Compounds, organic electroluminescent elements, and electronic devices
A benz[de]anthracene derivative compound enhances the performance of organic electroluminescent elements by improving luminous efficiency and lifespan, especially in stacked light-emitting layers.
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- IDEMITSU KOSAN CO LTD
- Filing Date
- 2026-02-04
- Publication Date
- 2026-06-02
AI Technical Summary
Existing organic electroluminescent elements face challenges in achieving a balance between luminous efficiency and lifespan, particularly in stacked light-emitting layers on the anode side.
A compound with a benz[de]anthracene derivative skeleton, represented by specific general formulas, is introduced into the light-emitting layer to enhance performance.
The compound improves the balance between luminous efficiency and lifespan of organic electroluminescent elements, particularly in multi-layer configurations.
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Figure 2026090349000631 
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Abstract
Description
[Technical Field]
[0001] This invention relates to compounds, organic electroluminescent elements, and electronic devices. [Background technology]
[0002] Organic electroluminescent elements (hereinafter sometimes referred to as "organic EL elements") are used in full-color displays for mobile phones and televisions. When a voltage is applied to an organic EL element, holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. At this time, according to the statistical laws of electron spin, singlet excitons are generated at a rate of 25%, and triplet excitons are generated at a rate of 75%. Various studies have been conducted on compounds used in organic EL elements to improve their performance (see, for example, Patent Documents 1 to 4). Examples of organic EL element performance include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan. [Prior art documents] [Patent Documents]
[0003] [Patent Document 1] U.S. Patent Application Publication No. 2015 / 270498 [Patent Document 2] U.S. Patent Application Publication No. 2015 / 001479 [Patent Document 3] U.S. Patent Application Publication No. 2015 / 069344 [Patent Document 4] U.S. Patent Application Publication No. 2017 / 331051 [Overview of the project] [Problems that the invention aims to solve]
[0004] One object of the present invention is to provide a compound capable of improving the performance of an organic EL element, an organic electroluminescence element containing the compound, and an electronic device equipped with the organic electroluminescence element. Another object of the present invention is to provide a compound that can be expected to provide an element with a good balance between luminous efficiency and lifespan when used in the light-emitting layer on the anode side of an organic electroluminescence element in which a plurality of light-emitting layers are stacked, an organic electroluminescence element containing the compound in the light-emitting layer on the anode side among the plurality of light-emitting layers, and an electronic device equipped with the organic electroluminescence element.
Means for Solving the Problems
[0005] According to one aspect of the present invention, there is provided 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.
[0006]
Chemical formula
[0007] (In the general formula (1000), X is an oxygen atom, a sulfur atom, C(R 2001 )(R 2002 ), or Si(R 2003 )(R 2004 ), R 2001 ~R 2004 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 10 ~R 19 Of these, one or more pairs consisting of two or more adjacent items, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 10 ~R 19 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Nitro group, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, or The group is represented by the general formula (11) above, However, R 10 ~R 19 At least one of them is a group represented by the general formula (11), If there are multiple groups represented by the general formula (11), the multiple groups represented by the general formula (11) may be identical or different from each other. L1 is A substituted or unsubstituted ring-forming arylene group with 6 to 15 carbon atoms, or A divalent heterocyclic group having 5 to 15 substituted or unsubstituted ring-forming atoms, mx is 1, 2, or 3. If there are two or more L1s, then the two or more L1s are either identical or different from each other. Ar1 is a substituted or unsubstituted aryl group containing four or more rings. If there are two or more Ar1s, then the two or more Ar1s are either identical or different from each other. In the general formula (11) above, * indicates the bond position, In the compound represented by the general formula (1000), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another. R 801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 They are either identical or different to one another.
[0008] According to one aspect of the present invention, a compound is provided that has at least one group represented by the following general formula (110A) and contains only one benz[de]anthracene derivative skeleton represented by the following general formula (1000A) in its molecule.
[0009] [ka]
[0010] (In the above general formula (1000A), X consists of an oxygen atom, a sulfur atom, and C(R). 2001 )(R 2002 ), or Si(R 2003 )(R 2004 ) and R 2001 ~R 2004 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 10 ~R 19 Of these, one or more pairs consisting of two or more adjacent items, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 10 ~R 19 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Nitro group, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, or The group is represented by the general formula (110A) mentioned above, However, R 13 and R 18 At least one of these is a group represented by the general formula (110A), If there are multiple groups represented by the general formula (110A), the multiple groups represented by the general formula (110A) may be identical or different from each other. L 100 teeth, single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, mx is 1, 2, or 3. L 100 If there are 2 or more, then 2 or more L 100are the same as or different from each other, Ar1 is a substituted or unsubstituted aryl group containing four or more rings, When two or more Ar1 are present, the two or more Ar1 are the same as or different from each other, * in the general formula (110A) indicates the bonding position, In the compound represented by the 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, 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 aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 901 When a plurality of R 901 are present, the plurality of R R 902 When a plurality of R 902 are present, the plurality of R R 903 When a plurality of R 903 are present, the plurality of R R 904 When a plurality of R 904 are present, the plurality of R R 905 When a plurality of R 905 are present, the plurality of R R 906 When a plurality of R 906 are present, the plurality of R R 907 When a plurality of R 907They are either identical or different from one another. R 801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 They are either identical or different to one another.
[0011] According to one aspect of the present invention, an organic electroluminescent element is provided, having an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes a light-emitting layer, and at least one layer of the organic layer contains a compound according to one aspect of the present invention.
[0012] According to one aspect of the present invention, an organic electroluminescent element is provided, comprising an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, wherein 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 having at least one group represented by the following general formula (110) and being a compound represented by the following general formula (1000B).
[0013] [ka]
[0014] (In the above general formula (1000B), X consists of an oxygen atom, a sulfur atom, and C(R). 2001 )(R 2002 ), or Si(R 2003 )(R 2004 ) and R 2001 ~R 2004 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 10 ~R 19 Of these, one or more pairs consisting of two or more adjacent items, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 10 ~R 19 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Nitro group, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, or The group is represented by the general formula (110) above, However, R 10 ~R 19 At least one of them is a group represented by the general formula (110), If there are multiple groups represented by the general formula (110), the multiple groups represented by the general formula (110) may be identical or different from each other. L 100 teeth, single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, mx is 1, 2, or 3. L 100 If there are 2 or more, then 2 or more L 100 They are either identical or different from each other. Ar 100 teeth, A substituted or unsubstituted aryl group containing three or more rings, or A substituted or unsubstituted heterocyclic group comprising two or more aromatic rings and one or more heterocyclic rings, Ar 100 It does not contain an anthracene ring, Ar 100 If there are 2 or more Ar 100 They are either identical or different from each other. In the above general formula (110), * indicates the bond position, In the first compound represented by the general formula (1000B), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another. R 801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 They are either identical or different to one another.
[0015] According to one aspect of the present invention, an electronic device equipped with an organic electroluminescent element according to one aspect of the present invention is provided. [Effects of the Invention]
[0016] According to one aspect of the present invention, a compound that can improve the performance of an organic EL element, an organic electroluminescent element containing the compound, and an electronic device equipped with the organic electroluminescent element can be provided. Furthermore, according to one aspect of the present invention, when used in the anode-side light-emitting layer of an organic electroluminescent element having multiple light-emitting layers stacked together, it is possible to provide a compound that can be expected to provide an element with a good balance between luminous efficiency and lifespan, an organic electroluminescent element that includes the compound in the anode-side light-emitting layer among the multiple light-emitting layers, and an electronic device equipped with the organic electroluminescent element. [Brief explanation of the drawing]
[0017] [Figure 1] This figure shows a schematic configuration of an example of an organic electroluminescent element according to one embodiment of the present invention. [Modes for carrying out the invention]
[0018] [Definition] In this specification, the term "hydrogen atom" includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.
[0019] In this specification, in chemical structural formulas, any bondable positions where symbols such as "R" or "D" representing a deuterium atom are not explicitly indicated shall be assumed to be bonded to hydrogen atoms, i.e., light hydrogen atoms, deuterium atoms, or tritium atoms.
[0020] In this specification, the ring-forming carbon number refers to the number of carbon atoms among the atoms constituting the ring itself in a compound with a structure in which atoms are bonded in a ring (e.g., monocyclic compounds, fused ring compounds, crosslinked compounds, carbocyclic compounds, and heterocyclic compounds). If the ring is substituted by a substituent, the carbon atoms in the substituent are not included in the ring-forming carbon number. The same applies to the "ring-forming carbon number" described below unless otherwise specified. For example, a benzene ring has 6 ring-forming carbon atoms, a naphthalene ring has 10 ring-forming carbon atoms, a pyridine ring has 5 ring-forming carbon atoms, and a furan ring has 4 ring-forming carbon atoms. Also, for example, the ring-forming carbon number of a 9,9-diphenylfluorenyl group is 13, and the ring-forming carbon number of a 9,9'-spirobifluorenyl group is 25. Furthermore, when a benzene ring is substituted with an alkyl group, for example, the number of carbon atoms in that alkyl group is not included in the number of ring-forming carbon atoms of the benzene ring. Therefore, the number of ring-forming carbon atoms in a benzene ring substituted with an alkyl group is 6. Similarly, when a naphthalene ring is substituted with an alkyl group, for example, the number of carbon atoms in that alkyl group is not included in the number of ring-forming carbon atoms of the naphthalene ring. Therefore, the number of ring-forming carbon atoms in a naphthalene ring substituted with an alkyl group is 10.
[0021] In this specification, the number of ring-forming atoms refers to the number of atoms that constitute the ring itself in compounds with a ring-bonded structure (e.g., monocyclic compounds, fused rings, and ring aggregates) (e.g., monocyclic compounds, fused ring compounds, bridged compounds, carbocyclic compounds, and heterocyclic compounds). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the bonds of ring-forming atoms) and atoms included in substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. The same applies to "number of ring-forming atoms" as described below unless otherwise specified. For example, the number of ring-forming atoms in a pyridine ring is 6, the number of ring-forming atoms in a quinazoline ring is 10, and the number of ring-forming atoms in a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring, or the number of atoms constituting substituents, are not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms in a pyridine ring to which hydrogen atoms or substituents are bonded is 6. Furthermore, for example, hydrogen atoms bonded to the carbon atom of the quinazoline ring, or atoms constituting substituents, are not included in the number of ring-forming atoms of the quinazoline ring. Therefore, the number of ring-forming atoms of a quinazoline ring to which hydrogen atoms or substituents are bonded is 10.
[0022] In this specification, the expression "substituted or unsubstituted ZZ group having XX to YY carbon atoms" means that "XX to YY carbon atoms" represents the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of substituents when it is substituted. Here, "YY" is greater than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.
[0023] In this specification, the expression "ZZ group with substituted or unsubstituted atoms of XX to YY" means that "atom count XX to YY" represents the number of atoms when the ZZ group is unsubstituted, and does not include the number of substituent atoms when it is substituted. Here, "YY" is greater than "XX", where "XX" is an integer of 1 or more, and "YY" is an integer of 2 or more.
[0024] In this specification, an unsubstituted ZZ group refers to a case where "substituted or unsubstituted ZZ group" is "unsubstituted ZZ group," and a substituted ZZ group refers to a case where "substituted or unsubstituted ZZ group" is "substituted ZZ group." In this specification, "unsubstituted" in the context of a "substituted or unsubstituted ZZ group" means that the hydrogen atoms in the ZZ group are not replaced by substituents. The hydrogen atoms in an "unsubstituted ZZ group" are light hydrogen atoms, deuterium atoms, or tritium atoms. Furthermore, in this specification, "substituted" in the context of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. Similarly, "substituted" in the context of "BB group substituted with AA group" means that one or more hydrogen atoms in the BB group are replaced by an AA group.
[0025] "Substituents as described herein" The substituents described herein will be explained below.
[0026] The number of ring-forming carbon atoms in the "unsubstituted aryl group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein. The number of ring-forming atoms in the "unsubstituted heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkyl group" as described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkenyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkynyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of ring-forming carbon atoms in the "unsubstituted cycloalkyl groups" described herein is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified herein. The number of ring-forming carbon atoms in the "unsubstituted arylene group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein. The number of ring-forming atoms in the "unsubstituted divalent heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkylene group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein.
[0027] • "substituted or unsubstituted aryl groups" Specific examples of "substituted or unsubstituted aryl groups" as described herein (Specific Examples Group G1) include the following unsubstituted aryl groups (Specific Examples Group G1A) and substituted aryl groups (Specific Examples Group G1B), etc. (Here, "unsubstituted aryl group" refers to the case where "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and "substituted aryl group" refers to the case where "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, the term "aryl group" simply includes both "unsubstituted aryl groups" and "substituted aryl groups." A "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced by substituents. Examples of "substituted aryl groups" include the groups in which one or more hydrogen atoms of an "unsubstituted aryl group" in specific example group G1A below are replaced by substituents, and the examples of substituted aryl groups in specific example group G1B below. Note that the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed here are merely examples, and the "substituted aryl groups" described herein also include groups in which the hydrogen atoms bonded to the carbon atom of the aryl group itself in the "substituted aryl group" in specific example group G1B below are further replaced by substituents, and groups in which the hydrogen atoms of the substituent in the "substituted aryl group" in specific example group G1B below are further replaced by substituents.
[0028] • Unsubstituted aryl groups (specific examples group G1A): Phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-Naphthyl group, 2-Naphthyl group, anthryl group, Benzoantryl group, Phenanthryl group, Benzophenanthryl group, Phenalenyl group, Pyrenyl group, Chrysenyl group, Benzocrisenyl group, Triphenylenyl group, Benzotriphenylenyl group, Tetraceryl group, Pentacenyl group, Fluorenyl group, 9,9'-Spirobifluorenyl group, Benzofluorenyl group, Dibenzofluorenyl group, Fluoranthenyl group, Benzofluoranthenyl group, Perilenyl group, and A monovalent aryl group derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).
[0029] [ka]
[0030] [ka]
[0031] • Substitutive aryl groups (Specific examples group G1B): o-Tryl group, m-tolyl group, p-tril group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, Meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, Cyanophenyl group, Triphenylsilylphenyl group, Trimethylsilylphenyl group, Phenylnaphthyl group, Naphthylphenyl group, and A group obtained by replacing one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the general formulas (TEMP-1) to (TEMP-15) above with substituents.
[0032] • "Substitutable or unsubstituted heterocyclic groups" The “heterocyclic group” as described herein is a cyclic group containing at least one heteroatom in its ring-forming atoms. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron. The "heterocyclic group" as described herein is either a monocyclic group or a fused-cyclic group. The term "heterocyclic group" as used herein refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples of "substituted or unsubstituted heterocyclic groups" as described herein (Specific Examples Group G2) include the following unsubstituted heterocyclic groups (Specific Examples Group G2A) and substituted heterocyclic groups (Specific Examples Group G2B), etc. (Here, "unsubstituted heterocyclic group" refers to the case where "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group," and "substituted heterocyclic group" refers to the case where "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group.") In this specification, the term "heterocyclic group" simply includes both "unsubstituted heterocyclic groups" and "substituted heterocyclic groups." A "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by substituents. Specific examples of "substituted heterocyclic groups" include the groups in specific example group G2A below in which hydrogen atoms of an "unsubstituted heterocyclic group" are replaced, and the examples of substituted heterocyclic groups in specific example group G2B below. Note that the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are merely examples, and the "substituted heterocyclic groups" described herein also include groups in which hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself are further replaced by substituents, and groups in which hydrogen atoms of substituents are further replaced by substituents.
[0033] The specific examples 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 structure represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).
[0034] Specific examples group G2B includes, for example, substituted heterocyclic groups containing a nitrogen atom (Specific Examples Group G2B1), substituted heterocyclic groups containing an oxygen atom (Specific Examples Group G2B2), substituted heterocyclic groups containing a sulfur atom (Specific Examples Group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (Specific Examples Group G2B4).
[0035] • Unsubstituted heterocyclic groups containing a nitrogen atom (specific examples group G2A1): Pyrrolyl group, imidazolyl group, Pyrazolyl group, Triazolyl group, Tetrazolyl group, Oxazolyl group, isoxazolyl group, Oxadiazolyl group, Thiazolyl group, isothiazolyl group, Thiadianzolyl group, Pyridyl group, Pyridazinyl group, Pyrimidinyl group, pyrazinyl group, Triazinyl group, Indolyl group, isoindolyl group, indolidinyl group, Quinolidinyl group, quinolyl group, Isoquinolyl group, cinnolyl group, Phthalazinyl group, Quinazolinyl group, Quinoxalinyl group, Benzimidazolyl group, Indazolyl group, Phenanthrolinyl group, Phenantridinyl group, Acridinyl group, Phenazinyl group, Carbazolyl group, Benzocarbazolyl group, Morpholino group, Phenoxadinyl group, Phenothiazinyl group, azacarbazolyl group, and Diazacarbazolyl group.
[0036] • Unsubstituted heterocyclic groups containing an oxygen atom (specific examples group G2A2): Frill group, Oxazolyl group, isoxazolyl group, Oxadiazolyl group, xanthenyl group, Benzofuranyl group, Isobenzofuranyl group, Dibenzofuranyl group, Naphthobenzofuranyl group, Benzoxazolyl group, Benzoisoxazolyl group, Phenoxadinyl group, Morpholino group, Dinaphthofuranyl group, Azadibenzofuranyl group, Diazadibenzofuranyl group, Azanaftobenzofuranyl group, and Diazanaphthobenzofuranyl group.
[0037] • Unsubstituted heterocyclic groups containing a sulfur atom (specific examples group G2A3): Thienyl group, Thiazolyl group, isothiazolyl group, Thiadianzolyl group, Benzothiophenyl group (benzothienyl group), Isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), Naphthobenzothiophenyl group (naphthobenzothienyl group), Benzothiazolyl group, Benzoisothiazolyl group, Phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), azadibenzothiophenyl group (azadibenzothienyl group), Diazadibenzothiophenyl group (diazadibenzothienyl group), Azanaphtobenzothiophenyl group (azanaphthobenzothienyl group), and Diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).
[0038] • Monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (Specific examples group G2A4):
[0039] [ka]
[0040] [ka]
[0041] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each of these is independently an oxygen atom, a sulfur atom, NH, or CH2. However, X A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH. In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A If at least one of the members is NH or CH2, the monovalent heterocyclic groups derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) include monovalent groups obtained by removing one hydrogen atom from these NH or CH2 members.
[0042] • Heterocyclic groups with substitutions containing a nitrogen atom (Specific examples group G2B1): (9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, Diphenylcarbazole-9-yl group, Phenylcarbazole-9-yl group, Methyl benzimidazolyl group, Ethyl benzimidazolyl group, Phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, Phenylquinazolinyl group, and Biphenylylquinazolinyl group.
[0043] • Heterocyclic groups with substitutions containing an oxygen atom (Specific examples group G2B2): Phenyldibenzofuranyl group, Methyldibenzofuranyl group, t-butyldibenzofuranyl group, and A monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].
[0044] • Heterocyclic groups with substitutions containing a sulfur atom (specific examples group G2B3): Phenyldibenzothiophenyl group, Methyldibenzothiophenyl group, t-butyldibenzothiophenyl group, and A monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].
[0045] • Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (specific examples group G2B4):
[0046] The aforementioned "one or more hydrogen atoms of a monovalent heterocyclic group" refers to hydrogen atoms bonded to the ring-forming carbon atoms of the monovalent heterocyclic group, X A and Y A A hydrogen atom bonded to a nitrogen atom when at least one of them is NH, and X A and Y AThis refers to one or more hydrogen atoms selected from the hydrogen atoms of the methylene group when one of the atoms is CH2.
[0047] • "Substituted or unsubstituted alkyl groups" Specific examples of "substituted or unsubstituted alkyl groups" as described herein (Specific Examples Group G3) include the following unsubstituted alkyl groups (Specific Examples Group G3A) and substituted alkyl groups (Specific Examples Group G3B). (Here, "unsubstituted alkyl group" refers to the case where "substituted or unsubstituted alkyl group" is "unsubstituted alkyl group," and "substituted alkyl group" refers to the case where "substituted or unsubstituted alkyl group" is "substituted alkyl group.") Hereafter, "alkyl group" simply refers to both "unsubstituted alkyl groups" and "substituted alkyl groups." A "substituted alkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are replaced by substituents. Specific examples of "substituted alkyl groups" include the groups in which one or more hydrogen atoms in the "unsubstituted alkyl groups" (specific example group G3A) below are replaced by substituents, and examples of substituted alkyl groups (specific example group G3B). In this specification, the alkyl group in "unsubstituted alkyl group" refers to a linear alkyl group. Therefore, "unsubstituted alkyl groups" include both linear "unsubstituted alkyl groups" and branched "unsubstituted alkyl groups". The examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed here are merely examples, and the "substituted alkyl groups" described herein also include groups in which the hydrogen atoms of the alkyl group itself in the "substituted alkyl groups" of specific example group G3B are further replaced by substituents, and groups in which the hydrogen atoms of the substituent in the "substituted alkyl groups" of specific example group G3B are further replaced by substituents.
[0048] • Unsubstituted alkyl groups (specific examples group G3A): Methyl group, Ethyl group, n-propyl group, Isopropyl group, n-butyl group, isobutyl group, s-butyl group, and t-butyl group.
[0049] • Substituting alkyl groups (specific examples group G3B): Heptafluoropropyl group (including isomers), Pentafluoroethyl group, 2,2,2-trifluoroethyl group, and Trifluoromethyl group.
[0050] • "Substituted or unsubstituted alkenyl groups" Specific examples of "substituted or unsubstituted alkenyl groups" as described herein (Specific Examples Group G4) include the following unsubstituted alkenyl groups (Specific Examples Group G4A) and substituted alkenyl groups (Specific Examples Group G4B), etc. (Here, "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and "substituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply includes both "unsubstituted alkenyl groups" and "substituted alkenyl groups." A "substituted alkenyl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted alkenyl group" are replaced by substituents. Specific examples of "substituted alkenyl groups" include groups in which the "unsubstituted alkenyl group" (Specific Example Group G4A) has substituents, and examples of substituted alkenyl groups (Specific Example Group G4B). Note that the examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed here are merely examples, and the "substituted alkenyl groups" described herein also include groups in which the hydrogen atoms of the alkenyl group itself in the "substituted alkenyl group" of Specific Example Group G4B are further replaced by substituents, and groups in which the hydrogen atoms of the substituent in the "substituted alkenyl group" of Specific Example Group G4B are further replaced by substituents.
[0051] • Unsubstituted alkenyl groups (specific examples group G4A): vinyl group, allyl group, 1-Butenyl group, 2-butenyl group, and 3-Butenyl group.
[0052] • Substitutive alkenyl groups (specific examples group G4B): 1,3-butanedienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-dimethylallyl group.
[0053] • "Substituted or unsubstituted alkynyl groups" Specific examples of "substituted or unsubstituted alkynyl groups" as described herein (Specific Examples Group G5) include the following unsubstituted alkynyl groups (Specific Examples Group G5A), etc. (Here, "unsubstituted alkynyl group" refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group.") Hereafter, when simply referred to as "alkynyl group," it includes both "unsubstituted alkynyl groups" and "substituted alkynyl groups." A "substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced by substituents. Specific examples of "substituted alkynyl groups" include groups in which one or more hydrogen atoms in an "unsubstituted alkynyl group" (specific example group G5A) are replaced by substituents.
[0054] • Unsubstituted alkynyl groups (specific examples group G5A): Ethynyl group.
