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

Abstract

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

Description

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

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

[0002] Generally, organic light emitting diodes (OLEDs) are devices that convert electrical energy into light energy using organic materials. Organic electronic devices utilizing the organic light emitting diode (OLED) phenomenon typically have a structure comprising an anode, a cathode, and an organic layer between them. These organic layers are often multilayered, composed of different materials, to enhance the efficiency and stability of the device. For example, these layers may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

[0003] The biggest issues with organic light-emitting diodes are their lifespan and efficiency, and as displays become larger in size, these efficiency and lifespan issues must be resolved.

[0004] Efficiency, lifespan, and operating voltage are all interrelated. As efficiency increases, the operating voltage relatively decreases. As the operating voltage decreases, the crystallization of organic materials due to Joule heating generated during operation decreases, which tends to result in a longer lifespan. However, efficiency cannot be maximized simply by improving the organic layer. This is because long lifespan and high efficiency can be achieved simultaneously when the energy level and T1 value between each organic layer, and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined.

[0005] Therefore, in order to fully utilize the excellent characteristics of organic electronic devices, it is necessary to develop materials that form the organic layer within the device, especially hole transport layer materials.

[0006] The purpose of the present invention is to provide a compound for an organic electric device that can lower the driving voltage of the device and improve the luminous efficiency and lifespan of the device, an organic electric device using the same, and an electronic device thereof.

[0007] In one aspect, the present invention provides a compound represented by the following chemical formula:

[0008]

[0009] In another aspect, the present invention provides an organic electric element and an electronic device thereof comprising a compound represented by the above chemical formula.

[0010] By using a compound according to an embodiment of the present invention, the driving voltage of the device can be lowered, and the luminous efficiency and lifespan can be improved.

[0011] Figures 1 to 3 are exemplary diagrams of organic light-emitting devices according to embodiments of the present invention.

[0012] [Explanation of symbols]

[0013] 100, 200, 300: Organic electroluminescent element 110: First electrode

[0014] 120: Hole injection layer 130: Hole transport layer

[0015] 140: Emitting layer 150: Electron transport layer

[0016] 160: Electron injection layer 170: Second electrode

[0017] 180: Light efficiency improvement layer 210: Buffer layer

[0018] 220: Light-emitting auxiliary layer 320: First hole injection layer

[0019] 330: First hole transport layer 340: First light-emitting layer

[0020] 350: First electron transport layer 360: First charge generation layer

[0021] 361: Second charge generation layer 420: Second hole injection layer

[0022] 430: Second hole transport layer 440: Second light-emitting layer

[0023] 450: Second electron transport layer CGL: Charge generation layer

[0024] ST1: First stack ST2: Second stack

[0025] The terms "aryl group," "arylene group," and "aromatic ring" used herein mean a hydrocarbon aromatic ring group, each having 6 to 60 carbon atoms unless otherwise specified, but is not limited thereto. In the present invention, the aryl group or arylene group includes a monocyclic ring, a polycyclic ring, a condensed ring, and the like.

[0026] As used herein, the term "fluorenyl group" means a substituted or unsubstituted fluorenyl group, and "fluorenylene group" means a substituted or unsubstituted fluorenylene group. The fluorenyl group or fluorenylene group used in the present invention includes a spiro compound formed by R and R' bonding to each other in the structure below, and also includes a compound in which adjacent R" bonds to each other to form a ring. The "substituted fluorenyl group" and the "substituted fluorenylene group" mean that at least one of R, R', and R" in the structure below is a substituent other than hydrogen, and the number of R" in the chemical formula below may be 1 to 8. In the present specification, regardless of the valence, a fluorenyl group, a fluorenylene group, etc. may be described as a fluorene group or fluorene.

[0027]

[0028] The term "spiro compound" as used herein has a "spiro linkage," which means a linkage formed by two rings sharing only one atom. The atom shared between the two rings is called a "spiro atom," and depending on the number of spiro atoms contained in a compound, these are called "monospiro-," "dicepiro-," and "trispiro-" compounds, respectively.

[0029] The term "heterocyclic group" used herein includes not only aromatic heterocycles such as "heteroaryl group" or "heteroarylene group" but also non-aromatic heterocycles, and unless otherwise stated means, but is not limited to, a ring having 2 to 60 carbon atoms each containing one or more heteroatoms. The term "heteroatom" used herein, unless otherwise stated, represents an element other than carbon, such as N, O, S, P, or Si, and may include a heteroatom group such as SO2, P=O, etc. instead of carbon forming the ring, as in the following compounds.

[0030]

[0031] In addition, a heterocyclic group includes a monocyclic ring, polycyclic ring, or condensed ring containing a heteroatom, and in the case of a condensed ring, if at least one of the condensed rings is a ring containing a heteroatom, it is defined as a heterocyclic ring. For example, a condensed ring in which a heterocyclic ring such as furan, dihydrofuran, thiophene, pyrrole, pyridine, etc. and an aromatic ring such as benzene, naphthalene, phenanthrene, etc. are condensed, or an aliphatic ring such as cyclopentane, cyclohexane, etc. are condensed is also considered a heterocyclic ring, and a spiro compound in which at least one ring contains a heteroatom is also considered a heterocyclic ring.

[0032] The term "aliphatic ring" used in this specification refers to a cyclic hydrocarbon other than an aromatic hydrocarbon, including a monocyclic ring, a polycyclic ring, a condensed ring, a spiro compound, etc., and unless otherwise stated, refers to a ring having 3 to 60 carbon atoms, but is not limited thereto. In particular, an aliphatic ring (group) in this specification is defined as a hydrocarbon ring that does not contain any aromatic rings. Therefore, not only a saturated hydrocarbon ring such as a cycloalkyl group, but also a ring having one or more double bonds in the ring is considered to be an aliphatic ring as long as it is not an aromatic hydrocarbon.

[0033] The term "fused ring(group)" or "condensed ring(group)" used herein, unless otherwise stated, means a ring in which an aliphatic ring and an aromatic hydrocarbon (aromatic ring group or aryl ring) are condensed with each other, and unless otherwise stated, means a ring in which an aliphatic ring having 3 to 60 carbon atoms and an aromatic hydrocarbon having 6 to 60 carbon atoms are condensed with each other.

[0034] The term “silane group” as used herein means a substituted or unsubstituted silane group unless otherwise stated.

[0035] In this specification, the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc., which are exemplified as examples of each symbol and its substituent, may be described as the 'group name reflecting the valence', or may be described as the 'parent compound name'. For example, in the case of 'phenanthrene', which is a type of aryl group, the name of the group may be described by distinguishing the valence, such as 'phenanthryl' for the monovalent 'group' and 'phenantrylene' for the divalent group, or it may be described as the parent compound name 'phenanthrene' regardless of the valence. Similarly, in the case of pyrimidine, it may be described as 'pyrimidine' regardless of the valence, or it may be described as the 'group name' of the corresponding valence, such as pyrimidinyl group for monovalent and pyrimidinylene for divalent.

[0036] In addition, in this specification, numbers or alphabets indicating positions may be omitted when describing compound names or substituent names. For example, pyrido[4,3-d]pyrimidine may be described as pyridopyrimidine, benzofuro[2,3-d]pyrimidine as benzofuropyrimidine, 9,9-dimethyl-9H-fluorene as dimethylfluorene, etc. Accordingly, both benzo[g]quinoxaline and benzo[f]quinoxaline may be described as benzoquinoxaline.

[0037] Additionally, unless explicitly stated otherwise, the chemical formulas used in the present invention are applied in the same manner as the substituent definitions by the index definitions of the chemical formulas below.

[0038]

[0039] Here, if a is an integer of 0, the substituent R 1 means that it is absent, that is, when a is 0, it means that all the carbons forming the benzene ring are bonded with hydrogen, and in this case, the indication of hydrogen bonded to carbon can be omitted and the chemical formula or compound can be described. In addition, when a is an integer of 1, one substituent R 1 It binds to one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it can bind as follows, for example, and when a is an integer of 4 to 6, it binds to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R 1 may be the same or different.

[0040]

[0041] In addition, unless otherwise stated herein, a ring refers to an aryl ring, a heteroaryl ring, a fluorene ring, an aliphatic ring, a fused ring, etc., and a number-ring refers to a condensed ring, and a number-atom ring refers to a ring shape. For example, naphthalene corresponds to a two-ring condensed ring, anthracene corresponds to a three-ring condensed ring, thiophene and furan correspond to a five-membered heterocycle, and benzene and pyridine correspond to a six-membered aromatic ring.

[0042] In addition, unless otherwise stated in this specification, the rings formed by bonding adjacent groups to each other are C6~C 60 Aromatic ring group; Fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring group; and C3~C 60 Aliphatic ring and C6~C 60The aromatic ring may be selected from the group consisting of a fused ring group. Here, the aromatic ring group may be an aryl ring, and the heterocyclic group may include a heteroaryl ring.

[0043] Unless otherwise stated herein, 'neighboring groups' includes, for example, R1 and R2, R2 and R3, R3 and R4, R5 and R6, as well as R7 and R8 sharing a carbon, and may also include substituents bonded to non-adjacent ring elements (carbon, nitrogen, etc.), such as R1 and R7, R1 and R8, or R4 and R5. That is, when there is a substituent on a ring element such as a carbon or nitrogen that is immediately adjacent, they can be neighboring groups, but when no substituent is bonded to the ring element at the immediately adjacent position, the substituent bonded to the next ring element can be a neighboring group, and substituents bonded to the same ring carbon can also be neighboring groups. In the following chemical formula, when substituents bonded to the same carbon, such as R7 and R8, bond to each other to form a ring, a compound including a spiro moiety can be formed.

[0044] ,

[0045] Additionally, in this specification, the expression 'adjacent groups can combine with each other to form a ring' is used with the same meaning as 'adjacent groups combine with each other to selectively form a ring', and means a case where at least one pair of adjacent groups combine with each other to form a ring.

