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

Abstract

The present invention provides a novel compound that can improve the luminous efficiency, stability, and lifespan of an element, an organic electric element using same, and an electronic device having same.

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 with different materials to enhance the efficiency and stability of the device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

[0003] Materials used as organic layers in organic electronic devices can be classified according to their function into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials.

[0004] 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.

[0005] Efficiency, lifespan, and operating voltage are interrelated. As efficiency increases, the operating voltage decreases relatively. As the operating voltage decreases, the crystallization of organic substances due to Joule heating generated during operation decreases, which results in a tendency for the lifespan to increase.

[0006] However, simply improving the organic layers does not maximize efficiency. This is because long life and high efficiency can be achieved simultaneously when the energy levels and T1 values ​​between each organic layer, as well as the material's inherent properties (mobility, interfacial properties, etc.) are optimally combined.

[0007] In addition, in order to solve the problem of light emission in the hole transport layer in recent organic light emitting devices, a light emitting auxiliary layer must exist between the hole transport layer and the light emitting layer, and it is time to develop different light emitting auxiliary layers for each light emitting layer (R, G, B).

[0008] Typically, electrons are transferred from the electron transport layer to the light-emitting layer, and holes are transferred from the hole transport layer to the light-emitting layer, and excitons are generated through recombination.

[0009] However, since the material used in the hole transport layer must have a low HOMO value, most of them have a low T1 value, which causes excitons generated in the light-emitting layer to move to the hole transport layer, resulting in charge imbalance within the light-emitting layer and causing light emission at the hole transport layer interface.

[0010] When light is emitted at the interface of the hole transport layer, the color purity and efficiency of the organic electronic device are reduced, and its lifespan is shortened. Therefore, there is an urgent need to develop a light-emitting auxiliary layer with a high T1 value and a HOMO energy level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light-emitting layer.

[0011] Meanwhile, there is a need to develop a hole injection layer material that has stable properties, i.e., a high glass transition temperature, against Joule heating generated during device operation while delaying the penetration and diffusion of metal oxides from the anode electrode (ITO), which is one of the causes of shortened lifespan of organic electronic devices. The low glass transition temperature of the hole transport layer material has the characteristic of reducing the uniformity of the thin film surface during device operation, which is reported to have a significant impact on the device lifespan. In addition, OLED devices are mainly formed by a deposition method, and there is a need to develop materials that can withstand the deposition process for a long time, i.e., materials with strong heat resistance.

[0012] In other words, in order to fully demonstrate the excellent characteristics of organic electronic devices, the materials forming the organic layers within the devices, such as hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, and luminescent auxiliary layer materials, must first be supported by stable and efficient materials. However, the development of stable and efficient organic layer materials for organic electronic devices has not yet been sufficiently accomplished. Therefore, the development of new materials continues to be required, and the development of materials for luminescent auxiliary layers is particularly urgently needed.

[0013] In order to solve the problems of the above-described background technology, the present invention has discovered a compound having a novel structure, and has also discovered that when this compound is applied to an organic electric device, the luminous efficiency, stability, and lifespan of the device can be greatly improved.

[0014] Accordingly, the present invention aims to provide a novel compound, an organic electric element using the same, and an electronic device thereof.

[0015] The present invention provides a compound represented by the following chemical formula 1.

[0016] Chemical Formula 1

[0017]

[0018] 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 1.

[0019] By using the compound according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the device can be achieved, and the color purity and lifespan of the device can be greatly improved.

[0020] Figures 1 to 3 are exemplary diagrams of an organic light-emitting device according to the present invention.

[0021] Figure 4 shows a chemical formula according to one aspect of the present invention.

[0022] 100, 200, 300: Organic electric element 110: First electrode

[0023] 120: hole injection layer 130: hole transport layer

[0024] 140: Emitting layer 150: Electron transport layer

[0025] 160: Electron injection layer 170: Second electrode

[0026] 180: Light efficiency improvement layer 210: Buffer layer

[0027] 220: Light-emitting auxiliary layer 320: First hole injection layer

[0028] 330: First hole transport layer 340: First light-emitting layer

[0029] 350: First electron transport layer 360: First charge generation layer

[0030] 361: Second charge generation layer 420: Second hole injection layer

[0031] 430: Second hole transport layer 440: Second light-emitting layer

[0032] 450: Second electron transport layer CGL: Charge generation layer

[0033] ST1: First stack ST2: Second stack

[0034] Hereinafter, the present invention will be described in detail with reference to embodiments. In describing the present invention, if a detailed description of a related known configuration or function is judged to obscure the gist of the present invention, such detailed description will be omitted.

[0035] Additionally, terms such as first, second, A, B, (a), (b), etc. may be used to describe components of the present invention. 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.

[0036] As used in this specification and the appended claims, unless otherwise stated, the following terms have the following meanings:

[0037] The term “halo” or “halogen” as used herein, unless otherwise stated, means fluorine (F), bromine (Br), chlorine (Cl), or iodine (I).

[0038] The term "alkyl" or "alkyl group" as used in the present invention, unless otherwise stated, means a radical of a saturated aliphatic functional group having a single bond of 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms, or 1 to 12 carbon atoms, including a straight-chain alkyl group, a branched-chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cycloalkyl group, or a cycloalkyl-substituted alkyl group.

[0039] The term "alkenyl group", "alkenyl group" or "alkynyl group" used in the present invention, unless otherwise stated, includes a straight-chain or branched chain group having a double bond or triple bond of 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 18 carbon atoms or 2 to 12 carbon atoms, but is not limited thereto.

[0040] The term "cycloalkyl" or "cycloalkyl" as used in the present invention means, unless otherwise stated, an alkyl forming a ring having 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 25 carbon atoms, 3 to 18 carbon atoms or 3 to 12 carbon atoms, but is not limited thereto.

[0041] The term “alkoxyl group,” “alkoxy group,” or “alkyloxy group” used in the present invention means an alkyl group having an oxygen radical attached thereto, and unless otherwise specified, has, but is not limited to, 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms, or 1 to 12 carbon atoms.

[0042] The term "aryloxyl group" or "aryloxy group" used in the present invention means an aryl group having an oxygen radical attached thereto, and unless otherwise specified, has, but is not limited to, 6 to 60 carbon atoms, 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms.

[0043] The terms "aryl group" and "arylene group" used in the present invention, unless otherwise stated, have, but are not limited to, 6 to 60 carbon atoms, 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms, respectively. In the present invention, the aryl group or arylene group refers to a single ring or multi-ring aromatic group, and includes an aromatic ring formed by the participation of adjacent substituents in a bond or reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

[0044] The prefix "aryl" or "ar" refers to a radical substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, an arylalkenyl group is an alkenyl group substituted with an aryl group, and the aryl-substituted radical has the number of carbon atoms described herein.

[0045] Also, when prefixes are named consecutively, it means that the substituents are listed in the order they were first written. For example, in the case of arylalkoxy group, it means an alkoxy group substituted with an aryl group, in the case of alkoxylcarbonyl group, it means a carbonyl group substituted with an alkoxyl group, and in the case of arylcarbonylalkenyl group, it means an alkenyl group substituted with an arylcarbonyl group, where the arylcarbonyl group is a carbonyl group substituted with an aryl group.

[0046] The term "heterocyclic group" used in the present invention, unless otherwise stated, includes one or more heteroatoms, has 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 18 carbon atoms, or 2 to 12 carbon atoms, includes at least one of a single ring and a multiple ring, and includes a heteroaliphatic ring and a heteroaromatic ring. It may also be formed by bonding adjacent functional groups.

[0047] The term “heteroatom” as used herein refers to N, O, S, P or Si unless otherwise stated.

[0048] Additionally, the term "heterocyclic group" refers to a single ring, a ring aggregate, a fused multiple ring system, a spiro compound, etc. containing a heteroatom. In addition, compounds containing a heteroatom group such as SO2, P=O, etc. instead of carbon forming a ring, such as the compounds below, may also be included in the heterocyclic group. For example, the term "heterocyclic group" includes the following compounds.

[0049]

[0050] The term "aliphatic ring" used in the present invention means a cyclic hydrocarbon other than an aromatic hydrocarbon, and includes a single ring, a ring aggregate, a fused multiple ring system, a spiro compound, etc., and unless otherwise specified, means a ring having 3 to 60 carbon atoms, a ring having 3 to 30 carbon atoms, a ring having 3 to 25 carbon atoms, a ring having 3 to 18 carbon atoms, or a ring having 3 to 12 carbon atoms, but is not limited thereto. For example, even when an aromatic ring, benzene, and a non-aromatic ring, cyclohexane, are fused, it is considered an aliphatic ring.

[0051] The term "fluorenyl group", "fluorenylene group" or "fluorenetriyl group" used in the present invention, unless otherwise stated, means a monovalent, divalent or trivalent functional group in which R, R' and R" in the structure below are all hydrogen, and a "substituted fluorenyl group", "substituted fluorenylene group" or "substituted fluorenetriyl group" means that at least one of the substituents R, R' and R" is a substituent other than hydrogen, and includes a case where R and R' are bonded to each other to form a spiro compound together with the carbon to which they are bonded. In the present specification, regardless of valence, a fluorenyl group, a fluorenylene group and a fluorenetriyl group may all be referred to as a fluorene group.

[0052]

[0053] The term "spiro compound" used in the present invention has a "spiro union," and a spiro union means a connection formed by two rings sharing only one atom. In this case, 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.

[0054] Unless otherwise stated, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms or 1 to 12 carbon atoms, and "aliphatic ring" means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 25 carbon atoms, 3 to 18 carbon atoms or 3 to 12 carbon atoms.

[0055] Unless otherwise stated, the term "ring" as used herein means an aliphatic ring having 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 25 carbon atoms, 3 to 18 carbon atoms, or 3 to 12 carbon atoms; or an aromatic ring having 6 to 60 carbon atoms, 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms; or a heterocycle having 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 18 carbon atoms, or 2 to 12 carbon atoms; or a fused ring composed of a combination thereof, including a saturated or unsaturated ring.

[0056] Other heterocyclic compounds or heteroradicals other than the aforementioned heterocyclic compounds include, but are not limited to, one or more heteroatoms.

