Electronic device

Abstract

To provide a long-life and highly efficient electronic device.SOLUTION: An electronic device includes a compound of formula (H) in a layer between the anode and the light-emitting layer, and further comprising a compound of formula (E) in a layer between the light-emitting layer and the cathode.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present application relates to an electronic device that contains a specific amine compound in a hole-transporting layer and a compound of a specific structural type in an electron-transporting layer.

[0002] In the context of this application, electronic devices are understood to mean so-called organic electronic devices that contain organic semiconductor materials as functional materials. More specifically, they are understood to mean OLEDs (organic electroluminescent devices). The term OLED is understood to mean an electronic device that has one or more layers containing organic compounds and emits light when a voltage is applied. The general principles of the structure and function of OLEDs are known to those skilled in the art.

[0003] There continues to be strong interest in improving performance data for electronic devices, especially OLEDs.

[0004] Known materials for hole-transporting layers in electronic devices are a large number of different materials, most of which form part of the substance class of triarylamines, such as N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (NPD) or tris(4-carbazolyl-9-ylphenyl)amine (TCTA). In addition, spirobifluorenyl monoamines and fluorenyl monoamines have recently become known as materials for hole-transporting layers.

[0005] Similarly, there are many different compounds known for electron transport in electronic devices. Often, compounds with electron-deficient nitrogen-containing heteroaromatic six-membered rings, especially triazine derivatives, are used for this purpose.

[0006] In the context of the present invention, it has now been discovered that certain spirobifluorenylamines or combinations of fluorenylamines, in particular in hole-transporting layers, which comprise an electron-deficient nitrogen-containing six-membered heteroaromatic ring in the electron-transporting layer, lead to particularly good properties of electronic devices, in particular long lifetimes, high efficiencies and low operating voltages.

[0007] Therefore, the present application is -Formula (H)

[0008] [ka]

[0009] (In the formula, Ar H1 are the same or different in each occurrence and have 6 to 40 aromatic ring atoms; R H1 Aromatic ring systems substituted by radicals and having 5 to 40 aromatic ring atoms, R H1 a heteroaromatic ring system substituted by a radical; R H1 are the same or different in each case and are 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 linear 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; two or more R H1 The radicals may be linked to each other or may form a ring; the mentioned alkyl, alkoxy, alkenyl and alkynyl groups, and the mentioned aromatic and heteroaromatic ring systems, are each R H2one or more CH groups in the mentioned alkyl, alkoxy, alkenyl and alkynyl groups may be substituted by -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 ), -O-, -S-, SO or SO2; R H2 are the same or different in each case and are 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 linear 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; two or more R H2 The radicals may be linked to each other or may form a ring; the mentioned alkyl, alkoxy, alkenyl and alkynyl groups, and the mentioned aromatic and heteroaromatic ring systems, are each R H3 one or more CH groups in the mentioned alkyl, alkoxy, alkenyl and alkynyl groups may be substituted by -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 ), -O-, -S-, SO or SO2; R H3are the same or different in each occurrence and are 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; H3 The radicals may be linked to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic and heteroaromatic ring systems mentioned may be substituted by one or more radicals selected from F and CN. is present between the anode and the light-emitting layer; the compound of formula (H) has a HOMO of not lower than −4.72 eV, more preferably not lower than −4.71 eV, the HOMO being determined by the method described in Examples, Section 1; -Formula (E)

[0010] [ka]

[0011] (In the formula, A is,

[0012] [ka]

[0013] where the dotted line indicates the connection to the rest of the equation; Z is

[0014] [ka]

[0015] C, in each case the same or different, when groups are attached thereto;

[0016] [ka]

[0017] If no groups are attached to it, CR 2 and N; X is the same or different in each occurrence, and N and CR 4 wherein at least one X is N; Ar 1 are the same or different in each occurrence and have 6 to 40 aromatic ring atoms; R 3 Aromatic ring systems substituted by radicals and having 5 to 40 aromatic ring atoms, R 3 a heteroaromatic ring system substituted by a radical; Ar 2 are the same or different in each occurrence and have 6 to 40 aromatic ring atoms; R 5 Aromatic ring systems substituted by radicals and having 5 to 40 aromatic ring atoms, R 5 a heteroaromatic ring system substituted by a radical; R 1 are the same or different in each case and are 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 linear 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; two or more R 1 The radicals may be linked to each other or may form a ring; the mentioned alkyl, alkoxy, alkenyl and alkynyl groups, and the mentioned aromatic and heteroaromatic ring systems, are each R6 one or more CH groups in the mentioned alkyl, alkoxy, alkenyl and alkynyl groups may be substituted by -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 ), -O-, -S-, SO or SO2; R 2 are the same or different in each case and are 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 linear 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; two or more R 2 The radicals may be linked to each other or may form a ring; the mentioned alkyl, alkoxy, alkenyl and alkynyl groups, and the mentioned aromatic and heteroaromatic ring systems, are each R 6 one or more CH groups in the mentioned alkyl, alkoxy, alkenyl and alkynyl groups may be substituted by -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 ), -O-, -S-, SO or SO2; R 3are the same or different in each case and are 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 linear 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; two or more R 3 The radicals may be linked to each other or may form a ring; the mentioned alkyl, alkoxy, alkenyl and alkynyl groups, and the mentioned aromatic and heteroaromatic ring systems, are each R 6 one or more CH groups in the mentioned alkyl, alkoxy, alkenyl and alkynyl groups may be substituted by -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 ), -O-, -S-, SO or SO2; R 4 are the same or different in each case and are 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 linear 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; two or more R 4 The radicals may be linked to each other or may form a ring; the mentioned alkyl, alkoxy, alkenyl and alkynyl groups, and the mentioned aromatic and heteroaromatic ring systems, are each R 6 one or more CH groups in the mentioned alkyl, alkoxy, alkenyl and alkynyl groups may be substituted by -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 ), -O-, -S-, SO or SO2; R 5 are the same or different in each case and are 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 linear 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; two or more R 5 The radicals may be linked to each other or may form a ring; the mentioned alkyl, alkoxy, alkenyl and alkynyl groups, and the mentioned aromatic and heteroaromatic ring systems, are each R 6one or more CH groups in the mentioned alkyl, alkoxy, alkenyl and alkynyl groups may be substituted by -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 ), -O-, -S-, SO or SO2; R 6 are the same or different in each case and are 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 linear 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; two or more R 6 The radicals may be linked to each other or may form a ring; the mentioned alkyl, alkoxy, alkenyl and alkynyl groups, and the mentioned aromatic and heteroaromatic ring systems, are each R 7 one or more CH groups in the mentioned alkyl, alkoxy, alkenyl and alkynyl groups may be substituted by -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 ), -O-, -S-, SO or SO2; R 7are the same or different in each occurrence and are 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; 7 The radicals may be bonded to one another or may form rings; the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic and heteroaromatic ring systems mentioned may be substituted by one or more radicals selected from F and CN; n is 0, 1, 2, 3, or 4) between the light-emitting layer and the cathode, one or more layers containing a compound of The present invention provides an electronic device comprising an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, characterized in that

[0018] When n=0, Ar 1 group is absent, and Ar 1 The two groups bonded to the group are directly bonded to each other. When n=2, 3, or 4, two, three, or four consecutively bonded Ar 1 There is a group.

[0019] By "larger" or "higher" HOMO in the context of this application, it is understood to mean that the value is less negative; for example, a HOMO of -5.2 eV is larger / higher than a HOMO of -5.3 eV.

[0020] The following definitions are applicable to chemical groups used in this application unless any further specific definition is given.

[0021] An aryl group in the context of the present invention is understood to mean either a single aromatic ring, i.e., benzene, or a fused aromatic polycycle, such as naphthalene, phenanthrene, or anthracene. A fused aromatic polycycle in the context of the present application consists of two or more single aromatic rings fused to each other. Fusion between rings is understood here to mean that the rings share at least one edge with each other. An aryl group in the context of the present invention contains 6 to 40 aromatic ring atoms. In addition, an aryl group does not contain any heteroatoms as aromatic ring atoms, but only carbon atoms.

[0022] A heteroaryl group in the context of the present invention is understood to mean either a single heteroaromatic ring, such as pyridine, pyrimidine, or thiophene, or a fused heteroaromatic polycycle, such as quinoline or carbazole. A fused heteroaromatic polycycle in the context of the present application consists of two or more single aromatic or heteroaromatic rings fused together, at least one of the aromatic and heteroaromatic rings being a heteroaromatic ring. Fusion between rings is understood here to mean that the rings share at least one edge with each other. A heteroaryl group in the context of the present invention contains 5 to 40 aromatic ring atoms, at least one of which is a heteroatom. The heteroatom in the heteroaryl group is preferably selected from N, O, and S.

[0023] The aryl or heteroaryl groups, each of which may be substituted by the above-mentioned radicals, are especially benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, triphenylene, fluoranthene, benzanthracene, benzophenanthrene, tetracene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indophenyl, benzophenone, benzoisobenzothiophene, dibenzothiophene, pyrrole, indophenyl, benzophenone, benzoisobenzothiophene, dibenzothiophene, pyrrole, indophenyl, benzophenone, benzoisobenzothiophene, dibenzoisobenzothiophene, pyrrole, indophenyl, benzoisobenzothiophene, benzoisobenzothiophene, dibenzoisobenzothiophene, pyrrole, indophenyl, benzoisobenzothiophene, benzoisobenzothiophene, dibenzoisobenzothiophene, pyrrole, indophenyl, benzoisobenzothiophene, benzoisobenzothiophene, dibenzoisobenzothiophene, pyrrole, indophenyl, benzoisobenzothiophene, benzoisobenzofuran, dibenzoisobenzothiophene, pyrrole, indophenyl ...furan, pyrrole, indophenyl, benzoisobenzofuran, dibenzoiso benzoindole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, benzimidazolo[1,2-a]benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazineimidazole, quinoxalineimidazole, oxazole, benzimidazole benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, pyrazine, phenazine, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole is understood to mean groups derived from 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine and benzothiadiazole.

[0024] An aromatic ring system in the context of this invention does not necessarily contain only aryl groups, but may also contain one or more additional non-aromatic rings fused to at least one aryl group. These non-aromatic rings contain only carbon atoms as ring atoms. Examples of groups encompassed by this definition are tetrahydronaphthalene, fluorene, and spirobifluorene. Additionally, the term "aromatic ring system" includes systems consisting of two or more aromatic ring systems bonded to each other via a single bond, such as biphenyl, terphenyl, 7-phenyl-2-fluorenyl, quaterphenyl, and 3,5-diphenyl-1-phenyl. An aromatic ring system in the context of this invention contains 6 to 40 carbon atoms in the ring system but does not contain heteroatoms. The definition of "aromatic ring system" does not include heteroaryl groups.

