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 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 or chemical formula 3.

[0015] <Chemical Formula 2> <Chemical Formula 3>

[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 composition 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] Each symbol in the drawing is as follows.

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

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

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

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

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

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

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

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

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

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

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

[0033] ST1: 1st stack ST2: 2nd stack

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

[0035] Additionally, terms such as first, second, A, B, (a), (b), etc. may be used to describe components of the present invention. These terms are only intended to distinguish the components from other components, and the nature, order, or sequence of the components are not limited by the terms. When it is described that a component is "connected," "coupled," or "connected" to another component, it should be understood that the component may be directly connected or connected to the other component, but another component may also be "connected," "coupled," or "connected" between each component.

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

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

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

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

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

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

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

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

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

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

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

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

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

[0049]

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

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

[0052]

[0053] The term "spiro compound" used in the present invention has a "spiro union," and a spiro union means a connection formed by two rings sharing only one atom. In this case, the atom shared between the two rings is called a "spiro atom," and depending on the number of spiro atoms contained in a compound, these are called "monospiro-," "dicepiro-," and "trispiro-" compounds, respectively.

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

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

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

[0057] Also, unless explicitly stated otherwise, the term "substituted" in the term "substituted or unsubstituted" used in the present invention means deuterium, halogen, amino group, nitrile group, nitro group, C1~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.

[0058] In this specification, the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc., which are exemplified as examples of each symbol and its substituent, may be described as the 'group name reflecting the valence', or may be described as the 'parent compound name'. For example, in the case of 'phenanthrene', which is a type of aryl group, the name of the group may be described by distinguishing the valence, such as 'phenanthryl' for the monovalent 'group' and 'phenantrylene' for the divalent group, but it may also be described as the parent compound name 'phenanthrene' regardless of the valence. Similarly, in the case of pyrimidine, it may be described as 'pyrimidine' regardless of the valence, or it may be described as the 'group name' of the corresponding valence, such as pyrimidinyl group for monovalent and pyrimidinylene for divalent. In addition, in this specification, numbers or alphabets indicating positions may be omitted when describing the compound name or substituent name. For example, pyrido[4,3-d]pyrimidine can be written as pyridopyrimidine, benzofuro[2,3-d]pyrimidine can be written as benzofuropyrimidine, 9,9-dimethyl-9H-fluorene can be written as dimethylfluorene, etc. Accordingly, both benzo[g]quinoxaline and benzo[f]quinoxaline can be written as benzoquinoxaline.

[0059] Additionally, unless explicitly stated otherwise, the chemical formulas used in the present invention are applied in the same manner as the substituent definitions by the index definitions of the chemical formulas below.

[0060]

[0061] Here, if a is an integer of 0, the substituent R 1 is absent, and if a is an integer of 1, there is one substituent R 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.

[0062]

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

[0064] [Example of ortho-position]

[0065]

[0066] [Example of meta-position]

[0067]

[0068] [Example of para-location]

[0069]

[0070]

[0071] 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).

[0072]

[0073] Hereinafter, a compound according to one aspect of the present invention, a composition for an organic electric device, and an organic electric device including the same will be described.

[0074]

[0075] The present invention provides a compound represented by the following chemical formula 1.

[0076] <Chemical Formula 1>

[0077]

[0078] In the above chemical formula 1, each symbol can be defined as follows.

[0079] R 1 and R 2 are each the same or different from each other, and are independently hydrogen; or deuterium; and a plurality of R 1 Kiri or R 2 They cannot combine with each other to form rings,

[0080] a is an integer from 0 to 8, b is an integer from 0 to 7,

[0081] Ar1 is substituted or unsubstituted C6~C 24 Aryl group of; or C2~C containing at least one heteroatom among substituted or unsubstituted O, N, S, Si and P 60 is a heterocyclic group; and

[0082] If the above Ar1 is an aryl group, C6~C 24 Aryl group of, preferably C6~C 20 Aryl group, C6~C 18 Aryl group, C6~C 16 Aryl group, C6~C 14 Aryl group, C6~C 12 Aryl group, C6~C 10 Aryl group, C6 aryl group, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc., and when Ar1 is a heterocyclic group, C2~C 60 A heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2~C 24 Heterocyclic group, C2~C 20 Heterocyclic group, C2~C 18 Heterocyclic group, C2~C 16 Heterocyclic group, C2~C 12 Heterocyclic group of C 12It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0083] Here, in the case of Ar1 being a substituted aryl group and a substituted heterocyclic group, each independently represents hydrogen; deuterium; C6~C 20 Aryl group of; or C6~C substituted with deuterium 20 It indicates that it is further substituted with an aryl group.

[0084]

[0085] Ar2 is substituted or unsubstituted C6~C 12 Aryl group; and preferably substituted or unsubstituted C6~C 10 It may be an aryl group, a substituted or unsubstituted C6 aryl group.

[0086] L1 and L2 are each the same or different and independently a single bond; substituted or unsubstituted C6~C 60 Arylene group of; or C2~C containing at least one heteroatom among substituted or unsubstituted O, N, S, Si and P 60 is a heterocyclic group; and

[0087] When L1 and L2 are arylene groups, C6~C 60 Arylene group, preferably C6~C 30 Arylene group, C6~C 20 Arylene group, C6~C 18 Arylene group, C6~C 16 Arylene group, C6~C 14 Arylene group, C6~C 12 Arylene group, C6~C 10 An arylene group may be a C6 arylene group, such as phenyl, biphenyl, terphenyl, naphthalene, or phenanthrene.

[0088] When L1 and L2 are heterocyclic groups, C2~C 60 Heterocyclic group, C2~C 20 Heterocyclic group, C2~C 18 Heterocyclic group, C2~C 16 Heterocyclic group, C2~C 12 Heterocyclic group of C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0089] Here, in the case where Ar2, L1 and L2 are substituted aryl groups, substituted arylene groups and substituted heterocyclic groups, the substituents are each independently hydrogen; or deuterium;

[0090]

[0091] In addition, the present invention includes a compound represented by the chemical formula 1 below, or chemical formula 1-1 or chemical formula 1-2.

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

[0093]

[0094] {In the above chemical formulas 1-1 and 1-2, R 1 , R 2 , Ar1, Ar2, L1, L2, a and b are as defined above.}

[0095]

[0096] In addition, the present invention includes a compound in which Ar1 is represented by any one of the following chemical formulas Ar-1 to Ar-17.

[0097] Ar-1 Ar-2 Ar-3 Ar-4

[0098]

[0099] Ar-5 Ar-6 Ar-7 Ar-8

[0100]

[0101] Ar-9 Ar-10 Ar-11 Ar-12

[0102]

[0103] Ar-13 Ar-14 Ar-15 Ar-16

[0104]

[0105]

[0106] Ar-17

[0107]

[0108] In the above chemical formulas Ar-1 to Ar-17, R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are identical or different from each other, and independently of each other, hydrogen; deuterium; C6~C 20 Aryl group of; or C6~C substituted with deuterium 20 aryl group of; and,

[0109]

[0110] c is an integer from 0 to 5, d, f and g are integers from 0 to 7, e is integers from 0 to 9, h is integers from 0 to 8,

[0111] * indicates the position where it binds to L1.

[0112]

[0113] The present invention provides a compound in which Ar2 is represented by any one of the following chemical formulas Ar2-1 to Ar2-6.

[0114] Ar2-1 Ar2-2 Ar2-3 Ar2-4

[0115]

[0116] Ar2-5 Ar2-6

[0117]

[0118] In the above chemical formulas Ar2-1 to Ar2-6, R 9 , R 10 , R 11 and R 12 are identical or different from each other, and independently of each other, hydrogen; deuterium; C6~C 20 Aryl group of; or C6~C substituted with deuterium 20 aryl group of; and,

[0119] i is an integer from 0 to 5, j is an integer from 0 to 7, k is an integer from 0 to 4, l is an integer from 0 to 5,

[0120] * indicates the position where Ar2 is bonded in chemical formula 1.

[0121]

[0122] The present invention provides a compound in which L1 and L2 are selected from any one of the following chemical formulas L-1 to L-10.

[0123] L-1 L-2 L-3 L-4

[0124]

[0125] L-5 L-6 L-7 L-8

[0126]

[0127] In the above chemical formulas L-1 to L-8, R 13 , R 14 , R 15 , R 16 and R 17 are identical or different from each other, and independently of each other, hydrogen; deuterium; C6~C 20 Aryl group of; or C6~C substituted with deuterium 20 aryl group of; and,

[0128] m is an integer from 0 to 4, n, o and p are any integer from 0 to 6, q is any integer from 0 to 7,

[0129] * indicates the positions where L1 and L2 are each bonded in chemical formula 1.

[0130]

[0131] As another example, the present invention provides a compound in which at least one deuterium is substituted in the compound represented by the above chemical formula 1.

[0132]

[0133] Specifically, the compound represented by the above chemical formula 1 may be any one of the following chemical formulas P-1 to P-136, but is not limited thereto.

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170] A composition for an organic electric device comprising the compound of claim 1; and a compound represented by the following chemical formula 2 or chemical formula 3;

[0171] <Chemical Formula 2> <Chemical Formula 3>

[0172]

[0173] {In the above chemical formula 2 and chemical formula 3,

[0174] L 11 , L 12 , L 13 and L14 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;

[0175] Above L 11 , L 12 , L 13 and L 14 If it is an arylene group, preferably C6~C 30 Arylene group, more preferably C6~C 24 , C6~C 18 , or C6~C 12 It may be an arylene group, such as phenylene, biphenylene, naphthylene, terphenylene, anthracenylene, phenanthrenylene, etc.

[0176] Above L 11 , L 12 , L 13 and L 14 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, pyridazine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, benzocarbazole, naphthobenzofuran, naphthobenzothiophene, etc.

