Organic electroluminescent element and electronic device

Abstract

Provided is an organic electroluminescent element in which an electron-transporting layer contains a compound A represented by formula (1) and a light-emitting layer contains a host material B represented by formula (10), and which has further improved element performance, and an electronic device including the organic electroluminescent element. In the formula, the symbols are the same as defined in the description.

Description

Technical Field

[0001] This invention relates to organic electroluminescent elements and electronic devices comprising such organic electroluminescent elements. Background Technology

[0002] Generally, organic electroluminescent devices (hereinafter sometimes referred to as "organic EL devices") consist of an anode, a cathode, and an organic layer sandwiched between the anode and cathode. When a voltage is applied between the two electrodes, electrons are injected into the luminescent region from the cathode side, and holes are injected into the luminescent region from the anode side. The injected electrons and holes recombine in the luminescent region to generate an excited state, which emits light when it returns to the ground state. Therefore, discovering combinations of materials that efficiently transport electrons or holes to the luminescent region, facilitate electron-hole recombination, and enable efficient exciton emission is crucial for obtaining high-performance organic EL devices.

[0003] Patent documents 1-9 disclose compounds used as materials for organic EL elements and organic EL elements containing the compounds.

[0004] Existing technical documents

[0005] Patent documents

[0006] Patent Document 1: WO2005 / 112519A1

[0007] Patent Document 2: WO2017 / 200210A1

[0008] Patent Document 3: KR2014-0006708

[0009] Patent Document 4: WO2019 / 139419A1

[0010] Patent Document 5: WO2018 / 105888A1

[0011] Patent Document 6: WO2018 / 056645A1

[0012] Patent Document 7: CN107880031

[0013] Patent Document 8: WO2012 / 108881A1

[0014] Patent Document 9: US2014 / 0361268 Summary of the Invention

[0015] The problem the invention aims to solve

[0016] In the past, a large number of compounds for organic EL devices have been reported, but there is still a search for further improvements in the performance of organic EL devices.

[0017] The present invention was made to solve the above-mentioned problems, and aims to provide an organic EL element with further improved element performance by comprising a combination of specific compounds, and an electronic device comprising such an organic EL element.

[0018] means for solving problems

[0019] The inventors have conducted repeated and in-depth studies on the performance of organic EL elements containing compounds described in Patent Documents 1 to 9, and have found that organic EL elements having a hole-blocking layer containing compound A described below and a light-emitting layer containing host material B described below exhibit higher performance.

[0020] In one embodiment, the present invention provides the following organic EL element.

[0021] The organic EL element has a cathode, an anode and an organic layer located between the cathode and the anode. The organic layer includes a light-emitting layer and an electron transport layer. The electron transport layer includes compound A and the light-emitting layer includes host material B. Compound A is represented by formula (1) and host material B is represented by formula (10).

[0022] [Chemical Formula 1]

[0023]

[0024] (in the formula,

[0025] Y 1 and Y 2 One of them is a nitrogen atom, and the other one is a CR atom;

[0026] R is selected from hydrogen atom, substituted or unsubstituted aryl group with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic group with 5 to 50 carbon atoms, substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 50 carbon atoms, fluorine atom and cyano group.

[0027] Ar 1 and Ar 2 Each is independently selected from aryl groups with 6 to 50 cyclic carbon atoms (substituted or unsubstituted) and heterocyclic groups with 5 to 50 cyclic atoms (substituted or unsubstituted);

[0028] L 1 and L 2 Each is an arylene group that is independently either a single bond or substituted or unsubstituted, and has 6 to 50 carbon atoms in a cyclic structure.

[0029] R 1 ~R 6Each is independently selected from hydrogen atoms, substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic groups with 5 to 50 carbon atoms, substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms, fluorine atoms, and cyano groups.

[0030] Selected from R 1 ~R 6 Two adjacent elements in a ring can bond together to form a substituted or unsubstituted ring, or they can not bond together and therefore not form a ring.

[0031] Cz is represented by either equation (1-a) or equation (1-b);

[0032] [Chemical Formula 2]

[0033]

[0034] (in the formula,

[0035] R 21 ~R 28 and R 31 ~R 38 Each is independently a hydrogen atom or a substituent, which is selected from substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic groups with 5 to 50 carbon atoms, substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms, fluorine atoms, and cyano groups.

[0036] Selected from R 21 ~R 28 Two adjacent elements in a ring can bond together to form a substituted or unsubstituted ring, or they can not bond together and therefore not form a ring.

[0037] Selected from R 31 ~R 38 Two adjacent elements in a ring can bond together to form a substituted or unsubstituted ring, or they can not bond together and therefore not form a ring.

[0038] R 24 With R 25 and R 34 With R 35 They can bond with each other to form substituted or unsubstituted rings, or they can not bond with each other and therefore not form rings;

[0039] R a Selected from substituted or unsubstituted aryl groups having 6 to 50 carbon atoms and substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms;

[0040] Selected from R 21 ~R 28 One of them is connected to L via *a 3Bonded single bonds;

[0041] *b indicates that L 3 The location of the bond.

[0042] n is an integer from 1 to 3. When n is 2 or 3, the 2 or 3 Cz are the same or different from each other.

[0043] L 3 and L 4 Each is an arylene group, independently a single bond or substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure, wherein, in the case of n being 2 or 3, L 4 (A substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure.)

[0044] [Chemical Formula 3]

[0045]

[0046] (in the formula,

[0047] Selected from R 101 ~R 110 At least one of them is a group represented by formula (31);

[0048] When there are more than two groups as shown in formula (31), the two or more groups as shown in formula (31) can be the same or different;

[0049] R selected from groups not represented by formula (31) 101 ~R 110 One or more adjacent pairs in a ring can bond together to form a substituted or unsubstituted ring, or they can not bond together and therefore not form a ring;

[0050] R is not a group shown in formula (31) and does not form the above-mentioned ring. 101 ~R 110 Each of the following groups is independently composed of a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group with 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 50 carbon atoms, or a -Si(R group). 901 (R) 902 (R) 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 (R) 907 ), substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms;

[0051] R 901 ~R907 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 cyclic atoms.

[0052] In R 901 ~R 907 In the case of two or more R, two or more R 901 ~R 907 They can be the same or different.

[0053] -L 101 -Ar 101 (31)

[0054] (in the formula,

[0055] L 101 It is a single bond, a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in the cyclic ring, or a divalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms;

[0056] Ar 101 It can be an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted, or a heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0057] In another embodiment, the present invention provides an electronic device comprising the aforementioned organic electroluminescent element.

[0058] The effects of the invention

[0059] Organic EL devices with a hole-blocking layer containing compound A and a light-emitting layer containing host material B exhibit high device performance. Attached Figure Description

[0060] Figure 1 This is a schematic diagram illustrating an example of the layer configuration of an organic EL element according to one aspect of the present invention.

[0061] Figure 2 This is a schematic diagram illustrating another example of the layer configuration of an organic EL element according to one aspect of the present invention. Detailed Implementation

[0062] [definition]

[0063] In this specification, a hydrogen atom means an isotope containing different numbers of neutrons, namely protium, deuterium, and tritium.

[0064] In this specification, the chemical structural formula does not explicitly show that the bonding positions of symbols such as "R" and "D" representing deuterium atoms are set to be bonded to hydrogen atoms, i.e., protium atoms, deuterium atoms, or tritium atoms.

[0065] In this specification, the number of carbon atoms forming a ring refers to the number of carbon atoms in the ring itself of a compound whose atoms are bonded in a ring (e.g., monocyclic compounds, fused-ring compounds, bridged-ring compounds, carbocyclic compounds, and heterocyclic compounds). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of carbon atoms forming the ring. The term "number of carbon atoms forming a ring" is used as described below unless otherwise specified. For example, the number of carbon atoms forming a ring is 6 for a benzene ring, 10 for a naphthalene ring, 5 for a pyridine ring, and 4 for a furan ring. Additionally, for example, the number of carbon atoms forming a ring is 13 for 9,9-diphenylfluoreneyl and 25 for 9,9'-spirobifluoreneyl.

[0066] Furthermore, when a benzene ring is substituted with an alkyl group, the carbon number of the alkyl group is not included in the number of carbon atoms in the ring-forming process of the benzene ring. Therefore, the number of carbon atoms in the cyclic benzene ring substituted with an alkyl group is 6. Similarly, when a naphthalene ring is substituted with an alkyl group, the carbon number of the alkyl group is not included in the number of carbon atoms in the ring-forming process of the naphthalene ring. Therefore, the number of carbon atoms in the cyclic naphthalene ring substituted with an alkyl group is 10.

[0067] In this specification, the number of cyclic atoms refers to the number of atoms constituting the ring itself in compounds with a cyclic structure (e.g., monocyclic, fused-ring, and ring assemblies). Atoms that do not constitute the ring (e.g., hydrogen atoms ending the bonds of the ring-forming atoms) and atoms contained in substituents when the ring is substituted are not included in the number of cyclic atoms. The term "number of cyclic atoms" as used below is the same unless otherwise stated. For example, the number of cyclic atoms in a pyridine ring is 6, in a quinazoline ring it is 10, and in a furan ring it is 5. For example, the number of hydrogen atoms bonded to the pyridine ring or atoms constituting substituents are not included in the number of cyclic atoms in pyridine. Therefore, the number of cyclic atoms in a pyridine ring bonded with hydrogen atoms or substituents is 6. Furthermore, hydrogen atoms bonded to the carbon atoms of the quinazoline ring, or atoms constituting substituents, are not included in the number of cyclic atoms of the quinazoline ring. Therefore, the number of cyclic atoms in a quinazoline ring with bonded hydrogen atoms or substituents is 10.

[0068] In this specification, the phrase "ZZ group with substituted or unsubstituted carbon numbers of XX to YY" indicates the number of carbons when the ZZ group is unsubstituted; the number of carbons of substituents is not included. Here, "YY" is greater than "XX," where "XX" refers to an integer greater than or equal to 1, and "YY" refers to an integer greater than or equal to 2.

[0069] In this specification, the phrase "ZZ group with substituted or unsubstituted atoms of XX to YY" refers to the number of atoms when the ZZ group is unsubstituted, excluding the number of atoms of substituents when substitution has occurred. Here, "YY" is greater than "XX", where "XX" is an integer greater than or equal to 1, and "YY" is an integer greater than or equal to 2.

[0070] In this specification, "unsubstituted ZZ group" means "substituted or unsubstituted ZZ group" as "unsubstituted ZZ group", and "substituted ZZ group" means "substituted or unsubstituted ZZ group" as "substituted ZZ group".

[0071] In this specification, "unsubstituted" when referred to as "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group has not been substituted with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.

[0072] Furthermore, in this specification, "substitution" when expressed as "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group have been replaced by a substituent. Similarly, "substitution" when expressed as "BB group substituted by AA group" also means that one or more hydrogen atoms in the BB group have been replaced by an AA group.

[0073] Substituents described in this specification

[0074] The substituents described in this specification are explained below. Unless otherwise specified, the substituents described in this specification are defined as follows.

[0075] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted aryl group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0076] Unless otherwise stated in this specification, the number of cyclic atoms in the "unsubstituted heterocyclic group" is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0077] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0078] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkenyl group" is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0079] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkynyl group" is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0080] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted cycloalkyl group" is 3 to 50, preferably 3 to 20, and more preferably 3 to 6.

[0081] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted aryl group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0082] Unless otherwise stated in this specification, the number of cyclic atoms in the "unsubstituted divalent heterocyclic group" is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0083] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkylene group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0084] • "Substituted or unsubstituted aryl groups"

[0085] Specific examples of "substituted or unsubstituted aryl" as described in this specification (specific example group G1) include unsubstituted aryl (specific example group G1A) and substituted aryl (specific example group G1B), etc. (Here, unsubstituted aryl refers to the case where "substituted or unsubstituted aryl" is "unsubstituted aryl", and substituted aryl refers to the case where "substituted or unsubstituted aryl" is "substituted aryl".) In this specification, when referred to only as "aryl", both "unsubstituted aryl" and "substituted aryl" are included.

[0086] "Substituted aryl" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl" group have been substituted with a substituent. Examples of "substituted aryl" include the group in Specific Example Group G1A below in which one or more hydrogen atoms of an "unsubstituted aryl" group have been substituted with a substituent, and the substituted aryl group in Specific Example Group G1B below. It should be noted that the examples of "unsubstituted aryl" and "substituted aryl" listed here are only examples. The "substituted aryl" described in this specification also includes the group in Specific Example Group G1B below in which hydrogen atoms bonded to the carbon atom of the aryl group itself have been further substituted with a substituent, and the group in Specific Example Group G1B below in which hydrogen atoms of the substituent have been further substituted with a substituent.

[0087] • Unsubstituted aryl groups (specific example group G1A):

[0088] Phenyl,

[0089] p-phenyl,

[0090] metaphenyl,

[0091] o-phenyl,

[0092] p-terphenyl-4-yl,

[0093] p-terphenyl-3-yl,

[0094] p-terphenyl-2-yl,

[0095] m-terphenyl-4-yl,

[0096] m-terphenyl-3-yl,

[0097] m-terphenyl-2-yl,

[0098] o-terphenyl-4-yl

[0099] o-terphenyl-3-yl

[0100] o-terphenyl-2-yl,

[0101] 1-Naphthyl,

[0102] 2-Naphthyl,

[0103] anthracene,

[0104] Benzanthracene,

[0105] Fiki,

[0106] Benzphenanthrene,

[0107] Finadenyl,

[0108] Pyrene

[0109] base,

[0110] benzo[a] base,

[0111] Tri-phenylene,

[0112] Benzotrimethylene

[0113] phenoxytetraphenyl,

[0114] Pentaphenyl,

[0115] Fluorine

[0116] 9,9'-spirobisfluorene,

[0117] benzo[f]fluorene,

[0118] Dibenzofluorene,

[0119] Fluoranthene group,

[0120] Benzofluoranthyl,

[0121] Perylene and

[0122] The monovalent aryl group is derived by removing one hydrogen atom from the ring structure shown in the following general formulas (TEMP-1) to (TEMP-15).

[0123] [Chemical Formula 4]

[0124]

[0125] [Chemical Formula 5]

[0126]

[0127] • Substituted aryl groups (specific example group G1B):

[0128] o-Tolyl,

[0129] m-Tolyl,

[0130] p-Tolyl,

[0131] p-Xylyl,

[0132] m-Xylyl,

[0133] o-xylyl,

[0134] p-isopropylphenyl,

[0135] m-Isopropylphenyl,

[0136] o-isopropylphenyl,

[0137] p-tert-butylphenyl,

[0138] m-tert-butylphenyl,

[0139] o-tert-butylphenyl,

[0140] 3,4,5-Trimethylphenyl,

[0141] 9,9-Dimethylfluorenyl,

[0142] 9,9-Diphenylfluorenyl

[0143] 9,9-bis(4-methylphenyl)fluorenyl,

[0144] 9,9-Bis(4-isopropylphenyl)fluorenyl,

[0145] 9,9-Bis(4-tert-butylphenyl)fluorenyl,

[0146] cyanophenyl,

[0147] Triphenylsilylphenyl

[0148] Trimethylsilylphenyl

[0149] Phenylacetyl,

[0150] Naphthylphenyl and

[0151] A group derived from the ring structure shown in the above general formulas (TEMP-1) to (TEMP-15) by substitution of one or more hydrogen atoms of a monovalent group with a substituent.

[0152] • "Substituted or unsubstituted heterocyclic groups"

[0153] The term "heterocyclic group" as used in this specification refers to a cyclic group whose cyclic atoms contain at least one heteroatom. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.

[0154] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.

[0155] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0156] Specific examples of "substituted or unsubstituted heterocyclic groups" described in this specification (specific example group G2) include unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B), etc. (Here, unsubstituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group", and substituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group".) In this specification, the term "heterocyclic group" includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group".

[0157] "Substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" have been substituted with a substituent. Specific examples of "substituted heterocyclic groups" include the group in example group G2A below where the hydrogen atoms of the "unsubstituted heterocyclic group" have been substituted, and the example of a substituted heterocyclic group in example group G2B below. It should be noted that the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are only examples. The "substituted heterocyclic groups" described in this specification also include the group in example group G2B where the hydrogen atoms bonded to the cyclic atoms of the heterocyclic group itself have been further substituted with a substituent, and the group in example group G2B where the hydrogen atoms of the substituent have been further substituted with a substituent.

[0158] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1), unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2), unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3), and monovalent heterocyclic groups derived from the ring structures shown in the following general formulas (TEMP-16) to (TEMP-33) by removing one hydrogen atom (specific example group G2A4).

[0159] Specific example group G2B includes, for example, the following: a nitrogen-containing substituted heterocyclic group (specific example group G2B1), an oxygen-containing substituted heterocyclic group (specific example group G2B2), a sulfur-containing substituted heterocyclic group (specific example group G2B3), and a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) have been substituted with a substituent (specific example group G2B4).

[0160] • Unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1):

[0161] pyrrole,

[0162] Imidazole group,

[0163] pyrazolyl,

[0164] Triazole group,

[0165] Tetrazolyl,

[0166] Oxazolyl,

[0167] Isoxazolyl,

[0168] Oxadiazole group,

[0169] Thiazole group,

[0170] Isothiazolyl,

[0171] Thiadiazole group,

[0172] pyridyl,

[0173] pyridazinyl,

[0174] Pyrimidine group,

[0175] Pyrazinyl,

[0176] Triazine group

[0177] Indole,

[0178] Isoindolyl,

[0179] Indazine-based

[0180] Quinazine-based

[0181] Quinoline,

[0182] Isoquinoline,

[0183] Crenoline group

[0184] Phthaloazine

[0185] Quinazolinyl,

[0186] Quinoxaloyl,

[0187] Benzimidazole group,

[0188] Indazole group,

[0189] phenanthroline,

[0190] phenanthridine,

[0191] acridine group,

[0192] Phenazine group,

[0193] Carbazolyl,

[0194] Benzocarbazolyl,

[0195] Morpholinyl,

[0196] phenoxazine group,

[0197] phenothiazine group,

[0198] Azacarbazolyl and diazacarbazolyl.

[0199] • Unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2):

[0200] furanyl,

[0201] Oxazolyl,

[0202] Isoxazolyl,

[0203] Oxadiazole group,

[0204] Xuton base,

[0205] Benzofuranyl,

[0206] Isobenzofuranyl,

[0207] Dibenzofuranyl,

[0208] Naphthobenzofuranyl,

[0209] Benzoxazolyl,

[0210] Benzisoxazole group,

[0211] phenoxazine group,

[0212] Morpholinyl,

[0213] Dinaphthylfuranyl,

[0214] Azadibenzofuranyl,

[0215] diazadibenzofuranyl,

[0216] Azanaphthalenebenzofuranyl and

[0217] Diazanaphthenebenzofuranyl.

[0218] • Unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3):

[0219] Thiophene group

[0220] Thiazole group,

[0221] Isothiazolyl,

[0222] Thiadiazole group,

[0223] benzothienyl

[0224] isobenzothienyl

[0225] dibenzothienyl

[0226] Naphthobenzothienyl

[0227] Benzothiazolyl,

[0228] Benzisothiazolyl,

[0229] phenothiazine group,

[0230] dinaphthothienyl

[0231] azadibenzothienyl

[0232] diazadibenzothienyl

[0233] Azanaphthobenzothienyl, and

[0234] diazanaphthobenzothienyl.

[0235] • The monovalent heterocyclic group derived by removing one hydrogen atom from the ring structures shown in the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0236] [Chemical Formula 6]

[0237]

[0238] [Chemical Formula 7]

[0239]

[0240] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each can be independently composed of an oxygen atom, a sulfur atom, NH, or CH2. Among them, X... A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH.

