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

Abstract

A compound represented by formula (A) or a compound represented by formula (B) and containing at least one deuterium atom. An organic electroluminescent element comprising the compound; and an electronic device comprising such an organic electroluminescent element. Each symbol in each formula is as defined in the specification.

Description

Technical Field

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

[0002] Generally speaking, an organic electroluminescent element (hereinafter sometimes referred to as an "organic EL element") consists of an anode, a cathode, and an organic layer sandwiched between the anode and the cathode. When a voltage is applied between the two electrodes, electrons are injected from the cathode side into the luminescent region, and holes are injected from the anode side into the luminescent region. The injected electrons and holes recombine in the luminescent region to form an excited state, which emits light when the excited state returns to the ground state. Therefore, the development of materials that can efficiently transport electrons or holes to the luminescent region and facilitate recombination of electrons and holes is important in obtaining high-performance organic EL elements.

[0003] Patent Documents 1 to 9 disclose compounds useful as materials for organic electroluminescent devices.

[0004] Prior art literature

[0005] Patent Literature

[0006] Patent Document 1: U.S. Patent Application Publication No. 2019 / 0136127

[0007] Patent Document 2: International Publication No. 2022 / 065745

[0008] Patent Document 3: International Publication No. 2022 / 009999

[0009] Patent Document 4: International Publication No. 2016 / 190600

[0010] Patent Document 5: International Publication No. 2017 / 043757

[0011] Patent Document 6: International Publication No. 2019 / 185061

[0012] Patent Document 7: International Publication No. 2020 / 231197

[0013] Patent Document 8: U.S. Patent Application Publication No. 2020 / 0203620

[0014] Patent Document 9: International Publication No. 2009 / 145016 Summary of the Invention

[0015] Problems to be solved by the invention

[0016] Conventionally, a large number of compounds for organic EL devices have been reported, but compounds that further improve the performance of organic EL devices are still being sought.

[0017] The present invention has been made to solve the above-mentioned problems, and an object of the present invention is to provide a compound that further improves the performance of an organic EL element, an organic EL element with further improved element performance, and an electronic device including such an organic EL element.

[0018] Means used to solve problems

[0019] The present inventors have conducted intensive studies on the performance of organic EL devices containing the compounds described in the above-mentioned patent documents and other compounds. As a result, they have discovered that monoamines represented by the following formula (A) and monoamines represented by the following formula (B) and containing at least one deuterium atom provide organic EL devices with further improved device performance.

[0020] In one embodiment, the present invention provides a compound represented by the following formula (A).

[0021] [Chemical Formula 1]

[0022]

[0023] (In formula (A),

[0024] N * The central nitrogen atom.

[0025] k is 0 or 1.

[0026] When k is 0, select R a1 ~R a6 One of them is a single bond bonded to *x.

[0027] When k is 1, R a1 With R a2 、R a2 With R a3 、R a3 With R a4 、R a5 With R a6 、R a7 With R a8 or R a9 With R a10 One of them is a single bond bonded to *a, and the other is a single bond bonded to *b,

[0028] In the selection of R a1 With R a2 、R a2 With R a3 、R a3 With R a4 , and Ra5 one of the pair of R a6 one of the pair of R a1 one of the pair of R a6 one of the pair of R a11 one of the pair of R a14 one of the pair of R

[0029] one of the pair of R a7 one of the pair of R a8 one of the pair of R a9 one of the pair of R a10 one of the pair of R a1 one of the pair of R a6 one of the pair of R

[0030] one of the pair of R a1 one of the pair of R a10 one of the pair of R a11 one of the pair of R a14 each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having a carbon number of 1 to 50, a substituted or unsubstituted cyclic alkyl group having a ring-forming carbon number of 3 to 50, or a halogen atom.

[0031] two adjacent ones of the pair of R a11 two adjacent ones of the pair of R a14 are not bonded to each other and thus do not form a ring.

[0032] one of the pair of R a21 one of the pair of R a24 is a hydrogen atom.

[0033] X a1 is an oxygen atom or a sulfur atom.

[0034] one of the pair of L a1 one of the pair of L a4 each independently is a single bond or is represented by the following formulae (i) to (iii).

[0035] [Chemical Formula 2]

[0036]

[0037] one of the pair of R 1 one of the pair of R 5 is a single bond,

[0038] one of the pair of R 11 one of the pair of R 15 is a single bond, and16 ~R 20 The other one in is a single bond bonded to *6,

[0039] Selected from R 21 ~R 28 One of them is a single bond bonded to *9, selected from R 21 ~R 28 The other one is a single bond bonded to *10.

[0040] R other than the single bond 1 ~R 5 , R other than the single bond 11 ~R 20 , and R other than the single bond 21 ~R 28 Each of them is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 )、-O-(R 904 )、-S-(R 905 ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0041] R 901 ~R 905 each independently represents 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 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0042] In R 901 If there are two or more, two or more R 901 Same or different from each other,

[0043] In R 902 If there are two or more, two or more R 902 Same or different from each other,

[0044] In R 903 If there are two or more, two or more R 903 Same or different from each other,

[0045] In R 904 If there are two or more, two or more R 904 Same or different from each other,

[0046] In R905 If there are two or more, two or more R 905 Same as or different from each other.

[0047] *1, *4, and *8 represent the bonding position to the central nitrogen atom N*, or *x,

[0048] *3, *7, and *11 indicate the same as Ar a1 、Ar a2 Or the bonding position of benzene ring A.

[0049] R selected from other than said single bond 1 ~R 5 , R other than the single bond 11 ~R 20 , and R other than the single bond 21 ~R2 8 Two adjacent groups in the group may be bonded to each other to form a substituted or unsubstituted ring structure, or may not be bonded to each other to form no ring.

[0050] Ar a1 and Ar a2 Each is independently represented by the following formula (a) to (f).

[0051] [Chemical Formula 3]

[0052]

[0053] (In formula (a),

[0054] *21 is with L a1 or L a2 bonding position.

[0055] Selected from R 101 ~R 105 One of them is a single bond to *22, selected from R 106 ~R 110 One of them is a single bond to *23.

[0056] R other than the single bond 101 ~R 105 , and R 106 ~R 110 Each independently represents a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms.

[0057] R selected from other than said single bond 101 ~R 105 The two adjacent ones in the molecule are not bonded to each other and do not form a ring.

[0058] R selected from other than said single bond 106~R 110 The two adjacent ones in the molecule are not bonded to each other and do not form a ring.

[0059] R 111 ~R 115 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.

[0060] Selected from R 111 ~R 115 The two adjacent ones in the molecule are not bonded to each other and do not form a ring.

[0061] m is 0, 1 or 2, and n is 0 or 1.

[0062] When m=0 and n=0, *23 represents *21.

[0063] When m=0 and n=1, *22 represents *21.

[0064] When m=1 and n=0, *23 represents *22.

[0065] Among them, when k is 0, R a5 is a single bond bonded to *x, L a1 , L a3 and L a4 When Ar is a single bond, a1 In the formula (a) represented by: m+n is 0, 1 or 3,

[0066] When k is 0, R a5 is a single bond bonded to *x, L a3 and L a4 For a single bond, L a1 In the case represented by formula (i), Ar a1 In the formula (a), m+n is 0, 2 or 3,

[0067] When k is 0, R a5 is a single bond bonded to *x, L a3 and L a4 For a single bond, L a1 In the case represented by formula (i), Ar a1 In the formula (a), m+n is 1, 2 or 3.

[0068] [Chemical Formula 4]

[0069]

[0070] (In formula (b),

[0071] *24 is with La1 or L a2 is a bonding position of the single bond.

[0072] is selected from R 121 to R 128 one of which is a single bond to *25.

[0073] R 121 to R 128 each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having a carbon number of 1 to 10, or a substituted or unsubstituted aromatic ring-forming aryl group having a carbon number of 6 to 12.

[0074] adjacent 2 of R 121 to R 128 other than the single bond do not bond to each other to form a ring.

[0075] [Chemical Formula 5]

[0076]

[0077] (in formula (c),

[0078] *26 is a bonding position of the single bond of L a1 or L a2 .

[0079] is selected from R 131 to R 140 one of which is a single bond to *27.

[0080] R 131 to R 140 each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having a carbon number of 1 to 10, or a substituted or unsubstituted aromatic ring-forming aryl group having a carbon number of 6 to 12.

[0081] adjacent 2 of R 131 to R 140 other than the single bond do not bond to each other to form a ring.

[0082] wherein, in the case where R a5 is a single bond to *x, L a1 to L a4 is a single bond, 1 of R 131 , R 132 , R 134 , R 135 , and R 137 to R 140 is a single bond to *27.

[0083] [Chemical Formula 6]

[0084]

[0085] (In formula (d),

[0086] *28 is with L a1 or L a2 bonding position.

[0087] X 11 For oxygen atoms, sulfur atoms, CR A R B or NR C .

[0088] R A and RB are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and R A and RB may be bonded to each other to form a substituted or unsubstituted ring structure, or may not be bonded to each other to form no ring.

[0089] R C It is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0090] l is 0 or 1.

[0091] When l is 0, select R A 、R B 、R C and R 141 ~R 148 One of them is a single bond to *29, or

[0092] R A or RB may represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, R A or RB may be bonded to each other to form a substituted or unsubstituted ring structure or R C The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms which may be represented is bonded to *29 via a single bond.

[0093] When l is 1, R 141 With R 142 、R 142 With R 143 , or R 143 With R 144 One of them is a single bond bonded to *c, and the other is a single bond bonded to *d,

[0094] R selected from single bonds other than those bonded to *c and *d 141 ~R 144 、R145 ~R 148 、R A 、R B 、R C , and R 200 ~R 203 One of them is a single bond to *29, or

[0095] R A or RB may represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or R A or RB may be bonded to each other to form a substituted or unsubstituted ring structure, or R C The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms which may be represented is bonded to *29 via a single bond.

[0096] R other than the single bond 141 ~R 148 , and R other than the single bond 200 ~R 203 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.

[0097] R selected from other than said single bond 141 ~R 148 , and R other than the single bond 200 ~R 203 The two adjacent ones in the molecule are not bonded to each other and do not form a ring.)

[0098] [Chemical Formula 7]

[0099]

[0100] (In formula (e),

[0101] *30 is with L a1 or L a2 bonding position.

[0102] Selected from R 151 ~R 155 One of them is a single bond to *31, selected from R 151 ~R 155 The other one is a single bond to *32.

[0103] R other than the single bond 151 ~R 155 Each independently represents a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group.

[0104] R selected from other than said single bond 151~R 155 The two adjacent ones in the molecule are not bonded to each other and do not form a ring.

[0105] R 161 ~R 165 and R 171 ~R 175 Each independently represents a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms.

[0106] Selected from R 161 ~R 165 At least one pair of adjacent two of the substituted benzene groups may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form a ring.

[0107] Selected from R 171 ~R 175 At least one pair of adjacent two of the phenyl groups may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form no ring.

[0108] [Chemical Formula 8]

[0109]

[0110] (In formula (f),

[0111] *32 is the same as L a1 or L a2 bonding position.

[0112] Selected from R 181 ~R 192 One of them is a single bond to *33.

[0113] R other than the single bond 181 ~R 192 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.

[0114] R selected from other than said single bond 181 ~R 192 The two adjacent ones in the molecule are not bonded to each other and do not form a ring.

[0115] Among them, in L a1 and L a2 Phenylene, L a3 and L a4 is a single bond, Ar a1 and Ar a2 In the case of the above formula (b), L a1 is 1,2-phenylene or 1,4-phenylene.)

[0116] In one aspect, the present application provides a compound represented by the following formula (B) and containing at least one deuterium atom.

[0117] [Chemical Formula 9]

[0118]

[0119] (In formula (B),

[0120] N* is a central nitrogen atom.

[0121] p is 0 or 1.

[0122] In the case where p is 0, R b4 or R b6 is a single bond to *y.

[0123] In the case where p is 1, R b1 and R b2 , R b2 and R b3 , R b3 and R b4 , R b5 and R b6 , R b7 and R b8 , R b8 and R b9 , or R b9 and R b10 are one of a single bond to *e and the other is a single bond to *f,

[0124] In the case where one of R b3 and R b4 is a single bond to *e and the other is a single bond to *f, R b6 is a single bond to *y,

[0125] In the case where one of R b5 and R b6 is a single bond to *e and the other is a single bond to *f, R b4 is a single bond to *y,

[0126] In the case where one of R b3 and R b4 is not a single bond to *e and the other is not a single bond to *f and one of R b5 and R b6 is not a single bond to *e and the other is not a single bond to *f, R b4 or R b6 is a single bond to *y.

[0127] R is not a single bond to *y and is not a single bond to *e and *f b1 ~R b10 , and R that is not a single bond to *y b11 ~R b14 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a halogen atom.

[0128] R selected from a single bond other than a bond to *y b11 ~R b14 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring.

[0129] R b21 ~R b24 A hydrogen atom.

[0130] X b1 is an oxygen atom or a sulfur atom.

[0131] L b1 ~L b4 Each independently represents a single bond or is represented by the following formulae (i) to (iii).

[0132] [Chemical Formula 10]

[0133]

[0134] Selected from R 1 ~R 5 One of them is a single bond to *2,

[0135] Selected from R 11 ~R 15 One of them is a single bond to *5, selected from R 16 ~R 20 The other one in is a single bond bonded to *6,

[0136] Selected from R 21 ~R 28 One of them is a single bond bonded to *9, selected from R 21 ~R 28 The other one is a single bond bonded to *10.

[0137] R other than the single bond 1 ~R 5 , R other than the single bond 11 ~R 20 , and R other than the single bond 21 ~R 28Each of them is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 )、-O-(R 904 )、-S-(R 905 ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0138] R 901 ~R 905 each independently represents 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 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0139] In R 901 If there are two or more, two or more R 901 Same or different from each other,

[0140] In R 902 If there are two or more, two or more R 902 Same or different from each other,

[0141] In R 903 If there are two or more, two or more R 903 Same or different from each other,

[0142] In R 904 If there are two or more, two or more R 904 Same or different from each other,

[0143] In R 905 If there are two or more, two or more R 905 Same as or different from each other.

[0144] *1, *4, and *8 represent the central nitrogen atom N * The bonding position, or *y,

[0145] *3, *7, and *11 indicate the same as Ar b1 、Ar b2 Or the bonding position of benzene ring B.

[0146] R selected from other than said single bond 1 ~R 5 , R other than the single bond 11 ~R 20, and R 21 ~R 28 Two adjacent ones among R b1 and Ar b2 may be bonded to each other to form a substituted or unsubstituted ring structure, or may not be bonded to each other and thus not form a ring.

[0147] Ar b1 and Ar b2 are each independently represented by the following formulae (a) to (f).

[0148] [Chemical Formula 11]

[0149]

[0150] (In formula (a),

[0151] *21 is a bonding position to L 101 or L 105 .

[0152] One selected from R 106 ~R 110 is a single bond to *22, and one selected from R 101 ~R 105 is a single bond to *23.

[0153] R 106 ~R 110 , and R 101 ~R 105 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbons, or an unsubstituted aryl group having 6 to 12 ring-forming carbons.

[0154] Two adjacent ones selected from R 106 ~R 110 are not bonded to each other and thus not form a ring.

[0155] Two adjacent ones selected from R 106 ~R 110 are not bonded to each other and thus not form a ring.

[0156] R 111 ~R 115 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbons, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbons, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms.

[0157] Two adjacent ones selected from R 111 ~R 115 are not bonded to each other and thus not form a ring.

[0158] m is 0, 1, or 2, and n is 0 or 1. The case where m is 2 and n is 0 is excluded.

[0159] In the case where m = 0 and n = 0, *23 represents *21.

[0160] In the case where m = 0 and n = 1, *22 represents *21.

[0161] In the case where m = 1 and n = 0, *23 represents *22.

[0162] [Chemical Formula 12]

[0163]

[0164] (In formula (b),

[0165] *24 is a bonding position to L b1 or L b2 .

[0166] one selected from R 121 to R 128 is a single bond to *25.

[0167] R 121 to R 128 other than the single bond are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having a carbon number of 1 to 10, or a substituted or unsubstituted aromatic ring-forming aryl group having a carbon number of 6 to 12.

[0168] adjacent 2 selected from R 121 to R 128 other than the single bond are not bonded to each other without forming a ring.

[0169] [Chemical Formula 13]

[0170]

[0171] (In formula (c),

[0172] *26 is a bonding position to L b1 or L b2 .

[0173] one selected from R 131 to R 140 is a single bond to *27.

[0174] R 131 to R 140 other than the single bond are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having a carbon number of 1 to 10, or a substituted or unsubstituted aromatic ring-forming aryl group having a carbon number of 6 to 12.

[0175] adjacent 2 selected from R 131 to R 140 other than the single bond are not bonded to each other without forming a ring.two adjacent ones of R1to R4in the formula (a) are not bonded to each other without forming a ring.

[0176] [Chemical Formula 14]

[0177]

[0178] (in the formula (d), R1to R4are not bonded to each other without forming a ring.

[0179] *28 is a bonding position to Lb1or Lb 2 .

[0180] X 11 is an oxygen atom, a sulfur atom, CR A R B , or NR C .

[0181] R A and RBare each independently a hydrogen atom, a substituted or unsubstituted alkyl group having a carbon number of 1 to 30, a substituted or unsubstituted ring-forming cycloalkyl group having a carbon number of 3 to 50, or a substituted or unsubstituted ring-forming aryl group having a carbon number of 6 to 30, R A and RBmay be bonded to each other to form a substituted or unsubstituted ring structure, or may not be bonded to each other without forming a ring.

[0182] R C is a hydrogen atom, a substituted or unsubstituted alkyl group having a carbon number of 1 to 30, a substituted or unsubstituted ring-forming aryl group having a carbon number of 6 to 30, or a substituted or unsubstituted ring-forming heterocyclic group having an atom number of 5 to 30.

[0183] l is 0 or 1.

[0184] when l is 0, one selected from R A , R B , R C , and R 141 to R 148 is a single bond to *29, or

[0185] R A or R B may represent a substituted or unsubstituted ring-forming aryl group having a carbon number of 6 to 30, R A or R B may represent a substituted or unsubstituted ring structure formed by the bonding of R C to R 141 may represent a substituted or unsubstituted ring-forming aryl group having a carbon number of 6 to 30, bonded to *29 via a single bond.

[0186] when l is 1, R 142 and R 142 , R 143 and R 143 , or R 144 and ROne of them is a single bond bonded to *c, and the other is a single bond bonded to *d,

[0187] R selected from single bonds other than those bonded to *c and *d 141 ~R 144 、R 145 ~R 148 、R A 、R B 、R C , and R 200 ~R 203 One of them is a single bond to *29, or

[0188] R A or RB may represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or R A or RB may be bonded to each other to form a substituted or unsubstituted ring structure, or R C The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms which may be represented is bonded to *29 via a single bond.

[0189] Among them, in L b1 , L b3 and L b4 is a single bond, l is 0, X 11 CR A R B In the case of R 141 ~R 148 One of them is a single bond to *29.

[0190] R other than the single bond 141 ~R 148 , and R other than the single bond 200 ~R 203 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.

[0191] R is selected from other than said single bond 141 ~R 148 , and R other than the single bond 200 ~R 203 The two adjacent ones in the molecule are not bonded to each other and do not form a ring.)

[0192] [Chemical Formula 15]

[0193]

[0194] (In formula (e),

[0195] *30 is the same as Lb1 or Lb 2bonding position.

[0196] Selected from R 151 ~R 155 One of them is a single bond to *31, selected from R 151 ~R 155 The other one is a single bond to *32.

[0197] R other than the single bond 151 ~R 155 Each independently represents a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group.

[0198] R is selected from other than said single bond 151 ~R 155 The two adjacent ones in the molecule are not bonded to each other and do not form a ring.

[0199] R 161 ~R 165 and R 171 ~R 175 Each independently represents a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms.

[0200] Selected from R 161 ~R 165 At least one pair of adjacent two of the substituted benzene groups may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form a ring.

[0201] Selected from R 171 ~R 175 At least one pair of adjacent two of the phenyl groups may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form no ring.

[0202] [Chemical Formula 16]

[0203]

[0204] (In formula (f),

[0205] *32 is the same as L b1 or L b2 bonding position.

[0206] Selected from R 181 ~R 192 One of them is a single bond to *33.

[0207] R other than the single bond 181 ~R 192 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.

[0208] R is selected from other than said single bond 181 ~R 192 The two adjacent ones in the molecule are not bonded to each other and do not form a ring.

[0209] Among them, in L b1 ~L b4 When Ar is a single bond, b1 Represented by formula (a) or (c) to (f), in Ar b1 In the case of formula (a), m+n is 1, 2 or 3.)

[0210] In another embodiment, the present invention provides a material for an organic EL device comprising a compound represented by the above formula (A) or a compound represented by the above formula (B) and containing at least one deuterium atom.

[0211] In another embodiment, the present invention provides an organic electroluminescent element, comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a light-emitting layer, and at least one layer of the organic layer comprises a compound represented by the above formula (A) or a compound represented by the above formula (B) and containing at least one deuterium atom.

[0212] In another embodiment, the present invention provides an organic electroluminescent device comprising an anode, a light-emitting layer, and a cathode, an organic layer between the anode and the light-emitting layer, and at least one of the organic layers comprising a compound represented by formula (B').

[0213] In another embodiment, the present invention provides an electronic device comprising the organic electroluminescent element.

[0214] Effects of the Invention

[0215] An organic EL device containing the compound represented by the above formula (A) or the compound represented by the above formula (B) and containing at least one deuterium atom exhibits improved device performance.

[0216] In addition, an organic EL device containing the compound represented by formula (B') exhibits improved device performance. BRIEF DESCRIPTION OF THE DRAWINGS

[0217] Figure 1 This is a schematic diagram showing an example of the layer structure of an organic EL element according to one embodiment of the present invention.

[0218] Figure 2 This is a schematic diagram showing another example of the layer structure of the organic EL element according to one embodiment of the present invention.

[0219] Figure 3is a schematic view showing another example of a layer configuration of an organic EL element according to an embodiment of the present application. DETAILED DESCRIPTION

[0220] [Definitions]

[0221] In the present specification, a hydrogen atom means to include isotopes different in the number of neutrons, i.e., protium, deuterium, and tritium.

[0222] In the present specification, in a chemical structural formula, the bondable positions of symbols such as "R" and "D" indicating a deuterium atom are set to be bonded to a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom, without being explicitly shown.

[0223] In the present specification, the ring-forming carbon number refers to the number of carbon atoms among atoms constituting a ring itself in a compound in which atoms are bonded in a ring shape (e.g., a monocyclic compound, a fused ring compound, a bridged ring compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon included in the substituent is not included in the ring-forming carbon number. The "ring-forming carbon number" described below is similarly set unless otherwise noted. For example, the ring-forming carbon number of a benzene ring is 6, the ring-forming carbon number of a naphthalene ring is 10, the ring-forming carbon number of a pyridine ring is 5, and the ring-forming carbon number of a furan ring is 4. In addition, for example, the ring-forming carbon number of a 9,9-diphenylfluorene group is 13, and the ring-forming carbon number of a 9,9'-spirobifluorene group is 25.

[0224] In addition, when an alkyl group is substituted as a substituent on a benzene ring, for example, the number of carbons of the alkyl group is not included in the ring-forming carbon number of the benzene ring. Thus, the ring-forming carbon number of a benzene ring substituted with an alkyl group is 6. In addition, when an alkyl group is substituted as a substituent on a naphthalene ring, for example, the number of carbons of the alkyl group is not included in the ring-forming carbon number of the naphthalene ring. Thus, the ring-forming carbon number of a naphthalene ring substituted with an alkyl group is 10.