[0177] Above L 11 , L 12 , L 13 and L 14 If it is a fusion ring, preferably C3~C 30Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 24 Aliphatic ring and C6~C 24 It may be a fused ring group of an aromatic ring.

[0178] Ar 11 , Ar 12 and Ar 13 are independently C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C3~C 60 Aliphatic ring group; 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;

[0179] The above Ar 11 , Ar 12 and Ar 13 If it is an aryl group, preferably C6~C 30 Aryl group of, more preferably C6~C 24 , C6~C 18 , or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, etc.

[0180] The above Ar 11 , Ar 12 and Ar 13 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, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0181] The above Ar 11 , Ar 12 and Ar 13 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 24 Aliphatic ring and C6~C 24 It may be a fused ring group of an aromatic ring.

[0182] The above Ar 11 , Ar 12 and Ar 13 If it is an alkyl group, preferably C1~C 30 It may be an alkyl group of, more preferably C1~C 24 , C1~C 18 , or C1~C 12 It may be an alkyl group.

[0183] The above Ar 11 , Ar 12 and Ar 13 If it is an alkoxyl group, preferably C1~C 24 It may be an alkoxyl group.

[0184] The above Ar 11 , Ar 12 and Ar 13 If it is an aryloxy group, preferably C6~C 24 It may be an aryloxy group.

[0185] Ar 14 is C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 A fused ring group of an aromatic ring; and -L'-NR'R"; is selected from the group consisting of,

[0186] The above Ar 14 If it is an aryl group, preferably C6~C 30 Aryl group of, more preferably C6~C 24 , C6~C 18 , or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.

[0187] The above Ar 14 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, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0188] The above Ar 14 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 24 Aliphatic ring and C6~C 24 It may be a fused ring group of an aromatic ring.

[0189] Z is O, S, CR 51 R 52 or NR 53 And,

[0190] Ring A is C6~C 20 is an aryl group,

[0191] L' is a single bond; C6~C 60 Arylene group; Fluorenylene group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; and C3~C 60 is selected from the group consisting of aliphatic rings;

[0192] If the above L' is an arylene group, preferably C6~C 30 Arylene group, more preferably C6~C 24 , C6~C 18 , or C6~C 12 It may be an arylene group, such as phenylene, biphenylene, naphthylene, terphenylene, anthracenylene, phenanthrenylene, etc.

[0193] If the above L' is a heterocyclic group, it is preferably C2~C 30 A heterocyclic group, more preferably C6~C 25 , C6~C 18 , or C6~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyridazine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, benzocarbazole, naphthobenzofuran, naphthobenzothiophene, etc.

[0194] If the above L' is an aliphatic ring group, preferably C3~C 30 Aliphatic ring group, more preferably C3~C 24 It may be an aliphatic ring.

[0195] R 51 , R 52 , R 53 , R' and R" are the above Ar 11 is identical to the definition of , or R 51 and R 52can combine with each other to form spy rings,

[0196] R 21 and R 22 are identical or different from each other, and independently of each other, hydrogen; deuterium; halogen; cyano group; C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 An aryloxy group of R is selected from the group consisting of, or a plurality of adjacent R 21 R's or multiple R's 22 They can combine with each other to form rings,

[0197] The above R 21 and R 22 If it is an aryl group, preferably C6~C 30 Aryl group of, more preferably C6~C 24 , C6~C 18 , or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.

[0198] The above R 21 and R 22 If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C6~C 25 , C6~C 18 , or C6~C 12It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0199] The above R 21 and R 22 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 24 Aliphatic ring and C6~C 24 It may be a fused ring group of an aromatic ring.

[0200] The above R 21 and R 22 If it is an alkyl group, preferably C1~C 30 It may be an alkyl group of C6~C, more preferably 24 , C6~C 18 , or C6~C 12 It may be an alkyl group.

[0201] The above R 21 and R 22 If it is an alkoxyl group, preferably C1~C 24 It may be an alkoxyl group.

[0202] The above R 21 and R 22 If it is an aryloxy group, preferably C6~C 24 It may be an aryloxy group.

[0203]

[0204] aa and ab are integers from 0 to 4, independently of each other,

[0205] Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 Alkylthio group of; C1~C 20 Alkoxyl group of; 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 Cycloalkyl group of; C7~C 20 Arylalkyl group of; C8~C 20 Aryl alkenyl group of; and -L'-NR'R"; may be further substituted with one or more substituents selected from the group consisting of, and further, the hydrogen of these substituents may be further substituted with one or more deuteriums, and further, these substituents may be combined with each other to form a ring, wherein the 'ring' refers to a group consisting of 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.

[0206]

[0207] Preferably, the composition for the organic electric element may be a host for the light-emitting layer.

[0208] The above chemical formula 2 can be represented by the following chemical formulas 2-1 to 2-3.

[0209] <Chemical Formula 2-1> <Chemical Formula 2-2>

[0210]

[0211] <Chemical Formula 2-3>

[0212]

[0213] {In the above chemical formulas 2-1 to 3-3,

[0214] Ar 12 , Ar 13 , L 11 , L 12 and L 13 is the same as defined in the above chemical formula 2,

[0215] X 11 , X 12 and X 13 is the same as the definition of Z in the above chemical formula 3,

[0216] R 23 , R 24 , R 25 , R 26 , R 27 and R 28 are the same or different from each other, and independently represent hydrogen; 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; 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 Cycloalkyl group of; C7~C 20 Arylalkyl group of; and C8~C 20 is selected from the group consisting of arylalkenyl groups; or adjacent multiple R 23 R's or multiple R's 24 R's or multiple R's 25 R's or multiple R's 26 R's or multiple R's 27 R's or multiple R's 28 They can combine with each other to form rings,

[0217] ac, af and ag are each independently an integer from 0 to 4, and ad, ae and ah are each independently an integer from 0 to 3.

[0218] The above chemical formula 3 can be represented by the following chemical formulas 3-1 to 3-6.

[0219] <Chemical Formula 3-1> <Chemical Formula 3-2>

[0220]

[0221] <Chemical Formula 3-3> <Chemical Formula 3-4>

[0222]

[0223] <Chemical Formula 3-5> <Chemical Formula 3-6>

[0224]

[0225] {In the above chemical formulas 3-1 to 3-6,

[0226] Z, Ar 14 , L 14 , R 21 , R 22 , aa and ab are the same as defined in the above chemical formula 3,

[0227]

[0228] R 29 is the above R 21 Same as the definition of , or adjacent multiple R 29 They can combine with each other to form rings,

[0229] ai is an integer between 0 and 2.}

[0230]

[0231] The above chemical formula 3 can be represented by any one of the following chemical formulas 3-7 to 3-9.

[0232] <Chemical Formula 3-7> <Chemical Formula 3-8>

[0233]

[0234] <Chemical Formula 3-9>

[0235]

[0236] {In the above chemical formulas 3-7 to 3-9,

[0237] Z, A ring, Ar 14 , L 14 , R 22 and ab are the same as defined in the above chemical formula 3,

[0238] R 30 Silver is the above R 21 Same as the definition of , or adjacent multiple R 30 They can combine with each other to form rings,

[0239] aj is an integer from 0 to 6.}

[0240] The above chemical formula 3 can be represented by the following chemical formulas 3-10 to 3-12.

[0241] <Chemical Formula 3-10> <Chemical Formula 3-11>

[0242]

[0243] <Chemical Formula 3-12>

[0244]

[0245] {In the above chemical formulas 3-10 to 3-12,

[0246] Z, A ring, Ar 14 , L 14 , R 21 and aa are the same as defined in the above chemical formula 3,

[0247] R 31 Silver is the above R 21 Same as the definition of , or adjacent multiple R 31 They can combine with each other to form rings,

[0248] ak is an integer from 0 to 6.}

[0249]

[0250] The above chemical formula 3 can be represented by the following chemical formulas 3-13 to 3-18.

[0251] <Chemical Formula 3-13> <Chemical Formula 3-14>

[0252]

[0253] <Chemical Formula 3-15> <Chemical Formula 3-16>

[0254]

[0255] <Chemical Formula 3-17> <Chemical Formula 3-18>

[0256]

[0257] {In the above chemical formulas 3-13 to 3-18,

[0258] Z, Ar 14 , L 14 , R 21 , R 22 , aa and ab are the same as defined in the above chemical formula 3,

[0259]

[0260] R 29 , R 30 and R 31 Silver is the above R 21 Same as the definition of , or adjacent multiple R 29 R's or multiple R's 30 R's or multiple R's 31 They can combine with each other to form rings,

[0261] ai is an integer from 0 to 2, and aj and ak are integers from 0 to 6, independently of each other.

[0262]

[0263] The above chemical formula 3 can be represented by the following chemical formula 3-19.

[0264] <Chemical Formula 3-19>

[0265]

[0266] {In the above chemical formula 3-19,

[0267] Ar 14 , L 14 , R 53 , R 22 and ab are the same as defined in the above chemical formula 3,

[0268] R 29 and R 30 Silver is the above R 21 Same as the definition of , or adjacent multiple R 29 R's or multiple R's 30 They can combine with each other to form rings,

[0269] ai is an integer from 0 to 2, and aj is an integer from 0 to 6.

[0270]

[0271] Specifically, the compound represented by the above chemical formula 2 may be a compound represented by any one of the following compounds N-1 to N-128, but is not limited thereto.

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305] Specifically, the compound represented by the above chemical formula 3 may be represented by any one of the following compounds S-1 to S-120, but is not limited thereto.

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337] In addition, in another aspect, the present invention provides an organic electric device comprising a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, wherein the organic layer comprises a compound represented by the chemical formula 1 or a composition for an organic electric device.

[0338] In addition, in another aspect, the present invention provides a method for reusing a compound represented by the above chemical formula 1, comprising: a step 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; a step of removing impurities from an unrefined organic light-emitting material recovered from a deposition apparatus; a step of recovering the removed impurities; and a step of purifying the recovered impurities to a purity of 99.9% or higher.

