Compound for organic electric element, organic electric element using same, and electronic device thereof

Abstract

The present invention provides: a compound represented by chemical formula 1; a method for recovering same; a material for an organic electric element, containing chemical formula 1 and chemical formula I; and an organic electric element comprising a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode. A compound of chemical formula 1 or a mixture of compounds represented by chemical formula 1 and chemical formula I is included in the organic layer, and thus the driving voltage of the organic electric element can be lowered and luminous efficiency and lifetime can be improved.

Description

Compounds for organic electric devices, organic electric devices using the same, and electronic devices thereof

[0001] The present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.

[0002] In general, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic electrical devices utilizing organic light emission typically have a structure that includes an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure made of different materials to increase the efficiency and stability of the organic electrical device, and may consist of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0003] Materials used as organic layers in organic electronic devices can be classified according to their function into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials. Furthermore, the light-emitting materials can be classified into high-molecular and low-molecular types based on molecular weight, and into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons based on the light emission mechanism. Additionally, light-emitting materials can be classified according to their emission color into blue, green, and red light-emitting materials, as well as yellow and orange light-emitting materials necessary to achieve better natural colors.

[0004] Meanwhile, when only a single material is used as a light-emitting material, intermolecular interactions cause the maximum emission wavelength to shift to a longer wavelength, resulting in reduced color purity or decreased device efficiency due to light attenuation effects. Therefore, a host / dopant system can be used as a light-emitting material to increase color purity and luminous efficiency through energy transfer. The principle is that when a small amount of a dopant, which has a smaller energy band gap than the host forming the light-emitting layer, is mixed into the light-emitting layer, excitons generated in the light-emitting layer are transported to the dopant, emitting high-efficiency light. At this time, since the wavelength of the host shifts to the wavelength range of the dopant, light of the desired wavelength can be obtained depending on the type of dopant used.

[0005] Currently, the portable display market is trending toward larger displays, which requires higher power consumption than that of conventional portable displays. Consequently, for portable displays that rely on the limited power source of batteries, power consumption has become a critical factor, and issues regarding efficiency and lifespan must also be resolved.

[0006] Efficiency, lifespan, and driving voltage are interrelated; as efficiency increases, the driving voltage relatively decreases. Consequently, a lower driving voltage reduces the crystallization of organic materials caused by Joule heating during operation, which in turn tends to extend lifespan. However, simply improving the organic layers does not guarantee maximum efficiency. This is because both long lifespan and high efficiency can be achieved simultaneously when the energy levels and T1 values ​​between the organic layers, along with the intrinsic properties of the materials (such as mobility and interfacial characteristics), form an optimal combination.

[0007] Therefore, there is a need to develop light-emitting materials that possess high thermal stability and can efficiently achieve charge balance within the emissive layer. In other words, to fully realize the excellent characteristics of organic electronic devices, it is essential that the materials constituting the organic layer within the device—such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials—be supported by stable and efficient materials; among these, the development of host materials for the emissive layer is particularly necessary.

[0008] The present invention aims to provide a compound for an organic electric device capable of lowering the driving voltage of the device and improving the luminous efficiency and lifespan of the device, an organic electric device using the same, and an electronic device thereof.

[0009] In one aspect, the present invention provides a compound represented by the following chemical formula 1.

[0010] <Chemical Formula 1>

[0011]

[0012] In another aspect, the present invention provides a material for an organic electric device containing a compound represented by the above chemical formula 1 and the following chemical formula I.

[0013] <Chemical Formula I>

[0014]

[0015] In another aspect, the present invention provides an organic electric device and an electronic device thereof, comprising a material for an organic electric device that includes a compound of Formula 1 or contains a compound of Formula 1 and Formula I.

[0016] In another aspect, the present invention provides a method for recovering a compound represented by the above chemical formula 1.

[0017] By using a compound according to an embodiment of the present invention as a material for an organic electric device, the driving voltage of the device can be lowered, and the luminous efficiency and lifespan can be improved.

[0018] FIGS. 1 to 3 are exemplary diagrams of an organic electroluminescent device according to an embodiment of the present invention.

[0019] [Explanation of the symbol]

[0020] 100, 200, 300: Organic electric device 110: First electrode

[0021] 120: Hole Injection Layer 130: Hole Transport Layer

[0022] 140: Emissive layer 150: Electron transport layer

[0023] 160: Electron injection layer 170: Second electrode

[0024] 180: Light efficiency improvement layer 210: Buffer layer

[0025] 220: Light-emitting auxiliary layer 320: First hole injection layer

[0026] 330: 1st hole transport layer 340: 1st light-emitting layer

[0027] 350: First electron transport layer 360: First charge generation layer

[0028] 361: Second charge generation layer 420: Second hole injection layer

[0029] 430: Second hole transport layer 440: Second light-emitting layer

[0030] 450: Second electron transport layer CGL: Charge generation layer

[0031] ST1: 1st Stack ST2: 2nd Stack

[0032] In this specification, "aryl group," "arylene group," and "aromatic ring" refer to hydrocarbon aromatic rings, and unless otherwise stated, each has 6 to 60 carbon atoms, but is not limited thereto. In the present invention, an aryl group or an arylene group includes a single ring, a polycyclic ring, and a condensed ring, etc.

[0033] In addition, in this specification, aryl groups or arylene groups are, for example, C6 to C 60 , C6~C 30 , C6~C 29 , C6~C 28 , C6~C 27 , C6~C 26 , C6~C 25 , C6~C 24 , C6~C 23 , C6~C 22 , C6~C 21 , C6~C 20 , C6~C 19 , C6~C 18 , C6~C 17 , C6~C 16 , C6~C 15 , C6~C 14 , C6~C 13 , C6~C 12 , C6~C 11 , C6~C 10 , C6, C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 It may be an aryl group or an arylene group, specifically phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, benzophenanthrene, triphenylene, chrysene, or a combination thereof, in particular phenyl, naphthyl, phenanthrene, or a combination thereof.

[0034] In this specification, "fluorenyl group" refers to a substituted or unsubstituted fluorenyl group, and "fluorenylene group" refers to a substituted or unsubstituted fluorenylene group. The fluorenyl group or fluorenylene group used in the present invention includes a spiro compound formed by R and R' being bonded to each other in the following structure, and also includes a compound in which adjacent R" are bonded to each other to form a ring. "Substituted fluorenyl group" and "substituted fluorenylene group" mean that at least one of R, R', and R" in the following structure is a substituent other than hydrogen, and in the chemical formula below, R" may be 1 to 8. In this specification, regardless of the valence, the fluorenyl group, fluorenylene group, etc. may be described as a fluoren group or fluorene.

[0035] In addition, the fluorene group may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[b]fluorene-11,9'-fluorene], benzo[b]fluorene, 11,11-diphenyl-11H-benzo[b]fluorene, 9-(naphthalene-2-yl)9-phenyl-9H-fluorene, etc.

[0036] In addition, when one R" is substituted in the following chemical formula, depending on the position where R" is substituted, it can be 1-fluorene, 2-fluorene, 3-fluorene, or 4-fluorene, and when two R" are substituted, the two R" can be substituted at positions 2 and 5, 2 and 7, 4 and 5, 4 and 7, etc.

[0037]

[0038] In this specification, "spyro compound" refers to a compound having a "spyro linkage," where a spyro linkage means a connection formed by two rings sharing only one atom. At this time, the atom shared by the two rings is called a "spyro atom," and depending on the number of spyro atoms contained in a compound, they are respectively called "monospyro-," "diespyro-," and "trispyro-" compounds. For example, when R and R" in the above fluorene structural formula bond to each other to form a ring, a spiro compound may be formed, and the formed ring may be a ring of 5, 6, 10, 13, 14, 17, 18, 21, 22 atoms including the spiro atom, and in particular, rings such as fluorene, benzofluorene, dibenzofluorene, xanthen, and thioxanthen may be formed. For example, when R and R" bond to each other to form a fluorene ring, a 9,9'-spirobifluorene compound is formed.

[0039] In this specification, "heterocyclic group" includes not only aromatic heterocyclic groups such as "heteroaryl groups" or "heteroarylene groups" but also non-aromatic heterocyclic groups, and unless otherwise stated, means a ring having 2 to 60 carbon atoms containing one or more heteroatoms, but is not limited thereto. Additionally, "heteroatom" refers to an element other than carbon, such as N, O, S, P, or Si, and may include heteroatom groups such as SO2, P=O, etc., as in the following compounds, instead of carbon forming the ring.

[0040]

[0041] In addition, heterocyclic rings include monocyclic, polycyclic, or condensed rings containing heteroatoms, and in the case of condensed rings, if at least one of the condensed rings is a ring containing a heteroatom, it is defined as a heterocyclic ring. For example, heterocyclic rings such as furan, dihydrofuran, thiophene, pyrrole, pyridine, etc., and aromatic rings such as benzene, naphthalene, phenanthrene, etc., or aliphatic rings such as cyclopentane, cyclohexane, etc., are condensed to form a condensed ring, and in the case of a spiro compound, at least one ring contains a heteroatom, it is also a heterocyclic ring.

[0042] In addition, in this specification, heterocycles are, for example, C2~C 60 , C2~C 30 , C2~C 29 , C2~C 28 , C2~C 27 , C2~C 26 , C2~C 25 , C2~C 24 , C2~C 23 , C2~C 22 , C2~C 21 , C2~C 20 , C2~C 19 , C2~C 18 , C2~C 17 , C2~C 16 , C2~C 15 , C2~C 14 , C2~C 13 , C2~C 12 , C2~C 11 , C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C19 , C 20 , C 21 , C 22 , C 23 , C 24 , C 25 , C 26 , C 27 , C 28 , C 29 It may be a heterocyclic group such as pyridine, pyrimidine, pyrazine, pyridazine, triazine, pyrrole, indole, phenyl-indole, benzodole, phenyl-benzodole, pyrazinoindole, quinoline, isoquinoline, benzoquinoline, pyridoquinoline, quinazoline, benzoquinazoline, dibenzoquinazoline, phenantroquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, furan, benzoffuran, naphthobenzofuran, dibenzofuran, dynaphthofuran, phenantrobenzofuran, thiophene, benzothiophen, dibenzothiophen, naphthobenzothiophen, dynaphthiophen, phenantrobenzothiophen, carbazole, phenyl-carbazole, benzocarbazole, Phenyl-benzocarbazole, naphthyl-benzocarbazole, dibenzocarbazole, indolocarbazole, benzopuropyridine, benzothienopyridine, benzopuropyridine, benzothienopyrimidine, benzothienopyrazine, benzopuropyrazine, benzimidazole, benzothiazole, benzocilol, dibenzocilol, phenanthroline, dihydro-phenylphenazine, 10-phenyl-10H-phenoxazine, phenoxazine, phenothiazine, dibenzodibenzodioxin, cyanthrene, oxazole, benzoxazole, naphthoxazole, phenanthrooxazole, dibenzothienobenzoxazole, dibenzopurobenzoxazole, 9,9-dimethyl-9H-xanthen, It may be 9,9-dimethyl-9H-thioxanthen, dihydrodimethylphenylacridine, spiro[fluorene-9,9'-xanthen], etc.

[0043] In this specification, "aliphatic ring" refers to a cyclic hydrocarbon excluding aromatic hydrocarbons, and includes single rings, polycyclic rings, condensed rings, spiro compounds, etc. Unless otherwise stated, it refers to a ring having 3 to 60 carbon atoms, but is not limited thereto. In particular, in this specification, an aliphatic ring (group) is defined as a hydrocarbon ring that does not contain an aromatic ring. Accordingly, not only saturated hydrocarbon rings such as cycloalkyl groups, but also cases where there is one or more double bonds within the ring are considered to correspond to an aliphatic ring if they are not aromatic hydrocarbons.

[0044] In addition, in this specification, aliphatic rings are, for example, C3~C 60 , C3~C 30 , C3~C 29 , C3~C 28 , C3~C 27 , C3~C 26 , C3~C 25 , C3~C 24 , C3~C 23 , C3~C 22 , C3~C 21 , C3~C 20 , C3~C 19 , C3~C 18 , C3~C 17 , C3~C 16 , C3~C 15 , C3~C 14 , C3~C 13 , C3~C 12 , C3~C 11 , C3~C 10 , C3~C8, C3~C6, C6, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18It may be an aliphatic ring. In addition, the aliphatic ring may be a cycloalkyl, such as cyclobutane, cyclopentane, cyclohexane, cyclohexene, bicycloheptane, adamantyl, etc.

[0045] In this specification, "fusion ring(group)" or "condensation ring(group)" means a ring in which an aliphatic ring and an aromatic hydrocarbon (aromatic ring or aryl ring) are condensed together unless otherwise described, and means a ring in which an aliphatic ring having 3 to 60 carbon atoms and an aromatic hydrocarbon having 6 to 60 carbon atoms are condensed together unless otherwise described.

[0046] In this specification, "alkyl group" includes normal alkyl groups, branched alkyl groups, etc. The said alkyl group is, for example, C1 to C 20 , C1~C 10 It may be an alkyl group such as C1~C9, C1~C8, C1~C7, C1~C6, C1~C5, C1~C4, C1~C3, C1~C2, C1, C2, C3, C4, C5, C6, C7, etc., and may be, for example, a methyl group, ethyl group, propyl group, isopropyl group, butyl group, t-butyl group, pentyl group, etc., and the hydrogen of the alkyl group may be replaced with deuterium.

[0047] In this specification, the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc., which are exemplified as examples of each symbol and its substituent, may be written as the 'name of the group reflecting the valence,' or it may be written as the 'name of the parent compound.' For example, in the case of 'phenanthrene,' a type of aryl group, the group name may be written by distinguishing the valence, such as 'phenanthrile' for the monovalent group and 'phenanthrillene' for the divalent group, but it may also be written as the parent compound name 'phenanthrene' regardless of the valence. Similarly, in the case of pyrimidine, it may be written as 'pyrimidine' regardless of the valence, or it may be written as the 'name of the group' corresponding to the valence, such as pyrimidinyl group for monovalent and pyrimidinyllene for divalent.

[0048] In addition, when describing compound names or substituent names in this specification, numbers or alphabets indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidine may be described as pyridopyrimidine, benzofuro[2,3-d]pyrimidine as benzofuropyrimidine, 9,9-dimethyl-9H-fluorene as dimethylfluorene, etc. Accordingly, both benzo[g]quinoxaline and benzo[f]quinoxaline may be described as benzoquinoxaline.

[0049] In addition, unless explicitly stated otherwise, the chemical formulas used in the present invention are applied identically to the definitions of substituents by the definitions of the indices of the following chemical formulas.

[0050]

[0051] Here, if a is an integer of 0, the substituent R 1 ≡ indicates absence; that is, when a is 0, it means that hydrogen is bonded to all carbons forming the benzene ring, in which case the chemical formula or compound can be written without indicating the hydrogen bonded to the carbons. Additionally, when a is an integer of 1, one substituent R 1 It bonds to any one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it can bond, for example, as follows; when a is an integer of 4 to 6, it bonds to the carbons of the benzene ring in a similar manner; and when a is an integer greater than or equal to 2, R 1 They may be the same or different from each other.

[0052]

[0053] Additionally, in this specification, the term "ring" refers to an aryl ring, a heteroaryl ring, a fluorene ring, an aliphatic ring, a fused ring, etc., and terms such as "number-ring," "number-condensed ring," or "number-fused ring" refer to a form in which rings corresponding to the number are fused together, and "number-ring" may refer to the form of a ring. For example, naphthalene corresponds to a 2-ring, a 2-condensed ring, or a 2-fused ring; anthracene corresponds to a 3-ring, a 3-condensed ring, or a 3-fused ring; thiophene or furan corresponds to a 5-membered heteroring; and benzene or pyridine corresponds to a 6-membered aromatic ring.

[0054] In addition, in this specification, the rings formed by combining adjacent groups are C6~C 60 Aromatic ring; fluorene group; C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic ring of; C3~C 60 aliphatic ring of; and C3~C 60 The aliphatic ring and C6~C 60 The aromatic ring can be selected from a group of fused rings. Here, the aromatic ring can be an aryl ring, and the heteroring can include a heteroaryl ring.

[0055] In this specification, the term "neighboring groups" refers to, using the following chemical formula as an example, not only R1 and R2, R2 and R3, R3 and R4, and R5 and R6, but also R7 and R8 sharing a single carbon, and may also include substituents bonded to ring constituent elements (such as carbon or nitrogen) that are not immediately adjacent, such as R1 and R7, R1 and R8, or R4 and R5. That is, if there are substituents on ring constituent elements such as immediately adjacent carbons or nitrogen, these may be neighboring groups; however, if no substituents are bonded to ring constituent elements at immediately adjacent positions, the substituents bonded to the next ring constituent element may be neighboring groups, and substituents bonded to the same ring constituent carbon may also be considered neighboring groups. In the following chemical formula, when substituents bonded to the same carbon, such as R7 and R8, bond to each other to form a ring, a compound containing a spiro moiety may be formed.

