Electronic device

Abstract

The invention relates to an electronic device. Specifically, the present application relates to an electronic device comprising a compound having a specific formula in a layer between an anode and a light emitting layer, and further comprising a compound having a specific other formula in a layer between the light emitting layer and a cathode.

Description

[0001] This invention patent application is a divisional application of the invention patent application with international application number PCT / EP2020 / 072694, international application date of August 13, 2020, application number 202080056732.6 that entered the Chinese national phase, and invention title "Electronic Device". Technical Field

[0002] This application relates to electronic devices. Specifically, this application relates to an electronic device that includes a specific amine compound in a hole transport layer and a compound of a specific structural type in an electron transport layer. Background Technology

[0003] In the context of this application, "electronic device" should be understood to refer to so-called organic electronic devices that contain organic semiconductor materials as functional materials. More specifically, these should be understood to refer to OLEDs (Organic Light Emitting Devices). The term OLED should be understood to refer to an electronic device having one or more layers containing organic compounds and emitting light when a voltage is applied. The construction and general functional principles of OLEDs are known to those skilled in the art.

[0004] There has always been great interest in improving performance data in electronic devices, especially OLEDs.

[0005] A variety of materials are known for use as hole transport layers in electronic devices, most of which fall under the triarylamine class, such as N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (NPD) or tri-(4-carbazolyl-9-ylphenyl)amine (TCTA). Furthermore, spirodifluorenyl monoamines and fluorenyl monoamines have recently been identified as materials for hole transport layers.

[0006] The known electron transport compounds in electronic devices are also a variety of different compounds. In many cases, compounds with electron-deficient nitrogen-containing heteroaromatic six-membered rings, especially triazine derivatives, are used for this purpose. Summary of the Invention

[0007] In the context of this invention, it has been found that a combination of a specific spirodifluoreneamine or fluoreneamine in the hole transport layer with a specific electron-deficient nitrogen-containing six-membered heteroaromatic ring in the electron transport layer results in particularly good performance of electronic devices, especially long lifetime, high efficiency and low operating voltage.

[0008] Therefore, this application provides an electronic device comprising an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, characterized in that...

[0009] - There are one or more layers containing a compound of formula (H) between the anode and the light-emitting layer.

[0010]

[0011] Formula (H)

[0012] in:

[0013] Ar H1 In each case, they may be the same or different and are selected from those having 6 to 40 aromatic ring atoms and are R H1 Aromatic ring systems with substituted groups, and aromatic ring systems having 5 to 40 aromatic ring atoms and being R H1 Heteroaromatic ring systems with substituted groups;

[0014] R H1 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. H2 CN, Si(R) H2 )3, N(R H2 )2, P(=O)(R H2 )2, OR H2 S(=O)R H2 S(=O)2R H2 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R H1 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R H2 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R H2 C=CR H2 -、-C≡C-、Si(R H2 2. C=O, C=NR H2 -C(=O)O-, -C(=O)NR H2 -、NR H2 P(=O)(R) H2 Replace with -O-, -S-, SO or SO2;

[0015] R H2 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. H3 CN, Si(R) H3 )3, N(R H3 )2, P(=O)(R H3 )2, ORH3 S(=O)R H3 S(=O)2R H3 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R H2 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R H3 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R H3 C=CR H3 -、-C≡C-、Si(R H3 2. C=O, C=NR H3 -C(=O)O-, -C(=O)NR H3 -、NR H3 P(=O)(R) H3 Replace with -O-, -S-, SO or SO2;

[0016] R H3 In each case, the same or different and selected from H, D, F, Cl, Br, I, CN, alkyl or alkoxy groups having 1 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; wherein two or more R H3 The groups can be linked together and can form rings; and said alkyl, alkoxy, alkenyl, and alkynyl groups, aromatic ring systems, and heteroaromatic ring systems can be substituted by one or more groups selected from F and CN; and

[0017] The HOMO of the compound of formula (H) is not less than -4.72 eV, more preferably not less than -4.71 eV, wherein the HOMO is determined by the method described in Part 1 of the Examples;

[0018] and

[0019] - There are one or more layers containing a compound of formula (E) between the light-emitting layer and the cathode.

[0020]

[0021] Equation (E)

[0022] in:

[0023] A is or The dashed lines indicate the keys that connect to the rest of the expression;

[0024] Z in When the group is bonded to it, it is C and when there is no When bonded to it, the same or different in each case and selected from CR 2 and N;

[0025] X is the same or different in each case and is selected from N and CR. 4 Where at least one X is N;

[0026] Ar 1 In each case, they may be the same or different and are selected from those having 6 to 40 aromatic ring atoms and are R 3 Aromatic ring systems with substituted groups, and aromatic ring systems having 5 to 40 aromatic ring atoms and being R 3 Heteroaromatic ring systems with substituted groups;

[0027] Ar 2 In each case, they may be the same or different and are selected from those having 6 to 40 aromatic ring atoms and are R 5 Aromatic ring systems with substituted groups, and aromatic ring systems having 5 to 40 aromatic ring atoms and being R 5 Heteroaromatic ring systems with substituted groups;

[0028] R 1 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. 6 CN, Si(R) 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 S(=O)R 6 S(=O)2R 6 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R 1 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R 6 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R 6 C=CR 6 -、-C≡C-、Si(R 6 2. C=O, C=NR6 -C(=O)O-, -C(=O)NR 6 -、NR 6 P(=O)(R) 6 Replace with -O-, -S-, SO or SO2;

[0029] R 2 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. 6 CN, Si(R) 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 S(=O)R 6 S(=O)2R 6 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R 2 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R 6 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R 6 C=CR 6 -、-C≡C-、Si(R 6 2. C=O, C=NR 6 -C(=O)O-, -C(=O)NR 6 -、NR 6 P(=O)(R) 6 Replace with -O-, -S-, SO or SO2;

[0030] R 3 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. 6 CN, Si(R) 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 S(=O)R 6 S(=O)2R 6A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R 3 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R 6 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R 6 C=CR 6 -、-C≡C-、Si(R 6 2. C=O, C=NR 6 -C(=O)O-, -C(=O)NR 6 -、NR 6 P(=O)(R) 6 Replace with -O-, -S-, SO or SO2;

[0031] R 4 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. 6 CN, Si(R) 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 S(=O)R 6 S(=O)2R 6 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R 4 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R 6 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R 6 C=CR 6 -、-C≡C-、Si(R 6 2. C=O, C=NR 6 -C(=O)O-, -C(=O)NR 6 -、NR 6 P(=O)(R) 6Replace with -O-, -S-, SO or SO2;

[0032] R 5 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. 6 CN, Si(R) 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 S(=O)R 6 S(=O)2R 6 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R 5 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R 6 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R 6 C=CR 6 -、-C≡C-、Si(R 6 2. C=O, C=NR 6 -C(=O)O-, -C(=O)NR 6 -、NR 6 P(=O)(R) 6 Replace with -O-, -S-, SO or SO2;

[0033] R 6 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. 7 CN, Si(R) 7 )3, N(R 7 )2, P(=O)(R 7 )2, OR 7 S(=O)R 7 S(=O)2R 7 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R 6Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R 7 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R 7 C=CR 7 -、-C≡C-、Si(R 7 2. C=O, C=NR 7 -C(=O)O-, -C(=O)NR 7 -、NR 7 P(=O)(R) 7 Replace with -O-, -S-, SO or SO2;

[0034] R 7 In each case, the same or different and selected from H, D, F, Cl, Br, I, CN, alkyl or alkoxy groups having 1 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; wherein two or more R 7 The groups can be linked together and can form rings; and the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems can be substituted by one or more groups selected from F and CN;

[0035] n can be 0, 1, 2, 3, or 4.

[0036] When n = 0, Ar 1 The group is absent and is related to Ar in formula (E) 1 The two groups in the group bond are directly bonded to each other. In the case of n = 2, 3, or 4, there are 2, 3, or 4 consecutively bonded Ar groups. 1 Group.

[0037] In the context of this application, the expression “greater” or “higher” HOMO should be understood to mean that the value is less negative; for example, the HOMO of -5.2 eV is greater than / higher than the HOMO of -5.3 eV.

[0038] The following definitions apply to chemical groups used in this application. Unless otherwise specified, they are applicable.

[0039] In the context of this invention, aryl groups should be understood to refer to monoaromatic rings, i.e., benzene, or fused aromatic polycyclic rings, such as naphthalene, phenanthrene, or anthracene. Fused aromatic polycyclic rings in the context of this application consist of two or more monoaromatic rings fused together. Fusing between rings should be understood herein as the rings sharing at least one side. In the context of this invention, aryl groups contain 6 to 40 aromatic ring atoms. Furthermore, aryl groups do not contain any heteroatoms as aromatic ring atoms, but only carbon atoms.

[0040] In the context of this invention, a heteroaryl group should be understood to refer to a mono-heteroaromatic ring, such as pyridine, pyrimidine, or thiophene, or a fused heteroaromatic polycyclic ring, such as quinoline or carbazole. In the context of this application, a fused heteroaromatic polycyclic ring consists of two or more mono-aromatic or heteroaromatic rings fused together, wherein at least one of the aromatic and heteroaromatic rings is a heteroaromatic ring. Fusing between rings should be understood herein as the rings sharing at least one side. In the context of this invention, a heteroaryl group comprises 5 to 40 aromatic ring atoms, at least one of which is a heteroatom. The heteroatoms of the heteroaryl group are preferably selected from N, O, and S.

[0041] Each of the aryl or heteroaryl groups that can be substituted by the aforementioned groups should be understood in particular to refer to groups derived from the following substances: benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, leucine, perylene, biphenylene oxide, fluoranthene, benzo[a]anthene, benzo[a]phenanthrene, tetraphenyl, pentaphenyl, benzo[a]pyrene, furan, benzo[a]furan, isobenzo[a]furan, dibenzo[a]furan, thiophene, benzo[a]thiophene, isobenzo[a]thiophene, dibenzo[a]thiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenanthrene Azides, pyrazoles, indazoles, imidazoles, benzimidazoles, benzimidazole[1,2-a]benzimidazoles, naphthiazoles, phenanthreneimidazoles, pyridiniumimidazoles, pyraziniumimidazoles, quinoxalineimidazoles azole, benzo[ azole, naphtho azole, anthraquinone azole, phenanthrene azole, isotonic azole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, pyrazine, phenazine, naphthidine, azacarbazole, benzocarbline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3- diazole, 1,2,4- diazole, 1,2,5- diazole, 1,3,4- Diazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazolium, 1,2,4,5-tetraazine, 1,2,3,4-tetraazine, 1,2,3,5-tetraazine, purine, pteridine, indazine, and benzothiadiazole.

