Nitrogen-containing heterocyclic compounds for organic electroluminescent devices

Abstract

The present invention relates to nitrogen-containing heterocyclic compounds suitable for use in electronic devices, and electronic devices, in particular organic electroluminescent devices, containing these heterocyclic compounds.

Description

[0001] This invention relates to nitrogen-containing heterocyclic compounds for use in electronic devices, particularly organic electroluminescent devices, and electronic devices comprising these materials, particularly organic electroluminescent devices.

[0002] The luminescent materials used in organic electroluminescent devices (OLEDs) are typically phosphorescent organometallic complexes. Due to quantum mechanical reasons, using organometallic compounds as phosphorescent emitters can achieve up to four times the energy efficiency and power efficiency. However, improvements are still generally needed in electroluminescent devices, especially those exhibiting triplet emission (phosphorescence). The performance of phosphorescent electroluminescent devices is not solely determined by the triplet emitter used. More specifically, other materials used, such as the matrix material, are also particularly important. Therefore, improvements to these materials can also lead to significant improvements in the performance of electroluminescent devices.

[0003] In addition to the light-emitting layer, many electroluminescent devices contain 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 impact on the performance of the electroluminescent device.

[0004] The electroluminescent device detailed above belongs to the technology described in document US 2023 / 0301182 A1.

[0005] Generally speaking, improvements are still needed in the case of these materials, such as when they are used as matrix materials, especially in terms of device lifespan, efficiency, and operating voltage.

[0006] Therefore, the object of the present invention is to provide compounds suitable for use in organic electronic devices, especially organic electroluminescent devices, and which result in good device performance when used in such devices, and to provide corresponding electronic devices.

[0007] More specifically, the problem addressed by this invention is to provide compounds that result in high lifetime, good efficiency, and low operating voltage. In particular, electron injection materials, electron transport materials, and hole blocking materials contribute to these properties. Furthermore, the properties of the matrix material (also referred to herein as the host material) also have a significant impact on the lifetime and efficiency of organic electroluminescent devices.

[0008] Furthermore, the object of the present invention is to provide a compound having a low refractive index (RI).

[0009] Another object of the present invention is to provide compounds suitable for phosphorescent or fluorescent electroluminescent devices, particularly as matrix materials. In particular, the object of the present invention is to provide matrix materials suitable for green or blue phosphorescent electroluminescent devices and also suitable for red or yellow phosphorescent electroluminescent devices.

[0010] Furthermore, the compounds, especially when used as host materials, electron injection materials, electron transport materials or hole blocking materials in organic electroluminescent devices, should result in devices with excellent color purity.

[0011] Another objective can be seen as providing electronic devices with excellent performance at extremely low prices and with stable quality.

[0012] Furthermore, the electronic device should be usable or adaptable for a variety of purposes. More specifically, the performance of the electronic device should be maintained over a wide temperature range.

[0013] Surprisingly, it has been found that this objective is achieved through specific compounds described in more detail below, which are highly suitable for use in electroluminescent devices and result in organic electroluminescent devices exhibiting excellent performance, particularly in terms of lifetime, color purity, efficiency, operating voltage, and refractive index. Therefore, the present invention provides these compounds and electronic devices comprising these compounds, particularly organic electroluminescent devices.

[0014] This application provides a compound of formula (I),

[0015] Formula (I)

[0016] The Q group is selected from the structure of formula (Q-1).

[0017] Equation (Q-1)

[0018] The dashed bond represents a bond bonded to the L group, or, in the case of q=0, a bond bonded to the dibenzofuran-based skeleton of formula (I); s is 1, 2, or 3, preferably 1, wherein s is marked as 1 in the case of q=0; and other symbols are as follows: X is the same or different in each case and is N or CR. c Preferably, it is N, wherein at least one X group is N, and preferably both X groups are N; X a The same or different in each case and for N, CR a Or when the group combines with another group at that position, X a For C, X is preferred.a For CR a Or C, where each ring contains no more than two X's. a The group is N, preferably with no more than one X in each ring. a The group is N, more preferably all X a All groups are CR a Or C; X b The same or different in each case and for N, CR b Or when the group combines with another group at that position, X b For C, X is preferred. b For CR b Or C, where each ring contains no more than two X's. b The group is N, preferably with no more than one X in each ring. b The group is N, more preferably all X b All groups are CR b Or C; L may be the same or different in each case and is a combination of 6 to 40 aromatic ring atoms and in each case can be one or more non-H R atoms. d Divalent, trivalent, or tetravalent aromatic or heteroaromatic ring systems with substituted groups; q is 0 or 1, where q=0 means that the L group is absent and the Q group is directly bonded to the relevant atom of the dibenzofuran basic skeleton of formula (I), such as a carbon atom; R may be the same or different in each case and is a straight-chain alkyl, alkoxy, or thioalkoxy group having 1 to 10 carbon atoms or a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 10 carbon atoms, each of which may be one or more non-H R groups. 2 Group substitution, preferably R is a straight-chain alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, each of which can be replaced by one or more non-H R groups. 2 Group substitution; simultaneously, two or more preferably adjacent substituents R may form a ring; R a R b The same or different in each case and are H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar)2, N(R) c )2, C(=O)N(Ar)2, C(=O)N(R) c )2, C(Ar)3, C(R) c )3, Si(Ar)3, Si(R) c )3, Ge(Ar)3, Ge(R) c )3, B(Ar)2, B(R)c )2, C(=O)Ar, C(=O)R c , P(=O)(Ar)2, P(=O)(R c )2, P(Ar)2, P(R) c )2, S(=O)Ar, S(=O)R c S(=O)2Ar, S(=O)2R c OSO2Ar, OSO2R c A straight-chain alkyl, alkoxy, or thioalkoxy group having 1 to 40 carbon atoms, or an alkenyl or alkynyl group having 2 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 20 carbon atoms, wherein each of the alkyl, alkoxy, thioalkoxy, alkenyl, or alkynyl groups may be derived from one or more non-H R groups. c Group substitution, wherein one or more non-adjacent CH2 groups can be replaced by R c C=CR c C≡C, Si(R) c 2. C=O, C=S, C=Se, C=NR c -C(=O)O-, -C(=O)NR c -、NR c P(=O)(R) c (), -O-, -S-, SO or SO2, or have 5 to 60 aromatic ring atoms and in each case can be replaced by one or more non-H R c Aromatic or heteroaromatic ring systems with substituted groups, or having 5 to 60 aromatic ring atoms and being substituted by one or more R groups. c The aryloxy or heteroaryloxy group substituted by the radical; simultaneously, two R groups... a R b Groups together or one R a R b Group and another group (especially R) c (Groups) can also form rings; Ar may be the same or different in each case and is an R with 5 to 40 aromatic ring atoms and can be separated by one or more non-H atoms. c Aromatic or heteroaromatic ring systems with substituted groups, wherein Ar is preferably the same or different in each case and is an R having 6 to 20 aromatic ring atoms and being substituted by one or more non-H groups. c A group-substituted aryl or heteroaryl group, wherein if X is a CR c Then the Ar group can react with the R group of the X group. c The groups together form a ring; R c R dThe same or different in each case and are H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar')2, N(R) 1 )2,C(=O)N(Ar')2,C(=O)N(R 1 )2, C(Ar')3, C(R) 1 )3, Si(Ar')3, Si(R) 1 )3, Ge(Ar')3, Ge(R) 1 )3, B(Ar')2, B(R) 1 )2,C(=O)Ar',C(=O)R 1 ,P(=O)(Ar')2,P(=O)(R 1 )2, P(Ar')2, P(R) 1 )2,S(=O)Ar',S(=O)R 1 S(=O)2Ar', S(=O)2R 1 OSO2Ar', OSO2R 1 The alkyl, alkoxy, or thioalkoxy group having 1 to 40 carbon atoms, or an alkenyl or alkynyl group having 2 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 20 carbon atoms, wherein the alkyl, alkoxy, thioalkoxy, alkenyl, or alkynyl group in each case may be one or more non-H R 1 Group substitution, wherein one or more non-adjacent CH2 groups can be replaced by R 1 C=CR 1 C≡C, Si(R) 1 2. C=O, C=S, C=Se, C=NR 1 -C(=O)O-, -C(=O)NR 1 -、NR 1 P(=O)(R) 1 (), -O-, -S-, SO or SO2, or have 5 to 60 aromatic ring atoms and in each case can be replaced by one or more non-H R 1 Aromatic or heteroaromatic ring systems with substituted groups, or having 5 to 60 aromatic ring atoms and being substituted by one or more non-H R groups. 1 A group-substituted aryloxy or heteroaryloxy group; simultaneously, selected from R c R d Two groups together, or R c Or R d Group and another group (especially R) a Or R b (Groups) can also form rings; Ar' is the same or different in each case and is a group of 5 to 60 aromatic ring atoms that can be separated by one or more non-H R atoms. 1 Aromatic or heteroaromatic ring systems with substituted groups; wherein the two Ar' groups bonded to the same carbon, silicon, nitrogen, phosphorus, or boron atom can also be bonded by a single bond or selected from B(R) 1 ), C(R 1 )2、Si(R 1 2. C=O, C=NR 1 C=C(R) 1 )2、O、S、S=O、SO2、N(R 1 ), P(R 1 ) and P(=O)R 1 The bridges connect the bases of the bridges to each other; R 1 The same or different in each case and are H, D, F, Cl, Br, I, CN, NO2, N(Ar'')2, N(R) 2 )2,C(=O)Ar'',C(=O)R 2 ,P(=O)(Ar'')2,P(Ar'')2,B(Ar'')2,B(R 2 )2, C(Ar'')3, C(R) 2 )3, Si(Ar'')3, Si(R 2 )3, Ge(Ar'')3, Ge(R 2 3, a straight-chain alkyl, alkoxy, or thioalkoxy group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 40 carbon atoms, or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted with one or more non-H R 2 Group substitution, wherein one or more non-adjacent CH2 groups can be replaced by -R 2 C=CR 2 -、-C≡C-、Si(R 2 2. C=O, C=S, C=Se, C=NR 2 -C(=O)O-, -C(=O)NR 2 -、NR 2 P(=O)(R) 2 The atom is replaced by -O-, -S-, SO or SO2 and one or more of the hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or it has 5 to 60 aromatic ring atoms and in each case may be replaced by one or more R 2 Aromatic or heteroaromatic ring systems with substituted groups, or having 5 to 60 aromatic ring atoms and being substituted by one or more R groups. 2A group-substituted aryloxy or heteroaryloxy group, or a group having 5 to 60 aromatic ring atoms and being substituted by one or more non-H R groups. 2 Group-substituted aralkyl or heteroaralkyl groups, or combinations thereof; simultaneously, two or more preferably adjacent R groups 1 The groups together can form a ring, in which one or more R groups can form a ring. 1 The group can form a ring with another part of the compound; Ar'' is the same or different in each case and has 5 to 30 aromatic ring atoms and can be denoted by one or more R''. 2 Aromatic or heteroaromatic ring systems with substituted groups; wherein two Ar" groups bonded to the same carbon, silicon, nitrogen, phosphorus, or boron atom can also be bonded by a single bond or selected from B(R) 2 ), C(R 2 )2、Si(R 2 2. C=O, C=NR 2 C=C(R) 2 )2、O、S、S=O、SO2、N(R 2 ), P(R 2 ) and P(=O)R 2 The bridges connect the bases of the bridges to each other; R 2 In each case, the same or different aliphatic hydrocarbon groups selected from H, D, F, CN, having 1 to 20 carbon atoms, or aromatic or heteroaromatic ring systems having 5 to 30 aromatic ring atoms in which one or more hydrogen atoms can be replaced by D, F, Cl, Br, I, or CN, and said aromatic or heteroaromatic ring systems can be replaced by one or more alkyl groups each having 1 to 4 carbon atoms; at the same time, two or more preferably adjacent substituents R 2 Together they can form a ring.

[0019] In the context of this invention, an aryl group contains 6 to 40 carbon atoms; in the context of this invention, a heteroaryl group contains 3 to 40 carbon atoms and at least one heteroatom, provided that the sum of the carbon atoms and the heteroatom is at least 5. The heteroatom is preferably selected from N, O, and / or S. An aryl group or heteroaryl group herein refers to a simple aromatic ring, i.e., benzene, or a simple heteroaromatic ring, such as pyridine, pyrimidine, thiophene, etc., or a fused (enhanced) aryl or heteroaryl group, such as naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc. In contrast, aromatic compounds linked together by single bonds, such as biphenyl, are not referred to as aryl or heteroaryl groups, but rather as aromatic ring systems.

