Organic electrical element including compound for organic electrical element, and electronic device thereof

Abstract

The present invention provides an organic electric element in which at least one of compounds represented by Chemical Formula 1 and Chemical Formula 2 is included in a light-emitting auxiliary layer, and at least one of compounds represented by Chemical Formula 3 and Chemical Formula 4 is included in a light-emitting layer, and an electronic device including the organic electric element. The light-emitting auxiliary layer and the light-emitting layer include the compound according to the present invention, so that the driving voltage of the organic electric element can be reduced, and the light-emitting efficiency and lifetime of the organic electric element can be improved.

Description

[0001] Description of the case

[0002] The present invention is a divisional application of Chinese Patent Application No. 202280074876.3, claiming priority and the benefits of Korean Patent Application No. KR1020210155740, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The present invention relates to an organic electric element including a compound for an organic electric element, and an electronic device thereof. Background Art

[0004] In organic electrical elements, materials used as organic layers can be divided into luminescent materials and charge transport materials according to their functions, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials. In addition, transport luminescent materials can be divided into high molecular weight and low molecular weight types according to their molecular weight, and can be divided into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons according to their luminescent mechanism. In addition, luminescent materials can be divided into blue, green, and red luminescent materials and yellow and vermilion luminescent materials for better natural colors according to their luminescent colors.

[0005] When a substance is used as a light-emitting material, there are problems that the maximum emission wavelength moves to a longer wavelength due to the interaction between molecules, and the efficiency of the element is reduced due to the reduction of pure chromaticity or the effect of luminescence attenuation. Therefore, in order to increase the luminous efficiency by increasing the pure chromaticity and transferring energy, a matrix / doping type can be used as a light-emitting material. The principle is that if a small amount of dopant with a smaller energy band interval is mixed into the light-emitting layer compared to the main body forming the light-emitting layer, the excitons generated in the light-emitting layer are transported to the dopant, so that light with high efficiency is emitted. At this time, since the wavelength of the main body moves to the wavelength band of the dopant, it is impossible to obtain light of the desired wavelength according to the type of dopant used.

[0006] Currently, the portable display market is experiencing a trend of increasing in size due to large-area displays, which requires a larger power consumption than conventional portable displays. Therefore, for portable displays with a limited power supply source, namely batteries, power consumption becomes a very important factor, and efficiency and lifespan issues also become important factors that must be addressed.

[0007] Efficiency, lifespan, and driving voltage are interrelated. If efficiency increases, the driving voltage decreases relatively. When the driving voltage is reduced, the crystallization of organic substances based on Joule heating decreases, and ultimately the lifespan tends to increase. However, even if the above organic layer is simply improved, the efficiency cannot be maximized. This is because only when the energy level and T between each organic layer are 1 Only when the optimal combination of value and the inherent properties of the material (mobility, surface properties, etc.) is achieved can long life and high efficiency be achieved at the same time.

[0008] Therefore, it is urgent to develop luminescent materials that have high thermal stability and can effectively achieve charge balance in the luminescent layer. That is, in order to give full play to the excellent characteristics of organic electrical elements, substances that form organic layers in the elements, such as hole injection substances, hole transport substances, luminescent substances, electron transport substances, electron injection substances, etc., should be selected to be supported by stable and effective materials. Summary of the invention

[0009] Technical issues

[0010] An object of the present invention is to provide an organic electrical element and an electronic device thereof, which include a compound capable of reducing the driving voltage of the element and improving the luminous efficiency and lifespan.

[0011] Technical Solution

[0012] In one aspect, the present invention provides an organic electrical device, which includes the compounds represented by Chemical Formula 1 and Chemical Formula 2 in a light-emitting auxiliary layer, and includes the compounds represented by Chemical Formula 3 and Chemical Formula 4 in a light-emitting layer.

[0013]

[0014]

[0015] In another aspect, the present invention provides an electronic device comprising an organic electrical component.

[0016] Effects of the Invention

[0017] The light-emitting auxiliary layer of the present invention includes compounds represented by Chemical Formula 1 and Chemical Formula 2, and the light-emitting layer includes compounds represented by Chemical Formula 3 and Chemical Formula 4, thereby reducing the driving voltage of the organic electrical element and improving the light-emitting efficiency and life of the organic electrical element. BRIEF DESCRIPTION OF THE DRAWINGS

[0018] Figures 1 to 3 This is an illustrative diagram of an organic light emitting device according to an embodiment of the present invention.

[0019] Description of Reference Numerals

[0020] 100, 200, 300: organic electrical element 110: first electrode

[0021] 120: hole injection layer 130: hole transport layer

[0022] 140: Light-emitting 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: first hole transport layer 340: first 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: First stack ST2: Second stack DETAILED DESCRIPTION

[0032] The terms "aryl" and "arylene" used in the present invention have carbon numbers of 6 to 60, unless otherwise specified, but are not limited thereto. In the present invention, aryl or arylene includes monocyclic types, ring aggregates, fused polycyclic types, and spiro compounds.

[0033] The term "fluorenyl" used in the present invention means a substituted or unsubstituted fluorenyl, and "fluorenylene" means a substituted or unsubstituted fluorenylene. The fluorenyl or fluorenylene used in the present invention include spiro compounds formed by mutual bonding between R and R' in the following structure, and also include cyclic compounds formed by mutual bonding between adjacent R". "Substituted fluorenyl" and "substituted fluorenylene" mean that in the following structure, at least one of the substituents R, R', and R" is a substituent other than hydrogen, and R" in the following structure can have a valence of 1 to 8. Regardless of the valence, fluorenyl and fluorenylene can be named as fluorenyl or fluorenyl in this specification.

[0034]

[0035] The term "spiro compound" used in the present invention means "spiro union", and spiro union means that two rings share only one atom to achieve connection. In this case, the atom shared by the two rings is called a "spiro atom", and according to the number of spiro atoms contained in a compound, these are respectively called "monospiro-", "bispiro-", and "trispiro-" compounds.

[0036] The term "heterocyclic group" used in the present invention includes not only aromatic rings such as "heteroaryl" or "heteroarylene" but also non-aromatic rings. Unless otherwise specified, it means a ring having 2 to 60 carbon atoms containing one or more heteroatoms, but the present invention is not limited thereto. The term "heteroatom" used in the present invention, unless otherwise specified, means an element other than carbon, such as N, O, S, P or Si, and may also include SO in place of carbon forming the ring, as in the following compounds: 2 In the present invention, the heterocyclic group means a monocyclic type, a ring aggregate, a fused polycyclic type, a spirocyclic compound, etc. containing a heteroatom.

[0037]

[0038] The term "aliphatic cyclic group" used in the present invention means a cyclic hydrocarbon other than an aromatic hydrocarbon, including a monocyclic type, a ring aggregate, a fused polycyclic type, and a spirocyclic compound, etc. Unless otherwise specified, it means a ring with a carbon number of 3 to 60, but is not limited thereto. For example, when benzene as an aromatic ring and cyclohexane as a non-aromatic ring are fused, it also corresponds to an aliphatic ring.

[0039] In this specification, the "base name" corresponding to the aryl group, arylene group, heterocyclic group, etc. shown as examples of each symbol and its substituent may be recorded as the "base name reflecting the valence", but may also be recorded as the "parent compound name". For example, in the case of "phenanthrene" which is a kind of aryl group, the monovalent "base" is "phenanthryl", the divalent base is "phenanthrylene", etc., and the name of the base may be recorded by distinguishing the valence, but it may be recorded as "phenanthrene" as the name of the parent compound regardless of the valence. Similarly, in the case of pyrimidine, it may be recorded as "pyrimidine" regardless of the valence, or it may be recorded as the "base name" of the valence, for example, in the case of monovalent, it may be recorded as pyrimidinyl, in the case of divalent, it may be recorded as pyrimidinyl, etc.

[0040] In addition, when describing the names of compounds or substituents in the present invention, numerals or letters indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidine may be described as pyridopyrimidine, benzofurano[2,3-d]pyrimidine may be described as benzofuranopyrimidine, 9,9-dimethyl-9H-fluorene may be described as dimethylfluorene, etc. Therefore, benzo[g]quinoxaline or benzo[f]quinoxaline may be described as benzoquinoxaline.

[0041] Furthermore, unless otherwise specified, the chemical formulae used in the present specification can be applied in the same manner as the definitions of substituents defined by the indices in the following chemical formulae.

[0042]

[0043] When a is an integer of 0, the substituent R 1 In the case where a is not present, that is, a is 0, it means that the carbon atoms forming the benzene ring are all bonded with hydrogen atoms. In this case, the representation of the hydrogen atoms bonded to the carbon atoms can be omitted and the chemical formula or compound can be recorded. 1 Combined with one of the carbon atoms forming the benzene ring, when a is an integer of 2 or 3, combined in the following manner, when a is an integer of 4 to 6, combined with the carbon atoms of the benzene ring in a similar manner, when a is an integer of 2 or more, R 1 They may be the same as or different from each other.

[0044]

[0045] Furthermore, in the present specification, unless otherwise specified, a ring means an aromatic ring, a heteroaromatic ring, a fluorene ring, an aliphatic ring, or the like.

[0046] Furthermore, the number-ring may mean a condensed ring, and the number-atom(s) ring may mean the form of a ring. For example, naphthalene is equivalent to a condensed ring of 2 rings, anthracene is equivalent to a condensed ring of 3 rings, thiophene, furan, etc. are equivalent to 5-atomic(s) rings, and benzene and pyridine are equivalent to 6-atomic(s) rings.

[0047] Furthermore, unless otherwise specified in the present specification, the ring formed by the bonding of adjacent groups is selected from C 6 ~C 60 Aromatic ring group; fluorenyl; C containing at least one hetero atom of O, N, S, Si and P 2 ~C 60 A heterocyclic group; and C 3 ~C 60 Here, the aromatic ring group may be an aromatic ring, and the heterocyclic group may include a heteroaromatic ring.

[0048] Unless otherwise specified in this specification, "adjacent groups" means that, when the following chemical formula is used as an example, not only R 1 and R 2 Between 2 and R 3 Between 3 and R 4 Between 5 and R 6 Between, including the R that shares a carbon 7 and R 8 between, and may also include combinations such as R 1 and R 7 Between 1 and R 8 Between or R 4 and R 5 That is, when there is a substituent in a ring-constituent element such as carbon or nitrogen that is not directly adjacent to the ring-constituent element, it can be an adjacent group. However, when there is no substituent in the ring-constituent element at the directly adjacent position, it can be an adjacent group with the substituent bonded to the next ring-constituent element, and the substituents bonded to the same ring-constituent carbon can also be called adjacent groups. In the following chemical formula, the substituents such as R 7 and R 8 When substituents bonded to the same carbon atom bond to each other to form a ring, a compound including a spiro ring portion can be formed.

[0049]

[0050] In the present specification, the expression 'adjacent groups may combine to form a ring' is used with the same meaning as 'adjacent groups combine to selectively form a ring' and means that at least one pair of adjacent groups combine to form a ring.

[0051] In addition, unless otherwise specified in the present specification, an aryl group, an arylene group, a fluorenyl group, a fluorenyl group, a heterocyclic group, an aliphatic cyclic group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, and a ring formed by bonding adjacent groups may be selected from deuterium, halogen, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted amino, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted silyl, C 1 ~C 20 Alkyl or C6 ~C 20 Aryl substituted or unsubstituted phosphine oxide, siloxane, cyano, nitro, C 1 ~C 20 Alkylthio, C 1 ~C 20 Alkoxy, C 6 ~C 20 The aryloxy group, C 6 ~C 20 The arylthio group, C 1 ~C 20 Alkyl, C 2 ~C 20 The alkenyl group, C 2 ~C 20 Alkynyl, C 6 ~C 20 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 20 The heterocyclic group, and C 3 ~C 20 The aliphatic ring group is further substituted by one or more substituents selected from the group consisting of the aliphatic ring group.

[0052] Below, refer to Figures 1 to 3 , the stacked structure of an organic electric device including the compound of the present invention is described.

[0053] In the process of adding reference numerals to the structural elements of each drawing, it is noted that the same structural elements are given the same reference numerals as much as possible even if they are shown in different drawings. In addition, in the process of describing the present invention, if it is judged that the detailed description of the relevant known structure or function will obscure the gist of the present invention, the detailed description will be omitted.

[0054] In the process of describing the structural elements of the present invention, the terms such as first, second, A, B, (a), (b) etc. may be used. Such terms are only used to distinguish from other structural elements, and the nature, order or sequence of the related structural elements will not be limited by such terms. When a structural element is "connected", "combined" or "coupled" to another structural element, the structural element can be directly connected or coupled to the other structural element, but it can also be understood that there are other structural elements "connected", "combined" or "coupled" between the structural elements.

[0055] Furthermore, when a structural element such as a layer, film, region, or plate is located "on" or "above" another structural element, this should be understood not only as being "directly above" the other structural element, but also as being other structural elements in between. Conversely, when a structural element is located "directly above" another part, it should be understood as being without other parts in between.

[0056] Figures 1 to 3 This is an illustrative diagram of an organic light emitting device according to an embodiment of the present invention.