[0042] In the context of this invention, an aromatic ring system is a system that does not necessarily contain only aryl groups, but may additionally contain one or more non-aromatic rings fused to at least one aryl group. These non-aromatic rings contain only carbon atoms as ring atoms. Examples of groups covered by this definition are tetrahydronaphthalene, fluorene, and spirodifluorene. Furthermore, the term "aromatic ring system" includes systems consisting of two or more aromatic ring systems linked to each other by single bonds, such as biphenyl, terphenyl, 7-phenyl-2-fluorenyl, tetraphenyl, and 3,5-diphenyl-1-phenyl. In the context of this invention, an aromatic ring system contains 6 to 40 carbon atoms and has no heteroatoms. The definition of "aromatic ring system" does not include heteroaryl groups.

[0043] Heteroaromatic ring systems conform to the definition of aromatic ring systems described above, except that they must contain at least one heteroatom as a ring atom. Similar to aromatic ring systems, heteroaromatic ring systems do not necessarily contain only aryl and heteroaryl groups, but may additionally contain one or more non-aromatic rings fused to at least one aryl or heteroaryl group. These non-aromatic rings may contain only carbon atoms as ring atoms, or they may additionally contain one or more heteroatoms, wherein the heteroatoms are preferably selected from N, O, and S. An example of such a heteroaromatic ring system is benzopyranyl. Furthermore, the term "heteroaromatic ring system" should be understood to refer to a system consisting of two or more aromatic or heteroaromatic ring systems bonded together by single bonds, such as 4,6-diphenyl-2-triazineyl. In the context of this invention, heteroaromatic ring systems contain 5 to 40 ring atoms selected from carbon and heteroatoms, wherein at least one ring atom is a heteroatom. The heteroatoms in heteroaromatic ring systems are preferably selected from N, O, and S.

[0044] Therefore, the terms "heteroaromatic ring system" and "aromatic ring system" as defined in this application differ from each other in that an aromatic ring system cannot have a heteroatom as a ring atom, while a heteroaromatic ring system must have at least one heteroatom as a ring atom. This heteroatom can exist as a ring atom of a non-aromatic heterocycle or as a ring atom of an aromatic heterocycle.

[0045] According to the above definition, any aryl group is covered by the term "aromatic ring system", and any heteroaryl group is covered by the term "heteroaromatic ring system".

[0046] Aromatic ring systems having 6 to 40 aromatic ring atoms or heteroaromatic ring systems having 5 to 40 aromatic ring atoms should be particularly understood to refer to groups derived from the groups described above under aryl and heteroaromatic groups, and groups derived from biphenyl, terphenyl, tetraphenyl, fluorene, spirodifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, indofluorene, trimerin, isotrimerin, spirotrimerin, spiroisotrimerin, indocarbazole, or combinations thereof.

[0047] In the context of this invention, the individual hydrogen atoms or CH2 groups may also be replaced by straight-chain alkyl groups having 1 to 20 carbon atoms and branched or cyclic alkyl groups having 3 to 20 carbon atoms and alkenyl or alkynyl groups having 2 to 40 carbon atoms, as mentioned above under the definition of groups. Preferably, this should be understood to refer to methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl... The following groups are included: yl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, 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, penynyl, hexynyl, or ocynyl groups.

[0048] Some of the hydrogen atoms or CH2 groups may be replaced by groups mentioned under the above-described group definition. Alkoxy or thioalkyl groups having 1 to 20 carbon atoms are preferably understood to be 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, 2,2,2-trifluoroethoxy, methylthio, ethylthio, n-propoxy Thioyl, isopropylthioyl, n-butylthioyl, isobutylthioyl, sec-butylthioyl, tert-butylthioyl, n-pentylthioyl, sec-pentylthioyl, n-hexylthioyl, cyclohexylthioyl, n-heptylthioyl, cycloheptylthioyl, n-octylthioyl, cyclooctylthioyl, 2-ethylhexylthioyl, trifluoromethylthioyl, pentafluoroethylthioyl, 2,2,2-trifluoroethylthioyl, ethylenethioyl, propylenethioyl, butenethioyl, pentenethioyl, cyclopentenethioyl, hexenethioyl, cyclohexenethioyl, hepenethioyl, cycloheptenethioyl, octenenethioyl, cyclooctenenethioyl, ethynylthioyl, propynylthioyl, butynylthioyl, pentynylthioyl, hexynylthioyl, hepynylthioyl, or octyynylthioyl.

[0049] In the context of this application, the phrase "two or more groups together can form a ring" should be understood to mean, in particular, that the two groups are connected to each other by chemical bonds. However, the above phrase should also be understood to mean that if one of the two groups is hydrogen, the second group binds to the bonding position of the hydrogen atom, thereby forming a ring.

[0050] The compound of formula (H) preferably has a HOMO of not less than -4.72 eV and not more than -4.55 eV. The HOMO is measured as described in Part 1 of the Examples.

[0051] Furthermore, the compound of formula (H) preferably has 2*10 -4 cm 2 / Vs to 8*10 -4 cm 2 / Vs, Preferred 3*10 -4 cm 2 / Vs to 6*10 -4 cm 2 / Vs hole mobility. Hole mobility is measured as described in section 2) of the example.

[0052] Preferably, the preferred values ​​for hole mobility and the preferred values ​​for HOMO appear in combination in the compound of formula (H).

[0053] In compounds of formula (H), at least one Ar is preferred. H1 Groups, and more preferably at least two Ar groups. H1 The group is selected from those having 6 to 40 aromatic ring atoms and being R H1 Aromatic ring systems with substituted groups.

[0054] Preferably, Ar H1 In each case, the groups are the same or different and selected from phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, fluorenyl, especially 9,9'-dimethylfluorenyl and 9,9'-diphenylfluorenyl, benzo[fluorenyl], spirodifluorenyl, indo[fluorenyl], dibenzofuranyl, dibenzothiopheneyl, carbazolyl, benzofuranyl, benzothiopheneyl, benzofused dibenzofuranyl, benzofused dibenzothiopheneyl, naphthyl-substituted phenyl, fluorenyl-substituted phenyl, spirodifluorenyl-substituted phenyl, dibenzofuranyl-substituted phenyl, dibenzothiopheneyl-substituted phenyl, carbazolyl-substituted phenyl, pyridyl-substituted phenyl, pyrimidinyl-substituted phenyl, and triazinel-substituted phenyl, each group being R H1 Group substitution.

[0055] Preferably, at least one Ar H1 Groups, including R that substituted for them H1The group includes a spirofluorenyl or fluorenyl group, more preferably a 2-spirofluorenyl or 2-fluorenyl group. More preferably, at least one Ar H1 The groups are selected from spirofluorenyl and fluorenyl, and each group is coated with R. H1 Group substitution, more preferably selected from R H1 A spirodifluorene group substituted with a 2-spirodifluorene group. Preferably, 2-spirodifluorene and 2-fluorene groups are used, each group being substituted with R. H1 Group substitution.

[0056] Preferably, at least one R is present in the compound of formula (H). H1 Especially with Ar H1 The spirodifluorenyl group or fluorenyl group is bonded and selected from those having 1 to 20 carbon atoms and being R H2 A straight-chain alkyl group substituted with a radical, having 3 to 20 carbon atoms and being R H2 Branched or cyclic alkyl groups substituted with groups and those having 6 to 40 aromatic ring atoms and being R H2 R of group-substituted aromatic ring systems H1 More preferably, 1, 2, 3, or 4 identical or different Rs H1 The group present in the compound of formula (H) is selected from those having 1 to 20 carbon atoms and being R H2 A straight-chain alkyl group substituted with a radical, having 3 to 20 carbon atoms and being R H2 Branched or cyclic alkyl groups substituted with groups, and groups having 6 to 40 aromatic ring atoms and being R H2 Aromatic ring systems with substituted groups, and the remaining R H1 The radical is H.

[0057] R H1 Preferably, they are the same or different in each case and are selected from H, D, F, CN, Si(R) H2 )3, N(R H2 )2, a straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, an aromatic ring system having 6 to 40 aromatic ring atoms, and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein the alkyl and alkoxy groups, the aromatic ring system, and the heteroaromatic ring system are each R H2 Group substitution; and one or more CH2 groups of said alkyl or alkoxy groups can be -C≡C-, -R H2 C=CR H2 -、Si(R H2 2. C=O, C=NR H2 -NR H2 -, -O-, -S-, -C(=O)O- or -C(=O)NR H2- Instead. More preferably, R H1 In each case, the same or different and selected from H, D, F, CN, are straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, wherein the alkyl group, the aromatic ring system, and the heteroaromatic ring system are each R H2 Group substitution. Most preferably, R H1 In each case, the same or different groups are selected from straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, and aromatic ring systems having 6 to 40 aromatic ring atoms, wherein the alkyl groups and the aromatic ring systems are each R H2 Group substitution.

[0058] R H2 Preferably, in each case, the same or different and selected from H, D, F, CN, are straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, wherein the alkyl group, the aromatic ring system, and the heteroaromatic ring system are each R H3 Group substitution. More preferably, R H2 In each case, the same or different and selected from H, a straight-chain alkyl group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, and an aromatic ring system having 6 to 40 aromatic ring atoms, wherein the alkyl group and the aromatic ring system are each R H3 Group substitution.

[0059] R H3 Preferably, in each case the same or different and selected from H, D, alkyl groups having 1 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms.

[0060] Preferred embodiments of compounds of formula (H) conform to formula (H-1) or (H-2).

[0061]

[0062] Equation (H-1)

[0063]

[0064] Equation (H-2)

[0065] Where m = 0, 1, 2 or 3, the present groups are as defined above and preferably correspond to the preferred embodiments specified above, and wherein the spirodifluorenyl group, fluorenyl group and optionally present phenyl group in the formula are R in each unoccupied position. H1 Group substitution. Of the two formulas, formula (H-1) is particularly preferred. Preferably, Ar in the above formula... H1 The functional groups may be the same or different in each case and are selected from phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, fluorenyl, especially 9,9'-dimethylfluorenyl and 9,9'-diphenylfluorenyl, benzo[fluorenyl], spirodifluorenyl, indo[fluorenyl], dibenzofuranyl, dibenzothiopheneyl, carbazolyl, benzofuranyl, benzothiopheneyl, benzofused dibenzofuranyl, benzofused dibenzothiopheneyl, naphthyl-substituted phenyl, fluorenyl-substituted phenyl, spirodifluorenyl-substituted phenyl, dibenzofuranyl-substituted phenyl, dibenzothiopheneyl-substituted phenyl, carbazolyl-substituted phenyl, pyridyl-substituted phenyl, pyrimidinyl-substituted phenyl, and triazinyl-substituted phenyl, each of which is R H1 Group substitution. Furthermore, preferably, m = 0 or 1. For illustration, m = 0 indicates that the amino group and the spirodifluorenyl group or fluorenyl group are directly bonded to each other. m = 2 or 3 indicates that 2 or 3 phenyl groups are directly and continuously arranged.