[0339] 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.

[0340] The above recrystallization solvent may preferably be a polar solvent having a polarity index (PI) of 5.5 to 7.2.

[0341]

[0342] 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.

[0343] 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.

[0344] 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.

[0345] 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.

[0346] 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.

[0347] 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.

[0348] 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.

[0349] 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.

[0350] The above adsorbent may be activated carbon, silica gel, alumina or a material known for adsorption purposes.

[0351] The step of purifying the recovered impurities to a purity of 99.9% or higher may include performing sublimation purification.

[0352]

[0353] 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.

[0354] 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)

[0355] 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 compound according to Chemical Formula 1 of the present invention, or a composition for an organic electric device comprising a mixture of a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2 or 3, may be used as a host material for the light emitting layer.

[0356] 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)

[0357] 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.

[0358] 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.

[0359] 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 the composition for an organic electric device as an electron transport material.

[0360] 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 an organic electric device including 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 or 3.

[0361]

[0362] In addition, the present invention provides a composition for an organic electric device comprising 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 or 3, and provides an organic electric device comprising the composition.

[0363] 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.

[0364] 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.

[0365]

[0366] Hereinafter, examples of synthesis of compounds represented by the chemical formulas 1, 2 and 3 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.

[0367]

[0368] [Synthesis example]

[0369] The compound (final product) represented by chemical formula 1 according to the present invention can be synthesized by reacting Sub 1 and Sub 2 as in the following reaction scheme 1, but is not limited thereto.

[0370] <Reaction Scheme 1>

[0371]

[0372]

[0373] I. Example of Sub 1

[0374] Compounds belonging to Sub 1 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 Sub 1.

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398] Compound FD-MS Compound FD-MS Sub1-1 m / z = 317.07 (C 19 H 12ClN3=317.78)Sub1-2m / z=324.12(C 19 H5D7ClN3=324.82)Sub1-3m / z=317.07(C 19 H 12 ClN3=317.78)Sub1-4m / z=367.09(C 23 H 14 ClN3=367.84)Sub1-5m / z=367.09(C 23 H 14 ClN3=367.84)Sub1-6m / z=367.09(C 23 H 14 ClN3=367.84)Sub1-7m / z=393.10(C 25 H 16 ClN3=393.87)Sub1-8m / z=393.10(C 25 H 16 ClN3=393.87)Sub1-9m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-10m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-11m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-12m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-13m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-14m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-15m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-16m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-17m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-18m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-19m / z=443.12(C29 H 18 ClN3=443.93)Sub1-20m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-21m / z=393.10(C 25 H 16 ClN3=393.87)Sub1-22m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-23m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-24m / z=493.13(C 33 H 20 ClN3=493.99)Sub1-25m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-26m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-27m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-28m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-29m / z=322.10(C 19 H7D5ClN3=322.81)Sub1-30m / z=329.15(C 19 D 12 ClN3=329.85)Sub1-31m / z=483.11(C 31 H 18 ClN3O=483.95)Sub1-32m / z=483.11(C 31 H 18 ClN3O=483.95)Sub1-33m / z=483.11(C 31 H 18 ClN3O=483.95)Sub1-34m / z=483.11(C 31 H 18 ClN3O=483.95)Sub1-35m / z=483.11(C 31 H 18 ClN3O=483.95)Sub1-36m / z=483.11(C 31 H18 ClN3O=483.95)Sub1-37m / z=483.11(C 31 H 18 ClN3O=483.95)Sub1-38m / z=483.11(C 31 H 18 ClN3O=483.95)Sub1-39m / z=483.11(C 31 H 18 ClN3O=483.95)Sub1-40m / z=483.11(C 31 H 18 ClN3O=483.95)Sub1-41m / z=483.11(C 31 H 18 ClN3O=483.95)Sub1-42m / z=483.11(C 31 H 18 ClN3O=483.95)Sub1-43m / z=499.09(C 31 H 18 ClN3S=500.02)Sub1-44m / z=499.09(C 31 H 18 ClN3S=500.02)Sub1-45m / z=499.09(C 31 H 18 ClN3S=500.02)Sub1-46m / z=499.09(C 31 H 18 ClN3S=500.02)Sub1-47m / z=499.09(C 31 H 18 ClN3S=500.02)Sub1-48m / z=499.09(C 31 H 18 ClN3S=500.02)Sub1-49m / z=499.09(C 31 H 18 ClN3S=500.02)Sub1-50m / z=499.09(C 31 H 18 ClN3S=500.02)Sub1-51m / z=499.09(C 31 H 18 ClN3S=500.02)Sub1-52m / z=499.09(C 31 H 18 ClN3S=500.02)Sub1-53m / z=499.09(C 31 H18 ClN3S=500.02)Sub1-54m / z=499.09(C 31 H 18 ClN3S=500.02)Sub1-55m / z=406.10(C 25 H 15 ClN4=406.87)Sub1-56m / z=406.10(C 25 H 15 ClN4=406.87)Sub1-57m / z=482.13(C 31 H 19 ClN4=482.97)Sub1-58m / z=482.13(C 31 H 19 ClN4=482.97)Sub1-59m / z=483.11(C 31 H 18 ClN3O=483.95)Sub1-60m / z=499.09(C 31 H 18 ClN3S=500.02)Sub1-61m / z=483.11(C 31 H 18 ClN3O=483.95)Sub1-62m / z=609.16(C 41 H 24 ClN3O=610.11)Sub1-63m / z=559.15(C 37 H 22 ClN3O=560.05)Sub1-64m / z=559.15(C 37 H 22 ClN3O=560.05)Sub1-65m / z=407.08(C 25 H 14 ClN3O=407.86)Sub1-66m / z=407.08(C 25 H 14 ClN3O=407.86)Sub1-67m / z=407.08(C 25 H 14 ClN3O=407.86)Sub1-68m / z=407.08(C 25 H 14 ClN3O=407.86)Sub1-69m / z=407.08(C 25 H 14 ClN3O=407.86)Sub1-70m / z=407.08(C 25 H14 ClN3O=407.86)Sub1-71m / z=407.08(C 25 H 14 ClN3O=407.86)Sub1-72m / z=407.08(C 25 H 14 ClN3O=407.86)Sub1-73m / z=393.10(C 25 H 16 ClN3=393.87)Sub1-74m / z=393.10(C 25 H 16 ClN3=393.87)Sub1-75m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-76m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-77m / z=393.10(C 25 H 16 ClN3=393.87)Sub1-78m / z=393.10(C 25 H 16 ClN3=393.87)Sub1-79m / z=499.09(C 31 H 18 ClN3S=500.02)Sub1-80m / z=499.09(C 31 H 18 ClN3S=500.02)Sub1-81m / z=499.09(C 31 H 18 ClN3S=500.02)Sub1-82m / z=499.09(C 31 H 18 ClN3S=500.02)Sub1-83m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-84m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-85m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-86m / z=443.12(C 29 H 18 ClN3=443.93)Sub1-87m / z=483.11(C 31 H18 ClN3O=483.95)Sub1-88m / z=483.11(C 31 H 18 ClN3O=483.95)

[0399] Ⅱ. Example of Sub 2

[0400] Compounds belonging to Sub 2 may be, but are not limited to, the compounds below, and Table 2 below shows the FD-MS values ​​of compounds belonging to Sub 2.

[0401]

[0402]

[0403]

[0404]

[0405] Compound FD-MS Compound FD-MS Sub2-1 m / z = 380.19 (C 26 H 25 BO2=380.29)Sub2-2m / z=388.24 (C 26 H 17 D8BO2=388.34)Sub2-3m / z=385.23 (C 26 H 20 D5BO2=385.32)Sub2-4m / z=393.28 (C 26 H 12 D 13 BO2=393.37)Sub2-5m / z=430.21 (C 30 H 27 BO2=430.35)Sub2-6m / z=430.21 (C 30 H 27 BO2=430.35)Sub2-7m / z=456.23 (C 32 H 29 BO2=456.39)Sub2-8m / z=456.23 (C 32 H 29 BO2=456.39)Sub2-9m / z=456.23 (C 32 H 29 BO2=456.39)

[0406] Final product synthesis example

[0407] P-1 Synthesis Example

[0408]

[0409]

[0410] 1) Synthesis of Sub 1-1

[0411] 2,4-dichloro-6-phenyl-1,3,5-triazine (52.58 g, 232.57 mmol), naphthalen-2-ylboronic acid (20 g, 116.29 mmol), Pd(PPh3)4 (4.03 g, 3.49 mmol), and K2CO3 (32.14 g, 232.57 mmol) were dissolved in 258 mL of THF and 129 mL of H2O, and stirred at 60°C for 8 hours. After completion of the reaction, the mixture was extracted with CH2Cl2 and water, and the organic layer was treated with MgSO4, concentrated, and then applied to silica gel, column chromatography, and recrystallization were performed to obtain 28.4 g of the product (yield: 60%).

[0412] 2) Synthesis of P-1

[0413] Sub 1-1 (28 g, 88.11 mmol), Sub 2-1 (35.18 g, 92.52 mmol), Pd(PPh3)4 (3.06 g, 2.64 mmol), and NaOH (7.05 g, 176.22 mmol) were dissolved in 195 mL of toluene, 9.7 mL of EtOH, and 97 mL of H2O in a round-bottomed flask, and stirred at 120 °C. Upon completion of the reaction, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The resulting organic material was purified by silica gel column chromatography and recrystallization to obtain 28.31 g of the product (yield: 60%).

[0414]

[0415] P-5 Synthetic Example

[0416]

[0417]

[0418] 1) Synthesis of Sub 1-5

[0419] 2,4-dichloro-6-(naphthalen-2-yl)-1,3,5-triazine (64.22 g, 232.57 mmol), naphthalen-2-ylboronic acid (20 g, 116.29 mmol), Pd(PPh3)4 (4.03g, 3.49 mmol), K2CO3 (32.14 g, 232.57 mmol) were dissolved in 258 mL of THF and 129 mL of H2O, and then 21.3 g of the product (yield: 45%) was obtained using the synthetic method of Sub 1-1 above.

