Use of silicon compounds in an electronic device

Abstract

The present invention relates to the use of organic light-emitting materials, in particular silicon compounds, in electronic devices, in particular in organic electroluminescent devices, as well as to electronic devices, in particular organic electroluminescent devices, containing these OLED materials.

Description

[0001] Foreignfiling_text P24-203.docx

[0002] - 1 -

[0003] Use of silicon compounds in an electronic device

[0004] The present invention relates to the use of organic light-emitting materials, in particular silicon compounds, in electronic devices, in particular in organic electroluminescent devices, 5 and electronic devices, in particular organic electroluminescent devices, containing these OLED materials.

[0005] Electroluminescent devices typically include, in addition to an emission layer, other layers such as one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, and / or charge-generation layers. These layers have a significant influence on the performance of electroluminescent devices.

[0006] 15

[0007] In general, there is still room for improvement in the materials used, especially with regard to efficiency, but also with regard to the lifespan of the device.

[0008] 20 The object of the present invention is therefore to provide compounds which are suitable for use in an organic electronic device, in particular in an organic electroluminescence device, and which, when used in this device, lead to good device properties, as well as to provide the corresponding

[0009] 25 electronic devices.

[0010] In particular, the object of the present invention is to provide compounds that lead to good efficiency and a long lifetime. Besides 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, hereinafter also referred to as host materials, have a significant influence on the lifetime and efficiency of the organic electroluminescence device.

[0011] 35 Foreignfiling_text P24-203.docx

[0012] -2 -

[0013] Furthermore, it is an object of the present invention to provide compounds which are characterized by a low refractive index (RI).

[0014] Another task can be seen as providing electronic devices 5 with excellent performance as cost-effectively as possible and in consistent quality.

[0015] Furthermore, the electronic devices should be usable or adaptable for many purposes. In particular, the performance of the 10 electronic devices should be maintained over a wide temperature range.

[0016] 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, efficiency, and refractive index. The use of these compounds, as well as electronic devices, especially organic electroluminescent devices, containing such compounds, are therefore the subject of the present invention.

[0017] The present invention relates to a use of a compound according to formula (I),

[0018] 25

[0019]

[0020] 30 Formula (I)

[0021] where the following applies to the symbols:

[0022] R aIn each occurrence, the group is a straight-chain alkyl35 group with 1 to 40 carbon atoms, preferably 1 to 20 carbon atoms, either the same or different. Foreignfiling_text P24-203.docx

[0023] - 3 -

[0024] branched or cyclic alkyl group with 3 to 40 carbon atoms, preferably 3 to 20 carbon atoms, or an alkenyl group with 2 to 40 carbon atoms, preferably 2 to 20 carbon atoms, wherein these groups may each be substituted with F, D or a crosslinkable group, preferably D or a crosslinkable group, particularly preferably D; 5 wherein two R groups may be a form a ring together;

[0025] R b In each instance, R represents the same or different values. a , Si(R a )3 or OSi(R a )3; where two remainders R can be b or a remainder R b with a remainder R a form a ring;

[0026] 10

[0027] R cIn each instance, R represents the same or different values. a , Si(R a )3, OSi(R a )3, OR a , (Si(R b )2) s (R b ), O(Si(R b )2) s (R b ), (OSi(R b )2) s (R b ), (C(R d )2) r (Si(R b )2) s (R b ), (Si(R b )2) s (C(R d )2) r (Si(R b )2) s (R b ), (C(R d )2) r O(Si(R b )2) s (R b ) or (Si(R b )2) r O(Si(R b )2) s (R b ); where two 15 remainders R can be used c or a remainder R c with a remainder R a or R b form a ring;

[0028] R d In each instance, it stands for H, D, F, R, either the same or different. a , Si(R a )3 or OSi(R a )3, preferably for H, D, Ra , Si(R a )3 or OSi(R a )3; where two remainders R can be d or a remainder R d with a remainder R a or R b form a 20-ring;

[0029] r is an integer in the range of 1 to 20, preferably 1 to 10, particularly preferably 1, 2 or 3;

[0030] 25 s is an integer in the range of 1 to 20, preferably 1 to 10,

[0031] especially preferred 1, 2 or 3;

[0032] t is an integer in the range of 1 to 20, preferably 1 to 10, particularly preferably 1 to 7;

[0033] 30

[0034] in an electronic device.

[0035] Preferably, the compound according to formula (I) can be used in an electroluminescent device, in particular an organic electroluminescent device.

[0036] Particularly preferred is the use of the compound according to formula (I) in an electronic device for varying the refractive index.

[0037] 5 Two remainders R c at a group Si(R c )2 in formula (I) can be the same or different, preferably in at least one group (Si(R) c )2)t the two remainders R c are different. Furthermore, it may be provided that in at least one group (Si(R) c )2)t the two remainders R c are equal. Preferably, in at least one group, (Si(R) corresponds to (Si(R) c )2)t at least one of the residues R c 10

[0038] a group R a , Si(R a )3 or OSi(R a )3.

[0039] In a preferred embodiment, the compound to be used according to the invention corresponds to the following formula (II),

[0040] 15

[0041]

[0042] Formula (II)

[0043] 20

[0044] where the symbols t, R a , R b and R c the meanings mentioned above, especially for formula (I).

[0045] Formulas (I) and (II) comprise a substructure of the formula (Si(R) c )2)t or 25

[0046] (Si(R c R b ))t. For t greater than 1, this substructure of the formula (Si(R) c )2)t or

[0047] (Si(R c R b ))t may be linear or branched. Preferably, the substructure of the formula (Si(R) may be provided to be (Si(R)). c )2)t or (Si(R c R b ))t is linear. A ring formation within a group of the formula (Si(R) c )2)t or (Si(R c R b ))t or between different groups of the formula (Si(R) c )2)t or (Si(R c R b ))t or a part30

[0048] structure of the formula (Si(R) a )3) with a group of the formula (Si(R c )2) t or

[0049] (Si(R c R b ))t can also be linear in the case of a substructure of the formula (Si(R) c )2)t or (Si(R c R b ))t may be given, as exemplified by connections B39 or B41, which are explained in more detail in the example section. Foreignfiling_text P24-203.docx

[0050] - 5 -

[0051] The rest R c can the groups O(Si(R) b )2) s (R b ), (OSi(R b )2) s (R b ), (C(R d )2) r (Si(R b )2) s (R b ), (Si(R b )2) s (C(R d )2) r (Si(R b )2) s (R b ), (C(R d )2) r O(Si(R b )2) s (R b ), (Si(R b )2) r O(Si(R b)2) s (R b ) include the substructures, such as (Si(R). b )2) s or (C(R) d )2) r These structures can be linear or branched for r or s greater than or equal to 2. Preferably, the substructures can be configured as in example 5 (Si(R). b )2) s or (C(R) d )2) r are linear, as explained in more detail above.

[0052] In a preferred embodiment, R a selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl or tetradecyl, preferably methyl, ethyl, iso-propyl, tert-butyl, neo-pentyl, cyclopentyl, methylcyclopentyl, 10-cyclohexyl, methylcyclohexyl, norbornyl, adamantyl or diamantyl, wherein these groups may be deuterated.

[0053] In a still preferred embodiment, it may be provided that at least two of the residues R b and / or R c for Si(R a)3 or (Si(R b )2) s (R a ) stand.

[0054] 15

[0055] Preferred compounds according to formula (I), which can be used according to the invention, have at least 5, preferably at least 7 Si atoms. Preferably, a compound according to formula (I) comprises 5 to 30, particularly preferably 7 to 24 Si atoms.

[0056] 20

[0057] Furthermore, it is preferably provided that the compound according to formula (I), which is preferably usable according to the invention, has at least 12, preferably at least 16 carbon atoms. Preferably, the compound according to formula (I) comprises 12 to 100, more preferably 16 to 50 carbon atoms.

[0058] 25

[0059] A further preferred compound according to formula (I) has at least two, particularly preferably at least three Si atoms, which have at least three covalent bonds to Si atoms.

[0060] 30 In addition, it may preferably be provided that the compound according to formula (I) has at least one, preferably at least two Si atoms, which has at least four covalent bonds to Si atoms.

[0061] Preferably, a compound according to formula (I) comprises at least two, 35 preferably at least three and particularly preferably at least four. Foreignfiling_text P24-203.docx

[0062] -6 -

[0063] Groups of the formula Si(R a )3, where the remainder R a stands for ethyl, CD2CD3, methyl or CD3, preferably methyl or CD3.

[0064] Two remainders R a , R b or R c can form a ring together. This ring formation can preferably occur, among other things, by the fact that the residues 5 R a , R b or R cThe hydrogen atoms bonded to the silicon atoms are formally cleaved off, so that the two silicon atoms form a covalent bond. Furthermore, a hydrogen atom, for example attached to an alkyl group such as this one for R, can also be formally removed. a is defined, is bound, and can be cleaved off by forming a ring.

[0065] 10 If two or more remainders, which may in particular be selected from R a , R b or R c, forming a ring together, or ring formation in which two Si atoms are covalently bonded to each other occurs through formal elimination of the aforementioned residues, as previously explained, the resulting ring can be monocyclic or polycyclic. The residues forming a ring system can be adjacent, i.e., bonded to the same silicon atom or to silicon atoms directly bonded to each other, or they can be further apart. In the case where two Si atoms are formed by formal elimination of two residues R a , R b or R c For the Si atoms to be covalently bonded to each other, they are preferably not adjacent.

[0066] 20

[0067] In a further embodiment, it can be provided that the compound according to formula (I) has at least one ring with at least 4, preferably at least 5 Si atoms in the ring.

[0068] 25 The compound usable according to the invention according to formula (I) can have crosslinkable groups. Preferably, a crosslinkable group is selected from a terminal or cyclic alkenyl or terminal dienyl or alkynyl group, preferably having 2 to 20, more preferably 2 to 10 carbon atoms; an alkenyloxy, dienyloxy or alkynyloxy group, preferably 30 an alkenyloxy group, preferably having 2 to 20, more preferably 2 to 10 carbon atoms; an acrylic acid group, preferably having 4 to 20, more preferably 4 to 10 carbon atoms; an oxetane or oxirane group, preferably having 2 to 20, more preferably 2 to 10 carbon atoms; a silane group; a cyclobutane group, wherein terminal alkenyl groups are preferred.

[0069] -7 -

[0070] The crosslinkable group can act as a substituent of the group R ain a compound according to formula (I) and / or formula (II). Furthermore, alkenyl groups with 2 to 40 carbon atoms, preferably 2 to 20 carbon atoms, represent crosslinkable groups.

[0071] 5

[0072] Compounds according to formula (I) and / or formula (II) with crosslinkable groups can be used in particular for the production of an outcoupling layer, a capping layer or an matching layer.

[0073] 10

[0074] For other applications, such as in material mixtures used as premix systems, the compounds according to formula (I) and / or formula (II) preferably do not include crosslinkable groups or alkenyl groups with 2 to 40 carbon atoms.

[0075] 15

[0076] Crosslinkable groups are hereinafter sometimes referred to as crosslinkable groups Q. A crosslinkable group Q, as used in the present invention, is a functional group capable of undergoing a reaction 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 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 of an initiator."Insoluble" within the meaning of the present invention preferably means that, after the crosslinking reaction (i.e., after the reaction of the crosslinkable groups), the compound according to the invention 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.

[0077] - 8 -

[0078] 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.

[0079] 5

[0080] According to the invention, the preferred networkable groups Q are the groups listed below:

[0081] a) Terminal or cyclic alkenyl or terminal dienyl and

[0082] 10

[0083] Alkynyl groups:

[0084] Suitable units are those containing a terminal or cyclic double bond, a terminal dienyl group or a terminal triple bond, in particular terminal or cyclic alkenyl, terminal dienyl or terminal alkynyl groups with 2 to 40 carbon atoms, preferably 15

[0085] The group consists of 2 to 10 carbon atoms, whereby individual CH2 groups and / or individual H atoms can also be replaced by the aforementioned R groups. Furthermore, groups that can be considered precursors and that are capable of forming a double or triple bond in situ are also suitable.

[0086] 20

[0087] b) Alkenyloxy, dienyloxy or alkynyloxy groups:

[0088] Alkenyloxy, dienyloxy or alkynyloxy groups are also suitable, preferably alkenyloxy groups.

[0089] 25

[0090] c) Acrylic acid groups:

[0091] Acrylic acid units in the broadest sense are also suitable, preferably acrylic esters, acrylamides, methacryl esters and methacrylamides. C is particularly preferred. 1-10 -Alkyl acrylate and C 1-10 -Alkyl methacrylate.

[0092] 30

[0093] The crosslinking reaction of the groups mentioned above under a) to c) can proceed via a radical, a cationic, or anionic mechanism, as well as via cycloaddition. It can be advantageous to add a suitable initiator for the crosslinking reaction. Suitable initiators for radical crosslinking include, for example, dibenzoyl peroxide, AIBN, or 35.

[0094] TEMPO. Suitable initiators for cationic networking are, for example, Foreignfiling_text P24-203.docx

[0095] - 9 -

[0096] AlCl3, BF3, triphenylmethyl perchlorate or tropylium hexachloroantimonate.

[0097] Suitable initiators for anionic crosslinking are bases, in particular butyllithium. 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.

[0098] d) Oxetanes and oxiranes:

[0099] Another suitable class of crosslinkable groups Q are oxetanes and 10 oxiranes, which crosslink cationically via ring opening. It may be advantageous to add a suitable initiator for the crosslinking reaction.

[0100] Suitable initiators include, for example, AICI3, BF3, triphenylmethyl perchlorate, or tropylium hexachloroantimonate. Photoacids can also be added as initiators.

[0101] 15

[0102] e) Silanes:

[0103] Silane groups SiR3 are also suitable as a class of crosslinkable groups, where at least two R groups, preferably all three R groups, represent Cl or an alkoxy group with 1 to 20 C atoms. This group reacts in the presence of water to form an oligo- or polysiloxane.

[0104] f) Cyclobutane groups

[0105] The crosslinkable groups Q mentioned above under a) to f) are generally known to the person skilled in the art 25, as are the suitable reaction conditions used to react these groups.

[0106] Preferred crosslinkable groups Q include alkenyl groups of the following formula Q1, dienyl groups of the following formula Q2, alkynyl groups of the

[0107] 30 of the following formula Q3, alkenyloxy groups of the following formula Q4, dienyloxy groups of the following formula 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 and Q10, oxirane groups of the following formula Q11, cyclobutane groups of the following formulas Q12, Q13 and Q14:

[0108] 35 Foreignfiling_text P24-203.docx

[0109] - 10 -

[0110] R 1 ! R 1 !

