Compound, organic electroluminescence element, and electronic device
Patent Information
- Application Number
- CN202180073461.X
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2021-09-07
- Filing Date
- 2021-10-01
- Publication Date
- 2025-11-07
- Estimated Expiration
- 2041-10-01
AI Technical Summary
[0225]根据本发明的一个方案,能够提供能够提高有机EL元件的性能的化合物、包含该化合物的有机电致发光元件、以及搭载了该有机电致发光元件的电子设备。
Smart Images

Figure CN116348436B_ABST
Abstract
Description
TECHNICAL FIELD
[0001] The present application relates to a compound, an organic electroluminescent element, and an electronic device. BACKGROUND
[0002] An organic electroluminescent element (hereinafter sometimes referred to as "organic EL element") is applied to a full-color display of a mobile phone and a television, and the like. If a voltage is applied to the organic EL element, a hole is injected from an anode to a light-emitting layer, and an electron is injected from a cathode to the light-emitting layer. Then, in the light-emitting layer, the injected hole and the electron are recombined to form an exciton. At this time, according to a statistical law of electron spin, a singlet exciton is generated at a ratio of 25%, and a triplet exciton is generated at a ratio of 75%.
[0003] In order to achieve improvement in performance of the organic EL element, various studies have been made on a compound used for the organic EL element (for example, see Patent Documents 1 to 4). As the performance of the organic EL element, for example, luminance, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifetime can be cited.
[0004] PRIOR ART DOCUMENTS
[0005] PATENT DOCUMENTS
[0006] Patent Document 1: U.S. Patent Application Publication No. 2015 / 270498 Specification
[0007] Patent Document 2: U.S. Patent Application Publication No. 2015 / 001479 Specification
[0008] Patent Document 3: U.S. Patent Application Publication No. 2015 / 069344 Specification
[0009] Patent Document 4: U.S. Patent Application Publication No. 2017 / 331051 Specification SUMMARY
[0010] PROBLEMS TO BE SOLVED BY THE INVENTION
[0011] An object of the present application is to provide a compound capable of improving the performance of an organic EL element, an organic electroluminescent element including the compound, and an electronic device equipped with the organic electroluminescent element.
[0012] In addition, an object of the present application is to provide a compound, an organic electroluminescent element including the compound in a light-emitting layer on the anode side within a plurality of light-emitting layers, and an electronic device equipped with the organic electroluminescent element, which is capable of providing an element with a good balance between luminous efficiency and lifetime when used in a light-emitting layer on the anode side of an organic electroluminescent element in which a plurality of light-emitting layers are stacked.
[0013] MEANS FOR SOLVING THE PROBLEMS
[0014] According to one aspect of the present application, there is provided a compound having at least one group represented by the following general formula (11) and containing only one benzo[de]anthracene derivative skeleton represented by the following general formula (1000) in a molecule.
[0015] [Chemical Formula 1]
[0016]
[0017] (in the above general formula (1000),
[0018] X is an oxygen atom, a sulfur atom, C(R 2001 )(R 2002 ), or Si(R 2003 )(R 2004 ),
[0019] R 2001 and R 2004 each independently are
[0020] a hydrogen atom,
[0021] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[0022] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[0023] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,
[0024] a substituted or unsubstituted cyclic alkyl group having a ring-constituting carbon number of 3 to 50,
[0025] a group represented by -Si(R 901 )(R 902 )(R 903 ),
[0026] a group represented by -O-(R 904 ),
[0027] a group represented by -S-(R 905 ),
[0028] a group represented by -N(R 906 )(R 907 ),
[0029] a halogen atom,
[0030] a cyano group,
[0031] a nitro group,
[0032] a substituted or unsubstituted aryl group having a ring-constituting carbon number of 6 to 50, or
[0033] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,
[0034] R 10 , R 19 , or R
[0035] are linked to each other to form a substituted or unsubstituted monocyclic ring,
[0036] are linked to each other to form a substituted or unsubstituted fused ring, or
[0037] are not linked to each other,
[0038] R 10 , R 19 , or R
[0039] a hydrogen atom,
[0040] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
[0041] a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,
[0042] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
[0043] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
[0044] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
[0045] -Si(R 901 )(R 902 )(R 903 ),
[0046] -O-(R 904 ),
[0047] -S-(R 905 ),
[0048] -N(R 906 )(R 907 ),
[0049] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,
[0050] -C(=O)R 801 ,
[0051] -COOR 802 ,
[0052] a halogen atom,
[0053] Nitro,
[0054] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[0055] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[0056] The groups represented by the above general formula (11),
[0057] Among them, R 10 ~R 19 At least one of them is a group represented by the general formula (11) above.
[0058] 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.
[0059] L1 is
[0060] Substituted or unsubstituted arylene groups with 6 to 15 carbon atoms, or
[0061] Divalent heterocyclic groups with 5 to 15 cyclic atoms, substituted or unsubstituted.
[0062] mx is 1, 2, or 3.
[0063] When there are two or more L1 values, the two or more L1 values are either the same or different.
[0064] Ar1 is an aryl group containing four or more rings, either substituted or unsubstituted.
[0065] When there are two or more Ar1 values, the two or more Ar1 values are either the same or different from each other.
[0066] In the above general formula (11), * represents the bonding position.
[0067] In the compounds represented by the above general formula (1000), R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently
[0068] hydrogen atom,
[0069] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0070] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0071] substituted or unsubstituted aryl group having 6 to 50 ring-forming carbons, or
[0072] substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,
[0073] in the case where a plurality of R 901 in the case where a plurality of R 901 are the same or different from each other,
[0074] in the case where a plurality of R 902 in the case where a plurality of R 902 are the same or different from each other,
[0075] in the case where a plurality of R 903 in the case where a plurality of R 903 are the same or different from each other,
[0076] in the case where a plurality of R 904 in the case where a plurality of R 904 are the same or different from each other,
[0077] in the case where a plurality of R 905 in the case where a plurality of R 905 are the same or different from each other,
[0078] in the case where a plurality of R 906 in the case where a plurality of R 906 are the same or different from each other,
[0079] in the case where a plurality of R 907 in the case where a plurality of R 907 are the same or different from each other,
[0080] in the case where a plurality of R 801 in the case where a plurality of R 801 are the same or different from each other,
[0081] in the case where a plurality of R 802 in the case where a plurality of R 802 are the same or different from each other.
[0082] According to an aspect of the present application, there is provided a compound having at least one group represented by the following general formula (110A) and containing only one benzo[de]anthracene derivative skeleton represented by the following general formula (1000A) in a molecule.
[0083] [Chemical Formula 2]
[0084]
[0085] (in the above general formula (1000A),
[0086] X is an oxygen atom, a sulfur atom, C(R 2001(R) 2002 ), or Si(R) 2003 (R) 2004 ),
[0087] R 2001 ~R 2004 Each independently
[0088] hydrogen atom,
[0089] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0090] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0091] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0092] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0093] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0094] -O-(R 904 The groups shown in the figure,
[0095] -S-(R 905 The groups shown in the figure,
[0096] -N(R 906 (R) 907 The groups shown in the figure,
[0097] Halogen atoms,
[0098] cyano,
[0099] Nitro,
[0100] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0101] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0102] By R 10 ~R 19 One or more groups consisting of two or more adjacent elements.
[0103] They bond together to form substituted or unsubstituted monocyclic rings.
[0104] They bond together to form substituted or unsubstituted fused rings, or
[0105] They are not mutually bonded.
[0106] R 10 ~R 19 each independently is
[0107] a hydrogen atom,
[0108] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[0109] a substituted or unsubstituted haloalkyl group having a carbon number of 1 to 50,
[0110] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[0111] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,
[0112] a substituted or unsubstituted cyclic alkyl group having a ring-forming carbon number of 3 to 50,
[0113] a group represented by -Si(R 901 )(R 902 )(R 903 ),
[0114] a group represented by -O-(R 904 ),
[0115] a group represented by -S-(R 905 ),
[0116] a group represented by -N(R 906 )(R 907 ),
[0117] a substituted or unsubstituted aralkyl group having a carbon number of 7 to 50,
[0118] a group represented by -C(=O)R 801 ,
[0119] a group represented by -COOR 802 ,
[0120] a halogen atom,
[0121] a nitro group,
[0122] a substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50,
[0123] a substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50, or
[0124] a group represented by the above general formula (110A),
[0125] wherein at least one of R 13 and R 18 is a group represented by the above general formula (110A),
[0126] In the case where a plurality of groups represented by General Formula (110A) are present, the plurality of groups represented by General Formula (110A) are the same as or different from each other,
[0127] L 100 is
[0128] a single bond,
[0129] a substituted or unsubstituted arylene group having a ring-constituting carbon number of 6 to 50, or
[0130] a substituted or unsubstituted heterocyclic group having a ring-constituting atom number of 5 to 50,
[0131] mx is 1, 2, or 3,
[0132] In the case where a plurality of L 100 are present, the plurality of L 100 are the same as or different from each other,
[0133] Ar1 is a substituted or unsubstituted aryl group including 4 or more rings,
[0134] In the case where a plurality of Ar1 are present, the plurality of Ar1 are the same as or different from each other,
[0135] * in General Formula (110A) represents a bonding position,
[0136] In the compound represented by General Formula (1000A), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 , and R 802 are each independently
[0137] a hydrogen atom,
[0138] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[0139] a substituted or unsubstituted cycloalkyl group having a ring-constituting carbon number of 3 to 50,
[0140] a substituted or unsubstituted aryl group having a ring-constituting carbon number of 6 to 50, or
[0141] a substituted or unsubstituted heterocyclic group having a ring-constituting atom number of 5 to 50,
[0142] In the case where a plurality of R 901 are present, the plurality of R 901 are the same as or different from each other,
[0143] In the case where a plurality of R902 where a plurality of R 902 are the same or different from each other,
[0144] where a plurality of R 903 where a plurality of R 903 are the same or different from each other,
[0145] where a plurality of R 904 where a plurality of R 904 are the same or different from each other,
[0146] where a plurality of R 905 where a plurality of R 905 are the same or different from each other,
[0147] where a plurality of R 906 where a plurality of R 906 are the same or different from each other,
[0148] where a plurality of R 907 where a plurality of R 907 are the same or different from each other,
[0149] where a plurality of R 801 where a plurality of R 801 are the same or different from each other,
[0150] where a plurality of R 802 where a plurality of R 802 are the same or different from each other.
[0151] According to one embodiment of the present invention, there is provided an organic electroluminescent element including an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer including a light-emitting layer, at least one layer of the organic layer including a compound according to one embodiment of the present invention.
[0152] According to one embodiment of the present invention, there is provided an organic electroluminescent element including an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, the light-emitting layer including a first light-emitting layer and a second light-emitting layer, the first light-emitting layer containing a first compound, the first compound being a compound represented by the following general formula (1000B) and having at least one group represented by the following general formula (110).
[0153] [Chemical Formula 3]
[0154]
[0155] (in the above general formula (1000B),
[0156] X is an oxygen atom, a sulfur atom, C(R2001 (R) 2002 ), or Si(R) 2003 (R) 2004 ),
[0157] R 2001 ~R 2004 Each independently
[0158] hydrogen atom,
[0159] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0160] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0161] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0162] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0163] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0164] -O-(R 904 The groups shown in the figure,
[0165] -S-(R 905 The groups shown in the figure,
[0166] -N(R 906 (R) 907 The groups shown in the figure,
[0167] Halogen atoms,
[0168] cyano,
[0169] Nitro,
[0170] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0171] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0172] By R 10 ~R 19 One or more groups consisting of two or more adjacent elements.
[0173] They bond together to form substituted or unsubstituted monocyclic rings.
[0174] They bond together to form substituted or unsubstituted fused rings, or
[0175] They are not mutually bonded.
[0176] R 10 ~R 19 each independently is
[0177] a hydrogen atom,
[0178] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[0179] a substituted or unsubstituted haloalkyl group having a carbon number of 1 to 50,
[0180] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[0181] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,
[0182] a substituted or unsubstituted cyclic alkyl group having a ring-forming carbon number of 3 to 50,
[0183] a group represented by -Si(R 901 )(R 902 )(R 903 ),
[0184] a group represented by -O-(R 904 ),
[0185] a group represented by -S-(R 905 ),
[0186] a group represented by -N(R 906 )(R 907 ),
[0187] a substituted or unsubstituted aralkyl group having a carbon number of 7 to 50,
[0188] a group represented by -C(=O)R 801 ,
[0189] a group represented by -COOR 802 ,
[0190] a halogen atom,
[0191] a nitro group,
[0192] a substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50,
[0193] a substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50, or
[0194] a group represented by the above general formula (110),
[0195] wherein at least one of R 10 ~R 19 is a group represented by the above general formula (110),
[0196] In the case where a plurality of groups represented by General Formula (110) are present, the plurality of groups represented by General Formula (110) are the same as or different from each other,
[0197] L 100 is
[0198] a single bond,
[0199] a substituted or unsubstituted arylene group having a ring-forming carbon number of 6 to 50, or
[0200] a substituted or unsubstituted divalent heterocyclic group having a ring-forming atom number of 5 to 50,
[0201] mx is 1, 2, or 3,
[0202] In the case where L 100 is present two or more times, the two or more L 100 are the same as or different from each other,
[0203] Ar 100 is
[0204] a substituted or unsubstituted aryl group containing three or more rings, or
[0205] a substituted or unsubstituted heterocyclic group containing two or more aromatic rings and one or more heterocyclic rings,
[0206] Ar 100 does not contain an anthracene ring,
[0207] In the case where Ar 100 is present two or more times, the two or more Ar 100 are the same as or different from each other,
[0208] * in General Formula (110) represents a bonding position,
[0209] In the first compound represented by General Formula (1000B), R 901、 R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 , and R 802 are each independently
[0210] a hydrogen atom,
[0211] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[0212] a substituted or unsubstituted cycloalkyl group having a ring-forming carbon number of 3 to 50,
[0213] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbons, or
[0214] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,
[0215] in the case where a plurality of R 901 in the case where a plurality of R 901 are the same or different from each other,
[0216] in the case where a plurality of R 902 in the case where a plurality of R 902 are the same or different from each other,
[0217] in the case where a plurality of R 903 in the case where a plurality of R 903 are the same or different from each other,
[0218] in the case where a plurality of R 904 in the case where a plurality of R 904 are the same or different from each other,
[0219] in the case where a plurality of R 905 in the case where a plurality of R 905 are the same or different from each other,
[0220] in the case where a plurality of R 906 in the case where a plurality of R 906 are the same or different from each other,
[0221] in the case where a plurality of R 907 in the case where a plurality of R 907 are the same or different from each other,
[0222] in the case where a plurality of R 801 in the case where a plurality of R 801 are the same or different from each other,
[0223] in the case where a plurality of R 802 in the case where a plurality of R 802 are the same or different from each other.
[0224] According to one embodiment of the present application, there is provided an electronic device equipped with an organic electroluminescent element according to one embodiment of the present application.
[0225] According to one embodiment of the present application, there is provided an organic electroluminescent element capable of improving the performance of an organic EL element, and an electronic device equipped with the organic electroluminescent element.
[0226] In addition, according to one embodiment of the present application, a compound, an organic electroluminescent element including the compound in a light-emitting layer on the anode side among a plurality of light-emitting layers, and an electronic device equipped with the organic electroluminescent element, which can provide a balance between luminous efficiency and lifetime when used in a light-emitting layer on the anode side of an organic electroluminescent element in which a plurality of light-emitting layers are stacked, can be provided. BRIEF DESCRIPTION OF DRAWINGS
[0227] Figure 1 is a view showing a schematic configuration of an organic electroluminescent element according to one embodiment of the present application. DETAILED DESCRIPTION
[0228] [DEFINITIONS]
[0229] In the present specification, a hydrogen atom means isotopes including a neutron number, i.e., protium, deuterium, and tritium.
[0230] In the present specification, in a chemical structural formula, a bondable position of a symbol such as "R" and "D" indicating a deuterium atom is set to be bonded to a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom.
[0231] In the present specification, the number of ring-forming carbons means the number of carbon atoms among atoms constituting a ring itself in a compound in which atoms are bonded in a ring shape (for example, a monocyclic compound, a fused ring compound, a bridged ring compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon included in the substituent is not included in the number of ring-forming carbons. The "number of ring-forming carbons" described below is similarly set unless otherwise specified. For example, the number of ring-forming carbons of a benzene ring is 6, the number of ring-forming carbons of a naphthalene ring is 10, the number of ring-forming carbons of a pyridine ring is 5, and the number of ring-forming carbons of a furan ring is 4. In addition, for example, the number of ring-forming carbons of a 9,9-diphenylfluorenyl group is 13, and the number of ring-forming carbons of a 9,9'-spirobifluorenyl group is 25.
[0232] In addition, when an alkyl group is substituted as a substituent on a benzene ring, for example, the number of carbons of the alkyl group is not included in the number of ring-forming carbons of the benzene ring. Therefore, the number of ring-forming carbons of a benzene ring substituted with an alkyl group is 6. In addition, when an alkyl group is substituted as a substituent on a naphthalene ring, for example, the number of carbons of the alkyl group is not included in the number of ring-forming carbons of the naphthalene ring. Therefore, the number of ring-forming carbons of a naphthalene ring substituted with an alkyl group is 10.
[0233] In the present specification, the number of ring-forming atoms refers to the number of atoms constituting the ring itself in a compound having a structure in which atoms are bonded in a ring shape (e.g., monocyclic compounds, fused ring compounds, bridged ring compounds, carbocyclic compounds, and heterocyclic compounds) (e.g., monocyclic compounds, fused ring compounds, bridged ring compounds, carbocyclic compounds, and heterocyclic compounds). Atoms not constituting the ring (e.g., hydrogen atoms capping the bonds to the atoms constituting the ring), and atoms contained in substituents when the ring is substituted with a substituent are not included in the number of ring-forming atoms. The "number of ring-forming atoms" described below is similarly defined unless otherwise specified. For example, the number of ring-forming atoms of a pyridine ring is 6, the number of ring-forming atoms of a quinazoline ring is 10, and the number of ring-forming atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or the number of atoms constituting a substituent is not included in the number of ring-forming atoms of a pyridine ring. Thus, the number of ring-forming atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. In addition, for example, the number of hydrogen atoms bonded to a carbon atom of a quinazoline ring or the number of atoms constituting a substituent is not included in the number of ring-forming atoms of a quinazoline ring. Thus, the number of ring-forming atoms of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.
[0234] In the present specification, "carbon number XX ~ YY of a ZZ group which is substituted or unsubstituted" in the expression means the carbon number of the ZZ group when it is unsubstituted, and the carbon number of the substituent is not included when substitution has occurred. Here, "YY" is greater than "XX", "XX" refers to an integer of 1 or more, and "YY" refers to an integer of 2 or more.
[0235] In the present specification, "atom number XX ~ YY of a ZZ group which is substituted or unsubstituted" in the expression means the atom number of the ZZ group when it is unsubstituted, and the atom number of the substituent is not included when substitution has occurred. Here, "YY" is greater than "XX", "XX" refers to an integer of 1 or more, and "YY" refers to an integer of 2 or more.
[0236] In the present specification, an unsubstituted ZZ group means the case where "substituted or unsubstituted ZZ group" is "unsubstituted ZZ group", and a substituted ZZ group means the case where "substituted or unsubstituted ZZ group" is "substituted ZZ group".
[0237] In the present specification, "unsubstituted" in the expression "substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group is not replaced with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.
[0238] In addition, in the present specification, "substitution" in the expression "substituted or unsubstituted ZZ group" means that 1 or more hydrogen atoms in the ZZ group are replaced with a substituent. "Substitution" in the expression "BB group substituted with AA group" also similarly means that 1 or more hydrogen atoms in the BB group are replaced with an AA group.
[0239] "Substituent group described in the present specification"
[0240] The substituent group described in the present specification is explained below.
[0241] The ring-forming carbon number of "unsubstituted aryl group" described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification.
[0242] The ring-forming atom number of "unsubstituted heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in the present specification.
[0243] The carbon number of "unsubstituted alkyl group" described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in the present specification.
[0244] The carbon number of "unsubstituted alkenyl group" described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified in the present specification.
[0245] The carbon number of "unsubstituted alkynyl group" described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified in the present specification.
[0246] The ring-forming carbon number of "unsubstituted cycloalkyl group" described in the present specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified in the present specification.
[0247] The ring-forming carbon number of "unsubstituted arylene group" described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification.
[0248] The ring-forming atom number of "unsubstituted divalent heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in the present specification.
[0249] The carbon number of "unsubstituted alkylene group" described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in the present specification.
[0250] • "Substituted or unsubstituted aryl group"
[0251] As specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in the present specification, the following unsubstituted aryl groups (specific example group G1A) and substituted aryl groups (specific example group G1B) and the like can be given. (Here, the unsubstituted aryl group means the case where the "substituted or unsubstituted aryl group" is "unsubstituted aryl group", and the substituted aryl group means the case where the "substituted or unsubstituted aryl group" is "substituted aryl group".) In the present specification, only when described as "aryl group", both of "unsubstituted aryl group" and "substituted aryl group" are included.
[0252] The "substituted aryl group" means a group in which 1 or more hydrogen atoms of the "unsubstituted aryl group" have been replaced with a substituent. As the "substituted aryl group", for example, a group in which 1 or more hydrogen atoms of the "unsubstituted aryl group" of the following specific example group G1A have been replaced with a substituent, and the examples of the substituted aryl groups of the following specific example group G1B and the like can be given. Note that the examples of the "unsubstituted aryl group" and the examples of the "substituted aryl group" listed here are only one example, and the "substituted aryl group" described in the present specification also includes a group in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group" of the following specific example group G1B has been further replaced with a substituent, and a group in which a hydrogen atom of the substituent in the "substituted aryl group" of the following specific example group G1B has been further replaced with a substituent.
[0253] • Unsubstituted aryl groups (specific example group G1A):
[0254] phenyl,
[0255] p-biphenyl,
[0256] m-biphenyl,
[0257] o-biphenyl,
[0258] p-terphenyl-4-yl,
[0259] p-terphenyl-3-yl,
[0260] p-terphenyl-2-yl,
[0261] m-terphenyl-4-yl,
[0262] m-terphenyl-3-yl,
[0263] m-terphenyl-2-yl,
[0264] o-terphenyl-4-yl,
[0265] o-terphenyl-3-yl,
[0266] o-terphenyl-2-yl,
[0267] 1-naphthyl,
[0268] 2-naphthyl,
[0269] anthryl,
[0270] benzanthryl,
[0271] phenanthryl,
[0272] benzophenanthryl,
[0273] phenalenyl,
[0274] pyrenyl,
[0275] phenalenyl,
[0276] benzo phenalenyl,
[0277] triphenylenyl,
[0278] benztriphenylenyl,
[0279] tetracenyl,
[0280] pentacenyl,
[0281] fluorenyl,
[0282] 9,9'-spirobifluorenyl,
[0283] benzofluorenyl,
[0284] dibenzo fluorenyl,
[0285] fluoranthenyl,
[0286] benzofluoranthenyl,
[0287] perylenyl, and
[0288] a monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).
[0289] [Chemical Formula 4]
[0290]
[0291] [Chemical Formula 5]
[0292]
[0293] • Substituted aryl group (Specific example group G1B):
[0294] o-tolyl,
[0295] m-tolyl,
[0296] p-tolyl,
[0297] p-tolyl,
[0298] m-tolyl,
[0299] o-tolyl,
[0300] p-cumyl,
[0301] m-cumyl,
[0302] o-cumyl,
[0303] p-tert-butylphenyl,
[0304] m-tert-butylphenyl,
[0305] o-tert-butylphenyl,
[0306] 3,4,5-trimethylphenyl,
[0307] 9,9-dimethylfluorenyl,
[0308] 9,9-diphenylfluorenyl,
[0309] 9,9-bis(4-methylphenyl)fluorenyl,
[0310] 9,9-bis(4-tert-butylphenyl)fluorenyl,
[0311] cyano phenyl,
[0312] triphenylsilyl phenyl,
[0313] trimethylsilyl phenyl,
[0314] phenylnaphthyl,
[0315] naphthyl phenyl, and
[0316] one or more hydrogen atoms of a monovalent group derived from the ring structure represented by General Formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.
[0317] • "substituted or unsubstituted heterocyclic group"
[0318] The "heterocyclic group" described in the present specification is a cyclic group containing at least one hetero atom in a ring-forming atom. As specific examples of the hetero atom, a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom can be given.
[0319] The "heterocyclic group" described in the present specification is a monocyclic group or a fused ring group.
[0320] The "heterocyclic group" described in the present specification is a monocyclic group or a fused ring group.
[0321] The "heterocyclic group" described in the present specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.
[0322] As specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in the present specification, the following unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B) and the like can be given. (Here, the unsubstituted heterocyclic group refers to a case where the "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to a case where the "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group".) In the present specification, only the expression "heterocyclic group" includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group".
[0323] The "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of the "unsubstituted heterocyclic group" have been replaced with a substituent. Specific examples of the "substituted heterocyclic group" can be given as a group in which the hydrogen atoms of the "unsubstituted heterocyclic group" of the following specific example group G2A have been replaced, and examples of the substituted heterocyclic group of the following specific example group G2B, and the like. Note that the examples of the "unsubstituted heterocyclic group" and the examples of the "substituted heterocyclic group" given here are only one example, and the "substituted heterocyclic group" described in the present specification also includes a group in which the hydrogen atom bonded to the ring-forming atom of the heterocyclic group itself of the "substituted heterocyclic group" of the specific example group G2B has been further replaced with a substituent, and a group in which the hydrogen atom of the substituent of the "substituted heterocyclic group" of the specific example group G2B has been further replaced with a substituent.
[0324] The specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).
[0325] The specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of the monovalent heterocyclic groups derived from the ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) have been replaced with a substituent (specific example group G2B4).
[0326] • unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1):
[0327] a pyrrolyl group,
[0328] imidazolyl,
[0329] pyrazolyl,
[0330] triazolyl,
[0331] tetrazolyl,
[0332] oxazolyl,
[0333] isoxazolyl,
[0334] oxadiazolyl,
[0335] thiazolyl,
[0336] isothiazolyl,
[0337] thiadiazolyl,
[0338] pyridyl,
[0339] pyridazinyl,
[0340] pyrimidinyl,
[0341] pyrazinyl,
[0342] triazinyl,
[0343] indolyl,
[0344] isoindolyl,
[0345] indolizinyl,
[0346] quinolizinyl,
[0347] quinolyl,
[0348] isoquinolyl,
[0349] cinnolinyl,
[0350] phthalazinyl,
[0351] quinazolinyl,
[0352] quinoxalinyl,
[0353] benzimidazolyl,
[0354] indazolyl,
[0355] phenanthrolinyl,
[0356] phenanthridinyl,
[0357] acridinyl,
[0358] phenoxazinyl,
[0359] carbazolyl,
[0360] benzocarbazolyl,
[0361] morpholinyl,
[0362] phenoxazinyl,
[0363] phenothiazinyl,
[0364] azacarbazolyl, and
[0365] diazacarbazolyl.
[0366] • unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2):
[0367] furanyl,
[0368] oxazolyl,
[0369] isoxazolyl,
[0370] oxadiazolyl,
[0371] xanthenyl,
[0372] benzofuranyl,
[0373] isobenzofuranyl,
[0374] dibenzofuranyl,
[0375] naphthobenzofuranyl,
[0376] benzoxazolyl,
[0377] benzisoxazolyl,
[0378] phenoxazinyl,
[0379] morpholinyl,
[0380] dinaphthofuranyl,
[0381] azadibenzofuranyl,
[0382] diazadibenzofuranyl,
[0383] azanaphthobenzofuranyl, and
[0384] diazanaphthobenzofuranyl.
[0385] • unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3):
[0386] thienyl,
[0387] thiazolyl,
[0388] isothiazolyl,
[0389] thiadiazolyl,
[0390] benzothienyl,
[0391] isobenzothienyl,
[0392] dibenzothienyl,
[0393] naphthobenzothienyl,
[0394] benzothiazolyl,
[0395] benzoisothiazolyl,
[0396] phenothiazinyl,
[0397] dinaphthothienyl,
[0398] azadibenzothienyl,
[0399] diazadibenzothienyl,
[0400] azanaphthobenzothienyl, and
[0401] diazanaphthobenzothienyl.
[0402] • a monovalent heterocyclic group derived by removing one hydrogen atom from a ring structure represented by General Formulae (TEMP-16) to (TEMP-33) below (specific examples group G2A4):
[0403] [Chemical Formula 6]
[0404]
[0405] [Chemical Formula 7]
[0406]
[0407] In General Formulae (TEMP-16) to (TEMP-33) above, X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH2. Among them, at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.
[0408] In General Formulae (TEMP-16) to (TEMP-33) above, X A and Y AWhen at least any one of R1to R4of the above general formula (TEMP-16) to (TEMP-33) is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the above general formula (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.
[0409] • Substituted heterocyclic group containing a nitrogen atom (Specific example group G2B1):
[0410] (9-phenyl)carbazolyl,
[0411] (9-biphenyl)carbazolyl,
[0412] (9-phenyl)phenylcarbazolyl,
[0413] (9-naphthyl)carbazolyl,
[0414] diphenylcarbazol-9-yl,
[0415] phenylcarbazol-9-yl,
[0416] methylbenzoimidazolyl,
[0417] ethylbenzoimidazolyl,
[0418] phenyltriazinyl,
[0419] biphenyltriazinyl,
[0420] diphenyltriazinyl,
[0421] phenylquinazolinyl, and
[0422] biphenylquinazolinyl.
[0423] • Substituted heterocyclic group containing an oxygen atom (Specific example group G2B2):
[0424] phenyldibenzofuranyl,
[0425] methyldibenzofuranyl,
[0426] tert-butyldibenzofuranyl, and
[0427] a monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].
[0428] • Substituted heterocyclic group containing a sulfur atom (Specific example group G2B3):
[0429] phenyldibenzothiophenyl,
[0430] methyldibenzothiophenyl,
[0431] tert-butyldibenzothiophenyl, and
[0432] a monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].
[0433] • a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by General Formulae (TEMP-16) to (TEMP-33) described above have been replaced with a substituent (specific example group G2B4):
[0434] The "one or more hydrogen atoms of a monovalent heterocyclic group" refers to one or more hydrogen atoms selected from the hydrogen atoms bonded to the ring- forming carbon atoms of the monovalent heterocyclic group, the hydrogen atoms bonded to the nitrogen atom when at least either one of X A and Y A is NH, and the hydrogen atoms of the methylene group when one of X A and Y A is CH2.
[0435] • "substituted or unsubstituted alkyl group"
[0436] As specific examples of the "substituted or unsubstituted alkyl group" described in the present specification (specific example group G3), the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B) can be given. (Here, the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group", and the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group".) Hereinafter, only when expressed as "alkyl group", both the "unsubstituted alkyl group" and the "substituted alkyl group" are included.
[0437] The "substituted alkyl group" refers to a group in which one or more hydrogen atoms of the "unsubstituted alkyl group" have been replaced with a substituent. As specific examples of the "substituted alkyl group", examples of a group in which one or more hydrogen atoms of the "unsubstituted alkyl group" (specific example group G3A) described below have been replaced with a substituent, and examples of the substituted alkyl group (specific example group G3B) can be given. In the present specification, the alkyl group of the "unsubstituted alkyl group" refers to a chain-shaped alkyl group. Therefore, the "unsubstituted alkyl group" includes both the straight-chain "unsubstituted alkyl group" and the branched-chain "unsubstituted alkyl group". Note that the examples of the "unsubstituted alkyl group" and the examples of the "substituted alkyl group" given here are merely examples, and the "substituted alkyl group" described in the present specification also includes a group in which the hydrogen atoms of the alkyl group itself of the "substituted alkyl group" of specific example group G3B have been further replaced with a substituent, and a group in which the hydrogen atoms of the substituents of the "substituted alkyl group" of specific example group G3B have been further replaced with a substituent.
