Organic electroluminescent element, display device, lighting device, and anthracene-based compound

Abstract

This invention relates to an organic electroluminescent element, a display device, a lighting device, and an anthracene compound, comprising a pair of electrodes and a light-emitting layer, wherein the pair of electrodes includes an anode and a cathode, the light-emitting layer is disposed between the pair of electrodes, and the light-emitting layer comprises an anthracene compound represented by the following formula (1) as the host material, and a polycyclic aromatic compound or polymer thereof represented by the following formula (2) as the dopant material (in formula (1), Ar...). c For aryl, etc., R c For hydrogen, etc., Ar 11 ~Ar 18 Any two of them are aryl, etc., and the others are hydrogen, etc., at least one hydrogen in formula (1) can be substituted by deuterium, etc., in formula (2), ring A, ring B and ring C are substituted aryl rings, etc., X 1 and X 2 For example, >O, >N-R (R is aryl, etc.).

Description

Technical Field

[0001] This invention relates to an organic electroluminescent element, a display device using the same, and a lighting device. Additionally, this invention relates to an anthracene compound that can be used as a luminescent material. Background Technology

[0002] Previously, display devices using electroluminescent elements were extensively studied due to their ability to achieve power savings or thinner designs. Furthermore, organic electroluminescence (OLED) elements (sometimes referred to as "organic EL elements") incorporating organic materials have been actively researched due to their ease of lightweighting and scaling. In particular, the development of organic materials with luminescent properties such as blue, one of the three primary colors of light, and the combination of various materials exhibiting optimal luminescent properties, whether polymeric or low-molecular-weight compounds, have been actively studied to date.

[0003] Organic EL devices have a structure comprising: a pair of electrodes including an anode and a cathode; and one or more layers containing an organic compound disposed between the pair of electrodes. The organic compound-containing layers include a light-emitting layer, a charge transport / injection layer for transporting or injecting charges such as holes and electrons, and various organic materials suitable for these layers are being developed.

[0004] Patent Document 1 describes the use of anthracene compounds as luminescent materials for organic electroluminescent elements. In addition, in recent years, polycyclic aromatic compounds with multiple aromatic rings condensed around boron or similar central atoms have been reported as materials for organic electroluminescent elements (Patent Document 2).

[0005] [Existing Technical Documents]

[0006] [Patent Literature]

[0007] [Patent Document 1] International Publication No. 2006 / 003842

[0008] [Patent Document 2] International Publication No. 2015 / 102118 Summary of the Invention

[0009] [The problem the invention aims to solve]

[0010] As described above, various materials have been developed for use in organic EL devices, but to increase the selection of materials for organic EL devices, it is desirable to develop a material containing compounds different from existing materials. The objective of this invention is to provide an organic EL device using a combination of novel materials. This invention aims to provide an organic EL device with high external quantum efficiency.

[0011] [Technical means to solve the problem]

[0012] The inventors conducted diligent research to solve the aforementioned problem, and as a result, discovered that by using a light-emitting layer containing a specific anthracene-based compound as the host material and a polycyclic aromatic compound with condensed aromatic rings as the dopant material, an excellent organic EL element can be obtained, thus completing the present invention. Specifically, the present invention provides an organic electroluminescent element and anthracene-based compound as described below.

[0013] <1> An organic electroluminescent element includes a pair of electrodes and a light-emitting layer, wherein the pair of electrodes includes an anode and a cathode, the light-emitting layer is disposed between the pair of electrodes, and the light-emitting layer includes an anthracene compound represented by the following formula (1) as the host material, and a polycyclic aromatic compound represented by the following formula (2) or a polymer having a plurality of polycyclic aromatic compounds represented by the following formula (2) as the dopant material.

[0014] [Chemistry 1]

[0015]

[0016] In equation (1),

[0017] Ar c It is a substituted aryl group or a substituted heteroaryl group.

[0018] R c It is hydrogen, alkyl or cycloalkyl,

[0019] Ar 11 Ar 12 Ar 13 Ar 14 Ar 15 Ar 16 Ar 17 and Ar 18 Each of the following can be independently hydrogen, a substituted aryl group, a substituted heteroaryl group, a substituted diarylamino group, a substituted diheteroarylamino group, a substituted arylheteroarylamino group, a substituted alkyl group, a substituted cycloalkyl group, a substituted alkenyl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, or a substituted silyl group.

[0020] At least one hydrogen atom in the compound represented by formula (1) may be substituted by halogen, cyano or deuterium.

[0021] In equation (2),

[0022] Rings A, B, and C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings can be substituted.

[0023] X1 and X 2 Each of the following can be independently represented as >O, >NR, >C(-R)2, >S, or >Se, wherein the R in >NR is a substituted aryl, substituted heteroaryl, substituted alkyl, or substituted cycloalkyl, and the R in >C(-R)2 is hydrogen, a substituted aryl, a substituted alkyl, or a substituted cycloalkyl. Furthermore, the R in >NR and / or the R in >C(-R)2 can be bonded to the A, B, and / or C rings via a linking group or a single bond.

[0024] At least one of the aryl ring and heteroaryl ring in the compound represented by formula (2) or its polymer may be condensed from at least one cycloalkane, wherein at least one hydrogen atom in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-.

[0025] At least one hydrogen atom in the compound or structure represented by formula (2) may be replaced by deuterium, cyano or halogen.

[0026] <2> According to the organic electroluminescent element described in <1>, the polycyclic aromatic compound represented by formula (2) or a polymer of a polycyclic aromatic compound having a plurality of structures represented by formula (2) is a polycyclic aromatic compound represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f) or a polymer of a polycyclic aromatic compound having a plurality of structures represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f).

[0027] [Chemistry 2]

[0028]

[0029] In equations (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f),

[0030] R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 and R 11Each of the following is independently hydrogen, aryl, heteroaryl, diarylamino, diheterarylamino, arylheterarylamino, diarylboryl (the two aryl groups may be linked by a single bond or a linker group), alkyl, cycloalkyl, alkoxy, aryloxy, or a substituted silyl group, wherein at least one hydrogen atom may be substituted by an aryl, heteroaryl, alkyl, cycloalkyl, or a substituted silyl group, R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 and R 11 The adjacent groups in the ring may bond to each other and together with ring a, ring b, or ring c to form an aryl ring or a heteroaryl ring. At least one hydrogen in the formed ring may be substituted by an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or a substituted silyl group. At least one hydrogen in these rings may be substituted by an aryl, heteroaryl, alkyl, cycloalkyl, or a substituted silyl group.

[0031] X X Each of the following can be independently >O, >S, >NR, or >C(-R)2, wherein the R in >NR is a substituted aryl, a substituted heteroaryl, a substituted alkyl, or a substituted cycloalkyl, and the R in >C(-R)2 can be independently hydrogen, an aryl group substituted by an alkyl or cycloalkyl group, a heteroaryl group substituted by an alkyl or cycloalkyl group, an alkyl, or a cycloalkyl.

[0032] X 1 and X 2 Each is independently >O, >NR, >C(-R)2, >S, or >Se, wherein R in >NR is an aryl group of 6-12 carbons that can be substituted with an alkyl group of 1-6 carbons or a cycloalkyl group of 3-14 carbons, a heteroaryl group of 2-15 carbons that can be substituted with an alkyl group of 1-6 carbons or a cycloalkyl group of 3-14 carbons, or an alkyl group of 1-6 carbons or a cycloalkyl group of 3-14 carbons, and R in >C(-R)2 is hydrogen, which can be substituted with an alkyl group of 1-6 carbons or a cycloalkyl group of 3-14 carbons. The alkyl group or cycloalkyl group with 3 to 14 carbon atoms substituted with an aryl group with 6 to 12 carbon atoms, an alkyl group with 1 to 6 carbon atoms, or a cycloalkyl group with 3 to 14 carbon atoms, wherein the R group of the >NR group and / or the R group of the >C(-R)2 group can be bonded to the a ring, b ring, and / or c ring via -O-, -S-, -C(-R)2- or a single bond, and the R group of the -C(-R)2- group is independently an alkyl group with 1 to 6 carbon atoms or a cycloalkyl group with 3 to 14 carbon atoms.

[0033] At least one of the aryl and heteroaryl rings in the compounds or polymers represented by formulas (2-a), (2-b), (2-c), (2-d), (2-e), or (2-f) may be condensed from at least one cycloalkane, wherein at least one hydrogen atom in the cycloalkane may be substituted, and at least one -CH2- atom in the cycloalkane may be substituted with -O-.

[0034] In the compounds or structures represented by formulas (2-a), (2-b), (2-c), (2-d), (2-e), or (2-f), at least one hydrogen atom may be substituted by a deuterium, cyano, or halogen.

[0035] In the case of a polymer, it is a dimer or trimer having two or three structures represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f).

[0036] <3> The organic electroluminescent element according to <2>, wherein the compound represented by formula (2) is a polycyclic aromatic compound represented by formula (2-a) or formula (2-b) or a polymer of a plurality of polycyclic aromatic compounds having the structure represented by formula (2-a) or formula (2-b).

[0037] <4> According to <3>, the organic electroluminescent element, wherein the compound represented by formula (2) is any one of the compounds represented by the following formulas,

[0038] [Chemistry 3]

[0039]

[0040] [Chemistry 4]

[0041]

[0042] [Chemistry 5]

[0043]

[0044] In the formula, Me is methyl, tBu is tert-butyl, tAm is tert-pentyl, and D is deuterium.

[0045] <5> An organic electroluminescent element according to any one of <1> to <4>, wherein in formula (1),

[0046] Ar 11 Ar 12 Ar 13 Ar 14 Ar 15 Ar 16 Ar 17 and Ar 18Any two of them are substituted aryl or substituted heteroaryl, and the other six are hydrogen, substituted alkyl, substituted cycloalkyl, substituted alkenyl or substituted alkoxy.

[0047] <6> According to the organic electroluminescent element described in <5>, wherein the anthracene compound represented by formula (1) is an anthracene compound represented by formula (1A), formula (1B), formula (1C), formula (1D) or formula (1E) below.

[0048] [Chemistry 6]

[0049]

[0050] In equation (1A), equation (1B), equation (1C), equation (1D), or equation (1E),

[0051] Ar c '、Ar 11 '、Ar 12 '、Ar 13 '、Ar 14 '、Ar 15 '、Ar 17 'and Ar 18 'Each of the following is independently a phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthryl, fluorenyl, benzo[2]fluorenyl, The group may be phenyl, triphenyl, pyrene, or a group represented by formula (A), wherein at least one hydrogen atom in these groups may be derived from phenyl, biphenyl, triphenyl, tetraphenyl, naphthyl, phenanthryl, fluorene, benzo[a]fluorene, or phenyl[b]fluorene. The fluorene group, triphenylene group, pyrene group, or group represented by formula (A) is substituted. Here, when both hydrogens of the methylene group in the fluorene group and the benzo[a]fluorene group are substituted with phenyl groups, these phenyl groups can be bonded to each other by single bonds.

[0052] In the unbonded Ar c '、Ar 11 '、Ar 12 '、Ar 13 '、Ar 14 '、Ar 15 '、Ar 17 'or Ar 18 The carbon atoms on the anthracene ring can be bonded with methyl or tert-butyl groups to replace hydrogen.

[0053] At least one hydrogen atom in the compound represented by formula (1A), formula (1B), formula (1C), formula (1D), or formula (1E) may be substituted with a halogen, a cyano group, or a deuterium.

[0054] The base represented by formula (A) is obtained by removing a hydrogen atom from any position in formula (A), where * indicates the position.

[0055] In equation (A), Y is -O-, -S-, or >NR. 39 R 21 ~R 28 Each of the following is independently hydrogen, a substituted alkyl group, a substituted cycloalkyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, a substituted amino group, a halogen, a hydroxyl group, or a cyano group, R. 21 ~R 28 The adjacent groups can bond to each other to form a hydrocarbon ring, aryl ring, or heteroaryl ring. At least one hydrogen atom in the formed hydrocarbon ring, aryl ring, or heteroaryl ring can be substituted by a substituted alkyl group, a substituted cycloalkyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, a substituted amino group, a halogen group, a hydroxyl group, or a cyano group. 39 It is hydrogen or a substituted aryl group.

[0056] <7> The organic electroluminescent element according to <6>, wherein

[0057] The basis represented by equation (A) is any one of the bases represented by equations (A-1) to (A-14).

[0058] The bases represented by formulas (A-1) to (A-14) are bases obtained by removing a hydrogen atom from any position in each of formulas (A-1) to (A-14), where * indicates the position.

[0059] In equations (A-1) to (A-14), Y is -O-, -S-, or >NR. 39 R 39 It is hydrogen or aryl, and at least one hydrogen in the group represented by formula (A-1) to (A-14) may be substituted by alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxyl or cyano.

[0060] [Chemistry 7]

[0061]

[0062] <8> The organic electroluminescent element according to <6> or <7>, wherein

[0063] Ar c '、Ar11 '、Ar 12 '、Ar 13 '、Ar 14 '、Ar 15 '、Ar 17 'and Ar 18 Each group is independently represented by a group consisting of phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, or any of the groups (A-1) to (A-4), wherein at least one hydrogen atom in these groups may be substituted by a group consisting of phenyl, biphenyl, naphthyl, phenanthryl, fluorenyl, or any of the groups (A-1) to (A-4).

[0064] At least one hydrogen atom in the compound represented by formula (1A), formula (1B), formula (1C), formula (1D) or formula (1E) may be substituted with halogen, cyano or deuterium.

[0065] <9> According to <5>, the organic electroluminescent element, wherein Ar 14 Ar 15 Ar is a substituted aryl group or a substituted heteroaryl group. 11 Ar 12 Ar 13 Ar 16 Ar 17 and Ar 18 Both are hydrogen.

[0066] <10> The organic electroluminescent element according to <9>, wherein Ar is selected c Ar 14 and Ar 15 At least one of the groups is a base containing anthracene rings.

[0067] <11> The organic electroluminescent element according to <9>, wherein Ar is selected c Ar 14 and Ar 15 The base represented by at least one inclusion expression (A') in the group formed.

[0068] [Chemistry 8]

[0069]

[0070] In formula (A'), R 21 ~R 28 Each of the following is independently hydrogen, a substituted alkyl group, a substituted cycloalkyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, a substituted amino group, a halogen, a hydroxyl group, or a cyano group, R. 21~R 28 The adjacent groups can bond with each other to form a hydrocarbon ring, aryl ring, or heteroaryl ring. At least one hydrogen in the formed hydrocarbon ring, aryl ring, or heteroaryl ring can be substituted by a substituted alkyl group, a substituted cycloalkyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, a substituted amino group, a halogen group, a hydroxyl group, or a cyano group.

[0071] <12> According to <9>, in the organic electroluminescent element, at least one hydrogen in the compound represented by formula (1) may be replaced by deuterium.

[0072] <13> An organic electroluminescent element according to any one of <1> to <12> has an electron transport layer and / or an electron injection layer disposed between the cathode and the light-emitting layer, wherein at least one layer of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzo[a]fluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, aryl nitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, hydroxyquinoline metal complexes, thiazole derivatives, benzo[a]thiazole derivatives, thiophene derivatives, and azoline derivatives.

[0073] <14> The organic electroluminescent element according to <13>, wherein the electron transport layer and / or electron injection layer further comprises at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals.

[0074] <15> A display device comprising an organic electroluminescent element according to any one of <1> to <14>.

[0075] <16> A lighting device comprising an organic electroluminescent element according to any one of <1> to <14>.

[0076] <17> An anthracene compound, represented by the following formula (1):

[0077] [Chemistry 9]

[0078]

[0079] In equation (1),

[0080] Arc It is a substituted aryl group or a substituted heteroaryl group.

[0081] R c It is hydrogen, alkyl or cycloalkyl,

[0082] Ar 11 Ar 12 Ar 13 Ar 14 Ar 15 Ar 16 Ar 17 and Ar 18 Each of the following can be independently hydrogen, a substituted aryl group, a substituted heteroaryl group, a substituted diarylamino group, a substituted diheteroarylamino group, a substituted arylheteroarylamino group, a substituted alkyl group, a substituted cycloalkyl group, a substituted alkenyl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, or a substituted silyl group.

[0083] At least one hydrogen atom in the compound represented by formula (1) may be substituted by halogen, cyano or deuterium.

[0084] <18> The anthracene compounds according to <17> are represented by the following formula (1Aa):

[0085] [Chemistry 10]

[0086]

[0087]

[0088] In equation (1Aa), Ar c '、Ar 14 'and Ar 15 'Each of the following groups is independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, benzo[2]fluorenyl, The group consisting of a phenyl group, a triphenylene group, a pyrene group, or a group represented by any of the formulas (A-1) to (A-14), wherein at least one hydrogen atom in these groups may be represented by a phenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, a naphthyl group, a phenanthryl group, a fluorene group, a benzo[a]fluorene group, or a group represented by a phenyl group, a triphenylene group, a ... Substitution of the methyl group, triphenylene, pyrene, or any of the methyl groups represented by formulas (A-1) to (A-14), wherein, when the hydrogen atoms of the methylene group in both the fluorene group and the benzo[a]fluorene group are substituted by phenyl groups, these phenyl groups can be bonded to each other by single bonds, and in the unbonded Ar... c '、Ar 14 'or Ar 15 The carbon atoms on the anthracene ring can be bonded with methyl or tert-butyl groups to replace hydrogen.

[0089] At least one hydrogen atom in the compound represented by formula (1Aa) may be substituted by a halogen, a cyano group, or a deuterium.

[0090] The bases represented by formulas (A-1) to (A-14) are bases obtained by removing a hydrogen atom from any position in each of formulas (A-1) to (A-14), where * indicates the position.

[0091] In equations (A-1) to (A-14), Y is -O-, -S-, or >NR. 39 R 39 The hydrogen group is hydrogen or aryl, and at least one hydrogen group in the groups represented by formulas (A-1) to (A-14) may be substituted by alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxyl, or cyano.

[0092] In the compound represented by formula (1Aa), at least one hydrogen atom may be substituted by a halogen or a cyano group, and at least one hydrogen atom may be substituted by a deuterium group.

[0093] <19> According to <18>, the anthracene compounds, wherein Ar c '、Ar 14 'and Ar 15 Each group is independently represented by a group consisting of phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, or any of the groups (A-1) to (A-4), wherein at least one hydrogen atom of these groups may be substituted by a group consisting of phenyl, naphthyl, phenanthryl, fluorenyl, or any of the groups (A-1) to (A-4).

[0094] <20> According to <18> or <19>, in the anthracene compound, at least the hydrogen bonded to the 10 position of the anthracene ring in formula (1Aa) is replaced with deuterium.

[0095] <21> According to <18>, the anthracene compounds are represented by any of the following formulas:

[0096] [Chemistry 11]

[0097]

[0098] [Chemistry 12]

[0099]

[0100] [Chemistry 13]

[0101]

[0102] [Chemistry 14]

[0103]

[0104] (In the formula, D represents deuterium).

[0105] <22> According to <17>, the anthracene compounds are represented by any of the following formulas:

[0106] [Chemistry 15]

[0107]

[0108] [Chemistry 16]

[0109]

[0110] [Chemistry 17]

[0111]

[0112] [Chemistry 18]

[0113]

[0114] [Chemistry 19]

[0115]

[0116] [Chemistry 20]

[0117]

[0118] [Chemistry 21]

[0119]

[0120] (In the formula, D represents deuterium).

[0121] <23> According to <17>, anthracene compounds are represented by any of the following formulas:

[0122] [Chemistry 22]

[0123]

[0124] [Chemistry 23]

[0125]

[0126] [Chemistry 24]

[0127]

[0128] [Chemistry 25]

[0129]

[0130] <24> The anthracene compounds according to <17> are represented by any of the following formulas:

[0131] [Chemistry 26]

[0132]

[0133] [Chemistry 27]

[0134]

[0135] [Chemistry 28]

[0136]

[0137] [Chemistry 29]

[0138]

[0139] (In the formula, D represents deuterium).

[0140] <25> The anthracene compounds according to <17> are represented by any of the following formulas:

[0141] [Chemistry 30]

[0142]

[0143] [Chemistry 31]

[0144]

[0145] (In the formula, D represents deuterium).

[0146] <26> According to <17>, the anthracene compounds are represented by any of the following formulas:

[0147] [Chemistry 32]

[0148]

[0149] (In the formula, Me represents methyl, tBu represents tert-butyl, and CyHex represents cyclohexyl).

[0150] <27> The anthracene compounds according to <17> are represented by any of the following formulas:

[0151] [Chemistry 33]

[0152]

[0153] [Chemistry 34]

[0154]

[0155] (In the formula, D represents deuterium).

[0156] [The effects of the invention]

[0157] This invention provides an organic EL element using a combination of novel materials. The organic EL element of this invention exhibits high external quantum efficiency and is capable of emitting light at low voltages. Furthermore, this invention provides an anthracene-based compound that can be used to manufacture the organic EL element. Attached Figure Description

[0158] Figure 1 This is a schematic cross-sectional view illustrating an example of the organic EL element of the present invention.

[0159] [Explanation of Symbols]

[0160] 100: Organic electroluminescent element

[0161] 101: Substrate

[0162] 102: Anode

[0163] 103: Hole Injection Layer

[0164] 104: Hole Transport Layer

[0165] 105: Emissive layer

[0166] 106: Electron Transport Layer

[0167] 107: Electron Injection Layer

[0168] 108: Cathode Detailed Implementation

[0169] The present invention will now be described in detail. The descriptions of the constituent elements described below are sometimes based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. Furthermore, in this specification, the numerical range indicated by “~” refers to the range including the values ​​described before and after “~” as both the lower and upper limits. Additionally, in this specification, “hydrogen” in the description of the structural formula refers to “hydrogen atom (H)”.

[0170] In this specification, the number of carbon atoms is sometimes used to represent chemical structures or substituents. However, when a substituent is substituted in a chemical structure, or when a substituent is further substituted on a substituent, the number of carbon atoms refers to the individual carbon atom of the chemical structure or substituent, and not the total number of carbon atoms of the chemical structure and the substituent, or the total number of carbon atoms of the substituents. For example, "substituent B with carbon atom number X replaced by substituent A with carbon atom number X" means that "substituent A with carbon atom number X" is substituted on "substituent B with carbon atom number Y," and the number of carbon atoms Y is not the total number of carbon atoms of substituent A and substituent B. Similarly, "substituent B with carbon atom number Y replaced by substituent A" means that "substituent A (without a specified number of carbon atoms) is substituted on "substituent B with carbon atom number Y," and the number of carbon atoms Y is not the total number of carbon atoms of substituent A and substituent B.

[0171] <<Organic Electroluminescent Devices>>

[0172] The organic electroluminescent element of the present invention includes: a pair of electrodes, comprising an anode and a cathode; and a light-emitting layer disposed between the pair of electrodes. Figure 1 This is a schematic cross-sectional view illustrating an example of the organic EL element of the present invention.

[0173] Figure 1 The organic EL element 100 shown includes: a substrate 101, an anode 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode 102, a hole transport layer 104 disposed on the hole injection layer 103, a light-emitting layer 105 disposed on the hole transport layer 104, an electron transport layer 106 disposed on the light-emitting layer 105, an electron injection layer 107 disposed on the electron transport layer 106, and a cathode 108 disposed on the electron injection layer 107.

[0174] Furthermore, the organic EL element 100 can also be fabricated in reverse order to form a structure such as the following, which includes: a substrate 101, a cathode 108 disposed on the substrate 101, an electron injection layer 107 disposed on the cathode 108, an electron transport layer 106 disposed on the electron injection layer 107, a light-emitting layer 105 disposed on the electron transport layer 106, a hole transport layer 104 disposed on the light-emitting layer 105, a hole injection layer 103 disposed on the hole transport layer 104, and an anode 102 disposed on the hole injection layer 103.

[0175] Not all of the aforementioned layers are necessary. The smallest structural unit can be defined as including an anode 102, a light-emitting layer 105, and a cathode 108. The hole injection layer 103, hole transport layer 104, electron transport layer 106, and electron injection layer 107 are arbitrarily arranged layers. Furthermore, each layer may consist of a single layer or multiple layers.

[0176] In addition to the aforementioned structure of "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", the morphology of the layers constituting an organic EL device can also be "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting ...". The structural forms are: “substrate / anode / electron transport layer / electron injection layer / cathode”, “substrate / anode / hole transport layer / electron injection layer / cathode”, “substrate / anode / hole transport layer / electron transport layer / electron injection layer / cathode”, “substrate / anode / hole transport layer / electron transport layer / cathode”, “substrate / anode / hole injection layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / electron transport layer / cathode”, “substrate / anode / electron transport layer / cathode”, “substrate / anode / electron transport layer / cathode”.

[0177] 1. The light-emitting layer of an organic electroluminescent element

[0178] The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 with electrons injected from the cathode 108 between electrodes to which an electric field is applied. As the material for forming the light-emitting layer 105, any compound that emits light when excited by the recombination of holes and electrons (a luminescent compound) is acceptable, and preferably a compound that can form a stable thin film shape and exhibits strong luminescence (fluorescence) efficiency in the solid state.

[0179] The light-emitting mechanisms of organic EL devices mainly include fluorescence emission, which uses light emitted from the excited singlet state, and phosphorescence emission, which uses light emitted from the excited triplet state. Typical fluorescent light-emitting materials have low exciton utilization efficiency, with a maximum of 25%. However, by utilizing the phenomenon of generating singlet excitons from multiple triplet excitons (triplet-triplet fusion (TTF), up to 40%–62.5% of the energy can be used for light emission.

[0180] There are two scenarios for the generation of singlet excitons from triplet excitons: occurring on the host material molecules and occurring on the dopant material molecules. Preferably, the triplet energy level of the dopant material is higher than that of the host material. If this triplet energy level relationship is satisfied, triplet excitons generated on the host material will not transfer to the dopant material, which has a higher triplet energy. Alternatively, triplet excitons generated on the dopant material molecules rapidly transfer energy to the host material molecules. That is, triplet excitons in the host material do not transfer to the dopant material; instead, triplet excitons collide efficiently with each other in the host material, generating singlet excitons. Furthermore, when the singlet energy level of the dopant material is lower than that of the host material, singlet excitons generated by the TTF phenomenon rapidly transfer energy from the host material to the dopant material, contributing to the fluorescence of the dopant material. Additionally, this energy transfer from the host to the dopant is a Foerster-type energy transfer. Generally speaking, it is known that in organic EL devices, the overlap integral between the fluorescence spectrum of the host and the absorption spectrum of the dopant is large. When the host and the dopant are close to each other and achieve appropriate orientation, high-efficiency Fernandes-type energy transfer will be induced.

[0181] By utilizing the anthracene compound as the host material represented by formula (1) of the present invention and the boron-containing polycyclic aromatic compound as the dopant material represented by formula (2), it is possible to design materials and devices that satisfy the appropriate energy level relationship between the host and the dopant and the conditions for inducing highly efficient Fils-type energy transfer. As a result, TTF phenomenon can be efficiently generated in the light-emitting layer of the present invention, and good device characteristics can be imparted.

[0182] The light-emitting layer of the organic electroluminescent element of the present invention comprises an anthracene compound represented by formula (1) as the host material, and a polycyclic aromatic compound represented by formula (2) or a polymer of a polycyclic aromatic compound having a structure represented by multiple formulas (2) as the dopant material.

[0183] 1-1-1. Anthracene compounds

[0184] The anthracene compounds contained in the light-emitting layer of the organic EL element of the present invention are compounds represented by the following formula (1).

[0185] [Chemistry 35]

[0186]

[0187] In equation (1), Ar c R is a substituted aryl group or a substituted heteroaryl group. c It is hydrogen, alkyl or cycloalkyl, Ar 11 Ar 12 Ar13 Ar 14 Ar 15 Ar 16 Ar 17 and Ar 18 Each of the following is independently hydrogen, a substituted aryl, a substituted heteroaryl, a substituted diarylamino, a substituted diheteroarylamino, a substituted arylheteroarylamino, a substituted alkyl, a substituted cycloalkyl, a substituted alkenyl, a substituted alkoxy, a substituted aryloxy, a substituted arylthio, or a substituted silyl, wherein at least one hydrogen atom in the compound represented by formula (1) may be substituted with a halogen, a cyano, or a deuterium.

[0188] The "aryl" in formula (1) can be aryl with 6 to 30 carbons, preferably aryl with 6 to 16 carbons, more preferably aryl with 6 to 12 carbons, and particularly preferably aryl with 6 to 10 carbons.

[0189] Specific examples of "aryl" groups include: phenyl (monocyclic); biphenyl (bicyclic); naphthyl (condensed bicyclic); terphenyl (m-terphenyl, o-terphenyl, p-terphenyl) (tricyclic); anthracene, acenaphthene, fluorenyl, phenatenyl, phenanthreneyl (condensed tricyclic); triphenylene, pyrene, tetraphenyl, benzo[a]fluorenyl (condensed tetracyclic); and perylene, pentaphenyl, etc. (condensed pentacyclic). Furthermore, in this specification, when "fluorenyl" is mentioned, it means that one or both hydrogen atoms of the methylene group of the fluorenyl group are substituted with a methyl group. Similarly, when "benzo[a]fluorenyl" is mentioned, it means that one or both hydrogen atoms of the methylene group of the benzo[a]fluorenyl group are substituted with a methyl group.

[0190] The "heteroaryl" in formula (1) can be categorized as a heteroaryl group having 2 to 30 carbon atoms, preferably a heteroaryl group having 2 to 25 carbon atoms, more preferably a heteroaryl group having 2 to 20 carbon atoms, and even more preferably a heteroaryl group having 2 to 15 carbon atoms, and particularly preferably a heteroaryl group having 2 to 10 carbon atoms. Furthermore, heterocyclic rings containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-forming atoms, in addition to carbon atoms, can be cited as examples.

[0191] Specific examples of "heteroaryl" groups include: pyrrole, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazole, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, indole, isoindole, 1H-indazole, benzimidazole, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, and isoquinolinyl. , ...

[0192] As for the aryl and heteroaryl groups in "substitutable diarylamino", "substitutable diheteroarylamino", and "substitutable arylheteroarylamino" in formula (1), the groups described above as "aryl" and "heteroaryl" can be referred to.

[0193] Specifically, examples include: diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, etc.

[0194] The "alkyl" in formula (1) and "substituted alkyl" can be either straight-chain or branched, for example, straight-chain alkyl with 1 to 24 carbon atoms or branched alkyl with 3 to 24 carbon atoms. Preferably, it is an alkyl with 1 to 18 carbon atoms (branched alkyl with 3 to 18 carbon atoms), more preferably an alkyl with 1 to 12 carbon atoms (branched alkyl with 3 to 12 carbon atoms), and even more preferably an alkyl with 1 to 6 carbon atoms (branched alkyl with 3 to 6 carbon atoms), and particularly preferably an alkyl with 1 to 4 carbon atoms (branched alkyl with 3 to 4 carbon atoms).

[0195] Specific examples of "alkyl groups" include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc.

[0196] As "cycloalkyl" and "substituted cycloalkyl" in formula (1), cycloalkyl with 3 to 24 carbon atoms can be listed, preferably cycloalkyl with 3 to 20 carbon atoms, more preferably cycloalkyl with 3 to 16 carbon atoms, and even more preferably cycloalkyl with 3 to 14 carbon atoms, and even more preferably cycloalkyl with 5 to 10 carbon atoms, particularly preferably cycloalkyl with 5 to 8 carbon atoms, and most preferably cycloalkyl with 5 to 6 carbon atoms.

[0197] Specific examples of cycloalkyl groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and their alkyl (especially methyl) substituted derivatives having 1 to 4 carbon atoms, or norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diadamantyl, decahydronaphthyl, decahydroazyl, etc.