[0241] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A When at least one of them is NH or CH2, the monovalent heterocyclic group derived from the ring structure shown in the above general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0242] • Heterocyclic groups containing nitrogen atoms (specific example group G2B1):

[0243] (9-phenyl)carbazole group,

[0244] (9-Biphenyl)carbazolyl,

[0245] (9-Phenyl)phenylcarbazolyl,

[0246] (9-Naphthyl)carbazole,

[0247] Diphenylcarbazole-9-yl,

[0248] Phenylexacarbazole-9-yl,

[0249] Methylbenzimidazole,

[0250] Ethylbenzimidazole,

[0251] Phenylacetyl,

[0252] Biphenyltriazine

[0253] diphenyltriazine group,

[0254] phenylquinazolinyl and

[0255] Biphenylquinazolinyl.

[0256] • Heterocyclic groups containing oxygen atoms (specific example group G2B2):

[0257] Phenyl dibenzofuranyl,

[0258] Methyldibenzofuranyl,

[0259] tert-butyldibenzofuranyl and

[0260] The monovalent residue of [9H-xanton-9,9'-[9H]fluorene].

[0261] • Heterocyclic groups containing sulfur atoms (specific example group G2B3):

[0262] Phenyl dibenzothiophene,

[0263] Methyldibenzothiophene,

[0264] tert-butyldibenzothiophene and

[0265] The monovalent residue of [9H-thiophene-9,9'-[9H]fluorene].

[0266] • Groups derived from the ring structures shown in the above general formulas (TEMP-16) to (TEMP-33) in which one or more hydrogen atoms of a monovalent heterocyclic group have been substituted with substituents (specific example group G2B4):

[0267] The aforementioned "one or more hydrogen atoms of a monovalent heterocyclic group" refers to one or more hydrogen atoms selected from the following: hydrogen atoms bonded to the cyclic carbon atom of the monovalent heterocyclic group, hydrogen atoms bonded to the nitrogen atom when at least one of XA and YA is NH, and hydrogen atoms of the methylene group when one of XA and YA is CH2.

[0268] • "Substituted or unsubstituted alkyl groups"

[0269] As specific examples of "substituted or unsubstituted alkyl" described in this specification (specific example group G3), the following unsubstituted alkyl (specific example group G3A) and substituted alkyl (specific example group G3B) can be cited. (Here, unsubstituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "substituted alkyl".) Hereinafter, when referred to as "alkyl", both "unsubstituted alkyl" and "substituted alkyl" are included.

[0270] "Substituted alkyl" refers to a group in which one or more hydrogen atoms of an "unsubstituted alkyl" have been substituted with a substituent. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms of an "unsubstituted alkyl" (specific example group G3A) have been substituted with a substituent, and examples of substituted alkyl (specific example group G3B). In this specification, "unsubstituted alkyl" refers to a chain-like alkyl group. Therefore, "unsubstituted alkyl" includes both straight-chain and branched-chain unsubstituted alkyl groups. It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples; the "substituted alkyl" described in this specification also includes groups in which the hydrogen atoms of the alkyl group in specific example group G3B have been further substituted with a substituent, and groups in which the hydrogen atoms of the substituents in specific example group G3B have been further substituted with a substituent.

[0271] • Unsubstituted alkyl groups (specific example group G3A):

[0272] methyl,

[0273] Ethyl,

[0274] n-propyl,

[0275] Isopropyl,

[0276] n-Butyl,

[0277] Isobutyl,

[0278] sec-butyl, and

[0279] tert-butyl.

[0280] • Substituted alkyl groups (specific example group G3B):

[0281] Heptafluoropropyl (including isomers),

[0282] Pentafluoroethyl,

[0283] 2,2,2-Trifluoroethyl and

[0284] Trifluoromethyl

[0285] • "Substituted or unsubstituted alkenyl groups"

[0286] Specific examples of "substituted or unsubstituted alkenyl groups" (specific example group G4) described in this specification include unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc. (Here, "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "unsubstituted alkenyl group", and "substituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "substituted alkenyl group".) In this specification, when simply referred to as "alkenyl group", both "unsubstituted alkenyl group" and "substituted alkenyl group" are included.

[0287] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" group have been substituted with a substituent. Specific examples of "substituted alkenyl" include the "unsubstituted alkenyl" group (specific example group G4A) having a substituent and examples of substituted alkenyl groups (specific example group G4B). It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples; the "substituted alkenyl" described in this specification also includes groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the alkenyl itself have been further substituted with a substituent, and groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the substituent have been further substituted with a substituent.

[0288] • Unsubstituted alkenyl groups (specific example group G4A):

[0289] vinyl,

[0290] Allyl

[0291] 1-Butenyl,

[0292] 2-Butenyl and

[0293] 3-Butenyl.

[0294] • Substituted alkenyl groups (specific example group G4B):

[0295] 1,3-Butadienyl,

[0296] 1-Methylvinyl

[0297] 1-Methylallyl,

[0298] 1,1-Dimethylallyl,

[0299] 2-Methylallyl and

[0300] 1,2-Dimethylallyl.

[0301] • "Substituted or unsubstituted alkynyl groups"

[0302] As specific examples of "substituted or unsubstituted alkynyl groups" described in this specification (specific example group G5), the following unsubstituted alkynyl groups (specific example group G5A) can be cited. (Here, unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group".) The following description of "alkynyl group" includes both "unsubstituted alkynyl group" and "substituted alkynyl group".

[0303] "Substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" have been replaced by a substituent. Specific examples of "substituted alkynyl group" include groups in which one or more hydrogen atoms in an "unsubstituted alkynyl group" (specific example group G5A) have been replaced by a substituent.

[0304] • Unsubstituted alkynyl group (specific example group G5A):

[0305] Acetylene

[0306] • "Substituted or unsubstituted cycloalkyl groups"

[0307] Specific examples of "substituted or unsubstituted cycloalkyl" described in this specification (specific example group G6) include unsubstituted cycloalkyl (specific example group G6A) and substituted cycloalkyl (specific example group G6B), etc. (Here, unsubstituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and substituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl".) In this specification, when referred to only as "cycloalkyl", both "unsubstituted cycloalkyl" and "substituted cycloalkyl" are included.

[0308] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group have been substituted with a substituent. Specific examples of "substituted cycloalkyl" include the group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group (specific example group G6A) have been substituted with a substituent, and examples of substituted cycloalkyl groups (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples. The "substituted cycloalkyl" described in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl" group of specific example group G6B have been substituted with a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted cycloalkyl" group of specific example group G6B have been further substituted with a substituent.

[0309] • Unsubstituted cycloalkyl groups (specific example group G6A):

[0310] Cyclopropyl

[0311] Cyclobutyl,

[0312] Cyclopentyl,

[0313] Cyclohexyl,

[0314] 1-Adamantyl,

[0315] 2-Adamantyl,

[0316] 1-norborneol and

[0317] 2-norborneol.

[0318] • Substituted cycloalkyl groups (specific example group G6B):

[0319] 4-Methylcyclohexyl.

[0320] ·"-Si(R 901 (R) 902 (R) 903 The group shown in the figure”

[0321] As described in this specification, -Si(R) 901 (R) 902 (R) 903 Specific examples of the group shown in the figure (specific example group G7) can be given as follows:

[0322] -Si(G1)(G1)(G1),

[0323] -Si(G1)(G2)(G2),

[0324] -Si(G1)(G1)(G2),

[0325] -Si(G2)(G2)(G2),

[0326] -Si(G3)(G3)(G3), and

[0327] -Si(G6)(G6)(G6)

[0328] Here,

[0329] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0330] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0331] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0332] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0333] In -Si(G1)(G1)(G1), multiple G1s may be the same or different from each other.

[0334] In -Si(G1)(G2)(G2), multiple G2s may be the same or different from each other.

[0335] In -Si(G1)(G1)(G2), multiple G1s may be the same or different from each other.

[0336] In -Si(G2)(G2)(G2), multiple G2s may be the same or different from each other.

[0337] In -Si(G3)(G3)(G3), multiple G3s may be the same or different from each other.

[0338] In -Si(G6)(G6)(G6), multiple G6s may be the same or different from each other.

[0339] ·“-O-(R 904 The group shown in the figure”

[0340] As described in this specification, -O-(R) 904 Specific examples of the group shown (specific example group G8) can be given as follows:

[0341] -O(G1)

[0342] -O(G2),

[0343] -O(G3) and

[0344] -O(G6).

[0345] Here,

[0346] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0347] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0348] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0349] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0350] ·“-S-(R 905 The group shown in the figure”

[0351] As described in this specification, -S-(R) 905 Specific examples of the group shown (specific example group G9) can be given as follows:

[0352] -S(G1)

[0353] -S(G2),

[0354] -S(G3) and

[0355] -S(G6).

[0356] Here,

[0357] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0358] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0359] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0360] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0361] ·"-N(R 906 (R) 907 The group shown in the figure”

[0362] As described in this specification, -N(R) 906 (R) 907 Specific examples of the group shown (specific example group G10) can be given as follows:

[0363] -N(G1)(G1),

[0364] -N(G2)(G2),

[0365] -N(G1)(G2),

[0366] -N(G3)(G3) and

[0367] -N(G6)(G6).

[0368] Here,

[0369] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0370] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0371] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0372] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0373] In -N(G1)(G1), multiple G1s may be the same or different from each other.

[0374] In -N(G2)(G2), multiple G2 values ​​may be the same or different from each other.

[0375] In -N(G3)(G3), multiple G3s may be the same or different from each other.

[0376] In -N(G6)(G6), multiple G6 values ​​may be the same or different from each other.

[0377] • "Halogen atom"

[0378] Specific examples of "halogen atoms" described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0379] • "Substituted or unsubstituted fluoroalkyl groups"

[0380] The term "substituted or unsubstituted fluoroalkyl" as used in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom constituting the alkyl group has been replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group have been replaced by fluorine atoms (perfluorinated groups). Unless otherwise specified in this specification, the number of carbon atoms in an "unsubstituted fluoroalkyl" group is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted fluoroalkyl" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl" group have been replaced by a substituent. It should be noted that the term "substituted fluoroalkyl" as used in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in a "substituted fluoroalkyl" group have been further replaced by a substituent, and groups in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl" group have been further replaced by a substituent. As a specific example of "unsubstituted fluoroalkyl", examples can be given of groups in which one or more hydrogen atoms in the above-mentioned "alkyl" (specific example group G3) have been replaced by fluorine atoms.

[0381] • "Substituted or unsubstituted haloalkyl groups"

[0382] The term "substituted or unsubstituted haloalkyl" as used in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom constituting the alkyl group has been replaced by a halogen atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group have been replaced by halogen atoms. Unless otherwise specified in this specification, the number of carbon atoms in an "unsubstituted haloalkyl" group is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted haloalkyl" refers to a group in which one or more hydrogen atoms of a "haloalkyl" group have been replaced by a substituent. It should be noted that "substituted haloalkyl" as used in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in a "substituted haloalkyl" group have been further replaced by a substituent, and groups in which one or more hydrogen atoms of a substituent in a "substituted haloalkyl" group have been further replaced by a substituent. As a specific example of "unsubstituted haloalkyl", examples can be given of groups in which one or more hydrogen atoms of the above-mentioned "alkyl" (specific example group G3) have been substituted with halogen atoms. Haloalkyl is sometimes called haloalkyl.

[0383] • "Substituted or unsubstituted alkoxy groups"

[0384] As a specific example of "substituted or unsubstituted alkoxy group" as described in this specification, it is the group indicated by -O (G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0385] • "Substituted or unsubstituted alkylthio groups"

[0386] As a specific example of "substituted or unsubstituted alkylthio group" as described in this specification, it is the group indicated by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0387] • "Substituted or unsubstituted aryloxy groups"

[0388] As a specific example of "substituted or unsubstituted aryloxy group" as described in this specification, it is the group indicated by -O (G1), where G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of carbon atoms in the ring of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0389] • "Substituted or unsubstituted arylthio groups"

[0390] As a specific example of "substituted or unsubstituted arylthio group" as described in this specification, it is the group indicated by -S(G1), where G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of carbon atoms in the ring of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0391] • "Substituted or unsubstituted trialkylsilyl groups"

[0392] As a specific example of "trialkylsilyl" as described in this specification, it is the group represented by -Si(G3)(G3)(G3), where G3 refers to the "substituted or unsubstituted alkyl" described in the specific example group G3. The plurality of G3s in -Si(G3)(G3)(G3) may be identical or different from each other. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the "trialkylsilyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0393] • "Substituted or unsubstituted aralkyl groups"

[0394] As a specific example of "substituted or unsubstituted aralkyl" as described in this specification, it is the group shown as -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl" described in specific example group G3, and G1 is the "substituted or unsubstituted aryl" described in specific example group G1. Therefore, "aralkyl" is a group in which the hydrogen atom of "alkyl" is replaced by "aryl" as a substituent, and is one embodiment of "substituted alkyl". "Unsubstituted aralkyl" is an "unsubstituted alkyl" that is substituted with "unsubstituted aryl", and the number of carbon atoms of "unsubstituted aralkyl" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.

[0395] Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl.

[0396] Unless otherwise specified in this specification, the substituted or unsubstituted aryl groups described herein are preferably phenyl, p-phenyl, meta-phenyl, o-phenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthraceneyl, phenanthryl, pyreneyl, etc. It includes methyl, triphenyl, fluorenyl, 9,9'-spirobisfluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl, etc.

[0397] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic groups described herein are preferably pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, phenanthrolinel, carbazole (1-carbazole, 2-carbazole, 3-carbazole, 4-carbazole or 9-carbazole), benzocarbazole, azacarbazole, diazacarbazole, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophene, and naphtho-benzofuranyl. Benzothiophene, azadibenzothiophene, diazadibenzothiophene, (9-phenyl)carbazoyl ((9-phenyl)carbazo-1-yl, (9-phenyl)carbazo-2-yl, (9-phenyl)carbazo-3-yl or (9-phenyl)carbazo-4-yl), (9-biphenyl)carbazoyl, (9-phenyl)phenylcarbazoyl, diphenylcarbazo-9-yl, phenylcarbazo-9-yl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenyldibenzofuranyl and phenyldibenzothiophene, etc.

[0398] In this specification, the carbazoyl group, unless otherwise specified herein, specifically refers to any one of the following groups.

[0399] [Chemical Formula 8]

[0400]

[0401] In this specification, (9-phenyl)carbazolyl refers specifically to any one of the following groups unless otherwise specified herein.

[0402] [Chemical Formula 9]

[0403]

[0404] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.

[0405] In this specification, dibenzofuranyl and dibenzothiopheneyl are specifically any one of the following groups unless otherwise stated in this specification.

[0406] [Chemical Formula 10]

[0407]

[0408] In the above general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.

[0409] Unless otherwise specified in this specification, the substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and tert-butyl.

[0410] • "Substituted or unsubstituted aryl groups"

[0411] Unless otherwise stated, the "substituted or unsubstituted aryl group" described in this specification is a divalent group derived from the "substituted or unsubstituted aryl group" by removing one hydrogen atom from the aromatic ring. Specific examples of "substituted or unsubstituted aryl group" (specific example group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in specific example group G1 by removing one hydrogen atom from the aromatic ring.

[0412] • "Substituted or unsubstituted divalent heterocyclic groups"

[0413] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification refers to a divalent group derived from the aforementioned "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom from the heterocycle. Specific examples of "substituted or unsubstituted divalent heterocyclic groups" (specific example group G13) include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in specific example group G2 by removing one hydrogen atom from the heterocycle.

[0414] • "Substituted or unsubstituted alkylene compounds"

[0415] Unless otherwise stated, "substituted or unsubstituted alkylene" as described in this specification refers to a divalent group derived from the aforementioned "substituted or unsubstituted alkyl" by removing one hydrogen atom from the alkyl chain. Specific examples of "substituted or unsubstituted alkylene" (Specific Example Group G14) include divalent groups derived from the "substituted or unsubstituted alkyl" described in Specific Example Group G3 by removing one hydrogen atom from the alkyl chain.

[0416] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described herein is preferably any one of the groups in the following general formulas (TEMP-42) to (TEMP-68).

[0417] [Chemical Formula 11]

[0418]

[0419] [Chemical Formula 12]

[0420]

[0421] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0422] In the above general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.

[0423] [Chemical Formula 13]

[0424]

[0425] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0426] Formulas Q9 and Q 10 They can form rings by bonding with each other via single bonds.

[0427] In the above general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.

[0428] [Chemical Formula 14]

[0429]

[0430] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0431] In the above general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.

[0432] Unless otherwise specified in this specification, the substituted or unsubstituted divalent heterocyclic group described herein is preferably any group of the following general formulas (TEMP-69) to (TEMP-102).

[0433] [Chemical Formula 15]

[0434]

[0435] [Chemical Formula 16]

[0436]

[0437] [Chemical Formula 17]

[0438]

[0439] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0440] [Chemical Formula 18]

[0441]

[0442] [Chemical Formula 19]

[0443]

[0444] [Chemical Formula 20]

[0445]

[0446] [Chemical Formula 21]

[0447]

[0448] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0449] The above is an explanation of "substituents described in this specification".

[0450] • "Cases where bonds form rings"

[0451] In this specification, the description of "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring, or bonded together to form a substituted or unsubstituted fused ring, or not bonded together" refers to the cases of "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring", "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted fused ring", and "one or more groups of two or more adjacent elements not bonded together".

[0452] The following description addresses the cases where "one or more groups of two or more adjacent rings are bonded together to form a substituted or unsubstituted monocyclic ring" and "one or more groups of two or more adjacent rings are bonded together to form a substituted or unsubstituted fused ring" (hereinafter, these cases are sometimes collectively referred to as "the case of forming a ring by bonding"). The case of anthracene compounds with the following general formula (TEMP-103) whose parent skeleton is anthracene ring will be used as an example.

[0453] [Chemical Formula 22]

[0454]

[0455] For example, in R 921 ~R 930 In the case of "one or more groups of two or more adjacent elements bonded together to form a loop", the group consisting of two adjacent elements as a group refers to R. 921 With R 922 group, R 922 With R 923 group, R 923 With R 924 group, R 924 With R 930 group, R 930 With R 925 group, R 925 With R 926 group, R 926 With R 927 group, R 927 With R 928 group, R 928 With R 929 The group, and R 929 With R 921 The group.

[0456] The phrase "one or more groups" refers to the fact that two or more of the aforementioned adjacent groups can simultaneously form a loop. For example, in R... 921 With R 922 They bond together to form a ring Q A Moreover, R 925 With R 926 They bond together to form a ring Q B In this case, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0457] [Chemical Formula 23]

[0458]

[0459] The formation of rings from "groups of two or more adjacent elements" includes not only the case of bonds formed by groups of "two" adjacent elements, as in the previous example, but also the case of bonds formed by groups of "three or more" adjacent elements. For example, it refers to R... 921 With R 922 They bond together to form a ring Q A And R 922 With R 923 They bond together to form a ring Q C , consisting of 3 adjacent (R) 921 R 922 and R 923When the groups of components Q bond together to form a ring and fuse to the anthracene matrix, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q... A and ring Q C There are a total of R 922 .

[0460] [Chemical Formula 24]

[0461]

[0462] In the formed "single ring" or "fused ring," the structure of the ring alone can be either a saturated ring or an unsaturated ring. Even when "one of the groups of two adjacent rings" forms a "single ring" or "fused ring," that "single ring" or "fused ring" can form either a saturated ring or an unsaturated ring. For example, the ring Q formed in the above general formula (TEMP-104) A and ring Q B Each is either a "single ring" or a "fused ring". Additionally, the ring Q formed in the above general formula (TEMP-105) A and Q ring C It is a "fused ring". The ring Q of the above general formula (TEMP-105) A With ring Q C Through ring Q A With ring Q C Fusing together forms a fused ring. The ring Q of the above general formula (TMEP-104) A If it is a benzene ring, then ring Q A It is a single ring. The ring Q in the above general formula (TMEP-104) A If it is a naphthalene ring, then ring Q A It is a fused ring.