[0438] • unsubstituted alkyl group (specific example group G3A):
[0439] methyl group,
[0440] ethyl group,
[0441] n-propyl,
[0442] i-propyl,
[0443] n-butyl,
[0444] i-butyl,
[0445] s-butyl, and
[0446] t-butyl.
[0447] • Substituted alkyl (Specific Example Group G3B): heptafluoropropyl group (including isomers),
[0448] pentafluoroethyl group,
[0449] 2,2,2-trifluoroethyl group, and
[0450] trifluoromethyl group.
[0451] • "Substituted or unsubstituted alkenyl group"
[0452] As specific examples of the "substituted or unsubstituted alkenyl group" described in the present specification (Specific Example Group G4), the following unsubstituted alkenyl groups (Specific Example Group G4A) and substituted alkenyl groups (Specific Example Group G4B) and the like can be given. (Here, the unsubstituted alkenyl group means the case where the "substituted or unsubstituted alkenyl group" is "unsubstituted alkenyl group", and the substituted alkenyl group means the case where the "substituted or unsubstituted alkenyl group" is "substituted alkenyl group".) In the present specification, only when it is expressed as "alkenyl group", both of "unsubstituted alkenyl group" and "substituted alkenyl group" are included.
[0453] The "substituted alkenyl group" means a group in which 1 or more hydrogen atoms in the "unsubstituted alkenyl group" are replaced with a substituent. As specific examples of the "substituted alkenyl group", examples of a group in which the "unsubstituted alkenyl group" (Specific Example Group G4A) has a substituent and examples of the substituted alkenyl group (Specific Example Group G4B) and the like can be given. Note that the examples of the "unsubstituted alkenyl group" and the examples of the "substituted alkenyl group" listed here are only examples, and the "substituted alkenyl group" described in the present specification also includes a group in which the hydrogen atom of the alkenyl group itself in the "substituted alkenyl group" of Specific Example Group G4B is further replaced with a substituent and a group in which the hydrogen atom of the substituent in the "substituted alkenyl group" of Specific Example Group G4B is further replaced with a substituent.
[0454] • Unsubstituted alkenyl group (Specific Example Group G4A):
[0455] vinyl group,
[0456] allyl group,
[0457] 1-butenyl group,
[0458] 2-butenyl group, and
[0459] 3-butenyl group.
[0460] • Substituted alkenyl group (Specific example group G4B):
[0461] 1,3-butadienyl group,
[0462] 1-methylvinyl group,
[0463] 1-methylallyl group,
[0464] 1,1-dimethylallyl group,
[0465] 2-methylallyl group, and
[0466] 1,2-dimethylallyl group.
[0467] • "Substituted or unsubstituted alkynyl group"
[0468] As specific examples of the "substituted or unsubstituted alkynyl group" recited in the present specification (specific example group G5), the following unsubstituted alkynyl groups (specific example group G5A) and the like can be given. (Here, the unsubstituted alkynyl group means the case where the "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group".) In the present specification, only when expressed as "alkynyl group", both "unsubstituted alkynyl group" and "substituted alkynyl group" are included.
[0469] The "substituted alkynyl group" means a group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" have been replaced with a substituent group. As specific examples of the "substituted alkynyl group", a group in which one or more hydrogen atoms in the following "unsubstituted alkynyl group" (specific example group G5A) have been replaced with a substituent group and the like can be given.
[0470] • Unsubstituted alkynyl group (specific example group G5A):
[0471] ethynyl group
[0472] • "Substituted or unsubstituted cycloalkyl group"
[0473] As specific examples of the "substituted or unsubstituted cycloalkyl group" recited in the present specification (specific example group G6), the following unsubstituted cycloalkyl groups (specific example group G6A) and substituted cycloalkyl groups (specific example group G6B) and the like can be given. (Here, the unsubstituted cycloalkyl group means the case where the "substituted or unsubstituted cycloalkyl group" is "unsubstituted cycloalkyl group", and the substituted cycloalkyl group means the case where the "substituted or unsubstituted cycloalkyl group" is "substituted cycloalkyl group".) In the present specification, only when expressed as "cycloalkyl group", both "unsubstituted cycloalkyl group" and "substituted cycloalkyl group" are included.
[0474] "Substituted aryl group" means a group in which one or more hydrogen atoms of "unsubstituted aryl group" have been replaced with a substituent. As specific examples of "substituted aryl group", examples of a group in which one or more hydrogen atoms of the above-described "unsubstituted aryl group" (specific example group G5A) have been replaced with a substituent, and the like can be given. Note that the examples of "unsubstituted aryl group" and "substituted aryl group" given here are merely examples, and "substituted aryl group" described in the present specification also includes a group in which one or more hydrogen atoms of the aryl group itself of "substituted aryl group" of specific example group G5B have been replaced with a substituent, and a group in which a hydrogen atom of the substituent of "substituted aryl group" of specific example group G5B has been further replaced with a substituent.
[0475] • Unsubstituted heteroaromatic group (specific example group G8A):
[0476] • Substituted heteroaromatic group (specific example group G8B):
[0477] • Unsubstituted heteroaromatic group (specific example group G8A):
[0478] • Substituted heteroaromatic group (specific example group G8B):
[0479] • Unsubstituted heteroaromatic group (specific example group G8A):
[0480] • Substituted heteroaromatic group (specific example group G8B):
[0481] • Unsubstituted heteroaromatic group (specific example group G8A):
[0482] • Substituted heteroaromatic group (specific example group G8B):
[0483] • Unsubstituted heteroaromatic group (specific example group G8A):
[0484] • Substituted heteroaromatic group (specific example group G8B):
[0485] • Unsubstituted heteroaromatic group (specific example group G8A):
[0486] • Substituted heteroaromatic group (specific example group G8B): 901 902 903
[0487] As specific examples of the group represented by -Si(R 901 )(R 902 )(R 903 ) described in the present specification (specific example group G7), the following can be given:
[0488] • -Si(G1)(G1)(G1),
[0489] • -Si(G1)(G2)(G2),
[0490] • -Si(G1)(G1)(G2),
[0491] -Si(G2)(G2)(G2),
[0492] -Si(G3)(G3)(G3), and
[0493] -Si(G6)(G6)(G6). In this case,
[0494] G1is "substituted or unsubstituted aryl group" described in the specific example group G1.
[0495] G2is "substituted or unsubstituted heterocyclic group" described in the specific example group G2.
[0496] G3is "substituted or unsubstituted alkyl group" described in the specific example group G3.
[0497] G6is "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.
[0498] The plurality of G1in -Si(G1)(G1)(G1) are the same or different from each other.
[0499] The plurality of G2in -Si(G1)(G2)(G2) are the same or different from each other.
[0500] The plurality of G1in -Si(G1)(G1)(G2) are the same or different from each other.
[0501] The plurality of G2in -Si(G2)(G2)(G2) are the same or different from each other.
[0502] The plurality of G3in -Si(G3)(G3)(G3) are the same or different from each other.
[0503] The plurality of G6in -Si(G6)(G6)(G6) are the same or different from each other.
[0504] • a group represented by -O-(R 904 ) described in the present specification
[0505] As a specific example (specific example group G8) of the group represented by -O-(R 904 ) described in the present specification, the following can be given.
[0506] -O(G1),
[0507] -O(G2),
[0508] -O(G3), and
[0509] -O(G6).
[0510] In this case,
[0511] G1is "substituted or unsubstituted aryl group" described in the specific example group G1.
[0512] G2 is "substituted or unsubstituted heterocyclic group" described in the group of specific examples G2.
[0513] G3 is "substituted or unsubstituted alkyl group" described in the group of specific examples G3.
[0514] G6 is "substituted or unsubstituted cycloalkyl group" described in the group of specific examples G6.
[0515] • a group represented by "-S-(R 905 ) in the present specification"
[0516] As a specific example of the group represented by "-S-(R 905 ) in the present specification (group of specific examples G9), there can be mentioned
[0517] -S(G1),
[0518] -S(G2),
[0519] -S(G3), and
[0520] -S(G6).
[0521] Here,
[0522] G1 is "substituted or unsubstituted aryl group" described in the group of specific examples G1.
[0523] G2 is "substituted or unsubstituted heterocyclic group" described in the group of specific examples G2.
[0524] G3 is "substituted or unsubstituted alkyl group" described in the group of specific examples G3.
[0525] G6 is "substituted or unsubstituted cycloalkyl group" described in the group of specific examples G6.
[0526] • a group represented by "-N(R 906 )(R 907 ) in the present specification"
[0527] As a specific example of the group represented by "-N(R 906 )(R 907 ) in the present specification (group of specific examples G10), there can be mentioned
[0528] -N(G1)(G1),
[0529] -N(G2)(G2),
[0530] -N(G1)(G2),
[0531] -N(G3)(G3), and
[0532] -N(G6)(G6).
[0533] In this specification,
[0534] G1is "substituted or unsubstituted aryl" described in the group of specific examples G1.
[0535] G2is "substituted or unsubstituted heterocyclic group" described in the group of specific examples G2.
[0536] G3is "substituted or unsubstituted alkyl" described in the group of specific examples G3.
[0537] G6is "substituted or unsubstituted cycloalkyl" described in the group of specific examples G6.
[0538] A plurality of G1in -N(G1)(G1) are the same or different from each other.
[0539] A plurality of G2in -N(G2)(G2) are the same or different from each other.
[0540] A plurality of G3in -N(G3)(G3) are the same or different from each other.
[0541] A plurality of G6in -N(G6)(G6) are the same or different from each other.
[0542] • "halogen atom"
[0543] As a specific example (group of specific examples G11) of "halogen atom" described in the present specification, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like can be given.
[0544] • "substituted or unsubstituted fluoroalkyl group"
[0545] The "substituted or unsubstituted fluoroalkyl group" described in the present specification means a group in which at least one hydrogen atom bonded to a carbon atom constituting an alkyl group in the "substituted or unsubstituted alkyl group" has been replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to a carbon atom constituting an alkyl group in the "substituted or unsubstituted alkyl group" have been replaced with a fluorine atom (perfluoro group). The carbon number of the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification. The "substituted fluoroalkyl group" means a group in which one or more hydrogen atoms of the "fluoroalkyl group" have been replaced with a substituent. Note that the "substituted fluoroalkyl group" described in the present specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom constituting an alkyl chain in the "substituted fluoroalkyl group" have been further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in the "substituted fluoroalkyl group" have been further replaced with a substituent. As a specific example of the "unsubstituted fluoroalkyl group", examples in which one or more hydrogen atoms of the above "alkyl group" (group of specific examples G3) have been replaced with a fluorine atom can be given.
[0546] • "Substituted or unsubstituted haloalkyl group"
[0547] The "substituted or unsubstituted haloalkyl group" described in the present specification means a group in which at least one hydrogen atom bonded to a carbon atom constituting an alkyl group in the "substituted or unsubstituted alkyl group" has been replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to a carbon atom constituting an alkyl group in the "substituted or unsubstituted alkyl group" have been replaced with halogen atoms. The carbon number of the "unsubstituted haloalkyl group" is, unless otherwise specified in the present specification, 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The "substituted haloalkyl group" means a group in which one or more hydrogen atoms of the "haloalkyl group" have been replaced with a substituent. Note that the "substituted haloalkyl group" described in the present specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain of the "substituted haloalkyl group" have been further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent of the "substituted haloalkyl group" have been further replaced with a substituent. As specific examples of the "unsubstituted haloalkyl group", examples of a group in which one or more hydrogen atoms of the above-described "alkyl group" (specific example group G3) have been replaced with a halogen atom, and the like can be given. The haloalkyl group is sometimes referred to as a halogenated alkyl group.
[0548] • "Substituted or unsubstituted alkoxy group"
[0549] As a specific example of the "substituted or unsubstituted alkoxy group" described in the present specification, a group represented by -O(G3) is given, where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The carbon number of the "unsubstituted alkoxy group" is, unless otherwise specified in the present specification, 1 to 50, preferably 1 to 30, and more preferably 1 to 18.
[0550] • "Substituted or unsubstituted alkylthio group"
[0551] As a specific example of the "substituted or unsubstituted alkylthio group" described in the present specification, a group represented by -S(G3) is given, where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The carbon number of the "unsubstituted alkylthio group" is, unless otherwise specified in the present specification, 1 to 50, preferably 1 to 30, and more preferably 1 to 18.
[0552] • "Substituted or unsubstituted aryloxy group"
[0553] As a specific example of the "substituted or unsubstituted aryloxy group" described in the present specification, a group represented by -O(G1) is given, where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. The ring-constituting carbon number of the "unsubstituted aryloxy group" is, unless otherwise specified in the present specification, 6 to 50, preferably 6 to 30, and more preferably 6 to 18.
[0554] • "substituted or unsubstituted arylthio group"
[0555] As a specific example of the "substituted or unsubstituted arylthio group" recited in the present specification, a group represented by -S(G1) is exemplified, where G1 is the "substituted or unsubstituted aryl group" recited in the specific example group G1. The ring-forming carbon number of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless specifically stated otherwise in the present specification.
[0556] • "substituted or unsubstituted trialkylsilyl group"
[0557] As a specific example of the "trialkylsilyl group" recited in the present specification, a group represented by -Si(G3)(G3)(G3) is exemplified, where G3 is the "substituted or unsubstituted alkyl group" recited in the specific example group G3. The plurality of G3 in -Si(G3)(G3)(G3) are the same or different from each other. The carbon number of each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless specifically stated otherwise in the present specification.
[0558] • "substituted or unsubstituted aralkyl group"
[0559] As a specific example of the "substituted or unsubstituted aralkyl group" recited in the present specification, a group represented by -(G3)-(G1) is exemplified, where G3 is the "substituted or unsubstituted alkyl group" recited in the specific example group G3, and G1 is the "substituted or unsubstituted aryl group" recited in the specific example group G1. Thus, the "aralkyl group" is a group in which the hydrogen atom of the "alkyl group" is replaced with the "aryl group" as a substituent, and is one of the "substituted alkyl groups". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with the "unsubstituted aryl group", and the carbon number of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless specifically stated otherwise in the present specification.
[0560] As a specific example of the "substituted or unsubstituted aralkyl group", a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butyl group, an α-naphthylmethyl group, a 1-α-naphthylethyl group, a 2-α-naphthylethyl group, a 1-α-naphthylisopropyl group, a 2-α-naphthylisopropyl group, a β-naphthylmethyl group, a 1-β-naphthylethyl group, a 2-β-naphthylethyl group, a 1-β-naphthylisopropyl group, and a 2-β-naphthylisopropyl group, and the like can be exemplified.
[0561] The substituted or unsubstituted aryl group described in the present specification is preferably a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, and a 9,9-diphenylfluorenyl group, and the like, unless otherwise specified in the present specification.
[0562] The substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, or 9-carbazolyl), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an azadibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl, (9-phenyl)carbazol-2-yl, (9-phenyl)carbazol-3-yl, or (9-phenyl)carbazol-4-yl), a (9-biphenyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazinyl group, a biphenyltriazinyl group, a diphenyltriazinyl group, a phenyldibenzofuranyl group, and a phenyldibenzothiophenyl group, and the like, unless otherwise specified in the present specification.
[0563] In the present specification, the carbazolyl group is specifically any one of the following, unless otherwise specified in the present specification.
[0564] [Chemical Formula 8]
[0565]
[0566] In the present specification, the (9-phenyl)carbazolyl group is specifically any one of the following, unless otherwise specified in the present specification.
[0567] [Chemical Formula 9]
[0568]
[0569] In General Formulas (TEMP-Czl) to (TEMP-Cz9) above, * indicates a bonding position.
[0570] In the present specification, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any one of the following, unless otherwise specified in the present specification.
[0571] [Chemical Formula 10]
[0572]
[0573] In General Formulae (TEMP-34) to (TEMP-41) above, * indicates a bonding position.
[0574] The substituted or unsubstituted alkyl group described in the present specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, or the like, unless otherwise specified in the present specification.
[0575] • "Substituted or unsubstituted arylene"
[0576] The "substituted or unsubstituted arylene" described in the present specification, unless otherwise specified, is a divalent group derived by removing one hydrogen atom from the aryl ring of the above "substituted or unsubstituted aryl group". As specific examples (specific example group G12) of the "substituted or unsubstituted arylene", there can be mentioned a divalent group derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described in the specific example group G1, and the like.
[0577] • "Substituted or unsubstituted divalent heterocyclic group"
[0578] The "substituted or unsubstituted divalent heterocyclic group" described in the present specification, unless otherwise specified, is a divalent group derived by removing one hydrogen atom from the heterocyclic ring of the above "substituted or unsubstituted heterocyclic group". As specific examples (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group", there can be mentioned a divalent group derived by removing one hydrogen atom from the heterocyclic ring of the "substituted or unsubstituted heterocyclic group" described in the specific example group G2, and the like.
[0579] • "Substituted or unsubstituted alkylene"
[0580] The "substituted or unsubstituted alkylene" described in the present specification, unless otherwise specified, is a divalent group derived by removing one hydrogen atom from the alkyl chain of the above "substituted or unsubstituted alkyl group". As specific examples (specific example group G14) of the "substituted or unsubstituted alkylene", there can be mentioned a divalent group derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl group" described in the specific example group G3, and the like.
[0581] The substituted or unsubstituted arylene described in the present specification is preferably any one of the groups of General Formulae (TEMP-42) to (TEMP-68), unless otherwise specified in the present specification.
[0582] [Chemical Formula 11]
[0583]
[0584] [Chemical Formula 12]
[0585]
[0586] In General Formulae (TEMP-42) to (TEMP-52) above, Q1to Q 10 each independently is a hydrogen atom or a substituent.
[0587] In General Formulae (TEMP-42) to (TEMP-52) above, * indicates a bonding position.
[0588] [Chemical Formula 13]
[0589]
[0590] In General Formulae (TEMP-53) to (TEMP-62) above, Q1to Q 10 each independently is a hydrogen atom or a substituent.
[0591] Q9and Q 10 may be bonded to each other via a single bond to form a ring.
[0592] In General Formulae (TEMP-53) to (TEMP-62) above, * indicates a bonding position.
[0593] [Chemical Formula 14]
[0594]
[0595] In General Formulae (TEMP-63) to (TEMP-68) above, Q1to Q8each independently is a hydrogen atom or a substituent.
[0596] In General Formulae (TEMP-63) to (TEMP-68) above, * indicates a bonding position.
[0597] The substituted or unsubstituted bivalent heterocyclic group described in the present specification is preferably any one of the groups of General Formulae (TEMP-69) to (TEMP-102) below, unless otherwise specified in the present specification.
[0598] [Chemical Formula 15]
[0599]
[0600] [Chemical Formula 16]
[0601]
[0602] [Chemical Formula 17]
[0603]
[0604] In General Formulae (TEMP-69) to (TEMP-82), Q1to Q9are each independently a hydrogen atom or a substituent.
[0605] [Chemical Formula 18]
[0606]
[0607] [Chemical Formula 19]
[0608]
[0609] [Chemical Formula 20]
[0610]
[0611] [Chemical Formula 21]
[0612]
[0613] In General Formulae (TEMP-83) to (TEMP-102), Q1to Q8are each independently a hydrogen atom or a substituent.
[0614] The above is a description of the "substituent described in the present specification".
[0615] • "case where bonded to form a ring"
[0616] In the present specification, the expression "one or more groups each consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other" means the case where "one or more groups each consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring", the case where "one or more groups each consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted fused ring", and the case where "one or more groups each consisting of two or more adjacent groups are not bonded to each other".
[0617] Hereinafter, the case where "one or more groups each consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more groups each consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases are sometimes collectively referred to as "case where bonded to form a ring") in the present specification will be described. The case of an anthracene compound represented by the following General Formula (TEMP-103) in which the parent skeleton is an anthracene ring will be described.
[0618] [Chemical Formula 22]
[0619]
[0620] For example, in the case where "one or more groups of two or more groups adjacent to each other are bonded to each other to form a ring" is included in R 921 ~R 930 , a group of two groups adjacent to each other means a group of R 921 and R 922 , a group of R 922 and R 923 , a group of R 923 and R 924 , a group of R 924 and R 930 , a group of R 930 and R 925 , a group of R 925 and R 926 , a group of R 926 and R 927 , a group of R 927 and R 928 , a group of R 928 and R 929 , and a group of R 929 and R 921 .
[0621] The above "one or more groups" means that two or more groups of two or more groups adjacent to each other can form a ring at the same time. For example, in the case where R 921 and R 922 are bonded to each other to form a ring Q A , and R 925 and R 926 are bonded to each other to form a ring Q B at the same time, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).
[0622] [Chemical Formula 23]
[0623]
[0624] The case where "a group of two or more groups adjacent to each other" forms a ring includes not only the case where a group of "two" groups adjacent to each other is bonded, as in the above example, but also the case where a group of "three or more" groups adjacent to each other is bonded. For example, it means that R 921 and R 922 are bonded to each other to form a ring Q A , and R 922 and R 923 are bonded to each other to form a ring Q C , a group of three groups (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 .
[0625] [Chemical Formula 24]
[0626]
[0627] In the formed "single ring" or "fused ring," the structure of the ring alone can be either a saturated ring or an unsaturated ring. Even when a "single ring" or "fused ring" is formed from "one group of two adjacent rings," the "single ring" or "fused ring" can still form a saturated ring or an unsaturated ring. For example, the ring Q formed in the above general formula (TEMP-104) A and ring Q B Each is either a "single ring" or a "fused ring". Additionally, the ring Q formed in the above general formula (TEMP-105) A and Q ring C It is a "fused ring". The ring Q of the above general formula (TEMP-105) A With ring Q C Through ring Q A With ring Q C Fusing together forms a fused ring. The ring Q of the above general formula (TMEP-104) A If it is a benzene ring, then ring Q A It is a single ring. The ring Q in the above general formula (TMEP-104) A If it is a naphthalene ring, then ring Q A It is a fused ring.
[0628] "Unsaturated rings" refer to aromatic hydrocarbon rings or aromatic heterocycles. "Saturated rings" refer to aliphatic hydrocarbon rings or non-aromatic heterocycles.
[0629] 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.
[0630] 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.
[0631] 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.
[0632] "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.
[0633] 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.
[0634] 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.
[0635] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".
[0636] Unless otherwise stated in this specification, "unsaturated ring" is preferred over "saturated ring".
[0637] Unless otherwise stated in this specification, "monocyclic" is preferably a benzene ring.
[0638] Unless otherwise stated in this specification, the "unsaturated ring" is preferably a benzene ring.
[0639] In the case of "one or more selected from the group of 2 or more adjacent groups" or "mutually bonded to form a substituted or unsubstituted monocyclic ring" or "mutually bonded to form a substituted or unsubstituted fused ring", unless otherwise specified in the specification, one or more selected from the group of 2 or more adjacent groups are preferably mutually bonded to form a substituted or unsubstituted "unsaturated ring" formed of a plurality of atoms of the parent skeleton and one or more and 15 or less elements selected from the group consisting of carbon, nitrogen, oxygen, and sulfur.
[0640] The substituent in the case where the above "monocyclic ring" or "fused ring" has a substituent is, for example, the "optional substituent" described later. Specific examples of the substituent in the case where the above "monocyclic ring" or "fused ring" has a substituent are the substituents described in the item of "substituents described in the specification" above.
[0641] The substituent in the case where the above "saturated ring" or "unsaturated ring" has a substituent is, for example, the "optional substituent" described later. Specific examples of the substituent in the case where the above "monocyclic ring" or "fused ring" has a substituent are the substituents described in the item of "substituents described in the specification" above.
[0642] The above is a description of the case of "one or more selected from the group of 2 or more adjacent groups mutually bonded to form a substituted or unsubstituted monocyclic ring" and the case of "one or more selected from the group of 2 or more adjacent groups mutually bonded to form a substituted or unsubstituted fused ring" ("the case of bonded to form a ring").
[0643] • Substituents in the case of "substituted or unsubstituted"
[0644] In one embodiment of the present specification, the above substituent in the case of "substituted or unsubstituted" (hereinafter referred to as "optional substituent" in the specification.) is, for example, one or more selected from the group consisting of an unsubstituted alkyl group having a carbon number of 1 to 50,
[0645] an unsubstituted alkenyl group having a carbon number of 2 to 50,
[0646] an unsubstituted alkynyl group having a carbon number of 2 to 50,
[0647] an unsubstituted cycloalkyl group having a ring-forming carbon number of 3 to 50,
[0648] -Si(R 901 )(R 902 )(R 903 ),
[0649] -O-(R 904 ),
[0650] -S-(R 905 ),
[0651] -N(R 906 (R) 907 ),
[0652] Halogen atom, cyano group, nitro group,
[0653] Unsubstituted aryl groups with 6 to 50 carbon atoms and
[0654] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms
[0655] Groups, etc., in the composition group
[0656] Here, R 901 ~R 907 Each independently
[0657] hydrogen atom,
[0658] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0659] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0660] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0661] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[0662] R 901 When there are more than two, more than two R 901 They are the same or different.
[0663] R 902 When there are more than two, more than two R 902 They are the same or different.
[0664] R 903 When there are more than two, more than two R 903 They are the same or different.
[0665] R 904 When there are more than two, more than two R 904 They are the same or different.
[0666] R 905 When there are more than two, more than two R 905 They are the same or different.
[0667] R 906 When there are more than two, more than two R 906 They are the same or different.
[0668] R 907When there are two or more, two or more of R 907 are the same or different.
[0669] In one embodiment, the substituent when the above expression is "substituted or unsubstituted" is a group selected from the group consisting of
[0670] an alkyl group having a carbon number of 1 to 50,
[0671] an aryl group having a ring-forming carbon number of 6 to 50, and
[0672] a heterocyclic group having a ring-forming atom number of 5 to 50.
[0673] In one embodiment, the substituent when the above expression is "substituted or unsubstituted" is a group selected from the group consisting of
[0674] an alkyl group having a carbon number of 1 to 18,
[0675] an aryl group having a ring-forming carbon number of 6 to 18, and
[0676] a heterocyclic group having a ring-forming atom number of 5 to 18.
[0677] Specific examples of each of the groups of the above optional substituent are the specific examples of the substituents described in the item of "Substituents described in the present specification" above.
[0678] In the present specification, unless otherwise specified, "saturated ring" or "unsaturated ring" can be formed by adjacent optional substituents to each other, preferably substituted or unsubstituted saturated five-membered ring, substituted or unsubstituted saturated six-membered ring, substituted or unsubstituted unsaturated five-membered ring, or substituted or unsubstituted unsaturated six-membered ring, more preferably benzene ring.
[0679] In the present specification, unless otherwise specified, the optional substituent can further have a substituent. As the substituent further having the optional substituent, the same as the above optional substituent.
[0680] In the present specification, the numerical range represented by "AA to BB" means a range including the lower limit value AA recited before "AA to BB" and the upper limit value BB recited after "AA to BB".
[0681] [First Embodiment]
[0682] (Compound)
[0683] The compound related to the present embodiment is a compound having at least one group represented by the following general formula (110) and represented by the following general formula (1000B).
[0684] [Chemical Formula 25]
[0685]
[0686] (in the above general formula (1000B),
[0687] X is an oxygen atom, a sulfur atom, C(R 2001 )(R 2002 ) or Si(R 2003 )(R 2004 ),
[0688] one or more groups selected from the group consisting of 2 or more adjacent groups of R 10 to R 19
[0689] are bonded to each other to form a substituted or unsubstituted monocyclic ring,
[0690] are bonded to each other to form a substituted or unsubstituted fused ring, or
[0691] are not bonded to each other,
[0692] R 10 to R 19 are each independently
[0693] a hydrogen atom,
[0694] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[0695] a substituted or unsubstituted haloalkyl group having a carbon number of 1 to 50,
[0696] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[0697] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,
[0698] a substituted or unsubstituted cyclic alkyl group having a ring-forming carbon number of 3 to 50,
[0699] a group represented by -Si(R 901 )(R 902 )(R 903 ),
[0700] a group represented by -O-(R 904 ),
[0701] a group represented by -S-(R 905 ),
[0702] a group represented by -N(R 906 )(R 907 ),
[0703] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0704] -C(=O)R 801 The groups shown
[0705] -COOR 802 The groups shown
[0706] Halogen atoms,
[0707] Nitro,
[0708] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[0709] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[0710] The groups represented by the above general formula (110),
[0711] Among them, R 10 ~R 19 At least one of them is a group represented by the general formula (110) above.
[0712] When there are multiple groups represented by the above general formula (110), the multiple groups represented by the above general formula (110) may be the same as or different from each other.
[0713] L 100 for
[0714] single bond,
[0715] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[0716] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0717] mx is 1, 2, or 3.
[0718] In L 100 When there are more than two, more than two L 100 They are the same or different.
[0719] Ar 100 for
[0720] substituted or unsubstituted aryl groups containing three or more rings, or
[0721] A substituted or unsubstituted heterocyclic group comprising two or more aromatic rings and one or more heterocyclic rings.
[0722] Ar 100 It does not contain anthracene rings.
[0723] In Ar 100 In the case of two or more Ar, two or more Ar100 are the same or different from each other,
[0724] * in General Formula (110) represents a bonding site.
[0725] The compound represented by General Formula (1000B) is preferably a compound having at least one group represented by General Formula (110) and represented by General Formula (100).
[0726] [Chemical Formula 26]
[0727]
[0728] (In General Formula (100), R 10 ~R 19 each independently R 10 ~R 19 have the same meaning, wherein R 10 ~R 19 none of groups each consisting of 2 or more adjacent ones of R 100 , L 100 and mx have the same meaning as Ar 100 , L 100 and mx in General Formula (110).
[0729] The LUMO (Lowest Unoccupied Molecular Orbital) of a compound in which a cyano group is directly bonded to a benzoxanthene ring (referred to as a cyano-substituted benzoxanthene compound) is lower than that of a compound in which no cyano group is bonded to the benzoxanthene ring. In the case where a cyano-substituted benzoxanthene compound is used as a host material of a light-emitting layer, damage to the host material at the interface on the hole-transporting layer side of the light-emitting layer increases, and the lifetime of an organic EL element can decrease. In particular, it is not suitable to use a cyano-substituted benzoxanthene compound for a light-emitting layer on the hole-transporting layer side in an organic EL element in which a plurality of light-emitting layers are stacked.
[0730] The compound according to the present embodiment is also preferably represented by General Formula (101) or General Formula (102).
[0731] [Chemical Formula 27]
[0732]
[0733] [Chemical Formula 28]
[0734]
[0735] (In General Formula (101) and General Formula (102), R 10 ~R19 Each independently relates to R in the above general formula (1000B) 10 ~R 19 The meanings are the same, where R 10 ~R 19 In Ar, groups consisting of two or more adjacent elements are not bonded to each other. 100 L 100 And mx are respectively related to Ar in the above general formula (110) 100 L 100 (Same meaning as mx)
[0736] In the compounds involved in this embodiment, R is not a group represented by the general formula (110) described above. 10 ~R 19 Each of the following is preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
[0737] In the compounds involved in this embodiment, R is not a group represented by the general formula (110) described above. 10 ~R 19 Hydrogen atoms are preferred.
[0738] In the compounds involved in this embodiment, L 100 Preferably, it is a single bond, or a substituted or unsubstituted aryl group containing three or fewer benzene rings.
[0739] In the compounds involved in this embodiment, L 100 The preferred form is anthracene group that is neither substituted nor substituted.
[0740] In the compounds involved in this embodiment, L 100 Single bonds are also preferred.
[0741] In the compounds involved in this embodiment, -(L) in the above general formula (110) 100 ) mx - The group shown is preferably a group shown in any of the following general formulas (111) to (120).
[0742] [Chemical Formula 29]
[0743]
[0744]
Chemical Formula 30
[0745]
[0746] (In the above general formulas (111) to (120), * indicates the bonding position.)
[0747] The group represented by -(L 100 ) mx The group represented by -(L
[0748] In the compound according to the present embodiment, Ar 100 is preferably a substituted or unsubstituted aryl group condensed with 4 or more benzene rings.
[0749] In the compound according to the present embodiment, Ar 100 is preferably a substituted or unsubstituted aryl group condensed with 4 benzene rings, or a substituted or unsubstituted aryl group condensed with 5 benzene rings.
