidines or boric acid esters, for example according to WO 2006 / 117052; triazine derivatives, for example according to WO 2007 / 063754, WO 2008 / 056746, WO 2010 / 015306, WO 2011 / 057706, WO 2011 / 060859 or WO2011 / 060877; zinc complexes, for example according to EP 652273 or WO 2009 / 062578; siladiazacyclopentane or siladiazacyclopentane derivatives, for example according to WO 2010 / 054729; phosphodiazacyclopentane derivatives, for example according to WO2010 / 054730; bridged carbazole derivatives, for example according to WO 2011 / 042107, WO 2011 / 060867, WO 2011 / 088877 and WO 2012 / 143080; terphenylidene derivatives, for example according to WO 2012 / 048781; dibenzofuran derivatives, for example according to WO 2015 / 169412, WO 2016 / 015810, WO 2016 / 023608, WO 2017 / 148564 or WO 2017 / 148565; or bicarbazoles, for example according to JP 3139321 B2.

[0286] It is likewise possible that further phosphorescent emitters which emit at a shorter wavelength than the wavelength of the actual emitter are present in the mixture as co-hosts. Particularly good results are obtained when the emitter used is a red phosphorescent emitter and the co-host used in combination with the compounds according to the invention is a yellow phosphorescent emitter.

[0287] In addition, the co-host used can be a compound that participates in charge transport but not to a significant extent, as described in, for example, WO 2010 / 108579. Particularly suitable as a co-host material in combination with the compounds of the present invention are compounds that have a large band gap and that themselves participate in the charge transport of the light-emitting layer at least not to a significant extent. Such materials are preferably pure hydrocarbons. Examples of such materials can be found, for example, in WO 2009 / 124627 or in WO 2010 / 006680. In this case, it should be emphasized that the compounds of the present invention have the advantageous properties of not having specific functional groups such as hole transport groups and / or electron transport groups.

[0288] Suitable phosphorescent compounds (=triplet emitters) are, in particular, compounds which emit light when suitably excited, preferably in the visible region, and which also contain at least one atom, in particular a metal, having an atomic number greater than 20, preferably greater than 38 and less than 84, more preferably greater than 56 and less than 80. Phosphorescent emitters preferably used are compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, in particular compounds containing iridium or platinum.

[0289] Examples of the above-mentioned emitters can be found in the following 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 and WO 2018 / 011186. In general, all phosphorescent complexes for phosphorescent electroluminescent devices according to the prior art and as known to the person skilled in the art in the field of organic electroluminescence are suitable, and the person skilled in the art will be able to use other phosphorescent complexes without inventive step.

[0290] Examples of phosphorescent dopants are listed in the table below:

[0291]

[0292]

[0293]

[0294]

[0295] The compounds according to the invention are also particularly suitable as matrix materials for phosphorescent emitters in organic electroluminescent devices, as described, for example, in WO 98 / 24271, US 2011 / 0248247 and US 2012 / 0223633. In these multicolor display components, an additional blue emitting layer is applied by vapor deposition over the entire area to all pixels, including pixels with non-blue colors.

[0296] In another embodiment of the invention, the organic electroluminescent device according to the invention does not contain any separate hole injection layer and / or hole transport layer and / or hole blocking layer and / or electron transport layer, meaning that the light-emitting layer is directly adjacent to the hole injection layer or the anode, and / or the light-emitting layer is directly adjacent to the electron transport layer or the electron injection layer or the cathode, as described, for example, in WO 2005 / 053051. In addition, metal complexes identical or similar to the metal complexes in the light-emitting layer can be used as hole transport or hole injection materials directly adjacent to the light-emitting layer, as described, for example, in WO 2009 / 030981.

[0297] In other layers of the organic electroluminescent device of the present invention, any material commonly used according to the prior art can be used. Therefore, those skilled in the art will be able to use any known material for organic electroluminescent devices in combination with the compounds of the present invention of formula (I) or the above-mentioned preferred embodiments without paying creative work.

[0298] Furthermore, an organic electroluminescent device is preferred, characterized in that one or more layers are applied by a sublimation process. In this case, the organic electroluminescent device is applied by sublimation in a vacuum sublimation system at a temperature of less than 10 -5 mbar, preferably less than 10 -6 The material is applied by vapor deposition at an initial pressure of 10 mbar. Alternatively, the initial pressure may be even lower, for example less than 10 -7 millibar.

[0299] Likewise preferred is an organic electroluminescent device, characterized in that one or more layers are applied by the OVPD (organic vapor phase deposition) method or by means of carrier gas sublimation. -5 The material is applied at a pressure of between mbar and 1 bar. A special case of this method is the OVJP (Organic Vapor Phase Jet Printing) method, in which the material is applied directly through a nozzle and thereby structured.

[0300] Additionally preferred is an organic electroluminescent device, characterized in that one or more layers are produced from solution, for example by spin coating, or by any printing method such as screen printing, flexographic printing, offset printing, LITI (light-induced thermography, thermal transfer), inkjet printing or nozzle printing. For this purpose, soluble compounds, obtained for example by suitable substitution, are required.