[0055] • "Substituted or unsubstituted cycloalkyl groups" Specific examples of "substituted or unsubstituted cycloalkyl groups" as described herein (Specific Examples Group G6) include the following unsubstituted cycloalkyl groups (Specific Examples Group G6A) and substituted cycloalkyl groups (Specific Examples Group G6B), etc. (Here, "unsubstituted cycloalkyl group" refers to the case where "substituted or unsubstituted cycloalkyl group" is "unsubstituted cycloalkyl group," and "substituted cycloalkyl group" refers to the case where "substituted or unsubstituted cycloalkyl group" is "substituted cycloalkyl group.") In this specification, the term "cycloalkyl group" simply includes both "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups." A "substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are replaced by a substituent. Specific examples of "substituted cycloalkyl groups" include the groups in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" (specific example group G6A) are replaced by a substituent, and examples of substituted cycloalkyl groups (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed here are merely examples, and the "substituted cycloalkyl groups" described herein also include groups in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself are replaced by a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted cycloalkyl group" of specific example group G6B are further replaced by a substituent.
[0056] • Unsubstituted cycloalkyl groups (specific examples group G6A): Cyclopropyl group, Cyclobutyl group, Cyclopentyl group, Cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.
[0057] • Substituting cycloalkyl groups (specific examples group G6B): 4-methylcyclohexyl group.
[0058] · "-Si(R 901 )(R 902 )(R 903 ) represented by the base -Si(R 901 )(R 902 )(R 903 ) Examples of the base represented by (Example Group G7) are: -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6) Here are some examples. G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6. In -Si(G1)(G1)(G1), the multiple G1s are either identical or different from one another. In -Si(G1)(G2)(G2), the multiple G2s are either identical or different from one another. In -Si(G1)(G1)(G2), the multiple G1s are either identical or different from one another. In -Si(G2)(G2)(G2), the multiple G2s are either identical or different from one another. In -Si(G3)(G3)(G3), the multiple G3s are either identical or different from one another. In -Si(G6)(G6)(G6), the multiple G6s are either identical or different from one another.
[0059] ·「-O-(R 904 ) represented by the base The following information pertains to the -O-(R904 ) Examples of the base represented by (Example Group G8) are: -O(G1), -O(G2), -O(G3), and -O(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6.
[0060] · "-S-(R 905 ) represented by the base The following information pertains to the -S-(R 905 ) Examples of the base represented by (example group G9) are: -S(G1), -S(G2), -S(G3), and -S(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6.
[0061] · "-N(R 906 )(R 907 ) represented by the base -N(R) as described in this specification 906 )(R 907 ) Examples of the base represented by (Example Group G10) are: -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), Examples include -N(G3)(G3) and -N(G6)(G6). Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6. In -N(G1)(G1), multiple G1s are either identical or different from one another. In -N(G2)(G2), multiple G2s are either identical or different from one another. In -N(G3)(G3), multiple G3s are either identical or different from one another. In -N(G6)(G6), multiple G6s are either identical or different from one another.
[0062] • "Halogen atom" Specific examples of "halogen atoms" as described herein (Specific Examples Group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.
[0063] • "Substituted or unsubstituted fluoroalkyl groups" The terms "substituted or unsubstituted fluoroalkyl groups" as used herein refer to groups in which at least one hydrogen atom bonded to the carbon atoms constituting the alkyl group is replaced by a fluorine atom, and also include groups in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group are replaced by fluorine atoms (perfluoro groups). The number of carbon atoms in an "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. A "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced by substituents. The terms "substituted fluoroalkyl groups" as used herein also include groups in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain are further replaced by substituents, and groups in which one or more hydrogen atoms of a substituent are further replaced by substituents. Specific examples of "unsubstituted fluoroalkyl groups" include the example of a group in which one or more hydrogen atoms in the aforementioned "alkyl group" (specific example group G3) are replaced by fluorine atoms.
[0064] • "Substituted or unsubstituted haloalkyl groups" The terms "substituted or unsubstituted haloalkyl groups" as used herein refer to groups in which at least one hydrogen atom bonded to the carbon atoms constituting the alkyl group is replaced by a halogen atom, and also include groups in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group are replaced by halogen atoms. The number of carbon atoms in an "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. A "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of a "haloalkyl group" are replaced by substituents. The terms "substituted haloalkyl groups" as used herein also include groups in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain are further replaced by substituents, and groups in which one or more hydrogen atoms of a substituent are further replaced by substituents. Specific examples of "unsubstituted haloalkyl groups" include groups in which one or more hydrogen atoms of the aforementioned "alkyl group" (specific example group G3) are replaced by halogen atoms. Haloalkyl groups are sometimes referred to as alkyl halogens.
[0065] • "Substituted or unsubstituted alkoxy groups" A specific example of a "substituted or unsubstituted alkoxy group" as described herein is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. The number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein.
[0066] • "substituted or unsubstituted alkylthio groups" A specific example of the "substituted or unsubstituted alkylthio group" described herein is the group represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. The number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein.
[0067] • "Substituted or unsubstituted aryloxy groups" A specific example of a "substituted or unsubstituted aryloxy group" as described herein is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. The number of ring-forming carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein.
[0068] • "Substituted or unsubstituted arylthio groups" A specific example of the "substituted or unsubstituted arylthio group" described herein is the group represented by -S(G1), where G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring-forming carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein.
[0069] • "Substituted or unsubstituted trialkylsilyl groups" A specific example of the "trialkylsilyl group" described herein is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) are either identical or different from one another. Unless otherwise specified herein, the number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.
[0070] • "Substituted or unsubstituted aralkyl groups" Specific examples of the "substituted or unsubstituted aralkyl group" described herein include the group represented by -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3, and G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. Therefore, an "aralkyl group" is a group in which the hydrogen atom of an "alkyl group" is replaced by an "aryl group" as a substituent, and is one form of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" in which an "unsubstituted aryl group" is substituted, and the number of carbon atoms in the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified herein. Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.
[0071] Unless otherwise specified herein, the substituted or unsubstituted aryl groups are preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, pyrenyl, chrysenyl, triphenylenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl.
[0072] Unless otherwise specified herein, the substituted or unsubstituted heterocyclic groups are preferably pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, benzimidazolyl, phenanthrolinyl, carbazolyl (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, or 9-carbazolyl), benzocarbazolyl, azacarbazolyl, diazacarbazolyl, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophenyl, naphthobenzothiophenyl, aza These include dibenzothiophenyl group, diazadibenzothiophenyl group, (9-phenyl)carbazolyl group ((9-phenyl)carbazole-1-yl group, (9-phenyl)carbazole-2-yl group, (9-phenyl)carbazole-3-yl group, or (9-phenyl)carbazole-4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazole-9-yl group, phenylcarbazole-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group, etc.
[0073] In this specification, unless otherwise specified, the carbazolyl group is specifically one of the following groups:
[0074] [ka]
[0075] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically one of the following groups:
[0076] [ka]
[0077] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bond position.
[0078] In this specification, unless otherwise specified, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups:
[0079] [ka]
[0080] In the general formulas (TEMP-34) to (TEMP-41) above, * represents a bond position.
[0081] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and t-butyl groups.
[0082] • "Substituted or unsubstituted arylene group" Unless otherwise specified, the "substituted or unsubstituted arylene group" described herein is a divalent group derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described above. Specific examples of the "substituted or unsubstituted arylene group" (Specific Examples Group G12) include the divalent group derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described in Specific Examples Group G1.
[0083] • "Substitutable or unsubstituted divalent heterocyclic groups" Unless otherwise specified, the “substituted or unsubstituted divalent heterocyclic groups” described herein refer to divalent groups derived by removing one hydrogen atom from the heterocycle of the “substituted or unsubstituted heterocyclic groups” described above. Specific examples of “substituted or unsubstituted divalent heterocyclic groups” (Specific Examples Group G13) include the divalent groups derived by removing one hydrogen atom from the heterocycle of the “substituted or unsubstituted heterocyclic groups” described in Specific Examples Group G2.
[0084] • "Substituted or unsubstituted alkylene groups" Unless otherwise specified, the "substituted or unsubstituted alkylene groups" described herein are divalent groups derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl groups" described above. Specific examples of "substituted or unsubstituted alkylene groups" (Specific Examples Group G14) include the divalent groups derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl groups" described in Specific Examples Group G3.
[0085] Unless otherwise specified herein, the substituted or unsubstituted arylene groups are preferably any of the following general formulas (TEMP-42) to (TEMP-68).
[0086] [ka]
[0087] [ka]
[0088] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each of these is independently either a hydrogen atom or a substituent. In the general formulas (TEMP-42) to (TEMP-52) above, * represents a bond position.
[0089] [ka]
[0090] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each of these is independently either a hydrogen atom or a substituent. Equations Q9 and Q 10 These elements may be bonded to each other via single bonds to form a ring. In the general formulas (TEMP-53) to (TEMP-62) above, * represents a bond position.
[0091] [ka]
[0092] In the general formulas (TEMP-63) to (TEMP-68) above, Q1 to Q8 are each independently a hydrogen atom or a substituent. In the general formulas (TEMP-63) to (TEMP-68) above, * represents a bond position.
[0093] Unless otherwise specified herein, the substituted or unsubstituted divalent heterocyclic groups described herein are preferably any of the following general formulas (TEMP-69) to (TEMP-102).
[0094] [ka]
[0095] [ka]
[0096] [ka]
[0097] In the general formulas (TEMP-69) to (TEMP-82) above, Q1 to Q9 are each independently a hydrogen atom or a substituent.
[0098] [ka]
[0099] [ka]
[0100] [ka]
[0101] [ka]
[0102] In the general formulas (TEMP-83) to (TEMP-102) above, Q1 to Q8 are each independently a hydrogen atom or a substituent.
[0103] The above is a description of the substituents described herein.
[0104] • "When they combine to form a ring" In this specification, the phrase "one or more pairs of adjacent elements join together to form a substituted or unsubstituted monoring, join together to form a substituted or unsubstituted fused ring, or do not join together" means the case where "one or more pairs of adjacent elements join together to form a substituted or unsubstituted monoring," the case where "one or more pairs of adjacent elements join together to form a substituted or unsubstituted fused ring," and the case where "one or more pairs of adjacent elements do not join together." In this specification, the cases in which "one or more pairs of adjacent elements bond to each other to form a substituted or unsubstituted monoring" and "one or more pairs of adjacent elements bond to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "cases where elements bond to form a ring") will be explained below. An example will be given of an anthracene compound represented by the following general formula (TEMP-103), whose parent skeleton is an anthracene ring.
[0105] [ka]
[0106] For example, R921 ~R 930 In the case where "one or more pairs of adjacent groups are joined together to form a ring," the pairs of adjacent groups that make up one set are R 921 and R 922 The pair, R 922 and R 923 The pair, R 923 and R 924 The pair, R 924 and R 930 The pair, R 930 and R 925 The pair, R 925 and R 926 The pair, R 926 and R 927 The pair, R 927 and R 928 The pair, R 928 and R 929 The pair with, and R 929 and R 921 They are a pair.
[0107] The phrase "one or more pairs" above means that two or more pairs of adjacent pairs may simultaneously form a ring. For example, R 921 and R 922 and are joined to form a ring Q A Forms R 925 and R 926 and are joined to form a ring Q B If the above general formula (TEMP-103) is formed, the anthracene compound represented by the above general formula (TEMP-104) is represented by the following general formula (TEMP-104).
[0108] [ka]
[0109] The case where "two or more adjacent elements form a ring" includes not only cases where two adjacent elements are joined, as in the example above, but also cases where three or more adjacent elements are joined. For example, R 921 and R 922 and are joined to form a ring Q A Forms R 922 and R923 and are joined to form a ring Q C It forms three adjacent (R 921 , R 922 and R 923 This refers to the case where a set consisting of ) is bonded to each other to form a ring and condenses onto the anthracene matrix skeleton, in which case the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C R 922 Share.
[0110] [ka]
[0111] The formed "mono-ring" or "condensed-ring" may be saturated or unsaturated, based solely on the structure of the formed ring. Even when "a pair of adjacent rings" forms a "mono-ring" or "condensed-ring," the "mono-ring" or "condensed-ring" can be saturated or unsaturated. For example, ring Q formed in the general formula (TEMP-104) A and ring Q B These are, respectively, a "single ring" or a "condensed ring". Also, ring Q formed in the general formula (TEMP-105) is A , and ring Q C This is a "condensed ring". The ring Q of the general formula (TEMP-105) A and Q C This refers to the Q environment. A and Q C The ring Q of the general formula (TMEP-104) is formed by the condensation of the two rings. A If it is a benzene ring, then ring Q A It is a single ring. The ring Q of the general formula (TMEP-104) A If it is a naphthalene ring, then ring Q A It is a condensed ring.
[0112] An "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocycle. A "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocycle. Specific examples of aromatic hydrocarbon rings include structures in which the groups listed as examples in specific example group G1 are terminated by hydrogen atoms. A concrete example of an aromatic heterocycle is the structure in which the aromatic heterocycle group listed as a concrete example in concrete example group G2 is terminated by a hydrogen atom. Specific examples of aliphatic hydrocarbon rings include structures in which the groups listed as examples in example group G6 are terminated by hydrogen atoms. "To form a ring" means to form a ring with only multiple atoms of the parent skeleton, or with multiple atoms of the parent skeleton and one or more additional arbitrary elements. For example, as shown in the general formula (TEMP-104), 921 and R 922 A ring Q is formed when these two elements are bonded together. A R 921 The carbon atoms of the anthracene skeleton to which R is bonded, 922 It refers to a ring formed by the carbon atoms of the anthracene skeleton to which the R atoms are bonded, and one or more arbitrary elements. A specific example is R 921 and R 922 And the environment Q A When forming R 921 The carbon atoms of the anthracene skeleton to which R is bonded, 922 When the carbon atoms of the anthracene skeleton bonded to the four carbon atoms form a monocyclic unsaturated ring, R 921 and R 922 The ring formed by these two is a benzene ring.
[0113] Here, "any element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur, unless otherwise specified herein. In any element (for example, carbon or nitrogen), bonds that do not form a ring may be terminated with a hydrogen atom or the like, or substituted with "any substituent" as described later. If any element other than carbon is included, the formed ring is a heterocycle. The "one or more arbitrary elements" constituting the monoring or fused ring are preferably 2 to 15, more preferably 3 to 12, and even more preferably 3 to 5, unless otherwise specified herein. Unless otherwise specified herein, the preferred form is a "mono-ring" and a "condensed ring." Unless otherwise specified herein, the "unsaturated ring" is preferred over the "saturated ring". Unless otherwise specified herein, “monocyclic” is preferably a benzene ring. Unless otherwise specified herein, the “unsaturated ring” is preferably a benzene ring. When "one or more sets of two or more adjacent elements" "bond to each other to form a substituted or unsubstituted monoring" or "bond to each other to form a substituted or unsubstituted fused ring", unless otherwise specified herein, preferably, one or more sets of two or more adjacent elements bond to each other to form a substituted or unsubstituted "unsaturated ring" consisting of multiple atoms of the parent skeleton and at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur elements, ranging from one to fifteen.
[0114] When the above-mentioned "monocyclic ring" or "fused ring" has substituents, the substituents are, for example, "any substituents" as described later. Specific examples of substituents when the above-mentioned "monocyclic ring" or "fused ring" has substituents are the substituents described in the section "Substituents as described herein" above. When the above-mentioned "saturated ring" or "unsaturated ring" has substituents, the substituents are, for example, "any substituents" as described later. Specific examples of substituents when the above-mentioned "mono-ring" or "fused ring" has substituents are the substituents described in the section "Substituents as described herein" above. The above explains the cases in which "one or more pairs of adjacent elements combine to form a substituted or unsubstituted monoring" and "one or more pairs of adjacent elements combine to form a substituted or unsubstituted fused ring" ("the case of combining to form a ring").
[0115] • Substituents in the phrase "substituted or unsubstituted" In one embodiment described herein, the substituent referred to as "substituted or unsubstituted" (which may be referred to herein as "any substituent") is, for example, Unsubstituted alkyl groups with 1 to 50 carbon atoms, Unsubstituted alkenyl groups with 2 to 50 carbon atoms, Unsubstituted alkynyl groups with 2 to 50 carbon atoms, Unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, Unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, and These are groups selected from the group consisting of unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms, Here, R 901 ~R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, It is a substituted or unsubstituted aryl group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 ring-forming atoms. R 901 If there are two or more of them, then there are two or more R 901 They are either identical or different from each other. R 902 If there are two or more of them, then there are two or more R 902 They are either identical or different from each other. R 903 If there are two or more of them, then there are two or more R903 They are either identical or different from each other. R 904 If there are two or more of them, then there are two or more R 904 They are either identical or different from each other. R 905 If there are two or more of them, then there are two or more R 905 They are either identical or different from each other. R 906 If there are two or more of them, then there are two or more R 906 They are either identical or different from each other. R 907 If there are two or more of them, then there are two or more R 907 They are either identical or different from one another.
[0116] In one embodiment, the substituent in the case of "substituted or unsubstituted" is: Alkyl alkyl groups with 1 to 50 carbon atoms, A ring-forming aryl group with 6 to 50 carbon atoms, and It is a group selected from the group consisting of heterocyclic groups with 5 to 50 ring-forming atoms.
[0117] In one embodiment, the substituent in the case of "substituted or unsubstituted" is: Alkyl alkyl groups with 1 to 18 carbon atoms, Ring-forming aryl groups with 6 to 18 carbon atoms, and It is a group selected from the group consisting of heterocyclic groups with 5 to 18 ring-forming atoms.
[0118] Specific examples of each of the above-mentioned substituents are the specific examples of substituents described in the section "Substituents as described herein" above.
[0119] Unless otherwise specified herein, adjacent substituents may form a "saturated ring" or an "unsaturated ring," preferably a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, and more preferably a benzene ring. Unless otherwise specified herein, any substituent may have further substituents, such as those described above.
[0120] In this specification, a numerical range expressed using "AA~BB" means a range that includes the numerical value AA, which is listed before "AA~BB", as the lower limit, and the numerical value BB, which is listed after "AA~BB", as the upper limit.
[0121] [First Embodiment] (compound) The compound according to this embodiment has at least one group represented by the following general formula (110) and is a compound represented by the following general formula (1000B).
[0122] [ka]
[0123] (In the above general formula (1000B), X consists of an oxygen atom, a sulfur atom, and C(R). 2001 )(R 2002 ), or Si(R 2003 )(R 2004 ) and R 10 ~R 19 Of these, one or more pairs consisting of two or more adjacent items, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 10 ~R 19 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Nitro group, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, or The group is represented by the general formula (110) above, However, R 10 ~R 19 At least one of them is a group represented by the general formula (110), If there are multiple groups represented by the general formula (110), the multiple groups represented by the general formula (110) may be identical or different from each other. L 100 teeth, single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, mx is 1, 2, or 3. L 100 If there are 2 or more, then 2 or more L 100 They are either identical or different from each other. Ar 100 teeth, A substituted or unsubstituted aryl group containing three or more rings, or A substituted or unsubstituted heterocyclic group comprising two or more aromatic rings and one or more heterocyclic rings, Ar 100 It does not contain an anthracene ring, Ar 100 If there are 2 or more Ar 100 They are either identical or different from each other. In the general formula (110) above, * indicates the bond position.
[0124] The compound represented by the general formula (1000B) preferably has at least one group represented by the general formula (110) and is a compound represented by the following general formula (100).
[0125] [ka]
[0126] (In the above general formula (100), R 10 ~R 19 Each of these independently corresponds to R in the general formula (1000B) 10 ~R 19 It is synonymous with R 10 ~R 19 Of these, any set consisting of two or more adjacent items does not combine with each other, Ar 100 , L 100 and mx are, respectively, Ar in the general formula (110). 100 , L 100 (And it is synonymous with MX.)
[0127] The LUMO (Lowest Unoccupied Molecular Orbital) of compounds in which a cyano group is directly bonded to a benzoxanthene ring (referred to as cyano-substituted benzoxanthene compounds) is lower than that of compounds in which the cyano group is not bonded to a benzoxanthene ring. When cyano-substituted benzoxanthene compounds are used as the host material for the light-emitting layer, damage to the host material at the interface on the hole transport layer side of the light-emitting layer may increase, potentially reducing the lifespan of the organic EL device. In particular, it is unsuitable to use cyano-substituted benzoxanthene compounds in the light-emitting layer on the hole transport layer side of an organic EL device in which multiple light-emitting layers are stacked.
[0128] The compound according to this embodiment may also be represented by the following general formula (101) or general formula (102).
[0129] [ka]
[0130] [ka]
[0131] (In the above general formulas (101) and (102), R 10 ~R 19 Each of these independently corresponds to R in the general formula (1000B) 10 ~R 19 It is synonymous with R 10 ~R 19 Of these, any set consisting of two or more adjacent items does not combine with each other, Ar 100 , L 100 and mx are, respectively, Ar in the general formula (110). 100 , L 100 (And it is synonymous with MX.)
[0132] In the compound according to this embodiment, R is not a group represented by the general formula (110). 10 ~R 19Preferably, each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, or a substituted or unsubstituted ring-forming C6-C50 aryl group.
[0133] In the compound according to this embodiment, R is not a group represented by the general formula (110). 10 ~R 19 It is preferable that it be a hydrogen atom.
[0134] In the compound according to this embodiment, L 100 It is preferable that the arylene group contains three or fewer single-bonded, substituted, or unsubstituted benzene rings.
[0135] In the compound according to this embodiment, L 100 It is preferable that the anthreylene group is neither substituted nor unsubstituted.
[0136] In the compound according to this embodiment, L 100 It is also preferable that the bond be a single bond.
[0137] In the compound according to this embodiment, -(L in the general formula (110) 100 ) mx It is also preferable that the group represented by - is a group represented by any of the following general formulas (111) to (120).
[0138] [ka]
[0139] [ka]
[0140] (In general formulas (111) to (120) above, * indicates the bond position.)
[0141] -(L in the above general formula (110) 100) mx It is preferable that the group represented by - is the group represented by the general formula (111) or (112).
[0142] In the compound according to this embodiment, Ar 100 It is preferable that the aryl group is formed by the condensation of four or more substituted or unsubstituted benzene rings.
[0143] In the compound according to this embodiment, Ar 100 Preferably, this is an aryl group formed by the condensation of four substituted or unsubstituted benzene rings, or an aryl group formed by the condensation of five substituted or unsubstituted benzene rings.
[0144] In the compound according to this embodiment, Ar 100 Preferably, the group is represented by the following general formulas (1100), (1200), (1300), (1400), (1500), (1600), (1700), or (1800).
[0145] [ka]
[0146] [ka]
[0147] [ka]
[0148] [ka]
[0149] (In the above general formula (1100), R 111 ~R 120 One of them is a joint, In the above general formula (1200), R 1201 ~R 1212 One of them is a joint, In the above general formula (1300), R 1301 ~R 1314 One of them is a joint, In the above general formula (1400), R 1401 ~R 1414 One of them is a joint, In the above general formula (1500), R 1501 ~R 1514 One of them is a joint, In the above general formula (1600), R 1601 ~R 1612 One of them is a joint, In the above general formula (1700), R 1701 ~R 1710 One of them is a joint, In the above general formula (1800), R 1801 ~R 1812 One of them is a joint, R is not a joint 111 ~R 120 , not a joint R 1201 ~R 1212 , not a joint R 1301 ~R 1314 , not a joint R 1401 ~R 1414 , not a joint R 1501 ~R 1514 , not a joint R 1601 ~R 1612 , not a joint R 1701 ~R 1710 , as well as R which is not a joint 1801 ~R 1812 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0150] The group represented by the general formula (1100) is R 111 If it is a bond, it is a group represented by the following general formula (1112), and R 120 If it is a bond, it is a group represented by the following general formula (1113), and R 119 When it is a bond, it is a group represented by the following general formula (1114).