[0025] A heteroaromatic ring system conforms to the definition of an aromatic ring system above, except that it must contain at least one heteroatom as a ring atom. As with aromatic ring systems, a heteroaromatic ring system need not contain only aryl and heteroaryl groups, but may also contain one or more additional non-aromatic rings fused to at least one aryl or heteroaryl group. A non-aromatic ring may contain only carbon atoms as ring atoms, or it may contain one or more additional heteroatoms, preferably selected from N, O, and S. An example of such a heteroaromatic ring system is benzopyranyl. Additionally, the term "heteroaromatic ring system" is understood to mean a system consisting of two or more aromatic or heteroaromatic ring systems bonded to each other via a single bond, such as 4,6-diphenyl-2-triazinyl. A heteroaromatic ring system in the context of the present invention contains 5 to 40 ring atoms selected from carbon and heteroatoms, with at least one of the ring atoms being a heteroatom. The heteroatoms in a heteroaromatic ring system are preferably selected from N, O, and S.

[0026] Thus, the terms "heteroaromatic ring system" and "aromatic ring system," as defined herein, 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, which may be present as a ring atom of either a non-aromatic or aromatic heterocyclic ring.

[0027] According to the above definitions, any aryl group is encompassed by the term "aromatic ring system" and any heteroaryl group is encompassed by the term "heteroaromatic ring system".

[0028] An aromatic ring system having 6 to 40 aromatic ring atoms or a heteroaromatic ring system having 5 to 40 aromatic ring atoms is understood to mean, in particular, a radical derived from the radicals mentioned above under the aryl radical and heteroaryl radical, and from biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, indenofluorene, truxene, isotruxene, spirotruxene, spiroisotruxene, indenocarbazole, or a combination of these radicals.

[0029] In the context of the present invention, linear 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 are understood to mean groups in which the individual hydrogen atoms or CH groups may also be substituted by the groups mentioned above in the definition of the radicals, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, neopentyl, ... cyclohexyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl or octynyl radical.

[0030] In the alkoxy or thioalkyl groups having 1 to 20 carbon atoms, individual hydrogen atoms or CH groups may also be replaced by the groups mentioned above in the definition of the radicals, preferably methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy, 2,2,2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i -butylthio, s-butylthio, t-butylthio, n-pentylthio, s-pentylthio, n-hexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, cyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthio, cyclooctenylthio, ethynylthio, propynylthio, butynylthio, pentynylthio, hexynylthio, heptynylthio or octynylthio.

[0031] The expression that two or more radicals may join together to form a ring is to be understood in the context of this application to mean, inter alia, that the two radicals are bonded to one another by a chemical bond, but in addition, the expression should also be understood to mean that if one of the two radicals is hydrogen, the second radical is bonded to the position where the hydrogen atom was bonded, thereby forming a ring.

[0032] The compounds of formula (H) preferably have a HOMO not lower than −4.72 eV and not higher than −4.55 eV, measured, for example, as specified in section 1.

[0033] In addition, the compound of formula (H) is preferably 2*10 -4 ~8*10 -4 cm 2 / Vs, preferably 3*10 -4 cm 2 / Vs~6*10 -4 cm 2 / Vs. The hole mobility is measured, for example, as specified in section 2).

[0034] Preferably, the above preferred values ​​for hole mobility and for the HOMO are present in combination in compounds of formula (H).

[0035] In the compound of formula (H), preferably at least one Ar H1 The group more preferably has at least two Ar H1 The group has 6 to 40 aromatic ring atoms, and R H1 The ring system is selected from aromatic ring systems substituted by radicals.

[0036] Preferably, Ar H1 are the same or different in each occurrence and are selected from phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, fluorenyl, especially 9,9′-dimethylfluorenyl and 9,9′-diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzofuranyl, benzothiophenyl, benzo-fused dibenzofuranyl, benzo-fused dibenzothiophenyl, naphthyl-substituted phenyl, fluorenyl-substituted phenyl, spirobifluorenyl-substituted phenyl, dibenzofuranyl-substituted phenyl, dibenzothiophenyl-substituted phenyl, carbazolyl-substituted phenyl, pyridyl-substituted phenyl, pyrimidyl-substituted phenyl, and triazinyl-substituted phenyl, each of which is selected from R H1 It is substituted by a radical.

[0037] Preferably, R H1At least one Ar containing and substituted by a radical H1 The group contains 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, each of which is R H1 is substituted by a radical, more preferably R H1 2-spirobifluorenyl and 2-fluorenyl are preferred, each of which is selected from spirobifluorenyl substituted by the radical R H1 It is substituted by a radical.

[0038] Preferably, at least one R H1 , especially Ar H1 and R H2 A linear alkyl group substituted with a radical, having 3 to 20 carbon atoms, R H2 a branched or cyclic alkyl group substituted with a radical, and 6 to 40 aromatic ring atoms, R H2 R selected from aromatic ring systems substituted by radicals H1 is present in the compound of formula (H). More preferably, it has 1 to 20 carbon atoms and R H2 A linear alkyl group substituted with a radical, having 3 to 20 carbon atoms, R H2 a branched or cyclic alkyl group substituted with a radical, and 6 to 40 aromatic ring atoms, R H2 one, two, three or four identical R selected from aromatic ring systems substituted by radicals H1 groups or different R H1 groups are present in the compound of formula (H), and the remaining R H1 The group is H.

[0039] R H1 are preferably in each case the same or different and are H, D, F, CN, Si(RH2 )3, N(R H2 )2, selected from linear alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy 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; the mentioned alkyl and alkoxy groups, the mentioned aromatic ring systems and the mentioned heteroaromatic ring systems are each selected from R H2 one or more CH groups in the mentioned alkyl or alkoxy groups may be substituted by -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 More preferably, R H1 are the same or different in each occurrence and are selected from H, D, F, CN, a linear 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, and said alkyl group, said aromatic ring system, and said heteroaromatic ring system are each selected from R H2 Most preferably, R H1 are in each occurrence the same or different and are selected from linear 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, and the mentioned alkyl groups and the mentioned aromatic ring systems are each R H2 It is substituted by a radical.

[0040] R H2are preferably in each occurrence the same or different and selected from H, D, F, CN, a linear 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 said alkyl group, said aromatic ring system and said heteroaromatic ring system are each selected from R H3 More preferably, R H2 are in each occurrence the same or different and are selected from H, a linear 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, and the mentioned alkyl group and the mentioned aromatic ring system are each R H3 It is substituted by a radical.

[0041] R H3 are preferably the same or different in each occurrence and are 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.

[0042] A preferred embodiment of the compound of formula (H) is the compound of formula (H-1) or (H-2):

[0043] [ka]

[0044] (wherein, when the subscript m=0, 1, 2 or 3, the occurring radicals are as defined above, preferably corresponding to the preferred embodiments specified above, and the spirobifluorenyl radical, the fluorenyl radical and the optionally present phenyl radical in the formula are each R H1 Among the two formulas, formula (H-1) is particularly preferred. Preferably, Ar in the above formula H1The groups are in each case the same or different and are selected from phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, fluorenyl, especially 9,9′-dimethylfluorenyl and 9,9′-diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzofuranyl, benzothiophenyl, benzo-fused dibenzofuranyl, benzo-fused dibenzothiophenyl, naphthyl-substituted phenyl, fluorenyl-substituted phenyl, spirobifluorenyl-substituted phenyl, dibenzofuranyl-substituted phenyl, dibenzothiophenyl-substituted phenyl, carbazolyl-substituted phenyl, pyridyl-substituted phenyl, pyrimidyl-substituted phenyl, and triazinyl-substituted phenyl, each of which may be selected from R H1 The suffix m is 0 or 1. For clarity, the suffix m=0 means that the amino group and the spirobifluorenyl or fluorenyl group are directly bonded to each other. The suffix m=2 or 3 means that two or three phenyl groups are directly arranged in succession.

[0045] Preferably, in formulas (H-1) and (H-2), the spirobifluorenyl group or the fluorenyl group is bonded to an aromatic ring and has 1 to 20 carbon atoms, and R H2 A linear alkyl group substituted with a radical, having 3 to 20 carbon atoms, R H2 a branched or cyclic alkyl group substituted with a radical, and 6 to 40 aromatic ring atoms, R H2 At least one R selected from an aromatic ring system substituted by a radical H1 exists.

[0046] Therefore, the present application further provides: Formula (H-1) or (H-2)

[0047] [ka]

[0048] wherein the spirobifluorenyl group, the fluorenyl group, and the optionally present phenylene group are each R H1 and optionally substituted by radicals: Ar H1 are the same or different in each occurrence and have 6 to 40 aromatic ring atoms; R H1 Aromatic ring systems substituted by radicals and having 5 to 40 aromatic ring atoms, R H1 a heteroaromatic ring system substituted by a radical; R H1 are the same or different in each case and are 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 linear 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; two or more R H1 The radicals may be linked to each other or may form a ring; the mentioned alkyl, alkoxy, alkenyl and alkynyl groups, and the mentioned aromatic and heteroaromatic ring systems, are each R H2 one or more CH groups in the mentioned alkyl, alkoxy, alkenyl and alkynyl groups may be substituted by -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), -O-, -S-, SO or SO2; R H2 are the same or different in each case and are 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 linear 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; two or more R H2 The radicals may be linked to each other or may form a ring; the mentioned alkyl, alkoxy, alkenyl and alkynyl groups, and the mentioned aromatic and heteroaromatic ring systems, are each R H3 one or more CH groups in the mentioned alkyl, alkoxy, alkenyl and alkynyl groups may be substituted by -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 ), -O-, -S-, SO or SO2; R H3 are the same or different in each occurrence and are 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; H3The radicals may be bonded to one another or may form rings; the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic and heteroaromatic ring systems mentioned may be substituted by one or more radicals selected from F and CN; m is 0, 1, 2 or 3; spirobifluorenyl or fluorenyl group, and has 1 to 20 carbon atoms attached to the aromatic ring, R H2 A linear alkyl group substituted with a radical, having 3 to 20 carbon atoms, R H2 a branched or cyclic alkyl group substituted with a radical, and 6 to 40 aromatic ring atoms, R H2 At least one R selected from an aromatic ring system substituted by a radical H1 exists) is present between the anode and the light-emitting layer, and -Formula (E)

[0049] [ka]

[0050] (In the formula, A is,

[0051] [ka]

[0052] where the dotted line indicates the connection to the rest of the equation; Z is

[0053] [ka]

[0054] C, in each case the same or different, when groups are attached thereto;

[0055] [ka]