[0463] "Unsaturated rings" refer to aromatic hydrocarbon rings or aromatic heterocycles. "Saturated rings" refer to aliphatic hydrocarbon rings or non-aromatic heterocycles.

[0464] As a specific example of an aromatic hydrocarbon ring, the structure formed by the hydrogen atom-terminated group in specific example group G1 can be cited.

[0465] As a specific example of an aromatic heterocycle, one can cite the structure formed by end-capping an aromatic heterocycle group with hydrogen atoms in specific example group G2.

[0466] As a specific example of an aliphatic hydrocarbon ring, the structure formed by the hydrogen atom-terminated group in specific example group G6 can be cited.

[0467] "Ring formation" refers to the formation of a ring solely by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton forming a ring with one or more other optional elements. For example, R shown in the above general formula (TEMP-104) 921 With R 922 The ring Q formed by mutual bonding A It refers to R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 The carbon atoms of the bonded anthracene framework form rings with one or more optional elements. As a specific example, in the case of R... 921 With R 922 Forming ring Q A In the case of R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 When the bonded anthracene skeleton carbon atoms and 4 carbon atoms form a monocyclic unsaturated ring, R 921 With R 922 The resulting ring is a benzene ring.

[0468] Here, "optional element" is preferably selected from at least one element chosen from the group consisting of carbon, nitrogen, oxygen, and sulfur, unless otherwise specified in this specification. In the case of optional elements (e.g., carbon or nitrogen), non-ring bonds can be capped by hydrogen atoms or replaced by "optional substituents" described later. When optional elements other than carbon are included, the resulting ring is a heterocycle.

[0469] Unless otherwise specified in this specification, the "one or more optional elements" constituting a monocyclic or fused ring are preferably two or more and 15 or less, more preferably three or more and 12 or less, and even more preferably three or more and 5 or less.

[0470] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".

[0471] Unless otherwise stated in this specification, "unsaturated ring" is preferred over "saturated ring".

[0472] Unless otherwise stated in this specification, "monocyclic" is preferably a benzene ring.

[0473] Unless otherwise stated in this specification, the "unsaturated ring" is preferably a benzene ring.

[0474] In the case of "one or more groups of two or more adjacent atoms forming a substituted or unsubstituted monocyclic ring" or "a substituted or unsubstituted fused ring formed by mutual bonding", unless otherwise stated in this specification, it is preferred that one or more groups of two or more adjacent atoms form an unsaturated ring formed by mutual bonding of a plurality of atoms of a parent skeleton and at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur.

[0475] When the aforementioned "monocyclic" or "fused-ring" rings have substituents, the substituents are, for example, the "optional substituents" described later. Specific examples of substituents when the aforementioned "monocyclic" or "fused-ring" rings have substituents are the substituents described in the section "Substituents Represented in This Specification" above.

[0476] When the aforementioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of substituents when the aforementioned "monocyclic" or "fused ring" has a substituent are the substituents described in the section "Substituents Represented in This Specification" above.

[0477] The above explains the cases of "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring" and "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted fused ring" ("the case of bonding to form a ring").

[0478] Substituents when described as "substituted or unsubstituted"

[0479] In one embodiment of this specification, the substituents described above as "substituted or unsubstituted" (sometimes referred to as "optional substituents" in this specification) are, for example, selected from unsubstituted alkyl groups having 1 to 50 carbon atoms.

[0480] Unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0481] Unsubstituted acetylinyl groups with 2 to 50 carbon atoms

[0482] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0483] -Si(R 901 (R) 902 (R) 903 ),

[0484] -O-(R 904 ),

[0485] -S-(R 905 ),

[0486] -N(R 906 (R) 907 ),

[0487] Halogen atom, cyano group, nitro group,

[0488] Unsubstituted aryl groups with 6 to 50 carbon atoms and

[0489] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms

[0490] Groups, etc., in the composition group

[0491] Here, R 901 ~R 907 Each independently

[0492] hydrogen atom,

[0493] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0494] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0495] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0496] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0497] In R 901 In cases where there are two or more R's, there are two or more R's. 901 They are the same or different.

[0498] In R 902 In cases where there are two or more R's, there are two or more R's. 902 They are the same or different.

[0499] In R 903 In cases where there are two or more R's, there are two or more R's. 903 They are the same or different.

[0500] In R 904 In cases where there are two or more R's, there are two or more R's. 904 They are the same or different.

[0501] In R 905 In cases where there are two or more R's, there are two or more R's. 905 They are the same or different.

[0502] In R 906 In cases where there are two or more R's, there are two or more R's. 906 They are the same or different.

[0503] In R907 In cases where there are two or more R's, there are two or more R's. 907 They are the same or different.

[0504] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.

[0505] Alkyl groups with 1 to 50 carbon atoms

[0506] Aryl groups with 6 to 50 carbon atoms and

[0507] Heterocyclic groups with 5 to 50 cyclic atoms

[0508] The groups in the group.

[0509] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.

[0510] Alkyl groups having 1 to 18 carbon atoms

[0511] aryl groups with 6 to 18 carbon atoms and

[0512] Heterocyclic groups with 5 to 18 cyclic atoms

[0513] The groups in the group.

[0514] Specific examples of the substituents mentioned above are those described in the section "Substituents as set forth in this specification".

[0515] Unless otherwise stated in this specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring" with each other, preferably forming a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably forming a benzene ring.

[0516] Unless otherwise stated in this specification, optional substituents may also have other substituents. Any further substituents that may be present as optional substituents are the same as those described above.

[0517] In this specification, the numerical range referred to as "AA~BB" refers to the range included by taking the value AA recorded before "AA~BB" as the lower limit and the value BB recorded after "AA~BB" as the upper limit.

[0518] The organic EL element of the present invention has a cathode, an anode, and an organic layer located between the cathode and the anode. The organic layer includes a light-emitting layer and an electron transport layer. The electron transport layer includes compound A, and the light-emitting layer includes a host material B.

[0519] Compound A

[0520] Compound A, represented by formula (1), is used in the electron transport layer.

[0521] [Chemical Formula 25]

[0522]

[0523] (in the formula,

[0524] Y 1 and Y 2 One of them is a nitrogen atom, and the other one is a CR atom;

[0525] R is selected from hydrogen atom, substituted or unsubstituted aryl group with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic group with 5 to 50 carbon atoms, substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 50 carbon atoms, fluorine atom and cyano group.

[0526] Ar 1 and Ar 2 Each is independently selected from aryl groups with 6 to 50 cyclic carbon atoms (substituted or unsubstituted) and heterocyclic groups with 5 to 50 cyclic atoms (substituted or unsubstituted);

[0527] L 1 and L 2 Each is an arylene group that is independently either a single bond or substituted or unsubstituted, and has 6 to 50 carbon atoms in a cyclic structure.

[0528] R 1 ~R 6 Each is independently selected from hydrogen atoms, substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic groups with 5 to 50 carbon atoms, substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms, fluorine atoms, and cyano groups.

[0529] Selected from R 1 ~R 6 Two adjacent elements in a ring can bond together to form a substituted or unsubstituted ring, or they can not bond together and therefore not form a ring.

[0530] Cz is represented by either equation (1-a) or equation (1-b);

[0531] [Chemical Formula 26]

[0532]

[0533] (in the formula,

[0534] R 21 ~R 28 and R 31 ~R38 Each is independently a hydrogen atom or a substituent, which is selected from substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic groups with 5 to 50 carbon atoms, substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms, fluorine atoms, and cyano groups.

[0535] Selected from R 21 ~R 28 Two adjacent elements in a ring can bond together to form a substituted or unsubstituted ring, or they can not bond together and therefore not form a ring.

[0536] Selected from R 31 ~R 38 Two adjacent elements in a ring can bond together to form a substituted or unsubstituted ring, or they can not bond together and therefore not form a ring.

[0537] R 24 With R 25 and R 34 With R 35 They can bond with each other to form substituted or unsubstituted rings, or they can not bond with each other and therefore not form rings.

[0538] R a Selected from substituted or unsubstituted aryl groups having 6 to 50 carbon atoms and substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms;

[0539] Selected from R 21 ~R 28 One of them is connected to L via *a 3 Bonded single bonds;

[0540] *b indicates that L 3 The location of the bond.

[0541] n is an integer from 1 to 3. When n is 2 or 3, the 2 or 3 Cz are the same or different from each other.

[0542] L 3 and L 4 Each is an arylene group, independently a single bond or substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure, wherein, in the case of n being 2 or 3, L 4 (A substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure.)

[0543] The symbols in formula (1) and the following formulas representing compound A will be explained below. It should be noted that, unless otherwise specified, the same symbols have the same meaning.

[0544] Y 1 and Y 2 One of them is a nitrogen atom, and the other is a CR atom. That is, Y1 It is a nitrogen atom and Y 2 For CR, or Y 1 For CR and Y 2w Nitrogen atom.

[0545] n is an integer from 1 to 3, preferably 1 or 2, and more preferably 1. When n is 2 or 3, the 2 or 3 Cz are the same or different from each other.

[0546] R is selected from hydrogen atom, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, fluorine atom, and cyano group, preferably selected from hydrogen atom, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms, and substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, more preferably hydrogen atom.

[0547] The details of the substituted or unsubstituted aryl groups with 6 to 50 carbon atoms are the same as those described in "Substituents Recorded in this Specification", and are more preferably phenyl, p-phenyl, meta-phenyl, o-phenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, fluorenyl, 9,9'-spirobisfluorenyl, 9,9-dimethylfluorenyl or 9,9-diphenylfluorenyl, and even more preferably phenyl, p-phenyl, meta-phenyl, o-phenyl, 1-naphthyl, 2-naphthyl, fluorenyl, 9,9'-spirobisfluorenyl, 9,9-dimethylfluorenyl or 9,9-diphenylfluorenyl.

[0548] The details of the heterocyclic groups with 5 to 50 cyclic atoms, whether substituted or unsubstituted, are the same as those described in "Substituents Described in this Specification". More preferably, they are carbazolyl (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl or 9-carbazolyl), dibenzofuranyl, naphthobenzofuranyl, dibenzothiophenyl, naphthobenzothiophenyl, phenyldibenzofuranyl or phenyldibenzothiophenyl, and even more preferably carbazolyl (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl or 9-carbazolyl), dibenzofuranyl or dibenzothiophenyl.

[0549] The details of the substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms are the same as those described in "Substituents as described in this specification", preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, more preferably methyl, isopropyl or tert-butyl.

[0550] The details of the substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms are the same as those described in "Substituents described in this specification", preferably cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, more preferably cyclopropyl, cyclopentyl or cyclohexyl.

[0551] R 1 ~R 6 Each atom is independently selected from hydrogen atoms, substituted or unsubstituted aryl groups having 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic groups having 5 to 50 carbon atoms, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, fluorine atoms, and cyano groups, preferably selected from hydrogen atoms, substituted or unsubstituted aryl groups having 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic groups having 5 to 50 carbon atoms, and substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, more preferably hydrogen atoms. R 1 ~R 6 All are hydrogen atoms.

[0552] The details of the substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, the substituted or unsubstituted heterocyclic groups with 5 to 50 carbon atoms, the substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, and the substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms are the same as the details of the corresponding groups described above for R.

[0553] Selected from R 1 ~R 6 The two adjacent ones in the middle, that is, selected from R 1 With R 2 R 3 With R 4 R 4 With R 5 and R 5 With R 6 At least one group of two adjacent elements can be bonded to each other to form a ring, or they can not be bonded to each other and thus not form a ring, preferably not bonded to each other and thus not form a ring.

[0554] The substituted or unsubstituted rings mentioned above are selected from substituted or unsubstituted aromatic hydrocarbon rings, substituted or unsubstituted aliphatic hydrocarbon rings, substituted or unsubstituted aromatic heterocycles, and substituted or unsubstituted aliphatic heterocycles, preferably substituted or unsubstituted aromatic hydrocarbon rings.

[0555] The aforementioned aromatic hydrocarbon rings include, for example, benzene rings, biphenylene rings, naphthalene rings, anthracene rings, benzo[a]anthracene rings, phenanthrene rings, benzo[a]phenanthrene rings, finasteride rings, and pyrene rings. The ring, 1,1-dimethylindene ring, or triphenylene ring, preferably a benzene ring or a naphthalene ring, more preferably a benzene ring.

[0556] The aforementioned aliphatic hydrocarbon rings are, for example, cyclopentene rings, cyclopentadiene rings, cyclohexene rings, cyclohexadiene rings, or aliphatic hydrocarbon rings obtained by partially hydrogenating the aforementioned aromatic hydrocarbon rings.

[0557] The aforementioned aromatic heterocycles include, for example, pyrrole rings, furan rings, thiophene rings, pyridine rings, imidazole rings, pyrazole rings, indole rings, isoindole rings, benzofuran rings, isobenzofuran rings, benzothiophene rings, benzimidazole rings, indazole rings, dibenzofuran rings, naphthobenzofuran rings, dibenzothiophene rings, naphthobenzothiophene rings, carbazole rings, or benzocarbazole rings.

[0558] The aforementioned aliphatic heterocycle is, for example, an aliphatic heterocycle obtained by partially hydrogenating the aforementioned aromatic heterocycle.

[0559] L 3 and L 4 Each is an arylene group that is independently a single bond or substituted or unsubstituted cyclic carbon group with 6 to 50 carbon atoms.

[0560] Where n is 2 or 3, L 4 It is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure.

[0561] In one aspect of the invention, L 3 and L 4 Preferably, each arylene group is independently substituted or unsubstituted, and has 6 to 50 cyclic carbon atoms.

[0562] In another aspect of the invention, L is preferred. 3 It is a single bond and L 4 It is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure.

[0563] In another embodiment of the invention, L 3 and L 4 Single bonds are preferred.

[0564] L 3 and L 4 The details of the substituted or unsubstituted aryl groups with 6 to 50 carbon atoms are the same as those described in "Substituents described in this specification". Examples include the divalent groups derived from the above-mentioned "substituted or unsubstituted aryl groups with 6 to 50 carbon atoms" by removing one hydrogen atom from the aromatic ring.

[0565] L 3 and L 4 The unsubstituted or unsubstituted arylene group representing a cyclic carbon number of 6 to 50 is preferably selected independently from phenylene, biphenylene, naphthylene, phenanthrene, anthracene, and fluoranthracene.

[0566] Ar 1 and Ar2 Each is independently selected from aryl groups with 6 to 50 cyclic carbon atoms (substituted or unsubstituted) and heterocyclic groups with 5 to 50 cyclic atoms (substituted or unsubstituted).

[0567] The details of the substituted or unsubstituted aryl groups with 6 to 50 carbon atoms described above are the same as the details of the corresponding groups described above for R.

[0568] Ar 1 and Ar 2 The unsubstituted aryl group representing the substituted or unsubstituted cyclic carbon number of 6 to 50 is preferably selected independently from phenyl, biphenyl, naphthyl, phenanthryl, anthracene, and fluoranthyl.

[0569] The details of the aforementioned substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms are the same as the details of the corresponding groups described above for R.

[0570] Ar 1 and Ar 2 The unsubstituted heterocyclic group representing the substituted or unsubstituted heterocyclic group with 5 to 50 cyclic atoms is preferably selected independently from pyridyl, pyrimidinyl, triazine, quinolinyl, dibenzothiophene, dibenzofuranyl, azadibenzofuranyl, and azadibenzothiophene.

[0571] L 1 and L 2 Each is an arylene group that is independently a single bond or substituted or unsubstituted cyclic carbon group with 6 to 50 carbon atoms.

[0572] In one embodiment of the present invention, preferably, L 1 and L 2 One of them is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic ring, and the other one is a single bond.

[0573] In another aspect of the invention, L 1 and L 2 Preferably, each arylene group is independently substituted or unsubstituted, and has 6 to 50 cyclic carbon atoms.

[0574] In another embodiment of the invention, L 1 and L 2 Single bonds are preferred.

[0575] L 1 and L 2 Details of the substituted or unsubstituted arylene groups with carbon numbers of 6 to 50 are indicated with respect to L. 3 and L 4 The details of the described aryl groups are the same.

[0576] L 1 and L2 The unsubstituted or unsubstituted arylene group representing a cyclic carbon number of 6 to 50 is preferably selected independently from phenylene, biphenylene, naphthylene, and phenanthrene.

[0577] Cz is a group represented by formula (1-a) or formula (1-b) below.

[0578] [Chemical Formula 27]

[0579]

[0580] R 21 ~R 28 and R 31 ~R 38 Each can be a hydrogen atom or a substituent independently.

[0581] The substituent is selected from substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic groups with 5 to 50 carbon atoms, substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms, fluorine atoms, and cyano groups.

[0582] Preferably, the atom is selected from hydrogen atoms, substituted or unsubstituted aryl groups having 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic groups having 5 to 50 carbon atoms, and substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, and more preferably hydrogen atoms.

[0583] Selected from R 21 ~R 28 One of them, preferably R 21 R 22 R 23 Or R 24 , more preferably R 23 For the purpose of connecting with L via *a 3 Bonded single bonds, *b indicates a bond with L 3 The location of the bond.

[0584] Not through *a and L 3 bonded single bond R 21 ~R 28 Both can be hydrogen atoms. Additionally, R... 31 ~R 38 Both can be hydrogen atoms.

[0585] Selected from L not via *a 3 bonded single bond R 21 ~R 28 The two adjacent ones in the middle, that is, selected from R 21 With R 22 R 22 With R 23 R 23With R 24 R 25 With R 26 R 26 With R 27 R 27 With R 28 At least one group of two adjacent rings can be bonded to each other to form a substituted or unsubstituted ring, or they can not be bonded to each other and thus not form a ring, preferably not bonded to each other and thus not form a ring.

[0586] Not through *a and L 3 bonded single bond R 24 With R 25 They can bond with each other to form substituted or unsubstituted rings, or they can not bond with each other and thus not form rings, preferably they do not bond with each other and thus not form rings.

[0587] Selected from R 31 ~R 38 The two adjacent ones in the middle, that is, selected from R 31 With R 32 R 32 With R 33 R 33 With R 34 R 35 With R 36 R 36 With R 37 R 37 With R 38 At least one group of two adjacent rings can be bonded to each other to form a substituted or unsubstituted ring, or they can not be bonded to each other and thus not form a ring, preferably not bonded to each other and thus not form a ring.

[0588] R 34 With R 35 They can bond with each other to form substituted or unsubstituted rings, or they can not bond with each other and thus not form rings, preferably they do not bond with each other and thus not form rings.

[0589] The details of the substituted or unsubstituted rings mentioned above are consistent with those for rings selected from R. 1 ~R 6 The records of at least one group of two adjacent, arbitrarily formed rings are identical.

[0590] Not through *a and L 3 bonded single bond R 21 ~R 28 and R 31 ~R 38The details of the substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, the substituted or unsubstituted heterocyclic groups with 5 to 50 carbon atoms, the substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, and the substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms are the same as those of the corresponding groups described above for R.

[0591] The aforementioned substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms are preferably groups that do not contain nitrogen-containing five-membered rings or nitrogen-containing seven-membered rings. Examples of heterocyclic groups containing nitrogen-containing five-membered rings include groups containing pyrrolidine, pyrrololine, pyrrole, carbazole, and similar structures. Examples of heterocyclic groups containing nitrogen-containing seven-membered rings include groups containing azepine, azepane, and similar structures.

[0592] In one aspect of the invention, it is preferred that the material is selected from those not derived from *a and L. 3 bonded single bond R 21 ~R 28 At least one of them, or selected from R 31 ~R 38 At least one of them is the above-mentioned substituent. The above-mentioned substituent is preferably cyano, substituted or unsubstituted aryl with 6 to 50 carbon atoms, or substituted or unsubstituted alkyl with 1 to 50 carbon atoms.

[0593] The unsubstituted aryl groups of the substituted or unsubstituted cyclic carbon groups with 6 to 50 carbon atoms are preferably each independently selected from phenyl, biphenyl, naphthyl, and phenanthrene.