[0151] [ka]
[0152] (In the above general formulas (1112), (1113), and (1114), R 111 ~R 120 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. In the general formulas (1112) to (1114) above, the asterisk (*) indicates the bond position.
[0153] In the compound according to this embodiment, R is not a bond. 111 ~R 120 , not a joint R 1201 ~R 1212 , not a joint R 1301 ~R 1314 , not a joint R 1401 ~R 1414 , not a joint R 1501 ~R 1514 , not a joint R 1601 ~R 1612 , not a joint R 1701 ~R 1710 , as well as R which is not a joint 1801 ~R 1812 Preferably, each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, or a substituted or unsubstituted ring-forming C6-C50 aryl group.
[0154] In the compound according to this embodiment, R is not a bond. 111 ~R 120 , not a joint R 1201 ~R 1212 , not a joint R 1301 ~R 1314 , not a joint R 1401 ~R 1414 , not a joint R 1501 ~R 1514 , not a joint R 1601 ~R 1612 , not a joint R 1701 ~R 1710 , as well as R which is not a joint 1801 ~R 1812 It is preferable that it be a hydrogen atom.
[0155] In the compound according to this embodiment, Ar is used as a substituted or unsubstituted heterocyclic group comprising two or more aromatic rings and one or more heterocyclic rings. 100 It is also preferable that this group be, for example, a substituted or unsubstituted benzoxanthenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group.
[0156] The compounds according to this embodiment preferably do not contain cyano groups in their molecules.
[0157] The compound according to this embodiment may also preferably contain only one or two benzoxanthene rings in its molecule. Furthermore, the compound according to this embodiment may preferably contain only one benzoxanthene ring in its molecule.
[0158] The compound according to this embodiment preferably has at least one group represented by the following general formula (11) and contains only one benz[de]anthracene derivative skeleton represented by the following general formula (1000) in its molecule.
[0159] [ka]
[0160] (In the above general formula (1000), X consists of an oxygen atom, a sulfur atom, and C(R). 2001 )(R 2002 ), or Si(R 2003 )(R 2004 ) and R 10 ~R 19 Of these, one or more pairs consisting of two or more adjacent items, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 10 ~R 19 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Nitro group, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, or The group is represented by the general formula (11) above, However, R 10 ~R 19 At least one of them is a group represented by the general formula (11), If there are multiple groups represented by the general formula (11), the multiple groups represented by the general formula (11) may be identical or different from each other. L1 is A substituted or unsubstituted ring-forming arylene group with 6 to 15 carbon atoms, or A divalent heterocyclic group having 5 to 15 substituted or unsubstituted ring-forming atoms, mx is 1, 2, or 3. If there are two or more L1s, then the two or more L1s are either identical or different from each other. Ar1 is a substituted or unsubstituted aryl group containing four or more rings. If there are two or more Ar1s, then the two or more Ar1s are either identical or different from each other. In the general formula (11) above, * indicates the bond position.
[0161] The compound represented by the general formula (1000) preferably has at least one group represented by the general formula (11) and contains only one benzoxanthene ring represented by the following general formula (1) in its molecule.
[0162] [ka]
[0163] (In the above general formula (1), R 10 ~R 19 Each of these independently corresponds to R in the general formula (1000) above. 10 ~R 19 It is synonymous with R 10 ~R 19Of these, any set consisting of two or more adjacent elements does not combine with each other, and Ar1, L1, and mx are equivalent to Ar1, L1, and mx in the general formula (11), respectively.
[0164] The compound represented by the general formula (1) has a benzoxanthene ring and an Ar1 which is a substituted or unsubstituted aryl group containing four or more rings, between which is an arylene group having 6 to 15 ring-forming carbon atoms, or an L1 which is a divalent heterocyclic group having 5 to 15 ring-forming atoms, thereby suppressing a decrease in hole mobility and also suppressing a decrease in the luminous efficiency of organic EL devices.
[0165] A 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 its molecule is preferably represented by the following general formula (121) or general formula (122).
[0166] [ka]
[0167] [ka]
[0168] (In the above general formulas (121) and (122), R 10 ~R 19 Each of these independently corresponds to R in the general formula (1) above. 10 ~R 19 This is synonymous with Ar1, L1, and mx, respectively, and they are equivalent to Ar1, L1, and mx in the general formula (11) above.
[0169] In the above general formula (121), R 10 ~R 12 , R 14 ~R 19 Preferably, the group is not one represented by the general formula (11). In the above general formula (122), R 10 ~R17 , R 19 Preferably, the group is not one represented by the general formula (11).
[0170] In the compound represented by the general formula (1), R is not a group represented by the general formula (11). 10 ~R 19 Preferably, each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, or a substituted or unsubstituted ring-forming C6-C50 aryl group.
[0171] In the compound represented by the general formula (1), R is not a group represented by the general formula (11). 10 ~R 19 It is preferable that it be a hydrogen atom.
[0172] In the compound represented by the general formula (1) above, L1 is preferably an arylene group containing three or fewer substituted or unsubstituted benzene rings.
[0173] In the compound represented by the general formula (1) above, it is preferable that L1 is not a substituted or unsubstituted anthreylene group.
[0174] In the compound represented by the general formula (1) above, -(L1) in the general formula (11) mx It is also preferable that the group represented by - is a group represented by any of the general formulas (111) to (120).
[0175] In the compound represented by the general formula (1) above, -(L1) in the general formula (11) mx It is preferable that the group represented by - is the group represented by the general formula (111) or (112).
[0176] A compound having at least one group represented by the general formula (11) and containing only one benz[de]anthracene derivative skeleton represented by the general formula (1000) in its molecule may also preferably be represented by the following general formulas (123), (124), (125), or (126).
[0177] [ka]
[0178] [ka]
[0179] [ka]
[0180] [ka]
[0181] In the above general formulas (123), (124), (125), and (126), X consists of an oxygen atom, a sulfur atom, and C(R). 2001 )(R 2002 ), or Si(R 2003 )(R 2004 ) and R 2001 ~R 2004 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. L 10 teeth, A substituted or unsubstituted ring-forming arylene group with 6 to 15 carbon atoms, or A divalent heterocyclic group having 5 to 15 substituted or unsubstituted ring-forming atoms, Ar 10 This is an aryl group formed by the condensation of four or more substituted or unsubstituted benzene rings. Ar 11 These are substituted or unsubstituted ring-forming aryl groups with 6 to 14 carbon atoms. However, Ar 11 This is not a substituted or unsubstituted anthryl group, m10 is 5, m11 is 6, Rm is independent of each other. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. Multiple Rm values do not combine with each other. R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another. R 801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 They are either identical or different from one another.
[0182] As with the compounds represented by the general formula (123) and the compounds represented by the general formula (125), the benz[de]anthracene derivative skeleton contains Ar 11 By substituting (a substituted or unsubstituted aryl group with 6 to 14 ring-forming carbon atoms, other than a substituted or unsubstituted anthryl group), the singlet energy S1 is reduced, and the excited state is expected to be stabilized, thus potentially extending the lifespan of devices using this compound. Furthermore, as with the compounds represented by the general formula (124) and the compounds represented by the general formula (126), Ar 10 (Aryl group formed by the condensation of four or more substituted or unsubstituted benzene rings) 11 Substitution with substituted or unsubstituted aryl groups with 6 to 14 carbon atoms (other than substituted or unsubstituted anthryl groups) improves electron transport properties, and is expected to improve the carrier balance of devices using the compound.
[0183] The compound represented by the general formula (123) is more preferably represented by the following general formula (1230). Furthermore, the compound represented by the general formula (124) is more preferably represented by the following general formula (1240). Furthermore, the compound represented by the general formula (125) is more preferably represented by the following general formula (1250). Furthermore, the compound represented by the general formula (126) is more preferably represented by the following general formula (1260).
[0184] [ka]
[0185] [ka]
[0186] [ka]
[0187] [ka]
[0188] In the above general formulas (1230), (1240), (1250), and (1260), X, L 10 Ar 10 Ar 11 m10, m11, and Rm are each independently L in the general formulas (123), (124), (125), and (126). 10 Ar 10 Ar 11 This is synonymous with m10, m11, and Rm.
[0189] In the compounds represented by the general formulas (123), (124), (125), (126), (1230), (1240), (1250), or (1260), X is preferably an oxygen atom.
[0190] In the compounds represented by the general formulas (123), (124), (125), (126), (1230), (1240), (1250), or (1260), L 10 It is preferable that the arylene group contains three or fewer substituted or unsubstituted benzene rings.
[0191] In the compounds represented by the general formulas (123), (124), (125), (126), (1230), (1240), (1250), or (1260), -L 10 It is preferable that the group represented by - is a group represented by any of the general formulas (111) to (120).
[0192] In the compounds represented by the general formulas (123), (124), (125), (126), (1230), (1240), (1250), or (1260), -L 10 It is preferable that the group represented by - is the group represented by the general formula (111) or (112).
[0193] The compound according to this embodiment preferably has at least one group represented by the following general formula (110A) and contains only one benz[de]anthracene derivative skeleton represented by the following general formula (1000A) in its molecule.
[0194] [ka]
[0195] (In the above general formula (1000A), X consists of an oxygen atom, a sulfur atom, and C(R). 2001 )(R 2002 ), or Si(R 2003 )(R 2004 ) and R 10 ~R 19 Of these, one or more pairs consisting of two or more adjacent items, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 10 ~R 19 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Nitro group, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, or The group is represented by the general formula (110A) mentioned above, However, R 13 and R 18 At least one of these is a group represented by the general formula (110A), If there are multiple groups represented by the general formula (110A), the multiple groups represented by the general formula (110A) may be identical or different from each other. L 100 teeth, single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, mx is 1, 2, or 3. L 100 If there are 2 or more, then 2 or more L 100 They are either identical or different from each other. Ar1 is a substituted or unsubstituted aryl group containing four or more rings. If there are two or more Ar1s, then the two or more Ar1s are either identical or different from each other. In the general formula (110A) above, * indicates the bond position.
[0196] The compound represented by the general formula (1000A) preferably has at least one group represented by the general formula (110A) and contains only one benzoxanthene ring represented by the following general formula (100A) in its molecule.
[0197] [ka]
[0198] (In the above general formula (100A), R 10 ~R 19 Each of these independently corresponds to R in the general formula (1000A) 10 ~R 19 It is synonymous with R 10 ~R 19 Of these, any set consisting of two or more adjacent elements does not combine with each other, and Ar1, L1, and mx are equivalent to Ar1, L1, and mx in the general formula (110A), respectively.
[0199] In the compound represented by the general formula (100A), R 13 and R 18At least one of these groups contains Ar1, which is a substituted or unsubstituted aryl group containing four or more rings. In this way, Ar1 is bonded to the para position of the oxygen atom (O) of the benzoxanthene ring via a single bond, a substituted or unsubstituted arylene group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group with 5 to 50 ring-forming atoms, thereby improving the hole implantation properties of the compound according to this embodiment. Therefore, an improvement in the luminescence efficiency of organic EL devices using the compound according to this embodiment can be expected.
[0200] The compound represented by the general formula (100A) may also be represented by the following general formula (121A) or general formula (122A).
[0201] [ka]
[0202] [ka]
[0203] (In the above general formulas (121A) and (122A), R 10 ~R 19 Each of these independently corresponds to R in the general formula (100A) 10 ~R 19 It is synonymous with Ar1, L 100 and mx are Ar1 and L in the general formula (110A), respectively. 100 (And it is synonymous with MX.)
[0204] In the above general formula (121A), R 10 ~R 12 , R 14 ~R 19 Preferably, the group is not represented by the general formula (110A). In the above general formula (122A), R 10 ~R 17 , R 19 Preferably, the group is not represented by the general formula (110A).
[0205] In the compound represented by the general formula (100A), R is not a group represented by the general formula (110A). 10 ~R 19 Preferably, each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, or a substituted or unsubstituted ring-forming C6-C50 aryl group.
[0206] In the compound represented by the general formula (100A), R is not a group represented by the general formula (110A). 10 ~R 19 It is preferable that it be a hydrogen atom.
[0207] In the compound represented by the general formula (100A), L 100 It is preferable that the arylene group contains three or fewer single-bonded, substituted, or unsubstituted benzene rings.
[0208] In the compound represented by the general formula (100A), -(L 100 ) mx It is preferable that the group represented by - is a group represented by any of the general formulas (111) to (120).
[0209] In the compound represented by the general formula (100A), -(L 100 ) mx It is preferable that the group represented by - is the group represented by the general formula (111) or (112).
[0210] In the compound according to this embodiment, Ar1 is preferably an aryl group formed by the condensation of four or more substituted or unsubstituted benzene rings.
[0211] In the compound according to this embodiment, Ar1 or Ar 10 Preferably, this is an aryl group formed by the condensation of four substituted or unsubstituted benzene rings, or an aryl group formed by the condensation of five substituted or unsubstituted benzene rings.
[0212] In the compound according to this embodiment, Ar1 or Ar 10 Preferably, the group is represented by the general formulas (1100), (1200), (1300), (1400), (1500), (1600), (1700), or (1800).
[0213] In the compound according to this embodiment, Ar1 or Ar 10 Preferably, the group is represented by the general formula (1100) or (1200).
[0214] In the compounds according to this embodiment, it is preferable that any group described as "substituted or unsubstituted" is an "unsubstituted" group.
[0215] Among the compounds according to this embodiment (compounds represented by the general formula (1000B), compounds represented by the general formula (1000), compounds represented by the general formula (1000A), etc.), R 10 ~R 19 In the case where "one or more pairs of adjacent elements combine to form a ring (a substituted or unsubstituted monoring or a substituted or unsubstituted fused ring)", an adjacent pair of elements is, for example, R 10 and R 11 The pair, R 11 and R 12 The pair, R 12 and R 13 The pair, R 13 and R 14 The pair, R 14 and R 15 The pair, R 16 and R 17 The pair, R 17 and R 18 The pair, R 18 and R 19 The pair with, and R 19 and R 10 They are a pair.
[0216] Among the compounds according to this embodiment (compounds represented by the general formula (1000B), compounds represented by the general formula (1000), compounds represented by the general formula (1000A), etc.), R 13 and R 14 The pair, R 16 and R 17 The pair with, and R 19 and R 10 It is preferable that either of the pairs combine with each other to form a substituted or unsubstituted benzene ring.
[0217] Among the compounds according to this embodiment (compounds represented by the general formula (1000B), compounds represented by the general formula (1000), compounds represented by the general formula (1000A), etc.), R 2001 ~R 2004 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms.
[0218] Among the compounds according to this embodiment (compounds represented by the general formula (1000B), compounds represented by the general formula (1000), compounds represented by the general formula (1000A), etc.), R 2001 ~R 2004 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is preferable that the heterocyclic group has 5 to 50 substituted or unsubstituted ring-forming atoms.
[0219] Among the compounds according to this embodiment (compounds represented by the general formula (1000B), compounds represented by the general formula (1000), compounds represented by the general formula (1000A), etc.), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another. R 801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 They are either identical or different from one another.
[0220] The hydrogen atoms in the compound according to this embodiment are light hydrogen atoms, deuterium atoms, or tritium atoms. In one embodiment, the hydrogen atoms in the compound according to this embodiment are light hydrogen atoms. In one embodiment, the hydrogen atoms in the compound according to this embodiment are deuterium atoms.
[0221] • Method for producing the compound according to this embodiment The compounds according to this embodiment can be produced by following the synthesis method described in the examples below, or by using known alternative reactions and raw materials tailored to the target product, in accordance with that synthesis method.
[0222] • Specific examples of compounds according to this embodiment Specific examples of compounds according to this embodiment include, for example, the following compounds. However, the present invention is not limited to these specific examples. In this specification, deuterium atoms are denoted as D in chemical formulas, and light hydrogen atoms are denoted as H or omitted from the description.
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[0452] The compound according to this embodiment can improve the performance of organic EL elements. Furthermore, when the compound according to this embodiment is used in the anode-side light-emitting layer (first light-emitting layer) of an organic EL element in which multiple light-emitting layers are stacked, it is expected that an element with a good balance between luminous efficiency and lifespan will be provided.
[0453] [Second Embodiment] (Materials for organic electroluminescent devices) The material for an organic electroluminescent device according to this embodiment contains the compound according to the first embodiment. One embodiment is a material for an organic electroluminescent device that contains only the compound according to the first embodiment, and another embodiment is a material for an organic electroluminescent device that contains the compound according to the first embodiment and other compounds different from the compound in the first embodiment. In the organic electroluminescent element material of this embodiment, it is preferable that the compound according to the first embodiment is the host material. In this case, the organic electroluminescent element material may include the compound according to the first embodiment as the host material and other compounds such as dopant materials.
[0454] [Third Embodiment] [Organic electroluminescent element] The organic EL element according to this embodiment will be described below. The organic EL element according to this embodiment includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. This organic layer includes at least one layer composed of an organic compound. Alternatively, this organic layer is formed by laminating multiple layers composed of organic compounds. The organic layer may further contain an inorganic compound.
[0455] In the organic EL element according to this embodiment, at least one layer of the organic layer contains the compound according to the first embodiment.
[0456] In the organic EL element of this embodiment, it is preferable that at least one of the organic layers is an emissive layer. In the organic EL element of this embodiment, it is preferable that the emissive layer contains the compound according to the first embodiment. In one embodiment, the emissive layer contains the compound represented by the general formula (100). In one embodiment, the emissive layer contains the compound represented by the general formula (1). In one embodiment, the emissive layer contains the compound represented by the general formula (100A).
[0457] In one embodiment, the light-emitting layer may contain a metal complex. In one embodiment, it is also preferable that the light-emitting layer does not contain a metal complex. In one embodiment, it is preferable that the light-emitting layer does not contain phosphorescent material (dopant material). Furthermore, in one embodiment, it is preferable that the luminescent layer does not contain heavy metal complexes and phosphorescent rare earth metal complexes. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.
[0458] The organic layer may consist of, for example, a single light-emitting layer, or it may include layers that can be used in an organic EL device. The layers that can be used in an organic EL device are not particularly limited, but examples include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a barrier layer.
[0459] In this embodiment, it is preferable that the organic EL element has a hole transport layer between the anode and the light-emitting layer.
[0460] In this embodiment, it is preferable that the organic EL element has an electron transport layer between the cathode and the light-emitting layer.
[0461] In the organic EL element according to this embodiment, the organic layer may be composed of a plurality of light-emitting layers. For example, the organic layer may be composed of two light-emitting layers, a first light-emitting layer and a second light-emitting layer. In addition to the first light-emitting layer and the second light-emitting layer, the organic EL element according to this embodiment may have one or more organic layers, and may further have at least one layer selected from the group consisting of, for example, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole barrier layer, and an electron barrier layer.
[0462] In the organic EL element according to this embodiment, it is also preferable that the organic layer has a first light-emitting layer and a second light-emitting layer. In one embodiment, the first light-emitting layer is positioned between the anode and the cathode, and the second light-emitting layer is positioned between the first light-emitting layer and the cathode. In another embodiment, the second light-emitting layer is positioned between the anode and the cathode, and the first light-emitting layer is positioned between the second light-emitting layer and the cathode. In the organic EL element according to this embodiment, the first light-emitting layer and the second light-emitting layer can be positioned in any of the above embodiments. In the organic EL element according to this embodiment, the first light-emitting layer and the second light-emitting layer may or may not be in direct contact.
[0463] An organic EL element according to one embodiment includes an anode, a cathode, a first light-emitting layer disposed between the anode and the cathode, and a second light-emitting layer disposed between the first light-emitting layer and the cathode, wherein the first light-emitting layer contains a first compound, the first compound having at least one group represented by the general formula (110) and being a compound represented by the general formula (100), and the first light-emitting layer and the second light-emitting layer are in direct contact.
[0464] In the organic EL element according to this embodiment, if the organic layer has an emissive layer, it is preferable to have an electron transport layer between the cathode and the emissive layer. If the emissive layer has a first emissive layer and a second emissive layer, in one embodiment, an electron transport layer may be provided between the cathode and the second emissive layer. In the organic EL element according to this embodiment, if the organic layer has an emissive layer, it is preferable to have a hole transport layer between the anode and the emissive layer. If the emissive layer has a first emissive layer and a second emissive layer, in one embodiment, a hole transport layer may be provided between the anode and the first emissive layer.
[0465] In the organic EL element according to this embodiment, a non-doped region that does not contain a third fluorescent compound can also be provided on the anode side of the first light-emitting layer. Furthermore, the organic EL element according to this embodiment may have a first light-emitting layer, a second light-emitting layer, and an undoped region disposed between the anode and the first light-emitting layer. The undoped region may be, for example, an undoped organic layer in direct contact with the anode side of the first light-emitting layer. The undoped organic layer does not contain metal atoms, and the content of each of the materials constituting the undoped organic layer is preferably 10% by mass or more, and more preferably more than 10% by mass. The undoped organic layer preferably contains the compound according to the first embodiment. The undoped organic layer may also consist only of the compound according to the first embodiment. The undoped organic layer is, for example, a second hole transport layer or an electron barrier layer.
[0466] Figure 1 shows a schematic configuration of an example of an organic EL element according to this embodiment. 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 constructed by stacking, in the following order from the anode 3 side: a hole injection layer 6, a hole transport layer 7, a first light-emitting layer 51, a second light-emitting layer 52, an electron transport layer 8, and an electron injection layer 9.
[0467] (First light-emitting layer) In the organic EL element according to this embodiment, the first light-emitting layer preferably contains a first compound. The first compound is preferably a first host material. In the organic EL element according to this embodiment, the first light-emitting layer may further contain a third fluorescent compound. The first light-emitting layer may also contain a first compound as a first host material and a third compound as a first dopant material.
[0468] In this specification, "host material" refers to a material that makes up, for example, "50% by mass or more of the layer." Therefore, for example, the first light-emitting layer contains the first compound in an amount of 50% by mass or more of the total mass of the first light-emitting layer. Alternatively, for example, the "host material" may make up 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.
[0469] (First compound) In the organic EL element according to this embodiment, the first compound is the compound according to the first embodiment. In an organic EL element according to one embodiment, the first compound is a compound having at least one group represented by the general formula (110) and also represented by the general formula (1000B). In an organic EL element according to one embodiment, the first compound is a compound having at least one group represented by the general formula (11) and containing only one benz[de]anthracene derivative skeleton represented by the general formula (1000) in its molecule. In an organic EL element according to one embodiment, the first compound is a compound having at least one group represented by the general formula (110A) and containing only one benz[de]anthracene derivative skeleton represented by the general formula (1000A) in its molecule.
[0470] (Second light-emitting layer) In the organic EL element according to this embodiment, the second light-emitting layer preferably contains a second compound. The second compound is preferably a second host material. In the organic EL element according to this embodiment, the second light-emitting layer may further contain a fluorescent fourth compound. The second light-emitting layer may also contain a second compound as a second host material and a fourth compound as a second dopant material. If the first light-emitting layer contains the third compound and the second light-emitting layer contains the fourth compound, then the third compound and the fourth compound are either identical or different from each other.
[0471] (Second compound) In the organic EL element according to this embodiment, the second compound is not particularly limited. Examples of the second compound as a host material in the organic EL element according to this embodiment include heterocyclic compounds and condensed aromatic compounds. Examples of condensed aromatic compounds include anthracene derivatives, pyrene derivatives, and benzanthracene derivatives.
