Silicon compounds for organic electroluminescent devices

Abstract

The invention relates to silicon and germanium compounds with special aromatic substituents for use in electronic devices, in particular in organic electroluminescent devices, and to electronic devices, in particular organic electroluminescent devices, which contain these OLED materials.

Description

[0001] Foreignfiling_text P24-256.docx

[0002] - 1 -

[0003] Silicon compounds for organic electroluminescence devices

[0004] The present invention relates to silicon and germanium compounds 5 with special aromatic substituents for use in electronic devices, in particular in organic electroluminescent devices, and to electronic devices, in particular organic electroluminescent devices, containing these OLED materials.

[0005] 10

[0006] Electroluminescent devices often comprise additional layers besides an emission layer, 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. These layers have a significant influence on the performance of electroluminescent devices. Generally, there is still room for improvement in the materials used, particularly with regard to efficiency, but also with regard to the device's lifetime.

[0007] The object of the present invention is to provide compounds suitable for use in an organic electronic device, in particular an organic electroluminescence device, and which, when used in this device, lead to good device properties, as well as to provide the corresponding electronic device. In particular, the object of the present invention is to provide compounds that lead to good efficiency and a long lifetime. In addition to the emitters, hole transport materials, hole injection materials, electron blocking materials, electron injection materials, electron transport materials, and hole blocking materials contribute to these properties. Furthermore, the properties of the matrix materials, also referred to as host materials, have a significant influence on the lifetime and efficiency of the organic electroluminescence device.Foreignfiling_text P24-256.docx.

[0008] -2 -

[0009] Furthermore, it is an object of the present invention to provide compounds which are characterized by a low refractive index (RI).

[0010] 5 Another task can be seen as providing electronic devices with excellent performance as cost-effectively as possible and in consistent quality.

[0011] Furthermore, the electronic devices should be usable or adaptable for many purposes. In particular, the performance of the electronic devices should be maintained over a wide temperature range.

[0012] Surprisingly, it was found that certain compounds, described in more detail below, solve this problem, are well suited for use in electroluminescent devices, and lead to organic electroluminescent devices that exhibit very good properties, particularly with regard to lifetime, color purity, and efficiency. These compounds, as well as electronic devices, especially organic electroluminescent devices (20), which contain such compounds, are therefore the subject of the present invention.

[0013] The subject of the invention is a compound of formula (I),

[0014] 25 R 4

[0015] R 1 -M— R 3

[0016] R 2 Formula (I)

[0017] 30 where the following applies to the symbols:

[0018] M is Si or Ge;

[0019] R 1 , R 2 , R 3 and R 4The structure is either a straight-chain alkyl group with 1 to 40 carbon atoms, a branched alkyl group with 3 to 40 carbon atoms, or a cyclic alkyl group, either the same or different in each occurrence. Foreignfiling_text P24-256.docx

[0020] - 3 -

[0021] group with 5 to 40 C atoms, each of which may be substituted with one or more R' and / or Si(R')₃ substituents, where two or more R substituents 1 , R 2 , R 3 and R 4can also form mono-, bi- and tricyclic rings with each other; a non-condensed aromatic ring system with 6 to 60 aromatic ring atoms or a heteroaromatic ring system with 5 to 60 aromatic ring atoms, which contains at least one heteroatom selected from O and S, preferably an O atom, wherein the aromatic or heteroaromatic ring system can be substituted with one or more R" substituents, an aralkyl group with 7 to 60 carbon atoms, which can also be substituted with one or more R" substituents, or OSi(R')₃; wherein two or more of the R substituents can be 1 , R 2 , R 3 and R 4 be linked together, preferably by a single bond, 15 an O atom or a CR₂ group, and thereby form a ring system, preferably a mono-, bi- or tricyclic ring;

[0022] with the proviso that at least one of the residues R 1 , R 2 , R 3 and R4 the following formula (a) corresponds

[0023] 20

[0024] 25

[0025]

[0026] where the dashed line represents the connection to M of formula (I);

[0027] R is the same or different in each occurrence, a tert-Alky I- 30

[0028] a group with 4 to 40 C atoms or a neo-alkyl group with 5 to 40 C atoms, wherein these groups may each be substituted with one or more D and / or F atoms, a tertiary aralkyl group with 9 to 40 C atoms, which may also be substituted with one or more R" residues, or a 35

[0029] Si(R')3 group; Foreignfiling_text P24-256.docx

[0030] -4 -

[0031] R' is, in each occurrence, either a straight-chain alkyl group with 1 to 40, preferably 1 to 20, carbon atoms, a branched alkyl group with 3 to 40, preferably 3 to 20, carbon atoms, or a cyclic alkyl group with 5 to 40, preferably 5 to 20, carbon atoms, wherein two R' groups bonding to the same Si atom may also form rings, or an aryl group Ar with 6 to 20 carbon atoms, wherein the aryl group Ar may be substituted with one or more substituents selected from straight-chain alkyl groups with 1 to 20 carbon atoms, branched alkyl groups with 3 to 10 to 20 carbon atoms, or cyclic alkyl groups with 5 to 20 carbon atoms;

[0032] R" is the same or different at each occurrence and is chosen from the group consisting of R', H, D, F, CN and Si(Alkyl)₃, 15 where alkyl is the same or different at each occurrence for an alkyl group with 1 to 10 C atoms;

[0033] R ais the same or different H, D, F or an alkyl group with 1 to 40 C atoms, which may be substituted with one or more 20 F atoms, an aryl group Ar with 6 to 40 C atoms or an OSi(R')₃ group, wherein the aryl group Ar may be substituted with one or more substituents selected from straight-chain alkyl groups with 1 to 20 C atoms, branched alkyl groups with 3 to 20 C atoms or cyclic alkyl groups with 5 to 20 C atoms; two R groups may also be substituted a different residues of formula (1a) are linked together, preferably by a single bond, by an O atom or a CR₂ group;

[0034] 30 R b is H, D, F, CN, an alkyl group with 1 to 40 C atoms, an aryl group Ar with 6 to 40 C atoms or an OSi(R')₃ group.

[0035] An aryl group according to the present invention contains 6 to 40 carbon atoms; a heteroaryl group according to this invention contains 3 to 40 carbon atoms and at least one heteroatom, provided that the sum of the carbon atoms and heteroatoms is at least 5. The heteroatoms Foreignfiling_text P24-256.docx

[0036] - 5 -

[0037] The groups are selected from O and / or S. An aryl group or heteroaryl group is understood to be either a simple aromatic cycle, i.e., benzene, or a simple heteroaromatic cycle, for example, furan, thiophene, etc., or a fused (fused) aryl or heteroaryl group, for example, naphthalene, anthracene, phenanthrene, dibenzofuran, dibenzothiophene, etc. Aromatic compounds linked together by single bonds, such as biphenyl, are not referred to as aryl or heteroaryl groups, but rather as aromatic ring systems.

[0038] 10

[0039] An aromatic ring system according to the present invention contains 6 to 60 carbon atoms in the ring system, preferably 6 to 40 carbon atoms in the ring system. A heteroaromatic ring system according to this invention contains 3 to 60 carbon atoms, 3 to 40 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 heteroatoms are selected from oxygen and / or sulfur. An aromatic or heteroaromatic ring system according to the present invention is understood to be a system that does not necessarily contain only aryl or heteroaryl groups, but in which several aryl or heteroaryl groups may also be linked by a non-aromatic unit, such as a carbon, sulfur, or oxygen atom. This includes systems such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, diaryl ether, stilbene, etc.as aromatic ring systems within the meaning of the present invention 25, and likewise systems in which two or more aryl groups are connected, for example, by a short alkyl group. Preferably, the aromatic ring system is selected from fluorene, 9,9'-spirobifluorene, or groups in which two or more aryl and / or heteroaryl groups are linked to one another by single bonds.

[0040] 30

[0041] An alkyl group within the meaning of the present invention can be linear, branched, or cyclic. Within the scope of the present invention, an aliphatic hydrocarbon residue or an alkyl group or an alkenyl or alkynyl group containing 1 to 20 carbon atoms, and in which individual hydrogen atoms or CH2 groups can also be substituted by the aforementioned groups, preferably the residues methyl, Foreignfiling_text P24-256.docx

[0042] - 6 -

[0043] Ethyl, n-Propyl, i-Propyl, n-Butyl, i-Butyl, s-Butyl, t-Butyl, 2-Methylbutyl, n- Pentyl, s-Pentyl, neo-Pentyl, Cyclopentyl, n-Hexyl, neo-Hexyl, Cyclohexyl, n-Heptyl, Cycloheptyl, n-Octyl, Cyclooctyl, 2-Ethylhexyl, Trifluormethyl, Pentafluorethyl, 2,2,2-Trifluorethyl, Ethenyl, Propenyl, Butenyl, Pentenyl, 5 Cyclopentenyl, Hexenyl, Cyclohexenyl, Heptenyl, Cycloheptenyl, Octenyl, Cyclooctenyl, Ethinyl, Propinyl, Butinyl, Pentinyl, Hexinyl, Heptinyl oder Octinyl verstanden. Unter einer Alkoxygruppe mit 1 bis 40 C-Atomen werden bevorzugt Methoxy, Trifluormethoxy, Ethoxy, n-Propoxy, i-Propoxy, n-Butoxy, i-Butoxy, s-Butoxy, t-Butoxy, n-Pentoxy, s-Pentoxy, 2-Methyl- 10 butoxy, n-Hexoxy, Cyclohexyloxy, n-Heptoxy, Cycloheptyloxy, n-Octyloxy, Cyclooctyloxy, 2-Ethylhexyloxy, Pentafluorethoxy und 2,2,2-Trifluorethoxy verstanden.A thioalkyl group with 1 to 40 carbon atoms includes, in particular, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, 1-butylthio, s-butylthio, t-butylthio, n-pentylthio, s-pentylthio, n-hexylthio, 15 Cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, Cyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthio, cyclooctenylthio, ethynylthio, propynylthio, Butynylthio, pentynylthio, 20 hexynylthio, heptynylthio or octynylthio are understood. In general, alkyl, alkoxy or thioalkyl groups according to the present invention can be straight-chain, branched or cyclic, wherein one or more non-adjacent CH₂ groups can be replaced by the groups mentioned above; furthermore, one or more H atoms can also be replaced by D or F, 25 preferably F.

[0044] An aralkyl group within the meaning of the present invention is understood to be an alkyl group which is substituted with an aryl group and which is bonded via the alkyl group, such as, for example, in the simplest case 30, a benzyl group.

[0045] An aromatic or heteroaromatic ring system with 5 to 60 or 5 to 40 aromatic ring atoms, respectively, which may be further substituted with the aforementioned substituents and which may be linked via any 35 positions on the aromatic or heteroaromatic compound, is understood to include, in particular, groups derived from benzene.

[0046] - 7 -

[0047] Naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, preferably dibenzofuran and dibenzothiophene, particularly preferably dibenzofuran, or groups derived from combinations of these systems.

[0048] 10. In the context of this description, the phrase "two or more residues can form a ring" means, among other things, that the two residues are linked to each other by a chemical bond involving the formal elimination of two hydrogen atoms. This is illustrated by the following scheme.

[0049] 15

[0050] Ring formation

[0051] the remains R

[0052]

[0053] 20

[0054] Furthermore, the above formulation should also be understood to mean that if one of the two residues represents hydrogen, the second residue binds to the position to which the hydrogen atom was bonded, forming a ring. This is to be understood by the 25

[0055] The following scheme can be illustrated:

[0056] Ring formation of the residues R

[0057]

[0058] 30

[0059]

[0060] A tertiary alkyl group or tert-alkyl group within the meaning of the present invention, as defined by R, is an alkyl group that is bonded to the phenyl ring in formula (1a) via a tertiary carbon atom, i.e., a carbon atom bonded to three other carbon atoms. The alkyl group can also be cyclic, so that Foreignfiling_text P24-256.docx

[0061] - 8 -

[0062] For example, 1-methylcyclopentyl is a tertiary alkyl group within the meaning of the present invention. A neo-alkyl group within the meaning of the present invention is an alkyl group that is bonded to the phenyl ring in formula (1a) via a carbon atom, wherein a tertiary alkyl group 5 is bonded to this carbon atom. An example of the simplest neo-alkyl group is a neo-pentyl group having the formula (CH₃)₃C-CH₂-. A tertiary aralkyl group within the meaning of the present invention is an aralkyl group that is bonded to the phenyl ring in formula (1a) via a tertiary carbon atom, in particular a phenyl-C(alkyl)₂- group, wherein alkyl 10 represents an alkyl group with 1 to 10 carbon atoms, and the phenyl group may be further substituted by one or more R" groups.

[0063] Examples of suitable and preferred tert-alkyl groups are the

[0064] 15 following groups:

[0065] 20

[0066]

[0067] Examples of suitable and preferred neo-alkyl groups are the following groups:

[0068] 25

[0069]

[0070] 30

[0071] Examples of suitable and preferred tertiary aralkyl groups are the following groups:

[0072] 35 Foreignfiling_text P24-256.docx

[0073] - 9 -

[0074] 5

[0075]

[0076] In these structures, the dashed line indicates the connection between the groups.

[0077] 10 Furthermore, it may be provided that the compound has exactly one Si atom or exactly one Ge atom, or that the compound has exactly two Si atoms, exactly two Ge atoms, or exactly one Si atom and exactly one Ge atom.

[0078] 15 In one embodiment, the compounds of formula (I) are characterized in that one, two, three or four of the residues R 1 , R 2 , R 3 and R 4 , preferably two, three or four of the residues R 1 , R 2 , R 3 and R 4 and especially preferentially all four residues R 1 , R 2 , R 3 and R 4 correspond to formula (1a).

[0079] 20

[0080] In a further preferred embodiment of the present invention, the compounds of formula (I) are characterized in that they have a molecular weight of ≥ 700 g / mol, preferably of ≥ 750 g / mol, particularly preferably of ≥ 850 g / mol and particularly of ≥ 900 g / mol 25.

[0081] In a further preferred embodiment of the present invention, the compound of formula (I) corresponds to one of the following formulas (Ha) to (Ild),

[0082] 30

[0083] 35 Foreignfiling_text P24-256.docx

[0084] - 10 -

[0085] 5

[0086]

[0087] 10

[0088]

[0089] Formula (lib)

[0090] 15

[0091] 20

[0092]

[0093] Formula (llc) Formula (lld)

[0094] where the symbols are the 25 mentioned above in relation to formulas (I) and (1a).

[0095] have meanings.

[0096] In a further preferred embodiment of the present invention, M stands for Si in the compounds of formula (I) or the preferred embodiments.

[0097] 30

[0098] In a further preferred embodiment of the present invention, the compounds of formula (I) are characterized in that one, two or three of the groups R 1 , R2 , R 3 and R 4 In each occurrence, either the same or different, a methyl group, an ethyl group, an isopropyl group 35

[0099] group, a tert-butyl group, a 1-adamantyl group, a neo-pentyl group Foreignfiling_text P24-256.docx

[0100] - 11 -

[0101] group, an unsubstituted phenyl group or a phenyl group substituted with one or more R" residues.

[0102] In a further preferred embodiment of the present invention 5, the compounds of formula (I) are characterized in that R, in each occurrence, is either a tert-butyl group, a 1-adamantyl group, a neo-pentyl group or a trimethylsilyl group.

[0103] 10 In a further preferred embodiment of the present invention, the compounds of formula (I) are characterized in that R aThe condition is the same or different H, D or F, preferably H, in each instance.

[0104] In a further preferred embodiment of the present invention 15, the compounds of formula (I) are characterized in that R b The group is either the same or different in each occurrence: H, D, F, CN or a methyl group, preferably H.

[0105] In a particularly preferred embodiment of the present

[0106] 20. The invention corresponds to the remainder of formula (1a) of one of the following formulas (1b) or (1c)

[0107] 25

[0108]

[0109] Formula (Ib) Formula (Ic)

[0110] 30

[0111] where the dashed line denotes the bond to M and R 5 , R 6 and R 7in each occurrence, whether the group is a linear, branched or cyclic alkyl group with 1 to 15 carbon atoms, preferably with 1 to 5 carbon atoms and particularly preferably with 1 carbon atom, or that 35 is one of the R groups. 5 , R 6 and R 7 , which bind to the same C or Si atom, represents a phenyl group which is linked to one or more R substituents. Foreignfiling_text P24-256.docx

[0112] - 12 -

[0113] can be substituted and the other two of the residues R 5 , R 6 and R 7 , which bond to the same C or Si atom, whether identical or different in each occurrence, represent a linear, branched, or cyclic alkyl group with 1 to 15 C atoms; two or three of the R groups can also be 5 , R 6 5 and R 7 , which bind to the same C or Si atom, forming a mono-, bi- or tricyclic group.

[0114] In a particularly preferred embodiment of the present invention, the compound of formula (I) corresponds to one of the following 10 formulas (IIa1) to (IId1)

[0115] 15

[0116]

[0117] Formula (IIa1) Formula (IIb1)

[0118] 20

[0119] 25

[0120]

[0121] Formula (IIc1) Formula (IId1)

[0122] 30

[0123] the symbols have the meanings mentioned above in relation to formula (I) and (1a).

[0124] In a preferred embodiment of the invention, the tertiary 35

[0125] Alkyl group or the tertiary aralkyl group R in formula (1a) or the group -CR 5 R 6 R 7 In formula (Ib) a structure according to one of the formulas Foreignfiling_text P24-256.docx

[0126] - 13 -

[0127] (RC-1) to (RC-7), each of which can also be substituted by D or F, with structures (RC-1), (RC-2) and (RC-6) being preferred:

[0128] 5

[0129]

[0130] Formula (RC-1) Formula (RC-2) Formula (RC-3) Formula (RC-4)

[0131] 10

[0132]

[0133] Formula (RC-5) Formula (RC-6) Formula (RC-7)

[0134] 15

[0135] where the dashed bond represents the attachment point to the phenyl ring in formula (1a) or (1b) and A' represents an alkyl group with 1 to 10 C atoms, preferably with 1 to 5 C atoms or a phenyl group which may also be substituted by one or more R" groups.

[0136] 20

[0137] Furthermore, it may be provided that at least one remainder R 1 , R 2 , R 3 and / or R 4The compound, whether the same or different at each occurrence, is selected from phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, benzofuran, benzothiophene, dibenzofuran or dibenzothiophene, each of which may be substituted with one or more R" residues.

[0138] 25

[0139] If the compound according to the invention contains aromatic or heteroaromatic groups R 1 , R 2 , R 3 and / or R 4 in an embodiment it is preferred if these do not contain heteroaryl groups with more than two directly fused aromatic six-membered rings 30

[0140] They exhibit a particularly strong preference for substituents that do not contain any heteroaryl groups with directly fused six-membered rings. This preference is due to the low triplet energy of such structures.

[0141] 35

[0142] The groups R 1 , R2 , R 3 and / or R 4 , if these represent an aryl group or heteroaryl group, are preferably the same or different in each Foreignfiling_text P24-256.docx

[0143] - 14 -

[0144] The occurrence selected is from the group consisting of the groups of the following formulas Ar-1 to Ar-34,

[0145] 5

[0146]

[0147] Ar-1 Ar-2 Ar-3 Ar-4

[0148] 10

[0149]

[0150] 15

[0151] 20

[0152]

[0153] 25

[0154]

[0155] 30

[0156]

[0157] 35 Foreignfiling_text P24-256.docx

[0158] - 15 -

[0159] 5 Ar-17

[0160] 10

[0161] 15

[0162] 20

[0163] Ar-22 25

[0164] 30 Ar-23 Ar-24

[0165] 35

[0166]

[0167] Ar-26 Foreignfiling_text P24-256.docx

[0168] - 16 -

[0169] 5

[0170] 10

[0171]

[0172] 15 Ar-31

[0173] 20

[0174]

[0175] Ar-32 Ar-33 Ar-34

[0176] 25 where R" has the meanings mentioned above, the dashed line represents the connection to the corresponding group and furthermore:

[0177] Ar 1In each occurrence, a bivalent aromatic ring system with 6 to 18 aromatic ring atoms or a heteroaromatic ring system with 5 to 18 aromatic ring atoms, which contains at least one heteroatom selected from O and S, preferably one heteroatom selected from O and S, particularly preferably one O atom, wherein the aromatic and heteroaromatic ring systems are each equipped with one or more R groups. 1 can be substituted; Foreignfiling_text P24-256.docx

[0178] - 17 -

[0179] A is the same or different from C(R")2, O or S in each occurrence;

[0180] p is either 0 or 1, where p = 0 means that the group Ar 1 not present 5 and that the corresponding aromatic or heteroaromatic group is directly bonded to the corresponding residue.

[0181] Structures of the formulas (Ar-1 ), (Ar-2), (Ar-3) and (Ar-4) are preferred.

[0182] 10

[0183] The structures Ar-1 to Ar-34 shown above are also preferred embodiments for the Ar group, wherein in this case the R" groups represent H, D or an alkyl group with 1 to 20 C atoms, preferably with 1 to 10 C atoms and particularly preferably with 1 to 5 C atoms.

[0184] 15

[0185] If the above-mentioned groups for structures of formulas (Ar-1) to (Ar-34) have several groups A, then all combinations from the definition of A are possible.

[0186] 20. If A stands for C(R")2, the substituents R" bonded to this carbon atom, preferably the same or different in each instance, represent a linear alkyl group with 1 to 10 carbon atoms, or a branched or cyclic alkyl group with 3 to 10 carbon atoms, or an aryl group with 6 to 20 carbon atoms, which may be substituted with one or more 25 substituents selected from straight-chain alkyl groups with 1 to 20 carbon atoms, branched alkyl groups with 3 to 20 carbon atoms, or cyclic alkyl groups with 5 to 20 carbon atoms. R" particularly preferably represents a methyl group or a phenyl group. The R" groups may also form a ring system with each other, which 30 leads to a spiro system.

