Triazine compound, material for organic electroluminescent elements, electron transport material for organic electroluminescent elements, and organic electroluminescent element

Abstract

A triazine compound, a material for organic electroluminescent elements, an electron transport material for organic electroluminescent elements, and an organic electroluminescent element. The purpose of the present invention is to provide a triazine compound which contributes to the production of an organic electroluminescent element having excellent driving voltage and durability. A triazine compound represented by formula (1). In formula (1), A and B each represents an aryl group having 6-20 carbon atoms. L represents a phenyl group or a naphthyl group. And n is 0 or 1. And C represents any one group selected from the group consisting of X, Y, and Z. And Ar1 and Ar2 each represents an aromatic hydrocarbon group or a pyridyl group.

Description

[0001] This application is a divisional application of the application filed on October 1, 2021, with application number 202180068136.4 and invention title "Triazine Compound, Material for Organic Electroluminescent Device, Electron Transport Material for Organic Electroluminescent Device and Organic Electroluminescent Device". Technical Field

[0002] This invention relates to triazine compounds, materials for organic electroluminescent devices, electron transport materials for organic electroluminescent devices, and organic electroluminescent devices. Background Technology

[0003] Organic electroluminescent elements are not only used in small displays, but also in large televisions, lighting, and other applications, and their development is actively underway.

[0004] Existing technical documents

[0005] Patent documents

[0006] Patent Document 1: Japanese Patent Publication No. 2019-512499

[0007] Patent Document 2: Japanese Patent Application Publication No. 2018-95562

[0008] Patent Document 3: International Publication No. 2015 / 111848 Summary of the Invention

[0009] The problem the invention aims to solve

[0010] In recent years, the market has increasingly demanded organic electroluminescent elements, seeking materials that excel in current efficiency, driving voltage, and long lifespan.

[0011] Here, Patent Document 1 discloses triazine compounds with different substituents at positions 2, 4, and 6; Patent Document 2 discloses triazine compounds having a 1,2-phenylene site; and Patent Document 3 discloses azazine compounds with a phenyl substituted position 2.

[0012] However, the organic electroluminescent devices obtained by using the compounds disclosed in Patent Documents 1 to 3 as electron transport layers are not sufficient in terms of driving voltage and driving lifetime characteristics, and further improvements are sought.

[0013] One aspect of the present invention relates to providing triazine compounds that facilitate the fabrication of organic electroluminescent elements with low driving voltage and excellent durability; materials for organic electroluminescent elements; and electron transport materials for organic electroluminescent elements.

[0014] In addition, other aspects of the present invention are directed to providing organic electroluminescent elements with low driving voltage and excellent durability.

[0015] Solution for solving the problem

[0016] According to one aspect of the present invention, a triazine compound of formula (1) is provided.

[0017] The triazine compound shown in formula (1).

[0018]

[0019] In equation (1),

[0020] A and B represent aryl groups with 6 to 20 carbon atoms.

[0021] L represents phenyl or naphthyl. n is 0 or 1.

[0022] C represents any one of the following groups: X, Y, and Z.

[0023]

[0024] Ar 1 Ar 2 It indicates an aromatic hydrocarbon group or a pyridyl group.

[0025] According to one aspect of the present invention, the triazine compound represented by formula (1) includes the triazine compounds represented by formulas X (1), Y (1) and Z (1) below.

[0026] A, B, L, n, Ar 1 Ar 2 The triazine compounds represented by formulas X(1), Y(1), and Z(1) are specified respectively.

[0027] According to one aspect of the present invention, a triazine compound of formula X(1) is provided.

[0028]

[0029] In the case of equation X(1),

[0030] A represents any group selected from formulas X(A-1) to X(A-9):

[0031]

[0032] B represents any group selected from formulas X(B-1) to X(B-15):

[0033]

[0034] Ar 1 express:

[0035] Choose one or more aryl groups with 6 to 30 carbon atoms selected from the group consisting of alkyl groups with 1 to 12 carbon atoms, cycloalkyl groups with 3 to 20 carbon atoms, cyano, diarylboroyl, and phosphine oxide, or

[0036] Pyridyl group optionally substituted with methyl or phenyl;

[0037] Ar 2 express:

[0038] Choose one or more aryl groups with 6 to 30 carbon atoms selected from the group consisting of alkyl groups with 1 to 12 carbon atoms, cycloalkyl groups with 3 to 20 carbon atoms, cyano, diarylboroyl, and phosphine oxide, or

[0039] Pyridyl groups may be optionally substituted with methyl or phenyl groups.

[0040] According to another aspect of the invention, a triazine compound of formula Y(1) is provided:

[0041]

[0042] In the case of equation Y(1),

[0043] A represents an aryl group with 6 to 20 carbon atoms;

[0044] B indicates:

[0045] Choose one or more aryl groups with 6 to 20 carbon atoms selected from the group consisting of alkyl groups having 1 to 12 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cyano, diarylboroyl, and phosphine oxide, or

[0046] Heteroaryl groups having 4 to 30 carbon atoms and containing oxygen or sulfur atoms;

[0047] Ar 1 ~Ar 2 Each is expressed independently:

[0048] Choose one or more aryl groups with 6 to 26 carbon atoms selected from the group consisting of alkyl groups with 1 to 12 carbon atoms, cycloalkyl groups with 3 to 20 carbon atoms, cyano groups, diarylboro groups, and phosphine oxide groups, or

[0049] Pyridyl group optionally substituted with methyl or phenyl;

[0050] n represents an integer from 0 to 1;

[0051] L represents any group selected from formulas Y(2-1) to Y(2-5).

[0052]

[0053] According to another aspect of the invention, a triazine compound of formula Z(1) is provided:

[0054]

[0055] In the case of equation Z(1),

[0056] A represents a phenyl, biphenyl, or naphthyl group substituted with one or more substituents from the group consisting of the selected free fluorine atom, methyl group, and cyano group;

[0057] B represents a phenyl, biphenyl, or naphthyl group, which is substituted by one or more substituents from the group consisting of the selected free fluorine atom, methyl group, and cyano group;

[0058] Ar 1 The group consisting of one or more substituents, phenyl or naphthyl, is selected to be substituted by one or more substituents from the group consisting of free fluorine atom, methyl and cyano group;

[0059] Ar 2 It indicates a phenyl or naphthyl group that is substituted with one or more substituents from the group consisting of a free fluorine atom, a methyl group, and a cyano group.

[0060] According to other aspects of the present invention, materials for organic electroluminescent elements comprising the above-described triazine compounds are provided.

[0061] According to other aspects of the present invention, an electron transport material for an organic electroluminescent element comprising the above-described triazine compound is provided.

[0062] According to other aspects of the present invention, an organic electroluminescent element comprising the above-described triazine compound is provided.

[0063] The effects of the invention

[0064] According to one aspect of the present invention, triazine compounds that facilitate the fabrication of organic electroluminescent elements with low driving voltage and excellent durability can be provided; materials for organic electroluminescent elements and electron transport materials for organic electroluminescent elements.

[0065] According to other aspects of the present invention, organic electroluminescent elements with low driving voltage and excellent durability can be provided. Attached Figure Description

[0066] Figure 1 This is a schematic cross-sectional view illustrating an example of a stacked configuration of an organic electroluminescent element comprising a triazine compound as described in one aspect of the present invention.

[0067] Figure 2 This is a schematic cross-sectional view showing an example of a stacked configuration of an organic electroluminescent element comprising a triazine compound as described in one aspect of the present invention (element example-1, etc.).

[0068] Explanation of reference numerals in the attached figures

[0069] 1.101 substrate

[0070] 2. 102 anode

[0071] 3. 103 Hole Injection Layer

[0072] 4. 104 charge generation layer

[0073] 5. 105 Hole Transport Layer

[0074] 6. 106 light-emitting layers

[0075] 7. Electron transport layer 107

[0076] 8. 108 cathode

[0077] 51, 1051 First Hole Transport Layer

[0078] 52, 1052 Second Hole Transport Layer

[0079] 71, 1071 First Electron Transport Layer

[0080] 72, 1072 Second Electron Transport Layer

[0081] 100 Organic Electroluminescent Element Detailed Implementation

[0082] The triazine compound described below, according to one embodiment of the present invention, will be described in detail below.

