Compound for organic electronic element, organic electronic element using compound, and electronic device thereof

Abstract

Provided are a novel compound which can improve the luminous efficiency, stability, and lifespan of an element, and an organic electronic element and an electronic device using the same.

Description

[0001] Cross - reference to related applications

[0002] This application claims the priority and benefits of Korean Patent Applications 10 - 2023 - 0172026 and 10 - 2023 - 0172303, filed with the Korean Intellectual Property Office on December 1, 2023, the entire contents of which are incorporated herein by reference. Technical field

[0003] The present invention relates to a compound for an organic electronic element, an organic electronic element using the compound, and an electronic device thereof. Background art

[0004] Generally, the organic light - emitting phenomenon refers to the phenomenon of converting electrical energy into light energy by using organic materials. An organic electronic element using the organic light - emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer disposed therebetween. Here, in order to increase the efficiency and stability of the organic electronic element, the organic material layer is usually composed of a multilayer structure made of different materials, and may include, for example, a hole injection layer, a hole transport layer, a light - emitting layer, an electron transport layer, an electron injection layer, etc.

[0005] The materials used as the organic material layer in an organic electronic element can be classified into light - emitting materials and charge - transport materials according to their functions, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc. Moreover, light - emitting materials can be classified into high - molecular - type and low - molecular - type according to 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 according to the light - emitting mechanism. In addition, light - emitting materials can be classified into blue light - emitting materials, green light - emitting materials, and red light - emitting materials, as well as yellow light - emitting materials and orange light - emitting materials required to achieve better natural colors.

[0006] However, when only one substance is used as the light - emitting material, due to molecular interaction, the maximum emission wavelength shifts to a longer wavelength, resulting in a decrease in color purity, or due to the light - emitting decay effect, the device efficiency decreases. Therefore, a host / dopant system can be used as the light - emitting material to improve color purity and light - emitting efficiency through energy transfer. The principle is that when a small amount of a dopant having a smaller band gap than that of the host forming the light - emitting layer is mixed in the light - emitting layer, excitons generated in the light - emitting layer are transferred to the dopant to emit light efficiently. Here, since the wavelength of the host shifts to the wavelength band of the dopant, light with a desired wavelength can be obtained according to the type of dopant used.

[0007] Currently, the portable display market is large-area displays, and their size is increasing day by day, and therefore, more power consumption than that required by existing portable displays is required. Therefore, for portable displays with limited power supply such as batteries, power consumption becomes a very important factor, and the issues of efficiency and service life must also be solved.

[0008] Efficiency, service life and driving voltage are related. As efficiency increases, the driving voltage decreases relatively. As the driving voltage decreases, due to the Joule heating generated during operation, the crystallization of organic substances decreases, resulting in an increase in service life. However, efficiency cannot be maximized simply by improving the organic material layer. This is because long service life and high efficiency can only be achieved simultaneously when the energy levels and T1 values ​​between the organic material layers and the inherent properties of the materials (mobility, interface properties, etc.) are optimally combined.

[0009] Therefore, it is necessary to delay the penetration and diffusion of metal oxide from the anode electrode (ITO) into the organic layer, which is one of the reasons for the shortened service life of organic electronic components, and to have stable characteristics against Joule heating generated when operating the components. In addition, since OLED devices are mainly formed by a deposition method, it is necessary to develop a material that can withstand a long deposition process, that is, a material with strong heat resistance.

[0010] That is, in order to fully demonstrate the excellent characteristics of organic electronic components, priority should be given to materials that are stable and effective as the materials constituting the organic material layer in the component, such as hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, etc. However, the development of stable and effective organic material layer materials for organic electronic components has not been fully realized. Therefore, it is necessary to continuously develop new materials, and in particular, it is urgent to develop host materials for the luminescent layer. Summary of the invention

[0011] In order to solve the above-mentioned problems of the background art, the present invention has discovered a compound having a new structure, and also discovered that when the compound is applied to an organic electronic element, the luminous efficiency, stability and service life of the element can be greatly improved.

