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

[0003] Materials used as organic layers in organic electronic devices can be classified into light-emitting materials and charge-transporting materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their functions. In addition, the light-emitting materials can be classified into high-molecular and low-molecular types depending on their molecular weight, and can be classified into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons depending on their luminescence mechanism. In addition, light-emitting materials can be classified into blue, green, and red light-emitting materials depending on their luminescence color, and yellow and orange light-emitting materials required to realize better natural colors.

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

[0005] The current portable display market is trending toward larger displays, which are increasing in size and demanding greater power consumption than traditional portable displays. Therefore, power consumption has become a crucial factor for portable displays, which rely on batteries as their limited power source. Efficiency and longevity also need to be addressed.

[0006] Efficiency, lifespan, and operating voltage are all interrelated. As efficiency increases, the operating voltage relatively decreases. As the operating voltage decreases, the crystallization of organic materials due to Joule heating generated during operation decreases, which tends to result in a longer lifespan. However, efficiency cannot be maximized simply by improving the organic layer. This is because long lifespan and high efficiency can be achieved simultaneously when the energy level and T1 value between each organic layer, and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined.

[0007] Therefore, it is necessary to delay the penetration and diffusion of metal oxide from the anode electrode (ITO), which is one of the causes of shortened lifespan of organic electronic devices, into the organic layer, and to have stable characteristics against Joule heating generated when the device is operated. In addition, OLED devices are mainly formed by a deposition method, so there is a need to develop materials that can withstand the deposition process for a long time, i.e., materials with strong heat resistance.

[0008] In other words, in order to fully demonstrate the excellent characteristics of organic electronic devices, the materials that make up the organic layers within the devices, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection 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 among them, the development of host materials for the light-emitting layer is particularly urgent.

[0009] 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.

[0010] Accordingly, the present invention aims to provide a novel compound, an organic electric element using the same, and an electronic device thereof.

[0011] The present invention provides a compound represented by the following chemical formula 1.

[0012] <Chemical Formula 1>

[0013]

[0014] In another aspect, the present invention provides a composition for a phosphorescent light-emitting layer of an organic electric device comprising a mixture of a compound represented by the above chemical formula 1 and a compound represented by the following chemical formula 2.

[0015] <Chemical Formula 2>

[0016]

[0017] In another aspect, the present invention provides an organic electric device and an electronic device thereof comprising a compound represented by the above chemical formula 1 or a material for an organic electric device.

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

[0019] Figures 1 to 3 are exemplary diagrams of an organic light-emitting device according to the present invention.

[0020] Figure 4 shows a chemical formula according to one aspect of the present invention.

[0021] 100, 200, 300: Organic electric element 110: First electrode

[0022] 120: hole injection layer 130: hole transport layer

[0023] 140: Emitting layer 150: Electron transport layer

[0024] 160: Electron injection layer 170: Second electrode

[0025] 180: Light efficiency improvement layer 210: Buffer layer

[0026] 220: Light-emitting auxiliary layer 320: First hole injection layer

[0027] 330: First hole transport layer 340: First light-emitting layer

[0028] 350: First electron transport layer 360: First charge generation layer

[0029] 361: Second charge generation layer 420: Second hole injection layer

[0030] 430: Second hole transport layer 440: Second light-emitting layer

[0031] 450: Second electron transport layer CGL: Charge generation layer

[0032] ST1: First stack ST2: Second stack

[0033] 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.

[0034] 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.

[0035] As used in this specification and the appended claims, unless otherwise stated, the following terms have the following meanings:

[0036] The term “halo” or “halogen” as used herein, unless otherwise stated, means fluorine (F), bromine (Br), chlorine (Cl), or iodine (I).

[0037] 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.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] The term “heteroatom” as used herein refers to N, O, S, P or Si unless otherwise stated.

[0047] 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.

[0048]

[0049] 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.

[0050] 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.

[0051]

[0052] 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.

[0053] 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.

[0054] 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.

[0055] Other heterocyclic compounds or heteroradicals other than the aforementioned heterocyclic compounds include, but are not limited to, one or more heteroatoms.

[0056] 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~C20 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 deuterium 20 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.

[0057] 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.

[0058] 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.

[0059]

[0060] 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 1 is 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.

[0061]

[0062] 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.

[0063] [Example of ortho-position]

[0064]

[0065] [Example of meta-position]

[0066]

[0067] [Example of para-location]

[0068]

[0069]

[0070] The term "composition" as used herein is intended to be broadly interpreted to include not only compounds but also solutions, dispersions, liquids, and solid mixtures (mixtures, admixtures). The composition of the present invention may contain the compound of the present invention alone, or may contain two or more different compounds in combination, or may contain the compound in combination with two or more other compounds. In other words, the composition may contain the compound corresponding to Chemical Formula 1 alone, may contain a mixture of two or more compounds of Chemical Formula 1, or may contain a mixture of the compound of Chemical Formula 1 and a compound not corresponding to the present invention. Here, the compound not corresponding to the present invention may be a single compound, or may be two or more compounds. In this case, when the compound is contained in a combination of two or more other compounds, the other compounds may be already known compounds of each organic layer, or may be compounds to be developed in the future. In this case, the compounds contained in the organic layer may be composed solely of compounds of the same type, but may also be a mixture of two or more heterogeneous compounds represented by Chemical Formula 1.

[0071]

[0072] Hereinafter, a compound according to one aspect of the present invention, a composition for a phosphorescent light-emitting layer of an organic electric device, and an organic electric device including the same will be described.

[0073] The present invention provides a compound represented by the following chemical formula 1.

[0074] <Chemical Formula 1>

[0075]

[0076] In the above chemical formula 1, each symbol can be defined as follows.

[0077] A ring is C 10 is an aryl group,

[0078] R 1 , R 2 and R 3 are independently of each other, the same or different, 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; 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 groups; or adjacent multiple R 2 R's or multiple R's 3 They can combine with each other to form rings,

[0079] The above R 1 , R 2 and R 3 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.

[0080] The above R 1 , R 2 and R 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.

[0081] The above R 1 , R 2 and R 3 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.

[0082] The above R 1 , R 2 and R 3 If it is an alkoxyl group, preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkoxyl group.

[0083] The above R 1 , R 2 and R 3 If it is an aryloxy group, preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an aryloxy group.

[0084] Ar 1 and Ar 2 are independently C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; and C3~C 60 Aliphatic ring and C6~C60 A fused ring group of an aromatic ring is selected from the group consisting of;

[0085] 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.

[0086] 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.

[0087] The above Ar 1 and Ar 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.

[0088] a is an integer from 0 to 11, b is an integer from 0 to 4, c is an integer from 0 to 3,

[0089] Here, the aryl group and heterocyclic group are deuterium, C1~C20 Alkyl group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 Aryl group of; C2~C 20 may be further substituted with one or more substituents selected from the group consisting of heterocyclic groups.

[0090] In addition, the present invention provides a compound in which the chemical formula 1 is represented by any one of the following chemical formulas 3 to 10.

[0091] <Chemical Formula 3> <Chemical Formula 4>

[0092]

[0093] <Chemical Formula 5> <Chemical Formula 6>

[0094]

[0095] <Chemical Formula 7> <Chemical Formula 8>

[0096]

[0097] <Chemical Formula 9> <Chemical Formula 10>

[0098]

[0099] {In the above chemical formulas 3 to 10,

[0100] R 1 , R 2 , R 3 , Ar 1 , Ar 2 , b and c are as defined above,

[0101] a' is an integer from 0 to 11.

[0102] In addition, the present invention comprises the Ar 1 and Ar 2 Provided is a compound represented by any one of the following chemical formulas a-1 to a-15.

[0103] <Chemical Formula A-1> <Chemical Formula A-2> <Chemical Formula A-3> <Chemical Formula A-4>

[0104]

[0105] <Chemical Formula A-5> <Chemical Formula A-6> <Chemical Formula A-7> <Chemical Formula A-8>

[0106]

[0107] <Chemical Formula A-9> <Chemical Formula A-10> <Chemical Formula A-11>

[0108]

[0109] <Chemical Formula a1-12> <Chemical Formula a-13> <Chemical Formula a-14> <Chemical Formula a-15>

[0110]

[0111] In the above chemical formulas a-1 to a-15, each symbol can be defined as follows.

[0112] R 4 are each identical or different and independently of each other deuterium; C6~C 20 Aryl group of; and C6~C substituted with deuterium 20 aryl group of; selected from the group consisting of, or adjacent multiple R 4 They can combine with each other to form rings,

[0113] d and f are independently integers from 0 to 5, e is an integer from 0 to 4, g and i are independently integers from 0 to 7, h is an integer from 0 to 9,

[0114] X is O, S, NR' or CR'R",

[0115] R' and R" are independently hydrogen; deuterium; C1~C 20 Alkyl group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 C2~C containing an aryl group of; and at least one heteroatom of O, N, S, Si and P 20is selected from the group consisting of heterocyclic groups; or R' and R" can be combined with each other to form a ring,

[0116] indicates the position of the bond.}

[0117] Specifically, the compound of the above chemical formula 1 may be any one of the following compounds P-1 to P-128, but is not limited thereto.

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151] In addition, in another aspect, the present invention provides a composition for a phosphorescent light-emitting layer of an organic electric device comprising a mixture of a compound represented by the above chemical formula 1 and a compound represented by the following chemical formula 2.

[0152] <Chemical Formula 2>

[0153]

[0154] In the above chemical formula 2, each symbol can be defined as follows.

[0155] X A , X B and X C are independently of each other CR a or N,

[0156] But, X A , X B and X C At least one of them is N,

[0157] ArA , Ar B and Ar C are independently C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Cycloalkyl group of; and C3~C 60 Aliphatic ring and C6~C 60 A fused ring group of an aromatic ring is selected from the group consisting of;

[0158] The above Ar A , Ar B and Ar C 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.

[0159] The above Ar A , Ar B and Ar C 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.

[0160] The above Ar A , Ar B and Ar CIf it is a cycloalkyl group, preferably C3~C 30 Cycloalkyl group, more preferably C3~C 25 , C3~C 18 or C3~C 12 It may be a cycloalkyl group, and specifically, it may be cyclobutane, cyclopentane, cyclohexane, bicycloheptane, adamantyl, etc.

