Compounds, organic electroluminescence devices, and electronic devices
Patent Information
- Application Number
- KR1020227021537
- Authority / Receiving Office
- KR · KR
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2020-04-15
- Filing Date
- 2020-11-26
- Publication Date
- 2026-09-11
- Estimated Expiration
- 2040-11-26
Smart Images

Figure 112022065939493-PCT00450_ABST
Abstract
Description
Technology Field
[0001] The present invention relates to a compound, an organic electroluminescence device, and an electronic device. Background Technology
[0002] Organic electroluminescence devices (hereinafter referred to as "organic EL devices") are applied to full-color displays such as mobile phones and televisions. When voltage is applied to an organic EL device, holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. At this time, according to the statistical rule of electron spin, singlet excitons are generated at a rate of 25%, and triplet excitons are generated at a rate of 75%.
[0003] In order to improve the performance of organic EL devices, various studies have been conducted on compounds used in organic EL devices (e.g., see Patent Documents 1 to 6). Performance characteristics of organic EL devices include, for example, brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan. Prior art literature
[0004] Patent Document 1: Japanese Patent Publication No. 2013-157552 Patent Document 2: International Publication No. 2004 / 018587 Patent Document 3: International Publication No. 2005 / 115950 Patent Document 4: International Publication No. 2011 / 077691 Patent Document 5: Japanese Patent Publication No. 2018-125504 Patent Document 6: Specification of U.S. Patent Application Publication No. 2019 / 280209 The problem to be solved
[0005] One of the objectives of the present invention is to provide a compound capable of improving luminous efficiency, an organic EL device using the compound, and an electronic device equipped with the organic EL device.
[0006] One object of the present invention is to provide an organic electroluminescence device with improved performance. In addition, another object of the present invention is to provide an organic electroluminescence device with improved luminous efficiency, and to provide an electronic device equipped with said organic electroluminescence device. means of solving the problem
[0007] According to one aspect of the present invention, a compound represented by the following general formula (12X) is provided.
[0008] [Painting 1]
[0009]
[0010] (In the above general formula (12X),
[0011] Py1 and Py2 are each independently
[0012] It is a substituted or unsubstituted 1-pyrenyl group, and
[0013] L1 and L2 are each independently
[0014] A substituted or unsubstituted phenylene group, or
[0015] It is a substituted or unsubstituted naphthylene group, and
[0016] However, where L1 and L2 are each independently substituted or unsubstituted phenylene groups, -L1-L2- in the above general formula (12X) is a group represented by any one of the following general formulas (13-1) to (13-6), (10-1), (20-1) and (30-1), and where L1 and L2 are each independently substituted or unsubstituted naphthylene groups, the bonding position of the naphthylene group as L1 and the bonding position of the naphthylene group as L2 are different, and
[0017] When Py1 and Py2 are each independently a substituted 1-pyrenyl group, the substituent E of the said substituted 1-pyrenyl group is each independently
[0018] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0019] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms,
[0020] - A group represented as Si(Rx)(Ry)(Rz),
[0021] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0022] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0023] In Si(Rx)(Ry)(Rz), Rx, Ry, and Rz are each independently
[0024] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or
[0025] It is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[0026] When there are multiple substituents E, the multiple substituents E are either identical or different from each other.
[0027] (In the case of "substituent or non-substituent" regarding the above substituent E, the substituent F is each independently
[0028] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0029] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms,
[0030] Substituted or unsubstituted phenyl group,
[0031] Substituted or unsubstituted biphenyl group,
[0032] Substituted or unsubstituted terphenyl group,
[0033] Substituted or unsubstituted naphthyl group,
[0034] Substituted or unsubstituted anthryl group,
[0035] Substituted or unsubstituted phenanthryl group,
[0036] Substituted or unsubstituted crisenyl group,
[0037] Substituted or unsubstituted triphenylenyl group,
[0038] Substituted or unsubstituted fluorenyl group,
[0039] Substituted or unsubstituted 9,9'-spirobifluorenyl group,
[0040] Substituted or unsubstituted 9,9-dimethylfluorenyl group,
[0041] It is a substituted or unsubstituted 9,9-diphenylfluorenyl group.
[0042] [Painting 2]
[0043]
[0044] (In the above general formulas (13-1) to (13-6), R 11 ~R 15 and R 11A ~R 15A Each independently
[0045] hydrogen atom,
[0046] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0047] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms,
[0048] - A group represented as Si(Rx)(Ry)(Rz),
[0049] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0050] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0051] In Si(Rx)(Ry)(Rz), Rx, Ry, and Rz are each independently
[0052] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or
[0053] It is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[0054] R 11 ~R 15 In the case of "substituted or non-substituted," the substituents are each independently
[0055] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0056] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms,
[0057] Substituted or unsubstituted phenyl group,
[0058] Substituted or unsubstituted biphenyl group,
[0059] Substituted or unsubstituted terphenyl group,
[0060] Substituted or unsubstituted naphthyl group,
[0061] Substituted or unsubstituted anthryl group,
[0062] Substituted or unsubstituted phenanthryl group,
[0063] Substituted or unsubstituted crisenyl group,
[0064] Substituted or unsubstituted triphenylenyl group,
[0065] Substituted or unsubstituted fluorenyl group,
[0066] Substituted or unsubstituted 9,9'-spirobifluorenyl group,
[0067] A substituted or unsubstituted 9,9-dimethylfluorenyl group, or
[0068] It is a substituted or unsubstituted 9,9-diphenylfluorenyl group, and
[0069] R 11 ~R 15 Among them, one or more of the groups consisting of two or more adjacent groups do not combine with each other to form a single ring of substitution or non-substitution, and also do not form a condensed ring of substitution or non-substitution, and
[0070] R 11A ~R 15A Among them, one or more of the groups consisting of two or more adjacent groups do not combine with each other to form a single ring of substitution or non-substitution, and also do not form a condensed ring of substitution or non-substitution, and
[0071] In the above general formulas (13-1) to (13-6), *1 represents the bonding position with Py1 in the above general formula (12X), and *2 represents the bonding position with Py2 in the above general formula (12X).
[0072] [Tuesday 3]
[0073]
[0074] (In the above general formula (10-1), R 11 and R 12 of, R 13 and R 14 of, R 21 and R 22 of, R 23 and R 24 One or more of the groups consisting of the
[0075] They combine with each other to form a substituted or unsubstituted single ring,
[0076] They combine with each other to form substituted or unsubstituted condensed rings, or
[0077] Without combining with each other,
[0078] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 11 , R 13 , R 21 and R 23 Each independently
[0079] hydrogen atom,
[0080] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0081] Substituted or unsubstituted phenyl group,
[0082] Substituted or unsubstituted biphenyl group,
[0083] Substituted or unsubstituted naphthyl group,
[0084] Substituted or unsubstituted phenanthryl group,
[0085] Substituted or unsubstituted fluorenyl group,
[0086] A substituted or unsubstituted 9,9'-spirobifluorenyl group, or
[0087] It is represented by the following general formula (4), and
[0088] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 12 , R 14 , R 22 and R 24 Each independently
[0089] hydrogen atom,
[0090] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0091] Substituted or unsubstituted biphenyl group,
[0092] Substituted or unsubstituted naphthyl group,
[0093] Substituted or unsubstituted phenanthryl group,
[0094] Substituted or unsubstituted fluorenyl group,
[0095] A substituted or unsubstituted 9,9'-spirobifluorenyl group, or
[0096] It is represented by the following general formula (4), and
[0097] However, R 11 ~R 14 and R 21 ~R 24 At least one of them is not a hydrogen atom, and
[0098] In the above general formulas (20-1) and (30-1),
[0099] R 31 ~R 33 , R 41 ~R 43 , R 51 ~R 54 and R 61 ~R 64 One or more of the groups consisting of two or more adjacent groups
[0100] They combine with each other to form a substituted or unsubstituted single ring,
[0101] They combine with each other to form substituted or unsubstituted condensed rings, or
[0102] Without combining with each other,
[0103] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 and R 61 ~R 64 Each independently
[0104] hydrogen atom,
[0105] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0106] Substituted or unsubstituted phenyl group,
[0107] Substituted or unsubstituted biphenyl group,
[0108] Substituted or unsubstituted naphthyl group,
[0109] Substituted or unsubstituted phenanthryl group,
[0110] Substituted or unsubstituted fluorenyl group,
[0111] A substituted or unsubstituted spirobifluorenyl group, or
[0112] It is represented by the following general formula (4), and
[0113] However, R 31 ~R 34 and R 41 ~R 44 At least one of them is not a hydrogen atom, and
[0114] R 51 ~R 54 and R 61 ~R 64 At least one of them is not a hydrogen atom,
[0115] R in the compound represented by the above general formula (10-1). 11 and R13 The group of, and R 21 and R 23 The keys of are different keys, or R 12 and R 14 The group of, and R 22 and R 24 The groups are different from each other,
[0116] R in the compound represented by the above general formula (20-1) 31 and R 41 These are different from each other, or R 32 and R 42 are different from each other, or R 33 and R 43 These are different from each other, or R 34 and R 44 They are different from each other,
[0117] R in the compound represented by the above general formula (30-1) 51 and R 61 These are different from each other, or R 52 and R 62 are different from each other, or R 53 and R 63 These are different from each other, or R 54 and R 64 They are different from each other,
[0118] In the above general formulas (10-1), (20-1) and (30-1), *1 represents the bonding position with Py1 in the above general formula (12X), and *2 represents the bonding position with Py2 in the above general formula (12X).
[0119] [Painting 4]
[0120]
[0121] (In the above general formula (4), X 13 Silver oxygen atoms, sulfur atoms, or NR 319 is,
[0122] R 311 ~R 318 One or more of the groups consisting of two or more adjacent groups
[0123] They combine with each other to form a substituted or unsubstituted single ring,
[0124] They combine with each other to form substituted or unsubstituted condensed rings, or
[0125] Without combining with each other,
[0126] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 311 ~R 319 Each independently
[0127] hydrogen atom,
[0128] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0129] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms,
[0130] Substituted or unsubstituted phenyl group,
[0131] Substituted or unsubstituted biphenyl group,
[0132] Substituted or unsubstituted terphenyl group,
[0133] Substituted or unsubstituted naphthyl group,
[0134] Substituted or unsubstituted anthryl group,
[0135] Substituted or unsubstituted phenanthryl group,
[0136] Substituted or unsubstituted crisenyl group,
[0137] Substituted or unsubstituted triphenylenyl group,
[0138] Substituted or unsubstituted fluorenyl group,
[0139] Substituted or unsubstituted 9,9'-spirobifluorenyl group,
[0140] Substituted or unsubstituted 9,9-dimethylfluorenyl group,
[0141] It is a substituted or unsubstituted 9,9-diphenylfluorenyl group, and
[0142] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 311 ~R 319 One of them is R 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 and R 61 ~R 64 It is a single bond that bonds to at least one of them.)
[0143] (In the above general formulas (10-1), (20-1), (30-1) and the above general formula (4), R 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 , R 61 ~R 64 and R 311 ~R 319 In the case of "substituted or non-substituted," the substituents are each independently
[0144] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0145] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms,
[0146] Substituted or unsubstituted phenyl group,
[0147] Substituted or unsubstituted biphenyl group,
[0148] Substituted or unsubstituted terphenyl group,
[0149] Substituted or unsubstituted naphthyl group,
[0150] Substituted or unsubstituted anthryl group,
[0151] Substituted or unsubstituted phenanthryl group,
[0152] Substituted or unsubstituted crisenyl group,
[0153] Substituted or unsubstituted triphenylenyl group,
[0154] Substituted or unsubstituted fluorenyl group,
[0155] Substituted or unsubstituted 9,9'-spirobifluorenyl group,
[0156] Substituted or unsubstituted 9,9-dimethylfluorenyl group,
[0157] It is a substituted or unsubstituted 9,9-diphenylfluorenyl group.
[0158] According to one aspect of the present invention, a compound represented by the following general formula (120) is provided.
[0159] [Tuesday 5]
[0160]
[0161] (In the above general formula (120), L1 is represented by any one of the following general formulas (11) to (13), and L2 is represented by any one of the following general formulas (11A) to (13A).
[0162] R 102 ~R 119 Each independently
[0163] hydrogen atom,
[0164] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0165] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms,
[0166] - A group represented as Si(Rx)(Ry)(Rz),
[0167] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0168] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0169] In Si(Rx)(Ry)(Rz), Rx, Ry, and Rz are each independently
[0170] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or
[0171] It is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[0172] R 102 ~R 119 In the case of "substituted or non-substituted," the substituents are each independently
[0173] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0174] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms,
[0175] Substituted or unsubstituted phenyl group,
[0176] Substituted or unsubstituted biphenyl group,
[0177] Substituted or unsubstituted terphenyl group,
[0178] Substituted or unsubstituted naphthyl group,
[0179] Substituted or unsubstituted anthryl group,
[0180] Substituted or unsubstituted phenanthryl group,
[0181] Substituted or unsubstituted crisenyl group,
[0182] Substituted or unsubstituted triphenylenyl group,
[0183] Substituted or unsubstituted fluorenyl group,
[0184] Substituted or unsubstituted 9,9'-spirobifluorenyl group,
[0185] Substituted or unsubstituted 9,9-dimethylfluorenyl group,
[0186] It is a substituted or unsubstituted 9,9-diphenylfluorenyl group.
[0187] [Tuesday 6]
[0188]
[0189] (In the above general formulas (11) to (13) and (11A) to (13A), R 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A and R 31A ~R 37A Each independently
[0190] hydrogen atom,
[0191] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0192] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0193] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0194] R 11 ~R 15 , R 21 ~R 27 and R 31 ~R 37 In the case of "substituted or non-substituted," the substituents are each independently
[0195] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0196] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms,
[0197] Substituted or unsubstituted phenyl group,
[0198] Substituted or unsubstituted biphenyl group,
[0199] Substituted or unsubstituted terphenyl group,
[0200] Substituted or unsubstituted naphthyl group,
[0201] Substituted or unsubstituted anthryl group,
[0202] Substituted or unsubstituted phenanthryl group,
[0203] Substituted or unsubstituted crisenyl group,
[0204] Substituted or unsubstituted triphenylenyl group,
[0205] Substituted or unsubstituted fluorenyl group,
[0206] Substituted or unsubstituted 9,9'-spirobifluorenyl group,
[0207] A substituted or unsubstituted 9,9-dimethylfluorenyl group, or
[0208] It is a substituted or unsubstituted 9,9-diphenylfluorenyl group, and
[0209] R 11 ~R 15 Among them, one or more of the groups consisting of two or more adjacent groups do not combine with each other to form a single ring of substitution or non-substitution, and also do not form a condensed ring of substitution or non-substitution, and
[0210] R 11A ~R 15A Among them, one or more of the groups consisting of two or more adjacent groups do not combine with each other to form a single ring of substitution or non-substitution, and also do not form a condensed ring of substitution or non-substitution, and
[0211] R 21 ~R 27 Among them, one or more of the groups consisting of two or more adjacent groups do not combine with each other to form a single ring of substitution or non-substitution, and also do not form a condensed ring of substitution or non-substitution, and
[0212] R 21A ~R 27A Among them, one or more of the groups consisting of two or more adjacent groups do not combine with each other to form a single ring of substitution or non-substitution, and also do not form a condensed ring of substitution or non-substitution, and
[0213] R 31 ~R 37 Among them, one or more of the groups consisting of two or more adjacent groups do not combine with each other to form a single ring of substitution or non-substitution, and also do not form a condensed ring of substitution or non-substitution, and
[0214] R 31A ~R 37A Among them, one or more of the groups consisting of two or more adjacent groups do not combine with each other to form a single ring of substitution or non-substitution, and also do not form a condensed ring of substitution or non-substitution, and
[0215] Among the above general formulas (11) to (13) as L1, * indicates the position of combination with *a in the above general formula (120), and R 11 ~R 15 , R 21 ~R 27 and R 31 ~R 37 One of them is a single bond that binds to L2, and
[0216] Among the above general formulas (11A) to (13A) as L2, * indicates the position of combination with *b in the above general formula (120), and R 11A ~R 15A , R 21A ~R 27A and R 31A ~R 37A One of them is a single bond that binds to L1, and
[0217] However, R in L1 12 or R 14 When is a single bond that combines with L2, L2's R 11A , R 13A , R 15A , R 21A ~R 27A and R 31A ~R 37A One of them is a single bond that combines with L1, and
[0218] R in L1 11 or R 15 When is a single bond that combines with L2, L2's R 12A , R 13A , R 14A , R 21A ~R 27A and R 31A ~R 37AOne of them is a single bond that combines with L1, and
[0219] R in L1 13 When this is a single bond combining with L2, L2's R 11A , R 12A , R 14A , R 15A , R 21A ~R 27A and R 31A ~R 37A One of them is a single bond that combines with L1, and
[0220] R in L1 21 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 22A ~R 27A and R 31A ~R 37A One of them is a single bond that combines with L1, and
[0221] R in L1 22 When is a single bond that combines with L2, L2's R 11A ~R 15A , R 21A , R 23A ~R 27A and R 31A ~R 37A One of them is a single bond that combines with L1, and
[0222] R in L1 23 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 21A ~R 22A , R 24A ~R 27A and R 31A ~R 37A One of them is a single bond that combines with L1, and
[0223] R in L1 24 When is a single bond that combines with L2, L2's R 11A ~R 15A , R 21A ~R23A , R 25A ~R 27A and R 31A ~R 37A One of them is a single bond that combines with L1, and
[0224] R in L1 25 When is a single bond that combines with L2, L2's R 11A ~R 15A , R 21A ~R 24A , R 26A ~R 27A and R 31A ~R 37A One of them is a single bond that combines with L1, and
[0225] R in L1 26 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 21A ~R 25A , R 27A and R 31A ~R 37A One of them is a single bond that combines with L1, and
[0226] R in L1 27 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 21A ~R 26A and R 31A ~R 37A One of them is a single bond that combines with L1, and
[0227] R in L1 31 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 21A ~R 27A and R 32A ~R 37A One of them is a single bond that combines with L1, and
[0228] R in L1 32 When is a single bond that combines with L2, L2's R11A ~R 15A , R 21A ~R 27A , R 31A and R 33A ~R 37A One of them is a single bond that combines with L1, and
[0229] R in L1 33 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 21A ~R 27A , R 31A ~R 32A and R 34A ~R 37A One of them is a single bond that combines with L1, and
[0230] R in L1 34 When is a single bond that combines with L2, L2's R 11A ~R 15A , R 21A ~R 27A , R 31A ~R 33A and R 35A ~R 37A One of them is a single bond that combines with L1, and
[0231] R in L1 35 When is a single bond that combines with L2, L2's R 11A ~R 15A , R 21A ~R 27A , R 31A ~R 34A and R 36A ~R 37A One of them is a single bond that combines with L1, and
[0232] R in L1 36 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 21A ~R 27A , R 31A ~R 35A and R 37AOne of them is a single bond that combines with L1, and
[0233] R in L1 37 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 21A ~R 27A and R 31A ~R 36A One of them is a single bond that combines with L1.)
[0234] According to one aspect of the present invention, a compound represented by the following general formula (1), (2) or (3) is provided.
[0235] [Tuesday 7]
[0236]
[0237] (In the above general formulas (1) to (3),
[0238] R 111 ~R 119 and R 211 ~R 219 Each independently
[0239] hydrogen atom,
[0240] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0241] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms,
[0242] - A group represented as Si(Rx)(Ry)(Rz),
[0243] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0244] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0245] In Si(Rx)(Ry)(Rz), Rx, Ry, and Rz are each independently
[0246] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or
[0247] It is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[0248] In the above general formula (1),
[0249] R 11 and R 12 of, R 13 and R 14 of, R 21 and R 22 of, R 23 and R 24 One or more of the groups consisting of the
[0250] They combine with each other to form a substituted or unsubstituted single ring,
[0251] They combine with each other to form substituted or unsubstituted condensed rings, or
[0252] Without combining with each other,
[0253] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 11 , R 13 , R 21 and R 23 Each independently
[0254] hydrogen atom,
[0255] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0256] Substituted or unsubstituted phenyl group,
[0257] Substituted or unsubstituted biphenyl group,
[0258] Substituted or unsubstituted naphthyl group,
[0259] Substituted or unsubstituted phenanthryl group,
[0260] Substituted or unsubstituted fluorenyl group,
[0261] A substituted or unsubstituted 9,9'-spirobifluorenyl group, or
[0262] It is represented by the following general formula (4), and
[0263] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 12 , R 14 , R 22 and R 24 Each independently
[0264] hydrogen atom,
[0265] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0266] Substituted or unsubstituted biphenyl group,
[0267] Substituted or unsubstituted naphthyl group,
[0268] Substituted or unsubstituted phenanthryl group,
[0269] Substituted or unsubstituted fluorenyl group,
[0270] A substituted or unsubstituted 9,9'-spirobifluorenyl group, or
[0271] It is represented by the following general formula (4), and
[0272] However, R 11 ~R 14 and R 21 ~R 24 At least one of them is not a hydrogen atom, and
[0273] In the above general formulas (2) to (3),
[0274] R 31 ~R 33 , R 41 ~R 43 , R 51 ~R 54 and R 61 ~R 64 One or more of the groups consisting of two or more adjacent groups
[0275] They combine with each other to form a substituted or unsubstituted single ring,
[0276] They combine with each other to form substituted or unsubstituted condensed rings, or
[0277] Without combining with each other,
[0278] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 and R 61 ~R 64 Each independently
[0279] hydrogen atom,
[0280] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0281] Substituted or unsubstituted phenyl group,
[0282] Substituted or unsubstituted biphenyl group,
[0283] Substituted or unsubstituted naphthyl group,
[0284] Substituted or unsubstituted phenanthryl group,
[0285] Substituted or unsubstituted fluorenyl group,
[0286] A substituted or unsubstituted spirobifluorenyl group, or
[0287] It is represented by the following general formula (4), and
[0288] However, R 31 ~R 34 and R 41 ~R 44 At least one of them is not a hydrogen atom, and
[0289] R 51 ~R 54 and R 61 ~R 64 At least one of them is not a hydrogen atom,
[0290] R in the compound represented by the above general formula (1) 11 and R 13 The group of, and R 21 and R 23 The keys of are different keys, or R 12 and R 14 The group of, and R 22 and R24 The groups are different from each other,
[0291] R in the compound represented by the above general formula (2) 31 and R 41 The group of, and R 32 and R 42 of, R 33 and R 43 The group of, and R 34 and R 44 At least one of the groups is different from each other, and
[0292] R in the compound represented by the above general formula (3) 51 and R 61 The group of, and R 52 and R 62 of, R 53 and R 63 , and R 54 and R 64 At least one of the groups is different from the others.)
[0293] [Tue 8]
[0294]
[0295] (In the above general formula (4), X 13 Silver oxygen atoms, sulfur atoms, or NR 319 And,
[0296] R 311 ~R 318 One or more of the groups consisting of two or more adjacent groups
[0297] They combine with each other to form a substituted or unsubstituted single ring,
[0298] They combine with each other to form substituted or unsubstituted condensed rings, or
[0299] They do not combine with each other,
[0300] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 311 ~R 319 Each independently
[0301] hydrogen atom,
[0302] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0303] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms,
[0304] Substituted or unsubstituted phenyl group,
[0305] Substituted or unsubstituted biphenyl group,
[0306] Substituted or unsubstituted terphenyl group,
[0307] Substituted or unsubstituted naphthyl group,
[0308] Substituted or unsubstituted anthryl group,
[0309] Substituted or unsubstituted phenanthryl group,
[0310] Substituted or unsubstituted crisenyl group,
[0311] Substituted or unsubstituted triphenylenyl group,
[0312] Substituted or unsubstituted fluorenyl group,
[0313] Substituted or unsubstituted 9,9'-spirobifluorenyl group,
[0314] Substituted or unsubstituted 9,9-dimethylfluorenyl group,
[0315] It is a substituted or unsubstituted 9,9-diphenylfluorenyl group, and
[0316] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 311 ~R 319 One of them is R 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 and R 61 ~R 64 It is a single bond that bonds to at least one of them.)
[0317] (In the above general formulas (1) to (3), R 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 , R 61 ~R 64 , R 111 ~R 119 , R 211 ~R 219 and R 311 ~R 319 In the case of "substituted or non-substituted," the substituents are each independently
[0318] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0319] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms,
[0320] Substituted or unsubstituted phenyl group,
[0321] Substituted or unsubstituted biphenyl group,
[0322] Substituted or unsubstituted terphenyl group,
[0323] Substituted or unsubstituted naphthyl group,
[0324] Substituted or unsubstituted anthryl group,
[0325] Substituted or unsubstituted phenanthryl group,
[0326] Substituted or unsubstituted crisenyl group,
[0327] Substituted or unsubstituted triphenylenyl group,
[0328] Substituted or unsubstituted fluorenyl group,
[0329] Substituted or unsubstituted 9,9'-spirobifluorenyl group,
[0330] Substituted or unsubstituted 9,9-dimethylfluorenyl group,
[0331] It is a substituted or unsubstituted 9,9-diphenylfluorenyl group.
[0332] According to one aspect of the present invention,
[0333] Positive poles and,
[0334] cathode and,
[0335] It includes a light-emitting layer included between the anode and the cathode,
[0336] The above-mentioned light-emitting layer comprises, as a host material, a compound according to one embodiment of the present invention described above.
[0337] An organic electroluminescence device is provided.
[0338] According to one embodiment of the present invention, an organic electroluminescence device is provided having an anode, a cathode, a first light-emitting layer disposed between the anode and the cathode, and a second light-emitting layer disposed between the first light-emitting layer and the cathode, wherein the first light-emitting layer has at least one group represented by the following general formula (11) and also contains a first compound represented by the following general formula (1A) as a first host material, and the second light-emitting layer contains a second compound represented by the following general formula (2) as a second host material, and the first light-emitting layer and the second light-emitting layer are in direct contact.
[0339] [Tue 9]
[0340]
[0341] (In the above general formula (1A),
[0342] R 101 ~R 110 Each independently
[0343] hydrogen atom,
[0344] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0345] Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
[0346] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[0347] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[0348] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[0349] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[0350] -O-(R 904 The one indicated by ),
[0351] -S-(R 905 The one indicated by ),
[0352] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,
[0353] -C(=O)R 801 The one indicated by,
[0354] -COOR 802 The one indicated by,
[0355] Halogen atoms,
[0356] Cyanogi,
[0357] Nitro,
[0358] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
[0359] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, or
[0360] The above general formula (11) is a device represented by the above general formula,
[0361] However, R 101 ~R 110 At least one of them is a device represented by the above general formula (11), and
[0362] In the case where there are multiple devices represented by the above general formula (11), the multiple devices represented by the above general formula (11) are identical or different from each other,
[0363] L 101 silver
[0364] single bond,
[0365] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[0366] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0367] Ar 101 silver
[0368] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0369] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0370] mx is 0, 1, 2, 3, 4, or 5, and
[0371] L 101 If there are 2 or more of these, 2 or more L 101 They are identical or different from each other,
[0372] Ar 101 If 2 or more exist, 2 or more Ar 101 They are identical or different from each other,
[0373] In the above general formula (11), * indicates the bonding position with the pyrene ring in the above general formula (1A).
[0374] [Tuesday 10]
[0375]
[0376] (In the above general formula (2),
[0377] R 201 ~R 208 Each independently
[0378] hydrogen atom,
[0379] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0380] Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
[0381] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[0382] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[0383] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[0384] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[0385] -O-(R 904 The one indicated by ),
[0386] -S-(R 905 The one indicated by ),
[0387] -N(R 906 )(R 907 The one indicated by ),
[0388] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,
[0389] -C(=O)R 801 The one indicated by,
[0390] -COOR 802 The one indicated by,
[0391] Halogen atoms,
[0392] Cyanogi,
[0393] Nitro,
[0394] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0395] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0396] L 201 and L 202 Each independently
[0397] single bond,
[0398] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[0399] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0400] Ar 201 and Ar202 Each independently
[0401] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0402] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[0403] (Among the first compound represented by the above general formula (1A) and the second compound represented by the above general formula (2), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each independently
[0404] hydrogen atom,
[0405] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0406] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[0407] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0408] It is a complex circulating ring with 5 to 50 substituent or unsubstituent atoms, and
[0409] R 901 If this plural exists, the plural R 901 They are identical or different from each other,
[0410] R 902 If there are multiple instances of R 902 are identical or different from each other,
[0411] R 903 If this plural exists, the plural R 903 They are identical or different from each other,
[0412] R 904 If there are multiple instances of R 904are identical or different from each other,
[0413] R 905 If there are multiple instances of R 905 are identical or different from each other,
[0414] R 906 If this plural exists, the plural R 906 They are identical or different from each other,
[0415] R 907 If this plural exists, the plural R 907 They are identical or different from each other,
[0416] R 801 If this plural exists, the plural R 801 They are identical or different from each other,
[0417] R 802 If there are multiple instances of R 802 are identical or different from each other.
[0418] According to one aspect of the present invention, an electronic device equipped with an organic electroluminescence element according to one aspect of the present invention described above is provided.
[0419] According to one aspect of the present invention, a compound capable of improving luminous efficiency, an organic EL device using said compound, and an electronic device equipped with said organic EL device can be provided.
[0420] In addition, according to one embodiment of the present invention, an organic electroluminescence device with improved performance can be provided. In addition, according to one embodiment of the present invention, an organic electroluminescence device with improved luminous efficiency can be provided. In addition, according to one embodiment of the present invention, an electronic device equipped with said organic electroluminescence device can be provided. Brief explanation of the drawing
[0421] FIG. 1 is a diagram showing the schematic configuration of an example of an organic electroluminescence device according to a third embodiment of the present invention. FIG. 2 is a diagram showing the schematic configuration of an example of an organic electroluminescence device according to the fourth embodiment of the present invention. Specific details for implementing the invention
[0422] [definition]
[0423] In this specification, the term hydrogen atom includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.
[0424] In this specification, in the chemical structural formula, hydrogen atoms, i.e., light hydrogen atoms, deuterium atoms, or tritium atoms are bonded to the bondable positions where symbols such as "R" or "D" representing a deuterium atom are not specified.
[0425] In this specification, the ring-forming carbon number refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., monocyclic compounds, condensed-ring compounds, crosslinked compounds, carbon-ring compounds, and heterocyclic compounds). If the ring is substituted by a substituent, the carbons included in the substituent are not included in the ring-forming carbon number. Unless otherwise noted, the “ring-forming carbon number” described below shall be the same. For example, the benzene ring has a ring-forming carbon number of 6, the naphthalene ring has a ring-forming carbon number of 10, the pyridine ring has a ring-forming carbon number of 5, and the furan ring has a ring-forming carbon number of 4. In addition, for example, the ring-forming carbon number of a 9,9-diphenylfluorenyl group is 13, and the ring-forming carbon number of a 9,9'-spirobifluorenyl group is 25.