[0012] Therefore, an object of the present invention is to provide a novel compound, an organic electronic element using the compound, and an electronic device thereof.

[0013] [Technical solution]

[0014] The present invention provides a composition for an organic electronic device, the composition comprising a mixture of a compound represented by Formula 1 and a compound represented by Formula 5.

[0015] Formula 1

[0016]

[0017] Formula 5

[0018]

[0019] In addition, on the other hand, the present invention provides an organic electronic element and an electronic device thereof, and the organic electronic element includes a composition for an organic electronic element or a compound represented by Formula 1.

[0020] [Advantages of the Invention]

[0021] By using the compound according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the element can be achieved, and the color purity and service life of the element can be greatly improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] Figures 1 to 3 is an exemplary view of an organic electroluminescent device according to the present invention.

[0023] Figure 4 shows a formula according to an aspect of the present invention.

[0024] Figure 5 shows the composition of the compound represented by Formula 1 of the present invention.

[0025] Figure 6 is a LUMO electron cloud image of Compound P-1 of the present invention.

[0026] Figure 7 is the IR spectral data of Compound P-1 of the present invention.

[0027] Figure 8 shows the IR spectral data of Comparative Compound D.

[0028] Figure 9 is the IR spectral data of Compound P-21 of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0029] Hereinafter, some embodiments of the present invention will be described in detail. In addition, in the following description of the present invention, when the detailed description of known functions and configurations incorporated herein may make the subject matter of the present invention rather unclear, the detailed description will be omitted.

[0030] In addition, when describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used herein. Each of these terms is not used to define the essence, order or sequence of the corresponding components, but is only used to distinguish the corresponding components from other components. It should be noted that if a component is described as "connected", "coupled" or "joined" to another component, the component may be directly connected or joined to the other component, but another component may be "connected", "coupled" or "joined" between the components.

[0031] As used in the specification and the appended claims, unless otherwise specified, the following are the meanings of the following terms.

[0032] Unless otherwise specified, the term "halo" or "halogen" as used herein includes fluorine, bromine, chlorine or iodine.

[0033] Unless otherwise specified, the term "alkyl" or "alkyl group" as used herein has a single bond with 1 to 60 carbon atoms and means a saturated aliphatic functional group, including straight-chain alkyl groups, branched-chain alkyl groups, cycloalkyl groups (alicyclic), cycloalkyl groups substituted with alkyl groups or alkyl groups substituted with cycloalkyl groups.

[0034] Unless otherwise specified, the term "alkenyl" or "alkynyl" as used herein has a double bond or triple bond with 2 to 60 carbon atoms, but is not limited thereto, and includes straight-chain or branched-chain groups.

[0035] Unless otherwise specified, the term "cycloalkyl" as used herein means an alkyl group forming a ring with 3 to 60 carbon atoms, but is not limited thereto.

[0036] Unless otherwise specified, the term "alkoxy group", "alkoxy" or "alkyloxy group" as used herein means an oxy group connected to an alkyl group, but is not limited thereto, and has 1 to 60 carbon atoms.

[0037] Unless otherwise specified, the term "aryloxy group" or "aryloxyl group" as used herein means an oxy group connected to an aryl group, but is not limited thereto, and has 6 to 60 carbon atoms.

[0038] Unless otherwise specified, the term "aryl group" or "arylene group" as used herein has 6 to 60 carbon atoms, but is not limited thereto. As used herein, an aryl group or arylene group means a monocyclic and polycyclic aromatic group, and includes aromatic rings formed by adjacent substituents participating in bonding or reaction. Examples of "aryl group" may include phenyl group, biphenyl group, fluorene group or spirofluorene group.

[0039] The prefix "aryl" or "ar" means a group substituted with an aryl group. For example, arylalkyl can be an alkyl group substituted with an aryl group, and arylalkenyl can be an alkenyl group substituted with an aryl group, and the group substituted with an aryl group has the number of carbon atoms as defined herein.

