Compound, material for organic electroluminescent element, organic electroluminescent element and electronic device

Abstract

The compound represented by the following formula (1) provides an organic electroluminescent device with a further improved lifespan. 1 ~R 9 , R 11 ~R 18 , R 21 ~R 27 ,Ar,L 1 , L 2 and L 3 Same as the definition in the manual. #imgabs0#

Description

Technical Field

[0001] The present invention relates to a compound, a material for an organic electroluminescent element containing the compound, an organic electroluminescent element containing the compound, and an electronic device containing the organic electroluminescent element. Background Art

[0002] Generally speaking, an organic electroluminescent element (organic EL element) is composed of an anode, a cathode, and an organic layer sandwiched between the anode and the cathode. If a voltage is applied between the two electrodes, electrons are injected from the cathode side to the luminescent region, and holes are injected from the anode side to the luminescent region, and the injected electrons and holes are recombined in the luminescent region to generate an excited state, and light is emitted when the excited state returns to the ground state. Therefore, it is important to develop compounds that efficiently transmit electrons or holes to the luminescent region and promote the recombination of electrons and holes in order to obtain high-performance organic EL elements.

[0003] Patent Document 1 discloses an amine compound in which one 4-biphenyl group having an N-carbazolyl group at the ortho position of a terminal phenyl group and two aryl groups are bonded to a central nitrogen atom directly or via a linking group.

[0004] Patent Document 2 discloses an amine compound in which one 2-(N-carbazolyl)phenyl group, one 2-dibenzofuranyl group, and one group having an azine ring or an aryl group having an azine ring are bonded to a central nitrogen atom.

[0005] Patent Document 3 discloses an amine compound in which one 4-biphenyl group having an N-carbazoly group at the ortho position of a terminal phenyl group and two 4-biphenyl groups are bonded to a central nitrogen atom.

[0006] Patent Document 4 discloses an amine compound in which one 4-biphenyl group having an N-carbazolyl group at the meta-position of a terminal phenyl group, one 4-(4-dibenzofuranyl)phenyl group and one 4-biphenyl group are bonded to a central nitrogen atom.

[0007] Prior art literature

[0008] Patent Literature

[0009] Patent Document 1: International Publication No. 2017 / 052261A1

[0010] Patent Document 2: Korean Publication No. 10-2017-0072041

[0011] Patent Document 3: U.S. Patent Publication No. 2016 / 0322580A1

[0012] Patent Document 4: U.S. Patent Publication No. 2016 / 0079542A1 Summary of the invention

[0013] Problem that the invention aims to solve

[0014] Conventionally, many compounds have been reported as materials for producing organic EL devices, but there is still a demand for compounds that further improve the characteristics of organic EL devices.

[0015] The present invention has been made to solve the above-mentioned problems, and an object of the present invention is to provide an organic EL element having a further improved lifespan and a novel compound for realizing such an organic EL element.

[0016] Means used to solve problems

[0017] The present inventors have conducted intensive studies to achieve the above-mentioned object and have found that a compound represented by the following formula (1) can realize an organic EL device having a further improved lifespan.

[0018] In one embodiment, the present invention provides a compound represented by formula (1) (hereinafter sometimes referred to as compound (1)).

[0019] [Chemistry 1]

[0020]

[0021] (In formula (1),

[0022] R 7 , R 8 and R 9 One of them is a single bond to *a;

[0023] R 1 ~R 6 and R which is not a single bond to *a 7 ~R 9 each independently represents a hydrogen atom or a substituent selected from the group consisting of a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 36 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,

[0024] Among them, selected from R 1 ~R 6 and R which is not a single bond to *a 7 ~R9 Two adjacent ones of the group each independently represent a hydrogen atom or the above-mentioned substituent, or are bonded to each other to form a ring structure;

[0025] R 11 ~R 18 each independently represents a hydrogen atom or a substituent selected from the group consisting of a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 36 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,

[0026] Among them, selected from R 11 ~R 18 Two adjacent ones of the group each independently represent a hydrogen atom or the above-mentioned substituent, or are bonded to each other to form a ring structure;

[0027] R 21 ~R 27 each independently represents a hydrogen atom or a substituent selected from the group consisting of a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 36 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,

[0028] Among them, selected from R 21 ~R 27 Two adjacent ones of the group each independently represent a hydrogen atom or the above-mentioned substituent, or are bonded to each other to form a ring structure;

[0029] Ar is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms;

[0030] L 1 is a single bond or L 11 , L11 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms;

[0031] L 2 is a single bond or L 22 , L 22 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms;

[0032] L 3 is a single bond or L 33 , L 33 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms.

[0033] In another embodiment, the present invention provides a material for an organic electroluminescent device comprising the compound (1).

[0034] In another embodiment, the present invention provides an organic electroluminescent element, which is an organic electroluminescent element having a cathode, an anode, and an organic layer disposed between the cathode and the anode, wherein the organic layer includes a light-emitting layer, and at least one layer of the organic layer includes compound (1).

[0035] In yet another embodiment, the present invention provides an electronic device comprising the organic electroluminescent element.

[0036] Effects of the Invention

[0037] The compound (1) realizes an organic EL device having a further improved lifespan. BRIEF DESCRIPTION OF THE DRAWINGS

[0038] Figure 1 It is a schematic diagram showing an example of the layer structure of the organic EL element according to one embodiment of the present invention.

[0039] Figure 2 It is a schematic diagram showing another example of the layer structure of the organic EL element according to one embodiment of the present invention. DETAILED DESCRIPTION

[0040] In the present specification, "carbon number XX to YY" in the expression "substituted or unsubstituted ZZ group having carbon number XX to YY" means the carbon number of the ZZ group when it is unsubstituted, and does not include the carbon number of the substituent when it is substituted.

[0041] In the present specification, "the number of atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having the number of atoms XX to YY" means the number of atoms of the ZZ group when it is unsubstituted, and does not include the number of atoms of a substituent when it is substituted.

[0042] In the present specification, when referring to a "substituted or unsubstituted ZZ group", an "unsubstituted ZZ group" means that a hydrogen atom of the ZZ group is not substituted by a substituent.

[0043] In this specification, the term "hydrogen atom" includes isotopes having different numbers of neutrons, namely, protium, deuterium, and tritium.

[0044] In this specification, "ring carbon number" means the number of carbon atoms among the atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, a heterocyclic compound) whose atoms are bonded to form a ring structure. In the case where the ring is substituted by a substituent, the carbon contained in the substituent is not included in the ring carbon. The "ring carbon number" described below has the same meaning unless otherwise specified. For example, the ring carbon number of the benzene ring is 6, the ring carbon number of the naphthalene ring is 10, the ring carbon number of the pyridine ring is 5, and the ring carbon number of the furan ring is 4. In addition, in the case where, for example, an alkyl group is substituted as a substituent on the benzene ring or the naphthalene ring, the carbon number of the alkyl group is not included in the number of ring carbon numbers. In addition, in the case where, for example, a fluorene ring is bonded as a substituent on the fluorene ring (including a spirofluorene ring), the carbon number of the fluorene ring as a substituent is not included in the number of ring carbon numbers.

[0045] In this specification, "ring atoms" means the number of atoms constituting the ring itself of a compound (e.g., monocyclic compound, condensed ring compound, bridged compound, carbocyclic compound, heterocyclic compound) in which atoms are bonded to form a cyclic structure (e.g., monocyclic, condensed ring, aggregated ring). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the connecting bonds of atoms constituting the ring) and atoms contained in the substituent when the ring is substituted by a substituent are not included in the number of ring atoms. The "ring atoms" described below have the same meaning unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. Hydrogen atoms bonded to the ring carbon atoms of the pyridine ring and the quinazoline ring, respectively, and atoms constituting the substituent are not included in the number of ring atoms. In addition, in the case where a fluorene ring, such as a fluorene ring (including a spirofluorene ring) is bonded to the fluorene ring as a substituent, the number of atoms of the fluorene ring as a substituent is not included in the number of ring atoms.

[0046] The compound (1) according to one embodiment of the present invention is represented by formula (1).

[0047] [Chemistry 2]

[0048]

[0049] In one embodiment of the present invention, the compound (1) is preferably represented by the following formula (2).

[0050] [Chemistry 3]

[0051]

[0052] In one embodiment of the present invention, the compound (1) is preferably represented by any one of the following formulae (3) to (6).

[0053] [Chemistry 4]

[0054]

[0055] [Chemistry 5]

[0056]

[0057] [Chemistry 6]

[0058]

[0059] [Chemistry 7]

[0060]

[0061] In one embodiment of the present invention, compound (1) is preferably represented by the above formula (3) or (4).

[0062] Hereinafter, each symbol of Formulas (1) to (6) and Formulas (7) to (12) described later will be described.

[0063] R 7 , R 8 and R 9 One of them is a single bond to *a. That is, compound (1) is R 7 A compound having a single bond bonded to *a, R 8 is a compound having a single bond bonded to *a, or R 9 A compound having a single bond bonded to *a. 7 or R 8 A compound having a single bond bonded to *a, more preferably R 7 A compound having a single bond bonded to *a.

[0064] R 7 The compound having a single bond bonded to *a is represented by the following formula (7).

[0065] [Chemistry 8]

[0066]

[0067] Formula (7) is preferably represented by the following formula (8).

[0068] [Chemistry 9]

[0069]

[0070] R 8 The compound having a single bond bonded to *a is represented by the following formula (9).

[0071] [Chemistry 10]

[0072]

[0073] Formula (9) is preferably represented by the following formula (10).

[0074] [Chemistry 11]

[0075]

[0076] R 9 The compound having a single bond bonded to *a is represented by the following formula (11).

[0077] [Chemistry 12]

[0078]

[0079] Formula (11) is preferably represented by the following formula (12).