[0426] In addition, when a benzene ring is substituted with, for example, an alkyl group, the number of carbon atoms of this alkyl group is not included in the number of carbon atoms forming the ring of the benzene ring. Therefore, the number of carbon atoms forming the ring of the benzene ring substituted with an alkyl group is 6. In addition, when a naphthalene ring is substituted with, for example, an alkyl group, the number of carbon atoms of the alkyl group is not included in the number of carbon atoms forming the ring of the naphthalene ring. Therefore, the number of carbon atoms forming the ring of the naphthalene ring substituted with an alkyl group is 10.
[0427] In this specification, the number of ring-forming atoms refers to the number of atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., a single ring, a condensed ring, and a ring assembly) (e.g., a single ring compound, a condensed ring compound, a cross-linked compound, a carbon ring compound, and a complex ring compound). Atoms that do not constitute a ring (e.g., a hydrogen atom terminating the bond of an atom constituting a ring) or atoms included in a substituent when the ring is substituted by a substituent are not included in the number of ring-forming atoms. Unless otherwise noted, the "number of ring-forming atoms" described below shall be the same. For example, the number of ring-forming atoms of a pyridine ring is 6, the number of ring-forming atoms of a quinazolin ring is 10, and the number of ring-forming 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 ring-forming atoms of a pyridine ring. For this reason, the number of ring-forming atoms of a pyridine ring to which hydrogen atoms or substituents are bonded is 6. Also, for example, hydrogen atoms or atoms constituting substituents bonded to carbon atoms of a quinazoline ring are not included in the number of ring-forming atoms of the quinazoline ring. For this reason, the number of ring-forming atoms of a quinazoline ring to which hydrogen atoms or substituents are bonded is 10.
[0428] In the present specification, in the expression “substituted or unsubstituted ZZ group having XX to YY carbon atoms,” “XX to YY carbon atoms” indicates the number of carbon atoms when the ZZ group is unsubstituted and does not include the number of carbon atoms of the substituent when it is substituted. Here, “YY” is greater than “XX,” where “XX” means an integer of 1 or more, and “YY” means an integer of 2 or more.
[0429] In the present specification, the "number of atoms XX to YY" in the expression "ZZ group having XX to YY of substituted or unsubstituted atoms" represents the number of atoms when the ZZ group is unsubstituted and does not include the number of atoms of the substituent when it is substituted. Here, "YY" is greater than "XX," where "XX" means an integer greater than or equal to 1, and "YY" means an integer greater than or equal to 2.
[0430] In this specification, the term "unsubstituted ZZ group" indicates the case where the "substituted or unsubstituted ZZ group" is the "unsubstituted ZZ group," and the term "substituted ZZ group" indicates the case where the "substituted or unsubstituted ZZ group" is the "substituted ZZ group."
[0431] In this specification, "unsubstituted" in the case of "substituted or unsubstituted ZZ group" means that the hydrogen atoms in the ZZ group are not substituted with substituents. The hydrogen atoms in the "unsubstituted ZZ group" are light hydrogen atoms, deuterium atoms, or tritium atoms.
[0432] In addition, in the present specification, "substitution" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are substituted with substituents. Likewise, "substitution" in the case of "BB group substituted with AA group" means that one or more hydrogen atoms in the BB group are substituted with AA groups.
[0433] "Substituents described in this specification"
[0434] The substituents described in this specification will be explained below.
[0435] The number of ring-forming carbons of the “unsubstituted aryl group” described in this specification is 6 to 50 unless otherwise specified in this specification, preferably 6 to 30, more preferably 6 to 18.
[0436] The number of ring-forming atoms of the “unsubstituted complex ring” described in this specification is 5 to 50 unless otherwise specified in this specification, preferably 5 to 30, more preferably 5 to 18.
[0437] The number of carbon atoms of the “unsubstituted alkyl group” described in this specification is 1 to 50 unless otherwise specified in this specification, preferably 1 to 20, more preferably 1 to 6.
[0438] The number of carbon atoms of the “unsubstituted alkenyl group” described in this specification is 2 to 50 unless otherwise specified in this specification, preferably 2 to 20, more preferably 2 to 6.
[0439] The number of carbon atoms of the “unsubstituted alkynyl group” described in this specification is 2 to 50 unless otherwise specified in this specification, preferably 2 to 20, more preferably 2 to 6.
[0440] The number of ring-forming carbon atoms of the “unsubstituted cycloalkyl group” described in this specification is 3 to 50 unless otherwise specified in this specification, preferably 3 to 20, more preferably 3 to 6.
[0441] The number of ring-forming carbon atoms of the “unsubstituted arylene group” described in this specification is 6 to 50 unless otherwise specified in this specification, preferably 6 to 30, more preferably 6 to 18.
[0442] The number of ring-forming atoms of the “unsubstituted divalent complex circulator” described in this specification is 5 to 50 unless otherwise specified in this specification, preferably 5 to 30, more preferably 5 to 18.
[0443] The number of carbon atoms of the “unsubstituted alkylene group” described in this specification is 1 to 50 unless otherwise specified in this specification, preferably 1 to 20, more preferably 1 to 6.
[0444] · "Substitution or non-substitution aryl"
[0445] Specific examples (Group of Specific Examples G1) of the “substituted or unsubstituted aryl group” described in this specification include the following unsubstituted aryl group (Group of Specific Examples G1A) and substituted aryl group (Group of Specific Examples G1B) (wherein, “unsubstituted aryl group” refers to the case where the “substituted or unsubstituted aryl group” is a “unsubstituted aryl group,” and “substituted aryl group” refers to the case where the “substituted or unsubstituted aryl group” is a “substituted aryl group)). In this specification, when simply referred to as “aryl group,” both “unsubstituted aryl group” and “substituted aryl group” are included.
[0446] "Substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are substituted with substituents. Examples of "substituted aryl groups" include, for instance, a group in which one or more hydrogen atoms of an "unsubstituted aryl group" of the following Specific Example Group G1A are substituted with substituents, and examples of substituted aryl groups of the following Specific Example Group G1B. Furthermore, the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed herein are merely examples, and the "substituted aryl groups" described in this specification include a group in which a hydrogen atom bonded to the carbon atom of the aryl group itself in the "substituted aryl group" of the following Specific Example Group G1B is further substituted with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted aryl group" of the following Specific Example Group G1B is further substituted with a substituent.
[0447] ·Muchan's Arilgi (Special Example Group G1A):
[0448] phenyl group,
[0449] p-biphenyl group,
[0450] m-biphenyl group,
[0451] o-biphenyl group,
[0452] p-terphenyl-4-diary,
[0453] p-terphenyl-3-diary,
[0454] p-terphenyl-2-diary,
[0455] m-terphenyl-4-diary,
[0456] m-terphenyl-3-diary,
[0457] m-terphenyl-2-diary,
[0458] o-terphenyl-4-diary,
[0459] o-terphenyl-3-diary,
[0460] o-terphenyl-2-diyl,
[0461] 1-Naphthyl group,
[0462] 2-Naphthyl group,
[0463] Anthrill,
[0464] Benzoanthryl group,
[0465] phenanthril group,
[0466] Benzophenanthrile group,
[0467] Penalenyl group,
[0468] Pyreneyl group,
[0469] Crysenyl group,
[0470] benzocrysenyl group,
[0471] triphenylenyl group,
[0472] benzotriphenylenyl group,
[0473] tetracenyl group,
[0474] Pentacenyl group,
[0475] Fluorenyl group,
[0476] 9,9'-spirobifluorenyl group,
[0477] benzofluorenyl group,
[0478] dibenzofluorenyl group,
[0479] Fluoranthenyl group,
[0480] benzofluranthenyl group,
[0481] perylenyl group, and
[0482] A monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).
[0483] [Tuesday 11]
[0484]
[0485] [Tuesday 12]
[0486]
[0487] · Substitution Aryl group (Specific example group G1B):
[0488] o-tollil group,
[0489] m-tolyl group,
[0490] p-tolyl group,
[0491] Para-xyl group,
[0492] meta-xylyl group,
[0493] Ortho-xyl group,
[0494] para-isopropylphenyl group,
[0495] meta-isopropylphenyl group,
[0496] Ortho-isopropylphenyl group,
[0497] para-t-butylphenyl group,
[0498] meta-t-butylphenyl group,
[0499] Ortho-t-butylphenyl group,
[0500] 3,4,5-trimethylphenyl group,
[0501] 9,9-dimethylfluorenyl group,
[0502] 9,9-diphenylfluorenyl group
[0503] 9,9-bis(4-methylphenyl)fluorenyl group,
[0504] 9,9-bis(4-isopropylphenyl)fluorenyl group,
[0505] 9,9-bis(4-t-butylphenyl)fluorenyl group,
[0506] cyanophenyl group,
[0507] triphenylsilylphenyl group,
[0508] trimethylsilylphenyl group,
[0509] phenylnaphthyl group,
[0510] Naphthylphenyl group, and
[0511] A group in which one or more hydrogen atoms of a monovalent group derived from a ring structure represented by the above general formulas (TEMP-1) to (TEMP-15) are substituted with substituents.
[0512] · "Substitutional or Non-substitutional Complex Recall"
[0513] The “complex circulating group” described in this specification is a cyclic group comprising at least one heteroatom in a ring-forming atom. Specific examples of heteroatoms include nitrogen atoms, oxygen atoms, sulfur atoms, silicon atoms, phosphorus atoms, and boron atoms.
[0514] The “complex ring” described in this specification is a simple ring or a condensed ring.
[0515] The “complex generator” described in this specification is an aromatic complex generator or a non-aromatic complex generator.
[0516] Examples of specific examples (group of specific examples G2) of the “complex circulator with or without permutation” described in this specification include the following complex circulators with or without permutation (group of specific examples G2A) and complex circulators with permutation (group of specific examples G2B) (wherein, a complex circulator with or without permutation refers to the case where the “complex circulator with or without permutation” is a “complex circulator with or without permutation,” and a complex circulator with permutation refers to the case where the “complex circulator with or without permutation” is a “complex circulator with permutation.”). In this specification, when simply referred to as a “complex circulator,” it includes both a “complex circulator with or without permutation” and a “complex circulator with permutation.”
[0517] "Substituted complex sphere" refers to a group in which one or more hydrogen atoms of a "non-substituted complex sphere" are substituted with substituents. Specific examples of a "substituted complex sphere" include a group in which a hydrogen atom of a "non-substituted complex sphere" of the following group of examples G2A is substituted, and an example of a substituted complex sphere of the following group of examples G2B. Furthermore, the examples of "non-substituted complex spheres" and "substituted complex spheres" listed herein are merely examples, and the "substituted complex spheres" described in this specification include a group in which a hydrogen atom bonded to the ring-forming atom of the complex sphere itself in the "substituted complex sphere" of the following group of examples G2B is further substituted with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted complex sphere" of the following group of examples G2B is further substituted with a substituent.
[0518] Specific example group G2A includes, for example, an unsubstituted complex group containing a nitrogen atom (Specific example group G2A1), an unsubstituted complex group containing an oxygen atom (Specific example group G2A2), an unsubstituted complex group containing a sulfur atom (Specific example group G2A3), and a monovalent complex group (Specific example group G2A4) derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33).
[0519] Specific example group G2B includes, for example, a substituent complex group containing a nitrogen atom (Specific example group G2B1), a substituent complex group containing an oxygen atom (Specific example group G2B2), a substituent complex group containing a sulfur atom (Specific example group G2B3), and a group in which one or more hydrogen atoms are substituted as substituents among monovalent complex groups derived from ring structures represented by the following general formulas (TEMP-16) to (TEMP-33).
[0520] · Unsubstituted complex saturators containing nitrogen atoms (Specific example group G2A1):
[0521] pyrrolyl group,
[0522] Imidajorilgi,
[0523] pyrazolyl group,
[0524] triazolyl group,
[0525] tetrazolyl group,
[0526] Oxazoligi,
[0527] Isooxazolilgi,
[0528] Oxadiazolyl group,
[0529] Thiazolyl group,
[0530] isothiazolyl group,
[0531] Thiadiazolylgi,
[0532] Piridilgi,
[0533] Piridajinilgi,
[0534] pyrimidinyl group,
[0535] Pyrazinyl group,
[0536] triazinyl group,
[0537] Indolil,
[0538] Isoindolilgi,
[0539] Indolezinyl group,
[0540] Quinolidinyl group,
[0541] Quinolyl group,
[0542] isoquinolyl group,
[0543] Sinnolilgi,
[0544] Phthalaginyl group,
[0545] Quinazolinyl group,
[0546] Quinoxalinyl group,
[0547] benzimidazolyl group,
[0548] Indazolillgi,
[0549] phenanthrolinyl group,
[0550] phenanthridinyl group,
[0551] Acridinyl group,
[0552] phenazinyl group,
[0553] Carbazolyl group,
[0554] benzocarbazolyl group,
[0555] Morpolinogi,
[0556] phenoxazinyl group,
[0557] Phenothiazinyl group,
[0558] Azacarbazolyl group and diazcarbazolyl group.
[0559] · Unsubstituted complex mutators containing oxygen atoms (Specific example group G2A2):
[0560] Purilgi,
[0561] Oxazoligi,
[0562] Isooxazolilgi,
[0563] Oxadiazolyl group,
[0564] xanthenyl group,
[0565] benzofuranyl group,
[0566] isobenzofuranyl group,
[0567] dibenzofuranyl group,
[0568] Naphthobenzofuranyl group,
[0569] Benzooxazolyl group,
[0570] Benzoisooxazolyl group,
[0571] phenoxazinyl group,
[0572] Morpolinogi,
[0573] dinaphthofranyl group,
[0574] Azadibenzofuranyl group,
[0575] Diazadibenzofuranyl group,
[0576] Azanaptobenzofuranyl group, and
[0577] Diazanaptobenzofuranyl group.
[0578] · Unsubstitutable complex circulators containing sulfur atoms (Specific example group G2A3):
[0579] thienyl group,
[0580] Thiazolyl group,
[0581] isothiazolyl group,
[0582] Thiadiazolylgi,
[0583] benzothiophenyl group (benzothienyl group),
[0584] isobenzothiophenyl group (isobenzothienyl group),
[0585] dibenzothiophenyl group (dibenzothienyl group),
[0586] Naphthobenzothiophenyl group (naphthobenzothienyl group),
[0587] benzothiazolyl group,
[0588] Benzoisothiazolyl group,
[0589] Phenothiazinyl group,
[0590] dinaphthothiophenyl group (dinaphthienyl group),
[0591] Azadibenzothiophenyl group (azadibenzothienyl group),
[0592] Diazadibenzothiophenyl group (diazadibenzothienyl group),
[0593] Azanapthobenzothiophenyl group (azanaphthobenzothienyl group), and
[0594] Diazanaptobenzothiophenyl group (diazanaptobenzothienyl group).
[0595] · A monovalent complex circulator induced by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):
[0596] [Tuesday 13]
[0597]
[0598] [Tuesday 14]
[0599]
[0600] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each is independently an oxygen atom, a sulfur atom, NH, or CH2. However, X A and Y AAt least one of them is an oxygen atom, a sulfur atom, or NH.
[0601] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A In cases where at least one of them is NH or CH2, the monovalent complex circulating group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.
[0602] · Substitutional complex vacancies containing nitrogen atoms (Specific example group G2B1):
[0603] (9-phenyl)carbazolyl group,
[0604] (9-biphenylyl)carbazolyl group,
[0605] (9-phenyl)phenylcarbazolyl group,
[0606] (9-naphthyl)carbazolyl group,
[0607] Diphenylcarbazole-9-diary,
[0608] Phenylcarbazole-9-diary,
[0609] methylbenzimidazolyl group,
[0610] Ethylbenzimidazolyl group,
[0611] phenyltriazinyl group,
[0612] biphenyltriazinyl group,
[0613] diphenyltriazinyl group,
[0614] Phenylquinazolinyl group, and
[0615] Biphenylquinazolinyl group.
[0616] · Substitutional complex mutators containing oxygen atoms (Specific example group G2B2):
[0617] Phenyldibenzofuranyl group,
[0618] methyldibenzofuranyl group,
[0619] t-butyldibenzofuranyl group, and
[0620] The monovalent residue of spiro[9H-xanthen-9,9'-[9H]fluorene].
[0621] · Complex substitutions containing sulfur atoms (Specific example group G2B3):
[0622] Phenyldibenzothiophenyl group,
[0623] methyldibenzothiophenyl group,
[0624] t-butyldibenzothiophenyl group, and
[0625] A monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].
[0626] · A group in which one or more hydrogen atoms of a monovalent complex cyclic group derived from the above general formulas (TEMP-16) to (TEMP-33) are substituted with substituents (Specific Example Group G2B4):
[0627] The above “one or more hydrogen atoms of a monovalent complex group” means one or more hydrogen atoms selected from a hydrogen atom bonded to a ring-forming carbon atom of the monovalent complex group, a hydrogen atom bonded to a nitrogen atom when at least one of XA and YA is NH, and a hydrogen atom of a methylene group when one of XA and YA is CH2.
[0628] · Substituted or unsubstituted alkyl group
[0629] Examples of specific examples (Group of Specific Examples G3) of the “substituted or unsubstituted alkyl group” described in this specification include the following unsubstituted alkyl group (Group of Specific Examples G3A) and substituted alkyl group (Group of Specific Examples G3B) (wherein, “unsubstituted alkyl group” refers to the case where the “substituted or unsubstituted alkyl group” is an “unsubstituted alkyl group,” and “substituted alkyl group” refers to the case where the “substituted or unsubstituted alkyl group” is a “substituted alkyl group.”). Hereinafter, when simply referred to as “alkyl group,” both the “unsubstituted alkyl group” and the “substituted alkyl group” are included.
[0630] "Substituted alkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are substituted with substituents. Specific examples of "substituted alkyl group" include the group in which one or more hydrogen atoms in the following "unsubstituted alkyl group" (Specific Example Group G3A) are substituted with substituents, and examples of a substituted alkyl group (Specific Example Group G3B). In this specification, the alkyl group in "unsubstituted alkyl group" refers to a chain-type alkyl group. Accordingly, "unsubstituted alkyl group" includes straight-chain "unsubstituted alkyl groups" and branched "unsubstituted alkyl groups." In addition, the examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed herein are merely examples, and the "substituted alkyl groups" described in this specification include groups in which the hydrogen atom of the alkyl group itself in the "substituted alkyl group" of Specific Example Group G3B is further substituted with a substituent, and groups in which the hydrogen atom of the substituent in the "substituted alkyl group" of Specific Example Group G3B is further substituted with a substituent.
[0631] · Unsubstituted alkyl group (Specific Example Group G3A):
[0632] methyl group,
[0633] ethyl group,
[0634] n-Profilter,
[0635] isopropyl group,
[0636] n-butyl group,
[0637] isobutyl group,
[0638] s-butyl group and t-butyl group.
[0639] · Substituted alkyl group (Specific Example Group G3B):
[0640] heptafluoropropyl group (including isomers),
[0641] pentafluoroethyl group,
[0642] 2,2,2-trifluoroethyl group, and
[0643] Trifluoromethyl group.
[0644] · "Substituted or unsubstituted alkenyl group"
[0645] Examples of specific examples (Group of Specific Examples G4) of the “substituted or unsubstituted alkenyl group” described in this specification include the following unsubstituted alkenyl group (Group of Specific Examples G4A) and substituted alkenyl group (Group of Specific Examples G4B) (wherein, “unsubstituted alkenyl group” refers to the case where the “substituted or unsubstituted alkenyl group” is the “unsubstituted alkenyl group,” and “substituted alkenyl group” refers to the case where the “substituted or unsubstituted alkenyl group” is the “substituted alkenyl group)). In this specification, when simply referred to as “alkenyl group,” it includes both the “unsubstituted alkenyl group” and the “substituted alkenyl group.”
[0646] "Substituted alkenyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are substituted with substituents. Specific examples of "substituted alkenyl groups" include the following "unsubstituted alkenyl groups" (Group of Specific Examples G4A) having substituents and examples of substituted alkenyl groups (Group of Specific Examples G4B). Furthermore, the examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed herein are merely examples, and the "substituted alkenyl groups" described in this specification include a group in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl group" of Group of Specific Examples G4B is further substituted with substituents, and a group in which a hydrogen atom of a substituent in the "substituted alkenyl group" of Group of Specific Examples G4B is further substituted with substituents.
[0647] · Non-substitutional alkenyl group (Special Example Group G4A):
[0648] vinyl,
[0649] Alilgi,
[0650] 1-butenyl group,
[0651] 2-butenyl group, and
[0652] 3-butenyl group.
[0653] · Substitutional alkenyl group (Specific example group G4B):
[0654] 1,3-butanedienyl group,
[0655] 1-methylvinyl group,
[0656] 1-methylallyl group,
[0657] 1,1-dimethylallyl group,
[0658] 2-methylallyl group, and
[0659] 1,2-dimethylallyl group.
[0660] · "Substituted or unsubstituted alkynyl group"
[0661] Examples of specific examples (Group of Examples G5) of the “substituted or unsubstituted alkynyl group” described in this specification include the following unsubstituted alkynyl group (Group of Examples G5A), etc. (wherein, “unsubstituted alkynyl group” refers to the case where the “substituted or unsubstituted alkynyl group” is the “unsubstituted alkynyl group.”). Hereinafter, when simply referred to as “alkynyl group,” both the “unsubstituted alkynyl group” and the “substituted alkynyl group” are included.
[0662] "Substituted alkynyl group" means a group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" are substituted with substituents. Specific examples of "substituted alkynyl group" include the group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" (Specific Example Group G5A) below are substituted with substituents.
[0663] · Unsubstituted alkynyl group (Specific example group G5A): ethinyl group
[0664] · Substituted or unsubstituted cycloalkyl group
[0665] Examples of specific examples (Group of Specific Examples G6) of the “substituted or unsubstituted cycloalkyl group” described in this specification include the following unsubstituted cycloalkyl group (Group of Specific Examples G6A) and substituted cycloalkyl group (Group of Specific Examples G6B) (wherein, “unsubstituted cycloalkyl group” refers to the case where the “substituted or unsubstituted cycloalkyl group” is an “unsubstituted cycloalkyl group,” and “substituted cycloalkyl group” refers to the case where the “substituted or unsubstituted cycloalkyl group” is a “substituted cycloalkyl group.”). In this specification, when simply referred to as “cycloalkyl group,” it includes both the “unsubstituted cycloalkyl group” and the “substituted cycloalkyl group.”
[0666] "Substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are substituted with substituents. Specific examples of "substituted cycloalkyl groups" include a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" (Specific Example Group G6A) are substituted with substituents, and examples of a substituted cycloalkyl group (Specific Example Group G6B). Furthermore, the examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed herein are merely examples, and the "substituted cycloalkyl groups" described in this specification include a group in which one or more hydrogen atoms bonded to the carbon atoms of the cycloalkyl group itself in the "substituted cycloalkyl group" of Specific Example Group G6B are substituted with substituents, and a group in which a hydrogen atom of a substituent in the "substituted cycloalkyl group" of Specific Example Group G6B is further substituted with a substituent.
[0667] · Unsubstituted cycloalkyl group (Specific Example Group G6A):
[0668] cyclopropyl group,
[0669] cyclobutyl group,
[0670] Cyclopentyl group,
[0671] cyclohexyl group,
[0672] 1-adamantyl group,
[0673] 2-adamantyl group,
[0674] 1-norbornyl group, and
[0675] 2-Norbornilgi.
[0676] · Substituted cycloalkyl group (Specific Example Group G6B):
[0677] 4-methylcyclohexyl group.
[0678] ·「-Si(R 901 )(R 902 )(R 903 The device indicated by )
[0679] -Si(R as described in this specification 901 )(R 902 )(R 903 As for a specific example of the device indicated by ) (specific example group G7),
[0680] -Si(G1)(G1)(G1),
[0681] -Si(G1)(G2)(G2),
[0682] -Si(G1)(G1)(G2),
[0683] -Si(G2)(G2)(G2),
[0684] -Si(G3)(G3)(G3), and
[0685] -Si(G6)(G6)(G6)
[0686] ...can be cited. Here,
[0687] G1 is a “substituted or non-substituted aryl group” as described in Specific Example Group G1.
[0688] G2 is a "complex circulator of permutation or non-permutation" described in the specific example group G2.
[0689] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.
[0690] G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Example Group G6.
[0691] In -Si(G1)(G1)(G1), the multiple G1s are either identical or different from each other.
[0692] In -Si(G1)(G2)(G2), the multiple G2s are either identical or different from each other.
[0693] In -Si(G1)(G1)(G2), the multiple G1s are either identical or different from each other.
[0694] In -Si(G2)(G2)(G2), the multiple G2s are either identical or different from each other.
[0695] In -Si(G3)(G3)(G3), the multiple G3s are either identical or different from each other.
[0696] In -Si(G6)(G6)(G6), the multiple G6s are either identical or different from each other.
[0697] ·「-O-(R 904 The unit indicated by )
[0698] -O-(R as described in this specification 904 As for a specific example of the device indicated by ) (specific example group G8),
[0699] -O(G1),
[0700] -O(G2),
[0701] -O(G3), and
[0702] -O(G6)
[0703] ...can be cited.
[0704] Here,
[0705] G1 is a “substituted or non-substituted aryl group” as described in Specific Example Group G1.
[0706] G2 is a "complex circulator of permutation or non-permutation" described in the specific example group G2.
[0707] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.
[0708] G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Example Group G6.
[0709] ·「-S-(R 905 The unit indicated by )
[0710] -S-(R as described in this specification 905 As for a specific example of the device indicated by ) (specific example group G9),
[0711] -S(G1),
[0712] -S(G2),
[0713] -S(G3), and
[0714] -S(G6)
[0715] ...can be cited.
[0716] Here,
[0717] G1 is a “substituted or non-substituted aryl group” as described in Specific Example Group G1.
[0718] G2 is a "complex circulator of permutation or non-permutation" described in the specific example group G2.
[0719] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.
[0720] G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Example Group G6.
[0721] ·「-N(R 906 )(R 907 The unit indicated by )
[0722] -N(R as described in this specification 906 )(R 907 As for a specific example of the device indicated by ) (specific example group G10),
[0723] -N(G1)(G1),
[0724] -N(G2)(G2),
[0725] -N(G1)(G2),
[0726] -N(G3)(G3), and
[0727] -N(G6)(G6)
[0728] ...can be cited.
[0729] Here,
[0730] G1 is a “substituted or non-substituted aryl group” as described in Specific Example Group G1.
[0731] G2 is a "complex circulator of permutation or non-permutation" described in the specific example group G2.
[0732] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.
[0733] G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Example Group G6.
[0734] In -N(G1)(G1), multiple G1s are identical or different from each other.
[0735] In -N(G2)(G2), multiple G2s are identical or different from each other.
[0736] In -N(G3)(G3), multiple G3s are either identical or different from each other.
[0737] In -N(G6)(G6), multiple G6s are either identical or different from each other.
[0738] · "Halogen atom"
[0739] Specific examples of the “halogen atoms” described in this specification (Specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.
[0740] · "Substituted or unsubstituted fluoroalkyl group"
[0741] 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 substituted with a fluorine atom, and also includes a group (perfluoro group) in which all hydrogen atoms bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" are substituted with fluorine atoms. Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of the "fluoroalkyl group" are substituted with a substituent. In addition, the “substituted fluoroalkyl group” described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the “substituted fluoroalkyl group” are further substituted with a substituent, and a group in which one or more hydrogen atoms of the substituent in the “substituted fluoroalkyl group” are further substituted with a substituent. Specific examples of the “unsubstituted fluoroalkyl group” include a group in which one or more hydrogen atoms in the “alkyl group” (specific example group G3) are substituted with a fluorine atom.
[0742] · "Substituted or unsubstituted haloalkyl group"
[0743] 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 substituted with a halogen atom, and includes a group in which all hydrogen atoms bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" are substituted with halogen atoms. Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of the "haloalkyl group" are substituted with a substituent. In addition, the “substituted haloalkyl group” described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the “substituted haloalkyl group” are further substituted with a substituent, and a group in which one or more hydrogen atoms of the substituent in the “substituted haloalkyl group” are further substituted with a substituent. Specific examples of the “unsubstituted haloalkyl group” include a group in which one or more hydrogen atoms in the “alkyl group” (specific example group G3) are substituted with a halogen atom. A haloalkyl group may be referred to as an alkyl halide group.
[0744] · "Substitutional or non-substitutional alkoxyl group"
[0745] A specific example of the “substituted or unsubstituted alkoxy group” described in this specification is a group represented by -O(G3), where G3 is the “substituted or unsubstituted alkyl group” described in the group of specific examples G3. The number of carbon atoms of the “unsubstituted alkoxy group” is 1 to 50 unless otherwise specified in this specification, preferably 1 to 30, and more preferably 1 to 18.
[0746] · "Substituted or unsubstituted alkylthio groups"
[0747] A specific example of the “substituted or unsubstituted alkylthio group” described in this specification is a group represented by -S(G3), where G3 is the “substituted or unsubstituted alkyl group” described in the group of specific examples G3. The number of carbon atoms of the “unsubstituted alkylthio group” is 1 to 50 unless otherwise specified in this specification, preferably 1 to 30, and more preferably 1 to 18.
[0748] · "Substituted or unsubstituted aryloxy groups"
[0749] A specific example of the “substituted or unsubstituted aryloxy group” described in this specification is a group represented by -O(G1), where G1 is the “substituted or unsubstituted aryl group” described in the group of specific examples G1. The number of ring-forming carbons of the “unsubstituted aryloxy group” is 6 to 50 unless otherwise specified in this specification, preferably 6 to 30, and more preferably 6 to 18.
[0750] · "Substitution or non-substitution arylthioge"
[0751] A specific example of the “substituted or unsubstituted arylthio group” described in this specification is a group represented by -S(G1), where G1 is the “substituted or unsubstituted aryl group” described in the group of specific examples G1. The number of ring-forming carbons of the “unsubstituted arylthio group” is 6 to 50 unless otherwise specified in this specification, preferably 6 to 30, and more preferably 6 to 18.
[0752] · Substituted or unsubstituted trialkylsilyl group
[0753] A specific example of the “trialkylsilyl group” described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a “substituted or unsubstituted alkyl group” described in the group of specific examples G3. In -Si(G3)(G3)(G3), the plurality of G3s may be identical or different from each other. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the “trialkylsilyl group” is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.
[0754] · "Substitution or non-substitution Aralkilgi"
[0755] A specific example of the “substituted or unsubstituted aralkyl group” described in this specification is a group represented by -(G3)-(G1), wherein G3 is the “substituted or unsubstituted alkyl group” described in the group of specific examples G3, and G1 is the “substituted or unsubstituted aryl group” described in the group of specific examples G1. Accordingly, the “aralkyl group” is a group in which a hydrogen atom of the “alkyl group” is substituted with an “aryl group” as a substituent, and is one embodiment of the “substituted alkyl group.” The “unsubstituted aralkyl group” is the “unsubstituted alkyl group” substituted with the “unsubstituted aryl group,” and the number of carbon atoms of the “unsubstituted aralkyl group” is 7 to 50 unless otherwise specified in this specification, preferably 7 to 30, and more preferably 7 to 18.
