Organic electroluminescent elements and electronic devices
By employing a combination of light-emitting layer materials with a specific structure in organic electroluminescent elements, and using compounds of general formula (1) and general formula (2) as the main materials for the directly connected first and second light-emitting layers, the problems of insufficient performance and luminous efficiency in the prior art are solved, and a more efficient luminous effect is achieved.
Patent Information
- Application Number
- CN202080064202.6
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2019-12-27
- Filing Date
- 2020-09-11
- Publication Date
- 2025-10-31
- Estimated Expiration
- 2040-09-11
AI Technical Summary
The performance and luminous efficiency of existing organic electroluminescent devices need to be improved, especially in the selection of luminescent layer materials, which have not been fully optimized.
The first and second light-emitting layer materials with specific structures are used. The first and second light-emitting layers are disposed between the anode and the cathode and are directly connected. The compounds represented by general formulas (1) and (2) are used as the host materials to improve the luminous efficiency.
By optimizing the combination of light-emitting layer materials, the performance and luminous efficiency of organic electroluminescent elements have been significantly improved, meeting the requirements for improving brightness, color, driving voltage, and lifespan.
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Figure CN114402455B_ABST
Abstract
Description
Technical Field
[0001] This invention relates to organic electroluminescent elements and electronic devices. Background Technology
[0002] Organic electroluminescent devices (hereinafter sometimes referred to as "organic EL devices") are used in full-color displays for mobile phones and televisions. When a voltage is applied to an organic EL device, holes are injected from the anode into the emitting layer, and electrons are injected from the cathode into the emitting layer. Then, the holes injected into the emitting layer recombine with the electrons to form excitons. At this time, according to the statistical law of electron spin, singlet excitons are generated at a ratio of 25%, and triplet excitons are generated at a ratio of 75%.
[0003] To improve the performance of organic EL devices, various studies have been conducted on compounds used in organic EL devices (see, for example, Patent Documents 1-6). Examples of the performance characteristics of organic EL devices include, for instance, brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifetime.
[0004] Existing technical documents
[0005] Patent documents
[0006] Patent Document 1: Japanese Patent Application Publication No. 2013-157552
[0007] Patent Document 2: International Publication No. 2004 / 018587
[0008] Patent Document 3: International Publication No. 2005 / 115950
[0009] Patent Document 4: International Publication No. 2011 / 077691
[0010] Patent Document 5: Japanese Patent Application Publication No. 2018-125504
[0011] Patent Document 6: U.S. Patent Application Publication No. 2019 / 280209 Summary of the Invention
[0012] The problem the invention aims to solve
[0013] One object of the present invention is to provide an organic electroluminescent element with improved performance. Another object of the present invention is to provide an organic electroluminescent element with improved luminous efficiency, and an electronic device incorporating the organic electroluminescent element.
[0014] means for solving problems
[0015] According to one aspect of the present invention, an organic electroluminescent element is provided, which has 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. The first light-emitting layer contains a first compound having at least one group represented by the following general formula (11) and represented by the following general formula (1) as a first host material. The second light-emitting layer contains a second compound represented by the following general formula (2) as a second host material. The first light-emitting layer and the second light-emitting layer are directly connected.
[0016]
Chemical Formula 1
[0017]
[0018] (In the above general formula (1),
[0019] R 101 ~R 110 Each independently
[0020] hydrogen atom,
[0021] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0022] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0023] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0024] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0025] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0026] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0027] -O-(R 904 The groups shown in the figure,
[0028] -S-(R 905 The groups shown in the figure,
[0029] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0030] -C(=O)R 801 The groups shown
[0031] -COOR 802 The groups shown
[0032] Halogen atoms,
[0033] cyano,
[0034] Nitro,
[0035] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[0036] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[0037] The groups represented by the above general formula (11),
[0038] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11) above.
[0039] When there are multiple groups represented by the above general formula (11), the multiple groups represented by the above general formula (11) may be the same as or different from each other.
[0040] L 101 for
[0041] single bond,
[0042] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[0043] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0044] Ar 101 for
[0045] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0046] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0047] mx is 0, 1, 2, 3, 4, or 5.
[0048] In L 101 When there are more than two, more than two L 101 They are the same or different.
[0049] In Ar 101 In the case of two or more Ar, two or more Ar 101 They are the same or different.
[0050] In the above general formula (11), * indicates the bonding position with the pyrene ring in the above general formula (1).
[0051] [Chemical Formula 2]
[0052]
[0053] (In the above general formula (2),)
[0054] R 201 ~R 208 Each independently
[0055] hydrogen atom,
[0056] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0057] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0058] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0059] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0060] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0061] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0062] -O-(R 904 The groups shown in the figure,
[0063] -S-(R 905 The groups shown in the figure,
[0064] -N(R 906 (R) 907 The groups shown in the figure,
[0065] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0066] -C(=O)R 801 The groups shown
[0067] -COOR 802 The groups shown
[0068] Halogen atoms,
[0069] cyano,
[0070] Nitro,
[0071] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0072] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0073] L 201 and L 202 Each independently
[0074] single bond,
[0075] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[0076] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0077] Ar 201 and Ar 202 Each independently
[0078] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0079] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[0080] (In the first compound represented by the above general formula (1) 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
[0081] hydrogen atom,
[0082] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0083] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0084] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0085] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0086] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[0087] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[0088] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.
[0089] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
[0090] In R 905 In the case of multiple Rs, multiple Rs905 They are the same or different.
[0091] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.
[0092] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.
[0093] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[0094] In R 802 In the case of multiple Rs, multiple Rs 802 (They may be the same or different.)
[0095] According to one aspect of the present invention, an organic electroluminescent element is provided, which has 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. The first light-emitting layer contains a first compound having at least one group represented by the following general formula (11) and represented by the following general formula (1) as a first host material. The second light-emitting layer contains a second compound represented by the following general formula (2) as a second host material. The first light-emitting layer and the second light-emitting layer are directly connected.
[0096]
Chemical Formula 3
[0097]
[0098] (In the above general formula (1),
[0099] R 101 ~R 110 Each independently
[0100] hydrogen atom,
[0101] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0102] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0103] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0104] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0105] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0106] -Si(R 901 (R)902 (R) 903 The groups shown in the figure,
[0107] -O-(R 904 The groups shown in the figure,
[0108] -S-(R 905 The groups shown in the figure,
[0109] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0110] -C(=O)R 801 The groups shown
[0111] -COOR 802 The groups shown
[0112] Halogen atoms,
[0113] cyano,
[0114] Nitro,
[0115] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0116] The groups represented by the above general formula (11),
[0117] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11) above.
[0118] When there are multiple groups represented by the above general formula (11), the multiple groups represented by the above general formula (11) may be the same as or different from each other.
[0119] L 101 for
[0120] single key or
[0121] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms in a cyclic structure.
[0122] Ar 101 For substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic structure,
[0123] mx is 0, 1, 2, 3, 4, or 5.
[0124] Ar 101 It is neither a substituted nor an unsubstituted pyrene group.
[0125] L 101 It is neither a replaced nor unreplaced pyrene group.
[0126] R, which is not a group represented by the above general formula (11) 101 ~R110 The substituted or unsubstituted aryl group with 6 to 50 carbon atoms is not a substituted or unsubstituted pyrene group.
[0127] In L 101 When there are more than two, more than two L 101 They are the same or different.
[0128] In Ar 101 In the case of two or more Ar, two or more Ar 101 They are the same or different.
[0129] In the above general formula (11), * indicates the bonding position with the pyrene ring in the above general formula (1).
[0130] According to one aspect of the present invention, an organic electroluminescent element is provided, which has 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. The first light-emitting layer contains a first compound having at least two groups represented by the following general formula (11) and represented by the following general formula (1) as a first host material. The second light-emitting layer contains a second compound represented by the following general formula (2) as a second host material. The first light-emitting layer and the second light-emitting layer are directly connected.
[0131] [Chemical Formula 4]
[0132]
[0133] (In the above general formula (1),
[0134] R 101 ~R 110 Each independently
[0135] hydrogen atom,
[0136] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0137] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0138] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0139] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0140] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0141] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0142] -O-(R 904 The groups shown in the figure,
[0143] -S-(R 905 The groups shown in the figure,
[0144] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0145] -C(=O)R 801 The groups shown
[0146] -COOR 802 The groups shown
[0147] Halogen atoms,
[0148] cyano,
[0149] Nitro, or
[0150] The groups represented by the above general formula (11),
[0151] Among them, R 101 ~R 110 Two or more of them are groups represented by the general formula (11) above.
[0152] When there are multiple groups represented by the above general formula (11), the multiple groups represented by the above general formula (11) may be the same as or different from each other.
[0153] L 101 It is a single key.
[0154] Ar 101 It is a heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[0155] mx is 0
[0156] In Ar 101 In the case of two or more Ar, two or more Ar 101 They are the same or different.
[0157] In the above general formula (11), * indicates the bonding position with the pyrene ring in the above general formula (1).
[0158] According to one aspect of the present invention, an organic electroluminescent element is provided, which has 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. The first light-emitting layer contains a first compound having at least one group represented by the following general formula (11) and represented by the following general formula (1) as a first host material. The second light-emitting layer contains a second compound represented by the following general formula (2) as a second host material. The first light-emitting layer and the second light-emitting layer are directly connected.
[0159] [Chemical Formula 5]
[0160]
[0161] (In the above general formula (1),
[0162] R 101 ~R 110 Each independently
[0163] hydrogen atom,
[0164] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0165] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0166] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0167] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0168] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0169] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0170] -O-(R 904 The groups shown in the figure,
[0171] -S-(R 905 The groups shown in the figure,
[0172] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0173] -C(=O)R 801 The groups shown
[0174] -COOR 802 The groups shown
[0175] Halogen atoms,
[0176] cyano,
[0177] Nitro,
[0178] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[0179] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[0180] The groups represented by the above general formula (11),
[0181] Among them, R101 ~R 110 At least one of them is a group represented by the general formula (11) above.
[0182] When there are multiple groups represented by the above general formula (11), the multiple groups represented by the above general formula (11) may be the same as or different from each other.
[0183] L 101 It is a divalent heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[0184] Ar 101 It is a heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[0185] mx is 1, 2, 3, 4 or 5.
[0186] R, which is not a group represented by the above general formula (11) 101 ~R 110 The substituted or unsubstituted aryl group with 6 to 50 carbon atoms is not a substituted or unsubstituted pyrene group.
[0187] In L 101 When there are more than two, more than two L 101 They are the same or different.
[0188] In Ar 101 In the case of two or more Ar, two or more Ar 101 They are the same or different.
[0189] In the above general formula (11), * indicates the bonding position with the pyrene ring in the above general formula (1).
[0190] According to one aspect of the present invention, an organic electroluminescent element is provided, which has 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. The first light-emitting layer contains a first compound having at least one group represented by the following general formula (11) and represented by the following general formula (1) as a first host material. The second light-emitting layer contains a second compound represented by the following general formula (2) as a second host material. The first light-emitting layer and the second light-emitting layer are directly connected.
[0191]
Chemical Formula 6
[0192]
[0193] (In the above general formula (1),
[0194] R 101 ~R 110 Each independently
[0195] hydrogen atom,
[0196] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0197] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0198] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0199] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0200] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0201] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0202] -O-(R 904 The groups shown in the figure,
[0203] -S-(R 905 The groups shown in the figure,
[0204] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0205] -C(=O)R 801 The groups shown
[0206] -COOR 802 The groups shown
[0207] Halogen atoms,
[0208] cyano,
[0209] Nitro,
[0210] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[0211] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[0212] The groups represented by the above general formula (11),
[0213] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11) above.
[0214] Among them, R 101 ~R 110 At least one of them is a heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms.
[0215] When there are multiple groups represented by the above general formula (11), the multiple groups represented by the above general formula (11) may be the same as or different from each other.
[0216] L 101 for
[0217] single key or
[0218] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms in a cyclic structure.
[0219] Ar 101 For substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic structure,
[0220] mx is 0, 1, 2, 3, 4, or 5.
[0221] Ar 101 It is neither a substituted nor an unsubstituted pyrene group.
[0222] L 101 It is neither a replaced nor unreplaced pyrene group.
[0223] R, which is not a group represented by the above general formula (11) 101 ~R 110 The substituted or unsubstituted aryl group with 6 to 50 carbon atoms is not a substituted or unsubstituted pyrene group.
[0224] In L 101 When there are more than two, more than two L 101 They are the same or different.
[0225] In Ar 101 In the case of two or more Ar, two or more Ar 101 They are the same or different.
[0226] In the above general formula (11), * indicates the bonding position with the pyrene ring in the above general formula (1).
[0227] According to one aspect of the present invention, an organic electroluminescent element is provided, which has 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. The first light-emitting layer contains a first compound having at least one group represented by the following general formula (11) and represented by the following general formula (1) as a first host material. The second light-emitting layer contains a second compound represented by the following general formula (2) as a second host material. The first light-emitting layer and the second light-emitting layer are directly connected.
[0228] [Chemical Formula 7]
[0229]
[0230] (In the above general formula (1),
[0231] R 101 ~R 110 Each independently
[0232] hydrogen atom,
[0233] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0234] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0235] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0236] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0237] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0238] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0239] -O-(R 904 The groups shown in the figure,
[0240] -S-(R 905 The groups shown in the figure,
[0241] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0242] -C(=O)R 801 The groups shown
[0243] -COOR 802 The groups shown
[0244] Halogen atoms,
[0245] cyano,
[0246] Nitro,
[0247] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[0248] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[0249] The groups represented by the above general formula (11),
[0250] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11) above.
[0251] When there are multiple groups represented by the above general formula (11), the multiple groups represented by the above general formula (11) may be the same as or different from each other.
[0252] L 101 For substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic structure,
[0253] Ar 101 It is a heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[0254] mx is 1, 2, 3, 4 or 5.
[0255] L 101 It is neither a replaced nor unreplaced pyrene group.
[0256] R, which is not a group represented by the above general formula (11) 101 ~R 110 The substituted or unsubstituted aryl group with 6 to 50 carbon atoms is not a substituted or unsubstituted pyrene group.
[0257] In L 101 When there are more than two, more than two L 101 They are the same or different.
[0258] In Ar 101 In the case of two or more Ar, two or more Ar 101 They are the same or different.
[0259] In the above general formula (11), * indicates the bonding position with the pyrene ring in the above general formula (1).
[0260] According to one aspect of the present invention, an organic electroluminescent element is provided, which has 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. The first light-emitting layer contains a first compound having at least one group represented by the following general formula (11) and represented by the following general formula (1) as a first host material. The second light-emitting layer contains a second compound represented by the following general formula (2) as a second host material. The first light-emitting layer and the second light-emitting layer are directly connected.
[0261] [Chemical Formula 8]
[0262]
[0263] (In the above general formula (1),
[0264] R 101 ~R 110 Each independently
[0265] hydrogen atom,
[0266] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0267] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0268] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0269] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0270] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0271] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0272] -O-(R 904 The groups shown in the figure,
[0273] -S-(R 905 The groups shown in the figure,
[0274] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0275] -C(=O)R 801 The groups shown
[0276] -COOR 802 The groups shown
[0277] Halogen atoms,
[0278] cyano,
[0279] Nitro,
[0280] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[0281] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[0282] The groups represented by the above general formula (11),
[0283] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11) above.
[0284] When there are multiple groups represented by the above general formula (11), the multiple groups represented by the above general formula (11) may be the same as or different from each other.
[0285] L 101 It is a divalent heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[0286] Ar 101 For substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic structure,
[0287] mx is 1, 2, 3, 4 or 5.
[0288] Ar 101 It is neither a substituted nor an unsubstituted pyrene group.
[0289] R, which is not a group represented by the above general formula (11) 101 ~R 110 The substituted or unsubstituted aryl group with 6 to 50 carbon atoms is not a substituted or unsubstituted pyrene group.
[0290] In L 101 When there are more than two, more than two L 101 They are the same or different.
[0291] In Ar 101 In the case of two or more Ar, two or more Ar 101 They are the same or different.
[0292] In the above general formula (11), * indicates the bonding position with the pyrene ring in the above general formula (1).
[0293] According to one aspect of the present invention, an organic electroluminescent element is provided, which has 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. The first light-emitting layer contains a first compound having at least one group represented by the following general formula (11A) and represented by the following general formula (1) as a first host material. The second light-emitting layer contains a second compound represented by the following general formula (2) as a second host material. The first light-emitting layer and the second light-emitting layer are directly connected.
[0294] [Chemical Formula 9]
[0295]
[0296] (In the above general formula (1),
[0297] R 101 ~R 110 Each independently
[0298] hydrogen atom,
[0299] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0300] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0301] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0302] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0303] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0304] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0305] -O-(R 904 The groups shown in the figure,
[0306] -S-(R 905 The groups shown in the figure,
[0307] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0308] -C(=O)R 801 The groups shown
[0309] -COOR 802 The groups shown
[0310] Halogen atoms,
[0311] cyano,
[0312] Nitro,
[0313] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[0314] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[0315] The groups represented by the above general formula (11A),
[0316] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11A) above.
[0317] When multiple groups represented by the above general formula (11A) are present, the multiple groups represented by the above general formula (11A) may be the same as or different from each other.
[0318] X A It consists of oxygen or sulfur atoms.
[0319] R 131 R 133 and R 134 One or more of the groups consisting of two or more adjacent elements.
[0320] They bond together to form substituted or unsubstituted monocyclic rings, or
[0321] They bond together to form substituted or unsubstituted fused rings, or
[0322] They do not bond with each other.
[0323] R 135 ~R 138 R and R that do not form the aforementioned substituted or unsubstituted monocyclic rings and do not form the aforementioned substituted or unsubstituted fused rings. 131 R 133 and R 134 Each independently
[0324] hydrogen atom,
[0325] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0326] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0327] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0328] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0329] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0330] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0331] -O-(R 904 The groups shown in the figure,
[0332] -S-(R 905 The groups shown in the figure,
[0333] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0334] -C(=O)R 801 The groups shown
[0335] -COOR 802 The groups shown
[0336] Halogen atoms,
[0337] cyano,
[0338] Nitro,
[0339] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0340] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0341] In the above general formula (11A), * indicates the bonding position with the pyrene ring in the above general formula (1).
[0342] According to one aspect of the present invention, an organic electroluminescent element is provided, which has 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. The first light-emitting layer contains a first compound having at least one group represented by the following general formula (11B) and represented by the following general formula (1) as a first host material. The second light-emitting layer contains a second compound represented by the following general formula (2) as a second host material. The first light-emitting layer and the second light-emitting layer are directly connected.
[0343]
Chemical Formula 10
[0344]
[0345] (In the above general formula (1),
[0346] R 101 ~R 110 Each independently
[0347] hydrogen atom,
[0348] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0349] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0350] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0351] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0352] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0353] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0354] -O-(R 904 The groups shown in the figure,
[0355] -S-(R 905 The groups shown in the figure,
[0356] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0357] -C(=O)R 801 The groups shown
[0358] -COOR 802 The groups shown
[0359] Halogen atoms,
[0360] cyano,
[0361] Nitro,
[0362] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[0363] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[0364] The groups represented by the above general formula (11B),
[0365] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11B) above.
[0366] When multiple groups represented by the above general formula (11B) are present, the multiple groups represented by the above general formula (11B) may be the same as or different from each other.
[0367] X A It consists of oxygen or sulfur atoms.
[0368] R 131 R 133 ~R 135 R 138 and R 141 ~R 144 One or more of the groups consisting of two or more adjacent elements.
[0369] They bond together to form substituted or unsubstituted monocyclic rings, or
[0370] They bond together to form substituted or unsubstituted fused rings, or
[0371] They do not bond with each other.
[0372] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 131 R 133 ~R 135 R 138 and R 141 ~R 144 Each independently
[0373] hydrogen atom,
[0374] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0375] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0376] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0377] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0378] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0379] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0380] -O-(R 904 The groups shown in the figure,
[0381] -S-(R 905 The groups shown in the figure,
[0382] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0383] -C(=O)R 801 The groups shown
[0384] -COOR 802 The groups shown
[0385] Halogen atoms,
[0386] cyano,
[0387] Nitro,
[0388] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0389] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0390] Among them, R 135 R 138 and R 141 ~R 144 At least one of them is
[0391] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0392] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0393] In the above general formula (11B), * indicates the bonding position with the pyrene ring in the above general formula (1).
[0394] According to one aspect of the present invention, an organic electroluminescent element is provided, which has 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. The first light-emitting layer contains a first compound having at least one group represented by the following general formula (11C) and represented by the following general formula (1) as a first host material. The second light-emitting layer contains a second compound represented by the following general formula (2) as a second host material. The first light-emitting layer and the second light-emitting layer are directly connected.
[0395]
Chemical Formula 11
[0396]
[0397] (In the above general formula (1),
[0398] R 101 ~R 110 Each independently
[0399] hydrogen atom,
[0400] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0401] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0402] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0403] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0404] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0405] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0406] -O-(R 904 The groups shown in the figure,
[0407] -S-(R 905 The groups shown in the figure,
[0408] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0409] -C(=O)R 801 The groups shown
[0410] -COOR 802 The groups shown
[0411] Halogen atoms,
[0412] cyano,
[0413] Nitro,
[0414] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[0415] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[0416] The groups represented by the above general formula (11C),
[0417] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11C) above.
[0418] When multiple groups represented by the above general formula (11C) are present, the multiple groups represented by the above general formula (11C) may be the same as or different from each other.
[0419] X A It consists of oxygen or sulfur atoms.
[0420] R 131 R 133 R 134 R 137 R 138 and R 141 ~R 144 One or more of the groups consisting of two or more adjacent elements.
[0421] They bond together to form substituted or unsubstituted monocyclic rings, or
[0422] They bond together to form substituted or unsubstituted fused rings, or
[0423] They do not bond with each other.
[0424] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 131 R 133 R 134 R 137 R 138 and R 141 ~R 144 Each independently
[0425] hydrogen atom,
[0426] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0427] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0428] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0429] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0430] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0431] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0432] -O-(R 904 The groups shown in the figure,
[0433] -S-(R 905 The groups shown in the figure,
[0434] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0435] -C(=O)R 801 The groups shown
[0436] -COOR 802 The groups shown
[0437] Halogen atoms,
[0438] cyano,
[0439] Nitro,
[0440] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0441] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0442] In the above general formula (11C), * indicates the bonding position with the pyrene ring in the above general formula (1).
[0443] According to one aspect of the present invention, an organic electroluminescent element is provided, which has 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. The first light-emitting layer contains a first compound having at least one group represented by the following general formula (11D) and represented by the following general formula (1) as a first host material. The second light-emitting layer contains a second compound represented by the following general formula (2) as a second host material. The first light-emitting layer and the second light-emitting layer are directly connected.
[0444]
Chemical Formula 12
[0445]
[0446] (In the above general formula (1),
[0447] R 101 ~R110 Each independently
[0448] hydrogen atom,
[0449] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0450] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0451] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0452] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0453] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0454] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0455] -O-(R 904 The groups shown in the figure,
[0456] -S-(R 905 The groups shown in the figure,
[0457] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0458] -C(=O)R 801 The groups shown
[0459] -COOR 802 The groups shown
[0460] Halogen atoms,
[0461] cyano,
[0462] Nitro,
[0463] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[0464] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[0465] The groups represented by the above general formula (11D),
[0466] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11D) above.
[0467] When multiple groups represented by the above general formula (11D) are present, the multiple groups represented by the above general formula (11D) may be the same as or different from each other.
[0468] X A It consists of oxygen or sulfur atoms.
[0469] R 131 R 133 R 134 R 135 R 136 and R 141 ~R 144 One or more of the groups consisting of two or more adjacent elements.
[0470] They bond together to form substituted or unsubstituted monocyclic rings, or
[0471] They bond together to form substituted or unsubstituted fused rings, or
[0472] They do not bond with each other.
[0473] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 131 R 133 R 134 R 135 R 136 and R 141 ~R 144 Each independently
[0474] hydrogen atom,
[0475] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0476] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0477] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0478] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0479] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0480] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0481] -O-(R 904 The groups shown in the figure,
[0482] -S-(R 905 The groups shown in the figure,
[0483] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0484] -C(=O)R 801 The groups shown
[0485] -COOR 802 The groups shown
[0486] Halogen atoms,
[0487] cyano,
[0488] Nitro,
[0489] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0490] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0491] In the above general formula (11D), * indicates the bonding position with the pyrene ring in the above general formula (1).
[0492] According to one aspect of the present invention, an organic electroluminescent element is provided, which has 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. The first light-emitting layer contains a first compound having at least one group represented by the following general formula (11E) and represented by the following general formula (1) as a first host material. The second light-emitting layer contains a second compound represented by the following general formula (2) as a second host material. The first light-emitting layer and the second light-emitting layer are directly connected.
[0493]
Chemical Formula 13
[0494]
[0495] (In the above general formula (1),
[0496] R 101 ~R 110 Each independently
[0497] hydrogen atom,
[0498] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0499] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0500] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0501] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0502] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0503] -Si(R 901 (R) 902 (R) 903The groups shown in the figure,
[0504] -O-(R 904 The groups shown in the figure,
[0505] -S-(R 905 The groups shown in the figure,
[0506] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0507] -C(=O)R 801 The groups shown
[0508] -COOR 802 The groups shown
[0509] Halogen atoms,
[0510] cyano,
[0511] Nitro,
[0512] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[0513] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[0514] The groups represented by the above general formula (11E),
[0515] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11E) above.
[0516] When multiple groups represented by the above general formula (11E) are present, the multiple groups represented by the above general formula (11E) may be the same as or different from each other.
[0517] X A It consists of oxygen or sulfur atoms.
[0518] R 131 R 133 ~R 135 R 138 and R 141 ~R 144 One or more of the groups consisting of two or more adjacent elements.
[0519] They bond together to form substituted or unsubstituted monocyclic rings, or
[0520] They bond together to form substituted or unsubstituted fused rings, or
[0521] They do not bond with each other.
[0522] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings.131 R 133 ~R 135 R 138 and R 141 ~R 144 Each independently
[0523] hydrogen atom,
[0524] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0525] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0526] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0527] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0528] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0529] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0530] -O-(R 904 The groups shown in the figure,
[0531] -S-(R 905 The groups shown in the figure,
[0532] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0533] -C(=O)R 801 The groups shown
[0534] -COOR 802 The groups shown
[0535] Halogen atoms,
[0536] cyano,
[0537] Nitro,
[0538] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0539] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0540] L 101 for
[0541] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[0542] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0543] mx is 1, 2, 3, 4 or 5.
[0544] In L 101 When there are more than two, more than two L 101 They are the same or different.
[0545] In the above general formula (11E), * indicates the bonding position with the pyrene ring in the above general formula (1).
[0546] According to one aspect of the present invention, an electronic device is provided, wherein the organic electroluminescent element described above is included.
