Organic electroluminescent elements and electronic devices
The use of specific compounds in the anode, cathode, and intermediate layers of organic electroluminescent elements addresses leakage current issues, enhancing the lifespan and reliability of electronic devices.
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- IDEMITSU KOSAN CO LTD
- Filing Date
- 2024-12-23
- Publication Date
- 2026-07-03
AI Technical Summary
Electronic devices equipped with multiple organic electroluminescent elements experience leakage current, leading to pixel defects.
An organic electroluminescent element design incorporating specific compounds in the anode, cathode, light-emitting layers, and charge generation/transport layers, including a first host material with deuterium atoms, to suppress leakage current and enhance lifespan.
The solution effectively reduces leakage current and extends the lifespan of the organic electroluminescent elements, improving the performance and reliability of electronic devices.
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Figure 2026111279000001_ABST
Abstract
Description
[Technical Field]
[0001] This invention relates to 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%. Examples of performance characteristics of organic EL elements include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan. For example, Patent Documents 1 and 2 describe studies aimed at improving the performance of organic EL elements. [Prior art documents] [Patent Documents]
[0003] [Patent Document 1] Chinese Patent Application Publication No. 116496308 Specification [Patent Document 2] Chinese Patent Application Publication No. 117088920 Specification [Overview of the Initiative] [Problems that the invention aims to solve]
[0004] In electronic devices equipped with multiple organic electroluminescent elements, leakage current can occur between these elements, potentially leading to pixel defects.
[0005] The object of the present invention is to provide an organic electroluminescent element that suppresses the generation of leakage current and has a long lifespan, and to provide an electronic device equipped with the organic electroluminescent element. [Means for solving the problem]
[0006] According to one aspect of the present invention, Anode and, Cathode and, One or more light-emitting bands arranged between the anode and the cathode, It has one or more charge generation and transport bands arranged between the anode and the cathode, Each of the above-mentioned light emission bands independently includes one or more light emission layers. Of the one or more light emission bands, at least one includes the first light emission layer. The first light-emitting layer contains a compound represented by the following formula (2) as a first host material, and the first host material has at least one deuterium atom. Each of the one or more charge generation and transport bands independently includes at least one band selected from the group consisting of charge generation bands and charge transport bands. Of the one or more charge generation and transport bands, at least one includes the first organic layer. The first organic layer contains a compound represented by the following formula (AC1): An organic electroluminescent element is provided.
[0007] [ka]
[0008] (In the above formula (AC1), R 11 , R 12 , R 13 and R 14 Each of these is independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, or a nitro group. X 11 is a nitrogen atom or C(Q11 ) and X 12 is a nitrogen atom or C(Q 12 ) and X 13 is a nitrogen atom or C(Q 13 ) and X 14 is a nitrogen atom or C(Q 14 ) and X 15 is a nitrogen atom or C(Q 15 ) and X 16 is a nitrogen atom or C(Q 16 ) and Q 11 , Q 12 , Q 13 , Q 14 , Q 15 , and Q 16 is each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, or a nitro group.) (In the formula (2), R 201 ~R 208 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl 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 substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 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 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. (In the compound represented by 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 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 902They 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.
[0009] According to one aspect of the present invention, an electronic device is provided that incorporates an organic electroluminescent element according to one aspect of the present invention. [Effects of the Invention]
[0010] According to one aspect of the present invention, it is possible to provide an organic electroluminescent element that suppresses the generation of leakage current and has a long lifespan. Furthermore, according to one aspect of the present invention, it is possible to provide an electronic device equipped with an organic electroluminescent element according to one aspect of the present invention. [Brief explanation of the drawing]
[0011] [Figure 1] This figure shows a schematic configuration of a first example of an organic EL element according to the first embodiment. [Figure 2] This figure shows a schematic configuration of a second example of an organic EL element according to the first embodiment. [Figure 3] This figure shows a schematic configuration of a third example of an organic EL element according to the first embodiment. [Figure 4] This figure shows a schematic configuration of a fourth example of an organic EL element according to the first embodiment. [Figure 5] This is a schematic plan view showing a substrate with comb-tooth electrodes used as an element for measuring sheet resistance. [Figure 6] This is a schematic cross-sectional view of an element used for measuring sheet resistance. [Modes for carrying out the invention]
[0012] [Definition] In this specification, the term "hydrogen atom" includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.
[0013] 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.
[0014] 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.
[0015] 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.
[0016] 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.
[0017] 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.
[0018] 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.
[0019] "Substituents as described herein" The substituents described herein will be explained below.
[0020] 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.
[0021] • "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.
[0022] • 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).
[0023] [ka]
[0024] [ka]
[0025] • 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.
[0026] • "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.
[0027] 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).
[0028] 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).
[0029] • 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.
[0030] • 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.
[0031] • 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).
[0032] • 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):
[0033] [ka]
[0034] [ka]
[0035] 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.
[0036] • 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.
[0037] • 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].
[0038] • 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].
[0039] • 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):
[0040] 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 A This refers to one or more hydrogen atoms selected from the hydrogen atoms of the methylene group when one of the atoms is CH2.
[0041] • "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.
[0042] • 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.
[0043] • Substituting alkyl groups (specific examples group G3B): Heptafluoropropyl group (including isomers), Pentafluoroethyl group, 2,2,2-trifluoroethyl group, and Trifluoromethyl group.
[0044] • "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.
[0045] • Unsubstituted alkenyl groups (specific examples group G4A): vinyl group, allyl group, 1-Butenyl group, 2-butenyl group, and 3-Butenyl group.
[0046] • 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.
[0047] • "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.
[0048] • Unsubstituted alkynyl groups (specific examples group G5A): Ethynyl group
[0049] • "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.
[0050] • 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.
[0051] • Substituting cycloalkyl groups (specific examples group G6B): 4-methylcyclohexyl group.
[0052] · "-Si(R 901 )(R 902 )(R 903 ) a base represented by -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.
[0053] ·「-O-(R 904 ) a base represented by The following information pertains to the -O-(R 904 ) 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.
[0054] · "-S-(R 905 ) a base represented by 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.
[0055] · "-N(R 906 )(R 907 ) a base represented by -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), -N(G3)(G3), and -N(G6)(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. 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), the multiple G6s are either identical or different from one another.
[0056] • "Halogen atom" Specific examples of "halogen atoms" as described herein (Specific Examples Group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.
[0057] • "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.
[0058] • "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.
[0059] • "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.
[0060] • "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.
[0061] • "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.
[0062] • "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.
[0063] • "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.
[0064] • "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.
[0065] 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.
[0066] 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.
[0067] In this specification, unless otherwise specified, the carbazolyl group is specifically one of the following groups:
[0068] [ka]
[0069] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically one of the following groups:
[0070] [ka]
[0071] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bond position.
[0072] In this specification, unless otherwise specified, the dibenzofuranyl group and the dibenzothiophenyl group specifically refer to any of the following groups:
[0073] [ka]
[0074] In the general formulas (TEMP-34) to (TEMP-41) above, * represents a bond position.
[0075] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and t-butyl groups.
[0076] • "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.
[0077] • "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.
[0078] · "Substituted or unsubstituted alkylene group" Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group". Specific examples (specific example group G14) of the "substituted or unsubstituted alkylene group" include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3 and the like.
[0079] Unless otherwise specified in this specification, the substituted or unsubstituted arylene group described in this specification is preferably a group of any of the following general formulas (TEMP-42) to (TEMP-68).
[0080]
Chemical formula
[0081]
Chemical formula
[0082] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 are each independently a hydrogen atom or a substituent. In the above general formulas (TEMP-42) to (TEMP-52), * represents the bonding position.
[0083]
Chemical formula
[0084] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent. Formula Q9 and Q 10 may be bonded to each other via a single bond to form a ring. In the general formulas (TEMP-53) to (TEMP-62) above, * represents a bond position.
[0085] [ka]
[0086] 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.
[0087] 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).
[0088] [ka]
[0089] [ka]
[0090] [ka]
[0091] In the general formulas (TEMP-69) to (TEMP-82) above, Q1 to Q9 are each independently a hydrogen atom or a substituent.
[0092] [ka]
[0093] [ka]
[0094] [ka]
[0095] [ka]
[0096] In the general formulas (TEMP-83) to (TEMP-102) above, Q1 to Q8 are each independently a hydrogen atom or a substituent.
[0097] The above is a description of the substituents described herein.
[0098] • "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.
[0099] [ka]
[0100] For example, R921 ~R 930 Among the cases where "one or more of the pairs consisting of two or more adjacent ones are combined with each other to form a ring", the pair consisting of two adjacent ones that forms one pair is R 921 and R 922 and the pair of R 922 and R 923 and the pair of R 923 and R 924 and the pair of R 924 and R 930 and the pair of R 930 and R 925 and the pair of R 925 and R 926 and the pair of R 926 and R 927 and the pair of R 927 and R 928 and the pair of R 928 and R 929 and the pair of, and R 929 and R 921 and the pair of.
[0101] The above "one or more" means that two or more of the pairs consisting of two or more adjacent ones may form a ring at the same time. For example, R 921 and R 922 are combined with each other to form a ring Q A , and at the same time R 925 and R 926 are combined with each other to form a ring Q B is formed, then the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).
[0102]
Chemical formula
[0103] The case where a "pair consisting of two or more adjacent ones" forms a ring includes not only the case where a pair consisting of "two" adjacent ones is combined as in the above example, but also the case where a pair consisting of "three or more" adjacent ones is combined. For example, R 921 and R 922 are combined with each other to form a ring Q A , and 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.
[0104] [ka]
[0105] 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.
[0106] 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.
[0107] 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 monoring or a fused 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.
[0108] 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").
[0109] • 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 Unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms It is a base selected from the group consisting of, 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, 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 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. R903 If there are two or more of them, then there are two or more R 903 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.
[0110] 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 Heterocyclic groups with 5 to 50 ring-forming atoms It is a group selected from the group consisting of the following.
[0111] 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 Heterocyclic groups with 5 to 18 ring-forming atoms It is a group selected from the group consisting of the following.
[0112] Specific examples of each of the above-mentioned substituents are the specific examples of substituents described in the section "Substituents as described herein" above.
[0113] 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.
[0114] 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.
[0115] [First Embodiment] The organic electroluminescent element according to this embodiment includes an anode, a cathode, one or more light-emitting bands disposed between the anode and the cathode, and one or more charge-generating transport bands disposed between the anode and the cathode. Each of the one or more emission bands independently includes one or more emission layers, and at least one of the one or more emission bands includes a first emission layer, the first emission layer contains a compound represented by the following formula (2) as a first host material, and the first host material has at least one deuterium atom. Each of the one or more charge generation and transport bands independently includes at least one band selected from the group consisting of charge generation bands and charge transport bands, and at least one of the one or more charge generation and transport bands includes a first organic layer, the first organic layer contains a compound represented by the following formula (AC1).
[0116] In the organic EL element according to this embodiment, the compound represented by formula (AC1) contained in the first organic layer has a high sheet resistance and has the effect of suppressing leakage current generated between multiple pixels. This effect is due to the weak acceptor properties of the compound represented by formula (AC1). On the other hand, the compound represented by formula (AC1) has poor acceptor properties, which leads to the problem of low hole injection into the light-emitting layer. When hole injection into the light-emitting layer is low, the amount of electrons injected into the light-emitting layer increases relatively more than the amount of holes injected into the light-emitting layer, increasing the electronic load on the interface between the electron barrier layer and the light-emitting layer, and as a result, the device lifetime decreases. Therefore, in the organic EL element according to this embodiment, by incorporating a compound represented by formula (AC1) in the first organic layer (for example, the hole injection layer) and a deuterated, highly durable first host material (a compound represented by formula (2)) in the first light-emitting layer, appropriate light-emitting lifetime characteristics can be obtained even in elements where a large load is applied to the interface between the electron barrier layer and the first light-emitting layer. Therefore, according to this embodiment, it is possible to suppress the generation of leakage current and realize an organic EL element with a long lifespan.
[0117] <Compound represented by formula (AC1)> The compound represented by formula (AC1) has at least one charge generation transport band containing a first organic layer, and the first organic layer contains the compound represented by formula (AC1). In this specification, the compound represented by formula (AC1) may be referred to as the first acceptor material.
[0118] [ka]
[0119] (In the above formula (AC1), R 11 , R 12 , R 13 and R 14 Each of these is independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, or a nitro group. X 11 is a nitrogen atom or C(Q 11 ) and X 12 is a nitrogen atom or C(Q 12 ) and X 13is a nitrogen atom or C(Q 13 ) and X 14 is a nitrogen atom or C(Q 14 ) and X 15 is a nitrogen atom or C(Q 15 ) and X 16 is a nitrogen atom or C(Q 16 ) and Q 11 Q 12 Q 13 Q 14 Q 15 , and Q 16 These are, independently, a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, or a nitro group.
[0120] In the organic EL element according to this embodiment, R in the first acceptor material 11 , R 12 , R 13 and R 14 Preferably, each of these is independently a cyano group or a nitro group.
[0121] In the organic EL element according to this embodiment, R in the first acceptor material 11 , R 12 , R 13 and R 14 It is preferable that the group is a cyano group.
[0122] In the organic EL element according to this embodiment, the first acceptor material (compound represented by formula (AC1)) is preferably a compound represented by the following formula (AC2).
[0123] [ka]
[0124] (In the above formula (AC2), X 11 , X 12 , X 13 , X 14 , X 15, and X 16 These are, respectively, X in the above formula (AC1). 11 , X 12 , X 13 , X 14 , X 15 , and X 16 (This is synonymous with...)
[0125] In the organic EL element according to this embodiment, X in the first acceptor material 11 C(Q) 11 ) and X 12 C(Q) 12 ) and X 13 C(Q) 13 ) and X 14 C(Q) 14 ) and X 15 C(Q) 15 ) and X 16 C(Q) 16 ) is preferable.
[0126] In the organic EL element according to this embodiment, the first acceptor material (compound represented by formula (AC1)) is preferably a compound represented by the following formula (AC3).
[0127] [ka]
[0128] (In the above formula (AC3), R 11 , R 12 , R 13 , R 14 Q 11 Q 12 Q 13 Q 14 Q 15 , and Q 16 These are, respectively, R in the above formula (AC1). 11 , R 12 , R 13 , R 14 Q 11 Q 12 Q 13 Q 14 Q 15, and Q 16 (This is synonymous with...)
[0129] In the organic EL element according to this embodiment, the first acceptor material (compound represented by formula (AC1)) is preferably a compound represented by the following formula (AC4).
[0130] [ka]
[0131] (In the above formula (AC4), Q 11 Q 12 Q 13 Q 14 Q 15 , and Q 16 These are, respectively, Q in the above formula (AC1). 11 Q 12 Q 13 Q 14 Q 15 , and Q 16 (This is synonymous with...)
[0132] In the organic EL element according to this embodiment, Q in the first acceptor material 11 Q 12 Q 13 Q 14 Q 15 , and Q 16 Each of these is preferably independently a hydrogen atom, a fluorine atom, or a cyano group.
[0133] In the organic EL element according to this embodiment, Q in the first acceptor material 11 Q 12 Q 13 Q 14 Q 15 , and Q 16 Preferably, each of these is independently a fluorine atom or a cyano group.
[0134] In the organic EL element according to this embodiment, Q in the first acceptor material 11 Q 12 Q13 Q 14 Q 15 , and Q 16 Preferably, it is a fluorine atom.
[0135] (Method for producing the compound represented by formula (AC1)) The compound represented by formula (AC1) (first acceptor material) can be produced by known methods. Furthermore, the compound represented by formula (AC1) can also be produced by following known methods and using known alternative reactions and starting materials tailored to the target product.
[0136] (Specific examples of compounds represented by formula (AC1)) Specific examples of compounds represented by formula (AC1) include the following compounds. However, the present invention is not limited to these specific examples.
[0137] [ka]
[0138] [Organic EL element configuration] The organic EL element according to this embodiment includes an anode, a cathode, one or more light-emitting bands disposed between the anode and the cathode, and one or more charge-generating transport bands disposed between the anode and the cathode.
[0139] <Light-emitting unit> The organic EL element according to this embodiment preferably has at least one light-emitting unit contained between the anode and the cathode. The light-emitting unit comprises one or more layers, and preferably at least one of the layers comprising the light-emitting unit is a light-emitting layer. In addition to the light-emitting layer, the light-emitting unit may have one or more layers containing at least one selected from the group consisting of organic compounds and inorganic substances. Inorganic substances are at least one of inorganic compounds and elemental substances. The light-emitting unit preferably comprises one or more layers selected from the group consisting of layers composed of organic compounds, layers composed of inorganic substances, and layers composed of both organic compounds and inorganic substances. Examples of layers that may be included in the light-emitting unit other than the light-emitting layer include layers that can be used in organic EL elements. There are no particular limitations on layers that can be used in organic EL elements, but examples include at least one layer selected from the group consisting of hole injection layers, hole transport layers, electron injection layers, electron transport layers, and barrier layers. Examples of barrier layers include hole barrier layers and electron barrier layers. Furthermore, the light-emitting unit may include a light-emitting band containing a light-emitting layer, a hole transport band positioned between the light-emitting band and the anode, and an electron transport band positioned between the light-emitting band and the cathode. Each band independently includes one or more layers.
[0140] In the organic EL element according to this embodiment, it is preferable that each light-emitting unit includes one light-emitting band. Each light-emitting band may independently include only one light-emitting layer, or it may include two or more light-emitting layers.
[0141] In the organic EL element according to this embodiment, it is preferable that each light-emitting layer included in each light-emitting band independently contains a host material and a light-emitting compound. In the organic EL element according to this embodiment, each light-emitting compound contained in each light-emitting layer is independently either fluorescent or phosphorescent. In the organic EL element according to this embodiment, it is preferable that at least one of the light-emitting layers contains a fluorescent light-emitting compound.
[0142] <Charge generation and transport band> In the organic EL element according to this embodiment, the light-emitting unit may include a light-emitting band and one or more charge generation and transport bands. Each of the one or more charge generation and transport bands independently includes either a charge generation band or a charge transport band.
[0143] <Charge transport band> In the organic EL element according to this embodiment, the light-emitting unit preferably includes a light-emitting band and a charge transport band. Examples of the charge transport band include a hole transport band or an electron transport band. In this embodiment, it is preferable that the organic EL element includes at least one charge generation and transport band selected from the group consisting of hole transport bands and electron transport bands.
[0144] (Hole transport band) The hole transport band is located on the anode side of the emission band. In the organic EL element according to this embodiment, it is preferable that at least one of the one or more charge generation and transport bands includes a hole transport band as a charge transport band. It is preferable that the hole transport band is located between the light emission band closest to the anode and the anode, among the one or more light emission bands.
[0145] In the organic EL element according to this embodiment, the hole transport band preferably includes a first organic layer containing a compound represented by formula (AC1). The layer containing the compound represented by formula (AC1) may be referred to as the first acceptor material-containing layer (first organic layer). The first acceptor material is preferably contained in the hole transport band closest to the anode, and more preferably in the organic layer closest to the anode. The inclusion of a compound whose hole transport band is represented by formula (AC1) suppresses the degradation of device performance and increases the sheet resistance between multiple organic EL elements, thereby suppressing the generation of leakage current.
[0146] In the organic EL element according to this embodiment, it is preferable that the one or more organic layers included in the hole transport band are two or more organic layers. It is preferable that at least one selected from the group consisting of two or more organic layers included in the hole transport band is a first acceptor material-containing layer.
[0147] In one embodiment of the organic EL element according to this embodiment, the hole transport band includes a hole injection layer and a hole transport layer. In one embodiment of the organic EL element according to this embodiment, when the hole transport band consists of two organic layers, a hole injection layer and a hole transport layer, the hole injection layer is the first acceptor material containing layer (first organic layer). In one embodiment of the organic EL element according to this embodiment, the hole transport layer is in direct contact with the light-emitting layer in the light-emitting band.
[0148] In the organic EL element according to this embodiment, it is also preferable that the one or more organic layers included in the hole transport band be three or more organic layers. It is also preferable that at least one selected from the group consisting of three or more organic layers included in the hole transport band is a first acceptor material-containing layer.
[0149] In one embodiment of the organic EL element according to this embodiment, the hole transport band includes a hole injection layer, a hole transport layer, and an electron barrier layer. In one embodiment of the organic EL element according to this embodiment, when the hole transport band consists of three organic layers—a hole injection layer, a hole transport layer, and an electron barrier layer—the hole injection layer is the first acceptor material-containing layer. In one embodiment of the organic EL element according to this embodiment, it is preferable that the electron barrier layer is in direct contact with the light-emitting layer in the light-emitting band.