[0057] Also, unless explicitly stated otherwise, the term "substituted" in the term "substituted or unsubstituted" used in the present invention means deuterium, halogen, amino group, nitrile group, nitro group, C1~C 20 Alkyl group of C1~C 20 Alkoxyl group, C1~C 20 Alkylamine group of C1~C 20 Alkylthiophene group, C6~C 20 Arylthiophene group, C2~C 20 Alkenyl group, C2~C 20 Alkyne group, C3~C 20 Cycloalkyl group of C6~C 20 Aryl group of C6~C substituted with deuterium20 Aryl group of C8~C 20 Arylalkenyl group, silane group, boron group, germanium group, and C2~C 20 It means that it is substituted with one or more substituents selected from the group consisting of heterocyclic groups, but is not limited to these substituents.

[0058] 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', but may also 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, but it may also 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. In addition, in this specification, numbers or alphabets indicating positions may be omitted when describing the compound name or substituent name. For example, pyrido[4,3-d]pyrimidine can be written as pyridopyrimidine, benzofuro[2,3-d]pyrimidine can be written as benzofuropyrimidine, 9,9-dimethyl-9H-fluorene can be written as dimethylfluorene, etc. Accordingly, both benzo[g]quinoxaline and benzo[f]quinoxaline can be written as benzoquinoxaline.

[0059] 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.

[0060]

[0061] Here, if a is an integer of 0, the substituent R 1 is absent, and if a is an integer of 1, there is one substituent R 1is bonded to one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it is bonded as follows, in which case R 1 may be the same or different, and when a is an integer from 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the indication of the hydrogen bonded to the carbon forming the benzene ring is omitted.

[0062]

[0063] In addition, unless explicitly stated otherwise, the terms "ortho", "meta", and "para" used in the present invention mean the substitution positions of all substituents, and the ortho position refers to a compound in which the positions of the substituents are immediately adjacent, for example, in the case of benzene, it refers to the 1st and 2nd positions, the meta position refers to the substitution position next to the immediately adjacent substitution position, and refers to the 1st and 3rd positions in the case of benzene as an example, and the para position refers to the substitution position next to the meta position, and refers to the 1st and 4th positions in the case of benzene as an example. A more detailed description of examples of substitution positions is as follows, and it can be confirmed that the ortho- and meta- positions are substituted in a non-linear type, and the para- position is substituted in a linear type.

[0064] [Example of ortho-position]

[0065]

[0066] [Example of meta-position]

[0067]

[0068] [Example of para-location]

[0069]

[0070]

[0071] Hereinafter, a compound according to one aspect of the present invention and an organic electric device including the same will be described.

[0072] The present invention provides a compound represented by the following chemical formula 1.

[0073] Chemical Formula 1

[0074]

[0075] In the above chemical formula 1, each symbol can be defined as follows.

[0076] L 1 and L 2 are independently of each other and are single bonds; C6~C 60 C2~C containing an arylene group; a fluorenylene group; and at least one heteroatom selected from O, N, S, Si, and P 60 is selected from the group consisting of heterocyclic groups;

[0077] Above L 1 and L 2 If it is an arylene group, preferably C6~C 30 Arylene group, more preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an arylene group, such as phenylene, biphenylene, naphthylene, terphenylene, anthracenylene, phenanthrenylene, etc.

[0078] Above L 1 and L 2 If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0079] Ar 1 and Ar 2 are independently C6~C 60 C2~C containing an aryl group; a fluorenyl group; and at least one heteroatom selected from O, N, S, Si, and P 60 is selected from the group consisting of heterocyclic groups;

[0080] The above Ar 1 and Ar 2 If it is an aryl group, preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, chrysene, etc.

[0081] The above Ar 1 and Ar 2 If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0082] R a and R b 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; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C20 Alkynyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 is selected from the group consisting of aryloxy group of R; or a and R b can combine with each other to form a spirobifluorene group,

[0083] The above R a and R b If it is an aryl group, preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, chrysene, etc.

[0084] The above R a and R b If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0085] The above R a and R b If it is an alkyl group, preferably C1~C 30 It may be an alkyl group of, more preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0086] The above R a and R b If it is an alkoxyl group, preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkoxyl group.

[0087] The above R a and R b If it is an aryloxy group, preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an aryloxy group.

[0088] R 1 and R 2 are identical or different from each other, and independently of each other, hydrogen; deuterium; 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 and C6~C 60 Fused ring group of aromatic ring; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 An aryloxy group of R is selected from the group consisting of, or a plurality of adjacent R 1 R's or multiple R's 2 They can combine with each other to form rings,

[0089] The above R 1 and R 2 If it is an aryl group, preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, chrysene, etc.

[0090] The above R 1 and R 2 If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0091] The above R 1 and R 2 If it is a fusion ring, preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 25 Aliphatic ring and C6~C 25 It may be a fused ring group of an aromatic ring.

[0092] The above R 1 and R 2 If it is an alkyl group, preferably C1~C 30 It may be an alkyl group of, more preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0093] The above R 1 and R 2 If it is an alkoxyl group, preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkoxyl group.

[0094] The above R1 and R 2 If it is an aryloxy group, preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an aryloxy group.

[0095] a is an integer from 0 to 4, b is an integer from 0 to 2,

[0096] Ar a is C6~C 60 Arylene group of; and preferably C6~C 30 Arylene group, more preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an arylene group, such as phenylene, biphenylene, naphthylene, terphenylene, anthracenylene, phenanthrenylene, etc.

[0097] Ak is C1~C 50 alkyl group of; or C3~C 60 is an aliphatic ring;

[0098] If the above Ak is an alkyl group, preferably C1~C 30 It may be an alkyl group of, more preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0099] If the above Ak is an aliphatic ring group, preferably C3~C 30 aliphatic ring, more preferably C3~C 25 , C3~C 18 or C3~C 12 It may be an aliphatic ring group, and specifically, it may be cyclobutane, cyclopentane, cyclohexane, bicycloheptane, adamantyl, etc.

[0100] Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 Alkylthio group of; C1~C 20 Alkoxyl group of; C6~C 20 Aryloxy group of; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkyne group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 Aryl group of; Fluorenyl group; C2~C 20 Heterocyclic group of; C3~C 20 Aliphatic ring group; C7~C 20 Arylalkyl group of; C8~C 20 Aryl alkenyl group of; and C7~C 20 It may be further substituted with one or more substituents selected from the group consisting of alkylaryl groups; and further, the hydrogen of these substituents may be further substituted with one or more deuteriums, and further, these substituents may be combined with each other to form a ring, wherein the 'ring' means C3~C 60 Aliphatic ring or C6~C 60 Aromatic ring or C2~C 60 It refers to a fused ring composed of a heterocycle or a combination thereof, and includes a saturated or unsaturated ring.

[0101] In addition, the present invention comprises the Ar 1 or Ar 2 One of which is at least one C1~C 20 alkyl group of; or C3~C 20 Includes compounds substituted with an aliphatic ring group.

[0102] In addition, the present invention includes a compound represented by the following chemical formula 1-1.

[0103] Chemical Formula 1-1

[0104]

[0105] In the above chemical formula 1-1, each symbol can be defined as follows.

[0106] R a , R b , R 1 , R 2 , a, b, Ar a , Ak, L 1 , L 2 and Ar 2 is the same as defined in the above chemical formula 1,

[0107] Ar 3 Silver C6~C 60 Arylene group of; or C2~C containing at least one heteroatom among O, N, S, Si and P 60 is a heterocyclic group; and

[0108] The above Ar 3 If it is an arylene group, preferably C6~C 30 Arylene group, more preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an arylene group, such as phenylene, biphenylene, naphthylene, terphenylene, anthracenylene, phenanthrenylene, etc.

[0109] The above Ar 3 If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C 12It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0110] Ak 2 is C1~C 20 alkyl group of; or C3~C 20 is a fatty acid ring;

[0111]

[0112] The above chemical formula 1 can preferably be represented by the following chemical formula 1-2.

[0113] Chemical Formula 1-2

[0114]

[0115] {In the above chemical formula 1-2,

[0116] R a , R b , R 1 , R 2 , a, b, Ar a , Ak, L 1 , L 2 and Ar 1 is the same as defined in the above chemical formula 1,

[0117] R 3 and R 4 are identical or different from each other, and independently of each other, hydrogen; deuterium; C1~C 20 Alkoxyl group of; C6~C 20 Aryloxy group of; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkyne group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 20Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 20 Heterocyclic group of; C3~C 20 Aliphatic ring and C6~C 20 A fused ring group of an aromatic ring; and C3~C 20 is selected from the group consisting of aliphatic rings;

[0118] c is an integer from 0 to 3, d is an integer from 0 to 4,

[0119] X is O, S, CR 5 R 6 or SiR 5 R 6 and,

[0120] R 5 and R 6 are independently C6~C 20 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 20 Heterocyclic group of; C3~C 20 Aliphatic ring and C6~C 20 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 Alkoxyl group of; and C6~C 20 is selected from the group consisting of aryloxy group of R, or 5 and R 6 These can be combined to form rings.

[0121]

[0122] In addition, the present invention includes a compound represented by any one of the following chemical formulae Ak-1 to Ak-8.

[0123] Chemical formula Ak-1 Chemical formula Ak-2 Chemical formula Ak-3 Chemical formula Ak-4

[0124]

[0125] Chemical formula Ak-5 Chemical formula Ak-6 Chemical formula Ak-7 Chemical formula Ak-8

[0126]

[0127] {In the above chemical formulas Ak-1 to Ak-8,

[0128] * indicates the position where it is combined,

[0129] The above chemical formulas Ak-1 to Ak-8 may be further substituted with one or more deuterium atoms.

[0130]

[0131] In addition, the present invention comprises the Ar 1 or Ar 2 One of them includes a compound represented by any one of the following chemical formulas Ar-1 to Ar-11.

[0132] Chemical formula Ar-1 Chemical formula Ar-2 Chemical formula Ar-3 Chemical formula Ar-4

[0133]

[0134] Chemical formula Ar-5 Chemical formula Ar-6 Chemical formula Ar-7

[0135]

[0136] Chemical formula Ar-8 Chemical formula Ar-9 Chemical formula Ar-10

[0137]

[0138] Chemical formula Ar-11

[0139]

[0140] In the above chemical formulas Ar-1 to Ar-11, each symbol can be defined as follows.