[0301] The formulations using the compounds of formula (I) or the preferred embodiments thereof detailed above are novel. Therefore, the present invention also provides a formulation comprising at least one solvent and a compound according to formula (I) or the preferred embodiments thereof detailed above.

[0302] Furthermore, hybrid methods are possible, for example in which one or more layers are applied from solution and one or more other layers are applied by vapor deposition.

[0303] The person skilled in the art is generally aware of these processes and can apply them without inventive step to organic electroluminescent devices comprising the compounds according to the invention.

[0304] Compound of the present invention and organic electroluminescent device of the present invention are particularly significantly low in refractive index (RI) relative to the prior art. In addition, these compounds and the organic electroluminescent device obtained therefrom show improved lifespan. Meanwhile, other electronic properties of the electroluminescent device such as efficiency or operating voltage at least remain equally good. In another variant, compared with the prior art, compound of the present invention and organic electroluminescent device of the present invention especially have the characteristics of improved efficiency and / or operating voltage and longer lifespan.

[0305] The electronic device of the present invention, especially the organic electroluminescent device, has one or more of the following surprising advantages compared with the prior art:

[0306] 1. An electronic device, especially an organic electroluminescent device, comprising a compound of formula (I) or the preferred embodiments described above and below, especially as a matrix material, as an electron-conducting material or as a hole-conducting material has excellent efficiency. In this case, the compound of the invention having the structure of formula (I) or the preferred embodiments described above and below can produce a low operating voltage when used in an electronic device.

[0307] 2. Electronic devices, in particular organic electroluminescent devices, comprising compounds of formula (I) or of the preferred embodiments described above and below, especially as matrix materials, as electron-conducting materials or as hole-conducting materials have very good lifetimes. In this case, these compounds bring about in particular a low roll-off, i.e. a small drop in the power efficiency of the device at high luminous densities.

[0308] 3. The compounds of the invention of formula (I) or of the preferred embodiments described above and below exhibit very high stability and longevity.

[0309] 4. Electronic devices, especially organic electroluminescent devices, comprising the compounds of the formula (I) or of the preferred embodiments described above and below, especially as matrix material, as electron-conducting material or as hole-conducting material have a very low refractive index.

[0310] 5. By using the compounds of formula (I) or the preferred embodiments described above and below, the formation of optical loss channels in electronic devices, especially organic electroluminescent devices, can be avoided. As a result, these devices are characterized by high PL efficiency of the emitter and thus high EL efficiency, and excellent energy transfer from the matrix to the dopant.

[0311] 6. The compounds of formula (I) or of the preferred embodiments described above and below have excellent glass film formation.

[0312] 7. The compounds of the formula (I) or of the preferred embodiments described above and below form very good films from solution.

[0313] These above-mentioned advantages are not accompanied by very serious degradation of other electronic properties.

[0314] It should be noted that the scope of the present invention encompasses variations of the embodiments described in the present invention. Unless any feature disclosed in the present invention is explicitly excluded, it can be exchanged with an alternative feature having the same purpose or an equivalent or similar purpose. Therefore, unless otherwise specified, any feature disclosed in the present invention should be regarded as an example of a general series or an equivalent or similar feature.

[0315] Unless specific features and / or steps are mutually exclusive, all features of the present invention can be combined with each other in any way. This is especially true for the preferred features of the present invention. Likewise, features of non-essential combinations can be used alone (and not in combination).

[0316] It should also be noted that many features of the present invention, especially those of the preferred embodiments, should be considered creative in themselves, not just as some embodiments of the present invention. For these features, independent protection may be sought as a supplement or alternative to any currently claimed invention.

[0317] The technical teachings disclosed in the present invention may be refined and combined with other embodiments.

[0318] The present invention is illustrated in detail by the following examples, but it is by no means intended to limit the present invention thereby. Those skilled in the art will be able to use the information provided to implement the present invention within the entire scope disclosed without inventive effort, to prepare other compounds of the present invention and to use them in electronic devices, or to employ the methods of the present invention. Example

[0319] Unless otherwise stated, the following synthesis was carried out in anhydrous solvents under a protective gas atmosphere. Metal complexes require additional handling under light protection or yellow light. Solvents and reagents can be purchased from, for example, Sigma-ALDRICH or ABCR. The corresponding numbers in square brackets or the numbers quoted for individual compounds are related to the CAS numbers of the compounds known from the literature. In the case of compounds that can have multiple enantiomers, diastereomers or tautomer forms, one form is shown in a representative manner.