[0225] In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (such as a monocyclic compound, a condensed ring compound, a bridged ring compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are cyclically bonded. Atoms that do not constitute a ring (such as a hydrogen atom that terminates the bond of the atoms constituting the ring) and atoms contained in a substituent when the ring is substituted by a substituent are not included in the number of ring atoms. The "number of ring atoms" recorded below is set in the same manner as long as it is not otherwise stated. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or the number of atoms constituting a substituent are not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring bonded with a hydrogen atom or a substituent is 6. For example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinazoline ring. Therefore, the number of ring atoms of the quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

[0226] In this specification, "carbon number XX to YY" in the expression "a substituted or unsubstituted ZZ group having XX to YY carbon atoms" refers to the carbon number of the ZZ group when it is unsubstituted and does not include the carbon number of the substituent when it is substituted. Here, "YY" is greater than "XX," "XX" is an integer greater than 1, and "YY" is an integer greater than 2.

[0227] In this specification, "atomic number XX to YY" in the expression "a substituted or unsubstituted ZZ group having an atomic number of XX to YY" indicates the atomic number of the ZZ group when it is unsubstituted and does not include the atomic number of the substituent when it is substituted. Here, "YY" is greater than "XX," "XX" is an integer greater than 1, and "YY" is an integer greater than 2.

[0228] In this specification, an unsubstituted ZZ group means a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group means a case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group".

[0229] In this specification, "unsubstituted" in the context of a "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group is not replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.

[0230] In this specification, "substituted" in the context of a "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced with a substituent. Similarly, "substituted" in the context of a "BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are replaced with an AA group.

[0231] "Substituents described in this specification"

[0232] The substituents described in this specification are described below.

[0233] The number of ring carbon atoms in the "unsubstituted aryl group" described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification.

[0234] The number of ring atoms in the "unsubstituted heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in the present specification.

[0235] The number of carbon atoms in the "unsubstituted alkyl group" described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in the present specification.

[0236] The number of carbon atoms in the "unsubstituted alkenyl group" described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified in the present specification.

[0237] The number of carbon atoms in the "unsubstituted alkynyl group" described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified in the present specification.

[0238] The number of ring carbon atoms in the "unsubstituted cycloalkyl group" described in the present specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified in the present specification.

[0239] The number of ring carbon atoms in the "unsubstituted arylene group" described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification.

[0240] The number of ring atoms in the "unsubstituted divalent heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in the present specification.

[0241] The number of carbon atoms in the "unsubstituted alkylene group" described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in the present specification.

[0242] "Substituted or unsubstituted aryl"

[0243] Specific examples of the "substituted or unsubstituted aryl group" described in this specification (Specific Example Group G1) include the following unsubstituted aryl groups (Specific Example Group G1A) and substituted aryl groups (Specific Example Group G1B). (Herein, an unsubstituted aryl group refers to a case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and a substituted aryl group refers to a case where the "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, the term "aryl group" alone includes both "unsubstituted aryl groups" and "substituted aryl groups."

[0244] A "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with a substituent. Examples of the "substituted aryl group" include groups in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with a substituent, as described in the following specific example group G1A, and examples of substituted aryl groups described in the following specific example group G1B. It should be noted that the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed here are merely examples, and the "substituted aryl groups" described in this specification also include groups in which a hydrogen atom bonded to a carbon atom of an aryl group in the "substituted aryl groups" in the following specific example group G1B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in a "substituted aryl group" in the following specific example group G1B is further replaced with a substituent.

[0245] Unsubstituted aryl (Specific example group G1A):

[0246] Phenyl,

[0247] p-Biphenyl,

[0248] m-Biphenyl,

[0249] o-biphenyl,

[0250] 4-terphenyl-4-yl,

[0251] 4-terphenyl-3-yl,

[0252] 4-terphenyl-2-yl,

[0253] m-terphenyl-4-yl,

[0254] m-terphenyl-3-yl,

[0255] m-terphenyl-2-yl,

[0256] o-terphenyl-4-yl,

[0257] o-terphenyl-3-yl,

[0258] o-terphenyl-2-yl,

[0259] 1-naphthyl,

[0260] 2-naphthyl,

[0261] anthryl,

[0262] benzanthryl,

[0263] phenanthryl,

[0264] benzophenanthryl,

[0265] phenalenyl,

[0266] pyrenyl,

[0267] phenalenyl,

[0268] benzo phenalenyl,

[0269] triphenylenyl,

[0270] benztriphenylenyl,

[0271] tetracenyl,

[0272] pentacenyl,

[0273] fluorenyl,

[0274] 9,9'-spirobifluorenyl,

[0275] benzofluorenyl,

[0276] dibenzo-fluorenyl,

[0277] fluorantenyl,

[0278] benzofluorantenyl,

[0279] peryl, and

[0280] a monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).

[0281] [Chemical Formula 17]

[0282]

[0283] [Chemical Formula 18]

[0284]

[0285] • Substituted aryl group (specific example group G1B): o-tolyl,

[0286] m-tolyl,

[0287] p-tolyl,

[0288] p-xylyl,

[0289] m-xylyl,

[0290] o-xylyl,

[0291] p-isopropylphenyl,

[0292] m-isopropylphenyl,

[0293] o-isopropylphenyl,

[0294] p-tert-butylphenyl,

[0295] m-tert-butylphenyl,

[0296] o-tert-butylphenyl,

[0297] 3,4,5-trimethylphenyl,

[0298] 9,9-dimethylfluorenyl,

[0299] 9,9-diphenylfluorenyl

[0300] 9,9-bis(4-methylphenyl)fluorenyl,

[0301] 9,9-bis(4-isopropylphenyl)fluorenyl,

[0302] 9,9-bis(4-tert-butylphenyl)fluorenyl,

[0303] cyanophenyl,

[0304] triphenylsilylphenyl,

[0305] trimethylsilylphenyl,

[0306] phenylnaphthyl,

[0307] naphthylphenyl, and

[0308] one or more hydrogen atoms of a monovalent group derived from the ring structure represented by General Formulae (TEMP-1) to (TEMP-15) above are replaced with a substituent.

[0309] • "substituted or unsubstituted heterocyclic group"

[0310] The "heterocyclic group" described in the present specification is a cyclic group containing at least one hetero atom in a ring-forming atom. As specific examples of the hetero atom, a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom can be given.

[0311] The "heterocyclic group" described in the present specification is a monocyclic group or a fused ring group.

[0312] The "heterocyclic group" described in the present specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0313] As specific examples of the "substituted or unsubstituted heterocyclic group" described in the present specification (specific example group G2), the following unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B) and the like can be given. (Here, the unsubstituted heterocyclic group means the case where the "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group", and the substituted heterocyclic group means the case where the "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group".) In the present specification, only the expression "heterocyclic group" includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group".

[0314] The "substituted heterocyclic group" means a group in which 1 or more hydrogen atoms of the "unsubstituted heterocyclic group" have been replaced with a substituent. Specific examples of the "substituted heterocyclic group" can be given as a group in which the hydrogen atoms of the "unsubstituted heterocyclic group" of the following specific example group G2A have been replaced, and a group in which the substituted heterocyclic groups of the following specific example group G2B have been replaced, and the like. Note that the examples of the "unsubstituted heterocyclic group" and the examples of the "substituted heterocyclic group" given here are only one example, and the "substituted heterocyclic group" described in the present specification also includes a group in which the hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself of the "substituted heterocyclic group" of the specific example group G2B have been further replaced with a substituent, and a group in which the hydrogen atoms of the substituents of the "substituted heterocyclic group" of the specific example group G2B have been further replaced with a substituent.

[0315] The specific example group G2A includes, for example, unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing 1 hydrogen atom from the ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0316] The specific example group G2B includes, for example, substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which 1 or more hydrogen atoms of the monovalent heterocyclic groups derived from the ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) have been replaced with a substituent (specific example group G2B4).

[0317] • unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1):

[0318] a pyrrolyl group,

[0319] an imidazolyl group,

[0320] a pyrazolyl group,

[0321] triazolyl,

[0322] tetrazolyl,

[0323] oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, indolizinyl, quinolizinyl, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, indazolyl, phenanthrolinyl, phenanthridinyl, acridinyl, phenoxazinyl, carbazolyl, benzocarbazolyl, morpholinyl, phenoxazinyl,

[0324] phenothiazinyl,

[0325] azacarbazolyl, and diazacarbazolyl.

[0326] • Unsubstituted heterocyclic groups containing oxygen atoms (Specific Example Group G2A2): furanyl,

[0327] oxazolyl,

[0328] isoxazolyl,

[0329] oxadiazolyl,

[0330] chromenyl,

[0331] benzofuranyl,

[0332] isobenzofuranyl,

[0333] dibenzofuranyl,

[0334] naphthobenzofuranyl,

[0335] benzoxazolyl,

[0336] benzisoxazolyl,

[0337] phenoxazinyl,

[0338] morpholinyl,

[0339] dinaphthofuranyl,

[0340] azadibenzofuranyl,

[0341] diazadibenzofuranyl,

[0342] azanaphthobenzofuranyl, and

[0343] diazanaphthobenzofuranyl.

[0344] • Unsubstituted heterocyclic groups containing sulfur atoms (Specific Example Group G2A3): thienyl,

[0345] thiazolyl,

[0346] Isothiazolyl,

[0347] Thiadiazole,

[0348] benzothienyl,

[0349] isobenzothienyl, dibenzothienyl,

[0350] naphthobenzothienyl,

[0351] Benzothiazolyl,

[0352] Benzisothiazolyl,

[0353] Phenothiazine,

[0354] dinaphthothienyl,

[0355] azadibenzothienyl,

[0356] diazadibenzothienyl,

[0357] azanaphthobenzothienyl and

[0358] diazanaphthobenzothienyl.

[0359] A monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) (Specific Example Group G2A4):

[0360] [Chemical Formula 19]

[0361]

[0362] [Chemical Formula 20]

[0363]

[0364] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each independently represents an oxygen atom, a sulfur atom, NH or CH2. A and Y A At least one of them is an oxygen atom, a sulfur atom or NH.

[0365] In the above general formulae (TEMP-16) to (TEMP-33), X A and Y A at least one of which is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the above general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0366] • Substituted heterocyclic group containing a nitrogen atom (Specific example group G2B1):

[0367] (9-phenyl)carbazolyl,

[0368] (9-biphenyl)carbazolyl,

[0369] (9-phenyl)phenylcarbazolyl,

[0370] (9-naphthyl)carbazolyl,

[0371] diphenylcarbazol-9-yl,

[0372] phenylcarbazol-9-yl,

[0373] methylbenzoimidazolyl,

[0374] ethylbenzoimidazolyl,

[0375] phenyltriazinyl,

[0376] biphenyltriazinyl,

[0377] diphenyltriazinyl,

[0378] phenylquinazolinyl, and

[0379] biphenylquinazolinyl.

[0380] • Substituted heterocyclic group containing an oxygen atom (Specific example group G2B2):

[0381] phenyldibenzofuranyl,

[0382] methyldibenzofuranyl,

[0383] tert-butyldibenzofuranyl, and

[0384] a monovalent residue of spiro[9H-courmarin-9,9'-[9H]fluorene].

[0385] • Substituted heterocyclic group containing a sulfur atom (Specific example group G2B3):

[0386] phenyldibenzothiophenyl,

[0387] methyldibenzothiophenyl,

[0388] tert-Butyldibenzothienyl, and

[0389] The monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0390] Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the above-mentioned general formulae (TEMP-16) to (TEMP-33) are replaced with substituents (Specific Example Group G2B4):

[0391] The above-mentioned "one or more hydrogen atoms of the monovalent heterocyclic group" refers to hydrogen atoms bonded to carbon atoms constituting the ring of the monovalent heterocyclic group, X A and Y A When at least one of the nitrogen atoms is NH, the hydrogen atom bonded to the nitrogen atom and X A and Y A When one of them is CH2, one or more hydrogen atoms among the hydrogen atoms of the methylene group.

[0392] "Substituted or unsubstituted alkyl"

[0393] Specific examples of "substituted or unsubstituted alkyl groups" described in this specification (Specific Example Group G3) include the following unsubstituted alkyl groups (Specific Example Group G3A) and substituted alkyl groups (Specific Example Group G3B). (Herein, unsubstituted alkyl groups refer to "substituted or unsubstituted alkyl groups" being "unsubstituted alkyl groups," and substituted alkyl groups refer to "substituted or unsubstituted alkyl groups" being "substituted alkyl groups.") Hereinafter, when simply referring to "alkyl groups," both "unsubstituted alkyl groups" and "substituted alkyl groups" are included.

[0394] "Substituted alkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl" are replaced by a substituent. Specific examples of "substituted alkyl" include the following "unsubstituted alkyl" (specific example group G3A) in which one or more hydrogen atoms are replaced by a substituent, and examples of substituted alkyl (specific example group G3B). In this specification, the alkyl group in "unsubstituted alkyl" refers to a chain alkyl group. Therefore, "unsubstituted alkyl" includes "unsubstituted alkyl" as a straight chain and "unsubstituted alkyl" as a branched chain. It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples, and the "substituted alkyl" recorded in this specification also includes a group in which the hydrogen atom of the alkyl group itself in the "substituted alkyl" of the specific example group G3B is further replaced by a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkyl" of the specific example group G3B is further replaced by a substituent.

[0395] Unsubstituted alkyl (Specific example group G3A):

[0396] methyl,

[0397] ethyl,

[0398] n-propyl,

[0399] iso-propyl,

[0400] n-butyl,

[0401] iso-butyl,

[0402] sec-butyl, and

[0403] tert-butyl.

[0404] • Substituted alkyl (Specific Example Group G3B):

[0405] heptafluoropropyl (including isomers),

[0406] pentafluoroethyl,

[0407] 2,2,2-trifluoroethyl, and

[0408] trifluoromethyl.

[0409] • "Substituted or unsubstituted alkenyl"

[0410] As specific examples of "substituted or unsubstituted alkenyl" recited in the present specification (Specific Example Group G4), the following unsubstituted alkenyl (Specific Example Group G4A) and substituted alkenyl (Specific Example Group G4B) and the like can be given. (Here, unsubstituted alkenyl means the case where "substituted or unsubstituted alkenyl" is "unsubstituted alkenyl", and substituted alkenyl means the case where "substituted or unsubstituted alkenyl" is "substituted alkenyl".) In the present specification, only when expressed as "alkenyl", both "unsubstituted alkenyl" and "substituted alkenyl" are included.

[0411] "Substituted alkenyl" means a group in which one or more hydrogen atoms in "unsubstituted alkenyl" are replaced with a substituent. As specific examples of "substituted alkenyl", examples of a group in which "unsubstituted alkenyl" (Specific Example Group G4A) has a substituent and substituted alkenyl (Specific Example Group G4B) can be given. Note that the examples of "unsubstituted alkenyl" and "substituted alkenyl" recited here are only examples, and "substituted alkenyl" recited in the present specification also includes a group in which a hydrogen atom of alkenyl itself in "substituted alkenyl" of Specific Example Group G4B is further replaced with a substituent and a group in which a hydrogen atom of a substituent in "substituted alkenyl" of Specific Example Group G4B is further replaced with a substituent.

[0412] • Unsubstituted alkenyl (Specific Example Group G4A):

[0413] Vinyl,

[0414] Allyl,

[0415] 1-butenyl,

[0416] 2-Butenyl, and

[0417] 3-Butenyl.

[0418] Substituted alkenyl (Specific example group G4B):

[0419] 1,3-butadienyl,

[0420] 1-Methylvinyl,

[0421] 1-methylallyl,

[0422] 1,1-dimethylallyl,

[0423] 2-methylallyl, and

[0424] 1,2-dimethylallyl.

[0425] "Substituted or unsubstituted alkynyl"

[0426] Specific examples of "substituted or unsubstituted alkynyl groups" described in this specification (Specific Example Group G5) include the following unsubstituted alkynyl groups (Specific Example Group G5A). (Herein, unsubstituted alkynyl groups refer to cases where "substituted or unsubstituted alkynyl groups" are "unsubstituted alkynyl groups.") When simply referring to "alkynyl groups" below, both "unsubstituted alkynyl groups" and "substituted alkynyl groups" are included.

[0427] A "substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced with a substituent. Specific examples of "substituted alkynyl groups" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl groups" (Specific Example Group G5A) are replaced with a substituent.

[0428] Unsubstituted alkynyl (Specific example group G5A):

[0429] ethynyl

[0430] "Substituted or unsubstituted cycloalkyl"

[0431] As specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group" recited in the present specification, the following unsubstituted cycloalkyl groups (specific example group G6A) and substituted cycloalkyl groups (specific example group G6B) and the like can be given. (Here, the unsubstituted cycloalkyl group means the case where the "substituted or unsubstituted cycloalkyl group" is "unsubstituted cycloalkyl group", and the substituted cycloalkyl group means the case where the "substituted or unsubstituted cycloalkyl group" is "substituted cycloalkyl group".) In the present specification, only when expressed as "cycloalkyl group", both "unsubstituted cycloalkyl group" and "substituted cycloalkyl group" are included.

[0432] The "substituted cycloalkyl group" means a group in which 1 or more hydrogen atoms in the "unsubstituted cycloalkyl group" have been replaced with a substituent group. As specific examples of the "substituted cycloalkyl group", examples of a group in which 1 or more hydrogen atoms in the "unsubstituted cycloalkyl group" (specific example group G6A) described below have been replaced with a substituent group and examples of the substituted cycloalkyl group (specific example group G6B) can be given. Note that the examples of the "unsubstituted cycloalkyl group" and the examples of the "substituted cycloalkyl group" recited here are only examples, and the "substituted cycloalkyl group" recited in the present specification also includes a group in which 1 or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl group" of specific example group G6B have been replaced with a substituent group and a group in which a hydrogen atom of the substituent group in the "substituted cycloalkyl group" of specific example group G6B has been further replaced with a substituent group.

[0433] • unsubstituted cycloalkyl groups (specific example group G6A):

[0434] cyclopropyl,

[0435] cyclobutyl,

[0436] cyclopentyl,

[0437] cyclohexyl,

[0438] 1-adamantyl,

[0439] 2-adamantyl,

[0440] 1-norbornyl, and

[0441] 2-norbornyl.

[0442] • substituted cycloalkyl groups (specific example group G6B):

[0443] 4-methylcyclohexyl.

[0444] • a group represented by "-Si(R 901 )(R 902 )(R 903 )"

[0445] as the group represented by -Si(R 901 )(R 902 )(R 903 ) described in the present specification, specific examples (specific example group G7) can be mentioned

[0446] -Si(G1)(G1)(G1),

[0447] -Si(G1)(G2)(G2),

[0448] -Si(G1)(G1)(G2),

[0449] -Si(G2)(G2)(G2),

[0450] -Si(G3)(G3)(G3), and

[0451] -Si(G6)(G6)(G6). Here,

[0452] G1is "substituted or unsubstituted aryl group" described in the specific example group G1.

[0453] G2is "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0454] G3is "substituted or unsubstituted alkyl group" described in the specific example group G3.

[0455] G6is "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.

[0456] The plurality of G1in -Si(G1)(G1)(G1) are the same as or different from each other.

[0457] The plurality of G2in -Si(G1)(G2)(G2) are the same as or different from each other.

[0458] The plurality of G1in -Si(G1)(G1)(G2) are the same as or different from each other.

[0459] The plurality of G2in -Si(G2)(G2)(G2) are the same as or different from each other.

[0460] The plurality of G3in -Si(G3)(G3)(G3) are the same as or different from each other.

[0461] The plurality of G6in -Si(G6)(G6)(G6) are the same as or different from each other.

[0462] • the group represented by -O-(R 904 )

[0463] as the group represented by -O-(R 904Specific examples of the group represented by -O(G1) (specific example group G8) can include

[0464] -O(G1)、

[0465] -O(G2)、

[0466] -O(G3) and

[0467] -O(G6).

[0468] Here,

[0469] G1is "substituted or unsubstituted aryl" described in specific example group G1.

[0470] G2is "substituted or unsubstituted heterocyclic group" described in specific example group G2.

[0471] G3is "substituted or unsubstituted alkyl" described in specific example group G3.

[0472] G6is "substituted or unsubstituted cycloalkyl" described in specific example group G6.

[0473] • the group represented by -S-(R 905 ) represented in the present specification

[0474] Specific examples of the group represented by -S-(R 905 ) represented in the present specification (specific example group G9) can include

[0475] -S(G1)、

[0476] -S(G2)、

[0477] -S(G3) and

[0478] -S(G6).

[0479] Here,

[0480] G1is "substituted or unsubstituted aryl" described in specific example group G1.

[0481] G2is "substituted or unsubstituted heterocyclic group" described in specific example group G2.

[0482] G3is "substituted or unsubstituted alkyl" described in specific example group G3.

[0483] G6is "substituted or unsubstituted cycloalkyl" described in specific example group G6.

[0484] • the group represented by -N(R 906 )(R 907 ) represented in the present specification

[0485] Specific examples of the group represented by -N(R906 )(R 907 ) are shown as specific examples (specific example group G10), and the following are examples:

[0486] -N(G1)(G1),

[0487] -N(G2)(G2),

[0488] -N(G1)(G2),

[0489] -N(G3)(G3) and

[0490] -N(G6)(G6).

[0491] Here,

[0492] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0493] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0494] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0495] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0496] - A plurality of G1s in N(G1)(G1) are the same as or different from each other.

[0497] - The multiple G2s in N(G2)(G2) are the same as or different from each other.

[0498] - The multiple G3s in N(G3)(G3) are the same as or different from each other.

[0499] - A plurality of G6's in N(G6)(G6) are the same as or different from each other.

[0500] "Halogen atoms"

[0501] Specific examples of the "halogen atom" described in this specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0502] "Substituted or unsubstituted fluoroalkyl"

[0503] The "substituted or unsubstituted fluoroalkyl group" described in this specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). The number of carbon atoms in the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification. The "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of the "fluoroalkyl group" are replaced with a substituent. It should be noted that the "substituted fluoroalkyl group" described in this specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in the "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced with fluorine atoms.

[0504] "Substituted or unsubstituted haloalkyl"

[0505] The “substituted or unsubstituted haloalkyl group” described in this specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the “substituted or unsubstituted alkyl group” is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the “substituted or unsubstituted alkyl group” are replaced with halogen atoms. The number of carbon atoms in the “unsubstituted haloalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification. The “substituted haloalkyl group” refers to a group in which one or more hydrogen atoms of the “haloalkyl group” are replaced with a substituent. It should be noted that the “substituted haloalkyl group” described in this specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the “substituted haloalkyl group” are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in the “substituted haloalkyl group” are further replaced with a substituent. Specific examples of "unsubstituted haloalkyl groups" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl groups" (specific example group G3) are replaced with halogen atoms. A haloalkyl group is sometimes referred to as a halogenated alkyl group.

[0506] "Substituted or unsubstituted alkoxy"

[0507] As a specific example of the "substituted or unsubstituted alkoxy group" recited in the present specification, a group represented by -O(G3) is exemplified, in which G3 is the "substituted or unsubstituted alkyl group" recited in the specific example group G3. The carbon number of the "unsubstituted alkoxy group" is, unless otherwise specified in the present specification, 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0508] • "Substituted or unsubstituted alkylthio group"

[0509] As a specific example of the "substituted or unsubstituted alkylthio group" recited in the present specification, a group represented by -S(G3) is exemplified, in which G3 is the "substituted or unsubstituted alkyl group" recited in the specific example group G3. The carbon number of the "unsubstituted alkylthio group" is, unless otherwise specified in the present specification, 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0510] • "Substituted or unsubstituted aryloxy group"

[0511] As a specific example of the "substituted or unsubstituted aryloxy group" recited in the present specification, a group represented by -O(G1) is exemplified, in which G1 is the "substituted or unsubstituted aryl group" recited in the specific example group G1. The ring-constituting carbon number of the "unsubstituted aryloxy group" is, unless otherwise specified in the present specification, 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0512] • "Substituted or unsubstituted arylthio group"

[0513] As a specific example of the "substituted or unsubstituted arylthio group" recited in the present specification, a group represented by -S(G1) is exemplified, in which G1 is the "substituted or unsubstituted aryl group" recited in the specific example group G1. The ring-constituting carbon number of the "unsubstituted arylthio group" is, unless otherwise specified in the present specification, 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0514] • "Substituted or unsubstituted trialkylsilyl group"

[0515] As a specific example of the "trialkylsilyl group" recited in the present specification, a group represented by -Si(G3)(G3)(G3) is exemplified, in which G3 is the "substituted or unsubstituted alkyl group" recited in the specific example group G3. The plurality of G3 in -Si(G3)(G3)(G3) are the same or different from each other. The carbon number of each alkyl group of the "tralkylsilyl group" is, unless otherwise specified in the present specification, 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0516] • "Substituted or unsubstituted aralkyl group"

[0517] As a specific example of the "substituted or unsubstituted aralkyl group" recited in the present specification, a group represented by -(G3)-(Gl) is exemplified, wherein G3 is the "substituted or unsubstituted alkyl group" recited in the specific example group G3, and Gl is the "substituted or unsubstituted aryl group" recited in the specific example group Gl. Thus, the "aralkyl group" is a group in which the hydrogen atom of the "alkyl group" is replaced with the "aryl group" as a substituent, and is one of the "substituted alkyl groups". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with the "unsubstituted aryl group", and the carbon number of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in the present specification.