[0056] If no groups are attached to it, CR 2 and N; X is the same or different in each occurrence, and N and CR 4 wherein at least one X is N; Ar 1 are the same or different in each occurrence and have 6 to 40 aromatic ring atoms; R 3 Aromatic ring systems substituted by radicals and having 5 to 40 aromatic ring atoms, R 3 a heteroaromatic ring system substituted by a radical; Ar 2 are the same or different in each occurrence and have 6 to 40 aromatic ring atoms; R 5 Aromatic ring systems substituted by radicals and having 5 to 40 aromatic ring atoms, R 5 a heteroaromatic ring system substituted by a radical; R 1 are the same or different in each case and are 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 linear 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; two or more R 1 The radicals may be linked to each other or may form a ring; the mentioned alkyl, alkoxy, alkenyl and alkynyl groups, and the mentioned aromatic and heteroaromatic ring systems, are each R6 one or more CH groups in the mentioned alkyl, alkoxy, alkenyl and alkynyl groups may be substituted by -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 ), -O-, -S-, SO or SO2; R 2 are the same or different in each case and are 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 linear 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; two or more R 2 The radicals may be linked to each other or may form a ring; the mentioned alkyl, alkoxy, alkenyl and alkynyl groups, and the mentioned aromatic and heteroaromatic ring systems, are each R 6 one or more CH groups in the mentioned alkyl, alkoxy, alkenyl and alkynyl groups may be substituted by -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 ), -O-, -S-, SO or SO2; R 3are the same or different in each case and are 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 linear 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; two or more R 3 The radicals may be linked to each other or may form a ring; the mentioned alkyl, alkoxy, alkenyl and alkynyl groups, and the mentioned aromatic and heteroaromatic ring systems, are each R 6 one or more CH groups in the mentioned alkyl, alkoxy, alkenyl and alkynyl groups may be substituted by -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 ), -O-, -S-, SO or SO2; R 4 are the same or different in each case and are 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 linear 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; two or more R 4 The radicals may be linked to each other or may form a ring; the mentioned alkyl, alkoxy, alkenyl and alkynyl groups, and the mentioned aromatic and heteroaromatic ring systems, are each R 6 one or more CH groups in the mentioned alkyl, alkoxy, alkenyl and alkynyl groups may be substituted by -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 ), -O-, -S-, SO or SO2; R 5 are the same or different in each case and are 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 linear 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; two or more R 5 The radicals may be linked to each other or may form a ring; the mentioned alkyl, alkoxy, alkenyl and alkynyl groups, and the mentioned aromatic and heteroaromatic ring systems, are each R 6one or more CH groups in the mentioned alkyl, alkoxy, alkenyl and alkynyl groups may be substituted by -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 ), -O-, -S-, SO or SO2; R 6 are the same or different in each case and are 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 linear 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; two or more R 6 The radicals may be linked to each other or may form a ring; the mentioned alkyl, alkoxy, alkenyl and alkynyl groups, and the mentioned aromatic and heteroaromatic ring systems, are each R 7 one or more CH groups in the mentioned alkyl, alkoxy, alkenyl and alkynyl groups may be substituted by -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 ), -O-, -S-, SO or SO2; R 7are the same or different in each occurrence and are 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; 7 The radicals may be linked to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic and heteroaromatic ring systems mentioned may be substituted with one or more radicals selected from F and CN; n is 0, 1, 2, 3 or 4). between the light-emitting layer and the cathode, one or more layers containing a compound of The present invention provides an electronic device comprising an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, characterized in that

[0057] For the above embodiments, it is preferred when other preferred embodiments of compounds of formula (H), as further defined below, are present in the electronic device, rather than compounds of formula (H-1) or (H-2).

[0058] More preferably, in formulas (H-1) and (H-2), R H2 A linear alkyl group substituted with a radical, having 3 to 20 carbon atoms, R H2 a branched or cyclic alkyl group substituted with a radical, and 6 to 40 aromatic ring atoms, R H2 where one, two, three or four identical R radicals are selected from aromatic ring systems substituted by H1 groups or different R H1 groups, and the remaining R H1 The group is H.

[0059] Preferred embodiments of formula (H-1) include the following formulae (H-1-a) to (H-1-p):

[0060] [ka]

[0061] [ka]

[0062] (In the formula, R H1-1 are in each occurrence the same or different and are selected from linear 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; the mentioned alkyl groups and the mentioned aromatic ring systems are each R H2 the other variables are as defined above, preferably corresponding to the above preferred embodiments thereof, and the spirobifluorenyl and phenylene groups are substituted with R which is preferably H at each unoccupied position. H1 Among the above formulae, the formulae (H-1-a), (H-1-d), (H-1-i) and (H-1-l) are particularly preferred, in particular the formulae (H-1-d) and (H-1-l), and especially the formula (H-1-d). The phenylene group may be a para-phenylene group, a meta-phenylene group or an ortho-phenylene group.

[0063] R H1-1 It is generally preferred that R is the same or different in each occurrence and is selected from methyl, isopropyl, tert-butyl, phenyl, biphenyl, terphenyl, quaterphenyl, and naphthyl.

[0064] Preferred embodiments of formulas (H-1) and (H-2) are formulas (H-1-1) and (H-2-1)

[0065] [ka]

[0066] (wherein the occurring radicals and subscripts are as defined above and preferably correspond to the preferred embodiments thereof as specified above, and the spirobifluorenyl group, the fluorenyl group and the optionally present phenylene group in the formula are each independently selected from the group consisting of R H1 Of the two formulae, formula (H-1-1) is particularly preferred.

[0067] Particularly preferred embodiments of formula (H-1-1) are formulas (H-1-1-a) to (H-1-1-p)

[0068] [ka]

[0069] [ka]

[0070] [ka]

[0071] (In the formula, R H1-1 are in each occurrence the same or different and are selected from linear 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; the mentioned alkyl groups and the mentioned aromatic ring systems are each R H2 the other variables are as defined above, preferably corresponding to the above preferred embodiments thereof, and the spirobifluorenyl and phenylene groups are substituted with R which is preferably H at each unoccupied position. H1Among the above formulae, the formulae (H-1-1-a), (H-1-1-d), (H-1-1-i) and (H-1-1-l) are particularly preferred, in particular the formulae (H-1-1-d) and (H-1-1-l), and especially the formula (H-1-1-d). The phenylene group may be a para-phenylene group, a meta-phenylene group or an ortho-phenylene group.

[0072] Most preferably, the compound of formula (H) has the formula:

[0073] [ka]

[0074] (In the formula, R H1-1 are in each occurrence the same or different and are selected from linear 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; the mentioned alkyl groups and the mentioned aromatic ring systems are each R H2 the other variables are as defined above, preferably corresponding to the above preferred embodiments thereof, and the spirobifluorenyl group is substituted with R which is preferably H at each unoccupied position. H1 (substituted by radicals) matches one of the following:

[0075] Preferred specific embodiments of compounds of formula (H) are shown in the table below:

[0076] [ka]

[0077] [ka]

[0078] [ka]

[0079]

change

[0080]

change

[0081]

change

[0082]

change

[0083]

change

[0084]

change

[0085]

change

[0086]

change

[0087]

change

[0088]

change

[0089]

change

[0090]

change

[0091]

change

[0092]

change

[0093]

change

[0094]

change

[0095]

change

[0096]

change

[0097]

change

[0098]

change

[0099]

change

[0100]

change

[0101]

change

[0102]

change

[0103]

change

[0104]

change

[0105]

change

[0106]

change

[0107]

change

[0108]

change

[0109]

change

[0110]

change

[0111] [ka]

[0112] [ka]

[0113] [ka]

[0114] [ka]

[0115] [ka]

[0116] Preferably, A in the compound of formula (E-1) is

[0117] [ka]

[0118] (wherein the dotted bond indicates the bond from A to the rest of the formula) is.

[0119] Preferably, Z is

[0120] [ka]

[0121] If no groups are attached to it, CR 2 and when such a group is attached to it, it is C.

[0122] Preferably, two X groups in the ring in formula (E) are N and the third X group is CR 4 or all three X groups in the ring in formula (E) are N. More preferably, all three X groups in the ring in formula (E) are N.

[0123] Preferably,

[0124] [ka]

[0125] The group has the formula:

[0126] [ka]

[0127] where the dotted line represents the bond to the rest of the formula.

[0128] Preferably, Ar 2 are in each occurrence the same or different, preferably the same, and are selected from groups derived from benzene, cyanobenzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, indenofluorene, indenocarbazole, spirobifluorene, dibenzofuran, dibenzofuranyl-substituted benzenes, dibenzothiophene, dibenzothiophenyl-substituted benzenes, carbazole, carbazolyl-substituted benzenes, bis-N-carbazolyl-substituted benzenes, each of which may be selected from the group consisting of one or more R 5 radicals, more preferably selected from groups derived from benzene, cyanobenzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, dibenzofuran, dibenzofuranyl-substituted benzene, dibenzothiophene, dibenzothiophenyl-substituted benzene, and carbazole, each of which may be substituted by one or more R 5 Even more preferably, Ar2 is in each case one or more R 5 benzene substituted with a radical, in this case R 5 is especially selected from H and CN. Most preferred is unsubstituted benzene.

[0129] Ar 1 are preferably the same or different and are selected from divalent radicals derived from benzene, biphenyl, terphenyl, naphthalene, fluorene, indenofluorene, indenocarbazole, spirobifluorene, dibenzofuran, dibenzothiophene, and carbazole, each of which may be selected from one or more R 3 It may be substituted by a radical. Even more preferably, it is 1 is a divalent radical derived from benzene, biphenyl, and naphthyl, each of which may be one or more R 3 The radicals may be substituted, preferably unsubstituted, and are especially p-phenylene, o-phenylene, or m-phenylene, each of which may be one or more R 3 It may be substituted by a radical, preferably unsubstituted, and most preferably has one or more R 3 It is preferably unsubstituted p-phenylene, which may be substituted with a radical.

[0130] In a preferred embodiment, the subscript n is 0. In an alternative preferred embodiment, the subscript n is 1, 2 or 3, preferably 1 or 2, more preferably 1.

[0131] Preferred -(Ar 1 ) n - groups, especially -Ar 1 - is represented by the following formula:

[0132] [ka]

[0133] [ka]

[0134] [ka]

[0135] [ka]

[0136] (where the dotted line represents the bond to the rest of the formula). Among these, 1 -1)~(Ar 1 -9), (Ar 1 -15) and (Ar 1 -19) is particularly preferred.

[0137] Preferably, R 1 are in each case the same or different, preferably the same, H, D, F, CN, Si(R 6 )3, selected from linear alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy 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; the alkyl and alkoxy groups, the aromatic ring systems, and the heteroaromatic ring systems are each selected from R 6 one or more CH groups in the mentioned alkyl or alkoxy groups may be substituted by -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 More preferably, R 1are in each occurrence the same or different, preferably the same, and are selected from H, F, a linear 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, the aromatic ring system and the heteroaromatic ring system being each selected from R 6 Most preferably, R 1 are in each occurrence the same or different, preferably the same and selected from methyl and phenyl.

[0138] Preferably, R 2 are the same or different in each case and are H, D, F, CN, Si(R 6 )3, selected from linear alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy 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; the alkyl and alkoxy groups, the aromatic ring systems, and the heteroaromatic ring systems are each selected from R 6 one or more CH groups in the mentioned alkyl or alkoxy groups may be substituted by -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 More preferably, R 2 are the same or different in each occurrence and are selected from a linear alkyl group having 1 to 20 carbon atoms, a branched 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, and the alkyl group, the aromatic ring system, and the heteroaromatic ring system are each selected from R 6 Most preferably, R2 is H.

[0139] Preferably, R 3 are the same or different in each case and are H, D, F, CN, Si(R 6 )3, selected from linear alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy 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; the alkyl and alkoxy groups, the aromatic ring systems, and the heteroaromatic ring systems are each selected from R 6 one or more CH groups in the mentioned alkyl or alkoxy groups may be substituted by -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 - may be replaced by

[0140] Preferably, R 4 are the same or different in each case and are H, D, F, CN, Si(R 6 )3, a linear 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 selected from R 6 More preferably, R 4 are the same or different in each occurrence and have H and 6 to 40 aromatic ring atoms; R 6 Most preferably, R is selected from aromatic ring systems substituted by a radical. 4 are the same or different in each case, H, respectively R 6The radical is selected from phenyl, biphenyl, terphenyl and naphthyl, substituted by the radical.