[0750] In the compound according to the present embodiment, Ar 100 is preferably a group represented by General Formula (1100), (1200), (1300), (1400), (1500), (1600), (1700), or (1800).
[0751] [Chemical Formula 31]
[0752]
[0753] [Chemical Formula 32]
[0754]
[0755] [Chemical Formula 33]
[0756]
[0757] [Chemical Formula 34]
[0758]
[0759] (In General Formula (1100), R 111 to R 120 one of which is a bond,
[0760] (In General Formula (1200), R 1201 to R 1212 one of which is a bond,
[0761] (In General Formula (1300), R 130l to R 1314 one of which is a bond,
[0762] (In General Formula (1400), R 1401 to R 1414 one of which is a bond,
[0763] In the above general formula (1500), R 1501 ~R 1514 One of them is a connection key.
[0764] In the above general formula (1600), R 160] ~R 1612 One of them is a connection key.
[0765] In the above general formula (1700), R 1701 ~R 1710 One of them is a connection key.
[0766] In the above general formula (1800), R 1801 ~R 1812 One of them is a connection key.
[0767] R is not a connection key 111 ~R 120 R is not a connection key. 1201 ~R 1212 R is not a connection key. 1301 ~R 1314 R is not a connection key. 1401 ~R 1414 R is not a connection key. 1501 ~R 1514 R is not a connection key. 1601 ~R 1612 R is not a connection key. 1701 ~R 1710 And R, which is not a connection key. 1801 ~R 1812 Each independently
[0768] hydrogen atom,
[0769] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0770] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0771] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0772] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0773] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0774] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0775] -O-(R 904 The groups shown in the figure,
[0776] -S-(R 905 The groups shown in the figure,
[0777] -N(R 906 (R) 907 The groups shown in the figure,
[0778] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0779] -C(=O)R 801 The groups shown
[0780] -COOR 802 The groups shown
[0781] Halogen atoms,
[0782] Nitro,
[0783] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0784] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[0785] The groups represented by the above general formula (1100) in R 111 In the case of a connecting bond, it is a group represented by the following general formula (1112), in R 120 In the case of a connecting bond, it is a group represented by the following general formula (1113), in R 119 In the case of a connecting bond, it is a group represented by the following general formula (1114).
[0786]
Chemical Formula 35
[0787]
[0788] (In the above general formulas (1112), (1113), and (1114),
[0789] R 111 ~R 120 Each independently
[0790] hydrogen atom,
[0791] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0792] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0793] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0794] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0795] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
[0796] a group represented by -Si(R 901 )(R 902 )(R 903 ),
[0797] a group represented by -O-(R 904 ),
[0798] a group represented by -S-(R 905 ),
[0799] a group represented by -N(R 906 )(R 907 ),
[0800] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,
[0801] a group represented by -C(=O)R 801 ,
[0802] a group represented by -COOR 802 ,
[0803] a halogen atom,
[0804] a nitro group,
[0805] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or
[0806] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,
[0807] the * in the above general formulae (1112) to (1114) represents a bonding position.
[0808] In the compound concerned in the present embodiment, R 111 to R 120 , R 1201 to R 1212 , R 1301 to R 1314 , R 1401 to R 1414 , R 1501 to R 1514 , R 1601 to R 1612 , R 1701 to R 1710 , and R 1801 to R 1812each independently is preferably a hydrogen atom, a substituted or unsubstituted alkyl group with a carbon number of 1 to 50, a substituted or unsubstituted cycloalkyl group with a ring-constituting carbon number of 3 to 50, or a substituted or unsubstituted aryl group with a ring-constituting carbon number of 6 to 50.
[0809] In the compound according to the present embodiment, R 111 ~R 120 , R 1201 ~R 1212 , R 1301 ~R 1314 , R 1401 ~R 1414 , R 1501 ~R 1514 , R 1601 ~R 1612 , R 1701 ~R 1710 , and R 1801 ~R 1812 is preferably a hydrogen atom.
[0810] In the compound according to the present embodiment, Ar 100 For example, a substituted or unsubstituted benzoxanthene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group is also preferable.
[0811] The compound according to the present embodiment preferably does not contain a cyano group in the molecule.
[0812] The compound according to the present embodiment also preferably contains only one or two benzoxanthene rings in the molecule.
[0813] In addition, the compound according to the present embodiment also preferably contains only one benzoxanthene ring in the molecule.
[0814] The compound according to the present embodiment also preferably is a compound having at least one group represented by the following general formula (11) and containing only one benz[de]anthracene derivative skeleton represented by the following general formula (1000) in the molecule.
[0815]
Chemical Formula 36
[0816]
[0817] (In the above general formula (1000),
[0818] X is an oxygen atom, a sulfur atom, C(R 2001 )(R 2002), or Si(R 2003 )(R 2004 ),
[0819] consisting of 2 or more adjacent groups selected from the group consisting of R 10 to R 19
[0820] bonded to each other to form a substituted or unsubstituted monocyclic ring,
[0821] bonded to each other to form a substituted or unsubstituted fused ring, or
[0822] not bonded to each other,
[0823] R 10 to R 19 are each independently
[0824] a hydrogen atom,
[0825] a substituted or unsubstituted alkyl group with a carbon number of 1 to 50,
[0826] a substituted or unsubstituted haloalkyl group with a carbon number of 1 to 50,
[0827] a substituted or unsubstituted alkenyl group with a carbon number of 2 to 50,
[0828] a substituted or unsubstituted alkynyl group with a carbon number of 2 to 50,
[0829] a substituted or unsubstituted cyclic alkyl group with a ring-forming carbon number of 3 to 50,
[0830] a group represented by -Si(R 901 )(R 902 )(R 903 ),
[0831] a group represented by -O-(R 904 ),
[0832] a group represented by -S-(R 905 ),
[0833] a group represented by -N(R 906 )(R 907 ),
[0834] a substituted or unsubstituted aralkyl group with a carbon number of 7 to 50,
[0835] a group represented by -C(=O)R 801 ,
[0836] a group represented by -COOR 802 ,
[0837] a halogen atom,
[0838] a nitro group,
[0839] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms,
[0840] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, or
[0841] a group represented by the above general formula (11),
[0842] wherein R 10 to R 19 are each independently the same as the meaning of R 10 to R 19 in the above general formula (1000), and at least one of R 10 to R 19 is a group represented by the above general formula (11),
[0843] in the case where a plurality of groups represented by the above general formula (11) are present, the plurality of groups represented by the above general formula (11) are the same as or different from each other,
[0844] L1is
[0845] a substituted or unsubstituted arylene group having 6 to 15 ring-forming carbon atoms, or
[0846] a substituted or unsubstituted divalent heterocyclic group having 5 to 15 ring-forming atoms,
[0847] mxis 1, 2 or 3,
[0848] in the case where two or more of L1are present, the two or more of L1are the same as or different from each other,
[0849] Ar1is a substituted or unsubstituted aryl group containing four or more rings,
[0850] in the case where two or more of Ar1are present, the two or more of Ar1are the same as or different from each other,
[0851] the * in the above general formula (11) indicates a bonding position.
[0852] The compound represented by the above general formula (1000) preferably has at least one group represented by the above general formula (11) and contains only one benzoxanthene ring represented by the above general formula (1) in the molecule.
[0853] [Chemical Formula 37]
[0854]
[0855] (in the above general formula (1), R 10 to R 19 are each independently the same as the meaning of R 10 to R 19 in the above general formula (1000), and at least one of R 10 to R 19 is a group represented by the above general formula (11).each of the groups consisting of 2 or more adjacent ones among the R
[0856] The compound represented by the above general formula (1) can suppress the decrease in hole mobility and the decrease in luminous efficiency of the organic EL element by having L1 which is an arylene group having 6 to 15 ring-forming carbon atoms or a divalent heterocyclic group having 5 to 15 ring-forming atoms between the benzoxanthene ring and Ar1 which is a substituted or unsubstituted aryl group having 4 or more rings.
[0857] The compound having at least one group represented by the above general formula (11) and having only one benzoxanthene ring represented by the above general formula (1) in the molecule is preferably represented by the following general formula (121) or general formula (122).
[0858] [Chemical Formula 38]
[0859]
[0860] [Chemical Formula 39]
[0861]
[0862] (in the above general formula (121) and general formula (122), R 10 to R 19 are each independently the same as R 10 to R 19 in the above general formula (1), Ar v , L1 and mx are each the same as Ar1, L1 and mx in the above general formula (11).
[0863] (in the above general formula (121), R 10 to R 12 , R 14 to R 19 are each independently the same as R
[0864] (in the above general formula (122), R 10 to R 17 , R 19 are each independently the same as R
[0865] (in the above general formula (1), R 10 to R 19 are each independently preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.
[0866] In the compound represented by General Formula (1) above, R 10 ~R 19 is preferably a hydrogen atom.
[0867] In the compound represented by General Formula (1) above, L1is preferably a substituted or unsubstituted arylene group containing 3 or less benzene rings.
[0868] In the compound represented by General Formula (1) above, L1is preferably not a substituted or unsubstituted anthrylene group.
[0869] In the compound represented by General Formula (1) above, the group represented by -(L1) mx in General Formula (11) above is preferably a group represented by any one of General Formulae (111) to (120) above.
[0870] In the compound represented by General Formula (1) above, the group represented by -(L1) mx in General Formula (11) above is preferably a group represented by General Formula (111) or (112) above.
[0871] A compound having at least one group represented by General Formula (11) above and containing only one benzo[de]anthracene derivative skeleton represented by General Formula (1000) in the molecule is also preferably represented by General Formula (123), General Formula (124), General Formula (125), or General Formula (126) below.
[0872] [Chemical Formula 40]
[0873]
[0874] [Chemical Formula 41]
[0875]
[0876] [Chemical Formula 42]
[0877]
[0878] [Chemical Formula 43]
[0879]
[0880] In General Formulae (123), (124), (125), and (126) above,
[0881] X is an oxygen atom, a sulfur atom, C(R 2001 )(R 2002 ), or Si(R 2003 )(R 2004),
[0882] R 2001 ~R 2004 each independently is
[0883] a hydrogen atom,
[0884] substituted or unsubstituted alkyl having a carbon number of 1 to 50,
[0885] substituted or unsubstituted alkenyl having a carbon number of 2 to 50,
[0886] substituted or unsubstituted alkynyl having a carbon number of 2 to 50,
[0887] substituted or unsubstituted cycloalkyl having a ring-forming carbon number of 3 to 50,
[0888] -Si(R 901 )(R 902 )(R 903 ) group,
[0889] -O-(R 904 ) group,
[0890] -S-(R 905 ) group,
[0891] -N(R 906 )(R 907 ) group,
[0892] a halogen atom,
[0893] a cyano group,
[0894] a nitro group,
[0895] substituted or unsubstituted aryl having a ring-forming carbon number of 6 to 50, or
[0896] substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50,
[0897] L 10 is
[0898] substituted or unsubstituted arylene having a ring-forming carbon number of 6 to 15, or
[0899] substituted or unsubstituted divalent heterocyclic group having a ring-forming atom number of 5 to 15,
[0900] Ar 10 is an aryl group having 4 or more condensed benzene rings,
[0901] Ar 11 is an aryl group having a ring-forming carbon number of 6 to 14,
[0902] wherein, Ar11 a substituted or unsubstituted anthryl group,
[0903] m10 is 5,
[0904] m11 is 6,
[0905] each Rm is independently
[0906] a hydrogen atom,
[0907] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[0908] a substituted or unsubstituted haloalkyl group having a carbon number of 1 to 50,
[0909] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[0910] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,
[0911] a substituted or unsubstituted cyclic alkyl group having a ring-forming carbon number of 3 to 50,
[0912] a group represented by -Si(R 901 )(R 902 )(R 903 ),
[0913] a group represented by -O-(R 904 ),
[0914] a group represented by -S-(R 905 ),
[0915] a group represented by -N(R 906 )(R 907 ),
[0916] a substituted or unsubstituted aralkyl group having a carbon number of 7 to 50,
[0917] a group represented by -C(=O)R 801 ,
[0918] a group represented by -COOR 802 ,
[0919] a halogen atom,
[0920] a nitro group,
[0921] a substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50, or
[0922] a substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50,
[0923] a plurality of Rm are not bonded to each other,
[0924] R 901 , R902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 each independently is
[0925] a hydrogen atom,
[0926] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[0927] a substituted or unsubstituted cycloalkyl group having a ring-constituting carbon number of 3 to 50,
[0928] a substituted or unsubstituted aryl group having a ring-constituting carbon number of 6 to 50, or
[0929] a substituted or unsubstituted heterocyclic group having a ring-constituting atom number of 5 to 50,
[0930] in the case where a plurality of R 901 exist, the plurality of R 901 are the same or different from each other,
[0931] in the case where a plurality of R 902 exist, the plurality of R 902 are the same or different from each other,
[0932] in the case where a plurality of R 903 exist, the plurality of R 903 are the same or different from each other,
[0933] in the case where a plurality of R 904 exist, the plurality of R 904 are the same or different from each other,
[0934] in the case where a plurality of R 905 exist, the plurality of R 905 are the same or different from each other,
[0935] in the case where a plurality of R 906 exist, the plurality of R 906 are the same or different from each other,
[0936] in the case where a plurality of R 907 exist, the plurality of R 907 are the same or different from each other,
[0937] in the case where a plurality of R 801 exist, the plurality of R 801 are the same or different from each other,
[0938] in the case where a plurality of R 802 exist, the plurality of R 802 are the same or different from each other.
[0939] As the compound represented by General Formula (123) and the compound represented by General Formula (125), Ar 11 (6 to 14 ring-forming carbons of an aryl group other than a substituted or unsubstituted anthryl group) is substituted on the benzo[de]anthracene derivative skeleton, the singlet energy S1 is reduced, and stabilization of the excited state can be expected, and thus a device using the compound can be long-lived.
[0940] As the compound represented by General Formula (124) and the compound represented by General Formula (126), Ar 11 (6 to 14 ring-forming carbons of an aryl group other than a substituted or unsubstituted anthryl group) is substituted on the benzo[de]anthracene derivative skeleton, the singlet energy S1 is reduced, and stabilization of the excited state can be expected, and thus a device using the compound can be long-lived. 10 (6 to 14 ring-forming carbons of an aryl group other than a substituted or unsubstituted anthryl group) is substituted on the benzo[de]anthracene derivative skeleton, the singlet energy S1 is reduced, and stabilization of the excited state can be expected, and thus a device using the compound can be long-lived.
[0941] The compound represented by General Formula (123) is more preferably represented by General Formula (1230). In addition, the compound represented by General Formula (124) is more preferably represented by General Formula (1240). In addition, the compound represented by General Formula (125) is more preferably represented by General Formula (1250). In addition, the compound represented by General Formula (126) is more preferably represented by General Formula (1260).
[0942] [Chemical Formula 44]
[0943]
[0944] [Chemical Formula 45]
[0945]
[0946] [Chemical Formula 46]
[0947]
[0948] [Chemical Formula 47]
[0949]
[0950] In General Formula (1230), General Formula (1240), General Formula (1250), and General Formula (1260), X, L 10 , Ar 10 , Ar 11 , m10, m11, and Rm are each independently L 10 , Ar 10 , Ar11 m10, m11 and Rm have the same meaning.
[0951] In the compounds represented by the above general formulas (123), (124), (125), (126), (1230), (1240), (1250), or (1260), X is preferably an oxygen atom.
[0952] In the compounds represented by the above general formulas (123), (124), (125), (126), (1230), (1240), (1250), or (1260), L 10 Preferably, it is a substituted or unsubstituted aryl group containing three or fewer benzene rings.
[0953] In the compounds represented by general formulas (123), (124), (125), (126), (1230), (1240), (1250), or (1260), -L 10 - The group shown is preferably a group shown in any of the above general formulas (111) to (120).
[0954] In the compounds represented by general formulas (123), (124), (125), (126), (1230), (1240), (1250), or (1260), -L 10 - The group shown is preferably the group shown in the above general formula (111) or (112).
[0955] The compounds involved in this embodiment are preferably compounds having at least one group represented by the following general formula (110A) and containing only one benzo[de]anthracene derivative skeleton represented by the following general formula (1000A) in the molecule.
[0956] [Chemical Formula 48]
[0957]
[0958] (In the above general formula (1000A),
[0959] X represents an oxygen atom, a sulfur atom, or a C(R) atom. 2001 (R) 2002 ), or Si(R) 2003 (R) 2004 ),
[0960] By R 10 ~R 19 One or more groups consisting of two or more adjacent elements.
[0961] are linked to each other to form a substituted or unsubstituted monocyclic ring,
[0962] are linked to each other to form a substituted or unsubstituted fused ring, or
[0963] are not linked to each other,
[0964] R is neither the above-mentioned substituted or unsubstituted monocyclic ring nor the above-mentioned substituted or unsubstituted fused ring 10 ~R 19 each independently is
[0965] a hydrogen atom,
[0966] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[0967] a substituted or unsubstituted haloalkyl group having a carbon number of 1 to 50,
[0968] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[0969] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,
[0970] a substituted or unsubstituted cyclic alkyl group having a ring-forming carbon number of 3 to 50,
[0971] -Si(R 901) (R 902 )(R 903 ) group,
[0972] an -O-(R 904 ) group,
[0973] an -S-(R 905 ) group,
[0974] an -N(R 906 )(R 907 ) group,
[0975] a substituted or unsubstituted aralkyl group having a carbon number of 7 to 50,
[0976] a -C(=O)R 801 group,
[0977] a -COOR 802 group,
[0978] a halogen atom,
[0979] a nitro group,
[0980] a substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50,
[0981] a substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50, or
[0982] the above-described group represented by General Formula (110A),
[0983] wherein R 13 and R 18 at least one of R
[0984] in the case where a plurality of the above-described groups represented by General Formula (110A) are present, the plurality of the above-described groups represented by General Formula (110A) are the same as or different from each other,
[0985] L 100 is
[0986] a single bond,
[0987] a substituted or unsubstituted arylene group having a ring-forming carbon number of 6 to 50, or
[0988] a substituted or unsubstituted divalent heterocyclic group having a ring-forming atom number of 5 to 50,
[0989] mx is 1, 2, or 3,
[0990] in the case where two or more L 100 are present, the two or more L 100 are the same as or different from each other,
[0991] Ar1 is a substituted or unsubstituted aryl group including 4 or more rings,
[0992] in the case where two or more Ar1 are present, the two or more Ar1 are the same as or different from each other,
[0993] the * in the above-described General Formula (110A) indicates a bonding position.
[0994] The compound represented by the above-described General Formula (1000A) preferably has at least one group represented by the above-described General Formula (110A) and includes only one benzoxanthene ring represented by the above-described General Formula (100A) in the molecule.
[0995]
Chemical Formula 49
[0996]
[0997] (in the above-described General Formula (100A), R 10 to R 19 each independently have the same meaning as R 10 to R 19 in the above-described General Formula (1000A), wherein R 10 to R 19each of the groups consisting of 2 or more adjacent ones among R
[0998] In the compound represented by General Formula (100A), R 13 and at least one of R 18 is a group including Ar1which is a substituted or unsubstituted aryl group including 4 or more rings. In this case, Ar1is bonded to the para position of the oxygen atom (O) of the benzoxanthene ring via a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 ring-forming atoms, whereby the hole-injection property of the compound according to the present embodiment is improved. Thus, an increase in the emission efficiency of an organic EL element using the compound according to the present embodiment can be expected.
[0999] The compound represented by General Formula (100A) is preferably represented by General Formula (121A) or General Formula (122A) below.
[1000] [Chemical Formula 50]
[1001]
[1002] [Chemical Formula 51]
[1003]
[1004] (In General Formula (121A) and General Formula (122A), R 10 to R 19 each independently have the same meaning as R 10 to R 19 in General Formula (100A), Ar1, L 100 and mx each have the same meaning as Ar1, L 100 and mx in General Formula (110A), respectively.)
[1005] In General Formula (121A), R 10 to R 12 , R 14 to R 19 are preferably not the groups represented by General Formula (110A).
[1006] In General Formula (122A), R 10 to R 17 , R 19 are preferably not the groups represented by General Formula (110A).
[1007] In the compound represented by General Formula (100A), R 10~R 19 each independently is preferably a hydrogen atom, a substituted or unsubstituted alkyl group with a carbon number of 1 to 50, a substituted or unsubstituted cycloalkyl group with a ring-constituting carbon number of 3 to 50, or a substituted or unsubstituted aryl group with a ring-constituting carbon number of 6 to 50.
[1008] In the compound represented by General Formula (100A), R 10 ~R 19 is preferably a hydrogen atom.
[1009] In the compound represented by General Formula (100A), L 100 is preferably a single bond, or a substituted or unsubstituted arylene group containing 3 or less benzene rings.
[1010] In the compound represented by General Formula (100A), -(L 100 ) mx is preferably a group represented by any one of General Formulae (111) to (120).
[1011] In the compound represented by General Formula (100A), -(L 100 ) mx is preferably a group represented by General Formula (111) or (112).
[1012] In the compound according to the present embodiment, Ar1is preferably a substituted or unsubstituted aryl group condensed with 4 or more benzene rings.
[1013] In the compound according to the present embodiment, Ar1or Ar 10 is preferably a substituted or unsubstituted aryl group condensed with 4 benzene rings, or a substituted or unsubstituted aryl group condensed with 5 benzene rings.
[1014] In the compound according to the present embodiment, Ar1or Ar 10 is preferably a group represented by General Formula (1100), (1200), (1300), (1400), (1500), (1600), (1700), or (1800).
[1015] In the compound according to the present embodiment, Ar1or Ar 10 is preferably a group represented by General Formula (1100) or (1200).
[1016] In the compound according to the present embodiment, each group described as "substituted or unsubstituted" is preferably an "unsubstituted" group.
[1017] In the compound (the compound represented by the above general formula (1000B), the compound represented by the above general formula (1000), the compound represented by the above general formula (1000A), etc.) according to the present embodiment, in a case where "one or more groups out of two or more adjacent groups are bonded to each other to form a ring (a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring)", the two adjacent groups are, for example, a group of R 10 ~R 19 In the compound (the compound represented by the above general formula (1000B), the compound represented by the above general formula (1000), the compound represented by the above general formula (1000A), etc.) according to the present embodiment, in a case where "one or more groups out of two or more adjacent groups are bonded to each other to form a ring (a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring)", the two adjacent groups are, for example, a group of R 10 and R 11 , a group of R 11 and R 12 , a group of R 12 and R 13 , a group of R 13 and R 14 , a group of R 14 and R 15 , a group of R 16 and R 17 , a group of R 17 and R 18 , a group of R 18 and R 19 , and a group of R 19 and R 10 .
[1018] In the compound (the compound represented by the above general formula (1000B), the compound represented by the above general formula (1000), the compound represented by the above general formula (1000A), etc.) according to the present embodiment, it is preferable that any one group out of a group of R 13 and R 14 , a group of R 16 and R 17 , and a group of R 19 and R 10 be bonded to each other to form a substituted or unsubstituted benzene ring.
[1019] In the compound (the compound represented by the above general formula (1000B), the compound represented by the above general formula (1000), the compound represented by the above general formula (1000A), etc.) according to the present embodiment, it is preferable that any one group out of a group of R
[1020] R 2001 ~R 2004 each independently be
[1021] a hydrogen atom,
[1022] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[1023] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[1024] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,
[1025] substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
[1026] -Si(R 901 )(R 902 )(R 903 ) group,
[1027] -O-(R 904 ) group,
[1028] -S-(R 905 ) group,
[1029] -N(R 906) (R 907 ) group,
[1030] a halogen atom,
[1031] a cyano group,
[1032] a nitro group,
[1033] substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or
[1034] substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
[1035] In the compound (the compound represented by General Formula (1000B) described above, the compound represented by General Formula (1000) described above, the compound represented by General Formula (1000A) described above, etc.) according to the present embodiment, preferably,
[1036] R 2001 and R 2004 are each independently
[1037] a hydrogen atom,
[1038] substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
[1039] a halogen atom,
[1040] a cyano group,
[1041] a nitro group,
[1042] substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or
[1043] substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
[1044] In the compound (the compound represented by General Formula (1000B) described above, the compound represented by General Formula (1000) described above, the compound represented by General Formula (1000A) described above, etc.) according to the present embodiment, R 901 and R902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 each independently is
[1045] a hydrogen atom,
[1046] substituted or unsubstituted alkyl having a carbon number of 1 to 50,
[1047] substituted or unsubstituted cycloalkyl having a ring-forming carbon number of 3 to 50,
[1048] substituted or unsubstituted aryl having a ring-forming carbon number of 6 to 50, or
[1049] substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50,
[1050] in the case where a plurality of R 901 exist, the plurality of R 901 are the same or different from each other,
[1051] in the case where a plurality of R 902 exist, the plurality of R 902 are the same or different from each other,
[1052] in the case where a plurality of R 903 exist, the plurality of R 903 are the same or different from each other,
[1053] in the case where a plurality of R 904 exist, the plurality of R 904 are the same or different from each other,
[1054] in the case where a plurality of R 905 exist, the plurality of R 905 are the same or different from each other,
[1055] in the case where a plurality of R 906 exist, the plurality of R 906 are the same or different from each other,
[1056] in the case where a plurality of R 907 exist, the plurality of R 907 are the same or different from each other,
[1057] in the case where a plurality of R 801 exist, the plurality of R 801 are the same or different from each other,
[1058] in the case where a plurality of R 802 exist, the plurality of R 802 are the same or different from each other.
[1059] The hydrogen atom in the compound according to the present embodiment is a protium atom, a deuterium atom, or a tritium atom. In one embodiment, the hydrogen atom in the compound according to the present embodiment is a protium atom. In one embodiment, the hydrogen atom in the compound according to the present embodiment is a deuterium atom.
[1060] • A method for producing the compound according to the present embodiment
[1061] The compound according to the present embodiment can be produced according to the synthetic methods described in the Examples below, or by imitating the synthetic methods using known alternative reactions and starting materials corresponding to the target substance.
[1062] • Specific examples of the compound according to the present embodiment
[1063] As specific examples of the compound according to the present embodiment, for example, the following compounds can be given. The present application is not limited to these specific examples. In the present specification, a deuterium atom is denoted as D and a protium atom is denoted as H or omitted from the description.
[1064] [Chemical Formula 52]
[1065]
[1066] [Chemical Formula 53]
[1067]
[1068] [Chemical Formula 54]
[1069]
[1070] [Chemical Formula 55]
[1071]
[1072] [Chemical Formula 56]
[1073]
[1074] [Chemical Formula 57]
[1075]
[1076] [Chemical Formula 58]
[1077]
[1078] [Chemical Formula 59]
[1079]
[1080] [Chemical Formula 60]
[1081]
[1082]
Chemical Formula 61
[1083]
[1084]
Chemical Formula 62
[1085]
[1086]
Chemical Formula 63
[1087]
[1088]
Chemical Formula 64
[1089]
[1090]
Chemical Formula 65
[1091]
[1092]
Chemical Formula 66
[1093]
[1094] [Chemical Formula 67]
[1095]
[1096]
Chemical Formula 68
[1097]
[1098]
Chemical Formula 69
[1099]
[1100] [Chemical Formula 70]
[1101]
[1102]
Chemical Formula 71
[1103]
[1104]
Chemical Formula 72
[1105]
[1106]
Chemical Formula 73
[1107]
[1108] [Chemical Formula 74]
[1109]
[1110] [Chemical Formula 75]
[1111]
[1112] [Chemical Formula 76]
[1113]
[1114] [Chemical Formula 77]
[1115]
[1116] [Chemical Formula 78]
[1117]
[1118] [Chemical Formula 79]
[1119]
[1120] [Chemical Formula 80]
[1121]
[1122] [Chemical Formula 81]
[1123]
[1124] [Chemical Formula 82]
[1125]
[1126] [Chemical Formula 83]
[1127]
[1128] [Chemical Formula 84]
[1129]
[1130] [Chemical Formula 85]
[1131]
[1132] [Chemical Formula 86]
[1133]
[1134] [Chemical Formula 87]
[1135]
[1136] [Chem. 88]
[1137]
[1138] [Chem. 89]
[1139]
[1140] [Chem. 90]
[1141]
[1142] [Chem. 91]
[1143]
[1144] [Chem. 92]
[1145]
[1146] [Chem. 93]
[1147]
[1148] [Chem. 94]
[1149]
[1150] [Chem. 95]
[1151]
[1152] [Chem. 96]
[1153]
[1154] [Chem. 97]
[1155]
[1156] [Chem. 98]
[1157]
[1158] [Chem. 99]
[1159]
[1160] [Chem. 100]
[1161]
[1162] [Chem. 101]
[1163]
[1164] [Chemical Formula 102]
[1165]
[1166] [Chemical Formula 103]
[1167]
[1168] [Chemical Formula 104]
[1169]
[1170] [Chemical Formula 105]
[1171]
[1172] [Chemical Formula 106]
[1173]
[1174] [Chemical Formula 107]
[1175]
[1176] [Chemical Formula 108]
[1177]
[1178] [Chemical Formula 109]
[1179]
[1180] [Chemical Formula 110]
[1181]
[1182] [Chemical Formula 111]
[1183]
[1184] [Chemical Formula 112]
[1185]
[1186] [Chemical Formula 113]
[1187]
[1188] [Chemical Formula 114]
[1189]
[1190] [Chemical Formula 115]
[1191]
[1192] [Chem. 116]
[1193]
[1194] [Chem. 117]
[1195]
[1196] [Chem. 118]
[1197]
[1198] [Chem. 119]
[1199]
[1200] [Chem. 120]
[1201]
[1202] [Chem. 121]
[1203]
[1204] [Chem. 122]
[1205]
[1206] [Chem. 123]
[1207]
[1208] [Chem. 124]
[1209]
[1210] [Chem. 125]
[1211]
[1212] [Chem. 126]
[1213]
[1214] [Chem. 127]
[1215]
[1216] [Chem. 128]
[1217]
[1218] [Chemical Formula 129]
[1219]
[1220] [Chemical Formula 130]
[1221]
[1222] [Chemical Formula 131]
[1223]
[1224] [Chemical Formula 132]
[1225]
[1226] [Chemical Formula 133]
[1227]
[1228] [Chemical Formula 134]
[1229]
[1230] [Chemical Formula 135]
[1231]
[1232] [Chemical Formula 136]
[1233]
[1234] [Chemical Formula 137]
[1235]
[1236] [Chemical Formula 138]
[1237]
[1238] [Chemical Formula 139]
[1239]
[1240] [Chemical Formula 140]
[1241]
[1242] [Chemical Formula 141]
[1243]
[1244] [Chemical Formula 142]
[1245]
[1246] [Chemical Formula 143]
[1247]
[1248] [Chemical Formula 144]
[1249]
[1250] [Chemical Formula 145]
[1251]
[1252] [Chemical Formula 146]
[1253]
[1254] [Chemical Formula 147]
[1255]
[1256] [Chemical Formula 148]
[1257]
[1258] [Chemical Formula 149]
[1259]
[1260] [Chemical Formula 150]
[1261]
[1262] [Chemical Formula 151]
[1263]
[1264] [Chemical Formula 152]
[1265]
[1266] [Chemical Formula 153]
[1267]
[1268] [Chemical Formula 154]
[1269]
[1270] [Chemical Formula 155]
[1271]
[1272] [Chemical Formula 156]
[1273]
[1274] [Chemical Formula 157]
[1275]
[1276] [Chemical Formula 158]
[1277]
[1278] [Chemical Formula 159]
[1279]
[1280] [Chemical Formula 160]
[1281]
[1282]
Chemical Formula 161
[1283]
[1284] [Chemical Formula 162]
[1285]
[1286] [Chemical Formula 163]
[1287]
[1288] [Chemical Formula 164]
[1289]
[1290] [Chemical Formula 165]
[1291]
[1292]
Chemical Formula 166
[1293]
[1294] [Chemical Formula 167]
[1295]
[1296] [Chemical Formula 168]
[1297]
[1298] [Chemical Formula 169]
[1299]
[1300] [Chemical Formula 170]
[1301]
[1302] [Chemical Formula 171]
[1303]
[1304] [Chemical Formula 172]
[1305]
[1306] [Chemical Formula 173]
[1307]
[1308] [Chemical Formula 174]
[1309]
[1310] [Chemical Formula 175]
[1311]
[1312] [Chemical Formula 176]
[1313]
[1314] [Chemical Formula 177]
[1315]
[1316] [Chemical Formula 178]
[1317]
[1318] [Chemical Formula 179]
[1319]
[1320] [Chemical Formula 180]
[1321]
[1322] [Chemical Formula 181]
[1323]
[1324] [Chemical Formula 182]
[1325]
[1326] [Chemical Formula 183]
[1327]
[1328] [Chemical Formula 184]
[1329]
[1330] [Chemical Formula 185]
[1331]
[1332] [Chemical Formula 186]
[1333]
[1334] [Chemical Formula 187]
[1335]
[1336] [Chemical Formula 188]
[1337]
[1338] [Chemical Formula 189]
[1339]
[1340] [Chemical Formula 190]
[1341]
[1342] [Chemical Formula 191]
[1343]
[1344] [Chemical Formula 192]
[1345]
[1346] [Chemical Formula 193]
[1347]
[1348] [Chemical Formula 194]
[1349]
[1350] [Chemical Formula 195]
[1351]
[1352] [Chemical Formula 196]
[1353]
[1354] [Chemical Formula 197]
[1355]
[1356] [Chemical Formula 198]
[1357]
[1358] [Chemical Formula 199]
[1359]
[1360] [Chemical Formula 200]
[1361]
[1362] [Chemical Formula 201]
[1363]
[1364] [Chemical Formula 202]
[1365]
[1366] [Chemical Formula 203]
[1367]
[1368] [Chemical Formula 204]
[1369]
[1370] [Chemical Formula 205]
[1371]
[1372] [Chemical Formula 206]
[1373]
[1374] [Chemical Formula 207]
[1375]
[1376] [Chemical Formula 208]
[1377]
[1378] [Chemical Formula 209]
[1379]
[1380] [Chemical Formula 210]
[1381]
[1382] [Chemical Formula 211]
[1383]
[1384] [Chemical Formula 212]
[1385]
[1386] [Chemical Formula 213]
[1387]
[1388] [Chemical Formula 214]
[1389]
[1390] [Chemical Formula 215]
[1391]
[1392] [Chemical Formula 216]
[1393]
[1394] [Chemical Formula 217]
[1395]
[1396] [Chemical Formula 218]
[1397]
[1398] [Chemical Formula 219]
[1399]
[1400] [Chemical Formula 220]
[1401]
[1402] [Chemical Formula 221]
[1403]
[1404] [Chemical Formula 222]
[1405]
[1406] [Chemical Formula 223]
[1407]
[1408] [Chemical Formula 224]
[1409]
[1410] [Chemical Formula 225]
[1411]
[1412] [Chemical Formula 226]
[1413]
[1414] [Chemical Formula 227]
[1415]
[1416] [Chemical Formula 228]
[1417]
[1418] [Chemical Formula 229]
[1419]
[1420] [Chemical Formula 230]
[1421]
[1422] [Chemical Formula 231]
[1423]
[1424] [Chemical Formula 232]
[1425]
[1426] [Chemical Formula 233]
[1427]
[1428] [Chemical Formula 234]
[1429]
[1430] [Chemical Formula 235]
[1431]
[1432] [Chemical Formula 236]
[1433]
[1434] [Chemical Formula 237]
[1435]
[1436] [Chemical Formula 238]
[1437]
[1438] [Chem. 239]
[1439]
[1440] [Chem. 240]
[1441]
[1442] [Chem. 241]
[1443]
[1444] [Chem. 242]
[1445]
[1446] [Chem. 243]
[1447]
[1448] [Chem. 244]
[1449]
[1450] [Chem. 245]
[1451]
[1452] [Chem. 246]
[1453]
[1454] [Chem. 247]
[1455]
[1456] [Chem. 248]
[1457]
[1458] [Chem. 249]
[1459]
[1460] [Chem. 250]
[1461]
[1462] [Chem. 251]
[1463]
[1464] [Chemical Formula 252]
[1465]
[1466] [Chemical Formula 253]
[1467]
[1468] [Chemical Formula 254]
[1469]
[1470] [Chemical Formula 255]
[1471]
[1472] [Chemical Formula 256]
[1473]
[1474] [Chemical Formula 257]
[1475]
[1476] [Chemical Formula 258]
[1477]
[1478] [Chemical Formula 259]
[1479]
[1480] [Chemical Formula 260]
[1481]
[1482] [Chemical Formula 261]
[1483]
[1484] [Chemical Formula 262]
[1485]
[1486] [Chemical Formula 263]
[1487]
[1488] [Chemical Formula 264]
[1489]
[1490] [Chemical Formula 265]
[1491]
[1492] [Chem. 266]
[1493]
[1494] [Chem. 267]
[1495]
[1496] [Chem. 268]
[1497]
[1498] [Chem. 269]
[1499]
[1500] [Chem. 270]
[1501]
[1502] [Chem. 271]
[1503]
[1504] [Chem. 272]
[1505]
[1506] [Chem. 273]
[1507]
[1508] [Chem. 274]
[1509]
[1510] [Chem. 275]
[1511]
[1512] [Chem. 276]
[1513]
[1514] [Chem. 277]
[1515]
[1516] [Chem. 278]
[1517]
[1518] [Chem. 279]
[1519]
[1520]
Chemical Formula 280
[1521]
[1522] According to the compound according to the present embodiment, the performance of an organic EL element can be improved. In addition, when the compound according to the present embodiment is used for a light-emitting layer (first light-emitting layer) on the anode side of an organic EL element in which a plurality of light-emitting layers are stacked, an element with good balance between luminous efficiency and lifetime can be provided.
