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

Abstract

A compound represented by the following formula (1), an organic electroluminescent element including the compound, and an electronic device including such an organic electroluminescent element. In formula (1), Ar 1 , Ar 2 , L 1 , and p are as defined in the specification, and A is a group represented by formula (2). In formula (2), HAr 2 , m, n, L 2 , and * are as defined in the specification, and HAr 1 is a group represented by formula (3). In formula (3), Y 1 , X 1 , X 8 , *a, and ** are as defined in the specification.

Description

Technical Field

[0001] This invention relates to compounds, materials for organic electroluminescent elements, organic electroluminescent elements, and electronic devices comprising the 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, developing materials that efficiently transport electrons or holes to the luminescent region and facilitate electron-hole recombination is important for obtaining high-performance organic EL devices.

[0003] Patent documents 1-14 disclose compounds used as materials for organic electroluminescent elements.

[0004] Existing technical documents

[0005] Patent documents

[0006] Patent Document 1: WO2013 / 077352A1 Publication

[0007] Patent Document 2: WO2020 / 130724A1 Publication

[0008] Patent Document 3: WO2020 / 209679A1 Publication

[0009] Patent Document 4: WO2020 / 209678A1

[0010] Patent Document 5: KR2020-0075555A Publication

[0011] Patent Document 6: KR2020-0068397A Publication

[0012] Patent Document 7: KR2018-0040296A Publication

[0013] Patent Document 8: US2017 / 0155048A1

[0014] Patent Document 9: WO2018 / 230969A1

[0015] Patent Document 10: US2020 / 0079735A1 Publication

[0016] Patent Document 11: WO2016 / 089080A1 Publication

[0017] Patent Document 12: WO2016 / 084962A1

[0018] Patent Document 13: WO2019 / 191665A1 Publication

[0019] Patent Document 14: WO2017 / 179809A1 Publication Summary of the Invention

[0020] The problem the invention aims to solve

[0021] In the past, a large number of compounds for organic EL devices have been reported, but we are still looking for compounds that can further improve the performance of organic EL devices.

[0022] The present invention was made to solve the above-mentioned problems, and aims to provide compounds that further improve the performance of organic EL elements, organic EL elements that further improve the performance of elements, and electronic devices comprising such organic EL elements.

[0023] means for solving problems

[0024] The inventors conducted an in-depth study on the performance of organic EL elements containing compounds described in Patent Documents 1 to 14, and found that organic EL elements containing compounds represented by the following formula (1) exhibit higher efficiency.

[0025] In one embodiment, the present invention provides a compound represented by the following formula (1).

[0026] [Chemical Formula 1]

[0027]

[0028] (In formula (1),)

[0029] A is the group shown in formula (2).

[0030] [Chemical Formula 2]

[0031]

[0032] (In formula (2),)

[0033] HAr 1 The group is shown in formula (3).

[0034] m is an integer from 1 to 4.

[0035] n is an integer from 1 to 4.

[0036] m+n is an integer from 2 to 5.

[0037] When m+n is 2, L2 is a trivalent linker.

[0038] When m+n is 3 to 5, L 2 It consists of tetravalent to hexavalent linking groups, with multiple HAr 1 They can be the same or different; multiple HArs 2 They can be the same or different.

[0039] The above linking groups are

[0040] Substituted or unsubstituted phenylene.

[0041] * indicates the bonding position with the central pyrimidine ring.

[0042] [Chemical Formula 3]

[0043]

[0044] (In formula (3),)

[0045] Y 1 It consists of oxygen or sulfur atoms.

[0046] X 1 ~X 8 Each is independently a nitrogen atom or CR 1 ,

[0047] R 1 for

[0048] hydrogen atom,

[0049] Halogen atoms,

[0050] Nitro,

[0051] cyano,

[0052] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0053] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0054] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0055] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0056] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0057] -O-(R 904 The groups shown in the figure,

[0058] -S-(R 905 The groups shown in the figure,

[0059] -N(R 906 (R) 907 The groups shown in the figure,

[0060] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0061] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0062] R 901 ~R 907 Each independently

[0063] hydrogen atom,

[0064] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0065] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0066] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0067] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0068] In R 901 In the case of two or more R, two or more R 901 They are the same or different.

[0069] In R 902 In the case of two or more R, two or more R 902 They are the same or different.

[0070] In R 903 In the case of two or more R, two or more R 903 They are the same or different.

[0071] In R 904 In the case of two or more R, two or more R 904 They are the same or different.

[0072] In R 905 In the case of two or more R, two or more R 905 They are the same or different.

[0073] In R 906 In the case of two or more R, two or more R 906 They are the same or different.

[0074] In R 907 In the case of two or more R, two or more R 907 They are the same or different.

[0075] Multiple R1 They can bond together to form a ring.

[0076] in,

[0077] Selected from X 1 ~X 8 One of them is a carbon atom bonded to *a.

[0078] ** indicates that it is related to L 1 The bonding position,

[0079] R 1 Excluding dibenzofuranyl,

[0080] In multiple R 1 When the rings are formed by mutual bonding and the rings are carbon-fused rings, the number of carbon atoms in the carbon-fused rings is 17 or less.

[0081] HAr 2 It is an aryl group with 6 to 12 carbon atoms, either substituted or unsubstituted.

[0082] Among them, the above-mentioned HAr 2 The substituents used in the above description of "substituted or unsubstituted" do not include nitrogen-containing groups.

[0083] Ar 1 for

[0084] hydrogen atom,

[0085] Halogen atoms,

[0086] Nitro,

[0087] cyano,

[0088] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0089] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0090] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0091] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0092] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0093] -O-(R 904 The groups shown in the figure,

[0094] -S-(R 905 The groups shown in the figure,

[0095] -N(R906 (R) 907 The groups shown in the figure,

[0096] Substituted or unsubstituted aryl groups with 6 to 12 carbon atoms

[0097] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or

[0098] The group shown in formula (2) above,

[0099] R 901 ~R 907 Same as above.

[0100] Ar 2 for

[0101] hydrogen atom,

[0102] Halogen atoms,

[0103] Nitro,

[0104] cyano,

[0105] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0106] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0107] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0108] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0109] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0110] -O-(R 904 The groups shown in the figure,

[0111] -S-(R 905 The groups shown in the figure,

[0112] -N(R 906 (R) 907 The groups shown in the figure,

[0113] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms

[0114] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or

[0115] The group shown in formula (2) above,

[0116] R 901 ~R 907Same as above.

[0117] L 1 It is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms in a cyclic structure.

[0118] p is 0 or 1, (L) 1 0 refers to a single bond.

[0119] In another embodiment, the present invention provides a material for an organic EL element comprising the compound shown in formula (1) above.

[0120] In another embodiment, the present invention provides an organic electroluminescent element having a cathode, an anode, and an organic layer located between the cathode and the anode, the organic layer comprising a light-emitting layer, at least one layer of the organic layer comprising a compound represented by formula (1) above.

[0121] In another embodiment, the present invention provides an electronic device comprising the aforementioned organic electroluminescent element.

[0122] The effects of the invention

[0123] Organic EL elements containing the compound shown in formula (1) above exhibit improved element performance. Attached Figure Description

[0124] [ Figure 1 [Illustration] is a schematic diagram illustrating an example of the layer structure of an organic EL element according to one aspect of the present invention.

[0125] [ Figure 2 [Illustration] 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

[0126] [definition]

[0127] In this specification, a hydrogen atom means an isotope containing different numbers of neutrons, namely protium, deuterium, and tritium.

[0128] 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.

[0129] 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.

[0130] 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.

[0131] 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.

[0132] 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 in substituents is not included. Here, "YY" is greater than "XX," where "XX" refers to an integer greater than 1, and "YY" refers to an integer greater than 2.

[0133] 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.

[0134] In this specification, "unsubstituted ZZ group" means "substituted or unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".

[0135] 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.

[0136] 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.

[0137] Substituents described in this specification

[0138] The substituents described in this specification are explained below. Unless otherwise specified, the substituents described in this specification are defined as follows.

[0139] 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.

[0140] 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.

[0141] 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.

[0142] 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.

[0143] 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.

[0144] 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.

[0145] 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.

[0146] 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.

[0147] 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.

[0148] • "Substituted or unsubstituted aryl groups"

[0149] 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.

[0150] "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.

[0151] • Unsubstituted aryl groups (specific example group G1A):

[0152] phenyl,

[0153] p-phenyl,

[0154] metaphenyl,

[0155] o-phenyl,

[0156] p-terphenyl-4-yl,

[0157] p-terphenyl-3-yl,

[0158] p-terphenyl-2-yl,

[0159] m-terphenyl-4-yl,

[0160] m-terphenyl-3-yl,

[0161] m-terphenyl-2-yl,

[0162] m-terphenyl-3'-yl,

[0163] o-terphenyl-4-yl

[0164] o-terphenyl-3-yl

[0165] o-terphenyl-2-yl,

[0166] 1-Naphthyl,

[0167] 2-Naphthyl,

[0168] anthracene,

[0169] Benzanthracene,

[0170] Fiki,

[0171] Benzphenanthrene, phenatenyl,

[0172] Pyrene

[0173] base,

[0174] benzo[a] base,

[0175] Tri-phenylene,

[0176] Benzotrimethylene

[0177] phenylene,

[0178] Pentaphenyl,

[0179] Fluorine

[0180] 9,9'-spirobisfluorene,

[0181] benzo[f]fluorene,

[0182] Dibenzofluorene,

[0183] Fluoranthene base,

[0184] Benzofluoranthyl,

[0185] Peripheral, and

[0186] 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).

[0187] [Chemical Formula 4]

[0188]

[0189] [Chemical Formula 5]

[0190]

[0191] • Substituted aryl groups (specific example group G1B):

[0192] o-Tolyl,

[0193] m-Tolyl,

[0194] p-Tolyl,

[0195] p-Xylyl,

[0196] m-Xylyl,

[0197] o-xylyl,

[0198] p-isopropylphenyl,

[0199] m-Isopropylphenyl,

[0200] o-isopropylphenyl,

[0201] p-tert-butylphenyl,

[0202] m-tert-butylphenyl,

[0203] o-tert-butylphenyl,

[0204] 3,4,5-Trimethylphenyl,

[0205] 9,9-Dimethylfluorenyl,

[0206] 9,9-Diphenylfluorenyl

[0207] 9,9-bis(4-methylphenyl)fluorenyl,

[0208] 9,9-Bis(4-isopropylphenyl)fluorenyl,

[0209] 9,9-Bis(4-tert-butylphenyl)fluorenyl,

[0210] cyanophenyl,

[0211] Triphenylsilylphenyl

[0212] Trimethylsilylphenyl

[0213] Phenynaphthyl,

[0214] Naphthylphenyl and

[0215] 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.

[0216] • "Substituted or unsubstituted heterocyclic groups"

[0217] 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.

[0218] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.

[0219] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0220] 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".

[0221] "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.

[0222] 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).

[0223] 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).

[0224] • Unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1):

[0225] pyrrole,

[0226] Imidazole group,

[0227] Pyrazolyl,

[0228] Triazole group,

[0229] Tetraazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyridinyl, pyridinyl, pyrazinyl, triazinyl, indoleyl, isindoleyl, indazinyl, quinazinyl, quinolinyl, isoquinolinyl, cinolinyl, phthalazinyl, quinazolinyl, quinoxolinyl, benzimidazolyl, indoleyl, phenanthrolinel, phenanthridyl, acridineyl, phenazinyl, carbazoleyl, benzocarbazoleyl

[0230] Morpholinyl

[0231] phenoxazine group,

[0232] phenothiazine group,

[0233] Azacarbazolyl and diazacarbazolyl.

[0234] • Unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2):

[0235] furanyl,

[0236] Oxazolyl,

[0237] Isoxazolyl,

[0238] Oxadiazole group,

[0239] Xuton base,

[0240] Benzofuranyl,

[0241] Isobenzofuranyl,

[0242] Dibenzofuranyl,

[0243] Naphthobenzofuranyl,

[0244] Benzoxazolyl,

[0245] Benzisoxazole group,

[0246] phenoxazine group,

[0247] Morpholinyl

[0248] Dinaphthylfuranyl,

[0249] Azadibenzofuranyl,

[0250] diazadibenzofuranyl,

[0251] Azanaphthalenebenzofuranyl and

[0252] Diazanaphthenebenzofuranyl.

[0253] • Unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3):

[0254] Thiophene group

[0255] Thiazole group,

[0256] Isothiazolyl,

[0257] Thiadiazole group,

[0258] benzothienyl

[0259] isobenzothienyl

[0260] dibenzothienyl

[0261] Naphthobenzothienyl

[0262] Benzothiazolyl,

[0263] Benzisothiazolyl,

[0264] phenothiazine group,

[0265] dinaphthothienyl

[0266] azadibenzothienyl

[0267] diazadibenzothienyl

[0268] Azanaphthobenzothienyl, and

[0269] diazanaphthobenzothienyl.