[0472] The second compound may also preferably be a compound represented by the following general formula (2).
[0473] [ka]
[0474] (In the above general formula (2), R 201 ~R 208 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. L 201 and L 202 Each of them operates independently. single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, Ar 201 and Ar 202 Each of them operates independently. A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0475] (In the second compound according to this embodiment, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another. R 801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 They are either identical or different to one another.
[0476] In the organic EL element according to this embodiment, R 201 ~R 208 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, or It is a nitro group, L 201 and L 202 Each of them operates independently. single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, Ar 201 and Ar 202 Each of them operates independently. A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is preferable that the heterocyclic group has 5 to 50 substituted or unsubstituted ring-forming atoms.
[0477] In the second compound, R 201 ~R 208 Each of these independently consists of a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, or -Si(R 901 )(R 902 )(R 903 It is also preferable that the group be represented by ).
[0478] In the second compound, R 201 ~R 208 It is also preferable that it be a hydrogen atom.
[0479] In the organic EL element according to this embodiment, L 201 and L 202 Each of these is independently a single-bonded, substituted, or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, and Ar 201 and Ar 202 Preferably, each of these is independently a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.
[0480] In the organic EL element according to this embodiment, Ar 201 and Ar 202 Each of them operates independently. Phenyl group, Naphthyl group, Phenanthryl group, biphenyl group, Terphenyl group, diphenylfluorenyl group, Dimethylfluorenyl group, Benzodiphenylfluorenyl group, Benzodimethylfluorenyl group, Dibenzofuranyl group, dibenzothienyl group, Benzoxanthenyl group, Naphthobenzofuranyl group, or It is preferable that the group be a naphthobenzothienyl group.
[0481] In the organic EL element according to this embodiment, the second compound represented by general formula (2) is preferably a compound represented by the following general formulas (201), (202), (203), (204), (205), (206), (207), (208), or (209).
[0482] [ka]
[0483] [ka]
[0484] [ka]
[0485] [ka]
[0486] [ka]
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[0490] [ka]
[0491] (In the general formulas (201) to (209), L 201 and Ar 201 L in the general formula (2) above is 201 and Ar 201 It is synonymous with R 201 ~R 208 Each of these independently corresponds to R in the general formula (2) above. 201 ~R 208 (This is synonymous with...)
[0492] The second compound represented by the general formula (2) is also preferably a compound represented by the following general formulas (221), (222), (223), (224), (225), (226), (227), (228), or (229).
[0493] [ka]
[0494] [ka]
[0495] [ka]
[0496] [ka]
[0497] [ka]
[0498] [ka]
[0499] [ka]
[0500] [ka]
[0501] [ka]
[0502] (In the above general formulas (221), (222), (223), (224), (225), (226), (227), (228), and (229), R 201 R 203 ~R 208 Each of these independently corresponds to R in the general formula (2) above. 201 R 203 ~R 208 It is synonymous with, L 201 and Ar 201 These are, respectively, L in the general formula (2) above. 201 and Ar 201 It is synonymous with, L 203 L in the general formula (2) above is 201 It is synonymous with, L 203 and L 201 They are either identical or different from each other. Ar 203 This is Ar in the general formula (2) above. 201It is synonymous with, Ar 203 and Ar 201 They are either identical or different to one another.
[0503] The second compound represented by the general formula (2) is also preferably a compound represented by the following general formulas (241), (242), (243), (244), (245), (246), (247), (248), or (249).
[0504] [ka]
[0505] [ka]
[0506] [ka]
[0507] [ka]
[0508] [ka]
[0509] [ka]
[0510] [ka]
[0511] [ka]
[0512] [ka]
[0513] (In the above general formulas (241), (242), (243), (244), (245), (246), (247), (248), and (249), R 201 , R 202 R 204 ~R 208 Each of these independently corresponds to R in the general formula (2) above. 201 , R 202 R 204 ~R 208 It is synonymous with, L 201 and Ar 201 These are, respectively, L in the general formula (2) above. 201 and Ar 201 It is synonymous with, L 203 L in the general formula (2) above is 201 It is synonymous with, L 203 and L 201 They are either identical or different from each other. Ar 203 This is Ar in the general formula (2) above. 201 It is synonymous with, Ar 203 and Ar 201 They are either identical or different to one another.
[0514] In the second compound represented by the general formula (2) above, R 201 ~R 208 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 It is preferable that the group is represented by ).
[0515] L 101 teeth, Single bond, or It is an unsubstituted ring-forming arylene group with 6 to 22 carbon atoms. Ar 101 It is preferable that the ring-forming aryl group has 6 to 22 carbon atoms and is either substituted or unsubstituted.
[0516] In the organic EL element according to this embodiment, in the second compound represented by the general formula (2), R is a substituent of the anthracene skeleton. 201 ~R 208 It is preferable that the atom is a hydrogen atom in order to prevent the suppression of intermolecular interactions and to suppress the decrease in electron mobility, 201 ~R 208 This may be a substituted or unsubstituted aryl group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 ring-forming atoms. R 201 ~R 208 When the substituent is a bulky alkyl group or cycloalkyl group, intermolecular interactions are suppressed, reducing electron mobility to the first compound, and potentially failing to satisfy the relationship μH2 > μH1 described in the following formula (Equation 3). When the second compound is used as the second light-emitting layer, it is expected that the relationship μH2 > μH1 will be satisfied, thereby suppressing the decrease in the recombination ability of holes and electrons in the first light-emitting layer and the decrease in luminescence efficiency. The substituents include haloalkyl groups, alkenyl groups, alkynyl groups, and -Si(R 901 )(R 902 )(R 903 A group represented by -O-(R 904 A group represented by -S-(R 905 A group represented by -N(R 906 )(R 907 A group represented by ), an aralkyl group, -C(=O)R 801 The base represented by -COOR 802 The groups represented by, halogen atoms, cyano groups, and nitro groups may become bulkier, and alkyl groups and cycloalkyl groups may become even bulkier. In the second compound represented by the general formula (2), R is a substituent of the anthracene skeleton. 201 ~R 208 Preferably, the substituent is not bulky, and is not alkyl or cycloalkyl group, but alkyl, cycloalkyl, haloalkyl, alkenyl group, alkynyl group, -Si(R 901 )(R 902 )(R 903 A group represented by -O-(R 904 A group represented by -S-(R 905 A group represented by -N(R 906 )(R 907 A group represented by ), an aralkyl group, -C(=O)R 801 The base represented by -COOR 802 It is more preferable that the group is not a halogen atom, a cyano group, or a nitro group.
[0517] In the organic EL element according to this embodiment, in the second compound represented by the general formula (2), R 201 ~R 208 Each of these independently consists of a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, or -Si(R 901 )(R 902 )(R 903 It is also preferable that the group be represented by ).
[0518] In the organic EL element according to this embodiment, in the second compound represented by the general formula (2), R 201 ~R 208 It is preferable that it be a hydrogen atom.
[0519] In the second compound, R 201 ~R 208 In the case of "substituted or unsubstituted" in the above, it is preferable that the substituents do not include the substituents that may increase bulk as described above, particularly substituted or unsubstituted alkyl groups and substituted or unsubstituted cycloalkyl groups. 201 ~R 208In the case of "substituted or unsubstituted" in this context, the substituents do not include substituted or unsubstituted alkyl groups and substituted or unsubstituted cycloalkyl groups. This prevents the suppression of intermolecular interactions caused by the presence of bulky substituents such as alkyl and cycloalkyl groups, thereby preventing a decrease in electron mobility. Furthermore, when such a second compound is used as the second light-emitting layer, it is possible to suppress a decrease in the recombination ability of holes and electrons in the first light-emitting layer, as well as a decrease in luminescence efficiency.
[0520] R is a substituent on the anthracene skeleton. 201 ~R 208 However, R is not a bulky substituent, but rather a substituent. 201 ~R 208 It is even more preferable that it is unsubstituted. Also, R, which is a substituent on the anthracene skeleton. 201 ~R 208 When R is not a bulky substituent, 201 ~R 208 When a substituent is attached to it, it is preferable that the substituent is not bulky, and R as a substituent 201 ~R 208 The substituent bonded to is preferably not an alkyl group or a cycloalkyl group, but rather an alkyl group, cycloalkyl group, haloalkyl group, alkenyl group, alkynyl group, -Si(R 901 )(R 902 )(R 903 A group represented by -O-(R 904 A group represented by -S-(R 905 A group represented by -N(R 906 )(R 907 A group represented by ), an aralkyl group, -C(=O)R 801 The base represented by -COOR 802 It is more preferable that the group is not a halogen atom, a cyano group, or a nitro group.
[0521] In both the first and second compounds, it is preferable that the groups described as "substituted or unsubstituted" are both "unsubstituted" groups.
[0522] In the organic EL element according to this embodiment, for example, Ar in the second compound represented by the general formula (2) 201 This is a substituted or unsubstituted dibenzofuranyl group.
[0523] In the organic EL element according to this embodiment, for example, Ar in the second compound represented by the general formula (2) 201 This is an unsubstituted dibenzofuranyl group.
[0524] In the organic EL element according to this embodiment, for example, the second compound represented by the general formula (2) contains at least one hydrogen atom, and at least one of the hydrogen atoms is deuterium.
[0525] In the organic EL element according to this embodiment, for example, L in the second compound represented by the general formula (2) 201 These are TEMP-63 or TEMP-68.
[0526] [ka]
[0527] In the general formulas (TEMP-63) to (TEMP-68) above, * represents a bond position.
[0528] In the organic EL element according to this embodiment, for example, Ar in the second compound represented by the general formula (2) 201 is a substituted or unsubstituted anthryl group, Benzoantryl group, Phenanthryl group, Benzophenanthryl group, Phenalenyl group, Pyrenyl group, Chrysenyl group, Benzocrisenyl group, Triphenylenyl group, Benzotriphenylenyl group, Tetraceryl group, Pentacenyl group, Fluoranthenyl group, Benzofluoranthenyl group, and It is at least one group selected from the group consisting of perilenyl groups.
[0529] In the organic EL element according to this embodiment, for example, Ar in the second compound represented by the general formula (2) 201 This is a substituted or unsubstituted fluorenyl group.
[0530] In the organic EL element according to this embodiment, for example, Ar in the second compound represented by the general formula (2) 201 This is a substituted or unsubstituted xanthenyl group.
[0531] In the organic EL element according to this embodiment, for example, Ar in the second compound represented by the general formula (2) 201 This is a benzoxanthenyl group.
[0532] (Method for producing the second compound) The second compound can be produced by known methods. Alternatively, the second compound can also be produced by following known methods and using known alternative reactions and starting materials tailored to the target product.
[0533] (Specific examples of the second compound) Specific examples of the second compound include, for example, the following compounds. However, the present invention is not limited to these specific examples of the second compound.
[0534] [ka]
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[0575] [ka]
[0576] [ka]
[0577] (The third compound and the fourth compound) The third and fourth compounds are each independently one or more compounds selected from the group consisting of compounds represented by the following general formula (3), compounds represented by the following general formula (4), compounds represented by the following general formula (5), compounds represented by the following general formula (6), compounds represented by the following general formula (7), compounds represented by the following general formula (8), compounds represented by the following general formula (9), and compounds represented by the following general formula (10).
[0578] (Compound represented by general formula (3)) This section describes compounds represented by general formula (3).
[0579] [ka]
[0580] (In the above general formula (3), R 301 ~R 310 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R 301 ~R 310 At least one of them is a monovalent group represented by the following general formula (31), R that does not form the aforementioned substituted or unsubstituted monoring, does not form the aforementioned substituted or unsubstituted fused ring, and is not a monovalent group represented by the following general formula (31) 301 ~R 310 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0581] [ka]
[0582] (In the above general formula (31), Ar 301 and Ar 302 Each of them operates independently. A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. L 301 ~L 303 Each of them operates independently. single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 30 carbon atoms, or A divalent heterocyclic group having 5 to 30 substituted or unsubstituted ring-forming atoms, * indicates the bond position in the pyrene ring in the general formula (3) above.
[0583] In the third and fourth compounds, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If multiple R 901They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another.
[0584] In the above general formula (3), R 301 ~R 310 Preferably, two of them are groups represented by the general formula (31).
[0585] In one embodiment, the compound represented by general formula (3) is the compound represented by the following general formula (33).
[0586] [ka]
[0587] (In the above general formula (33), R 311 ~R 318 Each of these independently represents R, which is not a monovalent group represented by general formula (31) in general formula (3). 301 ~R 310 It is synonymous with, L 311 ~L 316 Each of them operates independently. single bond, A substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 30 ring-forming atoms, which is substituted or unsubstituted, Ar 312 、Ar 313 、Ar 315 and Ar 316 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. )
[0588] In the general formula (31), L 301 is preferably a single bond, and L 302 and L 303 are preferably single bonds.
[0589] In one embodiment, the compound represented by the general formula (3) is represented by the following general formula (34) or general formula (35).
[0590]
Chemical formula
[0591] (In the general formula (34), R 311 ~R 318 are each independently the same as R 301 ~R 310 in the general formula (3), which is not the monovalent group represented by the general formula (31), L 312 、L 313 、L 315 and L 316 are each independently the same as L 312 、L 313 、L 315 and L 316 in the general formula (33), Ar 312 、Ar 313 、Ar 315 and Ar 316Each of these independently corresponds to Ar in the general formula (33) 312 Ar 313 Ar 315 and Ar 316 (This is synonymous with...)
[0592] [ka]
[0593] (In the above general formula (35), R 311 ~R 318 Each of these independently represents R, which is not a monovalent group represented by general formula (31) in general formula (3). 301 ~R 310 It is synonymous with, Ar 312 Ar 313 Ar 315 and Ar 316 Each of these independently corresponds to Ar in the general formula (33) 312 Ar 313 Ar 315 and Ar 316 (This is synonymous with...)
[0594] In the above general formula (31), preferably, Ar 301 and Ar 302 At least one of these is a group represented by the following general formula (36). In the above general formulas (33) to (35), preferably, Ar 312 and Ar 313 At least one of these is a group represented by the following general formula (36). In the above general formulas (33) to (35), preferably, Ar 315 and Ar 316 At least one of these is a group represented by the following general formula (36).
[0595] [ka]
[0596] (In the above general formula (36), X3 represents an oxygen atom or a sulfur atom. R 321 ~R 327 Of these, one or more pairs consisting of two or more adjacent items, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 321 ~R 327 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. * is L 302 , L 303 , L 312 , L 313 , L 315 or L 316 (This indicates the bonding position.)
[0597] X3 is preferably an oxygen atom.
[0598] R 321 ~R 327 At least one of them is Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is preferable that the heterocyclic group has 5 to 50 substituted or unsubstituted ring-forming atoms.
[0599] In the above general formula (31), Ar 301 The group is represented by the general formula (36), and Ar 302 It is preferable that the group is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms. In the above general formulas (33) to (35), Ar 312 The group is represented by the general formula (36), and Ar 313 It is preferable that the group is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms. In the above general formulas (33) to (35), Ar 315 The group is represented by the general formula (36), and Ar 316 It is preferable that the group is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.
[0600] In one embodiment, the compound represented by general formula (3) is represented by the following general formula (37).
[0601] [ka]
[0602] (In the above general formula (37), R 311 ~R318 is, independently of each other, R which is not a monovalent group represented by the general formula (31) in the general formula (3) 301 ~R 310 has the same meaning as, R 321 ~R 327 and one or more sets of combinations of two or more adjacent ones among are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or do not bond to each other, R 341 ~R 347 and one or more sets of combinations of two or more adjacent ones among are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or do not bond to each other, do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring, R 321 ~R 327 and R 341 ~R 347 are, independently of each other, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by -O-(R 904 ) group represented by -S-(R 905 ) group represented by -N(R 906 )(R 907 ) group represented by a halogen atom, a cyano group, a nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 331 ~R 335 R 351 ~R 355 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0603] Examples of compounds represented by the general formula (3) include the following compounds.
[0604] [ka]
[0605] [ka]
[0606] [ka]
[0607] [ka]
[0608] [ka]
[0609] (Compounds represented by general formula (4)) This section describes compounds represented by general formula (4).
[0610] [ka]
[0611] (In the above general formula (4), Z is independently either a CRa or a nitrogen atom. Rings A1 and A2 are independent of each other. A substituted or unsubstituted ring-forming aromatic hydrocarbon ring with 6 to 50 carbon atoms, or These are heterocycles with 5 to 50 ring-forming atoms, either substituted or unsubstituted. If there are multiple Ras, then one or more pairs of adjacent Ras are... They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, n21 and n22 are independently 0, 1, 2, 3, or 4. If there are multiple Rb groups, then one or more pairs of adjacent Rb groups are... They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, If there are multiple Rc, then one or more pairs of adjacent Rc elements are: They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, Ra, Rb, and Rc, which do not form the aforementioned substituted or unsubstituted monorings and do not form the aforementioned substituted or unsubstituted fused rings, are each independently: Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0612] The "aromatic hydrocarbon rings" of the A1 and A2 rings have the same structure as the compounds in which a hydrogen atom is introduced to the "aryl group" mentioned above. The "aromatic hydrocarbon rings" of rings A1 and A2 include two carbon atoms on the central condensed biring structure of general formula (4) as ring-forming atoms. Specific examples of "substituted or unsubstituted ring-forming aromatic hydrocarbon rings with 6 to 50 carbon atoms" include compounds in which a hydrogen atom has been introduced to the "aryl group" described in specific example group G1.
[0613] The heterocyclic rings of the A1 and A2 rings have the same structure as compounds in which a hydrogen atom is introduced into the heterocyclic group described above. The "heterocyclic rings" of the A1 and A2 rings include two carbon atoms on the central fused bicyclic ring structure of the general formula (4) as ring-forming atoms. Specific examples of "heterocyclic rings with 5 to 50 substituted or unsubstituted ring-forming atoms" include compounds in which hydrogen atoms have been introduced into the "heterocyclic group" described in specific example group G2.
[0614] Rb is bonded to either one of the carbon atoms forming an aromatic hydrocarbon ring as an A1 ring, or to any of the atoms forming a heterocycle as an A1 ring.
[0615] Rc is bonded to either one of the carbon atoms forming an aromatic hydrocarbon ring as an A2 ring, or to any of the atoms forming a heterocycle as an A2 ring.
[0616] It is preferable that at least one of Ra, Rb, and Rc is a group represented by the following general formula (4a), and it is more preferable that at least two are groups represented by the following general formula (4a).
[0617] [ka]
[0618] (In the above general formula (4a), L 401 teeth, single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 30 carbon atoms, or A divalent heterocyclic group having 5 to 30 substituted or unsubstituted ring-forming atoms, Ar 401 teeth, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, or It is a group represented by the following general formula (4b).
[0619] [ka]
[0620] (In the above general formula (4b), L 402 and L 403 Each of them operates independently. single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 30 carbon atoms, or A divalent heterocyclic group having 5 to 30 substituted or unsubstituted ring-forming atoms, Ar 402 and Ar 403 The group consisting of is They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, Ar that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 402 and Ar 403 Each of them operates independently. A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0621] In one embodiment, the compound represented by the general formula (4) is represented by the following general formula (42).
[0622] [ka]
[0623] (In the above general formula (42), R 401 ~R 411 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 401 ~R 411 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0624] R 401 ~R 411 Preferably, at least one of these groups is a group represented by the general formula (4a), and more preferably, at least two groups are represented by the general formula (4a). R 404 and R 411 It is preferable that the group is represented by the general formula (4a).
[0625] In one embodiment, the compound represented by general formula (4) is a compound in which a structure represented by the following general formula (4-1) or general formula (4-2) is bonded to the A1 ring. In one embodiment, the compound represented by the general formula (42) is R404 ~R 407 This compound has a ring to which a structure represented by the following general formula (4-1) or general formula (4-2) is attached.
[0626] [ka]
[0627] (In the general formula (4-1) above, the two *s are each independently bonded to a ring-forming carbon atom of an aromatic hydrocarbon ring as the A1 ring of the general formula (4) or to a ring-forming atom of a heterocycle, or to the R of the general formula (42) above. 404 ~R 407 Combine with any of the following: The three * in general formula (4-2) are each independently bonded to a ring-forming carbon atom of an aromatic hydrocarbon ring as the A1 ring in general formula (4) or to a ring-forming atom of a heterocycle, or to the R in general formula (42) 404 ~R 407 Combine with any of the following: R 421 ~R 427 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R 431 ~R 438 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 421 ~R 427 R 431 ~R 438 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0628] In one embodiment, the compound represented by general formula (4) is a compound represented by the following general formulas (41-3), (41-4), or (41-5).
[0629] [ka]
[0630] [ka]
[0631] [ka]
[0632] (In the above general formulas (41-3), (41-4), and (41-5), The A1 ring is defined as shown in the general formula (4) above, R 421 ~R427 Each of these independently corresponds to R in the general formula (4-1) above. 421 ~R 427 It is synonymous with, R 440 ~R 448 Each of these independently corresponds to R in the general formula (42) above. 401 ~R 411 (This is synonymous with...)
[0633] In one embodiment, the substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms as the A1 ring of the general formula (41-5) is A substituted or unsubstituted naphthalene ring, It is a substituted or unsubstituted fluorene ring.
[0634] In one embodiment, the heterocycle of the general formula (41-5) having 5 to 50 substituted or unsubstituted ring-forming atoms as the A1 ring is, Substituted or unsubstituted dibenzofuran rings, A substituted or unsubstituted carbazole ring, It is a substituted or unsubstituted dibenzothiophene ring.
[0635] In one embodiment, the compound represented by general formula (4) or general formula (42) is selected from the group consisting of compounds represented by the following general formulas (461) to (467).
[0636] [ka]
[0637] [ka]
[0638] [ka]
[0639] [ka]
[0640] [ka]
[0641] (Among the above general formulas (461), (462), (463), (464), (465), (466), and (467), R 421 ~R 427 Each of these independently corresponds to R in the general formula (4-1) above. 421 ~R 427 It is synonymous with, R 431 ~R 438 Each of these independently corresponds to R in the general formula (4-2) above. 431 ~R 438 It is synonymous with, R 440 ~R 448 R 451 ~R 454 Each of these independently corresponds to R in the general formula (42) above. 401 ~R 411 It is synonymous with, X4 is an oxygen atom, NR 801 , or C(R 802 )(R 803 ) and R 801 , R 802 and R 803 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, R801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 They are either identical or different from one another. R 803 If multiple R 803 They are either identical or different to one another.
[0642] In one embodiment, the compound represented by the general formula (42) is R 401 ~R 411 One or more pairs of adjacent elements from among these elements bond to each other to form a substituted or unsubstituted monoring, or bond to each other to form a substituted or unsubstituted fused ring, and this embodiment will be described in detail below as a compound represented by general formula (45).
[0643] (Compound represented by general formula (45)) This section describes compounds represented by general formula (45).