[0150] In one embodiment of the organic EL element of this embodiment, the organic layer located furthest to the anode among the organic layers containing the hole transport band is the first acceptor material-containing layer.
[0151] In one embodiment of the organic EL element according to this embodiment, the organic layer in direct contact with the anode among the organic layers containing the hole transport band is the first acceptor material-containing layer.
[0152] In one embodiment of the organic EL device according to this embodiment, the hole transport band may independently include two or more electron barrier layers having at least one of the thickness and composition of each layer different from each other, or it may include two or more hole transport layers having at least one of the thickness and composition of each layer different from each other. For example, the hole transport band may include a first electron barrier layer and a second electron barrier layer, in order from the anode side, where at least one of the thickness and composition of the layers differs from each other. Furthermore, for example, the hole transport band may include a first hole transport layer and a second hole transport layer, in order from the anode side, where at least one of the thickness and composition of the layers differs from each other.
[0153] In the organic EL element according to this embodiment, it is preferable that each of the layers in the hole transport band (for example, the hole injection layer, the hole transport layer, the first hole transport layer, the second hole transport layer, the electron barrier layer, the first electron barrier layer, and the second electron barrier layer) independently contains a hole transport band material. It is more preferable that the hole injection layer contains the compound represented by formula (AC1) and the hole transport band material. It is preferable that the hole transport band material contained in the hole injection layer and the hole transport band material contained in the hole transport layer are the same compound. The hole transport band materials contained in the hole injection layer and the hole transport layer may be different compounds.
[0154] In the organic EL element according to this embodiment, if at least one charge generation band contains a compound represented by formula (AC1) (first acceptor material), the hole transport band does not necessarily have to contain the first acceptor material, but it is preferable that it contains the first acceptor material. If the hole transport band does not contain the first acceptor material, it is preferable that the hole transport band contains a second acceptor material. The second acceptor material is a compound different from the first acceptor material, and the second acceptor material will be described later.
[0155] In the organic EL element according to this embodiment, it is also preferable that the content of the first acceptor material in the first acceptor material-containing layer be less than 50% by mass, 40% by mass or less, 30% by mass or less, or 20% by mass or less. In the organic EL element according to this embodiment, it is also preferable that the content of the first acceptor material in the first acceptor material-containing layer be 0.5% by mass or more, 1% by mass or more, 3% by mass or more, 5% by mass or more, or 10% by mass or more. In the organic EL element according to this embodiment, if the first acceptor material-containing layer contains a hole transport band material and the first acceptor material, it is also preferable that the content of the hole transport band material in the first acceptor material-containing layer is more than 50% by mass, 60% by mass or more, 70% by mass or more, or 80% by mass or more. In the organic EL element according to this embodiment, the content of the hole transport band material in the first acceptor material-containing layer is preferably 99.5% by mass or less, 99% by mass or less, 97% by mass or less, 95% by mass or less, or 90% by mass or less. The total content of the first acceptor material and the hole transport band material in the first acceptor material-containing layer is preferably 100% by mass or less.
[0156] In the organic EL element according to this embodiment, it is also preferable that both the charge generation band and the hole transport band contain the compound represented by formula (AC1) (first acceptor material). The first acceptor material contained in the charge generation band and the first acceptor material contained in the hole transport band may be the same compound or different compounds.
[0157] (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. 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), 1, Aromatic amine compounds such as 3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (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. 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.
[0158] In the organic EL element according to this embodiment, the hole injection layer may also preferably contain a hole transport band material and an acceptor material. The acceptor material is preferably a first acceptor material (a compound represented by formula (AC1)) or a second acceptor material. The second acceptor material will be described later.
[0159] (Hole transport layer) The hole transport layer is a layer containing a substance with high hole transport capabilities. In the organic EL element according to this embodiment, the hole transport layer may contain a compound different from the hole transport band material described above, for example, one or more compounds selected from the group consisting of aromatic amine compounds, carbazole derivatives, and anthracene derivatives. Specifically, the hole transport layer may contain 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-phenylamine Aromatic amine compounds such as [no]biphenyl (abbreviation: DFLDPBi), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: 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. The hole transport layer may use carbazole derivatives such as CBP, CzPA, and PCzPA, or anthracene derivatives such as t-BuDNA, DNA, and DPAnth. Alternatively, polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) or poly(4-vinyltriphenylamine) (abbreviated as PVTPA) can also be used in the hole transport layer. However, other materials may be used as the hole transport layer, as long as they have higher hole transport capabilities than electron transport. The layer containing the material with high hole transport capabilities may be a single layer or a layer in which two or more layers made of the above material are stacked. In the organic EL element according to this embodiment, the hole transport band may include one hole transport layer or two or more hole transport layers. Other hole transport band materials will be discussed later.
[0160] (Electron barrier layer) The electron barrier layer is preferably a layer that transports holes and prevents electrons from reaching the layer on the anode side of the electron barrier layer (for example, the hole transport layer). In the organic EL element according to this embodiment, it is also preferable that the compounds contained in the electron barrier layer are, independently, hole transport band materials. In the organic EL element according to this embodiment, it is also preferable that the compounds contained in the electron barrier layer are, independently, compounds represented by formula (B1) or formula (B100), as described later. In the organic EL element according to this embodiment, the compounds contained in the electron barrier layer are, independently, compounds used in known electron barrier layers, and are preferably at least one compound selected from the group consisting of aromatic amine compounds and carbazole derivatives. Furthermore, the compounds contained in the electron barrier layer may independently be monoamine compounds having only one substituted or unsubstituted amino group in the molecule. Also, the compounds contained in the electron barrier layer may independently have a substituted or unsubstituted carbazolyl group and one substituted or unsubstituted amino group in the molecule. The electron barrier layer may be a layer that prevents excitons generated in the light-emitting layer from moving to layers on the anode side of the electron barrier layer (for example, hole transport layers and hole injection layers) so that excitation energy does not leak from the light-emitting layer to the surrounding layers.
[0161] (Electron transport band) In the organic EL element according to this embodiment, the electron transport band includes one or more layers. The electron transport band is preferably located between the cathode and the light-emitting band. The electron transport band located between the light-emitting band and the cathode is preferably in direct contact with the cathode.
[0162] In the organic EL element according to this embodiment, the electron transport band preferably includes at least one selected from the group consisting of a hole barrier layer, an electron transport layer, and an electron injection layer.
[0163] In the organic EL element according to this embodiment, the electron transport band may include two or more layers. Preferably, the electron transport band includes a hole barrier layer and an electron transport layer in that order from the anode side. In this case, it is also preferable that the hole barrier layer is in direct contact with the light-emitting layer in the light-emitting band. Furthermore, it is preferable that the electron transport band includes an electron transport layer and an electron injection layer, in that order from the anode side. In this case, it is also preferable that the electron transport layer is in direct contact with the light-emitting layer in the light-emitting band.
[0164] In the organic EL element according to this embodiment, the electron transport band may include three or more layers. It is also preferable that the electron transport band includes three layers in order from the anode side: a hole barrier layer, an electron transport layer, and an electron injection layer. In this case, it is also preferable that the hole barrier layer is in direct contact with the light-emitting layer in the light-emitting band.
[0165] In the organic EL element according to this embodiment, it is preferable that each layer in the electron transport band (for example, a hole barrier layer, an electron transport layer, and an electron injection layer) independently contains an electron transport band material.
[0166] (Metals and metallic compounds) In one embodiment of the organic EL element according to this embodiment, the layer included in the electron transport band may contain at least one selected from the group consisting of metals and metal compounds. In one embodiment of the organic EL element according to this embodiment, the layer included in the electron transport band may contain at least one selected from the group consisting of metals and metal compounds, and an electron transport band material. The metal that may be included in the electron transport band is, for example, at least one metal selected from the group consisting of rare earth metals, alkali metals, and alkaline earth metals. The metal that may be included in the electron transport band is, for example, at least one metal selected from the group consisting of ytterbium, erbium, lithium, cesium, magnesium, and calcium. The metal compound that may be included in the electron transport band is, for example, at least one metal compound selected from the group consisting of alkali metal compounds and alkaline earth metal compounds. The electron transport band may contain, for example, at least one metal compound selected from the group consisting of 8-(quinolinolato)lithium (abbreviated as Liq), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), 2-(2-pyridyl)phenolate (abbreviated as LiPP), 2-(2-pyridyl)-3-pyridinolatritium (abbreviated as LiPPy), 4-phenyl-2-(2-pyridyl)phenolate (abbreviated as LiPPP), lithium oxide (LiOx), and cesium carbonate.
[0167] (Hole barrier layer) The hole barrier layer is preferably a layer that transports electrons and prevents holes from reaching the cathode-side layer (e.g., the electron transport layer). The compound contained in the hole barrier layer is, for example, a compound used in known hole barrier layers. The compound contained in the hole barrier layer is preferably, for example, an electron transport band material. It is also preferable that the compound contained in the hole barrier layer is at least one compound selected from the group consisting of metal complexes, heteroaromatic compounds, and polymer compounds, similar to the compounds that can be used in the electron transport layer described later. Furthermore, the compound contained in the hole barrier layer may be at least one compound selected from the group consisting of imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives. In the organic EL element according to this embodiment, the electron transport band material contained in the hole barrier layer is preferably a diazine derivative or a triazine derivative, and more preferably a pyrimidine derivative or a 1,3,5-triazine derivative. The hole barrier layer is also preferably a layer that prevents excitons generated in the light-emitting layer from moving to layers on the cathode side of the hole barrier layer (for example, electron transport layers and electron injection layers) so that excitation energy does not leak from the light-emitting layer to the surrounding layers.
[0168] (electron transport layer) In the organic EL element according to this embodiment, it is preferable to include an electron transport layer between the cathode and one or more light-emitting layers that are close to the cathode and that are included in the light-emitting band. The electron transport layer is a layer containing a material with high electron transport properties. The aforementioned electron transport band materials can be used in the electron transport layer. In addition, the electron transport layer can also use 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, as low molecular weight organic compounds, metal complexes 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 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 (abbreviated 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. The substances described here 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. 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. In the organic EL element according to this embodiment, the electron transport layer preferably contains an azine derivative as an electron transport band material. In the organic EL element according to this embodiment, the electron transport band material is preferably a diazine derivative or a triazine derivative, and more preferably a pyrimidine derivative or a 1,3,5-triazine derivative. Other electron transport band materials will be discussed later.
[0169] (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, rare earth metals, or compounds thereof, such as lithium (Li), cesium (Cs), calcium (Ca), ytterbium (Yb), erbium (Er), 8-(quinolinolato)lithium (Liq), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiOx). Alternatively, a material containing alkali metals, alkaline earth metals, rare earth metals, or compounds thereof in an electron-transporting material, specifically one containing magnesium (Mg) in Alq, may be used. In this case, electron injection from the cathode can be performed more efficiently. Alternatively, a composite material obtained 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 in transporting the generated electrons. Specifically, for example, the electron transport band material or the material mentioned in the description of the electron transport layer described above 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.
[0170] <Emission Band> In the organic EL element according to this embodiment, it is preferable that each light-emitting layer containing one or more light-emitting bands contains a host material and a light-emitting compound. The host material may also be referred to as a matrix material. The light-emitting compound may also be referred to as a dopant material, guest material, emitter, or light-emitting material. In the organic EL element according to this embodiment, the luminescent compound contained in each light-emitting layer is independently either fluorescent or phosphorescent. In the organic EL element of this embodiment, it is preferable that one or more light-emitting layers include one or more light-emitting layers containing a light-emitting compound having fluorescence properties. In the organic EL element of this embodiment, at least one of the one or more light-emitting bands includes a first light-emitting layer. Each of the one or more light-emitting bands may independently include only one light-emitting layer or two or more light-emitting layers. In the organic EL element according to this embodiment, it is preferable that the light-emitting band closest to the anode includes the first light-emitting layer between the anode and the cathode.
[0171] In the organic EL element according to this embodiment, it is preferable that a first organic layer containing a compound represented by formula (AC1) is arranged between the anode and the light-emitting band closest to the anode. In the organic EL element according to this embodiment, it is preferable that a first organic layer containing a compound represented by formula (AC1) is disposed between the anode and the first light-emitting layer.
[0172] (First light-emitting layer) In the organic EL element according to this embodiment, the first light-emitting layer includes a first host material. The first host material is a compound represented by formula (2) and has at least one deuterium atom. In one embodiment of the organic EL element according to this embodiment, the first light-emitting layer includes the first host material and a first light-emitting compound. 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 host material in an amount of 50% by mass or more of the total mass of the first light-emitting layer. 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. If the light-emitting layer contains a host material and a light-emitting compound, the upper limit of the total content of the host material and the light-emitting compound is 100% by mass.
[0173] (Compound represented by formula (2) (first host material))
[0174] [ka]
[0175] (In the above 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, 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 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. (In the compound represented by formula (2) above, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802Each 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.
[0176] In one embodiment of the organic EL element according to this embodiment, Ar in formula (2) 201 and Ar 202 At least one of them is a group represented by the following formula (HY1). In one embodiment of the organic EL element according to this embodiment, Ar in formula (2) 201 and Ar 202 One of them is the group represented by the following formula (HY1). In one embodiment of the organic EL element according to this embodiment, Ar in formula (2) 201 and Ar 202 However, each of these groups is independently represented by the following formula (HY1).
[0177] [ka]
[0178] (In the above formula (HY1), R Y1 ~R Y8 and R Y11 ~R Y14 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 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. ny is either 0 or 1. however, When ny is 0, R Y1 ~R Y8 One of the selected options is a single bond that joins *ey, When ny is 1, one condition is satisfied which is selected from the group consisting of (a1) to (a3) below, and R Y5 ~R Y8 , R Y11 ~R Y14 , as well as R which is not a single bond attached to *cy and *dy Y1 ~R Y4 One of the groups selected is a single bond that connects to *ey. (a1)R Y1 and R Y2 One of them is a single bond that connects to *cy, and R Y1 and R Y2 The other bond is a single bond that connects to *dy. (a2)R Y2 and R Y3 One of them is a single bond that connects to *cy, and R Y2 and R Y3 The other bond is a single bond that connects to *dy. (a3)R Y3 and R Y4 One of them is a single bond that connects to *cy, and R Y3 and R Y4 The other bond is a single bond that connects to *dy. Z2 is either an oxygen atom or a sulfur atom. *fy is L in the host material. 201 or L 202 (This indicates the bonding position.)
[0179] In one embodiment of the organic EL element according to this embodiment, Ar in formula (2) 201 and Ar 202 At least one of them is a group selected from the group consisting of groups represented by the following formulas (HY11), (HY12), and (HY13). In one embodiment of the organic EL element according to this embodiment, Ar in formula (2) 201 and Ar 202One of the groups is selected from the group consisting of groups represented by the following formulas (HY11), (HY12), and (HY13). In one embodiment of the organic EL element according to this embodiment, Ar in formula (2) 201 and Ar 202 However, each of these groups is independently selected from the group consisting of groups represented by the following formulas (HY11), (HY12), and (HY13).
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[0183] (In the above formulas (HY11), (HY12), and (HY13), R Y1 ~R Y8 , R Y11 ~R Y14 , and Z2 are, respectively, R in formula (HY1). Y1 ~R Y8 , R Y11 ~R Y14 , and is synonymous with Z2, However, R Y1 ~R Y8 and R Y11 ~R Y14 Of these, one is a single bond that connects to *ey, *fy is L in the host material. 201 or L 202 (This indicates the bonding position.)
[0184] In one embodiment of the organic EL element of this embodiment, Z2 is an oxygen atom. In one embodiment of the organic EL element of this embodiment, Z2 is a sulfur atom.
[0185] In one embodiment of the organic EL element of this embodiment, R Y1 ~R Y8 , R Y11 ~R Y14 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms.
[0186] In one embodiment of the organic EL element of this embodiment, R Y1 ~R Y8 , R Y11 ~R Y14 This is a hydrogen atom. In one embodiment of the organic EL element of this embodiment, R Y1 ~R Y8 , R Y11 ~R Y14 R is a hydrogen atom, Y1 ~R Y8 , R Y11 ~R Y14 At least one of them is a deuterium atom. This is preferable. In one embodiment of the organic EL element of this embodiment, R Y1 ~R Y8 , R Y11 ~R Y14 It is a deuterium atom.
[0187] In one embodiment of the organic EL element of this embodiment, the excitation resistance of the first host material is improved by having at least one group selected from the group consisting of groups represented by formulas (HY1), (HY10), (HY11), (HY12), and (HY13) in the molecule. By using such a first host material in the first light-emitting layer, the lifespan of the organic EL element is easily extended.
[0188] One embodiment of the organic EL element according to this embodiment, Ar 201 Or Ar 202 These are substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms.
[0189] One embodiment of the organic EL element according to this embodiment, Ar 201 Or Ar 202 This is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted benzoanthryl group, or a substituted or unsubstituted triphenylenyl group.
[0190] In one embodiment of the organic EL element of this embodiment, R in the first host material Y1 ~R Y8 , R Y11 ~R Y14 At least one of them is a deuterium atom.
[0191] One embodiment of the organic EL element according to this embodiment, Ar 201 and Ar 202 These are, independently, substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms. One embodiment of the organic EL element according to this embodiment, Ar 201 and Ar 202 These are, independently, substituted or unsubstituted ring-forming aryl groups with 6 to 18 carbon atoms.
[0192] One embodiment of the organic EL element according to this embodiment, Ar 201 and Ar 202 These are, independently, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted benzoanthryl group, or a substituted or unsubstituted triphenylenyl group.
[0193] According to this embodiment, one embodiment of the organic EL element, L 201 and L 202 These are, independently, single-bonded, substituted, or unsubstituted ring-forming arylene groups with 6 to 18 carbon atoms. According to this embodiment, one embodiment of the organic EL element, L 201 and L 202 Each of these is independently a single-bonded, substituted, or unsubstituted ring-forming arylene group with 6 to 13 carbon atoms.
[0194] In one embodiment of the organic EL element according to this embodiment, -L 201 -Ar 201 The group represented by -L 202 -Ar 202 At least one of the groups represented by is independently a group represented by one of the following formulas (2-11a) to (2-41a). In one embodiment of the organic EL element according to this embodiment, -L 201 -Ar 201 The group represented by -L 202 -Ar 202 Each of the groups represented by is independently a group represented by one of the following formulas (2-11a) to (2-41a). In one embodiment of the organic EL element according to this embodiment, -L 201 -Ar 201 The group represented by -L 202 -Ar 202 Each of the groups represented by is independently a group represented by one of the following formulas (2-11a) to (2-41a).
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[0198] (In formulas (2-11a) to (2-41a) above, Ra to Rg are each independently a hydrogen atom, an unsubstituted C1-C50 alkyl group, an unsubstituted C2-C50 alkenyl group, an unsubstituted C2-C50 alkynyl group, an unsubstituted ring-forming C3-C50 cycloalkyl group, 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 unsubstituted aralkyl group with 7 to 50 carbon atoms, -C(=O)R 801 The base represented by -COOR 802 A group is selected from the group consisting of a group represented by , a halogen atom, a cyano group, a nitro group, and an unsubstituted ring-forming aryl group having 6 to 50 carbon atoms. R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each of these is R in the host material. 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 This is synonymous, and * indicates the binding position.
[0199] In one embodiment of the organic EL element according to this embodiment, Ra to Rg are hydrogen atoms. In one embodiment of the organic EL element according to this embodiment, at least one of Ra to Rg is a deuterium atom. In one embodiment of the organic EL element according to this embodiment, Ra to Rg are hydrogen atoms, and at least one of Ra to Rg is a deuterium atom. In one embodiment of the organic EL element according to this embodiment, Ra to Rg are deuterium atoms.
[0200] In one embodiment of the organic EL element according to this embodiment, the first host material (compound represented by formula (2)) is a compound represented by formula (201), formula (202), formula (203), formula (204), formula (205), formula (206), formula (207), formula (208), or formula (209).
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[0210] (In the above equations (201) to (209), L 201 and Ar 201 L in equation (2) above is 201 and Ar 201 It is synonymous with, R 201 ~R 208 These are, respectively, R in equation (2) above. 201 ~R 208 (This is synonymous with...)
[0211] One embodiment of the organic EL element according to this embodiment, R 201 ~R 208 These are, independently, a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, and -Si(R 901 )(R 902 )(R 903 The group is represented by ), a cyano group, 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.
[0212] One embodiment of the organic EL element according to this embodiment, R 201 ~R 208 This is a hydrogen atom. One embodiment of the organic EL element according to this embodiment, R 201 ~R 208 At least one of them is a deuterium atom.