[0020] In the context of this invention, an aromatic ring system contains 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms. In the context of this invention, an aromatic ring system does not contain any heteroaryl groups. In the context of this invention, a heteroaromatic ring system contains 3 to 60 carbon atoms, preferably 3 to 40 carbon atoms, and at least one heteroaryl group, provided that the total number of carbon atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O, and / or S. In the context of this invention, an aromatic or heteroaromatic ring system should refer to a system that does not necessarily contain only aryl or heteroaryl groups, but in which two or more aryl or heteroaryl groups are also linked by non-aromatic units, such as carbon, nitrogen, or oxygen atoms. These should also refer to systems in which two or more aryl or heteroaryl groups are directly linked to each other, such as biphenyl, terphenyl, bipyridine, or phenylpyridine. For example, in the context of this invention, systems such as fluorene, 9,9'-spirodifluorene, 9,9-diarylfluorene, triarylamines, diaryl ethers, and stilbene should therefore also be considered aromatic ring systems, as are systems in which two or more aryl groups are linked, for example, by straight-chain or cyclic alkyl groups or by silyl groups. Preferred aromatic or heteroaromatic ring systems are simple aryl or heteroaromatic groups and groups in which two or more aryl or heteroaromatic groups are directly linked to each other, such as biphenyl, terphenyl, tetraphenyl, or bipyridine, and fluorene or spirodifluorene.

[0021] In the context of this invention, the aliphatic hydrocarbon group or alkyl group or alkenyl or ynyl group containing 1 to 20 carbon atoms, wherein some hydrogen atoms or CH2 groups may be replaced by the aforementioned groups, preferably refers to methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptenyl, or octyynyl groups. The alkoxy group having 1 to 40 carbon atoms is preferably alkoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexoxy, n-heptoxy, cycloheptoxy, n-octoxy, cyclooctoxy, 2-ethylhexoxy, pentafluoroethoxy, and 2,2,2-trifluoroethoxy. Thioalkyl groups having 1 to 40 carbon atoms, especially methyl thio, ethyl thio, n-propyl thio, isopropyl thio, n-butyl thio, isobutyl thio, sec-butyl thio, tert-butyl thio, n-pentyl thio, sec-butyl thio, n-hexyl thio, cyclohexyl thio, n-heptyl thio, cycloheptyl thio, n-octyl thio, cyclooctyl thio, 2-ethylhexyl thio, trifluoromethyl thio, pentafluoroethyl thio, 2,2,2-trifluoroethyl thio, ethylene thio, propylene thio, butene thio, pentene thio, cyclopentene thio, hexene thio, cyclohexene thio, hepten thio, cycloheptene thio, octenene thio, cyclooctenene thio, ethynyl thio, propynyl thio, butynyl thio, pentynyl thio, hexynyl thio, heptenyl thio, or octyynyl thio. Generally, the alkyl, alkoxy, or thioalkyl groups according to the present invention can be straight-chain, branched, or cyclic, wherein one or more non-adjacent CH2 groups can be replaced by the aforementioned groups; in addition, one or more hydrogen atoms can also be replaced by D, F, Cl, Br, I, CN, or NO2, preferably by F, Cl, or CN, more preferably by F or CN, and especially preferably by CN.

[0022] Aromatic or heteroaromatic ring systems having 5 to 60 or 5 to 40 aromatic ring atoms, which in each case can be substituted by the aforementioned groups and can be linked to the aromatic or heteroaromatic system via any desired position, are understood to particularly refer to groups derived from the following substances: benzene, naphthalene, anthracene, benzo[a]anthracene, phenanthrene, pyrene, oleanthracene, perylene, fluoranthracene, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, diphenylidene, terphenyl, terphenylidene, fluorene, spirodifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indo[a]fluorene, cis or trans indo[a]carbazole, cis or trans indol[a]carbazole. Trimeric indene, isomeric indene, spiromeric indene, spiroisomeric indene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenothiazine, pyrazole, indazole, imidazole, benzimidazole, naphthiazole, phenanthridine, pyridinium pyridimazole, pyrazinium pyridimazole, quinoxalineium pyridimazole, pyrazole, benzopyridine, naphthiazole Anthrazoazole, phenanthreneazole, isothrazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, hexaazatribenzide, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1,5-diazathracene, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperylene, pyrazine, phenazine, phenanthrene, phenothiazine, fluorescein ring, naphthidine, azacarbazole, benzocarbline, phenanthrene, 1,2,3-triazole, 1,2,4-triazole The group consisting of azoles, benzotriazoles, 1,2,3-thiadiazoles, 1,2,4-thiadiazoles, 1,2,5-thiadiazoles, 1,3,4-thiadiazoles, 1,2,3-thiadiazoles, 1,2,4-thiadiazoles, 1,2,5-thiadiazoles, 1,3,4-thiadiazoles, 1,3,5-triazines, 1,2,4-triazines, 1,2,3-triazines, tetrazolium, 1,2,4,5-tetraazines, 1,2,3,4-tetraazines, 1,2,3,5-tetraazines, purines, pteridines, indoleazines, and benzothiadiazoles, or groups derived from combinations of these systems.

[0023] In the context of this specification, the phrase "two or more groups may form a ring with each other" should be understood, in particular, to mean two groups connected to each other by chemical bonds, while formally eliminating two hydrogen atoms. This is illustrated by the following scheme: .

[0024] However, the above wording should also be understood to mean that if one of the two groups is hydrogen, the second group is attached to the position where the hydrogen atom is attached, thus forming a ring. This will be illustrated by the following scheme: .

[0025] In a preferred configuration, it is feasible for the compound to conform to formula (IIa), (IIb), (IIc), or (IId).

[0026] Equation (IIa) Equation (IIb)

[0027] Equation (IIc) Equation (IId)

[0028] The symbols R, Q, L, q, s, R a R b and R c It has the definition given above, especially for equation (I), and j is 2 or 3, i is 1 or 2, k is 0 or 1, where the sum of the two j is 5, the sum of the two i is 3, and the sum of j and k is 3.

[0029] In equation (IIa), the sum of the two labels j is 5, therefore -(L) q -(Q) s The group can be attached to the dibenzofuran-based skeleton with R a Group or R b The ring of the group. The same description applies to formula (IId), where the sum of the two i is 3.

[0030] Similarly, in equations (IIb) and (IIc), the sum of j and k is 3, such that -(L) q -(Q) s The group can be attached to the dibenzofuran-based skeleton with R a Group or R b The ring of the group.

[0031] In another preferred configuration, the feasible case is Equation-(L) q -(Q) s The Q group is selected from structures of formulas (Q-2) to (Q-16).

[0032] Equation (Q-2) Equation (Q-3) Equation (Q-4) Equation (Q-5)

[0033] Equation (Q-6) Equation (Q-7) Equation (Q-8) Equation (Q-9)

[0034] Equation (Q-10) Equation (Q-11) Equation (Q-12) Equation (Q-13)

[0035] Equation (Q-14) Equation (Q-15) Equation (Q-16)

[0036] The dashed bond represents a bond bonded to the L group, or, in the case of q=0, a bond bonded to the dibenzofuran-based skeleton of formula (I), denoted by R. c Ar has the definitions given above, especially for equation (I), and the other symbols are as follows: X c The same or different in each case and is N or CR c CR is preferred c Each ring contains no more than two X's. c The group is N, preferably with no more than one X in each ring. c The group is N, more preferably all X c All groups are CR c Or C; and Y c Selected from C(R) c )2、Si(R c )2、Ge(R c 2. NR c O or S, preferably NR c Or O, more preferably O.

[0037] Here, the structures of formula (Q-2), formula (Q-3) and formula (Q-11) are preferred, and the structure of formula (Q-2) is particularly preferred.

[0038] Another feasible configuration is that at least one Ar group from formulas (Q-1) to (Q-16), preferably both Ar groups, are selected from phenyl, biphenyl, terphenyl, tetraphenyl, fluorene, spirodifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, benzimidazole-benzimidazole, dibenzofuran, dibenzothiophene, indole-carbazole, indolo-carbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, or biphenylide, each of which can be substituted with one or more non-H R groups. cGroup substitution; preferably phenyl, biphenyl, fluorene, dibenzofuran, carbazole, biphenylide, indolocarbazole; more preferably phenyl, biphenyl, or dibenzofuran.

[0039] In a particularly preferred embodiment, the compounds of the present invention conform to one of the following formulas (III-1) to (III-27):

[0040] Equation (III-1) Equation (III-2)

[0041] Equation (III-3) Equation (III-4)

[0042] Equation (III-5) Equation (III-6)

[0043] Equation (III-7) Equation (III-8)

[0044] Equation (III-9) Equation (III-10)

[0045] Equation (III-11) Equation (III-12)

[0046] Equation (III-13) Equation (III-14)

[0047] Equation (III-15) Equation (III-16)

[0048] Equation (III-17) Equation (III-18)

[0049] Equation (III-19) Equation (III-20)

[0050] Equation (III-21) Equation (III-22)

[0051] Equation (III-23) Equation (III-24)

[0052] Equation (III-25) Equation (III-26)

[0053] Equation (III-27)

[0054] The symbols R, Q, L, q, s, R a R b and R c Having the definition given above, particularly for formula (I), and j being 2 or 3, wherein Q is preferably selected from the structure according to one of formulas (Q-2) to (Q-16), preferably one of formulas (Q-2), (Q-3), and (Q-11), and more preferably the structure of formula (Q-2). Here, the structures of formulas (III-2), (III-3), (III-8), (III-13), (III-14), (III-26), and (III-27) are preferred.

[0055] The diagram shown in the ring It refers to an R b Groups are bonded to each of the two unoccupied positions on the ring, where R b The functional groups may be the same or different in each case.

[0056] For similar diagrams, for example The corresponding definition applies, where R here is... d The group is bonded to the ring in question, and there are four unoccupied sites bonded to the group, which may be the same or different in each case.

[0057] Preferably, the L group is the same or different in each case and is selected from divalent, trivalent, or tetravalent phenyl, biphenyl, terphenyl, tetraphenyl, fluorene, spirodifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, benzimidazole-benzimidazole, dibenzofuran, dibenzothiophene, indole-carbazole, indolo-carbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, or biphenylide, each of which can be substituted with one or more non-H R groups. d Group substitution.

[0058] In a particularly preferred embodiment, it is feasible that in formulas (I), (IIa), (IIb), (IIc), (IId), or (III-1) to (III-27), the Q group conforms to formula (Q-2), s is labeled 1, and q is labeled 0, wherein at least one Ar group, preferably two Ar groups, in the formula are selected from phenyl, biphenyl, and dibenzofuran, and each of the groups can be substituted by one or more non-H R groups. c Group substitution.

[0059] In a more preferred embodiment, in formulas (I), (IIa), (IIb), (IIc), (IId), or (III-1) to (III-27), the Q group conforms to formula (Q-3), (Q-11), (Q-12), or (Q-13), denoted as s = 1, and denoted as q = 0, wherein at least one Ar group, preferably two Ar groups, in the formula are selected from phenyl, biphenyl, and dibenzofuran, and each of the groups can be converted by one or more non-H R groups. c Group substitution.

[0060] Another feasible scenario is that in formulas (I), (IIa), (IIb), (IIc), (IId), or (III-1) to (III-27), the Q group conforms to formula (Q-7), (Q-14), (Q-15), or (Q-16), denoted as s = 1, and denoted as q = 0, wherein at least one Ar group, preferably two Ar groups, in the formula are selected from phenyl, biphenyl, and dibenzofuran, and each of the groups can be converted by one or more non-H R groups. c Group substitution.

[0061] In a particularly preferred embodiment, it is feasible that in formulas (I), (IIa), (IIb), (IIc), (IId), or (III-1) to (III-27), the Q group conforms to formula (Q-2), s is labeled 1, and q is labeled 1, wherein the L group is selected from divalent phenyl, biphenyl, dibenzofuran, carbazole, and each of the groups can be substituted by one or more non-H R groups. d Group substitution, wherein at least one Ar group, preferably both Ar groups, are selected from phenyl, biphenyl, and dibenzofuran, and each group may be substituted with one or more non-H R groups. c Group substitution.

[0062] In a more preferred embodiment, in formulas (I), (IIa), (IIb), (IIc), (IId), or (III-1) to (III-27), the Q group conforms to formula (Q-3), (Q-11), (Q-12), or (Q-13), denoted as 1, and denoted as 1, wherein the L group is selected from divalent phenyl, biphenyl, dibenzofuran, and carbazole, and each of the groups can be substituted by one or more non-H R groups. d Group substitution, wherein at least one Ar group, preferably both Ar groups, are selected from phenyl, biphenyl, and dibenzofuran, and each group may be substituted with one or more non-H R groups. c Group substitution.

[0063] Another feasible scenario is that in formulas (I), (IIa), (IIb), (IIc), (IId), or (III-1) to (III-27), the Q group conforms to formula (Q-7), (Q-14), (Q-15), or (Q-16), denoted as 1, and q denoted as 1, wherein the L group is selected from divalent phenyl, biphenyl, dibenzofuran, and carbazole, and each of the groups can be substituted by one or more non-H R groups. d Group substitution, wherein at least one Ar group, preferably both Ar groups, are selected from phenyl, biphenyl, and dibenzofuran, and each group may be substituted with one or more non-H R groups. c Group substitution.