[0518] As a specific example of the "substituted or unsubstituted aralkyl group", benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-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, and the like can be exemplified.

[0519] The substituted or unsubstituted aryl group recited in the present specification is preferably a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, and the like, unless otherwise specified in the present specification.

[0520] ​The substituted or unsubstituted heterocyclic group described in the present specification is preferably, unless otherwise specified in the present specification, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, quinazolyl, benzimidazolyl, phenanthrolinyl, carbazolyl (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl or 9-carbazolyl), benzocarbazolyl, azacarbazolyl, diazacarbazolyl, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophenyl, naphthobenzothiophenyl, azadibenzothiophenyl, diazadibenzothiophenyl, (9-phenyl)carbazolyl ((9-phenyl)carbazol-1-yl, (9-phenyl)carbazol-2-yl, (9-phenyl)carbazol-3-yl or (9-phenyl)carbazol-4-yl), (9-biphenyl)carbazolyl, (9-phenyl)phenylcarbazolyl, diphenylcarbazol-9-yl, phenylcarbazol-9-yl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenyldibenzofuranyl and phenyldibenzothiophenyl, and the like.

[0521] In the present specification, the carbazolyl is specifically, unless otherwise specified in the present specification, any one of the following groups.

[0522] [Chemical Formula 21]

[0523]

[0524] In the present specification, the (9-phenyl)carbazolyl is specifically, unless otherwise specified in the present specification, any one of the following groups.

[0525] [Chemical Formula 22]

[0526]

[0527] In the above general formulae (TEMP-Cz1) to (TEMP-Cz9), * indicates a bonding position.

[0528] In the present specification, the dibenzofuranyl and dibenzothiophenyl are specifically, unless otherwise specified in the present specification, any one of the following groups.

[0529] [Chemical Formula 23]

[0530]

[0531] In the above general formulae (TEMP-34) to (TEMP-41), * indicates a bonding position.

[0532] The substituted or unsubstituted alkyl group described in the present specification is preferably, unless otherwise specified in the present specification, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl and t-butyl, and the like.

[0533] "Substituted or unsubstituted arylene group"

[0534] Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted aryl group" by removing one hydrogen atom from the aryl ring. Specific examples of the "substituted or unsubstituted arylene 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.

[0535] "Substituted or unsubstituted divalent heterocyclic group"

[0536] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom from the heterocyclic ring. Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (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 heterocyclic ring.

[0537] "Substituted or unsubstituted alkylene"

[0538] Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted alkyl group" by removing one hydrogen atom from the alkyl chain. Specific examples of the "substituted or unsubstituted alkylene group" (Specific Example Group G14) include divalent groups derived from the "substituted or unsubstituted alkyl group" described in Specific Example Group G3 by removing one hydrogen atom from the alkyl chain.

[0539] The substituted or unsubstituted arylene group described in the present specification is preferably any one of the following general formulae (TEMP-42) to (TEMP-68) unless otherwise described in the present specification.

[0540] [Chemical Formula 24]

[0541]

[0542] [Chemical Formula 25]

[0543]

[0544] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 are each independently a hydrogen atom or a substituent.

[0545] In the above general formulas (TEMP-42) to (TEMP-52), * represents a bonding position.

[0546] [Chemical Formula 26]

[0547]

[0548] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent.

[0549] Formula Q9 and Q 10 They may be bonded to each other via a single bond to form a ring.

[0550] In the above general formulas (TEMP-53) to (TEMP-62), * represents a bonding position.

[0551] [Chemical Formula 27]

[0552]

[0553] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0554] In the above general formulas (TEMP-63) to (TEMP-68), * represents a bonding position.

[0555] Unless otherwise described in the present specification, the substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the following general formulae (TEMP-69) to (TEMP-102).

[0556] [Chemical Formula 28]

[0557]

[0558] [Chemical Formula 29]

[0559]

[0560] [Chemical formula 30]

[0561]

[0562] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0563] [Chemical Formula 31]

[0564]

[0565] [Chemical Formula 32]

[0566]

[0567] [Formula 33]

[0568]

[0569] [Formula 34]

[0570]

[0571] In General Formulae (TEMP-83) to (TEMP-102) above, Q1to Q8are each independently a hydrogen atom or a substituent.

[0572] The above is a description of the "substituent described in the present specification".

[0573] • "case where 1 or more groups of 2 or more adjacent groups are bonded to form a substituted or unsubstituted monocyclic ring, or are bonded to form a substituted or unsubstituted fused ring, or are not bonded to each other"

[0574] In the present specification, the expression "1 or more groups of 2 or more adjacent groups are bonded to form a substituted or unsubstituted monocyclic ring, or are bonded to form a substituted or unsubstituted fused ring, or are not bonded to each other" means the case where "1 or more groups of 2 or more adjacent groups are bonded to form a substituted or unsubstituted monocyclic ring", the case where "1 or more groups of 2 or more adjacent groups are bonded to form a substituted or unsubstituted fused ring", and the case where "1 or more groups of 2 or more adjacent groups are not bonded to each other".

[0575] Hereinafter, the case where "1 or more groups of 2 or more adjacent groups are bonded to form a substituted or unsubstituted monocyclic ring" and the case where "1 or more groups of 2 or more adjacent groups are bonded to form a substituted or unsubstituted fused ring" (hereinafter, these cases are sometimes collectively referred to as "case where bonded to form a ring") in the present specification will be described. The case of an anthracene compound represented by the following General Formula (TEMP-103) in which the parent skeleton is an anthracene ring will be described.

[0576] [Formula 35]

[0577]

[0578] For example, in the case where "1 or more groups of 2 or more adjacent groups are bonded to form a ring" among R 921 to R 930 , the group of 2 adjacent groups that become 1 group means the group of R 921 and R 922 , the group of R 922 and R 923 , the group of R 923 and R 924 , the group of R 924 and R 930R 930 R 925 R 925 R 926 R 926 R 927 R 927 R 928 R 928 R 929 R 929 R 921 R

[0579] The "one or more groups" above means that two or more groups consisting of two or more adjacent groups can form a ring at the same time. For example, when R 921 and R 922 are bonded to each other to form a ring Q A , and at the same time, R 925 and R 926 are bonded to each other to form a ring Q B , the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0580] [Chemical Formula 36]

[0581]

[0582] The case where the "one or more groups consisting of two or more adjacent groups" form a ring includes not only the case where the bonding occurs in the group consisting of "two" adjacent groups as in the aforementioned example, but also the case where the bonding occurs in the group consisting of "three or more" adjacent groups. For example, it means that R 921 and R 922 are bonded to each other to form a ring Q A , and R 922 and R 923 are bonded to each other to form a ring Q C , the bonding occurs in the group consisting of three groups (R 921 , R 922 , and R 923 ) adjacent to each other, and the ring is fused to the anthracene parent skeleton, in which case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the general formula (TEMP-105) below, the ring Q A and the ring Q C share R 922 .

[0583] [Chemical Formula 37]

[0584]

[0585] In the formed "monocyclic ring" or "condensed ring", the structure of the formed ring itself may be a saturated ring or an unsaturated ring. Even when "one of the two adjacent groups" forms a "monocyclic ring" or "condensed ring", the "monocyclic ring" or "condensed ring" may form a saturated ring or an unsaturated ring. For example, in the above-mentioned general formula (TEMP-104), the ring Q A and Ring Q B Each is a "monocyclic" or "condensed ring". In addition, the ring Q formed in the above general formula (TEMP-105) A and Ring Q C The ring Q of the above general formula (TEMP-105) is A With Ring Q C Through Ring Q A With Ring Q C The ring Q of the above general formula (TMEP-104) is fused to form a fused ring. A If it is a benzene ring, then ring Q A The ring Q of the above general formula (TMEP-104) is A If it is a naphthalene ring, then ring Q A It is a fused ring.

[0586] The "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.

[0587] Specific examples of the aromatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G1 are terminated with hydrogen atoms.

[0588] Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified in Specific Example Group G2 are terminated with hydrogen atoms.

[0589] Specific examples of the aliphatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G6 are terminated with hydrogen atoms.

[0590] "Forming a ring" means that a ring is formed only by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton and one or more other optional elements. For example, R 921 With R 922 The ring Q formed by mutual bonding A Refers to R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 The carbon atom of the anthracene skeleton to which the bonding occurs forms a ring with one or more optional elements. 921 With R 922 Formation of ring Q A In the case of R921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 When the carbon atom of the anthracene skeleton to which the carbon atom is bonded forms a monocyclic unsaturated ring with four carbon atoms, R 921 With R 922 The ring formed is a benzene ring.

[0591] Here, "optional element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur, as long as it is not otherwise described in this specification. In the optional element (for example, in the case of carbon or nitrogen), the bond that does not form a ring can be terminated by a hydrogen atom or the like, or can be substituted by an "optional substituent" described later. When an optional element other than carbon is included, the ring formed is a heterocycle.

[0592] Unless otherwise specified in the present specification, the number of "one or more optional elements" constituting a monocyclic or condensed ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.

[0593] Unless otherwise specified in the present specification, "monocyclic ring" is preferred among "monocyclic ring" and "condensed ring".

[0594] In this specification, unless otherwise specified, among "saturated ring" and "unsaturated ring", "unsaturated ring" is preferred.

[0595] Unless otherwise specified in the present specification, a "monocyclic ring" is preferably a benzene ring.

[0596] Unless otherwise specified in this specification, the "unsaturated ring" is preferably a benzene ring.

[0597] In the case of "one or more groups consisting of two or more adjacent groups" "bonded to each other to form a substituted or unsubstituted monocyclic ring" or "bonded to each other to form a substituted or unsubstituted condensed ring", unless otherwise specified in this specification, it is preferred that one or more groups consisting of two or more adjacent groups bonded to each other to form a substituted or unsubstituted "unsaturated ring" formed by multiple atoms of the parent skeleton and one or more and fifteen or less elements selected from the group consisting of carbon, nitrogen, oxygen and sulfur.

[0598] When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, the "optional substituent" described below. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the above-mentioned section "Substituents described in the present specification".

[0599] The substituents in the case where the above-mentioned "saturated ring" or "unsaturated ring" has a substituent are, for example, the "optional substituent" described later. The specific examples of the substituents in the case where the above-mentioned "monocyclic ring" or "fused ring" has a substituent are the substituents described in the item of "substituents described in the present specification" above.

[0600] The above is the explanation of the case where "one or more of the groups consisting of 2 or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more of the groups consisting of 2 or more adjacent groups are bonded to each other to form a substituted or unsubstituted fused ring" ("the case where bonding to form a ring occurs").

[0601] • Substituents in the case where the expression "substituted or unsubstituted" is used

[0602] In one embodiment of the present specification, the above-mentioned substituents in the case where the expression "substituted or unsubstituted" is used (in the present specification, sometimes referred to as "optional substituent") are, for example, a group selected from the group consisting of

[0603] unsubstituted alkyl group having a carbon number of 1 to 50,

[0604] unsubstituted alkenyl group having a carbon number of 2 to 50,

[0605] unsubstituted alkynyl group having a carbon number of 2 to 50,

[0606] unsubstituted cycloalkyl group having a ring-forming carbon number of 3 to 50,

[0607] -Si(R 901 )(R 902 )(R 903 ),

[0608] -O-(R 904 ),

[0609] -S-(R 905 ),

[0610] -N(R 906 )(R 907 ),

[0611] halogen atom, cyano group, nitro group,

[0612] unsubstituted aryl group having a ring-forming carbon number of 6 to 50, and

[0613] unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50

[0614] and the like,

[0615] Here, R 901 to R 907 are each independently

[0616] a hydrogen atom,

[0617] substituted or unsubstituted alkyl having a carbon number of 1 to 50,

[0618] substituted or unsubstituted cycloalkyl having a ring-forming carbon number of 3 to 50,

[0619] substituted or unsubstituted aryl having a ring-forming carbon number of 6 to 50, or

[0620] substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50.

[0621] in R 901 in the case where two or more exist, two or more of R 901 are the same or different from each other,

[0622] in R 902 in the case where two or more exist, two or more of R 902 are the same or different from each other,

[0623] in R 903 in the case where two or more exist, two or more of R 903 are the same or different from each other,

[0624] in R 904 in the case where two or more exist, two or more of R 904 are the same or different from each other,

[0625] in R 905 in the case where two or more exist, two or more of R 905 are the same or different from each other,

[0626] in R 906 in the case where two or more exist, two or more of R 906 are the same or different from each other,

[0627] in R 907 in the case where two or more exist, two or more of R 907 are the same or different from each other.

[0628] In one embodiment, the substituent in the above expression "substituted or unsubstituted" is a group selected from the group consisting of

[0629] alkyl having a carbon number of 1 to 50,

[0630] aryl having a ring-forming carbon number of 6 to 50, and

[0631] heterocyclic group having a ring-forming atom number of 5 to 50.

[0632]

[0633] ​In one embodiment, the substituent in the case where the above expression "substituted or unsubstituted" is a group selected from the group consisting of

[0634] alkyl group having a carbon number of 1 to 18,

[0635] aromatic group having a ring-forming carbon number of 6 to 18, and

[0636] heterocyclic group having a ring-forming atom number of 5 to 18

[0637]

[0638] Specific examples of each group of the above optional substituent are the specific examples of the substituents described in the above item of "substituents described in the present specification".

[0639] In the present specification, unless otherwise specified, "saturated ring" or "unsaturated ring" can be formed by adjacent optional substituents to each other, preferably substituted or unsubstituted saturated five-membered ring, substituted or unsubstituted saturated six-membered ring, substituted or unsubstituted unsaturated five-membered ring, or substituted or unsubstituted unsaturated six-membered ring, more preferably benzene ring.

[0640] In the present specification, unless otherwise specified, the optional substituent can further have a substituent. As the substituent further having the optional substituent, the same as the above optional substituent.

[0641] In the present specification, the numerical range represented by "AA to BB" means a range including the lower limit value of the numerical value AA recited in the front of "AA to BB" and the upper limit value of the numerical value BB recited in the rear of "AA to BB".

[0642] Hereinafter, the compound of the present application will be described.

[0643] In one aspect of the present application, the compound of the present application is represented by the above formula (A). In another aspect of the present application, the compound of the present application is represented by the above formula (B) and contains at least one deuterium atom. In still another aspect of the present application, the compound of the present application is represented by formula (B'). Hereinafter, the symbols in formula (A) or (B) or (B') and the following described formulae contained in formula (A) or (B) or (B') will be described. Unless otherwise specified, the same symbols have the same meanings.

[0644] The compound of the present application represented by formula (A) or (B) or (B') and the following described formulae contained in formula (A) or (B) or (B') is sometimes referred to as "inventive compound".

[0645] The 1st compound of the present application (inventive compound (A)) is represented by the following formula (A).

[0646] [Chemical Formula 38]​

[0647]

[0648] In formula (A),

[0649] N* is the central nitrogen atom.

[0650] k is 0 or 1.

[0651] When k is 0, select R a1 ~R a6 One of the following, preferably R a4 or R a6 is a single bond bonded to *x.

[0652] When k is 1, R a1 With R a2 、R a2 With R a3 、R a3 With R a4 、R a5 With R a6 、R a7 With R a8 , or R a9 With R a10 One of, preferably R a1 With R a2 、R a3 With R a4 , or R a9 With R a10 One of them is a single bond bonded to *a, and the other is a single bond bonded to *b,

[0653] In the selection of R a1 With R a2 、R a2 With R a3 、R a3 With R a4 , and R a5 With R a6 When one of the groups is a single bond bonded to *a and the other is a single bond bonded to *b, R is selected from the group that is not a single bond bonded to *a and *b. a1 ~R a6 , and R a11 ~R a14 One of them is a single bond to *x,

[0654] In the selection of R a7 With R a8 , and R a9 With R a10 When one of the groups is a single bond bonded to *a and the other is a single bond bonded to *b, R a1one of R a6 is a single bond to *x.

[0655] In one embodiment of the present application, k is preferably 0.

[0656] R which is not a single bond to *x and also not a single bond to *a and *b a1 R a10 , and R which is not a single bond to *x a11 R a14 each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50, preferably 1 to 20, more preferably 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50, preferably 3 to 20, more preferably 3 to 6 ring-forming carbon atoms, or a halogen atom.

[0657] R which is not a single bond to *x and also not a single bond to *a and *b a1 R a10 , and R which is not a single bond to *x a11 R a14 Details of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms represented by R are the same as those described in the item of "substituent described in the present specification" above.

[0658] The unsubstituted alkyl group is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, or a t-butyl group, more preferably a methyl group, an isopropyl group, or a t-butyl group.

[0659] R which is not a single bond to *x and also not a single bond to *a and *b a1 R a10 , and R which is not a single bond to *x a11 R a14 Details of the substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms represented by R are the same as those described in the item of "substituent described in the present specification" above.

[0660] The unsubstituted cycloalkyl group is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, or an adamantyl group.

[0661] R which is not a single bond to *x and also not a single bond to *a and *b a1 R a10 , and R which is not a single bond to *x a11 R a14 Details of the halogen atom represented by R are the same as those described in the item of "substituent described in the present specification" above, and are preferably a fluorine atom.

[0662] R which is not a single bond to *x and also not a single bond to *a and *b a1 Ra10 R can each be a hydrogen atom, and R a11 ~R a14 R can each be a hydrogen atom.

[0663] R selected from R a11 ~R a14 The 2 adjacent ones in R

[0664] R a21 ~R a24 R is a hydrogen atom.

[0665] X a1 X is an oxygen atom, or a sulfur atom, preferably an oxygen atom.

[0666] L a1 ~L a4 Each independently is a single bond or represented by the following formulae (i) to (iii).

[0667] [Chemical Formula 39]

[0668]

[0669] R selected from R 1 ~R 5 One of R

[0670] R selected from R 11 ~R 15 One of R 16 ~R 20 The other one of R

[0671] R selected from R 21 ~R 28 One of R 21 ~R 28 The other one of R

[0672] In one aspect of the present application, R 3 is preferably a single bond to *2.

[0673] In one aspect of the present application, it is preferred that R 13 is a single bond to *3, and R 16 is a single bond to *6.

[0674] R other than the above single bond, R 1 ~R 5 R other than the above single bond, R 11 ~R 20 R other than the above single bond,21 ~R 28 each independently is a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbons, preferably 1 to 20, more preferably 1 to 6, an unsubstituted alkenyl group having 2 to 50 carbons, preferably 2 to 20, more preferably 2 to 6, an unsubstituted alkynyl group having 2 to 50 carbons, preferably 2 to 20, more preferably 2 to 6, an unsubstituted cycloalkyl group having 3 to 50 ring-forming carbons, preferably 3 to 20, more preferably 3 to 6, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring-forming carbons, preferably 6 to 30, more preferably 6 to 18, or an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, preferably 5 to 30, more preferably 5 to 18,

[0675] R 901 ~R 905 each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbons, preferably 1 to 20, more preferably 1 to 6, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbons, preferably 3 to 20, more preferably 3 to 6, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbons, preferably 6 to 30, more preferably 6 to 18, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, preferably 5 to 30, more preferably 5 to 18,

[0676] in the case where two or more R 901 are present, the two or more R 901 are the same or different from each other,

[0677] in the case where two or more R 902 are present, the two or more R 902 are the same or different from each other,

[0678] in the case where two or more R 903 are present, the two or more R 903 are the same or different from each other,

[0679] in the case where two or more R 904 are present, the two or more R 904 are the same or different from each other,

[0680] in the case where two or more R 905 are present, the two or more R 905 are the same or different from each other.

[0681] in the case where two or more R 1 are present, the two or more R5 R which is not the above single bond 11 R which is not the above single bond 20 R which is not the above single bond 21 R which is not the above single bond 28 The details of the unsubstituted alkyl group having a carbon number of 1 to 50 represented by R which is not the above single bond

[0682] The unsubstituted alkyl group is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, or a t-butyl group, and more preferably a methyl group, an isopropyl group, or a t-butyl group.

[0683] R which is not the above single bond 1 R which is not the above single bond 5 R which is not the above single bond 11 R which is not the above single bond 20 R which is not the above single bond 21 R which is not the above single bond 28 The details of the unsubstituted alkenyl group having a carbon number of 2 to 50 represented by R which is not the above single bond

[0684] R which is not the above single bond 1 R which is not the above single bond 5 R which is not the above single bond 11 R which is not the above single bond 20 R which is not the above single bond 21 R which is not the above single bond 28 The details of the unsubstituted alkynyl group having a carbon number of 2 to 50 represented by R which is not the above single bond

[0685] R which is not the above single bond 1 R which is not the above single bond 5 R which is not the above single bond 11 R which is not the above single bond 20 R which is not the above single bond 21 R which is not the above single bond 28 The details of the unsubstituted cyclic alkyl group having a ring-forming carbon number of 3 to 50 represented by R which is not the above single bond

[0686] The unsubstituted cyclic alkyl group is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, or an adamantyl group.

[0687] R which is not the above single bond 1 R which is not the above single bond 5 R which is not the above single bond 11 R which is not the above single bond 20 R which is not the above single bond 21 R which is not the above single bond 28 The details of the halogen atom represented by R which is not the above single bond are the same as those described in the item of "substituent described in the present specification" above, and are preferably a fluorine atom.

[0688] R which is not the above single bond 1 ~R 5 R which is not the above single bond 11 ~R 20 R which is not the above single bond 21 ~R 28 The details of the unsubstituted aryl group having 6 to 50 ring-forming carbons represented by R which is not the above single bond are the same as those described in the item of "substituent described in the present specification" above.

[0689] The unsubstituted aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a fluorenyl group.

[0690] R which is not the above single bond 21 ~R 23 R which is not the above single bond 24 R which is not the above single bond 25 The details of the unsubstituted heterocyclic group having 5 to 50 ring-forming atoms represented by R which is not the above single bond are the same as those described in the item of "substituent described in the present specification" above.

[0691] The unsubstituted heterocyclic group is preferably a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.

[0692] R which is not the above single bond 901 ~R 905 The details of the substituted or unsubstituted alkyl group having 1 to 50 carbons represented by R which is not the above single bond are the same as those described in the item of "substituent described in the present specification" above.

[0693] The unsubstituted alkyl group is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, or a tert-butyl group, more preferably a methyl group, an isopropyl group, or a tert-butyl group.

[0694] R which is not the above single bond 901 ~R 905 The details of the substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbons represented by R which is not the above single bond are the same as those described in the item of "substituent described in the present specification" above.

[0695] The unsubstituted cycloalkyl group is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, or an adamantyl group.

[0696] R which is not the above single bond 901 ~R 905 The details of the substituted or unsubstituted aryl group having 6 to 50 ring-forming carbons represented by R which is not the above single bond are the same as those described in the item of "substituent described in the present specification" above.

[0697] The unsubstituted aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

[0698] R which is not the above single bond 901 ~R 905Details of the substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms are the same as those described in the item of "substituent described in the present specification" above.