[0270] • 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):

[0271] [Chemical Formula 6]

[0272]

[0273] [Chemical Formula 7]

[0274]

[0275] 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.

[0276] 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.

[0277] • Heterocyclic groups containing nitrogen atoms (specific example group G2B1):

[0278] (9-phenyl)carbazole group,

[0279] (9-Biphenyl)carbazolyl,

[0280] (9-Phenyl)phenylcarbazolyl,

[0281] (9-Naphthyl)carbazole,

[0282] Diphenylcarbazole-9-yl,

[0283] Phenylexacarbazole-9-yl,

[0284] Methylbenzimidazole,

[0285] Ethylbenzimidazole,

[0286] Phenylacetyl,

[0287] Biphenyltriazine

[0288] diphenyltriazine group,

[0289] phenylquinazolinyl and

[0290] Biphenylquinazolinyl.

[0291] • Heterocyclic groups containing oxygen atoms (specific example group G2B2):

[0292] Phenyl dibenzofuranyl,

[0293] Methyldibenzofuranyl,

[0294] tert-butyldibenzofuranyl and

[0295] The monovalent residue of [9H-xanton-9,9'-[9H]fluorene].

[0296] • Heterocyclic groups containing sulfur atoms (specific example group G2B3):

[0297] Phenyl dibenzothiophene,

[0298] Methyldibenzothiophene,

[0299] tert-butyldibenzothiophene and

[0300] The monovalent residue of [9H-thiophene-9,9'-[9H]fluorene].

[0301] • 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):

[0302] The aforementioned "one or more hydrogen atoms in a monovalent heterocyclic group" refers to hydrogen atoms bonded to the cyclic carbon atoms of the monovalent heterocyclic group, X A and Y A The hydrogen atom bonded to the nitrogen atom when at least one of them is NH and X A and Y A One of them is one or more hydrogen atoms in the methylene group when CH2 is present.

[0303] • "Substituted or unsubstituted alkyl groups"

[0304] 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.

[0305] "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.

[0306] • Unsubstituted alkyl groups (specific example group G3A):

[0307] methyl,

[0308] Ethyl,

[0309] n-propyl,

[0310] Isopropyl,

[0311] n-Butyl,

[0312] Isobutyl,

[0313] sec-butyl, and

[0314] tert-butyl.

[0315] • Substituted alkyl groups (specific example group G3B):

[0316] Heptafluoropropyl (including isomers),

[0317] Pentafluoroethyl,

[0318] 2,2,2-Trifluoroethyl and

[0319] Trifluoromethyl

[0320] • "Substituted or unsubstituted alkenyl groups"

[0321] 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.

[0322] "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.

[0323] • Unsubstituted alkenyl groups (specific example group G4A):

[0324] vinyl,

[0325] Allyl

[0326] 1-Butenyl,

[0327] 2-Butenyl, and

[0328] 3-Butenyl.

[0329] • Substituted alkenyl groups (specific example group G4B):

[0330] 1,3-Butadienyl,

[0331] 1-Methylvinyl

[0332] 1-Methylallyl,

[0333] 1,1-Dimethylallyl,

[0334] 2-Methylallyl, and

[0335] 1,2-Dimethylallyl.

[0336] • "Substituted or unsubstituted alkynyl groups"

[0337] 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".

[0338] "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.

[0339] • Unsubstituted alkynyl group (specific example group G5A):

[0340] Acetylene group.

[0341] • "Substituted or unsubstituted cycloalkyl groups"

[0342] 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.

[0343] "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.

[0344] • Unsubstituted cycloalkyl groups (specific example group G6A):

[0345] Cyclopropyl,

[0346] Cyclobutyl,

[0347] Cyclopentyl,

[0348] Cyclohexyl,

[0349] 1-Adamantyl,

[0350] 2-Adamantyl,

[0351] 1-norborneol, and

[0352] 2-norborneol.

[0353] • Substituted cycloalkyl groups (specific example group G6B):

[0354] 4-Methylcyclohexyl.

[0355] ·"-Si(R 901 (R) 902 (R) 903 The group shown in the figure”

[0356] 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:

[0357] -Si(G1)(G1)(G1),

[0358] -Si(G1)(G2)(G2),

[0359] -Si(G1)(G1)(G2),

[0360] -Si(G2)(G2)(G2),

[0361] -Si(G3)(G3)(G3), and

[0362] -Si(G6)(G6)(G6)

[0363] Here,

[0364] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0365] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0366] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0367] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0368] In -Si(G1)(G1)(G1), multiple G1s may be the same or different from each other.

[0369] In -Si(G1)(G2)(G2), multiple G2s may be the same or different from each other.

[0370] In -Si(G1)(G1)(G2), multiple G1s may be the same or different from each other.

[0371] In -Si(G2)(G2)(G2), multiple G2s may be the same or different from each other.

[0372] In -Si(G3)(G3)(G3), multiple G3s may be the same or different from each other.

[0373] In -Si(G6)(G6)(G6), multiple G6s may be the same or different from each other.

[0374] ·“-O-(R 904 The group shown in the figure”

[0375] As described in this specification, -O-(R) 904 Specific examples of the group shown in the figure (specific example group G8) can be given as follows:

[0376] -O(G1)

[0377] -O(G2),

[0378] -O(G3) and

[0379] -O(G6).

[0380] Here,

[0381] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0382] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0383] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0384] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0385] ·“-S-(R 905 The group shown in the figure”

[0386] As described in this specification, -S-(R) 905 Specific examples of the group shown in the figure (specific example group G9) can be given as follows:

[0387] -S(G1)

[0388] -S(G2),

[0389] -S(G3) and

[0390] -S(G6).

[0391] Here,

[0392] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0393] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0394] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0395] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0396] ·"-N(R 906 (R) 907 The group shown in the figure”

[0397] 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:

[0398] -N(G1)(G1),

[0399] -N(G2)(G2),

[0400] -N(G1)(G2),

[0401] -N(G3)(G3) and

[0402] -N(G6)(G6).

[0403] Here,

[0404] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0405] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0406] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0407] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0408] In -N(G1)(G1), multiple G1s may be the same or different from each other.

[0409] In -N(G2)(G2), multiple G2 values ​​may be the same or different from each other.

[0410] In -N(G3)(G3), multiple G3s may be the same or different from each other.

[0411] In -N(G6)(G6), multiple G6 values ​​may be the same or different from each other.

[0412] • "Halogen atom"

[0413] Specific examples of "halogen atoms" described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0414] • "Substituted or unsubstituted fluoroalkyl groups"

[0415] 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.

[0416] • "Substituted or unsubstituted haloalkyl groups"

[0417] 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.

[0418] • "Substituted or unsubstituted alkoxy groups"

[0419] 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.

[0420] • "Substituted or unsubstituted alkylthio groups"

[0421] 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.

[0422] • "Substituted or unsubstituted aryloxy groups"

[0423] 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.

[0424] • "Substituted or unsubstituted arylthio groups"

[0425] 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.

[0426] • "Substituted or unsubstituted trialkylsilyl groups"

[0427] 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.

[0428] • "Substituted or unsubstituted aralkyl groups"

[0429] 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.

[0430] 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.

[0431] 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.

[0432] 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.

[0433] In this specification, the carbazoyl group, unless otherwise specified herein, specifically refers to any one of the following groups.

[0434] [Chemical Formula 8]

[0435]

[0436] In this specification, (9-phenyl)carbazolyl refers specifically to any one of the following groups unless otherwise specified herein.

[0437] [Chemical Formula 9]

[0438]

[0439] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.

[0440] In this specification, dibenzofuranyl and dibenzothiopheneyl are specifically any one of the following groups unless otherwise stated in this specification.

[0441] [Chemical Formula 10]

[0442]

[0443] In the above general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.

[0444] 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.

[0445] • "Substituted or unsubstituted aryl groups"

[0446] Unless otherwise stated, the "substituted or unsubstituted aryl group" described in this specification refers to a divalent group derived from the "substituted or unsubstituted aryl group" by removing one hydrogen atom from the aryl 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 aryl ring.

[0447] • "Substituted or unsubstituted divalent heterocyclic groups"

[0448] 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.

[0449] • "Substituted or unsubstituted alkylene compounds"

[0450] 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.

[0451] 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).

[0452] [Chemical Formula 11]

[0453]

[0454] [Chemical Formula 12]

[0455]

[0456] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0457] In the above general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.

[0458] [Chemical Formula 13]

[0459]

[0460] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0461] Formulas Q9 and Q 10 They can form rings by bonding with each other via single bonds.

[0462] In the above general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.

[0463] [Chemical Formula 14]

[0464]

[0465] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0466] In the above general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.

[0467] 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).

[0468] [Chemical Formula 15]

[0469]

[0470] [Chemical Formula 16]

[0471]

[0472] [Chemical Formula 17]

[0473]

[0474] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0475] [Chemical Formula 18]

[0476]

[0477] [Chemical Formula 19]

[0478]

[0479] [Chemical Formula 20]

[0480]

[0481] [Chemical Formula 21]

[0482]

[0483] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0484] The above is an explanation of "substituents described in this specification".

[0485] • "Cases where bonds form rings"

[0486] 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".

[0487] The following description addresses the cases described in this specification as "forming a substituted or unsubstituted monocyclic ring by bonding one or more groups of two or more adjacent elements together" and "forming a substituted or unsubstituted fused ring by bonding one or more groups of two or more adjacent elements together" (hereinafter, these cases are sometimes collectively referred to as "forming a ring by bonding"). The case of anthracene compounds represented by the following general formula (TEMP-103) with an anthracene ring as the parent skeleton will be used as an example.

[0488] [Chemical Formula 22]

[0489]

[0490] For example, in the case of 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.

[0491] The phrase "one or more groups" refers to the fact that two or more groups consisting of two or more adjacent elements 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).

[0492] [Chemical Formula 23]

[0493]

[0494] The formation of rings from "groups consisting of two or more adjacent elements" includes not only the case of bonds formed by groups consisting of "two" adjacent elements, as in the previous example, but also the case of bonds formed by groups consisting of "three or more" adjacent elements. For example, this 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 .

[0495] [Chemical Formula 24]

[0496]

[0497] 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 a "single ring" or "fused ring" is formed from "one of two adjacent groups," the "single ring" or "fused ring" can still form 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.

[0498] "Unsaturated rings" refer to aromatic hydrocarbon rings or aromatic heterocycles. "Saturated rings" refer to aliphatic hydrocarbon rings or non-aromatic heterocycles.

[0499] 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.

[0500] 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.

[0501] 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.

[0502] "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.

[0503] 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.

[0504] 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.

[0505] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".

[0506] Unless otherwise stated in this specification, "unsaturated ring" is preferred over "saturated ring".

[0507] Unless otherwise stated in this specification, "monocyclic" is preferably a benzene ring.

[0508] Unless otherwise stated in this specification, the "unsaturated ring" is preferably a benzene ring.

[0509] In the case of "one or more groups consisting of two or more adjacent atoms" or "forming a substituted or unsubstituted monocyclic ring by mutual bonding" or "forming a substituted or unsubstituted fused ring by mutual bonding", unless otherwise stated in this specification, it is preferred that one or more groups consisting of two or more adjacent atoms form an "unsaturated ring" formed by mutual bonding of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur.

[0510] 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.

[0511] 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.

[0512] The above explains the cases of "a single ring formed by bonding one or more groups of two or more adjacent elements together, whether substituted or unsubstituted" and "a fused ring formed by bonding one or more groups of two or more adjacent elements together, whether substituted or unsubstituted" ("the case of forming a ring by bonding").

[0513] Substituents when described as "substituted or unsubstituted"

[0514] 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.

[0515] Unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0516] Unsubstituted acetylinyl groups with 2 to 50 carbon atoms

[0517] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0518] -Si(R 901 (R) 902 (R) 903 ),

[0519] -O-(R 904 ),

[0520] -S-(R 905 ),

[0521] -N(R 906 (R) 907 ),

[0522] Halogen atom, cyano group, nitro group,

[0523] Unsubstituted aryl groups with 6 to 50 carbon atoms and

[0524] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms

[0525] Groups, etc., in the composition group

[0526] Here, R 901 ~R 907 Each independently

[0527] hydrogen atom,

[0528] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0529] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0530] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0531] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0532] 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.

[0533] 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.

[0534] 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.

[0535] 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.

[0536] 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.

[0537] 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.

[0538] 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.

[0539] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.

[0540] Alkyl groups with 1 to 50 carbon atoms

[0541] Aryl groups with 6 to 50 carbon atoms and

[0542] Heterocyclic groups with 5 to 50 cyclic atoms

[0543] The groups in the group.

[0544] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.

[0545] Alkyl groups having 1 to 18 carbon atoms

[0546] aryl groups with 6 to 18 carbon atoms and

[0547] Heterocyclic groups with 5 to 18 cyclic atoms

[0548] The groups in the group.

[0549] Specific examples of the substituents mentioned above are those described in the section "Substituents as set forth in this specification".

[0550] 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.

[0551] 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.