[0064] Another feasible scenario is equation -(L). q -(Q) s -(L) in q -Group representation-(L d ) o The structure is -, hence -(L) q -(Q) s The groups in the formula are selected from -(L d ) o -(Q) s The structure, where o is marked as 0, 1, 2, 3, 4 or 5, where o=0 means L d The group is absent and the Q group is directly bonded to the relevant atom of the dibenzofuran-based skeleton of formula (I), such as a carbon atom, wherein o is preferably 0, 1 or 2, more preferably 0 or 1, and L d The group is selected from formula (L d -1) to formula (L) d The structure of -13):

[0065] The dashed key indicates the connection point, and the other symbols are as follows: Xd The same or different in each case and for N, CR d Or when the group combines with another group at that position, X d For C, X is preferred. d For CR d Or C, where each ring contains no more than three X's. d The group is N, preferably with no more than two X groups in each ring. d The group is N, more preferably all X d All groups are CR d Or C, where R d It has the definition given above, especially for equation (I); Y d Selected from C(R) d 2. NR d O or S, NR is preferred. d Or O, more preferably NR d ; Wherein the formula -(L d ) o The structure of - is in the formula -(L d ) o -(Q) s The label in the symbol is divalent when s=1, trivalent when s=2, and tetravalent when s=3.

[0066] In this preferred formula (L) d -1), Equation (L) d -2), Equation (L) d -4) and formula (L) d The structure of -6), particularly preferred formula (L) d -1) and formula (L) d -2) structure.

[0067] In a preferred configuration, L d The group is selected from formula (L d -14) to formula (L) d The structure of -33):

[0068] The dashed key represents a connection site, symbol R. d With the definition given above, especially for equation (I), the symbol X d With the above, especially the targeted (L) d -1) to formula (L) d-13) is the definition given, and the other symbols are as follows: i is 1 or 2; and j is 0, 1, or 2.

[0069] In this preferred formula (L) d -14), Formula (L) d -16), Formula (L) d -17), Formula (L) d -19), Formula (L) d -20) and formula (L) d The structure of -24), particularly preferred formula (L) d -14), Formula (L) d -16) and formula (L) d The structure of -17).

[0070] In a particularly preferred embodiment, it is feasible that in formulas (I), (IIa), (IIb), (IIc), (IId), or (III-1) to (III-27), the Q group conforms to formula (Q-2), the label s is 1, and the label o is 1, wherein L d The group is selected from formula (L d -1), Equation (L) d -4), Formula (L) d -5), Formula (L) d -6), Formula (L) d -14), Formula (L) d -15), formula (L) d -16), Formula (L) d -20), formula (L) d The structure of -21) wherein at least one Ar group, preferably two Ar groups, is selected from phenyl, biphenyl, and dibenzofuran, and each group can be converted by one or more non-H R groups. c Group substitution.

[0071] In a more preferred embodiment, in formulas (I), (IIa), (IIb), (IIc), (IId), or (III-1) to (III-27), the Q group conforms to formula (Q-3), (Q-11), (Q-12), or (Q-13), the designation s is 1, and the designation o is 1, wherein L d The group is selected from formula (L d -1), Equation (L) d -4), Formula (L) d -5), Formula (L) d -6), Formula (L) d -14), Formula (L) d -15), formula (L) d -16), Formula (L)d -20), formula (L) d The structure of -21) wherein at least one Ar group, preferably two Ar groups, is selected from phenyl, biphenyl, and dibenzofuran, and each group can be converted by one or more non-H R groups. c Group substitution.

[0072] Another feasible scenario is that in formulas (I), (IIa), (IIb), (IIc), (IId), or (III-1) to (III-27), the Q group conforms to formula (Q-7), (Q-14), (Q-15), or (Q-16), with s being 1 and o being 1, where L d The group is selected from formula (L d -1), Equation (L) d -4), Formula (L) d -5), Formula (L) d -6), Formula (L) d -14), Formula (L) d -15), formula (L) d -16), Formula (L) d -20), formula (L) d The structure of -21) wherein at least one Ar group, preferably two Ar groups, is selected from phenyl, biphenyl, and dibenzofuran, and each group can be converted by one or more non-H R groups. c Group substitution.

[0073] In a preferred embodiment, the compounds of the present invention conform to one of the following formulas (IV-1) to (IV-4):

[0074] Formula (IV-1) Formula (IV-2) Formula (IV-3)

[0075] Formula (IV-4)

[0076] The symbols R, X, X a X b Ar has the definition given above, especially for equation (I), and the symbol X d and Y d With the above, especially the targeted (L) d -1) to formula (L) d -13) gives the definition. Here, the structures of equations (IV-1) and (IV-2) are preferred.

[0077] Another feasible scenario is, especially in equations (IV-1) to (IV-4), where there are no more than two X's in each ring. a X b X d The group is N, preferably all X a X b X d All groups are CR a CR b CR d Groups, preferably at least one, more preferably at least two X groups in each ring. a X b X d The radical group is selected from CH and CD.

[0078] Furthermore, particularly in equations (IV-1) to (IV-4), it is feasible to have no more than four, and preferably no more than two, X. a X b X d The group is N, more preferably all X a X b X d All groups are CR a CR b CR d Groups, wherein preferably no more than 4, more preferably no more than 3, and particularly preferably no more than 2 are derived from X a X b X d CR a CR b CR d The group is not a CH or CD group.

[0079] In a particularly preferred embodiment, the compounds of the present invention conform to one of the following formulas (V-1) to (V-37):

[0080] Equation (V-1) Equation (V-2) Equation (V-3)

[0081] Equation (V-4) Equation (V-5) Equation (V-6)

[0082] Equation (V-7) Equation (V-8) Equation (V-9)

[0083] Equation (V-10) Equation (V-11) Equation (V-12)

[0084] Equation (V-13) Equation (V-14) Equation (V-15)

[0085] Equation (V-16) Equation (V-17) Equation (V-18)

[0086] Equation (V-19) Equation (V-20) Equation (V-21)

[0087] Equation (V-22) Equation (V-23) Equation (V-24)

[0088] Equation (V-25) Equation (V-26) Equation (V-27)

[0089] Equation (V-28) Equation (V-29) Equation (V-30)

[0090] Equation (V-31) Equation (V-32) Equation (V-33)

[0091] Equation (V-34) Equation (V-35) Equation (V-36)

[0092] Equation (V-37)

[0093] Among them, the symbols R and R a Rb R c R d And Ar has the definition given above, especially for equation (I), with the symbol Y d With the above, especially the targeted (L) d -1) to formula (L) d -13) is the definition given, and the other symbols are as follows: n is 2 or 3.

[0094] In particular, it is also feasible to have no more than five, preferably no more than four, and more preferably no more than three R values ​​in equations (V-1) to (V-37). a R b R c R d The radical is not H or D.

[0095] The structures of formulas (V-1), (V-2), (V-4), (V-9), (V-10), (V-13), (V-14), (V-17), (V-18), (V-33), (V-34), and (V-37) are preferred here, and the structures of formulas (V-1), (V-2), (V-4), (V-33), and (V-37) are particularly preferred.

[0096] Another feasible scenario is that at least one R a Or R b The group corresponds to formula -(L) q -(Q) s The group, wherein L and Q have the definitions given above, especially with respect to formula (I), wherein Q is preferably selected from the structures of formulas (Q-2) to (Q-16), q is 0 or 1, s is 1, 2 or 3, preferably 1 or 2, wherein preferably only one R a Or R b The group corresponds to formula -(L) q -(Q) s The group. Having exactly one formula -(L) q -(Q) s Compounds with the group -(L) are preferred to have two or three -(L) groups. q -(Q) s Compounds with an R group, the latter class of compounds is characterized by an R group. a Or R b The group corresponds to formula -(L) q -(Q) s . group.

[0097] Another feasible scenario is at least one R a Or R b The group corresponds to the formula -(Ld ) o -(Q) s The group Q has the definition described above, especially with respect to formula (I), and is preferably selected from the structures of formulas (Q-2) to (Q-16), the notation o is 0, 1, 2, 3, 4 or 5, preferably 0, 1 or 2, more preferably 0 or 1, the notation s is 1, 2 or 3, preferably 1 or 2, L d The group is selected from formula (L d -1) to formula (L) d -33) structures, wherein these structures are as described above, wherein preferably exactly one R a Or R b The group corresponds to the formula -(L d ) o -(Q) s The group. Having exactly one of the formula -(L d ) o -(Q) s Compounds with the group of -(L) are preferred to have two or three -(L) groups. d ) o -(Q) s Compounds with an R group, the latter class of compounds is characterized by an R group. a Or R b The group corresponds to the formula -(L d ) o -(Q) s . group.

[0098] The preferred case is at least one R a Or R b The group corresponds to the group of formula C(R)3, where R has the definition given above, especially with respect to formula (I), wherein preferably there is exactly one or exactly two R. a Or R b The group corresponds to a group of formula C(R)3. Compounds having exactly three groups of formula C(R)3 are preferred over compounds having exactly two groups of formula C(R)3. These preferred compounds are characterized by having at least one R group. a Or R b The group corresponds to the group in formula C(R)3.

[0099] The preferred case is at least one R a Or R b The group is an aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, preferably selected from phenyl, biphenyl, terphenyl, fluorene, spirofluorene, dibenzofuran, and more preferably phenyl. Each of the groups can be generated by one or more R... cGroup substitution is preferred, but more preferably, no substitution is made except for D. In this case, the aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms is more preferably selected from the structures (Ar-1) to (Ar-3) and (Ar-13) to (Ar-16) described later. Preferably, exactly one or two of the groups R are present. a Or R b Compounds are aromatic or heteroaromatic ring systems having 6 to 18 aromatic ring atoms.

[0100] In one embodiment, it is feasible for the Q group not to contain a carbazole group, and preferably not to contain any hole transport group.

[0101] In one embodiment, it is feasible for the L group not to contain a carbazole group, and preferably not to contain any hole transport group.

[0102] Compounds in which the L and / or Q groups do not contain any hole transport groups are particularly suitable as electron injection materials, electron transport materials or hole blocking materials for use in the corresponding layers, wherein the layers typically do not contain any luminescent compounds.

[0103] In another embodiment, it is feasible for the Q group to include a hole transport group, preferably a carbazole group.

[0104] In another embodiment, it is feasible for the L group to contain a hole transport group, preferably a carbazole group.

[0105] Compounds containing electron transport groups in the L and / or Q groups are particularly suitable as host materials for use in combination with luminescent compounds.

[0106] Hole transport groups are well-known in the field. These include, in particular, carbazole groups and groups with similar properties.

[0107] In a preferred embodiment, the feasible case is R a R b R c R d The group does not contain any aromatic or heteroaromatic ring system having three linearly fused aromatic 6-membered rings, wherein R is preferred. a R b R c R d None of the groups contain aromatic or heteroaromatic ring systems with three linearly fused aromatic 6-membered rings.

[0108] A more preferable case is R a R b R c R d The group does not contain any aromatic or heteroaromatic ring system having three mutually fused aromatic 6-membered rings, wherein R is preferred.a R b R c R d None of the groups contain aromatic or heteroaromatic ring systems with three mutually fused aromatic 6-membered rings.

[0109] Another feasible scenario is that the compound does not contain any aromatic or heteroaromatic ring system having three mutually fused aromatic 6-membered rings.

[0110] In a preferred embodiment of the present invention, it is feasible to have at least two preferably adjacent R a R b R c R d Groups and these two R a R b R c R d The other groups bonded to the group together form a fused ring. In a preferred configuration, it is feasible to form the ring structure described in document WO 2022 / 079068 A1, filed October 13, 2021, with European Patent Application No. PCT / EP2021 / 078240, filed with the European Patent Office; for the purposes of this disclosure, the description of the fused ring structure shown in these documents and on pages 37 to 40 of document WO2022 / 079068 A1, of the ring elements of formulas (RA-1) to (RA-12), (RA-1a) to (RA-4f), and / or (RB), is incorporated herein by reference. The ring structure detailed above in document WO 2022 / 079068 A1, and preferably comprising the ring elements of formulas (RA-1) to (RA-12) and (RA-1a) to (RA-4f), particularly results in the compounds of the present invention having a surprisingly low refractive index.

[0111] Another feasible scenario is based on the substituent R in the above formula. a R b R c R d and R 1 Without substituent R a R b R c R d and R 1 The ring atoms of the combined ring system form a fused aromatic or heteroaromatic ring system. This includes the formation of a fused aromatic or heteroaromatic ring system in which a feasible substituent R... 1 and R 2 Can be combined with substituent R a R b R c R d and R 1Bonding.