[0198] The "alkenyl" in formula (1) that is "substitutable alkenyl" can be exemplified by straight-chain alkenyl groups having 2 to 24 carbons or branched alkenyl groups having 4 to 24 carbons. Alkenyl groups having 2 to 18 carbons are preferred, alkenyl groups having 2 to 12 carbons are more preferred, alkenyl groups having 2 to 6 carbons are even more preferred, and alkenyl groups having 2 to 4 carbons are particularly preferred.

[0199] Specific examples of "alkenyl" include vinyl, allyl, butadienyl, etc.

[0200] The "alkoxy group" in formula (1) that is "substitutable alkoxy group" can be, for example, a straight-chain alkoxy group having 1 to 24 carbon atoms or a branched-chain alkoxy group having 3 to 24 carbon atoms. Preferably, it is an alkoxy group having 1 to 18 carbon atoms (a branched-chain alkoxy group having 3 to 18 carbon atoms), more preferably an alkoxy group having 1 to 12 carbon atoms (a branched-chain alkoxy group having 3 to 12 carbon atoms), and even more preferably an alkoxy group having 1 to 6 carbon atoms (a branched-chain alkoxy group having 3 to 6 carbon atoms), and particularly preferably an alkoxy group having 1 to 4 carbon atoms (a branched-chain alkoxy group having 3 to 4 carbon atoms).

[0201] Specific examples of "alkoxy groups" include: methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentoxy, hexoxy, heptoxy, octoxy, etc.

[0202] As “aryloxy group” in formula (1) is a group in which the hydrogen of the -OH group is replaced by an aryl group, which may refer to the group described as “aryl”.

[0203] As in "substitutable arylthio" in formula (1), "arylthio" is a group in which the hydrogen of the -SH group is replaced by an aryl group, and the aryl group can be referenced as the Ar 4And the "aryl" in X is the base.

[0204] As "substitutable silyl group" in formula (1), trialkylsilyl groups can be listed. As "trialkylsilyl group", groups in which the three hydrogens of the silyl group are each independently substituted by an alkyl group can be listed, wherein the alkyl group can be referred to as the Ar. 4 The "alkyl" in X refers to the group. For substitution, the preferred alkyl group is an alkyl group having 1 to 4 carbon atoms, specifically including: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, cyclobutyl, etc.

[0205] Specific examples of "trialkylsilyl" include: trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, tritert-butylsilyl, ethyl dimethylsilyl, propyl dimethylsilyl, isopropyl dimethylsilyl, butyl dimethylsilyl, sec-butyl dimethylsilyl, tert-butyl dimethylsilyl, methyl diethylsilyl, propyl diethylsilyl, isopropyl diethylsilyl, butyl diethylsilyl, sec-butyl diethylsilyl, tert-butyl diethylsilyl, methyl dipropylsilyl, ethyl dipropylsilyl, butyl dipropylsilyl, sec-butyl dipropylsilyl, tert-butyl diisopropylsilyl, methyl diisopropylsilyl, ethyl diisopropylsilyl, butyl diisopropylsilyl, sec-butyl diisopropylsilyl, tert-butyl diisopropylsilyl, etc.

[0206] Regarding Ar in equation (1) c Ar 11 Ar 12 Ar 13 Ar 14 Ar 15 Ar 16 Ar 17 and Ar 18 As a substituent when "substitutable", alkyl, aryl, or heteroaryl groups can be listed. The groups described above as "alkyl", "aryl", or "heteroaryl" can be used as examples. The number of substituents can be any number up to the maximum number of substitutable groups, preferably 0 to 3, more preferably 0 to 2, and even more preferably 0 to 1. When multiple substituents are present, the multiple substituents can be bonded to each other. For example, when the hydrogens of the methylene groups in fluorene and benzo[a]fluorene are both replaced by phenyl groups, these phenyl groups can be bonded to each other by single bonds.

[0207] As a preferred example of a "substitutable aryl", the groups represented by any of the following formulas (1-X1) to (1-X7) can be listed.

[0208] [Chemistry 36]

[0209]

[0210] In equations (1-X1) to (1-X7), * indicates the location of the bond.

[0211] In equations (1-X1) to (1-X3), Ar 21 Ar 22 and Ar 23 Each of the following is independently hydrogen, phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthryl, fluorenyl, benzo[a]fluorenyl, The radical, triphenylene, pyrene, anthracene or the radical represented by formula (A) described later.

[0212] In equations (1-X4) to (1-X7), Ar 24 Ar 25 Ar 26 Ar 27 and Ar 28 Each of the following is independently hydrogen, phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, and [other compounds]. The radical, triphenylene, pyrene, anthracene or the radical represented by formula (A) described later.

[0213] In equations (1-X1) to (1-X7), in Ar 21 Ar 22 Ar 23 Ar 24 Ar 25 Ar 26 Ar 27 and Ar 28 In the case of anthraceneyl, at least one hydrogen atom in the anthraceneyl group may be derived from phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthryl, fluorenyl, benzo[a]fluorenyl, etc. Substitution with alkyl, triphenylene, pyrene or the alkyl group represented by formula (A) described later.

[0214] In addition, any one or more hydrogen atoms in each of the groups represented by formulas (1-X1) to (1-X7) may be replaced by alkyl groups having 1 to 6 carbon atoms (preferably methyl or tert-butyl).

[0215] Furthermore, as preferred examples of "substituted aryl groups", those selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorene, etc., can be listed. A terphenyl group (particularly meta-terphenyl-5'-yl) substituted with one or more of the groups consisting of methyl, triphenylene, pyrene, and methyl groups represented by formula (A) described below.

[0216] As "substitutable heteroaryl", any of the bases represented by formulas (A), (B), (C), (D), and (E) described later can also be listed.

[0217] Furthermore, as a "substitutable aryl" or "substitutable heteroaryl", a preferred example is a group in which an aryl or heteroaryl group is bonded to a carbon atom adjacent to the carbon atom at the bonding position of the group. Specifically, this refers to the group represented by the following formula (1-XB), and the group represented by formula (1-X6) is an example of the group represented by formula (1-XB).

[0218] [Chemistry 37]

[0219]

[0220] In equation (1-XB), Ar B1 Ar is an aryl group that may have substituents or a heteroaryl group that may have substituents. B1 The benzene ring undergoing bonding can condense with other aryl or heteroaryl rings to form a fused ring, Ar B2 Ar is an aryl group that may have substituents or a heteroaryl group that may have substituents. B2 It forms an atomic bond with the benzene ring or any ring in the fused ring, where n is an integer from 0 to 2. When n is 2, multiple Ar atoms... B2 They can be the same or different. The dashed line represents the skeleton of the aryl ring or the heteroaryl ring that forms a fused ring with the benzene ring, and * indicates the bonding position of the group represented by formula (1-XB). In formula (1-XB), the substituent when "may have substituents" is aryl or heteroaryl. Formula (1-XB) preferably has at least one fused ring. For example, Ar is preferred. B1 The benzene ring undergoing bonding condenses with other aryl or heteroaryl rings to form a fused ring, or Ar... B1 or more than one Ar B2 It contains a fused ring. Examples of fused rings include naphthalene rings, phenanthrene rings, triphenylene rings, and dibenzofuran rings. Formula (1-XB) preferably has at least one fused ring, and n is 1.

[0221] For example, Ar 14 Ar 15 Ar is a substituted aryl group or a substituted heteroaryl group. 11 Ar 12 Ar 13 Ar 16 Ar 17 and Ar 18 All are hydrogen, and are selected from Ar c Ar 14 and Ar 15Anthracene compounds comprising at least one group of compounds containing a group represented by formula (1-XB) are among the preferred forms. In this case, R c Hydrogen is preferred.

[0222] As specific examples, the compounds represented by the following formula numbers in Table 1 can be listed: (1-124), (1-4133), (1-148), (1-150), (1-136), (1-4155), (1-3268), (1-4114), (1-4121), (1-4119), (1-4120), (1-4107), (1-4317), (1-4327), (1-3991), (1-2984), (1-3452), (1-2883), (1-4205), (1-4232), (1-4219), (1-4254), (1-4263), (1-4271), (1-2995), (1-3005), (1-3020), (1-4204), (1-419) 8), (1-4280), (1-3821), (1-3078), (1-4209), (1-4093), (1-4092), (1-2977), (1-4036), (1-4335), (1-4347), (1-4354), (1-3751), (1-4368), (1-4372), (1-4334), (1- 4330), (1-4106), (1-3830), (1-3839), (1-4381), (1-4390), (1-3837), (1-3854), (1-4091), (1-3859), (1-4701), (1-4688), (1-4715), (1-4565), (1-4736), (1-4112).

[0223] The anthracene compounds represented by formula (1) are also preferably substituents containing an anthracene ring as “substitutable aryl” or “substitutable heteroaryl”.

[0224] For example, when Ar 14 Ar 15 It is a substituted aryl group or a substituted heteroaryl group, and Ar 11 Ar 12 Ar 13 Ar 16 Ar 17 and Ar 18 When both are hydrogen, it is preferable to select Ar. c Ar 14 and Ar 15 At least one of the groups consists of a group containing an anthracene ring. In this case, R cHydrogen is preferred.

[0225] Examples of groups comprising an anthracene ring include: anthracene groups that may have substituents; any of formulas (1-X1) to (1-X7), wherein Ar in the formula... 21 Ar 22 Ar 23 Ar 24 Ar 25 Ar 26 、or Ar 27 and / or Ar 28 A group that is an anthracene group that may have substituents; and a group represented by formula (A) described later, and chosen from R. 21 ~R 28 and R 39 Any one or two of the groups formed are anthracene groups that may have substituents, etc.

[0226] Examples of anthracene compounds represented by this formula (1) include compounds represented by any of the following formulas.

[0227] [Chemistry 38]

[0228]

[0229] In each of the aforementioned formulas, X is independently an aryl group that can be substituted with aryl or heteroaryl, or a heteroaryl group that can be substituted with aryl or heteroaryl, and A is independently an arylene group that can be substituted with a single bond, aryl or heteroaryl, or a heteroarylene group that can be substituted with aryl or heteroaryl. Here, regarding aryl and heteroaryl groups, refer to Ar in formula (1) respectively. c Explanation of aryl and heteroaryl groups in etc.

[0230] Preferred examples of the aryl group X in the various formulas include phenyl, 1-naphthyl, 2-naphthyl, etc., and preferred examples of heteroaryl groups include the group represented by formula (A). X is preferably an unsubstituted aryl or an unsubstituted heteroaryl, and when it has substituents, it is preferably substituted by one or two phenyl groups.

[0231] As for the arylene and heteroarylene of A in the various formulas, examples can be listed by removing Ar from formula (1). c The divalent group is obtained by removing any one hydrogen atom from the aryl and heteroaryl groups represented by formula (A). Preferred groups include 1,3-phenylene, 1,4-phenylene, 1,6-naphthylene, 2,5-naphthylene, 2,6-naphthylene, 2,7-naphthylene, and divalent groups obtained by removing any one hydrogen atom from the group represented by formula (A). A is preferably an unsubstituted aryl or unsubstituted heteroaryl, and when substituents are present, it is preferably substituted by one or two phenyl groups.

[0232] As specific examples, the compounds represented by the following formula numbers in Table 1 can be listed: (1-2495), (1-2404), (1-2440), (1-2499), (1-2413), (1-2516), (1-2519), (1-2525), (1-2541), (1-2557), (1-2573), (1-2586), (1-2694), (1-2599), (1-2728), (1-2579), (1-2696), (1-2738), (1-2743). 、(1-2699),(1-2756),(1-2627),(1-2757),(1-2686),(1-2615),(1-2640),(1-2747),(1-2641),(1-2775),(1-2779),(1-2787),(1-2776),(1-2812),(1-3914),(1-3951),(1-3903),(1-2416),(1-2520),(1-2603),(1-3953),(1-3875).

[0233] In addition, as specific examples of "substitutable aryl" and "substitutable heteroaryl", the substituents represented by the structural formulas described later can be listed as explanations of the notations in Table 1.

[0234] At least one hydrogen atom in the compound represented by formula (1) may be substituted with a halogen, a cyano group, or deuterium. Examples of "halogen" in this case include fluorine, chlorine, bromine, and iodine. Compounds in which all hydrogen atoms are substituted with deuterium are particularly preferred.

[0235] In Ar 14 Ar 15 It is a substituted aryl group or a substituted heteroaryl group, and Ar 11 Ar 12 Ar 13 Ar 16 Ar 17 and Ar 18 Among the compounds represented by formula (1) consisting entirely of hydrogen, compounds in which at least one hydrogen atom is substituted by deuterium are preferred. In this case, the substitution position of deuterium is not limited. For example, at least R... c Compounds of deuterium, selected from Ar c and Ar 11 ~Ar 18 Compounds in which at least one hydrogen atom is replaced by deuterium, or compounds in which all hydrogen atoms are replaced by deuterium, etc.

[0236] In equation (1), R cIt is hydrogen, alkyl or cycloalkyl, preferably hydrogen, methyl or tert-butyl, and more preferably hydrogen.

[0237] On the other hand, when Ar 14 Ar 15 Ar is a substituted aryl group or a substituted heteroaryl group. 11 Ar 12 Ar 13 Ar 16 Ar 17 and Ar 18 When all are hydrogen, R can also be listed. c Anthracene compounds that are alkyl or cycloalkyl are preferred examples. Specific examples include the compounds in Table 1 represented by the following formula numbers: (1-4434), (1-4429), (1-4458), (1-4409), (1-4404), and (1-4427).

[0238] In formula (1), Ar is preferred. 11 ~Ar 18 At least two of them are substituted aryl groups or substituted heteroaryl groups. That is, the anthracene compound represented by formula (1) is preferably a structure having at least three substituents bonded to the anthracene ring, selected from the group consisting of substituted aryl groups and substituted heteroaryl groups.

[0239] The anthracene compound represented by formula (1) is more preferably Ar 11 ~Ar 18 Two of them are substituted aryl or substituted heteroaryl, and the other six are hydrogen, substituted alkyl, substituted cycloalkyl, substituted alkenyl or substituted alkoxy. That is, the anthracene compound represented by formula (1) is more preferably a structure having three substituents bonded to the anthracene ring, selected from the group consisting of substituted aryl and substituted heteroaryl.

[0240] The anthracene compounds represented by formula (1) are preferably Ar 11 ~Ar 18 Any two of them are substituted aryl or substituted heteroaryl groups, and the other six are hydrogen, methyl, or tert-butyl. Ar is particularly preferred. 11 ~Ar 18 Any two of them are substituted aryl or substituted heteroaryl, R c It is hydrogen, and Ar 11 ~Ar 18 The other six are hydrogen.

[0241] As a preferred range of anthracene compounds represented by formula (1), anthracene compounds represented by formulas (1A), (1B), (1C), (1D), or (1E) can also be defined.

[0242] [Chemistry 39]

[0243]

[0244] In equations (1A), (1B), (1C), (1D), and (1E), Ar c '、Ar 11 '、Ar 12 '、Ar 13 '、Ar 14 '、Ar 15 '、Ar 17 'and Ar 18 'Each of the following is independently a phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthryl, fluorenyl, benzo[2]fluorenyl, The group consisting of a phenyl group, a triphenylene group, a pyrene group, or a group represented by formula (A) described later, wherein at least one hydrogen atom may be derived from a phenyl group, a biphenyl group, a triphenylene group, a tetraphenylene group, a naphthyl group, a phenanthryl group, a fluorene group, a benzo[a]fluorene group, or a group represented by a phenyl group, a triphenylene group, a phenylene group, a phenylene group, a Substitution with methyl, triphenyl, pyrene, or the methyl group represented by formula (A) described later. Here, when the hydrogens of the methylene group in both the fluorenyl and benzo[a]fluorenyl groups are substituted with phenyl groups, these phenyl groups can be bonded to each other via single bonds. In unbonded Ar c '、Ar 11 '、Ar 12 '、Ar 13 '、Ar 14 '、Ar 15 '、Ar 17 'and Ar 18 Methyl or tert-butyl groups can be bonded to the carbon atoms of the anthracene ring to replace hydrogen.

[0245] When Ar c '、Ar 11 '、Ar 12 '、Ar 13 '、Ar 14 '、Ar 15 '、Ar 17 'and Ar 18 When the radical is a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group, it is preferably a radical represented by any one of the formulas (1-X1) to (1-X7).

[0246] Ar c '、Ar 11 '、Ar 12 '、Ar 13'、Ar 14 '、Ar 15 '、Ar 17 'and Ar 18 More preferably, each is a phenyl, biphenyl (especially biphenyl-2-yl or biphenyl-4-yl), terphenyl (especially meta-terphenyl-5'-yl), naphthyl, phenanthryl, fluorenyl, or any of the formulas (A-1) to (A-4) described later, wherein at least one hydrogen atom in these groups may be substituted by a phenyl, biphenyl, naphthyl, phenanthryl, fluorenyl, or any of the formulas (A-1) to (A-4) described later.

[0247] In addition, at least one hydrogen atom in the compound represented by formula (1A), formula (1B), formula (1C), formula (1D) or formula (1E) may be substituted with halogen, cyano or deuterium.

[0248] The basis represented by equation (A) will be explained below.

[0249] [Chemistry 40]

[0250]

[0251] In equation (A), Y is -O-, -S-, or >NR. 39 R 39 It is hydrogen or a substituted aryl group. Additionally, in formula (A), R... 21 ~R 28 Each of the following is independently hydrogen, a substituted alkyl group, a substituted cycloalkyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, a substituted amino group, a halogen, a hydroxyl group, or a cyano group, R. 21 ~R 28 The adjacent groups can bond with each other to form a hydrocarbon ring, aryl ring, or heteroaryl ring. Furthermore, at least one hydrogen atom in the formed hydrocarbon ring, aryl ring, or heteroaryl ring can be substituted with a substituted alkyl group, a substituted cycloalkyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, a substituted amino group, a halogen group, a hydroxyl group, or a cyano group.

[0252] The base represented by formula (A) is obtained by removing a hydrogen atom from any position in formula (A), where * indicates the position.

[0253] R in equation (A) 21 ~R 28Preferably, all of them are hydrogen, or at least one is a substituted aryl or substituted heteroaryl, more preferably all of them are hydrogen, or at least one is a substituted aryl or substituted heteroaryl and the others are hydrogen, and even more preferably all of them are hydrogen, or any one or two are substituted aryl or substituted heteroaryl and the others are hydrogen. When R 21 ~R 28 When adjacent groups bond to each other to form a hydrocarbon ring, aryl ring, or heteroaryl ring, it is preferable that the hydrogens in the formed ring are not substituted by substituents and the remaining R groups are not substituted. 21 ~R 28 It is hydrogen, or the substituents that replace hydrogen in the ring formed and the remaining R 21 ~R 28 At least one of them is a substituted aryl or a substituted heteroaryl, more preferably, the hydrogen in the formed ring is not substituted by a substituent and the remaining R 21 ~R 28 It is hydrogen, or the substituents that replace hydrogen in the ring formed and the remaining R 21 ~R 28 One or both of them are substituted aryl or substituted heteroaryl.

[0254] As R in equation (A) 21 ~R 28 The "alkyl" in "substitutable alkyl" can be either straight-chain or branched, for example, straight-chain alkyl with 1 to 24 carbon atoms or branched alkyl with 3 to 24 carbon atoms. Preferably, it is an alkyl with 1 to 18 carbon atoms (branched alkyl with 3 to 18 carbon atoms), more preferably an alkyl with 1 to 12 carbon atoms (branched alkyl with 3 to 12 carbon atoms), even more preferably an alkyl with 1 to 6 carbon atoms (branched alkyl with 3 to 6 carbon atoms), and particularly preferably an alkyl with 1 to 4 carbon atoms (branched alkyl with 3 to 4 carbon atoms).

[0255] Specific examples of "alkyl groups" include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc.

[0256] As R in equation (A) 21 ~R 28The "aryl" in "substitutable aryl" can be exemplified by aryl groups having 6 to 30 carbon atoms, preferably aryl groups having 6 to 16 carbon atoms, more preferably aryl groups having 6 to 12 carbon atoms, and particularly preferably aryl groups having 6 to 10 carbon atoms.

[0257] Specific examples of "aryl" groups include: phenyl as a monocyclic compound; biphenyl as a bicyclic compound; naphthyl as a condensed bicyclic compound; terphenyl as a tricyclic compound (m-terphenyl, o-terphenyl, p-terphenyl); anthracene, acenaphthene, fluorenyl, phenatenyl, and phenanthrene as condensed tricyclic compounds; triphenylene, pyrene, tetraphenyl, and benzofluorenyl as condensed tetracyclic compounds; and perylene and pentaphenyl as condensed pentacyclic compounds.

[0258] As R in equation (A) 21 ~R 28 The term "heteroaryl" in "substitutable heteroaryl" can include, for example, heteroaryl groups with 2 to 30 carbon atoms, preferably heteroaryl groups with 2 to 25 carbon atoms, more preferably heteroaryl groups with 2 to 20 carbon atoms, and even more preferably heteroaryl groups with 2 to 15 carbon atoms, particularly preferably heteroaryl groups with 2 to 10 carbon atoms. Furthermore, examples of heteroaryl groups include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-forming atoms, in addition to carbon atoms.

[0259] Specific examples of "heteroaryl" groups include: pyrrole, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazole, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, indole, isoyindole, 1H-indazole, benzimidazole, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, and iso... Quinolinyl, cinolinyl, quinazolinyl, quinoxolinyl, phthalazinyl, naphthidyl, purineyl, pteridinyl, carbazoyl, acridineyl, phenoxthiayl, phenoxazinyl, phenthiazinyl, phenazinyl, inazinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiophenyl, benzo[b]thiophenyl, dibenzothiophenyl, furazinyl, thiathenyl, naphthobenzofuranyl, naphthobenzothiophenyl, etc.

[0260] As R in equation (A) 21 ~R 28 The "alkoxy group" in "substitutable alkoxy group" can include, for example, straight-chain alkoxy groups with 1 to 24 carbon atoms or branched-chain alkoxy groups with 3 to 24 carbon atoms. Preferably, it is an alkoxy group with 1 to 18 carbon atoms (branched-chain alkoxy groups with 3 to 18 carbon atoms), more preferably an alkoxy group with 1 to 12 carbon atoms (branched-chain alkoxy groups with 3 to 12 carbon atoms), and even more preferably an alkoxy group with 1 to 6 carbon atoms (branched-chain alkoxy groups with 3 to 6 carbon atoms), and particularly preferably an alkoxy group with 1 to 4 carbon atoms (branched-chain alkoxy groups with 3 to 4 carbon atoms).

[0261] Specific examples of "alkoxy groups" include: methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentoxy, hexoxy, heptoxy, octoxy, etc.

[0262] As R in equation (A) 21 ~R 28 The "aryloxy group" in "substitutable aryloxy group" refers to a group in which the hydrogen of the -OH group is replaced by an aryl group, and the aryl group can be used as R. 21 ~R 28 The "aryl" in the text refers to the base.

[0263] As R in equation (A) 21 ~R 28 The "arylthio" in "substitutable arylthio" refers to a group in which the hydrogen of the -SH group is replaced by an aryl group, and the aryl group can be used as R. 21 ~R 28 The "aryl" in the text refers to the base.

[0264] As R in equation (A) 21 ~R 28 The term "trialkylsilyl" can be an example of a silyl group in which each of the three hydrogens is independently replaced by an alkyl group, and the alkyl group can be referred to as R. 21 ~R 28 The "alkyl" in the text refers to the group. For substitution, the preferred alkyl group is an alkyl group having 1 to 4 carbon atoms, specifically including: methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, cyclobutyl, etc.

[0265] Specific examples of "trialkylsilyl" include: trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, tritert-butylsilyl, ethyl dimethylsilyl, propyl dimethylsilyl, isopropyl dimethylsilyl, butyl dimethylsilyl, sec-butyl dimethylsilyl, tert-butyl dimethylsilyl, methyl diethylsilyl, propyl diethylsilyl, isopropyl diethylsilyl, butyl diethylsilyl, sec-butyl diethylsilyl, tert-butyl diethylsilyl, methyl dipropylsilyl, ethyl dipropylsilyl, butyl dipropylsilyl, sec-butyl dipropylsilyl, tert-butyl diisopropylsilyl, methyl diisopropylsilyl, ethyl diisopropylsilyl, butyl diisopropylsilyl, sec-butyl diisopropylsilyl, tert-butyl diisopropylsilyl, etc.

[0266] As R in equation (A) 21 ~R 28The term "substituted amino group" in the phrase "substituteable amino group" can include, for example, amino groups in which two hydrogen atoms are substituted by an aryl or heteroaryl group. An amino group in which two hydrogen atoms are substituted by an aryl group is a diaryl-substituted amino group, an amino group in which two hydrogen atoms are substituted by a heteroaryl group is a dihexanel-substituted amino group, and an amino group in which two hydrogen atoms are substituted by both an aryl and a heteroaryl group is an arylhexanel-substituted amino group. The aryl or heteroaryl group can be referenced as R. 21 ~R 28 The group is described by the "aryl" or "heteroaryl" in the text.

[0267] Specific examples of "substituted amino groups" include: diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, etc.

[0268] As R in equation (A) 21 ~R 28 The "halogens" mentioned include: fluorine, chlorine, bromine, and iodine.

[0269] As R in equation (A) 21 ~R 28 Among the groups described, some may also be substituted as described above. Examples of substituents in this case include alkyl, aryl, or heteroaryl groups. The alkyl, aryl, or heteroaryl groups may be referred to as R. 21 ~R 28 The "alkyl", "aryl", or "heteroaryl" groups are used to indicate the group.

[0270] As Y in equation (A) > NR 39 R in " 39 The aryl group is hydrogen or a substituted aryl group, and the aryl group can be referenced as R. 21 ~R 28 The "aryl" in the text refers to the group, and furthermore, as the substituent, it can be cited as a group targeting R. 21 ~R 28 The base is explained by the substituent.

[0271] R in equation (A) 21 ~R 28 The adjacent groups can bond to each other to form a hydrocarbon ring, aryl ring, or heteroaryl ring. The group that does not form a ring is represented by the group in formula (A-1) below; for example, the groups represented by formulas (A-2) to (A-14) below can be listed as ring-forming groups. Furthermore, at least one hydrogen atom in any of the groups represented by formulas (A-1) to (A-14) can be substituted by an alkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxyl, or cyano group, which can be referred to as R. 21 ~R28 The bases described are those that are explained by the bases in the text.

[0272] A ring formed by the mutual bonding of adjacent groups can be a hydrocarbon ring, for example, a cyclohexane ring; or an aryl ring or a heteroaryl ring, for example, the aforementioned R... 21 ~R 28 The ring structures described in “aryl” or “heteroaryl” are formed by condensation with one or both benzene rings of formula (A-1).

[0273] As a basis represented by formula (A), for example, any of the following formulas (A-1) to (A-14) can be used as a basis, preferably any of the formulas (A-1) to (A-11), more preferably any of the formulas (A-1) to (A-4), and even more preferably any of the formulas (A-1), (A-3) and (A-4), and most preferably the basis represented by formula (A-1).

[0274] [Chemistry 41]

[0275]

[0276] The base represented by formula (A) is obtained by removing a hydrogen atom from any position in formula (A), where * indicates the position. That is, the base represented by formula (A) can use any position as the bonding position. Preferably, it is any carbon atom on the two benzene rings in the structure of formula (A), or R in the structure of formula (A). 21 ~R 28 Atoms on any ring formed by the mutual bonding of adjacent bases, or atoms in the structure of formula (A) acting as Y > NR 39 The base of N direct bonds (which have bonded bonds in these).

[0277] In formula (A), Y and Y in each of formulas (A-1) to (A-14) are preferably -O-.

[0278] As a basis represented by equation (A), for example, bases represented by the following equations can be listed. Y and * in the equations have the same definition as described above, and Y is preferably -O-.

[0279] [Chemistry 42]

[0280]

[0281] Compounds containing the group represented by formula (A) (especially the group represented by formula (A) where Y is -O-) can be listed as preferred examples of anthracene compounds represented by formula (1). In addition to the compounds already described, the following anthracene compounds (a) or (b) are also preferred.

[0282] (a) In equation (1), Ar 14 Ar 15 Ar is a substituted aryl group or a substituted heteroaryl group. 11 Ar 12 Ar 13 Ar 16 Ar 17 and Ar 18 All are hydrogen, selected from Ar c Ar 14 and Ar 15 At least one of the groups formed is a basis represented by equation (A), and R is chosen from equation (A). 21 ~R 28 And Y is greater than NR 39 R in the case 39 At least one of the groups consists of an aryl or heteroaryl anthracene compound. R c Hydrogen is preferred.

[0283] As specific examples, the compounds represented by the following formula numbers in Table 1 can be listed: (1-3445), (1-3467), (1-3434), (1-3481), (1-3408), (1-3777), (1-3594), (1-3589), (1-3440), (1-3435), (1-3572), (1-3453), (1-3562), (1-3559), (1-3522), (1-4014), (1-4018), (1-3762), (1-4145), (1-4573), (1-4579), (1-3444), (1-3450), (1-4747).

[0284] (b) In equation (1), Ar 14 Ar 15 Ar is a substituted aryl group or a substituted heteroaryl group. 11 Ar 12 Ar 13 Ar 16 Ar 17 and Ar 18 All are hydrogen, and are selected from Ar c Ar 14 and Ar 15 At least one of the groups consists of an anthracene compound having an aryl group as a substituent of the group represented by formula (A) or a heteroaryl group as a substituent of the group represented by formula (A). R cHydrogen is preferred. Examples of aryl groups having the group represented by formula (A) as a substituent include groups represented by any one of formulas (1-X1) to (1-X6), where Ar in the formula... 21 Ar 22 Ar 23 Ar 24 Ar 25 Or Ar 26 It is the basis represented by equation (A).

[0285] As specific examples, the compounds represented by the following formula numbers in Table 1 can be listed: (1-2912), (1-3284), (1-3736), (1-3770), (1-2873), (1-3249), (1-3296), (1-2917), (1-3768), (1-3780), (1-3963), (1-4112), (1-4052), (1-4047), (1-3778), (1-4168), (1-4510).

[0286] The bases represented by formula (B), (C), (D), and (E) will be explained below. The explanation of each substituent below can be found in R of formula (A). 21 ~R 28 Explanation.

[0287] [Chemistry 43]

[0288]

[0289] In equation (B), Y is -O-, -S-, or >NR. 39 R 39 It is hydrogen or a substituted aryl group. Additionally, in formula (B), R... 29 ~R 38 Each of the following is independently hydrogen, a substituted alkyl group, a substituted cycloalkyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, a substituted amino group, a halogen, a hydroxyl group, or a cyano group, R. 29 ~R 38The adjacent groups can bond to each other to form a hydrocarbon ring, aryl ring, or heteroaryl ring. Furthermore, at least one hydrogen atom in the formed hydrocarbon ring, aryl ring, or heteroaryl ring can be substituted by a substituted alkyl group, a substituted cycloalkyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, a substituted amino group, a halogen, a hydroxyl group, or a cyano group. The group represented by formula (B) is obtained by removing a hydrogen atom from any position in formula (B), where * indicates the position.

[0290] In formula (B), Y is preferably -O-.

[0291] R in equation (B) 29 ~R 38 Preferably, all of them are hydrogen, or at least one is a substituted aryl or substituted heteroaryl, more preferably all of them are hydrogen, or at least one is a substituted aryl or substituted heteroaryl and the others are hydrogen, and even more preferably all of them are hydrogen, or any one or two are substituted aryl or substituted heteroaryl and the others are hydrogen. When R 29 ~R 38 When adjacent groups bond to each other to form a hydrocarbon ring, aryl ring, or heteroaryl ring, it is preferable that the hydrogens in the formed ring are not substituted by substituents and the remaining R groups are not substituted. 29 ~R 38 It is hydrogen, or the substituents that replace hydrogen in the ring formed and the remaining R 29 ~R 38 At least one of them is a substituted aryl or a substituted heteroaryl, more preferably, the hydrogen in the formed ring is not substituted by a substituent and the remaining R 29 ~R 38 It is hydrogen, or the substituents that replace hydrogen in the ring formed and the remaining R 29 ~R 38 One or both of them are substituted aryl or substituted heteroaryl.