[0547] According to one aspect of the present invention, an organic electroluminescent element with improved performance can be provided. Furthermore, according to another aspect of the present invention, an organic electroluminescent element with improved luminous efficiency can be provided. Additionally, according to another aspect of the present invention, an electronic device incorporating the organic electroluminescent element can be provided. Attached Figure Description
[0548] Figure 1 This is a diagram illustrating the general configuration of an example of an organic electroluminescent element according to one embodiment of the present invention. Detailed Implementation
[0549] "definition]
[0550] In this specification, a hydrogen atom means an isotope containing different numbers of neutrons, namely protium, deuterium, and tritium.
[0551] In this specification, the chemical structural formula does not explicitly show that the bonding positions of symbols such as "R" and "D" representing deuterium atoms are set to be bonded to hydrogen atoms, i.e., protium atoms, deuterium atoms, or tritium atoms.
[0552] In this specification, the number of carbon atoms forming a ring refers to the number of carbon atoms in the ring itself of a compound whose atoms are bonded in a ring (e.g., monocyclic compounds, fused-ring compounds, bridged-ring compounds, carbocyclic compounds, and heterocyclic compounds). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of carbon atoms forming the ring. The term "number of carbon atoms forming a ring" is used as described below unless otherwise specified. For example, the number of carbon atoms forming a ring is 6 for a benzene ring, 10 for a naphthalene ring, 5 for a pyridine ring, and 4 for a furan ring. Additionally, for example, the number of carbon atoms forming a ring is 13 for 9,9-diphenylfluoreneyl and 25 for 9,9'-spirobifluoreneyl.
[0553] Furthermore, when a benzene ring is substituted with an alkyl group, the carbon number of the alkyl group is not included in the number of carbon atoms in the ring-forming process of the benzene ring. Therefore, the number of carbon atoms in the cyclic benzene ring substituted with an alkyl group is 6. Similarly, when a naphthalene ring is substituted with an alkyl group, the carbon number of the alkyl group is not included in the number of carbon atoms in the ring-forming process of the naphthalene ring. Therefore, the number of carbon atoms in the cyclic naphthalene ring substituted with an alkyl group is 10.
[0554] In this specification, the number of cyclic atoms refers to the number of atoms constituting the ring itself in compounds (e.g., monocyclic compounds, fused-ring compounds, bridged-ring compounds, carbocyclic compounds, and heterocyclic compounds) where atoms are bonded in a ring structure (e.g., monocyclic, fused-ring, and aggregated-ring). Atoms that do not constitute a ring (e.g., hydrogen atoms that end the bonds of the ring-forming atoms) and atoms contained in substituents when the ring is substituted are not included in the number of cyclic atoms. The term "number of cyclic atoms" as used below is the same unless otherwise stated. For example, the number of cyclic atoms in a pyridine ring is 6, in a quinazoline ring it is 10, and in a furan ring it is 5. For example, the number of hydrogen atoms bonded to the pyridine ring or atoms constituting substituents are not included in the number of cyclic atoms in pyridine. Therefore, the number of cyclic atoms in a pyridine ring bonded with hydrogen atoms or substituents is 6. Furthermore, hydrogen atoms bonded to the carbon atoms of the quinazoline ring, or atoms constituting substituents, are not included in the number of cyclic atoms of the quinazoline ring. Therefore, the number of cyclic atoms in a quinazoline ring with bonded hydrogen atoms or substituents is 10.
[0555] In this specification, the phrase "ZZ group with substituted or unsubstituted carbon numbers of XX to YY" indicates the number of carbons when the ZZ group is unsubstituted; the number of carbons in substituents is not included. Here, "YY" is greater than "XX," where "XX" refers to an integer greater than 1, and "YY" refers to an integer greater than 2.
[0556] In this specification, the phrase "ZZ group with substituted or unsubstituted atoms of XX to YY" refers to the number of atoms when the ZZ group is unsubstituted, excluding the number of atoms of substituents when substitution has occurred. Here, "YY" is greater than "XX", where "XX" is an integer greater than or equal to 1, and "YY" is an integer greater than or equal to 2.
[0557] In this specification, "unsubstituted ZZ group" means "substituted or unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".
[0558] In this specification, "unsubstituted" when referred to as "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group has not been substituted with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.
[0559] Furthermore, in this specification, "substitution" when expressed as "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group have been replaced by a substituent. Similarly, "substitution" when expressed as "BB group substituted by AA group" also means that one or more hydrogen atoms in the BB group have been replaced by an AA group.
[0560] Substituents described in this specification
[0561] The substituents described in this specification are explained below.
[0562] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted aryl group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.
[0563] Unless otherwise stated in this specification, the number of cyclic atoms in the "unsubstituted heterocyclic group" is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.
[0564] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.
[0565] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkenyl group" is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.
[0566] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkynyl group" is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.
[0567] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted cycloalkyl group" is 3 to 50, preferably 3 to 20, and more preferably 3 to 6.
[0568] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted aryl group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.
[0569] Unless otherwise specified in this specification, the number of cyclic atoms in the "unsubstituted divalent heterocyclic group" is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.
[0570] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkylene group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.
[0571] • "Substituted or unsubstituted aryl groups"
[0572] Specific examples of "substituted or unsubstituted aryl" as described in this specification (specific example group G1) include unsubstituted aryl (specific example group G1A) and substituted aryl (specific example group G1B), etc. (Here, unsubstituted aryl refers to the case where "substituted or unsubstituted aryl" is "unsubstituted aryl", and substituted aryl refers to the case where "substituted or unsubstituted aryl" is "substituted aryl".) In this specification, when referred to only as "aryl", both "unsubstituted aryl" and "substituted aryl" are included.
[0573] "Substituted aryl" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl" group have been substituted with a substituent. Examples of "substituted aryl" include the group in Specific Example Group G1A below in which one or more hydrogen atoms of an "unsubstituted aryl" group have been substituted with a substituent, and the substituted aryl group in Specific Example Group G1B below. It should be noted that the examples of "unsubstituted aryl" and "substituted aryl" listed here are only examples. The "substituted aryl" described in this specification also includes the group in Specific Example Group G1B below in which hydrogen atoms bonded to the carbon atom of the aryl group itself have been further substituted with a substituent, and the group in Specific Example Group G1B below in which hydrogen atoms of the substituent have been further substituted with a substituent.
[0574] • Unsubstituted aryl groups (specific example group G1A):
[0575] Phenyl,
[0576] p-phenyl,
[0577] metaphenyl,
[0578] o-phenyl,
[0579] p-terphenyl-4-yl,
[0580] p-terphenyl-3-yl,
[0581] p-terphenyl-2-yl,
[0582] m-terphenyl-4-yl,
[0583] m-terphenyl-3-yl,
[0584] m-terphenyl-2-yl,
[0585] o-terphenyl-4-yl
[0586] o-terphenyl, 3, yl,
[0587] o-terphenyl, 2, yl,
[0588] 1-Naphthyl,
[0589] 2-Naphthyl,
[0590] anthracene,
[0591] Benzanthracene,
[0592] Fiki,
[0593] Benzphenanthrene,
[0594] Finadenyl,
[0595] Pyrene
[0596] base,
[0597] benzo[a] base,
[0598] Tri-phenylene,
[0599] Benzotrimethylene
[0600] phenylene,
[0601] Pentaphenyl,
[0602] Fluorine
[0603] 9,9'-spirobisfluorene,
[0604] benzo[f]fluorene,
[0605] Dibenzofluorene,
[0606] Fluoranthene base,
[0607] Benzofluoranthyl,
[0608] Perylene and
[0609] The monovalent aryl group is derived by removing one hydrogen atom from the ring structure shown in the following general formulas (TEMP-1) to (TEMP-15).
[0610]
Chemical Formula 14
[0611]
[0612]
Chemical Formula 15
[0613]
[0614] • Substituted aryl groups (specific example group G1B):
[0615] o-Tolyl,
[0616] m-Tolyl,
[0617] p-Tolyl,
[0618] p-Xylyl,
[0619] m-Xylyl,
[0620] o-xylyl,
[0621] p-isopropylphenyl,
[0622] m-Isopropylphenyl,
[0623] o-isopropylphenyl,
[0624] p-tert-butylphenyl,
[0625] m-tert-butylphenyl,
[0626] o-tert-butylphenyl,
[0627] 3,4,5-Trimethylphenyl,
[0628] 9,9-Dimethylfluorenyl,
[0629] 9,9-Diphenylfluorenyl,
[0630] 9,9-bis(4-methylphenyl)fluorenyl,
[0631] 9,9-Bis(4-isopropylphenyl)fluorenyl,
[0632] 9,9-Bis(4-tert-butylphenyl)fluorenyl,
[0633] cyanophenyl,
[0634] Triphenylsilylphenyl
[0635] Trimethylsilylphenyl
[0636] Phenynaphthyl,
[0637] Naphthylphenyl and
[0638] A group derived from the ring structure shown in the above general formulas (TEMP-1) to (TEMP-15) by substitution of one or more hydrogen atoms of a monovalent group with a substituent.
[0639] • "Substituted or unsubstituted heterocyclic groups"
[0640] The term "heterocyclic group" as used in this specification refers to a cyclic group whose cyclic atoms contain at least one heteroatom. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.
[0641] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.
[0642] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.
[0643] Specific examples of "substituted or unsubstituted heterocyclic groups" described in this specification (specific example group G2) include unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B), etc. (Here, unsubstituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group", and substituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group".) In this specification, the term "heterocyclic group" includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group".
[0644] "Substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" have been substituted with a substituent. Specific examples of "substituted heterocyclic groups" include the group in example group G2A below where the hydrogen atoms of the "unsubstituted heterocyclic group" have been substituted, and the example of a substituted heterocyclic group in example group G2B below. It should be noted that the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are only examples. The "substituted heterocyclic groups" described in this specification also include the group in example group G2B where the hydrogen atoms bonded to the cyclic atoms of the heterocyclic group itself have been further substituted with a substituent, and the group in example group G2B where the hydrogen atoms of the substituent have been further substituted with a substituent.
[0645] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1), unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2), unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3), and monovalent heterocyclic groups derived from the ring structures shown in the following general formulas (TEMP-16) to (TEMP-33) by removing one hydrogen atom (specific example group G2A4).
[0646] Specific example group G2B includes, for example, the following: a nitrogen-containing substituted heterocyclic group (specific example group G2B1), an oxygen-containing substituted heterocyclic group (specific example group G2B2), a sulfur-containing substituted heterocyclic group (specific example group G2B3), and a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) have been substituted with a substituent (specific example group G2B4).
[0647] • Unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1):
[0648] pyrrole,
[0649] Imidazole group,
[0650] pyrazolyl,
[0651] Triazole group,
[0652] Tetrazolyl,
[0653] Oxazolyl,
[0654] Isoxazolyl,
[0655] Oxadiazole group,
[0656] Thiazole group,
[0657] Isothiazolyl,
[0658] Thiadiazole group,
[0659] pyridyl,
[0660] pyridazinyl,
[0661] Pyrimidine group,
[0662] Pyrazinyl,
[0663] Triazine group
[0664] Indole,
[0665] Isoindolyl,
[0666] Indazine-based
[0667] Quinazine-based
[0668] Quinoline,
[0669] Isoquinoline,
[0670] Crenoline group
[0671] Phthaloazine
[0672] Quinazolinyl,
[0673] Quinoxaloyl,
[0674] Benzimidazole group,
[0675] Indazole group,
[0676] phenanthroline,
[0677] phenanthridine,
[0678] acridine group,
[0679] Phenazine group,
[0680] Carbazolyl,
[0681] Benzocarbazolyl,
[0682] Morpholinyl,
[0683] phenoxazine group,
[0684] phenothiazine group,
[0685] Azacarbazolyl and diazacarbazolyl.
[0686] • Unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2):
[0687] furanyl,
[0688] Oxazolyl,
[0689] Isoxazolyl,
[0690] Oxadiazole group,
[0691] Xuton base,
[0692] Benzofuranyl,
[0693] Isobenzofuranyl,
[0694] Dibenzofuranyl,
[0695] Naphthobenzofuranyl,
[0696] Benzoxazolyl,
[0697] Benzisoxazole group,
[0698] phenoxazine group,
[0699] Morpholinyl,
[0700] Dinaphthylfuranyl,
[0701] Azadibenzofuranyl,
[0702] diazadibenzofuranyl,
[0703] Azanaphthalenebenzofuranyl and
[0704] Diazanaphthenebenzofuranyl.
[0705] • Unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3):
[0706] Thiophene group
[0707] Thiazole group,
[0708] Isothiazolyl,
[0709] Thiadiazole group,
[0710] benzothienyl
[0711] Isobenzothienyl
[0712] dibenzothienyl
[0713] Naphthobenzothienyl
[0714] Benzothiazolyl,
[0715] Benzisothiazolyl,
[0716] phenothiazine group,
[0717] dinaphthothienyl
[0718] azadibenzothienyl
[0719] diazadibenzothienyl
[0720] azanaphthobenzothienyl and
[0721] diazanaphthobenzothienyl.
[0722] • The monovalent heterocyclic group derived by removing one hydrogen atom from the ring structures shown in the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):
[0723] [Chemical Formula 16]
[0724]
[0725]
Chemical Formula 17
[0726]
[0727] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each can be independently composed of an oxygen atom, a sulfur atom, NH, or CH2. Among them, X... A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH.
[0728] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y AWhen at least one of them is NH or CH2, the monovalent heterocyclic group derived from the ring structure shown in the above general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.
[0729] • Heterocyclic groups containing nitrogen atoms (specific example group G2B1):
[0730] (9-phenyl)carbazole group,
[0731] (9-Biphenyl)carbazolyl,
[0732] (9-Phenyl)phenylcarbazolyl,
[0733] (9-Naphthyl)carbazole,
[0734] Diphenylcarbazole-9-yl,
[0735] Phenylexacarbazole-9-yl,
[0736] Methylbenzimidazole,
[0737] Ethylbenzimidazole,
[0738] Phenylacetyl,
[0739] Biphenyltriazine
[0740] diphenyltriazine group,
[0741] phenylquinazolinyl and
[0742] Biphenylquinazolinyl.
[0743] • Heterocyclic groups containing oxygen atoms (specific example group G2B2):
[0744] Phenyl dibenzofuranyl,
[0745] Methyldibenzofuranyl,
[0746] tert-butyldibenzofuranyl and
[0747] The monovalent residue of [9H-xanton-9,9'-[9H]fluorene].
[0748] • Heterocyclic groups containing sulfur atoms (specific example group G2B3):
[0749] Phenyl dibenzothiophene,
[0750] Methyldibenzothiophene,
[0751] tert-butyldibenzothiophene and
[0752] The monovalent residue of [9H-thiophene-9,9'-[9H]fluorene].
[0753] • Groups derived from the ring structures shown in the above general formulas (TEMP-16) to (TEMP-33) in which one or more hydrogen atoms of a monovalent heterocyclic group have been substituted with substituents (specific example group G2B4):
[0754] The aforementioned "one or more hydrogen atoms of a monovalent heterocyclic group" refers to one or more hydrogen atoms selected from the following: hydrogen atoms bonded to the cyclic carbon atom of the monovalent heterocyclic group, hydrogen atoms bonded to the nitrogen atom when at least one of XA and YA is NH, and hydrogen atoms of the methylene group when one of XA and YA is CH2.
[0755] • "Substituted or unsubstituted alkyl groups"
[0756] As specific examples of "substituted or unsubstituted alkyl" described in this specification (specific example group G3), the following unsubstituted alkyl (specific example group G3A) and substituted alkyl (specific example group G3B) can be cited. (Here, unsubstituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "substituted alkyl".) Hereinafter, when referred to as "alkyl", both "unsubstituted alkyl" and "substituted alkyl" are included.
[0757] "Substituted alkyl" refers to a group in which one or more hydrogen atoms of an "unsubstituted alkyl" have been substituted with a substituent. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms of an "unsubstituted alkyl" (specific example group G3A) have been substituted with a substituent, and examples of substituted alkyl (specific example group G3B). In this specification, "unsubstituted alkyl" refers to a chain-like alkyl group. Therefore, "unsubstituted alkyl" includes both straight-chain and branched-chain unsubstituted alkyl groups. It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples; the "substituted alkyl" described in this specification also includes groups in which the hydrogen atoms of the alkyl group in specific example group G3B have been further substituted with a substituent, and groups in which the hydrogen atoms of the substituents in specific example group G3B have been further substituted with a substituent.
[0758] • Unsubstituted alkyl groups (specific example group G3A):
[0759] methyl,
[0760] Ethyl,
[0761] n-propyl,
[0762] Isopropyl,
[0763] n-Butyl,
[0764] Isobutyl,
[0765] Sec-butyl and tert-butyl.
[0766] • Substituted alkyl groups (specific example group G3B): heptafluoropropyl (including isomers),
[0767] Pentafluoroethyl,
[0768] 2,2,2-Trifluoroethyl and
[0769] Trifluoromethyl
[0770] • "Substituted or unsubstituted alkenyl groups"
[0771] Specific examples of "substituted or unsubstituted alkenyl groups" (specific example group G4) described in this specification include unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc. (Here, "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "unsubstituted alkenyl group", and "substituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "substituted alkenyl group".) In this specification, when simply referred to as "alkenyl group", both "unsubstituted alkenyl group" and "substituted alkenyl group" are included.
[0772] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" group have been substituted with a substituent. Specific examples of "substituted alkenyl" include the "unsubstituted alkenyl" group (specific example group G4A) having a substituent and examples of substituted alkenyl groups (specific example group G4B). It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples; the "substituted alkenyl" described in this specification also includes groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the alkenyl itself have been further substituted with a substituent, and groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the substituent have been further substituted with a substituent.
[0773] • Unsubstituted alkenyl groups (specific example group G4A):
[0774] vinyl,
[0775] Allyl
[0776] 1-Butenyl,
[0777] 2-Butenyl and
[0778] 3-Butenyl.
[0779] • Substituted alkenyl groups (specific example group G4B):
[0780] 1,3-Butadienyl,
[0781] 1-Methylvinyl
[0782] 1-Methylallyl,
[0783] 1,1-Dimethylallyl,
[0784] 2-Methylallyl and
[0785] 1,2-Dimethylallyl.
[0786] • "Substituted or unsubstituted alkynyl groups"
[0787] As specific examples of "substituted or unsubstituted alkynyl groups" described in this specification (specific example group G5), the following unsubstituted alkynyl groups (specific example group G5A) can be cited. (Here, unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group".) The following description of "alkynyl group" includes both "unsubstituted alkynyl group" and "substituted alkynyl group".
[0788] "Substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" have been replaced by a substituent. Specific examples of "substituted alkynyl group" include groups in which one or more hydrogen atoms in an "unsubstituted alkynyl group" (specific example group G5A) have been replaced by a substituent.
[0789] • Unsubstituted alkynyl group (specific example group G5A): ethynyl group
[0790] • "Substituted or unsubstituted cycloalkyl groups"
[0791] Specific examples of "substituted or unsubstituted cycloalkyl" described in this specification (specific example group G6) include unsubstituted cycloalkyl (specific example group G6A) and substituted cycloalkyl (specific example group G6B), etc. (Here, unsubstituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and substituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl".) In this specification, when referred to only as "cycloalkyl", both "unsubstituted cycloalkyl" and "substituted cycloalkyl" are included.
[0792] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group have been substituted with a substituent. Specific examples of "substituted cycloalkyl" include the group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group (specific example group G6A) have been substituted with a substituent, and examples of substituted cycloalkyl groups (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples. The "substituted cycloalkyl" described in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl" group of specific example group G6B have been substituted with a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted cycloalkyl" group of specific example group G6B have been further substituted with a substituent.
[0793] • Unsubstituted cycloalkyl groups (specific example group G6A):
[0794] Cyclopropyl,
[0795] Cyclobutyl,
[0796] Cyclopentyl,
[0797] Cyclohexyl,
[0798] 1-Adamantyl,
[0799] 2-Adamantyl,
[0800] 1-norborneol and
[0801] 2-norborneol.
[0802] • Substituted cycloalkyl groups (specific example group G6B):
[0803] 4-Methylcyclohexyl.
[0804] ·"-Si(R 901 (R) 902 (R) 903 The group shown in the figure”
[0805] As described in this specification, -Si(R) 901 (R) 902 (R) 903 Specific examples of the group shown in the figure (specific example group G7) can be given as follows:
[0806] -Si(G1)(G1)(G1),
[0807] -Si(G1)(G2)(G2)
[0808] -Si(G1)(G1)(G2),
[0809] -Si(G2)(G2)(G2),
[0810] -Si(G3)(G3)(G3) and
[0811] -Si(G6)(G6)(G6). Here.
[0812] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.
[0813] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.
[0814] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.
[0815] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.
[0816] In -Si(G1)(G1)(G1), multiple G1s may be identical or different from each other.
[0817] In -Si(G1)(G2)(G2), multiple G2s may be the same or different from each other.
[0818] In -Si(G1)(G1)(G2), multiple G1s may be the same or different from each other.
[0819] In -Si(G2)(G2)(G2), multiple G2s may be the same or different from each other.
[0820] In -Si(G3)(G3)(G3), multiple G3s may be identical or different from each other.
[0821] In -Si(G6)(G6)(G6), multiple G6s may be identical or different from each other.
[0822] ·“-O-(R 904 The group shown in the figure”
[0823] As described in this specification, -O-(R) 904 Specific examples of the group shown in the figure (specific example group G8) can be given as follows:
[0824] -O(G1)
[0825] -O(G2),
[0826] -O(G3) and
[0827] -O(G6).
[0828] Here,
[0829] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.
[0830] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.
[0831] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.
[0832] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.
[0833] ·“-S-(R 905 The group shown in the figure”
[0834] As described in this specification, -S-(R) 905 Specific examples of the group shown in the figure (specific example group G9) can be given as follows:
[0835] -S(G1)
[0836] -S(G2),
[0837] -S(G3) and
[0838] -S(G6).
[0839] Here,
[0840] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.
[0841] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.
[0842] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.
[0843] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.
[0844] ·"-N(R 906 (R) 907 The group shown in the figure”
[0845] As described in this specification, -N(R) 906 (R) 907 Specific examples of the group shown (specific example group G10) can be given as follows:
[0846] -N(G1)(G1),
[0847] -N(G2)(G2),
[0848] -N(G1)(G2),
[0849] -N(G3)(G3) and
[0850] -N(G6)(G6).
[0851] Here,
[0852] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.
[0853] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.
[0854] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.
[0855] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.
[0856] In -N(G1)(G1), multiple G1s may be the same or different from each other.
[0857] In -N(G2)(G2), multiple G2s may be the same or different from each other.
[0858] In -N(G3)(G3), multiple G3s may be the same or different from each other.
[0859] In -N(G6)(G6), multiple G6s may be the same or different from each other.
[0860] • "Halogen atom"
[0861] Specific examples of "halogen atoms" described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.
[0862] • "Substituted or unsubstituted fluoroalkyl groups"
[0863] The term "substituted or unsubstituted fluoroalkyl" as used in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom constituting the alkyl group has been replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group have been replaced by fluorine atoms (perfluorinated groups). Unless otherwise specified in this specification, the number of carbon atoms in an "unsubstituted fluoroalkyl" group is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted fluoroalkyl" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl" group have been replaced by a substituent. It should be noted that the term "substituted fluoroalkyl" as used in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in a "substituted fluoroalkyl" group have been further replaced by a substituent, and groups in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl" group have been further replaced by a substituent. As a specific example of "unsubstituted fluoroalkyl", examples can be given of groups in which one or more hydrogen atoms in the above-mentioned "alkyl" (specific example group G3) have been replaced by fluorine atoms.
[0864] • "Substituted or unsubstituted haloalkyl groups"
[0865] The term "substituted or unsubstituted haloalkyl" as used in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom constituting the alkyl group has been replaced by a halogen atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group have been replaced by halogen atoms. Unless otherwise specified in this specification, the number of carbon atoms in an "unsubstituted haloalkyl" group is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted haloalkyl" refers to a group in which one or more hydrogen atoms of a "haloalkyl" group have been replaced by a substituent. It should be noted that "substituted haloalkyl" as used in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in a "substituted haloalkyl" group have been further replaced by a substituent, and groups in which one or more hydrogen atoms of a substituent in a "substituted haloalkyl" group have been further replaced by a substituent. As a specific example of "unsubstituted haloalkyl", examples can be given of groups in which one or more hydrogen atoms of the above-mentioned "alkyl" (specific example group G3) have been substituted with halogen atoms. Haloalkyl is sometimes called haloalkyl.
[0866] • "Substituted or unsubstituted alkoxy groups"
[0867] As a specific example of "substituted or unsubstituted alkoxy group" as described in this specification, it is the group indicated by -O (G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
[0868] • "Substituted or unsubstituted alkylthio groups"
[0869] As a specific example of "substituted or unsubstituted alkylthio group" as described in this specification, it is the group indicated by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
[0870] • "Substituted or unsubstituted aryloxy groups"
[0871] As a specific example of "substituted or unsubstituted aryloxy group" as described in this specification, it is the group indicated by -O (G1), where G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of carbon atoms in the ring of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
[0872] • "Substituted or unsubstituted arylthio groups"
[0873] As a specific example of "substituted or unsubstituted arylthio group" as described in this specification, it is the group indicated by -S(G1), where G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of carbon atoms in the ring of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
[0874] • "Substituted or unsubstituted trialkylsilyl groups"
[0875] As a specific example of "trialkylsilyl" as described in this specification, it is the group represented by -Si(G3)(G3)(G3), where G3 refers to the "substituted or unsubstituted alkyl" described in the specific example group G3. The plurality of G3s in -Si(G3)(G3)(G3) may be identical or different from each other. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the "trialkylsilyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.
[0876] • "Substituted or unsubstituted aralkyl groups"
[0877] As a specific example of "substituted or unsubstituted aralkyl" as described in this specification, it is the group shown as -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl" described in specific example group G3, and G1 is the "substituted or unsubstituted aryl" described in specific example group G1. Therefore, "aralkyl" is a group in which the hydrogen atom of "alkyl" is replaced by "aryl" as a substituent, and is one embodiment of "substituted alkyl". "Unsubstituted aralkyl" is an "unsubstituted alkyl" that is substituted with "unsubstituted aryl", and the number of carbon atoms of "unsubstituted aralkyl" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.
[0878] Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl.
[0879] Unless otherwise specified in this specification, the substituted or unsubstituted aryl groups described herein are preferably phenyl, p-phenyl, meta-phenyl, o-phenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthraceneyl, phenanthryl, pyreneyl, etc. It includes methyl, triphenyl, fluorenyl, 9,9'-spirobisfluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl, etc.
[0880] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic groups described herein are preferably pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, phenanthrolinel, carbazole (1-carbazole, 2-carbazole, 3-carbazole, 4-carbazole or 9-carbazole), benzocarbazole, azacarbazole, diazacarbazole, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophene, and naphtho-benzofuranyl. Benzothiophene, azadibenzothiophene, diazadibenzothiophene, (9-phenyl)carbazoyl ((9-phenyl)carbazo-1-yl, (9-phenyl)carbazo-2-yl, (9-phenyl)carbazo-3-yl or (9-phenyl)carbazo-4-yl), (9-biphenyl)carbazoyl, (9-phenyl)phenylcarbazoyl, diphenylcarbazo-9-yl, phenylcarbazo-9-yl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenyldibenzofuranyl and phenyldibenzothiophene, etc.