[0161] The above Ar A , Ar B and Ar C 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.

[0162] L A , L B and L C are independently of each other and are single bonds; C6~C 60 Arylene group; Fluorenylene group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; and C3~C 60 Aliphatic ring and C6~C 60 A fused ring group of an aromatic ring is selected from the group consisting of;

[0163] Above L A , L B and L C 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.

[0164] Above L A , L B and L CIf 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.

[0165] Above L A , L B and L C 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.

[0166] The above R a is hydrogen; or deuterium;

[0167] Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, cycloalkyl group and fused ring 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~C20 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 is one or more deuterium or C6~C 20 It can be further substituted with an aryl group, and these substituents can also combine with each other to form a ring, where the 'ring' refers to 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.

[0168]

[0169] In addition, the present invention comprises the Ar A , Ar B and Ar C At least one of the compositions is a phosphorescent light-emitting layer of an organic electroluminescent device represented by any one of the following chemical formulae Ar-a to Ar-d.

[0170] Chemical formula Ar-a Chemical formula Ar-b

[0171]

[0172] Chemical formula Ar-c Chemical formula Ar-d

[0173]

[0174] {In the above chemical formulas Ar-a to Ar-d,

[0175] Y A , Y B and Y C are O, S, NR independently of each other 1A or CR 1B R 1C and,

[0176] R A , R B , R C, R D , R E , R F , R 1A , R 1B and R 1C are independently the same or different from each other, and independently hydrogen; deuterium; halogen; cyano group; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 20 Heterocyclic group of; 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 adjacent groups can be combined with each other to form a ring,

[0177] ta and tc are independently integers from 0 to 3, tb and td are independently integers from 0 to 4, te is an integer from 0 to 5, tf is an integer from 0 to 7,

[0178] means the position where it is combined.}

[0179]

[0180] The above chemical formula Ar-a can be represented by any one of the following chemical formulas Ar-a-1 to Ar-a-4.

[0181] <Chemical formula Ar-a-1> <Chemical formula Ar-a-2>

[0182]

[0183] <Chemical formula Ar-a-3> <Chemical formula Ar-a-4>

[0184]

[0185] {In the above chemical formulas Ar-a-1 to Ar-a-4, R A, R B , Y A , ta, tb and is as defined in the above chemical formula Ar-a.}

[0186]

[0187] The above chemical formula Ar-b can be represented by the following chemical formula Ar-b-1 or chemical formula Ar-b-2.

[0188] <Chemical formula Ar-b-1> <Chemical formula Ar-b-2>

[0189]

[0190] {In the above chemical formula Ar-b-1 and chemical formula Ar-b-2, R C , R D , Y B , Y C , tc, td and is as defined in the above chemical formula Ar-b.}

[0191]

[0192] The above chemical formula Ar-d can be represented by the following chemical formula Ar-d-1 or chemical formula Ar-d-2.

[0193] <Chemical formula Ar-d-1> <Chemical formula Ar-d-2>

[0194]

[0195] {In the above chemical formula Ar-d-1 and chemical formula Ar-d-2, R F , tf and is as defined in the above chemical formula Ar-d.}

[0196]

[0197] L of the above chemical formula 2 A , L B and L C can be represented by a single bond or any one of the following chemical formulas b-1 to b-13.

[0198] Chemical formula b-1 Chemical formula b-2 Chemical formula b-3 Chemical formula b-4 Chemical formula b-5 Chemical formula b-6

[0199]

[0200] Chemical formula b-7 Chemical formula b-8 Chemical formula b-9 Chemical formula b-10

[0201]

[0202] Chemical formula b-11 Chemical formula b-12 Chemical formula b-13

[0203]

[0204] {In the above chemical formulas b-1 to b-13,

[0205] Z 10 Silver O, S, NR 1D or CR 1E R 1F and,

[0206] a”, c”, d”, e” and i” are each independently an integer from 0 to 4, b” is an integer from 0 to 6, f” and g” are each independently an integer from 0 to 3, h” is an integer from 0 to 2, and j” is an integer of 0 or 1,

[0207] R a1 , R a2 , R a3 , R a4 , R a5 , R a6 , R a7 , R 1D , R 1E and R 1F are independently the same or different from each other, and independently 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; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 20 Alkoxyl group of; and C6~C 20is selected from the group consisting of aryloxy groups; or adjacent groups can be combined with each other to form a ring,

[0208] Z 49 , Z 50 and Z 51 are independently of each other 1G or N,

[0209] But, Z 49 , Z 50 and Z 51 At least one of them is N,

[0210] R 1G is the above R A is identical to the definition of

[0211] means the position where it is combined.}

[0212]

[0213] Specifically, the compound of the above chemical formula 2 may be any one of the following compounds N-1 to N-276, but is not limited thereto.

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284] Preferably, the composition for the phosphorescent light-emitting layer of the organic electric device may be a host for the light-emitting layer.

[0285] In addition, in another aspect, the present invention provides an organic electric device including a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, wherein the organic layer includes a compound represented by the chemical formula 1, or a mixture of a compound represented by the chemical formula 1 and a compound represented by the chemical formula 2, and a composition for a phosphorescent light-emitting layer of the organic electric device.

[0286] 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.

[0287] 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.

[0288] The above recrystallization solvent may preferably be a polar solvent having a polarity index (PI) of 5.5 to 7.2.

[0289] 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.

[0290] 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.

[0291] 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.

[0292] 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.

[0293] 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.

[0294] 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.

[0295] 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.

[0296] 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.

[0297] The above adsorbent may be activated carbon, silica gel, alumina or a material known for adsorption purposes.

[0298] The step of purifying the recovered impurities to a purity of 99.9% or higher may include performing sublimation purification.

[0299]

[0300] Referring to FIG. 1, an organic electric device (100) according to the present invention comprises a first electrode (110), a second electrode (170), and an organic layer comprising a single compound represented by Chemical Formula 1 or two or more compounds 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.

[0301] 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)

[0302] 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 or material for an organic electric device 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 for a light efficiency improvement layer. Preferably, for example, a composition for a phosphorescent light emitting layer of an organic electric device comprising a compound according to Chemical Formula 1 of the present invention, or a mixture of a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2, may be used as a host material for the light emitting layer.

[0303] 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)

[0304] 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.

[0305] 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.

[0306] 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 or a material for an organic electric device as an electron transport material.

[0307] As another specific example, the present invention provides an organic electric device characterized in that the organic layer includes a mixture of the same or different compounds of the compound represented by the chemical formula 1. Preferably, the organic layer includes a light-emitting layer, and the light-emitting layer may include a composition for a phosphorescent light-emitting layer of an organic electric device, which includes a compound represented by the chemical formula 1 or a mixture of a compound represented by the chemical formula 1 and a compound represented by the chemical formula 2.

[0308] In addition, the present invention provides a composition for a phosphorescent light-emitting layer of an organic electric device comprising a compound represented by the above chemical formula 1 or a mixture of a compound represented by the above chemical formula 1 and a compound represented by the above chemical formula 2, and provides an organic electric device comprising the composition.

[0309] In addition, the present invention provides an electronic device including a display device including the organic electric element; and a control unit for driving the display device.

[0310] 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.

[0311]

[0312] Hereinafter, examples of synthesis of compounds represented by the chemical formulas 1 and 2 of the present invention and examples of manufacturing organic electric devices of the present invention will be described in detail by way of examples, but the present invention is not limited to the following examples.

[0313]

[0314] [Synthesis example]

[0315] The compound (final product) represented by chemical formula 1 according to the present invention is synthesized by reacting Sub 1 and Sub 2 as in the following reaction scheme 1, but is not limited thereto.

[0316] <Reaction Scheme 1>

[0317]

[0318] I. Synthesis of Sub1

[0319] Sub1 of the above reaction scheme 1 is synthesized by the reaction path of the following reaction scheme 2, but is not limited thereto.

[0320] <Reaction Formula 2>

[0321]

[0322] 1. Sub1-1 Synthesis Example

[0323]

[0324] Sub1a-1 (25.0 g, 81.38 mmol) was dissolved in DCB (Dichlorobenzene) (200 mL) in a round-bottomed flask, and then Sub1b-1 (18.0 g, 89.52 mmol), K3PO4 (34.5 g, 162.77 mmol), CuI (3.1 g, 16.28 mmol), and EDA (Ethylenediamine) (1.96 g, 32.55 mmol) were added and stirred at 230°C. After the reaction was completed, 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 21.9 g of the product (yield 63%).

[0325] 2. Sub1-9 Synthesis Example

[0326]

[0327] Sub1a-2 (20.0 g, 62.84 mmol) was dissolved in DCB (Dichlorobenzene) (157 mL) in a round-bottomed flask, and then Sub1b-2 (14.4 g, 69.13 mmol), K3PO4 (26.6 g, 125.68 mmol), CuI (2.39 g, 12.57 mmol), and EDA (Ethylenediamine) (1.51 g, 25.14 mmol) were added and stirred at 230°C. After the reaction was completed, 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 15.9 g of the product (yield 57%).

[0328] 3. Sub1-16 Synthesis Example

[0329]

[0330] Sub1a-3 (18.0 g, 58.60 mmol) was dissolved in DCB (Dichlorobenzene) (146 mL) in a round-bottomed flask, and then Sub1b-3 (16.2 g, 64.46 mmol), K3PO4 (24.8 g, 117.19 mmol), CuI (2.23 g, 11.72 mmol), and EDA (Ethylenediamine) (1.41 g, 23.44 mmol) were added and stirred at 230°C. After the reaction was completed, 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 16.80 g of the product (yield 60%).

[0331] 4. Sub1-32 synthesis example

[0332]

[0333] Sub1a-4 (21.0 g, 68.36 mmol) was dissolved in DCB (Dichlorobenzene) (170 mL) in a round-bottomed flask, and then Sub1b-4 (22.7 g, 75.20 mmol), K3PO4 (29.0 g, 136.72 mmol), CuI (2.6 g, 13.67 mmol), and EDA (Ethylenediamine) (1.64 g, 27.34 mmol) were added and stirred at 230°C. After the reaction was completed, 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 23.8 g of the product (yield 66%).