[0141] R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14, R 15 , R 16 and R 17 are identical or different from each other, and independently of each other, hydrogen; deuterium; C6~C 20 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 20 Heterocyclic group of; C3~C 20 Aliphatic ring group; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 20 Alkoxyl group of; and C6~C 20 is selected from the group consisting of aryloxy groups; or a plurality of adjacent groups can be combined with each other to form a ring,

[0142] R c is C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C6~C 60 C2~C containing an aryl group of; and at least one heteroatom of O, N, S, Si and P 60 is selected from the group consisting of heterocyclic groups;

[0143] R d is hydrogen; deuterium; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C6~C 60 C2~C containing an aryl group of; and at least one heteroatom of O, N, S, Si and P 60 is selected from the group consisting of heterocyclic groups;

[0144] The above R c and R d If it is an alkyl group, preferably C1~C 30 It may be an alkyl group of, more preferably C1~C 25 , C1~C 18 or C1~C 12It may be an alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0145] The above R c and R d If it is an aryl group, preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, chrysene, etc.

[0146] The above R c and R d If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0147] R c and R d can combine with each other to form spiro rings,

[0148] g is an integer from 0 to 5, h, k, l, o, p and q are each independently an integer from 0 to 4, i is an integer from 0 to 7, j is an integer from 0 to 9, m and n are each independently an integer from 0 to 3,

[0149] W is O, S, CR 27 R 28 , SiR 27 R 28or NR 29 And,

[0150] R 27 , R 28 and R 29 are independently C6~C 20 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 20 Heterocyclic group of; C3~C 20 Aliphatic ring and C6~C 20 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 Alkoxyl group of; and C6~C 20 is selected from the group consisting of aryloxy group of R; or 27 and R 28 These can be combined to form rings,

[0151] * indicates the position where it is combined.}

[0152]

[0153] In addition, the present invention comprises the Ar a , L 1 and L 2 It includes a compound selected from a single bond or any one of the following chemical formulae L-1 to L-27.

[0154] [Chemical Formula L-1] [Chemical Formula L-2] [Chemical Formula L-3] [Chemical Formula L-4]

[0155]

[0156] [Chemical Formula L-5] [Chemical Formula L-6] [Chemical Formula L-7] [Chemical Formula L-8]

[0157]

[0158] [Chemical Formula L-9] [Chemical Formula L-10] [Chemical Formula L-11] [Chemical Formula L-12]

[0159]

[0160] [Chemical Formula L-13] [Chemical Formula L-14] [Chemical Formula L-15]

[0161]

[0162] [Chemical Formula L-16] [Chemical Formula L-17] [Chemical Formula L-18]

[0163]

[0164] [Chemical Formula L-19] [Chemical Formula L-20] [Chemical Formula L-21]

[0165]

[0166] [Chemical Formula L-22] [Chemical Formula L-23] [Chemical Formula L-24]

[0167]

[0168] [Chemical Formula L-25] [Chemical Formula L-26] [Chemical Formula L-27]

[0169]

[0170] {In the above chemical formulas L-1 to L-27,

[0171] Z is O, S, CR 30 R 31 or N-Ar 5 and,

[0172] R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 and R 27 Silver is the above R 7 Same as the definition of , or adjacent multiple groups can be combined to form a ring,

[0173] Ar 5 is C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C6~C 20C2~C containing an aryl group of; and at least one heteroatom of O, N, S, Si and P 20 is selected from the group consisting of heterocyclic groups;

[0174] r, t, v, w, x and y are independently integers from 0 to 4, s is an integer from 0 to 6, u is an integer from 0 to 2, z is an integer from 0 to 3, aa is an integer from 0 to 5,

[0175] * indicates the position where it is combined.}

[0176]

[0177] In addition, the present invention provides the above L 1 , L 2 , Ar 1 and Ar 2 A compound comprising at least one substituent containing deuterium.

[0178]

[0179] Specifically, the compound of the above chemical formula 1 may be any one of the following compounds P-1 to P-136, but is not limited thereto.

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215] In addition, in another aspect, the present invention provides a method for reusing a compound represented by the above chemical formula 1, including the steps of: depositing an organic light-emitting material including a compound represented by the above chemical formula 1 in a process for manufacturing an organic light-emitting device; removing impurities from an unrefined organic light-emitting material recovered from a deposition apparatus; recovering the removed impurities; and purifying the recovered impurities to a purity of 99.9% or higher.

[0216] The step of removing impurities from the crude organic light-emitting material recovered from the above deposition device may preferably include performing a preliminary purification process to obtain a purity of 98% or higher by recrystallization under a recrystallization solvent.

[0217] The above recrystallization solvent may preferably be a polar solvent having a polarity index (PI) of 5.5 to 7.2.

[0218] The above recrystallization solvent may preferably be used by mixing a polar solvent having a polarity value of 5.5 to 7.2 and a non-polar solvent having a polarity value of 2.0 to 4.7.

[0219] When the above recrystallization solvent is used by mixing a polar solvent and a non-polar solvent, the non-polar solvent may be used in a ratio of 15% (v / v) or less compared to the polar solvent.

[0220] The above recrystallization solvent is preferably a single solvent of methylpyrrolidone (N-Methylpyrrolidone; NMP); 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), dimethylacetamide, and dimethyl sulfoxide is mixed; or a single solvent selected from the group consisting of toluene, dichloromethane (DCM), dichloroethane (DCE), tetrahydrofuran (THF), chloroform, ethyl acetate, and butanone; or a mixed nonpolar solvent; Alternatively, a mixture of polar solvent and non-polar solvent can be used.

[0221] The above preliminary purification process may include a step of dissolving the crude organic light-emitting material recovered from the deposition device in a polar solvent at 90°C to 120°C and then cooling to 0°C to 5°C to precipitate crystals.

[0222] The above preliminary purification process may include a step of dissolving the crude organic light-emitting material recovered from the 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.

[0223] The above preliminary purification process may include a step of dissolving the crude organic light-emitting material recovered from the deposition device in a non-polar solvent, concentrating the solvent, and precipitating crystals while removing the non-polar solvent.

[0224] 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.

[0225] The step of purifying the recovered impurities to a purity of 99.9% or higher may include performing an adsorption separation process to adsorb and remove the impurities by adsorbing them on an adsorbent.

[0226] The above adsorbent may be activated carbon, silica gel, alumina or a material known for adsorption purposes.

[0227] The step of purifying the recovered impurities to a purity of 99.9% or higher may include performing sublimation purification.

[0228]

[0229] Referring to FIG. 1, the organic electric element (100) according to the present invention comprises a first electrode (110), a second electrode (170), and an organic layer comprising a single compound or two or more compounds represented by the chemical formula 1 between the first electrode (110) and the second electrode (170). At this time, the first electrode (110) may be an anode or positive electrode, the second electrode (170) may be a cathode or negative electrode, and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

[0230] The organic layer may sequentially include a hole injection layer (120), a hole transport layer (130), a light-emitting layer (140), an electron transport layer (150), and an electron injection layer (160) on the first electrode (110). At this time, the remaining layers except for the light-emitting layer (140) may not be formed. A hole-blocking layer, an electron-blocking layer, a light-emitting auxiliary layer (220), a buffer layer (210), etc. may be further included, and the electron transport layer (150), etc. may also function as a hole-blocking layer. (See FIG. 2)

[0231] In addition, the organic electric device according to one embodiment of the present invention may further include a protective layer or a light efficiency improvement layer (180). This light efficiency improvement layer may be formed on a surface of both sides of the first electrode that is not in contact with the organic layer or on a surface of both sides of the second electrode that is not in contact with the organic layer. The compound according to one embodiment of the present invention applied to the organic layer may be used as a host or dopant of a hole injection layer (120), a hole transport layer (130), a light emitting auxiliary layer (220), an electron transport auxiliary layer, an electron transport layer (150), an electron injection layer (160), a light emitting layer (140), or a material of a light efficiency improvement layer. Preferably, for example, a compound according to Chemical Formula 1 of the present invention may be used as a material of a light emitting auxiliary layer.

[0232] The organic layer may include two or more stacks including a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on the anode, and may further include a charge generation layer formed between the two or more stacks. (See Fig. 3)

[0233] Meanwhile, even if the core is the same, the band gap, electrical properties, and interface properties can vary depending on which substituent is bonded at which position, so the selection of the core and the combination of sub-substituents bonded to it are also very important, and in particular, when the energy level and T1 value between each organic layer, and the inherent properties of the material (mobility, interface properties, etc.) are optimally combined, both a long lifespan and high efficiency can be achieved.

[0234] An organic light emitting device according to one embodiment of the present invention can be manufactured using a PVD (physical vapor deposition) method. For example, a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode, 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 material that can be used as a cathode is deposited thereon.

[0235] In addition, in the present invention, the organic layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, and a roll-to-roll process, and an organic electric device is provided, characterized in that the organic layer includes the compound as an electron transport material.

[0236] As another specific example, the present invention provides an organic electric device characterized in that a compound of the same or different types represented by the chemical formula 1 is mixed and used in the organic layer.

[0237] In addition, the present invention provides a light-emitting auxiliary layer composition comprising a compound represented by the above chemical formula 1, and provides an organic electric device comprising the light-emitting auxiliary layer.

[0238] In addition, the present invention provides an electronic device including a display device including the above-described organic electric element; and a control unit for driving the display device.

[0239] In another aspect, the present invention provides an electronic device characterized in that the organic electroluminescent element is at least one of an organic light-emitting element, an organic solar cell, an organic photoconductor, an organic transistor, and a monochrome or white lighting element. At this time, 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, PDAs, electronic dictionaries, PMPs, remote controls, navigation systems, game consoles, various TVs, and various computers.

[0240]

[0241] Hereinafter, examples of the synthesis of the compound represented by the chemical formula 1 of the present invention and examples of the manufacture of the organic electric device of the present invention will be described in detail, but the present invention is not limited to the following examples.

[0242]

[0243] [Synthesis Example 1]

[0244] The compound (final product) represented by chemical formula 1 according to the present invention can be synthesized as in the following reaction scheme 1, but is not limited thereto.

[0245] <Reaction Scheme 1>

[0246]

[0247] {In the above reaction formula 1, Ar 1 , Ar 2 , Ar a , Ak, R 1 , R 2 , R a , R b , L 1 , L 2 , a and b are the same as defined in the above chemical formula 1, and Hal 1 is Br or Cl.}

[0248]

[0249] I. Synthesis of Sub1

[0250] Sub1 of the above reaction scheme 1 can be synthesized by the reaction path of the following reaction scheme 2, but is not limited thereto.