[0111] \

[0112] VR 12 R 12 -(CH2) m^ --(CH2) m A^^

[0113] Q1 Q2

[0114] 5 R\

[0115] R 11 R 12

[0116] — -fCH2) m — 0 — (CH2) n

[0117] Q3 Q4

[0118] R 11

[0119] 10 ^R 12 „11

[0120] -(CH2) m — O-(CH2) n ^ / — (CH2) m — O — (CH2) n /

[0121] Q5 Q6

[0122] 0 11 VJ ° ° 11

[0123] 15 II R

[0124] '(CH2) A 1 12 1 1

[0125] X O --(CH2) / / \ w A^R

[0126] OT

[0127] R 13 R 1 too \ 3

[0128] Q7 Q8 3

[0129] 20

[0130] from z from z

[0131] Q9 Q10

[0132] 0

[0133] CH 2X

[0134] , C H 2

[0135] 25 ^(CH2) n ^ ^R 11

[0136] Q11 Q12

[0137] r 11 / R 12 13

[0138] V R

[0139] 30 V" R 14

[0140]

[0141] Q13 Q14

[0142] 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 to 4 carbon atoms, occurs in each instance, whether identical or different. Foreignfiling_text P24-203.docx

[0143] - 11 -

[0144] The R are particularly preferred 11 , R 12 , R 13 and R 14H, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, sec-Butyl or tert-Butyl, and especially preferably H or Methyl. The indices used have the following meanings: m = 0 to 8; and n = 1 to 8.

[0145] 5 Ar 10In formula Q14, each occurrence is either the same or different: an aromatic ring system with 6 to 60 aromatic ring atoms, or a heteroaromatic ring system with 5 to 60 aromatic ring atoms, which includes 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 system may be substituted with one or more R' substituents other than H;wherein R' is selected in each occurrence, either the same or different, from the group consisting of H, D, F, an aliphatic hydrocarbon residue with 1 to 20 C atoms, an aromatic ring system with 6 to 30 aromatic ring atoms, or a heteroaromatic ring system with 5 to 30 aromatic ring atoms, in which at least one heteroatom is selected from O and S, preferably a heteroatom selected from O and S, particularly preferably an O atom, wherein in the aromatic and heteroaromatic ring system one or more H atoms may be replaced by D, F and which may be substituted by one or more alkyl groups with 1 to 4 carbon atoms each, wherein two or more substituents R' may form a ring system together;

[0146] The dashed bond in formulas Q1 to Q11 and Q14, as well as the dashed bonds in formulas Q12 and Q13, represent the attachment of the crosslinkable group to the repeating units or a Si atom, as shown in formula (I) and formula (II), respectively.

[0147] The crosslinkable groups of formulas Q1 to Q14 can be directly linked to 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:

[0148] R 11 R 11

[0149] # - 35 R12 / - R12

[0150] - (CH2) m Ar 10 ^— '

[0151]

[0152] - Ar 10 — (CH2) m - Foreignfiling_text P24-203.docx

[0153] 5

[0154] 10

[0155] 15

[0156] 20

[0157] 25

[0158]

[0159] 30

[0160] where Ar 10 in formulas Q15 to Q28 the meaning previously explained, especially for formula Q14.

[0161] The following groups are particularly preferred for networking: 35 Foreignfiling_text P24-203.docx

[0162] - 13 -

[0163] HH

[0164] H > H -(CH2) m ^ -(CH2) m ^^

[0165] Q1a Q2a

[0166] 5 0

[0167] JSy & R 11

[0168] OIM \

[0169] H o R □

[0170] -(CH2) m — O-(CH2) n ^ H

[0171] . (CH2) m

[0172] 10

[0173] Q4a Q7a

[0174] 0

[0175] H

[0176] o^V^H ' '" x o' zZ ^x^

[0177] 15 I I 13

[0178] . (CH2) m

[0179] 0

[0180] r- -7o

[0181] Q7b Q9a co

[0182] CH 2X

[0183] 20, C H 2

[0184] Q12 Q13

[0185] R 11 \ VR 12 25

[0186] Q14a Q15a

[0187] R\

[0188] \ R 12 R11 \ \_ R 12 - (CH^—. (CH2) m — 0— (CH2) n — 30

[0189]

[0190] Q16a Q18a

[0191] 35 Foreignfiling_text P24-203.docx

[0192] "■Q. H R”

[0193] NCH-A Ä J X (CH2) n Ä U \ i

[0194] x o

[0195] 5 H

[0196] Q21a Q21b

[0197] -OL (CH2) n ^o ^^

[0198] t

[0199] 10 o z

[0200] Q23a Q26a

[0201] c. 11 D 12

[0202] V r13 XZ R14

[0203] 15 ( H2C\ o Qj

[0204] \: 'n

[0205]

[0206] Q27a Q28a

[0207] The remains R 11 , R 12 , R 13 and R 14 are with every occurrence, equally or

[0208] 20

[0209] various, 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.

[0210] 25

[0211] The indices used have the following meaning: m = 0 to 8 and n = 1 to 8.

[0212] The following groups are particularly preferred for networking:

[0213] 30

[0214] HH

[0215] H

[0216] — H

[0217] 35

[0218]

[0219] Q1b Q1c Foreignfiling_text P24-203.docx

[0220] - 15 - HH

[0221] H

[0222] 5 Q2b Q2c

[0223] H o HO' \ H,. QX HHH

[0224] 10 Q4b Q7c

[0225] 0

[0226] 0 - \ H CH 2X

[0227] H 3 C >=< H, C H 2

[0228] 15 Q7d Q12a

[0229] HH

[0230] / H

[0231] IH

[0232] O' x — /

[0233] I

[0234] 20 Q13a Q14b

[0235] H

[0236] H

[0237] — H

[0238] 25 Q15b Q15c

[0239] H H

[0240] H

[0241] j H

[0242] 30

[0243] Q15d Q15e

[0244] H

[0245] 35

[0246]

[0247] Q15f Q15g Foreignfiling_text P24-203.docx

[0248] - 16 - H H H H

[0249] Q16b Q16c

[0250] 5 H H

[0251] 10 Q16d Q16e

[0252] / 0

[0253] H U H V - H CH 3

[0254] 15

[0255] Q21c Q21d

[0256] Q26b Q26c

[0257] 20

[0258]

[0259] Q27b Q27c

[0260] 25

[0261] The compounds usable according to the invention preferably contain only the groups described above, so that the compound preferably consists essentially of C, H, D, F, Si and O atoms. Furthermore, the compounds according to formula (I) preferably do not comprise aromatic or hetero30

[0262] aromatic ring systems, as defined above and below. However, the crosslinkable groups shown above and below can include further heteroatoms, for example sulfur atoms, although these heteroatoms are not preferentially contained in the crosslinkable groups. Furthermore, the crosslinkable groups can be aromatic and hetero35

[0263] aromatic ring systems are included, the definition of which is shown below. Foreignfiling_text P24-203.docx

[0264] - 17 -

[0265] The preferred group is crosslinkable groups that do not contain aromatic or heteroaromatic ring systems.

[0266] Within the scope of the present invention, an aliphatic hydrocarbon residue or an alkyl group or an alkenyl or alkynyl group, which may contain 1 to 40 carbon atoms, preferably 1 to 20 carbon atoms, and in which individual hydrogen atoms or CH₂ groups may also be substituted by the aforementioned groups, preferably the residues methyl, 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, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, Ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethinyl, propynyl, butynyl, pentinyl, hexinyl, heptinyl, or octinyl are understood to be alkoxy groups. An alkoxy group with 1 to 40 carbon atoms preferably includes methoxy, trifluoromethoxy, ethoxy,

[0267] 15 n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy,

[0268] s-Pentoxy, 2-Methylbutoxy, n-Hexoxy, Cyclohexyloxy, n-Heptoxy, Cycloheptyloxy, n-Octyloxy, Cyclooctyloxy, 2-Ethylhexyloxy, Pentafluoroethoxy, and 2,2,2-Trifluoroethoxy are understood to be. In general, alkyl or alkoxy 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, preferably D.

[0269] 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 carbon atoms and heteroatoms is at least 5. The heteroatoms are selected from oxygen and / or sulfur. 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. Aromatics linked together by single bonds, such as biphenyl, are not referred to as aryl or heteroaryl groups, but as aromatic ring systems.

[0270] - 18 -

[0271] 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, with the proviso 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, and likewise systems in which two or more aryl groups.

[0272] 15, for example, are connected 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 together by single bonds.

[0273] 20 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 positions on the aromatic or heteroaromatic compound, is understood to include in particular groups derived from benzene, naphthalene, anthracene, 25 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, 30 dibenzothiophene, preferably dibenzofuran and dibenzothiophene, especially preferably dibenzofuran, or groups derived from combinations of these systems.

[0274] The phrase "two or more residues can form a ring 35" is used, among other things, in the present description Foreignfiling_text P24-203.docx

[0275] - 19 -

[0276] It can be understood that the two residues are linked to each other by a chemical bond, formally involving the elimination of two hydrogen atoms. This is illustrated by the following scheme.

[0277] Ring formation

[0278] 5

[0279] the remains R

[0280]

[0281] Furthermore, the above-mentioned wording should also be understood to mean 10

[0282] It is assumed 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 illustrated by the following diagram:

[0283] 15 Ring formation of the residues R

[0284]

[0285]

[0286] 20 Preferably, the compound according to formula (I) may comprise 1 to 10, preferably 1 to 5, crosslinkable groups.

[0287] In a still preferred embodiment, it may be provided that the connection according to formula (I) does not include any networkable groups.

[0288] 25

[0289] In a preferred embodiment, the compounds usable according to the invention have a high degree of deuteration. Preferably, the degree of deuteration can be at least 50%, more preferably at least 80%, more 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 1Hydrogen (D / (D+H)*100). The compounds are particularly preferred if they are fully deuterated.

[0290] The ordinary refractive indices of the 35 compounds according to the invention, measured via ellipsometry at 450 nm, are preferably < 1.7, more preferably < 1.6, particularly preferably < 1.55 and especially preferably < 1.50. Foreignfiling_text P24-203.docx

[0291] -20 -

[0292] 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.

[0293] 5

[0294] Furthermore, preferred compounds according to the invention are characterized by being sublimable or vaporizable. These compounds generally have a molar mass of less than approximately 1500 g / mol.

[0295] 10 Furthermore, it may be provided that the compound according to formula (I) has a sublimation temperature in the range of 50 to 500 °C, preferably 150 to 400 °C, particularly preferably 220 to 380 °C and especially preferably 250 to 350 °C measured according to DIN 51006 (10 -2 mbar vacuum, TGA). Corresponding evaporation temperatures apply for decomposition-free evaporation.

[0296] Furthermore, it can be provided that the compound according to formula (I) is meltable without decomposition above a temperature of 50 °C, preferably above a temperature of 100 °C.

[0297] 20

[0298] 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.

[0299] 25

[0300] 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.

[0301] 30

[0302] Examples of preferred connections according to the embodiments listed above are the connections listed in the following table.

[0303] 35 Foreignfiling_text P24-203.docx

[0304] - 21 -

[0305] 2 2

[0306] , -. > Si Si,, -. \ s — Si- Si- Si — ' \ / \ \ 1 1 / / \

[0307] ( ) — Si Si - Si Si — ( > \ _ / / I 1 \ \ _ /

[0308] . Si.. Si. ' - ' 662

[0309] Ö Ö

[0310] 1 2

[0311] 2 5 2 2

[0312] i - <. < Si Si, - -.

[0313] \ / \ \ Si S 1i SS / i — / r\ \. * l. J / / z Z / / 1 I 1 \

[0314] 2 6 6 6

[0315] 3 4

[0316] 2 2

[0317] . - > > Si Si,, - - r _\ ) — \ Si i 1 i * / / > \ ii / ZA — Si — Si — Si — Si — \ \ — Si Si - Si Si — \ 2 <77 / 1 I 1 \ \ 2? / I 1 \ \ V. Si. 1 . Si.. SL. Si. - '

[0318] 2 2 2 6

[0319] 5 6

[0320] .62 2 f2 2VT cv Z S 'x 1. Z'^i'v

[0321] 7 8

[0322] 3s{SiC

[0323] From 7

[0324] }Si >k

[0325] . 0 S0 zw

[0326]

[0327] 9 10 Foreign filing_text P24-203.docx

[0328] - 22 -

[0329] Z2, A

[0330] r~ Si- Si- Si-Si-Si- S —Si — z

[0331] And 1 And

[0332] 1 1 12

[0333] ^Si x zYes

[0334] You are Z About z / si fz / ;si z / A / About from \ AV / \ / Az Si 7 \ / ;

[0335] You are / z \

[0336] AX Si" >\X

[0337] < T b

[0338] 13 14 A AsiT / T \,sA

[0339] / ^Si z Si^A \ —Si VsiA>

[0340] \ k -Sk x JSi

[0341] \ "; Si / ^Si \ I JJj^ x

[0342] 15 ^ > 16 0 Q i O

[0343] ^ASL / X x — / \ z®'""

[0344] O / o ^ >>p< / s 'vvA 17 18

[0345] Ai 1 / \ IA AL \ / S / iA\\siP v \ \ \ ^si x / . / A" Si— ) / S| —Yes Yes — <3 \ \ A

[0346] — SL. Si — / S' / Si Si— / / / Si \ J \. ' —! \ Si — S I. / ^Si Si — i— Si — / T \ x x about

[0347]

[0348] 19 20

[0349] 35 Foreignfiling_text P24-203.docx

[0350] 5

[0351] 10

[0352] 15

[0353] 20

[0354] 25 30

[0355]

[0356] 35 Foreignfiling_text P24-203.docx

[0357] / \.\?^ / / AA 1 21 1 o 1 1 1 1 A\ — S HS HS i-S HS i — S HS HS HS HS i — < >— S i— Si— S i— S — Si— 1 Si— SHf > w 1 | I l l i i Vj -si- -si- 5 QO

[0358] 31 o 0 32 ö

[0359] o o

[0360] i / \ 7

[0361] -SHSi^JJ / ( SHSHSi^_

[0362] 10 -SA — 1

[0363] 33 34

[0364] 15

[0365] / \ / \ / \ / \ \

[0366] X X < / -■ —

[0367] \ ' ' / \ 'y ' / ü —> —w — —__

[0368] oo

[0369] 20

[0370] 35 36

[0371] i Si >4^ / ^Si S si — <

[0372] 25 / TS < A^S 1i z S 1i — CI

[0373] CF

[0374]

[0375] 37 38

[0376] 30 Some of the compounds usable according to the invention are commercially available or known from the literature. Furthermore, suitably usable compounds can easily be obtained by appropriate modification and adaptation of methods known from the literature.