[0756] Specific examples of “substituted or unsubstituted aralkyl groups” include benzyl groups, 1-phenylethyl groups, 2-phenylethyl groups, 1-phenylisopropyl groups, 2-phenylisopropyl groups, phenyl-t-butyl groups, α-naphthylmethyl groups, 1-α-naphthylethyl groups, 2-α-naphthylethyl groups, 1-α-naphthylisopropyl groups, 2-α-naphthylisopropyl groups, β-naphthylmethyl groups, 1-β-naphthylethyl groups, 2-β-naphthylethyl groups, 1-β-naphthylisopropyl groups, and 2-β-naphthylisopropyl groups.
[0757] The substituted or unsubstituted aryl groups described in this specification are, unless otherwise specified in this specification, preferably phenyl groups, p-biphenyl groups, m-biphenyl groups, o-biphenyl groups, p-terphenyl-4-yl groups, p-terphenyl-3-yl groups, p-terphenyl-2-yl groups, m-terphenyl-4-yl groups, m-terphenyl-3-yl groups, m-terphenyl-2-yl groups, o-terphenyl-4-yl groups, o-terphenyl-3-yl groups, o-terphenyl-2-yl groups, 1-naphthyl groups, 2-naphthyl groups, anthryl groups, phenanthryl groups, pyrenyl groups, crisenyl groups, triphenylenyl groups, fluorenyl groups, 9,9'-spirobifluorenyl groups, 9,9-dimethylfluorenyl groups, and 9,9-diphenylfluorenyl groups, etc.
[0758] The substituted or unsubstituted complex groups described herein, unless otherwise specified herein, are preferably pyridyl groups, pyrimidinyl groups, triazinyl groups, quinolyl groups, isoquinolyl groups, quinazolinyl groups, benzimidazolyl groups, phenanthrolinyl groups, carbazolyl groups (1-carbazolyl groups, 2-carbazolyl groups, 3-carbazolyl groups, 4-carbazolyl groups or 9-carbazolyl groups), benzocarbazolyl groups, azacarbazolyl groups, diazacarbazolyl groups, dibenzofuranyl groups, naphthobenzofuranyl groups, azadibenzofuranyl groups, diazadibenzofuranyl groups, dibenzothiophenyl groups, naphthobenzothiophenyl groups, azadibenzothiophenyl groups, diazadibenzothiophenyl groups, (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group or (9-phenyl)carbazol-4-yl group), (9-biphenyllil)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylliltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group and phenyldibenzothiophenyl group, etc.
[0759] In this specification, the carbazolyl group is, specifically, any one of the following, unless otherwise specified in this specification.
[0760] [Tuesday 15]
[0761]
[0762] In this specification, the (9-phenyl)carbazolyl group is, specifically, any one of the following groups, unless otherwise specified in this specification.
[0763] [Tuesday 16]
[0764]
[0765] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.
[0766] In this specification, the dibenzofuranyl group and the dibenzothiophenyl group are, specifically, any one of the following groups, unless otherwise specified in this specification.
[0767] [Tuesday 17]
[0768]
[0769] In the above general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.
[0770] The substituted or unsubstituted alkyl groups described in this specification are, unless otherwise specified in this specification, preferably methyl groups, ethyl groups, propyl groups, isopropyl groups, n-butyl groups, isobutyl groups, and t-butyl groups, etc.
[0771] · "Substitutional or non-substitutional arylen groups"
[0772] The “substituted or unsubstituted arylene group” described in this specification is a divalent group derived by removing one hydrogen atom from the aryl ring from the “substituted or unsubstituted aryl group” unless otherwise noted. Specific examples of the “substituted or unsubstituted arylene group” (Specific Example Group G12) include a divalent group derived by removing one hydrogen atom from the aryl ring from the “substituted or unsubstituted aryl group” described in Specific Example Group G1.
[0773] · "Divination of Substitution or Non-Substitution of a Bivalent Complex Call"
[0774] The “substituted or unsubstituted divalent complex ring” described in this specification is, unless otherwise noted, a divalent ring derived by removing one hydrogen atom from the “substituted or unsubstituted complex ring”. Specific examples of the “substituted or unsubstituted divalent complex ring” (Specific Example Group G13) include a divalent ring derived by removing one hydrogen atom from the “substituted or unsubstituted complex ring” described in Specific Example Group G2.
[0775] · "Substituted or unsubstituted alkylene group"
[0776] The “substituted or unsubstituted alkylene group” described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the “substituted or unsubstituted alkyl group” unless otherwise specified. Specific examples of the “substituted or unsubstituted alkylene group” (Specific Example Group G14) include a divalent group derived by removing one hydrogen atom on the alkyl chain from the “substituted or unsubstituted alkyl group” described in Specific Example Group G3.
[0777] The substituted or unsubstituted arylene groups described in this specification are, unless otherwise specified in this specification, preferably any one of the following general formulas (TEMP-42) to (TEMP-68).
[0778] [Tuesday 18]
[0779]
[0780] [Tue 19]
[0781]
[0782] Among the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.
[0783] In the above general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.
[0784] [Tue 20]
[0785]
[0786] Among the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.
[0787] Formula Q9 and Q 10 They may also join together through single bonds to form a ring.
[0788] In the above general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.
[0789] [Tue 21]
[0790]
[0791] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently hydrogen atoms or substituents.
[0792] In the above general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.
[0793] The bivalent complex ring with or without substitution described in this specification is preferably one of the following general formulas (TEMP-69) to (TEMP-102), unless otherwise specified in this specification.
[0794] [Tue 22]
[0795]
[0796] [Tue 23]
[0797]
[0798] [Tue 24]
[0799]
[0800] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently hydrogen atoms or substituents.
[0801] [Tue 25]
[0802]
[0803] [Tue 26]
[0804]
[0805] [Tue 27]
[0806]
[0807] [Tue 28]
[0808]
[0809] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently hydrogen atoms or substituents.
[0810] The above is an explanation of the “substituents described in this specification.”
[0811] · "When combined to form a ring"
[0812] In the present specification, the phrase “one or more of two or more adjacent groups combine to form a substituted or non-substituted ring, combine to form a substituted or non-substituted condensed ring, or do not combine to each other” means the case where “one or more of two or more adjacent groups combine to form a substituted or non-substituted ring,” the case where “one or more of two or more adjacent groups combine to form a substituted or non-substituted condensed ring,” and the case where “one or more of two or more adjacent groups do not combine to each other.”
[0813] The following describes cases in this specification where "one or more groups of two or more adjacent groups combine to form a substituted or unsubstituted single ring" and "one or more groups of two or more adjacent groups combine to form a substituted or unsubstituted condensed ring" (hereinafter, these cases may be collectively referred to as "combining to form a ring"). The explanation is given by taking the case of an anthracene compound represented by the following general formula (TEMP-103), in which the matrix is an anthracene ring, as an example.
[0814] [Tue 29]
[0815]
[0816] For example, R 921 ~R 930In the case where "one or more sets of two or more adjacent groups combine to form a ring," the two adjacent groups that make up one set are R 921 and R 922 of, R 922 and R 923 of, R 923 and R 924 of, R 924 and R 930 of, R 930 and R 925 of, R 925 and R 926 of, R 926 and R 927 of, R 927 and R 928 of, R 928 and R 929 The group of, and R 929 and R 921 It is the group of.
[0817] The above "one or more sets" means that two or more sets of the above two or more adjacent sets may simultaneously form a ring. For example, R 921 and R 922 They combine with each other to form the ring Q A Forms, and simultaneously R 925 and R 926 These combine with each other to form the ring Q B In the case where it is formed, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).
[0818] [Tue 30]
[0819]
[0820] The case where "a group consisting of two or more adjacent units" forms a ring includes not only the case where a group consisting of "two" adjacent units combines as in the example above, but also the case where a group consisting of "three or more" adjacent units combines. For example, R 921 and R 922 They combine with each other to form the ring QA It forms, and also R 922 and R 923 These combine with each other to form the ring Q C Forms, and 3 adjacent (R 921 , R 922 and R 923 This refers to the case where groups consisting of ) combine with each other to form a ring and condense onto the anthracene matrix, and in this case, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C is R 922 Share.
[0821] [Tue 31]
[0822]
[0823] The formed "single ring" or "condensed ring" is a structure consisting solely of the formed ring, and may be a saturated ring or an unsaturated ring. Even if "a set of two adjacent rings" forms a "single ring" or a "condensed ring," the "single ring" or "condensed ring" may form a saturated ring or an unsaturated ring. For example, the ring Q formed in the above general formula (TEMP-104). A and ring Q B are respectively a "single ring" or a "condensed ring." In addition, the ring Q formed in the above general formula (TEMP-105) A and ring Q C is a "condensed ring". The ring Q of the above general formula (TEMP-105) A and ring Q C is ring Q A and ring Q C It becomes a condensed ring through condensation. The ring Q of the above general formula (TMEP-104) A If is a benzene ring, then ring Q A is a single ring. The ring Q of the above general formula (TMEP-104) A If is a naphthalene ring, then ring QA is a condensed ring.
[0824] "Unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic complex ring. "Saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic complex ring.
[0825] As a specific example of an aromatic hydrocarbon ring, a structure in which the group given as a specific example in specific example group G1 is terminated by a hydrogen atom can be cited.
[0826] As a specific example of an aromatic complex ring, a structure in which an aromatic complex ring group is terminated by a hydrogen atom can be cited as a specific example in the specific example group G2.
[0827] As a specific example of an aliphatic hydrocarbon ring, a structure in which the group given as a specific example in the specific example group G6 is terminated by a hydrogen atom can be cited.
[0828] "Forming a ring" means forming a ring with only multiple atoms of the matrix or with multiple atoms of the matrix and one or more additional arbitrary elements. For example, R represented in the above general formula (TEMP-104). 921 and R 922 A ring Q formed by the combination of each other A is, R 921 The carbon atom of the anthracene skeleton that bonds with this, and R 922 It refers to a ring formed by a carbon atom of the anthracene skeleton to which it bonds, and one or more arbitrary elements. As a specific example, R 921 and R 922 Lo ring Q A In the case where it forms, R 921 The carbon atom of the anthracene skeleton that bonds with this, and R 922 In the case where it forms a monocyclic unsaturated ring with four carbon atoms and a carbon atom of the anthracene skeleton to which it bonds, R 921 and R 922 The ring formed by is a benzene ring.
[0829] Here, "any element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur elements, unless otherwise specified in this specification. In the case of any element (e.g., carbon or nitrogen elements), bonds that do not form a ring may be terminated by hydrogen atoms, etc., or substituted by "any substituent" described below. When any element other than carbon is included, the ring formed is a complex ring.
[0830] Unless otherwise specified in this specification, “one or more of any elements” constituting a single ring or a condensed ring are preferably 2 to 15, more preferably 3 to 12, and even more preferably 3 to 5.
[0831] Unless otherwise specified in this specification, among "single ring" and "condensed ring," it is preferably "single ring".
[0832] Unless otherwise specified in this specification, among "saturated ring" and "unsaturated ring," it is preferably "unsaturated ring."
[0833] Unless otherwise stated in this specification, "single ring" is preferably a benzene ring.
[0834] Unless otherwise specified in this specification, the “unsaturated ring” is preferably a benzene ring.
[0835] In cases where “one or more sets of two or more adjacent elements” “combine with one another to form a substituted or unsubstituted ring” or “combine with one another to form a substituted or unsubstituted condensed ring,” unless otherwise specified in this specification, preferably, one or more sets of two or more adjacent elements combine with one another to form a substituted or unsubstituted “unsaturated ring” composed of a plurality of atoms of the matrix and at least one element selected from the group consisting of 1 to 15 carbon elements, nitrogen elements, oxygen elements, and sulfur elements.
[0836] In the case where the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, an "optional substituent" described below. Specific examples of substituents in the case where the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the aforementioned section "Substituents described in this specification."
[0837] In the case where the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, an "optional substituent" described below. Specific examples of substituents in the case where the above-mentioned "mono-ring" or "condensed ring" has a substituent are the substituents described in the aforementioned section "Substituents described in this specification."
[0838] The above is an explanation of the case where “one or more of two or more adjacent groups combine to form a single ring with or without substitution” and the case where “one or more of two or more adjacent groups combine to form a condensed ring with or without substitution” (the case where they combine to form a ring).
[0839] · Substituents in the case of "substituent or non-substituent"
[0840] In one embodiment of this specification, the substituent in the case of "substituted or non-substituted" (which may be referred to as "optional substituent" in this specification) is, for example
[0841] Unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0842] Unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[0843] Unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[0844] Unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[0845] -Si(R 901 )(R 902 )(R 903 ),
[0846] -O-(R 904 ),
[0847] -S-(R 905 ),
[0848] -N(R 906 )(R 907 ),
[0849] Halogen atom, cyano group, nitro group,
[0850] An unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[0851] Unsubstituted complex circulators with 5 to 50 ring-forming atoms
[0852] It is a group selected from the group consisting of, and
[0853] Here, R 901 ~R 907 Each independently
[0854] hydrogen atom,
[0855] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0856] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[0857] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0858] It is a complex circulator with 5 to 50 atoms forming a ring, either substituent or unsubstituent.
[0859] R 901 If there are 2 or more of these, 2 or more R 901 They are identical or different from each other,
[0860] R 902 If there are 2 or more, 2 or more R 902 are identical or different from each other,
[0861] R 903 If there are 2 or more of these, 2 or more R 903 They are identical or different from each other,
[0862] R 904 If there are 2 or more, 2 or more R904 are identical or different from each other,
[0863] R 905 If there are 2 or more, 2 or more R 905 are identical or different from each other,
[0864] R 906 If there are 2 or more of these, 2 or more R 906 They are identical or different from each other,
[0865] R 907 If there are 2 or more of these, 2 or more R 907 They are identical or different from each other.
[0866] In one embodiment, the substituent in the case of "substituted or non-substituted" is,
[0867] alkyl group having 1 to 50 carbon atoms,
[0868] A ring-forming aryl group having 6 to 50 carbon atoms, and
[0869] Complex circulators with 5 to 50 ring-forming atoms
[0870] It is a group selected from the group consisting of
[0871] In one embodiment, the substituent in the case of "substituted or non-substituted" is,
[0872] alkyl group having 1 to 18 carbon atoms,
[0873] A ring-forming aryl group having 6 to 18 carbon atoms, and
[0874] Complex circulators with 5 to 18 ring-forming atoms
[0875] It is a group selected from the group consisting of
[0876] The specific examples of each of the above arbitrary substituents are specific examples of substituents described in the aforementioned section “Substituents described in this specification”.
[0877] Unless otherwise stated in this specification, any adjacent substituents may form a “saturated ring” or an “unsaturated ring,” preferably forming a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, and more preferably forming a benzene ring.
[0878] Unless otherwise stated in this specification, any substituent may have additional substituents. The additional substituents of any substituent are identical to the said arbitrary substituent.
[0879] In the present specification, the numerical range indicated using “AA to BB” means a range that includes the numerical value AA listed before “AA to BB” as a lower limit value and the numerical value BB listed after “AA to BB” as an upper limit value.
[0880] (1st compound)
[0881] An organic EL device according to one embodiment of the present invention has a first light-emitting layer comprising a first compound. The first compound is a compound represented by the following general formula (1A).
[0882] The compound according to the first embodiment described below (compound represented by general formula (12X)), the compound according to the second embodiment (compound represented by general formula (120)), and the compound according to the third embodiment (compound represented by general formulas (1), (2) or (3)) are one embodiment of the compound represented by the following general formula (1A).
[0883] [Tue 32]
[0884]
[0885] (In the above general formula (1A),
[0886] R 101 ~R 110 Each independently
[0887] hydrogen atom,
[0888] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0889] Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
[0890] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[0891] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[0892] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[0893] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[0894] -O-(R 904 The one indicated by ),
[0895] -S-(R 905 The one indicated by ),
[0896] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,
[0897] -C(=O)R 801 The one indicated by,
[0898] -COOR 802 The one indicated by,
[0899] Halogen atoms,
[0900] Cyanogi,
[0901] Nitro,
[0902] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
[0903] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, or
[0904] The above general formula (11) is a device represented by the above general formula,
[0905] However, R 101 ~R 110 At least one of them is a device represented by the above general formula (11), and
[0906] In the case where there are multiple devices represented by the above general formula (11), the multiple devices represented by the above general formula (11) are identical or different from each other,
[0907] L 101 silver
[0908] single bond,
[0909] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[0910] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0911] Ar 101 silver
[0912] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0913] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0914] mx is 0, 1, 2, 3, 4, or 5, and
[0915] L 101 If there are 2 or more of these, 2 or more L 101 They are identical or different from each other,
[0916] Ar 101 If 2 or more exist, 2 or more Ar 101 They are identical or different from each other,
[0917] In the above general formula (11), * indicates the bonding position with the pyrene ring in the above general formula (1A).
[0918] [First embodiment]
[0919] The compound of the first embodiment is a compound represented by the following general formula (12X).
[0920] The compound of the first embodiment (a compound represented by the following general formula (12X)) is one aspect of the first compound (having at least one group represented by the general formula (11) and also represented by the general formula (1A)).
[0921] The compound of the first embodiment is R in the general formula (1A) in the first compound. 101 It is a compound in which the above general formula (11) is combined.
[0922] [Tue 33]
[0923]
[0924] (In the above general formula (12X),
[0925] Py1 and Py2 are each independently
[0926] It is a substituted or unsubstituted 1-pyrenyl group, and
[0927] L1 and L2 are each independently
[0928] A substituted or unsubstituted phenylene group, or
[0929] It is a substituted or unsubstituted naphthylene group, and
[0930] However, where L1 and L2 are each independently substituted or unsubstituted phenylene groups, -L1-L2- in the above general formula (12X) is a group represented by any one of the following general formulas (13-1) to (13-6), (10-1), (20-1) and (30-1), and where L1 and L2 are each independently substituted or unsubstituted naphthylene groups, the bonding position of the naphthylene group as L1 and the bonding position of the naphthylene group as L2 are different, and
[0931] When Py1 and Py2 are each independently a substituted 1-pyrenyl group, the substituent E of the said substituted 1-pyrenyl group is each independently
[0932] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0933] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms,
[0934] - A group represented as Si(Rx)(Ry)(Rz),
[0935] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0936] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0937] In Si(Rx)(Ry)(Rz), Rx, Ry, and Rz are each independently
[0938] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or
[0939] It is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[0940] When there are multiple substituents E, the multiple substituents E are either identical or different from each other.
[0941] (In the case of "substituent or non-substituent" regarding the above substituent E, the substituent F is each independently
[0942] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0943] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms,
[0944] Substituted or unsubstituted phenyl group,
[0945] Substituted or unsubstituted biphenyl group,
[0946] Substituted or unsubstituted terphenyl group,
[0947] Substituted or unsubstituted naphthyl group,
[0948] Substituted or unsubstituted anthryl group,
[0949] Substituted or unsubstituted phenanthryl group,
[0950] Substituted or unsubstituted crisenyl group,
[0951] Substituted or unsubstituted triphenylenyl group,
[0952] Substituted or unsubstituted fluorenyl group,
[0953] Substituted or unsubstituted 9,9'-spirobifluorenyl group,
[0954] Substituted or unsubstituted 9,9-dimethylfluorenyl group,
[0955] It is a substituted or unsubstituted 9,9-diphenylfluorenyl group.
[0956] [Tue 34]
[0957]
[0958] (In the above general formulas (13-1) to (13-6), R 11 ~R 15 and R 11A ~R 15A Each independently
[0959] hydrogen atom,
[0960] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0961] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms,
[0962] - A group represented as Si(Rx)(Ry)(Rz),
[0963] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[0964] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[0965] In Si(Rx)(Ry)(Rz), Rx, Ry, and Rz are each independently
[0966] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or
[0967] It is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[0968] R 11 ~R 15 In the case of "substituted or non-substituted," the substituents are each independently
[0969] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0970] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms,
[0971] Substituted or unsubstituted phenyl group,
[0972] Substituted or unsubstituted biphenyl group,
[0973] Substituted or unsubstituted terphenyl group,
[0974] Substituted or unsubstituted naphthyl group,
[0975] Substituted or unsubstituted anthryl group,
[0976] Substituted or unsubstituted phenanthryl group,
[0977] Substituted or unsubstituted crisenyl group,
[0978] Substituted or unsubstituted triphenylenyl group,
[0979] Substituted or unsubstituted fluorenyl group,
[0980] Substituted or unsubstituted 9,9'-spirobifluorenyl group,
[0981] A substituted or unsubstituted 9,9-dimethylfluorenyl group, or
[0982] It is a substituted or unsubstituted 9,9-diphenylfluorenyl group, and
[0983] R 11 ~R 15 Among the groups consisting of two or more adjacent groups, one or more groups do not combine with each other to form a single ring of substitution or non-substitution, and also do not form a condensed ring of substitution or non-substitution,
[0984] R 11A ~R 15A Among the groups consisting of two or more adjacent groups, one or more groups do not combine with each other to form a single ring of substitution or non-substitution, and also do not form a condensed ring of substitution or non-substitution,
[0985] In the above general formulas (13-1) to (13-6), *1 represents the bonding position with Py1 in the above general formula (12X), and *2 represents the bonding position with Py2 in the above general formula (12X).
[0986] [Tue 35]
[0987]
[0988] (In the above general formula (10-1), R 11 and R 12 of, R 13 and R 14 of, R 21 and R 22 of, R 23 and R 24 One or more of the groups consisting of the
[0989] They combine with each other to form a substituted or unsubstituted single ring,
[0990] They combine with each other to form substituted or unsubstituted condensed rings, or
[0991] Without combining with each other,
[0992] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 11 , R 13 , R 21 and R 23 Each independently
[0993] hydrogen atom,
[0994] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[0995] Substituted or unsubstituted phenyl group,
[0996] Substituted or unsubstituted biphenyl group,
[0997] Substituted or unsubstituted naphthyl group,
[0998] Substituted or unsubstituted phenanthryl group,
[0999] Substituted or unsubstituted fluorenyl group,
[1000] A substituted or unsubstituted 9,9'-spirobifluorenyl group, or
[1001] It is represented by the following general formula (4), and
[1002] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 12 , R14 , R 22 and R 24 Each independently
[1003] hydrogen atom,
[1004] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1005] Substituted or unsubstituted biphenyl group,
[1006] Substituted or unsubstituted naphthyl group,
[1007] Substituted or unsubstituted phenanthryl group,
[1008] Substituted or unsubstituted fluorenyl group,
[1009] A substituted or unsubstituted 9,9'-spirobifluorenyl group, or
[1010] It is represented by the following general formula (4), and
[1011] However, R 11 ~R 14 and R 21 ~R 24 At least one of them is not a hydrogen atom, and
[1012] In the above general formulas (20-1) and (30-1),
[1013] R 31 ~R 33 , R 41 ~R 43 , R 51 ~R 54 and R 61 ~R 64 One or more of the groups consisting of two or more adjacent groups
[1014] They combine with each other to form a substituted or unsubstituted single ring,
[1015] They combine with each other to form substituted or unsubstituted condensed rings, or
[1016] Without combining with each other,
[1017] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 31~R 34 , R 41 ~R 44 , R 51 ~R 54 and R 61 ~R 64 Each independently
[1018] hydrogen atom,
[1019] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1020] Substituted or unsubstituted phenyl group,
[1021] Substituted or unsubstituted biphenyl group,
[1022] Substituted or unsubstituted naphthyl group,
[1023] Substituted or unsubstituted phenanthryl group,
[1024] Substituted or unsubstituted fluorenyl group,
[1025] A substituted or unsubstituted spirobifluorenyl group, or
[1026] It is represented by the following general formula (4), and
[1027] However, R 31 ~R 34 and R 41 ~R 44 At least one of them is not a hydrogen atom, and
[1028] R 51 ~R 54 and R 61 ~R 64 At least one of them is not a hydrogen atom,
[1029] R in the compound represented by the above general formula (10-1). 11 and R 13 The group of, and R 21 and R 23 The keys of are different keys, or R 12 and R 14 The group of, and R 22 and R 24 The groups are different from each other,
[1030] R in the compound represented by the above general formula (20-1) 31 and R 41 These are different from each other, or R 32 and R 42 are different from each other, or R 33 and R 43 These are different from each other, or R 34 and R 44 They are different from each other,
[1031] R in the compound represented by the above general formula (30-1) 51 and R 61 These are different from each other, or R 52 and R 62 are different from each other, or R 53 and R 63 These are different from each other, or R 54 and R 64 They are different from each other,
[1032] In the above general formulas (10-1), (20-1) and (30-1), *1 represents the bonding position with Py1 in the above general formula (12X), and *2 represents the bonding position with Py2 in the above general formula (12X).
[1033] [Tue 36]
[1034]
[1035] (In the above general formula (4), X 13 Silver oxygen atoms, sulfur atoms, or NR 319 And,
[1036] R 311 ~R 318 One or more of the groups consisting of two or more adjacent groups
[1037] They combine with each other to form a substituted or unsubstituted single ring,
[1038] They combine with each other to form substituted or unsubstituted condensed rings, or
[1039] They do not combine with each other,
[1040] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 311 ~R 319 Each independently
[1041] hydrogen atom,
[1042] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1043] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms,
[1044] Substituted or unsubstituted phenyl group,
[1045] Substituted or unsubstituted biphenyl group,
[1046] Substituted or unsubstituted terphenyl group,
[1047] Substituted or unsubstituted naphthyl group,
[1048] Substituted or unsubstituted anthryl group,
[1049] Substituted or unsubstituted phenanthryl group,
[1050] Substituted or unsubstituted crisenyl group,
[1051] Substituted or unsubstituted triphenylenyl group,
[1052] Substituted or unsubstituted fluorenyl group,
[1053] Substituted or unsubstituted 9,9'-spirobifluorenyl group,
[1054] Substituted or unsubstituted 9,9-dimethylfluorenyl group,
[1055] It is a substituted or unsubstituted 9,9-diphenylfluorenyl group, and
[1056] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 311 ~R 319 One of them is R 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R41 ~R 44 , R 51 ~R 54 and R 61 ~R 64 It is a single bond that bonds to at least one of them.)
[1057] (In the above general formulas (10-1), (20-1), (30-1) and the above general formula (4), R 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 , R 61 ~R 64 and R 311 ~R 319 In the case of "substituted or non-substituted," the substituents are each independently
[1058] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1059] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms,
[1060] Substituted or unsubstituted phenyl group,
[1061] Substituted or unsubstituted biphenyl group,
[1062] Substituted or unsubstituted terphenyl group,
[1063] Substituted or unsubstituted naphthyl group,
[1064] Substituted or unsubstituted anthryl group,
[1065] Substituted or unsubstituted phenanthryl group,
[1066] Substituted or unsubstituted crisenyl group,
[1067] Substituted or unsubstituted triphenylenyl group,
[1068] Substituted or unsubstituted fluorenyl group,
[1069] Substituted or unsubstituted 9,9'-spirobifluorenyl group,
[1070] Substituted or unsubstituted 9,9-dimethylfluorenyl group,
[1071] It is a substituted or unsubstituted 9,9-diphenylfluorenyl group.
[1072] Bisspirene bonded through a single linker is known as a host material contained in an emissive layer. However, bisspirene bonded through a single linker is prone to distortion of the molecular structure, is prone to damage to the planarity of the entire compound, and there is a risk of reduced hole transport.
[1073] In this regard, the compound represented by the general formula (12X) according to the first embodiment (hereinafter referred to as the “compound of the first embodiment”) has a structure in which two 1-pyrenyl groups (Py1 and Py2) are bonded through -L1-L2- (two linkers consisting of L1 as a linker and L2 as a linker), and -L1-L2- is an asymmetric structure. It is believed that the compound of the first embodiment has improved hole transportability because, by having such a structure, the molecular structure is not easily twisted, and the planarity of the entire compound is easily maintained.
[1074] Accordingly, according to the compound of the first embodiment, the luminous efficiency can be improved by including the compound in the light-emitting layer.
[1075] The compound of the first embodiment has an asymmetric structure by making -L1-L2- in the general formula (12X) an asymmetric structure, so that the entire compound has an asymmetric structure.
[1076] In the first embodiment, the asymmetric structure of -L1-L2- in the above general formula (12X) means any one of the following embodiments (asymmetric structures 1 to 4).
[1077] · Asymmetric structure 1: L1 and L2 are each independently substituted or unsubstituted phenylene groups, and the bonding position of the phenylene group as L1 and the bonding position of the phenylene group as L2 are different from each other.
[1078] · Asymmetric structure 2: L1 and L2 are each independently substituted or unsubstituted naphthylene groups, and the bonding position of the naphthylene group as L1 and the bonding position of the naphthylene group as L2 are different from each other.
[1079] · Asymmetric structure 3: When one of L1 and L2 is a substituted or unsubstituted phenylene group, and the other of L1 and L2 is a substituted or unsubstituted naphthylene group.
[1080] · Asymmetric structure 4: L1 and L2 are each independently substituted or unsubstituted phenylene groups, and the bonding position of the phenylene group as L1 and the bonding position of the phenylene group as L2 are identical, but the structure of L1 and the structure of L2 are different from each other in terms of the substituents.
[1081] First, asymmetric structures 1 to 3 are explained using compounds represented by the following formulas (130X), (130Y), and (130Z), with carbon positions numbered.
[1082] [Tue 37]
[1083]
[1084] (Asymmetric structure 1)
[1085] As an example of a -L1-L2- asymmetric structure 1, the above general formulas (13-1) to (13-6) can be cited.
[1086] Asymmetric structure 1 is explained using the following general formulas (130-1) to (130-3), which are one mode of the structure represented by the above general formulas (13-1) to (13-3).
[1087] For example, the structure represented by the following general formula (130-1) is asymmetrical because the coupling position of *1 (number 5 in formula (130X)) and the coupling position of *2 (number 6' in formula (130X)) are different from each other.
[1088] The device represented by the following general formula (130-2) has an asymmetric structure because the coupling position of *1 (number 5 in formula (130X)) and the coupling position of *2 (number 4' in formula (130X)) are different from each other.
[1089] The structure represented by the following general formula (130-3) is an asymmetric structure because the coupling position of *1 (number 4 in formula (130X)) and the coupling position of *2 (number 6' in formula (130X)) are different from each other.
[1090] [Tue 38]
[1091]
[1092] (Asymmetric structure 2)
[1093] As an example of -L1-L2- being an asymmetric structure 2, for instance, a group represented by general formulas (13-49) to (13-69) described in the second embodiment described below can be given. An asymmetric structure 2 is described using the following general formulas (130-52) and (130-53), which are one aspect of the group represented by general formulas (13-52) and (13-53) described in the second embodiment.
[1094] For example, the group represented by the following general formula (130-52) has an asymmetric structure in which the bonding position of L1 (naphthylene group) bonded to L2 (number 1 in formula (130Y)) and the bonding position of L2 (naphthylene group) bonded to L1 (number 1' in formula (130Y)) are the same, but the bonding position of *1 (number 4 in formula (130Y)) and the bonding position of *2 (number 5' in formula (130Y)) are different from each other.