[0213] In one embodiment of the organic EL element of this embodiment, Ar in the first host material 201 Ar 202 , L 201 and L 202 At least one of the hydrogen atoms it possesses is a deuterium atom. In one embodiment of the organic EL element according to this embodiment, L in the first host material 201 and L 202 At least one of the hydrogen atoms it possesses is a deuterium atom. In one embodiment of the organic electroluminescent element according to this embodiment, Ar in the first host material 201 and Ar 202 At least one of the hydrogen atoms it possesses is a deuterium atom.
[0214] In the first host material, the substituents in the case of "substituted or unsubstituted" are preferably, independently, a halogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring-forming atoms.
[0215] In the first host material, the substituents in the case of "substituted or unsubstituted" are preferably, independently, an unsubstituted C1-C6 alkyl group, an unsubstituted ring-forming C6-C13 aryl group, or an unsubstituted ring-forming C5-C13 heterocyclic group.
[0216] In the first host material, the substituents in the case of "substituted or unsubstituted" are preferably, independently, an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 10 ring-forming atoms.
[0217] In one embodiment of the organic EL element of this embodiment, the groups described as "substituted or unsubstituted" in the first host material are all "unsubstituted" groups.
[0218] In the following explanation, a "first host material having at least one deuterium atom (a compound represented by formula (2))" is sometimes referred to as a "deuterated compound," and a compound in which all of the hydrogen atoms in the first host material are light hydrogen atoms is sometimes referred to as a "non-deuterated compound."
[0219] In an organic EL element according to one embodiment, the content of the non-deuterated compound in the first light-emitting layer, relative to the total of the deuterated compound (first host material having at least one deuterium atom) and the non-deuterated compound, is 99 mol% or less. The content of the non-deuterated compound can be confirmed by mass spectrometry. Furthermore, in an organic EL element according to one embodiment, the light-emitting layer contains a deuterated compound (a first host material having at least one deuterium atom) and a non-deuterated compound, and the proportion of the deuterated compound in relation to the total is 30 mol% or more, 50 mol% or more, 70 mol% or more, 90 mol% or more, 95 mol% or more, 99 mol% or more, or 100 mol%.
[0220] In an organic EL element according to one embodiment, It is preferable that 10% or more of the hydrogen atoms in the first host material (deuterated compound) are deuterium atoms. It is also preferable that 20% or more of the hydrogen atoms in the first host material (deuterated compound) are deuterium atoms. It is also preferable that 30% or more of the hydrogen atoms in the first host material (deuterated compound) are deuterium atoms. It is also preferable that 40% or more of the hydrogen atoms in the first host material (deuterated compound) are deuterium atoms. It is also preferable that 50% or more of the hydrogen atoms in the first host material (deuterated compound) are deuterium atoms. It is also preferable that 60% or more of the hydrogen atoms in the first host material (deuterated compound) are deuterium atoms. It is also preferable that 70% or more of the hydrogen atoms in the first host material (deuterated compound) are deuterium atoms. It is also preferable that 80% or more of the hydrogen atoms in the first host material (deuterated compound) are deuterium atoms. Note that the percentage indicating the proportion of deuterium atoms in the first host material is a percentage calculated based on the number of hydrogen atoms.
[0221] The presence of deuterium atoms in the first host material can be determined by mass spectrometry or 1This will be confirmed by 1H-NMR analysis. Furthermore, the bonding position of the deuterium atom in the first host material is: 1 It is identified by 1H-NMR analysis. Specifically, it is as follows: Mass spectrometry of the target compound revealed that its molecular weight is 1 higher than that of a corresponding compound where all hydrogen atoms are light hydrogen atoms, confirming the presence of one deuterium atom. Furthermore, the deuterium atom... 1 Since no signal was detected by H-NMR analysis, the target compound... 1 The number of deuterium atoms contained in the molecule can be determined by the integral value obtained by 1H-NMR analysis. 1 By performing 1H-NMR analysis and assigning the signal, the bonding position of the deuterium atom can be identified. In the following explanation, a "first host material having at least one deuterium atom" is sometimes referred to as a "deuterated compound," while a first host material in which all of its hydrogen atoms are light hydrogen atoms may be referred to as a "non-deuterated compound."
[0222] (Method for manufacturing the first host material) The first host material can be manufactured by known methods. The first host material can be manufactured, for example, by the following method. First, non-deuterated compounds are prepared by well-known coupling and substitution reactions. Then, using a precursor material of the deuterated compound, or more generally, in the presence of a Lewis acid H / D exchange catalyst (such as aluminum trichloride or ethyl aluminum chloride), the non-deuterated compound is treated with a deuterating solvent (such as d6-benzene). Both "deuterated compounds" and "non-deuterated compounds" can be produced by following known methods and using known alternative reactions and raw materials suited to the target product.
[0223] (Specific example of the first host material) Examples of the first host material include the following compounds. However, the present invention is not limited to these examples of the first host material. In the following examples, "D" represents a deuterium atom. Examples of the first host material also include non-deuterated compounds. Of the hydrogen atoms in the non-deuterated compound, at least one is a deuterium atom.
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[0279] In the following specific examples of compounds, D represents a deuterium atom, z, z1, z2, z3, z4, z5, and z6 each represent the number of deuterium atoms bonded to the ring, z is an integer between 1 and 8, z1 is an integer between 1 and 9, z2 to z5 are integers between 1 and 5, and z6 is an integer between 1 and 7.
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[0289] In the following specific examples of compounds, D represents a deuterium atom, z, z1, z2, z3, z4, z5, and z6 each represent the number of deuterium atoms bonded to the ring, z is an integer between 1 and 8, z1 is an integer between 1 and 9, z2 to z5 are integers between 1 and 5, and z6 is an integer between 1 and 7.
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[0298] <First luminescent compound> In one embodiment of the organic EL element according to this embodiment, the luminescent compound contained in the first light-emitting layer is the first luminescent compound. In one embodiment of the organic EL element according to this embodiment, the first light-emitting layer contains a first light-emitting compound that exhibits light emission with a maximum peak wavelength of 430 nm or more and 480 nm or less. In one embodiment of the organic EL element according to this embodiment, the first luminescent compound is at least one dopant material selected from the group consisting of fluorescent luminescent materials and phosphorescent luminescent materials shown below. Specific examples of fluorescent luminescent materials and phosphorescent luminescent materials include, for example, the following materials, but the present invention is not limited to these materials.
[0299] Examples of blue fluorescent materials that can be used in the light-emitting layer include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluorantene derivatives, fluorene derivatives, diamine derivatives, and triarylamine derivatives. Specifically, these include N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviated as YGA2S), 4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviated as YGAPA), and 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCBAPA).
[0300] Aromatic amine derivatives can be used as green fluorescent luminescent materials that can be used in the light-emitting layer. Specifically, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[ Examples include 9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), and N,N,9-triphenylanthracene-9-amine (abbreviation: DPhAPhA).
[0301] As red fluorescent materials that can be used in the light-emitting layer, tetracene derivatives and diamine derivatives can be used. Specifically, examples include N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviated as p-mPhTD) and 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluorantene-3,10-diamine (abbreviated as p-mPhAFD).
[0302] Metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used as blue phosphorescent materials that can be used in the light-emitting layer. Specifically, examples include bis[2-(4',6'-difluorophenyl)pyridinate-N,C2']iridium(III)tetrakis(1-pyrazolyl)borate (abbreviated as FIr6), bis[2-(4',6'-difluorophenyl)pyridinate-N,C2']iridium(III) picolinate (abbreviated as FIrpic), bis[2-(3',5'bistrifluoromethylphenyl)pyridinate-N,C2']iridium(III) picolinate (abbreviated as Ir(CF3ppy)2(pic)), and bis[2-(4',6'-difluorophenyl)pyridinate-N,C2']iridium(III) acetylacetonate (abbreviated as FIracac).
[0303] Iridium complexes and the like are used as green phosphorescent materials that can be used in the light-emitting layer. Examples include tris(2-phenylpyridinato-N,C2')iridium(III) (abbreviation: Ir(ppy)3), bis(2-phenylpyridinato-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazolato)iridium(III) acetylacetonate (abbreviation: Ir(pbi)2(acac)), and bis(benzo[h]quinolinate)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)).
[0304] Metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used as red phosphorescent materials that can be used in the light-emitting layer. Specifically, examples include organometallic complexes such as bis[2-(2'-benzo[4,5-α]thienyl)pyridinate-N,C3']iridium(III) acetylacetonate (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinolinate-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP). Furthermore, rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: Eu(DBM)3(Phen)), and tris[1-(2-tenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: Eu(TTA)3(Phen)) can be used as phosphorescent compounds because the emission is due to electron transitions between different multiplicities from rare earth metal ions.
[0305] In one embodiment of the organic EL element according to this embodiment, the first light-emitting compound is at least one compound selected from the group consisting of the compound represented by formula (5), the compound represented by formula (6), and the compound represented by formula (3A).
[0306] (The compound represented by formula (5)) In one embodiment of the organic EL element according to this embodiment, the first light-emitting compound is a compound represented by the following formula (5).
[0307] [ka]
[0308] (In the above 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 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 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 )(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 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.
[0309] In the first luminescent compound, 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. Preferably, 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 901 If multiple R 901 They are either identical or different from one another. R 902If 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.
[0310] "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 R 506 and R 507 A group consisting of R 501 and R 502 and R 503 This is a combination of sets and other elements.
[0311] In one embodiment, the compound represented by formula (5) is the compound represented by the following formula (52).
[0312] [ka]
[0313] (In the above 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 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 531 ~R 534 , 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.
[0314] (The compound represented by formula (6)) In one embodiment of the organic EL element according to this embodiment, the first light-emitting compound is a compound represented by the following formula (6).
[0315] [ka]
[0316] (In the above 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 R602 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.
[0317] In one embodiment of the organic EL element according to this embodiment, the a-ring, b-ring, and c-ring are rings that condense into the central condensed bi-ring structure of formula (6) composed 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).
[0318] The aromatic hydrocarbon rings of rings a, b, and c have the same structure as compounds in which a hydrogen atom has been introduced to an aryl group. The "aromatic hydrocarbon ring" of ring a includes three carbon atoms on the central condensed biring structure of 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 formula (6) as ring-forming atoms.
[0319] 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 contains three carbon atoms on the central fused biring structure of formula (6) as ring-forming atoms. The heterocycles of rings b and c contain two carbon atoms on the central fused biring structure of 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.
[0320] 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 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 601 A 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. R 601 and R 602 Each of these elements does not necessarily have to be bonded to an a-ring, b-ring, or c-ring independently.
[0321] In one embodiment, the a-ring, b-ring, and c-ring in 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 formula (6) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.
[0322] In one embodiment, R in 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.
[0323] In one embodiment, the compound represented by formula (6) is the compound represented by the following formula (62).
[0324] [ka]
[0325] (In formula (62) above, 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. R 602A 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 connect with 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. (In the above formula (62), 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 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 to one another.
[0326] R in equation (62) above 601A and R 602A These are, respectively, R in equation (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 R613 When they are joined, and R 602A and R 614 The same applies when they are joined together.
[0327] 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 612 These 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.
[0328] In one embodiment, the compound represented by formula (6) is the compound represented by the following formula (42-2).
[0329] [ka]
[0330] (In the above formula (42-2), R 611 ~R 617 , R 601A and R 602A Each of these independently corresponds to R in equation (62) above. 611 ~R 617 , R 601A and R 602A It is synonymous with, X4 is an oxygen atom or a sulfur atom. R 701 ~R 704 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 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 701 ~R 704 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. In the above equation (42-2), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 Each of these independently corresponds to R in equation (62) above. 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 (This is synonymous with...)
[0331] (The compound represented by formula (3A)) In one embodiment of the organic EL element according to this embodiment, the first light-emitting compound is a compound represented by the following formula (3A).
[0332] [ka]
[0333] (In the above formula (3A), Ra 301 Ra 302 Ra 303 Ra 304 Ra 305 Ra 306 Ra 307 Ra 308 Ra 309 and Ra 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 connect with each other, Ra 301 ~Ra 310 At least one of them is a monovalent group represented by the following formula (31A), Ra that does not form the monocyclic ring, does not form the fused ring, and is not a monovalent group represented by the following formula (31A) 301 ~Ra 310 Each of these independently consists of a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, 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 907The group is represented by ), a halogen atom, a cyano group, a nitro group, 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.
[0334] [ka]
[0335] (In the above formula (31A), Ara 301 and Ara 302 Each is independently 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, and La 301 , La 302 and La 303 Each of these is independently an arylene group with 6 to 30 ring-forming carbon atoms, either single-bonded, substituted, or unsubstituted, or a divalent heterocyclic group with 5 to 30 ring-forming atoms, and * indicates the bond position in the pyrene ring in formula (3A).
[0336] (Specific examples of first luminescent compounds) The following are specific examples of the first type of luminescent compound, but these are merely examples, and luminescent compounds are not limited to the examples listed below.
[0337] [ka]
[0338] In one embodiment of the organic EL element of this embodiment, the first luminescent compound exhibits luminescence with a maximum peak wavelength of 500 nm or less. In one embodiment of the organic EL element of this embodiment, the first luminescent compound exhibits emission with a maximum peak wavelength of 480 nm or less, or emission with a maximum peak wavelength of 470 nm or less. In one embodiment of the organic EL element of this embodiment, the first luminescent compound exhibits emission with a maximum peak wavelength of 430 nm or higher, or emission with a maximum peak wavelength of 440 nm or higher.
[0339] In one embodiment of the organic EL element of this embodiment, the first luminescent compound exhibits fluorescence emission with a maximum peak wavelength of 500 nm or less, fluorescence emission with a maximum peak wavelength of 480 nm or less, or fluorescence emission with a maximum peak wavelength of 470 nm or less. In one embodiment of the organic EL element of this embodiment, the first luminescent compound exhibits fluorescence emission with a maximum peak wavelength of 430 nm or higher, or fluorescence emission with a maximum peak wavelength of 440 nm or higher.
[0340] (Method for measuring the maximum peak wavelength) A luminescent compound (the compound to be measured for maximum peak wavelength) and a host material are co-deposited onto a quartz substrate (25 × 25 mm) so that the mass-based ratio of the luminescent compound to the host material in the luminescent layer (luminescent compound / host material) is the same, thereby forming a 50 nm thick film for measurement. Next, the quartz substrate on which the film for measurement is formed and a sealing glass coated with a desiccant are bonded together using an ultraviolet-curing resin to seal the film for measurement. The outer dimensions of the sealing glass are 17 × 17 mm, the inner dimensions are 13 × 13 mm, and the recess depth is 0.5 mm. As the desiccant, for example, OleDry-P2 manufactured by Futaba Corporation can be used. As the ultraviolet-curing resin, for example, TB3124N(IE) manufactured by ThreeBond Fine Chemicals, Inc. can be used. A fluorescence spectrum analyzer is used for PL spectrum measurement. The measurement conditions are as follows: The maximum peak wavelength λ (unit: nm) of the film is calculated from the PL spectrum obtained by exciting the film sample at a specific wavelength (a value obtained by shortening the maximum peak wavelength of the absorption spectrum by 30 nm). The maximum peak wavelength obtained in this way is sometimes called the maximum peak wavelength of fluorescence emission (FL-peak). As a fluorescence spectrum analyzer, for example, a spectrofluorometer F-7000 (manufactured by Hitachi High-Tech Science Corporation) can be used. The maximum peak wavelength of the absorption spectrum used to determine the wavelength of light that excites the film sample can be measured using the singlet energy S1 measurement method using a solution (solution method), which will be described later. In this solution method, a toluene solution of the compound to be measured (luminescent compound) is prepared.
[0341] In one embodiment of the organic EL element according to this embodiment, the full width at half maximum of the largest peak of the first luminescent compound is 1 nm or more and 20 nm or less. In one embodiment of the organic EL element of this embodiment, the first light-emitting compound is a compound that does not contain an azine ring structure in its molecule.
[0342] In one embodiment of the organic EL element of this embodiment, the first luminescent compound is not a boron-containing complex.
[0343] In one embodiment of the organic EL element of this embodiment, the first light-emitting layer does not contain a metal complex. Also, in one embodiment of the organic EL element of this embodiment, the first light-emitting layer does not contain a boron-containing complex.
[0344] In one embodiment of the organic EL element of this embodiment, the first light-emitting layer does not contain a phosphorescent material. Also, in one embodiment of the organic EL element of this embodiment, the first light-emitting layer does not contain a heavy metal complex or a phosphorescent rare earth metal complex. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.
[0345] In one embodiment of the organic EL element according to this embodiment, the triplet energy T1(H1) of the first host material and the triplet energy T1(D1) of the first luminescent compound satisfy the following equation (Equation 6). T1(D1)>T1(H1) …(Math 6)
[0346] For example, when the emission band includes two emission layers (a first emission layer and a second emission layer), if the first luminescent compound and the first host material satisfy the relationship in equation (equation 6), then when triplet excitons generated in the second emission layer move to the first emission layer, they transfer energy to the molecules of the first host material rather than to the first luminescent compound which has a higher triplet energy. Furthermore, triplet excitons generated by the recombination of holes and electrons on the first host material do not move to the first luminescent compound which has a higher triplet energy. Triplet excitons generated by recombination on the molecules of the first luminescent compound rapidly transfer energy to the molecules of the first host material. Triplet excitons from the first host material do not move to the first luminescent compound; instead, singlet excitons are generated through efficient collisions between triplet excitons on the first host material via the TTF phenomenon.
[0347] In one embodiment of the organic EL device according to this embodiment, the singlet energy S1(H1) of the first host material and the singlet energy S1(D1) of the first luminescent compound satisfy the following equation (Equation 5). The singlet energy S1 refers to the energy difference between the lowest excited singlet state and the ground state. S1(H1)>S1(D1) …(Math 5)
[0348] When the first host material and the first luminescent compound satisfy the relationship shown in equation (Equation 5), singlet excitons generated on the first host material can easily transfer energy from the first host material to the first luminescent compound, contributing to the fluorescence emission of the first luminescent compound.
[0349] (Triplet energy T1) The following methods can be used to measure the triplet energy T1. The compound to be measured is placed in EPA (diethyl ether:isopentane:ethanol = 5:5:2 (volume ratio)) and 10 -5 mol / L or more 10 -4 Dissolve the substance to a concentration of mol / L or less to obtain a solution, and place this solution in a quartz cell to use as the measurement sample. Measure the phosphorescence spectrum of this sample at a low temperature (77[K]) (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength). Draw a tangent line to the rising edge of the short-wavelength side of this phosphorescence spectrum, and measure the wavelength λ at the intersection of this tangent line and the horizontal axis. edge Based on [nm], the amount of energy calculated from the following conversion formula (F1) is defined as the triplet energy T1. Conversion formula (F1): T1[eV]=1239.85 / λ edge
[0350] The tangent to the rise of the phosphorescence spectrum on the short-wavelength side is drawn as follows: When moving along the spectral curve from the short-wavelength side of the phosphorescence spectrum to the shortest wavelength maximum value of the spectrum, consider the tangent at each point on the curve toward the long-wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope value is maximum (i.e., the tangent at the inflection point) is considered the tangent to the rise of the phosphorescence spectrum on the short-wavelength side. Furthermore, maxima with peak intensity less than 15% of the maximum peak intensity of the spectrum are not included in the shortest wavelength maxima mentioned above. Instead, the tangent line drawn at the point closest to the shortest wavelength maxima, where the slope value is at its maximum, is considered the tangent line to the rising edge of the phosphorescence spectrum on the short wavelength side. For phosphorescence measurement, a Hitachi High-Technologies Corporation F-4500 spectrofluorometer can be used. However, the measuring apparatus is not limited to this; measurements may also be performed by combining a cooling device, a low-temperature container, an excitation light source, and a light-receiving device.
[0351] (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).
[0352] 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.
[0353] In one embodiment of the organic EL element according to this embodiment, the first light-emitting layer contains a first light-emitting compound in an amount of 0.5% by mass or more of the total mass of the first light-emitting layer. In one embodiment of the organic EL element according to this embodiment, the first light-emitting layer contains a first light-emitting compound in an amount of 10% by mass or less, 7% by mass or less, or 5% by mass or less of the total mass of the first light-emitting layer.
[0354] In one embodiment of the organic EL element according to this embodiment, the first light-emitting layer contains the first host material in an amount of 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more of the total mass of the first light-emitting layer. In one embodiment of the organic EL element according to this embodiment, the first light-emitting layer contains the first host material in an amount of 99.5% by mass or less, or 99% by mass or less, of the total mass of the first light-emitting layer. However, if the first light-emitting layer contains a first host material and a first light-emitting compound, the upper limit of the total content of the first host material and the first light-emitting compound is 100% by mass.