[0083] <Triazine compounds>

[0084] According to one aspect of the present invention, a triazine compound of formula (1) is provided.

[0085] The triazine compound shown in formula (1).

[0086]

[0087] In equation (1),

[0088] A and B represent aryl groups with 6 to 20 carbon atoms.

[0089] L represents phenyl or naphthyl. n is 0 or 1.

[0090] C represents any one of the following groups: X, Y, and Z.

[0091]

[0092] Ar 1 Ar 2 It indicates an aromatic hydrocarbon group or a pyridyl group.

[0093] The triazine compound represented by formula (1) includes the triazine compounds shown in formulas X (1), Y (1) and Z (1) below. Hereinafter, the embodiments shown in formulas X (1), Y (1) and Z (1) will be described.

[0094] <Triazine compound X(1)>

[0095] The triazine compound described in one aspect of the present invention is represented by formula X(1).

[0096]

[0097] In the case of equation X(1),

[0098] A represents any group selected from formulas X(A-1) to X(A-9).

[0099]

[0100] B represents any group selected from formulas X(B-1) to X(B-15).

[0101]

[0102] Ar 1 express:

[0103] Choose one or more aryl groups with 6 to 30 carbon atoms selected from the group consisting of alkyl groups with 1 to 12 carbon atoms, cycloalkyl groups with 3 to 20 carbon atoms, cyano, diarylboroyl, and phosphine oxide, or

[0104] Pyridyl group optionally substituted with methyl or phenyl;

[0105] Ar 2 express:

[0106] Choose one or more aryl groups with 6 to 30 carbon atoms selected from the group consisting of alkyl groups with 1 to 12 carbon atoms, cycloalkyl groups with 3 to 20 carbon atoms, cyano, diarylboroyl, and phosphine oxide, or

[0107] Pyridyl groups may be optionally substituted with methyl or phenyl groups.

[0108] [Regarding A, B, and Ar] 1 Ar 2 [Optimal combination]

[0109] In the triazine compound represented by formula X(1), preferred compounds are A, B, and Ar. 1 Ar 2 The combinations, namely the first to the eighth methods, are shown below.

[0110] First method

[0111] A represents any group selected from formulas X(A-1) to X(A-9);

[0112] Ar 1 It refers to an aryl group with 6 to 30 carbon atoms that is selected from the group consisting of alkyl with 1 to 12 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, cyano, diarylboryl and phosphine oxide;

[0113] Ar 2 It means that one or more aryl groups with 6 to 30 carbon atoms are selected from the group consisting of alkyl with 1 to 12 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, cyano, diarylboryl, and phosphine oxide.

[0114] Second method

[0115] B represents any one of the groups selected from formulas X(B-1)~X(B-4), (B-7)~X(B-8), and (B-10)~X(B-11).

[0116] Third method

[0117] A represents any group selected from formulas X(A-1) to X(A-9);

[0118] Ar 1 It refers to an aryl group with 6 to 30 carbon atoms that is selected from the group consisting of alkyl with 1 to 12 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, cyano, diarylboryl and phosphine oxide;

[0119] Ar 2 It means that one or more aryl groups with 6 to 30 carbon atoms are selected from the group consisting of alkyl with 1 to 12 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, cyano, diarylboryl, and phosphine oxide.

[0120] Fourth method

[0121] A represents any group selected from formulas X(A-1) to X(A-4);

[0122] B represents a group selected from formulas X(B-1)~X(B-4), X(B-7)~X(B-8), and X(B-10)~X(B-11);

[0123] Ar 1 It refers to an aryl group with 6 to 30 carbon atoms that is selected from the group consisting of alkyl with 1 to 12 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, cyano, diarylboryl and phosphine oxide;

[0124] Ar 2 It means that one or more aryl groups with 6 to 30 carbon atoms are selected from the group consisting of alkyl with 1 to 12 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, cyano, diarylboryl, and phosphine oxide.

[0125] Fifth method

[0126] Ar 1 The group consisting of alkyl groups having 1 to 12 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cyano, diarylboryl, and phosphine oxide, with one or more substitutions, is phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 2-(1-naphthyl)phenyl, 3-(1-naphthyl)phenyl, 4-(1-naphthyl)phenyl, 2-(2-naphthyl)phenyl, 3-(2-naphthyl)phenyl, 4-(2-naphthyl)phenyl, 4-phenylnaphth-1-yl, 5-phenylnaphth-1-yl, 6-phenylnaphth-2-yl, and 7-phenylnaphth-2-yl.

[0127] Ar 2 The group consisting of alkyl groups having 1 to 12 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cyano, diarylboroyl, and phosphine oxide, with one or more substitutions, is phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 2-(1-naphthyl)phenyl, 3-(1-naphthyl)phenyl, 4-(1-naphthyl)phenyl, 2-(2-naphthyl)phenyl, 3-(2-naphthyl)phenyl, 4-(2-naphthyl)phenyl, 4-phenylnaphth-1-yl, 5-phenylnaphth-1-yl, 6-phenylnaphth-2-yl, and 7-phenylnaphth-2-yl.

[0128] Sixth method

[0129] Ar 1 The group consisting of alkyl groups with 1 to 12 carbon atoms, cycloalkyl groups with 3 to 20 carbon atoms, cyano, diarylboryl, and phosphine oxide, with one or more substitutions, phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl, and 4-biphenyl;

[0130] Ar 2 The group consisting of one or more substituted alkyl, cycloalkyl, cyano, diarylboryl, and phosphine oxide groups with 1 to 12 carbon atoms, phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl, and 4-biphenyl groups are selected.

[0131] ·Seventh Method

[0132] A represents any group selected from formulas X(A-1) to X(A-4);

[0133] B represents any group selected from formulas X(B-1) to X(B-4);

[0134] Ar 1 This indicates phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl, and 4-biphenyl.

[0135] Ar 2 It represents phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl, and 4-biphenyl.

[0136] ·Eighth Method

[0137] A is the group represented by formula X(A-1);

[0138] B is the group represented by formula X(B-1);

[0139] Ar 1 This indicates phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl, and 4-biphenyl.

[0140] Ar 2 It represents phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl, and 4-biphenyl.

[0141] Hereinafter, the triazine compound represented by formula X(1) will sometimes be referred to as triazine compound X(1). The definitions of the substituents in triazine compound X(1) and their preferred specific examples are shown below.

[0142] [Regarding A and B]

[0143] In the case of equation X(1),

[0144] A represents any group selected from formulas X(A-1) to X(A-9).

[0145] B represents any group selected from formulas X(B-1) to X(B-15).

[0146]

[0147]

[0148] A represents any group selected from formulas X(A-1) to X(A-9), preferably any group selected from formulas X(A-1) to X(A-4).

[0149] B represents any group selected from formulas X(B-1) to X(B-15), preferably any group selected from formulas X(B-1) to X(B-4), X(B-7), X(B-8), X(B-10) and X(B-11), and particularly preferably any group selected from formulas X(B-1) to X(B-4).

[0150] Regarding the combination of A and B, when the selectable group of B does not contain a cyano group, such as the combination of the group shown in X(A-1) and the group shown in X(B-1), it is preferable to use the same group.

[0151] [About Ar] 1 Ar 2 ]

[0152] Ar 1 express:

[0153] Choose one or more aryl groups with 6 to 30 carbon atoms selected from the group consisting of alkyl groups with 1 to 12 carbon atoms, cycloalkyl groups with 3 to 20 carbon atoms, cyano, diarylboroyl, and phosphine oxide, or

[0154] Pyridyl group optionally substituted with methyl or phenyl;

[0155] Ar 2 express:

[0156] Choose one or more aryl groups with 6 to 30 carbon atoms selected from the group consisting of alkyl groups with 1 to 12 carbon atoms, cycloalkyl groups with 3 to 20 carbon atoms, cyano, diarylboroyl, and phosphine oxide, or

[0157] Pyridyl groups may be optionally substituted with methyl or phenyl groups.