[0377] 35 Foreignfiling_text P24-203.docx

[0378] -25 -

[0379] These processes, possibly followed by purification, such as...

[0380] Recrystallization or sublimation allows the compounds usable according to the invention to be obtained in high purity, preferably more than 99% (determined by means of 1 H-NMR, HPLC and / or GC).

[0381] 5 The compounds usable according to the invention can also be mixed with a polymer. It is also possible to covalently incorporate these compounds into a polymer. This is particularly possible with compounds comprising crosslinkable groups, as described above. These can be used as monomers for the production of corresponding oligomers, dendrimers 10, or polymers. The compounds and polymers usable according to the invention can be used as a crosslinked or uncrosslinked layer.

[0382] Furthermore, 15 compounds that can be used according to the invention and that are characterized by a high glass transition temperature are of particular interest.

[0383] In this context, compounds according to formula (I) or according to the previously and subsequently described preferred embodiments 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 particularly preferably at least 150 °C, as determined according to DIN 51005 (version 2005-08).

[0384] For the processing of the compounds usable according to the invention from the liquid phase, for example by spin coating or by printing 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 include, 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, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, α-terpineol, benzothiazole, butylbenzoate, cumene, cyclohexanol, and cyclohexanone. Cyclohexylbenzene, Decalin, Dodecylbenzene, Ethyl- Foreignfiling_text P24-203.docx.

[0385] -26 -

[0386] benzoate, indane, NMP, p-cymene, phenetol, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropyl naphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-5-dimethylphenyl)ethane, 2-methylbiphenyl, 3-methylbiphenyl, 1-methylnaphthalene, 1-ethylnaphthalene, ethyl octanoate, diethyl sebacic acid ester, octyl octanoate, heptylbenzene, menthyl isovalerate, cyclohexylhexanoate or mixtures of these solvents.

[0387] 10 Another object of the present invention is therefore a formulation or a composition containing at least one compound according to formula (I),

[0388] R c

[0389] 15

[0390]

[0391] Formula (I)

[0392] 20 wherein the symbols have the aforementioned meanings, and 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 25 of these solvents. If the further compound 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 transport material, a 30 emitting compound 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.

[0393] 35 Foreignfiling_text P24-203.docx

[0394] -27 -

[0395] Another object of the present invention is therefore a composition containing at least one compound according to formula (I),

[0396] R c

[0397] 5

[0398]

[0399] Formula (I)

[0400] the symbols have the aforementioned meanings, and

[0401] 10

[0402] 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 electron15

[0403] Injection materials, electron transport materials, hole injection materials or hole transport materials, particularly preferably electron transport materials or hole transport materials.

[0404] Particularly preferred compounds according to formula (I), which are described in the invention20

[0405] The formulations or compositions that may be included shall correspond to formula (II), with the aforementioned preferences applying accordingly.

[0406] The compounds according to the invention can in particular be used for 25

[0407] to vary the refractive index of functional layers in an electronic device, preferably an electroluminescent device, as described in more detail below. This makes it very easy to adapt and match the refractive indices of different functional layers, thereby preventing an unexpected increase in the 30

[0408] The efficiency of these devices becomes possible.

[0409] In many cases, the aim is to reduce the refractive index of the layers, so that the compounds according to the invention comprise at least one branched alkyl structure, since these generally lead to lower refractive indices than 35

[0410] linear structures. Accordingly, connections usable according to the invention are Foreignfiling_text P24-203.docx

[0411] -28 -

[0412] conditions of the above formula (I) or preferred embodiments thereof, wherein at least one of the residues R a preferably represents a neo-alkyl or t-butyl group.

[0413] The ordinary refractive indices of 5 compositions and / or formulations of the present invention, measured via ellipsometry at 620 nm, are preferably less than 1.75, more preferably less than 1.70, more preferably less than 1.68 and particularly preferably less than 1.66.

[0414] The compound usable 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 has at least two, three, or more components, and finding a power maximum is therefore complex, surprising advantages can arise from using the compounds according to the invention in an electron transport layer and / or a hole transport layer.

[0415] It should be noted that the compounds described above and below, 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 definitions of heteroaryl groups and / or heteroaromatic ring systems presented above must be extended to include compounds containing nitrogen, boron, or phosphorus atoms. This is often indicated by the clarification in section 25 that the heteroaromatic ring systems may contain nitrogen atoms.

[0416] Preferably, it may be provided that the proportion of compounds according to formula (I) or preferred embodiments of this formula in a

[0417] 30. Composition 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.%.

[0418] 35 Foreignfiling_text P24-203.docx

[0419] -29 -

[0420] 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.

[0421] Compounds with hole transport properties, also referred to herein as hole conductor materials 5 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 of 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.

[0422] Preferred compounds exhibiting hole injection and / or hole transport15 properties include, for example, triarylamine, benzidine, tetraaryl-para-phenylenediamine, triarylphosphine, phenothiazine, phenoxazine, dihydrophenazine, thianthrene, dibenzo-para-dioxin, phenoxathiin, carbazole, azulene, thiophene, pyrrole and furan derivatives and other O-, S- or N-containing heterocycles with a high-lying HOMO (HOMO = highest occupied molecule20 orbital).

[0423] Compounds exhibiting hole injection and / or hole transport properties are preferably selected from triarylamines, in particular mono-triarylamines and bis-triarylamines, and carbazolamines. A mono-triarylamine is defined as a compound containing a single amine group, wherein three groups selected from aromatic and heteroaromatic ring systems are bonded to the nitrogen atom of the amine group. A bis-triarylamine is defined as 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 defined as a compound containing 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 the nitrogen atom of the 35 Foreignfiling_text P24-203.docx.

[0424] - 30 -

[0425] The amine group consists of three groups, selected from aromatic and heteroaromatic ring systems.

[0426] In a preferred embodiment, the composition may include at least one hole transport material selected from compounds of formulas (L-1) and / or (L-2).

[0427] Ar 15 Ar 1 * Ar 15 N— Ar 15 N-Ar 16 — N

[0428] 10 ares 15 Ar 15 Ar 15

[0429]

[0430] _ (L-1) _ _ (L-2) _

[0431] where the following applies to the symbols:

[0432] 15

[0433] Ar 15In 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 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 not equal to H substituted 20

[0434] can;

[0435] Ar 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 H in a non-equal way, and heteroaromatic 25

[0436] Ring systems that can contain N atoms, with 5 to 40 aromatic ring atoms separated by R groups 15 can be substituted with something other than H;

[0437] R 15 is chosen from H, D, F, 30 for each occurrence, whether the same or different.

[0438] C(=O)R 16 , CN, Si(R16 )3, N(R 16 )2, P(=O)(R 16 )2, OR 16 , S(=O)R 16 , 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 35

[0439] heteroaromatic ring systems that can contain N atoms, with Foreignfiling_text P24-203.docx

[0440] - 31 -

[0441] 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 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 -,

[0442] 5 -C=C-, Si(R 16 )2, C=O, C=NR16 , -C(=O)O-, -C(=O)NR 16 -, NR 16 ,

[0443] P(=O)(R 16 ), -O-, -S-, SO or SO2; wherein two or more, preferably adjacent, residues R 15 together form a ring system;

[0444] 10 R 16 is chosen from H, D, F in every occurrence, whether the same or different,

[0445] C(=O)R 17 , CN, Si(R 17 )3, N(R 17 )2, P(=O)(R 17 )2, OR 17 , S(=O)R 17 , 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, 15 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 enclosed by R groups 17 can be substituted with non-H and 20 where one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups can each be replaced by -R 17 C=CR 17 -, -C=C-, Si(R 17 )2, C=O, C=NR 17 , -C(=O)O-, -C(=O)NR 17 -, NR 17 , P(=O)(R 17 ), -O-, -S-, SO or SO2; wherein two or more, preferably adjacent, residues R 16 together form a ring system 25;

[0446] R17 The ring system is selected in each occurrence as the same or different from H, D, F, Cl, 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, whereby two or more, preferably adjacent, residues R 17 together form a ring system.

[0447] 35 Foreignfiling_text P24-203.docx

[0448] - 32 -

[0449] 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, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, benzocarbazole, 5-carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine and triazine, each of the groups with R substituents 15 may be substituted.

[0450] Preferably the groups Ar 15same or different at each occurrence 10 selected from monovalent groups representing combinations of 2 to 4 groups selected 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, benzo15thiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine and triazine, each of the groups with R substituents 15 may be substituted.

[0451] Particularly preferred groups Ar 15are, the same 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, 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, dibenzothiophenyl, carbazolyl, pyridyl, pyrimidyl, and triazinyl, each of the above groups with R substituents 15 may be substituted.

[0452] Preferred Groups Ar 16are, the same or different at each occurrence, 30 selected from divalent groups, which differ 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 35 Foreignfiling_text P24-203.docx

[0453] - 33 -

[0454] and triazine, with each of the groups containing residues R 15 may be substituted.

[0455] Preferably the groups Ar 16the same or different at each occurrence chosen from monovalent groups representing combinations of 2 to 4 groups 5 chosen 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, wherein 10 each of the groups with residues R 15 may be substituted.

[0456] Particularly preferred groups Ar 16are, the same or different at each occurrence, chosen from divalent groups consisting of benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene, in particular 9,9'-15 dimethylfluorene and 9,9'-diphenylfluorene, benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, carbazole, benzofuran, benzothiophene, benzo-condensed dibenzofuranyl and benzo-condensed dibenzothiophenyl, each of the above groups with R groups 15 may be substituted.

[0457] 20

[0458] Preferably R 15 Equal 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 hetero25 aromatic ring systems which may contain N atoms, with 5 to 40 aromatic ring atoms; wherein the aforementioned alkyl and alkoxy groups and the aforementioned aromatic and heteroaromatic ring systems are modulated by R groups 16 can be substituted with something other than H.

[0459] 30 Preferably R 16 Equal or different choices made from H, D, F, CN, Si(R) 17 )3, N(R 17)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 contain N atoms, with 5 to 40 aromatic ring atoms; wherein the aforementioned alkyl and alkoxy groups and Foreignfiling_text P24-203.docx

[0460] -34 -

[0461] the aforementioned aromatic and heteroaromatic ring systems by residues R 17 can be substituted with something other than H.

[0462] 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 5 to 40 aromatic ring atoms, and heteroaromatic ring systems which may have N atoms, with 5 to 40 aromatic ring atoms.

[0463] Particularly preferred executions of the connections of the formula (L-1) correspond to the following formulas

[0464] 10

[0465] (R 15 )5 (R 15 ) ( R15 ) 3

[0466] Ar15 J\_^~y R15)5 of T v (Ari7)n X Ar 15 15

[0467] (R 15 )5KX

[0468] ( (R K, X )4I X lA-.

[0469] (L-1-1) (L-1-2)

[0470] R 15 R 15 Ar 15 R 15 The 15 20 (The 17 )n^

[0471] , r15 > X 75 Ar is \ / / Ar 15 < R YES U

[0472] (L-1-3) (L-1-4)

[0473] R 15 R15 (R 1 5)2 The 15 r>15

[0474] R 15 R 15 ] / R 15 The 15 25 / \ / “^-(The 17 )nN.

[0475] (R I5 )4£

[0476] — — X (R 15 )3( R15 )4^ / V\= / \^

[0477] R15^ R 1 5 X ' — \R 15 )3 AR15

[0478] (R 15 )2

[0479] (L-1-5) (L-1-6)

[0480] 30 rOp(R i5 )4

[0481] R 15 yK / Ar \^Ar” XX Ar15 / — < - Y '->-^< Ar17 >n R15 ir < Ari7)n X

[0482] (R >3 Ar 15 (R 15 )4A == / \==X ( R15 )3 35

[0483]

[0484] _ (L-1-7) _ _ (L-1-8) _ Foreignfiling_text P24-203.docx

[0485] 5

[0486]

[0487] where the symbols Ar 15 and R 15 , which have the meanings previously mentioned especially for formula (L-1) and for the other symbols:

[0488] 10

[0489] Ar17 is selected from aromatic ring systems with 6 to 13 aromatic ring atoms, separated by R groups 15 which may be substituted with non-H atoms, and heteroaromatic ring systems which may contain N atoms, with 5 to 13 aromatic ring atoms separated by R groups 15 may be substituted with H15;

[0490] X is chosen from a bond, O, S, NR, in each occurrence, whether the same or different. 15 and (C(R) 15 )2;

[0491] 20 Y 1 is chosen from O or S;

[0492] n is 0 or 1, where n = 0 means that the group with index n does not exist and that the groups bound to the group with index n are directly connected to each other, with the 25 proviso that n is not 0 in the case of formula (L-1-9).

[0493] The preferred group is Ar 17selected from divalent groups derived from benzene, biphenyl, naphthalene, fluorene, in particular 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, each of the groups with R substituents 15 It can be substituted 30.

[0494] 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 an embodiment of formula (L-1-2) are especially preferred: Foreignfiling_text P24-203.docx

[0495] 5

[0496]

[0497] where the symbols and indices have the meaning set out above and 10

[0498] preferably correspond to the preferred embodiments mentioned above.

[0499] Particularly preferred embodiments of the compounds of formula (L-2) correspond to the following formulas (L-2-1) and / or (L-2-2)

[0500] 15

[0501] 20

[0502] 25

[0503]

[0504] where the symbols Ar 15 and R 15 , which have the aforementioned meanings 30

[0505] and preferably correspond to the preferred embodiments mentioned above, and the following applies to the other symbols:

[0506] Y 2 is chosen from a bond, O, S, NR, in every occurrence, whether the same or different. 15 and (C(R) 15 )2; Foreignfiling_text P24-203.docx

[0507] - 37 -

[0508] k is 1, 2, 3 or 4, preferably 1 or 2;

[0509] i is 1, 2 or 3, preferably 1 or 2, particularly preferably 1.

[0510] 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:

[0511] 10

[0512] 15

[0513] 20

[0514] 25

[0515] 30

[0516]

[0517] Foreignfiling_text P24-203.docx

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[0520]

[0521] 35 Foreignfiling_text P24-203.docx

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[0528] 30

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[0932]

[0933] Preferably, these arylamines and heterocycles, which are generally used as 30 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.

[0934] According to a preferred embodiment of the present invention, 35 contains the composition (hereinafter also referred to as the mixture) in addition to the Foreignfiling_text P24-203.docx

[0935] - 81 -

[0936] The components of the compound according to formula (I) and the hole transport material, as previously or preferably described, contain no further components, i.e., functional materials. These are therefore material mixtures that are 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 large number of material sources.