[0046] In addition, unless otherwise stated herein, substituents such as aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, alkylthio group, arylthio group, etc., rings formed by bonding adjacent groups to each other, etc., are each deuterium; halogen; cyano group; nitro group; siloxane group; C6-C 30 Aryl group of; Fluorenyl group; C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 30 Heterocyclic group of; C3-C 30 Aliphatic ring group; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C1-C 20 alkyl group of; C2-C 20 alkenyl group of; C2-C 20 Alkynyl group of; C1-C 20 Alkoxy group of; C6-C 20 Aryloxy group of; C1-C 20 Alkylthio group of; C6-C 20 Arylthio group of; C1-C 20 Alkyl group or C6-C 20 A silane group substituted or unsubstituted with an aryl group; and C1-C 20 Alkyl group or C6-C 20 It may be substituted with one or more substituents selected from the group consisting of phosphine oxide groups substituted or unsubstituted with an aryl group.

[0047] Hereinafter, the laminated structure of an organic electric device including the compound of the present invention will be described with reference to FIGS. 1 to 3.

[0048] When assigning reference numerals to components in each drawing, it should be noted that identical components are assigned the same numerals whenever possible, even if they appear on different drawings. Furthermore, when describing the present invention, if a detailed description of a related known configuration or function is deemed likely to obscure the gist of the present invention, such detailed description will be omitted.

[0049] When describing components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are only intended to distinguish the components from other components, and the nature, order, or sequence of the components are not limited by the terms. When it is described that a component is "connected," "coupled," or "connected" to another component, it should be understood that the component may be directly connected or connected to the other component, but another component may also be "connected," "coupled," or "connected" between each component.

[0050] Furthermore, when a component such as a layer, membrane, region, or plate is said to be "on" or "over" another component, it should be understood that this includes not only the case where it is "directly on" the other component, but also the case where there are other components in between. Conversely, when a component is said to be "directly on" another part, it should be understood that there are no other components in between.

[0051] Figures 1 to 3 are exemplary diagrams of organic electric devices according to embodiments of the present invention.

[0052] Referring to FIG. 1, an organic electric element (100) according to one embodiment of the present invention includes a first electrode (110), a second electrode (170), and an organic layer formed between the first electrode (110) and the second electrode (170) formed on a substrate (not shown), and an inorganic layer may be included between the first electrode (110) and the second electrode (120).

[0053] For example, the first electrode (110) may be an anode, the second electrode (170) may be a cathode, and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

[0054] The above organic layer refers to a layer containing at least one organic material. For example, the organic layer may include a hole injection layer (120), a hole transport layer (130), a light-emitting layer (140), an electron transport layer (150), and an electron injection layer (160). However, the electron injection layer (160) may be an inorganic layer that does not contain an organic material.

[0055] Specifically, a hole injection layer (120), a hole transport layer (130), a light-emitting layer (140), an electron transport layer (150), and an electron injection layer (160) can be sequentially formed on a first electrode (110).

[0056] Preferably, a light efficiency improvement layer (180) may be formed on one side of the first electrode (110) or the second electrode (170) that is not in contact with the organic layer or the inorganic layer, and when the light efficiency improvement layer (180) is formed, the light efficiency of the organic electric element may be improved.

[0057] For example, a light efficiency improvement layer (180) can be formed on the second electrode (170). In the case of a top emission organic light emitting device, the formation of the light efficiency improvement layer (180) can reduce optical energy loss due to SPPs (surface plasmon polaritons) in the second electrode (170), and in the case of a bottom emission organic light emitting device, the light efficiency improvement layer (180) can serve as a buffer for the second electrode (170).

[0058] 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), which will be described with reference to FIG. 2.

[0059] Referring to FIG. 2, an organic electric element (200) according to another embodiment of the present invention may include a hole injection layer (120), a hole transport layer (130), a buffer layer (210), a light-emitting auxiliary layer (220), a light-emitting layer (140), an electron transport layer (150), an electron injection layer (160), and a second electrode (170) sequentially formed on a first electrode (110), and a light efficiency improvement layer (180) may be formed on the second electrode.

[0060] Although not shown in FIG. 2, an electron transport auxiliary layer may be further formed between the light-emitting layer (140) and the electron transport layer (150).

[0061] Additionally, according to another embodiment of the present invention, the organic layer may be formed in a form in which a plurality of stacks including a hole transport layer, a light-emitting layer, and an electron transport layer are formed. This will be described with reference to FIG. 3.

[0062] Referring to FIG. 3, an organic electric element (300) according to another embodiment of the present invention may have two or more sets of stacks (ST1, ST2) of organic layers formed of multiple layers formed between a first electrode (110) and a second electrode (170), and a charge generation layer (CGL) may be formed between the stacks of organic layers.

[0063] Specifically, an organic electric device according to one embodiment of the present invention may include a first electrode (110), a first stack (ST1), a charge generation layer (CGL: Charge Generation Layer), a second stack (ST2), a second electrode (170), and a light efficiency improvement layer (180).

[0064] The first stack (ST1) is an organic layer formed on the first electrode (110), which may include a first hole injection layer (320), a first hole transport layer (330), a first light-emitting layer (340), and a first electron transport layer (350), and the second stack (ST2) may include a second hole injection layer (420), a second hole transport layer (430), a second light-emitting layer (440), and a second electron transport layer (450). In this way, the first stack and the second stack may be organic layers having the same stacked structure, but may also be organic layers having different stacked structures.

[0065] A charge generation layer (CGL) may be formed between the first stack (ST1) and the second stack (ST2). The charge generation layer (CGL) may include a first charge generation layer (360) and a second charge generation layer (361). This charge generation layer (CGL) is formed between the first light-emitting layer (340) and the second light-emitting layer (440) to increase the current efficiency generated in each light-emitting layer and to smoothly distribute charges.

[0066] The first light-emitting layer (340) may include a light-emitting material including a blue fluorescent dopant in a blue host, and the second light-emitting layer (440) may include a material doped with a greenish yellow dopant and a red dopant in a green host, but the materials of the first light-emitting layer (340) and the second light-emitting layer (440) according to the embodiment of the present invention are not limited thereto.

[0067] In FIG. 3, n can be an integer from 1 to 5, and when n is 2, a charge generation layer (CGL) and a third stack can be additionally stacked on the second stack (ST2).

[0068] When a plurality of light-emitting layers are formed by a multi-layer stack structure as shown in Fig. 3, not only can an organic light-emitting device that emits white light be manufactured by the mixing effect of the light emitted from each light-emitting layer, but an organic light-emitting device that emits light of various colors can also be manufactured.

[0069] The compound represented by the chemical formula 1 of the present invention may be included in an organic layer. For example, the compound represented by the chemical formula 1 of the present invention may be used as a material for a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer (210), a light-emitting auxiliary layer (220), an electron transport layer (150, 350, 450), a light-emitting layer (140, 340, 440), or a light efficiency improvement layer (180), but may preferably be used as a material for a hole transport layer (130, 330, 430).

[0070] Even if the core is identical or similar, the band gap, electrical properties, and interface properties can vary depending on which substituent is bonded at which position. Therefore, research on the selection of the core and the combination of sub-substituents bonded to it is necessary. In particular, when the energy level and T1 value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined, long life and high efficiency can be achieved simultaneously.

[0071] Therefore, in the present invention, by using the compound represented by chemical formula 1 as a material of the hole transport layer (130, 330, 430), the energy level and T1 value between each organic layer, and the inherent properties of the material (mobility, interface properties, etc.) can be optimized, thereby simultaneously improving the lifespan and efficiency of the organic electric device.

[0072] An organic light emitting diode according to an embodiment of the present invention may be manufactured using various deposition methods. It may be manufactured using a deposition method such as PVD or CVD. For example, it may be manufactured by forming an anode (110) by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, forming an organic layer including a hole injection layer (120), a hole transport layer (130), a light emitting layer (140), an electron transport layer (150), and an electron injection layer (160) thereon, and then depositing a material that can be used as a cathode (170) thereon. In addition, an emission auxiliary layer (220) may be further formed between the hole transport layer (130) and the light emitting layer (140), and an electron transport auxiliary layer (not shown) may be further formed between the emission layer (140) and the electron transport layer (150), or may be formed in a stack structure as described above.

[0073] In addition, the organic layer can be manufactured with a smaller number of layers by using various polymer materials and a solution process or solvent process other than a deposition method, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, a doctor blading process, a screen printing process, or a thermal transfer method. Since the organic layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the formation method.

[0074] An organic electric device according to one embodiment of the present invention may be a front-emitting, back-emitting, or double-sided emitting type depending on the material used.

[0075] In addition, the organic electric device according to one embodiment of the present invention may be selected from the group consisting of an organic light-emitting device, an organic solar cell, an organic photoconductor, an organic transistor, a device for monochrome lighting, and a device for quantum dot display.

[0076] Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including 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 cell phones, navigation systems, game consoles, various TVs, and various computers.

[0077] Hereinafter, a compound according to one aspect of the present invention will be described.

[0078] A compound according to one aspect of the present invention is represented by the following chemical formula 1.

[0079] <Chemical Formula 1>

[0080]

[0081] In the above chemical formula 1, each symbol is defined as follows.

[0082] Ar 1 Silver C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring group; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C1~C 30 An alkyl group; and a silane group are selected from the group consisting of:

[0083] R 1 and R 2 are independently C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring group; C3~C 60 Aliphatic ring and C6~C 60 A fused ring group of an aromatic ring; and C1~C 30 is selected from the group consisting of alkyl groups, and R1 and R 2 can combine with each other to form rings.

[0084] R 3 Inland R 8 are independently hydrogen; deuterium; halogen; cyano group; nitro group; C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring group; C6~C 60 Aromatic ring and C3~C 60 Fused ring group of aliphatic ring; C1~C 20 alkyl group of; and silane group, and is selected from the group consisting of adjacent R 3 Kiri, neighboring R 4 Kiri, neighboring R 6 Kiri, neighboring R 7 They can combine with each other to form rings, and neighboring R 5 R in pairs or neighboring pairs 8 Compounds that are bonded to each other to form a ring are excluded from the compounds of the present invention.

[0085] a and c are each an integer from 0 to 4, b is each an integer from 0 to 3, d is each an integer from 0 to 5, e is each an integer from 0 to 3, f is each an integer from 0 to 7, and if these are integers greater than or equal to 2, a plurality of R 1 Each or multiple R 8 Each is either the same or different from the other.