[0187] In the compounds according to the invention, which are processed by vacuum evaporation, the alkyl groups preferably have no more than ten carbon atoms, particularly preferably no more than six carbon atoms, and most preferably no more than five carbon atoms. For compounds processed from solution, compounds containing Foreignfiling_text P24-256.docx are also suitable.

[0188] - 18 -

[0189] Alkyl groups, especially branched alkyl groups, are substituted with up to 10 carbon atoms or are substituted with oligoarylene groups, for example ortho-, meta-, para- or branched terphenyl or quaterphenyl groups.

[0190] 5

[0191] Another object of the present invention is a combination of formula (IIIa) and (IIIlb),

[0192] R 3 R 1

[0193] 109I I9

[0194] R 2 -M - M— R 2

[0195] R 1 R 3 Formula (IIIa)

[0196] 15 X MM

[0197]

[0198] R 2 R Formula (IIIb)

[0199] where the symbols have the meanings mentioned in relation to formula (I), the dashed line represents any group of connections 20 and at least one of the residues R 1 , R 2 and R 3 in formula (IIIa) or

[0200] at least one of the residues R 1 or R 2 in formula (IIIb) represents a group of formula (1a).

[0201] In a first preferred embodiment of formula (IIIa), the dashed line is a single bond and the compound of formula (IIIa) corresponds to the following formula (IIIa1):

[0202] R 3 R 1

[0203] R 2 -M - M— R 2

[0204] 30 | |

[0205]

[0206] R 1 R 3 Formula (IIIa1)

[0207] In a second preferred embodiment of formula (IIIa), the dashed line is an alkylene group and the compound of formula (IIIa) 35 corresponds to the following formula (IIIa2): Foreignfiling_text P24-256.docx

[0208] - 19 -

[0209]

[0210] Formula (IIIa2)

[0211] 5

[0212] where the following applies to the symbols and indices:

[0213] R 8 is the same or different in each occurrence H, D, F, a straight-chain alkyl group with 1 to 10 C atoms or a branched alkyl group with 3 to 10 C atoms, wherein two R groups 8 also together 10

[0214] can form a ring; and

[0215] n is 1, 2, 3, 4, 5 or 6; preferably 2.

[0216] In a first preferred embodiment of formula (IIIb), the dashed lines each represent an alkylene group, and the compound of 15

[0217] Formula (IIIb) corresponds to the following formula (IIIb1):

[0218] 20

[0219]

[0220] o Formula (IIIb1)

[0221] 25 where the following applies to the symbols and indices:

[0222] R 8 is the same or different in each occurrence H, D, F, a straight-chain alkyl group with 1 to 10 C atoms or a branched alkyl group with 3 to 10 C atoms, wherein two R groups 8 can also form a ring with each other;

[0223] 30 n is 1, 2 or 3; preferably 2;

[0224] o is 1, 2 or 3; preferably 2.

[0225] In a second preferred embodiment of formula (IIIb), the dashed lines each represent an alkenyl group, and the compound of formula (IIIb) corresponds to the following formula (IIIb2): Foreignfiling_text P24-256.docx

[0226] - 20 -

[0227] 5

[0228]

[0229] Formula (IIIb2)

[0230] where the following applies to the symbols:

[0231] R 8 is the same or different in each occurrence H, D, F, a straight-chain alkyl group with 1 to 10 C atoms, a branched alkyl group with 10³ to 10 C atoms, an aromatic ring system with 6 to 18 aromatic ring atoms or a heteroaromatic ring system with 5 to 18 aromatic ring atoms, wherein two R groups 8 They can also form a ring together.

[0232] 15 In a third preferred embodiment of formula (IIIb), the dashed lines each represent a group of arias and the combination of formula (IIIb) corresponds to the following formula (IIIb3):

[0233] 20

[0234] 25

[0235]

[0236] (R 8 )n Formula (IIIb3)

[0237] where the following applies to the symbols and indices:

[0238] 30 R 8 is the same or different in each occurrence D, F, a straight-chain alkyl group with 1 to 10 C atoms, a branched alkyl group with 3 to 10 C atoms, an aromatic ring system with 6 to 18 aromatic ring atoms or a heteroaromatic ring system with 5 to 18 aromatic ring atoms, wherein two R groups 8 can also form a ring 35 together; and

[0239] n is 0, 1, 2, 3 or 4, preferably 0 or 2. Foreignfiling_text P24-256.docx

[0240] -21 -

[0241] Furthermore, the compounds may include crosslinkable groups Q. A crosslinkable group Q, as used in the present invention, is a functional group capable of undergoing a reaction 5 to form an insoluble compound. This reaction can occur with another identical group Q, another different group Q, or any other part of the same or a different compound. The crosslinkable group is thus a reactive group. The reaction 10 of the crosslinkable group results in a correspondingly crosslinked compound. The chemical reaction can also be carried out within the layer, forming an insoluble layer. Crosslinking can usually be accelerated by heat or by UV, microwave, X-ray, or electron radiation, optionally in the presence 15 of an initiator.“Insoluble” within the meaning of the present invention preferably means that the compound according to the invention, after the crosslinking reaction, i.e., after the reaction of the crosslinkable groups, has a solubility at room temperature in an organic solvent that is at least a factor of 3, preferably at least a factor of 10, lower than that of the corresponding, non-crosslinked compound according to the invention in the same organic solvent.

[0242] The compound according to formula (I) or preferred embodiments of this formula may comprise one, two, three or more crosslinkable groups Q, wherein the compound according to formula (I) or preferred embodiments of this formula preferably comprises two, three or more crosslinkable groups Q.

[0243] According to the invention, preferred networkable groups Q are those in

[0244] 30

[0245] The following groups are listed:

[0246] a) Terminal or cyclic alkenyl or terminal dienyl and alkynyl groups:

[0247] Suitable units are those that have a terminal or cyclic double35

[0248] bond, a terminal dienyl group or a terminal triple bond, in particular terminal or cyclic Foreignfiling_text P24-256.docx

[0249] -22 -

[0250] Alkenyl-terminal dienyl or terminal alkynyl groups with 2 to 40 carbon atoms, preferably with 2 to 10 carbon atoms, wherein individual CH2 groups and / or individual hydrogen atoms can also be replaced by the aforementioned groups R. Furthermore, groups 5, which can be considered precursors and which are capable of forming a double or triple bond in situ, are also suitable.

[0251] b) Alkenyloxy, dienyloxy or alkynyloxy groups:

[0252] Alkenyloxy, dienyloxy or alkynyloxy groups are also suitable, preferably alkenyloxy groups.

[0253] c) Acrylic acid groups:

[0254] Acrylic acid units in the broadest sense are also suitable, preferably acrylic esters, acrylamides, methacryl esters and methacrylamides. C₁₋₁₀-alkyl acrylate and C₁₋₁₀-alkyl methacrylate are particularly preferred.

[0255] The crosslinking reaction of the groups mentioned above under a) to c) can occur via a radical, a cationic or anionic mechanism, but also via cycloaddition.

[0256] It can be advantageous to add a suitable initiator for the crosslinking reaction. Suitable initiators for radical crosslinking include dibenzoyl peroxide, AIBN 25, or TEMPO. Suitable initiators for cationic crosslinking include AlCl₃, BF₃, triphenyl methyl perchlorate, or tropylium hexachloroantimonate. Suitable initiators for anionic crosslinking are bases, especially butyllithium.

[0257] 30 In a preferred embodiment of the present invention, however, the crosslinking is carried out without the addition of an initiator and is initiated exclusively thermally. This preference is justified by the fact that the absence of the initiator prevents impurities in the layer that could lead to a deterioration of the device properties. 35 Foreignfiling_text P24-256.docx

[0258] -23 -

[0259] d) Oxetanes and oxiranes:

[0260] Another suitable class of crosslinkable groups Q are oxetanes and oxiranes, which crosslink cationically by ring opening.

[0261] 5. It can be advantageous to add a suitable initiator for the crosslinking reaction. Suitable initiators include, for example, AlCl₃, BF₃, triphenylmethyl perchlorate, or tropylium hexachloroantimonate. Photoacids can also be added as initiators.

[0262] 10

[0263] e) Silanes:

[0264] Silane groups SiRs are also suitable as a class of crosslinkable groups, where at least two groups R, preferably all three groups R, represent CI or an alkoxy group with 1 to 20 carbon atoms. This group reacts in the presence of water to form an oligo- or polysiloxane.

[0265] f) Cyclobutane groups

[0266] 20 The crosslinkable groups Q mentioned above under a) to f) are generally known to the person skilled in the art, as are the suitable reaction conditions used to react these groups.

[0267] Preferred crosslinkable groups Q comprise alkenyl groups of the

[0268] 25 following formula Q1, dienyl groups of the following formula Q2, alkynyl groups of the following formula Q3, alkenyloxy groups of the following formula Q4, dienyloxy groups of the following formulas Q5, alkynyloxy groups of the following formula Q6, acrylic acid groups of the following formulas Q7 and Q8, oxetane groups of the following formulas Q9, Q30 and Q10, oxirane groups of the following formula Q11, cyclobutane groups of the following formulas Q12, Q13 and Q14:

[0269] 35

[0270]

[0271] Foreignfiling_text P24-256.docx

[0272] - 24 -

[0273] 5

[0274] 10

[0275] 15

[0276] 20

[0277] 25

[0278] 30

[0279]

[0280] The remains R 11 , R 12 , R 13 and R 14 In formulas Q1 to Q8, Q11, Q13 and Q14, H, a straight-chain or branched alkyl group with 1 to 6 carbon atoms, preferably 1 35, occurs in each instance, whether identical or different.

[0281] up to 4 carbon atoms. The R atoms are particularly favored. 11 , R 12 , R 13 and R 14 H, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl or tert-buty I and Foreignfiling_text P24-256.docx

[0282] -25 -

[0283] H or methyl are particularly favored. The indices used have the following meanings: m = 0 to 8; and n = 1 to 8. Ar 10 In formula Q14, the same meanings can be assumed as Ar' in formula (I).

[0284] 5 The dashed bonds in formulas Q1 to Q11 and Q14, as well as the dashed bonds in formulas Q12 and Q13, represent the connection of the crosslinkable group to the repeating units.

[0285] The crosslinkable groups of formulas Q1 to Q14 can be directly linked to 10 of the repeating unit, or indirectly, via another mono- or polycyclic aromatic or heteroaromatic ring system Ar 10 , as shown in the following formulas Q15 to Q28:

[0286] 15

[0287] 20

[0288] 25

[0289] 30

[0290]

[0291] 35 Foreignfiling_text P24-256.docx

[0292] - 26 -

[0293] 5

[0294] 10

[0295] 15

[0296]

[0297] where Ar 10in formulas Q15 to Q28 the same meanings 20 can take on as Ar' in formula (I).

[0298] The following are particularly preferred networkable groups Q:

[0299] HH

[0300] H

[0301] 25

[0302] -(CH2) m ^ (CH2) m ^^

[0303] Q1a Q2a

[0304] 0

[0305] R 11

[0306] 30

[0307] H

[0308] -(CH2) m — Q_(CH2) n ^ H

[0309] ....... (CH2) m

[0310] 35

[0311]

[0312] Q4a Q7a Foreignfiling_text P24-256.docx

[0313] -27 -

[0314] 5

[0315] 10

[0316] 15

[0317] 20

[0318] 25

[0319] 30

[0320]

[0321] 35 Foreignfiling_text P24-256.docx

[0322] - 28 -

[0323] 5

[0324]

[0325] The remains R 11 , R 12 , R 13 and R 14 Each occurrence, whether identical or different, consists of H or a straight-chain or branched alkyl group with 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms. The R groups are particularly preferred. 11 , R 12 , R 13 and R 14 Methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl or tert-butyl, and especially methyl.

[0326] 15 The indices used have the following meaning: m = 0 to 8 and n = 1 to 8.

[0327] The following are particularly preferred networkable groups Q:

[0328] HH

[0329] 20

[0330] H

[0331] — H

[0332] Q1b Q1c

[0333] H

[0334] 25 H

[0335] Q2b Q2c

[0336] H o

[0337] 30 u

[0338] O' \ H.'0—' H H

[0339]

[0340] Q4b Q7c

[0341] 35 Foreignfiling_text P24-256.docx

[0342] -29 -

[0343] 0

[0344] 0 \ H X CH 2X / H , C >=< H, CH 2 5

[0345] Q7d Q12a

[0346] H H

[0347] \ / H

[0348] I H

[0349] t O'

[0350] 10

[0351] Q13a Q14b

[0352] H

[0353] H

[0354] — H

[0355] 15

[0356] Q15b Q15c

[0357] H H H

[0358] j H

[0359] 20

[0360] Q15d Q15e

[0361] H

[0362] 25

[0363] Q15f Q15g

[0364] H H

[0365] ^>— H \ / ^>— H

[0366] 30

[0367] Q16b Q16c

[0368] H H

[0369] H

[0370] / — H 35

[0371]

[0372] Foreignfiling_text P24-256.docx

[0373] - 30 -

[0374] 5

[0375] 10

[0376] 15

[0377]

[0378] When the compounds of formula (I) or the preferred embodiments are used as matrix material for a phosphorescent emitter or in a layer directly adjacent to a phosphorescent layer, it is further preferred that the compound does not contain fused aryl or heteroaryl groups in which more than two six-membered rings are directly fused to one another. Phenanthrene and triphenylene are an exception to this, as they may be preferred despite the presence of fused aromatic six-membered rings due to their high triplet energy.

[0379] Preferably in one embodiment it may be provided that the 30 compound does not comprise an aromatic or heteroaromatic ring system which has three aromatic 6 rings condensed together.

[0380] In a preferred embodiment, the 35 compounds according to the invention have a high degree of deuteration. Preferably, the degree of deuteration can be at least 50%, preferably Foreignfiling_text P24-256.docx

[0381] - 31 -

[0382] at least 80%, particularly preferably at least 90%, and most preferably at least 95%. The degree of deuteration is determined by the numerical ratio of deuterium to the sum of deuterium and 1 H-hydrogen (D / (D+H)*100). Compounds 5 are particularly preferred fully deuterated.

[0383] The ordinary refractive indices of the compounds according to the invention, measured via ellipsometry at 450 nm, are preferably < 1.7, preferably < 1.6, particularly preferably < 1.55 and especially preferably < 1.45.

[0384] 10

[0385] Preferably, the compound according to the invention may have a molecular weight ≤ 5000 g / mol, preferably ≤ 4000 g / mol, particularly preferably ≤ 3000 g / mol, especially preferably ≤ 2000 g / mol, more preferably ≤ 1500 g / mol and most preferably ≤ 1000 g / mol.

[0386] Furthermore, preferred compounds according to the invention are characterized by being sublimable. These compounds generally have a molar mass of less than approximately 1500 g / mol.

[0387] 20

[0388] Furthermore, it may be provided that the compound according to formula (I) or a preferred embodiment of these compounds is not in direct contact with a metal atom, preferably does not represent a ligand for a metal complex.

[0389] 25

[0390] The preferred embodiments mentioned above can be combined with one another as desired within the limitations defined in claim 1. In a particularly preferred embodiment of the invention, the preferences mentioned above occur simultaneously. 30

[0391] Examples of preferred connections according to the embodiments listed above are the connections listed in the following table.

[0392] 35 Foreign filing text P24-256.docx - 122 - 5 10 15 20 25 30

[0393]

[0394] - 2S - xoop ggz-tZd ßuiiijußiajoj Foreignfiling text P24-256.docx - 122 - 5 10 15 20 25 30

[0395]

[0396] -ee- xoop ggz-tZd ßuiiijußiajoj 9£

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403]

[0404] xoop ggz-tZd )xa) BuinjuBiajod Foreignfiling text P24-256.docx - 126 - 5 10 15 20 25 30

[0405]

[0406] - 9S - xoop ggz-t Zd ßuiiijußiajoj Foreignfiling text P24-256.docx - 126 - 5 10 15 20 25 30

[0407]

[0408] - 9S - xoop ggz-t Zd ßuiiijußiajoj Foreignfiling text P24-256.docx - 122 - 5 10 15 20 25 30

[0409]

[0410] xoop ggz-tZd ßuiiijußiajoj Foreignfiling_text P24-256.docx

[0411] - 38 -

[0412] 5

[0413] 10

[0414] 15

[0415] 20

[0416] 25

[0417]

[0418] 30

[0419] The compounds 4 according to the invention can be prepared from aryl halides 1 known from the literature and the halosilanes 3 by salt metathetic reaction. For this purpose, the aryl halides 1 are first reacted with a reactive metal, such as Li, Mg 35 or Zn, or a metal-organic compound, such as an organo-lithium compound, preferably n-butyllithium, n-hexyllithium, tert-butyllithium.

[0420] - 39 -

[0421] Lithium, or a Grignard reagent, preferably isopropyl-MgCl*LiCl (Knöchel Turbo-Grignard), is transmetallated to give compounds 2. The intermediately obtained aryl-metal compounds 2 are then reacted with a mono-, di-, tri-, or tetra-halogenated silane or germane 3 to give reaction 5. Preferred reaction media are dipolar aprotic solvents such as ethers or cyclic ethers, in particular diethyl, di-n-butyl, tert-butyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, or dioxane, or mixtures thereof. The exothermic salt metathesis is preferably carried out first at cryogenic temperatures or under refrigeration; however, if necessary, the reaction can also be carried out at elevated temperatures to complete the reaction. The processing and purification of the compounds 4 according to the invention is carried out according to steps known to those skilled in the art, such as quenching, extraction, chromatography, recrystallization, fractional distillation and / or sublimation in high vacuum.

[0422] 15

[0423] Scheme 1:

[0424] 20

[0425]

[0426] 25

[0427] The siloxanes according to the invention can be prepared by hydrolysis and condensation of suitable halosilanes according to Scheme 2. The reaction sequence is carried out as described above, wherein the stoichiometry of the reaction of 2 with 3 is chosen such that the monohalosilanes 5 are formed. These are then prepared according to JP11322935 30

[0428] reacted with an oxobase, an oxide, hydroxide or carbonate to form the siloxanes 6.

[0429] 35 Foreignfiling_text P24-256.docx

[0430] -40 -

[0431] Scheme 2:

[0432] Alkyl-M* X 4-n MR M n or M* 3

[0433] - » 5 M = Si, Ge xn= 0,1,2 X: Cl, Br, IM: Li, MgX R M = R 1 , R 2 1

[0434] 5

[0435] 10

[0436]

[0437] 15

[0438] The meaning of the symbols used in the scheme set out above corresponds essentially to that defined for formula (I), although for the sake of clarity, numbering has been omitted and a full representation of all symbols has been omitted.

[0439] Another object of the present invention is therefore a method for producing a compound according to the invention, wherein first an aryl halide is converted to an aryl metal compound 25 and the aryl metal compound is then reacted with a halogen-silicon compound or a halogen-germanium compound by salt metathesis.

[0440] By these processes, optionally followed by purification, such as recrystallization or sublimation, the compounds according to the invention can be obtained in high purity, preferably more than 99% (determined by means of 1 H-NMR, HPLC and / or GC).

[0441] The compounds according to the invention can also be mixed with a polymer 35. It is also possible to covalently incorporate these compounds into a polymer. This is particularly possible with compounds, Foreignfiling_text P24-256.docx

[0442] -41 -

[0443] which are substituted with reactive leaving groups, such as bromine, iodine, chlorine, boronic acid or boronic acid esters, or with reactive, polymerizable groups, such as olefins or oxetanes. These can be used as monomers to generate corresponding oligomers, dendrimers or polymers.

[0444] 5. The oligomerization or polymerization preferably takes place via the halogen functionality or the boronic acid functionality or via the polymerizable group. It is also possible to crosslink the polymers via such groups. The compounds and polymers according to the invention can be used as a crosslinked or uncrosslinked layer 10.

[0445] Of particular interest are compounds according to the invention which are characterized by a high glass transition temperature. In this context, compounds according to formula 15 (I) or according to the preferred embodiments described above and below are particularly preferred, which have a glass transition temperature of at least 70 °C, particularly preferably at least 110 °C, very preferably at least 125 °C and most preferably at least 150 °C, as determined according to DIN 51005 (version 20 2005-08).

[0446] For processing the compounds according to the invention from the liquid phase, for example by spin coating or by pressure processes, formulations of the compounds according to the invention are required. These formulations can be, for example, solutions, dispersions, or emulsions. It may be preferred to use mixtures of two or more solvents for this purpose. Suitable and preferred solvents are, for example, toluene, anisole, o-, m-, or p-xylene, methyl benzoate, mesitylene, tetralin, veratrol, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, and (-)-fenchone.

[0447] 1,2,3,5-Tetramethylbenzol, 1,2,4,5-Tetramethylbenzol, 1 -Methylnaphthalin, 2-Methylbenzothiazol, 2-Phenoxyethanol, 2-Pyrrolidinon, 3-Methylanisol, 4- Methylanisol, 3,4-Dimethylanisol, 3,5-Dimethylanisol, Acetophenon, a- Terpineol, Benzothiazol, Butylbenzoat, Cumol, Cyclohexanol, Cyclo35 hexanon, Cyclohexylbenzol, Decalin, Dodecylbenzol, Ethylbenzoat, Indan, NMP, p-Cymol, Phenetol, 1,4-Diisopropylbenzol, Dibenzylether, Diethylen- Foreignfiling_text P24-256.docx

[0448] - 42 -

[0449] 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, 5 1,1-bis(3,4-dimethylphenyl)ethane, 2-methylbiphenyl, 3-methylbiphenyl, 1-methylnaphthalene, 1-ethylnaphthalene, ethyl octanoate, sebacic acid diethyl ester, octyl octanoate, heptylbenzene, menthyl isovalerate, cyclohexylhexanoate or mixtures of these solvents.