[0080] [Chemistry 13]

[0081]

[0082] R 1 ~R 6 and R which is not a single bond to *a 7 ~R 9Each is independently a hydrogen atom or a substituent selected from a halogen atom; a cyano group; a nitro group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, and more preferably 1 to 8 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, preferably 3 to 10 ring carbon atoms, more preferably 3 to 8 ring carbon atoms, and more preferably 5 or 6 ring carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, preferably 6 to 25 ring carbon atoms, and more preferably 6 to 18 ring carbon atoms; a substituted or unsubstituted aralkyl group having 7 to 36 ring carbon atoms, preferably 7 to 26 ring carbon atoms, and more preferably 7 to 20 ring carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 30 ring carbon atoms, preferably 1 to 18 ring carbon atoms, and more preferably 1 to 8 ring carbon atoms; a substituted or unsubstituted cycloalkyl group having 6 to 30 ring carbon atoms, preferably 3 to 10 ring carbon atoms, and more preferably 3 to 8 ring carbon atoms; The group consisting of: a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, and more preferably 6 to 18 carbon atoms; a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, and more preferably 6 to 18 carbon atoms in the ring; a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, and more preferably 1 to 8 carbon atoms; a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, and more preferably 1 to 8 carbon atoms; and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, preferably 5 to 24 ring atoms, and more preferably 5 to 13 ring atoms.

[0083] Among them, selected from R 1 ~R 6 and R which is not a single bond to *a 7 ~R 9 In the formula, the adjacent two independently represent a hydrogen atom or the above-mentioned substituent, or the adjacent two are bonded to each other to form a ring structure. That is, the adjacent two do not form a ring structure but independently represent a hydrogen atom or the above-mentioned substituent, or are bonded to each other to form a ring structure.

[0084] That is, R 1 ~R 6 and R which is not a single bond to *a 7 ~R 9 Each independently represents a hydrogen atom or a substituent, or is selected from R 1 ~R 9 Adjacent groups are bonded to form a ring structure.

[0085] The substituent is preferably selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; more preferably selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.

[0086] In one embodiment of the present invention, selected from R 1 ~R 6 and R which is not a single bond to *a 7 ~R 9 The two adjacent ones in the above do not form a ring structure but each independently represents a hydrogen atom or the above substituent. In another embodiment of the present invention, at least one set of the above two adjacent ones are bonded to each other to form a ring structure.

[0087] The halogen atom is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, and is preferably a fluorine atom.

[0088] Among the above-mentioned substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, the alkyl group having 1 to 30 carbon atoms is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl or dodecyl, preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or pentyl, more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, further preferably methyl or tert-butyl.

[0089] The above-mentioned substituted or unsubstituted alkyl group having 1 to 30 carbon atoms includes isomeric groups when present.

[0090] In the above-mentioned substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, the cycloalkyl group having 3 to 30 ring carbon atoms is, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, preferably cyclopentyl or cyclohexyl.

[0091] The above-mentioned substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms includes isomeric groups when it exists.

[0092] In the above-mentioned substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, the aryl group having 6 to 30 ring carbon atoms is, for example, phenyl, biphenyl, terphenyl, biphenylalkenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, triphenylenyl, phenanthren ... Benzo The invention relates to a phenyl group, a fluorenyl group, a fluorenyl group, a peryl group, or a triphenylene group, preferably a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, more preferably a phenyl group, a 2-biphenyl group, a 3-biphenyl group, or a 4-biphenyl group, a 2-o-terphenyl group, a 3-o-terphenyl group, or a 4-o-terphenyl group, a 2-m-terphenyl group, a 3-m-terphenyl group, or a 4-m-terphenyl group, a 2-p-terphenyl group, a 3-p-terphenyl group, or a 4-p-terphenyl group, or a 1-naphthyl group or a 2-naphthyl group, further preferably a phenyl group, a 2-biphenyl group, a 3-biphenyl group, or a 4-biphenyl group, or a 1-naphthyl group or a 2-naphthyl group, and particularly preferably a phenyl group.

[0093] The substituted aryl group having 6 to 30 ring carbon atoms is, for example, tolyl, tert-butylphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl or spirobifluorenyl.

[0094] The above-mentioned substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms includes isomeric groups when present.

[0095] In the above-mentioned substituted or unsubstituted aralkyl group having 7 to 36 carbon atoms, the aryl part of the aralkyl group having 7 to 36 carbon atoms is selected from the above-mentioned aryl groups having 6 to 30 ring carbon atoms, preferably 6 to 25, and more preferably 6 to 18 ring carbon atoms, and the alkyl part is selected from the above-mentioned substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, preferably 1 to 18, and more preferably 1 to 8 carbon atoms. The aralkyl group having 7 to 36 carbon atoms is, for example, benzyl, phenethyl or phenylpropyl, and is preferably benzyl.

[0096] The above-mentioned substituted or unsubstituted aralkyl group having 7 to 36 carbon atoms includes isomeric groups when present.

[0097] In the above-mentioned substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, the alkyl moiety of the alkoxy group having 1 to 30 carbon atoms is selected from the above-mentioned substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, and more preferably 1 to 8 carbon atoms. The alkoxy group having 1 to 30 carbon atoms is, for example, tert-butoxy, propoxy, ethoxy, or methoxy, preferably ethoxy or methoxy, and more preferably methoxy.

[0098] The above-mentioned substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms includes isomeric groups when present.

[0099] In the above-mentioned substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, the aryl part of the aryloxy group having 6 to 30 ring carbon atoms is selected from the above-mentioned substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms, preferably 6 to 25, and more preferably 6 to 18. The aryloxy group having 6 to 30 ring carbon atoms is, for example, a terphenyloxy group, a biphenyloxy group, or a phenoxy group, preferably a biphenyloxy group or a phenoxy group, and more preferably a phenoxy group.

[0100] The above-mentioned substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms includes isomeric groups when it exists.

[0101] The substituents of the mono-, di- or tri-substituted silyl group are selected from the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, and more preferably 1 to 8 carbon atoms, and the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, preferably 6 to 25 ring carbon atoms, and more preferably 6 to 18 ring carbon atoms. Preferred is a tri-substituted silyl group, and more preferred are, for example, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, propyldimethylsilyl, isopropyldimethylsilyl, triphenylsilyl, phenyldimethylsilyl, tert-butyldiphenylsilyl, or tritolylsilyl.

[0102] The above-mentioned monosubstituted, disubstituted or trisubstituted silyl group includes isomeric groups when it exists.

[0103] In the above-mentioned substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, the haloalkyl group having 1 to 30 carbon atoms is a group obtained by replacing at least one hydrogen atom, preferably 1 to 7 hydrogen atoms, or all hydrogen atoms of the above-mentioned alkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, and more preferably 1 to 8 carbon atoms with a halogen atom. The halogen atom is selected from a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and is preferably a fluorine atom. The haloalkyl group is preferably a fluoroalkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, and more preferably 1 to 8 carbon atoms, more preferably a heptafluoropropyl group, a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, or a trifluoromethyl group, further preferably a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, or a trifluoromethyl group, and particularly preferably a trifluoromethyl group.

[0104] The above-mentioned substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms includes isomeric groups when present.

[0105] In the above-mentioned substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms, the haloalkyl moiety of the haloalkoxy group having 1 to 30 carbon atoms is selected from the above-mentioned haloalkyl groups having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, and more preferably 1 to 8 carbon atoms. The haloalkoxy group is preferably a fluoroalkoxy group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, and more preferably 1 to 8 carbon atoms, more preferably a heptafluoropropoxy group, a pentafluoroethoxy group, a 2,2,2-trifluoroethoxy group, or a trifluoromethoxy group, further preferably a pentafluoroethoxy group, a 2,2,2-trifluoroethoxy group, or a trifluoromethoxy group, and particularly preferably a trifluoromethoxy group.

[0106] The substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms includes isomeric groups when present.

[0107] In the above-mentioned substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, the heteroaryl group having 5 to 30 ring atoms contains 1 to 5, preferably 1 to 3, more preferably 1 to 2 ring heteroatoms. The ring heteroatoms are selected from nitrogen atoms, sulfur atoms and oxygen atoms, for example. The free connecting bonds of the heteroaryl group are present on the ring carbon atoms, or, if physically possible, on the ring nitrogen atoms.

[0108] The heteroaryl group having 5 to 30 ring atoms is exemplified by pyrrolyl, furanyl, thienyl, pyridyl, imidazopyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, indolyl, isoindolyl, indolizinyl, quinolizinyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, indazolyl, benzisoxazolyl, benzo isothiazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, xanthenyl, benzofuranyl, isobenzofuranyl, naphthobenzofuranyl, dibenzofuranyl, benzothienyl (the same below), isobenzothienyl (the same below), naphthtobenzothienyl (the same below), dibenzothienyl (the same below), or carbazolyl.

[0109] Preferred are benzofuranyl, isobenzofuranyl, naphthobenzofuranyl, dibenzofuranyl, benzothiophenyl, isobenzothiophenyl, naphthobenzothiophenyl, dibenzothiophenyl, and carbazolyl (9-carbazolyl, or 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, or 4-carbazolyl).

[0110] Examples of the substituted heteroaryl group having 5 to 30 ring atoms include 9-phenylcarbazolyl, 9-biphenylcarbazolyl, 9-phenylphenylcarbazolyl, 9-naphthylcarbazolyl, phenyldibenzofuranyl, and phenyldibenzothienyl (hereinafter the same).

[0111] The above-mentioned substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms includes isomeric groups when present.

[0112] Selected from R 1 ~R 6 and R which is not a single bond to *a 7 ~R 9The ring structure formed by the two adjacent rings and the two ring-forming carbon atoms to which they are bonded is, for example, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 ring carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms, a substituted or unsubstituted aromatic heterocycle having 5 to 18 ring atoms, or a substituted or unsubstituted aliphatic heterocycle having 5 to 18 ring atoms.

[0113] The aromatic hydrocarbon ring having 6 to 18 ring carbon atoms is exemplified by a benzene ring, a biphenylene ring, a naphthalene ring, an anthracene ring, a benzanthracene ring, a phenanthrene ring, a triphenylene ring, a phenanthene ring, a pyrene ring, A ring or a triphenylene ring, preferably a benzene ring or a naphthalene ring.