[0552] In this specification, the numerical range represented by "AA~BB" refers to the range included by taking the value AA, which is written before "AA~BB", as the lower limit and the value BB, which is written after "AA~BB", as the upper limit.

[0553] The compounds of the present invention will be described below.

[0554] The compounds of the present invention are represented by the following formula (1). Hereinafter, the compounds of the present invention represented by formula (1) and the formulas contained in formula (1) described below are sometimes referred to simply as "inventive compounds".

[0555] [Chemical Formula 25]

[0556]

[0557] The symbols in equation (1) and the expressions contained in equation (1) will be explained below. It should be noted that the same symbols have the same meaning.

[0558] In equation (1),

[0559] A is the group shown in formula (2).

[0560] [Chemical Formula 26]

[0561]

[0562] In equation (2),

[0563] HAr 1 The group is shown in formula (3).

[0564] m is an integer from 1 to 4, preferably 1.

[0565] n is an integer from 1 to 4, preferably 1.

[0566] m+n is an integer from 2 to 5, preferably 2.

[0567] When m+n is 2, L 2 It is a trivalent linker.

[0568] When m+n is 3 to 5, L 2 It consists of tetravalent to hexavalent linking groups, with multiple HAr 1 They can be the same or different; multiple HArs 2 They can be the same or different.

[0569] The linking group mentioned above is a substituted or unsubstituted phenylene group.

[0570] * indicates the bonding position with the central pyrimidine ring.

[0571] [Chemical Formula 27]

[0572]

[0573] In equation (3),

[0574] Y 1 It consists of oxygen or sulfur atoms.

[0575] As a solution, Y 1 Oxygen atoms are preferred. Alternatively, sulfur atoms are preferred.

[0576] X 1 ~X 8 Each is independently a nitrogen atom or CR 1 ,

[0577] R 1 for

[0578] hydrogen atom,

[0579] Halogen atoms,

[0580] Nitro,

[0581] cyano,

[0582] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0583] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0584] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0585] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0586] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0587] -O-(R 904 The groups shown in the figure,

[0588] -S-(R 905 The groups shown in the figure,

[0589] -N(R 906 (R) 907 The groups shown in the figure,

[0590] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0591] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0592] R 901 ~R 907 Each independently

[0593] hydrogen atom,

[0594] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0595] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0596] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0597] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0598] In R 901 In the case of two or more R, two or more R 901 They are the same or different.

[0599] In R 902 In the case of two or more R, two or more R 902 They are the same or different.

[0600] In R 903 In the case of two or more R, two or more R 903 They are the same or different.

[0601] In R 904 In the case of two or more R, two or more R 904 They are the same or different.

[0602] In R 905 In the case of two or more R, two or more R 905 They are the same or different.

[0603] In R 906 In the case of two or more R, two or more R 906 They are the same or different.

[0604] In R 907 In the case of two or more R, two or more R 907 They are the same or different.

[0605] Multiple R 1 They can bond with each other to form substituted or unsubstituted rings.

[0606] in,

[0607] Selected from X 1 ~X 8 One of them is a carbon atom bonded to *a.

[0608] ** indicates that it is related to L 1 The bonding position,

[0609] R 1 Excluding dibenzofuranyl,

[0610] In multiple R 1 When the rings are formed by mutual bonding and the rings are carbon-fused rings, the number of carbon atoms in the carbon-fused rings is 17 or less.

[0611] X 1 ~X 8 CR is preferred 1 .

[0612] R 1 Preferably, it is 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; more preferably, 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; and even more preferably, it is a hydrogen atom.

[0613] The details of the halogen atom are the same as those described in the "Substituents Described in this Specification" section above, and fluorine atoms are preferred.

[0614] The details of the substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms are the same as those described in the "Substituents Described in this Specification" section above.

[0615] The unsubstituted alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, or n-pentyl, more preferably methyl, ethyl, isopropyl, or tert-butyl, and even more preferably methyl or tert-butyl.

[0616] The details of the substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms are the same as those described in the "Substituents Described in this Specification" section above.

[0617] The unsubstituted alkenyl group is preferably vinyl or allyl.

[0618] The details of the substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms are the same as those described in the "Substituents Described in this Specification" section above.

[0619] The details of the substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms are the same as those described in the "Substituents Described in this Specification" section above.

[0620] The unsubstituted cycloalkyl group is preferably cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl, more preferably cyclopropyl, cyclopentyl, or cyclohexyl.

[0621] The above-mentioned -Si(R) 901 (R) 902 (R) 903 ), the above-mentioned -O-(R 904 The group shown is -S-(R) 905 The groups shown are -N(R) 906 (R) 907The details of the groups shown are the same as those described in "Substituents as described in this specification" above.

[0622] The details of the substituted or unsubstituted aryl groups with 6 to 50 carbon atoms are the same as those described in the "Substituents Described in this Specification" section above.

[0623] The unsubstituted aryl group is preferably phenyl, biphenyl, naphthyl, or terphenyl, more preferably phenyl, biphenyl, or naphthyl, further preferably phenyl, p-biphenyl, meta-biphenyl, o-biphenyl, 1-naphthyl, or 2-naphthyl, and even more preferably phenyl.

[0624] The details of the aforementioned substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms are the same as those described in the "Substituents Described in this Specification" section above. Dibenzofuran group is excluded.

[0625] The unsubstituted heterocyclic group is preferably pyrrole, imidazolyl, pyrazolyl, triazolyl, thiophene, oxazolyl, thiazolyl, pyridinyl, pyridazinyl, pyrazinyl, or triazinyl.

[0626] R 901 ~R 907 Details of each group indicated and for R 1 The details of the corresponding functional groups described are the same, and the preferred functional groups are also the same. Among them, dibenzofuran group is specified.

[0627] The above multiple R 1 The details of the optional substituted or unsubstituted rings formed by mutual bonding are the same as those described in “Substituents described in this specification” above, and are selected from substituted or unsubstituted aromatic hydrocarbon rings, substituted or unsubstituted aliphatic hydrocarbon rings, substituted or unsubstituted aromatic heterocycles, and substituted or unsubstituted non-aromatic heterocycles.

[0628] It should be noted that, in the case where the substituted or unsubstituted ring is a carbon-fused ring, the "number of carbon atoms in the ring" is defined to include X. 1 ~X 4 or X 5 ~X 8 CR 1 The amount of C (carbon). For example, in the case where equation (3) is represented by the following equation (3-1) (X 1 ~X 4 For CR 1 X 1 and X 2 Each of their own R 1 (forming a ring by mutual bonding), R 1 The number of carbon atoms in the ring (carbon fused ring) formed by mutual bonding is 10.

[0629] [Chemical Formula 28]

[0630]

[0631] In equation (3-1), Y 1 X 5 ~X 8 The definitions of , *a, and ** are the same as those in equation (3).

[0632] In multiple R 1 When the rings are formed by mutual bonding and the rings are carbon-fused rings, the number of carbon atoms in the carbon-fused rings is preferably 14 or less, more preferably 10 or less.

[0633] The aforementioned aromatic hydrocarbon ring is, for example, a benzene ring, a naphthalene ring, a phenanthrene ring, or a fluorene ring, preferably a naphthalene ring or a fluorene ring.

[0634] The aforementioned aliphatic hydrocarbon rings are, for example, cyclopentene rings, cyclopentadiene rings, cyclohexene rings, cyclohexadiene rings, or hydrocarbon rings obtained by partially hydrogenating the aforementioned aromatic hydrocarbon rings.

[0635] The aforementioned aromatic heterocycles are, 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, preferably dibenzofuran rings, dibenzothiophene rings, or carbazole rings.

[0636] The aforementioned non-aromatic heterocycles are, for example, heterocycles obtained by partially hydrogenating the aforementioned aromatic heterocycles.

[0637] As a solution, X is preferred. 2 or X 7 As another option, X is preferred for the carbon atom bonded to *a. 4 or X 5 For the carbon atom bonded to *a.

[0638] HAr 2 It is an aryl group with 6 to 12 carbon atoms, either substituted or unsubstituted.

[0639] Among them, the above-mentioned HAr 2 The substituents used in the above description of "substituted or unsubstituted" do not include nitrogen-containing groups.

[0640] The unsubstituted aryl group is preferably phenyl, biphenyl, or naphthyl, more preferably phenyl or naphthyl, and even more preferably phenyl.

[0641] Ar 1 for

[0642] hydrogen atom,

[0643] Halogen atoms,

[0644] Nitro,

[0645] cyano,

[0646] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0647] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0648] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0649] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0650] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0651] -O-(R 904 The groups shown in the figure,

[0652] -S-(R 905 The groups shown in the figure,

[0653] -N(R 906 (R) 907 The groups shown in the figure,

[0654] Substituted or unsubstituted aryl groups with 6 to 12 carbon atoms

[0655] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or

[0656] The group shown in formula (2) above,

[0657] R 901 ~R 907 With R 1 The definitions are the same.

[0658] Ar 1 Preferably, it is an aryl group with 6 to 12 carbon atoms, either substituted or unsubstituted.

[0659] Ar 1 Details of the groups other than the substituted or unsubstituted aryl groups with 6 to 12 carbon atoms and the substituted or unsubstituted heterocyclic groups with 5 to 50 carbon atoms, and those related to R. 1 The details of the corresponding functional groups recorded are the same, and the preferred functional groups are also the same.

[0660] As Ar 1The substituted or unsubstituted aryl group with 6 to 12 carbon atoms mentioned above can be phenyl, biphenyl, or naphthyl, for example. The aryl group is preferably phenyl.

[0661] Ar 1 The details of the heterocyclic groups with 5 to 50 cyclic atoms, whether substituted or unsubstituted, are the same as those described in the "Substituents Described in this Specification" section above.

[0662] The unsubstituted heterocyclic group is preferably dibenzofuranyl or dibenzothiophenyl.

[0663] Ar 2 for

[0664] hydrogen atom,

[0665] Halogen atoms,

[0666] Nitro,

[0667] cyano,

[0668] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0669] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0670] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0671] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0672] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0673] -O-(R 904 The groups shown in the figure,

[0674] -S-(R 905 The groups shown in the figure,

[0675] -N(R 906 (R) 907 The groups shown in the figure,

[0676] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms

[0677] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or

[0678] The group shown in formula (2) above,

[0679] R 901 ~R 907 With R 1 The definitions are the same.

[0680] Ar 2 Preferably, it is an aryl group with 6 to 50 cyclic carbons, whether substituted or unsubstituted, and more preferably, it is an aryl group with 6 to 30 cyclic carbons, whether substituted or unsubstituted.

[0681] Ar 2 Details of each group indicated, except for substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, are related to R. 1 The details of the corresponding functional groups recorded are the same, and the preferred functional groups are also the same.

[0682] Ar 2 Details of the substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms are shown in relation to Ar. 1 The details of the substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms are the same.

[0683] The unsubstituted heterocyclic group is preferably dibenzofuranyl, dibenzothiophenyl, or pyridyl.

[0684] Ar 2 Preferably, it is phenyl, biphenyl, naphthyl, or fluorenyl, and more preferably phenyl, biphenyl, or fluorenyl.

[0685] L 1 It is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms in a cyclic structure.

[0686] Examples of substituted or unsubstituted aryl groups with 6 to 30 carbon atoms in the cyclic group include: phenylene, biphenylene, terphenylene, naphthylene, anthraceneylene, benzene-anthracitel, phenanthreneylene, benzene-phenanthreneylene, phenenthenylene, alizarinylene, pentylenylene, pyreneylene, etc. Benzyl, benzo[a] It can be alkyl, phenylenetriene, fluorenetriene, or fluorenetriene, etc.

[0687] L 1 The substituted or unsubstituted arylene group with 6 to 30 carbon atoms is preferably phenylene, biphenylene, or naphthylene, and more preferably phenylene.

[0688] p is 0 or 1, (L) 1 0 refers to a single bond.

[0689] As one option, p is preferably 0. As another option, p is preferably 1.

[0690] The inventive compound represented by formula (1) is preferably represented by the following formula (4).

[0691] [Chemical Formula 29]

[0692]

[0693] In equation (4),

[0694] R 10 ~R 14 Each independently

[0695] hydrogen atom,

[0696] Halogen atoms,

[0697] Nitro,

[0698] cyano,

[0699] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0700] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0701] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0702] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0703] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0704] -O-(R 904 The groups shown in the figure,

[0705] -S-(R 905 The groups shown in the figure,

[0706] -N(R 906 (R) 907 The groups shown in the figure,

[0707] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0708] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0709] in,

[0710] Selected from R 10 ~R 14 One of them is a single bond bonded to *b, selected from R 10 ~R 14 The other one is a single bond that bonds with *c.

[0711] Y 1 X 1 ~X 8 、*a、HAr 2 Ar 1 Ar 2 L1 p and R 901 ~R 907 Same as the definition in equation (1).

[0712] R 10 ~R 14 Preferably, it is a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms in a cyclic ring, more preferably a hydrogen atom.