[0699] The unsubstituted heterocyclic group is preferably dibenzofuranyl, dibenzothiophenyl, or carbazolyl.

[0700] R 1 ~R 5 R 11 ~R 20 R 21 ~R 28 R

[0701] *1, *4, and *8 indicate the bonding position to the central nitrogen atom N*, or *x,

[0702] *3, *7, and *11 indicate the bonding position to Ar a1 , Ar a2 , or the benzene ring A.

[0703] Two adjacent ones selected from R 1 ~R 5 , R 11 ~R 20 , and R 21 ~R 28 may be bonded to each other to form a substituted or unsubstituted ring structure.

[0704] The unsubstituted monocyclic ring formed by two adjacent ones selected from R 1 ~R 5 , R 11 ~R 20 , and R 21 ~R 28 is, for example, a benzene ring, a cyclopentane ring, or a cyclohexane ring.

[0705] The unsubstituted fused ring formed by two adjacent ones selected from R 1 ~R 5 , R 11 ~R 20 , and R 21 ~R 28 is, for example, a naphthalene ring or an anthracene ring.

[0706] L a1 is preferably a single bond or represented by the above formula (i).

[0707] La2 is preferably a single bond or represented by the above formula (i).

[0708] L a3 is preferably a single bond or represented by the above formula (i), and more preferably a single bond.

[0709] L a4 is preferably a single bond or represented by the above formula (i), and more preferably a single bond.

[0710] Ar a1 and Ar a2 each independently represented by the following formulae (a) to (f).

[0711] [Chemical Formula 40]

[0712]

[0713] in formula (a),

[0714] *21 is a bonding position to L a1 or L a2 .

[0715] selected from R 101 to R 105 is a single bond to *22, and one selected from R 106 to R 110 is a single bond to *23.

[0716] R 101 to R 105 and R 106 to R 110 each independently are a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbons, or an unsubstituted aryl group having 6 to 12 ring-forming carbons.

[0717] adjacent two selected from R 101 to R 105 other than the above single bond do not bond to each other without forming a ring.

[0718] adjacent two selected from R 106 to R 110 other than the above single bond do not bond to each other without forming a ring.

[0719] R 101 to R 105 and R 106 to R 110The unsubstituted alkyl group having 1 to 10 carbon atoms represented by is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, or decyl, preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl, more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, further preferably methyl or tert-butyl, and particularly preferably tert-butyl.

[0720] R is not a single bond as mentioned above 101 ~R 105 and R 106 ~R 110 The unsubstituted aryl group having 6 to 12 ring carbon atoms represented by is, for example, phenyl, biphenyl, or naphthyl, preferably phenyl, 2-biphenyl, 3-biphenyl, or 4-biphenyl, or 1-naphthyl or 2-naphthyl, more preferably phenyl, 1-naphthyl, or 2-naphthyl, and particularly preferably phenyl.

[0721] R 111 ~R 115 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.

[0722] Selected from R 111 ~R 115 The two adjacent ones in the molecule are not bonded to each other and do not form a ring.

[0723] The above R 111 ~R 115 The details and preferred examples of the unsubstituted C1-10 alkyl group are the same as those described above for R other than the single bond. 101 ~R 105 and R 106 ~R 110 The records are the same.

[0724] The above R 111 ~R 115 The details and preferred examples of the unsubstituted aryl group having 6 to 12 ring carbon atoms are the same as those described above for R other than the single bond. 101 ~R 105 and R 106 ~R 110 The records are the same.

[0725] The above R 111 ~R 115The unsubstituted heterocyclic group having 5 to 13 ring-forming carbon atoms represented by the formula (A) is, for example, a pyrrolyl group, a furanyl group, a thienyl group, a pyridyl group, an imidazopyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a pyrazolyl group, an isoxazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a tetrazolyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolizyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazyl group, a quinazolyl group, a quinoxalyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, an indazolyl group, a benzisoxazolyl group, a benzisothiazolyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a benzothienyl group (same below), an isobenzothienyl group (same below), a dibenzothienyl group (same below), or a carbazolyl group, preferably a pyrrolyl group, a furanyl group, a thienyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolyl group, a benzimidazolyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a benzothienyl group, an isobenzothienyl group, a dibenzothienyl group, or a carbazolyl group, more preferably a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a benzothienyl group, an isobenzothienyl group, a dibenzothienyl group, or a carbazolyl group (9-carbazolyl group, or a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, or a 4-carbazolyl group).

[0726] The substituted heterocyclic group having 5 to 13 ring-forming atoms is, for example, a 9-phenylcarbazolyl group, a 9-biphenylcarbazolyl group, a 9-phenylphenylcarbazolyl group, a 9-naphthylcarbazolyl group, a phenyldibenzofuranyl group, or a phenyldibenzothienyl group (same below).

[0727] The above-mentioned substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms includes an isomeric group when present.

[0728] R 101 R 105 R 106 R 110 R 111 R 115 R

[0729] m is 0, 1, or 2, and n is 0 or 1.

[0730] In the case where m = 0 and n = 0, *23 represents *21.

[0731] In the case where m = 0 and n = 1, *22 represents *21.

[0732] In the case where m = 1 and n = 0, *23 represents *22.

[0733] In one aspect of the present application, m is 0 and n is 0. In this case, *23 represents *21, and formula (a) is represented by the following formula.

[0734] [Chemical Formula 41]

[0735]

[0736] In another aspect of the present application, m is 0 and n is 1. In this case, *22 represents *21, and formula (a) is represented by the following formula.

[0737] [Chemical Formula 42]

[0738]

[0739] In another aspect of the present application, m is 1 and n is 0. In this case, *23 represents *22, and formula (a) is represented by the following formula.

[0740] [Chemical Formula 43]

[0741]

[0742] In another aspect of the present application, m is 1 and n is 1. In this case, formula (a) is represented by the following formula.

[0743] [Chemical Formula 44]

[0744]

[0745] In another aspect of the present application, m is 2 and n is 0. In this case, *23 represents *22, and formula (a) is represented by the following formula.

[0746] [Chemical Formula 45]

[0747]

[0748] In another aspect of the present application, m is 2 and n is 1. In this case, formula (a) is represented by the following formula.

[0749] [Chemical Formula 46]

[0750]

[0751] The group represented by formula (a) is preferably represented by the following formula. In the following formula, R is omitted for simplicity.

[0752] R is the same as the above R 101 ~ R 105 and R 106 ~ R 110 , or R 111 ~ R115 the same.

[0753] [Chemical Formula 47]

[0754]

[0755] where, in formula (A), in the case where k is 0, R a5 is a single bond, L a1 , L a3 and L a4 are single bonds, Ar a1 represents m+n in formula (a) is 0, 1 or 3,

[0756] in the case where k is 0, R a5 is a single bond, L a3 and L a4 are single bonds, L a1 in formula (i), Ar a1 represents m+n in formula (a) is 0, 2 or 3,

[0757] in the case where k is 0, R a5 is a single bond, L a3 and L a4 are single bonds, L a1 in formula (i), Ar a1 represents m+n in formula (a) is 1, 2 or 3.

[0758] [Chemical Formula 48]

[0759]

[0760] in formula (b),

[0761] *24 is a bonding position to L a1 or L a2 .

[0762] one selected from R 121 to R 128 is a single bond to *25.

[0763] R 121 to R 128 other than the above single bond are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having a carbon number of 1 to 10, or a substituted or unsubstituted aromatic group having a ring-constituting carbon number of 6 to 12.

[0764] adjacent 2 selected from R 121 to R 128 other than the above single bond do not bond to each other to form a ring.

[0765] R121 ~R 128 The details of the unsubstituted alkyl group having 1 to 10 carbons represented by R 101 ~R 105 and R 106 ~R 110 are the same as described above for R

[0766] R 121 ~R 128 The details of the unsubstituted aryl group having 6 to 12 ring-forming carbons represented by R 101 ~R 105 and R 106 ~R 110 are the same as described above for R

[0767] In one aspect of the present application, it is preferable that one of R 121 , R 124 , R 125 , and R 128 be a single bond to *25.

[0768] R 121 ~R 128 may each independently be a hydrogen atom.

[0769] [Chemical Formula 49]

[0770]

[0771] In formula (c),

[0772] *26 is the bonding position to L a1 or L a2 .

[0773] One of R 131 ~R 140 is a single bond to *27.

[0774] R 131 ~R 140 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbons, or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbons.

[0775] Two adjacent ones of R 131 ~R 140 selected from R a5 ~R a1 may not be bonded to each other to form a ring.

[0776] wherein, in formula (A), R a5 is a single bond to *x, L a1 ~La4 In the case of a single bond, R 131 、R 132 、R 134 、R 135 , and R 137 ~R 140 One of them is a single bond to *27.

[0777] R is not a single bond as mentioned above 131 ~R 140 The details and preferred examples of the unsubstituted C1-10 alkyl group are the same as those described above for R other than the single bond. 101 ~R 105 and R 106 ~R 110 The records are the same.

[0778] R is not a single bond as mentioned above 131 ~R 140 The details and preferred examples of the unsubstituted aryl group having 6 to 12 ring carbon atoms are the same as those described above for R other than the single bond. 101 ~R 105 and R 106 ~R 110 The records are the same.

[0779] In one embodiment of the present invention, it is preferred that R 137 、R 138 and R 139 One of them is a single bond to *27, more preferably, selected from R 137 and R 139 One of them is a single bond bonded to *27, and more preferably, R 139 is a single bond bonded to *27.

[0780] R that is not a single bond to *27 131 ~R 140 They may all be hydrogen atoms.

[0781] [Chemical Formula 50]

[0782]

[0783] In formula (d),

[0784] *28 is with L a1 or L a2 bonding position.

[0785] X 11 For oxygen atoms, sulfur atoms, CR A R B or NR C .

[0786] R A and R B Each of them is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30, preferably 1 to 18, more preferably 1 to 10, and even more preferably 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50, preferably 3 to 18, more preferably 3 to 10, and even more preferably 3 to 6 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 18, and even more preferably 6 to 12 ring carbon atoms. They may be bonded to each other to form a substituted or unsubstituted ring structure, or may not be bonded to each other to form no ring.

[0787] The above R A The unsubstituted alkyl group having 1 to 30 carbon atoms represented by RB is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, or dodecyl, preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, or pentyl, more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, further preferably methyl, ethyl, isopropyl, or tert-butyl, and particularly preferably methyl.

[0788] The above R A The unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms represented by RB is, for example, cyclopropyl, cyclopentyl, cyclohexyl, or cyclooctyl, and preferably cyclohexyl or cyclooctyl.

[0789] The above R A and RB are unsubstituted aryl groups having 6 to 30 ring carbon atoms, for example, phenyl, biphenyl, terphenyl, biphenylenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, triphenylenyl, phenanthrenyl, pyrenyl, pentaphenanthrenyl, pyrenyl, Benzo The present invention is characterized in that the present invention is characterized in that the present invention can be used as an organic group or an organic group, and the organic group can be used as an organic group. The organic group can be used as an organic group, and the organic group can be used as an organic group.

[0790] From the above R A Examples of the unsubstituted monocyclic ring formed with RB include a benzene ring, a cyclopentane ring, and a cyclohexane ring.

[0791] From the above R AExamples of the unsubstituted condensed ring formed with RB include a naphthalene ring and an anthracene ring.

[0792] In addition, in R A With R B When they are bonded to each other to form an unsubstituted monocyclic ring or an unsubstituted condensed ring, R A and R B These may form a spiro ring with the fluorene backbone to which they are bonded. These spiro rings are hydrocarbon or heterocyclic rings, selected from monocyclic, fused, bicyclic, and tricyclic bridged rings. Examples of substituted or unsubstituted spiro rings are shown below, but are not limited to these. * indicates the position of the bond to the benzene ring of the fluorene backbone.

[0793] [Chemical Formula 51]

[0794]

[0795] R C It is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30, preferably 1 to 18, more preferably 1 to 10, and even more preferably 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 18, and more preferably 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30, preferably 5 to 18, and more preferably 5 to 13 ring atoms.

[0796] The above R C The details and preferred examples of the unsubstituted alkyl group having 1 to 30 carbon atoms are the same as those described above for the above R A and R B The records are the same.

[0797] The above R C The details and preferred examples of the unsubstituted aryl group having 6 to 30 ring carbon atoms are the same as those described above for the above R A and R B The records are the same.

[0798] The above R CThe unsubstituted heterocyclic group having 5 to 30 ring carbon atoms represented by the present invention is exemplified by pyrrolyl, furanyl, thienyl, pyridyl, imidazopyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, indolyl, isoindolyl, indolizinyl, quinolizinyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, indazolyl, benzisoxazolyl, benzisothiazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, xanthenyl, benzofuranyl, isobenzofuranyl , naphthiobenzofuranyl, dibenzofuranyl, benzothienyl (benzothienyl, the same below), isobenzothienyl (isobenzothienyl, the same below), naphthiobenzothienyl (naphthobenzothienyl, the same below), dibenzothienyl (dibenzothienyl, the same below), or carbazolyl, preferably benzofuranyl, isobenzofuranyl, naphthiobenzofuranyl, dibenzofuranyl, benzothienyl, isobenzothienyl, naphthiobenzothienyl, dibenzothienyl, or carbazolyl (9-carbazolyl, or 1-carbazolyl, 2-carbazolyl, 3-carbazolyl or 4-carbazolyl).

[0799] l is 0 or 1.

[0800] When l is 0, select R A 、R B 、R C , and R 141 ~R 148 One of them is a single bond to *29, or R A or R B A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, R A or RB may be bonded to each other to form a substituted or unsubstituted ring structure, or R C The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms which may be represented is bonded to *29 via a single bond.

[0801] When l is 1, R 141 With R 142 、R 142 With R 143 , or R 143 With R 144 One of them is a single bond bonded to *c, and the other is a single bond bonded to *d, and R is selected from single bonds other than those bonded to *c and *d. 141 ~R 144 、R 145 ~R 148 、R A 、RB 、R C , and R 200 ~R 203 One of them is a single bond to *29, or R A or R B It may represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or R A or RB may be bonded to each other to form a substituted or unsubstituted ring structure, or R C The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms which may be represented is bonded to *29 via a single bond.

[0802] R is not a single bond as mentioned above 141 ~R 148 , and R other than the above single bond 200 ~R 203 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.

[0803] R is selected from the group consisting of 141 ~R 148 , and R other than the above single bond 200 ~R 203 The two adjacent ones in the molecule are not bonded to each other and do not form a ring.

[0804] R is not a single bond as mentioned above 141 ~R 148 and R 200 ~R 203 The details and preferred examples of the unsubstituted C1-10 alkyl group are the same as those described above for R other than the single bond. 101 ~R 105 and R 106 ~R 110 The records are the same.

[0805] R is not a single bond as mentioned above 141 ~R 148 and R 200 ~R 203 The details and preferred examples of the unsubstituted aryl group having 6 to 12 ring carbon atoms are the same as those described above for R other than the single bond. 101 ~R 105 and R 106 ~R 110 The records are the same.

[0806] R is not a single bond as mentioned above 141 ~R 148 and R 200 ~R 203Details of the unsubstituted heterocyclic group having 5 to 13 ring-forming atoms represented by and preferred examples thereof are the same as those described above for R 111 ~R 115 in the above.

[0807] R 141 ~R 148 may each be a hydrogen atom. R 200 ~R 203 may each be a hydrogen atom.

[0808] [Chemical Formula 52]

[0809]

[0810] In formula (e),

[0811] *30 is a bonding position with L a1 or L a2 .

[0812] One selected from R 151 ~R 155 is a single bond with *31, and the other selected from R 151 ~R 155 is a single bond with *32.

[0813] R 151 ~R 155 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbons, or an unsubstituted phenyl group.

[0814] Two adjacent ones selected from R 151 ~R 155 that are not single bonds are not bonded to each other and do not form a ring.

[0815] R 161 ~R 165 and R 171 ~R 175 are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbons.

[0816] Two adjacent ones of at least one pair selected from R 161 ~R 165 may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and thus do not form a ring.

[0817] Two adjacent ones of at least one pair selected from R 171 ~R 175 may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and thus do not form a ring.

[0818] R151 ~R 155 , R 161 ~R 165 and R 171 ~R 175 The details of the above unsubstituted alkyl group having a carbon number of 1 to 10 and its preferred examples represented by R 101 ~R 105 and R 106 ~R 110 are the same as those described above for R 161 ~R 165 .

[0819] In one aspect of the present application, two adjacent ones selected from R 161 ~R 165 are bonded to each other to form an unsubstituted benzene ring. In another aspect of the present application, two adjacent ones selected from R 171 ~R 175 are not bonded to each other to form a ring.

[0820] In one aspect of the present application, two adjacent ones selected from R 171 ~R 175 are bonded to each other to form an unsubstituted benzene ring. In another aspect of the present application, two adjacent ones selected from R 151 ~R 155 are not bonded to each other to form a ring.

[0821] R 161 ~R 165 may each independently be a hydrogen atom, an unsubstituted alkyl group having a carbon number of 1 to 10, or an unsubstituted aryl group having a carbon number of 6 to 12. 171 ~R 175 may each independently be a hydrogen atom.

[0822] [Chemical Formula 53]

[0823]

[0824] In formula (f),

[0825] *32 is a bonding position to L a1 or L a2 .

[0826] One selected from R 181 ~R 192 is a single bond to *33.

[0827] R 181 ~R 192 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having a carbon number of 1 to 10, or a substituted or unsubstituted aryl group having a carbon number of 6 to 12.

[0828] R is selected from the group consisting of 181 ~R 192 The two adjacent ones in the molecule are not bonded to each other and do not form a ring.

[0829] The above R 181 ~R 192 The details and preferred examples of the unsubstituted C1-10 alkyl group are the same as those described above for R other than the single bond. 101 ~R 105 and R 106 ~R 110 The records are the same.

[0830] The above R 181 ~R 192 The details and preferred examples of the unsubstituted aryl group having 6 to 12 ring carbon atoms are the same as those described above for R other than the single bond. 101 ~R 105 and R 106 ~R 110 The records are the same.

[0831] In one embodiment of the present invention, R 184 is a single bond to *33. In another embodiment, R 183 is a single bond bonded to *33.

[0832] R is not a single bond as mentioned above 181 ~R 192 They may all be hydrogen atoms.

[0833] In one embodiment of the present invention, Ar a1 It is preferably represented by the above formula (a), (b) or (c), and more preferably represented by the above formula (b).

[0834] In another embodiment of the present invention, Ar a1 It is preferably represented by the above-mentioned formula (d).

[0835] In one embodiment of the present invention, Ar a2 It is preferably represented by the above formula (a), (b) or (c), and more preferably represented by the above formula (b).

[0836] In another embodiment of the present invention, Ar a2 It is preferably represented by the above-mentioned formula (d).

[0837] In formula (A), L a1 and L a2 Phenylene, L a3 and L a4 is a single bond, Ar a1 and Ar a2 In the case represented by the above formula (b), La1 It is 1,2-phenylene or 1,4-phenylene.

[0838] The second compound of the present invention (inventive compound (B)) is represented by the following formula (B) and contains at least one deuterium atom. The third compound of the present invention (inventive compound (B')) is represented by the following formula (B').

[0839] [Chemical Formula 54]

[0840]

[0841] In formulas (B) and (B'),

[0842] N * The central nitrogen atom.

[0843] p is 0 or 1.

[0844] When p is 0, R b4 or R b6 is a single bond bonded to *y.

[0845] When p is 1, R b1 With R b2 、R b2 With R b3 、R b3 With R b4 、R b5 With R b6 、R b7 With R b8 、R b8 With R b9 , or R b9 With R b10 One of, preferably R b1 With R b2 、R b3 With R b4 , or R b9 With R b10 One of them is a single bond bonded to *e, and the other is a single bond bonded to *f,

[0846] In R b3 With R b4 When one of them is a single bond bonded to *e and the other is a single bond bonded to *f, R b6 is a single bond bonded to *y,

[0847] In R b5 With R b6 When one of them is a single bond bonded to *e and the other is a single bond bonded to *f, R b4 is a single bond bonded to *y,

[0848] In R b3 With R b4 , and R b5 With R b6 When one of them is not a single bond to *e and the other is not a single bond to *f, R b4 or R b6 is a single bond bonded to *y.

[0849] In one embodiment of the present invention, p is preferably 0.

[0850] R is not a single bond to *y and is not a single bond to *e and *f b1 ~R b10 , and R that is not a single bond to *y b11 ~R b14 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50, preferably 1 to 20, more preferably 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50, preferably 3 to 20, more preferably 3 to 6 ring carbon atoms, or a halogen atom.

[0851] R is not a single bond to *y and is not a single bond to *e and *f b1 ~R b10 , and R that is not a single bond to *y b11 ~R b14 The details and preferred examples of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms are the same as those for the single bond not bonded to *x and not bonded to *a and *b as described above. a1 ~R a10 , and R that is not a single bond to *x a11 ~R a14 The records are the same.

[0852] R is not a single bond to *y and is not a single bond to *e and *f b1 ~R b10 , and R that is not a single bond to *y b11 ~R b14 The details and preferred examples of the substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms are the same as those of R above for the single bond that is not bonded to *x and is not bonded to *a and *b. a1 ~R a10 , and R that is not a single bond to *x a11 ~R a14 The records are the same.

[0853] R is not a single bond to *y and is not a single bond to *e and *f b1 ~Rb10 R which is not a single bond to *y b11 ~R which is not a single bond to *y b14 R which is not a single bond to *x and also not to *a and *b a1 ~R which is not a single bond to *x and also not to *a and *b a10 R which is not a single bond to *x a11 ~R which is not a single bond to *x a14 R which is not a single bond to *x

[0854] R which is not a single bond to *y and also not to *e and *f b1 ~R which is not a single bond to *y and also not to *e and *f b10 R which is not a single bond to *y b11 ~R which is not a single bond to *y b14 R which is not a single bond to *y

[0855] R which is not a single bond to *y b11 ~R which is not a single bond to *y b14 The 2 adjacent ones in R

[0856] R which is not a single bond to *y b21 ~R which is not a single bond to *y b24 R which is not a single bond to *y

[0857] X b1 is an oxygen atom, or a sulfur atom, preferably an oxygen atom.

[0858] L b1 ~L b4 are each independently a single bond or represented by the following formulae (i) to (iii).

[0859] L in formulae (B) and (B′) b1 ~L b4 are each independently a single bond or represented by the following formulae (i) to (iii).

[0860] wherein, in formulae (i) to (iii), *1, *4, and *8 indicate the bonding position to the central nitrogen atom N * , or *y,

[0861] *3, *7, and *11 indicate the bonding position to Ar b1 , Ar b2 , or the benzene ring B.

[0862] L b1 is preferably a single bond or represented by the above formula (i).

[0863] L b2 is preferably a single bond or represented by the above formula (i).

[0864] L b3 is preferably a single bond or represented by the above formula (i), and more preferably a single bond.

[0865] L b4 is preferably a single bond or represented by the above formula (i), and more preferably a single bond.

[0866] Ar b1 and Ar b2 each independently represented by the above formulae (a) to (f).

[0867] Ar b1 and Ar b2 represented by formulae (a) to (f) are the same as defined in formula (A).

[0868] wherein, in formulae (B) and (B'), at least one selected from Ar b1 and Ar b2 is represented by formula (d), L b1 , L b3 and L b4 is a single bond, 1 is 0, X 11 is CR A R B , in the case where R 141 to R 148 is a single bond to *29.

[0869] In one aspect of the present application, Ar b1 is preferably represented by the above formula (a), (b) or (c), and more preferably the above formula (a).

[0870] In another aspect of the present application, Ar b1 is preferably represented by the above formula (d).

[0871] In one aspect of the present application, Ar b2 is preferably represented by the above formula (a), (b) or (c), and more preferably the above formula (a).

[0872] In another aspect of the present application, Ar b2 is preferably represented by the above formula (d).