[0450] 10 Another object of the present invention is therefore a formulation or a composition containing at least one compound according to formula (I),

[0451] 15

[0452]

[0453] R 2 Formula (I)

[0454] wherein the symbols have the aforementioned meanings, and 20 at least one further compound. Formulations or compositions containing oligomers, dendrimers or polymers of the present invention are included herein. The further compound may, for example, be a solvent, in particular one of the solvents mentioned above or a mixture of these solvents. If the further compound 25 comprises a solvent, this mixture is referred to herein as a formulation.The further compound can also be at least one further organic or inorganic compound that is also used in the electronic device, for example, an electron transport material, a hole conductor material, an emitting compound 30 and / or a matrix material, wherein a mixture of a compound according to formula (I) and an organic or inorganic compound that is also used in the electronic device is referred to herein as the composition.

[0455] 35 Foreignfiling_text P24-256.docx

[0456] -43 -

[0457] Another object of the present invention is therefore a composition containing at least one compound according to formula (I),

[0458] 5

[0459]

[0460] R 2 Formula (I)

[0461] wherein the symbols have the aforementioned meanings and 10 at least one further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF, host materials, electron transport materials, electron injection materials, hole transport materials, hole injection materials, electron blocking materials and hole blocking materials, preferably electron injection materials, electron transport materials, hole injection materials or hole transport materials, particularly preferably electron transport materials or hole transport materials.

[0462] 20 The compounds according to the invention can be used in particular to vary the refractive index of functional layers in an electronic device, preferably an electroluminescence device, as described in more detail below. This makes it very easy to adapt and match the refractive indices of different functional layers, thereby enabling an unexpected increase in the efficiency of these devices.

[0463] The compound according to the invention can be used in combination with fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF, and / or host materials to modify their refractive index. Since the emission layer often already comprises at least two, three, or more components, and finding a power maximum is therefore complex, surprising advantages can arise from combining the compounds according to the invention in Foreignfiling_text P24-256.docx

[0464] - 44 -

[0465] an electron transport layer and / or a hole transport layer is used.

[0466] It should be noted that the compounds described above and below, which in combination with the compounds according to formula (I) and preferred embodiments of these compounds, such as hole transport materials and / or electron transport materials, often contain nitrogen atoms. Therefore, the previously stated definitions of heteroaryl groups and / or heteroaromatic ring systems must be extended to include 10 compounds containing nitrogen, boron, or phosphorus atoms. This is often indicated here by clarifying that the heteroaromatic ring systems may contain nitrogen atoms.

[0467] 15 Preferably, the proportion of compounds according to formula (I) or preferred embodiments of this formula in a composition may be in the range of 5 vol.% to 90 vol.%, particularly preferably in the range of 10 vol.% to 80 vol.% and especially preferably in the range of 30 vol.% to 70 vol.%.

[0468] 20

[0469] It is therefore preferably possible that the composition comprises at least one compound according to formula (I) or preferred embodiments of this formula and at least one hole transport material.

[0470] 25

[0471] Compounds with hole transport properties, also referred to herein as hole conductor materials or hole transport materials, are capable of transporting holes, i.e., positive charges, which are generally injected from the anode or an adjacent layer, for example, a hole injection layer. A hole transport material generally exhibits a high HOMO level, preferably at least -5.4 eV, as defined by quantum mechanical calculations. Depending on the design of an electronic device, a hole transport material can also be used as a hole injection material.

[0472] 35 Foreignfiling_text P24-256.docx

[0473] - 45 -

[0474] Preferred compounds exhibiting hole injection and / or hole transport properties include, for example, triarylamine, benzidine, tetraaryl-para-phenylenediamine, triarylphosphine, phenothiazine, phenoxazine, dihydrophenazine, thianthrene, dibenzo-para-dioxin,

[0475] 5 Phenoxathiine, carbazole, azulene, thiophene, pyrrole and furan derivatives and other 0-, S- or N-containing heterocycles with a high HOMO (HOMO = highest occupied molecular orbital).

[0476] Compounds exhibiting hole injection and / or hole transport properties 10 are preferably selected from triarylamines, in particular mono-triarylamines and bis-triarylamines, and carbazolamines. A mono-triarylamine is understood to be a compound containing a single amine group, wherein three groups selected from aromatic and heteroaromatic ring systems 15 are bonded to the nitrogen atom of the amine group. A bis-triarylamine is understood to be a compound comprising two and no further amine groups, wherein three groups selected from aromatic and heteroaromatic ring systems are bonded to each of the nitrogen atoms of the two amine groups. A carbazolamine is understood to be a compound containing 20 a carbazole group and an amine group, wherein the amine group is preferably a triarylamine group.A triarylamine group is an amine group in which three groups, selected from aromatic and heteroaromatic ring systems, are bonded to the nitrogen atom of the amine group.

[0477] 25

[0478] In a preferred embodiment, the composition may comprise at least one hole conductor material selected from compounds of formulas (L-1) and / or (L-2).

[0479] 30

[0480] Ar 15 Ar 15 Ar 15 N— Ar 15 'N— Ar 16- N

[0481] Ar 15 'Ar 15 Ar 15 35

[0482]

[0483] _ (L-1) _ _ (k2) _ Foreignfiling_text P24-256.docx

[0484] -46 -

[0485] where the following applies to the symbols:

[0486] Ar 15is selected in each occurrence, whether the same or different, from aromatic ring systems with 6 to 50 aromatic ring atoms, which are separated by R groups. 15 which can be substituted with non-H atoms, and heteroaromatic ring systems which can contain N atoms, with 5 to 40 aromatic ring atoms separated by R groups 15 can be substituted with something other than H;

[0487] 10 ares 16 In each occurrence, whether the same or different, it is selected from aromatic ring systems with 6 to 50 aromatic ring atoms, separated by R groups. 15 can be substituted with non-H atoms, and heteroaromatic ring systems that can contain N atoms, with 5 to 40 aromatic ring atoms separated by residues 15 R 15 can be substituted with something other than H;

[0488] R 15 is chosen from H, D, F, C(=O)R for each occurrence, whether the same or different. 16 , CN, Si(R 16 )3, N(R 16 )2, P(=O)(R 16 )2, OR 16 , S(=O)R16 , S(=O)2R 16 , straight-chain alkyl or alkoxy groups with 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups with 3 to 20 carbon atoms, alkenyl or alkynyl groups with 2 to 20 carbon atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems, which may contain nitrogen atoms, with 5 to 40 aromatic ring atoms; wherein 25 the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic and heteroaromatic ring systems are encoded by R groups 16 can be substituted with non-H and where one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups can each be replaced by -R 16 C=CR 16 -,

[0489] 30 -C=C-, Si(R 16 )2, C=O, C=NR 16 , -C(=O)O-, -C(=O)NR 16 -, NR 16 ,

[0490] P(=O)(R 16), -0-, -S-, SO or SO2; wherein two or more, preferably adjacent, residues R 15 together form a ring system;

[0491] 35 R 16 is chosen from H, D, in every occurrence, whether the same or different,

[0492] F, C(=O)R 17 , CN, Si(R 17 )3, N(R 17 )2, P(=O)(R 17 )2, OR 17 , S(=O)R 17 , Foreignfiling_text P24-256.docx

[0493] - 47 -

[0494] S(=O)2R 17, straight-chain alkyl or alkoxy groups with 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups with 3 to 20 carbon atoms, alkenyl or alkynyl groups with 2 to 20 carbon atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems, which may contain nitrogen atoms, with 5 to 40 aromatic ring atoms; wherein the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic and heteroaromatic ring systems are encoded by R groups 17 can be substituted with non-H and wherein one or more of the 10 CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups can each be replaced by -R 17 C=CR 17 -,

[0495] -C=C-, Si(R 17 )2, C=O, C=NR 17 , -C(=O)O-, -C(=O)NR 17 -, NR 17 , P(=O)(R 17 ), -0-, -S-, SO or SO2; wherein two or more, preferably adjacent, residues R 16 together form a 15-ring system;

[0496] R 17 The group is selected in each occurrence, either the same or different, from H, D, F, CI, Br, I, CN, alkyl groups with 1 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems, which may contain N atoms, with 5 to 40 aromatic ring atoms; wherein the alkyl groups, the aromatic and the heteroaromatic ring systems may be substituted by residues F and CN; in this case, two or more, preferably adjacent, residues R may be 17 together form a 25-ring system.

[0497] Preferred Groups Ar 15are, identical or different at each occurrence, selected from monovalent groups derived from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene, 30 in particular 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, benzocarbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine and triazine, each of the groups with residues R 15 may be substituted.

[0498] 35 Foreignfiling_text P24-256.docx

[0499] -48 -

[0500] Preferably the groups Ar 15the same or different at each occurrence selected from monovalent groups representing combinations of 2 to 4 groups selected from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene, in particular 5,9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, benzocarbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine and triazine, each of the groups with R groups 15 may be substituted.

[0501] 10

[0502] Particularly preferred groups Ar 15are, identical or different at each occurrence, selected from monovalent groups derived from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene, in particular 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzofluorene, 15-spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, carbazole, benzofuran, benzothiophene, benzo-condensed dibenzofuranyl, benzo-condensed dibenzothiophenyl, and phenyl, which is substituted with a group selected from naphthyl, phenanthrenyl, fluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzo20thiophenyl, carbazolyl, pyridyl, pyrimidyl, and triazinyl, each of the above groups with R substituents 15 may be substituted.

[0503] Preferred Groups Ar 16are, identical or different at each occurrence, selected from divalent groups derived from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene, in particular 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, benzocarbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine and triazine, each of the groups 30 with residues R 15 may be substituted.

[0504] Preferably the groups Ar 16 same or different at each occurrence chosen from monovalent groups representing combinations of 2 to 4 groups chosen from benzene, biphenyl, terphenyl, 35 quaterphenyl, naphthalene, phenanthrene, fluorene, in particular 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzofluorene, spirobifluorene, Foreignfiling_text P24-256.docx

[0505] -49 -

[0506] Indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, benzocarbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine and triazine, each of the groups with R groups 15 may be substituted.

[0507] 5

[0508] Particularly preferred groups Ar 16 are, the same or different at each occurrence, chosen from divalent groups consisting of benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene, in particular 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzofluorene, 10-spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, carbazole, benzofuran, benzothiophene, benzo-condensed dibenzofuranyl and benzo-condensed dibenzothiophenyl, each of the above groups with R substituents 15 may be substituted.

[0509] 15 Preferably R 15Equal or different choices made from H, D, F, CN, Si(R) 16 )3-, N(R 16 )2, straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups with 3 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms and heteroaromatic ring systems which may have N atoms 20, with 5 to 40 aromatic ring atoms; wherein the aforementioned alkyl and alkoxy groups and the aforementioned aromatic and heteroaromatic ring systems are entrained by R groups 16 can be substituted with something other than H.

[0510] Preferably R 16 same or different chosen from H, D, F, CN, 25 Si(R 17 )3-, N(R 17)2, straight-chain alkyl or alkoxy groups with 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups with 3 to 20 carbon atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems, which may contain nitrogen atoms, with 5 to 40 aromatic ring atoms; wherein the aforementioned alkyl and alkoxy groups and the aforementioned aromatic and heteroaromatic ring systems are modified by R groups 17 can be substituted with something other than H.

[0511] Preferably R 17 same or different at each occurrence chosen from H, D, F, CN, alkyl groups with 1 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic Foreignfiling_text P24-256.docx

[0512] - 50 -

[0513] Ring systems that can contain N atoms, with 5 to 40 aromatic ring atoms.

[0514] Particularly preferred embodiments of the compounds of formula 5 (L-1) correspond to the following formulas

[0515] 10

[0516] 15

[0517] 20

[0518] 25

[0519] 30

[0520]

[0521] 35 Foreignfiling_text P24-256.docx

[0522] - 51 -

[0523] 5

[0524]

[0525] where the symbols Ar 15 and R 15 , which have the meanings mentioned above, especially for formula (L-1) 10, and for the other symbols:

[0526] Ar 17 is selected from aromatic ring systems with 6 to 13 aromatic ring atoms, separated by R groups 15 can be substituted with non-H, and heteroaromatic ring systems that can have N atoms 15, with 5 to 13 aromatic ring atoms separated by R groups 15 can be substituted with something other than H;

[0527] X is chosen from a pair, 0, S, NR, in each occurrence, whether the same or different. 15 and (C(R) 15 )2;

[0528] 20

[0529] Y 1 is selected from 0 or S;

[0530] n is 0 or 1, where n = 0 means that the group with index n is not present and that the groups bound to the group with index n 25 are directly connected to each other, with the proviso that n is not 0 in the case of the formula (L-1 -9).

[0531] The preferred group is Ar 17 selected from divalent groups derived from benzene, biphenyl, naphthalene, fluorene, in particular 9,9'-dimethylfluorene 30 and 9,9'-diphenylfluorene, each of the groups with R substituents 15 may be substituted.

[0532] Particularly preferred are the compounds of formulas (L-1-2) and (L-1-3), wherein compounds of the following formula (L-1-2-1) as a embodiment of formula (L-1-2) are especially preferred: Foreignfiling_text P24-256.docx

[0533] - 52 -

[0534] 5

[0535]

[0536] 10 wherein the symbols and indices have the meaning set forth above and preferably correspond to the preferred embodiments mentioned above.

[0537] Particularly preferred embodiments of the compounds of formula 15 (L-2) correspond to the following formulas (L-2-1) and / or (L-2-2)

[0538] 20

[0539] 25

[0540]

[0541] 30 where the symbols Ar 15 and R 15, which have the aforementioned meanings and preferably correspond to the preferred embodiments mentioned above, and the following applies to the other symbols:

[0542] 35

[0543] Y 2 is chosen from a bond, 0, S, NR, in every occurrence, whether the same or different. 15 and (C(R) 15 )2; Foreignfiling_text P24-256.docx

[0544] - 53 -

[0545] k is 1, 2, 3 or 4, preferably 1 or 2;

[0546] i is 1, 2 or 3, preferably 1 or 2, particularly preferably 1. 5

[0547] Preferred specific compounds that can be used as hole transport material according to the present invention are listed in the following table, wherein these compounds may also be partially or completely deuterated:

[0548] 10

[0549] 15

[0550] 20

[0551] 25

[0552] 30

[0553]

[0554] 35 Foreignfiling text P24-256.docx - 126 - 5 10 15 20 25 30

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[1195] 30 Preferably, these arylamines and heterocycles, which are generally used as hole injection and / or hole transport materials, lead to a HOMO of more than -5.8 eV (vs. vacuum level), particularly preferably of more than -5.5 eV, as defined by quantum mechanical calculations.

[1196] 35 Foreignfiling_text P24-256.docx

[1197] - 97 -

[1198] According to a preferred embodiment of the present invention, the composition (hereinafter also referred to as the mixture) contains, in addition to the components of the compound according to formula (I) and the hole transport material as previously described or preferably as described in section 5, no further components, i.e., functional materials. It is therefore a material mixture that is used as such for the production of the hole transport layer. These mixtures are also referred to as premix systems, which are used as the sole material source during the evaporation of the materials for the hole transport layer and which have a constant mixing ratio during evaporation. This allows for the simple and rapid evaporation of a layer with a uniform distribution of the components without the need for precise control of a multitude of material sources.

[1199] 15

[1200] Preferred are premix systems consisting of two materials, namely a compound according to one of formulas (I), (IIa), (IIb), (IIc) or (IId) and a compound according to one of formulas (L-1) or (L-2), particularly preferably a compound according to one of formulas (IIa1), (IIb1), (IIc1) 20 or (II-d1) and a compound according to one of formulas (L-1 -1 ), (L-1 -2), (L-1 -3), (L-1 -4), (L-1 -5), (L-1 -6), (L-1 -7), (L-1 -8), (L-1 -9), (L-2-1 ) or (L-2- 2 ).

[1201] Preferably, it can further be provided that the composition comprises at least one hole transport material and at least one compound according to formula (I) or the preferred embodiments, wherein the hole transport material and the compound according to formula (I) are sublimable and the difference in the sublimation temperature is at most 5 °C, preferably at most 2 °C, wherein the sublimation temperature is determined e.g. by means of vacuum TGA measurement.

[1202] This design provides easily and safely sublimable compositions that can be used particularly reliably in a plant for the production of high-quality electronic devices 35. Foreignfiling_text P24-256.docx

[1203] - 98 -

[1204] It is therefore preferably possible that the composition comprises at least one compound according to formula (I) or preferred embodiments of this formula and at least one electron transport material.

[1205] 5

[1206] Compounds exhibiting electron injection and / or electron transport properties, hereinafter referred to as electron transport materials, include, for example, pyridine, pyrimidine, pyridazine, pyrazine, oxadiazole, quinoline, quinoxaline, anthracene, benzanthracene, pyrene, perylene, benzimidazole, triazine, ketone, phosphine oxide and phenazine derivatives, but also triarylboranes and other 0-, S- or N-containing heterocycles with a low-lying LUMO (LUMO = lowest unoccupied molecular orbital).

[1207] 15 Particularly suitable compounds for electron-transporting and electron-injecting layers are metal chelates of 8-hydroxyquinoline (e.g., LiQ, AlQ3, GaQ3, MgQ2, ZnQ2, InQ3, ZrQ4), BAIQ, Ga-oxinoid complexes, 4-azaphenanthrene-5-ol-Be complexes (US 5529853 A, see below).

[1208] Formula ET-1), butadiene derivatives (US 4356429), heterocyclic optical brighteners (US 4539507), benzimidazole derivatives (US 2007 / 0273272 A1), such as TPBI (US 5766779, see formula ET-2), 1,3,5-triazines, e.g.

[1209] Spirobifluorene-triazine derivatives (e.g. according to DE 102008064200), pyrenes, anthracenes, tetracenes, fluorenes, spirofluorenes, dendrimers, tetracenes (e.g. rubrene derivatives), 1,10-phenanthroline derivatives (JP 2003-25 115387, JP 2004-311184, JP-2001 -267080, WO 2002 / 043449), sila-cyclopentadiene derivatives (EP 1480280, EP 1478032, EP 1469533), borane derivatives such as. B. Triarylboron derivatives with Si (US 2007 / 0087219 A1, see formula ET-3), pyridine derivatives (JP 2004-200162), phenanthrolines, especially 1,10-phenanthroline derivatives, such as BCP and Bphen, also several 30 phenanthrolines linked via biphenyl or other aromatic groups (US-2007-0252517 A1) or anthracene-linked phenanthrolines (US 2007-0122656 A1, see formulas ET-4 and ET-5).

[1210] 35 Foreignfiling_text P24-256.docx

[1211] - 99 -

[1212] 5

[1213]

[1214] Formula ET-1 10

[1215] 15

[1216]

[1217]

[1218] 20

[1219]

[1220] Formula ET-5

[1221] Heterocyclic organic compounds such as e.g. are also suitable.

[1222] 25 Thiopyran dioxides, oxazoles, triazoles, imidazoles, or oxadiazoles. Examples of the use of five-membered rings with N such as oxazoles, preferably 1,3,4-oxadiazoles, which are set forth, inter alia, in US 2007 / 0273272 A1; thiazoles, oxadiazoles, thiadiazoles, triazoles, inter alia, see US 2008 / 0102311 A1 and YA Levin, MS Skorobogatova, Khimiya

[1223] 30 Geterotsiklicheskikh Soedinenii 1967 (2), 339-341 Silacyclopentadiene derivatives.

[1224] Organic compounds such as derivatives of fluorenone, fluorenylidenemethane, perylenetetracarbonic acid, anthraquinone dimethane, diphenoquinone, 35-anthrone, and anthraquinone diethylenediamine can also be used. Foreignfiling_text P24-256.docx

[1225] - 100 -

[1226] Preferred are 2,9,10-substituted anthracenes (with 1- or 2-naphthyl and 4- or 3-biphenyl) or molecules containing two anthracene units (US 2008 / 0193796 A1, see formula ET-6). Also very advantageous is the combination of 9,10-substituted anthracene units with benzimidazole-5 derivatives (US 2006 147747 A and EP 1551206 A1, see formulas ET-7 and ET-8).

[1227] 10

[1228]

[1229] Formula ET-6

[1230] 15

[1231] 20

[1232]

[1233]

[1234] 25

[1235]

[1236] Formula ET-8

[1237] 30 In a preferred embodiment, the composition may include at least one electron transport material selected from compounds of formulas (E-1) to (E-4)

[1238] 35 Foreignfiling_text P24-256.docx

[1239] - 101 -

[1240] H '-j-Ar 18

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[1242] 5

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[1246]

[1247] _ (E-3) _ _ (E-4) _

[1248] where the symbol R 15 , which has the meaning previously mentioned especially for formula (L-1) and which applies to the further symbol:

[1249] Ar 18 is selected from aromatic ring systems with 6 to 50 aromatic ring atoms, which are separated by R groups 15which can be substituted with non-H atoms, and heteroaromatic ring systems which can contain N atoms, with 5 to 50 aromatic ring atoms separated by R groups 15 can be substituted with something other than H.

[1250] 20 Compounds according to formulas (E-1) to (E-3) are preferred.

[1251] Particularly preferred embodiments of compounds that can be used as electron transport materials correspond to the following formulas (E-1-1) and / or (E-1-2)

[1252] 25

[1253] 30

[1254]

[1255] 35 Foreignfiling_text P24-256.docx

[1256] - 102 -

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[1259] where the symbols R 15 , the previously mentioned especially for formula (L-1) 10

[1260] has meaning and preferably corresponds to the preferred embodiments mentioned above, and the following applies to the other symbols:

[1261] Ar 19 is selected from aromatic ring systems with 6 to 20 aromatic ring atoms, separated by R groups 15 not equal to H substituted 15

[1262] can be, and heteroaromatic ring systems that can contain N atoms, with 5 to 20 aromatic ring atoms separated by R groups 15 can be substituted with something other than H;

[1263] m is either 0 or 1, where m = 0 means that the group with index 20

[1264] m is not present and that the group (Ar 19 ) m Bound groups are directly connected to each other.