[0056]

[0057] Additionally, in this specification, the expression "neighboring units may combine to form a ring" is used with the same meaning as "neighboring units selectively combine to form a ring," and refers to the case where at least one pair of neighboring units combine to form a ring.

[0058] In addition, in this specification, the phrase "neighboring groups can combine with each other to form a ring" means that neighboring groups can consequently form a ring, and R 1 and R 2 It is not assumed that the substituent contains an unsaturated bond, such as an alkenyl group or an alkyneyl group.

[0059] When adjacent groups combine to form a ring, the ring is C6~C 60 Aromatic ring (aryl ring); fluorene group; C3~C 60an aliphatic ring of; C2~C comprising at least one heteroatom among O, N, S, Si, and P. 60 heterocyclic; and C3~C 60 The aliphatic ring and C6~C 60 It can be selected from a group consisting of fused rings of aromatic rings.

[0060] When adjacent groups combine to form an aromatic ring (aryl ring), the said aromatic ring is, for example, C6~C 20 , C6~C 18 , C6~C 16 , C6~C 14 , C6~C 13 , C6~C 12 , C6~C 10 , C6, C 10 , C 12 , C 14 , C 15 , C 16 , C 18 It may be an aromatic ring, specifically, benzene, naphthalene, anthracene, phenanthrene, pyrene, triphenylene, etc.

[0061] In addition, in this specification, substituents such as aryl groups, arylene groups, fluorenyl groups, fluorenyl groups, heterocyclic groups, aliphatic cyclic groups, fused cyclic groups, alkyl groups, alkenyl groups, alkyneyl groups, alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, etc., and rings formed by the bonding of adjacent groups are each deuterium; halogen; C1-C 20 alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; C1-C 20 alkoxy group of; C6-C 30 aryloxy group of; C1-C 20 alkyl group of; C2-C 20 alkene diary; C2-C 20 Alkin's Diary; C6-C 30aryl group of; C6-C substituted with deuterium 30 aryl group of; C3-C 30 Aliphatic ring; C6-C 30 The aromatic ring and C3-C 30 A fused ring of an aliphatic ring; and a C2-C comprising at least one heteroatom among O, N, S, Si, and P. 30 It can be substituted with one or more substituents selected from a group of heterocyclic rings, and adjacent substituents can bond to each other to form a ring, and the hydrogen of the substituents can be replaced with deuterium.

[0062] In addition, in this specification, when at least one of the aryl group, arylene group, fluorenyl group, fluorenyllene group, heterocyclic group, aliphatic cyclic group, fused cyclic group, alkyl group, alkenyl group, alkyneyl group, alkoxy group, aryloxy group, alkylthio group, arylthio group, or a ring formed by the bonding of adjacent groups is substituted with an aryl group, said aryl group is, for example, C6 to C 30 , C6~C 29 , C6~C 28 , C6~C 27 , C6~C 26 , C6~C 25 , C6~C 24 , C6~C 23 , C6~C 22 , C6~C 21 , C6~C 20 , C6~C 19 , C6~C 18 , C6~C 17 , C6~C 16 , C6~C 15 , C6~C 14 , C6~C 13 , C6~C 12 , C6~C 11 , C6~C 10 , C6, C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C18 It may be an aryl group such as, specifically, phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, benzophenanthrene, triphenylene, chrysene, or a combination thereof, in particular phenyl, naphthyl, or a combination thereof.

[0063] In addition, when at least one of the rings formed by the bonding of adjacent groups—such as an aryl group, an arylene group, a fluorenyl group, a fluorenyl group, a heterocyclic group, an aliphatic ring, a fused ring, an alkyl group, an alkenyl group, an alkyneyl group, an alkoxy group, an aryloxy group, an alkylthio group, or an arylthio group—is substituted with a heterocyclic group, the heterocyclic group is, for example, C2~C 30 , C2~C 29 , C2~C 28 , C2~C 27 , C2~C 26 , C2~C 25 , C2~C 24 , C2~C 23 , C2~C 22 , C2~C 21 , C2~C 20 , C2~C 19 , C2~C 18 , C2~C 17 , C2~C 16 , C2~C 15 , C2~C 14 , C2~C 13 , C2~C 12 , C2~C 11 , C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 It can be a heterocyclic ring.

[0064] In addition, when at least one of the rings formed by the bonding of adjacent groups—such as an aryl group, an arylene group, a fluorenyl group, a fluorenyl group, a heterocyclic group, an aliphatic group, a fused group, an alkyl group, an alkenyl group, an alkyneyl group, an alkoxy group, an aryloxy group, an alkylthio group, or an arylthio group—is substituted with an aliphatic group, the aliphatic group is, for example, C3~C 30 , C3~C 29 , C3~C 28 , C3~C 27 , C3~C 26 , C3~C 25 , C3~C 24 , C3~C 23 , C3~C 22 , C3~C 21 , C3~C 20 , C3~C 19 , C3~C 18 , C3~C 17 , C3~C 16 , C3~C 15 , C3~C 14 , C3~C 13 , C3~C 12 , C3~C 11 , C3~C 10 , C3~C8, C3~C6, C6, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 It could be a fatty ring on the back.

[0065] In addition, when at least one of the rings formed by the bonding of adjacent groups is substituted with an alkyl group, such as an aryl group, an arylene group, a fluorenyl group, a fluorenyl group, a heterocyclic group, an aliphatic cyclic group, a fused cyclic group, an alkyl group, an alkenyl group, an alkyneyl group, an alkoxy group, an aryloxy group, an alkylthio group, or an arylthio group, the alkyl group is, for example, C1 to C 20 , C1~C 10It may be an alkyl group such as C1~C9, C1~C8, C1~C7, C1~C6, C1~C5, C1~C4, C1~C3, C1~C2, C1, C2, C3, C4, C5, C6, C7, etc., and may be, for example, a methyl group, ethyl group, propyl group, isopropyl group, butyl group, t-butyl group, pentyl group, etc., and the hydrogen of the alkyl group may be replaced with deuterium.

[0066] Unless otherwise explained in this specification, the mark "*" or " " indicates the connecting part.

[0067] Hereinafter, a stacked structure of an organic electric device containing a compound of the present invention will be described with reference to FIGS. 1 to 3.

[0068] It should be noted that when assigning reference numerals to the components of each drawing, the same components are assigned the same reference numeral whenever possible, even if they are shown in different drawings. Furthermore, in describing the present invention, if it is determined that a detailed description of related known components or functions could obscure the essence of the invention, such detailed description is omitted.

[0069] In describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc., may be used. These terms are intended merely to distinguish the components from other components, and the nature, order, or sequence of the components is not limited by these terms. Where it is stated that a component is "connected," "combined," or "joined" to another component, it should be understood that the component may be directly connected or joined to the other component, but that another component may also be "connected," "combined," or "joined" between each component.

[0070] Furthermore, when it is stated that a component, such as a layer, membrane, region, or plate, is "on" or "on" another component, it should be understood that this includes not only the case where it is "directly on" another component, but also the case where there is another component in between. Conversely, when it is stated that a component is "directly on" another part, it should be understood that this means there is no other part in between.

[0071] FIGS. 1 to 3 are exemplary diagrams of an organic electric device according to an embodiment of the present invention.

[0072] Referring to FIG. 1, an organic electric device (100) according to one embodiment of the present invention includes a first electrode (110) formed on a substrate (not shown), a second electrode (170), and an organic layer formed between the first electrode (110) and the second electrode (170), and may also include an inorganic layer between the first electrode (110) and the second electrode (120).

[0073] For example, the first electrode (110) may be an anode (positive electrode) and the second electrode (170) may be a cathode (negative electrode), and in the case of an invert type, the first electrode may be a cathode and the second electrode may be an anode.

[0074] The above organic layer refers to a layer containing at least one organic material. For example, the organic layer may include a hole injection layer (120), a hole transport layer (130), a light-emitting layer (140), an electron transport layer (150), and an electron injection layer (160). However, the electron injection layer (160) may be an inorganic layer that does not contain organic material.

[0075] Specifically, a hole injection layer (120), a hole transport layer (130), a light-emitting layer (140), an electron transport layer (150), and an electron injection layer (160) can be sequentially formed on the first electrode (110).

[0076] Preferably, a light efficiency improvement layer (180) may be formed on one side of the first electrode (110) or the second electrode (170) that does not come into contact with an organic layer or an inorganic layer, and when the light efficiency improvement layer (180) is formed, the light efficiency of the organic electric device may be improved.

[0077] For example, a light efficiency improvement layer (180) may be formed on the second electrode (170). In the case of a top-emission organic light-emitting device, the formation of the light efficiency improvement layer (180) can reduce optical energy loss caused by SPPs (surface plasmon polaritons) at the second electrode (170), and in the case of a bottom-emission organic light-emitting device, the light efficiency improvement layer (180) can perform a buffering role for the second electrode (170).

[0078] A buffer layer (210) or a light-emitting auxiliary layer (220) may be further formed between the hole transport layer (130) and the light-emitting layer (140), and this will be explained with reference to FIG. 2.

[0079] Referring to FIG. 2, an organic electric device (200) according to another embodiment of the present invention may include a hole injection layer (120), a hole transport layer (130), a buffer layer (210), a light-emitting auxiliary layer (220), a light-emitting layer (140), an electron transport layer (150), an electron injection layer (160), and a second electrode (170) formed sequentially on a first electrode (110), and a light efficiency improvement layer (180) may be formed on the second electrode.

[0080] Although not shown in FIG. 2, an electron transport assist layer may be further formed between the light-emitting layer (140) and the electron transport layer (150).

[0081] In addition, according to another embodiment of the present invention, the organic layer may be in the form of a plurality of stacks including a hole transport layer, a light-emitting layer, and an electron transport layer. This will be explained with reference to FIG. 3.

[0082] Referring to FIG. 3, in another embodiment of the present invention, an organic electric device (300) may have two or more sets of stacks (ST1, ST2) of organic layers formed in multiple layers between a first electrode (110) and a second electrode (170), and a charge generating layer (CGL) may be formed between the stacks of organic layers.

[0083] Specifically, an organic electric device according to one embodiment of the present invention may include a first electrode (110), a first stack (ST1), a charge generation layer (CGL), a second stack (ST2), a second electrode (170), and a light efficiency improvement layer (180).

[0084] The first stack (ST1) is an organic layer formed on the first electrode (110), which may include a first hole injection layer (320), a first hole transport layer (330), a first light-emitting layer (340), and a first electron transport layer (350), and the second stack (ST2) may include a second hole injection layer (420), a second hole transport layer (430), a second light-emitting layer (440), and a second electron transport layer (450). Thus, the first stack and the second stack may be organic layers having the same stacking structure, but they may also be organic layers having different stacking structures.

[0085] A charge generation layer (CGL) may be formed between the first stack (ST1) and the second stack (ST2). The charge generation layer (CGL) may include a first charge generation layer (360) and a second charge generation layer (361). This charge generation layer (CGL) is formed between the first light-emitting layer (340) and the second light-emitting layer (440) to increase the current efficiency generated in each light-emitting layer and to facilitate the smooth distribution of charge.

[0086] The first light-emitting layer (340) may include a light-emitting material comprising a blue fluorescent dopant in a blue host, and the second light-emitting layer (440) may include a material doped with a greenish yellow dopant and a red dopant in a green host, but the materials of the first light-emitting layer (340) and the second light-emitting layer (440) according to the embodiment of the present invention are not limited thereto.

[0087] In FIG. 3, n can be an integer from 1 to 5, and when n is 2, a charge generation layer (CGL) and a third stack can be additionally stacked on the second stack (ST2).

[0088] As shown in Fig. 3, when multiple light-emitting layers are formed by a multilayer stack structure, it is possible to manufacture an organic electroluminescent device that emits white light through the mixing effect of light emitted from each light-emitting layer, as well as to manufacture an organic electroluminescent device that emits light of various colors.

[0089] A compound represented by Formula 1 of the present invention or a mixture of a compound of Formula 1 and a compound of Formula I may be included in an organic layer. For example, a compound represented by Formula 1 of the present invention or a mixture of a compound of Formula 1 and a compound of Formula I may be used as a material for a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer (210), a light-emitting auxiliary layer (220), an electron transport layer (150, 350, 450), a light-emitting layer (140, 340, 440), or a light efficiency improvement layer (180), but preferably may be used as a host for a light-emitting layer (140, 340, 440).

[0090] Even with identical or similar cores, the band gap, electrical properties, and interfacial properties can vary depending on which substituent is attached at which location; therefore, research on the selection of cores and the combination of sub-substituents attached thereto is necessary. In particular, long lifespan and high efficiency can be achieved simultaneously when the energy levels and T1 values ​​between each organic layer, along with the intrinsic properties of the material (mobility, interfacial properties, etc.), form an optimal combination.

[0091] Accordingly, in the present invention, by using a compound represented by Formula 1 or a mixture of the compound of Formula 1 and the compound of Formula I as a host for the light-emitting layer (140, 340, 440), the energy level and T1 value between each organic layer, and the intrinsic properties of the material (mobility, interfacial properties, etc.) can be optimized to simultaneously improve the lifespan and efficiency of the organic electric device.

[0092] An organic electroluminescent device according to one embodiment of the present invention may be manufactured using various deposition methods. It may be manufactured using deposition methods such as PVD or CVD. For example, it may be manufactured by forming an anode (110) by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, forming an organic layer including a hole injection layer (120), a hole transport layer (130), a light-emitting layer (140), an electron transport layer (150), and an electron injection layer (160) on the anode, and then depositing a material that can be used as a cathode (170) on the anode. Additionally, a light-emitting auxiliary layer (220) may be further formed between the hole transport layer (130) and the light-emitting layer (140), and an electron transport auxiliary layer (not shown) may be further formed between the light-emitting layer (140) and the electron transport layer (150), or it may be formed in a stack structure as described above.

[0093] In addition, the organic layer can be manufactured with fewer layers by using various polymer materials and by a solution process or solvent process other than a deposition method, such as a spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blading process, screen printing process, or thermal transfer method. Since the organic layer according to the present invention can be formed in various ways, the scope of the rights of the present invention is not limited by the method of formation.

[0094] An organic electric device according to one embodiment of the present invention may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0095] In addition, an organic electric device according to one embodiment of the present invention may be selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photosensitive material, an organic transistor, a device for monochromatic lighting, and a device for a quantum dot display.

[0096] Another embodiment of the present invention may include a display device comprising the organic electric element of the present invention described above, and an electronic device comprising a control unit that controls the display device. In this case, the electronic device may be a current or future wired or wireless communication terminal and includes all electronic devices such as mobile communication terminals such as mobile phones, navigation systems, game consoles, various TVs, and various computers.

[0097] Hereinafter, a compound according to one aspect of the present invention will be described.

[0098] A compound according to one aspect of the present invention is represented by the following chemical formula 1.

[0099] <Chemical Formula 1>

[0100]

[0101] <Chemical Formula A> <Chemical Formula B>

[0102]

[0103] In the above chemical formula 1, each symbol is defined as follows.

[0104] Ar a is chemical formula A or C6~C 60 It is an aryl group. In chemical formula A, * represents the bonding site. Therefore, the C ring is bonded to the nitrogen of the amine group through *.

[0105] Ar b is chemical formula B, and in chemical formula B, * represents the binding site.

[0106] X is NR 5 , O or S, and Y is O or S.

[0107] The C ring and the D ring are C6~C, respectively. 60 an aromatic ring; or a C2~C group comprising at least one heteroatom among O, N, S, Si, and P. 60 It is a heterocyclic ring, and the C ring and D ring each have one or more identical or distinct R 4 It can be substituted with. The C ring and D ring can be, for example, benzene, naphthalene, phenanthrene, triphenylene, benzothiophene, benzofuran, dibenzofuran, dibenzothiophene, carbazole, etc.

[0108] Therefore, Ar a If the chemical formula is A, Ar a It may be, for example, dibenzofuran, naphthobenzofuran, dynaphthofuran, phenantrobenzofuran, dibenzothiophen, naphthobenzothiophen, dynaphthiophen, phenantrobenzothiophen, carbazole, phenyl-carbazole, benzocarbazole, phenyl-benzocarbazole, naphthyl-benzocarbazole, dibenzocarbazole, indolocarbazole, benzothienopyrimidine, benzofuropyrimidine, benzothienopyrazine, benzofuropyrazine, etc.

[0109] Ar 1 C6~C 60 aryl group of; or C2~C comprising at least one heteroatom among O, N, S, Si and P 60 It is a heterocyclic ring.

[0110] L 1 is a single bond; C6~C 60 arylene group of; and C2~C comprising at least one heteroatom among O, N, S, Si and P. 60 It is selected from a group consisting of heterocycles.

[0111] R 1 It is hydrogen or deuterium.

[0112] R 2 to R 4 They are independently hydrogen; deuterium; halogen; cyano group; C6~C 60 aryl group of; C2~C comprising at least one heteroatom among O, N, S, Si, and P 60 The heterocyclic ring of; C3~C 60 aliphatic ring; C6~C 60 The aromatic ring and C3~C 60 Fusion ring of the aliphatic ring; C1~C 20 alkyl group of; C2~C 20 The Alken Diary of; C2~C 20 Alkin's Diary; C1~C 20 alkoxy groups; and C6~C 60 It is selected from the group consisting of aryloxy groups. Neighboring R 2 R together or adjacent 3 Cases where they combine with each other to form a ring are excluded.