[0292] As a basis represented by equation (B), for example, the basis represented by equation (B-1) can be listed below.

[0293] [Chemistry 44]

[0294]

[0295] As a basis represented by equation (B), more specifically, examples can be listed of bases represented by the following equations. Y and * in the equations have the same definitions as described above, and Y is preferably -O-.

[0296] [Chemistry 45]

[0297]

[0298] In equation (C), Y is -O-, -S-, or >NR. 39 R 39 It is hydrogen or a substituted aryl group. Additionally, in formula (C), R... 41 ~R 48 Each of the following is independently hydrogen, a substituted alkyl group, a substituted cycloalkyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, a substituted amino group, a halogen, a hydroxyl group, or a cyano group, R. 41 ~R 48 The adjacent groups can bond with each other to form a hydrocarbon ring, aryl ring, or heteroaryl ring. Furthermore, at least one hydrogen atom in the formed hydrocarbon ring, aryl ring, or heteroaryl ring can be substituted with a substituted alkyl group, a substituted cycloalkyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, a substituted amino group, a halogen group, a hydroxyl group, or a cyano group.

[0299] The base represented by formula (C) is obtained by removing a hydrogen atom from any position in formula (C), where * indicates the position.

[0300] In equation (C), when Y is > NR 39 At that time, R 39 Preferably, it is a substituted phenyl group, more preferably an unsubstituted phenyl group. As R 39 The substituted phenyl group can convert R 42 R 43 R 46 or R 47 It acts as a bonding bond with the benzene ring. Preferably, at least one of Y is -O-, more preferably both Y are -O-, or one Y is -O- and the other is >NR. 39 R is preferred. 41 ~R 48 Both are hydrogen.

[0301] As a basis represented by equation (C), for example, the basis represented by equation (C-1) can be listed below.

[0302] [Chemistry 46]

[0303]

[0304] As a basis represented by equation (C), more specifically, examples can be given by the basis represented by the following equation. Y and * in the equation have the same definition as described above, and Y is preferably -O-.

[0305] [Chemistry 47]

[0306]

[0307] In equation (D), Y is -O-, -S-, or >NR. 39 R 39 It is hydrogen or a substituted aryl group. Additionally, in formula (D), R... 51 ~R 58 Each of the following is independently hydrogen, a substituted alkyl group, a substituted cycloalkyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, a substituted amino group, a halogen, a hydroxyl group, or a cyano group, R. 51 ~R 58 The adjacent groups can bond with each other to form a hydrocarbon ring, aryl ring, or heteroaryl ring. Furthermore, at least one hydrogen atom in the formed hydrocarbon ring, aryl ring, or heteroaryl ring can be substituted with a substituted alkyl group, a substituted cycloalkyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, a substituted amino group, a halogen group, a hydroxyl group, or a cyano group.

[0308] The base represented by formula (D) is obtained by removing a hydrogen atom from any position in formula (D), where * indicates the position.

[0309] In formula (D), Y is preferably -O-. R is preferred. 51 ~R 58 Both are hydrogen.

[0310] In equation (E), Y is -O-, -S-, or >NR. 39 R 39 It is hydrogen or a substituted aryl group. Additionally, in formula (E), R... 61 ~R 71 Each of the following is independently hydrogen, a substituted alkyl group, a substituted cycloalkyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, a substituted amino group, a halogen, a hydroxyl group, or a cyano group, R. 61 ~R 71The adjacent groups can bond with each other to form a hydrocarbon ring, aryl ring, or heteroaryl ring. Furthermore, at least one hydrogen atom in the formed hydrocarbon ring, aryl ring, or heteroaryl ring can be substituted with a substituted alkyl group, a substituted cycloalkyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, a substituted amino group, a halogen group, a hydroxyl group, or a cyano group.

[0311] The base represented by formula (E) is obtained by removing a hydrogen atom from any position in formula (E), where * indicates the position.

[0312] In equation (E), when Y is > NR 39 At that time, R 39 Preferably, it is a substituted phenyl group, more preferably an unsubstituted phenyl group. As R 39 The substituted phenyl group can convert R 61 R 62 R 69 or R 70 It acts as a bonding bond to the benzene ring. Y is preferably at least one of -O-, more preferably all of them are -O-. R 61 ~R 71 Preferably, it is hydrogen, phenyl, biphenyl or naphthyl, and more preferably all of the same kind is hydrogen.

[0313] As particularly preferred anthracene compounds represented by formula (1), examples of anthracene compounds represented by formula (1Aa) are listed below.

[0314] [Chemistry 48]

[0315]

[0316] In equation (1Aa), Ar c '、Ar 14 'and Ar 15 'Each of the following groups is independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, benzo[2]fluorenyl, The group may be represented by a phenyl group, a triphenylene group, a pyrene group, or a group of any of the formulas (A-1) to (A-11), wherein at least one hydrogen atom in these groups may be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorene group, a benzo[a]fluorene group, or a group of other phenyl groups. Substitution of the methyl group, triphenylene, pyrene, or any of the methyl groups represented by formulas (A-1) to (A-11). Here, when the hydrogens of the methylene group in both the fluorene group and the benzo[a]fluorene group are substituted with phenyl groups, these phenyl groups can be bonded to each other via single bonds. Additionally, in the unbonded Ar... c '、Ar 14 'and Ar 15On the anthracene ring, a methyl or tert-butyl group may be substituted to replace hydrogen. At least one hydrogen atom in the compound represented by formula (1Aa) may be substituted by a halogen or cyano group, and at least one hydrogen atom in the compound represented by formula (1Aa) may be substituted by a deuterium group.

[0317] In equation (1Aa), Ar c '、Ar 14 'and Ar 15 'Each is preferably a group represented by phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl or any of the groups (A-1) to (A-4), wherein at least one hydrogen atom of these groups may be substituted by a group represented by phenyl, naphthyl, phenanthryl, fluorenyl or any of the groups (A-1) to (A-4).'

[0318] In the compound represented by formula (1Aa), it is preferred to bond at least the carbon at position 10 of the anthracene ring (Ar) to the anthracene ring. c The hydrogen atom in the 9-position bond (considered as carbon at position 9) is replaced with deuterium. That is, the compound represented by formula (1Aa) is preferably the compound represented by formula (1Ab). Furthermore, in formula (1Ab), D is deuterium, and Ar... c '、Ar 14 'and Ar 15 'Same as the definition in formula (1Aa). In formula (1Ab), D indicates that at least the position is deuterium, and any one or more other hydrogens in formula (1Aa) can be deuterium at the same time, and preferably all hydrogens in formula (1Aa) are deuterium.

[0319] [Chemistry 49]

[0320]

[0321] The following Table 1 shows specific examples of compounds represented by formulas (1-1) to (1-5179) that represent formula (1). However, the present invention is not limited to the disclosure of these specific structures. In Table 1, D represents deuterium, Me represents methyl, tBu represents tert-butyl, CyHex represents cyclohexyl, and other notations will be described later.

[0322] [Table 1]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

[0410] The substituents represented by the symbols used in Table 1 are shown below. When the symbol for Y is O in the structural formula of the substituent shown below is listed in Table 1, it indicates that -Y- in the structural formula is a -O- substituent (e.g., HCO-1); when the symbol for Y is S is listed in Table 1, it indicates that -Y- in the structural formula is a -S- substituent (e.g., HCS-1); and when the symbol for Y is N is listed in Table 1, it indicates that -Y- in the structural formula is a >N-Ph (Ph is phenyl) substituent (e.g., HCN-1). Additionally, when the notation for Z is O in the structural formulas shown below, as listed in Table 1, it indicates that -Z- in the structural formula is a -O- substituent (e.g., DHCO-1); when the notation for Z is S in Table 1, it indicates that -Z- in the structural formula is a -S- substituent (e.g., DHCS-1); and when the notation for Z is N in Table 1, it indicates that -Z- in the structural formula is a substituent of >N-C6D5 (e.g., DHCN-1). Furthermore, in the following structural formulas, D represents deuterium, Me represents methyl, tBu represents tert-butyl, and * indicates the bond position.

[0411] [Transformation 50]

[0412]

[0413] [Chemistry 51]

[0414]

[0415] [Chemistry 52]

[0416]

[0417] [Chemistry 53]

[0418]

[0419] [Chemistry 54]

[0420]

[0421] [Chemistry 55]

[0422]

[0423] [Chemistry 56]

[0424]

[0425] [Chemistry 57]

[0426]

[0427] [Chem.58]

[0428]

[0429] [Chemistry 59]

[0430]

[0431] [Transformation 60]

[0432]

[0433] [Chemistry 61]

[0434]

[0435] [Chemistry 62]

[0436]

[0437] [Chemistry 63]

[0438]

[0439] [Chemistry 64]

[0440]

[0441] [Chemistry 65]

[0442]

[0443] [Chemistry 66]

[0444]

[0445] [Chemistry 67]

[0446]

[0447] [Chemistry 68]

[0448]

[0449] [Chemistry 69]

[0450]

[0451] [Chemistry 70]

[0452]

[0453] [Chemistry 71]

[0454]

[0455] [Chemistry 72]

[0456]

[0457] [Chemistry 73]

[0458]

[0459] [Chemistry 74]

[0460]

[0461] [Chemistry 75]

[0462]

[0463] [Chemistry 76]

[0464]

[0465] [Chemistry 77]

[0466]

[0467] [Chemistry 78]

[0468]

[0469] [Chemistry 79]

[0470]

[0471] [Chemistry 80]

[0472]

[0473] [Chemistry 81]

[0474]

[0475] [Chemistry 82]

[0476]

[0477] [Chemistry 83]

[0478]

[0479] [Chemistry 84]

[0480]

[0481] [Chemistry 85]

[0482]

[0483] [Chemistry 86]

[0484]

[0485] [Chemistry 87]

[0486]

[0487] [Chemistry 88]

[0488]

[0489] [Chemistry 89]

[0490]

[0491] [Chemistry 90]

[0492]

[0493] [Chemistry 91]

[0494]

[0495] [Chemistry 92]

[0496]

[0497] [Chemistry 93]

[0498]

[0499] The preferred compounds are those represented by the following formula: In the following formula, D represents deuterium, Me represents methyl, tBu represents tert-butyl, and CyHex represents cyclohexyl.

[0500] [Chemistry 94]

[0501]

[0502] [Chemistry 95]

[0503]

[0504] [Chemistry 96]

[0505]

[0506] [Chemistry 97]

[0507]

[0508]

[0509] [Chem. 98]

[0510]

[0511] [Chemistry 99]

[0512]

[0513] [Chemistry 100]

[0514]

[0515] [Chemistry 101]

[0516]

[0517] [Chemistry 102]

[0518]

[0519] [Chemistry 103]

[0520]

[0521] [Chemistry 104]

[0522]

[0523] [Chemistry 105]

[0524]

[0525] [Chemistry 106]

[0526]

[0527] [Chemistry 107]

[0528]

[0529] [Chemistry 109]

[0530]

[0531] [Chemical 110]

[0532]

[0533] [Chemistry 111]

[0534]

[0535] [Chemistry 112]

[0536]

[0537] [Chemistry 113]

[0538]

[0539] [Chemistry 114]

[0540]

[0541] [Chemistry 115]

[0542]

[0543] [Chemistry 116]

[0544]

[0545] [Chemistry 117]

[0546]

[0547] [Chemistry 118]

[0548]

[0549] [Chemistry 119]

[0550]

[0551] [Chemistry 120]

[0552]

[0553] [Chemistry 121]

[0554]

[0555] [Chemistry 122]

[0556]

[0557] [Chemistry 123]

[0558]

[0559] 1-1-2. Preparation methods of anthracene compounds

[0560] The anthracene compounds represented by formula (1) can be manufactured by means of the manufacturing methods described in International Publication No. 2006 / 003842, Korean Patent Publication No. 2017-116885, International Publication No. 2009 / 142230, etc.

[0561] 1-2-1. Polycyclic aromatic compounds and their polymers represented by formula (2)

[0562] The organic EL element of the present invention comprises, in the light-emitting layer, a polycyclic aromatic compound represented by formula (2) and polymers of polycyclic aromatic compounds having a plurality of structures represented by formula (2) as dopant materials. The polycyclic aromatic compound is preferably a polycyclic aromatic compound represented by formula (2-a), (2-b), (2-c), (2-d), (2-e), or (2-f) or a polymer of polycyclic aromatic compounds having a plurality of structures represented by formula (2-a), (2-b), (2-c), (2-d), (2-e), or (2-f).

[0563] [Chemistry 124]

[0564]

[0565]

[0566] In addition, in each structural formula, “A” to “C” and “a” to “c” are symbols representing ring structures represented by rings, benzene rings or five-membered rings, respectively, and other symbols are the same as those defined above.

[0567] In formula (2), rings A, B, and C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted by a substituent. The substituent is preferably a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, a substituted or unsubstituted arylheteroarylamino group (an amino group having both an aryl and a heteroaryl group), a substituted or unsubstituted diarylboroyl group (where the two aryl groups may be bonded via a single bond or a linker), a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryloxy group, or a substituted silyl group. Examples of substituents that may be used when these groups have substituents include: aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl.

[0568] In formula (2), rings A, B, and C are independently aryl or heteroaryl rings. At least one hydrogen atom in these rings may be substituted by a substituent.

[0569] Ring A, ring B, and ring C are preferably at least one of an aryl ring having at least one substituent or a heteroaryl ring having at least one substituent. More preferably, ring A, ring B, and ring C are all aryl rings having at least one substituent or heteroaryl rings having at least one substituent. More preferably, ring A, ring B, and ring C are each an aryl ring having one substituent or a heteroaryl ring having one substituent.

[0570] Preferred substituents at this time include substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted diarylamino groups, substituted or unsubstituted diheteroarylamino groups, substituted or unsubstituted arylheteroarylamino groups (amino groups having both aryl and heteroaryl groups), substituted or unsubstituted diarylboroyl groups (where the two aryl groups may be bonded via a single bond or a linker), substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryloxy groups, or substituted silyl groups. Examples of substituents that are substituents in cases where these groups have substituents include: aryl, heteroaryl, alkyl, cycloalkyl, diarylamino, and substituted silyl groups.

[0571] In particular, substituted or unsubstituted alkyl groups (especially neopentyl) and cycloalkyl groups such as adamantyl are preferred as substituents. Tertiary alkyl groups (tR) are also preferred. This is because such bulky substituents prevent deactivation caused by molecular aggregation, thus increasing the photoluminescence quantum yield (PLQY). Furthermore, substituted or unsubstituted diarylamino groups are also preferred as substituents.

[0572] The tertiary alkyl group is represented by the following formula (tR).

[0573] [Chemistry 125]

[0574]

[0575] In equation (tR), R a R b and R c Each is an alkyl group having 1 to 24 carbon atoms, wherein any -CH2- in the alkyl group may be substituted with -O-, and the group represented by formula (tR) is substituted at * with at least one hydrogen atom in the compound or structure represented by formula (2).

[0576] As R a R b and R cThe term "alkyl group having 1 to 24 carbon atoms" can be either straight-chain or branched. Examples include straight-chain alkyl groups having 1 to 24 carbon atoms, branched alkyl groups having 3 to 24 carbon atoms, alkyl groups having 1 to 18 carbon atoms (branched alkyl groups having 3 to 18 carbon atoms), alkyl groups having 1 to 12 carbon atoms (branched alkyl groups having 3 to 12 carbon atoms), alkyl groups having 1 to 6 carbon atoms (branched alkyl groups having 3 to 6 carbon atoms), and alkyl groups having 1 to 4 carbon atoms (branched alkyl groups having 3 to 4 carbon atoms).

[0577] In equation (2), R in equation (tR) a R b and R c The total number of carbons is preferably 3 to 20, and more preferably 3 to 10.

[0578] As R a R b and R c Specific alkyl groups include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc.

[0579] Examples of groups represented by formula (tR) include: tert-butyl, tert-pentyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,3,3-tetramethylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-Ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl, etc. Among these, tert-butyl and tert-pentyl are preferred.

[0580] Other preferred examples of substituents in rings A, B, and C include diarylamino groups substituted with a group of formula (tR), carbazolyl groups substituted with a group of formula (tR), or benzocarbazolyl groups substituted with a group of formula (tR). Regarding "diarylamino group," groups described below as "first substituents" can be listed. Examples of substitution forms of the group of formula (tR) for diarylamino, carbazolyl, and benzocarbazolyl groups, where some or all of the hydrogen atoms in the aryl ring or benzene ring are substituted with a group of formula (tR), can be listed.

[0581] The aryl ring or heteroaryl ring in rings A, B, and C is preferably associated with the inclusion of "B" or "X". 1 "and "X 2 The central condensed two-ring structure of formula (2) has five- or six-membered rings with bonds.

[0582] Here, the so-called "condensed two-ring structure" refers to the structure shown in the center of equation (2) that includes "B" and "X". 1 "and "X 2 The structure is formed by the condensation of two saturated hydrocarbon rings. Furthermore, the term "six-membered ring sharing bonds with the condensed bicyclic structure" refers, for example, to an a-ring (benzene ring (six-membered ring)) that condenses with the condensed bicyclic structure as shown in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). Additionally, the term "(as ring A) aryl ring or heteroaryl ring having the six-membered ring" means that the A-ring is formed solely by the six-membered ring, or that the A-ring is formed by condensing other rings within the six-membered ring in a manner that includes the six-membered ring. In other words, the "aryl ring or heteroaryl ring having a six-membered ring (as ring A)" mentioned here refers to the condensation of all or part of the six-membered ring constituting the A-ring with the condensed bicyclic structure. The same explanation applies to "five-membered rings." Similarly, the same explanation applies to "B-ring (b-ring)" and "C-ring (c-ring)."

[0583] In formula (2), ring A corresponds to ring a and its substituent R in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). 1 ~Substituent R 3 The B ring in equation (2) corresponds to the b ring and its substituent R in equations (2-a), (2-b), and (2-c). 8 ~Substituent R 11 The b ring in formula (2-d) and its substituent R 10 and substituent R 11 and the b ring and its substituent R in formulas (2-e) and (2-f) 8 and substituent R 9The C ring in equation (2) corresponds to the c ring in equation (2-a) and its substituent R. 4 ~Substituent R 7 The c-ring and its substituent R in formulas (2-b), (2-d), and (2-f) 4 and substituent R 5 and the c ring and its substituent R in formulas (2-c) and (2-e) 6 and substituent R 7 That is, equation (2-a) corresponds to selecting a ring with at least a six-membered ring structure as the structure of rings A to C in equation (2), and equations (2-b), (2-c), (2-d), (2-e), and (2-f) correspond to selecting a ring with at least a six-membered ring structure and a ring with at least a five-membered ring structure as the structure of rings A to C in equation (2), respectively. In this sense, lowercase letters a to c represent each ring in equation (2-a), etc.

[0584] X in equations (2-b), (2-c), (2-d), (2-e), and (2-f) X Each of the above can be independently >O, >S, >NR, or >C(-R)2. Here, the R in >NR is a substituted aryl, a substituted heteroaryl, a substituted alkyl, or a substituted cycloalkyl, preferably a substituted aryl, more preferably an unsubstituted aryl. Additionally, the R in >C(-R)2 can be independently hydrogen, an aryl that can be substituted by an alkyl or cycloalkyl, a heteroaryl that can be substituted by an alkyl or cycloalkyl, an alkyl, or a cycloalkyl, preferably an alkyl, more preferably methyl. The two Rs in >C(-R)2 are preferably the same. Furthermore, the two Rs in >C(-R)2 are also preferably rings formed between each other.

[0585] X X Each of the following is preferred independently: >O, >S, or >NR, more preferably >O or >S, and even more preferably >S.

[0586] In equations (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f), R 1 ~R 11 Each of the following is independently hydrogen, aryl, heteroaryl, diarylamino, diherylamino, arylherylamino, diarylboryl (the two aryl groups may be linked by a single bond or a linker group), alkyl, cycloalkyl, alkoxy, aryloxy or substituted silyl, wherein at least one hydrogen may be substituted by aryl, heteroaryl, alkyl, cycloalkyl or substituted silyl.

[0587] R 1 ~R 11The preferred components are hydrogen, alkyl (especially the tertiary alkyl(tR), neopentyl, etc.), cycloalkyl (e.g., adamantyl, etc.), substituted or unsubstituted diarylamino, or substituted silyl (triphenylsilyl, trimethylsilyl, etc.).

[0588] Preferably, the R values ​​of formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f) are: 1 ~R 3 In this group, 0 to 1 group are non-hydrogen groups (especially the preferred substituents) and the rest are hydrogen groups, R 4 ~R 7 In this group, 0 to 1 group are non-hydrogen groups (especially the preferred substituents) and the rest are hydrogen groups, R 8 ~R 11 In this group, 0 to 1 group are non-hydrogen groups (especially the preferred substituents), and the others are hydrogen.

[0589] More preferably: R 1 ~R 3 In this group, one is a group other than hydrogen (especially the preferred substituents) and the others are hydrogen, R 4 ~R 7 In this group, one is a group other than hydrogen (especially the preferred substituents) and the others are hydrogen, R 8 ~R 11 In this group, one is a group other than hydrogen (especially the preferred substituents) and the others are hydrogen.

[0590] In formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f), the substituent R of rings a, b, and c is... 1 Substituent R 2 Substituent R 3 Substituent R 4 Substituent R 5 Substituent R 6 Substituent R 7 Substituent R 8 Substituent R 9 Substituent R 10 and substituent R 11 The adjacent groups in the ring may be bonded to each other and together with ring a, ring b or ring c to form an aryl ring or a heteroaryl ring. At least one hydrogen in the formed ring may be substituted by an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryl groups may be bonded by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy or substituted silyl, and at least one hydrogen in these groups may be substituted by an aryl, heteroaryl, alkyl, cycloalkyl or substituted silyl.

[0591] For example, the compound represented by formula (2-a) has a different ring structure depending on the bonding morphology of the substituents in rings a, b, and c, as shown in formulas (2-a-1) and (2-a-2) below. In each formula, rings A', B', and C' correspond to rings A, B, and C in formula (2), respectively. Furthermore, R in each formula... 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 and R 11 a, b, c, X 1 and X 2 The definition is the same as that in equation (2-a).

[0592] [Chemistry 126]

[0593]

[0594] If we use equation (2-a) for explanation, then the A' ring, B' ring, and C' ring in equations (2-a-1) and (2-a-2) represent substituents R. 1 Substituent R 2 Substituent R 3 Substituent R 4 Substituent R 5 Substituent R 6 Substituent R 7 Substituent R 8 Substituent R 9 Substituent R 10 and substituent R 11 The adjacent groups in the formula are bonded to each other and form aryl rings or heteroaryl rings with the a, b, and c rings respectively (also referred to as fused rings formed by the condensation of other ring structures with the a, b, or c rings). Furthermore, although not shown in the formula, there are also compounds in which the a, b, and c rings are all transformed into A', B', and C' rings. Additionally, as can be seen from formulas (2-a-1) and (2-a-2), for example, the R of the b ring... 8 R with c ring 7 R of ring b 11 R with ring a 1 R of c ring 4 R with ring a 3 Examples of such bases do not meet the requirement of "adjacent bases are adjacent to each other," and therefore will not form bonds. That is, "adjacent bases" refers to bases that are adjacent to each other on the same ring.

[0595] The compounds represented by formula (2-a-1) or formula (2-a-2) correspond to, for example, the compounds listed below as specific compounds, such as those represented by formulas (2-67) to (2-74), (2-76) to (2-83), (2-273) to (2-276), (2-290) to (2-295) and (2-350) to (2-355). That is, for example, a compound having a benzene ring, indole ring, pyrrole ring, furan ring, thiophene ring, benzofuran ring, benzothiophene ring, cyclopentadiene ring, or indene ring condensed relative to a benzene ring (or b ring, or c ring) in formula (2-a) to form a ring A' (or B' ring, or C' ring), wherein the fused ring A' (or B' ring, or C' ring) formed is a naphthyl ring, carbazole ring, indole ring, benzofuran ring, benzothiophene ring, dibenzofuran ring, dibenzothiophene ring, indene ring, or fluorene ring, respectively.

[0596] Furthermore, in formulas (2-b), (2-c), (2-d), (2-e), and (2-f), other ring structures can also be condensed with ring a, ring b, or ring c to form fused rings. For example, the benzene ring, which is ring a or ring b, can be condensed with other ring structures in the same way as the benzene ring in formula (1-a) to form a fused ring.

[0597] In equations (2-b), (2-c), (2-d), (2-e), and (2-f), it is particularly preferred that R is a five-membered ring that is either a b-ring or a c-ring. 4 ~R 11 Adjacent bases in the equation form fused rings by bonding with each other. For example, in the c-ring of equations (2-b) and (2-c), and the b-ring and c-ring of equations (2-d), (2-e), and (2-f), R... 3 ~R 11 The adjacent groups in the ring can bond together to form a ring, which can form a B' ring or a C' ring as a fused ring. Examples of fused rings in the case where the formed ring is a benzene ring include indole rings, benzofuran rings, and benzothiophene rings. Examples of such structures include compounds represented by any of the formulas (2-572) to (1-588) described later.

[0598] For example, in equations (2-b), (2-c), (2-d), (2-e), and (2-f), for example, when X X When the value is >0, the b ring or c ring becomes a furan ring, and the ring corresponding to the B' ring or C' ring of formula (2-a-1) formed by the condensation of the benzene ring relative to the furan ring is a benzofuran ring.

[0599] Additionally, for example, in equations (2-b), (2-c), (2-d), (2-e), and (2-f), for instance, when X XWhen the value is greater than S, the b ring or c ring becomes a thiophene ring, and the ring formed by the condensation of the benzene ring relative to the thiophene ring, corresponding to the B' ring or C' ring of formula (2-a-1), is a benzothiophene ring.

[0600] As an example, the following shows R in the c-ring, i.e., the quinary ring, of equation (2-b). 4 and R 5 Examples of fused rings formed by bonding together to form benzene rings.

[0601] [Chemistry 127]

[0602]

[0603] In equation (2-b-1), R 1 R 2 R 3 R 8 R 9 R 10 R 11 X X Y 1 X 1 and X 2 The meanings are the same as in equation (2-b), and the preferred ranges are also the same. R 4b R 5b R 6b R 7b The substituent is selected from the group consisting of hydrogen or aryl, heteroaryl, diarylamino, diheterarylamino, arylheterarylamino, diarylboryl (the two aryl groups may be linked by a single bond or a linker), alkyl, cycloalkyl, alkoxy, aryloxy, and substituted silyl, wherein at least one hydrogen in these substituents may be substituted by an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl group. Preferably: R 4b R 5b R 6b R 7b In this formulation, 0 to 2 groups are non-hydrogen substituents and the others are hydrogen, more preferably 1 group is a non-hydrogen substituent and the others are hydrogen. For non-hydrogen substituents, the preferred range can be found in the description of substituents described later as first substituents (which may have second substituents). Particularly preferred non-hydrogen substituents are alkyl groups (especially the aforementioned tertiary alkyl (tR), neopentyl, etc.), cycloalkyl groups (e.g., adamantyl), or substituted or unsubstituted diarylamino groups.

[0604] X in equation (2) 1 and X 2Each of the following can be independently represented as >O, >NR, >C(-R)2, >S, or >Se, where R in >NR is a substituted aryl, substituted heteroaryl, substituted alkyl, or substituted cycloalkyl, and R in >C(-R)2 is hydrogen, a substituted aryl, a substituted alkyl, or a substituted cycloalkyl. The R in >NR and / or the R in >C(-R)2 can be bonded to the B ring and / or C ring via a linking group or a single bond, preferably -O-, -S-, or -C(-R)2-. Furthermore, R in "-C(-R)2-" is hydrogen, alkyl, or cycloalkyl. This description also applies to X in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). 1 and X 2 .

[0605] In equations (2), (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f), X 1 and X 2 Each is preferably >O or >NR, more preferably >NR in which R is a substituted phenyl group, and even more preferably >NR in which at least one R is a phenyl group substituted with one or two tert-butyl, tert-amyl, methyl or phenyl groups, and particularly preferably >NR in which at least one R is a phenyl group substituted with a tert-butyl or tert-amyl group. 1 and X 2 They can be the same base or different bases.

[0606] Here, the provision in equation (2) that “R of >NR and / or R of -C(-R)2- are bonded to ring A, ring B and / or ring C through linker or single bond” corresponds to the provision in equations (2-a), (2-b), (2-c), (2-d), (2-e) and (2-f) that “R of >NR and / or R of -C(-R)2- are bonded to ring a, ring b and / or ring c through -O-, -S-, -C(-R)2- or single bond”.

[0607] The specified provisions may be represented by compounds, which are represented by the following formula (2-a-3-1) and have X. 1 or X 2 The ring structure introduced into fused rings B' and C'. That is, for example, a ring structure with other rings to introduce X. 1 (or X) 2 Compounds that form a B' ring (or C' ring) by condensation of a benzene ring, which is the b ring (or c ring) in formula (2-a). The resulting fused ring B' (or fused ring C') is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0608] Alternatively, the specification can also be represented by a compound, which is represented by formula (2-a-3-2) or formula (2-a-3-3) and has X. 1 and / or X 2 The ring structure introduced into the fused ring A'. That is, for example, a ring structure with other rings to introduce X. 1 (and / or X) 2 Compounds that form an A' ring by condensation of the benzene ring, which is the a ring in formula (2-a), in a manner that allows for the formation of a fused ring A'. The resulting fused ring A' can be, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0609] [Chemistry 128]

[0610]

[0611] The "aryl ring" of rings A, B, and C in formula (2) can be aryl rings with 6 to 30 carbon atoms, preferably aryl rings with 6 to 16 carbon atoms, more preferably aryl rings with 6 to 12 carbon atoms, and particularly preferably aryl rings with 6 to 10 carbon atoms. Furthermore, the "aryl ring" corresponds to the benzene ring in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f), and the "R" ring. 1 ~R 11 "The adjacent groups in the aryl ring are bonded to each other and together with the a-ring, b-ring or c-ring to form an aryl ring."

[0612] Specific examples of "aryl rings" include: benzene rings as monocyclic systems; biphenyl rings as bicyclic systems; naphthalene rings and tetrahydronaphthalene rings as condensed bicyclic systems; terphenyl rings (m-terphenyl, o-terphenyl, p-terphenyl) as tricyclic systems; anthracene rings, acenaphthene rings, fluorene rings, phenaene rings, and phenanthrene rings as condensed tricyclic systems; triphenylene rings, pyrene rings, and tetraphenylene rings as condensed tetracyclic systems; and perylene rings and pentaphenyl rings as condensed pentacyclic systems.

[0613] The "heteroaryl ring" of rings A, B, and C in formula (2) can be exemplified by heteroaryl rings having 2 to 30 carbon atoms, preferably heteroaryl rings having 2 to 25 carbon atoms, more preferably heteroaryl rings having 2 to 20 carbon atoms, and even more preferably heteroaryl rings having 2 to 15 carbon atoms, particularly preferably heteroaryl rings having 2 to 10 carbon atoms. Furthermore, the "heteroaryl ring" can be exemplified by heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring constituent atoms, excluding carbon atoms. Moreover, the "heteroaryl ring" corresponds to the five-membered rings in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f), and the "R" ring. 1 R 2 R 3 R 4 R 5 R6 R 7 R 8 R 9 R 10 and R 11 "The adjacent groups in the ring are bonded to each other and together with the a ring, b ring or c ring to form a heteroaryl ring."