[0086] Even if c or f is an integer greater than or equal to 2, the neighboring R 5 R in pairs or neighboring pairs 8 They do not form rings.

[0087] Neighboring units, for example, neighboring R 1 and R 2 Kiri, neighboring R 3 Kiri, neighboring R 4 Kiri, neighboring R 6Kiri, neighboring R 7 When they combine with each other to form a ring, the ring is C6~C 60 Aromatic ring group; Fluorenyl group; C3~C 60 Aliphatic ring group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; and C3~C 60 Aliphatic ring and C6~C 60 It can be selected from the group consisting of fused ring groups of aromatic rings.

[0088] R 1 and R 2 When they combine with each other to form a ring, a spiro compound can be formed. For example, R 1 and R 2 When they are bonded to each other to form a fluorene ring, a structure containing a spirobenzofluorenefluorene moiety can be formed, and R 1 and R 2 They can also combine with each other to form aliphatic rings such as cyclohexane, bicycloheptane, and adamantyl.

[0089] Neighboring neighboring R 1 and R 2 Kiri, neighboring R 3 Kiri, neighboring R 4 Kiri, neighboring R 6 Kiri, neighboring R 7 When at least one pair of them combines with each other to form an aromatic ring, the aromatic ring is, for example, C6~C 20 , C6~C 18 , C6~C 16 , C6~C 14 , C6~C 13 , C6~C 12 , C6~C 10 , C6, C 10 , C 12 , C 14 , C 15 , C 16 , C 18It may be an aromatic ring, such as benzene, naphthalene, anthracene, phenanthrene, pyrene, etc.

[0090] Neighboring neighboring R 1 and R 2 Kiri, neighboring R 3 Kiri, neighboring R 4 Kiri, neighboring R 6 Kiri, neighboring R 7 When at least one pair of them combines with each other to form an aliphatic ring, the aliphatic ring is, for example, C3~C 20 , C3~C 19 , C3~C 18 , C3~C 17 , C3~C 16 , C3~C 15 , C3~C 14 , C3~C 13 , C3~C 12 , C3~C 11 , C3~C 10 , C3~C8, C3~C6, C6, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 It may be an aliphatic ring, such as cyclobutane, cyclopentane, cyclohexane, bicycloheptane, adamantyl, etc.

[0091] Neighboring neighboring R 1 and R 2 Kiri, neighboring R 3 Kiri, neighboring R 4 Kiri, neighboring R 6 Kiri, neighboring R 7 When at least one pair of them combines with each other to form a fused ring, the fused ring is, for example, C6~C 20 , C6~C 18 , C6~C 16 , C6~C 14 , C6~C 13 , C6~C12 , C6~C 10 , C6, C 10 , C 12 , C 14 , C 15 , C 16 , C 18 Aromatic rings such as C3~C 20 , C3~C 19 , C3~C 18 , C3~C 17 , C3~C 16 , C3~C 15 , C3~C 14 , C3~C 13 , C3~C 12 , C3~C 11 , C3~C 10 , C3~C8, C3~C6, C6, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 It may be a fused ring of an aliphatic ring, and specifically, it may be 1,2,3,4-tetrahydronaphthalene, which is a fused ring of benzene and cyclohexane, or a fused ring of benzene and cyclopentane.

[0092] The above Ar 1 , R 1 Inland R 8 If at least one of them is an aryl group, the aryl group is, for example, C6~C 30 , C6~C 29 , C6~C 28 , C6~C 27 , C6~C 26 , C6~C 25 , C6~C 24 , C6~C 23 , C6~C 22 , C6~C 21 , C6~C 20 , C6~C 19 , C6~C 18 , C6~C 17 , C6~C 16, C6~C 15 , C6~C 14 , C6~C 13 , C6~C 12 , C6~C 11 , C6~C 10 , C6, C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 It may be an aryl group such as, for example, phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, triphenylene, etc.

[0093] The above Ar 1 , R 1 Inland R 8 If at least one of them is a heterocyclic group, the heterocyclic group is, for example, C2~C 30 , C2~C 29 , C2~C 28 , C2~C 27 , C2~C 26 , C2~C 25 , C2~C 24 , C2~C 23 , C2~C 22 , C2~C 21 , C2~C 20 , C2~C 19 , C2~C 18 , C2~C 17 , C2~C 16 , C2~C 15 , C2~C 14 , C2~C 13 , C2~C 12 , C2~C 11 , C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C16 , 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 It may be a heterocyclic group such as, and specifically, pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, indene, indole, phenyl-indole, benzoindole, phenyl-benzoindole, pyrazinoindole, quinoline, isoquinoline, benzoquinoline, pyridoquinoline, quinazoline, benzoquinazoline, dibenzoquinazoline, phenanthroquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, benzofuran, naphthobenzofuran, dibenzofuran, dinaphthofuran, phenanthrobenzofuran, thiophene, benzothiophene, dibenzothiophene, naphthobenzothiophene, dinaphthothiophene, phenantrobenzothiophene, carbazole, phenyl-carbazole, Benzocarbazole, phenyl-benzocarbazole, naphthyl-benzocarbazole, dibenzocarbazole, indolocarbazole, benzofuropyridine, benzothiopyridine, benzofuropyridine, benzothiopyrimidine, benzofuropyrimidine, benzothiopyrazine, benzofuropyrazine, benzimidazole, benzothiazole, benzosilole, phenanthroline, dihydro-phenylphenazine, 10-phenyl-10H-phenoxazine, phenoxazine, phenothiazine, dibenzodioxin, benzodibenzodioxin, thianthrene, oxazole, benzoxazole, naphthooxazole, phenanthrooxazole, dibenzothiobenzoxazole, dibenzofurobenzoxazole, It may be 9,9-dimethyl-9H-xanthrene, 9,9-dimethyl-9H-thioxanthrene, dihydrodimethylphenylacridine, spiro[fluorene-9,9'-xanthene], etc.

[0094] The above Ar 1 , R 1 Inland R 8 If one of them is an aliphatic ring group, the aliphatic ring group is, for example, C3~C 30, C3~C 29 , C3~C 28 , C3~C 27 , C3~C 26 , C3~C 25 , C3~C 24 , C3~C 23 , C3~C 22 , C3~C 21 , C3~C 20 , C3~C 19 , C3~C 18 , C3~C 17 , C3~C 16 , C3~C 15 , C3~C 14 , C3~C 13 , C3~C 12 , C3~C 11 , C3~C 10 , C3~C8, C3~C6, C6, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 It may be an aliphatic ring group such as cyclobutane, cyclopentane, cyclohexane, bicycloheptane, adamantyl, etc.

[0095] The above Ar 1 , R 1 Inland R 8 When at least one of them is a fluorenyl group, the fluorenyl group may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[b]fluorene-11,9'-fluorene], benzo[b]fluorene, 11,11-diphenyl-11H-benzo[b]fluorene, 9-(naphthalen-2-yl)9-phenyl-9H-fluorene, etc.

[0096] The above Ar 1 , R 1 Inland R 8 If at least one of them is an alkyl group, the alkyl group is, for example, C1~C 20, C1~C 10 , C1~C4, C1, C2, C3, C4, etc., and may be, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, etc.

[0097] The above aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, silane group, and ring formed by bonding adjacent groups each contain deuterium; halogen; C1-C 20 Alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 Alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; nitro group; C1-C 20 Alkylthio group of; C1-C 20 Alkoxy group of; C6-C 30 Arylthio group of; C6-C 30 Aryloxy group of; C1-C 20 alkyl group of; C2-C 20 alkenyl group of; C2-C 20 Alkynyl group of; C6-C 30 Aryl group of; fluorenyl group; C2-C containing at least one heteroatom among O, N, S, Si and P 30 Heterocyclic group of; C3-C 30 Aliphatic ring group; and C6-C 30 Aromatic ring and C3-C 30 It can be substituted with one or more substituents selected from the group consisting of fused ring groups of an aliphatic ring, and adjacent substituents can be combined with each other to form a ring, and hydrogen of the substituents can be replaced with deuterium.

[0098] When at least one of the above aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, silane group, or ring formed by bonding adjacent groups is substituted with an aryl group, the aryl group is, for example, C6~C 30 , C6~C 29 , C6~C28 , C6~C 27 , C6~C 26 , C6~C 25 , C6~C 24 , C6~C 23 , C6~C 22 , C6~C 21 , C6~C 20 , C6~C 19 , C6~C 18 , C6~C 17 , C6~C 16 , C6~C 15 , C6~C 14 , C6~C 13 , C6~C 12 , C6~C 11 , C6~C 10 , C6, C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 It can be an aryl group such as .

[0099] When at least one of the above aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, silane group, or ring formed by bonding adjacent groups is substituted with an aliphatic ring group, the aliphatic ring group is, for example, C3~C 30 , C3~C 29 , C3~C 28 , C3~C 27 , C3~C 26 , C3~C 25 , C3~C 24 , C3~C 23 , C3~C 22 , C3~C 21 , C3~C 20 , C3~C 19 , C3~C 18 , C3~C 17 , C3~C 16 , C3~C 15 , C3~C 14 , C3~C 13 , C3~C 12, C3~C 11 , C3~C 10 , C3~C8, C3~C6, C6, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 It may be an aliphatic ring such as the back.

[0100] When at least one of the above aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, silane group, or ring formed by bonding adjacent groups to each other is substituted with an alkyl group, the alkyl group is, for example, C1~C 20 , C1~C 10 , C1~C4, C1, C2, C3, C4, etc., and may be, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, etc.

[0101] The above chemical formula 1 may be represented by one of the following chemical formulas 1-1 to 1-4, but is not limited thereto.

[0102] <Chemical Formula 1-1> <Chemical Formula 1-2>

[0103]

[0104] <Chemical Formula 1-3> <Chemical Formula 1-4>

[0105]

[0106] In the above chemical formulas 1-1 to 1-4, Ar 1 , R 3 Inland R 8 , a to f are as defined in chemical formula 1, and R 3' is R of chemical formula 1 3 is defined identically to R 4' is R of chemical formula 1 4 is defined identically to , except that R 3' Wow R 4'Except when it is hydrogen. In the above chemical formulas 1-1 to 1-4, the hydrogen of the methyl group of the 9,9-dimethyl-9H-fluorenyl group can be replaced with deuterium.