[0113] R 5 is C6~C 60 aryl group of; C2~C comprising at least one heteroatom among O, N, S, Si, and P 60 The heterocyclic ring of; C3~C 60 aliphatic ring of; and C6~C 60 The aromatic ring and C3~C 60 It is selected from a group consisting of fused rings of aliphatic rings.

[0114] a is an integer from 0 to 6, b is an integer from 0 to 3, and c is an integer from 0 to 4, and if they are integers greater than or equal to 2, multiple R 1Each or multiple R 3 Each is either the same or different from the others.

[0115] Neighboring R 2 Together, neighboring R 3 Since cases where they combine with each other to form a ring are excluded, chemical formula B may be substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, etc.

[0116] However, the above Ar a , Ar 1 , R 2 to R 5 If it is Arilgi, or L 1 In the case of this arylene group, the arylene group and the arylene group are one or more single rings or condensed rings consisting only of six-membered rings, and in the case where the C ring and D ring are aromatic rings, the aromatic ring is one single ring or condensed ring consisting only of six-membered rings.

[0117] Ar a , Ar 1 , R 2 to R 5 At least one of them is an aryl group, or L 1 In the case where this is an arylene group, the above aryl group or arylene group is, for example, C6~C 60 , C6~C 30 , C6~C 29 , C6~C 28 , C6~C 27 , C6~C 26 , C6~C 25 , C6~C 24 , C6~C 23 , C6~C 22 , C6~C 21 , C6~C 20 , C6~C 19 , C6~C 18 , C6~C 17 , C6~C 16 , C6~C 15 , C6~C 14 , C6~C 13 , C6~C 10 , C6, C 10 , C13 , C 14 , C 16 , C 17 , C 18 , C 20 , C 21 , C 22 , C 24 , C 25 , C 26 , C 28 , C 29 , C 30 It may be an aryl group or an arylene group, and specifically, it may be phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, triphenylene, or a combination thereof, such as a combination of phenyl, naphthyl and phenanthrene.

[0118] In the case where at least one of the C ring and the D ring is an aromatic ring, the said aromatic ring is, for example, C6~C 60 , C6~C 30 , C6~C 29 , C6~C 28 , C6~C 27 , C6~C 26 , C6~C 25 , C6~C 24 , C6~C 23 , C6~C 22 , C6~C 21 , C6~C 20 , C6~C 19 , C6~C 18 , C6~C 17 , C6~C 16 , C6~C 15 , C6~C 14 , C6~C 13 , C6~C 10 , C6, C 10 , C 13 , C 14 , C 16 , C 17 , C 18 , C 20 , C 21 , C 22 , C 24 , C 25 , C 26 , C 28 , C 29, C 30 It may be an aromatic ring, specifically, phenyl, naphthyl, phenanthrene, triphenylene, etc.

[0119] Ar 1 , R 2 to R 5 , where at least one of the C ring and D ring is a heterocyclic ring, the heterocyclic ring is, for example, C2~C 60 , C2~C 30 , C2~C 25 , C2~C 20 , C2~C 16 , C2~C 12 , C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24 , C 25 , C 26 , C 27 , C 28 , C 29It may be a heterocyclic group such as pyridine, pyrimidine, pyrazine, triazine, indole, phenyl-indole, quinazolin, benzoquinazolin, quinoxaline, benzoquinoxaline, benzofuran, naphthobenzofuran, dibenzofuran, dynaphthofuran, phenantrobenzofuran, thiophene, benzothiophen, dibenzothiophen, naphthobenzothiophen, dynaphthiophen, phenantrobenzothiophen, carbazole, phenyl-carbazole, benzocarbazole, phenyl-benzocarbazole, naphthyl-benzocarbazole, dibenzocarbazole, indolocarbazole, benzothienopyrimidine, benzofuropyrimidine, benzothienopyrazine, benzofuropyrazine, dibenzocilol, It may be benzoxazole, naphthoxazole, phenanthrooxazole, dibenzothyenobenzoxazole, dibenzofurobenzoxazole, spyro[fluorene-9,9'-xanthen], etc.

[0120] R 2 to R 5 If at least one of them is an aliphatic ring, the aliphatic ring is, for example, C3~C 30 , C3~C 29 , C3~C 28 , C3~C 27 , C3~C 26 , C3~C 25 , C3~C 24 , C3~C 23 , C3~C 22 , C3~C 21 , C3~C 20 , C3~C 19 , C3~C 18 , C3~C 17 , C3~C 16 , C3~C 15 , C3~C 14 , C3~C 13 , C3~C 12 , C3~C 11 , C3~C 10 , C3~C8, C3~C6, C6, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C17 , C 18 It may be an aliphatic ring, and specifically, it may be cyclobutane, cyclopentane, cyclohexane, cyclohexene, bicycloheptane, adamantyl, etc.

[0121] R 2 to R 4 Where at least one of them is an alkyl group, the alkyl group is, for example, C1 to C 20 , C1~C 10 It can be an alkyl group such as C1~C4, C1, C2, C3, C4, etc., and, for example, a methyl group, ethyl group, propyl group, isopropyl group, butyl group, t-butyl group, pentyl group, etc., and the hydrogen of the alkyl group can be replaced with deuterium.

[0122] The above aryl group, arylene group, aromatic ring, heterocyclic group, aliphatic ring, fused ring, alkyl group, alkenyl group, alkyneyl group, alkoxy group, and aryloxy group are each deuterium; halogen; C1-C 20 alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; C1-C 20 alkoxy group of; C6-C 30 aryloxy group of; C1-C 20 alkyl group of; C2-C 20 alkene diary; C2-C 20 Alkin's Diary; C6-C 30 aryl group of; C6-C substituted with deuterium 30 aryl group of; C3-C 30 Aliphatic ring; C6-C 30 The aromatic ring and C3-C 30 A fused ring of an aliphatic ring; and a C2-C comprising at least one heteroatom among O, N, S, Si, and P. 30 It can be substituted with one or more substituents selected from the group consisting of heterocyclic rings, and the hydrogen of the substituent can be replaced with deuterium.

[0123] Preferably, at least one of the aryl group, arylene group, aromatic ring, heterocyclic group, aliphatic ring, fused ring, alkyl group, alkenyl group, alkyneyl group, alkoxy group, and aryloxy group is C1-C 20 alkyl group of; C6-C 30 aryl group of; C3-C 30 an aliphatic ring of; and a C2-C comprising at least one heteroatom among O, N, S, Si, and P. 30 It can be substituted with a substituent selected from the group of heterocyclic rings, and the hydrogens of these substituents can be replaced with deuterium.

[0124] The above Ar 1 and L 1 ...does not contain a fluorene group. Therefore, Ar 1 , L 1 This cannot be a fluorene group, and cases where they are substituted with a fluorene group are also excluded.

[0125] The above C ring may be selected from the group consisting of the following chemical formulas C-1 to ring C-15, but is not limited thereto.

[0126] <Chemical Formula C-1> <Chemical Formula C-2> <Chemical Formula C-3> <Chemical Formula C-4>

[0127]

[0128] <Chemical Formula C-5> <Chemical Formula C-6> <Chemical Formula C-7> <Chemical Formula C-8>

[0129]

[0130] <Chemical Formula C-9> <Chemical Formula C-10> <Chemical Formula C-11> <Chemical Formula C-12>

[0131]

[0132] <Chemical Formula C-13> <Chemical Formula C-14> <Chemical Formula C-15>

[0133]

[0134] In the above chemical formulas C-1 to C-15, v represents a site condensed to the X-containing 5-membered ring of chemical formula A, and R 4 is as defined in Chemical Formula 1, where d is an integer from 0 to 3, e is an integer from 0 to 5, and f is an integer from 0 to 7, and where these are integers greater than or equal to 2, multiple R 4 Each is either the same or different from the others.

[0135] The above D ring may be selected from the group consisting of the following chemical formulas D-1 to D-11, but is not limited thereto.

[0136] <Structural Formula D-1> <Structural Formula D-2> <Structural Formula D-3> <Structural Formula D-4>

[0137]

[0138] <Structural Formula D-5> <Structural Formula D-6> <Structural Formula D-7> <Structural Formula D-8>

[0139]

[0140] <Structural Formula D-9> <Structural Formula D-10> <Structural Formula D-11>

[0141]

[0142] In the above chemical formulas D-1 to D-11, v represents a site condensed to the X-containing 5-membered ring of chemical formula A, and W represents NR 6 , O or S.

[0143] R 4 is hydrogen; deuterium; C6~C 60 aryl group of; C2~C comprising at least one heteroatom among O, N, S, Si, and P 60 The heterocyclic group of; and C1~C 20 It is selected from the group consisting of alkyl groups.

[0144] R 6 Hydrogen; Deuterium; C6~C 30aryl group of; C2~C comprising at least one heteroatom among O, N, S, Si, and P 30 The heterocyclic group of; and C1~C 20 It is selected from the group consisting of alkyl groups.

[0145] d is an integer from 0 to 4, e is an integer from 0 to 6, f is an integer from 0 to 8, and g is an integer from 0 to 6, and if these are integers greater than or equal to 2, multiple R 4 Each is either the same or different from the others.

[0146] The above chemical formula B may be one of the following chemical formulas B-1 to B-4.

[0147] <Structural Formula B-1> <Structural Formula B-2> <Structural Formula B-3> <Structural Formula B-4>

[0148]

[0149] In the above chemical formulas B-1 to B-4, Y is O or S, and R 2 and R 3 Hydrogen; deuterium; C6~C independently 30 aryl group of; C2~C comprising at least one heteroatom among O, N, S, Si, and P 30 The heterocyclic group of; and C1~C 20 It is selected from the group consisting of alkyl groups, where b and c are as defined in Chemical Formula 1.

[0150] Specifically, the compound represented by the above chemical formula 1 may be one of the following compounds, but is not limited thereto.

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176] .

[0177] In another aspect, the present invention provides a material for an organic electrical device containing a compound of Formula 1 and a compound represented by Formula I below. Preferably, the material for an organic electrical device is a host material for a light-emitting layer. That is, a mixture of a compound represented by Formula 1 and a compound represented by Formula I can be used as a host for an organic layer.

[0178] The following chemical formula I is described in detail below.

[0179] <Chemical Formula I>

[0180]

[0181] In the above chemical formula I, each symbol can be defined as follows.

[0182] X A To X C is N or C(R'), and at least one of them is N. For example, X A To X C The ring containing may be pyridine, pyrimidine, or triazine.

[0183] Ar A or Ar C C6~C are independent of each other 60 aryl group; fluorenyl group; C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic ring of; C3~C 60 aliphatic ring; C3~C 60 The aliphatic ring and C6~C 60 The fused ring of the aromatic ring; and C1~C 30 It is selected from the group consisting of alkyl groups.

[0184] L A to L C are independent single bonds; C6~C 60 arylene group; fluorenyllene group; C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic ring of; C3~C 60 aliphatic ring of; and C3~C 60 The aliphatic ring and C6~C 60 It is selected from a group consisting of fused rings of aromatic rings.

[0185] The above R' is hydrogen; deuterium; halogen; cyano group; nitro group; C6~C 60aryl group; fluorenyl group; C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic ring of; C3~C 60 aliphatic ring; C6~C 60 The aromatic ring and C3~C 60 Fusion ring of the aliphatic ring; C1~C 20 alkyl group of; C2~C 20 The Alken Diary of; C2~C 20 Alkin's Diary; C1~C 20 alkoxy groups; and C6~C 60 It is selected from the group consisting of aryloxy groups.

[0186] The above Ar A or Ar C At least one of , R' is an aryl group, or L A to L C Where at least one of them is an arylene group, said arylene group or arylene group is, for example, C6~C 30 , C6~C 29 , C6~C 28 , C6~C 27 , C6~C 26 , C6~C 25 , C6~C 24 , C6~C 23 , C6~C 22 , C6~C 21 , C6~C 20 , C6~C 19 , C6~C 18 , C6~C 17 , C6~C 16 , C6~C 15 , C6~C 14 , C6~C 13 , C6~C 12 , C6~C 11 , C6~C 10 , C6, C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18It may be an aryl group or an arylene group, and specifically, it may be phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, triphenylene, etc.

[0187] The above Ar A or Ar C , R', L A to L C If at least one of them is a heterocyclic ring, the heterocyclic ring is, for example, C2~C 30 , C2~C 29 , C2~C 28 , C2~C 27 , C2~C 26 , C2~C 25 , C2~C 24 , C2~C 23 , C2~C 22 , C2~C 21 , C2~C 20 , C2~C 19 , C2~C 18 , C2~C 17 , C2~C 16 , C2~C 15 , C2~C 14 , C2~C 13 , C2~C 12 , C2~C 11 , C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24 , C 25 , C 26 , C 27 , C 28 , C29 It may be a heterocyclic group such as pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, indene, indole, phenyl-indole, benzodole, phenyl-benzodole, pyrazinoindole, quinoline, isoquinoline, benzoquinoline, pyridoquinoline, quinazoline, benzoquinazoline, dibenzoquinazoline, phenantroquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, benzofuran, naphthobenzofuran, dibenzofuran, dynaphthofuran, thiophene, benzothiophen, dibenzothiophen, naphthobenzothiophen, dynaphthiophen, carbazole, phenyl-carbazole, benzocarbazole, phenyl-benzocarbazole, It may be naphthyl-benzocarbazole, dibenzocarbazole, indolocarbazole, benzopuropyridine, benzothiopyridine, benzopuropyridine, benzothiopyrimidine, benzopuropyrimidine, benzothiopyrazine, benzopuropyrazine, benzimidazole, benzothiazole, benzoxazole, benzocilol, phenanthroline, dihydro-phenylphenazine, 10-phenyl-10H-phenoxazine, phenoxazine, phenothiazine, dibenzodioxin, benzodibenzodioxin, cyanthrene, 9,9-dimethyl-9H-xanthrene, 9,9-dimethyl-9H-thioxanthrene, dihydrodimethylphenylacridine, spiro[fluorene-9,9'-xanthrene], etc.

[0188] The above Ar A or Ar C At least one of , R' is a fluorene group, or L A to L C If at least one of them is a fluorenylene group, the fluorenyl group or fluorenylene group may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[b]fluorene-11,9'-fluorene], benzo[b]fluorene, 11,11-diphenyl-11H-benzo[b]fluorene, 9-(naphthalene-2-yl)9-phenyl-9H-fluorene, etc.

[0189] The above Ar A or Ar C , R', L A to LC If at least one of them is an aliphatic ring, the aliphatic ring is, for example, C3~C 30 , C3~C 29 , C3~C 28 , C3~C 27 , C3~C 26 , C3~C 25 , C3~C 24 , C3~C 23 , C3~C 22 , C3~C 21 , C3~C 20 , C3~C 19 , C3~C 18 , C3~C 17 , C3~C 16 , C3~C 15 , C3~C 14 , C3~C 13 , C3~C 12 , C3~C 11 , C3~C 10 , C3~C8, C3~C6, C6, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 It may be an aliphatic ring, specifically, a cyclohexane group, an adamantyl group, etc.

[0190] The above aryl group, arylene group, fluorenyl group, fluorenyllene group, heterocyclic group, aliphatic cycle, fused cycle, alkyl group, alkenyl group, alkyneyl group, alkoxy group, and aryloxy group are each deuterium; halogen; C1-C 20 alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; nitro group; C1-C 20 alkylthio group of; C1-C 20 alkoxy group of; C6-C 30aryloxy group of; C6-C 30 aryl thiologic; C1-C 20 alkyl group of; C2-C 20 alkene diary; C2-C 20 Alkin's Diary; C6-C 30 aryl group; fluoreneyl group; C3-C 30 Aliphatic ring; C6-C 30 The aromatic ring and C3-C 30 A fused ring of an aliphatic ring; and a C2-C comprising at least one heteroatom among O, N, S, Si, and P. 30 It can be substituted with one or more substituents selected from a group of heterocyclic rings, and adjacent substituents can bond with each other to form a ring, and the hydrogen of the substituent can be replaced with deuterium.

[0191] When at least one of the above aryl group, arylene group, fluorenyl group, fluorenyllene group, heterocyclic group, aliphatic cycle, fused cycle, alkyl group, alkenyl group, alkyneyl group, alkoxy group, aryloxy group, or a ring formed by the bonding of adjacent groups is substituted with an aryl group, the aryl group is, for example, C6 to C 30 , C6~C 29 , C6~C 28 , C6~C 27 , C6~C 26 , C6~C 25 , C6~C 24 , C6~C 23 , C6~C 22 , C6~C 21 , C6~C 20 , C6~C 19 , C6~C 18 , C6~C 17 , C6~C 16 , C6~C 15 , C6~C 14 , C6~C 13 , C6~C 12 , C6~C 11 , C6~C 10 , C6, C 10 , C 12 , C13 , C 14 , C 15 , C 16 , C 17 , C 18 It could be an aril of the back.