[0420] 2) Synthesis of P-5

[0421] Sub 1-5 (21 g, 57.09 mmol), Sub 2-1 (22.80 g, 59.94 mmol), Pd(PPh3)4 (1.98 g, 1.71 mmol), NaOH (4.57 g, 114.18 mmol) were dissolved in 126 mL of toluene, 6.3 mL of EtOH, and 63 mL of H2O in a round-bottom flask, and then 21.4 g of the product (yield: 70%) was obtained using the synthetic method of P-1 above.

[0422]

[0423] P-15 Synthetic Example

[0424]

[0425]

[0426] 1) Synthesis of Sub 1-15

[0427] 2,4-dichloro-6-phenyl-1,3,5-triazine (38.30 g, 169.41 mmol), [1,2'-binaphthalen]-6'-ylboronic acid (25 g, 84.7 mmol), Pd(PPh3)4 (2.94 g, 2.54 mmol), K2CO3 (23.41 g, 169.41 mmol) were dissolved in 188 mL of THF and 94 mL of H2O, and 17.9 g of the product (yield: 52%) was obtained using the synthetic method of Sub 1-1 above.

[0428] 2) Synthesis of P-15

[0429] Sub 1-5 (17 g, 38.29 mmol), Sub 2-1 (15.29 g, 40.21 mmol), Pd(PPh3)4 (1.33 g, 1.15 mmol), NaOH (3.06 g, 76.59 mmol) were dissolved in 85.1 mL of toluene, 4.2 mL of EtOH, and 42 mL of H2O in a round-bottom flask, and 13.1 g of the product (yield: 64%) was obtained using the synthetic method of P-1 above.

[0430]

[0431] P-31 composite example

[0432]

[0433]

[0434] 1) Synthesis of Sub 1-26

[0435] 2,4-dichloro-6-(6-phenylnaphthalen-2-yl)-1,3,5-triazine (122.87 g, 348.86 mmol), naphthalen-2-ylboronic acid (30 g, 174.43 mmol), Pd(PPh3)4 (6.05 g, 5.23 mmol), K2CO3 (48.22 g, 348.86 mmol) were dissolved in 387 mL of THF and 193 mL of H2O, and 34.8 g of the product (yield: 45%) was obtained using the synthetic method of Sub 1-1 above.

[0436] 2) Synthesis of P-31

[0437] Sub 1-26 (30 g, 67.58 mmol), Sub 2-1 (26.98 g, 70.96 mmol), Pd(PPh3)4 (2.34 g, 2.03 mmol), NaOH (5.41 g, 135.16 mmol) were dissolved in 150 mL of toluene, 7.5 mL of EtOH, and 75 mL of H2O in a round-bottom flask, and then 26.8 g of the product (yield: 60%) was obtained using the synthetic method of P-1 above.

[0438]

[0439] P-38 composite example

[0440]

[0441]

[0442] Sub 1-1 (28 g, 88.11 mmol), Sub 2-3 (35.18 g, 92.52 mmol), Pd(PPh3)4 (3.06 g, 2.64 mmol), NaOH (7.05 g, 176.22 mmol) were dissolved in 195 mL of toluene, 9.7 mL of EtOH, and 97 mL of H2O in a round-bottom flask, and then 28.31 g of the product (yield: 60%) was obtained using the synthesis method of P-1 above.

[0443]

[0444] P-50 composite example

[0445]

[0446]

[0447] 1) Synthesis of Sub 1-39

[0448] 2,4-dichloro-6-(8-phenyldibenzo[b,d]furan-1-yl)-1,3,5-triazine (100.3 g, 255.83 mmol), naphthalen-2-ylboronic acid (22 g, 127.91 mmol), Pd(PPh3)4 (4.44 g, 3.84 mmol), and K2CO3 (35.36 g, 255.83 mmol) were dissolved in 284 mL of THF and 142 mL of H2O, and then 34.04 g of the product (yield: 55%) was obtained using the synthetic method of Sub 1-1 above.

[0449] 2) Synthesis of P-50

[0450] Sub 1-39 (34 g, 70.26 mmol), Sub 2-1 (28.05 g, 73.77 mmol), Pd(PPh3)4 (2.44 g, 2.11 mmol), NaOH (5.62 g, 140.51 mmol) were dissolved in 156 mL of toluene, 7.8 mL of EtOH, and 78 mL of H2O in a round-bottom flask, and then 33.5 g of the product (yield: 68%) was obtained using the synthetic method of P-1 above.

[0451]

[0452] P-96 composite example

[0453]

[0454]

[0455] 1) Synthesis of Sub 1-7

[0456] 2,4-dichloro-6-phenyl-1,3,5-triazine (27.57 g, 121.97 mmol), (4-(naphthalen-1-yl)phenyl)boronic acid (18 g, 60.99 mmol), Pd(PPh3)4 (2.11 g, 1.83 mmol), K2CO3 (16.86 g, 121.97 mmol) were dissolved in 135 mL of THF and 67 mL of H2O, and 16.1 g of the product (yield: 65%) was obtained using the synthetic method of Sub 1-1 above.

[0457] 2) Synthesis of P-96

[0458] Sub 1-7 (16 g, 40.62 mmol), Sub 2-1 (16.22 g, 42.65 mmol), Pd(PPh3)4 (1.41 g, 1.22 mmol), NaOH (3.25 g, 81.25 mmol) were dissolved in 90 mL of toluene, 4.5 mL of EtOH, and 45 mL of H2O in a round-bottom flask, and 16.1 g of the product (yield: 60%) was obtained using the synthetic method of P-1 above.

[0459]

[0460] P-103 Synthetic Example

[0461]

[0462]

[0463] 1) Synthesis of Sub 1-14

[0464] 2,4-dichloro-6-phenyl-1,3,5-triazine (39.43 g, 174.41 mmol), [1,2'-binaphthalen]-7'-ylboronic acid (26 g, 87.20 mmol), Pd(PPh3)4 (3.02 g, 2.62 mmol), K2CO3 (24.11 g, 174.41 mmol) were dissolved in 193 mL of THF and 96 mL of H2O, and 16.6 g of the product (yield: 43%) was obtained using the synthetic method of Sub 1-1 above.

[0465] 2) Synthesis of P-103

[0466] Sub 1-14 (16 g, 36.04 mmol), Sub 2-5 (16.29 g, 37.84 mmol), Pd(PPh3)4 (1.25 g, 1.08 mmol), NaOH (2.88 g, 72.08 mmol) were dissolved in 80 mL of toluene, 4 mL of EtOH, and 40 mL of H2O in a round-bottom flask, and then 16.6 g of the product (yield: 65%) was obtained using the synthetic method of P-1 above.

[0467]