[0066] Preferably, in formulas (H-1) and (H-2), there exists at least one R. H1 It is bonded to an aromatic ring of a spirodifluorenyl group or a fluorenyl group, and is selected from those having 1 to 20 carbon atoms and being R H2 A straight-chain alkyl group substituted with a radical, having 3 to 20 carbon atoms and being R H2 Branched or cyclic alkyl groups substituted with groups, and aromatic rings having 6 to 40 atoms and being R-substituted. H2 Aromatic ring systems with substituted groups.

[0067] Therefore, this application also provides an electronic device, the electronic device comprising an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, characterized in that...

[0068] -A layer containing one or more compounds of formula (H-1) or (H-2) exists between the anode and the light-emitting layer.

[0069]

[0070] Equation (H-1)

[0071]

[0072] Equation (H-2)

[0073] The spirodifluorene group, fluorene group, and optionally present benzene group can be R at each unoccupied position. H1 Group substitution, and in addition:

[0074] Ar H1 In each case, they may be the same or different and are selected from those having 6 to 40 aromatic ring atoms and are R H1 Aromatic ring systems with substituted groups, and aromatic ring systems having 5 to 40 aromatic ring atoms and being R H1 Heteroaromatic ring systems with substituted groups;

[0075] R H1 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. H2 CN, Si(R) H2 )3, N(R H2 )2, P(=O)(R H2 )2, OR H2 S(=O)R H2 S(=O)2R H2 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R H1 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R H2 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R H2 C=CR H2 -、-C≡C-、Si(R H2 2. C=O, C=NR H2 -C(=O)O-, -C(=O)NR H2 -、NR H2 P(=O)(R) H2 Replace with -O-, -S-, SO or SO2;

[0076] R H2 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. H3 CN, Si(R) H3 )3, N(R H3 )2, P(=O)(R H3 )2, OR H3 S(=O)R H3S(=O)2R H3 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R H2 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R H3 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R H3 C=CR H3 -、-C≡C-、Si(R H3 2. C=O, C=NR H3 -C(=O)O-, -C(=O)NR H3 -、NR H3 P(=O)(R) H3 Replace with -O-, -S-, SO or SO2;

[0077] R H3 In each case, the same or different and selected from H, D, F, Cl, Br, I, CN, alkyl or alkoxy groups having 1 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; wherein two or more R H3 The groups can be linked together and can form rings; and said alkyl, alkoxy, alkenyl, and alkynyl groups, aromatic ring systems, and heteroaromatic ring systems can be substituted by one or more groups selected from F and CN; and

[0078] m can be 0, 1, 2, or 3;

[0079] There exists at least one R H1 It is bonded to an aromatic ring of a spirodifluorenyl group or a fluorenyl group, and is selected from those having 1 to 20 carbon atoms and being R H2 A straight-chain alkyl group substituted with a radical, having 3 to 20 carbon atoms and being R H2 Branched or cyclic alkyl groups substituted with groups, and aromatic rings having 6 to 40 atoms and being R-substituted. H2 Aromatic ring systems with substituted groups;

[0080] and

[0081] - There are one or more layers containing a compound of formula (E) between the light-emitting layer and the cathode.

[0082]

[0083] Equation (E)

[0084] in:

[0085] A is or The dashed lines indicate the keys that connect to the rest of the expression;

[0086] Z in When the group is bonded to it, it is C and when there is no The groups bonded to them are the same or different in each case and are selected from CR. 2 and N;

[0087] X is the same or different in each case and is selected from N and CR. 4 Where at least one X is N;

[0088] Ar 1 In each case, they may be the same or different and are selected from those having 6 to 40 aromatic ring atoms and are R 3 Aromatic ring systems with substituted groups, and aromatic ring systems having 5 to 40 aromatic ring atoms and being R 3 Heteroaromatic ring systems with substituted groups;

[0089] Ar 2 In each case, they may be the same or different and are selected from those having 6 to 40 aromatic ring atoms and are R 5 Aromatic ring systems with substituted groups, and aromatic ring systems having 5 to 40 aromatic ring atoms and being R 5 Heteroaromatic ring systems with substituted groups;

[0090] R 1 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. 6 CN, Si(R) 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 S(=O)R 6 S(=O)2R 6 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R 1 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R 6Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R 6 C=CR 6 -、-C≡C-、Si(R 6 2. C=O, C=NR 6 -C(=O)O-, -C(=O)NR 6 -、NR 6 P(=O)(R) 6 Replace with -O-, -S-, SO or SO2;

[0091] R 2 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. 6 CN, Si(R) 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 S(=O)R 6 S(=O)2R 6 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R 2 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R 6 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R 6 C=CR 6 -、-C≡C-、Si(R 6 2. C=O, C=NR 6 -C(=O)O-, -C(=O)NR 6 -、NR 6 P(=O)(R) 6 Replace with -O-, -S-, SO or SO2;

[0092] R 3 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. 6 CN, Si(R) 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 S(=O)R6 S(=O)2R 6 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R 3 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R 6 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R 6 C=CR 6 -、-C≡C-、Si(R 6 2. C=O, C=NR 6 -C(=O)O-, -C(=O)NR 6 -、NR 6 P(=O)(R) 6 Replace with -O-, -S-, SO or SO2;

[0093] R 4 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. 6 CN, Si(R) 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 S(=O)R 6 S(=O)2R 6 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R 4 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R 6 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R 6 C=CR 6 -、-C≡C-、Si(R 6 2. C=O, C=NR 6 -C(=O)O-, -C(=O)NR 6 -、NR6 P(=O)(R) 6 Replace with -O-, -S-, SO or SO2;

[0094] R 5 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. 6 CN, Si(R) 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 S(=O)R 6 S(=O)2R 6 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R 5 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R 6 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R 6 C=CR 6 -、-C≡C-、Si(R 6 2. C=O, C=NR 6 -C(=O)O-, -C(=O)NR 6 -、NR 6 P(=O)(R) 6 Replace with -O-, -S-, SO or SO2;

[0095] R 6 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. 7 CN, Si(R) 7 )3, N(R 7 )2, P(=O)(R 7 )2, OR 7 S(=O)R 7 S(=O)2R 7 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R 6Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R 7 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R 7 C=CR 7 -、-C≡C-、Si(R 7 2. C=O, C=NR 7 -C(=O)O-, -C(=O)NR 7 -、NR 7 P(=O)(R) 7 Replace with -O-, -S-, SO or SO2;

[0096] R 7 In each case, the same or different and selected from H, D, F, Cl, Br, I, CN, alkyl or alkoxy groups having 1 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; wherein two or more R 7 The groups can be linked together and can form rings; and the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems can be substituted by one or more groups selected from F and CN;

[0097] n can be 0, 1, 2, 3, or 4.

[0098] For the above embodiments, it is preferred that, in addition to compounds of formula (H-1) or (H-2), other preferred embodiments of compounds of formula (H) as defined below exist in the electronic device.

[0099] More preferably, in equations (H-1) and (H-2), there are 1, 2, 3, or 4 identical or different R values. H1 Group, the R H1 The group is bonded to an aromatic ring of a spirodifluorenyl group or a fluorenyl group, and the group is selected from those having 1 to 20 carbon atoms and being R H2 A straight-chain alkyl group substituted with a radical, having 3 to 20 carbon atoms and being R H2 Branched or cyclic alkyl groups substituted with groups, and aromatic rings having 6 to 40 atoms and being R-substituted. H2 A group-substituted aromatic ring system, and the remaining R of the aromatic ring bonded to a spirodifluorenyl group or a fluorenyl group. H1 The radical is H.

[0100] The preferred embodiment of formula (H-1) conforms to the following formulas (H-1-a) to (H-1-p).

[0101]

[0102]

[0103] Where R H1-1 In each case, the same or different and selected from: straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, and aromatic ring systems having 6 to 40 aromatic ring atoms; wherein the alkyl groups and the aromatic ring systems are each R H2 Group substitution; and wherein other variables are as defined above and preferably correspond to the preferred embodiments described above, and wherein the spirodifluorene group and the phenylene group are replaced by R H1 Group substitution, the R H1 The group in each unoccupied position is preferably H. In the above formulas, formulas (H-1-a), (H-1-d), (H-1-i), and (H-1-l) are particularly preferred, especially formulas (H-1-d) and (H-1-l), especially formula (H-1-d). The phenylene group may be a p-phenylene group, a meta-phenylene group, or an o-phenylene group.

[0104] R is usually preferred. H1-1 In each case, they may be the same or different and are selected from methyl, isopropyl, tert-butyl, phenyl, biphenyl, terphenyl, tetraphenyl, and naphthyl.

[0105] The preferred embodiments of formulas (H-1) and (H-2) conform to formulas (H-1-1) and (H-2-1).

[0106]

[0107] Equation (H-1-1)

[0108]

[0109] Equation (H-2-1)

[0110] The groups and markings present therein are as defined above and preferably correspond to the preferred embodiments specified above, and wherein the spirodifluorenyl group, fluorenyl group and optionally present phenylene group in the formula are R in each unoccupied position. H1 Group substitution. Of the two formulas, formula (H-1-1) is particularly preferred.

[0111] The particularly preferred embodiment of formula (H-1-1) conforms to formulas (H-1-1-a) to (H-1-1-p).

[0112]

[0113]

[0114] Where R H1-1 In each case, the same or different groups are selected from straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, and aromatic ring systems having 6 to 40 aromatic ring atoms; wherein the alkyl groups and the aromatic ring systems are each R H2 Group substitution; and wherein other variables are as defined above and preferably correspond to the preferred embodiments described above, and wherein the spirodifluorene group and the phenylene group are replaced by R H1 Group substitution, the R H1 The group in each unoccupied position is preferably H. In the above formulas, formulas (H-1-1-a), (H-1-1-d), (H-1-1-i), and (H-1-1-l) are particularly preferred, especially formulas (H-1-1-d) and (H-1-1-l), especially formula (H-1-1-d). The phenylene group may be a p-phenylene group, a meta-phenylene group, or an o-phenylene group.