[0713] R 10 ~R 14 Details of each group indicated and for R 1 The details of the corresponding functional groups described are the same, and the preferred functional groups are also the same. Among them, dibenzofuran group is specified.

[0714] As a preferred option, R is preferred. 11 Or R 13 It is a single bond that bonds with *b.

[0715] In addition, R is preferred 11 Or R 13 It is a single bond that bonds with *c.

[0716] The inventive compound represented by formula (1) is preferably represented by formula (4A) or (4B) below, and more preferably by formula (4A) below.

[0717] [Chemical Formula 30]

[0718]

[0719] In equations (4A) and (4B),

[0720] R 20 ~R 24 and R 30 ~R 37 Each independently

[0721] hydrogen atom,

[0722] Halogen atoms,

[0723] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0724] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0725] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0726] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0727] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0728] -O-(R 904 The groups shown in the figure,

[0729] -S-(R 905 The group shown in the figure, or

[0730] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.

[0731] in,

[0732] Selected from R 30 ~R 37 One of them is a single bond that bonds with *d.

[0733] Y 1 X 1 ~X 8 、*a、Ar 1 Ar 2 L 1 p and R 901 ~R 907 Same as the definition in equation (1), *b, *c and R 10 ~R 14 Same as the definition in equation (4).

[0734] R 20 ~R 24 and R 30 ~R 37 Preferably, it is a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms in a cyclic ring, more preferably a hydrogen atom.

[0735] R 20 ~R 24 and R 30 ~R 37 Details of each group indicated and for R 1 The details of the corresponding functional groups described are the same, and the preferred functional groups are also the same. Among them, dibenzofuran group is specified.

[0736] As a preferred option, R is preferred. 11 Or R 13 It is a single bond that bonds with *b.

[0737] In addition, R is preferred 11 Or R 13 It is a single bond that bonds with *c.

[0738] As a preferred option, R is preferred. 31 Or R 32 As an alternative, R is preferred as a single bond that bonds with *d. 30 Or R 33 It is a single bond that bonds with *d.

[0739] The inventive compound represented by formula (1) is preferably represented by the following formula (5).

[0740] [Chemical Formula 31]

[0741]

[0742] In equation (5),

[0743] Y 1 X 1 ~X 8 、*a、HAr 2 Ar 1 Ar 2 L 1 And p is defined the same as in equation (1), R 10 R 12 and R 14 Same as the definition in equation (4).

[0744] The inventive compound represented by formula (1) is preferably represented by the following formula (4A-1).

[0745] [Chemical Formula 32]

[0746]

[0747] In equation (4A-1),

[0748] Y 1 X 1 ~X 8 、*a、Ar 1 Ar 2 L 1 And p is defined the same as in equation (1), R 10 R 12 and R 14 Same as the definition in equation (4), R 20 ~R 24 Same as the definition in equation (4A).

[0749] The inventive compound represented by formula (1) is preferably represented by the following formula (4A-1a).

[0750] [Chemical Formula 33]

[0751]

[0752] In equation (4A-1a),

[0753] Y 1 Ar 1 Ar 2 L 1And p is defined the same as in equation (1), R 10 R 12 and R 14 Same as the definition in equation (4), R 20 ~R 24 Same as the definition in equation (4A).

[0754] The inventive compound represented by formula (1) is preferably represented by the following formula (4A-1a-1) or (4A-1a-2).

[0755] [Chemical Formula 34]

[0756]

[0757] In formula (4A-1a-1) or (4A-1a-2),

[0758] Y 1 Ar 1 Ar 2 L 1 And p is defined the same as in equation (1), R 10 R 12 and R 14 Same as the definition in equation (4), R 20 ~R 24 Same as the definition in equation (4A).

[0759] The inventive compound represented by formula (1) is preferably represented by the following formula (4B-1).

[0760] [Chemical Formula 35]

[0761]

[0762] In equation (4B-1),

[0763] Y 1 X 1 ~X 8 、*a、AR 1 Ar 2 L 1 And p is defined the same as in equation (1), R 10 R 12 and R 14 Same as the definition in equation (4), *d and R 30 ~R 37 Same as the definition in equation (4B).

[0764] The inventive compound represented by formula (1) is preferably represented by the following formula (4B-1b).

[0765] [Chemical Formula 36]

[0766]

[0767] In equations (4B-1b) and (4B-2b),

[0768] Y 1 X 1 ~X 8 、*a、Ar 1 Ar 2 L 1 And p is defined the same as in equation (1), R 10 R 12 and R 14 Same as the definition in equation (4), *d and R 30 ~R 37 Same as the definition in equation (4B).

[0769] The inventive compound represented by formula (1) is preferably represented by the following formula (4B-1b-1) or (4B-1b-2).

[0770] [Chemical Formula 37]

[0771]

[0772] In equations (4B-1b-1) and (4B-1b-2),

[0773] Y 1 X 1 ~X 8 、*a、Ar 1 Ar 2 L 1 And p is defined the same as in equation (1), R 10 R 12 and R 14 Same as the definition in equation (4), *d and R 30 ~R 37 Same as the definition in equation (4B).

[0774] The inventive compound represented by formula (1) is preferably represented by the following formula (4B'-1) or (4B'-2).

[0775] [Chemical Formula 38]

[0776]

[0777] In equations (4B'-1) and (4B'-2),

[0778] Y 1 X 1 ~X 8 、*a、Ar 1 Ar2 L 1 And p is defined the same as in equation (1), R 10 ~R 14 Same as the definition in equation (4), *b, *c and R 30 ~R 31 Same as the definition in equation (4B).

[0779] As one aspect of the present invention.

[0780] (1-1)R 1 It can be a hydrogen atom.

[0781] In equations (4), (4A), (4B), (4B'-1), and (4B'-2), the R that is not a single bond bonded to *b and *c is... 10 ~R 14 Both can be hydrogen atoms.

[0782] In equations (5), (4A-1), (4A-1a), (4A-1a-1), (4A-1a-2), (4B-1), (4B-1b), (4B-1b-1), and (4B-1b-2), R... 10 R 12 and R 14 Both can be hydrogen atoms.

[0783] R in equations (4A), (4A-1), (4A-1a), (4A-1a-1), and (4A-1a-2) (1-4) 20 ~R 24 Both can be hydrogen atoms.

[0784] In equations (1-5), the R that is not bonded to *d is a single bond. 30 ~R 37 Both can be hydrogen atoms.

[0785] In equation (4B'-1) (1-6), R 30 and R 32 ~R 37 Both can be hydrogen atoms.

[0786] In equation (4B'-2) of (1-7), R 30 ~R 32 and R 34 ~R 37 Both can be hydrogen atoms.

[0787] As described above, the term "hydrogen atom" as used in this specification includes protium, deuterium, and tritium atoms. Therefore, the inventive compounds may contain naturally derived deuterium atoms.

[0788] Alternatively, deuterium atoms can be intentionally introduced into the inventive compound by using a portion or all of the raw material compound as a deuterated compound. Therefore, in one aspect of the present invention, the inventive compound contains at least one deuterium atom. That is, the inventive compound can be a compound represented by formula (1), wherein at least one of the hydrogen atoms contained in the compound is a deuterium atom.

[0789] Selected from L 2 The hydrogen atoms present in the substituted or unsubstituted phenylene;

[0790] R 1 Represents a hydrogen atom; R 1 The hydrogen atoms present in the substituted or unsubstituted alkyl, alkenyl, ynyl, cycloalkyl, aryl, and heterocyclic groups; R 1 -Si(R) represents 901 (R) 902 (R) 903 The group shown is -O-(R) 904 The group shown is -S-(R) 905 The group shown is -N(R) 906 (R) 907 The hydrogen atoms present in the group shown in the figure;

[0791] HAr 2 The hydrogen atom present in the substituted or unsubstituted aryl group;

[0792] AR 1 The hydrogen atom is represented by Ar. 1 The hydrogen atoms present in substituted or unsubstituted alkyl, alkenyl, ynyl, cycloalkyl, aryl, and heterocyclic groups; AR 1 -Si(R) represents 901 (R) 902 (R) 903 The group shown is -O-(R) 904 The group shown is -S-(R) 905 The group shown is -N(R) 906 (R) 907 The hydrogen atoms present in the group shown in the figure;

[0793] Ar 2 The hydrogen atom is represented by Ar. 2 The hydrogen atoms present in the substituted or unsubstituted alkyl, alkenyl, ynyl, cycloalkyl, aryl, and heterocyclic groups; Ar 1 -Si(R) represents 901(R) 902 (R) 903 The group shown is -O-(R) 904 The group shown is -S-(R) 905 The group shown is -N(R) 906 (R) 907 The hydrogen atoms present in the group shown in the figure;

[0794] R 901 ~R 907 Any one of the hydrogen atoms represented in R; 901 ~R 907 The hydrogen atom present in any of the substituted or unsubstituted alkyl, cycloalkyl, aryl, or heterocyclic groups represented in the text; and

[0795] L 1 The hydrogen atom present in the substituted or unsubstituted aryl group;

[0796] The hydrogen atoms in the pyrimidine ring explicitly stated in formula (1)

[0797] At least one hydrogen atom in it can be a deuterium atom.

[0798] The deuteration rate of the inventive compound depends on the deuteration rate of the raw material compound used. Even when using a raw material with a specified deuteration rate, it may contain a certain proportion of protium isotopes from natural sources. Therefore, the deuteration rate schemes of the inventive compounds shown below, relative to the proportions obtained by simply counting the number of deuterium atoms represented by the chemical formula, include the ratio of trace amounts of naturally sourced isotopes.

[0799] The deuteration rate of the inventive compound is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, and even more preferably 50% or more.

[0800] The inventive compound can be a mixture comprising a deuterated compound and an undeuterated compound, or a mixture of two or more compounds with different deuteration rates. The deuteration rate of such a mixture is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, even more preferably 10% or more, even more preferably 50% or more, and less than 100%.

[0801] Furthermore, the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the compound is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, and even more preferably 10% or more, and is less than 100%.

[0802] The details of the substituents (optional substituents) included in the definitions of the above formulas when expressed as "substituted or unsubstituted" are the same as those described in "substituents when expressed as "substituted or unsubstituted".

[0803] For the inventive compounds, those skilled in the art can easily manufacture them by referring to the synthetic examples described below and well-known synthetic methods.

[0804] The following examples of the inventive compounds are shown, but are not limited to the exemplified compounds below.

[0805] In the specific examples below, D represents a deuterium atom.

[0806] [Chemical Formula 39]

[0807]

[0808] [Chemical Formula 40]

[0809]

[0810] [Chemical Formula 41]

[0811]

[0812] [Chemical Formula 42]

[0813]

[0814] [Chemical Formula 43]

[0815]

[0816] [Chemical Formula 44]

[0817]

[0818] [Chemical Formula 45]

[0819]

[0820] [Chemical Formula 46]

[0821]

[0822] [Chemical Formula 47]

[0823]

[0824] [Chemical Formula 48]

[0825]

[0826] [Chemical Formula 49]

[0827]

[0828] [Chemical Formula 50]

[0829]

[0830] [Chemical Formula 51]

[0831]

[0832] [Chemical Formula 52]

[0833]

[0834] [Chemical Formula 53]

[0835]

[0836] [Chemical Formula 54]

[0837]

[0838] [Chemical Formula 55]

[0839]

[0840] [Chemical Formula 56]

[0841]

[0842] [Chemical Formula 57]

[0843]

[0844] [Chemical Formula 58]

[0845]

[0846] [Chemical Formula 59]

[0847]

[0848] [Chemical Formula 60]

[0849]

[0850] [Chemical Formula 61]

[0851]

[0852] [Chemical Formula 62]

[0853]

[0854] [Chemical Formula 63]

[0855]

[0856] [Chemical Formula 64]

[0857]

[0858] [Chemical Formula 65]

[0859]

[0860] [Chemical Formula 66]

[0861]

[0862] [Chemical Formula 67]

[0863]

[0864] [Chemical Formula 68]

[0865]

[0866] [Chemical Formula 69]

[0867]

[0868] [Chemical Formula 70]

[0869]

[0870] [Chemical Formula 71]

[0871]

[0872] [Chemical Formula 72]

[0873]

[0874] [Chemical Formula 73]

[0875]

[0876] [Chemical Formula 74]

[0877]

[0878] [Chemical Formula 75]

[0879]

[0880] [Chemical Formula 76]

[0881]

[0882] [Chemical Formula 77]

[0883]

[0884] [Chemical Formula 78]

[0885]

[0886] [Chemical Formula 79]

[0887]

[0888] [Chemical Formula 80]

[0889]

[0890] [Chemical Formula 81]

[0891]

[0892] [Chemical Formula 82]

[0893]

[0894] [Chemical Formula 83]

[0895]

[0896] [Chemical Formula 84]

[0897]

[0898] [Chemical Formula 85]

[0899]

[0900] [Chemical Formula 86]

[0901]

[0902] [Chemical Formula 87]

[0903]

[0904] [Chemical Formula 88]

[0905]

[0906] [Chemical Formula 89]

[0907]

[0908] [Chemical Formula 90]

[0909]

[0910] [Chemical Formula 91]

[0911]

[0912] [Chemical Formula 92]

[0913]

[0914] [Chemical Formula 93]

[0915]

[0916] [Chemical Formula 94]

[0917]

[0918] [Chemical Formula 95]

[0919]

[0920] [Chemical Formula 96]

[0921]

[0922] [Chemical Formula 97]

[0923]

[0924] [Chemical Formula 98]

[0925]

[0926] [Chemical Formula 99]

[0927]

[0928] [Chemical Formula 100]

[0929]

[0930] [Chemical Formula 101]

[0931]

[0932] [Chemical Formula 102]

[0933]

[0934] [Chemical Formula 103]

[0935]

[0936] [Chemical Formula 104]

[0937]

[0938] Materials for organic EL components

[0939] The organic EL element material of the present invention comprises the inventive compound. The content of the inventive compound in the organic EL element material is 1% by mass or more (including 100%), preferably 10% by mass or more (including 100%), more preferably 50% by mass or more (including 100%), further preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%). The organic EL element material of the present invention is useful in the manufacture of organic EL elements.