[0334] 5. Sub1-42 Synthesis Example

[0335]

[0336] Sub1a-5 (25.0 g, 81.38 mmol) was dissolved in DCB (Dichlorobenzene) (203 mL) in a round-bottomed flask, and then Sub1b-5 (22.5 g, 89.52 mmol), K3PO4 (34.5 g, 162.7 mmol), CuI (3.1 g, 16.28 mmol), and EDA (Ethylenediamine) (1.9 g, 32.55 mmol) were added and stirred at 230°C. After the reaction was completed, 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 26.0 g of the product (yield 67%).

[0337]

[0338] Compounds belonging to Sub1 may be, but are not limited to, the compounds below, and Table 1 below shows the FD-MS (Field Desorption-Mass Spectrometry) values ​​of compounds belonging to Sub1.

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351] Compound FD-MS Compound FD-MS Sub1-1 m / z = 427.11 (C 30 H 18 Cl N = 427.93) Sub1-2 m / z = 438.18 (C 30 H7D 11 Cl N = 439.00) Sub1-3 m / z = 434.16 (C 30 H 11 D7Cl N = 434.97) Sub1-4 m / z = 477.13 (C 34 H 20 Cl N = 477.99) Sub1-5 m / z = 477.13 (C 34 H 20 Cl N = 477.99) Sub1-6 m / z = 477.13 (C 34 H 20 Cl N = 477.99) Sub1-7 m / z = 527.14 (C 38 H 22 Cl N = 528.05) Sub1-8 m / z = 427.11 (C 30 H 18 Cl N = 427.93) Sub1-9 m / z = 445.23 (C 30 D 18 Cl N = 446.04) Sub1-10 m / z = 477.13 (C34 H 20 ClN=477.99)Sub1-11m / z=477.13(C 34 H 20 ClN=477.99)Sub1-12m / z=477.13(C 34 H 20 ClN=477.99)Sub1-13m / z=538.21(C 38 H 11 D 11 ClN=539.12)Sub1-14m / z=427.11(C 30 H 18 ClN=427.93)Sub1-15m / z=438.18(C 30 H7D 11 ClN=439)Sub1-16m / z=477.13(C 34 H 20 ClN=477.99)Sub1-17m / z=477.13(C 34 H 20 ClN=477.99)Sub1-18m / z=477.13(C 34 H 20 ClN=477.99)Sub1-19m / z=527.14(C 38 H 22 ClN=528.05)Sub1-20m / z=427.11(C 30 H 18 ClN=427.93)Sub1-21m / z=434.16(C 30 H 11 D7ClN=434.97)Sub1-22m / z=438.18(C 30 H7D 11 ClN=439)Sub1-23m / z=477.13(C 34 H 20 ClN=477.99)Sub1-24m / z=477.13(C 34 H 20 ClN=477.99)Sub1-25m / z=477.13(C 34 H 20 ClN=477.99)Sub1-26m / z=527.14(C 38 H 22 ClN=528.05)Sub1-27m / z=427.11(C 30 H18 ClN=427.93)Sub1-28m / z=437.18(C 30 H8D 10 ClN=437.99)Sub1-29m / z=477.13(C 34 H 20 ClN=477.99)Sub1-30m / z=477.13(C 34 H 20 ClN=477.99)Sub1-31m / z=477.13(C 34 H 20 ClN=477.99)Sub1-32m / z=527.14(C 38 H 22 ClN=528.05)Sub1-33m / z=427.11(C 30 H 18 ClN=427.93)Sub1-34m / z=438.18(C 30 H7D 11 ClN=439)Sub1-35m / z=477.13(C 34 H 20 ClN=477.99)Sub1-36m / z=477.13(C 34 H 20 ClN=477.99)Sub1-37m / z=497.25(C 34 D 20 ClN=498.11)Sub1-38m / z=527.14(C 38 H 22 ClN=528.05)Sub1-39m / z=427.11(C 30 H 18 ClN=427.93)Sub1-40m / z=477.13(C 34 H 20 ClN=477.99)Sub1-41m / z=477.13(C 34 H 20 ClN=477.99)Sub1-42m / z=477.13(C 34 H 20 ClN=477.99)Sub1-43m / z=538.21(C 38 H 11 D 11 ClN=539.12)Sub1-44m / z=427.11(C 30 H 18ClN=427.93)Sub1-45m / z=477.13(C 34 H 20 ClN=477.99)Sub1-46m / z=477.13(C 34 H 20 ClN=477.99)Sub1-47m / z=477.13(C 34 H 20 ClN=477.99)Sub1-48m / z=527.14(C 38 H 22 ClN=528.05)

[0352] II. Synthesis of Sub2

[0353] Sub2 of the above reaction scheme 1 is synthesized by the reaction path of the following reaction scheme 3, but is not limited thereto.

[0354] <Reaction Scheme 3> (X is I, Br, or Cl.)

[0355]

[0356] 1. Sub2-1 Synthesis Example

[0357]

[0358] Sub2b-1 (17.4 g, 102.9 mmol) was dissolved in toluene (340 mL) in a round-bottomed flask, and Sub2a-1 (16.0 g, 68.6 mmol), NaOt-Bu (13.1 g, 137.2 mmol), Pd2(dba)3 (1.8 g, 2.0 mmol), and 50 wt% P(t-Bu)3 (2.0 mL, 4.1 mmol) were added, and the mixture was stirred at 110°C. After the reaction was completed, the mixture was extracted with water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 11.6 g of the product (yield 53%).

[0359] 2. Sub2-8 synthesis example

[0360]

[0361] Sub2b-2 (20.27 g, 141.5 mmol) was dissolved in toluene (470 mL) in a round-bottomed flask, and Sub2a-1 (22.0 g, 94.38 mmol), NaOt-Bu (18.1 g, 188.7 mmol), Pd2(dba)3 (2.5 g, 2.8 mmol), and 50 wt% P(t-Bu)3 (2.75 ml, 5.6 mmol) were added, and the mixture was stirred at 110°C. After the reaction was completed, the mixture was extracted with water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 17.0 g of the product (yield 61%).

[0362] 3. Sub2-37 Synthesis Example

[0363]

[0364] Sub2b-3 (11.55 g, 124.0 mmol) was dissolved in toluene (413 mL) in a round-bottomed flask, and Sub2a-2 (24.0 g, 82.7 mmol), NaOt-Bu (15.9 g, 165.4 mmol), Pd2(dba)3 (2.2 g, 2.4 mmol), and 50 wt% P(t-Bu)3 (2.4 ml, 4.9 mmol) were added, and the mixture was stirred at 110°C. After the reaction was completed, the mixture was extracted with water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 16.7 g of the product (yield 67%).

[0365] 4. Sub2-52 Synthesis Example

[0366]

[0367] Sub2b-3 (9.4 g, 100.9 mmol) was dissolved in toluene (336 mL) in a round-bottomed flask, and Sub2a-3 (20.0 g, 67.3 mmol), NaOt-Bu (12.9 g, 134.6 mmol), Pd2(dba)3 (1.8 g, 2.02 mmol), and 50 wt% P(t-Bu)3 (1.96 ml, 4.04 mmol) were added and stirred at 110°C. After the reaction was completed, the mixture was extracted with water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 13.32 g of the product (yield: 64%).

[0368] 5. Sub2-73 Synthesis Example

[0369]

[0370] Sub2b-3 (6.7 g, 72.10 mmol) was dissolved in toluene (240 mL) in a round-bottomed flask, and then Sub2a-4 (19.0 g, 48.06 mmol), NaOt-Bu (9.24 g, 96.13 mmol), Pd2(dba)3 (1.32 g, 1.44 mmol), and 50 wt% P(t-Bu)3 (1.40 ml, 2.88 mmol) were added and stirred at 110°C. After the reaction was completed, the mixture was extracted with water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 10.18 g of the product (yield 52%).

[0371]

[0372] Compounds belonging to Sub2 may be, but are not limited to, the compounds below, and Table 2 below shows the FD-MS values ​​of compounds belonging to Sub2.