[0355] This embodiment does not exclude the first light-emitting layer from containing materials other than the first host material and the first light-emitting compound. The first light-emitting layer may contain only one type of first host material, or two or more types. The first light-emitting layer may contain only one type of first light-emitting compound, or two or more types.
[0356] In one embodiment of the organic EL element according to this embodiment, the first light-emitting layer may consist only of a first host material and a first light-emitting compound.
[0357] (Thickness of the first light-emitting layer) In one embodiment of the organic EL element according to this embodiment, the thickness of the first light-emitting layer is preferably 5 nm or more and 50 nm or less, more preferably 5 nm or more and 30 nm or less, and even more preferably 5 nm or more and 15 nm or less. When the thickness of the first light-emitting layer is 5 nm or more, it is easier to form the light-emitting layer and easier to adjust the chromaticity. When the thickness of the first light-emitting layer is 50 nm or less, it is easier to suppress the rise in the driving voltage.
[0358] In one embodiment of the organic EL element according to this embodiment, when the light emission band includes a first light emission layer and a second light emission layer, the thickness of the first light emission layer is preferably 5 nm or more, and more preferably 15 nm or more. If the thickness of the first light emission layer is 5 nm or more, when the light emission region has a second light emission layer, it is easier to suppress triplet excitons that have moved from the second light emission layer to the first light emission layer from returning to the second light emission layer. Furthermore, if the thickness of the first light emission layer is 5 nm or more, triplet excitons can be completely separated from the recombination portion in the second light emission layer. Furthermore, if the emission band includes the first and second emission layers, the thickness of the first emission layer is preferably 20 nm or less. If the thickness of the first emission layer is 20 nm or less, the density of triplet excitons in the first emission layer can be increased, making the TTF phenomenon even more likely to occur. In one embodiment of the organic EL element according to this embodiment, the thickness of the first light-emitting layer is preferably 5 nm or more and 20 nm or less.
[0359] (Second light-emitting layer) In one embodiment of the organic EL element according to this embodiment, the light-emitting band includes a first light-emitting layer and a second light-emitting layer. In one embodiment of the organic EL element according to this embodiment, the second light-emitting layer may be included between the first light-emitting layer and the cathode, or between the first light-emitting layer and the anode.
[0360] In one embodiment of the organic EL element according to this embodiment, the second light-emitting layer includes a second host material and a second light-emitting compound. The second light-emitting compound is preferably a dopant material. The first light-emitting compound and the second light-emitting compound are either identical or different from each other. In one embodiment of the organic EL element according to this embodiment, the first host material and the second host material are different from each other. The second light-emitting layer contains, for example, a second host material in an amount of 50% by mass or more of the total mass of the second light-emitting layer. In one embodiment of the organic EL element according to this embodiment, the second luminescent compound can be at least one dopant material selected from the group consisting of the aforementioned fluorescent luminescent materials and phosphorescent luminescent materials, similar to the first luminescent compound. In one embodiment of the organic EL element according to this embodiment, the second light-emitting compound is at least one compound selected from the group consisting of the compound represented by formula (5), the compound represented by formula (6), and the compound represented by formula (3A). The compounds used as the second host material will be described later.
[0361] In one embodiment of the organic EL element according to this embodiment, the second luminescent compound exhibits luminescence with a maximum peak wavelength of 500 nm or less. In one embodiment of the organic EL element according to this embodiment, the second luminescent compound exhibits emission with a maximum peak wavelength of 480 nm or less, or emission with a maximum peak wavelength of 470 nm or less. In one embodiment of the organic EL element according to this embodiment, the second luminescent compound exhibits emission with a maximum peak wavelength of 430 nm or more, or emission with a maximum peak wavelength of 440 nm or more. In one embodiment of the organic EL element according to this embodiment, the second luminescent compound is a blue luminescent compound.
[0362] In one embodiment of the organic EL element according to this embodiment, the second luminescent compound exhibits fluorescence emission with a maximum peak wavelength of 500 nm or less, fluorescence emission with a maximum peak wavelength of 480 nm or less, or fluorescence emission with a maximum peak wavelength of 470 nm or less. In one embodiment of the organic EL element according to this embodiment, the second luminescent compound exhibits fluorescence emission with a maximum peak wavelength of 430 nm or higher, or fluorescence emission with a maximum peak wavelength of 440 nm or higher. The method for measuring the maximum peak wavelength of a compound is as described above.
[0363] In one embodiment of the organic EL element according to this embodiment, the full width at half maximum of the largest peak of the second light-emitting compound is 1 nm or more and 20 nm or less.
[0364] In one embodiment of the organic EL element according to this embodiment, the second light-emitting compound is a compound that does not contain an azine ring structure in its molecule.
[0365] In one embodiment of the organic EL element according to this embodiment, the second luminescent compound is not a boron-containing complex.
[0366] In one embodiment of the organic EL element according to this embodiment, the second light-emitting layer does not contain a metal complex. Also, in one embodiment of the organic EL element according to this embodiment, the second light-emitting layer does not contain a boron-containing complex.
[0367] In one embodiment of the organic EL element according to this embodiment, the second light-emitting layer does not contain a phosphorescent material. Furthermore, in one embodiment of the organic EL element according to this embodiment, the second light-emitting layer does not contain heavy metal complexes or phosphorescent rare-earth metal complexes.
[0368] In one embodiment of the organic EL element according to this embodiment, when the first light-emitting layer includes a first host material and the second light-emitting layer includes a second host material, it is preferable that the triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material satisfy the following equation (Equation 1A). T1(H2) > T1(H1) …(Math 1A)
[0369] In the organic EL element according to this embodiment, by having an emission band that includes a first emission layer and a second emission layer satisfying the relationship in the above formula (Equation 1A), the luminous efficiency is improved compared to an emission band composed of a single emission layer.
[0370] Conventionally, Triplet-Triplet-Annihilation (sometimes referred to as TTA) has been known as a technique for improving the luminescence efficiency of organic electroluminescent devices. TTA is a mechanism in which triplet excitons collide with other triplet excitons to produce singlet excitons. The TTA mechanism is sometimes referred to as the TTF mechanism. TTF is an abbreviation for Triplet-Triplet Fusion.
[0371] This explains the TTF phenomenon. Holes injected from the anode and electrons injected from the cathode recombine in the light-emitting layer to generate excitons. As previously known, their spin states are 25% singlet excitons and 75% triplet excitons. In conventionally known fluorescent devices, 25% of singlet excitons emit light when they relax to the ground state, while the remaining 75% of triplet excitons return to the ground state through a thermal deactivation process without emitting light. Therefore, the theoretical limit of the internal quantum efficiency of conventional fluorescent devices was said to be 25%. Meanwhile, the behavior of triplet excitons generated within organic matter has been theoretically investigated. According to SMBachilo et al. (J.Phys.Chem.A,104,7711(2000)), assuming that higher-order excitons such as quintets quickly revert to triplets, triplet excitons (hereinafter, 3 A * When the density of (described as) increases, triplet excitons collide with each other, and the reaction shown in the following equation occurs. Here, 1 A represents the ground state, 1 A * This represents the lowest excited singlet exciton. 3 A * + 3 A * →(4 / 9) 1 A+(1 / 9) 1 A * +(13 / 9) 3 A * That is, 5 3 A * →4 1 A+1A *Therefore, it is predicted that 1 / 5, or 20%, of the 75% of triplet excitons initially generated will be converted into singlet excitons. Consequently, the singlet excitons contributing as light will be 40%, which is the initial 25% plus 75% × (1 / 5) = 15%. In this case, the ratio of emission from TTF to the total emission intensity (TTF ratio) will be 15 / 40, or 37.5%. Furthermore, if we assume that the 75% of the initially generated triplet excitons collide with each other to generate singlet excitons (one singlet exciton is generated from two triplet excitons), then a very high internal quantum efficiency of 62.5% is obtained, which is the initial 25% of singlet excitons plus 75% × (1 / 2) = 37.5%. In this case, the TTF ratio is 37.5 / 62.5 = 60%.
[0372] In one embodiment of the organic EL element according to this embodiment, by satisfying the relationship in the above formula (Equation 1A), it is considered that triplet excitons generated by the recombination of holes and electrons in the second light-emitting layer are less likely to be quenched at the interface between the second light-emitting layer and the organic layer in direct contact with the second light-emitting layer, even if there is an excess of carriers at the interface between the second light-emitting layer and the organic layer in direct contact with the second light-emitting layer. For example, if the recombination region is locally located at the interface between the second light-emitting layer and the hole transport layer or electron barrier layer, quenching by an excess of electrons is possible. On the other hand, if the recombination region is locally located at the interface between the second light-emitting layer and the electron transport layer or hole barrier layer, quenching by an excess of holes is possible. One embodiment of the organic EL element according to this embodiment includes a first light-emitting layer and a second light-emitting layer that satisfy the relationship in the above formula (Equation 1A). As a result, triplet excitons generated in the second light-emitting layer move to the first light-emitting layer without being quenched by excess carriers, and reverse movement from the first light-emitting layer to the second light-emitting layer is suppressed. Consequently, the TTF mechanism is activated in the first light-emitting layer, singlet excitons are efficiently generated, and the luminescence efficiency is improved. Thus, the organic EL device comprises a second light-emitting layer that primarily generates triplet excitons and a first light-emitting layer that primarily exhibits the TTF mechanism by utilizing triplet excitons migrated from the second light-emitting layer, as separate regions. By using a compound with a lower triplet energy than the second host material in the second light-emitting layer as the first host material in the first light-emitting layer, a difference in triplet energy is created, thereby improving the luminescence efficiency. In the case of the tandem type organic EL element described later, at least one of the multiple light-emitting units has a first light-emitting layer and a second light-emitting layer, and the triplet energy T1(H1) of the first host material in the first light-emitting layer and the triplet energy T1(H2) of the second host material in the second light-emitting layer satisfy the relationship in the above formula (Equation 1A), thereby achieving an improvement in luminous efficiency due to the TTA mechanism.
[0373] In the organic EL element according to this embodiment, it is preferable that the triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material satisfy the following equation (Equation 1B). T1(H2) - T1(H1) > 0.03eV …(Math 1B)
[0374] In one embodiment of the organic EL element according to this embodiment, the first light-emitting layer and the second light-emitting layer are in direct contact.
[0375] In this specification, the layer structure in which "the first light-emitting layer and the second light-emitting layer are in direct contact" may also include, for example, any of the following embodiments (LS1), (LS2), and (LS3). (LS1) A configuration in which, during the process of depositing the compound relating to the first light-emitting layer and the process of depositing the compound relating to the second light-emitting layer, a region is created in which both the first host material and the second host material are mixed, and this region is located at the interface between the first light-emitting layer and the second light-emitting layer. (LS2) In a configuration in which the first light-emitting layer and the second light-emitting layer contain a luminescent compound, a region in which the first host material, the second host material, and the luminescent compound are mixed is generated during the process of vapor deposition of the compound relating to the first light-emitting layer and the vapor deposition of the compound relating to the second light-emitting layer, and this region is located at the interface between the first light-emitting layer and the second light-emitting layer. (LS3) A configuration in which, when the first light-emitting layer and the second light-emitting layer contain a light-emitting compound, a region made of the light-emitting compound, a region made of the first host material, or a region made of the second host material is generated during the process of vapor deposition of the compound relating to the first light-emitting layer and the vapor deposition of the compound relating to the second light-emitting layer, and such region is located at the interface between the first light-emitting layer and the second light-emitting layer.
[0376] In one embodiment of the organic EL element according to this embodiment, the first light-emitting layer is disposed between the anode and the second light-emitting layer.
[0377] In one embodiment of the organic EL element according to this embodiment, one of the first light-emitting layer and the second light-emitting layer is the layer located furthest to the anode among a plurality of layers having a light-emitting band.
[0378] In one embodiment of the organic EL element according to this embodiment, one of the first light-emitting layer and the second light-emitting layer is the layer located furthest to the cathode among a plurality of layers having a light-emitting band.
[0379] In the organic EL element according to this embodiment, the anode, the first light-emitting layer, the second light-emitting layer, and the cathode may be arranged in this order, or the order of the first light-emitting layer and the second light-emitting layer may be reversed. That is, the anode, the second light-emitting layer, the first light-emitting layer, and the cathode may be arranged in this order. Regardless of the order of the first light-emitting layer and the second light-emitting layer, by selecting a combination of materials that satisfies the relationship in the above formula (Equation 1A), the effects of a laminated configuration of the first light-emitting layer and the second light-emitting layer can be expected.
[0380] In one embodiment of the organic EL element according to this embodiment, the singlet energy S1(H2) of the second host material and the singlet energy S1(D2) of the second luminescent compound satisfy the following equation (Equation 7). S1(H2)>S1(D2)…(Number 7)
[0381] In the organic EL element according to this embodiment, the second luminescent compound and the second host material satisfy the relationship shown in equation (Equation 7). As a result, the singlet energy of the second luminescent compound is smaller than the singlet energy of the second host material. Therefore, singlet excitons generated by the TTF phenomenon transfer energy from the second host material to the second luminescent compound, contributing to the fluorescence emission of the second luminescent compound.
[0382] In one embodiment of the organic EL element according to this embodiment, the triplet energy T1(D2) of the second luminescent compound and the triplet energy T1(H2) of the second host material satisfy the following equation (Equation 8). T1(D2)>T1(H2) …(Math 8)
[0383] In the organic EL element according to this embodiment, the relationship between the second host material and the second luminescent compound satisfies the relationship shown in equation (Equation 8). As a result, triplet excitons generated in the second light-emitting layer move over the second host material rather than the second luminescent compound, which has a higher triplet energy, making it easier for them to move to the first light-emitting layer.
[0384] In one embodiment of the organic EL element according to this embodiment, the second light-emitting layer contains a second light-emitting compound in an amount of 0.5% by mass or more of the total mass of the second light-emitting layer. In one embodiment of the organic EL element according to this embodiment, the second light-emitting layer contains a second light-emitting compound in an amount of 10% by mass or less, 7% by mass or less, or 5% by mass or less of the total mass of the second light-emitting layer.
[0385] In one embodiment of the organic EL element according to this embodiment, the second light-emitting layer contains the second host material in an amount of 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more of the total mass of the second light-emitting layer. In one embodiment of the organic EL element according to this embodiment, the second light-emitting layer contains the second host material in an amount of 99.5% by mass or less, or 99% by mass or less, of the total mass of the second light-emitting layer. If the second light-emitting layer contains a second host material and a second light-emitting compound, the upper limit of the total content of the second host material and the second light-emitting compound is 100% by mass.
[0386] This embodiment does not exclude the possibility that the second light-emitting layer may contain materials other than the second host material and the second light-emitting compound. In one embodiment of the organic EL element according to this embodiment, the second light-emitting layer may contain only one type of second host material or two or more types. In one embodiment of the organic EL element according to this embodiment, the second light-emitting layer may contain only one type of second light-emitting compound or two or more types.
[0387] In one embodiment of the organic EL element according to this embodiment, the second light-emitting layer may consist only of a second host material and a second light-emitting compound.
[0388] In one embodiment of the organic EL element according to this embodiment, the thickness of the second light-emitting layer is preferably 3 nm or more, and more preferably 5 nm or more. If the thickness of the second light-emitting layer is 3 nm or more, it is a sufficient thickness for hole-electron recombination to occur in the second light-emitting layer. In one embodiment of the organic EL element according to this embodiment, the film thickness of the second light-emitting layer is preferably 15 nm or less, and more preferably 10 nm or less. If the film thickness of the second light-emitting layer is 15 nm or less, it is thin enough for triplet excitons to move to the first light-emitting layer. In one embodiment of the organic EL element according to this embodiment, the thickness of the second light-emitting layer is more preferably 3 nm or more and 15 nm or less.
[0389] <Tandem-type organic EL element> The organic EL element according to the first embodiment also preferably includes two or more light-emitting units arranged between the anode and the cathode, and a charge-generating unit (also referred to as an intermediate unit) arranged between at least one pair of light-emitting units selected from the two or more light-emitting units. In the organic EL element according to the first embodiment, it is preferable that one or more light-emitting bands are two or more light-emitting bands, and that the two or more light-emitting bands include at least a first light-emitting band and a second light-emitting band, and that one or more charge generation transport bands include a second charge generation transport band which includes a first organic layer (first acceptor material-containing layer). In this case, it is preferable that the second charge generation transport band is arranged between the first light-emitting band and the second light-emitting band, and that the first light-emitting band, the first organic layer, and the second light-emitting band are arranged in this order from the anode side. The second charge generation transport band is a charge generation unit as a charge generation band. An organic EL element in which a plurality of light-emitting units are stacked may be referred to as a tandem type organic EL element. One embodiment of the organic EL element according to the first embodiment is a tandem type organic EL element. In a tandem-type organic EL element, it is also preferable that one or more charge generation transport bands include a first charge generation transport band containing a first organic layer (first acceptor material-containing layer). In this case, it is preferable that the first charge generation transport band is located between the light emission band closest to the anode and the anode among the one or more light emission bands. In the tandem organic EL element according to this embodiment, by incorporating a compound represented by formula (AC1) in the first organic layer (for example, the charge generation band) and a deuterated, highly durable first host material (a compound represented by formula (2)) in the first light-emitting layer, appropriate light emission lifetime characteristics can be obtained even in elements where a large load is applied to the interface between the electron barrier layer and the first light-emitting layer. Therefore, tandem-type organic EL elements can suppress the generation of leakage current and achieve a longer lifespan.
[0390] Multiple light-emitting units arranged between the anode and cathode can be numbered sequentially from the anode side as the Xth stage, (X+1)th stage, (X+2)th stage, and so on (where X is an integer of 1 or more). For example, if the organic EL element according to the first embodiment includes two or more light-emitting units, the organic EL element includes at least the first stage light-emitting unit and the second stage light-emitting unit. The organic EL element according to the first embodiment may be a tandem type organic EL element including two or more stages of light-emitting units, or an organic EL element including only one stage of light-emitting units.
[0391] In a tandem organic EL element, it is preferable that two or more light-emitting units each contain one light-emitting band. Each light-emitting band may independently contain only one light-emitting layer or two or more light-emitting layers. However, at least one of the two or more light-emitting units contains a light-emitting band having a first light-emitting layer, and the first light-emitting layer contains a compound represented by formula (2) as the first host material. Each light-emitting layer preferably contains a host material and a light-emitting compound. In a tandem-type organic EL element, the luminescent compound is, for example, one or more compounds selected from the group consisting of a first luminescent compound and a second luminescent compound. In a tandem-type organic EL element, it is also preferable that at least one of the two or more light-emitting units includes a light-emitting band having a first light-emitting layer and a second light-emitting layer.
[0392] <Charge generation band> In a tandem-type organic EL element, it is preferable that at least one of the one or more charge generation and transport bands includes a charge generation unit as a charge generation band. The charge generation unit may also preferably include a first acceptor material-containing layer (first organic layer). In a tandem-type organic EL element, the charge transport band may include a first acceptor material-containing layer, and the charge generation unit may also include a first acceptor material-containing layer. In a tandem-type organic EL element, the charge transport band may not include the first acceptor material-containing layer, while the charge generation unit may include the first acceptor material-containing layer. In a tandem-type organic EL element, the charge transport band may include a first acceptor material-containing layer, and the charge generation unit may not include the first acceptor material-containing layer. In a tandem-type organic EL element, it is preferable that the first charge generation transport band, the first light emission band, the second charge generation transport band, and the second light emission band are arranged in this order from the anode side. In this case, it is also preferable that the first charge generation transport band includes the first organic layer and the second charge generation transport band includes the first organic layer. It is also preferable that the first charge generation transport band includes the first organic layer and the second charge generation transport band does not include the first organic layer. It is also preferable that the first charge generation transport band does not include the first organic layer and the second charge generation transport band includes the first organic layer.
[0393] In one embodiment of a tandem organic EL element, the charge generation unit, which serves as a charge generation band, includes one or more organic layers. Preferably, the charge generation unit includes one or more charge generation layers. Preferably, the charge generation layers are organic layers. More preferably, the charge generation unit includes two or more charge generation layers.
[0394] The charge generation layer is a layer that generates holes and electrons when a voltage is applied to the organic EL element. It supplies electrons to the layer located on the anode side of the charge generation layer and holes to the layer located on the cathode side of the charge generation layer. The charge generation layer may also be called an intermediate layer, intermediate electrode, intermediate conductive layer, electron extraction layer, connecting layer, or intermediate insulating layer.