[0644] [ka]
[0645] (In the above general formula (45), R 461 and R 462 A set consisting of and, R 462 and R 463 A set consisting of and, R 464 and R 465 A set consisting of and, R 465 and R 466 A set consisting of and, R 466 and R 467 A set consisting of and, R 468 and R 469 A set consisting of and, R 469 and R 470 A set consisting of and, R 470 and R 471Two or more pairs selected from the group consisting of and combine to form a substituted or unsubstituted monoring or a substituted or unsubstituted fused ring. however, R 461 and R 462 A set consisting of and R 462 and R 463 A set consisting of and; R 464 and R 465 A set consisting of and R 465 and R 466 A set consisting of and; R 465 and R 466 A set consisting of and R 466 and R 467 A set consisting of and; R 468 and R 469 A set consisting of and R 469 and R 470 A set consisting of and; and R 469 and R 470 A set consisting of and R 470 and R 471 A pair consisting of and cannot simultaneously form a ring. R 461 ~R 471 The two or more rings formed by are either identical or different from each other. R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 461 ~R 471 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R905 ), -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0646] In the above general formula (45), R n and R n+1 (where n represents an integer chosen from 461, 462, 464-466, and 468-470) are combined into R n and R n+1 Together with the two ring-forming carbon atoms to which it is bonded, it forms a substituted or unsubstituted monoring or a substituted or unsubstituted fused ring. The ring is preferably composed of atoms selected from the group consisting of carbon atoms, oxygen atoms, sulfur atoms, and nitrogen atoms, and the number of atoms in the ring is preferably 3 to 7, more preferably 5 or 6.
[0647] The number of ring structures in the compound represented by the general formula (45) is, for example, two, three, or four. Two or more ring structures may each be located on the same benzene ring on the parent skeleton of the general formula (45), or they may be located on different benzene rings. For example, if there are three ring structures, one ring structure may be located on each of the three benzene rings of the general formula (45).
[0648] Examples of the above-mentioned ring structure in the compound represented by the general formula (45) include the structures represented by the following general formulas (451) to (460).
[0649] [ka]
[0650] (In the above general formulas (451) to (457), *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14 are each R n and R n+1 This represents the two ring-forming carbon atoms to which it is bonded. R n The ring-forming carbon atoms to which are bonded may be either of the two ring-forming carbon atoms represented by *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14. X 45 C(R 4512 )(R 4513 ), NR 4514 , an oxygen atom or a sulfur atom, R 4501 ~R 4506 and R 4512 ~R 4513 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 4501 ~R 4514 Each of these independently corresponds to R in the general formula (45) above. 461 ~R 471 (This is synonymous with...)
[0651] [ka]
[0652] (In the above general formulas (458) to (460), *1 and *2, and *3 and *4 respectively, are R n and R n+1 This represents the two ring-forming carbon atoms to which it is bonded. R n The ring-forming carbon atoms to which it is bonded may be either the two ring-forming carbon atoms represented by *1 and *2, or *3 and *4. X 45C(R 4512 )(R 4513 ), NR 4514 , an oxygen atom or a sulfur atom, R 4512 ~R 4513 and R 4515 ~R 4525 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 4512 ~R 4513 , R 4515 ~R 4521 and R 4522 ~R 4525 , and R 4514 Each of these independently corresponds to R in the general formula (45) above. 461 ~R 471 (This is synonymous with...)
[0653] In the above general formula (45), R 462 , R 464 , R 465 , R 470 and R 471 at least one of (preferably R 462 , R 465 and R 470 At least one of, more preferably R 462 Preferably, the group is one that does not form a ring structure.
[0654] (i) In the above general formula (45), R n and R n+1 The substituent when the ring structure formed by has substituents, (ii) In the general formula (45) above, R that does not form a ring structure 461 ~R 471 , and (iii) R in equations (451) to (460) 4501 ~R 4514 , R 4515 ~R4525 Preferably, each independently, hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, or It is one of the groups selected from the group consisting of groups represented by the following general formulas (461) to (464).
[0655] [ka]
[0656] (In the above general formulas (461) to (464), R d Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. X 46 C(R 801 )(R 802 ), NR 803 , an oxygen atom or a sulfur atom, R 801 , R 802 and R 803 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, R 801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 They are either identical or different from one another. R 803 If multiple R 803 They are either identical or different from one another. p1 is 5, p2 is 4, p3 is 3, p4 is 7, In the general formulas (461) to (464) above, the asterisks (*) independently indicate the bonding position with the ring structure. In the third and fourth compounds, R 901 ~R 907 This is defined as described above.
[0657] In one embodiment, the compound represented by the general formula (45) is represented by any of the following general formulas (45-1) to (45-6).
[0658] [ka]
[0659] [ka]
[0660] (In the above general formulas (45-1) to (45-6), Rings d~i are, independently, substituted or unsubstituted monorings or substituted or unsubstituted fused rings. R 461 ~R 471 Each of these independently corresponds to R in the general formula (45) above. 461 ~R 471 (This is synonymous with...)
[0661] In one embodiment, the compound represented by the general formula (45) is represented by any of the following general formulas (45-7) to (45-12).
[0662] [ka]
[0663] [ka]
[0664] (In the above general formulas (45-7) to (45-12), Rings d~f, k, and j are, independently, substituted or unsubstituted monorings or substituted or unsubstituted fused rings. R 461 ~R 471 Each of these independently corresponds to R in the general formula (45) above. 461 ~R 471 (This is synonymous with...)
[0665] In one embodiment, the compound represented by the general formula (45) is represented by any of the following general formulas (45-13) to (45-21).
[0666] [ka]
[0667] [ka]
[0668] [ka]
[0669] (In the above general formulas (45-13) to (45-21), Each of the rings d~k is independently a substituted or unsubstituted monoring or a substituted or unsubstituted fused ring. R 461 ~R 471 Each of these independently corresponds to R in the general formula (45) above. 461 ~R 471 (This is synonymous with...)
[0670] Examples of substituents when the ring g or ring h further has substituents include: Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, The base represented by the general formula (461) above, The group represented by the general formula (463) above, or Examples include the group represented by the general formula (464) mentioned above.
[0671] In one embodiment, the compound represented by the general formula (45) is represented by any of the following general formulas (45-22) to (45-25).
[0672] [ka]
[0673] (In the above general formulas (45-22) to (45-25), X 46 and X 47 Each of them independently, C(R 801 )(R 802 ), NR 803 , an oxygen atom or a sulfur atom, R 461 ~R 471 R 481 ~R 488 Each of these independently corresponds to R in the general formula (45) above. 461 ~R 471 It is synonymous with [the above]. R 801 , R 802 and R 803 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, R 801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 They are either identical or different from one another. R 803 If multiple R 803 They are either identical or different to one another.
[0674] In one embodiment, the compound represented by the general formula (45) is represented by the following general formula (45-26).
[0675] [ka]
[0676] (In the above general formula (45-26), X 46 C(R 801 )(R 802 ), NR 803 , an oxygen atom or a sulfur atom, R 463 , R 464 , R 467 , R 468 , R 471 , and R 481 ~R 492 Each of these independently corresponds to R in the general formula (45) above. 461 ~R 471 It is synonymous with [the above]. R 801 , R 802 and R 803 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, R 801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 They are either identical or different from one another. R 803 If multiple R 803 They are either identical or different to one another.
[0677] Examples of compounds represented by the general formula (4) include the following compounds. In the examples below, Ph represents a phenyl group and D represents a deuterium atom.
[0678] [ka]
[0679] [ka]
[0680] [ka]
[0681] [ka]
[0682] [ka]
[0683] [ka]
[0684] [ka]
[0685] [ka]
[0686] [ka]
[0687] [ka]
[0688] (Compound represented by general formula (5)) This section describes the compound represented by general formula (5). The compound represented by general formula (5) is the same compound as the compound represented by general formula (41-3) mentioned above.
[0689] [ka]
[0690] (In the above general formula (5), R 501 ~R 507 and R 511 ~R 517 Of these, one or more pairs consisting of two or more adjacent items, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 501 ~R 507 and R 511 ~R 517 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 521 and R 522 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0691] "R 501 ~R 507 and R 511 ~R 517 "A set of two or more adjacent elements" is, for example, R 501 and R 502 A group consisting of R 502 and R 503 A group consisting of R 503 and R 504 A group consisting of R 505 and R 506 A group consisting of R506 and R 507 A group consisting of R 501 and R 502 and R 503 This is a combination of sets and other elements.
[0692] In one embodiment, R 501 ~R 507 and R 511 ~R 517 At least one, preferably two, of are -N(R 906 )(R 907 It is a base represented by ).
[0693] In one embodiment, R 501 ~R 507 and R 511 ~R 517 Each of them operates independently. hydrogen atom, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms.
[0694] In one embodiment, the compound represented by the general formula (5) is the compound represented by the following general formula (52).
[0695] [ka]
[0696] (In the above general formula (52), R 531 ~R 534 and R 541 ~R 544 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 531 ~R534 , R 541 ~R 544 , and R 551 and R 552 Each of them operates independently. hydrogen atom, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 561 ~R 564 Each of them operates independently. A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0697] In one embodiment, the compound represented by the general formula (5) is the compound represented by the following general formula (53).
[0698] [ka]
[0699] (In the above general formula (53), R 551 , R 552 and R 561 ~R 564 Each of these independently corresponds to R in the general formula (52) above. 551 , R 552 and R 561 ~R 564 (This is synonymous with...)
[0700] In one embodiment, R in the general formulas (52) and (53) 561 ~R 564 Each of these is independently a substituted or unsubstituted ring-forming aryl group (preferably a phenyl group) having 6 to 50 carbon atoms.
[0701] In one embodiment, R in the general formula (5) 521 and R 522 , R in the above general formulas (52) and (53) 551 and R552 This is a hydrogen atom.
[0702] In one embodiment, the substituents in the general formulas (5), (52), and (53) when referring to "substituted or unsubstituted" are: Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms.
[0703] Examples of compounds represented by the general formula (5) include the following compounds.
[0704] [ka]
[0705] [ka]
[0706] [ka]
[0707] [ka]
[0708] [ka]
[0709] [ka]
[0710]
change
[0711]
change
[0712]
change
[0713]
change
[0714]
change
[0715]
change
[0716]
change
[0717]
change
[0718]
change
[0719]
change
[0720] [ka]
[0721] (Compounds represented by general formula (6)) This section describes compounds represented by general formula (6).
[0722] [ka]
[0723] (In the above general formula (6), Rings a, b, and c are each independent of the others. A substituted or unsubstituted ring-forming aromatic hydrocarbon ring with 6 to 50 carbon atoms, or These are heterocycles with 5 to 50 ring-forming atoms, either substituted or unsubstituted. R 601 and R 602 Each of these rings independently bonds with the a, b, or c ring to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R that does not form the aforementioned substituted or unsubstituted heteroalgebra 601 and R 602 Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0724] Rings a, b, and c are rings that condense into the central condensed biring structure of general formula (6) consisting of a boron atom and two nitrogen atoms (substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 ring-forming carbon atoms, or substituted or unsubstituted heterocycles with 5 to 50 ring-forming atoms).
[0725] The aromatic hydrocarbon rings of rings a, b, and c have the same structure as the compounds in which a hydrogen atom is introduced to the aforementioned aryl group. The "aromatic hydrocarbon ring" of ring a includes three carbon atoms on the central condensed biring structure of general formula (6) as ring-forming atoms. The "aromatic hydrocarbon rings" of rings b and c include two carbon atoms on the central condensed two-ring structure of general formula (6) as ring-forming atoms.
[0726] Specific examples of "substituted or unsubstituted ring-forming aromatic hydrocarbon rings with 6 to 50 carbon atoms" include compounds in which a hydrogen atom has been introduced to the "aryl group" described in specific example group G1. The heterocyclic rings of the a, b, and c rings have the same structure as compounds in which a hydrogen atom is introduced into the heterocyclic group described above. The heterocycle of ring a includes three carbon atoms on the central fused biring structure of general formula (6) as ring-forming atoms. The heterocycles of rings b and c include two carbon atoms on the central fused biring structure of general formula (6) as ring-forming atoms. Specific examples of "heterocycles with 5 to 50 substituted or unsubstituted ring-forming atoms" include compounds in which hydrogen atoms are introduced into the "heterocycle group" described in specific example group G2.
[0727] R 601 and R 602 Each of these may independently bond with a ring a, a ring b, or a ring c to form a substituted or unsubstituted heterocycle. In this case, the heterocycle contains a nitrogen atom on the central fused biring structure of general formula (6). In this case, the heterocycle may also contain heteroatoms other than nitrogen. 601 and R 602 Specifically, when it is said that it bonds with ring a, ring b, or ring c, it means that it bonds with an atom constituting ring a, ring b, or ring c and R 601 and R 602 This means that the atoms that make up the compound are bonded together. For example, R 601 It binds to the a ring, R 601A nitrogen-containing heterocycle of two-ring condensation (or three-ring condensation or more) may be formed by the condensation of a ring containing a nitrogen ring with an a-ring. Specific examples of such nitrogen-containing heterocycles include compounds from specific example group G2 that correspond to two-ring condensation or more heterocyclic groups containing nitrogen. R 601 When it bonds with the b ring, R 602 When it bonds with the a ring, and R 602 The same applies when it is bonded to a c-ring.
[0728] In one embodiment, the a-ring, b-ring, and c-ring in the general formula (6) are each independently substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 ring-forming carbon atoms. In one embodiment, the a-ring, b-ring, and c-ring in the general formula (6) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.
[0729] In one embodiment, R in the general formula (6) 601 and R 602 Each of them operates independently. A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. Preferably, it is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms that forms a ring.
[0730] In one embodiment, the compound represented by the general formula (6) is the compound represented by the following general formula (62).
[0731] [ka]
[0732] (In the above general formula (62), R 601A R 611 and R 621 It combines with one or more elements selected from the group consisting of to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R602A R 613 and R 614 It combines with one or more elements selected from the group consisting of to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R that does not form the aforementioned substituted or unsubstituted heteroalgebra 601A and R 602A Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 611 ~R 621 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted heterocycle, does not form the aforementioned substituted or unsubstituted monocycle, and does not form the aforementioned substituted or unsubstituted fused ring. 611 ~R 621 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0733] R in the above general formula (62) 601A and R 602A These are, respectively, R in the general formula (6) above. 601 and R 602 It is the corresponding base. For example, R 601A and R 611 These may bond to form a two-ring condensation (or three-ring condensation or more) nitrogen-containing heterocycle in which the ring containing these and the benzene ring corresponding to the a-ring are fused. Specific examples of such nitrogen-containing heterocycles include compounds from specific example group G2 that correspond to two-ring condensation or more heterocycle groups containing nitrogen. 601A and R 621 When they are joined, R 602A and R 613 When they are joined, and R 602A and R 614 The same applies when they are joined together.
[0734] R 611 ~R 621 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a substituted or unsubstituted monoring, or They may bond to each other to form substituted or unsubstituted fused rings. For example, R 611 and R 612These rings may bond together to form a structure in which a benzene ring, indole ring, pyrrole ring, benzofuran ring, or benzothiophene ring is fused to the six-membered ring to which they are bonded. The resulting fused ring may be a naphthalene ring, carbazole ring, indole ring, dibenzofuran ring, or dibenzothiophene ring.
[0735] In one embodiment, R does not contribute to ring formation. 611 ~R 621 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms.
[0736] In one embodiment, R does not contribute to ring formation. 611 ~R 621 Each of them operates independently. hydrogen atom, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms.
[0737] In one embodiment, R does not contribute to ring formation. 611 ~R 621 Each of them operates independently. Hydrogen atom, or These are substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms.
[0738] In one embodiment, R does not contribute to ring formation. 611 ~R 621 Each of them operates independently. Hydrogen atom, or A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, R 611 ~R 621 At least one of these is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[0739] In one embodiment, the compound represented by the general formula (62) is the compound represented by the following general formula (63).
[0740] [ka]
[0741] (In the above general formula (63), R 631 R 646 It combines with to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R 633 R 647 It combines with to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R 634 R 651 It combines with to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R 641 R 642 It combines with to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R 631 ~R 651 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted heterocycle, does not form the aforementioned substituted or unsubstituted monocycle, and does not form the aforementioned substituted or unsubstituted fused ring. 631 ~R 651 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0742] R 631 R 646 It may be combined with to form a substituted or unsubstituted heterocyclic ring. For example, R 631 and R 646 They combine, R 646 A nitrogen-containing heterocycle of three or more rings may be formed by the condensation of a benzene ring to which the nitrogen is bonded, a ring containing nitrogen, and a benzene ring corresponding to the a-ring. Specific examples of such nitrogen-containing heterocycles include compounds from specific example group G2 that correspond to three or more heterocyclic groups containing nitrogen. 633 and R 647 When they are joined, R 634 and R 651 When they are joined, and R 641 and R 642 The same applies when they are joined together.
[0743] In one embodiment, R does not contribute to ring formation. 631 ~R 651 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms.
[0744] In one embodiment, R does not contribute to ring formation. 631 ~R 651 Each of them operates independently. hydrogen atom, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms.
[0745] In one embodiment, R does not contribute to ring formation. 631 ~R 651 Each of them operates independently. Hydrogen atom, or These are substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms.
[0746] In one embodiment, R does not contribute to ring formation. 631 ~R 651 Each of them operates independently. Hydrogen atom, or A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, R 631 ~R 651 At least one of these is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[0747] In one embodiment, the compound represented by the general formula (63) is the compound represented by the following general formula (63A).
[0748] [ka]
[0749] (In the above general formula (63A), R 661 teeth, hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, R 662 ~R 665 Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, (These are substituted or unsubstituted aryl groups with 6 to 50 carbon atoms forming a ring.)
[0750] In one embodiment, R 661 ~R 665 Each of them operates independently. A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, These are substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms.
[0751] In one embodiment, R 661 ~R 665 Each of these is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[0752] In one embodiment, the compound represented by the general formula (63) is the compound represented by the following general formula (63B).
[0753] [ka]
[0754] (In the above general formula (63B), R 671 and R 672 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -N(R 906 )(R 907 A base represented by ) or A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, R 673 ~R 675 Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -N(R 906 )(R 907 A base represented by ) or (These are substituted or unsubstituted aryl groups with 6 to 50 carbon atoms forming a ring.)
[0755] In one embodiment, the compound represented by the general formula (63) is the compound represented by the following general formula (63B').
[0756] [ka]
[0757] (In the above general formula (63B'), R 672 ~R 675 Each of these independently corresponds to R in the general formula (63B) 672 ~R 675 (This is synonymous with...)
[0758] In one embodiment, R 671 ~R 675 At least one of them is Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -N(R 906 )(R 907 A base represented by ) or These are substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms.
[0759] In one embodiment, R 672 teeth, hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, -N(R 906 )(R 907 A base represented by ) or A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, R 671 and R 673 ~R 675 Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, -N(R 906 )(R 907 A base represented by ) or These are substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms.
[0760] In one embodiment, the compound represented by the general formula (63) is the compound represented by the following general formula (63C).
[0761] [ka]
[0762] (In the above general formula (63C), R 681 and R 682 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, These are substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms. R 683 ~R 686 Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, (These are substituted or unsubstituted aryl groups with 6 to 50 carbon atoms forming a ring.)
[0763] In one embodiment, the compound represented by the general formula (63) is the compound represented by the following general formula (63C').
[0764] [ka]
[0765] (In the above general formula (63C'), R 683 ~R 686 Each of these independently corresponds to R in the general formula (63C) 683 ~R 686 (This is synonymous with...)
[0766] In one embodiment, R 681 ~R 686 Each of them operates independently. A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, These are substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms.
[0767] In one embodiment, R 681 ~R 686 These are, independently, substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms.
[0768] The compound represented by the general formula (6) is first formed by linking the a-ring, b-ring, and c-ring with a linking group (NR 601 Groups including NR 602 An intermediate can be produced by bonding the rings with a group containing a boron atom (first reaction), and the final product can be produced by bonding the a, b, and c rings with a linking group (a group containing a boron atom) (second reaction). In the first reaction, amination reactions such as the Bachbrutt-Hartwig reaction can be applied. In the second reaction, tandem hetero-Friedel-Crafts reactions can be applied.
[0769] The following are specific examples of compounds represented by the general formula (6), but these are merely examples, and the compounds represented by the general formula (6) are not limited to the following examples.
[0770] [ka]
[0771] [ka]
[0772] [ka]
[0773] [ka]
[0774] [ka]
[0775] [ka]
[0776] [ka]
[0777] [ka]
[0778] [ka]
[0779] [ka]
[0780] [ka]
[0781] [ka]
[0782] (Compounds represented by general formula (7)) The compound represented by general formula (7) will be explained.
[0783] [ka]
[0784] [ka]
[0785] (In the above general formula (7), The r-ring is a ring represented by general formula (72) or general formula (73) that condenses at any position of the adjacent ring, The q-ring and the s-ring are rings represented by the general formula (74) that condense independently at any position of the adjacent ring, The p-ring and t-ring each independently condense at any position on the adjacent ring, and the structure is represented by the general formula (75) or general formula (76). X7 is an oxygen atom, a sulfur atom, or NR 702 That is the case. R 701 If multiple Rs exist, then multiple adjacent Rs 701 teeth, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 701 and R 702 Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. Ar 701 and Ar 702 Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. L 701 teeth, Substituted or unsubstituted alkylene groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenylene groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkylylene groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkylene groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, m1 is 0, 1, or 2. m2 is 0, 1, 2, 3, or 4. m3 is independently 0, 1, 2, or 3. m4 is independently 0, 1, 2, 3, 4, or 5. R 701 If multiple R 701 They are either identical or different from each other. If multiple X7s exist, they may be identical or different from one another. R 702 If multiple R 702 They are either identical or different from each other. Ar 701 If multiple Ar 701 They are either identical or different from each other. Ar 702 If multiple Ar 702 They are either identical or different from each other. L 701 If there are multiple L 701 They are either identical or different to one another.
[0786] In the general formula (7) above, the p, q, r, s, and t rings are condensed with adjacent rings by sharing two carbon atoms. The position and orientation of the condensation are not limited, and condensation is possible at any position and orientation.
[0787] In one embodiment, in the general formula (72) or general formula (73) as the r-ring, m1=0 or m2=0.
[0788] In one embodiment, the compound represented by general formula (7) is represented by any of the following general formulas (71-1) to (71-6).
[0789] [ka]
[0790] [ka]
[0791] [ka]
[0792] [ka]
[0793] [ka]
[0794] [ka]
[0795] (In the above general formulas (71-1) to (71-6), R 701 X7, Ar 701 Ar 702 , L 701m1 and m3 are, respectively, R in the general formula (7) above. 701 X7, Ar 701 Ar 702 , L 701 (This is synonymous with m1 and m3.)
[0796] In one embodiment, the compound represented by general formula (7) is represented by any of the following general formulas (71-11) to (71-13).
[0797] [ka]
[0798] [ka]
[0799] [ka]
[0800] (In the above general formulas (71-11) to (71-13), R 701 X7, Ar 701 Ar 702 , L 701 m1, m3, and m4 are, respectively, R in the general formula (7) above. 701 X7, Ar 701 Ar 702 , L 701 (This is synonymous with m1, m3, and m4.)
[0801] In one embodiment, the compound represented by general formula (7) is represented by any of the following general formulas (71-21) to (71-25).
[0802] [ka]
[0803] [ka]
[0804] [ka]
[0805] [ka]
[0806] [ka]
[0807] (In the above general formulas (71-21) to (71-25), R 701 X7, Ar 701 Ar 702 , L 701 m1 and m4 are, respectively, R in the general formula (7) above. 701 X7, Ar 701 Ar 702 , L 701 (This is synonymous with m1 and m4.)
[0808] In one embodiment, the compound represented by general formula (7) is represented by any of the following general formulas (71-31) to (71-33).
[0809] [ka]
[0810] [ka]
[0811] [ka]
[0812] (In the above general formulas (71-31) to (71-33), R 701X7, Ar 701 Ar 702 , L 701 m2 to m4 are, respectively, R in the general formula (7) above. 701 X7, Ar 701 Ar 702 , L 701 (This is synonymous with m2~m4.)