[1265] Preferred specific compounds that can be used as electron transport materials according to the present invention are described in Figure 25.

[1266] Following Table of Contents, there are ten Materials and easy ways to protect yourself:

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[1392] According to a preferred embodiment of the present invention, the composition (hereinafter also referred to as the mixture) contains, in addition to the components of the compound according to formula (I) 20 and the electron transport material as previously or preferably described, no further components, i.e., functional materials. It is therefore a material mixture that is used as such for the production of the electron transport layer. These mixtures are also referred to as premix systems, which are used as the sole material source during the deposition of the materials for the electron transport layer and which have a constant mixing ratio during deposition. This allows the deposition of a layer with a uniform distribution of the components to be achieved in a simple and rapid manner, without the need for precise control of a large number of material sources.

[1393] Preferred are premix systems consisting of two materials, namely a compound according to one of formulas (I), (IIa), (IIb), (IIc) or (IId) and a compound according to one of formulas (E-1), (E-2), (E-3) or (E-4), particularly preferably a compound according to one of the formulas Foreignfiling_text P24-256.docx

[1394] - 109 -

[1395] (IIa1), (IIb1), (IIc1) or (IId1) and a compound according to one of the formulas (E-1-1) or (E-1-2).

[1396] Preferably, it can further be provided that the composition comprises at least one electron transport material and at least one compound according to formula (I), wherein the electron transport material and the compound according to formula (I) are sublimable and the difference in the sublimation temperature is at most 5 °C, preferably at most 2 °C, wherein the sublimation temperature is determined e.g. by means of vacuum TGA measurement.

[1397] This design provides easily and safely sublimable compositions that can be used particularly reliably in a plant for the production of high-quality electronic devices 15.

[1398] Preferably, the compounds that can generate the electron injection and / or electron transport properties lead to a LUMO of less than -2.3 eV, preferably less than -2.5 eV (compared to 20 vacuum levels), and particularly preferably less than -2.7 eV, as defined by quantum mechanical calculations.

[1399] Furthermore, the compositions according to the invention can comprise at least one hole blocking material (HBM).

[1400] 25 A hole-blocking material is a material that, in a multilayer composite, prevents or minimizes the passage of holes (positive charges), particularly if this material is arranged as a layer adjacent to an emission layer or a hole-conducting layer. Generally, a hole-blocking material has a 30 lower HOMO level than the hole-conducting material in the adjacent layer. Hole-blocking layers are frequently placed between the light-emitting layer and the electron transport layer in OLEDs.

[1401] 35 In principle, any known hole-blocking material can be used. In addition to other hole-blocking materials that are used in other Foreignfiling_text P24-256.docx

[1402] - 110 -

[1403] As set out in the present application, suitable hole-blocking materials include metal complexes (US 2003 / 0068528), such as bis(2-methyl-8-quinolinolato)(4-phenylphenolato)-aluminum(III) (BAIQ). Fac-tris(1-phenylpyrazolato-N,C2)iridium(III) 5 (Ir(ppz)3) is also used for these purposes (US 2003 / 0175553 A1). Phenanthroline derivatives, such as BCP, or phthalimides, such as TMPP, can also be used. Further suitable hole-blocking materials are described in WO 00 / 70655 A2, WO 01 / 41512, and WO 01 / 93642 A1.

[1404] 10

[1405] Furthermore, the compositions according to the invention can comprise at least one electron blocking material (EBM). An electron blocking material is a material which, in a multilayer composite, prevents or minimizes the conduction of electrons 15, particularly if this material is arranged in the form of a layer adjacent to an emission layer or an electron-conducting layer. In general, an electron blocking material has a higher LUMO level than the electron transport material in the adjacent layer.

[1406] 20

[1407] In principle, any known electron-blocking material can be used. In addition to other electron-blocking materials described elsewhere in this application, suitable electron-blocking materials include transition metal complexes 25 such as Ir(ppz)3 (US 2003 / 0175553).

[1408] Preferably, the electron blocking material can be selected from amines, triarylamines and their derivatives.

[1409] 30 Organic functional materials, such as those described above and below, are often described by the properties of the frontier orbitals, which are explained in more detail below.

[1410] The energy levels of molecular orbitals (highest occupied molecular orbital HOMO, lowest unoccupied molecular orbital LUMO, lowest triplet state Ti, lowest excited singlet state Si) are Foreignfiling_text P24-256.docx

[1411] - 111 -

[1412] Determined via quantum mechanical calculations. The Gaussian16 (Rev. B.01) software package is used in all quantum chemical calculations. The neutral singlet ground state is optimized at the B3LYP / 6-31G(d) level. HOMO and LUMO values ​​are determined at the B3LYP / 6-31G(d) level for the ground state energy optimized with B3LYP / 6-31G(d). Subsequently, TD-DFT singlet and triplet excitations (vertical excitations) are calculated using the same method (B3LYP / 6-31G(d)) and the optimized ground state geometry. The default settings for SCF and gradient convergence are used. The HOMO and LUMO values ​​in eV derived from the quantum chemical calculations are additionally scaled by the following factors:

[1413] HOMO_corr = 0.90603 * HOMO (in eV) – 0.84836

[1414] LUMO_corr = 0.99687 * LUMO (in eV) – 0.72445

[1415] 15 These values ​​are to be regarded as HOMO or LUMO energy levels of the materials for the purposes of this application.

[1416] The lowest triplet state T1 is defined as the energy of the lowest-energy triplet state resulting from the quantum chemical calculation described. The lowest excited singlet state S1 is defined as the energy of the lowest-energy excited singlet state resulting from the quantum chemical calculation described.

[1417] 25 Another object of the present invention is the use of a compound according to formula (I),

[1418] R 4

[1419] 30 R 1 -M— R 3

[1420] R 2 Formula (I)

[1421] wherein the symbols have the aforementioned meanings, in an electronic device, in particular in an organic electroluminescence device. Oligomers, dendrimers or polymers of the present invention can be used accordingly. Foreignfiling_text P24-256.docx

[1422] - 112 -

[1423] Preferably, the compounds according to formula (I) may be used in an electronic device for varying the refractive index.

[1424] 5

[1425] A further object of the present invention is an electronic device comprising at least one connection according to formula (I),

[1426] 10 R 4

[1427] R 1 -M— R 3

[1428] R 2 Formula (I)

[1429] 15, wherein the symbols have the aforementioned meanings. Electronic devices containing oligomers, dendrimers, or polymers of the present invention are included herein. An electronic device within the meaning of the present invention is a device which contains at least one layer containing at least one organic compound. The component may also contain inorganic materials or layers which are composed entirely of inorganic materials.

[1430] Particularly preferred is an electronic device selected from the group consisting of organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.), preferably organic light-emitting diodes (OLEDs), organic light-emitting diodes based on small molecules (sOLEDs), organic light-emitting diodes based on polymers (PLEDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers), “organic plasmon emitting devices” (DM Koller et al., Nature Photonics 2008, 1-4); organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs) and organic foreignfiling_text P24-256.docx

[1431] - 113 -

[1432] electrical sensors, preferably organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.), particularly preferably organic light-emitting diodes (OLEDs), organic light-emitting diodes based on small molecules (sOLEDs), organic light-emitting diodes based on polymers (PLEDs), especially phosphorescent OLEDs.

[1433] The organic electroluminescent device contains a cathode, anode, and at least one emitting layer. In addition to these layers, it may contain 10 further layers, for example, 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. Likewise,

[1434] Interlayers, which may, for example, have an exciton-blocking function, are introduced between two emitting layers. It should be noted, however, that not every one of these layers is necessarily required. The organic electroluminescent device may contain one emitting layer, or it may contain several emitting layers. If several emission layers are present, they preferably exhibit several emission maxima between 380 nm and 750 nm, resulting in overall white emission. This means that different emitting compounds capable of fluorescence or phosphorescence are used in the emitting layers. Systems with three emitting layers, wherein the three layers exhibit blue, green, and orange or red emission, are particularly preferred.The organic electroluminescence device according to the invention can also be a tandem electroluminescence device, particularly for white.

[1435] 30 emitting OLEDs.

[1436] The compound according to formula (I) or the preferred embodiments described above can be used in different layers, depending on the exact structure. An organic electroluminescent device is preferred, containing a compound according to formula (I) or the preferred embodiments described above in a Foreignfiling_text P24-256.docx

[1437] - 114 -

[1438] Electron transport layer and / or in a hole-blocking layer. Furthermore, an organic electroluminescent device is preferred, comprising a compound according to formula (I) or the preferred embodiments described above in a hole transport layer and / or

[1439] 5 Electron blocking layer. Furthermore, the compound according to formula (I) or the preferred embodiments described above can be used in an emission layer.

[1440] Emission layers generally comprise emitters. The term emitter (10) refers to a material which, after excitation (which can be achieved by the transfer of any type of energy), allows a radiative transition to a ground state, emitting light. Generally, two classes of emitters are known: fluorescent and phosphorescent emitters. The term fluorescent emitter

[1441] 15 denotes materials or compounds in which a radiative transition from an excited singlet state to the ground state occurs. The term phosphorescent emitter preferably refers to luminescent materials or compounds comprising transition metals.

[1442] 20

[1443] Emitters are often also referred to as dopants if the dopants produce the properties described above in a system. In a system containing a matrix material and a dopant, a dopant is understood to be the component whose proportion in the mixture is smaller. Similarly, in a system containing a matrix material and a dopant, a matrix material is understood to be the component whose proportion in the mixture is larger. Accordingly, the term phosphorescent emitters can also refer to phosphorescent dopants.

[1444] Preferably, the fluorescent emitter in the composition has a peak emission wavelength between 420 and 550 nm, preferably between 420 and 470 nm.

[1445] 35 Preferred fluorescent emitting compounds for hyperphosphorescent OLEDs are selected from the class of arylamines. (See Foreignfiling_text P24-256.docx)

[1446] - 115 -

[1447] In the context of the present invention, an arylamine or an aromatic amine is understood to be a compound containing three substituted or unsubstituted aromatic or heteroaromatic ring systems directly bonded to the nitrogen. Preferably, at least one of these aromatic or heteroaromatic ring systems is a condensed ring system, particularly preferably with at least 14 aromatic ring atoms. Preferred examples are aromatic anthracene, aromatic anthracenediamine, aromatic pyrene, aromatic pyrenediamine, aromatic chrysene, or aromatic chrysenediamine. An aromatic anthracene is understood to be a compound in which a diarylamine group is directly bonded to an anthracene group, preferably at position 9.An aromatic anthracenediamine is understood to be a compound in which two diarylamine groups are directly bonded to an anthracene group 15, preferably at the 9 and 10 positions. Similarly, aromatic pyrenamines, pyrendiamines, chrysenamines and chrysendiamines are defined in which the diarylamine groups are preferably bonded to the pyrene at the 1 or 1,6 position. Other preferred emitting compounds are indenofluorenamines or fluorendiamines, for example according to WO 2006 / 108497 or WO 2006 / 122630, benzoindenofluorenamines or fluorendiamines, for example according to WO 2008 / 006449, and dibenzoindenofluorenamines or didiamines, for example according to WO 2007 / 140847, as well as the indenofluorene derivatives with fused aryl groups disclosed in WO 2010 / 012328. Pyrenarylamines disclosed in WO 2012 / 048780 and WO 2013 / 185871 are also preferred.Also preferred are the benzoindenofluorenamines disclosed in WO 2014 / 037077, the benzofluorenamines disclosed in WO 2014 / 106522, the extended benzoindenofluorenes disclosed in WO 2014 / 111269 and WO 2017 / 036574, the phenoxazines disclosed in WO 2017 / 028940 and WO 2017 / 028941 30 and the furan or thiophene-bound fluorine derivatives disclosed in WO 2016 / 150544. Furthermore, boron compounds can be classified according to WO 2020 / 208051, WO 2015 / 102118, WO 2016 / 152418, WO 2018 / 095397, WO 2019 / 004248, WO 2019 / 132040, US 2020 / 0161552 and WO 2021 / 089450, WO 2015 / 102118, 35 KR 2018046851, WO 2019 / 009052, WO 2020 / 101001, US 2020 / 0207787, Foreignfiling_text P24-256.docx.

[1448] - 116 -

[1449] WO 2020 / 138874, KR 2020081978, JP 2020-147563, US 2020 / 0335705 or KR 2022041028 may be used.

[1450] Preferably, the at least one fluorescent emitter has a full width at half maximum (FWHM) ≤ 50 nm, preferably FWHM ≤ 40 nm, more preferably FWHM ≤ 30 nm.

[1451] Preferably, the at least one fluorescent emitter has a LUMO of -2.1 eV to -2.5 eV, more preferably of -2.2 eV to -2.4 eV, as defined by quantum chemical calculations. Preferably, the at least one fluorescent emitter has a HOMO of -4.8 eV to -5.2 eV, more preferably of -4.9 eV to -5.1 eV, as defined by quantum chemical calculations.

[1452] 15 Preferably the energy of the lowest singlet state S1 of the fluorescent emitter is 2.65 eV to 2.9 eV, preferably 2.7 to 2.8 eV, more preferably 2.7 to 2.75 eV, as defined by quantum mechanical calculations.

[1453] 20 In a preferred embodiment of the invention, the fluorescent emitter is selected from structures of the following formula (F-1 ),

[1454] 25

[1455]

[1456] Formula (F-1)

[1457] 30 where R has the meanings mentioned above and the following applies to the other symbols and indices used:

[1458] Ar 30 , Ar 31 , Ar 32 is the same or different in each occurrence a substituted or unsubstituted aromatic or heteroaromatic 35 ring system with 5 to 30 aromatic ring atoms, wherein the hetero- Foreignfiling_text P24-256.docx

[1459] - 117 -

[1460] aromatic ring system may contain nitrogen, boron and / or phosphorus atoms;

[1461] Y 30 is B or N;

[1462] 5

[1463] Y 31 Y 32 , Y 33is the same or different in each occurrence and stands for 0, S, C(R°)2, C=O, C=S, C=NR°, C=C(R°)2, Si(R°)2, BR°, NR°, PR°, SO2, SeO2 or a chemical bond, with the proviso that if Y 30 for B stands, at least one of the groups Y 31 , Y 32 , Y 33 stands for NR° 10, and if Y 30 N stands for at least one of the group Y 31 , Y 32 ,

[1464] Y 33 BR° stands for;

[1465] R° is the same or different in each occurrence, H, D, F, a straight-chain alkyl group with 1 to 20, preferably with 1 to 10 C atoms, or 15 a branched or cyclic alkyl group with 3 to 20, preferably with 3 to 10 C atoms, each of which may be substituted with one or more substituents R, wherein one or more non-adjacent CH2 groups may be replaced by O or S and wherein one or more H atoms may be replaced by D or F, 20 or an aromatic or heteroaromatic ring system with 5 to 40, preferably with 5 to 30, particularly preferably with 6 to 18 aromatic ring atoms, each of which may be substituted with one or more substituents R, wherein the heteroaromatic ring system may contain nitrogen, boron and / or phosphorus atoms; 25. Two adjacent substituents R° can form an aliphatic or aromatic ring system, which may be substituted with one or more substituents R;

[1466] q is either 0 or 1.

[1467] 30

[1468] Connections are particularly preferred where the following applies:

[1469] - q = 0; Y 30 = B; and Y 31 , Y 32 = NR°; or

[1470] - q = 0; Y 30 = B; and Y 31 , Y 32 = NR°; or

[1471] 35 - q = 1; Y 30 = N; and Y 31 , Y 32 = BR°; Y 33 = chemical bond. Foreignfiling_text P24-256.docx

[1472] - 118 -

[1473] Examples of suitable fluorescent emitters are shown in the table below: _ _

[1474] DD

[1475] 5

[1476] omro O ^^ 0 D D D

[1477] 10 P, J? QQ=\ 15W, 95W

[1478] crxtro V f Ä"

[1479] X Q z- % i.qiX rX) 15 P Or

[1480] oo 9

[1481] 20 W

[1482] omm xrxirrx

[1483] 25 OL JO qm m om crm c

[1484] 30

[1485] W O UO month-Q

[1486]

[1487] 35 Foreignfiling text P24-256.docx - 122 - 5 10 15 20 25 30

[1488]

[1489] - 6k ​​k - xoop ggz-tZd ßuiiijußiajoj 9£

[1490]

[1491]

[1492]

[1493]

[1494]

[1495]

[1496]

[1497] xoop ggz-tZd )xa) BuinjuBiajod Foreignfiling_text P24-256.docx

[1498] - 121 -

[1499] 5

[1500] 10

[1501] 15

[1502] 20

[1503] 25

[1504] 30

[1505]

[1506] 35 Foreign filing text P24-256.docx - 122 - 5 10 15 20 25 30

[1507]

[1508] - 122 - Foreignfiling text P24-256.docx Foreignfiling_text P24-256.docx

[1509] - 123 -

[1510] 5

[1511]

[1512] 10

[1513] The following are examples of preferred compounds that can serve as phosphorescent emitters. The term "phosphorescent compound" or "phosphorescent compound" (= triplet emitter) typically refers to compounds in which the emission of light occurs through a spin-forbidden transition, e.g., a transition of 15

[1514] transition from an excited triplet state or a state with a higher spin quantum number, e.g., a quintet state. Luminescent complexes with transition metals or lanthanides are preferred as phosphorescent compounds, especially when they contain copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, 20

[1515] The compounds contain indium, palladium, platinum, silver, gold, or europium, particularly compounds containing indium, platinum, or copper. Within the scope of the present invention, all luminescent indium, platinum, or copper complexes are considered phosphorescent emitting compounds. Iridium or platinum complexes are particularly preferred.

[1516] 25

[1517] Examples of phosphorescent emitters can be found in applications WO 00 / 70655, WO 2001 / 41512, WO 2002 / 02714, WO 2002 / 15645, EP 1191613, EP 1191612, EP 1191614, WO 05 / 033244, WO 05 / 019373, US 2005 / 0258742, WO 2009 / 146770, WO 2010 / 015307, WO 2010 / 031485, 30

[1518] WO 2010 / 054731, WO 2010 / 054728, WO 2010 / 086089, WO 2010 / 099852, WO 2010 / 102709, WO 2011 / 032626, WO 2011 / 066898, WO 2011 / 157339, WO 2012 / 007086, WO 2014 / 008982, WO 2014 / 023377, WO 2014 / 094961, WO 2014 / 094960, WO 2015 / 036074, WO 2015 / 104045, WO 2015 / 117718, WO 2016 / 015815, WO 2016 / 124304, WO 2017 / 032439, WO 2018 / 011186, 35

[1519] WO 2018 / 041769, WO 2019 / 020538, WO 2018 / 178001, WO 2019 / 115423 and WO 2019 / 158453 can be extracted. Generally, all Foreignfiling_text P24-256.docx files are suitable.

[1520] - 124 -

[1521] Phosphorescent complexes, such as those used in phosphorescent OLEDs according to the prior art and as known to those skilled in the art in the field of organic electroluminescence, and those skilled in the art can use further phosphorescent complexes without inventive effort. Since the compounds to be used according to the invention can also have a high triplet energy depending on the substitution, it is particularly possible to use them as matrix material for blue phosphorescent emitters.

[1522] 10 Suitable phosphorescent metal complexes that can be used in phosphorescent OLEDs or as sensitizers in hyperphosphorescent OLEDs are further disclosed, inter alia, in Sungho Nam et al., Adv. Sci. 2021, 2100586, Eungdo Kin et al., Sci. Adv. 2022, 8, 1641. Further compounds suitable as sensitizers are disclosed in EP

[1523] 15 3435438 A2, in particular connections 2 and 3 on page 21, in CN 109111487, in particular connections on pages 76 and 77, in US 2020 / 0140471, in particular connections on pages 166 to 175; in KR 2020108705, in particular the compounds on pages 8 to 14, in US 2019 / 0119312, in particular the compounds on pages 114 to 121, and in US 2020 / 0411775, in particular the compounds on pages 123 to 128. Further suitable phosphorescent metal complexes are disclosed in US 2022 / 0115607, US 2022 / 0298193, US 2016 / 0072082 and US 2022 / 0271236.

[1524] 25 The proportion of matrix material in the emitting layer is in this case between 50.0 and 99.9 vol.%, preferably between 80.0 and 99.5 vol.%, particularly preferably between 92.0 and 99.5 vol.% for fluorescent emitting layers and between 85.0 and 97.0 vol.% for phosphorescent emitting layers.

[1525] 30

[1526] Accordingly, the proportion of the emitting compound is between 0.1 and 50.0 vol.%, preferably between 0.5 and 20.0 vol.%, and particularly preferably between 0.5 and 8.0 vol.% for fluorescent emitting layers and between 3.0 and 15.0 vol.% for phosphorescent emitting layers. Foreignfiling_text P24-256.docx

[1527] - 125 -

[1528] An emitting layer can also comprise systems containing a variety of matrix materials (mixed matrix systems) and / or a variety of emitting compounds. In this case, too, the emitting compounds are usually those with the smaller proportion in the system, and the matrix materials are those with the larger proportion. In some cases, however, the proportion of a single matrix material in the system may be smaller than the proportion of a single emitting compound.

[1529] 10. Preferably, mixed matrix systems can be used. The mixed matrix systems preferably consist of two or three different matrix materials, particularly preferably of two different matrix materials. Preferably, one of the two materials is a material with hole-transporting properties and the other material is a 15 material with electron-transporting properties. Further mixed matrix components can also fulfill other functions. The two different matrix materials can be present in a ratio of 1:50 to 1:1, preferably 1:20 to 1:1, even more preferably 1:10 to 1:1, and most preferably 1:4 to 1:1. Mixed matrix 20 systems are preferably used in phosphorescent or hyperphosphorescent organic electroluminescent devices.Particularly suitable matrix materials that can be used in combination with the compounds according to the invention as matrix components of a mixed matrix system are described in more detail below.