[0040] In addition, when the prefixes are named in sequence, this means listing the substituents in the order described first. For example, arylalkoxy means an alkoxy group substituted with an aryl group, alkoxycarbonyl means a carbonyl group substituted with an alkoxy group, and arylcarbonylalkenyl also means an alkenyl group substituted with an arylcarbonyl group, where arylcarbonyl can be a carbonyl group substituted with an aryl group.

[0041] Unless otherwise specified, the term "heterocyclic group" as used herein contains one or more heteroatoms, but is not limited thereto, has 2 to 60 carbon atoms, includes either monocyclic or polycyclic rings, and can include heteroaliphatic rings and / or heteroaromatic rings. In addition, it can also form a heterocyclic group together with adjacent groups.

[0042] Unless otherwise specified, the term "heteroatom" as used herein represents at least one of N, O, S, P, or Si.

[0043] In addition, the term "heterocyclic group" can include rings containing SO 2 instead of a ring-forming carbon. For example, the "heterocyclic group" includes the following compounds.

[0044]

[0045] Unless otherwise specified, the term "fluorenyl group" or "fluorenylene group" as used herein means a monovalent or divalent functional group in which R, R', and R'' are all hydrogen in the following structure, and the term "substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', R'' is a substituent other than hydrogen, and includes those in which R and R' are bonded to each other to form a spiro compound together with the carbon to which they are bonded.

[0046]

[0047] The term "spiro compound" as used herein has "spiro linkage", and spiro linkage means a connection in which two rings share only one atom. Among them, the atom shared in the two rings is called a "spiro atom", and these compounds are respectively called "monospiro-", "dispiro-", and "trispiro-" according to the number of atoms in the compound.

[0048] Unless otherwise specified, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the term "aliphatic ring" as used herein means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

[0049] Unless otherwise specified, as used herein, the term "ring" means an aliphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6 to 60 carbon atoms, or a heterocyclic ring having 2 to 60 carbon atoms, or a fused ring formed by their combination, and includes a saturated ring or an unsaturated ring.

[0050] In addition to the above-mentioned hetero compounds, other hetero compounds or hetero groups contain one or more heteroatoms, but are not limited thereto.

[0051] Unless otherwise specified, as used herein, the term "substituted or unsubstituted" means that the substitution is substituted by at least one substituent selected from deuterium, halogen, amino group, nitrile group, nitro group, C 1 -C 20 alkyl group, C 1 -C 20 alkoxy group, C 1 -C 20 alkylamine group, C 1 -C 20 alkylthiophene group, C 6 -C 20 arylthiophene group, C 2 -C 20 alkenyl group, C 2 -C 20 alkynyl group, C 3 -C 20 cycloalkyl group, C 6 -C 20 aryl group, deuterium-substituted C 6 -C 20 aryl group, C 8 -C 20 arylalkenyl group, silyl group, boron group, germanium group and C 2 -C 20 heterocyclic group, but not limited thereto.

[0052] Unless otherwise explicitly specified, as used herein, the formulas used in the present invention are applied in the same manner as the definition of substituents according to the exponents of the following formulas.

[0053]

[0054] Wherein, when a is an integer of 0, the substituent R 1 does not exist, when a is an integer of 1, the only substituent R 1 is connected to any one of the carbons constituting the benzene ring, when a is an integer of 2 or 3, each substituent R 1May be the same or different, and when a is an integer from 4 to 6, it is connected to the benzene ring in a similar manner, but the indication of the hydrogen bonded to the carbon forming the benzene ring is omitted.

[0055]

[0056] As used herein, the term "composition" is intended to be construed broadly and includes compounds as well as solutions, dispersions, liquid and solid mixtures (mixtures, admixtures). The compositions of the present invention may comprise the compounds of the present invention alone, or may comprise compounds in combinations of two or more different types, or may comprise compounds in combinations of two or more types with other compounds. In other words, the composition may include only the compounds corresponding to Formula 1, a mixture of two or more compounds of Formula 1, or a mixture of a compound of Formula 1 and a compound not corresponding to the present invention. Among them, the compounds not corresponding to the present invention may be a single compound and may be two or more types of compounds. Here, when the compound is included in a combination of two or more types of other compounds, the other compounds may be known compounds for each organic material layer or may be compounds to be developed in the future. Among them, the compounds contained in the organic material layer may be composed of only the same type of compounds, but may also be a mixture of two or more different compounds represented by Formula 1.