[0251] <Reaction Formula 2>

[0252]

[0253] 1. Sub1-1 Synthesis Example

[0254]

[0255] 4-bromo-2-chloro-9,9-dimethyl-9H-fluorene (50.0 g, 162.5 mmol) was dissolved in THF (540 mL), and (4-(tert-butyl)phenyl)boronic acid (31.8 g, 178.8 mmol), NaOH (19.5 g, 487.6 mmol), Pd(PPh3)4 (9.39 g, 8.31 mmol), and water (270 mL) were added. The mixture was stirred under reflux 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 resulting compound was then recrystallized through a silica gel column to obtain 52.8 g of the product (yield: 90%).

[0256]

[0257] 2. Sub1-16 Synthesis Example

[0258]

[0259] 4-bromo-2-chloro-9,9-dimethyl-9H-fluorene (50.0 g, 162.5 mmol) was dissolved in THF (540 mL), and (4-(adamantan-1-yl)phenyl)boronic acid (45.8 g, 178.8 mmol), NaOH (19.5 g, 487.6 mmol), Pd(PPh3)4 (9.39 g, 8.31 mmol), and water (270 mL) were added. The mixture was stirred under reflux 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 resulting compound was recrystallized through a silica gel column to obtain 63.5 g of the product (yield: 89%).

[0260]

[0261] 3. Sub1-23 Synthesis Example

[0262]

[0263] 4-bromo-2-chloro-9,9-diphenyl-9H-fluorene (50.0 g, 115.8 mmol) was dissolved in THF (380 mL), and (4-cyclohexylphenyl)boronic acid (26.0 g, 127.4 mmol), NaOH (13.9 g, 347.4 mmol), Pd(PPh3)4 (6.69 g, 5.79 mmol), and water (190 mL) were added. The mixture was stirred under reflux 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 resulting compound was then recrystallized through a silica gel column to obtain 54.4 g of the product (yield: 92%).

[0264]

[0265] Compounds belonging to Sub1 may include, but are not limited to, the compounds below, and Table 1 below shows the FD-MS (Field Desorption-Mass Spectrometry) values ​​of some compounds belonging to Sub1.

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273] 화합물FD-MS화합물FD-MSSub 1-1m / z=360.2(C 25 H 25 Cl=360.9)Sub 1-2m / z=318.1(C 22 H 19 Cl=318.8)Sub 1-3m / z=332.1(C 23 H 21 Cl=332.9)Sub 1-4m / z=346.1(C 24 H 23 Cl=346.9)Sub 1-5m / z=436.2(C 31 H 29 Cl=437)Sub 1-6m / z=368.1(C 26 H 21 Cl=368.9)Sub 1-7m / z=360.2(C 25 H 25 Cl=360.9)Sub 1-8m / z=436.2(C 31 H 29 Cl=437)Sub 1-9m / z=360.2(C 25 H 25 Cl=360.9)Sub 1-10m / z=416.2(C 29 H 33 Cl=417)Sub 1-11m / z=374.2(C 26 H 27 Cl=375)Sub 1-12m / z=416.2(C 29 H 33 Cl=417)Sub 1-13m / z=436.2(C 31 H29 Cl=437)Sub 1-14m / z=386.2(C 27 H 27 Cl=387)Sub 1-15m / z=398.2(C 28 H 27 Cl=399)Sub 1-16m / z=438.2(C 31 H 31 Cl=439)Sub 1-17m / z=462.2(C 33 H 31 Cl=463.1)Sub 1-18m / z=462.2(C 33 H 31 Cl=463.1)Sub 1-19m / z=412.2(C 29 H 29 Cl=413)Sub 1-20m / z=494.3(C 35 H 39 Cl=495.1)Sub 1-21m / z=412.2(C 29 H 29 Cl=413)Sub 1-22m / z=452.2(C 32 H 33 Cl=453.1)Sub 1-23m / z=510.2(C 37 H 31 Cl=511.1)Sub 1-24m / z=520.2(C 38 H 29 Cl=521.1)Sub 1-25m / z=652.3(C 47 H 37 ClO=653.3)Sub 1-26m / z=590.2(C 41 H 31 ClS=591.2)Sub 1-27m / z=366.2(C 25 H 19 D6Cl=367)Sub 1-28m / z=436.2(C 31 H 29 Cl=437)Sub 1-29m / z=448.2(C 32 H 29 Cl=449)Sub 1-30m / z=488.2(C 35 H 33 Cl=489.1)Sub 1-31m / z=385.3(C 25 D 25 Cl=386.1)

[0274] II. Synthesis of Sub2

[0275] Sub2 of the above reaction scheme 1 can be synthesized by the reaction route of the following reaction scheme 3, but is not limited thereto. (Hal 2 is Br or Cl.)

[0276] <Reaction Formula 3>

[0277]

[0278]

[0279] 1. Sub2-3 synthesis example

[0280]

[0281] 2-Bromo-9,9-dimethyl-9H-fluorene (50.0 g, 183.0 mmol) was dissolved in toluene (915 mL) in a round-bottomed flask, and 9,9-dimethyl-9H-fluoren-2-amine (46.0 g, 219.6 mmol), Pd2(dba)3 (5.03 g, 5.49 mmol), P(t-Bu)3 (2.22 g, 10.98 mmol), and NaOt-Bu (35.2 g, 366.0 mmol) were added and stirred at 60°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 resulting compound was purified by silica gel column chromatography and recrystallization to obtain 57.3 g of the product (yield 78%).

[0282]

[0283] 2. Sub2-10 Synthesis Example

[0284]

[0285] 2-Bromo-4'-(tert-butyl)-1,1'-biphenyl (50.0 g, 172.9 mmol) was dissolved in toluene (860 mL) in a round-bottomed flask, 9,9-dimethyl-9H-fluoren-2-amine (43.4 g, 207.5 mmol), Pd2(dba)3 (4.75 g, 5.19 mmol), P(t-Bu)3 (2.10 g, 10.37 mmol), and NaOt-Bu (33.2 g, 345.8 mmol) were added, and the mixture was stirred at 60°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 resulting compound was purified by silica gel column chromatography and recrystallization to obtain 54.1 g of the product (yield 75%).

[0286]

[0287] 3. Sub2-19 Synthesis Example

[0288]

[0289] Sub1-1 (30.0 g, 83.1 mmol) was dissolved in toluene (410 mL) in a round-bottomed flask, 9,9-dimethyl-9H-fluoren-2-amine (20.9 g, 99.8 mmol), Pd2(dba)3 (2.28 g, 2.49 mmol), P(t-Bu)3 (1.01 g, 4.99 mmol), and NaOt-Bu (16.0 g, 166.3 mmol) were added, and the mixture was stirred at 90°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 resulting compound was purified by silica gel column chromatography and recrystallization to obtain 34.2 g of the product (yield 77%).

[0290]

[0291] 4. Sub2-26 Synthesis Example

[0292]

[0293] 2-chloro-9,9-dimethyl-3-phenyl-9H-fluorene (50.0 g, 164.0 mmol) was dissolved in toluene (820 mL) in a round-bottomed flask, dibenzo[b,d]furan-2-amine (36.1 g, 196.9 mmol), Pd2(dba)3 (4.51 g, 4.92 mmol), P(t-Bu)3 (1.99 g, 9.84 mmol), and NaOt-Bu (31.5 g, 328.1 mmol) were added, and the mixture was stirred at 90°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 resulting compound was purified by silica gel column chromatography and recrystallization to obtain 54.1 g of the product (yield 73%).

[0294]

[0295] 5. Sub2-31 Synthesis Example

[0296]

[0297] 3-Bromo-5,5-dimethyl-5H-dibenzo[b,d]silole (50.0 g, 289.2 mmol) was dissolved in toluene (860 mL) in a round-bottomed flask, and 9,9-dimethyl-5-phenyl-9H-fluoren-2-amine (59.2 g, 207.5 mmol), Pd2(dba)3 (4.75 g, 5.19 mmol), P(t-Bu)3 (2.10 g, 10.37 mmol), and NaOt-Bu (33.2 g, 345.8 mmol) were added and stirred at 60°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 resulting compound was purified by silica gel column chromatography and recrystallization to obtain 64 g of the product (yield 75%).

[0298]

[0299] 6. Sub2-45 Synthesis Example

[0300]

[0301] 2'-Bromospiro[fluorene-9,9'-xanthene] (50.0 g, 121.6 mmol) was dissolved in toluene (600 mL) in a round-bottomed flask, dibenzo[b,d]furan-1-amine (26.7 g, 145.9 mmol), Pd2(dba)3 (3.34 g, 3.65 mmol), P(t-Bu)3 (1.48 g, 7.29 mmol), and NaOt-Bu (23.4 g, 243.1 mmol) were added, and the mixture was stirred at 60°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 resulting compound was recrystallized to obtain 53.7 g of the product (yield 86%).

[0302]

[0303] 7. Sub2-50 synthesis example

[0304]

[0305] 2-Bromo-7-(tert-butyl)-9,9-dimethyl-9H-fluorene (50.0 g, 329.3 mmol) was dissolved in toluene (760 mL) in a round-bottomed flask, and 4-(bicyclo[2.2.1]heptan-2-yl)aniline (34.1 g, 182.2 mmol), Pd2(dba)3 (4.17 g, 4.56 mmol), P(t-Bu)3 (1.84 g, 9.11 mmol), and NaOt-Bu (29.2 g, 303.7 mmol) were added and stirred at 60°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 resulting compound was purified by silica gel column chromatography and recrystallization to obtain 47.0 g of the product (yield 71%).

[0306]

[0307] 8. Sub2-63 Synthesis Example

[0308]

[0309] 1-(2'-chloro-[1,1'-biphenyl]-4-yl)adamantane (50.0 g, 154.8 mmol) was dissolved in toluene (770 mL) in a round-bottomed flask, and benzen-d5-amine (18.2 g, 185.8 mmol), Pd2(dba)3 (4.25 g, 4.65 mmol), P(t-Bu)3 (1.88 g, 9.29 mmol), and NaOt-Bu (29.8 g, 309.7 mmol) were added and stirred at 60°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 resulting compound was purified by silica gel column chromatography and recrystallization to obtain 46.5 g of the product (yield 78%).

[0310]

[0311] 9. Sub2-78 Synthesis Example

[0312]

[0313] 3-chloro-3'-cyclohexyl-1,1'-biphenyl (50.0 g, 184.6 mmol) was dissolved in toluene (920 mL) in a round-bottomed flask, and 3-(dibenzo[b,d]thiophen-2-yl)aniline (61.0 g, 221.6 mmol), Pd2(dba)3 (5.07 g, 5.54 mmol), P(t-Bu)3 (2.24 g, 11.08 mmol), and NaOt-Bu (35.5 g, 369.3 mmol) were added and stirred at 60°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 resulting compound was purified by silica gel column chromatography and recrystallization to obtain 68.7 g of the product (yield 73%).