[0395] In a tandem-type organic EL element, it is also preferable that at least one of the one or more charge generation layers is a first acceptor material-containing layer.
[0396] In a tandem-type organic EL element, the charge generation unit, which serves as a charge generation band, preferably includes two charge generation layers: a first charge generation layer and a second charge generation layer. The first charge generation layer and the second charge generation layer do not necessarily have to be in direct contact, but it is preferable that they are in direct contact. It is preferable that at least one of the first charge generation layer and the second charge generation layer is a first acceptor material-containing layer.
[0397] In a tandem-type organic EL element, it is preferable that the charge generation unit includes a first charge generation layer and a second charge generation layer in that order from the anode side. In this case, it is preferable that the second charge generation layer, which is located on the cathode side of the first charge generation layer, is a first acceptor material-containing layer.
[0398] In a tandem organic EL element, when a charge generation unit, which serves as a charge generation band, is composed of multiple charge generation layers, it is preferable that the charge generation unit includes an N-type charge generation layer that injects electrons into the light-emitting unit and a P-type charge generation layer that injects holes into the light-emitting unit. It is preferable that the N-type charge generation layer is in direct contact with the light-emitting unit located on the anode side of the charge generation unit. It is preferable that the P-type charge generation layer is in direct contact with the light-emitting unit located on the cathode side of the charge generation unit.
[0399] In a tandem organic EL element, it is preferable that one of the N-type charge generation layer and the P-type charge generation layer is a first charge generation layer. In a tandem organic EL element, it is also preferable that the N-type charge generation layer is the first charge generation layer and the P-type charge generation layer is the second charge generation layer.
[0400] In a tandem-type organic EL element, the P-type charge generation layer is preferably a first acceptor material-containing layer containing the compound represented by formula (AC1). Other materials that can be used in the charge generation layer of a charge generation unit include, for example, known materials that can be used in the charge generation layer of a tandem-type organic EL element.
[0401] In a tandem-type organic EL element, the second charge generation layer preferably contains a hole transport band material and an acceptor material. The second charge generation layer may also preferably contain a compound represented by formula (AC1) (first acceptor material) or a second acceptor material as the acceptor material. In a tandem-type organic EL element, the content of the acceptor material in the second charge generation layer is preferably less than 50% by mass, 40% by mass or less, 30% by mass or less, or 20% by mass or less. In a tandem-type organic EL element, it is also preferable that the content of the acceptor material in the second charge generation layer be 0.5% by mass or more, 1% by mass or more, 3% by mass or more, 5% by mass or more, or 10% by mass or more. In a tandem-type organic EL element, if the second charge generation layer contains a hole transport band material and an acceptor material, it is also preferable that the content of the hole transport band material in the second charge generation layer is more than 50% by mass, 60% or more by mass, 70% or more by mass, or 80% or more by mass. In a tandem-type organic EL element, the content of hole transport band material in the second charge generation layer is preferably 99.5% by mass or less, 99% by mass or less, 97% by mass or less, 95% by mass or less, or 90% by mass or less. The total content of acceptor material and hole transport band material in the second charge generation layer is preferably 100% by mass or less.
[0402] In a tandem organic EL device, the hole transport band material contained in the second charge generation layer and the hole transport band material contained in the layer within the hole transport band are either the same compound or different compounds.
[0403] In a tandem-type organic EL element, the first charge generation layer preferably contains an electron transport band material. The electron transport band material contained in the first charge generation layer and the electron transport band material contained in the layer within the electron transport band are either the same compound or different compounds. The first charge generation layer preferably contains at least one derivative selected from the group consisting of phenanthroline derivatives, imidazole derivatives, benzimidazole derivatives, azine derivatives, and carbazole derivatives.
[0404] In one embodiment of a tandem organic EL element, at least one layer selected from the group consisting of layers included in the charge generation unit may contain at least one selected from the group consisting of metals and metal compounds. In one embodiment of a tandem organic EL element, at least one layer selected from the group consisting of layers included in the charge generation unit may contain at least one selected from the group consisting of metals and metal compounds, and an electron transport band material. Examples of metals and metal compounds that the charge generation unit may contain are the same as examples of metals and metal compounds that the electron transport band may contain. It is preferable that the N-type charge generation layer in the charge generation unit contains at least one selected from the group consisting of the above-mentioned metals and metal compounds.
[0405] In a tandem organic EL element, it is preferable to have a charge generation unit positioned between the Xth stage light-emitting unit and the (X+1)th stage light-emitting unit, serving as a charge generation band. The charge generation unit is preferably positioned between the electron transport band included in the X-th stage light-emitting unit and the hole transport band included in the (X+1)-th stage light-emitting unit. In this case, the charge generation unit is preferably in direct contact with the electron transport band, preferably the charge generation layer in the charge generation unit is in direct contact with the electron transport layer or hole barrier layer in the electron transport band, and more preferably the first charge generation layer in the charge generation unit is in direct contact with the electron transport layer or hole barrier layer in the electron transport band. Furthermore, it is preferable that the charge generation unit is in direct contact with the hole transport band, that the charge generation layer in the charge generation unit is in direct contact with the hole transport layer or electron barrier layer in the hole transport band, and that the second charge generation layer in the charge generation unit is in direct contact with the hole transport layer or electron barrier layer in the hole transport band.
[0406] <Other configurations related to organic EL elements> Further details regarding the organic EL element according to this embodiment will be described.
[0407] (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.
[0408] (anode) In the organic EL element according to this embodiment, 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) for the anode. 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). 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. Among the layers formed on the anode, for example, the organic layer formed in contact with the anode (e.g., the hole injection layer) is formed using a composite material that allows for easy 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. 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.
[0409] When the organic EL element is of the bottom emission type, the anode is a light-transmitting electrode. The light-transmitting electrode is preferably formed of a metal material that is light-transmitting or semi-transmitting, allowing light emitted from the light-emitting layer to pass through. In this specification, light-transmitting or semi-transmitting means the property of transmitting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The light-transmitting or semi-transmitting metal material can be appropriately selected from the materials listed in the anode section above. The light-transmitting or semi-transmitting metal material may also be one of the materials listed below as materials to be used for the conductive layer (or transparent conductive layer).
[0410] When the organic EL element is of the top-emission type, the anode is a light-reflective electrode having a light-reflecting layer. The light-reflecting layer is preferably formed of a light-reflective metallic material. In this specification, light reflectivity means the property of reflecting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The light-reflective metallic material can be appropriately selected from the materials listed in the anode section. Examples of metallic materials used for the light-reflecting layer include: a single metal material selected from the group consisting of Al, Ag, Ta, Zn, Mo, W, Ni, and Cr, or an alloy material having one of these metals as the main component (preferably 50% by mass or more of the total); an amorphous alloy selected from the group consisting of NiP, NiB, CrP, and CrB; a microcrystalline alloy selected from the group consisting of NiAl and silver alloys, etc. Furthermore, as the metal material used for the light-reflecting layer, at least one alloy selected from the group consisting of APC (an alloy of silver, palladium, and copper), ARA (an alloy of silver, rubidium, and gold), MoCr (an alloy of molybdenum and chromium), and NiCr (an alloy of nickel and chromium) may be used. The light-reflecting layer may be a single layer or multiple layers.
[0411] The anode as a light-reflective electrode may consist only of a light-reflective layer, or it may be a multilayer structure having a light-reflective layer and a conductive layer (preferably a transparent conductive layer). When the anode is a multilayer structure having a light-reflective layer and a conductive layer, it is preferable that the conductive layer is placed between the reflective layer and the layer containing the hole transport band (e.g., a hole injection layer or a hole transport layer). Alternatively, the anode may be a multilayer structure in which a light-reflective layer is placed between two conductive layers (a first conductive layer and a second conductive layer). In such a multilayer structure, the first conductive layer and the second conductive layer may be formed of the same material or of different materials. In this specification, these multilayer structures may also be referred to as conductive material layers. The material used for the conductive layer can be appropriately selected from the materials listed in the anode section. Furthermore, for the conductive layer as a transparent electrode (transparent conductive layer), metals, alloys, electrically conductive compounds, and mixtures thereof with a large work function (specifically 4.0 eV or more) can be used. Furthermore, the conductive layer may also be made of, for example, alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca) and strontium (Sr), alloys containing at least one selected from the group consisting of alkali metals and alkaline earth metals (e.g., MgAg and AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing at least one selected from rare earth metals.
[0412] (cathode) In the organic EL element according to this embodiment, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof with a small work function (specifically, 3.8 eV or less) for the cathode. 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. 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. 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.
[0413] When the organic EL element is of the bottom emission type, the cathode is a light-reflective electrode. The light-reflective electrode is preferably formed from a light-reflective metallic material. The light-reflective metallic material can be appropriately selected from the materials listed in the cathode section. Alternatively, the light-reflective metallic material may be one of the materials listed above for use in the light-reflective layer.
[0414] When the organic EL element is of the top-emission type, the cathode is a light-transmitting electrode. The light-transmitting electrode is preferably made of a metal material that is light-transmitting or semi-transmitting, allowing light emitted from the light-emitting layer to pass through. Light-transmitting or semi-transmitting means the property of transmitting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The light-transmitting or semi-transmitting metal material can be appropriately selected from the materials listed in the cathode section above. The light-transmitting or semi-transmitting metal material may also be one of the materials listed above as materials used for the conductive layer (or transparent conductive layer).
[0415] (Capping layer) When an organic EL element is of the top-emission type, the organic EL element usually has a capping layer above the cathode. The capping layer may contain at least one compound selected from the group consisting of polymer compounds, metal oxides, metal fluorides, metal borides, silicon nitride, and silicon compounds (such as silicon oxide). Alternatively, the capping layer may contain at least one compound selected from the group consisting of aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, or dibenzofuran derivatives. Furthermore, a laminate in which layers containing these materials are stacked can also be used as a capping layer.
[0416] The organic EL element according to this embodiment may be a bottom-emission type organic EL element. Alternatively, the organic EL element may be a top-emission type organic EL element. When the organic EL element is of the bottom emission type, it is preferable that the anode is a light-transmitting electrode and the cathode is a light-reflecting electrode. When the organic EL element is of the top-emission type, it is preferable that the anode is a light-reflecting electrode with light-reflecting properties and the cathode is a light-transmitting electrode with light-transmitting properties.
[0417] (film thickness) The film thickness of each layer in the organic EL element according to 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 layer in the organic EL element is usually preferably in the range of a few nanometers to 1 μm.
[0418] (Emission wavelength of organic EL elements) In this embodiment, the organic EL element preferably emits light with a maximum peak wavelength of 500 nm or less when the element is driven, or emits light with a peak wavelength of 430 nm or more and 480 nm or less. The maximum peak wavelength of light emitted by the organic EL element during element operation is measured as follows: Current density is 10 mA / cm². 2The spectral radiance spectrum of an organic EL element is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) 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 maximum peak wavelength (unit: nm).
[0419] <Schematic configuration of an organic EL element> Figure 1 shows a schematic configuration of a first example of an organic EL element according to this embodiment. The organic EL element 101 shown in Figure 1 includes a light-transmitting substrate 2, an anode 3, a cathode 4, and a light-emitting unit 10 disposed between the anode 3 and the cathode 4. The light-emitting unit 10 includes, from the anode 3 side, a hole transport band 6, a light-emitting band 5, and an electron transport band 7 in that order. The hole transport band 6 includes, from the anode 3 side, a hole injection layer 61, a hole transport layer 62, and an electron barrier layer 63 in that order. The light-emitting band 5 includes a first light-emitting layer 51. The electron transport band 7 includes, from the anode 3 side, a hole barrier layer 71, an electron transport layer 72, and an electron injection layer 73 in that order. The organic EL element 101 shown in Figure 1 includes a charge transport band as a charge generation transport band, and includes a hole transport band 6 and an electron transport band 7 as charge transport bands. In Figure 1, the hole injection layer 61 is the first organic layer (first acceptor material containing layer), and the first light-emitting layer 51 contains the compound represented by formula (2) (first host material).
[0420] Figure 2 shows a schematic configuration of a second example of an organic EL element according to this embodiment. The organic EL element 101C shown in Figure 2 includes a light-transmitting substrate 2, an anode 3, a cathode 4, and a light-emitting unit 10C disposed between the anode 3 and the cathode 4. The light-emitting unit 10C is constructed by stacking a hole transport band 6, a light-emitting band 5A, and an electron transport band 7 in that order, starting from the anode 3 side. The organic EL element 101C is the same as the organic EL element 101 except that the light-emitting band 5C is different from the light-emitting band 5 in the organic EL element 101 of Figure 1. The light-emitting band 5C includes a first light-emitting layer 51 and a second light-emitting layer 52, starting from the anode 3 side. In the case of Figure 2, the hole injection layer 61 is the first organic layer (first acceptor material containing layer), and the first light-emitting layer 51 contains the compound represented by formula (2) (first host material).
[0421] The present invention is not limited to the configuration of the organic EL element shown in Figures 1 and 2. For example, in the organic EL element 101C, the light-emitting band 5C may be configured by stacking the second light-emitting layer 52 and the first light-emitting layer 51 in order from the anode 3 side.
[0422] Figure 3 shows a schematic configuration of a third example of an organic EL element according to this embodiment. The organic EL element 102 shown in Figure 3 includes a light-transmitting substrate 2, an anode 3, a cathode 4, a first-stage light-emitting unit 10A disposed between the anode 3 and the cathode 4, a second-stage light-emitting unit 10B, and a charge generation unit 8 as a charge generation band disposed between the light-emitting units 10A and 10B. The organic EL element 102 is a tandem type organic EL element. The first stage light-emitting unit 10A includes, from the anode 3 side, a hole transport band 6A, a light-emitting band 5A, and an electron transport band 7A, in that order. The hole transport band 6A includes, from the anode 3 side, a hole injection layer 611, a hole transport layer 621, and an electron barrier layer 631, in that order. The light-emitting band 5A includes the first light-emitting layer 511. The electron transport band 7A includes the hole barrier layer 711. The charge generation unit 8 includes a first charge generation layer 81 and a second charge generation layer 82 in that order, starting from the anode 3 side. The second stage light-emitting unit 10B includes, from the anode 3 side, a hole transport band 6B, a light-emitting band 5B, and an electron transport band 7B in that order. The hole transport band 6B includes, from the anode 3 side, a hole transport layer 622 and an electron barrier layer 632 in that order. The light-emitting band 5B includes a third light-emitting layer 512. The electron transport band 7B includes, from the anode 3 side, a hole barrier layer 712, an electron transport layer 722, and an electron injection layer 732 in that order. The organic EL element 102 shown in Figure 3 includes a charge transport band and a charge generation band as charge generation transport bands, and includes hole transport bands 6A, 6B and electron transport bands 7A, 7B as charge transport bands, and includes a charge generation unit 8 as a charge generation band. In the case of Figure 3, the hole injection layer 611 and the second charge generation layer 82 are the first organic layer (first acceptor material containing layer), and the first light-emitting layer 511 contains the compound represented by formula (2) (first host material). The third light-emitting layer 512 can be configured with the configuration of the first light-emitting layer or the second light-emitting layer described in the first embodiment. The third light-emitting layer 512 may also be a phosphorescent light-emitting layer.
[0423] Figure 4 shows a schematic configuration of a fourth example of an organic EL element according to this embodiment. The organic EL element 103 shown in Figure 4 includes a light-transmitting substrate 2, an anode 3, a cathode 4, a first-stage light-emitting unit 10D disposed between the anode 3 and the cathode 4, a second-stage light-emitting unit 10E, and a charge generation unit 8 as a charge generation band disposed between the light-emitting unit 10D and the light-emitting unit 10E. The organic EL element 103 is a tandem type organic EL element. The organic EL element 103 shown in Figure 4 differs from the organic EL element 102 shown in Figure 3 in the configuration of its first and second stage light-emitting units. The first stage light-emitting bandwidth 5D of the organic EL element 103 differs from the first stage light-emitting bandwidth 5A of the organic EL element 102, and the second stage light-emitting bandwidth 5E of the organic EL element 103 differs from the second stage light-emitting bandwidth 5B of the organic EL element 102. Aside from these differences, the organic EL element 103 has the same configuration as the organic EL element 102 shown in Figure 3. The first stage light emission band 5D includes, in order from the anode 3 side, the first light emission layer 511 and the second light emission layer 521. The second stage light emission band 5E includes, in order from the anode 3 side, the third light emission layer 512 and the fourth light emission layer 522. In the case of Figure 4, the hole injection layer 611 and the second charge generation layer 82 are the first organic layer (first acceptor material containing layer), and the first light-emitting layer 511 contains the compound represented by formula (2) (first host material). The second light-emitting layer 521 is the second light-emitting layer described in the first embodiment. The third light-emitting layer 512 and the fourth light-emitting layer 522 can, for example, be configured with the first light-emitting layer and the second light-emitting layer described in the first embodiment, respectively. The third light-emitting layer 512 may be a phosphorescent light-emitting layer, or it may contain a compound represented by formula (2) (first host material). The fourth light-emitting layer 522 may be a phosphorescent light-emitting layer, or it may contain a compound represented by formula (2) (first host material).
[0424] The present invention is not limited to the configuration of the tandem organic EL element shown in Figures 3 and 4. For example, in Figures 3 and 4, one of the hole injection layer 611 and the second charge generation layer 82 may be the first organic layer (first acceptor material containing layer). For example, in Figure 3, the configuration may be one in which the first light-emitting band 5A and the second light-emitting band 5B are swapped. In Figure 4, the configuration may be one in which the first light-emitting band 5D and the second light-emitting band 5E are swapped. In Figure 4, the first light-emitting band 5D may be a configuration in which the second light-emitting layer 521 and the first light-emitting layer 511 are stacked in order from the anode 3 side.
[0425] <Layer formation method> The method for forming each layer of the organic EL element according to this embodiment is not limited to those specifically mentioned above, but each layer of the organic EL element can be formed independently by selecting from known methods such as dry deposition and wet deposition. Examples of dry deposition methods include vacuum deposition, sputtering, plasma deposition, and ion plating. Examples of wet deposition methods include spin coating, dipping, flow coating, and inkjet deposition.
[0426] In the organic EL element according to this embodiment, the layer containing multiple types of substances can be formed by co-evaporation using multiple types of compounds, etc., by evaporation using a pre-mixed mixture of multiple types of compounds, etc., or by coating using a pre-mixed mixture of multiple types of compounds, etc. The pre-mixed mixture of multiple types of compounds may be in powder form. The pre-mixed mixture of multiple types of compounds may be in solution form. The method of pre-mixing multiple types of compounds, etc., is sometimes referred to as premixing. The method of premixing is not particularly limited, but for example, the evaporation ratio of the compounds constituting the premixed mixture can be adjusted by adjusting the substituents of the compounds constituting the mixture to adjust the molecular weight of the compounds, or by adjusting the mixing ratio.
[0427] [Explanation of various materials] Examples of various materials that can be used in the organic EL element according to this embodiment are described below.
[0428] <Hole transport zone materials> The hole transport band material is preferably a material that can be used in layers that may be included in the hole transport band (for example, a hole injection layer, a hole transport layer, or an electron barrier layer). Alternatively, the hole transport band material may be used in layers included in the charge generation band.
[0429] (Compounds represented by formula (B1) or formula (B2)) In the organic EL element according to this embodiment, the hole transport band material is also preferably a compound represented by the following formula (B1) or formula (B2).
[0430] [ka]
[0431] (In the above formula (B1), L 11 , L 12 and L 13 Each of them operates independently. single bond, Substituted or unsubstituted ring-forming arylene groups with 6 to 50 carbon atoms, A substituted or unsubstituted divalent heterocyclic group with 5 to 50 ring-forming atoms, or A divalent group formed by the bonding of two groups selected from the group consisting of a substituted or unsubstituted arylene group with 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted divalent heterocyclic group with 5 to 50 ring-forming atoms. A1, B1, and C1 are each independent of each other. 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 -Si(R 121 )(R 122 )(R 123 It is a base represented by ), R 121 , R 122 and R 123 These are, independently, substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms. R 121 If multiple R 121 They are either identical or different from one another. R 122 If multiple R 122 They are either identical or different from one another. R 123 If multiple R 123 They are either identical or different to one another.
[0432] [ka]
[0433] (In the above formula (B2), L C1 , L C2 , L C3 and L C4 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, n2 is 1, 2, 3, or 4. If n2 is 1, L C5 teeth, 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, If n2 is 2, 3, or 4, then multiple L C5 They are either identical or different from one another. If n2 is 2, 3, or 4, then multiple L C5 teeth, They combine with each other to form a substituted or unsubstituted monoring, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, L that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring C5 teeth, 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 131 Ar 132 Ar 133 and Ar 134 Each of them operates independently. 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 -Si(R 121 )(R 122 )(R 123 It is a base represented by ), R 121 , R 122 and R 123 These are, independently, substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms. R 121 If multiple R 121 They are either identical or different from one another. R 122If multiple R 122 They are either identical or different from one another. R 123 If multiple R 123 They are either identical or different to one another.