[0468] Compound FD-MS Compound FD-MSP-1 m / z = 535.20 (C 39 H 25 N3=535.65)P-2m / z=542.25 (C 39 H 18 D7N3=542.69)P-3m / z=535.20 (C 39 H 25 N3=535.65)P-4m / z=585.22 (C 43 H 27 N3=585.71)P-5m / z=585.22 (C 43 H 27 N3=585.71)P-6m / z=585.22 (C 43 H 27 N3=585.71)P-7m / z=611.24 (C 45 H 29 N3=611.75)P-8m / z=611.24 (C 45 H 29 N3=611.75)P-9m / z=661.25 (C 49 H 31 N3=661.81)P-10m / z=661.25 (C 49 H 31 N3=661.81)P-11m / z=661.25 (C 49 H 31 N3=661.81)P-12m / z=661.25 (C 49 H 31 N3=661.81)P-13m / z=661.25 (C49 H 31 N3=661.81)P-14m / z=661.25 (C 49 H 31 N3=661.81)P-15m / z=661.25 (C 49 H 31 N3=661.81)P-16m / z=661.25 (C 49 H 31 N3=661.81)P-17m / z=661.25 (C 49 H 31 N3=661.81)P-18m / z=661.25 (C 49 H 31 N3=661.81)P-19m / z=661.25 (C 49 H 31 N3=661.81)P-20m / z=661.25 (C 49 H 31 N3=661.81)P-21m / z=585.22 (C 43 H 27 N3=585.71)P-22m / z=585.22 (C 43 H 27 N3=585.71)P-23m / z=585.22 (C 43 H 27 N3=585.71)P-24m / z=585.22 (C 43 H 27 N3=585.71)P-25m / z=585.22 (C 43 H 27 N3=585.71)P-26m / z=611.24 (C 45 H 29 N3=611.75)P-27m / z=661.25 (C 49 H 31 N3=661.81)P-28m / z=661.25 (C 49 H 31 N3=661.81)P-29m / z=711.27 (C 53 H 33 N3=711.87)P-30m / z=661.25 (C 49 H 31 N3=661.81)P-31m / z=661.25 (C 49 H 31N3=661.81)P-32m / z=661.25 (C 49 H 31 N3=661.81)P-33m / z=661.25 (C 49 H 31 N3=661.81)P-34m / z=543.26(C 39 H 17 D8N3=543.70)P-35m / z=550.30(C 39 H 10 D 15 N3=550.74)P-36m / z=543.26(C 39 H 17 D8N3=543.70)P-37m / z=593.27(C 43 H 19 D8N3=593.76)P-38m / z=540.24(C 39 H 20 D5N3=540.68)P-39m / z=540.24(C 39 H 20 D5N3=540.68)P-40m / z=545.27(C 39 H 15 D 10 N3=545.71)P-41m / z=560.36 (C 39 D 25 N3=560.80)P-42m / z=701.25 (C 51 H 31 N3O=701.83)P-43m / z=701.25 (C 51 H 31 N3O=701.83)P-44m / z=701.25 (C 51 H 31 N3O=701.83)P-45m / z=701.25 (C 51 H 31 N3O=701.83)P-46m / z=701.25 (C 51 H 31 N3O=701.83)P-47m / z=701.25 (C 51 H 31 N3O=701.83)P-48m / z=701.25 (C 51 H 31 N3O=701.83)P-49m / z=701.25 (C 51 H31 N3O=701.83)P-50m / z=701.25 (C 51 H 31 N3O=701.83)P-51m / z=701.25 (C 51 H 31 N3O=701.83)P-52m / z=701.25 (C 51 H 31 N3O=701.83)P-53m / z=701.25 (C 51 H 31 N3O=701.83)P-54m / z=717.22 (C 51 H 31 N3S=717.89)P-55m / z=717.22 (C 51 H 31 N3S=717.89)P-56m / z=717.22 (C 51 H 31 N3S=717.89)P-57m / z=717.22 (C 51 H 31 N3S=717.89)P-58m / z=717.22 (C 51 H 31 N3S=717.89)P-59m / z=717.22 (C 51 H 31 N3S=717.89)P-60m / z=717.22 (C 51 H 31 N3S=717.89)P-61m / z=717.22 (C 51 H 31 N3S=717.89)P-62m / z=717.22 (C 51 H 31 N3S=717.89)P-63m / z=717.22 (C 51 H 31 N3S=717.89)P-64m / z=717.22 (C 51 H 31 N3S=717.89)P-65m / z=717.22 (C 51 H 31 N3S=717.89)P-66m / z=624.23 (C 45 H 28 N4=624.75)P-67m / z=624.23 (C 45 H 28N4=624.75)P-68m / z=700.26 (C 51 H 32 N4=700.84)P-69m / z=700.26 (C 51 H 32 N4=700.84)P-70m / z=701.25 (C 51 H 31 N3O=701.83)P-71m / z=717.22 (C 51 H 31 N3S=717.89)P-72m / z=701.25 (C 51 H 31 N3O=701.83)P-73m / z=827.29 (C 61 H 37 N3O=827.99)P-74m / z=777.28 (C 57 H 35 N3O=777.93)P-75m / z=777.28 (C 57 H 35 N3O=777.93)P-76m / z=625.22 (C 45 H 27 N3O=625.73)P-77m / z=625.22 (C 45 H 27 N3O=625.73)P-78m / z=625.22 (C 45 H 27 N3O=625.73)P-79m / z=625.22 (C 45 H 27 N3O=625.73)P-80m / z=625.22 (C 45 H 27 N3O=625.73)P-81m / z=625.22 (C 45 H 27 N3O=625.73)P-82m / z=625.22 (C 45 H 27 N3O=625.73)P-83m / z=625.22 (C 45 H 27 N3O=625.73)P-84m / z=611.24 (C 45 H 29 N3=611.75)P-85m / z=611.24 (C 45 H 29N3=611.75)P-86m / z=661.25 (C 49 H 31 N3=661.81)P-87m / z=661.25 (C 49 H 31 N3=661.81)P-88m / z=611.24 (C 45 H 29 N3=611.75)P-89m / z=611.24 (C 45 H 29 N3=611.75)P-90m / z=585.22 (C 43 H 27 N3=585.71)P-91m / z=592.26(C 43 H 20 D7N3=592.75)P-92m / z=585.22 (C 43 H 27 N3=585.71)P-93m / z=635.24 (C 47 H 29 N3=635.77)P-94m / z=635.24 (C 47 H 29 N3=635.77)P-95m / z=635.24 (C 47 H 29 N3=635.77)P-96m / z=661.25 (C 49 H 31 N3=661.81)P-97m / z=661.25 (C 49 H 31 N3=661.81)P-98m / z=711.27 (C 53 H 33 N3=711.87)P-99m / z=711.27 (C 53 H 33 N3=711.87)P-100m / z=711.27 (C 53 H 33 N3=711.87)P-101m / z=711.27 (C 53 H 33 N3=711.87)P-102m / z=711.27 (C 53 H 33 N3=711.87)P-103m / z=711.27 (C 53 H 33N3=711.87)P-104m / z=711.27 (C 53 H 33 N3=711.87)P-105m / z=711.27 (C 53 H 33 N3=711.87)P-106m / z=711.27 (C 53 H 33 N3=711.87)P-107m / z=711.27 (C 53 H 33 N3=711.87)P-108m / z=761.28 (C 57 H 35 N3=761.93)P-109m / z=711.27 (C 53 H 33 N3=711.87)P-110m / z=711.27 (C 53 H 33 N3=711.87)P-111m / z=711.27 (C 53 H 33 N3=711.87)P-112m / z=585.22 (C 43 H 27 N3=585.71)P-113m / z=717.22 (C 51 H 31 N3S=717.89)P-114m / z=717.22 (C 51 H 31 N3S=717.89)P-115m / z=717.22 (C 51 H 31 N3S=717.89)P-116m / z=717.22 (C 51 H 31 N3S=717.89)P-117m / z=661.25 (C 49 H 31 N3=661.81)P-118m / z=711.27 (C 53 H 33 N3=711.87)P-119m / z=711.27 (C 53 H 33 N3=711.87)P-120m / z=711.27 (C 53 H 33 N3=711.87)P-121m / z=711.27 (C 53 H 33N3=711.87)P-122m / z=711.27 (C 53 H 33 N3=711.87)P-123m / z=711.27 (C 53 H 33 N3=711.87)P-124m / z=711.27 (C 53 H 33 N3=711.87)P-125m / z=701.25 (C 51 H 31 N3O=701.83)P-126m / z=717.22 (C 51 H 31 N3S=717.89)P-127m / z=701.25 (C 51 H 31 N3O=701.83)P-128m / z=717.22 (C 51 H 31 N3S=717.89)P-129m / z=611.24 (C 45 H 29 N3=611.75)P-130m / z=611.24 (C 45 H 29 N3=611.75)P-131m / z=661.25 (C 49 H 31 N3=661.81)P-132m / z=661.25 (C 49 H 31 N3=661.81)P-133m / z=701.25 (C 51 H 31 N3O=701.83)P-134m / z=687.27 (C 51 H 33 N3=687.85)P-135m / z=793.26 (C 57 H 35 N3S=793.99)P-136m / z=777.28 (C 57 H 35 N3O=777.93)

[0469] [합성예 2]

[0470] The compound represented by the above chemical formula 2 or the above chemical formula 3 can be manufactured by a known synthetic method (named reaction) or by referring to published patent publications, such as Korean Patent Registration No. 10-2395819 and U.S. Patent Publication No. 2023-0129535, but is not limited thereto.

[0471]

[0472] Meanwhile, although the above-described exemplary synthetic examples of the present invention represented by Chemical Formula 1 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.86-60 Org. Chem. 2005, 70, 5014), it will be easily understood by those skilled in the art that the above-described reaction proceeds even if a substituent other than the substituent specified in the specific synthetic example is combined.

[0473]

[0474] The FD-MS values ​​of compounds N-1 to N-96 and S-1 to S-108 of the present invention manufactured according to Synthesis Example 2 as described above are as shown in Tables 4 and 5 below.

[0475]