[1530] 25

[1531] Examples of phosphorescent compounds are listed below.

[1532] 30

[1533] 35

[1534]

[1535] Foreign filing text P24-256.docx - 126 - 5 10 15 20 25 30

[1536]

[1537] - 126 - Foreignfiling text P24-256.docx Foreignfiling text P24-256.docx - 122 - 5 10 15 20 25 30

[1538]

[1539] - 127 - Foreign filing text P24-256.docx

[1540]

[1541] Foreignfiling_text P24-256.docx

[1542] - 129 -

[1543] In a preferred embodiment, a suitable combination of compounds preferably forms a hyperfluorescence and / or hyperphosphorescence system. Such hyperfluorescence and / or hyperphosphorescence systems constitute a preferred embodiment of the 5 compounds according to the invention.

[1544] Preferably, a fluorescent emitter is used in combination with one or more phosphorescent materials (triplet emitters) and / or a compound that is a TADF host material.

[1545] 10 (thermally activated delayed fluorescence).

[1546] In WO 2015 / 091716 A1 and WO 2016 / 193243 A1, OLEDs are disclosed which contain both a phosphorescent compound and a fluorescent emitter in the emission layer, wherein the energy is transferred from the phosphorescent compound to the fluorescent emitter (hyperphosphorescence). In this context, the phosphorescent compound thus behaves like a host material. As is known to those skilled in the art, host materials have higher singlet and triplet energies compared to the emitters so that the energy of the host material is transferred to the emitter as efficiently as possible. The systems disclosed in the prior art exhibit precisely such an energy ratio.

[1547] A fluorescent emitter can preferably be used in combination with a 25 TADF host material and / or a TADF emitter, as previously outlined.

[1548] The process known as thermally activated delayed fluorescence (TADF) is described, for example, by BH Uoyarna et al., Nature 2012, Vol. 492, 234. To enable this process, a comparatively small singlet-triplet distance ΔE(S1–T1) of, for example, less than about 2000 cm is required in the emitter. -1 necessary. In order to open the otherwise spin-forbidden Ti-Si transition, another connection can be provided in matrix 35 next to the emitter, which exhibits strong spin-orbit coupling, so that the spatial proximity and the resulting possible interaction between Foreignfiling_text P24-256.docx

[1549] - 130 -

[1550] Inter-system crossing is enabled for the molecules, or spin-orbit coupling is generated via a metal atom contained in the emitter.

[1551] Besides emitters, emission layers often include host materials, which are also frequently referred to as matrix materials. Compounds used as host materials, especially together with emitting compounds, include materials from various classes of substances.

[1552] Host materials generally exhibit larger band gaps between the HOMO and LUMO than the emitter materials used. Additionally, preferred host materials display either hole-transport or electron-transport material properties. Furthermore, host materials can exhibit both electron- and hole-transport properties. Host materials are sometimes also referred to as matrix materials, particularly when the host material is used in combination with a phosphorescent emitter in an OLED.

[1553] Preferred host materials or co-host materials, which are used in particular together with fluorescent dopants, are selected from the classes of oligoarylenes (e.g. 2,2',7,7'-tetraphenyl-spirobi-fluorene according to EP 676461 or dinaphthylanthracene), in particular oligoarylenes containing condensed aromatic groups such as e.g.

[1554] Anthracene, benzanthracene, benzphenanthrene (DE 102009005746, WO 25 09 / 069566), phenanthrene, tetracene, coronene, chrysene, fluorene, spirofluorene, perylene, phthaloperylene, naphthaloperylene, decacyclene, rubrene, the oligoarylene vinylenes (e.g. DPVBi = 4,4'-bis(2,2-diphenyl-ethenyl)-1, T-biphenyl ) or spiro-DPVBi according to EP 676461), the polypodal metal complexes (e.g. according to WO 04 / 081017), in particular metal complexes of 30 8-hydroxyquinoline, e.g. B. AlQ3(= Aluminium(III)tris(8-hydroxyquinoline)) or Bis(2-methyl-8-quinolinolato)-4-(phenylphenolinolato)aluminium, also with imidazole chelate (US 2007 / 0092753 A1) as well as the quinoline metal complexes, aminoquinoline metal complexes, benzoquinoline metal complexes, the hole-conducting compounds (e.g. according to WO 04 / 058911), the electron-conducting compounds, in particular ketones, phosphine oxides, sulfoxides, carbazoles, spirocarbazoles, indenocarbazoles, etc. (e.g. according to Foreignfiling_text P24-256.docx

[1555] - 131 -

[1556] WO 05 / 084081 and WO 05 / 084082), the atropisomers (e.g. according to WO 06 / 048268), the boronic acid derivatives (e.g. according to WO 06 / 117052) or the benzanthracenes (e.g. according to WO 08 / 145239).

[1557] 5 Particularly preferred compounds that can serve as host materials or co-host materials are selected from the classes of oligoarylenes containing anthracene, benzanthracene and / or pyrene or atropisomers of these compounds. For the purposes of the present invention, an oligoarylene is understood to be a compound in which at least three aryl or arylene groups are bonded together.

[1558] Preferred host materials are in particular selected from compounds of formula (H-100),

[1559] 15 ares 5 -(Ar 6 ) P -Ar 7 (H-100)

[1560] where Ar 5 , Ar 6 , Ar 7where, in each occurrence, the aryl or heteroaryl group with 5 to 30 aromatic ring atoms is the same or different, and may optionally be substituted, and p represents an integer in the range 20 from 1 to 5; where the sum of the TT electrons in Ar 5 , Ar 6 and Ar 7 at least 30 if p = 1, and at least 36 if p = 2, and at least 42 if p = 3.

[1561] The 25 group Ar is particularly favored in the compounds of formula (H-100). 6 for Anthracenes and the Ar groups 5 and Ar 7 are bound in positions 9 and 10, whereby these groups may be substituted. At least one of the groups Ar is particularly preferred. 5 and / or Ar 7a fused aryl group selected from 1- or 2-naphthyl, 2-, 3- or 9-phenanthrenyl, or 2-, 3-, 4-, 5-, 6- or 7-benz-30 anthracenyl. Anthracene-based compounds are described in US 2007 / 0092753 A1 and US 2007 / 0252517 A1, e.g. B. 2-(4-Methylphenyl)-9,10-di-(2-naphthyl)anthracene, 9-(2-naphthyl)-10-(1,1'-biphenyl)anthracene and 9,10-bis[4-(2,2-diphenylethenyl)phenyl]anthracene, 9,10-diphenyl-anthracene, 9,10-bis(phenylethynyl)anthracene and 1,4-bis(9'-ethynyl-35anthracenyl)benzene. Compounds with two Foreignfiling_text P24-256.docx

[1562] - 132 -

[1563] Anthracene units (US 2008 / 0193796 A1), e.g. 10, 10'-Bis[1, 1 ',4', 1”]terphenyl-2-yl-9,9'-bisanthracenyl.

[1564] Other preferred compounds are derivatives of arylamine, styrylamine, 5-fluorescein, diphenylbutadiene, tetraphenylbutadiene, cyclopentadiene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, coumarin, oxadiazole, bisbenzoxazoline, oxazole, pyridine, pyrazine, imine, benzothiazole, benzoxazole, benzimidazole (US 2007 / 0092753 A1), e.g. B. 2,2',2”-(1,3,5-phenylene)tris[1-phenyl-1H-benzimidazole], Aldazine, Stilbene, Styrylarylene- 10 derivatives, e.g. 9,10-Bis[4-(2,2-diphenylethenyl)phenyl]anthracene and Distyrylarylene derivatives (US 5121029), Diphenylethylene, Vinylanthracene, Diaminocarbazole, Pyran, Thiopyran, Diketopyrrolopyrrole, Polymethine, Cinnamic acid esters and Fluorescent dyes.

[1565] 15 Particularly preferred are derivatives of arylamine and styrylamine, e.g. TNB (= 4,4'-bis[N-(1-naphthyl)-N-(2-naphthyl)amino]biphenyl). Metal-oxinoid complexes such as LiQ or AlQ3 can be used as co-hosts.

[1566] Preferred compounds with oligoaryls as a matrix are in the US

[1567] 20 2003 / 0027016 A1, US 7326371 B2, US 2006 / 043858 A, WO 2007 / 114358, WO 08 / 145239, JP 3148176 B2, EP 1009044, US 2004 / 018383, WO 2005 / 061656 A1, EP 0681019B1, WO 2004 / 013073A1, US 5077142, WO 2007 / 065678 and DE 102009005746, wherein particularly preferred compounds are described by formulas H-102 to H-108.

[1568] 25

[1569] 30

[1570]

[1571] Formula H-102 Formula H-103

[1572] 35 Foreignfiling_text P24-256.docx

[1573] - 133 -

[1574] 5

[1575]

[1576] Formula H-104 10

[1577] 15

[1578]

[1579] 20

[1580]

[1581]

[1582] Furthermore, compounds that can be used as a host or matrix include materials that are used together with phosphorescent emitters. Preferred matrix materials for phosphorescent compounds, which can also be used in combination with the compounds according to the invention, are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g. according to WO 2004 / 013080, WO 2004 / 093207, WO 2006 / 005627 or WO 2010 / 006680, triarylamines, carbazole derivatives, etc. B. CBP (N,N-Biscarbazolylbiphenyl) or WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 288381, EP 1205527, WO 2008 / 086851 or WO 2013 / 041176, indolocarbazole derivatives, e.g. according to WO 2007 / 063754 or WO 2008 / 056746, indenocarbazole derivatives, e.g. according to WO 2010 / 136109, WO 2011 / 000455, WO 2013 / 041176 or WO 2013 / 056776, azacarbazole- Foreignfiling_text P24-256.docx

[1583] - 134 -

[1584] derivatives, e.g. according to EP 1617710, EP 1617711, EP 1731584, JP 2005 / 347160, bipolar matrix materials, e.g. according to WO 2007 / 137725, silanes, e.g. according to WO 2005 / 111172, azaborols or boron esters, e.g. according to WO 2006 / 117052, triazine derivatives, e.g. according to WO 2007 / 063754, WO 2008 / 056746, WO 2010 / 015306, WO 2011 / 057706, WO 2011 / 060859 or WO 2011 / 060877, zinc complexes, e.g. B. according to EP 652273 or WO 2009 / 062578, diazasilol or tetraazasilol derivatives, e.g. according to WO 2010 / 054729, diazaphosphole derivatives, e.g. according to WO 2010 / 054730, bridged carbazole derivatives, e.g. according to WO 2011 / 042107, WO

[1585] 10 2011 / 060867, WO 2011 / 088877 and WO 2012 / 143080, triphenylene derivatives, e.g. according to WO 2012 / 048781, lactams, e.g. according to WO 2011 / 116865 or WO 2011 / 137951, dibenzofuran derivatives, e.g. according to WO 2015 / 169412, WO 2016 / 015810, WO 2016 / 023608, WO 2017 / 148564 or WO 2017 / 148565 or bridged triarylboron compounds, for example15 according to US 2021 / 0122765. Similarly, another phosphorescent emitter, which emits at a shorter wavelength than the actual emitter, may be present in the mixture as a co-host, or a compound that does not participate in charge transport or does not participate to a significant extent, as described, for example, in WO 2010 / 108579.

[1586] 20

[1587] The previously cited publications describing the functional materials that can be used to produce functional layers of electronic devices are incorporated into the present application for disclosure purposes by reference. 25

[1588] Furthermore, it may be provided that the electronic device is an organic electroluminescent device and the electroluminescent device comprises an electron transport layer, wherein the electron transport layer comprises at least one electron transport material and 30 a compound according to formula (I).

[1589] Preferably, the electron transport layer can contain a composition according to the invention, preferably consisting of a composition according to the invention, wherein this composition is a

[1590] 35 electron transport materials are included. Foreignfiling_text P24-256.docx

[1591] - 135 -

[1592] Furthermore, it may be provided that the electronic device is an organic electroluminescent device and that the electroluminescent device comprises a hole transport layer, wherein the hole transport layer comprises at least a hole conductor material and a compound according to formula (I) 5.

[1593] Preferably the hole transport layer can contain a composition according to the invention, preferably consisting of a composition according to the invention, wherein this composition comprises a hole10 conductor material.

[1594] The ordinary refractive indices of the layers of an electronic device, preferably an organic electroluminescence device, measured via ellipsometry at 450 nm, are preferably less than 1.8, more preferably less than 1.7, more preferably less than 1.6 and particularly preferably less than 1.5.

[1595] In the further layers of the organic electroluminescent device according to the invention, all materials commonly used in the prior art can be employed. Therefore, without any inventive effort, a person skilled in the art can use all materials known for organic electroluminescent devices in combination with the compounds according to formula (I) or the preferred embodiments described above.

[1596] 25

[1597] In addition to the layers described above, an electronic device, preferably an organic electroluminescent device, may comprise further layers. In particular, a compound according to formula (I) or preferred embodiments of this formula may be used to

[1598] 30 Production of an outcoupling layer, a capping layer or a matching layer. A further preferred subject matter of the present invention is therefore an electronic device, preferably an organic electroluminescent device, with a 35 outcoupling layer, a capping layer or

[1599] Capping layer or an adaptation layer that connects to Foreignfiling_text P24-256.docx

[1600] - 136 -

[1601] ing according to formula (I) or preferred embodiments of this formula comprises, preferably consisting of one or more of these compounds.

[1602] Preferred electroluminescent devices (OLEDs) 5 according to the invention comprise the following layer structure, whereby it is not excluded that further layers are present:

[1603] - Anode

[1604] - Bone Injectable Layer (HIL)

[1605] - Hole transport layer (HTL)

[1606] 10 - Electron Blocking Layer (EBL)

[1607] - Emission layer (EML) containing a fluorescent or phosphor dopant

[1608] - Hole-blocking layer (HBL)

[1609] - Electron transport layer (ETL)

[1610] 15 - Electron injection layer

[1611] - Cathode.

[1612] Various embodiments of the invention are summarized in the following table:

[1613] 20

[1614] EML compound of formula (I) or preferred embodiments in the following layer

[1615] 1 fluorescent HIL

[1616] 25 2 fluorescent HTL

[1617] 3 fluorescent EBL

[1618] 4 fluorescent HBL

[1619] 5 fluorescent ETL

[1620] 6 fluoreszent HIL + HTL

[1621] 30

[1622] 7 fluoreszent HIL + EBL

[1623] 8 fluoreszent HIL + HBL

[1624] 9 fluoreszent HIL + ETL

[1625] 10 fluoreszent HTL + EBL

[1626] 11 fluoreszent HTL + HBL

[1627] 35

[1628] 12 fluoreszent HTL + ETL

[1629]

[1630] 13 fluoreszent EBL + HBL Foreignfiling_text P24-256.docx

[1631] - 137 -

[1632] 14 fluoreszent EBL + ETL

[1633] 15 fluoreszent HBL + ETL

[1634] 16 fluoreszent HIL + HTL + EBL

[1635] 17 fluoreszent HIL + HTL + HBL

[1636] 5

[1637] 18 fluoreszent HIL + HTL + ETL

[1638] 19 fluoreszent HIL + EBL + HBL

[1639] 20 fluoreszent HIL + EBL + ETL

[1640] 21 fluoreszent HIL + HBL + ETL

[1641] 22 fluoreszent HTL + EBL + HBL

[1642] 10

[1643] 23 fluoreszent HTL + EBL + ETL

[1644] 24 fluoreszent HTL + HBL + ETL

[1645] 25 fluoreszent EBL + HBL + ETL

[1646] 26 fluoreszent HIL + HTL + EBL + HBL 27 fluoreszent HIL + HTL + HBL + ETL 15

[1647] 28 fluoreszent HTL + EBL + HBL + ETL 29 fluoreszent HIL + HTL + EBL + HBL + ETL 30 phosphoreszent HIL

[1648] 31 phosphoreszent HTL

[1649] 20 32 phosphoreszent EBL

[1650] 33 phosphoreszent HBL

[1651] 34 phosphoreszent ETL

[1652] 35 phosphoreszent HIL + HTL

[1653] 36 phosphoreszent HIL + EBL

[1654] 25 37 phosphoreszent HIL + HBL

[1655] 38 phosphoreszent HIL + ETL

[1656] 39 phosphoreszent HTL + EBL

[1657] 40 phosphoreszent HTL + HBL

[1658] 41 phosphoreszent HTL + ETL

[1659] 30 42 phosphoreszent EBL + HBL

[1660] 43 phosphoreszent EBL + ETL

[1661] 44 phosphoreszent HBL + ETL

[1662] 41 phosphoreszent HIL + HTL + EBL

[1663] 42 phosphoreszent HIL + HTL + HBL

[1664] 35 43 phosphoreszent HIL + HTL + ETL

[1665]

[1666] 44 phosphoreszent HIL + EBL + HBL Foreignfiling_text P24-256.docx

[1667] - 138 -

[1668] 45 phosphoreszent HIL + EBL + ETL

[1669] 46 phosphoreszent HIL + HBL + ETL

[1670] 47 phosphoreszent HTL + EBL + HBL

[1671] 48 phosphoreszent HTL + EBL + ETL

[1672] 5

[1673] 49 phosphoreszent HTL + HBL + ETL

[1674] 50 phosphoreszent EBL + HBL + ETL

[1675] 51 phosphorescent HIL + HTL + EBL + HBL

[1676] 52 phosphorescent HIL + HTL + HBL + ETL

[1677] 53 phosphorescent HTL + EBL + HBL + ETL

[1678] 10

[1679]

[1680] 54 phosphorescent HIL + HTL + EBL + HBL + ETL

[1681] The fluorescent or phosphorescent EML can emit blue, green, yellow, or red light, respectively. In a preferred embodiment, the fluorescent EML is a blue-emitting layer. The fluorescent EML can emit blue light in various ways.

[1682] The EML can also be a hyperfluorescent EML containing a TADF compound as a sensitizer, or a hyperphosphorescent EML containing a phosphorescent compound as a sensitizer. In a further preferred embodiment, the phosphorescent EML is a green, yellow, or red emitting layer.

[1683] 20

[1684] A further preferred organic electroluminescence device is characterized in that one or more layers are coated using a sublimation process. The materials are applied in vacuum sublimation systems at an initial pressure of less than 10⁻⁵ m. 5 mbar, 25

[1685] preferably smaller than 10' 6 mbar vapor deposition. However, it is also possible that the initial pressure is even lower, for example less than 10⁻⁶ mbar. 7 mbar.

[1686] An organic electroluminescence device is also preferred, characterized in that one or more layers with the 30

[1687] The materials can be coated using OVPD (Organic Vapor Phase Deposition) or with the aid of carrier gas sublimation. In this process, the materials are coated at a pressure between 10°C and 10°C. 5mbar and 1 bar are applied. A special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and thus

[1688] 35

[1689] be structured. Foreignfiling_text P24-256.docx

[1690] - 139 -

[1691] A further preferred organic electroluminescent device is characterized in that one or more layers are produced from solution, e.g., by spin coating, or by any printing process, e.g., screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), inkjet printing, or nozzle printing. Soluble compounds are required for this purpose, which can be obtained, for example, by suitable substitution.

[1692] Formulations for applying a compound according to formula (I) or 10 of its previously described preferred embodiments are novel. A further object of the present invention is therefore a formulation comprising at least one solvent and a compound according to formula (I) or the previously described preferred embodiments.

[1693] 15

[1694] Hybrid processes are also possible, in which, for example, one or more layers of solution are applied and one or more further layers are vapor-deposited.

[1695] 20 These methods are generally known to the person skilled in the art and can be applied by him without inventive effort to organic electroluminescent devices containing the compounds according to formula (I) or the preferred embodiments described above and below.

[1696] 25 The compounds and organic electroluminescent devices according to the invention can, depending on the specific embodiment, be characterized by a low refractive index (RI). Furthermore, these compounds and the organic electroluminescent devices obtained therefrom exhibit an improved lifetime. The other electronic properties of the electroluminescent devices, such as efficiency, remain at least as good. In a further embodiment, the compounds and organic electroluminescent devices according to the invention are characterized, compared to the prior art, in particular by improved efficiency and / or a longer lifetime. Foreignfiling_text P24-256.docx

[1697] - 140 -

[1698] The electronic devices according to the invention, in particular organic electroluminescence devices, are characterized by one or more of the following surprising advantages over the prior art:

[1699] 5

[1700] 1. Electronic devices, in particular organic electroluminescent devices containing compounds according to formula (I) or the preferred embodiments described above and below, especially in combination with an emitter, 10 with a matrix material, with a hole-conducting material or with an electron-conducting material, exhibit excellent efficiency.

[1701] 2. Electronic devices, in particular organic electroluminescent devices containing compounds according to formula (I) or the preferred embodiments described above and below, especially in combination with an emitter, with a matrix material, with a hole-conducting material or with an electron-conducting material, have a very good lifetime.

[1702] 3. The compounds according to formula (I) or the preferred embodiments described above and below exhibit very high stability.

[1703] 25

[1704] 4. The compounds according to formula (I) or the preferred embodiments described above and below have very low refractive indices and, when used in electronic devices, in particular organic electroluminescent devices, lead to layers having very low refractive indices.

[1705] 5. Compounds according to formula (I) or the preferred embodiments described above and below can be used in electronic devices, in particular organic electroluminescence pre- Foreignfiling_text P24-256.docx

[1706] - 141 -

[1707] directions that avoid the formation of losses due to optical reflection.

[1708] 6. Compounds according to formula (I) or the preferred embodiments described above and below from 5 exhibit excellent glass film formation.

[1709] 7. Compounds according to formula (I) or the preferred embodiments described above and below form very good films from solutions 10.

[1710] These aforementioned advantages do not come at the cost of an excessively high deterioration of other electronic properties.