[0107] The above Ar 1 may be selected from the group consisting of the following chemical formulas Ar-1 to Ar-5, but is not limited thereto.

[0108] <Chemical formula Ar-1> <Chemical formula Ar-2> <Chemical formula Ar-3>

[0109]

[0110] <Chemical formula Ar-4> <Chemical formula Ar-5>

[0111]

[0112] In the above chemical formulas Ar-1 to Ar-5, represents a binding site, and each symbol can be defined as follows.

[0113] L 1 is a single bond; C6~C 60 Arylene group; Fluorenylene group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring group; C3~C 60 Aliphatic ring and C6~C 60 A fused ring group of an aromatic ring; and C1~C 30 is selected from the group consisting of alkylene groups.

[0114] X is O, S, N(R), C(R')(R") or Si(R')(R").

[0115] R 11 Inland R 13 , R' and R" are independently hydrogen; deuterium; halogen; C1-C 20 Alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20Alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; nitro group; C1-C 20 Alkylthio group of; C1-C 20 Alkoxy group of; C6-C 30 Arylthio group of; C6-C 30 Aryloxy group of; C1-C 20 alkyl group of; C2-C 20 alkenyl group of; C2-C 20 Alkynyl group of; C6-C 30 Aryl group of; fluorenyl group; C2-C containing at least one heteroatom among O, N, S, Si and P 30 Heterocyclic group of; C3-C 30 Aliphatic ring group; and C6-C 30 Aromatic ring and C3-C 30 It is selected from the group consisting of fused ring groups of aliphatic rings, and adjacent groups can combine with each other to form a ring.

[0116] The above R is C1-C 20 alkyl group of; C6-C 30 Aryl group of; fluorenyl group; C2-C containing at least one heteroatom among O, N, S, Si and P 30 Heterocyclic group of; C3-C 30 Aliphatic ring group; and C6-C 30 Aromatic ring and C3-C 30 It is selected from the group consisting of fused ring groups of aliphatic rings.

[0117] m is an integer from 0 to 5, n is an integer from 0 to 3, o is an integer from 0 to 4, and if these are integers greater than or equal to 2, then multiple R 11 Each, multiple R 12 Each, multiple R 13 Each is either the same or different from the other.

[0118] Specifically, the compound represented by the above chemical formula 1 may be one of the following compounds, but is not limited thereto.

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146] .

[0147] In another aspect, the present invention provides an organic electric device comprising a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, wherein the organic layer comprises a compound represented by Chemical Formula 1. Preferably, the compound of Chemical Formula 1 is contained in a hole transport region of the organic layer, more preferably, in the hole transport layer.

[0148] In another aspect, the present invention provides an electronic device including a display device including an organic electric element and a control unit for driving the display device, wherein the organic electric element includes a compound represented by the chemical formula 1.

[0149] In another aspect, the present invention provides a compound represented by the chemical formula 1 obtained by recovering and purifying the material of an organic layer from a deposition device after depositing the organic layer in a manufacturing process of an organic electric device. The purity of the compound obtained by recovery and purification is 99.9% or higher.

[0150] In another aspect, the present invention provides a method for recovering a compound, comprising the steps of depositing an organic layer material including a compound represented by Chemical Formula 1, recovering the organic layer material attached to a deposition device, and purifying the recovered organic layer material to obtain a compound represented by Chemical Formula 1 having a purity of 99.9% or higher.

[0151] The above purification step may include a step of recrystallizing the recovered organic layer material using a recrystallization solvent, a step of adsorption separation using an adsorbent, and a step of sublimation purification.

[0152] The above recrystallization step may include a preliminary purification process for obtaining a compound represented by the above chemical formula 1 with a purity of 98% using a recrystallization solvent.

[0153] A polar solvent having a polarity index (PI) of 5.5 to 7.2 is preferably used as the recrystallization solvent, or a mixture of a polar solvent having a polarity index of 5.5 to 7.2 and a non-polar solvent having a polarity index of 2.0 to 4.7 may be used.

[0154] When using a mixture of a polar solvent and a non-polar solvent as a recrystallization solvent, the non-polar solvent may be used in a ratio of 15% (v / v) or less compared to the polar solvent.

[0155] In addition, as a recrystallization solvent, a single solvent of methylpyrrolidone (N-methylpyrrolidone: NMP) is preferably used; or a mixed polar solvent in which any one selected from the group consisting of methylpyrrolidone, dimethyl imidazolidinone (1,3-dimethyl-2-imidazolidinone), 2-pyrrolidone, dimethylformamide (N,N-dimethyl formamide), dimethyl acetamide, and dimethyl sulfoxide is mixed; or a single or mixed nonpolar solvent selected from the group consisting of toluene, dichloromethane (DCM), dichloroethane (DCE), tetrahydrofuran (THF), chloroform, ethyl acetate, and butanone, or a mixture of polar solvents and nonpolar solvents can be used.

[0156] The above preliminary purification process may include a step of dissolving the unrefined organic light-emitting material recovered from the deposition equipment in a polar solvent at 90°C to 120°C and then cooling it to 0°C to 5°C to precipitate crystals.

[0157] The above preliminary purification process may include a step of dissolving an unrefined organic light-emitting material recovered from a deposition device in a polar solvent at 90°C to 120°C, cooling to 35°C to 40°C, adding a non-polar solvent, and then cooling to 0°C to 5°C to precipitate a crystal.

[0158] The above preliminary purification process may include a step of dissolving the crude organic light-emitting material recovered from the deposition equipment in a non-polar solvent, concentrating the solvent, and precipitating crystals while removing the non-polar solvent.

[0159] The above preliminary purification process may include a step of first recrystallizing with a polar solvent and then recrystallizing again with a non-polar solvent.

[0160] In the adsorption separation step using the above adsorbent, activated carbon, silica gel, alumina or a known material for adsorption purposes can be used as the adsorbent.

[0161] Hereinafter, examples of synthesis of a compound represented by Chemical Formula 1 according to the present invention and examples of manufacturing an organic electric device will be described in detail by way of examples, but the present invention is not limited thereto.

[0162] [Synthesis example]

[0163] The compound represented by chemical formula 1 according to the present invention (final product) can be manufactured as in the following reaction scheme 1, but is not limited thereto.

[0164] <Reaction Scheme 1> (Hal 1 is Br, I or Cl)

[0165]

[0166] Synthesis example of Sub 1

[0167] Sub 1 of the above reaction scheme 1 can be manufactured according to the following reaction scheme 2, but is not limited thereto.

[0168] <Reaction Scheme 2> (Hal 2 is Br, I or Cl)

[0169]

[0170] 1. Synthesis example of Sub1-1

[0171]

[0172] Sub 1a-1 (11.0 g, 40.3 mmol) was dissolved in toluene (134 mL), and then Sub 1b-1 (14.2 g, 48.3 mmol), Pd2(dba)3 (1.11 g, 1.2 mmol), Xphos (9.6 g, 20.1 mmol), and NaOt-Bu (7.7 g, 80.5 mmol) were added and stirred at 80 °C. Upon completion of the reaction, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The concentrate was then separated using a silica gel column and recrystallized to obtain 15.9 g of the product (yield: 81%).

[0173] 2. Synthesis example of Sub1-15

[0174]

[0175] After dissolving Sub 1a-2 (10.0 g, 34.8 mmol) in toluene (116 mL), Sub 1b-2 (12.3 g, 41.7 mmol), Pd2(dba)3 (0.96 g, 1.0 mmol), Xphos (8.30 g, 17.4 mmol), and NaOt-Bu (6.69 g, 69.6 mmol) were added, and the same method as the synthesis example of Sub1-1 was followed to obtain 13.1 g of the product (yield: 75%).

[0176] 3. Synthesis example of Sub1-23

[0177]

[0178] After dissolving Sub 1a-3 (12.1 g, 34.3 mmol) in toluene (130 mL), Sub 1b-1 (12.2 g, 41.1 mmol), Pd2(dba)3 (0.94 g, 1.0 mmol), Xphos (8.17 g, 17.1 mmol), and NaOt-Bu (6.6 g, 68.5 mmol) were added, and the same method as the synthesis example of Sub1-1 was followed to obtain 15.0 g of the product (yield: 77%).

[0179] 4. Synthesis example of Sub1-57

[0180]

[0181] After dissolving Sub 1a-4 (10.0 g, 24.3 mmol) in toluene (115 mL), Sub 1b-2 (8.6 g, 29.2 mmol), Pd2(dba)3 (0.67 g, 0.7 mmol), Xphos (5.8 g, 12.2 mmol), and NaOt-Bu (4.67 g, 48.6 mmol) were added, and the same method as the synthesis example of Sub1-1 was followed to obtain 11.8 g of the product (yield: 78%).

[0182] Compounds belonging to Sub 1 may be, but are not limited to, the compounds below, and the FD-MS (Field Desorption-Mass Spectrometry) values ​​of the compounds below are as shown in Table 1 below.