[0115] Most preferably, the compound of formula (H) conforms to one of the following formulas:

[0116]

[0117] Where R H1-1 In each case, the same or different groups are selected from straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, and aromatic ring systems having 6 to 40 aromatic ring atoms; wherein the alkyl groups and the aromatic ring systems are each R H2 Group substitution; and wherein other variables are as defined above and preferably correspond to the preferred embodiments described above, and wherein the spirodifluorene group is replaced by R H1 Group substitution, the R H1 The group is preferably H in each unoccupied position.

[0118] Preferred embodiments of the compound of formula (H) are shown in the table below:

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155] Preferably, A in the compound of formula (E-1) is The dashed key indicates the key from A to the rest of the expression.

[0156] Preferably, Z is in the absence of When the group is bonded to it, it is CR 2 When this group is bonded to it, it is C.

[0157] Preferably, in formula (E), the two X groups in the ring are N, and the third X group is CR. 4 Alternatively, all three X groups in the ring of formula (E) are N. More preferably, all three X groups in the ring of formula (E) are N.

[0158] Preferably, the The functional group conforms to the following formula:

[0159] Equation (HetAr-1)

[0160] The dashed lines represent the keys that connect to the rest of the expression.

[0161] Preferably, Ar 2 In each case, the groups may be the same or different, preferably the same, and are selected from groups derived from the following substances: benzene, cyanobenzene, biphenyl, terphenyl, naphthalene, phenanthrene, biphenylene oxide, fluorene, indofluorobenzene, indocarbazole, spirofluorene, dibenzofuran, dibenzofuran-substituted benzene, dibenzothiophene, dibenzothiophene-substituted benzene, carbazole, carbazole-substituted benzene, bisN-carbazole-substituted benzene, each of which is substituted by one or more R 5 The groups are substituted, more preferably benzene, cyanobenzene, biphenyl, terphenyl, naphthalene, phenanthrene, biphenylene oxide, dibenzofuran, dibenzofuranyl-substituted benzene, dibenzothiophene, dibenzothiopheneyl-substituted benzene, and carbazole, wherein each group is substituted by one or more R 5 Group substitution. Even more preferably, Ar 2 In each case, it is by one or more R 5 Benzene with a substituent group, wherein R 5 In this case, H and CN are particularly preferred. Unsubstituted benzene is the most preferred.

[0162] Ar 1 Preferably, the divalent groups are the same or different and selected from those derived from the following substances: benzene, biphenyl, terphenyl, naphthalene, fluorene, indole-fluorene, indole-carbazole, spirodifluorene, dibenzofuran, dibenzothiophene, and carbazole, each of which can be generated by one or more R... 3 Group substitution. Even more preferably, Ar 1 It is a divalent group derived from benzene, biphenyl, and naphthyl, each of which can be converted by one or more R... 3 Groups are substituted and preferably unsubstituted, especially p-phenylene, o-phenylene, or meta-phenylene, each of which can be substituted by one or more R groups. 3 The group is substituted and preferably unsubstituted, most preferably p-phenylene group, said group may be substituted by one or more R groups. 3 The groups are substituted, and preferably unsubstituted.

[0163] In a preferred embodiment, n is 0. In an alternative preferred embodiment, n is 1, 2, or 3, preferably 1 or 2, and more preferably 1.

[0164] Preferred -(Ar 1 ) n -groups, especially -Ar 1 -, conforms to the following formula:

[0165]

[0166]

[0167]

[0168]

[0169] The dashed lines represent the bonds that connect to the rest of the expression. The particularly preferred expression (Ar) 1 -1) to (Ar 1 -9), (Ar 1 -15) and (Ar 1 -19).

[0170] Preferably, R 1 The same or different in each case, preferably the same, and selected from H, D, F, CN, Si(R) 6 )3, a straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, an aromatic ring system having 6 to 40 aromatic ring atoms, and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein the alkyl and alkoxy groups, the aromatic ring system, and the heteroaromatic ring system are each R 6Group substitution; and one or more CH2 groups of said alkyl or alkoxy groups can be -C≡C-, -R 6 C=CR 6 -、Si(R 6 2. C=O, C=NR 6 -NR 6 -, -O-, -S-, -C(=O)O- or -C(=O)NR 6 - Instead. More preferably, R 1 In each case, the same or different, preferably the same, and selected from H, F, straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, wherein the aromatic ring system and the heteroaromatic ring system are each R 6 Group substitution. Most preferably, R 1 In each case, they may be the same or different, preferably the same, and are selected from methyl and phenyl.

[0171] Preferably, R 2 The same or different in each case and selected from H, D, F, CN, Si(R) 6 )3, a straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, an aromatic ring system having 6 to 40 aromatic ring atoms, and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein the alkyl and alkoxy groups, the aromatic ring system, and the heteroaromatic ring system are each R 6 Group substitution; and one or more CH2 groups of said alkyl or alkoxy groups can be -C≡C-, -R 6 C=CR 6 -、Si(R 6 2. C=O, C=NR 6 -NR 6 -, -O-, -S-, -C(=O)O- or -C(=O)NR 6 - Instead. More preferably, R 2 In each case, the same or different groups are selected from straight-chain alkyl groups having 1 to 20 carbon atoms, branched alkyl groups having 3 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, wherein the alkyl group, the aromatic ring system, and the heteroaromatic ring system are each R 6 Group substitution. Most preferably, R 2 It is H.

[0172] Preferably, R 3The same or different in each case and selected from H, D, F, CN, Si(R) 6 )3, a straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, an aromatic ring system having 6 to 40 aromatic ring atoms, and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein the alkyl and alkoxy groups, the aromatic ring system, and the heteroaromatic ring system are each R 6 Group substitution; and one or more CH2 groups of said alkyl or alkoxy groups can be -C≡C-, -R 6 C=CR 6 -、Si(R 6 2. C=O, C=NR 6 -NR 6 -, -O-, -S-, -C(=O)O- or -C(=O)NR 6 -replace.

[0173] Preferably, R 4 The same or different in each case and selected from H, D, F, CN, Si(R) 6 )3, a straight-chain alkyl group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, an aromatic ring system having 6 to 40 aromatic ring atoms, and a heteroaromatic ring system having 5 to 40 aromatic ring atoms, wherein the alkyl group, the aromatic ring system, and the heteroaromatic ring system are each R 6 Group substitution. More preferably, R 4 In each case, they may be the same or different and are selected from H and have 6 to 40 aromatic ring atoms and are R 6 Aromatic ring systems with substituted groups. Most preferably, R 4 In each case, they may be the same or different and are selected from H, phenyl, biphenyl, terphenyl, and naphthyl, each being R 6 Group substitution.

[0174] Preferably, R 5 The same or different in each case and selected from H, D, F, CN, Si(R) 6 )3, a straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, an aromatic ring system having 6 to 40 aromatic ring atoms, and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein the alkyl and alkoxy groups, the aromatic ring system, and the heteroaromatic ring system are each R 6 Group substitution; and one or more CH2 groups of said alkyl or alkoxy groups can be -C≡C-, -R 6 C=CR 6-、Si(R 6 2. C=O, C=NR 6 -NR 6 -, -O-, -S-, -C(=O)O- or -C(=O)NR 6 -replace.

[0175] Preferably, R 6 The same or different in each case and selected from H, D, F, CN, Si(R) 7 )3, a straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, an aromatic ring system having 6 to 40 aromatic ring atoms, and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein the alkyl and alkoxy groups, the aromatic ring system, and the heteroaromatic ring system are each R 7 Group substitution; and one or more CH2 groups of said alkyl or alkoxy groups can be -C≡C-, -R 7 C=CR 7 -、Si(R 7 2. C=O, C=NR 7 -NR 7 -, -O-, -S-, -C(=O)O- or -C(=O)NR 7 -replace.

[0176] The compound of formula (E) preferably conforms to one of the following formulas:

[0177]

[0178]

[0179] The symbols and markings present therein are as defined above, and preferably correspond to the preferred embodiments specified above. Particularly preferred for the formula is that Z is in the absence of... or When the group is bonded to it, it is CR 2 Furthermore, Z is C when bonded to this group. Preferably, R... 1 It is methyl or phenyl. Among formulas (E-1) to (E-4), formulas (E-1) and (E-2) are preferred, with formula (E-1) being particularly preferred.

[0180] The preferred embodiments of formulas (E-1) to (E-4) conform to the formulas shown below:

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187] The symbols and markings present therein are as defined above, and preferably correspond to the preferred embodiments specified above. -(R 2 )3 or -(R 2 )4 represents the presence of three or four R on the benzene ring under discussion. 2 A group, that is, an R group at each unoccupied position on the benzene ring in question. 2 Group. Preferably, for the formula, Ar 1 Ar 2 R 1 and R 2 The above-described preferred embodiments of the group are applicable. Particularly preferred is that, in the above formula, Ar... 1 It is phenyl or biphenyl, especially phenyl, Ar 2 It is a phenyl or biphenyl, R 1 It is methyl or phenyl, and R 2 It is H.

[0188] Of the above formulas (E-1-1) to (E-4-4), formulas (E-1-1) to (E-1-4) and (E-2-1) to (E-2-4) are preferred, especially formulas (E-1-1) to (E-1-4). Of the formulas (E-1-1) to (E-1-4) and (E-2-1) to (E-2-4), formulas (E-1-2), (E-1-4), (E-2-2), and (E-2-4) are preferred, especially formulas (E-1-2) and (E-1-4).

[0189] For equations (E-1-1) to (E-4-4), the preferred option is...

[0190] -Ar 1 The same or different divalent groups selected from those derived from the following substances: benzene, biphenyl, terphenyl, naphthalene, fluorene, indole-fluorene, indole-carbazole, spirodifluorene, dibenzofuran, dibenzothiophene, and carbazole, each of which can be substituted by one or more R... 3 Group substitution;

[0191] -Ar 2In each case, the groups may be the same or different, preferably the same, and are selected from groups derived from the following substances: benzene, cyanobenzene, biphenyl, terphenyl, naphthalene, phenanthrene, biphenylene oxide, fluorene, indofluorobenzene, indocarbazole, spirofluorene, dibenzofuran, dibenzofuran-substituted benzene, dibenzothiophene, dibenzothiophene-substituted benzene, carbazole, carbazole-substituted benzene, bisN-carbazole-substituted benzene, each of which is substituted by one or more R 5 Group substitution;

[0192] -R 1 In each case, the same or different groups are selected from straight-chain alkyl groups having 1 to 20 carbon atoms, branched alkyl groups having 3 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, wherein the alkyl group, the aromatic ring system, and the heteroaromatic ring system are each R 6 Group substitution;

[0193] -R 2 In each case, the aromatic ring systems are the same or different and are selected from H and F, having 6 to 40 aromatic ring atoms, and the heteroaromatic ring systems having 5 to 40 aromatic ring atoms; wherein the aromatic ring system and the heteroaromatic ring system are each R 6 Group substitution.