[0320] Synthon LS known from the literature:

[0321]

[0322] A) Synthesis of Synthon S:

[0323] Example S1:

[0324]

[0325] The process is similar to C.-G-Dong et al., Synlett, 2009, No. 7, p. 1081, Table 2, entry 3. Starting materials: 36.0 g (100 mmol) of LS1, 12.0 g (100 mmol) of phenylboronic acid, 3% Pd(PPh 3 ) 4 +9% Ph 3 P, toluene, 80°C, 16 hours. Yield: 28.7 g (80 mmol) 80%; purity: about 97%, according to 1 H NMR.

[0326] The following compounds can be prepared similarly:

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342] B) Synthesis of the compounds of the present invention

[0343] Embodiment A1:

[0344]

[0345] To a solution of 35.7 g (100 mmol) of S1 and 38.6 g (120 mmol) of di-p-benzidine [102113-98-4] in 500 ml of toluene, 4.0 ml (4.0 mmol) of a 1.0 M toluene solution of tri-tert-butylphosphine, 449 mg (2 mmol) of palladium acetate and 15.4 g of sodium tert-butoxide (160 mmol) were added, and the mixture was heated to reflux for 16 hours. The reaction mixture was cooled to room temperature, diluted with toluene and filtered through a diatomaceous earth bed. The filtrate was concentrated under reduced pressure and the residue was crystallized from ethyl acetate / n-heptane. The crude product was crystallized by hot extraction (typical organic solvents, preferably acetonitrile or a mixture of acetonitrile / dichloromethane, 4:1 to 1:4, volume: volume) or chromatography (Torrent automatic column system of A. Semrau) and zone sublimation twice under reduced pressure (p ~ 10 -5 mbar, T~280°C). Yield: 44.8 g (75 mmol) 75%. Purity>99.9% according to HPLC.

[0346] The following compounds can be prepared similarly:

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363] Embodiment A100:

[0364]

[0365] The process is similar to JL Bolliger et al., Chem. Eur. J., 2010, vol. 16, p. 4075, Table 1, entry 28. Starting materials: 36.0 g (100 mmol) of LS1, 40.2 g (110 mmol) of B-[4-([1,1′-biphenyl]-4-ylphenylamino)phenyl]boronic acid [1084334-86-0]. The crude product is purified by chromatography and repeated hot extractive crystallization (conventional organic solvents or combinations thereof, preferably acetonitrile-DCM, 1:3 to 3:1, volume: volume) and fractional sublimation or heat treatment under high vacuum. Yield: 45.6 g (76 mmol), 76%; purity: about 99.9%, according to HPLC.

[0366] The following compounds can be prepared similarly:

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392] Embodiment A300:

[0393]

[0394] The process is similar to that of T. Taisei et al., Chem. Lett., 2019, 48, 1160. Synthesis of 3c. Starting materials: 18.0 g (50 mmol), 26.7 g (110 mmol) of 3-phenyl-9H-carbazole [103012-26-6]. The crude product is purified by chromatography and repeated hot extraction crystallization (conventional organic solvents or combinations thereof, preferably acetonitrile-DCM, 1:3 to 3:1, volume: volume) and fractional sublimation or heat treatment under high vacuum. Yield: 13.7 g (20 mmol), 40%; purity: about 99.9%, according to HPLC.

[0395] If 25 mmol of the first amine / carbazole are initially added and then, after a reaction time of 6 hours, 25 mmol of the second amine / carbazole are added, asymmetrically substituted compounds can be obtained.

[0396] The following compounds can be prepared similarly:

[0397]

[0398]

[0399]

[0400] In addition, the following synthons were synthesized by the method described for the preparation of A300:

[0401]

[0402] Among other compounds, the synthons detailed above were used to prepare compounds A400 to A409 of the invention.

[0403] Embodiment A400:

[0404]

[0405] To a well-stirred solution of 26.1 g (50 mmol) of S100 in 500 ml of THF cooled to 0°C was added dropwise 42.3 ml (55 mmol) of a 1.3 M THF solution of isopropylmagnesium chloride-lithium chloride complex. The mixture was stirred for 1 hour, then 200 ml of a solution of 1 g (60 mmol) in 2-chloro-4,6-diphenyl-1,3,5-triazine [3842-55-5] was added dropwise, the mixture was allowed to warm to room temperature, and stirred at 60°C for 5 hours. The reaction was carefully quenched by adding 50 ml of methanol, the solvent was substantially removed under reduced pressure, the residue was dissolved in 500 ml of dichloromethane (DCM), and the mixture was washed three times with 200 ml of water each time, once with 200 ml of saturated sodium chloride solution, and dried over magnesium sulfate. The desiccant was filtered off, and the filtrate was concentrated to about 200 ml under reduced pressure, by continuously replacing the distilled DCM with methanol. The crystallized product is filtered, washed twice with 50 ml of methanol each time, and dried under reduced pressure. The crude product is purified by chromatography and repeated hot extractive crystallization (conventional organic solvents or combinations thereof, preferably acetonitrile-DCM, 1:3 to 3:1, volume: volume) and fractional sublimation or heat treatment under high vacuum. Yield: 26.5 g (39 mmol), 78%; purity: about 99.9%, according to HPLC.