[0594] The unsubstituted alkyl group of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms is preferably selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl.

[0595] R a It is an aryl group with 6 to 50 carbon atoms that is either substituted or unsubstituted, or an alkyl group with 1 to 50 carbon atoms that is either substituted or unsubstituted.

[0596] The details of the substituted or unsubstituted aryl groups having 6 to 50 carbon atoms, and the substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, are the same as the details of the corresponding groups described above for R.

[0597] R a The unsubstituted aryl group representing the substituted or unsubstituted cyclic carbon number of 6 to 50 is preferably selected from phenyl, biphenyl, naphthyl, and phenanthrene.

[0598] R aThe unsubstituted or unsubstituted alkyl group having 1 to 50 carbon atoms is preferably selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl.

[0599] In a preferred embodiment of the invention, compound A comprises the compound represented by formula (1-b-1) or (1-b-2).

[0600] [Chemical Formula 28]

[0601]

[0602] (in the formula,

[0603] Y 1 Y 2 Ar 1 Ar 2 L 1 L 2 and R 1 ~R 6 Same as the definition in equation (1),

[0604] R 31 ~R 38 Same as the definition in equation (1-b),

[0605] R 41 ~R 42 R 44 ~R 45 R 51 ~R 52 and R 54 ~R 55 Each is independently selected from hydrogen atoms, substituted or unsubstituted aryl groups having 6 to 50 carbon atoms in a cyclic ring, and substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms.

[0606] Selected from R 41 With R 42 R 44 With R 45 R 51 With R 52 and R 54 With R 55 At least one pair of adjacent benzene rings can bond to each other to form a substituted or unsubstituted benzene ring, or they can not bond to each other and therefore not form a benzene ring.

[0607] R 41 R 42 R 44 and R 45 Both can be hydrogen atoms. Additionally, R... 51 R 52 R 54 and R 55Both can be hydrogen atoms.

[0608] R 41 ~R 42 R 44 ~R 45 R 51 ~R 52 and R 54 ~R 55 The details of the substituted or unsubstituted aryl groups with 6 to 50 carbon atoms and the substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms are the same as those of the corresponding groups described above for R.

[0609] In one embodiment of the invention, it is preferably selected from R 41 With R 42 and R 44 With R 45 At least one set of two adjacent benzene rings are bonded together to form a substituted or unsubstituted benzene ring. In another aspect of the invention, it is preferable not to form the aforementioned benzene ring.

[0610] In one embodiment of the invention, it is preferably selected from R 51 With R 52 and R 54 With R 55 At least one set of two adjacent benzene rings are bonded together to form a substituted or unsubstituted benzene ring. In another aspect of the invention, it is preferable not to form the aforementioned benzene ring.

[0611] In a preferred embodiment of the present invention, compound A comprises any compound represented by formula (1-b-11) to (1-b-14).

[0612] [Chemical Formula 29]

[0613]

[0614] [Chemical Formula 30]

[0615]

[0616] [Chemical Formula 31]

[0617]

[0618] [Chemical Formula 32]

[0619]

[0620] (in the formula,

[0621] Y 1 Y 2 Ar 1 Ar 2 L1 L 2 and R 1 ~R 6 Same as the definition in equation (1),

[0622] R 31 ~R 38 Same as the definition in equation (1-b),

[0623] R 41 R 44 and R 45 Same as the definition in equation (1-b-1),

[0624] R 43 Selected from hydrogen atoms, substituted or unsubstituted aryl groups having 6 to 50 carbon atoms, and substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms.

[0625] R 43 The details of the substituted or unsubstituted aryl groups having 6 to 50 carbon atoms and the substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms are the same as those of the corresponding groups described above for R. 41 and R 43 ~R 45 All and selected from R 41 and R 43 ~R 45 Two or three of them can be hydrogen atoms.

[0626] In a preferred embodiment of the present invention, compound A comprises a compound represented by any one of the formulas (1-a-1) to (1-a-4).

[0627] [Chemical Formula 33]

[0628]

[0629] [Chemical Formula 34]

[0630]

[0631] [Chemical Formula 35]

[0632]

[0633] [Chemical Formula 36]

[0634]

[0635] (in the formula,

[0636] Y 1 Y 2 Ar 1 Ar 2L 1 L 2 and R 1 ~R 6 Same as the definition in equation (1),

[0637] R a and R 21 ~R 28 Same as the definition in equation (1-a),

[0638] R 41 ~R 42 and R 44 ~R 45 Same as the definition in equation (1-b-1).

[0639] As stated above, the term "hydrogen atom" as used in this specification includes protium, deuterium, and tritium atoms. Therefore, compound A may contain naturally occurring deuterium atoms.

[0640] Alternatively, a deuterium atom can be intentionally introduced into compound A by using a deuterated compound in part or all of the raw material compound. Therefore, in one aspect of the invention, compound A contains at least one deuterium atom. That is, compound A can be a compound of formula (1) or a compound of the above formula contained in formula (1), wherein at least one of the hydrogen atoms contained in the compound is a deuterium atom.

[0641] In equation (1), the terms are selected from R and R 1 ~R 6 R is not a single bond that bonds with *a 21 ~R 28 and R 31 ~R 38 The hydrogen atom, R, R 1 ~R 6 R is not a single bond that bonds with *a 21 ~R 28 and R 31 ~R 38 The substituents represented have hydrogen atoms, L 1 L 2 L 3 and L 4 The arylene group represents the hydrogen atom, R a The aryl or alkyl group represents the hydrogen atom, Ar... 1 and Ar 2 The aryl or heterocyclic group may have at least one hydrogen atom among its hydrogen atoms, which may be a deuterium atom.

[0642] The deuteration rate (the ratio of the number of deuterium atoms in compound A to the total number of hydrogen atoms) of the deuterated compound A depends on the deuteration rate of the starting material compounds used. It is usually difficult to set the deuteration rate of all the starting material compounds used to 100%, so the deuteration rate of compound A is less than 100%, preferably 95% or less, more preferably 90% or less, and even more preferably 80% or less.

[0643] The deuteration rate of the deuterated compound A is 1% or more, preferably 3% or more, more preferably 5% or more, and even more preferably 10% or more.

[0644] Compound A may be a mixture comprising a deuterated compound (a compound with deuterium atoms intentionally introduced) and an undeuterated compound, or a mixture of two or more compounds with different deuteration rates. The deuteration rate (the ratio of the number of deuterium atoms in compound A contained in the mixture to the total number of hydrogen atoms) of such a mixture is 1% or more, preferably 3% or more, more preferably 5% or more, even more preferably 10% or more, and less than 100%.

[0645] In compound A, at least one hydrogen atom selected from the hydrogen atoms represented by R or the hydrogen atoms of the substituent represented by R can be a deuterium atom. The deuteration rate (the ratio of the number of deuterium atoms to the total number of hydrogen atoms of the hydrogen atoms represented by R or the total number of hydrogen atoms of the substituent represented by R) is 1% or more, preferably 3% or more, more preferably 5% or more, even more preferably 10% or more, and less than 100%.

[0646] In compound A, the compound is selected from R. 1 ~R 6 The hydrogen atom and R represent 1 ~R 6 The substituent indicated has at least one hydrogen atom, which can be a deuterium atom. Deuteration rate (number of deuterium atoms relative to R) 1 ~R 6 The hydrogen atom represented by R 1 ~R 6 The percentage of the total number of hydrogen atoms in the substituents is 1% or more, preferably 3% or more, more preferably 5% or more, and even more preferably 10% or more, and less than 100%.

[0647] In compound A, R is selected from single bonds that are not bonded to *a. 21 ~R 28 The hydrogen atom represented and the R atom not bonded to *a are not single bonds. 21 ~R 28 The substituent indicated has at least one hydrogen atom, which can be a deuterium atom. The deuteration rate (the number of deuterium atoms relative to the R of single bonds not bonded to *a) 21 ~R 28The hydrogen atom represented and the R atom not bonded to *a are not single bonds. 21 ~R 28 The percentage of the total number of hydrogen atoms in the substituents is 1% or more, preferably 3% or more, more preferably 5% or more, even more preferably 10% or more, and less than 100%, preferably 95% or less, more preferably 90% or less.

[0648] In compound A, the compound is selected from R. 31 ~R 38 The hydrogen atom and R represent 31 ~R 38 The substituent indicated has at least one hydrogen atom, which can be a deuterium atom. Deuteration rate (number of deuterium atoms relative to R) 31 ~R 38 The hydrogen atom and R represent 31 ~R 38 The percentage of the total number of hydrogen atoms in the substituents is 1% or more, preferably 3% or more, more preferably 5% or more, and even more preferably 10% or more, and less than 100%.

[0649] In compound A, the compound is selected from L 1 and L 2 The arylene group represents a group in which at least one hydrogen atom can be a deuterium atom. Deuteration rate (the number of deuterium atoms relative to L) 1 and L 2 The percentage of the total number of hydrogen atoms in the arylene group is 1% or more, preferably 3% or more, more preferably 5% or more, and even more preferably 10% or more, and less than 100%.

[0650] In compound A, the compound is selected from L 3 and L 4 The arylene group represents a group in which at least one hydrogen atom can be a deuterium atom. Deuteration rate (the number of deuterium atoms relative to L) 3 and L 4 The percentage of the total number of hydrogen atoms in the arylene group is 1% or more, preferably 3% or more, more preferably 5% or more, and even more preferably 10% or more, and less than 100%.

[0651] In compound A, the compound is selected from R. a The aryl group indicates that at least one of its hydrogen atoms can be a deuterium atom. Deuteration rate (the number of deuterium atoms relative to R) a The percentage of the total number of hydrogen atoms in the aryl or alkyl group is 1% or more, preferably 3% or more, more preferably 5% or more, and even more preferably 10% or more, and less than 100%.

[0652] In compound A, Ar is selected. 1 and Ar2 The aryl or heterocyclic group indicates that at least one hydrogen atom is a deuterium atom. Deuteration rate (number of deuterium atoms relative to Ar). 1 and Ar 2 The percentage of the total number of hydrogen atoms in the aryl or heterocyclic group is 1% or more, preferably 3% or more, more preferably 5% or more, and even more preferably 10% or more, and less than 100%.

[0653] In the case where each group of compound A has substituents, the optional substituents indicated by "substituted or unsubstituted" are each independently an aryl group having 6 to 50 carbon atoms, an alkyl group having 1 to 50 carbon atoms, or a cycloalkyl group having 3 to 50 carbon atoms.

[0654] The details of each optional substituent are the same as those for R in formula (1).

[0655] The molecular weight of compound A is preferably 650 or more, more preferably 650 to 5000, even more preferably 650 to 3000, and particularly preferably 650 to 2000. If the molecular weight is within this range, the performance of the organic EL element is improved.

[0656] Those skilled in the art can readily produce compound A by referring to the following synthetic examples and known synthetic methods.

[0657] The following examples illustrate, but are not limited to, compounds A.

[0658] In the specific examples below, D represents a deuterium atom.

[0659] [Chemical Formula 37]

[0660]

[0661] [Chemical Formula 38]

[0662]

[0663] [Chemical Formula 39]

[0664]

[0665] [Chemical Formula 40]

[0666]

[0667] [Chemical Formula 41]

[0668]

[0669] [Chemical Formula 42]

[0670]

[0671] [Chemical Formula 43]

[0672]

[0673] [Chemical Formula 44]

[0674]

[0675] [Chemical Formula 45]

[0676]

[0677] [Chemical Formula 46]

[0678]

[0679] [Chemical Formula 47]

[0680]

[0681] [Chemical Formula 48]

[0682]

[0683] [Chemical Formula 49]

[0684]

[0685] [Chemical Formula 50]

[0686]

[0687] [Chemical Formula 51]

[0688]

[0689] [Chemical Formula 52]

[0690]

[0691] [Chemical Formula 53]

[0692]

[0693] [Chemical Formula 54]

[0694]

[0695] [Chemical Formula 55]

[0696]

[0697] [Chemical Formula 56]

[0698]

[0699] [Chemical Formula 57]

[0700]

[0701] [Chemical Formula 58]

[0702]

[0703] [Chemical Formula 59]

[0704]

[0705] [Chemical Formula 60]

[0706]

[0707] [Chemical Formula 61]

[0708]

[0709] Main material B

[0710] The main material B is represented by formula (10) and is used for the light-emitting layer.

[0711] [Chemical Formula 62]

[0712]

[0713] R selected from equation (10) 101 ~R 110 At least one of them, preferably R 110 With R 109 Each is an independent group represented by formula (31).

[0714] When there are more than two groups represented by formula (31), the two or more groups represented by formula (31) can be the same or different.

[0715] -L 101 -Ar 101 (31)

[0716] L in equation (31) 101 for

[0717] single bond,

[0718] The substituted or unsubstituted arylene group having 6 to 50 cyclic carbon atoms, or the substituted or unsubstituted divalent heterocyclic group having 5 to 50 cyclic atoms, preferably a single bond or a substituted or unsubstituted arylene group having 6 to 50 cyclic carbon atoms;

[0719] Ar 101 for

[0720] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0721] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0722] R selected from groups not represented by formula (31) 101 ~R 110 One or more adjacent pairs in a ring can bond to each other to form a substituted or unsubstituted ring, or they can not bond to each other and therefore not form a ring.

[0723] R is not a group shown in formula (31) and does not form the above-mentioned ring. 101 ~R 110 Each of the following groups is independently composed of a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group with 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 50 carbon atoms, or a -Si(R group). 901 (R) 902 (R) 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 (R) 907 The cyclic group may be a substituted or unsubstituted aryl group with 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 carbon atoms; preferably a hydrogen atom, a substituted or unsubstituted aryl group with 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 carbon atoms; more preferably a substituted or unsubstituted aryl group with 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 carbon atoms.

[0724] R is not a group shown in formula (31) and does not form the above-mentioned ring. 101 ~R 110 Both can be hydrogen atoms.

[0725] R 901 ~R 907 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 cyclic atoms, preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 cyclic carbon atoms.

[0726] In R 901 ~R 907 In the case of two or more R, two or more R 901 ~R907 They can be the same or different.

[0727] In one embodiment of the invention, the main material B represented by formula (10) comprises the compound represented by formula (10-1).

[0728] [Chemical Formula 63]

[0729]

[0730] (where R is in the formula) 101 ~R 108 L 101 and Ar 101 Same as the definition in equation (10).

[0731] In another embodiment of the invention, the main material B represented by formula (10) comprises the compound represented by formula (10-2).

[0732] [Chemical Formula 64]

[0733]

[0734] (where R is in the formula) 101 R 103 ~R 108 L 101 and Ar 101 Same as the definition in equation (10).

[0735] In another embodiment of the invention, the main material B represented by formula (10) comprises the compound represented by formula (10-3).

[0736] [Chemical Formula 65]

[0737]

[0738] (in the formula,

[0739] R 101A ~R 108A Each is independently a hydrogen atom or a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure, R 101A ~R 108A Both can be hydrogen atoms;

[0740] L 101A It is a single bond or a substituted or unsubstituted cyclic aryl group with 6 to 50 carbon atoms, and 2 L atoms. 101A They can be the same or different;

[0741] Ar 101A For substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, 2 Ar atoms 101A They can be the same or different.

[0742] In another embodiment of the invention, the main material B represented by formula (10) comprises the compound represented by formula (10-4).

[0743] [Chemical Formula 66]

[0744]

[0745] (in the formula,

[0746] L 101 and Ar 101 Same as the definition in equation (10);

[0747] R 101A ~R 108A Each is independently a hydrogen atom or a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure, R 101A ~R 108A Both can be hydrogen atoms;

[0748] X 11 For O, S or N(R) 61 ), preferably O or S;

[0749] R 61 It is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 cyclic carbon atoms, preferably a substituted or unsubstituted aryl group having 6 to 50 cyclic carbon atoms;

[0750] R 62 ~R 69 One of them is connected to L via * 101 Bonded single bonds;

[0751] Selected from not related to L 101 bonded single bond R 62 ~R 69 At least one pair of adjacent rings in a ring may bond together to form a substituted or unsubstituted ring, or they may not bond together and thus not form a ring.

[0752] Not with L 101 R with bonded single bonds that do not form the aforementioned ring 62 ~R 69 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 50 carbon atoms, all of which can be hydrogen atoms.

[0753] In another aspect of the invention, the main material B represented by formula (10) comprises the compound represented by formula (10-4A).

[0754] [Chemical Formula 67]

[0755]

[0756] (in the formula,

[0757] L 101 and Ar 101 Same as the definition in equation (10);

[0758] R 101A ~R 108A Each is independently a hydrogen atom or a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure, R 101A ~R 108A Both can be hydrogen atoms;

[0759] X 11 For O, S or N(R) 61 ), preferably O or S;

[0760] R 61 It is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 cyclic carbon atoms, preferably a substituted or unsubstituted aryl group having 6 to 50 cyclic carbon atoms;

[0761] Selected from R 62A ~R 69A Two adjacent rings in group 1, as shown in the format (10-4A-1);

[0762] R selected from the ring shown in formula (10-4A-1) 62A ~R 69A One or more adjacent pairs in a group can bond with each other to form a substituted or unsubstituted ring, or they can not bond with each other and therefore not form a ring;

[0763] The rings not formed by formula (10-4A-1) and other substituted or unsubstituted rings described above are not R 62A ~R 69A Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 50 carbon atoms, all of which can be hydrogen atoms.

[0764] [Chemical Formula 68]

[0765]

[0766] (in the formula,

[0767] *1 and *2 are respectively selected from R 62A ~R 69A The two adjacent cyclic carbon atoms in the above group 1 are bonded together;

[0768] R 70~R 73 One of them is connected to L via * 101 Bonded single bonds;

[0769] Not with L 101 bonded single bond R 70 ~R 73 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 50 carbon atoms, all of which can be hydrogen atoms.

[0770] In another aspect of the invention, the main material B represented by formula (10) comprises the compound represented by formula (10-6).

[0771] [Chemical Formula 69]

[0772]

[0773] (in the formula,

[0774] L 101 and Ar 101 Same as the definition in equation (10),

[0775] R 101A ~R 108A Same as the definition in equation (10-4),

[0776] R 66 ~R 69 Same as the definition in equation (10-4),

[0777] X 12 (For O or S.)

[0778] In another aspect of the invention, the main material B represented by formula (10-6) comprises the compound represented by formula (10-6H).

[0779] [Chemical Formula 70]

[0780]

[0781] (in the formula,

[0782] L 101 and Ar 101 Same as the definition in equation (10);

[0783] R 66 ~R 69 Same as the definition in equation (10-4);

[0784] X 12 (For O or S.)

[0785] In another aspect of the invention, the main material B represented by formula (10-6) or (10-6H) comprises a compound represented by formula (10-6Ha).

[0786] [Chemical Formula 71]

[0787]

[0788] (in the formula,

[0789] L 101 and Ar 101 Same as the definition in equation (10);

[0790] X 12 (For O or S.)

[0791] In another aspect of the invention, the main material B represented by formula (10-6), (10-6H), or (10-6Ha) comprises a compound represented by formula (10-6Ha-1) or (10-6Ha-2).

[0792] [Chemical Formula 72]

[0793]

[0794] (in the formula,

[0795] L 101 and Ar 101 Same as the definition in equation (10);

[0796] X 12 (For O or S.)

[0797] In another embodiment of the invention, the main material B represented by formula (10) comprises the compound represented by formula (10-7).

[0798] [Chemical Formula 73]

[0799]

[0800] (in the formula,

[0801] L 101 and Ar 101 Same as the definition in equation (10),

[0802] R 101A ~R 108A Same as the definition in equation (10-4),

[0803] X 11 Same as the definition in equation (10-4),

[0804] R 62 ~R69 Same as the definition in equation (10-4), where, selected from R 66 With R 67 R 67 With R 68 and R 68 With R 69 (One group consists of two adjacent rings that bond together to form substituted or unsubstituted rings.)