[0937] 10

[0938] Preferred are premix systems consisting of two materials, namely a compound of formula (I) and a compound of formulas (L-1) or (L-2), particularly preferably a compound of formula (I) and a compound 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) or (L-151-9).

[0939] 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), wherein the hole transport material and the compound according to formula (I) are sublimable or evaporable and the difference in the sublimation temperature or evaporation temperature is at most 20 °C, preferably at most 10 °C, particularly preferably 5 °C and particularly preferably at most 2 °C, wherein the sublimation temperature or evaporation temperature is determined by means of vacuum TGA measurement.

[0940] 25

[0941] This design provides easily and safely sublimable compositions that can be used particularly reliably in a plant for the production of very high-quality electronic devices.

[0942] 30 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.

[0943] Compounds exhibiting electron injection and / or electron transport properties, hereafter referred to as electron transport materials, 35 include, for example, pyridine, pyrimidine, pyridazine, pyrazine, oxadiazole, Foreignfiling_text P24-203.docx

[0944] - 82 -

[0945] Quinoline, quinoxaline, anthracene, benzanthracene, pyrene, perylene, benzimidazole, triazine, ketone, phosphine oxide and phenazine derivatives, but also triarylboranes and other O-, S- or N-containing heterocycles with a low-lying LUMO (LUMO = lowest unoccupied molecular orbital).

[0946] 5 Particularly suitable compounds for electron-transporting and electron-injecting layers are metal chelates of 8-hydroxyquinoline (e.g., LiQ, AlQ3, GaCh, MgCh, ZnCh, InCh, ZrC), BAIQ, Ga-oxinoid complexes, 4-azaphenanthrene-5-ol-Be complexes (US 5529853 A, see formula ET-1), butadiene derivatives (US 4356429), heterocyclic optical brighteners (US 4539507), 10 benzimidazole derivatives (US 2007 / 0273272 A1), such as TPBI (US 5766779, see formula ET-1).

[0947] Formula ET-2), 1,3,5-triazines, e.g. B. 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 2003-115387, JP 2004-311184, JP-2001-267080, WO

[0948] 15 2002 / 043449), sila-cyclopentadiene derivatives (EP 1480280, EP 1478032, EP 1469533), borane derivatives such as triarylborane derivatives with Si (US 2007 / 0087219 A1, see formula ET-3), pyridine derivatives (JP 2004-200162), phenanthrolines, especially 1,10-phenanthroline derivatives, such as... B. BCP and Bphen, also several phenanthrolines linked via biphenyl or other aromatic groups (US- 20 2007-0252517 A1) or phenanthrolines linked with anthracene (US 2007- 0122656 A1, see formulas ET-4 and ET-5).

[0949] 25

[0950]

[0951] 30

[0952] TPBI

[0953] 2,2',2"-(1,3,5-benzenetriyl)tris(1-phenyl-1 H-benzimidazole Formula ET-1 Formula ET-2

[0954] 35 Foreignfiling_text P24-203.docx

[0955] 5

[0956] Formula ET-4

[0957]

[0958] 10

[0959]

[0960] Heterocyclic organic compounds, such as thiopyran dioxides, oxazoles, triazoles, imidazoles, or oxadiazoles, are also suitable. Examples of the use of five-membered rings with N include oxazoles, preferably 1,3,4-oxa-15.

[0961] diazoles, which are set out, among others, in US 2007 / 0273272 A1; thiazoles, oxadiazoles, thiadiazoles, triazoles, etc., see US 2008 / 0102311 A1 and YA Levin, MS Skorobogatova, Khimiya Geterotsiklicheskikh Soedinenii 1967 (2), 339-341. Silacyclopentadiene derivatives. Also organic compounds such as derivatives of fluorenone, fluorenylidenemethane, perylenetetracarbonic acid, 20

[0962] Anthraquinone dimethane, diphenoquinone, anthrone and anthraquinone diethylenediamine can be used.

[0963] Preferably, 2,9,10-substituted anthracenes (with 1- or 2-naphthyl and 4- or 3-biphenyl) or molecules containing two anthracene units are used.

[0964] 25

[0965] (US 2008 / 0193796 A1, see formula ET-6). The combination of 9,10-substituted anthracene units with benzimidazole derivatives is also very advantageous (US 2006147747 A and EP 1551206 A1, see formulas ET-7 and ET-8).

[0966] 30

[0967]

[0968] 35

[0969]

[0970] Foreignfiling_text P24-203.docx

[0971] -84 -

[0972]

[0973] 5 Formula ET-8

[0974] In a preferred embodiment, the composition may include at least one electron transport material selected from compounds of formulas (E-1) to (E-4).

[0975] 10

[0976] R 15 x_ / N \^ Ar18 JSL

[0977] H 1 ll '-J-Ar 18

[0978] N N.

[0979] \^ N

[0980] (R 15 )3

[0981] R 15

[0982] 15 (E-1) (E-2)

[0983] , N.

[0984] |f ^Ar 18

[0985] l4 - 1 1

[0986] ^\R 15 )4

[0987]

[0988] _ (E-3) _ _ (E^) _

[0989] 20

[0990] where the symbol R 15 , which has the meaning previously mentioned especially for formula (L-1) and which applies to the further symbol:

[0991] Ar 18 is selected from aromatic ring systems with 6 to 50 aromatic ring atoms, separated by R groups 15 can be substituted with non-H, 25 and heteroaromatic ring systems which can have N atoms, with 5 to 50 aromatic ring atoms separated by R groups 15 can be substituted with something other than H.

[0992] Compounds according to formulas (E-1) to (E-3) are preferred.

[0993] 30

[0994] 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)

[0995] 35 Foreignfiling_text P24-203.docx

[0996] 5

[0997] 10

[0998]

[0999] where the symbols R 15, which has the meaning previously mentioned in particular for formula (L-1) and preferably the preferred one mentioned above

[1000] 15 embodiments correspond and the following applies to the other symbols:

[1001] Ar 19 is selected from aromatic ring systems with 6 to 20 aromatic ring atoms, separated by R groups 15 which may be substituted with non-H atoms, and heteroaromatic ring systems which may contain N atoms, 20 with 5 to 20 aromatic ring atoms, which are separated by R groups 15 can be substituted with something other than H;

[1002] m is 0 or 1, where m = 0 means that the group with index m does not exist and that the values ​​attached to the group (Ar 19 ) m The 25 bound groups are directly connected to each other.

[1003] Preferred specific compounds that can be used as electron transport materials according to the present invention are listed in the following table:

[1004] 30

[1005] 35

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[1080]

[1081] with cn

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[1093]

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[1106] - 91 -

[1107] 5

[1108] 10

[1109]

[1110] 15

[1111] 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 electron transport material as previously or preferably described, no further components, i.e., functional materials. These are therefore material mixtures that are used as such for the fabrication of the electron transport layer. These mixtures are also referred to as premix systems, which are used as the sole material source in the deposition of the materials for the electron transport layer and which provide a constant

[1112] The mixing ratio during evaporation is 25. This allows for the simple and rapid deposition of a layer with a uniform distribution of components, without the need for precise control of numerous material sources.

[1113] 30 Preferably, premix systems consisting of two materials are preferred, namely a compound of formula (I) and a compound of formulas (E-1), (E-2), (E-3) or (E-4), particularly preferably a compound of formula (I) and a compound of formulas (E-1-1) or (E-1-2).

[1114] 35 Foreignfiling_text P24-203.docx

[1115] - 92 -

[1116] Preferably, the composition may further include 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 or evaporable and the difference in the sublimation temperature or evaporation temperature is at most 5–20 °C, preferably at most 10 °C, particularly preferably 5 °C and particularly preferably at most 2 °C, wherein the sublimation temperature or evaporation temperature is determined by vacuum TGA measurement.

[1117] This design provides easily and safely sublimable compounds that can be used particularly reliably in a plant for the production of very high-quality electronic devices.

[1118] 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 (relative to vacuum level), and particularly preferably less than -2.7 eV, as defined by quantum mechanical calculations.

[1119] Furthermore, the compositions according to the invention can comprise at least one hole-blocking material (HBM). A hole-blocking material is a material which, in a multilayer composite, prevents or minimizes the transmission of holes (positive charges), particularly if this material is arranged in the form of a layer adjacent to an emission layer or a hole-conducting layer. In general, a hole-blocking material has a lower HOMO level than the hole-conducting material in the adjacent layer. Hole-blocking layers are frequently arranged between the light-emitting layer and the electron transport layer in OLEDs.

[1120] 30 In principle, any known hole-blocking material can be used.

[1121] In addition to other hole-blocking materials described elsewhere in this application, suitable hole-blocking materials include metal complexes (US 2003 / 0068528), such as bis(2-methyl-8-quinolinolato)(4-phenylphenolato)-aluminium(III) (BAIQ). Fac-tris(1-phenyl-35-pyrazolato-N,C2)iridium(III) (Ir(ppz)3) is also used for these purposes.

[1122] - 93 -

[1123] (US 2003 / 0175553 A1). Phenanthroline derivatives, such as BCP, or phthalimides, such as TMPP, can also be used. Furthermore, suitable hole-blocking materials are described in WO 00 / 70655 A2, WO 01 / 41512 and WO 01 / 93642 A1.

[1124] 5. 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, particularly if this material is in the form of a layer adjacent to a

[1125] 10. An emission layer or an electron-conducting layer is arranged. In general, an electron-blocking material has a higher LUMO level than the electron-transporting material in the adjacent layer.

[1126] In principle, any known electron-blocking material can be used. In addition to other electron-blocking materials set out elsewhere in the present application, suitable electron-blocking materials include transition metal complexes such as lr(ppz)3(US 2003 / 0175553).

[1127] 20 Preferably the electron blocking material can be selected from amines, triarylamines and their derivatives.

[1128] 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.

[1129] 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 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 performed with the same Foreignfiling_text P24-203.docx

[1130] -94 -

[1131] The method (B3LYP / 6-31G(d)) and the optimized ground-state geometry were calculated. The default settings for SCF and gradient convergence were used. The HOMO and LUMO values ​​in eV, derived from the quantum chemical calculation, were additionally scaled by the following factors:

[1132] 5 HOMO_corr = 0.90603 * HOMO (in eV) – 0.84836

[1133] LUMO_corr = 0.99687 * LUMO (in eV) – 0.72445

[1134] For the purposes of this application, these values ​​are to be regarded as HOMO or LUMO energy levels of the materials.

[1135] 10. The lowest triplet state Ti is defined as the energy of the lowest-energy triplet state resulting from the described quantum chemical calculation. The lowest excited singlet state Si is defined as the energy of the lowest-energy excited singlet state resulting from the described quantum chemical calculation.

[1136] 15

[1137] A further object of the present invention is an electronic device comprising at least one connection according to formula (I),

[1138] R c

[1139] 20

[1140]

[1141] Formula (I)

[1142] 25

[1143] 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 which contains at least one organic compound. The component can be 30

[1144] including inorganic materials or layers that are entirely composed of inorganic materials.

[1145] Particularly preferred compounds according to formula (I), which may be included in the electronic devices according to the invention, correspond to 35

[1146] Formula (II), where the aforementioned preferences apply accordingly. Foreignfiling_text P24-203.docx

[1147] - 95 -

[1148] 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 5 (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 electrical sensors, preferably organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.), particularly preferably organic light-emitting diodes (OLEDs), small-molecule organic light-emitting diodes (sOLEDs), polymer-based organic light-emitting diodes (PLEDs), especially phosphorescent OLEDs.

[1149] 20 The organic electroluminescent device contains a cathode, anode, and at least one emitting layer. In addition to these layers, it may contain 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, 25 electron blocking layers, and / or charge-generation layers. Interlayers, which may, for example, have an exciton-blocking function, may also be introduced between two emitting layers. It should be noted, however, that not every one of these layers is necessarily present. The organic 30 electroluminescent device may contain one emitting layer, or it may contain several emitting layers.If multiple 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, which can fluoresce or phosphoresce, are used in the emitting layers.

[1150] - 96 -

[1151] Preferred are systems with three emitting layers, wherein the three layers exhibit blue, green, and orange or red emission. The organic electroluminescent device according to the invention can also be a tandem electroluminescent device, particularly for white-emitting OLEDs.

[1152] 5

[1153] The compound according to formula (I) or the preferred embodiments described above can be used in different layers, depending on the precise structure. An organic electroluminescent device containing a compound according to formula (I) or the preferred embodiments described above in 10 is preferred in an electron transport layer and / or in a hole-blocking layer. Furthermore, an organic electroluminescent device containing a compound according to formula (I) or the preferred embodiments described above in a hole transport layer and / or electron-blocking layer is preferred. The compound according to formula (I) or the preferred embodiments described above can also be used in an emission layer.

[1154] Emission layers generally comprise emitters. The term emitter 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 with the emission of light. Generally, two classes of emitters are known: fluorescent and phosphorescent emitters. The term fluorescent emitter refers to 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.

[1155] Emitters are often also referred to as dopants if the dopants cause the 30 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. [The following appears to be unrelated and possibly a separate document fragment: "Under the term Foreignfiling_text P24-203.docx"]

[1156] - 97 -

[1157] Phosphorescent emitters can therefore also be understood as phosphorescent dopants, for example.

[1158] Preferably, the fluorescent emitter in the composition has a peak emission wavelength between 420 - 550 nm, preferably between 420 - 470 nm.

[1159] Preferred fluorescent emitting compounds for hyperphosphorescent OLEDs are selected from the class of arylamines. For the purposes of this invention, an arylamine or aromatic amine is understood to be a compound containing three substituted or unsubstituted aromatic or heteroaromatic ring systems directly bonded to the nitrogen atom. 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 include aromatic anthracene amines, aromatic anthracene diamines, aromatic pyrene amines, aromatic pyrenediamines, aromatic chrysene amines, or aromatic chrysenediamines. An aromatic anthracene amine 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 defined as a compound in which two diarylamine groups are directly bonded to an anthracene group, 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 benzo-35 indenofluorenes disclosed in WO 2014 / 111269 and WO 2017 / 036574, and the Foreignfiling_text P24-203.docx.

[1160] - 98 -

[1161] Phenoxazines and the furan- or thiophene-bound fluorine derivatives disclosed in WO 2016 / 150544. Furthermore, boron compounds 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, KR 2018046851, WO 2019 / 009052, WO 5

[1162] 2020 / 101001, US 2020 / 0207787, WO 2020 / 138874, KR 2020081978, JP 2020-147563, US 2020 / 0335705 or KR 2022041028 may be used.