[0057] Reference Figure 1 An organic electrical device 100 according to an embodiment of the present invention includes: a first electrode 110 formed on a substrate (not shown), a second electrode 170 , and an organic layer between the first electrode 110 and the second electrode 170 .

[0058] The first electrode 110 may be an anode, and the second electrode 170 may be a cathode. In the case of an inverted type, the first electrode may be a cathode, and the second electrode may be an anode.

[0059] 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. Specifically, the hole injection layer 120, the hole transport layer 130, the light emitting layer 140, the electron transport layer 150, and the electron injection layer 160 may be sequentially formed on the first electrode 110.

[0060] Preferably, of the two surfaces of the first electrode 110 or the second electrode 170 , a light efficiency improvement layer 180 may be formed on the surface not in contact with the organic layer. When the light efficiency improvement layer 180 is formed, the light efficiency of the organic electrical element may be improved.

[0061] For example, a light efficiency improvement layer 180 may be formed on the second electrode 170. However, in the case of an organic light-emitting element with top emission, the light efficiency improvement layer 180 may reduce the loss of optical energy caused by SPPs (surface plasmon polarizations) in the second electrode 170. In the case of an organic light-emitting element with bottom emission, the light efficiency improvement layer 180 may perform a buffering effect on the second electrode 170.

[0062] 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. Figure 2 Provide explanation.

[0063] Reference Figure 2According to another embodiment of the present invention, an organic electrical element 200 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, which are sequentially formed on a first electrode 110, and a light efficiency improvement layer 180 may be formed on the second electrode.

[0064] Although not shown in Figure 2 An electron transport auxiliary layer may be further formed between the light emitting layer 140 and the electron transport layer 150 .

[0065] In addition, according to another embodiment of the present invention, the organic layer may also be in the form of a stack of a plurality of hole transport layers, a light emitting layer, and an electron transport layer. Figure 3 Provide explanation.

[0066] Reference Figure 3 According to another embodiment of the present invention, the organic electrical element 300 may be formed with two or more stacks of organic layers (ST1, ST2) formed in multiple layers between the first electrode 110 and the second electrode 170, and a charge generation layer CGL is formed between the stacks of organic layers.

[0067] Specifically, the organic electrical device according to an embodiment of the present invention may include a first electrode 110 , a first stack ST1 , a charge generation layer CGL (Charge Generation Layer), a second stack ST2 , a second electrode 170 , and a light efficiency improvement layer 180 .

[0068] The first stack ST1, as an organic layer formed on the first electrode 110, 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. In this way, the first stack and the second stack may have organic layers with the same stacked structure, or may have organic layers with different stacked structures.

[0069] 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. The 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 smoothly distribute charges.

[0070] Although the first light-emitting layer 340 may include a light-emitting material containing a blue fluorescent dopant in a blue main body, and the second light-emitting layer 440 may include a material in which a green main body is doped with a greenish yellow dopant and a red dopant, 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.

[0071] exist Figure 3 In the embodiment, n may be an integer of 1 to 5. However, when n is 2, a charge generation layer CGL and a third stack may be further stacked on the second stack ST2.

[0072] like Figure 3 By forming multiple light-emitting layers by means of a multi-layer stacking structure, it is possible to prepare not only an organic electrical light-emitting element that emits white light by means of a mixing effect of light emitted by each light-emitting layer, but also an organic electrical light-emitting element that emits light of multiple colors.

[0073] The compounds represented by Chemical Formula 1 to Chemical Formula 4 of the present invention may be included in the organic layer. For example, although the compounds represented by Chemical Formula 1 to Chemical Formula 4 of the present invention may be used as materials for the hole injection layer 120, 320, 420, the hole transport layer 130, 330, 430, the buffer layer 210, the luminescent auxiliary layer 220, the electron transport layer 150, 350, 450, the electron injection layer 160, the luminescent layer 140, 340, 440, or the light efficiency improvement layer 180, preferably, although the compound represented by Chemical Formula 1 or Chemical Formula 2 may be used as the material of the luminescent auxiliary layer 220, and although the compound represented by Chemical Formula 3 or Chemical Formula 4 may be used as the material of the luminescent layer 140, 340, 440.

[0074] Even for the same or similar cores, the band gap, electrical properties, surface properties, etc. may differ depending on which substituent is bonded at which position, so it is necessary to study the selection of the core and the combination of the sub-substituents bonded to it. In particular, when the energy level between the organic layers and T 1 When the optimal combination of the intrinsic properties of the material (mobility, surface properties, etc.) is achieved, long life and high efficiency can be achieved at the same time.

[0075] Therefore, the compound represented by Chemical Formula 1 or Chemical Formula 2 in the present invention is used as the light-emitting auxiliary layer 220, and the compound represented by Chemical Formula 3 or Chemical Formula 4 in the present invention is used as the material of the light-emitting layers 140, 340, 440, so that the energy level between the organic layers and T 1 The value, inherent properties (mobility, surface properties, etc.) are optimized, while the life and efficiency of organic electrical components are improved.

[0076] The organic light-emitting element of one embodiment of the present invention can be prepared by various evaporation methods. It can be prepared by evaporation methods such as PVD or CVD. For example, the anode 110 can be formed by evaporating a metal or a conductive metal oxide or an alloy thereof on a substrate, and 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 is formed thereon, and then a substance that can be used as a cathode 170 is evaporated thereon. In addition, a light-emitting auxiliary layer 220 can be formed between the hole transport layer 130 and the light-emitting layer 140, and an electron transport auxiliary layer (not shown) can be formed between the light-emitting layer 140 and the electron transport layer 150. As described above, it can also be formed in a stacked structure.

[0077] Furthermore, the organic layer uses a variety of polymer materials and is formed into a smaller number of layers by a solvent treatment or solvent refining method other than the evaporation method, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slit coating process, a dip coating process, a roll-to-roll process, a doctor blade process, a screen printing process, or a thermal transfer method. Since the organic layer of the present invention can be formed by a variety of methods, the protection scope of the present invention is not limited by the formation method.

[0078] The organic electrical device according to an embodiment of the present invention can be classified into a front-emitting type, a rear-emitting type or a double-emitting type according to the materials used.

[0079] Furthermore, the organic electrical device according to an embodiment of the present invention is selected from the group consisting of an organic electrical light-emitting device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device, and a quantum dot display device.

[0080] Another embodiment of the present invention may include an electronic device, the electronic device including: a display device including the organic electrical element of the present invention; and a control unit for controlling 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 devices, game consoles, various TVs, and various computers.

[0081] Hereinafter, an organic electric device according to one aspect of the present invention will be described.

[0082] According to one aspect of the present invention, the present invention provides an organic electrical element, which includes a first electrode, a second electrode and an organic layer formed between the first electrode and the second electrode. The organic layer includes: a light-emitting layer, a hole transport layer formed between the first electrode and the light-emitting layer, and a light-emitting auxiliary layer formed between the hole transport layer and the light-emitting layer, and the light-emitting auxiliary layer includes compounds represented by the following chemical formulas 1 and 2, and the light-emitting layer includes compounds represented by the following chemical formulas 3 and 4.

[0083] The above-mentioned luminescence auxiliary layer may include at least two of the compounds represented by the following Chemical Formula 1 or Chemical Formula 2. In addition, the above-mentioned luminescence auxiliary layer includes a first luminescence auxiliary layer adjacent to the above-mentioned hole transport layer and a second luminescence auxiliary layer adjacent to the above-mentioned luminescent layer, and the first luminescence auxiliary layer and the second luminescence auxiliary layer may each include a compound represented by the following Chemical Formula 1 or Chemical Formula 2.

[0084] In addition, the light emitting layer may include at least two of the compounds represented by the following Chemical Formula 3 or Chemical Formula 4. In this case, the compound represented by the following Chemical Formula 3 and the compound represented by the following Chemical Formula 4 may be mixed in a weight ratio of 1:9 to 9:1.

[0085]

[0086] In addition, the hole transport layer of the present invention may include a compound represented by Chemical Formula 5 below.

[0087] <Chemical Formula 5>

[0088]

[0089] In addition, the organic layer of the present invention may include an electron transport layer formed between the second electrode and the light emitting layer. In this case, the electron transport layer may include a compound represented by the following Chemical Formula 6.

[0090] <Chemical Formula 6>

[0091]

[0092] Hereinafter, the above-mentioned Chemical Formulas 1 to 6 will be described.

[0093] In the above Chemical Formulae 1 to 6, each symbol can be defined as follows.

[0094] Ar 1 To Ar 17 Independently selected from C 6 ~C 60 aryl; fluorenyl; C containing at least one heteroatom selected from O, N, S, Si and P 2 ~C60 A heterocyclic group; and C 3 ~C 60 A group consisting of aliphatic ring groups.

[0095] L 1 To L 15 , L a , L b , L c are independently selected from single bonds; C 6 ~C 60 arylene; fluorene; C 3 ~C 60 and a C containing at least one heteroatom selected from O, N, S, Si and P 2 ~C 60 A group consisting of a heterocyclic group.

[0096] In Chemical Formula 2, X is O, S, C (R 1 )(R 2 ) or N(R 3 ), in chemical formula 6, X 1 To X 3 Independently of each other, C(R 11 ) or N, at least one of which is N.

[0097] In Chemical Formula 4, Ring A and Ring B are independently an aryl ring or a heteroaryl ring, and at least one of Ring A and Ring B is C 10 The above aromatic rings, ring A and ring B may be each replaced by one or more R 4 replace.

[0098] R 1 To R 4 , R 30 , R 31 , R 1 , R 2 , R 4 , R 11 , R e , R f independently selected from hydrogen; deuterium; halogen; cyano; C 6 ~C 60 aryl; fluorenyl; C containing at least one heteroatom selected from O, N, S, Si and P 2 ~C 60 Heterocyclic group; C 3 ~C 60 Aliphatic ring group; C 1 ~C 20 Alkyl; C 2 ~C 20 Alkenyl; C 2~C 20 Alkynyl; C 1 ~C 30 Alkoxy; C 6 ~C 20 aryloxy; and -L'-N(R a )(R b ), and adjacent groups can be combined with each other to form a ring, R e and R f They can combine with each other to form a ring, R 1 and R 2 They can combine with each other to form a ring. e and R f Between 1 and R 2 When the two radicals can be combined with each other to form a ring, a spiro compound can be formed.

[0099] a, b and b1 are each an integer of 0 to 3, c is an integer of 0 to 6, d and a1 are each an integer of 0 to 4, and when they are each an integer of 2 or more, R 1 Respectively, R 2 Respectively, R 3 Respectively, R 4 Respectively, R 30 Respectively, R 31 The same or different respectively.

[0100] Between adjacent groups, for example, adjacent R 1 Between, adjacent R 2 Between, adjacent R 3 Between or adjacent R 4 Between, adjacent R 30 Between, adjacent R 31 When they are combined to form a ring, the ring can be selected from C 6 ~C 60 Aromatic ring group; fluorene ring group; C containing at least one hetero atom of O, N, S, Si and P 2 ~C 60 A heterocyclic group; and C 3 ~C 60 A group consisting of aliphatic ring groups.

[0101] When the ring formed by the mutual bonding of adjacent groups is an aromatic ring, the aromatic ring may be C 6 ~C 20 , C 6 ~C 18 , C 6 ~C 16 , C 6 ~C14 , C 6 ~C 13 , C 6 ~C 12 , C 6 ~C 10 , C 6 , C 10 , C 12 , C 14 , C 15 , C 16 , C 18 The aromatic ring is an aromatic ring of, for example, benzene, naphthalene, anthracene, phenanthrene, pyrene or the like.

[0102] The above R 3 To choose free C 6 ~C 60 aryl; fluorenyl; C containing at least one heteroatom selected from O, N, S, Si and P 2 ~C 60 A heterocyclic group; and C 3 ~C 60 A group consisting of aliphatic ring groups.

[0103] The above L' is selected from a single bond; 6 ~C 60 arylene; fluorene; C 3 ~C 60 and a C containing at least one heteroatom selected from O, N, S, Si and P 2 ~C 60 A group consisting of a heterocyclic group.

[0104] The above R a and R b Independently selected from C 6 ~C 60 aryl; fluorenyl; C containing at least one heteroatom selected from O, N, S, Si and P 2 ~C 60 A heterocyclic group; and C 3 ~C 60 A group consisting of aliphatic ring groups.

[0105] In the above Ar 1 To Ar 17 , R 1 To R 4 , R 30 , R 31 , R 1 To R 4 , R 11 , R a , R b , R e, R f When at least one of the groups is an aryl group, the aryl group may be, for example, C 6 ~C 30 , C 6 ~C 29 , C 6 ~C 28 , C 6 ~C 27 , C 6 ~C 26 , C 6 ~C 25 , C 6 ~C 24 , C 6 ~C 23 , C 6 ~C 22 , C 6 ~C 21 , C 6 ~C 20 , C 6 ~C 19 , C 6 ~C 18 , C 6 ~C 17 , C 6 ~C 16 , C 6 ~C 15 , C 6 ~C 14 , C 6 ~C 13 , C 6 ~C 12 , C 6 ~C 11 , C 6 ~C 10 , C 6 , C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 Specifically, the aromatic group may be phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, triphenylene, or the like.

