Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof

Abstract

The present invention provides a novel compound capable of improving the luminous efficiency, stability, and lifespan of a device, an organic electric device using the same, and an electronic device thereof.

Description

Technology Field

[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. Background Technology

[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 comprising 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 enhance the efficiency and stability of the organic electrical device; for example, it may consist of a hole injection layer, a hole transport layer, an emissive layer, an electron transport layer, and an electron injection layer.

[0003] Materials used as organic layers in organic electrical 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.

[0004] The most critical issues regarding organic light-emitting diodes (OLEDs) are lifespan and efficiency. As displays become larger in size, these efficiency and lifespan issues must be resolved. Efficiency, lifespan, and driving voltage are interconnected; 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.

[0005] However, simply improving the aforementioned organic layers does not guarantee maximum efficiency. This is because both a 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 (mobility, interfacial characteristics, etc.), form an optimal combination.

[0006] Furthermore, in order to solve the light emission problem in the hole transport layer of organic electroluminescent devices, an auxiliary light-emitting layer must exist between the hole transport layer and the light-emitting layer, and it is now necessary to develop different auxiliary light-emitting layers according to each light-emitting layer (R, G, B).

[0007] Generally, electrons are transferred from the electron transport layer to the light-emitting layer, and holes are transferred from the hole transport layer to the light-emitting layer, and excitons are generated by recombination.

[0008] However, materials used in the hole transport layer must have a low HOMO value, so most of them have a low T1 value. As a result, excitons generated in the emissive layer move into the hole transport layer, causing charge unbalance within the emissive layer and consequently emitting light at the hole transport layer interface.

[0009] When light is emitted at the interface of the hole transport layer, problems arise such as reduced color purity and efficiency of the organic device and a shortened lifespan. Therefore, there is an urgent need to develop an emitting auxiliary layer that has a high T1 value and a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the emitting layer.

[0010] Meanwhile, there is a need to develop hole injection layer materials that possess high glass transition temperatures, which delay the penetration and diffusion of metal oxides from the anode electrode (ITO) into the organic layer—one of the causes of shortened lifespan in organic electronic devices—while also exhibiting stable characteristics against Joule heating generated during device operation. It has been reported that the low glass transition temperatures of hole transport layer materials degrade the uniformity of the thin film surface during device operation, which significantly impacts device lifespan. Furthermore, as OLED devices are primarily formed by deposition methods, there is a need to develop materials capable of withstanding prolonged deposition, specifically materials with strong heat resistance.

[0011] In other words, to fully realize the excellent characteristics of organic electronic devices, it is essential that the materials forming the organic layer within the device—such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, and light-emitting auxiliary layer materials—be supported by stable and efficient materials. However, the development of stable and efficient organic layer materials for organic electronic devices has not yet been sufficiently achieved. Therefore, the development of new materials continues to be required. The problem to be solved

[0012] In order to solve the problems of the aforementioned background technology, the present invention has identified a compound having a novel structure and has also revealed that when this compound is applied to an organic electric device, the luminous efficiency, stability, and lifespan of the device can be significantly improved.

[0013] Accordingly, the present invention aims to provide a novel compound, an organic electric device using the same, and an electronic device thereof. means of solving the problem

[0014] The present invention provides a compound represented by the following chemical formula 1.

[0015] <Chemical Formula 1>

[0016]

[0017] In another aspect, the present invention provides an organic electric element and an electronic device comprising a compound represented by the above chemical formula 1. Effects of the invention

[0018] By using the compound according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the device can be achieved, and the color purity and lifespan of the device can be significantly improved. Brief explanation of the drawing

[0019] FIGS. 1 to 3 are exemplary diagrams of an organic electroluminescent device according to the present invention. FIG. 4 shows a chemical formula according to one aspect of the present invention. Specific details for implementing the invention

[0020] The present invention will be described in detail below with reference to embodiments thereof. In describing the present invention, if it is determined that a detailed description of related known components or functions may obscure the essence of the invention, such detailed description will be omitted.

[0021] In addition, terms such as first, second, A, B, (a), (b), etc., may be used when describing the components of the present invention. These terms are intended only to distinguish the components from other components, and the essence, order, or sequence of the components is not limited by the terms. Where it is stated that a component is "connected," "combined," or "connected" to another component, it should be understood that the component may be directly connected or connected to the other component, but that another component may also be "connected," "combined," or "connected" between each component.

[0022] As used in this specification and the appended claims, unless otherwise noted, the meanings of the following terms are as follows:

[0023] As used herein, the terms “halo” or “halogen” are fluorine (F), bromine (Br), chlorine (Cl), or iodine (I) unless otherwise noted.

[0024] Unless otherwise noted, the terms “alkyl” or “alkyl group” as used in the present invention refer to radicals of saturated aliphatic functional groups having single bonds of 1 to 60 carbon atoms, including straight-chain alkyl groups, branched-chain alkyl groups, cycloalkyl (alicyclic) groups, alkyl-substituted cycloalkyl groups, and cycloalkyl-substituted alkyl groups.

[0025] Unless otherwise stated, the terms “alkenyl group,” “alkenyl group,” or “alkynyl group” as used in the present invention each have a double or triple bond having 2 to 60 carbon atoms and include a straight or side chain group, but are not limited thereto.

[0026] The term "cycloalkyl" as used in the present invention means an alkyl group forming a ring having 3 to 60 carbon atoms, unless otherwise explained, but is not limited thereto.

[0027] The terms “alkyxyl group,” “alkoxy group,” or “alkyloxy group” used in the present invention refer to an alkyl group to which an oxygen radical is attached, and unless otherwise described, have 1 to 60 carbon atoms, but are not limited thereto.

[0028] The terms “aryloxyl group” or “aryloxy group” used in the present invention refer to an aryl group to which an oxygen radical is attached, and unless otherwise explained, have 6 to 60 carbon atoms, but are not limited thereto.

[0029] Unless otherwise noted, the terms "aryl group" and "arylene group" as used in the present invention each have 6 to 60 carbon atoms, but are not limited thereto. In the present invention, an aryl group or an arylene group refers to a single-ring or multi-ring aromatic group and includes an aromatic ring formed by an adjacent substituent participating in bonding or reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

[0030] The prefixes "aryl" or "ar" denote radicals substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, an arylalkenyl group is an alkenyl group substituted with an aryl group, and radicals substituted with an aryl group have the number of carbon atoms described in this specification.

[0031] In addition, when prefixes are named consecutively, it means that the substituents are listed in the order in which they were first described. For example, "aryl alkoxy" refers to an alkoxy group substituted with an aryl group; "alkoxyl carbonyl" refers to a carbonyl group substituted with an alkoxyl group; and "aryl carbonyl alkenyl" refers to an alkhenyl group substituted with an aryl carbonyl group, where the aryl carbonyl group is a carbonyl group substituted with an aryl group.

[0032] The term "heterocyclic ring" as used in the present invention comprises one or more heteroatoms, has a carbon number of 2 to 60, comprises at least one of a single ring and a multi-ring, and comprises a heteroaliphatic ring and a heteroaromatic ring. It may also be formed by the bonding of adjacent functional groups.

[0033] As used herein, the term "heteroatom" refers to N, O, S, P, or Si unless otherwise noted.

[0034] Additionally, "heterocyclic rings" may include rings containing SO2 instead of the ring-forming carbon. For example, "heterocyclic rings" include the following compounds.

[0035]

[0036] Unless otherwise noted, the terms “fluorenyl group” or “fluorenyl group” used in the present invention refer to a monovalent or divalent functional group in which R, R’ and R” are all hydrogen in the following structure, respectively, and “substituted fluorenyl group” or “substituted fluorenyl group” refers to a case in which at least one of the substituents R, R’, and R” is a substituent other than hydrogen, and includes cases in which R and R’ are bonded to each other to form a spiro compound together with the carbon to which they are bonded.

[0037]

[0038] The term "spiro compound" used in the present invention has a "spiro union," and a spiro union refers to a connection formed by two rings sharing only one atom. At this time, the atom shared between the two rings is called a "spiro atom," and depending on the number of spiro atoms contained in a compound, they are respectively called "monospiro-," "dyspiro-," and "trispiro-" compounds.

[0039] Unless otherwise stated, the term “aliphatic” as used in the present invention means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and “aliphatic ring” means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

[0040] Unless otherwise stated, the term “ring” as used in the present invention refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heteroring having 2 to 60 carbon atoms, or a combination thereof, and includes saturated or unsaturated rings.