[0158] Regarding Ar 1 and Ar 2 The aryl group having 6 to 30 carbon atoms in the aryl group, as preferred examples, includes: phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 2-(1-naphthyl)phenyl, 3-(1-naphthyl)phenyl, 4-(1-naphthyl)phenyl, 2-(2-naphthyl)phenyl, 3-(2-naphthyl)phenyl, 4-(2-naphthyl)phenyl, 4-phenylnaphth-1-yl, 5-phenylnaphth-1-yl, 6-phenylnaphth-2-yl, 7-phenylnaphth-2-yl, 2-phenanthyl, 3-phenanthyl, 9-phenanthyl, 9-anthrayl, p-terphenyl, or 2-benzophenanthryl.

[0159] These groups are optionally substituted with alkyl groups having 1 to 12 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cyano, diarylboroyl, and phosphine oxide, more preferably with unsubstituted phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl, or 4-biphenyl, and particularly preferably with phenyl, 2-naphthyl, 2-biphenyl, or 4-biphenyl.

[0160] [Specific examples of triazine compound X(1)]

[0161] Specific examples of particularly preferred compounds among the triazine compounds described in one aspect of the present invention as shown in formula X(1) are listed below X(1-1) to X(1-80), but the triazine compounds described in one aspect of the present invention are not limited to them.

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174] <Triazine compound Y(1)>

[0175] The triazine compound Y(1) described in one aspect of the present invention is represented by the formula Y(1).

[0176]

[0177] In the case of equation Y(1),

[0178] L represents any group selected from formulas Y(2-1) to Y(2-5).

[0179]

[0180] The most preferred option is any group selected from formulas Y(A-1) to Y(A-10).

[0181]

[0182] The most preferred option is any group selected from formulas Y(B-1) to Y(B-28).

[0183]

[0184]

[0185] [About L]

[0186] L represents any group selected from formulas Y(2-1) to Y(2-5).

[0187]

[0188] [Specific examples of triazine compound Y(1)]

[0189] Specific examples of particularly preferred compounds among the triazine compounds described in one aspect of the present invention as shown in formula Y(1) are listed below Y(1-1) to Y(1-179), but the triazine compounds described in one aspect of the present invention are not limited to them.

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207] <Triazine compound Z(1)>

[0208] The triazine compound described in one embodiment of the present invention is represented by formula Z(1).

[0209]

[0210] In the case of equation Z(1),

[0211] A represents a phenyl, biphenyl, or naphthyl group substituted with one or more substituents from the group consisting of the selected free fluorine atom, methyl group, and cyano group;

[0212] B represents a phenyl, biphenyl, or naphthyl group, which is substituted by one or more substituents from the group consisting of the selected free fluorine atom, methyl group, and cyano group;

[0213] Ar 1 The group consisting of one or more substituents, phenyl or naphthyl, is selected to be substituted by one or more substituents from the group consisting of free fluorine atom, methyl and cyano group;

[0214] Ar 2 It indicates a phenyl or naphthyl group that is substituted with one or more substituents from the group consisting of a free fluorine atom, a methyl group, and a cyano group.

[0215] [About A]

[0216] A represents a phenyl, biphenyl, or naphthyl group that is substituted with one or more groups selected from the group consisting of a fluorine atom, a methyl group, and a cyano group. From the viewpoint of easily synthesizing triazine compounds represented by formula Z(1) (hereinafter also referred to as triazine compound Z(1)), A is preferably an unsubstituted phenyl, biphenyl, or naphthyl group, and more preferably an unsubstituted phenyl or biphenyl group.

[0217] [About B]

[0218] B represents a phenyl, biphenyl, or naphthyl group that is substituted with one or more groups selected from the group consisting of a fluorine atom, a methyl group, and a cyano group. From the viewpoint of easily synthesizing triazine compound Z(1), B is preferably an unsubstituted phenyl, biphenyl, or naphthyl group, and more preferably an unsubstituted phenyl or biphenyl group.

[0219] [About Ar]1 ]

[0220] Ar 1 This indicates a phenyl or naphthyl group, substituted with one or more substituents from the group consisting of a free fluorine atom, methyl group, and cyano group. From the viewpoint of easily synthesizing triazine compound Z(1), Ar 1 Preferably, it is an unsubstituted phenyl or naphthyl group, more preferably an unsubstituted phenyl group.

[0221] [About Ar] 2 ]

[0222] Ar 2 This indicates a phenyl or naphthyl group, substituted with one or more substituents from the group consisting of a free fluorine atom, methyl group, and cyano group. From the viewpoint of easily synthesizing triazine compound Z(1), Ar 2 Preferably, it is an unsubstituted phenyl or naphthyl group.

[0223] [Specific examples of triazine compound Z(1)]

[0224] Specific examples of particularly preferred compounds among the triazine compounds described in one aspect of the present invention as shown in formula Z(1) are the compounds shown in formulas Z(1-1) to Z(1-95) below, but the triazine compounds described in one aspect of the present invention are not limited to them.

[0225]

[0226]

[0227]

[0228]

[0229]

[0230] The uses of triazine compound (1) will be described below.

[0231] Materials for Organic Electroluminescent Devices, Electron Transport Materials for Organic Electroluminescent Devices

[0232] Triazine compound (1) is not particularly limited and can be used, for example, as a material for organic electroluminescent devices. In addition, triazine compound (1) can be used, for example, as an electron transport material for organic electroluminescent devices.

[0233] That is, the organic electroluminescent element material according to one aspect of the present invention comprises a triazine compound (1). Additionally, the electron transport material for the organic electroluminescent element according to one aspect of the present invention comprises a triazine compound (1). The organic electroluminescent element material comprising a triazine compound (1) and the electron transport material for the organic electroluminescent element contribute to the fabrication of organic electroluminescent elements with excellent driving voltage characteristics and current efficiency.

[0234] Organic electroluminescent elements

[0235] The organic electroluminescent element of one embodiment of the present invention comprises a triazine compound (1).

[0236] There are no particular limitations on the structure of organic electroluminescent elements, but examples such as (i) to (vi) shown below can be cited.

[0237] (i): Anode / Light-emitting layer / Cathode

[0238] (ii): Anode / Hole Transport Layer / Light Emitting Layer / Cathode

[0239] (iii): Anode / Emitting Layer / Electron Transport Layer / Cathode

[0240] (iv): Anode / Hole Transport Layer / Emitting Layer / Electron Transport Layer / Cathode

[0241] (v): Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0242] (vi): Anode / hole injection layer / charge generation layer / hole transport layer / light emission layer / electron transport layer / cathode.

[0243] Hereinafter, with regard to an organic electroluminescent element according to one aspect of the present invention, the above-described (vi) configuration will be listed as an example, while referring to... Figure 1 Let me explain in more detail. Figure 1 This is a schematic cross-sectional view illustrating an example of a stacked configuration of an organic electroluminescent element comprising a triazine compound as described in one aspect of the present invention.

[0244] It should be noted that, Figure 1 The organic electroluminescent element shown has a so-called bottom-emitting type element configuration, but the organic electroluminescent element described in one aspect of the present invention is not limited to a bottom-emitting type element configuration. That is, the organic electroluminescent element described in one aspect of the present invention can be a top-emitting type element configuration, or it can be other known element configurations.

[0245] The organic electroluminescent element 100 sequentially comprises a substrate 1, an anode 2, a hole injection layer 3, a charge generation layer 4, a hole transport layer 5, a light-emitting layer 6, an electron transport layer 7, and a cathode 8. Some of these layers may be omitted, or other layers may be added. For example, an electron injection layer may be disposed between the electron transport layer 7 and the cathode 8, or the charge generation layer 4 may be omitted, and the hole transport layer 5 may be directly disposed on the hole injection layer 3.

[0246] Alternatively, a single layer that combines the functions of both an electron injection layer and an electron transport layer can be used instead of multiple layers. Furthermore, for example, the single-layer hole transport layer 5 and the single-layer electron transport layer 7 can each be composed of multiple layers.