[0112] When the compounds of the present invention are reacted with aromatic or heteroaromatic R a R b R c R d R 1 Or R 2 When substituting groups, it is preferable that these groups do not have any aryl or heteroaryl groups consisting of more than two directly fused aromatic six-membered rings. More preferably, the substituents do not have any aryl or heteroaryl groups consisting of six-membered rings directly fused to each other. This preference is due to the low triplet energy of these structures. Fused aryl groups having more than two directly fused aromatic six-membered rings but still suitable according to the invention are phenanthrene and biphenylide, because these also have high triplet energy levels.

[0113] Preferably, -(L) q -(Q) s The group or Q group may be combined with formula (I) or the preferred embodiment of the formula -(L). q -(Q) s The dibenzofuran groups bonded by the groups form complete conjugation. A direct bond between adjacent aromatic or heteroaromatic rings forms a complete conjugated aromatic or heteroaromatic system. Another bond between the aforementioned conjugated groups, such as a bond via a sulfur, nitrogen, or oxygen atom or a carbonyl group, does not negatively affect the conjugation.

[0114] When it is specifically selectable from R, R a R b R c R d R 1 and / or R 2 When two groups together form a ring, the ring can be monocyclic or polycyclic, aliphatic, or heteroaliphatic, and in R... a R b R c R d R 1 and / or R 2 In the case of substituents, the groups can be aromatic or heteroaromatic. In this case, the groups forming the ring together can be adjacent, meaning these groups are bonded to the same carbon atom or to carbon atoms directly bonded to each other, or they can be far apart from each other. Furthermore, the presence of substituents R... c R d R 1 and / or R 2 The ring systems can also be connected to each other via bonds, thus enabling ring closure.

[0115] Another feasible scenario is at least one R a Rb R c R d The groups may be the same or different in each case and are selected from aromatic or heteroaromatic ring systems, which are selected from the following formulas Ar-1 to Ar-76, and / or the Ar' groups may be the same or different in each case and are selected from the following formulas Ar-1 to Ar-76:

[0116] Where R 1 As defined above, a dashed bond represents a bond bonded to the corresponding group. Furthermore: Ar 1The same or different in each case and having 6 to 18 aromatic ring atoms and in each case can be one or more R 1 Divalent aromatic or heteroaromatic ring systems with substituted groups; A is the same or different in every case and is C(R) 1 2. NR 1 , O or S; p is either 0 or 1, where p=0 means Ar 1 The functional group is absent and the corresponding aromatic or heteroaromatic functional group is directly bonded to the corresponding functional group; q is 0 or 1, where q=0 means that there is no A group bonded to that position, but rather R. 1 The functional group is bonded to the corresponding carbon atom.

[0117] The structures of equations (Ar-1) to (Ar-76) detailed above are, for example, R defined in the structure of equation (I). a Or R b The preferred configuration of the group, in this case, is that the substituent R in formulas (Ar-1) to (Ar-76) is... 1 Should be R c Instead, where R c It has the definition described above, especially for formula (I).

[0118] Furthermore, the structures of formulas (Ar-1) to (Ar-76) detailed above are preferred configurations of the Ar group as defined in, for example, the structure of formula (I), in which case the substituent R in formulas (Ar-1) to (Ar-76) 1 Should be R c Instead, where R c It has the definition described above, especially for formula (I).

[0119] The preferred structures are those of Ar-1, Ar-2, Ar-3, Ar-12, Ar-13, Ar-14, Ar-15, Ar-16, Ar-40, Ar-41, Ar-42, Ar-43, Ar-44, Ar-45, Ar-46, Ar-69, Ar-70, and Ar-76, and the structures of Ar-1, Ar-2, Ar-3, Ar-12, Ar-13, Ar-14, Ar-15, and Ar-16 are particularly preferred.

[0120] When the structures of formulas (Ar-1) to (Ar-76) have two or more A groups, feasible options for these groups include all combinations derived from the definition of A. In this case, a preferred embodiment is that one of the A groups is NR. 1 And the other A group is C(R) 1 )2 or both of the A groups are NR 1 Or those in which both A groups are O.

[0121] When A is NR 1 When the substituent R bonded to the nitrogen atom 1 Preferably, it has 5 to 24 aromatic ring atoms and can be further divided by one or more R 2 Aromatic or heteroaromatic ring systems with substituted groups. In a particularly preferred embodiment, the R... 1 The substituents may be the same or different in each case and are of 6 to 24 aromatic ring atoms, especially 6 to 18 aromatic ring atoms, and in each case may be replaced by one or more R. 2 A group-substituted aromatic or heteroaromatic ring system, wherein the aromatic or heteroaromatic ring system does not have any fused aryl group and any fused heteroaromatic group in which two or more aromatic or heteroaromatic 6-membered ring groups are directly fused to each other. Phenyl, biphenyl, terphenyl, and tetraphenyl are preferred. Also preferred are triazine, pyrimidine, and quinazoline as listed above for Ar-47 to Ar-50, Ar-57, and Ar-58, wherein these structures can be substituted by one or more R 2 Group substitution, rather than being R 1 replace.

[0122] When A is C(R) 1 When )2, the substituent R bonded to this carbon atom 1 Preferably, in each case, the same or different, and is a straight-chain alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, said group or ring system may also be composed of one or more R 2 Group substitution. Most preferably, R 1 It is a methyl group or a phenyl group. In this case, R 1 The groups can also form ring systems together, thus obtaining spirocyclic systems.

[0123] The preferred substituent R is described below. a R b R c and R d .

[0124] In a preferred embodiment of the present invention, R a R bThe same or different in each case and selected from H, D, F, CN, NO2, Si(R) c 3, B(OR) c )2, a straight-chain alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, wherein the alkyl group in each case may be one or more R 1 Group substitution, or having 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, and in each case may be substituted with one or more R groups. c Aromatic or heteroaromatic ring systems with substituted groups.

[0125] In a preferred embodiment of the present invention, R c R d The same or different in each case and selected from H, D, F, CN, NO2, Si(R) 1 3, B(OR) 1 )2, a straight-chain alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, wherein the alkyl group in each case may be one or more R 1 Group substitution, or having 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, and in each case may be substituted with one or more R groups. 1 Aromatic or heteroaromatic ring systems with substituted groups.

[0126] In another preferred embodiment of the invention, the substituent R a R b R c R d In each case, the same or different alkyl groups selected from H, D, F, are straight-chain alkyl groups having 1 to 20 carbon atoms or branched or cyclic alkyl groups having 3 to 20 carbon atoms, wherein the alkyl groups in each case may be one or more R 1 The group is substituted, or it has 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, and in each case it can be replaced by one or more non-H R groups. c Or R 1 Aromatic or heteroaromatic ring systems with substituted groups.

[0127] Another feasible scenario is at least one R a R b R c R d Group, preferably substituent R a R b R c R dIn each case, they may be the same or different and are selected from H, D, or have 6 to 30 aromatic ring atoms and can be derived from one or more R atoms. 1 Aromatic or heteroaromatic ring systems substituted with groups. More preferably, at least one substituent R c R d In each case, they may be the same or different and are selected from R atoms having 6 to 30 aromatic ring atoms and being capable of being separated by one or more non-H atoms. c Or R 1 Aromatic or heteroaromatic ring systems with substituted groups.

[0128] More preferably, R a R b R c R d The groups may be the same or different in each case and are selected from H, D, or aromatic or heteroaromatic ring systems having 6 to 24 aromatic ring atoms, preferably 6 to 18 aromatic ring atoms, more preferably 6 to 13 aromatic ring atoms, each of which can be converted by one or more non-H R groups. c Or R 1 Group substitution.

[0129] Another feasible scenario is at least one R a R b R c R d The group is an aromatic ring with 5 to 13 atoms and can be bonded by one or more non-H R atoms. c Or R 1 Aromatic or heteroaromatic ring systems with substituted groups.

[0130] Preferably, at least one group, preferably a substituent R a R b R c R d In each case, the groups may be the same or different and selected from phenyl, biphenyl, terphenyl, tetraphenyl, fluorene, spirofluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indole-carbazole, indolo-carbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, or biphenylide, each of which may be substituted with one or more non-H R groups. c Or R 1 Group substitution. The term "substituent" here specifically refers to R. a R b R c R d Not H. Furthermore, if two or more substituents selected from the aforementioned aromatic or heteroaromatic groups are present, then the substituent R... a R b R c Rd They can be the same or different.

[0131] Another feasible scenario is that the R groups bonded to a carbon atom are identical.

[0132] Another possible scenario is that the R groups bonded to different carbon atoms are the same.

[0133] Another feasible scenario is that the R groups bonded to different carbon atoms are different.

[0134] Preferably, the R group bonded to the carbon atom is selected from a straight-chain alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, each of which can be bonded to one or more R groups. 2 The substituents are preferably deuterated, wherein two or more substituents R can form a ring together.

[0135] Preferably, the R group is methyl, ethyl, or propyl, or three R groups bonded to the same carbon atom form a bicyclic alkyl or tricyclic alkyl group having 9 or 10, preferably 9, carbon atoms, wherein the R group is preferably methyl, and these groups may be deuterated.

[0136] By substituent R a R b R c R d Or R 1 The preferred aromatic or heteroaromatic ring system represented by Ar or Ar' is selected from phenyl, biphenyl (especially ortho-, meta-, or para-biphenyl), terphenyl (especially ortho-, meta-, or para-terphenyl or branched terphenyl), tetraphenyl (especially ortho-, meta-, or para-terphenyl or branched tetraphenyl), fluorene that can be linked via the 1, 2, 3, or 4 positions, spirodifluorene that can be linked via the 1, 2, 3, or 4 positions, and naphthalene (especially the 1 or 2 position bond). Naphthalene, indole, benzofuran, benzothiophene, carbazole linked at positions 1, 2, 3, or 4, dibenzofuran linked at positions 1, 2, 3, or 4, dibenzothiophene linked at positions 1, 2, 3, or 4, indocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, anthracene, pyrene, perylene, leucovorin, phenanthrene, or biphenylide, each of the ring systems being soluble in one or more R... c R 1 Or R 2Group substitution. Structures Ar-1 to Ar-76 listed above are particularly preferred, especially those of formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16), (Ar-69), (Ar-70), and (Ar-76), with particular preference for structures of formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), and (Ar-16). Regarding structures Ar-1 to Ar-76, it should be noted that these structures are shown to have substituents R. 1 In the ring system Ar and R a R b In the case of groups, these substituents R 1 Should be R c Instead, and in R 1 In the case of a group, it should be R 2 replace.

[0137] In another preferred embodiment of the invention, R 1 In each case, the same or different alkyl groups selected from H, D, F, CN, having 1 to 10 carbon atoms, are straight-chain alkyl groups or branched or cyclic alkyl groups having 3 to 10 carbon atoms, wherein the alkyl group in each case may be one or more R 2 Group substitution, or having 6 to 24 aromatic ring atoms and in each case being substituted with one or more R groups. 2 Aromatic or heteroaromatic ring systems with substituted groups. In a particularly preferred embodiment of the invention, R 1 In each case, the same or different and selected from H, are straight-chain alkyl groups having 1 to 6 carbon atoms, especially having 1, 2, 3, or 4 carbon atoms, or are branched or cyclic alkyl groups having 3 to 6 carbon atoms, wherein the alkyl group may be one or more R 2 The group is substituted, but preferably unsubstituted, or has 6 to 13 aromatic ring atoms and in each case can be substituted by one or more R groups. 2 Aromatic or heteroaromatic ring systems that are substituted with groups, but preferably unsubstituted.

[0138] In another preferred embodiment of the invention, R 2 In each case, the same or different and of the same type, is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms, said group may be substituted with an alkyl group having 1 to 4 carbon atoms, but preferably not substituted.

[0139] Furthermore, in the compounds of the present invention processed by vacuum evaporation, the alkyl group preferably has no more than five carbon atoms, more preferably no more than four carbon atoms, and most preferably no more than one carbon atom. For compounds processed from solution, suitable compounds also include those substituted with alkyl groups having up to 10 carbon atoms (especially branched alkyl groups), or those substituted with oligomeric aromatic groups (e.g., o-terphenyl, m-terphenyl, or p-terphenyl, or branched terphenyl, or tetraphenyl group).

[0140] In a preferred embodiment, the compound is at least 50%, particularly at least 80%, and more preferably completely (100%) deuterated. This means that in such compounds, the corresponding proportion of hydrogen atoms present in the undeuterated compound has been exchanged for D. The undeuterated compound is the corresponding compound in which deuterium is exchanged for hydrogen and therefore does not contain D. In the completely deuterated compound, all H atoms are exchanged for D.

[0141] In a preferred embodiment, some portions of the compound are completely undeuterated, while others are mostly or completely deuterated. In a preferred embodiment, the Q group or the Q group and L group may be mostly or completely deuterated, and the other portions of the compound of formula (I) are completely undeuterated. In an alternative preferred embodiment of the invention, the Q group or the Q group and L group are completely undeuterated, and the remaining groups of the compound of formula (I) are mostly or completely deuterated.