[0041] Other heterocompounds or heteroradicals other than the aforementioned heterocompounds comprise one or more heteroatoms, but are not limited thereto.

[0042] Additionally, unless explicitly stated otherwise, in the terms "substituted or unsubstituted" as used in this invention, "substituted" refers to deuterium, halogen, amino group, nitrile group, nitro group, C1~C 20 alkyl group of, C1~C 20 alkoxyl group of, C1~C 20 alkylamine group of, C1~C 20 alkylthiophene group of, C6~C 20 arylthiophene group, C2~C 20 The Alken Diary, C2~C 20 Alkin's Diary, C3~C 20 cycloalkyl group of, C6~C 20 aryl group, C6~C substituted with deuterium 20 aryl group of, C8~C 20aryl alkenyl group, silane group, boron group, germanium group, and C2~C 20 It means that it is substituted with one or more substituents selected from the group of heterocyclic rings, but is not limited to these substituents.

[0043] 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.

[0044]

[0045] Here, if a is an integer of 0, the substituent R 1 ... does not exist, and if a is an integer of 1, there is 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 bonds as follows, respectively, where R 1 The atoms may be identical or different from each other, and when a is an integer from 4 to 6, they are bonded to the carbons of the benzene ring in a similar manner, while the indication of the hydrogen bonded to the carbons forming the benzene ring is omitted.

[0046]

[0048] Hereinafter, a compound according to one aspect of the present invention and an organic electric device including the same will be described.

[0050] The present invention provides a compound represented by the following chemical formula 1.

[0051] <Chemical Formula 1>

[0052]

[0053] In the above chemical formula 1, each symbol can be defined as follows.

[0054] 1) Ar 1 and Ar 2 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 P60 The heterocyclic ring of; C3~C 60 The aliphatic ring and C6~C 60 Fusion ring of the aromatic ring; C1~C 60 alkyl group of; C2~C 20 The Alken Diary of; C2~C 20 Alkin's Diary; C1~C 30 alkoxyl groups of; and C6~C 30 Selected from the group consisting of the aryloxy group of; and Ar 1 and Ar 2 They cannot combine with each other to form a ring.

[0055] Ar 1 and Ar 2 If it is an aryl group, preferably C6~C 30 The aryl group of, more preferably C6~C 24 The aryl group of can be, for example, phenylene, biphenyl, naphthalene, terphenyl, etc.

[0056] Ar 1 and Ar 2 If it is a heterocyclic ring, preferably C2~C 30 The heterocyclic group of, more preferably C2~C 24 It may be a heterocyclic group, and examples include pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazolin, benzoquinazolin, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc.

[0057] Ar 1 and Ar 2 In the case of a fused ring, preferably C3~C 30 The aliphatic ring and C6~C 30 The fusion ring of the aromatic ring, more preferably C3~C 24 The aliphatic ring and C6~C 24 It may be a fused ring of an aromatic ring.

[0058] Ar 1 and Ar 2If is an alkyl group, preferably C1 to C 30 It may be an alkyl group, and more preferably C1 to C 24 It can be an alkyl group.

[0059] Ar 1 and Ar 2 In the case where is an alkoxyl group, preferably C1~C 24 It can be an alkoxyl group.

[0060] Ar 1 and Ar 2 If is an aryloxy group, preferably C1~C 24 It can be an aryloxy group.

[0061] 2) Ar 3 and Ar 4 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 The aliphatic ring and C6~C 60 Fusion ring of the aromatic ring; C1~C 60 alkyl group of; C2~C 20 The Alken Diary of; C2~C 20 Alkin's Diary; C1~C 30 alkoxyl groups of; and C6~C 30 It is selected from the group consisting of aryloxy groups.

[0062] Ar 3 and Ar 4 If it is an aryl group, preferably C6~C 30 The aryl group of, more preferably C6~C 24 The aryl group of can be, for example, phenylene, biphenyl, naphthalene, terphenyl, etc.

[0063] Ar 3 and Ar 4 If it is a heterocyclic ring, preferably C2~C 30 The heterocyclic group of, more preferably C2~C 24It may be a heterocyclic group, and examples include pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazolin, benzoquinazolin, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc.

[0064] Ar 3 and Ar 4 In the case of a fused ring, preferably C3~C 30 The aliphatic ring and C6~C 30 The fusion ring of the aromatic ring, more preferably C3~C 24 The aliphatic ring and C6~C 24 It may be a fused ring of an aromatic ring.

[0065] Ar 3 and Ar 4 If is an alkyl group, preferably C1 to C 30 It may be an alkyl group, and more preferably C1 to C 24 It can be an alkyl group.

[0066] Ar 3 and Ar 4 In the case where is an alkoxyl group, preferably C1~C 24 It can be an alkoxyl group.

[0067] Ar 3 and Ar 4 If is an aryloxy group, preferably C1~C 24 It can be an aryloxy group.

[0068] 3) L 1 C6~C 60 arylene group; fluorenyllene group; C3~C 60 The aliphatic ring and C6~C 60 The fused ring of the aromatic ring; and C2~C 60 It is selected from a group consisting of heterocyclic rings.

[0069] L 1 In the case where it is an arylene group, preferably C6~C 30The arylene group of, more preferably C6~C 24 It can be an arylene group, for example, phenylene, biphenyl, naphthalene, terphenyl, etc.

[0070] L 1 If it is a heterocyclic ring, preferably C2~C 30 The heterocyclic group of, more preferably C2~C 24 It may be a heterocyclic group, and examples include pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazolin, benzoquinazolin, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc.

[0071] L 1 In the case of a fused ring, preferably C3~C 30 The aliphatic ring and C6~C 30 The fusion ring of the aromatic ring, more preferably C3~C 24 The aliphatic ring and C6~C 24 It may be a fused ring of an aromatic ring.

[0072] 4) R 1 and R 2 Each is identical or different and independently hydrogen; deuterium; tritium; 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 The aliphatic ring and C6~C 60 Fusion ring of the aromatic ring; C1~C 50 alkyl group of; C2~C 20 The Alken Diary of; C2~C 20 Alkin's Diary; C1~C 30 alkoxyl group of; C6~C 30 The aryloxy group of; and -L'-N(R a )(R bSelected from a group consisting of ); and adjacent multiple R 1 Among themselves, or multiple Rs 2 They can combine with each other to form a ring.

[0073] R 1 and R 2 If it is an aryl group, preferably C6~C 30 The aryl group of, more preferably C6~C 24 The aryl group of can be, for example, phenylene, biphenyl, naphthalene, terphenyl, etc.

[0074] R 1 and R 2 If it is a heterocyclic ring, preferably C2~C 30 The heterocyclic group of, more preferably C2~C 24 It may be a heterocyclic group, and examples include pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazolin, benzoquinazolin, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc.

[0075] R 1 and R 2 In the case of a fused ring, preferably C3~C 30 The aliphatic ring and C6~C 30 The fusion ring of the aromatic ring, more preferably C3~C 24 The aliphatic ring and C6~C 24 It may be a fused ring of an aromatic ring.

[0076] R 1 and R 2 If is an alkyl group, preferably C1 to C 30 It may be an alkyl group, and more preferably C1 to C 24 It can be an alkyl group.

[0077] R 1 and R 2 In the case where is an alkoxyl group, preferably C1~C 24 It can be an alkoxyl group.

[0078] R 1 and R 2 If is an aryloxy group, preferably C1~C 24 It can be an aryloxy group.

[0079] 5) The above L' is a single bond; C6~C 60 arylene group; fluorenyllene group; C3~C 60 an aliphatic ring of; C2~C comprising at least one heteroatom among O, N, S, Si, and P. 60 A heterocyclic group of; and selected from a group consisting of combinations thereof, wherein R a and R b C6~C are independent of each other 60 aryl group; fluorene group; C3~C 60 an aliphatic ring of; C2~C comprising at least one heteroatom among O, N, S, Si, and P. 60 It is selected from a group consisting of heterocyclic rings; and combinations thereof.

[0080] When L' is an arylene group, preferably C6~C 30 The arylene group of, more preferably C6~C 24 It can be an arylene group, for example, phenylene, biphenyl, naphthalene, terphenyl, etc.

[0081] If L' is a heterocyclic ring, preferably C2~C 30 The heterocyclic group of, more preferably C2~C 24 It may be a heterocyclic group, and examples include pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazolin, benzoquinazolin, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc.