[0192] When at least one of the above aryl group, arylene group, fluorenyl group, fluorenyllene group, heterocyclic group, aliphatic group, fused group, alkyl group, alkenyl group, alkyneyl group, alkoxy group, aryloxy group, or a ring formed by the bonding of adjacent groups is substituted with a heterocyclic group, the heterocyclic group is, for example, C2~C 20 , C2~C 19 , C2~C 18 , C2~C 17 , C2~C 16 , C2~C 15 , C2~C 14 , C2~C 13 , C2~C 12 , C2~C 11 , C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 It can be a heterocyclic ring.

[0193] When at least one of the above aryl group, arylene group, fluorenyl group, fluorenyllene group, heterocyclic group, aliphatic group, fused group, alkyl group, alkenyl group, alkyneyl group, alkoxy group, aryloxy group, or a ring formed by the bonding of adjacent groups is substituted with an aliphatic group, the above aliphatic group is, for example, C3~C 30 , C3~C 29 , C3~C 28 , C3~C27 , C3~C 26 , C3~C 25 , C3~C 24 , C3~C 23 , C3~C 22 , C3~C 21 , C3~C 20 , C3~C 19 , C3~C 18 , C3~C 17 , C3~C 16 , C3~C 15 , C3~C 14 , C3~C 13 , C3~C 12 , C3~C 11 , C3~C 10 , C3~C8, C3~C6, C6, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 It could be a fatty ring on the back.

[0194] When at least one of the above aryl group, arylene group, fluorenyl group, fluorenyl group, heterocyclic group, aliphatic cyclic group, fused cyclic group, alkyl group, alkenyl group, alkyneyl group, alkoxy group, aryloxy group, or a ring formed by the bonding of adjacent groups is substituted with a fluorenyl group, the fluorenyl group may be, for example, 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[b]fluorene-11,9'-fluorene], benzo[b]fluorene, 11,11-diphenyl-11H-benzo[b]fluorene, 9-(naphthalene-2-yl)9-phenyl-9H-fluorene, etc.

[0195] The above Ar A or Ar C At least one of them may be selected from the group consisting of the following chemical formulas Ar-a to Ar-d, but is not limited thereto.

[0196] <Chemical Formula Ar-a> <Chemical Formula Ar-b>

[0197]

[0198] <Chemical Formula Ar-c> <Chemical Formula Ar-d>

[0199]

[0200] In the above chemical formulas Ar-a to Ar-d, each symbol is defined as follows.

[0201] Y A to Y C O, S, C(R) are independent of each other 21 )(R 22 ) or N(Ar 11 )am.

[0202] R A to R F , R 21 and R 22 are independently hydrogen; deuterium; halogen; C1-C 20 alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; nitro group; C1-C 20 alkylthio group of; C1-C 20 alkoxy group of; C6-C 30 aryloxy group of; C6-C 30 aryl thiologic; C1-C 20 alkyl group of; C2-C 20 alkene diary; C2-C 20 Alkin's Diary; C6-C 30 aryl group; fluorenyl group; C2-C comprising at least one heteroatom among O, N, S, Si, and P 30 heterocyclic; C3-C 30 aliphatic ring of; and C6-C 30 The aromatic ring and C3-C 30It is selected from a group consisting of fused rings of aliphatic rings, and neighboring groups can combine with each other to form rings, and R 21 and R 22 They can combine with each other to form a ring. Neighboring R 21 and R 22 When they combine with each other to form a ring, a spyro compound can be formed.

[0203] Neighboring R A R's or neighbors F When at least one pair of them combines to form a ring, the ring is C6~C 60 aryl ring; fluorene group; C3~C 60 an aliphatic ring of; C2~C comprising at least one heteroatom among O, N, S, Si, and P. 60 heterocyclic; and C3~C 60 The aliphatic ring and C6~C 60 It can be selected from a group consisting of fused rings of aromatic rings.

[0204] Ar 11 C1-C 20 alkyl group of; C6-C 30 aryl group; fluoreneyl group; C3-C 30 Aliphatic ring; C6-C 30 The aromatic ring and C3-C 30 A fused ring of an aliphatic ring; and a C2-C comprising at least one heteroatom among O, N, S, Si, and P. 30 It is selected from a group consisting of heterocycles.

[0205] ta and tc are integers from 0 to 3, tb and td are integers from 0 to 4, te is an integer from 0 to 5, and tf is an integer from 0 to 7; if these are integers greater than or equal to 2, then multiple R A Each or multiple R F Each is either the same or different from the others.

[0206] The above R A to R F , R21 and R 22 , Ar 11 deuterium; halogen; C1-C, respectively. 20 alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; nitro group; C1-C 20 alkylthio group of; C1-C 20 alkoxy group of; C6-C 30 aryloxy group of; C6-C 30 aryl thiologic; C1-C 20 alkyl group of; C2-C 20 alkene diary; C2-C 20 Alkin's Diary; C6-C 30 aryl group; fluorenyl group; C2-C comprising at least one heteroatom among O, N, S, Si, and P 30 heterocyclic; C3-C 30 aliphatic ring of; and C6-C 30 The aromatic ring and C3-C 30 It can be substituted with one or more substituents selected from the group consisting of fused rings of the aliphatic ring, and the hydrogen of the substituent can be replaced with deuterium.

[0207] The above formula Ar-a can be selected from the group consisting of the following formulas Ar-a-1 to Ar-a-4, the above formula Ar-b can be represented by the following formula Ar-b-1 or formula Ar-b-2, and the above formula Ar-d can be represented by the following formula Ar-d-1 or formula Ar-d-2.

[0208] <Chemical Formula Ar-a-1> <Chemical Formula Ar-a-2>

[0209]

[0210] <Chemical Formula Ar-a-3> <Chemical Formula Ar-a-4>

[0211]

[0212] <Chemical Formula Ar-b-1> <Chemical Formula Ar-b-2>

[0213]

[0214] <Chemical Formula Ar-d-1> <Chemical Formula Ar-d-2>

[0215]

[0216] In the above chemical formulas Ar-a-1 to Ar-a-4, Y A , R A , R B , ta, and tb are as defined in the chemical formula Ar-a, and in the above chemical formulas Ar-b-1 and Ar-b-2, Y B , Y C , R D , tc, and td are as defined in the chemical formula Ar-b, and in the above chemical formulas Ar-d-1 and Ar-d-2, R F , tf is equal to that defined in the chemical formula Ar-d.

[0217] L A to L C At least one of them is a single bond; and may be selected from the group consisting of the following chemical formulas b-1 to b-13, but is not limited thereto.

[0218] <Chemical Formula b-1> <Chemical Formula b-2> <Chemical Formula b-3>

[0219]

[0220] <Chemical Formula b-4> <Chemical Formula b-5> <Chemical Formula b-6>

[0221]

[0222] <Chemical Formula b-7> <Chemical Formula b-8> <Chemical Formula b-9> <Chemical Formula b-10>

[0223]

[0224] <Chemical Formula b-11> <Chemical Formula b-12> <Chemical Formula b-13>

[0225]

[0226] In the above chemical formulas b-1 to b-13, each symbol can be defined as follows.

[0227] Z 10 은 O, S, N(Ar 12 ) or C(R 23 )(R 24 )am.

[0228] Z 49 , Z 50 , Z 51 are independently N or C(R 25 ) and at least one of them is N.

[0229] R a1 to R a7 , R 23 to R 25 are independently hydrogen; deuterium; halogen; C1-C 20 alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; nitro group; C1-C 20 alkylthio group of; C1-C 20 alkoxy group of; C6-C 30 aryloxy group of; C6-C 30 aryl thiologic; C1-C 20 alkyl group of; C2-C 20 alkene diary; C2-C 20 Alkin's Diary; C6-C 30 aryl group; fluorenyl group; C2-C comprising at least one heteroatom among O, N, S, Si, and P 30 heterocyclic; C3-C 30 aliphatic ring of; and C6-C 30 The aromatic ring and C3-C 30It is selected from a group consisting of fused rings of aliphatic rings, and neighboring groups can combine with each other to form rings.

[0230] Neighboring R a1 R's or neighbors a7 When at least one pair of them combines to form a ring, the ring is C6~C 60 aryl ring; fluoreneyl group; C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic ring of; C3~C 60 aliphatic ring of; and C3~C 60 The aliphatic ring and C6~C 60 It can be selected from the group consisting of fused rings of aromatic rings, and neighboring R 23 and R 24 When they combine with each other to form a ring, a spyro compound can be formed.

[0231] Ar 12 is C1-C 20 alkyl group of; C6-C 30 aryl group; fluoreneyl group; C3-C 30 Aliphatic ring; C6-C 30 The aromatic ring and C3-C 30 A fused ring of an aliphatic ring; and a C2-C comprising at least one heteroatom among O, N, S, Si, and P. 30 It is selected from a group consisting of heterocycles.

[0232] a", c", d", and e" are each integers from 0 to 4, b" is an integer from 0 to 6, f" and g" are each integers from 0 to 3, h" is an integer from 0 to 2, and i" is an integer of 0 or 1; and if these are integers greater than or equal to 2, then multiple R a1 Each to R a7 Each is either the same or different from the others.

[0233] The above R a1 to R a7 , R 23 to R25 , Ar 12 are deuterium; halogen; and C1-C, respectively. 20 alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; nitro group; C1-C 20 alkylthio group of; C1-C 20 alkoxy group of; C6-C 30 aryloxy group of; C6-C 30 aryl thiologic; C1-C 20 alkyl group of; C2-C 20 alkene diary; C2-C 20 Alkin's Diary; C6-C 30 aryl group; fluorenyl group; C2~C comprising at least one heteroatom among O, N, S, Si and P 60 heterocyclic; C3-C 30 aliphatic ring of; and C6-C 30 The aromatic ring and C3-C 30 It can be substituted with one or more substituents selected from the group consisting of fused rings of the aliphatic ring, and the hydrogen of the substituent can be replaced with deuterium.

[0234] Specifically, the compound represented by the above chemical formula I may be one of the following compounds, but is not limited thereto.

[0235] The compound represented by the above chemical formula I may be one of the following compounds, but is not limited thereto.

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307] .

[0308] In another aspect, the present invention provides an electronic device comprising a display device including an organic electric element and a control unit for driving the display device, wherein the organic electric element includes a compound represented by Chemical Formula 1 or contains a compound represented by Chemical Formula 1 and Chemical Formula I. Preferably, these compounds are included in a light-emitting layer, and more preferably, are used as a host for the light-emitting layer.

[0309] In another aspect, the present invention provides a compound represented by Formula 1 obtained by depositing an organic layer in a manufacturing process of an organic electrical device, recovering the material of the organic layer from the deposition equipment, and purifying it. The purity of the compound obtained by recovery and purification is 99.9% or higher.

[0310] In another aspect, the present invention provides a method for recovering a compound comprising the steps of: depositing an organic layer material containing a compound represented by Formula 1; recovering the organic layer material attached to a deposition apparatus; and purifying the recovered organic layer material to obtain a compound represented by Formula 1 having a purity of 99.9% or higher.

[0311] The above purification step may include a step of recrystallizing the recovered organic layer material using a recrystallization solvent, a step of separating by adsorption using an adsorbent, and a step of purifying by sublimation.

[0312] The above recrystallization step may include a preliminary purification process using a recrystallization solvent to obtain a compound represented by Formula 1 with a purity of 98%.

[0313] Preferably, a polar solvent having a polarity index (PI) of 5.5 to 7.2 is used as the recrystallization solvent, or a mixture of a polar solvent having a polarity index of 5.5 to 7.2 and a non-polar solvent having a polarity index of 2.0 to 4.7 may be used.

[0314] When a mixture of a polar solvent and a non-polar solvent is used as a recrystallization solvent, the non-polar solvent may be used at a ratio of 15% (v / v) or less relative to the polar solvent.

[0315] Additionally, as a recrystallization solvent, preferably a single solvent of methylpyrrolidone (N-methylpyrrolidone: NMP); or a mixed polar solvent in which any one selected from the group consisting of dimethylimidazolidinone (1,3-dimethyl-2-imidazolidinone), 2-pyrrolidone, dimethylformamide (N,N-dimethyl formamide), dimethylacetamide, and dimethyl sulfoxide is mixed with the methylpyrrolidone; or a single or mixed nonpolar solvent selected from the group consisting of toluene, DCM (Dichloromethane), DCE (dichloroethane), THF (tetrahydrofuran), chloroform, ethyl acetate, and butanone; or a mixture of a polar solvent and a nonpolar solvent may be used.

[0316] The above preliminary purification process may include a step of dissolving an unpurified organic light-emitting material recovered from a deposition equipment in a polar solvent at 90°C to 120°C, and then cooling it to 0°C to 5°C to precipitate crystals.

[0317] The above preliminary purification process may include the step of dissolving an unpurified organic light-emitting material recovered from a deposition equipment in a polar solvent at 90°C to 120°C, then cooling it to 35°C to 40°C to add a non-polar solvent, and then cooling it to 0°C to 5°C to precipitate crystals.

[0318] The above preliminary purification process may include a step of dissolving an unpurified organic light-emitting material recovered from a deposition equipment in a non-polar solvent, concentrating the solvent, and precipitating crystals while removing the non-polar solvent.

[0319] The above preliminary purification process may include a step of first recrystallizing with a polar solvent and then recrystallizing again with a non-polar solvent.

[0320] In the adsorption separation step using the above adsorbent, activated carbon, silica gel, alumina, or known adsorption materials may be used as the adsorbent.

[0321] Hereinafter, examples of synthesis of Formula 1 and Formula I and examples of manufacturing of organic electric devices according to the present invention will be described in detail with reference to examples, but the present invention is not limited thereto.

[0322] [Synthetic Example]

[0323] Synthesis example of a compound of Chemical Formula 1

[0324] The compound (final product) represented by Chemical Formula 1 according to the present invention can be synthesized by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1 below, but is not limited thereto.

[0325] <Reaction Equation 1> (Hal is Cl, I, or Br)

[0326]

[0327] Example compounds of Sub 1

[0328] The compounds belonging to Sub 1 may be the following compounds, but are not limited thereto, and the FD-MS (Field Desorption-Mass Spectrometry) values ​​of the following compounds are as shown in Table 1.