[0476] Compound FD-MS Compound FD-MSN-1 m / z = 487.19 (C 36 H 25 NO=487.60)N-2m / z=553.19(C 40 H 27 NS=553.72)N-3m / z=563.26(C 43H 33 N=563.74)N-4m / z=602.27(C 45 H 34 N2=602.78)N-5m / z=517.15(C 36 H 23 NOS=517.65)N-6m / z=603.20(C 44 H 29 NS=603.78)N-7m / z=735.29(C 57 H 37 N=735.93)N-8m / z=562.24(C 42 H 30 N2=562.72)N-9m / z=565.17(C 40 H 23 NO3=565.63)N-10m / z=581.14(C 40 H 23 NO2S=581.69)N-11m / z=823.24(C 59 H 37 NS2=824.07)N-12m / z=727.30(C 54 H 37 N3=727.91)N-13m / z=627.22(C 46 H 29 NO2=627.74)N-14m / z=633.16(C 44 H 27 NS2=633.83)N-15m / z=675.29(C 52 H 37 N=675.88)N-16m / z=678.30(C 51 H 38 N2=678.88)N-17m / z=669.21(C 48 H 31 NOS=669.84)N-18m / z=785.22(C 56 H 35 NS2=786.02)N-19m / z=617.18(C 44 H 27 NOS=617.77)N-20m / z=601.20(C 44 H 27 NO2=601.71)N-21m / z=779.32(C 59 H 41 NO=779.98)N-22m / z=583.23(C42 H 33 NS=583.79)N-23m / z=679.32(C 52 H 41 N=679.91)N-24m / z=726.27(C 54 H 34 N2O=726.88)N-25m / z=593.18(C 42 H 27 NOS=593.74)N-26m / z=774.22(C 54 H 34 N2S2=775.00)N-27m / z=557.24(C 40 H 31 NO2=557.69)N-28m / z=652.25(C 48 H 32 N2O=652.80)N-29m / z=619.29(C 46 H 37 NO=619.81)N-30m / z=603.20(C 44 H 29 NS=603.78)N-31m / z=813.30(C 62 H 39 NO=814.00)N-32m / z=784.29(C 57 H 40 N2S=785.02)N-33m / z=577.20(C 42 H 27 NO2=577.68)N-34m / z=607.14(C 42 H 25 NS2=607.79)N-35m / z=801.34(C 62 H 43 N=802.03)N-36m / z=575.24(C 42 H 29 N3=575.72)N-37m / z=577.20(C 42 H 27 NO2=577.68)N-38m / z=607.14(C 42 H 25 NS2=607.79)N-39m / z=801.34(C 62 H 43 N=802.03)N-40m / z=575.24(C 42 H 29N3=575.72)N-41m / z=601.20(C 44 H 27 NO2=601.71)N-42m / z=471.11(C 31 H 21 NS2=471.64)N-43m / z=675.29(C 52 H 37 N=675.88)N-44m / z=727.30(C 54 H 37 N3=727.91)N-45m / z=603.20(C 44 H 29 NS=603.78)N-46m / z=561.16(C 38 H 27 NS2=561.76)N-47m / z=799.32(C 62 H 41 N=800.02)N-48m / z=702.27(C 52 H 34 N2O=702.86)N-49m / z=729.27(C 54 H 35 NO2=729.88)N-50m / z=785.22(C 56 H 35 NS2=786.02)N-51m / z=812.32(C 62 H 40 N2=813.02)N-52m / z=681.22(C 48 H 31 N3S=681.86)N-53m / z=615.18(C 44 H 25 NO3=615.69)N-54m / z=763.15(C 52 H 29 NS3=763.99)N-55m / z=593.31(C 45 H 39 N=593.81)N-56m / z=840.33(C 62 H 40 N4=841.03)N-57m / z=657.18(C 46 H 27 NO2S=657.79)N-58m / z=824.23(C 58 H 36 N2S2=825.06)N-59m / z=1195.42(C91 H 57 NS=1196.52)N-60m / z=656.19(C 46 H 28 N2OS=656.80)N-61m / z=607.16(C 42 H 25 NO2S=607.73)N-62m / z=773.20(C 54 H 31 NO3S=773.91)N-63m / z=1013.40(C 79 H 51 (N=1014.28)N-64m / z=758.24(C 54 H 34 N2OS=758.94)N-65m / z=623.14(C 42 H 25 NOS2=623.79)N-66m / z=763.16(C 52 H 29 NO2S2=763.93)N-67m / z=799.20(C 56 H 33 NOS2=800.01)N-68m / z=743.23(C 54 H 33 NOS=743.92)N-69m / z=872.25(C 62 H 36 N2O2S=873.04)N-70m / z=772.22(C 54 H 32 N2O2S=772.92)N-71m / z=830.28(C 61 H 38 N2S=831.05)N-72m / z=808.25(C 58 H 33 FN2O2=808.91)N-73m / z=929.21(C 64 H 35 NO3S2=930.11)N-74m / z=963.27(C 68 H 41 N3S2=964.22)N-75m / z=809.24(C 58 H 35 NO2S=809.98)N-76m / z=893.29(C 66 H 39 NO3=894.04)N-77m / z=794.28(C 58H 38 N2S=795.02)N-78m / z=900.26(C 64 H 40 N2S2=901.16)N-79m / z=758.28(C 55 H 38 N2S=758.98)N-80m / z=1082.37(C 81 H 50 N2S=1083.37)N-81m / z=573.25(C 44 H 31 N=573.74)N-82m / z=649.28(C 50 H 35 N=649.84)N-83m / z=699.29(C 54 H 37 N=699.90)N-84m / z=699.29(C 54 H 37 N=699.90)N-85m / z=673.28(C 52 H 35 N=673.86)N-86m / z=649.28(C 50 H 35 N=649.84)N-87m / z=625.28(C 48 H 35 N=625.82)N-88m / z=673.28(C 52 H 35 N=673.86)N-89m / z=773.31(C 60 H 39 N=773.98)N-90m / z=749.31(C 58 H 39 N=749.96)N-91m / z=699.29(C 54 H 37 N=699.90)N-92m / z=599.26(C 46 H 33 N=599.78)N-93m / z=639.26(C 48 H 33 NO=639.80)N-94m / z=765.25(C 57 H 35 NS=765.97)N-95m / z=677.31(C 52 H 39 N=677.89)N-96m / z=727.30(C 54H 37 N3=727.91)N-97m / z=552.18(C 39 H 24 N2O2=552.63)N-98m / z=628.22(C 45 H 28 N2O2=628.73)N-99m / z=614.24(C 45 H 30 N2O=614.75)N-100m / z=614.24(C 45 H 30 N2O=614.75)N-101m / z=691.21(C 50 H 29 NO3=691.79)N-102m / z=739.29(C 56 H 37 NO=739.92)N-103m / z=673.15(C 46 H 27 NOS2=673.85)N-104m / z=726.27(C 54 H 34 N2O=726.88)N-105m / z=667.2(C 48 H 29 NOS=667.83)N-106m / z=717.21(C 52 H 31 NOS=717.89)N-107m / z=667.2(C 48 H 29 NOS=667.83)N-108m / z=711.26(C 54 H 33 NO=711.86)N-109m / z=617.18(C 44 H 27 NOS=617.77)N-110m / z=611.22(C 46 H 29 NO=611.74)N-111m / z=769.24(C 56 H 35 NOS=769.96)N-112m / z=701.28(C 52 H 35 N3=701.87)N-113m / z=527.22(C 39 H 29 NO=527.67)N-114m / z=643.2(C 46 H 29NOS=643.8)N-115m / z=593.18(C 42 H 27 NOS=593.74)N-116m / z=726.27(C 54 H 34 N2O=726.88)N-117m / z=726.27(C 54 H 34 N2O=726.88)N-118m / z=558.14(C 37 H 22 N2O2S=558.66)N-119m / z=620.19(C 43 H 28 N2OS=620.77)N-120m / z=610.24(C 46 H 30 N2=610.76)N-121m / z=718.24(C 52 H 34 N2S=718.92)N-122m / z=728.28(C 54 H 36 N2O=728.9)N-123m / z=592.2(C 42 H 28 N2S=592.76)N-124m / z=756.22(C 54 H 32 N2OS=756.92)N-125m / z=547.23(C 42 H 29 N=547.7)N-126m / z=672.28(C 49 H 24 D7NO2=672.83)N-127m / z=626.28(C 48 H 26 D5N=626.81)N-128m / z=558.22(C 40 H 22 D5NS=558.75)

[0477] 화합물FD-MS화합물FD-MSS-1m / z=408.16(C 30 H 20 N2=408.50)S-2m / z=534.21(C 40 H 26 N2=534.66)S-3m / z=560.23(C 42 H 28 N2=560.70)S-4m / z=584.23(C44 H 28 N2=584.72)S-5m / z=560.23(C 42 H 28 N2=560.70)S-6m / z=634.24(C 48 H 30 N2=634.78)S-7m / z=610.24(C 46 H 30 N2=610.76)S-8m / z=498.17(C 36 H 22 N2O=498.59)S-9m / z=574.20(C 42 H 26 N2O=574.68)S-10m / z=660.26(C 50 H 32 N2=660.82)S-11m / z=686.27(C 52 H 34 N2=686.86)S-12m / z=620.14(C 42 H 24 N2S2=620.79)S-13m / z=640.20(C 46 H 28 N2S=640.80)S-14m / z=560.23(C 42 H 28 N2=560.70)S-15m / z=558.21(C 42 H 26 N2=558.68)S-16m / z=548.19(C 40 H 24 N2O=548.65)S-17m / z=573.22(C 42 H 27 N3=573.70)S-18m / z=564.17(C 40 H 24 N2S=564.71)S-19m / z=574.20(C 42 H 26 N2O=574.68)S-20m / z=564.17(C 40 H 24 N2S=564.71)S-21m / z=564.17(C 40 H 24 N2S=564.71)S-22m / z=813.31(C 61 H 39N3=814.00)S-23m / z=696.26(C 53 H 32 N2=696.85)S-24m / z=691.23(C 49 H 29 N3O2=691.79)S-25m / z=710.27(C 54 H 34 N2=710.88)S-26m / z=610.24(C 46 H 30 N2=610.76)S-27m / z=670.15(C 46 H 26 N2S2=670.85)S-28m / z=640.29(C 48 H 36 N2=640.83)S-29m / z=598.20(C 44 H 26 N2O=598.71)S-30m / z=623.24(C 46 H 29 N3=623.76)S-31m / z=458.18(C 34 H 22 N2=458.56)S-32m / z=548.19(C 40 H 24 N2O=548.65)S-33m / z=508.19(C 38 H 24 N2=508.62)S-34m / z=508.19(C 38 H 24 N2=508.62)S-35m / z=623.24(C 46 H 29 N3=623.76)S-36m / z=564.17(C 40 H 24 N2S=564.71)S-37m / z=627.20(C 46 H 29 NS=627.81)S-38m / z=505.10(C 34 H 19 NS2=505.65)S-39m / z=514.15(C 36 H 22 N2S=514.65)S-40m / z=575.17(C 42 H 25 NS=575.73)S-41m / z=642.21(C 46H 30 N2S=642.82)S-42m / z=575.17(C 42 H 25 NS=575.73)S-43m / z=606.18(C 42 H 26 N2OS=606.74)S-44m / z=575.17(C 42 H 25 NS=575.73)S-45m / z=551.17(C 40 H 25 NS=551.71)S-46m / z=607.14(C 42 H 25 NS2=607.79)S-47m / z=525.16(C 38 H 23 NS=525.67)S-48m / z=642.21(C 46 H 30 N2S=642.82)S-49m / z=548.19(C 40 H 24 N2O=548.65)S-50m / z=473.14(C 34 H 19 NO2=473.53)S-51m / z=566.15(C 39 H 22 N2OS=566.68)S-52m / z=459.16(C 34 H 21 NO=459.55)S-53m / z=473.14(C 34 H 19 NO2=473.53)S-54m / z=523.16(C 38 H 21 NO2=523.59)S-55m / z=539.13(C 38 H 21 NOS=539.65)S-56m / z=548.19(C 40 H 24 N2O=548.65)S-57m / z=489.12(C 34 H 19 NOS=489.59)S-58m / z=545.09(C 36 H 19 NOS2=545.67)S-59m / z=549.17(C 40 H 23NO2=549.63)S-60m / z=565.15(C 40 H 23 NOS=565.69)S-61m / z=523.16(C 38 H 21 NO2=523.59)S-62m / z=598.20(C 44 H 26 N2O=598.71)S-63m / z=539.13(C 38 H 21 NOS=539.65)S-64m / z=589.15(C 42 H 23 NOS=589.71)S-65m / z=498.17(C 36 H 22 N2O=498.59)S-66m / z=509.18(C 38 H 23 NO=509.61)S-67m / z=548.19(C 40 H 24 N2O=548.65)S-68m / z=549.17(C 40 H 23 NO2=549.63)S-69m / z=449.12(C 32 H 19 NS=449.57)S-70m / z=439.10(C 30 H 17 NOS=439.53)S-71m / z=647.22(C 49 H 29 NO=647.78)S-72m / z=717.28(C 52 H 35 N3O=717.87)S-73m / z=459.16(C 34 H 21 NO=459.55)S-74m / z=533.18(C 40 H 23 NO=533.63)S-75m / z=525.16(C 38 H 23 NS=525.67)S-76m / z=564.17(C 40 H 24 N2S=564.71)S-77m / z=575.19(C 42 H 25 NO2=575.67)S-78m / z=663.22(C49 H 29 NO2=663.78)S-79m / z=647.22(C 49 H 29 NO=647.78)S-80m / z=496.16(C 36 H 20 N2O=496.57)S-81m / z=565.15(C 40 H 23 NOS=565.69)S-82m / z=505.10(C 34 H 19 NS2=505.65)S-83m / z=765.25(C 56 H 35 NOSi=765.99)S-84m / z=615.17(C 44 H 25 NOS=615.75)S-85m / z=603.17(C 43 H 25 NOS=603.74)S-86m / z=772.29(C 59 H 36 N2=772.95)S-87m / z=802.33(C 61 H 42 N2=803.02)S-88m / z=607.23(C 47 H 29 N=607.76)S-89m / z=524.23(C 39 H 28 N2=524.67)S-90m / z=665.22(C 49 H 31 NS=665.85)S-91m / z=633.25(C 49 H 31 N=633.79)S-92m / z=775.29(C 59 H 37 NO=775.95)S-93m / z=535.23(C 41 H 29 N=535.69)S-94m / z=623.22(C 47 H 29 NO=623.76)S-95m / z=687.20(C 51 H 29 NS=687.86)S-96m / z=735.29(C 57 H 37N=735.93)S-97m / z=611.26(C 47 H 33 N=611.79)S-98m / z=679.23(C 50 H 33 NS=679.88)S-99m / z=787.32(C 61 H 41 N=788.01)S-100m / z=743.33(C 55 H 41 N3=743.95)S-101m / z=485.21(C 37 H 27 N=485.63)S-102m / z=471.20(C 36 H 25 N=471.60)S-103m / z=571.19(C 43 H 25 NO=571.68)S-104m / z=584.23(C 44 H 28 N2=584.72)S-105m / z=539.24(C 40 H 21 D5N2=539.69)S-106m / z=453.15(C 32 H 15 NS=471.60)S-107m / z=563.26(C 43 H 26 D4NO=563.74)S-108m / z=589.26(C 44 H 23 D5N2=584.72)S-109m / z=589.26(C 44 H 23 D5N2=589.75)S-110m / z=624.22(C 46 H 28 N2O=624.74)S-111m / z=589.26(C 44 H 23 D5N2=589.75)S-112m / z=634.24(C 48 H 30 N2=634.78)S-113m / z=589.26(C 44 H 23 D5N2=589.75)S-114m / z=562.23(C 42 H 22D4N2=562.71)S-115m / z=660.26(C 50 H 32 N2=660.82)S-116m / z=553.22(C 40 H 19 D5N2O=553.68)S-117m / z=634.24(C 48 H 30 N2=634.78)S-118m / z=589.26(C 44 H 23 D5N2=589.75)S-119m / z=588.25(C 44 H 24 D4N2=588.75)S-120m / z=513.23(C 38 H 19 D5N2=513.65)