[0057] Hereinafter, compounds, compositions and organic electronic elements containing the same according to aspects of the present invention will be described.

[0058] The present invention provides a composition for an organic electronic element, the composition comprising a mixture of a compound represented by Formula 1 and a compound represented by Formula 5.

[0059] Formula 1

[0060]

[0061] Formula 5

[0062]

[0063] Wherein:

[0064] R 1 、R 2 、R 3 、R 4 、R 5 、R 6 and R 7 are the same as or different from each other and are each independently hydrogen or deuterium;

[0065] The *a bond is bonded to *b or *c,

[0066] *d is bonded to *e or *f,

[0067] a and e are independently integers from 0 to 5, b and f are independently integers from 0 to 4, c, d and g are independently integers from 0 to 3,

[0068] L 15 each independently selected from: a single bond; C 6 -C 60 an arylene group; a fluorenylene group; a C 2 -C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si or P; and a C 3 -C 60 aliphatic ring and a C 6 -C 60 fused ring group of an aromatic ring;

[0069] wherein when L 15 is an arylene group, it may preferably be a C 6 -C 30 arylene group, more preferably a C 6 -C 25 arylene group, for example, phenylene, biphenylene, naphthylene, terphenylene, anthrylene, etc.,

[0070] wherein when L 15 is a heterocyclic group, it may preferably be a C 2 -C 30 heterocyclic group, and more preferably a C 2 -C 24 heterocyclic group, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, benzocarbazole, naphthobenzofuran, naphthobenzothiophene, etc.,

[0071] wherein when L 15 is a fused ring group, it may preferably be a C 3 -C 30 aliphatic ring and a C 6 -C 30 fused ring group of an aromatic ring, more preferably a C 3 -C 24 aliphatic ring and a C 6 -C 24 fused ring group of an aromatic ring,

[0072] Ar 15 each independently selected from: C 6 -C 60Aryl group; fluorenyl group; C containing at least one heteroatom selected from O, N, S, Si or P 2 -C 60 Heterocyclic group; C 3 -C 60 Aliphatic ring; C 3 -C 60 Aliphatic ring and C 6 -C 60 Fused ring group of aliphatic ring and aromatic ring; and -L'-N(R')(R");

[0073] Wherein when Ar 15 is an aryl group, it may preferably be C 6 -C 30 Aryl group, more preferably C 6 -C 25 Aryl group, for example, it may be phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, benzophenanthrene, etc.,

[0074] Wherein when Ar 15 is a heterocyclic group, it may preferably be C 2 -C 30 Heterocyclic group, more preferably C 2 -C 24 Heterocyclic group, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzquinazoline, carbazole, dibenzquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.,

[0075] Wherein when Ar 15 is an aliphatic ring group, it is preferably C 3 -C 30 Aliphatic ring group, more preferably C 3 -C 24 Aliphatic ring group.

[0076] Wherein when Ar 15 is a fused ring group, it is preferably C 3 -C 30 Aliphatic ring and C 6 -C 30 Fused ring group of aliphatic ring and aromatic ring, more preferably C 3 -C 24 Aliphatic ring and C 6 -C 24 Fused ring group of aliphatic ring and aromatic ring,

[0077] Wherein L' is selected from: single bond; C 6 -C 60Arylene group; fluorene-9,9-diyl group; C containing at least one heteroatom selected from O, N, S, Si or P 2 -C 60 Heterocyclic group; and C 3 -C 60 Aliphatic ring;

[0078] Wherein when L' is an arylene group, it may preferably be C 6 -C 30 Arylene group, more preferably C 6 -C 25 Arylene group, for example, phenylene, biphenylene, naphthylene, terphenylene, anthrylene, etc.,

[0079] Wherein when L' is a heterocyclic group, it may preferably be C 2 -C 30 Heterocyclic group, and more preferably C 2 -C 24 Heterocyclic group, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, phenothiazine, phenylphenothiazine, benzocarbazole, naphthobenzofuran, naphthobenzothiophene, etc.,