[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] Compound FD-MS Compound FD-MS Sub1-1 m / z=245.12(C 18 H 15 N=245.32)Sub1-2m / z=385.15(C 28 H 19 NO=385.47)Sub1-3m / z=491.13(C 34 H 21 NOS=491.61)Sub1-4m / z=295.14(C 22 H 17 N=295.38)Sub1-5m / z=219.10(C 16 H 13 N=219.29)Sub1-6m / z=295.14(C 22 H17 N=295.38)Sub1-7m / z=351.11(C 24 H 17 NS=351.47)Sub1-8m / z=295.14(C 22 H 17 N=295.38)Sub1-9m / z=441.12(C 30 H 19 NOS=441.55)Sub1-10m / z=385.15(C 28 H 19 NO=385.47)Sub1-11m / z=435.16(C 32 H 21 NO=435.53)Sub1-12m / z=335.13(C 24 H 17 NO=335.41)Sub1-13m / z=300.17(C 22 H 12 D5N=300.42)Sub1-14m / z=335.13(C 24 H 17 NO=335.41)Sub1-15m / z=395.17(C 30 H 21 N=395.50)Sub1-16m / z=401.12(C 28 H 19 NS=401.53)Sub1-17m / z=441.12(C 30 H 19 NOS=441.55)Sub1-18m / z=531.13(C 36 H 21 NO2S=531.63)Sub1-19m / z=425.14(C 30 H 19 NO2=425.49)Sub1-20m / z=451.14(C 32 H 21 NS=451.59)Sub1-21m / z=485.18(C 36 H 23 NO=485.59)Sub1-22m / z=395.17(C 30 H 21 N=395.50)Sub1-23m / z=385.15(C 28 H 19 NO=385.47)Sub1-24m / z=385.15(C28 H 19 NO=385.47)Sub1-25m / z=300.17(C 22 H 12 D5N=300.42)Sub1-26m / z=385.15(C 28 H 19 NO=385.47)Sub1-27m / z=385.15(C 28 H 19 NO=385.47)Sub1-28m / z=385.15(C 28 H 19 NO=385.47)Sub1-29m / z=435.16(C 32 H 21 NO=435.53)Sub1-30m / z=425.14(C 30 H 19 NO2=425.49)Sub1-31m / z=441.12(C 30 H 19 NOS=441.55)Sub1-32m / z=491.13(C 34 H 21 NOS=491.61)Sub1-33m / z=435.16(C 32 H 21 NO=435.53)Sub1-34m / z=385.15(C 28 H 19 NO=385.47)Sub1-35m / z=547.11(C 36 H 21 NOS2=547.69)Sub1-36m / z=557.13(C 38 H 23 NS2=557.73)Sub1-37m / z=401.12(C 28 H 19 NS=401.53)Sub1-38m / z=385.15(C 28 H 19 NO=385.47)Sub1-39m / z=401.12(C 28 H 19 NS=401.53)Sub1-40m / z=401.12(C 28 H 19 NS=401.53)Sub1-41m / z=507.11(C 34 H 21NS2=507.67)Sub1-42m / z=435.16(C 32 H 21 NO=435.53)Sub1-43m / z=547.11(C 36 H 21 NOS2=547.69)Sub1-44m / z=435.16(C 32 H 21 NO=435.53)Sub1-45m / z=385.15(C 28 H 19 NO=385.47)Sub1-46m / z=395.17(C 30 H 21 N=395.50)Sub1-47m / z=475.16(C 34 H 21 NO2=475.55)Sub1-48m / z=375.11(C 26 H 17 NS=375.49)Sub1-49m / z=385.15(C 28 H 19 NO=385.47)Sub1-50m / z=345.15(C 26 H 19 N=345.44)Sub1-51m / z=335.13(C 24 H 17 NO=335.41)Sub1-52m / z=245.12(C 18 H 15 N=245.32)Sub1-53m / z=321.15(C 24 H 19 N=321.42)Sub1-54m / z=302.18(C 22 H 10 D7N=302.43)Sub1-55m / z=335.13(C 24 H 17 NO=335.41)Sub1-56m / z=300.17(C 22 H 12 D5N=300.42)Sub1-57m / z=351.11(C 24 H 17 NS=351.47)Sub1-58m / z=269.12(C 20 H 15 N=269.35)Sub1-59m / z=371.17(C 28 H21 N=371.48)Sub1-60m / z=351.20(C 26 H 25 N=351.49)Sub1-61m / z=345.15(C 26 H 19 N=345.44)Sub1-62m / z=295.14(C 22 H 17 N=295.38)Sub1-63m / z=335.13(C 24 H 17 NO=335.41)Sub1-64m / z=301.17(C 22 H 11 D6N=301.42)Sub1-65m / z=401.12(C 28 H 19 NS=401.53)Sub1-66m / z=345.15(C 26 H 19 N=345.44)Sub1-67m / z=394.20(C 28 H 10 D9NO=394.52)Sub1-68m / z=335.13(C 24 H 17 NO=335.41)Sub1-69m / z=250.15(C 18 H 10 D5N=250.36)Sub1-70m / z=401.12(C 28 H 19 NS=401.53)Sub1-71m / z=295.14(C 22 H 17 N=295.38)Sub1-72m / z=441.12(C 30 H 19 NOS=441.55)Sub1-73m / z=351.20(C 26 H 25 N=351.49)Sub1-74m / z=351.20(C 26 H 25 N=351.49)Sub1-75m / z=335.13 (C 24 H 17 NO=335.41)Sub1-76m / z=335.13(C 24 H 17 NO=335.41)Sub1-77m / z=542.27 (C40 H 34 N2=542.73)Sub1-78m / z=415.21(C 30 H 17 D5N2=415.55)Sub1-79m / z=500.19 (C 36 H 24 N2O=500.60)Sub1-80m / z=466.24(C 34 H 30 N2=466.63)Sub1-81m / z=410.18 (C 30 H 22 N2=410.52)Sub1-82m / z=516.17(C 36 H 24 N2S=516.66)Sub1-83m / z= 510.21(C 38 H 26 N2=510.64)Sub1-84m / z=460.19(C 34 H 24 N2=460.58)Sub1-85m / z=395.17 (C 30 H 21 N=395.51)Sub1-86m / z=503.17(C 36 H 25 NS=503.66)Sub1-87m / z=497.21(C 38 H 27 N=497.64)Sub1-88m / z=371.17(C 28 H 21 N=371.48)Sub1-89m / z=419.23(C 30 H 13 D9N2=419.57)Sub1-90m / z=503.17(C 36 H 25 NS=503.66)Sub1-91m / z=460.19(C 34 H 24 N2=460.58)Sub1-92m / z=410.18(C 30 H 22 N2=410.52)Sub1-93m / z=410.18(C 30 H 22 N2=410.52)Sub1-94m / z=516.17(C 36 H 24N2S=516.66)Sub1-95m / z=592.29(C 44 H 36 N2=592.79)Sub1-96m / z=460.19(C 34 H 24 N2=460.58)Sub1-97m / z=460.19(C 34 H 24 N2=460.58)Sub1-98m / z=527.17(C 38 H 25 NS=527.68)Sub1-99m / z=537.21(C 40 H 27 NO=537.66)Sub1-100m / z=371.48(C 27 H 23 N=371.48)

[0355] Example compounds of Sub 2

[0356] The compounds belonging to Sub 2 may be the following compounds, but are not limited thereto, and the FD-MS (Field Desorption-Mass Spectrometry) values ​​of the following compounds are as shown in Table 2.

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369] 화합물FD-MS화합물FD-MSSub2-1m / z=344.04(C 22 H 13 ClS=344.86)Sub2-2m / z=350.08(C 22 H7D6ClS=350.89)Sub2-3m / z=351.09(C 22 H6D7ClS=351.90)Sub2-4m / z=328.07(C 22 H 13 ClO=328.79)Sub2-5m / z=344.04(C 22 H 13 ClS=344.86)Sub2-6m / z=328.07(C 22 H 13 ClO=328.79)Sub2-7m / z=378.08(C 26 H 15 C lO =378.86)Sub2-8m / z=344.04(C 22 H 13 ClS=344.86)Sub2-9m / z=328.07(C 22 H 13 ClO=328.79)Sub2-10m / z=344.04(C 22 H 13 ClS=344.86)Sub2-11m / z=328.07(C 22 H 13 ClO=328.79)Sub2-12m / z=350.08(C 22 H7D6ClS=350.89)Sub2-13m / z=334.10(C 22 H7D6ClO=334.83)Sub2-14m / z=335.11(C 22 H6D7ClO=335.84)Sub2-15m / z=404.10(C 28 H 17 ClO=404.89)Sub2-16m / z=470.09(C 32 H 19 ClS=471.01)Sub2-17m / z=510.08(C 34 H 19 ClOS=511.03)Sub2-18m / z=510.08(C 34 H19 ClOS=511.03)Sub2-19m / z=454.11(C 32 H 19 ClO=454.95)Sub2-20m / z=420.07(C 28 H 17 ClS=420.95)Sub2-21m / z=510.08(C 34 H 19 ClOS=511.03)Sub2-22m / z=384.13(C 26 H 21 ClO=384.90)Sub2-23m / z=404.10(C 28 H 17 ClO=404.89)Sub2-24m / z=420.07(C 28 H 17 ClS=420.95)Sub2-25m / z=510.08(C 34 H 19 ClOS=511.03)Sub2-26m / z=454.11(C 32 H 19 ClO=454.95)Sub2-27m / z=510.08(C 34 H 19 ClOS=511.03)Sub2-28m / z=460.16(C 32 H 25 ClO=461.00)Sub2-29m / z=342.08(C 23 H 15 ClO=342.82)Sub2-30m / z=510.08(C 34 H 19 ClOS=511.03)Sub2-31m / z=510.08(C 34 H 19 ClOS=511.03)Sub2-32m / z=404.10(C 28 H 17 ClO=404.89)Sub2-33m / z=420.07(C 28 H 17 ClS=420.95)Sub2-34m / z=510.08(C 34 H 19 ClOS=511.03)Sub2-35m / z=526.06(C 34 H 19ClS2=527.10)Sub2-36m / z=420.07(C 28 H 17 ClS=420.95)Sub2-37m / z=404.10(C 28 H 17 ClO=404.89)Sub2-38m / z=526.06(C 34 H 19 ClS2=527.10)Sub2-39m / z=404.10(C 28 H 17 ClO=404.89)Sub2-40m / z=334.10(C 22 H7D6ClO=334.83)Sub2-41m / z=426.12(C 28 H 23 ClS=427.00)Sub2-42m / z=454.11(C 32 H 19 ClO=454.95)Sub2-43m / z=404.10(C 28 H 17 ClO=404.89)Sub2-44m / z=425.11(C 28 H 12 D5ClS=425.98)Sub2-45m / z=348.07(C 22 H9D4ClS=348.88)

[0370] Synthesis example of the final compound

[0371] Synthesis example of P-1

[0372]

[0373] (1) Synthetic example of Sub2-1

[0374] Sub2-1-a (23.29 g, 72.58 mmol), Sub2-1-b (20 g, 87.69 mmol), Pd(PPh3)4 (3.04 g, 2.63 mmol), K2CO3 (24.24 g, 175.38 mmol), THF (225 mL), and H2O (75 mL) were added to a round-bottom flask and stirred at 60 °C for 8 hours. After the reaction was complete, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried with MgSO4 and concentrated. Subsequently, the concentrate was purified using a silica gel column and recrystallized to obtain 24.8 g of product (yield: 84.5%).

[0375] (2) Synthesis example of P-1

[0376] Sub1-1 (14.23 g, 57.99 mmol), Sub2-1 (20 g, 57.99 mmol), Pd2(dba)3 (1.59 g, 1.74 mmol), NaOt-Bu (8.84 g, 115.98 mmol), P(t-Bu)3 (1.5 mL, 3.48 mmol), and Toluene (270 mL) were added to a round-bottom flask and stirred at 120 °C for 6 hours. Upon completion of the reaction, the reaction product was filtered to obtain a solid product, which was then dissolved in Toluene and filtered through a silica gel filter while heated. Subsequently, the filtrate was concentrated, purified using a silica gel column, and recrystallized to obtain 40.21 g of product (yield: 89%).

[0377] Synthesis example of P-12

[0378]

[0379] (1) Synthetic example of Sub2-4

[0380] Sub2-1-a (19.32 g, 91.09 mmol), Sub2-4-b (20 g, 82.81 mmol), Pd(PPh3)4 (2.87 g, 2.48 mmol), K2CO3 (22.89 g, 165.62 mmol), THF (200 mL), and H2O (70 mL) were added to a round-bottom flask and stirred at 60 °C for 3 hours, after which the same process as the synthesis example of Sub2-1 was performed to obtain 23.8 g of product (yield: 87.4%).

[0381] (2) Synthesis example of P-12

[0382] Sub1-12 (20.0 g, 59.63 mmol), Sub2-4 (21.57 g, 65.59 mmol), Pd2(dba)3 (1.64 g, 1.79 mmol), NaOt-Bu (11.46 g, 119.26 mmol), P(t-Bu)3 (1.45 mL, 3.58 mmol), and Toluene (200 mL) were added to a round-bottom flask and stirred at 120 °C for 3 hours. Then, the same process as in the synthesis example of P-1 above was performed to obtain 30.43 g of product (yield: 81.3%).

[0383] Synthesis example of P-17

[0384]

[0385] (1) Synthetic example of Sub2-5

[0386] Sub2-1-a (30.0 g, 124.2 mmol), Sub2-5-b (31.16 g, 136.6 mmol), Pd(PPh3)4 (4.31 g, 3.772 mmol), K2CO3 (34.34 g, 248.4 mmol), THF (310 mL), and H2O (100 mL) were added to a round-bottom flask and stirred at 50 °C for 8 hours, after which the same process as the synthesis example of Sub2-1 was performed to obtain 34.5 g of product (yield: 80.73%).

[0387] (2) Synthetic example of Sub1-17

[0388] Sub1-17-a (45.5 g, 118.1 mmol), Sub1-17-b (10.0 g, 107.4 mmol), Pd2(dba)3 (2.95 g, 3.221 mmol), NaOt-Bu (20.64 g, 214.8 mmol), P(t-Bu)3 (2.6 mL, 6.44 mmol), and Toluene (350 mL) were added to a round-bottom flask and stirred at 120 °C for 6 hours, after which the same process as the synthesis example of P-1 above was performed to obtain 30.8 g of product (yield: 64.96%).

[0389] (3) Synthesis example of P-17

[0390] Sub1-17 (30 g, 67.94 mmol), Sub2-5 (25.7 g, 74.74 mmol), Pd2(dba)3 (1.87 g, 4.08 mmol), NaOt-Bu (13.06 g, 135.9 mmol), P(t-Bu)3 (1.7 mL, 4.08 mmol), and Toluene (230 mL) were added to a round-bottom flask and stirred at 120 °C for 12 hours, after which the same process as the synthesis example of P-1 above was performed to obtain 42.5 g of product (yield: 83.41%).

[0391] Synthesis example of P-24

[0392]

[0393] (1) Synthetic example of Sub2-7

[0394] Sub2-1-a (20.0 g, 82.81 mmol), Sub2-7-b (23.87 g, 91.09 mmol), Pd(PPh3)4 (2.87 g, 2.48 mmol), K2CO3 (22.89 g, 165.62 mmol), THF (200 mL), and H2O (70 mL) were added to a round-bottom flask and stirred at 40 ℃ for 6 hours, after which the same process as the synthesis example of Sub2-1 was performed to obtain 20.8 g of product (yield: 66.3%).

[0395] (2) Synthesis example of P-24

[0396] Sub1-24 (19.0 g, 49.30 mmol), Sub2-7 (20.5 g, 54.22 mmol), Pd2(dba)3 (1.35 g, 1.48 mmol), NaOt-Bu (9.47 g, 98.58 mmol), P(t-Bu)3 (1.2 mL, 2.96 mmol), and Toluene (160 mL) were added to a round-bottom flask and stirred at 120 °C for 19 hours, after which the same process as the synthesis example of P-1 above was performed to obtain 27.6 g of product (yield: 76.93%).

[0397] Synthesis example of P-28

[0398]

[0399] Sub1-28 (25.0 g, 64.86 mmol), Sub29 (23.46 g, 71.34 mmol), Pd2(dba)3 (1.78 g, 1.94 mmol), NaOt-Bu (12.47 g, 129.72 mmol), P(t-Bu)3 (1.6 mL, 3.89 mmol), and Toluene (220 mL) were added to a round-bottom flask and stirred at 120 °C for 20 hours. Then, the same process as in the synthesis example of P-1 was performed to obtain 40.54 g of product (yield: 92.22%).

[0400] Synthesis example of P-40

[0401]

[0402] Sub1-40 (25.0 g, 62.26 mmol), Sub2-10 (23.62 g, 68.49 mmol), Pd2(dba)3 (1.71 g, 1.87 mmol), NaOt-Bu (11.97 g, 124.5 mmol), P(t-Bu)3 (1.5 mL, 3.74 mmol), and Toluene (200 mL) were added to a round-bottom flask and stirred at 120 °C for 15 hours, after which the same process as the synthesis example of P-1 above was performed to obtain product 38.76 (yield: 87.7%).

[0403] Synthesis example of P-47

[0404]

[0405] (1) Synthetic example of Sub1-47

[0406] Sub1-47-a (25 g, 107.2 mmol), Sub1-47-b (32.86 g, 117.9 mmol), Pd2(dba)3 (2.94 g, 3.22 mmol), NaOt-Bu (20.6 g, 214.3 mmol), P(t-Bu)3 (2.6 mL, 6.43 mmol), and Toluene (350 mL) were added to a round-bottom flask and stirred at 120 °C for 6 hours, after which the same process as the synthesis example of P-1 above was performed to obtain 42.3 g of product (yield: 83.0%).

[0407] (2) Synthesis example of P-47

[0408] Sub1-47 (20 g, 42.06 mmol), Sub2-10 (15.96 g, 46.26 mmol), Pd2(dba)3 (1.16 g, 1.26 mmol), NaOt-Bu (8.08 g, 84.11 mmol), P(t-Bu)3 (1.0 mL, 2.53 mmol), and Toluene (140 mL) were added to a round-bottom flask and stirred at 120 °C for 15 hours, after which the same process as the synthesis example of P-1 above was performed to obtain 28.21 g of product (yield: 85.6%).

[0409] Synthesis example of P-58

[0410]

[0411] (1) Synthetic example of Sub2-23

[0412] Sub2-1-a (25.0 g, 103.5 mmol), Sub2-23-b (32.8 g, 113.9 mmol), Pd(PPh3)4 (3.59 g, 3.105 mmol), K2CO3 (28.61 g, 207.0 mmol), THF (260 mL), and H2O (85 mL) were added to a round-bottom flask and stirred at 50 °C for 8 hours, after which the same process as the synthesis example of Sub2-1 was performed to obtain 36.96 g of product (yield: 88.2%).

[0413] (2) Synthesis example of P-58

[0414] Sub1-58 (20.0 g, 74.25 mmol), Sub2-23 (33.07 g, 81.68 mmol), Pd2(dba)3 (2.04 g, 2.278 mmol), NaOt-Bu (14.27 g, 148.5 mmol), P(t-Bu)3 (1.8 mL, 4.455 mmol), and Toluene (250 mL) were added to a round-bottom flask and stirred at 120 °C for 6 hours. Then, the same process as in the synthesis example of P-1 was performed to obtain 42.3 g of product (yield: 91.2%).

[0415] Synthesis example of P-69

[0416]

[0417] (1) Synthetic example of Sub2-31

[0418] Sub2-1-a (25 g, 103.5 mmol), Sub2-31-b (44.89 g, 113.9 mmol), Pd(PPh3)4 (3.59 g, 3.105 mmol), K2CO3 (28.61 g, 207.0 mmol), THF (260 mL), and H2O (85 mL) were added to a round-bottom flask and stirred at 40 ℃ for 3 hours, after which the same process as the synthesis example of Sub2-1 was performed to obtain 38.75 g of product (yield: 73.25%).