[0114] The aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms is, for example, a cyclopentene ring, a cyclopentadiene ring, a cyclohexene ring, a cyclohexadiene ring, or an aliphatic ring obtained by partially hydrogenating the aromatic hydrocarbon ring having 6 to 18 ring carbon atoms.

[0115] The above-mentioned aromatic heterocyclic ring having 5 to 18 ring atoms is, for example, a pyrrole ring, a furan ring, a thiophene ring, a pyridine ring, an imidazole ring, a pyrazole ring, an indole ring, an isoindole ring, a benzofuran ring, an isobenzofuran ring, a benzothiophene ring, a benzimidazole ring, an indazole ring, a dibenzofuran ring, a naphthiobenzofuran ring, a dibenzothiophene ring, a naphthiobenzothiophene ring, a carbazole ring, or a benzocarbazole ring.

[0116] The aliphatic heterocyclic ring having 5 to 18 ring atoms is, for example, an aliphatic heterocyclic ring obtained by partially hydrogenating the aromatic heterocyclic ring having 5 to 18 ring atoms.

[0117] In one embodiment of the present invention, R 1 ~R 6 and R which is not a single bond to *a 7 ~R 9 Both are preferably hydrogen atoms.

[0118] R 11 ~R 18Each is independently a hydrogen atom or a substituent selected from a halogen atom; a cyano group; a nitro group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, and more preferably 1 to 8 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, preferably 3 to 10 ring carbon atoms, more preferably 3 to 8 ring carbon atoms, and more preferably 5 or 6 ring carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, preferably 6 to 25 ring carbon atoms, and more preferably 6 to 18 ring carbon atoms; a substituted or unsubstituted aralkyl group having 7 to 36 ring carbon atoms, preferably 7 to 26 ring carbon atoms, and more preferably 7 to 20 ring carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 30 ring carbon atoms, preferably 1 to 18 ring carbon atoms, and more preferably 1 to 8 ring carbon atoms; a substituted or unsubstituted cycloalkyl group having 6 to 30 ring carbon atoms, preferably 3 to 10 ring carbon atoms, and more preferably 3 to 8 ring carbon atoms; The group consisting of: a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, and more preferably 6 to 18 carbon atoms; a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, and more preferably 6 to 18 carbon atoms in the ring; a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, and more preferably 1 to 8 carbon atoms; a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, and more preferably 1 to 8 carbon atoms; and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, preferably 5 to 24 ring atoms, and more preferably 5 to 13 ring atoms.

[0119] Among them, selected from R 11 ~R 18 In the formula, the adjacent two independently represent a hydrogen atom or the above-mentioned substituent, or the adjacent two are bonded to each other to form a ring structure. That is, the adjacent two do not form a ring structure but independently represent a hydrogen atom or the above-mentioned substituent, or are bonded to each other to form a ring structure.

[0120] That is, R 11 ~R 18 Each independently represents a hydrogen atom or a substituent, or is selected from R 11 ~R 18 Adjacent groups are bonded to form a ring structure.

[0121] R 11 ~R 18The substituent represented by is preferably selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; more preferably selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.

[0122] R 11 ~R 18 The details of the substituents are the same as those described above for R 1 ~R 6 and R which is not a single bond to *a 7 ~R 9 The details of the corresponding substituents described are the same.

[0123] In one embodiment of the present invention, selected from R 11 ~R 18 Two adjacent ones of the group do not form a ring structure but each independently represents a hydrogen atom or the above-mentioned substituent. In another embodiment of the present invention, at least one group of adjacent two groups are bonded to each other to form a ring structure.

[0124] Selected from R 11 ~R 18 The details of the ring structure formed by the two adjacent carbon atoms in the ring and the two carbon atoms to which they are bonded are the same as those described above for R 1 ~R 6 and R which is not a single bond to *a 7 ~R 9 The details of the described ring structures are the same.

[0125] In one embodiment of the present invention, R 11 ~R 18 Both are preferably hydrogen atoms.

[0126] R 21 ~R 27Each is independently a hydrogen atom or a substituent selected from a halogen atom; a cyano group; a nitro group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, and more preferably 1 to 8 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, preferably 3 to 10 ring carbon atoms, more preferably 3 to 8 ring carbon atoms, and more preferably 5 or 6 ring carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, preferably 6 to 25 ring carbon atoms, and more preferably 6 to 18 ring carbon atoms; a substituted or unsubstituted aralkyl group having 7 to 36 ring carbon atoms, preferably 7 to 26 ring carbon atoms, and more preferably 7 to 20 ring carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 30 ring carbon atoms, preferably 1 to 18 ring carbon atoms, and more preferably 1 to 8 ring carbon atoms; a substituted or unsubstituted cycloalkyl group having 6 to 30 ring carbon atoms, preferably 3 to 10 ring carbon atoms, and more preferably 3 to 8 ring carbon atoms; The group consisting of: a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, and more preferably 6 to 18 carbon atoms; a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, and more preferably 6 to 18 carbon atoms in the ring; a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, and more preferably 1 to 8 carbon atoms; a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, and more preferably 1 to 8 carbon atoms; and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, preferably 5 to 24 ring atoms, and more preferably 5 to 13 ring atoms.

[0127] Among them, selected from R 21 ~R 27 In the formula, the adjacent two independently represent a hydrogen atom or the above-mentioned substituent, or the adjacent two are bonded to each other to form a ring structure. That is, the adjacent two do not form a ring structure but independently represent a hydrogen atom or the above-mentioned substituent, or are bonded to each other to form a ring structure.

[0128] That is, R 21 ~R 27 Each independently represents a hydrogen atom or a substituent, or is selected from R 21 ~R 27 Adjacent groups in the ring are bonded to form a ring structure.

[0129] R 21 ~R 27The substituent represented by is preferably selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; more preferably selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.

[0130] R 21 ~R 27 The details of the substituents are the same as those described above for R 1 ~R 6 and R which is not a single bond to *a 7 ~R 9 The details of the corresponding substituents described are the same.

[0131] In one embodiment of the present invention, selected from R 21 ~R 27 Two adjacent ones of the group do not form a ring structure but each independently represents a hydrogen atom or the above-mentioned substituent. In another embodiment of the present invention, at least one group of adjacent two groups are bonded to each other to form a ring structure.

[0132] Selected from R 21 ~R 27 The details of the ring structure formed by the two adjacent carbon atoms in the ring and the two carbon atoms to which they are bonded are the same as those described above for R 1 ~R 6 and R which is not a single bond to *a 7 ~R 9 The details of the described ring structures are the same.

[0133] In one embodiment of the present invention, R 21 ~R 27 Both are preferably hydrogen atoms.

[0134] Ar is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, preferably 6 to 25, and more preferably 6 to 18. Among the substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms, the aryl group having 6 to 30 ring carbon atoms is exemplified by phenyl, biphenyl, terphenyl, biphenylalkenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, triphenylenyl, phenanthren ... Benzo The invention further comprises a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, or a triphenylene group, and the phenyl group is preferably a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, and the phenyl group is further preferably a phenyl group, a biphenyl group, or a terphenyl group.

[0135] The biphenyl group is 2-biphenyl group, 3-biphenyl group or 4-biphenyl group, and 4-biphenyl group is particularly preferred.

[0136] The terphenyl group is 1,1':4',1"-terphenyl, 1,1':3',1"-terphenyl, or 1,1':2',1"-terphenyl, preferably 1,1':4',1"-terphenyl-2-yl, 1,1':4',1"-terphenyl-3-yl, 1,1':4',1"-terphenyl-4-yl, 1,1':3',1"-terphenyl-2-yl, 1,1':3',1"-terphenyl-3-yl, 1,1':4',1"-terphenyl-4-yl, Biphenyl-3-yl, 1,1':3',1"-terphenyl-4-yl, 1,1':2',1"-terphenyl-2-yl, 1,1':2',1"-terphenyl-3-yl, or 1,1':2',1"-terphenyl-4-yl, more preferably 1,1':4',1"-terphenyl-2-yl, 1,1':4',1"-terphenyl-3-yl, or 1,1':4',1"-terphenyl-4-yl.

[0137] The naphthyl group includes 1-naphthyl and 2-naphthyl.

[0138] The phenanthryl group is 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl or 9-phenanthryl, preferably 2-phenanthryl or 9-phenanthryl.

[0139] The triphenylene group is preferably 2-triphenylene group.

[0140] The substituted aryl group having 6 to 30 ring carbon atoms is, for example, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, or spirobifluorenyl.

[0141] The above-mentioned substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms includes isomeric groups when present.

[0142] L 1 is a single bond or L 11 , L 11 is a substituted or unsubstituted arylene group having 6 to 30, preferably 6 to 25, more preferably 6 to 18 ring carbon atoms. 1 Preferably, it is a single bond. In another embodiment, L 1 Preferably L 11 .

[0143] In L 11The substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms represented by the present invention is exemplified by phenylene, biphenylene, terphenylene, biphenylene, naphthylene, anthracenylene, benzanthrylene, phenanthrenylene, triphenylene, phenanthrenylene, py ... Benzoyl It is preferably a phenylene group, a biphenylene group, or a naphthylene group, more preferably a phenylene group, further preferably a 1,4-phenylene group, a 1,3-phenylene group, or a 1,2-phenylene group, and particularly preferably a 1,4-phenylene group.

[0144] The substituted arylene group having 6 to 30 ring carbon atoms is, for example, 9,9-dimethylfluorenylene, 9,9-diphenylfluorenylene, or spirobifluorenylene.

[0145] The above-mentioned substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms includes isomeric groups when present.

[0146] L 2 is a single bond or L 22 , L 22 is a substituted or unsubstituted arylene group having 6 to 30, preferably 6 to 25, more preferably 6 to 18 ring carbon atoms. 2 Preferably, it is a single bond. In another embodiment, L 2 Preferably L 22 .