[0106] In the above L 1 To L 15 , L a , L b , L cWhen at least one of L and L' is an arylene group, the arylene group may be, for example, C 6 ~C 30 , C 6 ~C 29 , C 6 ~C 28 , C 6 ~C 27 , C 6 ~C 26 , C 6 ~C 25 , C 6 ~C 24 , C 6 ~C 23 , C 6 ~C 22 , C 6 ~C 21 , C 6 ~C 20 , C 6 ~C 19 , C 6 ~C 18 , C 6 ~C 17 , C 6 ~C 16 , C 6 ~C 15 , C 6 ~C 14 , C 6 ~C 13 , C 6 ~C 12 , C 6 ~C 11 , C 6 ~C 10 , C 6 , C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 Specifically, the arylene group may be phenylene, biphenyl, naphthylene, terphenyl, phenanthrene, triphenylene, or the like.

[0107] In the above Ar 1 To Ar 17 , R 1 To R 4 , R 30, R 31 , R 1 To R 4 , R 11 , R a , R b , R e , R f , L 1 To L 15 , L a , L b , L c When at least one of L and L' is a heterocyclic group, the heterocyclic group may be, for example, C 2 ~C 30 , C 2 ~C 29 , C 2 ~C 28 , C 2 ~C 27 , C 2 ~C 26 , C 2 ~C 25 , C 2 ~C 24 , C 2 ~C 23 , C 2 ~C 22 , C 2 ~C 21 , C 2 ~C 20 , C 2 ~C 19 , C 2 ~C 18 , C 2 ~C 17 , C 2 ~C 16 , C 2 ~C 15 , C 2 ~C 14 , C 2 ~C 13 , C 2 ~C 12 , C 2 ~C 11 , C 2 ~C 10 , C 2 ~C 9 , C 2 ~C 8 , C 2 ~C 7 , C 2 ~C 6 , C 2 ~C 5, C 2 ~C 4 , C 2 ~C 3 , C 2 , C 3 , C 4 , C 5 , C 6 , C 7 , C 8 , C 9 , 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 29 The heterocyclic group of the present invention can be pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, thiorrole, indene, indole, phenyl-indole, benzindole, phenyl-benzoindole, pyrazinoindole, quinoline, isoquinoline, benzoquinoline, pyridoquinoline, quinazoline, benzoquinazoline, dibenzoquinazoline, phenanthroquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, benzofuran, naphthobenzofuran, dibenzofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthobenzothiophene, dinaphthothiophene, carbazole, benz-carbazole, benzocarbazole, benz-benzocarbazole, naphthalene-benzocarbazole , dibenzocarbazole, indolecarbazole, benzofuranopyridine, benzothienopyridine, benzofuranopyridine, benzothienopyrimidine, benzofuranopyrimidine, benzothienopyrazine, benzofuranopyrazine, benzimidazole, benzothiazole, benzoxazole, benzosilole, phenanthroline, dihydro-phenylphenazine, 10-phenyl-10H-phenoxazine, phenoxazine, phenothiazine, dibenzodioxine, benzodibenzodioxine, thianthrene, 9,9-dimethyl-9H-xanthene, 9,9-dimethyl-9H-thioxanthene, dihydrodimethylphenylacridine, spiro[fluorene-9,9'-xanthene], etc.

[0108] In the above Ar 1 To Ar 17 , R 1 To R 4 , R 30 , R31 , R 1 To R 4 , R 11 , R a , R b , R e , R f At least one of them is fluorenyl or L 1 To L 15 , L a , L b , L c When at least one of L and L' is a fluorenyl group, the fluorenyl group or fluorenyl group can 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-(naphthalen-2-yl)9-phenyl-9H-fluorene, etc.

[0109] In the above R 1 To R 4 , R 30 , R 31 , R 1 , R 2 , R 4 , R 11 , R e , R f When at least one of the alkyl groups is an alkyl group, the alkyl group may be, for example, C 1 ~C 20 , C 1 ~C 10 , C 1 ~C 4 , C 1 , C 2 , C 3 , C 4 The alkyl group may be, for example, a methyl group, an ethyl group, a tert-butyl group, etc.

[0110] In the above R 1 To R 4 , R 30 , R 31 , R 1 , R 2 , R 4 , R 11 , R e , R f When at least one of the alkoxy groups is an alkoxy group, the alkoxy group may be, for example, C 1 ~C 20 , C 1 ~C 10 , C 1 ~C 4 , C1 , C 2 , C 3 , C 4 The alkoxy group of the above mentioned group may be, for example, a methoxy group, an ethoxy group, or the like.

[0111] In the above Chemical Formulas 1 to 6, the above aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, and adjacent groups are combined to form a ring, R e and R f They can combine with each other to form a ring, and R 1 and R 2 They can be combined with each other to form a ring, which can be selected from deuterium, halogen, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted silyl, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted phosphine oxide, siloxane, cyano, nitro, C 1 ~C 20 Alkylthio, C 1 ~C 20 Alkoxy, C 6 ~C 20 The aryloxy group, C 6 ~C 20 The arylthio group, C 1 ~C 20 Alkyl, C 2 ~C 20 The alkenyl group, C 2 ~C 20 Alkynyl, C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 The heterocyclic group, and C 3 ~C 30 The aliphatic ring group is further substituted by one or more substituents selected from the group consisting of the aliphatic ring group.

[0112] The above aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, and adjacent groups are combined to form a ring, R e and R f They can combine with each other to form a ring, and R 1 and R 2When at least one of the rings can be further substituted with an aryl group, the aryl group can be, for example, C 6 ~C 30 , C 6 ~C 29 , C 6 ~C 28 , C 6 ~C 27 , C 6 ~C 26 , C 6 ~C 25 , C 6 ~C 24 , C 6 ~C 23 , C 6 ~C 22 , C 6 ~C 21 , C 6 ~C 20 , C 6 ~C 19 , C 6 ~C 18 , C 6 ~C 17 , C 6 ~C 16 , C 6 ~C 15 , C 6 ~C 14 , C 6 ~C 13 , C 6 ~C 12 , C 6 ~C 11 , C 6 ~C 10 , C 6 , C 10 , 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 29 , C 30 Etc. aromatic groups.

[0113] The above aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, and adjacent groups are combined to form a ring, R e and R f They can combine with each other to form a ring, and R 1 and R 2 When at least one of the rings may be further substituted by a heterocyclic group, the heterocyclic group may be, for example, C 2 ~C 30 , C 2 ~C 29 , C 2 ~C 28 , C 2 ~C 27 , C 2 ~C 26 , C 2 ~C 25 , C 2 ~C 24 , C 2 ~C 23 , C 2 ~C 22 , C 2 ~C 21 , C 2 ~C 20 , C 2 ~C 19 , C 2 ~C 18 , C 2 ~C 17 , C 2 ~C 16 , C 2 ~C 15 , C 2 ~C 14 , C 2 ~C 13 , C 2 ~C 12 , C 2 ~C 11 , C 2 ~C 10 , C 2 ~C 9 , C 2 ~C 8 , C 2 ~C 7 , C 2 ~C 6 , C 2 ~C 5 , C 2 ~C 4 , C2 ~C 3 , C 2 , C 3 , C 4 , C 5 , C 6 , C 7 , C 8 , C 9 , 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 29 , C 30 Heterocyclic groups such as those of

[0114] The above aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, and adjacent groups are combined to form a ring, R e and R f They can combine with each other to form a ring, and R 1 and R 2 When at least one of the groups that can be combined with each other to form a ring is further substituted with a fluorenyl group, the fluorenyl group can 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-(naphthalen-2-yl)9-phenyl-9H-fluorene, etc.

[0115] The above aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, and adjacent groups are combined to form a ring, R e and R f They can combine with each other to form a ring, and R 1 and R 2 When at least one of the rings may be further substituted by an aliphatic ring group, the aliphatic ring group may be, for example, C 3 ~C 20 , C3 ~C 19 , C 3 ~C 18 , C 3 ~C 17 , C 3 ~C 16 , C 3 ~C 15 , C 3 ~C 14 , C 3 ~C 13 , C 3 ~C 12 , C 3 ~C 11 , C 3 ~C 10 , C 3 ~C 8 , C 3 ~C 6 , C 6 , C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 Aliphatic cyclic groups such as the above.

[0116] The above aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, and adjacent groups are combined to form a ring, R e and R f They can combine with each other to form a ring, and R 1 and R 2 When at least one of the rings is further substituted by an alkyl group, the alkyl group may be, for example, C 1 ~C 20 , C 1 ~C 10 , C 1 ~C 4 , C 1 , C 2 , C 3 , C 4 etc.

[0117] The above aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, and adjacent groups are combined to form a ring, R e and R f They can combine with each other to form a ring, and R1 and R 2 When at least one of the rings is further substituted by an alkoxy group, the alkoxy group may be, for example, C 1 ~C 20 , C 1 ~C 10 , C 1 ~C 4 , C 1 , C 2 , C 3 , C 4 Alkoxy etc.

[0118] The above aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, and adjacent groups are combined to form a ring, R e and R f They can combine with each other to form a ring, and R 1 and R 2 When at least one of the rings may be further substituted with an aryloxy group, the aryloxy group may be, for example, C 6 ~C 30 , C 6 ~C 29 , C 6 ~C 28 , C 6 ~C 27 , C 6 ~C 26 , C 6 ~C 25 , C 6 ~C 24 , C 6 ~C 23 , C 6 ~C 22 , C 6 ~C 21 , C 6 ~C 20 , C 6 ~C 19 , C 6 ~C 18 , C 6 ~C 17 , C 6 ~C 16 , C 6 ~C 15 , C 6 ~C 14 , C 6 ~C 13 , C 6 ~C 12 , C6 ~C 11 , C 6 ~C 10 , C 6 , C 10 , 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 29 , C 30 Etc. aryloxy, etc.

[0119] The compound represented by the above Chemical Formula 1 may be represented by one of the following Chemical Formula 1-1 or Chemical Formula 1-9.

[0120]

[0121]

[0122] In the above Chemical Formulas 1-1 to 1-9, Ar 2 ,Ar 3 , L 1 To L 3 Same as the definition in Chemical Formula 1, Y 1 To Y 3 O, S, C (R 5 )(R 6 ) or N(R 7 ).

[0123] R 5 To R 12 , R', R", R 5 , R 6 independently selected from hydrogen, deutrium, halogen, 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted silyl, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted phosphine oxide, siloxane, cyano, nitro, C1 ~C 20 Alkylthio, C 1 ~C 20 Alkoxy, C 6 ~C 20 The aryloxy group, C 6 ~C 20 The arylthio group, C 1 ~C 20 Alkyl, C 2 ~C 20 The alkenyl group, C 2 ~C 20 Alkynyl, C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 The heterocyclic group, and C 3 ~C 30 The adjacent groups can be combined with each other to form a ring. 5 and R 6 They can be combined with each other to form a ring, and R' and R" can be combined with each other to form a ring.

[0124] R a and R b Independently of each other 1 ~C 20 of alkyl.

[0125] The above R 7 To choose free C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 The heterocyclic group, and C 3 ~C 30 A group consisting of aliphatic ring groups.

[0126] e, f, h, i, l, o, p are each an integer from 0 to 4, g, j, k are each an integer from 0 to 3, m and n are each an integer from 0 to 5, and when they are each an integer of 2 or more, R 5 Respectively, R 6 Respectively, R 7 Respectively, R 8 Respectively, R 9 Respectively, R 10 Respectively, R 11 Respectively, R 12 Respectively, R 13 Respectively, R 14 The same or different respectively.

[0127] The compound represented by the above Chemical Formula 2 may be represented by one of the following Chemical Formula 2-1 or Chemical Formula 2-5.

[0128]

[0129]

[0130] In the above Chemical Formulas 2-1 to 2-5, X, Ar 4 To Ar 7 , L 4 To L 9 , R 1 , R 2 , a, b are the same as those in Chemical Formula 2, Y 4 O, S, C (R 8 )(R 9 ) or N(R 10 ).

[0131] R 15 , R 16 , R 8 , R 9 independently selected from hydrogen, deutrium, halogen, 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted silyl, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted phosphine oxide, siloxane, cyano, nitro, C 1 ~C 20 Alkylthio, C 1 ~C 20 Alkoxy, C 6 ~C 20 The aryloxy group, C 6 ~C 20 The arylthio group, C 1 ~C 20 Alkyl, C 2 ~C 20 The alkenyl group, C 2 ~C 20 Alkynyl, C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 The heterocyclic group, and C 3 ~C 30The adjacent groups can be combined with each other to form a ring. 8 and R 9 They can combine with each other to form a ring.

[0132] The above R 10 To choose free C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 The heterocyclic group, and C 3 ~C 30 A group consisting of aliphatic ring groups.

[0133] q is an integer of 0 to 3, r is an integer of 0 to 4, and when they are respectively integers of 2 or more, R 15 Respectively, R 16 The same or different respectively.