[0082] If L' is an aliphatic ring, preferably C3~C 30 The aliphatic ring of, more preferably C3~C 24It could be a local aliphatic ring.

[0083] R a and R b In the case of an aryl group, C6~C 30 It is preferable that it be an aryl group, and most preferably C6~C 25 It can be an aryl group, and examples include phenyl, biphenyl, naphthyl, phenanthrene, terphenyl, etc.

[0084] R a and R b If it is a heterocyclic ring, preferably C2~C 30 The heterocyclic group of, more preferably C2~C 24 It may be a heterocyclic group, and examples include pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazolin, benzoquinazolin, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc.

[0085] R a and R b In the case of an aliphatic ring, preferably C3~C 30 The aliphatic ring of, more preferably C3~C 24 It could be a local aliphatic ring.

[0086] 5) R 3 It contains hydrogen; deuterium; tritium; halogen; and C1~C 50 It is selected from the group consisting of the alkyl group of.

[0087] R 3 In the case where it is an alkyl group, preferably C1 to C 30 It may be an alkyl group, and more preferably C1 to C 24 It can be an alkyl group.

[0088] 6) a is an integer from 0 to 4, b is an integer from 0 to 3, and c is an integer from 0 to 5.

[0089] 7) Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenyllene group, aliphatic cyclic group, fused cyclic group, alkyl group, alkenyl group, alkoxy group, and aryloxy group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 alkylthio group of; C1~C 20 alkoxy groups; C1~C 20 alkyl group of; C2~C 20 The Alken Diary of; C2~C 20 Alkin's Diary; C6~C 20 aryl group of; C6~C substituted with deuterium 20 aryl group; fluorene group; C2~C 20 The heterocyclic ring of; C3~C 20 cycloalkyl group of; C7~C 20 arylalkyl group of; C8~C 20 The aryl alkene group of; and -L'-N(R a )(R b It may be further substituted with one or more substituents selected from the group consisting of ); and these substituents may also combine with each other to form a ring, where 'ring' refers to C3~C 60 aliphatic ring of or C6~C 60 aromatic ring or C2~C 60 It refers to a fused ring composed of a heterocycle or a combination thereof, and includes saturated or unsaturated rings.

[0091] In addition, the present invention provides a compound represented by the above chemical formula 1 that is represented by any one of the following chemical formulas 1-1 to 1-4.

[0092] <Chemical Formula 1-1> <Chemical Formula 1-2>

[0093]

[0094] <Chemical Formula 1-3> <Chemical Formula 1-4>

[0095]

[0096] {In the above chemical formulas 1-1 to 1-4, Ar 1 , Ar 2 , Ar 3 , Ar 4 , L 1 , R 1 , R 2 , R 3 , a, b, and c are as defined in Chemical Formula 1 above.

[0098] In addition, the present invention provides a compound represented by the following chemical formula 2, wherein the compound represented by the above chemical formula 1 is a compound represented by the above chemical formula 2.

[0099] <Chemical Formula 2>

[0100]

[0101] In the above chemical formula 2,

[0102] 1) Ar 1 , Ar 2 , Ar 3 , Ar 4 , R 1 , R 2 , R 3 , a, b, and c are the same as defined in Chemical Formula 1 above, and

[0103] 2) R 4 is R of the above chemical formula 1 1 Identical to the definition of and adjacent multiple R 4 They can combine with each other to form a ring,

[0104] 3) d is an integer from 0 to 3.

[0106] In addition, the present invention provides a compound represented by the following chemical formula 3, wherein the compound represented by the above chemical formula 1 is a compound represented by the following chemical formula 3.

[0107] <Chemical Formula 3>

[0108]

[0109] In the above chemical formula 3,

[0110] 1) Ar 1 , Ar 2 , Ar 4, R 1 , R 2 , R 3 , a, b, and c are the same as defined in Chemical Formula 1 above, and

[0111] 2) R 4 and d are the same as defined in the above chemical formula 2, and

[0112] 3) R 5 is R of the above chemical formula 1 1 Identical to the definition of, and adjacent multiple R 5 They can combine with each other to form a ring,

[0113] 4) e is an integer from 0 to 5.

[0115] In addition, the present invention provides a compound in which the compound represented by the above chemical formula 1 is represented by the following chemical formula 4.

[0116] <Chemical Formula 4>

[0117]

[0118] In the above chemical formula 4,

[0119] 1) Ar 1 , Ar 2 , Ar 4 , R 1 , R 2 , R 3 , a, b, and c are the same as defined in Chemical Formula 1 above, and

[0120] 2) R 4 and d are the same as defined in the above chemical formula 2, and

[0121] 3) R 5 and e are the same as defined in Chemical Formula 3 above.

[0123] In addition, the present invention provides a compound represented by the above chemical formula 1 that is represented by any one of the following chemical formulas 4-1 to 4-3.

[0124] <Chemical Formula 4-1> <Chemical Formula 4-2> <Chemical Formula 4-3>

[0125]

[0126] {In the above chemical formulas 4-1 to 4-3,

[0127] 1) Ar 1 , Ar 2 , Ar 4 , R 1 , R 2 , R 3 , a, b, and c are the same as defined in Chemical Formula 1 above, and

[0128] 2) R 4 and d are the same as defined in the above chemical formula 2, and

[0129] 3) R 5 and e are the same as defined in Chemical Formula 3 above.

[0131] In addition, the present invention provides a compound represented by the above chemical formula 1, which is represented by any one of the following compounds P-1 to P-123.

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0164] Referring to FIG. 1, the organic electric device (100) according to the present invention comprises a first electrode (110), a second electrode (170), and an organic layer between the first electrode (110) and the second electrode (170) comprising a single compound represented by Chemical Formula 1 or two or more compounds. At this time, the first electrode (110) may be an anode or a positive electrode, and the second electrode (170) may be a cathode or a 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.

[0165] The organic layer may sequentially 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) on the first electrode (110). At this time, the remaining layers, excluding the light-emitting layer (140), may not be formed. It may further include a hole blocking layer, an electron blocking layer, a light-emitting auxiliary layer (220), a buffer layer (210), etc., and the electron transport layer (150), etc., may serve as a hole blocking layer. (See FIG. 2)

[0166] Additionally, an organic electric device according to one embodiment of the present invention may further include a protective layer or a light efficiency improvement layer (180). Such a light efficiency improvement layer may be formed on the surface of the first electrode that does not come into contact with the organic layer or on the surface of the second electrode that does not come into contact with the organic layer. A compound according to one embodiment of the present invention applied to the organic layer may be used as a host or dopant of a hole injection layer (120), a hole transport layer (130), a light-emitting auxiliary layer (220), an electron transport auxiliary layer, an electron transport layer (150), an electron injection layer (160), a light-emitting layer (140), or as a material for the light efficiency improvement layer. Preferably, for example, a compound according to Formula 1 of the present invention may be used as a material for a light-emitting auxiliary layer or a hole transport layer.

[0167] The organic layer may include two or more stacks comprising a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on the anode, and may further include a charge generation layer formed between the two or more stacks. (See FIG. 3)

[0168] Meanwhile, even with the same core, the band gap, electrical properties, and interfacial properties can vary depending on which substituent is attached at which location; therefore, the selection of the core and the combination of sub-substituents attached to it are also very important. In particular, long lifespan and high efficiency can be achieved simultaneously when the energy levels and T1 values ​​between each organic layer, as well as the intrinsic properties of the material (mobility, interfacial properties, etc.), form an optimal combination.

[0169] An organic electroluminescent device according to one embodiment of the present invention can be manufactured using a physical vapor deposition (PVD) method. For example, it can be manufactured by forming an anode 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) thereon, and then depositing a material that can be used as a cathode thereon.

[0170] In addition, the present invention provides an organic electric device characterized in that the organic layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, and a roll-to-roll process, and the organic layer comprises the compound as an electron transport material.

[0171] As another specific example, the present invention provides an organic electric device characterized by using a homogeneous or heterogeneous compound of the compound represented by Chemical Formula 1 mixed in the organic layer.

[0172] In addition, the present invention provides a light-emitting auxiliary layer composition comprising a compound represented by the above chemical formula 1, and an organic electric device comprising the above light-emitting auxiliary layer.

[0173] In addition, the present invention provides a hole transport layer composition comprising a compound represented by the above chemical formula 1, and an organic electric device comprising the hole transport layer.

[0174] In addition, the present invention provides an electronic device comprising: a display device including the above-described organic electric element; and a control unit for driving the display device.