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198] Compound FD-MS Compound FD-MS Sub1-1 m / z = 487.23 (C 37 H 29 N = 487.65) Sub1-2 m / z = 577.28 (C 44 H 35 N = 577.77) Sub1-3 m / z = 563.26 (C 43 H 33 N = 563.74) Sub1-4 m / z = 557.31 (C 42 H 39 N = 557.78) Sub1-5 m / z = 569.31 (C 43 H 39 N = 569.79) Sub1-6 m / z = 507.31 (C 43 H 26 D7 N = 570.79) Sub1-7 m / z = 557.31 (C 42 H 39 N = 557.78) Sub1-8 m / z = 501.25 (C 38 H 31 N = 501.67) Sub1-9 m / z = 501.25 (C 38 H 31 N = 501.67) Sub1-10 m / z = 611.26 (C 47 H 33 N = 611.79) Sub1-11 m / z = 609.25 (C 47 H 31 N = 609.77) Sub1-12 m / z = 543.29 (C 41 H37 N=543.75)Sub1-13m / z=491.26(C 37 H 25 D4N=491.67)Sub1-14m / z=577.28 (C 44 H 35 N=577.77)Sub1-15m / z=501.25 (C 38 H 31 N=501.67)Sub1-16m / z=639.29 (C 49 H 37 N=639.84)Sub1-17m / z=501.25 (C 38 H 31 N=501.67)Sub1-18m / z=515.26 (C 39 H 33 N=515.70)Sub1-19m / z=501.25 (C 38 H 31 N=501.67)Sub1-20m / z=563.26 (C 43 H 33 N=563.74)Sub1-21m / z=543.29 (C 41 H 37 N=543.75)Sub1-22m / z=581.31 (C 44 H 39 N=581.80)Sub1-23m / z=568.29(C 43 H 28 D5N=568.77)Sub1-24m / z=569.31 (C 43 H 39 N=569.79)Sub1-25m / z=563.26 (C 43 H 33 N=563.74)Sub1-26m / z=563.26 (C 43 H 33 N=563.74)Sub1-27m / z=593.27(C 44 H 35 NO=593.77)Sub1-28m / z=623.26 (C 48 H 33 N=623.80)Sub1-29m / z=515.26 (C 39 H 33 N=515.70)Sub1-30m / z=687.29 (C53 H 37 N=687.89)Sub1-31m / z=623.26 (C 48 H 33 N=623.80)Sub1-32m / z=563.26 (C 43 H 33 N=563.74)Sub1-33m / z=490.25(C 37 H 26 D3N=490.66)Sub1-34m / z=625.28 (C 48 H 35 N=625.81)Sub1-35m / z=639.29 (C 49 H 37 N=639.84)Sub1-36m / z=623.26 (C 48 H 33 N=623.80)Sub1-37m / z=568.29(C 43 H 28 D5N=568.77)Sub1-38m / z=625.28 (C 48 H 35 N=625.81)Sub1-39m / z=501.25 (C 38 H 31 N=501.67)Sub1-40m / z=501.25 (C 38 H 31 N=501.67)Sub1-41m / z=491.26(C 37 H 25 D4N=491.67)Sub1-42m / z=563.26 (C 43 H 33 N=563.74)Sub1-43m / z=568.29(C 43 H 28 D5N=568.77)Sub1-44m / z=515.26 (C 39 H 33 N=515.70)Sub1-45m / z=691.32(C 53 H 41 N=5691.92)Sub1-46m / z=487.23 (C 37 H 29 N=487.65)Sub1-47m / z=577.28 (C 44 H 35N=577.77)Sub1-48m / z=685.28 (C 53 H 35 N=685.87)Sub1-49m / z=563.26 (C 43 H 33 N=563.74)Sub1-50m / z=515.26 (C 39 H 33 N=515.70)Sub1-51m / z=537.25 (C 41 H 31 N=537.71)Sub1-52m / z=501.25 (C 38 H 31 N=501.67)Sub1-53m / z=613.28 (C 47 H 35 N=613.80)Sub1-54m / z=563.26 (C 43 H 33 N=563.74)Sub1-55m / z=543.29 (C 41 H 37 N=543.75)Sub1-56m / z=537.25 (C 41 H 31 N=537.71)Sub1-57m / z=625.28 (C 48 H 35 N=625.81)Sub1-58m / z=685.28 (C 53 H 35 N=685.87)Sub1-59m / z=501.25 (C 38 H 31 N=501.67)Sub1-60m / z=501.25 (C 38 H 31 N=501.67)Sub1-61m / z=687.29 (C 53 H 37 N=687.89)Sub1-62m / z=639.29 (C 49 H 37 N=639.84)Sub1-63m / z=537.25 (C 41 H 31 N=537.71)Sub1-64m / z=611.26 (C 47 H 33 N=611.79)Sub1-65m / z=569.31 (C 43 H39 N=569.79)Sub1-66m / z=621.34 (C 47 H 43 N=621.87)Sub1-67m / z=692.32(C 53 H 32 D5N=692.92)Sub1-68m / z=723.39 (C 55 H 49 N=724.00)Sub1-69m / z=603.29 (C 46 H 37 N=603.81)Sub1-70m / z=568.29(C 43 H 28 D5N=568.77)Sub1-71m / z=619.32 (C 47 H 41 N=619.85)Sub1-72m / z=595.32 (C 45 H 41 N=595.83)Sub1-73m / z=543.29 (C 41 H 37 N=543.75)Sub1-74m / z=564.26 (C 42 H 32 N2=564.73)Sub1-75m / z=593.31 (C 45 H 39 N=593.81)Sub1-76m / z=609.25 (C 47 H 31 N=609.77)Sub1-77m / z=651.39 (C 49 H 49 N=651.94)Sub1-78m / z=502.32(C 37 H 14 D 15 N=502.74)Sub1-79m / z=557.31 (C 42 H 39 N=557.78)Sub1-80m / z=515.26 (C 39 H 33 N=515.70)

[0199] Synthesis example of Sub 2

[0200] Sub 2 of the above reaction scheme 1 can be synthesized by the following reaction scheme 3, but is not limited thereto.

[0201] <Reaction Scheme 3> ((Hal 1 , Hal 3 is Br, I or Cl)

[0202]

[0203] 1. Sub2-1 Synthesis Example

[0204]

[0205] In a round-bottomed flask, add Sub 2c-1 (12.4 g, 79.3 mmol), Sub 2d-1 (20.2 g, 71.3 mmol), Pd(pph3)4 (2.7 g, 2.4 mmol), and NaOH (6.3 g, 158.6 mmol), dissolve in deionized water (100 mL) and toluene (264 mL), and stir at 70 °C. Upon completion of the reaction, extract with CH2Cl2 and water, dry the organic layer over MgSO4, and concentrate. The concentrate was then separated through a silica gel column and recrystallized to obtain 17.2 g of the product (yield: 69%).

[0206] 2. Sub2-8 synthesis example

[0207]

[0208] In a round-bottom flask, (2-bromophenyl)boronic acid (15.8 g, 78.6 mmol), Iodobenzene (14.5 g, 70.8 mmol), Pd(pph3)4 (2.73 g, 2.3 mmol), and NaOH (6.31 g, 60.1 mmol) were added, dissolved in Di Water (80 mL) and Toluene (262 mL), and the mixture was stirred for 18.3 g (yield: 65%) of the product.

[0209] 3. Sub2-13 Synthesis Example

[0210]

[0211] In a round-bottom flask, (4-bromophenyl)boronic acid (16.0 g, 79.6 mmol), 2-iodobicyclo[2.2.1]heptane (15.9 g, 71.7 mmol), Pd(pph3)4 (2.76 g, 2.4 mmol), and Na2CO3 (16.7 g, 159.3 mmol) were added, dissolved in Diwater (100 mL) and Toluene (266 mL), and the mixture was stirred for 100 minutes. The mixture was stirred for 10 minutes in the same manner as in the synthesis example of Sub2-1, to obtain 13.0 g (yield: 65%) of the product.

[0212] 4. Sub2-60 synthesis example

[0213]

[0214] In a round-bottom flask, (4-bromophenyl)boronic acid (18.5 g, 92.1 mmol), (3s,5s,7s)-1-iodoadamantane (21.7 g, 82.9 mmol), Pd(pph3)4 (3.19 g, 2.7 mmol), and Na2CO3 (19.3 g, 184.2 mmol) were added, dissolved in Diwater (120 mL) and Toluene (307 mL), and the same method as the synthesis example of Sub2-1 was used to obtain 14.5 g (yield: 54%) of the product.

[0215] Compounds belonging to Sub 2 may include, but are not limited to, the compounds below, and the FD-MS values ​​of the compounds below are as shown in Table 2 below.