[0873] In formulae (B) and (B'), in the case where L b1 to L b4 is a single bond, Ar b1 is represented by formula (a) or (c) to (f), and in the case where Ar b1 is formula (a), m + n is 1, 2 or 3.

[0874] As described above, "a hydrogen atom" used in the present specification includes a protium atom, a deuterium atom and a tritium atom. The inventive compound can contain a deuterium atom of a natural source.

[0875] In addition, deuterium atoms can be intentionally introduced into the inventive compound by using a deuterated compound for a part or all of the starting compounds. Therefore, in one aspect of the present application, the inventive compound contains at least one deuterium atom. That is, the inventive compound can also be a compound represented by formula (A) in which at least one of the hydrogen atoms contained therein is a deuterium atom, or a compound represented by formula (B) in which at least one of the hydrogen atoms contained therein is a deuterium atom.

[0876] At least one of the hydrogen atoms selected from the group consisting of the hydrogen atoms represented by any one of the groups of R

[0877] R of formula (A) a1 R of formula (A) a10 R of formula (A) a11 R of formula (A) a14 R of formula (A)

[0878] R of formula (A) a1 R of formula (A) a10 R of formula (A) a11 R of formula (A) a14 R of formula (A)

[0879] R of formula (A) a21 R of formula (A) a24 R of formula (A)

[0880] L of formula (A) a1 L of formula (A) a4 L of formula (A)

[0881] Ar of formula (A) a1 Ar of formula (A) a2 Ar of formula (A)

[0882] At least one of the hydrogen atoms selected from the group consisting of the hydrogen atoms represented by any one of the groups of R

[0883] R of formula (B) b1 R of formula (B) b10 R of formula (B) b11 R of formula (B) b14 R of formula (B)

[0884] R of formula (B) b1 ~R b10 , and R b11 ~R b14 when any one of R of formula (B)

[0885] R of formula (B) b21 ~R b24 represents a hydrogen atom;

[0886] L of formula (B) b1 ~L b4 represents a hydrogen atom of formula (i) to (iii);

[0887] Ar of formula (B) b1 and Ar b2 represents a hydrogen atom of formula (a) to (f).

[0888] The deuterium enrichment of the compound of the present application depends on the deuterium enrichment of the starting compound used. Even if a starting compound having a specified deuterium enrichment is used, it can contain a certain proportion of protium isotopes of natural origin. Therefore, for the deuterium enrichment of the compound of the present application, the proportion calculated by counting only the number of deuterium atoms represented in the chemical formula includes the ratio of the trace amount of isotopes taking into account the natural origin.

[0889] The deuterium enrichment of the compound of the present application is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, still further preferably 10% or more, and still further preferably 50% or more.

[0890] The compound of the present application can be a mixture containing a compound that has been deuterated and a compound that has not been deuterated, a mixture of two or more compounds having different deuterium enrichments. The deuterium enrichment of such a mixture is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, still further preferably 10% or more, and still further preferably 50% or more, and less than 100%.

[0891] In addition, the proportion of the number of deuterium atoms to the total number of hydrogen atoms in the compound of the present application is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, still further preferably 10% or more, and 100% or less.

[0892] When the "substituted or unsubstituted XX group" included in the definitions of the above formulas is a substituted XX group, the details of the substituent are the same as those described in "Substituents when the term "substituted or unsubstituted" is used." Preferably, it is an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring carbon atoms, or a heterocyclic group having 5 to 13 ring atoms (heteroaryl group), and more preferably an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 12 ring carbon atoms. The details of each group (alkyl group, aryl group, heterocyclic group) are the same as above.

[0893] The compounds of the present invention can be easily produced by those skilled in the art with reference to the following synthesis examples and known synthesis methods.

[0894] Specific examples of the compounds of the invention are shown below, but the invention is not limited to the following exemplary compounds.

[0895] In the following specific examples, D represents a deuterium atom.

[0896] Exemplary compounds of formula (A)

[0897] [Chemical Formula 55]

[0898]

[0899] [Chemical Formula 56]

[0900]

[0901] [Chemical Formula 57]

[0902]

[0903] [Chemical Formula 58]

[0904]

[0905] [Chemical Formula 59]

[0906]

[0907] [Chemical Formula 60]

[0908]

[0909] [Chemical Formula 61]

[0910]

[0911] [Chemical Formula 62]

[0912]

[0913] [Chemical Formula 63]

[0914]

[0915] [Formula 64]

[0916]

[0917] [Formula 65]

[0918]

[0919] [Formula 66]

[0920]

[0921] [Formula 67]

[0922]

[0923] [Formula 68]

[0924]

[0925] [Formula 69]

[0926]

[0927] [Formula 70]

[0928]

[0929] [Formula 71]

[0930]

[0931] [Formula 72]

[0932]

[0933] [Formula 73]

[0934]

[0935] [Formula 74]

[0936]

[0937] [Formula 75]

[0938]

[0939] [Formula 76]

[0940]

[0941] [Formula 77]

[0942]

[0943] [Chemical Formula 78]

[0944]

[0945] [Chemical Formula 79]

[0946]

[0947] [Chemical Formula 80]

[0948]

[0949] [Chemical Formula 81]

[0950]

[0951] [Chemical Formula 82]

[0952]

[0953] [Chemical Formula 83]

[0954]

[0955] [Chemical Formula 84]

[0956]

[0957] [Chemical Formula 85]

[0958]

[0959] [Chemical Formula 86]

[0960]

[0961] [Chemical Formula 87]

[0962]

[0963] [Chemical Formula 88]

[0964]

[0965] [Chemical Formula 89]

[0966]

[0967] [Chemical Formula 90]

[0968]

[0969] [Chemical Formula 91]

[0970]

[0971] [Chemical Formula 92]

[0972]

[0973] [Chemical Formula 93]

[0974]

[0975] [Chemical Formula 94]

[0976]

[0977] [Chemical Formula 95]

[0978]

[0979] [Chemical Formula 96]

[0980]

[0981] [Chemical Formula 97]

[0982]

[0983] [Chemical Formula 98]

[0984]

[0985] [Chemical Formula 99]

[0986]

[0987] [Chemical Formula 100]

[0988]

[0989] [Chemical Formula 101]

[0990]

[0991] [Chemical Formula 102]

[0992]

[0993] [Chemical Formula 103]

[0994]

[0995] [Chemical Formula 104]

[0996]

[0997] [Chemical Formula 105]

[0998]

[0999] [Chemical Formula 106]

[1000]

[1001] [Chemical Formula 107]

[1002]

[1003] [Chemical Formula 108]

[1004]

[1005] [Chemical Formula 109]

[1006]

[1007] [Chemical Formula 110]

[1008]

[1009] [Chemical Formula 111]

[1010]

[1011] [Chemical Formula 112]

[1012]

[1013] [Chemical Formula 113]

[1014]

[1015] [Chemical Formula 114]

[1016]

[1017] [Chemical Formula 115]

[1018]

[1019] [Chemical Formula 116]

[1020]

[1021] [Chemical Formula 117]

[1022]

[1023] [Chemical Formula 118]

[1024]

[1025] [Chemical Formula 119]

[1026]

[1027] [Chemical Formula 120]

[1028]

[1029] [Chemical Formula 121]

[1030]

[1031] [Chemical Formula 122]

[1032]

[1033] [Chemical Formula 123]

[1034]

[1035] [Chemical Formula 124]

[1036]

[1037] [Chemical Formula 125]

[1038]

[1039] [Chemical Formula 126]

[1040]

[1041] [Chemical Formula 127]

[1042]

[1043] [Chemical Formula 128]

[1044]

[1045] [Chemical Formula 129]

[1046]

[1047] [Chemical Formula 130]

[1048]

[1049] [Chemical Formula 131]

[1050]

[1051] [Chemical Formula 132]

[1052]

[1053] [Chemical Formula 133]

[1054]

[1055] [Chemical Formula 134]

[1056]

[1057] [Chemical Formula 135]

[1058]

[1059] [Chemical Formula 136]

[1060]

[1061] [Chemical Formula 137]

[1062]

[1063] [Chemical Formula 138]

[1064]

[1065] [Chemical Formula 139]

[1066]

[1067] [Chemical Formula 140]

[1068]

[1069] [Chemical Formula 141]

[1070]

[1071] [Chemical Formula 142]

[1072]

[1073] [Chemical Formula 143]

[1074]

[1075] [Chemical formula 144]

[1076]

[1077] [Chemical Formula 145]

[1078]

[1079] [Chemical Formula 146]

[1080]

[1081] [Chemical Formula 147]

[1082]

[1083] [Chemical Formula 148]

[1084]

[1085] [Chemical Formula 149]

[1086]

[1087] [Chemical Formula 150]

[1088]

[1089] [Chemical Formula 151]

[1090]

[1091] [Chemical formula 152]

[1092]

[1093] [Chemical Formula 153]

[1094]

[1095] [Chemical formula 154]

[1096]

[1097] [Chemical formula 155]

[1098]

[1099] [Chemical formula 156]

[1100]

[1101] [Chemical Formula 157]

[1102]

[1103] [Chemical Formula 158]

[1104]

[1105] [Chemical Formula 159]

[1106]

[1107] [Chemical Formula 160]

[1108]

[1109] [Chemical Formula 161]

[1110]

[1111] [Chemical Formula 162]

[1112]

[1113] [Chemical Formula 163]

[1114]

[1115] [Chemical Formula 164]

[1116]

[1117] [Chemical Formula 165]

[1118]

[1119] [Chemical Formula 166]

[1120]

[1121] [Chemical Formula 167]

[1122]

[1123] [Chemical Formula 168]

[1124]

[1125] [Chemical Formula 169]

[1126]

[1127] [Chemical Formula 170]

[1128]

[1129] [Chemical Formula 171]

[1130]

[1131] [Chemical Formula 172]

[1132]

[1133] [Chemical Formula 173]

[1134]

[1135] [Chem. 174]

[1136]

[1137] [Chem. 175]

[1138]

[1139] [Chem. 176]

[1140]

[1141] [Chem. 177]

[1142]

[1143] [Chem. 178]

[1144]

[1145] [Chem. 179]

[1146]

[1147] [Chem. 180]

[1148]

[1149] [Chem. 181]

[1150]

[1151] [Chem. 182]

[1152]

[1153] [Chem. 183]

[1154]

[1155] [Chem. 184]

[1156]

[1157] [Chem. 185]

[1158]

[1159] [Chem. 186]

[1160]

[1161] [Chemical Formula 187]

[1162]

[1163] [Chemical Formula 188]

[1164]

[1165] [Chemical Formula 189]

[1166]

[1167] [Chemical Formula 190]

[1168]

[1169] [Chemical Formula 191]

[1170]

[1171] [Chemical Formula 192]

[1172]

[1173] [Chemical Formula 193]

[1174]

[1175] [Chemical Formula 194]

[1176]

[1177] [Chemical Formula 195]

[1178]

[1179] [Chemical Formula 196]

[1180]

[1181] [Chemical Formula 197]

[1182]

[1183] [Chemical Formula 198]

[1184]

[1185] [Chemical Formula 199]

[1186]

[1187] [Chemical Formula 200]

[1188]

[1189] [Formula 201]

[1190]

[1191] [Formula 202]

[1192]

[1193] [Formula 203]

[1194]

[1195] [Formula 204]

[1196]

[1197] [Formula 205]

[1198]

[1199] [Formula 206]

[1200]

[1201] [Formula 207]

[1202]

[1203] [Formula 208]

[1204]

[1205] [Formula 209]

[1206]

[1207] [Formula 210]

[1208]

[1209] [Formula 211]

[1210]

[1211] [Formula 212]

[1212]

[1213] [Formula 213]

[1214]

[1215] [Formula 214]

[1216]

[1217] [Chemical Formula 215]

[1218]

[1219] [Chemical Formula 216]

[1220]

[1221] [Chemical Formula 217]

[1222]

[1223] [Chemical Formula 218]

[1224]

[1225] [Chemical Formula 219]

[1226]

[1227] [Chemical Formula 220]

[1228]

[1229] [Chemical Formula 221]

[1230]

[1231] [Chemical Formula 222]

[1232]

[1233] [Chemical Formula 223]

[1234]

[1235] [Chemical Formula 224]

[1236]

[1237] [Chemical Formula 225]

[1238]

[1239] [Chemical Formula 226]

[1240]

[1241] [Chemical Formula 227]

[1242]

[1243] [Chemical Formula 228]

[1244]

[1245] [Chemical Formula 229]

[1246]

[1247] [Chemical Formula 230]

[1248]

[1249] [Chemical Formula 231]

[1250]

[1251] [Chemical formula 232]

[1252]

[1253] [Chemical formula 233]

[1254]

[1255] [Chemical formula 234]

[1256]

[1257] [Chemical Formula 235]

[1258]

[1259] [Chemical Formula 236]

[1260]

[1261] [Chemical Formula 237]

[1262]

[1263] [Chemical formula 238]

[1264]

[1265] [Chemical Formula 239]

[1266]

[1267] [Chemical Formula 240]

[1268]

[1269] [Chemical Formula 241]

[1270]

[1271] [Chemical Formula 242]

[1272]

[1273] [Chemical Formula 243]

[1274]

[1275] [Chemical Formula 244]

[1276]

[1277] Exemplary compounds of formulae (B) and (B')

[1278] [Chemical Formula 245]

[1279]

[1280] [Chemical Formula 246]

[1281]

[1282] [Chemical Formula 247]

[1283]

[1284] [Chemical Formula 248]

[1285]

[1286] [Chemical Formula 249]

[1287]

[1288] [Chemical Formula 250]

[1289]

[1290] [Chemical Formula 251]

[1291]

[1292] [Chemical Formula 252]

[1293]

[1294] [Chemical Formula 253]

[1295]

[1296] [Chemical Formula 254]

[1297]

[1298] [Chemical formula 255]

[1299]

[1300] [Chemical formula 256]

[1301]

[1302] [Chemical Formula 257]

[1303]

[1304] [Chemical formula 258]

[1305]

[1306] [Chemical Formula 259]

[1307]

[1308] [Chemical Formula 260]

[1309]

[1310] [Chemical Formula 261]

[1311]

[1312] [Chemical formula 262]

[1313]

[1314] [Chemical formula 263]

[1315]

[1316] [Chemical formula 264]

[1317]

[1318] [Chemical Formula 265]

[1319]

[1320] [Chemical Formula 266]

[1321]

[1322] [Chemical Formula 267]

[1323]

[1324] [Chemical Formula 268]

[1325]

[1326] [Chem. 269]

[1327]

[1328] [Chem. 270]

[1329]

[1330] [Chem. 271]

[1331]

[1332] [Chem. 272]

[1333]

[1334] [Chem. 273]

[1335]

[1336] [Chem. 274]

[1337]

[1338] [Chem. 275]

[1339]

[1340] [Chem. 276]

[1341]

[1342] [Chem. 277]

[1343]

[1344] [Chem. 278]

[1345]

[1346] [Chem. 279]

[1347]

[1348] [Chem. 280]

[1349]

[1350] [Chem. 281]

[1351]

[1352] [Chemical Formula 282]

[1353]

[1354] [Chemical Formula 283]

[1355]

[1356] [Chemical Formula 284]

[1357]

[1358] [Chemical Formula 285]

[1359]

[1360] [Chemical Formula 286]

[1361]

[1362] [Chemical Formula 287]

[1363]

[1364] [Chemical Formula 288]

[1365]

[1366] [Chemical Formula 289]

[1367]

[1368] [Chemical Formula 290]

[1369]

[1370] [Chemical Formula 291]

[1371]

[1372] [Chemical Formula 292]

[1373]

[1374] [Chemical Formula 293]

[1375]

[1376] [Chemical Formula 294]

[1377]

[1378] [Chemical Formula 295]

[1379]

[1380] [Chemical Formula 296]

[1381]

[1382] [Chemical Formula 297]

[1383]

[1384] [Chemical Formula 298]

[1385]

[1386] [Chemical Formula 299]

[1387]

[1388] [Chemical Formula 300]

[1389]

[1390] [Chemical Formula 301]

[1391]

[1392] [Chemical Formula 302]

[1393]

[1394] [Chemical Formula 303]

[1395]

[1396] [Chemical Formula 304]

[1397]

[1398] [Chemical Formula 305]

[1399]

[1400] [Chemical Formula 306]

[1401]

[1402] [Chemical Formula 307]

[1403]

[1404] [Chemical Formula 308]

[1405]

[1406] [Chemical Formula 309]

[1407]

[1408] [Chemical Formula 310]

[1409]

[1410] [Chemical Formula 311]

[1411]

[1412] [Chemical Formula 312]

[1413]

[1414] [Chemical Formula 313]

[1415]

[1416] [Chemical Formula 314]

[1417]

[1418] [Chemical Formula 315]

[1419]

[1420] [Chemical Formula 316]

[1421]

[1422] [Chemical Formula 317]

[1423]

[1424] [Chemical Formula 318]

[1425]

[1426] [Chemical Formula 319]

[1427]

[1428] [Chemical Formula 320]

[1429]

[1430] [Chemical Formula 321]

[1431]

[1432] [Chemical Formula 322]

[1433]

[1434] [Chemical Formula 323]

[1435]

[1436] [Chemical Formula 324]

[1437]

[1438] [Chemical Formula 325]

[1439]

[1440] [Chemical Formula 326]

[1441]

[1442] [Chemical Formula 327]

[1443]

[1444] [Chemical Formula 328]

[1445]

[1446] [Chemical Formula 329]

[1447]

[1448] [Chemical Formula 330]

[1449]

[1450] [Chemical Formula 331]

[1451]

[1452] [Chemical formula 332]

[1453]

[1454] [Chemical Formula 333]

[1455]

[1456] [Chemical formula 334]

[1457]

[1458] [Chemical Formula 335]

[1459]

[1460] [Chemical Formula 336]

[1461]

[1462] [Chemical Formula 337]

[1463]

[1464] [Chemical Formula 338]

[1465]

[1466] [Chemical Formula 339]

[1467]

[1468] [Chemical Formula 340]

[1469]

[1470] [Chemical Formula 341]

[1471]

[1472] [Chemical Formula 342]

[1473]

[1474] [Chemical Formula 343]

[1475]

[1476] [Chemical Formula 344]

[1477]

[1478] [Chemical Formula 345]

[1479]

[1480] [Chemical Formula 346]

[1481]

[1482] [Chemical Formula 347]

[1483]

[1484] [Chemical Formula 348]

[1485]

[1486] [Chemical Formula 349]

[1487]

[1488] [Chemical Formula 350]

[1489]

[1490] [Chemical Formula 351]

[1491]

[1492] [Chemical Formula 352]

[1493]

[1494] [Chemical Formula 353]

[1495]

[1496] [Chemical Formula 354]

[1497]

[1498] [Chemical Formula 355]

[1499]

[1500] [Chemical Formula 356]

[1501]

[1502] [Chemical Formula 357]

[1503]

[1504] [Chemical Formula 358]

[1505]

[1506] [Chemical Formula 359]

[1507]

[1508] [Chemical Formula 360]

[1509]

[1510] [Chemical Formula 361]

[1511]

[1512] [Chemical Formula 362]

[1513]

[1514] [Chemical Formula 363]

[1515]

[1516] [Formula 364]

[1517]

[1518] [Formula 365]

[1519]

[1520] [Formula 366]

[1521]

[1522] [Formula 367]

[1523]

[1524] [Formula 368]

[1525]

[1526] [Formula 369]

[1527]

[1528] Material for organic EL element

[1529] The material for organic EL element of the present application contains the inventive compound. The content of the inventive compound in the material for organic EL element is 1 mass% or more (including 100%), preferably 10 mass% or more (including 100%), more preferably 50 mass% or more (including 100%), further preferably 80 mass% or more (including 100%), particularly preferably 90 mass% or more (including 100%). The material for organic EL element of the present application is useful for the production of an organic EL element.

[1530] Organic EL element

[1531] In one aspect of the present application, the organic EL element of the present application contains an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer contains a light-emitting layer, and at least one layer of the organic layer contains the inventive compound.

[1532] In another aspect of the present application, the organic EL element of the present application contains an anode, a light-emitting layer, and a cathode, and contains an organic layer between the anode and the light-emitting layer, and at least one layer of the organic layer contains the inventive compound (B').

[1533] As examples of the organic layer containing the inventive compound, there can be mentioned a hole-transporting region (hole-injection layer, hole-transporting layer, electron-blocking layer, exciton-blocking layer, etc.) provided between the anode and the light-emitting layer, the light-emitting layer, the spacer layer, an electron-transporting region (electron-injection layer, electron-transporting layer, hole-blocking layer, etc.) provided between the cathode and the light-emitting layer, etc., but are not limited thereto. The inventive compound is preferably used as a material for the hole-transporting region or the light-emitting layer of a fluorescent or phosphorescent EL element, more preferably as a material for the hole-transporting region, further preferably as a material for the hole-injection layer, the hole-transporting layer, the electron-blocking layer, or the exciton-blocking layer, particularly preferably as a material for the hole-injection layer or the hole-transporting layer.

[1534] The organic EL element of the present application can be a single-color light-emitting element of a fluorescent or phosphorescent light-emitting type, a white light-emitting element of a fluorescent / phosphorescent hybrid type, a simple type having a single light-emitting unit, or a tandem type having a plurality of light-emitting units, and is preferably an element of a fluorescent light-emitting type. Here, the "light-emitting unit" refers to the smallest unit that contains an organic layer and in which at least one layer is a light-emitting layer and holes and electrons injected therein recombine to emit light.

[1535] For example, as a typical element configuration of a simple type organic EL element, the following element configurations can be mentioned.

[1536] (1) Anode / light-emitting unit / cathode

[1537] In addition, the light-emitting unit described above can also be a multi-layer type having a plurality of phosphorescent light-emitting layers or fluorescent light-emitting layers, and in this case, a spacer layer can be provided between the light-emitting layers for the purpose of preventing excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer. The following shows typical layer configurations of a simple type light-emitting unit. The layers in parentheses are optional.

[1538] (a) (Hole-injection layer) / hole-transporting layer / fluorescent light-emitting layer / electron-transporting layer (electron-injection layer)

[1539] (b) (Hole-injection layer) / hole-transporting layer / 1st fluorescent light-emitting layer / 2nd fluorescent light-emitting layer / electron-transporting layer (electron-injection layer)

[1540] (c) (Hole-injection layer) / hole-transporting layer / phosphorescent light-emitting layer / spacer layer / fluorescent light-emitting layer / electron-transporting layer (electron-injection layer)

[1541] (d) (Hole-injection layer) / hole-transporting layer / 1st phosphorescent light-emitting layer / 2nd phosphorescent light-emitting layer / spacer layer / fluorescent light-emitting layer / electron-transporting layer (electron-injection layer)

[1542] (e) (hole injection layer) / hole transport layer / phosphorescent light emitting layer / spacer layer / 1st fluorescent light emitting layer / 2nd fluorescent light emitting layer / electron transport layer (electron injection layer)

[1543] (f) (hole injection layer) / hole transport layer / electron blocking layer / fluorescent light emitting layer / electron transport layer (electron injection layer)

[1544] (g) (hole injection layer) / hole transport layer / exciton blocking layer / fluorescent light emitting layer / electron transport layer (electron injection layer)

[1545] (h) (hole injection layer) / 1st hole transport layer / 2nd hole transport layer / fluorescent light emitting layer / electron transport layer (electron injection layer)

[1546] (i) (hole injection layer) / 1st hole transport layer / 2nd hole transport layer / fluorescent light emitting layer / 1st electron transport layer / 2nd electron transport layer (electron injection layer)

[1547] (j) (hole injection layer) / hole transport layer / fluorescent light emitting layer / hole blocking layer / electron transport layer (electron injection layer)

[1548] (k) (hole injection layer) / hole transport layer / fluorescent light emitting layer / exciton blocking layer / electron transport layer (electron injection layer)

[1549] (I) (hole injection layer) / 1st hole transport layer / 2nd hole transport layer / 1st fluorescent light emitting layer / 2nd fluorescent light emitting layer / 1st electron transport layer / 2nd electron transport layer (electron injection layer)

[1550] (m) (hole injection layer) / 1st hole transport layer / 2nd hole transport layer / 3rd hole transport layer / 1st fluorescent light emitting layer / 2nd fluorescent light emitting layer / 1st electron transport layer / 2nd electron transport layer (electron injection layer)

[1551] (n) (hole injection layer) / 1st hole transport layer / 2nd hole transport layer / 3rd hole transport layer / fluorescent light emitting layer / 1st electron transport layer / 2nd electron transport layer (electron injection layer)

[1552] Each of the above phosphorescent or fluorescent light emitting layers can be provided as a light emitting layer that displays a mutually different emission color. Specifically, in the above light emitting unit (f), a layer configuration such as (hole injection layer) / hole transport layer / 1st phosphorescent light emitting layer (red emission) / 2nd phosphorescent light emitting layer (green emission) / spacer layer / fluorescent light emitting layer (blue emission) / electron transport layer can be cited.