[0175] In another aspect, the present invention provides an electronic device characterized in that the organic electrical device comprises at least one of an organic electroluminescent device, an organic solar cell, an organic photosensitive material, an organic transistor, and a monochromatic or white lighting 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, PDAs, electronic dictionaries, PMPs, remote controls, navigation systems, game consoles, various TVs, and various computers.

[0177] In the following, examples of synthesis of the compound represented by Chemical Formula 1 of the present invention and examples of manufacturing of the organic electric device of the present invention will be described in detail, but the present invention is not limited to the following examples.

[0179] [ 합성예 ]

[0180] The compound represented by Formula 1 according to the present invention (Final product) may be prepared by reacting as shown in Reaction Scheme 1 below, but is not limited thereto. (Hal 1 is Br, I, or Cl.)

[0181] <Reaction Equation 1>

[0182]

[0184] I. Sub 1의 합성

[0185] Sub 1 of the above Reaction Scheme 1 can be synthesized by the reaction pathway of the following Reaction Scheme 2, but is not limited thereto. (Hal1 and Hal 2 is Br, I, or Cl.)

[0186] <Reaction Equation 2>

[0187]

[0188] 1. Sub1 -1의 합성예

[0189]

[0190] Sub1a-1 (5.4 g, 23.2 mmol) was placed in a round-bottom flask and dissolved in THF (81 mL) and water (27 mL). Then, Sub1b-1 (6.9 g, 25.3 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), and NaOH (42.5 g, 46.5 mmol) were added, and the mixture was stirred at 75°C. After the reaction was complete, the mixture was extracted with CH2Cl2 and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 5.3 g of product (yield: 60%).

[0192] 2. Sub1 -33의 합성예

[0193]

[0194] Sub1a-2 (7.0 g, 30.1 mmol) was placed in a round-bottom flask and dissolved in THF (105 mL) and water (35 mL), after which Sub1b-2 (13.0 g, 32.8 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and NaOH (55.2 g, 60.2 mmol) were added, and 9.4 g of product (yield: 62%) was obtained using the above Sub 1-1 synthesis method.

[0196] 3. Sub1 -59의 합성예

[0197]

[0198] Sub1a-3 (6.3 g, 18.6 mmol) was placed in a round-bottom flask and dissolved in THF (96 mL) and water (32 mL), then Sub1b-3 (8.1 g, 20.3 mmol), Pd(PPh3)4 (0.6 g, 0.6 mmol), and NaOH (34.1 g, 37.2 mmol) were added, and 6.7 g of product (yield: 59%) was obtained using the above Sub 1-1 synthesis method.

[0200] 4. Sub1 -74의 합성예

[0201]

[0202] 1) Synthesis of Sub 1b-4

[0203] Mg (1.2 g, 47.9 mmol) was placed in a round-bottom flask and heated sufficiently. Then, under a nitrogen stream, the starting material Sub1b'-1 (14.2 g, 39.9 mmol) was dissolved in THF (90 mL) and slowly added, followed by stirring at 85°C for 2 hours. In another round-bottom flask, Sub1b'-1 (10.5 g, 39.9 mmol) was dissolved in THF (150 mL), the previously prepared solution was slowly added at 0°C, and the mixture was stirred at room temperature for 4 hours. Once the reaction was complete, the reaction was terminated with 2M HCl, extracted with CH2Cl2 and water, dried and concentrated with MgSO4, and the resulting compound was recrystallized using a silicagel column to obtain 12.9 g of product (yield: 53%).

[0205] 2) Synthesis of Sub 1-74

[0206] Sub1a-4 (6.8 g, 24.1 mmol) was placed in a round-bottom flask and dissolved in THF (100 mL) and water (30 mL), then Sub1b-4 (11.6 g, 26.2 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), and NaOH (44.1 g, 48.1 mmol) were added, and 8.5 g of product (yield: 55%) was obtained using the above Sub 1-1 synthesis method.

[0208] Meanwhile, the compounds belonging to Sub 1 may be the following compounds, but are not limited thereto, and Table 1 below shows the FD-MS (Field Desorption-Mass Spectrometry) values ​​of the compounds belonging to Sub 1.

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0226] 화합물 FD-MS 화합물 FD-MS Sub1-1 m / z=380.13(C 27 H 21 Cl=380.92) Sub1-2 m / z=380.13(C 27 H 21 Cl=380.92) Sub1-3 m / z=380.13(C 27 H 21 Cl=380.92) Sub1-4 m / z=380.13(C 27 H 21 Cl=380.92) Sub1-5 m / z=380.13(C 27 H 21 Cl=380.92) Sub1-6 m / z=470.14(C 33 H 23 ClO=471.00) Sub1-7 m / z=430.15(C 31 H 23 Cl=430.98) Sub1-8 m / z=496.20(C 36 H 29 Cl=497.08) Sub1-9 m / z=380.13(C 27 H 21 Cl=380.92) Sub1-10 m / z=430.15(C 31 H 23 Cl=430.98) Sub1-11 m / z=456.16(C 33 H 25 Cl=457.01) Sub1-12 m / z=496.20(C 36 H 29 Cl=497.08) Sub1-13 m / z=380.13(C 27 H 21 Cl=380.92) Sub1-14 m / z=380.13(C 27 H 21 Cl=380.92) Sub1-15 m / z=430.15(C 31 H 23 Cl=430.98) Sub1-16 m / z=380.13(C 27 H 21 Cl=380.92) Sub1-17 m / z=380.13(C 27 H 21 Cl=380.92) Sub1-18 m / z=380.13(C 27 H 21 Cl=380.92) Sub1-19 m / z=380.13(C 27 H 21 Cl=380.92) Sub1-20 m / z=380.13(C 27 H 21 Cl=380.92) Sub1-21 m / z=430.15(C 31 H 23 Cl=430.98) Sub1-22 m / z=380.13(C 27 H 21 Cl=380.92) Sub1-23 m / z=380.13(C 27 H 21 Cl=380.92) Sub1-24 m / z=482.18(C 35 H 27 Cl=483.05) Sub1-25 m / z=456.16(C 33 H 25 Cl=457.01) Sub1-26 m / z=456.16(C 33 H 25 Cl=457.01) Sub1-27 m / z=430.15(C 31 H 23 Cl=430.98) Sub1-28 m / z=430.15(C 31 H 23 Cl=430.98) Sub1-29 m / z=430.15(C 31 H 23 Cl=430.98) Sub1-30 m / z=480.16(C 35 H 25 Cl=481.04) Sub1-31 m / z=532.20(C 39 H 29 Cl=533.11) Sub1-32 m / z=486.12(C 33 H 23 ClS=487.06) Sub1-33 m / z=504.16(C 37 H 25 Cl=505.06) Sub1-34 m / z=504.16(C 37 H 25 Cl=505.06) Sub1-35 m / z=504.16(C 37 H 25 Cl=505.06) Sub1-36 m / z=554.18(C 41 H 27 Cl=555.12) Sub1-37 m / z=554.18(C 41 H 27 Cl=555.12) Sub1-38 m / z=580.20(C 43 H 29 Cl=581.16) Sub1-39 m / z=504.16(C 37 H 25 Cl=505.06) Sub1-40 m / z=620.23(C 46 H 33 Cl=621.22) Sub1-41 m / z=504.16(C 37 H 25 Cl=505.06) Sub1-42 m / z=504.16(C 37 H 25 Cl=505.06) Sub1-43 m / z=554.18(C 41 H 27 Cl=555.12) Sub1-44 m / z=610.15(C 43 H 27 ClS=611.20) Sub1-45 m / z=562.24(C 41 H 35 Cl=563.18) Sub1-46 m / z=594.18(C 43 H 27 ClO=595.14) Sub1-47 m / z=580.20(C 43 H 29 Cl=581.16) Sub1-48 m / z=504.16(C 37 H 25 Cl=505.06) Sub1-49 m / z=580.20(C 43 H 29 Cl=581.16) Sub1-50 m / z=504.16(C 37 H 25 Cl=505.06) Sub1-51 m / z=554.18(C 41 H 27 Cl=555.12) Sub1-52 m / z=604.20(C 45 H 29 Cl=605.18) Sub1-53 m / z=554.18(C 41 H 27 Cl=555.12) Sub1-54 m / z=604.20(C 45 H 29 Cl=605.18) Sub1-55 m / z=620.23(C 46 H 33 Cl=621.22) Sub1-56 m / z=604.20(C 45 H 29 Cl=605.18) Sub1-57 m / z=505.16(C 36 H 24 ClN=506.05) Sub1-58 m / z=544.16(C 39 H 25 ClO=545.08) Sub1-59 m / z=610.15(C 43 H 27 ClS=611.20) Sub1-60 m / z=530.18(C 39 H 27 Cl=531.10) Sub1-61 m / z=554.18(C 41 H 27 Cl=555.12) Sub1-62 m / z=680.23(C 51 H 33 Cl=681.28) Sub1-63 m / z=581.19(C 42 H 28 ClN=582.14) Sub1-64 m / z=732.26(C 55 H 37 Cl=733.35) Sub1-65 m / z=580.20(C 43 H 29 Cl=581.16) Sub1-66 m / z=554.18(C 41 H 27 Cl=555.12) Sub1-67 m / z=554.18(C 41 H 27 Cl=555.12) Sub1-68 m / z=554.18(C 41 H 27 Cl=555.12) Sub1-69 m / z=504.16(C 37 H 25 Cl=505.06) Sub1-70 m / z=504.16(C 37 H 25 Cl=505.06) Sub1-71 m / z=594.18(C 43 H 27 ClO=595.14) Sub1-72 m / z=610.15(C 43 H 27 ClS=611.20) Sub1-73 m / z=594.18(C 43 H 27 ClO=595.14) Sub1-74 m / z=644.19(C 47 H 29 ClO=645.20) Sub1-75 m / z=670.24(C 50 H 35 Cl=671.28) Sub1-76 m / z=669.22(C 49 H 32 ClN=670.25) Sub1-77 m / z=560.14(C 39 H 25 ClS=561.14) Sub1-78 m / z=544.16(C 39 H 25 ClO=545.08) Sub1-79 m / z=496.20(C 36 H 29 Cl=497.08) Sub1-80 m / z=506.18(C 37 H 27 Cl=507.07) Sub1-81 m / z=660.17(C 47 H 29 ClS=661.26) Sub1-82 m / z=594.18(C 43 H 27 ClO=595.14) Sub1-83 m / z=594.18(C 43 H 27 ClO=595.14) Sub1-84 m / z=700.16(C 49 H 29 ClOS=701.28) Sub1-85 m / z=630.21(C 47 H 31 Cl=631.22) Sub1-86 m / z=580.20(C 43 H 29 Cl=581.16) Sub1-87 m / z=680.23(C 51 H 33 Cl=681.28) Sub1-88 m / z=696.26(C 52 H 37 Cl=697.32) Sub1-89 m / z=686.18(C 49 H 31 ClS=687.30) Sub1-90 m / z=630.21(C 47 H 31 Cl=631.22) Sub1-91 m / z=680.23(C 51 H 33 Cl=681.28) Sub1-92 m / z=656.23(C 49 H 33 Cl=657.25) Sub1-93 m / z=670.21(C 49 H 31 ClO=671.24) Sub1-94 m / z=736.20(C 53 H 33 ClS=737.36) Sub1-95 m / z=604.20(C 45 H 29 Cl=605.18) Sub1-96 m / z=572.17(C 41 H 26 ClF=573.11)