[1523] [Second Embodiment]
[1524] (Material for Organic Electroluminescence Element)
[1525] The material for an organic electroluminescence element according to the present embodiment contains the compound according to the first embodiment. As one aspect, a material for an organic electroluminescence element containing only the compound according to the first embodiment can be given, and as another aspect, a material for an organic electroluminescence element containing the compound according to the first embodiment and another compound different from the compound according to the first embodiment can be given.
[1526] In the material for an organic electroluminescence element according to the present embodiment, the compound according to the first embodiment is preferably a host material. In this case, the material for an organic electroluminescence element can contain the compound according to the first embodiment as a host material and another compound such as a dopant material.
[1527] [Third Embodiment]
[1528] [Organic Electroluminescence Element]
[1529] An organic EL element according to the present embodiment will be described.
[1530] The organic EL element according to the present embodiment has an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer contains at least one layer composed of an organic compound. Alternatively, the organic layer is composed of a plurality of layers composed of organic compounds stacked. The organic layer can further contain an inorganic compound.
[1531] In the organic EL element according to the present embodiment, at least one layer of the organic layer contains the compound according to the first embodiment.
[1532] In the organic EL element of the present embodiment, at least one of the organic layers is preferably a light-emitting layer. In the organic EL element of the present embodiment, the light-emitting layer preferably contains the compound according to the first embodiment. In one embodiment, the light-emitting layer contains the compound represented by the above general formula (100). In one embodiment, the light-emitting layer contains the compound represented by the above general formula (1). In one embodiment, the light-emitting layer contains the compound represented by the above general formula (100A).
[1533] In one embodiment, the light-emitting layer can also contain a metal complex.
[1534] In addition, in one embodiment, the light-emitting layer preferably does not contain a metal complex.
[1535] In addition, in one embodiment, the light-emitting layer preferably does not contain a phosphorescent light-emitting material (dopant material).
[1536] In addition, in one embodiment, the light-emitting layer preferably does not contain a heavy metal complex and a phosphorescent light-emitting rare earth metal complex. As the heavy metal complex, for example, there can be mentioned iridium complexes, osmium complexes, platinum complexes, and the like.
[1537] The organic layer can be composed of one light-emitting layer, or can contain a layer that is useful for an organic EL element. As the layer that is useful for an organic EL element, there is no particular limitation, and for example, there can be mentioned at least any one layer selected from the group consisting of a hole-injection layer, a hole-transport layer, an electron-injection layer, an electron-transport layer, and a blocking layer.
[1538] The organic EL element according to the present embodiment preferably has a hole-transport layer between the anode and the light-emitting layer.
[1539] The organic EL element according to the present embodiment preferably has an electron-transport layer between the cathode and the light-emitting layer.
[1540] In the organic EL element according to the present embodiment, the organic layer can be composed of a plurality of light-emitting layers. For example, the organic layer can be composed of two light-emitting layers of a first light-emitting layer and a second light-emitting layer. The organic EL element according to the present embodiment can have one or more organic layers other than the first light-emitting layer and the second light-emitting layer, and can further have at least any one layer selected from the group consisting of, for example, a hole-injection layer, a hole-transport layer, an electron-injection layer, an electron-transport layer, a hole-blocking layer, an electron-blocking layer, and the like.
[1541] In the organic EL element according to the present embodiment, the organic layer preferably has a first light-emitting layer and a second light-emitting layer.
[1542] As one scheme, a case is assumed in which the first light-emitting layer is provided between the anode and the cathode, and the second light-emitting layer is provided between the first light-emitting layer and the cathode. In addition, as another scheme, a case is assumed in which the second light-emitting layer is provided between the anode and the cathode, and the first light-emitting layer is provided between the second light-emitting layer and the cathode. In the organic EL element according to the present embodiment, the first light-emitting layer and the second light-emitting layer can be provided in accordance with any of the above schemes.
[1543] In the organic EL element according to the present embodiment, the first light-emitting layer and the second light-emitting layer can be in direct contact with each other or can not be in direct contact with each other.
[1544] An organic EL element according to one embodiment has an anode, a cathode, a first light-emitting layer provided between the anode and the cathode, and a second light-emitting layer provided between the first light-emitting layer and the cathode, the first light-emitting layer contains a first compound, the first compound is a compound represented by the above general formula (100) having at least one group represented by the above general formula (110), and the first light-emitting layer is in direct contact with the second light-emitting layer.
[1545] In the organic EL element according to the present embodiment, in a case where the organic layer has a light-emitting layer, it is preferable that an electron-transporting layer be provided between the cathode and the light-emitting layer. In a case where the light-emitting layer has a first light-emitting layer and a second light-emitting layer, in one scheme, an electron-transporting layer can also be provided between the cathode and the second light-emitting layer.
[1546] In the organic EL element according to the present embodiment, in a case where the organic layer has a light-emitting layer, it is preferable that a hole-transporting layer be provided between the anode and the light-emitting layer. In a case where the light-emitting layer has a first light-emitting layer and a second light-emitting layer, in one scheme, a hole-transporting layer can also be provided between the anode and the first light-emitting layer.
[1547] In the organic EL element according to the present embodiment, a non-doped region which does not contain a third compound having a fluorescent light-emitting property can be provided on the anode side of the first light-emitting layer.
[1548] In addition, the organic EL element according to the present embodiment can contain a first light-emitting layer, a second light-emitting layer, and a non-doped region provided between the anode and the first light-emitting layer. The non-doped region can be, for example, a non-doped organic layer which is in direct contact with the anode side of the first light-emitting layer.
[1549] The non-doped organic layer does not contain a metal atom, and the content of each of all the materials constituting the non-doped organic layer is preferably 10% by mass or more, more preferably exceeds 10% by mass. The non-doped organic layer preferably contains the compound according to the first embodiment. The non-doped organic layer is preferably composed only of the compound according to the first embodiment.
[1550] The non-doped organic layer is, for example, a second hole-transporting layer or an electron-blocking layer.
[1551] Figure 1 A schematic configuration of an example of an organic EL element to which the present embodiment is applied is shown.
[1552] 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 configured by sequentially stacking, in this order, a hole-injecting layer 6, a hole-transporting layer 7, a first light-emitting layer 51, a second light-emitting layer 52, an electron-transporting layer 8, and an electron-injecting layer 9 from the anode 3 side.
[1553] (First light-emitting layer)
[1554] In the organic EL element to which the present embodiment is applied, the first light-emitting layer preferably contains a first compound. The first compound is preferably a first host material.
[1555] In the organic EL element to which the present embodiment is applied, the first light-emitting layer also preferably contains a third compound having fluorescent light-emitting properties. The first light-emitting layer also preferably contains the first compound as a first host material and the third compound as a first dopant material.
[1556] In the present specification, a "host material" refers to a material having a content of, for example, "50% by mass or more of the layer". Thus, for example, in the first light-emitting layer, the content of the first compound is 50% by mass or more of the total mass of the first light-emitting layer. In addition, for example, the content of the "host material" can be 60% by mass or more of the layer, 70% by mass or more of the layer, 80% by mass or more of the layer, 90% by mass or more of the layer, or 95% by mass or more of the layer.
[1557] (First compound)
[1558] In the organic EL element to which the present embodiment is applied, the first compound is a compound to which the first embodiment is applied.
[1559] In the organic EL element to which one embodiment is applied, the first compound is a compound represented by the above general formula (1000B) having at least one group represented by the above general formula (110).
[1560] In the organic EL element to which one embodiment is applied, the first compound is a compound having at least one group represented by the above general formula (11) and containing only one benzo[de]anthracene derivative skeleton represented by the above general formula (1000) in a molecule.
[1561] In the organic EL element according to one embodiment, the first compound is a compound having at least one group represented by the above general formula (110A) and containing only one benz[de]anthracene derivative skeleton represented by the above general formula (1000A) in a molecule.
[1562] (the second light-emitting layer)
[1563] In the organic EL element according to one embodiment, the second light-emitting layer preferably contains a second compound. The second compound is preferably a second host material.
[1564] In the organic EL element according to one embodiment, the second light-emitting layer preferably contains a fourth compound having a fluorescent light-emitting property. The second light-emitting layer preferably contains the second compound as a second host material and the fourth compound as a second dopant material.
[1565] In the case where the first light-emitting layer contains a third compound and the second light-emitting layer contains a fourth compound, the third compound and the fourth compound are the same or different from each other.
[1566] (the second compound)
[1567] In the organic EL element according to one embodiment, the second compound is not particularly limited. In the organic EL element according to one embodiment, the second compound as a host material can be, for example, a heterocyclic compound, a fused aromatic compound, or the like. As the fused aromatic compound, for example, an anthracene derivative, a pyrene derivative, a benzanthracene derivative, or the like can be given.
[1568] The second compound is preferably, for example, a compound represented by the above general formula (2).
[1569] [Chemical Formula 281]
[1570]
[1571] (in the above general formula (2),
[1572] R 201 ~R 208 each independently is
[1573] a hydrogen atom,
[1574] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[1575] a substituted or unsubstituted haloalkyl group having a carbon number of 1 to 50,
[1576] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[1577] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,
[1578] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
[1579] a group represented by -Si(R 901 )(R 902 )(R 903 ),
[1580] a group represented by -O-(R 904 ),
[1581] a group represented by -S-(R 905 ),
[1582] a group represented by -N(R 906 )(R 907 ),
[1583] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,
[1584] a group represented by -C(=O)R 801 ,
[1585] a group represented by -COOR 802 ,
[1586] a halogen atom,
[1587] a nitro group,
[1588] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or
[1589] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,
[1590] L 201 and L 202 are each independently
[1591] a single bond,
[1592] a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or
[1593] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms,
[1594] Ar 201 and Ar 202 are each independently
[1595] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or
[1596] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
[1597] (in the second compound according to the present embodiment, R 901 , R 902 , R 903, R 904 , R 905 , R 906 , R 907 , R 801 and R 802 are each independently
[1598] a hydrogen atom,
[1599] substituted or unsubstituted alkyl of carbon number 1 to 50,
[1600] substituted or unsubstituted cycloalkyl of ring-forming carbon number 3 to 50,
[1601] substituted or unsubstituted aryl of ring-forming carbon number 6 to 50, or
[1602] substituted or unsubstituted heterocyclic group of ring-forming atom number 5 to 50,
[1603] in the case where a plurality of R 901 exist, the plurality of R 901 are the same or different from each other,
[1604] in the case where a plurality of R 902 exist, the plurality of R 902 are the same or different from each other,
[1605] in the case where a plurality of R 903 exist, the plurality of R 903 are the same or different from each other,
[1606] in the case where a plurality of R 904 exist, the plurality of R 904 are the same or different from each other,
[1607] in the case where a plurality of R 905 exist, the plurality of R 905 are the same or different from each other,
[1608] in the case where a plurality of R 906 exist, the plurality of R 906 are the same or different from each other,
[1609] in the case where a plurality of R 907 exist, the plurality of R 907 are the same or different from each other,
[1610] in the case where a plurality of R 801 exist, the plurality of R 801 are the same or different from each other,
[1611] in the case where a plurality of R 802 exist, the plurality of R 802 are the same or different from each other.
[1612] In the organic EL element according to the present embodiment, it is preferable that R 201 ~R 208 each independently be
[1613] a hydrogen atom,
[1614] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[1615] a substituted or unsubstituted haloalkyl group having a carbon number of 1 to 50,
[1616] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[1617] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,
[1618] a substituted or unsubstituted cyclic alkyl group having a ring-forming carbon number of 3 to 50,
[1619] a group represented by -Si(R 901 )(R 902 )(R 903 ),
[1620] a group represented by -O-(R 904 ),
[1621] a group represented by -S-(R 905 ),
[1622] a group represented by -N(R 906 )(R 907 ),
[1623] a substituted or unsubstituted aralkyl group having a carbon number of 7 to 50,
[1624] a group represented by -C(=O)R 801 ,
[1625] a group represented by -COOR 802 ,
[1626] a halogen atom, or
[1627] a nitro group,
[1628] L 201 and L 202 each independently be
[1629] a single bond,
[1630] a substituted or unsubstituted arylene group having a ring-forming carbon number of 6 to 50, or
[1631] a substituted or unsubstituted divalent heterocyclic group having a ring-forming atom number of 5 to 50,
[1632] Ar 201 and Ar202 each independently is
[1633] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or
[1634] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
[1635] R 201 ~R 208 each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, or a group represented by -Si(R 901 )(R 902 )(R 903 ).
[1636] R 201 ~R 208 is also preferably a hydrogen atom.
[1637] In the organic EL element according to the present embodiment, it is preferable that L 201 and L 202 each independently is a single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, Ar 201 and Ar 202 each independently is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.
[1638] In the organic EL element according to the present embodiment, it is preferable that Ar 201 and Ar 202 each independently is
[1639] a phenyl group,
[1640] a naphthyl group,
[1641] a phenanthryl group,
[1642] a biphenyl group,
[1643] a terphenyl group,
[1644] a diphenylfluorenyl group,
[1645] a dimethylfluorenyl group,
[1646] a benzdiphenylfluorenyl group,
[1647] a benzdimehtylfluorenyl group,
[1648] a dibenzofuranyl group,
[1649] a dibenzothiophenyl group,
[1650] a benzoxanthlenyl group,
[1651] naphthobenzofuranyl group, or
[1652] naphthobenzothiophenyl group.
[1653] In the organic EL element according to the present embodiment, it is preferable that the second compound represented by the above general formula (2) be a compound represented by the following general formula (201), general formula (202), general formula (203), general formula (204), general formula (205), general formula (206), general formula (207), general formula (208), or general formula (209).
[1654] [Chemical Formula 282]
[1655]
[1656] [Chemical Formula 283]
[1657]
[1658] [Chemical Formula 284]
[1659]
[1660] [Chemical Formula 285]
[1661]
[1662] [Chemical Formula 286]
[1663]
[1664] [Chemical Formula 287]
[1665]
[1666] [Chemical Formula 288]
[1667]
[1668] [Chemical Formula 289]
[1669]
[1670] [Chemical Formula 290]
[1671]
[1672] (In the above general formulae (201) to (209), L 201 and Ar 201 have the same meanings as L 201 and Ar 201 in the above general formula (2), and R 201 ~R208 each independently R in the above general formula (2) 201 ~R 208 have the same meaning.
[1673] The second compound represented by the above general formula (2) is also preferably a compound represented by the following general formula (221), general formula (222), general formula (223), general formula (224), general formula (225), general formula (226), general formula (227), general formula (228), or general formula (229).
[1674] [Chemical Formula 291]
[1675]
[1676] [Chemical Formula 292]
[1677]
[1678] [Chemical Formula 293]
[1679]
[1680] [Chemical Formula 294]
[1681]
[1682] [Chemical Formula 295]
[1683]
[1684] [Chemical Formula 296]
[1685]
[1686] [Chemical Formula 297]
[1687]
[1688] [Chemical Formula 298]
[1689]
[1690] [Chemical Formula 299]
[1691]
[1692] (in the above general formula (221), general formula (222), general formula (223), general formula (224), general formula (225), general formula (226), general formula (227), general formula (228), and general formula (229),
[1693] R 201 and R 203~R 208 Each independently relates to R in the above general formula (2) 201 and R 203 ~R 208 Same meaning
[1694] L 201 and Ar 201 Each of them corresponds to L in the above general formula (2) 201 and Ar 201 Same meaning
[1695] L 203 L in the above general formula (2) 201 Same meaning
[1696] L 203 With L 201 They are the same or different.
[1697] Ar 203 Ar in the above general formula (2) 201 Same meaning
[1698] Ar 203 with Ar 201 (They may be the same or different.)
[1699] 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).
[1700]
Chemical Formula 300
[1701]
[1702]
Chemical Formula 301
[1703]
[1704]
Chemical Formula 302
[1705]
[1706]
Chemical Formula 303
[1707]
[1708] Chemical formula 304
[1709]
[1710]
Chemical Formula 305
[1711]
[1712]
Chemical Formula 306
[1713]
[1714]
Chemical Formula 307
[1715]
[1716] [Chemical Formula 308]
[1717]
[1718] (In the above general formulas (241), (242), (243), (244), (245), (246), (247), (248), and (249),
[1719] 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
[1720] L 201 and Ar 201 Each of the above general formulas (2) with L 201 and Ar 201 Same meaning
[1721] L 203 L in the above general formula (2) 201 Same meaning
[1722] L 203 With L 201 They are the same or different.
[1723] Ar 203 Ar in the above general formula (2) 201 Same meaning
[1724] Ar 203 with Ar 201 (They may be the same or different.)
[1725] In the second compound represented by the above general formula (2), R is preferred. 201 ~R 208 Each independently
[1726] hydrogen atom,
[1727] substituted or unsubstituted alkyl group having a carbon atom number of 1 to 50,
[1728] substituted or unsubstituted cyclic alkyl group having a ring-forming carbon atom number of 3 to 50, or
[1729] -Si(R 901 )(R 902 )(R 903 ) group.
[1730] Preferably, L 101 is
[1731] a single bond, or
[1732] unsubstituted arylene group having a ring-forming carbon atom number of 6 to 22,
[1733] Ar 101 is a substituted or unsubstituted aryl group having a ring-forming carbon atom number of 6 to 22.
[1734] In the organic EL element according to the present embodiment, in the second compound represented by General Formula (2) above, from the viewpoint of preventing the intermolecular interaction from being inhibited and the electron mobility from being inhibited from decreasing, R 201 to R 208 are preferably hydrogen atoms, but R 201 to R 208 may be a substituted or unsubstituted aryl group having a ring-forming carbon atom number of 6 to 50, or a substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50.
[1735] In the case where R 201 to R 208 are bulky substituents such as alkyl groups and cyclic alkyl groups, the intermolecular interaction is inhibited, the electron mobility decreases relative to the first compound, and it can be possible that the relationship μH2> μH1 described in the following Mathematical Formula (Mathematical Formula 3) is not satisfied. In the case where the second compound is used for the second light-emitting layer, by satisfying the relationship μH2> μH1, it is possible to expect that the decrease in the recombination ability of holes and electrons in the first light-emitting layer and the decrease in the light-emitting efficiency are inhibited. Note that, as the substituents, halogenalkyl groups, alkenyl groups, alkynyl groups, -Si(R 901 )(R 902 )(R 903 ) groups, -O-(R 904 ) groups, -S-(R 905 ) groups, -N(R 906 )(R 907 ) groups, aralkyl groups, -C(=O)R 801 groups, -COOR 802 groups, and the like are not preferable.The groups, halogen atoms, cyano groups, and nitro groups shown may be large in size, while alkyl and cycloalkyl groups may be even larger.
[1736] In the second compound represented by the above general formula (2), R, as a substituent of the anthracene skeleton, 201 ~R 208 Preferably, the substituents are not bulky; preferably, they are not alkyl or cycloalkyl; more preferably, they are not alkyl, cycloalkyl, haloalkyl, alkenyl, alkynyl, or -Si(R) substituents. 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 are halogen atoms, cyano groups, and nitro groups.
[1737] In the organic EL element involved in this embodiment, R is also preferred in the second compound shown in the above general formula (2). 201 ~R 208 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, or a -Si(R) group. 901 (R) 902 (R) 903 The group shown is ).
[1738] In the organic EL element of this embodiment, in the second compound represented by the above general formula (2), R 201 ~R 208 Hydrogen atoms are preferred.
[1739] 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 aforementioned potentially bulky substituents, especially substituted or unsubstituted alkyl groups and substituted or unsubstituted cycloalkyl groups. R 201 ~R 208 When the substituent is described as "substituted or unsubstituted", it can prevent the suppression of intermolecular interactions caused by the presence of bulky substituents such as alkyl and cycloalkyl groups by not containing substituted or unsubstituted alkyl and substituted or unsubstituted cycloalkyl groups, thus preventing a 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.
[1740] Further preferably, R as a substituent of the anthracene skeleton is not a bulky substituent. 201 ~R 208 Further preferably, R as a substituent of the anthracene skeleton is not a bulky substituent. 201 ~R 208 is not a bulky substituent. In addition, R as a substituent of the anthracene skeleton is not a bulky substituent. 201 ~R 208 is not a bulky substituent. In addition, R as a substituent of the anthracene skeleton is not a bulky substituent. 201 ~R 208 is not a bulky substituent. In addition, R as a substituent of the anthracene skeleton is not a bulky substituent. 201 ~R 208 is not a bulky substituent. In addition, R as a substituent of the anthracene skeleton is not a bulky substituent. 901 is not a bulky substituent. In addition, R as a substituent of the anthracene skeleton is not a bulky substituent. 902 is not a bulky substituent. In addition, R as a substituent of the anthracene skeleton is not a bulky substituent. 903 is not a bulky substituent. In addition, R as a substituent of the anthracene skeleton is not a bulky substituent. 904 is not a bulky substituent. In addition, R as a substituent of the anthracene skeleton is not a bulky substituent. 905 is not a bulky substituent. In addition, R as a substituent of the anthracene skeleton is not a bulky substituent. 906) is not a bulky substituent. In addition, R as a substituent of the anthracene skeleton is not a bulky substituent. 907 is not a bulky substituent. In addition, R as a substituent of the anthracene skeleton is not a bulky substituent. 801 is not a bulky substituent. In addition, R as a substituent of the anthracene skeleton is not a bulky substituent. 802 is not a bulky substituent. In addition, R as a substituent of the anthracene skeleton is not a bulky substituent.
[1741] In the first compound and the second compound, it is also preferable that the group described as "substituted or unsubstituted" be an "unsubstituted" group.
[1742] In the organic EL element according to the present embodiment, Ar 201 in the second compound represented by General Formula (2) described above is a substituted or unsubstituted dibenzofuranyl group.
[1743] In the organic EL element according to the present embodiment, Ar 201 in the second compound represented by General Formula (2) described above is an unsubstituted dibenzofuranyl group.
[1744] In the organic EL element according to the present embodiment, at least one of the hydrogens in the second compound represented by General Formula (2) described above is deuterium.
[1745] In the organic EL element according to the present embodiment, L 201 in the second compound represented by General Formula (2) described above is TEMP-63 to TEMP-68.
[1746]
Chemical Formula 309
[1747]
[1748] In General Formulae (TEMP-63) to (TEMP-68) above, * indicates a bonding position.
[1749] In the organic EL element according to the present embodiment, Ar 201 is at least one selected from the group consisting of a substituted or unsubstituted anthracenyl group,
[1750] a benzanthracenyl group,
[1751] a phenanthrenyl group,
[1752] a benzophenanthrenyl group,
[1753] an indenyl group,
[1754] a pyrenyl group,
[1755] a chrysenyl group,
[1756] a benzochrysenyl group, a triphenylenyl group,
[1757] a benzenetriphenylenyl group,
[1758] a tetracenyl group,
[1759] a naphthacene group,
[1760] a pentacenyl group,
[1761] a fluoranthenyl group,
[1762] a benzofluoranthenyl group, and
[1763] a perylenyl group.
[1764] In the organic EL element according to the present embodiment, Ar 201 is a substituted or unsubstituted fluorenyl group.
[1765] In the organic EL element according to the present embodiment, Ar 201 is a substituted or unsubstituted xanthenyl group.
[1766] In the organic EL element according to the present embodiment, Ar 201 is a benzoxanthenyl group.
[1767] (Method for producing second compound)
[1768] The second compound can be produced by a publicly known method. In addition, the second compound can also be produced by imitating the publicly known method, using a known alternative reaction and starting material corresponding to the target substance.
[1769] (Specific examples of the second compound)
[1770] As specific examples of the second compound, for example, the following compounds can be given. Among them, the present application is not limited to these specific examples of the second compound.
[1771] [Chemical Formula 310]
[1772]
[1773] [Chemical Formula 311]
[1774]
[1775] [Chemical Formula 312]
[1776]
[1777] [Chemical Formula 313]
[1778]
[1779] [Chemical Formula 314]
[1780]
[1781] [Chemical Formula 315]
[1782]
[1783] [Chemical Formula 316]
[1784]
[1785] [Chemical Formula 317]
[1786]
[1787] [Chemical Formula 318]
[1788]
[1789] [Chemical Formula 319]
[1790]
[1791] [Chemical Formula 320]
[1792]
[1793] [Chemical Formula 321]
[1794]
[1795] [Chemical Formula 322]
[1796]
[1797] [Chemical Formula 323]
[1798]
[1799] [Chemical Formula 324]
[1800]
[1801] [Chemical Formula 325]
[1802]
[1803] [Chemical Formula 326]
[1804]
[1805] [Chemical Formula 327]
[1806]
[1807] [Chemical Formula 328]
[1808]
[1809] [Chemical Formula 329]
[1810]
[1811] [Chemical Formula 330]
[1812]
[1813] [Chemical Formula 331]
[1814]
[1815] [Chemical Formula 332]
[1816]
[1817] [Chemical Formula 333]
[1818]
[1819] [Chemical Formula 334]
[1820]
[1821] [Chem. 335]
[1822]
[1823] [Chem. 336]
[1824]
[1825] [Chem. 337]
[1826]
[1827] [Chem. 338]
[1828]
[1829] [Chem. 339]
[1830]
[1831] [Chem. 340]
[1832]
[1833] [Chem. 341]
[1834]
[1835] [Chem. 342]
[1836]
[1837] [Chem. 343]
[1838]
[1839] [Chem. 344]
[1840]
[1841] [Chem. 345]
[1842]
[1843] [Chem. 346]
[1844]
[1845] [Chem. 347]
[1846]
[1847] [Chem. 348]
[1848]
[1849] [Chemical Formula 349]
[1850]
[1851] [Chemical Formula 350]
[1852]
[1853] [Chemical Formula 351]
[1854]
[1855] [Chemical Formula 352]
[1856]
[1857] (third compound and fourth compound)
[1858] The third compound and the fourth compound are each independently one or more compounds selected from the group consisting of a compound represented by General Formula (3) below, a compound represented by General Formula (4) below, a compound represented by General Formula (5) below, a compound represented by General Formula (6) below, a compound represented by General Formula (7) below, a compound represented by General Formula (8) below, a compound represented by General Formula (9) below, and a compound represented by General Formula (10) below.
[1859] (compound represented by General Formula (3))
[1860] The compound represented by General Formula (3) is described.