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394] Compound FD-MS Compound FD-MS Sub2-1 m / z = 321.15 (C 24 H 19 N=321.42)Sub2-2m / z=371.17(C 28 H 21 N=371.48)Sub2-3m / z=371.17(C 28 H 21 N=371.48)Sub2-4m / z=421.18(C 32 H 23 N=421.54)Sub2-5m / z=254.18(C 18H6D9N=254.38)Sub2-6m / z=300.17(C 22 H 12 D5N=300.42)Sub2-7m / z=295.14(C 22 H 17 N=295.38)Sub2-8m / z=295.14(C 22 H 17 N=295.38)Sub2-9m / z=275.08(C 18 H 13 NS=275.37)Sub2-10m / z=266.14(C 18 H6D7NO=266.35)Sub2-11m / z=259.1(C 18 H 13 NO=259.31)Sub2-12m / z=334.15(C 24 H 18 N2=334.42)Sub2-13m / z=259.21(C 18 HD 14 N=259.41)Sub2-14m / z=295.14(C 22 H 17 N=295.38)Sub2-15m / z=295.14(C 22 H 17 N=295.38)Sub2-16m / z=335.17(C 25 H 21 N=335.45)Sub2-17m / z=321.15(C 24 H 19 N=321.42)Sub2-18m / z=371.17(C 28 H 21 N=371.48)Sub2-19m / z=421.18(C 32 H 23 N=421.54)Sub2-20m / z=269.12(C 20 H 15 N=269.35)Sub2-21m / z=295.14(C 22 H 17 N=295.38)Sub2-22m / z=345.15(C 26 H 19 N=345.44)Sub2-23m / z=311.24(C 22 HD 16N=311.48)Sub2-24m / z=259.1(C 18 H 13 NO=259.31)Sub2-25m / z=384.16(C 28 H 20 N2=384.48)Sub2-26m / z=245.12(C 18 H 15 N=245.32)Sub2-27m / z=345.15(C 26 H 19 N=345.44)Sub2-28m / z=269.12(C 20 H 15 N=269.35)Sub2-29m / z=345.15(C 26 H 19 N=345.44)Sub2-30m / z=371.17(C 28 H 21 N=371.48)Sub2-31m / z=421.18(C 32 H 23 N=421.54)Sub2-32m / z=275.08(C 18 H 13 NS=275.37)Sub2-33m / z=266.14(C 18 H6D7NO=266.35)Sub2-34m / z=389.19(C 28 H 15 D5N2=389.51)Sub2-35m / z=278.18(C 20 H6D9N=278.4)Sub2-36m / z=300.17(C 22 H 12 D5N=300.42)Sub2-37m / z=302.18(C 22 H 10 D7N=302.43)Sub2-38m / z=269.12(C 20 H 15 N=269.35)Sub2-39m / z=329.2(C 24 H 11 D8N=329.47)Sub2-40m / z=407.17(C 31 H 21 N=407.52)Sub2-41m / z=395.17(C 30 H 21N=395.5)Sub2-42m / z=435.27(C 32 H9D 14 N=435.63)Sub2-43m / z=269.12(C 20 H 15 N=269.35)Sub2-44m / z=409.18(C 31 H 23 N=409.53)Sub2-45m / z=409.18(C 31 H 23 N=409.53)Sub2-46m / z=425.12(C 30 H 19 NS=425.55)Sub2-47m / z=359.13(C 26 H 17 NO=359.43)Sub2-48m / z=309.12(C 22 H 15 NO=309.37)Sub2-49m / z=465.23(C 34 H 19 D5N2=465.61)Sub2-50m / z=335.17(C 25 H 21 N=335.45)Sub2-51m / z=306.21(C 22 H6D 11 N=306.45)Sub2-52m / z=309.12(C 22 H 15 NO=309.37)Sub2-53m / z=278.4(C 28 H 20 N2=278.18)Sub2-54m / z=384.48(C 22 H 15 NS=384.16)Sub2-55m / z=325.43(C 24 H 17 N=325.09)Sub2-56m / z=319.41(C 22 H 15 NS=319.14)Sub2-57m / z=325.43(C 18 HD 12 NO=325.09)Sub2-58m / z=271.38(C 24 H 17 N=271.18)Sub2-59m / z=319.41(C 27 H23 N=319.14)Sub2-60m / z=361.49(C 28 H 21 N=361.18)Sub2-61m / z=371.48(C 32 H 21 NO=371.17)Sub2-62m / z=435.53(C 26 H 19 N=435.16)Sub2-63m / z=345.44(C 24 H 17 NS=345.15)Sub2-64m / z=351.47(C 24 H 17 NO=351.11)Sub2-65m / z=335.41(C 22 H 15 NO=335.13)Sub2-66m / z=309.37(C 28 H 15 D5N2=309.12)Sub2-67m / z=389.51(C 26 H 19 N=389.19)Sub2-68m / z=345.44(C 25 H 21 N=345.15)Sub2-69m / z=335.45(C 22 HD 16 N=335.17)Sub2-70m / z=311.48(C 24 H 19 N=311.24)Sub2-71m / z=321.42(C 24 H 19 N=321.15)Sub2-72m / z=321.42(C 31 H 21 N=321.15)Sub2-73m / z=407.52(C 31 H 16 D5N=407.17)Sub2-74m / z=412.2(C 31 H 16 D5N=412.55)Sub2-75m / z=295.14(C 22 H 17 N=295.38)Sub2-76m / z=371.17(C 28 H 21 N=371.48)Sub2-77m / z=334.15(C 22H6D9NS=334.48)Sub2-78m / z=309.12(C 22 H 15 NO=309.37)Sub2-79m / z=335.17(C 25 H 21 N=335.45)Sub2-80m / z=384.16(C 28 H 20 N2=384.48)Sub2-81m / z=361.18(C 27 H 23 N=361.49)Sub2-82m / z=395.17(C 30 H 21 N=395.5)Sub2-83m / z=309.12(C 22 H 15 NO=309.37)Sub2-84m / z=309.12(C 22 H 15 NO=309.37)

[0395] III. Final Product Synthesis

[0396] 1. P-1 synthesis example

[0397]

[0398] Sub2-1 (12.0 g, 37.39 mmol) was dissolved in toluene (186 mL) in a round-bottomed flask, and Sub1-1 (16 g, 37.39 mmol), NaOt-Bu (7.19 g, 74.78 mmol), Pd2(dba)3 (1.03 g, 1.12 mmol), and 50 wt% P(t-Bu)3 (1.09 ml, 2.24 mmol) were added and stirred at 110°C. After the reaction was completed, the mixture was extracted with water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 16.25 g of the product (yield 61%).

[0399] 2. P-24 synthetic example

[0400]

[0401] Sub2-23 (10.34 g, 33.18 mmol) was dissolved in toluene (165 mL) in a round-bottomed flask, and Sub1-9 (14.8 g, 33.18 mmol), NaOt-Bu (6.38 g, 66.36 mmol), Pd2(dba)3 (0.91 g, 1.00 mmol), and 50 wt% P(t-Bu)3 (0.97 ml, 1.99 mmol) were added and stirred at 110°C. After the reaction was completed, the mixture was extracted with water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 13.39 g of the product (yield 56%).

[0402] 3. P-43 synthetic example

[0403]

[0404] Sub2-11 (8.12 g, 31.31 mmol) was dissolved in toluene (156 mL) in a round-bottomed flask, and Sub1-14 (13.4 g, 31.31 mmol), NaOt-Bu (6.02 g, 62.63 mmol), Pd2(dba)3 (0.86 g, 0.94 mmol), and 50 wt% P(t-Bu)3 (0.91 ml, 1.88 mmol) were added and stirred at 110°C. After the reaction was completed, the mixture was extracted with water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 13.44 g of the product (yield: 66%).

[0405] 4. P-55 synthetic example

[0406]

[0407] Sub2-45 (11.39 g, 27.82 mmol) was dissolved in toluene (139 mL) in a round-bottomed flask, and then Sub1-21 (12.1 g, 27.82 mmol), NaOt-Bu (5.35 g, 55.64 mmol), Pd2(dba)3 (0.76 g, 0.83 mmol), and 50 wt% P(t-Bu)3 (0.81 ml, 1.67 mmol) were added and stirred at 110°C. After the reaction was completed, the mixture was extracted with water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 11.68 g of the product (yield 52%).

[0408] 5. P-70 synthetic example

[0409]

[0410] Sub2-54 (15.27 g, 39.73 mmol) was dissolved in toluene (198 mL) in a round-bottomed flask, and Sub1-27 (17 g, 39.73 mmol), NaOt-Bu (7.64 g, 79.45 mmol), Pd2(dba)3 (1.09 g, 1.19 mmol), and 50 wt% P(t-Bu)3 (1.16 ml, 2.38 mmol) were added and stirred at 110°C. After the reaction was completed, the mixture was extracted with water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 19.72 g of the product (yield: 64%).

[0411] 6. P-81 synthetic example

[0412]

[0413] Sub2-60 (13.35 g, 36.92 mmol) was dissolved in toluene (184 mL) in a round-bottomed flask, and Sub1-33 (15.8 g, 36.92 mmol), NaOt-Bu (7.10 g, 73.84 mmol), Pd2(dba)3 (1.01 g, 1.11 mmol), and 50 wt% P(t-Bu)3 (1.07 ml, 2.22 mmol) were added and stirred at 110°C. After the reaction was completed, the mixture was extracted with water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 16.68 g of the product (yield 60%).

[0414] 7. P-86 synthetic example

[0415]

[0416] Sub2-21 (14.13 g, 47.84 mmol) was dissolved in toluene (239 mL) in a round-bottomed flask, and then Sub1-34 (21 g, 47.84 mmol), NaOt-Bu (9.2 g, 95.67 mmol), Pd2(dba)3 (1.31 g, 1.44 mmol), and 50 wt% P(t-Bu)3 (1.39 ml, 2.87 mmol) were added and stirred at 110°C. After the reaction was completed, the mixture was extracted with water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 18.69 g of the product (yield 56%).

[0417] 8. P-94 synthetic example

[0418]

[0419] Sub2-69 (11.02 g, 32.85 mmol) was dissolved in toluene (164 mL) in a round-bottomed flask, and Sub1-36 (15.7 g, 32.85 mmol), NaOt-Bu (6.31 g, 65.69 mmol), Pd2(dba)3 (0.90 g, 0.99 mmol), and 50 wt% P(t-Bu)3 (0.96 ml, 1.97 mmol) were added and stirred at 110°C. After the reaction was completed, the mixture was extracted with water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 16.07 g of the product (yield 63%).

[0420] 9. P-99 synthetic example

[0421]

[0422] Sub2-73 (19.05 g, 46.74 mmol) was dissolved in toluene (233 mL) in a round-bottomed flask, and Sub1-39 (20 g, 46.74 mmol), NaOt-Bu (8.98 g, 93.47 mmol), Pd2(dba)3 (1.28 g, 1.40 mmol), and 50 wt% P(t-Bu)3 (1.36 ml, 2.80 mmol) were added and stirred at 110°C. After the reaction was completed, the mixture was extracted with water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 23.52 g of the product (yield 63%).

[0423] 10. P-121 Synthetic Example

[0424]

[0425] Sub2-9 (10.49 g, 38.09 mmol) was dissolved in toluene (190 mL) in a round-bottomed flask, and Sub1-44 (16.3 g, 38.09 mmol), NaOt-Bu (7.32 g, 76.18 mmol), Pd2(dba)3 (1.05 g, 1.14 mmol), and 50 wt% P(t-Bu)3 (1.11 ml, 2.29 mmol) were added and stirred at 110°C. After the reaction was completed, the mixture was extracted with water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was recrystallized through a silica gel column to obtain 12.95 g of the product (yield 51%).

[0426]

[0427] Meanwhile, the FD-MS values ​​of compounds P-1 to P-128 of the present invention manufactured according to the above-described synthetic examples are as shown in Table 3 below.