[0614] Specific examples of "heteroaryl rings" include: pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazolium ring, pyrazole ring, pyridine ring, pyrimidine ring, pyrazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, and isoquinoline ring. Cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthidine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxthia ring, phenoxazine ring, phenthiazine ring, phenazine ring, indazine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazan ring, oxadiazole ring, thiathrone ring, etc.

[0615] In this context, the "aryl ring" and "heteroaryl ring" that constitute rings A, B, and C can share a common bond with the condensed bicyclic structure at the center of equation (2) at any position. For example, in the case where the "aryl ring" and "heteroaryl ring" are fused rings of two or more rings, any ring can share a common bond with the condensed bicyclic structure at the center of equation (1). As described above, rings A, B, and C preferably have a common bond with the rings containing B and X. 1 and X 2 The central condensed two-ring structure of equation (2) has a total of five- or six-membered rings with bonds. That is, for example, preferably in equation (2-a), R 1 ~R 3 R 4 ~R 7 and R 8 ~R 11 In the case where adjacent groups are bonded to each other and together with ring a, ring b or ring c to form aryl rings or heteroaryl rings (with the benzene ring as a six-membered ring sharing a bond with the condensed bicyclic structure in the center of formula (2)), and R in formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f) 4 ~R 11 In the case where adjacent groups are bonded to each other and together with rings b and c, form aryl or heteroaryl rings (the five-membered ring shares a bond with the condensed bicyclic structure in the center of equation (2)). Examples of five-membered rings in this case include pyrrole rings, furan rings, and thiophene rings.

[0616] At least one hydrogen atom in the "aryl ring" or "heteroaryl ring" may be a substituted or unsubstituted "aryl" as the first substituent, a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diarylamino", a substituted or unsubstituted "diheteroarylamino", a substituted or unsubstituted "arylheteroarylamino", a substituted or unsubstituted "diarylboryl" (the two aryl groups may be bonded via a single bond or a linker), or a substituted or unsubstituted "alkane". The following can be listed as monovalent groups of "aryl ring" or "heteroaryl ring", including "aryl", ...

[0617] Furthermore, the "alkyl" as the first substituent can be either straight-chain or branched, for example, straight-chain alkyl with 1 to 24 carbon atoms or branched alkyl with 3 to 24 carbon atoms. Preferably, it is an alkyl with 1 to 18 carbon atoms (branched alkyl with 3 to 18 carbon atoms), more preferably an alkyl with 1 to 12 carbon atoms (branched alkyl with 3 to 12 carbon atoms), even more preferably an alkyl with 1 to 6 carbon atoms (branched alkyl with 3 to 6 carbon atoms), and particularly preferably an alkyl with 1 to 5 carbon atoms (branched alkyl with 3 to 5 carbon atoms).

[0618] Specific alkyl groups include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl (t-pentyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc.

[0619] Furthermore, the "cycloalkyl group" as the first substituent can be exemplified by cycloalkyl groups having 3 to 24 carbon atoms, preferably cycloalkyl groups having 3 to 20 carbon atoms, more preferably cycloalkyl groups having 3 to 16 carbon atoms, and even more preferably cycloalkyl groups having 3 to 14 carbon atoms, and even more preferably cycloalkyl groups having 5 to 10 carbon atoms, particularly preferably cycloalkyl groups having 5 to 8 carbon atoms, and most preferably cycloalkyl groups having 5 to 6 carbon atoms.

[0620] Specific examples of cycloalkyl groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and their alkyl (especially methyl) substituted derivatives having 1 to 4 carbon atoms, or norbornyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diadamantyl, decahydronaphthyl, decahydroazyl, etc.

[0621] Furthermore, examples of "alkoxy groups" as the first substituent include straight-chain alkoxy groups having 1 to 24 carbon atoms or branched-chain alkoxy groups having 3 to 24 carbon atoms. Preferably, it is an alkoxy group having 1 to 18 carbon atoms (branched-chain alkoxy groups having 3 to 18 carbon atoms), more preferably an alkoxy group having 1 to 12 carbon atoms (branched-chain alkoxy groups having 3 to 12 carbon atoms), and even more preferably an alkoxy group having 1 to 6 carbon atoms (branched-chain alkoxy groups having 3 to 6 carbon atoms), and particularly preferably an alkoxy group having 1 to 4 carbon atoms (branched-chain alkoxy groups having 3 to 4 carbon atoms).

[0622] Specific examples of alkoxy groups include: methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentoxy, hexoxy, heptoxy, octoxy, etc.

[0623] Furthermore, "substituted silyl" as the first substituent can be exemplified by silyl groups substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl groups. Examples include: trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl.

[0624] As "trialkylsilyl", a group in which each of the three hydrogens in a silyl group is independently replaced by an alkyl group can be listed, and the alkyl group can be the group described as "alkyl" in the first substituent. For substitution, the preferred alkyl group is an alkyl group having 1 to 5 carbon atoms, and specifically, examples include: methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, tert-amyl, etc.

[0625] Specific examples of trialkylsilyl groups include: trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, tritert-butylsilyl, tritert-pentylsilyl, ethyl dimethylsilyl, propyl dimethylsilyl, isopropyl dimethylsilyl, butyl dimethylsilyl, sec-butyl dimethylsilyl, tert-butyl dimethylsilyl, tert-pentyl dimethylsilyl, methyl diethylsilyl, propyl diethylsilyl, isopropyl dimethylsilyl, methyl diethylsilyl, propyl diethyl ... Ethyl silane, butyl diethyl silane, sec-butyl diethyl silane, tert-butyl diethyl silane, tert-pentyl diethyl silane, methyl dipropyl silane, ethyl dipropyl silane, butyl dipropyl silane, sec-butyl dipropyl silane, tert-butyl dipropyl silane, tert-pentyl dipropyl silane, methyl diisopropyl silane, ethyl diisopropyl silane, butyl diisopropyl silane, sec-butyl diisopropyl silane, tert-butyl diisopropyl silane, tert-pentyl diisopropyl silane, etc.

[0626] As "tricycloalkylsilyl", a group in which the three hydrogens of the silyl group are each independently replaced by a cycloalkyl group can be listed, and the cycloalkyl group can be referred to as "cycloalkyl" in the first substituent. The preferred cycloalkyl group for substitution is a cycloalkyl group having 5 to 10 carbon atoms, specifically including: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthyl, decahydroazyl, etc.

[0627] Specific examples of tricycloalkylsilyl groups include tricyclopentylsilyl and tricyclohexylsilyl.

[0628] Specific examples of dialkylcycloalkylsilyl substituted with two alkyl groups and one cycloalkyl group, and alkyldicycloalkylsilyl substituted with one alkyl group and two cycloalkyl groups, can be listed as silyl substituted with groups selected from the specific alkyl and cycloalkyl groups.

[0629] Specific examples of dialkylarylsilyl alkyl substituted with two alkyl groups and one aryl group, alkyldiarylsilyl substituted with one alkyl group and two aryl groups, and triarylsilyl substituted with three aryl groups can be listed as silyl alkyl substituted with the alkyl and aryl groups mentioned above. Specifically, triphenylsilyl alkyl can be listed as a specific example of a triarylsilyl alkyl alkyl group.

[0630] Additionally, the "aryl" in "diarylboryl" as the first substituent can be referenced from the description of the aryl group. Furthermore, the two aryl groups can be bonded via a single bond or a linking group (e.g., >C(-R)2, >O, >S, or >NR). Here, R in >C(-R)2 and >NR is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, or a substituted silyl (the above are the first substituents). In the first substituent, the aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl (the above are the second substituents) can be further substituted. Specific examples of these groups can be referenced from the description of the aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy groups as the first substituents.

[0631] Specifically, the emission wavelength can be adjusted by the steric hindrance, electron-donating, and electron-withdrawing properties of the first substituent. Preferably, the substituent is represented by the following structural formulas, more preferably methyl, tert-butyl, tert-pentyl (t-amyl), tert-octyl, neopentyl, cyclohexyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-trimethylyl, or diphenylamino. The following are preferred: di-p-tolylamino, bis(p-(tert-butyl)phenyl)amino, carbazole, 3,6-dimethylcarbazole, 3,6-di-tert-butylcarbazole, and phenoxy, and more preferably methyl, tert-butyl, tert-pentyl, tert-octyl, neopentyl, adamantyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-trimethylyl, diphenylamino, di-p-tolylamino, bis(p-(tert-butyl)phenyl)amino, carbazole, 3,6-dimethylcarbazole, and 3,6-di-tert-butylcarbazole. From the viewpoint of ease of synthesis, sterically hindered groups are preferred due to their selective synthesis. Specifically, tert-butyl, tert-pentyl (t-amyl), tert-octyl, adamantyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-trimethylyl, di-p-tolylamino, bis(p-(tert-butyl)phenyl)amino, 3,6-dimethylcarbazole, and 3,6-di-tert-butylcarbazole are preferred.

[0632] In the following structural formula, "Me" represents methyl, "tBu" represents tert-butyl, "tAm" represents tert-pentyl, "tOct" represents tert-octyl, and * represents the bond position.

[0633] [Chemistry 129]

[0634]

[0635] [Chemistry 130]

[0636]

[0637] [Chemistry 131]

[0638]

[0639] [Chemistry 132]

[0640]

[0641] [Chemistry 133]

[0642]

[0643] [Chemistry 134]

[0644]

[0645] [Chemistry 135]

[0646]

[0647] [Chemistry 136]

[0648]

[0649]

[0650] [Chemistry 137]

[0651]

[0652]

[0653] [Chemistry 138]

[0654]

[0655] [Chemistry 139]

[0656]

[0657] [Chemistry 140]

[0658]

[0659] [Chemistry 141]

[0660]

[0661] In equations (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f), R is preferred. 1 R 2 R 3 R 4R 5 R 6 R 7 R 8 R 9 R 10 and R 11 One to four of them are groups represented by any of the above structural formulas, and the remainder are hydrogen, more preferably R. 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 and R 11 One to three of them are groups represented by any of the above structural formulas, and the rest are hydrogen, preferably R. 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 and R 11 One to three of them are methyl, tert-butyl, or tert-pentyl, and the rest are hydrogen.

[0662] As a first substituent, at least one hydrogen atom of any of the substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboroyl (the two aryl groups may be bonded via a single bond or a linker)", substituted or unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", or substituted or unsubstituted "aryloxy" as described above, may be substituted or unsubstituted, wherein at least one hydrogen atom may be substituted by a second substituent. Examples of the second substituent include, for example, aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl, with specific examples referring to the description of the monovalent groups of the "aryl ring" or "heteroaryl ring" and the "alkyl", "cycloalkyl", or substituted silyl groups as first substituents. Furthermore, in the case of aryl or heteroaryl groups as second substituents, structures in which at least one hydrogen atom is replaced by an aryl group such as phenyl (specifically, the groups described above), an alkyl group such as methyl (specifically, the groups described above), or a cycloalkyl group such as cyclohexyl (specifically, the groups described above) are also included in the aryl or heteroaryl groups as second substituents. As an example, when the second substituent is a carbazolyl group, a carbazolyl group in which at least one hydrogen atom at the 9-position is replaced by an aryl group such as phenyl, an alkyl group such as methyl, or a cycloalkyl group such as cyclohexyl is also included in the heteroaryl group as second substituents.

[0663] R as in equations (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f) 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 and R 11 The aryl, heteroaryl, aryl of diarylamino, heteroaryl of diarylamino, aryl and heteroaryl of aryl-heteroarylamino, aryl and heteroaryl of diarylboryl or aryloxy groups can be listed as monovalent groups of "aryl ring" or "heteroaryl ring" as described in formula (2). Additionally, as R 1 ~R 11 The alkyl, cycloalkyl, or alkoxy groups in the formula (2) can be referred to in the description of "alkyl," "cycloalkyl," or "alkoxy" as the first substituent. Similarly, the aryl, heteroaryl, alkyl, or cycloalkyl groups that are substituents for these groups are also the same. Additionally, as R... 1 R 2 R 3 R4 R 5 R 6 R 7 R 8 R 9 R 10 and R 11 In cases where adjacent groups are bonded to each other and together with ring a, ring b, or ring c to form an aryl ring or heteroaryl ring, the substituents for these rings are also heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, or aryloxy, as well as aryl, heteroaryl, alkyl, or cycloalkyl as further substituents.

[0664] X in equation (2) 1 and X 2 In the case of >NR, R is an aryl, heteroaryl, alkyl, or cycloalkyl group, and at least one hydrogen atom in the aryl or heteroaryl group may be substituted by an alkyl, cycloalkyl, or a substituted silyl group. Examples of the aryl, heteroaryl, alkyl, and cycloalkyl groups described above are listed. Particularly preferred are aryl groups having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryl groups having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), alkyl groups having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl groups having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). The description also applies to X in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). 1 and X 2 X of equations (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f) 1 and X 2 In the case of >NR, R can be an aryl group of 6 to 12 carbons that can be substituted by an alkyl group of 1 to 6 carbons or a cycloalkyl group of 3 to 14 carbons, a heteroaryl group of 2 to 15 carbons that can be substituted by an alkyl group of 1 to 6 carbons or a cycloalkyl group of 3 to 14 carbons, or an alkyl group of 1 to 6 carbons or a cycloalkyl group of 3 to 14 carbons, preferably an aryl group of 6 to 10 carbons that can be substituted by an alkyl group of 1 to 4 carbons or a cycloalkyl group of 5 to 10 carbons, or an alkyl group of 1 to 4 carbons or a cycloalkyl group of 5 to 10 carbons.

[0665] X in equation (2) 1 and X 2In the case of >C(-R)2, R is hydrogen, aryl, alkyl, or cycloalkyl, and at least one hydrogen atom in the aryl group may be substituted by an alkyl, cycloalkyl, or a substituted silyl group. Examples of the aryl, alkyl, and cycloalkyl groups described above are listed. Particularly preferred are aryl groups having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), alkyl groups having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl groups having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). The description also applies to X in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). 1 and X 2 X of equations (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f) 1 and X 2 In the case of >C(-R)2, R is hydrogen, an aryl group of 6 to 12 carbons that can be substituted by an alkyl group of 1 to 6 carbons or a cycloalkyl group of 3 to 14 carbons, an alkyl group of 1 to 6 carbons or a cycloalkyl group of 3 to 14 carbons, preferably hydrogen, an aryl group of 6 to 10 carbons that can be substituted by an alkyl group of 1 to 4 carbons or a cycloalkyl group of 5 to 10 carbons, an alkyl group of 1 to 4 carbons or a cycloalkyl group of 5 to 10 carbons.

[0666] The R in "-C(-R)2-" as the linking group in formula (2) is hydrogen, alkyl, or cycloalkyl. Examples of the alkyl and cycloalkyl groups described above are listed. Particularly preferred are alkyl groups having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or cycloalkyl groups having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). The same description applies to "-C(-R)2-" as the linking group in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f).

[0667] The dopant material may be a polymer of a polycyclic aromatic compound having a unit structure represented by multiple formulas (2). The polymer is preferably a polymer of a polycyclic aromatic compound having a unit structure represented by multiple formulas (2-a), (2-b), (2-c), (2-d), (2-e), or (2-f). The polymer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and particularly preferably a dimer. The polymer can be any form in which multiple said unit structures are present in a compound. For example, in addition to the form in which multiple said unit structures are bonded by single bonds, alkylene groups with 1 to 3 carbon atoms, phenylene groups, naphthylene groups, etc., it can also be a form in which multiple unit structures are bonded by sharing any ring (A ring, B ring or C ring, a ring, b ring or c ring) contained in the unit structure. In addition, it can also be a form in which any ring (A ring, B ring or C ring, a ring, b ring or c ring) contained in the unit structure is bonded by mutual condensation.

[0668] Examples of such polymers include polymeric compounds represented by formulas (2-4), (2-4-1), (2-4-2), (2-5-1) to (2-5-4), or (2-6). The symbols in these formulas have the same meaning as those in formula (2-a), and the preferred ranges are also the same. If the polymeric compound represented by formula (2-4) is described using formula (2-a), it is a polymeric compound having multiple unit structures represented by formula (2-a) in one compound, with a shared benzene ring as the a ring. Furthermore, if the polymeric compound represented by formula (2-4-1) is described using formula (2-a), it is a polymeric compound having two unit structures represented by formula (2-a) in one compound, with a shared benzene ring as the a ring. Furthermore, if the polymeric compound represented by formula (2-4-2) is described using formula (2-a), it is a polymeric compound having three unit structures represented by formula (2-a) in one compound, with a shared benzene ring as ring a. Furthermore, if the polymeric compounds represented by formulas (2-5-1) to (2-5-4) are described using formula (2-a), they are polymeric compounds having multiple unit structures represented by formula (2) in one compound, with a shared benzene ring as ring b (or ring c). Furthermore, if the polymeric compound represented by formula (2-6) is described using formula (2-a), it is, for example, a polymeric compound having multiple unit structures represented by formula (2-a) in one compound, by condensation of a benzene ring as ring b (or ring a, ring c) as a unit structure with a benzene ring as ring b (or ring a, ring c) as a unit structure.

[0669] [Chemistry 142]

[0670]

[0671] The polymeric compound can be a polymer formed by combining the polymerized form represented by formula (2-4), formula (2-4-1) or formula (2-4-2) with any of formulas (2-5-1) to (2-5-4) or formula (2-6), or a polymer formed by combining the polymerized form represented by any of formulas (2-5-1) to (2-5-4) with the polymerized form represented by formula (2-6), or a polymer formed by combining the polymerized form represented by formula (2-4), formula (2-4-1) or formula (2-4-2) with any of formulas (2-5-1) to (2-5-4) and the polymerized form represented by formula (2-6).

[0672] Furthermore, all or part of the hydrogen in the chemical structure of the polycyclic aromatic compounds and their polymers represented by formulas (2), (2-a), (2-b), (2-c), (2-d), (2-e), or (2-f) may be deuterium, cyano, or halogen. For example, in formula (2), ring A, ring B, ring C (rings A to C are aryl or heteroaryl rings), substituents for rings A to C, and X 3 and X 4 When the hydrogen atom is >NR or >C(-R)2, the hydrogen atom in R (=alkyl, cycloalkyl, aryl) can be substituted with deuterium, cyano, or halogen. Examples of substituted hydrogen atom in aryl or heteroaryl groups are deuterium, cyano, or halogen. The halogen is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, and more preferably fluorine or chlorine.

[0673] In addition, at least one of the groups consisting of aryl rings and heteroaryl rings in the chemical structures of polycyclic aromatic compounds and their polymers represented by formula (2), (2-a), (2-b), (2-c), (2-d), (2-e), or (2-f) can be condensed from at least one cycloalkane.

[0674] For example, aryl rings and heteroaryl rings in aryl rings and heteroaryl rings of rings A, B, C, a, b, and c; aryl (aryl moiety of aryl, diarylamino, arylheteroarylamino, diarylboryl, or aryloxy) and heteroaryl (heteroaryl, diarylamino, or heteroarylamino) moiety of the first and second substituents in rings A to C; aryl (same as described above) and heteroaryl (same as described above) of the first and second substituents for rings a, b, and c; and X. 1 X 2 At least one of the aryl (same as described) and heteroaryl (same as described) of R in >NR and >C(-R)2 can be condensed by at least one cycloalkane.

[0675] Preferably, the aryl ring and heteroaryl ring are the A ring, B ring, C ring, a ring, b ring, and c ring; the aryl group (aryl moiety of aryl, diarylamino, diarylboryl, or aryloxy group) and heteroaryl group (heteroaryl or heteroarylamino group) are the first substituents in the A to C rings; the aryl group (same as described above) and heteroaryl group (same as described above) are the first substituents for the a to c rings; and the group that becomes X 1 X 2 At least one of the aryl (same as described) and heteroaryl (same as described) of R in >NR and >C(-R)2 can be condensed by at least one cycloalkane.

[0676] More preferably, the aryl ring is one of the A, B, C, a, b, or c rings; the aryl group (aryl moiety of aryl or diarylamino) and heteroaryl group (heteroaryl moiety of heteroaryl) is the first substituent in the A to C rings; the aryl group (same as described above) and heteroaryl group (same as described above) is the first substituent for the a, b, or c rings; and the aryl group is the X... 1 X 2 At least one of the aryl groups of >NR and >C(-R)2 (as described above) can be condensed by at least one cycloalkane.

[0677] Preferably, the aryl ring is one of the A, B, C, a, b, or c rings; the aryl group (aryl moiety of aryl or diarylamino) is the first substituent in the A to C rings; the aryl group is the same as described above, which is the first substituent for the a, b, or c rings; and the aryl group is X. 1 X 2 At least one of the aryl groups of >NR and >C(-R)2 (as described above) can be condensed by at least one cycloalkane.

[0678] Examples of "cycloalkanes" include: cycloalkanes with 3 to 24 carbon atoms, cycloalkanes with 3 to 20 carbon atoms, cycloalkanes with 3 to 16 carbon atoms, cycloalkanes with 3 to 14 carbon atoms, cycloalkanes with 5 to 10 carbon atoms, cycloalkanes with 5 to 8 carbon atoms, cycloalkanes with 5 to 6 carbon atoms, and cycloalkanes with 5 carbon atoms.

[0679] Specific examples of cycloalkanes include: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo[1.0.1]butane, bicyclo[1.1.1]pentane, bicyclo[2.0.1]pentane, bicyclo[1.2.1]hexane, bicyclo[3.0.1]hexane, bicyclo[2.1.2]heptane, bicyclo[2.2.2]octane, adamantane, diadamantane, decahydronaphthalene and decahydroazine, and their alkyl (especially methyl) substituted derivatives, halogen (especially fluorine) substituted derivatives, and deuterium substituted derivatives, etc.

[0680] Among these, a structure in which at least one hydrogen atom is substituted in the α-carbon of the cycloalkane (the carbon atom adjacent to the carbon at the condensation site in a cycloalkyl group condensed with an aromatic or heteroaromatic ring), more preferably a structure in which two hydrogen atoms in the α-carbon are substituted, and even more preferably a structure in which a total of four hydrogen atoms in the two α-carbons are substituted. Examples of substituents include alkyl (especially methyl) derivatives with 1 to 5 carbon atoms, halogen (especially fluorine) derivatives, and deuterium derivatives.

[0681] It is particularly preferred to have a structure in which a partial structure represented by the following formula (B10) or formula (B11) is bonded to adjacent carbon atoms in an aryl ring or heteroaryl ring.

[0682] [Chemistry 143]

[0683]

[0684] In formulas (B10) and (B11), Me represents a methyl group. * indicates the bonding position, where the group represented by formula (B10) or (B11) is bonded to two adjacent elements on the ring of the bonded aryl or heteroaryl ring.

[0685] Examples of compounds with this structure include the following compounds.

[0686] [Chemistry 144]

[0687]

[0688] The number of cycloalkanes condensed on an aromatic or heteroaromatic ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, the following shows an example of one or more cycloalkanes condensed on a benzene ring (phenyl). The condensed cycloalkanes may also condense on each other, as in formulas (Cy-1-4) and (Cy-2-4). This is the same whether the condensed ring (group) is an aromatic or heteroaromatic ring other than a benzene ring (phenyl), or whether the condensed cycloalkanes are cycloalkanes other than cyclopentane or cyclohexane.

[0689] [Chemistry 145]

[0690]

[0691] At least one -CH2- in a cycloalkane may be substituted with -O-. For example, the following shows examples of one or more -CH2- in a cycloalkane condensed on a benzene ring (phenyl) being substituted with -O-. This is the same whether the condensed ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl), or whether the cycloalkane undergoing condensation is a cycloalkane other than cyclopentane or cyclohexane.

[0692] [Chemistry 146]

[0693]

[0694] At least one hydrogen atom in the cycloalkane may be substituted as a substituent, such as aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryl groups may be linked by a single bond or a linker), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano, or halogen, details of which can be found in the description of the first substituent. Among these substituents, alkyl (e.g., alkyl with 1 to 6 carbon atoms), cycloalkyl (e.g., cycloalkyl with 3 to 14 carbon atoms), halogen (e.g., fluorine), and deuterium are preferred. Furthermore, when the cycloalkyl group is substituted, a substituted form forming a spirocyclic structure may be achieved, as illustrated in the examples below.

[0695] [Chemistry 147]

[0696]

[0697] Other forms of cycloalkane condensation include: polycyclic aromatic compounds and their polymers represented by formulas (2), (2-a), (2-b), (2-c), (2-d), (2-e), or (2-f) having, for example, R being >NR, an aryl group condensed from a cycloalkane, a diarylamino group condensed from a cycloalkane (condensed to its aryl moiety), a carbazolyl group condensed from a cycloalkane (condensed to its benzene ring moiety), or a benzo[a]carbazolyl group condensed from a cycloalkane (condensed to its benzene ring moiety). Regarding "diarylamino," examples of groups described as "first substituents" can be cited.

[0698] Furthermore, as more specific examples, one can cite the R in polycyclic aromatic compounds and their polymers represented by formulas (2-a), (2-b), (2-c), (2-d), (2-e), or (2-f). 2 Examples include diarylamino groups condensed from cycloalkanes (condensed to their aryl moiety) or carbazole groups condensed from cycloalkanes (condensed to their benzene ring moiety).

[0699] As a more specific example of the polycyclic aromatic compounds represented by formula (2), compounds represented by the following formulas can be listed. In addition, in the following formulas, “Me” represents methyl, “tBu” represents tert-butyl, “iPr” represents isopropyl, “Ph” represents phenyl, “tAm” represents tertiary pentyl, and “D” represents deuterium.

[0700] [Chemistry 148]

[0701]

[0702] [Chemistry 149]

[0703]

[0704] [Chemistry 150]

[0705]

[0706] [Chemistry 151]

[0707]

[0708] [Chemistry 152]

[0709]

[0710] [Chemistry 153]

[0711]

[0712] [Chemistry 154]

[0713]

[0714] [Chemistry 155]

[0715]

[0716] [Chemistry 156]

[0717]

[0718] [Chemistry 157]

[0719]

[0720] [Chemistry 158]

[0721]

[0722] [Chemistry 159]

[0723]

[0724] [Chemistry 160]

[0725]

[0726] [Chemistry 161]

[0727]

[0728] [Chemistry 162]

[0729]

[0730] [Chemistry 163]

[0731]

[0732] [Chemistry 164]

[0733]

[0734] [Chemistry 165]

[0735]

[0736] [Chemistry 166]

[0737]

[0738] [Chemistry 167]

[0739]

[0740] [Chemistry 168]

[0741]

[0742] [Chemistry 169]

[0743]

[0744] [Chemistry 170]

[0745]

[0746] [Chemistry 171]

[0747]

[0748] [Chemistry 172]

[0749]

[0750] [Chemistry 173]

[0751]

[0752] [Chemistry 174]

[0753]

[0754] [Chemistry 175]

[0755]

[0756] [Chemistry 176]

[0757]

[0758] [Chemistry 177]

[0759]

[0760] [Chemistry 178]

[0761]

[0762] [Chemistry 179]

[0763]

[0764] [Chemistry 180]

[0765]

[0766] [Chemistry 181]

[0767]

[0768] [Chemistry 182]

[0769]

[0770] [Chemistry 183]

[0771]

[0772]

[0773] [Chemistry 184]

[0774]

[0775] [Chemistry 185]

[0776]

[0777] [Chemistry 186]

[0778]

[0779] [Chemistry 187]

[0780]

[0781] [Chemistry 188]

[0782]

[0783] [Chemistry 189]

[0784]

[0785] [Chemistry 190]

[0786]

[0787] 1-2-2. Method for manufacturing polycyclic aromatic compounds and their polymers represented by formula (2)

[0788] The polycyclic aromatic compounds and their polymers represented by formula (2) can be synthesized, for example, by the method disclosed in International Publication No. 2019 / 009052 as “Method for manufacturing polycyclic aromatic compounds and their polymers represented by formula (2)”.

[0789] 1-3. Emissive layer

[0790] The light-emitting layer can be a single layer or multiple layers, either of which is acceptable, and is formed from light-emitting layer materials (host material and dopant material). The host material can be a compound represented by formula (1), a combination of two or more compounds represented by formula (1), or a combination of a compound represented by formula (1) and a compound other than the compound represented by formula (1). The host material is preferably a compound represented by formula (1) or a combination of two or more compounds represented by formula (1). In addition, the dopant material can be a compound represented by formula (2), a combination of two or more compounds represented by formula (2), or a combination of a compound represented by formula (2) and a compound other than the compound represented by formula (2). The dopant material is preferably a compound represented by formula (2) or a combination of two or more compounds represented by formula (2).

[0791] The dopant material can be contained entirely within the host material or partially within the host material; either method is acceptable. As a doping method, it can be formed through co-evaporation with the host material, or it can be mixed with the host material beforehand and then evaporated simultaneously.

[0792] The amount of main material used varies depending on the type of main material, and can be determined by considering the characteristics of the main material. The preferred basis for the amount of main material used is 50% to 99.999% of the total mass of the material used in the light-emitting layer, more preferably 80% to 99.95% of the total mass, and even more preferably 90% to 99.9% of the total mass.

[0793] The amount of dopant material used varies depending on the type of dopant material, and can be determined in accordance with the characteristics of the dopant material. The preferred amount of dopant is 0.001% to 50% of the total mass of the material used in the luminescent layer, more preferably 0.05% to 20% by mass, and even more preferably 0.1% to 10% by mass. If it falls within this range, it is preferred, for example, in terms of preventing concentration quenching.

[0794] As host materials that can be used in conjunction with the compound represented by formula (1), examples include: pyrene and dibenzo[a], which have been known as luminescent organisms before. Diphenyl cyclopentadiene derivatives, bis(styrene) anthracene derivatives, bis(styrene) benzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzo[a]fluorene derivatives, etc.

[0795] Examples of dopant materials that can be used in conjunction with the compound represented by formula (2) include: fused ring derivatives such as anthracene or pyrene, bis(styrene) derivatives such as bis(styrene) anthracene derivatives or styrene benzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzo[a]fluorene derivatives, etc., which have been known as luminescent bodies before.

[0796] 2. Electron injection layer and electron transport layer of organic electroluminescent devices

[0797] The electron injection layer 107 efficiently injects electrons migrating from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 efficiently transports electrons injected from the cathode 108, or electrons injected from the cathode 108 via the electron injection layer 107, to the light-emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are formed by laminating or mixing one or more electron transport / injection materials, or by forming a mixture of electron transport / injection materials and a polymer binder.

[0798] The electron injection / transport layer is a layer responsible for the injection and transport of electrons from the cathode. Ideally, it should have high electron injection efficiency and efficient transport of the injected electrons. Therefore, materials with high electron affinity and high electron mobility, resulting in excellent stability and low likelihood of generating impurities that could become traps during manufacturing and use, are preferred. However, considering the balance between hole and electron transport, when the primary function is to efficiently prevent unrecombined holes from the anode from flowing to the cathode, even materials with lower electron transport capabilities can achieve the same effect of improving luminous efficiency as materials with high electron transport capabilities. Therefore, the electron injection / transport layer in this embodiment may also include the function of a layer that efficiently prevents hole migration.

[0799] The material (electron transport material) used to form the electron transport layer 106 or the electron injection layer 107 can be arbitrarily selected from compounds commonly used as electron transport compounds in photoconductive materials, and existing compounds used in the electron injection layer and electron transport layer of organic EL elements.

[0800] The materials used in the electron transport layer or electron injection layer are preferably compounds containing at least one of the following: compounds containing an aromatic ring or heteroaromatic ring comprising one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus; pyrrole derivatives and their fused-ring derivatives; and metal complexes with electron-accepting nitrogen. Specifically, examples include: fused-ring aromatic ring derivatives such as naphthalene and anthracene; styryl aromatic ring derivatives represented by 4,4'-bis(diphenylvinyl)biphenyl; violet ketone derivatives; coumarin derivatives; naphthalenedicarboximide derivatives; quinone derivatives such as anthraquinone or biphenylquinone; phosphine oxide derivatives; aryl nitrile derivatives; and indole derivatives. Examples of metal complexes with electron-accepting nitrogen include: hydroxyazole complexes such as hydroxyphenyloxazole complexes; methylimine complexes; cycloheptatrienolone metal complexes; flavonol metal complexes; and benzoquinoline metal complexes. These materials can be used alone or in combination with different materials.