[1861] [Chemical Formula 353]
[1862]
[1863] (in General Formula (3) above,
[1864] R 301 R 310 one or more groups consisting of 2 or more adjacent groups selected from the group consisting of R
[1865] are bonded to each other to form a substituted or unsubstituted monocyclic ring,
[1866] are bonded to each other to form a substituted or unsubstituted fused ring, or
[1867] are not bonded to each other,
[1868] R 301 R 310at least one of which is a monovalent group represented by the following general formula (31),
[1869] R which is not a monovalent group represented by the following general formula (31) 301 ~R 310 each independently is
[1870] a hydrogen atom,
[1871] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[1872] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[1873] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,
[1874] a substituted or unsubstituted cyclic alkyl group having a ring-forming carbon number of 3 to 50,
[1875] a group represented by the following general formula (R 901 )(R 902 )(R 903 ),
[1876] a group represented by the following general formula (R 904 ),
[1877] a group represented by the following general formula (R 905 ),
[1878] a group represented by the following general formula (R 906 )(R 907 ),
[1879] a halogen atom,
[1880] a cyano group,
[1881] a nitro group,
[1882] a substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50, or
[1883] a substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50.
[1884] [Chemical Formula 354]
[1885]
[1886] (in the above general formula (31),
[1887] Ar 301 and Ar 302 each independently is
[1888] a substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50, or
[1889] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1890] L 301 ~L 303 Each independently
[1891] single bond,
[1892] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or
[1893] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.
[1894] * indicates the bonding position in the pyrene ring in the above general formula (3).
[1895] In the third and fourth compounds, R 901 R 902 R 903 R 904 R 905 R 906 and R 907 Each independently
[1896] hydrogen atom,
[1897] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1898] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1899] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1900] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1901] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[1902] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[1903] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.
[1904] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
[1905] In R 905 In the case of multiple Rs, multiple Rs905 They are the same or different.
[1906] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.
[1907] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.
[1908] In the above general formula (3), R is preferred. 301 ~R 310 Two of them are groups represented by the general formula (31) above.
[1909] In one embodiment, the compound represented by the above general formula (3) is the compound represented by the following general formula (33).
[1910]
Chemical Formula 355
[1911]
[1912] (In the above general formula (33),
[1913] 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
[1914] L 311 ~L 316 Each independently
[1915] single bond,
[1916] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or
[1917] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.
[1918] Ar 312 Ar 313 Ar 315 and Ar 316 Each independently
[1919] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1920] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[1921] In the above general formula (31), L 301 Preferably a single bond, L 302 and L303 preferably a single bond.
[1922] In one embodiment, the compound represented by General Formula (3) described above is represented by General Formula (34) or General Formula (35) described below.
[1923] [Chemical Formula 356]
[1924]
[1925] (in General Formula (34) described above,
[1926] R 311 ~R 318 each independently has the same meaning as R in General Formula (3) described above except for the monovalent group represented by General Formula (31) described above. 301 ~R 310 each independently has the same meaning as R in General Formula (3) described above except for the monovalent group represented by General Formula (31) described above.
[1927] L 312 , L 313 , L 315 , and L 316 each independently has the same meaning as L in General Formula (33) described above. 312 , L 313 , L 315 , and L 316 each independently has the same meaning as L in General Formula (33) described above.
[1928] Ar 312 , Ar 313 , Ar 315 , and Ar 316 each independently has the same meaning as Ar in General Formula (33) described above. 312 , Ar 313 , Ar 315 , and Ar 316 each independently has the same meaning as Ar in General Formula (33) described above.
[1929] [Chemical Formula 356]
[1930]
[1931] (in General Formula (35) described above,
[1932] R 311 ~R 318 each independently has the same meaning as R in General Formula (3) described above except for the monovalent group represented by General Formula (31) described above. 301 ~R 310 each independently has the same meaning as R in General Formula (3) described above except for the monovalent group represented by General Formula (31) described above.
[1933] Ar 312 , Ar 313 , Ar 315 , and Ar 316 each independently has the same meaning as Ar in General Formula (33) described above.312 Ar 313 Ar 315 and Ar 316 The meaning is the same.
[1934] In the above general formula (31), Ar is preferred. 301 and Ar 302 At least one of them is a group represented by the following general formula (36).
[1935] 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).
[1936] 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).
[1937] [Chemical Formula 358]
[1938]
[1939] (In the above general formula (36),
[1940] X3 represents an oxygen atom or a sulfur atom.
[1941] By R 321 ~R 327 One or more groups consisting of two or more adjacent elements.
[1942] They bond together to form substituted or unsubstituted monocyclic rings.
[1943] They bond together to form substituted or unsubstituted fused rings, or
[1944] They are not mutually bonded.
[1945] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 321 ~R 327 Each independently
[1946] hydrogen atom,
[1947] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1948] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1949] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1950] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1951] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1952] -O-(R 904 The groups shown in the figure,
[1953] -S-(R 905 The groups shown in the figure,
[1954] -N(R 906 (R) 907 The groups shown in the figure,
[1955] Halogen atoms,
[1956] cyano,
[1957] Nitro,
[1958] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1959] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1960] * indicates that L 302 L 303 L 312 L 313 L 315 or L 316 (The bonding location.)
[1961] X3 is preferably an oxygen atom.
[1962] Preferably, R 321 ~R 327 At least one of them is
[1963] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1964] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1965] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1966] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1967] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1968] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1969] In the above general formula (31), it is preferred that Ar 301Ar is a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms. 302 Ar is a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms.
[1970] Ar is a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms. 312 Ar is a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms. 313 Ar is a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms.
[1971] Ar is a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms. 315 Ar is a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms. 316 Ar is a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms.
[1972] In one embodiment, the compound represented by General Formula (3) is represented by General Formula (37).
[1973]
Chemical Formula 359
[1974]
[1975] (in General Formula (37) above,
[1976] R 311 R 318 each independently R 301 R 310 have the same meaning as in General Formula (3) above,
[1977] R 321 R 327 one or more groups consisting of 2 or more adjacent ones of R
[1978] are bonded to each other to form a substituted or unsubstituted monocyclic,
[1979] are bonded to each other to form a substituted or unsubstituted fused ring, or
[1980] are not bonded to each other,
[1981] R 341 R 347 one or more groups consisting of 2 or more adjacent ones of R
[1982] are bonded to each other to form a substituted or unsubstituted monocyclic,
[1983] are bonded to each other to form a substituted or unsubstituted fused ring, or
[1984] are not bonded to each other,
[1985] R 321 ~R 327 and R 341 ~R 347 each independently is
[1986] a hydrogen atom,
[1987] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[1988] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[1989] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,
[1990] a substituted or unsubstituted cycloalkyl group having a ring-constituting carbon number of 3 to 50,
[1991] a group represented by -Si(R 901 )(R 902 )(R 903 ),
[1992] a group represented by -O-(R 904 ),
[1993] a group represented by -S-(R 905 ),
[1994] a group represented by -N(R 906 )(R 907 ),
[1995] a halogen atom,
[1996] a cyano group,
[1997] a nitro group,
[1998] a substituted or unsubstituted aryl group having a ring-constituting carbon number of 6 to 50, or
[1999] a substituted or unsubstituted heterocyclic group having a ring-constituting atom number of 5 to 50,
[2000] R 331 ~R 335 and R 351 ~R 355 each independently is
[2001] a hydrogen atom,
[2002] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[2003] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[2004] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,
[2005] substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
[2006] -Si(R 901 )(R 902 )(R 903 ) group,
[2007] -O-(R 904 ) group,
[2008] -S-(R 905 ) group,
[2009] -N(R 906 )(R 907 ) group,
[2010] a halogen atom, a cyano group, a nitro group,
[2011] substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or
[2012] substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
[2013] As the compound represented by the above general formula (3), for example, the following compounds represented by the following general formulae can be given as specific examples.
[2014] [Chemical Formula 360]
[2015]
[2016] [Chemical Formula 361]
[2017]
[2018] [Chemical Formula 362]
[2019]
[2020] [Chemical Formula 363]
[2021]
[2022] [Chemical Formula 364]
[2023]
[2024] (compound represented by general formula (4))
[2025] The compound represented by general formula (4) will be described.
[2026] [Chemical Formula 365]
[2027]
[2028] (in the above formula (4),
[2029] each Z is independently CRaor a nitrogen atom,
[2030] each of A1ring and A2ring is independently
[2031] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or
[2032] a substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms,
[2033] in the case where a plurality of Raare present, one or more groups consisting of 2 or more adjacent ones among the plurality of Ra
[2034] are bonded to each other to form a substituted or unsubstituted monocyclic ring,
[2035] are bonded to each other to form a substituted or unsubstituted fused ring, or
[2036] are not bonded to each other,
[2037] each of n21and n22is independently 0, 1, 2, 3, or 4,
[2038] in the case where a plurality of Rbare present, one or more groups consisting of 2 or more adjacent ones among the plurality of Rb
[2039] are bonded to each other to form a substituted or unsubstituted monocyclic ring,
[2040] are bonded to each other to form a substituted or unsubstituted fused ring, or
[2041] are not bonded to each other,
[2042] in the case where a plurality of Rcare present, one or more groups consisting of 2 or more adjacent ones among the plurality of Rc
[2043] are bonded to each other to form a substituted or unsubstituted monocyclic ring,
[2044] are bonded to each other to form a substituted or unsubstituted fused ring, or
[2045] are not bonded to each other,
[2046] each of Ra, Rb, and Rc, which does not form the above substituted or unsubstituted monocyclic ring and does not form the above substituted or unsubstituted fused ring, is independently
[2047] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
[2048] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
[2049] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
[2050] a substituted or unsubstituted cyclic alkenyl group having 3 to 50 ring-forming carbon atoms,
[2051] a group represented by -Si(R 901 )(R 902 )(R 903 ),
[2052] a group represented by -O-(R 904 ),
[2053] a group represented by -S-(R 905 ),
[2054] a group represented by -N(R 906 )(R 907 ),
[2055] a halogen atom,
[2056] a cyano group,
[2057] a nitro group,
[2058] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or
[2059] a substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms.
[2060] The "aromatic hydrocarbon ring" of the A1 ring and the A2 ring is the same structure as a compound obtained by introducing a hydrogen atom to the "aryl group" described above.
[2061] The "aromatic hydrocarbon ring" of the A1 ring and the A2 ring includes 2 carbon atoms on the central fused 2-ring structure of the general formula (4) as ring-forming atoms.
[2062] As a specific example of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms", a compound obtained by introducing a hydrogen atom to the "aryl group" described in the Specific Example Group G1, and the like can be given.
[2063] The "heterocyclic ring" of the A1 ring and the A2 ring is the same structure as a compound obtained by introducing a hydrogen atom to the "heterocyclic group" described above.
[2064] The "heterocyclic ring" of the A1 ring and the A2 ring includes 2 carbon atoms on the central fused 2-ring structure of the general formula (4) as ring-forming atoms.
[2065] As a specific example of the "substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms", a compound obtained by introducing a hydrogen atom to the "heterocyclic group" described in the Specific Example Group G2, and the like can be given.
[2066] Rb is bound to any one of the carbon atoms forming the aromatic hydrocarbon ring as the A1 ring, or to any one of the atoms forming the heterocyclic ring as the A1 ring.
[2067] Rc is bound to any one of the carbon atoms forming the aromatic hydrocarbon ring as the A2 ring, or to any one of the atoms forming the heterocyclic ring as the A2 ring.
[2068] Of Ra, Rb, and Rc, preferably at least one is a group represented by the following general formula (4a), and more preferably at least two are groups represented by the following general formula (4a).
[2069]
Chemical Formula 366
[2070] *-L 401 -Ar 401 (4a)
[2071] (in the above general formula (4a),
[2072] L 401 is
[2073] a single bond,
[2074] a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or
[2075] a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms,
[2076] Ar 401 is
[2077] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms,
[2078] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, or
[2079] a group represented by the following general formula (4b).
[2080]
Chemical Formula 367
[2081]
[2082] (in the above general formula (4b),
[2083] L 402 and L 403 each independently is
[2084] a single bond,
[2085] a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or
[2086] a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms,
[2087] Ar 402 and Ar 403 consisting of 2 or more adjacent groups selected from the group consisting of
[2088] are bonded to each other to form a substituted or unsubstituted monocyclic ring,
[2089] are bonded to each other to form a substituted or unsubstituted fused ring, or
[2090] are not bonded to each other,
[2091] Ar which does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted fused ring 402 and Ar 403 each independently is
[2092] a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms, or
[2093] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
[2094] In one embodiment, the compound represented by the above general formula (4) is represented by the following general formula (42).
[2095]
Chemical Formula 368
[2096]
[2097] (in the above general formula (42),
[2098] one or more groups selected from the group consisting of 2 or more adjacent groups selected from the group consisting of 401 411
[2099] are bonded to each other to form a substituted or unsubstituted monocyclic ring,
[2100] are bonded to each other to form a substituted or unsubstituted fused ring, or
[2101] are not bonded to each other,
[2102] R which does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted fused ring 401 411 each independently is
[2103] a hydrogen atom,
[2104] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
[2105] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
[2106] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
[2107] a substituted or unsubstituted alicyclic hydrocarbon group having 3 to 50 ring-forming carbon atoms,
[2108] a group represented by -Si(R 901 )(R 902 )(R 903 ),
[2109] a group represented by -O-(R 904 ),
[2110] a group represented by -S-(R 905 ),
[2111] a group represented by -N(R 906 )(R 907 ),
[2112] a halogen atom,
[2113] a cyano group,
[2114] a nitro group,
[2115] a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring-forming carbon atoms, or
[2116] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
[2117] R 401 to R 411 , at least one of which is a group represented by the above general formula (4a), and more preferably at least two of which are groups represented by the above general formula (4a).
[2118] R 404 and R 411 are groups represented by the above general formula (4a).
[2119] In one embodiment, the compound represented by the above general formula (4) is a compound in which a structure represented by the following general formula (4-1) or general formula (4-2) is bonded to the A1ring.
[2120] In addition, in one embodiment, the compound represented by the above general formula (42) is a compound in which a structure represented by the following general formula (4-1) or general formula (4-2) is bonded to the ring to which R 404 to R 407 are bonded.
[2121]
Chemical Formula 369
[2122]
[2123] (in the above general formula (4-1), the two *'s each independently bond to a ring-forming carbon atom of an aromatic hydrocarbon ring or a ring-forming atom of a heterocyclic ring that is the A1ring of the above general formula (4), or to R404 any one of the above R 407 is bonded to,
[2124] each of the three * of the above general formula (4-2) is independently bonded to a ring-forming carbon atom of an aromatic hydrocarbon ring or a ring-forming atom of a hetero ring as A1ring of the above general formula (4), or to R 404 any one of the above R 407 is bonded to,
[2125] one or more groups consisting of 2 or more adjacent ones of the above R 421 any one of the above R 427 is bonded to,
[2126] are bonded to each other to form a substituted or unsubstituted monocyclic ring,
[2127] are bonded to each other to form a substituted or unsubstituted fused ring, or
[2128] are not bonded to each other,
[2129] one or more groups consisting of 2 or more adjacent ones of the above R 431 any one of the above R 438 is bonded to,
[2130] are bonded to each other to form a substituted or unsubstituted monocyclic ring,
[2131] are bonded to each other to form a substituted or unsubstituted fused ring, or
[2132] are not bonded to each other,
[2133] R 421 any one of the above R 427 is not bonded to form the above substituted or unsubstituted monocyclic ring and is not bonded to form the above substituted or unsubstituted fused ring, 431 any one of the above R 438 is each independently
[2134] a hydrogen atom,
[2135] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[2136] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[2137] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,
[2138] a substituted or unsubstituted ring alkyl group having a ring-forming carbon number of 3 to 50,
[2139] a group represented by -Si(R 901 )(R 902 )(R 903 ),
[2140] -O-(R904 a group represented by the formula:
[2141] -S-(R 905 a group represented by the formula:
[2142] -N(R 906 )(R 907 a group represented by the formula:
[2143] a halogen atom,
[2144] a cyano group,
[2145] a nitro group,
[2146] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or
[2147] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
[2148] In one embodiment, the compound represented by the above formula (4) is a compound represented by the following formula (41-3), formula (41-4) or formula (41-5).
[2149] [Chemical Formula 370]
[2150]
[2151] [Chemical Formula 371]
[2152]
[2153] [Chemical Formula 372]
[2154]
[2155] (In the above formula (41-3), formula (41-4) and formula (41-5),
[2156] A1ring has the same meaning as in the above formula (4),
[2157] R 421 to R 427 each independently have the same meaning as R 421 to R 427 in the above formula (4-1),
[2158] R 440 to R 448 each independently have the same meaning as R 401 to R 411 in the above formula (42).
[2159] In one embodiment, the substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 ring-forming carbons as the A1ring of General Formula (41-5) above is
[2160] a substituted or unsubstituted naphthalene ring, or
[2161] a substituted or unsubstituted fluorene ring.
[2162] In one embodiment, the substituted or unsubstituted heterocyclic ring of 5 to 50 ring-forming atoms as the A1ring of General Formula (41-5) above is
[2163] a substituted or unsubstituted dibenzofuran ring,
[2164] a substituted or unsubstituted carbazole ring, or
[2165] a substituted or unsubstituted dibenzothiophene ring.
[2166] In one embodiment, the compound represented by General Formula (4) above or General Formula (42) above is selected from the group consisting of compounds represented by General Formulae (461) to (467) below.
[2167] [Chemical Formula 373]
[2168]
[2169] [Chemical Formula 374]
[2170]
[2171] [Chemical Formula 375]
[2172]
[2173] [Chemical Formula 376]
[2174]
[2175] [Chemical Formula 377]
[2176]
[2177] (In General Formulae (461), (462), (463), (464), (465), (466), and (467) above,
[2178] R 421 ~R 427 each independently has the same meaning as R 421 ~R 427 above in General Formula (4-1),
[2179] R 431 ~R438 each independently R in the above general formula (4-2) 431 ~R 438 have the same meanings,
[2180] R 440 ~R 448 and R 451 ~R 454 each independently R in the above general formula (42) 401 ~R 411 have the same meanings,
[2181] X4is an oxygen atom, NR 801 , or C(R 802 )(R 803 ),
[2182] R 801 , R 802 and R 803 each independently are
[2183] a hydrogen atom,
[2184] substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[2185] substituted or unsubstituted cycloalkyl group having a ring-constituting carbon number of 3 to 50,
[2186] substituted or unsubstituted aryl group having a ring-constituting carbon number of 6 to 50, or
[2187] substituted or unsubstituted heterocyclic group having a ring-constituting atom number of 5 to 50,
[2188] substituted or unsubstituted alkyl group having a carbon number of 1 to 50, or
[2189] substituted or unsubstituted aryl group having a ring-constituting carbon number of 6 to 50,
[2190] in case where a plurality of R 801 exist, the plurality of R 801 are the same or different from each other,
[2191] in case where a plurality of R 802 exist, the plurality of R 802 are the same or different from each other,
[2192] in case where a plurality of R 803 exist, the plurality of R 803 are the same or different from each other.
[2193] In one embodiment, in the compound represented by the above general formula (42), R 401 ~R 411one or more groups selected from the group consisting of 2 or more adjacent groups in the above-described group, are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring. For this embodiment, the compounds represented by the following General Formula (45) are specifically described.
[2194] (Compounds represented by General Formula (45))
[2195] The compounds represented by General Formula (45) are described.
[2196]
Chemical Formula 378
[2197]
[2198] (in the above General Formula (45),
[2199] from the group consisting of R 461 and R 462 from the group consisting of R 462 and R 463 from the group consisting of R 464 and R 465 from the group consisting of R 465 and R 466 from the group consisting of R 466 and R 467 from the group consisting of R 468 and R 469 from the group consisting of R 469 and R 470 from the group consisting of R 470 and R 471 from the group consisting of 2 or more groups selected from the group consisting of one or more groups selected from the group consisting of R
[2200] wherein,
[2201] from the group consisting of R 461 and R 462 from the group consisting of R 462 and R 463 ;
[2202] from the group consisting of R 464 and R 465 from the group consisting of R 465 and R 466 ;
[2203] from the group consisting of R 465 and R 466 from the group consisting of R 466 and R 467 ;
[2204] from the group consisting of R 468 and R469 The group composed of R 469 With R 470 The group formed; and
[2205] By R 469 With R 470 The group composed of R 470 With R 471 The groups do not simultaneously form a ring.
[2206] R 461 ~R 471 Two or more rings are formed that are identical or different from each other.
[2207] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 461 ~R 471 Each independently
[2208] hydrogen atom,
[2209] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2210] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2211] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2212] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2213] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2214] -O-(R 904 The groups shown in the figure,
[2215] -S-(R 905 ), -N(R 906 (R) 907 The groups shown in the figure,
[2216] Halogen atoms,
[2217] cyano,
[2218] Nitro,
[2219] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2220] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2221] In the above general formula (45), R n With R n+1(n represents an integer selected from 461, 462, 464 to 466, and 468 to 470) are bonded to each other to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring n and R n+1 The 2 ring-forming carbon atoms to which R n and R n+1 are bonded form, together, a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring. The ring is preferably composed of atoms selected from carbon atoms, oxygen atoms, sulfur atoms, and nitrogen atoms, and the number of atoms of the ring is preferably 3 to 7, more preferably 5 or 6.
[2222] The number of the above-described ring structures in the compound represented by the above-described General Formula (45) is, for example, 2, 3, or 4. Two or more of the ring structures can each exist on the same benzene ring on the parent skeleton of the above-described General Formula (45), or can exist on different benzene rings. For example, in the case of having 3 ring structures, 1 ring structure can exist on each of the 3 benzene rings of the above-described General Formula (45).
[2223] As the above-described ring structure in the compound represented by the above-described General Formula (45), for example, the structures represented by the following General Formulas (451) to (460) and the like can be given.
[2224]
Chemical Formula 379
[2225]
[2226] (In the above-described General Formulas (451) to (457),
[2227] *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14 each represent R n and R n+1 The above-described 2 ring-forming carbon atoms to which R n are bonded,
[2228] R 45 The ring-forming carbon atom to which R 4512 is bonded can be any one of the 2 ring-forming carbon atoms represented by *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14,
[2229] X 4513 is a carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom,
[2230] 1 group or more selected from a group of 2 or more adjacent ones among R 4514 to R 4501 and R 4506 to R 4512 4513
[2231] are bonded to each other to form a substituted or unsubstituted monocyclic ring,
[2232] are bonded to each other to form a substituted or unsubstituted fused ring, or
[2233] are not bonded to each other,
[2234] R 4501 ~R 4514 each independently R 461 ~R 471 have the same meaning.
[2235]
Chemical Formula 380
[2236]
[2237] (in General Formulae (458) to (460) above,
[2238] *1 and *2 and *3 and *4 respectively represent R n and R n+1 bonded to the above 2 ring-forming carbon atoms,
[2239] R n bonded to the ring-forming carbon atom can be either of the 2 ring-forming carbon atoms represented by *1 and *2 or *3 and *4,
[2240] X 45 is C(R 4512 )(R 4513 ), NR 4514 , an oxygen atom, or a sulfur atom,
[2241] one or more groups selected from the group consisting of 2 or more adjacent ones of R 4512 ~R 4513 and R 4515 ~R4 525
[2242] are bonded to each other to form a substituted or unsubstituted monocyclic ring,
[2243] are bonded to each other to form a substituted or unsubstituted fused ring, or
[2244] are not bonded to each other,
[2245] R 4512 ~R 4513 , R 4515 ~R 4521 and R 4522 ~R 4525 , and R 4514 each independently R 461 ~R471 have the same meaning.
[2246] In General Formula (45) above, at least one of R 462 , R 464 , R 465 , R 470 and R 471 (preferably at least one of R 462 , R 465 and R 470 , further preferably R 462 ) is a group not forming a ring structure.
[2247] (i) a substituent when the ring structure formed by R n and R n+1 in General Formula (45) above has a substituent,
[2248] (ii) R 461 to R 471 in General Formula (45) above which do not form a ring structure, and
[2249] (iii) R 4501 to R 4514 , R 4515 to R 4525 in Formulae (451) to (460) above, are each independently preferably any one selected from the group consisting of
[2250] a hydrogen atom,
[2251] a substituted or unsubstituted alkyl group with a carbon number of 1 to 50,
[2252] a substituted or unsubstituted alkenyl group with a carbon number of 2 to 50,
[2253] a substituted or unsubstituted alkynyl group with a carbon number of 2 to 50,
[2254] a substituted or unsubstituted cyclic alkyl group with a ring-forming carbon number of 3 to 50,
[2255] a group represented by -N(R 906 )(R 907 ),
[2256] a substituted or unsubstituted aryl group with a ring-forming carbon number of 6 to 50,
[2257] a substituted or unsubstituted heterocyclic group with a ring-forming atom number of 5 to 50, or
[2258] a group represented by General Formula (461) to General Formula (464) below.
[2259]
Chemical Formula 381
[2260]
[2261] (in the above general formulae (461) to (464),
[2262] R d each independently is
[2263] a hydrogen atom,
[2264] a substituted or unsubstituted alkyl group with a carbon atom number of 1 to 50,
[2265] a substituted or unsubstituted alkenyl group with a carbon atom number of 2 to 50,
[2266] a substituted or unsubstituted alkynyl group with a carbon atom number of 2 to 50,
[2267] a substituted or unsubstituted cyclic alkyl group with a ring-constituting carbon atom number of 3 to 50,
[2268] a group represented by -Si(R 901 )(R 902 )(R 903 ),
[2269] a group represented by -O-(R 904 ),
[2270] a group represented by -S-(R 905 ),
[2271] a group represented by -N(R 906 )(R 907 ),
[2272] a halogen atom,
[2273] a cyano group,
[2274] a nitro group,
[2275] a substituted or unsubstituted aryl group with a ring-constituting carbon atom number of 6 to 50, or
[2276] a substituted or unsubstituted heterocyclic group with a ring-constituting atom number of 5 to 50,
[2277] X 46 is C(R 801 )(R 802 ), NR 803 , an oxygen atom or a sulfur atom,
[2278] R 801 , R 802 and R 803 each independently are
[2279] a hydrogen atom,
[2280] a substituted or unsubstituted alkyl group with a carbon atom number of 1 to 50,
[2281] substituted or unsubstituted cycloalkyl having 3 to 50 ring-forming carbons,
[2282] substituted or unsubstituted aryl having 6 to 50 ring-forming carbons, or
[2283] substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,
[2284] substituted or unsubstituted alkyl having 1 to 50 carbons, or
[2285] substituted or unsubstituted aryl having 6 to 50 ring-forming carbons,
[2286] in R 801 in the case where a plurality of R 801 are the same as or different from each other,
[2287] in R 802 in the case where a plurality of R 802 are the same as or different from each other,
[2288] in R 803 in the case where a plurality of R 803 are the same as or different from each other,
[2289] p1 is 5,
[2290] p2 is 4,
[2291] p3 is 3,
[2292] p4 is 7,
[2293] each of * in the above general formulae (461) to (464) independently represents a bonding position to a ring structure.
[2294] in the third compound and the fourth compound, R 901 to R 907 are the same as or different from each other.
[2295] In one embodiment, the compound represented by the above general formula (45) is represented by any one of the following general formulae (45-1) to (45-6).
[2296] [Chemical Formula 382]
[2297]
[2298] [Chemical Formula 383]
[2299]
[2300] (in the above general formulae (45-1) to (45-6),
[2301] Each of rings d to i is independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring,
[2302] R 461 ~R 471 Each of R1to R4in the above general formula (45) is independently 461 ~R 471 identical to the meaning.
[2303] In one embodiment, the compound represented by the above general formula (45) is represented by any one of the following general formulae (45-7) to (45-12).
[2304] [Chemical Formula 384]
[2305]
[2306] [Chemical Formula 385]
[2307]
[2308] (in the above general formulae (45-7) to (45-12),
[2309] Each of rings d to f, k, j is independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring,
[2310] R 461 ~R 471 Each of R1to R4in the above general formula (45) is independently 461 ~R 471 identical to the meaning.
[2311] In one embodiment, the compound represented by the above general formula (45) is represented by any one of the following general formulae (45-13) to (45-21).
[2312] [Chemical Formula 386]
[2313]
[2314] [Chemical Formula 387]
[2315]
[2316] [Chemical Formula 388]
[2317]
[2318] (in the above general formulae (45-13) to (45-21),
[2319] Each of rings d to k is independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring,
[2320] R461 ~R 471 each independently R 461 ~R 471 have the same meanings.
[2321] As the substituent further having a substituent on the above-described ring g or the above-described ring h, for example, a
[2322] substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[2323] substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50,
[2324] a group represented by the above-described general formula (461),
[2325] a group represented by the above-described general formula (463), or
[2326] a group represented by the above-described general formula (464).
[2327] In one embodiment, the compound represented by the above-described general formula (45) is represented by any one of the following general formulae (45-22) to (45-25).
[2328]
Chemical Formula 389
[2329]
[2330] (in the above-described general formulae (45-22) to (45-25),
[2331] X 46 and X 47 each independently C(R 801 )(R 802 ), NR 803 , an oxygen atom, or a sulfur atom,
[2332] R 461 ~R 471 and R 481 ~R 488 each independently R 461 ~R 471 have the same meanings.
[2333] R 801 , R 802 , and R 803 each independently are
[2334] a hydrogen atom,
[2335] substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[2336] substituted or unsubstituted cycloalkyl group having a ring-forming carbon number of 3 to 50,
[2337] substituted or unsubstituted aryl group having a ring-constituting carbon number of 6 to 50, or
[2338] substituted or unsubstituted heterocyclic group having a ring-constituting atom number of 5 to 50,
[2339] substituted or unsubstituted alkyl group having a carbon number of 1 to 50, or
[2340] substituted or unsubstituted aryl group having a ring-constituting carbon number of 6 to 50,
[2341] R 801 in the case where a plurality of R 801 are present, the plurality of R 802 are the same or different from each other,
[2342] R 802 in the case where a plurality of R 803 are present, the plurality of R 803 are the same or different from each other.
[2343] R 46 in the case where a plurality of R 801 are present, the plurality of R 802 are the same or different from each other.
[2344] In one embodiment, the compound represented by General Formula (45) described above is represented by General Formula (45-26).
[2345]
Chemical Formula 390
[2346]
[2347] (in General Formula (45-26) described above,
[2348] X 803 is C(R 463 )(R 464 ), NR 467 , an oxygen atom, or a sulfur atom,
[2349] R 468 , R 471 , R 481 , R 492 , R 461 , and R 471 each independently have the same meaning as R
[2350] R 801 , R 802 , and R 803 each independently are
[2351] a hydrogen atom,
[2352] substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[2353] substituted or unsubstituted cycloalkyl group having a ring-forming carbon number of 3 to 50,
[2354] substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50, or
[2355] substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50,
[2356] substituted or unsubstituted alkyl group having a carbon number of 1 to 50, or
[2357] substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50,
[2358] in R 801 in the case where a plurality of R 801 are present, the plurality of R
[2359] in R 802 in the case where a plurality of R 802 are present, the plurality of R
[2360] in R 803 in the case where a plurality of R 803 are present, the plurality of R
[2361] As the compound represented by the above general formula (4), for example, the following compounds represented by the following general formulae can be mentioned as specific examples. In the following specific examples, Ph represents a phenyl group, and D represents a deuterium atom.
[2362] [Chemical Formula 391]
[2363]
[2364] [Chemical Formula 392]
[2365]
[2366] [Chemical Formula 393]
[2367]
[2368] [Chemical Formula 394]
[2369]
[2370] [Chemical Formula 395]
[2371]
[2372] [Chemical Formula 396]
[2373]
[2374] [Chemical Formula 397]
[2375]
[2376] [Chemical Formula 398]
[2377]
[2378] [Chemical Formula 399]
[2379]
[2380] [Chemical Formula 400]
[2381]
[2382] (compound represented by General Formula (5))
[2383] A compound represented by General Formula (5) will be described. The compound represented by General Formula (5) is a compound corresponding to the compound represented by General Formula (41-3) described above.