[0228] II. Sub 2의 합성

[0229] Sub 2 of the above reaction scheme 1 can be synthesized by the reaction pathway of the following reaction scheme 3, but is not limited thereto.

[0230] <Reaction Equation 3>

[0231]

[0232] Examples of the synthesis of specific compounds belonging to Sub 2 are as follows.

[0234] 1. Sub 2-1 합성예

[0235]

[0236] In a round-bottom flask, Sub2c-1 (10.0 g, 42.9 mmol), Sub2d-1 (4.0 g, 42.9 mmol), Pd2(dba)3(1.2 g, 1.3 mmol), P( t -Bu)3(50wt% Sol.) (1.04 mL, 2.6 mmol), NaO t -Bu (12.4 g, 128.7 mmol) and Toluene (250 mL) were added and stirred at 80°C. After the reaction was complete, the mixture was extracted with CH2Cl2 and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 8.7 g of product (yield: 83%).

[0238] 2. Sub 2-24 합성예

[0239]

[0240] In a round-bottom flask, Sub2c-2 (8.5 g, 32.3 mmol), Sub2d-2 (3.6 g, 32.3 mmol), Pd2(dba)3(0.9 g, 0.97 mmol), P( t-Bu)3(50wt% Sol.) (0.8 mL, 1.94 mmol), NaO t -Bu (9.3 g, 96.9 mmol) and Toluene (200 mL) were added, and 7.49 g of product (yield: 79%) was obtained using the above Sub 2-1 synthesis method.

[0242] Meanwhile, compounds belonging to Sub 2 may be the following compounds, but are not limited thereto, and Table 2 below shows the FD-MS values ​​of compounds belonging to Sub 2.

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0255] 화합물 FD-MS 화합물 FD-MS Sub 2-1 m / z=245.12(C 18 H 15 N=245.33) Sub 2-2 m / z=295.14(C 22 H 17 N=295.39) Sub 2-3 m / z=295.14(C 22 H 17 N=295.39) Sub 2-4 m / z=295.14(C 22 H 17 N=295.39) Sub 2-5 m / z=345.15(C 26 H 19 N=345.45) Sub 2-6 m / z=245.12(C 18 H 15 N=245.33) Sub 2-7 m / z=295.14(C 22 H 17 N=295.39) Sub 2-8 m / z=285.15(C 21 H 19 N=285.39) Sub 2-9 m / z=271.14(C 20 H 17 N=271.36) Sub 2-10 m / z=335.17(C 25 H 21 N=335.45) Sub 2-11 m / z=335.17(C 25 H 21 N=335.45) Sub 2-12 m / z=295.14(C 22 H 17 N=295.39) Sub 2-13 m / z=263.11(C 18 H 14 FN=263.32) Sub 2-14 m / z=285.12(C 20 H 15 NO=285.35) Sub 2-15 m / z=311.17(C 23 H 21 N=311.43) Sub 2-16 m / z=335.13(C 24 H 17 NO=335.41) Sub 2-17 m / z=275.08(C 18 H 13 NS=275.37) Sub 2-18 m / z=334.15(C 24 H 18 N2=334.42) Sub 2-19 m / z=187.08(C 12 H 10 FN=187.22) Sub 2-20 m / z=409.18(C 31 H 23 N=409.53) Sub 2-21 m / z=485.21(C 37 H 27 N=485.63) Sub 2-22 m / z=245.12(C 18 H 15 N=245.33) Sub 2-23 m / z=395.17(C 30 H 21 N=395.51) Sub 2-24 m / z=293.07(C 18 H 12 FNS=293.36) Sub 2-25 m / z=321.15(C 24 H 19 N=321.42) Sub 2-26 m / z=271.14(C 20 H 17 N=271.36) Sub 2-27 m / z=313.13(C 22 H 16 FN=313.38) Sub 2-28 m / z=295.14(C 22 H 17 N=295.39) Sub 2-29 m / z=309.12(C 22 H 15 NO=309.37) Sub 2-30 m / z=335.17(C 25 H 21 N=335.45) Sub 2-31 m / z=351.11(C 24 H 17 NS=351.47) Sub 2-32 m / z=345.15(C 26 H 19 N=345.45) Sub 2-33 m / z=285.15(C 21 H 19 N=285.39) Sub 2-34 m / z=331.23(C 24 H 29 N=331.50) Sub 2-35 m / z=345.15(C 26 H 19 N=345.45) Sub 2-36 m / z=369.15(C 28 H 19 N=369.47) Sub 2-37 m / z=377.18(C 27 H 23 NO=377.49) Sub 2-38 m / z=224.14(C 16 H8D5N=224.32) Sub 2-39 m / z=335.17(C 25 H 21 N=335.45) Sub 2-40 m / z=374.19(C 28 H 18 D3N=374.50) Sub 2-41 m / z=351.20(C 26 H 25 N=351.49) Sub 2-42 m / z=423.16(C 31 H 21 NO=423.52) Sub 2-43 m / z=321.15(C 24 H 19 N=321.42) Sub 2-44 m / z=325.09(C 22 H 15 NS=325.43) Sub 2-45 m / z=371.17(C 28 H 21 N=371.48) Sub 2-46 m / z=303.20(C 22 H 25 N=303.45) Sub 2-47 m / z=353.12(C 24 H 16 FNO=353.40) Sub 2-48 m / z=347.17(C 26 H 21 N=347.46) Sub 2-49 m / z=225.06(C 14 H 11 NS=225.31) Sub 2-50 m / z=407.17(C 31 H 21 N=407.52) Sub 2-51 m / z=325.09(C 22 H 15 NS=325.43) Sub 2-52 m / z=412.19(C 30 H 24 N2=412.54) Sub 2-53 m / z=291.07(C 18 H 13 NOS=291.37) Sub 2-54 m / z=411.20(C 31 H 25 N=411.55) Sub 2-55 m / z=351.11(C 24 H 17 NS=351.47) Sub 2-56 m / z=361.18(C 27 H 23 N=361.49) Sub 2-57 m / z=169.09(C 12 H 11 N=169.23) Sub 2-58 m / z=174.12(C 12 H6D5N=174.26) Sub 2-59 m / z=453.16(C 32 H 23 NS=453.6) Sub 2-60 m / z=360.16(C 26 H 20 N2=360.46) Sub 2-61 m / z=423.20(C 32 H 25 N=423.56) Sub 2-62 m / z=321.15(C 24 H 19 N=321.42) Sub 2-63 m / z=363.16(C 26 H 21 NO=363.46) Sub 2-64 m / z=334.15(C 24 H 18 N2=334.42) Sub 2-65 m / z=439.14(C 31 H 21 NS=439.58) Sub 2-66 m / z=371.17(C 28 H 21 N=371.48) Sub 2-67 m / z=287.17(C 21 H 21 N=287.41) Sub 2-68 m / z=423.16(C 31 H 21 NO=423.52) Sub 2-69 m / z=339.11(C 23 H 17 NS=339.46) Sub 2-70 m / z=371.17(C 28 H 21 N=371.48) Sub 2-71 m / z=313.11(C 19 H 14 F3N=313.32) Sub 2-72 m / z=281.10(C 18 H 13 F2N=281.31) Sub 2-73 m / z=381.11(C 23 H 15 F4N=381.37) Sub 2-74 m / z=347.17(C 26 H 21 N=347.46)