[0801] In addition, specific examples of other electron-transfer compounds include: borane derivatives, pyridine derivatives, naphthalene derivatives, fluoranthene derivatives, BO series derivatives, anthracene derivatives, benzo[a]fluorene derivatives, phenanthroline derivatives, violacetone derivatives, coumarin derivatives, naphthalenedicarboximide derivatives, anthraquinone derivatives, biphenylquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (1,3-bis[(4-tert-butylphenyl)1,3,4-oxadiazolyl]benzene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl-1,3,4-triazole, etc.), thiadiazole derivatives, metal complexes of 8-hydroxyquinoline derivatives, hydroxyquinoline-based metal complexes, quinoxoline derivatives, polymers of quinoxoline derivatives, indole (benzazole) compounds, gallium complexes, pyridine... Zyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (2,2'-bis(benzo[h]quinoline-2-yl)-9,9'-spirodifluorene, etc.), imidazopyridine derivatives, benzimidazole derivatives (tris(N-phenylbenzimidazole-2-yl)benzene, etc.), benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(4'-(2,2':6'2”-terpyridyl))benzene, naphthidine derivatives (bis(1-naphthyl)-4-(1,8-naphthidyl-2-yl)phenylphosphine oxide, etc.), aldehyde azide derivatives, pyrimidine derivatives, aryl nitrile derivatives, indole derivatives, phosphorus oxide derivatives, bisstyryl derivatives, thiophene derivatives, and zoline derivatives, etc.

[0802] In addition, metal complexes with electron-accepting nitrogen can also be used, such as: hydroxyquinoline metal complexes or hydroxyphenyloxazole complexes, methylimine complexes, cycloheptatrienolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0803] The material can be used alone or in combination with different materials.

[0804] The preferred materials are borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzo[a]fluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, aryl nitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, hydroxyquinoline-based metal complexes, thiazole derivatives, benzo[a]thiazole derivatives, thiophene derivatives, and azoline derivatives.

[0805] <Boronane Derivatives>

[0806] Borane derivatives, for example, are compounds represented by the following formula (ETM-1), which are disclosed in detail in Japanese Patent Application Publication No. 2007-27587.

[0807] [Chemistry 191]

[0808]

[0809] In formula (ETM-1), R 11 and R 12 R is independently one of hydrogen, alkyl, cycloalkyl, substituted aryl, substituted silyl, substituted nitrogen-containing heterocycle or cyano. 13 ~R 16 Each of the following groups is independently a substituted alkyl, substituted cycloalkyl, or substituted aryl group; X is a substituted arylene group; Y is a substituted aryl group with 16 or fewer carbon atoms, a substituted boryl group, or a substituted carbazole group; and n is independently an integer from 0 to 3. Examples of substituents in the "substituted" or "substituted" cases include aryl, heteroaryl, alkyl, or cycloalkyl groups.

[0810] Among the compounds represented by formula (ETM-1), the compounds represented by formula (ETM-1-1) or formula (ETM-1-2) are preferred.

[0811] [Chemistry 192]

[0812]

[0813] In formula (ETM-1-1), R 11 and R 12R is independently one of hydrogen, alkyl, cycloalkyl, substituted aryl, substituted silyl, substituted nitrogen-containing heterocycle or cyano. 13 ~R 16 R is independently a substituted alkyl, a substituted cycloalkyl, or a substituted aryl group. 21 and R 22 Each of the following is independently one of hydrogen, alkyl, cycloalkyl, substituted aryl, substituted silyl, substituted nitrogen-containing heterocycle, or cyano, X 1 The substituent is a arylene group with 20 or fewer carbon atoms that can be substituted, where n is an integer from 0 to 3, and m is an integer from 0 to 4. Examples of substituents that can be substituted or substituted include aryl, heteroaryl, alkyl, or cycloalkyl groups.

[0814] [Chemistry 193]

[0815]

[0816] In formula (ETM-1-2), R 11 and R 12 R is independently one of hydrogen, alkyl, cycloalkyl, substituted aryl, substituted silyl, substituted nitrogen-containing heterocycle or cyano. 13 ~R 16 Each of the following is independently a substituted alkyl, a substituted cycloalkyl, or a substituted aryl group, X 1 It is an arylene group with 20 or fewer carbon atoms that can be substituted, and n is an integer from 0 to 3 independently. In addition, examples of substituents in the case of "substitutable" or "substituted" include: aryl, heteroaryl, alkyl or cycloalkyl, etc.

[0817] As X 1 Specific examples can be listed as the divalent base represented by any of the following equations (X-1) to (X-9).

[0818] [Chemistry 194]

[0819]

[0820] (In each formula, R) a Each is independently an alkyl, cycloalkyl, or substituted phenyl group (* indicates the bond position).

[0821] Specific examples of the borane derivatives include the following compounds.

[0822] [Chemistry 195]

[0823]

[0824] The borane derivatives can be manufactured using existing raw materials and existing synthetic methods.

[0825] <Pyridine Derivatives>

[0826] The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), preferably a compound represented by formula (ETM-2-1) or formula (ETM-2-2).

[0827] [Chemistry 196]

[0828]

[0829] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzo[a]fluorene ring, finadene ring, phenanthrene ring, or triphenylene ring), and n is an integer from 1 to 4.

[0830] In equation (ETM-2-1), R 11 ~R 18 Each of the following can be independently hydrogen, alkyl (preferably alkyl with 1 to 24 carbons), cycloalkyl (preferably cycloalkyl with 3 to 12 carbons) or aryl (preferably aryl with 6 to 30 carbons).

[0831] In equation (ETM-2-2), R 11 and R 12 Each of the following is independently hydrogen, alkyl (preferably alkyl with 1 to 24 carbons), cycloalkyl (preferably cycloalkyl with 3 to 12 carbons), or aryl (preferably aryl with 6 to 30 carbons), R 11 and R 12 They can bond together to form a ring.

[0832] In each formula, the "pyridine substituent" is any one of the following formulas (Py-1) to (Py-15) (where * indicates the bonding position), and the pyridine substituent may be independently substituted by an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms. Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, with methyl being preferred. Furthermore, the pyridine substituent may be bonded to the φ, anthracene ring, or fluorene ring in each formula via a phenylene or naphthylene group.

[0833] [Chemistry 197]

[0834]

[0835] The pyridine substituents are any of formulas (Py-1) to (Py-15), among which, preferably any of formulas (Py-21) to (Py-44) (where * indicates the bond position).

[0836] [Chemistry 198]

[0837]

[0838] At least one hydrogen atom in each pyridine derivative may be substituted with deuterium. In addition, one of the two “pyridine substituents” in formula (ETM-2-1) and formula (ETM-2-2) may be substituted with aryl.

[0839] As R 11 ~R 18 The term "alkyl" can be either straight-chain or branched, for example, straight-chain alkyl with 1 to 24 carbon atoms or branched alkyl with 3 to 24 carbon atoms. Preferred "alkyl" is an alkyl with 1 to 18 carbon atoms (branched alkyl with 3 to 18 carbon atoms). More preferably, an alkyl with 1 to 12 carbon atoms (branched alkyl with 3 to 12 carbon atoms). Even more preferably, an alkyl with 1 to 6 carbon atoms (branched alkyl with 3 to 6 carbon atoms). Particularly preferred "alkyl" is an alkyl with 1 to 4 carbon atoms (branched alkyl with 3 to 4 carbon atoms).

[0840] Specific examples of "alkyl groups" include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc.

[0841] The description of the alkyl group that has 1 to 4 carbon atoms and is used to substitute for the pyridine substituent can be cited.

[0842] As R 11 ~R 18 The term "cycloalkyl" can be exemplified by cycloalkyl groups having 3 to 12 carbon atoms. Preferably, the "cycloalkyl" is a cycloalkyl group having 3 to 10 carbon atoms. More preferably, the "cycloalkyl" is a cycloalkyl group having 3 to 8 carbon atoms. Even more preferably, the "cycloalkyl" is a cycloalkyl group having 3 to 6 carbon atoms.

[0843] Specific examples of "cycloalkyl groups" include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl, etc.

[0844] As R 11 ~R 18The "aryl" in the text is preferably an aryl group with 6 to 30 carbon atoms, more preferably an aryl group with 6 to 18 carbon atoms, and even more preferably an aryl group with 6 to 14 carbon atoms, and particularly preferably an aryl group with 6 to 12 carbon atoms.

[0845] Specific examples of "aryl groups with 6 to 30 carbon atoms" include: phenyl as a monocyclic aryl group; (1-, 2-)naphthyl as a condensed bicyclic aryl group; acenaphthene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenaten-(1-, 2-)yl, and (1-, 2-, 3-, 4-, 9-)phenanthyl as condensed tricyclic aryl groups; triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, and tetraphenyl-(1-, 2-, 5-)yl as condensed tetracyclic aryl groups; and perylene-(1-, 2-, 3-)yl and pentaphenyl-(1-, 2-, 5-, 6-)yl as condensed pentacyclic aryl groups.

[0846] Preferred aryl groups with 6 to 30 carbon atoms include phenyl, naphthyl, phenanthrene, etc. The compounds may be phenyl, 1-naphthyl, 2-naphthyl or phenanthrene, and are particularly preferably phenyl, 1-naphthyl or 2-naphthyl.

[0847] R in equation (ETM-2-2) 11 and R 12 It can bond to form rings, resulting in the formation of cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, or indene, etc., on the five-membered ring of the fluorene skeleton.

[0848] Specific examples of the pyridine derivatives include the following compounds.

[0849] [Chemistry 199]

[0850]

[0851] The pyridine derivative can be manufactured using existing raw materials and existing synthetic methods.

[0852] <Fluoranthracene derivatives>

[0853] Fluoranthracene derivatives are, for example, compounds represented by the following formula (ETM-3), which are disclosed in detail in International Publication No. 2010 / 134352.

[0854] [Chemistry 200]

[0855]

[0856] In formula (ETM-3), X 12 ~X 21This refers to hydrogen, halogen, straight-chain, branched or cyclic alkyl, straight-chain, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Here, examples of substituents in the case of substitution include aryl, heteroaryl, alkyl, or cycloalkyl.

[0857] Specific examples of the fluoranthene derivatives include the following compounds.

[0858] [Chemical Engineering 201]

[0859]

[0860] <BO-series derivatives>

[0861] BO derivatives are, for example, polycyclic aromatic compounds represented by the following formula (ETM-4) or polymers of polycyclic aromatic compounds having a plurality of structures represented by the following formula (ETM-4).

[0862] [Chemical Engineering 202]

[0863]

[0864] R 61 ~R 71 Each of the following is independently hydrogen, aryl, heteroaryl, diarylamino, diherylamino, arylherylamino, alkyl, cycloalkyl, alkoxy, or aryloxy, wherein at least one hydrogen atom may be substituted by aryl, heteroaryl, alkyl, or cycloalkyl.

[0865] Additionally, R 61 ~R 71 The adjacent groups in the ring can be bonded to each other and together with the a ring, b ring or c ring to form an aryl ring or a heteroaryl ring. At least one hydrogen in the formed ring can be replaced by an aryl, heteroaryl, diarylamino, diarylamino, arylhexylamino, alkyl, cycloalkyl, alkoxy or aryloxy group. At least one hydrogen in the ring can be replaced by an aryl, heteroaryl, alkyl or cycloalkyl group.

[0866] In addition, at least one hydrogen atom in the compound or structure represented by formula (ETM-4) may be substituted with halogen or deuterium.

[0867] For an explanation of the morphology of the substituents or rings in formula (ETM-4), refer to the description of the polycyclic aromatic compounds represented by formula (1) or formula (2).

[0868] Specific examples of the BO-based derivatives include the following compounds.

[0869] [Chemical Engineering 203]

[0870]

[0871] The BO-based derivatives can be manufactured using existing raw materials and existing synthetic methods.

[0872] <Anthracene derivatives>

[0873] One example of anthracene derivatives is a compound represented by the following formula (ETM-5).

[0874] [Chemical 204]

[0875]

[0876] Ar 1 Each of these can be independently a single bond, a divalent benzene, naphthalene, anthracene, fluorene, or finasteride.

[0877] Ar 2 Each aryl group is independently composed of 6 to 20 carbon atoms, preferably 6 to 16 carbon atoms, more preferably 6 to 12 carbon atoms, and particularly preferably 6 to 10 carbon atoms. Specific examples of "aryl groups with 6 to 20 carbon atoms" include: phenyl, (o-, m-, p-)tolyl, (2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5-)xylyl, mesityleneyl (2,4,6-trimethylphenyl), and (o-, m-, p-)cumenel as monocyclic aryl groups; (2-, 3-, 4-)biphenyl as bicyclic aryl groups; (1-, 2-)naphthyl as condensed bicyclic aryl groups; and terphenyl as tricyclic aryl groups (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m ... 3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl); anthracene-(1-, 2-, 9-)yl, acenaphthene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenaten-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthrene- as condensed tricyclic aryl groups; triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, benzotetraphenyl-(1-, 2-, 5-)yl as condensed tetracyclic aryl groups; perylene-(1-, 2-, 3-)yl as condensed pentacyclic aryl groups, etc. Specific examples of "aryl groups with 6 to 10 carbon atoms" include: phenyl, biphenyl, naphthyl, terphenyl, anthracene, acenaphthene, fluorenyl, phenatenyl, phenylene, pyrene, tetraphenyl, perylene, etc.

[0878] R 1 ~R 4Each of the following is independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

[0879] Regarding R 1 ~R 4 The alkyl group having 1 to 6 carbon atoms can be either straight-chain or branched. That is, it can be a straight-chain alkyl group having 1 to 6 carbon atoms or a branched alkyl group having 3 to 6 carbon atoms. More preferably, it can be an alkyl group having 1 to 4 carbon atoms (or a branched alkyl group having 3 to 4 carbon atoms). Specific examples include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, or 2-ethylbutyl, etc., preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, more preferably methyl, ethyl, or tert-butyl.

[0880] As R 1 ~R 4 Specific examples of cycloalkyl groups having 3 to 6 carbon atoms include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl, etc.

[0881] Regarding R 1 ~R 4 The aryl group having 6 to 20 carbon atoms is preferably an aryl group having 6 to 16 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms. As a specific example of "aryl group having 6 to 20 carbon atoms", Ar... 2 Specific examples of "aryl group having 6 to 20 carbon atoms". Preferred "aryl group having 6 to 20 carbon atoms" is phenyl, biphenyl, terphenyl or naphthyl, more preferably phenyl, biphenyl, 1-naphthyl, 2-naphthyl or meta-terphenyl-5'-yl, further preferably phenyl, biphenyl, 1-naphthyl or 2-naphthyl, and most preferably phenyl.

[0882] Specific examples of these anthracene derivatives include the following compounds.

[0883] [Chemical Engineering 205]

[0884]

[0885] These anthracene derivatives can be manufactured using existing raw materials and existing synthetic methods.

[0886] <Benzofluorene derivatives>

[0887] Benzo[a]fluorene derivatives are, for example, compounds represented by the following formula (ETM-6).

[0888] [Chemical Engineering 206]

[0889]

[0890] Ar 1 Each is an aryl group, independently having 6 to 20 carbon atoms, and can be referenced in Ar of formula (ETM-5). 2 The same description applies to "aryl group with 6 to 20 carbon atoms". Preferably, it is an aryl group with 6 to 16 carbon atoms, more preferably an aryl group with 6 to 12 carbon atoms, and particularly preferably an aryl group with 6 to 10 carbon atoms. Specific examples include: phenyl, biphenyl, naphthyl, terphenyl, anthracene, acenaphthene, fluorenyl, phenatenyl, phenylene, pyrene, tetraphenyl, perylene, etc.

[0891] Ar 2 Each of the two Ar groups is independently hydrogen, alkyl (preferably alkyl with 1 to 24 carbons), cycloalkyl (preferably cycloalkyl with 3 to 12 carbons), or aryl (preferably aryl with 6 to 30 carbons). 2 They can bond together to form a ring.

[0892] As Ar 2 The term "alkyl" can be either straight-chain or branched, for example, straight-chain alkyl with 1 to 24 carbon atoms or branched alkyl with 3 to 24 carbon atoms. Preferred "alkyl" is an alkyl with 1 to 18 carbon atoms (branched alkyl with 3 to 18 carbon atoms). More preferably, an alkyl with 1 to 12 carbon atoms (branched alkyl with 3 to 12 carbon atoms). Further preferred "alkyl" is an alkyl with 1 to 6 carbon atoms (branched alkyl with 3 to 6 carbon atoms). Particularly preferred "alkyl" is an alkyl with 1 to 4 carbon atoms (branched alkyl with 3 to 4 carbon atoms). Specific examples of "alkyl" include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, etc.

[0893] As Ar 2 The term "cycloalkyl" can be exemplified by cycloalkyl groups having 3 to 12 carbon atoms. Preferably, the "cycloalkyl" is a cycloalkyl group having 3 to 10 carbon atoms. More preferably, the "cycloalkyl" is a cycloalkyl group having 3 to 8 carbon atoms. Even more preferably, the "cycloalkyl" is a cycloalkyl group having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl.

[0894] As Ar 2 The "aryl" in the text is preferably an aryl group with 6 to 30 carbon atoms, more preferably an aryl group with 6 to 18 carbon atoms, and even more preferably an aryl group with 6 to 14 carbon atoms, and particularly preferably an aryl group with 6 to 12 carbon atoms.

[0895] Specific examples of "aryl groups with 6 to 30 carbon atoms" include: phenyl, naphthyl, acenaphthel, fluorenyl, phenatenyl, phenylene, pyrene, tetraphenyl, peryl, pentaphenyl, etc.

[0896] Two Ar 2 It can bond to form rings, resulting in the formation of cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, or indene, etc., on the five-membered ring of the fluorene skeleton.

[0897] Specific examples of the benzo[a]fluorene derivatives include the following compounds.

[0898] [Chemical 207]

[0899]

[0900] The benzo[a]fluorene derivatives can be manufactured using existing raw materials and existing synthetic methods.

[0901] <phosphine oxide derivatives>

[0902] Phosphine oxide derivatives are, for example, compounds represented by the following formula (ETM-7-1). Details are also described in International Publication Nos. 2013 / 079217 and 2013 / 079678.

[0903] [Chemical Engineering 208]

[0904]

[0905] R 5 It can be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 16 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 5 to 20 carbon atoms.

[0906] R 6 CN, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 16 carbon atoms, heteroalkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 5 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, or aryloxy groups having 6 to 20 carbon atoms.

[0907] R 7 and R 8 R is independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a heteroaryl group having 5 to 20 carbon atoms. 9 It is oxygen or sulfur.

[0908] j is 0 or 1, k is 0 or 1, r is an integer from 0 to 4, and q is an integer from 1 to 3.

[0909] Here, examples of substituents in the case of substitution include: aryl, heteroaryl, alkyl, or cycloalkyl.

[0910] Phosphine oxide derivatives may be, for example, compounds represented by the following formula (ETM-7-2).

[0911] [Chemical Engineering 209]

[0912]

[0913] R 1 ~R 3 They may be the same or different, and are selected from hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, cycloalkylthio, aryl ether, aryl thioether, aryl, heterocyclic, halogen, cyano, formyl, carbonyl, carboxyl, amino, nitro, silyl, and fused rings formed between them and adjacent substituents.

[0914] Ar 1 They can be the same or different, and are either aryl or heteroaryl. Ar 2 They can be the same or different, and can be aryl or heteroaryl. Among them, Ar 1 and Ar 2 At least one of them has a substituent, or forms a fused ring with an adjacent substituent. n is an integer from 0 to 3; when n is 0, there is no unsaturated structural part; when n is 3, there is no R. 1 .

[0915] Among these substituents, the term alkyl refers to, for example, saturated aliphatic hydrocarbon groups such as methyl, ethyl, propyl, and butyl. The alkyl group may be unsubstituted or substituted. There are no particular limitations on the substituents used in substituted cases; examples include alkyl, aryl, and heterocyclic groups, and this aspect will be consistent throughout the following description. Furthermore, there is no particular limitation on the number of carbon atoms in the alkyl group; it is generally in the range of 1 to 20, considering ease of acquisition and cost.

[0916] Furthermore, the term "cycloalkyl" can refer to saturated alicyclic hydrocarbon groups such as cyclopropyl, cyclohexyl, norbornyl, and adamantyl, and the cycloalkyl group may be unsubstituted or substituted. The number of carbon atoms in the alkyl moiety is not particularly limited, and is typically in the range of 3 to 20.

[0917] Furthermore, the term "aralkyl" refers to aromatic hydrocarbon groups such as benzyl and phenylethyl, which are separated by an aliphatic hydrocarbon. Both aliphatic and aromatic hydrocarbons can be unsubstituted or substituted. The number of carbon atoms in the aliphatic moiety is not particularly limited, and is usually in the range of 1 to 20.

[0918] Furthermore, the term "alkenyl" refers to unsaturated aliphatic hydrocarbon groups containing double bonds, such as vinyl, allyl, and butadienyl. The alkenyl group may be unsubstituted or substituted. The number of carbon atoms in the alkenyl group is not particularly limited, but is typically in the range of 2 to 20.

[0919] In addition, the term "cycloalkenyl" can refer to, for example, unsaturated alicyclic hydrocarbon groups containing double bonds such as cyclopentenyl, cyclopentadienyl, and cyclohexene, and the cycloalkenyl group may be unsubstituted or substituted.

[0920] Furthermore, the term "alkynyl" refers to, for example, an acetylenic group or other unsaturated aliphatic hydrocarbon group containing a triple bond, which may be unsubstituted or substituted. The number of carbon atoms in the alkynyl group is not particularly limited, but is typically in the range of 2 to 20.

[0921] In addition, the term alkoxy refers to an aliphatic hydrocarbon group, such as a methoxy group, separated by an ether bond. The aliphatic hydrocarbon group can be unsubstituted or substituted. The number of carbon atoms in an alkoxy group is not particularly limited, but is typically in the range of 1 to 20.

[0922] In addition, the so-called alkathioyl group is a group in which the oxygen atom of the ether bond of an alkoxy group is replaced by a sulfur atom.

[0923] In addition, the so-called cycloalkanethio group is a group in which the oxygen atom of the ether bond of the cycloalkoxy group is replaced by a sulfur atom.

[0924] Furthermore, the term "aryl ether" refers to aromatic hydrocarbon groups such as phenoxy groups, which are separated by an ether bond. These aromatic hydrocarbon groups can be unsubstituted or substituted. There is no particular limitation on the number of carbon atoms in an aryl ether group, which is typically in the range of 6 to 40.

[0925] In addition, the so-called arylthioether group is a group in which the oxygen atom of the ether bond is replaced by a sulfur atom.

[0926] In addition, the term "aryl" can refer to aromatic hydrocarbon groups such as phenyl, naphthyl, biphenyl, phenanthryl, terphenyl, and pyrene. Aryl groups can be unsubstituted or substituted. The number of carbon atoms in an aryl group is not particularly limited, typically ranging from 6 to 40.

[0927] Furthermore, the term "heterocyclic group" refers to cyclic groups with atoms other than carbon, such as furanyl, thiophene, oxazolyl, pyridyl, quinolinyl, and carbazole. These heterocyclic groups may be unsubstituted or substituted. The number of carbon atoms in the heterocyclic group is not particularly limited, but is typically in the range of 2 to 30.

[0928] The term halogen refers to fluorine, chlorine, bromine, and iodine.

[0929] The formyl, carbonyl, and amino groups may also contain groups substituted by aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles, etc.

[0930] In addition, aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and heterocyclic hydrocarbons can be unsubstituted or substituted.

[0931] The term silyl group refers to silicon compounds such as trimethylsilyl, which may be unsubstituted or substituted. The number of carbon atoms in the silyl group is not particularly limited, typically ranging from 3 to 20. Additionally, the number of silicon atoms is typically from 1 to 6.

[0932] The so-called fused ring formed between the adjacent substituent, for example, in Ar 1 With R 2 Ar 1 With R 3 Ar 2 With R 2 Ar 2 With R 3 R 2 With R 3 Ar 1 with Ar 2 Conjugate or non-conjugate condensed rings formed between them. Here, when n is 1, the two R... 1 They can form conjugated or non-conjugated fused rings. These fused rings may also contain nitrogen, oxygen, and sulfur atoms in their internal structure, and may further condense with other rings.

[0933] Specific examples of the phosphine oxide derivatives include the following compounds.

[0934] [Chemical 210]

[0935]

[0936] The phosphine oxide derivatives can be manufactured using existing raw materials and existing synthetic methods.

[0937] <Pyrimidine Derivatives>

[0938] The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), preferably a compound represented by the following formula (ETM-8-1). Further details are described in International Publication No. 2011 / 021689.

[0939] [Chemistry 211]

[0940]

[0941] Ar is independently a substituted aryl group or a substituted heteroaryl group. n is an integer from 1 to 4, preferably an integer from 1 to 3, and more preferably 2 or 3.

[0942] The "aryl" as "substitutable aryl" can be exemplified by aryl groups having 6 to 30 carbon atoms, preferably aryl groups having 6 to 24 carbon atoms, more preferably aryl groups having 6 to 20 carbon atoms, and even more preferably aryl groups having 6 to 12 carbon atoms.

[0943] Specific examples of "aryl" groups include: phenyl as a monocyclic aryl group; (2-, 3-, 4-)biphenyl as a dicyclic aryl group; (1-, 2-)naphthyl as a condensed dicyclic aryl group; terphenyl as a tricyclic aryl group (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl); and condensed tricyclic aryl groups. Acenatho-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenaten-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthyl; tetraphenyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-tetraphenyl) as tetracyclic aryl groups; triphenyl-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, and tetraphenyl-(1-, 2-, 5-)yl as condensed tetracyclic aryl groups; perylene-(1-, 2-, 3-)yl and pentaphenyl-(1-, 2-, 5-, 6-)yl as condensed pentacyclic aryl groups, etc.

[0944] The term "heteroaryl" as "substitutable heteroaryl" can include, for example, heteroaryl groups with 2 to 30 carbon atoms, preferably heteroaryl groups with 2 to 25 carbon atoms, more preferably heteroaryl groups with 2 to 20 carbon atoms, and even more preferably heteroaryl groups with 2 to 15 carbon atoms, and particularly preferably heteroaryl groups with 2 to 10 carbon atoms. Furthermore, heterocycles containing one to five heteroatoms selected from oxygen, sulfur, and nitrogen as ring-forming atoms, in addition to carbon, can be cited as examples.

[0945] Specific heteroaryl groups include, for example: furanyl, thiophene, pyrrole, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazole, pyrazolyl, oxadiazolyl, furazolyl, thiazolyl, triazolyl, tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thiophene, indolyl, isoindolyl, 1H-indolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinolinyl, quinazolinyl, quinoxolinyl, phthalazinyl, naphridinyl, purine, pteridinyl, carbazolyl, acridineyl, phenoxazinyl, phenthiazinyl, phenoxazinyl, thiazothiazyl, thiazothiazyl, indazinyl, etc.

[0946] In addition, the aryl and heteroaryl groups may be substituted, for example, by the aryl or heteroaryl groups respectively.

[0947] Specific examples of the pyrimidine derivatives include the following compounds.

[0948] [Chemistry 212]

[0949]

[0950] The pyrimidine derivatives can be manufactured using existing raw materials and existing synthetic methods.

[0951] <Aryl nitrile derivatives>

[0952] Aryl nitrile derivatives include, for example, compounds represented by the following formula (ETM-9), or polymers thereof formed by multiple such compounds linked by single bonds. Details are described in U.S. Patent Application Publication No. 2014 / 0197386.

[0953] [Chemistry 213]

[0954]

[0955] From the perspective of rapid electron transport, Ar ni Preferably, Ar has a higher carbon number, which is desirable from the perspective of high T1. ni Preferably, it has a low carbon number. Specifically, when used as a layer adjacent to the light-emitting layer, it is preferable to have a high T1 and Ar. ni The aryl group has 6 to 20 carbon atoms, preferably 6 to 14 carbon atoms, and more preferably 6 to 10 carbon atoms. Furthermore, regarding the number of nitrile group substitutions n, from the viewpoint of high T1, it is preferable to have more, and from the viewpoint of high S1, it is preferable to have fewer. Specifically, the number of nitrile group substitutions n is an integer from 1 to 4, preferably an integer from 1 to 3, more preferably an integer from 1 to 2, and even more preferably 1.

[0956] Ar is independently a substituted aryl or a substituted heteroaryl. From the viewpoint of high S1 and high T1, a donor heteroaryl is preferred, and since it serves as an electron transport layer, a small number of donor heteroaryl groups is preferred. From the viewpoint of charge transport, an aryl or heteroaryl group with a large number of carbon atoms is preferred, and a large number of substituents is preferred. Specifically, the number of substitutions m of Ar is an integer from 1 to 4, preferably an integer from 1 to 3, and more preferably 1 to 2.

[0957] The "aryl" as "substitutable aryl" can be exemplified by aryl groups having 6 to 30 carbon atoms, preferably aryl groups having 6 to 24 carbon atoms, more preferably aryl groups having 6 to 20 carbon atoms, and even more preferably aryl groups having 6 to 12 carbon atoms.

[0958] Specific examples of "aryl" groups include: phenyl as a monocyclic aryl group; (2-, 3-, 4-)biphenyl as a dicyclic aryl group; (1-, 2-)naphthyl as a condensed dicyclic aryl group; terphenyl as a tricyclic aryl group (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl); and condensed tricyclic aryl groups. Acenatho-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenaten-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthyl, tetraphenyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-tetraphenyl) as tetracyclic aryl, triphenyl-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, and tetraphenyl-(1-, 2-, 5-)yl as condensed tetracyclic aryl, and perylene-(1-, 2-, 3-)yl and pentaphenyl-(1-, 2-, 5-, 6-)yl as condensed pentacyclic aryl, etc.

[0959] The term "heteroaryl" as "substitutable heteroaryl" can include, for example, heteroaryl groups with 2 to 30 carbon atoms, preferably heteroaryl groups with 2 to 25 carbon atoms, more preferably heteroaryl groups with 2 to 20 carbon atoms, and even more preferably heteroaryl groups with 2 to 15 carbon atoms, and particularly preferably heteroaryl groups with 2 to 10 carbon atoms. Furthermore, heterocycles containing one to five heteroatoms selected from oxygen, sulfur, and nitrogen as ring-forming atoms, in addition to carbon, can be cited as examples.

[0960] Specific heteroaryl groups include, for example: furanyl, thiophene, pyrrole, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazole, pyrazolyl, oxadiazolyl, furazolyl, thiazolyl, triazolyl, tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thiophene, indolyl, isoindolyl, 1H-indolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinolinyl, quinazolinyl, quinoxolinyl, phthalazinyl, naphridinyl, purine, pteridinyl, carbazolyl, acridineyl, phenoxazinyl, phenthiazinyl, phenoxazinyl, thiazothiazyl, thiazothiazyl, indazinyl, etc.

[0961] In addition, the aryl and heteroaryl groups may be substituted, for example, by the aryl or heteroaryl groups respectively.

[0962] The aryl nitrile derivative can be a polymer of the compound represented by formula (ETM-9) formed by multiple bonds such as single bonds. In this case, in addition to single bonds, aryl rings (preferably polyvalent benzene rings, naphthyl rings, anthracene rings, fluorene rings, benzo[a]fluorene rings, phenanthracene rings, or triphenylene rings) can also be used for bonding.