[0080] Wherein when L' is an aliphatic ring group, it is preferably C 3 -C 30 Aliphatic ring group, more preferably C 3 -C 24 Aliphatic ring group,

[0081] Wherein R' and R" are each independently selected from: C 6 -C 60 Aryl group; fluorene group; C containing at least one heteroatom selected from O, N, S, Si or P 2 -C 60 Heterocyclic group; C 3 -C 60 Aliphatic ring group; and C 3 -C 60 Aliphatic ring and C 6 -C 60 Fused ring group of an aromatic ring;

[0082] Wherein when R' and R” are aryl groups, it may preferably be C 6 -C 30 Aryl group, more preferably C 6 -C 25An aryl group, for example, it can be phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, benzophenanthrene, etc.,

[0083] wherein when R' and R” are heterocyclic groups, it can preferably be C 2 -C 30 a heterocyclic group, and more preferably C 2 -C 24 a heterocyclic group, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzquinazoline, carbazole, dibenzquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.,

[0084] wherein when R' and R” are aliphatic ring groups, it is preferably C 3 -C 30 an aliphatic ring group, more preferably C 3 -C 24 an aliphatic ring group,

[0085] wherein when R' and R” are fused ring groups, it is preferably C 3 -C 30 an aliphatic ring and C 6 -C 30 a fused ring group of an aromatic ring, more preferably C 3 -C 24 an aliphatic ring and C 6 -C 24 a fused ring group of an aromatic ring,

[0086] Y 10 is O, S, CR 51 R 52 or NR 53 ,

[0087] Ring B is C 6 -C 20 an aryl group,

[0088] R 31 and R 32 are each the same or different, and each independently selected from: hydrogen; deuterium; halogen; cyano group; nitro group; C 6 -C 60 an aryl group; a fluorenyl group; a C 2 -C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si or P; C 3 -C 60 an aliphatic ring and C 6 -C 60Fused ring group of an aromatic ring; C 1 -C 50 Alkyl group; C 2 -C 20 Alkenyl group; C 2 -C 20 Alkynyl group; C 1 -C 30 Alkoxy group; and C 6 -C 30 Aryloxy group; or multiple adjacent R 31 or multiple R 32 can be bonded to each other to form a ring,

[0089] R 51 、R 52 and R 53 are each independently selected from: C 6 -C 60 Aryl group; Fluorenyl group; C containing at least one heteroatom of O, N, S, Si or P 2 -C 60 Heterocyclic group; C 3 -C 60 Aliphatic ring and C 6 -C 60 Fused ring group of an aromatic ring; C 1 -C 50 Alkyl group; C 2 -C 20 Alkenyl group; C 2 -C 20 Alkynyl group; C 1 -C 30 Alkoxy group; and C 6 -C 30 Aryloxy group; or, R 51 and R 52 can be bonded to each other to form a spiro ring,

[0090] wherein when R 31 、R 32 、R 51 、R 52 and R 53 are aryl groups, preferably C 6 -C 30 aryl group, more preferably C 6 -C 25 aryl group, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.

[0091] wherein when R 31 、R 32 、R 51 、R 52 and R53 When it is a heterocyclic group, it is preferably a C 2 -C 30 heterocyclic group, and more preferably a C 2 -C 24 heterocyclic group, such as pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzquinazoline, carbazole, dibenzquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.,

[0092] wherein when R 31 , R 32 , R 51 , R 52 and R 53 are fused ring groups, it is preferably a C 3 -C 30 aliphatic ring and a C 6 -C 30 aromatic ring fused ring group, more preferably a C 3 -C 24 aliphatic ring and a C 6 -C 24 aromatic ring fused ring group,

[0093] wherein when R 31 , R 32 , R 51 , R 52 and R 53 are alkyl groups, it can preferably be a C 1 -C 30 alkyl group, and more preferably a C 1 -C 24 alkyl group,