[1163] Preferably, the at least one fluorescent emitter has a full width at half maximum (FWHM) ≤ 50 nm, 10

[1164] preferably FWHM ≤ 40 nm, further preferred FWHM ≤ 30 nm.

[1165] 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 15

[1166] fluorescent emitters have a HOMO of -4.8 eV to -5.2 eV, preferably from -4.9 eV to -5.1 eV, as defined by quantum chemical calculations.

[1167] Preferably, the energy of the lowest singlet state Si of the fluorescent emitter is between 2.65 eV and 2.9 eV, preferably between 2.7 and 2.8 eV, further before20

[1168] zuggt 2.7 to 2.75 eV, as defined by quantum mechanical calculations.

[1169] In a preferred embodiment of the invention, the fluorescent emitter is selected from structures of the following formula (F-1),

[1170] 25

[1171] 30

[1172]

[1173] Formula (F-1)

[1174] where R has the meanings mentioned above and the following applies to the other symbols and indices used:

[1175] 35 Foreignfiling_text P24-203.docx

[1176] - 99 -

[1177] Ar 30 , Ar 31 , Ar 32 is the same or different in each occurrence a substituted or unsubstituted aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, wherein the heteroaromatic ring system may contain nitrogen, boron and / or phosphorus atoms;

[1178] 5 Y 30 is B or N;

[1179] Y 31 , Y 32 , Y 33 is the same or different in each occurrence and stands for O, 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 B represents 10, at least one of the groups Y 31 , Y 32 , Y 33 NR° stands for, and if Y 30 N stands for at least one of the group Y 31 , Y 32 , Y 33 BR° stands for;

[1180] 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 a

[1181] 15 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 Fl atoms may be replaced by D or F, or an aromatic or 20 heteroaromatic ring system with 5 to 40, preferably with 5 to 30,

[1182] 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; wherein two adjacent substituents R° may form an aliphatic or aromatic ring system, which may be substituted with one or more substituents R;

[1183] q is either 0 or 1.

[1184] 30 Connections are particularly preferred where the following applies:

[1185] q = 0; Y 30 = B; and Y 31 , Y 32 = NR°; or

[1186] q = 0; Y 30 = B; and Y 31 , Y 32 = NR°; or

[1187] q = 1; Y 30 = N; and Y 31 , Y 32 = BR°; Y 33 = chemical bond.

[1188] 35 Foreignfiling_text P24-203.docx

[1189] - 100 -

[1190] Examples of suitable fluorescent emitters are shown in the table below: _ _ _

[1191] DD

[1192] w

[1193] 5 a 9t0r?o D D D

[1194] jM 'i

[1195] 10 xtro, dcböö 9 a5tWm

[1196] a / xt\9 15 T soo

[1197] w

[1198] 20 atro XtTCk arn -ö

[1199] 25 OTT T oa 9t2m9 an

[1200] COO

[1201] w O XJ J TT TT

[1202] 30

[1203]

[1204] orrT oot ' 3 atro

[1205] 35 ForeignFiling_Text P24-203.docx

[1206] - 101 -

[1207] 5

[1208] 10

[1209] 15

[1210] 20

[1211] 25

[1212] 30

[1213]

[1214] 35 ForeignFiling_Text P24-203.docx

[1215] - 102 -

[1216] 5

[1217] 10

[1218] 15

[1219] 20

[1220] 25

[1221] 30

[1222] 35

[1223]

[1224] ForeignFiling_Text P24-203.docx

[1225] - 103 - rO Ch

[1226] uU? Q6Ö YOU N ^

[1227] xiAxrA xr 5 8ö 6 6 6Ö 9 9 9 9 Ccxp QuO

[1228] CM? < JhO 10 Q Ö Ö Q Ow XW vO 6 6 6 CM? 9CO ChQ D QLJO 15 aÄ xxÄ oa;xXvh o xr6 ö tr hyy 5 cw 0-0 20 Q N J^ QM O \ N ^ Q / O OLAOCOAX) QÄ XXÄ O 6 6 6 6 6 6 6 25 Oo M

[1229] ov? Q / the CM? Q.-O OK XCÖJO MÄ XXÄ M

[1230] 66 6 6 66 30

[1231] oh hö CM??uo CIÄ XMXO aZtXüXo 35

[1232]

[1233] 6 6 ö ö 0 ö 6 0 Foreignfiling_text P24-203.docx

[1234] - 104 -

[1235] 5

[1236] 10

[1237] 15

[1238] 20

[1239] 25

[1240]

[1241] 30

[1242] 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 via a spin-forbidden transition, e.g., a transition from an excited triplet state or a state with a higher spin quantum number, e.g., Foreignfiling_text P24-203.docx

[1243] - 105 -

[1244] a quintet state. Phosphorescent compounds are preferably luminescent complexes with transition metals or lanthanides, particularly when they contain copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium, especially compounds containing iridium, platinum, or copper. Within the scope of the present invention, all luminescent iridium, platinum, or copper complexes are considered phosphorescent emitting compounds. Iridium or platinum complexes are particularly preferred.

[1245] Examples of phosphorescent emitters can be found in the applications.

[1246] 10 WO 00 / 70655, WO 2001 / 41512, WO 2002 / 02714, WO 2002 / 15645, EP 1191613, EP 1191612, EP 1191614, WO 05 / 033244, WO 05 / 019373, US 2005 / 0258742, WO 2009 / 146770, WO 2010 / 015307, WO 2010 / 031485, WO 2010 / 054731, WO 2010 / 054728, WO 2010 / 086089, WO 2010 / 099852, WO 2010 / 102709, WO 2011 / 032626, WO 2011 / 066898, WO 2011 / 157339, WO 2012 / 007086, WO 15 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, WO 2018 / 041769, WO 2019 / 020538, WO This can be taken from 2018 / 178001, WO 2019 / 115423 and WO 2019 / 158453. In general, all phosphorescent complexes 20 such as are used for phosphorescent OLEDs according to the prior art and as are known to the skilled person in the field of organic electroluminescence are suitable, and the skilled person can use further phosphorescent complexes without inventive effort.Since the compounds used according to the invention can also exhibit a high triplet energy 25 depending on the substitution, it is particularly possible to use them as matrix materials for blue phosphorescent emitters. Suitable phosphorescent metal complexes, which 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 30 et al., Sci. Adv. 2022, 8, 1641. Further compounds suitable as sensitizers are disclosed in EP 3435438 A2, in particular compounds 2 and 3 on page 21; in CN 109111487, in particular the compounds on pages 76 and 77; in US 2020 / 0140471, in particular the compounds on pages 166 to 175; in KR 2020108705, in particular the compounds on pages 8 to 14, 35; in US 2019 / 0119312, in particular the compounds on pages 114 to Foreignfiling_text P24-203.docx.

[1247] - 106 -

[1248] 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.

[1249] 5. In this case, the proportion of matrix material in the emitting layer is between 50.0 and 99.9 vol.%, preferably between 80.0 and 99.5 vol.%, and 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.

[1250] 10

[1251] Accordingly, the proportion of the emitting compound is between 0.1 and 50.0 vol.%, preferably between 0.5 and 20.0 vol.%, 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.

[1252] 15

[1253] 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 the ones with the smaller proportion in the system, and the matrix materials are the ones 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.

[1254] 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 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, more preferably 1:10 to 1:1, and most preferably 1:4 to 1:1. Mixed matrix systems are preferably used in phosphorescent or hyperphosphorescent organic electroluminescent devices. Particularly suitable matrix materials, which in combination with the inventive Foreignfiling_text P24-203.docx

[1255] - 107 -

[1256] Compounds that can be used as matrix components of a mixed matrix system are explained in more detail below.

[1257] Examples of phosphorescent compounds are listed below.

[1258] 5

[1259] 10

[1260] 15

[1261] 20

[1262] 25

[1263] 30

[1264] 35

[1265]

[1266] Foreignfiling_text P24-203.docx

[1267] - 108 -

[1268] 5

[1269] 10

[1270] 15

[1271] 20

[1272] 25

[1273] 30

[1274]

[1275] 35 Foreignfiling_text P24-203.docx

[1276] - 109 -

[1277] 5

[1278] 10

[1279] 15

[1280] 20

[1281] 25

[1282] 30

[1283]

[1284] 35 Foreignfiling_text P24-203.docx

[1285] - 110 -

[1286] 5

[1287] 10

[1288]

[1289] 15 In a preferred embodiment, a hyperfluorescence and / or hyperphosphorescence system is preferably formed by a suitable combination of compounds.

[1290] Preferably, a fluorescent emitter is used in combination with one or more phosphorescent materials (triplet emitter) and / or a compound that represents a TADF (thermally activated delayed fluorescence) host material.

[1291] 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 those skilled in the art know, 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.

[1292] 35 Foreignfiling_text P24-203.docx

[1293] - 111 -

[1294] A fluorescent emitter can preferably be used in combination with a TADF host material and / or a TADF emitter, as previously outlined.

[1295] The process known as thermally activated delayed fluorescence (TADF) is used, for example, by BH.

[1296] Uoyama et al., Nature 2012, Vol. 492, 234, described this process. To enable it, the emitter has a comparatively small singlet-triplet distance ΔE(S1–T1) of, for example, less than about 2000 cm. -1 necessary. In order to open the spin-forbidden transition T1→ S1, a further compound can be provided in the matrix next to the emitter, which has a strong spin-orbit coupling, so that inter-system crossing is enabled via the spatial proximity and the thus possible interaction between the molecules, or the spin-orbit coupling is generated via a metal atom contained in the emitter.

[1297] 15

[1298] 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, comprise materials from various classes of substances.

[1299] 20

[1300] 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 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.

[1301] Preferred host materials or co-host materials, which in particular

[1302] 30, which are used together with fluorescent dopants, are selected from the classes of oligoarylenes (e.g. 2,2',7,7'-tetraphenylspirobifluorene according to EP 676461 or dinaphthylanthracene), in particular oligoarylenes containing condensed aromatic groups, such as anthracene, benzanthracene, benzphenanthrene (DE 102009005746, WO 09 / 069566),

[1303] 35 Phenanthrene, Tetracene, Coronene, Chrysene, Fluorene, Spirofluorene, Perylene, Foreignfiling_text P24-203.docx

[1304] - 112 -

[1305] Phthaloperylene, naphthaloperylene, decacycles, rubrene, the oligoarylene vinylenes (e.g. DPVBi = 4,4'-bis(2,2-diphenyl-ethenyl)-1,1'-biphenyl) or spiro-DPVBi according to EP 676461), the polypodal metal complexes (e.g. according to WO 04 / 081017), in particular metal complexes of 8-hydroxyquinoline, e.g. B. AlQ3(= Aluminium(III)tris(8-hydroxyquinoline)) or Bis(2-methyl-8-quinolinolato)-4-5(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. 10 (e.g. according to WO 05 / 084081 and WO 05 / 084082), the atropisomers (e.g.

[1306] according to WO 06 / 048268), the boronic acid derivatives (e.g. according to the

[1307] WO 06 / 117052) or the benzanthracenes (e.g. according to WO 08 / 145239).

[1308] 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 pyrene groups are present.

[1309] aryl groups are bonded to each other.

[1310] 20

[1311] Preferred host materials are in particular selected from compounds of formula (H-100),

[1312] Ar 5 -(Ar 6 ) p -Ar 7 (H-100)

[1313] 25

[1314] where Ar 5 , Ar 6 , Ar 7 where, 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 of 1 to 5; 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.

[1315] The Ar group is particularly favored in compounds of formula (H-100). 6 for Anthracenes and the Ar groups 5 and Ar 7 are in 9th and 10th position

[1316] 35 bound, whereby these groups may be substituted if necessary. Entire Foreignfiling_text P24-203.docx

[1317] - 113 -

[1318] At least one of the groups Ar is particularly preferred 5 and / or Ar 7 a fused aryl group selected from 1- or 2-naphthyl, 2-, 3- or 9-phenanthrenyl, or 2-, 3-, 4-, 5-, 6- or 7-benzanthracenyl. Anthracene-based compounds are described in US 2007 / 0092753 A1 and US 2007 / 0252517 A1, e.g. Examples include 2-(4-methylphenyl)-9,10-di-(2-naphthyl)anthracene, 9-(2-5-naphthyl)-10-(1,1'-biphenyl)anthracene, 9,1-O-bis[4-(2,2-diphenylethenyl)phenyl]anthracene, 9,10-diphenylanthracene, 9,10-bis(phenylethynyl)anthracene, and 1,4-bis(9'-ethynylanthraceneyl)benzene. Compounds with two anthracene units are also preferred (US 2008 / 0193796 A1), e.g., 10,10'-bis[1,1',4',1"]ter-phenyl-2-yl-9,9'-bisanthraceneyl.

[1319] 10

[1320] Other preferred compounds are derivatives of arylamine, styrylamine, fluorescein, diphenylbutadiene, tetraphenylbutadiene, cyclopentadiene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, coumarin, oxadiazole, bisbenzoxazoline, oxazole, pyridine, pyrazine, imine, benzothiazole, benzoxazole, benz15imidazole (US 2007 / 0092753 A1), e.g. B. 2,2',2”-(1,3,5-phenylene)tris[1-phenyl-1H-benzimidazole], aldazine, stilbene, styrylarylene 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. 20

[1321] 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.

[1322] 25 Preferred compounds with oligoarylenes as a matrix are set out in US 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, with particularly preferred compounds being described by formulas H-102 to H-108.

[1323] 35 Foreignfiling_text P24-203.docx

[1324] 5

[1325]

[1326] Formula H-102 Formula H-103

[1327] 10

[1328]

[1329] Formula H-104 Formula H-105 15

[1330]

[1331] 20 Formula H-106 Formula H-107

[1332]

[1333] 25

[1334]

[1335] Furthermore, compounds that can be used as a host or matrix include materials that are used together with phosphorescent emitters.30 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, 35 carbazole derivatives, e.g. B. CBP (N,N-Biscarbazolylbiphenyl) or WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 288381, EP 1205527, WO 2008 / 086851 or WO Foreignfiling_text P24-203.docx

[1336] - 115 -

[1337] 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 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 5 2005 / 111172, azaborols or boron esters, e.g. B. 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. according to EP 652273 or WO 2009 / 062578, diazasilol or tetraazasilol derivatives, e.g. according to WO 2010 / 054729, diazaphosphol derivatives, 10 e.g. according to WO 2010 / 054730, bridged carbazole derivatives, e.g. B. according to WO 2011 / 042107, WO 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 example according to US 2021 / 0122765. Likewise, another phosphorescent emitter, which emits at a shorter wavelength than the actual emitter, may be present as a co-host in the mixture, or a compound that does not participate, or does not participate to a significant extent, in charge transport, as described, for example, in WO 2010 / 108579 20.