[0419] (2) Synthesis example of P-69

[0420] Sub1-69 (34.4 g, 67.26 mmol), Sub2-31 (15 g, 61.15 mmol), Pd2(dba)3 (1.68 g, 3.669 mmol), NaOt-Bu (11.75 g, 122.3 mmol), P(t-Bu)3 (1.5 mL, 3.66 mmol), and Toluene (200 mL) were added to a round-bottom flask and stirred at 120 °C for 6 hours, after which the same process as the synthesis example of P-1 above was performed to obtain 39.38 g of product (yield: 89.46%).

[0421] P-83 Synthetic Example

[0422]

[0423] (1) Synthetic example of Sub1-83

[0424] Sub1-83-a (25 g, 96.78 mmol), Sub1-83-b (30.74 g, 106.5 mmol), Pd2(dba)3 (2.66 g, 2.90 mmol), NaOt-Bu (18.60 g, 193.5 mmol), P(t-Bu)3 (2.4 mL, 5.807 mmol), and Toluene (320 mL) were added to a round-bottom flask and stirred at 120 °C for 6 hours, after which the same process as the synthesis example of P-1 above was performed to obtain 42.30 g of product (yield: 85.6%).

[0425] (2) Synthesis example of P-83

[0426] Sub1-83 (30 g, 58.75 mmol), Sub2-6 (21.25 g, 64.62 mmol), Pd2(dba)3 (1.62 g, 1.76 mmol), NaOt-Bu (11.30 g, 117.5 mmol), P(t-Bu)3 (1.4 mL, 3.525 mmol), and Toluene (200 mL) were added to a round-bottom flask and stirred at 120 °C for 16 hours. Then, the same process as in the synthesis example of P-1 was performed to obtain 38.90 g of product (yield: 82.46%).

[0427] The FD-MS values ​​of compounds P-1 to P-100 of the present invention prepared according to the synthesis examples above are as shown in Table 3 below.

[0428] Compound FD-MS Compound FD-MSP-1 m / z=553.19(C 40 H 27 NS=553.72)P-2m / z=699.25(C 50 H 25 D6NOS=699.90)P-3m / z=799.20(C 56 H 33 NOS2=800.01)P-4m / z= 610.25(C 44 H 22 D7NS=610.83)P-5m / z=527.17(C 38 H 25 NS=527.68)P-6m / z=603.20(C 44 H 29 NS=603.78)P-7m / z=643.20(C 46 H 29 NOS=643.80)P-8m / z=587.22(C 44 H 29 NO=587.72)P-9m / z=749.18(C 52 H 31 NOS2=749.95)P-10m / z=693.21(C 50 H 31 NOS=693.86)P-11m / z=727.25(C 54 H 33 NO2=727.86)P-12m / z=627.22(C 46 H 29 NO2=627.74)P-13m / z=608.23(C 44 H 24 D5NS=608.81)P-14m / z=643.20(C 46 H 29 NOS=643.80)P-15m / z=687.26(C 52 H 31 NO=687.84)P-16m / z=693.21(C 50 H 31 NOS=693.86)P-17m / z=749.18(C 52 H31 NOS2=749.95)P-18m / z=839.20(C 58 H 33 NO2S2=840.03)P-19m / z=733.21(C 52 H 31 NO2S=733.88)P-20m / z=759.21(C 54 H 33 NS2=759.98)P-21m / z=793.24(C 58 H 35 NOS=793.98)P-22m / z=703.23(C 52 H 33 NS=703.90)P-23m / z=693.21(C 50 H 31 NOS=693.86)P-24m / z=753.27(C 56 H 35 NO2=753.90)P-25m / z=608.23(C 44 H 24 D5NS=608.81)P-26m / z=693.21(C 50 H 31 NOS=693.86)P-27m / z=693.21(C 50 H 31 NOS=693.86)P-28m / z=677.24(C 50 H 31 NO2=677.80)P-29m / z=743.23(C 54 H 33 NOS=743.92)P-30m / z=717.23(C 52 H 31 NO3=717.82)P-31m / z=733.21(C 52 H 31 NO2S=733.88)P-32m / z=799.20(C 56 H 33 NOS2=800.01)P-33m / z=743.23(C 54 H 33 NOS=743.92)P-34m / z=677.24(C 50 H 31 NO2=677.80)P-35m / z=855.17(C 58 H 33NOS3=856.09)P-36m / z=865.19(C 60 H 35 NS3=866.13)P-37m / z=709.19(C 50 H 31 NS2=709.92)P-38m / z=677.24(C 50 H 31 NO2=677.80)P-39m / z=715.23(C 50 H 25 D6NS2=715.96)P-40m / z=709.19(C 50 H 31 NS2=709.92)P-41m / z=815.18(C 56 H 33 NS3=816.07)P-42m / z=743.23(C 54 H 33 NOS=743.92)P-43m / z=855.17(C 58 H 33 NOS3=856.09)P-44m / z=743.23(C 54 H 33 NOS=743.92)P-45m / z=677.24(C 50 H 31 NO2=677.80)P-46m / z=687.26(C 52 H 33 NO=687.84)P-47m / z=783.22(C 56 H 33 NO2S=783.94)P-48m / z= 673.23(C 48 H 23 D6NOS=673.86)P-49m / z=684.28(C 50 H 24 D7NO2=684.28)P-50m / z=713.27(C 54 H 35 NO=713.88)P-51m / z=769.24(C 56 H 35 NOS=769.96)P-52m / z=719.23(C 52 H 33 NOS=719.90)P-53m / z=613.24(C 46 H 31NO=613.76)P-54m / z=720.32(C 54 H 28 D7NO=720.92)P-55m / z=719.23(C 52 H 33 NOS=719.90)P-56m / z=774.28(C 56 H 30 D5NOS=774.99)P-57m / z=699.26(C 50 H 37 NOS=699.91)P-58m / z=637.24(C 48 H 31 NO=637.78)P-59m / z=755.26(C 56 H 37 NS=755.98)P-60m / z=825.31(C 60 H 43 NOS=826.07)P-61m / z=713.27(C 54 H 35 NO=713.88)P-62m / z=713.27(C 54 H 35 NO=713.88)P-63m / z=719.23(C 52 H 33 NOS=719.90)P-64m / z=775.28(C 56 H 29 D6NOS=776.00)P-65m / z=825.31(C 60 H 43 NOS=826.07)P-66m / z=651.26 (C 49 H 33 NO=651.81)P-67m / z=778.30(C 56 H 26 D9NOS=779.02)P-68m / z=809.24(C 58 H 35 NO2S=809.98)P-69m / z=728.28(C 52 H 24 D9NOS=728.96)P-70m / z=769.24(C 56 H 35 NOS=769.96)P-71m / z=679.23(C 50 H 33NS=679.88)P-72m / z=915.23(C 64 H 37 NO2S2=916.12)P-73m / z=841.28(C 60 H 43 NS2=842.13)P-74m / z=735.30(C 54 H 41 NS=735.99)P-75m / z=703.25(C 52 H 33 NO2=703.84)P-76m / z=825.22(C 58 H 35 NOS2=826.04)P-77m / z=850.34(C 62 H 46 N2S=851.12)P-78m / z=723.28(C 52 H 29 D5N2S=723.95)P-79m / z=868.31(C 64 H 40 N2O2=869.04)P-80m / z=774.31(C 56 H 42 N2S=775.03)P-81m / z=702.27(C 52 H 34 N2O=702.86)P-82m / z=830.27(C 58 H 30 D6N2S2=831.10)P-83m / z=802.30(C 60 H 38 N2O=802.98)P-84m / z=768.26(C 56 H 36 N2S=768.98)P-85m / z=687.26(C 52 H 33 NO=687.84)P-86m / z=811.24(C 58 H 37 NS2=812.06)P-87m / z=789.30(C 60 H 39 NO=789.98)P-88m / z=679.23(C 50 H 33 NS=679.88)P-89m / z=800.32(C 58 H 44N2S=801.06)P-90m / z=921.31(C 68 H 43 NOS=922.16)P-91m / z=828.31(C 62 H 40 N2O=829.01)P-92m / z=799.31(C 58 H 33 D5N2S=800.05)P-93m / z=711.32(C 52 H 25 D9N2O=711.91)P-94m / z=824.23(C 58 H 36 N2S2=825.06)P-95m / z=884.38(C 66 H 48 N2O=885.12)P-96m / z=772.29(C 56 H 32 D4N2S=773.00)P-97m / z=768.26(C 56 H 36 N2S=768.98)P-98m / z=819.26(C 60 H 37 NOS=820.02)P-99m / z=829.30(C 62 H 39 NO2=830.00)P-100m / z=653.27(C 49 H 35 NO=653.82)

[0429] Synthesis example of Chemical Formula I

[0430] The compound represented by Chemical Formula I can be prepared by referring to a known synthesis method (named reaction) or published patent publications, for example, Korean Patent Publication No. 2020-0129334, No. 2022-0055392, No. 2023-000502, but is not limited thereto.

[0431] The FD-MS values ​​of compounds N-1 to N-284 represented by chemical formula I are as shown in Table 4 below.