[0141] Preferably, R 5 are the same or different in each case and are H, D, F, CN, Si(R 6 )3, selected from linear alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy 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; the alkyl and alkoxy groups, the aromatic ring systems, and the heteroaromatic ring systems are each selected from R 6 one or more CH groups in the mentioned alkyl or alkoxy groups may be substituted by -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 - may be replaced by

[0142] Preferably, R 6 are the same or different in each case and are H, D, F, CN, Si(R 7 )3, selected from linear alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy 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; the alkyl and alkoxy groups, the aromatic ring systems, and the heteroaromatic ring systems are each selected from R 7 one or more CH groups in the mentioned alkyl or alkoxy groups may be substituted by -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 - may be replaced by

[0143] The compound of formula (E) preferably has the following formula:

[0144] [ka]

[0145] [ka]

[0146] (wherein the symbols and subscripts occurring are as defined above and preferably correspond to the preferred embodiments thereof as specified above). Z is

[0147] [ka]

[0148] If no groups are attached to it, CR 2 and Z is C when such a group is attached thereto. 1 is preferably methyl or phenyl. Among the formulae (E-1) to (E-4), the formulae (E-1) and (E-2) are preferred, and the formula (E-1) is particularly preferred.

[0149] Preferred embodiments of formulas (E-1) to (E-4) are those represented by the following formula:

[0150] [ka]

[0151] [ka]

[0152] [ka]

[0153] [ka]

[0154] [ka]

[0155] [ka]

[0156] [ka]

[0157] (wherein the symbols and subscripts appearing are as defined above and preferably correspond to the preferred embodiments thereof as specified above). 2 )3 or -(R 2 )4 designation means that there are three or four R on the benzene ring in question. 2 group, i.e., one R at each unoccupied position on the benzene ring. 2 Preferably, for the formula, Ar 1 , Ar 2 , R 1 and R 2 The above preferred embodiments of the group Ar are applicable. 1 is phenyl or biphenyl, especially phenyl, and Ar 2 is phenyl or biphenyl, and R 1 is methyl or phenyl, and R 2 is H.

[0158] Among 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), especially formulas (E-1-1) to (E-1-4) are preferred. Among 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), especially formulas (E-1-2) and (E-1-4) are preferred.

[0159] - Ar 1 are the same or different and are selected from divalent radicals derived from benzene, biphenyl, terphenyl, naphthalene, fluorene, indenofluorene, indenocarbazole, spirobifluorene, dibenzofuran, dibenzothiophene, and carbazole, each of which is selected from one or more R 3 optionally substituted with radicals; - Ar 2 are in each occurrence the same or different, preferably the same, and are selected from the group derived from benzene, cyanobenzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, indenofluorene, indenocarbazole, spirobifluorene, dibenzofuran, dibenzofuranyl-substituted benzene, dibenzothiophene, dibenzothiophenyl-substituted benzene, carbazole, carbazolyl-substituted benzene, bis-N-carbazolyl-substituted benzene, each of which is selected from the group derived from one or more R 5 is substituted by a radical; -R 1 are the same or different in each occurrence and are selected from a linear alkyl group having 1 to 20 carbon atoms, a branched 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, and said alkyl group, said aromatic ring system, and said heteroaromatic ring system are each selected from R 6 is substituted by a radical; -R 2are the same or different in each occurrence and are selected from H, F, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; the aromatic ring systems and heteroaromatic ring systems are each selected from R 6 Substituted by a radical This is particularly preferred in the cases of formulae (E-1-1) to (E-4-4).

[0160] Preferred specific embodiments of compounds of formula (E) are selected from the following compounds:

[0161] [ka]

[0162] [ka]

[0163] [ka]

[0164] [ka]

[0165] [ka]

[0166] [ka]

[0167] [ka]

[0168] [ka]

[0169]

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[0170]

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[0171]

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[0172]

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[0173]

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[0174]

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[0175]

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[0176]

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[0177]

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[0178]

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[0179]

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[0180]

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[0181]

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[0182]

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[0183]

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[0184]

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[0185]

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[0186]

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[0187]

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[0188]

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[0189]

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[0190] [ka]

[0191] [ka]

[0192] [ka]

[0193] [ka]

[0194] [ka]

[0195] The layer containing the compound of formula (H) is preferably a hole transport layer.The compound of formula (H) may be present in the layer in pure form or in a mixture with another hole transport material or in a mixture with a p-dopant.Here, the other hole transport material is preferably selected from triarylamines, more preferably monotriarylamines, especially from the preferred hole transport materials explicitly listed below.

[0196] The p-dopants used in accordance with the present invention are preferably organic electron acceptor compounds capable of oxidizing one or more other compounds in the mixture.

[0197] Particularly preferred p-dopants are quinodimethane compounds, azaindenofluorenediones, azaphenalenes, azatriphenylenes, I2, metal halides, preferably transition metal halides, metal oxides, preferably metal oxides containing at least one transition metal or metal of the third main group, and transition metal complexes, preferably complexes of Cu, Co, Ni, Pd, and Pt with ligands containing at least one oxygen atom as a binding site. Transition metal oxides are also preferred as dopants, preferably oxides of rhenium, molybdenum, and tungsten, more preferably Re2O7, MoO3, WO3, and ReO3. Even more preferred are complexes of bismuth in the (III) oxidation state, more particularly bismuth(III) complexes with electron-deficient ligands, more particularly carboxylate ligands.

[0198] The p-dopant is preferably substantially uniformly distributed in the p-doped layer. This can be achieved, for example, by co-evaporation of the p-dopant with the hole transport material matrix. The p-dopant is preferably present in the p-doped layer in a proportion of 1% to 10%.

[0199] Preferred p-dopants are especially the following compounds:

[0200] [ka]

[0201] In addition to the layer containing the compound of formula (H), the electronic device may contain one or more further hole-transporting layers, hole-injecting layers, and electron-blocking layers. A preferred layer configuration of the electronic device is one in which there is a hole-injecting layer disposed side by side with the layer containing the compound of formula (H) directly adjacent to the anode, and there is an electron-blocking layer directly adjacent to the light-emitting layer on the anode side.

[0202] The hole injection layer preferably contains a hole transporting material, preferably a triarylamine, more preferably a compound selected from the specific embodiments of hole transporting materials specified below, and a p-dopant as defined above. In a preferred embodiment, the hole injection layer contains a compound of formula (H) as defined above, and a p-dopant as defined above.

[0203] In a further preferred embodiment, the hole injection layer contains a hexaazatriphenylene derivative, such as those described in US 2007 / 0092755, or another highly electron-deficient and / or Lewis acidic compound in pure form, i.e., not as a mixture with another compound. Examples of such compounds include bismuth complexes, especially Bi(III) complexes, especially Bi(III) carboxylates, such as compound D-14 above.

[0204] Preferably, the electronic device contains an electron-blocking layer immediately adjacent to the light-emitting layer on the anode side, the electron-blocking layer preferably containing a compound selected from triarylamines containing one or more fluorenyl or spirobifluorenyl groups.

[0205] Particularly preferred is a compound of formula (EBM)

[0206] [ka]

[0207] (In the formula, Y is the same or different in each occurrence and is O, S, or NR EBM1 Selected from; Ar 3 are the same or different in each occurrence 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 of which is selected from R EBM1 is substituted by a radical; k is 1, 2 or 3; i, in each occurrence, is the same or different and is selected from 0, 1, 2, and 3; The formula is R at each unoccupied position. EBM1 is substituted by a radical, R EBM1 are the same or different in each case and are 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 linear 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; two or more R EBM1 The radicals may be linked to each other or may form a ring; the mentioned alkyl, alkoxy, alkenyl and alkynyl groups, and the mentioned aromatic and heteroaromatic ring systems, are each R EBM2 one or more CH groups in the mentioned alkyl, alkoxy, alkenyl and alkynyl groups may be substituted by -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 ), -O-, -S-, SO or SO2; R EBM2 are the same or different in each case and are 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)REBM3 , S(=O)2R EBM3 , a linear 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; two or more R EBM2 The radicals may be linked to each other or may form a ring; the mentioned alkyl, alkoxy, alkenyl and alkynyl groups, and the mentioned aromatic and heteroaromatic ring systems, are each R EBM3 one or more CH groups in the mentioned alkyl, alkoxy, alkenyl and alkynyl groups may be substituted by -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 ), -O-, -S-, SO or SO2; R EBM3 are the same or different in each occurrence and are 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; EBM3 The radicals may be linked to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic and heteroaromatic ring systems mentioned may be substituted by one or more radicals selected from F and CN. is a compound of

[0208] Preferably, in formula (EBM), Y, at each occurrence, is the same or different and is selected from O and S, more preferably O. Even more preferably, k is 1 or 2. Even more preferably, i, at each occurrence, is the same or different and is selected from 1 and 2, more preferably 1.

[0209] Preferably, at least one Ar in formula (EBM) 3 , more preferably exactly one Ar in formula (EBM) 3 are R EBM1 The radical is selected from phenyl, biphenyl, terphenyl, fluorenyl-substituted phenyl, and spirobifluorenyl-substituted phenyl.

[0210] A preferred embodiment of formula (EBM) is the following formula:

[0211] [ka]

[0212] and the formula is R EBM1 In the above formulae (EBM-1) to (EBM-4), it is preferred that the fluorenyl or spirobifluorenyl group is bonded to the 1- or 4-position, more preferably to the 4-position:

[0213] [ka]

[0214] Compounds used as hole transport materials in electronic devices are, inter alia, indenofluoreneamine derivatives, amine derivatives, hexaazatriphenylene derivatives, amine derivatives with fused aromatic systems, monobenzoindenofluoreneamines, dibenzoindenofluoreneamines, spirobifluoreneamines, fluoreneamines, spirodibenzopyranamines, dihydroacridine derivatives, spirodibenzofurans and spirodibenzothiophenes, phenanthrene diarylamines, spirotribenzotropolones, spirobifluorenes with metaphenyldiamine groups, spirobisacridines, xanthenediarylamines, and 9,10-dihydroanthracene pyro-compounds with diarylamino groups.

[0215] Specific preferred compounds suitable for use in layers having hole transport functionality, in particular hole injection layers, hole transport layers and / or electron blocking layers, or as matrix materials in light-emitting layers, in particular light-emitting layers comprising one or more phosphorescent emitters, in electronic devices or OLEDs are shown in the table below:

[0216] [ka]

[0217] [ka]

[0218] [ka]

[0219] [ka]

[0220] [ka]

[0221] [ka]

[0222] [ka]

[0223] [ka]

[0224] Compounds HT-1 through HT-77 are generally well suited for use in OLEDs of any design and composition, as well as in the OLEDs of the present application. Further relevant disclosures regarding processes for preparing and using these compounds are disclosed in the published specifications cited in parentheses in the table below each compound. The compounds exhibit good performance data in OLEDs, particularly good lifetimes and efficiencies.

[0225] 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; instead, there is a hole-blocking layer between the light-emitting layer and the layer containing the compound of Formula (E), which is directly adjacent to the light-emitting layer.