[1338] The aforementioned publications describing the functional materials which can be used to manufacture functional layers of electronic devices are incorporated into the present application for disclosure purposes by reference 25.

[1339] Furthermore, it may be provided that the electronic device is an organic electroluminescent device and that the electroluminescent device comprises an electron transport layer, wherein the electron transport layer comprises at least an electron transport material and a compound according to formula (I).

[1340] 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 an electron Foreignfiling_text P24-203.docx

[1341] - 116 -

[1342] The electron transport material comprises [the following]. Preferably, the electron transport material is selected from compounds of formulas (E-1) to (E-4) or preferred embodiments of these compounds.

[1343] 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 transport material and a compound according to formula (I).

[1344] Preferably the hole transport layer can be a according to the invention.

[1345] 10. Composition comprising, preferably consisting of, a composition according to the invention, wherein this composition comprises a hole transport material. Preferably, the hole transport material is selected from compounds of formulas (L-1) and / or (L-2) or preferred embodiments of these compounds.

[1346] 15

[1347] The ordinary refractive indices of the layers of an electronic device, preferably an organic electroluminescence device, measured via ellipsometry at 620 nm, are preferably less than 1.75, more preferably less than 1.70, more preferably less than 1.68 and more preferably less than 1.66.

[1348] 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, the person skilled in the art can, without any inventive effort, use all materials known for organic electroluminescent devices in combination with the compounds according to formula (I) or the preferred embodiments described above.

[1349] In addition to the layers described above, an electronic device, 30 preferably an organic electroluminescent device, can comprise further layers. In particular, a compound according to formula (I) or preferred embodiments of this formula can be used to produce an outcoupling layer, a capping layer, or an matching layer. A further 35 preferred subject matter of the present invention is therefore an electronic Foreignfiling_text P24-203.docx

[1350] - 117 -

[1351] Device, preferably an organic electroluminescence device with an outcoupling layer, a capping layer or an matching layer comprising a compound according to formula (I) or preferred embodiments of this formula, preferably consisting of one or more of these compounds.

[1352] 5

[1353] Preferred electroluminescent devices (OLEDs) according to the invention comprise the following layer structure, whereby it is not excluded that further layers are present:

[1354] - Anode

[1355] 10 - Hole Injection Layer (HIL)

[1356] - Hole transport layer (HTL)

[1357] - Electron blocking layer (EBL)

[1358] - Emission layer (EML) containing a fluorescent or phosphorescent dopant

[1359] 15 - Hole-blocking layer (HBL)

[1360] - Electron transport layer (ETL)

[1361] - Electron injection layer

[1362] - Cathode.

[1363] 20 Various embodiments of the invention are summarized in the following table:

[1364] EML connection of formula (I) or

[1365] preferred embodiments in

[1366] 25

[1367] next layer

[1368] 1 fluorescent HIL

[1369] 2 fluorescent HTL

[1370] 3 fluorescent EBL

[1371] 4 fluorescent HBL

[1372] 30

[1373] 5 fluorescent ETL

[1374] 6 fluorescent HIL + HTL

[1375] 7 fluorescent HIL + EBL

[1376] 8 fluorescent HIL + HBL

[1377] 9 fluorescent HIL + ETL

[1378] 35

[1379]

[1380] 10 fluorescent HTL + EBL Foreignfiling_text P24-203.docx

[1381] - 118 -

[1382] 11 fluorescent HTL + HBL

[1383] 12 fluorescent HTL + ETL

[1384] 13 fluorescent EBL + HBL

[1385] 14 fluorescent EBL + ETL

[1386] 15 fluorescent HBL + ETL

[1387] 5

[1388] 16 fluoreszent HIL + HTL + EBL

[1389] 17 fluoreszent HIL + HTL + HBL

[1390] 18 fluoreszent HIL + HTL + ETL

[1391] 19 fluoreszent HIL + EBL + HBL

[1392] 20 fluoreszent HIL + EBL + ETL

[1393] 10

[1394] 21 fluoreszent HIL + HBL + ETL

[1395] 22 fluoreszent HTL + EBL + HBL

[1396] 23 fluoreszent HTL + EBL + ETL

[1397] 24 fluoreszent HTL + HBL + ETL

[1398] 15 25 fluoreszent EBL + HBL + ETL

[1399] 26 fluoreszent HIL + HTL + EBL + HBL 27 fluoreszent HIL + HTL + HBL + ETL 28 fluoreszent HTL + EBL + HBL + ETL 29 fluoreszent HIL + HTL + EBL + HBL + ETL 20 30 phosphoreszent HIL

[1400] 31 phosphoreszent HTL

[1401] 32 phosphoreszent EBL

[1402] 33 phosphoreszent HBL

[1403] 34 phosphoreszent ETL

[1404] 25 35 phosphoreszent HIL + HTL

[1405] 36 phosphoreszent HIL + EBL

[1406] 37 phosphoreszent HIL + HBL

[1407] 38 phosphoreszent HIL + ETL

[1408] 39 phosphoreszent HTL + EBL

[1409] 30 40 phosphoreszent HTL + HBL

[1410] 41 phosphoreszent HTL + ETL

[1411] 42 phosphoreszent EBL + HBL

[1412] 43 phosphoreszent EBL + ETL

[1413] 44 phosphoreszent HBL + ETL

[1414] 35

[1415]

[1416] 41 phosphoreszent HIL + HTL + EBL Foreignfiling_text P24-203.docx

[1417] - 119 -

[1418] 42 phosphoreszent HIL + HTL + HBL

[1419] 43 phosphoreszent HIL + HTL + ETL

[1420] 44 phosphoreszent HIL + EBL + HBL

[1421] 45 phosphoreszent HIL + EBL + ETL

[1422] 46 phosphoreszent HIL + HBL + ETL

[1423] 5

[1424] 47 phosphoreszent HTL + EBL + HBL

[1425] 48 phosphoreszent HTL + EBL + ETL

[1426] 49 phosphoreszent HTL + HBL + ETL

[1427] 50 phosphoreszent EBL + HBL + ETL

[1428] 51 phosphoreszent HIL + HTL + EBL + HBL

[1429] 10

[1430] 52 phosphoreszent HIL + HTL + HBL + ETL

[1431] 53 phosphoreszent HTL + EBL + HBL + ETL

[1432]

[1433] 54 phosphoreszent HIL + HTL + EBL + HBL + ETL

[1434] 15 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 also be a hyperfluorescent EML containing a TADF compound as a sensitizer, or a hyperphosphorescent EML containing a phosphorescent compound as a sensitizer. In another preferred embodiment, the phosphorescent EML is a green, yellow, or red-emitting layer.

[1435] A further preferred organic electroluminescence device is characterized in that one or more layers are coated using a sublimation process. The materials are sublimated in vacuum sublimation systems at an initial pressure of less than 10 -5 mbar, preferably less than 10 -6 The initial pressure is vapor-deposited at mbar. However, it is also possible that the initial pressure is even lower, for example less than 10 mbar. -7 mbar.

[1436] 30. Also preferred is an organic electroluminescence device, characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) process or with the aid of carrier gas sublimation. The materials are coated at a pressure between 10 -5 mbar and 1 bar are applied. A special case of this process is the OVJP 35 (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and thus structured. Foreignfiling_text P24-203.docx

[1437] - 120 -

[1438] A further preferred organic electroluminescence 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.

[1439] Formulations for applying a compound according to formula (I) or its 10 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 its previously described preferred embodiments.

[1440] 15 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.

[1441] 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.

[1442] The compounds and the organic electroluminescence devices according to the invention can, depending on the specific design, be characterized by a low refractive index (RI).

[1443] Furthermore, these compounds and the organic electroluminescent devices obtained from them exhibit an improved lifetime. The other electronic properties of the electroluminescent devices, such as efficiency, remain at least as good. In another embodiment, the compounds and organic electroluminescent devices according to the invention are distinguished from the prior art, in particular, by improved efficiency and / or a longer lifetime.

[1444] 35 Foreignfiling_text P24-203.docx

[1445] - 121 -

[1446] 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:

[1447] 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, with a matrix material, with a hole-conducting material or with an electron-conducting material, exhibit excellent efficiency.

[1448] 10

[1449] 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, 15 with a hole-conducting material or with an electron-conducting material, have a very good lifetime.

[1450] 3. The compounds according to formula (I) or the preferred embodiments described above and below exhibit a very high

[1451] 20 Stability.

[1452] 4. Electronic devices, in particular organic electroluminescent devices containing compounds according to formula (I) or the preferred embodiments described above and below, exhibit a very low refractive index of 25.

[1453] 5. With compounds according to formula (I) or the preferred embodiments described above and below, the formation of losses due to optical reflection can be avoided in electronic devices, in particular organic electroluminescent devices 30.

[1454] 6. Compounds according to formula (I) or the preferred embodiments described above and below exhibit excellent glass film formation.

[1455] 35 Foreignfiling_text P24-203.docx

[1456] - 122 -

[1457] 7. Compounds according to formula (I) or the preferred embodiments described above and below form very good films from solutions.

[1458] These advantages mentioned above do not come at the cost of an excessively high deterioration of other electronic properties.

[1459] 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.

[1460] 15

[1461] 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 that are not essential to the invention can be used separately (and not in combination).

[1462] It should also 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 the embodiments of the present invention. Independent protection may be sought for these features in addition to or as an alternative to any invention currently claimed.

[1463] The teaching on technical action disclosed in the present invention 30 can be abstracted and combined with other examples.

[1464] The invention is further explained by the following examples, without thereby limiting it. The person skilled in the art can implement the invention in its entire disclosed scope from the descriptions and, without inventive effort, create further compounds according to the invention and describe them in Foreignfiling_text P24-203.docx

[1465] - 123 -

[1466] use electronic devices or apply the method according to the invention.

[1467] Examples:

[1468] 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 information in square brackets and the numbers given for individual compounds refer to the CAS numbers of the compounds known from the literature. For compounds that can have several isomeric, enantiomeric, diastereomeric, or tautomeric forms, one form is shown as a representative example.

[1469] 15

[1470] 20

[1471] 25

[1472]

[1473] 30

[1474] 35

[1475]

[1476] Foreignfiling_text P24-203.docx

[1477] - 124 -

[1478] xj / J /

[1479] \ TIIT / i \ S r i 1 1 Ho — Si— Si — Si— Si — Si — Si — — Si— Si— Si— Si-Si— Si — Si — — Si— Si— Si-Si-Si-Si— Si— SI — / Si 1 1 Si / . SI III u. i 1 UC

[1480] 78365-62-5 607691-56-5 78365-63-6 5

[1481] B B6 B4 5

[1482] — \ SSi— r i 1 / \ TII \ II I. | Si— Si— Si — Si — — Si-Si— Si-Si — — Si— Si— Si-Si-Si — / 1 1 A / >, II / A l I l 10

[1483] 326480-04-0 26037-23-0 78365-57-8 B7 B8 B9

[1484] \S r i I |V / ^1 / — Si— Si— Si-Si-Si— Si— SI — \S r i 1 1 / \ 1 1 1 l' / / II | II \ 15 — S i— S i — S i— S i — S i — Si — — Si— Si — Si— Si — Si —

[1485] \ —Si — \ l / 1 1 1 1 1 1 \ -Si-Si —

[1486] / I

[1487] / SL 50965-63-4 78365-60-3

[1488] B10 B11 162411-16-7

[1489] B12 20

[1490] r-,, \ 1 1 1 / II / — Si-Si — Si-Si-Si — Si— Si — x / Sl ^Si— Si-Si—

[1491] \ / / ' A l IIA x You You You _\. I / s ^ I \ —Si— / I

[1492] \. I. / from Sl " Si-^ ' — Si — Si— Si — ' Cs'i 25

[1493] n

[1494] 187084-81-7 173603-20-8161065-60-7 B15

[1495] B14 B13

[1496] >-- / ^Si^, 7^ / ^Si^\---' /

[1497] \ I. / \ \ I / / - \ / 30 ) — Si Si — Si — — Si— Si— Si — / / I \ / yiv \

[1498] -'-"' X / SL

[1499] 412295-36-4 412295-17-1 221218-42-4 B17 B16 B18

[1500]

[1501] 35 Foreignfiling_text P24-203.docx

[1502] - 125 -

[1503] 1314029-96-3 5 B21

[1504] 10

[1505] 15

[1506] 20

[1507] 25 104475-58-3 104475-59-4 135877-94-0

[1508] B29 B30

[1509] 30

[1510] 688360-62-5

[1511] 82615-12-1

[1512] B32 110209-62-5 B31

[1513] 35

[1514]

[1515] B33 Foreignfiling_text P24-203.docx

[1516] - 126 -

[1517] Yes Yes : - with

[1518] Yes

[1519] :yes yes : / Yes Yes. Yes

[1520] \ / ;si \ / : Si \ / Si;. Si—Si.

[1521] 79769-58-7 99148-09-1 99148-11-5 5

[1522] B34 B35 B36

[1523] — S< Sr

[1524] :sr s ^ Yes.