[0428] Compound FD-MS Compound FD-MSP-1 m / z = 712.29 (C 54 H 36 N2=712.9)P-2m / z=762.3(C 58 H 38 N2=762.96)P-3m / z=762.3(C 58 H 38 N2=762.96)P-4m / z=812.32(C 62 H 40 N2=813.02)P-5m / z=645.31(C 48 H 23 D9N2=645.85)P-6m / z=691.3(C 52 H 29 D5N2=691.89)P-7m / z=686.27(C 52 H 34 N2=686.86)P-8m / z=697.34(C 52 H 23 D 11 N2=697.93)P-9m / z=666.21(C 48 H 30 N2S=666.84)P-10m / z=657.28(C 48 H 23D7N2O=657.82)P-11m / z=650.24(C 48 H 30 N2O=650.78)P-12m / z=732.33(C 54 H 28 D7N3=732.94)P-13m / z=700.36(C 52 H 20 D 14 N2=700.94)P-14m / z=736.29(C 56 H 36 N2=736.92)P-15m / z=736.29(C 56 H 36 N2=736.92)P-16m / z=826.33(C 63 H 42 N2=827.04)P-17m / z=712.29(C 54 H 36 N2=712.9)P-18m / z=762.3(C 58 H 38 N2=762.96)P-19m / z=762.3(C 58 H 38 N2=762.96)P-20m / z=812.32(C 62 H 40 N2=813.02)P-21m / z=660.26(C 50 H 32 N2=660.82)P-22m / z=686.27(C 52 H 34 N2=686.86)P-23m / z=736.29(C 56 H 36 N2=736.92)P-24m / z=720.49(C 52 D 34 N2=721.07)P-25m / z=666.21(C 48 H 30 N2S=666.84)P-26m / z=650.24(C 48 H 30 N2O=650.78)P-27m / z=650.24(C 48 H 30 N2O=650.78)P-28m / z=775.3(C 58 H 37 N3=775.95)P-29m / z=686.27(C52 H 34 N2=686.86)P-30m / z=786.3(C 60 H 38 N2=786.98)P-31m / z=736.29(C 56 H 36 N2=736.92)P-32m / z=797.37(C 60 H 27 D 11 N2=798.05)P-33m / z=660.26(C 50 H 32 N2=660.82)P-34m / z=736.29(C 56 H 36 N2=736.92)P-35m / z=762.3(C 58 H 38 N2=762.96)P-36m / z=812.32(C 62 H 40 N2=813.02)P-37m / z=661.41(C 48 H7D 25 N2=661.95)P-38m / z=686.27(C 52 H 34 N2=686.86)P-39m / z=686.27(C 52 H 34 N2=686.86)P-40m / z=636.26(C 48 H 32 N2=636.80)P-41m / z=666.21(C 48 H 30 N2S=666.84)P-42m / z=657.28(C 48 H 23 D7N2O=657.82)P-43m / z=650.24(C 48 H 30 N2O=650.78)P-44m / z=780.33(C 58 H 32 D5N3=780.99)P-45m / z=719.33(C 54 H 25 D9N2=719.93)P-46m / z=741.32(C 56 H 31 D5N2=741.95)P-47m / z=743.33(C 56 H29 D7N2=743.96)P-48m / z=760.29(C 58 H 36 N2=760.94)P-49m / z=720.34(C 54 H 28 D8N2=720.94)P-50m / z=798.3(C 61 H 38 N2=798.99)P-51m / z=786.3(C 60 H 38 N2=786.98)P-52m / z=826.41(C 62 H 26 D 14 N2=827.1)P-53m / z=660.26(C 50 H 32 N2=660.82)P-54m / z=800.32(C 61 H 40 N2=801)P-55m / z=807.36(C 61 H 33 D7N2=808.05)P-56m / z=686.27(C 52 H 34 N2=686.86)P-57m / z=816.26(C 60 H 36 N2S=817.02)P-58m / z=761.34(C 56 H 23 D 11 N2O=761.97)P-59m / z=700.25(C 52 H 32 N2O=700.84)P-60m / z=856.36(C 64 H 36 D5N3=857.08)P-61m / z=776.32(C 59 H 40 N2=776.98)P-62m / z=747.36(C 56 H 25 D 11 N2=747.99)P-63m / z=736.29(C 56 H 36 N2=736.92)P-64m / z=786.3(C 60 H 38 N2=786.98)P-65m / z=700.25(C 52 H32 N2O=700.84)P-66m / z=762.3(C 58 H 38 N2=762.96)P-67m / z=762.3(C 58 H 38 N2=762.96)P-68m / z=812.32(C 62 H 40 N2=813.02)P-69m / z=669.31(C 50 H 23 D9N2=669.87)P-70m / z=775.3(C 58 H 37 N3=775.95)P-71m / z=716.23(C 52 H 32 N2S=716.9)P-72m / z=720.33(C 54 H 24 D 10 N2=720.94)P-73m / z=716.23(C 52 H 32 N2S=716.9)P-74m / z=650.24(C 48 H 30 N2O=650.78)P-75m / z=662.31(C 48 H 18 D 12 N2O=662.85)P-76m / z=725.28(C 54 H 35 N3=725.89)P-77m / z=686.27(C 52 H 34 N2=686.86)P-78m / z=736.29(C 56 H 36 N2=736.92)P-79m / z=736.29(C 56 H 36 N2=736.92)P-80m / z=810.3(C 62 H 38 N2=811)P-81m / z=752.32(C 57 H 40 N2=752.96)P-82m / z=762.3(C 58 H 38 N2=762.96)P-83m / z=762.3(C 58 H 38N2=762.96)P-84m / z=826.3(C 62 H 38 N2O=827)P-85m / z=736.29(C 56 H 36 N2=736.92)P-86m / z=697.34(C 52 H 23 D 11 N2=697.93)P-87m / z=686.27(C 52 H 34 N2=686.86)P-88m / z=686.27(C 52 H 34 N2=686.86)P-89m / z=742.24(C 54 H 34 N2S=742.94)P-90m / z=726.27(C 54 H 34 N2O=726.88)P-91m / z=700.25(C 52 H 32 N2O=700.84)P-92m / z=780.33(C 58 H 32 D5N3=780.99)P-93m / z=786.3(C 60 H 38 N2=786.98)P-94m / z=776.32(C 59 H 40 N2=776.98)P-95m / z=772.51(C 56 D 36 N2=773.14)P-96m / z=812.32(C 62 H 40 N2=813.02)P-97m / z=712.29(C 54 H 36 N2=712.9)P-98m / z=762.3(C 58 H 38 N2=762.96)P-99m / z=798.3(C 61 H 38 N2=798.99)P-100m / z=812.32(C 62 H 40 N2=813.02)P-101m / z=636.26(C 48 H 32 N2=636.8)P-102m / z=803.33(C61 H 33 D5N2=804.02)P-103m / z=686.27(C 52 H 34 N2=686.86)P-104m / z=762.3(C 58 H 38 N2=762.96)P-105m / z=725.29(C 52 H 23 D9N2S=725.96)P-106m / z=700.25(C 52 H 32 N2O=700.84)P-107m / z=650.24(C 48 H 30 N2O=650.78)P-108m / z=775.3(C 58 H 37 N3=775.95)P-109m / z=686.27(C 52 H 34 N2=686.86)P-110m / z=736.29(C 56 H 36 N2=736.92)P-111m / z=776.32(C 59 H 40 N2=776.98)P-112m / z=797.37(C 60 H 27 D 11 N2=798.05)P-113m / z=752.32(C 57 H 40 N2=752.96)P-114m / z=762.3(C 58 H 38 N2=762.96)P-115m / z=762.3(C 58 H 38 N2=762.96)P-116m / z=812.32(C 62 H 40 N2=813.02)P-117m / z=636.26(C 48 H 32 N2=636.8)P-118m / z=786.3(C 60 H 38 N2=786.98)P-119m / z=686.27(C 52 H 34 N2=686.86)P-120m / z=693.32(C 52 H27 D7N2=693.9)P-121m / z=666.21(C 48 H 30 N2S=666.84)P-122m / z=750.27(C 56 H 34 N2O=750.9)P-123m / z=700.25(C 52 H 32 N2O=700.84)P-124m / z=775.3(C 58 H 37 N3=775.95)P-125m / z=686.27(C 52 H 34 N2=686.86)P-126m / z=736.29(C 56 H 36 N2=736.92)P-127m / z=736.29(C 56 H 36 N2=736.92)P-128m / z=786.3(C 60 H 38 N2=786.98)

[0429] [Synthesis Example 2]

[0430] The compound represented by the above chemical formula 2 can be prepared by a known synthetic method (named reaction) or by referring to published patent publications, for example, Korean Patent Publication Nos. 2020-0129334, 2022-0055392, 2023-000502, etc., but is not limited thereto.

[0431] Meanwhile, the FD-MS values ​​of compounds N-1 to N-276 of the present invention are as shown in Table 4 below.