[0134] The compound represented by the above Chemical Formula 3 may be represented by one of the following Chemical Formula 3-1 or Chemical Formula 3-8.

[0135]

[0136]

[0137] In the above Chemical Formulae 3-1 to 3-8, Ar 8 To Ar 10 , L a , R 3 and c are the same as defined in the above chemical formula 3.

[0138] R 17 To R 20 independently selected from hydrogen, deutrium, halogen, 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted silyl, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted phosphine oxide, siloxane, cyano, nitro, C 1 ~C 20 Alkylthio, C 1 ~C 20 Alkoxy, C 6 ~C 20 The aryloxy group, C 6 ~C 20 The arylthio group, C 1~C 20 Alkyl, C 2 ~C 20 The alkenyl group, C 2 ~C 20 Alkynyl, C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 The heterocyclic group, and C 3 ~C 30 The adjacent groups can be combined with each other to form a ring.

[0139] s, u, and v are integers of 0 to 4, and t is an integer of 0 to 6. When they are integers of 2 or more, R 17 Respectively, R 18 Respectively, R 19 Respectively, R 20 The same or different respectively.

[0140] The compound represented by the above Chemical Formula 4 may be represented by one of the following Chemical Formula 4-1 or Chemical Formula 4-13.

[0141]

[0142]

[0143]

[0144] In the above Chemical Formulas 4-1 to 4-13, Ring A, Ring B, L b , L c ,Ar 11 ,Ar 12 , R 4 , d are the same as those defined in the above chemical formula 4, R 21 and R 22 R in the above chemical formula 4 1 w is an integer of 0 to 6, x is an integer of 0 to 2, and y is an integer of 0 to 4, and when they are respectively integers of 2 or more, R 21 Respectively, R 22 The adjacent groups may be the same or different and may be combined with each other to form a ring.

[0145] The compound represented by the above Chemical Formula 5 can be represented by the following Chemical Formula 5-1.

[0146] <Chemical Formula 5-1>

[0147]

[0148] In the above chemical formula 5-1, R 30 , R 31 , a1, b1, R e , R f , L 11 , L 12 ,Ar 13 ,Ar 14 Same as defined in the above Chemical Formula 5.

[0149] The compound represented by the above Chemical Formula 6 may be represented by one of the following Chemical Formula 6-1 or Chemical Formula 6-3.

[0150]

[0151]

[0152] In the above Chemical Formulae 6-1 to 6-3, X 1 To X 3 , L 13 To L 15 ,Ar 16 ,Ar 17 Same as the definition in the above Chemical Formula 6.

[0153] X 4 and X 5 O, S, C (R 21 )(R 22 ) or N(R 23 ), and X 4 and X 5 At least one of X is not a single bond. 6 and X 7 For single bond O, S, C(R 21 )(R 22 ) or N(R 23 ).

[0154] R 32 To R 37 , R 21 , R 22 independently selected from hydrogen, deutrium, halogen, 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted silyl, C 1 ~C 20 Alkyl or C 6 ~C 20 Aryl substituted or unsubstituted phosphine oxide, siloxane, cyano, nitro, C 1 ~C 20 Alkylthio, C1 ~C 20 Alkoxy, C 6 ~C 20 The aryloxy group, C 6 ~C 20 The arylthio group, C 1 ~C 20 Alkyl, C 2 ~C 20 The alkenyl group, C 2 ~C 20 Alkynyl, C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 The heterocyclic group, and C 3 ~C 30 The adjacent groups can be combined with each other to form a ring. 21 and R 22 They can combine with each other to form a ring.

[0155] c1, e1, f1, g1, h1 are integers of 0 to 4, d1 is an integer of 0 to 3, and when they are integers of 2 or more, R 32 Respectively, R 33 Respectively, R 34 Respectively, R 35 Respectively, R 36 Respectively, R 37 The same or different respectively.

[0156] The above R 23 To choose free C 6 ~C 30 an aryl group, a fluorenyl group, a C group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 2 ~C 30 The heterocyclic group, and C 3 ~C 30 A group consisting of aliphatic ring groups.

[0157] Specifically, the compound represented by the above Chemical Formula 1 may be one of the following compounds, but is not limited thereto.

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164] Specifically, the compound represented by the above Chemical Formula 2 may be one of the following compounds, but is not limited thereto.

[0165]

[0166]

[0167] Specifically, the compound represented by the above Chemical Formula 3 may be one of the following compounds, but is not limited thereto.

[0168]

[0169]

[0170]

[0171]

[0172]

[0173] Specifically, the compound represented by the above Chemical Formula 4 may be one of the following compounds, but is not limited thereto.

[0174]

[0175]

[0176]

[0177]

[0178] Specifically, the compound represented by Chemical Formula 5 may be one of Compounds 1-37 to 1-60, 1-75, 1-77, 1-81, 1-85, 1-87, 1-90, 1-91, 1-93, 1-94, 1-96, 1-97, 1-101 to 1-108, but is not limited thereto.

[0179] Specifically, the compound represented by the above Chemical Formula 6 may be one of the following compounds, but is not limited thereto.

[0180]

[0181]

[0182] Hereinafter, examples are given to specifically illustrate the synthesis examples of the compounds represented by Chemical Formula 1 to Chemical Formula 6 and the preparation examples of the organic electroluminescent device of the present invention, but the present invention is not limited to the following examples.

[0183] [Synthesis Example 1] Synthesis Example of Chemical Formula 1

[0184] The compound represented by Chemical Formula 1 according to the present invention (final product 1) can be synthesized as shown in the following Reaction Formula 1, but is not limited thereto.

[0185] <Reaction Formula 1> (Hal is I, Br or Cl.)

[0186]

[0187] Example compounds of Sub1

[0188]

[0189] The compounds belonging to Sub1 may be the same compounds as the following compounds, but are not limited thereto. The FD-MS (Field Desorption-Mass Spectrometry) values ​​of the following compounds are shown in Table 1.

[0190]

[0191]

[0192]

[0193] [Table 1]

[0194]

[0195]

[0196] Example compounds of Sub2

[0197] Sub2 according to Reaction Formula 1 can be synthesized through the reaction pathway of the following Reaction Formula 2 (disclosed in Korean Patent No. 10-1251451 (registration announcement on April 5, 2013) of the present applicant), but is not limited thereto.

[0198] <Reaction Formula 2> (Hal is I, Br or Cl.)

[0199]

[0200] The compounds belonging to Sub2 may be the same compounds as those described below, but are not limited thereto. The FD-MS values ​​of the following compounds are shown in Table 2.

[0201]

[0202]

[0203]

[0204] [Table 2]

[0205]

[0206]

[0207] Synthesis example of final product

[0208] 1.1-7 Synthesis Example

[0209]

[0210] Sub1-18 (10.0 g, 24.4 mmol) was dissolved in toluene (122 mL), and then Sub2-18 (10.3 g, 24.4 mmol), Pd 2 (dba) 3 (0.67 g, 0.73 mmol), P(t-Bu) 3 (0.30 g, 1.47 mmol), NaOt-Bu (4.7 g, 48.9 mmol), and stirred at 80 °C. After the reaction was completed, CH 2 Cl 2 After extraction with water, the organic layer was concentrated with MgSO 4 After drying, the concentrate was concentrated, and then separated by a silica gel column and recrystallized to obtain 13.2 g (yield: 72%) of a product.

[0211] Synthesis Example of 2.1-13

[0212]

[0213] Sub1-80 (10.0 g, 25.1 mmol) was dissolved in toluene (126 mL), and then Sub2-12 (8.1 g, 25.1 mmol), Pd 2 (dba) 3 (0.69 g, 0.75 mmol), P(t-Bu) 3 (0.30 g, 1.51 mmol) and NaOt-Bu (4.8 g, 50.2 mmol) were added and purified after the reaction in the same manner as in the synthesis of 1-7 to obtain 12.5 g of a product (yield: 78%).

[0214] Synthesis Example of 3.1-28

[0215]

[0216] Sub1-93 (10.0 g, 33.7 mmol) was dissolved in toluene (168 mL), and then Sub2-72 (11.8 g, 33.7 mmol), Pd 2 (dba) 3 (0.92 g, 1.01 mmol), P(t-Bu) 3 (0.41 g, 2.02 mmol) and NaOt-Bu (6.5 g, 67.3 mmol) were added and purified after the reaction in the same manner as in the synthesis method of 1-7 to obtain 15.1 g of a product (yield: 79%).

[0217] Synthesis Example of 4.1-32

[0218]

[0219] Sub1-104 (10.0 g, 22.5 mmol) was dissolved in toluene (112 mL), and then Sub2-12 (7.2 g, 22.5 mmol), Pd 2 (dba) 3 (0.62 g, 0.67 mmol), P(t-Bu) 3 (0.27 g, 1.35 mmol) and NaOt-Bu (4.3 g, 44.9 mmol) were added and purified after the reaction in the same manner as in the synthesis of 1-7 to obtain 11.4 g of a product (yield: 74%).

[0220] Synthesis Example of 5.1-49

[0221]

[0222] Sub1-73 (10.0 g, 31.0 mmol) was dissolved in toluene (155 mL), and then Sub2-42 (12.7 g, 31.0 mmol), Pd 2 (dba) 3 (0.85 g, 0.93 mmol), P(t-Bu) 3 (0.38 g, 1.86 mmol) and NaOt-Bu (6.0 g, 62.1 mmol) were added and purified after the reaction in the same manner as in the synthesis method of 1-7 to obtain 14.3 g of a product (yield: 71%).

[0223] Synthesis Example of 6.1-104

[0224]

[0225] Sub1-54 (10.0 g, 21.2 mmol) was dissolved in toluene (106 mL), and then Sub2-31 (7.7 g, 21.2 mmol), Pd 2 (dba) 3 (0.58 g, 0.64 mmol), P(t-Bu) 3 (0.26 g, 1.27 mmol) and NaOt-Bu (4.1 g, 42.4 mmol) were added and purified after the reaction in the same manner as in the synthesis of 1-7 to obtain 10.4 g of a product (yield: 65%).

[0226] The FD-MS values ​​of the compounds 1-1 to 1-108 of the present invention prepared according to the above-mentioned Synthesis Examples are shown in Table 3 below.

[0227] [Table 3]

[0228]

[0229]

[0230] [Synthesis Example 2] Synthesis Example of Chemical Formula 2

[0231] The compound represented by Chemical Formula 2 according to the present invention (final product 2) is synthesized as shown in the following Reaction Formula 3, but is not limited thereto.

[0232] <Reaction 3>

[0233]

[0234] Example compounds of Sub3

[0235] The compounds belonging to Sub3 may be the same compounds as the following compounds, but are not limited thereto. The FD-MS values ​​of the following compounds are shown in Table 4.

[0236]

[0237] [Table 4]

[0238] Compound FD-MS Compound FFD-MS Sub3-1 <![CDATA[m / z=295.91(C 12 H 6 BrClS=297.59)]]> Sub3-2 <![CDATA[m / z=371.94(C 18 H 10 BrClS=373.69)]]> Sub3-3 <![CDATA[m / z=279.93(C 12 H 6 BrCl0=281.53)]]> Sub3-4 <![CDATA[m / z=295.91(C 12 H 6 BrClS=297.59)]]> Sub3-5 <![CDATA[m / z=279.93(C1 2 H 6 BrCl0=281.53)]]> Sub3-6 <![CDATA[m / z=295.91(C 12 H 6 BrClS=297.59)]]> Sub3-7 <![CDATA[m / z=371.94(C 18 H 10 BrClS=373.69)]]> Sub3-8 <![CDATA[m / z=279.93(C 12 H 6 BrCl0=281.53)]]> Sub3-9 <![CDATA[m / z=329.94(C 16 H 8 BrCl0=331.59)]]> Sub3-10 <![CDATA[m / z=295.91(C 12 H 6 BrClS=297.59)]]> Sub3-11 <![CDATA[m / z=497.98(C 28 H 16 BrClS=499.85)]]> Sub3-12 <![CDATA[m / z=279.93(C 12 H 6 BrCl0=281.53)]]> Sub3-13 <![CDATA[m / z=355.96(C 18 H 10 BrCl0=357.63)]]> Sub3-14 <![CDATA[m / z=295.91(C 12 H 6 BrClS=297.59)]]> Sub315 <![CDATA[m / z=279.93(C 12 H 6 BrCl0=281.53)]]> Sub316 <![CDATA[m / z=329.94(C 16 H 8 BrCl0=331.59)]]> Sub3-17 <![CDATA[m / z=295.91(C 12 H 6 BrClS=297.59)]]> Sub3-18 <![CDATA[m / z=371.94(C 18 H 10 BrClS=373.69)]]> Sub3-19 <![CDATA[m / z=345.92(C 16 H 8 BrClS=347.65)]]> Sub3-20 <![CDATA[m / z=279.93(C 12 H 6 BrCl0=281.53)]]> Sub321 <![CDATA[m / z=295.91(C 12 H 6 BrClS=297.59)]]> Sub322 <![CDATA[m / z=471.97(C 26 H 14 BrClS=473.81)]]> Sub3-23 <![CDATA[m / z=279.93(C 12 H 6 BrCl0=281.53)]]> Sub3-24 <![CDATA[m / z=405.98(C 22 H 12 BrCl0=407.69)]]> Sub3-25 <![CDATA[m / z=295.91(C 12 H 6 BrClS=297.59)]]> Sub3-26 <![CDATA[m / z=279.93(C 12 H 6 BrC10=281.53)]]> Sub3-27 <![CDATA[m / z=295.91(C 12 H 6 BrClS=297.59)]]> Sub3-28 <![CDATA[m / z=371.94(C 18 H 10 BrClS=373.69)]]> Sub3-29 <![CDATA[m / z=371.94(C 18 H 10 BrClS=373.69)]]> Sub3-30 <![CDATA[m / z=279.93(C 12 H 6 BrC10=281.53)]]>

[0239] Synthesis example of final product

[0240] Synthesis Example of 1.2-15

[0241]

[0242] (1) Synthesis Example of Inter2-15

[0243] Sub3-13 (10.0 g, 28.0 mmol) was dissolved in toluene (140 mL), and then Sub2-89 (7.3 g, 28.0 mmol), Pd 2 (dba) 3 (0.77 g, 0.84 mmol), P(t-Bu) 3 (0.34 g, 1.68 mmol), NaOt-Bu (5.4 g, 55.9 mmol), and stirred at 60°C. After the reaction was completed, CH 2 Cl 2 After extraction with water, the organic layer was concentrated with MgSO 4 After drying, the concentrate was concentrated, and then the concentrate was separated by a silica gel column and recrystallized to obtain 11.5 g (yield: 77%) of a product.