[0881] In this specification, the carbazoyl group, unless otherwise specified herein, specifically refers to any one of the following groups.
[0882] [Chemical Formula 18]
[0883]
[0884] In this specification, (9-phenyl)carbazolyl refers specifically to any one of the following groups unless otherwise specified herein.
[0885] [Chemical Formula 19]
[0886]
[0887] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.
[0888] In this specification, dibenzofuranyl and dibenzothiopheneyl are specifically any one of the following groups unless otherwise stated in this specification.
[0889]
Chemical Formula 20
[0890]
[0891] In the above general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.
[0892] Unless otherwise specified in this specification, the substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and tert-butyl.
[0893] • "Substituted or unsubstituted aryl groups"
[0894] Unless otherwise stated, the "substituted or unsubstituted aryl group" described in this specification refers to a divalent group derived from the "substituted or unsubstituted aryl group" by removing one hydrogen atom from the aryl ring. Specific examples of "substituted or unsubstituted aryl group" (specific example group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in specific example group G1 by removing one hydrogen atom from the aryl ring.
[0895] • "Substituted or unsubstituted divalent heterocyclic groups"
[0896] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification refers to a divalent group derived from the aforementioned "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom from the heterocycle. Specific examples of "substituted or unsubstituted divalent heterocyclic groups" (specific example group G13) include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in specific example group G2 by removing one hydrogen atom from the heterocycle.
[0897] • "Substituted or unsubstituted alkylene compounds"
[0898] Unless otherwise stated, "substituted or unsubstituted alkylene" as described in this specification refers to a divalent group derived from the aforementioned "substituted or unsubstituted alkyl" by removing one hydrogen atom from the alkyl chain. Specific examples of "substituted or unsubstituted alkylene" (Specific Example Group G14) include divalent groups derived from the "substituted or unsubstituted alkyl" described in Specific Example Group G3 by removing one hydrogen atom from the alkyl chain.
[0899] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described herein is preferably any one of the groups in the following general formulas (TEMP-42) to (TEMP-68).
[0900]
Chemical Formula 21
[0901]
[0902]
Chemical Formula 22
[0903]
[0904] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.
[0905] In the above general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.
[0906]
Chemical Formula 23
[0907]
[0908] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.
[0909] Formulas Q9 and Q 10 They can form rings by bonding with each other via single bonds.
[0910] In the above general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.
[0911] [Chemical Formula 24]
[0912]
[0913] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.
[0914] In the above general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.
[0915] Unless otherwise specified in this specification, the substituted or unsubstituted divalent heterocyclic group described herein is preferably any group of the following general formulas (TEMP-69) to (TEMP-102).
[0916] [Chemical Formula 25]
[0917]
[0918]
Chemical Formula 26
[0919]
[0920] [Chemical Formula 27]
[0921]
[0922] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.
[0923] [Chemical Formula 28]
[0924]
[0925] [Chemical Formula 29]
[0926]
[0927]
Chemical Formula 30
[0928]
[0929]
Chemical Formula 31
[0930]
[0931] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.
[0932] The above is an explanation of "substituents described in this specification".
[0933] • "Cases where bonds form rings"
[0934] In this specification, the description of "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring, or bonded together to form a substituted or unsubstituted fused ring, or not bonded together" refers to the cases of "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring", "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted fused ring", and "one or more groups of two or more adjacent elements not bonded together".
[0935] The following description addresses the cases where "one or more groups of two or more adjacent rings are bonded together to form a substituted or unsubstituted monocyclic ring" and "one or more groups of two or more adjacent rings are bonded together to form a substituted or unsubstituted fused ring" (hereinafter, these cases are sometimes collectively referred to as "the case of forming a ring by bonding"). The case of anthracene compounds with the following general formula (TEMP-103) whose parent skeleton is anthracene ring will be used as an example.
[0936]
Chemical Formula 32
[0937]
[0938] For example, in R 921 ~R 930 In the case of "one or more groups of two or more adjacent elements bonded together to form a loop", the group consisting of two adjacent elements as a group refers to R. 921 With R 922 group, R 922 With R 923 group, R 923 With R 924 group, R 924 With R 930 group, R 930 With R 925 group, R 925 With R 926 group, R 926 With R 927 group, R 927 With R 928 group, R 928 With R 929 The group, and R 929 With R 921 The group.
[0939] The phrase "one or more groups" refers to the fact that two or more of the aforementioned adjacent groups can simultaneously form a loop. For example, in R... 921 With R 922 They bond together to form a ring Q A Moreover, R 925 With R 926 They bond together to form a ring Q B In this case, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).
[0940]
Chemical Formula 33
[0941]
[0942] The formation of rings from "groups of two or more adjacent elements" includes not only the case of bonds formed by groups of "two" adjacent elements, as in the previous example, but also the case of bonds formed by groups of "three or more" adjacent elements. For example, it refers to R... 921 With R 922 They bond together to form a ring Q A And R 922 With R 923 They bond together to form a ring Q C , consisting of 3 adjacent (R) 921 R 922 and R 923When the groups of components Q bond together to form a ring and fuse to the anthracene matrix, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q... A and ring Q C There are a total of R 922 .
[0943]
Chemical Formula 34
[0944]
[0945] In the formed "single ring" or "fused ring," the structure of the ring alone can be either a saturated ring or an unsaturated ring. Even when "one of the groups of two adjacent rings" forms a "single ring" or "fused ring," that "single ring" or "fused ring" can form either a saturated ring or an unsaturated ring. For example, the ring Q formed in the above general formula (TEMP-104) A and ring Q B Each is either a "single ring" or a "fused ring". Additionally, the ring Q formed in the above general formula (TEMP-105) A and Q ring C It is a "fused ring". The ring Q of the above general formula (TEMP-105) A With ring Q C Through ring Q A With ring Q C Fusing together forms a fused ring. The ring Q of the above general formula (TMEP-104) A If it is a benzene ring, then ring Q A It is a single ring. The ring Q in the above general formula (TMEP-104) A If it is a naphthalene ring, then ring Q A It is a fused ring.
[0946] "Unsaturated rings" refer to aromatic hydrocarbon rings or aromatic heterocycles. "Saturated rings" refer to aliphatic hydrocarbon rings or non-aromatic heterocycles.
[0947] As a specific example of an aromatic hydrocarbon ring, the structure formed by the hydrogen atom-terminated group in specific example group G1 can be cited.
[0948] As a specific example of an aromatic heterocycle, one can cite the structure formed by end-capping an aromatic heterocycle group with hydrogen atoms in specific example group G2.
[0949] As a specific example of an aliphatic hydrocarbon ring, the structure formed by the hydrogen atom-terminated group in specific example group G6 can be cited.
[0950] "Ring formation" refers to the formation of a ring solely by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton forming a ring with one or more other optional elements. For example, R shown in the above general formula (TEMP-104) 921 With R 922 The ring Q formed by mutual bonding A It refers to R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 The carbon atoms of the bonded anthracene framework form rings with one or more optional elements. As a specific example, in the case of R... 921 With R 922 Forming ring Q A In the case of R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 When the bonded anthracene skeleton carbon atoms and 4 carbon atoms form a monocyclic unsaturated ring, R 921 With R 922 The resulting ring is a benzene ring.
[0951] Here, "optional element" is preferably selected from at least one element chosen from the group consisting of carbon, nitrogen, oxygen, and sulfur, unless otherwise specified in this specification. In the case of optional elements (e.g., carbon or nitrogen), non-ring bonds can be capped by hydrogen atoms or replaced by "optional substituents" described later. When optional elements other than carbon are included, the resulting ring is a heterocycle.
[0952] Unless otherwise specified in this specification, the "one or more optional elements" constituting a monocyclic or fused ring are preferably two or more and 15 or less, more preferably three or more and 12 or less, and even more preferably three or more and 5 or less.
[0953] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".
[0954] Unless otherwise stated in this specification, "unsaturated ring" is preferred over "saturated ring".
[0955] Unless otherwise stated in this specification, "monocyclic" is preferably a benzene ring.
[0956] Unless otherwise stated in this specification, the "unsaturated ring" is preferably a benzene ring.
[0957] In the case of "one or more groups of two or more adjacent atoms forming a substituted or unsubstituted monocyclic ring" or "a substituted or unsubstituted fused ring formed by mutual bonding", unless otherwise stated in this specification, it is preferred that one or more groups of two or more adjacent atoms form an unsaturated ring formed by mutual bonding of a plurality of atoms of a parent skeleton and at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur.
[0958] When the aforementioned "monocyclic" or "fused-ring" rings have substituents, the substituents are, for example, the "optional substituents" described later. Specific examples of substituents when the aforementioned "monocyclic" or "fused-ring" rings have substituents are the substituents described in the section "Substituents Represented in This Specification" above.
[0959] When the aforementioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of substituents when the aforementioned "monocyclic" or "fused ring" has a substituent are the substituents described in the section "Substituents Represented in This Specification" above.
[0960] The above explains the cases of "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring" and "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted fused ring" ("the case of bonding to form a ring").
[0961] Substituents when described as "substituted or unsubstituted"
[0962] In one embodiment of this specification, the substituents described above as "substituted or unsubstituted" (sometimes referred to as "optional substituents" in this specification) are, for example, selected from...
[0963] Unsubstituted alkyl groups having 1 to 50 carbon atoms
[0964] Unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0965] Unsubstituted acetylinyl groups with 2 to 50 carbon atoms
[0966] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0967] -Si(R 901 (R) 902 (R) 903 ),
[0968] -O-(R 904 ),
[0969] -S-(R905 ),
[0970] -N(R 906 (R) 907 ),
[0971] Halogen atom, cyano group, nitro group,
[0972] Unsubstituted aryl groups with 6 to 50 carbon atoms and
[0973] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms
[0974] Groups, etc., in the composition group
[0975] Here, R 901 ~R 907 Each independently
[0976] hydrogen atom,
[0977] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0978] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0979] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0980] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[0981] R 901 When there are more than two, more than two R 901 They are the same or different.
[0982] R 902 When there are more than two, more than two R 902 They are the same or different.
[0983] R 903 When there are more than two, more than two R 903 They are the same or different.
[0984] R 904 When there are more than two, more than two R 904 They are the same or different.
[0985] R 905 When there are more than two, more than two R 905 They are the same or different.
[0986] R 906 When there are more than two, more than two R 906 They are the same or different.
[0987] R907 When there are more than two, more than two R 907 They are the same or different.
[0988] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.
[0989] Alkyl groups with 1 to 50 carbon atoms
[0990] Aryl groups with 6 to 50 carbon atoms and
[0991] Heterocyclic groups with 5 to 50 cyclic atoms
[0992] The groups in the group.
[0993] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.
[0994] Alkyl groups having 1 to 18 carbon atoms
[0995] aryl groups with 6 to 18 carbon atoms and
[0996] Heterocyclic groups with 5 to 18 cyclic atoms
[0997] The groups in the group.
[0998] Specific examples of each of the optional substituents are those described in the section "Substituents as described in this specification" above.
[0999] Unless otherwise stated in this specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring" with each other, preferably forming a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably forming a benzene ring.
[1000] Unless otherwise stated in this specification, optional substituents may also have other substituents. Any further substituents that may be present as optional substituents are the same as those described above.
[1001] In this specification, the numerical range referred to as "AA~BB" refers to the range included by taking the value AA recorded before "AA~BB" as the lower limit and the value BB recorded after "AA~BB" as the upper limit.
[1002] [First Implementation]
[1003] (Organic electroluminescent device)
[1004] The organic electroluminescent element according to this embodiment includes 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. The first light-emitting layer contains a first compound having at least one group represented by the following general formula (11) 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. In the organic EL element according to this embodiment, the first light-emitting layer and the second light-emitting layer are directly connected.
[1005] The organic electroluminescent element involved in this embodiment has, in sequence, an anode, a first light-emitting layer, a second light-emitting layer, and a cathode.
[1006] In this specification, the layer structure in which "the first light-emitting layer and the second light-emitting layer are directly connected" may also include any of the following schemes (LS1), (LS2) and (LS3).
[1007] (LS1) A scheme in which a region is formed where the first compound and the second compound coexist during the vapor deposition process of the compound involved in the first light-emitting layer and the vapor deposition process of the compound involved in the second light-emitting layer, and the region exists at the interface between the first light-emitting layer and the second light-emitting layer.
[1008] (LS2) In the case where the first light-emitting layer and the second light-emitting layer contain luminescent compounds, a region in which the first compound, the second compound and the luminescent compound coexist is generated during the vapor deposition process of the compound involved in the first light-emitting layer and the vapor deposition process of the compound involved in the second light-emitting layer, and the region exists at the interface between the first light-emitting layer and the second light-emitting layer.
[1009] (LS3) In the case where the first light-emitting layer and the second light-emitting layer contain a luminescent compound, a region formed by the luminescent compound, a region formed by the first compound, or a region formed by the second compound is generated during the vapor deposition process of the compound involved in the first light-emitting layer and the vapor deposition process of the compound involved in the second light-emitting layer, and the region exists at the interface between the first light-emitting layer and the second light-emitting layer.
[1010] In this specification, "main material" refers, for example, to a material having a content of "50% by mass or more of the layer". Therefore, for example, the content of the first compound shown in the following general formula (1) in the first light-emitting layer is 50% by mass or more of the total mass of the first light-emitting layer. The content of the second compound shown in the following general formula (2) in the second light-emitting layer is, for example, 50% by mass or more of the total mass of the second light-emitting layer.
[1011] (Emitting wavelength of organic EL devices)
[1012] The organic electroluminescent element involved in this embodiment preferably emits light with a main peak wavelength of 430 nm or more and 480 nm or less when the element is driven.
[1013] The peak wavelength of the light emitted by the organic EL device during device driving was determined as follows. A CS-2000 spectrophotometer (manufactured by Konica Minolta) was used to measure the wavelength of the light emitted by the organic EL device while applying a voltage to achieve a current density of 10 mA / cm². 2 The spectrophotometer of emission intensity at that time was obtained. In the obtained spectrophotometer of emission intensity, the peak wavelength of the emission spectrum at which the emission intensity reaches the maximum was measured and taken as the main peak wavelength (unit: nm).
[1014] The organic EL element according to this embodiment may have one or more organic layers in addition to the first and second light-emitting layers. Examples of organic layers include at least one layer selected from hole injection layer, hole transport layer, light-emitting layer, electron injection layer, electron transport layer, hole blocking layer, and electron blocking layer.
[1015] In the organic EL element of this embodiment, the organic layer may consist only of a first light-emitting layer and a second light-emitting layer, or it may also have at least one layer selected from, for example, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole blocking layer, and an electron blocking layer.
[1016] (Hole transport layer)
[1017] In the organic EL element of this embodiment, it is preferable to have a hole transport layer between the anode and the first light-emitting layer.
[1018] In the organic EL element of this embodiment, it is preferable to have an electron transport layer between the cathode and the second light-emitting layer.
[1019] Figure 1 The general configuration of an example of an organic EL element involved in this embodiment is shown.
[1020] The organic EL element 1 includes a light-transmitting 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 formed by stacking a hole injection layer 6, a hole transport layer 7, a first light-emitting layer 51, a second light-emitting layer 52, an electron transport layer 8, and an electron injection layer 9 in that order, starting from the anode 3 side.
[1021] (First compound)
[1022] In the organic EL element involved in this embodiment, the first compound is a compound represented by the following general formula (1).
[1023]
Chemical Formula 35
[1024]
[1025] (In the above general formula (1),
[1026] R 101 ~R 110 Each independently
[1027] hydrogen atom,
[1028] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1029] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1030] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1031] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1032] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1033] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1034] -O-(R 904 The groups shown in the figure,
[1035] -S-(R 905 The groups shown in the figure,
[1036] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1037] -C(=O)R 801 The groups shown
[1038] -COOR 802 The groups shown
[1039] Halogen atoms,
[1040] cyano,
[1041] Nitro,
[1042] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1043] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[1044] The groups represented by the above general formula (11),
[1045] Among them, R 101 ~R 110At least one of them is a group represented by the general formula (11) above.
[1046] When there are multiple groups represented by the above general formula (11), the multiple groups represented by the above general formula (11) may be the same as or different from each other.
[1047] L 101 for
[1048] single bond,
[1049] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1050] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1051] Ar 101 for
[1052] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1053] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1054] mx is 0, 1, 2, 3, 4, or 5.
[1055] In L 101 When there are more than two, more than two L 101 They are the same or different.
[1056] In Ar 101 In the case of two or more Ar, two or more Ar 101 They are the same or different.
[1057] In the above general formula (11), * indicates the bonding position with the pyrene ring in the above general formula (1).
[1058] (In the first compound involved in this embodiment, R) 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently
[1059] hydrogen atom,
[1060] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1061] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1062] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1063] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1064] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[1065] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[1066] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.
[1067] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
[1068] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.
[1069] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.
[1070] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.
[1071] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[1072] In R 802 In the case of multiple Rs, multiple Rs 802 (They may be the same or different.)
[1073] In the organic EL element involved in this embodiment, it is also preferable to use the above general formula (1).
[1074] R 101 ~R 110 Each independently
[1075] hydrogen atom,
[1076] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1077] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1078] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1079] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1080] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1081] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1082] -O-(R 904 The groups shown in the figure,
[1083] -S-(R 905 The groups shown in the figure,
[1084] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1085] -C(=O)R 801 The groups shown
[1086] -COOR 802 The groups shown
[1087] Halogen atoms,
[1088] cyano,
[1089] Nitro,
[1090] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1091] The groups represented by the above general formula (11),
[1092] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11) above.
[1093] When there are multiple groups represented by the above general formula (11), the multiple groups represented by the above general formula (11) may be the same as or different from each other.
[1094] L 101 for
[1095] single key or
[1096] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms in a cyclic structure.
[1097] Ar 101 For substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic structure,
[1098] mx is 0, 1, 2, 3, 4, or 5.
[1099] Ar 101 It is neither a substituted nor an unsubstituted pyrene group.
[1100] L 101 It is neither a replaced nor unreplaced pyrene group.
[1101] R, which is not a group represented by the above general formula (11) 101 ~R 110 The substituted or unsubstituted aryl group with 6 to 50 carbon atoms is not a substituted or unsubstituted pyrene group.
[1102] In L 101 When there are more than two, more than two L 101 They are the same or different.
[1103] In Ar 101 In the case of two or more Ar, two or more Ar 101 They are the same or different.
[1104] In the organic EL element of this embodiment, the group represented by the above general formula (11) is preferably the group represented by the following general formula (111).
[1105]
Chemical Formula 36
[1106]
[1107] (In the above general formula (111),
[1108] X1 is CR 123 R 124 oxygen atom, sulfur atom or NR 125 ,
[1109] L 111 and L 112 Each independently
[1110] single bond,
[1111] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1112] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1113] ma can be 0, 1, 2, 3, or 4.
[1114] mb can be 0, 1, 2, 3, or 4.
[1115] ma+mb is 0, 1, 2, 3 or 4.
[1116] Ar 101 Ar in the above general formula (11)101 Same meaning
[1117] R 121 R 122 R 123 R 124 and R 125 Each independently
[1118] hydrogen atom,
[1119] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1120] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1121] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1122] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1123] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1124] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1125] -O-(R 904 The groups shown in the figure,
[1126] -S-(R 905 The groups shown in the figure,
[1127] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1128] -C(=O)R 801 The groups shown
[1129] -COOR 802 The groups shown
[1130] Halogen atoms,
[1131] cyano,
[1132] Nitro,
[1133] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1134] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1135] mc is 3.
[1136] 3 Rs 121 They are the same or different.
[1137] md is 3
[1138] 3 Rs 122 (They may be the same or different.)
[1139] In the organic EL element involved in this embodiment, it is preferable to use the above general formula (111).
[1140] X1 is CR 123 R 124 ,
[1141] L 111 and L 112 Each independently
[1142] single key or
[1143] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms in a cyclic structure.
[1144] ma can be 0, 1, 2, 3, or 4.
[1145] mb can be 0, 1, 2, 3, or 4.
[1146] ma+mb is 0, 1, 2, 3 or 4.
[1147] Ar 101 Ar in the above general formula (11) 101 Same meaning
[1148] R 121 R 122 R 123 and R 124 Each independently
[1149] hydrogen atom,
[1150] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1151] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1152] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1153] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1154] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1155] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1156] -O-(R 904 The groups shown in the figure,
[1157] -S-(R905 The groups shown in the figure,
[1158] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1159] -C(=O)R 801 The groups shown
[1160] -COOR 802 The groups shown
[1161] Halogen atoms,
[1162] cyano,
[1163] Nitro, or
[1164] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[1165] mc is 3.
[1166] 3 Rs 121 They are the same or different.
[1167] md is 3
[1168] 3 Rs 122 They are the same or different.
[1169] In the group represented by the above general formula (111), at positions *1 to *8 of the carbon atoms in the ring structure represented by the following general formula (111a), L 111 Bonded to any position from *1 to *4, R 121 Bonded to the remaining 3 positions in *1 to *4, L 112 Bonded to any position from *5 to *8, R 122 It is bonded to the other 3 positions in *5 to *8.
[1170]
Chemical Formula 37
[1171]
[1172] For example, in the groups shown in the above general formula (111), in L 111 The position of the carbon atom *2 bonded to the ring structure shown in the above general formula (111a), L 112 When the carbon atom of *7 in the ring structure shown in the above general formula (111a) is bonded, the group shown in the above general formula (111) is represented by the following general formula (111b).
[1173] [Chemical Formula 38]
[1174]
[1175] (In the above general formula (111b),
[1176] X1, L 111 L 112 ma, mb, Ar 101 R 121 R 122 R 123 R 124 and R 125 Each independently relates to X1 and L in the above general formula (111). 111 L 112 ma, mb, Ar 101 R 121 R 122 R 123 R 124 and R 125 Same meaning
[1177] Multiple R 121 They are the same or different.
[1178] Multiple R 122 (They may be the same or different.)
[1179] In the organic EL element of this embodiment, the group represented by the above general formula (111) is preferably the group represented by the above general formula (111b).
[1180] In the organic EL element involved in this embodiment, it is preferred that,
[1181] ma is 0, 1, or 2.
[1182] mb can be 0, 1, or 2.
[1183] In the organic EL element involved in this embodiment, it is preferred that,
[1184] ma is 0 or 1.
[1185] mb is 0 or 1.
[1186] In the organic EL element involved in this embodiment, Ar 101 Preferably, it is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.
[1187] In the organic EL element involved in this embodiment,
[1188] Ar 101 Preferred
[1189] Substituted or unsubstituted phenyl
[1190] Substituted or unsubstituted naphthyl groups
[1191] Substituted or unsubstituted biphenyl,
[1192] Substituted or unsubstituted triphenyl,
[1193] Substituted or unsubstituted pyrene,
[1194] Replaced or unreplaced foie gras, or
[1195] Substituted or unsubstituted fluorene group.
[1196] In the organic EL element involved in this embodiment,
[1197] Ar 101 It is also preferred to use the groups shown in general formula (12), general formula (13) or general formula (14) below.
[1198] [Chemical Formula 39]
[1199]
[1200] (In the above general formulas (12), (13) and (14),
[1201] R 111 ~R 120 Each independently
[1202] hydrogen atom,
[1203] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1204] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1205] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1206] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1207] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1208] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1209] -O-(R 904 The groups shown in the figure,
[1210] -S-(R 905 The groups shown in the figure,
[1211] -N(R 906 (R) 907 The groups shown in the figure,
[1212] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1213] -C(=O)R 124 The groups shown
[1214] -COOR 125 The groups shown
[1215] Halogen atoms,
[1216] cyano,
[1217] Nitro,
[1218] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1219] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1220] In the above general formulas (12), (13), and (14), * indicates the same as L in the above general formula (11). 101 The bonding position, or the L in the above general formula (111) or general formula (111b) 112 (The bonding location.)
[1221] In the organic EL element involved in this embodiment,
[1222] The first compound is preferably represented by the following general formula (101).
[1223]
Chemical Formula 40
[1224]
[1225] (In the above general formula (101),
[1226] R 101 ~R 120 Each independently
[1227] hydrogen atom,
[1228] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1229] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1230] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1231] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1232] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1233] -Si(R 901 (R) 902(R) 903 The groups shown in the figure,
[1234] -O-(R 904 The groups shown in the figure,
[1235] -S-(R 905 The groups shown in the figure,
[1236] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1237] -C(=O)R 801 The groups shown
[1238] -COOR 802 The groups shown
[1239] Halogen atoms,
[1240] cyano,
[1241] Nitro,
[1242] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1243] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1244] Among them, R 101 ~R 110 One of them represents L 101 The bonding position, R 111 ~R 120 One of them represents L 101 The bonding position,
[1245] L 101 for
[1246] single bond,
[1247] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1248] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1249] mx is 0, 1, 2, 3, 4, or 5.
[1250] In L 101 When there are more than two, more than two L 101 (They may be the same or different.)
[1251] In the organic EL element involved in this embodiment,
[1252] L 101 Preferred
[1253] single key, or
[1254] A substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure.
[1255] In the organic EL element involved in this embodiment,
[1256] The first compound is preferably represented by the following general formula (102).
[1257]
Chemical Formula 41
[1258]
[1259] (In the above general formula (102),
[1260] R 101 ~R 120 Each independently relates to R in the above general formula (101). 101 ~R 120 Same meaning
[1261] Among them, R 101 ~R 110 One of them represents L 111 The bonding position, R 111 ~R 120 One of them represents L 112 The bonding position,
[1262] X1 is CR 123 R 124 oxygen atom, sulfur atom or NR 125 ,
[1263] L 111 and L 112 Each independently
[1264] single bond,
[1265] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1266] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1267] ma can be 0, 1, 2, 3, or 4.
[1268] mb can be 0, 1, 2, 3, or 4.
[1269] ma+mb is 0, 1, 2, 3 or 4.
[1270] R 121 R 122 R 123 R 124 and R 125 Each independently
[1271] hydrogen atom,
[1272] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1273] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1274] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1275] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1276] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1277] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1278] -O-(R 904 The groups shown in the figure,
[1279] -S-(R 905 The groups shown in the figure,
[1280] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1281] -C(=O)R 801 The groups shown
[1282] -COOR 802 The groups shown
[1283] Halogen atoms,
[1284] cyano,
[1285] Nitro,
[1286] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1287] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1288] mc is 3.
[1289] 3 Rs 121 They are the same or different.
[1290] md is 3
[1291] 3 Rs 122 (They may be the same or different.)
[1292] In the compounds represented by the above general formula (102), it is preferred that,
[1293] ma is 0, 1, or 2.
[1294] mb can be 0, 1, or 2.