[0805] In another aspect of the invention, the main material B represented by formula (10) comprises the compound represented by formula (10-7H).

[0806] [Chemical Formula 74]

[0807]

[0808] (in the formula,

[0809] L 101 and Ar 101 Same as the definition in equation (10);

[0810] X 11 Same as the definition in equation (10-4);

[0811] R 62 ~R 69 Same as the definition in equation (10-4), where, selected from R 66 With R 67 R 67 With R 68 and R 68 With R 69 (One group consists of two adjacent rings that bond together to form substituted or unsubstituted rings.)

[0812] In another aspect of the invention, the main material B represented by formula (10) comprises the compound represented by formula (10-8).

[0813] [Chemical Formula 75]

[0814]

[0815] (in the formula,

[0816] L 101 and Ar 101 Same as the definition in equation (10),

[0817] R 101A ~R 108A Same as the definition in equation (10-4),

[0818] X 12 For O or S,

[0819] R 66 ~R 69 Same as the definition in equation (10-4), where, selected from R 66 With R 67 R 67 With R 68 and R 68 With R 69 (At least one set of two adjacent rings in the ring are bonded together to form a substituted or unsubstituted ring.)

[0820] In another aspect of the invention, the main material B represented by formula (10-8) comprises the compound represented by formula (10-8H).

[0821] [Chemical Formula 76]

[0822]

[0823] (in the formula,

[0824] L 101 and Ar 101 Same as the definition in equation (10);

[0825] R 66 ~R 69 Same as the definition in equation (10-4), where, selected from R 66 With R 67 R 67 With R 68 and R 68 With R 69 Two adjacent rings in one group are bonded to each other to form a substituted or unsubstituted ring, preferably an unsubstituted benzene ring;

[0826] X 12 (For O or S.)

[0827] In another aspect of the invention, formulas (10-7), (10-7H), (10-8), or (10-8H) are selected from R. 66 With R 67 R 67 With R 68 and R 68 With R 69 In a given group, two adjacent bonds in a ring form a ring as shown in formula (10-8-1) or (10-8-2), while R does not form a ring as shown in formula (10-8-1) or (10-8-2). 66 ~R 69 It does not form a ring.

[0828] [Chemical Formula 77]

[0829]

[0830] (in the formula,

[0831] The two asterisks are respectively selected from R 66 With R 67 R 67 With R 68 and R 68 With R 69 The two adjacent cyclic carbon atoms in the above group 1 are bonded together;

[0832] R 80 ~R 83 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 50 carbon atoms, R 80 ~R 83 Both can be hydrogen atoms;

[0833] X 13 (For O or S.)

[0834] In another embodiment of the invention, the main material B represented by formula (10) comprises the compound represented by formula (10-9).

[0835] [Chemical Formula 78]

[0836]

[0837] (in the formula,

[0838] L 101 and Ar 101 Same as the definition in equation (10),

[0839] R 101A ~R 108A Same as the definition in equation (10-4),

[0840] R 66 ~R 69 Same as the definition in equation (10-4), where, selected from R 66 With R 67 R 67 With R 68 and R 68 With R 69 Two adjacent elements in the structure do not bond to each other and therefore do not form a ring.

[0841] X 12 (For O or S.)

[0842] In another aspect of the invention, the main material B represented by formula (10) comprises compounds represented by formulas (10-10-1) to (10-10-4).

[0843] [Chemical Formula 79]

[0844]

[0845] [Chemical Formula 80]

[0846]

[0847] [Chemical Formula 81]

[0848]

[0849] [Chemical Formula 82]

[0850]

[0851] (where L) 101A Ar 101A and R 101A ~R 108A Same as the definition in equation (10-3).

[0852] In another aspect of the invention, the main material B represented by formulas (10-10-1) to (10-10-4) comprises compounds represented by formulas (10-10-1H) to (10-10-4H).

[0853] [Chemical Formula 83]

[0854]

[0855] [Chemical Formula 84]

[0856]

[0857] [Chemical Formula 85]

[0858]

[0859] [Chemical Formula 86]

[0860]

[0861] (where L) 101A and Ar 101A Same as the definition in equation (10-3).

[0862] Unless otherwise specified, the details of the two adjacent formed rings contained in formula (10) representing the main material B and other formulas are the same as those described for the two adjacent formed rings in formula (1), preferably benzene rings, benzofuran rings, or benzothiophene rings.

[0863] The details of each substituent contained in formula (10) representing the main material B and other formulas are the same as those described in the column [Substituents described in this specification].

[0864] In formula (10) representing the main material B and other formulas, the halogen atom is preferably a fluorine atom.

[0865] In formula (10) representing the main material B and other formulas, the unsubstituted alkyl group of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, more preferably methyl, isopropyl or tert-butyl.

[0866] In formula (10) representing the main material B and other formulas, the unsubstituted alkenyl group of the substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms is preferably vinyl or allyl.

[0867] In formula (10) representing the main material B and other formulas, the unsubstituted alkynyl group of the substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms is preferably acetylenyl.

[0868] In formula (10) representing the main material B and other formulas, the unsubstituted or unsubstituted cycloalkyl group of the cycloalkyl group having 3 to 50 carbon atoms is preferably cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, more preferably cyclopropyl, cyclopentyl or cyclohexyl.

[0869] In equation (10) representing the main material B, and in other equations, -Si(R 901 (R) 902 (R) 903 The silane is a monosubstituted silane, a disubstituted silane, or a trisubstituted silane, preferably a trisubstituted silane, more preferably a trimethylsilane, triethylsilane, tert-butyldimethylsilane, propyldimethylsilane, isopropyldimethylsilane, triphenylsilane, phenyldimethylsilane, tert-butyldiphenylsilane, or tricrylsilane.

[0870] In equation (10) representing the main material B, and in other equations, -O-(R 904 The alkoxy group is substituted or unsubstituted, or substituted or unsubstituted, aryloxy group, preferably methoxy, ethoxy, isopropoxy, sec-propoxy, tert-butoxy, phenoxy, or biphenyloxy.

[0871] In equation (10) representing the main material B, and in other equations, -S-(R 905 The group is a substituted or unsubstituted alkylthio group or a substituted or unsubstituted arylthio group, preferably methylthio, ethylthio, isopropylthio, sec-propylthio, tert-butylthio, phenylthio, or biphenylthio.

[0872] In equation (10) representing the main material B, and in other equations, -N(R 906 (R) 907 The amino group is a monosubstituted amino group or a disubstituted amino group, preferably a disubstituted amino group, and more preferably a dimethylamino group, a diethylamino group, a diisopropylamino group, or a diphenylamino group.

[0873] In formula (10) representing the main material B and other formulas, the substituted or unsubstituted aryl group with 6 to 50 carbon atoms is preferably phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, benzo[a]phenanthrene, pyrene, phenylenetriethylene, benzo[a]triethylene, 9,9-dimethylfluorenyl, benzo[a]-9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl or 9,9'-spirobisfluorenyl.

[0874] In formula (10) representing the main material B and other formulas, the heterocyclic group with 5 to 50 cyclic atoms, whether substituted or unsubstituted, is preferably pyridyl, pyrimidinyl, triazine, dibenzofuranyl, benzodibenzofuranyl, benzofuran-dibenzofuranyl, dibenzothiophenyl, benzodibenzothiophenyl, 9-carbazoyl or 9-phenylcarbazoyl.

[0875] In formula (10) representing the main material B and other formulas, the substituted or unsubstituted arylene group with 6 to 50 carbon atoms is preferably phenylene (o-phenylene, m-phenylene, p-phenylene), naphthylene (1,3-naphthylene, 1,4-naphthylene, 2,6-naphthylene), anthracene (9,10-anthraylene), or 9,9-dimethylfluorene-2,7-diyl.

[0876] In formula (10) representing the host material B and other formulas, the unsubstituted or unsubstituted divalent heterocyclic group with a cyclic atom number of 5 to 50 is preferably a divalent residue of an aromatic heterocycle selected from pyridine, pyrimidine, triazine, carbazole, benzocarbazole, benzofuran, dibenzofuran, naphthobenzofuran, benzothiophene, and dibenzothiophene.

[0877] When the groups of the main material B have substituents, the optional substituents indicated by "substituted or unsubstituted" are each independently an aryl group having 6 to 50 carbon atoms, an alkyl group having 1 to 50 carbon atoms, or a cycloalkyl group having 3 to 50 carbon atoms.

[0878] The details of each optional group are the same as those for R in formula (1).

[0879] Similar to compound A, host material B may contain naturally derived deuterium atoms. Alternatively, deuterium atoms may be intentionally introduced into host material B by using a deuterated compound in part or all of the starting material compound. Therefore, in one embodiment of the invention, host material B contains at least one deuterium atom. That is, host material B may be a compound of formula (10) or a compound of the above formula contained in formula (10), wherein at least one of the hydrogen atoms contained in the compound is a deuterium atom.

[0880] In formula (10), R is selected from groups not shown in formula (31). 101 ~R 110 The group consisting of one or more adjacent optional rings having hydrogen atoms; R is not a group shown in formula (31) and does not form the above-mentioned ring. 101 ~R 110 The hydrogen atom represented; not the group shown in formula (31) and not forming the above-mentioned ring R 101 ~R 110 The substituents represented have hydrogen atoms; L in formula (31) 101 The arylene or heterocyclic group represented by the hydrogen atom; and the Ar of formula (31) 101 The aryl or heterocyclic group may contain at least one hydrogen atom selected from its hydrogen atoms, which may be a deuterium atom.

[0881] The deuteration rate (the ratio of deuterium atoms to total hydrogen atoms in the host material B) depends on the deuteration rate of the raw material compounds used. It is usually difficult to set the deuteration rate of all the raw material compounds used to 100%, so the deuteration rate of the host material B is less than 100%, preferably 95% or less, more preferably 90% or less, and even more preferably 80% or less.

[0882] The deuteration rate of the deuterated host material B is 1% or more, preferably 3% or more, more preferably 5% or more, and even more preferably 10% or more.

[0883] The host material B may be a mixture comprising a deuterated compound (a compound with deuterium atoms intentionally introduced) and an undeuterated compound, or a mixture of two or more compounds with different deuteration rates. The deuteration rate (the ratio of the number of deuterium atoms in the host material B contained in the mixture to the total number of hydrogen atoms) of such a mixture is 1% or more, preferably 3% or more, more preferably 5% or more, even more preferably 10% or more, and less than 100%.

[0884] In the host material B shown in formula (10), R is selected from groups not shown in formula (31). 101 ~R 110At least one hydrogen atom selected from the hydrogen atoms in one or more adjacent optionally formed rings may be a deuterium atom. The deuteration rate (the ratio of the number of deuterium atoms in the optionally formed rings to the total number of hydrogen atoms) is 1% or more, preferably 3% or more, more preferably 5% or more, even more preferably 10% or more, and less than 100%.

[0885] In the host material B shown in formula (10), R is selected from groups not shown in formula (31) and does not form the aforementioned ring. 101 ~R 110 The hydrogen atom represented and the R group which is not shown in formula (31) and does not form the above-mentioned ring are represented by the R group. 101 ~R 110 The substituent represented may have at least one hydrogen atom, which can be a deuterium atom. The deuteration rate (the number of deuterium atoms relative to the group not represented by formula (31) and not forming the aforementioned ring) is R. 101 ~R 110 The hydrogen atom represented and the R group which is not shown in formula (31) and does not form the above-mentioned ring are represented by the R group. 101 ~R 110 The percentage of the total number of hydrogen atoms in the substituents is 1% or more, preferably 3% or more, more preferably 5% or more, and even more preferably 10% or more, and less than 100%.

[0886] In the main material B shown in equation (10), L is selected from equation (31). 101 The arylene or heterocyclic group represented has at least one hydrogen atom, which can be a deuterium atom. Deuteration rate (L) 101 The ratio of the number of deuterium atoms in the arylene or heterocyclic group to the total number of hydrogen atoms is 1% or more, preferably 3% or more, more preferably 5% or more, and even more preferably 10% or more, and less than 100%.

[0887] In the main material B shown in equation (10), Ar selected from equation (31) 101 The aryl or heterocyclic group represented has at least one hydrogen atom, which can be a deuterium atom. Deuteration rate (Ar) 101 The percentage of deuterium atoms in the aryl or heterocyclic group relative to the total number of hydrogen atoms is 1% or more, preferably 3% or more, more preferably 5% or more, and even more preferably 10% or more, and less than 100%.

[0888] The main material B is a known compound that can be easily manufactured by referring to known synthesis methods.

[0889] The following are specific examples of main material B, but are not limited to the following compounds.

[0890] [Chemical Formula 87]

[0891]

[0892] [Chemical Formula 88]

[0893]

[0894] [Chemical Formula 89]

[0895]

[0896] [Chemical Formula 90]

[0897]

[0898] [Chemical Formula 91]

[0899]

[0900] [Chemical Formula 92]

[0901]

[0902] [Chemical Formula 93]

[0903]

[0904] [Chemical Formula 94]

[0905]

[0906] [Chemical Formula 95]

[0907]

[0908] [Chemical Formula 96]

[0909]

[0910] [Chemical Formula 97]

[0911]

[0912] [Chemical Formula 98]

[0913]

[0914] [Chemical Formula 99]

[0915]

[0916] [Chemical Formula 100]

[0917]

[0918] [Chemical Formula 101]

[0919]

[0920] [Chemical Formula 102]

[0921]

[0922] [Chemical Formula 103]

[0923]

[0924] [Chemical Formula 104]

[0925]

[0926] [Chemical Formula 105]

[0927]

[0928] [Chemical Formula 106]

[0929]

[0930] [Chemical Formula 107]

[0931]

[0932] [Chemical Formula 108]

[0933]

[0934] [Chemical Formula 109]

[0935]

[0936] [Chemical Formula 110]

[0937]

[0938] [Chemical Formula 111]

[0939]

[0940] [Chemical Formula 112]

[0941]

[0942] [Chemical Formula 113]

[0943]

[0944] Organic EL components

[0945] The organic EL element of the present invention includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer includes an electron transport layer and a light-emitting layer, wherein the electron transport layer includes compound A and the light-emitting layer includes a host material B.

[0946] The organic EL element of the present invention can be a monochromatic light-emitting element of the fluorescent or phosphorescent type, or a white light-emitting element of the fluorescent / phosphorescent hybrid type. It can be a simple element with a single light-emitting unit, or a series-connected element with multiple light-emitting units. Here, "light-emitting unit" refers to the smallest unit that contains an organic layer, at least one of which is a light-emitting layer, and emits light by recombination of injected holes and electrons.

[0947] For example, the following are typical component configurations for a simple organic EL element.

[0948] (1) Anode / Light-emitting unit / Cathode

[0949] Alternatively, the aforementioned light-emitting unit can also be a multilayer type with multiple phosphorescent and fluorescent light-emitting layers. In this case, spacer layers can be provided between the light-emitting layers to prevent excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer. The following shows a typical layer configuration of a simplified light-emitting unit. The layers in parentheses are optional.

[0950] (a)(hole injection layer / )hole transport layer / fluorescent layer / electron transport layer( / electron injection layer)

[0951] (b) (Hole injection layer / ) Hole transport layer / phosphorescent layer / electron transport layer ( / electron injection layer)

[0952] (c)(hole injection layer / )hole transport layer / first fluorescent layer / second fluorescent layer / electron transport layer( / electron injection layer)

[0953] (d)(Hole Injection Layer / )Hole Transport Layer / First Phosphorescent Layer / Second Phosphorescent Layer / Electron Transport Layer( / Electron Injection Layer)

[0954] (e)(hole injection layer / )hole transport layer / phosphorescent layer / spacer layer / fluorescent layer / electron transport layer( / electron injection layer)

[0955] (f)(Hole injection layer / )Hole transport layer / First phosphorescent layer / Second phosphorescent layer / Spacer layer / Fluorescent layer / Electron transport layer( / Electron injection layer)

[0956] (g)(hole injection layer / )hole transport layer / first phosphorescent layer / spacer layer / second phosphorescent layer / spacer layer / fluorescent layer / electron transport layer ( / electron injection layer)

[0957] (h)(hole injection layer / )hole transport layer / phosphorescent layer / spacer layer / first fluorescent layer / second fluorescent layer / electron transport layer( / electron injection layer)

[0958] (i)(hole injection layer / )hole transport layer / electron blocking layer / fluorescent layer / electron transport layer( / electron injection layer)

[0959] (j)(hole injection layer / )hole transport layer / electron blocking layer / phosphorescent layer / electron transport layer( / electron injection layer)

[0960] (k)(hole injection layer / )hole transport layer / exciton blocking layer / fluorescent layer / electron transport layer( / electron injection layer)

[0961] (1)(Hole injection layer / )Hole transport layer / Exciton blocking layer / Phosphorescent layer / Electron transport layer( / Electron injection layer)

[0962] (m)(hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent layer / electron transport layer( / electron injection layer)

[0963] (n)(hole injection layer / )first hole transport layer / second hole transport layer / phosphorescent layer / electron transport layer( / electron injection layer)

[0964] (o)(hole injection layer / ) 1st hole transport layer / 2nd hole transport layer / fluorescent emission layer / 1st electron transport layer / 2nd electron transport layer ( / electron injection layer)

[0965] (p)(Hole Injection Layer / )First Hole Transport Layer / Second Hole Transport Layer / Phosphorescent Layer / First Electron Transport Layer / Second Electron Transport Layer( / Electron Injection Layer)

[0966] (q)(hole injection layer / )hole transport layer / fluorescent layer / hole blocking layer / electron transport layer( / electron injection layer)

[0967] (r)(hole injection layer / )hole transport layer / phosphorescent layer / hole blocking layer / electron transport layer( / electron injection layer)

[0968] (s)(hole injection layer / )hole transport layer / fluorescent layer / exciton blocking layer / electron transport layer( / electron injection layer)

[0969] (t)(hole injection layer / )hole transport layer / phosphorescent layer / exciton blocking layer / electron transport layer( / electron injection layer)

[0970] (u)(hole injection layer / )hole transport layer / electron blocking layer / phosphorescent layer / hole blocking layer / electron transport layer( / electron injection layer)

[0971] (v)(hole injection layer / )hole transport layer / electron blocking layer / fluorescent layer / hole blocking layer / electron transport layer( / electron injection layer)

[0972] Each of the aforementioned phosphorescent or fluorescent emitting layers can be configured to display a different emitting color. Specifically, in the aforementioned emitting unit (f), a layer configuration such as (hole injection layer / ) hole transport layer / first phosphorescent emitting layer (red emitting light) / second phosphorescent emitting layer (green emitting light) / spacer layer / fluorescent emitting layer (blue emitting light) / electron transport layer can be used.

[0973] It should be noted that electron blocking layers can be appropriately placed between each light-emitting layer and the hole transport layer or spacer layer. Similarly, hole blocking layers can be appropriately placed between each light-emitting layer and the electron transport layer. By placing electron blocking layers and hole blocking layers, electrons or holes can be confined within the light-emitting layer, thereby increasing the recombination probability of charges in the light-emitting layer and thus improving luminous efficiency.

[0974] The following are typical component configurations for tandem organic EL elements.

[0975] (2) Anode / First Light-Emitting Unit / Intermediate Layer / Second Light-Emitting Unit / Cathode

[0976] Here, the first light-emitting unit and the second light-emitting unit described above can be selected independently from the light-emitting units described above.

[0977] The aforementioned intermediate layer is also commonly referred to as an intermediate electrode, intermediate conductive layer, charge generation layer, electron extraction layer, connecting layer, or intermediate insulating layer, and can be constructed using known materials that supply electrons to the first light-emitting unit and holes to the second light-emitting unit.