[0247] [A layer containing the triazine compound shown in formula (1)]

[0248] The light-emitting layer of the organic electroluminescent element and one or more layers selected from the group consisting of the light-emitting layer and the layer between the light-emitting layer and the cathode contain a triazine compound as shown in formula (1) above. Therefore, in Figure 1 In the example shown, at least one layer of the organic electroluminescent element 100 selected from the group consisting of the light-emitting layer 6 and the electron transport layer 7 contains a triazine compound (1).

[0249] In particular, the electron transport layer 7 preferably contains a triazine compound (1). It should be noted that the triazine compound (1) may be contained in multiple layers of the organic electroluminescent element, and when an electron injection layer is provided between the electron transport layer and the cathode, the electron injection layer may contain the triazine compound (1).

[0250] It should be noted that the following description pertains to an organic electroluminescent element 100 in which the electron transport layer 7 contains a triazine compound (1).

[0251] [Substrate 1]

[0252] There are no particular limitations on the substrate; examples include glass plates, quartz plates, and plastic plates. Furthermore, in the case where the light is emitted from the substrate 1 side, the substrate 1 is transparent with respect to the wavelength of the light.

[0253] Examples of transparent plastic films include those made from polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC), cellulose triacetate (TAC), and cellulose acetate propionate (CAP).

[0254] [Anode 2]

[0255] An anode 2 is disposed on the substrate 1 (on the side of the hole injection layer 3).

[0256] In the case of an organic electroluminescent element that emits light through an anode, the anode is formed of a material through which the light is emitted or substantially emitted.

[0257] There are no particular limitations on the transparent materials used as anodes, and examples include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide, aluminum-doped tin oxide, magnesium indium oxide, nickel tungsten oxide, other metal oxides, metal nitrides such as gallium nitride, metal selenides such as zinc selenide, and metal sulfides such as zinc sulfide.

[0258] It should be noted that in the case of organic electroluminescent devices that extract light only from the cathode side, the transmittance characteristics of the anode are not important. Therefore, examples of materials used for the anode in this case include gold, iridium, molybdenum, palladium, and platinum.

[0259] A buffer layer (electrode interface layer) can be set on the anode.

[0260] [Hole injection layer 3, hole transport layer 5]

[0261] Between the anode 2 and the light-emitting layer 6 (described later), starting from the anode 2 side, a hole injection layer 3, a charge generation layer 4 (described later), and a hole transport layer 5 are sequentially arranged.

[0262] The hole injection layer and hole transport layer have the function of conducting holes injected from the anode to the light-emitting layer. By sandwiching the hole injection layer and hole transport layer between the anode and the light-emitting layer, a large number of holes are injected into the light-emitting layer under a lower electric field.

[0263] Furthermore, the hole injection layer and hole transport layer also function as electron barrier layers. That is, by utilizing the electron potential barrier present at the interface between the light-emitting layer and the hole injection layer and / or hole transport layer, leakage of electrons injected from the cathode and transported from the electron injection layer and / or electron transport layer to the light-emitting layer is suppressed. As a result, these electrons accumulate at the interface within the light-emitting layer, leading to improved current efficiency and other effects, resulting in an organic electroluminescent device with excellent light-emitting performance.

[0264] The material used for the hole injection layer and hole transport layer possesses at least one of the following: hole injection property, hole transport property, and electron barrier property. The material for the hole injection layer and hole transport layer can be any of organic or inorganic materials.

[0265] Specific examples of materials for the hole injection layer and hole transport layer include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolineone derivatives, phenylenediamine derivatives, aromatic amine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrene-anthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers (especially thiophene oligomers), porphyrin compounds, aromatic tertiary amine compounds, and styrene-based amine compounds. Among these, porphyrin compounds, aromatic tertiary amine compounds, and styrene-based amine compounds are preferred, and aromatic tertiary amine compounds are particularly preferred.

[0266] Specific examples of aromatic tertiary amine compounds and styrylamine compounds include N,N,N',N'-tetraphenyl-4,4'-diaminophenyl, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1'-biphenyl]-4,4'-diamine (TPD), 2,2-bis(4-di-p-tolylaminophenyl)propane, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl, 1,1-bis(4-di-p-tolylaminophenyl)-4-phenylcyclohexane, bis(4-dimethylamino-2-methylphenyl)phenylmethane, bis(4-di-p-tolylaminophenyl)phenylmethane, N,N'-diphenyl- N,N'-Di(4-methoxyphenyl)-4,4'-diaminobiphenyl, N,N,N',N'-tetraphenyl-4,4'-diaminodiphenyl ether, 4,4'-bis(diphenylamino)tetraphenyl, N,N,N-tris(p-tolyl)amine, 4-(dip-tolylamino)-4'-[4-(dip-tolylamino)styryl]stilbene, 4-N,N-diphenylamino-(2-diphenylvinyl)benzene, 3-methoxy-4'-N,N-diphenylaminostyrylbenzene, N-phenylcarbazole, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPD), 4,4',4”-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), etc.

[0267] In addition, inorganic compounds such as p-type-Si and p-type-SiC can also be cited as examples of materials for hole injection layers and hole transport layers.

[0268] Hole injection layer and hole transport layer can be a single-layer structure formed by one or more materials, or a stacked structure formed by multiple layers with the same composition or different compositions.

[0269] [Charge Generation Layer 4]

[0270] A charge generation layer 4 can be set between the hole injection layer 3 and the hole transport layer 5.

[0271] The material used as the charge-generating layer is not particularly limited, but examples include dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile (HAT-CN).

[0272] The charge generation layer can be a single-layer structure formed by one or more materials, or it can be a stacked structure formed by multiple layers with the same composition or different compositions.

[0273] [Emitting Layer 6]

[0274] A light-emitting layer 6 is disposed between the hole transport layer 5 and the electron transport layer 7 (described later).

[0275] Materials used as luminescent layers include phosphorescent materials, fluorescent materials, and thermally activated delayed fluorescence materials. In the luminescent layer, electron / hole pairs recombine, resulting in luminescence.

[0276] The luminescent layer can be formed from a single low-molecular-weight material or a single polymer material, but more commonly, it is formed from a host material doped with guest compounds. Emission is primarily generated by the dopant and can have any color.

[0277] Examples of main materials include compounds containing biphenyl, fluorenyl, triphenylsilyl, carbazole, pyrene, and anthracene groups. More specifically, examples include DPVBi (4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl), BCzVBi (4,4'-bis(9-ethyl-3-carbazole-vinylene)-1,1'-biphenyl), TBADN (2-tert-butyl-9,10-bis(2-naphthyl)anthracene), ADN (9,10-bis(2-naphthyl)anthracene), CBP (4,4'-bis(carbazole-9-yl)biphenyl), CDBP (4,4'-bis(carbazole-9-yl)-2,2'-dimethylbiphenyl), 2-(9-phenylcarbazole-3-yl)-9-[4-(4-phenylphenylquinazolin-2-yl)carbazole], and 9,10-bis(biphenyl)anthracene.

[0278] Examples of fluorescent dopants include anthracene, pyrene, tetraphenylene, xanthones, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyran compounds, thiaran compounds, polyacetylenes, pyranonium, thiaranonium compounds, fluorene derivatives, diindronepyrene derivatives, indolebenzene derivatives, bis(acrazinyl)amineboron compounds, bis(acrazinyl)methane compounds, and quinolone compounds. Fluorescent dopants can also be combinations of two or more selected from these.

[0279] Examples of phosphorescent dopants include organometallic complexes of transition metals such as iridium, platinum, palladium, and osmium.

[0280] Specific examples of fluorescent and phosphorescent dopants include Alq3 (tris(8-hydroxyquinoline)aluminum), DPAVBi (4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl), perylene, bis[2-(4-n-hexylphenyl)quinoline](acetylacetone)iridium(III), Ir(PPy)3 (tris(2-phenylpyridine)iridium(III)) and FIrPic (bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(III))).

[0281] Furthermore, the luminescent material is not limited to being contained only in the luminescent layer. For example, the layer adjacent to the luminescent layer (hole transport layer 5 or electron transport layer 7) may also contain the luminescent material. This can further improve the current efficiency of the organic electroluminescent device.