[0194] Preferred embodiments of the compound of formula (E) are selected from the following compounds:

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228] The layer containing the compound of formula (H) is preferably a hole transport layer. The compound of formula (H) may exist in the layer in its pure form or in a mixture with another hole transport material, or in a mixture with a p-type dopant. The other hole transport material here is preferably selected from triarylamines, more preferably monotriarylamines, and especially from the preferred hole transport materials explicitly described below.

[0229] The p-type dopant used according to the present invention is preferably an organic electron acceptor compound capable of oxidizing one or more other compounds in the mixture.

[0230] Particularly preferred p-type dopants are quinone dimethane compounds, azidoindofluorene dione, azidothione, azidotriphenylide, I2, metal halides, preferably transition metal halides, metal oxides, preferably metal oxides containing at least one transition metal or Group 3 metal, and transition metal complexes, preferably complexes of Cu, Co, Ni, Pd, and Pt with ligands containing at least one oxygen atom as a bonding site. Transition metal oxides are further preferred as dopants, preferably oxides of rhenium, molybdenum, and tungsten, more preferably Re2O7, MoO3, WO3, and ReO3. Bismuth (III) oxidation state complexes are even more preferred, particularly bismuth (III) complexes having electron-deficient ligands, and more particularly carboxylate ligands.

[0231] The p-type dopant is preferably distributed substantially uniformly in the p-type doped layer. This can be achieved, for example, by co-evaporation of the p-type dopant and the hole transport material matrix. The p-type dopant is preferably present in the p-type doped layer at a ratio of 1% to 10%.

[0232] Preferred p-type dopants, especially the following compounds:

[0233]

[0234]

[0235] In addition to the layer containing the compound of formula (H), the electronic device may also include one or more additional hole transport layers, hole injection layers, and electron blocking layers. Preferably, the electronic device has the following layer configuration, wherein a hole injection layer is present directly adjacent to the anode and disposed next to the layer containing the compound of formula (H), and an electron blocking layer is present directly adjacent to the light-emitting layer on the anode side.

[0236] The hole injection layer preferably comprises a hole transport material, preferably a triarylamine, more preferably a compound selected from specific embodiments of the hole transport material specified below, and a p-type dopant as defined above. In a preferred embodiment, the hole injection layer comprises a compound of formula (H) as defined above and a p-type dopant as defined above.

[0237] In another preferred embodiment, the hole-injection layer comprises a hexaazatriphenylide derivative as described in US 2007 / 0092755, or another highly electron-deficient and / or Lewis acidic compound, in pure form, i.e., not mixed with another compound. Examples of such compounds include bismuth complexes, especially Bi(III) complexes, especially Bi(III) carboxylates, such as the aforementioned compound D-14.

[0238] Preferably, the electronic device includes an electron blocking layer directly adjacent to the light-emitting layer on the anode side. The electron blocking layer preferably comprises a compound selected from triarylamines containing one or more fluorenyl or spirodifluorenyl groups.

[0239] Compounds of formula (EBM) are particularly preferred.

[0240]

[0241] Formula (EBM)

[0242] in:

[0243] Y is the same or different in each case and is selected from O, S, and NR. EBM1 ;

[0244] Ar 3 In each case, they may be the same or different and are selected from aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, each ring system being R EBM1 Group substitution;

[0245] k is 1, 2, or 3;

[0246] i is the same or different in each case and is selected from 0, 1, 2 and 3;

[0247] And the formula is R in each unoccupied position. EBM1 Group substitution, in which

[0248] R EBM1 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. EBM2 CN, Si(R) EBM2 )3, N(R EBM2 )2, P(=O)(R EBM2 )2, OR EBM2 S(=O)R EBM2 S(=O)2R EBM2 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R EBM1 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R EBM2Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R EBM2 C=CR EBM2 -、-C≡C-、Si(R EBM2 2. C=O, C=NR EBM2 -C(=O)O-, -C(=O)NR EBM2 -、NR EBM2 P(=O)(R) EBM2 Replace with -O-, -S-, SO or SO2;

[0249] R EBM2 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. EBM3 CN, Si(R) EBM3 )3, N(R EBM3 )2, P(=O)(R EBM3 )2, OR EBM3 S(=O)R EBM3 S(=O)2R EBM3 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R EBM2 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R EBM3 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R EBM3 C=CR EBM3 -、-C≡C-、Si(R EBM3 2. C=O, C=NR EBM3 -C(=O)O-, -C(=O)NR EBM3 -、NR EBM3 P(=O)(R) EBM3 Replace with -O-, -S-, SO or SO2;

[0250] R EBM3 In each case, the same or different and selected from H, D, F, Cl, Br, I, CN, alkyl or alkoxy groups having 1 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; wherein two or more R EBM3The groups can be linked together and can form rings; and the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems can be substituted by one or more groups selected from F and CN.

[0251] Preferably, in formula (EBM), Y is the same or different in each case and is selected from O and S, more preferably O. Further preferably, k is 1 or 2. Further preferably, i is the same or different in each case and is selected from 1 and 2, more preferably 1.

[0252] Preferably, at least one Ar in formula (EBM) 3 More preferably, exactly one Ar in the EBM (Electronic Array Model) 3 The phenyl group selected from phenyl, biphenyl, terphenyl, fluorenyl-substituted phenyl and spirodifluorenyl-substituted phenyl, each being R EBM1 Group substitution.

[0253] The preferred embodiment of formula (EBM) conforms to the following formula:

[0254]

[0255] And the formula is R in each unoccupied position. EBM1 Group substitution. In the above formulas (EBM-1) to (EBM-4), preferably, the fluorenyl or spirodifluorenyl group is bonded at position 1 or 4, more preferably at position 4:

[0256]

[0257] Compounds used as hole transport materials in electronic devices include, in particular, indoxorubicinamine derivatives, amine derivatives, hexaazatriphenylide derivatives, amine derivatives with fused aromatic systems, monobenzo[a]indoxorubicinamine, dibenzo[a]indoxorubicinamine, spirodifluoreneamine, fluoreneamine, spirodibenzopyranamine, dihydroacridine derivatives, spirodibenzofuran and spirodibenzothiophene, phenanthrene diarylamine, spirotribenzotropeneone, spirodifluorene with m-phenylenediamine group, spirodiacridine, xanthondiarylamine, and 9,10-dihydroanthraspirone with diarylamino group.

[0258] Compounds suitable for use as matrix materials in electronic devices or OLEDs, particularly hole injection layers, hole transport layers, and / or electron blocking layers, or as matrix materials in light-emitting layers, especially in light-emitting layers containing one or more phosphorescent emitters, are shown in the table below:

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265] Compounds HT-1 to HT-77 are generally well suited for the aforementioned uses in OLEDs of any design and composition, and not just in the OLEDs according to this application. Methods for preparing these compounds, as well as further relevant disclosures relating to the uses of these compounds, are disclosed in the published specification, each referenced in parentheses in the tables below the respective compounds. The compounds exhibit good performance data in OLEDs, particularly good lifetime and good efficiency.

[0266] The layer containing the compound of formula (E) is preferably an electron transport layer. In a preferred embodiment, the layer containing the compound of formula (E) is not directly adjacent to the light-emitting layer; alternatively, a hole-blocking layer directly adjacent to the light-emitting layer exists between the light-emitting layer and the layer containing the compound of formula (E).

[0267] In a preferred embodiment, the electronic device includes a hole-blocking layer directly adjacent to the light-emitting layer and an electron transport layer between the light-emitting layer and the cathode. In another preferred embodiment, an electron injection layer exists between the electron transport layer and the cathode, directly adjacent to the cathode. In an alternative preferred embodiment, no such electron injection layer is present. In this case, the electron transport layer preferably includes an alkali metal salt, more preferably a lithium salt, in addition to an electron transport material. The alkali metal salt is preferably a salt formed with an organic anion, more preferably an 8-hydroxyquinoline salt. Most preferably, the alkali metal salt is lithium 8-hydroxyquinoline.

[0268] The electron transport layer of the electronic device preferably contains an E-type compound.

[0269] The hole-blocking layer is preferably an inclusion compound (HBM).

[0270]

[0271] Formula (HBM)

[0272] in:

[0273] Ar HBM1 In each case, they may be the same or different and are selected from those having 6 to 40 aromatic ring atoms and are R HBM1 Aromatic ring systems with substituted groups, and those selected from those having 5 to 40 aromatic ring atoms and being R-substituted. HBM1 Heteroaromatic ring systems with substituted groups;

[0274] p is 0 or 1, where when p = 0, the nitrogen atom and the Q group are directly bonded to each other;

[0275] Q is selected from those having 5 to 40 aromatic ring atoms (containing at least one nitrogen atom as an aromatic ring atom) and is R HBM2 Electron-deficient heteroaryl groups substituted by radicals;

[0276] R HBM1 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. HBM3 CN, Si(R) HBM3 )3, N(R HBM3 )2, P(=O)(R HBM3 )2, OR HBM3 S(=O)R HBM3 S(=O)2R HBM3 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R HBM1 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R HBM3 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R HBM3 C=CR HBM3 -、-C≡C-、Si(R HBM3 2. C=O, C=NR HBM3 -C(=O)O-, -C(=O)NR HBM3 -、NR HBM3 P(=O)(R) HBM3 Replace with -O-, -S-, SO or SO2;

[0277] R HBM2 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. HBM3 CN, Si(R) HBM3 )3, N(R HBM3 )2, P(=O)(R HBM3 )2, OR HBM3 S(=O)R HBM3 S(=O)2R HBM3A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R HBM2 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R HBM3 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R HBM3 C=CR HBM3 -、-C≡C-、Si(R HBM3 2. C=O, C=NR HBM3 -C(=O)O-, -C(=O)NR HBM3 -、NR HBM3 P(=O)(R) HBM3 Replace with -O-, -S-, SO or SO2;

[0278] R HBM3 In each case, the same or different and selected from H, D, F, Cl, Br, I, CN, alkyl or alkoxy groups having 1 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; wherein two or more R HBM3 The groups can be linked together and can form rings; and the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems can be substituted by one or more groups selected from F and CN;

[0279] And the spiral difluorene is R in each unoccupied position. HBM1 Group substitution.