[0257] III. Synthesis of the Final Compound

[0258] 1. P-1 Synthetic example

[0259]

[0260] After dissolving Sub1-1 (11.4 g, 29.9 mmol) in Toluene (250 mL) in a round-bottom flask, Sub2-1 (7.3 g, 29.9 mmol), Pd2(dba)3 (0.8 g, 0.9 mmol), P( t -Bu)3(50wt% Sol.) (0.7 mL, 1.8 mmol), NaO t -Bu (8.6 g, 89.8 mmol) was added and stirred at 80°C. After the reaction was complete, the mixture was extracted with CH2Cl2 and water, the organic layer was dried with MgSO4 and concentrated, and the resulting compound was purified by silicagel column and sublimation to obtain 14.3 g of product (yield: 81%).

[0262] 2. P-47 Synthetic example

[0263]

[0264] Sub 1-33 (13.4 g, 26.5 mmol) and Sub 2-2 (7.8 g, 26.5 mmol), Pd2(dba)3(0.7 g, 0.8 mmol), NaO t -Bu (7.7 g, 79.6 mmol), anhydrous toluene (300 mL), P( t 15.8 g of product (yield: 78%) was obtained using the synthesis method of P-1 above with -Bu)3 (50 wt% Sol.) (0.6 mL, 1.6 mmol).

[0266] 3. P-51 Synthetic example

[0267]

[0268] Sub 1-83 (9.7 g, 16.3 mmol) and Sub 2-6 (4.0 g, 16.3 mmol), Pd2(dba)3(0.5 g, 0.5 mmol), NaO t -Bu (4.7 g, 48.9 mmol), anhydrous toluene (200 mL), P( t10.8 g of product (yield: 83%) was obtained using the synthesis method of P-1 above with -Bu)3 (50 wt% Sol.) (0.4 mL, 1.0 mmol).

[0270] Meanwhile, the FD-MS values ​​of compounds P-1 to P-123 of the present invention prepared according to the synthesis example above are as shown in Table 3 below.

[0271] compound FD-MS compound FD-MS P-1 m / z=589.28(C 45 H 35 N=589.78) P-2 m / z=639.29(C 49 H 37 N=639.84) P-3 m / z=639.29(C 49 H 37 N=639.84) P-4 m / z=639.29(C 49 H 37 N=639.84) P-5 m / z=689.31(C 53 H 39 N=689.90) P-6 m / z=589.28(C 45 H 35 N=589.78) P-7 m / z=639.29(C 49 H 37 N=639.84) P-8 m / z=629.31(C 48 H 39 N=629.85) P-9 m / z=615.29(C 47 H 37 N=615.82) P-10 m / z=679.32(C 52 H 41 N=679.91) P-11 m / z=679.32(C 52 H 41 N=679.91) P-12 m / z=639.29(C 49 H 37 N=639.84) P-13 m / z=679.29(C 51 H 37 NO=679.86) P-14 m / z=629.27(C 47 H 35 NO=629.80) P-15 m / z=655.32(C 50 H 41 N=655.89) P-16 m / z=639.29(C 49 H 37 N=639.84) P-17 m / z=755.36(C 58 H 45 N=756.01) P-18 m / z=679.29(C 51 H 37 NO=679.86) P-19 m / z=619.23(C 45 H 33 NS=619.83) P-20 m / z=639.29(C 49 H 37 N=639.84) P-21 m / z=683.30(C 51 H 38 FN=683.87) P-22 m / z=647.30(C 48 H 38 FN=647.84) P-23 m / z=678.30(C 51 H 38 N2=678.88) P-24 m / z=637.22(C 45 H 32 FNS=637.82) P-25 m / z=715.32(C 55 H 41 N=715.94) P-26 m / z=753.34(C 58 H 43 N=753.99) P-27 m / z=829.37(C 64 H 47 N=830.09) P-28 m / z=745.28(C 55 H 39 NS=745.98) P-29 m / z=589.28(C 45 H 35 N=589.78) P-30 m / z=739.32(C 57 H 41 N=739.96) P-31 m / z=665.31(C 51 H 39 N=665.88) P-32 m / z=639.29(C 49 H 37 N=639.84) P-33 m / z=653.27(C 49 H 35 NO=653.83) P-34 m / z=695.26(C 51 H 37 NS=695.92) P-35 m / z=675.39(C 51 H 49 N=675.96) P-36 m / z=691.32(C 53 H 41 N=691.92) P-37 m / z=733.31(C 55 H 40 FN=733.93) P-38 m / z=791.36(C 61 H 45 N=792.04) P-39 m / z=721.33(C 54 H 43 NO=721.94) P-40 m / z=644.32(C 49 H 32 D5N=644.87) P-41 m / z=639.29(C 49 H 37 N=639.84) P-42 m / z=689.31(C 53 H 39 N=689.90) P-43 m / z=729.34(C 56 H 43 N=729.97) P-44 m / z=779.36(C 60 H 45 N=780.03) P-45 m / z=718.34(C 55 H 38 D3N=718.96) P-46 m / z=713.31(C 55 H 39 N=713.92) P-47 m / z=763.32(C 59 H 41 N=763.98) P-48 m / z=763.32(C 59 H 41 N=763.98) P-49 m / z=763.32(C 59 H 41 N=763.98) P-50 m / z=813.34(C 63 H 43 N=814.04) P-51 m / z=803.32(C 61 H 41 NO=804.01) P-52 m / z=763.32(C 59 H 41 N=763.98) P-53 m / z=753.34(C 58 H 43 N=753.99) P-54 m / z=819.39(C 63 H 49 N=820.09) P-55 m / z=815.36(C 63 H 45 N=816.06) P-56 m / z=763.32(C 59 H 41 N=763.98) P-57 m / z=813.34(C 63 H 43 N=814.04) P-58 m / z=839.36(C 65 H 45 N=840.08) P-59 m / z=813.34(C 63 H 43 N=814.04) P-60 m / z=837.34(C 65 H 43 N=838.07) P-61 m / z=693.25(C 51 H 35 NS=693.91) P-62 m / z=955.42(C 74 H 53 N=956.25) P-63 m / z=821.31(C 61 H 40 FNO=822.00) P-64 m / z=789.34(C 61 H 43 N=790.02) P-65 m / z=763.32(C 59 H 41 N=763.98) P-66 m / z=831.35(C 63 H 45 NO=832.06) P-67 m / z=891.35(C 68 H 45 NO=892.11) P-68 m / z=789.34(C 61 H 43 N=790.02) P-69 m / z=899.27(C 65 H 41 NS2=900.17) P-70 m / z=891.35(C 68 H 45 NO=892.11) P-71 m / z=771.39(C 59 H 49 N=772.05) P-72 m / z=821.40(C 63 H 51 N=822.11) P-73 m / z=807.30(C 60 H 41 NS=808.06) P-74 m / z=803.32(C 61 H 41 NO=804.01) P-75 m / z=915.39(C 71 H 49 N=916.18) P-76 m / z=875.36(C 68 H 45 N=876.12) P-77 m / z=878.37(C 67 H 46 N2=879.12) P-78 m / z=793.28(C 59 H 39 NS=794.03) P-79 m / z=880.38(C 67 H 48 N2=881.14) P-80 m / z=739.32(C 57 H 41 N=739.96) P-81 m / z=763.32(C 59 H 41 N=763.98) P-82 m / z=863.36(C 67 H 45 N=864.10) P-83 m / z=809.28(C 59 H 39 NOS=810.03) P-84 m / z=1007.36(C 76 H 49 NS=1008.30) P-85 m / z=880.38(C 67 H 48 N2=881.14) P-86 m / z=869.40(C 67 H 51 N=870.15) P-87 m / z=819.30(C 61 H 41 NS=820.07) P-88 m / z=929.40(C 72 H 51 N=930.21) P-89 m / z=677.27(C 51 H 35 NO=677.85) P-90 m / z=748.30(C 55 H 32 D5NS=749.00) P-91 m / z=763.32(C 59 H 41 N=763.98) P-92 m / z=813.34(C 63 H 43 N=814.04) P-93 m / z=830.37(C 63 H 46 N2=831.08) P-94 m / z=915.39(C 71 H 49 N=916.18) P-95 m / z=941.40(C 73 H 51 N=942.22) P-96 m / z=895.33(C 67 H 45 NS=896.16) P-97 m / z=813.34(C 63 H 43 N=814.04) P-98 m / z=813.34(C 63 H 43 N=814.04) P-99 m / z=828.35(C 63 H 44 N2=829.06) P-100 m / z=891.39(C 69 H 49 N=892.16) P-101 m / z=803.32(C 61 H 41 NO=804.01) P-102 m / z=869.31(C 65 H 43 NS=870.13) P-103 m / z=839.30(C 61 H 39 F2NO=839.99) P-104 m / z=989.33(C 70 H 43 F4NO=990.11) P-105 m / z=921.43(C 71 H 55 N=922.23) P-106 m / z=928.38(C 71 H 48 N2=929.18) P-107 m / z=845.31(C 63 H 43 NS=846.10) P-108 m / z=803.32(C 61 H 41 NO=804.01) P-109 m / z=869.31(C 65 H 43 NS=870.13) P-110 m / z=853.33(C 65 H 43 NO=854.07) P-111 m / z=839.36(C 65 H 45 N=840.08) P-112 m / z=789.34(C 61 H 43 N=790.02) P-113 m / z=939.39(C 73 H 49 N=940.20) P-114 m / z=955.42(C 74 H 53 N=956.25) P-115 m / z=950.37(C 71 H 42 D5NS=951.25) P-116 m / z=839.36(C 65 H 45 N=840.08) P-117 m / z=813.34(C 63 H 43 N=814.04) P-118 m / z=915.39(C 71 H 49 N=916.18) P-119 m / z=929.37(C 71 H 47 NO=930.16) P-120 m / z=995.36(C 75 H 49 NS=996.28) P-121 m / z=813.34(C 63 H 43 N=814.04) P-122 m / z=831.33(C 63 H 42 FN=832.03) P-123 m / z=781.30(C 56 H 38 F3N=781.92)