[0432] Compound FD-MS Compound FD-MSN-1 m / z = 399.14 (C 27 H 17 N3O=399.45)N-2m / z=415.11(C 27 H 17 N3S=415.51)N-3m / z=474.18(C 33 H 22 N4=474.57)N-4m / z=449.15(C 31 H 19N3O=449.51)N-5m / z=449.15(C 31 H 19 N3O=449.51)N-6m / z=515.15(C 35 H 21 N3S=515.63)N-7m / z=600.23(C 43 H 28 N4=600.73)N-8m / z=499.17(C 35 H 21 N3O=499.57)N-9m / z=551.20(C 39 H 25 N3O=551.65)N-10m / z=567.18(C 39 H 25 N3S=567.71)N-11m / z=702.28(C 51 H 34 N4=702.86)N-12m / z=657.22(C 46 H 31 N3S=657.84)N-13m / z=551.20(C 39 H 25 N3O=551.65)N-14m / z=541.16(C 37 H 23 N3S=541.67)N-15m / z=700.26(C 51 H 32 N4=700.85)N-16m / z=703.21(C 50 H 29 N3S=703.86)N-17m / z=525.18(C 37 H 23 N3O=525.61)N-18m / z=591.18(C 41 H 25 N3S=591.73)N-19m / z=627.24(C 44 H 29 N5=627.75)N-20m / z=524.20(C 37 H 24 N4=524.63)N-21m / z=551.20(C 39 H 25 N3O=551.65)N-22m / z=567.18(C 39 H 25 N3S=567.71)N-23m / z=702.28(C 51H 34 N4=702.86)N-24m / z=474.18(C 33 H 22 N4=474.57)N-25m / z=779.29(C 57 H 37 N3O=779.94)N-26m / z=731.24(C 52 H 33 N3S=731.92)N-27m / z=601.23(C 42 H 27 N5=601.71)N-28m / z=475.17(C 33 H 21 N3O=475.55)N-29m / z=641.21(C 45 H 27 N3O2=641.73)N-30m / z=746.21(C 51 H 30 N4OS=746.89)N-31m / z=716.26(C 51 H 32 N4O=716.84)N-32m / z=681.19(C 47 H 27 N3OS=681.81)N-33m / z=475.17(C 33 H 21 N3O=475.55)N-34m / z=491.15(C 33 H 21 N3S=491.61)N-35m / z=550.22(C 39 H 26 N4=550.67)N-36m / z=525.18(C 37 H 23 N3O=525.61)N-37m / z=475.17(C 33 H 21 N3O=475.55)N-38m / z=491.15(C 33 H 21 N3S=491.61)N-39m / z=704.27(C 49 H 32 N6=704.84)N-40m / z=541.16(C 37 H 23 N3S=541.67)N-41m / z=551.20(C 39 H 25N3O=551.65)N-42m / z=541.16(C 37 H 23 N3S=541.67)N-43m / z=626.25(C 45 H 30 N4=626.76)N-44m / z=676.26(C 49 H 32 N4=676.82)N-45m / z=551.2(C 39 H 25 N3O=551.65)N-46m / z=567.18(C 39 H 25 N3S=567.71)N-47m / z=614.25(C 44 H 30 N4=614.75)N-48m / z=575.17(C 39 H 21 N5O=575.63)N-49m / z=525.18(C 37 H 23 N3O=525.61)N-50m / z=541.16(C 37 H 23 N3S=541.67)N-51m / z=600.23(C 43 H 28 N4=600.73)N-52m / z=625.22(C 45 H 27 N3O=625.73)N-53m / z=525.18(C 37 H 23 N3O=525.61)N-54m / z=591.18(C 41 H 25 N3S=591.73)N-55m / z=600.23(C 43 H 28 N4=600.73)N-56m / z=693.22(C 49 H 31 N3S=693.87)N-57m / z=505.12(C 33 H 19 N3OS=505.60)N-58m / z=641.21(C 45 H 27 N3O2=641.73)N-59m / z=571.12(C 37 H 21 N3S2=571.72)N-60m / z=564.20(C39 H 24 N4O=564.65)N-61m / z=581.16(C 39 H 23 N3OS=581.69)N-62m / z=521.10(C 33 H 19 N3S2=521.66)N-63m / z=489.15(C 33 H 19 N3O2=489.53)N-64m / z=640.23(C 45 H 28 N4O=640.75)N-65m / z=489.15(C 33 H 19 N3O2=489.53)N-66m / z=505.12(C 33 H 19 N3OS=505.60)N-67m / z=580.17(C 39 H 24 N4S=580.71)N-68m / z=564.20(C 39 H 24 N4O=564.65)N-69m / z=489.15(C 33 H 19 N3O2=489.53)N-70m / z=505.12(C 33 H 19 N3OS=505.60)N-71m / z=505.12(C 33 H 19 N3OS=505.60)N-72m / z=639.24(C 45 H 29 N5=639.76)N-73m / z=607.21(C 42 H 29 N3S=607.78)N-74m / z=715.26(C 52 H 33 N3O=715.86)N-75m / z=640.23(C 45 H 28 N4O=640.75)N-76m / z=707.20(C 49 H 29 N3OS=707.85)N-77m / z=591.23(C 42 H 29 N3O=591.71)N-78m / z=617.28(C 45 H35 N3=617.80)N-79m / z=653.25(C 47 H 31 N3O=653.79)N-80m / z=733.22(C 51 H 31 N3OS=733.89)N-81m / z=615.19(C 43 H 25 N3O2=615.69)N-82m / z=681.19(C 47 H 27 N3OS=681.81)N-83m / z=716.29(C 52 H 36 N4=716.89)N-84m / z=690.24(C 49 H 30 N4O=690.81)N-85m / z=641.25(C 46 H 31 N3O=641.77)N-86m / z=693.22(C 49 H 31 N3S=693.87)N-87m / z=690.24(C 49 H 30 N4O=690.81)N-88m / z=631.17(C 43 H 25 N3OS=631.75)N-89m / z=595.14(C 39 H 21 N3O2S=595.68)N-90m / z=659.24(C 45 H 21 D5N4O2=659.76)N-91m / z=637.16(C 42 H 27 N3S2=637.82)N-92m / z=729.25(C 51 H 31 N5O=729.84)N-93m / z=578.17(C 39 H 22 N4O2=578.63)N-94m / z=746.21(C 51 H 30 N4OS=746.89)N-95m / z=681.24(C 48 H 31 N3O2=681.80)N-96m / z=762.19(C 51 H 30N4S2=762.95)N-97m / z=436.17(C 30 H 20 N4=436.52)N-98m / z=437.16(C 29 H 19 N5=437.51)N-99m / z=513.20(C 35 H 23 N5=513.60)N-100m / z=589.23(C 41 H 27 N5=589.70)N-101m / z=486.18(C 34 H 22 N4=486.58)N-102m / z=527.17(C 35 H 21 N5O=527.59)N-103m / z=589.23(C 41 H 27 N5=589.70)N-104m / z=502.18(C 34 H 22 N4O=502.58)N-105m / z=511.20(C 37 H 25 N3=511.63)N-106m / z=563.21(C 39 H 25 N5=563.66)N-107m / z=511.20(C 37 H 25 N3=511.63)N-108m / z=589.23(C 41 H 27 N5=589.70)N-109m / z=513.20(C 35 H 23 N5=513.60)N-110m / z=462.16(C 30 H 18 N6=462.52)N-111m / z=612.21(C 42 H 24 N6=612.70)N-112m / z=499.20(C 36 H 25 N3=499.62)N-113m / z=569.17(C 37 H 23 N5S=569.69)N-114m / z=629.22(C 43 H 27N5O=629.72)N-115m / z=629.22(C 43 H 27 N5O=629.72)N-116m / z=563.21(C 39 H 25 N5=563.66)N-117m / z=565.2(C 37 H 23 N7=565.64)N-118m / z=630.22(C 42 H 26 N6O=630.71)N-119m / z=611.24(C 45 H 29 N3=611.75)N-120m / z=803.29(C 59 H 37 N3O=803.97)N-121m / z=563.20(C 40 H 25 N3O=563.66)N-122m / z=549.22(C 40 H 27 N3=549.68)N-123m / z=449.15(C 31 H 19 N3O=449.51)N-124m / z=579.18(C 40 H 25 N3S=579.72)N-125m / z=435.17(C 31 H 21 N3=435.53)N-126m / z=435.17(C 31 H 21 N3=435.53)N-127m / z=435.17(C 31 H 21 N3=435.53)N-128m / z=435.17(C 31 H 21 N3=435.53)N-129m / z=435.17(C 31 H 21 N3=435.53)N-130m / z=435.17(C 31 H 21 N3=435.53)N-131m / z=435.17(C 31 H 21 N3=435.53)N-132m / z=434.18(C 32 H 22N2=434.54)N-133m / z=511.20(C 37 H 25 N3=511.63)N-134m / z=611.24(C 45 H 29 N3=611.75)N-135m / z=485.19(C 35 H 23 N3=485.59)N-136m / z=511.2(C 37 H 25 N3=511.63)N-137m / z=511.20(C 37 H 25 N3=511.63)N-138m / z=485.19(C 35 H 23 N3=485.59)N-139m / z=434.18(C 32 H 22 N2=434.54)N-140m / z=434.18(C 32 H 22 N2=434.54)N-141m / z=511.20(C 37 H 25 N3=511.63)N-142m / z=561.22(C 41 H 27 N3=561.69)N-143m / z=587.24(C 43 H 29 N3=587.73)N-144m / z=511.20(C 37 H 25 N3=511.63)N-145m / z=511.20(C 37 H 25 N3=511.63)N-146m / z=511.20(C 37 H 25 N3=511.63)N-147m / z=511.20(C 37 H 25 N3=511.63)N-148m / z=587.24(C 43 H 29 N3=587.73)N-149m / z=435.17(C 31 H 21 N3=435.53)N-150m / z=435.17(C 31 H 21 N3=435.53)N-151m / z=435.17(C31 H 21 N3=435.53)N-152m / z=435.17(C 31 H 21 N3=435.53)N-153m / z=435.17(C 31 H 21 N3=435.53)N-154m / z=435.17(C 31 H 21 N3=435.53)N-155m / z=435.17(C 31 H 21 N3=435.53)N-156m / z=434.18(C 32 H 22 N2=434.54)N-157m / z=485.19(C 35 H 23 N3=485.59)N-158m / z=511.2(C 37 H 25 N3=511.63)N-159m / z=511.20(C 37 H 25 N3=511.63)N-160m / z=511.20(C 37 H 25 N3=511.63)N-161m / z=485.19(C 35 H 23 N3=485.59)N-162m / z=511.20(C 37 H 25 N3=511.63)N-163m / z=485.19(C 35 H 23 N3=485.59)N-164m / z=611.24(C 45 H 29 N3=611.75)N-165m / z=511.20(C 37 H 25 N3=511.63)N-166m / z=511.20(C 37 H 25 N3=511.63)N-167m / z=587.24(C 43 H 29 N3=587.73)N-168m / z=587.24(C 43 H 29 N3=587.73)N-169m / z=587.24(C 43 H 29N3=587.73)N-170m / z=561.22(C 41 H 27 N3=561.69)N-171m / z=511.20(C 37 H 25 N3=511.63)N-172m / z=587.24(C 43 H 29 N3=587.73)N-173m / z=485.19(C 35 H 23 N3=485.59)N-174m / z=485.19(C 35 H 23 N3=485.59)N-175m / z=485.19(C 35 H 23 N3=485.59)N-176m / z=485.19(C 35 H 23 N3=485.59)N-177m / z=485.19(C 35 H 23 N3=485.59)N-178m / z=535.20(C 39 H 25 N3=535.65)N-179m / z=485.19(C 35 H 23 N3=485.59)N-180m / z=485.19(C 35 H 23 N3=485.59)N-181m / z=561.22(C 41 H 27 N3=561.69)N-182m / z=561.22(C 41 H 27 N3=561.69)N-183m / z=561.22(C 41 H 27 N3=561.69)N-184m / z=637.25(C 47 H 31 N3=637.79)N-185m / z=561.22(C 41 H 27 N3=561.69)N-186m / z=561.22(C 41 H 27 N3=561.69)N-187m / z=637.25(C 47 H 31 N3=637.79)N-188m / z=637.25(C47 H 31 N3=637.79)N-189m / z=637.25(C 47 H 31 N3=637.79)N-190m / z=485.19(C 35 H 23 N3=485.59)N-191m / z=485.19(C 35 H 23 N3=485.59)N-192m / z=611.24(C 45 H 29 N3=611.75)N-193m / z=485.19(C 35 H 23 N3=485.59)N-194m / z=485.19(C 35 H 23 N3=485.59)N-195m / z=611.24(C 45 H 29 N3=611.75)N-196m / z=485.19(C 35 H 23 N3=485.59)N-197m / z=485.19(C 35 H 23 N3=485.59)N-198m / z=561.22(C 41 H 27 N3=561.69)N-199m / z=485.19(C 35 H 23 N3=485.59)N-200m / z=485.19(C 35 H 23 N3=485.59)N-201m / z=611.24(C 45 H 29 N3=611.75)N-202m / z=611.24(C 45 H 29 N3=611.75)N-203m / z=485.19(C 35 H 23 N3=485.59)N-204m / z=485.19(C 35 H 23 N3=485.59)N-205m / z=485.19(C 35 H 23 N3=485.59)N-206m / z=485.19(C 35 H 23N3=485.59)N-207m / z=535.20(C 39 H 25 N3=535.65)N-208m / z=535.2(C 39 H 25 N3=535.65)N-209m / z=585.22(C 43 H 27 N3=585.71)N-210m / z=535.2(C 39 H 25 N3=535.65)N-211m / z=585.22(C 43 H 27 N3=585.71)N-212m / z=585.22(C 43 H 27 N3=585.71)N-213m / z=611.24(C 45 H 29 N3=611.75)N-214m / z=611.24(C 45 H 29 N3=611.75)N-215m / z=585.22(C 43 H 27 N3=585.71)N-216m / z=611.24(C 45 H 29 N3=611.75)N-217m / z=687.27(C 51 H 33 N3=687.85)N-218m / z=611.24(C 45 H 29 N3=611.75)N-219m / z=511.20(C 37 H 25 N3=511.63)N-220m / z=611.24(C 45 H 29 N3=611.75)N-221m / z=561.22(C 41 H 27 N3=561.69)N-222m / z=587.24(C 43 H 29 N3=587.73)N-223m / z=663.27(C 49 H 33 N3=663.82)N-224m / z=713.28(C 53 H 35 N3=713.88)N-225m / z=575.20(C41 H 25 N3O=575.67)N-226m / z=601.22(C 43 H 27 N3O=601.71)N-227m / z=700.26(C 51 H 32 N4=700.85)N-228m / z=701.25(C 51 H 31 N3O=701.83)N-229m / z=667.21(C 47 H 29 N3S=667.83)N-230m / z=541.16(C 37 H 23 N3S=541.67)N-231m / z=612.23(C 44 H 28 N4=612.74)N-232m / z=562.22(C 40 H 26 N4=562.68)N-233m / z=689.26(C 49 H 31 N5=689.82)N-234m / z=639.24(C 45 H 29 N5=639.76)N-235m / z=701.25(C 51 H 31 N3O=701.83)N-236m / z=631.17(C 43 H 25 N3OS=631.75)N-237m / z=625.22(C 45 H 27 N3O=625.73)N-238m / z=591.18(C 41 H 25 N3S=591.73)N-239m / z=687.27(C 51 H 33 N3=687.85)N-240m / z=701.25(C 51 H 31 N3O=701.83)N-241m / z=619.30(C 45 H 37 N3=619.81)N-242m / z=601.25(C 44 H 31 N3=601.75)N-243m / z=667.23(C 47 H29 N3O2=667.77)N-244m / z=540.24(C 39 H 20 D5N3=540.68)N-245m / z=521.17(C 35 H 21 F2N3=521.57)N-246m / z=510.18(C 36 H 22 N4=510.60)N-247m / z=652.23(C 46 H 28 N4O=652.76)N-248m / z=527.24(C 38 H 29 N3=527.67)N-249m / z=535.20(C 39 H 25 N3=535.65)N-250m / z=535.20(C 39 H 25 N3=535.65)N-251m / z=535.20(C 39 H 25 N3=535.65)N-252m / z=535.20(C 39 H 25 N3=535.65)N-253m / z=587.24(C 43 H 29 N3=587.73)N-254m / z=612.23(C 44 H 28 N4=612.74)N-255m / z=561.22(C 41 H 27 N3=561.69)N-256m / z=687.27(C 51 H 33 N3=687.85)N-257m / z=663.27(C 49 H 33 N3=663.82)N-258m / z=601.22(C 43 H 27 N3O=601.71)N-259m / z=617.19(C 43 H 27 N3S=617.77)N-260m / z=752.29(C 55 H 36 N4=752.92)N-261m / z=651.23(C 47 H 29N3O=651.77)N-262m / z=677.25(C 49 H 31 N3O=677.81)N-263m / z=541.16(C 37 H 23 N3S=541.67)N-264m / z=750.28(C 55 H 34 N4=750.91)N-265m / z=707.24(C 50 H 33 N3S=707.90)N-266m / z=651.23(C 47 H 29 N3O=651.77)N-267m / z=617.19(C 43 H 27 N3S=617.77)N-268m / z=667.21(C 47 H 29 N3S=667.83)N-269m / z=631.17(C 43 H 25 N3OS=631.75)N-270m / z=767.26(C 55 H 33 N3O2=767.89)N-271m / z=647.15(C 43 H 25 N3S2=647.81)N-272m / z=690.24(C 49 H 30 N4O=690.81)N-273m / z=575.2(C 41 H 25 N3O=575.67)N-274m / z=614.21(C 43 H 26 N4O=614.71)N-275m / z=575.2(C 41 H 25 N3O=575.67)N-276m / z=549.18(C 39 H 23 N3O=549.63)