[0434] In the organic EL element according to this embodiment, it is also preferable that the first amino group represented by the following formula (B2-1) and the second amino group represented by the following formula (B2-2) in the compound represented by formula (B2) are the same group.
[0435] [ka]
[0436] (In the above formulas (B2-1) and (B2-2), * represents L C5 This is the bonding position.
[0437] In the organic EL element according to this embodiment, the first amino group represented by formula (B2-1) and the second amino group represented by formula (B2-2) may be different groups from each other.
[0438] In the organic EL element according to this embodiment, A1, B1, and C1 in formula (B1) and the following formula (B100) are preferably groups that are independently represented by any of the following formulas selected from the group consisting of (1A), (1B), (1C), (1D), (1E), (1F), and (1G).
[0439] [ka]
[0440] (In the above formula (1A), *11 is L 11 , L 12 or L 13 This is the binding position to, R 101 ~R 105One of the selected is a single bond that connects to *12, R 106 ~R 110 One of the selected is a single bond that connects to *13, R that is not a single bond 101 ~R 105 and R 106 ~R 110 Each of these is independently a hydrogen atom, an unsubstituted C1-C10 alkyl group, or an unsubstituted ring-forming C6-C12 aryl group. R that is not a single bond 101 ~R 105 Of the pairs of adjacent elements, none of them are connected to each other. R that is not a single bond 106 ~R 110 Of the pairs of adjacent elements, none of them are connected to each other. R 111 ~R 115 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heterocyclic group. R 111 ~R 115 Of the pairs of adjacent elements, none of them are connected to each other. m is 0, 1, or 2, and n is 0 or 1. When m=0 and n=0, *13 is L 11 , L 12 or L 13 This is the binding position to, When m=0 and n=1, *12 is L 11 , L 12 or L 13 This is the binding position to, When m=1 and n=0, R 101 ~R 105 One of the bonds selected is a single bond that connects to *13.
[0441] [ka]
[0442] (In the above formula (1B), *14 is L 11 , L 12 or L 13 This is the binding position to, R 121 ~R 128 One of the selected is a single bond that connects to *15, R that is not a single bond 121 ~R 128 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted ring-forming C6-C12 aryl group. R that is not a single bond 121 ~R 128 (Of these, no two or more adjacent pairs are connected to each other.)
[0443] [ka]
[0444] (In the above formula (1C), *16 is L 11 , L 12 or L 13 This is the binding position to, R 131 ~R 140 One of the selected is a single bond that connects to *17, R that is not a single bond 131 ~R 140 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted ring-forming C6-C12 aryl group. R that is not a single bond 131 ~R 140 (Of these, no two or more adjacent pairs are connected to each other.)
[0445] [ka]
[0446] (In the above formula (1D), *18 is L 11 , L 12 or L 13 This is the binding position to, X 11 is an oxygen atom, a sulfur atom, C(Ra)(Rb) or N(Rc), A pair consisting of Ra and Rb 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, n is either 0 or 1. When n is 0, R 141 ~R 148 One selected from Rc, and Ra and Rb, which do not form the substituted or unsubstituted monoring and do not form the substituted or unsubstituted fused ring, is a single bond bonded to *19. When n is 1, R 141 and R 142 One of them is a single bond that connects to *a, and R 141 and R 142 Is the other one a single bond that connects to *b? R 142 and R 143 One of them is a single bond that connects to *a, and R 142 and R 143 The other side is a single bond that connects to *b, or R 143 and R 144 One of them is a single bond that connects to *a, and R 143 and R 144 The other side is a single bond that connects to *b, (i)R 145 ~R 148 , R 14A , R 14B , R 14C , R 14D and Rc, and (ii) R that is not a single bond to *a and *b 141 ~R 144And, (iii) one selected from the group consisting of Ra and Rb that are not single bonds bonded to *a and *b, and that do not form the substituted or unsubstituted monoring and do not form the substituted or unsubstituted fused ring is a single bond bonded to *19, R, which is not a single bond, is bonded to the aforementioned *19. 141 ~R 148 , R 14A , R 14B , R 14C , R 14D And Rc, and Ra and Rb, which are not single bonds bonded to *19 and do not form the substituted or unsubstituted monorings, nor do they form the substituted or unsubstituted fused rings, are each independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming heteroaryl group with 5-13 atoms.
[0447] [ka]
[0448] (In the above formula (1E), *11a is L 11 , L 12 or L 13 This is the binding position to, R 151 ~R 155 One of the selected is a single bond that connects to *11b, R 151 ~R 155 Another one selected from among them is a single bond that connects to *11c, R that is not a single bond 151 ~R 155 These are, independently, a hydrogen atom, an unsubstituted C1-C10 alkyl group, or an unsubstituted phenyl group. R that is not a single bond 151 ~R 155 Of the pairs of adjacent elements, none of them are connected to each other. R 161 ~R 165 and R 171 ~R 175Each of these is independently either a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms.
[0449] [ka]
[0450] (In the above formula (1F), *11d is L 11 , L 12 or L 13 This is the binding position to, R 181 ~R 192 One of the selected is a single bond that joins *11e, R that is not a single bond 181 ~R 192 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted ring-forming C6-C12 aryl group. R that is not a single bond 181 ~R 192 (None of the pairs of adjacent elements are connected to each other.)
[0451] [ka]
[0452] (In the above formula (1G), X B It consists of a single bond, an oxygen atom, a sulfur atom, and N(R) B11 ) or C(R B12 )(R B13 ) and X B If there are multiple X B They are either identical or different from one another. X B is C(R B12 )(R B13 ) If R B12 and R B13 A set consisting of They combine with each other to form a monoring, either substituted or unsubstituted, Combine with each other to form a substituted or unsubstituted fused ring, or Do not combine with each other, R B1 、R B2 、R B3 、R B4 、R B5 、R B6 、R B7 、R B8 、R B9 、R B10 、R B11 、R B12 and R B13 one of them is a single bond connecting to *1, R that is not a single bond connecting to *1 B1 、R B2 、R B3 、R B4 、R B5 、R B6 、R B7 、R B8 and R B11 are each independently a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 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, 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 B9 and R B10 the group consisting of[[ID=8--]] combine with each other to form a substituted or unsubstituted monocyclic ring, combine with each other to form a substituted or unsubstituted fused ring, or do not combine with each other, *1 is not a single bond, and does not form the aforementioned substituted or unsubstituted monoring, nor does it form the aforementioned substituted or unsubstituted fused ring. B9 , R B10 , R B12 and R B13 Each of them operates independently. 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 with 6 to 50 carbon atoms, *2 is L 11 , L 12 or L 13 This is the bonding position. (In the base represented by the above formula (1G), R 901 , R 902 , R 903 and R 904 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, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group, R 901 If multiple R 901 They are either identical or different from each other, R 902 If multiple R 902 They are either identical or different from each other, R 903 If multiple R 903 They are either identical or different from each other, R 904 If multiple R 904 They are either identical or different to one another.
[0453] In the organic EL element according to this embodiment, the hole transport band material is preferably a compound represented by the following formula (B100).
[0454] [ka]
[0455] (In the above formula (B100), L 11 , L 12 and L 13 Each of them operates independently. single bond, Substituted or unsubstituted ring-forming arylene groups with 6 to 50 carbon atoms, A substituted or unsubstituted divalent heterocyclic group with 5 to 50 ring-forming atoms, or A divalent group formed by the bonding of two groups selected from the group consisting of a substituted or unsubstituted arylene group with 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted divalent heterocyclic group with 5 to 50 ring-forming atoms. A1, B1, and C1 are each independent of each other. 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, -Si(R C1 )(R C2 )(R C3 A base represented by ) or The group is represented by the above formula (1G), However, at least one selected from the group consisting of A1, B1, and C1 is a group represented by formula (1G), R C1 , R C2 and R C3 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 C1 If multiple R C1 They are either identical or different from one another. R C2 If multiple R C2 They are either identical or different from one another. R C3When there are a plurality of R, the plurality of R C3 are the same as or different from each other, in the formula (1G), X B is a single bond, an oxygen atom, a sulfur atom, N(R B11 ), or C(R B12 )(R B13 ), and X B when there are a plurality of X, the plurality of X B are the same as or different from each other, X B when is C(R B12 )(R B13 ), the group consisting of R B12 and R B13 either combines with each other to form a substituted or unsubstituted monocyclic ring, combines with each other to form a substituted or unsubstituted condensed ring, or does not combine with each other, and one of R R B1 、R B2 、R B3 、R B4 、R B5 、R B6 [[ID=5,2]]、R B7 、R B8 、R B9 、R B10 、R B11 、R B12 and R B13 is a single bond connecting to *1, R<B B1 、R B2 、R B3 、R B4 、R B5 、R B6 、R[[ID=8,1]] B7 、R B8 and R B11 are each independently a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 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 A base represented by ) -O-(R 904 A base represented by ) 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 B9 and R B10 A group consisting of, 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, *1 is not a single bond, and does not form the aforementioned substituted or unsubstituted monoring, nor does it form the aforementioned substituted or unsubstituted fused ring. B9 , R B10 , R B12 and R B13 Each of them operates independently. 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 with 6 to 50 carbon atoms, *2 is L 11 , L 12 or L 13 This is the bonding position with, If there are two or more groups represented by formula (1G), then the two or more groups represented by formula (1G) are either identical or different from each other. (In the compound represented by the above formula (B100), R 901 , R 902 , R 903 and R 904 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 to one another.
[0456] In the organic EL element according to this embodiment, the group represented by formula (1G) is preferably a group represented by any of the formulas selected from the group consisting of formulas (11G), (12G), and (13G).
[0457] [ka]
[0458] [ka]
[0459] (In the above formulas (11G), (12G), or (13G), X B , R B1 , R B2 , R B3 , R B4 , R B5 , R B6 , R B7 , R B8 *1 and *2 are X in the above formula (1G), respectively. B , R B1 , R B2 , R B3 , R B4 , RB5 , R B6 , R B7 , R B8 , is synonymous with *1 and *2, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 Each of them operates independently. hydrogen atom, Cyano group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkyl halides 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 A base represented by ) -O-(R 904 A base represented by ) 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. Z is an oxygen atom, a sulfur atom, or C(R) Z1 )(R Z2 ) and R Z1 and R Z2 Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 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.)
[0460] In the organic EL element according to this embodiment, X in formulas (1G), (11G), (12G), and (13G) B It is preferable that it is a single bond or an oxygen atom.
[0461] In the organic EL element according to this embodiment, the group represented by formula (1G) is preferably a group represented by any of the following formulas selected from the group consisting of (11G-1), (12G-1), (12G-2), and (13G-1).
[0462] [ka]
[0463] [ka]
[0464] (In the above formulas (11G-1), (12G-1), (12G-2), or (13G-1), R B1 , R B2 , R B3 , R B4 , R B5 , R B6 , R B7 , R B8 *1 and *2 are R in formula (1G) above, respectively. B1 , R B2 , R B3 , R B4 , R B5 , R B6 , R B7 , R B8 , is synonymous with *1 and *2, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 Each of them operates independently. hydrogen atom, Cyano group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkyl halides 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 A base represented by ) -O-(R 904 A base represented by ) 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.
[0465] In the above formulas (11G), (12G), (13G), (11G-1), (12G-1), (12G-2), and (13G-1), R 11 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 20 This is a hydrogen atom. In the above formulas (11G), (12G), (13G), (11G-1), (12G-1), (12G-2), and (13G-1), R 12 and R 19 Each of these is independently a substituent other than a hydrogen atom. In the above formulas (11G), (12G), (13G), (11G-1), (12G-1), (12G-2), and (13G-1), R 11 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 20 is a hydrogen atom, and R 12 and R 19 Each of these is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms.
[0466] In the organic EL element according to this embodiment, when n is 1 in formula (1D), R 141 and R 142 One of them is a single bond that connects to *a, and R 141 and R142 If the other bond is a single bond to *b, then equation (1D) can be expressed as equation (13D) below, R 142 and R 143 One of them is a single bond that connects to *a, and R 142 and R 143 If the other bond is a single bond to *b, then equation (1D) can be expressed as equation (12D) below, R 143 and R 144 One of them is a single bond that connects to *a, and R 143 and R 144 If the other bond is a single bond to *b, then formula (1D) is preferably represented by the following formula (11D).
[0467] In the organic EL element according to this embodiment, it is preferable that at least one selected from the group consisting of A1, B1, and C1 in formula (B1) or formula (B100) is a group represented by any of the following formulas selected from the group consisting of (11D), (12D), and (13D).
[0468] [ka]
[0469] [ka]
[0470] [ka]
[0471] (In the above formulas (11D), (12D), and (13D), *18 is L 11 , L 12 or L 13 This is the binding position to, X 11 This is X in equation (1D) above. 11 It is synonymous with, (iv)R 141 ~R148 , R 14A , R 14B , R 14C , R 14D And Rc, and one selected from the group consisting of (v) Ra and Rb that do not form the substituted or unsubstituted monoring and do not form the substituted or unsubstituted fused ring is a single bond bonded to *19, R, which is not a single bond, is bonded to the aforementioned *19. 141 ~R 148 , R 14A , R 14B , R 14C , R 14D And Rc, and Ra and Rb, which are not single bonds bonded to *19 and do not form the substituted or unsubstituted monorings, nor do they form the substituted or unsubstituted fused rings, are each independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming heteroaryl group with 5-13 atoms.
[0472] In the organic EL element according to this embodiment, R in formula (11D) 148 It is preferable that the bond to *19 is a single bond.
[0473] In the organic EL element according to this embodiment, X in formula (11D) 11 It is preferable that it is an oxygen atom.
[0474] In the organic EL element according to this embodiment, it is preferable that n in formula (1D) is 0.
[0475] In the organic EL element according to this embodiment, it is preferable that at least one selected from the group consisting of A1, B1, and C1 in formula (B1) or formula (B100) is a group represented by any of the following formulas selected from the group consisting of (14D), (15D), (16D), and (17D).
[0476] [ka]
[0477] [ka]
[0478] [ka]
[0479] [ka]
[0480] (In the above formulas (14D), (15D), (16D), and (17D), *18 is L 11 , L 12 or L 13 This is the binding position to, (vi)R 141 ~R 148 And Rc, and (vii) Ra and Rb which do not form the substituted or unsubstituted monoring and which do not form the substituted or unsubstituted fused ring, one selected from the group is a single bond bonded to *19, R, which is not a single bond, is bonded to the aforementioned *19. 141 ~R 148 And Rc, and Ra and Rb, which are not single bonds bonded to *19 and do not form the substituted or unsubstituted monorings, nor do they form the substituted or unsubstituted fused rings, are each independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming heteroaryl group with 5-13 atoms.
[0481] In the organic EL element according to this embodiment, R in formula (14D) 141 , R 144 , R 145 , or R 148 It is preferable that the bond to *19 is a single bond.
[0482] In the organic EL element according to this embodiment, it is preferable that Rc in formula (15D) is a single bond coupled to *19.
[0483] In the organic EL element according to this embodiment, L in formula (B1) or (B100) 11 , L 12 and L 13 Each of these is preferably a single bond or a group represented by the following formulas (L1), (L2), (L3), (L4), (L5), (L6), (L7), (L8), (L9), or (L10).
[0484] [ka]
[0485] In the above formulas (L1) to (L10), * indicates a bond position. Each of the groups represented by the above formulas (L1) to (L10) may or may not have one or more of the above-mentioned "any substituents". Each of the groups represented by the above formulas (L1) to (L10) may independently have one or more deuterium atoms.
[0486] In the organic EL element according to this embodiment, L 11 If it is a single bond, A1 is directly bonded to the amino group nitrogen atom in formula (B1) or (B100), L 12 If it is a single bond, B1 is directly bonded to the amino group nitrogen atom in formula (B1) or (B100), L 13 When C1 is a single bond, it is preferable that C1 is directly bonded to the amino group nitrogen atom in formula (B1) or (B100).
[0487] In the organic EL element according to this embodiment, the hole transport band material is preferably a compound represented independently by the following formulas (B10), (B11), (B12), (B13), (B14), or (B15).
[0488] [ka]
[0489] [ka]
[0490] [ka]
[0491] (In the above formulas (B10), (B11), (B12), (B13), (B14), and (B15), L 11 , L 12 , L 13 A1, B1, and C1 are, respectively, L in formula (B1) or (B100). 11 , L 12 , L 13 This is synonymous with A1, B1, and C1. R1, R2, R3, and R4 each operate independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 13 carbon atoms, or A heteroaryl group having 5 to 13 substituted or unsubstituted ring-forming atoms, The four R1s are either identical or different from each other. The four R2s are either identical or different from each other. The four R3s are either identical or different from each other. The four R4s are either identical or different from one another.
[0492] In the organic EL element according to this embodiment, the hole transport band material is preferably a compound represented independently by the following formulas (B16), (B17), (B18), (B19), or (B20).
[0493] [ka]
[0494] [ka]
[0495] (In the above formulas (B16), (B17), (B18), (B19), and (B20), A1, B1, and C1 are equivalent to A1, B1, and C1 in the above formula (B1) or (B100), respectively. R1, R2, R3, and R4 are each independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C6-C13 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heteroaryl group. The four R1s are either identical or different from each other, the four R2s are either identical or different from each other, the four R3s are either identical or different from each other, and the four R4s are either identical or different from each other.
[0496] In the organic EL element according to this embodiment, it is preferable that R1, R2, and R3 in the hole transport band material are deuterium atoms.
[0497] In the organic EL element according to this embodiment, it is preferable that at least one selected from the group consisting of A1, B1, and C1 in formulas (B1), (B100), (B10), (B11), (B12), (B13), (B14), (B15), (B16), (B17), (B18), (B19), and (B20) includes at least one group selected from the group consisting of groups represented by formulas (1A) and (1B). Hereinafter, "(B10), (B11), (B12), (B13), (B14), (B15), (B16), (B17), (B18), (B19), and (B20)" may be abbreviated as "(B10) to (B20)".
[0498] In the organic EL element according to this embodiment, it is preferable that one selected from the group consisting of A1, B1, and C1 in formulas (B1), (B10) to (B20) includes at least one group selected from the group consisting of groups represented by formulas (1A) and (1B), and the remaining two selected from the group consisting of A1, B1, and C1 include at least one group selected from the group consisting of groups represented by formulas (1D), (11D), (12D), (13D), (14D), (15D), (16D), and (17D).
[0499] In the organic EL element according to this embodiment, it is preferable that two selected from the group consisting of A1, B1, and C1 in formulas (B1), (B100), and (B10) to (B20) include at least one group selected from the group consisting of groups represented by formulas (1A) and (1B).
[0500] In the organic EL element according to this embodiment, it is preferable that two selected from the group consisting of A1, B1, and C1 in formulas (B1), (B10) to (B20) include at least one group selected from the group consisting of groups represented by formulas (1A) and (1B), and the remaining one selected from the group consisting of A1, B1, and C1 each independently includes at least one group selected from the group consisting of groups represented by formulas (1D), (11D), (12D), (13D), (14D), (15D), (16D), and (17D).
[0501] In the organic EL element according to this embodiment, at least one selected from the group consisting of A1, B1, and C1 in formulas (B1), (B100), (B10) to (B20) is a group represented by formula (1G), and X B It is preferable that it is an oxygen atom.
[0502] In the organic EL element according to this embodiment, two selected from the group consisting of A1, B1, and C1 in formulas (B1), (B100), (B10) to (B20) are groups represented by formula (1G), and X B It is preferable that it is an oxygen atom.
[0503] In the organic EL element according to this embodiment, it is preferable that at least one selected from the group consisting of A1, B1, and C1 in formulas (B1), (B100), (B10) to (B20) includes at least one group selected from the group consisting of groups represented by formulas (11G), (12G), and (13G).
[0504] In the organic EL element according to this embodiment, it is preferable that two selected from the group consisting of A1, B1, and C1 in formulas (B1), (B100), (B10) to (B20) include at least one group selected from the group consisting of groups represented by formulas (11G), (12G), and (13G).
[0505] In the organic EL element according to this embodiment, it is preferable that at least one selected from the group consisting of A1, B1, and C1 in formulas (B1), (B100), (B10) to (B20) includes at least one group selected from the group consisting of groups represented by formulas (11G-1), (12G-1), (12G-2), and (13G-1).