[1553] Note that an electron-blocking layer (sometimes referred to as an electron barrier layer) can be provided as appropriate between each of the light-emitting layers and the hole-transport layer or the spacer layer. In addition, a hole-blocking layer can be provided as appropriate between each of the light-emitting layers and the electron-transport layer. By providing an electron-blocking layer or a hole-blocking layer, the recombination probability of charges in the light-emitting layer can be increased by confining electrons or holes in the light-emitting layer, and thus the emission efficiency can be increased.

[1554] In addition, the hole-transport layer adjacent to the light-emitting layer in a multilayer structure including two or more hole-transport layers, e.g., the second hole-transport layer in the above two-layer structure, the third hole-transport layer in the above three-layer structure, can also have a function as an electron-blocking layer. That is, in the case where the hole-transport layer is a multilayer structure including two or more hole-transport layers, the hole-transport layer adjacent to the light-emitting layer in the above multilayer structure can also function as an electron-blocking layer.

[1555] As a typical element structure of a tandem organic EL element, the following element structure can be given.

[1556] (2) anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode

[1557] Here, as the first light-emitting unit and the second light-emitting unit, each can be independently selected from the above light-emitting units, for example.

[1558] The above intermediate layer is also generally referred to as an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, an intermediate insulating layer, and can be formed using a known material that supplies electrons to the first light-emitting unit and holes to the second light-emitting unit.

[1559] Figure 1 is a schematic view showing an example of the structure of an organic EL element of the present application. The organic EL element 1 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 10 provided between the anode 3 and the cathode 4. The light-emitting unit 10 has a light-emitting layer 5. Between the light-emitting layer 5 and the anode 3, there is a hole-transport region 6 (a hole-injection layer, a hole-transport layer, or the like), and between the light-emitting layer 5 and the cathode 4, there is an electron-transport region 7 (an electron-injection layer, an electron-transport layer, or the like). 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. Thus, the generation efficiency of excitons in the light-emitting layer 5 can be further increased by confining electrons and holes in the light-emitting layer 5.

[1560] Figure 2is a schematic view showing another configuration of the organic EL element of the present application. The organic EL element 11 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 20 disposed between the anode 3 and the cathode 4. The light-emitting unit 20 has a light-emitting layer 5. A hole-transporting region disposed between the anode 3 and the light-emitting layer 5 is formed of a hole-injection layer 6a, a first hole-transporting layer 6b, and a second hole-transporting layer 6c. In addition, an electron-transporting region disposed between the light-emitting layer 5 and the cathode 4 is formed of a first electron-transporting layer 7a and a second electron-transporting layer 7b.

[1561] Figure 3 is a schematic view showing another configuration of the organic EL element of the present application. The organic EL element 12 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 30 disposed between the anode 3 and the cathode 4. The light-emitting unit 30 has a light-emitting layer 5. A hole-transporting region disposed between the anode 3 and the light-emitting layer 5 is formed of a hole-injection layer 6a, a first hole-transporting layer 6b, a second hole-transporting layer 6c, and a third hole-transporting layer 6d. In addition, an electron-transporting region disposed between the light-emitting layer 5 and the cathode 4 is formed of a first electron-transporting layer 7a and a second electron-transporting layer 7b.

[1562] Note that, in the present application, a host combined with a fluorescent dopant material (a fluorescent light-emitting material) is referred to as a fluorescent host, and a host combined with a phosphorescent dopant material is referred to as a phosphorescent host. The fluorescent host and the phosphorescent host are not distinguished only by molecular structure. That is, the phosphorescent host refers to a material forming a phosphorescent light-emitting layer containing a phosphorescent dopant, and does not mean that the material cannot be used as a material forming a fluorescent light-emitting layer. The same applies to the fluorescent host.

[1563] Substrate

[1564] The substrate serves as a support of the organic EL element. As the substrate, for example, a plate of glass, quartz, plastic, or the like can be used. In addition, a flexible substrate can be used. As the flexible substrate, for example, a plastic substrate formed of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyfluoroethylene, polyvinyl chloride, or the like can be given. In addition, an inorganic vapor deposition film can be used.

[1565] Anode

[1566] The anode formed on the substrate preferably uses a metal, an alloy, a conductive compound, and a mixture thereof, etc. having a large work function (specifically, 4.0 eV or more). Specifically, for example, indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, indium oxide containing tungsten oxide and zinc oxide, graphene, etc. can be given. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or a nitride of the above metal (for example, titanium nitride), etc. can be given.

[1567] These materials are generally formed into a film by a sputtering method. For example, indium zinc oxide can be formed by a sputtering method using a target in which 1 to 10 wt% of zinc oxide is added to indium oxide, and indium oxide containing tungsten oxide and zinc oxide can be formed by a sputtering method using a target in which 0.5 to 5 wt% of tungsten oxide and 0.1 to 1 wt% of zinc oxide are contained in indium oxide. In addition, it can also be produced by a vacuum evaporation method, a coating method, an inkjet method, a spin coating method, etc.

[1568] Hole transport region

[1569] As described above, the organic layer can include a hole transport region between the anode and the light-emitting layer. The hole transport region is composed of a hole injection layer, a hole transport layer, an electron blocking layer, etc. The hole transport region preferably includes the inventive compound. It is preferable that the inventive compound be included in at least one of these layers constituting the hole transport layer, and it is particularly more preferable that the inventive compound be included in the hole transport layer.

[1570] The hole injection layer formed adjacent to the anode is formed using a material that easily performs hole injection regardless of the work function of the anode, and thus a material generally used as an electrode material (for example, a metal, an alloy, a conductive compound, and a mixture thereof, an element belonging to Group 1 or Group 2 of the periodic table) can be used.

[1571] An element belonging to Group 1 or Group 2 of the periodic table, i.e., an alkali metal such as lithium (Li), cesium (Cs), and an alkaline earth metal such as magnesium (Mg), calcium (Ca), strontium (Sr), and an alloy containing the same (for example, MgAg, AlLi), a rare earth metal such as europium (Eu), ytterbium (Yb), and an alloy containing the same, etc. can also be used as a material having a small work function. Note that, when the anode is formed using an alkali metal, an alkaline earth metal, and an alloy containing the same, a vacuum evaporation method, a sputtering method, etc. can be used. In addition, when silver paste, etc. is used, a coating method, an inkjet method, etc. can be used.

[1572] Hole injection layer

[1573] The hole injection layer is a layer containing a material having high hole-injection property (hole-injection material) and is formed between the anode and the light-emitting layer or between the hole-transport layer and the anode when the hole-transport layer is present.

[1574] As the hole-injection material 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, and the like can be used.

[1575] As the hole-injection layer material, 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), and the like aromatic amine compounds, which are low molecular organic compounds, can be given.

[1576] Polymer compounds (oligomers, dendrimers, polymers, and the like) can also be used. For example, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD), and the like polymer compounds can be given. In addition, poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly(styrenesulfonic acid) (PAni / PSS), and the like polymer compounds to which an acid is added can be used.

[1577] Further, a compound represented by the following formula (K) or the like acceptor material is preferably used.

[1578] [Chemical Formula 370]

[1579]

[1580] (in the above formula, R 221 ~R 226 each independently represents a cyano group, -CONH2, a carboxyl group, or -COOR 227 (R 227 represents an alkyl group having 1 to 20 carbons or a cycloalkyl group having 3 to 20 carbons). In addition, 2 adjacent ones selected from R 221 and R 222 , R 223 and R 224 , and R 225 and R 226 may be bonded to each other to form a group represented by -CO-O-CO-.

[1581] As R 227 , a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a t-butyl group, a cyclopentyl group, a cyclohexyl group, and the like can be given.

[1582] Hole transport layer

[1583] The hole transport layer is a layer containing a material having high hole transport property (hole transport material), and is formed between the anode and the light-emitting layer, or between the hole injection layer and the light-emitting layer in the case where the hole injection layer is present. The inventive compound can be used in the hole transport layer alone or in combination with the following compounds.

[1584] The hole transport layer can be a single layer structure, or a multi-layer structure containing 2 or more layers. For example, the hole transport layer can be a 2-layer structure containing a first hole transport layer (anode side) and a second hole transport layer (cathode side). That is, the above hole transport region can contain the first hole transport layer on the anode side and the second hole transport layer on the cathode side. In addition, the hole transport layer can be a 3-layer structure containing the first hole transport layer, the second hole transport layer, and a third hole transport layer in this order from the anode side. That is, the third hole transport layer can be disposed between the second hole transport layer and the light-emitting layer.

[1585] In one aspect of the present application, the hole transport layer of the above single layer structure is preferably adjacent to the light-emitting layer, and in addition, the hole transport layer closest to the cathode in the above multi-layer structure, for example, the second hole transport layer in the above 2-layer structure or the third hole transport layer in the above 3-layer structure, is preferably adjacent to the light-emitting layer. In another aspect of the present application, an electron blocking layer or the like described later can be interposed between the hole transport layer of the above single layer structure and the light-emitting layer, or between the hole transport layer closest to the light-emitting layer in the above multi-layer structure and the light-emitting layer.

[1586] In the case where the hole-transport layer is a 2-layer structure, at least one of the first hole-transport layer and the second hole-transport layer contains the inventive compound. That is, the inventive compound is contained only in the first hole-transport layer, only in the second hole-transport layer, or in both the first hole-transport layer and the second hole-transport layer.

[1587] In one aspect of the present application, the inventive compound is preferably contained in the second hole-transport layer. That is, the inventive compound is preferably contained only in the second hole-transport layer, or the inventive compound is contained in the first hole-transport layer and the second hole-transport layer.

[1588] In the case where the hole-transport layer is a 3-layer structure, at least one of the first to third hole-transport layers contains the inventive compound. That is, the inventive compound is contained in only one layer selected from the first to third hole-transport layers (only the first hole-transport layer, only the second hole-transport layer, or only the third hole-transport layer), in only two layers selected from the first to third hole-transport layers (only the first and second hole-transport layers, only the first and third hole-transport layers, or only the second and third hole-transport layers), or in all of the first to third hole-transport layers.

[1589] In one aspect of the present application, the inventive compound is preferably contained in the third hole-transport layer. That is, the inventive compound is preferably contained only in the third hole-transport layer, or the inventive compound is contained in the third hole-transport layer and one or both of the first hole-transport layer and the second hole-transport layer.

[1590] In one aspect of the present application, the inventive compound contained in each of the above hole-transport layers is preferably a protium body from the viewpoint of manufacturing cost. The above protium body means an inventive compound in which all hydrogen atoms in the inventive compound are protium atoms.

[1591] Therefore, the present application includes an organic EL element in which one or both of the first hole-transport layer and the second hole-transport layer (in the case of a 2-layer structure) contains an inventive compound formed substantially only from a protium body, and an organic EL element in which at least one layer among the first to third hole-transport layers contains an inventive compound formed substantially only from a protium body. The meaning of "an inventive compound formed substantially only from a protium body" means that the content ratio of a protium body is 90 mol% or more, preferably 95 mol% or more, and more preferably 99 mol% or more (including 100% respectively) with respect to the total amount of the inventive compound.

[1592] As a hole-transport layer material other than the inventive compound, for example, an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used.

[1593] As the aromatic amine compound, for example, 4,4'-bis[N-(l-naphthyl)-N- phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'- diphenyl-[l,l'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9- phenylfluorene-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9- dimethylfluorene-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'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) can be given. The above compounds have a hole-transport property higher than an electron-transport property. -6 cm 2 a hole mobility of 10-6cmVsor more.

[1594] As the carbazole derivative, for example, 4,4'-di(9-carbazolyl) biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA) can be given.

[1595] As the anthracene derivative, for example, 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and 9,10-diphenylanthracene (abbreviation: DPAnth) can be given.

[1596] A high molecular compound such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), or the like can also be used.

[1597] Note that a compound other than the above can be used as long as it is a compound having a hole-transport property higher than an electron-transport property.

[1598] In the organic EL element having the 2-layer structure of the hole-transport layer according to the present application, it is preferable that the first hole-transport layer contain one or two or more kinds of compounds represented by the following formula (11) or formula (12).

[1599] In the organic EL element having the 3-layer structure of the hole-transport layer according to the present application, it is preferable that one or both of the first hole-transport layer and the second hole-transport layer contain one or two or more kinds of compounds represented by the following formula (11) or formula (12).

[1600] In the organic EL element having the n-layer structure (n is an integer of 4 or more) of the hole transport layer of the present application, at least one layer of the first to (n-1)th hole transport layers preferably contains one or two or more compounds represented by the following formula (11) or (12).

[1601] [Chemical Formula 371]

[1602]

[1603] [In the above formula (11) and (12),

[1604] L A1 , L B1 , L C1 , L A2 , L B2 , L C2 , and L D2 each independently is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms,

[1605] k is 1, 2, 3, or 4,

[1606] in the case where k is 1, L E2 is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms,

[1607] in the case where k is 2, 3, or 4, 2, 3, or 4 L E2 are the same as or different from each other,

[1608] in the case where k is 2, 3, or 4, a plurality of L E2 are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other,

[1609] L E2 which does not form the above monocyclic ring and does not form the above fused ring, is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms,

[1610] A 1 , B 1 , C 1 , A 2 , B 2 , C 2 , and D 2 each independently is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, or -Si(R' 901 )(R'902 )(R′ 903 ),

[1611] R′ 901 , R′ 902 and R′ 903 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1612] In R′ 901 When there are multiple R' 901 Same or different from each other,

[1613] In R′ 902 When there are multiple R' 902 Same or different from each other,

[1614] In R′ 903 When there are multiple R' 903 Same as or different from each other.]

[1615] In formula (11) and formula (12), it is preferred that A 1 、B 1 、C 1 、A 2 、B 2 、C 2 and D 2 Each is independently selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, and a substituted or unsubstituted carbazolyl group.

[1616] In addition, it is more preferred that A in formula (11) 1 、B 1 and C 1 At least one of them, and A in formula (12) 2 、B 2 、C 2 and D 2 At least one of them is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group.

[1617] A 1 、B 1 、C 1 、A 2 、B 2 、C 2 and D 2The fluorenyl group may have a substituent at position 9, such as 9,9-dimethylfluorenyl or 9,9-diphenylfluorenyl. Furthermore, the substituents at position 9 may form a ring, such as a fluorene skeleton or a xanthene skeleton.

[1618] L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 Preferably, each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.

[1619] Specific examples of the compounds represented by formula (11) and formula (12) include the following compounds.

[1620] [Chemical Formula 372]

[1621]

[1622] Dopant material for the light-emitting layer

[1623] The light-emitting layer is a layer containing a highly luminescent material (dopant material), and various materials can be used. For example, fluorescent materials or phosphorescent materials can be used as dopant materials. Fluorescent materials are compounds that emit light in a singlet excited state, while phosphorescent materials are compounds that emit light in a triplet excited state.

[1624] In one embodiment of the organic EL device according to the present invention, the light-emitting layer may be a single layer.

[1625] In another embodiment of the organic EL device according to the present invention, the light-emitting layer may include a first light-emitting layer and a second light-emitting layer.

[1626] As the blue fluorescent material that can be used for the light-emitting layer, pyrene derivatives, styrylamine derivatives, Derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. Specific examples include N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthracenyl)triphenylamine (abbreviation: YGAPA), and 4-(10-phenyl-9-anthracenyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA).

[1627] As a fluorescent light emitting material of the green color system which can be used for the light emitting layer, an aromatic amine derivative or the like can be used. Specifically, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-diaminobenzene (abbreviation: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-diaminobenzene (abbreviation: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), and the like can be given.

[1628] As a fluorescent light emitting material of the red color system which can be used for the light emitting layer, a tetracene derivative, a diamine derivative, or the like can be used. Specifically, N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), and the like can be given.

[1629] In one embodiment of the present application, it is preferable that the light emitting layer contain a fluorescent light emitting material (fluorescent dopant material).

[1630] As a phosphorescent light emitting material of the blue color system which can be used for the light emitting layer, a metal complex such as an iridium complex, an osmium complex, a platinum complex, or the like can be used. Specifically, bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) tetra(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviation: FIrpic), bis[2-(3',5'bis(trifluoromethyl)phenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviation: Ir(CF3ppy)2(pic)), bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) acetylacetonate (abbreviation: FIracac), and the like can be given.

[1631] Green phosphorescent materials that can be used in the light-emitting layer include iridium complexes. 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]quinolinol)iridium(III) acetylacetonate (abbreviated as Ir(bzq)2(acac)).

[1632] As red phosphorescent materials that can be used in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes can be used. Specifically, organic metal complexes such as bis[2-(2′-benzo[4,5-α]thienyl)pyridinium-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)), (acetylacetonato)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-porphyrinplatinum(II) (abbreviated as PtOEP) can be used.

[1633] In addition, rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviated as: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedione)(monophenanthroline)europium(III) (abbreviated as: Eu(DBM)3(Phen)), and tris[1-(2-thiophenoyl)-3,3,3-trifluoroacetonate](monophenanthroline)europium(III) (abbreviated as: Eu(TTA)3(Phen)) can be used as phosphorescent materials because the luminescence comes from rare earth metal ions (electron transitions between different multiplicities).

[1634] Host material of the light-emitting layer

[1635] The light-emitting layer may be a structure in which the dopant material is dispersed in another material (host material). Preferably, a material is used whose lowest unoccupied molecular orbital (LUMO) energy level is higher than that of the dopant material and whose highest occupied molecular orbital (HOMO) energy level is lower than that of the dopant material.

[1636] As the main material, for example,

[1637] (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes,

[1638] (2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives,

[1639] (3) fused aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or fluoranthene derivatives,

[1640] (4) aromatic amine compounds such as triarylamine derivatives or fused polycyclic aromatic amine derivatives.

[1641] For example, metal complexes such as tris(8-hydroxyquinoline)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-hydroxyquinolinate)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), and the like can be used.

[1642] 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2',2"-(1,3,5-benzene-triyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), and the like heterocyclic compounds;

[1643] 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,9'-bianthracene (abbreviation: BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviation: DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviation: DPNS2), 3,3',3"-(benzene-1,3,5-triyl)triphenylamine (abbreviation: TPB3), 9,10-diphenylanthracene (abbreviation: DPAnth), 6,12-dimethoxy-5,11-diphenyl Condensed aromatic compound; and

[1644] N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), and the like aromatic amine compounds. Two or more kinds of host materials can be used.

[1645] Especially, in the case of a blue fluorescent element, it is preferable to use the anthracene compound described below as a host material.

[1646] [Chemical Formula 373]

[1647]

[1648] [Chemical Formula 374]

[1649]

[1650] [Chemical Formula 375]

[1651]

[1652] In one embodiment of the organic EL element according to the present application, in the case where the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, at least one of the components included in the first light-emitting layer is different from the components included in the second light-emitting layer. For example, there are an embodiment in which the dopant material included in the first light-emitting layer is different from the dopant material included in the second light-emitting layer, and an embodiment in which the host material included in the first light-emitting layer is different from the host material included in the second light-emitting layer.

[1653] In the organic EL element of the present application, the light-emitting layer can contain a luminescent compound that exhibits fluorescent light emission with a main peak wavelength of 500 nm or less (hereinafter, sometimes referred to simply as "fluorescent light-emitting compound").

[1654] The method for measuring the main peak wavelength of a compound is described below. A 5 μmol / L toluene solution of the compound to be measured is prepared and added to a quartz cuvette, and the luminescence spectrum of the sample is measured at room temperature (300 K) (the vertical axis is set to the luminescence intensity, and the horizontal axis is set to the wavelength). The luminescence spectrum can be measured by a spectrofluorophotometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the luminescence spectrum measuring device is not limited to the device used here.

[1655] In the luminescence spectrum, the peak wavelength of the luminescence spectrum at which the luminescence intensity is the greatest is set to the main peak wavelength. Note that in this specification, the main peak wavelength is sometimes referred to as the fluorescent light emission main peak wavelength (FL-peak).

[1656] The above-described fluorescent light-emitting compound can be the above-described dopant material, or can be the above-described host material.

[1657] In the case where the light-emitting layer is a single layer, only one of the dopant material and the host material can be the above-described fluorescent light-emitting compound, or both can be the above-described fluorescent light-emitting compound.

[1658] In addition, in the case where the light-emitting layer includes a first light-emitting layer (anode side) and a second light-emitting layer (cathode side), only one of the first light-emitting layer and the second light-emitting layer can contain the above-described fluorescent light-emitting compound, or both can contain the above-described fluorescent light-emitting compound. In the case where the first light-emitting layer contains the above-described fluorescent light-emitting compound, only one of the dopant material and the host material contained in the first light-emitting layer can be the above-described fluorescent light-emitting compound, or both can be the above-described fluorescent light-emitting compound. In addition, in the case where the second light-emitting layer contains the above-described fluorescent light-emitting compound, only one of the dopant material and the host material contained in the second light-emitting layer can be the above-described fluorescent light-emitting compound, or both can be the above-described fluorescent light-emitting compound.

[1659] Electron transport region

[1660] The electron-transporting region is composed of an electron-injection layer, an electron-transporting layer, a hole-blocking layer, and the like. Any one of the layers in the electron-transporting region, particularly the electron-transporting layer, preferably contains one or more selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes containing alkali metals, organic complexes containing alkaline earth metals, and organic complexes containing rare earth metals.

[1661] The electron-transporting layer

[1662] The electron-transporting layer is a layer containing a material having high electron-transporting property (electron-transporting 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 case where the electron-injection layer is present.

[1663] The electron-transporting layer can be a single-layer structure or a multi-layer structure containing two or more layers. For example, the electron-transporting layer can be a two-layer structure containing a first electron-transporting layer (anode side) and a second electron-transporting layer (cathode side). In one embodiment of the present application, the electron-transporting layer of the above-described single-layer structure is preferably adjacent to the light-emitting layer, or the electron-transporting layer closest to the anode in the above-described multi-layer structure, for example, the first electron-transporting layer of the above-described two-layer structure, is preferably adjacent to the light-emitting layer. In another embodiment of the present application, a hole-blocking layer or the like described later can be interposed between the electron-transporting layer of the above-described single-layer structure and the light-emitting layer, or between the electron-transporting layer closest to the light-emitting layer in the above-described multi-layer structure and the light-emitting layer.

[1664] The electron-transporting layer can be formed using, for example,

[1665] (1) metal complexes such as aluminum complexes, beryllium complexes, zinc complexes, and the like,

[1666] (2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives, and the like,

[1667] (3) high molecular compounds.

[1668] As the metal complex, for example, tris(8-hydroxyquinoline)aluminum (III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum (III) (abbreviation: BAlq), bis(8-hydroxyquinolinate)zinc (II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc (II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc (II) (abbreviation: ZnBTZ) can be given.

[1669] As the heteroaromatic compound, for example, 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) can be given.

[1670] As the high molecular compound, for example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy) can be given.

[1671] The above material is a material having an electron mobility of 10 -6 cm 2 Vs or higher. Note that a material other than the above can be used for the electron transport layer as long as the material has higher electron transport property than hole transport property.