[0813] In one embodiment, Ar 701 and Ar 702 However, each of these is independently a substituted or unsubstituted aryl group with 6 to 50 carbon atoms forming a ring.
[0814] In one embodiment, Ar 701 and Ar 702 One of them is a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, Ar 701 and Ar 702 The other side is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0815] Examples of compounds represented by the general formula (7) include the following compounds.
[0816] [ka]
[0817] [ka]
[0818] [ka]
[0819] [ka]
[0820] [ka]
[0821] [ka]
[0822] (Compounds represented by general formula (8)) This section describes compounds represented by general formula (8).
[0823] [ka]
[0824] (In the above general formula (8), R 801 and R 802 , R 802 and R 803 , and R 803 and R 804 At least one pair of these combines with each other to form a divalent group represented by the following general formula (82): R 805 and R 806 , R 806 and R 807 , and R 807 and R 808 At least one pair of these groups combines with each other to form a divalent group represented by the following general formula (83).
[0825] [ka]
[0826] (R that does not form a divalent group as shown in the general formula (82) above) 801 ~R 804 , and R 811 ~R 814 At least one of them is a monovalent group represented by the following general formula (84): R that does not form a divalent group as shown in the general formula (83) above 805 ~R 808 , and R 821 ~R 824At least one of them is a monovalent group represented by the following general formula (84): X8 is an oxygen atom, a sulfur atom, or NR 809 And, R that does not form a divalent group represented by the general formulas (82) and (83) and is not a monovalent group represented by the general formula (84) 801 ~R 808 , R which is not a monovalent group represented by the general formula (84) 811 ~R 814 and R 821 ~R 824 , and R 809 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0827] [ka]
[0828] (In the above general formula (84), Ar 801 and Ar 802Each of them operates independently. A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. L 801 ~L 803 Each of them operates independently. single bond, Substituted or unsubstituted ring-forming arylene groups with 6 to 30 carbon atoms, A substituted or unsubstituted divalent heterocyclic group with 5 to 30 ring-forming atoms, or A divalent linking group is formed by the bonding of 2 to 4 groups selected from the group consisting of substituted or unsubstituted ring-forming arylene groups with 6 to 30 carbon atoms and substituted or unsubstituted divalent heterocyclic groups with 5 to 30 ring-forming atoms. In the general formula (84), the asterisk (*) indicates the bonding position with the ring structure represented by general formula (8), or the group represented by general formula (82) or general formula (83).
[0829] In the general formula (8) above, the positions in which the divalent group represented by general formula (82) and the divalent group represented by general formula (83) are formed are not particularly limited, R 801 ~R 808 The group can be formed at any possible location.
[0830] In one embodiment, the compound represented by general formula (8) is represented by any of the following general formulas (81-1) to (81-6).
[0831] [ka]
[0832] [ka]
[0833] [ka]
[0834] (In the general formulas (81-1) to (81-6), X8 has the same meaning as X8 in the general formula (8), R 801 ~R 824 at least two of them are monovalent groups represented by the general formula (84), R that is not a monovalent group represented by the general formula (84) 801 ~R 824 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by, -O-(R 904 ) group represented by, -S-(R 905 ) group represented by, -N(R 906 )(R 907 ) group represented by, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.)
[0835] In one embodiment, the compound represented by the general formula (8) is represented by any one of the following general formulas (81-7) to (81-18).
[0836]
Chemical formula
[0837]
Chemical formula
[0838] [ka]
[0839] [ka]
[0840] [ka]
[0841] [ka]
[0842] (In the above general formulas (81-7) to (81-18), X8 is synonymous with X8 in the general formula (8) above, * is a single bond that connects to a monovalent group represented by the general formula (84) above, R 801 ~R 824 Each of these is independently a monovalent group that is not represented by general formula (84) in general formulas (81-1) to (81-6) above. 801 ~R 824 (This is synonymous with...)
[0843] R that does not form a divalent group represented by the general formulas (82) and (83) and is not a monovalent group represented by the general formula (84) 801 ~R 808 , and R that is not a monovalent group represented by the general formula (84) 811 ~R 814 and R 821 ~R 824 Preferably, each independently, hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms.
[0844] The monovalent group represented by the general formula (84) is preferably represented by the following general formula (85) or general formula (86).
[0845] [ka]
[0846] (In the above general formula (85), R 831 ~R 840 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. The * in general formula (85) above is equivalent to the * in general formula (84) above.
[0847] [ka]
[0848] (In the above general formula (86), Ar 801 , L 801 and L 803 This is Ar in the general formula (84) 801 , L 801 and L 803 It is synonymous with, HAr 801 This structure is represented by the following general formula (87).
[0849] [ka]
[0850] (In the above general formula (87), X 81 is an oxygen atom or a sulfur atom, R 841 ~R 848 One of the following is L 803 It is a single bond that connects to the surface. R is not a single bond 841 ~R 848 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0851] In addition to the compounds listed in International Publication No. 2014 / 104144, specific examples of compounds represented by the general formula (8) include the following compounds.
[0852] [ka]
[0853] [ka]
[0854] [ka]
[0855] [ka]
[0856] [ka]
[0857] [ka]
[0858] (Compound represented by general formula (9)) This section describes compounds represented by general formula (9).
[0859] [ka]
[0860] (In the above general formula (9), A 91 Ring and A 92 Each ring is independent of the others. A substituted or unsubstituted ring-forming aromatic hydrocarbon ring with 6 to 50 carbon atoms, or These are heterocycles with 5 to 50 ring-forming atoms, either substituted or unsubstituted. A 91 Ring and A 92 One or more rings selected from the group of rings are: It combines with * in the structure represented by the general formula (92) below.
[0861] [ka]
[0862] (In the above general formula (92), A 93 The ring is, A substituted or unsubstituted ring-forming aromatic hydrocarbon ring with 6 to 50 carbon atoms, or These are heterocycles with 5 to 50 ring-forming atoms, either substituted or unsubstituted. X9 is NR 93 , C(R 94 )(R 95 ), Si(R 96 )(R 97 ), Ge(R 98 )(R 99 ), an oxygen atom, a sulfur atom, or a selenium atom, R 91 and R 92 teeth, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 91 and R 92 , and R 93 ~R 99 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0863] A 91 Ring and A 92 One or more rings selected from the group consisting of rings are bonded to * of the structure represented by the general formula (92). That is, in one embodiment, A 91 The ring-forming carbon atoms of the aromatic hydrocarbon ring or the ring-forming atoms of the heterocycle are bonded to * in the structure represented by the general formula (92). In one embodiment, A 92 The ring-forming carbon atoms of the aromatic hydrocarbon ring or the ring-forming atoms of the heterocycle are bonded to * in the structure represented by the general formula (92).
[0864] In one embodiment, A 91 Ring and A 92A group represented by the following general formula (93) is bonded to either or both of the rings.
[0865] [ka]
[0866] (In the above general formula (93), Ar 91 and Ar 92 Each of them operates independently. A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. L 91 ~L 93 Each of them operates independently. single bond, Substituted or unsubstituted ring-forming arylene groups with 6 to 30 carbon atoms, A substituted or unsubstituted divalent heterocyclic group with 5 to 30 ring-forming atoms, or A divalent linking group formed by bonding 2 to 4 atoms selected from the group consisting of substituted or unsubstituted arylene groups with 6 to 30 ring-forming carbon atoms and substituted or unsubstituted divalent heterocyclic groups with 5 to 30 ring-forming atoms. In the general formula (93) above, * represents A 91 Ring and A 92 (This indicates the bonding position with any of the rings.)
[0867] In one embodiment, A 91 In addition to the ring, A 92 The ring-forming carbon atoms of the aromatic hydrocarbon ring or the ring-forming atoms of the heterocycle are bonded to * of the structure represented by the general formula (92). In this case, the structures represented by the general formula (92) may be the same or different from each other.
[0868] In one embodiment, R 91 and R 92 These are, independently, substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms. In one embodiment, R 91 and R92 These combine with each other to form a fluorene structure.
[0869] In one embodiment, ring A 91 and ring A 92 Each of these is independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, for example, a substituted or unsubstituted benzene ring.
[0870] In one embodiment, ring A 93 This refers to a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, such as a substituted or unsubstituted benzene ring. In one embodiment, X9 is an oxygen atom or a sulfur atom.
[0871] Examples of compounds represented by the general formula (9) include the following compounds.
[0872] [ka]
[0873] [ka]
[0874] [ka]
[0875] [ka]
[0876] (Compounds represented by general formula (10)) This section describes the compound represented by general formula (10).
[0877] [ka]
[0878] [ka]
[0879] (In the above general formula (10), The Ax1 ring is a ring represented by the general formula (10a) that condenses at any position of the adjacent ring, The Ax2 ring is a ring represented by the general formula (10b) that condenses at any position of the adjacent ring, The two * in the general formula (10b) above are bonded to any position in the Ax3 ring, X A and X B Each of them independently, C(R 1003 )(R 1004 ), Si(R 1005 )(R 1006 ), an oxygen atom or a sulfur atom, The Ax3 ring is, A substituted or unsubstituted ring-forming aromatic hydrocarbon ring with 6 to 50 carbon atoms, or These are heterocycles with 5 to 50 ring-forming atoms, either substituted or unsubstituted. Ar 1001 teeth, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 1001 ~R 1006 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. mx1 is 3, and mx2 is 2. Multiple R 1001 They are either identical or different from each other. Multiple R 1002 They are either identical or different from each other. ax is 0, 1, or 2. If ax is 0 or 1, the structures in parentheses represented by "3-ax" are either identical or different from each other. If ax is 2, multiple Ar 1001 They are either identical or different to one another.
[0880] In one embodiment, Ar 1001 These are substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms.
[0881] In one embodiment, the Ax3 ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, such as a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted anthracene ring.
[0882] In one embodiment, R 1003 and R 1004 Each of these is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[0883] In one embodiment, ax is 1.
[0884] Examples of compounds represented by the general formula (10) include the following compounds.
[0885] [ka]
[0886] In one embodiment, the light-emitting layer is composed of at least one of the third compound and the fourth compound, The compound represented by the general formula (4) above, The compound represented by the general formula (5) above, The compound represented by the general formula (7) above, The compound represented by the general formula (8) above, The compound represented by the general formula (9) and It contains one or more compounds selected from the group consisting of compounds represented by the following general formula (63a).
[0887] [ka]
[0888] (In the above general formula (63a), R 631 R 646 It combines with to form a substituted or unsubstituted heterocyclic ring, or it does not form a substituted or unsubstituted heterocyclic ring. R 633 R 647 It combines with to form a substituted or unsubstituted heterocyclic ring, or it does not form a substituted or unsubstituted heterocyclic ring. R 634 R 651 It combines with to form a substituted or unsubstituted heterocyclic ring, or it does not form a substituted or unsubstituted heterocyclic ring. R 641 R 642 It combines with to form a substituted or unsubstituted heterocyclic ring, or it does not form a substituted or unsubstituted heterocyclic ring. R 631 ~R 651 Two or more adjacent pairs of these are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted heterocycle, does not form the aforementioned substituted or unsubstituted monocycle, and does not form the aforementioned substituted or unsubstituted fused ring. 631 ~R 651 Each of them operates independently. hydrogen atom, halogen atom, Cyano group, Nitro group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, However, R does not form the substituted or unsubstituted heterocycle, nor does it form the substituted or unsubstituted monocycle, nor does it form the substituted or unsubstituted fused ring. 631 ~R 651 At least one of them is halogen atom, Cyano group, Nitro group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0889] 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), wherein the A1 ring in general formula (41-5) is a substituted or unsubstituted condensed aromatic hydrocarbon ring having 10 to 50 ring-forming carbon atoms, or a substituted or unsubstituted condensed heterocycle having 8 to 50 ring-forming atoms.
[0890] In one embodiment, the substituted or unsubstituted ring-forming condensed aromatic hydrocarbon ring having 10 to 50 carbon atoms in general formulas (41-3), (41-4), and (41-5) is Substituted or unsubstituted naphthalene rings, A substituted or unsubstituted anthracene ring, A substituted or unsubstituted fluorene ring, The aforementioned substituted or unsubstituted fused heterocycles having 8 to 50 ring-forming atoms, Substituted or unsubstituted dibenzofuran rings, A substituted or unsubstituted carbazole ring, It is a substituted or unsubstituted dibenzothiophene ring.
[0891] In one embodiment, the substituted or unsubstituted ring-forming condensed aromatic hydrocarbon ring having 10 to 50 carbon atoms in general formula (41-3), general formula (41-4), or general formula (41-5) is A substituted or unsubstituted naphthalene ring, A substituted or unsubstituted fluorene ring, The aforementioned substituted or unsubstituted fused heterocycles having 8 to 50 ring-forming atoms, Substituted or unsubstituted dibenzofuran rings, A substituted or unsubstituted carbazole ring, It is a substituted or unsubstituted dibenzothiophene ring.
[0892] In one embodiment, the compound represented by the general formula (4) is Compounds represented by the following general formula (461), Compounds represented by the following general formula (462), Compounds represented by the following general formula (463), Compounds represented by the following general formula (464), Compounds represented by the following general formula (465), Compounds represented by the following general formula (466), and The compounds are selected from the group consisting of compounds represented by the following general formula (467).
[0893] [ka]
[0894] [ka]
[0895] [ka]
[0896] [ka]
[0897] [ka]
[0898] (In the above general formulas (461) to (467), R 421 ~R 427 , R 431 ~R 436 , R 440 ~R 448 and R 451 ~R 454 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R 437 , R 438 , and R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring 421 ~R 427 , R 431 ~R 436 , R 440 ~R 448 and R 451 ~R 454 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. X4 is an oxygen atom, NR 801 , or C(R 802 )(R 803 ) and R 801 , R 802 and R 803 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, R 801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 They are either identical or different from one another. R 803 If multiple R 803 They are either identical or different to one another.
[0899] In one embodiment, R 421 ~R 427 and R 440 ~R 448 However, each independently, hydrogen atom, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms.
[0900] In one embodiment, R 421 ~R 427 and R 440 ~R 447 However, each independently, hydrogen atom, Substituted or unsubstituted ring-forming aryl groups with 6 to 18 carbon atoms, and The group consists of heterocyclic groups with 5 to 18 ring-forming atoms, either substituted or unsubstituted.
[0901] In one embodiment, the compound represented by the general formula (41-3) is the compound represented by the following general formula (41-3-1).
[0902] [ka]
[0903] (In the above general formula (41-3-1), R 423 , R 425 , R 426 , R 442 , R 444 and R 445 Each of these independently corresponds to R in the general formula (41-3) above. 423 , R 425 , R 426 , R 442 , R 444 and R 445 (This is synonymous with...)
[0904] In one embodiment, the compound represented by the general formula (41-3) is the compound represented by the following general formula (41-3-2).
[0905] [ka]
[0906] (In the above general formula (41-3-2), R 421 ~R 427 and R 440 ~R 448Each of these independently corresponds to R in the general formula (41-3) above. 421 ~R 427 and R 440 ~R 448 It is synonymous with, However, R 421 ~R 427 and R 440 ~R 446 At least one of them is -N(R 906 )(R 907 It is a base represented by ).
[0907] In one embodiment, in formula (41-3-2), R 421 ~R 427 and R 440 ~R 446 Any two of the following are -N(R 906 )(R 907 It is a base represented by ).
[0908] In one embodiment, the compound represented by formula (41-3-2) is the compound represented by the following formula (41-3-3).
[0909] [ka]
[0910] (In the above general formula (41-3-3), R 421 ~R 424 , R 440 ~R 443 , R 447 and R 448 Each of these independently corresponds to R in the general formula (41-3) above. 421 ~R 424 , R 440 ~R 443 , R 447 and R 448 It is synonymous with, R A , R B , R C and R D Each of them operates independently. A substituted or unsubstituted ring-forming aryl group having 6 to 18 carbon atoms, or It is a heterocyclic group with 5 to 18 ring-forming atoms, either substituted or unsubstituted.
[0911] In one embodiment, the compound represented by formula (41-3-3) is the compound represented by the following formula (41-3-4).
[0912] [ka]
[0913] (In the above general formula (41-3-4), R 447 , R 448 , R A , R B , R C and R D Each of these independently corresponds to R in equation (41-3-3) above. 447 , R 448 , R A , R B , R C and R D (This is synonymous with...)
[0914] In one embodiment, R A , R B , R C and R D However, each of these is independently a substituted or unsubstituted ring-forming aryl group with 6 to 18 carbon atoms.
[0915] In one embodiment, R A , R B , R C and R D However, each is independently a substituted or unsubstituted phenyl group.
[0916] In one embodiment, R 447 and R 448 However, it is a hydrogen atom.
[0917] In one embodiment, the substituent in the case of "substituted or unsubstituted" in each of the above formulas is Unsubstituted alkyl groups with 1 to 50 carbon atoms, Unsubstituted alkenyl groups with 2 to 50 carbon atoms, Unsubstituted alkynyl groups with 2 to 50 carbon atoms, Unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901a )(R 902a )(R 903a ), -O-(R 904a ), -S-(R 905a ), -N(R 906a )(R 907a ), halogen atom, Cyano group, Nitro group, Unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, or It is an unsubstituted heterocyclic group with 5 to 50 ring-forming atoms. R 901a ~R 907a Each of them operates independently. hydrogen atom, Unsubstituted alkyl groups with 1 to 50 carbon atoms, Unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, or It is an unsubstituted heterocyclic group with 5 to 50 ring-forming atoms. R 901a If there are 2 or more of them, then there are 2 or more R 901a They are either identical or different from each other. R 902a If there are 2 or more of them, then there are 2 or more R 902a They are either identical or different from each other. R 903a If there are 2 or more of them, then there are 2 or more R 903a They are either identical or different from each other. R 904a If there are 2 or more of them, then there are 2 or more R 904a They are either identical or different from each other. R 905a If there are 2 or more of them, then there are 2 or more R 905a They are either identical or different from each other. R 906a If there are 2 or more of them, then there are 2 or more R 906aThey are either identical or different from each other. R 907a If there are 2 or more of them, then there are 2 or more R 907a They are either identical or different from one another.
[0918] In one embodiment, the substituent in the case of "substituted or unsubstituted" in each of the above formulas is Unsubstituted alkyl groups with 1 to 50 carbon atoms, Unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, or It is an unsubstituted heterocyclic group with 5 to 50 ring-forming atoms.
[0919] In one embodiment, the substituent in the case of "substituted or unsubstituted" in each of the above formulas is Unsubstituted alkyl groups with 1 to 18 carbon atoms, Unsubstituted ring-forming aryl groups with 6 to 18 carbon atoms, or It is an unsubstituted heterocyclic group with 5 to 18 ring-forming atoms.
[0920] In the organic EL element according to this embodiment, the first light-emitting layer further contains a third fluorescent compound, and the third compound is preferably a compound that exhibits light emission with a main peak wavelength of 430 nm or more and 480 nm or less.
[0921] In the organic EL element according to this embodiment, the second light-emitting layer further contains a fluorescent fourth compound, and the fourth compound is preferably a compound that exhibits light emission with a main peak wavelength of 430 nm or more and 480 nm or less.
[0922] The method for measuring the main peak wavelength of a compound is as follows: 10 -6 mol / L or more 10 -5 Prepare a toluene solution with a concentration of mol / L or less and place it in a quartz cell. Measure the emission spectrum of this sample at room temperature (300K) (vertical axis: emission intensity, horizontal axis: wavelength). The emission spectrum can be measured using a spectrophotometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measuring device is not limited to the device used here. In the emission spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is defined as the primary emission peak wavelength. In this specification, the primary peak wavelength may be referred to as the fluorescence emission primary peak wavelength (FL-peak).
[0923] In the organic EL element according to this embodiment, when the first light-emitting layer includes a first compound and a 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, emitter, or light-emitting material).
[0924] In the organic EL element according to this embodiment, when the first light-emitting layer contains a first compound and a third compound, it is preferable that the singlet energy S1(H1) of the first compound and the singlet energy S1(D3) of the third compound satisfy the relationship shown in the following formula (Equation 1). S1(H1)>S1(D3)...(Math 1)
[0925] In the organic EL element according to this embodiment, if the second light-emitting layer contains a second compound and a 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, emitter, or light-emitting material).
[0926] In the organic EL element according to this embodiment, when the second light-emitting layer contains a second compound and a fourth compound, it is preferable that the singlet energy S1(H2) of the second compound and the singlet energy S1(D4) of the fourth compound satisfy the relationship shown in the following formula (Equation 2). S1(H2)>S1(D4)...(Math 2)
[0927] (Singlet energy S1) The following methods can be used to measure the singlet energy S1 using a solution (sometimes referred to as the solution method). 10 compounds to be measured-5 mol / L or more 10 -4 Prepare a toluene solution with a concentration of mol / L or less and place it in a quartz cell. Measure the absorption spectrum of this sample at room temperature (300K) (vertical axis: absorption intensity, horizontal axis: wavelength). Draw a tangent line to the falling edge of the absorption spectrum at longer wavelengths, and substitute the wavelength value λedge [nm] at the intersection of the tangent line and the horizontal axis into the following conversion formula (F2) to calculate the singlet energy. Conversion formula (F2): S1[eV]=1239.85 / λedge Examples of absorption spectrum measuring devices include, but are not limited to, Hitachi's spectrophotometer (device name: U3310).
[0928] The tangent to the falling edge of an absorption spectrum on the longer wavelength side is drawn as follows: Consider the tangents at each point on the spectral curve as we move along the spectral curve in the longer wavelength direction from the maximum value on the longest wavelength side of the absorption spectrum. As the curve falls (i.e., as the value on the vertical axis decreases), the slope of this tangent decreases and then increases repeatedly. The tangent drawn at the point where the value of the slope is minimized on the longest wavelength side (except when the absorbance is 0.1 or less) is taken as the tangent to the falling edge of the absorption spectrum on the longer wavelength side. Note that maximum absorbance values of 0.2 or less are not included in the maximum value at the longest wavelength mentioned above.
[0929] In the organic EL element according to this 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 relationship shown in the following formula (Equation 3). μH2 > μH1 ... (Math 3)
[0930] The relationship between the first compound and the second compound, as shown in the above formula (Equation 3), improves the recombination ability of holes and electrons in the first light-emitting layer.
[0931] Electron mobility can be measured using impedance spectroscopy in the following way. A measurement target layer with a thickness of 100 nm to 200 nm is sandwiched between the anode and cathode, and a small AC voltage of 100 mV or less is applied while a bias DC voltage is applied. The value of the AC current (absolute value and phase) that flows at this time is measured. This measurement is performed while changing the frequency of the AC voltage, and the complex impedance (Z) is calculated from the current value and voltage value. At this time, the frequency dependence of the imaginary part (ImM) of the modulus M = iωZ (i: imaginary unit, ω: angular frequency) is determined, and the reciprocal of the frequency ω at which ImM is maximum is defined as the response time of electrons conducting within the measurement target layer. Then, the electron mobility is calculated using the following formula. Electron mobility = (film thickness of the layer being measured) 2 (Response time · Voltage)
[0932] The first and second light-emitting layers preferably do not contain phosphorescent materials (dopant materials). Furthermore, it is preferable that the first and second light-emitting layers do not contain heavy metal complexes and phosphorescent rare-earth metal complexes. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes. Furthermore, it is preferable that the first and second light-emitting layers do not contain metal complexes.
[0933] (film thickness of the light-emitting layer) The film thickness of the light-emitting layer of the organic EL element according to this embodiment is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and even more preferably 10 nm or more and 50 nm or less. When the film thickness of the light-emitting layer is 5 nm or more, it is easy to form the light-emitting layer and easy to adjust the chromaticity. When the film thickness of the light-emitting layer is 50 nm or less, it is easy to suppress the rise in the driving voltage.