[0282] The light-emitting layer can be a single-layer structure formed by one or more materials, or it can be a stacked structure formed by multiple layers with the same composition or different compositions.

[0283] [Electron transport layer 7]

[0284] An electron transport layer 7 is disposed between the light-emitting layer 6 and the cathode 8 (described later).

[0285] The electron transport layer functions to transport electrons injected from the cathode to the light-emitting layer. By sandwiching the electron transport layer between the cathode and the light-emitting layer, electrons can be injected into the light-emitting layer under a lower electric field.

[0286] As described above, the electron transport layer preferably contains a triazine compound represented by formula (1).

[0287] In addition, the electron transport layer may contain, in addition to the triazine compound (1), existing known electron transport materials. Examples of existing known electron transport materials include, for instance, lithium 8-hydroxyquinoline (Liq), bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)gallium chloride, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)-1-naphthol aluminum or bis(2-methyl-8-quinoline)- Gallium 2-naphthol, 2-[3-(9-phenanthyl)-5-(3-pyridyl)phenyl]-4,6-diphenyl-1,3,5-triazine and 2-(4,”-di-2-pyridyl[1,1':3',1”-terphenyl]-5-yl)-4,6-diphenyl-1,3,5-triazine, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), BAlq (bis(2-methyl-8-hydroxyquinoline)-4-(phenylphenol)aluminum) and bis(10-hydroxybenzo[h]quinoline)beryllium), etc.

[0288] The electron transport layer can be a single-layer structure made of one or more materials, or it can be a stacked structure made of multiple layers with the same or different compositions.

[0289] In the case where the electron transport layer is a two-layer structure in which the first electron transport layer is formed on the light-emitting layer side and the second electron transport layer is formed on the cathode side, the second electron transport layer preferably contains a triazine compound (1).

[0290] [Cathode 8]

[0291] A cathode 8 is disposed on the electron transport layer 7.

[0292] In the case of an organic electroluminescent element that extracts only the light emitted through the anode, the cathode can be formed of any conductive material.

[0293] Materials that can be used as cathodes include sodium, sodium-potassium alloys, magnesium, lithium, magnesium / copper mixtures, magnesium / silver mixtures, magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / alumina (Al2O3) mixtures, indium, lithium / aluminum mixtures, rare earth metals, etc.

[0294] A buffer layer (electrode interface layer) can be set on the cathode (on the electron transport layer side).

[0295] [Methods of forming each layer]

[0296] Other than the electrodes (anode and cathode) described above, each layer can be formed by thinning the material of each layer (together with materials such as adhesive resin and solvent, as needed) using known methods such as vacuum evaporation, spin coating, casting, and the LB (Langmuir-Blodgett method).

[0297] There is no particular limitation on the thickness of the films formed by such operation; it can be selected appropriately according to the situation, usually in the range of 5nm to 5μm.

[0298] Anodes and cathodes can be formed by thin-film deposition of electrode materials using methods such as evaporation and sputtering. Patterns can be formed through a mask of the desired shape during evaporation and sputtering, or patterns of the desired shape can be formed by photolithography after thin films have been formed using evaporation and sputtering.

[0299] The film thickness of the anode and cathode is preferably less than 1 μm, more preferably more than 10 nm and less than 200 nm.

[0300] The organic electroluminescent element described in one aspect of the present invention can be used as a lamp for illumination or exposure, or as a projection device for projecting images, or a display device (monitor) for directly viewing still or moving images. When used as a video playback display device, the driving method can be a simple matrix (passive matrix) or an active matrix. Furthermore, by using two or more organic electroluminescent elements of this embodiment with different emission colors, a full-color display device can be manufactured.

[0301] It should be noted that the triazine compound (1) described in one aspect of the present invention can be synthesized by appropriately combining known reactions (e.g., Suzuki-Miyaura crosslinking coupling reaction, etc.).

[0302] Example

[0303] The present invention will now be described in more detail with reference to embodiments, but the present invention is not limited to any of these embodiments.

[0304] 1 H-NMR measurements were performed using a Gemini200 (manufactured by Varian).

[0305] FDMS measurements were performed using an M-80B manufactured by Hitachi.

[0306] The glass transition temperature was measured using a DSC7020 (manufactured by Hitachi High-Tech Co., Ltd.).

[0307] For DSC determination, aluminum oxide (Al2O3) was used as the reference, and the determination was performed using 10 mg of sample.

[0308] As a pretreatment for the determination, the sample was melted by heating it from 30°C to a temperature above its melting point at a rate of 10°C / min, and then the sample was quenched by contacting dry ice. Next, the pretreated sample was heated from 30°C to a temperature above its melting point at a rate of 10°C / min, and the glass transition temperature was measured.

[0309] The luminescence characteristics of the organic electroluminescent element were evaluated by applying a direct current to the fabricated element at room temperature (23°C, 50% RH) and using a luminance meter (product name: BM-9, manufactured by TOPCON TECHNOHOUSE).

[0310] <Triazine compound X(1)>

[0311] Synthesis Example 1: Synthesis of Compound X (1-2)

[0312]

[0313] Under a nitrogen atmosphere, 1,4-dioxane (69 ml) was added to a flask containing 1-chloro-2,5-di(naphthyl-2-yl)benzene (5.0 g, 13.7 mmol), bis(pinacol)diboron (5.2 g, 20.6 mmol), PdCl2[(Pcy3)]2 (202 mg, 0.27 mmol), and potassium acetate (4.0, 41.1 mmol). The mixture was stirred at 100 °C for 21 hours. After cooling to room temperature, the solid was collected from the reaction solution by filtration and washed with 1,4-dioxane. The solid was recrystallized from a methanol (100 ml) solution to give 2-[2,5-di(naphthyl-2-yl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborane (5.1 g yield).

[0314] Tetrahydrofuran (191 ml) was added to a flask containing 2-chloro-4,6-bis(biphenyl-4-yl)-1,3,5-triazine (4.0 g, 9.5 mmol), 2-[2,5-bis(naphth-2-yl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborane (4.8 g, 10.5 mmol), and Pd(PPh3)4 (220 mg, 0.19 mmol) under a nitrogen atmosphere. Then, 2M potassium phosphate aqueous solution (14 ml, 28.6 mmol) was added, and the mixture was stirred at 70°C for 22 hours. After natural cooling to room temperature, the precipitated solid was collected by vacuum filtration and washed with water and acetone. The solid was dissolved in toluene (2000 ml), activated carbon (1.2 g) was added, and the mixture was heated and stirred at 100°C for 1 hour. Activated carbon was filtered off using a Kiriyama funnel containing Celite, and recrystallized from the filtrate to obtain a white solid of compound X(1-2) (yield 4.5 g). The glass transition temperature was 116 °C.

[0315] 1 H-NMR (CDCl3) δ (ppm): 8.85 (m, 1H), 8.26 (m, 5H), 7.90-8.10 (m, 7H), 7.72-7.86 (m, 3H), 7.44-7.65 (m, 16H), 7.39 (m, 3H).

[0316] Synthesis Example 2: Synthesis of Compound X (1-4)

[0317]

[0318] Tetrahydrofuran (110 mL) was added to a flask containing 2-chloro-4,6-bis(biphenyl-4-yl)-1,3,5-triazine (2.3 g, 5.5 mmol), 2-[4-(9-phenanthroline)[1,1'-biphenyl]-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborane (3.0 g, 6.57 mmol), and Pd(PPh3)4 (127 mg, 0.11 mmol) under a nitrogen atmosphere. Then, 2 M potassium phosphate aqueous solution (8 mL, 16.4 mmol) was added, and the mixture was stirred at 70 °C for 20 hours. After natural cooling to room temperature, water and toluene were added for separation. After the solvent was removed by vacuum distillation, water was added, and the precipitated solid was collected by filtration. The solid was washed with water and acetone. The resulting solid was dissolved in toluene (250 ml), and activated carbon (0.4 g) was added. The mixture was heated and stirred at 100 °C for 1 hour. The activated carbon was filtered off by vacuum filtration through a Kiriyama funnel containing Celite, and the solvent was removed by vacuum distillation. Recrystallization from the toluene / 1-butanol mixture yielded a white solid of compound X(1-4) (yield 1.5 g). The glass transition temperature was 137 °C.