[0094] wherein when R 31 , R 32 , R 51 , R 52 and R 53 are alkoxy groups, they can preferably be a C 1 -C 24 alkoxy group,

[0095] wherein when R 31 , R 32 , R 51 , R 52 and R 53 are aryloxy groups, it can preferably be a C 6 -C 24 aryloxy group,

[0096] ba and bb are each independently an integer from 0 to 4,

[0097] wherein 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 may be substituted with one or more substituents selected from: deuterium; halogen; silyl group; siloxy group; boron group; germanium group; cyano group; nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; C 1 -C 20 alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkynyl group; C 6 -C 20 aryl group; C substituted with deuterium 6 -C 20 aryl group; fluorenyl group; C 2 -C 20 heterocyclic group; C 3 -C 20 cycloalkyl group; C 7 -C 20 arylalkyl group; C 8 -C 20 arylalkenyl group; and -L'-N(R')(R"); in addition, the hydrogen of these substituents may be further substituted with one or more deuteriums, and the substituents may be bonded to each other to form a saturated or unsaturated ring, where the term "ring" means C 3 -C 60 aliphatic ring or C 6 -C 60 aromatic ring or C 2 -C 60 heterocyclic group or a fused ring formed by their combination.

[0098] Preferably, the composition for an organic electronic device can be used as a host for a light-emitting layer.

[0099] In addition, Formula 1 includes a compound selected from any one of Formulas 1-1 to 1-4.

[0100]

[0101]

[0102] wherein R 1 、R 2 、R3 , R 4 , R 5 , R 6 , R 7 , a, b, c, d, e, f, and g are the same as those defined in Formula 1.

[0103] Specifically, the compound represented by Formula 1 can be any one of the following compounds P-1 to P-100, but is not limited thereto.

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111] Preferably, Formula 1 can be a compound represented by any one of Compounds P-5 to P-100.

[0112] Formula 5 can be represented by any one of Formulas 5-1 to 5-6.

[0113]

[0114]

[0115] Wherein:

[0116] Y 10 , L 15 , Ar 15 , R 31 , R 32 , ba, and bb are the same as those defined in Formula 5,

[0117] R 39 has the same definition as R 31 , or multiple adjacent Rs 39 can be bonded to each other to form a ring,

[0118] bi is an integer from 0 to 2.

[0119] Formula 5 can be represented by any one of Formulas 5-7 to 5-9.

[0120]

[0121] <Formula 5-9>

[0122]

[0123] Wherein:

[0124] Y 10 , L 15 , Ar 15 , Ring B, R 32 and bb are the same as defined in Formula 5,

[0125] R 40 is the same as the definition of R 31 , or multiple adjacent Rs 40 can be bonded to each other to form a ring,

[0126] bj is an integer from 0 to 6.

[0127] Formula 5 can be represented by any one of Formulas 5-10 to 5-12.

[0128]

[0129] <Formula 5-12>

[0130]

[0131] Wherein:

[0132] Y 10 , L 15 , Ar 15 , Ring B, R 31 and ba are the same as defined in Formula 5,

[0133] R 41 is the same as the definition of R 31 , or multiple adjacent Rs 41 can be bonded to each other to form a ring,

[0134] bk is an integer from 0 to 6.

[0135] Formula 5 can be represented by any one of Formulas 5-13 to 5-18.

[0136]

[0137] Wherein:

[0138] Y 10 , L 15 , Ar 15 , R 31 , R 32 , ba and bb are the same as defined in Formula 5,

[0139] R39 , R 40 and R 41 is the same as R 31 or multiple adjacent Rs 39 or multiple Rs 40 or multiple Rs 41 can be bonded to each other to form a ring,

[0140] Independently of each other, bi is an integer from 0 to 2, and bj and bk are integers from 0 to 6.

[0141] Formula 5 can be represented by Formula 5-19.

[0142] <Formula 5-19>

[0143]

[0144] where:

[0145] L 15 , Ar 15 , R 53 , R 32 and bb are the same as those defined in Formula 5,

[0146] R 39 and R 40 is the same as R 31 or multiple adjacent Rs 39 or multiple Rs 40 can be bonded to each other to form a ring,

[0147] bi is an integer from 0 to 2, and bj is an integer from 0 to 6.