[0934] (Compound content in the luminescent layer) When the first light-emitting layer contains the first compound and the third compound, the content of the first compound and the third compound in the first light-emitting layer is preferably, for example, within the following ranges. The content 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 even more preferably 95% by mass or more and 99% by mass or less. The content 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 even more preferably 1% by mass or more and 5% by mass or less. However, the upper limit of the total content of the first compound and the third compound in the first light-emitting layer is 100% by mass.
[0935] This embodiment does not exclude the possibility that the first light-emitting layer may contain materials other than the first compound and the third compound. The first light-emitting layer may contain only one type of the first compound, or two or more types. The first light-emitting layer may contain only one type of the third compound, or two or more types.
[0936] When the second light-emitting layer contains the second compound and the fourth compound, the content of the second compound and the fourth compound in the second light-emitting layer is preferably, for example, within the following ranges. The content 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 even more preferably 95% by mass or more and 99% by mass or less. The content 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 even more preferably 1% by mass or more and 5% by mass or less. However, the upper limit of the total content of the second compound and the fourth compound in the second light-emitting layer is 100% by mass.
[0937] This embodiment does not exclude the possibility that the second light-emitting layer may contain materials other than the second compound and the fourth compound. The second light-emitting layer may contain only one type of the second compound, or two or more types. The second light-emitting layer may contain only one type of the fourth compound, or two or more types.
[0938] The configuration of the organic EL element will be explained further below. In the following text, symbols may be omitted.
[0939] (substrate) The substrate is used as a support for the organic EL element. Examples of substrates include glass, quartz, and plastic. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), such as a plastic substrate. Examples of materials for forming a plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. An inorganic vapor-deposited film may also be used.
[0940] (anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof with a large work function (specifically, 4.0 eV or more). Specifically, examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene, etc. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metallic materials (e.g., titanium nitride).
[0941] These materials are typically deposited by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1% to 10% by mass of zinc oxide relative to indium oxide. Similarly, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5% to 5% by mass of tungsten oxide and 0.1% to 1% by mass of zinc oxide relative to indium oxide. Other methods such as vacuum deposition, coating, inkjet, and spin coating may also be used.
[0942] Of the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that facilitates hole injection regardless of the anode's work function. Therefore, any material suitable for electrode materials (e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used.
[0943] Materials with low work functions, such as elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these, can also be used. When forming an anode using alkali metals, alkaline earth metals, or alloys containing these, vacuum deposition or sputtering methods can be used. Furthermore, when using silver paste or similar materials, coating methods or inkjet methods can be employed.
[0944] (cathode) For the cathode, it is preferable to use metals, alloys, electrically conductive compounds, and mixtures thereof with a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.
[0945] Furthermore, when forming a cathode using alkali metals, alkaline earth metals, or alloys containing these, vacuum deposition or sputtering methods can be used. Additionally, when using silver paste or similar materials, coating or inkjet methods can be employed.
[0946] Furthermore, by providing an electron injection layer, cathodes can be formed using various conductive materials such as Al, Ag, ITO, graphene, silicon, or indium tin oxide containing silicon oxide, regardless of the magnitude of the work function. These conductive materials can be deposited using methods such as sputtering, inkjet printing, or spin coating.
[0947] (Hole injection layer) The hole injection layer is a layer containing a material with high hole injection properties. Suitable materials with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.
[0948] Furthermore, substances with high hole injection potential include low-molecular-weight organic compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviated as TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviated as DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino] Aromatic amine compounds such as [phenylaminobenzene] (abbreviated as DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviated as PCzPCN1) are also examples, as is dipyradino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonnitrile (HAT-CN).
[0949] Furthermore, polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used as materials with high hole injection properties. Examples of polymer compounds include poly(N-vinylcarbazole) (abbreviated as PVK), poly(4-vinyltriphenylamine) (abbreviated as PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated as PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated as Poly-TPD). In addition, polymer compounds to which acids such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS) have been added can also be used.
[0950] (Hole transport layer) The hole transport layer is a layer containing a substance with high hole transport properties. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used in the hole transport layer. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl Aromatic amine compounds such as phenyl (abbreviated as DFLDPBi), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviated as TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB) can be used. The substances described here are mainly 10 -6 cm 2 It is a substance having a hole mobility of / (V·s) or greater.
[0951] The hole transport layer may use carbazole derivatives such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (PCzPA), or anthracene derivatives such as t-BuDNA, DNA, and DPAnth. High molecular weight compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) can also be used.
[0952] However, other materials may be used as long as they have higher hole transport capabilities than electron transport capabilities. Furthermore, the layer containing the material with high hole transport capabilities may be a single layer, or it may consist of two or more layers of the above-mentioned material stacked together.
[0953] (electron transport layer) The electron transport layer is a layer containing a material with high electron transport properties. The electron transport layer can contain: 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) polymer compounds. Specifically, low-molecular-weight organic compounds such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviated as BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ, among others, can be used. In addition to metal complexes, there are also 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: Heteroaromatic compounds such as (TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), vasophenanthroline (abbreviated as BPhen), vasocuproin (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazole-2-yl)stilbene (abbreviated as BzOs) can also be used. In this embodiment, benzimidazole compounds can be suitably used. The substances described herein are mainly 10 -6 cm 2 The material has an electron mobility of 1 / (V·s) or greater. However, any material with higher electron transport properties than hole transport properties may be used as the electron transport layer. Furthermore, the electron transport layer may consist of a single layer, or it may consist of two or more layers of the above material stacked together.
[0954] Specific examples of compounds that can be used in electron transport layers include the following compounds. However, the present invention is not limited to these specific examples of compounds.
[0955] [ka]
[0956] Furthermore, polymer compounds can also be used in the electron transport layer. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy) can be used.
[0957] (electron injection layer) The electron injection layer is a layer containing a material with high electron injection potential. The electron injection layer can contain alkali metals, alkaline earth metals, or compounds thereof, such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiOx). Alternatively, a material containing an alkali metal, alkaline earth metal, or compound thereof in an electron-transporting material, specifically one containing magnesium (Mg) in Alq, may also be used. In this case, electron injection from the cathode can be performed more efficiently.
[0958] Alternatively, a composite material formed by mixing an organic compound and an electron donor may be used in the electron injection layer. Such a composite material exhibits excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material that is excellent at transporting the generated electrons, and specifically, for example, the substances that constitute the electron transport layer described above (metal complexes, heteroaromatic compounds, etc.) can be used. The electron donor can be any substance that exhibits electron-donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. Alkali metal oxides and alkaline earth metal oxides are also preferred, such as lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide can also be used. Organic compounds such as tetrathiafulvalene (abbreviated as TTF) can also be used.
[0959] (Layer formation method) The method for forming each layer of the organic EL element in this embodiment is not limited to those specifically mentioned above, but known methods such as dry deposition methods such as vacuum deposition, sputtering, plasma deposition, and ion plating, and wet deposition methods such as spin coating, dipping, flow coating, and inkjet deposition can be employed.
[0960] (film thickness) The film thickness of each organic layer in the organic EL element of this embodiment is not limited unless otherwise specifically mentioned above. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and if the film thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, the film thickness of each organic layer in the organic EL element is usually preferably in the range of a few nanometers to 1 μm.
[0961] (Emission wavelength of organic EL elements) In this embodiment, the organic electroluminescent element preferably emits light with a main peak wavelength of 430 nm to 480 nm when the element is driven. The main peak wavelength of light emitted by the organic EL element during element drive is measured as follows: Current density is 10 mA / cm². 2 The spectral radiance spectrum of an organic EL element is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta) when a voltage is applied to the element in such a manner. The peak wavelength of the emission spectrum with the maximum emission intensity is measured from the obtained spectral radiance spectrum and defined as the main peak wavelength (unit: nm).
[0962] The organic EL element according to this embodiment can improve element performance. Furthermore, in the organic EL element according to the embodiment in which multiple light-emitting layers are stacked, since the light-emitting layer on the anode side (first light-emitting layer) contains the compound according to the first embodiment, it is expected that a good balance between luminous efficiency and lifespan will be achieved.
[0963] [Fourth Embodiment] (electronic equipment) The electronic device according to this embodiment is equipped with an organic EL element according to any of the embodiments described above. Examples of electronic devices include display devices and light-emitting devices. Examples of display devices include display components (e.g., organic EL panel modules), televisions, mobile phones, tablets, and personal computers. Examples of light-emitting devices include lighting and vehicle lights.
[0964] [Changes to the embodiment] Furthermore, the present invention is not limited to the embodiments described above, and any modifications, improvements, etc., that can achieve the objectives of the present invention are included in the present invention.
[0965] For example, the light-emitting layer is not limited to one layer or two layers, but may consist of more than two stacked light-emitting layers. When an organic EL element has multiple light-emitting layers, it is sufficient if one light-emitting layer satisfies the conditions described in the above embodiment, or if two light-emitting layers satisfy the conditions described in the above embodiment. For example, the other light-emitting layers may be fluorescent light-emitting layers, or phosphorescent light-emitting layers that utilize light emission due to electron transitions from a triplet excited state to a direct ground state. Furthermore, if the organic EL element has multiple light-emitting layers, these light-emitting layers may be arranged adjacent to each other, or it may be a so-called tandem type organic EL element in which multiple light-emitting units are stacked with an intermediate layer in between.
[0966] Alternatively, for example, a barrier layer may be provided adjacent to at least one of the anode and cathode sides of the light-emitting layer. The barrier layer is preferably positioned in contact with the light-emitting layer and blocks at least one of holes, electrons, and excitons. For example, if a barrier layer is placed in contact with the cathode side of the light-emitting layer, the barrier layer transports electrons and prevents holes from reaching the layer on the cathode side of the barrier layer (e.g., the electron transport layer). If the organic EL element includes an electron transport layer, it is preferable to include the barrier layer between the light-emitting layer and the electron transport layer. Furthermore, if a barrier layer is placed in contact with the anode side of the light-emitting layer, the barrier layer transports holes and prevents electrons from reaching the layer on the anode side of the barrier layer (for example, a hole transport layer). If the organic EL element includes a hole transport layer, it is preferable to include the barrier layer between the light-emitting layer and the hole transport layer. Furthermore, a barrier layer may be provided adjacent to the light-emitting layer to prevent excitation energy from leaking from the light-emitting layer to the surrounding layers. This barrier layer prevents excitons generated in the light-emitting layer from moving to layers closer to the electrodes (for example, electron transport layers and hole transport layers). It is preferable that the light-emitting layer and the barrier layer are bonded together.
[0967] Furthermore, the specific structure and shape in the implementation of the present invention may be other structures, etc., to the extent that the objectives of the present invention can be achieved. [Examples]
[0968] The present invention will be described in more detail below with reference to examples. The present invention is not limited to these examples.
[0969] <Compound> The structures of the compounds represented by the general formula (1000B) used in the manufacture of organic EL elements in Examples 1 to 31 are shown below.
[0970] [ka]
[0971] [ka]
[0972] [ka]
[0973] [ka]
[0974] [ka]
[0975] [ka]
[0976] The structures of the compounds used in the manufacture of the organic EL elements in Comparative Examples 4 to 7 are shown below.
[0977] [ka]
[0978] The structures of other compounds used in the production of organic EL elements in Examples 1-31 and Comparative Examples 1-9 are shown below.
[0979] [ka]
[0980] [ka]
[0981] [ka]
[0982] [ka]
[0983] [ka]
[0984] <Fabrication of Organic EL Devices> Organic EL elements were fabricated and evaluated as follows.
[0985] (Example 1) A glass substrate (manufactured by Geomatec Co., Ltd.) with a 25mm x 75mm x 1.1mm thick ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was set to 130 nm. After cleaning, the glass substrate with transparent electrode lines was mounted in the substrate holder of the vacuum deposition apparatus. First, compound HIL-1 was deposited on the side where the transparent electrode lines were formed, covering the transparent electrodes, to form a hole injection layer with a thickness of 5 nm. Following the deposition of the hole injection layer, compound HTL-1 was deposited to form a first hole transport layer with a thickness of 80 nm. Following the deposition of the first hole transport layer, compound EBL-1 was deposited to create a second hole transport layer (also called an electron barrier layer) with a thickness of 10 nm. Compound BH1-1 as the first compound and compound BD-1 as the third compound were co-deposited onto the second hole transport layer such that the proportion of compound BD-1 was 2% by mass, thereby forming a first light-emitting layer with a thickness of 5 nm. Compound BH2-3, as the second compound, and compound BD-1, as the fourth compound, were co-deposited onto the first light-emitting layer such that the proportion of compound BD-1 was 2% by mass, thereby forming a second light-emitting layer with a thickness of 20 nm. Compound aET-1 was deposited on the second light-emitting layer to form a first electron transport layer (also called a hole barrier layer) with a thickness of 10 nm. Compound bET-1 was deposited on the first electron transport layer to form a second electron transport layer with a thickness of 15 nm. LiF was deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm. A cathode with a thickness of 80 nm was formed by depositing metallic aluminum onto the electron injection layer. The element configuration of Example 1 is schematically shown below. ITO(130) / HIL-1(5) / HTL-1(80) / EBL-1(10) / BH1-1:BD-1(5,98%:2%) / BH2-3:BD-1(20,98%:2%) / aET-1(10) / bET-1(15) / LiF(1) / Al(80) The numbers in parentheses indicate the film thickness (in nm). Similarly, the percentage figures in parentheses (98%:2%) indicate the proportion (by mass) of compound BH1-1 or BH2-3 and compound BD-1 in the first or second light-emitting layer. The same notation will be used hereafter.
[0986] (Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, and 14) The organic EL elements of Examples 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, and 14 were fabricated in the same manner as in Example 1, except that the first compound of the first light-emitting layer was changed to one of the compounds listed in Table 1.
[0987] (Comparative Example 1) The organic EL element of Comparative Example 1 was fabricated in the same manner as in Example 1, except that a second light-emitting layer with a thickness of 25 nm was formed on the second hole transport layer without forming the first light-emitting layer, as shown in Table 1.
[0988] (Comparative Example 2) The organic EL element of Comparative Example 2 was fabricated in the same manner as in Example 1, except that a first light-emitting layer with a thickness of 25 nm was formed as the light-emitting layer, and a first electron transport layer was formed on the first light-emitting layer without forming a second light-emitting layer, as shown in Table 1.
[0989] (Comparative Examples 3, 4, and 5) The organic EL elements of Comparative Examples 3, 4, and 5 were fabricated in the same manner as Comparative Example 2, except that the first compound of the first light-emitting layer was changed to one of the compounds listed in Table 1.
[0990] (Comparative Examples 6 and 7) The organic EL elements of Comparative Examples 6 and 7 were prepared in the same manner as in Example 1, except that the first compound of the first light-emitting layer was changed to one of the compounds listed in Table 1.
[0991] [Table 1]
[0992] <Evaluation of Organic EL Devices> The organic EL elements fabricated in Examples 1-31 and Comparative Examples 1-9 were evaluated as follows. The evaluation results are shown in Tables 1, 2, 3, and 4.
[0993] • External quantum efficiency (EQE) Current density is 10 mA / cm² 2 The spectral radiance spectrum was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) when a voltage was applied to the element in such a manner. From the obtained spectral radiance spectrum, the external quantum efficiency EQE (unit: %) was calculated assuming that lambassian emission occurred.
[0994] ·Life span (LT95) The resulting organic EL element has a current density of 50 mA / cm². 2 A voltage was applied to achieve the desired result, and the time it took for the brightness to reach 95% of the initial brightness (LT95 (unit: hours)) was measured.
[0995] (Example 15) The organic EL element of Example 15 was manufactured in the same manner as in Example 1, except that the third compound of the first light-emitting layer and the fourth compound of the second light-emitting layer were replaced with the compounds listed in Table 2, respectively.
[0996] (Examples 16, 17, 18, 19, 20, 21, 22, 23, and 24) The organic EL elements of Examples 16, 17, 18, 19, 20, 21, 22, 23, and 24 were fabricated in the same manner as in Example 15, except that the first compound of the first light-emitting layer was changed to one of the compounds listed in Table 2.
[0997] (Comparative Example 8) The organic EL element of Comparative Example 8 was fabricated in the same manner as in Example 15, except that, as shown in Table 2, a second light-emitting layer with a thickness of 25 nm was formed on the second hole transport layer without forming the first light-emitting layer.
[0998] [Table 2]
[0999] (Example 25) A glass substrate (manufactured by Geomatec Co., Ltd.) with a 25mm x 75mm x 1.1mm thick ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was set to 130 nm. After cleaning, a glass substrate with transparent electrode lines was mounted in the substrate holder of a vacuum deposition apparatus. First, compounds HTL-2 and HIL-2 were co-deposited onto the surface on which the transparent electrode lines were formed, covering the transparent electrodes, to form a hole injection layer with a thickness of 10 nm. The proportion of compound HTL-2 in this hole injection layer was set to 90% by mass, and the proportion of compound HIL-2 was set to 10% by mass. Following the deposition of the hole injection layer, compound HTL-2 was deposited to form a first hole transport layer with a thickness of 85 nm. Following the deposition of the first hole transport layer, compound EBL-2 was deposited to create a second hole transport layer (also called an electron barrier layer) with a thickness of 5 nm. Compound BH1-1, as the first compound, and compound BD-2, as the third compound, were co-deposited onto the second hole transport layer such that the proportion of compound BD-2 was 2% by mass, thereby forming a first light-emitting layer with a thickness of 5 nm. Compound BH2-4, as the second compound, and compound BD-2, as the fourth compound, were co-deposited onto the first light-emitting layer such that the proportion of compound BD-2 was 2% by mass, thereby forming a second light-emitting layer with a thickness of 15 nm. Compound aET-2 was deposited on the second light-emitting layer to form a first electron transport layer (also called a hole barrier layer) with a thickness of 5 nm. Compound bET-2 and compound Liq were co-deposited onto the first electron transport layer to form a second electron transport layer with a thickness of 25 nm. The proportion of compound bET-2 in this second electron transport layer was set to 50% by mass, and the proportion of compound Liq was set to 50% by mass. Liq is an abbreviation for (8-Quinolinolato)lithium. A compound Liq was deposited onto the second electron transport layer to form an electron injection layer with a thickness of 1 nm. A cathode with a thickness of 80 nm was formed by depositing metallic aluminum onto the electron injection layer. The element configuration of Example 25 is schematically shown below. ITO(130) / HTL-2:HIL-2(10,90%:10%) / HTL-2(85) / EBL-2(5) / BH1-1:BD-2(5,98%: 2%) / BH2-4:BD-2(15,98%:2%) / aET-2(5) / bET-2:Liq(25,50%:50%) / Liq(1) / Al(80) The numbers in parentheses indicate the film thickness (in nm). Similarly, within the parentheses, the percentage figures (90%:10%) indicate the proportion (mass%) of compounds HTL-2 and HIL-2 in the hole injection layer, the percentage figures (98%:2%) indicate the proportion (mass%) of BH1-1 or BH2-4 and compound BD-2 in the first or second light-emitting layer, and the percentage figures (50%:50%) indicate the proportion (mass%) of compounds bET-2 and Liq in the second electron transport layer. The same notation will be used hereafter.
[1000] (Comparative Example 9) The organic EL element of Comparative Example 9 was fabricated in the same manner as in Example 25, except that, as shown in Table 3, a second light-emitting layer with a thickness of 20 nm was formed on the second hole transport layer without forming the first light-emitting layer.
[1001] [Table 3]
[1002] (Example 26) A glass substrate (manufactured by Geomatec Co., Ltd.) with a 25mm x 75mm x 1.1mm thick ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was set to 130 nm. After cleaning, the glass substrate with transparent electrode lines was mounted in the substrate holder of the vacuum deposition apparatus. First, compound HIL-1 was deposited on the side where the transparent electrode lines were formed, covering the transparent electrodes, to form a hole injection layer with a thickness of 5 nm. Following the deposition of the hole injection layer, compound HTL-1 was deposited to form a first hole transport layer with a thickness of 80 nm. Following the deposition of the first hole transport layer, compound EBL-1 was deposited to create a second hole transport layer (also called an electron barrier layer) with a thickness of 10 nm. Compound BH1-22, as the first compound, and compound BD-1, as the third compound, were co-deposited onto the second hole transport layer such that the proportion of compound BD-1 was 2% by mass, thereby forming a first light-emitting layer with a thickness of 5 nm. Compound BH2-3, as the second compound, and compound BD-1, as the fourth compound, were co-deposited onto the first light-emitting layer such that the proportion of compound BD-1 was 2% by mass, thereby forming a second light-emitting layer with a thickness of 20 nm. Compound aET-1 was deposited on the second light-emitting layer to form a first electron transport layer (also called a hole barrier layer) with a thickness of 10 nm. Compound bET-1 was deposited on the first electron transport layer to form a second electron transport layer with a thickness of 15 nm. LiF was deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm. A cathode with a thickness of 80 nm was formed by depositing metallic aluminum onto the electron injection layer. The element configuration of Example 26 is schematically shown below. ITO(130) / HIL-1(5) / HTL-1(80) / EBL-1(10) / BH1-22:BD-1(5,98%:2%) / BH2-3:BD-1(20,98%:2%) / aET-1(10) / bET-1(15) / LiF(1) / Al(80) The numbers in parentheses indicate the film thickness (in nm). Similarly, the percentage figures in parentheses (98%:2%) indicate the proportion (by mass) of compound BH1-22 or BH2-3 and compound BD-1 in the first or second light-emitting layer. The same notation will be used hereafter.
[1003] (Examples 27, 28, 29, 30, and 31) The organic EL elements of Examples 27, 28, 29, 30, and 31 were fabricated in the same manner as in Example 26, except that the first compound of the first light-emitting layer was changed to one of the compounds listed in Table 4.
[1004] [Table 4]
[1005] <Synthesis of Compound> <Synthesis Example 1: Synthesis of Compound BH1-1> Compound BH1-1 was synthesized according to the following synthetic route.
[1006]
Chemical Structure
[1007] (Synthesis of Intermediate M1) Under an argon atmosphere, 8.21 g of 3,5-dibromo-1,1'-biphenyl, 5.52 g of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[kl]xanthene synthesized by a known method, 0.82 g of tetrakis(triphenylphosphine)palladium(0), 4.22 g of sodium carbonate, 150 mL of 1,4-dioxane, and 40 mL of water were placed in a three-necked flask and refluxed with stirring for 8 hours. After refluxing with stirring, it was cooled to room temperature. After cooling, the precipitated solid was collected by filtration. The obtained solid was washed successively with water and methanol, and then recrystallized repeatedly with toluene to obtain 4.75 g of a pale yellow solid (yield 66%). FD-MS (Field Desorption Mass Spectrometry) analysis was performed on the obtained compound and it was identified as Intermediate M1.
[1008]
Chemical Structure
[1009] (Synthesis of Compound BH1-1) Under an argon atmosphere, 13.21 g of intermediate M1, 2.53 g of pyrene-1-ylboronic acid synthesized by a known method, 0.22 g of tetrakis(triphenylphosphine)palladium(0), 2.22 g of sodium carbonate, 50 mL of 1,4-dioxane, and 10 mL of water were placed in a three-necked flask and refluxed with stirring for 8 hours. After refluxing with stirring, it was cooled to room temperature. After cooling, the precipitated solid was collected by filtration. The obtained solid was washed successively with water and methanol, and then recrystallized with toluene repeatedly to obtain 4.70 g (yield 80%) of a pale yellow solid. As a result of FD-MS analysis, the pale yellow solid was compound BH1-1, and for a molecular weight of 570.69, m / e = 571.