[0940] Organic EL components

[0941] 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 a light-emitting layer, and at least one layer of the organic layer includes the inventive compound.

[0942] Examples of organic layers comprising the inventive compound include hole transport regions (hole injection layers, hole transport layers, electron blocking layers, exciton blocking layers, etc.) disposed between the anode and the light-emitting layer, light-emitting layers, spacer layers, and electron transport regions (electron injection layers, electron transport layers, hole blocking layers, etc.) disposed between the cathode and the light-emitting layer, but are not limited thereto. The inventive compound is preferably a material used as an electron transport region of a fluorescent or phosphorescent EL element, more preferably a material used as an electron transport layer or a hole blocking layer, and particularly preferably a material used as a first electron transport layer, a second electron transport layer, or a hole blocking layer.

[0943] 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 type with a single light-emitting unit, or a series type with multiple light-emitting units. Preferably, it is a fluorescent light-emitting element. Here, "light-emitting unit" refers to the smallest unit containing an organic layer, wherein at least one layer is a light-emitting layer, and the injected holes and electrons emit light by recombination.

[0944] For example, the following are typical component configurations for a simple organic EL element.

[0945] (1) Anode / Light-emitting unit / Cathode

[0946] Alternatively, the aforementioned light-emitting unit can also be a multilayer type with multiple phosphorescent or fluorescent light-emitting layers. In this case, spacer layers may 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. A typical layer configuration of a simplified light-emitting unit is shown below. The layers within parentheses are optional.

[0947] (a)(hole injection layer / )hole transport layer / fluorescent layer / electron transport layer( / electron injection layer)

[0948] (b) (Hole injection layer / ) Hole transport layer / phosphorescent layer / electron transport layer ( / electron injection layer)

[0949] (c)(hole injection layer / )hole transport layer / first fluorescent layer / second fluorescent layer / electron transport layer( / electron injection layer)

[0950] (d)(Hole Injection Layer / )Hole Transport Layer / First Phosphorescent Layer / Second Phosphorescent Layer / Electron Transport Layer( / Electron Injection Layer)

[0951] (e)(hole injection layer / )hole transport layer / phosphorescent layer / spacer layer / fluorescent layer / electron transport layer( / electron injection layer)

[0952] (f)(Hole injection layer / )Hole transport layer / First phosphorescent layer / Second phosphorescent layer / Spacer layer / Fluorescent layer / Electron transport layer( / Electron injection layer)

[0953] (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)

[0954] (h)(hole injection layer / )hole transport layer / phosphorescent layer / spacer layer / first fluorescent layer / second fluorescent layer / electron transport layer( / electron injection layer)

[0955] (i)(hole injection layer / )hole transport layer / electron blocking layer / fluorescent layer / electron transport layer( / electron injection layer)

[0956] (j)(hole injection layer / )hole transport layer / electron blocking layer / phosphorescent layer / electron transport layer( / electron injection layer)

[0957] (k)(hole injection layer / )hole transport layer / exciton blocking layer / fluorescent layer / electron transport layer( / electron injection layer)

[0958] (l)(hole injection layer / )hole transport layer / exciton blocking layer / phosphorescent layer / electron transport layer( / electron injection layer)

[0959] (m)(hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent layer / electron transport layer( / electron injection layer)

[0960] (n)(hole injection layer / )first hole transport layer / second hole transport layer / phosphorescent layer / electron transport layer( / electron injection layer)

[0961] (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)

[0962] (p)(hole injection layer / ) 1st hole transport layer / 2nd hole transport layer / phosphorescent layer / 1st electron transport layer / 2nd electron transport layer ( / electron injection layer)

[0963] (q)(hole injection layer / )hole transport layer / fluorescent layer / hole blocking layer / electron transport layer( / electron injection layer)

[0964] (r)(hole injection layer / )hole transport layer / phosphorescent layer / hole blocking layer / electron transport layer( / electron injection layer)

[0965] (s)(hole injection layer / )hole transport layer / fluorescent layer / exciton blocking layer / electron transport layer( / electron injection layer)

[0966] (t)(hole injection layer / )hole transport layer / phosphorescent layer / exciton blocking layer / electron transport layer( / electron injection layer)

[0967] 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.

[0968] 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.

[0969] The following are typical component configurations for tandem organic EL elements.

[0970] (2) Anode / First Light-Emitting Unit / Intermediate Layer / Second Light-Emitting Unit / Cathode

[0971] 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.

[0972] 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.

[0973] 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) can be provided on the anode 3 side of the light-emitting layer 5, and a hole blocking layer (not shown) can 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.

[0974] Figure 2 This 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.

[0975] It should be noted that in this invention, the host material combined with the fluorescent dopant material (fluorescent emitting material) is called the fluorescent host material, and the host material combined with the phosphorescent dopant material is called the 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 the material that forms a phosphorescent emitting layer containing phosphorescent dopant, and does not mean that it cannot be used as a material to form a fluorescent emitting layer. The same applies to fluorescent hosts.

[0976] substrate

[0977] 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.

[0978] anode

[0979] 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).

[0980] 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 to 10 wt% zinc oxide relative to indium oxide, and indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5 to 5 wt% tungsten oxide and 0.1 to 1 wt% zinc oxide relative to indium oxide. Alternatively, they can be fabricated using vacuum evaporation, coating, inkjet printing, spin coating, and other methods.

[0981] 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.

[0982] 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), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and 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 alloys containing them 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.

[0983] Hole injection layer

[0984] A hole injection layer is a layer containing a material with high hole injection properties (hole injection material) and is formed between the anode and the light-emitting layer, or, if present, between the hole transport layer and the anode.

[0985] Other than the inventive compound, 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 as hole-injecting materials.

[0986] 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).

[0987] 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.

[0988] In addition, acceptor materials such as hexaazabenzophenanthrene (HAT) compounds represented by the following formula (K) are also preferred.

[0989] [Chemical Formula 105]

[0990]

[0991] (In the above formula, R) 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 R22 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-.

[0992] As R 27 Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, and cyclohexyl.

[0993] Hole transport layer

[0994] 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.

[0995] The hole transport layer can be a single-layer structure or a multi-layer structure containing two or more layers. For example, the hole transport layer can be a two-layer structure containing a first hole transport layer (anode side) and a second hole transport layer (cathode side). In one aspect of the invention, the hole transport layer of the single-layer structure is preferably adjacent to the light-emitting layer. Furthermore, it is preferable that 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 adjacent to the light-emitting layer. In another aspect 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 closest to the light-emitting layer in the multi-layer structure.

[0996] As hole transport layer materials, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used, for example.

[0997] 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-dimethyl]... [fluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4”-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The above compounds have 10 -6 cm 2Hole mobility above / Vs.

[0998] 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).

[0999] Examples of anthracene derivatives include 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (abbreviated as t-BuDNA), 9,10-bis(2-naphthyl)anthracene (abbreviated as DNA), and 9,10-diphenylanthracene (abbreviated as DPAnnth).

[1000] Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) can also be used.

[1001] Among them, any compound whose hole transport capability is higher than its electron transport capability can use compounds other than those mentioned above.

[1002] dopant material of the light-emitting layer

[1003] 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.

[1004] 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.

[1005] 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.

[1006] 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).

[1007] In one embodiment of the present invention, the light-emitting layer preferably comprises a fluorescent light-emitting material (fluorescent dopant material).

[1008] As blue phosphorescent materials that can be used in the luminescent layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes can be used. 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).

[1009] As a green phosphorescent material that can be used in the light-emitting layer, iridium complexes can be 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)).

[1010] 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.

[1011] 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)eupium(III) (abbreviated as Eu(DBM)3(Phen)), and tri[1-(2-thiophenecarboxyl)-3,3,3-trifluoroacetone](monophenanthrene)eupium(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).

[1012] In one aspect of the present invention, the light-emitting layer preferably comprises a phosphorescent material (phosphorescent dopant material).

[1013] The main material of the light-emitting layer

[1014] 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.

[1015] As the main material, for example, using

[1016] (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes;

[1017] (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives;

[1018] (3) Carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or Derivatives and other fused aromatic compounds,

[1019] (4) Aromatic amine compounds such as triarylamine derivatives or fused polycyclic aromatic amine derivatives.

[1020] 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;

[1021] 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);

[1022] 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'-Banthracite (BANT), 9,9'-(Index-3,3'-diyl)diphenanthrene (DPNS), 9,9'-(Index-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

[1023] 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) can be used as the main material.

[1024] In particular, in the case of blue fluorescent elements, the following anthracene compounds are preferred as the main material.

[1025] [Chemical Formula 106]

[1026]

[1027] [Chemical Formula 107]

[1028]

[1029] [Chemical Formula 108]

[1030]

[1031] Electron transport layer

[1032] An electron transport layer is a layer containing a material with high electron transport properties (electron transport material) and is 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. The inventive compounds can be used alone or in combination with compounds described later in the electron transport layer.

[1033] The electron transport layer can be a single-layer structure or a multi-layer structure containing two or more layers. For example, the electron transport layer can be a two-layer structure containing a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one aspect 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 aspect 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.

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

[1035] In one embodiment of the invention, the inventive compound is preferably contained only in the first electron transport layer; in another embodiment, the inventive compound is preferably contained only in the second electron transport layer; and in yet another embodiment, the inventive compound is contained in both the first and second electron transport layers.

[1036] In one aspect of the invention, the inventive compound contained in one or both of the first and second electron transport layers is preferably protium from the viewpoint of manufacturing cost.

[1037] The aforementioned protium refers to an inventive compound in which all hydrogen atoms are protium atoms.

[1038] Therefore, the present invention includes an organic EL element comprising one or both of the first and second electron transport layers described above, which are substantially composed solely of the inventive compound formed by protium. "Substantially composed solely of protium" means that the protium content is 90 mol% or more, preferably 95 mol% or more, and more preferably 99 mol% or more (each including 100%), relative to the total amount of the inventive compound.

[1039] For example, electron transport layers can use

[1040] (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes;

[1041] (2) Imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives, and other heteroaromatic compounds.

[1042] (3) Polymer compounds.

[1043] 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).

[1044] 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)zirconia (abbreviated as BzOs).

[1045] 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).

[1046] 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.

[1047] Electron injection layer

[1048] 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.

[1049] 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.

[1050] Alternatively, the electron injection layer can be a composite material formed by mixing an organic compound and 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.

[1051] cathode

[1052] 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) and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb) and alloys containing them.

[1053] 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.

[1054] 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.

[1055] Insulation layer

[1056] 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.

[1057] 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.

[1058] Spacer layer

[1059] 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.

[1060] Since the spacer layer is disposed between the light-emitting layers, it is preferably made of a material that has 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 used as examples of materials for the spacer layer.

[1061] Barrier layer

[1062] Electron blocking layers, hole blocking layers, exciton blocking layers, and other blocking layers can also be disposed 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.

[1063] In one embodiment of the invention, it is preferred that the electron transport region includes a hole-blocking layer on the cathode side, the hole-blocking layer comprising the inventive compound. Furthermore, it is preferable that the hole-blocking layer is adjacent to the light-emitting layer.

[1064] 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 using known coating methods based on solutions of the compound forming the layer, such as dip coating, spin coating, casting, rod coating, and roll coating.

[1065] 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, the thickness is usually 5nm to 10μm, and more preferably 10nm to 0.2μm.

[1066] 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.

[1067] Example

[1068] The present invention will be further described in detail below using examples, but the present invention is not limited to the following examples.

[1069] The inventive compound used in the manufacture of the organic EL element in Example 1

[1070] [Chemical Formula 109]

[1071]

[1072] The comparative compounds used in the manufacture of the organic EL elements of Comparative Examples 1 and 2

[1073] [Chemical Formula 110]

[1074]

[1075] The inventive compounds used in the manufacture of organic EL elements in Examples 2-14

[1076] [Chemical Formula 111]

[1077]

[1078] Other compounds used in the manufacture of the organic EL elements of Example 1 and Comparative Example 1

[1079] [Chemical Formula 112]

[1080]

[1081] Other compounds used in the manufacture of organic EL elements in Examples 2-14 and Comparative Example 2

[1082] [Chemical Formula 113]

[1083]

[1084] Fabrication of organic EL components

[1085] Example 1

[1086] 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.