[2384] [Chemical Formula 401]
[2385]
[2386] (in General Formula (5) described above,
[2387] one or more groups selected from the group consisting of R 501 ~R 507 and R 511 ~R 517 one or more groups selected from the group consisting of 2 or more adjacent groups among R
[2388] are bonded to each other to form a substituted or unsubstituted monocyclic ring,
[2389] are bonded to each other to form a substituted or unsubstituted fused ring, or
[2390] are not bonded to each other,
[2391] R is not formed into the above-described substituted or unsubstituted monocyclic ring and is not formed into the above-described substituted or unsubstituted fused ring 501 ~R 507 and R 511 ~R 517 each independently is
[2392] a hydrogen atom,
[2393] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[2394] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[2395] substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[2396] substituted or unsubstituted cycloalkyl group having a ring-constituting carbon number of 3 to 50,
[2397] a group represented by -Si(R 901 )(R 902 )(R 903 ),
[2398] a group represented by -O-(R 904 ),
[2399] a group represented by -S-(R 905 ),
[2400] a group represented by -N(R 906 )(R 907 ),
[2401] a halogen atom,
[2402] a cyano group,
[2403] a nitro group,
[2404] substituted or unsubstituted aryl group having a ring-constituting carbon number of 6 to 50, or
[2405] substituted or unsubstituted heterocyclic group having a ring-constituting atom number of 5 to 50.
[2406] R 521 and R 522 are each independently
[2407] a hydrogen atom,
[2408] substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[2409] substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[2410] substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,
[2411] substituted or unsubstituted cycloalkyl group having a ring-constituting carbon number of 3 to 50,
[2412] a group represented by -Si(R 901 )(R 902 )(R 903 ),
[2413] a group represented by -O-(R 904 ),
[2414] a group represented by -S-(R 905 ),
[2415] a group represented by -N(R 906) a group represented by -N(R 907 ),
[2416] a halogen atom,
[2417] a cyano group,
[2418] a nitro group,
[2419] a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms, or
[2420] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
[2421] "one group selected from the group consisting of two or more adjacent groups selected from the group consisting of R 501 to R 507 and R 511 to R 517 is, for example, a group consisting of R 501 and R 502 , a group consisting of R 502 and R 503 , a group consisting of R 503 and R 504 , a group consisting of R 505 and R 506 , a group consisting of R 506 and R 507 , a group consisting of R 501 and R 502 , and a group consisting of R 503 and R 501 .
[2422] In one embodiment, at least one of R 507 to R 511 and R 517 to R 906 is a group represented by -N(R 907 )(R 501 ).
[2423] In one embodiment, each of R 507 to R 511 and R 517 is independently
[2424] a hydrogen atom,
[2425] a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms, or
[2426] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
[2427] In one embodiment, the compound represented by the above general formula (5) is a compound represented by the following general formula (52).
[2428] [Chemical Formula 402]
[2429]
[2430] (in the above general formula (52), R
[2431] R 531 ~R 534 , and R 541 ~R 544 one or more groups selected from the group consisting of 2 or more adjacent groups among R
[2432] are bonded to each other to form a substituted or unsubstituted monocyclic ring,
[2433] are bonded to each other to form a substituted or unsubstituted fused ring, or
[2434] are not bonded to each other,
[2435] R 531 ~R 534 , R 541 ~R 544 , and R 551 and R 552 are each independently
[2436] a hydrogen atom,
[2437] a substituted or unsubstituted aromatic group having a ring-constituting carbon number of 6 to 50, or
[2438] a substituted or unsubstituted heterocyclic group having a ring-constituting atom number of 5 to 50,
[2439] R 561 ~R 564 are each independently
[2440] a substituted or unsubstituted aromatic group having a ring-constituting carbon number of 6 to 50, or
[2441] a substituted or unsubstituted heterocyclic group having a ring-constituting atom number of 5 to 50.
[2442] In one embodiment, the compound represented by the above general formula (5) is a compound represented by the following general formula (53).
[2443] [Chemical Formula 403]
[2444]
[2445] (in the above general formula (53), R 551 , R 552 , and R 561 ~R 564 are each independentlyEach independently relates to R in the above general formula (52) 551 R 552 and R 561 ~R 564 The meaning is the same.
[2446] 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.
[2447] 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.
[2448] In one embodiment, the substituents expressed as "substituted or unsubstituted" in the above general formulas (5), (52), and (53) are...
[2449] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2450] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2451] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2452] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2453] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2454] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[2455] As a compound represented by the above general formula (5), the following compounds can be cited as specific examples.
[2456] Chemical formula 404
[2457]
[2458]
Chemical Formula 405
[2459]
[2460] Chemical formula 406
[2461]
[2462] [Chemical Formula 407]
[2463]
[2464] [Chem. 408]
[2465]
[2466] [Chem. 409]
[2467]
[2468] [Chem. 410]
[2469]
[2470] [Chem. 411]
[2471]
[2472] [Chem. 412]
[2473]
[2474] [Chem. 413]
[2475]
[2476] [Chem. 414]
[2477]
[2478] [Chem. 415]
[2479]
[2480] [Chem. 416]
[2481]
[2482] [Chem. 417]
[2483]
[2484] [Chem. 418]
[2485]
[2486] [Chem. 419]
[2487]
[2488] [Chem. 420]
[2489]
[2490] (a compound represented by General Formula (6))
[2491] A compound represented by General Formula (6) is described.
[2492]
Chemical Formula 421
[2493]
[2494] (in General Formula (6) above,
[2495] a ring, a b ring, and a c ring are each independently
[2496] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbons, or
[2497] a substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms,
[2498] R 601 and R 602 each independently form a substituted or unsubstituted heterocyclic ring by binding to the above-described a ring, b ring, or c ring, or do not form a substituted or unsubstituted heterocyclic ring,
[2499] R 601 and R 602 each independently are
[2500] a substituted or unsubstituted alkyl group having 1 to 50 carbons,
[2501] a substituted or unsubstituted alkenyl group having 2 to 50 carbons,
[2502] a substituted or unsubstituted alkynyl group having 2 to 50 carbons,
[2503] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbons,
[2504] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbons, or
[2505] a substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms.
[2506] a ring, a b ring, and a c ring are rings (a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbons, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms) fused to the central fused 2-ring structure of General Formula (6) described above composed of a boron atom and 2 nitrogen atoms.
[2507] The "aromatic hydrocarbon ring" of a ring, a b ring, and a c ring is the same structure as a compound in which a hydrogen atom is introduced to the above-described "aryl group".
[2508] The "aromatic hydrocarbon ring" of a ring includes 3 carbon atoms on the central fused 2-ring structure of General Formula (6) as ring-forming atoms.
[2509] The "aromatic hydrocarbon ring" of the b ring and the c ring includes 2 carbon atoms on the central fused 2-ring structure of the above general formula (6) as ring-forming atoms.
[2510] As specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms", compounds obtained by introducing hydrogen atoms to the "aryl group" described in the specific example group G1, and the like can be given.
[2511] The "hetero ring" of the a ring, the b ring, and the c ring is the same structure as a compound obtained by introducing hydrogen atoms to the above "hetero ring group".
[2512] The "hetero ring" of the a ring includes 3 carbon atoms on the central fused 2-ring structure of the above general formula (6) as ring-forming atoms. The "hetero ring" of the b ring and the c ring includes 2 carbon atoms on the central fused 2-ring structure of the above general formula (6) as ring-forming atoms. As specific examples of the "substituted or unsubstituted hetero ring having 5 to 50 ring-forming atoms", compounds obtained by introducing hydrogen atoms to the "hetero ring group" described in the specific example group G2, and the like can be given.
[2513] R 601 and R 602 Each independently can be bonded to the a ring, the b ring, or the c ring to form a substituted or unsubstituted hetero ring. The hetero ring at this time includes a nitrogen atom on the central fused 2-ring structure of the above general formula (6). The hetero ring at this time can also include a hetero atom other than the nitrogen atom. R 601 and R 602 Bonding to the a ring, the b ring, or the c ring specifically means that the atoms constituting the a ring, the b ring, or the c ring are bonded to the atoms constituting R 601 and R 602 . For example, it can also be that R 601 is bonded to the a ring to form a nitrogen-containing hetero ring in which a ring including R 601 is fused to the a ring in 2-ring (or 3-ring or more) fusion. As specific examples of this nitrogen-containing hetero ring, compounds corresponding to the 2-ring or more fused hetero ring groups including nitrogen in the specific example group G2, and the like can be given.
[2514] R 601 is bonded to the b ring, R 602 is bonded to the a ring, and R 602 is bonded to the c ring are the same as above.
[2515] In one embodiment, the a ring, the b ring, and the c ring in the above general formula (6) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms.
[2516] In one embodiment, each of the rings a, b, and c in the above general formula (6) is independently a substituted or unsubstituted benzene ring or naphthalene ring.
[2517] In one embodiment, R 601 and R 602 are each independently
[2518] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbons, or
[2519] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,
[2520] and preferably a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbons.
[2521] In one embodiment, the compound represented by the above general formula (6) is a compound represented by the following general formula (62).
[2522]
Chemical Formula 422
[2523]
[2524] (In the above general formula (62),
[2525] R 601A and R 611 are each independently 621 form a substituted or unsubstituted heterocyclic ring, or do not form a substituted or unsubstituted heterocyclic ring,
[2526] R 602A and R 613 are each independently 614 form a substituted or unsubstituted heterocyclic ring, or do not form a substituted or unsubstituted heterocyclic ring,
[2527] R 601A and R 602A are each independently
[2528] a substituted or unsubstituted alkyl group having 1 to 50 carbons,
[2529] a substituted or unsubstituted alkenyl group having 2 to 50 carbons,
[2530] a substituted or unsubstituted alkynyl group having 2 to 50 carbons,
[2531] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbons,
[2532] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbons, or
[2533] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,
[2534] R 611 R 621 1 or more groups selected from the group consisting of 2 or more adjacent groups among R
[2535] bonded to each other to form a substituted or unsubstituted monocyclic,
[2536] bonded to each other to form a substituted or unsubstituted fused ring, or
[2537] not bonded to each other,
[2538] R which does not form the above-mentioned substituted or unsubstituted heterocyclic ring, does not form the above-mentioned substituted or unsubstituted monocyclic ring, and does not form the above-mentioned substituted or unsubstituted fused ring 611 R 621 each independently is
[2539] a hydrogen atom,
[2540] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[2541] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[2542] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,
[2543] a substituted or unsubstituted cyclic alkyl group having a ring-forming carbon number of 3 to 50,
[2544] -Si(R 901 )(R 902 )(R 903 ),
[2545] -O-(R 904 ),
[2546] -S-(R 905 ),
[2547] -N(R 906 )(R 907 ),
[2548] a halogen atom,
[2549] a cyano group,
[2550] a nitro group,
[2551] a substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50, or
[2552] a substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50.
[2553] R 601A and R602A R 601 and R 602 corresponding groups.
[2554] For example, R 601A and R 611 may be bonded to form a 2-ring fused (or 3 or more rings fused) nitrogen-containing heterocycle having a ring including them and a benzene ring corresponding to the a ring. As specific examples of the nitrogen-containing heterocycle, compounds corresponding to the 2 or more rings fused heterocyclic groups containing nitrogen in the specific example group G2, and the like can be given. R 601A and R 621 may be bonded, R 602A and R 613 may be bonded, and R 602A and R 614 may be bonded are the same as above.
[2555] One or more groups in a group consisting of two or more adjacent groups among R 611 to R 621 may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or
[2556] a substituted or unsubstituted fused ring.
[2557] a substituted or unsubstituted fused ring.
[2558] For example, R 611 and R 612 may be bonded to form a structure in which a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring, or the like is fused to a six-membered ring to which they are bonded, and the formed fused ring becomes a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring.
[2559] In one embodiment, R 611 to R 621 each independently are
[2560] a hydrogen atom,
[2561] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[2562] a substituted or unsubstituted aromatic group having a ring-forming carbon number of 6 to 50, or
[2563] a substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50.
[2564] In one embodiment, R 611 to R 621 each independently are
[2565] a hydrogen atom,
[2566] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or
[2567] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
[2568] In one embodiment, R 611 to R 621 are each independently
[2569] a hydrogen atom, or
[2570] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[2571] In one embodiment, R 611 to R 621 are each independently
[2572] a hydrogen atom, or
[2573] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
[2574] R 611 to R 621 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[2575] In one embodiment, the compound represented by General Formula (62) described above is a compound represented by General Formula (63) described below.
[2576]
Chemical Formula 423
[2577]
[2578] (In General Formula (63) described above,
[2579] R 631 and R 646 are bonded to form a substituted or unsubstituted heterocyclic ring, or do not form a substituted or unsubstituted heterocyclic ring,
[2580] R 633 and R 647 are bonded to form a substituted or unsubstituted heterocyclic ring, or do not form a substituted or unsubstituted heterocyclic ring,
[2581] R 634 and R 651 are bonded to form a substituted or unsubstituted heterocyclic ring, or do not form a substituted or unsubstituted heterocyclic ring,
[2582] R 641 and R 642 are bonded to form a substituted or unsubstituted heterocyclic ring, or do not form a substituted or unsubstituted heterocyclic ring,
[2583] R631 ~R 651 1 group or more selected from the group consisting of 2 or more adjacent groups among R
[2584] are linked to each other to form a substituted or unsubstituted monocyclic ring,
[2585] are linked to each other to form a substituted or unsubstituted fused ring, or
[2586] are not linked to each other,
[2587] R which does not form the above-mentioned substituted or unsubstituted heterocyclic ring, does not form the above-mentioned substituted or unsubstituted monocyclic ring, and does not form the above-mentioned substituted or unsubstituted fused ring 631 ~R 651 each independently is
[2588] a hydrogen atom,
[2589] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[2590] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[2591] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,
[2592] a substituted or unsubstituted cyclic alkyl group having a ring-forming carbon number of 3 to 50,
[2593] -Si(R 901 )(R 902 )(R 903 ) group,
[2594] an -O-(R 904 ) group,
[2595] an -S-(R 905 ) group,
[2596] an -N(R 906 )(R 907 ) group,
[2597] a halogen atom,
[2598] a cyano group,
[2599] a nitro group,
[2600] a substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50, or
[2601] a substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50.
[2602] R 631 may be linked to R 646 to form a substituted or unsubstituted heterocyclic ring. For example, R 631bonded to form a fused ring with R 646 bonded to form a fused ring with R 646 a nitrogen-containing heterocyclic ring fused to the benzene ring bonded, the ring containing N, and the benzene ring corresponding to the ring a. As specific examples of the nitrogen-containing heterocyclic ring, compounds corresponding to the heterocyclic group in which a nitrogen-containing 3 or more rings are fused in Group G2, and the like can be given. R 633 bonded to form a fused ring with R 647 bonded to form a fused ring with R 634 bonded to form a fused ring with R 651 bonded to form a fused ring with R 641 bonded to form a fused ring with R 642 bonded to form a fused ring with R
[2603] In one embodiment, R 631 ~R 651 each independently is
[2604] a hydrogen atom,
[2605] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[2606] a substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50, or
[2607] a substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50.
[2608] In one embodiment, R 631 ~R 651 each independently is
[2609] a hydrogen atom,
[2610] a substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50, or
[2611] a substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50.
[2612] In one embodiment, R 631 ~R 651 each independently is
[2613] a hydrogen atom, or
[2614] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50.
[2615] In one embodiment, R 631 ~R 651 each independently is
[2616] a hydrogen atom, or
[2617] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[2618] R 631 ~R 651 at least one of R
[2619] In one embodiment, the compound represented by General Formula (63) described above is a compound represented by General Formula (63A) described below.
[2620]
Chemical Formula 424
[2621]
[2622] (in General Formula (63A) described above,
[2623] R 661 is
[2624] a hydrogen atom,
[2625] a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 50,
[2626] a substituted or unsubstituted alkenyl group having a carbon atom number of 2 to 50,
[2627] a substituted or unsubstituted alkynyl group having a carbon atom number of 2 to 50,
[2628] a substituted or unsubstituted cyclic alkyl group having a ring-constituting carbon atom number of 3 to 50, or
[2629] a substituted or unsubstituted aryl group having a carbon atom number of 6 to 50,
[2630] R 662 ~R 665 each independently is
[2631] a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 50,
[2632] a substituted or unsubstituted alkenyl group having a carbon atom number of 2 to 50,
[2633] a substituted or unsubstituted alkynyl group having a carbon atom number of 2 to 50,
[2634] a substituted or unsubstituted cyclic alkyl group having a ring-constituting carbon atom number of 3 to 50, or
[2635] a substituted or unsubstituted aryl group having a carbon atom number of 6 to 50.
[2636] In one embodiment, R 661 ~R 665 each independently is
[2637] a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 50, or
[2638] a substituted or unsubstituted aryl group having a carbon atom number of 6 to 50.
[2639] In one embodiment, R 661 ~R 665 each independently is substituted or unsubstituted alkyl of carbon number 1 to 50.
[2640] In one embodiment, the compound represented by the above general formula (63) is a compound represented by the following general formula (63B).
[2641]
Chemical Formula 425
[2642]
[2643] (in the above general formula (63B),
[2644] R 671 and R 672 each independently is
[2645] a hydrogen atom,
[2646] substituted or unsubstituted alkyl of carbon number 1 to 50,
[2647] substituted or unsubstituted alkenyl of carbon number 2 to 50,
[2648] substituted or unsubstituted alkynyl of carbon number 2 to 50,
[2649] substituted or unsubstituted cyclic alkyl of ring-forming carbon number 3 to 50,
[2650] a group represented by -N(R 906 )(R 907 ), or
[2651] substituted or unsubstituted aryl of ring-forming carbon number 6 to 50,
[2652] R 673 ~R 675 each independently is
[2653] substituted or unsubstituted alkyl of carbon number 1 to 50,
[2654] substituted or unsubstituted alkenyl of carbon number 2 to 50,
[2655] substituted or unsubstituted alkynyl of carbon number 2 to 50,
[2656] substituted or unsubstituted cyclic alkyl of ring-forming carbon number 3 to 50,
[2657] a group represented by -N(R 906 )(R 907 ), or
[2658] substituted or unsubstituted aryl of ring-forming carbon number 6 to 50.
[2659] In one embodiment, the compound represented by General Formula (63) described above is a compound represented by General Formula (63B').
[2660]
Chemical Formula 426
[2661]
[2662] (In General Formula (63B') described above, R 672 ~R 675 each independently have the same meaning as R 672 ~R 675 in General Formula (63B) described above.
[2663] In one embodiment, at least one of R 671 ~R 675 is
[2664] substituted or unsubstituted alkyl with a carbon number of 1 to 50,
[2665] substituted or unsubstituted alkenyl with a carbon number of 2 to 50,
[2666] substituted or unsubstituted alkynyl with a carbon number of 2 to 50,
[2667] substituted or unsubstituted cycloalkyl with a ring-forming carbon number of 3 to 50,
[2668] a group represented by -N(R 906 )(R 907 ), or
[2669] substituted or unsubstituted aryl with a ring-forming carbon number of 6 to 50.
[2670] In one embodiment,
[2671] R 672 is
[2672] a hydrogen atom,
[2673] substituted or unsubstituted alkyl with a carbon number of 1 to 50,
[2674] a group represented by -N(R 906 )(R 907 ), or
[2675] substituted or unsubstituted aryl with a ring-forming carbon number of 6 to 50,
[2676] R 671 and R 673 ~R 675 each independently are
[2677] substituted or unsubstituted alkyl with a carbon number of 1 to 50,
[2678] -N(R 906 (R) 907 The group shown in the figure, or
[2679] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.
[2680] In one embodiment, the compound represented by the above general formula (63) is the compound represented by the following general formula (63C).
[2681] [Chemical Formula 427]
[2682]
[2683] (In the above general formula (63C),
[2684] R 681 and R 682 Each independently
[2685] hydrogen atom,
[2686] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2687] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2688] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2689] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or
[2690] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.
[2691] R 683 ~R 686 Each independently
[2692] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2693] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2694] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2695] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or
[2696] (Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic structure.)
[2697] In one embodiment, the compound represented by the above general formula (63) is the compound represented by the following general formula (63C').
[2698] [Chemical Formula 428]
[2699]
[2700] (in the above general formula (63C'), R 683 ~R 686 each independently R 683 ~R 686 have the same meanings as those in the above general formula (63C).
[2701] In one embodiment, R 681 ~R 686 each independently is
[2702] substituted or unsubstituted alkyl having a carbon number of 1 to 50, or
[2703] substituted or unsubstituted aryl having a ring-forming carbon number of 6 to 50.
[2704] In one embodiment, R 681 ~R 686 each independently is substituted or unsubstituted aryl having a ring-forming carbon number of 6 to 50.
[2705] For the compound represented by the above general formula (6), the a ring, the b ring, and the c ring can be first bonded using a linking group (a group containing N-R 601 and a group containing N-R 602 ) to thereby produce an intermediate (1st reaction), and the a ring, the b ring, and the c ring can be bonded using a linking group (a group containing a boron atom) to produce a final product (2nd reaction). In the 1st reaction, an amination reaction such as Buchwald-Hartwig reaction can be applied. In the 2nd reaction, a Tandem Hetero Friedel-Crafts Reaction or the like can be applied.
[2706] Although specific examples of the compound represented by the above general formula (6) are described below, these are merely examples, and the compound represented by the above general formula (6) is not limited to the specific examples described below.
[2707]
Chemical Formula 429
[2708]
[2709]
Chemical Formula 430
[2710]
[2711]
Chemical Formula 431
[2712]
[2713]
Chemical Formula 432
[2714]
[2715] [Chemical Formula 433]
[2716]
[2717] [Chemical Formula 434]
[2718]
[2719] [Chemical Formula 435]
[2720]
[2721] [Chemical Formula 436]
[2722]
[2723] [Chemical Formula 437]
[2724]
[2725] [Chemical Formula 438]
[2726]
[2727] [Chemical Formula 439]
[2728]
[2729] [Chemical Formula 440]
[2730]
[2731] (Compound represented by General Formula (7))
[2732] The compound represented by General Formula (7) is described.
[2733] [Chemical Formula 441]
[2734]
[2735] [Chemical Formula 442]
[2736]
[2737] (In General Formula (7) above,
[2738] r ring is a ring represented by General Formula (72) or General Formula (73) fused at any position of the adjacent ring,
[2739] q ring and s ring are each independently a ring represented by General Formula (74) fused at any position of the adjacent ring,
[2740] each of p ring and t ring is independently a structure represented by General Formula (75) or General Formula (76) shown below, which is fused at any position of the adjacent ring,
[2741] X7is an oxygen atom, a sulfur atom, or NR 702 .
[2742] In the case where a plurality of R 701 In the case where a plurality of R 701
[2743] are bonded to each other to form a substituted or unsubstituted monocyclic,
[2744] are bonded to each other to form a substituted or unsubstituted fused ring, or
[2745] are not bonded to each other,
[2746] R 701 and R 702 are each independently
[2747] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[2748] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[2749] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,
[2750] a substituted or unsubstituted cyclic alkyl group having a ring-forming carbon number of 3 to 50,
[2751] a group represented by -Si(R 901 )(R 902 )(R 903 ),
[2752] a group represented by -O-(R 904 ),
[2753] a group represented by -S-(R 905 ),
[2754] a group represented by -N(R 906 )(R 907 ),
[2755] a halogen atom,
[2756] a cyano group,
[2757] a nitro group,
[2758] a substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50, or
[2759] a substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50,
[2760] Ar 701 and Ar 702 each independently is
[2761] substituted or unsubstituted alkyl of carbon number 1 to 50,
[2762] substituted or unsubstituted alkenyl of carbon number 2 to 50,
[2763] substituted or unsubstituted alkynyl of carbon number 2 to 50,
[2764] substituted or unsubstituted cycloalkyl of ring-forming carbon number 3 to 50,
[2765] substituted or unsubstituted aryl of ring-forming carbon number 6 to 50, or
[2766] substituted or unsubstituted heterocyclic group of ring-forming atom number 5 to 50,
[2767] L 701 is
[2768] substituted or unsubstituted alkylene of carbon number 1 to 50,
[2769] substituted or unsubstituted alkenylene of carbon number 2 to 50,
[2770] substituted or unsubstituted alkynylene of carbon number 2 to 50,
[2771] substituted or unsubstituted cycloalkylene of ring-forming carbon number 3 to 50,
[2772] substituted or unsubstituted arylene of ring-forming carbon number 6 to 50, or
[2773] substituted or unsubstituted divalent heterocyclic group of ring-forming atom number 5 to 50,
[2774] m1 is 0, 1 or 2,
[2775] m2 is 0, 1, 2, 3 or 4,
[2776] m3 is each independently 0, 1, 2 or 3,
[2777] m4 is each independently 0, 1, 2, 3, 4 or 5,
[2778] in the case where a plurality of R 701 are present, the plurality of R 701 are the same or different from each other,
[2779] in the case where a plurality of X7 are present, the plurality of X7 are the same or different from each other,
[2780] in the case where a plurality of R 702 are present, the plurality of R 702each independently of one another,
[2781] in Ar 701 in the case where a plurality of Ar 701 each independently of one another,
[2782] in Ar 702 in the case where a plurality of Ar 702 each independently of one another,
[2783] in L 701 in the case where a plurality of L 701 each independently of one another.
[2784] In the above formula (7), each of the p ring, the q ring, the r ring, the s ring, and the t ring is condensed with the adjacent ring by 2 carbon atoms. The position and the direction of the condensation are not limited, and the condensation can be performed at any position and in any direction.
[2785] In one embodiment, in the above formula (72) or formula (73) as the r ring, m1 = 0 or m2 = 0.
[2786] In one embodiment, the compound represented by the above formula (7) is represented by any one of the following formulas (71-1) to (71-6).
[2787]
Chemical Formula 443
[2788]
[2789]
Chemical Formula 444
[2790]
[2791]
Chemical Formula 445
[2792]
[2793]
Chemical Formula 446
[2794]
[2795]
Chemical Formula 447
[2796]
[2797]
Chemical Formula 448
[2798]
[2799] (In the above formulas (71-1) to (71-6), R 701 , X7, Ar 701 , Ar702 , L 701 , m1and m3have the same meanings as R 701 , X7, Ar 701 , Ar 702 , L 701 , m1and m3have the same meanings as R
[2800] In one embodiment, the compound represented by General Formula (7) is represented by any one of General Formula (71-11) to General Formula (71-13).
[2801]
Chemical Formula 449
[2802]
[2803]
Chemical Formula 450
[2804]
[2805]
Chemical Formula 451
[2806]
[2807] (General Formula (71-11) to General Formula (71-13), R 701 , X7, Ar 701 , Ar 702 , L 701 , m1, m3, and m4have the same meanings as R 701 , X7, Ar 701 , Ar 702 , L 701 , m1, m3, and m4have the same meanings as R
[2808] In one embodiment, the compound represented by General Formula (7) is represented by any one of General Formula (71-21) to General Formula (71-25).
[2809]
Chemical Formula 452
[2810]
[2811]
Chemical Formula 453
[2812]
[2813]
Chemical Formula 454
[2814]
[2815]
Chemical Formula 455
[2816]
[2817] [Chemical Formula 456]
[2818]
[2819] (In the above General Formula (71-21) to General Formula (71-25), R 701 , X7, Ar 701 , Ar 702 , L 701 , m1, and m4 have the same meanings as R 701 , X7, Ar 701 , Ar 702 , L 701 , m1, and m4 in General Formula (7).
[2820] In one embodiment, the compound represented by General Formula (7) is represented by any one of the following General Formula (71-31) to General Formula (71-33).
[2821] [Chemical Formula 457]
[2822]
[2823] [Chemical Formula 458]
[2824]
[2825] [Chemical Formula 459]
[2826]
[2827] (In the above General Formula (71-31) to General Formula (71-33), R 701 , X7, Ar 701 , Ar 702 , L 701 , m2 to m4 have the same meanings as R 701 , X7, Ar 701 , Ar 702 , L 701 , m2 to m4 in General Formula (7).
[2828] In one embodiment, Ar 701 and Ar 702 are each independently a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbons.
[2829] In one embodiment, one of Ar 701 and Ar 702 is a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbons, and the other is hydrogen. 701 702 one of the other is a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
[2830] As the compound represented by the above general formula (7), for example, the following compounds can be mentioned as specific examples.
[2831] [Chemical Formula 460]
[2832]
[2833] [Chemical Formula 461]
[2834]
[2835] [Chemical Formula 462]
[2836]
[2837] [Chemical Formula 463]
[2838]
[2839] [Chemical Formula 464]
[2840]
[2841] [Chemical Formula 465]
[2842]
[2843] (compound represented by general formula (8))
[2844] The compound represented by general formula (8) will be described.
[2845] [Chemical Formula 466]
[2846]
[2847] (in the above general formula (8),
[2848] R 801 and R 802 , R 802 and R 803 , and R 803 and R 804 of at least one group are bonded to each other to form a bivalent group represented by the following general formula (82),
[2849] R 805 and R 806 , R 806 and R 807 , and R 807 and R 808At least one group of the radicals bonds together to form a divalent group as shown in the general formula (83).
[2850] [Chemical Formula 467]
[2851]
[2852] (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),
[2853] 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),
[2854] X8 represents an oxygen atom, a sulfur atom, or NR. 809 ,
[2855] 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
[2856] hydrogen atom,
[2857] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2858] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2859] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2860] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2861] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2862] -O-(R 904 The groups shown in the figure,
[2863] -S-(R 905a group represented by the formula:
[2864] -N(R 906 )(R 907 a group represented by the formula:
[2865] a halogen atom,
[2866] a cyano group,
[2867] a nitro group,
[2868] a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms, or
[2869] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
[2870]
Chemical Formula 468
[2871]
[2872] (in the above formula (84),
[2873] Ar 801 and Ar 802 each independently is
[2874] a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms, or
[2875] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,
[2876] L 801 ~L 803 each independently is
[2877] a single bond,
[2878] a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms,
[2879] a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms, or
[2880] a divalent linking group formed by bonding 2 to 4 groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms,
[2881] * in the above formula (84) indicates a bonding position to the ring structure represented by the above formula (8), the group represented by the formula (82), or the group represented by the formula (83).
[2882] In the above formula (8), the position at which the divalent group represented by the above formula (82) and the divalent group represented by the formula (83) are formed is not particularly limited, and can be R 801 ~R 808a possible position of the group.
[2883] In one embodiment, the compound represented by General Formula (8) above is represented by any one of General Formulae (81-1) to (81-6) below.
[2884] [Chemical Formula 469]
[2885]
[2886] [Chemical Formula 470]
[2887]
[2888] [Chemical Formula 471]
[2889]
[2890] (in General Formulae (81-1) to (81-6) above,
[2891] X8is the same as the meaning of X8in General Formula (8) above,
[2892] R 801 to R 824 of which at least 2 are monovalent groups represented by General Formula (84) above,
[2893] R 801 to R 824 each independently is
[2894] a hydrogen atom,
[2895] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[2896] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[2897] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,
[2898] a substituted or unsubstituted cyclic alkyl group having a ring-forming carbon number of 3 to 50,
[2899] a group represented by -Si(R 901 )(R 902 )(R 903 ),
[2900] a group represented by -O-(R 904 ),
[2901] a group represented by -S-(R 905 ),
[2902] a group represented by -N(R 906 )(R 907a group represented by the formula (a-1) shown below,
[2903] a halogen atom,
[2904] a cyano group,
[2905] a nitro group,
[2906] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or
[2907] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
[2908] In one embodiment, the compound represented by the above formula (8) is represented by any one of the following formulas (81-7) to (81-18).
[2909] [Chemical Formula 472]
[2910]
[2911] [Chemical Formula 473]
[2912]
[2913] [Chemical Formula 474]
[2914]
[2915] [Chemical Formula 475]
[2916]
[2917] [Chemical Formula 476]
[2918]
[2919] [Chemical Formula 477]
[2920]
[2921] (in the above formulas (81-7) to (81-18),
[2922] X8has the same meaning as X8in the above formula (8),
[2923] * is a single bond to a monovalent group represented by the above formula (84),
[2924] R 801 ~R 824 each independently has the same meaning as R 801 ~R 824 in the above formulas (81-1) to (81-6) other than the monovalent group represented by the above formula (84).