[0963] Specific examples of the aryl nitrile derivatives include the following compounds.

[0964] [Chemistry 214]

[0965]

[0966] The aryl nitrile derivatives can be manufactured using existing raw materials and existing synthetic methods.

[0967] <Triazine derivatives>

[0968] Triazine derivatives are, for example, compounds represented by the following formula (ETM-10), preferably compounds represented by the following formula (ETM-10-1). Details are described in U.S. Patent Application Publication No. 2011 / 0156013.

[0969] [Chemical 215]

[0970]

[0971] Ar can be independently a substituted aryl group or a substituted heteroaryl group. n is an integer from 1 to 3, preferably 2 or 3.

[0972] The "aryl" as "substitutable aryl" can be exemplified by aryl groups having 6 to 30 carbon atoms, preferably aryl groups having 6 to 24 carbon atoms, more preferably aryl groups having 6 to 20 carbon atoms, and even more preferably aryl groups having 6 to 12 carbon atoms.

[0973] Specific examples of "aryl" groups include: phenyl as a monocyclic aryl group; (2-, 3-, 4-)biphenyl as a dicyclic aryl group; (1-, 2-)naphthyl as a condensed dicyclic aryl group; terphenyl as a tricyclic aryl group (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl); and condensed tricyclic aryl groups. Acenatho-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenaten-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthyl, tetraphenyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-tetraphenyl) as tetracyclic aryl, triphenyl-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, and tetraphenyl-(1-, 2-, 5-)yl as condensed tetracyclic aryl, and perylene-(1-, 2-, 3-)yl and pentaphenyl-(1-, 2-, 5-, 6-)yl as condensed pentacyclic aryl, etc.

[0974] The term "heteroaryl" as "substitutable heteroaryl" can include, for example, heteroaryl groups with 2 to 30 carbon atoms, preferably heteroaryl groups with 2 to 25 carbon atoms, more preferably heteroaryl groups with 2 to 20 carbon atoms, and even more preferably heteroaryl groups with 2 to 15 carbon atoms, and particularly preferably heteroaryl groups with 2 to 10 carbon atoms. Furthermore, heterocycles containing one to five heteroatoms selected from oxygen, sulfur, and nitrogen as ring-forming atoms, in addition to carbon, can be cited as examples.

[0975] Specific heteroaryl groups include, for example: furanyl, thiophene, pyrrole, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazole, pyrazolyl, oxadiazolyl, furazolyl, thiazolyl, triazolyl, tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thiophene, indolyl, isoindolyl, 1H-indolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinolinyl, quinazolinyl, quinoxolinyl, phthalazinyl, naphridinyl, purine, pteridinyl, carbazolyl, acridineyl, phenoxazinyl, phenthiazinyl, phenoxazinyl, thiazothiazyl, thiazothiazyl, indazinyl, etc.

[0976] In addition, the aryl and heteroaryl groups may be substituted, for example, by the aryl or heteroaryl groups respectively.

[0977] Specific examples of the triazine derivatives include the following compounds.

[0978] [Chemistry 216]

[0979]

[0980] The triazine derivative can be manufactured using existing raw materials and existing synthetic methods.

[0981] <Benzimazole derivatives>

[0982] Benzimidazole derivatives are, for example, compounds represented by the following formula (ETM-11).

[0983] [Chemistry 217]

[0984] φ-(benzimidazole substituent)n (ETM-11)

[0985] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthyl ring, anthracene ring, fluorene ring, benzo[a]fluorene ring, finadene ring, phenanthrene ring, or triphenylene ring), n is an integer from 1 to 4, "benzimidazole substituent" is a substituent in which the pyridinium group in the "pyridine substituent" of formula (ETM-2), formula (ETM-2-1) and formula (ETM-2-2) is replaced with a benzimidazole group, and at least one hydrogen in the benzimidazole derivative may be replaced by deuterium.

[0986] [Chemistry 218]

[0987] * indicates the location of the bond.

[0988] R in the benzimidazole group 11 It is hydrogen, an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an aryl group having 6 to 30 carbon atoms, and R in formulas (ETM-2-1) and (ETM-2-2) can be referenced. 11 Explanation.

[0989] φ is preferably an anthracene ring or a fluorene ring, the structure of which can be described by referring to the description in formula (ETM-2-1) or formula (ETM-2-2), where R in each formula 11 ~R 18 The description in ETM-2-1 or ETM-2-2 can be referenced. Furthermore, ETM-2-1 or ETM-2-2 is described in the form of two pyridine substituents, but when they are replaced with benzimidazole substituents, both pyridine substituents can be replaced by a benzimidazole substituent (i.e., n=2), or any one pyridine substituent can be replaced by a benzimidazole substituent and then R... 11 ~R 18The other pyridine substituent (i.e., n=1) can be replaced. Furthermore, for example, R in formula (ETM-2-1) can be replaced by a benzimidazole substituent. 11 ~R 18 At least one of and by R 11 ~R 18 Replace "pyridine substituents".

[0990] Specific examples of the benzimidazole derivatives include: 1-phenyl-2-(4-(10-phenylanthracene-9-yl)phenyl)-1H-benzimidazole, 2-(4-(10-(naphthyl-2-yl)anthracene-9-yl)phenyl)-1-phenyl-1H-benzimidazole, 2-(3-(10-(naphthyl-2-yl)anthracene-9-yl)phenyl)-1-phenyl-1H-benzimidazole, 5-(10-(naphthyl-2-yl)anthracene-9-yl)-1,2-diphenyl-1H-benzimidazole Imidazole, 1-(4-(10-(naphth-2-yl)anthracene-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazol, 2-(4-(9,10-bis(naphth-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazol, 1-(4-(9,10-bis(naphth-2-yl)anthracene-2-yl)phenyl)-2-phenyl-1H-benzo[d]imidazol, 5-(9,10-bis(naphth-2-yl)anthracene-2-yl)-1,2-diphenyl-1H-benzo[d]imidazol, etc.

[0991] [Chemistry 219]

[0992]

[0993] The benzimidazole derivative can be manufactured using existing raw materials and existing synthetic methods.

[0994] <Phenanthroline derivatives>

[0995] Phenanthroline derivatives are, for example, compounds represented by the following formula (ETM-12) or formula (ETM-12-1). Details are described in International Publication No. 2006 / 021982.

[0996] [Chem.220]

[0997]

[0998] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzo[a]fluorene ring, finadene ring, phenanthrene ring, or triphenylene ring), and n is an integer from 1 to 4.

[0999] Various R 11 ~R 18Each of these components is independently hydrogen, alkyl (preferably an alkyl group having 1 to 24 carbon atoms), cycloalkyl (preferably a cycloalkyl group having 3 to 12 carbon atoms), or aryl (preferably an aryl group having 6 to 30 carbon atoms). Furthermore, in formula (ETM-12-1), R... 11 ~R 18 Either of them becomes a bond with φ, which is an aryl ring.

[1000] At least one hydrogen atom in each phenanthrene derivative may be substituted with deuterium.

[1001] As R 11 ~R 18 The alkyl, cycloalkyl, and aryl groups in the formula (ETM-2) can be referenced from R. 11 ~R 18 The explanation is as follows. In addition to the examples described above, other structural formulas for φ may also be listed below. Furthermore, in the following structural formulas, R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenyl, or terphenyl, and * indicates the bond position.

[1002] [Chemistry 221]

[1003]

[1004] Specific examples of the phenanthroline derivatives include: 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-bis(1,10-phenanthroline-2-yl)anthracene, 2,6-bis(1,10-phenanthroline-5-yl)pyridine, 1,3,5-tris(1,10-phenanthroline-5-yl)benzene, 9,9'-difluoro-bis(1,10-phenanthroline-5-yl), 2,9-dimethyl-4,7-biphenyl-1,10-phenanthroline (bathocuproine), 1,3-bis(2-phenyl-1,10-phenanthroline-9-yl)benzene, or compounds represented by the following structural formulas.

[1005] [Chemistry 222]

[1006]

[1007] The phenanthroline derivatives can be manufactured using existing raw materials and existing synthetic methods.

[1008] <Hydroxyquinoline metal complexes>

[1009] Hydroxyquinoline metal complexes are, for example, compounds represented by the following formula (ETM-13).

[1010] [Chemistry 223]

[1011]

[1012] In the formula, R 1 ~R 6 Each of the following can be independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy, or aryl, where M is Li, Al, Ga, Be, or Zn, and n is an integer from 1 to 3.

[1013] Specific examples of hydroxyquinoline-based metal complexes include: lithium 8-hydroxyquinoline, tris(8-hydroxyquinoline)aluminum, tris(4-methyl-8-hydroxyquinoline)aluminum, tris(5-methyl-8-hydroxyquinoline)aluminum, tris(3,4-dimethyl-8-hydroxyquinoline)aluminum, tris(4,5-dimethyl-8-hydroxyquinoline)aluminum, tris(4,6-dimethyl-8-hydroxyquinoline)aluminum, bis(2-methyl-8-hydroxyquinoline)(phenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2-methylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(3-methylphenol)aluminum, bis( 2-Methyl-8-hydroxyquinoline)(4-methylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2-phenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(3-phenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,3-dimethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,6-dimethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(3,4-dimethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(3,5-dimethylphenol)aluminum Aluminum, bis(2-methyl-8-hydroxyquinoline)(3,5-di-tert-butylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,6-diphenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,4,6-triphenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,4,6-trimethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,4,5,6-tetramethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(1-naphthol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2-naphthol)aluminum, bis(2,4-dimethyl... bis(2,4-dimethyl-8-hydroxyquinoline)(2-phenylphenol)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)(3-phenylphenol)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)(4-phenylphenol)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)(3,5-dimethylphenol)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)(3,5-ditert-butylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)aluminum-μ-oxo-bis(2-methyl-8-hydroxyquinoline)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)aluminum-μ-oxo- ...4-Dimethyl-8-hydroxyquinoline)aluminum, bis(2-methyl-4-ethyl-8-hydroxyquinoline)aluminum-μ-oxo-bis(2-methyl-4-ethyl-8-hydroxyquinoline)aluminum, bis(2-methyl-4-methoxy-8-hydroxyquinoline)aluminum-μ-oxo-bis(2-methyl-4-methoxy-8-hydroxyquinoline)aluminum, bis(2-methyl-5-cyano-8-hydroxyquinoline)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-hydroxyquinoline)aluminum, bis(2-methyl-5-trifluoromethyl-8-hydroxyquinoline)aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl-8-hydroxyquinoline)aluminum, bis(10-hydroxybenzo[h]quinoline)beryllium, etc.

[1014] The hydroxyquinoline-based metal complexes can be manufactured using existing raw materials and existing synthetic methods.

[1015] <Thiazole derivatives and benzothiazole derivatives>

[1016] Thiazole derivatives are, for example, compounds represented by the following formula (ETM-14-1).

[1017] [Chemistry 224]

[1018] φ-(thiazole substituent)n (ETM-14-1)

[1019] Benzothiazole derivatives are, for example, compounds represented by the following formula (ETM-14-2).

[1020] [Chemistry 225]

[1021] φ-(benzothiazole substituent)n (ETM-14-2)

[1022] In each formula, φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthyl ring, anthracene ring, fluorene ring, benzo[a]fluorene ring, finadene ring, phenanthrene ring, or triphenylene ring), where n is an integer from 1 to 4. The "thiazolium substituent" or "benzo[a]thiazolium substituent" is a substituent in the "pyridine substituent" of formula (ETM-2), formula (ETM-2-1), and formula (ETM-2-2) that replaces the pyridinium group with the following thiazolium or benzo[a]thiazolium substituent. At least one hydrogen in the thiazolium derivative and the benzo[a]thiazolium derivative may be substituted with deuterium.

[1023] [Chemistry 226]

[1024] * indicates the location of the bond.

[1025] φ is preferably an anthracene ring or a fluorene ring, the structure of which can be described by referring to the description in formula (ETM-2-1) or formula (ETM-2-2), where R in each formula 11 ~R 18The description in formula (ETM-2-1) or formula (ETM-2-2) can be referenced. Furthermore, formula (ETM-2-1) or formula (ETM-2-2) is described in the form of two pyridine substituents, but when they are replaced with thiazole substituents (or benzothiazole substituents), both pyridine substituents (i.e., n=2) can be replaced by a thiazole substituent (or a benzothiazole substituent), or any one pyridine substituent can be replaced by a thiazole substituent (or a benzothiazole substituent) and R... 11 ~R 18 The other pyridine substituent can be replaced (i.e., n = 1). Furthermore, for example, R in formula (ETM-2-1) can be replaced by a thiazole substituent (or a benzothiazole substituent). 11 ~R 18 At least one of and by R 11 ~R 18 Replace "pyridine substituents".

[1026] These thiazole derivatives or benzothiazole derivatives can be manufactured using existing raw materials and existing synthetic methods.

[1027] <Thiophene derivatives>

[1028] Thiol derivatives are, for example, compounds represented by the following formula (ETM-15). Details are described in Japanese Patent Application Publication No. 9-194487.

[1029] [Chemistry 227]

[1030]

[1031] X and Y are independently alkyl, cycloalkyl, alkenyl, alkoxy, alkenyloxy, alkynyl, aryl, and heteroaryl groups, which may be substituted. For details regarding these groups, please refer to the descriptions in formulas (1) and (2) and formula (ETM-7-2). Furthermore, alkenyloxy and alkynyloxy groups are formed by substituting the alkyl portion of the alkoxy group with an alkenyl or alkynyl group, respectively. For details regarding these alkenyl and alkynyl groups, please refer to the descriptions in formula (ETM-7-2).

[1032] In addition, X and Y can bond together to form a cycloalkyl ring (and a portion of which becomes unsaturated), and details of the cycloalkyl ring can be found in the description of the cycloalkyl in formulas (1) and (2).

[1033] R 1 ~R 4They are, independently, hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkyl carbonyl, aryl carbonyl, alkoxy carbonyl, aryloxy carbonyl, azo, alkyl carbonyloxy, aryl carbonyloxy, alkoxy carbonyloxy, aryloxy carbonyloxy, sulfinyl, sulfonyl, sulfanyl, silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate, isocyanate, thiocyanate, isothiocyanate, or cyano, and may be substituted by alkyl, cycloalkyl, aryl, or halogen, or may form a fused ring with adjacent substituents.

[1034] Regarding R 1 ~R 4 For details on the halogens, alkyl groups, cycloalkyl groups, alkoxy groups, aryloxy groups, amino groups, aryl groups, heteroaryl groups, alkenyl groups, and alkynyl groups, please refer to the descriptions in formulas (1) and (2).

[1035] Regarding R 1 ~R 4 For details on the alkyl, aryl, and alkoxy groups in alkyl carbonyl, aryl carbonyl, alkoxy carbonyl, aryl carbonyl, alkoxy carbonyl, and aryl carbonyl, please refer to the descriptions in formulas (1) and (2).

[1036] Examples of silyl groups include unsubstituted silyl groups and groups in which at least one of the three hydrogens of a silyl group is independently substituted by an aryl, alkyl, or cycloalkyl group, preferably ternarily substituted silyl groups, such as triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, and alkyldicycloalkylsilyl. For details regarding the aryl, alkyl, and cycloalkyl groups among them, please refer to the descriptions in formulas (1) and (2).

[1037] The so-called fused ring formed between the adjacent substituent, for example, in R 1 With R 2 R 2 With R 3 R 3 With R 4 Fused rings, whether conjugated or non-conjugated, can be formed between rings. These fused rings may contain nitrogen, oxygen, and sulfur atoms within their internal structure, and may further condense with other rings.

[1038] Among them, the preferred one is in R 1 and R 4 In the case of phenyl, X and Y are not alkyl or phenyl. Furthermore, it is preferable that they do not simultaneously satisfy the condition when R... 1 and R 4 When X is thiophene, X and Y are alkyl groups and R is... 2and R 3 It is alkyl, aryl, alkenyl or R 2 With R 3 A cycloalkyl structure formed by bonding. Additionally, it is preferable when R... 1 and R 4 When it is silane, R 2 R 3 X and Y are each independently not hydrogen or an alkyl group having 1 to 6 carbon atoms. Furthermore, it is preferable that when R is... 1 and R 2 When the structure contains a benzene ring, X and Y are not alkyl and phenyl groups, respectively.

[1039] These thiophene derivatives can be manufactured using existing raw materials and existing synthetic methods.

[1040] <Azoline derivatives>

[1041] Azoline derivatives are, for example, compounds represented by the following formula (ETM-16). Details are described in International Publication No. 2017 / 014226.

[1042] [Chemistry 228]

[1043]

[1044] In formula (ETM-16),

[1045] φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms. At least one hydrogen atom of φ may be substituted by an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 18 carbon atoms.

[1046] Y is independently -O-, -S-, or >N-Ar, where Ar is an aryl group with 6 to 12 carbon atoms or a heteroaryl group with 2 to 12 carbon atoms, and at least one hydrogen atom of Ar can be substituted by an alkyl group with 1 to 4 carbon atoms, a cycloalkyl group with 5 to 10 carbon atoms, an aryl group with 6 to 12 carbon atoms, or a heteroaryl group with 2 to 12 carbon atoms. R 1 ~R 5 Each is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, wherein the Ar in the >N-Ar and the R are... 1 ~R 5 Any one of them is a site that forms an L-bond.

[1047] L is independently selected from the groups consisting of the divalent bases represented by equation (L-1) and the divalent bases represented by equation (L-2), respectively.

[1048] [Chemistry 229]

[1049]

[1050] In equation (L-1), X 1 ~X 6 Each independently = CR 6 -or = N-, X 1 ~X 6 At least two of them are =CR 6 -, X 1 ~X 6 The two in =CR 6 -in R 6 For sites that are bonded to φ or the zoline ring, the remainder is equal to CR. 6 -in R 6 It is hydrogen.

[1051] In equation (L-2), X 7 ~X 14 Each independently = CR 6 -or = N-, X 7 ~X 14 At least two of them are =CR 6 -, X 7 ~X 14 The two in =CR 6 -in R 6 For sites that are bonded to φ or the zoline ring, the remainder is equal to CR. 6 -in R 6 It is hydrogen.

[1052] At least one hydrogen atom of L may be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 2 to 10 carbon atoms.

[1053] m is an integer from 1 to 4. When m is 2 to 4, the groups formed by the zoline ring and L can be the same or different, and...

[1054] At least one hydrogen atom in the compound represented by formula (ETM-16) may be substituted with deuterium.

[1055] The specific azoline derivatives are compounds represented by the following formula (ETM-16-1) or formula (ETM-16-2).

[1056] [Chemistry 230]

[1057]

[1058] In equations (ETM-16-1) and (ETM-16-2),

[1059] φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms. At least one hydrogen atom of φ may be substituted by an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 18 carbon atoms.

[1060] In formula (ETM-16-1), Y is independently -O-, -S-, or >N-Ar, Ar is an aryl group with 6 to 12 carbon atoms or a heteroaryl group with 2 to 12 carbon atoms, and at least one hydrogen atom of Ar can be substituted by an alkyl group with 1 to 4 carbon atoms, a cycloalkyl group with 5 to 10 carbon atoms, an aryl group with 6 to 12 carbon atoms, or a heteroaryl group with 2 to 12 carbon atoms.

[1061] In formula (ETM-16-1), R 1 ~R 4 Each is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, wherein R 1 With R 2 Same, and R 3 With R 4 same,

[1062] In formula (ETM-16-2), R 1 ~R 5 Each is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, wherein R 1 With R 2 Same, and R 3 With R 4 same,

[1063] In equations (ETM-16-1) and (ETM-16-2),

[1064] L is independently selected from the groups consisting of the divalent bases represented by equation (L-1) and the divalent bases represented by equation (L-2), respectively.

[1065] [Chemistry 231]

[1066]

[1067] In equation (L-1), X 1 ~X 6 Each independently = CR 6 -or = N-, X 1 ~X 6 At least two of them are =CR 6 -, X 1 ~X 6 The two in =CR 6 -in R 6 For sites that are bonded to φ or the zoline ring, the remainder is equal to CR. 6 -in R6 It is hydrogen.

[1068] In equation (L-2), X 7 ~X 14 Each independently = CR 6 -or = N-, X 7 ~X 14 At least two of them are =CR 6 -, X 7 ~X 14 The two in =CR 6 -in R 6 For sites that are bonded to φ or the zoline ring, the remainder is equal to CR. 6 -in R 6 It is hydrogen.

[1069] At least one hydrogen atom of L may be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 2 to 10 carbon atoms.

[1070] m is an integer from 1 to 4. When m is 2 to 4, the groups formed by the zoline ring and L can be the same or different, and...

[1071] At least one hydrogen atom in the compound represented by formula (ETM-16-1) or formula (ETM-16-2) may be substituted with deuterium.

[1072] Preferably, φ is selected from the group consisting of a monovalent group represented by formula (φ1-1) to (φ1-18), a divalent group represented by formula (φ2-1) to (φ2-34), a trivalent group represented by formula (φ3-1) to (φ3-3) and a tetravalent group represented by formula (φ4-1) to (φ4-2), wherein at least one hydrogen of φ may be substituted by an alkyl group having 1 to 6 carbons, a cycloalkyl group having 3 to 14 carbons, an aryl group having 6 to 18 carbons, or a heteroaryl group having 2 to 18 carbons.

[1073] [Chemistry 232]

[1074]

[1075] [Chemistry 233]

[1076]

[1077] [Chemistry 234]

[1078]

[1079] In the formula, Z is greater than CR. 2 >N-Ar, >NL, -O- or -S-, >CR 2In the formulas, R is independently an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 2 to 12 carbon atoms. R can bond with each other to form a ring. In the formula >N-Ar, Ar is an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 2 to 12 carbon atoms. In the formula >NL, L is L in formula (ETM-16), formula (ETM-16-1), or formula (ETM-16-2). * indicates the bonding position.

[1080] Preferably, L is a divalent group of a ring selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthidine, phthalazine, quinoxaline, quinazoline, cycloazolinine, cycloalmine, and pteridine, and at least one hydrogen of L may be substituted by an alkyl group having 1 to 4 carbons, a cycloalkyl group having 5 to 10 carbons, an aryl group having 6 to 10 carbons, or a heteroaryl group having 2 to 10 carbons.

[1081] Preferably, the Ar in the >N-Ar of Y or Z is selected from the group consisting of phenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, naphthidyl, phthalazinyl, quinoxolinyl, quinazolinyl, cycloazolinyl, terpineyl, and pteridinyl, and at least one hydrogen atom in the >N-Ar of Y may be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms.

[1082] Preferred option: R 1 ~R 4 Each is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, wherein R 1 With R 2 Same, R 3 With R 4 Same, and R 1 ~R 4 Not all of them will become hydrogen at the same time, and m is 1 or 2. When m is 2, the group formed by the azoline ring and L is the same.

[1083] Specific examples of azoline derivatives include the following compounds. Furthermore, "Me" in the structural formula represents a methyl group.

[1084] [Chemistry 235]

[1085]

[1086] [Chemistry 236]

[1087]

[1088] More preferably, φ is selected from the group consisting of divalent groups represented by formulas (2-1), (2-31), (2-32), (2-33), and (2-34) below, wherein at least one hydrogen atom of φ may be substituted by an aryl group having 6 to 18 carbon atoms.

[1089] [Chemistry 237]

[1090]

[1091] (* indicates the location of the bond)

[1092] L is a divalent group of a ring selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine, and triazine. At least one hydrogen atom of L may be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 2 to 14 carbon atoms.

[1093] The Ar in the >N-Ar of Y is selected from the group consisting of phenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, and at least one hydrogen atom of Ar may be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms.

[1094] R 1 ~R 4 Each is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, wherein R 1 With R 2 Same, R 3 With R 4 Same, and R does not exist. 1 ~R 4 The case where all of them simultaneously become hydrogen.

[1095] m is 2, and the group formed by the zoline ring and L is the same.

[1096] Other specific examples of azoline derivatives include the following compounds. Furthermore, "Me" in the structural formula represents a methyl group.

[1097] [Chemistry 238]

[1098]

[1099] For details regarding the alkyl, cycloalkyl, aryl, or heteroaryl groups in the various formulas specifying the zoline derivatives, please refer to the descriptions in formulas (1) and (2).

[1100] The azoline derivative can be manufactured using existing raw materials and existing synthetic methods.

[1101] <Reducing substances>

[1102] The electron transport layer or electron injection layer may further include a substance that can reduce the material forming the electron transport layer or electron injection layer. The reducing substance can be any substance possessing a certain reducing property, and for example, preferably at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals.

[1103] Preferred reducing agents include Na (work function 2.36 eV), K (work function 2.28 eV), and R. b Alkali metals such as Cs (work function 2.16 eV) or Cs (work function 1.95 eV), or alkaline earth metals such as Ca (work function 2.9 eV), Sr (work function 2.0 eV–2.5 eV), or Ba (work function 2.52 eV), are preferred, especially substances with a work function of 2.9 eV or less. Among these, K and R are more preferred reducing agents. b Or alkali metals of Cs, and more preferably R b Or Cs, with Cs being the most preferred. These alkali metals have particularly high reducing power. By adding relatively small amounts of these alkali metals to the materials forming the electron transport layer or electron injection layer, the luminous brightness or lifetime of organic EL devices can be improved. In addition, combinations of two or more of these alkali metals, which have a work function of 2.9 eV or less, are also preferred as reducing agents, and combinations containing Cs are particularly preferred, such as Cs with Na, Cs with K, and Cs with R. b Alternatively, Cs can be combined with Na and K. By including Cs, reduction capabilities can be effectively utilized, and by adding it to materials that form electron transport layers or electron injection layers, the luminous brightness or lifetime of organic EL devices can be improved.

[1104] 3. Substrate for organic electroluminescent devices

[1105] The substrate 101 serves as the support for the organic EL element 100 and is typically made of quartz, glass, metal, or plastic. Depending on the purpose, the substrate 101 can be formed in the form of a plate, film, or sheet; for example, glass plates, metal plates, metal foils, plastic films, or plastic sheets can be used. Preferably, it is made of glass or transparent synthetic resins such as polyester, polymethyl methacrylate, polycarbonate, or polysulfone. If a glass substrate is used, soda-lime glass or alkali-free glass can be used. The thickness is only required to maintain sufficient mechanical strength; for example, 0.2 mm or more is sufficient. The upper limit for thickness is, for example, 2 mm or less, preferably 1 mm or less. Regarding the glass material, since the amount of dissolved ions from the glass should be minimal, alkali-free glass is preferred. Since soda-lime glass with an insulating coating such as SiO2 is commercially available, it can also be used. In addition, to improve gas barrier properties, a fine gas barrier film such as a silicon oxide film may be provided on at least one side of the substrate 101. In particular, when a plate, film or sheet made of synthetic resin with low gas barrier properties is used as the substrate 101, it is preferable to provide a gas barrier film.

[1106] 4. Anode of organic electroluminescent devices

[1107] The anode 102 functions to inject holes into the light-emitting layer 105. Furthermore, when a hole injection layer 103 and / or a hole transport layer 104 are provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 via these layers.

[1108] Materials forming the anode 102 can include both inorganic and organic compounds. Examples of inorganic compounds include: metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (oxides of indium, oxides of tin, indium tin oxide (ITO), indium zinc oxide (IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, or Nesa glass, etc. Examples of organic compounds include: conductive polymers such as poly(3-methylthiophene), polypyrrole, and polyaniline, etc. Furthermore, suitable materials that can be used as the anode of organic EL elements can be selected for use.

[1109] The resistance of the transparent electrode is not limited as long as it can supply sufficient current for the light-emitting element to emit light. However, from the viewpoint of power consumption of the light-emitting element, low resistance is ideal. For example, an ITO substrate with a resistance of 300 Ω / □ or less can function as an electrode for the element. However, since substrates with a resistance of around 10 Ω / □ are currently available, it is particularly ideal to use a low-resistance material, such as 100 Ω / □ to 5 Ω / □, preferably 50 Ω / □ to 5 Ω / □. The thickness of the ITO can be arbitrarily selected according to the resistance value, but it is usually used in the range of 50 nm to 300 nm.

[1110] 5. Hole injection layer and hole transport layer of organic electroluminescent devices

[1111] Hole injection layer 103 efficiently injects holes migrating from anode 102 into light-emitting layer 105 or hole transport layer 104. Hole transport layer 104 efficiently transports holes injected from anode 102, or holes injected from anode 102 via hole injection layer 103, to light-emitting layer 105. Hole injection layer 103 and hole transport layer 104 are formed by layering or mixing one or more hole injection / transport materials, or by a mixture of hole injection / transport materials and polymer binders. Alternatively, inorganic salts such as ferric chloride (III) can be added to the hole injection / transport materials to form the layers.

[1112] As a hole injection / transport material, it is necessary to efficiently inject / transport holes from the positive electrode between electrodes to which an electric field is applied. Ideally, it should have high hole injection efficiency and efficient transport of the injected holes. Therefore, a material with a low ionization potential, high hole mobility, and thus excellent stability, and which is less likely to generate impurities that could become traps during manufacturing and use, is preferred.

[1113] As the material for forming the hole injection layer 103 and the hole transport layer 104, any material may be selected from compounds commonly used as hole charge transport materials in photoconductive materials, existing materials used in hole injection layers and hole transport layers of p-type semiconductors and organic EL devices. Specific examples of these materials include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), bis(N-arylcarbazole) or bis(N-alkylcarbazole) and other biscarbazole derivatives, triarylamine derivatives (polymers with aromatic tertiary amino groups in the main chain or side chain), 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N 4 N 4 '-Diphenyl-N 4 N 4 '-Bis(9-phenyl-9H-carbazole-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N 4 N 4 N 4 ',N 4 '-Tetra[1,1'-biphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine, 4,4',4”-tris(3-methylphenyl(phenyl)amino)triphenylamine, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1': The following compounds are preferred: triphenylamine derivatives such as [4',1”-terphenyl]-4-amine and starburst amine derivatives; stilbene derivatives; phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.); pyrazoline derivatives; hydrazone compounds; benzofuran derivatives or thiophene derivatives; oxadiazole derivatives; quinoxaline derivatives (e.g., 1,4,5,8,9,12-hexaazatriphenyl-2,3,6,7,10,11-hexacarbononitriles, etc.); heterocyclic compounds such as porphyrin derivatives; and polysilanes. Among polymer systems, polycarbonate or styrene derivatives, polyvinylcarbazole, and polysilanes having the monomers described above in their side chains are preferred. However, there are no particular limitations as long as the compound forms a thin film required for manufacturing a light-emitting element and can inject holes from the anode and transport holes.

[1114] Furthermore, it is known that the conductivity of organic semiconductors is strongly affected by their doping. Such organic semiconductor matrix materials contain compounds with good electron-donating or electron-accepting properties. For doping with electron-donating materials, strong electron acceptors are known, such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluorotetetracyano-1,4-benzoquinodimethane (F4TCNQ) (see, for example, the literature "M. Pfeiffer, A. Bayer, T. Fritz, K. Leo"). Beyer, T. Fritz, K. Leo, Appl. Phys. Letters, 73(22), 3202-3204 (1998) and the literature J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Letters, 73(6), 729-731 (1998)). They generate so-called holes through electron migration processes in electron-donating basic matter (hole-transporting matter). The conductivity of the basic matter varies considerably depending on the number and mobility of holes. As matrix materials with hole transport properties, such as benzidine derivatives (N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)benzidine (TPD), etc.) or starburst amine derivatives (4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA), etc.), or specific metal phthalocyanines (especially zinc phthalocyanine (ZnPc), etc.) (Japanese Patent Application Publication No. 2005-167175).

[1115] 6. Cathode of organic electroluminescent devices

[1116] The cathode 108 functions to inject electrons into the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106.