[0406] The following compounds can be prepared similarly:

[0407]

[0408]

[0409]

[0410] Example: Fabrication of OLEDs

[0411] 1) Vacuum treated devices:

[0412] The OLEDs according to the invention and the OLEDs according to the prior art are produced by the general method according to WO 2004 / 058911, which is adapted to the circumstances described here (layer thicknesses, variation of materials used).

[0413] In the examples that follow, the results for various OLEDs are presented. Clean glass plates (cleaned in a Miele laboratory glass washer, Merck Extran detergent) coated with 50 nm thick structured ITO (indium tin oxide) were pretreated with UV ozone for 25 minutes (UVP PR-100 UV ozone generator). These coated glass plates formed the substrates for the application of the OLEDs.

[0414] 1a) Blue fluorescent OLED component - BF:

[0415] The compounds of the invention can be used in hole injection layers (HIL), hole transport layers (HTL), electron blocking layers (EBL) and electron transport layers (ETL). All materials are applied by thermal vapor deposition in a vacuum chamber. The emitting layer (EML) here always consists of at least one matrix material (host material) SMB (see Table 1) and a luminescent dopant (dopant, luminophore) D, which is added to the (one or more) matrix materials in a specific volume ratio by co-evaporation. Detailed information given in the form of, for example, SMB:D (97:3%) means here that the material SMB is present in the layer in a volume ratio of 97% and the dopant D is present in the layer in a volume ratio of 3%. Similarly, the electron transport layer can also consist of a mixture of two materials; see Table 1. The materials used for the production of OLEDs are shown in Table 5 or are related to the synthesis examples detailed above.

[0416] The OLEDs were characterized in a standard manner. For this purpose, the electroluminescence spectrum was determined, the current efficiency (measured in cd / A), the power efficiency (measured in lm / W) and the external quantum efficiency (EQE, measured in %) were calculated as a function of the luminous density from the current-voltage-luminous density characteristic (IUL characteristic) assuming Lambertian luminescence behavior, and the lifetime was also determined. 2 The EQE in % and the voltage in V are reported at a luminous density of 10000 cd / m 2 The lifetime is determined at an initial luminous density of . The measurement period in which the reference brightness drops to 80% of the initial brightness is set as 100%. The lifetime of the OLED components containing the compounds of the invention is reported as a percentage relative to the reference.

[0417] OLEDs have the following layer structure:

[0418] Base

[0419] Hole injection layer (HIL) consisting of HTM1 doped with 5% NDP-9 (available from Novaled), 20 nm

[0420] Hole transport layer (HTL), see Table 1

[0421] Electron blocking layer (EBL), see Table 1

[0422] Emission layer (EML), see Table 1

[0423] Electron transport layer (ETL), see Table 1

[0424] Electron injection layer (EIL) composed of ETM2, 1nm

[0425] Cathode made of aluminum, 100nm

[0426] Table 1: Structure of blue fluorescent OLED components

[0427]

[0428]

[0429] Table 2: Results of blue fluorescent OLED components

[0430]

[0431] 1b) Phosphorescent OLED components:

[0432] Compound A according to the invention can be used as matrix material (host material) M (see Table 5) or A (see materials according to the invention) in hole injection layers (HIL), hole transport layers (HTL), electron blocking layers (EBL) and emitting layers (EML). For this purpose, all materials are applied by thermal vapor deposition in a vacuum chamber. The emitting layer here always consists of at least one or more than one matrix material M and a phosphorescent dopant Ir, which is added to the (one or more) matrix materials in a specific volume ratio by co-evaporation. Detailed information given in a form such as M1:M2:Ir (55%:35%:10%) means here that the material M1 is present in the layer in a volume ratio of 55%, M2 is present in the layer in a volume ratio of 35%, and Ir is present in the layer in a volume ratio of 10%. Similarly, the electron transport layer can also consist of a mixture of two materials. The exact structure of the OLED can be found in Table 3. The materials used to produce the OLED are shown in Table 5 or are related to the synthesis examples detailed above.

[0433] The OLEDs were characterized in a standard manner. For this purpose, the electroluminescence spectrum was determined, the current efficiency (measured in cd / A), the power efficiency (measured in lm / W) and the external quantum efficiency (EQE, measured in %) were calculated as a function of the luminous density from the current-voltage-luminous density characteristic (IUL characteristic) assuming Lambertian luminescence characteristics, and the lifetime was also determined. 2 EQE in % and voltage in V are reported at luminous density of 1000 cd / m for blue and red. 2 The lifetime is measured at an initial luminous density of 10000 cd / m for green and yellow. 2 The lifetime is determined at an initial luminous density of . The measurement period in which the reference brightness drops to 80% of the initial brightness is set as 100%. The lifetime of the OLED components containing the compounds of the invention is reported as a percentage relative to the reference.