[0244] (2)2-15 synthesis example

[0245] Inter2-15 (11.5 g, 21.5 mmol) was dissolved in toluene (108 mL), and Sub2-1 (3.6 g, 21.5 mmol), Pd 2 (dba) 3 (0.59 g, 0.65 mmol), P(t-Bu) 3 (0.26 g, 1.29 mmol), NaOt-Bu (4.1 g, 43.1 mmol), and stirred at 80 °C. After the reaction was completed, CH 2 Cl 2 After extraction with water, the organic layer was concentrated with MgSO 4 After drying, the concentrate was concentrated, and then the concentrate was separated by a silica gel column and recrystallized to obtain 10.1 g (yield: 70%) of a product.

[0246] Synthesis Example of 2.2-22

[0247]

[0248] (1) Synthesis Example of Inter2-22

[0249] Sub3-18 (10.0 g, 26.8 mmol) was dissolved in toluene (134 mL), and then Sub2-63 (7.4 g, 26.8 mmol), Pd 2 (dba) 3 (0.74 g, 0.80 mmol), P(t-Bu) 3(0.32 g, 1.61 mmol) and NaOt-Bu (5.1 g, 53.5 mmol) were added and purified after the reaction in the same manner as the synthesis of Inter2-15 to obtain 10.9 g of a product (yield: 72%).

[0250] (2) Synthesis Example of 2-22

[0251] Inter2-22 (10.9 g, 19.3 mmol) was dissolved in toluene (96 mL), and Sub2-1 (3.3 g, 19.3 mmol), Pd 2 (dba) 3 (0.53 g, 0.58 mmol), P(t-Bu) 3 (0.23 g, 1.16 mmol) and NaOt-Bu (3.7 g, 38.5 mmol) were added and purified after the reaction in the same manner as in the synthesis of 2-15 to obtain 10.8 g of a product (yield: 80%).

[0252] Synthesis Example of 3.2-33

[0253]

[0254] (1) Synthesis of Inter2-33

[0255] Sub3-30 (10.0 g, 35.5 mmol) was dissolved in toluene (178 mL), and then Sub2-30 (12.8 g, 35.5 mmol), Pd 2 (dba) 3 (0.98 g, 1.07 mmol), P(t-Bu) 3 (0.43 g, 2.13 mmol) and NaOt-Bu (6.8 g, 71.0 mmol) were added and purified after the reaction in the same manner as the synthesis of Inter2-15 to obtain 14.6 g of a product (yield: 73%).

[0256] (2) Synthesis of 2-33

[0257] Inter2-33 (14.6 g, 25.9 mmol) was dissolved in toluene (130 mL), and Sub2-1 (4.4 g, 25.9 mmol), Pd 2 (dba) 3 (0.71 g, 0.78 mmol), P(t-Bu) 3(0.31 g, 1.56 mmol) and NaOt-Bu (5.0 g, 51.9 mmol) were added and purified after the reaction in the same manner as in the synthesis of 2-15 to obtain 12.8 g of a product (yield: 71%).

[0258] The FD-MS values ​​of the compounds 2-1 to 2-36 of the present invention prepared according to the above-mentioned Synthesis Examples are shown in Table 5 below.

[0259] [Table 5]

[0260] Compound FD-MS Compound FD-MS 2-1 <![CDATA[m / z=624.17(C 42 H 28 N 2 S 2 =624.82)]]> 2-2 <![CDATA[m / z=654.27(C 48 H 34 N 2 0=654.81)]]> 2-3 <![CDATA[m / z=700.2(C 48 H 32 N 2 S 2 =700.92)]]> 2-4 <![CDATA[m / z=734.24(C 52 H 34 N 2 OS=734.92)]]> 2-5 <![CDATA[m / z=698.2(C 48 H 30 N 2 O 2 S=698.84)]]> 2-6 <![CDATA[m / z=635.2(C 43 H 29 N 3 OS=635.79)]]> 2-7 <![CDATA[m / z=602.24(C 44 H 30 N 2 O=602.74)]]> 2-8 <![CDATA[m / z=822.31(C 60 H 42 N 2 S=823.07)]]> 2-9 <![CDATA[m / z=670.24(C 48 H 34 N 2 S=670.87)]]> 2-10 <![CDATA[m / z=784.25(C 56 H 36 N 2 OS=784.98)]]> 2-11 <![CDATA[m / z=734.28(C 53 H 38 N 2 S=734.96)]]> 2-12 <![CDATA[m / z=905.34(C 67 H 43 N 3 O=906.1)]]> 2-13 <![CDATA[m / z=743.29(C 54 H 37 N 3 O=743.91)]]> 2-14 <![CDATA[m / z=836.32(C 61 H 44 N 2 S=837.1)]]> 2-15 <![CDATA[m / z=668.25(C 48 H 32 N 2 O 2 =668.8)]]> 2-16 <![CDATA[m / z=684.26(C 49 H 36 N 2 S=684.9)]]> 2-17 <![CDATA[m / z=618.21(C 44 H 30 N 2 S=618.8)]]> 2-18 <![CDATA[m / z=704.28(C 52 H 36 N 2 O=704.87)]]> 2-19 <![CDATA[m / z=826.25(C 58 H 38 N 2 S 2 =827.08)]]> 2-20 <![CDATA[m / z=672.38(C 48 H 16 D 18 N 2 O=672.92)]]> 2-21 <![CDATA[m / z=608.19(C 42 H 28 N 2 OS=608.76)]]> 2-22 <![CDATA[m / z=700.2(C 48 H 32 N 2 S 2 =700.92)]]> 2-23 <![CDATA[m / z=668.25(C 48 H 2 N 2 O 2 =668.8)]]> 2-24 <![CDATA[m / z=784.25(C 56 H 36 N 2 OS=784.98)]]> 2-25 <![CDATA[m / z=624.17(C 42 H 28 N 2 S 2 =624.82)]]> 2-26 <![CDATA[m / z=628.25(C 46 H 32 N 2 O=628.78)]]> 2-27 <![CDATA[m / z=694.24(C 50 H 34 N 2 S=694.9)]]> 2-28 <![CDATA[m / z=760.25(C 54 H 36 N 2 OS=760.96)]]> 2-29 <![CDATA[m / z=694.3(C 51 H 38 N 2 O=694.88)]]> 2-30 <![CDATA[m / z=730.16(C 48 H 30 N 2 S 3 =730.96)]]> 2-31 <![CDATA[m / z=592.22(C 42 H 28 N 2 O 2 =592.7)]]> 2-32 <![CDATA[m / z=750.22(C 52 H 34 N 2 S 2 =750.98)]]> 2-33 <![CDATA[m / z=694.3(C 51 H 38 N 2 O=694.88)]]> 2-34 <![CDATA[m / z=684.22(C 48 H 32 N 2 OS=684.86)]]> 2-35 <![CDATA[m / z=684.22(C 48 H 32 N 2 OS=684.86)]]> 2-36 <![CDATA[m / z=602.24(C 44 H 30 N 2 O=602.74)]]>

[0261] [Synthesis Example 3] Synthesis Example of Chemical Formula 3

[0262] The compound represented by Chemical Formula 3 according to the present invention (final product 3) is synthesized as shown in the following Reaction Formula 4, but is not limited thereto.

[0263] <Reaction 4>

[0264]

[0265] Example compounds of Sub4

[0266] The compounds belonging to Sub4 may be the same compounds as the following compounds, but are not limited thereto. The FD-MS values ​​of the following compounds are shown in Table 6.

[0267]

[0268]

[0269] [Table 6]

[0270] Compound FD-MS Compound FD-MS Sub4-1 <![CDATA[m / z=330.18(C 22 H 233 BO 2 =330.23)]]> Sub4-2 <![CDATA[m / z=380.19(C 26 H 25 BO 2 =380.29)]]> Sub4-3 <![CDATA[m / z=380.19(C 26 H 25 BO 2 =380.29)]]> Sub4-4 <![CDATA[m / z=406.21(C 28 H 27 BO 2 =406.33)]]> Sub4-5 <![CDATA[m / z=406.21(C 28 H 27 BO 2 =406.33)]]> Sub4-6 <![CDATA[m / z=482.24(C 34 H 31 BO 2 =482.43)]]> Sub4-7 <![CDATA[m / z=456.23(C 32 H 29 BO 2 =456.39)]]> Sub4-8 <![CDATA[m / z=456.23(C 32 H 29 BO 2 =456.39)]]> Sub4-9 <![CDATA[m / z=482.24(C 34 H 31 BO 2 =482.43)]]> Sub4-10 <![CDATA[m / z=430.21(C 30 H 27 BO 2 =430.35)]]> Sub4-11 <![CDATA[m / z=482.24(C 34 H 31 BO 2 =482.43)]]> Sub4-12 <![CDATA[m / z=344.19(C 23 H 25 BO 2 (=344.26)<!-- 58 --> ]]> Sub4-13 <![CDATA[m / z=344.19(C 23 H 25 BO 2 =344.26)]]> Sub4-14 <![CDATA[m / z=335.21(C 22 H 18 D 5 BO 2 =335.26)]]> Sub4-15 <![CDATA[m / z=462.26(C 32 H 23 D 6 BO 2 =462.43)]]> Sub4-16 <![CDATA[m / z=456.23(C 32 H 29 BO 2 =456.39)]]> Sub4-17 <![CDATA[m / z=341.25(C 22 H 12 D 11 BO 2 =341.3)]]> Sub4-18 <![CDATA[m / z=456.23(C 32 H 29 BO 2 =456.39)]]> Sub4-19 <![CDATA[m / z=456.23(C 32 H 29 BO 2 =456.39)]]> Sub4-20 <![CDATA[m / z=332.19(C 22 H 21 D 2 BO 2 =332.25)]]> Sub4-21 <![CDATA[m / z=456.23(C 32 H 29 BO 2 =456.39)]]> Sub422 <![CDATA[m / z=456.23(C 32 H 29 BO 2 =456.39)]]> Sub4-23 <![CDATA[m / z=482.24(C 34 H 31 BO 2 =482.43)]]> Sub4-24 <![CDATA[m / z=406.21(C 28 H 27 BO 2 =406.33)]]> Sub4-25 <![CDATA[m / z=506.24(C 36 H 31 BO 2 =506.45)]]> Sub4-26 <![CDATA[m / z=506.24(C 36 H 31 BO 2 =506.45)]]> Sub4-27 <![CDATA[m / z=456.23(C 32 H 29 BO 2 =456.39)]]> Sub4-28 <![CDATA[m / z=506.24(C 36 H 31 BO 2 =506.45)]]> Sub4-29 <![CDATA[m / z=506.24(C 36 H 31 BO 2 =506.45)]]> Sub4-30 <![CDATA[m / z=506.24(C 36 H 31 BO 2 =506.45)]]> Sub4-31 <![CDATA[m / z=506.24(C 36 H 31 BO 2 =506.45)]]> Sub4-32 <![CDATA[m / z=482.24(C 34 H 31 BO 2 =482.43)]]> Sub4-33 <![CDATA[m / z=482.24(C 34 H 31 BO 3 =482.43)]]> Sub4-34 <![CDATA[m / z=331.19(C 22 H 22 DBO 2 =331.24)]]> Sub4-35 <![CDATA[m / z=412.26(C 28 H 33 BO 2 =412.38)]]> Sub4-36 <![CDATA[m / z=456.23(C 32 H 29 BO 2 =456.39)]]> Sub4-37 <![CDATA[m / z=406.21(C 28 H 27 BO 2 =406.33)]]> Sub4-38 <![CDATA[m / z=430.21(C 30 H 27 BO 2 =430.35)]]> Sub4-39 <![CDATA[m / z=506.24(C 36 H 31 BO 2 =506.45)]]> Sub4-40 <![CDATA[m / z=482.24(C 34 H 31 B3O 2 =482.43)]]> Sub4-41 <![CDATA[m / z=506.24(C 36 H 31 BO 2 =506.45)]]> Sub4-42 <![CDATA[m / z=406.21(C 28 H 27 BO 2 =406.33)]]>

[0271] Example compounds of Sub5

[0272]

[0273] The compounds belonging to Sub5 may be the same compounds as the following compounds, but are not limited thereto. The FD-MS values ​​of the following compounds are shown in Table 7.