[1095] The group represented by the following general formula (130-53) has an asymmetric structure because the bonding position of L1 (naphthylene group) bonded to L2 (number 1 in formula (130Z)) and the bonding position of L2 (naphthylene group) bonded to L1 (number 2' in formula (130Z)) are different from each other.
[1096] [Tue 39]
[1097]
[1098] (Asymmetric structure 3)
[1099] As an example of an asymmetric structure 3, the group represented by general formulas (13-7) to (13-48) described in the second embodiment described below can be cited. All groups represented by general formulas (13-7) to (13-48) are asymmetric structures because the structures of L1 and L2 are different from each other.
[1100] Next, we will explain asymmetric structure 4.
[1101] (Asymmetric structure 4)
[1102] As an example of an asymmetric structure 4, -L1-L2- can be represented by any one of the above general formulas (10-1), (20-1) and (30-1).
[1103] Asymmetric structure 4 is explained using the following general formulas (100-1), (200-1) and (300-1), which are embodiments of the above general formulas (10-1), (20-1) and (30-1).
[1104] For example, the group represented by the following general formula (100-1) has the same bonding position of *1 (number 4 in formula (130X)) and bonding position of *2 (number 4' in formula (130X)), but is different in that the phenylene group as L1 has a substituent (naphthylene group) and the phenylene group as L2 is unsubstituted, so it is an asymmetric structure.
[1105] The group represented by the following general formula (200-1) has the same bonding position of *1 (number 5 in formula (130X)) and bonding position of *2 (number 3' in formula (130X)), but differs in that the phenylene group as L2 has a substituent (phenylene group) and the phenylene group as L1 is unsubstituted, so it is an asymmetric structure.
[1106] The group represented by the following general formula (300-1) has the same bonding position of *1 (number 6 in formula (130X)) and bonding position of *2 (number 6' in formula (130X)), and both the phenylene group as L1 and the phenylene group as L2 have the same substituent (phenylene group), but the bonding position of the phenylene group bonded to the phenylene group of L1 (number 4 in formula (130X)) and the bonding position of the phenylene group bonded to the phenylene group of L2 (number 3 in formula (130X)) are different, so it is an asymmetric structure.
[1107] [Tue 40]
[1108]
[1109]
[1110] In the compound of the first embodiment, the compound represented by the general formula (12X) is preferably a compound represented by the following general formula (120).
[1111] In the compound of the first embodiment, the compound represented by the following general formula (120) has the same meaning as the compound of the second embodiment.
[1112] [Tue 41]
[1113]
[1114] (In the above general formula (120), R 102 ~R 110 A substituted or unsubstituted 1-pyrenyl group having, R 111 ~R 119 The substituted or unsubstituted 1-pyrenyl groups, L1 and L2, having each have independently the same meaning as Py1, Py2, L1 and L2 in the general formula (12X).
[1115] Among the above general formula (120), L1, L2 and R 102 ~R 119 L1, L2, and R in the compound of the second embodiment are each independently 102 ~R119 It has the same meaning as, and the desirable range is also the same.
[1116] Among the above general formulas (120), R in the above general formulas (11) to (13) representing L1 11 ~R 15 , R 21 ~R 27 and R 31 ~R 37 Each independently R in the compound of the second embodiment 11 ~R 15 , R 21 ~R 27 and R 31 ~R 37 It has the same meaning as, and the desirable range is also the same.
[1117] Among the above general formulas (120), R in the above general formulas (11A) to (13A) representing L2 11A ~R 15A , R 21A ~R 27A and R 31A ~R 37A R in the compound of the second embodiment is independently 11A ~R 15A , R 21A ~R 27A and R 31A ~R 37A It has the same meaning as, and the desirable range is also the same.
[1118] In the compound of the first embodiment, the compound represented by the general formula (12X) is preferably a compound represented by the following general formulas (1), (2) or (3).
[1119] [Tue 42]
[1120]
[1121] (In the above general formulas (1) to (3), R 211 ~R 219 A substituted or unsubstituted 1-pyrenyl group having is equivalent to the substituent E of the substituted 1-pyrenyl group in the above general formula (12X), and R111 ~R 119 A substituted or unsubstituted 1-pyrenyl group having is identical in meaning to substituent E of the substituted 1-pyrenyl group in the above general formula (12X), and
[1122] R in the above general formula (1) 11 ~R 14 and R 21 ~R 24 A substituted or unsubstituted biphenylene group having, R in the above general formula (2). 31 ~R 34 and R 41 ~R 44 A substituted or unsubstituted biphenylene group having, and R in the above general formula (3). 51 ~R 54 and R 61 ~R 64 Substituted or unsubstituted biphenylene groups having each independently have the same meaning as -L1-L2- in the general formula (12X).
[1123] Among the above general formulas (1) to (3), R 111 ~R 119 , R 211 ~R 219 , R 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 and R 61 ~R 64 R in the compound of the third embodiment is independently 111 ~R 119 , R 211 ~R 219 , R 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R54 and R 61 ~R 64 It has the same meaning as, and it is desirable that the desirable range is also the same.
[1124] However, among the above general formula (2), R 31 and R 41 These are different from each other, or R 32 and R 42 are different from each other, or R 33 and R 43 These are different from each other, or R 34 and R 44 It is desirable that they are different from each other. Among the above general formula (3), R 51 and R 61 These are different from each other, or R 52 and R 62 are different from each other, or R 53 and R 63 These are different from each other, or R 54 and R 64 They are different from each other.
[1125] (Method for preparing a compound according to the first embodiment)
[1126] The method for preparing the compound according to the first embodiment (the compound represented by the general formula (12X) above) can be prepared by a known method. In addition, the compound according to the first embodiment can also be prepared by using a known alternative reaction and raw materials suited to the target product according to a known method.
[1127] A specific example of the compound according to the first embodiment (a compound represented by the general formula (12X)) is shown in a specific example of the compound of the second embodiment (a compound represented by the general formula (120)) or a specific example of the compound of the third embodiment (a compound represented by the general formulas (1), (2) or (3)).
[1128] [Second embodiment]
[1129] [compound]
[1130] The compound according to the second embodiment is a compound represented by the following general formula (120).
[1131] A compound represented by the following general formula (120) is one embodiment of the first compound (compound represented by the general formula (1A)).
[1132] The compound represented by the following general formula (120) is R in the above general formula (1A). 101 In this case, the above general formula (11) is a compound with a single bond.
[1133] In addition, the compound represented by the following general formula (120) is one aspect of the compound of the first embodiment (the compound represented by the general formula (12X)).
[1134] The compound of the second embodiment has an asymmetric structure as the entire compound is asymmetric, in that -L1-L2- among the following general formula (120) is an asymmetric structure (any one of the aforementioned asymmetric structures 1 to 3).
[1135] [Tuesday 43]
[1136]
[1137] (In the above general formula (120), L1 is represented by any one of the following general formulas (11) to (13), and L2 is represented by any one of the following general formulas (11A) to (13A).
[1138] R 102 ~R 119 Each independently
[1139] hydrogen atom,
[1140] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1141] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms,
[1142] - A group represented as Si(Rx)(Ry)(Rz),
[1143] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1144] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[1145] In Si(Rx)(Ry)(Rz), Rx, Ry, and Rz are each independently
[1146] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or
[1147] It is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[1148] R 102 ~R 119 In the case of "substituted or non-substituted," the substituents are each independently
[1149] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1150] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms,
[1151] Substituted or unsubstituted phenyl group,
[1152] Substituted or unsubstituted biphenyl group,
[1153] Substituted or unsubstituted terphenyl group,
[1154] Substituted or unsubstituted naphthyl group,
[1155] Substituted or unsubstituted anthryl group,
[1156] Substituted or unsubstituted phenanthryl group,
[1157] Substituted or unsubstituted crisenyl group,
[1158] Substituted or unsubstituted triphenylenyl group,
[1159] Substituted or unsubstituted fluorenyl group,
[1160] Substituted or unsubstituted 9,9'-spirobifluorenyl group,
[1161] Substituted or unsubstituted 9,9-dimethylfluorenyl group,
[1162] It is a substituted or unsubstituted 9,9-diphenylfluorenyl group.
[1163] [Tuesday 44]
[1164]
[1165] (In the above general formulas (11) to (13) and (11A) to (13A), R 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A and R 31A ~R 37A Each independently
[1166] hydrogen atom,
[1167] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1168] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1169] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[1170] R 11 ~R 15 , R 21 ~R 27 and R 31 ~R 37 In the case of "substituted or non-substituted," the substituents are each independently
[1171] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1172] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms,
[1173] Substituted or unsubstituted phenyl group,
[1174] Substituted or unsubstituted biphenyl group,
[1175] Substituted or unsubstituted terphenyl group,
[1176] Substituted or unsubstituted naphthyl group,
[1177] Substituted or unsubstituted anthryl group,
[1178] Substituted or unsubstituted phenanthryl group,
[1179] Substituted or unsubstituted crisenyl group,
[1180] Substituted or unsubstituted triphenylenyl group,
[1181] Substituted or unsubstituted fluorenyl group,
[1182] Substituted or unsubstituted 9,9'-spirobifluorenyl group,
[1183] A substituted or unsubstituted 9,9-dimethylfluorenyl group, or
[1184] It is a substituted or unsubstituted 9,9-diphenylfluorenyl group, and
[1185] R 11 ~R 15 Among them, one or more of the groups consisting of two or more adjacent groups do not combine with each other to form a single ring of substitution or non-substitution, and also do not form a condensed ring of substitution or non-substitution, and
[1186] R 11A ~R 15A Among them, one or more of the groups consisting of two or more adjacent groups do not combine with each other to form a single ring of substitution or non-substitution, and also do not form a condensed ring of substitution or non-substitution, and
[1187] R 21 ~R 27 Among them, one or more of the groups consisting of two or more adjacent groups do not combine with each other to form a single ring of substitution or non-substitution, and also do not form a condensed ring of substitution or non-substitution, and
[1188] R 21A ~R 27A Among them, one or more of the groups consisting of two or more adjacent groups do not combine with each other to form a single ring of substitution or non-substitution, and also do not form a condensed ring of substitution or non-substitution, and
[1189] R 31 ~R 37Among them, one or more of the groups consisting of two or more adjacent groups do not combine with each other to form a single ring of substitution or non-substitution, and also do not form a condensed ring of substitution or non-substitution, and
[1190] R 31A ~R 37A Among them, one or more of the groups consisting of two or more adjacent groups do not combine with each other to form a single ring of substitution or non-substitution, and also do not form a condensed ring of substitution or non-substitution, and
[1191] Among the above general formulas (11) to (13) as L1, * indicates the position of combination with *a in the above general formula (120), and R 11 ~R 15 , R 21 ~R 27 and R 31 ~R 37 One of them is a single bond that binds to L2, and
[1192] Among the above general formulas (11A) to (13A) as L2, * indicates the position of combination with *b in the above general formula (120), and R 11A ~R 15A , R 21A ~R 27A and R 31A ~R 37A One of them is a single bond that binds to L1, and
[1193] However, R in L1 12 or R 14 When is a single bond that combines with L2, L2's R 11A , R 13A , R 15A , R 21A ~R 27A and R 31A ~R 37A One of them is a single bond that combines with L1, and
[1194] R in L1 11 or R 15 When is a single bond that combines with L2, L2's R 12A , R13A , R 14A , R 21A ~R 27A and R 31A ~R 37A One of them is a single bond that combines with L1, and
[1195] R in L1 13 When this is a single bond combining with L2, L2's R 11A , R 12A , R 14A , R 15A , R 21A ~R 27A and R 31A ~R 37A One of them is a single bond that combines with L1, and
[1196] R in L1 21 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 22A ~R 27A and R 31A ~R 37A One of them is a single bond that combines with L1, and
[1197] R in L1 22 When is a single bond that combines with L2, L2's R 11A ~R 15A , R 21A , R 23A ~R 27A and R 31A ~R 37A One of them is a single bond that combines with L1, and
[1198] R in L1 23 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 21A ~R 22A , R 24A ~R 27A and R 31A ~R 37A One of them is a single bond that combines with L1, and
[1199] R in L124 When is a single bond that combines with L2, L2's R 11A ~R 15A , R 21A ~R 23A , R 25A ~R 27A and R 31A ~R 37A One of them is a single bond that combines with L1, and
[1200] R in L1 25 When is a single bond that combines with L2, L2's R 11A ~R 15A , R 21A ~R 24A , R 26A ~R 27A and R 31A ~R 37A One of them is a single bond that combines with L1, and
[1201] R in L1 26 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 21A ~R 25A , R 27A and R 31A ~R 37A One of them is a single bond that combines with L1, and
[1202] R in L1 27 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 21A ~R 26A and R 31A ~R 37A One of them is a single bond that combines with L1, and
[1203] R in L1 31 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 21A ~R 27A and R 32A ~R 37A One of them is a single bond that combines with L1, and
[1204] R in L1 32 When is a single bond that combines with L2, L2's R 11A ~R 15A , R 21A ~R 27A , R 31A and R 33A ~R 37A One of them is a single bond that combines with L1, and
[1205] R in L1 33 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 21A ~R 27A , R 31A ~R 32A and R 34A ~R 37A One of them is a single bond that combines with L1, and
[1206] R in L1 34 When is a single bond that combines with L2, L2's R 11A ~R 15A , R 21A ~R 27A , R 31A ~R 33A and R 35A ~R 37A One of them is a single bond that combines with L1, and
[1207] R in L1 35 When is a single bond that combines with L2, L2's R 11A ~R 15A , R 21A ~R 27A , R 31A ~R 34A and R 36A ~R 37A One of them is a single bond that combines with L1, and
[1208] R in L1 36 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 21A ~R27A , R 31A ~R 35A and R 37A One of them is a single bond that combines with L1, and
[1209] R in L1 37 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 21A ~R 27A and R 31A ~R 36A One of them is a single bond that combines with L1.)
[1210] In the compound of the second embodiment, -L1-L2- is preferably represented by any one of the following general formulas (13-1) to (13-69).
[1211] [Tuesday 45]
[1212]
[1213] [Tuesday 46]
[1214]
[1215] [Tue 47]
[1216]
[1217] [Tue 48]
[1218]
[1219] [Tue 49]
[1220]
[1221] [Tue 50]
[1222]
[1223] [Tue 51]
[1224]
[1225] [Tue 52]
[1226]
[1227] [Tuesday 53]
[1228]
[1229] [Tue 54]
[1230]
[1231] (In the above general formulas (13-1) to (13-69), R 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A and R 31A ~R 37A R in the above general formulas (11) to (13) and (11A) to (13A) are each independently 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A and R 31A ~R 37A It has the same meaning as, and in the above general formulas (13-1) to (13-69), *1 indicates the connection position with *a in the above general formula (120), and *2 indicates the connection position with *b in the above general formula (120).
[1232] In the compound of the second embodiment, the compound represented by the general formula (120) is preferably represented by any one of the following general formulas (121) to (131).
[1233] [Tue 55]
[1234]
[1235] [Tuesday 56]
[1236]
[1237] [Tue 57]
[1238]
[1239] [Tue 58]
[1240]
[1241] [Tue 59]
[1242]
[1243] [Tuesday 60]
[1244]
[1245] (In the above general formulas (121) to (131),
[1246] R 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A and R 31A ~R 37A R in the above general formulas (11) to (13) and (11A) to (13A) are each independently 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A and R 31A ~R 37A It has the same meaning as, and R 102 ~R 119 R in the above general formula (120) is independently 102 ~R 119 It has the same meaning as.)
[1247] In the compound of the second embodiment, R 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37 , R 11A ~R 15A , R21A ~R 27A , R 31A ~R 37A and R 102 ~R 119 It is preferable that each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 30 carbon atoms, a group represented by -Si(Rx)(Ry)(Rz), a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 30 carbon atoms. In -Si(Rx)(Ry)(Rz), it is preferable that Rx, Ry, and Rz are each independently an unsubstituted alkyl group having 1 to 30 carbon atoms or an unsubstituted ring-forming aryl group having 6 to 30 carbon atoms.
[1248] In the compound of the second embodiment, R 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A , R 31A ~R 37A and R 102 ~R 119 It is more preferable that each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 18 carbon atoms, a group represented by -Si(Rx)(Ry)(Rz), a substituted or unsubstituted ring-forming aryl group having 6 to 18 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 18 carbon atoms. It is more preferable that Rx, Ry, and Rz in -Si(Rx)(Ry)(Rz) are each independently an unsubstituted alkyl group having 1 to 18 carbon atoms or an unsubstituted ring-forming aryl group having 6 to 18 carbon atoms.
[1249] In the compound of the second embodiment, R 11 ~R 15 , R 21~R 27 , R 31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A , R 31A ~R 37A and R 102 ~R 119 Each independently a hydrogen atom, a substituted or unsubstituted C1–18 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinazolinyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted phenanthrolinyl group, substituted or unsubstituted 1-carbazolyl group, substituted or unsubstituted 2-carbazolyl group, substituted or unsubstituted 3-carbazolyl group, substituted or unsubstituted 4-carbazolyl group, substituted or unsubstituted 9-carbazolyl group, substituted or unsubstituted benzocarbazolyl group, substituted or unsubstituted azacarbazolyl group, substituted or unsubstituted dizacarbazolyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted naphthobenzofuranyl group, substituted or unsubstituted azadibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted It is preferable that it be a naphthobenzothiophenyl group, a substituted or unsubstituted azadibenzothiophenyl group, or a substituted or unsubstituted diazadibenzothiophenyl group.
[1250] In the compound of the second embodiment, R 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A and R 31A ~R 37A and R 102 ~R 119 It is preferable that each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group.
[1251] In the compound of the second embodiment, R 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A , and R 31A ~R 37A , and R 102 ~R 119 It is more preferable that each is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthyl group, a substituted or unsubstituted fluorenyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothiophenyl group, an unsubstituted 9,9-dimethylfluorenyl group, or an unsubstituted 9,9-diphenylfluorenyl group.
[1252] In the compound of the second embodiment, R 11 ~R 15 , R 21 ~R 27 , R31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A and R 31A ~R 37A It is preferable that it be a hydrogen atom.
[1253] In the compound of the second embodiment, R 102 ~R 119 It is preferable that it be a hydrogen atom.
[1254] In the compound of the second embodiment, R 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A , R 31A ~R 37A and R 102 ~R 119 In the case of "substituted or unsubstituted," the substituents are each preferably independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group.
[1255] In the compound of the second embodiment, R 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A , R 31A ~R 37A and R 102 ~R119 In the case of "substituted or unsubstituted," it is more preferable that the substituents are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 18 carbon atoms, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthyl group, a substituted or unsubstituted fluorenyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothiophenyl group, an unsubstituted 9,9-dimethylfluorenyl group, or an unsubstituted 9,9-diphenylfluorenyl group.
[1256] According to the compound of the second embodiment, the luminous efficiency can be improved by incorporating the compound into the light-emitting layer.
[1257] (Method for preparing a compound according to the second embodiment)
[1258] The method for manufacturing the compound according to the second embodiment (the compound represented by the general formula (120) above) can be manufactured by a known method. Additionally, the compound according to the second embodiment can also be manufactured by using a known alternative reaction and raw materials suited to the target object according to a known method.
[1259] Specific examples of the compound according to the second embodiment (compound represented by the general formula (120) above) include, for instance, the following compounds. However, the present invention is not limited to these specific examples.
[1260] [Tuesday 61]
[1261]
[1262] [Tuesday 62]
[1263]
[1264] [Tuesday 63]
[1265]
[1266] [Tuesday 64]
[1267]
[1268] [Tuesday 65]
[1269]
[1270] [Tuesday 66]
[1271]
[1272] [Tuesday 67]
[1273]
[1274] [Tuesday 68]
[1275]
[1276] [Tuesday 69]
[1277]
[1278] [Tue 70]
[1279]
[1280] [Tue 71]
[1281]
[1282] [Tue 72]
[1283]
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[1299]
[1300] [Tue 81]
[1301]
[1302] [Tue 82]
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[1304] [Tue 83]
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[1306] [Tue 84]
[1307]
[1308] [Tue 85]
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[1310] [Tue 86]
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[1312] [Tue 87]
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[1314] [Tue 88]
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[1320] [Tue 91]
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[1322] [Tue 92]
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[1324] [Tue 93]
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[1327]
[1328] [Tue 95]
[1329]
[1330] [Tue 96]
[1331]
[1332] [Tue 97]
[1333]
[1334] [Tue 98]
[1335]
[1336] [Tue 99]
[1337]
[1338] [Third Embodiment]
[1339] [compound]
[1340] The compound according to the third embodiment is a compound represented by the following general formula (1), (2) or (3).
[1341] A compound according to the third embodiment (a compound represented by the following general formulas (1), (2) or (3)) is an embodiment of the first compound (a compound having at least one group represented by the general formula (11) and also represented by the general formula (1A)).
[1342] The compound according to the third embodiment is R in the general formula (1A) of the first compound. 101 In this case, the above general formula (11) is a compound with a single bond.
[1343] Additionally, a compound represented by the following general formulas (1), (2) or (3) is one aspect of the compound of the first embodiment (a compound represented by the general formula (12X)).
[1344] The compound of the third embodiment has an asymmetric structure in which the linker connecting two 1-pyrenyl groups among the following general formulas (1), (2), or (3) has an asymmetric structure (the asymmetric structure 4 described above).
[1345] [Tue 100]
[1346]
[1347] (In the above general formulas (1) to (3),
[1348] R 111 ~R 119 and R 211 ~R 219 Each independently
[1349] hydrogen atom,
[1350] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1351] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms,
[1352] - A group represented as Si(Rx)(Ry)(Rz),
[1353] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1354] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[1355] In Si(Rx)(Ry)(Rz), Rx, Ry, and Rz are each independently
[1356] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or
[1357] It is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[1358] In the above general formula (1),
[1359] R 11 and R 12 of, R 13 and R 14 of, R 21 and R 22 of, R 23and R 24 One or more of the groups consisting of the
[1360] They combine with each other to form a substituted or unsubstituted single ring,
[1361] They combine with each other to form substituted or unsubstituted condensed rings, or
[1362] Without combining with each other,
[1363] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 11 , R 13 , R 21 and R 23 Each independently
[1364] hydrogen atom,
[1365] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1366] Substituted or unsubstituted phenyl group,
[1367] Substituted or unsubstituted biphenyl group,
[1368] Substituted or unsubstituted naphthyl group,
[1369] Substituted or unsubstituted phenanthryl group,
[1370] Substituted or unsubstituted fluorenyl group,
[1371] A substituted or unsubstituted 9,9'-spirobifluorenyl group, or
[1372] It is represented by the following general formula (4), and
[1373] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 12 , R 14 , R 22 and R 24 Each independently
[1374] hydrogen atom,
[1375] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1376] Substituted or unsubstituted biphenyl group,
[1377] Substituted or unsubstituted naphthyl group,
[1378] Substituted or unsubstituted phenanthryl group,
[1379] Substituted or unsubstituted fluorenyl group,
[1380] A substituted or unsubstituted 9,9'-spirobifluorenyl group, or
[1381] It is represented by the following general formula (4), and
[1382] However, R 11 ~R 14 and R 21 ~R 24 At least one of them is not a hydrogen atom,
[1383] In the above general formulas (2) to (3),
[1384] R 31 ~R 33 , R 41 ~R 43 , R 51 ~R 54 and R 61 ~R 64 One or more of the groups consisting of two or more adjacent groups
[1385] They combine with each other to form a substituted or unsubstituted single ring,
[1386] They combine with each other to form substituted or unsubstituted condensed rings, or
[1387] Without combining with each other,
[1388] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 and R 61 ~R 64 Each independently
[1389] hydrogen atom,
[1390] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1391] Substituted or unsubstituted phenyl group,
[1392] Substituted or unsubstituted biphenyl group,
[1393] Substituted or unsubstituted naphthyl group,
[1394] Substituted or unsubstituted phenanthryl group,
[1395] Substituted or unsubstituted fluorenyl group,
[1396] A substituted or unsubstituted spirobifluorenyl group, or
[1397] It is represented by the following general formula (4), and
[1398] However, R 31 ~R 34 and R 41 ~R 44 At least one of them is not a hydrogen atom,
[1399] R 51 ~R 54 and R 61 ~R 64 At least one of them is not a hydrogen atom, and
[1400] R in the compound represented by the above general formula (1) 11 and R 13 The group of, and R 21 and R 23 The keys of are different keys, or R 12 and R 14 The group of, and R 22 and R 24 The groups are different from each other,
[1401] R in the compound represented by the above general formula (2) 31 and R 41 The group of, and R 32 and R 42 of, R 33 and R 43 The group of, and R 34 and R 44Among the groups, at least one group is different from each other,
[1402] R in the compound represented by the above general formula (3) 51 and R 61 The group of, and R 52 and R 62 of, R 53 and R 63 , and R 54 and R 64 At least one of the groups is different from the others.)
[1403] [Tue 101]
[1404]
[1405] (In the above general formula (4), X 13 Silver oxygen atoms, sulfur atoms, or NR 319 is,
[1406] R 311 ~R 318 One or more of the groups consisting of two or more adjacent groups
[1407] They combine with each other to form a substituted or unsubstituted single ring,
[1408] They combine with each other to form substituted or unsubstituted condensed rings, or
[1409] Without combining with each other,
[1410] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 311 ~R 319 Each independently
[1411] hydrogen atom,
[1412] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1413] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms,
[1414] Substituted or unsubstituted phenyl group,
[1415] Substituted or unsubstituted biphenyl group,
[1416] Substituted or unsubstituted terphenyl group,
[1417] Substituted or unsubstituted naphthyl group,
[1418] Substituted or unsubstituted anthryl group,
[1419] Substituted or unsubstituted phenanthryl group,
[1420] Substituted or unsubstituted crisenyl group,
[1421] Substituted or unsubstituted triphenylenyl group,
[1422] Substituted or unsubstituted fluorenyl group,
[1423] Substituted or unsubstituted 9,9'-spirobifluorenyl group,
[1424] Substituted or unsubstituted 9,9-dimethylfluorenyl group,
[1425] It is a substituted or unsubstituted 9,9-diphenylfluorenyl group, and
[1426] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 311 ~R 319 One of them is R 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 and R 61 ~R 64 It is a single bond that bonds to at least one of them.)
[1427] (In the above general formulas (1) to (3), R 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 , R61 ~R 64 , R 111 ~R 119 , R 211 ~R 219 and R 311 ~R 319 In the case of "substituted or non-substituted," the substituents are each independently
[1428] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1429] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms,
[1430] Substituted or unsubstituted phenyl group,
[1431] Substituted or unsubstituted biphenyl group,
[1432] Substituted or unsubstituted terphenyl group,
[1433] Substituted or unsubstituted naphthyl group,
[1434] Substituted or unsubstituted anthryl group,
[1435] Substituted or unsubstituted phenanthryl group,
[1436] Substituted or unsubstituted crisenyl group,
[1437] Substituted or unsubstituted triphenylenyl group,
[1438] Substituted or unsubstituted fluorenyl group,
[1439] Substituted or unsubstituted 9,9'-spirobifluorenyl group,
[1440] Substituted or unsubstituted 9,9-dimethylfluorenyl group,
[1441] It is a substituted or unsubstituted 9,9-diphenylfluorenyl group.
[1442] [Tue 102]
[1443]
[1444] Among the above general formula (1), R 11 ~R 14The phenylene group having corresponds to L1 in the general formula (12X) of the first embodiment, and R 21 ~R 24 The phenylene group having [it] corresponds to L2 in the general formula (12X) of the first embodiment.
[1445] Therefore, in the above general formula (1), the linker connecting the two 1-pyrenyl groups is said to have an asymmetric structure, which is the case of the aforementioned asymmetric structure 4, where the phenylene group (R) as L1 11 ~R 14 The bonding position of the phenylene group having ) and the phenylene group as L2 (R 21 ~R 34 The bonding positions of the phenylene group having ) are identical at the para positions, but L1(R 11 ~R 14 The structure of the phenylene group having ) and L2(R 21 ~R 34 It refers to cases where the structure of the phenylene group having is different from each other, including substituents.
[1446] In the above general formula (1), as an embodiment in which the linker connecting the two 1-pyrenyl groups has an asymmetric structure, for example, "R 11 and R 13 The group of, and R 21 and R 23 The keys of are different keys, or R 12 and R 14 The group of, and R 22 and R 24 One example is a mode in which the parts of the group are different from each other.
[1447] In the above general formula (1), "R 11 and R 13 The group of, and R 21 and R 23 The case where the compositions are different from each other is explained as an example. The following general formulas (1a), (1b), and (1c) represent substructures of the above general formula (1).
[1448] [Tue 103]
[1449]
[1450] (among the above general formulas (1a), (1b) and (1c),
[1451] R 12 , R 14 , R 22 and R 24 Each is independently R in the above general formula (1). 12 , R 14 , R 22 and R 24 It has the same meaning as
[1452] *a1 represents the position of combination with *11 in the above general formula (1), and
[1453] *a2 represents the position of combination with *12 in the above general formula (1).
[1454] For example, R 11 This is "A", and R 13 In the case of this "B",
[1455] R 11 and R 13 The group of, and R 21 and R 23 Saying that the group of is the same group means,
[1456] R 21 This is "A", and R 23 This is “B” (general formula (1a) above), or R 21 This is "B", and R 23 This refers to the case where "A" is used (general formula (1b) above).
[1457] However, "A" and "B" are different from each other.
[1458] Also, R 11 and R 13 In the case where this is simultaneously "A",
[1459] R 11 and R 13 The group of, and R 21 and R 23 Saying that the group of is the same group means,
[1460] R21 and R 23 This refers to the case where "A" is present at the same time (the above general formula (1c)).
[1461] That is, R 11 and R 13 The group of, and R 21 and R 23 Saying that the keys of are different from each other means, for example, R 11 This is "A", and R 13 This is "B", and
[1462] R 21 and R 23 At the same time, it is either "A" or,
[1463] R 21 and R 23 This is simultaneously "B" or or
[1464] R 21 and R 23 There is a case where at least one of them is “C” which is different from “A” and “B”, and
[1465] Also, R 11 and R 13 This is simultaneously "A", and
[1466] R 21 and R 23 If at least one of them is "B",
[1467] R 21 and R 23 Examples include cases where at least one of them is a “C” that is different from “A”.
[1468] In the above general formula (1), "R 12 and R 14 The group of, and R 22 and R 24 The same applies to "the groups of are different from each other."
[1469] [Tue 104]
[1470]
[1471] Among the above general formula (2), R 31 ~R 34The phenylene group having corresponds to L1 in the general formula (12X) of the first embodiment, and R 41 ~R 44 The phenylene group having [it] corresponds to L2 in the general formula (12X) of the first embodiment.
[1472] Therefore, in the above general formula (2), the linker connecting the two 1-pyrenyl groups is said to have an asymmetric structure, which is the case of the aforementioned asymmetric structure 4, and the phenylene group (R) as L1 31 ~R 34 The bonding position of the phenylene group having ) and the phenylene group as L2 (R 41 ~R 44 The bonding positions of the phenylene group having ) are identical at the meta positions, but L1(R 31 ~R 34 The structure of the phenylene group having ) and L2(R 41 ~R 44 It refers to cases where the structure of the phenylene group having is different from each other, including substituents.