[0142] When the compound of formula (I) or a preferred embodiment is used as a matrix material for a phosphorescent emitter or in a layer directly adjacent to the phosphorescent layer, it is more preferable that the compound does not contain any fused aryl or heteroaryl groups in which more than two six-membered rings are directly fused together. An exception to this case is formed by phenanthrene and biphenylide, which, despite the presence of fused aromatic six-membered rings, are still preferred due to their high triplet energy.

[0143] Preferably, the molecular weight of the compound of the present invention is not more than 5000 g / mol, more preferably not more than 4000 g / mol, particularly preferably not more than 3000 g / mol, especially preferably not more than 2000 g / mol, even more preferably not more than 1200 g / mol, and most preferably not more than 900 g / mol.

[0144] Furthermore, the preferred compounds of the present invention are characterized in that they are sublimable. The molar mass of these compounds is typically less than about 1200 g / mol.

[0145] Preferably, the compound does not contain any alkoxy, thioalkoxy, or hydroxy groups.

[0146] Another feasible scenario is that the compound of formula (I) or a preferred embodiment of the compound does not come into direct contact with metal atoms, and is preferably not a ligand of a metal complex.

[0147] The preferred embodiments described above can be combined with each other as needed within the limitations defined in claim 1. In a particularly preferred embodiment of the invention, all of the above-mentioned preferences are present simultaneously.

[0148] Examples of preferred compounds according to the embodiments detailed above are the compounds detailed in the table below.

[0149]

[0150] The basic structures of the compounds of this invention can be prepared via the routes outlined below. The individual synthetic steps described herein, such as coupling reactions leading to C / C bond formation and / or CN bond formation, are known in principle to those skilled in the art. These include the Buchwald reaction, Suzuki reaction, Yamamoto reaction, Stieler reaction, Heck reaction, Negishi reaction, sage reaction, and hibiscus reaction.

[0151] More information on the synthesis of the compounds of this invention can be found in the synthesis examples.

[0152] The following scheme describes the preparation of the compounds of the present invention using specific dibenzofuran compounds. This use should be considered exemplary, and other compounds of the present invention can be obtained through similar synthetic routes starting from different basic structures.

[0153] Wherein L is an aromatic or heteroaromatic ring system of the present invention compound (3), which can be prepared from trifluoromethanesulfonate or halogen-functionalized 4,X-ditert-alkyl-substituted dibenzofuran (1) known in the literature, together with boric acid or ester (2) known in the literature, in the presence of a base, palladium compound, phosphine and solvent or solvent mixture, by CC coupling method known to those skilled in the art (preferably Suzuki coupling); see Scheme 1.

[0154] Option 1:

[0155] The compound (6) of the present invention, which is directly linked to a heterocyclic compound (5) and a dibenzofuran, can be prepared from a functionalized 4,X-ditert-alkyl-substituted dibenzofuran borate or ester (4) known in the literature, by a CC coupling method known to those skilled in the art (preferably Suzuki coupling), in the presence of a base, a palladium compound, a phosphine and a solvent or a mixture of solvents; see Scheme 2.

[0156] Option 2:

[0157] Schemes (1) and (2) should be considered exemplary, and therefore other RG groups are also applicable, as shown in the examples.

[0158] The definitions of the symbols used in the above scheme basically correspond to the definitions given for equation (I). For clarity, the numbers and full representations of all symbols are omitted.

[0159] Therefore, the present invention also provides a method for preparing the compounds of the present invention, wherein a dibenzofuran compound is synthesized and at least one nitrogen-containing heteroaromatic group is introduced, preferably by means of a nucleophilic aromatic substitution reaction or a coupling reaction.

[0160] These methods, followed by purification if necessary, such as recrystallization or sublimation, can yield compounds of the present invention with high purity, preferably greater than 99% (determined by 1H NMR and / or HPLC).

[0161] The compounds of the present invention can also be mixed with polymers. Similarly, these compounds can be covalently incorporated into polymers. This is particularly feasible in the case of compounds substituted with reactive leaving groups such as bromine, iodine, chlorine, boric acid, or borate esters, or substituted with reactive polymerizable groups such as olefins or oxetanes. These can be used as monomers for the manufacture of the corresponding oligomers, dendritic macromolecules, or polymers. Oligopolymerization or polymerization is preferably achieved via halogen functional groups or boric acid functional groups or via polymerizable groups. Furthermore, polymers can be crosslinked via such groups. The compounds and polymers of the present invention can be used in the form of crosslinked or uncrosslinked layers.

[0162] Therefore, the present invention also provides oligomers, polymers, or dendritic macromolecules containing one or more of the structures of formula (I) detailed above and preferred embodiments of that formula, or compounds of the present invention, wherein one or more bonds are present between the compounds of the present invention or the structures of formula (I) and preferred embodiments of that formula and the polymer, oligomer, or dendritic macromolecule. According to the connection of the structures of formula (I) and preferred embodiments of that formula, or the compounds, these thus form side chains of the oligomer or polymer or are bonded within the main chain. The polymer, oligomer, or dendritic macromolecule may be conjugated, partially conjugated, or non-conjugated. The oligomer or polymer may be linear, branched, or dendritic. The same preferences as described above apply to the repeating units of the compounds of the present invention in the oligomers, dendritic macromolecules, and polymers.

[0163] To prepare the oligomers or polymers, the monomers of the present invention are homopolymerized or copolymerized with other monomers. Preferably, copolymers are used in which the units of formula (I) or the preferred embodiments described in the context are present in the range of 0.01 mol% to 99.9 mol%, preferably 5 mol% to 90 mol%, more preferably 20 mol% to 80 mol%. Suitable and preferred comonomers forming the basic polymer backbone are selected from fluorene (e.g., according to EP 842208 or WO 2000 / 022026), spirodifluorene (e.g., according to EP707020, EP 894107 or WO 2006 / 061181), p-phenylene (e.g., according to WO 92 / 18552), carbazole (e.g., according to WO 2004 / 070772 or WO 2004 / 113468), thiophene (e.g., according to EP 1028136), dihydrophenanthrene (e.g., according to WO2005 / 014689), cis and trans-indenofluorene (e.g., according to WO 2004 / 041901 or WO 2004 / 113412), ketones (e.g., according to WO 2005 / 040302), and phenanthrene (e.g., according to WO 2005 / 104264 or WO (2007 / 017066) or a variety of these units. The polymers, oligomers and dendritic macromolecules may also contain other units, such as hole transport units, especially those based on triarylamines, and / or electron transport units.

[0164] In particular, the compounds of the present invention characterized by high glass transition temperatures are of particular interest. In this regard, compounds of the present invention comprising the structure of formula (I) or the preferred embodiments described in the context are especially preferred, having a glass transition temperature of at least 70°C, more preferably at least 110°C, even more preferably at least 125°C, and especially preferably at least 150°C, as determined according to DIN 51005 (2005-08 edition).

[0165] In order to process the compounds of the present invention from the liquid phase, for example by spin coating or printing, formulations of the compounds of the present invention are required. These formulations may be, for example, solutions, dispersions, or emulsions. For this purpose, a mixture of two or more solvents may be preferred. Suitable and preferred solvents include, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, naphthalene, o-dimethoxybenzene, THF, methyl-THF, THP, chlorobenzene, dimethylbenzene, phenoxytoluene (especially 3-phenoxytoluene), (-)-fenazine, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methyl anisole, 4-methyl anisole, 3,4-dimethyl anisole, 3,5-dimethyl anisole, acetophenone, α-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, and cyclohexanol. Hexanone, cyclohexylbenzene, decahydronaphthalene, dodecylbenzene, ethyl benzoate, indane, NMP, p-cymene, phenethyl ether, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, 2-methylbiphenyl, 3-methylbiphenyl, 1-methylnaphthalene, 1-ethylnaphthalene, ethyl octanoate, diethyl sebacate, octyl octanoate, heptylbenzene, menthyl isovalerate, cyclohexyl hexanoate, or mixtures of these solvents.

[0166] Therefore, the present invention also provides a formulation or composition comprising at least one compound of the present invention and at least one other compound. The other compound may be, for example, a solvent, particularly one of the solvents described above or a mixture of these solvents. If the other compound contains a solvent, the mixture is referred to herein as a formulation. Alternatively, the other compound may be at least one other organic or inorganic compound also used in electronic devices, such as a luminescent compound and / or other matrix material. Preferably, the at least one other compound is selected from phosphors, phosphorescent materials, luminescent materials exhibiting TADF, host materials, electron transport materials, electron injection materials, hole conduction materials, hole injection materials, electron blocking materials, and hole blocking materials, preferably a host material.

[0167] This invention also provides the use of the compounds of this invention in electronic devices, particularly organic electroluminescent devices. Preferably, the compounds of this invention are used in electronic devices as host materials, electron transport materials, electron injection materials, or hole blocking materials.

[0168] The present invention also provides an electronic device comprising at least one compound of the present invention. In the context of the present invention, an electronic device is a device comprising at least one layer and said layer comprising at least one organic compound. The component may also comprise a layer of inorganic material or a layer formed entirely of inorganic material.

[0169] The electronic device is more preferably selected from organic electroluminescent devices (OLED, sOLED, PLED, LEC, etc.), and more preferably organic light-emitting diodes (OLED), small molecule-based organic light-emitting diodes (sOLED), polymer-based organic light-emitting diodes (PLED), light-emitting electrochemical cells (LEC), organic laser diodes (O-lasers), and organic plasma light-emitting devices (DM Koller et al., Nature Photonics 2008, 1-4), organic integrated circuits (O-IC), organic field-effect transistors (O-FET), organic thin-film transistors (O-TFT), organic light-emitting transistors (O-LET), organic solar cells (O-SC), organic optical detectors, organic photosensors, organic field quenching devices (O-FQD), and organic electrical sensors, preferably organic electroluminescent devices (OLED, sOLED, PLED, LEC, etc.), more preferably organic light-emitting diodes (OLED), small molecule-based organic light-emitting diodes (sOLED), polymer-based organic light-emitting diodes (PLED), especially phosphorescent OLEDs.

[0170] The organic electroluminescent device comprises a cathode, an anode, and at least one emitting layer. In addition to these layers, it may also comprise other layers, such as one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, and / or charge generation layers in each case. Similarly, an intermediate layer, for example, with exciton blocking functionality, may be introduced between two emitting layers. However, it should be noted that not every single one of these layers is necessary. In this case, the organic electroluminescent device may contain one emitting layer, or it may contain multiple emitting layers. If multiple emitting layers are present, these emitting layers preferably have multiple luminescence maximum values ​​between 380 nm and 750 nm, resulting in overall white emission; in other words, a variety of fluorescent or phosphorescent luminescent compounds are used in the emitting layers. A system with three emitting layers is particularly preferred, wherein the three layers exhibit blue, green, and orange or red emission. The organic electroluminescent device of the present invention can also be a tandem electroluminescent device, especially a white emitting OLED.

[0171] Depending on the exact structure, the compounds of the present invention can be used in different layers. Preferably, the compounds of the present invention are used as host materials, electron transport materials, electron injection materials, or hole blocking materials in organic light-emitting devices. Preferably, the organic light-emitting device contains the compound of formula (I) or the preferred embodiments described above as a matrix material for phosphorescent emitters or emitters exhibiting TADF (thermally activated delayed fluorescence), especially a matrix material for phosphorescent emitters, in the emitting layer. It is also preferred to have an organic light-emitting device in which the compounds of the present invention are present in the electron injection layer, electron transport layer, and / or hole blocking layer. More preferably, the compounds of the present invention are used as a matrix material for phosphorescent emitters in the emitting layer, especially for red, orange, blue, green, or yellow phosphorescent emitters, preferably for blue or green phosphorescent emitters.

[0172] Preferably, the organic electroluminescent device comprises at least one light-emitting layer and at least one electron transport layer, wherein the electron transport layer contains a compound according to the invention.

[0173] When the compounds of the present invention are used as matrix materials for phosphorescent compounds in the luminescent layer, they are preferably used in combination with one or more phosphorescent materials (triple emitters). In the context of this invention, phosphorescence should be understood as emission from an excited state having a high spin multiplicity, i.e., spin state > 1, particularly emission from an excited triplet state. In the context of this application, all luminescent complexes containing transition metals or lanthanides, particularly all iridium, platinum, and copper complexes, should be considered phosphorescent compounds.

[0174] Based on the total mixture of the luminescent material and the matrix material, the mixture of the compound of the present invention and the luminescent compound contains 99 vol% to 1 vol%, preferably 98 vol% to 10 vol%, more preferably 97 vol% to 60 vol%, and especially 95 vol% to 80 vol% of the compound of the present invention. Accordingly, based on the total mixture of the luminescent material and the matrix material, the mixture contains 1 vol% to 99 vol%, preferably 2 vol% to 90 vol%, more preferably 3 vol% to 40 vol%, and especially 5 vol% to 20 vol% of the luminescent material.