[1525] — Yes. Yes — ' Yes

[1526] 10

[1527] 954116-60-0 99548-02-4 13452-94-3 B37 B38 B39

[1528] ■s / r Si

[1529] Si 15: SK Si *

[1530] - S Ci i / Si \ / ' / jSi~~. Q i 'y / si Si Si— Si-_ / _^Si— Si-^ \

[1531] 139328-85-1 1085962-17-9 272123-25-8 B41 B42 20 B40

[1532] — Yes— Yes Yes— Yes — — Yes — Yes \ Yes — Yes — Yes — Yes — Yes — Yes — Yes / jYes— \ — Yes / -|Yes —

[1533] 25 79769-61-2 1231960-89-6

[1534] B43 B44

[1535] \ J / \. J / I \ jT / C'T / — Si— Si— Si — Si — Si— Si - Si - Si - Si - Si — Si— Si —

[1536] U ' I

[1537] \ l^ /

[1538] 30 — Yes— Yes— Yes —

[1539] — Yes-Yes— Yes —

[1540] 162411-16-7

[1541] 215435-40-8

[1542] 35 B45

[1543]

[1544] B46 Foreignfiling_text P24-203.docx

[1545] - 127 -

[1546] 3s( / J-^Si Si~ \ / . Si(

[1547] \ from Si - / s< ^Si^ z Sl "- \ / \i^ " Si | / ■

[1548] CX icz s \ — si- si— 4 / / S >[ — =81- Si- Si— 1 / < / 1 k / 1 X ' / " A / Si \ / I -"" Yes Yes YES X '^ / \n / sr"

[1549] n "7 S \

[1550] 258851-82-0 Organometallics 1996, 15, 615 B47 B48

[1551] -XX

[1552] Xjc 3 ^

[1553] , Sk II \ / \ Si v /

[1554] I II / I. / — S i- S i- S i- S iS i — S i — S i— Si— Si— Si S i — ^Si ^si' S 'Yes— z I / I | I^ |

[1555] l \ I /

[1556] — Si-Si-Si— \ \ -Si-Si- 1 — Si— Si— Si— Si — / cL Z JV / \Ui^r

[1557] \ ^i\ -Si-Si—

[1558] ^Si-Si^sC /

[1559] / SL \

[1560] 221378-93-4 215435-40-8

[1561] B50

[1562] B49

[1563] III

[1564] \ IIII "§ |_ | I §' /

[1565] -Si-Si— Si-Si-Si— Si— Si-Si — Si-Si-Si— Si Si—

[1566] z ^sM 1 — you— ' 1 1 -si- ' 1

[1567] 1 1 -Si- 1 1

[1568] —SrSrSi—

[1569] - 1 S Ji- 1

[1570] 1

[1571] — Si—

[1572] \. 1. /

[1573] — SrSrSi—

[1574] 7 / Si J

[1575] 1

[1576] 215435-40-8

[1577]

[1578] B51

[1579] 35 Foreignfiling_text P24-203.docx

[1580] - 128 -

[1581] \^§ r /

[1582] — Si-Si-Si—

[1583] 5

[1584] 1007228-03-6

[1585] B52

[1586] 10

[1587] 198419-02-2

[1588] B53

[1589] 15 " Yes Yes

[1590] — S i — S i — S i — S i — S i — S i — S i — S i — S i — S i—

[1591] I.. I l l

[1592] Si

[1593] 1070904-53-8

[1594] 20 B54

[1595] — S i — S i — S i — S i — S i — S i S i S i S i — S i — S i — S i — S i — S i — S i — S i— I I I I I I I I I I I I I I I I

[1596] 132316-94-0

[1597] 25

[1598] 30 872178-45-5

[1599]

[1600] B56

[1601] 35 Foreignfiling_text P24-203.docx

[1602] - 129 -

[1603] 5

[1604] 10

[1605] 15

[1606] 20

[1607] 25

[1608]

[1609] C: Polymere Schichten

[1610] Beispiel PS1:

[1611] 30

[1612] 1 g of S3 and 10 mg of azobis(isobutyronitrile) [78-67-1] are dissolved in 50 ml of 1-methoxy-2-propyl acetate [108-65-6] at 20 °C. Clean quartz glass plates (50 x 50 mm, cleaned in a Miele laboratory dishwasher with Merck Extran cleaner, then activated by UV / ozone plasma treatment) are coated with this solution by dip-coating or spin-coating (layer thicknesses typically 20 nm).

[1613] until 1 pm, the required spin rate depends on the dilution level and the specific Foreignfiling_text P24-203.docx

[1614] - 130 -

[1615] (Spin coater geometry is applied). After 15 minutes of drying, the glass plates are placed in an oven at 180 °C for 30 minutes. After cooling, homogeneously coated plates are obtained, which appear crystal clear to the naked eye. The ordinary refractive index is determined using an ellipsometer (JA Wollam Inc., USA) at a wavelength of 620 nm; the value is calculated from the dispersion curve to be 1.56.

[1616] Example PS2:

[1617] The procedure is analogous to example PS1, except that S4 is used instead of S3.

[1618] Refractive index: 1.55.

[1619] 10

[1620] Example PS3:

[1621] Procedure analogous to example PS1, except that S5 is used instead of S3.

[1622] Refractive index: 1.55.

[1623] 15 Example PS4:

[1624] Procedure analogous to example PS1, except that 0.9 g of S5 and 0.1 g of S1 are used instead of S3. Refractive index: 1.56.

[1625] Example PS5:

[1626] 20. Procedure analogous to example PS1, using 0.9 g of S5 and 0.1 g of S2 instead of S3. Refractive index: 1.55.

[1627] Examples of devices

[1628] In the following examples, OLEDs according to the invention (Example Exa1 25 to 4 and Exb1 to 3) and an OLED according to the prior art (comparative examples Va1 and Vb1) are produced. The exact structure of the OLEDs can be found in Tables 1a and b. The materials used to produce the OLEDs are shown in Table 2. The properties of the OLEDs according to the invention of Examples Exa1 to Exa4 and Exb1 to Exb3 and the properties of OLED 30

[1629] The state of the art is listed in Tables 3a and 3b.

[1630] Manufacturing of OLEDs

[1631] Glass plates coated with structured ITO (indium tin oxide) 50 nm thick are used as substrates for the OLEDs.

[1632] 35

[1633] Materials are thermally vapor-deposited in a vacuum chamber. (Foreignfiling_text P24-203.docx)

[1634] - 131 - 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 specification such as BH:BD (98:2) 20 nm means that the material BH is present in a

[1635] 5. The host material comprises 98% by volume, with the compound BD present in a 2% by volume layer within a 20 nm thick layer. Similarly, the hole injection layer (HIL), the hole transport layer (HTL), and 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 Table 1a and Table 1b.

[1636] depicted.

[1637] Table 1a:

[1638] HIL HTL EBL EML HBL ETL EIL

[1639] Example.

[1640] Dicke Dicke Dicke Dicke Dicke Dicke Dicke 15

[1641] HTM1: PD BH: BD ETM1: LiQ HTM1 EBM HBM LiQ Va1 (95:5) (98:2) (50:50)

[1642] 185 nm 5 nm 5 nm 3 nm 15 nm 20 nm 35 nm HTM1: PD BH: BD ETM1: B13

[1643] HTM1 EBM HBM LiQ Exa1 (95:5) (98:2) (50:50)

[1644] 185 nm 5 nm 5 nm 3 nm 15 nm 20 nm 35 nm

[1645] 20 HTM1: PD BH: BD ETM1: B48

[1646] HTM1 EBM HBM LiQ Exa2 (95:5) (98:2) (50:50)

[1647] 185 nm 5 nm 5 nm 3 nm 15 nm 20 nm 35 nm HTM1: PD BH: BD ETM1: B107

[1648] HTM1 EBM HBM LiQ Exa3 (95:5) (98:2) (50:50)

[1649] 185 nm 5 nm 5 nm 3 nm 15 nm 20 nm 35 nm

[1650] 25 HTM1: PD BH: BD ETM1: LiQ: B48

[1651] HTM1 EBM HBM LiQ Exa4 (95:5) (98:2) (50:10:40)

[1652] 185 nm 5 nm 5 nm 3 nm 15 nm 20 nm 35 nm HTM1: PD BH: BD ETM1: B48

[1653] HTM1 EBM HBM LiQ Exa5 (95:5) (98:2) (50:50)

[1654] 185 nm 5 nm 5 nm 3 nm 15 nm 20 nm 35 nm HTM1: PD BH: BD ETM1: B48

[1655] 30 HTM1 EBM HBM LiQ Exa6 (95:5) (98:2) (40:60)

[1656] 185 nm 5 nm 5 nm 3 nm 15 nm 20 nm 35 nm HTM1: PD BH: BD ETM1: B48

[1657] HTM1 EBM HBM LiQ Exa7 (95:5) (98:2) (40:60)

[1658] 185 nm 5 nm 5 nm 3 nm

[1659]

[1660] 15 nm 20 nm 35 nm

[1661] 35 Tabelle 1b: Foreignfiling_text P24-203.docx

[1662] - 132 - HIL HTL EBL EML HBL ETL EIL

[1663] Bsp.

[1664] Dicke Dicke Dicke Dicke Dicke Dicke Dicke HTM1: PD BH: BD ETM1: LiQ HTM1 EBM HBM LiQ Vb1 (95:5) (98:2) (50:50)

[1665] 190 nm 5 nm 5 nm 1 nm 15 nm 20 nm 30 nm HTM1: PD HTM1: B13 BH: BD ETM1: LiQ EBM HBM LiQ 5 Exb1 (95:5) (65:35) (98:2) (50:50)

[1666] 5 nm 5 nm 1 nm 15 nm 190 nm 20 nm 30 nm HTM1: PD HTMTB48 BH: BD ETM1: LiQ EBM HBM LiQ Exb2 (95:5) (65:35) (98:2) (50:50)

[1667] 5 nm 5 nm 1 nm 15 nm 190 nm 20 nm 30 nm HTM1: PD HTMTB107 BH: BD ETM1: LiQ EBM HBM LiQ Exb3 (95:5) (65:35) (98:2) (50:50)

[1668] 10 5 nm 5 nm 1 nm 10 nm 190 nm 20 nm 30 nm HTM2: PD HTM2: B48 BH: BD ETM1: LiQ EBM HBM LiQ Exb4 (95:5) (65:35) (98:2) (50:50)

[1669] 5 nm 5 nm 1 nm 10 nm 190 nm 20 nm 30 nm HTM3: PD HTMTB48 BH: BD ETM1: LiQ EBM HBM LiQ Exb5 (95:5) (65:35) (98:2) (50:50)

[1670] 15 5 nm 5 nm 1 nm

[1671]

[1672] 10 nm 190 nm 20 nm 30 nm

[1673] Tabelle 1c:

[1674] HIL HTL EBL EML HBL ETL EIL

[1675] Bsp.

[1676] Dicke Dicke Dicke Dicke Dicke Dicke Dicke HTM1: PD BH: BD ETM1: LiQ

[1677] 20 HTM1 EBM HBM LiQ Vc1 (95:5) (97:3) (50:50)

[1678] 190 nm 5 nm 5 nm 3 nm 10 nm 20 nm 35 nm HTM1: PD HTMTB48 BH: BD ETM1: B4

[1679] EBM HBM LiQ Exc1 (95:5) (65:35) (97:3) 8 (50:50)

[1680] 5 nm 5 nm 3 nm

[1681]

[1682] 10 nm 195 nm 20 nm 35 nm

[1683] 25

[1684] Table 2: OLED Materials

[1685] F

[1686] \ >-CN O

[1687] UF NC. JL, F \\ F F

[1688] 30 J TI An A F \ A

[1689] F^yy^

[1690] F CN /

[1691] NC p r U PD [1224447-88-4]

[1692]

[1693] HTM1 [136463-07-5]

[1694] 35 Foreignfiling_text P24-203.docx

[1695] - 133 - o O rA oz\=

[1696] —

[1697] rQ Q N OX f OMn w _ 5 ^ z H o O / LiX-) / \°

[1698] HTM2 [p1 o364603-07-5] HTM3 [2356086-92-3] 0 o

[1699] 0 *

[1700] 10 = / =, 0 o

[1701] / \ ==

[1702] LA

[1703] m=A A)

[1704] EBM LiQ [25387-93-3]

[1705] 15 o

[1706] CuO z-o-x Q rV QOOu h Q p ^^AQMOQc p o

[1707] M< / =

[1708] BH [1087346-88-0] BD [1182175 O-27-4] 20 o

[1709] ) \ r =~ / \V\ = J = \ v >~N / =\ z N =< < 7 N \\ — / A

[1710] 25 O d < w f vO

[1711] 0

[1712] HBM [1955543-57-3] ETM1 [1233200-52-6]

[1713] 30

[1714]

[1715] ETM2 ETM3

[1716] 35 Foreignfiling_text P24-203.docx

[1717] - 134 - Q _

[1718] p y 0

[1719] rv-O O

[1720] 5 0^0

[1721] ETM4

[1722] J^Si

[1723] \ 1 1 1 / \ l \ i / 10 — Si-Si — Si-Si-Si — Si— Si— PA Z S'- \ / siP C z

[1724] ' A Si \ | / \

[1725] 1 1 A x

[1726] 1 \ — Si— / 1 z s \

[1727] \ 1 / \ / I SA Si< / — Si— Si— Si — A / I "" Si Si / Si S< A \ I x -si

[1728] 15 / \ / ^

[1729] 161065-60-7 Organometallics 1996, 15, 615 B13 B48

[1730] — Si— Si^ /

[1731] > \' / \

[1732] 20 — Yes— Yes.

[1733] 0 \ z /

[1734] <p~ s \ /

[1735] Yes Yes —

[1736] / \ /

[1737] / Yes— Yes —

[1738] 25 299438-08-7

[1739]

[1740] B107

[1741] Characterization of OLEDs

[1742] The OLEDs are characterized according to standard procedures. For this, the electroluminescence spectra and current-voltage-luminance (IUL) curves are measured, and the EQE is calculated from these measurements. The calculation assumes a Lambertian emission characteristic. The electroluminescence spectra are measured at a luminance of 1000 cd / m². 2 The CIE 1931 x and y color coordinates were determined and calculated from this. The voltage, which corresponds to a current density of 10 mA / cm² for 35°, is then used. 2 The required file is referred to here as U10. Foreignfiling_text P24-203.docx

[1743] - 135 - EQE10 denotes the external quantum efficiency at a current density of 10 mA / cm² 2 .

[1744] For each example, the relative EQE and the relative voltage are calculated in comparison to the respective reference example:

[1745] 5 relative U (Ex) = (U10(Ex) / U10(V))

[1746] rel. EQE (Ex) = (EQE10(Ex) / EQE10(V))

[1747] The refractive index (RI) of a layer at a wavelength of 620 nm is determined using ellipsometry (JA Wollam Inc., USA). The measurement comprises 10

[1748] The wavelength range from 250 nm to 1000 nm and the respective refractive index are determined via dispersion curves. Samples for determining the refractive index (RI) are produced on SiÜ2 substrates with three different layer thicknesses. The respective material is thermally vapor-deposited. From these measurements, the mean value of the 15

[1749] Refractive index determined for each material or material mixture.

[1750] The results are shown in the following tables 3a, 3b and 3c.