[1473] Specifically, the statement that the linker connecting two 1-pyrenyl groups has an asymmetric structure is, R 31 and R 41 These are different from each other or R 32 and R 42 are different from each other, or R 33 and R 43 These are different from each other, or R 34 and R 44 It means cases where they are different from each other.
[1474] In the above general formula (2), as an embodiment in which the linker connecting the two 1-pyrenyl groups has an asymmetric structure, for example, "R 31 and R 41 The group of, and R 32 and R 42 of, R 33 and R 43 The group of, and R 34 and R 44 Among the parts of the group, at least one part may be different from the others.
[1475] In the above general formula (2), "R 31 and R 41 The group of, and R 32 and R 42 of, R 33 and R 43 The group of, and R 34 and R 44 Regarding “at least one of the groups is different from each other,” “R 31 and R 41 The group of, and R 32 and R 42 The case where the compositions are different from each other is explained as an example. The following general formulas (2a), (2b), and (2c) represent the partial structures of the above general formula (2).
[1476] [Tue 105]
[1477]
[1478] (among the above general formulas (2a), (2b) and (2c),
[1479] R 33 , R 34 , R 43 and R 44 Each independently R in the above general formula (2) 33 , R 34 , R 43 and R 44 It has the same meaning as
[1480] *b1 represents the position of combination with *21 in the above general formula (2), and
[1481] *b2 indicates the position of combination with *22 in the above general formula (2).
[1482] For example, R 31 This is "A", and R 41 In the case of this "B" clause,
[1483] R 31 and R 41 The group of, and R 32 and R 42 Saying that the group of is the same group means,
[1484] R 32 ga is "A" and R 42 If it is “B” (the above general formula (2a)), or
[1485] R 32 ga is 「B」 and R 42 This refers to the case where is “A” (the above general formula (2b)).
[1486] However, "A" and "B" are different from each other.
[1487] Also, R 31 and R 41 In the case where this is simultaneously "A",
[1488] R 31 and R 41 The group of, and R 32 and R 42 Saying that the group of is the same group means,
[1489] R 32 and R 42 This refers to the case where it is simultaneously “A” (the above general formula (2c)).
[1490] That is, R 31 and R 41 The group of, and R 32 and R 42 Saying that the keys of are different from each other means, for example, R 31 This is "A", and R 41 This is "B", and
[1491] R 32 and R 42 If it is simultaneously "A",
[1492] R 32 and R 42 is simultaneously "B", or
[1493] R 32 and R 42 There is a case where at least one of them is “C” which is different from “A” and “B”, and
[1494] Also, R 31 and R 41 This is simultaneously "A", and
[1495] R 32 and R 42 If at least one of them is "B",
[1496] R 32 and R 42 Examples include cases where at least one of them is a “C” that is different from “A”.
[1497] In the above general formula (2), "R 31 and R 41 The group of, and R 33 and R 43 The same applies to "the clauses of are different from each other," and "R 31 and R 41 The group of, and R 34 and R 44 The same applies to "the groups of are different from each other."
[1498] [Tue 106]
[1499]
[1500] Among the above general formula (3), R 51 ~R 54 The phenylene group having corresponds to L1 in the general formula (12X) of the first embodiment, and R 61 ~R 64 The phenylene group having [it] corresponds to L2 in the general formula (12X) of the first embodiment.
[1501] Therefore, in the above general formula (3), the linker connecting the two 1-pyrenyl groups is said to have an asymmetric structure, which is the case of the aforementioned asymmetric structure 4, and the phenylene group (R) as L1 51 ~R 54 The bonding position of the phenylene group having ) and the phenylene group as L2 (R 61 ~R 64 The bonding positions of the phenylene group having ) are identical at the ortho positions, but L1(R 51 ~R 54 The structure of the phenylene group having ) and L2(R 61 ~R 64It refers to cases where the structure of the phenylene group having is different from each other, including substituents.
[1502] Specifically, the statement that the linker connecting two 1-pyrenyl groups has an asymmetric structure is, R 51 and R 61 These are different from each other, or R 52 and R 62 are different from each other, or R 53 and R 63 These are different from each other, or R 54 and R 64 It means cases where they are different from each other.
[1503] In the above general formula (2), as an embodiment in which the linker connecting the two 1-pyrenyl groups has an asymmetric structure, for example, "R 51 and R 61 The group of, and R 52 and R 62 of, R 53 and R 63 , and R 54 and R 64 Among the parts of the group, at least one part may be different from the others.
[1504] In the above general formula (3), "R 51 and R 61 The group of, and R 52 and R 62 of, R 53 and R 63 , and R 54 and R 64 Regarding “at least one of the groups is different from each other,” “R 51 and R 61 The group of, and R 52 and R 62 The case where the groups are different from each other is explained as an example. The following general formulas (3a), (3b), and (3c) represent the partial structures of the above general formula (3).
[1505] [Tue 107]
[1506]
[1507] (Among the above general formulas (3a), (3b) and (3c),
[1508] R 53 , R 54 , R 63 and R 64 Each independently R in the above general formula (3) 53 , R 54 , R 63 and R 64 It has the same meaning as
[1509] *c1 represents the position of combination with *31 in the above general formula (3), and
[1510] *c2 represents the position of combination with *32 in the above general formula (3).
[1511] For example, R 51 This is "A", and R 61 In the case of this "B" clause,
[1512] R 51 and R 61 The group of, and R 52 and R 62 Saying that the group of is the same group means,
[1513] R 52 ga is "A" and R 62 If it is “B” (the above general formula (3a)), or
[1514] R 52 ga is 「B」 and R 62 This refers to the case where is “A” (the above general formula (3b)).
[1515] However, "A" and "B" are different from each other.
[1516] Also, R 51 and R 61 If this is simultaneously "A", R 51 and R 61 The group of, and R 52 and R 62 Saying that the group of is the same group means,
[1517] R 52 and R 62This refers to the case where the group is simultaneously “A” (the above general formula (3c)).
[1518] That is, R 51 and R 61 Joe, R 52 and R 62 Saying that the keys of are different from each other means, for example, R 51 This is "A", and R 61 This is "B", and
[1519] R 52 and R 62 If it is simultaneously "A",
[1520] R 52 and R 62 is simultaneously "B", or
[1521] R 52 and R 62 There is a case where at least one of them is “C” which is different from “A” and “B”, and
[1522] Also, R 51 and R 61 This is simultaneously "A", and
[1523] R 52 and R 62 If at least one of them is "B",
[1524] R 52 and R 62 Examples include cases where at least one of them is a “C” that is different from “A”.
[1525] In the above general formula (3), "R 51 and R 61 The group of, and R 53 and R 63 The same applies to "the clauses of are different from each other," and "R 51 and R 61 The group of, and R 54 and R 64 The same applies to "the groups of are different from each other."
[1526] In the compound of the third embodiment, R 111 ~R 119 and R211 ~R 219 It is preferable that each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 18 carbon atoms, a group represented by -Si(Rx)(Ry)(Rz), a substituted or unsubstituted ring-forming aryl group having 6 to 18 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 18 carbon atoms. In -Si(Rx)(Ry)(Rz), it is preferable that Rx, Ry, and Rz are each independently an unsubstituted alkyl group having 1 to 18 carbon atoms or an unsubstituted ring-forming aryl group having 6 to 18 carbon atoms.
[1527] In the compound of the third embodiment, R 111 ~R 119 and R 211 ~R 219 It is preferable that each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group.
[1528] In the compound of the third embodiment, R 111 ~R 119 and R 211 ~R 219 It is preferable that it be a hydrogen atom.
[1529] In the compound of the third embodiment, R 11 and R 12 of, R 13 and R 14 of, R 21 and R 22 of, R 23 and R 24 One or more groups consisting of the groups of do not combine with each other, and R 31 ~R 33 , R41 ~R 43 , R 51 ~R 54 and R 61 ~R 64 It is desirable that at least one of the groups consisting of two or more adjacent groups does not combine with each other.
[1530] The compound of the third embodiment is preferably represented by the following general formula (1-1), (2-1) or (3-1).
[1531] [Tuesday 108]
[1532]
[1533] (In the above general formulas (1-1), (2-1) and (3-1), R 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 , R 61 ~R 64 R in the above general formulas (1) to (3) is independently 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 , R 61 ~R 64 It has the same meaning as.)
[1534] In the compound of the third embodiment, R 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 and R 61 ~R 64Each is independently a hydrogen atom, a substituted or unsubstituted C1-C8 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and
[1535] However, R 12 , R 14 , R 22 and R 24 It is preferable that it is not a substituted or unsubstituted phenyl group.
[1536] In the compound of the third embodiment, R 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 and R 61 ~R 64 Each is independently a hydrogen atom, an unsubstituted C1-C8 alkyl group, an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthyl group, a substituted or unsubstituted fluorenyl group, an unsubstituted 9,9'-spirobifluorenyl group, an unsubstituted 9,9-dimethylfluorenyl group, an unsubstituted 9,9-diphenylfluorenyl group, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothiophenyl group, and
[1537] However, R 12 , R 14 , R 22 and R 24 It is more preferable that it is not a substituted or unsubstituted phenyl group.
[1538] In the compound of the third embodiment, R 11 and R 12of, R 13 and R 14 of, R 21 and R 22 of, R 23 and R 24 One or more groups of groups consisting of the groups combine with each other to form a single ring with or without substitution, or a condensed ring with or without substitution, and
[1539] R 31 ~R 33 , R 41 ~R 43 , R 51 ~R 54 and R 61 ~R 64 It is desirable that at least one of the groups consisting of two or more adjacent groups combines to form a substituted or non-substituted single ring or a substituted or non-substituted condensed ring.
[1540] In the compound of the third embodiment, R 11 and R 12 of, R 13 and R 14 of, R 21 and R 22 of, R 23 and R 24 It is also desirable that the groups formed by the group do not combine with each other.
[1541] That is, in the compound of the third embodiment, R 11 and R 12 The groups of do not combine with each other, and R 13 and R 14 The groups of do not combine with each other, and R 21 and R 22 The groups of do not combine with each other, and also R 23 and R 24 It is also desirable that the groups of [them] do not combine with each other.
[1542] In the compound of the third embodiment, R 31 ~R 33 , R 41 ~R 43 , R 51 ~R54 and R 61 ~R 64 It is also desirable that groups consisting of two or more adjacent groups do not combine with each other.
[1543] The compound of the third embodiment is preferably represented by any one of the following general formulas (1-2), (2-2) to (2-3) and (3-2) to (3-4).
[1544] [Tuesday 109]
[1545]
[1546] [Tue 110]
[1547]
[1548] (In the above general formulas (1-2), (2-2) to (2-3) and (3-2) to (3-4), R 13 ~R 14 , R 21 ~R 22 , R 31 , R 33 , R 34 , R 41 , R 43 , R 44 , R 51 ~R 54 and R 61 ~R 64 R in the above general formulas (1) to (3) is independently 13 ~R 14 , R 21 ~R 22 , R 31 , R 33 , R 34 , R 41 , R 43 , R 44 , R 51 ~R 54 and R 61 ~R 64 It has the same meaning as, and R 301 ~R 308 Each is independently R in the above general formulas (1) to (3). 11 ~R 14 , R 21 ~R24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 and R 61 ~R 64 It has the same meaning as.)
[1549] In the above general formulas (1-2), (2-2) to (2-3) and (3-2) to (3-4), R 13 ~R 14 , R 21 ~R 22 , R 31 , R 33 , R 34 , R 41 , R 43 , R 44 , R 51 ~R 54 , R 61 ~R 64 and R 301 ~R 308 Each is independently a hydrogen atom, a substituted or unsubstituted C1-C8 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and
[1550] However, R 14 and R 22 It is preferable that it is not a substituted or unsubstituted phenyl group.
[1551] In the above general formulas (1-2), (2-2) to (2-3) and (3-2) to (3-4), R 13 ~R 14 , R 21 ~R 22 , R 31 , R 33 , R 34 , R41 , R 43 , R 44 , R 51 ~R 54 , R 61 ~R 64 and R 301 ~R 308 Each is independently a hydrogen atom, an unsubstituted C1-C8 alkyl group, an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthyl group, a substituted or unsubstituted fluorenyl group, an unsubstituted 9,9'-spirobifluorenyl group, an unsubstituted 9,9-dimethylfluorenyl group, an unsubstituted 9,9-diphenylfluorenyl group, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothiophenyl group, and
[1552] However, R 14 and R 22 It is preferable that it is not a substituted or unsubstituted phenyl group.
[1553] In the compound of the third embodiment, R 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 , R 61 ~R 64 , R 111 ~R 119 , R 211 ~R 219 and R 301 ~R 308 In the case of "substituted or unsubstituted," the substituents are each preferably independently a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group.
[1554] In the compound of the third embodiment, R 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 , R 61 ~R 64 , R 111 ~R 119 , R 211 ~R 219 and R 301 ~R 308 In the case of "substituted or unsubstituted," the substituents are preferably each independently an unsubstituted alkyl group having 1 to 8 carbon atoms, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthyl group, a substituted or unsubstituted fluorenyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothiophenyl group, an unsubstituted 9,9-dimethylfluorenyl group, or an unsubstituted 9,9-diphenylfluorenyl group.
[1555] According to the compound of the third embodiment, the luminous efficiency can be improved by incorporating the compound into the light-emitting layer.
[1556] (Method for preparing a compound according to the third embodiment)
[1557] The method for manufacturing the compound according to the third embodiment (the compound represented by the general formulas (1), (2), or (3) above) can be manufactured by a known method. Additionally, the compound according to the third embodiment can also be manufactured by using known alternative reactions and raw materials suited to the target object according to a known method.
[1558] Specific examples of the compound according to the third embodiment (a compound represented by the above general formulas (1), (2) or (3)) include, for instance, the following compounds. However, the present invention is not limited to these specific examples.
[1559] [Tue 111]
[1560]
[1561] [Tue 112]
[1562]
[1563] [Tue 113]
[1564]
[1565] [Tue 114]
[1566]
[1567] [Tue 115]
[1568]
[1569] [Tuesday 116]
[1570]
[1571] [Tue 117]
[1572]
[1573] [Tuesday 118]
[1574]
[1575] [Tue 119]
[1576]
[1577] [Fourth embodiment]
[1578] [Materials for Organic EL Devices]
[1579] The organic EL device material according to the fourth embodiment includes a compound according to the first embodiment (a compound represented by the general formula (12X)), a compound according to the second embodiment (a compound represented by the general formula (120)), or a compound according to the third embodiment (at least one of the compounds represented by any one of the general formulas (1) to (3)).
[1580] According to the fourth embodiment, a material for an organic EL device capable of improving luminous efficiency can be obtained.
[1581] In addition, the organic EL device material according to the fourth embodiment may further contain other compounds. If the organic EL device material according to the fourth embodiment further contains other compounds, the other compounds may be solid or liquid.
[1582] [Fifth embodiment]
[1583] [Organic EL Device]
[1584] Hereinafter, the configuration of an organic EL device according to the fifth embodiment will be described.
[1585] An organic EL device according to the fifth embodiment includes an anode, a cathode, and a light-emitting layer included between the anode and the cathode.
[1586] The light-emitting layer comprises a compound according to the first embodiment (a compound represented by the general formula (12X)), a compound according to the second embodiment (a compound represented by the general formula (120)), or a compound according to the third embodiment (at least one of the compounds represented by any one of the general formulas (1) to (3)).
[1587] The light-emitting layer preferably contains a compound according to the first embodiment, a compound according to the second embodiment, or a compound according to the third embodiment as a host material.
[1588] In the present specification, "host material" refers to a material that is included, for example, "50 mass% or more of the layer." Accordingly, for example, the light-emitting layer contains 50 mass% or more of the total mass of the light-emitting layer, the compound according to the first embodiment, the compound according to the second embodiment, or the compound according to the third embodiment.
[1589] (Emission wavelength of organic EL devices)
[1590] The organic EL device according to the fifth embodiment preferably emits light with a main peak wavelength of 430 nm or more and 480 nm or less when the device is driven.
[1591] The main peak wavelength of light emitted by an organic EL device during device operation is measured as follows. The spectral radiance luminance spectrum when a voltage is applied to the organic EL device such that the current density is 10 mA / cm² is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta). In the obtained spectral radiance luminance spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is measured, and this is set as the main peak wavelength (unit: nm).
[1592] The organic EL device according to the fifth embodiment may have one or more organic layers in addition to the light-emitting layer. As for the organic layer, for example, at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole barrier layer, and an electron barrier layer may be provided. In addition, the light-emitting layer may have two or more layers.
[1593] In the organic EL device according to the fifth embodiment, the organic layer may be composed only of a light-emitting layer, but may additionally have at least one layer selected from the group consisting of, for example, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole barrier layer, and an electron barrier layer.
[1594] In the organic EL device according to the fifth embodiment, it is preferable to have a hole transport layer between the anode and the light-emitting layer.
[1595] In the organic EL device according to the fifth embodiment, it is preferable to have an electron transport layer between the anode and the light-emitting layer.
[1596] FIG. 1 shows a schematic configuration of an example of an organic EL device according to the fifth embodiment.
[1597] The organic EL element (1) includes a transparent substrate (2), an anode (3), a cathode (4), and an organic layer (10) disposed between the anode (3) and the cathode (4). The organic layer (10) is configured such that a hole injection layer (6), a hole transport layer (7), a light-emitting layer (5), an electron transport layer (8), and an electron injection layer (9) are stacked in this order, starting from the anode (3) side.
[1598] (Fluorescent compounds)
[1599] In the organic EL device (1) according to the fifth embodiment, the light-emitting layer (5) preferably further comprises a fluorescent light-emitting compound (hereinafter also referred to as “compound M1”).
[1600] In the organic EL element (1) according to the fifth embodiment, the fluorescent emitting compound (compound M1) is preferably one or more compounds selected from the group consisting of the compound represented by the following general formula (100), the compound represented by the following general formula (3), the compound represented by the following general formula (4), the compound represented by the following general formula (5), the compound represented by the following general formula (6), the compound represented by the following general formula (7), the compound represented by the following general formula (8), the compound represented by the following general formula (9), and the compound represented by the following general formula (10).
[1601] (Compound represented by general formula (100))
[1602] A compound represented by the general formula (100) is described.
[1603] [Tue 120]
[1604]
[1605] (of general formula (100),
[1606] R 11 ~R 16 A group consisting of two or more adjacent elements, R 17 ~R 20 A group consisting of two or more adjacent elements, Ra1 ~R a5 A group consisting of two or more adjacent members, and R a6 ~R a10 Among the groups consisting of two or more adjacent groups, at least one group combines with each other to form a single ring with 3 to 30 substituted or non-substituted ring-forming atoms, or forms a condensed ring with 3 to 30 substituted or non-substituted ring-forming atoms, or does not combine with each other.
[1607] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 11 ~R 20 , R a1 ~R a5 and R a6 ~R a10 Each independently
[1608] hydrogen atom,
[1609] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,
[1610] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 30 carbon atoms,
[1611] Substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms,
[1612] Substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms,
[1613] Substituted or unsubstituted amino group,
[1614] Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,
[1615] Complex circulators with 5 to 30 substituent or unsubstituent ring-forming atoms,
[1616] Substituted or unsubstituted alkenyl groups having 2 to 30 carbon atoms,
[1617] Substituted or unsubstituted ring-forming aryloxy groups with 6 to 30 carbon atoms,
[1618] Substituted or unsubstituted ring-forming arylthio groups with 6 to 30 carbon atoms,
[1619] Substituted or unsubstituted phosphanyl group,
[1620] Substituted or unsubstituted phosphoryl group,
[1621] Substituted or unsubstituted silyl group,
[1622] Substituted or unsubstituted ring-forming aryl carbonyl groups having 6 to 30 carbon atoms,
[1623] Cyano group, nitro group, carboxyl group, or
[1624] It is a halogen atom.)
[1625] "R 11 ~R 16 A group consisting of two or more adjacent elements, R 17 ~R 20 A group consisting of two or more adjacent elements, R a1 ~R a5 A group consisting of two or more adjacent members, and R a6 ~R a10 A specific example is described in which one or more of the groups consisting of two or more adjacent groups combine to form a single ring or condensed ring having 3 to 30 substituted or non-substituted ring-forming atoms.
[1626] As a specific example in which two or more adjacent groups combine to form a condensation ring, R in the general formula (100) above 17 ~R 20 For example, a compound represented by the following general formula (10A) can be cited. In the compound represented by the following general formula (10A), adjacent R 18 and R 19 and R 20 Three of them combine with each other to form a condensed ring.
[1627] [Tue 121]
[1628]
[1629] (of general formula (10A), R a1 ~R a10and R 11 ~R 17 Each is independently R in the above general formula (100). a1 ~R a10 and R 11 ~R 17 It has the same meaning as.)
[1630] In addition, as a specific example in which two or more adjacent groups are combined to form a ring, R in the above formula (100) 11 ~R 16 For example, a compound represented by the following general formula (10B) can be cited. In the compound represented by the following general formula (10B), R 12 and R 13 and R 14 and R 15 The two sets of rings combine to form two separate rings.
[1631] [Tue 122]
[1632]
[1633] (of general formula (10B), R a1 ~R a10 , R 11 and R 16 ~R 20 Each is independently R in the above general formula (100). a1 ~R a10 , R 11 and R 16 ~R 20 It has the same meaning as.)
[1634] In one embodiment, the compound represented by the above general formula (100) is a compound represented by the following general formula (10-1).
[1635] [Tue 123]
[1636]
[1637] (In the above general formula (10-1), R 11 ~R 12 , R 14 ~R 20and R a1 ~R a10 Each is independently R in the above general formula (100). 11 ~R 12 , R 14 ~R 20 and R a1 ~R a10 It has the same meaning as,
[1638] n 10 is 0, 1, 2, or 3, and
[1639] L 100 It is a substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming divalent complex circulating group having 5 to 50 atoms, and
[1640] n 10 When this is 2, multiple L 100 They are identical or different from each other,
[1641] n 10 When this is 3, multiple L 100 They are identical or different from each other,
[1642] Ar 100 It is a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, a substituted or unsubstituted ring-forming heterocyclic group with 5 to 50 atoms, a cyano group, or a substituted silyl group.
[1643] In the above general formula (10-1), n 10 It is preferable that it be 0, 1, or 2.
[1644] In the above general formula (10-1), L 100 silver
[1645] It is a single bond, or
[1646] Substituted or unsubstituted phenyl group,
[1647] Substituted or unsubstituted biphenyl group,
[1648] Substituted or unsubstituted terphenyl group,
[1649] Substituted or unsubstituted naphthyl group,
[1650] Substituted or unsubstituted anthryl group,
[1651] Substituted or unsubstituted phenanthryl group,
[1652] Substituted or unsubstituted fluorenyl group,
[1653] Substituted or unsubstituted 9,9'-spirobifluorenyl group,
[1654] Substituted or unsubstituted 9,9-dimethylfluorenyl group,
[1655] Substituted or unsubstituted 9,9-diphenylfluorenyl group,
[1656] Substituted or unsubstituted dibenzofuranyl group,
[1657] Substituted or unsubstituted naphthobenzofuranyl group,
[1658] Substituted or unsubstituted dibenzothiophenyl groups, and
[1659] It is preferable that it be a divalent group derived by removing one hydrogen atom from any one group selected from the group consisting of substituted or unsubstituted naphthobenzothiophenyl groups.
[1660] In the above general formula (10-1), Ar 100 silver
[1661] Cyanogi,
[1662] Substituted silyl group,
[1663] Substituted or unsubstituted phenyl group,
[1664] Substituted or unsubstituted biphenyl group,
[1665] Substituted or unsubstituted terphenyl group,
[1666] Substituted or unsubstituted naphthyl group,
[1667] Substituted or unsubstituted anthryl group,
[1668] Substituted or unsubstituted phenanthryl group,
[1669] Substituted or unsubstituted fluorenyl group,
[1670] Substituted or unsubstituted 9,9'-spirobifluorenyl group,
[1671] Substituted or unsubstituted 9,9-dimethylfluorenyl group,
[1672] Substituted or unsubstituted 9,9-diphenylfluorenyl group,
[1673] Substituted or unsubstituted dibenzofuranyl group,
[1674] Substituted or unsubstituted naphthobenzofuranyl group,
[1675] A substituted or unsubstituted dibenzothiophenyl group, or
[1676] It is preferable that it be a substituted or unsubstituted naphthobenzothiophenyl group.
[1677] In the above general formula (10-1),
[1678] R 11 ~R 12 , R 14 ~R 16 and R 17 ~R 20 A group consisting of two or more adjacent elements, R a1 ~R a5 A group consisting of two or more adjacent elements, and R a6 ~R a10 Among the groups consisting of two or more adjacent groups, at least one group combines with each other to form a single ring with 3 to 30 substituted or non-substituted ring-forming atoms, or forms a condensed ring with 3 to 30 substituted or non-substituted ring-forming atoms, or does not combine with each other.
[1679] In one embodiment, R in the general formula (100) 12 and R 13 These combine with each other to form a single ring with 3 to 30 substituted or unsubstituted ring-forming atoms, or a condensed ring with 3 to 30 substituted or unsubstituted ring-forming atoms.
[1680] In one embodiment, the compound represented by the general formula (100) above is a compound represented by the following formula (10-2).
[1681] [Tue 124]
[1682]
[1683] (In general formula (10-2), Xc is an oxygen atom, a sulfur atom, or CR c1 R c2 is, R 11 , R 14 ~R 20 , R a1 ~R a10 and R c3 ~R c8 Each is independently R in the above general formula (100). 11 ~R 20 It has the same meaning as,
[1684] R c1 and R c2 Each independently
[1685] hydrogen atom,
[1686] Unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1687] Unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[1688] Unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[1689] Unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1690] -Si(R 901 )(R 902 )(R 903 ),
[1691] -O-(R 904 ),
[1692] -S-(R 905 ),
[1693] -N(R 906 )(R 907 ),
[1694] Halogen atom, cyano group, nitro group,
[1695] An unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or
[1696] It is a monovalent complex circulator with 5 to 50 ring-forming atoms in an unsubstituted ring.
[1697] R 901 ~R 907 Each independently
[1698] hydrogen atom,
[1699] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1700] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1701] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1702] It is a monovalent complex circulator with 5 to 50 atoms forming a ring, either substituent or nonsubstituent.
[1703] R 901 If this plural exists, the plural R 901 They are identical or different from each other. R 902 If there are multiple instances of R 902 are identical or different from each other. R 903 If this plural exists, the plural R 903 They are identical or different from each other. R 904 If there are multiple instances of R 904 are identical or different from each other. R 905 If there are multiple instances of R 905 are identical or different from each other. R 906 If this plural exists, the plural R 906 They are identical or different from each other.
[1704] R 907 If this plural exists, the plural R 907 They are identical or different from each other.
[1705] In the above general formula (10-2),
[1706] R 14 ~R 16 and R 17 ~R20 A group consisting of two or more adjacent elements, R a1 ~R a5 A group consisting of two or more adjacent elements, R a6 ~R a10 A group consisting of two or more adjacent elements, R c3 ~R c8 A group consisting of two or more adjacent elements, and R c1 and R c2 At least one of the groups combines with one another to form a single ring with 3 to 30 substituted or unsubstituted ring-forming atoms, or a condensed ring with 3 to 30 substituted or unsubstituted ring-forming atoms, or does not combine with one another.
[1707] In one embodiment, R in the general formula (100) 18 ~R 20 Two or more of them combine to form a single ring with 3 to 30 substituted or unsubstituted ring-forming atoms, or a condensed ring with 3 to 30 substituted or unsubstituted ring-forming atoms.
[1708] In one embodiment, the compound represented by the above general formula (100) is a compound represented by the following general formula (10-3).
[1709] [Tue 125]
[1710]
[1711] (of the general formula (10-3), R 11 ~R 17 , R a1 ~R a10 and R d1 ~R d7 Each is independently R in the above general formula (100). 11 ~R 20 It has the same meaning as.)
[1712] In the above general formula (10-3),
[1713] R 11 ~R 16A group consisting of two or more adjacent elements, R 17 and R d1 ~R d7 A group consisting of two or more adjacent elements, R a1 ~R a5 A group consisting of two or more adjacent elements, and R a6 ~R a10 Among the groups consisting of two or more adjacent groups, at least one group combines with each other to form a single ring with 3 to 30 substituted or non-substituted ring-forming atoms, or forms a condensed ring with 3 to 30 substituted or non-substituted ring-forming atoms, or does not combine with each other.
[1714] In one embodiment, R that does not participate in ring formation in the general formulas (100) and (10-1) to (10-3) 11 ~R 20 , R a1 ~R a5 , R a6 ~R a10 , R c1 ~R c8 and R d1 ~R d7 These each independently
[1715] hydrogen atom,
[1716] An unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or
[1717] It is a monovalent complex circulator with 5 to 50 ring-forming atoms in an unsubstituted ring.
[1718] As for the compound represented by the above general formula (100), for example, the compound shown below can be cited as a specific example.
[1719] [Tuesday 126]
[1720]
[1721] [Tue 127]
[1722]
[1723] [Tuesday 128]
[1724]
[1725] [Tue 129]
[1726]
[1727] [Tue 130]
[1728]
[1729] [Tue 131]
[1730]
[1731] [Tue 132]
[1732]
[1733] (Compound represented by general formula (3))
[1734] A compound represented by the general formula (3) is described.
[1735] [Tue 133]
[1736]
[1737] (In the above general formula (3),
[1738] R 301 ~R 310 One or more of the groups consisting of two or more adjacent groups
[1739] They combine with each other to form a substituted or unsubstituted single ring,
[1740] They combine with each other to form substituted or unsubstituted condensed rings, or
[1741] Without combining with each other,
[1742] R 301 ~R 310 At least one of them is a univalent element represented by the following general formula (31), and
[1743] R that does not form the above-mentioned single ring, does not form the above-mentioned condensed ring, and is not a monovalent group represented by the following general formula (31). 301 ~R 310 Each independently
[1744] hydrogen atom,
[1745] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1746] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[1747] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[1748] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1749] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[1750] -O-(R 904 The one indicated by ),
[1751] -S-(R 905 The one indicated by ),
[1752] -N(R 906 )(R 907 The one indicated by ),
[1753] Halogen atoms,
[1754] Cyanogi,
[1755] Nitro,
[1756] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1757] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[1758] [Tue 134]
[1759]
[1760] (In the above general formula (31),
[1761] Ar 301 and Ar 302 Each independently
[1762] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1763] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[1764] L 301 ~L 303 Each independently
[1765] single bond,
[1766] Substituted or unsubstituted ring-forming arylene groups having 6 to 30 carbon atoms, or
[1767] It is a divalent complex circulator with 5 to 30 substituent or unsubstituent ring-forming atoms, and
[1768] * indicates the bonding position in the pyrene ring in the above general formula (3).