[0319] 1 H-NMR(CDCl3)δ(ppm): 8.84(d,1H),8.78(d,1H),8.56(m,1H),8.40(m,4H),8.10(d, 1H),7.98(d,1H),7.87(s,1H),7.81(m,1H),7.58-7.73(m,13H),7.31-7.50(m,11H).

[0320] Synthesis Example 3: Synthesis of Compound X (1-5)

[0321]

[0322] The 2-[4-(9-phenanthyl)[1,1'-biphenyl]-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborane was replaced with 2-[4-(naphthyl-2-yl)[1,1'-biphenyl]-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborane. Otherwise, the same experimental procedures as in Example-2 of X synthesis were performed to obtain a white solid of compound X(1-5) (yield 2.5 g).

[0323] FDMS: 663

[0324] Synthesis Example 4: Synthesis of Compound X (1-75)

[0325]

[0326] The 2-[4-(9-phenanthyl)[1,1'-biphenyl]-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborane was replaced with 2-[4-(naphthyl-2-yl)[1,1':4',1”-terphenyl]-2'-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborane. Otherwise, the same experimental procedures as in Example-2 of X synthesis were performed to obtain a white solid of compound X(1-75) (yield 1.4 g).

[0327] 1 H-NMR (CDCl3) δ (ppm): 8.69 (d, J = 2.0Hz, 1H), 8.47-8.41 (m, 5H), 8.03 (d, J = 9.2Hz, 1H), 7.96-7.88 (m, 5H), 7.7 2(dd,J=3.6Hz,3.6Hz,2H),7.69-7.61(m,8H),7.58-7.54(m,2H),7.52(brd,J=1.6Hz,1H),7.50-7.37(m,12H).

[0328] Synthesis Example 5: Synthesis of Compound X (1-80)

[0329]

[0330] The 2-chloro-4,6-bis(biphenyl-4-yl)-1,3,5-triazine was replaced with 6-chloro-2-[(1,1'-biphenyl)-2-yl]-4-[(1,1'-biphenyl)-4-yl]-1,3,5-triazine. Otherwise, the same experimental procedures as in Example-2 of the synthesis of X were performed to obtain a white solid of compound X(1-80) (yield 3.0 g). The glass transition temperature of compound X(1-80) was 125 °C.

[0331] 1 H-NMR(CDCl3)δ(ppm): 8.86(d,J=9.2Hz,1H),8.81(d,J=8.0Hz,1H),7.98(brd,J=6.0Hz,1H),7.88(brd,J=8.0Hz,1H),7.84-7.79(m,2H),7.79(d,J=1 .6Hz,1H),7.76-7.66(m,5H),7.63-7.57(m,4H),7.54-7.32(m,14H),7.13( dd,J=8.0Hz,1.2Hz,2H),6.81(brt,J=7.2Hz,2H),6.42(brt,J=7.6Hz,1H).

[0332] <Triazine compound Y(1)>

[0333] Example 1: Synthesis of compound Y (1-96)

[0334]

[0335] Tetrahydrofuran (170 mL) was added to a flask containing 2,4-bis([1,1'-biphenyl]-4-yl)-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenyl]-1,3,5-triazine (10.0 g, 17.02 mmol), 2,3-dichlorobromobenzene (4.2 g, 18.72 mmol), and Pd(PPh3)4 (393 mg, 0.34 mmol) under a nitrogen atmosphere. Then, 2M potassium phosphate aqueous solution (25.5 mL, 51.06 mmol) was added, and the mixture was stirred at 70 °C for 24 hours. After natural cooling to room temperature, the precipitated solid was collected by vacuum filtration, washed with water, and then washed with methanol. After dissolving the resulting solid in toluene, it was recrystallized to obtain 2,4-bis([1,1'-biphenyl]-4-yl)-6-(2',3'-dichloro[1,1'-biphenyl]-4-yl-1,3,5-triazine (yield 9.1 g, 88%).

[0336] Tetrahydrofuran (300 ml) was added to a flask containing 2,4-bis([1,1'-biphenyl]-4-yl)-6-(2',3'-dichloro[1,1'-biphenyl]-4-yl-1,3,5-triazine (9.1 g, 15.05 mmol), phenylboronic acid (12.8 g, 105.4 mmol), palladium acetate (68 mg, 0.30 mmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (X-Phos) (287 mg, 0.60 mmol) under a nitrogen gas flow. Then, 2M potassium phosphate aqueous solution (38 ml) was added. The mixture was stirred at 70°C for 90 hours. After natural cooling to room temperature, the precipitated solid was collected by vacuum filtration and washed with water and ethanol. The resulting solid was dissolved in toluene (1000 mL), and activated carbon (1.2 g) was added. The mixture was heated and stirred at 100°C for 2 hours. The activated carbon was filtered through a Kiriyama funnel containing Celite, and the filtrate was removed by vacuum distillation. Recrystallization from the toluene (800 mL) solution yielded a white solid of compound Y(1-96) (6.9 g, 66% yield). The glass transition temperature was 158°C.

[0337] 1H-NMR(CDCl3)δ(ppm): 8.83(d,4H),8.62(d,2H),7.80(d,4H),7.71(d,4H),7.47-7.57(m,7H),7 .42(m,2H),7.32(d,2H),7.17(m,3H),7.08-7.13(m,2H),6.98-7.05(m,3H),6.89-6.94(m,2H).

[0338] Synthesis Example 2: Synthesis of Compound Y (1-180)

[0339]

[0340] Tetrahydrofuran (270 ml) was added to a flask containing 2-[(1,1'-biphenyl)-4-yl]-4-(naphth-2-yl)-6-[3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenyl]-1,3,5-triazine (15.0 g, 26.7 mmol), {(1,1':2',1”-triphenyl)-3'-yl}trifluoromethanesulfonate (11.1 g, 29.4 mmol), and Pd(PPh3)4 (927 mg, 0.801 mmol) under a nitrogen gas flow. Then, 2M potassium phosphate aqueous solution (40.1 ml, 8 ml) was added. 0.2 mmol) was added and stirred at 70 °C for 26 hours. After natural cooling to room temperature, the precipitated solid was collected by vacuum filtration and washed with water and acetone. The solid was dissolved in chlorobenzene (800 ml), and activated carbon (3.2 g) was added. The mixture was heated and stirred at 100 °C for 1 hour. The activated carbon was collected by vacuum filtration using a Kiriyama funnel containing Celite, and the filtrate was removed by vacuum distillation. Recrystallization from the chlorobenzene (700 ml) solution yielded a white solid of compound Y(1-180) (yield 13.9 g). The glass transition temperature of compound Y(1-180) is 11 °C.

[0341] 1H-NMR(CDCl3)δ(ppm): 6.95-7.04(m,5H),7.14-7.23(m,5H),7.31-7.33(m,1 H),7.38-7.45(m,2H),7.50-7.65(m,7H),7.74(d,J=7.7Hz,2H),7.83(d,J=8. 5Hz,2H),7.94-7.96(m,1H),8.03(d,J=8.7Hz,1H),8.11-8.13(m,1H),8.64-8 .67(m,2H),8.8(dd,J=8.5Hz,1.7Hz,1H),8.86(d,J=8.7Hz,2H),9.32(s,1H).

[0342] <Triazine compound Z(1)>

[0343] Example 1: Synthesis of Compound Z(1-2)

[0344]

[0345] Under a nitrogen atmosphere, tetrahydrofuran (51 ml) was added to a flask containing 2,4-bis[(1,1'-biphenyl)-4-yl]-6-[3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenyl]-1,3,5-triazine (3.0 g, 5.1 mmol), {(1,1':3',1”-terphenyl)-4'-yl}trifluoromethanesulfonate (2.1 g, 5.6 mmol), and Pd(PPh3)4 (133 mg, 0.12 mmol). Then, 2 M potassium phosphate aqueous solution (7.5 mL) was added. 7 ml (16.0 mmol) was stirred at 70 °C for 20 hours. After natural cooling to room temperature, the precipitated solid was collected by vacuum filtration and washed with water and acetone. The solid was dissolved in toluene (500 ml), and activated carbon (0.5 g) was added. The mixture was heated and stirred at 100 °C for 1 hour. The activated carbon was collected by vacuum filtration using a Kiriyama funnel containing Celite. Recrystallization from the filtrate yielded a white solid of compound Z(1-2) (3.0 g yield). The glass transition temperature of compound Z(1-2) is 119 °C.