[0434] OLEDs have the following layer structure:

[0435] Base

[0436] Hole injection layer (HIL) consisting of HTM1 doped with 5% NDP-9 (available from Novaled), 20 nm

[0437] Hole transport layer (HTL), see Table 3

[0438] Electron blocking layer (EBL), see Table 3

[0439] Emission layer (EML), see Table 3

[0440] Hole blocking layer (HBL), see Table 3

[0441] Electron transport layer (ETL), composed of ETM1:ETM2 (50%:50%), 30nm

[0442] Electron injection layer (EIL) composed of ETM2, 1nm

[0443] Cathode made of aluminum, 100nm

[0444] Table 3: Structure of phosphorescent OLED components

[0445]

[0446]

[0447]

[0448]

[0449]

[0450] Table 4: Results for phosphorescent OLED components

[0451]

[0452]

[0453] Table 5: Structural formula of materials used

[0454]

[0455]

[0456]

Claims

1. A compound comprising at least one structure of formula (I), preferably a compound of formula (I), The symbols are as follows: Z a are in each case identical or different and are Ar a 、N(Ar c )2 or (Ar)N(Ar c )2; Z b are in each case identical or different and are Ar b 、N(Ar d )2 or (Ar)N(Ar d )2; R a are in each case identical or different and are straight-chain alkyl, alkoxy or thioalkoxy radicals having 1 to 10 carbon atoms or branched or cyclic alkyl, alkoxy or thioalkoxy radicals having 3 to 10 carbon atoms, each of which may be replaced by one or more R 2 The group is preferably a linear alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, each of which may be substituted by one or more R 2 At the same time, two or more preferably adjacent substituents R a Together they can form a ring system; R b are in each case identical or different and are straight-chain alkyl, alkoxy or thioalkoxy radicals having 1 to 10 carbon atoms or branched or cyclic alkyl, alkoxy or thioalkoxy radicals having 3 to 10 carbon atoms, each of which may be replaced by one or more R 2 The group is preferably a linear alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, each of which may be substituted by one or more R 2 Group substitution; at the same time, two adjacent substituents R b Together they can form a ring system; R c are in each case identical or different and are H, D, a linear alkyl, alkoxy or thioalkoxy group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 10 carbon atoms, each of which may be replaced by one or more R 2 A group is substituted, preferably H, D, a linear alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, each of which may be substituted by one or more R 2 The group is substituted, preferably H, D, a straight-chain alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably H, D; Ar a ,Ar b ,Ar c ,Ar d are identical or different in each case and are an aromatic or heteroaromatic ring system having 6 to 60 aromatic ring atoms and which may be substituted by one or more R groups; at the same time, two Ar groups bonded to the same nitrogen atom c ,Ar d The groups may also be bridged to each other via a single bond or a bridging group selected from the following groups: B(R), C(R)2, Si(R)2, C=O, C=NR, C=C(R)2, RC=CR, O, S, S=O, SO2, N(R), P(R), P(=O)R and an ortho-attached phenylene group which may be substituted with one or more R groups, the bridging group preferably being selected from the group consisting of: C(R)2, O, N(R) and an ortho-attached phenylene group which may be substituted with one or more R groups; preferably, Ar a ,Ar b ,Ar c ,Ar d are identical or different in each case and are aryl or heteroaryl radicals having 6 to 40 aromatic ring atoms and which may be substituted by one or more R radicals; at the same time, two Ar, Ar c ,Ar d The groups may also be bridged to each other via a single bond or a bridging group selected from the group consisting of B(R), C(R)2, Si(R)2, C=O, C=NR, C=C(R)2, RC=CR, O, S, S=O, SO2, N(R), P(R), P(=O)R and an ortho-attached phenylene group which may be substituted with one or more R groups, the bridging group preferably being selected from the group consisting of C(R)2, O, N(R) and an ortho-attached phenylene group which may be substituted with one or more R groups; Ar is identical or different in each case and is a linked aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and which may be substituted by one or more R groups; at the same time, one Ar group and one Ar group bonded to the same nitrogen atom c ,Ar d One or both of the groups together may also be bridged to each other via a single bond or a bridging group selected from