[0226] In a preferred embodiment, the electronic device contains a hole-blocking layer directly adjacent to the light-emitting layer and an electron-transporting layer between the light-emitting layer and the cathode. In a preferred embodiment, an electron-injecting layer is present between the electron-transporting layer and the cathode, directly adjacent to the cathode. In an alternative preferred embodiment, such an electron-injecting layer is not present. In this case, the electron-transporting layer preferably contains an alkali metal salt, more preferably a lithium salt, in addition to the electron-transporting material. The alkali metal salt is preferably a salt with an organic anion, more preferably an 8-hydroxyquinolinate salt. Most preferably, the alkali metal salt is lithium 8-hydroxyquinolinate.

[0227] The electron transport layer of the electronic device preferably comprises a compound of formula (E).

[0228] The hole blocking layer preferably comprises a compound of formula (HBM).

[0229] [ka]

[0230] (In the formula, Ar HBM1 are the same or different in each occurrence and have 6 to 40 aromatic ring atoms; R HBM1 from an aromatic ring system substituted by a radical and having 5 to 40 aromatic ring atoms, R HBM1 a heteroaromatic ring system substituted by a radical; p is 0 or 1, and when p=0, the nitrogen atom and the Q group are directly bonded to each other; Q has 5 to 40 aromatic ring atoms, including at least one nitrogen atom as an aromatic ring atom, and R HBM2 an electron-deficient heteroaryl group substituted by a radical; R HBM1 are the same or different in each case and are 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 linear 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; two or more R HBM1The radicals may be linked to each other or may form a ring; the mentioned alkyl, alkoxy, alkenyl and alkynyl groups, and the mentioned aromatic and heteroaromatic ring systems, are each R HBM3 one or more CH groups in the mentioned alkyl, alkoxy, alkenyl and alkynyl groups may be substituted by -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 ), -O-, -S-, SO or SO2; R HBM2 are the same or different in each case and are 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 linear 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; two or more R HBM2 The radicals may be linked to each other or may form a ring; the mentioned alkyl, alkoxy, alkenyl and alkynyl groups, and the mentioned aromatic and heteroaromatic ring systems, are each R HBM3 one or more CH groups in the mentioned alkyl, alkoxy, alkenyl and alkynyl groups may be substituted by -R HBM3 C=CR HBM3 -, -C≡C-, Si(R HBM3 )2, C=O, C=NR HBM3 , -C(=O)O-, -C(=O)NR HBM3 -, NRHBM3 , P(=O)(R HBM3 ), -O-, -S-, SO or SO2; R HBM3 are the same or different in each occurrence and are 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; HBM3 The radicals may be bonded to one another or may form rings; the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic and heteroaromatic ring systems mentioned may be substituted by one or more radicals selected from F and CN; Spirobifluorene has R at each unoccupied position. HBM1 (substituted by radicals).

[0231] Preferably, Ar HBM1 is selected from divalent radicals derived from benzene, biphenyl, terphenyl, naphthalene, fluorene, indenofluorene, indenocarbazole, spirobifluorene, dibenzofuran, dibenzothiophene, and carbazole, each of which is selected from one or more R HBM1 It may be substituted by a radical. Even more preferably, it is HBM1 is a divalent radical derived from benzene, biphenyl, and naphthyl, each of which may be one or more R HBM1 The radicals may be substituted, preferably unsubstituted, and are especially p-phenylene, o-phenylene, or m-phenylene, each of which may be one or more R HBM1 It may be substituted by a radical, preferably unsubstituted, and most preferably has one or more R HBM1 It is preferably unsubstituted p-phenylene, which may be substituted with a radical.

[0232] Preferred Ar HBM1The group has the formula Ar 1 -1~Ar 1 -75 corresponds to the group shown above.

[0233] Preferably, the index p=0.

[0234] Preferably, Q is selected from groups containing at least one heteroaromatic six-membered ring containing at least one nitrogen atom as a ring atom or at least one aromatic five-membered ring containing at least two nitrogen atoms as ring atoms. The six-membered or five-membered rings mentioned may be fused to further rings. The heteroaromatic six-membered rings containing at least one nitrogen atom as a ring atom are especially selected from azines.

[0235] More preferably, each Q is R HBM2 Even more preferably, Q is selected from triazine, pyrimidine and quinazoline, each substituted by a radical. HBM2 Most preferably, Q is selected from triazine and pyrimidine, each substituted by a radical. HBM2 is a triazine substituted by a radical, in which case R HBM2 The radicals are preferably selected from aromatic ring systems having 6 to 40 aromatic ring atoms, especially phenyl, naphthyl, biphenyl, terphenyl, quaterphenyl and fluorenyl.

[0236] Preferred embodiments of the Q group include those represented by the formulae (Q-1) to (Q-5):

[0237] [ka]

[0238] (In the formula, the dotted line indicates a bond to the rest of the formula, and R in formulas (Q-1) to (Q-5) HBM2is preferably selected from aromatic ring systems having 6 to 40 aromatic ring atoms, especially selected from phenyl, naphthyl, biphenyl, terphenyl, quaterphenyl and fluorenyl. Among formulas (Q-1) to (Q-5), formulas (Q-1) to (Q-3) are preferred, with formula (Q-1) being most preferred.

[0239] Preferred embodiments of formula (HBM) include the following formulas (HBM-1) to (HBM-4):

[0240] [ka]

[0241] (wherein the spirobifluorene has R HBM1 The formula (HBM-1) is particularly preferred.

[0242] Preferred compounds of formula (HBM) are shown in the table below:

[0243] [ka]

[0244] [ka]

[0245] [ka]

[0246] [ka]

[0247] [ka]

[0248]

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[0249]

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[0250]

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[0251]

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[0252]

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[0253]

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[0254]

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[0255]

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[0256]

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[0257] 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 with an organic anion, more preferably an 8-hydroxyquinolinate salt. Most preferably, the alkali metal salt is lithium 8-hydroxyquinolinate (LiQ).

[0258] The electron injection layer preferably contains one or more compounds, preferably one compound, selected from LiQ, Yb, LiF, and CsF, and preferably has a thickness of 0.5 to 5 nm, particularly 1 to 3 nm.

[0259] The materials used in the layers between the light-emitting layer and the cathode, especially in the electron-transporting layer, may be any material used as an electron-transporting material in corresponding devices according to the prior art, particularly preferred 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, quinoline derivatives, oxadiazole derivatives, aromatic ketones, lactams, boranes, diazaphosphole derivatives and phosphine oxide derivatives.

[0260] Preferred specific embodiments of such compounds are shown in the table below:

[0261] [ka]

[0262] [ka]

[0263] [ka]

[0264] The electronic device is preferably selected from the group consisting of organic integrated circuits (OICs), organic field effect transistors (OFETs), organic thin film transistors (OTFTs), organic light emitting transistors (OLETs), organic solar cells (OSCs), organic optical detectors, organic photoreceptors, organic field quenched devices (OFQDs), organic light emitting electrochemical cells (OLECs), organic laser diodes (O-lasers), more preferably organic electroluminescent devices (OLEDs).

[0265] In addition to the cathode, the anode, the light-emitting layer, the layer containing the compound of Formula (H) and the layer containing the compound of Formula (E), the electronic device may contain further layers, for example, in each case selected 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, interlayers, charge generation layers, and / or organic or inorganic p / n junctions.

[0266] A preferred configuration of the electronic device is as follows: -anode -Hole injection layer a layer containing a compound of formula (H) as a hole transport layer - optionally a further hole transport layer -electron blocking layer -Emitting layer -Hole blocking layer a layer containing a compound of formula (E) as an electron transport layer -Optionally a further electron transport layer -Optionally, an electron injection layer -Cathode.

[0267] The light-emitting layer of the device may be a fluorescent light-emitting layer or a phosphorescent light-emitting layer. The light-emitting layer of the device is preferably a fluorescent light-emitting layer, particularly preferably a blue fluorescent light-emitting layer. In a fluorescent light-emitting layer, the emitter is preferably a singlet emitter, i.e., a compound that emits light from an excited singlet state when the device is operated. In a phosphorescent light-emitting layer, the emitter is preferably a triplet emitter, i.e., a compound that emits light from an excited triplet state or a state with a higher spin quantum number, such as a quintet state, when the device is operated.

[0268] In a preferred embodiment, the fluorescent light-emitting layer used is a blue-fluorescent layer.

[0269] In a preferred embodiment, the phosphorescent light-emitting layer used is a green or red phosphorescent light-emitting layer.

[0270] Suitable phosphorescent emitters are especially compounds which, when appropriately excited, preferably emit light in the visible region and which 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. As phosphorescent emitters, preference is given to using compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, especially compounds containing iridium, platinum or copper.

[0271] In general, all such phosphorescent complexes as are used in phosphorescent OLEDs according to the prior art and known to those skilled in the art of organic electroluminescent devices are suitable for use in the devices of the present invention.

[0272] Preferred fluorescent compounds are selected from the arylamine class. In the context of the present invention, arylamine or aromatic amine is understood to mean a compound 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 thereof are aromatic anthraceneamines, aromatic anthracenediamines, aromatic pyreneamines, aromatic pyrenediamines, aromatic chrysenamines or aromatic chrysenediamines.

[0273] Aromatic anthracenamines are understood to mean compounds in which a diarylamino group is directly bonded to an anthracene group, preferably in position 9. Aromatic anthracenediamines are understood to mean compounds in which two diarylamino groups are directly bonded to an anthracene group, preferably in positions 9 and 10. Aromatic pyrenamines, pyrenediamines, chrysenamines and chrysenediamines are similarly defined, in which the diarylamino groups are bonded to the pyrene, preferably in positions 1 or 1 and 6.

[0274] Further preferred luminescent compounds are indenofluorene amines or diamines, benzoindenofluorene amines or diamines, and dibenzoindenofluorene amines or diamines, as well as indenofluorene derivatives with fused aryl groups. Also preferred are pyrene arylamines. Also preferred are benzoindenofluorene amines, benzofluorene amines, extended benzoindenofluorenes, phenoxazines, and fluorene derivatives linked to furan or thiophene units.

[0275] Preferred compounds for use as fluorescent emitters are shown in the table below:

[0276] [ka]

[0277] [ka]

[0278] [ka]

[0279] [ka]

[0280] [ka]

[0281] [ka]

[0282] [ka]

[0283] [ka]

[0284] In a preferred embodiment, the light-emitting layer of the electronic device contains exactly one matrix compound. Matrix compound is understood to mean a compound that is not a light-emitting compound. This embodiment is particularly preferred in the case of a fluorescent light-emitting layer.

[0285] In an alternative preferred embodiment, the light-emitting layer of the electronic device contains exactly two or more, preferably exactly two, matrix compounds. This embodiment, also referred to as a mixed matrix system, is particularly preferred for phosphorescent light-emitting layers.

[0286] In the case of the phosphorescent light-emitting layer, the total proportion of all matrix materials is preferably 50.0% to 99.9%, more preferably 80.0% to 99.5%, and most preferably 85.0% to 97.0%.

[0287] Figures relating to proportions in % are understood here to mean proportions in % by volume in the case of layers applied from the gas phase and proportions in % by weight in the case of layers applied from solution.

[0288] Correspondingly, the proportion of the phosphorescent compound is preferably 0.1% to 50.0%, more preferably 0.5% to 20.0%, and most preferably 3.0% to 15.0%.