[0314]

[0315] 10. Sub2-92 Synthesis Example

[0316]

[0317] 2-(4-bromophenyl)bicyclo[2.2.1]heptane (50.0 g, 199.0 mmol) was dissolved in toluene (1000 mL) in a round-bottomed flask, and 3-(9-phenyl-9H-fluoren-9-yl)aniline (79.6 g, 238.9 mmol), Pd2(dba)3 (5.47 g, 5.97 mmol), P(t-Bu)3 (2.42 g, 11.94 mmol), and NaOt-Bu (38.3 g, 398.1 mmol) were added and stirred at 60°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 resulting compound was purified by silica gel column chromatography and recrystallization to obtain 79.2 g of the product (yield 79%).

[0318]

[0319] Compounds belonging to Sub2 may include, but are not limited to, the compounds below, and Table 2 below shows the FD-MS (Field Desorption-Mass Spectrometry) values ​​of some compounds belonging to Sub2.

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340] 화합물FD-MS화합물FD-MSUb 2-1m / z=321.2(C 24 H 19 N = 321.4) Sub 2-2m / z = 361.2 (C 27 H 23 N = 361.5) Sub 2-3m / z = 401.2 (C 30 H 27 N = 401.6) Sub 2-4m / z = 401.2 (C 30 H 27 N = 401.6) Sub 2-5m / z = 401.2 (C 30 H 27 N = 401.6) Sub 2-6m / z = 401.2 (C 30 H 27 N = 401.6) Sub 2-7m / z = 477.2 (C 36 H 31 N = 477.7) Sub 2-8m / z = 457.3 (C 34 H 35 N = 457.7) Sub 2-9m / z = 457.3 (C 34 H 35 N = 457.7) Sub 2-10m / z = 417.2 (C 31 H 31 N = 417.6) Sub 2-11m / z = 569.4 (C 42 H 51N=569.9)Sub 2-12m / z=513.3(C 38 H 43 N=513.8)Sub 2-13m / z=489.3(C 36 H 43 N=489.7)Sub 2-14m / z=507.3(C 38 H 37 N=507.7)Sub 2-15m / z=477.2(C 36 H 31 N=477.7)Sub 2-16m / z=609.3(C 46 H 43 N=609.9)Sub 2-17m / z=433.3(C 32 H 35 N=433.6)Sub 2-18m / z=507.3(C 38 H 37 N=507.7)Sub 2-19Mass:533.3C40H39N533.8)Sub 2-20m / z=549.3(C 41 H 43 N=549.8)Sub 2-21m / z=609.3(C 46 H 43 N=609.9)Sub 2-22m / z=493.3(C 37 H 35 N=493.7)Sub 2-23m / z=533.3(C 40 H 39 N=533.8)Sub 2-24m / z=457.3(C 34 H 35 N=457.7)Sub 2-25m / z=375.2(C 27 H 21 NO=375.5)Sub 2-26m / z=451.2(C 33 H 25 NO=451.6)Sub 2-27m / z=425.2(C 31 H 23 NO=425.5)Sub 2-28m / z=375.2(C 27 H 21 NO=375.5)Sub 2-29m / z=349.1(C 24 H 15 NO2=349.4)Sub 2-30m / z=415.1(C 28 H17 NOS=415.5)Sub 2-31m / z=493.2(C 35 H 31 NSi=493.7)Sub 2-32m / z=451.2(C 33 H 25 NO=451.6)Sub 2-33m / z=391.1(C 27 H 21 NS=391.5)Sub 2-34m / z=407.2(C 28 H 25 NS=407.6)Sub 2-35m / z=431.2(C 31 H 29 NO=431.6)Sub 2-36m / z=417.2(C 29 H 27 NSi=417.6)Sub 2-37m / z=606.2(C 42 H 26 N2OS=606.7)Sub 2-38m / z=466.2(C 32 H 26 N2Si=466.7)Sub 2-39m / z=533.3(C 39 H 23 D6NO=533.7)Sub 2-40m / z=571.2(C 40 H 29 NOS=571.7)Sub 2-41m / z=473.3(C 33 H 35 NSi=473.7)Sub 2-42m / z=375.2(C 27 H 21 NO=375.5)Sub 2-43m / z=499.2(C 37 H 25 NO=499.6)Sub 2-44m / z=555.3(C 41 H 33 NO=555.7)Sub 2-45m / z=513.2(C 37 H 23 NO2=513.6)Sub 2-46m / z=567.3(C 42 H 33 NO=567.7)Sub 2-47m / z=456.2(C 33 H 20 D5NO=456.6)Sub 2-48m / z=451.2(C 33H 25 NO=451.6)Sub 2-49m / z=367.2(C 27 H 29 N=367.5)Sub 2-50m / z=435.3(C 32 H 37 N=435.7)Sub 2-51m / z=457.3(C 34 H 35 N=457.7)Sub 2-52m / z=419.3(C 31 H 33 N=419.6)Sub 2-53m / z=251.2(C 18 H 21 N=251.4)Sub 2-54m / z=533.3(C 40 H 39 N=533.8)Sub 2-55m / z=559.3(C 42 H 41 N=559.8)Sub 2-56m / z=397.3(C 29 H 35 N=397.6)Sub 2-57m / z=379.2(C 28 H 29 N=379.5)Sub 2-58m / z=435.3(C 32 H 37 N=435.7)Sub 2-59m / z=571.3(C 43 H 41 N=571.8)Sub 2-60m / z=461.3(C 34 H 39 N=461.7)Sub 2-61m / z=419.3(C 31 H 33 N=419.6)Sub 2-62m / z=495.3(C 37 H 37 N=495.7)Sub 2-63m / z=384.3(C 28 H 24 D5N=384.6)Sub 2-64m / z=513.3(C 38 H 43 N=513.8)Sub 2-65m / z=375.2(C 27 H 21 NO=375.5)Sub 2-66m / z=451.2(C 33 H 25NO=451.6)Sub 2-67m / z=375.2(C 27 H 21 NO=375.5)Sub 2-68m / z=375.2(C 27 H 21 NO=375.5)Sub 2-69m / z=391.1(C 26 H 21 NOSi=391.5)Sub 2-70m / z=379.1(C 25 H 17 NOS=379.5)Sub 2-71m / z=498.3(C 35 H 26 D5NSi=498.8)Sub 2-72m / z=507.3(C 37 H 33 NO=507.7)Sub 2-73m / z=391.1(C 27 H 21 NS=391.5)Sub 2-74m / z=629.3(C 43 H 39 NSSi=629.9)Sub 2-75m / z=431.2(C 31 H 29 NO=431.6)Sub 2-76m / z=599.2(C 42 H 33 NOS=599.8)Sub 2-77m / z=379.1(C 25 H 17 NOS=379.5)Sub 2-78m / z=509.2(C 36 H 31 NS=509.7)Sub 2-79m / z=383.2(C 26 H 29 NSi=383.6)Sub 2-80m / z=409.2(C 29 H 31 NO=409.6)Sub 2-81m / z=471.2(C 33 H 33 NSi=471.7)Sub 2-82m / z=517.2(C 38 H 31 NO=517.7)Sub 2-83m / z=517.2(C 38 H 31 NO=517.7)Sub 2-84m / z=557.3(C 41 H 35NO=557.7)Sub 2-85m / z=585.3(C 43 H 39 NO=585.8)Sub 2-86m / z=469.2(C 34 H 31 NO=469.6)Sub 2-87m / z=469.2(C 34 H 31 NO=469.6)Sub 2-88m / z=251.2(C 18 H 21 N=251.4)Sub 2-89m / z=391.2(C 28 H 25 NO=391.5)Sub 2-90m / z=281.2(C 20 H 27 N=281.4)Sub 2-91m / z=383.2(C 26 H 29 NSi=383.6)Sub 2-92m / z=503.3(C 38 H 33 N=503.7)Sub 2-93m / z=579.3(C 44 H 37 N=579.8)Sub 2-94m / z=501.2(C 38 H 31 N=501.7)Sub 2-95m / z=431.3(C 31 H 21 D 12 N=431.7)Sub 2-96m / z=585.3(C 43 H 39 NO=585.8)Sub 2-97m / z=415.3(C 30 H 41 N=415.7)Sub 2-98m / z=351.2(C 24 HD 16 NO=351.5)

[0341] Ⅲ. Final Product 합성

[0342] 1. P-3 합성예

[0343]

[0344] Sub1-1 (20.0 g, 55.4 mmol) was dissolved in toluene (280 mL) in a round-bottomed flask, and then Sub2-3 (22.3 g, 55.4 mmol), Pd2(dba)3 (1.52 g, 1.66 mmol), P(t-Bu)3 (0.67 g, 3.33 mmol), and NaOt-Bu (16.0 g, 166.3 mmol) were added and stirred under reflux at 125°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 resulting compound was purified by silica gel column chromatography and recrystallization to obtain 35.0 g of the product (yield 87%).

[0345]

[0346] 2. P-10 synthesis example

[0347]

[0348] Sub1-1 (20.0 g, 55.4 mmol) was dissolved in toluene (280 mL) in a round-bottom flask, and then Sub2-10 (23.1 g, 55.4 mmol), Pd2(dba)3 (1.52 g, 1.66 mmol), P(t-Bu)3 (0.67 g, 3.33 mmol), and NaOt-Bu (16.0 g, 166.3 mmol) were added and stirred under reflux at 125°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 resulting compound was purified by silica gel column chromatography and recrystallization to obtain 33.3 g of the product (yield 81%).

[0349]

[0350] 3. P-25 synthetic example

[0351]

[0352] Sub1-1 (20.0 g, 55.4 mmol) was dissolved in toluene (280 mL) in a round-bottomed flask, and then Sub2-25 (20.8 g, 55.4 mmol), Pd2(dba)3 (1.52 g, 1.66 mmol), P(t-Bu)3 (0.67 g, 3.33 mmol), and NaOt-Bu (16.0 g, 166.3 mmol) were added and stirred under reflux at 125°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 resulting compound was purified by silica gel column chromatography and recrystallization to obtain 31.0 g of the product (yield 80%).