[0273] Manufacturing evaluation of organic electrical devices

[0274] [ Examples 1] Blue organic electroluminescent device ( light-emitting auxiliary layer )

[0275] A hole injection layer was formed by vacuum depositing 2-TNATA to a thickness of 60 nm on an ITO layer (anode) formed on a glass substrate, and then a hole transport layer was formed by vacuum depositing NPB to a thickness of 60 nm on the hole injection layer. Subsequently, a light-emitting auxiliary layer was formed by vacuum depositing compound P-1 of the present invention to a thickness of 20 nm on the hole transport layer, and then a light-emitting layer with a thickness of 30 nm was formed on the light-emitting auxiliary layer using 9,10-di(naphthalen-2-yl)anthracene as a host and BD-052X (manufactured by Idemitsu Kosan) as a dopant in a weight ratio of 96:4. Next, a hole blocking layer was formed by vacuum depositing BAlq to a thickness of 10 nm on the light-emitting layer, and an electron transport layer was formed by vacuum depositing tris-(8-hydroxyquinoline)aluminum (hereinafter abbreviated as "Alq3") to a thickness of 40 nm on the hole blocking layer. Subsequently, an electron injection layer was formed by depositing LiF to a thickness of 0.2 nm, and then a cathode was formed by depositing Al to a thickness of 150 nm, thereby manufacturing an organic electroluminescent device.

[0277] [ Examples 2] to [ Examples 15] Blue organic electroluminescent device ( light-emitting auxiliary layer )

[0278] 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 4 below was used instead of the compound P-1 of the present invention as the light-emitting auxiliary layer material.

[0280] [ Comparative example 1] and [ Comparative example 2]

[0281] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that Comparative Compound 1 or Comparative Compound 2 listed in Table 4 below was used instead of Compound P-1 of the present invention as the light-emitting auxiliary layer material.

[0282] <Comparative Compound 1> <Comparative Compound 2>

[0283]

[0284] Electroluminescence (EL) characteristics were measured using a PR-650 from Photoresearch by applying a forward-bias DC voltage to the organic electroluminescent devices prepared according to Examples 1 to 15 and Comparative Examples 1 and 2 of the present invention, and 500 cd / m² 2 The T95 lifespan was measured at standard brightness using a lifespan measuring device manufactured by MaxScience, and the measurement results are as shown in Table 4 below.

[0285] compound Voltage(V) CurrentDensity(mA / cm 2 ) Brightness(cd / m 2 ) Efficiency(cd / A) LifetimeT(95) Comparative example (1) Comparative Compound 1 5.6 12.5 500.0 4.0 73.5 Comparative example (2) Comparative Compound 2 5.2 10.9 500.0 4.6 86.1 Example (1) P-1 4.7 8.7 500.0 5.7 115.8 Example (2) P-3 4.7 8.8 500.0 5.7 113.9 Example (3) P-13 4.6 8.6 500.0 5.8 116.2 Example (4) P-19 4.6 8.4 500.0 6.0 117.6 Example (5) P-23 4.8 8.9 500.0 5.6 115.2 Example (6) P-47 4.5 7.9 500.0 6.3 119.8 Example (7) P-51 4.7 8.1 500.0 6.2 118.3 Example (8) P-55 4.6 8.2 500.0 6.1 118.9 Example (9) P-57 4.5 8.1 500.0 6.2 115.7 Example (10) P-61 4.8 8.8 500.0 5.7 113.4 Example (11) P-62 4.7 8.7 500.0 5.7 116.0 Example (12) P-65 4.6 8.5 500.0 5.9 116.3 Example (13) P-76 4.7 8.6 500.0 5.8 117.6 Example (14) P-91 4.6 8.3 500.0 6.0 116.3 Example (15) P-103 4.9 8.6 500.0 5.8 113.4 Example (16) P-112 4.8 9.3 500.0 5.4 111.9

[0286] As can be seen from the results of Table 4 above, when a blue organic electroluminescent device is fabricated using the material for the organic electroluminescent device of the present invention as a light-emitting auxiliary layer material, it can be seen that not only can the driving voltage of the organic electroluminescent device be lowered compared to when comparative compound 1 and comparative compound 2, which have a basic framework similar to the compound of the present invention, are used, but the luminous efficiency and lifespan can also be improved.

[0287] To explain in detail, the comparative compound and the compound of the present invention are identical in that an amine substituent is bonded to diphenylfluorene, but the device results of comparative compound 2, in which a linker exists between diphenylfluorene and an amine group, are improved compared to comparative compound 1, in which an amine group is directly bonded to diphenylfluorene. Additionally, it can be confirmed that the device results of the compound of the present invention, which is similar to comparative compound 2 in that a linker exists between diphenylfluorene and an amine group but a secondary substituent is further substituent on the linker, are improved overall.