[0289] For the fluorescent-emitting layer, the total proportion of all matrix materials is preferably 50.0% to 99.9%, more preferably 80.0% to 99.5%, and most preferably 90.0% to 99.0%.

[0290] Correspondingly, the proportion of the fluorescent compound is 0.1% to 50.0%, preferably 0.5% to 20.0%, more preferably 1.0% to 10.0%.

[0291] The mixed matrix system preferably contains two or three different matrix materials, more preferably two different matrix materials. Preferably, in this case, one of the two materials has hole-transporting properties, and the other material has electron-transporting properties. A further matrix material that may be present in the mixed matrix system is a compound with a large energy difference between its HOMO and LUMO (wide bandgap material). 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 mixed matrix system is preferably used for phosphorescent organic electroluminescent devices.

[0292] Preferred matrix materials for fluorescent compounds are selected from the classes of oligoarylenes (e.g., 2,2',7,7'-tetraphenylspirobifluorene), especially oligoarylenes containing fused aromatic groups, oligoarylenevinylenes, polypodal metal complexes, hole-conducting compounds, electron-conducting compounds, especially ketones, phosphine oxides and sulfoxides; atropisomers, boronic acid derivatives, and benzanthracenes. Particularly preferred matrix materials are selected from the classes of oligoarylenes containing naphthalene, anthracene, benzanthracene, and / or pyrene, or atropisomers of these compounds, oligoarylenevinylenes, ketones, phosphine oxides, and sulfoxides. Very particularly preferred matrix materials are selected from the classes of oligoarylenes containing anthracene, benzanthracene, benzophenanthrene, and / or pyrene, or atropisomers of these compounds. An oligoarylene in the context of the present invention is understood to mean a compound in which at least three aryl or arylene groups are linked together.

[0293] Preferred matrix materials for fluorescent light-emitting compounds are shown in the table below:

[0294] [ka]

[0295] [ka]

[0296] [ka]

[0297] [ka]

[0298] 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-biscarbazolylbiphenyl), indolocarbazole derivatives, indenocarbazole derivatives, azacarbazole derivatives, bipolar matrix materials, silanes, azaboroles or boronic esters, triazine derivatives, zinc complexes, diazasilol or tetraazasilol derivatives, diazaphosphole derivatives, bridged carbazole derivatives, triphenylene derivatives, or lactams.

[0299] In preferred embodiments, the electronic device contains exactly one light-emitting layer.

[0300] In an alternative preferred embodiment, the electronic device contains multiple light-emitting layers, preferably two, three, or four light-emitting layers. This is especially preferred for white-light-emitting electronic devices.

[0301] Preferably, the light-emitting layer in this case has several emission maxima between 380 nm and 750 nm as a whole, so that the overall result is white light emission; in other words, various light-emitting compounds that can fluoresce or phosphoresce and emit blue, green, yellow, orange or red light are used in the light-emitting layer. Particularly preferred are three-layer systems, i.e., systems with three light-emitting layers, one of which in each case emits blue light, one of which in each case emits green light, and one of which in each case emits orange or red light. In an alternative embodiment, to generate white light, it may be possible to use individual light-emitting compounds that emit over a wide wavelength range, rather than multiple light-emitting compounds that emit colored light.

[0302] In a preferred embodiment of the present invention, the electronic device comprises two or three, preferably three, identical or different layer sequences stacked on top of one another, each of the layer sequences comprising the following layers: a hole injection layer, a hole transport layer, an electron blocking layer, an emissive layer, and an electron transport layer, and at least one, preferably all, of the layer sequences contains at least one emissive layer, a layer containing a compound of Formula (E), and a layer containing a compound of Formula (H).

[0303] A double layer consisting of adjacent n-CGL and p-CGL is preferably arranged between each layer sequence, with the n-CGL disposed on the anode side and the p-CGL disposed on the cathode side. Here, CGL refers to a charge generation layer. Materials used in such layers are known to those skilled in the art. The p-CGL is preferably a p-doped amine, and more preferably a material selected from the above-mentioned preferred structural classes of hole transport materials.

[0304] Preferred cathodes for electronic devices are metals, metal alloys, or multilayer structures composed of various metals with low work functions, 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 with silver, such as alloys composed of magnesium and silver. In multilayer structures, in addition to the metals mentioned, additional metals with relatively high work functions, such as Ag or Al, can also be used. In this case, metal combinations such as Ca / Ag, Mg / Ag, or Ba / Ag are commonly used. It may be preferable to introduce a thin intermediate layer of a material with a high dielectric constant between the metallic cathode and the organic semiconductor. Examples of materials useful for this purpose include alkali metal or alkaline earth metal fluorides, as well as the corresponding oxides or carbonates (e.g., LiF, Li2O, BaF2, MgO, NaF, CsF, Cs2CO3, etc.). Lithium quinolinate (LiQ) can also be used for this purpose. The thickness of this layer is preferably 0.5 to 5 nm.

[0305] Preferred anodes are materials with a high work function. Preferably, the anode has a work function of more than 4.5 eV vs. vacuum. First, metals with high redox potentials are suitable for this purpose, such as Ag, Pt or Au. Second, metal / metal oxide electrodes (e.g., Al / Ni / NiO x , Al / PtO x) may be preferred. Depending on the application, at least one of the electrodes must be transparent or partially transparent to allow either irradiation of the organic material (organic solar cells) or light emission (OLEDs, O-lasers). Preferred anode materials here are conductive mixed metal oxides. Indium tin oxide (ITO) or indium zinc oxide (IZO) are particularly preferred. Furthermore, conductively doped organic materials, especially conductively doped polymers, are preferred. In addition, 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.

[0306] During manufacturing, the device is properly structured (depending on the application), the contacts are connected, and finally sealed to eliminate the damaging effects of water and air.

[0307] In a preferred embodiment, the electronic device is characterized in that one or more layers are applied by sublimation, in which case the material is applied in a vacuum sublimation system at 10 -5 less than mbar, preferably 10 -6 It is applied by evaporation at an initial pressure of less than 10 mbar, but in this case the initial pressure can be lowered further, for example to 10 -7 It is also possible to have a pressure below mbar.

[0308] Likewise, electronic devices are preferred, characterized in that one or more layers are applied by the OVPD (organic vapor phase deposition) method or with the aid of carrier gas sublimation. In this case, the material is -5 It is applied at a pressure of between mbar and 1 bar. A special case of this method is the OVJP (organic vapor jet printing) method, in which the material is applied directly by a nozzle and is therefore structured.

[0309] In addition, electronic devices are preferred which are characterized in that one or more layers are produced from solution, for example by spin-coating, or by any printing method, such as screen printing, flexographic printing, nozzle printing or offset printing, but more preferably by LITI (Light Induced Thermal Imaging, Thermal Transfer Printing) or inkjet printing.

[0310] More preferably, the electronic device of the present invention is fabricated by applying one or more layers from solution and applying one or more layers by sublimation.

[0311] 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 cosmetic applications.

[0312] [example] 1) Methods for determining the HOMO energy The HOMO energy is determined by quantum chemical calculations. For this purpose, the software package "Gaussian16 (Rev.B.01)" (Gaussian Inc.) is used. The neutral singlet ground state is optimized at the B3LYP / 6-31G(d) level. The HOMO and LUMO values ​​are determined at the B3LYP / 6-31G(d) level for the B3LYP / 6-31G(d)-optimized ground state energy. TD-DFT singlet and triplet excitations (vertical excitations) are then calculated for the optimized ground state structure by the same method (B3LYP / 6-31G(d)). Standard settings for SCF and gradient convergence are used.

[0313] The energy calculation gives the HOMO in Hartree units as the last orbital occupied by two electrons (Alpha occ. eigenvalue), where HEh represents the HOMO energy in Hartree units, which is used to determine the HOMO value in electron volts calibrated by cyclic voltammetry measurements as follows: HOMO(eV)=(HEh*27.212)*0.8308-1.118 This value should be considered the HOMO of the material in the context of this application.

[0314] The following data are obtained for the compounds used:

[0315] [Table 1]

[0316] Therefore, the HOMO value of the compound used according to the present application is higher than the HOMO value of HTM-Ref.

[0317] 2) Method for determining hole mobility Glass plaques coated with 50 nm thick structured ITO (indium tin oxide) are treated with oxygen plasma followed by argon plasma before coating. These plasma-treated glass plaques form the substrate on which a 20 nm thick layer of the material to be analyzed, p-doped with F4TCNQ (concentration of p-dopant F4TCNQ = 5% by volume), is applied. A 100 nm thick layer of the material to be analyzed is applied to it by vapor deposition, followed by a 100 nm thick aluminum layer. The hole-only device (HOD) is then encapsulated. The current-voltage characteristics of the HOD are measured. The mobility can then be determined by applying the Mott-Gurney equation for space-charge-limited current to the current-voltage characteristics. In the following equation, μ0 is the hole mobility.

[0318]

number

[0319] J-current density V - Voltage minus built-in voltage L - thickness of the undoped HTM layer ε0 - Dielectric constant of vacuum ε - relative permittivity of the material being analyzed μ0-hole mobility

[0320] [Table 2]

[0321] 3) OLED component fabrication and analysis A) General Experimental Setup and Test Methods Glass plaques coated with 50 nm thick structured ITO (indium tin oxide) are treated with oxygen plasma followed by argon plasma before coating. These plasma-treated glass plaques form the substrates onto which the OLEDs are applied.

[0322] The OLED has the following layer structure: substrate / hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / emissive layer (EML) / optional hole blocking layer (HBL) / electron transport layer (ETL), and finally the cathode. The cathode is formed by a 100 nm thick aluminum layer. The exact structure of the OLED can be found in the table below. The materials required for the production of the OLED are listed in Table 5.

[0323] All materials are applied by thermal evaporation in a vacuum chamber. In this case, the emissive layer always consists of a matrix material and an emitter mixed (doped) into the matrix material in a specific volume fraction by co-evaporation. A figure given in the form SMB:SEB (95%:5%) means that the material SMB is present in the layer in a volume fraction of 95% and the material SEB in a volume fraction of 5%. The situation is similar for the electron transport layer.

[0324] The OLEDs are characterized by standard methods. For this purpose, the electroluminescence spectrum, the current efficiency (measured in cd / A) and the lifetime are determined. The electroluminescence spectrum is measured at 1000 cd / m 2 The luminance of the OLEDs analyzed is determined at 1000 cd / m², and the CIE 1931 x and y color coordinates are calculated from it. All OLEDs analyzed were 2 0.14 / 0.14 CIE x / y. CE1000 is 1000 cd / m2 The current efficiency achieved at 60mA / cm 2 It is defined as the time it takes for the brightness to decrease to 95% of the initial brightness when the device is operated at a constant current of 1000 kJ / s.

[0325] B) In a first experiment, an OLED containing HTM-Ref in the HTL (OLED C1) is compared to an otherwise identically structured OLED (OLED C2) that has compound HTM-1 in the HIL and HTL instead of HTM-Ref, or an otherwise identically structured OLED (OLED I2, I3, or I4) that has compound HTM-3, HTM-4, or HTM-5 in the HIL and HTL instead of HTM-Ref.