[0978] Figure 1 This is a schematic diagram illustrating an example of the structure of the organic EL element of the present invention. The organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 10 disposed between the anode 3 and the cathode 4. The light-emitting unit 10 has a light-emitting layer 5. A hole transport region 6 (hole injection layer, hole transport layer, etc.) is provided between the light-emitting layer 5 and the anode 3, and an electron transport region 7 (electron injection layer, electron transport layer, etc.) is provided 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. As a result, electrons and holes can be confined in the light-emitting layer 5, thereby further improving the exciton generation efficiency in the light-emitting layer 5.

[0979] Figure 2This is a schematic diagram illustrating another configuration of the organic EL element of the present invention. The organic EL element 11 includes 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 hole injection layer 6a, a first hole transport layer 6b, and a second hole transport layer 6c. Furthermore, 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.

[0980] It should be noted that in this invention, the host material combined with a fluorescent dopant (fluorescent luminescent material) is called a fluorescent host material, and the host material combined with a phosphorescent dopant is called a phosphorescent host material. The distinction between fluorescent and phosphorescent hosts is not solely based on molecular structure. That is, a phosphorescent host material 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 to form a fluorescent luminescent layer. The same applies to fluorescent hosts.

[0981] substrate

[0982] The substrate serves as a support for the organic EL element. Examples of substrates include sheets made of glass, quartz, or plastic. Flexible substrates can also be used. Examples of flexible substrates include plastic substrates formed from polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. Inorganic vapor-deposited films can also be used.

[0983] anode

[0984] The anode formed on the substrate is preferably a metal, alloy, conductive compound, or mixture thereof with a high work function (specifically 4.0 eV or higher). Examples of such anodes include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. Other examples include 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 aforementioned metals (e.g., titanium nitride).

[0985] These materials are typically formed into films using sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1–10 wt% zinc oxide relative to indium oxide. Indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5–5 wt% tungsten oxide and 0.1–1 wt% zinc oxide relative to indium oxide. Alternatively, it can be fabricated using vacuum evaporation, coating, inkjet printing, spin coating, and other methods.

[0986] The hole injection layer formed adjacent to the anode is formed using a material that is easy to inject holes into regardless of the work function of the anode. Therefore, materials commonly used as electrode materials (e.g., metals, alloys, conductive compounds and mixtures thereof, elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0987] Elements belonging to Group 1 or Group 2 of the periodic table that have low work functions can also be used, namely alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them. It should be noted that when using alkali metals, alkaline earth metals, and their alloys to form the anode, vacuum evaporation or sputtering methods can be used. Furthermore, when using silver paste, coating or inkjet printing methods can be used.

[0988] Hole injection layer

[0989] A hole injection layer is a layer containing a material with high hole injection properties (hole injection material), which is formed between the anode and the light-emitting layer, or between the hole transport layer and the anode in the presence of a hole transport layer.

[0990] As hole-injection materials, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. can be used.

[0991] Examples of hole injection layer materials include 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), and 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (DNT). Aromatic amine compounds such as PD), 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), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1).

[0992] Polymers (oligomers, dendritic polymers, polymers, etc.) can also be used. Examples include: poly(N-vinylcarbazole) (PVK), poly(4-vinyltriphenylamine) (PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (Poly-TPD). Additionally, polymers containing acids, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

[0993] In addition, acceptor materials such as hexaazabenzophenanthrene (HAT) compounds represented by the following formula (K) are also preferred.

[0994] [Chemical Formula 114]

[0995]

[0996] (where R is in the formula) 21 ~R 26 Each can independently represent a cyano group, -CONH2, a carboxyl group, or -COOR. 27 (R 27 (Refers to alkyl groups having 1 to 20 carbon atoms or cycloalkyl groups having 3 to 20 carbon atoms). Additionally, it is selected from R... 21 and R 22 R 23 and R 24 and R 25 and R 26 Two adjacent groups can bond with each other to form a group represented by -CO-O-CO-.

[0997] As R 27 Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, and cyclohexyl.

[0998] Hole transport layer

[0999] A hole transport layer is a layer containing a material with high hole transport properties (hole transport material), which is formed between the anode and the light-emitting layer, or between the hole injection layer and the light-emitting layer in the presence of a hole injection layer.

[1000] The hole transport layer can be a single-layer structure or a multi-layer structure. For example, the hole transport layer can be a two-layer structure comprising a first hole transport layer (anode side) and a second hole transport layer (cathode side). In one embodiment of the 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 cathode in the multi-layer structure, such as the second hole transport layer in the two-layer structure, is preferably adjacent to the light-emitting layer. In another embodiment of the invention, an electron blocking layer, as described later, may be sandwiched between the hole transport layer and the light-emitting layer in the single-layer structure, or between the hole transport layer and the light-emitting layer closest to the light-emitting layer in the multi-layer structure.

[1001] As hole transport layer materials, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used, for example.

[1002] Examples of aromatic amine compounds include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BAFLP), and 4,4'-bis[N-(9,9-dimethylfluorene]... [N-(3-methylphenyl)-N-phenylamino]biphenyl (abbreviated as DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviated as TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as MTDATA), and 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB). The above compounds have 10 -6 cm 2 Hole mobility above / Vs.

[1003] Examples of carbazole derivatives include 4,4'-bis(9-carbazolyl)biphenyl (CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (PCzPA).

[1004] Examples of anthracene derivatives include 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (t-BuDNA), 9,10-bis(2-naphthyl)anthracene (DNA), and 9,10-diphenylanthracene (DPAnth).

[1005] Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) can also be used.

[1006] Among them, any compound whose hole transport capability is higher than that of electron transport capability can use compounds other than those mentioned above.

[1007] dopant material of the light-emitting layer

[1008] The luminescent layer is a layer containing a highly luminescent material (dopant material), and various materials can be used. For example, fluorescent luminescent materials and phosphorescent luminescent materials can be used as dopant materials. Fluorescent luminescent materials are compounds that emit light using a singlet excited state, while phosphorescent luminescent materials are compounds that emit light using a triplet excited state.

[1009] As blue fluorescent luminescent materials that can be used in the luminescent layer, pyrene derivatives, styrene amine derivatives, etc., can be used. Derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. Specifically, examples include N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviated as YGA2S), 4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthrayl)triphenylamine (abbreviated as YGAPA), and 4-(10-phenyl-9-anthrayl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCPAPA), etc.

[1010] As green fluorescent materials that can be used in the luminescent layer, aromatic amine derivatives can be used. Specifically, examples include N-(9,10-diphenyl-2-anthrayl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthrayl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCABPhA), and N-(9,10-diphenyl-2-anthrayl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPA). PA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthrayl]-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-phenylanthracene-2-amine (abbreviated as: 2YGABPhA), N,N,9-triphenylanthracene-9-amine (abbreviated as: DPhAPhA), etc.

[1011] As red-based fluorescent materials that can be used in the luminescent layer, tetraphenyl derivatives, diamine derivatives, etc., can be used. Specifically, examples include N,N,N',N'-tetra(4-methylphenyl)tetraphenyl-5,11-diamine (abbreviated as p-mPhTD) and 7,14-diphenyl-N,N,N',N'-tetra(4-methylphenyl)acenaphthene[1,2-a]fluoranthene-3,10-diamine (abbreviated as p-mPhAFD).

[1012] As blue phosphorescent materials that can be used in the luminescent layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes are employed. Specifically, examples include bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)tetra(1-pyrazolyl)borate (abbreviated as Fir6), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)pyridinecarboxylate (abbreviated as Firpic), bis[2-(3',5'-bistrifluoromethylphenyl)pyridine-N,C2']iridium(III)pyridinecarboxylate (abbreviated as Ir(CF3ppy)2(pic)), and bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)acetylacetone (abbreviated as FIracac).

[1013] As green phosphorescent materials that can be used in the luminescent layer, iridium complexes are used. Examples include 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)).

[1014] As red phosphorescent materials that can be used in the luminescent layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes can be used. Specifically, organometallic complexes such as bis[2-(2'-benzo[4,5-α]thienyl)pyridine-N,C3']iridium(III)acetylacetonate (abbreviated as: Ir(btp)2(acac)), bis(1-phenylisoquinoline-N,C2')iridium(III)acetylacetonate (abbreviated as: Ir(piq)2(acac)), (acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxaline]iridium(III) (abbreviated as: Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated as: PtOEP) can be used.

[1015] In addition, rare earth metal complexes such as tri(acetylacetonyl)(monophenanthrene)terbium(III) (abbreviated as Tb(acac)3(Phen)), tri(1,3-diphenyl-1,3-propanedione)(monophenanthrene)eupy(III) (abbreviated as Eu(DBM)3(Phen)), and tri[1-(2-thiophenecarboxyl)-3,3,3-trifluoroacetone](monophenanthrene)eupy(III) (abbreviated as Eu(TTA)3(Phen)) can be used as phosphorescent materials because their luminescence originates from the luminescence of rare earth metal ions (electronic transitions between different multiplicity levels).

[1016] The main material of the light-emitting layer

[1017] The light-emitting layer can be configured by dispersing the aforementioned dopant material within other materials (the host material). Preferably, a material with a lower unoccupied orbital level (LUMO level) higher than that of the dopant material and a higher occupied orbital level (HOMO level) lower than that of the dopant material is used.

[1018] In the organic EL element of the present invention, the above-mentioned host material B is used as the host material of the light-emitting layer.

[1019] In one embodiment of the present invention, the host material B contained in the luminescent layer comprises at least one deuterium atom. Alternatively, the host material B may be a mixture of a host material B (hereinafter referred to as "protium body") in which all hydrogen atoms are protium atoms and a host material B (deuterium body) in which at least one of all hydrogen atoms is a deuterium atom. The protium body may contain deuterium atoms in a proportion less than or equal to its natural abundance.

[1020] In one aspect of the present invention, the host material B contained in the light-emitting layer is preferably protium from the viewpoint of manufacturing cost. Therefore, the present invention includes an organic EL element in which the light-emitting layer comprises a host material B that is substantially composed solely of protium. "Host material B that is substantially composed solely of protium" means that, relative to the total amount of host material B, the proportion of protium is 90 mol% or more, preferably 95 mol% or more, and more preferably 99 mol% or more (each comprising 100%).

[1021] Besides the aforementioned main material B, other main materials can also be used. Examples of such other main materials include:

[1022] (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes;

[1023] (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives;

[1024] (3) Carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or Derivatives and other fused aromatic compounds,

[1025] (4) Aromatic amine compounds such as triarylamine derivatives or fused polycyclic aromatic amine derivatives.

[1026] For example, metal complexes such as tris(8-hydroxyquinoline)aluminum(III) (abbreviated as Alq), tris(4-methyl-8-hydroxyquinoline)aluminum(III) (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium(II) (abbreviated as BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviated as BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviated as ZnPBO), and bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviated as ZnBTZ) can be used;

[1027] Heterocyclic compounds such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), 3-(4-biphenyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviated as TAZ), 2,2',2”-(1,3,5-phenyltriyl)tris(1-phenyl-1H-benzimidazole) (abbreviated as TPBI), phenanthroline (abbreviated as BPhen), and copper bath (abbreviated as BCP);

[1028] 9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (abbreviated as CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (abbreviated as DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviated as DPPA), 9,10-bis(2-naphthyl)anthracene (abbreviated as DNA), 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (abbreviated as DNA) t-BuDNA), 9,9'-Bantane (BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (DPNS), 9,9'-(brusyl-4,4'-diyl)diphenanthrene (DPNS2), 3,3',3”-(benzene-1,3,5-triyl)tripyrene (TPB3), 9,10-diphenylanthracene (DPAnth), 6,12-dimethoxy-5,11-diphenyl Equally fused aromatic compounds; and

[1029] N,N-Diphenyl-9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthrayl)triphenylamine (abbreviation: DPhPA), N,9-Diphenyl-N-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), N,9-Diphenyl-N-{4-[4-(10-phenyl-9-anthrayl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthrayl)-N,9-diphenyl- Aromatic amine compounds such as 9H-carbazole-3-amine (abbreviated as 2PCAPA), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (abbreviated as DFLDPBi), and 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB).

[1030] Electron transport layer

[1031] An electron transport layer is a layer containing a material with high electron transport properties (electron transport material). It can be formed between the light-emitting layer and the cathode, or between the electron injection layer and the light-emitting layer in the presence of an electron injection layer.

[1032] The electron transport layer can be a single-layer structure or a multi-layer structure. For example, the electron transport layer can be a two-layer structure comprising a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one embodiment of the invention, the electron transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, or the electron transport layer closest to the anode in the multi-layer structure, such as the first electron transport layer in the two-layer structure, is preferably adjacent to the light-emitting layer. In another embodiment of the invention, a hole-blocking layer, as described later, may be sandwiched between the electron transport layer and the light-emitting layer in the single-layer structure, or between the electron transport layer closest to the light-emitting layer in the multi-layer structure.

[1033] The organic EL element of the present invention contains compound A in the electron transport layer.

[1034] In the electron transport layer of the above two-layer structure, compound A can be contained in one of the first electron transport layer and the second electron transport layer, or it can be contained in both.

[1035] In one embodiment of the invention, compound A is contained only in the first electron transport layer, and the second electron transport layer contains electron transport layer materials other than compound A.

[1036] In another embodiment, compound A is contained only in the second electron transport layer, while the first electron transport layer contains electron transport layer materials other than compound A.

[1037] In another embodiment, compound A is contained in both the first and second electron transport layers. One or both of the first and second electron transport layers may contain electron transport layer materials other than compound A.

[1038] In one embodiment of the invention, compound A contains at least one deuterium atom. Alternatively, compound A may be a mixture of compound A (hereinafter referred to as "protium body") in which all hydrogen atoms are protium atoms and compound A (deuterium body) in which at least one of all hydrogen atoms is a deuterium atom. The protium body may contain deuterium atoms in proportions below its natural abundance.

[1039] In one aspect of the present invention, from the viewpoint of manufacturing cost, the compound A contained in the electron transport layer (including the first electron transport layer and the second electron transport layer) is preferably protium.

[1040] Therefore, the present invention includes an organic EL element in which the electron transport layer comprises compound A, which is substantially composed of only protium. "Compound A, which is substantially composed of only protium" means that the proportion of protium in the total amount of compound A is 90 mol% or more, preferably 95 mol% or more, and more preferably 99 mol% or more (each comprising 100%).

[1041] Other electron transport layer materials besides compound A can be used. Examples of such other electron transport layer materials include:

[1042] (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes;

[1043] (2) Imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives, and other heteroaromatic compounds.

[1044] (3) Polymer compounds.

[1045] Examples of metal complexes include: tris(8-hydroxyquinoline)aluminum(III) (abbreviated as Alq), tris(4-methyl-8-hydroxyquinoline)aluminum (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium (abbreviated as BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviated as BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviated as ZnPBO), and bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviated as ZnBTZ).

[1046] Examples of heteroaromatic compounds include: 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (abbreviated as TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviated as p-EtTAZ), phenanthroline (abbreviated as BPhen), copper hydroxide (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviated as BzOs).

[1047] Examples of high molecular weight compounds include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy).

[1048] The above material has 10- 6 cm 2 Materials with electron mobility greater than / Vs. It should be noted that any material whose electron transport capability is higher than its hole transport capability can be used for the electron transport layer.

[1049] Electron injection layer

[1050] An electron injection layer is a layer containing materials with high electron injection capability. The electron injection layer can use alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), rare earth metals such as europium (Eu) and ytterbium (Yb), and compounds containing these metals. Examples of such compounds include alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes, alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, rare earth metal oxides, rare earth metal halides, and rare earth metal-containing organic complexes. Furthermore, multiple such compounds can be used in combination.

[1051] Furthermore, materials containing alkali metals, alkaline earth metals, or their compounds in an electron-transporting material can be used; specifically, materials containing magnesium (Mg) in Alq can be used. It should be noted that electron injection from the cathode can be performed more efficiently in this case.

[1052] Alternatively, the electron injection layer can be a composite material formed by mixing an organic compound with an electron donor. Such a composite material exhibits excellent electron injection and electron transport properties because the organic compound accepts electrons from the electron donor. In this case, the organic compound is preferably a material with excellent electron transport properties; specifically, materials constituting the electron transport layer, such as those described above (metal complexes, heteroaromatic compounds, etc.), can be used. The electron donor can be any material that exhibits electron-donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. Additionally, alkali metal oxides and alkaline earth metal oxides are preferred, such as lithium oxides, calcium oxides, and barium oxides. Furthermore, Lewis bases such as magnesium oxide can also be used. Additionally, organic compounds such as tetrathiofulvalene (TTF) can also be used.

[1053] cathode

[1054] The cathode preferably uses metals, alloys, conductive compounds, and mixtures thereof with low work functions (specifically, below 3.8 eV). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them.

[1055] It should be noted that when using alkali metals, alkaline earth metals, or alloys containing them to form the cathode, vacuum evaporation or sputtering methods can be used. Additionally, when using silver paste, coating or inkjet printing methods can be used.

[1056] It should be noted that by setting an electron injection layer, a wide variety of conductive materials, such as Al, Ag, ITO, graphene, and indium tin oxide containing silicon or silicon oxide, can be used to form cathodes regardless of the work function. These conductive materials can be deposited using methods such as sputtering, inkjet printing, and spin coating.

[1057] Insulation layer

[1058] Organic EL elements are prone to pixel defects due to leakage and short circuits because an electric field is applied to the ultrathin film. To prevent this, an insulating layer formed by an insulating thin film can be inserted between a pair of electrodes.

[1059] Examples of materials that can be used as insulating layers include alumina, 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 or laminates of these materials can also be used.

[1060] Spacer layer

[1061] In the case of a stacked fluorescent and phosphorescent layer, the spacer layer refers to a layer disposed between the fluorescent and phosphorescent layers to prevent excitons generated in the phosphorescent layer from diffusing to the fluorescent layer or to adjust carrier balance. Alternatively, the spacer layer may be disposed between multiple phosphorescent layers.

[1062] Since the spacer layer is disposed between the light-emitting layers, it is preferably made of a material that possesses both electron transport and hole transport properties. Furthermore, to prevent the diffusion of triplet energy within adjacent phosphorescent light-emitting layers, the triplet energy is preferably 2.6 eV or higher. Materials similar to those used for the hole transport layer can be cited as examples of materials for the spacer layer.

[1063] Barrier layer

[1064] Electron blocking layers, hole blocking layers, exciton blocking layers, and other blocking layers can also be placed adjacent to the light-emitting layer. An electron blocking layer prevents electrons from leaking from the light-emitting layer to the hole transport layer, while a hole blocking layer prevents holes from leaking from the light-emitting layer to the electron transport layer. An exciton blocking layer prevents excitons generated in the light-emitting layer from diffusing to surrounding layers, thus confining the excitons within the light-emitting layer.

[1065] The layers of the aforementioned organic EL element can be formed using conventional vapor deposition or coating methods. For example, they can be formed using vapor deposition methods such as vacuum vapor deposition or molecular beam vapor deposition (MBE), or known coating methods such as dip coating, spin coating, casting, rod coating, and roll coating, which utilize solutions of compounds forming the layers.

[1066] There are no particular restrictions on the thickness of each layer. Generally speaking, if the film thickness is too thin, defects such as pinholes are likely to occur. Conversely, if the film thickness is too thick, a high driving voltage is required and the efficiency will be reduced. Therefore, 5nm to 10μm is preferred, and 10nm to 0.2μm is more preferred.

[1067] The aforementioned organic EL elements can be used in display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, as well as electronic devices such as lighting and vehicle lamps.

[1068] Example

[1069] The present invention will be further described in detail below using examples, but the present invention is not limited to the following examples.

[1070] Compound A used in the manufacture of organic EL elements in Examples 1-38

[1071] [Chemical Formula 115]

[1072]

[1073] [Chemical Formula 116]

[1074]

[1075] [Chemical Formula 117]

[1076]

[1077] The comparative compounds used in the manufacture of organic EL elements in Comparative Examples 1 and 2

[1078] [Chemical Formula 118]

[1079]

[1080] Other compounds used in the manufacture of organic EL elements in Examples 1-21 and Comparative Example 1

[1081] [Chemical Formula 119]

[1082]

[1083] Other compounds used in the manufacture of organic EL elements in Examples 22-38 and Comparative Example 2

[1084] [Chemical Formula 120]

[1085]

[1086] The organic EL elements were fabricated as described below, and the EL element performance of each element was evaluated.