[1769] Among the fluorescently emitting compounds (compound M1), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 Each independently
[1770] hydrogen atom,
[1771] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1772] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1773] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1774] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[1775] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or
[1776] It is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[1777] R 901 If this plural exists, the plural R 901 They are identical or different from each other,
[1778] R 902If there are multiple instances of R 902 are identical or different from each other,
[1779] R 903 If this plural exists, the plural R 903 They are identical or different from each other,
[1780] R 904 If there are multiple instances of R 904 are identical or different from each other,
[1781] R 905 If there are multiple instances of R 905 are identical or different from each other,
[1782] R 906 If this plural exists, the plural R 906 They are identical or different from each other,
[1783] R 907 If this plural exists, the plural R 907 They are identical or different from each other.
[1784] In the above general formula (3), R 301 ~R 310 It is preferable that two of them are represented by the above general formula (31).
[1785] In one embodiment, the compound represented by the above general formula (3) is a compound represented by the following general formula (33).
[1786] [Tue 135]
[1787]
[1788] (In the above general formula (33),
[1789] R 311 ~R 318 Each is independently a non-univalent group R represented by the general formula (31) in the general formula (3) above. 301 ~R 310 It has the same meaning as,
[1790] L311 ~L 316 Each independently
[1791] single bond,
[1792] Substituted or unsubstituted ring-forming arylene groups having 6 to 30 carbon atoms, or
[1793] It is a divalent complex circulator with 5 to 30 substituent or unsubstituent ring-forming atoms, and
[1794] Ar 312 , Ar 313 , Ar 315 and Ar 316 Each independently
[1795] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1796] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[1797] In the above general formula (31), L 301 It is preferable that it be a single bond, and L 302 and L 303 It is preferable that it be a single bond.
[1798] In one embodiment, the compound represented by the above general formula (3) is represented by the following general formula (34) or general formula (35).
[1799] [Tue 136]
[1800]
[1801] (In the above general formula (34),
[1802] R 311 ~R 318 Each is independently a non-univalent group R represented by the general formula (31) in the general formula (3) above. 301 ~R 310 It has the same meaning as,
[1803] L 312 , L 313 , L 315 and L 316Each is independently L in the above general formula (33). 312 , L 313 , L 315 and L 316 It has the same meaning as,
[1804] Ar 312 , Ar 313 , Ar 315 and Ar 316 Each is independently Ar in the above general formula (33). 312 , Ar 313 , Ar 315 and Ar 316 It has the same meaning as.)
[1805] [Tue 137]
[1806]
[1807] (In the above general formula (35),
[1808] R 311 ~R 318 Each is independently a non-univalent group R represented by the general formula (31) in the general formula (3) above. 301 ~R 310 It has the same meaning as,
[1809] Ar 312 , Ar 313 , Ar 315 and Ar 316 Each is independently Ar in the above general formula (33). 312 , Ar 313 , Ar 315 and Ar 316 It has the same meaning as.)
[1810] In the above general formula (31), preferably, Ar 301 and Ar 302 At least one of them is represented by the following general formula (36).
[1811] In the above general formulas (33) to (35), preferably Ar 312 and Ar 313At least one of them is represented by the following general formula (36).
[1812] In the above general formulas (33) to (35), preferably Ar 315 and Ar 316 At least one of them is represented by the following general formula (36).
[1813] [Tue 138]
[1814]
[1815] (In the above general formula (36),
[1816] X3 represents an oxygen atom or a sulfur atom,
[1817] R 321 ~R 327 One or more of the groups consisting of two or more adjacent groups
[1818] They combine with each other to form a substituted or unsubstituted single ring,
[1819] They combine with each other to form substituted or unsubstituted condensed rings, or
[1820] They do not combine with each other,
[1821] R that does not form the above-mentioned single ring and also does not form the above-mentioned condensed ring 321 ~R 327 Each independently
[1822] hydrogen atom,
[1823] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1824] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[1825] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[1826] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1827] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[1828] -O-(R 904 The one indicated by ),
[1829] -S-(R 905 The one indicated by ),
[1830] -N(R 906 )(R 907 The one indicated by ),
[1831] Halogen atoms,
[1832] Cyanogi,
[1833] Nitro,
[1834] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1835] It is a complex circulating ring with 5 to 50 substituent or unsubstituent atoms, and
[1836] * is L 302 , L 303 , L 312 , L 313 , L 315 or L 316 Indicates the bonding position with.)
[1837] It is preferable that X3 be an oxygen atom.
[1838] R 321 ~R 327 At least one of them,
[1839] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1840] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[1841] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[1842] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1843] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1844] It is preferable that the complex circulator has 5 to 50 ring-forming atoms, whether substituent or non-substituent.
[1845] In the above general formula (31), Ar 301 This is a group represented by the above general formula (36), and Ar 302 It is preferable that the group be a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.
[1846] In the above general formulas (33) to (35), Ar 312 is a group represented by the above general formula (36), and Ar 313 It is preferable that this be a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.
[1847] In the above general formulas (33) to (35), Ar 315 is a group represented by the above general formula (36), and Ar 316 It is preferable that this be a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.
[1848] In one embodiment, the compound represented by the above general formula (3) is represented by the following general formula (37).
[1849] [Tue 139]
[1850]
[1851] (In the above general formula (37),
[1852] R 311 ~R 318 Each is independently a non-univalent group R represented by the general formula (31) in the general formula (3) above. 301 ~R 310 It has the same meaning as,
[1853] R 321 ~R 327 One or more of the groups consisting of two or more adjacent groups
[1854] They combine with each other to form a substituted or unsubstituted single ring,
[1855] They combine with each other to form substituted or unsubstituted condensed rings, or
[1856] Without combining with each other,
[1857] R 341 ~R 347 One or more of the groups consisting of two or more adjacent groups
[1858] They combine with each other to form a substituted or unsubstituted single ring,
[1859] They combine with each other to form substituted or unsubstituted condensed rings, or
[1860] They do not combine with each other,
[1861] R that does not form the above-mentioned single ring and also does not form the above-mentioned condensed ring 321 ~R 327 And R 341 ~R 347 Each independently
[1862] hydrogen atom,
[1863] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1864] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[1865] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[1866] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1867] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[1868] -O-(R 904 The one indicated by ),
[1869] -S-(R 905 The one indicated by ),
[1870] -N(R 906 )(R 907 The one indicated by ),
[1871] Halogen atoms,
[1872] Cyanogi,
[1873] Nitro,
[1874] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1875] It is a complex circulating ring with 5 to 50 substituent or unsubstituent atoms, and
[1876] R 331 ~R 335 And R 351 ~R 355 Each independently
[1877] hydrogen atom,
[1878] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1879] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[1880] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[1881] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1882] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[1883] -O-(R 904 The one indicated by ),
[1884] -S-(R 905 The one indicated by ),
[1885] -N(R 906 )(R 907 The one indicated by ),
[1886] Halogen atom, cyano group, nitro group,
[1887] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1888] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[1889] As for the compound represented by the above general formula (3), for example, the compounds shown below can be cited as specific examples.
[1890] [Tue 140]
[1891]
[1892] [Tue 141]
[1893]
[1894] [Tue 142]
[1895]
[1896] [Tue 143]
[1897]
[1898] [Tue 144]
[1899]
[1900] [Tue 145]
[1901]
[1902] [Tue 146]
[1903]
[1904] [Tue 147]
[1905]
[1906] [Tue 148]
[1907]
[1908] [Tue 149]
[1909]
[1910] [Tue 150]
[1911]
[1912] (Compound represented by general formula (4))
[1913] A compound represented by the general formula (4) is described.
[1914] [Tue 151]
[1915]
[1916] (In the above general formula (4),
[1917] Z is independently either a CRa or a nitrogen atom, and
[1918] Ring A1 and Ring A2 are each independently
[1919] Substituted or unsubstituted ring-forming aromatic hydrocarbon rings having 6 to 50 carbon atoms, or
[1920] It is a complex ring with 5 to 50 substituent or unsubstituent atoms forming a ring, and
[1921] In the case where multiple Ras exist, one or more of a set consisting of two or more adjacent Ras among the multiple Ras
[1922] They combine with each other to form a substituted or unsubstituted single ring,
[1923] They combine with each other to form substituted or unsubstituted condensed rings, or
[1924] Without combining with each other,
[1925] n21 and n22 are each independently 0, 1, 2, 3, or 4, and
[1926] In the case where multiple Rb exist, one or more of a group consisting of two or more adjacent Rb among the multiple Rb
[1927] They combine with each other to form a substituted or unsubstituted single ring,
[1928] They combine with each other to form substituted or unsubstituted condensed rings, or
[1929] Without combining with each other,
[1930] In the case where multiple Rc exist, one or more of a group consisting of two or more adjacent Rc
[1931] They combine with each other to form a substituted or unsubstituted single ring,
[1932] They combine with each other to form substituted or unsubstituted condensed rings, or
[1933] They do not combine with each other,
[1934] Ra, Rb, and Rc, which do not form the above-mentioned single ring and also do not form the above-mentioned condensation ring, are each independently
[1935] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1936] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[1937] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[1938] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1939] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[1940] -O-(R 904 The one indicated by ),
[1941] -S-(R 905 The one indicated by ),
[1942] -N(R 906 )(R 907 The one indicated by ),
[1943] Halogen atoms,
[1944] Cyanogi,
[1945] Nitro,
[1946] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1947] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[1948] The "aromatic hydrocarbon ring" of the A1 and A2 rings has the same structure as the compound in which a hydrogen atom is introduced into the aforementioned "aryl group."
[1949] The “aromatic hydrocarbon ring” of the A1 ring and A2 ring includes two carbon atoms on the condensed 2-ring structure in the center of the general formula (4) as ring-forming atoms.
[1950] Specific examples of “substituted or unsubstituted ring-forming aromatic hydrocarbons having 6 to 50 carbon atoms” include compounds in which a hydrogen atom is introduced into the “aryl group” described in Specific Example Group G1.
[1951] The "complex ring" of the A1 and A2 rings has the same structure as the compound in which a hydrogen atom is introduced into the aforementioned "complex ring."
[1952] The “complex ring” of the A1 ring and A2 ring includes two carbon atoms on the condensed 2-ring structure in the center of the general formula (4) as ring-forming atoms.
[1953] Specific examples of “a complex ring having 5 to 50 substituent or non-substituent ring-forming atoms” include compounds in which a hydrogen atom is introduced into the “complex ring group” described in Specific Example Group G2.
[1954] Rb is bonded to any one of the carbon atoms forming an aromatic hydrocarbon ring as an A1 ring, or to any one of the atoms forming a heterocyclic ring as an A1 ring.
[1955] Rc is bonded to any one of the carbon atoms forming an aromatic hydrocarbon ring as an A2 ring, or to any one of the atoms forming a heterocyclic ring as an A2 ring.
[1956] It is preferable that at least one of Ra, Rb and Rc is represented by the following general formula (4a), and it is more preferable that at least two are represented by the following general formula (4a).
[1957] [Tue 152]
[1958]
[1959] (In the above general formula (4a),
[1960] L 401 silver
[1961] single bond,
[1962] Substituted or unsubstituted ring-forming arylene groups having 6 to 30 carbon atoms, or
[1963] It is a divalent complex circulator with 5 to 30 substituent or unsubstituent ring-forming atoms, and
[1964] Ar 401 silver
[1965] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
[1966] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, or
[1967] It is represented by the following general formula (4b).
[1968] [Tue 153]
[1969]
[1970] (In the above general formula (4b),
[1971] L 402 and L 403 Each independently
[1972] single bond,
[1973] Substituted or unsubstituted ring-forming arylene groups having 6 to 30 carbon atoms, or
[1974] It is a divalent complex circulator with 5 to 30 substituent or unsubstituent ring-forming atoms, and
[1975] Ar 402 and Ar 403 A group consisting of
[1976] They combine with each other to form a substituted or unsubstituted single ring,
[1977] They combine with each other to form substituted or unsubstituted condensed rings, or
[1978] Without combining with each other,
[1979] Ar that does not form the above-mentioned single ring and also does not form the above-mentioned condensed ring 402 and Ar 403 Each independently
[1980] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[1981] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[1982] In one embodiment, the compound represented by the above general formula (4) is represented by the following general formula (42).
[1983] [Tue 154]
[1984]
[1985] (In the above general formula (42),
[1986] R 401 ~R 411 One or more of the groups consisting of two or more adjacent groups
[1987] They combine with each other to form a substituted or unsubstituted single ring,
[1988] They combine with each other to form substituted or unsubstituted condensed rings, or
[1989] Without combining with each other,
[1990] R that does not form the above-mentioned single ring and also does not form the above-mentioned condensed ring 401 ~R 411 Each independently
[1991] hydrogen atom,
[1992] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1993] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[1994] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[1995] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[1996] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[1997] -O-(R 904 The one indicated by ),
[1998] -S-(R905 The one indicated by ),
[1999] -N(R 906 )(R 907 The one indicated by ),
[2000] Halogen atoms,
[2001] Cyanogi,
[2002] Nitro,
[2003] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2004] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[2005] R 401 ~R 411 It is preferable that at least one of them is represented by the above general formula (4a), and it is more preferable that at least two are represented by the above general formula (4a).
[2006] R 404 and R 411 It is preferable that this be represented by the above general formula (4a).
[2007] In one embodiment, the compound represented by the general formula (4) is a compound in which a structure represented by the following general formula (4-1) or general formula (4-2) is bonded to the A1 ring.
[2008] In addition, in one embodiment, the compound represented by the general formula (42) is R 404 ~R 407 This is a compound in which a structure represented by the following general formula (4-1) or general formula (4-2) is bonded to the bonding ring.
[2009] [Tue 155]
[2010]
[2011] (In the above general formula (4-1), the two * each independently bonds to a ring-forming carbon atom of an aromatic hydrocarbon ring or a ring-forming atom of a heterocyclic ring as the A1 ring of the above general formula (4), or R of the above general formula (42) 404 ~R 407 Combine with any one of them,
[2012] The three *s of the above general formula (4-2) each independently bond to a ring-forming carbon atom of an aromatic hydrocarbon ring or a ring-forming atom of a heterocyclic ring as the A1 ring of the above general formula (4), or to R of the above general formula (42). 404 ~R 407 Combines with any one of them,
[2013] R 421 ~R 427 One or more of the groups consisting of two or more adjacent groups
[2014] They combine with each other to form a substituted or unsubstituted single ring,
[2015] They combine with each other to form substituted or unsubstituted condensed rings, or
[2016] Without combining with each other,
[2017] R 431 ~R 438 One or more of the groups consisting of two or more adjacent groups
[2018] They combine with each other to form a substituted or unsubstituted single ring,
[2019] They combine with each other to form substituted or unsubstituted condensed rings, or
[2020] They do not combine with each other,
[2021] R that does not form the above-mentioned single ring and also does not form the above-mentioned condensed ring 421 ~R 427 And R 431 ~R 438 Each independently
[2022] hydrogen atom,
[2023] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2024] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2025] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2026] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2027] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[2028] -O-(R 904 The one indicated by ),
[2029] -S-(R 905 The one indicated by ),
[2030] -N(R 906 )(R 907 The one indicated by ),
[2031] Halogen atoms,
[2032] Cyanogi,
[2033] Nitro,
[2034] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2035] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[2036] In one embodiment, the compound represented by the above general formula (4) is a compound represented by the following general formula (41-3), general formula (41-4), or general formula (41-5).
[2037] [Tuesday 156]
[2038]
[2039] [Tue 157]
[2040]
[2041] [Tue 158]
[2042]
[2043] (among the above general formulas (41-3), (41-4) and (41-5),
[2044] The A1 ring is as defined in the above general formula (4), and
[2045] R 421 ~R 427 Each is independently R in the above general formula (4-1). 421 ~R 427 It has the same meaning as,
[2046] R 440 ~R 448 Each independently R in the above general formula (42) 401 ~R 411 It has the same meaning as.)
[2047] In one embodiment, the ring-forming aromatic hydrocarbon ring having 6 to 50 carbon atoms, which is substituted or unsubstituted as the A1 ring of the general formula (41-5), is,
[2048] Substituted or unsubstituted naphthalene rings, or
[2049] It is a substituted or unsubstituted fluorene ring.
[2050] In one embodiment, the complex ring having 5 to 50 substituted or unsubstituted ring-forming atoms as the A1 ring of the general formula (41-5) is,
[2051] Substituted or unsubstituted dibenzofuran ring,
[2052] Substituted or unsubstituted carbazole rings, or
[2053] It is a substituted or unsubstituted dibenzothiophen ring.
[2054] In one embodiment, the compound represented by the above general formula (4) or the above general formula (42) is selected from the group consisting of compounds represented by the following general formulas (461) to (467).
[2055] [Tue 159]
[2056]
[2057] [Tue 160]
[2058]
[2059] [Tue 161]
[2060]
[2061] [Tue 162]
[2062]
[2063] [Tue 163]
[2064]
[2065] (among the above general formulas (461), general formula (462), general formula (463), general formula (464), general formula (465), general formula (466) and general formula (467),
[2066] R 421 ~R 427 Each is independently R in the above general formula (4-1). 421 ~R 427 It has the same meaning as,
[2067] R 431 ~R 438 Each is independently R in the above general formula (4-2). 431 ~R 438 It has the same meaning as,
[2068] R 440 ~R 448 And R 451 ~R 454 Each independently R in the above general formula (42) 401 ~R 411 It has the same meaning as,
[2069] X4 is an oxygen atom, NR 801 , or C(R 802 )(R 803 ) and,
[2070] R 801 , R 802 and R 803 Each independently
[2071] hydrogen atom,
[2072] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2073] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2074] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2075] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[2076] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or
[2077] It is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[2078] R 801 If this plural exists, the plural R 801 They are identical or different from each other,
[2079] R 802 If there are multiple instances of R 802 are identical or different from each other,
[2080] R 803 If this plural exists, the plural R 803 They are identical or different from each other.
[2081] In one embodiment, the compound represented by the general formula (42) is R 401 ~R 411 One or more of the sets of two or more adjacent sets combine to form a substituted or non-substituted ring, or combine to form a substituted or non-substituted condensed ring, and the embodiments thereof are described in detail below as compounds represented by the general formula (45).
[2082] (Compound represented by general formula (45))
[2083] A compound represented by the general formula (45) is described.
[2084] [Tue 164]
[2085]
[2086] (In the above general formula (45),
[2087] R 461 and R 462 A group consisting of, R 462 and R 463 A group consisting of, R 464 and R 465 A group consisting of, R 465 and R 466 A group consisting of, R 466 and R 467 A group consisting of, R 468 and R 469 A group consisting of, R 469 and R 470 A group consisting of, and, R 470 and R 471 Two or more of the groups selected from a group consisting of groups formed by combine with each other to form a substituent or nonsubstituent monoring or a substituent or nonsubstituent condensed ring, and
[2088] step,
[2089] R 461 and R 462 A group and R consisting of 462 and R 463 A composition consisting of;
[2090] R 464 and R 465 A group and R consisting of 465 and R 466 A composition consisting of;
[2091] R 465 and R 466 Groups and R consisting of 466 and R 467 A group consisting of;
[2092] R 468 and R 469 A group and R consisting of 469 and R 470 A group consisting of; and
[2093] R 469 and R 470 Groups and R consisting of 470 and R 471 A group consisting of such elements does not simultaneously form a ring, and
[2094] R 461 ~R 471 The two or more rings formed by this are identical or different from each other,
[2095] R that does not form the above-mentioned single ring and also does not form the above-mentioned condensed ring 461 ~R 471 Each independently
[2096] hydrogen atom,
[2097] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2098] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2099] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2100] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2101] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[2102] -O-(R 904 The one indicated by ),
[2103] -S-(R 905 ), -N(R 906 )(R 907 The one indicated by ),
[2104] Halogen atoms,
[2105] Cyanogi,
[2106] Nitro,
[2107] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2108] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[2109] In the above general formula (45), R n and R n+1 (n represents an integer selected from 461, 462, 464–466, and 468–470) combine with each other to form R n and R n+1 Together with the two ring-forming carbon atoms that bond, it forms a substituted or unsubstituted single ring or a substituted or unsubstituted condensed ring. The ring is preferably composed of atoms selected from the group consisting of carbon atoms, oxygen atoms, sulfur atoms, and nitrogen atoms, and the number of atoms in the ring is preferably 3 to 7, and more preferably 5 or 6.
[2110] The number of ring structures in the compound represented by the general formula (45) is, for example, 2, 3, or 4. Each of the two or more ring structures may exist on the same benzene ring on the matrix of the general formula (45) or on different benzene rings. For example, in the case of having three ring structures, one ring structure may exist on each of the three benzene rings of the general formula (45).
[2111] Examples of the above-mentioned ring structures in the compound represented by the above general formula (45) include structures represented by the following general formulas (451) to (460).
[2112] [Tue 165]
[2113]
[2114] (In the above general formulas (451) to (457),
[2115] Each of *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14 is R n and R n+1This represents the two ring-forming carbon atoms bonding together,
[2116] R n The bonding ring-forming carbon atoms may be any of the two ring-forming carbon atoms represented by *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14, and
[2117] X 45 is C(R 4512 )(R 4513 ), NR 4514 , is an oxygen atom or a sulfur atom,
[2118] R 4501 ~R 4506 and R 4512 ~R 4513 One or more of the groups consisting of two or more adjacent groups
[2119] They combine with each other to form a substituted or unsubstituted single ring,
[2120] They combine with each other to form substituted or unsubstituted condensed rings, or
[2121] Without combining with each other,
[2122] R that does not form the above-mentioned single ring and also does not form the above-mentioned condensed ring 4501 ~R 4514 Each independently R in the above general formula (45) 461 ~R 471 It has the same meaning as.)
[2123] [Tuesday 166]
[2124]
[2125] (In the above general formulas (458) to (460),
[2126] Each of *1 and *2, and *3 and *4 is R n and R n+1 This represents the two ring-forming carbon atoms bonding together,
[2127] R nThe bonding ring-forming carbon atom may be either of the two ring-forming carbon atoms represented by *1 and *2, or *3 and *4, and
[2128] X 45 is C(R 4512 )(R 4513 ), NR 4514 , is an oxygen atom or a sulfur atom,
[2129] R 4512 ~R 4513 and R 4515 ~R 4525 One or more of the groups consisting of two or more adjacent groups
[2130] They combine with each other to form a substituted or unsubstituted single ring,
[2131] They combine with each other to form substituted or unsubstituted condensed rings, or
[2132] They do not combine with each other,
[2133] R that does not form the above-mentioned single ring and also does not form the above-mentioned condensed ring 4512 ~R 4513 , R 4515 ~R 4521 and R 4522 ~R 4525 , and R 4514 Each independently R in the above general formula (45) 461 ~R 471 It has the same meaning as.)
[2134] In the above general formula (45), R 462 , R 464 , R 465 , R 470 and R 471 At least one of (preferably R 462 , R 465 and R 470 At least one of, more preferably R 462 It is desirable if the ) does not form a ring structure.
[2135] (i) In the above general formula (45), R nand R n+1 Substituent in the case where the ring structure formed by has a substituent,
[2136] (ii) In the above general formula (45), R that does not form a ring structure 461 ~R 471 , and
[2137] (iii) R in equations (451) to (460) 4501 ~R 4514 , R 4515 ~R 4525 Preferably, each independently
[2138] hydrogen atom,
[2139] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2140] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2141] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2142] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2143] -N(R 906 )(R 907 The one indicated by ),
[2144] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
[2145] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, or
[2146] It is any one of the groups selected from the group consisting of the general formulas (461) to (464) below.
[2147] [Tue 167]
[2148]
[2149] (among the above general formulas (461) to (464),
[2150] R d Each independently
[2151] hydrogen atom,
[2152] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2153] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2154] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2155] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2156] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[2157] -O-(R 904 The one indicated by ),
[2158] -S-(R 905 The one indicated by ),
[2159] -N(R 906 )(R 907 The one indicated by ),
[2160] Halogen atoms,
[2161] Cyanogi,
[2162] Nitro,
[2163] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2164] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[2165] X 46 is C(R 801 )(R 802 ), NR 803 , is an oxygen atom or a sulfur atom,
[2166] R 801 , R 802 and R 803 Each independently
[2167] hydrogen atom,
[2168] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2169] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2170] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2171] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[2172] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or
[2173] It is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[2174] R 801 If this plural exists, the plural R 801 They are identical or different from each other,
[2175] R 802 If there are multiple instances of R 802 are identical or different from each other,
[2176] R 803 If this plural exists, the plural R 803 They are identical or different from each other,
[2177] p1 is 5, and
[2178] p2 is 4, and
[2179] p3 is 3, and
[2180] p4 is 7, and
[2181] In the above general formulas (461) to (464), * each independently indicates the position of connection with the ring structure.
[2182] In a fluorescently emitting compound (compound M1), R 901 ~R 907 It is as defined as tactics.
[2183] In one embodiment, the compound represented by the general formula (45) is represented by any one of the following general formulas (45-1) to (45-6).
[2184] [Tue 168]
[2185]
[2186] [Tue 169]
[2187]
[2188] (In the above general formulas (45-1) to (45-6),
[2189] Rings d~i are each independently a single ring of substitution or a condensed ring of substitution or a condensed ring of substitution or a condensed ring, and
[2190] R 461 ~R 471 Each independently R in the above general formula (45) 461 ~R 471 It has the same meaning as.)
[2191] In one embodiment, the compound represented by the general formula (45) is represented by any one of the following general formulas (45-7) to (45-12).
[2192] [Tue 170]
[2193]
[2194] [Tue 171]
[2195]
[2196] (In the above general formulas (45-7) to (45-12),
[2197] Rings d~f, k, and j are each independently a single ring of substitution or a condensed ring of substitution or a condensed ring of substitution or a condensed ring, and
[2198] R 461 ~R 471 Each independently R in the above general formula (45) 461 ~R 471 It has the same meaning as.)
[2199] In one embodiment, the compound represented by the general formula (45) is represented by any one of the following general formulas (45-13) to (45-21).
[2200] [Tue 172]
[2201]
[2202] [Tue 173]
[2203]
[2204] [Tue 174]
[2205]
[2206] (In the above general formulas (45-13) to (45-21),
[2207] Rings d to k are each independently a substituted or unsubstituted single ring or a substituted or unsubstituted condensed ring, and
[2208] R 461 ~R 471 Each independently R in the above general formula (45) 461 ~R 471 It has the same meaning as.)
[2209] As for the substituents in the case where the above ring g or the above ring h has additional substituents, for example,
[2210] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2211] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
[2212] The device represented by the above general formula (461),
[2213] The device represented by the above general formula (463), or
[2214] The above general formula (464) can be used to represent the device.
[2215] In one embodiment, the compound represented by the general formula (45) is represented by any one of the following general formulas (45-22) to (45-25).
[2216] [Tue 175]
[2217]
[2218] (In the above general formulas (45-22) to (45-25),
[2219] X 46 and X 47 Each is independently C(R 801 )(R 802 ), NR 803 , is an oxygen atom or a sulfur atom,
[2220] R 461 ~R 471 And R 481 ~R 488 Each independently R in the above general formula (45) 461 ~R 471 It has the same meaning as .
[2221] R 801 , R 802 and R 803 Each independently
[2222] hydrogen atom,
[2223] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2224] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2225] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2226] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[2227] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or
[2228] It is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[2229] R 801 If this plural exists, the plural R 801 They are identical or different from each other,
[2230] R 802 If there are multiple instances of R 802 are identical or different from each other,
[2231] R 803 If this plural exists, the plural R 803They are identical or different from each other.
[2232] In one embodiment, the compound represented by the above general formula (45) is represented by the following general formula (45-26).
[2233] [Tue 176]
[2234]
[2235] (In the above general formula (45-26),
[2236] X 46 is C(R 801 )(R 802 ), NR 803 , is an oxygen atom or a sulfur atom,
[2237] R 463 , R 464 , R 467 , R 468 , R 471 , and R 481 ~R 492 Each independently R in the above general formula (45) 461 ~R 471 It has the same meaning as .
[2238] R 801 , R 802 and R 803 Each independently
[2239] hydrogen atom,
[2240] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2241] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2242] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2243] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[2244] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or
[2245] It is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[2246] R 801 If this plural exists, the plural R 801 They are identical or different from each other,
[2247] R 802 If there are multiple instances of R 802 are identical or different from each other,
[2248] R 803 If this plural exists, the plural R 803 They are identical or different from each other.
[2249] As for the compound represented by the above general formula (4), for example, the compounds shown below can be cited as specific examples.
[2250] [Tue 177]
[2251]
[2252] [Tue 178]
[2253]
[2254] [Tue 179]
[2255]
[2256] [Tue 180]
[2257]
[2258] [Tue 181]
[2259]
[2260] [Tue 182]
[2261]
[2262] [Tue 183]
[2263]
[2264] [Tue 184]
[2265]
[2266] [Tue 185]
[2267]
[2268] [Painting 186]
[2269]
[2270] [Tue 187]
[2271]
[2272] [Tue 188]
[2273]
[2274] [Tue 189]
[2275]
[2276] [Tue 190]
[2277]
[2278] (Compound represented by general formula (5))
[2279] A compound represented by general formula (5) is described. The compound represented by general formula (5) is a compound corresponding to the compound represented by general formula (41-3) described above.
[2280] [Tue 191]
[2281]
[2282] (In the above general formula (5),
[2283] R 501 ~R 507 and R 511 ~R 517 One or more of the groups consisting of two or more adjacent groups
[2284] They combine with each other to form a substituted or unsubstituted single ring,
[2285] They combine with each other to form substituted or unsubstituted condensed rings, or
[2286] Without combining with each other,
[2287] R that does not form the above-mentioned single ring and also does not form the above-mentioned condensed ring 501 ~R 507 and R511 ~R 517 Each independently
[2288] hydrogen atom,
[2289] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2290] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2291] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2292] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2293] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[2294] -O-(R 904 The one indicated by ),
[2295] -S-(R 905 The one indicated by ),
[2296] -N(R 906 )(R 907 The one indicated by ),
[2297] Halogen atoms,
[2298] Cyanogi,
[2299] Nitro,
[2300] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2301] It is a complex circulator with 5 to 50 atoms forming a ring, either substituent or unsubstituent.
[2302] R 521 and R 522 Each independently
[2303] hydrogen atom,
[2304] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2305] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2306] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2307] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2308] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[2309] -O-(R 904 The one indicated by ),
[2310] -S-(R 905 The one indicated by ),
[2311] -N(R 906 )(R 907 The one indicated by ),
[2312] Halogen atoms,
[2313] Cyanogi,
[2314] Nitro,
[2315] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2316] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[2317] "R 501 ~R 507 and R 511 ~R 517 "One group consisting of two or more adjacent groups" is, for example, R 501 and R 502 A group consisting of, R 502 and R 503 A group consisting of, R 503 and R 504 A group consisting of, R 505 and R 506 A group consisting of, R 506 and R 507 A group consisting of, R 501 and R 502 and R 503 It is a combination of groups, etc., consisting of
[2318] In terms of the temporal form, R501 ~R 507 and R 511 ~R 517 At least one of -N(R 906 )(R 907 It is a device indicated by ).