[1010] <Synthesis Example 2: Synthesis of Compound BH1-2> Compound BH1-2 was synthesized according to the following synthetic route.
[1011]
Chemical formula
[1012] (Synthesis of 4-bromobenzo[kl]xanthene) Under an argon atmosphere, 13.5 g of N-bromosuccinimide was added to a mixed solution of 400 mL of dichloromethane and acetonitrile (3:1) containing 15.0 g of benzo[kl]xanthene, and the mixture was stirred at room temperature for 10 minutes. After stirring, the precipitated solid was collected by filtration. The obtained solid was washed with a mixed solvent of acetonitrile and methanol to obtain 15.6 g (77%) of a white solid. As a result of FD-MS analysis, the white solid was compound 4-bromobenzo[kl]xanthene, and for a molecular weight of 297.15, m / e = 298. DCM is an abbreviation for dichloromethane, MeCN is an abbreviation for acetonitrile, and NBS is an abbreviation for N-bromosuccinimide.
[1013]
Chemical formula
[1014] (Synthesis of Compound BH1-2) Under an argon atmosphere, 3.00 g of 4-bromobenzo[kl]xanthene, 3.25 g of (4-(pyrene-1-yl)phenylboronic acid, 0.46 g of tetrakis(triphenylphosphine)palladium(0), 3.21 g of sodium carbonate, 50 mL of 1,4-dioxane, and 15 mL of deionized water were added to a flask and stirred under reflux for 18 hours. After stirring under reflux, the mixture was cooled to room temperature. After cooling, the precipitated solid was filtered. The obtained solid was washed sequentially with water and acetone, and then recrystallized in a mixed solvent of toluene and cyclohexane to obtain a pale yellow solid 2.34 (yield 47%). FD-MS analysis revealed that the pale yellow solid was compound BH1-2, with a molecular weight of 494.59 and a m / e ratio of 495.
[1015] <Synthesis Example 3: Synthesis of Compound BH1-3> Compound BH1-3 was synthesized using the following synthetic route.
[1016] [ka]
[1017] (Synthesis of compound BH1-3) Under an argon atmosphere, 5.00 g of 1,6-dibromopyrene, 9.59 g of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)benzo[kl]xanthene synthesized by a known method, 0.32 g of tetrakis(triphenylphosphine)palladium(0), 2.88 g of sodium carbonate, 60 mL of 1,4-dioxane, and 9.9 mL of water were placed in a three-necked flask and stirred under reflux for 8 hours. After reflux stirring, the mixture was cooled to room temperature. After cooling, the precipitated solid was filtered. The obtained solid was sequentially washed with water and methanol, and then recrystallized repeatedly with toluene to obtain 6.59 g of a pale yellow solid (yield 75%). The obtained compound was analyzed by FD-MS and identified as compound BH1-3.
[1018] <Synthesis Example 4: Synthesis of Compound BH1-4> Compound BH1-4 was synthesized using the following synthetic route.
[1019] [Chemistry]
[1020] (Synthesis of Compound BH1-4) Under an argon atmosphere, 4.00 g of 1-bromopyrene, 3.70 g of benzo[kl]xanthene-10-yl-boronic acid synthesized by a known method, 0.33 g of tetrakis(triphenylphosphine)palladium(0), 3.00 g of sodium carbonate, 61 mL of 1,4-dioxane, and 10.0 mL of water were p...
Claims
1. A compound having at least one group represented by the following general formula (11), and containing exactly one benz[de]anthracene derivative skeleton represented by the following general formula (1000) in its molecule. 【Chemistry 1】 (In the above general formula (1000), X is an oxygen atom, a sulfur atom, C(R) 2001 ) (Caution 2002 ), or Si (R 2003 ) (Caution 2004 ) and R 2001 ~R 2004 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by -N(R) 906 ) (Caution 907 ) a base represented by halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, R 10 ~R 19 Of these, one or more pairs consisting of two or more adjacent items, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 10 ~R 19 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by -N(R) 906 ) (Caution 907 ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by - COOR 802 A base represented by halogen atom, Nitro group, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, or The group is represented by the general formula (11) above, However, R 10 ~R 19 At least one of them is a group represented by the general formula (11), If there are multiple groups represented by the general formula (11), the multiple groups represented by the general formula (11) may be identical or different from each other. L 1 teeth, A substituted or unsubstituted ring-forming arylene group having 6 to 15 carbon atoms, or A divalent heterocyclic group having 5 to 15 substituted or unsubstituted ring-forming atoms, mx is 1, 2, or 3. L 1 If there are two or more, then there are two or more L 1 They are either identical or different from each other. Ar 1 This is a substituted or unsubstituted aryl group containing four or more rings, Ar 1 If there are two or more Ar 1 They are either identical or different from each other. In the general formula (11) above, * indicates the bond position, In the compound represented by the general formula (1000), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, R 901 If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another. R 801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 (They are either identical or different to each other.)
2. R 10 and R 11 The group, R 11 and R 12 The group, R 12 and R 13 The group, R 13 and R 14 The group, R 14 and R 15 The group, R 16 and R 17 The group, R 17 and R 18 The group, R 18 and R 19 The pair with, and R 19 and R 10 One or more of the groups are They combine with each other to form a substituted or unsubstituted monoring, or They bond to each other to form substituted or unsubstituted fused rings. The compound according to claim 1.
3. R 13 and R 14 The group, R 16 and R 17 The pair with, and R 19 and R 10 Either pair of these elements can bond with each other to form a substituted or unsubstituted benzene ring. The compound according to claim 2.
4. A molecule having at least one group represented by the general formula (11) and containing exactly one benzoxanthene ring represented by the following general formula (1): The compound according to claim 1. 【Chemistry 2】 (In the above general formula (1), R 10 to R 19 each independently has the same meaning as R in the general formula (1000), provided that 10 to R 19 and, provided that R 10 to R 19 any combination of two or more adjacent ones of them are not bonded to each other Ar 1 , L 1 and mx are, respectively, Ar in the general formula (11). 1 , L 1 (And it is synonymous with mx.)
5. A 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 its molecule is represented by the following general formula (121) or general formula (122): The compound according to claim 4. 【Transformation 3】 【Chemistry 4】 (In the above general formulas (121) and (122), R 10 ~R 19 each independently has the same meaning as R in the general formula (1), 10 ~R 19 and is synonymous with, Ar 1 , L 1 and mx are, respectively, Ar in the general formula (11). 1 , L 1 (And it is synonymous with mx.)
6. R is not a group represented by the general formula (11) mentioned above. 10 ~R 19 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, or A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms. The compound according to any one of claims 1 to 5.
7. Ar 1 This is an aryl group formed by the condensation of four or more substituted or unsubstituted benzene rings. The compound according to any one of claims 1 to 6.
8. A compound having at least one group represented by the general formula (11) and containing only one benz[de]anthracene derivative skeleton represented by the general formula (1000) in its molecule is represented by the following general formulas (123), (124), (125), or (126): The compound according to claim 1. 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 (In the above general formulas (123), (124), (125), and (126), X is an oxygen atom, a sulfur atom, C(R) 2001 ) (Caution 2002 ), or Si (R 2003 ) (Caution 2004 ) and R 2001 ~R 2004 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by -N(R) 906 ) (Caution 907 ) a base represented by halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, L 10 teeth, A substituted or unsubstituted ring-forming arylene group having 6 to 15 carbon atoms, or A divalent heterocyclic group having 5 to 15 substituted or unsubstituted ring-forming atoms, Ar 10 This is an aryl group formed by the condensation of four or more substituted or unsubstituted benzene rings. Ar 11 These are substituted or unsubstituted ring-forming aryl groups with 6 to 14 carbon atoms. However, Ar 11 This is not a substituted or unsubstituted anthryl group, m10 is 5, m11 is 6, Rm is independent of each other. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by -N(R) 906 ) (Caution 907 ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by - COOR 802 A base represented by halogen atom, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, Multiple Rm do not combine with each other. R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, R 901 If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another. R 801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 (They are either identical or different to each other.)
9. 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). The compound according to claim 8. 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 (In the above general formulas (1230), (1240), (1250), and (1260), X, L 10 Ar 10 Ar 11 m10, m11, and Rm are each independently L in the general formulas (123), (124), (125), and (126). 10 Ar 10 Ar 11 (This is synonymous with m10, m11, and Rm.)
10. The compound according to claim 8 or claim 9, wherein X is an oxygen atom.
11. A compound having at least one group represented by the following general formula (110A), and containing exactly one benz[de]anthracene derivative skeleton represented by the following general formula (1000A) in its molecule. 【Chemistry 13】 (In the above general formula (1000A), X is an oxygen atom, a sulfur atom, C(R) 2001 ) (Caution 2002 ), or Si (R 2003 ) (Caution 2004 ) and R 2001 ~R 2004 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by -N(R) 906 ) (Caution 907 ) a base represented by halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, R 10 ~R 19 Of these, one or more pairs consisting of two or more adjacent items, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 10 ~R 19 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by -N(R) 906 ) (Caution 907 ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by - COOR 802 A base represented by halogen atom, Nitro group, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, or The group is represented by the general formula (110A) mentioned above, However, R 13 and R 18 At least one of them is a group represented by the general formula (110A), If there are multiple groups represented by the general formula (110A), the multiple groups represented by the general formula (110A) may be the same as or different from each other. L 100 teeth, single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, mx is 1, 2, or 3. L 100 If there are two or more, then there are two or more L 100 They are either identical or different from each other. Ar 1 This is a substituted or unsubstituted aryl group containing four or more rings, Ar 1 If there are two or more Ar 1 They are either identical or different from each other. In the above general formula (110A), * indicates the bonding position. In the compound represented by the general formula (1000A), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, R 901 If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another. R 801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 (They are either identical or different to each other.)
12. R 10 and R 11 The group, R 11 and R 12 The group, R 12 and R 13 The group, R 13 and R 14 The group, R 14 and R 15 The group, R 16 and R 17 The group, R 17 and R 18 The group, R 18 and R 19 The pair with, and R 19 and R 10 One or more of the groups are They combine with each other to form a substituted or unsubstituted monoring, or They bond to each other to form substituted or unsubstituted fused rings. The compound according to claim 11.
13. R 13 and R 14 The group, R 16 and R 17 The pair with, and R 19 and R 10 Either pair of these elements can bond with each other to form a substituted or unsubstituted benzene ring. The compound according to claim 12.
14. A molecule having at least one group represented by the general formula (110A) and containing exactly one benzoxanthene ring represented by the following general formula (100A), The compound according to claim 11. 【Chemistry 14】 (In the above general formula (100A), R 10 ~R 19 Each of these independently corresponds to R in the general formula (1000A) 10 ~R 19 It is synonymous with R 10 ~R 19 Of these, any set consisting of two or more adjacent items does not combine with each other. Ar 1 , L 1 and mx are, respectively, Ar in the general formula (110A). 1 , L 1 (And it is synonymous with mx.)
15. 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 its molecule is represented by the following general formula (121A) or general formula (122A): The compound according to claim 14. 【Chemistry 15】 【Chemistry 16】 (In the above general formulas (121A) and (122A), R 10 ~R 19 Each of these independently corresponds to R in the general formula (100A) 10 ~R 19 It is synonymous with, Ar 1 , L 100 and mx are, respectively, Ar in the general formula (110A). 1 , L 100 (And it is synonymous with mx.)
16. R is not a group represented by the general formula (110A) mentioned above. 10 ~R 19 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, or A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms. The compound according to any one of claims 11 to 15.
17. - (L 1 ) mx A base represented by -, -L 10 A group represented by -, or - (L 100 ) mx The group represented by - is a group represented by any of the following general formulas (111) to (120): The compound according to any one of claims 1 to 16. 【Chemistry 17】 [Chemistry 18] (The asterisks (*) in general formulas (111) to (120) indicate the bonding position.)
18. Ar 1 This is an aryl group formed by the condensation of four or more substituted or unsubstituted benzene rings. The compound according to any one of claims 11 to 17.
19. Ar 1 or Ar 10 This is a group represented by the following general formulas (1100), (1200), (1300), (1400), (1500), (1600), (1700), or (1800): The compound according to any one of claims 1 to 18. 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 (In the above general formula (1100), R 111 ~R 120 One of them is a joint, In the above general formula (1200), R 1201 ~R 1212 One of them is a joint, In the above general formula (1300), R 1301 ~R 1314 One of them is a joint, In the above general formula (1400), R 1401 ~R 1414 One of them is a joint, In the above general formula (1500), R 1501 ~R 1514 One of them is a joint, In the above general formula (1600), R 1601 ~R 1612 One of them is a joint, In the above general formula (1700), R 1701 ~R 1710 One of them is a joint, In the above general formula (1800), R 1801 ~R 1812 One of them is a joint, R is not a joint 111 ~R 120 , not a joint R 1201 ~R 1212 , not a joint R 1301 ~R 1314 , not a joint R 1401 ~R 1414 , not a joint R 1501 ~R 1514 , not a joint R 1601 ~R 1612 , not a joint R 1701 ~R 1710 , and R which is not a joint 1801 ~R 1812 teeth, Each independently, hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by -N(R) 906 ) (Caution 907 ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by - COOR 802 A base represented by halogen atom, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
20. R is not a joint 111 ~R 120 , not a joint R 1201 ~R 1212 , not a joint R 1301 ~R 1314 , not a joint R 1401 ~R 1414 , not a joint R 1501 ~R 1514 , not a joint R 1601 ~R 1612 , not a joint R 1701 ~R 1710 , and R which is not a joint 1801 ~R 1812 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, or A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms. The compound according to claim 19.
21. All bases described as "substitutable or unsubstitutable" are "unsubstitutable" bases. The compound according to any one of claims 1 to 20.
22. Anode and, Cathode and, The system comprises an organic layer disposed between the anode and the cathode, The organic layer includes a light-emitting layer, At least one layer of the organic layer contains the compound described in any one of claims 1 to 21. Organic electroluminescent element.
23. The light-emitting layer contains the compound, The organic electroluminescent element according to claim 22.
24. Anode and, Cathode and, It comprises a light-emitting layer disposed 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 the first compound, The first compound has at least one group represented by the following general formula (110) and is a compound represented by the following general formula (1000B). Organic electroluminescent element. 【Chemistry 23】 (In the above general formula (1000B), X is an oxygen atom, a sulfur atom, C(R) 2001 ) (Caution 2002 ), or Si (R 2003 ) (Caution 2004 ) and R 2001 ~R 2004 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by -N(R) 906 ) (Caution 907 ) a base represented by halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, R 10 ~R 19 Of these, one or more pairs consisting of two or more adjacent items, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 10 ~R 19 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by -N(R) 906 ) (Caution 907 ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by - COOR 802 A base represented by halogen atom, Nitro group, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, or The group is represented by the general formula (110) mentioned above, However, R 10 ~R 19 At least one of them is a group represented by the general formula (110), If there are multiple groups represented by the general formula (110), the multiple groups represented by the general formula (110) may be the same as or different from each other. L 100 teeth, single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, mx is 1, 2, or 3. L 100 If there are two or more, then there are two or more L 100 They are either identical or different from each other. Ar 100 teeth, A substituted or unsubstituted aryl group containing three or more rings, or A substituted or unsubstituted heterocyclic group comprising two or more aromatic rings and one or more heterocyclic rings, Ar 100 It does not contain an anthracene ring, Ar 100 If there are two or more Ar 100 They are either identical or different from each other. In the above general formula (110), * indicates the bond position, In the first compound represented by the general formula (1000B), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, R 901 If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another. R 801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 (They are either identical or different to each other.)
25. R 10 and R 11 The group, R 11 and R 12 The group, R 12 and R 13 The group, R 13 and R 14 The group, R 14 and R 15 The group, R 16 and R 17 The group, R 17 and R 18 The group, R 18 and R 19 The pair with, and R 19 and R 10 One or more of the groups are They combine with each other to form a substituted or unsubstituted monoring, or They bond to each other to form substituted or unsubstituted fused rings. The organic electroluminescent element according to claim 24.
26. R 13 and R 14 The group, R 16 and R 17 The pair with, and R 19 and R 10 Either pair of these elements can bond with each other to form a substituted or unsubstituted benzene ring. The organic electroluminescent element according to claim 25.
27. The first compound has at least one group represented by the general formula (110) and is a compound represented by the following general formula (100). The organic electroluminescent element according to claim 24. 【Chemistry 24】 (In the above general formula (100), R 10 ~R 19 Each of these independently corresponds to R in the general formula (1000B) 10 ~R 19 It is synonymous with R 10 ~R 19 Of these, any set consisting of two or more adjacent items does not combine with each other. Ar 100 , L 100 and mx are, respectively, Ar in the general formula (110). 100 , L 100 (And it is synonymous with mx.)
28. 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. An organic electroluminescent element according to any one of claims 24 to 27.
29. The first light-emitting layer and the second light-emitting layer are in direct contact. An organic electroluminescent element according to any one of claims 24 to 28.
30. The first compound is represented by the following general formula (101) or general formula (102): An organic electroluminescent element according to any one of claims 24 to 29. 【Chemistry 25】 【Chemistry 26】 (In the above general formulas (101) and (102), R 10 ~R 19 Each of these independently corresponds to R in the general formula (1000B) 10 ~R 19 It is synonymous with R 10 ~R 19 Of these, any set consisting of two or more adjacent items does not combine with each other. Ar 100 , L 100 and mx are, respectively, Ar in the general formula (110). 100 , L 100 (And it is synonymous with mx.)
31. R is not a group represented by the general formula (110) mentioned above. 10 ~R 19 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, or A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms. An organic electroluminescent element according to any one of claims 24 to 30.
32. A compound having at least one group represented by the general formula (110) and represented by the general formula (1000B) is represented by the following general formulas (123), (124), (125), or (126): The organic electroluminescent element according to claim 24. 【Chemistry 27】 【Chemistry 28】 【Chemistry 29】 【Transformation 30】 (In the above general formulas (123), (124), (125), and (126), X is an oxygen atom, a sulfur atom, C(R) 2001 ) (Caution 2002 ), or Si (R 2003 ) (Caution 2004 ) and R 2001 ~R 2004 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by -N(R) 906 ) (Caution 907 ) a base represented by halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, L 10 teeth, A substituted or unsubstituted ring-forming arylene group having 6 to 15 carbon atoms, or A divalent heterocyclic group having 5 to 15 substituted or unsubstituted ring-forming atoms, Ar 10 This is an aryl group formed by the condensation of four or more substituted or unsubstituted benzene rings. Ar 11 These are substituted or unsubstituted ring-forming aryl groups with 6 to 14 carbon atoms. However, Ar 11 This is not a substituted or unsubstituted anthryl group, m10 is 5, m11 is 6, Rm is independent of each other. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by -N(R) 906 ) (Caution 907 ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by - COOR 802 A base represented by halogen atom, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, Multiple Rm do not combine with each other. R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, R 901 If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another. R 801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 (They are either identical or different to each other.)
33. 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). The organic electroluminescent element according to claim 32. 【Chemistry 31】 【Chemistry 32】 【Transformation 33】 【Transformation 34】 (In the above general formulas (1230), (1240), (1250), and (1260), X, L 10 Ar 10 Ar 11 m10, m11, and Rm are each independently L in the general formulas (123), (124), (125), and (126). 10 Ar 10 Ar 11 (This is synonymous with m10, m11, and Rm.)
34. The organic electroluminescent element according to claim 32 or claim 33, wherein X is an oxygen atom.
35. Ar 100 This is a group represented by the following general formulas (1100), (1200), (1300), (1400), (1500), (1600), (1700), or (1800): An organic electroluminescent element according to any one of claims 24 to 31. 【Chemistry 35】 【Transformation 36】 【Chemistry 37】 【Transformation 38】 (In the above general formula (1100), R 111 ~R 120 One of them is a joint, In the above general formula (1200), R 1201 ~R 1212 One of them is a joint, In the above general formula (1300), R 1301 ~R 1314 One of them is a joint, In the above general formula (1400), R 1401 ~R 1414 One of them is a joint, In the above general formula (1500), R 1501 ~R 1514 One of them is a joint, In the above general formula (1600), R 1601 ~R 1612 One of them is a joint, In the above general formula (1700), R 1701 ~R 1710 One of them is a joint, In the above general formula (1800), R 1801 ~R 1812 One of them is a joint, R is not a joint 111 ~R 120 , not a joint R 1201 ~R 1212 , not a joint R 1301 ~R 1314 , not a joint R 1401 ~R 1414 , not a joint R 1501 ~R 1514 , not a joint R 1601 ~R 1612 , not a joint R 1701 ~R 1710 , and R which is not a joint 1801 ~R 1812 teeth, Each independently, hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by -N(R) 906 ) (Caution 907 ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by - COOR 802 A base represented by halogen atom, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
36. The second light-emitting layer contains a second compound represented by the following general formula (2): An organic electroluminescent element according to any one of claims 24 to 35. 【Chemistry 39】 (In the above general formula (2), R 201 ~R 208 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by -N(R) 906 ) (Caution 907 ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by - COOR 802 A base represented by halogen atom, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, L 201 and L 202 Each of them operates independently. single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, Ar 201 and Ar 202 Each of them operates independently. A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted. (In the second compound represented by the general formula (2) above, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, R 901 If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another. R 801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 (They are either identical or different to each other.)
37. R 201 ~R 208 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by -N(R) 906 ) (Caution 907 ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by - COOR 802 A base represented by halogen atom, or It is a nitro group, L 201 and L 202 Each of them operates independently. single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, Ar 201 and Ar 202 Each of them operates independently. A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. The organic electroluminescent element according to claim 36.
38. L 201 and L 202 Each of them operates independently. Single bond, or A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, Ar 201 and Ar 202 These are, independently, substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms. The organic electroluminescent element according to claim 36 or claim 37.
39. Ar 201 and Ar 202 Each of them operates independently. Phenyl group, Naphthyl group, Phenanthryl group, biphenyl group, Terphenyl group, diphenylfluorenyl group, Dimethylfluorenyl group, Benzodiphenylfluorenyl group, Benzodimethylfluorenyl group, Dibenzofuranyl group, dibenzothienyl group, Benzoxanthenyl group, Naphthobenzofuranyl group, or It is a naphthobenzothienyl group, An organic electroluminescent element according to any one of claims 36 to 38.
40. The second compound represented by the general formula (2) is a compound represented by the following general formulas (201), (202), (203), (204), (205), (206), (207), (208), or (209). An organic electroluminescent element according to any one of claims 36 to 39. 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 (In the above general formulas (201) to (209), L 201 and Ar 201 L in the general formula (2) is 201 and Ar 201 It is synonymous with, R 201 ~R 208 Each of these independently corresponds to R in the general formula (2) above. 201 ~R 208 (This is synonymous with...)
41. A hole transport layer is provided between the anode and the light-emitting layer. An organic electroluminescent element according to any one of claims 24 to 40.
42. An electron transport layer is provided between the cathode and the light-emitting layer. An organic electroluminescent element according to any one of claims 24 to 41.
43. The first light-emitting layer further contains a third fluorescent compound, The third compound is a compound that exhibits emission with a main peak wavelength of 430 nm or more and 480 nm or less. An organic electroluminescent element according to any one of claims 24 to 42.
44. The second light-emitting layer further contains a fluorescent fourth compound, The fourth compound is a compound that exhibits emission with a main peak wavelength of 430 nm or more and 480 nm or less. An organic electroluminescent element according to any one of claims 24 to 43.
45. An electronic device equipped with an organic electroluminescent element according to any one of claims 22 to 44.