[1295] In the compounds represented by the above general formula (102), it is preferred that,
[1296] ma is 0 or 1.
[1297] mb is 0 or 1.
[1298] In the organic EL element involved in this embodiment,
[1299] R 101 ~R 110 Two or more of them are preferably groups represented by the above general formula (11).
[1300] In the organic EL element involved in this embodiment,
[1301] Preferably, R 101 ~R 110 Two or more of them are groups represented by the general formula (11) above and Ar 101 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.
[1302] In the organic EL element involved in this embodiment, it is preferred that,
[1303] Ar 101 It is neither a substituted nor an unsubstituted pyrene group.
[1304] L 101 It is neither a replaced nor unreplaced pyrene group.
[1305] R, which is not a group represented by the above general formula (11) 101 ~R 110 The substituted or unsubstituted aryl group with 6 to 50 carbon atoms is not a substituted or unsubstituted pyrene group.
[1306] In the organic EL element involved in this embodiment, the substituents described as "substituted or unsubstituted" preferably do not include substituted or unsubstituted pyrene groups.
[1307] In Ar 101 When the aryl group with 6 to 50 carbon atoms is substituted, it is also preferred as Ar. 101 The aryl group has substituents that are not heterocyclic groups.
[1308] In the organic EL element involved in this embodiment, it is also preferred that the first compound has at least two groups represented by the above general formula (11).
[1309] When the first compound has at least two groups represented by the above general formula (11), it is also preferable to have the above general formula (1).
[1310] R 101 ~R 110 Each independently
[1311] hydrogen atom,
[1312] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1313] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1314] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1315] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1316] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1317] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1318] -O-(R 904 The groups shown in the figure,
[1319] -S-(R 905 The groups shown in the figure,
[1320] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1321] -C(=O)R 801 The groups shown
[1322] -COOR 802 The groups shown
[1323] Halogen atoms,
[1324] cyano,
[1325] Nitro, or
[1326] The groups represented by the above general formula (11),
[1327] Among them, R 101 ~R 110 Two or more of them are groups represented by the general formula (11) above.
[1328] When there are multiple groups represented by the above general formula (11), the multiple groups represented by the above general formula (11) may be the same as or different from each other.
[1329] L101 It is a single key.
[1330] Ar 101 It is a heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1331] mx is 0
[1332] In Ar 101 In the case of two or more Ar, two or more Ar 101 They are the same or different.
[1333] When mx is 0, Ar 101 It is bonded to the pyrene ring in the above general formula (1) by a single bond.
[1334] In the organic EL element involved in this embodiment, R is also preferred. 101 ~R 110 Two or three of them are groups represented by the general formula (11) above.
[1335] In the organic EL element involved in this embodiment, it is also preferable to use the above general formula (1).
[1336] R 101 ~R 110 Each independently
[1337] hydrogen atom,
[1338] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1339] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1340] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1341] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1342] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1343] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1344] -O-(R 904 The groups shown in the figure,
[1345] -S-(R 905 The groups shown in the figure,
[1346] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1347] -C(=O)R 801The groups shown
[1348] -COOR 802 The groups shown
[1349] Halogen atoms,
[1350] cyano,
[1351] Nitro,
[1352] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1353] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[1354] The groups represented by the above general formula (11),
[1355] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11) above.
[1356] When there are multiple groups represented by the above general formula (11), the multiple groups represented by the above general formula (11) may be the same as or different from each other.
[1357] L 101 It is a divalent heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1358] Ar 101 It is a heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1359] mx is 1, 2, 3, 4 or 5.
[1360] R, which is not a group represented by the above general formula (11) 101 ~R 110 The substituted or unsubstituted aryl group with 6 to 50 carbon atoms is not a substituted or unsubstituted pyrene group.
[1361] In L 101 When there are more than two, more than two L 101 They are the same or different.
[1362] In Ar 101 In the case of two or more Ar, two or more Ar 101 They are the same or different.
[1363] In the organic EL element involved in this embodiment, it is also preferable to use the above general formula (1).
[1364] R 101 ~R 110 Each independently
[1365] hydrogen atom,
[1366] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1367] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1368] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1369] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1370] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1371] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1372] -O-(R 904 The groups shown in the figure,
[1373] -S-(R 905 The groups shown in the figure,
[1374] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1375] -C(=O)R 801 The groups shown
[1376] -COOR 802 The groups shown
[1377] Halogen atoms,
[1378] cyano,
[1379] Nitro,
[1380] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1381] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[1382] The groups represented by the above general formula (11),
[1383] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11) above.
[1384] Among them, R 101 ~R 110 At least one of them is a heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms.
[1385] When there are multiple groups represented by the above general formula (11), the multiple groups represented by the above general formula (11) may be the same as or different from each other.
[1386] L 101 for
[1387] single key or
[1388] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms in a cyclic structure.
[1389] Ar 101 For substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic structure,
[1390] mx is 0, 1, 2, 3, 4, or 5.
[1391] Ar 101 It is neither a substituted nor an unsubstituted pyrene group.
[1392] L 101 It is neither a replaced nor unreplaced pyrene group.
[1393] R, which is not a group represented by the above general formula (11) 101 ~R 110 The substituted or unsubstituted aryl group with 6 to 50 carbon atoms is not a substituted or unsubstituted pyrene group.
[1394] In L 101 When there are more than two, more than two L 101 They are the same or different.
[1395] In Ar 101 In the case of two or more Ar, two or more Ar 101 They are the same or different.
[1396] It is also preferred as R 101 ~R 110 The heterocyclic group with 5 to 50 cyclic atoms, whether substituted or unsubstituted, is selected from the group consisting of a monocyclic heterocyclic group, a heterocyclic group formed by the fusion of two rings, and a heterocyclic group formed by the fusion of three rings.
[1397] In the organic EL element involved in this embodiment, R is also preferred. 101 ~R 110 One or two of them are groups represented by the general formula (11) above.
[1398] In the organic EL element involved in this embodiment, mx is preferably 1, 2, 3, 4 or 5, and L 101 It is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure.
[1399] In the organic EL element involved in this embodiment, it is preferable to use the above general formula (1).
[1400] R 101 ~R 110 Each independently
[1401] hydrogen atom,
[1402] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1403] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1404] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1405] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1406] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1407] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1408] -O-(R 904 The groups shown in the figure,
[1409] -S-(R 905 The groups shown in the figure,
[1410] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1411] -C(=O)R 801 The groups shown
[1412] -COOR 802 The groups shown
[1413] Halogen atoms,
[1414] cyano,
[1415] Nitro,
[1416] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1417] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[1418] The groups represented by the above general formula (11),
[1419] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11) above.
[1420] When there are multiple groups represented by the above general formula (11), the multiple groups represented by the above general formula (11) may be the same as or different from each other.
[1421] L 101 for
[1422] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1423] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1424] Ar 101 It is a heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1425] mx is 1, 2, 3, 4 or 5.
[1426] Ar 101 It is a heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1427] mx is 1, 2, 3, 4 or 5.
[1428] L 101 It is neither a replaced nor unreplaced pyrene group.
[1429] R, which is not a group represented by the above general formula (11) 101 ~R 110 The substituted or unsubstituted aryl group with 6 to 50 carbon atoms is not a substituted or unsubstituted pyrene group.
[1430] In L 101 When there are more than two, more than two L 101 They are the same or different.
[1431] In Ar 101 In the case of two or more Ar, two or more Ar 101 Whether they are the same or different, L is preferred. 101 It is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure.
[1432] In the organic EL element involved in this embodiment, it is also preferable to use the above general formula (1).
[1433] R 101 ~R 110 Each independently
[1434] hydrogen atom,
[1435] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1436] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1437] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1438] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1439] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1440] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1441] -O-(R 904 The groups shown in the figure,
[1442] -S-(R 905 The groups shown in the figure,
[1443] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1444] -C(=O)R 801 The groups shown
[1445] -COOR 802 The groups shown
[1446] Halogen atoms,
[1447] cyano,
[1448] Nitro,
[1449] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1450] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[1451] The groups represented by the above general formula (11),
[1452] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11) above.
[1453] When there are multiple groups represented by the above general formula (11), the multiple groups represented by the above general formula (11) may be the same as or different from each other.
[1454] L 101 It is a divalent heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1455] Ar 101 For substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic structure,
[1456] mx is 1, 2, 3, 4 or 5.
[1457] Ar 101 It is neither a substituted nor an unsubstituted pyrene group.
[1458] R, which is not a group represented by the above general formula (11) 101 ~R 110 The substituted or unsubstituted aryl group with 6 to 50 carbon atoms is not a substituted or unsubstituted pyrene group.
[1459] In L 101 When there are more than two, more than two L 101 They are the same or different.
[1460] In Ar 101 In the case of two or more Ar, two or more Ar 101 They are the same or different.
[1461] In the above general formula (11), * indicates the bonding position with the pyrene ring in the above general formula (1).
[1462] In the organic EL element involved in this embodiment, L is also preferred. 101 It is an arylene group selected from at least one of the following groups: substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorenediyl, and substituted or unsubstituted phenanthylene; or a divalent heterocyclic group selected from at least one of the following groups: substituted or unsubstituted dibenzofurandiyl, substituted or unsubstituted dibenzothiophenediyl, and substituted or unsubstituted carbazolediyl.
[1463] In the organic EL element involved in this embodiment, at least one L is also preferred. 101 It is an aryl group selected from at least one of the following groups: substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorenediyl, and substituted or unsubstituted phenanthylene.
[1464] In the organic EL element involved in this embodiment, at least one L is also preferred. 101 It is a divalent heterocyclic group selected from at least one of the following groups: substituted or unsubstituted dibenzofuran dimethyl, substituted or unsubstituted dibenzothiophene dimethyl, and substituted or unsubstituted carbazole dimethyl.
[1465] In the organic EL element involved in this embodiment, mx is preferably 1, 2, 3, 4 or 5, with at least one L 101It is an aryl group selected from at least one of the following groups: substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorenediyl, and substituted or unsubstituted phenanthylene.
[1466] In the organic EL element involved in this embodiment, mx is preferably 1, 2, 3, 4 or 5, with at least one L 101 It is a divalent heterocyclic group selected from at least one of the following groups: substituted or unsubstituted dibenzofuran dimethyl, substituted or unsubstituted dibenzothiophene dimethyl, and substituted or unsubstituted carbazole dimethyl.
[1467] In the organic EL element involved in this embodiment, Ar is also preferred. 101 It is an aryl group formed by the fusion of four or more rings.
[1468] In the organic EL element involved in this embodiment, Ar is also preferred. 101 It is a heterocyclic group composed of four or more rings fused together.
[1469] In the organic EL element involved in this embodiment, Ar is also preferred. 101 A heterocyclic group composed of fused four or more rings, where mx is 1, 2, 3, 4, or 5, and at least one L... 101 It is an aryl group selected from at least one of the following groups: substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorenediyl, and substituted or unsubstituted phenanthylene.
[1470] In one embodiment, the first compound is a compound having only one pyrene ring in its molecule (sometimes referred to as a monopyrene compound).
[1471] The first compound is a monopyrene compound and Ar 101 When the aryl group is formed by fusion of four or more rings or the heterocyclic group is formed by fusion of four or more rings, mx is preferably 1, 2, 3, 4 or 5, with at least one L. 101 Not a single bond (i.e., L) 101The linking group is preferably an arylene group selected from at least one of the following groups: substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorenediyl, and substituted or unsubstituted phenanthylene; or a divalent heterocyclic group selected from at least one of the following groups: substituted or unsubstituted dibenzofurandiyl, substituted or unsubstituted dibenzothiophenediyl, and substituted or unsubstituted carbazolediyl. By having such a linking group positioned in the monopyrene compound between the pyrene ring and an aryl group formed by the fusion of four or more rings, or a heterocyclic group formed by the fusion of four or more rings, the decrease in hole mobility can be suppressed, and the decrease in the luminous efficiency of the organic EL element can also be suppressed. Furthermore, the linking group preferably does not contain a carbazole ring because electron injection may decrease. In monopyrene compounds, by having a linking group between a pyrene ring and an aryl group formed by fusion of four or more rings or a heterocyclic group formed by fusion of four or more rings, it is possible to suppress the decrease in electron injection into the light-emitting layer containing the monopyrene compound, and also to suppress the decrease in the luminous efficiency of organic EL elements.
[1472] In the organic EL element involved in this embodiment, Ar is also preferred. 101 for
[1473] Substituted or unsubstituted phenyl
[1474] Substituted or unsubstituted naphthyl groups
[1475] Substituted or unsubstituted biphenyl,
[1476] Substituted or unsubstituted triphenyl,
[1477] Replaced or unreplaced foie gras, or
[1478] Substituted or unsubstituted fluorene group.
[1479] In the organic EL element involved in this embodiment, R is also preferred. 101 ~R 110 One of them is the group shown in the above general formula (11).
[1480] In the organic EL element involved in this embodiment, mx is preferably 1.
[1481] In the organic EL element involved in this embodiment,
[1482] Preferably, the R group is not the group represented by the general formula (11) above. 101 ~R 110 Each independently
[1483] hydrogen atom,
[1484] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1485] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1486] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1487] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1488] In the organic EL element involved in this embodiment,
[1489] Preferably, the R group is not the group represented by the general formula (11) above. 101 ~R 110 Each independently
[1490] hydrogen atom,
[1491] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[1492] Cycloalkyl groups, substituted or unsubstituted, having 3 to 50 carbon atoms.
[1493] In the organic EL element involved in this embodiment, the R group is not the group shown in the above general formula (11). 101 ~R 110 Hydrogen atoms are preferred.
[1494] In both the first and second compounds described above, the groups described as "substituted or unsubstituted" are preferably "unsubstituted".
[1495] In the organic EL element involved in this embodiment,
[1496] For example, R in the first compound represented by the above general formula (1) 101 To R 110 Two of them are groups represented by general formula (11).
[1497] In the organic EL element involved in this embodiment,
[1498] For example, R in the first compound represented by the above general formula (1) 101 To R 110 Three of them are groups represented by general formula (11).
[1499] In the organic EL element involved in this embodiment,
[1500] For example, R in the first compound represented by the above general formula (1) 101 To R 110 Four of them are groups represented by general formula (11).
[1501] In the organic EL element involved in this embodiment,
[1502] For example, R in the first compound represented by the above general formula (1) 101 To R 110 One of them is a group represented by general formula (11), and mx is 1 or more.
[1503] In the organic EL element involved in this embodiment,
[1504] For example, R in the first compound represented by the above general formula (1) 101 To R 110 One of them is a group represented by general formula (11), mx is 0, Ar 101 Aryl groups, whether substituted or unsubstituted.
[1505] In the organic EL element involved in this embodiment,
[1506] For example, R in the first compound represented by the above general formula (1) 101 To R 110 One of them is a group represented by general formula (11), mx is 0, Ar 101 A substituted or unsubstituted heterocyclic group containing a nitrogen atom.
[1507] In the organic EL element involved in this embodiment,
[1508] For example, R in the first compound represented by the above general formula (1) 101 To R 110 One of them is a group represented by general formula (11), mx is 0, Ar 101 A substituted or unsubstituted heterocyclic group containing a sulfur atom.
[1509] In the organic EL element involved in this embodiment,
[1510] For example, R in the first compound represented by the above general formula (1) 101 To R 110 One of them is a group represented by general formula (11), mx is 0, Ar 101 For replacement or not replaced
[1511] furanyl,
[1512] Oxazolyl,
[1513] Isoxazolyl,
[1514] Oxadiazole group,
[1515] Xuton base,
[1516] Benzofuranyl,
[1517] Isobenzofuranyl,
[1518] Dibenzofuranyl,
[1519] Benzoxazolyl,
[1520] Benzisoxazole group,
[1521] phenoxazine group,
[1522] Morpholinyl,
[1523] Dinaphthylfuranyl,
[1524] Azadibenzofuranyl,
[1525] diazadibenzofuranyl,
[1526] Azanaphthalenebenzofuranyl and
[1527] Diazanaphthenebenzofuranyl.
[1528] In the organic EL element involved in this embodiment,
[1529] For example, R in the first compound represented by the above general formula (1) 101 To R 110 One of them is a group represented by general formula (11), mx is 0, Ar 101 For the sake of freedom not replaced
[1530] furanyl,
[1531] Oxazolyl,
[1532] Isoxazolyl,
[1533] Oxadiazole group,
[1534] Xuton base,
[1535] Benzofuranyl,
[1536] Isobenzofuranyl,
[1537] Dibenzofuranyl,
[1538] Benzoxazolyl,
[1539] Benzisoxazole group,
[1540] phenoxazine group,
[1541] Morpholinyl,
[1542] Dinaphthylfuranyl,
[1543] Azadibenzofuranyl,
[1544] diazadibenzofuranyl,
[1545] Azanaphthalenebenzofuranyl and
[1546] At least one group from the group consisting of diazanaphthobenzofuranyl.
[1547] In the organic EL element involved in this embodiment,
[1548] For example, R in the first compound represented by the above general formula (1) 101 To R 110 One of them is a group represented by general formula (11), mx is 0, Ar 101 It is a substituted or unsubstituted dibenzofuranyl group.
[1549] In the organic EL element involved in this embodiment,
[1550] For example, R in the first compound represented by the above general formula (1) 101 To R 110 One of them is a group represented by general formula (11), mx is 0, Ar 101 It is an unsubstituted dibenzofuranyl group.
[1551] In the organic EL element involved in this embodiment,
[1552] For example, in the first compound represented by the above general formula (101), mx is 2 or more.
[1553] In the organic EL element involved in this embodiment,
[1554] For example, in the first compound represented by the above general formula (101), mx is 1 or more, L 101 It is an arylene group with 6 to 24 carbon atoms in the ring, or a divalent heterocyclic group with 5 to 24 atoms in the ring.
[1555] In the organic EL element involved in this embodiment,
[1556] For example, in the first compound represented by the above general formula (101), mx is 1 or more, L 101 It is an arylene group with 6 to 18 carbon atoms in the ring, or a divalent heterocyclic group with 5 to 18 atoms in the ring.
[1557] In the organic EL element involved in this embodiment, it is also preferred that the first compound has at least one group represented by the following general formula (11A).
[1558]
Chemical Formula 42
[1559]
[1560] (In the above general formula (11A),
[1561] X A It consists of oxygen or sulfur atoms.
[1562] R 131 R 133 and R 134 One or more of the groups consisting of two or more adjacent elements.
[1563] They bond together to form substituted or unsubstituted monocyclic rings, or
[1564] They bond together to form substituted or unsubstituted fused rings, or
[1565] They do not bond with each other.
[1566] R 135 ~R 138 R and R that do not form the aforementioned substituted or unsubstituted monocyclic rings and do not form the aforementioned substituted or unsubstituted fused rings. 131 R 133 and R 134 Each independently
[1567] hydrogen atom,
[1568] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1569] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1570] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1571] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1572] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1573] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1574] -O-(R 904 The groups shown in the figure,
[1575] -S-(R 905 The groups shown in the figure,
[1576] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1577] -C(=O)R 801 The groups shown
[1578] -COOR 802 The groups shown
[1579] Halogen atoms,
[1580] cyano,
[1581] Nitro,
[1582] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1583] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1584] In the above general formula (11A), * indicates the bonding position with the pyrene ring in the above general formula (1).
[1585] When the first compound has at least one group represented by the above general formula (11A), it is preferable that the group is represented by the above general formula (1).
[1586] R 101 ~R 110 Each independently
[1587] hydrogen atom,
[1588] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1589] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1590] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1591] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1592] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1593] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1594] -O-(R 904 The groups shown in the figure,
[1595] -S-(R 905 The groups shown in the figure,
[1596] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1597] -C(=O)R 801 The groups shown
[1598] -COOR 802 The groups shown
[1599] Halogen atoms,
[1600] cyano,
[1601] Nitro,
[1602] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1603] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[1604] The groups represented by the above general formula (11A),
[1605] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11A) above.
[1606] When there are multiple groups represented by the above general formula (11A), the multiple groups represented by the above general formula (11A) may be the same as or different from each other.
[1607] R 135 ~R 138 They do not bond with each other to form substituted or unsubstituted monocyclic rings, nor do they form substituted or unsubstituted fused rings.
[1608] In the organic EL element involved in this embodiment, it is also preferable that the first compound has one group represented by the above general formula (11A).
[1609] In the organic EL element involved in this embodiment, R is also preferred. 101 R 103 R 106 Or R 108 The group is represented by the general formula (11A) above.
[1610] In the organic EL element involved in this embodiment, R is preferred. 135 ~R 138 for
[1611] hydrogen atom,
[1612] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1613] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1614] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1615] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1616] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1617] -Si(R 901 (R) 902 (R) 903The groups shown in the figure,
[1618] -O-(R 904 The groups shown in the figure,
[1619] -S-(R 905 The groups shown in the figure,
[1620] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1621] -C(=O)R 801 The groups shown
[1622] -COOR 802 The groups shown
[1623] Halogen atoms,
[1624] cyano, or
[1625] Nitro group.
[1626] Among the groups represented by the above general formula (11A), R is also preferred. 135 ~R 138 R and R that do not form the aforementioned substituted or unsubstituted monocyclic rings and do not form the aforementioned substituted or unsubstituted fused rings. 131 R 133 and R 134 Not a substituted or unsubstituted pyrene group, and not a group represented by the above general formula (11A) as R 101 ~R 110 The substituted or unsubstituted aryl group with 6 to 50 carbon atoms is not a substituted or unsubstituted pyrene group.
[1627] In the organic EL element involved in this embodiment, it is also preferred that the first compound has at least one group represented by the following general formula (11B).
[1628]
Chemical Formula 43
[1629]
[1630] (In the above general formula (11B),
[1631] X A It consists of oxygen or sulfur atoms.
[1632] R 131 R 133 ~R 135 R 138 and R 141 ~R 144 One or more of the groups consisting of two or more adjacent elements.
[1633] They bond together to form substituted or unsubstituted monocyclic rings, or
[1634] They bond together to form substituted or unsubstituted fused rings, or
[1635] They do not bond with each other.
[1636] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 131 R 133 ~R 135 R 138 and R 141 ~R 144 Each independently
[1637] hydrogen atom,
[1638] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1639] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1640] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1641] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1642] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1643] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1644] -O-(R 904 The groups shown in the figure,
[1645] -S-(R 905 The groups shown in the figure,
[1646] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1647] -C(=O)R 801 The groups shown
[1648] -COOR 802 The groups shown
[1649] Halogen atoms,
[1650] cyano,
[1651] Nitro,
[1652] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1653] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1654] Among them, R 135 R 138 and R 141 ~R 144 At least one of them is
[1655] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1656] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1657] In the above general formula (11B), * indicates the bonding position with the pyrene ring in the above general formula (1).
[1658] When the first compound has at least one group represented by the above general formula (11B), it is preferable to have the group represented by the above general formula (1).
[1659] R 101 ~R 110 Each independently
[1660] hydrogen atom,
[1661] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1662] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1663] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1664] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1665] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1666] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1667] -O-(R 904 The groups shown in the figure,
[1668] -S-(R 905 The groups shown in the figure,
[1669] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1670] -C(=O)R 801 The groups shown
[1671] -COOR 802 The groups shown
[1672] Halogen atoms,
[1673] cyano,
[1674] Nitro,
[1675] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1676] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[1677] The groups represented by the above general formula (11B),
[1678] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11B) above.
[1679] When there are multiple groups represented by the above general formula (11B), the multiple groups represented by the above general formula (11B) may be the same as or different from each other.
[1680] In the organic EL element involved in this embodiment, it is also preferred that the first compound has a group represented by the above general formula (11B).
[1681] In the organic EL element involved in this embodiment, R is also preferred. 101 R 103 R 106 Or R 108 The group is represented by the general formula (11B) above.
[1682] Among the groups represented by the above general formula (11B), it is preferred that R does not form the aforementioned substituted or unsubstituted monocyclic ring and does not form the aforementioned substituted or unsubstituted fused ring. 131 R 133 ~R 135 R 138 and R 141 ~R 144 Not a substituted or unsubstituted pyrene group, and not a group represented by the above general formula (11B) as R 101 ~R 110 The substituted or unsubstituted aryl group with 6 to 50 carbon atoms is not a substituted or unsubstituted pyrene group.
[1683] In the organic EL element involved in this embodiment, it is also preferred that the first compound has at least one group represented by the following general formula (11C).
[1684]
Chemical Formula 44
[1685]
[1686] (In the above general formula (11C),
[1687] X A It consists of oxygen or sulfur atoms.
[1688] R 131 R 133 R 134 R 137 R 138 and R 141 ~R 144 One or more of the groups consisting of two or more adjacent elements.
[1689] They bond together to form substituted or unsubstituted monocyclic rings, or
[1690] They bond together to form substituted or unsubstituted fused rings, or
[1691] They do not bond with each other.
[1692] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 131 R 133 R 134 R 137 R 138 and R 141 ~R 144 Each independently
[1693] hydrogen atom,
[1694] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1695] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1696] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1697] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1698] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1699] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1700] -O-(R 904 The groups shown in the figure,
[1701] -S-(R 905 The groups shown in the figure,
[1702] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1703] -C(=O)R801 The groups shown
[1704] -COOR 802 The groups shown
[1705] Halogen atoms,
[1706] cyano,
[1707] Nitro,
[1708] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1709] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1710] In the above general formula (11C), * indicates the bonding position with the pyrene ring in the above general formula (1).
[1711] When the first compound has at least one group represented by the above general formula (11C), it is preferable to have the group represented by the above general formula (1).
[1712] R 101 ~R 110 Each independently
[1713] hydrogen atom,
[1714] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1715] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1716] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1717] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1718] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1719] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1720] -O-(R 904 The groups shown in the figure,
[1721] -S-(R 905 The groups shown in the figure,
[1722] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1723] -C(=O)R 801 The groups shown
[1724] -COOR802 The groups shown
[1725] Halogen atoms,
[1726] cyano,
[1727] Nitro,
[1728] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1729] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[1730] The groups represented by the above general formula (11C),
[1731] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11C) above.
[1732] When there are multiple groups represented by the above general formula (11C), the multiple groups represented by the above general formula (11C) may be the same as or different from each other.
[1733] In the organic EL element involved in this embodiment, it is also preferred that the first compound has a group represented by the above general formula (11C).
[1734] In the organic EL element involved in this embodiment, R is also preferred. 101 R 103 R 106 Or R 108 The group is represented by the general formula (11C) above.
[1735] Among the groups represented by the above general formula (11C), it is preferred that R does not form the aforementioned substituted or unsubstituted monocyclic ring and does not form the aforementioned substituted or unsubstituted fused ring. 131 R 133 R 134 R 137 R 138 and R 141 ~R 144 Not a substituted or unsubstituted pyrene group, and not a group represented by the above general formula (11C) as R 101 ~R 110 The substituted or unsubstituted aryl group with 6 to 50 carbon atoms is not a substituted or unsubstituted pyrene group.
[1736] In the organic EL element involved in this embodiment, it is also preferred that the first compound has at least one group represented by the following general formula (11D).