[1117] The material forming the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, and the same material as the material forming the anode 102 can be used. Preferred materials include metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or alloys thereof (magnesium-silver alloys, magnesium-indium alloys, lithium fluoride / aluminum and other aluminum-lithium alloys, etc.). To improve electron injection efficiency and thus enhance device characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective. However, these low work function metals are generally unstable in the atmosphere. To improve this aspect, methods for using highly stable electrodes by doping trace amounts of lithium, cesium, or magnesium into the organic layer are known, for example. Other dopants include inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. However, these are not the only options.

[1118] Furthermore, the following are preferred examples: metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys of these metals, are layered to protect the electrodes; inorganic materials such as silicon dioxide, titanium dioxide, and silicon nitride are also used; as well as polyvinyl alcohol, vinyl chloride, and hydrocarbon polymers are layered. There are no particular restrictions on the methods used to fabricate these electrodes, as long as they are methods that achieve conductivity, such as resistance heating, electron beam evaporation, sputtering, ion plating, and coating.

[1119] 7. Adhesives that can be used in the layers of an organic electroluminescent element.

[1120] The materials used in the hole injection layer, hole transport layer, light emission layer, electron transport layer, and electron injection layer can be formed individually or dispersed in solvent-soluble resins such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resins, ketone resins, phenoxy resins, polyamides, ethyl cellulose, vinyl acetate resins, acrylonitrile butadiene styrene (ABS) resins, and polyurethane resins, or curable resins such as phenolic resins, xylene resins, petroleum resins, urea resins, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, and silicone resins.

[1121] <<Methods for Fabricating Organic Electroluminescent Element>>

[1122] The layers constituting an organic electroluminescent (EL) element can be formed by depositing thin films of the materials to be formed into each layer using methods such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination, printing, inkjet printing, spin coating, casting, and coating. The film thickness of each layer formed by these methods is not particularly limited and can be appropriately set according to the properties of the material, but is typically in the range of 2 nm to 5000 nm. The film thickness can usually be measured using a crystal oscillating film thickness measuring device. When using vapor deposition for thin film formation, the vapor deposition conditions vary depending on the type of material, the target crystalline structure of the film, and the associative structure. The preferred vapor deposition conditions are typically set within the range of: boat heating temperature +50°C to +400°C, vacuum degree 10⁻⁶ Pa to 10⁻³ Pa, vapor deposition rate 0.01 nm / s to 50 nm / s, substrate temperature -150°C to +300°C, and film thickness 2 nm to 5 μm.

[1123] Next, as an example of a method for fabricating an organic EL device, a method for fabricating an organic EL device comprising an anode, a hole injection layer, a hole transport layer, a light-emitting layer containing a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode will be described. On a suitable substrate, an anode is fabricated by forming a thin film of an anode material using a vapor deposition method or the like. Then, thin films of a hole injection layer and a hole transport layer are formed on the anode. A thin film containing a host material and a dopant material is co-deposited on the thin film to form a light-emitting layer. An electron transport layer and an electron injection layer are formed on the light-emitting layer. Finally, a thin film containing a cathode material is formed using a vapor deposition method or the like to form a cathode, thereby obtaining the target organic EL device. Alternatively, in the fabrication of the organic EL device, the fabrication order can be reversed, fabricating the cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode in that order.

[1124] When a DC voltage is applied to the organic EL element obtained in the manner described above, it is sufficient to apply the voltage with the anode as the positive polarity and the cathode as the negative polarity. If a voltage of approximately 2V to 40V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, or both). Furthermore, the organic EL element also emits light when a pulsed current or alternating current is applied. Moreover, the waveform of the applied alternating current can be arbitrary.

[1125] <<Examples of Applications of Organic Electroluminescent Elements>>

[1126] In addition, the present invention can also be applied to display devices including organic EL elements or lighting devices including organic EL elements.

[1127] Display devices or lighting devices including organic EL elements can be manufactured by existing methods such as connecting the organic EL element of this embodiment with an existing driving device, and can be driven by existing driving methods such as DC driving, pulse driving, and AC driving.

[1128] Examples of display devices include: panel displays such as color flat panel displays, flexible displays such as flexible color organic electroluminescent (EL) displays, etc. (see, for example, Japanese Patent Application Publication No. 10-335066, Japanese Patent Application Publication No. 2003-321546, Japanese Patent Application Publication No. 2004-281086, etc.). Furthermore, examples of display methods include matrix and / or segment display methods. Moreover, matrix display and segment display can coexist on the same panel.

[1129] A matrix refers to a two-dimensional arrangement of pixels for display, such as a grid or mosaic pattern, to display text or images. The shape or size of the pixels is determined by the application. For example, in the image and text display of personal computers, monitors, and televisions, quadrilateral pixels with one side less than 300μm are typically used. In contrast, in large displays such as display panels, pixels with one side in the millimeter range are used. In monochrome displays, pixels of the same color are simply arranged; in color displays, red, green, and blue pixels are displayed side-by-side. Typical matrix types include triangular and striped patterns. Furthermore, the driving method for this matrix can be either a line-sequential driving method or an active matrix. Line-sequential driving has the advantage of structural simplicity, but when considering operational characteristics, active matrices are sometimes superior; therefore, the driving method should be chosen based on the application.

[1130] In the segmented method (type), a pattern is formed to display pre-determined information, causing the designated area to illuminate. Examples include: time or temperature displays on digital clocks or thermometers, operating status displays on audio equipment or induction cookers, and dashboard displays in automobiles.

[1131] Examples of lighting devices include indoor lighting and backlights for liquid crystal displays (e.g., see Japanese Patent Application Publication Nos. 2003-257621, 2003-277741, and 2004-119211). Backlights are primarily used to improve the visibility of non-self-emissive display devices, such as liquid crystal displays, watches, audio devices, automotive panels, display boards, and signs. In particular, for backlights used in personal computers where thinness is a problem in liquid crystal displays, considering the difficulty in achieving thinness with existing methods due to the inclusion of fluorescent lamps or light guide plates, the backlight using the light-emitting element of this embodiment is characterized by its thinness and light weight.

[1132] [Example]

[1133] The present invention will be described in more detail below through examples, but the present invention is not limited to these examples. First, the synthesis examples of the compounds used in the examples will be described below.

[1134] Synthesis Example (1-1): Synthesis of Compound (1-1)

[1135] [Chemistry 239]

[1136]

[1137] Compound (1-1) was synthesized according to the method described in International Publication No. 2006 / 003842.

[1138] Synthetic Examples (1-2): Synthesis of Compound (1-12)

[1139] [Chemistry 240]

[1140]

[1141] Compounds (1-12) were synthesized according to the method described in International Publication No. 2006 / 003842.

[1142] Synthetic Examples (1-3): Synthesis of Compounds (1-16)

[1143] [Chemistry 241]

[1144]

[1145] Compounds (1-16) were synthesized according to the method described in International Publication No. 2006 / 003842.

[1146] Synthetic Examples (1-4): Synthesis of Compound (1-47)

[1147] [Chemistry 242]

[1148]

[1149] Compounds (1-47) were synthesized according to the method described in International Publication No. 2006 / 003842.

[1150] Synthetic Examples (1-5): Synthesis of Compound (1-153)

[1151] [Chemistry 243]

[1152]

[1153] Compound (1-153) was synthesized according to the method described in International Publication No. 2006 / 003842.

[1154] Synthetic Examples (1-6): Synthesis of Compound (1-255)

[1155] [Chemistry 244]

[1156]

[1157] Compound (1-255) was synthesized according to the method described in International Publication No. 2006 / 003842.

[1158] Synthetic Examples (1-7): Synthesis of Compound (1-263)

[1159] [Chemistry 245]

[1160]

[1161] Compound (1-263) was synthesized according to the method described in International Publication No. 2006 / 003842.

[1162] Synthetic Examples (1-8): Synthesis of Compound (1-319)

[1163] [Chemistry 246]

[1164]

[1165] Compound (1-319) was synthesized according to the method described in International Publication No. 2006 / 003842.

[1166] Synthetic Examples (1-9): Synthesis of Compound (1-454)

[1167] [Chemistry 247]

[1168]

[1169] Compound (1-454) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 496.

[1170] [Chemistry 248]

[1171]

[1172] Synthetic Examples (1-10): Synthesis of Compound (1-457)

[1173] [Chemistry 249]

[1174]

[1175] Compound (1-457) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 596.

[1176] [Chemistry 250]

[1177]

[1178] Synthetic Examples (1-11): Synthesis of Compound (1-456)

[1179] [Chemistry 251]

[1180]

[1181] Compound (1-456) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 596.

[1182] [Chemistry 252]

[1183]

[1184] Synthetic Examples (1-12): Synthesis of Compound (1-490)

[1185] [Chemistry 253]

[1186]

[1187] Compound (1-490) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 546.

[1188] [Chemistry 254]

[1189]

[1190] Synthetic Examples (1-13): Synthesis of Compound (1-493)

[1191] [Chemistry 255]

[1192]

[1193] Compound (1-493) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 646.

[1194] [Chemistry 256]

[1195]

[1196] Synthetic Examples (1-14): Synthesis of Compound (1-492)

[1197] [Chemistry 257]

[1198]

[1199] Compound (1-492) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 646.

[1200] [Chemistry 258]

[1201]

[1202] Synthetic Examples (1-15): Synthesis of Compound (1-641)

[1203] [Chemistry 259]

[1204]

[1205] Compound (1-641) was synthesized according to the method described in International Publication No. 2009 / 142230.

[1206] Synthetic Examples (1-16): Synthesis of Compound (1-646)

[1207] [Chemistry 260]

[1208]

[1209] Compound (1-646) was synthesized according to the method described in International Publication No. 2009 / 142230.

[1210] Synthetic Example (1-17): Synthesis of Compound (1-649)

[1211] [Chemistry 261]

[1212]

[1213] Compound (1-649) was synthesized according to the method described in International Publication No. 2009 / 142230.

[1214] Synthetic Examples (1-18): Synthesis of Compound (1-640)

[1215] [Chemistry 262]

[1216]

[1217] Compound (1-640) was synthesized according to the method described in International Publication No. 2009 / 142230.

[1218] Synthetic Example (1-19): Synthesis of Compound (1-535)

[1219] [Chemistry 263]

[1220]

[1221] Compound (1-535) was synthesized according to the method described in International Publication No. 2009 / 142230.

[1222] Synthetic Examples (1-20): Synthesis of Compound (1-534)

[1223] [Chemistry 264]

[1224]

[1225] Compound (1-534) was synthesized according to the method described in International Publication No. 2009 / 142230.

[1226] Synthetic Examples (1-21): Synthesis of Compound (1-677)

[1227] [Chemistry 265]

[1228]

[1229] Compound (1-677) was synthesized by means of a starting material compound with appropriate modifications to the method described in International Publication No. 2009 / 142230. EI-MS: m / z = 708.

[1230] Synthetic Example (1-22): Synthesis of Compound (1-682)

[1231] [Chemistry 266]

[1232]

[1233] Compound (1-682) was synthesized by means of a starting material compound with appropriate modifications to the method described in International Publication No. 2009 / 142230. EI-MS: m / z = 784.

[1234] Synthetic Example (1-23): Synthesis of Compound (1-1334)

[1235] [Chemistry 267]

[1236]

[1237] Compound (1-1334) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 587.

[1238] [Chemistry 268]

[1239]

[1240] Synthetic Examples (1-24): Synthesis of Compound (1-1336)

[1241] [Chemistry 269]

[1242]

[1243] Compound (1-1336) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 637.

[1244] [Chemistry 270]

[1245]

[1246] Synthetic Examples (1-25): Synthesis of Compound (1-279)

[1247] [Chemistry 271]

[1248]

[1249] Compound (1-279) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 737.

[1250] [Chemistry 272]

[1251]

[1252] Synthetic Examples (1-26): Synthesis of Compound (1-125)

[1253] [Chemistry 273]

[1254]

[1255] Compound (1-125) was synthesized according to the method described in International Publication No. 2006 / 003842.

[1256] Synthetic Examples (1-27): Synthesis of Compound (1-155)

[1257] [Chemistry 274]

[1258]

[1259] Compound (1-155) was synthesized according to the method described in International Publication No. 2006 / 003842.

[1260] Synthetic Examples (1-28): Synthesis of Compound (1-29)

[1261] [Chemistry 275]

[1262]

[1263] Compounds (1-29) were synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 587.

[1264] [Chemistry 276]

[1265]

[1266] Synthetic Examples (1-29): Synthesis of Compound (1-276)

[1267] [Chemistry 277]

[1268]

[1269] Compound (1-276) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 637.

[1270] [Chemistry 278]

[1271]

[1272] Synthetic Examples (1-30): Synthesis of Compound (1-448)

[1273] [Chemistry 279]

[1274]

[1275] Compound (1-448) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 671.

[1276] [Chemistry 280]

[1277]

[1278] Synthetic Examples (1-31): Synthesis of Compound (1-13)

[1279] [Chemistry 281]

[1280]

[1281] Compounds (1-13) were synthesized by means of reactant compounds with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 658.

[1282] [Chemistry 282]

[1283]

[1284] Synthetic Examples (1-32): Synthesis of Compound (1-287)

[1285] [Chemistry 283]

[1286]

[1287] Compound (1-287) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 532.

[1288] [Chemistry 284]

[1289]

[1290] Synthetic Examples (1-33): Synthesis of Compound (1-124)

[1291] [Chemistry 285]

[1292]

[1293] Compound (1-124) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 482.

[1294] [Chemistry 286]

[1295]

[1296] Synthetic Examples (1-34): Synthesis of Compounds (1-4)

[1297] [Chemistry 287]

[1298]

[1299] Compounds (1-4) were synthesized by means of reactant compounds with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 558.

[1300] [Chemistry 288]

[1301]

[1302] Synthetic Example (1-35): Synthesis of Compound (1-807)

[1303] [Chemistry 289]

[1304]

[1305] Compound (1-807) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 546.

[1306] [Chemistry 290]

[1307]

[1308] Synthetic Example (1-36): Synthesis of Compound (1-802)

[1309] [Chemistry 291]

[1310]

[1311] Compound (1-802) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 496.

[1312] [Chemistry 292]

[1313]

[1314] Synthetic Example (1-37): Synthesis of Compound (1-2400)

[1315] [Chemistry 293]

[1316]

[1317] Compound (1-2400) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 532.

[1318] [Chemistry 294]

[1319]

[1320] Synthetic Example (1-38): Synthesis of Compound (1-2401)

[1321] [Chemistry 295]

[1322]

[1323] Compound (1-2401) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 482.

[1324] [Chemistry 296]

[1325]

[1326] Synthetic Example (1-39): Synthesis of Compound (1-4133)

[1327] Compound (1-4133) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 609.

[1328] [Chemistry 297]

[1329]

[1330] Synthetic Examples (1-40): Synthesis of Compounds (1-148)

[1331] Compound (1-148) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 533.

[1332] [Chemistry 298]

[1333]

[1334] Synthetic Examples (1-41): Synthesis of Compounds (1-150)

[1335] Compound (1-150) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 633.

[1336] [Chemistry 299]

[1337]

[1338] Synthetic Examples (1-42): Synthesis of Compound (1-136)

[1339] Compound (1-136) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 533.

[1340] [Chemical 300]

[1341]

[1342] Synthetic Example (1-43): Synthesis of Compound (1-4155)

[1343] Compound (1-4155) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 583.

[1344] [Chemical Engineering 301]

[1345]

[1346] Synthetic Examples (1-44): Synthesis of Compound (1-3268)

[1347] Compound (1-3268) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[1348] [Chemical 302]

[1349]

[1350] Synthetic Example (1-45): Synthesis of Compound (1-4114)

[1351] Compound (1-4114) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[1352] [Chemical 303]

[1353]

[1354] Synthetic Example (1-46): Synthesis of Compound (1-4121)

[1355] Compound (1-4121) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[1356] [Chemical 304]

[1357]

[1358] Synthetic Examples (1-47): Synthesis of Compound (1-4119)

[1359] Compound (1-4119) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[1360] [Chemical 305]

[1361]

[1362] Synthetic Example (1-48): Synthesis of Compound (1-4120)

[1363] Compound (1-4120) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 663.

[1364] [Chemical 306]

[1365]

[1366] Synthetic Example (1-49): Synthesis of Compound (1-4107)

[1367] Compound (1-4107) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 663.

[1368] [Chemical 307]

[1369]

[1370] Synthetic Examples (1-50): Synthesis of Compound (1-4317)

[1371] Compound (1-4317) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 583.

[1372] [Chemical 308]

[1373]

[1374] Synthetic Examples (1-51): Synthesis of Compound (1-4327)

[1375] Compound (1-4327) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 633.

[1376] [Chemical 309]

[1377]

[1378] Synthetic Examples (1-52): Synthesis of Compound (1-3991)

[1379] Compound (1-3991) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[1380] [Chemical 310]

[1381]

[1382] Synthetic Examples (1-53): Synthesis of Compound (1-2984)

[1383] Compound (1-2984) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[1384] [Chemistry 311]

[1385]

[1386] Synthetic Examples (1-54): Synthesis of Compounds (1-3452)

[1387] Compound (1-3452) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 649.

[1388] [Chemistry 312]

[1389]

[1390] Synthetic Examples (1-55): Synthesis of Compound (1-2883)

[1391] Compound (1-2883) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 649.

[1392] [Chemistry 313]

[1393]

[1394] Synthetic Example (1-56): Synthesis of Compound (1-4205)

[1395] Under nitrogen atmosphere, intermediate (I-2) (1.0 g) was dissolved in toluene (100 ml), and intermediate (I-1) (1.0 g), potassium carbonate (1.4 g), tetrabutylammonium bromide (TBAB, 0.4 g), and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (Pd-132, 0.35 g) were added. The mixture was stirred under reflux for 5 hours. After the reaction, water was added to stop the reaction, and then toluene was added for liquid-liquid extraction. The organic layer was then concentrated to obtain the crude product. The crude product was purified using a short silica gel column (elution: chlorobenzene) to obtain compound (1-4205) (0.85 g). EI-MS: m / z = 608.

[1396] [Chemical 314]

[1397]

[1398] Synthetic Example (1-57): Synthesis of Compound (1-4232)

[1399] Compound (1-4232) was synthesized by appropriately modifying the starting material compound used in the synthetic examples (1-56). EI-MS: m / z = 658.

[1400] [Chemical 315]

[1401]

[1402] Synthetic Examples (1-58): Synthesis of Compound (1-4219)

[1403] Compound (1-4219) was synthesized by appropriately modifying the starting material compound used in the synthetic examples (1-56). EI-MS: m / z = 608.

[1404] [Chemistry 316]

[1405]

[1406] Synthetic Examples (1-59): Synthesis of Compound (1-4254)

[1407] Compound (1-4254) was synthesized by appropriately modifying the starting material compound used in the method described in synthetic examples (1-56). EI-MS: m / z = 634.

[1408] [Chemistry 317]

[1409]

[1410] Synthetic Examples (1-60): Synthesis of Compound (1-4263)

[1411] Compound (1-4263) was synthesized by appropriately modifying the starting material compound used in the method described in synthetic examples (1-56). EI-MS: m / z = 658.

[1412] [Chemistry 318]

[1413]

[1414] Synthetic Examples (1-61): Synthesis of Compound (1-4271)

[1415] Compound (1-4271) was synthesized by appropriately modifying the starting material compound used in the method described in Synthetic Examples (1-56). EI-MS: m / z = 708.

[1416] [Chemistry 319]

[1417]

[1418] Synthetic Examples (1-62): Synthesis of Compound (1-2995)

[1419] Compound (1-2995) was synthesized by appropriately modifying the starting material compound used in the method described in Synthetic Examples (1-56). EI-MS: m / z = 648.

[1420] [Chem.320]

[1421]

[1422] Synthetic Example (1-63): Synthesis of Compound (1-3005)

[1423] Compound (1-3005) was synthesized by appropriately modifying the starting material compound used in the method described in Synthetic Examples (1-56). EI-MS: m / z = 648.

[1424] [Chemistry 321]

[1425]

[1426] Synthetic Example (1-64): Synthesis of Compound (1-3020)

[1427] Compound (1-3020) was synthesized by appropriately modifying the starting material compound used in the method described in Synthetic Examples (1-56). EI-MS: m / z = 750.

[1428] [Chemistry 322]

[1429]

[1430] Synthetic Example (1-65): Synthesis of Compound (1-4204)

[1431] Compound (1-4204) was synthesized by appropriately modifying the starting material compound used in the method described in Synthetic Examples (1-56). EI-MS: m / z = 708.

[1432] [Chemistry 323]

[1433]

[1434] Synthetic Examples (1-66): Synthesis of Compound (1-4198)

[1435] Compound (1-4198) was synthesized by appropriately modifying the starting material compound used in the method described in synthetic examples (1-56). EI-MS: m / z = 788.

[1436] [Chemistry 324]

[1437]

[1438] Synthetic Examples (1-67): Synthesis of Compound (1-4280)

[1439] Compound (1-4280) was synthesized by appropriately modifying the starting material compound used in the method described in Synthetic Examples (1-56). EI-MS: m / z = 734.

[1440] [Chemistry 325]

[1441]

[1442] Synthetic Examples (1-68): Synthesis of Compound (1-3821)

[1443] Compound (1-3821) was synthesized by appropriately modifying the starting material compound used in the method described in Synthetic Examples (1-56). EI-MS: m / z = 838.

[1444] [Chemistry 326]

[1445]

[1446] Synthetic Examples (1-69): Synthesis of Compound (1-3078)

[1447] Compound (1-3078) was synthesized by appropriately modifying the starting material compound used in the method described in Synthetic Examples (1-56). EI-MS: m / z = 648.

[1448] [Chemistry 327]

[1449]

[1450] Synthetic Example (1-70): Synthesis of Compound (1-4209)

[1451] Compound (1-4209) was synthesized by appropriately modifying the starting material compound used in the method described in Synthetic Examples (1-56). EI-MS: m / z = 658.

[1452] [Chemistry 328]

[1453]

[1454] Synthetic Example (1-71): Synthesis of Compound (1-4093)

[1455] Compound (1-4093) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 609.

[1456] [Chemistry 329]

[1457]

[1458] Synthetic Example (1-72): Synthesis of Compound (1-4092)

[1459] Compound (1-4092) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 811.

[1460] [Chemistry 330]

[1461]

[1462] Synthetic Example (1-73): Synthesis of Compound (1-2977)

[1463] Compound (1-2977) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 699.

[1464] [Chemistry 331]

[1465]

[1466] Synthetic Example (1-74): Synthesis of Compound (1-4036)

[1467] Compound (1-4036) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 649.

[1468] [Chemistry 332]

[1469]

[1470] Synthetic Examples (1-75): Synthesis of Compound (1-4335)

[1471] Compound (1-4335) was synthesized by appropriately modifying the starting material compound used in the synthetic examples (1-56). EI-MS: m / z = 609.

[1472] [Chemistry 333]

[1473]

[1474] Synthetic Examples (1-76): Synthesis of Compound (1-4347)

[1475] Compound (1-4347) was synthesized by appropriately modifying the starting material compound used in the synthetic examples (1-56). EI-MS: m / z = 609.

[1476] [Chemistry 334]

[1477]

[1478] Synthetic Example (1-77): Synthesis of Compound (1-4354)

[1479] Compound (1-4354) was synthesized by appropriately modifying the starting material compound used in the synthetic examples (1-56). EI-MS: m / z = 659.

[1480] [Chemistry 335]

[1481]

[1482] Synthetic Examples (1-78): Synthesis of Compound (1-3751)

[1483] Compound (1-3751) was synthesized by appropriately modifying the starting material compound used in the method described in Synthetic Examples (1-56). EI-MS: m / z = 649.

[1484] [Chemistry 336]

[1485]

[1486] Synthetic Example (1-79): Synthesis of Compound (1-4106)

[1487] Compound (1-4106) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 609.

[1488] [Chemistry 337]

[1489]

[1490] Synthetic Examples (1-80): Synthesis of Compound (1-3830)

[1491] Compound (1-3830) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 533.

[1492] [Chemistry 338]

[1493]

[1494] Synthetic Examples (1-81): Synthesis of Compound (1-3839)

[1495] Compound (1-3839) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 533.

[1496] [Chemistry 339]

[1497]

[1498] Synthetic Examples (1-82): Synthesis of Compound (1-4381)

[1499] Compound (1-4381) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 583.

[1500] [Transformation 340]

[1501]

[1502] Synthetic Examples (1-83): Synthesis of Compound (1-4390)

[1503] Compound (1-4390) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 633.

[1504] [Chemistry 341]

[1505]

[1506] Synthetic Examples (1-84): Synthesis of Compound (1-3837)

[1507] Compound (1-3837) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 713.

[1508] [Chemistry 342]

[1509]

[1510] Synthetic Example (1-85): Synthesis of Compound (1-4091)

[1511] Compound (1-4091) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 533.

[1512] [Chemistry 343]

[1513]

[1514] Synthetic Examples (1-86): Synthesis of Compound (1-3859)

[1515] Compound (1-3859) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 583.

[1516] [Chemistry 344]

[1517]

[1518] Synthetic Examples (1-87): Synthesis of Compound (1-2416)

[1519] Compound (1-2416) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2019-056338. EI-MS: m / z = 583.

[1520] [Chemistry 345]

[1521]

[1522] Synthetic Examples (1-88): Synthesis of Compound (1-2495)

[1523] Compound (1-2495) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2019-056338. EI-MS: m / z = 749.

[1524] [Chemistry 346]

[1525]

[1526] Synthetic Example (1-89): Synthesis of Compound (1-2404)

[1527] Compound (1-2404) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2019-056338. EI-MS: m / z = 673.

[1528] [Chemistry 347]

[1529]

[1530] Synthetic Examples (1-90): Synthesis of Compound (1-2440)

[1531] Compound (1-2440) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2019-056338. EI-MS: m / z = 965.

[1532] [Chemistry 348]

[1533]

[1534] Synthetic Examples (1-91): Synthesis of Compound (1-2499)

[1535] Compound (1-2499) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2019-056338. EI-MS: m / z = 749.

[1536] [Chemistry 349]

[1537]

[1538] Synthetic Examples (1-92): Synthesis of Compound (1-2413)

[1539] Compound (1-2413) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2019-056338. EI-MS: m / z = 723.

[1540] [Chemical 350]

[1541]

[1542] Synthetic Example (1-93): Synthesis of Compound (1-2520)

[1543] Compound (1-2520) was synthesized by the method described in Korean Patent Publication No. 2010-007791. EI-MS: m / z = 659.

[1544] [Chemistry 351]

[1545]

[1546] Synthetic Examples (1-94): Synthesis of Compound (1-2516)

[1547] Compound (1-2516) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2010-007791. EI-MS: m / z = 839.

[1548] [Chemistry 352]

[1549]

[1550] Synthetic Examples (1-95): Synthesis of Compound (1-2519)

[1551] Compound (1-2519) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2010-007791. EI-MS: m / z = 749.

[1552] [Chemistry 353]

[1553]

[1554] Synthetic Examples (1-96): Synthesis of Compound (1-2525)

[1555] Compound (1-2525) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2010-007791. EI-MS: m / z = 749.

[1556] [Chemistry 354]

[1557]

[1558] Synthetic Example (1-97): Synthesis of Compound (1-2541)

[1559] Compound (1-2541) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 659.

[1560] [Chemistry 355]

[1561]

[1562] Synthetic Examples (1-98): Synthesis of Compound (1-2557)

[1563] Compound (1-2557) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 659.

[1564] [Chemistry 356]

[1565]

[1566] Synthetic Example (1-99): Synthesis of Compound (1-2573)

[1567] Compound (1-2573) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 709.

[1568] [Chemistry 357]

[1569]

[1570] Synthetic Examples (1-100): Synthesis of Compound (1-2586)

[1571] Compound (1-2586) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 709.

[1572] [Chemistry 358]

[1573]

[1574] Synthetic Example (1-101): Synthesis of Compound (1-2594)

[1575] Compound (1-2594) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 709.

[1576] [Chemistry 359]

[1577]

[1578] Synthetic Example (1-102): Synthesis of Compound (1-2599)

[1579] Compound (1-2599) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 709.

[1580] [Hua360]

[1581]

[1582] Synthetic Example (1-103): Synthesis of Compound (1-2728)

[1583] Compound (1-2728) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 749.

[1584] [Chemistry 361]

[1585]

[1586] Synthetic Examples (1-104): Synthesis of Compound (1-2579)

[1587] Compound (1-2579) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 889.

[1588] [Chemistry 362]

[1589]

[1590] Synthetic Examples (1-105): Synthesis of Compound (1-2696)

[1591] Compound (1-2696) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 889.

[1592] [Chemical formula 363]

[1593]

[1594] Synthesis Example (1-106): Synthesis of Compound (1-2738)

[1595] Compound (1-2738) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 799.

[1596] [Chemical formula 364]

[1597]

[1598] Synthesis Example (1-107): Synthesis of Compound (1-2743)

[1599] Compound (1-2743) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 799.

[1600] [Chemical formula 365]

[1601]

[1602] Synthesis Example (1-108): Synthesis of Compound (1-2699)

[1603] Compound (1-2699) was synthesized by appropriately changing the starting compounds of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 1041.

[1604] [Chemical formula 366]

[1605]

[1606] Synthesis Example (1-109): Synthesis of Compound (1-2603)

[1607] Compound (1-2603) was synthesized by the method described in Korean Patent Publication No. 2018-0131963. EI-MS: m / z = 749.

[1608] [Chemical formula 367]

[1609]

[1610] Synthetic Example (1-110): Synthesis of Compound (1-2756)

[1611] Compound (1-2756) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2018-0131963. EI-MS: m / z = 925.

[1612] [Chem.368]

[1613]

[1614] Synthetic Example (1-111): Synthesis of Compound (1-2627)

[1615] Compound (1-2627) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2018-0131963. EI-MS: m / z = 749.

[1616] [Chemistry 369]

[1617]

[1618] Synthetic Example (1-112): Synthesis of Compound (1-2757)

[1619] Compound (1-2757) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2018-0131963. EI-MS: m / z = 799.

[1620] [Transformation 370]

[1621]

[1622] Synthetic Example (1-113): Synthesis of Compound (1-2686)

[1623] Compound (1-2686) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2018-0131963. EI-MS: m / z = 749.

[1624] [Chemistry 371]

[1625]

[1626] Synthetic Examples (1-114): Synthesis of Compound (1-2615)

[1627] Compound (1-2615) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2018-0131963. EI-MS: m / z = 749.

[1628] [Chemistry 372]

[1629]

[1630] Synthetic Example (1-115): Synthesis of Compound (1-2640)

[1631] Compound (1-2640) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2018-0131963. EI-MS: m / z = 749.

[1632] [Chemistry 373]

[1633]

[1634] Synthetic Example (1-116): Synthesis of Compound (1-2747)

[1635] Compound (1-2747) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2018-0131963. EI-MS: m / z = 839.

[1636] [Chemistry 374]

[1637]

[1638] Synthetic Example (1-117): Synthesis of Compound (1-2641)

[1639] Compound (1-2641) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2018-0131963. EI-MS: m / z = 929.

[1640] [Chemistry 375]

[1641]

[1642] Synthetic Example (1-118): Synthesis of Compound (1-2775)

[1643] Compound (1-2775) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 735.

[1644] [Chemistry 376]

[1645]

[1646] Synthetic Example (1-119): Synthesis of Compound (1-2779)

[1647] Compound (1-2779) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 735.

[1648] [Chemistry 377]

[1649]

[1650] Synthetic Examples (1-120): Synthesis of Compound (1-2787)

[1651] Compound (1-2787) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 785.

[1652] [Chemistry 378]

[1653]

[1654] Synthetic Example (1-121): Synthesis of Compound (1-2776)

[1655] Compound (1-2776) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 915.