[0147] In L 22 The substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms represented by the present invention is exemplified by phenylene, biphenylene, terphenylene, biphenylene, naphthylene, anthracenylene, benzanthrylene, phenanthrenylene, triphenylene, phenanthrenylene, py ... Benzoyl The group is preferably a phenylene group, a fluorenylene group, a fluoranthenylene group, a perylene group, or a triphenylene group, preferably a phenylene group, a biphenylene group, a naphthylene group, or a phenanthrylene group, more preferably a phenylene group or a biphenylene group, and further preferably a phenylene group.

[0148] The phenylene group is 1,2-phenylene, 1,3-phenylene or 1,4-phenylene, and 1,4-phenylene is particularly preferred.

[0149] The biphenylene is preferably 4,2'-biphenylene, 4,3'-biphenylene, or 4,4'-biphenylene, and particularly preferably 4,4'-biphenylene. 22In the case of 4,2'-biphenylene or 4,3'-biphenylene, it is preferred that the central nitrogen atom is bonded to the 4-position and the 4-dibenzofuranyl structure is bonded to the 2'-position or the 3'-position.

[0150] The naphthylene group is preferably a 1,4-naphthylene group or a 2,6-naphthylene group.

[0151] The phenanthryl group is preferably 2,7-phenanthryl group.

[0152] L 3 is a single bond or L 33 , L 33 is a substituted or unsubstituted arylene group having 6 to 30, preferably 6 to 25, more preferably 6 to 18 ring carbon atoms. 3 Preferably, it is a single bond. In another embodiment, L 3 Preferably L 33 .

[0153] In L 33 The substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms represented by the present invention is exemplified by phenylene, biphenylene, terphenylene, biphenylene, naphthylene, anthracenylene, benzanthrylene, phenanthrenylene, triphenylene, phenanthrenylene, py ... Benzoyl The phenylene group is preferably phenylene, and more preferably 1,4-phenylene.

[0154] In the present specification, the optional substituent group when expressed as "substituted or unsubstituted" is selected from the group consisting of a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, and more preferably 1 to 8 carbon atoms, a cycloalkyl group having 3 to 30 ring carbon atoms, preferably 3 to 10 ring carbon atoms, and more preferably 3 to 8 ring carbon atoms, and more preferably 5 or 6 ring carbon atoms, an aryl group having 6 to 30 ring carbon atoms, preferably 6 to 25 ring carbon atoms, and more preferably 6 to 18 ring carbon atoms, an aralkyl group having 7 to 36 ring carbon atoms, preferably 7 to 26 ring carbon atoms, and more preferably 7 to 20 ring carbon atoms, an alkoxy group having 1 to 30 ring carbon atoms, preferably 1 to 18 ring carbon atoms, and more preferably 1 to 8 ring carbon atoms. The group consisting of an aryloxy group having 6 to 30, preferably 6 to 25, more preferably 6 to 18 carbon atoms; a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from an alkyl group having 1 to 30, preferably 1 to 18, more preferably 1 to 8 carbon atoms and an aryl group having 6 to 30, preferably 6 to 25, more preferably 6 to 18 ring carbon atoms; a haloalkyl group having 1 to 30, preferably 1 to 18, more preferably 1 to 8 carbon atoms; a haloalkoxy group having 1 to 30, preferably 1 to 18, more preferably 1 to 8 carbon atoms; and a heteroaryl group having 5 to 30, preferably 5 to 24, more preferably 5 to 13 ring atoms.

[0155] The details of the optional substituents are the same as those described above for R 1 ~R 6 and R which is not a single bond to *a 7 ~R 9 The details of the corresponding substituents described are the same.

[0156] Specific examples of the compound (1) of the present invention are shown below, but the invention is not limited thereto.

[0157] [Chemistry 14]

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[0462]

[0463] The method for producing compound (1) is not particularly limited, and a person skilled in the art can easily produce it by the method described in the following examples or by a method modified by referring to a known synthesis method.

[0464] Materials for organic EL devices

[0465] The material for an organic EL element of the present invention contains compound (1). The content of compound (1) in the material for an organic EL element of the present invention is not particularly limited, and is, for example, 1% by mass or more (including 100%), preferably 10% by mass or more (including 100%), more preferably 50% by mass or more (including 100%), further preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%). The material for an organic EL element of the present invention is useful for manufacturing an organic EL element.

[0466] Organic EL elements

[0467] Next, the organic EL device of the present invention will be described.

[0468] The organic EL element comprises a cathode, an anode and an organic layer located between the cathode and the anode. The organic layer comprises a light-emitting layer, and at least one layer of the organic layer comprises the compound (1).

[0469] Examples of organic layers containing compound (1) include, but are not limited to, a hole transport region (hole injection layer, hole transport layer, electron blocking layer, exciton blocking layer, etc.) disposed between the anode and the light-emitting layer, a light-emitting layer, a spacer layer, an electron transport region (electron injection layer, electron transport layer, hole blocking layer, etc.) disposed between the cathode and the light-emitting layer. Compound (1) is preferably used as a material for the hole transport region or the light-emitting layer of a fluorescent or phosphorescent EL element, more preferably as a material for the hole transport region, and further preferably as a material for the hole transport layer, electron blocking layer, or exciton blocking layer.

[0470] The organic EL element of the present invention may be a single-color light-emitting element of a fluorescent or phosphorescent light-emitting type, or a white light-emitting element of a fluorescent / phosphorescent mixed type, or a simple type having a single light-emitting unit, or a series type having multiple light-emitting units, wherein a fluorescent light-emitting element is preferred. Here, "light-emitting unit" refers to the smallest unit that includes an organic layer, at least one of which is a light-emitting layer, and in which injected holes and electrons emit light by recombination.

[0471] For example, as a representative element structure of a simple organic EL element, the following element structures can be cited.

[0472] (1) Anode / light-emitting unit / cathode

[0473] In addition, the above-mentioned light-emitting unit may also be a stacked type having a plurality of phosphorescent light-emitting layers and fluorescent light-emitting layers. In this case, a spacer layer may be provided between each light-emitting layer for the purpose of preventing the excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer. The following shows a representative layer structure of a simplified light-emitting unit. The layers in parentheses are optional.

[0474] (a) (hole injection layer / ) hole transport layer / fluorescent light emitting layer ( / electron transport layer / electron injection layer)

[0475] (b) (hole injection layer / hole transport layer / phosphorescent light emitting layer / electron transport layer / electron injection layer)

[0476] (c) (hole injection layer / hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer ( / electron transport layer / electron injection layer)

[0477] (d) (hole injection layer / hole transport layer / first phosphorescent light-emitting layer / second phosphorescent light-emitting layer ( / electron transport layer / electron injection layer)

[0478] (e) (hole injection layer / ) hole transport layer / phosphorescent light emitting layer / spacer layer / fluorescent light emitting layer ( / electron transport layer / electron injection layer)

[0479] (f) (hole injection layer / hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer / spacer layer / fluorescent light emitting layer ( / electron transport layer / electron injection layer)

[0480] (g) (hole injection layer / hole transport layer / first phosphorescent emitting layer / spacer layer / second phosphorescent emitting layer / spacer layer / fluorescent emitting layer ( / electron transport layer / electron injection layer)

[0481] (h) (hole injection layer / ) hole transport layer / phosphorescent emitting layer / spacer layer / first fluorescent emitting layer / second fluorescent emitting layer ( / electron transport layer / electron injection layer)

[0482] (i) (hole injection layer / ) hole transport layer / electron blocking layer / fluorescent light emitting layer ( / electron transport layer / electron injection layer)

[0483] (j) (hole injection layer / ) hole transport layer / electron blocking layer / phosphorescent light emitting layer ( / electron transport layer / electron injection layer)

[0484] (k) (hole injection layer / ) hole transport layer / exciton blocking layer / fluorescent light emitting layer ( / electron transport layer / electron injection layer)

[0485] (l) (hole injection layer / hole transport layer / exciton blocking layer / phosphorescent light emitting layer ( / electron transport layer / electron injection layer)

[0486] (m) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent light emitting layer ( / electron transport layer / electron injection layer)

[0487] (n) (hole injection layer / ) first hole transport layer / second hole transport layer / phosphorescent light emitting layer ( / electron transport layer / electron injection layer)

[0488] (o) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent light emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer)

[0489] (p) (hole injection layer / ) first hole transport layer / second hole transport layer / phosphorescent light emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer)

[0490] (q) (hole injection layer / ) hole transport layer / fluorescent light emitting layer / hole blocking layer ( / electron transport layer / electron injection layer)

[0491] (r) (hole injection layer / ) hole transport layer / phosphorescent light emitting layer / hole blocking layer ( / electron transport layer / electron injection layer)

[0492] (s) (hole injection layer / ) hole transport layer / fluorescent light emitting layer / exciton blocking layer ( / electron transport layer / electron injection layer)

[0493] (t) (hole injection layer / ) hole transport layer / phosphorescent light emitting layer / exciton blocking layer ( / electron transport layer / electron injection layer)

[0494] Each of the above-mentioned phosphorescent or fluorescent light-emitting layers can be a layer showing a different light color from each other. Specifically, in the above-mentioned stacked light-emitting unit (f), a layer structure such as (hole injection layer / ) hole transport layer / first phosphorescent light-emitting layer (red light emission) / second phosphorescent light-emitting layer (green light emission) / spacer layer / fluorescent light-emitting layer (blue light emission) / electron transport layer can be cited.

[0495] It should be noted that an electron blocking layer may be appropriately provided between each light-emitting layer and the hole transport layer or the spacer layer. In addition, a hole blocking layer may be appropriately provided between each light-emitting layer and the electron transport layer. By providing an electron blocking layer or a hole blocking layer, electrons or holes may be enclosed in the light-emitting layer, thereby increasing the recombination probability of the charges in the light-emitting layer, thereby improving the luminous efficiency.

[0496] As a typical element structure of a tandem organic EL element, the following element structures can be cited.

[0497] (2) Anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode

[0498] Here, the first light-emitting unit and the second light-emitting unit may be independently selected from the light-emitting units described above, for example.