[1737] [Chemical Formula 45]
[1738]
[1739] (In the above general formula (11D),
[1740] X A It consists of oxygen or sulfur atoms.
[1741] R 131 R 133 R 134 R 135 R 136 and R 141 ~R 144 One or more of the groups consisting of two or more adjacent elements.
[1742] They bond together to form substituted or unsubstituted monocyclic rings, or
[1743] They bond together to form substituted or unsubstituted fused rings, or
[1744] They do not bond with each other.
[1745] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 131 R 133 R 134 R 135 R 136 and R 141 ~R 144 Each independently
[1746] hydrogen atom,
[1747] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1748] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1749] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1750] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1751] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1752] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1753] -O-(R 904 The groups shown in the figure,
[1754] -S-(R 905 The groups shown in the figure,
[1755] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1756] -C(=O)R 801 The groups shown
[1757] -COOR 802 The groups shown
[1758] Halogen atoms,
[1759] cyano,
[1760] Nitro,
[1761] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1762] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1763] In the above general formula (11D), * indicates the bonding position with the pyrene ring in the above general formula (1).
[1764] When the first compound has at least one group represented by the above general formula (11D), it is preferable to have the group represented by the above general formula (1).
[1765] R 101 ~R 110 Each independently
[1766] hydrogen atom,
[1767] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1768] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1769] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1770] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1771] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1772] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1773] -O-(R 904 The groups shown in the figure,
[1774] -S-(R 905 The groups shown in the figure,
[1775] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1776] -C(=O)R 801 The groups shown
[1777] -COOR 802 The groups shown
[1778] Halogen atoms,
[1779] cyano,
[1780] Nitro,
[1781] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1782] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[1783] The groups represented by the above general formula (11D),
[1784] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11D) above.
[1785] When there are multiple groups represented by the above general formula (11D), the multiple groups represented by the above general formula (11D) may be the same as or different from each other.
[1786] In the organic EL element involved in this embodiment, it is also preferred that the first compound has a group represented by the above general formula (11D).
[1787] In the organic EL element involved in this embodiment, R is also preferred. 101 R 103 R 106 Or R 108 The group is represented by the general formula (11D) above.
[1788] Among the groups represented by the above general formula (11D), it is preferred that R does not form the aforementioned substituted or unsubstituted monocyclic ring and does not form the aforementioned substituted or unsubstituted fused ring. 131 R 133 R 134 R 135 R 136 and R 141 ~R 144 Not a substituted or unsubstituted pyrene group, and not a group represented by the above general formula (11D) as R 101 ~R 110 The substituted or unsubstituted aryl group with 6 to 50 carbon atoms is not a substituted or unsubstituted pyrene group.
[1789] In the organic EL element involved in this embodiment, it is also preferred that the first compound has at least one group represented by the following general formula (11E).
[1790]
Chemical Formula 46
[1791]
[1792] (In the above general formula (11E),
[1793] X A It consists of oxygen or sulfur atoms.
[1794] R 131 R 133 ~R 135 R 138 and R 141 ~R 144 One or more of the groups consisting of two or more adjacent elements.
[1795] They bond together to form substituted or unsubstituted monocyclic rings, or
[1796] They bond together to form substituted or unsubstituted fused rings, or
[1797] They do not bond with each other.
[1798] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 131 R 133 ~R 135 R 138 and R 141 ~R 144 Each independently
[1799] hydrogen atom,
[1800] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1801] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1802] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1803] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1804] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1805] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1806] -O-(R 904 The groups shown in the figure,
[1807] -S-(R 905The groups shown in the figure,
[1808] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1809] -C(=O)R 801 The groups shown
[1810] -COOR 802 The groups shown
[1811] Halogen atoms,
[1812] cyano,
[1813] Nitro,
[1814] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1815] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1816] L 101 for
[1817] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1818] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1819] mx is 1, 2, 3, 4 or 5.
[1820] In L 101 When there are more than two, more than two L 101 They are the same or different.
[1821] In the above general formula (11E), * indicates the bonding position with the pyrene ring in the above general formula (1).
[1822] When the first compound has at least one group represented by the above general formula (11E), it is preferable to have the group represented by the above general formula (1).
[1823] R 101 ~R 110 Each independently
[1824] hydrogen atom,
[1825] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1826] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1827] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1828] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1829] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1830] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1831] -O-(R 904 The groups shown in the figure,
[1832] -S-(R 905 The groups shown in the figure,
[1833] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1834] -C(=O)R 801 The groups shown
[1835] -COOR 802 The groups shown
[1836] Halogen atoms,
[1837] cyano,
[1838] Nitro,
[1839] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1840] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[1841] The groups represented by the above general formula (11E),
[1842] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11E) above.
[1843] When there are multiple groups represented by the above general formula (11E), the multiple groups represented by the above general formula (11E) may be the same as or different from each other.
[1844] In the organic EL element involved in this embodiment, it is also preferred that the first compound has a group represented by the above general formula (11E).
[1845] In the organic EL element involved in this embodiment, R is also preferred. 101 R 103 R 106 Or R 108 The group is represented by the general formula (11E) above.
[1846] Among the groups represented by the above general formula (11E), it is preferred that R does not form the aforementioned substituted or unsubstituted monocyclic ring and does not form the aforementioned substituted or unsubstituted fused ring. 131 R 133 ~R 135 R 138 and R 141 ~R 144 Not a substituted or unsubstituted pyrene group, not a group represented by the above general formula (11E) as R 101 ~R 110 The substituted or unsubstituted aryl group with 6 to 50 carbon atoms is not a substituted or unsubstituted pyrene group.
[1847] In the organic EL element involved in this embodiment, it is also preferred that the group shown in the above general formula (11) is the group shown in the following general formula (111E).
[1848] [Chemical Formula 47]
[1849]
[1850] (In the above general formula (111E),
[1851] X1 is CR 123 R 124 oxygen atom, sulfur atom or NR 125 ,
[1852] L 111 and L 112 Each independently
[1853] single bond,
[1854] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1855] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1856] ma is 1, 2, 3, or 4.
[1857] mb is 1, 2, 3, or 4.
[1858] ma+mb is 2, 3, or 4.
[1859] X A R 131 R 133 ~R 135 R 138 and R 141 ~R 144 respectively with X in the above general formula (11E) A R 131 R 133 ~R135 R 138 and R 141 ~R 144 Same meaning
[1860] R 121 R 122 R 123 R 124 and R 125 Each independently
[1861] hydrogen atom,
[1862] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1863] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1864] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1865] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1866] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1867] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1868] -O-(R 904 The groups shown in the figure,
[1869] -S-(R 905 The groups shown in the figure,
[1870] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1871] -C(=O)R 801 The groups shown
[1872] -COOR 802 The groups shown
[1873] Halogen atoms,
[1874] cyano,
[1875] Nitro,
[1876] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1877] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1878] mc is 3.
[1879] 3 Rs121 They are the same or different.
[1880] md is 3
[1881] 3 Rs 122 (They may be the same or different.)
[1882] In the organic EL element involved in this embodiment, it is preferred that ma is 1 or 2 and mb is 1 or 2.
[1883] In the organic EL element involved in this embodiment, it is preferred that ma is 1 and mb is 1.
[1884] In the organic EL element involved in this embodiment, it is preferable that the R group is not represented by the groups shown in the above general formulas (11A), (11B), (11C), (11D), (11E), or (111E). 101 ~R 110 Each independently
[1885] hydrogen atom,
[1886] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1887] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1888] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1889] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1890] In the organic EL element involved in this embodiment, it is preferable that the R group is not represented by the groups shown in the above general formulas (11A), (11B), (11C), (11D), (11E), or (111E). 101 ~R 110 Each independently
[1891] hydrogen atom,
[1892] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[1893] Cycloalkyl groups, substituted or unsubstituted, having 3 to 50 carbon atoms.
[1894] In the organic EL element involved in this embodiment, the R group is not one of the groups shown in general formulas (11A), (11B), (11C), (11D), (11E), or (111E). 101 ~R 110 Hydrogen atoms are preferred.
[1895] (Method for manufacturing the first compound)
[1896] The first compound can be manufactured using known methods. Alternatively, the first compound can also be manufactured using known alternative reactions and starting materials corresponding to the target substance, following the same known methods.
[1897] (Specific examples of the first compound)
[1898] Specific examples of the first compound include the following compounds. However, the present invention is not limited to these specific examples of the first compound.
[1899] [Chemical Formula 48]
[1900]
[1901] [Chemical Formula 49]
[1902]
[1903] [Chemical Formula 50]
[1904]
[1905]
Chemical Formula 51
[1906]
[1907]
Chemical Formula 52
[1908]
[1909]
Chemical Formula 53
[1910]
[1911] [Chemical Formula 54]
[1912]
[1913]
Chemical Formula 55
[1914]
[1915] [Chemical Formula 56]
[1916]
[1917] [Chemical Formula 57]
[1918]
[1919] [Chemical Formula 58]
[1920]
[1921] [Chemical Formula 59]
[1922]
[1923] [Chemical Formula 60]
[1924]
[1925]
Chemical Formula 61
[1926]
[1927]
Chemical Formula 62
[1928]
[1929]
Chemical Formula 63
[1930]
[1931]
Chemical Formula 64
[1932]
[1933]
Chemical Formula 65
[1934]
[1935] (Second compound)
[1936] In the organic EL element involved in this embodiment, the second compound is the compound shown in the following general formula (2).
[1937]
Chemical Formula 66
[1938]
[1939] (In the above general formula (2),)
[1940] R 201 ~R 208 Each independently
[1941] hydrogen atom,
[1942] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1943] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1944] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1945] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1946] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1947] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1948] -O-(R 904 The groups shown in the figure,
[1949] -S-(R 905 The groups shown in the figure,
[1950] -N(R 906 (R) 907 The groups shown in the figure,
[1951] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1952] -C(=O)R 801 The groups shown
[1953] -COOR 802 The groups shown
[1954] Halogen atoms,
[1955] cyano,
[1956] Nitro,
[1957] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1958] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1959] L 201 and L 202 Each independently
[1960] single bond,
[1961] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1962] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1963] Ar 201 and Ar 202 Each independently
[1964] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1965] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[1966] (In the second compound involved in this embodiment, R)901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently
[1967] hydrogen atom,
[1968] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1969] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1970] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1971] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1972] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[1973] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[1974] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.
[1975] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
[1976] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.
[1977] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.
[1978] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.
[1979] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[1980] In R 802In the case of multiple Rs, multiple Rs 802 (They may be the same or different.)
[1981] In the organic EL element involved in this embodiment, it is preferred that,
[1982] R 201 ~R 208 Each independently
[1983] hydrogen atom,
[1984] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1985] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1986] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1987] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1988] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1989] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1990] -O-(R 904 The groups shown in the figure,
[1991] -S-(R 905 The groups shown in the figure,
[1992] -N(R 906 (R) 907 The groups shown in the figure,
[1993] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1994] -C(=O)R 801 The groups shown
[1995] -COOR 802 The groups shown
[1996] Halogen atoms,
[1997] cyano, or
[1998] Nitro,
[1999] L 201 and L 202 Each independently
[2000] single bond,
[2001] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[2002] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2003] Ar 201 and Ar 202 Each independently
[2004] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2005] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[2006] In the organic EL element involved in this embodiment, it is preferred that,
[2007] L 201 and L 202 Each independently
[2008] single key or
[2009] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms in a cyclic structure.
[2010] Ar 201 and Ar 202 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure.
[2011] In the organic EL element involved in this embodiment, it is preferred that,
[2012] Ar 201 and Ar 202 Each independently
[2013] Phenyl,
[2014] Naphthyl,
[2015] Fiki,
[2016] Biphenyl,
[2017] Triphenyl
[2018] Diphenylfluorenyl,
[2019] Dimethylfluorene,
[2020] benzodiphenylfluorenyl,
[2021] benzodimethylfluorenyl,
[2022] Dibenzofuranyl,
[2023] Dibenzothiophene group,
[2024] Naphthobenzofuranyl, or
[2025] Naphthobenzothiophene group.
[2026] In the organic EL element of this embodiment, the second compound represented by the above general formula (2) is preferably a compound represented by the following general formulas (201), (202), (203), (204), (205), (206), (207), (208), or (209).
[2027] [Chemical Formula 67]
[2028]
[2029]
Chemical Formula 68
[2030]
[2031]
Chemical Formula 69
[2032]
[2033] [Chemical Formula 70]
[2034]
[2035]
Chemical Formula 71
[2036]
[2037]
Chemical Formula 72
[2038]
[2039]
Chemical Formula 73
[2040]
[2041] [Chemical Formula 74]
[2042]
[2043] [Chemical Formula 75]
[2044]
[2045] (In the above general formulas (201) to (209),
[2046] L 201 and Ar 201 L in the above general formula (2) 201 and Ar 201 Same meaning
[2047] R 201 ~R208 Each independently relates to R in the above general formula (2) 201 ~R 208 The meaning is the same.
[2048] The second compound represented by the above general formula (2) is also preferably a compound represented by the following general formulas (221), (222), (223), (224), (225), (226), (227), (228) or (229).
[2049] [Chemical Formula 76]
[2050]
[2051]
Chemical Formula 77
[2052]
[2053] [Chemical Formula 78]
[2054]
[2055] [Chemical Formula 79]
[2056]
[2057] [Chemical Formula 80]
[2058]
[2059]
Chemical Formula 81
[2060]
[2061]
Chemical Formula 82
[2062]
[2063]
Chemical Formula 83
[2064]
[2065]
Chemical Formula 84
[2066]
[2067] (In the above general formulas (221), (222), (223), (224), (225), (226), (227), (228), and (229),
[2068] R 201 and R 203 ~R208 Each independently relates to R in the above general formula (2) 201 and R 203 ~R 208 Same meaning
[2069] L 201 and Ar 201 Each of the above general formulas (2) with L 201 and Ar 201 Same meaning
[2070] L 203 L in the above general formula (2) 201 Same meaning
[2071] L 203 With L 201 They are the same or different.
[2072] Ar 203 Ar in the above general formula (2) 201 Same meaning
[2073] Ar 203 with Ar 201 (They may be the same or different.)
[2074] The second compound represented by the above general formula (2) is also preferably a compound represented by the following general formulas (241), (242), (243), (244), (245), (246), (247), (248) or (249).
[2075]
Chemical Formula 85
[2076]
[2077]
Chemical Formula 86
[2078]
[2079] [Chemical Formula 87]
[2080]
[2081]
Chemical Formula 88
[2082]
[2083]
Chemical Formula 89
[2084]
[2085] [Chemical Formula 90]
[2086]
[2087]
Chemical Formula 91
[2088]
[2089]
Chemical Formula 92
[2090]
[2091] [Chemical Formula 93]
[2092]
[2093] (In the above general formulas (241), (242), (243), (244), (245), (246), (247), (248), and (249),
[2094] R 201 R 202 and R 204 ~R 208 Each independently relates to R in the above general formula (2) 201 R 202 and R 204 ~R 208 Same meaning
[2095] L 203 L in the above general formula (2) 201 Same meaning
[2096] L 203 With L 201 They are the same or different.
[2097] Ar 203 Ar in the above general formula (2) 201 Same meaning
[2098] Ar 203 with Ar 201 (They may be the same or different.)
[2099] In the second compound represented by the above general formula (2), it is preferable that the R group is not represented by the group represented by the above general formula (21). 201 ~R 208 Each independently
[2100] hydrogen atom,
[2101] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2102] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or
[2103] -Si(R 901 (R) 902 (R) 903 The group shown is ).
[2104] Preferably, L 101 for
[2105] single key or
[2106] Unsubstituted arylene groups with 6 to 22 carbon atoms in the cyclic group,
[2107] Ar 101 It is an aryl group with 6 to 22 carbon atoms, either substituted or unsubstituted.
[2108] In the organic EL element involved in this embodiment, in the second compound shown by the above general formula (2), R, as a substituent of the anthracene skeleton, 201 ~R 208 From the perspective of preventing the suppression of intermolecular interactions and inhibiting the decrease in electron mobility, hydrogen atoms are preferred, R 201 ~R 208 It can also be an aryl group with 6 to 50 cyclic carbon atoms, substituted or unsubstituted, or a heterocyclic group with 5 to 50 cyclic atoms.
[2109] R 201 ~R 208 When the substituents are sterically hindered, such as alkyl and cycloalkyl groups, intermolecular interactions are suppressed, and the electron mobility decreases relative to the first compound, potentially violating the μH2>μH1 relationship described in the following mathematical formula (Formula 3). When the second compound is used in the second luminescent layer, it is expected that the decrease in the recombination ability of holes and electrons in the first luminescent layer and the decrease in luminous efficiency can be suppressed by satisfying the μH2>μH1 relationship. It should be noted that as substituents, alkyl halogens, alkenyl groups, alkynyl groups, and -Si(R) are suitable. 901 (R) 902 (R) 903 The group shown is -O-(R) 904 The group shown is -S-(R) 905 The group shown is -N(R) 906 (R) 907 The groups shown are aralkyl groups, -C(=O)R 801 The indicated group, -COOR 802 The groups, halogen atoms, cyano groups, and nitro groups shown may form high steric hindrance, while alkyl and cycloalkyl groups may form even higher steric hindrance.
[2110] In the second compound represented by the above general formula (2), R, as a substituent of the anthracene skeleton,201 ~R 208 Preferably, the substituent is not a highly sterically hindered substituent; preferably, it is not alkyl or cycloalkyl; more preferably, it is not alkyl, cycloalkyl, haloalkyl, alkenyl, alkynyl, or -Si(R) 901 (R) 902 (R) 903 The group shown is -O-(R) 904 The group shown is -S-(R) 905 The group shown is -N(R) 906 (R) 907 The groups shown are aralkyl groups, -C(=O)R 801 The indicated group, -COOR 802 The groups shown include halogen atoms, cyano groups, and nitro groups.
[2111] In the organic EL element involved in this embodiment,
[2112] In the second compound shown by the above general formula (2), R is also preferred. 201 ~R 208 Each independently
[2113] hydrogen atom,
[2114] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2115] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or
[2116] -Si(R 901 (R) 902 (R) 903 The group shown is ).
[2117] In the organic EL element involved in this embodiment,
[2118] In the second compound represented by the above general formula (2), R 201 ~R 208 Hydrogen atoms are preferred.
[2119] In the second compound mentioned above, R 201 ~R 208 When the expression "substituted or unsubstituted" is used, the substituents preferably do not include the substituents that may form high steric hindrance, especially substituted or unsubstituted alkyl groups and substituted or unsubstituted cycloalkyl groups. R 201 ~R 208When the substituent is described as "substituted or unsubstituted", it prevents the intermolecular interactions caused by the presence of highly sterically hindered substituents such as alkyl and cycloalkyl groups from being suppressed by not containing substituted or unsubstituted alkyl groups or substituted or unsubstituted cycloalkyl groups. This prevents the decrease in electron mobility. In addition, when such a second compound is used in the second light-emitting layer, it can suppress the decrease in the recombination ability of holes and electrons in the first light-emitting layer and the decrease in luminous efficiency.
[2120] Further preferred R as a substituent for the anthracene skeleton 201 ~R 208 It is not a sterically hindered substituent, but rather R as a substituent. 201 ~R 208 It is unsubstituted. Additionally, R, as a substituent in the anthracene skeleton... 201 ~R 208 In cases where the substituent is not highly sterically hindered, R acts as a substituent with low steric hindrance. 201 ~R 208 In the case of top-bonded substituents, these substituents are preferably not sterically hindered substituents, and R as a substituent... 201 ~R 208 The substituent bonded above is preferably not alkyl or cycloalkyl, more preferably not alkyl, cycloalkyl, haloalkyl, alkenyl, ynyl, or -Si(R) 901 (R) 902 (R) 903 The group shown is -O-(R) 904 The group shown is -S-(R) 905 The group shown is -N(R) 906 (R) 907 The groups shown are aralkyl groups, -C(=O)R 801 The indicated group, -COOR 802 The groups shown include halogen atoms, cyano groups, and nitro groups.
[2121] In the second compound described above, the groups described as "substituted or unsubstituted" are preferably "unsubstituted".
[2122] In the organic EL element involved in this embodiment, for example, Ar in the second compound shown in the above general formula (2) 201 It is a substituted or unsubstituted dibenzofuranyl group.
[2123] In the organic EL element involved in this embodiment, for example, Ar in the second compound shown in the above general formula (2) 201 It is an unsubstituted dibenzofuranyl group.
[2124] In the organic EL element involved in this embodiment, for example, the second compound shown in the above general formula (2) has at least one hydrogen, of which at least one is deuterium.
[2125] In the organic EL element involved in this embodiment, for example, L in the second compound shown in the above general formula (2) 201 The range is from TEMP-63 to TEMP-68.
[2126] [Chemical Formula 94]
[2127]
[2128] In the organic EL element involved in this embodiment, for example, Ar in the second compound shown in the above general formula (2) 201 To choose freely to replace or not to replace
[2129] anthracene,
[2130] Benzanthracene,
[2131] Fiki,
[2132] Benzphenanthrene,
[2133] Finadenyl,
[2134] Pyrene
[2135] base,
[2136] benzo[a] base,
[2137] Tri-phenylene,
[2138] Benzotrimethylene
[2139] phenylene,
[2140] Pentaphenyl,
[2141] Fluoranthene base,
[2142] Benzofluoranthyl and
[2143] At least one group in the group consisting of perylene groups.
[2144] In the organic EL element involved in this embodiment, for example, Ar in the second compound shown in the above general formula (2) 201 The fluorene group can be substituted or unsubstituted.
[2145] In the organic EL element involved in this embodiment, for example, Ar in the second compound shown in the above general formula (2) 201 For substituted or unsubstituted thallium groups.
[2146] In the organic EL element involved in this embodiment, for example, Ar2 in the second compound shown in the above general formula (2) 01 It is benzoxanthryl.
[2147] (Method for manufacturing the second compound)
[2148] The second compound can be manufactured using known methods. Alternatively, the second compound can also be manufactured by following known methods, using known alternative reactions and starting materials corresponding to the target substance.
[2149] (Specific example of the second compound)
[2150] Specific examples of the second compound include the following compounds. However, the present invention is not limited to these specific examples of the second compound.
[2151] [Chemical Formula 95]
[2152]
[2153]
Chemical Formula 96
[2154]
[2155] [Chemical Formula 97]
[2156]
[2157] [Chemical Formula 98]
[2158]
[2159]
Chemical Formula 99
[2160]
[2161]
Chemical Formula 100
[2162]
[2163]
Chemical Formula 101
[2164]
[2165]
Chemical Formula 102
[2166]
[2167]
Chemical Formula 103
[2168]
[2169] [Chemical Formula 104]
[2170]
[2171] [Chemical Formula 105]
[2172]
[2173] [Chemical Formula 106]
[2174]
[2175] [Chemical Formula 107]
[2176]
[2177] [Chemical Formula 108]
[2178]
[2179] [Chemical Formula 109]
[2180]
[2181]
Chemical Formula 110
[2182]
[2183]
Chemical Formula 111
[2184]
[2185]
Chemical Formula 112
[2186]
[2187]
Chemical Formula 113
[2188]
[2189]
Chemical Formula 114
[2190]
[2191]
Chemical Formula 115
[2192]
[2193]
Chemical Formula 116
[2194]
[2195]
Chemical Formula 117
[2196]
[2197]
Chemical Formula 118
[2198]
[2199]
Chemical Formula 119
[2200]
[2201]
Chemical Formula 120
[2202]
[2203]
Chemical Formula 121
[2204]
[2205]
Chemical Formula 122
[2206]
[2207]
Chemical Formula 123
[2208]
[2209] [Chemical Formula 124]
[2210]
[2211] [Chemical Formula 125]
[2212]
[2213] [Chemical Formula 126]
[2214]
[2215]
Chemical Formula 127
[2216]
[2217] [Chemical Formula 128]
[2218]
[2219] [Chemical Formula 129]
[2220]
[2221]
Chemical Formula 130
[2222]
[2223]
Chemical Formula 131
[2224]
[2225]
Chemical Formula 132
[2226]
[2227]
Chemical Formula 133
[2228]
[2229]
Chemical Formula 134
[2230]
[2231] [Chemical Formula 135]
[2232]
[2233]
Chemical Formula 136
[2234]
[2235] (Compound 3 and Compound 4)
[2236] In the organic EL element involved in this embodiment, it is also preferable that the first light-emitting layer further contains a third compound with fluorescent properties.
[2237] In the organic EL element involved in this embodiment, it is also preferable that the second light-emitting layer further contains a fourth compound with fluorescent properties.
[2238] In the case where the first luminescent layer contains a third compound and the second luminescent layer contains a fourth compound, the third compound and the fourth compound may be the same as or different from each other.
[2239] The third and fourth compounds are each independently selected.
[2240] The compounds represented by the following general formula (3),
[2241] The compounds represented by the following general formula (4),
[2242] The compounds represented by the following general formula (5),
[2243] The compounds represented by the following general formula (6),
[2244] The compounds represented by the following general formula (7),
[2245] The compounds represented by the following general formula (8),
[2246] The compounds represented by the following general formula (9) and
[2247] One or more compounds in the group consisting of compounds represented by the general formula (10) below.
[2248] (The compound represented by general formula (3))
[2249] The compounds represented by general formula (3) will be described.
[2250]
Chemical Formula 137
[2251]
[2252] (In the above general formula (3),
[2253] R 301 ~R 310 One or more of the groups consisting of two or more adjacent elements.
[2254] They bond together to form substituted or unsubstituted monocyclic rings, or
[2255] They bond together to form substituted or unsubstituted fused rings, or
[2256] They do not bond with each other.
[2257] R 301 ~R 310 At least one of them is a monovalent group represented by the following general formula (31),
[2258] R that does not form the above-mentioned monocyclic ring, does not form the above-mentioned fused ring, and is not a monovalent group represented by the following general formula (31) 301 ~R 310 Each independently
[2259] hydrogen atom,
[2260] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2261] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2262] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2263] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2264] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2265] -O-(R 904 The groups shown in the figure,
[2266] -S-(R 905 The groups shown in the figure,
[2267] -N(R 906 (R) 907 The groups shown in the figure,
[2268] Halogen atoms,
[2269] cyano,
[2270] Nitro,
[2271] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2272] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[2273]
Chemical Formula 138
[2274]
[2275] (In the above general formula (31),
[2276] Ar 301 and Ar 302 Each independently
[2277] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2278] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2279] L 301 ~L 303 Each independently
[2280] single bond,
[2281] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or
[2282] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.
[2283] * indicates the bonding position in the pyrene ring in the above general formula (3).
[2284] In the third and fourth compounds, R 901 R 902 R 903 R 904 R 905 R 906 and R 907 Each independently
[2285] hydrogen atom,
[2286] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2287] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2288] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2289] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2290] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[2291] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[2292] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[2293] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[2294] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.
[2295] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
[2296] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.
[2297] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.
[2298] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.
[2299] In the above general formula (3), R is preferred. 301 ~R 310 Two of them are groups represented by the general formula (31) above.