[1087] The cleaned glass substrate with the ITO 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 (HT-1:HI-1) was 97:3.

[1088] Next, compound HT-1 was deposited on the hole injection layer to form the first hole transport layer with a thickness of 80 nm.

[1089] Next, EBL-1 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 5 nm.

[1090] Next, compound BH-1 (the host material) and compound BD-1 (the dopant material) were co-deposited on the second hole transport layer to form a light-emitting layer with a thickness of 20 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 99:1.

[1091] Next, compound 1 is deposited on the light-emitting layer to form a first electron transport layer with a thickness of 5 nm.

[1092] Next, compounds ET-1 and Liq were co-deposited on the first electron transport layer to form a second electron transport layer with a thickness of 25 nm. The mass ratio of compound ET-1 to Liq (ET-1:Liq) was 50:50.

[1093] Next, Yb was deposited on the second electron transport layer to form an electron injection electrode with a film thickness of 1 nm.

[1094] Then, metallic Al was deposited on the electron-injecting electrode to form a metal cathode with a film thickness of 80 nm.

[1095] The following shows the layer configuration of the organic EL element of Example 1 thus obtained.

[1096] ITO(130) / HT-1∶HI-1=97∶3(10) / HT-1(80) / EBL-1(5) / BH-1∶BD-1=99∶1(20) / compound1(5) / ET-1∶Liq=50∶50(25) / Yb(1) / Al(80)

[1097] In the above layer composition, the numbers in parentheses are film thicknesses (nm), expressed as mass ratios.

[1098] Evaluation of Organic EL Devices: Measurement of External Quantum Efficiency (EQE)

[1099] Each organic EL element was subjected to a current density of 1 mA / cm² at room temperature. 2 A DC constant current drive was used. The luminance was measured using a luminance meter (Minolta CS-1000 spectroradiometer), and the external quantum efficiency (%) was calculated based on the results. The results are shown in Table 1.

[1100] Comparative Example 1

[1101] The first electron transport layer material was changed to the compounds shown in Table 1 below, and each organic EL element was fabricated in the same manner as in Example 1, and the external quantum efficiency (EQE) was measured. The results are shown in Table 1.

[1102] [Table 1]

[1103] Table 1

[1104]

[1105] Example 2

[1106] 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.

[1107] The cleaned glass substrate with the ITO transparent electrode was mounted on the substrate holder of a vacuum evaporation apparatus. First, compound HT-2 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-2 to compound HI-1 (HT-2:HI-1) was 97:3.

[1108] Next, compound HT-2 was deposited on the hole injection layer to form the first hole transport layer with a thickness of 80 nm.

[1109] Next, EBL-1 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 5 nm.

[1110] Next, compound BH-2 (host material) 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 20 nm. The mass ratio of compound BH-2 to compound BD-1 (BH-2:BD-1) was 99:1.

[1111] Next, compound 1 was deposited on the light-emitting layer to form a first electron transport layer with a thickness of 5 nm.

[1112] Next, compounds ET-1 and Liq were co-deposited on the first electron transport layer to form a second electron transport layer with a thickness of 25 nm. The mass ratio of compound ET-1 to Liq (ET-1:Liq) was 50:50.

[1113] Next, Yb was deposited on the second electron transport layer to form an electron injection electrode with a film thickness of 1 nm.

[1114] Then, metallic Al was deposited on the electron-injecting electrode to form a metal cathode with a film thickness of 80 nm.

[1115] The following shows the layer configuration of the organic EL element of Example 2 obtained in this way.

[1116] ITO(130) / HT-2∶HI-1=97∶3(10) / HT-2(80) / EBL-1(5) / BH-2∶BD-1=99∶1(20) / compound1(5) / ET-1∶Liq=50∶50(25) / Yb(1) / Al(80)

[1117] In the above layer composition, the numbers in parentheses are film thicknesses (nm), expressed as mass ratios.

[1118] In addition, the external quantum efficiency (EQE) of the obtained organic EL element was measured. The results are shown in Table 2.

[1119] Examples 3-14 and Comparative Example 2

[1120] The first electron transport layer material was changed to the compounds shown in Table 2 below, and each organic EL element was fabricated in the same manner as in Example 2. The external quantum efficiency (EQE) was measured. The results are shown in Table 2.

[1121] [Table 2]

[1122] Table 2

[1123]

[1124] As can be seen from the results in Tables 1 and 2, the compounds of the present invention provide more efficient organic EL elements compared to the comparative compounds.

[1125] Compounds 1-26 synthesized in Synthetic Examples 1-26

[1126] [Chemical Formula 114]

[1127]

[1128] [Chemical Formula 115]

[1129]

[1130] Synthesis Example 1: Synthesis of Compound 1

[1131] [Chemical Formula 116]

[1132]

[1133] (1-1) Synthesis of intermediate A

[1134] 1-(9,9-dimethyl-9H-fluorene-2-yl)acetone (18 g), 3-bromo-5-chlorobenzaldehyde (18 g), sodium methoxide (5 M methanol solution, 15 mL), and ethanol (190 mL) were mixed and stirred at room temperature for 2 hours. After adding water, the precipitated solid was filtered off, washed successively with water and ethanol, and dried under reduced pressure to obtain intermediate A (35 g) as a white solid.

[1135] (1-2) Synthesis of intermediate B

[1136] Intermediate A (34 g), benzalkonium hydrochloride (12 g), sodium methoxide (5 M methanol solution, 18 mL), and ethanol (190 mL) were mixed and refluxed for 3.5 hours. After the reaction was completed, the precipitate was filtered off and purified by silica gel column chromatography to obtain intermediate B (15 g, yield 34% in the two steps) as a white solid.

[1137] (1-3) Synthesis of intermediate C

[1138] Intermediate B (14 g) and 2-dibenzofuranylboronic acid (6.0 g) were dissolved in 1,2-dimethoxyethane (260 mL), and tetrakis(triphenylphosphine)palladium (0) (1.2 g) and sodium carbonate aqueous solution (2 M, 39 mL) were added. The mixture was heated under reflux for 6.5 hours. After the reaction was completed, the reaction solution was cooled to room temperature and extracted with toluene. The resulting organic layer was washed with saturated brine and dried with magnesium sulfate, and the solvent was removed by vacuum distillation. The residue was purified by silica gel column chromatography and suspension washing to give intermediate C (15 g, 93% yield) as a white solid.

[1139] (1-4) Synthesis of Compound 1

[1140] 1,2-Dimethoxyethane (56 mL) was added to intermediate C (7.0 g) and phenylboronic acid (1.5 g) and stirred. PdCl₂(Amphos)₂ (0.32 g) and sodium carbonate aqueous solution (2 M, 17 mL) were then added, and the mixture was stirred at 80 °C for 6.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature and extracted with toluene. The resulting organic layer was washed with saturated brine and dried with magnesium sulfate, and the solvent was removed by vacuum distillation. The residue was purified by silica gel column chromatography and suspension washing to give a white solid (7.3 g, 98% yield).

[1141] The mass spectrometry analysis of the obtained white solid showed an m / e ratio of 667, indicating that it was compound 1.

[1142] Synthesis Example 2: Synthesis of Compound 2

[1143] [Chemical Formula 117]

[1144]

[1145] (2-1) Synthesis of Compound 2

[1146] In Synthesis Example 1 (1-4), 3-biphenylboronic acid was used instead of phenylboronic acid, and the same method was used to synthesize the same substance, yielding a white solid (4.3 g, 73% yield).

[1147] The mass spectrometry analysis of the obtained white solid showed an m / e ratio of 743, indicating that it was compound 2.

[1148] Synthesis Example 3: Synthesis of Compound 3

[1149] [Chemical Formula 118]

[1150]

[1151] (3-1) Synthesis of Compound 3

[1152] In Synthesis Example 1 (1-4), 4-biphenylboronic acid was used instead of phenylboronic acid, and the same method was used to synthesize the same substance, yielding a white solid (4.6 g, yield 82%).

[1153] The mass spectrometry analysis of the obtained white solid showed an m / e ratio of 743, indicating that it was compound 3.

[1154] Synthesis Example 4: Synthesis of Compound 4

[1155] [Chemical Formula 119]

[1156]

[1157] (4-1) Synthesis of Compound 4

[1158] In Synthesis Example 1 (1-4), 1-naphthylboronic acid was used instead of phenylboronic acid, and the same method was used to synthesize the same substance, yielding a white solid (5.1 g, 79% yield).

[1159] The obtained white solid was analyzed by mass spectrometry, and the m / e ratio was 717, indicating that it was compound 4.

[1160] Synthesis Example 5: Synthesis of Compound 5

[1161] [Chemical Formula 120]

[1162]

[1163] (5-1) Synthesis of Compound 5

[1164] In Synthesis Example 1 (1-4), 2-naphthylboronic acid was used instead of phenylboronic acid, and the same method was used to synthesize the same substance, yielding a white solid (4.6 g, 73% yield).

[1165] The obtained white solid was analyzed by mass spectrometry, and the m / e ratio was 717, indicating that it was compound 5.

[1166] Synthesis Example 6: Synthesis of Compound 6

[1167] [Chemical Formula 121]

[1168]

[1169] (6-1) Synthesis of intermediate D

[1170] In Synthesis Example 1 (1-3), 2-dibenzothiophene boric acid was used instead of 2-dibenzofuranylboronic acid, and the same method was used to synthesize intermediate D (5.2 g, 87% yield) as a white solid.

[1171] (6-2) Synthesis of Compound 6

[1172] In (1-4) of Synthesis Example 1, intermediate D was used instead of intermediate C, and the same method was used to synthesize the other components, yielding a white solid (5.1 g, 92% yield).

[1173] The mass spectrometry analysis of the obtained white solid showed an m / e ratio of 683, identifying it as compound 6.

[1174] Synthesis Example 7: Synthesis of Compound 7

[1175] [Chemical Formula 122]

[1176]

[1177] (7-1) Synthesis of intermediate E

[1178] In Synthesis Example 1 (1-3), phenylboronic acid was used instead of 2-dibenzofuranylboronic acid, and the same method was used to synthesize intermediate E (8.2 g, 73% yield) as a white solid.

[1179] (7-2) Synthesis of Compound 7

[1180] In Synthesis Example 1 (1-4), intermediate E was used instead of intermediate C, and 4-dibenzothiophene boric acid was used instead of phenylboronic acid. Otherwise, the same method was used to synthesize the same substance, yielding a white solid (4.6 g, yield 86%).

[1181] The obtained white solid was analyzed by mass spectrometry, and the m / e ratio was 683, indicating that it was compound 7.

[1182] Synthesis Example 8: Synthesis of Compound 8

[1183] [Chemical Formula 123]

[1184]

[1185] (8-1) Synthesis of Compound 8

[1186] In Synthesis Example 1 (1-4), intermediate F was used instead of intermediate C, and 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborphane-2-yl)[1,1'-biphenyl]-3-yl]dibenzofuran was used instead of phenylboronic acid. Otherwise, the same method was used to synthesize the same substance, yielding a white solid (4.6 g, yield 86%).

[1187] The mass spectrometry analysis of the obtained white solid showed an m / e ratio of 667, identifying it as compound 8.

[1188] Synthesis Example 9: Synthesis of Compound 9

[1189] [Chemical Formula 124]

[1190]

[1191] (9-1) Synthesis of Compound 9

[1192] In Synthetic Example 1 (1-4), 4-chloro-6-[3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl]-2-phenylpyrimidine was used instead of intermediate C, and 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborphane-2-yl)[1,1'-biphenyl]-3-yl]dibenzothiophene was used instead of phenylboronic acid. Otherwise, the same method was used to synthesize a white solid (4.2 g, 78% yield).

[1193] The obtained white solid was analyzed by mass spectrometry, and the m / e ratio was 759, indicating that it was compound 9.

[1194] Synthesis Example 10: Synthesis of Compound 10

[1195] [Chemical Formula 125]

[1196]

[1197] (10-1) Synthesis of intermediate G

[1198] In Synthetic Example 1 (1-3), 4,6-dichloro-2-phenylpyrimidine was used instead of intermediate B, 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaboron-2-yl)[1,1'-biphenyl]-3-yl]dibenzofuran was used instead of 2-dibenzofuranylboronic acid, and toluene was used instead of 1,2-dimethoxyethane. Otherwise, the same method was used to synthesize intermediate G (4.6 g, 86% yield) as a white solid.

[1199] (10-2) Synthesis of Compound 10

[1200] In Synthesis Example 1 (1-4), intermediate G was used instead of intermediate C, and (9,9-dimethyl-9H-fluorene-3-yl)boronic acid was used instead of phenylboronic acid. Otherwise, the same method was used to synthesize the same substance, yielding a white solid (3.6 g, yield 65%).