[0506] In the organic EL element according to this embodiment, it is preferable that two selected from the group consisting of A1, B1, and C1 in formulas (B1), (B100), (B10) to (B20) include at least one group selected from the group consisting of groups represented by formulas (11G-1), (12G-1), (12G-2), and (13G-1).
[0507] In the organic EL element according to this embodiment, it is preferable that at least one selected from the group consisting of A1, B1, and C1 in formulas (B1), (B100), (B10) to (B20) has one or more substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms (preferably 1 to 6 carbon atoms) as substituents.
[0508] In the organic EL element according to this embodiment, it is preferable that at least one selected from the group consisting of A1, B1, and C1 in formulas (B1), (B100), (B10) to (B20) has one or more alkyl groups including branched chains as substituents.
[0509] In the organic EL element according to this embodiment, it is preferable that at least one selected from the group consisting of A1, B1, and C1 in formulas (B1), (B100), (B10) to (B20) has one or more tert-butyl groups as substituents.
[0510] In the organic EL element according to this embodiment, the hole transport band material is independently, A monoamine compound having one substituted or unsubstituted amino group in the molecule. Diamine compounds having two substituted or unsubstituted amino groups in the molecule, Triamine compounds having three substituted or unsubstituted amino groups in the molecule, and It is preferable that the compound is at least one amine compound selected from the group consisting of tetraamine compounds having four substituted or unsubstituted amino groups in the molecule.
[0511] In the organic EL element according to this embodiment, the hole transport band material is preferably a monoamine compound or a diamine compound, independently of each other.
[0512] In the organic EL element according to this embodiment, the hole transport band material is independently a monoamine compound.
[0513] In hole transport band materials, the substituents in the phrase "substituted or unsubstituted" are preferably, independently, a halogen atom, an unsubstituted C1-C25 alkyl group, an unsubstituted ring-forming C6-C25 aryl group, or an unsubstituted ring-forming C5-C5 heterocyclic group.
[0514] In hole transport band materials, the substituents in the phrase "substituted or unsubstituted" are preferably, independently, an unsubstituted C1-C6 alkyl group, an unsubstituted ring-forming C6-C13 aryl group, or an unsubstituted ring-forming C5-C13 heterocyclic group.
[0515] In hole transport band materials, the substituents in the phrase "substituted or unsubstituted" are preferably, independently, an unsubstituted C1-C6 alkyl group, an unsubstituted ring-forming C6-C12 aryl group, or an unsubstituted ring-forming C5-C10 heterocyclic group.
[0516] In hole transport band materials, it is also preferable that any groups described as "substituted or unsubstituted" are all "unsubstituted" groups.
[0517] (Method for manufacturing hole transport zone materials) Hole transport zone materials can be manufactured by known methods. Furthermore, hole transport zone materials can also be manufactured by following known methods and using known alternative reactions and raw materials tailored to the target material.
[0518] (Specific examples of hole transport zone materials) Specific examples of hole transport zone materials include the following compounds. However, the present invention is not limited to these specific examples.
[0519] [ka]
[0520] [ka]
[0521] [ka]
[0522] [ka]
[0523]
change
[0524]
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[0525]
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[0526]
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[0527]
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[0528]
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[0529]
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[0530]
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[0531]
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[0532]
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[0533] [ka]
[0534] [ka]
[0535] [ka]
[0536] <Second Acceptor Material> In the organic EL element according to this embodiment, the second acceptor material is given by the following formula (P11) It is preferable to include at least one of the first ring structure represented by the formula (P12) below and the second ring structure represented by the formula (P12) below.
[0537] [ka]
[0538] (The first ring structure represented by formula (P11) is condensed in the molecule of the second acceptor material with at least one of the ring structures of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted heterocycle having 5 to 50 ring-forming atoms.) = Z 10 The structure represented by (P11a), (P11b), (P11c), (P11d), (P11e), (P11f), (P11g), (P11h), (P11i), (P11j), (P11k), or (P11m) is represented by the following formulas:
[0539] [ka]
[0540] [ka]
[0541] (In the above formulas (P11a), (P11b), (P11c), (P11d), (P11e), (P11f), (P11g), (P11h), (P11i), (P11j), (P11k), or (P11m), R 11 ~R 14 R 111 ~R 120 Each of them operates independently. hydrogen atom, halogen atom, Hydroxyl group, Cyano group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkyl halides 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 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 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.
[0542] (In the above formula (P12), Z1 to Z5 are each independent of each other.) Nitrogen atom, R 15 A carbon atom that bonds with it, or The carbon atom that bonds with other atoms in the molecule of the second acceptor material, Of Z1 to Z5, at least one is a carbon atom that bonds with other atoms in the molecule of the second acceptor material. R 15 teeth, hydrogen atom, halogen atom, Cyano group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, 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, -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 alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, Carboxy group, Substituted or unsubstituted ester groups, Substituted or unsubstituted carbamoyl groups, Nitro group, and Selected from the group consisting of substituted or unsubstituted siloxanil groups, R 15 If multiple R 15 They are either identical or different.
[0543] (In the second acceptor material, R 901 ~R 907 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, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group. R 901 If there are multiple R 901 They are either identical or different from one another. R 902 If there are multiple R902 They are either identical or different from one another. R 903 If there are multiple R 903 They are either identical or different from one another. R 904 If there are multiple R 904 They are either identical or different from one another. R 905 If there are multiple R 905 They are either identical or different from one another. R 906 If there are multiple R 906 They are either identical or different from one another. R 907 If there are multiple R 907 They are either identical or different to one another.
[0544] In the organic EL element according to this embodiment, the second acceptor material is preferably a condensation compound formed by the condensation of two or three structures represented by the following formula (P13) into the third ring structure. The third ring structure is selected from substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 ring-forming carbon atoms and substituted or unsubstituted heterocycles having 5 to 50 ring-forming atoms.
[0545] [ka]
[0546] (In the above formula (P13), Ac3 is a ring structure that condenses with the aforementioned third ring structure, and is represented by the above formula (P11). Xa and Xb are each independently of C(R 16 ) or nitrogen atoms, and multiple R 16 They are either identical or different from one another. R 16 , R 17 and R 18Each of these independently consists of a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C1-C50 halogenated alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, 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 The group is represented by ), 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.
[0547] The second acceptor material is preferably a compound represented by the following formula (P14) or formula (P15).
[0548] [ka]
[0549] [ka]
[0550] (In the above formulas (P14) and (P15), Ar1 is a substituted or unsubstituted aromatic hydrocarbon ring with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle with 5 to 50 ring-forming atoms. a1, a2, and a3 are each independently first ring structures represented by the formula (P11), X 13 , X 14 , X 15 , X 16 , X 17 and X 18 These are, independently, equivalent to Xa and Xb in the above formula (P13), R 141 , R 142 , R 143 , R 144, R 145 and R 146 Each of these independently corresponds to R in equation (P13) above. 17 and R 18 (This is synonymous with...)
[0551] In the second acceptor material, Ar1 in formulas (P14) and (P15) is preferably a substituted or unsubstituted benzene ring, or a substituted or unsubstituted heterocycle with 6 ring-forming atoms.
[0552] The second acceptor material is preferably represented by the following formula (P14A) or formula (P15A).
[0553] [ka]
[0554] [ka]
[0555] (In the above formulas (P14A) and (P15A), a1, a2, and a3 are each independently first ring structures represented by the formula (P11), X 13 , X 14 , X 15 , X 16 , X 17 and X 18 These are, independently, equivalent to Xa and Xb in equation (13) above, R 141 , R 142 , R 143 , R 144 , R 145 and R 146 Each of these independently corresponds to R in equation (P13) above. 17 and R 18 It is synonymous with [the above]. In the above formula (P14A), Z 11 and Z 12 Each of these is independently either a CH atom or a nitrogen atom.
[0556] In the second acceptor material, R in formula (P13) 17 and R 18 Preferably, at least one of these is a fluorine atom, a fluoroalkyl group, a fluoroalkoxy group, or a cyano group.
[0557] The second acceptor material is preferably a compound represented by any of the following formulas (P141) to (P144) and formula (P151).
[0558] [ka]
[0559] [ka]
[0560] (In the above equations (P141) to (P144) and equation (P151), R 141 , R 143 , R 144 and R 146 These are, independently, a fluorine atom, a fluoroalkyl group, a fluoroalkoxy group, or a cyano group.
[0561] The second acceptor material is also preferably a compound represented by formula (P143).
[0562] The second acceptor material is also preferably a compound represented by any of the following formulas (P145) to (P148) and formula (P152).
[0563] [ka]
[0564] [ka]
[0565] (In the above equations (P145) to (P148) and equation (P152), Ar 141 Ar 143 Ar 144 and Ar 146 Each of them operates independently. A ring-forming aromatic hydrocarbon group having 6 to 30 carbon atoms, having at least one substituent selected from the group consisting of a fluorine atom, a fluoroalkyl group, a fluoroalkoxy group, and a cyano group, or It is a heterocyclic group having 5 to 30 ring-forming atoms, having at least one substituent selected from the group consisting of a fluorine atom, a fluoroalkyl group, a fluoroalkoxy group, and a cyano group.
[0566] The second acceptor material is also preferably a compound represented by any of the following formulas (P1451), (P1461), (P1471), and (P1481).
[0567] [ka]
[0568] [ka]
[0569] [ka]
[0570] [ka]
[0571] (R in the above formula (P1451) 1451 ~R 1460 , R in the above formula (P1461) 1461 ~R 1470 , R in the above formula (P1471) 1471 ~R 1480 , and R in formula (P1481) 1481 ~R 1490Each of these is independently a hydrogen atom, a fluorine atom, a fluoroalkyl group, a fluoroalkoxy group, or a cyano group. R 1451 ~R 1460 One or more of them are a fluorine atom, a fluoroalkyl group, a fluoroalkoxy group, or a cyano group. R 1461 ~R 1470 One or more of them are a fluorine atom, a fluoroalkyl group, a fluoroalkoxy group, or a cyano group. R 1471 ~R 1480 One or more of them are a fluorine atom, a fluoroalkyl group, a fluoroalkoxy group, or a cyano group. R 1481 ~R 1490 One or more of the components are a fluorine atom, a fluoroalkyl group, a fluoroalkoxy group, or a cyano group.
[0572] The second acceptor material is also preferably a compound represented by formula (P1451).
[0573] The second acceptor material is also preferably a compound represented by the formula (P1461).
[0574] The second acceptor material may also preferably be a compound represented by the following formula (P16) or formula (P17).
[0575] [ka]
[0576] [ka]
[0577] (In the above formulas (P16) and (P17), X 13 , X 14 , X 15 and X 16These are, independently, equivalent to Xa and Xb in the above formula (P13), R 141 , R 142 , R 143 and R 144 Each of these independently corresponds to R in equation (P13) above. 17 and R 18 It is synonymous with, a1 and a2 are each independently first ring structures represented by formula (P11), b1 is a ring structure represented by the following formula (P17A).
[0578] [ka]
[0579] (In the above formula (P17A), X 19 (This is either a sulfur atom or an oxygen atom.)
[0580] In the second acceptor material, a1 and a2 in formulas (P16) and (P17) are preferably ring structures represented by formula (P11A).
[0581] The compound represented by the above formula (P16) is preferably represented by the following formula (P161). The compound represented by formula (P17) is preferably represented by the following formula (P171).
[0582] [ka]
[0583] (In the above formulas (P161) and (P171), X 13 , X 14 , X 15 and X 16 These are, independently, equivalent to Xa and Xb in the above formula (P13), R 141 , R 142 , R 143 and R144 Each of these independently corresponds to R in equation (P13) above. 17 and R 18 It is synonymous with, X 19 (This is either a sulfur atom or an oxygen atom.)
[0584] In the second acceptor material, R in formulas (P16), (P161), (P17), and (P171) 141 , R 142 , R 143 and R 144 At least one of them is Fluorine atom, Fluoroalkyl groups, Fluoroalkoxy group, Cyano group, A ring-forming aromatic hydrocarbon group having 6 to 30 carbon atoms, having at least one substituent selected from the group consisting of a fluorine atom, a fluoroalkyl group, a fluoroalkoxy group, and a cyano group, or It is preferable that the heterocyclic group has 5 to 30 ring-forming atoms and has at least one substituent selected from the group consisting of a fluorine atom, a fluoroalkyl group, a fluoroalkoxy group, and a cyano group.
[0585] In the second acceptor material, it is preferable that two or three structures represented by the formula (P13) are identical to each other.
[0586] The second ring structure represented by formula (P12) is preferably a ring structure represented by the following formula (P121) or formula (P122).
[0587] [ka]
[0588] (In the above formula (P121), X1 and X4 are each independently a nitrogen atom or R 121 It is a carbon atom that bonds with, In the above formula (P121), R 121 Furthermore, R in the above formula (P122)122 , R 123 , R 124 and R 125 Each of these independently corresponds to R in equation (P12) above. 15 It is synonymous with multiple R 121 They are either identical or different from one another. In formulas (P121) and (P122), * independently indicates the bonding position with other atoms in the molecule of the second acceptor material.
[0589] The second acceptor material is also preferably a compound represented by the following formula (P121A).
[0590] [ka]
[0591] (In the above formula (P121A), Ar2 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. X1 and X4 are each independently nitrogen atoms or R 121 It is a carbon atom that bonds with R 121 Each of these independently corresponds to R in equation (P12) above. 15 It is synonymous with multiple R 121 They are either identical or different to one another.
[0592] The second acceptor material is also preferably a compound represented by the following formula (P121B).
[0593] [ka]
[0594] (In the above formula (P121B), X1 and X4 are each independently nitrogen atoms or R 121A carbon atom bonded to, where multiple X1s are either identical or different from each other, and multiple X4s are either identical or different from each other. R 121 Each of these independently corresponds to R in equation (P12) above. 15 It is synonymous with multiple R 121 They are either identical or different to one another.
[0595] The second ring structure represented by formula (P12) may also preferably be included in the second acceptor material as a group represented by the following formula (P122B).
[0596] [ka]
[0597] (In the above formula (P122B), R 122 ~R 125 Each of these independently corresponds to R in equation (P12) above. 15 This is synonymous, and in formula (P122B) above, * indicates the bonding position with other atoms in the molecule of the second acceptor material.
[0598] The second acceptor material is also preferably a compound represented by the following formula (P122C).
[0599] [ka]
[0600] (In the above formula (P122C), R 122 ~R 125 Each of these independently corresponds to R in equation (P12) above. 15 This is synonymous with Alp1, which is a substituted or unsubstituted aliphatic ring with 3-6 ring-forming carbon atoms.
[0601] The second acceptor material is also preferably a compound represented by the following formula (P122D).
[0602] [ka]
[0603] (In the above formula (P122D), R 122 ~R 125 Each of these independently corresponds to R in equation (P12) above. 15 It is synonymous with, Multiple R 122 They are either identical or different from one another. Multiple R 123 They are either identical or different from one another. Multiple R 124 They are either identical or different from one another. Multiple R 125 They are either identical or different from one another. Alp1 is a substituted or unsubstituted aliphatic ring with 3 to 6 ring-forming carbon atoms.
[0604] The second acceptor material is also preferably a compound represented by the following formula (P122E).
[0605] [ka]
[0606] (In the above formula (P122E), nx is 1, 2, 3, or 4. The structures represented by =X1, =X2, and =X3 are each independently represented by the following formulas (PE1), (PE2), (PE3), or (PE4).
[0607] [ka]
[0608] (In formulas (PE1), (PE2), (PE3), and (PE4) above, =X4 and =X5 are independently selected from oxo (=O) and dicyanomethylidene (=C(CN)2), R 1225These are substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms. R 1226 These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 1221 ~R 1224 Each of them operates independently. hydrogen atom, halogen atom, Cyano group, 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 It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.
[0609] When nx is 1, the above equation (P122E) is expressed as the following equation (P1221E); when nx is 2, the above equation (P122E) is expressed as the following equation (P1222E); when nx is 3, the above equation (P122E) is expressed as the following equation (P1223E); and when nx is 4, the above equation (P122E) is expressed as the following equation (P1224E).
[0610] [ka]
[0611] (In the above formulas (P1221E), (P1222E), (P1223E), and (P1224E), The structures represented by =X1, =X2, and =X3 are each independently represented by the above formulas (PE1), (PE2), (PE3), or (PE4), Multiple structures represented by =X2 are either identical or different from one another.
[0612] It is preferable that =X1, =X2, and =X3 have the structure represented by the above formula (PE3).
[0613] The structure represented by formula (PE3) is preferably the structure represented by formula (P11k).
[0614] In the above formula (P11k), R 111 ~R 115 Each of these is preferably an independent halogen atom or a cyano group. In the above formula (P11k), R 111 ~R 115 Four of them are halogen atoms, and R 111 ~R 115 Preferably, one of them is a cyano group. In the above formula (P11k), R 111 , R 112 ,R 114 and R 115 However, it is a halogen atom, R 113 It is preferable that the group is a cyano group. R in the above formula (P11k) 111 ~R 115 In particular, the halogen atom is preferably a fluorine atom.
[0615] In the acceptor materials (first acceptor material and second acceptor material), the substituents in the phrase "substituted or unsubstituted" are, independently, an unsubstituted C1-C25 alkyl group, an unsubstituted C2-C25 alkenyl group, an unsubstituted C2-C25 alkynyl group, an unsubstituted ring-forming C3-C25 cycloalkyl group, 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 unsubstituted aralkyl group with 7 to 50 carbon atoms, -C(=O)R 908 The base represented by -COOR 909 The base represented by -P(=O)(R 931 )(R 932 The group represented by -Ge(R 933 )(R 934 )(R 935 A base represented by -B(R 936 )(R 937 The group represented by -S(=O)2R 938It is also preferable that the group represented by is a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 25 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring-forming atoms. Here, R 901 ~R 909 , and R 931 ~R 938 Preferably, each of these is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring-forming atoms.
[0616] In the acceptor materials (first acceptor material and second acceptor material), the substituents in the case of "substituted or unsubstituted" are preferably, independently, a halogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring-forming atoms.
[0617] In the acceptor materials (first acceptor material and second acceptor material), the substituents in the phrase "substituted or unsubstituted" are preferably, independently, an unsubstituted C1-C6 alkyl group, an unsubstituted ring-forming C6-C13 aryl group, or an unsubstituted ring-forming C5-C13 heterocyclic group.
[0618] The acceptor materials (first acceptor material and second acceptor material) preferably have at least one cyano group.
[0619] In the organic EL element according to this embodiment, the hole injection layer contains a hole transport band material, the acceptor material and the hole transport band material are different from each other, and the content of the acceptor material in the hole injection layer may be less than 50% by mass.
[0620] In the organic EL element according to this embodiment, the content of the acceptor material in the hole injection layer may be 10% by mass or less, or 5% by mass or less.
[0621] In the organic EL element according to this embodiment, the content of the acceptor material in the hole injection layer may be 0.5% by mass or more, 1% by mass or more, 2% by mass or more, or 3% by mass or more.
[0622] In the organic EL element according to this embodiment, if the hole injection layer contains an acceptor material and a hole transport band material, the content of the hole transport band material in the hole injection layer may be independently 40% by mass or more, 45% by mass or more, 50% by mass or more, 90% by mass or more, or 95% by mass or more. The content of the hole transport band material in the hole injection layer may be 99.5% by mass or less, 99% by mass or less, or 97% by mass or less. The total content of the acceptor material and the hole transport band material in the hole injection layer is 100% by mass or less.
[0623] In this specification, an ester group is at least one group selected from the group consisting of alkyl ester groups and aryl ester groups.
[0624] In this specification, alkyl ester groups are, for example, -C(=O)OR E It is represented as R E For example, this is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably 1 to 10 carbon atoms).
[0625] In this specification, the aryl ester group is, for example, -C(=O)OR Ar It is represented as R Ar These are, for example, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms forming a ring.
[0626] In this specification, the siloxanyl group is a silicon compound group via an ether bond, such as a trimethylsiloxanyl group.
[0627] In this specification, the carbamoyl group is represented by -CONH2. Substituted carbamoyl groups in this specification are, for example, -CONH-Ar C , or -CONH-R C It is represented as Ar CThis is, for example, at least one group selected from the group consisting of substituted or unsubstituted aryl groups with 6 to 50 (preferably 6 to 10) ring-forming carbon atoms and heterocyclic groups with 5 to 50 (preferably 5 to 14) ring-forming atoms. C This may be a group formed by bonding a substituted or unsubstituted aryl group with 6 to 50 ring-forming carbon atoms to a substituted or unsubstituted heterocyclic group with 5 to 50 ring-forming atoms. C For example, this is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably 1 to 6 carbon atoms).