[0274]

[0275] [Table 7]

[0276] Compound FD-MS Compound FD-MS Sub5-1 <![CDATA[m / z=267.06(C 15 H 10 ClN 3 =267.72)]]> Sub5-2 <![CDATA[m / z=271.08(C 15 H 6 D 4 ClN 3 =271.74)]]> Sub5-3 <![CDATA[m / z=379.18(C 23 H 26 ClN 3 =379.93)]]> Sub5-4 <![CDATA[m / z=343.09(C 21 H 14 ClN 3 =343.81)]]> Sub5-5 <![CDATA[m / z=343.09(C 21 H 14 ClN 3 =343.81)]]> Sub5-6 <![CDATA[m / z=343.09(C 21 H 14 ClN 3 =343.81)]]> Sub5-7 <![CDATA[m / z=419.12(C 27 H 18 ClN 3 =419.91)]]> Sub5-8 <![CDATA[m / z=429.18(C 27 H 8 D 10 ClN 3 =429.97)]]> Sub5-9 <![CDATA[m / z=419.12(C 27 H 18 ClN 3 =419.91)]]> Sub5-10 <![CDATA[m / z=419.12(C 27 H 18 ClN 3 =419.91)]]> Sub5-11 <![CDATA[m / z=317.07(C 19 H 12 ClN 3 (=317.78)]]> Sub5-12 <![CDATA[m / z=322.1(C 19 H 7 D 5 ClN 3 =322.81)]]> Sub5-13 <![CDATA[m / z=393.1(C 25 H 16 ClN 3 =393.87)]]> Sub5-14 <![CDATA[m / z=317.07(C 19 H 12 ClN 3 (=317.78)]]> Sub5-15 <![CDATA[m / z=393.1(C 25 H 16 ClN 3 =393.87)]]> Sub5-16 <![CDATA[m / z=393.1(C 25 H 16 ClN 3 =393.87)]]> Sub5-17 <![CDATA[m / z=367.09(C 23 H 14 ClN 3 (=367.84)]]> Sub5-18 <![CDATA[m / z=443.12(C 29 H 18 ClN 3 =443.93)]]> Sub5-19 <![CDATA[m / z=367.09(C 23 H 14 ClN 3 (=367.84)]]> Sub5-20 <![CDATA[m / z=367.09(C 23 H 14 ClN 3 (=367.84)]]> Sub5-21 <![CDATA[m / z=443.12(C 29 H 18 ClN 3 =443.93)]]> Sub5-22 <![CDATA[m / z=524.18(C 35 H 17 F 5 ClN 3 =525.06)]]> Sub5-23 <![CDATA[m / z=393.1(C 25 H 16 ClN 3 =393.87)]]> Sub5-24 <![CDATA[m / z=469.13(C 31 H 20 ClN 3 =469.97)]]> Sub5-25 <![CDATA[m / z=367.09(C 23 H 14 ClN 3 (=367.84)]]> Sub5-26 <![CDATA[m / z=443.12(C 29 H 18 ClN 3 =443.93)]]> Sub5-27 <![CDATA[m / z=367.09(C 23 H 14 ClN 3 (=367.84)]]> Sub5-28 <![CDATA[m / z=367.09(C 23 H 14 ClN 3 (=367.84)]]> Sub5-29 <![CDATA[m / z=417.1(C 27 H 16 ClN 3 =417.9)]]> Sub5-30 <![CDATA[m / z=419.12(C 27 H 18 ClN 3 =419.91)]]> Sub5-31 <![CDATA[m / z=419.12(C 27 H 18 ClN 3 =419.91)]]> Sub5-32 <![CDATA[m / z=419.12(C 27 H 18 ClN 3 =419.91)]]> Sub5-33 <![CDATA[m / z=419.12(C 27 H 18 ClN 3 =419.91)]]> Sub5-34 <![CDATA[m / z=393.1(C 25 H 16 ClN 3 =393.87)]]> Sub5-35 <![CDATA[m / z=469.13(C 31 H 20 ClN 3 =469.97)]]> Sub5-36 <![CDATA[m / z=519.15(C 35 H 22 ClN 3 =520.03)]]> Sub5-37 <![CDATA[m / z=303.04(C 15 H 8 ClF 2 N 3 =303.7)]]> Sub5-38 <![CDATA[m / z=368.08(C 22 H 13 ClN 4 =368.82)]]> Sub5-39 <![CDATA[m / z=368.08(C 22 H 13 ClN 4 =368.82)]]> Sub5-40 <![CDATA[m / z=383.12(C 24 H 18 ClN 3 =383.88)]]>

[0277] Synthesis Example of Final Product 1. Synthesis Example of N-7

[0278]

[0279] Sub4-1 (10.0 g, 30.3 mmol) was dissolved in THF (Tetrahydrofuran) (151 mL), and then Sub5-20 (11.1 g, 30.3 mmol), NaOH (3.6 g, 90.8 mmol), Pd (PPh 3 ) 4 (2.10 g, 1.82 mmol) and water (76 mL) and stirred at 80 °C. After the reaction was completed, CH 2 Cl 2 After extraction with water, the organic layer was concentrated with MgSO 4 After drying, the concentrate was concentrated, and then separated by a silica gel column and recrystallized to obtain 13.3 g (yield: 82%) of a product.

[0280] 2. Synthesis Example of N-38

[0281]

[0282] Sub4-21 (10.0 g, 21.9 mmol) was dissolved in THF (110 mL), and then Sub5-1 (5.9 g, 21.9 mmol), NaOH (2.6 g, 65.7 mmol), Pd(PPh 3 ) 4 (1.52 g, 1.31 mmol) and water (55 mL) were added and purified after the reaction in the same manner as the synthesis of N-7 to obtain 9.6 g of a product (yield: 78%).

[0283] 3. Synthesis example of N-65

[0284]

[0285] Sub4-40 (10.0 g, 20.7 mmol) was dissolved in THF (104 mL), and Sub5-1 (5.5 g, 20.7 mmol), NaOH (2.5 g, 62.2 mmol), Pd(PPh 3 ) 4 (1.44 g, 1.24 mmol) and water (52 mL) were added and purified after the reaction in the same manner as the synthesis of N-7 to obtain 9.1 g of a product (yield: 75%).

[0286] The FD-MS values ​​of the compounds N-1 to N-68 of the present invention prepared according to the above-mentioned Synthesis Examples are shown in Table 8 below.

[0287] [Table 8]

[0288]

[0289]

[0290] [Synthesis Example 4] Synthesis Example of Chemical Formula 4

[0291] The compound represented by Chemical Formula 4 according to the present invention (final product 4) is synthesized as shown in the following Reaction Formula 5, but is not limited thereto.

[0292] <Reaction 5>

[0293]

[0294] Example compounds of Sub6

[0295] The compounds belonging to Sub6 may be the same compounds as the following compounds, but are not limited thereto. The FD-MS values ​​of the following compounds are shown in Table 9.

[0296]

[0297]

[0298] [Table 9]

[0299] Compound FD-MS Compound FD-MS Sub6-1 <![CDATA[m / z=458.18(C 34 H 22 N 2 =458.56)]]> Sub6-2 <![CDATA[m / z=508.19(C 38 H 24 N 2 =508.62)]]> Sub6-3 <![CDATA[m / z=382.15(C 28 H 18 N 2 =382.47)]]> Sub6-4 <![CDATA[m / z=432.16(C 32 H 20 N 2 =432.53)]]> Sub6-5 <![CDATA[m / z=382.15(C 28 H 18 N 2 =382.47)]]> Sub6-6 <![CDATA[m / z=458.18(C 34 H 22 N 2 =458.56)]]> Sub6-7 <![CDATA[m / z=458.18(C 34 H 22 N 2 =458.56)]]> Sub6-8 <![CDATA[m / z=558.21(C 42 H 26 N 2 =558.68)]]> Sub6-9 <![CDATA[m / z=458.18(C 34 H 22 N 2 =458.56)]]> Sub6-10 <![CDATA[m / z=432.16(C 32 H 20 N 2 =432.53)]]> Sub6-11 <![CDATA[m / z=382.15(C 28 H 18 N 2 =382.47)]]> Sub6-12 <![CDATA[m / z=432.16(C 32 H 20 N 2 =432.53)]]> Sub6-13 <![CDATA[m / z=508.19(C 38 H 24 N 2 =508.62)]]> Sub6-14 <![CDATA[m / z=482.18(C 36 H 22 N 2 =482.59)]]> Sub6-15 <![CDATA[m / z=382.15(C 28 H 18 N 2 =382.47)]]> Sub6-16 <![CDATA[m / z=382.15(C 28 H 18 N 2 =382.47)]]> Sub6-17 <![CDATA[m / z=508.19(C 38 H 24 N 2 =508.62)]]> Sub6-18 <![CDATA[m / z=458.18(C 34 H 22 N 2 =458.56)]]> Sub6-19 <![CDATA[m / z=458.18(C 34 H 22 N 2 =458.56)]]> Sub6-20 <![CDATA[m / z=382.15(C 28 H 18 N 2 =382.47)]]> Sub6-21 <![CDATA[m / z=432.16(C 32 H 20 N 2 =432.53)]]> Sub6-22 <![CDATA[m / z=382.15(C 28 H 18 N 2 =382.47)]]> Sub6-23 <![CDATA[m / z=382.15(C 28 H 18 N 2 =382.47)]]> Sub6-24 <![CDATA[m / z=458.18(C 34 H 22 N 2 =458.56)]]> Sub6-25 <![CDATA[m / z=432.16(C 32 H 20 N 2 =432.53)]]> Sub6-26 <![CDATA[m / z=382.15(C 28 H 18 N 2 =382.47)]]> Sub6-27 <![CDATA[m / z=458.18(C 34 H 22 N 2 =458.56)]]> Sub6-28 <![CDATA[m / z=508.19(C 38 H 24 N 2 =508.62)]]> Sub6-29 <![CDATA[m / z=382.15(C 28 H 18 N 2 =382.47)]]> Sub6-30 <![CDATA[m / z=382.15(C 28 H 18 N 2 =382.47)]]> Sub6-31 <![CDATA[m / z=438.21(C 32 H 26 N 2 =438.57)]]> Sub6-32 <![CDATA[m / z=458.18(C 34 H 22 N 2 =458.56)]]> Sub6-33 <![CDATA[m / z=432.16(C 32 H 20 N 2 =432.53)]]> Sub6-34 <![CDATA[m / z=382.15(C 28 H 18 N 2 =382.47)]]> Sub6-35 <![CDATA[m / z=382.15(C 28 H 18 N 2 =382.47)]]> Sub6-36 <![CDATA[m / z=458.18(C 34 H 22 N 2 =458.56)]]> Sub6-37 <![CDATA[m / z=432.16(C 32 H 20 N 2 =432.53)]]> Sub6-38 <![CDATA[m / z=382.15(C 28 H 18 N 2 =382.47)]]> Sub6-39 <![CDATA[m / z=382.15(C 28 H 18 N 2 =382.47)]]> Sub6-40 <![CDATA[m / z=468.22(C 33 H 28 N 2 O=468.6)]]> Sub6-41 <![CDATA[m / z=382.15(C 28 H 18 N 2 =382.47)]]> Sub6-42 <![CDATA[m / z=458.18(C 34 H 22 N 2 =458.56)]]> Sub6-43 <![CDATA[m / z=458.18(C 34 H 22 N 2 =458.56)]]> Sub6-44 <![CDATA[m / z=382.15(C 28 H 18 N 2 =382.47)]]> Sub6-45 <![CDATA[m / z=382.15(C 28 H 18 N 2 =382.47)]]> Sub6-46 <![CDATA[m / z=508.19(C 38 H 24 N 2 =508.62)]]> Sub6-47 <![CDATA[m / z=458.18(C 34 H 22 N 2 =458.56)]]> Sub6-48 <![CDATA[m / z=432.16(C 32 H 20 N 2 =432.53)]]> Sub6-49 <![CDATA[m / z=534.21(C 40 H 26 N 2 =534.66)]]> Sub6-50 <![CDATA[m / z=382.15(C 28 H 18 N2=382.47)]]> Sub6-51 <![CDATA[m / z=432.16(C 32 H 20 N 2 =432.53)]]> Sub6-52 <![CDATA[m / z=458.18(C 34 H 22 N 2 =458.56)]]> Sub6-53 <![CDATA[m / z=382.15(C 28 H 18 N 2 =382.47)]]> Sub6-54 <![CDATA[m / z=458.18(C 34 H 22 N 2 =458.56)]]> Sub6-55 <![CDATA[m / z=534.21(C 40 H 26 N 2 =534.66)]]> Sub6-56 <![CDATA[m / z=432.16(C 32 H 20 N 2 =432.53)]]> Sub6-57 <![CDATA[m / z=382.15(C 28 H 18 N 2 =382.47)]]> Sub6-58 <![CDATA[m / z=458.18(C 34 H 22 N 2 =458.56)]]> Sub6-59 <![CDATA[m / z=508.19(C 38 H 24 N 2 =508.62)]]>

[0300] Synthesis example of final product

[0301] 1. Synthesis example of P-10

[0302]

[0303] Sub6-9 (10.0 g, 21.8 mmol) was dissolved in toluene (109 mL), and Sub1-8 (5.1 g, 21.8 mmol), Pd 2 (dba) 3 (0.60 g, 0.65 mmol), P(t-Bu) 3 (0.26 g, 1.31 mmol), NaOt-Bu (4.2 g, 43.6 mmol), and stirred at 80 °C. After the reaction was completed, CH 2 Cl 2 After extraction with water, the organic layer was concentrated with MgSO 4 After drying, the concentrate was concentrated, and then separated by a silica gel column and recrystallized to obtain 10.3 g (yield: 77%) of a product.