[1672] The electron injection layer

[1673] The electron injection layer is a layer containing a material having high electron injection property. As the electron injection layer, an alkali metal such as lithium (Li) or cesium (Cs), an alkaline earth metal such as magnesium (Mg), calcium (Ca), or strontium (Sr), a rare earth metal such as europium (Eu) or ytterbium (Yb), and a compound containing any of these metals can be used. As such a compound, for example, an alkali metal oxide, an alkali metal halide, an organic complex containing an alkali metal, an alkaline earth metal oxide, an alkaline earth metal halide, an organic complex containing an alkaline earth metal, a rare earth metal oxide, a rare earth metal halide, and an organic complex containing a rare earth metal can be given. Alternatively, a plurality of these compounds can be used in mixture.

[1674] Further, a material containing an alkali metal, an alkaline earth metal, or a compound thereof in a material having electron transport property can be used, and specifically, a material containing magnesium (Mg) in Alq can be used. Note that in this case, electron injection from the cathode can be performed more efficiently.

[1675] Alternatively, the electron injection layer can also use a composite material in which an organic compound and an electron donor (donor) are mixed. Such a composite material is excellent in electron injection and electron transport because the organic compound accepts electrons from the electron donor. At this time, as the organic compound, a material excellent in transport of the accepted electron is preferable, and specifically, for example, the above-described material (metal complex, heteroaromatic compound, etc.) that constitutes the electron transport layer can be used. As the electron donor, a material that exhibits electron-donating property to the organic compound is sufficient. Specifically, an alkali metal, an alkaline earth metal, and a rare earth metal are preferable, and lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like can be given. In addition, an alkali metal oxide, an alkaline earth metal oxide is preferable, and lithium oxide, calcium oxide, barium oxide, and the like can be given. In addition, a Lewis base such as magnesium oxide can also be used. In addition, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.

[1676] Cathode

[1677] The cathode preferably uses a metal, an alloy, a conductive compound, and a mixture thereof, or the like having a small work function (specifically, 3.8 eV or less). As specific examples of such a cathode material, an element belonging to Group 1 or Group 2 of the periodic table, i.e., an alkali metal such as lithium (Li) and cesium (Cs), and an alkaline earth metal such as magnesium (Mg), calcium (Ca), and strontium (Sr), and an alloy containing the same (e.g., MgAg, AlLi), a rare earth metal such as europium (Eu) and ytterbium (Yb), and an alloy containing the same can be given.

[1678] Note that in the case of forming a cathode using an alkali metal, an alkaline earth metal, and an alloy containing the same, a vacuum evaporation method, a sputtering method, or the like can be used. In the case of using silver paste or the like, a coating method, an inkjet method, or the like can be used.

[1679] Note that by providing the electron injection layer, a cathode can be formed using Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, and the like, which are various conductive materials, regardless of the size of the work function. These conductive materials can be deposited by a sputtering method, an inkjet method, a spin coating method, or the like.

[1680] Insulating layer

[1681] An organic EL element is likely to have a pixel defect due to leakage or a short circuit because an electric field is applied to an ultra-thin film. In order to prevent such a situation, an insulating layer formed of an insulating thin film layer can be interposed between a pair of electrodes.

[1682] As a material that can be used for the insulating layer, for example, 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, vanadium oxide, and the like can be given. Note that a mixture or a laminate thereof can also be used.

[1683] Separation layer

[1684] In the case of stacking the fluorescent light emitting layer and the phosphorescent light emitting layer, for example, the separation layer is provided between the fluorescent light emitting layer and the phosphorescent light emitting layer for the purpose of not allowing the exciton generated in the phosphorescent light emitting layer to diffuse to the fluorescent light emitting layer or adjusting the carrier balance. In addition, the separation layer can be provided between a plurality of phosphorescent light emitting layers.

[1685] The separation layer is provided between the light emitting layers, and thus is preferably a material having both electron transportability and hole transportability. In addition, in order to prevent diffusion of the triplet energy in the adjacent phosphorescent light emitting layers, the triplet energy is preferably 2.6 eV or more. As a material for the separation layer, the same material as the material for the hole transport layer described above can be given.

[1686] Barrier layer

[1687] A barrier layer such as an electron barrier layer, a hole barrier layer, or an exciton barrier layer can be provided adjacent to the light emitting layer. The electron barrier layer is a layer that prevents electrons from leaking from the light emitting layer to the hole transport layer, and the hole barrier layer is a layer that prevents holes from leaking from the light emitting layer to the electron transport layer. The exciton barrier layer has a function of preventing the exciton generated in the light emitting layer from diffusing to the periphery and enclosing the exciton in the light emitting layer.

[1688] Each layer of the organic EL element described above can be formed by a publicly known evaporation method, a coating method, or the like. For example, a publicly known method based on an evaporation method such as a vacuum evaporation method, a molecular beam evaporation method (MBE method), or the like, or a coating method such as a dip coating method, a spin coating method, a flow casting method, a bar coating method, a roll coating method, or the like using a solution of a compound that forms the layer can be used.

[1689] The film thickness of each layer is not particularly limited, and in general, if the film thickness is too thin, defects such as pinholes are easily generated, and on the contrary, if the film thickness is too thick, a high driving voltage is required, and the efficiency deteriorates, and thus the film thickness is usually 5 nm to 10 μm, and more preferably 10 nm to 0.2 μm.

[1690] In the organic EL element having the 2-layer structure or the 3-layer structure of the hole transport layer of the present application, the total thickness of the thickness of the first hole transport layer and the thickness of the second hole transport layer is preferably 30 nm or more and 150 nm or less, and more preferably 40 nm or more and 130 nm or less.

[1691] In one embodiment of the present invention, the thickness of the second hole transport layer of the two-layer or three-layer structure is preferably 5 nm or more, more preferably 20 nm or more, further preferably 25 nm or more, particularly preferably 35 nm or more, and preferably 100 nm or less.

[1692] In one embodiment of the present invention, the thickness of the hole transport layer adjacent to the light-emitting layer is preferably 5 nm or more, more preferably 20 nm or more, further preferably 25 nm or more, particularly preferably 30 nm or more, and preferably 100 nm or less.

[1693] In the organic EL device having a two-layer or three-layer hole transport layer of the present invention, the ratio of the thickness D2 of the second hole transport layer to the thickness D1 of the first hole transport layer is preferably 0.3. <D2 / D1<4.0、更优选为0.5<D2 / D1<3.5、进一步优选为0.75<D2 / D1<3.0。

[1694] Preferred embodiments of the organic EL device of the present invention include, for example:

[1695] (1) Organic EL element with a two-layer hole transport layer

[1696] The first embodiment in which the second hole-transporting layer contains the inventive compound and the first hole-transporting layer does not contain the inventive compound;

[1697] The second embodiment wherein both the first hole transport layer and the second hole transport layer comprise the inventive compound;

[1698] A third embodiment in which the first hole-transporting layer comprises the inventive compound and the second hole-transporting layer does not comprise the inventive compound;

[1699] (2) Organic EL element with a three-layer hole transport layer

[1700] A fourth embodiment in which the first hole-transporting layer comprises the inventive compound, and the second and third hole-transporting layers do not comprise the inventive compound;

[1701] A fifth embodiment in which the second hole-transporting layer comprises the inventive compound, and the first and third hole-transporting layers do not comprise the inventive compound;

[1702] A sixth embodiment in which the third hole-transporting layer comprises the inventive compound, and the first and second hole-transporting layers do not comprise the inventive compound;

[1703] A seventh embodiment in which the first hole-transporting layer and the second hole-transporting layer contain the compound of the invention, and the third hole-transporting layer does not contain the compound of the invention;

[1704] An eighth embodiment in which the first hole-transporting layer and the third hole-transporting layer contain the compound of the invention, and the second hole-transporting layer does not contain the compound of the invention;

[1705] A ninth embodiment in which the second hole-transporting layer and the third hole-transporting layer contain the compound of the invention, and the first hole-transporting layer does not contain the compound of the invention;

[1706] The tenth embodiment wherein the first to third hole-transporting layers all comprise the inventive compound; and so on.

[1707] electronic devices

[1708] An organic EL element according to one embodiment of the present invention can be used in electronic devices such as display devices and light-emitting devices. Examples of display devices include display components such as organic EL panel modules, televisions, mobile phones, tablet computers, and personal computers. Examples of light-emitting devices include lighting fixtures and vehicle lamps.

[1709] The organic EL element can be used in display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and electronic devices such as lighting and light-emitting devices for vehicle lamps.

[1710] Example

[1711] Hereinafter, the present invention will be described in further detail using examples, but the present invention is not limited to the following examples.

[1712] Invention compounds used in the production of organic EL devices (I) of Examples 1 to 5

[1713] [Chemical Formula 376]

[1714]

[1715] Comparative compound used in the production of the organic EL device (I) of Comparative Example 1

[1716] [Chemical Formula 377]

[1717]

[1718] Other compounds used in the production of the organic EL devices (I) of Examples 1 to 5 and Comparative Example 1

[1719] [Chemical formula 378]

[1720]

[1721] Fabrication of organic EL elements (I)

[1722] Example 1

[1723] After the 25 mm x 75 mm x 1.1 mm glass substrate with ITO transparent electrode (anode) (Geomatec Co., Ltd.) was subjected to ultrasonic cleaning in isopropanol for 5 minutes, it was subjected to UV ozone cleaning for 30 minutes. The film thickness of the ITO was 130 nm.

[1724] The cleaned glass substrate with ITO transparent electrode was installed in the substrate holder of a vacuum deposition apparatus, and first, compound HT-1A and compound HA were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer having a film thickness of 10 nm. The mass ratio of compound HT-1A to compound HA (HT-1A:HA) was 97:3.

[1725] Next, compound HT-1A was deposited on the hole injection layer, thereby forming a first hole transport layer having a film thickness of 80 nm.

[1726] Next, compound Inv-1 was deposited on the first hole transport layer, thereby forming a second hole transport layer having a film thickness of 10 nm.

[1727] Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited on the second hole transport layer, thereby forming a light-emitting layer having a film thickness of 25 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 96:4.

[1728] Next, compound ET-1 was deposited on the light-emitting layer, thereby forming a first electron transport layer having a film thickness of 5 nm.

[1729] Next, compound ET-2 and Liq were co-deposited on the first electron transport layer, thereby forming a second electron transport layer having a film thickness of 20 nm. The mass ratio of compound ET-2 to Liq (ET-2:Liq) was 50:50.

[1730] Next, LiF was deposited on the second electron transport layer, thereby forming an electron injection electrode having a film thickness of 1 nm.

[1731] Then, metal Al was deposited on the electron injection electrode, thereby forming a metal cathode having a film thickness of 50 nm.

[1732] The layer constitution of the organic EL element (I) obtained by the above operation is shown below.

[1733] ITO (130) / HT-1A:HA = 97:3 (10) / HT-1A (80) / compound Inv-1 (10) / BH-1:BD-1 = 96:4 (25) / ET-1 (5) / ET-2:Liq = 50:50 (20) / LiF (1) / Al (50)

[1734] In the above layer constitution, the numbers in parentheses are film thicknesses (nm), and the ratio is a mass ratio.

[1735] Examples 2 to 5 and Comparative Example 1

[1736] As the second hole-transporting layer material, the compound described in Table 1 was used instead of the compound Inv-1, and otherwise, the same operation as in Example 1 was performed to produce an organic EL element (I).

[1737] Measurement of external quantum efficiency (EQE)

[1738] The obtained organic EL element (I) was measured at room temperature at a current density of 10 mA / cm 2 DC constant current driving was performed. The luminance was measured using a luminance meter (spectral luminance emission meter CS-1000 manufactured by Minolta Co.), and the external quantum efficiency (%) was calculated from the results. The results are shown in Table 1.

[1739] [Table 1]

[1740] Table 1

[1741]

[1742] From the results in Table 1, it is clear that the organic EL element (I) containing the inventive compound (compound Inv-1, compound Inv-3, compound Inv-4, compound Inv-6, and compound Inv-8) has a higher external quantum efficiency than the organic EL element containing the comparative compound Ref-1.

[1743] Inventive compounds used in the production of the organic EL element (II) of Examples 6 to 9

[1744] [Chemical Formula 379]

[1745]

[1746] Comparative compounds used in the production of the organic EL element (II) of Comparative Example 2

[1747] [Chemical Formula 380]

[1748]

[1749] Other compounds used in the production of the organic EL element (II) of Examples 6 to 9 and Comparative Example 2

[1750] [Chemical Formula 381]

[1751]

[1752] Fabrication of Organic EL Element (II)

[1753] Example 6

[1754] After a 25 mm x 75 mm x 1.1 mm glass substrate with ITO transparent electrode (anode) (manufactured by Geomatec Corporation) was subjected to ultrasonic cleaning in isopropanol for 5 minutes, it was subjected to UV ozone cleaning for 30 minutes. The film thickness of the ITO was 130 nm.

[1755] The cleaned glass substrate with ITO transparent electrode was mounted on a substrate holder of a vacuum deposition apparatus, and first, compound HT-1B and compound HA were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer having a film thickness of 10 nm. The mass ratio of compound HT-1A to compound HA (HT-1B:HA) was 97:3.

[1756] Next, compound HT-1B was deposited on the hole injection layer, thereby forming a first hole transport layer having a film thickness of 80 nm.

[1757] Next, compound Inv-2 was deposited on the first hole transport layer, thereby forming a second hole transport layer having a film thickness of 10 nm.

[1758] Next, compound BH-2 (host material) and compound BD-1 (dopant material) were co-deposited on the second hole transport layer, thereby forming a light-emitting layer having a film thickness of 25 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 96:4.

[1759] Next, compound ET-3 was deposited on the light-emitting layer, thereby forming a first electron transport layer having a film thickness of 10 nm.

[1760] Next, compound ET-4 was deposited on the first electron transport layer, thereby forming a second electron transport layer having a film thickness of 15 nm.

[1761] Next, LiF was deposited on the second electron transport layer, thereby forming an electron injection electrode having a film thickness of 1 nm.

[1762] Then, metal Al was deposited on the electron injection electrode, thereby forming a metal cathode having a film thickness of 50 nm.

[1763] The layer constitution of the organic EL element (II) obtained by the above operation is shown below.

[1764] ITO (130) / HT-1B: HA = 97:3 (10) / HT-1B (80) / compound Inv-2 (10) / BH-2: BD-1 = 96:4 (25) / ET-3 (10) / ET-4 (15) / LiF (1) / Al (50)

[1765] In the above layer constitution, the numbers in parentheses are film thicknesses (nm), and the ratios are mass ratios.

[1766] Examples 7 to 9 and Comparative Example 2

[1767] As the second hole-transporting layer material, the compound described in Table 2 was used instead of compound Inv-2, and otherwise, the operation was performed similarly to Example 6 to produce an organic EL element.

[1768] Measurement of element lifetime (LT95)

[1769] The obtained organic EL element (II) was subjected to current density of 50 mA / cm 2 A direct current was applied, and the time until the luminance decreased to 95% of the initial luminance was measured as the 95% lifetime (LT95). The results are shown in Table 2.

[1770] [Table 2]

[1771] Table 2

[1772]

[1773] As is clear from the results in Table 2, the organic EL element (II) containing the inventive compound (compound Inv-2, compound Inv-5, compound Inv-7, and compound Inv-9) has a longer lifetime than the organic EL element containing the comparative compound Ref-2.

[1774] Inventive compounds synthesized in synthesis examples

[1775] [Chemical Formula 382]

[1776]

[1777] Synthesis Example 1 of Intermediate: Synthesis of Intermediate A

[1778] [Chemical Formula 383]

[1779]

[1780] A mixture of 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzo[b]naphtho[2,l- d]furan 11.0 g (30.0 mmol), 3-chloroiodobenzene 4.09 mL (33.0 mmol), tetrakis(triphenylphosphine)palladium(0) 1.04 g (0.90 mmol), 2M aqueous sodium carbonate 37.5 mL (75.0 mmol), DME 100 mL was subjected to boiling point reflux for 7 hours under argon atmosphere. The reaction was cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 7.79 g of intermediate A as a white solid. Yield 79%.

[1781] Intermediate Synthesis Example 2: Synthesis of intermediate B

[1782] [Chemical Formula 384]

[1783]

[1784] In intermediate synthesis example 1, instead of 3-chloroiodobenzene, 4-chloroiodobenzene was used, and the same operation was performed, to give intermediate B as a white solid.

[1785] Intermediate Synthesis Example 3: Synthesis of intermediate C

[1786] [Chemical Formula 385]

[1787]

[1788] In intermediate synthesis example 1, instead of 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)benzo[b]naphtho[2,l-d]furan, 6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzo[b] naphtho[2,l-d]furan was used, and the same operation was performed, to give intermediate C as a white solid.

[1789] Intermediate Synthesis Example 4: Synthesis of intermediate D

[1790] [Chemical Formula 386]

[1791]

[1792] A mixture of intermediate A 3.45 g (10.5 mmol), 4-(1-naphthyl)-N-[4-(1-naphthyl) phenyl) aniline 4.22 g (10.0 mmol), tris(dibenzylideneacetone)dipalladium(0) 0.366 g, (0.400 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos) 0.328 g (0.800 mmol), sodium tert-butoxide 1.44 g (15.0 mmol), xylene 67 mL was subjected to boiling point reflux at 120°C for 7 hours under argon atmosphere. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 4.28 g of a white solid. Yield was 60%.

[1793] Next, in the same manner as in Intermediate Synthesis Example 1, except that intermediate D-1 was used instead of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]naphtho[2,1-d]furan, 1-bromo-4-iodobenzene-d4 was used instead of 3-chloroiodobenzene, intermediate D was obtained as a white solid.

[1794] Intermediate Synthesis Example 5: Synthesis of intermediate E

[1795] [Chemical Formula 387]

[1796]

[1797] In the same manner as in Intermediate Synthesis Example 4, except that intermediate B was used instead of intermediate A, intermediate E was obtained as a white solid.

[1798] Synthesis Example 1: Synthesis of compound Inv-1

[1799] [Chemical Formula 388]

[1800]

[1801] A mixture of intermediate A 3.45 g (10.5 mmol), 4-(1-naphthyl)-N-[4-(1-naphthyl) phenyl) aniline 4.22 g (10.0 mmol), tris(dibenzylideneacetone)dipalladium(0) 0.366 g, (0.400 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos) 0.328 g (0.800 mmol), sodium tert-butoxide 1.44 g (15.0 mmol), xylene 67 mL was subjected to boiling point reflux at 120°C for 7 hours under argon atmosphere. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 4.28 g of a white solid. Yield was 60%.

[1802] The resulting substance was analyzed by mass spectrometry and was found to be compound Inv-1, m / e = 714 with respect to a molecular weight of 713.88.

[1803] Synthesis Example 2: Synthesis of compound Inv-2

[1804] [Chemical Formula 389]

[1805]

[1806] In Synthesis Example 1, instead of intermediate A, 6-(4-chlorophenyl)benzo[b]naphtho[2,l- d]furan was used, instead of 4-(l-naphthyl)-N-[4-(l-naphthyl)phenyl]aniline, N-[l,l'- biphenyl]-4-yl-[l,l'-biphenyl]-4-amine was used, and the same operation was performed, except for this, to obtain a white solid.

[1807] The resulting substance was analyzed by mass spectrometry and was found to be compound Inv-2, m / e = 614 with respect to a molecular weight of 613.76.

[1808] Synthesis Example 3: Synthesis of compound Inv-3

[1809] [Chemical Formula 390]

[1810]

[1811] In Synthesis Example 1, instead of 4-(l-naphthyl)-N-[4-(l-naphthyl)phenyl)aniline, di([l,l'-biphenyl]-4-yl)amine was used, and the same operation was performed, except for this, to obtain a white solid.

[1812] The resulting substance was analyzed by mass spectrometry and was found to be compound Inv-3, m / e = 614 with respect to a molecular weight of 613.76.

[1813] Synthesis Example 4: Synthesis of compound Inv-4

[1814] [Chemical Formula 391]

[1815]

[1816] In Synthesis Example 3, instead of intermediate A, intermediate B was used, and the same operation was performed, except for this, to obtain a white solid.

[1817] The resulting substance was analyzed by mass spectrometry and was found to be compound Inv-4, m / e = 614 with respect to a molecular weight of 613.76.

[1818] Synthesis Example 5: Synthesis of compound Inv-5

[1819] [Chemical Formula 392]

[1820]

[1821] In Synthesis Example 1, instead of intermediate A, intermediate C was used, and the same operation was performed except for this, to obtain a white solid.

[1822] The obtained substance was subjected to mass spectrometric analysis, and as a result, it was compound Inv-5, m / e = 614 with respect to the molecular weight of 613.76.

[1823] Synthesis Example 6: Synthesis of compound Inv-6

[1824] [Chemical Formula 393]

[1825]

[1826] In Synthesis Example 1, instead of intermediate A, intermediate D was used, and instead of 4-(1-naphthyl)-N-[4-(1-naphthyl)phenyl] aniline, intermediate F was used, and the same operation was performed except for this, to obtain a white solid.

[1827] The obtained substance was subjected to mass spectrometric analysis, and as a result, it was compound Inv-6, m / e = 712 with respect to the molecular weight of 711.99.

[1828] Synthesis Example 7: Synthesis of compound Inv-7

[1829] [Chemical Formula 394]

[1830]

[1831] In Synthesis Example 1, instead of intermediate A, intermediate E was used, and instead of 4-(1-naphthyl)-N-[4-(1-naphthyl)phenyl] aniline, intermediate F was used, and the same operation was performed except for this, to obtain a white solid.

[1832] The obtained substance was subjected to mass spectrometric analysis, and as a result, it was compound Inv-7, m / e = 712 with respect to the molecular weight of 711.99.

[1833] Synthesis Example 8: Synthesis of compound Inv-8

[1834] [Chemical Formula 395]

[1835]

[1836] In Synthesis Example 1, instead of intermediate A, intermediate B was used, and instead of 4-(1-naphthyl)-N-[4-(1-naphthyl)phenyl] aniline, intermediate G was used, and the same operation was performed except for this, to obtain a white solid.

[1837] The resulting substance was analyzed by mass spectrometry, and was found to be compound Inv-8, m / e = 712 with respect to a molecular weight of 711.89.

[1838] Synthesis Example 9: Synthesis of compound Inv-9

[1839] [Chemical Formula 396]

[1840]

[1841] In Synthesis Example 1, the same operation was performed except that 6-(4- chlorophenyl)benzo[b]naphtho[2,l-d]furan was used instead of intermediate A, and intermediate H was used instead of 4-(l-naphthyl)-N-[4-(l-naphthyl)phenyl]aniline, to obtain a white solid.

[1842] The resulting substance was analyzed by mass spectrometry, and was found to be compound Inv-9, m / e = 597 with respect to a molecular weight of 596.78.