the group consisting of B(R), C(R)2, Si(R)2, C=O, C=NR, C=C(R)2, RC=CR, O, S, S=O, SO2, N(R), P(R), P(=O)R and an ortho-bound phenylene group which may be substituted by one or more R groups, the bridging group preferably being selected from the group consisting of C(R)2, O, N(R) and an ortho-bound phenylene group which may be substituted by one or more R groups; preferably, Ar is in each case identical or different and is an aryl or heteroaryl group having 5 to 40 aromatic ring atoms and which may be substituted by one or more R groups; at the same time, one Ar group and one Ar bonded to the same nitrogen atom may be substituted by one or more R groups. c ,Ar d One or both of the groups together may also be bridged to each other via a single bond or a bridging group selected from the following groups: B(R), C(R)2, Si(R)2, C=O, C=NR, C=C(R)2, RC=CR, O, S, S=O, SO2, N(R), P(R), P(=O)R and an ortho-attached benzylidene group which may be substituted by one or more R groups, the bridging group preferably being selected from the group consisting of: C(R)2, O, N(R) and an ortho-attached benzylidene group which may be substituted by one or more R groups; R is in each case identical or different and is H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar')2, N(R 1 )2,C(=O)N(Ar')2,C(=O)N(R 1 )2,C(Ar')3,C(R 1 )3,Si(Ar')3,Si(R 1 )3,B(Ar')2,B(R 1 )2,C(=O)Ar′,C(=O)R 1 , P(=O)(Ar')2, P(=O)(R 1 )2,P(Ar')2,P(R 1 )2,S(=O)Ar',S(=O)R 1 ,S(=O)2Ar',S(=O)2R 1 , OSO2Ar', OSO2R 1 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, wherein the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may in each case be replaced by one or more R 1 group, wherein one or more non-adjacent CH2 groups may be replaced by R 1 C=CR 1 、C≡C、Si(R 1 )2. C=O, C=S, C=Se, C=NR 1 、-C(=O)O-、-C(=O)NR 1 -、NR 1 ,P(=O)(R 1 ), -O-, -S-, SO or SO2, or has 5 to 60 aromatic ring atoms and can be replaced by one or more R in each case 1 An aromatic or heteroaromatic ring system substituted with a radical, or having 5 to 60 aromatic ring atoms and substituted by one or more R 1 At the same time, the two R groups can also form a ring system together or with other groups; Ar' is identical or different in each case and is a ring having 5 to 60 aromatic ring atoms and may be replaced by one or more R 1 At the same time, two Ar' groups bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom may also be bridged to each other by a single bond or a bridging group selected from the following groups: B(R 1 )、C(R 1 )2、Si(R 1 )2. C=O, C=NR 1 , C=C(R 1 )2, O, S, S=O, SO2, N(R 1 )、P(R 1 ) and P(=O)R 1 ; R 1 are in each case identical or different and are H, D, F, Cl, Br, I, CN, NO2, N(Ar")2, N(R 2 )2,C(=O)Ar”,C(=O)R 2 ,P(=O)(Ar”)2,P(Ar”)2,B(Ar”)2,B(R 2 )2,C(Ar”)3,C(R 2 )3, Si(Ar”)3, Si(R 2 )3, a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R 2 group, wherein one or more non-adjacent CH2 groups may be replaced by -R 2 C=CR 2 -、-C≡C-、Si(R 2 )2. C=O, C=S, C=Se, C=NR 2 、-C(=O)O-、-C(=O)NR 2 -、NR 2 ,P(=O)(R 2 ), -O-, -S-, SO or SO2 replaced and one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be replaced by one or more R 2 or having 5 to 60 aromatic ring atoms and may be substituted with one or more R 2 substituted aryloxy or heteroaryloxy groups, or having 5 to 60 aromatic ring atoms and may be replaced by one or more R 2 substituted aralkyl or heteroaralkyl groups, or combinations of these systems; at the same time, two or more preferably adjacent R 1 The groups together can form a ring system; at the same time, one or more R 1 The group may form a ring system with the rest of the compound; Ar" is identical or different in each case and is a radical having 5 to 30 aromatic ring atoms and may be replaced by one or more R 2 At the same time, two Ar" groups bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom may also be bridged to each other by a single bond or a bridging group selected from the following groups: B(R 2 )、C(R 2 )2、Si(R 2 )2. C=O, C=NR 2 , C=C(R 2 )2, O, S, S=O, SO2, N(R 2 )、P(R 2 ) and P(=O)R 2 ; R 2 are in each case identical or different and are selected from H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms and in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN, and which may be substituted by one or more alkyl radicals each having 1 to 4 carbon atoms; at the same time, two or more preferably adjacent substituents R 2 Together they can form a ring system; Where Z a and Z b The groups do not form a ring system.