[0326] [Table 3]

[0327] OLED I1 shows a significant lifetime improvement (LT=60h) compared to OLED C1 (LT=30h). OLED I2 shows a lifetime improvement (LT=50h) compared to OLED C1 at the same efficiency. OLED I3 shows a lifetime improvement (LT=40h) compared to OLED C1 at the same efficiency. OLED I4 shows a lifetime improvement (LT=45h) compared to OLED C1 at the same efficiency.

[0328] C) In a second experiment, OLED I1 described above is compared with OLED I5, which differs from OLED I1 only in that it contains compound ETM-2 in the ETL rather than compound ETM-1.

[0329] [Table 4]

[0330] For OLED I5, an efficiency increase (CE1000=10.5) is obtained compared to OLED I1 (CE1000=10.1). The lifetime of I5 is slightly reduced compared to that of I1.

[0331] For the three other HTM materials HTM-3 to HTM-5, it is possible to obtain comparable results in this stack, especially improved efficiency.

[0332] D) In ​​a third experiment, OLED I5 described above is compared to OLED I6, which differs from OLED I5 only in that it contains compound EBM-2 in the EBL rather than compound EBM-1.

[0333] [Table 5]

[0334] This achieves a doubling of the lifetime of I6 (LT=80h) compared to I5 (LT=40h). The efficiency is constant to slightly higher, so this OLED clearly outperforms the other OLEDs in terms of the combined lifetime and efficiency properties.

[0335] For the three other HTM materials HTM-3 to HTM-5, it is possible to obtain comparable results in this stack, especially improved efficiency.

[0336] E) In a further experiment, an OLED is shown that includes compound HBM-1 in the HBL, where the HTM contains material HTM-3, the EBM contains material EBM-2, and the ETL contains material ETM-3.

[0337] [Table 6]

[0338] In this experiment, the best lifetime of all the OLEDs tested is obtained (LT=95 h) with a similar efficiency CE1000 to the other OLEDs tested, demonstrating the improvement that can be achieved by using compound HBM-1 in the HBL in combination with compounds in the HIL, HTL, EBL, and ETL.

[0339] [Table 7-1]

[0340] [Table 7-2]

[0341] [Table 7-3]

Claims

1. -Formula (H) 【Chemistry 1】 (In the formula, Ar Ｈ１ are the same or different in each occurrence and have 6 to 40 aromatic ring atoms; R Ｈ１ an aromatic ring system substituted by a radical, and having 5 to 40 aromatic ring atoms, R Ｈ１ heteroaromatic ring systems substituted by radicals; R Ｈ１ are in each case the same or different and are 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) ２ R Ｈ２ , a linear 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; Ｈ１ The radicals may be bonded to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups mentioned, and the aromatic and heteroaromatic ring systems mentioned, are each R Ｈ２ and substituted by one or more CH radicals in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned above. ２ The group is -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 ), —O—, —S—, SO or SO ２ may be replaced by; R Ｈ２ are in each case the same or different and are 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) ２ R Ｈ３ , a linear 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; Ｈ２ The radicals may be bonded to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups mentioned, and the aromatic and heteroaromatic ring systems mentioned, are each R Ｈ３ and substituted by one or more CH radicals in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned above. ２ The group is -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 ), —O—, —S—, SO or SO ２ may be replaced by; R Ｈ３ are the same or different in each occurrence and are 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; Ｈ３ The radicals may be linked to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems mentioned may be substituted by one or more radicals selected from F and CN. is present between the anode and the light-emitting layer; the compound of formula (H) has a HOMO of not lower than −4.72 eV, more preferably not lower than −4.71 eV, wherein the HOMO is determined by the method described in Examples Section 1; -Formula (E) 【Chemistry 2】 (In the formula, A is, 【Transformation 3】 where the dotted line indicates the connection to the rest of the formula; Z is 【Chemistry 4】 C, in each case the same or different, when a group is attached thereto; 【Transformation 5】 If no group is attached to it, CR ２ and N; X is the same or different in each occurrence, and N and CR ４ wherein at least one X is N; Ar １ are the same or different in each occurrence and have 6 to 40 aromatic ring atoms; R ３ an aromatic ring system substituted by a radical, and having 5 to 40 aromatic ring atoms, R ３ heteroaromatic ring systems substituted by radicals; Ar ２ are the same or different in each occurrence and have 6 to 40 aromatic ring atoms; R ５ an aromatic ring system substituted by a radical, and having 5 to 40 aromatic ring atoms, R ５ heteroaromatic ring systems substituted by radicals; R １ are in each case the same or different and are 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) ２ R ６ , a linear 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; １ The radicals may be bonded to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups mentioned, and the aromatic and heteroaromatic ring systems mentioned, are each R ６ and substituted by one or more CH radicals in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned above. ２ The group is -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 ), —O—, —S—, SO or SO ２ may be replaced by; R ２ are in each case the same or different and are 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) ２ R ６ , a linear 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; ２ The radicals may be bonded to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups mentioned, and the aromatic and heteroaromatic ring systems mentioned, are each R ６ and substituted by one or more CH radicals in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned above. ２ The group is -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 ), —O—, —S—, SO or SO ２ may be replaced by; R ３ are in each case the same or different and are 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) ２ R ６ , a linear 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; ３ The radicals may be bonded to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups mentioned, and the aromatic and heteroaromatic ring systems mentioned, are each R ６ and substituted by one or more CH radicals in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned above. ２ The group is -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 ), —O—, —S—, SO or SO ２ may be replaced by; R ４ are in each case the same or different and are 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) ２ R ６ , a linear 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; ４ The radicals may be bonded to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups mentioned, and the aromatic and heteroaromatic ring systems mentioned, are each R ６ and substituted by one or more CH radicals in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned above. ２ The group is -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 ), —O—, —S—, SO or SO ２ may be replaced by; R ５ are in each case the same or different and are 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) ２ R ６ , a linear 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; ５ The radicals may be bonded to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups mentioned, and the aromatic and heteroaromatic ring systems mentioned, are each R ６ and substituted by one or more CH radicals in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned above. ２ The group is -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 ), —O—, —S—, SO or SO ２ may be replaced by; R ６ are in each case the same or different and are 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) ２ R ７ , a linear 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; ６ The radicals may be bonded to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups mentioned, and the aromatic and heteroaromatic ring systems mentioned, are each R ７ and substituted by one or more CH radicals in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned above. ２ The group is -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 ), —O—, —S—, SO or SO ２ may be replaced by; R ７ are the same or different in each occurrence and are 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; ７ the radicals may be bonded to one another or may form rings; the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic and heteroaromatic ring systems mentioned may be substituted by one or more radicals selected from F and CN; n is 0, 1, 2, 3 or 4. is present between the light-emitting layer and the cathode.

1. An electronic device comprising an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, wherein:

2. Formula (H-1) or (H-2) 【Transformation 6】 wherein the spirobifluorenyl group, the fluorenyl group, and the optional phenylene group are each R Ｈ１ It may be substituted with a radical, and in addition: Ar Ｈ１ are the same or different in each occurrence and have 6 to 40 aromatic ring atoms; R Ｈ１ an aromatic ring system substituted by a radical, and having 5 to 40 aromatic ring atoms, R Ｈ１ heteroaromatic ring systems substituted by radicals; R Ｈ１ are in each case the same or different and are 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) ２ R Ｈ２ , a linear 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; Ｈ１ The radicals may be bonded to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups mentioned, and the aromatic and heteroaromatic ring systems mentioned, are each R Ｈ２ and substituted by one or more CH radicals in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned above. ２ The group is -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 ), —O—, —S—, SO or SO ２ may be replaced by; R Ｈ２ are in each case the same or different and are 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) ２ R Ｈ３ , a linear 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; Ｈ２ The radicals may be bonded to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups mentioned, and the aromatic and heteroaromatic ring systems mentioned, are each R Ｈ３ and substituted by one or more CH radicals in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned above. ２ The group is -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 ), —O—, —S—, SO or SO ２ may be replaced by; R Ｈ３ are the same or different in each occurrence and are 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; Ｈ３ the radicals may be bonded to one another or may form rings; the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic and heteroaromatic ring systems mentioned may be substituted by one or more radicals selected from F and CN; m is 0, 1, 2 or 3; attached to the aromatic ring of the spirobifluorenyl group or of the fluorenyl group, and having 1 to 20 carbon atoms, R Ｈ２ a linear alkyl group substituted by a radical, having 3 to 20 carbon atoms, R Ｈ２ a branched or cyclic alkyl group substituted with a radical, and 6 to 40 aromatic ring atoms, R Ｈ２ At least one R selected from an aromatic ring system substituted by a radical Ｈ１ exists) is present between the anode and the light-emitting layer, and -Formula (E) 【Transformation 7】 (In the formula, A is, 【Transformation 8】 where the dotted line indicates the connection to the rest of the formula; Z is 【Chemistry 9】 C, in each case the same or different, when a group is attached thereto; 【Chemistry 10】 If no group is attached to it, CR ２ and N; X is the same or different in each occurrence, and N and CR ４ wherein at least one X is N; Ar １ are the same or different in each occurrence and have 6 to 40 aromatic ring atoms; R ３ an aromatic ring system substituted by a radical, and having 5 to 40 aromatic ring atoms, R ３ heteroaromatic ring systems substituted by radicals; Ar ２ are the same or different in each occurrence and have 6 to 40 aromatic ring atoms; R ５ an aromatic ring system substituted by a radical, and having 5 to 40 aromatic ring atoms, R ５ heteroaromatic ring systems substituted by radicals; R １ are in each case the same or different and are 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) ２ R ６ , a linear 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; １ The radicals may be bonded to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups mentioned, and the aromatic and heteroaromatic ring systems mentioned, are each R ６ and substituted by one or more CH radicals in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned above. ２ The group is -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 ), —O—, —S—, SO or SO ２ may be replaced by; R ２ are in each case the same or different and are 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) ２ R ６ , a linear 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; ２ The radicals may be bonded to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups mentioned, and the aromatic and heteroaromatic ring systems mentioned, are each R ６ and substituted by one or more CH radicals in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned above. ２ The group is -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 ), —O—, —S—, SO or SO ２ may be replaced by; R ３ are in each case the same or different and are 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) ２ R ６ , a linear 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; ３ The radicals may be bonded to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups mentioned, and the aromatic and heteroaromatic ring systems mentioned, are each R ６ and substituted by one or more CH radicals in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned above. ２ The group is -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 ), —O—, —S—, SO or SO ２ may be replaced by; R ４ are in each case the same or different and are 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) ２ R ６ , a linear 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; ４ The radicals may be bonded to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups mentioned, and the aromatic and heteroaromatic ring systems mentioned, are each R ６ and substituted by one or more CH radicals in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned above. ２ The group is -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 ), —O—, —S—, SO or SO ２ may be replaced by; R ５ are in each case the same or different and are 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) ２ R ６ , a linear 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; ５ The radicals may be bonded to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups mentioned, and the aromatic and heteroaromatic ring systems mentioned, are each R ６ and substituted by one or more CH radicals in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned above. ２ The group is -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 ), —O—, —S—, SO or SO ２ may be replaced by; R ６ are in each case the same or different and are 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) ２ R ７ , a linear 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; ６ The radicals may be bonded to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups mentioned, and the aromatic and heteroaromatic ring systems mentioned, are each R ７ and substituted by one or more CH radicals in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned above. ２ The group is -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 ), —O—, —S—, SO or SO ２ may be replaced by; R ７ are the same or different in each occurrence and are 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; ７ the radicals may be bonded to one another or may form rings; the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic and heteroaromatic ring systems mentioned may be substituted by one or more radicals selected from F and CN; n is 0, 1, 2, 3 or 4. is present between the light-emitting layer and the cathode.