[0478] [Example 1] Red organic electroluminescent device (phosphorescent host)

[0479] Compound A and Compound B were used on the ITO layer (anode) formed on a glass substrate, and Compound B was doped at a weight ratio of 98:2 to form a hole injection layer with a thickness of 10 nm. Then, Compound A was vacuum-deposited on the hole injection layer with a thickness of 110 nm to form a hole transport layer.

[0480] Next, a compound CR was vacuum-deposited to a thickness of 10 nm on the hole transport layer to form a light-emitting auxiliary layer. Thereafter, the host material of the light-emitting layer used compound P-1, a compound of the present invention, as a first host, and compound N-17, a compound of the present invention, as a second host, a mixture in which the first host and the second host were mixed at a weight ratio of 5:5, and bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate (hereinafter abbreviated as '(piq)2Ir(acac)') was used as a dopant material, and the dopant was doped so that the weight ratio of the host and the dopant was 95:5, thereby forming a light-emitting layer with a thickness of 30 nm.

[0481] Next, compound E was vacuum-deposited on the light-emitting layer to form a hole-blocking layer with a thickness of 10 nm, and a mixture of compound F and compound G at a weight ratio of 5:5 was used to form an electron-transporting layer with a thickness of 30 nm on the hole-blocking layer. Thereafter, compound G was deposited on the electron-transporting layer to form an electron-injection layer with a thickness of 0.2 nm, and then Al was deposited to form a cathode with a thickness of 150 nm.

[0482]

[0483] Compound A: N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0484] Compound B: 4,4',4''-((1E,1'E,1''E)-cyclopropane-1,2,3-triylidenetris(cyanomethaneylylidene))tris(2,3,5,6-tetrafluorobenzonitrile)

[0485] Compound CR:N 7 -(dibenzo[b,d]thiophen-2-yl)-N 2 ,N 2 ,N 7 -triphenyldibenzo[b,d]thiophene-2,7-diamine

[0486] Compound E: 2-(4'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine

[0487] Compound F: 2,7-bis(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalene

[0488] Compound G: (8-quinolinolato)lithium

[0489]

[0490] [Example 2] to [Example 36]

[0491] An organic light-emitting device was manufactured in the same manner as Example 1, except that the compounds described in Table 6 below were used as the first host and second host of the light-emitting layer.

[0492]

[0493] [Comparative Example 1] to [Comparative Example 4]

[0494] An organic light-emitting device was manufactured in the same manner as in Example 1, except that Comparative Compounds A to D were used as the first host material of the light-emitting layer.

[0495]

[0496] Comparative Compound A Comparative Compound B Comparative Compound C

[0497]

[0498] Comparative Compound D

[0499]

[0500] The organic electroluminescence devices manufactured by the examples and comparative examples were subjected to a forward bias DC voltage and the electroluminescence (EL) characteristics were measured using a PR-650 from Photoresearch. The measurement result was 2500 cd / m 2 The T95 lifespan was measured using a lifespan measuring device manufactured by Maxscience at a reference luminance. Table 6 below shows the results of the device fabrication and evaluation.

[0501]

[0502] These measuring devices are not affected by daily variations in deposition rate, vacuum quality or other parameters and allow new performance to be evaluated by comparison with reference compounds under identical conditions.

[0503] 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 have statistical significance.

[0504]

[0505] Compound 1 Compound 2 Driving voltage (V) Current (mA / cm) 2) Efficiency (cd / A) T (95) Comparative Example 1 Comparative Compound AN-175.5 11.4 21.9 95.2 Comparative Example 2 Comparative Compound BN-175.8 12.3 20.4 91.4 Comparative Example 3 Comparative Compound CN-175.6 11.8 21.2 93.0 Comparative Example 4 Comparative Compound DN-175.4 10.62 3.5101.6Embodiment 1P-1N-174.25.545.2141.0Embodiment 2P-2N-174.25.644.8144.1Embodiment 3P-3N-174.25.843.0140.3Embodiment 4P-8N-174.55.942.4139.4Embodiment 5P-17N-17 4.55.942.1138.7 Example 6P-22N-174.36.041.9138.1 Example 7P-27N-174.55.842.8139.7 Example 8P-38N-174.25.644.9143.9 Example 9P-41N-174.25.644.5144.5 Example 10P-54N-174.76.637.9129.1 Example 11P-61N-174.76.836.5127.7 Example 12P-69N-174.87.135.2125.4 Example 13P-70N-174.87.035.7126.6 Example 14P-76N-17 4.76.936.2127.2Example 15P-91N-174.36.041.8143.2Example 16P-111N-174.46.141.1136.9Example 17P-112N-174.36.240.6136.8Example 18P-118N-174.46.340. 0135.2 Example 19P-125N-174.66.538.7127.4 Example 20P-130N-174.66.339.6133.3 Example 21P-131N-174.56.538.3127.5 Example 22P-1N-1094.35.842.9138.6 Example 23P-8N-1094.56.240.1137.1 Example 24P-22N-1094.36.339.5135.7 Example 25P-118N-1094.46.637.8132.9 Example 26P-130N-1094.66.737.1130.7 Example 27P-1S- 34.15.843.4139.1Embodiment 28P-8S-34.46.240.5137.7Embodiment 29P-22S-34.26.240.2136.3Embodiment 30P-118S-34.36.538.2133.6Embodiment 31P-130S-34.56.637.6131.2Example 32P-1S-1104.15.843.3139.8Example 33P-8S-1104.46.240.5138.0Example 34P-22S-1104.26.240.1136.8Example 35P-118S-1104.36.638.0133.7Example 36P-130S-1104.56.737.5131.5.

[0506] As can be seen from the results in Table 6 above, when a red organic light-emitting device was manufactured using the compound of the present invention as a phosphorescent host material, not only was the driving voltage of the organic light-emitting device lowered compared to when comparative compounds A to D were used, but the efficiency and lifespan were also significantly improved.

[0507] As can be seen above, when a host for a light-emitting layer is formed by mixing multiple compounds, the characteristics differ depending on the type of the first and second compounds. In addition, when the same compound is applied to the second compound, it can be confirmed that there is a significant difference in characteristics depending on the type of the first compound. Similarly, the second compound shows differences in driving voltage, efficiency, and lifespan depending on the type.