[0353]

[0354] 4. P-36 synthetic example

[0355]

[0356] Sub1-11 (20.0 g, 53.3 mmol) was dissolved in toluene (270 mL) in a round-bottom flask, and then Sub2-36 (22.3 g, 53.3 mmol), Pd2(dba)3 (1.47 g, 1.60 mmol), P(t-Bu)3 (0.65 g, 3.20 mmol), and NaOt-Bu (15.4 g, 160.0 mmol) were added and stirred under reflux at 125°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 resulting compound was purified by silica gel column chromatography and recrystallization to obtain 31.5 g of the product (yield 78%).

[0357]

[0358] 5. P-47 synthetic example

[0359]

[0360] Sub1-1 (20.0 g, 55.4 mmol) was dissolved in toluene (280 mL) in a round-bottom flask, and then Sub2-47 (25.3 g, 55.4 mmol), Pd2(dba)3 (1.52 g, 1.66 mmol), P(t-Bu)3 (0.67 g, 3.33 mmol), and NaOt-Bu (16.0 g, 166.3 mmol) were added and stirred under reflux at 125°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 resulting compound was purified by silica gel column chromatography and recrystallization to obtain 33.3 g of the product (yield 77%).

[0361]

[0362] 6. P-70 synthetic example

[0363]

[0364] After dissolving Sub1-15 (20.0 g, 50.1 mmol) in toluene (250 mL) in a round-bottomed flask, Sub2-62 (24.8 g, 50.1 mmol), Pd2(dba)3 (1.38 g, 1.50 mmol), P(t-Bu)3 (0.61 g, 3.01 mmol), and NaOt-Bu (14.5 g, 150.4 mmol) were added and refluxed at 125°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 resulting compound was purified by silica gel column chromatography and recrystallization to obtain 32.7 g of the product (yield 76%).

[0365]

[0366] 7. P-79 synthetic example

[0367]

[0368] Sub1-16 (20.0 g, 45.6 mmol) was dissolved in toluene (250 mL) in a round-bottomed flask, and then Sub2-71 (22.7 g, 45.6 mmol), Pd2(dba)3 (1.25 g, 1.37 mmol), P(t-Bu)3 (0.55 g, 2.73 mmol), and NaOt-Bu (13.1 g, 136.7 mmol) were added and stirred under reflux at 125°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 resulting compound was purified by silica gel column chromatography and recrystallization to obtain 32.0 g of the product (yield 78%).

[0369]

[0370] 8. P-93 synthetic example

[0371]

[0372] Sub1-14 (20.0 g, 51.7 mmol) was dissolved in toluene (260 mL) in a round-bottomed flask, and then Sub2-84 (28.8 g, 51.7 mmol), Pd2(dba)3 (1.42 g, 1.55 mmol), P(t-Bu)3 (0.63 g, 3.10 mmol), and NaOt-Bu (14.9 g, 155.0 mmol) were added and stirred under reflux at 125°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 resulting compound was purified by silica gel column chromatography and recrystallization to obtain 38.0 g of the product (yield 81%).

[0373]

[0374] 9. P-99 synthetic example

[0375]

[0376] Sub1-25 (20.0 g, 30.6 mmol) was dissolved in toluene (150 mL) in a round-bottomed flask, and then Sub2-90 (8.6 g, 30.6 mmol), Pd2(dba)3 (0.84 g, 0.92 mmol), P(t-Bu)3 (0.37 g, 1.84 mmol), and NaOt-Bu (8.8 g, 91.8 mmol) were added and stirred under reflux at 125°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 resulting compound was purified by silica gel column chromatography and recrystallization to obtain 19 g of the product (yield 69%).

[0377]

[0378] 10. P-106 Synthetic Example

[0379]

[0380] Sub1-29 (20.0 g, 44.5 mmol) was dissolved in toluene (220 mL) in a round-bottomed flask, and then Sub2-96 (26.1 g, 44.5 mmol), Pd2(dba)3 (1.22 g, 1.34 mmol), P(t-Bu)3 (0.54 g, 2.67 mmol), and NaOt-Bu (12.8 g, 133.6 mmol) were added and refluxed at 125°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 resulting compound was purified by silica gel column chromatography and recrystallization to obtain 32.0 g of the product (yield 72%).

[0381]

[0382] Meanwhile, the FD-MS values ​​of compounds P-1 to P-136 of the present invention manufactured according to the above-described synthetic examples are as shown in Table 3 below.

[0383] Compound FD-MS Compound FD-MSP-1 m / z = 645.3 (C 49 H 43 N=645.9)P-2m / z=685.4(C 52 H 47N=686.0)P-3m / z=725.4(C 55 H 51 N=726.0)P-4m / z=683.4(C 52 H 45 N=683.9)P-5m / z=697.4(C 53 H 47 N=698.0)P-6m / z=711.4(C 54 H 49 N=712.0)P-7m / z=801.4(C 61 H 55 N=802.1)P-8m / z=781.5(C 59 H 59 N=782.1)P-9m / z=781.5(C 59 H 59 N=782.1)P-10m / z=741.4(C 56 H 55 N=742.1)P-11m / z=893.6(C 67 H 75 N=894.3)P-12m / z=837.5(C 63 H 67 N=838.2)P-13m / z=889.6(C 67 H 71 N=890.3)P-14m / z=839.4(C 64 H 57 N=840.2)P-15m / z=801.4(C 61 H 55 N=802.1)P-16m / z=1009.6(C 77 H 71 N=1010.4)P-17m / z=757.5(C 57 H 59 N=758.1)P-18m / z=831.5(C 63 H 61 N=832.2)P-19m / z=857.5(C 65 H 63 N=858.2)P-20m / z=873.5(C 66 H 67 N=874.3)P-21m / z=933.5(C 71 H 67 N=934.3)P-22m / z=817.5(C 62 H 59N=818.2)P-23m / z=857.5(C 65 H 63 N=858.2)P-24m / z=781.5(C 59 H 59 N=782.1)P-25m / z=699.4(C 52 H 45 NO=699.9)P-26m / z=775.4(C 58 H 49 NO=776.0)P-27m / z=749.4(C 56 H 47 NO=750.0)P-28m / z=699.4(C 52 H 45 NO=699.9)P-29m / z=673.3(C 49 H 39 NO2=673.9)P-30m / z=795.4(C 57 H 49 NOS=796.1)P-31m / z=817.4(C 60 H 55 NSi=818.2)P-32m / z=775.4(C 58 H 49 NO=776.0)P-33m / z=715.3(C 52 H 45 NS=716.0)P-34m / z=731.4(C 53 H 49 NS=732.0)P-35m / z=755.4(C 56 H 53 NO=756.0)P-36m / z=755.4(C 55 H 53 NSi=756.1)P-37m / z=930.4(C 67 H 50 N2OS=931.2)P-38m / z=790.4(C 57 H 50 N2Si=791.1)P-39m / z=857.5(C 64 H 47 D6NO=858.2)P-40m / z=895.4(C 65 H 53 NOS=896.2)P-41m / z=797.4(C 58 H 59NSi=798.2)P-42m / z=755.4(C 56 H 53 NO=756.0)P-43m / z=823.4(C 62 H 49 NO=824.1)P-44m / z=879.4(C 66 H 57 NO=880.2)P-45m / z=837.4(C 62 H 47 NO2=838.1)P-46m / z=891.4(C 67 H 57 NO=892.2)P-47m / z=780.4(C 58 H 44 D5NO=781.1)P-48m / z=851.4(C 64 H 53 NO=852.1)P-49m / z=671.4(C 51 H 45 N=671.9)P-50m / z=723.4(C 55 H 49 N=724.0)P-51m / z=803.4(C 61 H 57 N=804.1)P-52m / z=691.4(C 52 H 53 N=692.0)P-53m / z=827.4(C 63 H 57 N=828.2)P-54m / z=763.4(C 58 H 53 N=764.1)P-55m / z=879.5(C 67 H 61 N=880.2)P-56m / z=759.5(C 57 H 61 N=760.1)P-57m / z=807.5(C 61 H 61 N=808.2)P-58m / z=779.4(C 59 H 57 N=780.1)P-59m / z=803.4(C 61 H 57 N=804.1)P-60m / z=743.4(C 56 H 57 N=744.1)P-61m / z=677.4(C 51 H51 N=678.0)P-62m / z=909.5(C 69 H 67 N=910.3)P-63m / z=1017.6(C 77 H 79 N=1018.5)P-64m / z=721.5(C 54 H 59 N=722.1)P-65m / z=729.4(C 55 H 55 N=730.1)P-66m / z=797.5(C 60 H 63 N=798.2)P-67m / z=973.6(C 74 H 71 N=974.4)P-68m / z=785.5(C 59 H 63 N=786.2)P-69m / z=769.5(C 58 H 59 N=770.1)P-70m / z=857.5(C 65 H 63 N=858.2)P-71m / z=786.5(C 59 H 54 D5N=787.2)P-72m / z=837.5(C 63 H 67 N=838.2)P-73m / z=725.4(C 54 H 47 NO=726.0)P-74m / z=813.4(C 61 H 51 NO=814.1)P-75m / z=777.4(C 58 H 51 NO=778.1)P-76m / z=699.4(C 52 H 45 NO=699.9)P-77m / z=741.3(C 53 H 47 NOSi=742.0)P-78m / z=755.3(C 54 H 45 NOS=756.0)P-79m / z=900.5(C 66 H 56 D5NSi=901.3)P-80m / z=831.4(C 62 H 57NO=832.1)P-81m / z=741.3(C 54 H 47 NS=742.0)P-82m / z=991.5(C 71 H 65 NSSi=992.5)P-83m / z=833.5(C 62 H 59 NO=834.2)P-84m / z=741.4(C 54 H 51 NSi=742.1)P-85m / z=949.4(C 69 H 59 NOS=950.3)P-86m / z=741.3(C 53 H 43 NOS=742.0)P-87m / z=911.5(C 67 H 61 NS=912.3)P-88m / z=707.4(C 51 H 53 NSi=708.1)P-89m / z=759.4(C 56 H 57 NO=760.1)P-90m / z=833.4(C 61 H 59 NSi=834.2)P-91m / z=933.5(C 70 H 63 NO=934.3)P-92m / z=841.4(C 63 H 55 NO=842.1)P-93m / z=907.5(C 68 H 61 NO=908.2)P-94m / z=947.5(C 71 H 65 NO=948.3)P-95m / z=871.5(C 65 H 61 NO=872.2)P-96m / z=793.4(C 59 H 55 NO=794.1)P-97m / z=725.4(C 55 H 51 N=726.0)P-98m / z=875.4(C 66 H 53 NO=876.2)P-99m / z=897.5(C 67 H 63 NO=898.2)P-100m / z=937.4(C67 H 59 NSSi=938.4)P-101m / z=853.5(C 65 H 59 N=854.2)P-102m / z=941.5(C 72 H 63 N=942.3)P-103m / z=903.5(C 69 H 61 N=904.3)P-104m / z=761.6(C 56 H 39 D 18 N=762.2)P-105m / z=957.5(C 72 H 63 NO=958.3)P-106m / z=997.5(C 75 H 67 NO=998.4)P-107m / z=867.6(C 65 H 73 N=868.3)P-108m / z=700.6(C 49 D 41 NO=701.1)P-109m / z=657.3(C 49 H 39 NO=657.8)P-110m / z=699.3(C 52 H 45 NO=699.9)P-111m / z=725.3(C 54 H 47 NO=725.9)P-112m / z=737.3(C 55 H 47 NO=737.9)P-113m / z=733.3(C 55 H 43 NO=733.9)P-114m / z=755.4(C 56 H 53 NO=756.0)P-115m / z=777.4(C 58 H 51 NO=778.0)P-116m / z=813.4(C 61 H 51 NO=814.0)P-117m / z=851.3(C 63 H 49 NS=852.1)P-118m / z=993.4(C 74 H 59 NS=994.3)P-119m / z=1200.54(C92 H 68 N2=1201.5)P-120m / z=1166.5(C 89 H 70 N2=1167.5)P-121m / z=877.3(C 68 H 47 N=878.1)P-122m / z=803.4(C 61 H 57 N=804.1)P-123m / z=645.3(C 49 H 43 N=645.8)P-124m / z=735.3(C 55 H 45 NO=735.9)P-125m / z=609.3(C 46 H 43 N=609.8)P-126m / z=747.4(C 56 H 49 D6N=748.1)P-127m / z=714.4(C 53 H 38 D 13 N=715.0)P-128m / z=632.4(C 47 H 36 D9N=632.9)P-129m / z=647.3(C 49 H 37 D4N=647.9)P-130m / z=719.4(C 53 H 41 D6NO=720.0)P-131m / z=744.3(C 54 H 44 D5NSi=745.1)P-132m / z=835.4(C 61 H 57 NS=836.1)P-133m / z=931.4(C 72 H 53 N=932.2)P-134m / z=726.3(C 54 H 35 D5NO=726.9)P-135m / z=706.4(C 53 H 46 D5N=707.03)P-136m / z=711.3(C 54 H 49 N=711.9)