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230] Compound FD-MS Compound FD-MS Sub 2-1 m / z = 314.09 (C 22 H 15 Cl = 314.81) Sub 2-2 m / z = 231.99 (C 12 H9Br = 233.11) Sub 2-3 m / z = 238.04 (C 12 H 15 Br = 239.16) Sub 2-4 m / z = 282.00 (C 16 H 11 Br = 283.17) Sub 2-5 m / z = 314.07 (C 18 H 19 Br = 315.25) Sub 2-6 m / z = 236.01 (C 12 H5D4Br = 237.13) Sub 2-7 m / z = 396.05 (C 25 H 17 Br = 397.31) Sub 2-8 m / z = 231.99 (C 12 H9Br = 233.11) Sub 2-9 m / z = 238.04 (C 12 H 15 Br = 239.16) Sub 2-10 m / z = 308.02 (C 18 H 13 Br = 309.21) Sub 2-11 m / z = 231.99 (C 12 H9Br = 233.11) Sub 2-12 m / z = 260.02 (C 14 H 13 Br = 261.16) Sub 2-13 m / z = 250.04 (C13 H 15 Br=251.17)Sub 2-14m / z=288.05(C 16 H 17 Br=289.22)Sub 2-15m / z=326.07(C 19 H 19 Br=327.26)Sub 2-16m / z=314.09(C 22 H 15 Cl=314.81)Sub 2-17m / z=314.09(C 22 H 15 Cl=314.81)Sub 2-18m / z=238.05(C 16 H 11 Cl=238.71)Sub 2-19m / z=250.04(C 13 H 15 Br=251.17)Sub 2-20m / z=264.07(C 18 H 13 Cl=264.75)Sub 2-21m / z=348.05(C 21 H 17 Br=349.27)Sub 2-22m / z=340.10(C 24 H 17 Cl=340.85)Sub 2-23m / z=414.04(C 24 H 19 BrSi=415.40)Sub 2-24m / z=314.07(C 18 H 19 Br=315.25)Sub 2-25m / z=238.04(C 12 H 15 Br=239.16)Sub 2-26m / z=240.05(C 12 H 17 Br=241.17)Sub 2-27m / z=288.05(C 16 H 17 Br=289.22)Sub 2-28m / z=308.02(C 18 H 13 Br=309.21)Sub 2-29m / z=288.05(C 16 H 17 Br=289.22)Sub 2-30m / z=264.07(C 18 H 13Cl=264.75)Sub 2-31m / z=321.02(C 18 H 12 BrN=322.20)Sub 2-32m / z=246.00(C 13 H 11 Br=247.13)Sub 2-33m / z=323.03(C 18 H 14 BrN=324.22)Sub 2-34m / z=212.02(C 10 H 13 Br=213.12)Sub 2-35m / z=223.94(C7H4BrF3=225.01)Sub 2-36m / z=314.09(C 22 H 15 Cl=314.81)Sub 2-37m / z=240.00(C 13 H 11 Br=247.13)Sub 2-38m / z=180.95(C7H4BrN=182.02)Sub 2-39m / z=256.98(C 13 H8BrN=258.12)Sub 2-40m / z=397.05(C 24 H 16 BrN=398.30)Sub 2-41m / z=320.11(C 18 H 25 Br=321.30)Sub 2-42m / z=260.02(C 14 H 13 Br=261.16)Sub 2-43m / z=322.04(C 19 H 15 Br=323.23)Sub 2-44m / z=264.07(C 18 H 13 Cl=264.75)Sub 2-45m / z=246.00(C 13 H 11 Br=247.13)Sub 2-46m / z=237.02(C 12 H4D5Br=238.14)Sub 2-47m / z=328.06(C 18 H9D5BrN=329.25)Sub 2-48m / z=160.99(C6D5Br=162.04)Sub 2-49m / z=308.02(C 18 H 13Br=309.21)Sub 2-50m / z=337.98(C 18 H 11 BrS=339.25)Sub 2-51m / z=326.07(C 19 H 19 Br=327.26)Sub 2-52m / z=340.10(C 24 H 17 Cl=340.85)Sub 2-53m / z=348.05(C 21 H 17 Br=349.27)Sub 2-54m / z=236.01(C 12 H5D4Br=237.13)Sub 2-55m / z=314.09(C 22 H 15 Cl=314.81)Sub 2-56m / z=288.05(C 16 H 17 Br=289.22)Sub 2-57m / z=340.10(C 24 H 17 Cl=340.85)Sub 2-58m / z=212.02(C 10 H 13 Br=213.12)Sub 2-59m / z=246.00(C 13 H 11 Br=247.13)Sub 2-60m / z=290.07(C 16 H 19 Br=291.23)Sub 2-61m / z=314.09(C 22 H 15 Cl=314.81)Sub 2-62m / z=282.00(C 16 H 11 Br=283.17)Sub 2-63m / z=252.05(C 13 H 17 Br=253.18)Sub 2-64m / z=322.00(C 18 H 11 BrO=323.19)Sub 2-65m / z=352.20(C 24 H 29 Cl=352.95)Sub 2-66m / z=314.09(C 22 H 15 Cl=314.81)Sub 2-67m / z=323.03(C18 H 14 BrN=324.22)Sub 2-68m / z=294.12(C 20 H 19 Cl=294.82)Sub 2-69m / z=246.00(C 13 H 11 Br=247.13)Sub 2-70m / z=308.02(C 18 H 13 Br=309.21)Sub 2-71m / z=314.09(C 22 H 15 Cl=314.81)Sub 2-72m / z=321.02(C 18 H 12 BrN=322.20)Sub 2-73m / z=426.12(C 31 H 19 Cl=426.94)Sub 2-74m / z=364.03(C 20 H 17 BrSi=365.34)Sub 2-75m / z=414.04(C 24 H 19 BrSi=415.40)Sub 2-76m / z=377.08(C 22 H 20 BrN=378.31)Sub 2-77m / z=232.98(C 11 H8BrN=234.10)Sub 2-78m / z=397.05(C 24 H 16 BrN=398.30)Sub 2-79m / z=286.04(C 16 H 15 Br=287.20)Sub 2-80m / z=321.02(C 18 H 12 BrN=322.20)

[0231] 최종화합물의 합성예

[0232] 1. P-15 합성예

[0233]

[0234] Sub 1-15 (11.1 g, 22.1 mmol) was dissolved in toluene (78 mL), and then Sub 2-13 (5.5 g, 22.1 mmol), Pd2(dba)3 (0.6 g, 0.6 mmol), Xphos (5.2 g, 11.1 mmol), and NaOt-Bu (4.2 g, 44.2 mmol) were added and stirred at 85 °C. Upon completion of the reaction, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The concentrate was then separated on a silica gel column and purified by sublimation to obtain 10.4 g of the product (yield: 70%).

[0235] 2. P-20 synthetic example

[0236]

[0237] After dissolving Sub1-14 (10.7 g, 18.5 mmol) in toluene (78 mL), Sub2-18 (4.4 g, 18.5 mmol), Pd2(dba)3 (0.5 g, 0.5 mmol), Xphos (4.4 g, 9.3 mmol), and NaOt-Bu (3.6 g, 37.0 mmol) were added, and the same method as the synthesis example of P-15 was followed to obtain 10.2 g of the product (yield: 71%).

[0238] 3. P-54 synthetic example

[0239]

[0240] After dissolving Sub1-37 (11.8 g, 20.7 mmol) in toluene (82 mL), Sub2-46 (4.9 g, 20.7 mmol), Pd2(dba)3 (0.6 g, 0.6 mmol), Xphos (4.9 g, 10.4 mmol), and NaOt-Bu (4.0 g, 41.5 mmol) were added, and the same method as the synthesis example of P-15 was followed to obtain 11.0 g of the product (yield: 73%).

[0241] 4. P-81 synthetic example

[0242]

[0243] After dissolving Sub1-61 (10.2 g, 14.8 mmol) in toluene (74 mL), Sub2-25 (3.6 g, 14.8 mmol), Pd2(dba)3 (0.4 g, 0.4 mmol), Xphos (3.5 g, 7.4 mmol), and NaOt-Bu (2.8 g, 29.7 mmol) were added, and the synthesis was carried out in the same manner as in the synthesis example of P-15, to obtain 10.2 g of the product (yield: 71%).

[0244] 5. P-108 Synthetic Example

[0245]

[0246] After dissolving Sub1-80 (10.6 g, 20.5 mmol) in toluene (74 mL), Sub2-2 (4.8 g, 20.5 mmol), Pd2(dba)3 (0.6 g, 0.6 mmol), Xphos (4.9 g, 10.3 mmol), and NaOt-Bu (3.9 g, 41.1 mmol) were added, and the same method as the synthesis example of P-15 was followed to obtain 10.3 g of the product (yield: 75%).

[0247] The FD-MS values ​​of compounds P-1 to P-108 of the present invention manufactured according to the above synthetic examples are as shown in Table 3 below.

[0248] Compound FD-MS Compound FD-MSP-1 m / z=639.29 (C 49 H 37 N=693.84)P-2m / z=653.31 (C 53 H 39 N=653.87)P-3m / z=721.37 (C 55 H 47 N=721.99)P-4m / z=759.39 (C 58 H 49 N=760.04)P-5m / z=803.45 (C 61 H 57 N=804.13)P-6m / z=722.37 (C55 H 34 D7N=722.98)P-7m / z=803.36 (C 62 H 45 N=804.05)P-8m / z=709.37 (C 54 H 47 N=709.98)P-9m / z=659.36 (C 50 H 45 N=659.92)P-10m / z=703.32 (C 54 H 41 N=703.93)P-11m / z=729.34 (C 56 H 43 N=729.97)P-12m / z=653.31 (C 50 H 39 N=653.87)P-13m / z=743.36 (C 57 H 45 N=743.99)P-14m / z=763.32 (C 59 H 41 N=763.98)P-15m / z=671.36 (C 51 H 45 N=671.93)P-16m / z=817.37 (C 63 H 47 N=818.08)P-17m / z=789.43 (C 60 H 55 N=790.11)P-18m / z=779.36 (C 60 H 45 N=780.03)P-19m / z=769.36 (C 59 H 39 D4N=770.02)P-20m / z=779.36 (C 60 H 45 N=780.03)P-21m / z=747.39 (C 57 H 49 N=748.03)P-22m / z=715.32 (C 55 H 41 N=715.94)P-23m / z=769.37 (C 59 H 47 N=770.03)P-24m / z=791.36 (C 61 H 45N=792.04)P-25m / z=805.37 (C 62 H 47 N=806.06)P-26m / z=849.38 (C 63 H 51 NSi=850.19)P-27m / z=653.31 (C 50 H 39 N=653.87)P-28m / z=797.40 (C 61 H 51 N=798.09)P-29m / z=701.40 (C 53 H 51 N=702.00)P-30m / z=723.39 (C 55 H 49 N=724.00)P-31m / z=695.36 (C 53 H 45 N=695.95)P-32m / z=809.40 (C 62 H 51 N=810.10)P-33m / z=776.42 (C 59 H 44 D5N=777.08)P-34m / z=797.40 (C 61 H 51 N=798.09)P-35m / z=742.33 (C 56 H 42 N2=742.97)P-36m / z=729.34 (C 56 H 43 N=729.97)P-37m / z=730.33 (C 55 H 42 N2=730.95)P-38m / z=695.36 (C 53 H 45 N=695.95)P-39m / z=737.29 (C 51 H 38 F3NO=737.87)P-40m / z=775.32 (C 60 H 41 N=775.99)P-41m / z=793.37 (C 61 H 47 N=794.05)P-42m / z=845.40 (C 65 H 51 N=846.13)P-43m / z=653.31 (C 50H 39 N=653.87)P-44m / z=775.32 (C 60 H 41 N=775.99)P-45m / z=864.35 (C 66 H 44 N2=865.09)P-46m / z=728.32 (C 55 H 40 N2=728.94)P-47m / z=818.37 (C 62 H 46 N2=819.06)P-48m / z=803.45 (C 61 H 57 N=804.13)P-49m / z=670.34 (C 51 H 38 D3N=670.91)P-50m / z=743.36 (C 57 H 45 N=743.99)P-51m / z=867.39 (C 67 H 49 N=868.14)P-52m / z=867.39 (C 67 H 49 N=868.124)P-53m / z=789.34 (C 61 H 43 N=790.02)P-54m / z=725.39 (C 55 H 31 D 10 N=726.00)P-55m / z=873.41 (C 66 H 43 D5N2=874.15)P-56m / z=657.33 (C 50 H 35 D4N=657.89)P-57m / z=653.31 (C 50 H 39 N=653.87)P-58m / z=725.40 (C 55 H 43 D4N=726.01)P-59m / z=715.32 (C 55 H 41 N=715.94)P-60m / z=720.36 (C 55 H 36 D5N=720.97)P-61m / z=743.36 (C 57 H 45N=743.99)P-62m / z=949.37 (C 71 H 51 NS=950.26)P-63m / z=715.32 (C 55 H 41 N=715.94)P-64m / z=881.40 (C 68 H 51 N=882.16)P-65m / z=851.36 (C 66 H 45 N=852.09)P-66m / z=733.37 (C 56 H 47 N=734.00)P-67m / z=867.39 (C 67 H 49 N=868.14)P-68m / z=783.39 (C 60 H 49 N=784.06)P-69m / z=693.33 (C 53 H 35 D4N=693.93)P-70m / z=779.36 (C 60 H 45 N=780.03)P-71m / z=821.40 (C 63 H 51 N=822.11)P-72m / z=721.37 (C 55 H 47 N=721.99)P-73m / z=847.42 (C 65 H 53 N=848.15)P-74m / z=669.34 (C 51 H 43 N=669.91)P-75m / z=791.36 (C 61 H 45 N=792.04)P-76m / z=729.34 (C 56 H 43 N=729.97)P-77m / z=773.40 (C 59 H 51 N=774.06)P-78m / z=837.34 (C 65 H 43 N=838.07)P-79m / z=779.36 (C 60 H 45 N=780.03)P-80m / z=729.34 (C 56 H43 N=729.97)P-81m / z=845.40 (C 65 H 51 N=846.13)P-82m / z=841.37 (C 65 H 47 N=842.10)P-83m / z=709.37 (C 54 H 47 N=709.98)P-84m / z=853.33 (C 65 H 43 NO=854.06)P-85m / z=715.32 (C 55 H 41 N=715.94)P-86m / z=885.53 (C 67 H 67 N=886.28)P-87m / z=831.48 (C 63 H 61 N=832.19)P-88m / z=779.36 (C 60 H 45 N=780.03)P-89m / z=806.37 (C 61 H 46 N2=807.05)P-90m / z=745.37 (C 57 H 47 N=746.01)P-91m / z=657.33 (C 50 H 35 D4N=657.89)P-92m / z=920.42 (C 71 H 44 D5N=921.21)P-93m / z=1001.50 (C 77 H 63 N=1002.36)P-94m / z=844.38 (C 64 H 48 N2=845.10)P-95m / z=958.43 (C 74 H 46 D5N=959.26)P-96m / z=860.41 (C 65 H 52 N2=861.14)P-97m / z=879.43 (C 65 H 57 NSi=880.26)P-98m / z=897.38 (C 67 H 51NSi=898.24)P-99m / z=840.44 (C 63 H 56 N2=841.15)P-100m / z=717.31 (C 53 H 39 N3=717.92)P-101m / z=745.37 (C 57 H 47 N=746.01)P-102m / z=711.39 (C 54 H 49 N=711.99)P-103m / z=926.37 (C 71 H 46 N2=927.16)P-104m / z=857.50 (C 65 H 63 N=858.23)P-105m / z=663.44 (C 49 H 13 D 24 N=663.99)P-106m / z=785.40 (C 60 H 51 N=786.08)P-107m / z=765.34 (C 59 H 43 N=766.00)P-108m / z=667.32 (C 51 H 41 N=667.90)