[0499] The intermediate layer is generally also called an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, or an intermediate insulating layer. It is a layer that supplies electrons to the first light-emitting unit and holes to the second light-emitting unit and can be formed using known materials.

[0500] Figure 1 : is a schematic diagram showing an example of the structure of the organic EL element of the present invention. The organic EL element 1 has a substrate 2, an anode 3, a cathode 4 and a light-emitting unit 10 arranged between the anode 3 and the cathode 4. The light-emitting unit 10 has a light-emitting layer 5. There is a hole transport region 6 (hole injection layer, hole transport layer, etc.) between the light-emitting layer 5 and the anode 3, and there is an electron transport region 7 (electron injection layer, electron transport layer, etc.) between the light-emitting layer 5 and the cathode 4. In addition, an electron blocking layer (not shown) may be provided on the anode 3 side of the light-emitting layer 5, and a hole blocking layer (not shown) may be provided on the cathode 4 side of the light-emitting layer 5, respectively. As a result, electrons and holes can be confined in the light-emitting layer 5, thereby further improving the generation efficiency of excitons in the light-emitting layer 5.

[0501] Figure 2 Schematic diagram showing another structure of the organic EL element of the present invention. The organic EL element 11 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 20 disposed between the anode 3 and the cathode 4. The light-emitting unit 20 has a light-emitting layer 5. The hole transport region disposed between the anode 3 and the light-emitting layer 5 is formed by a first hole transport layer 6a and a second hole transport layer 6b. In addition, the electron transport region disposed between the light-emitting layer 5 and the cathode 4 is formed by a first electron transport layer 7a and a second electron transport layer 7b.

[0502] It should be noted that in the present invention, a host combined with a fluorescent dopant (fluorescent luminescent material) is referred to as a fluorescent host, and a host combined with a phosphorescent dopant is referred to as a phosphorescent host. The fluorescent host and the phosphorescent host are not distinguished only by the molecular structure. That is, the phosphorescent host refers to a material that forms a phosphorescent luminescent layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material for forming a fluorescent luminescent layer. The same is true for the fluorescent host.

[0503] substrate

[0504] The substrate is used as a support of the organic EL element. As the substrate, for example, a plate of glass, quartz, plastic, etc. can be used. In addition, a flexible substrate can also be used. As the flexible substrate, for example, a plastic substrate formed of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, etc. can be cited. In addition, an inorganic vapor-deposited film can also be used.

[0505] anode

[0506] The anode formed on the substrate preferably uses a metal, alloy, conductive compound, and a mixture thereof with a large work function (for example, 4.0 eV or more). Specifically, for example, indium oxide-tin oxide (ITO: IndiumTinOxide, indium tin oxide); indium oxide-tin oxide containing silicon or silicon oxide; indium oxide-zinc oxide; indium oxide containing tungsten oxide and zinc oxide; graphene, etc. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the above metals (for example, titanium nitride) can be mentioned.

[0507] These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering a target containing 1 to 10 wt% zinc oxide relative to indium oxide; indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering a target containing 0.5 to 5 wt% tungsten oxide and 0.1 to 1 wt% zinc oxide relative to indium oxide. In addition, it can also be produced by vacuum evaporation, coating, inkjet, spin coating, etc.

[0508] The hole injection layer formed adjacent to the anode is formed using a material that easily allows hole injection regardless of the work function of the anode. Therefore, generally used materials (such as metals, alloys, conductive compounds, and mixtures thereof, elements belonging to the first or second group of the periodic table) can be used as electrode materials.

[0509] It is also possible to use elements belonging to the first or second group of the periodic table as materials with a small work function, i.e., alkali metals such as lithium (Li), cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing them. It should be noted that when using alkali metals, alkaline earth metals, and alloys containing them to form anodes, vacuum evaporation methods and sputtering methods can be used. In addition, when using silver paste, coating methods, inkjet methods, etc. can be used.

[0510] Hole injection layer

[0511] The hole injection layer is a layer containing a material with high hole injection properties (hole injection material). The compound (1) can be used in the hole injection layer alone or in combination with the following materials.

[0512] As hole injecting materials other than compound (1), molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide and the like can be used.

[0513] Examples of hole injection layer materials include low molecular weight organic compounds such as 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), and 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DPAB). NTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) and other aromatic amine compounds.

[0514] High molecular weight compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, there can be mentioned high molecular weight compounds such as poly(N-vinylcarbazole) (abbreviated as: PVK), poly(4-vinyltriphenylamine) (abbreviated as: PVTPA), poly[N-(4-(N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated as: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated as: Poly-TPD). In addition, high molecular weight compounds to which an acid is added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

[0515] It is also preferable to use an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K) in combination with the compound (1).

[0516] [Chemistry 167]

[0517]

[0518] (In the above formula, R 21 ~R 26Each independently represents a cyano group, -CONH 2 , carboxyl, or -COOR 27 (R 27 represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms). In addition, R 21 and R 22 , R 23 and R 24 , and R 25 and R 26 Two adjacent groups can bond to each other to form a group represented by -CO-O-CO-. )

[0519] As R 27 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl and the like can be mentioned.

[0520] Hole transport layer

[0521] The hole transport layer is a layer containing a material having a high hole transport property (hole transport material). It is preferred to use the compound (1) alone or in combination with the following compounds for the hole transport layer.

[0522] As hole-transporting materials other than the compound (1), for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used.

[0523] Examples of the aromatic amine compound include: 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated as BAFLP), 4,4'-bis[N-(9,9-dimethylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), The above compounds have 10 -6 cm 2 / Vs and above hole mobility.

[0524] Examples of the carbazole derivative include 4,4′-di(9-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: PCzPA).

[0525] Examples of the anthracene derivative include 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and 9,10-diphenylanthracene (abbreviation: DPAnth).

[0526] A polymer compound such as poly(N-vinylcarbazole) (abbreviation: PVK) or poly(4-vinyltriphenylamine) (abbreviation: PVTPA) may also be used.

[0527] In addition, as long as the hole-transporting property is higher than the electron-transporting property, a compound other than the above-mentioned compounds may be used.

[0528] The hole transport layer may be a single-layer structure or a multilayer structure including more than two layers. For example, the hole transport layer may be a two-layer structure including a first hole transport layer (anode side) and a second hole transport layer (cathode side). In one embodiment of the present invention, the hole transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, or the hole transport layer closest to the light-emitting layer in the multilayer structure, such as the second hole transport layer, is preferably adjacent to the light-emitting layer. In another embodiment of the present invention, a blocking layer described later may be sandwiched between the hole transport layer and the light-emitting layer of the single-layer structure, or between the hole transport layer and the light-emitting layer closest to the light-emitting layer in the multilayer structure.

[0529] In the above-mentioned two-layer hole transport layer structure, compound (1) may be contained in one of the first hole transport layer and the second hole transport layer, or may be contained in both. It should be noted that the compound (1) contained in the first hole transport layer is different from the compound (1) contained in the second hole transport layer.

[0530] In one embodiment of the present invention, it is preferred that compound (1) is contained in the first hole transport layer. In another embodiment, it is preferred that compound (1) is contained in the second hole transport layer. In still another embodiment, it is preferred that compound (1) is contained in both the first hole transport layer and the second hole transport layer.

[0531] Dopant materials for the light-emitting layer

[0532] The light-emitting layer is a layer containing a material with high luminescence (dopant material), and various materials can be used. For example, fluorescent materials and phosphorescent materials can be used as dopant materials. Fluorescent materials are compounds that emit light in a singlet excited state, and phosphorescent materials are compounds that emit light in a triplet excited state.

[0533] As the blue fluorescent material that can be used for the light-emitting layer, pyrene derivatives, styrylamine derivatives, Derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. Specifically, N, N'-bis [4- (9H-carbazole-9-yl) phenyl] -N, N'-diphenylstilbene-4, 4'-diamine (abbreviation: YGA2S), 4- (9H-carbazole-9-yl) -4'- (10-phenyl-9-anthracenyl) triphenylamine (abbreviation: YGAPA), 4- (10-phenyl-9-anthracenyl) -4'- (9-phenyl-9H-carbazole-3-yl) triphenylamine (abbreviation: PCBAPA), etc. can be mentioned.

[0534] As green fluorescent light-emitting materials that can be used for the light-emitting layer, aromatic amine derivatives can be used. Specifically, N-(9,10-diphenyl-2-anthracenyl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthracenyl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCABPhA), N-(9,10-diphenyl-2-anthracenyl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPAPhA), PA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthracenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviated as 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviated as DPhAPhA), etc.

[0535] As the red fluorescent luminescent material that can be used for the light-emitting layer, there can be used tetracene derivatives, diamine derivatives, etc. Specifically, there can be mentioned N, N, N', N'-tetrakis (4-methylphenyl) tetracene-5, 11-diamine (abbreviation: p-mPhTD), 7, 14-diphenyl-N, N, N', N'-tetrakis (4-methylphenyl) acenaphtho[1, 2-a] fluoranthene-3, 10-diamine (abbreviation: p-mPhAFD), etc.

[0536] As a blue phosphorescent material that can be used for the light-emitting layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used. Specifically, bis[2-(4',6'-difluorophenyl)pyridine-N, C2']iridium(III)tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridine-N, C2']iridium(III)picolinate (abbreviation: FIrpic), bis[2-(3',5'-bis(trifluoromethyl)phenyl)pyridine-N, C2']iridium(III)picolinate (abbreviation: Ir(CF3ppy)2(pic)), bis[2-(4',6'-difluorophenyl)pyridine-N, C2']iridium(III)acetylacetonate (abbreviation: FIracac), etc. can be cited.

[0537] As green phosphorescent materials that can be used for the light-emitting layer, iridium complexes are used, such as tris(2-phenylpyridine-N, C2')iridium(III) (abbreviated as Ir(ppy)3), bis(2-phenylpyridine-N, C2')iridium(III)acetylacetonate (abbreviated as Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazole)iridium(III)acetylacetonate (abbreviated as Ir(pbi)2(acac)), and bis(benzo[h]quinoline)iridium(III)acetylacetonate (abbreviated as Ir(bzq)2(acac)).