[1711] 15 It should be noted that variations of the embodiments described in the present invention fall within the scope of this invention. Unless explicitly excluded, each feature disclosed in the present invention may be replaced by alternative features serving the same, an equivalent, or a similar purpose. Thus, unless otherwise stated, each feature disclosed in the present invention is to be considered as an example of a generic series or as an equivalent or similar feature.

[1712] 25 All features of the present invention can be combined with one another in any way, unless certain features and / or steps are mutually exclusive. This applies in particular to preferred features of the present invention. Likewise, features of non-essential combinations can be used separately 30 (and not in combination).

[1713] It should further be noted that many of the features, and in particular those of the preferred embodiments of the present invention, are themselves inventive and not merely to be considered part of embodiment 35 of the present invention. For these features, Foreignfiling_text P24-256.docx

[1714] - 142 -

[1715] Independent protection may be sought in addition to or as an alternative to any invention currently claimed.

[1716] The teaching disclosed by the present invention for technical purposes

[1717] 5. Action can be abstracted and combined with other examples.

[1718] The invention is further explained by the following examples, without thereby limiting its scope. A person skilled in the art can implement the invention in its entire disclosed area from the descriptions.

[1719] 10 and without inventive effort produce further compounds according to the invention and use them in electronic devices or apply the method according to the invention.

[1720] Examples:

[1721] 15. Unless otherwise stated, the following syntheses are carried out under a protective gas atmosphere in dried solvents. The solvents and reagents can be obtained, for example, from Sigma-Aldrich or ABCR. The respective information in square brackets or the numbers given for individual compounds are

[1722] 20 refers to the CAS numbers of the compounds known from the literature.

[1723] For compounds that can have several isomeric, enantiomeric, diastereomeric or tautomeric forms, one form is shown as a representative example.

[1724] 25 A: Synthons known from literature:

[1725] 30

[1726]

[1727] 35 Foreignfiling_text P24-256.docx

[1728] - 143 -

[1729] 5

[1730] 10

[1731] 15

[1732] 20

[1733] 25

[1734] 30

[1735] 35

[1736]

[1737] 2) ArylBromide AB: Foreignfiling_text P24-256.docx

[1738] - 144 -

[1739] 169695-24-3 554402-79-8

[1740] 5 1562418-82-9

[1741] AB1 AB2 AB3

[1742] D

[1743] Br / | / x

[1744] D Br ^ £^JOA< FF 10 1562418-80-7

[1745] 1562418-83-0 1562418-85-2 AB4

[1746] AB5 AB6 F

[1747] D3 V CD3

[1748] 15

[1749] Br ' xx ^ x / \ C °

[1750] 3 3

[1751] D C CD 3

[1752] 1562418-84-1 1562418-81-8 1562418-94-3 AB7 AB8 AB9

[1753] 20

[1754] ^ Br / x^ x X / X\ 3006054-57-2

[1755] 3006050-34-3 3006050-35-4 25 AB10

[1756] AB11 AB12

[1757] Br Y^IxxJ

[1758] 27452-17-1 119999-22-3 2767302-10-1 30

[1759] AB30 AB31 AB32

[1760] F

[1761] J. F \ /

[1762] OUo< F X I J

[1763] F

[1764] 35 Br ^XX Br ^XX 2375921-67-6 1229822-48-3 2835450-70-7 AB33

[1765]

[1766] AB34 AB35 Foreignfiling_text P24-256.docx

[1767] - 145 -

[1768] 5 BO Br J JÖ>\

[1769] 2559731-19-8

[1770] AB36

[1771] 10

[1772] Xjß

[1773] 16499-72-2 1801624-95-2 AB50 1562418-87-4 AB52

[1774] AB51

[1775] 15

[1776] Br ^^V^

[1777] Br BK ^^y

[1778] 20

[1779] 1801624-96-3

[1780] AB53 2649510-09-6 2649510-10-9 AB54 AB55

[1781] 25

[1782] 1801624-97-4 B / BrJ3CV AB70 2413719-28-3 2413719-30-7 AB71 AB72 30

[1783] — C / ^~ Br

[1784] L\^Br 1935965-17-5 2245-43-4 1459-53-6

[1785] AB101

[1786]

[1787] AB 100 AB 102 35 Foreignfiling_text P24-256.docx

[1788] - 146 -

[1789] 3) Halogenosilanes with alkyl group substitution according to the invention: MonoHalogenSilane EMHS, DiHalogenSilane EDHS, TriHalogenSilane ETHS

[1790] 5

[1791] 3038486-44-8 1401573-71-4 10 EMHS1 EMHS2 EMHS3

[1792] 15

[1793] 1401573-63-4

[1794] EMHS4 EMHS5

[1795] EMHS100

[1796] 20

[1797] ci 70402-94-7 25 EDHS1

[1798]

[1799] ETHS2

[1800] 4) MonoHalogenSilane MHS, MonoHalogenGermane MHG:

[1801] CD3

[1802] — Si— I.

[1803] D3C Si CD3

[1804] I / I 30 Cl Cl Cl 75-77-4 20395-57-7 17680-28-3 MHS1 MHS2 MHS3 \ I / / -Si— / Si— / >— Si— ( / I / I Cl / I \ \ 35 Cl Cl 994-30-9 13154-24-0 3634-57-9

[1805]

[1806] MHS4 MHS5 MHS6 Foreignfiling_text P24-256.docx

[1807] - 147 -

[1808] 5

[1809] 10

[1810] 15

[1811] 20

[1812] 25

[1813] 30

[1814] 35

[1815]

[1816] Foreignfiling_text P24-256.docx

[1817] - 148 -

[1818] ( x > ( z x >— Si— Cl

[1819] Ch fc > 41081-31-6

[1820] 58479-61-1 5 MHS106 76814-99-8

[1821] MHS107 MHS108

[1822] if

[1823] / 7— Si— ( /

[1824] \ _ / I \ _ /

[1825] 10 o?o \Z — c

[1826] / - Cl — \;i— (

[1827] / \= / ( ,| \ / / \ 76-86-8 111795-44-9

[1828] 119707-75-4 MHS109 MHS110

[1829] MHS111 F 3 C \ < ^ / CF 3

[1830] F3C I^ J CF3

[1831] 15

[1832] / 7— Si— ( \

[1833] \ _ / I \ _ / / y- si— ( / / - Cl — \

[1834] F3c CF3\ _ / I \ _ / Cl

[1835] ' — ' Cl ' —

[1836] 427-32-7 18766-52-4

[1837] 850-61-3

[1838] MHS112 MHS114

[1839] MHS113

[1840] 20

[1841] 1 /

[1842] ^Sif ^. 0 V

[1843] / V- Si— (}

[1844] \ _ / 1 \ _ /

[1845] / - Cl — \

[1846] 25 —Si — —Si — 0 ^0

[1847] 3014489-82-5 0^3 1401585-12-3 3025705-57-8 MHS116

[1848] MHS115 MHS117

[1849] 30 0 CH

[1850] Xj u

[1851] / V- Si — ( > / V- Si— Cl / V- Si— Cl \ _ / I \ /

[1852] Cl

[1853] 2413182-86-0 °0

[1854] 35

[1855] MHS150

[1856] 2413182-87-1 2413182-91-7

[1857]

[1858] MHS151 MHS152 Foreignfiling_text P24-256.docx

[1859] - 149 -

[1860] 5

[1861] 10

[1862] 15

[1863] 20

[1864]

[1865] 25 5) DiHalogenSilane DHS DiHalogenGermane DHG:

[1866] Cl x Cl,

[1867] I

[1868] — Si— \ )— S Ii— ( /

[1869] I

[1870] Cl / 1 C I l \ x Cl 75-78-5 7751-38-4 18395-90-9 30 DHS1 DHS2 DHS3, - x Cl Cl / \ I

[1871] < )— Si— < / r~ Si— \ _ / I O K ) V / I Cl Cl 5578-42-7 18035-74-0 18301-58-1

[1872]

[1873] DHS4 DHS5 DHS6 35 Foreignfiling_text P24-256.docx

[1874] - 150 -

[1875] \ / ci V _^Si Y 1 Si^ ^si^ ^Si^

[1876] / Si

[1877] cr x ci I cr x ci Cl 2406-33-9

[1878] 5 2406-34-0 18420-19-4 DHS50 DHS51 DHS75 F F

[1879] r, - & Cl \ — / Cl

[1880] / A I \ / f / —

[1881] / \ I Cl \ 7— Si — F— < z Si—

[1882] \ _ / I \ _ / I / \ / S‘ —

[1883] Cl / — \ Cl z X= / Cl 10 149-74-6 F F 17983-53-8 DHS100 21980-43-8 DHS102 DHS101

[1884] F

[1885] 15 I T

[1886] 9 O x / Cl Cl— Si-CI Cl— Si-CI Si ci

[1887] Ö F I I

[1888] '^ y xX ' F

[1889] F

[1890] 80-10-4 18030-58-5 20 20160-45-6

[1891] DHS103 DHS105 DHS104

[1892] Cl / =

[1893] 25 Cl \ J

[1894] . Si \ ^s Ii— < / y \

[1895] — Si^ Cl ' - I

[1896] 150529-20-7 Cl— Si-CI DHS107

[1897] 30 18414-36-3 66107-25-3

[1898]

[1899] DHS106 DHS108

[1900] 35 Foreignfiling_text P24-256.docx

[1901] - 151 -

[1902] 5

[1903] 10

[1904] 15

[1905] 20

[1906] 25

[1907] 30

[1908] 35

[1909]

[1910] Foreignfiling_text P24-256.docx

[1911] - 152 -

[1912] 5

[1913] Cl

[1914] 71-55-6 Cl

[1915] Cl THS1 18171-74-9

[1916] 18151-53-6 THS2

[1917] THS3 10

[1918] Cl— Si-CI Cl— Si-CI I I

[1919] Cl Cl 14579-03-4 98-12-4 2407777-16-4 15 THS4 THS5 THS6

[1920] Cl— Si-CI I 20 I Cl Cl

[1921] 18245-29-9 60812-91-1

[1922] THS7 THS8

[1923] 25

[1924] Cl— Si-CI Cl— Si-CI

[1925] I I

[1926] Cl Cl

[1927] 72190-63-7 98-13-5

[1928] 30 THS76 THS100

[1929]

[1930] 35 Foreignfiling_text P24-256.docx

[1931] - 153 -

[1932] 5

[1933] Cl— Si— Cl. 0.

[1934] I ' Cl— Si-CI '

[1935] Cl I ci— J;i— ci Cl c Ji 17902-75-9 107742-40-5 17886-89-4 THS102 THS103

[1936] THS 104 10

[1937] < ci / \ I 15 < z Si-CI I \ / I ci— S i-CI Cl x= / Cl I C I 841313-84-6 70402-93-6 70402 -92-5 THS106 THS107 THS 105

[1938] 20

[1939] ciS^

[1940] I

[1941] 25 Cl— Si— Cl Cl

[1942] I

[1943] Cl 18030-62-1

[1944] 2832113-54-7 THS109

[1945] THS108

[1946] 30

[1947] CI-Ge-CI

[1948] I Cl-G e-CI

[1949] Cl CI-Ge-CI 993-10-2 C;i

[1950] 1184-92-5 Cl THG1

[1951] 13892-15-4 TH G2

[1952] 35

[1953]

[1954] THG3 Foreignfiling_text P24-256.docx

[1955] - 154 -

[1956] F

[1957] 5

[1958] Cl-Ge-Cl

[1959] I CI

[1960] 19089-94-2

[1961]

[1962] THG4

[1963] 10

[1964] B Representation of the synthons S:

[1965] Example S1

[1966] 15

[1967]

[1968] 800 ml n-heptane are mixed with 3.3 g (5 mmol) B is[( 1,2, 5,6-r|)-1,5-cyclo-octadiene]di-p-methoxydi-iridium(l) [12148-71-9], then with 2.7 g (10 mmol) 20 4,4'-Di-tert-butyl-[2,2']bipyridinyl [72914-19-3] and then with 5.1 g (10 mmol) Bis-(pincolato)diborane and stirred for 15 minutes at room temperature. Then, 127.0 g (500 mmol) of bis(pinacolato)diborane and then 113.2 g (500 mmol) of dispiro[cyclopentane-1,1'-[1H]indene-3'(2'H),1"-cyclopentane] [405281-78-9] are added, and the mixture is heated to 80 °C for 12 hours (TLC-25 control - heptane:ethyl acetate 5:1). After cooling, the reaction mixture is treated with 300 ml of ethyl acetate, filtered through a silica gel bed, and the filtrate is completely concentrated under vacuum. The crude product is recrystallized twice from acetone (approx. 800 ml). Yield: 158.8 g (450 mmol), 90%; purity: approx. 99%. 1 H-NMR.

[1969] 30

[1970] 35

[1971]

[1972] Foreignfiling_text P24-256.docx

[1973] - 155 -

[1974] Procedure analogous to C. Reus et al., J. Org. Chem. 2012, 77, 3518, Verb. 5, Method B. Starting material: 35.2 g (100 mmol) S1a. Yield: 26.1 g (85 mmol), 85%, after bulb distillation; purity 99% according to 1 H-NMR.

[1975] 5

[1976]

[1977] can be.

[1978] Example: Raw material, product

[1979] S2

[1980] 10

[1981] — Br 36726-41-7

[1982] 15 S3

[1983] — Br

[1984]

[1985] 2388979-11-9

[1986] C: Representation of the compounds according to the invention:

[1987] 20 Example B1:

[1988] 25

[1989]

[1990] Representation according to DE4229086, example 2.

[1991] A well-stirred mixture of 108.8 g (404 mmol) EAB1 and 1000 ml diethyl ether, cooled to -78 °C, is treated dropwise with 475.3 ml (808 mmol) tert-butyllithium, 1.7 M in n-hexane. The mixture is stirred for 15 minutes, then heated to 10 °C for 30 minutes. A mixture of 11.5 ml (100 mmol) silicon tetrachloride [10026-04-7] and 100 ml diethyl ether is then slowly added dropwise. After the exothermic reaction has subsided, the mixture is heated under reflux for 2 hours. After cooling, slowly pour into 2 L of ice-cold 2 N hydrochloric acid while stirring well, stir briefly again, separate the organic phase 35, wash it twice with 300 ml of water each time and once with 300 ml of saturated sodium chloride solution, and dry over a mixture of Foreignfiling_text P24-256.docx

[1992] - 156 -

[1993] Magnesium sulfate and potassium carbonate. The mixture is filtered from the drying agent through a silica gel bed and concentrated under vacuum to dryness. Further purification is carried out by repeated hot extraction crystallization (using common organic solvents or combinations thereof, preferably acetonitrile-5 DCM, 1:3 to 3:1 vv) or by chromatography and fractional sublimation or annealing under high vacuum. Yield: 59.1 g (75 mmol), 75%.

[1994] Purity: approx. 99.9% according to HPLC or high-temperature GC.

[1995] Similarly, the following compounds can be represented, if necessary, by adjusting the stoichiometry.

[1996] Example: Raw materials, product

[1997] EAB2

[1998] B2

[1999] 10026-04-7 4

[2000] 15

[2001] Si

[2002] EAB3

[2003] B3

[2004] 10026-04-7 - 4

[2005] 20

[2006] EAB4

[2007] B4

[2008] 10026-04-7

[2009] 4

[2010] 25

[2011] EAB5

[2012] B5

[2013] 10026-04-7

[2014] 30 4

[2015]

[2016] 35 Foreignfiling_text P24-256.docx

[2017] - 157 -

[2018] EAB6

[2019] B6

[2020] 10026-04-7

[2021] 5

[2022] 4

[2023] EAB7

[2024] 10 B7

[2025] 10026-04-7

[2026] 4

[2027] EAB8

[2028] B8

[2029] 10026-04-7

[2030] 15 - 4

[2031] Yes

[2032] EAB1

[2033] B9

[2034] 10038-98-9 4

[2035] Ge

[2036] 20

[2037] EAB8

[2038] B10

[2039] 10038-98-9 4

[2040] Ge

[2041] 25

[2042] AB10

[2043] B100 EMHS1

[2044] 30

[2045] AB12

[2046] B101 EMHS1

[2047] 35

[2048]

[2049] Foreignfiling_text P24-256.docx

[2050] - 158 -

[2051] AB71

[2052] B102 EMHS1

[2053] 5

[2054] Q O 10

[2055] AB30 / Si / B103

[2056] EMHS2

[2057] 15

[2058] AB7

[2059] B104

[2060] EMHS2

[2061] 20

[2062] AB70

[2063] B105 O P

[2064] EMHS2

[2065] 0 ^ 0 25

[2066] Sif. B106

[2067] EMHS3

[2068] 30

[2069]

[2070] 35 Foreignfiling_text P24-256.docx

[2071] - 159 -

[2072] AB35

[2073] B107

[2074] 5 EMHS3

[2075] .w. 10 A ' '

[2076] AB11

[2077] B108

[2078] EMHS3 cpsA 15

[2079] 20 AB53 n 0

[2080] B109

[2081] EMHS3 00 0 25

[2082] AB1

[2083] B110

[2084] EMHS4

[2085] 30

[2086] AB32

[2087] B111

[2088] EMHS4

[2089] 35 7)0 y

[2090]

[2091] Foreignfiling_text P24-256.docx

[2092] - 160 -

[2093] ii—

[2094] AB9

[2095] B112

[2096] 5 EMHS4 / Ov.-

[2097] 10

[2098] AB33 XJ A B113

[2099] EMHS4 F \ ^ 3i CX /

[2100] 15

[2101] AB50

[2102] B114. A y- >

[2103] EMHS5

[2104] 20

[2105] AB5

[2106] B115

[2107] EMHS5

[2108] 25

[2109] / \ D

[2110] 30 AB6

[2111] B116

[2112] EMHS5 /

[2113]

[2114] F / \

[2115] 35 Foreignfiling_text P24-256.docx

[2116] - 161 -

[2117] 5

[2118] 10

[2119] 15

[2120] 20

[2121] 25

[2122] 30

[2123]

[2124] 35 Foreignfiling_text P24-256.docx

[2125] - 162 -

[2126] 5

[2127] 10

[2128] 15

[2129] 20

[2130] 25

[2131] 30

[2132]

[2133] 35 Foreignfiling_text P24-256.docx

[2134] - 163 -

[2135] 5 AB33

[2136] B126 LT OAT?

[2137] ETHS2 F / X / i Xi / r x

[2138] 10

[2139] AB1 XX

[2140] B127

[2141] ETHS2 Ul A X

[2142] 15

[2143] 20

[2144] AB100

[2145] B128

[2146] ETHS1

[2147] 25

[2148] 30 AB101

[2149] B129

[2150] ETHS2 jSSSXc ^~ sj ~c — (Sll

[2151]

[2152] 35 Foreignfiling_text P24-256.docx

[2153] - 164 -

[2154] AB 102

[2155] B130

[2156] 5 ETHS2

[2157] / Os QQ LTLJ 0 10

[2158] yo 0 B131 AB36

[2159] EDHS1

[2160] 15 0 0

[2161] AB54

[2162] 20 B132

[2163] EDHS1

[2164] 25

[2165] AB55

[2166] B133

[2167] EDHS1

[2168] 30

[2169]

[2170] 35 Foreignfiling_text P24-256.docx

[2171] - 165 -

[2172] AB72

[2173] 5 B134 vÖ o EDHS1

[2174] 10

[2175] MHS1

[2176] B135

[2177] EAB5

[2178] "It's—

[2179] I

[2180] 15

[2181] MHS2

[2182] B136

[2183] EAB5 QFZQJRQ D3C — With CiD C3D3

[2184] 20

[2185] MHS3

[2186] B137

[2187] EAB5

[2188] 25 i MHS4

[2189] B138

[2190] EAB5

[2191] 30

[2192] MHS5

[2193] B139

[2194] EAB3

[2195] 35

[2196]

[2197] ^>2c? Foreignfiling_text P24-256.docx

[2198] - 166 -

[2199] MHS6

[2200] B140

[2201] EAB3

[2202] 5

[2203] MHS6 / =\ I B141 \ / — \ / —Si— EAB3

[2204] 10

[2205] MHS8

[2206] B142

[2207] EAB1

[2208] 15

[2209] MHS9

[2210] B143

[2211] EAB1

[2212] 20

[2213] MHS10

[2214] B144

[2215] EAB1

[2216] 25

[2217] MHS11

[2218] B145 (' 7 - \ Si— ( >

[2219] EAB6

[2220] 30

[2221] MHS12

[2222] B146

[2223] EAB8

[2224] 35

[2225]

[2226] Foreignfiling_text P24-256.docx

[2227] - 167 -

[2228] MHS13

[2229] B147

[2230] EAB2

[2231] R

[2232] 5 F

[2233] MHS14

[2234] B148

[2235] EAB50

[2236] 10

[2237] MHS15

[2238] B149

[2239] EAB51

[2240] 15

[2241] Ö x

[2242] MHS52

[2243] B150

[2244] EAB52

[2245] 20 ©

[2246] MHS53

[2247] B151

[2248] EAB58

[2249] 25

[2250] MHS75

[2251] B152 \ ]

[2252] EAB58 —Si- U- 30 / c ■k x

[2253] MHS100

[2254] B153

[2255] EAB55

[2256] 35

[2257]

[2258] Foreignfiling_text P24-256.docx

[2259] - 168 -

[2260] MHS101

[2261] B154

[2262] EAB55

[2263] ot JC)

[2264] MHS102

[2265] B155

[2266] EAB8

[2267] MHS103

[2268] B156

[2269] EAB8

[2270] MHS105

[2271] B157

[2272] EAB7

[2273] MHS106

[2274] B158

[2275] EAB6 \= / yy i w

[2276] MHS107

[2277] B159

[2278] EAB1

[2279] MHS108

[2280] B160

[2281] EAB8

[2282]