[2925] R not forming a divalent group represented by General Formula (82) and General Formula (83) and not being a monovalent group represented by General Formula (84) above 801 ~R 808 , and R not being a monovalent group represented by General Formula (84) above 811 ~R 814 and R 821 ~R 824 each independently is preferably
[2926] a hydrogen atom,
[2927] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[2928] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[2929] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,
[2930] a substituted or unsubstituted cyclic alkyl group having a ring-constituting carbon number of 3 to 50,
[2931] a substituted or unsubstituted aryl group having a ring-constituting carbon number of 6 to 50, or
[2932] a substituted or unsubstituted heterocyclic group having a ring-constituting atom number of 5 to 50.
[2933] The monovalent group represented by General Formula (84) above is preferably represented by General Formula (85) or General Formula (86) below.
[2934]
Chemical Formula 478
[2935]
[2936] (In General Formula (85) above,
[2937] R 831 ~R 840 each independently is preferably
[2938] a hydrogen atom,
[2939] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[2940] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[2941] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,
[2942] a substituted or unsubstituted cyclic alkyl group having a ring-constituting carbon number of 3 to 50,
[2943] a group represented by -Si(R 901 )(R 902 )(R 903 ),
[2944] -O-(R 904 ),
[2945] -S-(R 905 ),
[2946] -N(R 906 )(R 907 ),
[2947] a halogen atom,
[2948] a cyano group,
[2949] a nitro group,
[2950] a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms, or
[2951] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,
[2952] the * in the above formula (85) has the same meaning as the * in the above formula (84).
[2953]
Chemical Formula 479
[2954]
[2955] (in the above formula (86),
[2956] Ar 801 , L 801 and L 803 have the same meanings as Ar 801 , L 801 and L 803 in the above formula (84),
[2957] HAr 801 is a structure represented by the following formula (87).
[2958]
Chemical Formula 480
[2959]
[2960] (in the above formula (87),
[2961] X 81 is an oxygen atom or a sulfur atom,
[2962] any one of R 841 to R 848 is a single bond to L 803 ,
[2963] R 841 to R848 each independently is
[2964] a hydrogen atom,
[2965] substituted or unsubstituted alkyl having a carbon number of 1 to 50,
[2966] substituted or unsubstituted alkenyl having a carbon number of 2 to 50,
[2967] substituted or unsubstituted alkynyl having a carbon number of 2 to 50,
[2968] substituted or unsubstituted cycloalkyl having a ring-forming carbon number of 3 to 50,
[2969] -Si(R 901 )(R 902 )(R 903 ) group,
[2970] -O-(R 904 ) group,
[2971] -S-(R 905 ) group,
[2972] -N(R 906 )(R 907 ) group,
[2973] a halogen atom,
[2974] a cyano group,
[2975] a nitro group,
[2976] substituted or unsubstituted aryl having a ring-forming carbon number of 6 to 50, or
[2977] substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50.
[2978] As the compound represented by the above general formula (8), a compound described in International Publication No. 2014 / 104144, and, for example, a compound represented by the following formulae can be given as specific examples.
[2979]
Chemical Formula 481
[2980]
[2981]
Chemical Formula 482
[2982]
[2983]
Chemical Formula 483
[2984]
[2985]
Chemical Formula 484
[2986]
[2987] [Chemical Formula 485]
[2988]
[2989] [Chemical Formula 486]
[2990]
[2991] (compound represented by General Formula (9))
[2992] A compound represented by General Formula (9) will be described.
[2993] [Chemical Formula 487]
[2994]
[2995] (in the above General Formula (9),
[2996] A 91 ring and A 92 each of the rings is independently
[2997] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or
[2998] a substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms,
[2999] selected from A 91 ring and A 92 one or more of the rings in the ring
[3000] bonded to a structure represented by General Formula (92) below.
[3001] [Chemical Formula 488]
[3002]
[3003] (in the above General Formula (92),
[3004] A 93 ring is
[3005] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or
[3006] a substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms,
[3007] X9is NR 93 , C(R 94 )(R 95 ), Si(R 96 )(R97 ), Ge(R 98 ), Ge(R 99 ), an oxygen atom, a sulfur atom, or a selenium atom,
[3008] R 91 and R 92
[3009] are bonded to each other to form a substituted or unsubstituted monocyclic,
[3010] are bonded to each other to form a substituted or unsubstituted fused ring, or
[3011] are not bonded to each other,
[3012] R 91 and R 92 , and R 93 to R 99 are each independently
[3013] a hydrogen atom,
[3014] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[3015] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[3016] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,
[3017] a substituted or unsubstituted cyclic alkyl group having a ring-forming carbon number of 3 to 50,
[3018] a group represented by -Si(R 901 )(R 902 )(R 903 ),
[3019] a group represented by -O-(R 904 ),
[3020] a group represented by -S-(R 905 ),
[3021] a group represented by -N(R 906 )(R 907 ),
[3022] a halogen atom,
[3023] a cyano group,
[3024] a nitro group,
[3025] a substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50, or
[3026] a substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50.
[3027] one or both of the rings is selected from A 91 one or both of the rings is selected from A 92 one or both of the rings is selected from A 91 one or both of the rings is selected from A 92 one or both of the rings is selected from A
[3028] one or both of the rings is selected from A 91 one or both of the rings is selected from A 92 one or both of the rings is selected from A
[3029]
Chemical Formula 489
[3030]
[3031] one or both of the rings is selected from A
[3032] Ar 91 one or both of the rings is selected from A 92 each independently is
[3033] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or
[3034] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,
[3035] L 91 L 93 each independently is
[3036] a single bond,
[3037] a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms,
[3038] a substituted or unsubstituted bivalent heterocyclic group having 5 to 30 ring-forming atoms, or
[3039] a bivalent linking group formed by bonding of 2 to 4 selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms and a substituted or unsubstituted bivalent heterocyclic group having 5 to 30 ring-forming atoms,
[3040] in the above formula (93) indicates a bonding position to A 91 one or both of the rings is selected from A 92 one or both of the rings is selected from A
[3041] one or both of the rings is selected from A 91In addition to the ring, there is A 92 The ring is bonded to the structure represented by the above-mentioned general formula (92) at a ring-forming carbon atom of the above-mentioned aromatic hydrocarbon ring or a ring-forming atom of the above-mentioned hetero ring. In this case, the structures represented by the above-mentioned general formula (92) can be the same or different from each other.
[3042] In one embodiment, R 91 and R 92 each independently is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbons.
[3043] In one embodiment, R 91 and R 92 are bonded to each other to form a fluorene structure.
[3044] In one embodiment, ring A 91 and ring A 92 each independently is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbons, for example, a substituted or unsubstituted benzene ring.
[3045] In one embodiment, ring A 93 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbons, for example, a substituted or unsubstituted benzene ring.
[3046] In one embodiment, X9is an oxygen atom or a sulfur atom.
[3047] As the compound represented by the above-mentioned general formula (9), for example, the following compounds represented by the following general formulae can be given as specific examples.
[3048] [Chemical Formula 490]
[3049]
[3050] [Chemical Formula 491]
[3051]
[3052] [Chemical Formula 492]
[3053]
[3054] [Chemical Formula 493]
[3055]
[3056] (Compound represented by general formula (10))
[3057] The compound represented by general formula (10) will be described.
[3058] [Chemical Formula 494]
[3059]
[3060] [Chemical Formula 495]
[3061]
[3062] (in General Formula (10) above,
[3063] Ax1ring is a ring represented by General Formula (10a) above, which is fused at any position of the adjacent ring,
[3064] Ax2ring is a ring represented by General Formula (10b) above, which is fused at any position of the adjacent ring,
[3065] 2* in General Formula (10b) above is bonded to any position of Ax3ring,
[3066] X A and X B are each independently C(R 1003 )(R 1004 ), Si(R 1005 )(R 1006 ), an oxygen atom, or a sulfur atom,
[3067] Ax3ring is
[3068] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or
[3069] a substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms,
[3070] Ar 1001 is
[3071] a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms, or
[3072] a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms,
[3073] R 1001 to R 1006 are each independently
[3074] a hydrogen atom,
[3075] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
[3076] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
[3077] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
[3078] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
[3079] -Si(R 901) a group represented by the formula of -O-(R 902 ) a group represented by the formula of -O-(R 903 ) a group represented by the formula of -O-(R
[3080] ) a group represented by the formula of -O-(R 904 ) a group represented by the formula of -O-(R
[3081] ) a group represented by the formula of -O-(R 905 ) a group represented by the formula of -O-(R
[3082] ) a group represented by the formula of -O-(R 906 ) a group represented by the formula of -O-(R 907 ) a group represented by the formula of -O-(R
[3083] a halogen atom,
[3084] a cyano group,
[3085] a nitro group,
[3086] a substituted or unsubstituted aromatic group having a ring-constituting carbon number of 6 to 50, or
[3087] a substituted or unsubstituted heterocyclic group having a ring-constituting atom number of 5 to 50,
[3088] mx1 is 3, and mx2 is 2,
[3089] a plurality of R 1001 are the same or different from each other,
[3090] a plurality of R 1002 are the same or different from each other,
[3091] ax is 0, 1, or 2,
[3092] in the case where ax is 0 or 1, the structures within the parentheses represented by "3-ax" are the same or different from each other,
[3093] in the case where ax is 2, a plurality of Ar 1001 are the same or different from each other.
[3094] in one embodiment, Ar 1001 is a substituted or unsubstituted aromatic group having a ring-constituting carbon number of 6 to 50.
[3095] in one embodiment, the Ax3 ring is a substituted or unsubstituted aromatic hydrocarbon ring having a ring-constituting carbon number of 6 to 50, for example, a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted anthracene ring.
[3096] in one embodiment, R 1003 and R 1004 are each independently a substituted or unsubstituted alkyl group having a carbon number of 1 to 50.
[3097] in one embodiment, ax is 1.
[3098] As the compound represented by the above general formula (10), for example, the following compounds can be mentioned as specific examples.
[3099]
Chemical Formula 496
[3100]
[3101] In one embodiment, in the light-emitting layer described above, as the compound of at least one of the third compound and the fourth compound, one or more compounds selected from the group consisting of
[3102] the compound represented by the above general formula (4),
[3103] the compound represented by the above general formula (5),
[3104] the compound represented by the above general formula (7),
[3105] the compound represented by the above general formula (8),
[3106] the compound represented by the above general formula (9), and
[3107] one or more compounds selected from the group consisting of the compounds represented by the above general formula (63a).
[3108]
Chemical Formula 497
[3109]
[3110] (in the above general formula (63a),
[3111] R 631 and R 646 may be bonded to form a substituted or unsubstituted heterocycle, or may not form a substituted or unsubstituted heterocycle.
[3112] R 633 and R 647 may be bonded to form a substituted or unsubstituted heterocycle, or may not form a substituted or unsubstituted heterocycle.
[3113] R 634 and R 651 may be bonded to form a substituted or unsubstituted heterocycle, or may not form a substituted or unsubstituted heterocycle.
[3114] R 641 and R 642 may be bonded to form a substituted or unsubstituted heterocycle, or may not form a substituted or unsubstituted heterocycle.
[3115] R 631 to R 651 may be bonded to form a substituted or unsubstituted heterocycle, or may not form a substituted or unsubstituted heterocycle.
[3116] which are bonded to each other to form a substituted or unsubstituted monocyclic ring,
[3117] which are bonded to each other to form a substituted or unsubstituted fused ring, or
[3118] which are not bonded to each other,
[3119] R which does not form the above-mentioned substituted or unsubstituted heterocyclic ring, does not form the above-mentioned substituted or unsubstituted monocyclic ring, and does not form the above-mentioned substituted or unsubstituted fused ring, 631 ~R 651 each independently is
[3120] a hydrogen atom,
[3121] a halogen atom,
[3122] a cyano group,
[3123] a nitro group,
[3124] a substituted or unsubstituted alkyl group having a carbon number of 1 to 50,
[3125] a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50,
[3126] a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50,
[3127] a substituted or unsubstituted cyclic alkyl group having a ring-forming carbon number of 3 to 50,
[3128] -Si(R 901 )(R 902 )(R 903 ) group,
[3129] an -O-(R 904 ) group,
[3130] an -S-(R 905 ) group,
[3131] an -N(R 906 )(R 907 ) group,
[3132] a substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50, or a substituted or unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50,
[3133] wherein R 631 ~R 651 among the above-mentioned substituted or unsubstituted heterocyclic ring, the above-mentioned substituted or unsubstituted monocyclic ring, and the above-mentioned substituted or unsubstituted fused ring is
[3134] a halogen atom,
[3135] a cyano group,
[3136] a nitro group,
[3137] a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 50,
[3138] a substituted or unsubstituted alkenyl group having a carbon atom number of 2 to 50,
[3139] a substituted or unsubstituted alkynyl group having a carbon atom number of 2 to 50,
[3140] a substituted or unsubstituted cyclic alkyl group having a ring-constituting carbon atom number of 3 to 50,
[3141] a group represented by -Si(R 901 )(R 902 )(R 903 ),
[3142] a group represented by -O-(R 904 ),
[3143] a group represented by -S-(R 905 ),
[3144] a group represented by -N(R 906 )(R 907 ),
[3145] a halogen atom,
[3146] a cyano group,
[3147] a nitro group,
[3148] a substituted or unsubstituted aryl group having a ring-constituting carbon atom number of 6 to 50, or
[3149] a substituted or unsubstituted heterocyclic group having a ring-constituting atom number of 5 to 50.
[3150] In one embodiment, the compound represented by General Formula (4) is a compound represented by General Formula (41-3), General Formula (41-4), or General Formula (41-5), and the A1ring in General Formula (41-5) is a substituted or unsubstituted fused aromatic hydrocarbon ring having a ring-constituting carbon atom number of 10 to 50 or a substituted or unsubstituted fused heterocyclic ring having a ring-constituting atom number of 8 to 50.
[3151] In one embodiment, the substituted or unsubstituted fused aromatic hydrocarbon ring having a ring-constituting carbon atom number of 10 to 50 in General Formula (41-3), General Formula (41-4), and General Formula (41-5) is
[3152] a substituted or unsubstituted naphthalene ring,
[3153] a substituted or unsubstituted anthracene ring, or
[3154] a substituted or unsubstituted fluorene ring,
[3155] The substituted or unsubstituted condensed heterocyclic ring having 8 to 50 ring-forming atoms is
[3156] a substituted or unsubstituted dibenzofuran ring,
[3157] a substituted or unsubstituted carbazole ring, or
[3158] a substituted or unsubstituted dibenzothiophene ring.
[3159] In one embodiment, the substituted or unsubstituted condensed aromatic hydrocarbon ring having 10 to 50 ring-forming carbons in General Formula (41-3), General Formula (41-4), or General Formula (41-5) above is
[3160] a substituted or unsubstituted naphthalene ring, or
[3161] a substituted or unsubstituted fluorene ring,
[3162] The substituted or unsubstituted condensed heterocyclic ring having 8 to 50 ring-forming atoms is
[3163] a substituted or unsubstituted dibenzofuran ring,
[3164] a substituted or unsubstituted carbazole ring, or
[3165] a substituted or unsubstituted dibenzothiophene ring.
[3166] In one embodiment, the compound represented by General Formula (4) above is selected from the group consisting of
[3167] a compound represented by General Formula (461) below,
[3168] a compound represented by General Formula (462) below,
[3169] a compound represented by General Formula (463) below,
[3170] a compound represented by General Formula (464) below,
[3171] a compound represented by General Formula (465) below,
[3172] a compound represented by General Formula (4660 below, and
[3173] a compound represented by General Formula (467) below.
[3174] [Chemical Formula 498]
[3175]
[3176] [Chemical Formula 499]
[3177]
[3178] [Chemical Formula 500]
[3179]
[3180] [Chemical Formula 501]
[3181]
[3182] [Chemical Formula 502]
[3183]
[3184] (in General Formulas (461) to (467) above,
[3185] one group selected from the group consisting of R 421 , R 427 , R 431 , R 436 , R 440 , R 448 , and R 451 , and R 454 two or more adjacent groups selected from the group consisting of R
[3186] are bonded to each other to form a substituted or unsubstituted monocyclic ring,
[3187] are bonded to each other to form a substituted or unsubstituted fused ring, or
[3188] are not bonded to each other,
[3189] R 437 , R 438 , and R 421 which do not form the above-mentioned substituted or unsubstituted monocyclic ring and do not form the above-mentioned substituted or unsubstituted fused ring 427 , R 431 , R 436 , R 440 , R 448 , and R 451 , and R 454 are each independently
[3190] a hydrogen atom,
[3191] a substituted or unsubstituted alkyl group with a carbon number of 1 to 50,
[3192] a substituted or unsubstituted alkenyl group with a carbon number of 2 to 50,
[3193] a substituted or unsubstituted alkynyl group with a carbon number of 2 to 50,
[3194] a substituted or unsubstituted cyclic alkyl group with a ring-constituting carbon number of 3 to 50,
[3195] -Si(R 901 )(R 902(R) 903 The groups shown in the figure,
[3196] -O-(R 904 The groups shown in the figure,
[3197] -S-(R 905 The groups shown in the figure,
[3198] -N(R 906 (R) 907 The groups shown in the figure,
[3199] Halogen atoms,
[3200] cyano,
[3201] Nitro,
[3202] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[3203] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[3204] X4 represents an oxygen atom, NR 801 Or C(R) 802 (R) 803 ),
[3205] R 801 R 802 and R 803 Each independently
[3206] hydrogen atom,
[3207] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[3208] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[3209] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[3210] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[3211] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[3212] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[3213] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[3214] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.
[3215] In R 803 In the case of multiple Rs, multiple Rs 803 (They may be the same or different.)
[3216] In one implementation, R 421 ~R 427 and R 440 ~R 448 Each independently
[3217] hydrogen atom,
[3218] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[3219] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[3220] In one implementation, R 421 ~R 427 and R 440 ~R 447 Each independently chooses freedom
[3221] hydrogen atom,
[3222] Substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, and
[3223] The group consisting of substituted or unsubstituted heterocyclic groups with 5 to 18 cyclic atoms.
[3224] In one embodiment, the compound represented by the above general formula (41-3) is the compound represented by the following general formula (41-3-1).
[3225]
Chemical Formula 503
[3226]
[3227] (In the above general formula (41-3-1), R) 423 R 425 R 426 R 442 R 444 and R 445 Each independently relates to R in the above general formula (41-3). 423 R 425 R 426 R 442 R 444 and R 445 The meaning is the same.
[3228] In one embodiment, the compound represented by the above general formula (41-3) is the compound represented by the following general formula (41-3-2).
[3229] [Chemical Formula 504]
[3230]
[3231] (In the above general formula (41-3-2), R 421 ~R 427 and R 440 ~R 448 each independently have the same meaning as R 421 ~R 427 and R 440 ~R 448 in the above general formula (41-3),
[3232] wherein at least one of R 421 ~R 427 and R 440 ~R 446 is a group represented by -N(R 906 )(R 907 ).
[3233] In one embodiment, any two of R 421 ~R 427 and R 440 ~R 446 in the above general formula (41-3-2) are groups represented by -N(R 906 )(R 907 ).
[3234] In one embodiment, the compound represented by the above general formula (41-3-2) is a compound represented by the following general formula (41-3-3).
[3235]
Chemical Formula 505
[3236]
[3237] (In the above general formula (41-3-3), R 421 ~R 424 , R 440 ~R 443 , R 447 and R 448 each independently have the same meaning as R 421 ~R 424 , R 440 ~R 443 , R 447 and R 448 in the above general formula (41-3),
[3238] R A , R B , R C and R D each independently are
[3239] substituted or unsubstituted aryl having 6 to 18 ring-forming carbon atoms, or
[3240] substituted or unsubstituted heterocyclic group having 5 to 18 ring-forming atoms.
[3241] In one embodiment, the compound represented by the above formula (41-3-3) is a compound represented by the following formula (41-3-4).
[3242] [Chemical Formula 506]
[3243]
[3244] (In the above formula (41-3-4), R 447 , R 448 , R A , R B , R C , and R D each independently have the same meaning as R 447 , R 448 , R A , R B , R C , and R D in the above formula (41-3-3).
[3245] In one embodiment, R A , R B , R C , and R D each independently is a substituted or unsubstituted aryl having 6 to 18 ring-forming carbon atoms.
[3246] In one embodiment, R A , R B , R C , and R D each independently is a substituted or unsubstituted phenyl group.
[3247] In one embodiment, R 447 , and R 448 is a hydrogen atom.
[3248] In one embodiment, the substituent when the expression "substituted or unsubstituted" in the above formulae is
[3249] unsubstituted alkyl group having 1 to 50 carbon atoms,
[3250] unsubstituted alkenyl group having 2 to 50 carbon atoms,
[3251] unsubstituted alkynyl group having 2 to 50 carbon atoms,
[3252] unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
[3253] -Si(R 901a (R) 902a (R) 903a ),
[3254] -O-(R 904a ),
[3255] -S-(R 905a ),
[3256] -N(R 906a (R) 907a ),
[3257] Halogen atoms,
[3258] cyano,
[3259] Nitro,
[3260] Unsubstituted aryl groups with 6 to 50 carbon atoms, or
[3261] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms
[3262] R 901a ~R 907a Each independently
[3263] hydrogen atom,
[3264] Unsubstituted alkyl groups having 1 to 50 carbon atoms
[3265] Unsubstituted aryl groups with 6 to 50 carbon atoms, or
[3266] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms
[3267] In R 901a When there are more than two, R is more than two. 901a They are the same or different.
[3268] In R 902a When there are more than two, R is more than two. 902a They are the same or different.
[3269] In R 903a When there are more than two, R is more than two. 903a They are the same or different.
[3270] In R 904a When there are more than two, R is more than two. 904a They are the same or different.
[3271] In R 905a When there are more than two, R is more than two.905a are the same as or different from each other,
[3272] in R 906a in the case where two or more exist, two or more of R 906a are the same as or different from each other,
[3273] in R 907a in the case where two or more exist, two or more of R 907a are the same as or different from each other.
[3274] in the case where the expression "substituted or unsubstituted" in each of the above formulae is substituted, the substituent is
[3275] unsubstituted alkyl having a carbon number of 1 to 50,
[3276] unsubstituted aryl having a ring-forming carbon number of 6 to 50, or
[3277] unsubstituted heterocyclic group having a ring-forming atom number of 5 to 50.
[3278] in the case where the expression "substituted or unsubstituted" in each of the above formulae is substituted, the substituent is
[3279] unsubstituted alkyl having a carbon number of 1 to 18,
[3280] unsubstituted aryl having a ring-forming carbon number of 6 to 18, or
[3281] unsubstituted heterocyclic group having a ring-forming atom number of 5 to 18.
[3282] In the organic EL element according to the present embodiment, it is preferable that the first light-emitting layer further contain a third compound having a fluorescent light-emitting property, and the third compound be a compound that shows light emission with a peak wavelength of a main peak of 430 nm or more and 480 nm or less.
[3283] In the organic EL element according to the present embodiment, it is preferable that the second light-emitting layer further contain a fourth compound having a fluorescent light-emitting property, and the fourth compound be a compound that shows light emission with a peak wavelength of a main peak of 430 nm or more and 480 nm or less.
[3284] The method for measuring the peak wavelength of a main peak of a compound is as follows. A 10 - 6 mL or more and 10 -5 mL or less of a toluene solution is prepared and added to a quartz cuvette, and the luminescence spectrum of the sample is measured at normal temperature (300 K) (the vertical axis is set to the luminescence intensity, and the horizontal axis is set to the wavelength). The luminescence spectrum can be measured by a spectrophotometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the luminescence spectrum measuring device is not limited to the device used here.
[3285] In the emission spectrum, the peak wavelength of the emission spectrum in which the emission intensity is the largest is taken as the emission main peak peak wavelength. Note that, in this specification, the main peak peak wavelength is sometimes referred to as a fluorescence emission main peak peak wavelength (FL-peak).
[3286] In the organic EL element according to the present embodiment, in the case where the first light-emitting layer contains the first compound and the third compound, the first compound is preferably a host material (sometimes referred to as a matrix material), and the third compound is preferably a dopant material (sometimes referred to as a guest material, an emitter, or a light-emitting material).
[3287] In the organic EL element according to the present embodiment, in the case where the first light-emitting layer contains the first compound and the third compound, the singlet energy S1(H1) of the first compound and the singlet energy S1(D3) of the third compound preferably satisfy the following mathematical expression (Mathematical Expression 1).
[3288] S1(H1) > S1(D3)... (Mathematical Expression 1)
[3289] In the organic EL element according to the present embodiment, in the case where the second light-emitting layer contains the second compound and the fourth compound, the second compound is preferably a host material (sometimes referred to as a matrix material), and the fourth compound is preferably a dopant material (sometimes referred to as a guest material, an emitter, or a light-emitting material).
[3290] In the organic EL element according to the present embodiment, in the case where the second light-emitting layer contains the second compound and the fourth compound, the singlet energy S1(H2) of the second compound and the singlet energy S1(D4) of the fourth compound preferably satisfy the following mathematical expression (Mathematical Expression 2).
[3291] S1(H2) > S1(D4)... (Mathematical Expression 2)
[3292] (Singlet Energy S1)
[3293] As a method for measuring the singlet energy S1 using a solution (sometimes referred to as a solution method), the following method can be given.
[3294] A toluene solution of the compound to be measured at 10 -5 mol / L or more and 10 -4 mol / L or less was prepared and added to a quartz cuvette, and the absorption spectrum of the sample was measured at normal temperature (300 K) (the vertical axis was set to the absorption intensity, and the horizontal axis was set to the wavelength). The wavelength value λedge [nm] of the intersection of the tangent line with respect to the drop on the long wavelength side of the absorption spectrum and the horizontal axis was substituted into the conversion formula (F2) shown below, and the singlet energy was calculated.
[3295] Conversion formula (F2): S1 [eV] = 1239.85 / λedge
[3296] As the absorption spectrum measuring device, for example, a spectrophotometer (device name: U3310) manufactured by Hitachi, Ltd. can be given, but the present application is not limited thereto.
[3297] A tangent line to the fall on the long wavelength side of the absorption spectrum is drawn as follows. When moving on the spectrum curve in the long wavelength direction from the maximum on the long wavelength side among the maxima of the absorption spectrum, the tangent line at each point on the curve is considered. The tangent line decreases in slope repeatedly and then increases as the curve falls (i.e., as the value of the vertical axis decreases). The tangent line drawn at the point where the value of the slope takes a minimum value on the long wavelength side (excluding the case where the absorbance is 0.1 or less) is taken as the tangent line to the fall on the long wavelength side of the absorption spectrum.
[3298] Note that the maximum point where the value of the absorbance is 0.2 or less is not included in the above-mentioned maximum on the long wavelength side.
[3299] In the organic EL element according to the present embodiment, it is also preferable that the electron mobility μH1 of the first compound and the electron mobility μH2 of the second compound satisfy the following mathematical formula (Mathematical Formula 3).
[3300] μH2 > μH1... (Mathematical Formula 3)
[3301] By the first compound and the second compound satisfying the above-mentioned mathematical formula (Mathematical Formula 3), the recombination ability of holes and electrons in the first light-emitting layer is improved.
[3302] The electron mobility can be measured using an impedance spectroscopy method by the following method.
[3303] A measurement target layer having a thickness of 100 nm to 200 nm is clamped with an anode and a cathode, and a small alternating voltage of 100 mV or less is applied while a bias DC voltage is applied. The value (absolute value and phase) of the alternating current flowing at this time is measured. This measurement is performed while changing the frequency of the alternating voltage, and the complex impedance (Z) is calculated from the current value and the voltage value. The frequency dependence of the imaginary part (ImM) of the modulus M = iωZ (i: imaginary unit, ω: angular frequency) is obtained at this time, and the reciprocal of the frequency ω at which ImM takes a maximum value is defined as the response time of the electron conducting within the measurement target layer. Then, the electron mobility is calculated by the following formula.
[3304] Electron mobility = (film thickness of measurement target layer) 2 / (response time · voltage)
[3305] The first light-emitting layer and the second light-emitting layer preferably do not contain a phosphorescent light-emitting material (dopant material).
[3306] In addition, the first light-emitting layer and the second light-emitting layer preferably do not contain a heavy metal complex and a phosphorescent light-emitting rare earth metal complex. Here, as the heavy metal complex, for example, iridium complexes, osmium complexes, and platinum complexes, and the like can be given.
[3307] In addition, the first light-emitting layer and the second light-emitting layer also preferably do not contain a metal complex.
[3308] (Film thickness of light-emitting layer)
[3309] The film thickness of the light-emitting layer of the organic EL element according to the present embodiment is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and further preferably 10 nm or more and 50 nm or less. If the film thickness of the light-emitting layer is 5 nm or more, the light-emitting layer is easily formed, and the chromaticity is easily adjusted. If the film thickness of the light-emitting layer is 50 nm or less, the increase in driving voltage is easily suppressed.
[3310] (Content ratio of compound in light-emitting layer)
[3311] In the case where the first light-emitting layer contains the first compound and the third compound, the content ratio of the first compound and the third compound in the first light-emitting layer is, for example, each preferably in the following range.
[3312] The content ratio of the first compound is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and further preferably 95% by mass or more and 99% by mass or less.
[3313] The content ratio of the third compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and further preferably 1% by mass or more and 5% by mass or less.
[3314] The upper limit of the total content ratio of the first compound and the third compound in the first light-emitting layer is 100% by mass.
[3315] Note that the present embodiment does not exclude the inclusion of a material other than the first compound and the third compound in the first light-emitting layer.
[3316] In the first light-emitting layer, the first compound can contain only one kind, or can contain two or more kinds. In the first light-emitting layer, the third compound can contain only one kind, or can contain two or more kinds.
[3317] In the case where the second light-emitting layer contains the second compound and the fourth compound, the content ratio of the second compound and the fourth compound in the second light-emitting layer is, for example, each preferably in the following range.
[3318] The content ratio of the second compound is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and further preferably 95% by mass or more and 99% by mass or less.
[3319] The content ratio of the fourth compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and further preferably 1% by mass or more and 5% by mass or less.
[3320] The upper limit of the total content ratio of the second compound and the fourth compound in the second light-emitting layer is 100% by mass.
[3321] Note that the present embodiment does not exclude the inclusion of a material other than the second compound and the fourth compound in the second light-emitting layer.
[3322] The second compound can include only one kind or two or more kinds in the second light-emitting layer. The fourth compound can include only one kind or two or more kinds in the second light-emitting layer.
[3323] Further description is made on the constitution of the organic EL element. Hereinafter, the description of symbols is sometimes omitted.
[3324] (Substrate)
[3325] A substrate is used as a support of the organic EL element. As the substrate, for example, glass, quartz, plastic, and the like can be used. In addition, a flexible substrate can be used. The flexible substrate refers to a substrate that can be bent (flexible). For example, a plastic substrate or the like can be given. As a material for forming a plastic substrate, for example, polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, polyethylene naphthalate, and the like can be given. In addition, an inorganic vapor deposition film can be used.
[3326] (Anode)
[3327] The anode formed on the substrate preferably uses a metal, an alloy, a conductive compound, and a mixture thereof, or the like having a large work function (specifically, 4.0 eV or more). Specifically, for example, indium-tin oxide (ITO), indium-tin oxide containing silicon or silicon oxide, indium-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, graphene, and the like can be given. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or a nitride of a metal material (for example, titanium nitride), and the like can be given.
[3328] These materials are generally formed into films by a sputtering method. For example, indium oxide-zinc oxide can be formed by using a target in which zinc oxide is added to indium oxide at 1% by mass or more and 10% by mass or less, using a sputtering method. Also, for example, indium oxide containing tungsten oxide and zinc oxide can be formed by using a target in which 0.5% by mass or more and 5% by mass or less of tungsten oxide and 0.1% by mass or more and 1% by mass or less of zinc oxide are contained in indium oxide, using a sputtering method. Also, it can be produced by a vacuum evaporation method, a coating method, an inkjet method, a spin coating method, or the like.