[1751] 20 Table 3a: Properties of OLEDs

[1752] relative relative

[1753] BeiCIE x / y at RI ETL*

[1754] EQE10

[1755] game U10 (%) 1000 cd / m 2 @ 620 nm

[1756] (%)

[1757] Va1 1.00 1.00 0.13 / 0.13 1.71

[1758] 25 Exa1 1.02 1.05 0.13 / 0.13 1.68

[1759] Exa2 1.02 1.06 0.13 / 0.14 1.66

[1760] Exa3 1.01 1.07 0.13 / 0.14 1.66

[1761] Exa4 1.01 1.07 0.13 / 0.13 1.67

[1762] Exa5 1.02 1.06 0.13 / 0.14 1.66 30

[1763] Exa6 1.01 1.08 0.13 / 0.13 1.66

[1764] Exa7 1.00 1.09 0.13 / 0.14 1.65

[1765] (* of the complete ET L layer of the OLED)

[1766]

[1767] Table 3b: Properties of OLEDs 35 Foreignfiling_text P24-203.docx

[1768] relative relative

[1769] At CIE x / y at RI HTL*

[1770] EQE10

[1771] game U10 (%) 1000 cd / m 2 @ 620 nm

[1772] (%)

[1773] Vb1 1.00 1.00 0.14 / 0.13 1.73

[1774] Exb1 1.00 1.05 0.14 / 0.13 1.68

[1775] 5 Exb2 1.01 1.07 0.14 / 0.13 1.68

[1776] Exb3 1.02 1.06 0.14 / 0.14 1.67

[1777] Exb4 1.01 1.06 0.14 / 0.13 1.68

[1778] Exb5 1.00 1.08 0.14 / 0.14 1.67

[1779] (* of the complete HT L layer of the OLED) 10

[1780] Table 3c: Properties of OLEDs

[1781] relative relative CIE x / y at BeiEQE10

[1782] game U10 (%) 1000 cd / m 2

[1783] (%)

[1784] 15 Vc1 1.00 1.00 0.14 / 0.13

[1785] Exc1 1.04 1.09 0.14 / 0.13

[1786]

[1787] When comparing the examples according to the invention Exa1 to Exa4 and Exb1 to Exb3 and Exc1 with the corresponding comparative example Va1 or Vb1 or 20

[1788] Vc1, it is clearly evident that the OLED according to the invention exhibits a significant advantage in device efficiency, without negatively affecting lifetime, voltage, or color. This surprising finding may possibly be due to the lower refractive index of 1.56 of the material B13 added according to the invention, 1.55 of material B48, and 1.55 of 25.

[1789] Materials B107 can be traced back to this without any restriction being imposed. In comparison, LiQ in comparison example Va1 and Vc1 has a refractive index of 1.65 and the HTM in Vb1 and Vc1 has a refractive index of 1.73.

[1790] 30

[1791] E: Device examples for green phosphorescent OLEDs

[1792] In the following three examples, OLEDs according to the invention (examples gE1a-c, gE2a-b, gE3a and gE4a) and one OLED according to the prior art (comparative examples gC1, gC2, gC3 and gC4) are produced. The exact 35

[1793] The structure of the OLEDs can be found in Table 4. The [document] used to manufacture the Foreignfiling_text P24-203.docx

[1794] - 137 - The materials used in OLEDs are shown in Table 5. The properties of the OLEDs according to the invention and the comparative examples are summarized in Table 6.

[1795] Production of green OLEDs

[1796] 5. Glass platelets coated with structured ITO (indium tin oxide) with a thickness of 50 nm are used as substrates for the OLEDs. All 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 (10).

[1797] The emitter is added to the matrix material(s) by cover evaporation in a specific volume fraction. A specification such as GH1:GH2:GE (32:60:8) means that material GH1 is present in a volume fraction of 32% as host material 1, GH2 in a volume fraction of 15% as host material 2, and the compound GE in a volume fraction of 8%. Similarly, the hole injection layer (HIL), hole transport layer (HTL), electron blocking layer (EBL), hole blocking layer (HBL), and electron transport layer (ETL) can also consist of a mixture of two or more materials. The structure of the respective OLEDs is shown in Table 4, and materials for green OLEDs are shown in Table 5. After the electron injection layer (EIL) is deposited, a 100 nm aluminum cathode is deposited onto each component.

[1798] Table 4: Structure of OLEDs

[1799] 25

[1800] Bsp. HIL HTL EBL EML HBL ETL EIL Dicke Dicke Dicke Dicke Dicke Dicke Dicke HTM6: PD GH1: GH2: GE ETM5: LiQ HTM6 HTM6 HBM LiQ gci (95:5) (32:60:8) (50:50)

[1801] 50 nm 30 nm 5 nm 1 nm 12 nm 35 nm 32 nm HTM6: PD HTM6: B48 GH1: GH2: GE ETM5: LiQ HTM6 HBM LiQ 30 gE1a (95:5) (75:25) (32:60:8) (50:50)

[1802] 30 nm 5 nm 1 nm 12 nm 50 nm 35 nm 32 nm HTM6: PD HTM6: B48 GH1: GH2: GE ETM5: LiQ HTM6 HBM LiQ gEib (95:5) (75:25) (32:60:8) (50:50)

[1803] 50 nm 5 nm 1 nm 12 nm 30 nm 35 nm 32 nm HTM6: PD HTM6: B48 HTM6: B48 GH1: GH2: GE ETM5: LiQ HBM LiQ gEic (95:5) (75:25) (75:25) (32:60:8) (50:50)

[1804] 35 5 nm 1 nm

[1805]

[1806] 20 nm 50 nm 30 nm 35 nm 32 nm Foreignfiling_text P24-203.docx

[1807] HTM6: PD GH1: GH2: GE ETM2: LiQ HTM6 HTM5 HBM LiQ gC2 (95:5) (32:60:8) (50:50)

[1808] 50 nm 30 nm 7 nm 3 nm 12 nm 35 nm 30 nm HTM6: PD GH1: GH2: GE ETM2: B48: LiQ HTM6 HTM5 HBM LiQ gE2a (95:5) (32:60:8) (50:45:5)

[1809] 50 nm 30 nm 7 nm 3 nm 12 nm 35 nm 30 nm

[1810] 5 HTM6: PD HTM5: B107 GH1: GH2: GE Md ETM2: B48: LiQ HTM6 HBM LiQ gE2b (95:5) (70:30) (32:60:8) (50:45:5)

[1811] 50 nm 7 nm 3 nm 12 nm 30 nm 35 nm 30 nm HTM6: PD GH1: GH2: GE ETM3: LiQ HTM6 HTM5 HBM LiQ gC3 (95:5) (32:60:8) (50:50)

[1812] 50 nm 30 nm 5 nm 3 nm 12 nm 35 nm 30 nm HTM6: PD GH1: GH2: GE ETM3: B13 10 HTM6 HTM5 HBM LiQ gE3a (95:5) (32:60:8) (50:50)

[1813] 50 nm 30 nm 5 nm 3 nm 12 nm 35 nm 30 nm HTM2: PD GH1: GH2: GE ETM4: LiQ HTM2 HTM4 HBM LiQ gC4 (95:5) (32:60:8) (50:50)

[1814] 50 nm 30 nm 5 nm 3 nm 12 nm 35 nm 32 nm HTM2: PD HTM2: B13 GH1: GH2: GE ETM4: LiQ 15 HTM4 HBM LiQ gE4a (95:5) (70:30) (32 J:60:8) (50:50)

[1815] 30 nm 5 nm 3 nm

[1816]

[1817] 12 nm 50 nm 35 nm D uO 32 nm

[1818] Table 5: Structures of the materials used for the green OLEDs (in addition to the materials of blue OLEDs, see Table 2)

[1819] 20 o

[1820] 25

[1821] HTM4 HTM5

[1822] op

[1823] 30

[1824]

[1825] HTM6 GH1

[1826] 35 Foreignfiling_text P24-203.docx

[1827] - 139 -

[1828] 5

[1829] 10

[1830] 15

[1831]

[1832] Characterization of green OLEDs

[1833] The OLEDs are characterized using standard procedures. This is done analogously to the characterization of the blue OLEDs. The results are summarized in Table 6.20.

[1834] Table 6: OLED results

[1835] relative relative CIE x / y in example

[1836] U10 EQE10 1000 cd / m 2

[1837] 25

[1838] gC1 1.00 1.00 0.36 / 0.61 gE1a 1.00 1.04 0.36 / 0.61 gE1b 1.01 1.05 0.36 / 0.62 gElc 1.02 1.08 0.36 / 0.62 30 gC2 1.00 1.00 0.37 / 0.61

[1839] gE2a 1.01 1.03 0.37 / 0.61 gE2b 1.01 1.09 0.37 / 0.61 gC3 1.00 1.00 0.34 / 0.64 gE3a 1.02 1.03 0.34 / 0.63 35

[1840]

[1841] Foreignfiling_text P24-203.docx

[1842] - 140 - gC4 1.00 1.00 0.36 / 0.61

[1843] gE4a 1.01 1.04 0.36 / 0.62

[1844]

[1845] When comparing the examples gE1a-c, gE2a-b, gE3a and gE4a according to the invention with the corresponding comparison examples gC1, gC2, gC3 and gC4, it is clearly evident that the OLEDs according to the invention show a significant advantage in device efficiency, without negatively affecting lifetime, voltage and color.

[1846] 10

[1847] 15

[1848] 20

[1849] 25

[1850] 30

[1851] 35< / y>

Claims

Foreignfiling_text P24-203.docx - 141 - Patent claims 1. Use of a compound according to formula (I) R c 5 Formula (I) 10 where the following applies to the symbols: R a In each occurrence, it is either a straight-chain alkyl group with 1 to 40 carbon atoms, a branched or cyclic alkyl group with 3 to 40 carbon atoms, or an alkenyl group with 2 to 15 carbon atoms. 40 carbon atoms, each of which can be substituted with F, D or a crosslinkable group; two R groups can be present. a form a ring; R b In each instance, R represents the same or different values. a , Si(R a )3 or 20 OSi(R a )3; where two remainders R can be b or a remainder R b with a remainder R a form a ring; R cIn each instance, R represents the same or different values. a , Si(R a )3, 25 OSi(R a )3, OR a , (Si(R b )2)s(R b ), O(Si(R b )2)s(R b ), (OSi(R b )2) s (R b ), (C(R d )2) r (Si(R b )2) s (R b ), (Si(R b )2)s(C(R d )2) r (Si(R b )2) s (R b ), (C(R d )2) r O(Si(R b )2) s (R b ), (Si(R b )2) r O(Si(R b )2)s(R b ); where two remainders R can be formed c or a remainder R c with a remainder R a or R b form a ring; 30 R d In each instance, it stands for H, D, F, R, either the same or different. a , Si(R a )3 or OSi(R a )3; where two remainders R can be d or a remainder R dwith a remainder R a or R b form a ring; r is an integer in the range of 1 to 20; 35 Foreignfiling_text P24-203.docx - 142 - s is an integer in the range of 1 to 20; t is an integer in the range of 1 to 20; in an electronic device. 5 2. Use according to claim 1, characterized in that the compound according to formula (I) is used in an electroluminescent device. 10 3. Use according to claim 1 or 2, characterized in that the compound corresponds to formula (II), 15 Formula (II) 20 where the symbols t, R a , R b and R c have the meanings mentioned in claim 1.

4. Use according to one or more of claims 1 to 3, characterized in that the crosslinkable group by which the remainder R a substi25 may be chosen from a terminal or cyclic alkenyl or terminal dienyl or alkynyl group, an alkenyloxy, dienyloxy or alkynyloxy group, an acrylic acid group, an oxetane or oxirane group, a silane group or a cyclobutane group. 30 5. Use according to one or more of claims 1 to 4, characterized in that R a The group chosen is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl or tetradecyl, where these groups may be deuterated. 35 Foreignfiling_text P24-203.docx - 143 - 6. Use according to one or more of claims 1 to 5, characterized in that at least two of the residues R b and / or R c for Si(R a )3 or (Si(R b)2) s (R a ) stand.

7. Use according to one or more of claims 1 to 6, characterized in that the compound according to formula (I) has at least two Si atoms which have at least three covalent bonds to Si atoms.

8. Use according to one or more of claims 1 to 7, characterized in that the compound according to formula (I) comprises at least one Si atom having at least four covalent bonds to Si atoms.

9. Use according to one or more of claims 1 to 8, characterized in that the compound according to formula (I) comprises at least two groups of formula Si(R) a )3 includes, where the remainder is R a stands for ethyl, CD2CD3, methyl or CD3.

10. Composition comprising at least one compound according to formula (I) set out in claim 1 and 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.

11. Composition according to claim 10, characterized in that the composition comprises at least one hole injection material or hole transport material selected from compounds of formulas 30 (L-1) and / or (L-2), Ar 15 Ar 15 x Ar 15 N—Ar 16 —N Ar 15 'Ar 15 Ar 15 35 _ (L-1) _ _ (L-2) _ Foreignfiling_text P24-203.docx - 144 - where the following applies to the symbols: Ar 15 In each occurrence, whether the same or different, it is selected from aromatic ring systems with 6 to 50 aromatic ring atoms, the 5 of 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; 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 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 different from H, substituted 15; 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)R 16 , 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 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 -, -C=C-, Si(R 16 )2, C=O, C=NR 16 , -C(=O)O-, -C(=O)NR 16 -, 30 NR 16 , P(=O)(R 16 ), -O-, -S-, SO or SO2; where two or more residues R can be present. 15together form a ring system; R 16 is chosen from H, D, F, C(=O)R for each occurrence, whether the same or different. 17 , CN, Si(R 17 )3, N(R 17 )2, P(=O)(R 17 )2, OR 17 , S(=O)R 17 , 35 S(=O)2R 17 , straight-chain alkyl or alkoxy groups with 1 to 20 C- Foreignfiling_text P24-203.docx - 145 - 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 encapsulated by R groups 17can 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 17 C=CR 17 -, -C=C-, Si(R 17 )2, C=O, 10 C=NR 17 , -C(=O)O-, -C(=O)NR 17 -, NR 17 , P(=O)(R 17 ), -O-, -S-, SO or SO2; where two or more residues R can be present. 16 together form a ring system; R 17 is chosen in each occurrence, either the same or different, from H, D, F, Cl, 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 20, where two or more residues R 17 together form a ring system.

12. Composition according to claim 10 or 11, characterized in that the composition comprises at least one electron transport material 25 selected from compounds of formulas (E-1) to (E-4) (E-1) and (E-2) formula structures as shown in image 35 _ (E-3) _ _ (E^) _ Foreignfiling_text P24-203.docx - 146 - where the symbol R 15 , which has the meaning previously mentioned in claim 11 and for which the following applies: Ar 18 is selected 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 50 aromatic ring atoms separated by R groups 15 can be substituted with something other than H. 10 13. Electronic device comprising at least one connection according to the formula (I) set out in claim 1.

14. Electronic device according to claim 13, wherein the electronic device is an organic electroluminescent device and the electroluminescent device comprises an electron transport layer, the electron transport layer comprising at least one electron transport material and a compound according to formula (I).

15. Electronic device according to claim 13 or 14, wherein the electronic device is an organic electroluminescent device and the electroluminescent device comprises a hole transport layer, the hole transport layer comprising at least a hole transport material and a compound according to formula (I). 25 30

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