[0538] As a red phosphorescent material that can be used for the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used. Specifically, organic metal complexes such as bis[2-(2'-benzo[4,5-α]thienyl)pyridine-N,C3']iridium(III)acetylacetonate (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinoline-N,C2')iridium(III)acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxaline]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrinplatinum(II) (abbreviation: PtOEP) can be cited.

[0539] In addition, rare earth metal complexes such as tris(acetylacetonate)(monophenanthroline)terbium(III) (abbreviated as: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedione)(monophenanthroline)europium(III) (abbreviated as: Eu(DBM)3(Phen)), and tris[1-(2-thiophenoyl)-3,3,3-trifluoroacetone](monophenanthroline)europium(III) (abbreviated as: Eu(TTA)3(Phen)) can be used as phosphorescent materials because the luminescence comes from rare earth metal ions (electron transitions between different multiplicities).

[0540] Host material of the light-emitting layer

[0541] The light-emitting layer may be formed by dispersing the above-mentioned dopant material in other materials (host materials). Compound (1) may be used as the host material, and various materials may be used in addition. It is preferred to use a material having a lower lowest unoccupied molecular orbital energy level (LUMO energy level) than the dopant material and a lower highest occupied molecular orbital energy level (HOMO energy level) than the dopant material.

[0542] As a host material other than compound (1), for example,

[0543] (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes,

[0544] (2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives,

[0545] (3) Carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or Derivatives and other condensed aromatic compounds,

[0546] (4) Aromatic amine compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives.

[0547] For example, metal complexes that can be used include tris(8-hydroxyquinoline)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-hydroxyquinoline)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviation: BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviation: ZnBTZ);

[0548] 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2',2"-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP) and other heterocyclic compounds;

[0549] 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviated as DPPA), 9,10-di(2-naphthyl)anthracene (abbreviated as DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviated as : t-BuDNA), 9,9'-bianthracene (abbreviated as: BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviated as: DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviated as: DPNS2), 3,3',3"-(benzene-1,3,5-triyl)tripyrene (abbreviated as: TPB3), 9,10-diphenylanthracene (abbreviated as: DPAnth), 6,12-dimethoxy-5,11-diphenyl Etc. fused aromatic compounds; and

[0550] N,N-diphenyl-9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole-3-amine (abbreviation: CzAlPA), 4-(10-phenyl-9-anthracenyl)triphenylamine (abbreviation: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthracenyl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthracenyl)-N,9-diphenyl- Aromatic amine compounds such as 9H-carbazole-3-amine (abbreviation: 2PCAPA), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), and 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). Two or more types of the host material may be used.

[0551] In particular, in the case of a blue fluorescent element, it is preferable to use the following anthracene compound as a host material.

[0552] [Chemistry 168]

[0553]

[0554] [Chemistry 169]

[0555]

[0556] [Chemistry 170]

[0557]

[0558] Electron transport layer

[0559] The electron transport layer is a layer containing a material with high electron transport properties (electron transport material). For example, the following can be used in the electron transport layer:

[0560] (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes,

[0561] (2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives,

[0562] (3)Polymer compounds.

[0563] Examples of the metal complex include tris(8-hydroxyquinoline)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-hydroxyquinoline)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium (abbreviation: BeBq 2 ), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviation: BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviation: ZnBTZ).

[0564] Examples of the heteroaromatic compound include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), and 4,4′-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs).

[0565] Examples of the polymer compound include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).

[0566] The above materials are 10 -6 cm 2 It should be noted that materials other than the above may be used for the electron transport layer as long as the electron transport property is higher than the hole transport property.

[0567] The electron transport layer may be a single layer or a multilayer including two or more layers. For example, the electron transport layer may be a layer including a first electron transport layer (anode side) and a second electron transport layer (cathode side). The two or more electron transport layers are each formed by the above-mentioned electron transport material.

[0568] Electron injection layer

[0569] The electron injection layer is a layer containing a material with high electron injection properties. The electron injection layer can be made of lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), alkali metals, alkaline earth metals, or compounds thereof such as lithium oxide (LiOx). In addition, materials obtained by making materials having electron transport properties contain alkali metals, alkaline earth metals, or compounds thereof, specifically materials obtained by making Alq contain magnesium (Mg), etc. It should be noted that, at this time, electron injection from the cathode can be performed more efficiently.

[0570] Alternatively, a composite material formed by mixing an organic compound and an electron donor (donor) can also be used for the electron injection layer. Since the organic compound accepts electrons from the electron donor, the electron injection and electron transport properties of such a composite material are excellent. At this time, as an organic compound, it is preferably a material with excellent transmission of the accepted electrons. Specifically, for example, the above-mentioned materials (metal complexes, heteroaromatic compounds, etc.) constituting the electron transport layer can be used. As an electron donor, any material that exhibits electron donation properties to the organic compound can be used. Specifically, alkali metals, alkaline earth metals and rare earth metals are preferred, and lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. can be cited. In addition, alkali metal oxides and alkaline earth metal oxides are preferred, and lithium oxide, calcium oxide, barium oxide, etc. can be cited. In addition, Lewis bases such as magnesium oxide can also be used. In addition, organic compounds such as tetrathiafulvalene (abbreviated as: TTF) can also be used.

[0571] cathode

[0572] The cathode preferably utilizes metals, alloys, conductive compounds, and mixtures thereof with a small work function (specifically, less than 3.8 eV). Specific examples of such cathode materials include elements belonging to the first or second group of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys thereof (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), and ytterbium (Yb), and alloys thereof.

[0573] It should be noted that when an alkali metal, an alkaline earth metal, or an alloy thereof is used to form the cathode, a vacuum deposition method or a sputtering method may be used. In addition, when a silver paste or the like is used, a coating method or an inkjet method may be used.

[0574] It should be noted that, by providing an electron injection layer, a cathode can be formed using various conductive materials such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, regardless of the size of the work function. These conductive materials can be formed into films using sputtering, inkjet, spin coating, etc.

[0575] Insulation layer

[0576] Organic EL elements are prone to pixel defects due to leakage and short circuits due to the application of an electric field to an ultra-thin film. In order to prevent such pixel defects, an insulating layer including an insulating thin film layer may be inserted between a pair of electrodes.

[0577] Examples of the material used in the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, and vanadium oxide. It should be noted that mixtures and laminates thereof may be used.

[0578] Spacer

[0579] The above-mentioned spacer layer refers to a layer provided between the fluorescent emitting layer and the phosphorescent emitting layer, for example, in order to prevent the excitons generated in the phosphorescent emitting layer from diffusing to the fluorescent emitting layer or to adjust the carrier balance when the fluorescent emitting layer and the phosphorescent emitting layer are stacked. In addition, the spacer layer may also be provided between a plurality of phosphorescent emitting layers.

[0580] Since the spacer layer is disposed between the light-emitting layers, it is preferably a material having both electron transport and hole transport properties. In addition, in order to prevent the diffusion of triplet energy in the adjacent phosphorescent light-emitting layer, the triplet energy is preferably above 2.6 eV. As the material for the spacer layer, the same material as the material for the hole transport layer mentioned above can be cited.

[0581] Barrier layer

[0582] Blocking layers such as an electron blocking layer, a hole blocking layer, and an exciton blocking layer may be provided adjacent to the light-emitting layer. The electron blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole transport layer, and the hole blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron transport layer. The exciton blocking layer has the function of preventing excitons generated in the light-emitting layer from diffusing to surrounding layers and confining the excitons in the light-emitting layer.

[0583] Each layer of the organic EL element can be formed by a conventionally known vapor deposition method, coating method, etc. For example, it can be formed by a known method based on a vapor deposition method such as a vacuum vapor deposition method, a molecular beam vapor deposition method (MBE method), or a coating method such as a dip coating method, a spin coating method, a casting method, a rod coating method, a roll coating method, etc. using a solution of a compound forming a layer.

[0584] The thickness of each layer is not particularly limited. Generally, if the thickness is too thin, defects such as pinholes are likely to occur, whereas if it is too thick, a high driving voltage is required and the efficiency deteriorates. Therefore, it is usually 5 nm to 10 μm, and more preferably 10 nm to 0.2 μm.

[0585] The organic EL element can be used in electronic devices such as display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and light-emitting devices for lighting and vehicle lamps.

[0586] Example

[0587] Hereinafter, the present invention will be described in further detail using examples, but the present invention is not limited to the following examples.

[0588] Intermediate Synthesis Example A Synthesis of Intermediate A

[0589] [Chemistry 171]

[0590]

[0591] (A-1) Synthesis of Intermediate A-1

[0592] 1-Bromo-2-fluorobenzene (7.80 mL, 71.8 mmol) was added to a solution of carbazole (10 g, 59.8 mmol) and cesium carbonate (39.0 g, 120 mmol) in N-methylpyrrolidone (NMP, 59.8 mL), and heated and stirred at 160 ° C for 16 hours. The reaction solution was cooled to room temperature, toluene was added, and the insoluble matter was filtered out. The obtained solution was washed with water, dried over anhydrous sodium sulfate, and refined by silica gel column chromatography. The obtained residue was crystallized to obtain intermediate A-1 (18.3 g). The yield was 94%.

[0593] (A-2) Synthesis of Intermediate A-2

[0594] Under an argon atmosphere, a tetrahydrofuran (THF, 124 mL) solution of intermediate A-1 (8.0 g, 24.8 mmol) was cooled with a dry ice / acetone bath. A 1.6 M n-butyl lithium hexane solution (17.1 mL, 27.3 mmol) was added dropwise to the cooled solution and stirred for 2 hours. A THF (10 mL) solution of trimethyl borate (3.33 mL, 29.8 mmol) was added dropwise and stirred for 1 hour, then the dry ice / acetone bath was removed and the temperature was raised to room temperature. The reaction solution was cooled with an ice-water bath, 2 M hydrochloric acid was added, the temperature was raised to room temperature, and stirred for 1 hour. The obtained reaction solution was extracted with ethyl acetate, the organic layer was washed with water, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was crystallized to obtain intermediate A-2 (4.91 g). The yield was 69%.