[1201] The mass spectrometry analysis of the obtained white solid showed an m / e ratio of 667, indicating it was compound 10.

[1202] Synthesis Example 11: Synthesis of Compound 11

[1203] [Chemical Formula 126]

[1204]

[1205] (11-1) Synthesis of Compound 11

[1206] In Synthesis Example 1 (1-4), intermediate G obtained in Synthesis Example 10 was used instead of intermediate C, and 2-(9,9-dimethyl-9H-fluoren-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborhecyclopentane was used instead of phenylboronic acid. Otherwise, the same method was used to synthesize the same substance, and a white solid (4.8 g, yield 71%) was obtained.

[1207] The mass spectrometry analysis of the obtained white solid showed an m / e ratio of 667, identifying it as compound 11.

[1208] Synthesis Example 12: Synthesis of Compound 12

[1209] [Chemical Formula 127]

[1210]

[1211] (12-1) Synthesis of intermediate H

[1212] In Synthetic Example 1 (1-3), 4,6-dichloro-2-phenylpyrimidine was used instead of intermediate B, 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaboron-2-yl)[1,1'-biphenyl]-3-yl]dibenzothiophene was used instead of 2-dibenzofuranylboronic acid, and toluene was used instead of 1,2-dimethoxyethane. Otherwise, the same method was used to synthesize intermediate H (5.8 g, yield 64%) as a white solid.

[1213] (12-2) Synthesis of Compound 12

[1214] In Synthesis Example 1 (1-4), intermediate H was used instead of intermediate C, and 2-(9,9-dimethyl-9H-fluoren-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborhecyclopentane was used instead of phenylboronic acid. Otherwise, the same method was used to synthesize the same substance, yielding a white solid (3.3 g, yield 68%).

[1215] The obtained white solid was analyzed by mass spectrometry, and the m / e ratio was 683, indicating that it was compound 12.

[1216] Synthesis Example 13: Synthesis of Compound 13

[1217] [Chemical Formula 128]

[1218]

[1219] (13-1) Synthesis of Compound 13

[1220] In Synthesis Example 1 (1-4), intermediate I was used instead of intermediate C, and 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborphane-2-yl)[1,1'-biphenyl]-3-yl]dibenzofuran was used instead of phenylboronic acid. Otherwise, the same method was used to synthesize the same substance, yielding a white solid (4.2 g, 72% yield).

[1221] The obtained white solid was analyzed by mass spectrometry, and the m / e ratio was 791, indicating that it was compound 13.

[1222] Synthesis Example 14: Synthesis of Compound 14

[1223] [Chemical Formula 129]

[1224]

[1225] (14-1) Synthesis of Compound 14

[1226] In Synthesis Example 1 (1-4), intermediate J was used instead of intermediate C, and 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborphane-2-yl)[1,1'-biphenyl]-3-yl]dibenzofuran was used instead of phenylboronic acid. Otherwise, the same method was used to synthesize the same substance, yielding a white solid (2.3 g, yield 63%).

[1227] The mass spectrometry analysis of the obtained white solid showed an m / e ratio of 791, identifying it as compound 14.

[1228] Synthesis Example 15: Synthesis of Compound 15

[1229] [Chemical Formula 130]

[1230]

[1231] (15-1) Synthesis of Compound 15

[1232] In Synthesis Example 1 (1-4), intermediate K was used instead of intermediate C, and 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborphane-2-yl)[1,1'-biphenyl]-3-yl]dibenzofuran was used instead of phenylboronic acid. Otherwise, the same method was used to synthesize the same substance, yielding a white solid (4.8 g, 78% yield).

[1233] The obtained white solid was analyzed by mass spectrometry, and the m / e ratio was 791, indicating that it was compound 15.

[1234] Synthesis Example 16: Synthesis of Compound 16

[1235] [Chemical Formula 131]

[1236]

[1237] (16-1) Synthesis of intermediate L

[1238] In (1-3) of Synthesis Example 1, 2-(3-bromo-5-chlorophenyl)naphthalene was used instead of intermediate B, and the same method was used to synthesize intermediate L (11 g, 73% yield) as a white solid.

[1239] (16-2) Synthesis of intermediate M

[1240] 1,4-Dioxane (130 mL) was added to intermediate L (10 g), bis(pinacol)diboron (7.5 g), Pd2(dba)3 (0.45 g), XPhos (0.94 g), and potassium acetate (4.9 g). Argon gas was then introduced into the suspension for 5 minutes. The mixture was heated at 100 °C for 4 hours with stirring under an argon atmosphere. The reaction solution was subjected to solvent distillation, toluene and water were added, and the organic phase was separated. The residue obtained after concentrating the organic phase was subjected to column chromatography to give intermediate M (8.6 g, 70% yield) as a white solid.

[1241] (16-3) Synthesis of Compound 16

[1242] In Synthesis Example 1 (1-4), intermediate M was used instead of phenylboronic acid, and 4-[1,1'-biphenyl]-3-yl-6-chloro-2-phenylpyrimidine was used instead of intermediate C. Otherwise, the same method was used to synthesize the same substance, yielding a white solid (3.6 g, yield 64%).

[1243] The mass spectrometry analysis of the obtained white solid showed an m / e ratio of 677, identifying it as compound 16.

[1244] Synthesis Example 17: Synthesis of Compound 17

[1245] [Chemical Formula 132]

[1246]

[1247] (17-1) Synthesis of intermediate N

[1248] In Synthesis Example 1 (1-3), 1-(3-bromo-5-chlorophenyl)naphthalene was used instead of intermediate B, and the same method was used to synthesize intermediate L (9 g, yield 68%) as a white solid.

[1249] (17-2) Synthesis of intermediate P

[1250] In synthesis example 16 (16-2), intermediate N was used instead of intermediate L, and the same method was used to synthesize intermediate P as a white solid (7.2 g, yield 65%).

[1251] (17-3) Synthesis of Compound 17

[1252] In Synthesis Example 1 (1-4), intermediate P was used instead of phenylboronic acid, and 4-[1,1'-biphenyl]-4-yl-6-chloro-2-phenylpyrimidine was used instead of intermediate C. Otherwise, the same method was used to synthesize the same substance, yielding a white solid (3.2 g, yield 67%).

[1253] The obtained white solid was analyzed by mass spectrometry, and the m / e ratio was 677, indicating that it was compound 17.

[1254] Synthesis Example 18: Synthesis of Compound 18

[1255] [Chemical Formula 133]

[1256]

[1257] (18-1) Synthesis of intermediate Q

[1258] In Synthetic Examples 1 (1-3), 4,6-dichloro-2-phenylpyrimidine was used instead of intermediate B, 4,4,5,5-tetramethyl-2-(9-methyl-9-phenyl-9H-fluoren-2-yl)-1,3,2-dioxaborane was used instead of 2-dibenzofuranylboronic acid, and toluene was used instead of 1,2-dimethoxyethane. Otherwise, the same method was used to synthesize intermediate Q (6.8 g, 78% yield) as a white solid.

[1259] (18-2) Synthesis of Compound 18

[1260] In Synthesis Example 1 (1-4), intermediate Q was used instead of intermediate C, and 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborphane-2-yl)[1,1'-biphenyl]-3-yl]dibenzofuran was used instead of phenylboronic acid. Otherwise, the same method was used to synthesize the same substance, yielding a white solid (6.1 g, 81% yield).

[1261] The mass spectrometry analysis of the obtained white solid showed an m / e ratio of 729, identifying it as compound 18.

[1262] Synthesis Example 19: Synthesis of Compound 19

[1263] [Chemical Formula 134]

[1264]

[1265] (19-1) Synthesis of intermediate R

[1266] In Synthetic Examples 1 (1-3), 4,6-dichloro-2-phenylpyrimidine was used instead of intermediate B, 4,4,5,5-tetramethyl-2-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]-1,3,2-dioxaborane was used instead of 2-dibenzofuranylboronic acid, and toluene was used instead of 1,2-dimethoxyethane. Otherwise, the same method was used to synthesize intermediate R (5.5 g, yield 63%) as a white solid.

[1267] (19-2) Synthesis of Compound 19

[1268] In Synthesis Example 1 (1-4), intermediate R was used instead of intermediate C, and 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborphane-2-yl)[1,1'-biphenyl]-3-yl]dibenzofuran was used instead of phenylboronic acid. Otherwise, the same method was used to synthesize the same substance, yielding a white solid (5.0 g, yield 59%).

[1269] The mass spectrometry analysis of the obtained white solid showed an m / e ratio of 791, identifying it as compound 19.

[1270] Synthesis Example 20: Synthesis of Compound 20

[1271] [Chemical Formula 135]

[1272]

[1273] (20-1) Synthesis of intermediate S

[1274] In Synthetic Example 1 (1-3), 4,6-dichloro-2-phenylpyrimidine was used instead of intermediate B, 2-(9,9-dimethyl-9H-fluoren-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane was used instead of 2-dibenzofuranylboronic acid, and toluene was used instead of 1,2-dimethoxyethane. Otherwise, the same method was used to synthesize intermediate S (4.5 g, yield 53%) as a white solid.

[1275] (20-2) Synthesis of Compound 20

[1276] In Synthesis Example 1 (1-4), intermediate S was used instead of intermediate C, and 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborphane-2-yl)[1,1'-biphenyl]-3-yl]dibenzofuran was used instead of phenylboronic acid. Otherwise, the same method was used to synthesize the same substance, yielding a white solid (5.0 g, 73% yield).

[1277] The mass spectrometry analysis of the obtained white solid showed an m / e ratio of 667, identifying it as compound 20.

[1278] Synthesis Example 21: Synthesis of Compound 21

[1279] [Chemical Formula 136]

[1280]

[1281] (21-1) Synthesis of intermediate T

[1282] In Synthetic Example 1 (1-3), 4,6-dichloro-2-phenylpyrimidine was used instead of intermediate B, 2-(9,9-dimethyl-9H-fluoren-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaboranecyclopentane was used instead of 2-dibenzofuranylboronic acid, and toluene was used instead of 1,2-dimethoxyethane. Otherwise, the same method was used to synthesize intermediate T (5.8 g, 70% yield) as a white solid.

[1283] (21-2) Synthesis of Compound 21

[1284] In Synthesis Example 1 (1-4), intermediate T was used instead of intermediate C, and 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborphane-2-yl)[1,1'-biphenyl]-3-yl]dibenzofuran was used instead of phenylboronic acid. Otherwise, the same method was used to synthesize the same substance, yielding a white solid (3.8 g, 78% yield).

[1285] The mass spectrometry analysis of the obtained white solid showed an m / e ratio of 667, identifying it as compound 21.

[1286] Synthesis Example 22: Synthesis of Compound 22

[1287] [Chemical Formula 137]

[1288]

[1289] In Synthesis Example 1 (1-4), intermediate U was used instead of intermediate C, and 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborphane-2-yl)[1,1'-biphenyl]-3-yl]dibenzofuran was used instead of phenylboronic acid. Otherwise, the same method was used to synthesize the same substance, yielding a white solid (4.9 g, 84% yield).

[1290] The mass spectrometry analysis of the obtained white solid showed an m / e ratio of 677, identifying it as compound 22.

[1291] Synthesis Example 23: Synthesis of Compound 23

[1292] [Chemical Formula 138]

[1293]

[1294] (23-1) Synthesis of intermediate V

[1295] In Synthetic Example 1 (1-3), 4,6-dichloro-2-phenylpyrimidine was used instead of intermediate B, 2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborphane-2-yl)phenyl]dibenzofuran was used instead of 2-dibenzofuranylboronic acid, and toluene was used instead of 1,2-dimethoxyethane. Otherwise, the same method was used to synthesize intermediate V (3.8 g, 73% yield) as a white solid.

[1296] (23-2) Synthesis of compound 23

[1297] In Synthesis Example 1 (1-4), intermediate V was used instead of intermediate C, and 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborphane-2-yl)[1,1'-biphenyl]-3-yl]dibenzofuran was used instead of phenylboronic acid. Otherwise, the same method was used to synthesize the same substance, yielding a white solid (5.2 g, 83% yield).

[1298] The mass spectrometry analysis of the obtained white solid showed an m / e ratio of 717, identifying it as compound 23.

[1299] Synthesis Example 24: Synthesis of Compound 24

[1300] [Chemical Formula 139]

[1301]

[1302] In Synthesis Example 1 (1-4), [2-(1,1-dimethylethyl)phenyl]boronic acid was used instead of phenylboronic acid, and the same method was used to synthesize the same substance, yielding a white solid (4.1 g, yield 63%).

[1303] The mass spectrometry analysis of the obtained white solid showed an m / e ratio of 723, identifying it as compound 24.

[1304] Synthesis Example 25: Synthesis of Compound 25

[1305] [Chemical Formula 140]

[1306]

[1307] In Synthesis Example 1 (1-4), intermediate W was used instead of intermediate C, and benzo[b]naphtho[1,2-d]furan-9-boronic acid was used instead of phenylboronic acid. Otherwise, the same method was used to synthesize the same substance, yielding a white solid (3.1 g, 71% yield).