[0148] Specifically, the compound represented by Formula 5 can be any one of the following Compounds S-1 to S-116, but is not limited thereto.

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156] In addition, on the other hand, the present invention provides an organic electronic element, comprising: a first electrode; a second electrode; and an organic material layer formed between the first electrode and the second electrode; wherein the organic material layer contains a composition for an organic electronic element or a compound represented by Formula 1.

[0157] On the other hand, the present invention provides a method for recycling the compound of Formula 1, comprising:

[0158] recovering a crude organic light-emitting material containing the compound of Formula 1 from a deposition apparatus used in a process for depositing an organic light-emitting material to prepare an organic light-emitting device;

[0159] removing impurities from the crude organic light-emitting material;

[0160] recovering the organic light-emitting material after removing the impurities; and

[0161] purifying the recovered organic light-emitting material to a purity of 99.9% or higher.

[0162] The step of removing impurities from the crude organic light-emitting material recovered from the deposition apparatus may preferably include a pre-purification process of recrystallization in a recrystallization solvent to obtain a purity of 98% or higher.

[0163] The recrystallization solvent may preferably be a polar solvent having a polarity index (PI) value of 5.5 to 7.2.

[0164] The recrystallization solvent may preferably be used by mixing a polar solvent having a polarity index value of 5.5 to 7.2 and a non-polar solvent having a polarity index value of 2.0 to 4.7.

[0165] When using a mixture of a polar solvent and a non-polar solvent, the recrystallization solvent may be used in an amount such that the non-polar solvent is 15% (v / v) or less compared to the polar solvent.

[0166] The recrystallization solvent is preferably a single solvent of N-methylpyrrolidone (NMP); or a polar solvent in which any one selected from 1,3-dimethyl-2-imidazolidinone, 2-pyrrolidone, N,N-dimethylformamide, dimethylacetamide, and dimethyl sulfoxide is mixed into N-methylpyrrolidone; or a single solvent or a mixed non-polar solvent selected from toluene, dichloromethane (DCM), dichloroethane (DCE), tetrahydrofuran (THF), chloroform, ethyl acetate, and methyl ethyl ketone; or a mixture of a polar solvent and a non-polar solvent.

[0167] The pre-purification process may include a step of dissolving the crude organic light-emitting material recovered from the deposition apparatus in a polar solvent at 90°C to 120°C and then precipitating crystals by cooling to 0°C to 5°C.

[0168] The pre-purification process may include the steps of dissolving the crude organic light-emitting material recovered from the deposition apparatus in a polar solvent at 90 °C to 120 °C, and then precipitating crystals by cooling to 35 °C to 40 °C, adding a non-polar solvent, and then cooling to 0 °C to 5 °C.

[0169] The pre-purification process may include the steps of dissolving the crude organic light-emitting material recovered from the deposition apparatus in a non-polar solvent, and then precipitating crystals while concentrating the solvent and removing the non-polar solvent.

[0170] The pre-purification process may include the steps of recrystallizing first with a polar solvent and then with a non-polar solvent.

[0171] The step of purifying the recovered organic light-emitting material to a purity of 99.9% or higher may include an adsorption separation process of adsorbing and removing impurities by adsorption on an adsorbent.

[0172] The adsorbent may be activated carbon, silica gel, alumina, or a material for known adsorption purposes.

[0173] The step of purifying the recovered organic light-emitting material to a purity of 99.9% or higher may include performing sublimation purification.

[0174] Reference Figure 1 , the organic electronic device 100 according to the present invention includes a first electrode 110, a second electrode 170, and an organic material layer between the first electrode 110 and the second electrode 170, which contains a single compound represented by Formula 1 or two or more compounds. Among them, the first electrode 110 may be an anode or a positive electrode, and the second electrode 170 may be a cathode or a negative electrode. In the case of an inverted organic electronic device, the first electrode may be a cathode, and the second electrode may be an anode.