[1656] [Chemistry 379]

[1657]

[1658] Synthetic Example (1-122): Synthesis of Compound (1-2812)

[1659] Compound (1-2812) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 825.

[1660] [Chemistry 380]

[1661]

[1662] Synthetic Example (1-123): Synthesis of Compound (1-3914)

[1663] Compound (1-3914) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 659.

[1664] [Chemistry 381]

[1665]

[1666] Synthetic Examples (1-124): Synthesis of Compound (1-3951)

[1667] Compound (1-3951) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 749.

[1668] [Chemistry 382]

[1669]

[1670] Synthetic Example (1-125): Synthesis of Compound (1-3903)

[1671] Compound (1-3903) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 659.

[1672] [Chemistry 383]

[1673]

[1674] Synthetic Examples (1-126): Synthesis of Compound (1-1335)

[1675] Compound (1-1335) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 587.

[1676] [Chem. 384]

[1677]

[1678] Synthetic Examples (1-127): Synthesis of Compound (1-1337)

[1679] Compound (1-1337) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 637.

[1680] [Chem.385]

[1681]

[1682] Synthetic Examples (1-128): Synthesis of Compounds (1-28)

[1683] Compounds (1-28) were synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 587.

[1684] [Chemistry 386]

[1685]

[1686] Synthetic Examples (1-129): Synthesis of Compound (1-275)

[1687] Compound (1-275) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 637.

[1688] [Chemistry 387]

[1689]

[1690] Synthetic Examples (1-130): Synthesis of Compound (1-3445)

[1691] Compound (1-3445) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[1692] [Chem.388]

[1693]

[1694] Synthetic Example (1-131): Synthesis of Compound (1-3467)

[1695] Compound (1-3467) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[1696] [Chemistry 389]

[1697]

[1698] Synthetic Example (1-132): Synthesis of Compound (1-3434)

[1699] Compound (1-3434) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[1700] [Chemistry 390]

[1701]

[1702] Synthetic Example (1-133): Synthesis of Compound (1-3481)

[1703] Compound (1-3481) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[1704] [Chemistry 391]

[1705]

[1706] Synthetic Example (1-134): Synthesis of Compound (1-3408)

[1707] Compound (1-3408) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[1708] [Chemistry 392]

[1709]

[1710] Synthetic Example (1-135): Synthesis of Compound (1-3777)

[1711] Compound (1-3777) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 589.

[1712] [Chemistry 393]

[1713]

[1714] Synthetic Example (1-136): Synthesis of Compound (1-3594)

[1715] Compound (1-3594) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 623.

[1716] [Chemistry 394]

[1717]

[1718] Synthetic Example (1-137): Synthesis of Compound (1-3589)

[1719] Compound (1-3589) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 623.

[1720] [Chemistry 395]

[1721]

[1722] Synthetic Example (1-138): Synthesis of Compound (1-3440)

[1723] Compound (1-3440) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 673.

[1724] [Chemistry 396]

[1725]

[1726] Synthetic Example (1-139): Synthesis of Compound (1-3435)

[1727] Compound (1-3435) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 753.

[1728] [Chemistry 397]

[1729]

[1730] Synthetic Example (1-140): Synthesis of Compound (1-3572)

[1731] Compound (1-3572) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 699.

[1732] [Chem.398]

[1733]

[1734] Synthetic Example (1-141): Synthesis of Compound (1-3453)

[1735] Compound (1-3453) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 825.

[1736] [Chemistry 399]

[1737]

[1738] Synthetic Example (1-142): Synthesis of Compound (1-3562)

[1739] Compound (1-3562) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 623.

[1740] [Chemical 400]

[1741]

[1742] Synthetic Example (1-143): Synthesis of Compound (1-3559)

[1743] Compound (1-3559) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 623.

[1744] [Chemical Engineering 401]

[1745]

[1746] Synthetic Example (1-144): Synthesis of Compound (1-3522)

[1747] Compound (1-3522) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[1748] [Chemical 402]

[1749]

[1750] Synthetic Example (1-145): Synthesis of Compound (1-4014)

[1751] Compound (1-4014) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 739.

[1752] [Chemical 403]

[1753]

[1754] Synthetic Example (1-146): Synthesis of Compound (1-4018)

[1755] Compound (1-4018) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[1756] [Chemical 404]

[1757]

[1758] Synthetic Example (1-147): Synthesis of Compound (1-3762)

[1759] Compound (1-3762) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 623.

[1760] [Chemical 405]

[1761]

[1762] Synthetic Example (1-148): Synthesis of Compound (1-2912)

[1763] Compound (1-2912) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[1764] [Chemical 406]

[1765]

[1766] Synthetic Example (1-149): Synthesis of Compound (1-3284)

[1767] Compound (1-3284) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[1768] [Chemical 407]

[1769]

[1770] Synthetic Examples (1-150): Synthesis of Compound (1-3736)

[1771] Compound (1-3736) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 649.

[1772] [Chemical 408]

[1773]

[1774] Synthetic Example (1-151): Synthesis of Compound (1-3770)

[1775] Compound (1-3770) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 589.

[1776] [Chemical 409]

[1777]

[1778] Synthetic Example (1-152): Synthesis of Compound (1-2873)

[1779] Compound (1-2873) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 648.

[1780] [Chemical 410]

[1781]

[1782] Synthetic Example (1-153): Synthesis of Compound (1-3249)

[1783] Compound (1-3249) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 623.

[1784] [Chemistry 411]

[1785]

[1786] Synthetic Example (1-154): Synthesis of Compound (1-3296)

[1787] Compound (1-3296) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 623.

[1788] [Chemistry 412]

[1789]

[1790] Synthetic Example (1-155): Synthesis of Compound (1-2917)

[1791] Compound (1-2917) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 803.

[1792] [Chemistry 413]

[1793]

[1794] Synthetic Examples (1-156): Synthesis of Compound (1-3768)

[1795] Compound (1-3768) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 723.

[1796] [Chemistry 414]

[1797]

[1798] Synthetic Example (1-157): Synthesis of Compound (1-3780)

[1799] Compound (1-3780) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 789.

[1800] [Chemical 415]

[1801]

[1802] Synthetic Example (1-158): Synthesis of Compound (1-3963)

[1803] Compound (1-3963) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[1804] [Chemistry 416]

[1805]

[1806] Synthetic Example (1-159): Synthesis of Compound (1-4112)

[1807] Compound (1-4112) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 649.

[1808] [Chemistry 417]

[1809]

[1810] Synthetic Example (1-160): Synthesis of Compound (1-4052)

[1811] Compound (1-4052) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 699.

[1812] [Chemistry 418]

[1813]

[1814] Synthetic Example (1-161): Synthesis of Compound (1-4047)

[1815] Compound (1-4047) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 649.

[1816] [Chemistry 419]

[1817]

[1818] Synthetic Example (1-162): Synthesis of Compound (1-3778)

[1819] Compound (1-3778) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 748.

[1820] [Chem.420]

[1821]

[1822] Synthetic Example (1-163): Synthesis of Compound (1-4008)

[1823] Compound (1-4008) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 497.

[1824] [Chemistry 421]

[1825]

[1826] Synthetic Example (1-164): Synthesis of Compound (1-802)

[1827] Compound (1-802) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 497.

[1828] [Chemistry 422]

[1829]

[1830] Synthetic Example (1-165): Synthesis of Compound (1-804)

[1831] Compound (1-804) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 513.

[1832] [Chemistry 423]

[1833]

[1834] Synthetic Example (1-166): Synthesis of Compound (1-3784)

[1835] Compound (1-3784) was synthesized by modifying the raw material compound according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 547.

[1836] [Chemistry 424]

[1837]

[1838] Synthetic Example (1-167): Synthesis of Compound (1-808)

[1839] Compound (1-808) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 547.

[1840] [Chemical 425]

[1841]

[1842] Synthetic Example (1-168): Synthesis of Compound (1-801)

[1843] Compound (1-801) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 572.

[1844] [Chemistry 426]

[1845]

[1846] Synthetic Example (1-169): Synthesis of Compound (1-4142)

[1847] Compound (1-4142) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 713.

[1848] [Chemistry 427]

[1849]

[1850] Synthetic Example (1-170): Synthesis of Compound (1-4145)

[1851] Compound (1-4145) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 865.

[1852] [Chemistry 428]

[1853]

[1854] Synthetic Example (1-171): Synthesis of Compound (1-4138)

[1855] Compound (1-4138) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 713.

[1856] [Chemistry 429]

[1857]

[1858] Synthetic Example (1-172): Synthesis of Compound (1-4165)

[1859] Compound (1-4165) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 713.

[1860] [Chemistry 430]

[1861]

[1862] Synthetic Example (1-173): Synthesis of Compound (1-4168)

[1863] Compound (1-4168) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 713.

[1864] [Chemistry 431]

[1865]

[1866] Synthetic Example (1-174): Synthesis of Compound (1-4152)

[1867] Compound (1-4152) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 713.

[1868] [Chemistry 432]

[1869]

[1870] Synthetic Example (1-175): Synthesis of Compound (1-4143)

[1871] Compound (1-4143) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 623.

[1872] [Chemistry 433]

[1873]

[1874] Synthetic Example (1-176): Synthesis of Compound (1-3849)

[1875] Compound (1-3849) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 863.

[1876] [Chemistry 434]

[1877]

[1878] Synthetic Example (1-177): Synthesis of Compound (1-4434)

[1879] Compound (1-4434) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 601.

[1880] [Chemistry 435]

[1881]

[1882] Synthetic Examples (1-178): Synthesis of Compound (1-4429)

[1883] Compound (1-4429) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 601.

[1884] [Chemistry 436]

[1885]

[1886] Synthetic Example (1-179): Synthesis of Compound (1-4458)

[1887] Compound (1-4458) was synthesized by appropriately modifying the starting material compound used in the synthetic examples (1-56). EI-MS: m / z = 665.

[1888] [Chemistry 437]

[1889]

[1890] Synthetic Example (1-180): Synthesis of Compound (1-4409)

[1891] Compound (1-4409) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 587.

[1892] [Chemistry 438]

[1893]

[1894] Synthetic Example (1-181): Synthesis of Compound (1-4404)

[1895] Compound (1-4404) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 587.

[1896] [Chemistry 439]

[1897]

[1898] Synthetic Example (1-182): Synthesis of Compound (1-4427)

[1899] Compound (1-4427) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 615.

[1900] [Chemistry 440]

[1901]

[1902] Synthetic Example (1-183): Synthesis of Compound (1-2973)

[1903] Compound (1-2973) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 497.

[1904] [Chemistry 441]

[1905]

[1906] Synthetic Example (1-184): Synthesis of Compound (1-4747)

[1907] Compound (1-4747) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 573.

[1908] [Chemistry 442]

[1909]

[1910] Synthetic Example (1-185): Synthesis of Compound (1-3444)

[1911] Compound (1-3444) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 673.

[1912] [Chemistry 443]

[1913]

[1914] Synthetic Example (1-186): Synthesis of Compound (1-3450)

[1915] Compound (1-3450) was synthesized by means of a reactant compound with appropriate modifications to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 725.

[1916] [Chemistry 444]

[1917]

[1918] Synthetic Example (1-187): Synthesis of Compound (1-1355)

[1919] Compound (1-12) (1 g), 5% platinum-carbon (5% Pt / C, 300 mg), heavy water (40 mL), cyclohexane (cHex, 20 mL), and isopropanol (IPA, 5 mL) were placed in a flask under argon atmosphere and heated at 100 °C. After the reaction, water and chloroform were added for liquid-liquid extraction. The organic layer was dried with magnesium sulfate and filtered. The organic layer was concentrated and the crude product was recrystallized to obtain the target compound (1-1355).

[1920] EI-MS: m / z = 532.

[1921] [Chemistry 445]

[1922]

[1923] Synthetic Examples (1-188): Synthesis of Compound (1-1359)

[1924] The compound represented by formula (1-1359) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 532.

[1925] [Chemistry 446]

[1926]

[1927] Synthetic Examples (1-189): Synthesis of Compound (1-1390)

[1928] The compound represented by formula (1-1390) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 668.

[1929] [Chemistry 447]

[1930]

[1931] Synthetic Examples (1-190): Synthesis of Compound (1-1496)

[1932] The compound represented by formula (1-1496) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 749.

[1933] [Chemistry 448]

[1934]

[1935] Synthetic Examples (1-191): Synthesis of Compound (1-1598)

[1936] The compound represented by formula (1-1598) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 584.

[1937] [Chemistry 449]

[1938]

[1939] Synthetic Examples (1-192): Synthesis of Compound (1-1658)

[1940] The compound represented by formula (1-1658) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 584.

[1941] [Chemistry 450]

[1942]

[1943] Synthetic Examples (1-193): Synthesis of Compound (1-1789)

[1944] The compound represented by formula (1-1789) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 520.

[1945] [Chemistry 451]

[1946]

[1947] Synthetic Examples (1-194): Synthesis of Compound (1-1791)

[1948] The compound represented by formula (1-1791) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 624.

[1949] [Chemistry 452]

[1950]

[1951] Synthetic Examples (1-195): Synthesis of Compound (1-1825)

[1952] The compound represented by formula (1-1825) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 572.

[1953] [Chemistry 453]

[1954]

[1955] Synthetic Examples (1-196): Synthesis of Compound (1-1468)

[1956] The compound represented by formula (1-1468) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 668.

[1957] [Chemistry 454]

[1958]

[1959] Synthetic Examples (1-197): Synthesis of Compound (1-1498)

[1960] The compound represented by formula (1-1498) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 908.

[1961] [Chemistry 455]

[1962]

[1963] Synthetic Examples (1-198): Synthesis of Compound (1-2389)

[1964] The compound represented by formula (1-2389) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 664.

[1965] [Chemistry 456]

[1966]

[1967] Synthetic Examples (1-199): Synthesis of Compound (1-1618)

[1968] The compound represented by formula (1-1618) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 768.

[1969] [Chemistry 457]

[1970]

[1971] Synthetic Examples (1-200): Synthesis of Compound (1-1372)

[1972] The compound represented by formula (1-1372) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 612.

[1973] [Chemistry 458]

[1974]

[1975] Synthetic Example (1-201): Synthesis of Compound (1-1615)

[1976] The compound represented by formula (1-1615) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 664.

[1977] [Chemistry 459]

[1978]

[1979] Synthetic Example (1-202): Synthesis of Compound (1-1783)

[1980] The compound represented by formula (1-1783) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 704.

[1981] [Chemistry 460]

[1982]

[1983] Synthetic Example (1-203): Synthesis of Compound (1-1356)

[1984] The compound represented by formula (1-1356) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 692.

[1985] [Chemistry 461]

[1986]

[1987] Synthetic Example (1-204): Synthesis of Compound (1-1626)

[1988] The compound represented by formula (1-1626) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 560.

[1989] [Chemistry 462]

[1990]

[1991] Synthetic Example (1-205): Synthesis of Compound (1-1467)

[1992] The compound represented by formula (1-1467) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 508.

[1993] [Chemistry 463]

[1994]

[1995] Synthetic Example (1-206): Synthesis of Compound (1-1347)

[1996] The compound represented by formula (1-1347) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 588.

[1997] [Chemistry 464]

[1998]

[1999] Synthetic Example (1-207): Synthesis of Compound (1-1860)

[2000] The compound represented by formula (1-1860) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 572.

[2001] [Chemistry 465]

[2002]

[2003] Synthetic Example (1-208): Synthesis of Compound (1-1855)

[2004] The compound represented by formula (1-1855) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 520.

[2005] [Chemistry 466]

[2006]

[2007] Synthetic Example (1-209): Synthesis of Compound (1-2397)

[2008] The compound represented by formula (1-2397) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 560.

[2009] [Chemistry 467]

[2010]

[2011] Synthetic Example (1-210): Synthesis of Compound (1-2398)

[2012] The compound represented by formula (1-2398) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 508.

[2013] [Chemistry 468]

[2014]

[2015] Synthetic Example (1-211): Synthesis of Compound (1-4655)

[2016] Compound (1-4655) was synthesized by appropriately modifying the starting material compound used in the synthetic examples (1-56). EI-MS: m / z = 526.

[2017] [Chemistry 469]

[2018]

[2019] Synthetic Example (1-212): Synthesis of Compound (1-4660)

[2020] Compound (1-4660) was synthesized by appropriately modifying the starting material compound used in the synthetic examples (1-56). EI-MS: m / z = 592.

[2021] [Chemistry 470]

[2022]

[2023] Synthetic Example (1-213): Synthesis of Compound (1-2388)

[2024] The compound represented by formula (1-2388) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 613.

[2025] [Chemistry 471]

[2026]

[2027] Synthetic Example (1-214): Synthesis of Compound (1-4573)

[2028] The compound represented by formula (1-4573) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 601.

[2029] [Chemistry 472]

[2030]

[2031] Synthetic Example (1-215): Synthesis of Compound (1-4579)

[2032] Compound (1-4579) was synthesized by appropriately modifying the starting material compound used in the synthetic examples (1-56). EI-MS: m / z = 588.

[2033] [Chemistry 473]

[2034]

[2035] Synthetic Example (1-216): Synthesis of Compound (1-4510)

[2036] The compound represented by formula (1-4510) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 601.

[2037] [Chemistry 474]

[2038]

[2039] Synthetic Example (1-217): Synthesis of Compound (1-4701)

[2040] The compound represented by formula (1-4701) was synthesized using the same method as in synthetic example (1-187). EI-MS: m / z = 640.

[2041] [Chemistry 475]

[2042]

[2043] Synthetic Example (1-218): Synthesis of Compound (1-4688)

[2044] Compound (1-4688) was synthesized by appropriately modifying the starting material compound used in the synthetic examples (1-56). EI-MS: m / z = 631.

[2045] [Chemistry 476]

[2046]

[2047] Synthetic Example (1-219): Synthesis of Compound (1-4715)

[2048] Compound (1-4715) was synthesized by appropriately modifying the starti...

Claims

1. An organic electroluminescent element comprising a pair of electrodes and a light-emitting layer, the pair of electrodes comprising an anode and a cathode, the light-emitting layer disposed between the pair of electrodes, and the light-emitting layer comprising a host material and a polycyclic aromatic compound represented by the following formula (2) or a polymer of a plurality of polycyclic aromatic compounds having a structure represented by the following formula (2) as a dopant material, wherein the host material is an anthracene compound represented by the following formula (1), or a combination of two or more anthracene compounds represented by the following formula (1). In equation (1), Ar c It is a substituted aryl group or a substituted heteroaryl group. R c It is hydrogen, alkyl or cycloalkyl, Ar 11 Ar 12 Ar 13 Ar 14 Ar 15 Ar 16 Ar 17 and Ar 18 Any two of them are substituted aryl or substituted heteroaryl groups, and the other six are hydrogen, substituted alkyl, substituted cycloalkyl, substituted alkenyl, or substituted alkoxy groups. At least one hydrogen atom in the compound represented by formula (1) may be substituted by a halogen, a cyano group, or a deuterium. In equation (2), Rings A, B, and C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings can be substituted. X 1 and X 2 Each of the following can be independently represented as >O, >NR, >C(-R)2, >S, or >Se, wherein the R in >NR is a substituted aryl, substituted heteroaryl, substituted alkyl, or substituted cycloalkyl, and the R in >C(-R)2 is hydrogen, a substituted aryl, a substituted alkyl, or a substituted cycloalkyl. Furthermore, the R in >NR and / or the R in >C(-R)2 can be bonded to the A ring, the B ring, and / or the C ring via a linking group or a single bond. At least one of the aryl ring and heteroaryl ring in the compound represented by formula (2) or its polymer may be condensed from at least one cycloalkane, wherein at least one hydrogen atom in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-. At least one hydrogen atom in the compound or structure represented by formula (2) may be replaced by deuterium, cyano or halogen.

2. The organic electroluminescent element according to claim 1, wherein the polycyclic aromatic compound represented by formula (2) or a polymer of a plurality of polycyclic aromatic compounds having the structure represented by formula (2) is a polycyclic aromatic compound represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f) or a polymer of a polycyclic aromatic compound having the structure represented by a plurality of polycyclic aromatic compounds having the structure represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f), In equations (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f), R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 and R 11 Each of the following groups is independently hydrogen, aryl, heteroaryl, diarylamino, diheterarylamino, arylheterarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, wherein at least one hydrogen atom may be substituted by an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl group, R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 and R 11 The adjacent groups in the ring may bond to each other and together with ring a, ring b, or ring c to form an aryl ring or a heteroaryl ring. At least one hydrogen in the formed ring may be replaced by an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl group, where the two aryl groups may be bonded via a single bond or a linking group. At least one hydrogen in these groups may be replaced by an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl group. X X Each of the following can be independently >O, >S, >NR, or >C(-R)2, wherein the R in >NR is a substituted aryl, a substituted heteroaryl, a substituted alkyl, or a substituted cycloalkyl, and the R in >C(-R)2 can be independently hydrogen, an aryl group substituted by an alkyl or cycloalkyl group, a heteroaryl group substituted by an alkyl or cycloalkyl group, an alkyl, or a cycloalkyl. X 1 and X 2 Each of the following can be independently represented as >O, >NR, >C(-R)2, >S, or >Se, wherein the R in >NR is an aryl group of 6-12 carbons that can be substituted by an alkyl group of 1-6 carbons or a cycloalkyl group of 3-14 carbons, a heteroaryl group of 2-15 carbons that can be substituted by an alkyl group of 1-6 carbons or a cycloalkyl group of 3-14 carbons, or an alkyl group of 1-6 carbons or a cycloalkyl group of 3-14 carbons, and the R in >C(-R)2 is hydrogen, which can be substituted by an alkyl group of 1-6 carbons. Alternatively, the R of the >NR group may be an aryl group with 6 to 12 carbon atoms, an alkyl group with 1 to 6 carbon atoms, or a cycloalkyl group with 3 to 14 carbon atoms substituted with a cycloalkyl group. Furthermore, the R of the >NR group and / or the R of the >C(-R)2 group may be bonded to the a ring, the b ring, and / or the c ring via -O-, -S-, -C(-R)2-, or a single bond. The R of the -C(-R)2- group may be independently an alkyl group with 1 to 6 carbon atoms or a cycloalkyl group with 3 to 14 carbon atoms. At least one of the aryl and heteroaryl rings in the compounds or polymers represented by formulas (2-a), (2-b), (2-c), (2-d), (2-e), or (2-f) may be condensed from at least one cycloalkane, wherein at least one hydrogen atom in the cycloalkane may be substituted, and at least one -CH2- atom in the cycloalkane may be substituted with -O-. In the compounds or structures represented by formulas (2-a), (2-b), (2-c), (2-d), (2-e), or (2-f), at least one hydrogen atom may be substituted by a deuterium, cyano, or halogen. In the case of a polymer, it is a dimer or trimer having two or three structures represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f).

3. The organic electroluminescent element according to claim 2, wherein the compound represented by formula (2) is a polycyclic aromatic compound represented by formula (2-a) or formula (2-b) or a polymer of a plurality of polycyclic aromatic compounds having the structure represented by formula (2-a) or formula (2-b).

4. The organic electroluminescent element according to claim 3, wherein the compound represented by formula (2) is any one of the compounds represented by the following formulas. In the formula, Me is methyl, tBu is tert-butyl, tAm is tert-pentyl, and D is deuterium.

5. The organic electroluminescent element according to any one of claims 1 to 4, wherein the anthracene compound represented by formula (1) is an anthracene compound represented by formula (1A), formula (1B), formula (1C), formula (1D) or formula (1E). In equation (1A), equation (1B), equation (1C), equation (1D), or equation (1E), Ar c '、Ar 11 '、Ar 12 '、Ar 13 '、Ar 14 '、Ar 15 '、Ar 17 'and Ar 18 'Each group is independently phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthryl, fluorenyl, benzo[a]fluorenyl, hydroxyl, triphenylene, pyrene, or a group represented by formula (A), wherein at least one hydrogen atom in these groups may be substituted by phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthryl, fluorenyl, benzo[a]fluorenyl, hydroxyl, triphenylene, pyrene, or a group represented by formula (A). Here, when both hydrogen atoms of the methylene group in the fluorenyl and benzo[a]fluorenyl groups are substituted by phenyl groups, these phenyl groups may be bonded to each other by single bonds.' In the unbonded Ar c '、Ar 11 '、Ar 12 '、Ar 13 '、Ar 14 '、Ar 15 '、Ar 17 'or Ar 18 The carbon atoms on the anthracene ring can be bonded with methyl or tert-butyl groups to replace hydrogen. In the compounds represented by formulas (1A), (1B), (1C), (1D), or (1E), at least one hydrogen atom may be substituted by a halogen, a cyano group, or a deuterium. The base represented by formula (A) is the base obtained by removing a hydrogen atom from any position in formula (A). Indicates the location, In equation (A), Y is -O-, -S-, or >NR. 39 R 21 ~R 28 Each of the following is independently hydrogen, a substituted alkyl group, a substituted cycloalkyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, a substituted amino group, a halogen, a hydroxyl group, or a cyano group, R. 21 ~R 28 The adjacent groups can bond to each other to form a hydrocarbon ring, aryl ring, or heteroaryl ring. At least one hydrogen atom in the formed hydrocarbon ring, aryl ring, or heteroaryl ring can be substituted by a substituted alkyl group, a substituted cycloalkyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, a substituted amino group, a halogen group, a hydroxyl group, or a cyano group. 39 It is hydrogen or a substituted aryl group.

6. The organic electroluminescent element according to claim 5, wherein... The basis represented by equation (A) is any one of the bases represented by equations (A-1) to (A-14). The bases represented by formulas (A-1) to (A-14) are bases obtained by removing a hydrogen atom from any position in each of formulas (A-1) to (A-14). Indicates the location, In equations (A-1) to (A-14), Y is -O-, -S-, or >NR. 39 R 39 The group is hydrogen or aryl, and at least one hydrogen atom in the group represented by formulas (A-1) to (A-14) may be substituted by alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxyl, or cyano. 。 7. The organic electroluminescent element according to claim 5, wherein... Ar c '、Ar 11 '、Ar 12 '、Ar 13 '、Ar 14 '、Ar 15 '、Ar 17 'and Ar 18 Each group is independently represented by a group consisting of phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, or any of the groups represented by formulas (A-1) to (A-4), wherein at least one hydrogen atom in these groups may be substituted by a group represented by phenyl, biphenyl, naphthyl, phenanthryl, fluorenyl, or any of the groups represented by formulas (A-1) to (A-4). At least one hydrogen atom in the compound represented by formula (1A), formula (1B), formula (1C), formula (1D) or formula (1E) may be substituted with halogen, cyano or deuterium.

8. The organic electroluminescent element according to any one of claims 1 to 4, wherein Ar 14 and Ar 15 Ar is a substituted aryl group or a substituted heteroaryl group. 11 Ar 12 Ar 13 Ar 16 Ar 17 and Ar 18 Both are hydrogen.

9. The organic electroluminescent element according to claim 8, wherein Ar is selected as the organic electroluminescent element. c Ar 14 and Ar 15 At least one of the groups is a base containing anthracene rings.

10. The organic electroluminescent element according to claim 8, wherein Ar is selected from... c Ar 14 and Ar 15 The base represented by at least one inclusion expression (A') in the group formed, In formula (A'), R 21 ~R 28 Each of the following is independently hydrogen, a substituted alkyl group, a substituted cycloalkyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, a substituted amino group, a halogen, a hydroxyl group, or a cyano group, R. 21 ~R 28 The adjacent groups can bond with each other to form a hydrocarbon ring, aryl ring, or heteroaryl ring. At least one hydrogen in the formed hydrocarbon ring, aryl ring, or heteroaryl ring can be substituted by a substituted alkyl group, a substituted cycloalkyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, a substituted amino group, a halogen group, a hydroxyl group, or a cyano group.

11. The organic electroluminescent element according to claim 8, wherein at least one hydrogen atom in the compound represented by formula (1) is replaced by deuterium.

12. The organic electroluminescent element according to any one of claims 1 to 4, comprising an electron transport layer and / or an electron injection layer disposed between the cathode and the light-emitting layer, wherein at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzo[a]fluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, aryl nitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, hydroxyquinoline metal complexes, thiazole derivatives, benzo[a]thiazole derivatives, thiophene derivatives, and azoline derivatives.

13. The organic electroluminescent element according to claim 12, wherein the electron transport layer and / or electron injection layer further comprises at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals.

14. A display device comprising an organic electroluminescent element as claimed in any one of claims 1 to 13.

15. A lighting device comprising an organic electroluminescent element as claimed in any one of claims 1 to 13.

16. An anthracene compound represented by the following formula (1): In equation (1), Ar c Ar 14 and Ar 15 It is a substituted aryl group or a substituted heteroaryl group. R c It is hydrogen, alkyl or cycloalkyl, Ar 11 、Ar 12 、Ar 13 、Ar 16 、Ar 17 and Ar 18 are all hydrogen, Ar 14 and Ar 15 At least one of them is a group containing an anthracene ring. At least one hydrogen atom in the compound represented by formula (1) may be substituted by halogen, cyano or deuterium.

17. The anthracene compound according to claim 16, represented by the following formula (1Aa): In equation (1Aa), Ar c '、Ar 14 'and Ar 15 'Each group is independently represented by a phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, fluorenyl, benzo[a]fluorenyl, hydroxyl, triphenylene, pyrene, or any group represented by formulas (A-1) to (A-14), wherein at least one hydrogen atom in these groups may be substituted by a phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthrene, fluorenyl, benzo[a]fluorenyl, hydroxyl, triphenylene, pyrene, or any group represented by formulas (A-1) to (A-14). Here, when the hydrogen atoms of the methylene groups in the fluorenyl and benzo[a]fluorenyl groups are both substituted by phenyl groups, these phenyl groups can be bonded to each other by single bonds. In the unbonded Ar c '、Ar 14 'or Ar 15 The carbon atoms on the anthracene ring can be bonded with methyl or tert-butyl groups to replace hydrogen. Ar 14 'and Ar 15 At least one of them is a group containing an anthracene ring. In the compound represented by formula (1Aa), at least one hydrogen atom may be substituted by a halogen, a cyano group, or a deuterium group. The bases represented by formulas (A-1) to (A-14) are bases obtained by removing a hydrogen atom from any position in each of formulas (A-1) to (A-14). Indicates the location, In equations (A-1) to (A-14), Y is -O-, -S-, or >NR. 39 R 39 The group is hydrogen or aryl, and at least one hydrogen atom in the group represented by formulas (A-1) to (A-14) may be substituted by alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxyl, or cyano. in, At least one hydrogen atom in the compound represented by formula (1Aa) may be substituted by a halogen or a cyano group, and at least one hydrogen atom in the compound represented by formula (1Aa) may be substituted by a deuterium group.

18. The anthracene compound according to claim 17, wherein... , and Each group is independently represented by a phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, or any of the groups represented by formulas (A-1) to (A-4). and At least one of them is a group containing an anthracene ring, and at least one hydrogen of these groups may be substituted by a group represented by phenyl, naphthyl, phenanthryl, fluorenyl, or any of the groups represented by formulas (A-1) to (A-4).

19. The anthracene compound according to claim 17 or 18, wherein in formula (1Aa), at least the hydrogen atom bonded to the 10-position of the anthracene ring is replaced with deuterium.

20. An anthracene compound represented by any of the following formulas: In the formula, D represents deuterium.

21. An anthracene compound represented by any of the following formulas: In the formula, D represents deuterium.

22. An anthracene compound represented by any of the following formulas: 。 23. An anthracene compound represented by any of the following formulas: In the formula, D represents deuterium.

24. An anthracene compound represented by any of the following formulas: In the formula, D represents deuterium.

25. An anthracene compound represented by any of the following formulas: In the formula, Me represents methyl, tBu represents tert-butyl, and CyHex represents cyclohexyl.

26. An anthracene compound represented by any of the following formulas: In the formula, D represents deuterium.

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