2. The compound according to claim 1, comprising at least one structure of formula (I-1) to (I-6), preferably a compound of one of formula (I-1) to (I-6), The symbols Ar, Ar a ,Ar b ,Ar c ,Ar d , R a , R b and R c Having the definition given in claim 1.

3. The compound according to claim 1 or 2, characterized in that Ar a ,Ar b ,Ar c and / or Ar d The radicals are identical or different in each case and are selected from the group consisting of the formula (Ar a -1) to (Ar a -29) structure, The symbols used are as follows: Y is O, S or NR, preferably O or NR; k is independently 0 or 1 in each case; i is independently 0, 1 or 2 in each occurrence; j is independently 0, 1, 2 or 3 in each case; h is independently at each occurrence 0, 1, 2, 3 or 4; g is independently at each occurrence 0, 1, 2, 3, 4 or 5; R has the definition given above, in particular for claim 1, and the dashed key marks the connection point.

4. Compounds according to one or more of claims 1 to 3, characterized in that Ar a and / or Ar b The group is of formula -Ar e -Q structure, where Ar e are identical or different in each case and are a linked aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms and which may be substituted by one or more R groups; Ar e The arylene or heteroarylene radicals are preferably identical or different in each case and have 5 to 30 aromatic ring atoms and may be substituted by one or more R radicals, preferably selected from the group consisting of a benzene radical, a biphenyl radical, a terphenyl radical, a quaterphenyl radical, a fluorene radical, a spirobifluorene radical, a naphthalene radical, an indole radical, a benzofuranyl radical, a benzothiophene radical, a carbazole radical, a dibenzofuranyl radical, a dibenzothiophene radical, an indenocarbazole radical, an indolcarbazole radical, a pyridine radical, a pyrimidine radical, a pyrazine radical, a pyridazine radical, a triazine radical The invention relates to a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinazoline group, a quinoxaline group, a phenanthrene group or a terphenylidene group, each of which may be substituted with one or more R groups, and is preferably a phenyl group, a biphenyl group, a fluorene group, a dibenzofuran group, a terphenylidene group, a carbazole group or an indolocarbazole group; and Q is an electron transport group, preferably a pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, quinoline, isoquinoline, imidazole and / or benzimidazole group, which may be substituted with one or more R groups.

5. Compound according to one or more of claims 1 to 4, characterized in that Ar and / or Ar e The radicals are identical or different in each case and are selected from the group consisting of the formula (Ar e -1) to (Ar e -9) structure, The symbols used are as follows: j is independently 0, 1, 2 or 3 in each case; h is independently at each occurrence 0, 1, 2, 3 or 4; R has the definition given above, in particular for claim 1, and the dashed key marks the connection point.

6. Compound according to one or more of claims 1 to 3 and 5, characterized in that The compound comprises at least one structure of formula (I-2), wherein Ar a The group is selected from the formula (Ar a -1) to (Ar a -18) structure, wherein in the formula (Ar a -8) to (Ar a -12), the Y group is preferably O or NR, and Ar d The radicals are identical or different in each case and are selected from the group consisting of the formula (Ar a -1) to (Ar a -23) structure, wherein in the formula (Ar a -8) to (Ar a -12), the Y group is preferably O or NR, wherein Ar d The radicals are identical or different in each case and are preferably selected from the formula (Ar a -1)、(Ar a -2) and (Ar a -7) to (Ar a -18), and / or the compound comprises at least one structure of formula (I-4), wherein the Ar group is selected from the group consisting of e -1) to (Ar e -4) structure, Ar a The group is selected from the formula (Ar a -1) to (Ar a -18) structure, wherein in the formula (Ar a -8) to (Ar a -12), the Y group is preferably O or NR, and Ar d The radicals are identical or different in each case and are selected from the group consisting of the formula (Ar a -1) to (Ar a -23) structure, wherein in the formula (Ar a -8) to (Ar a -12), the Y group is preferably O or NR, wherein Ar d The radicals are identical or different in each case and are preferably selected from the formula (Ar a -1)、(Ar a -2), (Ar a -7) to (Ar a -18) structure.

7. Compound according to one or more of claims 1 to 3 and 5, characterized in that The compound comprises at least one structure of formula (I-3), wherein Ar c The radicals are identical or different in each case and are selected from the group consisting of the formula (Ar a -1) to (Ar a -23) structure, wherein in the formula (Ar a -8) to (Ar a -12) in the structure, the Y group is preferably O or NR, Ar c The radicals are preferably identical or different in each case and are selected from the group consisting of the formula (Ar a -1)、(Ar a -2), (Ar a -7) to (Ar a -18) structure; and Ar d The radicals are identical or different in each case and are selected from the group consisting of the formula (Ar a -1) to (Ar a -23) structure, wherein in the formula (Ar a -8) to (Ar a -12), the Y group is preferably O or NR, wherein Ar d The radicals are identical or different in each case and are preferably selected from the formula (Ar a -1)、(Ar a -2), (Ar a -7) to (Ar a -18), and / or the compound comprises at least one structure of formula (I-5) and / or formula (I-6), wherein the Ar groups are the same or different in each case and are selected from the group consisting of: e -1) to (Ar e -4) structure, Ar c The radicals are identical or different in each case and are selected from the group consisting of the formula (Ar a -1) to (Ar a -23) structure, wherein in the formula (Ar a -8) to (Ar a -12) in the structure, the Y group is preferably O or NR, Ar c The radicals are preferably identical or different in each case and are selected from the group consisting of the formula (Ar a -1)、(Ar a -2), (Ar a -7) to (Ar a -18) structure; and Ar d The radicals are identical or different in each case and are selected from the group consisting of the formula (Ar a -1) to (Ar a -18) structure, wherein in the formula (Ar a -8) to (Ar a -12), the Y group is preferably O or NR, wherein Ar d The radicals are identical or different in each case and are preferably selected from the formula (Ar a -1)、(Ar a -2), (Ar a -7) to (Ar a -18) structure.