[1308] The mass spectrometry analysis of the obtained white solid showed an m / e ratio of 601, identifying it as compound 25.

[1309] Synthesis Example 26: Synthesis of Compound 26

[1310] [Chemical Formula 141]

[1311]

[1312] In (1-4) of Synthetic Example 1, (phenyl-2,3,4,5,6-d)boronic acid was used instead of phenylboronic acid, and the same method was used to synthesize the same substance, yielding a white solid (2.3 g, 63% yield).

[1313] The mass spectrometry analysis of the obtained white solid showed an m / e ratio of 672, identifying it as compound 26.

[1314] Symbol Explanation

[1315] 1.11 Organic EL elements

[1316] 2 substrate

[1317] 3 Anode

[1318] 4 Cathode

[1319] 5. Light-emitting layer

[1320] 6. Hole transport region (hole transport layer)

[1321] 6a Hole injection layer

[1322] 6b Hole Transport Layer 1

[1323] 6c Hole transport layer 2

[1324] 7. Electron transport region (electron transport layer)

[1325] 7a First electron transport layer

[1326] 7b Second electron transport layer

[1327] 10, 20 light-emitting units

Claims

1. The compound represented by the following formula (1), In equation (1), A is the group shown in formula (2). In equation (2), HAr 1 The group represented by formula (3), m is an integer from 1 to 4. n is an integer from 1 to 4. m + n is an integer from 2 to 5. When m+n is 2, L 2 It is a trivalent linker group. When m+n is 3 to 5, L 2 It consists of tetravalent to hexavalent linking groups, with multiple HAr 1 Multiple HArs can be selected from each other, either identical or different. 2 Choose either the same or different from each other. The linking group is a substituted or unsubstituted benzene ring. in, When the benzene ring is described as "substituted or unsubstituted", the substituent is selected from the group consisting of unsubstituted alkyl groups having 1 to 18 carbon atoms, unsubstituted cycloalkyl groups having 3 to 6 carbon atoms, and unsubstituted aryl groups having 6 to 18 carbon atoms. * indicates the bonding position with the central pyrimidine ring. In equation (3), Y 1 It consists of oxygen or sulfur atoms. X 1 ~X 8 Each independently for CR 1 , R 1 for hydrogen atom, or Substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, in, Selected from X 1 ~X 8 One of them is a carbon atom bonded to *a. ** indicates that it is related to L 2 The bonding position, HAr 2 For substituted or unsubstituted aryl groups with 6 to 12 carbon atoms in a cyclic structure, Wherein, the HAr 2 When the expression "substituted or unsubstituted" is used, the substituent is selected from the group consisting of unsubstituted alkyl groups having 1 to 18 carbon atoms, unsubstituted cycloalkyl groups having 3 to 6 carbon atoms, and unsubstituted aryl groups having 6 to 18 carbon atoms. Ar 1 The substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl groups are used. Ar 2 for hydrogen atom, or Substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, L 1 For substituted or unsubstituted aryl groups with 6 to 18 carbon atoms in the cyclic group, p is 0 or 1, (L) 1 0 refers to a single bond. The R 1 When the expression "substituted or unsubstituted" is used, the substituent is selected from the group consisting of unsubstituted alkyl groups having 1 to 18 carbon atoms, unsubstituted cycloalkyl groups having 3 to 6 carbon atoms, and unsubstituted aryl groups having 6 to 18 carbon atoms. The Ar 1 and Ar 2 When the expression is "substituted or unsubstituted", the substituent is selected from the group consisting of unsubstituted alkyl groups with 1 to 6 carbon atoms, unsubstituted cycloalkyl groups with 3 to 6 carbon atoms, unsubstituted aryl groups with 6 to 18 carbon atoms, and unsubstituted heterocyclic groups with 5 to 18 carbon atoms. The L 1 When the expression is "substituted or unsubstituted", the substituent is selected from the group consisting of unsubstituted alkyl groups having 1 to 18 carbon atoms, unsubstituted cycloalkyl groups having 3 to 6 carbon atoms, and unsubstituted aryl groups having 6 to 18 carbon atoms.

2. The compound according to claim 1, which is represented by the following formula (4), In equation (4), R 10 ~R 14 Each independently hydrogen atom, Unsubstituted alkyl groups having 1 to 18 carbon atoms Unsubstituted cycloalkyl groups with 3 to 6 carbon atoms, or Unsubstituted aryl groups with 6 to 18 carbon atoms, in, Selected from R 10 ~R 14 One of them is a single bond bonded to *b, selected from R 10 ~R 14 The other one is a single bond that bonds with *c. Y 1 X 1 ~X 8 、*a、HAr 2 Ar 1 Ar 2 L 1 p is defined in the same way as in equation (1).

3. The compound according to claim 2, which is represented by the following formula (4A) or (4B), In equations (4A) and (4B), R 20 ~R 24 and R 30 ~R 37 Each independently hydrogen atom, Unsubstituted alkyl groups having 1 to 18 carbon atoms Unsubstituted cycloalkyl groups with 3 to 6 carbon atoms, or Unsubstituted aryl groups with 6 to 18 carbon atoms, in, Selected from R 30 ~R 37 One of them is a single bond that bonds with the *d bond. Y 1 X 1 ~X 8 、*a、Ar 1 Ar 2 L 1 p is defined the same as in equation (1), and *b, *c, and R 10 ~R 14 Same as the definition in equation (4).

4. The compound according to claim 2, wherein, R 10 ~R 14 Each independently hydrogen atom, Unsubstituted alkyl groups having 1 to 6 carbon atoms Unsubstituted cycloalkyl groups with 3 to 6 carbon atoms, or Unsubstituted aryl groups with 6 to 18 carbon atoms in a cyclic ring.

5. The compound according to claim 3, wherein, R 20 ~R 24 Each independently hydrogen atom, Unsubstituted alkyl groups having 1 to 6 carbon atoms Unsubstituted cycloalkyl groups with 3 to 6 carbon atoms, or Unsubstituted aryl groups with 6 to 18 carbon atoms in a cyclic ring.

6. The compound according to claim 3, wherein, R 30 ~R 37 Each independently hydrogen atom, Unsubstituted alkyl groups having 1 to 6 carbon atoms Unsubstituted cycloalkyl groups with 3 to 6 carbon atoms, or Unsubstituted aryl groups with 6 to 18 carbon atoms in a cyclic ring.

7. The compound according to claim 2, which is represented by the following formula (5), In equation (5), Y 1 X 1 ~X 8 、*a、HAr 2 Ar 1 Ar 2 L 1 And p is defined the same as in equation (1), R 10 R 12 and R 14 Same as the definition in equation (4).

8. The compound according to claim 3, which is represented by the following formula (4A), In equation (4A), Y 1 X 1 ~X 8 、*a、Ar 1 Ar 2 L 1 p is defined the same as in equation (1), and *b, *c, and R 10 ~R 14 Same as the definition in equation (4), R 20 ~R 24 Same as the definition in equation (4A).

9. The compound according to claim 3, which is represented by the following formula (4A-1), In equation (4A-1), Y 1 X 1 ~X 8 、*a、Ar 1 Ar 2 L 1 And p is defined the same as in equation (1), R 10 R 12 and R 14 Same as the definition in equation (4), R 20 ~R 24 Same as the definition in equation (4A).

10. The compound according to claim 3, which is represented by the following formula (4A-1a), In equation (4A-1a), Y 1 Ar 1 Ar 2 L 1 And p is defined the same as in equation (1), R 10 R 12 and R 14 Same as the definition in equation (4), R 20 ~R 24 Same as the definition in equation (4A).

11. The compound according to claim 3, which is represented by the following formula (4A-1a-1) or (4A-1a-2), In formula (4A-1a-1) or (4A-1a-2), Y 1 Ar 1 Ar 2 L 1 And p is defined the same as in equation (1), R 10 R 12 and R 14 Same as the definition in equation (4), R 20 ~R 24 Same as the definition in equation (4A).

12. The compound according to claim 3, which is represented by the following formula (4B-1), In equation (4B-1), Y 1 X 1 ~X 8 、*a、Ar 1 Ar 2 L 1 And p is defined the same as in equation (1), R 10 R 12 and R 14 Same as the definition in equation (4), *d and R 30 ~R 37 Same as the definition in equation (4B).

13. The compound according to claim 3, which is represented by the following formula (4B-1b), In equation (4B-1b), Y 1 Ar 1 Ar 2 L 1 And p is defined the same as in equation (1), R 10 R 12 and R 14 Same as the definition in equation (4), *d and R 30 ~R 37 Same as the definition in equation (4B).

14. The compound according to claim 3, which is represented by the following formula (4B-1b-1) or (4B-1b-2), In formula (4B-1b-1) or (4B-1b-2), Y 1 Ar 1 Ar 2 L 1 And p is defined the same as in equation (1), R 10 R 12 and R 14 Same as the definition in equation (4), *d and R 30 ~R 37 Same as the definition in equation (4B).

15. The compound according to claim 3, which is represented by the following formula (4B'-1) or (4B'-2), In formula (4B'-1) or (4B'-2), Y 1 X 1 ~X 8 、*a、Ar 1 Ar 2 L 1 And p is defined the same as in equation (1), R 10 ~R 14 Same as the definition in equation (4), *b, *c and R 30 ~R 37 Same as the definition in equation (4B).

16. The compound according to any one of claims 1 to 15, wherein, Ar 1 It is an unsubstituted phenyl, unsubstituted biphenyl, or unsubstituted naphthyl group.

17. The compound according to any one of claims 1 to 15, wherein, Ar 1 The phenyl group can be substituted or unsubstituted.

18. The compound according to any one of claims 1 to 15, wherein, Ar 2 It is an unsubstituted aryl group with 6 to 18 carbon atoms in a cyclic ring.

19. The compound according to any one of claims 1 to 15, wherein, Ar 2 The substituted or unsubstituted aryl group with 6 to 18 carbon atoms is selected from phenyl, biphenyl, naphthyl, and fluorene.

20. The compound according to any one of claims 1 to 15, wherein, Ar 2 It can be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted fluorene group.

21. The compound according to any one of claims 1 to 15, wherein, Ar 2 The fluorene group can be substituted or unsubstituted.

22. The compound according to any one of claims 1 to 15, wherein, L 1 It is an unsubstituted aryl group with 6 to 18 cyclic carbons.

23. The compound according to any one of claims 1 to 15, wherein, L 1 The substituted or unsubstituted arylene group with 6 to 18 carbon atoms is selected from phenylene, biphenylene, and naphthylene.

24. The compound according to any one of claims 1 to 15, wherein, L 1 It can be a substituted or unsubstituted phenylene.

25. The compound according to any one of claims 1 to 15, wherein, Y 1 It is an oxygen atom.

26. The compound according to any one of claims 1 to 15, wherein, Y 1 It is a sulfur atom.

27. The compound according to claim 1, wherein, When expressed as "substituted or unsubstituted", the substituents are all unsubstituted groups.

28. The compound according to any one of claims 2 to 15, wherein, R is not a single bond 10 ~R 14 All are hydrogen atoms.

29. The compound according to any one of claims 3, 5, 6 and 8-11, wherein, R 20 ~R 24 All are hydrogen atoms.

30. The compound according to any one of claims 3, 5, 6 and 12-15, wherein, R is not a single bond 30 ~R 37 All are hydrogen atoms.

31. The compound according to any one of claims 1 to 15, wherein, p is 0.

32. The compound according to claim 1, wherein it is any one of the following compounds: 。 33. The compound according to any one of claims 1 to 15, wherein, The compound represented by formula (1) contains at least one deuterium atom.

34. A material for an organic electroluminescent element, comprising any one of claims 1 to 33.

35. An organic electroluminescent element having a cathode, an anode, and an organic layer located between the cathode and the anode, the organic layer comprising a light-emitting layer, at least one layer of the organic layer comprising a compound according to any one of claims 1 to 33.

36. The organic electroluminescent element according to claim 35, wherein, The organic layer includes an electron transport region located between the cathode and the light-emitting layer, and the electron transport region contains the compound.

37. The organic electroluminescent element according to claim 36, wherein, The electron transport region includes a first electron transport layer on the anode side and a second electron transport layer on the cathode side, wherein the first electron transport layer contains the compound, the second electron transport layer contains the compound, or both the first electron transport layer and the second electron transport layer contain the compound.

38. The organic electroluminescent element according to claim 36, wherein, The electron transport region also includes a hole-blocking layer on the cathode side, which contains the compound.

39. The organic electroluminescent element according to claim 38, wherein, The hole blocking layer is adjacent to the light-emitting layer.

40. The organic electroluminescent element according to any one of claims 35 to 39, wherein, The light-emitting layer contains fluorescent dopant material.

41. The organic electroluminescent element according to any one of claims 35 to 39, wherein, The light-emitting layer contains phosphorescent dopant material.

42. An electronic device comprising an organic electroluminescent element according to any one of claims 35 to 41.

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