[0432] Compound FD-MS Compound FD-MSN-1 m / z=399.14(C 27 H 17N3O=399.45)N-2m / z=415.11(C 27 H 17 N3S=415.51)N-3m / z=474.18(C 33 H 22 N4=474.57)N-4m / z=449.15(C 31 H 19 N3O=449.51)N-5m / z=449.15(C 31 H 19 N3O=449.51)N-6m / z=515.15(C 35 H 21 N3S=515.63)N-7m / z=600.23(C 43 H 28 N4=600.73)N-8m / z=499.17(C 35 H 21 N3O=499.57)N-9m / z=551.20(C 39 H 25 N3O=551.65)N-10m / z=567.18(C 39 H 25 N3S=567.71)N-11m / z=702.28(C 51 H 34 N4=702.86)N-12m / z=657.22(C 46 H 31 N3S=657.84)N-13m / z=551.20(C 39 H 25 N3O=551.65)N-14m / z=541.16(C 37 H 23 N3S=541.67)N-15m / z=700.26(C 51 H 32 N4=700.85)N-16m / z=703.21(C 50 H 29 N3S=703.86)N-17m / z=525.18(C 37 H 23 N3O=525.61)N-18m / z=591.18(C 41 H 25 N3S=591.73)N-19m / z=627.24(C 44 H 29 N5=627.75)N-20m / z=524.20(C 37 H24 N4=524.63)N-21m / z=551.20(C 39 H 25 N3O=551.65)N-22m / z=567.18(C 39 H 25 N3S=567.71)N-23m / z=702.28(C 51 H 34 N4=702.86)N-24m / z=474.18(C 33 H 22 N4=474.57)N-25m / z=779.29(C 57 H 37 N3O=779.94)N-26m / z=731.24(C 52 H 33 N3S=731.92)N-27m / z=601.23(C 42 H 27 N5=601.71)N-28m / z=475.17(C 33 H 21 N3O=475.55)N-29m / z=641.21(C 45 H 27 N3O2=641.73)N-30m / z=746.21(C 51 H 30 N4OS=746.89)N-31m / z=716.26(C 51 H 32 N4O=716.84)N-32m / z=681.19(C 47 H 27 N3OS=681.81)N-33m / z=475.17(C 33 H 21 N3O=475.55)N-34m / z=491.15(C 33 H 21 N3S=491.61)N-35m / z=550.22(C 39 H 26 N4=550.67)N-36m / z=525.18(C 37 H 23 N3O=525.61)N-37m / z=475.17(C 33 H 21 N3O=475.55)N-38m / z=491.15(C 33 H 21N3S=491.61)N-39m / z=704.27(C 49 H 32 N6=704.84)N-40m / z=541.16(C 37 H 23 N3S=541.67)N-41m / z=551.20(C 39 H 25 N3O=551.65)N-42m / z=541.16(C 37 H 23 N3S=541.67)N-43m / z=626.25(C 45 H 30 N4=626.76)N-44m / z=676.26(C 49 H 32 N4=676.82)N-45m / z=551.2(C 39 H 25 N3O=551.65)N-46m / z=567.18(C 39 H 25 N3S=567.71)N-47m / z=614.25(C 44 H 30 N4=614.75)N-48m / z=575.17(C 39 H 21 N5O=575.63)N-49m / z=525.18(C 37 H 23 N3O=525.61)N-50m / z=541.16(C 37 H 23 N3S=541.67)N-51m / z=600.23(C 43 H 28 N4=600.73)N-52m / z=625.22(C 45 H 27 N3O=625.73)N-53m / z=525.18(C 37 H 23 N3O=525.61)N-54m / z=591.18(C 41 H 25 N3S=591.73)N-55m / z=600.23(C 43 H 28 N4=600.73)N-56m / z=693.22(C 49 H 31 N3S=693.87)N-57m / z=505.12(C33 H 19 N3OS=505.60)N-58m / z=641.21(C 45 H 27 N3O2=641.73)N-59m / z=571.12(C 37 H 21 N3S2=571.72)N-60m / z=564.20(C 39 H 24 N4O=564.65)N-61m / z=581.16(C 39 H 23 N3OS=581.69)N-62m / z=521.10(C 33 H 19 N3S2=521.66)N-63m / z=489.15(C 33 H 19 N3O2=489.53)N-64m / z=640.23(C 45 H 28 N4O=640.75)N-65m / z=489.15(C 33 H 19 N3O2=489.53)N-66m / z=505.12(C 33 H 19 N3OS=505.60)N-67m / z=580.17(C 39 H 24 N4S=580.71)N-68m / z=564.20(C 39 H 24 N4O=564.65)N-69m / z=489.15(C 33 H 19 N3O2=489.53)N-70m / z=505.12(C 33 H 19 N3OS=505.60)N-71m / z=505.12(C 33 H 19 N3OS=505.60)N-72m / z=639.24(C 45 H 29 N5=639.76)N-73m / z=607.21(C 42 H 29 N3S=607.78)N-74m / z=715.26(C 52 H 33 N3O=715.86)N-75m / z=640.23(C 45 H28 N4O=640.75)N-76m / z=707.20(C 49 H 29 N3OS=707.85)N-77m / z=591.23(C 42 H 29 N3O=591.71)N-78m / z=617.28(C 45 H 35 N3=617.80)N-79m / z=653.25(C 47 H 31 N3O=653.79)N-80m / z=733.22(C 51 H 31 N3OS=733.89)N-81m / z=615.19(C 43 H 25 N3O2=615.69)N-82m / z=681.19(C 47 H 27 N3OS=681.81)N-83m / z=716.29(C 52 H 36 N4=716.89)N-84m / z=690.24(C 49 H 30 N4O=690.81)N-85m / z=641.25(C 46 H 31 N3O=641.77)N-86m / z=693.22(C 49 H 31 N3S=693.87)N-87m / z=690.24(C 49 H 30 N4O=690.81)N-88m / z=631.17(C 43 H 25 N3OS=631.75)N-89m / z=595.14(C 39 H 21 N3O2S=595.68)N-90m / z=659.24(C 45 H 21 D5N4O2=659.76)N-91m / z=637.16(C 42 H 27 N3S2=637.82)N-92m / z=729.25(C 51 H 31 N5O=729.84)N-93m / z=578.17(C 39 H 22N4O2=578.63)N-94m / z=746.21(C 51 H 30 N4OS=746.89)N-95m / z=681.24(C 48 H 31 N3O2=681.80)N-96m / z=762.19(C 51 H 30 N4S2=762.95)N-97m / z=436.17(C 30 H 20 N4=436.52)N-98m / z=437.16(C 29 H 19 N5=437.51)N-99m / z=513.20(C 35 H 23 N5=513.60)N-100m / z=589.23(C 41 H 27 N5=589.70)N-101m / z=486.18(C 34 H 22 N4=486.58)N-102m / z=527.17(C 35 H 21 N5O=527.59)N-103m / z=589.23(C 41 H 27 N5=589.70)N-104m / z=502.18(C 34 H 22 N4O=502.58)N-105m / z=511.20(C 37 H 25 N3=511.63)N-106m / z=563.21(C 39 H 25 N5=563.66)N-107m / z=511.20(C 37 H 25 N3=511.63)N-108m / z=589.23(C 41 H 27 N5=589.70)N-109m / z=513.20(C 35 H 23 N5=513.60)N-110m / z=462.16(C 30 H 18 N6=462.52)N-111m / z=612.21(C 42 H 24N6=612.70)N-112m / z=499.20(C 36 H 25 N3=499.62)N-113m / z=569.17(C 37 H 23 N5S=569.69)N-114m / z=629.22(C 43 H 27 N5O=629.72)N-115m / z=629.22(C 43 H 27 N5O=629.72)N-116m / z=563.21(C 39 H 25 N5=563.66)N-117m / z=565.2(C 37 H 23 N7=565.64)N-118m / z=630.22(C 42 H 26 N6O=630.71)N-119m / z=611.24(C 45 H 29 N3=611.75)N-120m / z=803.29(C 59 H 37 N3O=803.97)N-121m / z=563.20(C 40 H 25 N3O=563.66)N-122m / z=549.22(C 40 H 27 N3=549.68)N-123m / z=449.15(C 31 H 19 N3O=449.51)N-124m / z=579.18(C 40 H 25 N3S=579.72)N-125m / z=435.17(C 31 H 21 N3=435.53)N-126m / z=435.17(C 31 H 21 N3=435.53)N-127m / z=435.17(C 31 H 21 N3=435.53)N-128m / z=435.17(C 31 H 21 N3=435.53)N-129m / z=435.17(C 31 H 21N3=435.53)N-130m / z=435.17(C 31 H 21 N3=435.53)N-131m / z=435.17(C 31 H 21 N3=435.53)N-132m / z=434.18(C 32 H 22 N2=434.54)N-133m / z=511.20(C 37 H 25 N3=511.63)N-134m / z=611.24(C 45 H 29 N3=611.75)N-135m / z=485.19(C 35 H 23 N3=485.59)N-136m / z=511.2(C 37 H 25 N3=511.63)N-137m / z=511.20(C 37 H 25 N3=511.63)N-138m / z=485.19(C 35 H 23 N3=485.59)N-139m / z=434.18(C 32 H 22 N2=434.54)N-140m / z=434.18(C 32 H 22 N2=434.54)N-141m / z=511.20(C 37 H 25 N3=511.63)N-142m / z=561.22(C 41 H 27 N3=561.69)N-143m / z=587.24(C 43 H 29 N3=587.73)N-144m / z=511.20(C 37 H 25 N3=511.63)N-145m / z=511.20(C 37 H 25 N3=511.63)N-146m / z=511.20(C 37 H 25 N3=511.63)N-147m / z=511.20(C 37 H 25 N3=511.63)N-148m / z=587.24(C43 H 29 N3=587.73)N-149m / z=435.17(C 31 H 21 N3=435.53)N-150m / z=435.17(C 31 H 21 N3=435.53)N-151m / z=435.17(C 31 H 21 N3=435.53)N-152m / z=435.17(C 31 H 21 N3=435.53)N-153m / z=435.17(C 31 H 21 N3=435.53)N-154m / z=435.17(C 31 H 21 N3=435.53)N-155m / z=435.17(C 31 H 21 N3=435.53)N-156m / z=434.18(C 32 H 22 N2=434.54)N-157m / z=485.19(C 35 H 23 N3=485.59)N-158m / z=511.2(C 37 H 25 N3=511.63)N-159m / z=511.20(C 37 H 25 N3=511.63)N-160m / z=511.20(C 37 H 25 N3=511.63)N-161m / z=485.19(C 35 H 23 N3=485.59)N-162m / z=511.20(C 37 H 25 N3=511.63)N-163m / z=485.19(C 35 H 23 N3=485.59)N-164m / z=611.24(C 45 H 29 N3=611.75)N-165m / z=511.20(C 37 H 25 N3=511.63)N-166m / z=511.20(C 37 H 25N3=511.63)N-167m / z=587.24(C 43 H 29 N3=587.73)N-168m / z=587.24(C 43 H 29 N3=587.73)N-169m / z=587.24(C 43 H 29 N3=587.73)N-170m / z=561.22(C 41 H 27 N3=561.69)N-171m / z=511.20(C 37 H 25 N3=511.63)N-172m / z=587.24(C 43 H 29 N3=587.73)N-173m / z=485.19(C 35 H 23 N3=485.59)N-174m / z=485.19(C 35 H 23 N3=485.59)N-175m / z=485.19(C 35 H 23 N3=485.59)N-176m / z=485.19(C 35 H 23 N3=485.59)N-177m / z=485.19(C 35 H 23 N3=485.59)N-178m / z=535.20(C 39 H 25 N3=535.65)N-179m / z=485.19(C 35 H 23 N3=485.59)N-180m / z=485.19(C 35 H 23 N3=485.59)N-181m / z=561.22(C 41 H 27 N3=561.69)N-182m / z=561.22(C 41 H 27 N3=561.69)N-183m / z=561.22(C 41 H 27 N3=561.69)N-184m / z=637.25(C 47 H 31 N3=637.79)N-185m / z=561.22(C41 H 27 N3=561.69)N-186m / z=561.22(C 41 H 27 N3=561.69)N-187m / z=637.25(C 47 H 31 N3=637.79)N-188m / z=637.25(C 47 H 31 N3=637.79)N-189m / z=637.25(C 47 H 31 N3=637.79)N-190m / z=485.19(C 35 H 23 N3=485.59)N-191m / z=485.19(C 35 H 23 N3=485.59)N-192m / z=611.24(C 45 H 29 N3=611.75)N-193m / z=485.19(C 35 H 23 N3=485.59)N-194m / z=485.19(C 35 H 23 N3=485.59)N-195m / z=611.24(C 45 H 29 N3=611.75)N-196m / z=485.19(C 35 H 23 N3=485.59)N-197m / z=485.19(C 35 H 23 N3=485.59)N-198m / z=561.22(C 41 H 27 N3=561.69)N-199m / z=485.19(C 35 H 23 N3=485.59)N-200m / z=485.19(C 35 H 23 N3=485.59)N-201m / z=611.24(C 45 H 29 N3=611.75)N-202m / z=611.24(C 45 H 29 N3=611.75)N-203m / z=485.19(C 35 H 23N3=485.59)N-204m / z=485.19(C 35 H 23 N3=485.59)N-205m / z=485.19(C 35 H 23 N3=485.59)N-206m / z=485.19(C 35 H 23 N3=485.59)N-207m / z=535.20(C 39 H 25 N3=535.65)N-208m / z=535.2(C 39 H 25 N3=535.65)N-209m / z=585.22(C 43 H 27 N3=585.71)N-210m / z=535.2(C 39 H 25 N3=535.65)N-211m / z=585.22(C 43 H 27 N3=585.71)N-212m / z=585.22(C 43 H 27 N3=585.71)N-213m / z=611.24(C 45 H 29 N3=611.75)N-214m / z=611.24(C 45 H 29 N3=611.75)N-215m / z=585.22(C 43 H 27 N3=585.71)N-216m / z=611.24(C 45 H 29 N3=611.75)N-217m / z=687.27(C 51 H 33 N3=687.85)N-218m / z=611.24(C 45 H 29 N3=611.75)N-219m / z=511.20(C 37 H 25 N3=511.63)N-220m / z=611.24(C 45 H 29 N3=611.75)N-221m / z=561.22(C 41 H 27 N3=561.69)N-222m / z=587.24(C43 H 29 N3=587.73)N-223m / z=663.27(C 49 H 33 N3=663.82)N-224m / z=713.28(C 53 H 35 N3=713.88)N-225m / z=575.20(C 41 H 25 N3O=575.67)N-226m / z=601.22(C 43 H 27 N3O=601.71)N-227m / z=700.26(C 51 H 32 N4=700.85)N-228m / z=701.25(C 51 H 31 N3O=701.83)N-229m / z=667.21(C 47 H 29 N3S=667.83)N-230m / z=541.16(C 37 H 23 N3S=541.67)N-231m / z=612.23(C 44 H 28 N4=612.74)N-232m / z=562.22(C 40 H 26 N4=562.68)N-233m / z=689.26(C 49 H 31 N5=689.82)N-234m / z=639.24(C 45 H 29 N5=639.76)N-235m / z=701.25(C 51 H 31 N3O=701.83)N-236m / z=631.17(C 43 H 25 N3OS=631.75)N-237m / z=625.22(C 45 H 27 N3O=625.73)N-238m / z=591.18(C 41 H 25 N3S=591.73)N-239m / z=687.27(C 51 H 33 N3=687.85)N-240m / z=701.25(C 51 H31 N3O=701.83)N-241m / z=619.30(C 45 H 37 N3=619.81)N-242m / z=601.25(C 44 H 31 N3=601.75)N-243m / z=667.23(C 47 H 29 N3O2=667.77)N-244m / z=540.24(C 39 H 20 D5N3=540.68)N-245m / z=521.17(C 35 H 21 F2N3=521.57)N-246m / z=510.18(C 36 H 22 N4=510.60)N-247m / z=652.23(C 46 H 28 N4O=652.76)N-248m / z=527.24(C 38 H 29 N3=527.67)N-249m / z=535.20(C 39 H 25 N3=535.65)N-250m / z=535.20(C 39 H 25 N3=535.65)N-251m / z=535.20(C 39 H 25 N3=535.65)N-252m / z=535.20(C 39 H 25 N3=535.65)N-253m / z=587.24(C 43 H 29 N3=587.73)N-254m / z=612.23(C 44 H 28 N4=612.74)N-255m / z=561.22(C 41 H 27 N3=561.69)N-256m / z=687.27(C 51 H 33 N3=687.85)N-257m / z=663.27(C 49 H 33 N3=663.82)N-258m / z=601.22(C 43 H 27N3O=601.71)N-259m / z=617.19(C 43 H 27 N3S=617.77)N-260m / z=752.29(C 55 H 36 N4=752.92)N-261m / z=651.23(C 47 H 29 N3O=651.77)N-262m / z=677.25(C 49 H 31 N3O=677.81)N-263m / z=541.16(C 37 H 23 N3S=541.67)N-264m / z=750.28(C 55 H 34 N4=750.91)N-265m / z=707.24(C 50 H 33 N3S=707.90)N-266m / z=651.23(C 47 H 29 N3O=651.77)N-267m / z=617.19(C 43 H 27 N3S=617.77)N-268m / z=667.21(C 47 H 29 N3S=667.83)N-269m / z=631.17(C 43 H 25 N3OS=631.75)N-270m / z=767.26(C 55 H 33 N3O2=767.89)N-271m / z=647.15(C 43 H 25 N3S2=647.81)N-272m / z=690.24(C 49 H 30 N4O=690.81)N-273m / z=575.2(C 41 H 25 N3O=575.67)N-274m / z=614.21(C 43 H 26 N4O=614.71)N-275m / z=575.2(C 41 H 25 N3O=575.67)N-276m / z=549.18(C 39 H 23N3O=549.63)N-277m / z=561.22(C 41 H 27 N3=561.69)N-278m / z=566.25(C 41 H 22 D5N3=549.63)N-279m / z=637.25(C 47 H 31 N3=637.79)N-280m / z=644.30(C 47 H 24 D7N3=644.83)N-281m / z=611.24(C 45 H 29 N3=611.75)N-282m / z=611.24(C 45 H 29 N3=611.75)N-283m / z=611.24(C 45 H 29 N3=611.75)N-284m / z=611.24(C 45 H 29 N3=611.75)

[0433] Although synthetic examples of compounds represented by Chemical Formula 1 and Chemical Formula I have been described above, these are all based on the Buchwald-Hartwig cross-coupling reaction, Miyaura boration reaction, Suzuki cross-coupling reaction, Intramolecular acid-induced cyclization reaction (J. Mater. Chem. 1999, 9, 2095), Pd(II)-catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504), and PPh3-mediated reductive cyclization reaction (J. Org. Chem. 2005, 70, 5014), and those skilled in the art will easily understand that the above reaction proceeds even if other substituents defined in Chemical Formula 1 or Chemical Formula I are attached in addition to the substituents specified in the specific synthetic examples.

[0434] Manufacturing evaluation of organic electrical devices

[0435] [Example 1] Red organic electroluminescent device (phosphor host)

[0436] A hole injection layer with a thickness of 10 nm is formed by vacuum depositing N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine (hereinafter referred to as Compound A) and 4,4',4"-((1E,1'E,1"E)-cyclopropane-1,2,3-triylidenetris(cyanomethaneylylidene))tris(2,3,5,6-tetrafluorobenzonitrile) (hereinafter referred to as Compound B) on an ITO layer (anode) formed on a glass substrate. At this time, Compound B is doped such that the weight ratio of Compound A to Compound B is 98:2.

[0437] Subsequently, compound A is vacuum-deposited on the hole injection layer to form a hole transport layer with a thickness of 110 nm.

[0438] Subsequently, N on the aforementioned hole transport layer 7 -(dibenzo[b,d]thiophen-2-yl)-N 2 ,N 2 ,N 7 -triphenyldibenzo[b,d]thiophene-2,7-diamine is vacuum-deposited to form a 10 nm thick light-emitting auxiliary layer.

[0439] Subsequently, a mixture host of the compound P-1 (first host) and the compound N-221 (second host) of the present invention mixed in a weight ratio of 5:5 and a dopant bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate (hereinafter abbreviated as '(piq)2Ir(acac)') are vacuum deposited on the light-emitting auxiliary layer to form a light-emitting layer with a thickness of 30 nm. At this time, the dopant is doped so that the weight ratio of the host to the dopant is 95:5.

[0440] Subsequently, 2-(4'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine is vacuum-deposited on the light-emitting layer to form a hole-blocking layer with a thickness of 10 nm.

[0441] Subsequently, a mixture of 2,7-bis(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalene and (8-quinolinolato)lithium in a weight ratio of 5:5 is vacuum-deposited on the hole-blocking layer to form an electron transport layer with a thickness of 30 nm.

[0442] Subsequently, a compound (8-quinolinolato)lithium is vacuum-deposited on the electron transport layer to form an electron injection layer with a thickness of 0.2 nm, and then Al is deposited to form a cathode with a thickness of 150 nm.

[0443] [Examples 2] to [Examples 38]

[0444] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that the compound of the present invention listed in Table 5 below was used as the host material for the light-emitting layer.

[0445] [Comparative Example 1] to [Comparative Example 4]

[0446] An organic electroluminescent device was fabricated in the same manner as Example 1, except that comparative compounds A to D were used as the first host material for the light-emitting layer.

[0447] <Comparison Compound A> <Comparison Compound B> <Comparison Compound C> <Comparison Compound D>

[0448]

[0449] A forward-bias DC voltage was applied to the organic electroluminescent devices prepared according to Examples 1 to 38 and Comparative Examples 1 to 4 of the present invention, and the electroluminescent (EL) characteristics were measured using a PR-650 from Photoresearch, and 2500 cd / m² 2 T95 was measured at reference brightness using a lifetime measuring device manufactured by MaxScience. The measurement results are shown in Table 5 below.

[0450] This measuring device is not affected by the possibility of daily fluctuations in deposition rate, vacuum quality, or other parameters, and can evaluate new performance by comparing it with a control compound under the same conditions. During the evaluation, since one batch contains four identically prepared OLEDs including a control compound, and the performance of a total of 12 OLEDs across three batches is evaluated individually, the experimental results obtained in this way have statistical significance.

[0451] First host, second host driving voltage / current (mA / cm²) 2 )Luminance (cd / m²) 2)Efficiency (cd / A)T(95) Comparative Example 1 Comparative Compound AN-2215.311.12500.022.691.3 Comparative Example 2 Comparative Compound BN-2215.410.22500.024.497.5 Comparative Example 3 Comparative Compound CN-2215.612.42500.020.192.2 Comparative Example 4 Comparative Compound DN-2215.512.42500.020.190.1 Example 1 P-1N-2214.47.82500.032.2128.4 Example 2 P-5N-2214.57.72500.032.6127.2 Example 3 P-12N-2214.58.02500.031.2130.4 Example 4 P-14N-2214.37.62500.032.7131.0 Example 5 P-17N-2214.47.52500.033.3126.5 Example 6 P-18N-2214.47. 62500.032.7125.8 Example 7 P-24N-2214.37.62500.033.1127.8 Example 8 P-28N-2214.17.22500.034.9134.6 Example 9 P-35N-2214.27.22500.034.6134.0 Example 10 P-39N-2214.37.92500.031.5130.6 Example 11 P-40N-2214.27.32500.034.4133.3 Example 12 P-53N-2214.48.22500.0 30.5129.1 Example 13 P-57N-2214.68.32500.030.1120.3 Example 14 P-58N-2214.57.42500.033.6127.8 Example 15 P-67N-2214.27.32500.034.1133.1 Example 16 P-83N-2214.47.92500.031.6125.6 Example 17 P-90N-2214.57.72500.032.3126.9 Example 18 P-5N-2264.77.72500.032.5 137.8 Example 19 P-14N-2264.67.92500.031.5141.0 Example 20 P-17N-2264.78.22500.030.4136.7 Example 21 P-24N-2264.68.32500.030.3137.9 Example 22 P-28N-2264.47.22500.034.6144.3 Example 23 P-35N-2264.57.32500.034.3143.9 Example 24 P-40N-2264.57.32500.034.1143.7 Example 25 P-53N-2264.67.92500.031.7137.0 Example 26 P-58N-2264.68.12500.030.7138.8 Example 27 P-67N-2714.57.42500.033.9142.5 Example 28 P-5N-2714.7 8.22500.030.6137.1 Example 29 P-12N-2714.77.92500.031.5140.6 Example 30 P-18N-2714.87.62500.033.0136.4 Example 31 P-28N-2714.47.22500.034.8144.6 Example 32P-35N-2714.47.22500.034.5144.0 Example 33P-40N-2714.57.32500.034.2143.8 Example 34P-53N-2714.77.82500.032.0138.2 Example 35P-57N-2714.88.22500.030.4135.2 Example 36P-67N-2714.57.42500.034.0142.8 Example 37P-83N-2714.88.12500.030.9135.2 Example 38P-90N-2714.78.12500.030.9136.8.