[0304] 2. Synthesis example of P-20

[0305]

[0306] Sub6-17 (10.0 g, 19.7 mmol) was dissolved in toluene (98 mL), and Sub1-2 (3.2 g, 19.7 mmol), Pd 2 (dba) 3 (0.54 g, 0.59 mmol), P(t-Bu) 3 (0.24 g, 1.18 mmol) and NaOt-Bu (3.8 g, 39.3 mmol) were added and purified after the reaction in the same manner as the synthesis of P-10 to obtain 9.4 g of a product (yield: 81%).

[0307] 3. Synthesis Example of P-61

[0308]

[0309] Sub6-50 (10.0 g, 26.1 mmol) was dissolved in toluene (131 mL), and Sub1-88 (7.8 g, 26.1 mmol), Pd 2 (dba) 3 (0.72 g, 0.78 mmol), P(t-Bu) 3 (0.32 g, 1.57 mmol) and NaOt-Bu (5.0 g, 52.3 mmol) were added and purified after the reaction in the same manner as the synthesis of P-10 to obtain 11.9 g of a product (yield: 76%).

[0310] The FD-MS values ​​of the compounds P-1 to P-72 of the present invention prepared according to the above-mentioned Synthesis Examples are shown in Table 10 below.

[0311] [Table 10]

[0312]

[0313]

[0314] [Synthesis Example 5] Synthesis Example of Chemical Formula 6

[0315] The compound represented by Chemical Formula 6 according to the present invention (final product 6) is synthesized as shown in the following Reaction Formula 6, but is not limited thereto.

[0316] <Reaction formula 6>

[0317]

[0318] Example compounds of Sub7

[0319] The compounds belonging to Sub7 may be the same compounds as the following compounds, but are not limited thereto. The FD-MS values ​​of the following compounds are shown in Table 11.

[0320]

[0321]

[0322] [Table 11]

[0323] Compound FD-MS Compound FD-MS Sub7-1 <![CDATA[m / z=280.16(C 18 H 21 BO 2 =280.17)]]> Sub7-2 <![CDATA[m / z=356.19(C 24 H 25 BO 2 =356.27)]]> Sub7-3 <![CDATA[m / z=330.18(C 22 H 23 BO 2 =330.23)]]> Sub7-4 <![CDATA[m / z=406.21(C 28 H 27 BO 2 =406.33)]]> Sub7-5 <![CDATA[m / z=507.24(C 35 H 30 B.N.O. 2 =507.44)]]> Sub7-6 <![CDATA[m / z=485.25(C 33 H 32 B.N.O. 2 =485.43)]]> Sub7-7 <![CDATA[m / z=483.24(C 33 HH 30 BN0 2 =483.42)]]> Sub7-8 <![CDATA[m / z=472.26(C 33 H.H. 33 BO 2 =472.44)]]> Sub7-9 <![CDATA[m / z=442.21(C 31 H 27 BO 2 =442.37)]]> Sub7-10 <![CDATA[m / z=396.23(C 27 H 29 BO 2 =396.34)]]> Sub7-11 <![CDATA[m / z=444.23(C 31 H 29 BO 2 =444.38)]]> Sub7-12 <![CDATA[m / z=294.14(C 18 H 19 BO 3 =294.16)]]> Sub7-13 <![CDATA[m / z=370.17(C 24 H 23 BO 3 =370.26)]]> Sub7-14 <![CDATA[m / z=386.15(C 24 H 23 B.O. 2 S=386.32)]]> Sub7-15 <![CDATA[m / z=310.12(C 18 H 19 B.O. 2 S=310.22)]]> Sub7-16 <![CDATA[m / z=369.19(C 24 H 24 B.N.O. 2 =369.27)]]> Sub7-17 <![CDATA[m / z=445.22(C 30 H 28 B.N.O. 2 =445.37)]]> Sub7-18 <![CDATA[m / z=445.22(C 30 H 28 B.N.O. 2 =445.37)]]> Sub7-19 <![CDATA[m / z=445.22(C 30 H 28 BN0 2 =445.37)]]> Sub7-20 <![CDATA[m / z=460.23(C 30 H 29 BN 2 0 2 =460.38)]]> Sub7-21 <![CDATA[m / z=536.26(C 36 A 33 BN 2 O 2 =536.48)]]> Sub7-22 <![CDATA[m / z=514.3(C 36 H 39 BO 2 =514.52)]]> Sub7-23 <![CDATA[m / z=484.26(C 34 H 33 BO 2 =484.45)]]> Sub7-24 <![CDATA[m / z=386.17(C 24 H 23 BO 4 =386.25)]]> Sub7-25 <![CDATA[m / z=402.15(C 24 H 23 B.O. 3 S=402.32)]]> Sub7-26 <![CDATA[m / z=461.22(C 30 H 28 B.N.O. 3 =461.37)]]> Sub7-27 <![CDATA[m / z=477.19(C 30 H 28 BNO 2 S=477.43)]]> Sub7-28 <![CDATA[m / z=411.24(C 27 H 30 B.N.O. 2 =411.35)]]> Sub7-29 <![CDATA[m / z=411.24(C 27 H 30 B.N.O. 2 =411.35)]]> Sub7-30 <![CDATA[m / z=392.25(C 25 H 33 BO 3 =392.35)]]> Sub7-31 <![CDATA[m / z=402.18(C 25 H 27 B.O. 2 S=402.36)]]> Sub7-32 <![CDATA[m / z=533.25(C 37 H 32 B.N.O. 2 =533.48)]]> Sub7-33 <![CDATA[m / z=609.28(C 43 H 36 B.N.O. 2 =609.58)]]> Sub7-34 <![CDATA[m / z=458.21(C 31 H 27 BO 3 =458.36)]]> Sub7-35 <![CDATA[m / z=458.21(C 31 H 27 BO 3 =458.36)]]>

[0324] Synthesis example of final product

[0325] Synthesis Example of 1.6-7

[0326]

[0327] Sub7-6 (10.0 g, 20.6 mmol) was dissolved in THF (Tetrahydrofuran) (103 mL), and then Sub5-1 (5.5 g, 20.6 mmol), NaOH (2.5 g, 61.8 mmol), Pd (PPh 3 ) 4 (1.43 g, 1.24 mmol) and water (52 mL) and stirred at 80 °C. After the reaction was completed, CH 2 Cl 2 After extraction with water, the organic layer was concentrated with MgSO 4 After drying, the concentrate was concentrated, and then separated by a silica gel column and recrystallized to obtain 9.4 g (yield: 77%) of a product.

[0328] Synthesis Example of 2.6-9

[0329]

[0330] Sub7-8 (10.0 g, 21.2 mmol) was dissolved in THF (106 mL), and Sub5-1 (5.7 g, 21.2 mmol), NaOH (2.5 g, 63.5 mmol), Pd(PPh 3 ) 4 (1.47 g, 1.27 mmol) and water (53 mL) were added and purified after the reaction in the same manner as in the synthesis of 6-7 to obtain 9.5 g of a product (yield: 78%).

[0331] Synthesis Example of 3.6-35

[0332]

[0333] Sub7-34 (10.0 g, 21.8 mmol) was dissolved in THF (110 mL), and then Sub5-39 (8.0 g, 21.8 mmol), NaOH (2.6 g, 65.5 mmol), Pd(PPh 3 ) 4 (1.15 g, 1.31 mmol) and water (55 mL) were added and the reaction was purified in the same manner as in the synthesis of 6-7 to obtain 10.4 g of a product (yield: 72%).

[0334] The FD-MS values ​​of the compounds 6-1 to 6-36 of the present invention prepared according to the above-mentioned Synthesis Examples are shown in Table 12 below.

[0335] [Table 12]

[0336] Compound FD-MS Compound FD-MS 6-1 <![CDATA[m / z=537.22(C 39 H 27 N 3 =537.67)]]> 6-2 <![CDATA[m / z=511.2(C 37 H 25 N 3 =511.63)]]> 6-3 <![CDATA[m / z=587.24(C 43 H 29 N 3 =587.73)]]> 6-4 <![CDATA[m / z=612.23(C 44 H 28 N 4 =612.74)]]> 6-5 <![CDATA[m / z=613.25(C 45 H 31 N 3 =613.76)]]> 6-6 <![CDATA[m / z=587.24(C 43 H 29 N 3 =587.73)]]> 6-7 <![CDATA[m / z=590.25(C 42 H 30 N 4 =590.73)]]> 6-8 <![CDATA[m / z=588.23(C 42 H 28 N 4 =588.71)]]> 6-9 <![CDATA[m / z=577.25(C 42 H 31 N 3 =577.73)]]> 6-10 <![CDATA[m / z=623.24(C 46 H 29 N 3 =623.76) <!-- 73 -->]]> 6-11 <![CDATA[m / z=577.25(C 42 H 31 N 3 =577.73)]]> 6-12 <![CDATA[m / z=625.25(C 46 H 31 N 3 =625.78)]]> 6-13 <![CDATA[m / z=601.22(C 43 H 27 N 3 O=601.71)]]> 6-14 <![CDATA[m / z=627.23(C 45 H 29 N 3 O=627.75)]]> 6-15 <![CDATA[m / z=591.18(C 41 H 25 N 3 S=591.73)]]> 6-16 <![CDATA[m / z=667.21(C 47 H 29 N 3 S=667.83)]]> 6-17 <![CDATA[m / z=626.25(C 45 H 30 N 4 =626.76)]]> 6-18 <![CDATA[m / z=626.25(C 45 H 30 N 4 =626.76)]]> 6-19 <![CDATA[m / z=702.28(C 51 H 34 N 4 =702.86)]]> 6-20 <![CDATA[m / z=702.28(C 51 H 34 N 4 =702.86)]]> 6-21 <![CDATA[m / z=681.29(C 48 H 35 N 5 =681.84)]]> 6-22 <![CDATA[m / z=641.26(C 45 H 31 N 5 =641.78)]]> 6-23 <![CDATA[m / z=619.3(C 45 H 37 N 3 =619.81)]]> 6-24 <![CDATA[m / z=589.25(C 43 H 31 N 3 =589.74)]]> 6-25 <![CDATA[m / z=541.18(C 37 H 23 N 3 O 2 =541.61)]]> 6-26 <![CDATA[m / z=507.14(C 33 H 21 N 3 OS=507.61)]]> 6-27 <![CDATA[m / z=616.23(C 43 H 28 N 4 O=616.72)]]> 6-28 <![CDATA[m / z=658.22(C 45 H 30 N 4 S=658.82)]]> 6-29 <![CDATA[m / z=642.28(C 46 H 34 N 4 =642.81)]]> 6-30 <![CDATA[m / z=592.26(C 42 H 32 N 4 =592.75)]]> 6-31 <![CDATA[m / z=533.23(C 34 H 29 F 2 N 3 O=533.62)]]> 6-32 <![CDATA[m / z=608.2(C 41 H 28 N 4 S=608.76)]]> 6-33 <![CDATA[m / z=764.29(C 56 H 36 N 4 =764.93)]]> 6-34 <![CDATA[m / z=714.28(C 52 H 34 N 4 =714.87)]]> 6-35 <![CDATA[m / z=664.23(C 47 H 28 N 4 O=664.77)]]> 6-36 <![CDATA[m / z=689.25(C 50 H 31 N 3 O=689.82)]]>

[0337] Manufacturing and evaluation of organic electrical components

[0338] [Example 1] Red organic light emitting element

[0339] After a 70 nm thick hole injection layer is formed by vacuum depositing a film of 4,4',4"-tri[2-naphthyl(phenyl)amino]triphenylamine (hereinafter referred to as "2-TNATA") on the ITO layer (anode) formed on the glass substrate, a 70 nm thick film of the hole transport compound A-1 is vacuum deposited on the hole injection layer to form a hole transport layer.