[0384] Meanwhile, although the exemplary synthetic examples of the present invention represented by Chemical Formula 1 have been described above, 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 it will be easily understood by those skilled in the art that the above reaction proceeds even if a substituent other than the substituent specified in the specific synthetic examples is combined.

[0385]

[0386] Manufacturing and evaluation of organic electronic devices

[0387] [Example 1] Red organic light-emitting device (luminescent auxiliary layer)

[0388] First, N is formed on the ITO layer (anode) formed on the glass substrate. 1 -(naphthalen-2-yl)-N 4 ,N 4 -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N 1 -Phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) was vacuum-deposited to a thickness of 60 nm to form a hole injection layer, and then N,N'-bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviated as NPB) was vacuum-deposited to a thickness of 60 nm on the hole injection layer to form a hole transport layer.

[0389] Next, the compound P-3 of the present invention was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light-emitting auxiliary layer. Next, on the light-emitting auxiliary layer, 4,4'-N,N'-dicarbazole-biphenyl (hereinafter abbreviated as CBP) was used as a host material, and bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate (hereinafter abbreviated as (piq)2Ir(acac)) was used as a dopant, and the dopant was doped such that the weight ratio of the host and the dopant was 95:5, thereby forming a light-emitting layer having a thickness of 30 nm.

[0390] Next, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited on the light-emitting layer to form a hole-blocking layer with a thickness of 10 nm, and Tris(8-hydroxyquinolinato)aluminum (hereinafter abbreviated as Alq3) was vacuum-deposited on the hole-blocking layer to a thickness of 40 nm to form an electron-transporting layer. Thereafter, 8-quinolinolato lithium (hereinafter abbreviated as Liq) was deposited on the electron-transporting layer to form an electron-injection layer with a thickness of 0.2 nm, and then Al was deposited to form a cathode with a thickness of 150 nm.

[0391]

[0392] [Example 2] to [Example 20]

[0393] 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-3 of the present invention as a light-emitting auxiliary layer material.

[0394]

[0395] [Comparative Example 1] to [Comparative Example 5]

[0396] An organic light-emitting device was manufactured in the same manner as in Example 1, except that Comparative Compounds A to E were used instead of Compound P-3 of the present invention as a light-emitting auxiliary layer material.

[0397] Comparative Compound A Comparative Compound B Comparative Compound C

[0398]

[0399] Comparative Compound D Comparative Compound E

[0400]

[0401] The electroluminescence (EL) characteristics were measured using PR-650 from Photoresearch by applying a forward bias DC voltage to the organic electroluminescence devices manufactured by Examples 1 to 20 and Comparative Examples 1 to 5 of the present invention, and the measurement result was 2,500 cd / m 2 The T95 lifespan was measured using a lifespan measuring device manufactured by Maxscience at a reference luminance. Table 4 below shows the results of the device fabrication and evaluation.

[0402] This measuring device allows the performance of new materials to be evaluated against reference compounds under identical conditions, without being affected by possible daily variations in deposition rate, vacuum quality or other parameters.

[0403] Since, during the evaluation, one batch contains four identically prepared OLEDs including a comparative compound, and the performance of a total of 12 OLEDs is evaluated in three batches, the values ​​of the experimental results obtained in this way exhibit statistical significance.

[0404] Compound driving voltage (V) current (mA / cm) 2 ) Luminance (cd / m 2) Efficiency (cd / A) T (95) Comparative Example (1) Comparative Compound A 5.5 15.6 2500.016.08 1.8 Comparative Example (2) Comparative Compound B 5.6 15.9 2500.015.78 2.6 Comparative Example (3) Comparative Compound C 5.2 13.7 2500.018.29 2.4 Comparative Example (4) Comparative Compound D 5.3 14.3 2500.017.59 1.3 Comparative Example (5) Comparative Compound E5.413.32500.018.890.9Embodiment (1)P-34.910.42500.024.0116.5Embodiment (2)P-104.810.02500.025.0119.6Embodiment (3)P-255.011.32500.022.1107.8Embodiment (4)P-315.011.02500.022.7110.8Embodiment (5)P-475.011.32500 .022.2107.4Embodiment (6)P-504.910.52500.023.9115.8Embodiment (7)P-905.011.02500.022.8109.2Embodiment (8)P-915.011.12500.022.5107.7Embodiment (9)P-985.111.72500.021.4105.5Embodiment (10)P-1085.011.22500.022.4112 .0Embodiment (11)P-1215.111.52500.021.7106.4Embodiment (12)P-1225.111.82500.021.1106.1Embodiment (13)P-1234.910.62500.023.6113.5Embodiment (14)P-1245.010.92500.022.9108.1Embodiment (15)P-1254.910.62500.023.6117. 5Example (16) P-1264.810.12500.024.8120.1Example (17) P-1274.810.32500.024.2114.3Example (18) P-1334.910.32500.024.2116.6Example (19) P-1354.910.72500.023.3113.2Example (20) P-1364.810.52500.023.9117.6

[0405] As can be seen from the results in Table 4 above, when a red organic light-emitting device is manufactured using a material for an organic light-emitting device, it can be confirmed that the driving voltage, efficiency, and lifespan of the organic light-emitting device are significantly improved in the examples using the compound of the present invention compared to the comparative examples using comparative compounds A to E as a light-emitting auxiliary layer.

[0406] Comparative compounds A to E are similar to the compounds of the present invention in that they are tertiary amine compounds containing a fluorene skeleton substituted in the molecule, but in the case of Comparative compounds A and B, R of the chemical formula 1 of the present invention a and R b Comparative Compounds C and D are similar in that a substituent is introduced at position 4 of fluorene, but are different from the compound of the present invention in that the substituent does not include an alkyl group or an aliphatic ring group. Comparative Compound E is similar in that a substituent including an alkyl group or an aliphatic ring group is substituted on a fluorene moiety, but the substitution position is different from the compound of the present invention.

[0407] To examine the influence of the compositional differences of these compounds, data measured using the DFT method (B3LYP / 6-31g(D)) of the Gaussian program for the comparative compounds and the compound of the present invention are as shown in Table 5.

[0408] Compound HOMO (eV) Comparative Compound A4.868 Comparative Compound B4.793 Comparative Compound C4.834 Comparative Compound D4.815 Comparative Compound E4.725 P-34.647

[0409] As can be seen from the results in Table 5 above, it can be confirmed that the HOMO Energy Level (hereinafter, HOMO) value of the present invention is shallower than the HOMO values ​​of Comparative Compounds A to E. As a result, when the compound of the present invention is applied to a device, it is thought that the driving voltage of the device is significantly reduced as hole injection and hole transfer from the hole transport layer to the light-emitting auxiliary layer become easier than in other comparative compounds.

[0410] For further verification, the Reorganization Energy (unit: eV, hereinafter RE) of the compounds of the present invention and comparative compounds hole ), Hole Small Polaron Stabilization Energy (unit: eV, HSPSE) and Hole Neutral Stabilization Energy (unit: eV, HNSE) were measured using molecular simulation (Schrodinger Materials Science Suite 4.9.128) and the data are shown in Table 6.

[0411] Compound RE hole (eV)HSPSE(eV)HNSE(eV)Comparative Compound A0.21270.10930.1034Comparative Compound B0.14540.07090.0744Comparative Compound C0.14970.07320.0765Comparative Compound D0.12430.06540.0588Comparative Compound E0.17560.09410.0815P-30.11400.05910.0549

[0412] As can be seen from the results in Table 6 above, compound P-3 of the present invention has a higher RE than comparative compounds A to E. hole , it can be seen that the HSPSE and HNSE values ​​are significantly lower.

[0413] First RE hole When compared, RE of the compound of the present invention holeIt can be confirmed that the value is significantly lower than that of other comparative compounds. As a result, when the compound of the present invention is applied to a device, hole hopping occurs more quickly within the material than in the comparative compounds, thereby improving hole mobility and allowing faster hole transfer to the light-emitting layer, which improves charge balance and significantly improves the operation and efficiency of the device.