[0175] In one embodiment of the invention, the compound of the invention is used herein as the sole matrix material (“monobody”) of the luminescent body, preferably a phosphorescent luminescent body.

[0176] Another embodiment of the present invention is that the compound of the present invention is used as a matrix material for a phosphorescent luminescent material in combination with other matrix materials. Suitable matrix materials that can be used in combination with the compounds of the present invention are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or aromatic sulfones (e.g., according to WO 2004 / 013080, WO 2004 / 093207, WO 2006 / 005627 or WO2010 / 006680), triarylamines, carbazole derivatives (e.g., CBP (N,N-dicarbazolylbiphenyl) or carbazole derivatives disclosed in WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 288381, EP 1205527, WO 2008 / 086851 or WO 2013 / 041176), indole-carbazole derivatives (e.g., according to WO 2007 / 063754 or WO 2008 / 056746), indo-carbazole derivatives (e.g., according to WO 2007 / 063754 or WO 2008 / 056746), and indo-carbazole derivatives (e.g., according to WO 2004 / 013080, US 2004 / 093207, WO 2006 / 005627 or WO 2010 / 006680). 2010 / 136109, WO 2011 / 000455, WO 2013 / 041176 or WO 2013 / 056776), azacarbazole derivatives (e.g. according to EP 1617710, EP 1617711, EP 1731584, JP2005 / 347160), bipolar matrix materials (e.g. according to WO 2007 / 137725), silanes (e.g. according to WO 2005 / 111172), borazine or borate esters (e.g. according to WO 2006 / 117052), triazine derivatives (e.g. according to WO2007 / 063754, WO 2008 / 056746, WO 2010 / 015306, WO 2011 / 057706, WO 2011 / 060859 or WO2011 / 060877), zinc complexes (e.g., according to EP 652273 or WO 2009 / 062578), silylated diazacyclopentane or silylated tetrazacyclopentane derivatives (e.g., according to WO 2010 / 054729), phosphorus diazacyclopentane derivatives (e.g., according to WO2010 / 054730), bridged carbazole derivatives (e.g., according to WO 2011 / 042107, WO 2011 / 060867, WO 2011 / 088877 and WO 2012 / 143080), triphenylide derivatives (e.g., according to WO 2012 / 048781), dibenzofuran derivatives (e.g., according to WO 2015 / 169412, WO 2016 / 015810, WO 2016 / 023608, WO 2017 / 148564 or WO2017 / 148565) or bicarbazole (e.g., according to JP 3139321 B2).

[0177] Similarly, other phosphorescent emitters that emit light at wavelengths shorter than the actual emitter can exist as co-substrate in the mixture. Particularly good results can be achieved when the emitter used is a red phosphorescent emitter, and the co-substrate used in combination with the compound of the present invention is a yellow phosphorescent emitter.

[0178] Furthermore, the co-matrix used can be a compound, as described in, for example, WO 2010 / 108579, that does not participate in charge transport to a significant extent. Compounds with large band gaps and which themselves do not participate in charge transport in the luminescent layer to a significant extent are particularly suitable as co-matrix materials in combination with the compounds of the present invention. Such materials are preferably pure hydrocarbons. Examples of such materials can be found, for example, in WO 2009 / 124627 or WO 2010 / 006680. In this case, it should be emphasized that the compounds of the present invention have advantageous properties in the absence of specific functional groups, such as hole transport groups and / or electron transport groups.

[0179] Suitable phosphorescent compounds (= triplet emitters) are particularly those that emit light when properly excited, preferably in the visible region, and further contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, more preferably greater than 56 and less than 80, especially a metal having that atomic number. Preferred phosphorescent emitters used are compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium, especially compounds containing iridium or platinum.

[0180] Examples of the aforementioned luminescent materials can be found in the following applications: WO 00 / 70655, WO 2001 / 41512, WO 2002 / 02714, WO 2002 / 15645, EP 1191613, EP 1191612, EP 1191614, WO 05 / 033244, WO 05 / 019373, US 2005 / 0258742, WO 2009 / 146770, WO 2010 / 015307, WO 2010 / 031485, WO 2010 / 054731, WO 2010 / 054728, WO 2010 / 086089, WO 2010 / 099852, WO 2010 / 102709, WO 2011 / 032626、WO 2011 / 066898、WO 2011 / 157339、WO 2012 / 007086、WO 2014 / 008982、WO 2014 / 023377、WO 2014 / 094961、WO 2014 / 094960、WO 2015 / 036074, WO 2015 / 104045, WO 2015 / 117718, WO 2016 / 015815, WO 2016 / 124304, WO 2017 / 032439 and WO 2018 / 011186. Generally, all phosphorescent complexes known to those skilled in the art for use in phosphorescent electroluminescent devices are suitable, and those skilled in the art will be able to use other phosphorescent complexes without inventive effort.

[0181] The following table lists examples of phosphorescent dopants:

[0182] The compounds of this invention are also particularly suitable as matrix materials for phosphorescent emitters in organic electroluminescent devices, as described in, for example, WO 98 / 24271, US 2011 / 0248247, and US2012 / 0223633. In these multicolor display components, an additional blue emitting layer is applied across all pixels, including pixels having colors other than blue, by vapor deposition.

[0183] In another embodiment of the invention, the organic electroluminescent device of the present invention does not contain any separate hole injection layer and / or hole transport layer and / or hole blocking layer and / or electron transport layer, meaning that the light-emitting layer is directly adjacent to the hole injection layer or anode, and / or the light-emitting layer is directly adjacent to the electron transport layer or electron injection layer or cathode, as described, for example, in WO 2005 / 053051. Furthermore, metal complexes identical or similar to those in the light-emitting layer can be used as hole transport or hole injection materials directly adjacent to the light-emitting layer, as described, for example, in WO 2009 / 030981.

[0184] In the other layers of the organic electroluminescent device of the present invention, any material commonly used in the prior art can be used. Therefore, those skilled in the art will be able to combine any material known for use in organic electroluminescent devices with the compound of formula (I) of the present invention or the preferred embodiments described above without any inventive effort.

[0185] Furthermore, an organic electroluminescent device is preferred, characterized by coating one or more layers via a sublimation method. In this case, the material is sublimated in a vacuum sublimation system at a temperature of less than 10... -5 millibars, preferably less than 10 -6 Vapor deposition is applied at an initial pressure of millibars. However, the initial pressure can be even lower, for example, below 10. -7 millibar.

[0186] Also preferred is an organic electroluminescent device, characterized by coating one or more layers by an OVPD (organic vapor deposition) method or by means of carrier gas sublimation. In this case, the material is in 10 -5 The material is applied at a pressure of millibar to 1 bar. A special case of this method is the OVJP (Organic Vapor Jet Printing) method, in which the material is applied directly through a nozzle and thereby structured.

[0187] Furthermore, an organic electroluminescent device is preferred, characterized by the formation of one or more layers from a solution, for example, by spin coating, or by any printing method such as screen printing, flexographic printing, offset printing, LITI (photoinduced thermal imaging), thermal transfer, inkjet printing, or nozzle printing. For this purpose, a soluble compound is required, for example, through suitable substitution.

[0188] The formulation for applying the compound of formula (I) or the preferred embodiment thereof described above is novel. Therefore, the present invention also provides a formulation comprising at least one solvent and the compound of formula (I) or the preferred embodiment thereof described above.

[0189] Furthermore, a mixing method is feasible, in which, for example, one or more layers are applied from a solution and one or more other layers are applied by vapor deposition.

[0190] These methods are generally known to those skilled in the art and can be applied to organic electroluminescent devices containing the compounds of the present invention without any inventive effort.

[0191] Compared to the prior art, the compounds of the present invention and the organic electroluminescent devices of the present invention are particularly noteworthy due to their low refractive index (RI). Furthermore, these compounds and the organic electroluminescent devices derived therefrom exhibit improved lifetimes. Meanwhile, other electronic properties of the electroluminescent devices, such as efficiency or operating voltage, remain at least as good. In another variant, the compounds of the present invention and the organic electroluminescent devices of the present invention particularly exhibit improved efficiency and / or operating voltage, as well as a longer lifetime, compared to the prior art.

[0192] Compared with the prior art, the electronic device of the present invention, especially the organic electroluminescent device, is noteworthy for one or more of the following surprising advantages: 1. The preferred embodiments of the present invention, comprising the compound of formula (I) or as described in the context, particularly in electronic devices, especially organic electroluminescent devices, exhibit excellent efficiency as a matrix material or as an electronically conductive material. In this case, the preferred embodiments of the present invention, comprising the compound of formula (I) or as described in the context, achieve low operating voltage when used in electronic devices.

[0193] 2. Compounds comprising formula (I) or preferred embodiments described in the context, particularly electronic devices as matrix materials or electronically conductive materials, especially organic electroluminescent devices, exhibit excellent lifetime. In this case, these compounds particularly achieve low roll-off, i.e., the power efficiency of the device decreases only slightly at high brightness.

[0194] 3. The preferred embodiments of the present invention, in the form of formula (I) or in the context thereof, exhibit extremely high stability and lifespan.

[0195] 4. The preferred embodiments comprising the compound of formula (I) or described in the context, particularly electronic devices, especially organic electroluminescent devices, having extremely low refractive indices, are particularly useful as a matrix material or as an electronically conductive material.

[0196] 5. The preferred embodiments described in the context of formula (I) avoid the formation of light loss channels in electronic devices, especially organic electroluminescent devices. Therefore, these devices are characterized by high PL efficiency of the light emitter and the resulting high EL efficiency, as well as excellent energy transfer from the matrix to the dopant.

[0197] 6. The preferred embodiments described in the context of the compound of formula (I) have excellent glass film formation.

[0198] 7. The preferred embodiments of the compound of formula (I) or the context described herein form excellent films from solution.

[0199] These advantages are not accompanied by excessive degradation of other electronic properties.

[0200] It should be noted that the scope of this invention covers variations of the embodiments described herein. Unless expressly excluded, any feature disclosed in this invention may be interchanged with alternative features serving the same or equivalent or similar purpose. Therefore, unless otherwise stated, any feature disclosed in this invention should be considered as an example of a general series or an equivalent or similar feature.

[0201] Unless specific features and / or steps are mutually exclusive, all features of the invention can be combined with each other in any way. This is especially true of preferred features of the invention. Similarly, features that are not necessarily combined can be used alone (rather than in combination).

[0202] It should also be noted that many features, especially those of the preferred embodiments of the invention, should be considered inventive in themselves, rather than merely as some embodiments of the invention. These features may be sought independently as additions or alternatives to any currently claimed invention.

[0203] The technical teachings disclosed in this invention can be refined and combined with other embodiments.

[0204] The invention is illustrated in more detail by way of the following examples, but is not intended to limit the invention thereto. Those skilled in the art will be able to practice the invention, prepare other compounds of the invention and use them in electronic devices, or employ the methods of the invention throughout the scope of the disclosure, without inventive effort, using the information given.

[0205] Example: Unless otherwise specified, the following synthesis shall be carried out in a dry solvent under a protective atmosphere. Solvents and reagents are available from, for example, Sigma-Aldrich or ABCR. The corresponding numbers in square brackets or the numbers cited for individual compounds relate to the CAS numbers of the compounds known from the literature. In the case of compounds that may have multiple isomers, enantiomers, diastereomers, or tautomers, one form is shown in a representative manner.

[0206] A: Based on the known synthon S from the literature:

[0207] B: Preparation of synthon S: Example S1: 1) S1a:

[0208] The procedure was similar to that of M. Tashiro et al., J. Org. Chem., 1982, 47 (23), 4426, compound 28. Starting materials: 36.7 g (100 mmol) of LS1, 19.0 ml (200 mmol) of BBr3. Yield: 26.2 g (75 mmol), 75%; Purity: 97%, according to... 1 H NMR.

[0209] 2) S1:

[0210] The procedure was similar to that of S. Hu et al., J. Mol. Struct., 2023, 1286, 135565, compound 1o. Starting material: 35.3 g (100 mmol) of S1a. The crude product was recrystallized from acetonitrile. Yield: 37.3 g (77 mmol), 77%; Purity: 98%, according to 1 H NMR.

[0211] The following compounds can be prepared similarly:

[0212] Tf: Trifluoromethanesulfonyl group

[0213] Example S100:

[0214] A well-stirred mixture of 48.5 g (100 mmol) of S1, 50.8 g (200 mmol) of bis(pinacol)diborane [73183-34-3], 29.5 g (300 mmol) of anhydrous potassium acetate [127-08-2], 200 g of glass beads (3 mm in diameter), 3.7 g (5 mmol) of bis(tricyclohexylphosphino)palladium(II) chloride [29934-17-6], and 1500 ml of disulfane was stirred at 100 °C for 18 hours. The mixture was filtered, and simultaneously passed through a diatomaceous earth bed while hot as a disulfane slurry. The filtrate was concentrated under reduced pressure, and the residue was dissolved in 500 ml of dichloromethane (DCM). The organic phase was washed twice with 300 ml of water and once with 200 ml of saturated sodium chloride solution, and dried over magnesium sulfate. The DCM slurry mixture was obtained by vacuum filtration through a silica gel bed. The filtrate was concentrated to dryness, and the oily substance was crystallized by adding 50 ml of acetonitrile and 100 ml of ethanol. The solid was obtained by vacuum filtration, dried, and separated chromatographically (using a Torrent automated column system from Semrau). Yield: 37.3 g (80 mmol), 80%; Purity: approximately 97%, based on... 1 H NMR.