[0508] Comparative compounds A to D have a similar skeleton to the compound of the present invention, but differ in the substitution position and type of substituent.

[0509]

[0510]

[0511] The compound of the present invention is characterized in that a triazine moiety is substituted at the 3-position of phenanthrene, and an additional substituent is positioned at the 9-position. On the other hand, comparative compounds A to C are different in that triazine and secondary substituents are positioned at the 2-position and 10-position of phenanthrene, the 3-position and 10-position of phenanthrene, and the 3-position and 5-position of phenanthrene, respectively. In addition, comparative compound C is different from the compound of the present invention in that a phenyl group is additionally substituted on the naphthyl group substituted on the triazine. Finally, comparative compound D is different in that phenanthrene is introduced at the 9-position of phenanthrene, and a naphthyl group is not positioned on the triazine.

[0512] In order to determine the difference in energy levels of compounds according to the structural differences of these compounds, the energy levels of comparative compounds A to D and similar compounds P-3, P-34, and P-76 of the present invention were measured using the DFT method (B3LYP / 6-31g(D)) of the Gaussian program. The measurement results are shown in Table 7 below.

[0513]

[0514] Compound LUMO (eV)P-3-1.972Comparative compound A-1.899Comparative compound D-1.966

[0515] Compound LUMO (eV) P-27 -1.954 Comparative compound C -1.936

[0516] Compound LUMO (eV) P-76-2.005 Comparative compound B-1.998

[0517] Referring to Tables 7 to 9 above, it can be seen that the compounds of the present invention have lower LUMO energy levels than the comparative compounds. In the case of the compounds of the present invention, they participate in electron transport within the light-emitting layer as the first host compound, and play a role in accepting and moving electrons entering from the electron transport layer to the light-emitting layer. It can be seen that the compounds of the present invention having lower LUMO energy levels than the comparative compounds mean that the electronic properties of the compounds are relatively high. Accordingly, electrons can be injected more easily from the electron transport layer to the light-emitting layer, and electrons can be moved more effectively within the light-emitting layer.

[0518] When a light-emitting layer is composed of multiple host compounds, the characteristics are different depending on the types of the first and second compounds, and it is judged that the driving, efficiency and lifetime are determined depending on the degree of ease of injection and movement of holes and electrons. Therefore, when the compound of the present invention is used in the light-emitting layer, it can be expected that as the electron mobility of the electron-transporting host improves, the light-emitting region moves toward the interface between the hole transport layer and the light-emitting layer, and the degree of accumulation of holes flowing into the light-emitting layer from the hole transport layer is reduced. In other words, it appears that the efficiency and lifetime are improved because the charge balance of electrons and holes is well achieved within the light-emitting layer.

[0519] From the above Tables 6 to 9, it can be confirmed that the compound of the present invention, which satisfies all complex factors such as the type of substituent and the substitution position of the substituent, even though it is a compound having a similar configuration, exhibits a remarkable effect in an organic electric device compared to other comparative compounds, and through this, it can be seen that the compound of the present invention, which satisfies all specific configurations, exhibits a remarkable effect in an organic electric device compared to other comparative compounds not described in the present specification.

[0520] These results suggest that even if the molecular components are similar, the properties of the compound, such as hole characteristics, light efficiency characteristics, energy levels, hole injection and mobility characteristics, charge balance of holes and electrons, volume density, and intermolecular distance, can differ significantly to an extent that is difficult to predict depending on the type and position of the substituted substituent, and that the performance of the device can vary not only due to a single component but also due to complex factors, rather than affecting the results of the entire device.

[0521] The above description is merely illustrative of the present invention. Those skilled in the art will appreciate that various modifications may be made without departing from the essential characteristics of the present invention. The scope of protection of the present invention should be construed in accordance with the claims below, and all techniques within the scope equivalent thereto should be construed as being included within the scope of the present invention.

[0522] 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 {In the above chemical formula 1, 1) R 1 and R 2 are each the same or different from each other, and are independently hydrogen; or deuterium; and a plurality of R 1 Kiri or R 2 They cannot combine with each other to form rings, a is an integer from 0 to 8, b is an integer from 0 to 7, 2) Ar1 is substituted or unsubstituted C6~C 24 Aryl group of; or C2~C containing at least one heteroatom among substituted or unsubstituted O, N, S, Si and P 60 A heterocyclic group; wherein the substituted aryl group and the substituted heterocyclic group are each independently hydrogen; deuterium; C6~C 20 Aryl group of; or C6~C substituted with deuterium 20 is substituted with an aryl group; 3) Ar2 is substituted or unsubstituted C6~C 12 Aryl group; and, 4) L1 and L2 are each the same or different and independently a single bond; substituted or unsubstituted C6~C 60 Arylene group of; or C2~C containing at least one heteroatom among substituted or unsubstituted O, N, S, Si and P 60 is a heterocyclic group; and Here, in the case where Ar2, L1 and L2 are substituted aryl groups, substituted arylene groups and substituted heterocyclic groups, the substituents are each independently hydrogen; or deuterium; 2. In paragraph 1, the chemical formula 1 is a compound represented by the following chemical formula 1-1 or chemical formula 1-2. Chemical Formula 1-1 Chemical Formula 1-2 {In the above chemical formulas 1-1 and 1-2, R 1 , R 2 , Ar1, Ar2, L1, L2, a and b are the same as defined in claim 1.

3. In the first paragraph, the compound is characterized in that the Ar1 is selected from any one of the following chemical formulas Ar-1 to Ar-17. Ar-1 Ar-2 Ar-3 Ar-4 Ar-5 Ar-6 Ar-7 Ar-8 Ar-9 Ar-10 Ar-11 Ar-12 Ar-13 Ar-14 Ar-15 Ar-16 Ar-17 {In the above chemical formulas Ar-1 to Ar-17, R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are identical or different from each other, and independently of each other, hydrogen; deuterium; C6~C 20 Aryl group of; or C6~C substituted with deuterium 20 aryl group of; and, c is an integer from 0 to 5, d, f and g are integers from 0 to 7, e is integers from 0 to 9, h is integers from 0 to 8, * indicates the position where it binds to L1.

4. In the first paragraph, a compound characterized in that Ar2 is selected from any one of the following chemical formulas Ar2-1 to Ar2-6. Ar2-1 Ar2-2 Ar2-3 Ar2-4 Ar2-5 Ar2-6 {In the above chemical formulas Ar2-1 to Ar2-6, R 9 , R 10 , R 11 and R 12 are identical or different from each other and are independently hydrogen; or deuterium; i is an integer from 0 to 5, j is an integer from 0 to 7, k is an integer from 0 to 4, l is an integer from 0 to 5, * indicates the position where Ar2 is bonded in chemical formula 1.

5. In the first paragraph, a compound characterized in that L1 and L2 are selected from any one of the following chemical formulas L-1 to L-10. L-1 L-2 L-3 L-4 L-5 L-6 L-7 L-8 {In the above chemical formulas L-1 to L-8, R 13 , R 14 , R 15 , R 16 and R 17 are identical or different from each other and are independently hydrogen; or deuterium; m is an integer from 0 to 4, n, o and p are any integer from 0 to 6, q is an integer between 0 and 7, * indicates the positions where L1 and L2 are bonded in chemical formula 1.

6. In the first paragraph, the compound represented by the chemical formula 1 is a compound characterized in that at least one deuterium is substituted.

7. In the first paragraph, the compound characterized in that the chemical formula 1 is selected from any one of the following chemical formulas P-1 to P-136.

8. A composition for an organic electric device comprising the compound of paragraph 1; and a compound represented by the following chemical formula 2 or chemical formula 3; <Chemical Formula 2> <Chemical Formula 3> {In the above chemical formula 2 and chemical formula 3, L 11 , L 12 , L 13 and L 14 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; Ar 11 , Ar 12 and Ar 13 are independently C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C3~C 60 Aliphatic ring group; 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; Ar 14 is C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 A fused ring group of an aromatic ring; and -L'-NR'R"; is selected from the group consisting of, Z is O, S, CR 51 R 52 or NR 53 And, Ring A is C6~C 20 is an aryl group, L' is a single bond; C6~C 60 Arylene group; Fluorenylene group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; and C3~C 60 is selected from the group consisting of aliphatic rings; R 51 , R 52 , R 53 , R' and R" are the above Ar 11 is identical to the definition of , or R 51 and R 52 can combine with each other to form spy rings, R 21 and R 22 are identical or different from each other, and independently of each other, hydrogen; deuterium; halogen; cyano group; C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C1~C 50 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 An aryloxy group of R is selected from the group consisting of, or a plurality of adjacent R 21 R's or multiple R's 22 They can combine with each other to form rings, aa and ab are integers from 0 to 4, independently of each other, Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 Alkylthio group of; C1~C 20 Alkoxyl group of; 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 Cycloalkyl group of; C7~C 20 Arylalkyl group of; C8~C 20 Aryl alkenyl group of; and -L'-NR'R"; may be further substituted with one or more substituents selected from the group consisting of, and further, the hydrogen of these substituents may be further substituted with one or more deuteriums, and further, these substituents may be combined with each other to form a ring, wherein the 'ring' refers to a group consisting of 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.

9. In the 8th paragraph, the composition for an organic electric device is characterized in that it is a host for a light-emitting layer.

10. In an organic electric device comprising a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode; An organic electric device characterized in that the organic material layer comprises a compound represented by the chemical formula 1 of claim 1 or a composition for an organic electric device of claim 8.

11. An organic electric device characterized in that it further includes a light efficiency improvement layer formed on at least one surface of the first electrode and the second electrode, which is opposite to the organic layer, in the 10th paragraph.

12. An organic electric device according to claim 10, 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.

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

14. 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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