[1087] Example 1

[1088] Fabrication of organic EL components

[1089] A 25mm × 75mm × 1.1mm glass substrate (manufactured by Geomatec Corporation) with an ITO transparent electrode (anode) was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The ITO film thickness was set to 130nm.

[1090] A cleaned glass substrate with a transparent electrode was mounted on the substrate holder of a vacuum evaporation apparatus. First, compounds HT-1 and HI-1 were co-deposited on the side where the transparent electrode was formed, covering the transparent electrode, to form a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-1 to compound HI-1 was 97:3.

[1091] Next, compound HT-1 was deposited on the hole injection layer to form the first hole transport layer with a thickness of 80 nm.

[1092] Compound HT-2 was deposited on the hole transport layer to form a second hole transport layer with a thickness of 10 nm.

[1093] Next, compounds BH-1 (host material B) and BD-1 (dopant material) were co-deposited on the second hole transport layer to form a light-emitting layer with a thickness of 25 nm. The mass ratio of compound BH-1 to compound BD-1 was 96:4.

[1094] Next, compound Inv-1 was deposited on the light-emitting layer to form a first electron transport layer with a thickness of 10 nm.

[1095] A second electron transport layer with a thickness of 15 nm was formed by evaporating compound ET-1 onto the first electron transport layer.

[1096] An electron-injection electrode with a film thickness of 1 nm was formed by depositing Yb on the second electron transport layer.

[1097] Finally, metallic Al was deposited on the electron-injection electrode to form a metal cathode with a film thickness of 80 nm.

[1098] The following shows the layer structure of the organic EL element of Example 1. The numbers in parentheses are film thicknesses (nm), and the ratios are mass ratios.

[1099] ITO(130) / HT-1:HI-1=97:3(10) / HT-1(80) / HT-2(10) / BH-1:BD-1=96:4(25) / Compound Inv-1(10) / ET-1(15) / Yb(1) / Al(80)

[1100] Example 22

[1101] Fabrication of organic EL components

[1102] Similar to Example 1, a cleaned glass substrate with a transparent electrode was mounted on the substrate holder of a vacuum evaporation apparatus. First, compound HT-3 and compound HI-1 were co-deposited on the side where the transparent electrode was formed, covering the transparent electrode, to form a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-3 to compound HI-1 was 97:3.

[1103] Next, compound HT-3 was deposited on the hole injection layer to form the first hole transport layer with a thickness of 80 nm.

[1104] Compound HT-2 was deposited on the hole transport layer to form a second hole transport layer with a thickness of 5 nm.

[1105] Next, compound BH-2 (host material B) and compound BD-1 (dopant material) were co-deposited on the second hole transport layer to form a light-emitting layer with a thickness of 25 nm. The mass ratio of compound BH-2 to compound BD-1 was 96:4.

[1106] Next, compound Inv-1 was deposited on the light-emitting layer to form a first electron transport layer with a thickness of 5 nm.

[1107] Compound ET-2 and Liq were co-deposited on the first electron transport layer to form a second electron transport layer with a thickness of 20 nm. The mass ratio of compound ET-2 to Liq was 50:50.

[1108] An electron-injection electrode with a film thickness of 1 nm was formed by depositing Yb on the second electron transport layer.

[1109] Finally, metallic Al was deposited on the electron-injection electrode to form a metal cathode with a film thickness of 50 nm.

[1110] The following shows the layer structure of the organic EL element of Example 22. The numbers in parentheses are film thicknesses (nm), and the ratios are mass ratios.

[1111] ITO(130) / HT-3:HI-1=97:3(10) / HT-3(80) / HT-2(5) / BH-2:BD-1=96:4(25) / Compound Inv-1(5) / ET-2:Liq=50:50(20) / Yb(1) / Al(50)

[1112] Evaluation of organic EL devices

[1113] 95% lifespan (LT95)

[1114] The obtained organic EL element was subjected to a current density of 50 mA / cm². 2 A DC constant current drive was used, and the time it took for the brightness to decrease to 95% of the initial brightness was measured. This time was taken as the 95% lifetime (LT95). The results are shown in Table 1.

[1115] Examples 2-21 and Comparative Example 1

[1116] In Example 1, instead of compound Inv-1, compounds Inv-2 (Example 2), Inv-3 (Example 3), Inv-4 (Example 4), Inv-5 (Example 5), Inv-6 (Example 6), Inv-7 (Example 7), Inv-8 (Example 8), Inv9 (Example 9), Inv-10 (Example 10), Inv-11 (Example 11), Inv-12 (Example 12), Inv-13 (Example 13), Inv-14 (Example 14), Inv-15 (Example 15), Inv-16 (Example 16), Inv-17 (Example 17), Inv-18 (Example 18), Inv-19 (Example 19), Inv-20 (Example 20), Inv-21 (Example 21), or comparative compound Ref-1 (Comparative Example 1) were used to prepare EL elements in the same manner as in Example 1.

[1117] The 95% lifetime (LT95) of each organic EL element was determined in the same manner as in Example 1. The results are shown in Table 1.

[1118] Examples 23-38 and Comparative Example 2

[1119] In Example 22, instead of compound Inv-1, compounds Inv-2 (Example 23), Inv-3 (Example 24), Inv-5 (Example 25), Inv-6 (Example 26), Inv-8 (Example 27), Inv-9 (Example 28), Inv-10 (Example 29), Inv-11 (Example 30), Inv-12 (Example 31), Inv-13 (Example 32), Inv-14 (Example 33), Inv-15 (Example 34), Inv-17 (Example 35), Inv-18 (Example 36), Inv-20 (Example 37), Inv-21 (Example 38), or comparative compound Ref-1 (Comparative Example 2) were used to prepare each organic EL element in the same manner as in Example 22.

[1120] The 95% lifetime (LT95) of each organic EL element was determined in the same manner as in Example 22. The results are shown in Table 2.

[1121] [Table 1]

[1122] Table 1

[1123] First electron transport layer material LT95 (hours) Example 1 Compound Inv-1 38 Example 2 Compound Inv-2 44 Example 3 Compound Inv-3 69 Example 4 Compound Inv-4 62 Example 5 Compound Inv-5 65 Example 6 Compound Inv-6 58 Example 7 Compound Inv-7 38 Example 8 Compound Inv-8 82 Example 9 Compound Inv-9 49 Example 10 Compound Inv-10 46 Example 11 Compound Inv-11 48 Example 12 Compound Inv-12 66 Example 13 Compound Inv-13 55 Example 14 Compound Inv-14 45 Example 15 Compound Inv-15 56 Example 16 Compound Inv-16 60 Example 17 Compound Inv-17 85 Example 18 Compound Inv-18 60 Example 19 Compound Inv-19 65 Example 20 Compound Inv-20 70 Example 21 Compound Inv-21 45 Comparative Example 1 Comparison of compound Ref-1 34

[1124] [Table 2]

[1125] Table 2

[1126] First electron transport layer material LT95 (hours) Example 22 Compound Inv-1 159 Example 23 Compound Inv-2 158 Example 24 Compound Inv-3 248 Example 25 Compound Inv-5 211 Example 26 Compound Inv-6 140 Example 27 Compound Inv-8 250 Example 28 Compound Inv-9 176 Example 29 Compound Inv-10 165 Example 30 Compound Inv-11 174 Example 31 Compound Inv-12 190 Example 32 Compound Inv-13 260 Example 33 Compound Innv-14 172 Example 34 Compound Inv-15 173 Example 35 Compound Inv-17 192 Example 36 Compound Inv-18 160 Example 37 Compound Inv-20 250 Example 38 Compound Inv-21 160 Comparative Example 2 Comparison of compound Ref-1 135

[1127] According to the results in Table 1, compared to the organic EL element of Comparative Example 1, which contains the comparative compound Ref-1 in the first electron transport layer, the organic EL elements of Examples 1 to 21, which contain compounds Inv-1 to Inv-21 in the first electron transport layer respectively, have a longer lifetime.

[1128] According to the results in Table 2 (which includes changes to the main material B, and the other compounds used in the manufacture of the organic EL element are different; these are fixed in each example and comparative example), the organic EL elements of Examples 22 to 38, whose first electron transport layer contains the comparative compound Ref-1, have a longer lifetime than the organic EL element of Comparative Example 2, whose first electron transport layer contains compounds Inv-1 to Inv-3, Inv-5, Inv-6, Inv-8 to Inv-15, Inv-17, Inv-18, Inv-20, and Inv-21, respectively.

[1129] Compounds Inv-1 to Inv-21 synthesized in Synthetic Examples 1 to 7

[1130] [Chemical Formula 121]

[1131]

[1132] [Chemical Formula 122]

[1133]

[1134] [Chemical Formula 123]

[1135]

[1136] Synthesis Example 1: Synthesis of Compound Inv-1

[1137] (1-1) Synthesis of intermediate A

[1138] [Chemical Formula 124]

[1139]

[1140] 9.0 g of 4-bromo-1-naphthaldehyde, 4.6 g of acetophenone, and 0.15 g of sodium hydroxide were added to 300 mL of ethanol and stirred at room temperature for 5 hours. Next, 6.0 g of benzamide hydrochloride and 1.8 g of sodium hydroxide were added, and the mixture was stirred at 70 °C for 5 hours. After the reaction was complete, the precipitate was filtered off and purified by silica gel column chromatography (developing solvent: hexane / toluene) to obtain intermediate A as a white solid (7.6 g, yield 45%).

[1141] (1-2) Synthesis of compound Inv-1

[1142] [Chemical Formula 125]

[1143]

[1144] Intermediate A (3.6 g) and 4-(9H-carbazole-9-yl)phenylboronic acid (2.8 g) were added to 1,2-dimethoxyethane (80 mL), and argon gas was bubbled through the solution for 5 minutes. Pd(PPh3)4 (0.4 g) and an aqueous sodium carbonate solution (2 M, 12 mL) were then added, and the mixture was heated under reflux for 7 hours with stirring under an argon atmosphere. The solvent was distilled off from the reaction solution, and the resulting solid was purified by silica gel column chromatography (developing solvent: hexane / toluene) to give compound Inv-1 as a white solid (3.7 g, 75% yield).

[1145] The mass spectrometry analysis showed that, relative to a molecular weight of 599.74, the m / e ratio was 600, thus identifying it as compound Inv-1.

[1146] Synthesis Example 2: Synthesis of compound Inv-2

[1147] [Chemical Formula 126]

[1148]

[1149] Except for the use of intermediate A (5.0 g) and [4'-(carbazol-9-yl)-4-biphenyl]boronic acid (4.5 g), under the same conditions as in Synthesis Example 1 (1-2), compound Inv-2 was obtained as a white solid (6.6 g, yield 85%).

[1150] The mass spectrometry analysis showed that, relative to the molecular weight of 675.84, the m / e ratio was 676, thus identifying it as compound Inv-2.

[1151] Synthesis Example 3: Synthesis of compound Inv-3

[1152] (3-1) Synthesis of intermediate B

[1153] [Chemical Formula 127]

[1154]

[1155] 4-Bromo-1-naphthaldehyde (8.0 g), 4-acetylbiphenyl (7.0 g), and sodium hydroxide (0.27 g) were added to 600 mL of ethanol and stirred at room temperature for 5 hours. Next, benzamide hydrochloride (8.0 g) and sodium hydroxide (2.7 g) were added, and the mixture was stirred at 70 °C for 5 hours. After the reaction was complete, the precipitate was filtered off and purified by silica gel column chromatography (developing solvent: hexane / toluene) to give intermediate B as a white solid (5.0 g, yield 28%).

[1156] (3-2) Synthesis of compound Inv-3

[1157] [Chemical Formula 128]

[1158]

[1159] Except for the use of intermediate B (5.0 g), under the same conditions as in Synthesis Example 1 (1-2), compound Inv-3 was obtained as a white solid (4.5 g, yield 68%).

[1160] The mass spectrometry analysis showed that, relative to the molecular weight of 675.84, the m / e ratio was 676, thus identifying it as compound Inv-3.

[1161] Synthesis Example 4: Synthesis of compound Inv-4

[1162] (4-1) Synthesis of intermediate C

[1163] [Chemical Formula 129]

[1164]

[1165] Intermediate C was obtained as a white solid (9.0 g, yield 83%) under the same conditions as in Synthesis Example 1 (1-2), except that intermediate A (10.0 g) and 4-fluorophenylboronic acid (3.5 g) were used.

[1166] (4-2) Synthesis of compound Inv-4

[1167] [Chemical Formula 130]

[1168]

[1169] Intermediate C (3.8 g), 3,6-diphenylcarbazole (4.0 g), and cesium carbonate (8.2 g) were added to 30 mL of N-methylpyrrolidone (NMP), and the mixture was stirred at 160 °C for 24 hours. After cooling the reaction solution to room temperature, 100 mL of methanol and 100 mL of water were added, and the mixture was stirred at room temperature for 1 hour. The precipitated solid was filtered off and purified by silica gel column chromatography (developing solvent: hexane / toluene) to obtain compound Inv-4 as a white solid (6.3 g, yield 94%).

[1170] The mass spectrometry analysis showed that the m / e ratio was 752 relative to the molecular weight of 751.93, thus identifying it as compound Inv-4.

[1171] Synthesis Example 5: Synthesis of compound Inv-5

[1172] (5-1) Synthesis of intermediate D

[1173] [Chemical Formula 131]

[1174]

[1175] Except for the use of intermediate A (5.0 g) and 3,5-difluorophenylboronic acid (2.0 g), intermediate D was obtained as a white solid (4.2 g, yield 78%) under the same conditions as in synthesis example 1 (1-2).

[1176] (5-2) Synthesis of compound Inv-5

[1177] [Chemical Formula 132]

[1178]

[1179] Except for the use of intermediate D (4.2 g) and carbazole (4.5 g), under the same conditions as in synthesis example 4 (4-2), compound Inv-5 was obtained as a white solid (4.1 g, yield 60%).

[1180] The mass spectrometry analysis showed that, relative to the molecular weight of 764.93, the m / e ratio was 765, thus identifying it as compound Inv-5.

[1181] Synthesis Example 6: Synthesis of compound Inv-6

[1182] [Chemical Formula 133]

[1183]

[1184] Except for the use of intermediate A (3.9 g) and 9-phenyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborhecyclopentan-2-yl)phenyl]-9H-carbazole (4.0 g), under the same conditions as in Synthetic Examples 1 (1-2), compound Inv-6 was obtained as a white solid (4.7 g, yield 78%).

[1185] The mass spectrometry analysis showed that, relative to the molecular weight of 675.84, the m / e ratio was 676, thus identifying it as compound Inv-6.

[1186] Synthesis Example 7: Synthesis of compound Inv-7

[1187] [Chemical Formula 134]

[1188]

[1189] Except for the use of intermediate A (7.0 g) and 3-(9H-carbazole-9-yl)phenylboronic acid (5.1 g), under the same conditions as in Synthesis Example 1 (1-2), compound Inv-7 was obtained as a white solid (7.0 g, yield 73%).

[1190] The mass spectrometry analysis showed that, relative to a molecular weight of 599.74, the m / e ratio was 600, thus identifying it as compound Inv-7.

[1191] Synthesis Example 8: Synthesis of compound Inv-8

[1192] [Chemical Formula 135]

[1193]

[1194] Intermediate A (6.0 g), 3,6-diphenylcarbazole (4.2 g), palladium acetate (0.48 g), Amphos (1.3 g), and t-BuONa (3.8 g) were added to 168 mL of dehydrated xylene, and the mixture was stirred under reflux for 36 hours. After cooling the reaction solution to room temperature, 100 mL of methanol and 100 mL of water were added, and the mixture was stirred at room temperature for 1 hour. The precipitated solid was collected by filtration and purified by silica gel column chromatography (developing solvent: hexane / toluene) to give compound Inv-8 as a white solid (4.8 g, yield 52%).

[1195] The mass spectrometry analysis showed that, relative to the molecular weight of 675.84, the m / e ratio was 675, thus identifying it as compound Inv-8.

[1196] Synthesis Example 9: Synthesis of compound Inv-9

[1197] [Chemical Formula 136]

[1198]

[1199] Using intermediate C (5.6 g), under the same conditions as described in (4-2) of synthesis example 4, compound Inv-9 was obtained as a white solid (5.9 g, yield 61%).

[1200] The mass spectrometry analysis showed that the m / e ratio was 675 relative to the molecular weight of 675.84, thus identifying it as compound Inv-9.

[1201] Synthesis Example 10: Synthesis of compound Inv-10

[1202] [Chemical Formula 137]

[1203]

[1204] Using intermediate E (8.0 g) synthesized from 3-acetylbiphenyl as a starting material according to the method of (3-1) of Synthesis Example 3, under the same conditions as described in Synthesis Example 1, compound Inv-10 was obtained as a white solid (10.3 g, yield 87%).

[1205] The mass spectrometry analysis showed that the m / e ratio was 675 relative to the molecular weight of 675.84, thus identifying it as compound Inv-10.

[1206] Synthesis Example 11: Synthesis of compound Inv-11

[1207] [Chemical Formula 138]

[1208]

[1209] Using intermediates E (5.0 g) and F (3.6 g), under the same conditions as described in Synthesis Example 1, compound Inv-11 was obtained as a white solid (5.7 g, yield 78%).

[1210] The mass spectrometry analysis showed that the m / e ratio was 751 relative to the molecular weight of 751.93, thus identifying it as compound Inv-11.

[1211] Synthesis Example 12: Synthesis of compound Inv-12

[1212] [Chemical Formula 139]

[1213]

[1214] Using intermediate B (4.0 g) and intermediate F (2.8 g), under the same conditions as described in Synthesis Example 1, compound Inv-12 was obtained as a white solid (5.1 g, yield 87%).

[1215] The mass spectrometry analysis showed that the molecular weight was 751.93 and the m / e ratio was 751, thus identifying it as compound Inv-12.

[1216] Synthesis Example 13: Synthesis of compound Inv-13

[1217] (13-1) Synthesis of intermediate G

[1218] [Chemical Formula 140]

[1219]

[1220] Using intermediate A (10.0 g) and 4-chlorophenylboronic acid (3.6 g), under the same conditions as described in Synthesis Example 1, intermediate G was obtained as a white solid (9.8 g, yield 91%).

[1221] (13-2) Synthesis of compound Inv-13

[1222] [Chemical Formula 141]

[1223]

[1224] Intermediate G (4.5 g), N-phenylcarbazole-2-boric acid (4.1 g), and tripotassium phosphate (8.2 g) were added to 1,4-dioxane (100 mL), and argon gas was bubbled through the solution for 5 minutes. Pd2(dba)3 (0.18 g) and SPhos (0.32 g) were then added, and the mixture was heated under reflux for 24 hours with stirring under an argon atmosphere. The reaction solution was subjected to solvent distillation, and the resulting solid was purified by silica gel column chromatography (developing solvent: hexane / toluene) to give compound Inv-13 as a white solid (5.8 g, 90% yield).

[1225] The mass spectrometry analysis showed that the m / e ratio was 675 relative to the molecular weight of 675.84, thus identifying it as compound Inv-13.

[1226] Synthesis Example 14: Synthesis of compound Inv-14

[1227] [Chemical Formula 142]

[1228]

[1229] Using intermediate G (3.5 g) and N-phenylcarbazole-4-boronic acid (3.2 g), under the same conditions as described in (13-2) of Synthesis Example 13, compound Inv-14 was obtained as a white solid (3.1 g, yield 62%).

[1230] The mass spectrometry analysis showed that the m / e ratio was 675 relative to the molecular weight of 675.84, thus identifying it as compound Inv-14.