[1843] Explanation of symbols

[1844] 1, 11, 12 Organic EL element

[1845] 2 Substrate

[1846] 3 Anode

[1847] 4 Cathode

[1848] 5 Light-emitting layer

[1849] 6 Hole-transporting region (hole-transporting layer)

[1850] 6a Hole-injecting layer

[1851] 6b First hole-transporting layer

[1852] 6c Second hole-transporting layer

[1853] 6d Third hole-transporting layer

[1854] 7 Electron-transporting region (electron-transporting layer)

[1855] 7a First electron-transporting layer

[1856] 7b Second electron-transporting layer

[1857] 10, 20, 30 Light-emitting unit

Claims

1. A compound represented by the following formula (A), wherein In formula (A), N * is the central nitrogen atom, k is 0 or 1, When k is 0, select R a1 ~R a6 One of them is a single bond to *x, When k is 1, R a1 With R a2 、R a2 With R a3 、R a3 With R a4 、R a5 With R a6 、R a7 With R a8 or R a9 With R a10 One of them is a single bond bonded to *a, and the other is a single bond bonded to *b, In the selection of R a1 With R a2 、R a2 With R a3 、R a3 With R a4 , and R a5 With R a6 When one of the groups is a single bond bonded to *a and the other is a single bond bonded to *b, R is selected from the group that is not a single bond bonded to *a and *b. a1 ~R a6 , and R a11 ~R a14 One of them is a single bond to *x, In the selection of R a7 With R a8 , and R a9 With R a10 When one of the groups is a single bond bonded to *a and the other is a single bond bonded to *b, R a1 ~R a6 One of them is a single bond to *x, R is not a single bond to *x and is not a single bond to *a and *b a1 ~R a10 , and R that is not a single bond to *x a11 ~R a14 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a halogen atom, R selected from a single bond other than that bonded to *x a11 ~R a14 The two adjacent ones in are not bonded to each other and thus do not form a ring. R a1 ~R a24 is a hydrogen atom, X a1 is an oxygen atom or a sulfur atom, L a1 ~L a4 are each independently a single bond or represented by the following formulas (i) to (iii), Selected from R 1 ~R 5 One of them is a single bond to *2, Selected from R 11 ~R 15 One of them is a single bond to *5, selected from R 16 ~R 20 The other one in is a single bond bonded to *6, Selected from R 21 ~R 28 One of them is a single bond bonded to *9, selected from R 21 ~R 28 The other one in is a single bond bonded to *10, R other than the single bond 1 ~R 5 , R other than the single bond 11 ~R 20 , and R other than the single bond 21 ~R 28 Each of them is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 )、-O-(R 904 )、-S-(R 905 ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms, R 901 ~R 905 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In R 901 If there are two or more, two or more R 901 Same or different from each other, In R 902 If there are two or more, two or more R 902 Same or different from each other, In R 903 If there are two or more, two or more R 903 Same or different from each other, In R 904 If there are two or more, two or more R 904 Same or different from each other, In R 905 If there are two or more, two or more R 905 Same or different from each other, *1, *4, and *8 represent the bonding position to the central nitrogen atom N*, or *x, *3, *7, and *11 indicate the same as Ar a1 、Ar a2 or the bonding position of benzene ring A, R selected from other than said single bond 1 ~R 5 , R other than the single bond 11 ~R 20 , and R other than the single bond 21 ~R 28 Two adjacent ones of the group are optionally bonded to each other to form a substituted or unsubstituted ring structure, or are not bonded to each other to form no ring, Ar a1 and Ar a2 are each independently represented by the following formulas (a) to (f), In formula (a), *21 is with L a1 or L a2 The bonding position of Selected from R 101 ~R 105 One of them is a single bond to *22, selected from R 106 ~R 110 One of them is a single bond to *23, R other than the single bond 101 ~R 105 , and R 106 ~R 110 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms, R selected from other than said single bond 101 ~R 105 The two adjacent ones in are not bonded to each other and do not form a ring. R selected from other than said single bond 106 ~R 110 The two adjacent ones in are not bonded to each other and do not form a ring. R 111 ~R 115 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms, Selected from R 111 ~R 115 The two adjacent ones in are not bonded to each other and do not form a ring. m is 0, 1 or 2, n is 0 or 1, In the case of m=0, n=0, *23 means *21, In the case of m=0, n=1, *22 means *21, In the case of m=1 and n=0, *23 means *22. Among them, when k is 0, R a5 is a single bond bonded to *x, L a1 、L a3 and L a4 When Ar is a single bond, a1 In the formula (a) represented by: m+n is 0, 1 or 3, When k is 0, R a5 is a single bond bonded to *x, L a3 and L a4 For a single bond, L a1 In the case represented by formula (i), Ar a1 In the formula (a), m+n is 0, 2 or 3, When k is 0, R a5 is a single bond bonded to *x, L a3 and L a4 For a single bond, L a1 In the case represented by formula (i), Ar a1 In the formula (a), m+n is 1, 2 or 3, In formula (b), *24 is with L a1 or L a2 The bonding position of Selected from R 121 ~R 128 One of them is a single bond to *25, R other than the single bond 121 ~R 128 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, R selected from other than said single bond 121 ~R 128 The two adjacent ones in are not bonded to each other and do not form a ring. In formula (c), *26 is with L a1 or L a2 The bonding position of Selected from R 131 ~R 140 One of them is a single bond to *27, R other than the single bond 131 ~R 140 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, R selected from other than said single bond 131 ~R 140 The two adjacent ones in are not bonded to each other and do not form a ring. Among them, in R a5 is a single bond bonded to *x, L a1 ~L a4 In the case of a single bond, R 131 、R 132 、R 134 、R 135 and R 137 ~R 140 One of them is a single bond to *27, In formula (d), *28 is with L a1 or L a2 The bonding position of X 11 For oxygen atoms, sulfur atoms, CR A R B or NR C , R A and R B are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and R A and R B are optionally bonded to each other to form a substituted or unsubstituted ring structure, or are not bonded to each other to form no ring, R C is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, l is 0 or 1, When l is 0, select R A 、R B 、R C and R 141 ~R 148 One of them is a single bond to *29, or R A or R B A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, R A or R B may be bonded to form a substituted or unsubstituted ring structure or R C The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms is bonded to *29 via a single bond. When l is 1, R 141 With R 142 、R 142 With R 143 , or R 143 With R 144 One of them is a single bond bonded to *c, and the other is a single bond bonded to *d, R selected from single bonds other than those bonded to *c and *d 141 ~R 144 、R 145 ~R 148 、R A 、R B 、R C , and R 200 ~R 203 One of them is a single bond to *29, or R A or R B It may represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or R A or R B may be bonded to each other to form a substituted or unsubstituted ring structure, or R C The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms is bonded to *29 via a single bond. R other than the single bond 141 ~R 148 , and R other than the single bond 200 ~R 203 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms, R selected from other than said single bond 141 ~R 148 , and R other than the single bond 200 ~R 203 The two adjacent ones in are not bonded to each other and do not form a ring. In formula (e), *30 is with L a1 or L a2 The bonding position of Selected from R 151 ~R 155 One of them is a single bond to *31, selected from R 151 ~R 155 The other one in is a single bond bonded to *32, R other than the single bond 151 ~R 155 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group, R selected from other than said single bond 151 ~R 155 The two adjacent ones in are not bonded to each other and do not form a ring. R 161 ~R 165 and R 171 ~R 175 are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms, Selected from R 161 ~R 165 At least one pair of adjacent two of the alkyl groups are optionally bonded to each other to form one or more unsubstituted benzene rings, or are not bonded to each other to form no ring, Selected from R 171 ~R 175 At least one pair of adjacent two of the alkyl groups are optionally bonded to each other to form one or more unsubstituted benzene rings, or are not bonded to each other to form no ring, In formula (f), *32 is the same as L a1 or L a2 The bonding position of Selected from R 181 ~R 192 One of them is a single bond to *33, R other than the single bond 181 ~R 192 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, R selected from other than said single bond 181 ~R 192 The two adjacent ones in are not bonded to each other and do not form a ring. Among them, in L a1 and L a2 Phenylene, L a3 and L a4 is a single bond, Ar a1 and Ar a2 In the case of the above formula (b), L a1 It is 1,2-phenylene or 1,4-phenylene.

2. The compound according to claim 1, wherein L a3 is a single bond or is represented by the above formula (i).

3. The compound according to claim 1 or 2, wherein L a3 For a single bond.

4. The compound according to any one of claims 1 to 3, wherein L a4 is a single bond or is represented by the above formula (i).

5. The compound according to any one of claims 1 to 4, wherein L a4 For a single bond.

6. The compound according to any one of claims 1 to 5, wherein Ar a1 It is represented by the formula (a), (b) or (c).

7. The compound according to any one of claims 1 to 6, wherein Ar a1 It is represented by the above formula (b).

8. The compound according to any one of claims 1 to 7, wherein Ar a2 It is represented by the formula (a), (b) or (c).

9. The compound according to any one of claims 1 to 8, wherein Ar a2 It is represented by the above formula (b).

10. The compound according to any one of claims 1 to 5, wherein Ar a1 It is represented by the above formula (d).

11. The compound according to any one of claims 1 to 7 and 10, wherein Ar a2 It is represented by the above formula (d).

12. The compound according to any one of claims 1 to 11, wherein The compound represented by formula (A) contains at least one deuterium atom.

13. A compound represented by the following formula (B) and containing at least one deuterium atom, wherein: In formula (B), N * is the central nitrogen atom, p is 0 or 1, When p is 0, R b4 or R b6 is a single bond bonded to *y, When p is 1, R b1 With R b2 、R b2 With R b3 、R b3 With R b4 、R b5 With R b6 、R b7 With R b8 、R b8 With R b9 , or R b9 With R b10 One of them is a single bond bonded to *e, and the other is a single bond bonded to *f, In R b3 With R b4 When one of them is a single bond bonded to *e and the other is a single bond bonded to *f, R b6 is a single bond bonded to *y, In R b5 With R b6 When one of them is a single bond bonded to *e and the other is a single bond bonded to *f, R b4 is a single bond bonded to *y, In R b3 With R b4 One of them is not a single bond to *e, the other is not a single bond to *f, and R b5 With R b6 When one of them is not a single bond to *e and the other is not a single bond to *f, R b4 or R b6 is a single bond bonded to *y, R is not a single bond to *y and is not a single bond to *e and *f b1 ~R b10 , and R that is not a single bond to *y b11 ~R b14 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a halogen atom, R selected from a single bond other than a bond to *y b11 ~R b14 The two adjacent ones in are not bonded to each other and thus do not form a ring. R b21 ~R b24 is a hydrogen atom, X b1 is an oxygen atom or a sulfur atom, L b1 ~L b4 are each independently a single bond or represented by the following formulas (i) to (iii), Selected from R 1 ~R 5 One of them is a single bond to *2, Selected from R 11 ~R 15 One of them is a single bond to *5, selected from R 16 ~R 20 The other one in is a single bond bonded to *6, Selected from R 21 ~R 28 One of them is a single bond bonded to *9, selected from R 21 ~R 28 The other one in is a single bond bonded to *10, R other than the single bond 1 ~R 5 , R other than the single bond 11 ~R 20 , and R other than the single bond 21 ~R 28 Each of them is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 )、-O-(R 904 )、-S-(R 905 ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms, R 901 ~R 905 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In R 901 If there are two or more, two or more R 901 Same or different from each other, In R 902 If there are two or more, two or more R 902 Same or different from each other, In R 903 If there are two or more, two or more R 903 Same or different from each other, In R 904 If there are two or more, two or more R 904 Same or different from each other, In R 905 If there are two or more, two or more R 905 Same or different from each other, *1, *4, and *8 represent the central nitrogen atom N * The bonding position, or *y, *3, *7, and *11 indicate the same as Ar b1 、Ar b2 or the bonding position of benzene ring B, R selected from other than said single bond 1 ~R 5 , R other than the single bond 11 ~R 20 , and R other than the single bond 21 ~R 28 Two adjacent ones of the group are optionally bonded to each other to form a substituted or unsubstituted ring structure, or are not bonded to each other to form no ring, Ar b1 and Ar b2 are each independently represented by the following formulas (a) to (f), In formula (a), *21 is with L b1 or L b2 The bonding position of Selected from R 101 ~R 105 One of them is a single bond to *22, selected from R 106 ~R 110 One of them is a single bond to *23, R other than the single bond 101 ~R 105 , and R 106 ~R 110 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms, R selected from other than said single bond 101 ~R 105 The two adjacent ones in are not bonded to each other and do not form a ring. R selected from other than said single bond 106 ~R 110 The two adjacent ones in are not bonded to each other and do not form a ring. R 111 ~R 115 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms, Selected from R 111 ~R 115 The two adjacent ones in are not bonded to each other and do not form a ring. m is 0, 1 or 2, n is 0 or 1, In the case of m=0, n=0, *23 means *21, In the case of m=0, n=1, *22 means *21, In the case of m=1 and n=0, *23 means *22. In formula (b), *24 is with L b1 or L b2 The bonding position of Selected from R 121 ~R 128 One of them is a single bond to *25, R other than the single bond 121 ~R 128 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, R selected from other than said single bond 121 ~R 128 The two adjacent ones in are not bonded to each other and do not form a ring. In formula (c), *26 is with L b1 or L b2 The bonding position of Selected from R 131 ~R 140 One of them is a single bond to *27, R other than the single bond 131 ~R 140 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, R selected from other than said single bond 131 ~R 140 The two adjacent ones in are not bonded to each other and do not form a ring. In formula (d), *28 is with L b1 or L b2 The bonding position of X 11 For oxygen atoms, sulfur atoms, CR A R B or NR C , R A and RB are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and R A and R B are optionally bonded to each other to form a substituted or unsubstituted ring structure, or are not bonded to each other to form no ring, R C is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, l is 0 or 1, When 1 is 0, select R A 、R B 、R C , and R 141 ~R 148 One of them is a single bond to *29, or R A or R B A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, R A or R B may be bonded to each other to form a substituted or unsubstituted ring structure, or R C The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms is bonded to *29 via a single bond. When l is 1, R 141 With R 142 、R 142 With R 143 , or R 143 With R 144 One of them is a single bond bonded to *c, and the other is a single bond bonded to *d, R selected from single bonds other than those bonded to *c and *d 141 ~R 144 、R 145 ~R 148 、R A 、R B 、R C , and R 200 ~R 203 One of them is a single bond to *29, or R A or R B It may represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or R A or R B may be bonded to each other to form a substituted or unsubstituted ring structure, or R C The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms is bonded to *29 via a single bond. Among them, in L b1 、L b3 and L b4 is a single bond, l is 0, X 11 CR A R B In the case of R 141 ~R 148 One of them is a single bond to *29, R other than the single bond 141 ~R 148 , and R2 which is not a single bond 00 ~R 203 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms, R selected from other than said single bond 141 ~R 148 , and R other than the single bond 200 ~R 203 The two adjacent ones in are not bonded to each other and do not form a ring. In formula (e), *30 is with L b1 or L b2 The bonding position of Selected from R 151 ~R 155 One of them is a single bond to *31, selected from R 151 ~R 155 The other one in is a single bond bonded to *32, R other than the single bond 151 ~R 155 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group, R selected from other than said single bond 151 ~R 155 The two adjacent ones in are not bonded to each other and do not form a ring. R 161 ~R 165 and R 171 ~R 175 are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms, Selected from R 161 ~R 165 At least one pair of adjacent two of the alkyl groups are optionally bonded to each other to form one or more unsubstituted benzene rings, or are not bonded to each other to form no ring, Selected from R 171 ~R 175 At least one pair of adjacent two of the alkyl groups are optionally bonded to each other to form one or more unsubstituted benzene rings, or are not bonded to each other to form no ring, In formula (f), *32 is the same as L b1 or L b2 The bonding position of Selected from R 181 ~R 192 One of them is a single bond to *33, R other than the single bond 181 ~R 192 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, R selected from other than said single bond 181 ~R 192 The two adjacent ones in are not bonded to each other and do not form a ring. Among them, in L b1 ~L b4 When Ar is a single bond, b1 Represented by formula (a) or (c) to (f), in Ar b1 In the case of formula (a), m+n is 1, 2 or 3.

14. The compound according to claim 13, wherein L b3 is a single bond or is represented by the above formula (i).

15. The compound according to claim 13 or 14, wherein L b3 For a single bond.

16. The compound according to any one of claims 13 to 15, wherein L b4 is a single bond, or is represented by the above formula (i).

17. The compound according to any one of claims 13 to 16, wherein L b4 It is represented by the above formula (i).

18. The compound according to any one of claims 13 to 17, wherein Ar b1 It is represented by the formula (a), (b) or (c).

19. The compound according to any one of claims 13 to 18, wherein Ar b1 It is represented by the above formula (a).

20. The compound according to any one of claims 13 to 19, wherein Ar b2 It is represented by the formula (a), (b) or (c).

21. The compound according to any one of claims 13 to 20, wherein Ar b2 It is represented by the above formula (a).

22. The compound according to any one of claims 13 to 17, wherein Ar b1 It is represented by the above formula (d).

23. The compound according to any one of claims 13 to 19 and 22, wherein Ar b2 It is represented by the above formula (d). 24 . A material for an organic electroluminescent device, comprising the compound according to claim 1 . 25 . An organic electroluminescent device comprising a cathode, an anode, and an organic layer located between the cathode and the anode, wherein the organic layer includes a light-emitting layer, and at least one layer of the organic layer includes the compound according to claim 1 .

26. An organic electroluminescent device comprising an anode, a light-emitting layer, and a cathode, an organic layer between the anode and the light-emitting layer, at least one layer of the organic layer comprising a compound represented by the following formula (B'): In formula (B'), N * is the central nitrogen atom, p is 0 or 1, When p is 0, R b4 or R b6 is a single bond bonded to *y, When p is 1, R b1 With R b2 、R b2 With R b3 、R b3 With R b4 、R b5 With R b6 、R b7 With R b8 、R b8 With R b9 , or R b9 With R b10 One of them is a single bond bonded to *e, and the other is a single bond bonded to *f, In R b3 With R b4 When one of them is a single bond bonded to *e and the other is a single bond bonded to *f, R b6 is a single bond bonded to *y, In R b5 With R b6 When one of them is a single bond bonded to *e and the other is a single bond bonded to *f, R b4 is a single bond bonded to *y, In R b3 With R b4 One of them is not a single bond to *e, the other is not a single bond to *f, and R b5 With R b6 When one of them is not a single bond to *e and the other is not a single bond to *f, R b4 or R b6 is a single bond bonded to *y, R is not a single bond to *y and is not a single bond to *e and *f b1 ~R b10 , and R that is not a single bond to *y b11 ~R b14 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a halogen atom, R selected from a single bond other than a bond to *y b11 ~R b14 The two adjacent ones in are not bonded to each other and thus do not form a ring. R b21 ~R b24 is a hydrogen atom, X b1 is an oxygen atom or a sulfur atom, L b1 ~Lb 4 are each independently a single bond or represented by the following formulas (i) to (iii), Selected from R 1 ~R 5 One of them is a single bond to *2, Selected from R 11 ~R 15 One of them is a single bond to *5, selected from R 16 ~R 20 The other one in is a single bond bonded to *6, Selected from R 21 ~R 28 One of them is a single bond bonded to *9, selected from R 21 ~R 28 The other one in is a single bond bonded to *10, R other than the single bond 1 ~R 5 , R other than the single bond 11 ~R 20 , and R other than the single bond 21 ~R 28 Each of them is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 )、-O-(R 904 )、-S-(R 905 ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms, R 901 ~R 905 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In R 901 If there are two or more, two or more R 901 Same or different from each other, In R 902 If there are two or more, two or more R 902 Same or different from each other, In R 903 If there are two or more, two or more R 903 Same or different from each other, In R 904 If there are two or more, two or more R 904 Same or different from each other, In R 905 If there are two or more, two or more R 905 Same or different from each other, *1, *4, and *8 represent the central nitrogen atom N * The bonding position, or *y, *3, *7, and *11 indicate the same as Ar b1 、Ar b2 or the bonding position of benzene ring B, R selected from other than said single bond 1 ~R 5 , R other than the single bond 11 ~R 20 , and R other than the single bond 21 ~R 28 Two adjacent ones of the group are optionally bonded to each other to form a substituted or unsubstituted ring structure, or are not bonded to each other to form no ring, Ar b1 and Ar b2 are each independently represented by the following formulas (a) to (f), In formula (a), *21 is the same as L b1 or L b2 The bonding position of Selected from R 101 ~R 105 One of them is a single bond to *22, selected from R 106 ~R 110 One of them is a single bond to *23, R other than the single bond 101 ~R 105 , and R 106 ~R 110 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms, R selected from other than said single bond 101 ~R 105 The two adjacent ones in are not bonded to each other and do not form a ring. R selected from other than said single bond 106 ~R 110 The two adjacent ones in are not bonded to each other and do not form a ring. R 111 ~R 115 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms, Selected from R 111 ~R 115 The two adjacent ones in are not bonded to each other and do not form a ring. m is 0, 1 or 2, n is 0 or 1, In the case of m=0, n=0, *23 means *21, In the case of m=0, n=1, *22 means *21, In the case of m=1 and n=0, *23 means *22. In formula (b), *24 is with L b1 or L b2 The bonding position of Selected from R 121 ~R 128 One of them is a single bond to *25, R other than the single bond 121 ~R 128 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, R selected from other than said single bond 121 ~R 128 The two adjacent ones in are not bonded to each other and do not form a ring. In formula (c), *26 is the same as L b1 or L b2 The bonding position of Selected from R 131 ~R 140 One of them is a single bond to *27, R other than the single bond 131 ~R 140 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, R selected from other than said single bond 131 ~R 140 The two adjacent ones in are not bonded to each other and do not form a ring. In formula (d), *28 is with L b1 or L b2 The bonding position of X 11 For oxygen atoms, sulfur atoms, CR A R B or NR C , R A and R B are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and R A and R B are optionally bonded to each other to form a substituted or unsubstituted ring structure, or are not bonded to each other to form no ring, R C is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, l is 0 or 1, When l is 0, select R A 、R B 、R C , and R 141 ~R 148 One of them is a single bond to *29, or R A or R B A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, R A or R B may be bonded to each other to form a substituted or unsubstituted ring structure, or R C The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms is bonded to *29 via a single bond. When l is 1, R 141 With R 142 、R 142 With R 143 , or R 143 With R 144 One of them is a single bond bonded to *c, and the other is a single bond bonded to *d, and R is selected from single bonds other than those bonded to *c and *d. 141 ~R 144 、R 145 ~R 148 、R A 、R B 、R C , and R2 00 ~R 203 One of them is a single bond to *29, or R A or R B It may represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or R A or R B may be bonded to each other to form a substituted or unsubstituted ring structure, or R C The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms is bonded to *29 via a single bond. in, In L b1 、L b3 and L b4 is a single bond, l is 0, X 11 CR A R B In the case of R 141 ~R 148 One of them is a single bond to *29, R other than the single bond 141 ~R 148 , and R other than the single bond 200 ~R 203 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms, R selected from other than said single bond 141 ~R 148 , and R other than the single bond 200 ~R 203 The two adjacent ones in are not bonded to each other and do not form a ring. In formula (e), *30 is with L b1 or L b2 The bonding position of Selected from R 151 ~R 155 One of them is a single bond to *31, selected from R 151 ~R 155 The other one in is a single bond bonded to *32, R other than the single bond 151 ~R 155 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group, R selected from other than said single bond 151 ~R 155 The two adjacent ones in are not bonded to each other and do not form a ring. R 161 ~R 165 and R 171 ~R 175 are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms, Selected from R16 1 ~R 165 At least one pair of adjacent two of the alkyl groups are optionally bonded to each other to form one or more unsubstituted benzene rings, or are not bonded to each other to form no ring, Selected from R 171 ~R 175 At least one pair of adjacent two of the alkyl groups are optionally bonded to each other to form one or more unsubstituted benzene rings, or are not bonded to each other to form no ring, In formula (f), *32 is the same as L b1 or L b2 The bonding position of Selected from R 181 ~R 192 One of them is a single bond to *33, R other than the single bond 181 ~R 192 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, R selected from other than said single bond 181 ~R 192 The two adjacent ones in are not bonded to each other and do not form a ring. Among them, in L b1 ~Lb 4 When Ar is a single bond, b1 Represented by formula (a) or (c) to (f), in Ar b1 In the case of formula (a), m+n is 1, 2 or 3.

27. The organic electroluminescent element according to claim 25 or 26, wherein The organic layer includes a hole transport region between the anode and the light emitting layer, and the hole transport region includes the compound.

28. The organic electroluminescent element according to claim 27, wherein The hole transport region includes a first hole transport layer on the anode side and a second hole transport layer on the cathode side, and one or both of the first hole transport layer and the second hole transport layer include the compound.

29. The organic electroluminescent element according to any one of claims 25 to 28, wherein The light-emitting layer includes a fluorescent dopant material.

30. The organic electroluminescent element according to any one of claims 25 to 28, wherein The light-emitting layer includes a phosphorescent dopant material. 31 . An electronic device comprising the organic electroluminescent element according to claim 25 .

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