[0628] In the second acceptor material, it is also preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.
[0629] (Specific examples of second acceptor materials) Specific examples of the second acceptor material include the following compounds. However, the present invention is not limited to these specific examples of the second acceptor material.
[0630] [ka]
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[0648] <Second host material> In one embodiment of the organic EL element according to this embodiment, the second host material is at least one selected from the group consisting of the compounds shown in (1) to (4) below. (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives (3) Condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives (4) Aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives
[0649] Specifically, examples of metal complexes include tris(8-quinolinolato)aluminum(III) (abbreviated as Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviated as BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviated as BAlq), bis(8-quinolinolato)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviated as ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviated as ZnBTZ). Examples of heterocyclic compounds include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviated as TAZ), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviated as TPBI), vasophenanthroline (abbreviated as BPhen), and vasocuproin (abbreviated as BCP).
[0650] Examples of condensed aromatic compounds include 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviated as CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviated as DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviated as DPPA), 9,10-di(2-naphthyl)anthracene (abbreviated as DNA), and 2-tert-butyl-9,10-di(2-naphthyl)anthracene Examples include t-BuDNA (abbreviated as t-BuDNA), 9,9'-biantryl (abbreviated as BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviated as DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviated as DPNS2), 3,3',3''-(benzene-1,3,5-triyl)tripylene (abbreviated as TPB3), 9,10-diphenylanthracene (abbreviated as DPAnth), and 6,12-dimethoxy-5,11-diphenylchrysene.
[0651] Aromatic amine compounds include N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviated as CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviated as DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviated as PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviated as PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCAPA), NPB (or α-NPD), TPD, DFLDPBi, BSPB, and others.
[0652] In one embodiment of the organic EL element according to this embodiment, the second host material may be, for example, at least one selected from the group consisting of the compounds shown in (1) to (4) above. In one embodiment of the organic EL element according to this embodiment, the second host material contains in its molecule at least one of the structures described in condition (i) and condition (ii).
[0653] Condition (i) The biphenyl structure has a first benzene ring and a second benzene ring linked by a single bond, and the first benzene ring and the second benzene ring in the biphenyl structure are further linked by crosslinking at least one portion other than the single bond.
[0654] Condition (ii) Having a first linkage structure comprising a benzene ring and a naphthalene ring linked by a single bond, wherein the benzene ring and the naphthalene ring in the first linkage structure are independently further fused or unfused with a single ring or a fused ring, and the benzene ring and the naphthalene ring in the first linkage structure are further linked by crosslinking at least one portion other than the single bond.
[0655] In one embodiment of the organic EL element according to this embodiment, the second host material contains the structure of condition (i) in its molecule.
[0656] In one embodiment of the organic EL element according to this embodiment, the first benzene ring and the second benzene ring in the biphenyl structure under condition (i) are further connected by the crosslinking under condition (i) at one portion other than the single bond. Because the second host material has a biphenyl structure containing such crosslinking, it is expected that chromaticity degradation will be suppressed when the second host material is used in the light-emitting layer of an organic EL element.
[0657] In one embodiment of the organic EL element according to this embodiment, the first benzene ring and the second benzene ring in the biphenyl structure of condition (i) are further connected by the crosslinking of condition (i) at two portions other than the single bond.
[0658] In one embodiment of the organic EL element according to this embodiment, the crosslinking in condition (i) includes a double bond.
[0659] In one embodiment of the organic EL element according to this embodiment, the crosslinking in condition (i) does not include a double bond.
[0660] In one embodiment of the organic EL element according to this embodiment, the second host material has the structure of condition (i) in its molecule, and the first benzene ring and the second benzene ring in the biphenyl structure are further linked by the crosslinking of condition (i) at two portions other than the single bond, and the crosslinking of condition (i) does not contain a double bond. Because the second host material has a biphenyl structure including such crosslinking, when the second host material is used in the light-emitting layer of the organic EL element, it is expected that the deterioration of chromaticity will be suppressed.
[0661] For example, if the first benzene ring and the second benzene ring in the biphenyl structure represented by the following formula (BP1) are further linked by crosslinking at at least one part other than the single bond, the biphenyl structure becomes a linked structure (condensed ring) such as those represented by the following formulas (BP11) to (BP15).
[0662] [ka]
[0663] The above formula (BP11) is a structure in which the parts other than the single bond are connected by a bridge that does not contain a double bond. The above formula (BP12) is a structure in which the parts other than the single bond are connected by a bridge containing a double bond. The above formula (BP13) is a structure in which the two parts other than the single bond are connected by bridges that do not contain double bonds. The above formula (BP14) is a structure in which one of the two parts other than the single bond is connected by a bridge that does not contain a double bond, and the other of the two parts other than the single bond is connected by a bridge that contains a double bond. The above formula (BP15) is a structure in which the two parts other than the single bond are connected by bridges containing double bonds.
[0664] In one embodiment of the organic EL element according to this embodiment, the second host material contains the structure of condition (ii) in its molecule.
[0665] Because the second host material has a linked structure including such cross-linking, it is expected that chromaticity degradation will be suppressed when the second host material is used in the light-emitting layer of an organic EL element. In this case, the second host material only needs to have a first linkage structure (sometimes referred to as a benzene-naphthalene linkage structure) as its minimum unit in the molecule, which includes a benzene ring and a naphthalene ring linked by a single bond, as represented by the following formula (X1) or formula (X2). A single ring or fused ring may be further fused to the benzene ring, or a single ring or fused ring may be further fused to the naphthalene ring. For example, even if the second host material has a second linkage structure (sometimes referred to as a naphthalene-naphthalene linkage structure) in the molecule, which includes a naphthalene ring and a naphthalene ring linked by a single bond, as represented by the following formula (X3), formula (X4), or formula (X5), one of the naphthalene rings contains a benzene ring, and therefore contains a benzene-naphthalene linkage structure.
[0666] [ka]
[0667] In one embodiment of the organic EL element according to this embodiment, the crosslinking in condition (ii) includes a double bond. That is, it is also preferable that the benzene ring and the naphthalene ring have a structure in which they are further connected by a crosslinking structure that includes a double bond in the portion other than the single bond.
[0668] If the benzene ring and naphthalene ring in the first linkage structure (benzene-naphthalene linkage structure) are further linked by crosslinking at at least one portion other than the single bond, for example, in the case of formula (X1), a linkage structure (condensed ring) represented by the following formula (X11) is formed, and in the case of formula (X3), a linkage structure (condensed ring) represented by the following formula (X31) is formed. When the benzene ring and naphthalene ring in the benzene-naphthalene linkage structure are further linked by crosslinking including double bonds in parts other than the single bond, for example, in the case of formula (X1), a linkage structure (condensed ring) represented by formula (X12) is formed; in the case of formula (X2), a linkage structure (condensed ring) represented by formula (X21), formula (X22), or formula (X23) is formed; in the case of formula (X4), a linkage structure (condensed ring) represented by formula (X41) is formed; and in the case of formula (X5), a linkage structure (condensed ring) represented by formula (X51) is formed. If the benzene ring and naphthalene ring in the benzene-naphthalene linkage structure are further linked by a bridge containing a heteroatom (e.g., an oxygen atom) at at least one portion other than the single bond, then, for example, in the case of formula (X1), a linkage structure (fused ring) represented by the following formula (X13) is formed.
[0669] [ka]
[0670] In one embodiment of the organic EL element according to this embodiment, the second host material is preferably a compound selected from the group consisting of a compound represented by the following formula (H11), a compound represented by the formula (H12), a compound represented by the formula (H13), a compound represented by the formula (H14), a compound represented by the formula (H15), and a compound represented by the formula (H16).
[0671] (Compound represented by formula (H11))
[0672] [ka]
[0673] (In the above formula (H11), R 101 ~R 110 , and 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 ) 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, 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. However, R 101 ~R 110 One of them is L 101 This indicates the bonding position with R 111 ~R 120 One of them is L 101 It shows the bonding position with, L 101 teeth, single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 24 carbon atoms, or A divalent heterocyclic group having 5 to 24 substituted or unsubstituted ring-forming atoms, mx is 0, 1, 2, 3, 4, or 5. L 101 If there are 2 or more, then 2 or more L 101 They are either identical or different to one another.
[0674] (The compound represented by formula (H12))
[0675] [ka]
[0676] (In the above formula (H12), Xa consists of an oxygen atom, a sulfur atom, and C(R) 1201 )(R 1202 ), or Si(R 1203 )(R 1204 ) and R 1201 ~R 1204 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 121 ~R 130 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 121 ~R 130 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 above formula (H121), However, R 121 ~R 130 At least one of them is a group represented by the formula (H121), If there are multiple groups represented by the formula (H121), the multiple groups represented by the formula (H121) may be identical or different from each other. L 12 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, ma is 0, 1, 2, or 3. L 12 If there are 2 or more, then 2 or more L 12 They are either identical or different from each other. Ar 12 This 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. Ar 12 If there are 2 or more Ar 12 They are either identical or different from each other. In the above formula (H121), * indicates the bond position.
[0677] (Compound represented by formula (H13))
[0678] [ka]
[0679] (In the above formula (H13), R 131 ~R 134 and R 139 ~R 140 Of these, one or more pairs consisting of two or more adjacent items, They combine with each other to form a substituted or unsubstituted monoring, or They do not connect with each other, R 135 ~R 138 Of these, one or more pairs consisting of two or more adjacent items, They combine with each other to form a substituted or unsubstituted monoring, or They do not connect with each other, Ar 131 Ar 132 , and R that does not form a monoring with or without substitution 131 ~R 140 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 ) 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, Cyano group, 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 above formula (H131), However, R 131 ~R 140 Ar 131 and Ar 132 At least one of them is a group represented by the formula (H131), If there are multiple groups represented by the above formula (H131), the multiple groups represented by the above formula (H131) may be identical or different from each other. L 13 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, Ar 13 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. mb is 0, 1, 2, 3, 4, or 5. L 13 If there are 2 or more, then 2 or more L 13 They are either identical or different from each other. Ar 13 If there are 2 or more Ar 13 They are either identical or different from each other. The asterisk (*) in formula (H131) indicates the bonding position with the benz[a]anthracene ring in formula (H13).
[0680] (Compound represented by formula (H14))
[0681] [ka]
[0682] (In the above formula (H14), R 1A and R 1B Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 15 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 17 carbon atoms, or These are heterocyclic groups with 5 to 17 substituted or unsubstituted ring-forming atoms. However, R 1A and R 1B At least one of ...
Claims
1. Anode and, Cathode and, One or more light-emitting bands are arranged between the anode and the cathode, It has one or more charge generation and transport bands arranged between the anode and the cathode, Each of the aforementioned one or more light-emitting bands independently includes one or more light-emitting layers. Of the one or more light emission bands, at least one includes the first light emission layer. The first light-emitting layer contains a compound represented by the following formula (2) as a first host material, and the first host material has at least one deuterium atom. Each of the one or more charge generation and transport bands independently includes at least one band selected from the group consisting of charge generation bands and charge transport bands. Of the one or more charge generation and transport bands, at least one includes the first organic layer. The first organic layer contains a compound represented by the following formula (AC1): Organic electroluminescent element. 【Chemistry 1】 (In the above formula (AC1), R 11 , R 12 , R 13 and R 14 Each of these is independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, or a nitro group. X 11 is a nitrogen atom or C(Q 11 ) and X 12 is a nitrogen atom or C(Q 12 ) and X 13 is a nitrogen atom or C(Q 13 ) and X 14 is a nitrogen atom or C(Q 14 ) and X 15 is a nitrogen atom or C(Q 15 ) and X 16 is a nitrogen atom or C(Q 16 ) and Q 11 Q 12 Q 13 Q 14 Q 15 , and Q 16 These are, independently, a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, or a nitro group. (In the above 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, 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 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 compound represented by 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.)
2. In the organic electroluminescent element according to claim 1, Ar in formula (2) 201 and Ar 202 At least one of them is a group represented by the following formula (HY1), Organic electroluminescent element. 【Chemistry 2】 (In the above formula (HY1), R Y1 ~R Y8 and R Y11 ~R Y14 Each of them operates independently. hydrogen atom, halogen atom, Cyano group, Nitro group, 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 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, ny is either 0 or 1. however, When ny is 0, R Y1 ~R Y8 One of the options is a single join that connects to *ey, When ny is 1, one condition is satisfied which is selected from the group consisting of (a1) to (a3) below, and R Y5 ~R Y8 , R Y11 ~R Y14 , as well as R which is not a single bond attached to *cy and *dy Y1 ~R Y4 One of the group selected from the group consisting of is a single bond that joins *ey. (a1) R Y1 and R Y2 One of them is a single bond that connects to *cy, and R Y1 and R Y2 The other side is a single bond that connects to *dy. (a2) R Y2 and R Y3 one of them is a single bond that binds to *cy, and Y2 and R Y3 the other is a single bond that binds to *dy. (a3) R Y3 and R Y4 one of which is a single bond connecting to *cy, and Y3 and R Y4 the other is a single bond connecting to *dy. Z 2 is an oxygen atom or a sulfur atom, *fy is L in the first host material. 201 or L 202 (This indicates the bonding position.)
3. In the organic electroluminescent element according to claim 1 or claim 2, Ar in formula (2) 201 and Ar 202 At least one of them is a group selected from the group consisting of groups represented by the following formulas (HY11), (HY12), and (HY13): Organic electroluminescent element. 【Transformation 3】 【Chemistry 4】 【Transformation 5】 (In the above formulas (HY11), (HY12), and (HY13), R Y1 ~R Y8 , R Y11 ~R Y14 , and Z 2 These are, respectively, R in the above formula (HY1). Y1 ~R Y8 , R Y11 ~R Y14 , and Z 2 It is synonymous with, However, R Y1 ~R Y8 and R Y11 ~R Y14 Of these, one is a single bond that connects to *ey, *fy is L in the first host material. 201 or L 202 (This indicates the bonding position.)
4. In the organic electroluminescent element according to claim 3, Ar 201 or Ar 202 teeth, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms. Organic electroluminescent element.
5. In the organic electroluminescent element according to claim 3 or claim 4, Ar 201 or Ar 202 teeth, Substituted or unsubstituted phenyl groups, Substituted or unsubstituted biphenyl groups, Substituted or unsubstituted terphenyl groups, Substituted or unsubstituted naphthyl groups, Substituted or unsubstituted phenanthryl groups, Substituted or unsubstituted benzophenanthryl groups, A substituted or unsubstituted benzoantryl group, A substituted or unsubstituted triphenylenyl group, Organic electroluminescent element.
6. In the organic electroluminescent element according to claim 1, Ar 201 and Ar 202 Each of them operates independently. A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms. Organic electroluminescent element.
7. In the organic electroluminescent element according to claim 6, Ar 201 and Ar 202 Each of them operates independently. Substituted or unsubstituted phenyl groups, Substituted or unsubstituted biphenyl groups, Substituted or unsubstituted terphenyl groups, Substituted or unsubstituted naphthyl groups, Substituted or unsubstituted phenanthryl groups, Substituted or unsubstituted benzophenanthryl groups, A substituted or unsubstituted benzoantryl group, A substituted or unsubstituted triphenylenyl group, Organic electroluminescent element.
8. In an organic electroluminescent element according to any one of claims 1 to 7, L 201 and L 202 Each of them operates independently. Single bond, or A substituted or unsubstituted ring-forming arylene group having 6 to 18 carbon atoms. Organic electroluminescent element.
9. In an organic electroluminescent element according to any one of claims 1 to 8, -L 201 -Ar 201 The group represented by -L 202 -Ar 202 At least one of the groups represented by is independently a group represented by any of the following formulas (2-11a) to (2-41a): Organic electroluminescent element. 【Transformation 6】 【Transformation 7】 【Transformation 8】 (In formulas (2-11a) to (2-41a) above, Ra to Rg are each independently a hydrogen atom, an unsubstituted C1-C50 alkyl group, an unsubstituted C2-C50 alkenyl group, an unsubstituted C2-C50 alkynyl group, an unsubstituted ring-forming C3-C50 cycloalkyl group, and -Si(R 901 ) (Caution 902 ) (Caution 903 A group represented by ) -O-(R 904 A group represented by -S-(R 905 A group represented by ), -N(R 906 ) (Caution 907 A group represented by ), an unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 The base represented by -COOR 802 A group selected from the group consisting of a group represented by , a halogen atom, a cyano group, a nitro group, and an unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each of these is R in the first host material. 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 (This is synonymous with the above, and * indicates the binding position.)
10. In the organic electroluminescent element according to claim 9, At least one of Ra to Rg is a deuterium atom. Organic electroluminescent element.
11. In an organic electroluminescent element according to any one of claims 1 to 10, 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 ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by Cyano group, 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. Organic electroluminescent element.
12. In an organic electroluminescent element according to any one of claims 1 to 11, R 201 ~R 208 At least one of them is a deuterium atom. Organic electroluminescent element.
13. In an organic electroluminescent element according to any one of claims 1 to 12, The one or more charge generation transport bands have a first charge generation transport band that includes the first overnight period. The first charge generation transport band is located between the light emission band closest to the anode and the anode, among the one or more light emission bands. Organic electroluminescent element.
14. In an organic electroluminescent element according to any one of claims 1 to 13, The one or more light-emitting layers include one or more light-emitting layers containing a light-emitting compound having fluorescent properties. Organic electroluminescent element.
15. In an organic electroluminescent element according to any one of claims 1 to 14, The first light-emitting layer contains a first light-emitting compound that exhibits light emission with a maximum peak wavelength of 430 nm or more and 480 nm or less. Organic electroluminescent element.
16. In an organic electroluminescent element according to any one of claims 1 to 15, The aforementioned one or more emission bands are two or more emission bands. The two or more emission bands include at least a first emission band and a second emission band. The one or more charge generation transport bands have a second charge generation transport band that includes the first overnight period. The second charge generation transport band is positioned between the first emission band and the second emission band. The first light-emitting band, the first organic layer, and the second light-emitting band are arranged in this order from the anode side. Organic electroluminescent element.
17. In an organic electroluminescent element according to any one of claims 1 to 16, In the compound represented by the above formula (AC1), R 11 , R 12 , R 13 and R 14 These are, independently, a cyano group or a nitro group. Organic electroluminescent element.
18. In an organic electroluminescent element according to any one of claims 1 to 17, The compound represented by the above formula (AC1) is the compound represented by the following formula (AC2). Organic electroluminescent element. 【Chemistry 9】 (In the above formula (AC2), X 11 , X 12 , X 13 , X 14 , X 15 , and X 16 These are, respectively, X in the above formula (AC1). 11 , X 12 , X 13 , X 14 , X 15 , and X 16 (This is synonymous with...)
19. In an organic electroluminescent element according to any one of claims 1 to 17, The compound represented by the above formula (AC1) is the compound represented by the following formula (AC3). Organic electroluminescent element. 【Chemistry 10】 (In the above formula (AC3), R 11 , R 12 , R 13 , R 14 Q 11 Q 12 Q 13 Q 14 Q 15 , and Q 16 These are, respectively, R in the above formula (AC1). 11 , R 12 , R 13 , R 14 Q 11 Q 12 Q 13 Q 14 Q 15 , and Q 16 (This is synonymous with...)
20. In the organic electroluminescent element according to claim 19, The compound represented by the above formula (AC1) is the compound represented by the following formula (AC4). Organic electroluminescent element. 【Chemistry 11】 (In the above formula (AC4), Q 11 Q 12 Q 13 Q 14 Q 15 , and Q 16 These are, respectively, Q in the above formula (AC1). 11 Q 12 Q 13 Q 14 Q 15 , and Q 16 (This is synonymous with...)
21. In an organic electroluminescent element according to any one of claims 1 to 20, In the compound represented by the above formula (AC1), Q 11 Q 12 Q 13 Q 14 Q 15 , and Q 16 These are, independently, a hydrogen atom, a fluorine atom, or a cyano group. Organic electroluminescent element.
22. In an organic electroluminescent element according to any one of claims 1 to 21, In the compound represented by the above formula (AC1), Q 11 Q 12 Q 13 Q 14 Q 15 , and Q 16 These are, independently, a fluorine atom or a cyano group. Organic electroluminescent element.
23. In an organic electroluminescent element according to any one of claims 1 to 22, In the compound represented by the above formula (AC1), Q 11 Q 12 Q 13 Q 14 Q 15 , and Q 16 This is a fluorine atom, Organic electroluminescent element.
24. An electronic device equipped with an organic electroluminescent element according to any one of claims 1 to 23.