[0346] 1 H-NMR (CDCl3) δ (ppm): 8.84-8.79 (m, 4H), 8.71 (t, J = 12.0Hz, 1H), 8.64-8.69 (m, 1 H),7.79-7.84(m,4H),7.68-7.77(m,9H),7.27-7.67(m,15H),7.18-7.24(m,1H).

[0347] Synthesis Example 2 - Synthesis of Compound Z (1-13)

[0348]

[0349] The 2,4-bis[(1,1'-biphenyl)-4-yl]-6-[3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenyl]-1,3,5-triazine was replaced with 2-[(1,1'-biphenyl)-2-yl]-4-[(1,1'-biphenyl)-4-yl]-6-[3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenyl]-1,3,5-triazine. Otherwise, the same experimental procedures as in Example-1 of the Z synthesis were performed to obtain compound Z(1-13) as a white solid (yield 4.4 g). The glass transition temperature of compound Z(1-13) was 107 °C.

[0350] FDMS: 689

[0351] Synthesis Example 3 - Synthesis of Compound Z (1-15)

[0352]

[0353] The 2,4-bis[(1,1'-biphenyl)-4-yl]-6-[3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenyl]-1,3,5-triazine was replaced with 2-[(1,1'-biphenyl)-2-yl]-6-(naphthyl)-4-[3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenyl]-1,3,5-triazine. Otherwise, the same experimental procedures as in Example-1 of the Z synthesis were performed to obtain compound Z(1-15) as a white solid (yield 9.7). The glass transition temperature of compound Z(1-15) was 112 °C.

[0354] 1 H-NMR (CDCl3) δ (ppm): 7.20 (t, J = 7.4Hz, 1H), 7.28 (t, J = 7.3Hz, 2H), 7.33-7.53 (m, 10H),7.56-7.63(m,2H),7.70-7.77(m,7H),7.83(d,J=8.6Hz,2H),7.94-7.96(m,1 H),8.02(d,J=8.7Hz,1H),8.11-8.13(m,1H),8.70(dt,J=7.4Hz,1.7Hz,1H),8.75( t,J=1.5Hz,1H),8.79(dd,J=8.7Hz,1.5Hz,1H),8.85(d,J=8.5Hz,2H),9.31(s,1H).

[0355] Next, the obtained compound is used to perform device evaluation.

[0356] <X Device Example - 1 (Reference Figure 2 <000001]])>

[0357] (Preparation of Substrate 101 and Anode 102)

[0358] As a substrate having an anode on its surface, a glass substrate with an ITO transparent electrode is prepared by patterning a 2 - mm - wide indium tin oxide (ITO) film (film thickness: 110 nm) into a striped shape. Next, the substrate is cleaned with isopropyl alcohol and then surface - treated by ozone - ultraviolet cleaning.

[0359] (Preparation for Vacuum Evaporation)

[0360] On the cleaned and surface - treated substrate, vacuum evaporation of each layer is carried out by the vacuum evaporation method to form each layer by lamination.

[0361] First, the aforementioned glass substrate is introduced into the vacuum evaporation chamber, and the pressure is reduced to 1.0×10 -4 Pa. And, according to the film - forming conditions of each layer, they are fabricated in the following order.

[0362] (Fabrication of Hole - Injection Layer 103)

[0363] Sublimation - purified N - [1,1'-biphenyl]-4 - yl - 9,9 - dimethyl - N - [4-(9 - phenyl - 9H - carbazol - 3 - yl)phenyl]-9H - fluorene - 2 - amine and 1,2,3 - tris[(4 - cyano - 2,3,5,6 - tetrafluorophenyl)methylene]cyclopropane are formed into a 10 - nm film at a speed of 0.15 nm / second to fabricate the hole - injection layer 103.

[0364] (Fabrication of First Hole - Transport Layer 1051)

[0365] Sublimation - purified N - [1,1'-biphenyl]-4 - yl - 9,9 - dimethyl - N - [4-(9 - phenyl - 9H - carbazol - 3 - yl)phenyl]-9H - fluorene - 2 - amine is formed into an 85 - nm film at a speed of 0.15 nm / second to fabricate the first hole - transport layer 1051.

[0366] (Fabrication of Second Hole - Transport Layer 1052)

[0367] Sublimation - purified N - phenyl - N - (9,9 - diphenylfluorene - 2 - yl)-N - (1,1'-biphenyl - 4 - yl)amine is formed into a 5 - nm film at a speed of 0.15 nm / second to fabricate the second hole - transport layer 1052.

[0368] Through the above operations, a hole transport layer 105 consisting of two stacked layers, namely a first hole transport layer 1051 and a second hole transport layer 1052, is fabricated.

[0369] (Fabrication of the luminescent layer 106)

[0370] Sublimated and purified 3-(10-phenyl-9-anthrayl)dibenzofuran and 2,7-bis[N,N-bis(4-tert-butylphenyl)]amino-bisbenzofuranyl-9,9'-spirofluorene were mixed in a 95:5 (mass ratio) to form a 20 nm emissive layer, 106. The deposition rate was 0.18 nm / s.

[0371] (Fabrication of the first electron transport layer 1071)

[0372] The first electron transport layer 1071 was fabricated by depositing a 6 nm thick film of 2-[3'-(9,9-dimethyl-9H-fluorene-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine at a rate of 0.05 nm / s.

[0373] (Fabrication of the second electron transport layer 1072)

[0374] Compounds X(1-2) synthesized in Example X-1 and Liq were mixed in a 50:50 (mass ratio) to form a 25 nm film, which was used to create the second electron transport layer 1072. The film formation rate was 0.15 nm / s.

[0375] Through the above operations, an electron transport layer 107 consisting of a first electron transport layer 1071 and a second electron transport layer 1072 is fabricated.

[0376] (Fabrication of cathode 108)

[0377] Finally, a metal mask is configured orthogonally to the ITO stripes on the substrate to form the cathode 108. The cathode is formed by sequentially depositing silver / magnesium (mass ratio 1 / 10) and silver at 80 nm and 20 nm, respectively, to create a two-layer structure. The deposition rate of silver / magnesium is 0.5 nm / s, and the deposition rate of silver is 0.2 nm / s.

[0378] Through the above operations, create Figure 2 The light-emitting area shown is 4mm². 2 Organic electroluminescent element 100. It should be noted that the film thickness of each element was measured using a stylus-type film thickness gauge (DEKTAK, Bruker).

[0379] Furthermore, the component is sealed in a nitrogen atmosphere glove box with oxygen and moisture concentrations below 1 ppm. A bisphenol F type epoxy resin (manufactured by Nagase ChemteX Corporation) is used to seal the glass sealing cover and the film-forming substrate (component).

[0380] A direct current is applied to the organic electroluminescent device fabricated as described above, and a luminance meter (product name: BM-9, manufactured by TOPCON TECHNOHOUSE Corporation) is used to evaluate the luminescence characteristics. As the luminescence characteristics, the current efficiency (cd / A), driving voltage (V), and device life (h) during continuous lighting are measured when the current density flowing through is 10 mA / cm 2 . Regarding the device life (h), the luminance decay time during continuous lighting when the fabricated device is driven at an initial luminance of 1000 cd / m 2 is measured, and the time required until the luminance (cd / m 2 ) decreases by 5% is measured.

[0381] It should be noted that the current efficiency, driving voltage, and device life (h) in Tables 1 to 3 are represented by relative values obtained by taking the results in Reference Example 1 of Component X, Reference Example 1 of Component Y, and Reference Example 1 of Component Z as reference values (100). The obtained measurement results are shown in Tables 1 to 3.