[1231] Synthesis Example 15: Synthesis of compound Inv-15

[1232] (15-1) Synthesis of intermediate H

[1233] [Chemical Formula 143]

[1234]

[1235] Using intermediate A (5.0 g) and 3,4-difluorophenylboronic acid (2.5 g), under the same conditions as described in Synthesis Example 1, intermediate H was obtained as a white solid (4.3 g, yield 80%).

[1236] (15-2) Synthesis of compound Inv-15

[1237] [Chemical Formula 144]

[1238]

[1239] Using intermediate H (4.3 g), under the same conditions as described in Synthesis Example 3, Inv-15 was obtained as a white solid (5.5 g, yield 79%).

[1240] The mass spectrometry analysis showed that the molecular weight was 764.93 and the m / e ratio was 764, thus identifying it as compound Inv-15.

[1241] Synthesis Example 16: Synthesis of Compound Inv-16

[1242] (16-1) Synthesis of intermediate I

[1243] [Chemical Formula 145]

[1244]

[1245] Using intermediate A (5.0 g) and 3-fluorophenylboronic acid (2.2 g), under the same conditions as described in Synthesis Example 1, intermediate I was obtained as a white solid (4.8 g, yield 92%).

[1246] (16-2) Synthesis of compound Inv-16

[1247] [Chemical Formula 146]

[1248]

[1249] Using intermediate I (4.8 g) and 3,6-diphenylcarbazole (5.0 g), under the same conditions as described in Synthesis Example 3, compound Inv-16 was obtained as a white solid (7.2 g, 90% yield).

[1250] The mass spectrometry analysis showed that the molecular weight was 751.93 and the m / e ratio was 751, thus identifying it as compound Inv-16.

[1251] Synthesis Example 17: Synthesis of compound Inv-17

[1252] [Chemical Formula 147]

[1253]

[1254] Using intermediate B (4.0 g) and [4′-(carbazole-9-yl)-4-biphenyl]boronic acid (3.4 g), under the same conditions as described in Synthesis Example 1, compound Inv-17 was obtained as a white solid (5.0 g, yield 76%).

[1255] The mass spectrometry analysis showed that the molecular weight was 751.93 and the m / e ratio was 751, thus identifying it as compound Inv-17.

[1256] Synthesis Example 18: Synthesis of compound Inv-18

[1257] [Chemical Formula 148]

[1258]

[1259] Using intermediate B (4.5 g) and N-phenylcarbazole-4-boronic acid (3.0 g), under the same conditions as described in Synthesis Example 1, Inv-18 was obtained as a white solid (5.5 g, yield 92%).

[1260] The mass spectrometry analysis showed that the m / e ratio was 675 relative to the molecular weight of 675.84, thus identifying it as compound Inv-18.

[1261] Synthesis Example 19: Synthesis of compound Inv-19

[1262] [Chemical Formula 149]

[1263]

[1264] Using intermediate B (5.0 g) and 3-(N-carbazolyl)phenylboronic acid (3.4 g), under the same conditions as described in Synthesis Example 1, compound Inv-19 was obtained as a white solid (5.6 g, yield 85%).

[1265] The mass spectrometry analysis showed that the m / e ratio was 675 relative to the molecular weight of 675.84, thus identifying it as compound Inv-19.

[1266] Synthesis Example 20: Synthesis of compound Inv-20

[1267] (20-1) Synthesis of intermediate J

[1268] [Chemical Formula 150]

[1269]

[1270] Using intermediate B (5.0 g) and 4-fluorophenylboronic acid (1.6 g), under the same conditions as described in Synthesis Example 1, intermediate J was obtained as a white solid (4.5 g, yield 87%).

[1271] (20-2) Synthesis of compound Inv-20

[1272] [Chemical Formula 151]

[1273]

[1274] Using intermediate J (4.5 g) and carbazole-d8 (2.2 g), under the same conditions as described in Synthesis Example 3, compound Inv-20 was obtained as a white solid (3.8 g, yield 65%).

[1275] The mass spectrometry analysis showed that the m / e ratio was 683 relative to the molecular weight of 683.88, thus identifying it as compound Inv-20.

[1276] Synthesis Example 21: Synthesis of compound Inv-21

[1277] (21-1) Synthesis of intermediate K

[1278] [Chemical Formula 152]

[1279]

[1280] Instead of acetophenone, acetophenone (phenyl-d5) (4.8 g) was used, and intermediate K was obtained as a white solid (5.1 g, yield 30%) according to the synthesis method of intermediate A.

[1281] (21-2) Synthesis of compound Inv-21

[1282] [Chemical Formula 153]

[1283]

[1284] Using intermediate K (3.0 g) and [4′-(carbazole-9-yl)-4-biphenyl]boronic acid (2.5 g), under the same conditions as described in Synthesis Example 1, compound Inv-21 was obtained as a white solid (2.0 g, yield 43%).

[1285] The mass spectrometry analysis showed that, relative to the molecular weight of 680.87, the m / e ratio was 680, thus identifying it as compound Inv-21.

[1286] Alternatively, the compounds of the present invention can also be synthesized via the following synthetic intermediates, according to the conditions described in the synthetic examples.

[1287] [Chemical Formula 154]

[1288]

[1289] [Chemical Formula 155]

[1290]

[1291] [Chemical Formula 156]

[1292]

[1293] [Chemical Formula 157]

[1294]

[1295] [Chemical Formula 158]

[1296]

[1297] [Chemical Formula 159]

[1298]

[1299] [Chemical Formula 160]

[1300]

[1301] Symbol Explanation

[1302] 1.11 Organic EL elements

[1303] 2 substrate

[1304] 3 Anode

[1305] 4 Cathode

[1306] 5. Light-emitting layer

[1307] 6. Hole transport region

[1308] 6a Hole injection layer

[1309] 6b Hole Transport Layer 1

[1310] 6c Hole transport layer 2

[1311] 7a First electron transport layer

[1312] 7b Second electron transport layer

[1313] 10, 20 light-emitting units

Claims

1. An organic electroluminescent element, comprising a cathode, an anode, and an organic layer located between the cathode and the anode. The organic layer comprises a light-emitting layer and an electron transport layer. The electron transport layer comprises compound A, and the luminescent layer comprises host material B. The compound A is represented by formula (1), and the host material B is represented by formula (10-3) or formula (10-4). In the formula, Y 1 For nitrogen atoms, Y 2 For CR; R is a hydrogen atom; Ar 1 and Ar 2 Each is independently a substituted or unsubstituted aryl group with 6 to 18 carbon atoms in a cyclic structure; L 1 and L 2 Each is an arylene group that is either a single bond or substituted or unsubstituted, and has 6 to 18 carbon atoms in a cyclic structure. R 1 ~R 6 It is a hydrogen atom; Selected from R 1 ~R 6 Two adjacent elements in the loop are not bonded to each other and therefore do not form a loop; Cz is represented by either equation (1-a) or equation (1-b); In the formula, Selected from R 21 ~R 28 One of them is connected to L via *a 3 Bonded single bonds; Not through *a and L 3 bonded single bond R 21 ~R 28 Or R 31 ~R 38 All are hydrogen atoms; R a Selected from substituted or unsubstituted aryl groups having 6 to 18 carbon atoms and substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms; *b indicates that L 3 The location of the bond, n is an integer from 1 to 3. When n is 2 or 3, the 2 or 3 Cz are the same or different from each other. L 3 and L 4 Each is an independent single-bonded or substituted or unsubstituted phenylene, wherein, When n is 2 or 3, L 4 For substituted or unsubstituted phenylene, In equation (10-3), R 101A ~R 108A Each is an independent hydrogen atom or a substituted or unsubstituted aryl group with 6 to 18 carbon atoms in a cyclic structure. L 101A It is a single bond or a substituted or unsubstituted cyclic aryl group with 6 to 18 carbon atoms, and 2 L atoms. 101A Choose either the same or different. Ar 101A For substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, 2 Ar atoms 101A Choose either the same or different. In equation (10-4), L 101 Each is independently a single bond, a substituted or unsubstituted aryl group with 6 to 18 carbon atoms in the cyclic ring, or a substituted or unsubstituted divalent heterocyclic group with 5 to 18 cyclic atoms in the cyclic ring; Ar 101 It is an aryl group with 6 to 18 cyclic carbons, either substituted or unsubstituted, or a heterocyclic group with 5 to 18 cyclic atoms, either substituted or unsubstituted. R 101A ~R 108A Each is an independent hydrogen atom or a substituted or unsubstituted aryl group with 6 to 18 carbon atoms in a cyclic structure. X 11 For O, S or N(R) 61 ), R 61 It consists of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 18 carbon atoms. R 62 ~R 69 One of them is connected to L via * 101 Bonded single bonds, Selected from not related to L 101 bonded single bond R 62 ~R 69 At least one set of two adjacent elements may optionally bond to each other to form a substituted or unsubstituted benzene ring or naphthalene ring, or they may not bond to each other and therefore not form a ring. Not with L 101 R bonds that are single bonds and do not form the benzene ring or naphthalene ring 62 ~R 69 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 18 carbon atoms. When expressed as "substituted or unsubstituted", the substituents are each independently selected from unsubstituted phenyl, unsubstituted naphthyl, unsubstituted biphenyl, unsubstituted alkyl with 1 to 6 carbons, and unsubstituted cycloalkyl with 3 to 6 carbons.

2. The organic electroluminescent element according to claim 1, wherein, L 3 and L 4 Each can be a substituted or unsubstituted phenylene.

3. The organic electroluminescent element according to claim 1, wherein, L 3 and L 4 It is a single key.

4. The organic electroluminescent element according to claim 1, wherein, Compound A is represented by formula (1-b-1) or (1-b-2). In the formula, Y 1 Y 2 Ar 1 Ar 2 L 1 L 2 and R 1 ~R 6 Same as the definition in equation (1), R 31 ~R 38 Same as the definition in equation (1-b), R 41 ~R 42 R 44 ~R 45 R 51 ~R 52 and R 54 ~R 55 Each is independently selected from hydrogen atoms, unsubstituted phenyl, unsubstituted naphthyl, unsubstituted biphenyl, and unsubstituted alkyl groups having 1 to 6 carbon atoms.

5. The organic electroluminescent element according to claim 1, wherein, Compound A is represented by any one of the formulas (1-b-11) to (1-b-14). In the formula, Y 1 Y 2 Ar 1 Ar 2 L 1 L 2 and R 1 ~R 6 Same as the definition in equation (1), R 31 ~R 38 Same as the definition in equation (1-b), R 41 R 44 and R 45 Each is independently selected from hydrogen atoms, unsubstituted phenyl groups, unsubstituted naphthyl groups, unsubstituted biphenyl groups, and unsubstituted alkyl groups having 1 to 6 carbon atoms. R 43 It is selected from hydrogen atoms, unsubstituted phenyl groups, unsubstituted naphthyl groups, unsubstituted biphenyl groups, and unsubstituted alkyl groups having 1 to 6 carbon atoms.

6. The organic electroluminescent element according to claim 1, wherein, Compound A is represented by any one of the formulas (1-a-1) to (1-a-4). In the formula, Y 1 Y 2 Ar 1 Ar 2 L 1 L 2 and R 1 ~R 6 Same as the definition in equation (1), R a and R 21 ~R 28 Same as the definition in equation (1-a), R 41 ~R 42 and R 44 ~R 45 Each is independently selected from hydrogen atoms, unsubstituted phenyl, unsubstituted naphthyl, unsubstituted biphenyl, and unsubstituted alkyl groups having 1 to 6 carbon atoms.

7. The organic electroluminescent element according to any one of claims 1 to 6, wherein, L 1 and L 2 One of them is a substituted or unsubstituted aryl group with 6 to 18 carbon atoms in the cyclic ring, and the other one is a single bond.

8. The organic electroluminescent element according to any one of claims 1 to 6, wherein, L 1 and L 2 Each is an arylene group, either substituted or unsubstituted, with 6 to 18 carbon atoms.

9. The organic electroluminescent element according to any one of claims 1 to 6, wherein, L 1 and L 2 The unsubstituted or unsubstituted arylene groups of the cyclic carbon number 6 to 18 are each independently selected from phenylene, biphenylene, naphthylene, and phenanthrene.

10. The organic electroluminescent element according to any one of claims 1 to 6, wherein, Ar 1 and Ar 2 The unsubstituted aryl group representing the substituted or unsubstituted cyclic carbon number of 6 to 18 is independently selected from phenyl, biphenyl, naphthyl, phenanthryl, anthracene, and fluoranthyl.

11. The organic electroluminescent element according to any one of claims 1 to 6, wherein, The molecular weight of compound A is 650 or higher.

12. The organic electroluminescent element according to any one of claims 1 to 6, wherein, The molecular weight of compound A is 650-3000.

13. The organic electroluminescent element according to any one of claims 1 to 6, wherein, The molecular weight of compound A is 650-2000.

14. The organic electroluminescent element according to any one of claims 1 to 6, wherein, Compound A contains at least one deuterium atom.

15. The organic electroluminescent element according to any one of claims 1 to 6, wherein, The main material B is represented by formula (10-6). In the formula, L 101 and Ar 101 Same as the definition in equation (10-4), R 101A ~R 108A Same as the definition in equation (10-4), R 66 ~R 69 Same as the definition in equation (10-4), X 12 It can be O or S.

16. The organic electroluminescent element according to claim 15, wherein, The main material B represented by formula (10-6) is represented by the following formula (10-6H). In the formula, L 101 and Ar 101 Same as the definition in equation (10-4); R 66 ~R 69 Same as the definition in equation (10-4); X 12 It can be O or S.

17. The organic electroluminescent element according to any one of claims 1 to 6, wherein, The main material B is represented by the following formula (10-7), In the formula, L 101 and Ar 101 Same as the definition in equation (10-4), R 101A ~R 108A Same as the definition in equation (10-4), X 11 Same as the definition in equation (10-4), R 62 ~R 69 Same as the definition in equation (10-4), where, selected from R 66 With R 67 R 67 With R 68 and R 68 With R 69 Two adjacent rings in one group bond to each other to form a substituted or unsubstituted benzene ring or naphthalene ring.

18. The organic electroluminescent element according to claim 17, wherein, The main material B represented by formula (10-7) is represented by the following formula (10-7H). In the formula, L 101 and Ar 101 Same as the definition in equation (10-4); X 11 Same as the definition in equation (10-4); R 62 ~R 69 Same as the definition in equation (10-4), where, selected from R 66 With R 67 R 67 With R 68 and R 68 With R 69 Two adjacent rings in one group bond to each other to form a substituted or unsubstituted benzene ring or naphthalene ring.

19. The organic electroluminescent element according to claim 1, wherein, The main material B is represented by formula (10-8). In the formula, L 101 and Ar 101 Same as the definition in equation (10-4), R 101A ~R 108A Same as the definition in equation (10-4), X 12 For O or S, R 66 ~R 69 Same as the definition in equation (10-4), where, selected from R 66 With R 67 R 67 With R 68 and R 68 With R 69 Two adjacent rings in one group bond to each other to form a substituted or unsubstituted benzene ring or naphthalene ring.

20. The organic electroluminescent element according to claim 18 or 19, wherein, Selected from R 66 With R 67 R 67 With R 68 and R 68 With R 69 The two adjacent rings in group 1, as shown in formula (10-8-1), In the formula, The two asterisks are respectively bonded to R. 66 With R 67 R 67 With R 68 and R 68 With R 69 The two adjacent cyclic carbon atoms in group 1 are bonded together. R 80 ~R 83 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 18 carbon atoms.

21. The organic electroluminescent element according to any one of claims 1 to 6, wherein, The main material B is represented by formula (10-9). In the formula, L 101 and Ar 101 Same as the definition in equation (10-4), R 101A ~R 108A Same as the definition in equation (10-4), R 66 ~R 69 Same as the definition in equation (10-4), where, selected from R 66 With R 67 R 67 With R 68 and R 68 With R 69 Two adjacent elements in the loop are not bonded to each other and therefore do not form a loop. X 12 It can be O or S.

22. The organic electroluminescent element according to any one of claims 1 to 6, wherein, The main material B is represented by formula (10-4A). In the formula, L 101 and Ar 101 Same as the definition in equation (10-4), R 101A ~R 108A Each is an independent hydrogen atom or a substituted or unsubstituted aryl group with 6 to 18 carbon atoms in a cyclic structure. X 11 For O, S or N(R) 61 ), R 61 It consists of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 18 carbon atoms. Selected from R 62A ~R 69A The two adjacent rings in group 1, as shown in the formula (10-4A-1), R selected from the ring shown in formula (10-4A-1) 62A ~R 69A One or more adjacent pairs of elements may optionally bond to each other to form a substituted or unsubstituted benzene ring or naphthalene ring, or they may not bond to each other and therefore not form a ring. The ring of formula (10-4A-1) and the R of the substituted or unsubstituted benzene ring or naphthalene ring do not form. 62A ~R 69A Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 18 carbon atoms. In the formula, *1 and *2 are respectively bonded to R 62A ~R 69A The two adjacent cyclic carbon atoms in group 1 are bonded together. R 70 ~R 73 One of them is connected to L via * 101 Bonded single bonds, Not with L 101 bonded single bond R 70 ~R 73 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 18 carbon atoms.

23. The organic electroluminescent element according to any one of claims 1 to 6, wherein, Ar 101 Or Ar 101A The substituted or unsubstituted aryl group with 6 to 18 carbon atoms is phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, benzo[a]phenanthrene, pyrene, phenylenetriethylene, benzo[a]triethylenetriethylene, 9,9-dimethylfluorenyl, benzo-9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl or 9,9'-spirobisfluorenyl.

24. The organic electroluminescent element according to any one of claims 1 to 6, wherein, Ar 101 The substituted or unsubstituted heterocyclic group with 5 to 18 cyclic atoms is dibenzofuranyl, benzodibenzofuranyl, benzofuran-dibenzofuranyl, dibenzothiophenyl, benzodibenzothiophenyl, 9-carbazoyl or 9-phenylcarbazoyl.

25. The organic electroluminescent element according to any one of claims 1 to 6, wherein, L 101 or L 101A The substituted or unsubstituted arylene group with 6 to 18 carbon atoms is phenylene, naphthylene, anthracene, or 9,9-dimethylfluorene-2,7-diyl.

26. The organic electroluminescent element according to any one of claims 1 to 6, wherein, L 101 The unsubstituted or unsubstituted divalent heterocyclic group with 5 to 18 cyclic atoms is a divalent residue of an aromatic heterocycle selected from pyridine, pyrimidine, triazine, carbazole, benzocarbazole, benzofuran, dibenzofuran, naphthobenzofuran, benzothiophene, and dibenzothiophene.

27. The organic electroluminescent element according to any one of claims 1 to 6, wherein, L 101 or L 101A It is a single key.

28. The organic electroluminescent element according to any one of claims 1 to 6, wherein, L 101 or L 101A Each is independently phenylene or naphthylene.

29. The organic electroluminescent element according to any one of claims 1 to 6, wherein, Not with L 101 bonded single bond R 66 ~R 69 Each can be independently a hydrogen atom, a phenyl group, or a naphthyl group.

30. The organic electroluminescent element according to any one of claims 1 to 6, wherein, Not with L 101 bonded single bond R 66 ~R 69 Each can be a hydrogen atom or a phenyl group, independently.

31. The organic electroluminescent element according to any one of claims 1 to 6, wherein, Not with L 101 bonded single bond R 66 ~R 69 All are hydrogen atoms.

32. The organic electroluminescent element according to any one of claims 1 to 6, wherein, R 101A ~R 108A All are hydrogen atoms.

33. The organic electroluminescent element according to any one of claims 1 to 6, wherein, The light-emitting layer contains phosphorescent dopant material.

34. The organic electroluminescent element according to any one of claims 1 to 6, wherein, The light-emitting layer contains fluorescent dopant material.

35. The organic electroluminescent element according to claim 1, wherein, Compound A is selected from the following compounds: 。 36. The organic electroluminescent element according to claim 1, wherein, The host material B is selected from the following compounds: 。 37. An electronic device comprising an organic electroluminescent element according to any one of claims 1 to 36.

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