[2319] In one embodiment, R 501 ~R 507 and R 511 ~R 517 Each independently
[2320] hydrogen atom,
[2321] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2322] It is a complex circulator with 5 to 50 atoms forming a ring, either substituent or unsubstituent.
[2323] In one embodiment, the compound represented by the above general formula (5) is a compound represented by the following general formula (52).
[2324] [Tue 192]
[2325]
[2326] (In the above general formula (52),
[2327] R 531 ~R 534 and R 541 ~R 544 One or more of the groups consisting of two or more adjacent groups
[2328] They combine with each other to form a substituted or unsubstituted single ring,
[2329] They combine with each other to form substituted or unsubstituted condensed rings, or
[2330] Without combining with each other,
[2331] R that does not form the above-mentioned single ring and also does not form the above-mentioned condensed ring 531 ~R 534 , R 541 ~R 544 , and R 551 and R552 Each independently
[2332] hydrogen atom,
[2333] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2334] It is a complex circulating ring with 5 to 50 substituent or unsubstituent atoms, and
[2335] R 561 ~R 564 Each independently
[2336] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2337] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[2338] In one embodiment, the compound represented by the above general formula (5) is a compound represented by the following general formula (53).
[2339] [Painting 193]
[2340]
[2341] (In the above general formula (53), R 551 , R 552 and R 561 ~R 564 Each independently R in the above general formula (52) 551 , R 552 and R 561 ~R 564 It has the same meaning as.)
[2342] In one embodiment, R in the general formula (52) and general formula (53) 561 ~R 564 Each is independently a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms (preferably a phenyl group).
[2343] In one embodiment, R in the general formula (5) 521 and R 522 , R in the above general formula (52) and general formula (53)551 and R 552 is a hydrogen atom.
[2344] In one embodiment, the substituent in the case of "substituent or non-substituent" in the above general formulas (5), (52) and (53) is
[2345] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2346] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2347] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2348] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2349] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2350] It is a complex circulator with 5 to 50 atoms forming a ring, either substituent or unsubstituent.
[2351] As for the compound represented by the above general formula (5), for example, the compounds shown below can be cited as specific examples.
[2352] [Tue 194]
[2353]
[2354] [Tue 195]
[2355]
[2356] [Tue 196]
[2357]
[2358] [Tue 197]
[2359]
[2360] [Tue 198]
[2361]
[2362] [Tue 199]
[2363]
[2364] [Tue 200]
[2365]
[2366] [Tue 201]
[2367]
[2368] [Tue 202]
[2369]
[2370] [Tue 203]
[2371]
[2372] [Tue 204]
[2373]
[2374] [Tue 205]
[2375]
[2376] [Tue 206]
[2377]
[2378] [Tue 207]
[2379]
[2380] [Tue 208]
[2381]
[2382] [Tue 209]
[2383]
[2384] [Tue 210]
[2385]
[2386] [Tue 211]
[2387]
[2388] [Tue 212]
[2389]
[2390] [Tue 213]
[2391]
[2392] [Tue 214]
[2393]
[2394] [Tue 215]
[2395]
[2396] [Tue 216]
[2397]
[2398] [Tue 217]
[2399]
[2400] [Tue 218]
[2401]
[2402] [Tue 219]
[2403]
[2404] [Tue 220]
[2405]
[2406] [Tue 221]
[2407]
[2408] (Compound represented by general formula (6))
[2409] A compound represented by the general formula (6) is described.
[2410] [Tue 222]
[2411]
[2412] (In the above general formula (6),
[2413] Ring a, ring b, and ring c are each independently
[2414] Substituted or unsubstituted ring-forming aromatic hydrocarbon rings having 6 to 50 carbon atoms, or
[2415] It is a complex ring with 5 to 50 substituent or unsubstituent atoms forming a ring, and
[2416] R 601 and R 602 Each independently combines with the above-mentioned ring a, ring b, or ring c to form a complex ring with or without substitution, or without forming a complex ring with or without substitution,
[2417] R that does not form the above-mentioned or non-substitutive complex ring 601 and R 602 Each independently
[2418] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2419] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2420] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2421] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2422] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2423] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[2424] The a, b, and c rings are rings that are condensed into a condensed two-ring structure in the center of the general formula (6) consisting of a boron atom and two nitrogen atoms (a substituted or unsubstituted ring-forming aromatic hydrocarbon ring with 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming complex ring with 5 to 50 atoms).
[2425] The "aromatic hydrocarbon rings" of the a, b, and c rings have the same structure as the compound in which a hydrogen atom is introduced into the aforementioned "aryl group."
[2426] a The “aromatic hydrocarbon ring” of the ring includes three carbon atoms on the condensed 2-ring structure in the center of the general formula (6) as ring-forming atoms.
[2427] The “aromatic hydrocarbon ring” of the b ring and c ring includes two carbon atoms on the condensed 2-ring structure of the above general formula (6) as ring-forming atoms.
[2428] Specific examples of “substituted or unsubstituted ring-forming aromatic hydrocarbons having 6 to 50 carbon atoms” include compounds in which a hydrogen atom is introduced into the “aryl group” described in Specific Example Group G1.
[2429] The "complex rings" of the a, b, and c rings have the same structure as the compound in which hydrogen atoms are introduced into the aforementioned "complex groups."
[2430] a The “complex ring” of the ring contains three carbon atoms in the condensed two-ring structure of the above general formula (6) as ring-forming atoms. b The “complex ring” of the ring and c contains two carbon atoms in the condensed two-ring structure of the above general formula (6) as ring-forming atoms. Specific examples of “complex rings with 5 to 50 substituent or unsubstituent ring-forming atoms” include compounds in which hydrogen atoms are introduced into the “complex group” described in the group of specific examples G2.
[2431] R 601 and R 602 Each may independently combine with the a ring, b ring, or c ring to form a substitutive or unsubstitutive complex ring. In this case, the complex ring includes a nitrogen atom on the condensed two-ring structure in the center of the general formula (6). In this case, the complex ring may include heteroatoms other than nitrogen atoms. R 601 and R 602 To say that it bonds with the a ring, b ring, or c ring means, specifically, that the atoms constituting the a ring, b ring, or c ring and R 601 and R 602 It means that the atoms constituting it bond. For example, R 601 Combined with this a ring, R 601A nitrogen-containing heterocyclic ring of dicyclic condensation (or tricyclic condensation or higher) may be formed by the condensation of a ring containing and a ring. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to a nitrogen-containing dicyclic condensation or higher heterocyclic group among the specific example group G2.
[2432] R 601 When this b ring combines, R 602 When a combines with a ring, and R 602 The same applies when a c is combined with a ring.
[2433] In one embodiment, the a ring, b ring, and c ring in the above general formula (6) are each independently substituted or unsubstituted ring-forming aromatic hydrocarbon rings having 6 to 50 carbon atoms.
[2434] In one embodiment, the ring a, ring b and ring c in the general formula (6) are each independently substituted or unsubstituted benzene rings or naphthalene rings.
[2435] In one embodiment, R in the general formula (6) 601 and R 602 Each independently
[2436] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2437] It is a complex circulating ring with 5 to 50 substituent or unsubstituent atoms, and
[2438] Preferably, it is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.
[2439] In one embodiment, the compound represented by the above general formula (6) is a compound represented by the following general formula (62).
[2440] [Tue 223]
[2441]
[2442] (In the above general formula (62),
[2443] R 601A is R 611 and R 621 By combining with 1 or more selected from the group consisting of to form a permuted or unpermuted complex, or not forming a permuted or unpermuted complex,
[2444] R 602A is R 613 and R 614 By combining with 1 or more selected from the group consisting of to form a permuted or unpermuted complex, or not forming a permuted or unpermuted complex,
[2445] R that does not form the above-mentioned or non-substitutive complex ring 601A and R 602A Each independently
[2446] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2447] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2448] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2449] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2450] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2451] It is a complex circulating ring with 5 to 50 substituent or unsubstituent atoms, and
[2452] R 611 ~R 621 One or more of the groups consisting of two or more adjacent groups
[2453] They combine with each other to form a substituted or unsubstituted single ring,
[2454] They combine with each other to form substituted or unsubstituted condensed rings, or
[2455] Without combining with each other,
[2456] R that does not form the above-mentioned or non-substitutive complex ring, does not form the above-mentioned single ring, and also does not form the above-mentioned condensation ring 611 ~R 621 Each independently
[2457] hydrogen atom,
[2458] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2459] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2460] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2461] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2462] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[2463] -O-(R 904 The one indicated by ),
[2464] -S-(R 905 The one indicated by ),
[2465] -N(R 906 )(R 907 The one indicated by ),
[2466] Halogen atoms,
[2467] Cyanogi,
[2468] Nitro,
[2469] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2470] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[2471] R of the above general formula (62) 601A and R 602A are each R of the above general formula (6). 601 and R 602 It is a corresponding unit.
[2472] For example, R 601Aand R 611 By combining, a nitrogen-containing heterocyclic ring of dicyclic condensation (or tricyclic condensation or higher) may be formed by the condensation of a ring containing these elements and a benzene ring corresponding to the a ring. Specific examples of the above nitrogen-containing heterocyclic ring include compounds corresponding to a nitrogen-containing heterocyclic condensation or higher heterocyclic group among the specific example group G2. R 601A and R 621 In this case, R 602A and R 613 In the case of this combination, and R 602A and R 614 The case where it is combined is the same as above.
[2473] R 611 ~R 621 One or more of the groups consisting of two or more adjacent groups
[2474] They combine with each other to form a substituted or unsubstituted single ring, or
[2475] They may combine with each other to form substituted or non-substituted condensed rings.
[2476] For example, R 611 and R 612 A structure may be formed in which a benzene ring, indole ring, pyrrole ring, benzofuran ring, or benzothiophene ring is condensed with respect to the six-membered ring to which they are bonded, and the formed condensed ring becomes a naphthalene ring, carbazole ring, indole ring, dibenzofuran ring, or dibenzothiophene ring.
[2477] In one embodiment, R that does not contribute to ring formation 611 ~R 621 Each independently
[2478] hydrogen atom,
[2479] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2480] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2481] It is a complex circulator with 5 to 50 atoms forming a ring, either substituent or unsubstituent.
[2482] In one embodiment, R that does not contribute to ring formation 611 ~R 621 Each independently
[2483] hydrogen atom,
[2484] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2485] It is a complex circulator with 5 to 50 atoms forming a ring, either substituent or unsubstituent.
[2486] In one embodiment, R that does not contribute to ring formation 611 ~R 621 Each independently
[2487] hydrogen atoms, or
[2488] It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[2489] In one embodiment, R that does not contribute to ring formation 611 ~R 621 Each independently
[2490] hydrogen atoms, or
[2491] It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and
[2492] R 611 ~R 621 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[2493] In one embodiment, the compound represented by the general formula (62) is a compound represented by the following general formula (63).
[2494] [Tue 224]
[2495]
[2496] (In the above general formula (63),
[2497] R 631 is R 646Combined with to form a permuted or non-permuted complex, or without forming a permuted or non-permuted complex,
[2498] R 633 is R 647 Combined with to form a permuted or non-permuted complex, or not form a permuted or non-permuted complex,
[2499] R 634 is R 651 Combined with to form a permuted or non-permuted complex, or without forming a permuted or non-permuted complex,
[2500] R 641 is R 642 Combined with to form a permuted or non-permuted complex, or not form a permuted or non-permuted complex,
[2501] R 631 ~R 651 One or more of the groups consisting of two or more adjacent groups
[2502] They combine with each other to form a substituted or unsubstituted single ring,
[2503] They combine with each other to form substituted or unsubstituted condensed rings, or
[2504] Without combining with each other,
[2505] R that does not form the above-mentioned substitution or non-substitution complex ring, does not form the above-mentioned simple ring, and also does not form the above-mentioned condensation ring 631 ~R 651 Each independently
[2506] hydrogen atom,
[2507] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2508] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2509] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2510] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2511] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[2512] -O-(R 904 The one indicated by ),
[2513] -S-(R 905 The one indicated by ),
[2514] -N(R 906 )(R 907 The one indicated by ),
[2515] Halogen atoms,
[2516] Cyanogi,
[2517] Nitro,
[2518] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2519] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[2520] R 631 is R 646 It may be combined with to form a permuted or non-permuted complex ring. For example, R 631 and R 646 In combination, R 646 It is also possible to form a nitrogen-containing heterocyclic ring formed by the condensation of the bonding benzene ring, a ring containing N, and a benzene ring corresponding to the a ring. Specific examples of the above nitrogen-containing heterocyclic ring include compounds corresponding to a nitrogen-containing heterocyclic condensed heterocyclic group of specific examples G2. R 633 and R 647 In this case, R 634 and R 651 In the case of this combination, and R 641 and R 642 The case where it is combined is the same as above.
[2521] In one embodiment, R that does not contribute to ring formation631 ~R 651 Each independently
[2522] hydrogen atom,
[2523] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2524] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2525] It is a complex circulator with 5 to 50 atoms forming a ring, either substituent or unsubstituent.
[2526] In one embodiment, R that does not contribute to ring formation 631 ~R 651 Each independently
[2527] hydrogen atom,
[2528] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2529] It is a complex circulator with 5 to 50 atoms forming a ring, either substituent or unsubstituent.
[2530] In one embodiment, R that does not contribute to ring formation 631 ~R 651 Each independently
[2531] hydrogen atoms, or
[2532] It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[2533] In one embodiment, R that does not contribute to ring formation 631 ~R 651 Each independently
[2534] hydrogen atoms, or
[2535] It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and
[2536] R 631 ~R 651 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[2537] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63A).
[2538] [Tue 225]
[2539]
[2540] (In the above general formula (63A),
[2541] R 661 silver
[2542] hydrogen atom,
[2543] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2544] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2545] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2546] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms, or
[2547] It is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[2548] R 662 ~R 665 Each independently
[2549] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2550] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2551] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2552] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms, or
[2553] It is a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms.
[2554] In one embodiment, R 661 ~R 665 Each independently
[2555] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or
[2556] It is a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms.
[2557] In one embodiment, R 661 ~R 665 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[2558] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63B).
[2559] [Tue 226]
[2560]
[2561] (In the above general formula (63B),
[2562] R 671 and R 672 Each independently
[2563] hydrogen atom,
[2564] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2565] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2566] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2567] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2568] -N(R 906 )(R 907 The unit indicated by ), or
[2569] It is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[2570] R 673 ~R 675 Each independently
[2571] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2572] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2573] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2574] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2575] -N(R 906 )(R 907 The unit indicated by ), or
[2576] It is a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms.
[2577] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63B').
[2578] [Tue 227]
[2579]
[2580] (In the above general formula (63B'), R 672 ~R 675 R in the above general formula (63B) is independently 672 ~R 675 It has the same meaning as.)
[2581] In one embodiment, R 671 ~R 675 At least one of them,
[2582] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2583] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2584] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2585] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2586] -N(R 906 )(R 907 The unit indicated by ), or
[2587] It is a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms.
[2588] In one embodiment,
[2589] R 672 Is
[2590] hydrogen atom,
[2591] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2592] -N(R 906 )(R 907 The unit indicated by ), or
[2593] It is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and
[2594] R 671 and R 673 ~R 675 Each independently
[2595] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2596] -N(R 906 )(R 907 The unit indicated by ), or
[2597] It is a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms.
[2598] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63C).
[2599] [Tue 228]
[2600]
[2601] (In the above general formula (63C),
[2602] R 681 and R 682 Each independently
[2603] hydrogen atom,
[2604] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2605] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2606] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2607] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms, or
[2608] It is a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms.
[2609] R 683 ~R 686 Each independently
[2610] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2611] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2612] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2613] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms, or
[2614] It is a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms.
[2615] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63C').
[2616] [Tue 229]
[2617]
[2618] (In the above general formula (63C'), R 683 ~R 686 Each is independently R in the above general formula (63C). 683 ~R 686 It has the same meaning as.)
[2619] In one embodiment, R 681 ~R 686 Each independently
[2620] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or
[2621] It is a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms.
[2622] In one embodiment, R 681 ~R 686 Each is independently a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms.
[2623] The compound represented by the above general formula (6) is, first, a ring a, a ring b, and a ring c formed by a linker (NR 601 The group including and NR 602 An intermediate can be prepared by combining with a group (containing a boron atom) (first reaction), and a final product can be prepared by combining the a ring, b ring, and c ring with a linker (a group containing a boron atom) (second reaction). In the first reaction, an amination reaction such as the Buchwald-Hartwig reaction can be applied. In the second reaction, the Tandem Hetero-Friedel-Crafts reaction can be applied.
[2624] Specific examples of compounds represented by the above general formula (6) are described below, but these are merely examples and the compounds represented by the above general formula (6) are not limited to the following specific examples.
[2625] [Tue 230]
[2626]
[2627] [Tue 231]
[2628]
[2629] [Tue 232]
[2630]
[2631] [Tue 233]
[2632]
[2633] [Tue 234]
[2634]
[2635] [Tue 235]
[2636]
[2637] [Tue 236]
[2638]
[2639] [Tue 237]
[2640]
[2641] [Tue 238]
[2642]
[2643] [Tue 239]
[2644]
[2645] [Tue 240]
[2646]
[2647] [Tue 241]
[2648]
[2649] [Tue 242]
[2650]
[2651] [Tue 243]
[2652]
[2653] [Tue 244]
[2654]
[2655] [Tue 245]
[2656]
[2657] [Tue 246]
[2658]
[2659] (Compound represented by general formula (7))
[2660] A compound represented by the general formula (7) is described.
[2661] [Tue 247]
[2662]
[2663] [Tue 248]
[2664]
[2665] (In the above general formula (7),
[2666] The r ring is a ring represented by the above general formula (72) or general formula (73) that condenses at any position of an adjacent ring, and
[2667] The q ring and the s ring are each rings represented by the general formula (74) that condense independently at any position of adjacent rings, and
[2668] The p-ring and t-ring are structures represented by the above general formula (75) or general formula (76) that condense independently at any position of adjacent rings, and
[2669] X7 is an oxygen atom, a sulfur atom, or NR 702 am.
[2670] R 701 If multiple exist, adjacent multiple R 701 silver
[2671] They combine with each other to form a substituted or unsubstituted single ring,
[2672] They combine with each other to form substituted or unsubstituted condensed rings, or
[2673] Without combining with each other,
[2674] R that does not form the above-mentioned single ring and also does not form the above-mentioned condensed ring 701 and R 702 Each independently
[2675] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2676] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2677] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2678] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2679] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[2680] -O-(R 904 The one indicated by ),
[2681] -S-(R 905 The one indicated by ),
[2682] -N(R 906 )(R 907 The one indicated by ),
[2683] Halogen atoms,
[2684] Cyanogi,
[2685] Nitro,
[2686] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2687] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[2688] Ar 701 and Ar 702 Each independently
[2689] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2690] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2691] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2692] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2693] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2694] It is a complex circulating ring with 5 to 50 substituent or unsubstituent atoms, and
[2695] L 701 silver
[2696] Substituted or unsubstituted alkylene groups having 1 to 50 carbon atoms,
[2697] Substituted or unsubstituted alkenylene groups having 2 to 50 carbon atoms,
[2698] Substituted or unsubstituted alkynylene groups having 2 to 50 carbon atoms,
[2699] Substituted or unsubstituted ring-forming cycloalkylene groups having 3 to 50 carbon atoms,
[2700] Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, or
[2701] It is a divalent complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[2702] m1 is 0, 1, or 2, and
[2703] m2 is 0, 1, 2, 3, or 4, and
[2704] m3 are each independently 0, 1, 2, or 3, and
[2705] m4 are each independently 0, 1, 2, 3, 4, or 5, and
[2706] R 701 If this plural exists, the plural R 701 They are identical or different from each other,
[2707] If there are multiple X7s, the multiple X7s are identical or different from each other, and
[2708] R 702 If there are multiple instances of R 702 are identical or different from each other,
[2709] Ar 701 If this plural exists, the plural Ar 701 They are identical or different from each other,
[2710] Ar 702 If there are multiple Ar 702 are identical or different from each other,
[2711] L 701If this plural exists, the plural L 701 They are identical or different from each other.
[2712] In the above general formula (7), each ring of the p ring, q ring, r ring, s ring, and t ring condenses by sharing two carbon atoms with an adjacent ring. The position and direction of condensation are not limited, and condensation can occur at any position and direction.
[2713] In one embodiment, in the above general formula (72) or general formula (73) as an r ring, m1=0 or m2=0.
[2714] In one embodiment, the compound represented by the above general formula (7) is represented by any one of the following general formulas (71-1) to (71-6).
[2715] [Tue 249]
[2716]
[2717] [Tue 250]
[2718]
[2719] [Tue 251]
[2720]
[2721] [Tue 252]
[2722]
[2723] [Tue 253]
[2724]
[2725] [Tue 254]
[2726]
[2727] (In the above general formulas (71-1) to (71-6), R 701 , X7, Ar 701 , Ar 702 , L 701 , m1 and m3 are each R in the above general formula (7). 701, X7, Ar 701 , Ar 702 , L 701 , has the same meaning as m1 and m3.)
[2728] In one embodiment, the compound represented by the above general formula (7) is represented by any one of the following general formulas (71-11) to (71-13).
[2729] [Tue 255]
[2730]
[2731] [Tue 256]
[2732]
[2733] [Tue 257]
[2734]
[2735] (In the above general formulas (71-11) to (71-13), R 701 , X7, Ar 701 , Ar 702 , L 701 , m1, m3 and m4 are each R in the above general formula (7). 701 , X7, Ar 701 , Ar 702 , L 701 , has the same meaning as m1, m3, and m4.)
[2736] In one embodiment, the compound represented by the above general formula (7) is represented by any one of the following general formulas (71-21) to (71-25).
[2737] [Tue 258]
[2738]
[2739] [Tue 259]
[2740]
[2741] [Tue 260]
[2742]
[2743] [Tue 261]
[2744]
[2745] [Tue 262]
[2746]
[2747] (In the above general formulas (71-21) to (71-25), R 701 , X7, Ar 701 , Ar 702 , L 701 , m1 and m4 are each R in the above general formula (7). 701 , X7, Ar 701 , Ar 702 , L 701 , has the same meaning as m1 and m4.)
[2748] In one embodiment, the compound represented by the above general formula (7) is represented by any one of the following general formulas (71-31) to general formula (71-33).
[2749] [Tue 263]
[2750]
[2751] [Tue 264]
[2752]
[2753] [Tue 265]
[2754]
[2755] (In the above general formulas (71-31) to (71-33), R 701 , X7, Ar 701 , Ar 702 , L 701 , m2~m4 are each R in the above general formula (7). 701 , X7, Ar 701 , Ar 702 , L 701 , it has the same meaning as m2~m4.)
[2756] In one embodiment, Ar 701 and Ar 702Each is an independently substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms.
[2757] In one embodiment, Ar 701 and Ar 702 One of them is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and Ar 701 and Ar 702 The other side is a complex circulator with 5 to 50 ring-forming atoms, either substituent or non-substituent.
[2758] As for the compound represented by the above general formula (7), for example, the compound shown below can be cited as a specific example.
[2759] [Tue 266]
[2760]
[2761] [Tue 267]
[2762]
[2763] [Tue 268]
[2764]
[2765] [Tue 269]
[2766]
[2767] [Tue 270]
[2768]
[2769] [Tue 271]
[2770]
[2771] [Tue 272]
[2772]
[2773] [Tue 273]
[2774]
[2775] [Tue 274]
[2776]
[2777] [Tue 275]
[2778]
[2779] [Tue 276]
[2780]
[2781] (Compound represented by general formula (8))
[2782] A compound represented by the general formula (8) is described.
[2783] [Tue 277]
[2784]
[2785] (In the above general formula (8),
[2786] R 801 and R 802 , R 802 and R 803 , and R 803 and R 804 At least one of the sets combines with each other to form a divalent group represented by the following general formula (82), and
[2787] R 805 and R 806 , R 806 and R 807 , and R 807 and R 808 At least one of the sets combines with each other to form a divalent group represented by the following general formula (83).)
[2788] [Tue 278]
[2789]
[2790] (R that does not form a divalent group represented by the above general formula (82) 801 ~R 804 , and R 811 ~R 814 At least one of them is a univalent element represented by the following general formula (84), and
[2791] R that does not form a divalent group represented by the above general formula (83). 805 ~R 808 , and R 821~R 824 At least one of them is a univalent element represented by the following general formula (84), and
[2792] X8 is an oxygen atom, a sulfur atom, or NR 809 is,
[2793] R that does not form a divalent group represented by the above general formulas (82) and (83), and also is not a monovalent group represented by the above general formula (84). 801 ~R 808 , R that is not a monovalent group represented by the above general formula (84) 811 ~R 814 and R 821 ~R 824 , and R 809 Each independently
[2794] hydrogen atom,
[2795] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2796] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2797] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2798] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2799] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[2800] -O-(R 904 The one indicated by ),
[2801] -S-(R 905 The one indicated by ),
[2802] -N(R 906 )(R 907 The one indicated by ),
[2803] Halogen atoms,
[2804] Cyanogi,
[2805] Nitro,
[2806] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2807] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[2808] [Tue 279]
[2809]
[2810] (In the above general formula (84),
[2811] Ar 801 and Ar 802 Each independently
[2812] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2813] It is a complex circulating ring with 5 to 50 substituent or unsubstituent atoms, and
[2814] L 801 ~L 803 Each independently
[2815] single bond,
[2816] Substituted or unsubstituted ring-forming arylene groups having 6 to 30 carbon atoms,
[2817] A divalent complex circulator with 5 to 30 atoms forming a ring, either substituted or unsubstituted, or
[2818] It is a divalent linker formed by combining 2 to 4 groups selected from the group consisting of a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted ring-forming divalent complex cyclic group having 5 to 30 atoms, and
[2819] In the above general formula (84), * indicates the connection position of the ring structure represented by the above general formula (8), the general formula (82), or the general formula (83).
[2820] In the above general formula (8), the location where the divalent group represented by the general formula (82) and the divalent group represented by the general formula (83) are formed is not particularly limited, and R 801~R 808 The above device can be formed in a possible location.
[2821] In one embodiment, the compound represented by the above general formula (8) is represented by any one of the following general formulas (81-1) to (81-6).
[2822] [Tue 280]
[2823]
[2824] [Tue 281]
[2825]
[2826] [Tue 282]
[2827]
[2828] (In the above general formulas (81-1) to (81-6),
[2829] X8 has the same meaning as X8 in the above general formula (8), and
[2830] R 801 ~R 824 At least two of them are univalent elements represented by the above general formula (84), and
[2831] R that is not a monovalent group represented by the above general formula (84). 801 ~R 824 Each independently
[2832] hydrogen atom,
[2833] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2834] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2835] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2836] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2837] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[2838] -O-(R 904 The one indicated by ),
[2839] -S-(R 905 The one indicated by ),
[2840] -N(R 906 )(R 907 The one indicated by ),
[2841] Halogen atoms,
[2842] Cyanogi,
[2843] Nitro,
[2844] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2845] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[2846] In one embodiment, the compound represented by the above general formula (8) is represented by any one of the following general formulas (81-7) to (81-18).
[2847] [Tue 283]
[2848]
[2849] [Tue 284]
[2850]
[2851] [Tue 285]
[2852]
[2853] [Tue 286]
[2854]
[2855] [Tue 287]
[2856]
[2857] [Tue 288]
[2858]
[2859] (In the above general formulas (81-7) to (81-18),
[2860] X8 has the same meaning as X8 in the above general formula (8), and
[2861] * is a single bond that combines with a univalent group represented by the above general formula (84), and
[2862] R 801 ~R 824 R is not a monovalent group represented by the general formula (84) in the general formulas (81-1) to (81-6), each independently 801 ~R 824 It has the same meaning as.)
[2863] R that does not form a divalent group represented by the above general formulas (82) and (83), and also is not a monovalent group represented by the above general formula (84). 801 ~R 808 , and, R that is not a monovalent group represented by the above general formula (84). 811 ~R 814 and R 821 ~R 824 are, preferably, each independently
[2864] hydrogen atom,
[2865] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2866] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2867] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2868] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2869] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2870] It is a complex circulator with 5 to 50 atoms forming a ring, either substituent or unsubstituent.
[2871] The univalent group represented by the above general formula (84) is preferably represented by the following general formula (85) or general formula (86).
[2872] [Tue 289]
[2873]
[2874] (In the above general formula (85),
[2875] R 831 ~R 840 Each independently
[2876] hydrogen atom,
[2877] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2878] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2879] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2880] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2881] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[2882] -O-(R 904 The one indicated by ),
[2883] -S-(R 905 The one indicated by ),
[2884] -N(R 906 )(R 907 The one indicated by ),
[2885] Halogen atoms,
[2886] Cyanogi,
[2887] Nitro,
[2888] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2889] It is a complex circulating ring with 5 to 50 substituent or unsubstituent atoms, and
[2890] The * in the above general formula (85) has the same meaning as the * in the above general formula (84).
[2891] [Tue 290]
[2892]
[2893] (In the above general formula (86),
[2894] Ar 801 , L 801 and L 803 Ar in the above general formula (84) 801 , L 801 and L 803 It has the same meaning as,
[2895] HAr 801 is a structure represented by the following general formula (87).
[2896] [Tue 291]
[2897]
[2898] (In the above general formula (87),
[2899] X 81 It is an oxygen atom or a sulfur atom, and
[2900] R 841 ~R 848 One of them is L 803 It is a single bond that binds to,
[2901] R that is not a single bond 841 ~R 848 Each independently
[2902] hydrogen atom,
[2903] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2904] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2905] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2906] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2907] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[2908] -O-(R 904 The one indicated by ),
[2909] -S-(R 905 The one indicated by ),
[2910] -N(R 906 )(R 907 The one indicated by ),
[2911] Halogen atoms,
[2912] Cyanogi,
[2913] Nitro,
[2914] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2915] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[2916] As for the compound represented by the above general formula (8), in addition to the compound described in International Publication No. 2014 / 104144, for example, the compound shown below may be cited as a specific example.
[2917] [Tue 292]
[2918]
[2919] [Tue 293]
[2920]
[2921] [Tue 294]
[2922]
[2923] [Tue 295]
[2924]
[2925] [Tue 296]
[2926]
[2927] [Tue 297]
[2928]
[2929] [Tue 298]
[2930]
[2931] [Tue 299]
[2932]
[2933] [Tue 300]
[2934]
[2935] [Tue 301]
[2936]
[2937] (Compound represented by general formula (9))
[2938] A compound represented by the general formula (9) is described.
[2939] [Tue 302]
[2940]
[2941] (In the above general formula (9),
[2942] A 91 ring and A 92 Each ring independently
[2943] Substituted or unsubstituted ring-forming aromatic hydrocarbon rings having 6 to 50 carbon atoms, or,
[2944] It is a complex ring with 5 to 50 substituent or unsubstituent atoms forming a ring, and
[2945] A 91 ring and A 92 One or more rings selected from a group of rings are
[2946] Combines with * of the structure represented by the following general formula (92).