[0280] Preferably, Ar HBM1 The divalent groups are selected from those derived from the following substances: benzene, biphenyl, terphenyl, naphthalene, fluorene, indo[a]fluorene, indo[a]carbazole, spirodifluorene, dibenzofuran, dibenzothiophene, and carbazole, each of which can be derived from one or more R... HBM1 Group substitution. Even more preferably, Ar HBM1 It is a divalent group derived from benzene, biphenyl, and naphthyl, each of which can be converted by one or more R... HBM1 The divalent group is substituted and preferably unsubstituted, particularly p-phenylene, o-phenylene, or meta-phenylene, each of which can be substituted by one or more R groups. HBM1 Group substitution and preferably unsubstituted, most preferably can be substituted by one or more R groups.HBM1 The group is substituted, and preferably unsubstituted p-phenylene group.

[0281] Preferred Ar HBM1 The group corresponds to the Ar formula above. 1 -1 to Ar 1 -75 group.

[0282] Preferably, p = 0.

[0283] Preferably, Q is selected from a group comprising at least one heteroaromatic six-membered ring containing at least one nitrogen atom as a ring atom, or from a group comprising at least one aromatic five-membered ring containing at least two nitrogen atoms as ring atoms. The aforementioned six-membered or five-membered ring can be fused to another ring. The aforementioned heteroaromatic six-membered ring containing at least one nitrogen atom as a ring atom is particularly selected from azazines.

[0284] More preferably, Q is selected from triazine, pyrimidine, and quinazoline, each being reacted by R. HBM2 Group substitution. Even more preferably, Q is selected from triazine and pyrimidine, each replaced by R. HBM2 Group substitution. Most preferably, Q is a triazine, and in each case is replaced by R. HBM2 Group substitution, wherein R HBM2 In this case, the group is preferably selected from aromatic ring systems having 6 to 40 aromatic ring atoms, especially phenyl, naphthyl, biphenyl, terphenyl, tetraphenyl and fluorenyl.

[0285] Preferred embodiments of the Q group are selected from formulas (Q-1) to (Q-5).

[0286]

[0287] The dashed lines indicate the keys that connect to the rest of the formula, and R in formulas (Q-1) to (Q-5) HBM2 Preferably, the aromatic ring system is selected from aromatic ring systems having 6 to 40 aromatic ring atoms, especially phenyl, naphthyl, biphenyl, terphenyl, tetraphenyl and fluorenyl. Among formulas (Q-1) to (Q-5), formulas (Q-1) to (Q-3) are preferred, and formula (Q-1) is the most preferred.

[0288] The preferred embodiments of formula (HBM) conform to the following formulas (HBM-1) to (HBM-4):

[0289]

[0290] Among them, spirodifluorene is R in each unoccupied position. HBM1 The groups are substituted and preferably unsubstituted, and other variables are as defined above and preferably correspond to the preferred embodiments described above. In the above formula, formula (HBM-1) is particularly preferred.

[0291] Preferred compounds of formula (HBM) are shown in the table below:

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304] Preferably, the electron transport layer containing the compound of formula (E) further contains an alkali metal salt, more preferably a lithium salt. The alkali metal salt is preferably a salt formed with an organic anion, more preferably an 8-hydroxyquinoline salt. Most preferably, the alkali metal salt is lithium 8-hydroxyquinoline (LiQ).

[0305] The electron-injected layer preferably comprises one or more compounds, preferably a compound selected from LiQ, Yb, LiF, and CsF. The electron-injected layer preferably has a thickness of 0.5 nm to 5 nm, especially 1 nm to 3 nm.

[0306] The material used for the layer between the light-emitting layer and the cathode, especially for the electron transport layer, can be any material used as an electron transport material in the corresponding device according to existing technology. Particularly suitable are aluminum complexes such as Alq3, zirconium complexes such as Zrq4, lithium complexes such as Liq, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, and quinoline derivatives. Diazole derivatives, aromatic ketones, lactams, boranes, phosphazacyclopentane derivatives, and phosphine oxide derivatives.

[0307] Preferred embodiments of such compounds are shown in the table below:

[0308]

[0309]

[0310] The electronic device is preferably selected from organic integrated circuits (OIC), organic field-effect transistors (OFET), organic thin-film transistors (OTFT), organic light-emitting transistors (OLET), organic solar cells (OSC), organic optical detectors, organic photosensors, organic field quenching devices (OFQD), organic light-emitting electrochemical cells (OLEC), organic laser diodes (O-lasers), and more preferably organic electroluminescent devices (OLED).

[0311] In addition to the cathode, anode, light-emitting layer, layer containing a compound of formula (H), and layer containing a compound of formula (E), the electronic device may include additional layers. These are, for example, selected in each case from one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, electron blocking layers, exciton blocking layers, intermediate layers, charge generation layers, and / or organic or inorganic p / n junctions.

[0312] A preferred configuration of the electronic device is as follows:

[0313] -anode

[0314] - Hole injection layer

[0315] - The layer containing the compound of formula (H) serves as a hole transport layer.

[0316] -Optional additional hole transport layer

[0317] - Electron blocking layer

[0318] -Emitting layer

[0319] - Hole barrier layer

[0320] - The layer containing the compound of formula (E) serves as an electron transport layer.

[0321] -Optional additional electron transport layer

[0322] -Optional electron injection layer

[0323] -cathode.

[0324] The light-emitting layer of the device can be a fluorescent or phosphorescent light-emitting layer. Preferably, the light-emitting layer is a fluorescent light-emitting layer, and more preferably a blue fluorescent light-emitting layer. In the fluorescent light-emitting layer, the light emitter is preferably a singlet light emitter, i.e., a compound that emits light from an excited singlet state during device operation. In the phosphorescent light-emitting layer, the light emitter is preferably a triplet light emitter, i.e., a compound that emits light from an excited triplet state or from a state with a higher spin quantum number, such as a quintet state, during device operation.

[0325] In a preferred embodiment, the fluorescent emitting layer used is a blue fluorescent layer.

[0326] In a preferred embodiment, the phosphorescent layer used is a green or red phosphorescent layer.

[0327] Suitable phosphorescent emitters are especially compounds that emit light when properly excited, preferably in the visible light region, and also 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. Compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium are preferred as phosphorescent emitters, especially compounds containing iridium, platinum, or copper.

[0328] Generally, all phosphorescent complexes used in phosphorescent OLEDs according to the prior art, as well as all phosphorescent complexes known to those skilled in the art in the field of organic electroluminescent devices, are applicable to the devices of the present invention.

[0329] Preferred fluorescent compounds are selected from the arylamine category. In the context of this invention, arylamines or aromatic amines should be understood as compounds containing three substituted or unsubstituted aromatic or heteroaromatic ring systems directly bonded to nitrogen. Preferably, at least one of these aromatic or heteroaromatic ring systems is a fused ring system, more preferably having at least 14 aromatic ring atoms. Preferred examples of these are aromatic anthraceneamines, aromatic anthracene diamines, aromatic pyreneamines, aromatic pyrene diamines, aromatic pyrimethamines, or aromatic pyrimethamines.

[0330] Aromatic anthracene amines should be understood as compounds in which a diaryl amino group is directly bonded to an anthracene group, preferably at the 9-position. Aromatic anthracene diamines should be understood as compounds in which two diaryl amino groups are directly bonded to an anthracene group, preferably at the 9- and 10-positions. Aromatic pyrene amines, pyrene diamines, pyrine amines, and pyrine diamines are similarly defined, wherein the diaryl amino group is preferably bonded to pyrene at the 1-position or at the 1- and 6-positions.

[0331] Also preferred luminescent compounds are indene fluoreneamine or indene fluorene diamine, benzo[a]indene fluoreneamine or benzo[a]indene fluorene diamine, and dibenzo[a]indene fluoreneamine or dibenzo[a]indene fluorene diamine, as well as indene fluorene derivatives having fused aryl groups. Pyrene arylamines are also preferred. Benzo[a]indene fluoreneamine, benzo[a]fluoreneamine, extended benzo[a]indene, and phenanthrene are also preferred. Azides and fluorene derivatives linked to furan or thiophene units.

[0332] Preferred compounds for use as fluorescent emitters are shown in the table below:

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340] In a preferred embodiment, the light-emitting layer of the electronic device comprises exactly one matrix compound. The matrix compound should be understood to refer to a compound that is not a light-emitting compound. This embodiment is particularly preferred in the case of a fluorescent light-emitting layer.

[0341] In an alternative preferred embodiment, the light-emitting layer of the electronic device comprises exactly two or more, preferably exactly two, matrix compounds. This embodiment is also referred to as a mixed matrix system and is particularly preferred in the case of phosphorescent light-emitting layers.

[0342] In the case of a phosphorescent luminescent layer, the total proportion of all matrix materials is preferably between 50.0% and 99.9%, more preferably between 80.0% and 99.5%, and most preferably between 85.0% and 97.0%.

[0343] The percentages expressed as % should be understood here to refer to the percentage expressed as volume % in the case of a layer applied from the gas phase, and the percentage expressed as weight % in the case of a layer applied from a solution.

[0344] Accordingly, the proportion of phosphorescent compounds is preferably between 0.1% and 50.0%, more preferably between 0.5% and 20.0%, and most preferably between 3.0% and 15.0%.

[0345] In the case of a fluorescent luminescent layer, the total proportion of all matrix materials is preferably between 50.0% and 99.9%, more preferably between 80.0% and 99.5%, and most preferably between 90.0% and 99.0%.

[0346] Accordingly, the proportion of fluorescent luminescent compounds is between 0.1% and 50.0%, preferably between 0.5% and 20.0%, and more preferably between 1.0% and 10.0%.

[0347] The hybrid matrix system preferably comprises two or three different matrix materials, more preferably two different matrix materials. Preferably, in this case, one of the two materials is a material having properties including hole transport characteristics, while the other material is a material having properties including electron transport characteristics. Other matrix materials that may be present in the hybrid matrix system are compounds with a large energy difference between HOMO and LUMO (wide bandgap materials). The two different matrix materials may be present in a ratio of 1:50 to 1:1, preferably 1:20 to 1:1, more preferably 1:10 to 1:1, and most preferably 1:4 to 1:1. The hybrid matrix system is preferably used in phosphorescent organic light-emitting devices.

[0348] Preferred matrix materials for fluorescent compounds are selected from the following categories: oligoarylene groups (e.g., 2,2',7,7'-tetraphenylspirodifluorene), especially oligoarylene groups containing fused aromatic groups, oligoarylene vinyl groups, multi-legged metal complexes, hole-conducting compounds, electron-conducting compounds, especially ketones, phosphine oxides, and sulfoxides; transisomers, boric acid derivatives, and benzanthracene. Particularly preferred matrix materials are selected from the following categories: oligoarylene groups including naphthalene, anthracene, benzanthracene, and / or pyrene, or transisomers of these compounds, oligoarylene vinyl groups, ketones, phosphine oxides, and sulfoxides. Very particularly preferred matrix materials are selected from the following categories: oligoarylene groups including anthracene, benzanthracene, benzo[a]phenanthrene, and / or pyrene, or transisomers of these compounds. In the context of this invention, oligoarylene groups should be understood to refer to compounds in which at least three aryl or arylene groups are bonded to each other.