[0595] (A-3) Synthesis of Intermediate A

[0596] Under argon atmosphere, a solution of intermediate A-2 (4.16 g, 14.5 mmol), 1-bromo-4-iodobenzene (4.92 g, 17.4 mmol), tetrakis(triphenylphosphine)palladium(0) (0.324 g, 0.28 mmol) and sodium carbonate (3.07 g, 29 mmol) in ethylene glycol dimethyl ether (DME, 40 mL) / water (7 mL) was stirred at 78 ° C for 18 hours. After cooling to room temperature, methanol was added and the refined solid was filtered out. The obtained solid was purified by silica gel column chromatography and recrystallization to obtain intermediate A (3.98 g). The yield was 69%.

[0597] Synthesis Example 1 Synthesis of Compound 1

[0598] [Chemistry 172]

[0599]

[0600] Under argon atmosphere, a mixture of intermediate A (3.18 g, 8.0 mmol), intermediate B (3.29 g, 8.0 mmol) synthesized by the same method as described in WO2007 / 125714, palladium acetate (II) (0.036 g, 0.16 mmol), tri-tert-butylphosphine (0.065 g, 0.32 mmol), sodium tert-butoxide (0.93 g, 9.6 mmol) and xylene (50 mL) was stirred at 125 ° C for 2.5 hours. The reaction solution was cooled to room temperature, methanol was added and stirred, and the precipitated solid was filtered out. The obtained solid was refined by silica gel column chromatography and recrystallization to obtain a white solid (3.14 g). The yield was 54%.

[0601] The obtained compound was identified as Compound 1 by mass spectrometry analysis (molecular weight: 728.28, m / e=728).

[0602] Synthesis Example 2 Synthesis of Compound 2

[0603] [Chemistry 173]

[0604]

[0605] The same operation as in Synthesis Example 1 was carried out except that Intermediate C synthesized in the same manner as the method described in WO2010 / 061824 was used instead of Intermediate B.

[0606] The obtained compound was identified as Compound 2 by mass spectrometry analysis (m / e=804, relative molecular weight: 804.31).

[0607] Intermediate Synthesis Example D Synthesis of Intermediate D

[0608] [Chemistry 174]

[0609]

[0610] Under argon atmosphere, a mixture of 4-bromoaniline (23.7 g, 138 mmol), dibenzofuran-4-ylboronic acid (boronicacid) (29.2 g, 138 mmol), tetrakis(triphenylphosphine)palladium (0) (3.18 g, 2.75 mmol), 2M sodium carbonate aqueous solution (138 mL), toluene (300 mL) and ethanol (100 mL) was stirred at 70°C for 2 hours. After returning to room temperature, the reaction solution was extracted with toluene. The toluene layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain intermediate D (20.9 g). The yield was 58%.

[0611] Synthesis Example 3 Synthesis of Compound 3

[0612] [Chemistry 175]

[0613]

[0614] (3-1) Synthesis of Intermediate E

[0615] Under an argon atmosphere, a xylene (35 mL) solution of intermediate D (2.09 g, 8.06 mmol) and 3-bromobiphenyl (1.45 g, 6.2 mmol) was heated to 85°C. After adding tris(dibenzylideneacetone)dipalladium(0) (85.2 mg, 0.093 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) (116 mg, 0.186 mmol) and sodium tert-butoxide (1.19 g, 12.4 mmol), the temperature was raised to 105°C and the mixture was stirred for 16 hours. After returning to room temperature, water was added to the reaction solution and the liquid was separated. After the organic layer was concentrated under reduced pressure, the residue was purified by column chromatography to obtain intermediate E (1.66 g). The yield was 65%.

[0616] (3-2) Synthesis of Compound 3

[0617] Except that Intermediate E was used instead of Intermediate B, the same operation as in Synthesis Example 1 was carried out.

[0618] The obtained compound was identified as Compound 3 by mass spectrometry analysis (molecular weight: 728.28, m / e=728).

[0619] Synthesis Example 4 Synthesis of Compound 4

[0620] [Chemistry 176]

[0621]

[0622] (4-1) Synthesis of Intermediate F

[0623] Intermediate F was obtained by carrying out the same operation as in (3-1) of Synthesis Example 3 except that 2-bromobiphenyl was used instead of 3-bromobiphenyl.

[0624] (4-2) Synthesis of Compound 4

[0625] Except that Intermediate F was used instead of Intermediate B, the same operation as in Synthesis Example 1 was carried out.

[0626] The obtained compound was identified as Compound 4 by mass spectrometry analysis (molecular weight: 728.28, m / e=728).

[0627] Synthesis Example 5 Synthesis of Compound 5

[0628] [Chemistry 177]

[0629]

[0630] (5-1) Synthesis of intermediate G

[0631] Intermediate G was obtained by carrying out the same operation as in (3-1) of Synthesis Example 3 except that 1-bromonaphthalene was used instead of 3-bromobiphenyl.

[0632] (5-2) Synthesis of Compound 5

[0633] Except that Intermediate G was used instead of Intermediate B, the same operation as in Synthesis Example 1 was carried out.

[0634] The obtained compound was identified as Compound 5 by mass spectrometry analysis (m / e=702, relative molecular weight: 702.27).

[0635] Synthesis Example 6 Synthesis of Compound 6

[0636] [Chemistry 178]

[0637]

[0638] (6-1) Synthesis of intermediate H

[0639] Intermediate H was obtained by carrying out the same operation as in (3-1) of Synthesis Example 3 except that 1-(4-bromophenyl)naphthalene was used instead of 3-bromobiphenyl.

[0640] (6-2) Synthesis of Compound 6

[0641] Except that Intermediate H was used instead of Intermediate B, the same operation as in Synthesis Example 1 was carried out.

[0642] The obtained compound was identified as Compound 6 by mass spectrometry analysis (m / e=778, relative molecular weight: 778.30).

[0643] Synthesis Example 7 Synthesis of Compound 7

[0644] [Chemistry 179]

[0645]

[0646] (7-1) Synthesis of Intermediate I

[0647] Under nitrogen atmosphere, a mixture of 2-iodophenanthrene (3.04 g, 10.0 mmol), 4-bromophenylboric acid (2.00 g, 10.0 mmol), tetrakis(triphenylphosphine)palladium (0) (0.231 g, 0.200 mmol), 2M sodium carbonate aqueous solution (60 mL, 120 mmol), 1,2-dimethoxyethane (DME) (50 mL) and water (60 mL) synthesized by the method described in WO2009 / 116628 was stirred at 80°C for 5 hours. After the reaction solution was cooled to room temperature, the precipitated crystals were filtered out, washed with hexane, then washed with water, and dried to obtain the target intermediate I (3.28 g). The yield was 99%.

[0648] (7-2) Synthesis of Intermediate J

[0649] Intermediate J was obtained by carrying out the same operation as in (3-1) of Synthesis Example 3 except that Intermediate I was used in place of 3-bromobiphenyl.

[0650] (7-3) Synthesis of Compound 7

[0651] The same operation as in Synthesis Example 1 was carried out except that Intermediate J synthesized in (7-2) was used instead of Intermediate B.

[0652] The obtained compound was identified as Compound 6 by mass spectrometry analysis (m / e=828, relative molecular weight 828.31).

[0653] Synthesis Example 8 Synthesis of Compound 8

[0654] [Chemistry 180]

[0655]

[0656] [Chemistry 181]

[0657]

[0658] (8-1) Synthesis of intermediate K

[0659] Under argon atmosphere, a mixture of intermediate A-2 (2.18 g, 7.59 mmol) synthesized in the same manner as (A-2) of intermediate synthesis example A, 1-bromo-3-chlorobenzene (1.60 g, 8.36 mmol), tetrakis(triphenylphosphine)palladium (0) (0.17 g, 0.147 mmol), 2M sodium carbonate aqueous solution (12 mL, 24 mmol), and 1,2-dimethoxyethane (DME) (40 mL) was refluxed for 7 hours. After the reaction solution was cooled to room temperature, water was added and extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain intermediate K (2.52 g). The yield was 94%.

[0660] (8-2) Synthesis of Intermediate L

[0661] Under argon atmosphere, a mixture of intermediate B (12.35 g, 30.0 mmol), 1-bromo-4-iodobenzene (8.49 g, 30.0 mmol), palladium (II) acetate (0.07 g, 0.313 mmol), Xantphos (0.17 g, 0.294 mmol), sodium tert-butoxide (4.32 g, 45.0 mmol) and toluene (150 mL) synthesized by the same operation as described in WO2007 / 125714 was stirred at 100 ° C for 23 hours. After the reaction solution was cooled to room temperature, water was added and extracted with ethyl acetate. The obtained organic layer was filtered through diatomaceous earth, and the filtrate was washed with water and saturated brine and dried over anhydrous magnesium sulfate. After filtering, the filtrate was concentrated under reduced pressure. The obtained residue was refined by silica gel column chromatography to obtain intermediate L (14.65 g). The yield was 86%.

[0662] (8-3) Synthesis of intermediate M

[0663] Under argon atmosphere, a THF (110 mL) solution of intermediate L (8.4 g, 14.83 mmol) was cooled with a dry ice / methanol bath, and a 1.5 M hexane solution (12 mL, 18.6 mmol) of n-butyl lithium was added dropwise, and stirred for 1 hour. Triisopropyl borate (11 mL, 47.7 mmol) was added dropwise to the reaction solution, stirred for 1 hour, and further stirred for 1.5 hours at room temperature. 1 M hydrochloric acid (20 mL) and water (110 mL) were added to the reaction solution and stirred for 30 minutes. The obtained reaction solution was separated and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried with anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was washed with ethyl acetate to obtain intermediate M (3.74 g). The yield was 48%.