[2300] In one embodiment, the compound represented by the above general formula (3) is the compound represented by the following general formula (33).
[2301]
Chemical Formula 139
[2302]
[2303] (In the above general formula (33),
[2304] R 311 ~R 318 Each independently interacts with the R group in the above general formula (3) that is not a monovalent group represented by the above general formula (31). 301 ~R 310 Same meaning
[2305] L 311 ~L 316 Each independently
[2306] single bond,
[2307] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or
[2308] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.
[2309] Ar 312 Ar 313 Ar 315 and Ar 316 Each independently
[2310] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2311] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2312] In the above general formula (31), L 301 Preferably a single bond, L 302 and L 303 Single bonds are preferred.
[2313] In one embodiment, the compound represented by the above general formula (3) is represented by the following general formula (34) or general formula (35).
[2314] [Chemical Formula 140]
[2315]
[2316] (In the above general formula (34),
[2317] R 311 ~R 318 Each independently interacts with the R group in the above general formula (3) that is not a monovalent group represented by the above general formula (31). 301 ~R 310 Same meaning
[2318] L 312 L 313 L 315 and L 316 Each independently relates to L in the above general formula (33) 312 L313 L 315 and L 316 Same meaning
[2319] Ar 312 Ar 313 Ar 315 and Ar 316 Each independently relates to Ar in the above general formula (33) 312 Ar 313 Ar 315 and Ar 316 The meaning is the same.
[2320]
Chemical Formula 141
[2321]
[2322] (In the above general formula (35),
[2323] R 311 ~R 318 Each independently interacts with the R group in the above general formula (3) that is not a monovalent group represented by the above general formula (31). 301 ~R 310 Same meaning
[2324] Ar 312 Ar 313 Ar 315 and Ar 316 Each independently relates to Ar in the above general formula (33) 312 Ar 313 Ar 315 and Ar 316 The meaning is the same.
[2325] In the above general formula (31), it is preferred that Ar 301 and Ar 302 At least one of them is a group represented by the following general formula (36).
[2326] In the above general formulas (33) to (35), Ar is preferred. 312 and Ar 313 At least one of them is a group represented by the following general formula (36).
[2327] In the above general formulas (33) to (35), Ar is preferred. 315 and Ar 316 At least one of them is a group represented by the following general formula (36).
[2328] [Chemical Formula 142]
[2329]
[2330] (In the above general formula (36),
[2331] X3 represents an oxygen atom or a sulfur atom.
[2332] R 321 ~R 327 One or more of the groups consisting of two or more adjacent elements.
[2333] They bond together to form substituted or unsubstituted monocyclic rings, or
[2334] They bond together to form substituted or unsubstituted fused rings, or
[2335] They do not bond with each other.
[2336] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 321 ~R 327 Each independently
[2337] hydrogen atom,
[2338] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2339] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2340] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2341] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2342] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2343] -O-(R 904 The groups shown in the figure,
[2344] -S-(R 905 The groups shown in the figure,
[2345] -N(R 906 (R) 907 The groups shown in the figure,
[2346] Halogen atoms,
[2347] cyano,
[2348] Nitro,
[2349] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2350] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2351] * indicates that L 302 L 303 L 312 L 313 L 315 or L 316 (The bonding location.)
[2352] X3 is preferably an oxygen atom.
[2353] Preferred R 321 ~R 327 At least one of them is
[2354] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2355] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2356] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2357] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2358] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2359] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[2360] In the above general formula (31), it is preferred that Ar 301 For the group represented by the above general formula (36), Ar 302 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.
[2361] In the above general formulas (33) to (35), Ar is preferred. 312 For the group represented by the above general formula (36), Ar 313 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.
[2362] In the above general formulas (33) to (35), Ar is preferred. 315 For the group represented by the above general formula (36), Ar 316 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.
[2363] In one embodiment, the compound represented by the above general formula (3) is represented by the following general formula (37).
[2364] [Chemical Formula 143]
[2365]
[2366] (In the above general formula (37),
[2367] R 311 ~R 318 Each independently interacts with the R group in the above general formula (3) that is not a monovalent group represented by the above general formula (31). 301 ~R 310 Same meaning
[2368] R 321 ~R 327 One or more of the groups consisting of two or more adjacent elements.
[2369] They bond together to form substituted or unsubstituted monocyclic rings, or
[2370] They bond together to form substituted or unsubstituted fused rings, or
[2371] They do not bond with each other.
[2372] R 341 ~R 347 One or more of the groups consisting of two or more adjacent elements.
[2373] They bond together to form substituted or unsubstituted monocyclic rings, or
[2374] They bond together to form substituted or unsubstituted fused rings, or
[2375] They do not bond with each other.
[2376] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 321 ~R 327 and R 341 ~R 347 Each independently
[2377] hydrogen atom,
[2378] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2379] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2380] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2381] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2382] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2383] -O-(R 904 The groups shown in the figure,
[2384] -S-(R 905 The groups shown in the figure,
[2385] -N(R 906 (R) 907 The groups shown in the figure,
[2386] Halogen atoms,
[2387] cyano,
[2388] Nitro,
[2389] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2390] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2391] R 331 ~R 335 and R 351 ~R 355 Each independently
[2392] hydrogen atom,
[2393] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2394] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2395] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2396] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2397] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2398] -O-(R 904 The groups shown in the figure,
[2399] -S-(R 905 The groups shown in the figure,
[2400] -N(R 906 (R) 907 The groups shown in the figure,
[2401] Halogen atom, cyano group, nitro group,
[2402] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2403] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2404] As a compound represented by the general formula (3) above, the following compounds can be cited as specific examples.
[2405] [Chemical Formula 144]
[2406]
[2407] [Chemical Formula 145]
[2408]
[2409] [Chemical Formula 146]
[2410]
[2411] [Chemical Formula 147]
[2412]
[2413] [Chemical Formula 148]
[2414]
[2415] (The compound represented by general formula (4))
[2416] The compounds represented by general formula (4) will be described.
[2417] [Chemical Formula 149]
[2418]
[2419] (In the above general formula (4),
[2420] Z can be independently represented by CRa or nitrogen atoms.
[2421] Rings A1 and A2 are each independent of each other.
[2422] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or
[2423] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2424] When there are multiple Ra, one or more groups consisting of two or more adjacent Ra are selected.
[2425] They bond together to form substituted or unsubstituted monocyclic rings, or
[2426] They bond together to form substituted or unsubstituted fused rings, or
[2427] They do not bond with each other.
[2428] n21 and n22 are each independently 0, 1, 2, 3 or 4.
[2429] When there are multiple Rb, one or more groups consisting of two or more adjacent Rb are considered.
[2430] They bond together to form substituted or unsubstituted monocyclic rings, or
[2431] They bond together to form substituted or unsubstituted fused rings, or
[2432] They do not bond with each other.
[2433] When there are multiple Rc, one or more groups are formed by two or more adjacent Rc.
[2434] They bond together to form substituted or unsubstituted monocyclic rings, or
[2435] They bond together to form substituted or unsubstituted fused rings, or
[2436] They do not bond with each other.
[2437] Ra, Rb, and Rc, which do not form the aforementioned single rings and do not form the aforementioned fused rings, are each independently...
[2438] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2439] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2440] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2441] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2442] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2443] -O-(R 904 The groups shown in the figure,
[2444] -S-(R 905 The groups shown in the figure,
[2445] -N(R 906 (R) 907 The groups shown in the figure,
[2446] Halogen atoms,
[2447] cyano,
[2448] Nitro,
[2449] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2450] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2451] The "aromatic hydrocarbon rings" of the A1 and A2 rings have the same structure as compounds formed by introducing hydrogen atoms into the aforementioned "aryl" group.
[2452] The "aromatic hydrocarbon rings" of A1 and A2 rings contain two carbon atoms on the fused 2-ring structure in the center of the above general formula (4) as cyclic atoms.
[2453] As a specific example of "a cyclic aromatic hydrocarbon ring with 6 to 50 carbon atoms, whether substituted or unsubstituted", compounds formed by introducing hydrogen atoms into the "aryl" group described in Specific Example Group G1 can be cited.
[2454] The "heterocyclic" rings A1 and A2 have the same structure as compounds formed by introducing hydrogen atoms into the aforementioned "heterocyclic group".
[2455] The "heterocyclic" rings A1 and A2 contain two carbon atoms on the fused 2-ring structure in the center of the above general formula (4) as cyclic atoms.
[2456] As a specific example of "a heterocycle with 5 to 50 cyclic atoms, whether substituted or unsubstituted", one can cite compounds formed by introducing hydrogen atoms into the "heterocyclic group" described in Specific Example Group G2.
[2457] Rb is bonded to any of the carbon atoms that form an aromatic hydrocarbon ring as an A1 ring, or to any of the atoms that form a heterocycle as an A1 ring.
[2458] Rc is bonded to any one of the carbon atoms that form an aromatic hydrocarbon ring as an A2 ring, or to any one of the atoms that form a heterocycle as an A2 ring.
[2459] Among Ra, Rb and Rc, at least one is preferably a group represented by the following general formula (4a), and more preferably at least two are groups represented by the following general formula (4a).
[2460] [Chemical Formula 150]
[2461] *-L 401 -Ar 401 (4a)
[2462] (In the above general formula (4a),
[2463] L 401 for
[2464] single bond,
[2465] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or
[2466] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.
[2467] Ar 401 for
[2468] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[2469] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[2470] The group represented by the following general formula (4b).
[2471]
Chemical Formula 151
[2472]
[2473] (In the above general formula (4b),
[2474] L 402 and L 403 Each independently
[2475] single bond,
[2476] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or
[2477] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.
[2478] Ar 402 and Ar 403 The group formed
[2479] They bond together to form substituted or unsubstituted monocyclic rings, or
[2480] They bond together to form substituted or unsubstituted fused rings, or
[2481] They do not bond with each other.
[2482] Ar does not form the aforementioned single ring and does not form the aforementioned fused ring 402 and Ar 403 Each independently
[2483] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2484] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2485] In one embodiment, the compound represented by the above general formula (4) is represented by the following general formula (42).
[2486]
Chemical Formula 152
[2487]
[2488] (In the above general formula (42),
[2489] R 401 ~R 411 One or more of the groups consisting of two or more adjacent elements.
[2490] They bond together to form substituted or unsubstituted monocyclic rings, or
[2491] They bond together to form substituted or unsubstituted fused rings, or
[2492] They do not bond with each other.
[2493] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 401 ~R 411 Each independently
[2494] hydrogen atom,
[2495] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2496] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2497] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2498] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2499] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2500] -O-(R 904 The groups shown in the figure,
[2501] -S-(R 905 The groups shown in the figure,
[2502] -N(R 906 (R) 907 The groups shown in the figure,
[2503] Halogen atoms,
[2504] cyano,
[2505] Nitro,
[2506] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2507] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2508] R 401 ~R 411Preferably, at least one of them is a group represented by the above general formula (4a), and more preferably at least two of them are groups represented by the above general formula (4a).
[2509] R 404 and R 411 Preferably, it is a group represented by the above general formula (4a).
[2510] In one embodiment, the compound represented by the above general formula (4) is a compound formed by bonding the structure represented by the following general formula (4-1) or general formula (4-2) onto the A1 ring.
[2511] Additionally, in one embodiment, the compound represented by the above general formula (42) is in R 404 ~R 407 Compounds formed by bonding the following general formula (4-1) or general formula (4-2) to the bonded ring.
[2512]
Chemical Formula 153
[2513]
[2514] In the above general formula (4-1), each of the two * is independently bonded to the cyclic carbon atom of the aromatic hydrocarbon ring or the cyclic atom of the heterocycle in the above general formula (4), or to the R in the above general formula (42). 404 ~R 407 Any one of the bonds in,
[2515] The three asterisks in the above general formula (4-2) are each independently bonded to the cyclic carbon atom of the aromatic hydrocarbon ring or the cyclic atom of the heterocycle in the above general formula (4), or to the R in the above general formula (42). 404 ~R 407 Any one of the bonds in,
[2516] R 421 ~R 427 One or more of the groups consisting of two or more adjacent elements.
[2517] They bond together to form substituted or unsubstituted monocyclic rings, or
[2518] They bond together to form substituted or unsubstituted fused rings, or
[2519] They do not bond with each other.
[2520] R 431 ~R 438 One or more of the groups consisting of two or more adjacent elements.
[2521] They bond together to form substituted or unsubstituted monocyclic rings, or
[2522] They bond together to form substituted or unsubstituted fused rings, or
[2523] They do not bond with each other.
[2524] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 421 ~R 427 and R 431 ~R 438 Each independently
[2525] hydrogen atom,
[2526] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2527] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2528] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2529] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2530] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2531] -O-(R 904 The groups shown in the figure,
[2532] -S-(R 905 The groups shown in the figure,
[2533] -N(R 906 (R) 907 The groups shown in the figure,
[2534] Halogen atoms,
[2535] cyano,
[2536] Nitro,
[2537] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2538] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2539] 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).
[2540]
Chemical Formula 154
[2541]
[2542]
Chemical Formula 155
[2543]
[2544] [Chemical Formula 156]
[2545]
[2546] (In the above general formulas (41-3), (41-4), and (41-5),
[2547] Ring A1 is defined in the same way as in general formula (4) above.
[2548] R 421 ~R 427 Each independently relates to R in the above general formula (4-1) 421 ~R 427 Same meaning
[2549] R 440 ~R 448 Each independently relates to R in the above general formula (42) 401 ~R 411 The meaning is the same.
[2550] In one embodiment, the aromatic hydrocarbon ring of the above general formula (41-5) with 6 to 50 carbon atoms, either substituted or unsubstituted for the A1 ring, is...
[2551] Substituted or unsubstituted naphthalene ring or
[2552] Substituted or unsubstituted fluorene ring.
[2553] In one embodiment, the heterocycle of the above general formula (41-5), which has 5 to 50 cyclic atoms and is either substituted or unsubstituted for the A1 ring, is...
[2554] Substituted or unsubstituted dibenzofuran rings,
[2555] Substituted or unsubstituted carbazole ring or
[2556] Substituted or unsubstituted dibenzothiophene ring.
[2557] 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 the compounds represented by the following general formulas (461) to (467).
[2558] [Chemical Formula 157]
[2559]
[2560] [Chemical Formula 158]
[2561]
[2562] [Chemical Formula 159]
[2563]
[2564] [Chemical Formula 160]
[2565]
[2566]
Chemical Formula 161
[2567]
[2568] (In the above general formulas (461), (462), (463), (464), (465), (466), and (467),
[2569] R 421 ~R 427 Each independently relates to R in the above general formula (4-1) 421 ~R 427 Same meaning
[2570] R 431 ~R 438 Each independently relates to R in the above general formula (4-2) 431 ~R 438 Same meaning
[2571] R 440 ~R 448 and R 451 ~R 454 Each independently relates to R in the above general formula (42) 401 ~R 411 Same meaning
[2572] X4 represents an oxygen atom, NR 801 or C(R) 802 (R) 803 ),
[2573] R 801 R 802 and R 803 Each independently
[2574] hydrogen atom,
[2575] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2576] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2577] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2578] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2579] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[2580] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[2581] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[2582] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.
[2583] In R 803 In the case of multiple Rs, multiple Rs 803 (They may be the same or different.)
[2584] In one embodiment, for the compound represented by the above general formula (42), R 401 ~R 411 The compounds in this embodiment are described in detail as compounds represented by the following general formula (45), in which two or more adjacent groups are bonded to each other to form substituted or unsubstituted monocyclic rings or substituted or unsubstituted fused rings.
[2585] (The compound represented by general formula (45))
[2586] The compounds represented by general formula (45) will be described.
[2587]
Chemical Formula 162
[2588]
[2589] (In the above general formula (45),
[2590] Choose freely R 461 With R 462 The group formed, R 462 With R 463 The group formed, R 464 With R 465 The group formed, R 465 With R 466 The group formed, R 466 With R 467 The group formed, R 468 With R 469 The group formed, R 469 With R 470 The groups formed, and R 470 With R471 Within a larger group, two or more groups are bonded together to form substituted or unsubstituted monocyclic rings or substituted or unsubstituted fused rings.
[2591] in,
[2592] R 461 With R 462 The groups formed and R 462 With R 463 The groups do not simultaneously form a ring;
[2593] R 464 With R 465 The groups formed and R 465 With R 466 The groups do not simultaneously form a ring;
[2594] R 465 With R 466 The groups formed and R 466 With R 467 The groups do not simultaneously form a ring;
[2595] R 468 With R 469 The groups formed and R 469 With R 470 The groups do not simultaneously form a ring; and
[2596] R 469 With R 470 The groups formed and R 470 With R 471 The groups formed do not simultaneously form a ring.
[2597] R 461 ~R 471 Two or more rings are formed that are identical or different from each other.
[2598] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 461 ~R 471 Each independently
[2599] hydrogen atom,
[2600] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2601] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2602] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2603] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2604] -Si(R 901(R) 902 (R) 903 The groups shown in the figure,
[2605] -O-(R 904 The groups shown in the figure,
[2606] -S-(R 905 The group shown is -N(R) 906 (R) 907 The groups shown in the figure,
[2607] Halogen atoms,
[2608] cyano,
[2609] Nitro,
[2610] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2611] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2612] In the above general formula (45), R n With R n+1 (n represents an integer selected from 461, 462, 464-466 and 468-470) mutually bonded with R n and R n+1 The two bonded cyclic carbon atoms together form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring. The ring is preferably composed of atoms selected from carbon, oxygen, sulfur and nitrogen, and the number of atoms in the ring is preferably 3 to 7, more preferably 5 or 6.
[2613] The compound represented by the above general formula (45) may have, for example, two, three, or four ring structures. Two or more ring structures may each reside on the same benzene ring in the parent skeleton of the above general formula (45), or they may reside on different benzene rings. For example, in the case of three ring structures, one ring structure may reside on each of the three benzene rings in the above general formula (45).
[2614] Examples of the ring structures in the compounds represented by the general formula (45) above include those represented by the general formulas (451) to (460).
[2615] [Chemical Formula 163]
[2616]
[2617] (In the above general formulas (451) to (457),
[2618] *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14 represent R respectively. n and R n+1 The two cyclic carbon atoms bonded above,
[2619] R n The bonded cyclic carbon atoms can be any one of the two cyclic 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.
[2620] X 45 For C(R) 4512 (R) 4513 ), NR 4514 oxygen or sulfur atoms
[2621] R 4501 ~R 4506 and R 4512 ~R 4513 One or more of the groups consisting of two or more adjacent elements.
[2622] They bond together to form substituted or unsubstituted monocyclic rings, or
[2623] They bond together to form substituted or unsubstituted fused rings, or
[2624] They do not bond with each other.
[2625] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 4501 ~R 4514 Each independently relates to R in the above general formula (45) 461 ~R 471 The meaning is the same.
[2626] [Chemical Formula 164]
[2627]
[2628] (In the above general formulas (458) to (460),
[2629] *1 and *2, and *3 and *4 respectively represent R n and R n+1 The two cyclic carbon atoms bonded above,
[2630] R n The bonded cyclic carbon atoms can be any one of the two cyclic carbon atoms represented by *1 and *2 or *3 and *4.
[2631] X 45 For C(R) 4512 (R)4513 ), NR 4514 oxygen or sulfur atoms
[2632] R 4512 ~R 4513 and R 4515 ~R 4525 One or more of the groups consisting of two or more adjacent elements.
[2633] They bond together to form substituted or unsubstituted monocyclic rings, or
[2634] They bond together to form substituted or unsubstituted fused rings, or
[2635] They do not bond with each other.
[2636] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 4512 ~R 4513 R 4515 ~R 4521 and R 4522 ~R 4525 and R 4514 Each independently relates to R in the above general formula (45) 461 ~R 471 The meaning is the same.
[2637] In the above general formula (45), R is preferred. 462 R 464 R 465 R 470 and R 471 At least one of them (preferably R) 462 R 465 and R 470 At least one of them, further preferred R 462 () are groups that do not form ring structures.
[2638] (i) In the above general formula (45), R n With R n+1 When the formed ring structure has substituents, the substituents,
[2639] (ii) R in the above general formula (45) that does not form a ring structure 461 ~R 471 as well as
[2640] (iii) R in equations (451) to (460) 4501 ~R 4514 R 4515 ~R 4525 Each is preferred to be independent of the other.
[2641] hydrogen atom,
[2642] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2643] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2644] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2645] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2646] -N(R 906 (R) 907 The groups shown in the figure,
[2647] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[2648] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[2649] Any group in the group consisting of the groups represented by the following general formulas (461) to (464).
[2650] [Chemical Formula 165]
[2651]
[2652] (In the above general formulas (461) to (464),
[2653] R d Each independently
[2654] hydrogen atom,
[2655] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2656] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2657] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2658] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2659] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2660] -O-(R 904 The groups shown in the figure,
[2661] -S-(R 905 The groups shown in the figure,
[2662] -N(R 906 (R) 907 The groups shown in the figure,
[2663] Halogen atoms,
[2664] cyano,
[2665] Nitro,
[2666] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2667] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2668] X 46 For C(R) 801 (R) 802 ), NR 803 oxygen or sulfur atoms
[2669] R 801 R 802 and R 803 Each independently
[2670] hydrogen atom,
[2671] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2672] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2673] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2674] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2675] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[2676] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[2677] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[2678] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.
[2679] In R 803 In the case of multiple Rs, multiple Rs 803 They are the same or different.
[2680] p1 is 5.
[2681] p2 is 4.
[2682] p3 is 3.
[2683] p4 is 7.
[2684] In the above general formulas (461) to (464), each * independently represents a bonding position with the ring structure.
[2685] In the third and fourth compounds, R 901 ~R 907 Same as the definition described above.
[2686] In one embodiment, the compound represented by the above general formula (45) is represented by any one of the following general formulas (45-1) to (45-6).
[2687]
Chemical Formula 166
[2688]
[2689] [Chemical Formula 167]
[2690]
[2691] (In the above general formulas (45-1) to (45-6),
[2692] Each of the rings d to i is independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring.
[2693] R 461 ~R 471 Each independently relates to R in the above general formula (45) 461 ~R 471 The meaning is the same.
[2694] In one embodiment, the compound represented by the above general formula (45) is represented by any one of the following general formulas (45-7) to (45-12).
[2695] [Chemical Formula 168]
[2696]
[2697] [Chemical Formula 169]
[2698]
[2699] (In the above general formulas (45-7) to (45-12),
[2700] Rings d to f, k, and j are each independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring.
[2701] R 461 ~R 471 Each independently relates to R in the above general formula (45) 461 ~R 471The meaning is the same.
[2702] In one embodiment, the compound represented by the above general formula (45) is represented by any one of the following general formulas (45-13) to (45-21).
[2703] [Chemical Formula 170]
[2704]
[2705]
Chemical Formula 171
[2706]
[2707] [Chemical Formula 172]
[2708]
[2709] (In the above general formulas (45-13) to (45-21),
[2710] Each of the rings d to k is independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring.
[2711] R 461 ~R 471 Each independently relates to R in the above general formula (45) 461 ~R 471 The meaning is the same.
[2712] Substituents that further have substituents, such as those found in the above-mentioned ring g or ring h, can be exemplified by...
[2713] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2714] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[2715] The groups represented by the above general formula (461),
[2716] The groups represented by the above general formula (463) or
[2717] The group represented by the above general formula (464).
[2718] In one embodiment, the compound represented by the above general formula (45) is represented by any one of the following general formulas (45-22) to (45-25).
[2719]
Chemical Formula 173
[2720]
[2721] (In the above general formulas (45-22) to (45-25),
[2722] X 46 and X 47 Each independently is C(R) 801 (R) 802 ), NR 803 oxygen or sulfur atoms
[2723] R 461 ~R 471 and R 481 ~R 488 Each independently relates to R in the above general formula (45) 461 ~R 471 They have the same meaning.
[2724] R 801 R 802 and R 803 Each independently
[2725] hydrogen atom,
[2726] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2727] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2728] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2729] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2730] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[2731] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[2732] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[2733] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.
[2734] In R 803 In the case of multiple Rs, multiple Rs 803 (They may be the same or different.)
[2735] In one embodiment, the compound represented by the above general formula (45) is represented by the following general formulas (45-26).
[2736] [Chemical Formula 174]
[2737]
[2738] (In the above general formula (45-26),
[2739] X 46 For C(R) 801 (R) 802 ), NR 803 oxygen or sulfur atoms
[2740] R 463 R 464 R 467 R 468 R 471 and R 481 ~R 492 Each independently relates to R in the above general formula (45) 461 ~R 471 They have the same meaning.
[2741] R 801 R 802 and R 803 Each independently
[2742] hydrogen atom,
[2743] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2744] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2745] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2746] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2747] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[2748] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[2749] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[2750] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.
[2751] In R 803 In the case of multiple Rs, multiple Rs 803 (They may be the same or different.)
[2752] As a compound represented by the above general formula (4), the following compounds can be cited as specific examples. In the following specific examples, Ph represents a phenyl group and D represents a deuterium atom.
[2753] [Chemical Formula 175]
[2754]
[2755] [Chemical Formula 176]
[2756]
[2757] [Chemical Formula 177]
[2758]
[2759] [Chemical Formula 178]
[2760]
[2761] [Chemical Formula 179]
[2762]
[2763] [Chemical Formula 180]
[2764]
[2765]
Chemical Formula 181
[2766]
[2767]
Chemical Formula 182
[2768]
[2769] [Chemical Formula 183]
[2770]
[2771] [Chemical Formula 184]
[2772]
[2773] (The compound represented by general formula (5))
[2774] The compounds represented by general formula (5) will be described. The compounds represented by general formula (5) are the compounds corresponding to the compounds represented by general formula (41-3) above.
[2775] [Chemical Formula 185]
[2776]
[2777] (In the above general formula (5),
[2778] R 501 ~R507 and R 511 ~R 517 One or more of the groups consisting of two or more adjacent elements.
[2779] They bond together to form substituted or unsubstituted monocyclic rings, or
[2780] They bond together to form substituted or unsubstituted fused rings, or
[2781] They do not bond with each other.
[2782] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 501 ~R 507 and R 511 ~R 517 Each independently
[2783] hydrogen atom,
[2784] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2785] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2786] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2787] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2788] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2789] -O-(R 904 The groups shown in the figure,
[2790] -S-(R 905 The groups shown in the figure,
[2791] -N(R 906 (R) 907 The groups shown in the figure,
[2792] Halogen atoms,
[2793] cyano,
[2794] Nitro,
[2795] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2796] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[2797] R 521 and R 522 Each independently
[2798] hydrogen atom,
[2799] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2800] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2801] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2802] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2803] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2804] -O-(R 904 The groups shown in the figure,
[2805] -S-(R 905 The groups shown in the figure,
[2806] -N(R 906 (R) 907 The groups shown in the figure,
[2807] Halogen atoms,
[2808] cyano,
[2809] Nitro,
[2810] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2811] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2812] “R 501 ~R 507 and R 511 ~R 517 "One of the groups consisting of two or more adjacent elements" is, for example, R. 501 With R 502 The group formed, R 502 With R 503 The group formed, R 503 With R 504 The group formed, R 505 With R 506 The group formed, R 506 With R 507 The group formed, R 501 With R 502 With R 503 The groups and combinations formed by them.