[0349] Preferred matrix materials for fluorescent compounds are shown in the table below:

[0350]

[0351]

[0352]

[0353]

[0354] Preferred matrix materials for phosphorescent emitters are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, triarylamines, carbazole derivatives such as CBP (N,N-biscarbazole biphenyl), indobenzocarbazole derivatives, indobenzocarbazole derivatives, azacarbazole derivatives, bipolar matrix materials, silanes, borazine or borate esters, triazine derivatives, zinc complexes, diazacyclopentane or tetrazacyclopentane derivatives, phosphazacyclopentane derivatives, bridged carbazole derivatives, biphenylide derivatives, or lactams.

[0355] In a preferred embodiment, the electronic device includes exactly one light-emitting layer.

[0356] In an alternative preferred embodiment, the electronic device comprises multiple light-emitting layers, preferably two, three, or four. This is particularly preferred for electronic devices that emit white light.

[0357] Preferably, the emitting layer in this case has a total of multiple emission peaks between 380 nm and 750 nm, resulting in white light emission; in other words, multiple luminescent compounds that can fluoresce or phosphore and emit blue, green, yellow, orange, or red light are used in the emitting layer. A three-layer system is particularly preferred, i.e., a system with three emitting layers, wherein in each case one of the three layers exhibits blue emission, in each case one of the three layers exhibits green emission, and in each case one of the three layers exhibits orange or red emission. In an alternative embodiment, to produce white light, a single luminescent compound emitting light over a wide wavelength range may be used instead of luminescent compounds emitting multiple colors.

[0358] In a preferred embodiment of the invention, the electronic device comprises two or three, preferably three, identical or different, stacked layer sequences, wherein each layer sequence comprises the following layers: a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, and an electron transport layer, and wherein at least one, preferably all, of the layer sequences comprises at least one light-emitting layer, a layer containing a compound of formula (E), and a layer containing a compound of formula (H).

[0359] Preferably, in each case, a double layer consisting of adjacent n-CGLs and p-CGLs is arranged between the layer sequences, wherein the n-CGLs are disposed on the anode side and the p-CGLs are correspondingly disposed on the cathode side. Here, CGL stands for charge generation layer. Materials used for such layers are known to those skilled in the art. Preferably, p-type doped amines are used in the p-CGLs, and more preferably, materials selected from hole transport materials of the preferred structural categories described above.

[0360] The preferred cathode of the electronic device is a metal with low work function, a metal alloy or multilayer structure composed of multiple metals, such as alkaline earth metals, alkali metals, main group metals or lanthanides (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Also suitable are alloys composed of alkali metals or alkaline earth metals and silver, such as alloys composed of magnesium and silver. In the case of a multilayer structure, other metals with relatively high work function, such as Ag or Al, may also be used in addition to the aforementioned metals. In this case, combinations of metals, such as Ca / Ag, Mg / Ag, or Ba / Ag, are typically used. It is also preferable to introduce a thin interlayer of material with a high dielectric constant between the metal cathode and the organic semiconductor. Examples of materials suitable for this purpose are alkali metal fluorides or alkaline earth metal fluorides, but corresponding oxides or carbonates (e.g., LiF, Li₂O, BaF₂, MgO, NaF, CsF, Cs₂CO₃, etc.) may also be used for this purpose. Furthermore, lithium hydroxyquinoline (LiQ) is used for this purpose. The thickness of this layer is preferably between 0.5 nm and 5 nm.

[0361] The preferred anode is a material with a high work function. Preferably, the anode has a work function greater than 4.5 eV relative to vacuum. Firstly, metals with high redox potentials, such as Ag, Pt, or Au, are suitable for this purpose. Secondly, metal / metal oxide electrodes (e.g., Al / Ni / NiO) are also preferred. x Al / PtO x For some applications, at least one electrode must be transparent or partially transparent to enable irradiation of organic materials (organic solar cells) or light emission (OLEDs, O-lasers). The preferred anode material here is a conductive mixed metal oxide. Indium tin oxide (ITO) or zinc indium oxide (IZO) is particularly preferred. Furthermore, conductive doped organic materials, especially conductive doped polymers, are preferred. Additionally, the anode may also consist of two or more layers, for example, an inner layer of ITO and an outer layer of a metal oxide (preferably tungsten oxide, molybdenum oxide, or vanadium oxide).

[0362] In production, the device is appropriately structured (depending on the application), with contact connections and finally sealed to eliminate the destructive effects of water and air.

[0363] In a preferred embodiment, the electronic device is characterized by applying one or more layers via a sublimation process. In this case, in a vacuum sublimation system, at less than 10 -5 millibars, preferably less than 10 -6 The material is applied via vapor deposition at an initial pressure of millibars. However, in this case, the initial pressure can also be lower, for example, less than 10. -7 millibar.

[0364] Also preferred are the electronic devices described below, characterized by applying one or more layers by OVPD (organic vapor deposition) or by means of carrier gas sublimation. In this case, at 10 -5 The material is applied at a pressure of millibar to 1 bar. A special case of this method is OVJP (Organic Vapor Jet Printing), in which the material is applied directly through a nozzle and is therefore structured.

[0365] Furthermore, a preferred electronic device is characterized by producing one or more layers from a solution, for example by spin coating, or by any printing method such as screen printing, flexographic printing, nozzle printing or offset printing, but more preferably by LITI (photoinitiated thermal imaging, thermal transfer) or inkjet printing.

[0366] Furthermore, the electronic devices of the present invention are preferably manufactured by applying one or more layers from a solution and by applying one or more layers by a sublimation method.

[0367] According to the present invention, the electronic device can be used in displays, as a light source in lighting applications, and as a light source in medical and / or beauty applications. Example

[0368] 1) Methods for determining HOMO energy

[0369] The HOMO energy was determined through quantum chemical calculations. For this purpose, the software package "Gaussian16(Rev. B.01)" (Gaussian Inc.) was used. The neutral singlet ground state was optimized at the B3LYP / 6-31G(d) level. For the B3LYP / 6-31G(d) optimized ground state energy, the HOMO and LUMO values ​​were determined at the B3LYP / 6-31G(d) level. Then, TD-DFT singlet and triplet excitations (vertical excitations) were calculated using the same method (B3LYP / 6-31G(d)) and optimized ground state geometry. Standard settings for SCF and gradient convergence were used.

[0370] Energy calculations yield the HOMO as the last orbital occupied by two electrons (α occ. eigenvalue) (in Hartley units), where HEh represents the HOMO energy (in Hartley units). This is used to determine the HOMO value in electron volts, calibrated by cyclic voltammetry measurements, as follows:

[0371] HOMO(eV) = (HEh*27.212)*0.8308-1.118

[0372] In the context of this application, this value is considered to be the HOMO of the material.

[0373] For the compounds used, the following data were obtained:

[0374]

[0375] The HOMO value of the compound used in this application is therefore higher than that of HTM-Ref.

[0376] 2) Methods for determining hole mobility

[0377] A glass plate coated with 50 nm thick structured ITO (indium tin oxide) was treated with oxygen plasma before coating, followed by argon plasma treatment. These plasma-treated glass plates formed a substrate, on which a 20 nm thick layer of the material to be analyzed, p-type doped with F4TCNQ (F4TCNQ concentration = 5 volume%), was applied. A 100 nm thick layer of the material to be analyzed was then applied via vapor deposition, followed by a 100 nm thick aluminum layer. The hole-only device (HOD) was then encapsulated. The current-voltage characteristics of the HOD were measured. The mobility could then be determined by fitting the Mott-Gurney equation for space charge confinement current to the current-voltage characteristics. In the following equation, µ0 is the hole mobility.

[0378]

[0379] J – Current density

[0380] V – Voltage, minus the built-in voltage

[0381] L – Thickness of the undoped HTM layer

[0382] vacuum dielectric constant

[0383] ε – Relative permittivity of the material being analyzed

[0384] Hole mobility

[0385]

[0386] 3) Production and analysis of OLED components

[0387] A) General experimental setup and testing methods

[0388] A glass substrate coated with a 50 nm thick structured ITO (indium tin oxide) was treated with oxygen plasma before coating, followed by argon plasma treatment. These plasma-treated glass substrates formed the substrate for applying OLEDs.

[0389] The OLED has the following layer structure: substrate / hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / emitting layer (EML) / optional hole blocking layer (HBL) / electron transport layer (ETL), and finally a cathode. The cathode is formed of an aluminum layer with a thickness of 100 nm. The exact structure of the OLED can be seen in the table shown below. The materials required to produce the OLED are shown in Table 5.

[0390] All materials are applied in a vacuum chamber via thermal vapor deposition. In this case, the luminescent layer always consists of a matrix material and a luminescent material, which is co-evaporated into the matrix material in a specific volume ratio (doped). A figure given, for example, in the form of SMB:SEB (95%:5%), indicates that material SMB is present in the layer at a volume ratio of 95%, while material SEB is present in the layer at a volume ratio of 5%. The case for the electron transport layer is similar.

[0391] The OLED was characterized in a standard manner. For this purpose, the electroluminescence spectrum, current efficiency (measured in cd / A), and lifetime were determined. The electroluminescence spectrum was at 1000 cd / m². 2 The luminous density was measured at 1000 cd / m², and the CIE 1931 x and y color coordinates were calculated accordingly. All analyzed OLEDs were measured at 1000 cd / m². 2 Both have CIE x / y values ​​of 0.14 / 0.14. SE1000 indicates a value of 1000 cd / m. 2 The achieved current efficiency. Lifetime LD is defined as the current efficiency achieved at 60 mA / cm². 2 The time after the luminous density drops from the initial luminous density to 95% during constant current operation.

[0392] B) In the first experiment, an OLED containing HTM-Ref in HTL (OLED V1) will be compared with an OLED having compound HTM-1 in HIL and HTL instead of HTM-Ref and having the same structure in other respects (OLED V2) or an OLED having compound HTM-3, HTM-4 or HTM-5 in HIL and HTL instead of HTM-Ref and having the same structure in other respects (OLED E2, E3 or E4).