[0382] <Example of Component X - 2>

[0383] In Example of Component X - 1, Compound X(1 - 4) is used instead of Compound X(1 - 2). Except for this, an organic electroluminescent device is fabricated and evaluated in the same manner as in Example of Component X - 1. The obtained measurement results are shown in Table 1.

[0384] <Example of Component X - 3>

[0385] In Example of Component X - 1, Compound X(1 - 5) synthesized in Synthesis Example X - 3 is used instead of Compound X(1 - 2). Except for this, an organic electroluminescent device is fabricated and evaluated in the same manner as in Example of Component X - 1. The obtained measurement results are shown in Table 1.

[0386] <Example of Component X - 4>

[0387] In Example of Component X - 1, Compound X(, synthesized in Synthesis Example X - 4 is used instead of Compound X(1 - 2). Except for this, an organic electroluminescent device is fabricated and evaluated in the same manner as in Example of Component X - 1. The obtained measurement results are shown in Table 1.

[0388] <Example of Component X - 5>

[0389] In X-Element Example-1, the compound X(1-80) synthesized in X-Synthesis Example-5 was used to replace the compound X(1-2). Except for this, an organic electroluminescent element was fabricated and evaluated using the same method as in X-Element Example-1. The obtained measurement results are shown in Table 1.

[0390] <X-Element Reference Example-1>

[0391] In X-Element Example-1, the compound 24 described in Patent Document 1 was used to replace the compound X(1-2). Except for this, an organic electroluminescent element was fabricated and evaluated using the same method as in X-Element Example-1. The obtained measurement results are shown in Table 1.

[0392]

[0393] [Table 1]

[0394] compound Current efficiency Drive voltage life X-Element Example 1 1-2 100 98 130 X-Element Example 2 1-4 100 95 150 X-Element Example 3 1-5 101 95 160 X-Element Example 4 1-75 100 96 155 X-Element Example 5 1-80 106 99 115 X-Component Reference Example-1 Compound 24 100 100 100

[0395] <Y-Element Example-1 (Reference Figure 2 )>

[0396] In X-Element Example-1, the compound Y(1-96) synthesized in Y-Synthesis Example-1 was used to replace the compound X(1-2). Except for this, an organic electroluminescent element was fabricated and evaluated using the same method as in X-Element Example-1. The obtained measurement results are shown in Table 2.

[0397] <Y-Element Example-2 (Reference Figure 2 )>

[0398] In X-Element Example-1, the compound Y(1-180) synthesized in Y-Synthesis Example-2 was used to replace the compound X(1-2). Except for this, an organic electroluminescent element was fabricated and evaluated using the same method as in X-Element Example-1. The obtained measurement results are shown in Table 2.

[0399] <Y-Element Reference Example-1> ]]

[0400] In Y-Element Example-1, the compound disclosed in Example-9 of Patent Document 2 (Japanese Unexamined Patent Application Publication No. 2018-95562) was used to replace the compound Y(1-96). Except for this, an organic electroluminescent element was fabricated and evaluated using the same method as in X-Element Example-1. The obtained measurement results are shown in Table 2.

[0401]

[0402] [Table 2]

[0403]

[0404] <Example of Z element - 1 (refer to Figure 2 )>

[0405] In Example - 1 of the X element, the compound Z(1 - 2) synthesized in Synthesis Example - 1 of Z was used to replace the compound X(1 - 2). Except for this, an organic electroluminescent element was fabricated using the same method as in Example - 1 of the X element and evaluated. The obtained measurement results are shown in Table 3.

[0406] <Example of Z element - 2>

[0407] In Example - 1 of the X element, the compound Z(1 - 13) synthesized in Synthesis Example - 2 of Z was used to replace the compound X(1 - 2). Except for this, an organic electroluminescent element was fabricated using the same method as in Example - 1 of the X element and evaluated. The obtained measurement results are shown in Table 3.

[0408] <Example of Z element - 3>

[0409] In Example - 1 of the X element, the compound Z(1 - 15) synthesized in Synthesis Example - 3 of Z was used to replace the compound X(1 - 2). Except for this, an organic electroluminescent element was fabricated using the same method as in Example - 1 of the X element and evaluated. The obtained measurement results are shown in Table 3.

[0410] <Reference Example of Z element - 1>

[0411] In Example - 1 of the Z element, the following compound (ETL - 1) described in Patent Document 1 (International Publication No. 2015 / 111848) was used to replace the compound Z(1 - 2). Except for this, an organic electroluminescent element was fabricated using the same method as in Example - 1 of the X element and evaluated.

[0412] The obtained measurement results are shown in Table 3.

[0413]

[0414] [Table 3]

[0415] compound Voltage Current efficiency Component lifespan Z-Element Example 1 1-2 96 107 150 Z-Element Example 2 1-13 98 115 105 Z-Element Example 3 1-15 95 106 140 Z-Component Reference Example-1 ETL-1 100 100 100

[0416] The triazine compound (1) according to one aspect of the present invention has a wide bandgap and a high triplet excitation energy level. Therefore, it is applicable not only to conventional fluorescent element applications but also to organic electroluminescent elements using phosphorescent elements and thermally activated delayed fluorescence (TADF).

Claims

1. A triazine compound, represented by formula Y(1), In formula Y(1), A represents an aryl group with 6 to 20 carbon atoms; B indicates: Choose one or more aryl groups with 6 to 20 carbon atoms selected from the group consisting of alkyl groups having 1 to 12 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cyano, diarylboroyl, and phosphine oxide, or Heteroaryl groups having 4 to 30 carbon atoms and containing oxygen or sulfur atoms; Ar 1 ~Ar 2 Each is expressed independently: Choose one or more aryl groups with 6 to 26 carbon atoms selected from the group consisting of alkyl groups with 1 to 12 carbon atoms, cycloalkyl groups with 3 to 20 carbon atoms, cyano groups, diarylboro groups, and phosphine oxide groups, or Pyridyl group optionally substituted with methyl or phenyl; n represents an integer from 0 to 1; L represents any group selected from formulas Y(2-1) to Y(2-5).

2. The triazine compound according to claim 1, wherein, A is phenyl, naphthyl, biphenyl, naphthylphenyl, phenylnaphthyl, binaphthyl, phenanthryl, anthraceneyl, terphenyl, or benzophenanthryl; B is selected from one or more substituted alkyl, cycloalkyl, cyano, diarylboryl and phosphine oxide groups consisting of alkyl with 1 to 12 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, cyano, diarylboryl and phosphine oxide, phenyl, naphthyl, biphenyl, naphthylphenyl, phenylnaphthyl, binaphthyl, phenanthryl, anthracene, terphenyl, benzophenanthryl, dibenzofuranyl, dibenzothiophene, or spiro[9H-fluorene-9,9'-[9H]xanthrene]-yl.

3. The triazine compound according to claim 1, wherein, A is a group selected from phenyl, biphenyl, naphthylphenyl, phenylnaphthyl, binaphthyl, or terphenyl. B can be optionally substituted with a cyano group, and can be phenyl, biphenyl, naphthylphenyl, phenylnaphthyl, or terphenyl.

4. The triazine compound according to claim 1, wherein, A is any group selected from formulas Y(A-1) to Y(A-10); B is any group selected from formulas Y(B-1) to Y(B-28).

5. The triazine compound according to any one of claims 1 to 4, wherein, Ar 1 ~Ar 2 Each of the following can be independently substituted with a cyano group: phenyl, 1-naphthyl, 2-naphthyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, biphenyl, naphthylphenyl, phenylnaphthyl, binaphthyl, anthraceneylphenyl, or phenylanthraylphenyl.

6. The triazine compound according to any one of claims 1 to 4, wherein, Ar 1 ~Ar 2 Each of these can be independently unsubstituted, phenyl, 1-naphthyl, 2-naphthyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, biphenyl, naphthylphenyl, phenylnaphthyl, binaphthyl, anthraceneylphenyl, or phenylanthraylphenyl.

7. A material for an organic electroluminescent element comprising any one of the triazine compounds according to claims 1 to 6.

8. An electron transport material for an organic electroluminescent element, comprising any one of the triazine compounds according to claims 1 to 6.

9. An organic electroluminescent element comprising the triazine compound according to any one of claims 1 to 6.

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