[2813] In one implementation, R 501 ~R 507 and R 511 ~R 517 At least one, preferably two, of them are -N(R) 906 (R) 907 The group shown is ).
[2814] In one implementation, R 501 ~R 507 and R 511 ~R 517 Each independently
[2815] hydrogen atom,
[2816] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2817] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[2818] In one embodiment, the compound represented by the above general formula (5) is the compound represented by the following general formula (52).
[2819] [Chemical Formula 186]
[2820]
[2821] (In the above general formula (52),
[2822] R 531 ~R 534 and R 541 ~R 544 One or more of the groups consisting of two or more adjacent elements.
[2823] They bond together to form substituted or unsubstituted monocyclic rings, or
[2824] They bond together to form substituted or unsubstituted fused rings, or
[2825] They do not bond with each other.
[2826] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 531 ~R 534 R 541 ~R 544 and R 551 and R 552 Each independently
[2827] hydrogen atom,
[2828] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2829] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2830] R 561 ~R 564 Each independently
[2831] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2832] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2833] In one embodiment, the compound represented by the above general formula (5) is the compound represented by the following general formula (53).
[2834] [Chemical Formula 187]
[2835]
[2836] (In the above general formula (53), R) 551 R 552 and R 561 ~R 564 Each independently relates to R in the above general formula (52) 551 R 552 and R 561 ~R 564 The meaning is the same.
[2837] In one implementation, R in the above general formulas (52) and (53) 561 ~R 564 Each is independently a substituted or unsubstituted aryl group (preferably phenyl) with 6 to 50 carbon atoms in a cyclic structure.
[2838] In one implementation, R in the above general formula (5) 521 and R 522 R in the above general formulas (52) and (53) 551 and R 552 It is a hydrogen atom.
[2839] In one embodiment, the substituents expressed as "substituted or unsubstituted" in the above general formulas (5), (52), and (53) are...
[2840] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2841] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2842] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2843] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2844] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2845] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[2846] As a compound represented by the above general formula (5), the following compounds can be cited as specific examples.
[2847]
Chemical Formula 188
[2848]
[2849] [Chemical Formula 189]
[2850]
[2851] [Chemical Formula 190]
[2852]
[2853]
Chemical Formula 191
[2854]
[2855] [Chemical Formula 192]
[2856]
[2857] [Chemical Formula 193]
[2858]
[2859] [Chemical Formula 194]
[2860]
[2861] [Chemical Formula 195]
[2862]
[2863] [Chemical Formula 196]
[2864]
[2865] [Chemical Formula 197]
[2866]
[2867] [Chemical Formula 198]
[2868]
[2869]
Chemical Formula 199
[2870]
[2871] [Chemical Formula 200]
[2872]
[2873]
Chemical Formula 201
[2874]
[2875]
Chemical Formula 202
[2876]
[2877]
Chemical Formula 203
[2878]
[2879] (The compound represented by general formula (6))
[2880] The compounds represented by general formula (6) will be described.
[2881]
Chemical Formula 204
[2882]
[2883] (In the above general formula (6),)
[2884] Rings a, b, and c are each independently...
[2885] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or
[2886] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2887] R 601 and R 602 Each ring independently bonds to the aforementioned a-ring, b-ring, or c-ring to form a substituted or unsubstituted heterocycle, or not to form a substituted or unsubstituted heterocycle.
[2888] R does not form the aforementioned substituted or unsubstituted heterocycles 601 and R 602 Each independently
[2889] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2890] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2891] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2892] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2893] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2894] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2895] Rings a, b, and c are rings fused with the central fused 2-ring structure of the above general formula (6) consisting of boron atoms and two nitrogen atoms (substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 cyclic carbon atoms, or substituted or unsubstituted heterocycles with 5 to 50 cyclic atoms).
[2896] The "aromatic hydrocarbon rings" of rings a, b, and c have the same structure as compounds formed by introducing hydrogen atoms into the aforementioned "aryl" group.
[2897] The "aromatic hydrocarbon ring" of ring a contains three carbon atoms on the fused 2-ring structure in the center of the above general formula (6) as cyclic atoms.
[2898] The "aromatic hydrocarbon rings" of rings b and c contain two carbon atoms on the fused 2-ring structure in the center of the above general formula (6) as cyclic atoms.
[2899] As a specific example of "a cyclic aromatic hydrocarbon ring with 6 to 50 carbon atoms, whether substituted or unsubstituted", compounds formed by introducing hydrogen atoms into the "aryl" group described in Specific Example Group G1 can be cited.
[2900] The "heterocyclic" rings a, b, and c have the same structure as compounds formed by introducing hydrogen atoms into the aforementioned "heterocyclic groups".
[2901] The "heterocyclic ring" of ring a includes three carbon atoms in the fused 2-ring structure at the center of the above general formula (6) as cyclic atoms. The "heterocyclic rings" of rings b and c include two carbon atoms in the fused 2-ring structure at the center of the above general formula (6) as cyclic atoms. As a specific example of "heterocyclic rings with 5 to 50 substituted or unsubstituted cyclic atoms", compounds formed by introducing hydrogen atoms into the "heterocyclic group" described in specific example group G2 can be cited.
[2902] R 601 and R 602 Each ring can independently bond with ring a, ring b, or ring c to form substituted or unsubstituted heterocycles. In this case, the heterocycle contains the nitrogen atom in the fused 2-ring structure at the center of the general formula (6). The heterocycle may also contain heteroatoms other than the nitrogen atom. R 601 and R 602 Specifically, bonding with ring a, ring b, or ring c refers to the bonding between atoms constituting ring a, ring b, or ring c and atoms constituting ring R. 601 and R 602 The atoms are bonded together. For example, it could also be R. 601fused with α ring to form R 601 A nitrogen-containing heterocycle in which two rings (or three or more rings) are fused with the a ring. Specific examples of such nitrogen-containing heterocycles include compounds corresponding to the heterocyclic groups in Specific Example Group G2 that contain nitrogen and are fused with two or more rings.
[2903] R 601 Cases involving b-ring bonding, R 602 The case of α-ring bonding and R 602 The situation regarding bonding with the c-ring is the same as described above.
[2904] In one embodiment, ring a, ring b, and ring c in the above general formula (6) are each independently a substituted or unsubstituted aromatic hydrocarbon ring with 6 to 50 carbon atoms.
[2905] In one embodiment, ring a, ring b, and ring c in the above general formula (6) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.
[2906] In one implementation, R in the above general formula (6) 601 and R 602 Each independently
[2907] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2908] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2909] Preferably, it is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.
[2910] In one embodiment, the compound represented by the above general formula (6) is the compound represented by the following general formula (62).
[2911]
Chemical Formula 205
[2912]
[2913] (In the above general formula (62),
[2914] R 601A With selection from R 611 and R 621 One or more of them are bonded together to form a substituted or unsubstituted heterocycle, or they do not form a substituted or unsubstituted heterocycle.
[2915] R 602A With selection from R 613 and R 614 One or more of them are bonded together to form a substituted or unsubstituted heterocycle, or they do not form a substituted or unsubstituted heterocycle.
[2916] R does not form the aforementioned substituted or unsubstituted heterocycles 601A and R 602A Each independently
[2917] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2918] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2919] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2920] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2921] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2922] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2923] R 611 ~R 621 One or more of the groups consisting of two or more adjacent elements.
[2924] They bond together to form substituted or unsubstituted monocyclic rings, or
[2925] They bond together to form substituted or unsubstituted fused rings, or
[2926] They do not bond with each other.
[2927] R does not form the aforementioned substituted or unsubstituted heterocycles, does not form the aforementioned monocyclic rings, and does not form the aforementioned fused rings. 611 ~R 621 Each independently
[2928] hydrogen atom,
[2929] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2930] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2931] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2932] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2933] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2934] -O-(R 904 The groups shown in the figure,
[2935] -S-(R 905 The groups shown in the figure,
[2936] -N(R 906 (R) 907 The groups shown in the figure,
[2937] Halogen atoms,
[2938] cyano,
[2939] Nitro,
[2940] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2941] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2942] R in the above general formula (62) 601A and R 602A R, respectively, is the same as the general formula (6) above. 601 and R 602 The corresponding functional group.
[2943] For example, R 601A With R 611 These are nitrogen-containing heterocycles that are bonded together to form a fused two-ring (or three-ring or more) fused ring, comprising the rings containing the rings and a benzene ring corresponding to the α-ring. Specific examples of such nitrogen-containing heterocycles include compounds corresponding to the nitrogen-containing fused heterocyclic groups in Specific Example Group G2. R 601A With R 621 Bonding situation, R 602A With R 613 Bonding conditions and R 602A With R 614 The bonding situation is the same as above.
[2944] R 611 ~R 621 One or more of the two or more adjacent groups can
[2945] They bond together to form substituted or unsubstituted monocyclic rings, or
[2946] They bond together to form substituted or unsubstituted fused rings.
[2947] For example, R 611 With R 612 The bonds can be combined to form structures consisting of six-membered rings such as benzene rings, indole rings, pyrrole rings, benzofuran rings, or benzothiophene rings. The resulting fused rings can be naphthalene rings, carbazole rings, indole rings, dibenzofuran rings, or dibenzothiophene rings.
[2948] In one implementation, R does not participate in forming the ring. 611 ~R 621Each independently
[2949] hydrogen atom,
[2950] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2951] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2952] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[2953] In one implementation, R does not participate in forming the ring. 611 ~R 621 Each independently
[2954] hydrogen atom,
[2955] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2956] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[2957] In one implementation, R does not participate in forming the ring. 611 ~R 621 Each independently
[2958] hydrogen atom or
[2959] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted.
[2960] In one implementation, R does not participate in forming the ring. 611 ~R 621 Each independently
[2961] hydrogen atom or
[2962] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[2963] R 611 ~R 621 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[2964] In one embodiment, the compound represented by the above general formula (62) is the compound represented by the following general formula (63).
[2965]
Chemical Formula 206
[2966]
[2967] (In the above general formula (63),
[2968] R 631 With R 646Bonding to form substituted or unsubstituted heterocycles, or not forming substituted or unsubstituted heterocycles.
[2969] R 633 With R 647 Bonding to form substituted or unsubstituted heterocycles, or not forming substituted or unsubstituted heterocycles.
[2970] R 634 With R 651 Bonding to form substituted or unsubstituted heterocycles, or not forming substituted or unsubstituted heterocycles.
[2971] R 641 With R 642 Bonding to form substituted or unsubstituted heterocycles, or not forming substituted or unsubstituted heterocycles.
[2972] R 631 ~R 651 One or more of the groups consisting of two or more adjacent elements.
[2973] They bond together to form substituted or unsubstituted monocyclic rings, or
[2974] They bond together to form substituted or unsubstituted fused rings, or
[2975] They do not bond with each other.
[2976] R does not form the aforementioned substituted or unsubstituted heterocycles, does not form the aforementioned monocyclic rings, and does not form the aforementioned fused rings. 631 ~R 651 Each independently
[2977] hydrogen atom,
[2978] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2979] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2980] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2981] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2982] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2983] -O-(R 904 The groups shown in the figure,
[2984] -S-(R 905 The groups shown in the figure,
[2985] -N(R906 (R) 907 The groups shown in the figure,
[2986] Halogen atoms,
[2987] cyano,
[2988] Nitro,
[2989] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2990] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2991] R 631 Can be used with R 646 Bonding forms substituted or unsubstituted heterocycles. For example, R can be... 631 With R 646 Bonding to form fused R 646 The bonded benzene ring, or a nitrogen-containing heterocycle consisting of three or more rings fused together with a nitrogen-containing ring and a benzene ring corresponding to the a ring. Specific examples of such nitrogen-containing heterocycles include compounds corresponding to the nitrogen-containing heterocyclic groups fused together in Specific Example Group G2. R 633 With R 647 Bonding situation, R 634 With R 651 Bonding conditions and R 641 With R 642 The bonding situation is the same as above.
[2992] In one implementation, R does not participate in forming the ring. 631 ~R 651 Each independently
[2993] hydrogen atom,
[2994] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2995] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2996] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[2997] In one implementation, R does not participate in forming the ring. 631 ~R 651 Each independently
[2998] hydrogen atom,
[2999] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[3000] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[3001] In one implementation, R does not participate in forming the ring. 631 ~R 651 Each independently
[3002] hydrogen atom or
[3003] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted.
[3004] In one implementation, R does not participate in forming the ring. 631 ~R 651 Each independently
[3005] hydrogen atom or
[3006] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[3007] R 631 ~R 651 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[3008] In one embodiment, the compound represented by the above general formula (63) is the compound represented by the following general formula (63A).
[3009] [Chemical Formula 207]
[3010]
[3011] (In the above general formula (63A),
[3012] R 661 for
[3013] hydrogen atom,
[3014] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[3015] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[3016] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[3017] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or
[3018] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[3019] R 662 ~R 665 Each independently
[3020] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[3021] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[3022] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[3023] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or
[3024] (Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic structure.)
[3025] In one implementation, R 661 ~R 665 Each independently
[3026] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[3027] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.
[3028] In one implementation, R 661 ~R 665 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[3029] In one embodiment, the compound represented by the above general formula (63) is the compound represented by the following general formula (63B).
[3030] [Chemical Formula 208]
[3031]
[3032] (In the above general formula (63B),
[3033] R 671 and R 672 Each independently
[3034] hydrogen atom,
[3035] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[3036] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[3037] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[3038] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[3039] -N(R 906 (R) 907 The group or shown in the figure
[3040] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[3041] R 673 ~R 675 Each independently
[3042] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[3043] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[3044] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[3045] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[3046] -N(R 906 (R) 907 The group or shown in the figure
[3047] (Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic structure.)
[3048] In one embodiment, the compound represented by the above general formula (63) is the compound represented by the following general formula (63B').
[3049]
Chemical Formula 209
[3050]
[3051] (In the above general formula (63B'), R) 672 ~R 675 Each independently relates to R in the above general formula (63B) 672 ~R 675 The meaning is the same.
[3052] In one implementation, R 671 ~R 675 At least one of them is
[3053] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[3054] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[3055] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[3056] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[3057] -N(R 906 (R) 907 The group or shown in the figure
[3058] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.
[3059] In one implementation method
[3060] R 672 for
[3061] hydrogen atom,
[3062] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[3063] -N(R 906 (R) 907 The group or shown in the figure
[3064] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[3065] R 671 and R 673 ~R 675 Each independently
[3066] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[3067] -N(R 906 (R) 907 The group or shown in the figure
[3068] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.
[3069] In one embodiment, the compound represented by the above general formula (63) is the compound represented by the following general formula (63C).
[3070]
Chemical Formula 210
[3071]
[3072] (In the above general formula (63C),
[3073] R 681 and R 682 Each independently
[3074] hydrogen atom,
[3075] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[3076] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[3077] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[3078] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or
[3079] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.
[3080] R 683 ~R 686 Each independently
[3081] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[3082] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[3083] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[3084] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or
[3085] (Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic structure.)
[3086] In one embodiment, the compound represented by the above general formula (63) is the compound represented by the following general formula (63C').
[3087]
Chemical Formula 211
[3088]
[3089] (In the above general formula (63C'), R) 683 ~R 686 Each independently relates to R in the above general formula (63C). 683 ~R 686 The meaning is the same.
[3090] In one implementation, R 681 ~R 686 Each independently
[3091] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[3092] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.
[3093] In one implementation, R 681 ~R 686 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure.
[3094] For the compound shown in the general formula (6) above, the a ring, b ring and c ring can first be connected by a linking group (containing NR). 601 Groups and containing NR 602 The intermediate is produced by bonding the boron rings (a, b, and c) with a linking group (a group containing boron atoms). The final product is then produced by bonding the a, b, and c rings together with a linking group (a group containing boron atoms). Amination reactions such as the Buchwald-Hartwig reaction can be used in the first reaction. The tandem hetero Friedel-Crafts reaction can be used in the second reaction.
[3095] Although specific examples of compounds represented by the above general formula (6) are described below, these are merely examples, and the compounds represented by the above general formula (6) are not limited to the specific examples described below.
[3096]
Chemical Formula 212
[3097]
[3098]
Chemical Formula 213
[3099]
[3100]
Chemical Formula 214
[3101]
[3102]
Chemical Formula 215
[3103]
[3104]
Chemical Formula 216
[3105]
[3106]
Chemical Formula 217
[3107]
[3108]
Chemical Formula 218
[3109]
[3110]
Chemical Formula 219
[3111]
[3112]
Chemical Formula 220
[3113]
[3114]
Chemical Formula 221
[3115]
[3116]
Chemical Formula 222
[3117]
[3118]
Chemical Formula 223
[3119]
[3120] (The compound represented by general formula (7))
[3121] The compounds represented by general formula (7) will be described.
[3122] [Chemical Formula 224]
[3123]
[3124] [Chemical Formula 225]
[3125]
[3126] (In the above general formula (7),
[3127] The r-ring is a ring shown in the above general formula (72) or general formula (73) that is fused at any position of adjacent rings.
[3128] The q-ring and s-ring are each independently rings fused at any position of adjacent rings as shown in the above general formula (74).
[3129] The p-ring and t-ring are each independently structures shown in the above general formula (75) or general formula (76) that are fused at any position of adjacent rings.
[3130] X7 represents an oxygen atom, a sulfur atom, or NR. 702 .
[3131] In R 701 In the case of multiple occurrences, multiple adjacent R 701
[3132] They bond together to form substituted or unsubstituted monocyclic rings, or
[3133] They bond together to form substituted or unsubstituted fused rings, or
[3134] They do not bond with each other.
[3135] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 701 and R 702 Each independently
[3136] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[3137] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[3138] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[3139] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[3140] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[3141] -O-(R 904 The groups shown in the figure,
[3142] -S-(R 905 The groups shown in the figure,
[3143] -N(R 906 (R) 907 The groups shown in the figure,
[3144] Halogen atoms,
[3145] cyano,
[3146] Nitro,
[3147] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[3148] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[3149] Ar 701 and Ar 702 Each independently
[3150] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[3151] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[3152] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[3153] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[3154] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[3155] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[3156] L 701 for
[3157] Substituted or unsubstituted alkylene groups having 1 to 50 carbon atoms
[3158] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[3159] Substituted or unsubstituted ynylene groups with 2 to 50 carbon atoms
[3160] Substituted or unsubstituted cycloalkylene groups with 3 to 50 carbon atoms
[3161] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[3162] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[3163] m1 is 0, 1, or 2.
[3164] m2 can be 0, 1, 2, 3, or 4.
[3165] m3 can be independently 0, 1, 2 or 3.
[3166] Each m4 is independently 0, 1, 2, 3, 4, or 5.
[3167] In R 701 In the case of multiple Rs, multiple Rs 701 They are the same or different.
[3168] When multiple X7s exist, these X7s may be identical or different from each other.
[3169] In R 702 In the case of multiple Rs, multiple Rs 702 They are the same or different.
[3170] In Ar 701 In the case of multiple instances, multiple Ar 701 They are the same or different.
[3171] In Ar 702 In the case of multiple instances, multiple Ar 702 They are the same or different.
[3172] In L 701 In the case of multiple Ls, multiple Ls 701 (They may be the same or different.)
[3173] In the above general formula (7), each of the p-ring, q-ring, r-ring, s-ring, and t-ring is fused with its adjacent ring by two carbon atoms. The position and direction of fusion are not limited, and fusion can occur at any position and in any direction.
[3174] In one embodiment, in the above general formula (72) or general formula (73) which is an r-ring, m1 = 0 or m2 = 0.
[3175] 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).
[3176]
Chemical Formula 226
[3177]
[3178] [Chemical Formula 227]
[3179]
[3180] [Chemical Formula 228]
[3181]
[3182] [Chemical Formula 229]
[3183]
[3184]
Chemical Formula 230
[3185]
[3186]
Chemical Formula 231
[3187]
[3188] (In the above general formulas (71-1) to (71-6), R) 701 X7, Ar 701 Ar 702 L 701 m1 and m3 are respectively related to R in the above general formula (7). 701 X7, Ar 701 Ar 702 L 701 (m1 and m3 have the same meaning.)
[3189] 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).
[3190]
Chemical Formula 232
[3191]
[3192]
Chemical Formula 233
[3193]
[3194]
Chemical Formula 234
[3195]
[3196] (In the above general formulas (71-11) to (71-13), R) 701 X7, Ar 701 Ar 702 L 701 m1, m3 and m4 are respectively related to R in the above general formula (7) 701 X7, Ar 701 Ar 702 L 701 m1, m3, and m4 have the same meaning.
[3197] 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).
[3198] [Chemical Formula 235]
[3199]
[3200]
Chemical Formula 236
[3201]
[3202] [Chemical Formula 237]
[3203]
[3204] [Chemical Formula 238]
[3205]
[3206] [Chemical Formula 239]
[3207]
[3208] (In the above general formulas (71-21) to (71-25), R) 701 X7, Ar 701 Ar 702 L 701 m1 and m4 are respectively related to R in the above general formula (7). 701 X7, Ar 701 Ar 702 L 701 (m1 and m4 have the same meaning.)
[3209] 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 (71-33).
[3210] [Chemical Formula 240]
[3211]
[3212]
Chemical Formula 241
[3213]
[3214]
Chemical Formula 242
[3215]
[3216] (In the above general formulas (71-31) to (71-33), R) 701 X7, Ar 701Ar 702 L 701 m2 to m4 are respectively related to R in the above general formula (7). 701 X7, Ar 701 Ar 702 L 701 (m2 to m4 have the same meaning.)
[3217] In one implementation, Ar 701 and Ar 702 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure.
[3218] In one implementation, Ar 701 and Ar 702 One of them is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic ring, Ar 701 and Ar 702 The other one is a heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[3219] As a compound represented by the above general formula (7), the following compounds can be cited as specific examples.
[3220] [Chemical Formula 243]
[3221]
[3222] [Chemical Formula 244]
[3223]
[3224] [Chemical Formula 245]
[3225]
[3226] [Chemical Formula 246]
[3227]
[3228] [Chemical Formula 247]
[3229]
[3230] [Chemical Formula 248]
[3231]
[3232] (The compound represented by general formula (8))
[3233] The compounds represented by general formula (8) will be described.
[3234] [Chemical Formula 249]
[3235]
[3236] (In the above general formula (8),
[3237] R 801 With R 802 R 802 With R 803 and R 803 With R 804 At least one group in the group is bonded to each other to form a divalent group as shown in the following general formula (82).
[3238] R 805 With R 806 R 806 With R 807 and R 807 With R 808 At least one group of the radicals bonds together to form a divalent group as shown in the general formula (83).
[3239] [Chemical Formula 250]
[3240]
[3241] (R that does not form the divalent group shown in the above general formula (82)) 801 ~R 804 and R 811 ~R 814 At least one of them is a monovalent group represented by the following general formula (84),
[3242] R that does not form the divalent group shown in the above general formula (83) 805 ~R 808 and R 821 ~R 824 At least one of them is a monovalent group represented by the following general formula (84),
[3243] X8 represents an oxygen atom, a sulfur atom, or NR. 809 ,
[3244] R that does not form the divalent groups shown in general formulas (82) and (83) above and is not the monovalent group shown in general formula (84) above. 801 ~R 808 R that is not a monovalent group as shown in the above general formula (84) 811 ~R 814 and R 821 ~R 824 and R 809 Each independently
[3245] hydrogen atom,
[3246] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[3247] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[3248] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[3249] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[3250] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[3251] -O-(R 904 The groups shown in the figure,
[3252] -S-(R 905 The groups shown in the figure,
[3253] -N(R 906 (R) 907 The groups shown in the figure,
[3254] Halogen atoms,
[3255] cyano,
[3256] Nitro,
[3257] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[3258] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[3259]
Chemical Formula 251
[3260]
[3261] (In the above general formula (84),
[3262] Ar 801 and Ar 802 Each independently
[3263] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[3264] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[3265] L 801 ~L 803 Each independently
[3266] single bond,
[3267] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms
[3268] Substituted or unsubstituted divalent heterocyclic groups with 5 to 30 cyclic atoms, or
[3269] A divalent linker is formed by bonding 2 to 4 groups from the group consisting of a substituted or unsubstituted aryl group with 6 to 30 carbon atoms and a substituted or unsubstituted divalent heterocyclic group with 5 to 30 carbon atoms.
[3270] In the above general formula (84), * indicates the bonding position with the ring structure shown in general formula (8), or the group shown in general formula (82) or general formula (83).
[3271] In the above general formula (8), the positions of the divalent groups shown in general formula (82) and general formula (83) are not particularly limited, and can be formed in R 801 ~R 808 The group can be formed at any of the possible positions.
[3272] 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).
[3273]
Chemical Formula 252
[3274]
[3275] [Chemical Formula 253]
[3276]
[3277] [Chemical Formula 254]
[3278]
[3279] (In the above general formulas (81-1) to (81-6),
[3280] X8 has the same meaning as X8 in the above general formula (8).
[3281] R 801 ~R 824 At least two of them are monovalent groups as shown in the above general formula (84).
[3282] R is not a monovalent group as shown in the above general formula (84) 801 ~R 824 Each independently
[3283] hydrogen atom,
[3284] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[3285] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[3286] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[3287] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[3288] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[3289] -O-(R 904 The groups shown in the figure,
[3290] -S-(R 905 The groups shown in the figure,
[3291] -N(R 906 (R) 907 The groups shown in the figure,
[3292] Halogen atoms,
[3293] cyano,
[3294] Nitro,
[3295] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[3296] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[3297] 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).
[3298] [Chemical Formula 255]
[3299]
[3300] [Chemical Formula 256]
[3301]
[3302] [Chemical Formula 257]
[3303]
[3304] [Chemical Formula 258]
[3305]
[3306] [Chemical Formula 259]
[3307]
[3308] [Chemical Formula 260]
[3309]
[3310] (In the above general formulas (81-7) to (81-18),
[3311] X8 has the same meaning as X8 in the above general formula (8).
[3312] * represents a single bond bonded to the monovalent group shown in the above general formula (84).
[3313] R 801 ~R 824 Each independently relates to the R group in the above general formulas (81-1) to (81-6) that is not the monovalent group shown in the above general formula (84). 801 ~R 824 The meaning is the same.
[3314] R that does not form the divalent groups shown in general formulas (82) and (83) above and is not the monovalent group shown in general formula (84) above. 801 ~R 808 And R groups that are not monovalent groups represented by the above general formula (84) 811 ~R 814 and R 821 ~R 824 Preferred to be independent
[3315] hydrogen atom,
[3316] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[3317] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[3318] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[3319] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[3320] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[3321] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[3322] The monovalent group represented by the above general formula (84) is preferably represented by the following general formula (85) or general formula (86).