[3329] Among the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that easily injects holes regardless of the work function of the anode, and thus a material that can be used as an electrode material (for example, a metal, an alloy, a conductive compound, and a mixture thereof, and also including an element belonging to Group 1 or Group 2 of the periodic table) can be used.
[3330] An element belonging to Group 1 or Group 2 of the periodic table, that is, an alkali metal such as lithium (Li) and cesium (Cs), and an alkaline earth metal such as magnesium (Mg), calcium (Ca), and strontium (Sr), and an alloy containing the same (for example, MgAg, AlLi), a rare earth metal such as europium (Eu) and ytterbium (Yb), and an alloy containing the same, and the like, which are materials having a small work function, can also be used. Note that when the anode is formed using an alkali metal, an alkaline earth metal, and an alloy containing the same, a vacuum evaporation method, a sputtering method, or the like can be used. In addition, when silver paste or the like is used, a coating method, an inkjet method, or the like can be used.
[3331] (cathode)
[3332] The cathode preferably uses a metal, an alloy, a conductive compound, and a mixture thereof, or the like, which have a small work function (specifically, 3.8 eV or less). As specific examples of such a cathode material, an element belonging to Group 1 or Group 2 of the periodic table, that is, an alkali metal such as lithium (Li) and cesium (Cs), and an alkaline earth metal such as magnesium (Mg), calcium (Ca), and strontium (Sr), and an alloy containing the same (for example, MgAg, AlLi), a rare earth metal such as europium (Eu) and ytterbium (Yb), and an alloy containing the same, and the like, can be given.
[3333] Note that when the cathode is formed using an alkali metal, an alkaline earth metal, and an alloy containing the same, a vacuum evaporation method, a sputtering method, or the like can be used. In addition, when silver paste or the like is used, a coating method, an inkjet method, or the like can be used.
[3334] Note that by providing the electron injection layer, a cathode can be formed using various conductive materials such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, and the like, regardless of the work function. These conductive materials can be deposited by a sputtering method, an inkjet method, a spin coating method, or the like.
[3335] (hole injection layer)
[3336] The hole injection layer is a layer containing a substance having high hole injectability. As the substance having high hole injectability, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, and the like can be used.
[3337] In addition, as the substance having high hole injectability, 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), and the like, aromatic amine compounds, and the like, 2,3,6,7,10,11-hexacyanodipyrazino[2,3-f:20,30-h]quinoxaline (abbreviation: HAT-CN) can be given.
[3338] In addition, as a substance having high hole-injection property, a high molecular compound (oligomer, dendrimer, polymer, etc.) can also be used. For example, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl) methacrylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD), and the like can be given. In addition, a high molecular compound to which an acid is added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly(styrenesulfonic acid) (PAni / PSS), and the like can be used.
[3339] (Hole transport layer)
[3340] The hole transport layer is a layer containing a substance having high hole-transport property. As the substance having high hole-transport property, an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used. Specifically, 4,4'-bis[N-(l-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[l,l'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), and the like can be given. The substance described here is mainly a substance having a hole mobility of 10 -6 cm 2 or more.
[3341] As the substance having high hole-transport property, an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used. Specifically, 4,4'-bis[N-(l-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[l,l'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), and the like can be given. The substance described here is mainly a substance having a hole mobility of 10
[3342] Note that as long as a substance having higher hole-transport property than electron-transport property is used, a substance other than these can also be used. Note that a layer containing a substance having high hole-transport property is not necessarily formed as a single layer, but can be formed as a stack of two or more layers formed of the above-described substance.
[3343] (electron-transport layer)
[3344] The electron-transport layer is a layer containing a substance having high electron-transport property. As the electron-transport layer, a metal complex such as an aluminum complex, a beryllium complex, and a zinc complex; a heteroaromatic compound such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative, and a phenanthroline derivative; and a high molecular compound can be used. Specifically, as an organic compound of a low molecule, an aluminum complex such as Alq3, tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), BAlq, Znq, ZnPBO, ZnBTZ, and the like can be used. In addition, a heteroaromatic compound such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs), and the like can be used. In this embodiment, a benzimidazole compound can be suitably used. The substances described here are mainly substances having an electron mobility of 10 -6 cm 2 (Vs) or higher. Note that as long as a substance having higher electron-transport property than hole-transport property is used, a substance other than the above can also be used as the electron-transport layer. The electron-transport layer can be formed of a single layer or can be formed of a stack of two or more layers containing the above-described substance.
[3345] As specific examples of the compound which can be used for the electron-transport layer, the following compounds can be given, for example. Note that the present application is not limited to these specific examples of the compounds.
[3346]
Chemical Formula 507
[3347]
[3348] In addition, a high molecular compound can also be used in the electron transport layer. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy), or the like can be used.
[3349] (Electron injection layer)
[3350] The electron injection layer is a layer containing a substanc...
Claims
1. A compound having at least one group represented by the following general formula (11) and containing only one benzoxanthene ring represented by the following general formula (1) in a molecule, in the general formula (1), consisting of 2 or more adjacent groups selected from R 10 ~R 19 groups are not bonded to each other, R 10 ~R 19 each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having a carbon number of 1 to 50, a substituted or unsubstituted cyclic alkyl group having a ring-forming carbon number of 3 to 50, a substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50, or the group represented by the general formula (11), wherein, R 10 ~R 19 at least one of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R in a case where a plurality of the groups represented by the general formula (11) are present, the plurality of the groups represented by the general formula (11) are the same as or different from each other, L1 is a substituted or unsubstituted arylene group having a ring-forming carbon number of 6 to 15, mx is 1, 2, or 3, in a case where two or more of L1 are present, the two or more of L1 are the same as or different from each other, Ar1 is a substituted or unsubstituted aryl group in which four or more benzene rings are fused, in a case where two or more of Ar1 are present, the two or more of Ar1 are the same as or different from each other, in the general formula (11) represents a bonding position, wherein the compound does not contain a cyano group in a molecule.
2. The compound according to claim 1, wherein the compound having at least one group represented by the general formula (11) and containing only one benzoxanthene ring represented by the general formula (1) in a molecule is represented by the following general formula (121) or general formula (122), in the general formula (121) and general formula (122), R 10 ~R 19 each independently of the other R 10 ~R 19 have the same meaning, Ar1, L1, and mx have the same meanings as those in the general formula (11), respectively.
3. The compound according to claim 2, wherein In the general formula (121), R 10 ~R 12 , R 14 ~R 19 is not the group shown in the general formula (11).
4. The compound according to claim 2, wherein In the general formula (122), R 10 ~R 17 , R 19 is not the group shown in the general formula (11).
5. The compound according to claim 1, wherein R of the group represented by the general formula (11) 10 ~R 19 each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having a carbon number of 1 to 20, a substituted or unsubstituted cyclic alkyl group having a ring-forming carbon number of 3 to 20, or a substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 30.
6. The compound according to claim 5, wherein R is not a group represented by the general formula (11) 10 ~R 19 a hydrogen atom.
7. The compound according to claim 1, wherein Ar1 is a substituted or unsubstituted aryl group in which four benzene rings are fused.
8. The compound according to claim 1, wherein the compound having at least one group represented by the general formula (11) and containing only one benzoxanthene ring represented by the general formula (1) in a molecule is represented by the following general formula (123), general formula (124), general formula (125), or general formula (126), in the general formula (123), general formula (124), general formula (125), and general formula (126), X is an oxygen atom, L 10 To a substituted or unsubstituted arylene group having a ring-forming carbon number of 6 to 15, Ar 10 which is a substituted or unsubstituted aryl group having 4 or more condensed benzene rings, Ar 11 is a substituted or unsubstituted aromatic group having 6 to 14 ring-forming carbon atoms, wherein Ar 11 other than substituted or unsubstituted anthracenyl, m10 is 5, m11 is 6, Rm is each independently a hydrogen atom, a substituted or unsubstituted alkyl group having a carbon number of 1 to 50, a substituted or unsubstituted cyclic alkyl group having a ring-forming carbon number of 3 to 50, or a substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 50, a plurality of Rm are not bonded to each other.
9. The compound according to claim 8, wherein The compound represented by the general formula (123) is represented by the following general formula (1230), the compound represented by the general formula (124) is represented by the following general formula (1240), the compound represented by the general formula (125) is represented by the following general formula (1250), and the compound represented by the general formula (126) is represented by the following general formula (1260), in the general formula (1230), the general formula (1240), the general formula (1250), and the general formula (1260), X, L 10 , Ar 10 , Ar 11 , m10, m11 and Rmare each independently of the meanings of X, L 10 , Ar 10 , Ar 11 , m10, m11 and Rmare each independently of the meanings of X, L 10. A compound having at least one group represented by the following general formula (110A) and containing only one benzoxanthene ring represented by the following general formula (100A) in a molecule, in the general formula (100A), consisting of adjacent 2 or more selected from the group consisting of R 10 ~R 19 consisting of adjacent 2 or more selected from the group consisting of R R 10 ~R 19 each independently is a hydrogen atom, a substituted or unsubstituted alkyl group with a carbon number of 1 to 50, a substituted or unsubstituted cycloalkyl group with a ring-forming carbon number of 3 to 50, a substituted or unsubstituted aryl group with a ring-forming carbon number of 6 to 50, or the group represented by the general formula (110A), wherein, R 13 and at least one of R 18 is a group of the formula (110A) in the case where a plurality of groups represented by the general formula (110A) are present, the plurality of groups represented by the general formula (110A) are the same as or different from each other, L 100 To a single bond, or a substituted or unsubstituted arylene group with a ring-forming carbon number of 6 to 50, mx is 1, 2, or 3, In L 100 In case of 2 or more, the 2 or more L 100 are the same or different from each other, Ar1is a substituted or unsubstituted aryl group in which 4 or more benzene rings are fused, in the case where 2 or more Ar1s are present, the 2 or more Ar1s are the same as or different from each other, in the general formula (110A) represents a bonding position, wherein the compound does not contain a cyano group in a molecule.
11. The compound according to claim 10, wherein a compound having at least one group represented by the general formula (110A) and containing only one benzoxanthene ring represented by the general formula (100A) in a molecule is represented by the following general formula (121A) or general formula (122A), in the general formula (121A) and general formula (122A), R 10 ~R 19 each independently R 10 ~R 19 have the same meaning, Ar1, L 100 and mx have the same meaning as Ar1, L 100 and mx in the general formula (110A).
12. The compound according to claim 11, wherein in the general formula (121A), R 10 ~R 12 , R 14 ~R 19 is not a group represented by the general formula (110A).
13. The compound according to claim 11, wherein In the general formula (122A), R 10 ~R 17 , R 19 is not a group represented by the general formula (110A).
14. The compound according to claim 10, wherein R of the group represented by the general formula (110A) 10 ~R 19 each independently is a hydrogen atom, a substituted or unsubstituted alkyl group with a carbon number of 1 to 20, a substituted or unsubstituted cycloalkyl group with a ring-forming carbon number of 3 to 20, or a substituted or unsubstituted aryl group with a ring-forming carbon number of 6 to 30.
15. The compound according to claim 14, wherein R of the group represented by the general formula (110A) 10 ~R 19 is a hydrogen atom.
16. The compound according to claim 10, wherein L 100 is a single bond, or substituted or unsubstituted arylene including 3 or fewer phenyl rings.
17. The compound according to claim 16, wherein L 100 other than an anthrylene group which is substituted or unsubstituted.
18. The compound according to claim 16, wherein L 100 is a single bond.
19. The compound according to any one of claims 1 to 17, wherein - (L1) mx - the group represented by -L 10 - the group represented by -L 100 ) mx - the group represented by -L is a group represented by any one of General Formulae (111) to (120) in the above general formula (111) to general formula (120) indicates a bonding position.
20. The compound according to claim 19, wherein - (L1) mx - the group shown, -L 10 - the group shown or -(L 100 ) mx - the group shown is a group shown in the general formula (111) or (112).
21. The compound according to any one of claims 1 to 6 and 8 to 18, wherein Ar1or Ar 10 is an aryl group condensed with 4 substituted or unsubstituted benzene rings, or an aryl group condensed with 5 substituted or unsubstituted benzene rings.
22. The compound according to any one of claims 1 to 6 and 8 to 18, wherein Ar1or Ar 10 is a group of the following general formula (1100), (1200), (1300), (1400), (1500), (1600) or (1800), In the general formula (1100), R 111 ~R 120 one of them is a bond, In the general formula (1200), R 1201 ~R 1212 one of them is a bond, In the general formula (1300), R 1301 ~R 1314 one of them is a bond, In the general formula (1400), R 1401 ~R 1414 one of them is a bond, In the general formula (1500), R 1501 ~R 1514 one of them is a bond, In the general formula (1600), R 1601 ~R 1612 one of them is a bond, In the general formula (1800), R 1801 ~R 1812 one of them is a bond, R other than a bond 111 ~R 120 , R other than a bond 1201 ~R 1212 , R other than a bond 1301 ~R 1314 , R other than a bond 1401 ~R 1414 , R other than a bond 1501 ~R 1514 , R other than a bond 1601 ~R 1612 , and R other than a bond 1801 ~R 1812 each independently is a hydrogen atom, a substituted or unsubstituted alkyl group with a carbon number of 1 to 50, a substituted or unsubstituted halogenated alkyl group with a carbon number of 1 to 50, a substituted or unsubstituted alkenyl group with a carbon number of 2 to 50, a substituted or unsubstituted alkynyl group with a carbon number of 2 to 50, a substituted or unsubstituted cycloalkyl group with a ring-forming carbon number of 3 to 50, a substituted or unsubstituted aryl group with a ring-forming carbon number of 6 to 50. -Si(R 901 )(R 902 )(R 903 ) shown in the formula (1), -O-(R 904 ) a group represented by the formula: -S-(R 905 ) groups, -N(R 906 (R) 907 The groups shown in the figure, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 groups shown, -COOR 802 groups shown, a halogen atom, a nitro group, a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, Here, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, In R 901 In case of multiple, the multiple R 901 are the same or different from each other, In R 902 In case of multiple, the multiple R 902 are the same or different from each other, In R 903 In case of multiple R 903 are the same or different from each other, In R 904 In case of multiple R 904 are the same or different from each other, In R 905 In case of multiple R 905 are the same or different from each other, In R 906 In case of multiple R 906 are the same or different from each other, In R 907 In case of multiple, the multiple R 907 are the same or different from each other, In R 801 In case of multiple R 801 are the same or different from each other, In R 802 In case of plural, the plural R 802 are the same or different from each other.
23. The compound according to claim 22, wherein Ar1or Ar 10 is a group represented by the general formula (1100) or (1200).
24. The compound according to claim 22, wherein R other than a bond 111 ~R 120 R other than a bond 1201 ~R 1212 R other than a bond 1301 ~R 1314 R other than a bond 1401 ~R 1414 R other than a bond 1501 ~R 1514 R other than a bond 1601 ~R 1612 R other than a bond 1801 ~R 1812 each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, or a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms.
25. The compound according to claim 24, wherein R other than a bonding 111 ~R 120 , R other than a bonding 1201 ~R 1212 , R other than a bonding 1301 ~R 1314 , R other than a bonding 1401 ~R 1414 , R other than a bonding 1501 ~R 1514 , R other than a bonding 1601 ~R 1612 , and R other than a bonding 1801 ~R 1812 is a hydrogen atom.
26. The compound according to any one of claims 1 to 18, 20, and 23 to 25, wherein the group described as "substituted or unsubstituted" is a group that is "unsubstituted".
27. A compound which is the following compound BH1-1, BH1-2, BH1-4, BH1-5, BH1-6, BH1-7, BH1-8, BH1-9, BH1-10, BH1-11, BH1-12, BH1-13, BH1-14, BH1-22, BH1-23, BH1-24, BH1-25, BH1-26, BH1-27, BH1-28, BH1-29, or BH1-30, 。 28. An organic electroluminescent element comprising: an anode, a cathode, and an organic layer provided between the anode and the cathode, the organic layer includes a light-emitting layer, at least one of the organic layers includes the compound according to any one of claims 1 to 27.
29. The organic electroluminescent element according to claim 28, wherein the light-emitting layer includes the compound.
30. An organic electroluminescent element comprising: an anode, a cathode, and a light-emitting layer provided between the anode and the cathode, the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, the first light-emitting layer contains a first compound, the first compound is a compound represented by the following general formula (100) having at least one group represented by the following general formula (110), in the general formula (100), consisting of adjacent 2 or more selected from the group consisting of R 10 ~R 19 consisting of adjacent 2 or more selected from the group consisting of R R 10 ~R 19 each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aromatic group having 6 to 50 ring-forming carbon atoms, or the group represented by the general formula (110), wherein R 10 ~R 19 at least one of R is a group of the general formula (110), in the case where a plurality of groups represented by the general formula (110) are present, the plurality of groups represented by the general formula (110) are the same as or different from each other, L 100 To a single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, mx is 1, 2, or 3, In L 100 In case of 2 or more, the 2 or more L 100 are the same or different from each other, Ar 100 is an aryl group substituted or unsubstituted with 4 or more condensed benzene rings, Ar 100 does not comprise an anthracene ring, In Ar 100 In the case where there are two or more, the two or more Ar 100 are the same or different from each other, in the general formula (110) represents a bonding position, wherein the first compound does not include a cyano group in the molecule.
31. The organic electroluminescent element according to claim 30, wherein the first light-emitting layer is included between the anode and the cathode, The second light-emitting layer is included between the first light-emitting layer and the cathode.
32. The organic electroluminescent device according to claim 30, wherein The first light-emitting layer directly contacts the second light-emitting layer.
33. The organic electroluminescent device according to any one of claims 30 to 32, wherein The first compound is represented by General Formula (101) or General Formula (102) below, In General Formula (101) and General Formula (102), R 10 ~R 19 each independently R 10 ~R 19 have the same meaning, Ar 100 , L 100 and mx have the same meaning as Ar 100 , L 100 and mx in the general formula (110), respectively.
34. The organic electroluminescent device according to any one of claims 30 to 32, wherein R of the group represented by the general formula (110) 10 ~R 19 each independently is a hydrogen atom, a substituted or unsubstituted alkyl group with a carbon number of 1 to 20, a substituted or unsubstituted cycloalkyl group with a ring-constituting carbon number of 3 to 20, or a substituted or unsubstituted aryl group with a ring-constituting carbon number of 6 to 30.
35. The organic electroluminescent device according to claim 34, wherein R is not a group represented by the general formula (110) 10 ~R 19 is a hydrogen atom.
36. The organic electroluminescent device according to any one of claims 30 to 32, wherein The compound represented by General Formula (100) and having at least one group represented by General Formula (110) is represented by General Formula (123), General Formula (124), General Formula (125), or General Formula (126) below, In General Formula (123), General Formula (124), General Formula (125), and General Formula (126), X is an oxygen atom, L 10 To a substituted or unsubstituted arylene group with a ring-constituting carbon number of 6 to 15, Ar 10 an aryl group having 4 or more condensed benzene rings, Ar 11 is a substituted or unsubstituted aromatic group having 6 to 14 ring-forming carbon atoms, wherein Ar 11 other than substituted or unsubstituted anthracenyl, m10 is 5, m11 is 6, Rm is each independently a hydrogen atom, a substituted or unsubstituted alkyl group with a carbon number of 1 to 50, a substituted or unsubstituted cycloalkyl group with a ring-constituting carbon number of 3 to 50, or a substituted or unsubstituted aryl group with a ring-constituting carbon number of 6 to 50, a plurality of Rm are not bonded to each other.
37. The organic electroluminescent device according to claim 36, wherein The compound represented by General Formula (123) is represented by General Formula (1230) below, the compound represented by General Formula (124) is represented by General Formula (1240) below, the compound represented by General Formula (125) is represented by General Formula (1250) below, and the compound represented by General Formula (126) is represented by General Formula (1260) below, In General Formula (1230), General Formula (1240), General Formula (1250), and General Formula (1260), X, L 10 , Ar 10 , Ar 11 , m10, m11 and Rmare each independently of the meanings of X, L 10 , Ar 10 , Ar 11 , m10, m11 and Rmare each independently of the meanings of X, L 38. The organic electroluminescent device according to any one of claims 30 to 32, wherein Ar 100 an aryl group condensed with 4 benzene rings which may be substituted or unsubstituted, or an aryl group condensed with 5 benzene rings which may be substituted or unsubstituted.
39. The organic electroluminescent device according to any one of claims 30 to 32, wherein Ar 100 a group represented by the following general formula (1100), (1200), (1300), (1400), (1500), (1600) or (1800), In the general formula (1100), R 111 ~R 120 one of them is a bond, In the general formula (1200), R 1201 ~R 1212 one of them is a bond, In the general formula (1300), R 1301 ~R 1314 one of them is a bond, In the general formula (1400), R 1401 ~R 1414 one of them is a bond, In the general formula (1500), R 1501 ~R 1514 one of them is a bond, In the general formula (1600), R 1601 ~R 1612 one of them is a bond, In the general formula (1800), R 1801 ~R 1812 one of them is a bond, R other than a bond 111 ~R 120 , R other than a bond 1201 ~R 1212 , R other than a bond 1301 ~R 1314 , R other than a bond 1401 ~R 1414 , R other than a bond 1501 ~R 1514 , R other than a bond 1601 ~R 1612 , and R other than a bond 1801 ~R 1812 each independently is a hydrogen atom, a substituted or unsubstituted alkyl group with a carbon number of 1 to 50, a substituted or unsubstituted halogenated alkyl group with a carbon number of 1 to 50, a substituted or unsubstituted alkenyl group with a carbon number of 2 to 50, a substituted or unsubstituted alkynyl group with a carbon number of 2 to 50, a substituted or unsubstituted cycloalkyl group with a ring-constituting carbon number of 3 to 50, -Si(R 901 )(R 902 )(R 903 ) shown in the formula (1), -O-(R 904 ) a group represented by the formula: -S-(R 905 ) groups, -N(R 906 (R) 907 The groups shown in the figure, a substituted or unsubstituted aralkyl group with a carbon number of 7 to 50, -C(=O)R 801 groups shown, -COOR 802 groups shown, a halogen atom, a nitro group, a substituted or unsubstituted aryl group with a ring-constituting carbon number of 6 to 50, or a substituted or unsubstituted heterocyclic group with a ring-constituting atom number of 5 to 50, Here, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group with a carbon number of 1 to 50, a substituted or unsubstituted cycloalkyl group with a ring-constituting carbon number of 3 to 50, a substituted or unsubstituted aryl group having a ring-constituting carbon number of 6 to 50, or a substituted or unsubstituted heterocyclic group having a ring-constituting atom number of 5 to 50, In R 901 In case of multiple R 901 are the same or different from each other, In R 902 In case of multiple, the multiple R 902 are the same or different from each other, In R 903 In case of multiple, the multiple R 903 are the same or different from each other, In R 904 In case of multiple, the multiple R 904 are the same or different from each other, In R 905 In case of multiple, the multiple R 905 are the same or different from each other, in R 906 In case of a plurality, the plurality of R 906 are mutually identical or different, In R 907 In case of multiple, the multiple R 907 are the same or different from each other, In R 801 In case of multiple, the multiple R 801 are the same or different from each other, In R 802 In case of multiple, the multiple R 802 are the same or different from each other.
40. The organic electroluminescent device according to any one of claims 30 to 32, wherein the second light-emitting layer comprises a second compound represented by the following general formula (2), in the general formula (2), R 201 ~R 208 each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having a carbon number of 1 to 50, a substituted or unsubstituted haloalkyl group having a carbon number of 1 to 50, a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50, a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50, a substituted or unsubstituted cycloalkyl group having a ring-constituting carbon number of 3 to 50, -Si(R 901 )(R 902 )(R 903 ) shown in the formula (1), -O-(R 904 ) represents a group of the formula (R 904 ) represents a group of the formula (R -S-(R 905 ) groups, -N(R 906 )(R 907 ) represents a group of the formula: -N(R 906 )(R 907 ) represents a group of the formula: a substituted or unsubstituted aralkyl group having a carbon number of 7 to 50, -C(=O)R 801 groups shown, -COOR 802 groups shown, a halogen atom, a nitro group, a substituted or unsubstituted aryl group having a ring-constituting carbon number of 6 to 50, or a substituted or unsubstituted heterocyclic group having a ring-constituting atom number of 5 to 50, L 201 and L 202 each independently is a single bond, a substituted or unsubstituted arylene group having a ring-constituting carbon number of 6 to 50, or a substituted or unsubstituted divalent heterocyclic group having a ring-constituting atom number of 5 to 50, Ar 201 and Ar 202 each independently is a substituted or unsubstituted aryl group having a ring-constituting carbon number of 6 to 50, or a substituted or unsubstituted heterocyclic group having a ring-constituting atom number of 5 to 50, In the second compound represented by the general formula (2), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having a carbon number of 1 to 50, a substituted or unsubstituted cycloalkyl group having a ring-constituting carbon number of 3 to 50, a substituted or unsubstituted aryl group having a ring-constituting carbon number of 6 to 50, or a substituted or unsubstituted heterocyclic group having a ring-constituting atom number of 5 to 50, In R 901 In case of multiple, the multiple R 901 are the same or different from each other, In R 902 In case of multiple, the multiple R 902 are the same or different from each other, In R 903 In case of multiple, the multiple R 903 are the same or different from each other, In R 904 In case of multiple, the multiple R 904 are the same or different from each other, In R 905 In case of multiple, the multiple R 905 are the same or different from each other, In R 906 In case of multiple, the multiple R 906 are the same or different from each other, In R 907 In case of multiple, the multiple R 907 are the same or different from each other, In R 801 In case of multiple, the multiple R 801 are the same or different from each other, In R 802 In case of multiple, the multiple R 802 are the same or different from each other.
41. The organic electroluminescent device according to claim 40, wherein R 201 ~R 208 each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having a carbon number of 1 to 50, a substituted or unsubstituted haloalkyl group having a carbon number of 1 to 50, a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50, a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50, a substituted or unsubstituted cycloalkyl group having a ring-constituting carbon number of 3 to 50, -Si(R 901 )(R 902 )(R 903 ) shown in the formula (1), -O-(R 904 ) represents a group of the formula (R 904 ) represents a group of the formula (R -S-(R 905 ) represents a group of the formula (R 905 ) represents a group of the formula (R -N(R 906 (R) 907 The groups shown in the figure, a substituted or unsubstituted aralkyl group having a carbon number of 7 to 50, -C(=O)R 801 groups shown, -COOR 802 groups shown, a halogen atom, or a nitro group, L 201 and L 202 each independently is a single bond, a substituted or unsubstituted arylene group having a ring-constituting carbon number of 6 to 50, or a substituted or unsubstituted divalent heterocyclic group having a ring-constituting atom number of 5 to 50, Ar 201 and Ar 202 each independently is a substituted or unsubstituted aryl group having a ring-constituting carbon number of 6 to 50, or a substituted or unsubstituted heterocyclic group having a ring-constituting atom number of 5 to 50.
42. The organic electroluminescent device according to claim 40, wherein L 201 and L 202 each independently is a single bond, or a substituted or unsubstituted arylene group having a ring-constituting carbon number of 6 to 50, Ar 201 and Ar 202 each independently is a substituted or unsubstituted alicyclic group having a ring carbon number of 3 to 20.
43. The organic electroluminescent device according to claim 40, wherein Ar 201 and Ar 202 each independently is a phenyl group, a naphthyl group, a phenanthryl group, a biphenyl group, a terphenyl group, a diphenylfluorenyl group, a dimethylfluorenyl group, a benzo biphenylfluorenyl group, a benzo dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzoxanthlenyl group, a naphthobenzofuranyl group, or a naphthobenzothiophenyl group.
44. The organic electroluminescent device according to claim 40, wherein the second compound represented by the general formula (2) is a compound represented by the following general formula (201), general formula (202), general formula (203), general formula (204), general formula (205), general formula (206), general formula (207), general formula (208) or general formula (209), in the general formulae (201) to (209), a hydrogen atom, a substituted or unsubstituted alkyl group having a carbon number of 1 to 50, a substituted or unsubstituted haloalkyl group having a carbon number of 1 to 50, a substituted or unsubstituted alkenyl group having a carbon number of 2 to 50, a substituted or unsubstituted alkynyl group having a carbon number of 2 to 50, a substituted or unsubstituted cycloalkyl group having a ring-constituting carbon number of 3 to 50, a substituted or unsubstituted aralkyl group having a carbon number of 7 to 50, a halogen atom, a nitro group, a single bond, a substituted or unsubstituted arylene group having a ring-constituting carbon number of 6 to 50, or a substituted or unsubstituted divalent heterocyclic group having a ring-constituting atom number of 5 to 50, a substituted or unsubstituted aryl group having a ring-constituting carbon number of 6 to 50, or a substituted or unsubstituted heterocyclic group having a ring-constituting atom number of 5 to 50. L 201 and Ar 201 have the same meaning as L 201 and Ar 201 in the general formula (2), R 201 ~R 208 each independently of the other R 201 ~R 208 have the same meaning.
45. The organic electroluminescent device according to any one of claims 30 to 32, wherein a hole-transporting layer is provided between the anode and the light-emitting layer.
46. The organic electroluminescent device according to any one of claims 30 to 32, wherein an electron-transporting layer is provided between the cathode and the light-emitting layer.
47. The organic electroluminescent device according to any one of claims 30 to 32, wherein the first light-emitting layer further contains a third compound having a fluorescent light-emitting property, the third compound is a compound that shows light emission with a peak wavelength of 430 nm or more and 480 nm or less.
48. The organic electroluminescent device according to claim 47, wherein the first compound is a first host material.
49. The organic electroluminescent device according to claim 48, wherein the first light-emitting layer contains the first compound as the first host material and the third compound as the first dopant material.
50. The organic electroluminescent device according to claim 49, wherein a relationship of the following mathematical formula (Mathematical Formula 1) is satisfied between a singlet energy S1(H1) of the first compound and a singlet energy S1(D3) of the third compound, S1(H1) > S1(D3)... (Mathematical Formula 1).
51. The organic electroluminescent device according to any one of claims 30 to 32, wherein the second light-emitting layer further contains a fourth compound having a fluorescent light-emitting property, the fourth compound is a compound that shows light emission with a peak wavelength of 430 nm or more and 480 nm or less.
52. The organic electroluminescent device according to claim 51, wherein the second compound is a second host material.
53. The organic electroluminescent device according to claim 52, wherein the second light-emitting layer contains the second compound as the second host material and the fourth compound as the second dopant material.
54. The organic electroluminescent device according to claim 53, wherein a relationship of the following mathematical formula (Mathematical Formula 2) is satisfied between a singlet energy S1(H2) of the second compound and a singlet energy S1(D4) of the fourth compound, S1(H2) > S1(D4)... (Mathematical Formula 2).
55. The organic electroluminescent device according to any one of claims 30 to 32, wherein the light-emitting layer does not contain a metal complex.
56. The organic electroluminescent device according to any one of claims 30 to 32, wherein the light-emitting layer does not contain a phosphorescent light-emitting material.
57. The organic electroluminescent device according to any one of claims 30 to 32, wherein the light-emitting layer does not contain a heavy metal complex and a phosphorescent light-emitting rare earth metal complex.
58. The organic electroluminescent device according to any one of claims 30 to 32, wherein in the first compound and the second compound, the groups described as "substituted or unsubstituted" are all groups that are "unsubstituted".
59. The organic electroluminescent device according to claim 30, wherein the first compound is compound BH1-1, BH1-2, BH1-4, BH1-5, BH1-6, BH1-7, BH1-8, BH1-9, BH1-10, BH1-11, BH1-12, BH1-13, BH1-14, BH1-22, BH1-23, BH1-24, BH1-25, BH1-26, or BH1-27, 。 60. The organic electroluminescent device according to any one of claims 28 to 32, which emits light having a main peak peak wavelength of 430 nm or more and 480 nm or less at the time of driving of the element.
61. An electronic device provided with the organic electroluminescent device according to any one of claims 28 to 60.
Citation Information
Patent Citations
Compound and organic light-emitting device including the same
US20150001479A1
Condensed cyclic compound and organic light-emitting device including the same
US20150069344A1
Condensed cyclic compound and organic light-emitting device comprising the same
US20150270498A1
Compound and organic light-emitting device including the same
US20170331051A1
Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN102933530A