[0215] The following compounds can be prepared similarly:

[0216] C: Preparation of compound B of the present invention: Example B1

[0217] A well-stirred mixture of 48.5 g (100 mmol) of S1, 47.9 g (110 mmol) of 4,6-diphenyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl]-1,3,5-triazine [1313018-07-3], 46.1 g (200 mmol) of tripotassium phosphate monohydrate, 1.16 g (1 mmol) of tetra(triphenylphosphine)palladium(O), 500 ml of dimethyl sulfoxide (DMSO), and 100 g of glass beads (3 mm in diameter) was stirred at 80 °C for 16 hours. After conversion, the mixture was cooled, glass beads were removed by decanting, and most of the DMSO was removed under reduced pressure. 300 ml of methanol and 300 ml of water were added to the residue, and the crude product was filtered off. The residue was washed twice with water (200 ml each time) and twice with methanol (200 ml each time), and dried under reduced pressure. The crude product was dissolved in 500 ml of DCM and filtered through a diatomaceous earth bed as a DCM slurry. The filtrate was concentrated to dryness, and the residue was extracted by stirring with 200 ml of hot methanol. The crude product was filtered off, washed twice with methanol (50 ml each time), and dried under reduced pressure. Further purification was achieved by repeated hot extraction crystallization (using organic solvents or combinations thereof, preferably acetonitrile-DCM, 1:3 to 3:1 vv) or by chromatography and fractional sublimation or heat treatment under high vacuum. Yield: 44.4 g (69 mmol), 69%; Purity: approximately 99.9%, according to HPLC. As an alternative, or in the case of using chloride, Suzuki coupling can be performed in a toluene / dimethylamine / water system (4:1:5 vvv) containing 1 mmol of palladium(II) acetate and 2 mmol of S-Phos or X-Phos.

[0218] The following compounds can be prepared similarly:

[0219] Example B450:

[0220] A mixture of 46.3 g (100 mmol) of S100, 26.8 g (100 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine [3842-55-5], 42.5 g (200 mmol) of tripotassium phosphate, 860 mg (2 mmol) of S-Phos, 225 mg (1 mmol) of palladium(II) acetate, 400 ml of toluene, 100 ml of disulfide, and 300 ml of water was heated under reflux for 16 hours. After cooling, the organic phase was removed, washed twice with water (200 ml each time) and once with 200 ml of saturated sodium chloride solution, and dried over magnesium sulfate. The drying agent was filtered through a diatomaceous earth bed as a toluene slurry. The filtrate was concentrated to dryness, and the residue was extracted with 200 ml of hot methanol under stirring, filtered, and dried under reduced pressure.

[0221] Further purification was achieved in each case by repeated hot extraction crystallization (usually using organic solvents or combinations thereof, preferably acetonitrile-DCM, 1:3 to 3:1 vv) or by chromatography and fractional sublimation or heat treatment under high vacuum. Yield: 41.6 g (73 mmol), 73%. Purity: 99.9%, according to HPLC.

[0222] The following compounds can be prepared similarly:

[0223] Example: OLED Manufacturing

[0224] The OLEDs of the present invention and the OLEDs according to the prior art are manufactured by the general method according to WO 2004 / 058911, with the method adapted to suit the conditions described herein (variations in layer thickness, materials used).

[0225] In the following examples, results for various OLEDs are presented. Clean glass plates coated with a 50 nm thick layer of structured ITO (indium tin oxide) (cleaned in a Miele laboratory glass washer, Merck Extran detergent) were pretreated with UV ozone for 25 minutes (UVP PR-100 UV ozone generator). These coated glass plates form the substrate for applying the OLED.

[0226] a) Blue fluorescent OLED module – BF: Compound B of this invention can be used in hole blocking layers (HBLs) and electron transport layers (ETLs). All materials are applied in a vacuum chamber via thermal vapor deposition. The emissive layer (EML) is always composed of at least one matrix material (host material) SMB (see Table 1) and a light-emitting dopant (dopant, emitting element) D added to one or more matrix materials by co-evaporation in a specific volume ratio. Details given in the form of SMB:D (97%:3%) refer to the presence of material SMB at a volume ratio of 97% and dopant D at a ratio of 3%. Similarly, the electron transport layer may also consist of a mixture of the two materials; see Table 1. Materials used to manufacture OLEDs are shown in Table 5, or related to the synthesis examples detailed above.

[0227] OLEDs were characterized using standard methods. For this purpose, the electroluminescence spectrum was determined, and current efficiency (measured in cd / A), power efficiency (measured in lm / W), and external quantum efficiency (EQE, measured as a percentage) were determined as functions of luminance, calculated using the current-voltage-luminance characteristics (IUL characteristics) exhibiting Lambertian emission properties. The report is based on 1000 cd / m². 2 EQE (%) and voltage (V) at brightness.

[0228] The OLED has the following layer structure: base The hole injection layer (HIL) consists of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm in diameter. Hole transport layer (HTL), composed of HTM1, 180 nm Electron blocking layer (EBL), see Table 1 Emissive layer (EML), see Table 1 Hole blocking layer (HBL), see Table 1 Electron transport layer (ETL), see Table 1 Electron injection layer (EIL), composed of ETM2, 1 nm The cathode, made of aluminum, is 100 nm in diameter.

[0229] Table 1: Structure of Blue Fluorescent OLED Module

[0230] Table 2: Results of Blue Fluorescent OLED Module

[0231] b) Phosphorescent OLED modules: Compound B of this invention can be used as an electron conduction matrix material (host material) (eTMM) in hole blocking layer (HBL), electron transport layer (ETL), and light-emitting layer (EML). For this purpose, all materials are applied in a vacuum chamber by thermal vapor deposition. The light-emitting layer is always composed of at least one or more matrix materials M and phosphorescent dopant Ir added to one or more matrix materials in a specific volume ratio by co-evaporation. Details given in the form of M1:M2:Ir (55%:35%:10%) refer to materials M1 being present in the layer at a volume ratio of 55%, M2 at a volume ratio of 35%, and Ir at a volume ratio of 10%. Similarly, the electron transport layer may also be composed of a mixture of the two materials. The exact structure of the OLED can be seen in Table 3. The materials used to manufacture the OLED are shown in Table 5, or related to the synthesis examples detailed above.

[0232] OLEDs were characterized using standard methods. For this purpose, the electroluminescence spectrum was determined, and current efficiency (measured in cd / A), power efficiency (measured in lm / W), and external quantum efficiency (EQE, measured as a percentage) were determined as functions of luminance, calculated using the current-voltage-luminance characteristics (IUL characteristics) exhibiting Lambertian emission properties. The report is based on 1000 cd / m². 2 EQE (%) and voltage (V) at brightness.

[0233] The OLED has the following layer structure: base The hole injection layer (HIL) consists of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm in diameter. The hole transport layer (HTL), composed of HTM1, is 180 nm for blue and 50 nm for green, yellow, and red. Electron blocking layer (EBL), see Table 3 Emissive Layer (EML), see Table 3 Hole blocking layer (HBL), see Table 3 Electron transport layer (ETL), see Table 3 Electron injection layer (EIL), composed of ETM2, 1 nm The cathode, made of aluminum, is 100 nm in diameter.

[0234] Table 3: Structure of Phosphorescent OLED Modules

[0235] Table 4: Results of phosphorescent OLED modules:

[0236] Table 5: Structural Formulas of Materials Used

Claims

1. A compound of formula (I), Formula (I) The Q group is selected from the structure of formula (Q-1). Equation (Q-1) The dashed bond represents a bond bonded to the L group, or, in the case of q=0, a bond bonded to the dibenzofuran basic skeleton of formula (I); s is 1, 2, or 3, where s is marked as 1 in the case of q=0; and other symbols are as follows: X is the same or different in each case and is N or CR. c In which at least one X group is N; X a The same or different in each case and for N, CR a Or when this group combines with another group at this position, X a Let C be a ring containing no more than two X's. a The group is N; X b The same or different in each case and for N, CR b Or when this group combines with another group at this position, X b Let C be a ring containing no more than two X's. b The group is N; L may be the same or different in each case and is a combination of 6 to 40 aromatic ring atoms and in each case can be one or more non-H R atoms. d Divalent, trivalent, or tetravalent aromatic or heteroaromatic ring systems with substituted groups; q is 0 or 1, where q=0 means that the L group is absent and the Q group is directly bonded to the relevant atom of the dibenzofuran basic skeleton of formula (I), such as a carbon atom; R may be the same or different in each case and is a straight-chain alkyl, alkoxy, or thioalkoxy group having 1 to 10 carbon atoms or a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 10 carbon atoms, each of which may be one or more non-H R groups. 2 Group substitution, each of which can be replaced by one or more non-H R groups. 2 Group substitution, wherein two or more substituents R together can form a ring; R a R b The same or different in each case and are H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar)2, N(R) c )2, C(=O)N(Ar)2, C(=O)N(R) c )2, C(Ar)3, C(R) c )3, Si(Ar)3, Si(R) c )3, Ge(Ar)3, Ge(R) c )3, B(Ar)2, B(R) c )2, C(=O)Ar, C(=O)R c , P(=O)(Ar)2, P(=O)(R c )2, P(Ar)2, P(R) c )2, S(=O)Ar, S(=O)R c S(=O)2Ar, S(=O)2R c OSO2Ar, OSO2R c A straight-chain alkyl, alkoxy, or thioalkoxy group having 1 to 40 carbon atoms, or an alkenyl or alkynyl group having 2 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 20 carbon atoms, wherein each of the alkyl, alkoxy, thioalkoxy, alkenyl, or alkynyl groups may be derived from one or more non-H R groups. c Group substitution, wherein one or more non-adjacent CH2 groups can be replaced by R c C=CR c C≡C, Si(R) c 2. C=O, C=S, C=Se, C=NR c -C(=O)O-, -C(=O)NR c -、NR c P(=O)(R) c (), -O-, -S-, SO or SO2, or have 5 to 60 aromatic ring atoms and in each case can be replaced by one or more non-H R c Aromatic or heteroaromatic ring systems with substituted groups, or having 5 to 60 aromatic ring atoms and being substituted by one or more R groups. c The aryloxy or heteroaryloxy group substituted by the radical; simultaneously, two R groups... a R b Groups together or one R a R b Group and another group, especially R c Groups can also form rings; Ar may be the same or different in each case and is an R with 5 to 40 aromatic ring atoms and can be separated by one or more non-H atoms. c Aromatic or heteroaromatic ring systems with substituted groups, wherein if X is CR c Then the Ar group can react with the R group of the X group. c The groups together form a ring; R c R d The same or different in each case and are H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar')2, N(R) 1 )2,C(=O)N(Ar')2,C(=O)N(R 1 )2, C(Ar')3, C(R) 1 )3, Si(Ar')3, Si(R) 1 )3, Ge(Ar')3, Ge(R) 1 )3, B(Ar')2, B(R) 1 )2,C(=O)Ar',C(=O)R 1 ,P(=O)(Ar')2,P(=O)(R 1 )2, P(Ar')2, P(R) 1 )2,S(=O)Ar',S(=O)R 1 S(=O)2Ar', S(=O)2R 1 OSO2Ar', OSO2R 1 The alkyl, alkoxy, or thioalkoxy group having 1 to 40 carbon atoms, or an alkenyl or alkynyl group having 2 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 20 carbon atoms, wherein the alkyl, alkoxy, thioalkoxy, alkenyl, or alkynyl group in each case may be one or more non-H R 1 Group substitution, wherein one or more non-adjacent CH2 groups can be replaced by R 1 C=CR 1 C≡C, Si(R) 1 2. C=O, C=S, C=Se, C=NR 1 -C(=O)O-, -C(=O)NR 1 -、NR 1 P(=O)(R) 1 (), -O-, -S-, SO or SO2, or have 5 to 60 aromatic ring atoms and in each case can be replaced by one or more non-H R 1 Aromatic or heteroaromatic ring systems with substituted groups, or having 5 to 60 aromatic ring atoms and being substituted by one or more non-H R groups. 1 A group-substituted aryloxy or heteroaryloxy group; simultaneously, selected from R c R d Two groups together, or R c or R d Group and another group, especially R a or R b Groups can also form rings; Ar' is the same or different in each case and is a group of 5 to 60 aromatic ring atoms that can be separated by one or more non-H R atoms. 1 Aromatic or heteroaromatic ring systems with substituted groups; wherein... Two Ar' groups bonded to the same carbon, silicon, nitrogen, phosphorus, or boron atom can also bond via a single bond or a bond selected from B(R) 1 ), C(R 1 )2、Si(R 1 2. C=O, C=NR 1 C=C(R) 1 )2、O、S、S=O、SO2、N(R 1 ), P(R 1 ) and P(=O)R 1 The bridges connect the bases of the bridges to each other; R 1 The same or different in each case and are H, D, F, Cl, Br, I, CN, NO2, N(Ar'')2, N(R) 2 )2,C(=O)Ar'',C(=O)R 2 ,P(=O)(Ar'')2,P(Ar'')2,B(Ar'')2,B(R 2 )2, C(Ar'')3, C(R) 2 )3, Si(Ar'')3, Si(R 2 )3, Ge(Ar'')3, Ge(R 2 3, a straight-chain alkyl, alkoxy, or thioalkoxy group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 40 carbon atoms, or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted with one or more non-H R 2 Group substitution, wherein one or more non-adjacent CH2 groups can be replaced by -R 2 C=CR 2 -、-C≡C-、Si(R 2 2. C=O, C=S, C=Se, C=NR 2 -C(=O)O-, -C(=O)NR 2 -、NR 2 P(=O)(R) 2 The atom is replaced by -O-, -S-, SO or SO2 and one or more of the hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or it has 5 to 60 aromatic ring atoms and in each case may be replaced by one or more R 2 Aromatic or heteroaromatic ring systems with substituted groups, or having 5 to 60 aromatic ring atoms and being substituted by one or more R groups. 2 A group-substituted aryloxy or heteroaryloxy group, or a group having 5 to 60 aromatic ring atoms and being substituted by one or more non-H R groups. 2 Group-substituted aralkyl or heteroaralkyl groups, or combinations thereof; simultaneously, two or more R groups 1 The groups together can form a ring, in which one or more R groups can form a ring. 1 The group can form a ring with another part of the compound; Ar'' is the same or different in each case and has 5 to 30 aromatic ring atoms and can be denoted by one or more R''. 2 Aromatic or heteroaromatic ring systems with substituted groups; wherein two Ar" groups bonded to the same carbon, silicon, nitrogen, phosphorus, or boron atom can also be bonded by a single bond or selected from B(R) 2 ), C(R 2 )2、Si(R 2 2. C=O, C=NR 2 C=C(R) 2 )2、O、S、S=O、SO2、N(R 2 ), P(R 2 ) and P(=O)R 2 The bridges connect the bases of the bridges to each other; R 2 In each case, the same or different aliphatic hydrocarbon groups selected from H, D, F, CN, having 1 to 20 carbon atoms, or aromatic or heteroaromatic ring systems having 5 to 30 aromatic ring atoms in which one or more hydrogen atoms can be replaced by D, F, Cl, Br, I, or CN, and said aromatic or heteroaromatic ring systems can be replaced by one or more alkyl groups each having 1 to 4 carbon atoms; simultaneously, two or more substituents R 2 Together they can form a ring.