[0393]

[0394] For OLED E1, a significant lifetime improvement was achieved compared to OLED V1 (LD = 30 h) (LD = 60 h). For OLED E2, a lifetime improvement was achieved with the same efficiency compared to OLED V1 (LD = 50 h). For OLED E3, a lifetime improvement was achieved with the same efficiency compared to OLED V1 (LD = 40 h). For OLED E4, a lifetime improvement was achieved with the same efficiency compared to OLED V1 (LD = 45 h).

[0395] C) In the second experiment, the above-mentioned OLED E1 was compared with OLED E5. The only difference between OLED E5 and OLED E1 is that it contains compound ETM-2 in ETL instead of compound ETM-1.

[0396]

[0397] For OLED E5, compared to OLED E1 (SE1000 = 10.1), efficiency is improved (SE1000 = 10.5). Compared to E1, the lifetime of E5 is slightly reduced.

[0398] For the other three HTM materials, HTM-3 to HTM-5, comparable results can be obtained in this laminated structure, especially improvements in efficiency.

[0399] D) In ​​the third experiment, the above OLED E5 was compared with OLED E6. The only difference between OLED E6 and OLED E5 is that OLED E6 contains compound EBM-2 in EBL instead of compound EBM-1.

[0400]

[0401] This achieves double the lifetime of E6 (LD = 80 h) compared to E5 (LD = 40 h). The efficiency is constant to slightly higher, so this OLED significantly outperforms other OLEDs in terms of the combination of lifetime and efficiency.

[0402] For the other three HTM materials, HTM-3 to HTM-5, comparable results can be obtained in this laminated structure, especially improvements in efficiency.

[0403] E) In another experiment, an OLED containing compound HBM-1 in HBL was demonstrated. Here, HTM contains material HTM-3, EBM contains material EBM-2, and ETL contains material ETM-3.

[0404]

[0405] In this experiment, the best lifetime (LD = 95 h) was obtained for all tested OLEDs, with the efficiency of SE1000 being similar to that of the other tested OLEDs. This demonstrates that improvements can be achieved by combining compound HBM-1 in HBL with compounds from HIL, HTL, EBL, and ETL.

[0406]

[0407]

Claims

1. An electronic device, the electronic device comprising an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, characterized in that... - There are one or more layers containing a compound of formula (H) between the anode and the light-emitting layer. Formula (H) in: Ar H1 In each case, they may be the same or different and are selected from those having 6 to 40 aromatic ring atoms and are R H1 Aromatic ring systems with substituted groups, and aromatic ring systems having 5 to 40 aromatic ring atoms and being R H1 Heteroaromatic ring systems with substituted groups; R H1 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. H2 CN, Si(R) H2 )3, N(R H2 )2, P(=O)(R H2 )2, OR H2 S(=O)R H2 S(=O)2R H2 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R H1 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R H2 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R H2 C=CR H2 -、-C≡C-、Si(R H2 2. C=O, C=NR H2 -C(=O)O-, -C(=O)NR H2 -、NR H2 P(=O)(R) H2 Replace with -O-, -S-, SO or SO2; R H2 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. H3 CN, Si(R) H3 )3, N(R H3 )2, P(=O)(R H3 )2, OR H3 S(=O)R H3 S(=O)2R H3 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R H2 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R H3 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R H3 C=CR H3 -、-C≡C-、Si(R H3 2. C=O, C=NR H3 -C(=O)O-, -C(=O)NR H3 -、NR H3 P(=O)(R) H3 Replace with -O-, -S-, SO or SO2; R H3 In each case, the same or different and selected from H, D, F, Cl, Br, I, CN, alkyl or alkoxy groups having 1 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; wherein two or more R H3 The groups can be linked together and can form rings; and said alkyl, alkoxy, alkenyl, and alkynyl groups, aromatic ring systems, and heteroaromatic ring systems can be substituted by one or more groups selected from F and CN; and The compound of formula (H) has a HOMO of not less than -4.72 eV; and - Between the light-emitting layer and the cathode, there exists one or more layers containing compounds selected from the following formulas (E 1) to (E 603).

2. An electronic device, the electronic device comprising an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, characterized in that... -A layer containing one or more compounds of formula (H-1) or (H-2) exists between the anode and the light-emitting layer. Equation (H-1) Equation (H-2) The spirodifluorene group, fluorene group, and optionally present benzene group can be R at each unoccupied position. H1 Group substitution, and in addition: Ar H1 In each case, they may be the same or different and are selected from those having 6 to 40 aromatic ring atoms and are R H1 Aromatic ring systems with substituted groups, and aromatic ring systems having 5 to 40 aromatic ring atoms and being R H1 Heteroaromatic ring systems with substituted groups; R H1 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. H2 CN, Si(R) H2 )3, N(R H2 )2, P(=O)(R H2 )2, OR H2 S(=O)R H2 S(=O)2R H2 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R H1 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R H2 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R H2 C=CR H2 -、-C≡C-、Si(R H2 2. C=O, C=NR H2 -C(=O)O-, -C(=O)NR H2 -、NR H2 P(=O)(R) H2 Replace with -O-, -S-, SO or SO2; R H2 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. H3 CN, Si(R) H3 )3, N(R H3 )2, P(=O)(R H3 )2, OR H3 S(=O)R H3 S(=O)2R H3 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R H2 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R H3 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R H3 C=CR H3 -、-C≡C-、Si(R H3 2. C=O, C=NR H3 -C(=O)O-, -C(=O)NR H3 -、NR H3 P(=O)(R) H3 Replace with -O-, -S-, SO or SO2; R H3 In each case, the same or different and selected from H, D, F, Cl, Br, I, CN, alkyl or alkoxy groups having 1 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; wherein two or more R H3 The groups can be linked together and can form rings; and said alkyl, alkoxy, alkenyl, and alkynyl groups, aromatic ring systems, and heteroaromatic ring systems can be substituted by one or more groups selected from F and CN; and m can be 0, 1, 2, or 3; There exists at least one R H1 It is bonded to the spirodifluorenyl group or the aromatic ring of the fluorenyl group, and is selected from those having 1 to 20 carbon atoms and being R H2 A straight-chain alkyl group substituted with a radical, having 3 to 20 carbon atoms and being R H2 Branched or cyclic alkyl groups substituted with radicals, and aromatic rings having 6 to 40 atoms and being R-substituted. H2 Aromatic ring systems with substituted groups; and - Between the light-emitting layer and the cathode, there exists one or more layers containing compounds selected from the following formulas (E 1) to (E 603).

3. An electronic device, the electronic device comprising an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, characterized in that... - There is one or more layers containing compounds selected from (1) to (527) between the anode and the light-emitting layer. and - There are one or more layers containing a compound of formula (E) between the light-emitting layer and the cathode. Equation (E) in: A is or The dashed lines indicate the bonds that connect to the rest of the compound of formula (E); Z in When the group is bonded to it, it is C and when there is no The groups bonded to them are the same or different in each case and are selected from CR. 2 and N; X is the same or different in each case and is selected from N and CR. 4 Where at least one X is N; Ar 1 In each case, they may be the same or different and are selected from those having 6 to 40 aromatic ring atoms and are R 3 Aromatic ring systems with substituted groups, and aromatic ring systems having 5 to 40 aromatic ring atoms and being R 3 Heteroaromatic ring systems with substituted groups; Ar 2 In each case, they may be the same or different and are selected from those having 6 to 40 aromatic ring atoms and are R 5 Aromatic ring systems with substituted groups, and aromatic ring systems having 5 to 40 aromatic ring atoms and being R 5 Heteroaromatic ring systems with substituted groups; R 1 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. 6 CN, Si(R) 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 S(=O)R 6 S(=O)2R 6 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R 1 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R 6 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R 6 C=CR 6 -、-C≡C-、Si(R 6 2. C=O, C=NR 6 -C(=O)O-, -C(=O)NR 6 -、NR 6 P(=O)(R) 6 Replace with -O-, -S-, SO or SO2; R 2 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. 6 CN, Si(R) 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 S(=O)R 6 S(=O)2R 6 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R 2 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R 6 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R 6 C=CR 6 -、-C≡C-、Si(R 6 2. C=O, C=NR 6 -C(=O)O-, -C(=O)NR 6 -、NR 6 P(=O)(R) 6 Replace with -O-, -S-, SO or SO2; R 3 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. 6 CN, Si(R) 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 S(=O)R 6 S(=O)2R 6 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R 3 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R 6 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R 6 C=CR 6 -、-C≡C-、Si(R 6 2. C=O, C=NR 6 -C(=O)O-, -C(=O)NR 6 -、NR 6 P(=O)(R) 6 Replace with -O-, -S-, SO or SO2; R 4 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. 6 CN, Si(R) 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 S(=O)R 6 S(=O)2R 6 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R 4 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R 6 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R 6 C=CR 6 -、-C≡C-、Si(R 6 2. C=O, C=NR 6 -C(=O)O-, -C(=O)NR 6 -、NR 6 P(=O)(R) 6 Replace with -O-, -S-, SO or SO2; R 5 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. 6 CN, Si(R) 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 S(=O)R 6 S(=O)2R 6 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R 5 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R 6 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R 6 C=CR 6 -、-C≡C-、Si(R 6 2. C=O, C=NR 6 -C(=O)O-, -C(=O)NR 6 -、NR 6 P(=O)(R) 6 Replace with -O-, -S-, SO or SO2; R 6 In each case, they may be the same or different and are selected from H, D, F, Cl, Br, I, C(=O)R. 7 CN, Si(R) 7 )3, N(R 7 )2, P(=O)(R 7 )2, OR 7 S(=O)R 7 S(=O)2R 7 A straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms; a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms; an alkenyl or alkynyl group having 2 to 20 carbon atoms; an aromatic ring system having 6 to 40 aromatic ring atoms; and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; wherein two or more R 6 Groups can be linked together and can form rings; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups, as well as the aromatic and heteroaromatic ring systems, are each R 7 Group substitution; and one or more CH2 groups among said alkyl, alkoxy, alkenyl, and alkynyl groups can be -R 7 C=CR 7 -、-C≡C-、Si(R 7 2. C=O, C=NR 7 -C(=O)O-, -C(=O)NR 7 -、NR 7 P(=O)(R) 7 Replace with -O-, -S-, SO or SO2; R 7 In each case, the same or different and selected from H, D, F, Cl, Br, I, CN, alkyl or alkoxy groups having 1 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; wherein two or more R 7 The groups can be linked together and can form rings; and the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems can be substituted by one or more groups selected from F and CN; n can be 0, 1, 2, 3, or 4.

4. An electronic device, the electronic device comprising an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, characterized in that... - There is one or more layers containing compounds selected from (1) to (527) between the anode and the light-emitting layer. and - Between the light-emitting layer and the cathode, there exists one or more layers containing compounds selected from the following formulas (E 1) to (E 603).

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