[3323]
Chemical Formula 261
[3324]
[3325] (In the above general formula (85),
[3326] R 831~R 840 Each independently
[3327] hydrogen atom,
[3328] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[3329] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[3330] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[3331] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[3332] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[3333] -O-(R 904 The groups shown in the figure,
[3334] -S-(R 905 The groups shown in the figure,
[3335] -N(R 906 (R) 907 The groups shown in the figure,
[3336] Halogen atoms,
[3337] cyano,
[3338] Nitro,
[3339] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[3340] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[3341] The asterisk (*) in the above general formula (85) has the same meaning as the asterisk (*) in the above general formula (84).
[3342]
Chemical Formula 262
[3343]
[3344] (In the above general formula (86),
[3345] Ar 801 L 801 and L 803 Ar in the above general formula (84) 801 L 801 and L 803 Same meaning
[3346] HAr 801The structure is shown in the following general formula (87).
[3347] [Chemical Formula 263]
[3348]
[3349] (In the above general formula (87),
[3350] X 81 It consists of oxygen or sulfur atoms.
[3351] R 841 ~R 848 Any one of them is related to L 803 Bonded single bonds,
[3352] R is not a single bond 841 ~R 848 Each independently
[3353] hydrogen atom,
[3354] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[3355] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[3356] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[3357] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[3358] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[3359] -O-(R 904 The groups shown in the figure,
[3360] -S-(R 905 The groups shown in the figure,
[3361] -N(R 906 (R) 907 The groups shown in the figure,
[3362] Halogen atoms,
[3363] cyano,
[3364] Nitro,
[3365] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[3366] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[3367] As a compound represented by the above general formula (8), the compounds disclosed in International Publication No. 2014 / 104144 and, for example, the compounds shown below can be cited as specific examples.
[3368] [Chemical Formula 264]
[3369]
[3370] [Chemical Formula 265]
[3371]
[3372]
Chemical Formula 266
[3373]
[3374] [Chemical Formula 267]
[3375]
[3376] [Chemical Formula 268]
[3377]
[3378] [Chemical Formula 269]
[3379]
[3380] (The compound represented by general formula (9))
[3381] The compounds represented by general formula (9) will be described.
[3382] [Chemical Formula 270]
[3383]
[3384] (In the above general formula (9),
[3385] A 91 Ring and A 92 Each ring is independent of the others.
[3386] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or...
[3387] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.
[3388] Selected from A 91 Ring and A 92 One or more rings in the ring are bonded to the structure shown in the following general formula (92).
[3389]
Chemical Formula 271
[3390]
[3391] (In the above general formula (92),
[3392] A 93 Ring for
[3393] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or...
[3394] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.
[3395] 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,
[3396] R 91 and R 92
[3397] They bond together to form substituted or unsubstituted monocyclic rings, or
[3398] They bond together to form substituted or unsubstituted fused rings, or
[3399] They do not bond with each other.
[3400] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 91 and R 92 and R 93 ~R 99 Each independently
[3401] hydrogen atom,
[3402] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[3403] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[3404] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[3405] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[3406] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[3407] -O-(R 904 The groups shown in the figure,
[3408] -S-(R 905 The groups shown in the figure,
[3409] -N(R 906 (R) 907 The groups shown in the figure,
[3410] Halogen atoms,
[3411] cyano,
[3412] Nitro,
[3413] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[3414] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[3415] Selected from A 91 Ring and A 92 One or more rings in the ring are bonded to the structure shown in the above general formula (92). That is, in one embodiment, A 91 The cyclic carbon atom of the aforementioned aromatic hydrocarbon ring or the cyclic atom of the aforementioned heterocycle is bonded to the structure shown in the aforementioned general formula (92). Additionally, in one embodiment, A 92 The cyclic carbon atom of the above-mentioned aromatic hydrocarbon ring or the cyclic atom of the above-mentioned heterocycle is bonded to the structure shown in the above-mentioned general formula (92).
[3416] In one embodiment, the group represented by the following general formula (93) is bonded to A 91 Ring and A 92 One or both of them in the ring.
[3417]
Chemical Formula 272
[3418]
[3419] (In the above general formula (93),
[3420] Ar 91 and Ar 92 Each independently
[3421] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[3422] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[3423] L 91 ~L 93 Each independently
[3424] single bond,
[3425] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms
[3426] Substituted or unsubstituted divalent heterocyclic groups with 5 to 30 cyclic atoms, or
[3427] A divalent linking group is formed by bonding 2 to 4 groups from the group consisting of a substituted or unsubstituted aryl group with 6 to 30 carbon atoms and a substituted or unsubstituted divalent heterocyclic group with 5 to 30 carbon atoms.
[3428] In the above general formula (93), * indicates that it is related to A. 91 Ring and A 92 The bonding position of any ring within the ring.
[3429] In one implementation, besides A 91 Outside the ring, there is A. 92 The cyclic carbon atom of the aforementioned aromatic hydrocarbon ring or the cyclic atom of the aforementioned heterocycle is bonded to the structure shown in the aforementioned general formula (92). In this case, the structures shown in the aforementioned general formula (92) may be the same as or different from each other.
[3430] In one implementation, R 91 and R 92 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure.
[3431] In one implementation, R 91 and R 92 They bond together to form a fluorene structure.
[3432] In one implementation, ring A 91 And Ring A 92 Each is an aromatic hydrocarbon ring, either substituted or unsubstituted, having 6 to 50 carbon atoms, such as a substituted or unsubstituted benzene ring.
[3433] In one implementation, ring A 93 A cyclic aromatic hydrocarbon ring with 6 to 50 carbon atoms, either substituted or unsubstituted, such as a substituted or unsubstituted benzene ring.
[3434] In one implementation, X9 is an oxygen atom or a sulfur atom.
[3435] As a compound represented by the above general formula (9), the following compounds can be cited as specific examples.
[3436] [Chemical Formula 273]
[3437]
[3438] [Chemical Formula 274]
[3439]
[3440] [Chemical Formula 275]
[3441]
[3442] [Chemical Formula 276]
[3443]
[3444] (The compound represented by general formula (10))
[3445] The compounds represented by general formula (10) will be described.
[3446] [Chemical Formula 277]
[3447]
[3448] [Chemical Formula 278]
[3449]
[3450] (In the above general formula (10),
[3451] Ax1 ring is a ring as shown in the above general formula (10a) that is fused at any position of adjacent rings.
[3452] Ax2 ring is a ring as shown in the above general formula (10b) that is fused at any position between adjacent rings.
[3453] The two asterisks in the above general formula (10b) are bonded to any position of the Ax3 ring.
[3454] X A and X B Each independently is C(R) 1003 (R) 1004 ), Si(R) 1005 (R) 1006 ), oxygen atom or sulfur atom,
[3455] Ax3 ring is
[3456] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or
[3457] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.
[3458] Ar 1001 for
[3459] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[3460] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[3461] R1001 ~R 1006 Each independently
[3462] hydrogen atom,
[3463] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[3464] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[3465] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[3466] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[3467] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[3468] -O-(R 904 The groups shown in the figure,
[3469] -S-(R 905 The groups shown in the figure,
[3470] -N(R 906 (R) 907 The groups shown in the figure,
[3471] Halogen atoms,
[3472] cyano,
[3473] Nitro,
[3474] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[3475] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[3476] mx1 is 3, mx2 is 2.
[3477] Multiple R 1001 They are the same or different.
[3478] Multiple R 1002 They are the same or different.
[3479] ax is 0, 1, or 2.
[3480] When ax is 0 or 1, the structures within the parentheses shown in "3-ax" may be the same or different from each other.
[3481] When ax = 2, multiple Ar 1001 (They may be the same or different.)
[3482] In one implementation, Ar 1001 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.
[3483] In one embodiment, the Ax3 ring is a substituted or unsubstituted aromatic hydrocarbon ring with 6 to 50 carbon atoms, such as a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted anthracene ring.
[3484] In one implementation, R 1003 and R 1004 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[3485] In one implementation, ax is 1.
[3486] As a compound represented by the above general formula (10), the following compounds can be cited as specific examples.
[3487] [Chemical Formula 279]
[3488]
[3489] In one embodiment, the light-emitting layer contains, as at least one of the third and fourth compounds, a compound selected from...
[3490] The compounds represented by the above general formula (4),
[3491] The compounds represented by the above general formula (5),
[3492] The compounds represented by the above general formula (7),
[3493] The compounds represented by the above general formula (8),
[3494] The compounds represented by the above general formula (9) and
[3495] One or more compounds in the group consisting of compounds represented by the following general formula (63a).
[3496] [Chemical Formula 280]
[3497]
[3498] (In the above general formula (63a),
[3499] R 631 With R 646 They may bond to form substituted or unsubstituted heterocycles, or they may not form substitut...
Claims
1. An organic electroluminescent element having anode, 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. The first light-emitting layer contains a first compound having a group represented by the following general formula (11) and represented by the following general formula (1) as a first host material. The second light-emitting layer contains a second compound represented by the following general formula (2) as a second host material. The first light-emitting layer and the second light-emitting layer are directly connected. In the general formula (1), R 101 ~R 110 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms Substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, or The group represented by the general formula (11), in, R 101 ~R 110 One of them is a group represented by the general formula (11). L 101 For substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic structure, mx is 1 or 2 Ar 101 The fluorene group may be substituted or unsubstituted, or the benzo[a]fluorene group may be substituted or unsubstituted. Ar 101 When described as "substituted or unsubstituted", the substituent is an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms. As L 101 The substituted or unsubstituted aryl group with 6 to 50 carbon atoms is derived from substituted or unsubstituted phenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted meta-biphenyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted p-terphenyl-4-yl, substituted or unsubstituted p-terphenyl-3-yl, substituted or unsubstituted p-terphenyl-2-yl, substituted or unsubstituted m-terphenyl-4-yl, substituted or unsubstituted m-terphenyl-3-yl, substituted or unsubstituted m-terphenyl-2-yl, substituted or unsubstituted o-terphenyl-4-yl, substituted or unsubstituted The divalent group derived therefrom by removing one hydrogen atom from the aryl ring of o-terphenyl-3-yl, substituted or unsubstituted o-terphenyl-2-yl, substituted or unsubstituted anthraquinone, substituted or unsubstituted benzo[a]anthraquinone, substituted or unsubstituted phenanthranil, substituted or unsubstituted phenatenyl, substituted or unsubstituted benzo[a]anthraquinone, substituted or unsubstituted benzo[a]anthraquinone, substituted or unsubstituted benzo[a]anthraquinone, or 9,9-dimethylfluorenyl. In L 101 When there are more than two, more than two L 101 They are the same or different. In the general formula (11) This indicates the bonding position with the pyrene ring in the general formula (1). In the general formula (2), R 201 ~R 208 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. L 201 and L 202 Each independently single bond, Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 201 and Ar 202 Each independently Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the second compound represented by general formula (2), R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different. In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different. In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different. In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different. In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different. In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different. In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different. In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different. In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.
2. The organic electroluminescent element according to claim 1, wherein, At least one L 101 To remove a divalent group derived therefrom from a substituted or unsubstituted phenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted meta-biphenyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted p-terphenyl-4-yl, substituted or unsubstituted p-terphenyl-3-yl, substituted or unsubstituted p-terphenyl-2-yl, substituted or unsubstituted m-terphenyl-4-yl, substituted or unsubstituted m-terphenyl-3-yl, substituted or unsubstituted m-terphenyl-2-yl, substituted or unsubstituted o-terphenyl-4-yl, substituted or unsubstituted o-terphenyl-3-yl, substituted or unsubstituted o-terphenyl-2-yl, substituted or unsubstituted phenanthrene, or 9,9-dimethylfluorenyl.
3. The organic electroluminescent element according to claim 1 or 2, wherein, Ar 101 It can be a substituted or unsubstituted benzofluorene group.
4. The organic electroluminescent element according to claim 1 or 2, wherein, The group represented by general formula (11) is the group represented by the following general formula (111). In the general formula (111), X1 is CR 123 R 124 , L 111 and L 112 Each independently relates to L in the general formula (11) 101 Same meaning ma is 0 or 1. mb is 0 or 1, ma + mb is 0 or 1. Ar 101 Ar in the general formula (11) 101 Same meaning R 121 R 122 It is a hydrogen atom. R 123 and R 124 It is methyl. mc is 3. 3 Rs 121 They are the same or different. md is 3 3 Rs 122 They are the same or different.
5. The organic electroluminescent element according to claim 4, wherein, The group represented by the general formula (111) is represented by the following general formula (111b). In the general formula (111b), X1, L 111 L 112 ma, mb, Ar 101 R 121 R 122 R 123 R 124 and R 125 Each independently relates to X1 and L in the general formula (111). 111 L 112 ma, mb, Ar 101 R 121 R 122 R 123 R 124 and R 125 Same meaning Multiple R 121 They are the same or different. Multiple R 122 They are the same or different.
6. The organic electroluminescent element according to claim 4, wherein, ma is 0. mb is 0.
7. The organic electroluminescent element according to claim 1 or 2, wherein, Ar 101 The fluorene group can be substituted or unsubstituted.
8. The organic electroluminescent element according to claim 1 or 2, wherein, Ar 101 When expressed as "substituted or unsubstituted", the substituent is an alkyl group having 1 to 6 carbon atoms.
9. The organic electroluminescent element according to claim 1 or 2, wherein, R 101 ~R 110 L 101 The substituents in general formula (2) that are expressed as "substituted or unsubstituted" do not include substituted or unsubstituted pyrene groups.
10. The organic electroluminescent element according to claim 1 or 2, wherein, The first compound is a compound that has only one pyrene ring in its molecule.
11. The organic electroluminescent element according to claim 1 or 2, wherein, The organic electroluminescent element emits light with a main peak wavelength of 430 nm or higher and 480 nm or lower when the element is driven.
12. The organic electroluminescent element according to claim 1, wherein, The second luminescent layer also contains a fourth fluorescent compound.
13. The organic electroluminescent element according to claim 1, wherein, The second light-emitting layer also contains a fourth fluorescent compound. The fourth compound is a compound that exhibits luminescence with a main peak wavelength above 430 nm and below 480 nm.
14. The organic electroluminescent element according to claim 12 or 13, wherein, The content of the second compound in the second light-emitting layer is 80% by mass or more and 99% by mass or less.
15. The organic electroluminescent element according to claim 12 or 13, wherein, The content of the fourth compound in the second luminescent layer is more than 1% by mass and less than 10% by mass.
16. The organic electroluminescent element according to claim 12, wherein, The singlet state energy S1(H2) of the second compound and the singlet state energy S1(D4) of the fourth compound satisfy the following mathematical expression (Mathematical Expression 2). S1(H2)>S1(D4)…(Mathematical Formula 2).
17. The organic electroluminescent element according to claim 1, wherein, The first luminescent layer also contains a third compound with fluorescent properties.
18. The organic electroluminescent element according to claim 1, wherein, The first light-emitting layer also contains a third fluorescent compound. The third compound is a compound that exhibits luminescence with a main peak wavelength of 430 nm or higher and 480 nm or lower.
19. The organic electroluminescent element according to claim 17 or 18, wherein, The content of the first compound in the first light-emitting layer is 80% by mass or more and 99% by mass or less.
20. The organic electroluminescent element according to claim 17 or 18, wherein, The content of the third compound in the first luminescent layer is more than 1% by mass and less than 10% by mass.
21. The organic electroluminescent element according to claim 17, wherein, The singlet state energy S1(H1) of the first compound and the singlet state energy S1(D3) of the third compound satisfy the following mathematical expression (Mathematical Expression 1): S1(H1)>S1(D3)…(Mathematical Formula 1).
22. The organic electroluminescent element according to claim 13 or 18, wherein, The peak wavelength of the main peak of the compound is 10 times that of the compound prepared as the test target. -6 mol / L or higher and 10 -5 A toluene solution with a concentration of less than mol / L is added to a quartz cuvette, and the emission spectrum of the sample is measured at 300K. The peak wavelength of the emission spectrum in which the emission intensity reaches its maximum is the vertical axis of the emission spectrum, which represents the emission intensity and the horizontal axis represents the wavelength.
23. The organic electroluminescent element according to claim 16 or 21, wherein, 10 compounds prepared for determination of singlet energy S1 -5 mol / L or higher and 10 -4 A toluene solution with a concentration below mol / L was added to a quartz cuvette, and the absorption spectrum of the sample was measured at 300 K. A downward-sloping tangent was drawn on the longer wavelength side of the absorption spectrum. The wavelength value λedge at the intersection of this tangent and the horizontal axis was substituted into the conversion formula (F2) shown later to calculate the singlet energy S1. Conversion formula (F2): S1 = 1239.85 / λedge In this absorption spectrum, the vertical axis represents the absorption intensity, the horizontal axis represents the wavelength, the wavelength value λedge is in nm, and the unit of S1 is eV.
24. The organic electroluminescent element according to claim 12 or 17, wherein, The third compound or the fourth compound is each independently selected from... The compounds represented by the following general formula (3), The compounds represented by the following general formula (4), The compounds represented by the following general formula (5), The compounds represented by the following general formula (6), The compounds represented by the following general formula (7), The compounds represented by the following general formula (8), The compounds represented by the following general formula (9) and One or more compounds of the following general formula (10) In the general formula (3), R 301 ~R 310 One or more of the groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings, or They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R 301 ~R 310 At least one of them is a monovalent group represented by the following general formula (31), R that does not form the monocyclic ring, does not form the fused ring, and is not a monovalent group represented by the following general formula (31) 301 ~R 310 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the general formula (31), Ar 301 and Ar 302 Each independently Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. L 301 ~L 303 Each independently single bond, Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted. This indicates the bonding position in the pyrene ring in the general formula (3). In the general formula (4), Z can be independently represented by CRa or nitrogen atoms. Rings A1 and A2 are each independent of each other. Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted. When there are multiple Ra, one or more groups consisting of two or more adjacent Ra are selected. They bond together to form substituted or unsubstituted monocyclic rings, or They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. n21 and n22 are each independently 0, 1, 2, 3 or 4. When there are multiple Rb, one or more groups consisting of two or more adjacent Rb are considered. They bond together to form substituted or unsubstituted monocyclic rings, or They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. When there are multiple Rc, one or more groups are formed by two or more adjacent Rc. They bond together to form substituted or unsubstituted monocyclic rings, or They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. Ra, Rb, and Rc, which do not form the single ring and do not form the fused ring, are each independently [value missing]. Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the general formula (5), R 501 ~R 507 and R 511 ~R 517 One or more of the groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings, or They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R that does not form the single ring and does not form the fused ring 501 ~R 507 and R 511 ~R 517 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. R 521 and R 522 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the general formula (6), Rings a, b, and c are each independently... Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted. R 601 and R 602 Each ring independently bonds to ring a, ring b, or ring c to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R does not form the substituted or unsubstituted heterocycles. 601 and R 602 Each independently Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the general formula (7), The r-ring is a ring represented by the general formula (72) or general formula (73) that is fused at any position of adjacent rings. The q-ring and s-ring are each independently rings fused at any position of adjacent rings as shown in the general formula (74). The p-ring and t-ring are each independently structures shown in general formula (75) or general formula (76) that are fused at any position of adjacent rings. X7 represents an oxygen atom, a sulfur atom, or NR. 702 , In R 701 In the case of multiple occurrences, multiple adjacent R 701 They bond together to form substituted or unsubstituted monocyclic rings, or They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R that does not form the single ring and does not form the fused ring 701 and R 702 Each independently Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 701 and Ar 702 Each independently Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. L 701 for Substituted or unsubstituted alkylene groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted ynylene groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkylene groups with 3 to 50 carbon atoms Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. m1 is 0, 1, or 2. m2 can be 0, 1, 2, 3, or 4. m3 can be independently 0, 1, 2 or 3. Each m4 is independently 0, 1, 2, 3, 4, or 5. In R 701 In the case of multiple Rs, multiple Rs 701 They are the same or different. When multiple X7s exist, they may be identical or different from each other. In R 702 In the case of multiple Rs, multiple Rs 702 They are the same or different. In Ar 701 In the case of multiple instances, multiple Ar 701 They are the same or different. In Ar 702 In the case of multiple instances, multiple Ar 702 They are the same or different. In L 701 In the case of multiple Ls, multiple Ls 701 They are the same or different. In the general formula (8), R 801 With R 802 R 802 With R 803 and R 803 With R 804 At least one group in the group is bonded to each other to form a divalent group as shown in the following general formula (82). R 805 With R 806 R 806 With R 807 and R 807 With R 808 At least one group in the group is bonded to each other to form a divalent group as shown in the following general formula (83). R that does not form the divalent group shown in the general formula (82) 801 ~R 804 and R 811 ~R 814 At least one of them is a monovalent group represented by the following general formula (84), R that does not form the divalent group shown in the general formula (83) 805 ~R 808 and R 821 ~R 824 At least one of them is a monovalent group represented by the following general formula (84), X8 represents an oxygen atom, a sulfur atom, or NR. 809 , R that does not form the divalent groups shown in general formulas (82) and (83) and is not the monovalent group shown in general formula (84) 801 ~R 808 R is not a monovalent group represented by the general formula (84). 811 ~R 814 and R 821 ~R 824 and R 809 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the general formula (84), Ar 801 and Ar 802 Each independently Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. L 801 ~L 803 Each independently single bond, Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms Substituted or unsubstituted divalent heterocyclic groups with 5 to 30 cyclic atoms, or A divalent linker is formed by bonding 2 to 4 groups from the group consisting of a substituted or unsubstituted aryl group with 6 to 30 carbon atoms and a substituted or unsubstituted divalent heterocyclic group with 5 to 30 carbon atoms. In the general formula (84) This indicates the bonding position with the ring structure shown in general formula (8), or the group shown in general formula (82) or general formula (83). In the general formula (9), A 91 Ring and A 92 Each ring is independent of the others. Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted. Selected from A 91 Ring and A 92 One or more rings in the ring have the structure shown in the following general formula (92) bonding, In the general formula (92), A 93 Ring for Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted. 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, R 91 and R 92 for They bond together to form substituted or unsubstituted monocyclic rings, or They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R that does not form the single ring and does not form the fused ring 91 and R 92 and R 93 ~R 99 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the general formula (10), Ax1 ring is a ring of the general formula (10a) that is fused at any position between adjacent rings. Ax2 ring is a ring of the general formula (10b) that is fused at any position between adjacent rings. The two in the general formula (10b) Bonded to any position on the Ax3 ring, X A and X B Each independently is C(R) 1003 (R) 1004 ), Si(R) 1005 (R) 1006 ), oxygen atom or sulfur atom, Ax3 ring is Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 1001 for Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. R 1001 ~R 1006 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. mx1 is 3, mx2 is 2. Multiple R 1001 They are the same or different. Multiple R 1002 They are the same or different. ax is 0, 1, or 2. When ax is 0 or 1, the structures within the parentheses shown in "3-ax" are either identical or different. When ax = 2, multiple Ar 1001 They are the same or different. In the third or fourth compound, R 901 R 902 R 903 R 904 R 905 R 906 and R 907 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different. In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different. In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different. In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different. In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different. In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different. In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.
25. The organic electroluminescent element according to claim 1, wherein, R is not the group represented by the general formula (11) 101 ~R 110 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, or Substituted or unsubstituted cycloalkyl groups with 3 to 6 carbon atoms.
26. The organic electroluminescent element according to claim 1, wherein, R is not the group represented by the general formula (11) 101 ~R 110 It is a hydrogen atom.
27. The organic electroluminescent element according to claim 1 or 2, wherein, R 201 ~R 208 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, or Nitro, L 201 and L 202 Each independently single bond, Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 201 and Ar 202 Each independently Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
28. The organic electroluminescent element according to claim 1 or 2, wherein, L 201 and L 202 Each independently single key or Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms in a cyclic structure. Ar 201 and Ar 202 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure.
29. The organic electroluminescent element according to claim 1 or 2, wherein, Ar 201 and Ar 202 Each independently phenyl, Naphthyl, Fiki, Biphenyl, Triphenyl Diphenylfluorenyl, Dimethylfluorenyl, benzodiphenylfluorenyl, benzodimethylfluorenyl, Dibenzofuranyl, Dibenzothiophene group, Naphthobenzofuranyl, or Naphthobenzothiophene group.
30. The organic electroluminescent element according to claim 1 or 2, wherein, The second compound represented by general formula (2) is a compound represented by the following general formulas (201), (202), (203), (204), (205), (206), (207), (208), or (209). In the general formulas (201) to (209), L 201 and Ar 201 L in the general formula (2) 201 and Ar 201 Same meaning R 201 ~R 208 Each independently relates to R in the general formula (2). 201 ~R 208 They have the same meaning.
31. The organic electroluminescent element according to claim 1 or 2, wherein, In the second compound represented by general formula (2), R 201 ~R 208 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or -Si(R 901 (R) 902 (R) 903 The group shown is ).
32. The organic electroluminescent element according to claim 1 or 2, wherein, In the second compound represented by general formula (2), R 201 ~R 208 It is a hydrogen atom.
33. The organic electroluminescent element according to claim 1 or 2, wherein, In both the first and second compounds, the groups described as "substituted or unsubstituted" are all "unsubstituted" groups.
34. The organic electroluminescent element according to claim 1 or 2, wherein, The first light-emitting layer and the second light-emitting layer do not contain phosphorescent materials.
35. The organic electroluminescent element according to claim 1 or 2, wherein, The first luminescent layer and the second luminescent layer do not contain heavy metal complexes or phosphorescent rare earth metal complexes.
36. The organic electroluminescent element according to claim 1 or 2, wherein, Neither the first light-emitting layer nor the second light-emitting layer contains metal complexes.
37. The organic electroluminescent element according to claim 1 or 2, wherein, The electron mobility μH1 of the first compound and the electron mobility μH2 of the second compound satisfy the following mathematical expression (Mathematical Expression 3). μH2>μH1…(Mathematical formula 3).
38. The organic electroluminescent element according to claim 37, wherein, Electron mobility was determined using impedance spectroscopy using the following method: A measurement object layer with a thickness of 100nm to 200nm is held between an anode and a cathode. A bias DC voltage is applied while a small AC voltage below 100mV is applied simultaneously. The absolute value and phase of the AC current flowing under these conditions are measured. The measurement is performed while changing the frequency of the AC voltage. The complex impedance Z is calculated based on the current and voltage values. The frequency dependence of the imaginary part ImM of the modulus M = iωZ is then determined, where i is the imaginary unit and ω is the angular frequency. The reciprocal of the frequency ω at which ImM reaches its maximum value is defined as the response time of electrons conducted within the measurement object layer. Then, the electron mobility is calculated using the following formula. Electron mobility = (film thickness of the measured object layer) 2 / (Response time·voltage).
39. The organic electroluminescent element according to claim 1 or 2, wherein, A hole transport layer is provided between the anode and the first light-emitting layer.
40. The organic electroluminescent element according to claim 1 or 2, wherein, An electron transport layer is provided between the cathode and the second light-emitting layer.
41. An electronic device comprising the organic electroluminescent element according to any one of claims 1 to 40.
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