[0433] Meanwhile, although the above has been described with respect to exemplary synthetic examples of the present invention or references represented by Chemical Formula 1 and Chemical Formula 2, 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.

[0434]

[0435] organic light-emitting diodes

[0436] [Example 1] Red organic light-emitting device (phosphorescent host)

[0437] An organic electroluminescent device was fabricated using the compound obtained through synthesis as a light-emitting host material of the light-emitting layer according to a conventional method. First, a N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (hereinafter, 2-TNATA) film was vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a 50 nm thick hole injection layer, and then 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, NPB) was vacuum-deposited on the hole injection layer to a thickness of 80 nm as a hole transport compound to form a hole transport layer. After forming the hole transport layer, the compound P-2 of the present invention represented by the chemical formula 1 and the compound N-128 of the present invention represented by the chemical formula 2 were used as hosts at a weight ratio of (5:5) on the upper portion of the hole transport layer, and (piq)2Ir(acac) was doped as a dopant material at a weight ratio of 95:5 to deposit a light-emitting layer with a thickness of 40 nm. Subsequently, (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum (hereinafter referred to as BAlq) was vacuum-deposited with a thickness of 10 nm as a hole blocking layer, and bis(10-hydroxybenzo[h]quinolinato)beryllium (hereinafter referred to as BeBq2) was deposited with a thickness of 20 nm as an electron transport layer. Afterwards, LiF, a halogenated alkali metal, was deposited as an electron injection layer with a thickness of 0.2 nm, and Al was then deposited with a thickness of 150 nm and used as a cathode, thereby manufacturing an organic light emitting device.

[0438]

[0439] [Example 2] to [Example 34]

[0440] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds of the present invention described in Table 5 below were used instead of the compounds P-2 and N-128 of the present invention as phosphorescent host materials.

[0441]

[0442] [Comparative Example 1] to [Comparative Example 5]

[0443] An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compounds A to E were used instead of Compound P-2 of the present invention as a phosphorescent host material.

[0444] [Comparative Compound A] [Comparative Compound B] [Comparative Compound C]

[0445]

[0446] [Comparative Compound D] [Comparative Compound E]

[0447]

[0448] The organic electroluminescence devices manufactured in this way were applied with a forward bias DC voltage and the electroluminescence (EL) characteristics were measured using a PR-650 from Photoresearch, and 2500 cd / m 2 The T95 lifespan was measured using a lifespan measuring device manufactured by Maxscience at a reference luminance. Table 5 below shows the results of the device fabrication and evaluation.

[0449] 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.

[0450] 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.

[0451] Compound 1 Compound 2 Driving voltage (V) Current (mA / cm) 2) Efficiency (cd / A) T (95) Comparative Example 1 Comparative Compound A Compound (N-128) 5.2 1 1.6 2 1.6 9 3.1 Comparative Example 2 Comparative Compound B Compound (N-128) 5.3 1 1.7 2 1.3 9 1.6 Comparative Example 3 Comparative Compound C Compound (N-128) 5.3 1 2.0 2 0.8 9 0.3 Comparative Example 4 Comparative Compound D Compound (N-128) 5.4 1 2.8 1 9.6 9 5.7 Comparative Example 5 Comparative Compound E Compound (N-128) 5.111.222.495.3 Example 1 Compound (P-2) Compound (N-128) 4.78.728.7105.6 Example 2 Compound (P-11) Compound (N-128) 4.88.828.3108.6 Example 3 Compound (P-27) Compound (N-128) 4.78.828.5111.3 Example 4 Compound (P-37) Compound (N-128) 4.78.529.5112.1 Example 5 Compound (P-40) Compound (N-128) 4.68.629 .2109.6 Example 6 Compound (P-41) Compound (N-128) 4.68.728.7111.6 Example 7 Compound (P-43) Compound (N-128) 4.78.728.8112.7 Example 8 Compound (P-49) Compound (N-128) 4.68.828.3110.3 Example 9 Compound (P-50) Compound (N-128) 4.79.426.7105.4 Example 10 Compound (P-66) Compound (N-128) 4.79.227.1104.4 Example 11 Compound (P -75) Compound (N-128) 4.89.2 27.0 109.9 Example 12 Compound (P-90) Compound (N-128) 4.78.8 28.3 106.2 Example 13 Compound (P-101) Compound (N-128) 4.89.0 27.9 104.9 Example 14 Compound (P-102) Compound (N-128) 5.09.3 26.9 104.9 Example 15 Compound (P-107) Compound (N-128) 4.89.1 27.6 107.8 Example 16 Compound (P-109) Compound (N -128)4.88.828.5103.9Example 17 Compound (P-117) Compound (N-128)4.89.027.7102.3Example 18 Compound (P-2) Compound (N-274)4.89.027.7108.7Example 19 Compound (P-11) Compound (N-274)4.89.127.4111.8Example 20 Compound (P-27) Compound (N-274)4.89.127.6114.6Example 21 Compound (P-37) Compound (N-274)4.78.728.6115.5 Example 22 Compound (P-40) Compound (N-274) 4.7 8.8 28.3 112.9 Example 23 Compound (P-41) Compound (N-274) 4.6 9.0 27.8 114.9 Example 24 Compound (P-43) Compound (N-274) 4.7 9.0 27.9 116.1 Example 25 Compound (P-49) Compound (N-274) 4.7 9.1 27.4 113.6 Example 26 Compound (P-50) Compound (N-274) 4.8 9.7 25.8 108.5 Example 27 Compound (P-66) Compound (N-274) 4.7 9.5 26.2 107.6 Example 28 Compound (P-75) Compound (N -274)4.89.526.2113.2Example 29 Compound (P-90) Compound (N-274)4.89.127.4109.4Example 30 Compound (P-101) Compound (N-274)4.89.327.0108.0Example 31 Compound (P-102) Compound (N-274)5.09.6 26.1108.0 Example 32 Compound (P-107) Compound (N-274) 4.99.4 26.7 111.1 Example 33 Compound (P-109) Compound (N-274) 4.99.127.6 107.0 Example 34 Compound (P-117) Compound (N-274) 4.99.3 26.9 105.4.