8. The compound according to claim 4, characterized in that The compound comprises at least one structure of formula (I-2), wherein Ar a The group is of formula Ar e -Q structure, where the symbol Ar e and Q has the definition given in claim 5 and Ar d The radicals are identical or different in each case and are selected from the group consisting of the formula (Ar a -1) to (Ar a -23) structure, wherein in the formula (Ar a -8) to (Ar a -12), the Y group is preferably O or NR, wherein Ar d The radicals are identical or different in each case and are preferably selected from the formula (Ar a -1)、(Ar a -2), (Ar a -7) to (Ar a -18) and / or the compound comprises at least one structure of formula (I-4), wherein the Ar group is selected from the group consisting of e -1) to (Ar e -4) structure, Ar a The group is of formula Ar e -Q structure, where the symbol Ar e and Q has the definition given in claim 5 and Ar d The radicals are identical or different in each case and are selected from the group consisting of the formula (Ar a -1) to (Ar a -23) structure, wherein in the formula (Ar a -8) to (Ar a -12), the Y group is preferably O or NR, wherein Ar d The radicals are identical or different in each case and are preferably selected from the formula (Ar a -1)、(Ar a -2), (Ar a -7) to (Ar a -18) structure.

9. Compounds according to one or more of claims 1 to 5, characterized in that The compound comprises at least one structure of formula (I-1) and / or formula (I-2), wherein Ar a The group contains an electron transport group or is an electron transport group, wherein Ar a The radical preferably comprises a pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, quinoline, isoquinoline, imidazole and / or benzimidazole radical or is one of the radicals mentioned, where these radicals may be substituted by one or more R radicals, with particular preference being given to triazine radicals.

10. The compound according to claim 9, characterized in that The compound comprises at least one structure of formula (I-1), wherein Ar b The group contains an electron transport group or is an electron transport group, wherein Ar a The radical preferably comprises a pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, quinoline, isoquinoline, imidazole and / or benzimidazole radical or is one of the radicals mentioned, where these radicals may be substituted by one or more R radicals, with particular preference being given to triazine radicals.

11. The compound according to claim 9, characterized in that The compound comprises at least one structure of formula (I-1), wherein Ar b The group is selected from the formula (Ar a -1) to (Ar a -18) structure, wherein in the formula (Ar a -8) to (Ar a -12), the Y group is preferably O or NR; wherein Ar a The group is preferably of the formula Ar e -Q structure, where the symbol Ar e and Q has the definition given in claim 5.

12. A compound according to one or more of claims 1 to 11, comprising at least one structure of formula (II-1) to (II-154), preferably a compound of one of formula (II-1) to (II-154), The symbols R and R a , R b and R c The definitions given in claim 1 are as follows, and the other symbols are as follows: X is the same or different in each instance and is N, CR, or if a group is attached to the structure, X is C; and Y is O, S, NR or C(R)2, preferably O, NR or C(R)2.

13. A compound according to one or more of claims 1 to 12, comprising at least one structure of formula (III-1) to (III-60), preferably a compound of one of formula (III-1) to (III-60), The symbols R and R a , R b and R c The definitions given in claim 1 are as follows, and the symbols used are as follows: Y is O, S, NR or C(R)2, preferably O, NR or C(R)2; i is independently 0, 1 or 2 in each occurrence; j is independently 0, 1, 2 or 3 in each case; h is independently at each occurrence 0, 1, 2, 3 or 4; g is independently 0, 1, 2, 3, 4 or 5 at each occurrence.

14. An oligomer, polymer or dendrimer comprising one or more compounds according to any one of claims 1 to 13, wherein: One or more bonds of the compound to the polymer, oligomer or dendrimer are present in place of a hydrogen atom or a substituent.

15. A preparation comprising at least one compound according to one or more of claims 1 to 13 or an oligomer, polymer or dendrimer according to claim 14 and at least one further compound, wherein the further compound is preferably selected from one or more solvents.

16. A composition comprising at least one compound according to one or more of claims 1 to 13 or an oligomer, polymer or dendrimer according to claim 14 and at least one further compound selected from fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF, host materials, electron transport materials, electron injection materials, hole conducting materials, hole injection materials, electron blocking materials and hole blocking materials, preferably host materials.

17. A process for preparing a compound according to one or more of claims 1 to 13, characterized in that A phenyl compound fused with a cyclopentyl group is synthesized, and at least one aromatic or heteroaromatic group is introduced, preferably by means of a nucleophilic aromatic substitution reaction or a coupling reaction.

18. Use of a compound according to one or more of claims 1 to 13 or an oligomer, polymer or dendrimer according to claim 14 in electronic devices, preferably as host material, electron transport material, electron injection material, hole conducting material, hole injection material, electron blocking material, hole blocking material.

19. An electronic device comprising at least one compound according to one or more of claims 1 to 13 or an oligomer, polymer or dendrimer according to claim 14.

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