[2283] Foreignfiling_text P24-256.docx

[2284] - 169 -

[2285] MHS109 B161 o co c EAB1 I J coo c fl T LL LL o oI fl \ u O MHS110 o c co

[2286] B162

[2287] EAB1

[2288] MHS111

[2289] B163 ^0 cX EAB1

[2290] MHS112

[2291] B164

[2292] EAB1

[2293] E

[2294] / A MHS113 I M Xj B165

[2295] EAB1

[2296] F

[2297] MHS114 y-. Ql B166

[2298] EAB8 ( Y-si— ( >

[2299]

[2300] A r Foreignfiling_text P24-256.docx

[2301] - 170 -

[2302] . -J- MHS115

[2303] B167

[2304] EAB8 - 5

[2305] 10 MHS116

[2306] B168

[2307] EAB1

[2308] 15

[2309] MHS117

[2310] B169 X ( y- sU EAB1 i— (\ ) — <} u

[2311] 20

[2312] MHS150

[2313] B170

[2314] EAB1

[2315] 25

[2316] MHS151 O B171, ( Vf

[2317] EAB8

[2318] 30

[2319] MHS152

[2320] B172

[2321] EAB1

[2322] 35

[2323]

[2324] Foreignfiling_text P24-256.docx

[2325] - 171 -

[2326] MHS153 1 OQ B173

[2327] EAB1

[2328] 5 vO

[2329] MHS154

[2330] B174

[2331] EAB1 10 xO O

[2332] MHS155 X OCYv B175

[2333] 15 EAB1

[2334] MGH1

[2335] 20 B176

[2336] EAB5

[2337] Y r MGH2

[2338] 25 B177

[2339] EAB8 3e —

[2340] 30 MGH3

[2341] B178

[2342] EAB1

[2343] 36— F.. F _ F

[2344]

[2345] F 1

[2346] 35 Foreignfiling_text P24-256.docx

[2347] - 172 -

[2348] MGH4

[2349] B179

[2350] EAB6

[2351] 5

[2352] MGH5

[2353] B180

[2354] EAB8

[2355] 10

[2356] MGH6

[2357] B181

[2358] EAB1

[2359] 15

[2360] DHS1

[2361] B182 < V Si— / >

[2362] EAB8

[2363] 20 Ö DHS2

[2364] B183

[2365] EAB8

[2366] 25

[2367] DHS3

[2368] B184

[2369] EAB1

[2370] 30

[2371] DHS4 z \ 1 / = \ B185

[2372] EAB1

[2373]

[2374] 35 Foreignfiling_text P24-256.docx

[2375] - 173 -

[2376] DHS5

[2377] B186

[2378] EAB1

[2379] 5

[2380] DHS6

[2381] B187

[2382] EAB1

[2383] 10

[2384] DHS50

[2385] 15 B188

[2386] EAB8

[2387] 20

[2388] DHS51

[2389] B189

[2390] EAB8

[2391] / \ z \ 25

[2392] DHS51

[2393] B190

[2394] EAB1

[2395] P vv — v— Si \ / \ / \ 30 _X Q _V DHS100

[2396] B191 < Vsi— ( )

[2397] EAB1

[2398] 1

[2399]

[2400] 35 Foreignfiling_text P24-256.docx

[2401] - 174 -

[2402] F

[2403] DHS101 -X T X X B192

[2404] EAB1 ( Vsi— ( / 5 X / I XX Q0J 4 O

[2405] 10 DHS102

[2406] B193

[2407] EAB1

[2408] 15

[2409] DHS103

[2410] B194 X I EAB1

[2411] x H F

[2412] 20

[2413] X i X X DHS104

[2414] B195 / V-Si— Z y EAB1

[2415] 25 4X X F ^F F

[2416] 30 DHS105

[2417] B196

[2418] EAB8

[2419]

[2420] 35 Foreignfiling_text P24-256.docx

[2421] - 175 -

[2422] DHS106

[2423] B197

[2424] EAB1

[2425] 5

[2426] DHS107

[2427] B198

[2428] 10 EAB1

[2429] — k S iiC V / V 15 DHS108

[2430] B199

[2431] EAB1 / \ / CO GO — — — —

[2432] 20

[2433] DHS109

[2434] B200

[2435] EAB1

[2436] — — S ii- -Si—

[2437] >iJ

[2438] 25

[2439] 4^ DHS110

[2440] B201 Si— ( VSi EAB1

[2441] 30

[2442]

[2443] V

[2444] 35 Foreignfiling_text P24-256.docx

[2445] - 176 -

[2446] DHS111

[2447] B202

[2448] 5 EAB1

[2449] 10 DHG1

[2450] B203

[2451] EAB6

[2452] DGH2

[2453] 15 B204

[2454] EAB6

[2455] DHG3

[2456] B205

[2457] 20 EAB1

[2458] A / 1 / \ \, Si DHG4 >=\ ( I A B207 / Y-Ge-C ) 25 EAB1 \V i ) w -V / Si

[2459] \ I A

[2460] DHG5 -GeZ^ 30 B208

[2461] EAB1

[2462]

[2463] 0A 35 Foreignfiling_text P24-256.docx

[2464] - 177 -

[2465] 5

[2466] 10

[2467] 15

[2468] 20

[2469] 25

[2470] 30

[2471] 35

[2472]

[2473] Foreignfiling_text P24-256.docx

[2474] - 178 -

[2475] 5

[2476] 10

[2477] 15

[2478] 20

[2479] 25

[2480] 30

[2481]

[2482] 35 Foreignfiling_text P24-256.docx

[2483] - 179 -

[2484] 5

[2485] 10

[2486] 15

[2487] 20

[2488] 25

[2489] 30

[2490] 35

[2491]

[2492] Foreignfiling_text P24-256.docx

[2493] - 180 -

[2494] 5

[2495] 10

[2496] 15

[2497] 20

[2498] 25

[2499] 30

[2500] 35

[2501]

[2502] Foreignfiling_text P24-256.docx

[2503] - 181 -

[2504] THS108

[2505] B230 Sr- 5 EAB1

[2506] 10

[2507] THS109

[2508] B231

[2509] EAB1

[2510] 15

[2511] ? / S I i \ / == / ^ THS61

[2512] B232

[2513] EAB8

[2514] 20

[2515] — c; H- THS62

[2516] 25 B233

[2517] EAB8

[2518] 30

[2519] THG3

[2520] B234

[2521] EAB1

[2522]

[2523] 35 Foreignfiling_text P24-256.docx

[2524] - 182 -

[2525] THG4

[2526] B235

[2527] 5 EAB1

[2528] 10

[2529] ETHS1

[2530] B236

[2531] S1 Q 15

[2532] 20 ETHS1

[2533] B237

[2534] S2

[2535] 25

[2536] ETHS1

[2537] B238

[2538] 30 S3

[2539]

[2540] 35 Foreignfiling_text P24-256.docx

[2541] – 183 –

[2542] EAB100

[2543] B239 Yes- 10026-04-7

[2544] 5 years—

[2545] 4 residues- EAB101

[2546] B300 Si- 10026-04-7

[2547] 10 Yes—

[2548] 4

[2549] EAB102

[2550] B301 Si- 15 10026-04-7 / — F If—

[2551] 4

[2552] EAB103

[2553] B302 Si- 20 10026-04-7

[2554] / S ^~ 4 \E- EAB104

[2555] 25 B303 Si- 10026-04-7

[2556] / Si—

[2557] 4

[2558] 30 EAB105

[2559] B304 Yes—

[2560] 10026-04-7

[2561]

[2562] 4

[2563] 35 Foreignfiling_text P24-256.docx

[2564] – 184 –

[2565] EAB106

[2566] B305

[2567] 10026-04-7 Si- 5

[2568] SP—

[2569] 4

[2570] ) OT − − /

[2571] EAB107

[2572] 10 B306

[2573] 10026-04-7 o / x We-

[2574] -x Q

[2575] 15 EMHS2

[2576] B307 / si— and EAB101

[2577] ' or r- 20

[2578] si— EMHS5

[2579] B308

[2580] EAB106

[2581] 25

[2582] EMHS100

[2583] B309

[2584] 30 EAB104

[2585]

[2586] 35 Foreignfiling_text P24-256.docx

[2587] - 185 -

[2588] ~- \sj / " VS \ /

[2589] EMHS100 B310

[2590] EAB105

[2591] L / V

[2592] EMHS100

[2593] B311

[2594] EAB106

[2595] — S< / SH- \ / T V \ / —-Si { J Si—

[2596] / ' 2?^ EMHS100

[2597] B312

[2598] EAB106

[2599] " I'X

[2600] MHS53

[2601] B313

[2602] EAB106

[2603] / S *C

[2604] MHS107

[2605] B314 cX o

[2606] EAB107

[2607]

[2608] '\ '\ Foreignfiling_text P24-256.docx

[2609] - 186 -

[2610] 5

[2611] 10

[2612] 15

[2613] 20

[2614] 25

[2615] 30

[2616]

[2617] 35 Foreignfiling_text P24-256.docx

[2618] - 187 -

[2619] 5

[2620] 10

[2621] 15

[2622] 20

[2623] 25

[2624] 30

[2625]

[2626] 35 Foreignfiling_text P24-256.docx

[2627] - 188 -

[2628] U I

[2629] DHG7

[2630] B325

[2631] 5 EAB101 qf Vv — S

[2632] Xx l?15^ 0i^^^sl

[2633] — sf \ L / J 'sH- 10

[2634] B326 THS8

[2635] EAB101

[2636] i: : S —Si Si / \ I 15

[2637] i 'Ty THS105

[2638] B327 Z V- Si-Y y EAB101

[2639] 20

[2640] - s q /

[2641] si '^ siC"

[2642] 25 THS107

[2643] B328

[2644] EAB101

[2645] —Si— f |l

[2646] \\ 1 1 / >i Sif

[2647] 30

[2648] THS109

[2649] B329

[2650] EAB107

[2651] 35

[2652]

[2653] Foreignfiling_text P24-256.docx

[2654] - 189 -

[2655] AB10

[2656] B330 EMHS100

[2657] 5, A Av _ / / \ l /

[2658] 10

[2659] AB30 A B331

[2660] EMHS100 'c Si \

[2661] 15 x sr-s<

[2662] AB7

[2663] B332 / Si /

[2664] EMHS100

[2665] 20

[2666] W

[2667] AB70 4' 25 B333

[2668] EMHS

[2669] 30

[2670] AB11 A x. / B334

[2671] EMHS3

[2672] 35

[2673]

[2674] Foreignfiling_text P24-256.docx

[2675] - 190 -

[2676] AB53

[2677] B335

[2678] 5 EMHS100

[2679] ^sr'sn- 10

[2680] AB1

[2681] B336

[2682] EMHS100

[2683] w

[2684] 15 X 'Si^ X 'Si—

[2685] AB32

[2686] B337 / . Si /

[2687] EMHS100

[2688] TyJ r 20

[2689] -SiG

[2690] Ast' I J Si— AB9

[2691] B338

[2692] 25 EMHS100

[2693] ' '

[2694] 30

[2695] AB33

[2696] B339

[2697] EMHS100

[2698]

[2699] 35 Foreignfiling_text P24-256.docx

[2700] - 191 -

[2701] \ I

[2702] Yes Yes—

[2703] AB50

[2704] B340 1 Yes / 5 EMHS100

[2705] / =<

[2706] \ K /

[2707] Yes Yes—

[2708] 10

[2709] AB5

[2710] B341 ^ 1X DJL. Yes _ /

[2711] EMHS100

[2712] YX Fr s< / x \ ^sr / XD x 15

[2713] THDS1

[2714] B400 / Yes Yes EAB1

[2715] 20

[2716] THDS2

[2717] 25 B401 Yes Yes EAB1

[2718] 30 \ / ^ > Ph Ph / \t /

[2719] THDS3 XM HV t B402 / Yes Yes EAB1

[2720] 35

[2721]

[2722] Foreignfiling_text P24-256.docx

[2723] - 192 -

[2724] THDS4

[2725] B403 z Yes Yes EAB1

[2726] 5

[2727] 10 THDS1

[2728] B404 ^ jSi Si ^

[2729] EAB8

[2730] 15

[2731] THDS2

[2732] B405 Si Si EAB8

[2733] 20

[2734] 25 THDS3

[2735] B406 Si Si EAB8

[2736] _ AA lV> Ph Ph K\VA A V / —

[2737] 30

[2738] THDS4

[2739] B407 ^Maybe You EAB8

[2740] 35

[2741]

[2742] Foreignfiling_text P24-256.docx

[2743] - 193 - X SK ^SiC

[2744] ^j / / x1 Z) W (on ci THDS1

[2745] B408

[2746] EAB100 ) \XL \XT (V V'' " xr / ö / \

[2747] Yes 1 X 'p < z \ J= - — JL x x sr / \ / _ \ / / °- w 11

[2748] "vT^"

[2749] THDS2

[2750] B409

[2751] EAB100 x-^ H m

[2752] si^ ^sr z \ \

[2753] THDS3

[2754] B410

[2755] EAB100

[2756] THDS4

[2757] B411

[2758] EAB100

[2759] HHDS1

[2760] B412

[2761] EAB1

[2762]

[2763] Foreignfiling_text P24-256.docx

[2764] - 194 -

[2765] HHDS2

[2766] B413

[2767] EAB1

[2768] 5 ^0 V m

[2769] 10 HHDS3

[2770] B414

[2771] EAB1 j\ Oj* \O~Y

[2772] 15

[2773] HHDS4

[2774] B415

[2775] EAB1 jKJHAZAA ) / '.

[2776] 20 ^ Q, A / X

[2777] 25 HHDS1 VA _ bPr B416

[2778] EAB8

[2779] AAPL

[2780]

[2781] 30

[2782] 35 Foreignfiling_text P24-256.docx

[2783] - 195 -

[2784] 5 HHDS3

[2785] B317

[2786] EAB8 C ^ -si — si ~ cy

[2787] 10 \ on

[2788] \ If^ _-If i ~^X \ / Y Si \ \. U VJ ( HHDS1 Si h \ \ / — \ / / — \ Si B418

[2789] EAB100 \ < H \\ r S H ) / x 15 ' 1 XX CX /

[2790] / \ k / If x / sr ^Yes ^ \

[2791] / \

[2792] \ _S in i ( V si 7 20

[2793] HHDS3

[2794] B419

[2795] EAB100 < TH — K IT 7 \ 1 X l \ k\ z X

[2796] 25

[2797]

[2798] / \

[2799] 30

[2800]

[2801] Preparation according to JP11322935, Example 1. Purification as described in B1 35. Starting material: 39.1 g (100 mmol) EMHS2, yield: 28.0 g (38 mmol) 76%. Purity: approx. 99.9% by HPLC or high-temperature GC. Foreignfiling_text P24-256.docx

[2802] - 196 -

[2803] The following connections can be represented analogously.

[2804] Example: Raw materials, product

[2805] 5

[2806] B501 EMHS3

[2807] 10

[2808] \ XU A. B502 EMHS4 TQ AU 15 YV S L OA i O\~A / '

[2809] 20

[2810] B503 EMHS5

[2811] PA jtxp

[2812] 25

[2813] EMHS2

[2814] 50 mmol

[2815] B504

[2816] / Y-Si — 0 — Si— EMHS5

[2817] 50 mmol

[2818] 30

[2819]

[2820] 35 Foreignfiling_text P24-256.docx

[2821] - 197 -

[2822] 5

[2823]

[2824] 10 D: Production of mixtures: PreMix

[2825] Example: PreMixI

[2826] A mixture of 7.5 g HTM [136463-07-5], vacuum TGA (5 wt% - actual): 211 °C, see Table 4, and 2.5 g B6, vacuum TGA (5 wt% - actual): 212 °C, is carefully melted in a Schlenk tube under argon without overheating the melt. After homogenization, the melt is allowed to cool, and the resulting organic glass is pulverized. In this form, it is used as PreMix1 for the production of OLED components.

[2827] 20 E: Device examples for blue fluorescent OLEDs

[2828] In the following examples, OLEDs according to the invention (examples Ba1 to Ba4, Bb1 to Bb11 and Bc1) and one OLED according to the prior art (comparative example Va1, Vb1 or Vc1) are produced. The exact structure of the OLEDs can be found in Tables 1, 2 and 3. The 25 materials used to produce the OLEDs are shown in Table 4. The properties of the OLEDs according to the invention of examples Ba1 to Ba4, Bb1 to Bb11 and Bc1 and the properties of the OLEDs according to the prior art are listed in Tables 5, 6 and 7.

[2829] 30 Manufacturing of OLEDs

[2830] Glass plates coated with structured ITO (indium tin oxide) of 50 nm thickness are used as a substrate for the OLEDs.

[2831] All materials are thermally vapor-deposited in a vacuum chamber.

[2832] 35 The emission layer always consists of at least one matrix material (also called host material) and an emitting foreignfiling_text P24-256.docx

[2833] - 198 -

[2834] A dopant (doping agent, emitter) is added to the matrix material(s) by cover evaporation in a specific volume fraction. A specification such as BH:BD (97:3) 20 nm means that the material BH is present as the host material in a volume fraction of 97%, and the compound BD is present in a volume fraction of 3% in a 20 nm thick layer. Similarly, the hole injection layer (HIL), the hole transport layer (HTL), and / or the electron transport layer (ETL) can also consist of a mixture of two or more materials. The structure of the respective OLEDs is shown in Tables 1, 2, and 3.

[2835] 10

[2836] Table 1:

[2837] HIL HTL EBL EML HBL ETL EIL

[2838] Bsp.

[2839] Dicke Dicke Dicke Dicke Dicke Dicke Dicke HTM1: PD BH: BD ETM1: LiQ HTM1 EBM HBM LiQ Va1 (95:5) (97:3) (50:50)

[2840] 15 175 nm 5 nm 5 nm 2 nm 10 nm 20 nm 33 nm HTM1: PD BH: BD ETM1: B1 HTM1 EBM HBM LiQ Ba1 (95:5) (97:3) (50:50)

[2841] 175 nm 5 nm 5 nm 2 nm 10 nm 20 nm 33 nm HTM1: PD BH: BD ETM1: B1: LiQ HTM1 EBM HBM LiQ Ba2 (95:5) (97:3) (50:25:25)

[2842] 20 175 nm 5 nm 5 nm 2 nm 10 nm 20 nm 33 nm HTM1: PD BH: BD ETM2: B10

[2843] HTM1 EBM HBM LiQ Ba3 (95:5) (97:3) (50:50)

[2844] 175 nm 5 nm 5 nm 2 nm 10 nm 20 nm 33 nm HTM1: PD BH: BD ETM3: B120

[2845] HTM1 EBM HBM LiQ Ba4 (95:5) (97:3) (40:60)

[2846] 175 nm 5 nm 5 nm 2 nm 25

[2847]

[2848] 10 nm 20 nm 33 nm

[2849] Table 2:

[2850] HIL HTL EBL EML HBL ETL EIL

[2851] Bsp.

[2852] Dicke Dicke Dicke Dicke Dicke Dicke Dicke HTM1: PD BH: BD ETM1: LiQ

[2853] 30 HTM1 EBM HBM LiQ Vb1 (95:5) (97:3) (50:50)

[2854] 180 nm 5 nm 5 nm 2 nm 10 nm 20 nm 30 nm HTM1: PD HTM1: B1 BH: BD ETM1: LiQ EBM HBM LiQ Bb1 (95:5) (70:30) (97:3) (50:50)

[2855] 5 nm 5 nm 2 nm 10 nm 180 nm 20 nm 30 nm HTM1: PD HTM1: B8 BH: BD ETM4: LiQ

[2856] 35 EBM HBM LiQ Bb2 (95:5) (70:30) (97:3) (50:50)

[2857] 5 nm 5 nm 2 nm

[2858]

[2859] 10 nm 180 nm 20 nm 30 nm Foreignfiling_text P24-256.docx

[2860] - 199 -

[2861] HTM1: PD HTM1: B105 BH: BD ETM1: LiQ EBM HBM LiQ Bb3 (95:5) (70:30) (97:3) (50:50)

[2862] 5 nm 5 nm 2 nm 10 nm 180 nm 20 nm 30 nm HTM1: PD HTM2: B130 BH: BD ETM1: LiQ EBM HBM LiQ Bb4 (95:5) (70:30) (97:3) (50:50)

[2863] 5 nm 5 nm 2 nm 5 10 nm 180 nm 20 nm 30 nm HTM1: PD HTM1: B174 BH: BD ETM1: LiQ EBM HBM LiQ Bb5 (95:5) (70:30) (97:3) (50:50)

[2864] 5 nm 5 nm 2 nm 10 nm 180 nm 20 nm 30 nm HTM1: PD HTM1: B236 BH: BD ETM1: LiQ EBM HBM LiQ Bb6 (95:5) (70:30) (97:3) (50:50)

[2865] 5 nm 5 nm 2 nm 10 10 nm 180 nm 20 nm 30 nm HTM1: PD HTM1: B305 BH: BD ETM1: LiQ EBM HBM LiQ Bb7 (95:5) (70:30) (97:3) (50:50)

[2866] 5 nm 5 nm 2 nm 10 nm 180 nm 20 nm 30 nm HTM1: PD HTM1: B400 BH: BD ETM1: LiQ EBM HBM LiQ Bb8 (95:5) (70:30) (97:3) (50:50)

[2867] 5 nm 5 nm 2 nm 10 nm 180 nm 20 nm 30 nm

[2868] 15 HTM1: PD HTM3: B412 BH: BD ETM1: LiQ EBM HBM LiQ Bb9 (95:5) (75:25) (97:3) (50:50)

[2869] 5 nm 5 nm 2 nm 10 nm 180 nm 20 nm 30 nm HTM1: PD HTM1: B418 BH: BD ETM1: LiQ EBM HBM LiQ Bb10 (95:5) (75:25) (97:3) (50:50)

[2870] 5 nm 5 nm 2 nm 10 nm 180 nm 20 nm 30 nm

[2871] 20 HTM1: PD HTM1: B503 BH: BD ETM4: LiQ EBM HBM LiQ Bb11 (95:5) (70:30) (97:3) (50:50)

[2872] 5 nm 5 nm 2 nm

[2873]

[2874] 10 nm 180 nm 20 nm 30 nm

[2875] Tabelle 3:

[2876] HIL HTL EBL EML HBL ETL EIL

[2877] 25 Bsp.