[2947] [Tue 303]
[2948]
[2949] (In the above general formula (92),
[2950] A 93 The ring
[2951] Substituted or unsubstituted ring-forming aromatic hydrocarbon rings having 6 to 50 carbon atoms, or,
[2952] It is a complex ring with 5 to 50 substituent or unsubstituent atoms forming a ring, and
[2953] X9 is NR 93 , C(R 94 )(R 95 ), Si(R 96 )(R 97 ), Ge(R 98 )(R 99 ), oxygen atoms, sulfur atoms, or selenium atoms,
[2954] R 91 and R 92 Is
[2955] They combine with each other to form a substituted or unsubstituted single ring,
[2956] They combine with each other to form substituted or unsubstituted condensed rings, or
[2957] They do not combine with each other,
[2958] R that does not form the above-mentioned single ring and also does not form the above-mentioned condensed ring 91 and R 92 , and R 93 ~R 99 Each independently
[2959] hydrogen atom,
[2960] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2961] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[2962] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[2963] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[2964] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[2965] -O-(R 904 The one indicated by ),
[2966] -S-(R 905The one indicated by ),
[2967] -N(R 906 )(R 907 The one indicated by ),
[2968] Halogen atoms,
[2969] Cyanogi,
[2970] Nitro,
[2971] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2972] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.
[2973] A 91 ring and A 92 One or more rings selected from a group of rings are combined with * of the structure represented by the general formula (92) above. That is, in one embodiment, A 91 The ring-forming carbon atom of the above aromatic hydrocarbon ring of the ring, or the ring-forming atom of the above heterocyclic ring, is bonded to * of the structure represented by the above general formula (92). In addition, in one embodiment, A 92 The ring-forming carbon atom of the above aromatic hydrocarbon ring, or the ring-forming atom of the above heterocyclic ring, is bonded to the * of the structure represented by the above general formula (92).
[2974] In one embodiment, A 91 ring and A 92 A ring is combined with one or both rings, represented by the following general formula (93).
[2975] [Tue 304]
[2976]
[2977] (In the above general formula (93),
[2978] Ar 91 and Ar 92 Each independently
[2979] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[2980] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[2981] L 91 ~L 93 Each independently
[2982] single bond,
[2983] Substituted or unsubstituted ring-forming arylene groups having 6 to 30 carbon atoms,
[2984] A divalent complex circulator with 5 to 30 atoms forming a ring, either substituted or unsubstituted, or
[2985] It is a divalent linker formed by the bonding of 2 to 4 groups selected from the group consisting of a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted ring-forming divalent complex cyclic group having 5 to 30 atoms, and
[2986] In the above general formula (93), * is A 91 ring and A 92 Indicates the connection position with any one of the rings.)
[2987] In one embodiment, A 91 In addition to the ring, A 92 The ring-forming carbon atom of the above-mentioned aromatic hydrocarbon ring or the ring-forming atom of the above-mentioned heterocyclic ring is bonded to the * of the structure represented by the above-mentioned general formula (92). In this case, the structures represented by the above-mentioned general formula (92) may be identical or different from each other.
[2988] In one embodiment, R 91 and R 92 Each is independently a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.
[2989] In one embodiment, R 91 and R 92 They combine with each other to form a fluorene structure.
[2990] In one embodiment, ring A 91 and ring A 92 Each is independently a substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 50 carbon atoms, for example, a substituted or unsubstituted benzene ring.
[2991] In one embodiment, ring A 93 It is a substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 50 carbon atoms, for example, a substituted or unsubstituted benzene ring.
[2992] In one embodiment, X9 is an oxygen atom or a sulfur atom.
[2993] As for the compound represented by the above general formula (9), for example, the compound shown below can be cited as a specific example.
[2994] [Tue 305]
[2995]
[2996] [Tue 306]
[2997]
[2998] [Tue 307]
[2999]
[3000] [Tue 308]
[3001]
[3002] [Tue 309]
[3003]
[3004] [Tue 310]
[3005]
[3006] [Tue 311]
[3007]
[3008] [Tue 312]
[3009]
[3010] (Compound represented by general formula (10))
[3011] A compound represented by the general formula (10) is described.
[3012] [Tue 313]
[3013]
[3014] [Tue 314]
[3015]
[3016] (In the above general formula (10),
[3017] Ax1 is a ring represented by the above general formula (10a) that condenses at any position of an adjacent ring, and
[3018] Ax2 is a ring represented by the above general formula (10b) that condenses at any position of an adjacent ring, and
[3019] Two *s in the above general formula (10b) are combined with any position of the Ax3 ring, and
[3020] X A and X B Each is independently C(R 1003 )(R 1004 ), Si(R 1005 )(R 1006 ), is an oxygen atom or a sulfur atom,
[3021] Ax3 ring
[3022] Substituted or unsubstituted ring-forming aromatic hydrocarbon rings having 6 to 50 carbon atoms, or
[3023] It is a complex ring with 5 to 50 substituent or unsubstituent atoms forming a ring, and
[3024] Ar 1001 silver
[3025] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[3026] It is a complex circulating ring with 5 to 50 substituent or unsubstituent atoms, and
[3027] R 1001~R 1006 Each independently
[3028] hydrogen atom,
[3029] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[3030] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
[3031] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
[3032] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,
[3033] -Si(R 901 )(R 902 )(R 903 The one indicated by ),
[3034] -O-(R 904 The one indicated by ),
[3035] -S-(R 905 The one indicated by ),
[3036] -N(R 906 )(R 907 The one indicated by ),
[3037] Halogen atoms,
[3038] Cyanogi,
[3039] Nitro,
[3040] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or
[3041] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and
[3042] mx1 is 3, mx2 is 2, and
[3043] Multiple R 1001 They are identical or different from each other,
[3044] Multiple R 1002 are identical or different from each other,
[3045] ax is 0, 1, or 2, and
[3046] If ax is 0 or 1, the structure inside the parentheses, denoted as "3-ax", is either identical or different, and
[3047] When ax is 2, multiple Ar 1001 They are identical or different from each other.
[3048] In one embodiment, Ar 1001 It is a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms.
[3049] In one embodiment, the Ax3 ring is a substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 50 carbon atoms, for example, a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted anthracene ring.
[3050] In one embodiment, R 1003 and R 1004 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[3051] In one embodiment, ax is 1.
[3052] As for the compound represented by the above general formula (10), for example, the compound shown below can be cited as a specific example.
[3053] [Tue 315]
[3054]
[3055] [Tue 316]
[3056]
[3057] In one embodiment, the light-emitting layer,
[3058] A compound...
Claims
Claim 1 A compound represented by the following general formula (120). (In the above general formula (120), L1 is represented by any one of the following general formulas (11) to (13), and L2 is represented by any one of the following general formulas (11A) to (13A), R 102 ~R 119 are each independently a hydrogen atom, a substituted or unsubstituted C1-50 alkyl group, a substituted or unsubstituted C3-50 cycloalkyl group, a group represented by -Si(Rx)(Ry)(Rz), a substituted or unsubstituted ring-forming C6-50 aryl group, or a substituted or unsubstituted ring-forming heterocyclic group with 5-50 atoms, and in -Si(Rx)(Ry)(Rz), Rx, Ry, and Rz are each independently a substituted or unsubstituted C1-50 alkyl group, or a substituted or unsubstituted ring-forming C6-50 aryl group, and R 102 ~R 119 In the case of "substituted or unsubstituted," "substitution" refers to being independently substituted by an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted terphenyl group, an unsubstituted naphthyl group, an unsubstituted anthryl group, an unsubstituted phenanthryl group, an unsubstituted chrysenyl group, an unsubstituted triphenylenyl group, an unsubstituted fluorenyl group, an unsubstituted 9,9'-spirobifluorenyl group, an unsubstituted 9,9-dimethylfluorenyl group, or an unsubstituted 9,9-diphenylfluorenyl group. (In the above general formulas (11) to (13) and (11A) to (13A), R 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A , and R 31A ~R 37A 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 carbon atoms, a group represented by -Si(Rx)(Ry)(Rz), a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 carbon atoms, wherein Rx, Ry, and Rz in -Si(Rx)(Ry)(Rz) are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, provided that R 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37, R 11A ~R 15A , R 21A ~R 27A and R 31A ~R 37A The “substituted or unsubstituted cyclic aryl groups having 6 to 50 carbon atoms” represented by is each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group, and R 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37, R 11A ~R 15A , R 21A ~R 27A and R 31A ~R 37A In the case of "substituted or unsubstituted," "substitution" refers to being independently substituted by an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted terphenyl group, an unsubstituted naphthyl group, an unsubstituted anthryl group, an unsubstituted phenanthryl group, an unsubstituted chrysenyl group, an unsubstituted triphenylenyl group, an unsubstituted fluorenyl group, an unsubstituted 9,9'-spirobifluorenyl group, an unsubstituted 9,9-dimethylfluorenyl group, or an unsubstituted 9,9-diphenylfluorenyl group, and R 11 ~R 15 Among them, one or more of the groups consisting of two or more adjacent groups do not combine with each other to form a single ring of substitution or non-substitution, and also do not form a condensed ring of substitution or non-substitution, R 11A ~R 15A Among them, one or more of the groups consisting of two or more adjacent groups do not combine with each other to form a single ring of substitution or non-substitution, and also do not form a condensed ring of substitution or non-substitution, R 21 ~R 27 Among them, one or more of the groups consisting of two or more adjacent groups do not combine with each other to form a single ring of substitution or non-substitution, and also do not form a condensed ring of substitution or non-substitution, R 21A ~R 27A Among them, one or more of the groups consisting of two or more adjacent groups do not combine with each other to form a single ring of substitution or non-substitution, and also do not form a condensed ring of substitution or non-substitution, R 31 ~R 37 Among them, one or more of the groups consisting of two or more adjacent groups do not combine with each other to form a single ring of substitution or non-substitution, and also do not form a condensed ring of substitution or non-substitution, R 31A ~R 37A Among the above, at least one set of two or more adjacent sets does not combine with each other to form a single ring of substitution or non-substitution, and also does not form a condensed ring of substitution or non-substitution, and among the above general formulas (11) to (13) as L1, * indicates the bonding position with *a in the above general formula (120), and R 11 ~R 15 , R 21 ~R 27 and R 31 ~R 37 One of them is a single bond that bonds to L2, and among the above general formulas (11A) to (13A) as L2, * indicates the bonding position with *b in the above general formula (120), and R 11A ~R 15A , R 21A ~R 27A and R 31A ~R 37A One of them is a single bond that binds to L1, provided that R in L1 12 or R 14 When is a single bond that combines with L2, L2's R 11A , R 13A , R 15A , R 21A ~R 27A and R 31A ~R 37A Any one of them is a single bond that combines with L1, and R in L1 11 or R 15 When is a single bond that combines with L2, L2's R 12A , R 13A , R 14A , R 21A ~R 27A and R 31A ~R 37A Any one of them is a single bond that combines with L1, and R in L1 13 When this is a single bond combining with L2, L2's R 11A , R 12A , R 14A , R 15A , R 21A ~R 27A and R 31A ~R 37A Any one of them is a single bond that combines with L1, and R in L1 21 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 22A ~R 27A and R 31A ~R 37A Any one of them is a single bond that combines with L1, and R in L1 22 When is a single bond that combines with L2, L2's R 11A ~R 15A , R 21A , R 23A ~R 27A and R 31A ~R 37A Any one of them is a single bond that combines with L1, and R in L1 23 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 21A ~R 22A , R 24A ~R 27A and R 31A ~R 37A Any one of them is a single bond that combines with L1, and R in L1 24 When is a single bond that combines with L2, L2's R 11A ~R 15A , R 21A ~R 23A , R 25A ~R 27A and R 31A ~R 37A Any one of them is a single bond that combines with L1, and R in L1 25 When is a single bond that combines with L2, L2's R 11A ~R 15A , R 21A ~R 24A , R 26A ~R 27A and R 31A ~R 37A Any one of them is a single bond that combines with L1, and R in L1 26 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 21A ~R 25A , R 27A and R 31A ~R 37A Any one of them is a single bond that combines with L1, and R in L1 27 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 21A ~R 26A and R 31A ~R 37A Any one of them is a single bond that combines with L1, and R in L1 31 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 21A ~R 27A and R 32A ~R 37A Any one of them is a single bond that combines with L1, and R in L1 32 When is a single bond that combines with L2, L2's R 11A ~R 15A , R 21A ~R 27A , R 31A and R 33A ~R 37A Any one of them is a single bond that combines with L1, and R in L1 33 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 21A ~R 27A , R 31A ~R 32A and R 34A ~R 37A Any one of them is a single bond that combines with L1, and R in L1 34 When is a single bond that combines with L2, L2's R 11A ~R 15A , R 21A ~R 27A , R 31A ~R 33A and R 35A ~R 37A Any one of them is a single bond that combines with L1, and R in L1 35 When is a single bond that combines with L2, L2's R 11A ~R 15A , R 21A ~R 27A , R 31A ~R 34A and R 36A ~R 37A Any one of them is a single bond that combines with L1, and R in L1 36 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 21A ~R 27A , R 31A ~R 35A and R 37A Any one of them is a single bond that combines with L1, and R in L1 37 When this is a single bond combining with L2, L2's R 11A ~R 15A , R 21A ~R 27A and R 31A ~R 36A One of them is a single bond that combines with L1.) Claim 2 In claim 1, -L1-L2- is a compound represented by any one of the following general formulas (13-1) to (13-50), (13-52) to (13-57) and (13-59) to (13-69). (In the above general formulas (13-1) to (13-50), (13-52) to (13-57) and (13-59) to (13-69), R 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A and R 31A ~R 37A R in the above general formulas (11) to (13) and (11A) to (13A) are each independently 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A and R 31A ~R 37A It has the same meaning as, and in the above general formulas (13-1) to (13-50), (13-52) to (13-57) and (13-59) to (13-69), *1 indicates the position of combination with *a in the above general formula (120), and *2 indicates the position of combination with *b in the above general formula (120). Claim 3 In claim 1, the compound represented by the above general formula (120) is a compound represented by any one of the following general formulas (121) to (131). (In the above general formulas (121) to (131), R 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A and R 31A ~R 37A R in the above general formulas (11) to (13) and (11A) to (13A) are each independently 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A and R 31A ~R 37A It has the same meaning as, and R 102 ~R 119 R in the above general formula (120) is independently 102 ~R 119 It has the same meaning as.) Claim 4 In any one of paragraphs 1 to 3, R 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A , R 31A ~R 37A and R 102 ~R 119 A compound in which each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 30 carbon atoms, a group represented by -Si(Rx)(Ry)(Rz), a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 30 carbon atoms, and in -Si(Rx)(Ry)(Rz), Rx, Ry, and Rz are each independently an unsubstituted alkyl group having 1 to 30 carbon atoms or an unsubstituted ring-forming aryl group having 6 to 30 carbon atoms. Claim 5 In any one of paragraphs 1 to 3, R 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A , and R 31A ~R 37A Each independently a hydrogen atom, a substituted or unsubstituted C1–18 alkyl group, a substituted or unsubstituted phenyl 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 pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted 1-carbazolyl group, a substituted or unsubstituted 2-carbazolyl group, a substituted or unsubstituted 3-carbazolyl group, substituted or unsubstituted 4-carbazolyl group, substituted or unsubstituted 9-carbazolyl group, substituted or unsubstituted benzocarbazolyl group, substituted or unsubstituted azacarbazolyl group, substituted or unsubstituted diazacarbazolyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted naphthobenzofuranyl group, substituted or unsubstituted azadibenzofuranyl group, substituted or unsubstituted diazadibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted naphthobenzothiophenyl group, substituted or unsubstituted azadibenzothiophenyl group, or substituted or unsubstituted diazadibenzothiophenyl group and R 102 ~R 119 Each independently a hydrogen atom, a substituted or unsubstituted C1–18 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted Quinolyl group, substituted or unsubstituted isoquinolyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted phenanthrolinyl group, substituted or unsubstituted 1-carbazolyl group, substituted or unsubstituted 2-carbazolyl group, substituted or unsubstituted 3-carbazolyl group, substituted or unsubstituted 4-carbazolyl group, substituted or unsubstituted 9-carbazolyl group, substituted or unsubstituted benzocarbazolyl group, substituted or unsubstituted azacarbazolyl group, substituted or unsubstituted dizacarbazolyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted naphthobenzofuranyl group, substituted or unsubstituted azadibenzofuranyl group, substituted or A compound having an unsubstituted diazadibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted naphthobenzothiophenyl group, a substituted or unsubstituted azadibenzothiophenyl group, or a substituted or unsubstituted diazadibenzothiophenyl group. Claim 6 In any one of paragraphs 1 to 3, R 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A , and R 31A ~R 37A Each is independently a hydrogen atom, a substituted or unsubstituted C1–C6 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group, and R 102 ~R 119 A compound in which each is independently a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group. Claim 7 In any one of paragraphs 1 to 3, R 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A and R 31A ~R 37A is a compound consisting of hydrogen atoms. Claim 8 In any one of paragraphs 1 to 3, R 102 ~R 119 is a compound consisting of hydrogen atoms. Claim 9 In any one of paragraphs 1 to 3, R 11 ~R 15 , R 21 ~R 27 , R 31 ~R 37 , R 11A ~R 15A , R 21A ~R 27A , R 31A ~R 37A and R 102 ~R 119 A compound in which, in the case of “substituted or unsubstituted,” “substituted” means, respectively, a compound that is independently substituted by an unsubstituted C1-18 alkyl group, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, an unsubstituted fluorenyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothiophenyl group, an unsubstituted 9,9-dimethylfluorenyl group, or an unsubstituted 9,9-diphenylfluorenyl group. Claim 10 An organic electroluminescence device comprising an anode, a cathode, and a first light-emitting layer included between the anode and the cathode, wherein the first light-emitting layer comprises, as a first host material, a compound described in claim 1. Claim 11 In claim 10, the first light-emitting layer is an organic electroluminescence device further comprising a fluorescent light-emitting compound. Claim 12 An organic electroluminescence device according to claim 11, wherein the singlet energy S1 of the first host material is greater than the singlet energy S1 of the fluorescent emitting compound. Claim 13 In claim 10, the above-mentioned first light-emitting layer is an organic electroluminescence device that does not include a metal complex. Claim 14 An organic electroluminescence device having a hole transport layer between the anode and the first light-emitting layer in claim 10. Claim 15 An organic electroluminescence device having an electron transport layer between the cathode and the first light-emitting layer in claim 10. Claim 16 An organic electroluminescence device according to claim 10, having a second light-emitting layer disposed between the first light-emitting layer and the cathode. Claim 17 In claim 16, the second light-emitting layer is an organic electroluminescence device containing a second compound represented by the following general formula (2) as a second host material. (In the above general formula (2), R 201 ~R 208 Each independently consists of a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted C1–50 haloalkyl group, a substituted or unsubstituted C2–50 alkenyl group, a substituted or unsubstituted C2–50 alkynyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, -Si(R 901 )(R 902 )(R 903 The one indicated by ),-O-(R 904 The element indicated by ),-S-(R 905 The unit represented by ), -N(R 906 )(R 907 A group represented by ), a substituted or unsubstituted aralkyl group with 7–50 carbon atoms, -C(=O)R 801 The one indicated by, -COOR 802 A group represented by, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming complex circulating group having 5 to 50 atoms, and L 201 and L 202 Each is independently a single-bonded, substituted, or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a divalent complex ring-forming group having 5 to 50 atoms, and Ar 201 and Ar 202 Each is independently a cyclic aryl group having 6 to 50 carbon atoms, either substituted or unsubstituted, or a cyclic heterocyclic group having 5 to 50 atoms, either substituted or unsubstituted.) (Among the second compound above, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each is independently a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, a substituted or unsubstituted ring-forming C6–50 aryl group, or a substituted or unsubstituted ring-forming heterocyclic group with 5–50 atoms, and R 901 If this plural exists, the plural R 901 are identical or different from each other, R 902 If there are multiple instances of , multiple R 902 are identical or different from each other, R 903 If this plural exists, the plural R 903 are identical or different from each other, R 904 If there are multiple instances of , multiple R 904 are identical or different from each other, R 905 If there are multiple instances of , multiple R 905 are identical or different from each other, R 906 If this plural exists, the plural R 906 are identical or different from each other, R 907 If this plural exists, the plural R 907 are identical or different from each other, R 801 If this plural exists, the plural R 801 are identical or different from each other, R 802 If there are multiple instances of , multiple R 802 are identical or different from each other. Claim 18 An electronic device equipped with an organic electroluminescence element as described in paragraph 10. Claim 19 A compound represented by the following general formula (1), (2) or (3). (In the above general formulas (1) to (3), R 111 ~R 119 and R 211 ~R 219 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 carbon atoms, a group represented by -Si(Rx)(Ry)(Rz), a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms, and in -Si(Rx)(Ry)(Rz), Rx, Ry, and Rz are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and in the above general formula (1), R 11 and R 12 of, R 13 and R 14 of, R 21 and R 22 of, R 23 and R 24 One or more groups comprising groups of members combine with each other to form a substituted or non-substituted single ring, combine with each other to form a substituted or non-substituted condensed ring, or do not combine with each other and do not form the said substituted or non-substituted single ring, and also do not form the said substituted or non-substituted condensed ring R 11 , R 13 , R 21 and R 23 R is each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, or a group represented by the following general formula (4), and does not form the substituted or unsubstituted single ring and also does not form the substituted or unsubstituted condensed ring. 12 , R 14 , R 22 and R 24 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, or a group represented by the following general formula (4), provided that R 11 ~R 14 and R 21 ~R 24 Among them, at least one is not a hydrogen atom, and in the above general formulas (2) to (3), R 31 ~R 33 , R 41 ~R 43 , R 51 ~R 54 and R 61 ~R 64 R, comprising two or more adjacent groups, wherein one or more groups combine with each other to form a substituted or non-substituted single ring, combine with each other to form a substituted or non-substituted condensed ring, or do not combine with each other to form the said substituted or non-substituted single ring, and also do not form the said substituted or non-substituted condensed ring. 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 and R 61 ~R 64 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, or a group represented by the following general formula (4), provided that R 31 ~R 34 and R 41 ~R 44 Of these, at least one is not a hydrogen atom, and R 51 ~R 54 and R 61 ~R 64 Among them, at least one is not a hydrogen atom, and R in a compound represented by the above general formula (1). 11 and R 13 The group and R 21 and R 23 The keys of are different keys, or R 12 and R 14 The group and R 22 and R 24 The groups of are different from each other, and R in the compound represented by the above general formula (2). 31 and R 41 The group of, and R 32 and R 42 of, R 33 and R 43 The group of, and R 34 and R 44 Among the groups, at least one group is different from each other, and R in the compound represented by the above general formula (3). 51 and R 61 The group of, and R 52 and R 62 of, R 53 and R 63 The group of, and R 54 and R 64 At least one of the groups is different from the others.) (In the above general formula (4), X 13 Silver oxygen atoms, sulfur atoms, or NR 319 is,R 311 ~R 318 R, comprising two or more adjacent groups, wherein one or more groups combine with each other to form a substituted or non-substituted single ring, combine with each other to form a substituted or non-substituted condensed ring, or do not combine with each other to form the said substituted or non-substituted single ring, and also do not form the said substituted or non-substituted condensed ring. 311 ~R 319 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group, and does not form the substituted or unsubstituted monocyclic group, and also the substituted or unsubstituted R that does not form a condensation ring 311 ~R 319 One of them is R 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 and R 61 ~R 64 It is a single bond that bonds to at least one of the above general formulas (1) to (3), R 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 , R 61 ~R 64 , R 111 ~R 119 , R 211 ~R 219 and R 311 ~R 319 In the case of "substituted or unsubstituted," "substitution" refers to being independently substituted by an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted terphenyl group, an unsubstituted naphthyl group, an unsubstituted anthryl group, an unsubstituted phenanthryl group, an unsubstituted chrysenyl group, an unsubstituted triphenylenyl group, an unsubstituted fluorenyl group, an unsubstituted 9,9'-spirobifluorenyl group, an unsubstituted 9,9-dimethylfluorenyl group, or an unsubstituted 9,9-diphenylfluorenyl group. Claim 20 In Paragraph 19, R 111 ~R 119 and R 211 ~R 219 A compound in which each is independently a hydrogen atom, a substituted or unsubstituted C1-18 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group. Claim 21 In Paragraph 19, R 11 and R 12 of, R 13 and R 14 of, R 21 and R 22 of, R 23 and R 24 One or more groups consisting of groups of do not combine with each other, R 31 ~R 33 , R 41 ~R 43 , R 51 ~R 54 and R 61 ~R 64 A compound in which at least one of two or more adjacent groups does not bond with each other. Claim 22 In paragraph 19, a compound represented by the following general formula (1-1), (2-1) or (3-1). (In the above general formulas (1-1), (2-1) and (3-1), R 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 , R 61 ~R 64 R in the above general formulas (1) to (3) is independently 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 , R 61 ~R 64 It has the same meaning as.) Claim 23 In Paragraph 19, R 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 and R 61 ~R 64 Each is independently a hydrogen atom, a substituted or unsubstituted C1–C8 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, provided that R 12 , R 14 , R 22 and R 24 is a compound that is not a substituted or unsubstituted phenyl group. Claim 24 In Paragraph 19, R 11 and R 12 of, R 13 and R 14 of, R 21 and R 22 of, R 23 and R 24 One or more groups of groups consisting of combine with each other to form a substituted or non-substituted single ring or a substituted or non-substituted condensed ring, and R 31 ~R 33 , R 41 ~R 43 , R 51 ~R 54 and R 61 ~R 64 A compound in which one or more of two or more adjacent groups combine to form a substituted or unsubstituted single ring or a substituted or unsubstituted condensed ring. Claim 25 A compound represented by any one of the following general formulas (1-2), (2-2) to (2-3) and (3-2) to (3-4) in paragraph 24. (In the above general formulas (1-2), (2-2) to (2-3) and (3-2) to (3-4), R 13 ~R 14 , R 21 ~R 22 , R 31 , R 33 , R 34 , R 41 , R 43 , R 44 , R 51 ~R 54 and R 61 ~R 64 R in the above general formulas (1) to (3) is independently 13 ~R 14 , R 21 ~R 22 , R 31 , R 33 , R 34 , R 41 , R 43 , R 44 , R 51 ~R 54 and R 61 ~R 64 It has the same meaning as, and R 301 ~R 308 Each is independently R in the above general formulas (1) to (3). 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 and R 61 ~R 64 It has the same meaning as.) Claim 26 In paragraph 25, R 13 ~R 14 , R 21 ~R 22 , R 31 , R 33 , R 34 , R 41 , R 43 , R 44 , R 51 ~R 54 , R 61 ~R 64 and R 301 ~R 308 Each is independently a hydrogen atom, a substituted or unsubstituted C1–C8 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, provided that R 14 and R 22 is a compound that is not a substituted or unsubstituted phenyl group. Claim 27 In Paragraph 19, R 11 ~R 14 , R 21 ~R 24 , R 31 ~R 34 , R 41 ~R 44 , R 51 ~R 54 , R 61 ~R 64 , R 111 ~R 119 , R 211 ~R 219 and R 301 ~R 308 A compound in which, in the case of “substituted or unsubstituted,” “substituted” means each independently substituted by an unsubstituted C1-C8 alkyl group, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, an unsubstituted fluorenyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothiophenyl group, an unsubstituted 9,9-dimethylfluorenyl group, or an unsubstituted 9,9-diphenylfluorenyl group. Claim 28 An organic electroluminescence device comprising an anode, a cathode, and a first light-emitting layer included between the anode and the cathode, wherein the first light-emitting layer comprises, as a first host material, a compound described in claim 19. Claim 29 In claim 28, the above-mentioned first light-emitting layer further comprises an organic electroluminescence device comprising a fluorescent light-emitting compound. Claim 30 In claim 29, an organic electroluminescence device in which the singlet energy S1 of the first host material is greater than the singlet energy S1 of the fluorescently emitting compound. S1(M2)>S1(M1)… (Equation 1) Claim 31 In claim 28, the above-mentioned first light-emitting layer is an organic electroluminescence device that does not include a metal complex. Claim 32 An organic electroluminescence device having a hole transport layer between the anode and the first light-emitting layer in claim 28. Claim 33 An organic electroluminescence device having an electron transport layer between the cathode and the first light-emitting layer in claim 28. Claim 34 An electronic device equipped with an organic electroluminescence element as described in paragraph 28. Claim 35 An organic electroluminescence device according to claim 28, having a second light-emitting layer disposed between the first light-emitting layer and the cathode. Claim 36 In claim 35, the second light-emitting layer is an organic electroluminescence device containing a second compound represented by the following general formula (2) as a second host material. (In the above general formula (2), R 201 ~R 208 Each independently consists of a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted C1–50 haloalkyl group, a substituted or unsubstituted C2–50 alkenyl group, a substituted or unsubstituted C2–50 alkynyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, -Si(R 901 )(R 902 )(R 903 The one indicated by ),-O-(R 904 The element indicated by ),-S-(R 905 The unit represented by ), -N(R 906 )(R 907 A group represented by ), a substituted or unsubstituted aralkyl group with 7–50 carbon atoms, -C(=O)R 801 The one indicated by, -COOR 802 A group represented by, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming complex circulating group having 5 to 50 atoms, and L 201 and L 202 Each is independently a single-bonded, substituted, or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a divalent complex ring-forming group having 5 to 50 atoms, and Ar 201 and Ar 202 Each is independently a cyclic aryl group having 6 to 50 carbon atoms, either substituted or unsubstituted, or a cyclic heterocyclic group having 5 to 50 atoms, either substituted or unsubstituted.) (Among the second compound above, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each is independently a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, a substituted or unsubstituted ring-forming C6–50 aryl group, or a substituted or unsubstituted ring-forming heterocyclic group with 5–50 atoms, and R 901 If this plural exists, the plural R 901 are identical or different from each other, R 902 If there are multiple instances of , multiple R 902 are identical or different from each other, R 903 If this plural exists, the plural R 903 are identical or different from each other, R 904 If there are multiple instances of , multiple R 904 are identical or different from each other, R 905 If there are multiple instances of , multiple R 905 are identical or different from each other, R 906 If this plural exists, the plural R 906 are identical or different from each other, R 907 If this plural exists, the plural R 907 are identical or different from each other, R 801 If this plural exists, the plural R 801 are identical or different from each other, R 802 If there are multiple instances of , multiple R 802 are identical or different from each other. Claim 37 In claim 16, the second light-emitting layer comprises an organic electroluminescence device comprising a compound that emits light with a main peak wavelength of 430 nm or more and 480 nm or less. Claim 38 In claim 35, the second light-emitting layer comprises an organic electroluminescence device comprising a compound that emits light with a main peak wavelength of 430 nm or more and 480 nm or less. Claim 39 In claim 16, the organic electroluminescence device comprising the first light-emitting layer and the second light-emitting layer having the same fluorescent light-emitting compound. Claim 40 In claim 35, the first light-emitting layer and the second light-emitting layer are organic electroluminescent devices comprising the same fluorescent light-emitting compound. Claim 41 delete
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