1. An electronic device comprising an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, wherein:

3. The compound of formula (H) is 2*10 －４ ~8*10 －４ cm ２ 3. A device according to claim 1 or 2, characterized in that it has a hole mobility of / Vs, the hole mobility being determined e.g. as specified in section 2).

4. The R Ｈ１ At least one Ar containing and substituted with a radical Ｈ１ 4. A device according to any one of claims 1 to 3, characterized in that the group contains a spirofluorenyl or fluorenyl group, preferably a 2-spirofluorenyl or 2-fluorenyl group.

5. Ar Ｈ１ and R Ｈ２ a linear alkyl group substituted by a radical, having 3 to 20 carbon atoms, R Ｈ２ a branched or cyclic alkyl group substituted with a radical, and 6 to 40 aromatic ring atoms, R Ｈ２ At least one R selected from an aromatic ring system substituted by a radical Ｈ１ 5. The device according to claim 1, wherein is present in said compound of formula (H).

6. R Ｈ１ are in each occurrence the same or different and are selected from H, D, F, CN, a linear 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 selected from R Ｈ２ 6. The device according to claim 1, characterized in that it is substituted by a radical.

7. R Ｈ２ are in each occurrence the same or different and are selected from H, a linear 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; and the alkyl group and the aromatic ring system each have R Ｈ３ 7. The device according to claim 1, characterized in that it is substituted by a radical.

8. Formula (H) is represented by formulas (H-1-1-a) to (H-1-1-p) 【Chemistry 11-1】 【Chemistry 11-2】 【Chemistry 11-3】 (In the formula, R Ｈ１－１ are the same or different in each occurrence and are selected from linear 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; the alkyl groups mentioned and the aromatic ring systems mentioned are each R Ｈ２ the other variables are as defined in any one of claims 1 to 7, and the spirobifluorenyl and phenylene groups are substituted with R which is preferably H at each unoccupied position. Ｈ１ substituted by radicals) 8. A device according to any one of claims 1 to 7, characterized in that it conforms to one of the following:

9. A in the compound of formula (E-1) is 【Chemistry 12】 (wherein the dotted bond indicates the bond from A to the rest of the formula) 9. The device according to claim 1, wherein: 【Request Item 10】 【Chemistry 13】 The group has the formula: 【Chemistry 14】 where the dotted line represents the bond to the rest of the formula.

10. A device according to any one of claims 1 to 9, characterized in that it conforms to

11. Ar ２ in each case one or more R ５ benzene substituted with a radical, in which case R ５ 11. Device according to any one of claims 1 to 10, characterized in that is selected in particular from H and CN.

12. Ar １ is a divalent radical derived from benzene, biphenyl, and naphthyl, each of which is represented by one or more R ３ The device according to any one of claims 1 to 11, which is optionally substituted by radicals.

13. -R １ are in each occurrence the same or different, preferably the same, and are selected from H, F, a linear 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, said aromatic ring system and said heteroaromatic ring system each being selected from R ６ is substituted by a radical, -R ２ are the same or different in each occurrence and are selected from a linear alkyl group having 1 to 20 carbon atoms, a branched 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 said alkyl group, said aromatic ring system, and said heteroaromatic ring system are each selected from R ６ is substituted by a radical, -R ３ are in each case the same or different, H, D, F, CN, Si(R ６ ) ３ , a linear 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 said alkyl and alkoxy groups, said aromatic ring system and said heteroaromatic ring system are each selected from R ６ and one or more of the alkyl or alkoxy groups mentioned are substituted by a radical; ２ The group is —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 - may be replaced by -R ４ are the same or different in each occurrence and have H and 6 to 40 aromatic ring atoms; R ６ is selected from aromatic ring systems substituted by radicals, -R ５ are in each case the same or different, H, D, F, CN, Si(R ６ ) ３ , a linear 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 said alkyl and alkoxy groups, said aromatic ring system and said heteroaromatic ring system are each selected from R ６ and one or more of the alkyl or alkoxy groups mentioned are substituted by a radical; ２ The group is —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 - may be replaced by -R ６ are in each case the same or different, H, D, F, CN, Si(R ７ ) ３ , a linear 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 said alkyl and alkoxy groups, said aromatic ring system and said heteroaromatic ring system are each selected from R ７ and one or more of the alkyl or alkoxy groups mentioned are substituted by a radical; ２ The group is —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 may be replaced by Device according to any one of claims 1 to 12, characterized in that it

14. The formula (E) is the following formula: 【Chemistry 15-1】 【Chemistry 15-2】 【Chemistry 15-3】 【Chemistry 15-4】 【Chemistry 15-5】 【Chemistry 15-6】 【Chemistry 15-7】 【Chemistry 15-8】 (wherein the symbols and subscripts appearing are as defined in any one of claims 1 to 18) 14. A device according to any one of claims 1 to 13, characterized in that it conforms to one of the following:

15. -Ar １ are the same or different and are selected from divalent radicals derived from benzene, biphenyl, terphenyl, naphthalene, fluorene, indenofluorene, indenocarbazole, spirobifluorene, dibenzofuran, dibenzothiophene, and carbazole, each of which is selected from one or more R ３ may be substituted by a radical; ２ are in each occurrence the same or different, preferably the same, and are selected from the group derived from benzene, cyanobenzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, indenofluorene, indenocarbazole, spirobifluorene, dibenzofuran, dibenzofuranyl-substituted benzene, dibenzothiophene, dibenzothiophenyl-substituted benzene, carbazole, carbazolyl-substituted benzene, bis-N-carbazolyl-substituted benzene, each of which is selected from the group derived from one or more R ５ is substituted by a radical; -R １ are the same or different in each occurrence and are selected from a linear alkyl group having 1 to 20 carbon atoms, a branched 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 said alkyl group, said aromatic ring system, and said heteroaromatic ring system are each selected from R ６ is substituted by a radical; -R ２ are the same or different in each occurrence and are selected from H, F, an aromatic ring system having 6 to 40 aromatic ring atoms, and a heteroaromatic ring system having 5 to 40 aromatic ring atoms; said aromatic ring system and said heteroaromatic ring system are each selected from R ６ Substituted by a radical 15. The device according to claim 14, characterized in that

16. The device according to any one of claims 1 to 15, characterized in that the layer containing the compound of formula (H) is a hole transporting layer.

17. 17. The device of claim 1, wherein there is a hole-injecting layer immediately adjacent to the anode and disposed alongside the layer containing the compound of formula (H), and there is an electron-blocking layer immediately adjacent to the light-emitting layer on the anode side.

18. 18. The device of claim 1, further comprising an electron blocking layer immediately adjacent to the light-emitting layer on the anode side, the electron blocking layer comprising a compound selected from triarylamines containing one or more fluorenyl or spirobifluorenyl groups.

19. an electron blocking layer directly adjacent to the light-emitting layer on the anode side, the electron blocking layer having the formula (EBM) 【Chemistry 16】 (In the formula, Y in each occurrence is the same or different and is selected from the group consisting of O, S and NR ＥＢＭ１ Selected from: Ar ３ are the same or different in each occurrence 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 of which is selected from R ＥＢＭ１ is substituted by a radical; k is 1, 2 or 3; i, in each occurrence, is the same or different and is selected from 0, 1, 2, and 3; The formula has R at each unoccupied position. ＥＢＭ１ is substituted by a radical, R ＥＢＭ１ are in each case the same or different and are 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) ２ R ＥＢＭ２ , a linear 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; ＥＢＭ１ The radicals may be bonded to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups mentioned, and the aromatic and heteroaromatic ring systems mentioned, are each R ＥＢＭ２ and substituted by one or more CH radicals in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned above. ２ The group is -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 ), —O—, —S—, SO or SO ２ may be replaced by; R ＥＢＭ２ are in each case the same or different and are 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) ２ R ＥＢＭ３ , a linear 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; ＥＢＭ２ The radicals may be bonded to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups mentioned, and the aromatic and heteroaromatic ring systems mentioned, are each R ＥＢＭ３ and substituted by one or more CH radicals in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned above. ２ The group is -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 ), —O—, —S—, SO or SO ２ may be replaced by; R ＥＢＭ３ are the same or different in each occurrence and are 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; ＥＢＭ３ The radicals may be linked to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems mentioned may be substituted by one or more radicals selected from F and CN.

19. A device according to any one of claims 1 to 18, characterized in that it comprises a compound of the formula:

20. Between the light-emitting layer and the cathode, a hole-blocking layer immediately adjacent to the light-emitting layer, and an electron-transporting layer, the hole-blocking layer having a structure represented by the formula (HBM): 【Chemistry 17】 (In the formula, Ar ＨＢＭ１ are the same or different in each occurrence and have 6 to 40 aromatic ring atoms; R ＨＢＭ１ from an aromatic ring system substituted by a radical and having 5 to 40 aromatic ring atoms, R ＨＢＭ１ heteroaromatic ring systems substituted by radicals; p is 0 or 1, and when p=0, the nitrogen atom and the Q group are directly bonded to each other; Q has 5 to 40 aromatic ring atoms, including at least one nitrogen atom as an aromatic ring atom, and R ＨＢＭ２ an electron-deficient heteroaryl group substituted by a radical; R ＨＢＭ１ are in each case the same or different and are 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) ２ R ＨＢＭ３ , a linear 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; ＨＢＭ１ The radicals may be bonded to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups mentioned, and the aromatic and heteroaromatic ring systems mentioned, are each R ＨＢＭ３ and substituted by one or more CH radicals in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned above. ２ The group is -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 ), —O—, —S—, SO or SO ２ may be replaced by; R ＨＢＭ２ are in each case the same or different and are 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) ２ R ＨＢＭ３ , a linear 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; ＨＢＭ２ The radicals may be bonded to each other or may form a ring; the alkyl, alkoxy, alkenyl and alkynyl groups mentioned, and the aromatic and heteroaromatic ring systems mentioned, are each R ＨＢＭ３ and substituted by one or more CH radicals in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned above. ２ The group is -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 ), —O—, —S—, SO or SO ２ may be replaced by; R ＨＢＭ３ are the same or different in each occurrence and are 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; ＨＢＭ３ the radicals may be bonded to one another or may form rings; the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic and heteroaromatic ring systems mentioned may be substituted by one or more radicals selected from F and CN; Spirobifluorene has R at each unoccupied position. ＨＢＭ１ substituted by radicals) 20. The device according to claim 1, comprising a compound of formula:

21. A device according to any one of claims 1 to 20, characterized in that it is an organic electroluminescent device.

22. 22. The device according to claim 1, wherein the light-emitting layer of the device is a blue fluorescent light-emitting layer.

23. A method for manufacturing a device according to any one of claims 1 to 22, characterized in that one or more layers of said device are applied by sublimation.

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