[2878] Dicke Dicke Dicke Dicke Dicke Dicke Dicke HTM1: PD BH: BD ETM1: LiQ HTM1 EBM HBM LiQ Vc1 (95:5) (97%:3%) (50:50)

[2879] 183 nm 5 nm 5 nm 2 nm 10 nm 20 nm 34 nm HTM1: PD HTM1: B1 BH: BD ETM1: B1

[2880] EBM HBM LiQ Bc1 (95:5) (70:30) (97%:3%) (50:50)

[2881] 5 nm 5 nm 2 nm 30

[2882]

[2883] 10 nm 183 nm 20 nm 34 nm

[2884] Tabelle 4: OLED-Materialien

[2885] 35 Foreignfiling_text P24-256.docx

[2886] - 200 -

[2887] Q0 F

[2888] \ xCN

[2889] FVO O NC. AO U F

[2890] I Iy F

[2891] ^ / F \\ F F \7 5 YA

[2892] AI the A

[2893] , / F k

[2894] IV yv CN

[2895] F ^ll O. J / A

[2896] F CN / / Q /

[2897] QLJJ >

[2898] NCZ p r

[2899] FOR PD Ö Q< M u [1224447-88-4] HTM1 [136463-07-5]

[2900] O o

[2901] 10 J

[2902] 15

[2903] HTM2 [1364603-07-5] HTM3 [2356086-92-3] Li'-O QA

[2904] 20 Q y

[2905] EBM LiQ [25387-93-3]

[2906] 25 uO

[2907] O ^OuCuuc

[2908] BH [1087346-88-0] BD [1182175-27-4] 30

[2909] rv< A N =< 35 0 U <0

[2910]

[2911] HBM [1955543-57-3] ETM1 [2173328-31-7] Foreignfiling_text P24-256.docx

[2912] -201 -

[2913] 5

[2914] 10

[2915] 15

[2916] 20

[2917] 25

[2918]

[2919] 30

[2920] 35 Foreignfiling_text P24-256.docx

[2921] -202 -

[2922] 5

[2923] 10

[2924] 15

[2925] 20

[2926] 25

[2927] 30

[2928] B412

[2929] 35

[2930]

[2931] Foreignfiling_text P24-256.docx

[2932] -203 -

[2933] 5

[2934]

[2935] Characterization of OLEDs

[2936] 10

[2937] The OLEDs are characterized according to standard procedures. For this, the electroluminescence spectra and current-voltage-luminance characteristics (IIIL characteristics) are measured, and the efficiency is calculated from these measurements. The calculation is performed assuming a Lambertian emission characteristic. The electroluminescence spectra are measured at a luminous flux of 15°C.

[2938] density of 1000 cd / m² 2 The color coordinates of the CIE 1931 x and y colorimetric values ​​were determined and calculated from them. The voltage required for a current density of 10 mA / cm² was then used. 2 The required value is denoted here as U10. EQE10 denotes the external quantum efficiency at a current density of 10 mA / cm². 2 .

[2939] 20

[2940] For each example, the relative EQE and the relative voltage are calculated in comparison to the respective reference example:

[2941] rel. U (Ex) = (U10(Ex) / U10(V))

[2942] rel. EQE (Ex) = (EQE10(Ex) / EQE10(V))

[2943] 25

[2944] The refractive index (RI) of a layer at a wavelength of 620 nm is determined using ellipsometry (JA Wollam Inc., USA). The measurement covers the wavelength range from 250 nm to 1000 nm, and the respective refractive index is determined via the dispersion curve. The samples for determining the refractive index (RI) are coated on SiO230

[2945] Substrates with three different layer thicknesses were produced. The respective material was thermally vapor-deposited. From these measurements, the average refractive index for each material or material mixture was determined.

[2946] 35

[2947] The results are presented in Tables 5, 6, and 7 below. Foreignfiling_text P24-256.docx

[2948] - 204 -

[2949] Properties of OLEDs

[2950] Table 5: Properties of O LEDs

[2951] relative

[2952] Relative CIE x / y at RI ETL*

[2953] EQE10

[2954] game U10 (%) 1000 cd / m 2 @ 620 nm

[2955] 5 (%)

[2956] Va1 1.00 1.00 0.14 / 0.13 1.69

[2957] Ba1 1.03 1.06 0.14 / 0.14 1.63

[2958] Ba2 1.01 1.03 0.14 / 0.14 1.66

[2959] Ba3 1.03 1.05 0.14 / 0.14 1.65

[2960] 10

[2961] Ba4 1.01 1.08 0.14 / 0.14 1.62

[2962] (* of the complete E:TL layer of the OLED)

[2963] Table 6: Properties of OLEDs

[2964] 15 relatively

[2965] In relative e

[2966] CIE x / y at RI HTL*

[2967] EQE10

[2968] game U10 (%) (%) 1000 cd / m 2 @ 620 nm

[2969] Vb1 1.00 1.00 0.14 / 0.14 1.73

[2970] Bb1 1.02 1.04 0.14 / 0.13 1.70

[2971] 20 Bb2 1.02 1.06 0.14 / 0.13 1.68

[2972] Bb3 1.01 1.02 0.14 / 0.13 1.71

[2973] Bb4 1.03 1.05 0.14 / 0.13 1.69

[2974] Bb5 1.04 1.01 0.14 / 0.14 1.71

[2975] Bb6 1.03 1.07 0.14 / 0.13 1.68

[2976] 25

[2977] Bb7 1.03 1.09 0.14 / 0.13 1.67

[2978] Bb8 1.03 1.10 0.14 / 0.13 1.67

[2979] Bb9 1.03 1.08 0.14 / 0.13 1.68

[2980] Bb10 1.03 1.09 0.14 / 0.13 1.68

[2981] 30 Bb11 1.02 1.10 0.14 / 0.13 1.67

[2982] (* of the complete HTL layer of the OLED)

[2983] Table 7: Properties of OLEDs

[2984] relative

[2985] 35 Relative CIE x / y at RI HTL* RI ETL*

[2986] EQE10

[2987] game U10 (%) (%) 1000 cd / m 2 @ 620 nm @ 620 nm

[2988]

[2989] Foreignfiling_text P24-256.docx

[2990] -205 -

[2991] V1 1.00 1.00 0.14 / 0.14 1.73 1.71 Bc1 1.04 1.08 0.14 / 0.14 1.70 1.63

[2992]

[2993] (* of the entire layer of the OLED - ETL or HTL)

[2994] 5

[2995] Comparing the inventive examples Ba1 to Ba4, Bb1 to Bb11 and Bc1 with the corresponding comparative examples Va1, Vb1 or Vc1, it is evident that the inventive OLED exhibits a significant advantage in device efficiency, without negatively affecting lifetime, voltage and color. This can be attributed to the lower 10

[2996] The refractive index of the materials according to the invention can be attributed to, for example, the refractive index of B1 is 1.54. The other compounds according to the invention have similar refractive indices. In comparison, LiQ in comparative examples Va1 and Vc1 has a refractive index of 1.65, and the HTM in comparative examples Vb1 and Vc1 has a

[2997] 15

[2998] Refractive index of 1.73.

[2999] Q: Device examples for green phosphorescent OLEDs

[3000] In the following three examples, OLEDs according to the invention (examples gB1a-c, gB2a-b, gB3a and gB4a) and one OLED according to the 20 are described.

[3001] The prior art (comparative examples gV1, gV2, gV3 and gV4) is shown. The exact structure of the OLEDs is given in Table 8. Table 9 shows the materials used to manufacture the OLEDs, in addition to those already shown. The properties of the OLEDs according to the invention, as shown in the examples and comparative examples, are given in Table 25.

[3002] 10 summarized.

[3003] Production of green OLEDs

[3004] The substrate for the OLEDs consists of glass plates coated with a 50 nm thick, structured ITO (indium tin oxide). Every 30

[3005] Materials are thermally vapor-deposited in a vacuum chamber. The emission layer always consists of at least one matrix material (also called host material) and an emitting dopant (doped, emitter), which is added to the matrix material(s) by cover vapor deposition in a specific volume fraction. A 35

[3006] Specifications like GH1: GH2: GE (32:60:8) mean that material GH1 is present in a volume fraction of 32% as host material 1, GH2 in a foreign filing_text P24-256.docx

[3007] -206 -

[3008] The host material 2 comprises 60% by volume, and the compound GE is present in a volume fraction of 8%. Similarly, the hole injection layer (HIL), the hole transport layer (HTL), the electron blocking layer (EBL), the hole blocking layer (HBL), and / or the electron transport layer (ETL) can also consist of a mixture of two or more materials.

[3009] The structure of the respective OLEDs is shown in Table 8, and materials for green OLEDs are shown in Table 9. After the electron injection layer (EIL) is deposited, a 100 nm thick aluminum cathode is deposited onto each component.

[3010] 10

[3011] Table 8: Structure of green OLEDs

[3012] HIL HTL EBL EML HBL ETL EIL

[3013] Example.

[3014] Thickness Thickness Thickness Thickness Thickness Thickness HTM6: PD GH1: GH2: GE ETM5: LiQ

[3015] 15 HTM6 HTM6 HBM LiQ gvi (95:5) (32:60:8) (50:50)

[3016] 50 nm 30 nm 5 nm 3 nm 10 nm 35 nm 30 nm HTM6: PD HTM6: B8 GH1: GH2: GE ETM5: LiQ HTM6 HBM LiQ gB1a (95:5) (70:30) (32:60:8) (50:50)

[3017] 30 nm 5 nm 3 nm 10 nm 50 nm 35 nm 30 nm HTM6: PD HTM6: B8 GH1: GH2: GE ETM5: LiQ HTM6 HBM LiQ 20 gB1b (95:5) (70:30) (32:60:8) (50:50)

[3018] 50 nm 5 nm 3 nm 10 nm 30 nm 35 nm 30 nm HTM6: PD HTM6: B8 HTM6: B8 GH1: GH2: GE ETM5: LiQ

[3019] HBM LiQ gB1c (95:5) 10 (70:30) (70:30) (32:60:8) (50:50)

[3020] 5 nm 3 nm nm 50 nm 30 nm 35 nm 30 nm HTM6: PD GH1: GH2: GE ETM2: LiQ HTM6 HTM5 HBM LiQ gV2 (95:5) (32:60:8) (50:50)

[3021] 25 50 nm 30 nm 5 nm 3 nm 10 nm 35 nm 32 nm HTM6: PD GH1: GH2: GE ETM2: B120: LiQ HTM6 HTM5 HBM LiQ gB2a (95:5) (32:60:8) (50:45:5)

[3022] 50 nm 30 nm 5 nm 3 nm 10 nm 35 nm 32 nm HTM6: PD HTM5: B120 GH1: GH2: GE ETM2: B120: LiQ HTM6 HBM LiQ gB2b (95:5) (70:30) (32:60:8) (50:45:5)

[3023] 30 50 nm 5 nm 3 nm 10 nm 30 nm 35 nm 32 nm HTM6: PD GH1: GH2: GE ETM3: LiQ HTM6 HTM5 HBM LiQ gV3 (95:5) (32:60:8) (50:50)

[3024] 50 nm 30 nm 5 nm 3 nm 10 nm 35 nm 32 nm HTM6: PD GH1: GH2: GE ETM3: B305

[3025] HTM6 HTM5 HBM LiQ gB3a (95:5) (32:60:8) (50:50)

[3026] 50 nm 30 nm 5 nm 3 nm 35 nm 10 nm 35 nm 32 nm HTM2: PD HTM2 HTM4 GH1: GH2: GE HBM ETM4: LiQ LiQ gV4

[3027]

[3028] (95:5) 50 nm 30 nm (32:60:8) 7 nm (50:50) 3 nm Foreignfiling_text P24-256.docx

[3029] -207-

[3030] 10 nm 35 nm 25 nm HTM2: PD HTM2: B400 GH1: GH2: GE ETM4: LiQ HTM4 HBM LiQ gB4a (95:5) (70:30) (32:60:8) (50:50)

[3031] 30 nm 7 nm 3 nm

[3032]

[3033] 10 nm 50 nm 35 nm 25 nm

[3034] 5

[3035] Tabelle 9: OLED Material - new OLEDs

[3036] Material color OLEDs in tabelle 4) _

[3037] QL

[3038] qpd

[3039] 10 QO H

[3040] ? Vy, i

[3041] w ( V4- ^0

[3042] HTM4 HTM5

[3043] 15 £

[3044] Md 0! L

[3045] CrO o

[3046] 20

[3047] HTM6 GH1

[3048] po

[3049] N-0,

[3050] J' J

[3051] 25 a -f- CI xy — (, p

[3052] 0bf \ s 7

[3053] 0 ff — (\ / / ) \ / o

[3054] \ 0D

[3055] _ v XD

[3056] _ /

[3057] 30 >=<

[3058] OO DM D D

[3059]

[3060] GH2 GE

[3061] 35 Foreignfiling_text P24-256.docx

[3062] -208 -

[3063] 5

[3064]

[3065] Characterization of green phosphorescent OLEDs

[3066] 10

[3067] The OLEDs are characterized using standard procedures. This is done analogously to the characterization of the blue OLEDs. The results are summarized in Table 10.

[3068] Table 10: Properties of OLEDs

[3069] 15

[3070] relative relative CIE x / y at

[3071] Example

[3072] U10 EQE10 1000 cd / m 2

[3073] gV1 1.00 1.00 0.34 / 0.64

[3074] gB1a 1.01 1.04 0.34 / 0.64

[3075] 20 gB1b 1.01 1.05 0.34 / 0.64

[3076] gB1c 1.02 1.08 0.34 / 0.64

[3077] gV2 1.00 1.00 0.36 / 0.61

[3078] gB2a 1.02 1.04 0.36 / 0.61

[3079] gB2b 1.02 1.09 0.35 / 0.62

[3080] 25

[3081] gV3 1.00 1.00 0.37 / 0.61

[3082] gB3a 1.03 1.05 0.37 / 0.62

[3083] gV4 1.00 1.00 0.36 / 0.62

[3084] gB4a 1.01 1.05 0.36 / 0.62

[3085]

[3086] 30

[3087] When comparing the examples gB1a-c, gB2a-b, gB3a and gB4a according to the invention with the corresponding comparison examples gV1, gV2, gV3 and gV4, it is evident that the OLEDs according to the invention exhibit a significant advantage in device efficiency, with the lifetime, the 35

[3088] The tension and color will not be negatively affected.

Claims

Foreignfiling_text P24-256.docx -209 - Patent claims 1. Combination of formula (I), 5 R 4 R 1 -M— R 3 R 2 Formula (I) 10 where the following applies to the symbols: M is Si or Ge; R 1 , R 2 , R 3 and R 4 In each occurrence, whether the same or different, 15 is a straight-chain alkyl group with 1 to 40 C atoms, a branched alkyl group with 3 to 40 C atoms, or a cyclic alkyl group with 5 to 40 C atoms, each of which may be substituted with one or more R' and / or Si(R')s substituents, wherein the R substituents 1 , R 2 , R 3 and R 4can also form mono-, bi- and tricyclic rings; a non-condensed aromatic ring system with 6 to 60 aromatic ring atoms or a heteroaromatic ring system with 5 to 60 aromatic ring atoms, which contains at least one heteroatom selected from O and S, wherein the aromatic or heteroaromatic ring system can be substituted with one or more R" groups, an aralkyl group with 7 to 60 C atoms, or OSi(R')3; in which case two or more of the R groups can be 1 , R 2 , R 3 and R 4 be linked together, preferably by a single bond, by an O atom 30 or a CR2 group, and thereby form a ring system; with the proviso that at least one of the residues R 1 , R 2 , R 3 and R 4 corresponds to the following formula (1a), 35 Foreignfiling_text P24-256.docx -210 - 5 Formula (1a) where the dashed line represents the connection to M of formula (I); R is the same or different in each occurrence, a tertiary 10 Alkyl group with 4 to 40 carbon atoms or a neo-alkyl group with 5 to 40 carbon atoms, wherein these groups may each be substituted with one or more D and / or F atoms, a tertiary aralkyl group with 9 to 40 carbon atoms, which may also be substituted with one or more R" residues, or 15 a Si(R')s group; R' is, in each occurrence, either the same or different: a straight-chain alkyl group with 1 to 40 carbon atoms, a branched alkyl group with 3 to 40 carbon atoms, or a cyclic alkyl group with 5 to 20 carbon atoms. 40 C atoms, wherein two R' groups bonding to the same Si atom may also form rings, or an aryl group Ar with 6 to 20 C atoms, wherein the aryl group Ar with one or more substituents selected from straight-chain alkyl groups with 1 to 20 C atoms, branched alkyl groups with 3 25 can be substituted with up to 20 carbon atoms or cyclic alkyl groups with 5 to 20 carbon atoms; R" is the same or different in each occurrence and is chosen from the group consisting of R', D, F, CN and Si(Alkyl)3, 30 where alkyl, whether the same or different, represents an alkyl group with 1 to 10 carbon atoms in each occurrence; R a is the same or different in each occurrence H, D, F or an alkyl group with 1 to 40 C atoms, which is connected to one or more 35 D and / or F atoms, an aryl group Ar with 6 to 40 C atoms or an OSi(R')3 group, can be substituted, wherein Foreignfiling_text P24-256.docx -211 - the aryl group Ar can be substituted with one or more substituents selected from straight-chain alkyl groups with 1 to 20 carbon atoms, branched alkyl groups with 3 to 20 carbon atoms, or cyclic alkyl groups with 5 to 20 carbon atoms, and wherein two residues R a different residues of formula (1a) may also be linked together, preferably by a single bond, by an O atom or a CR₂ group; 10 R b is H, D, F, CN, an alkyl group with 1 to 40 C atoms, an aryl group Ar with 6 to 40 C atoms or an OSi(R')₃ group.

2. Compound according to claim 1, characterized in that the compound of formula (I) has a molecular weight of > 700 g / mol, preferably > 750 g / mol, particularly preferably > 850 g / mol and especially > 900 g / mol.

3. Compound according to claim 1 or 2, characterized in that the compound of formula (I) corresponds to one of the following formulas (IIa) to (IId) 20, 25 30 Formula (IIb) Foreignfiling_text P24-256.docx -212 - 5 10 wherein the symbols have the meanings mentioned in claim 1 15 exhibit.

4. Compound according to one or more of claims 1 to 3, characterized in that M stands for Si. 20 5. Compound according to one or more of claims 1 to 4, characterized in that one, two or three of the groups R 1 , R 2 and R 3 In each occurrence, either the same or different, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a 1-adamantyl group, a neo-pentyl group, an unsubstituted 25 phenyl group or a phenyl group substituted with one or more R" residues.

6. Compound according to one or more of claims 1 to 5, characterized in that R is the same or different in each occurrence. 30 a tert-butyl group, a 1-adamantyl group, a neo-pentyl group, or a trimethylsilyl group.

7. Compound according to one or more of claims 1 to 6, characterized in that R a The same or different for each occurrence 35 H, D or F, preferably H, is and / or that R b at every occurrence Foreignfiling_text P24-256.docx -213 - is the same or different H, D, F, CN or a methyl group, preferably H.

8. Compound according to one or more of claims 1 to 7, characterized in that the remainder of formula (1a) corresponds to one of the following formulas (1b) or (1c) 10 Formula (Ic) 15 where the dashed line denotes the bond to M and the following also applies: R 5 , R 6 and R 7 is the same or different in each occurrence, 20 a linear, branched or cyclic alkyl group with 1 to 15 C atoms, preferably with 1 to 5 C atoms and particularly preferably with 1 C atom, wherein two or three of the R groups can also be 5 , R 6 and R 7 form a mono-, bi- or tricyclic group. 25 9. Compound according to one or more of claims 1 to 8, selected from the combinations of formulas (IIa1) to (IId1) 30 Formula (IIa1) Formula (IIb1) Foreignfiling_text P24-256.docx -214 - 5 10 Formula (IIc1) Formula (IId1) wherein the symbols have the meanings mentioned in claim 1. 15 10. Combination of formula (IIIa) and (IIIlb), Formula (IIIa) 20 R \ X MM / - R " R 2 25 2 Formula (IIIb) wherein the symbols have the meanings mentioned in claim 1, at least one of the residues R 1 , R 2 and R 3 in formula (IIIa) and at least one of the residues R 1 and R 2 in formula (IIIb) stands for a 30 group of formula (1a) and the dashed line represents any group of connections.

11. Oligomer, polymer or dendrimer containing one or more compounds according to any one of claims 1 to 10, wherein instead of a hydrogen atom or a substituent, one or more bonds of the compounds to the polymer, oligomer or dendrimer are present. Foreignfiling_text P24-256.docx -215 - 12. Formulation or composition comprising at least one compound according to one or more of claims 1 to 10 or an oligomer, polymer or dendrimer according to claim 11 and 5 at least one further compound, wherein the further compound is selected from one or more solvents and / or from the group consisting of fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF, host materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, electron blocking materials and hole blocking materials.

13. Method for producing a compound according to one or more of claims 1 to 10, characterized in that first an aryl halide is reacted to form an aryl metal compound and the aryl metal compound is then reacted with a halogen-silicon compound or a halogen-germanium compound by salt metathesis. 20 14. Use of a compound according to one or more of claims 1 to 10 or of an oligomer, polymer or dendrimer according to claim 11 in an electronic device.

15. Electronic device comprising at least one compound 25 according to one or more of claims 1 to 10 or an oligomer, Polymer or dendrimer according to claim 11. 30 35

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