[0249] Although the above has been described with regard to synthetic examples of the compound represented by Chemical Formula 1, these are all based on Buchwald-Hartwig cross coupling reaction, Miyaura boration reaction, Suzuki cross-coupling reaction, Intramolecular acid-induced cyclization reaction (J. mater. Chem. 1999, 9, 2095), Pd(II)-catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504), and PPh3-mediated reductive cyclization reaction (J. Org. Chem. 2005, 70, 5014), and those skilled in the art will easily understand that the above reaction proceeds even if a substituent other than the substituent specified in the specific synthetic example is combined with another substituent defined in Chemical Formula 1.

[0250] Manufacturing and evaluation of organic electronic devices

[0251] [Example 1] Green organic light-emitting device (hole transport layer)

[0252] A hole injection layer having a thickness of 10 nm is formed by vacuum-depositing the compound P-1 of the present invention and 4,4',4''-((1E,1'E,1''E)-cyclopropane-1,2,3-triylidenetris(cyanomethaneylylidene))tris(2,3,5,6-tetrafluorobenzonitrile) on an ITO layer (anode) formed on a glass substrate. At this time, the compound A of the present invention is doped so that the weight ratio of the compound P-1 and 4,4',4"-((1E,1'E,1"E)-cyclopropane-1,2,3-triylidenetris(cyanomethaneylylidene))tris(2,3,5,6-tetrafluorobenzonitrile) (hereinafter referred to as compound A) is 98:2.

[0253] Thereafter, the compound P-1 of the present invention is vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 110 nm.

[0254] Afterwards, N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amine is vacuum-deposited on the hole transport layer to form a light-emitting auxiliary layer with a thickness of 10 nm.

[0255] Thereafter, a host 5-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-7,7-dimethyl-5,7-dihydroindeno[2,1-b]carbazole and a dopant tris(2-phenylpyridine)-iridium are vacuum-deposited on the light-emitting auxiliary layer to form a light-emitting layer with a thickness of 30 nm. At this time, the dopant is doped so that the weight ratio of the host and the dopant becomes 90:10.

[0256] Afterwards, 2-(4'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine is vacuum-deposited on the light-emitting layer to form a hole-blocking layer.

[0257] Afterwards, a mixture of 2,7-bis(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalene and (8-quinolinolato)lithium in a weight ratio of 5:5 is vacuum-deposited on the hole-blocking layer to form an electron transport layer with a thickness of 30 nm.

[0258] Afterwards, 8-quinolinolato)lithium is deposited on the electron transport layer to form an electron injection layer with a thickness of 0.2 nm, and then Al is deposited to form a cathode with a thickness of 150 nm.

[0259] [Example 2] to [Example 15]

[0260] An organic light-emitting device was manufactured in the same manner as Example 1, except that the compound of the present invention described in Table 4 below was used instead of the compound P-1 of the present invention as a hole transport layer material.

[0261] [Comparative Example 1] and [Comparative Example 2]

[0262] An organic light-emitting device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 or Comparative Compound 2 was used instead of Compound P-1 of the present invention as a hole transport layer material.

[0263] Comparative Compound 1 Comparative Compound 2

[0264]

[0265] The organic electroluminescence devices manufactured by Examples 1 to 15 of the present invention and Comparative Examples 1 and 2 were subjected to a forward bias DC voltage, and the electroluminescence (EL) characteristics were measured using PR-650 from Photoresearch, and 5000 cd / m 2 T95 was measured using a life-span measuring device manufactured by Maxscience at a reference luminance. The measurement results are shown in Table 4 below.

[0266] These measuring devices are unaffected by daily variations in deposition rate, vacuum quality, or other parameters, and can evaluate new performance compared to reference compounds under identical conditions. Since each batch contains four identically prepared OLEDs containing the reference compound, and the performance of a total of 12 OLEDs is evaluated in three batches, the experimental results obtained in this manner are statistically significant.

[0267] Compound driving voltage (V) Current density (mA / cm) 2 ) Luminance (cd / m 2)Efficiency (cd / A)Lifetime T (95)Comparative Example 1Comparative Compound 15.311.85000.042.486.8Comparative Example 2Comparative Compound 25.112.55000.040.186.0Example 1P-14.49.35000.053.9118.4Example 2P-24.39.35000.053.9118.0Example 3P-64.49.75000.051.6117.5Example 4P-84.49.35000.054.0112.0Example 5P-124.49.55000.052.7113.0Example 6P-204.49.75000.051.5113.7 Example 7P-294.49.85000.051.1118.3 Example 8P-334.59.45000.052.9110.5 Example 9P-424.69.85000.050.8110.8 Example 10P-534.59.95000.050.5112.5 Example 11P-684.59.85000.051.3113.5 Example 12P-734.49.65000.051.9113.0 Example 13P-744.39.55000.052.7111.9 Example 14P-1054.49.35000.053.8116.1 Example 15P-1064.39.65000.051.9110.4

[0268] From the above Table 4, it can be seen that when the compound of the present invention is used as a hole transport layer material, the driving voltage of the organic light emitting device can be lowered and the luminous efficiency and lifespan can be significantly improved compared to when Comparative Compound 1 or Comparative Compound 2 having a similar skeleton is used. The compound of Chemical Formula 1 of the present invention includes a 'phenyl-phenyl-naphthyl' moiety as one of the substituents of the amine group substituted on the fluorene skeleton, and naphthyl and phenyl are bonded to each other in a para position to the phenyl directly bonded to the nitrogen of the amine group, and R substituted on the naphthyl 8 It is characterized by the fact that adjacent groups cannot form rings.

[0269] Comparative compounds 1 and 2 are also similar to the compounds of the present invention in that they have a structure in which an amine group is substituted on a fluorene skeleton. However, Comparative compound 1 differs in that among the substituents of the amine group, phenyl and naphthyl are bonded in the meta position in the 'phenyl-phenyl-naphthyl' substituent, and Comparative compound 2 differs in that pyrene, not naphthyl, is substituted.

[0270] When the compound of the present invention is used as a material for a hole transport layer compared to Comparative Compound 2, the driving voltage is improved while the efficiency and lifespan are significantly improved. This appears to be because the energy level of the compound varies depending on the type of substituent.

[0271] Table 5 below shows the HOMO values ​​of comparative compound 2 and compound P-1 of the present invention.