[0414] Next, when comparing the HSPSE and HNSE values, it can be confirmed that the HSPSE and HNSE values ​​of the compound of the present invention are significantly lower than those of the comparative compounds. This means that the compound of the present invention can reach a stable state more quickly and with less energy than the comparative compounds after receiving holes in the hole transport layer or transferring holes to the light-emitting layer within the device, and as a result, it is thought that the lifespan of the device is significantly improved.

[0415] In other words, as can be seen from the results in Tables 4 to 6, it can be confirmed that the compound satisfying all the structural features and configurations disclosed in the present invention exhibits a remarkable effect in the organic electric device, compared to the comparative compounds A to E having a structurally similar configuration to the compound of the present invention. This shows that the compound of the present invention satisfying all the specific configurations exhibits a remarkable effect, compared to other comparative compounds not described in the present specification.

[0416] These results suggest that even if the molecular components are similar, the properties of the compound, such as hole characteristics, light efficiency characteristics, energy levels, hole injection and mobility characteristics, charge balance of holes and electrons, volume density, and intermolecular distance, can differ significantly to an extent that is difficult to predict depending on the type and position of the substituted substituent, and that the performance of the device can vary not only due to the composition of a single compound but also due to complex factors.

[0417] In the case of a light-emitting auxiliary layer, it is necessary to understand the relationship between the hole transport layer and the light-emitting layer (host). Therefore, even if a similar core is used, it would be very difficult for even a person skilled in the art to infer the characteristics exhibited by the light-emitting auxiliary layer in which the compound of the present invention is used.

[0418] In addition, the evaluation results of the above-described device fabrication described the device characteristics in which the compound of the present invention was applied only to the light-emitting auxiliary layer, but the compound of the present invention can be applied to the hole transport layer or applied to both the hole transport layer and the light-emitting auxiliary layer.

[0419] The above description is merely illustrative of the present invention, and those skilled in the art will appreciate that various modifications may be made without departing from the essential characteristics of the present invention. Therefore, the embodiments disclosed in this specification are intended to illustrate, not limit, the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The scope of protection of the present invention should be interpreted by the following claims, and all techniques within a scope equivalent thereto should be interpreted as being included within the scope of the present invention.

[0420] According to the present invention, an organic device having excellent device characteristics such as high brightness, high luminescence, and long lifespan can be manufactured, and thus has industrial applicability.

Claims

1. A compound represented by the following chemical formula 1 Chemical Formula 1 {In the above chemical formula 1, L 1 and L 2 are independently of each other and are single bonds; C6~C 60 C2~C containing an arylene group; a fluorenylene group; and at least one heteroatom selected from O, N, S, Si, and P 60 is selected from the group consisting of heterocyclic groups; Ar 1 and Ar 2 are independently C6~C 60 C2~C containing an aryl group; a fluorenyl group; and at least one heteroatom selected from O, N, S, Si, and P 60 is selected from the group consisting of heterocyclic groups; R a and R b 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; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 is selected from the group consisting of aryloxy group of R; or a and R b can combine with each other to form a spirobifluorene group, R 1 and R 2 are identical or different from each other, and independently of each other, hydrogen; deuterium; 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 and C6~C 60 Fused ring group of aromatic ring; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 An aryloxy group of R is selected from the group consisting of, or a plurality of adjacent R 1 R's or multiple R's 2 They can combine with each other to form rings, a is an integer from 0 to 4, b is an integer from 0 to 2, Ar a is C6~C 60 arylene group; and Ak is C1~C 50 alkyl group of; or C3~C 60 is an aliphatic ring; Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 Alkylthio group of; C1~C 20 Alkoxyl group of; C6~C 20 Aryloxy group of; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkyne group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 Aryl group of; Fluorenyl group; C2~C 20 Heterocyclic group of; C3~C 20 Aliphatic ring group; C7~C 20 Arylalkyl group of; C8~C 20 Aryl alkenyl group of; and C7~C 20 It may be further substituted with one or more substituents selected from the group consisting of alkylaryl groups; and further, the hydrogen of these substituents may be further substituted with one or more deuteriums, and further, these substituents may be combined with each other to form a ring, wherein the 'ring' means C3~C 60 Aliphatic ring or C6~C 60 Aromatic ring or C2~C 60 A fused ring composed of a heterocycle or a combination thereof, including a saturated or unsaturated ring.

2. In the first paragraph, the Ar 1 or Ar 2 One of which is at least one C1~C 20 alkyl group of; or C3~C 20 A compound characterized by being substituted with an aliphatic ring group; 3. In the first paragraph, the chemical formula 1 is a compound characterized by being represented by the following chemical formula 1-1. Chemical Formula 1-1 {In the above chemical formula 1-1, R a , R b , R 1 , R 2 , a, b, Ar a , Ak, L 1 , L 2 and Ar 2 is the same as defined in claim 1 above, Ar 3 Silver C6~C 60 Arylene group of; or C2~C containing at least one heteroatom among O, N, S, Si and P 60 is a heterocyclic group; and Ak 2 is C1~C 20 alkyl group of; or C3~C 20 is a fatty acid ring; 4. In the first paragraph, the compound is characterized in that the Ak is represented by any one of the following chemical formulas Ak-1 to Ak-8. Chemical formula Ak-1 Chemical formula Ak-2 Chemical formula Ak-3 Chemical formula Ak-4 Chemical formula Ak-5 Chemical formula Ak-6 Chemical formula Ak-7 Chemical formula Ak-8 {In the above chemical formulas Ak-1 to Ak-8, * indicates the position where it is combined, The above chemical formulas Ak-1 to Ak-8 may be further substituted with one or more deuterium atoms.

5. In the first paragraph, the Ar 1 or Ar 2 A compound characterized in that any one of them is represented by any one of the following chemical formulas Ar-1 to Ar-11 Chemical formula Ar-1 Chemical formula Ar-2 Chemical formula Ar-3 Chemical formula Ar-4 Chemical formula Ar-5 Chemical formula Ar-6 Chemical formula Ar-7 Chemical formula Ar-8 Chemical formula Ar-9 Chemical formula Ar-10 Chemical formula Ar-11 {In the above chemical formulas Ar-1 to Ar-11, R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 are identical or different from each other, and independently of each other, hydrogen; deuterium; C6~C 20 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 20 Heterocyclic group of; C3~C 20 Aliphatic ring group; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 20 Alkoxyl group of; and C6~C 20 is selected from the group consisting of aryloxy groups; or a plurality of adjacent groups can be combined with each other to form a ring, R c is C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C6~C 60 C2~C containing an aryl group of; and at least one heteroatom of O, N, S, Si and P 60 is selected from the group consisting of heterocyclic groups; R d is hydrogen; deuterium; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C6~C 60 C2~C containing an aryl group of; and at least one heteroatom of O, N, S, Si and P 60 is selected from the group consisting of heterocyclic groups; R c and R d can combine with each other to form spiro rings, g is an integer from 0 to 5, h, k, l, o, p and q are each independently an integer from 0 to 4, i is an integer from 0 to 7, j is an integer from 0 to 9, m and n are each independently an integer from 0 to 3, W is O, S, CR 27 R 28 , SiR 27 R 28 or NR 29 And, R 27 , R 28 and R 29 are independently C6~C 20 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 20 Heterocyclic group of; C3~C 20 Aliphatic ring and C6~C 20 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 Alkoxyl group of; and C6~C 20 is selected from the group consisting of aryloxy group of R; or 27 and R 28 These can be combined to form rings, * indicates the position where it is combined.} 6. In the first paragraph, the Ar a , L 1 and L 2 A compound characterized by being selected from a single bond or one of the following chemical formulas L-1 to L-27. [Chemical Formula L-1] [Chemical Formula L-2] [Chemical Formula L-3] [Chemical Formula L-4] [Chemical Formula L-5] [Chemical Formula L-6] [Chemical Formula L-7] [Chemical Formula L-8] [Chemical Formula L-9] [Chemical Formula L-10] [Chemical Formula L-11] [Chemical Formula L-12] [Chemical Formula L-13] [Chemical Formula L-14] [Chemical Formula L-15] [Chemical Formula L-16] [Chemical Formula L-17] [Chemical Formula L-18] [Chemical Formula L-19] [Chemical Formula L-20] [Chemical Formula L-21] [Chemical Formula L-22] [Chemical Formula L-23] [Chemical Formula L-24] [Chemical Formula L-25] [Chemical Formula L-26] [Chemical Formula L-27] {In the above chemical formulas L-1 to L-27, Z is O, S, CR 30 R 31 or N-Ar 5 and, R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 and R 27 R of the above claim 5 7 Same as the definition of , or adjacent multiple groups can be combined to form a ring, Ar 5 is C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C6~C 20 C2~C containing an aryl group of; and at least one heteroatom of O, N, S, Si and P 20 is selected from the group consisting of heterocyclic groups; r, t, v, w, x and y are independently integers from 0 to 4, s is an integer from 0 to 6, u is an integer from 0 to 2, z is an integer from 0 to 3, aa is an integer from 0 to 5, * indicates the position where it is combined.} 7. In the first paragraph, the L 1 , L 2 , Ar 1 and Ar 2 A compound characterized in that at least one of the substituents contains deuterium.

8. A compound according to claim 1, characterized in that the compound represented by the chemical formula 1 is any one of the following compounds P-1 to P-136.

9. An organic electric device comprising an anode, a cathode, and an organic layer formed between the anode and the cathode, wherein the organic layer comprises a single compound represented by the chemical formula 1 of claim 1 or two or more compounds.

10. An organic electric device according to claim 9, wherein the organic layer comprises at least one of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer.

11. An organic electric device according to claim 9, wherein the organic layer is a light-emitting auxiliary layer.

12. An organic electric device according to claim 9, further comprising a light efficiency improvement layer formed on at least one surface of the anode and cathode opposite to the organic layer.

13. An organic electric device according to claim 9, 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 an anode.

14. An organic electric device according to claim 13, characterized in that the organic layer further includes a charge generation layer formed between the two or more stacks.

15. An electronic device comprising a display device including an organic electric element of clause 9; and a control unit for driving the display device.

16. An electronic device according to claim 15, wherein the organic electroluminescent element is at least one of an organic light-emitting diode (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a monochrome or white lighting element.

17. A step of depositing an organic light-emitting material including a compound represented by the chemical formula 1 of claim 1 in a manufacturing process of an organic light-emitting device; A step of removing impurities from an unrefined organic light-emitting material recovered from a deposition device; A step of recovering the removed impurities; and A method for reusing a compound represented by chemical formula 1 according to claim 1, comprising a step of purifying the recovered impurities to a purity of 99.9% or higher.

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