2. The compound according to claim 1, characterized in that... The compound conforms to formula (IIa), (IIb), (IIc), or (IId). Equation (IIa) Equation (IIb) Equation (IIc) Equation (IId) The symbols R, Q, L, q, s, R a R b and R c It has the definition given in claim 1, where j is 2 or 3, i is 1 or 2, k is 0 or 1, wherein the sum of the two j is 5, the sum of the two i is 3, and the sum of j and k is 3.

3. The compound according to claim 1 or 2, characterized in that... Formula-(L) q -(Q) s The Q group is selected from structures of formulas (Q-2) to (Q-16). Equation (Q-2) Equation (Q-3) Equation (Q-4) Equation (Q-5) Equation (Q-6) Equation (Q-7) Equation (Q-8) Equation (Q-9) Equation (Q-10) Equation (Q-11) Equation (Q-12) Equation (Q-13) Equation (Q-14) Equation (Q-15) Equation (Q-16) The dashed bond represents a bond bonded to the L group, or, in the case of q=0, a bond bonded to the dibenzofuran-based skeleton of formula (I), denoted by R. c Ar has the definition given in claim 1, and the other symbols are as follows: X c The same or different in each case and is N or CR c Each ring contains no more than two X's. c The group is N; Y c Selected from C(R) c )2、Si(R c )2、Ge(R c 2. NR c 、O or S.

4. The compound according to one or more of claims 1 to 3, characterized in that... At least one Ar group in formulas (Q-1) to (Q-16) is selected from phenyl, biphenyl, terphenyl, tetraphenyl, fluorene, spirodifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, benzimidazole-benzimidazole, dibenzofuran, dibenzothiophene, indole-carbazole, indolo-carbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, or biphenylide, each of which may be substituted with one or more non-H R groups. c Group substitution.

5. The compound according to one or more of claims 1 to 4, characterized in that... The compound conforms to at least one of the following formulas (III-1) to (III-27): Equation (III-1) Equation (III-2) Equation (III-3) Equation (III-4) Equation (III-5) Equation (III-6) Equation (III-7) Equation (III-8) Equation (III-9) Equation (III-10) Equation (III-11) Equation (III-12) Equation (III-13) Equation (III-14) Equation (III-15) Equation (III-16) Equation (III-17) Equation (III-18) Equation (III-19) Equation (III-20) Equation (III-21) Equation (III-22) Equation (III-23) Equation (III-24) Equation (III-25) Equation (III-26) Equation (III-27) The symbols R, Q, L, q, s, R a R b and R c It has the definition given in claim 1, and j is 2 or 3.

6. The compound according to one or more of claims 1 to 5, characterized in that... The L group may be the same or different in each case and is selected from divalent, trivalent, or tetravalent phenyl, biphenyl, terphenyl, tetraphenyl, fluorene, spirodifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, benzimidazole-benzimidazole, dibenzofuran, dibenzothiophene, indole-carbazole, indolo-carbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, or biphenylidene, each of which may be substituted with one or more non-H R groups. d Group substitution.

7. The compound according to one or more of claims 1 to 6, characterized in that, In formulas (I), (IIa), (IIb), (IIc), (IId), or (III-1) to (III-27), the Q group conforms to formula (Q-2), s is labeled 1 and q is labeled 0, wherein at least one Ar group in the formula is selected from phenyl, biphenyl, and dibenzofuran, and each of the groups can be converted by one or more non-H R groups. c Group substitution; or In formulas (I), (IIa), (IIb), (IIc), (IId), or (III-1) to (III-27), the Q group conforms to formula (Q-3), (Q-11), (Q-12), or (Q-13), denoted by s as 1, and denoted by q as 0, wherein at least one Ar group in the formula is selected from phenyl, biphenyl, or dibenzofuran, and each of the groups can be converted by one or more non-H R groups. c Group substitution; or In formulas (I), (IIa), (IIb), (IIc), (IId), or (III-1) to (III-27), the Q group conforms to formula (Q-7), (Q-14), (Q-15), or (Q-16), denoted by s as 1, and denoted by q as 0, wherein at least one Ar group in the formula is selected from phenyl, biphenyl, or dibenzofuran, and each of the groups can be converted by one or more non-H R groups. c Group substitution.

8. The compound according to one or more of claims 1 to 6, characterized in that, In formulas (I), (IIa), (IIb), (IIc), (IId), or (III-1) to (III-27), the Q group conforms to formula (Q-2), s is labeled 1, and q is labeled 1, wherein the L group is selected from divalent phenyl, biphenyl, dibenzofuran, and carbazole, and each of the groups can be substituted by one or more non-H R groups. d Group substitution, wherein at least one Ar group in the formula is selected from phenyl, biphenyl, dibenzofuran, and each of the groups can be substituted with one or more non-H R groups. c Group substitution; or In formulas (I), (IIa), (IIb), (IIc), (IId), or (III-1) to (III-27), the Q group conforms to formula (Q-3), (Q-11), (Q-12), or (Q-13), denoted as s and q, wherein the L group is selected from divalent phenyl, biphenyl, dibenzofuran, and carbazole, and each of the groups can be substituted by one or more non-H R groups. d Group substitution, wherein at least one Ar group in the formula is selected from phenyl, biphenyl, dibenzofuran, and each of the groups can be substituted with one or more non-H R groups. c Group substitution; or In formulas (I), (IIa), (IIb), (IIc), (IId), or (III-1) to (III-27), the Q group conforms to formula (Q-7), (Q-14), (Q-15), or (Q-16), denoted as s and q as 1, wherein the L group is selected from divalent phenyl, biphenyl, dibenzofuran, and carbazole, and each of the groups can be substituted by one or more non-H R groups. d Group substitution, wherein at least one Ar group in the formula is selected from phenyl, biphenyl, dibenzofuran, and each of the groups can be substituted with one or more non-H R groups. c Group substitution.

9. The compound according to one or more of claims 1 to 8, characterized in that... Formula-(L) q -(Q) s -(L) in q -Group representation-(L d ) o The structure of - is derived from the formula -(L). q -(Q) s The groups are selected from formula -(L d ) o -(Q) s The structure, where o is marked as 0, 1, 2, 3, 4 or 5, where o=0 means L d The group is absent and the Q group is directly bonded to the relevant atom of the dibenzofuran basic skeleton of formula (I), such as a carbon atom, and L d The group is selected from formula (L d -1) to formula (L) d The structure of -13): The dashed key indicates the connection point, and the other symbols are as follows: X d The same or different in each case and for N, CR d Or when this group combines with another group at this position, X d Let C be a ring containing no more than three X's. d The group is N, where R d It has the definition given in claim 1; Y d Selected from C(R) d 2. NR d , O or S; Wherein the formula -(L d ) o The structure of - is in the formula -(L) d ) o -(Q) s The label in the symbol is divalent when s=1, trivalent when s=2, and tetravalent when s=3.

10. The compound according to claim 9, characterized in that... L d The group is selected from formula (L d -14) to formula (L) d The structure of -33), The dashed key represents a connection site, symbol R. d With the definition given in claim 1, the symbol X d It has the definition given in claim 9, and the other symbols are as follows: i is 1 or 2; and j is 0, 1, or 2.

11. The compound according to one or more of claims 1 to 10, characterized in that... The compound conforms to one of the following formulas (IV-1) to (IV-4). Formula (IV-1) Formula (IV-2) Formula (IV-3) Formula (IV-4) The symbols R, X, X a X b Ar has the definition given in claim 1, and the symbol X d and Y d It has the definition given in claim 9.

12. The compound according to one or more of claims 1 to 11, characterized in that... The compound conforms to one of the following formulas (V-1) to (V-37). Equation (V-1) Equation (V-2) Equation (V-3) Equation (V-4) Equation (V-5) Equation (V-6) Equation (V-7) Equation (V-8) Equation (V-9) Equation (V-10) Equation (V-11) Equation (V-12) Equation (V-13) Equation (V-14) Equation (V-15) Equation (V-16) Equation (V-17) Equation (V-18) Equation (V-19) Equation (V-20) Equation (V-21) Equation (V-22) Equation (V-23) Equation (V-24) Equation (V-25) Equation (V-26) Equation (V-27) Equation (V-28) Equation (V-29) Equation (V-30) Equation (V-31) Equation (V-32) Equation (V-33) Equation (V-34) Equation (V-35) Equation (V-36) Equation (V-37) Among them, the symbols R and R a R b R c R d Ar has the definition given in claim 1, and the symbol Y d It has the definition given in claim 9, and the other symbols are defined as follows: n is 2 or 3.

13. The compound according to at least one of the preceding claims, characterized in that, The R group is methyl, ethyl, propyl, or three R groups bonded to the same carbon atom to form a bicycloalkyl or tricycloalkyl group having 9 or 10 carbon atoms, wherein these groups may be deuterated.

14. A formulation comprising at least one compound according to one or more of claims 1 to 13 and at least one other compound, wherein the other compound is preferably selected from one or more solvents.

15. A composition comprising at least one compound according to one or more of claims 1 to 13 and at least one other compound selected from fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF, host materials, electron transport materials, electron injection materials, hole conduction materials, hole injection materials, electron blocking materials, and hole blocking materials.

16. A method for preparing a compound according to one or more of claims 1 to 13, characterized in that... A dibenzofuran compound is synthesized and at least one nitrogen-containing heteroaromatic group is introduced, preferably through a nucleophilic aromatic substitution reaction or a coupling reaction.

17. Use of the compound or oligomer or polymer according to one or more of claims 1 to 13 in electronic devices, preferably as a host material, hole conducting material, hole injecting material or electron blocking material.

18. An electronic device comprising at least one compound according to one or more of claims 1 to 13.

19. The electronic device according to claim 18, wherein the electronic device is in the form of an organic electroluminescent device, characterized in that, The organic electroluminescent device comprises at least one light-emitting layer and at least one electron transport layer, wherein the electron transport layer contains a compound according to one or more of claims 1 to 13.

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