[0288] These results can be explained by the HOMO values ​​of Comparative Compound 1, Comparative Compound 2, and the compound of the present invention. Referring to Table 5 below, it can be confirmed that the HOMO value of Comparative Compound P-47 of the present invention, in which a linker exists between the diphenylfluorene and the amine group and a secondary substituent is further substituted on the linker, is the highest.

[0289] Comparative Compound 1 Comparative Compound 2 P-47 HOMO (eV) -5.023 -4.997 -4.949

[0290] In other words, due to this difference, the charge balance is improved because the hole transport layer to the light-emitting layer is faster and smoother than that of the comparative compound. Consequently, the interfacial luminescence between the light-emitting auxiliary layer and the host is reduced, and since light emission mainly occurs within the host, it is determined that this affects the overall performance of the device.

[0291] In particular, among the compounds of the present invention, it can be confirmed that the device results of a compound structure in which a linker is attached to the 4th position of the fluorene moiety core and an amine group is attached to the ortho position of the linker show a slight improvement in terms of driving voltage and efficiency.

[0292] In conclusion, it suggests that depending on the presence and location of the substituent, the physical properties of the compound, such as hole characteristics, photoelectric efficiency characteristics, energy levels (LUMO, HOMO levels, T1 levels), hole injection & mobility characteristics, and electron blocking characteristics, may differ, which can lead to completely different device results.

[0293] In the case of the light-emitting auxiliary layer, the relationship between the hole transport layer and the light-emitting layer (host) must be understood, so even if a similar core is used, it would be very difficult for a person skilled in the art to infer the characteristics exhibited by the light-emitting auxiliary layer using the compound of the present invention.

[0294] In addition, although the device characteristics described in the evaluation results of the aforementioned device fabrication involved applying the compound of the present invention to only one layer of the light-emitting auxiliary layer, the compound of the present invention may also be applicable when forming a hole transport layer or both the hole transport layer and the light-emitting auxiliary layer.

[0295] 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 within the scope of the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are intended to illustrate, not limit, the present invention, and the spirit and scope of the present invention are not limited by such embodiments. 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. Explanation of the symbols

[0297] 100, 200, 300 : Organic electrical device 110 : First electrode 120 : Hole injection layer 130 : Hole transport layer 140: Emitting layer 150: Electron transport layer 160: Electron injection layer 170: Second electrode 180: Light efficiency improvement layer 210: Buffer layer 220: Light-emitting auxiliary layer 320: First hole injection layer 330: 1st hole transport layer 340: 1st light-emitting layer 350: First electron transport layer 360: First charge generation layer 361 : Second charge generation layer 420 : Second hole injection layer 430: Second hole transport layer 440: Second light-emitting layer 450: Second electron transport layer CGL: Charge generation layer ST1: 1st Stack ST2: 2nd Stack

Claims

Claim 1 Compounds represented by any one of the following chemical formulas 1-1 to 1-4 <Chemical Formula 1-1> <Chemical Formula 1-2> <Chemical Formula 1-3> <Chemical Formula 1-4> {In the above chemical formulas 1-1 to 1-4, 1) Ar 1 and Ar 2 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 group of; and C1~C 60 Selected from the group consisting of the alkyl group of; and Ar 1 and Ar 2 ) cannot combine with each other to form a ring,2) Ar 3 is C6~C 60 aryl group; fluorenyl group; C2~C comprising at least one heteroatom among O, N, S, Si and P 60 The heterocyclic group of; and C1~C 60 Selected from the group consisting of alkyl groups; and Ar 4 is C6~C 60 A C2-C comprising an aryl group; a fluorenyl group; and at least one heteroatom among O, N, S, Si, and P. 60 Selected from a group consisting of heterocyclic rings,3) L 1 C6~C 60 arylene group; fluorenyllene group; and C2~C 60 Selected from a group consisting of heterocyclic rings,4) R 1 and R 2 Each is identical or different and independently hydrogen; deuterium; tritium; halogen; C1~C 50 alkyl group of; and C2~C 20 Selected from a group consisting of alkenes; and adjacent multiple R 1 Among themselves, or multiple Rs 2 They can combine with each other to form a ring,5) R 3 It contains hydrogen; deuterium; tritium; halogen; and C1~C 50 Selected from the group consisting of alkyl groups; 6) a is an integer from 0 to 4, b is an integer from 0 to 3, and c is an integer from 0 to 5, 7) where the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenyllene group, alkyl group and alkenyl group are each deuterium; halogen; C1~C 20 alkyl group of; C2~C 20 Alken Diary; C6~C 20 aryl group of; C6~C substituted with deuterium 20 aryl group; fluorene group; C2~C 20 heterocyclic; and C3~C 20 It may be further substituted with one or more substituents selected from the group consisting of a cycloalkyl group; provided, however, in the case of Formula 1-2, L 1 C6~C 10 arylene group of; or C2~C 30 The heterocyclic of; and, R 1 and R 2 Each cannot combine with others to form a ring. Claim 2 delete Claim 3 In claim 1, the compound is characterized by being represented by the following chemical formula 2 <Chemical Formula 2> {In the above chemical formula 2, 1) Ar 1 , Ar 2 , Ar 3 , Ar 4 , R 1 , R 2 , R 3 , a, b and c are the same as defined in Claim 1 above, and 2) R 4 is R of claim 1 above 1 Identical to the definition of and adjacent multiple R 4 They can combine with each other to form a ring,3) and d is an integer from 0 to 3. Claim 4 In claim 1, the compound is characterized by being represented by the following chemical formula 3 <Chemical Formula 3> {In the above chemical formula 3, 1) Ar 1 , Ar 2 , Ar 4 , R 1 , R 2 , R 3 , a, b and c are the same as defined in Claim 1 above, and 2) R 4 and d are the same as defined in claim 3 above, and 3) R 5 is R of claim 1 above 1 Identical to the definition of, and adjacent multiple R 5 They can combine with each other to form a ring,4) and e is an integer from 0 to 5. Claim 5 In claim 1, the compound is characterized by being represented by the following chemical formula 4 <Chemical Formula 4> {In the above chemical formula 4, 1) Ar 1 , Ar 2 , Ar 4 , R 1 , R 2 , R 3 , a, b and c are the same as defined in Claim 1 above, and 2) R 4 and d are the same as defined in claim 3 above, and 3) R 5 and e are the same as defined in claim 4 above. Claim 6 In claim 1, the compound is characterized by being represented by any one of the following chemical formulas 4-1 to 4-3 <Chemical Formula 4-1> <Chemical Formula 4-2> <Chemical Formula 4-3> {In the above chemical formulas 4-1 to 4-3, 1) Ar 1 , Ar 2 , Ar 4 , R 1 , R 2 , R 3 , a, b and c are the same as defined in Claim 1 above, and 2) R 4 and d are the same as defined in claim 3 above, and 3) R 5 and e are the same as defined in claim 4 above. Claim 7 A compound according to claim 1, characterized in that the compound is any one of the following compounds. Claim 8 An organic electric device comprising an anode, a cathode, and an organic layer formed between the anode and the cathode, wherein the organic layer comprises a single compound represented by any one of Chemical Formulas 1-1 to 1-4 according to claim 1, or two or more compounds. Claim 9 An organic electric device according to claim 8, wherein the organic layer comprises at least one of a hole injection layer, a hole transport layer, a light emission assist layer, a light emission layer, an electron transport assist layer, an electron transport layer, and an electron injection layer. Claim 10 An organic electric device according to claim 8, characterized in that the organic layer is a light-emitting auxiliary layer. Claim 11 An organic electric device according to claim 8, characterized in that the organic layer is a hole transport layer. Claim 12 In claim 8, an organic electric device further comprising a light efficiency improvement layer formed on at least one surface of the anode and cathode opposite to the organic layer. Claim 13 An organic electric device according to claim 8, characterized in that the organic layer is a light efficiency improvement layer. Claim 14 An organic electrical device according to claim 8, wherein 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 an anode. Claim 15 An organic electric device according to claim 14, wherein the organic layer further comprises a charge generating layer formed between the two or more stacks. Claim 16 An electronic device comprising: a display device including an organic electric element of claim 8; and a control unit for driving the display device. Claim 17 An electronic device according to claim 16, wherein the organic electrical device is at least one of an organic electroluminescent device (OLED), an organic solar cell, an organic photosensitive material (OPC), an organic transistor (organic TFT), and a device for monochromatic or white lighting.

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