[0664] (8-4) Synthesis of Compound 8

[0665] Under argon atmosphere, intermediate M (2.33 g, 4.38 mmol), intermediate K (1.55 g, 4.38 mmol), PdCl 2 (Amphos) 2 A mixture of (0.06 g, 0.085 mmol), 1,2-dimethoxyethane (DME) (37 mL) and 2M sodium carbonate aqueous solution (7 mL, 14 mmol) was refluxed for 5 hours. The reaction solution was cooled to room temperature, the precipitated solid was filtered out, and washed with DME and water. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (1.60 g). The yield was 45%.

[0666] The obtained compound was identified as Compound 8 by mass spectrometry analysis (m / e=804, relative molecular weight 804.31).

[0667] Example 1

[0668] Manufacturing of organic EL elements

[0669] A 25 mm×75 mm×1.1 mm glass substrate with an ITO transparent electrode (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The thickness of the ITO transparent electrode was 130 nm.

[0670] The washed glass substrate with the ITO transparent electrode was mounted on a substrate holder of a vacuum deposition apparatus, and first, the following compound (HI-1) was deposited to cover the ITO transparent electrode to form a hole injection layer with a thickness of 5 nm.

[0671] Next, the following compound HT-1 (first hole transport layer material) was deposited on the hole injection layer to form a first hole transport layer having a film thickness of 80 nm.

[0672] Next, Compound 1 (second hole transport layer material) synthesized in Synthesis Example 1 was deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 10 nm.

[0673] Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated on the second hole transport layer to form a 25 nm thick light emitting layer. The concentration of compound BD-1 in the light emitting layer was 4.0 mass %.

[0674] Next, the following compound ET-1 was deposited on the light-emitting layer to form a first electron transport layer having a film thickness of 10 nm.

[0675] Next, the following compound ET-2 was vapor-deposited on the first electron transport layer to form a second electron transport layer having a film thickness of 15 nm.

[0676] Next, LiF was vapor-deposited on the second electron transport layer to form an electron injecting electrode (cathode) having a film thickness of 1 nm.

[0677] Then, metal Al was vapor-deposited on the LiF film to form a metal Al cathode having a film thickness of 80 nm.

[0678] [Chemistry 182]

[0679]

[0680] [Chemistry 183]

[0681]

[0682] Determination of component life

[0683] The obtained organic EL device was heated at a current density of 50 mA / cm 2 The battery was driven by direct current, and the time until the luminance decreased to 95% of the initial luminance was measured, which was defined as the 95% life (LT95).

[0684] Embodiments 2 to 8

[0685] The same operation as in Example 1 was carried out except that Compounds 2 to 8 were used as the second hole transport layer material instead of Compound 1, respectively, to produce organic EL devices, and the 95% lifetime (LT95) was measured in the same manner as in Example 1. The results are shown in Table 1.

[0686] Comparative Examples 1 and 2

[0687] Each organic EL device was manufactured in the same manner as in Example 1 except that Comparative Compound 1 (the compound described in Patent Document 3) or Comparative Compound 2 (the compound described in Patent Document 4) was used as the second hole transport layer material instead of Compound 1, and the 95% lifetime (LT95) was measured in the same manner as in Example 1. The results are shown in Table 1.

[0688] [Table 1]

[0689] Table 1 Materials for the second hole transport layer LT95(h) Example 1 Compound 1 140 Example 2 Compound 2 140 Example 3 Compound 3 120 Example 4 Compound 4 130 Example 5 Compound 5 120 Example 6 Compound 6 140 Example 7 Compound 7 145 Example 8 Compound 8 145 Comparative Example 1 Comparative Compound 1 85 Comparative Example 2 Comparative Compound 2 90

[0690] [Chemistry 184]

[0691]

[0692] [Chemistry 185]

[0693]

[0694] Compounds 1 to 8 of the present invention satisfy the following two requirements, namely, structural requirement A: 4-dibenzofuranyl group and structural requirement B: biphenyl group having an N-carbazolyl group bonded to the ortho position of the terminal benzene ring.

[0695] Comparative compound 1 does not satisfy structural requirement A. Comparative compound 2 does not satisfy structural requirement B because the N-carbazolyl group is bonded to the meta position of the terminal benzene ring of the biphenyl group.

[0696] As can be seen from Table 1, the compounds 1 to 8 of the present invention satisfying both structural requirements A and B provide significantly improved device life compared to the comparative compounds 1 and 2 satisfying only one of the structural requirements A and B.

[0697] Explanation of symbols

[0698] 1.11 Organic EL elements

[0699] 2 substrate

[0700] 3 Anode

[0701] 4 Cathode

[0702] 5. Luminous layer

[0703] 6 Hole transport region (hole transport layer)

[0704] 6a 1st hole transport layer

[0705] 6b Second hole transport layer

[0706] 7 Electron transport region (electron transport layer)

[0707] 7a 1st electron transport layer

[0708] 7b Second electron transport layer

[0709] 10, 20 light units

Claims

1. A compound represented by the following formula (1), In formula (1), R 7 , R 8 and R 9 One of them is a single bond to *a; R 1 ~R 6 and R which is not a single bond to *a 7 ~R 9 are each independently a hydrogen atom or a substituent, the substituent being an unsubstituted phenyl group, in, Selected from R 1 ~R 6 and R which is not a single bond to *a 7 ~R 9 The two adjacent ones in are not bonded to each other and thus do not form a ring structure; R 11 ~R 18 are each independently a hydrogen atom or a substituent, the substituent being an unsubstituted phenyl group, Among them, selected from R 11 ~R 18 The two adjacent ones in do not form a ring structure; R 21 ~R 27 are each independently a hydrogen atom or a substituent, the substituent being an unsubstituted phenyl group, Among them, selected from R 21 ~R 27 The two adjacent ones in do not form a ring structure; Ar is an unsubstituted aryl group having 6 to 18 ring carbon atoms; L 1 is a single bond or L 11 , L 11 is a substituted or unsubstituted phenylene group; L 2 is a single bond or L 22 , L 22 is a substituted or unsubstituted phenylene group; L 3 is a single bond or L 33 , L 33 is a substituted or unsubstituted phenylene group, When expressed as "substituted or unsubstituted", the substituent is unsubstituted phenyl.

2. The compound according to claim 1, which is represented by the following formula (2): In formula (2), R 1 ~R 9 , R 11 ~R 18 , R 21 ~R 27 ,Ar,L 1 , L 22 and L 3 Same as the definition in formula (1).

3. The compound according to claim 1 or 2, which is represented by any one of the following formulas (3) to (6): In formulas (3) to (6), R 1 ~R 9 , R 11 ~R 18 , R 21 ~R 27 ,Ar,L 11 , L 22 and L 33 Same as the definition in formula (1).

4. The compound according to claim 3, which is represented by the formula (3) or (4).

5. The compound according to claim 1 or 2, wherein R 7 or R 8 is a single bond bonded to *a.

6. The compound according to claim 1, which is represented by the following formula (7): In formula (7), R 1 ~R 6 , R 8 , R 9 , R 11 ~R 18 , R 21 ~R 27 ,Ar,L 1 , L 2 and L 3 Same as the definition in formula (1).

7. The compound according to claim 1 or 2, which is represented by the following formula (8): In formula (8), R 1 ~R 6 , R 8 , R 9 , R 11 ~R 18 , R 21 ~R 27 ,Ar,L 1 , L 22 and L 3 Same as the definition in formula (1).

8. The compound according to claim 1 or 2, wherein The unsubstituted aryl group having 6 to 18 ring carbon atoms represented by Ar is selected from the group consisting of phenyl, biphenyl, terphenyl, biphenylenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, phenaltenyl, pyrenyl, chrysene, fluorenyl, fluoranthenyl and triphenylene.

9. The compound according to claim 1 or 2, wherein The unsubstituted aryl group having 6 to 18 ring carbon atoms represented by Ar is selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, phenanthryl and triphenylene.

10. The compound according to claim 1 or 2, wherein L 1 For a single key.

11. The compound according to claim 1, wherein L 2 It is an unsubstituted phenylene group.

12. The compound according to claim 1 or 2, wherein L 3 is a single bond or an unsubstituted phenylene group.

13. The compound according to claim 12, wherein In L 3 When it is a single bond, Ar is selected from biphenyl, terphenyl and naphthyl, In L 3 When Ar is an unsubstituted phenylene group, Ar is selected from naphthyl and phenanthryl.

14. The compound according to claim 1 or 2, wherein R 1 ~R 6 and R which is not a single bond to *a 7 ~R 9 All are hydrogen atoms.

15. The compound according to claim 1 or 2, wherein R 11 ~R 18 All are hydrogen atoms.

16. The compound according to claim 1 or 2, wherein R 21 ~R 27 All are hydrogen atoms.

17. The compound according to claim 1 or 2, wherein the compound is selected from the following compounds, 。 18 . A material for an organic electroluminescent device, comprising the compound according to claim 1 .

19. An organic electroluminescent element comprising a cathode, an anode, and an organic layer located between the cathode and the anode, wherein the organic layer comprises a light-emitting layer, and at least one layer of the organic layer comprises the compound according to any one of claims 1 to 17.

20. The organic electroluminescent element according to claim 19, wherein The organic layer includes a hole transport region between the anode and the light emitting layer, and the hole transport region includes the compound.

21. The organic electroluminescent element according to claim 20, wherein: The hole transport region includes a first hole transport layer on the anode side and a second hole transport layer on the cathode side, and the first hole transport layer, the second hole transport layer, or both contain the compound.

22. The organic electroluminescent element according to claim 21, wherein The first hole transport layer includes the compound.

23. The organic electroluminescent element according to claim 21, wherein The second hole transport layer includes the compound.

24. The organic electroluminescent element according to claim 21, wherein The second hole transport layer is adjacent to the light emitting layer.

25. The organic electroluminescent element according to claim 19, wherein: The light-emitting layer includes a fluorescent dopant material.

26. The organic electroluminescent element according to claim 19, wherein The light-emitting layer includes a phosphorescent dopant material. 27 . An electronic device comprising the organic electroluminescent element according to claim 19 .

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