[0452] As can be seen from Table 5 above, when the compound of the present invention is used as a host for the light-emitting layer, the driving voltage, efficiency, and lifespan of the organic electroluminescent device can be significantly improved compared to Comparative Examples 1 to 4, which used one of Comparative Compounds A to D, which have a basic framework similar to the compound of the present invention. The compound of the present invention has a tertiary amine structure, and one of the substituents is Ar a is chemical formula A or an aryl group, another substituent is naphthalene substituted with chemical formula B (dibenzothiophene, dibenzofuran), and the remaining one substituent (L 1 -Ar 1 ) is a fluorene group or an aryl group, heterocyclic group, etc. that does not contain a fluorene group.

[0453] Comparative compound A differs in the substituent corresponding to the chemical formula B of the present invention. That is, R in the chemical formula B of the present invention 3Since it cannot form a ring, a 3-condensed ring is substituted on naphthalene, whereas comparative compound A differs in that a 4-condensed ring formed by the condensation of a pentaminous ring to dibenzothiophene is substituted on naphthalene.

[0454] To confirm the difference in energy levels of the compounds due to these differences, T1 values ​​were measured using the DFT Method (B3LYP / 6-31g(D)) of the Gaussian program. The measured values ​​are shown in Table 6 below.

[0455] Comparative compound AP-14T1(eV)2.4712.460

[0456] Referring to Table 6 above, it can be seen that the T1 value of the present invention is lower than that of comparative compound A. Therefore, when the compound of the present invention is used as a host for the light-emitting layer, energy transfer to the dopant is easier compared to comparative compound A, and damage to the dopant during energy transfer is also significantly reduced, so it appears that the driving voltage and lifespan of the device are significantly improved. Comparative compound B also has a different structure corresponding to the chemical formula B of the present invention. That is, in the chemical formula B of the present invention, R 2 , R 3 Since it cannot form a ring with an adjacent group, chemical formula B has a 3-condensed ring structure, whereas comparative compound B differs in that the corresponding substituent is a 5-condensed ring.

[0457] Comparative compound C is R of the present invention 1 In that it is a 3-condensed ring structure in which pyridine is condensed to naphthalene by the substituent corresponding to it forming a heterocycle (pyridine), R 1 This differs from the compounds of the present invention, which are capable of only hydrogen or deuterium and cannot form rings with adjacent groups.

[0458] To confirm the difference in energy levels of the compounds due to these differences, HOMO and LUMO values ​​were measured using the DFT Method (B3LYP / 6-31g(D)) of the Gaussian program. The measured values ​​are shown in Table 7 below.

[0459] Comparative Compound B Comparative Compound CP-5P-53HOMO(eV)-4.911-4.908-4.891-4.853LUMO(eV)-1.466-1.407-1.219-1.280

[0460] Looking at Table 7 above, it can be seen that the HOMO and LUMO values ​​of Compound P-5 and Compound P-53 of the present invention, which are structurally similar to Comparative Compound B and Comparative Compound C, differ. When the compound of the present invention is applied as the first host of the light-emitting layer, it acts as a hole-transporting host that transmits holes from the hole transport region. In the case of Comparative Compound B and Comparative Compound C, the LUMO energy level is formed deeply, so electrons are injected more easily from the electron transport region, weakening the hole transport characteristics of the compound itself, and as a result, it fails to properly perform the hole transport role intended as the first host.

[0461] On the other hand, the compound of the present invention has a larger LUMO value (shallow) compared to comparative compound B and comparative compound C, so it has excellent energy transfer ability to dopants by receiving holes from the hole transport region and balances with the electron transport characteristics of the second host, thereby maximizing charge balance and improving the characteristics of the device.

[0462] Comparative compound D is structurally similar to the compound of the present invention, but differs from the compound of the present invention in that the substituent corresponding to Ar1 of the present invention is fluorene and contains an aromatic ring other than a six-membered ring.

[0463] Comparative compound D has poor packing properties compared to the compound of the present invention because the intermolecular distance increases during device deposition and the intramolecular or intermolecular π-π interactions are weakened compared to the compound of the present invention. On the other hand, compared to comparative compound D, the compound of the present invention has planar molecules, so it appears that the characteristics of the device are improved when it is used as a host.

[0464] From Tables 5 to 7 above, it can be confirmed that even among compounds with similar compositions, the compounds of the present invention that satisfy all complex factors such as the type of substituent and the substitution position of the substituent exhibit a significant effect in organic electrical devices compared to other comparative compounds, and through this, it can be seen that the compounds of the present invention exhibit a significant effect in organic electrical devices compared to simple structural isomers or other compounds with similar compositions not described in this specification.

[0465] These results suggest that even for compounds with similar molecular components, properties such as hole characteristics, photoelectric efficiency, energy levels, hole injection and mobility characteristics, hole-electron charge balance, volume density, and intermolecular distance can vary significantly and unpredictably depending on the type and position of the substituents. Furthermore, they indicate that device performance may vary due to complex factors rather than being influenced by a single configuration alone.

[0466] The foregoing description is merely illustrative of the present invention, and those skilled in the art to which the present invention pertains will be able to make various modifications without departing from the essential characteristics of the present invention. The scope of protection of the present invention shall be interpreted by the claims below, and all technology within an equivalent scope shall be interpreted as being included within the scope of rights of the present invention.

Claims

1. Compound represented by the following chemical formula 1: <Chemical Formula 1> <Chemical Formula A> <Chemical Formula B> In the above chemical formula 1, Ar a is chemical formula A or C6~C 60 It is an aryl group, and in chemical formula A, * indicates a binding site, Ar b is chemical formula B, where * represents a binding site, and Ar 1 C6~C 60 aryl group of; or C2~C comprising at least one heteroatom among O, N, S, Si and P 60 It is a heterocyclic ring of, and L 1 is a single bond; C6~C 60 arylene group of; and C2~C comprising at least one heteroatom among O, N, S, Si and P. 60 It is selected from a group consisting of heterocycles, X is NR 5 , O or S and, Y is O or S, The C ring and the D ring are C6~C, respectively. 60 an aromatic ring; or a C2~C group comprising at least one heteroatom among O, N, S, Si, and P. 60 It is a heterocyclic ring, and the C ring and D ring each have one or more identical or distinct R 4 It can be replaced with, R 1 It is hydrogen or deuterium, and R 2 to R 4 They are independently hydrogen; deuterium; halogen; cyano group; C6~C 60 aryl group of; C2~C comprising at least one heteroatom among O, N, S, Si, and P 60 The heterocyclic ring of; C3~C 60 aliphatic ring; C6~C 60 The aromatic ring and C3~C 60 Fusion ring of the aliphatic ring; C1~C 20 alkyl group of; C2~C 20 The Alken Diary of; C2~C 20 Alkin's Diary; C1~C 20 alkoxy groups; and C6~C 60 It is selected from the group consisting of aryloxy groups, and R 5 is C6~C 60 aryl group of; C2~C comprising at least one heteroatom among O, N, S, Si, and P 60 The heterocyclic ring of; C3~C 60 aliphatic ring of; and C6~C 60 The aromatic ring and C3~C 60 It is selected from a group consisting of fused rings of aliphatic rings, and a is an integer from 0 to 6, b is an integer from 0 to 3, and c is an integer from 0 to 4, and However, the above aryl group, arylene group, and aromatic ring are single rings or condensed rings composed only of six-membered rings, and The above aryl group, arylene group, aromatic ring, heterocyclic group, aliphatic ring, fused ring, alkyl group, alkenyl group, alkyneyl group, alkoxy group, and aryloxy group are each deuterium; halogen; C1-C 20 alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; C1-C 20 alkoxy group of; C6-C 30 aryloxy group of; C1-C 20 alkyl group of; C2-C 20 alkene diary; C2-C 20 Alkin's Diary; C6-C 30 aryl group of; C6-C substituted with deuterium 30 aryl group of; C3-C 30 Aliphatic ring; C6-C 30 The aromatic ring and C3-C 30 A fused ring of an aliphatic ring; and a C2-C comprising at least one heteroatom among O, N, S, Si, and P. 30 It can be substituted with one or more substituents selected from the group consisting of heterocyclic rings, and the hydrogen of the substituent can be replaced with deuterium.

2. In Paragraph 1, A compound characterized in that the above C ring is selected from the group consisting of the following chemical formulas C-1 to C-15: <Chemical Formula C-1> <Chemical Formula C-2> <Chemical Formula C-3> <Chemical Formula C-4> <Chemical Formula C-5> <Chemical Formula C-6> <Chemical Formula C-7> <Chemical Formula C-8> <Chemical Formula C-9> <Chemical Formula C-10> <Chemical Formula C-11> <Chemical Formula C-12> <Chemical Formula C-13> <Chemical Formula C-14> <Chemical Formula C-15> In the above chemical formulas C-1 to C-15, v represents a site condensed to the X-containing 5-membered ring of chemical formula A, and R 4 is as defined in paragraph 1, where d is an integer from 0 to 3, e is an integer from 0 to 5, and f is an integer from 0 to 7.

3. In Paragraph 1, A compound characterized in that the above D ring is selected from the group consisting of the following chemical formulas D-1 to D-11: <Structural Formula D-1> <Structural Formula D-2> <Structural Formula D-3> <Structural Formula D-4> <Structural Formula D-5> <Structural Formula D-6> <Structural Formula D-7> <Structural Formula D-8> <Structural Formula D-9> <Structural Formula D-10> <Structural Formula D-11> In the above chemical formulas D-1 to D-11, v represents the site condensed to the X-containing 5-membered ring of chemical formula A, and W is NR 6 , O or S and, R 4 is hydrogen; deuterium; C6~C 60 aryl group of; C2~C comprising at least one heteroatom among O, N, S, Si, and P 60 The heterocyclic group of; and C1~C 20 Selected from the group consisting of alkyl groups, R 6 Hydrogen; Deuterium; C6~C 30 aryl group of; C2~C comprising at least one heteroatom among O, N, S, Si, and P 30 The heterocyclic group of; and C1~C 20 Selected from the group consisting of alkyl groups, d is an integer from 0 to 4, e is an integer from 0 to 6, f is an integer from 0 to 8, and g is an integer from 0 to 6.

4. In Paragraph 1, A compound characterized in that the above chemical formula B is one of the following chemical formulas B-1 to B-4: <Structural Formula B-1> <Structural Formula B-2> <Structural Formula B-3> <Structural Formula B-4> In the above chemical formulas B-1 to B-4, Y is O or S, R 2 and R 3 Hydrogen; deuterium; C6~C independently 30 aryl group of; C2~C comprising at least one heteroatom among O, N, S, Si, and P 30 The heterocyclic group of; and C1~C 20 Selected from the group consisting of alkyl groups, where b and c are as defined in claim 1.

5. In Paragraph 1, The above Ar 1 In the case where this is an aryl group, the aryl group is selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, triphenylene, and combinations thereof, and The above L 1 A compound characterized in that, in the case of this arylene group, the arylene group is selected from the group consisting of phenylene, naphthylene, biphenyl, terphenyl, phenanthrene, and triphenylene.

6. A material for an organic electrical device containing the compound of claim 1 and a compound represented by the following chemical formula I: <Chemical Formula I> In the above chemical formula I, X A To X C is N or C(R'), at least one of them is N, and Ar A or Ar C C6~C are independent of each other 60 aryl group; fluorenyl group; C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic ring of; C3~C 60 aliphatic ring; C3~C 60 The aliphatic ring and C6~C 60 The fused ring of the aromatic ring; and C1~C 30 Selected from the group consisting of alkyl groups, L A to L C are independent single bonds; C6~C 60 arylene group; fluorenyllene group; C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic ring of; C3~C 60 aliphatic ring of; and C3~C 60 The aliphatic ring and C6~C 60 It is selected from a group consisting of fused rings of aromatic rings, and The above R' is hydrogen; deuterium; halogen; cyano group; nitro group; C6~C 60 aryl group; fluorenyl group; C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic ring of; C3~C 60 aliphatic ring; C6~C 60 The aromatic ring and C3~C 60 Fusion ring of the aliphatic ring; C1~C 20 alkyl group of; C2~C 20 The Alken Diary of; C2~C 20 Alkin's Diary; C1~C 20 alkoxy groups; and C6~C 60 It is selected from the group consisting of aryloxy groups, and The above aryl group, arylene group, fluorenyl group, fluorenyllene group, heterocyclic group, aliphatic cycle, fused cycle, alkyl group, alkenyl group, alkyneyl group, alkoxy group, and aryloxy group are each deuterium; halogen; C1-C 20 alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; nitro group; C1-C 20 alkylthio group of; C1-C 20 alkoxy group of; C6-C 30 aryloxy group of; C6-C 30 aryl thiologic; C1-C 20 alkyl group of; C2-C 20 alkene diary; C2-C 20 Alkin's Diary; C6-C 30 aryl group; fluoreneyl group; C3-C 30 Aliphatic ring; C6-C 30 The aromatic ring and C3-C 30 A fused ring of an aliphatic ring; and a C2-C comprising at least one heteroatom among O, N, S, Si, and P. 30 It can be substituted with one or more substituents selected from a group of heterocyclic rings, and adjacent substituents can bond with each other to form a ring, and the hydrogen of the substituent can be replaced with deuterium.

7. In Paragraph 6, The above Ar A or Ar C A material for an organic electrical device characterized in that at least one of the following is selected from the group consisting of the chemical formulas Ar-a to Ar-d: <Chemical Formula Ar-a> <Chemical Formula Ar-b> <Chemical Formula Ar-c> <Chemical Formula Ar-d> In the above chemical formulas Ar-a to Ar-d, Y A to Y C O, S, C(R) are independent of each other 21 )(R 22 ) or N(Ar 11 ) and, R A to R F , R 21 and R 22 are independently hydrogen; deuterium; halogen; C1-C 20 alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; nitro group; C1-C 20 alkylthio group of; C1-C 20 alkoxy group of; C6-C 30 aryloxy group of; C6-C 30 aryl thiologic; C1-C 20 alkyl group of; C2-C 20 alkene diary; C2-C 20 Alkin's Diary; C6-C 30 aryl group; fluorenyl group; C2-C comprising at least one heteroatom among O, N, S, Si, and P 30 heterocyclic; C3-C 30 aliphatic ring of; and C6-C 30 The aromatic ring and C3-C 30 It is selected from a group consisting of fused rings of aliphatic rings, and neighboring groups can combine with each other to form rings, and R 21 and R 22 They can combine with each other to form a ring, Ar 11 C1-C 20 alkyl group of; C6-C 30 aryl group; fluorenyl group; C2-C comprising at least one heteroatom among O, N, S, Si, and P 30 heterocyclic; C3-C 30 aliphatic ring of; and C6-C 30 The aromatic ring and C3-C 30 Selected from a group consisting of fused rings of aliphatic rings, ta and tc are integers from 0 to 3, tb and td are integers from 0 to 4, te is an integer from 0 to 5, and tf is an integer from 0 to 7, and The above R A to R F , R1, R2, Ar 11 deuterium; halogen; C1-C, respectively. 20 alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; nitro group; C1-C 20 alkylthio group of; C1-C 20 alkoxy group of; C6-C 30 aryloxy group of; C6-C 30 aryl thiologic; C1-C 20 alkyl group of; C2-C 20 alkene diary; C2-C 20 Alkin's Diary; C6-C 30 aryl group; fluorenyl group; C2-C comprising at least one heteroatom among O, N, S, Si, and P 30 heterocyclic; C3-C 30 aliphatic ring of; and C6-C 30 The aromatic ring and C3-C 30 It can be substituted with one or more substituents selected from the group consisting of fused rings of the aliphatic ring, and the hydrogen of the substituent can be replaced with deuterium.

8. An organic electric device comprising a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, wherein An organic electric device characterized in that the above organic layer comprises the compound of claim 1 or the material for an organic electric device of claim 6.

9. In Paragraph 8, An organic electric device characterized in that the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound of claim 1 or the organic electric device material of claim 6.

10. In Paragraph 8, An organic electric device characterized in that the organic layer comprises two or more stacks including a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on the first electrode.

11. A display device comprising the organic electric element of claim 8; and An electronic device including a control unit for driving the above-mentioned display device.

12. In Paragraph 11, The above electronic device is characterized as being a wired or wireless communication terminal.

13. In Paragraph 12, An electronic device characterized in that the above-mentioned wired / wireless communication terminal is a mobile communication terminal, navigation system, game console, TV, or computer.

14. A step of depositing an organic layer material comprising a compound represented by Chemical Formula 1 of Claim 1; A step of recovering the organic layer material attached to the deposition equipment; and A method for recovering a compound characterized by including the step of purifying the recovered organic layer material to obtain a compound represented by Chemical Formula 1 having a purity of 99.9% or higher.

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