[0272] Comparative compound 2P-1HOMO (eV) -4.820-4.781

[0273] From the above Table 5, it can be seen that the HOMO value of the compound of the present invention is large, and since the HOMO value is large, hole transfer from the hole transport layer to the light-emitting layer is faster and smoother, thereby improving the charge balance in the light-emitting layer, reducing the interfacial luminescence between the light-emitting auxiliary layer and the light-emitting layer, and as a result of mainly luminescence occurring within the light-emitting layer, it appears that the overall performance of the device is improved. Therefore, even if it is a compound with a similar structure, it can be confirmed that the compound of the present invention, which satisfies all complex factors such as the presence or absence of a substituent, the type, and the substitution position of the substituent, exhibits a remarkable effect compared to other comparative compounds in an organic electric device, and through this, it can be seen that the compound of the present invention exhibits a remarkable effect in an organic electric device compared to other compounds with a similar structure not described in the present specification.

[0274] Through this, it can be seen that even if a compound with a similar structure is used as a hole transport layer material, the properties of the compound, such as the hole characteristics of the molecule, light efficiency characteristics, energy level, hole injection and mobility characteristics, charge balance of holes and electrons, volume density, and intermolecular distance, can differ depending on the presence or absence, type, and substitution position of the substituent, and that the performance of the device can differ significantly due to these differences.

[0275] In addition, in the case of the hole transport layer, the relationship with the light-emitting layer must be understood, and even if it is a compound with a similar composition, it would be very difficult for a person skilled in the art to infer the characteristics that appear when the compound according to the present invention is used as a hole transport layer material.

[0276] In the evaluation results of the above-described device fabrication, the device characteristics in which the compound of the present invention is applied to only one layer of the hole transport layer have been described, but the compound of the present invention may also be applied to both the hole transport layer and the light-emitting auxiliary layer.

[0277] The above description is merely illustrative of the present invention. Those skilled in the art will appreciate that various modifications may be made without departing from the essential characteristics of the present invention. The scope of protection of the present invention should be construed in accordance with the claims below, and all techniques within the scope equivalent thereto should be construed as being included within the scope of the present invention.

Claims

1. A compound represented by the following chemical formula 1: <Chemical formula 1> In the above chemical formula 1, Ar 1 Silver C 6 ~C 60 Aryl group of; Fluorenyl group; C containing at least one heteroatom among O, N, S, Si and P 2 ~C 60 Heterocyclic group of ; C 3 ~C 60 Aliphatic ring of; C 3 ~C 60 Aliphatic ring and C 6 ~C 60 Fused ring group of aromatic ring; C 1 ~C 30 An alkyl group; and a silane group are selected from the group consisting of, R 1 and R 2 are independent of each other C 6 ~C 60 Aryl group of; Fluorenyl group; C containing at least one heteroatom among O, N, S, Si and P 2 ~C 60 Heterocyclic group of ; C 3 ~C 60 Aliphatic ring group of; C 3 ~C 60 Aliphatic ring and C 6 ~C 60 A fused ring group of an aromatic ring; and C 1 ~C 30 is selected from the group consisting of alkyl groups, R 1 and R 2 can combine with each other to form rings, R 3 Inland R 8 are independently hydrogen; deuterium; halogen; cyano group; nitro group; C 6 ~C 60 Aryl group of; Fluorenyl group; C containing at least one heteroatom among O, N, S, Si and P 2 ~C 60 Heterocyclic group of ; C 3 ~C 60 Aliphatic ring of; C 6 ~C 60 Aromatic ring of C 3 ~C 60 A fused ring group of aliphatic rings; C 1 ~C 20 alkyl group of; and silane group, and is selected from the group consisting of adjacent R 3 Kiri, neighboring R 4 Kiri, neighboring R 6 Kiri, neighboring R 7 They can combine with each other to form rings, a and c are each an integer from 0 to 4, b is an integer from 0 to 3, d is each an integer from 0 to 5, e is an integer from 0 to 3, f is an integer from 0 to 7, The above aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, silane group, and ring formed by bonding adjacent groups to each other are each composed of deuterium; halogen; C 1 -C 20 Alkyl group of or C 6 -C 20 Silane group substituted or unsubstituted with an aryl group; C 1 -C 20 Alkyl group of or C 6 -C 20 Phosphine oxide substituted or unsubstituted with an aryl group; Cyano group; Nitro group; C 1 -C 20 Alkylthio group of; C 1 -C 20 Alkoxy group of; C 6 -C 30 Arylcyogi of; C 6 -C 30 Aryloxy group of; C 1 -C 20 Alkyl group of ; C 2 -C 20 Alkenyl group of ; C 2 -C 20 Alkyne group of ; C 6 -C 30 Aryl group of; Fluorenyl group; C containing at least one heteroatom among O, N, S, Si and P 2 -C 30 Heterocyclic group of ; C 3 -C 30 aliphatic ring group; and C 6 -C 30 Aromatic ring of C 3 -C 30 It can be substituted with one or more substituents selected from the group consisting of a fused ring group of an aliphatic ring, and adjacent substituents can be combined with each other to form a ring, and the hydrogen of the substituent can be replaced with deuterium.

2. In paragraph 1, The above chemical formula 1 is a compound characterized by being represented by the following chemical formula 1-1 or chemical formula 1-2: <Chemical Formula 1-1> <Chemical Formula 1-2> In the above chemical formulas 1-1 and 1-2, Ar 1 , R 3 Inland R 8 , a to f are as defined in paragraph 1, and the hydrogen of the methyl group of the 9,9-dimethyl-9H-fluorenyl group can be replaced with deuterium.

3. In paragraph 1, The above chemical formula 1 is a compound characterized by being represented by the following chemical formula 1-3 or chemical formula 1-4: <Chemical Formula 1-3> <Chemical Formula 1-4> In the above chemical formulas 1-1 and 1-4, Ar 1 , R 3 Inland R 8 , a to f are as defined in clause 1, and R 3' is R of Article 1 3 is defined identically to R 4' is R of Article 1 4 is defined identically to R, except that 3' Wow R 4' Except when it is hydrogen, the hydrogen of the methyl group of 9,9-dimethyl-9H-fluorenyl group can be replaced with deuterium.

4. In paragraph 1, Ar 1 A compound characterized by being selected from the group consisting of the following chemical formulas Ar-1 to Ar-5: <Chemical formula Ar-1> <Chemical formula Ar-2> <Chemical formula Ar-3> <Chemical formula Ar-4> <Chemical formula Ar-5> In the above chemical formulas Ar-1 to Ar-5, L 1 is a single bond; C 6 ~C 60 Arylene group of; Fluorenylene group; C containing at least one heteroatom among O, N, S, Si and P 2 ~C 60 Heterocyclic group of ; C 3 ~C 60 Aliphatic ring group of; C 3 ~C 60 Aliphatic ring and C 6 ~C 60 Fused ring group of aromatic ring; C 1 ~C 30 alkylene group; and silane group, X is O, S, N(R), C(R')(R") or Si(R')(R"), R 11 Inland R 13 , R' and R" are independently hydrogen; deuterium; halogen; C 1 -C 20 Alkyl group of or C 6 -C 20 Silane group substituted or unsubstituted with an aryl group; C 1 -C 20 Alkyl group of or C 6 -C 20 Phosphine oxide substituted or unsubstituted with an aryl group; Cyano group; Nitro group; C 1 -C 20 Alkylthio group of; C 1 -C 20 Alkoxy group of; C 6 -C 30 Arylcyogi of; C 6 -C 30 Aryloxy group of; C 1 -C 20 Alkyl group of ; C 2 -C 20 Alkenyl group of ; C 2 -C 20 Alkyne group of ; C 6 -C 30 Aryl group of; Fluorenyl group; C containing at least one heteroatom among O, N, S, Si and P 2 -C 30 Heterocyclic group of ; C 3 -C 30 aliphatic ring group; and C 6 -C 30 Aromatic ring of C 3 -C 30 is selected from the group consisting of fused ring groups of aliphatic rings, and adjacent groups can combine with each other to form a ring, The above R is C 1 -C 20 Alkyl group of ; C 6 -C 30 Aryl group of; Fluorenyl group; C containing at least one heteroatom among O, N, S, Si and P 2 -C 30 Heterocyclic group of ; C 3 -C 30 aliphatic ring group; and C 6 -C 30 Aromatic ring of C 3 -C 30 is selected from the group consisting of fused ring groups of aliphatic rings, m is an integer from 0 to 5, n is an integer from 0 to 3, and o is an integer from 0 to 4.

5. In paragraph 1, A compound represented by the above chemical formula 1 is characterized in that it is one of the following compounds: .

6. In an organic electric device including a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, An organic electric device, characterized in that the organic layer comprises the compound of claim 1.

7. In paragraph 6, An organic electric device characterized in that the organic layer includes a hole transport layer, and the hole transport layer includes the compound.

8. In paragraph 6, An organic electric device characterized in that the organic layer comprises two or more stacks including a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on the first electrode.

9. In paragraph 8, An organic electric device characterized in that the organic layer further includes a charge generation layer formed between two or more stacks.

10. In paragraph 6, The organic electric element further comprises a light efficiency improvement layer, wherein the light efficiency improvement layer is formed on one surface of the first electrode or the second electrode that is not in contact with the organic layer.

11. A display device including the organic electric element of clause 6; and An electronic device including a control unit that drives the display device.

12. In paragraph 11, The above organic electric device is an electronic device selected from the group consisting of an organic light-emitting device, an organic solar cell, an organic photoconductor, an organic transistor, a monochrome lighting device, and a quantum dot display device.

13. A compound obtained by recovering and purifying the material of the organic layer from the deposition equipment after depositing the organic layer in the manufacturing process of an organic electric device. A compound characterized in that the compound is a compound represented by the chemical formula 1 of claim 1.

14. In paragraph 13, A compound characterized in that the purity of the compound is 99.9% or higher.

15. A step of depositing an organic layer material including a compound represented by the chemical formula 1 of paragraph 1; A step of recovering the organic layer material attached to the deposition equipment; and A method for recovering a compound, characterized by including a step of purifying the recovered organic layer material to obtain a compound represented by the chemical formula 1 having a purity of 99.9% or higher.

16. In paragraph 15, A method for recovering a compound, characterized in that the purification of the recovered organic layer material comprises a step of recrystallizing the recovered organic layer material using a recrystallization solvent, a step of adsorption separation using an adsorbent, and a step of sublimation purification.

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