[0452] As can be seen in Table 5 above, when a red organic electroluminescent device is manufactured using the material for an organic electroluminescent device of the present invention as a phosphorescent host material, the compound of the present invention exhibits remarkable characteristics in device performance compared to the case where comparative compounds A to E were used, and particularly, exhibits excellent characteristics in terms of efficiency.

[0453] As can be seen above, when forming a host for a light-emitting layer by mixing multiple compounds, it can be confirmed that there is a significant difference in characteristics depending on the type of the first and second compounds. Similarly, there are differences in driving voltage, efficiency, and lifespan depending on the type of the second compound.

[0454] Comparing the compounds of the present invention with comparative compounds A to C, the present invention differs in that chrysene is substituted as a substituent of carbazole, whereas comparative compounds A to C are substituted with phenanthrene or triphenylene. This can be confirmed through Table 6 below.

[0455] Table 6 below shows the energy levels of comparative compounds A to C and compound P-40 of the present invention measured using the DFT Method (B3LYP / 6-31g(D)) of the Gaussian program.

[0456] Comparative Compound A Comparative Compound B Comparative Compound CP-40T12.582.652.652.46

[0457] As can be seen from the results in Table 6 above, it can be confirmed that the T1 of compound P-40 of the present invention is lower than that of comparative compounds A to C.

[0458] This means that the red dopant has the lowest T1 among phosphorescent R / G / B, and the lowest T1 energy gap with the red dopant. In other words, it simultaneously plays a role in transferring excitons from the host P-40 to the dopant and blocking excitons moving from the dopant to the hole transport layer, resulting in a very significant difference in efficiency.

[0459] In addition, when the comparative compound D and the compound of the present invention are compared, the comparative compound D has a structure in which two carbazoles are bonded, whereas the compound of the present invention has an amino group bonded to the 2nd position of the carbazole, which results in a large difference in the physical properties or morphology of the compounds (especially the HOMO level), and this results in a difference in the overall performance of the compounds.

[0460] Finally, when comparing the comparative compound E with the compound of the present invention, there is a difference in that the comparative compound E has a composition in which carbazole is not substituted, but the compound of the present invention includes carbazole.

[0461] Table 7 below describes the calculated Reorganization Energy values ​​of comparative compounds E and P-40.

[0462] The RE ratio values ​​listed in Table 7 below are RE hole and RE elec After calculating RE hole / RE elec It means the calculated value.

[0463] Comparative compound EP-40RE ratio 0.5451.079

[0464] If the above Table 7 is explained in detail, it can be seen that the RE ratio value of the compound P-40 of the present invention is greater than that of the comparative compound E. This means the correlation between hole mobility and electron mobility, and RE elec A higher value means a decrease in the RE ratio.

[0465] That is, RE elec The higher the RE ratio, the lower the electron mobility, which results in an increase in the luminescent region. Therefore, the wider the luminescent region, the lower the efficiency. On the other hand, the higher the RE ratio, the higher the electron mobility, which results in a narrower luminescent region, which results in an increase in efficiency. Therefore, the compound of the present invention appears to have higher efficiency than the comparative compound E.

[0466] Therefore, it appears that the efficiency is dramatically increased due to the synergistic effect that occurs by substituting a specific substituent as in the present invention.

[0467] 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, rather than 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.

[0468] 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, A ring is C 10 is an aryl group, R 1 , R 2 and R 3 are independently of each other, the same or different, 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; 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 groups; or adjacent multiple R 2 R's or multiple R's 3 They can combine with each other to form rings, Ar 1 and Ar 2 are independently C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; and C3~C 60 Aliphatic ring and C6~C 60 A fused ring group of an aromatic ring is selected from the group consisting of; a is an integer from 0 to 11, b is an integer from 0 to 4, c is an integer from 0 to 3, Here, the aryl group and heterocyclic group are deuterium; C1~C 20 Alkyl group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 Aryl group of; C2~C 20 may be further substituted with one or more substituents selected from the group consisting of heterocyclic groups; 2. A compound characterized in that, in paragraph 1, the chemical formula 1 is represented by any one of the following chemical formulas 3 to 10. <Chemical Formula 3> <Chemical Formula 4> <Chemical Formula 5> <Chemical Formula 6> <Chemical Formula 7> <Chemical Formula 8> <Chemical Formula 9> <Chemical Formula 10> {In the above chemical formulas 3 to 10, R 1 , R 2 , R 3 , Ar 1 , Ar 2 , b and c are as defined in claim 1 above, a' is an integer from 0 to 11.

3. In the first paragraph, the Ar 1 and Ar 2 A compound characterized by being represented by any one of the following chemical formulas a-1 to a-15 <Chemical Formula A-1> <Chemical Formula A-2> <Chemical Formula A-3> <Chemical Formula A-4> <Chemical Formula A-5> <Chemical Formula A-6> <Chemical Formula A-7> <Chemical Formula A-8> <Chemical Formula A-9> <Chemical Formula A-10> <Chemical Formula A-11> <Chemical Formula a1-12> <Chemical Formula a-13> <Chemical Formula a-14> <Chemical Formula a-15> {In the above chemical formulas a-1 to a-15, R 4 are each identical or different and independently of each other deuterium; C6~C 20 Aryl group of; and C6~C substituted with deuterium 20 aryl group of; selected from the group consisting of, or adjacent multiple R 4 They can combine with each other to form rings, d and f are independently integers from 0 to 5, e is an integer from 0 to 4, g and i are independently integers from 0 to 7, h is an integer from 0 to 9, X is O, S, NR' or CR'R", R' and R" are independently hydrogen; deuterium; C1~C 20 Alkyl group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 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; or R' and R" can be combined with each other to form a ring, indicates the position of the bond.} 4. In the first paragraph, a compound characterized in that the compound represented by the chemical formula 1 is any one of the following compounds P-1 to P-128.

5. A composition for a phosphorescent light-emitting layer of an organic electric device comprising a mixture of a compound represented by the chemical formula 1 according to Article 1 and a compound represented by the chemical formula 2 below. <Chemical Formula 2> {In the above chemical formula 2, X A , X B and X C are independently of each other CR a or N, But, X A , X B and X C At least one of them is N, Ar A , Ar B and Ar C are independently C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Cycloalkyl group of; and C3~C 60 Aliphatic ring and C6~C 60 A fused ring group of an aromatic ring is selected from the group consisting of; L A , L B and L C are independently of each other and are single bonds; C6~C 60 Arylene group; Fluorenylene group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; and C3~C 60 Aliphatic ring and C6~C 60 A fused ring group of an aromatic ring is selected from the group consisting of; The above R a is hydrogen; or deuterium; Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, cycloalkyl group and fused ring 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 is one or more deuterium or C6~C 20 It can be further substituted with an aryl group, and these substituents can also combine with each other to form a ring, where the 'ring' refers to 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.

6. In paragraph 5, the Ar A , Ar B and Ar C A composition for a phosphorescent light-emitting layer of an organic electric device, characterized in that at least one of the following chemical formulae Ar-a to Ar-d is represented by any one of the following chemical formulae: Chemical formula Ar-a Chemical formula Ar-b Chemical formula Ar-c Chemical formula Ar-d {In the above chemical formulas Ar-a to Ar-d, Y A , Y B and Y C are independently of each other O, S, NR 1A or CR 1B R 1C and, R A , R B , R C , R D , R E , R F , R 1A , R 1B and R 1C are independently the same or different from each other, and independently hydrogen; deuterium; halogen; cyano group; 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 groups; or adjacent groups can be combined with each other to form a ring, ta and tc are independently integers from 0 to 3, tb and td are independently integers from 0 to 4, te is an integer from 0 to 5, tf is an integer from 0 to 7, means the position of joining.} 7. A composition for a phosphorescent light-emitting layer of an organic electric device, characterized in that the compound represented by the chemical formula 2 in the fifth paragraph is any one of the following compounds N-1 to N-276.

8. A composition for a phosphorescent light-emitting layer of an organic electric device, characterized in that the composition in claim 5 is a host for a light-emitting layer.

9. In an organic electric device including a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, An organic electric device characterized in that the organic layer comprises the compound of claim 1 or the composition of claim 5.

10. An organic electric device according to claim 9, further comprising a light efficiency improvement layer formed on at least one surface of the first electrode and the second electrode, the surface being opposite to the organic layer.

11. 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 the first electrode.

12. An organic electric device according to claim 11, characterized in that the organic layer further includes a charge generation layer formed between the two or more stacks.

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

14. An electronic device according to claim 13, wherein 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.

15. 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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