[0340] Then, the compound 2-22 of the present invention was vacuum deposited on the hole transport layer with a thickness of 70 nm to form a first luminescence-assisting layer (P1), and the compound 1-13 of the present invention was vacuum deposited on the first luminescence-assisting layer with a thickness of 5 nm to form a second luminescence-assisting layer (P2).

[0341] Next, a mixture of a first host (H1) N-7 and a second host (H2) P-10 in a weight ratio of 5:5 was used as a host on the light-emitting auxiliary layer, and di-(1-phenylisoquinolyl) iridium (III) (acetylacetone) (hereinafter referred to as "(piq) 2 Ir(acac)") was used as a doping material and doped at a weight ratio of 95:5, and a light-emitting layer was vacuum deposited with a thickness of 40nm.

[0342] Next, C-1 was vacuum-deposited on the light-emitting layer to a thickness of 30 nm to form an electron transport layer.

[0343] Next, LiF was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode.

[0344] [Example 2] to [Example 40]

[0345] An organic light emitting device was prepared in the same manner as in Example 1 except that the compounds listed in Table 13 were used as materials for the hole transport layer, the first light emitting auxiliary layer, the second light emitting auxiliary layer, the electron transport layer and the host.

[0346] [Comparative Example 1] to [Comparative Example 3]

[0347] An organic light-emitting element was prepared by using the compounds listed in Table 13 as materials for the hole transport layer, electron transport layer and host in the same manner as in Example 1. The difference from Example 1 is that no light-emitting auxiliary layer was formed and a single material was used as the host.

[0348] [Comparative Example 4]

[0349] An organic light emitting device was prepared by using the compounds listed in Table 13 below as materials for the hole transport layer, electron transport layer and host in the same manner as in Example 1. The difference from Example 1 is that no light emitting auxiliary layer was formed.

[0350] [Comparative Example 5]

[0351] An organic light-emitting element was prepared by using the compounds listed in Table 13 below as materials for the hole transport layer, the light-emitting auxiliary layer, the electron transport layer and the main body in the same manner as in Example 1. The difference from Example 1 is that the light-emitting auxiliary layer is formed as a single layer of a single material and a single material is used as the main body.

[0352] The structures of Compound A-1, Compound B-1, and Compound C-1 shown in Table 13 below are as follows.

[0353]

[0354] A forward bias DC voltage was applied to the organic light-emitting elements prepared by the above-mentioned embodiments and comparative examples, and the electroluminescence (EL) characteristics were measured using a PR-650 from Photo Research, Inc., USA. 2 In the reference brightness, the T95 life was measured by a life measuring device manufactured by MacScience Co., Ltd. The measurement results are shown in Table 13 below.

[0355] [Table 13]

[0356]

[0357]

[0358] Referring to Table 13, it can be seen that, compared with Comparative Examples 1 to 5, when the organic layer is constructed as in the present invention, the driving voltage of the organic electrical element is reduced, and the efficiency and life are significantly improved.

[0359] Observing Comparative Examples 1 to 3, when the light-emitting auxiliary layer is not formed and the hole transport layer and the electron transport layer are formed with different substances, the characteristics of the device will also be different depending on the type of the host. That is, compared with Comparative Example 1 using Compound B-1 as the host, the device characteristics of Comparative Example 2 using Compound N-7 are excellent, and compared with Comparative Example 2, the device characteristics of Comparative Example 3 using Compound P-10 as the host are even better. It can be seen that the characteristics of the device will also be different depending on the host.

[0360] Furthermore, it can be seen from the observation of Comparative Examples 1 to 4 that, without forming a light-emitting auxiliary layer, the device characteristics of Comparative Example 4 in which the host is mixed are superior to those of Comparative Examples 1 to 3 in which a single host is used.

[0361] Furthermore, it can be seen from the observation of Comparative Examples 1 and 5 that the characteristics of the element of Comparative Example 5 in which the luminescence assisting layer is formed as a single layer are more excellent than those of Comparative Example 1 in which the luminescence assisting layer is not formed.

[0362] Therefore, in order to improve the characteristics of the element, the present invention forms a luminescent auxiliary layer and mixes two substances as the main body. It can be confirmed through the examples in Table 13 that the characteristics of the element are significantly improved compared with the comparative example. In particular, by observing the comparative example 4 and the embodiment 10 of the present invention, it can be confirmed that the materials of the hole transport layer and the electron transport layer are the same. Even if the same main body is used, the characteristics of the element are significantly improved in the case of the embodiment 10 of the present invention in which the luminescent auxiliary layer is formed compared with the comparative example 4.

[0363] Like the present invention, when each layer of the organic layer is composed of a combination of specific compounds, the energy levels (HOMO, LUMO, T1 energy levels) of the compounds in each layer and the physical properties of the compounds have appropriate values ​​for improving the charge balance within the light-emitting layer. As a result, good luminescence is formed inside the light-emitting layer rather than at the interface of the light-emitting layer, and as the degradation of the interface of the light-emitting layer is reduced, the driving voltage, efficiency and life are improved.

[0364] The above description is for illustrative purposes only, and a person skilled in the art can make various modifications without departing from the essential characteristics of the present invention.

Claims

1. An organic electrical element, comprising a first electrode, a second electrode and an organic layer formed between the first electrode and the second electrode, wherein: The organic layer includes: a light-emitting layer, a hole transport layer formed between the first electrode and the light-emitting layer, and a light-emitting auxiliary layer formed between the hole transport layer and the light-emitting layer. The light-emitting auxiliary layer includes a compound represented by the following chemical formula 1, the light-emitting layer includes a compound represented by the following chemical formula 4-1, and the hole transport layer includes a compound represented by the following chemical formula 5. <Chemical Formula 5> In the above chemical formula, Ar 1 is fluorenyl, Ar 2 C6~C 18 aryl; or fluorenyl, Ar 3 C6~C 18 The aromatic group, Ar 11 and Ar 12 Independent of each other, C6~C 18 or a C2-C 16 The heterocyclic group, Ar 13 C6~C 18 aryl; or fluorenyl, Ar 14 C6~C 18 The aromatic group, L 1 To L 3 , L 10 To L 12 , L b and L c Independently of each other, they are single bonds; or C6~C 12 The arylene group, Ring B is a C6 aryl ring, and Ring B may be substituted by one or more R4 groups which are the same or different from each other. R 4 , R4, R 21 , R 30 and R 31 Independently of each other, they are hydrogen; or deuterium, d and a1 are each an integer from 0 to 4, b1 is an integer from 0 to 3, and w is an integer from 0 to 6, R e and R f Independent of each other as C1-C 10 Alkyl; or C6~C 18 The aromatic group, and R e and R f can combine with each other to form a ring, and The above aryl group, arylene group, fluorenyl group, heterocyclic group, R e and R f The rings formed by the mutual combination can be selected from deuterium, C1-C 10 Alkyl, C6-C 18 The group consisting of an aryl group and a fluorenyl group may be further substituted with one or more substituents selected from the group consisting of an aryl group and a fluorenyl group.

2. The organic electric element according to claim 1, wherein The above chemical formula 1 is represented by the following chemical formula 1-2, <Chemical Formula 1-2> In the above chemical formula 1-2, Ar 2 ,Ar 3 , L 1 To L 3 Same as defined in claim 1, Y 1 is C(R5)(R6), R5 and R6 are independent of each other and are C1-C 10 of an alkyl group, and R 7 and R 8 are independently hydrogen or deutrium, g is an integer of 0-3, and h is an integer of 0-4.

3. The organic electric element according to claim 2, wherein The above L 1 For a single key.

4. The organic electric element according to claim 3, wherein ⅰ) The above L 2 is a single bond, and Ar 2 To be able to be C1-C 10 9,9-diphenyl-9H-fluorenyl substituted with an alkyl radical, or ii) L 2 To be able to be C1-C 10 an alkyl-substituted C6 arylene group, and Ar 2 It is a fluorenyl group which may be substituted by a C6 aryl group.

5. The organic electric element according to claim 4, wherein ⅰ) L 3 is a C6 arylene group, and Ar 3 is a C6 aryl group, or ii) L 3 is a single bond, and Ar 3 It is biphenyl.

6. The organic electric element according to claim 1, wherein L b is a single bond, and Ar 11 C6~C 12 The aromatic group.

7. The organic electric element according to claim 6, wherein L c C6~C 12 The arylene group, and Ar 12 C2~C containing O 16 The heterocyclic group.

8. The organic electric element according to claim 7, wherein Ar 11 is a C6 aryl group, L c is a C6 arylene group, and Ar 12 It is dibenzofuranyl.

9. The organic electric element according to claim 1, wherein L 10 For a single key.

10. The organic electric element according to claim 9, wherein Ar 13 is 9,9-diphenyl-9H-fluorenyl, 9,9'-spirobifluorenyl, or C6~C 12 of an aromatic group, and Ar 14 C6~C 12 The aromatic group.

11. The organic electric element according to claim 10, wherein R e and R f are methyl, L 11 is a single bond, and Ar 13 is 9,9-diphenyl-9H-fluorenyl, and L 12 is a single bond or a C6 arylene group, and Ar 14 is phenyl or biphenyl.

12. The organic electric element according to claim 10, wherein R e and R f They combine with each other to form a ring, L 11 and L 12 are independently a single bond or a C6 arylene group, and Ar 13 or Ar 14 are independently phenyl or biphenyl.

13. The organic electric element according to claim 12, wherein R e and R f They combine with each other to form spiro compounds.

14. The organic electric element according to claim 12, wherein R e and R f They combine with each other to form a fluorene ring.

15. The organic electric element according to claim 1, wherein The organic layer includes an electron transport layer formed between the second electrode and the light emitting layer, and the electron transport layer includes a compound represented by the following Chemical Formula 6: <Chemical Formula 6> In the above chemical formula 6, X 1 To X 3 For N, L 13 To L 15 Independently of each other, they are single bonds; or C6~C 24 The arylene group, Ar 15 and Ar 16 Independent of each other, C6~C 18 or containing at least one heteroatom selected from O, N and S C2 ~ C 30 The heterocyclic group, Ar 17 C6~C 24 of an aromatic group, and The above-mentioned aryl and heterocyclic groups can be selected from deuterium, cyano, C6-C 30 an aryl group, a C2-C 30 The group consisting of the heterocyclic group is further substituted by one or more substituents.

16. The organic electric element according to claim 15, wherein The above Ar 15 is a C2-C 25 A heterocyclic group, and Ar 16 C6~C 12 or containing at least one heteroatom selected from O, N and S C2 ~ C 13 The heterocyclic group.

17. The organic electric element according to claim 15, wherein The above Chemical Formula 6 is represented by one of the following Chemical Formulas 6-1 to 6-3, <Chemical Formula 6-1> In the above Chemical Formulae 6-1 to 6-3, X 1 To X 3 , L 13 To L 15 ,Ar 16 ,Ar 17 Same as defined in claim 15, X 4 is O or S, X 5 O, S or C (R 21 )(R 22 ), X 6 and X 7 Independent of each other, they are O or S. R 32 To R 37 Independently of each other, they are either hydrogen or deuterium. R 21 and R 22 C1~C 10 Alkyl, or R 21 and R 22 They combine with each other to form a ring, and c1, e1, f1, g1 and h1 are integers of 0-4 respectively, and d1 is an integer of 0-3.

18. The organic electric element according to claim 17, wherein The above chemical formula 6 is the above chemical formula 6-2, X 6 is O, and L 13 is a single bond, L 14 is a single bond, and Ar 16 is phenyl, and L 15 is a single bond or a C6 arylene group, Ar 17 It is a phenyl group which may be substituted by a cyano group or a biphenyl group which may be substituted by a cyano group.

19. The organic electric element according to claim 15, wherein L 13 is a single bond, Ar 15 C containing N 13 The heterocyclic group, ⅰ) L 14 is a single bond, Ar 16 is a C6 aryl group, Ar 16 It can be a C5 heterocyclic group containing N and a C 13 or ii) L 14 is a C6 arylene group, Ar 16 is a C5 heterocyclic group containing N or a C 13 The heterocyclic group, and L 14 It may be a C5 heterocyclic group containing N or a C 13 is substituted with a heterocyclic group, and L 15 is a single bond, Ar 17 It is phenyl.

20. The organic electric element according to claim 15, wherein L 13 C6~C 22 Arylene, Ar 15 is a C3 heterocyclic group containing N, Ar 15 may be substituted with one or more C6 aryl groups, and L 14 and L 15 is a single bond, Ar 16 and Ar 17 They are phenyl.

21. The organic electric element according to claim 1, wherein The organic layer includes two or more stacks, and the stack includes a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the first electrode.

22. The organic electric element according to claim 1, wherein The above-mentioned organic electrical element is a red organic electrical light-emitting element.

23. An electronic device, wherein: include: A display device comprising the organic electric element according to claim 1; as well as The control unit is used to drive the display device.

24. The electronic device according to claim 23, wherein: The electronic device mentioned above is a wired or wireless communication terminal.

25. The electronic device according to claim 24, wherein: The above-mentioned wired or wireless communication terminals include mobile communication terminals, navigators, game consoles, TVs, and computers.

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