[0175] The organic material 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. Here, the remaining layers except the light-emitting layer 140 may not be formed. The organic material layer may further include a hole blocking layer, an electron blocking layer, a light-emitting auxiliary layer 220, a buffer layer 210, etc., and the electron transport layer 150, etc. may be used as a hole blocking layer (see Figure 2 ).

[0176] In addition, the organic electronic device according to an embodiment of the present invention may further include a protective layer or a light efficiency enhancing layer 180. The light efficiency enhancing layer may be formed on a surface of the first electrode that does not contact the organic material layer or on a surface of the second electrode that does not contact the organic material layer. The compound or material for an organic electronic device according to an embodiment of the present invention applicable to the organic material layer may be used as a host or a dopant for the hole injection layer 120, the hole transport layer 130, the light emitting auxiliary layer 220, the electron transport auxiliary layer, the electron transport layer 150, the electron injection layer 160, the light emitting layer 140, or a material for the light efficiency enhancing layer. Preferably, for example, the composition for an organic electronic device of the present invention or the compound represented by Formula 1 may be used as a host material for the light emitting layer.

[0177] The organic material layer may include two or more stacked bodies, the stacked body including a hole transport layer, a light emitting layer, and an electron transport layer formed in sequence on the anode, and may further include a charge generation layer formed between two or more stacked bodies (see Figure 3 ).

[0178] In addition, even when using the same parent nucleus, the band gap, electrical properties, interface properties, etc. may vary depending on the position where the substituent is bonded. Therefore, the selection of the combination of the parent nucleus and the sub-substituents connected thereto is also very important. In particular, when achieving an optimal combination of the energy levels and T1 values of each organic material layer and the unique properties (mobility, interface properties, etc.) of the material, long service life and high efficiency can be achieved simultaneously.

[0179] The organic electroluminescent device according to an embodiment of the present invention may 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 a cathode, and an organic material 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, whereby the organic electroluminescent device according to an embodiment of the present invention can be manufactured.

[0180] In addition, the present invention provides an organic electronic device, wherein the organic material layer is formed by one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, or a roll-to-roll process, and the organic material layer provides an organic electronic device including a compound or a composition for an organic electronic device as an electron transport material.

[0181] As another specific example, the present invention provides an organic electronic device, which uses the organic electronic device by mixing the same or different compounds represented by Formula 1 into an organic material layer. Preferably, the organic material layer includes a light-emitting layer, and the light-emitting layer contains a composition for the organic electronic device or a compound represented by Formula 1.

[0182] In addition, the present invention provides a composition for an organic electronic device or a compound represented by Formula 1, and provides an organic electronic device including the composition for an organic electronic device or a compound represented by Formula 1.

[0183] In addition, the present invention also provides an electronic device, including a display device and a control unit for driving the display device, and the display device includes an organic electronic device.

[0184] According to another aspect, the present invention provides a display device, wherein the organic electronic device is at least one of an OLED, an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and an element for monochromatic or white lighting. Here, the electronic device may be a wired / wireless communication terminal currently in use or to be used in the future, and covers all kinds of electronic devices, including mobile communication terminals such as mobile phones, personal digital assistants (PDAs), electronic dictionaries, point-to-multipoint (PMP), remote controllers, navigation units, game consoles, various televisions, and various computers.

[0185] Hereinafter, synthesis examples of compounds represented by Formula 1 and Formula 5 and preparation examples of organic electronic devices according to the present invention will be described in detail by way of examples, but are not limited to the following examples.

[0186] [Synthesis Example 1] Compound Represented by Formula 1

[0187] The compound (end product) represented by Formula 1 according to the present invention is synthesized as shown in Reaction Scheme 1, but is not limited thereto.

[0188] <Reaction Scheme 1>

[0189]

[0190] Wherein, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , a, b, c, d, e, f, g, *a, *b, *c, *d, *e, and *f are the same as those defined in Formula 1.

[0191] I. Synthesis of End Product

[0192] 1. Synthesis Example of P-1

[0193]

[0194] Sub 1-1 (50.0 g, 126.9 mmol) was added to a round-bottom flask and dissolved in THF (635 ml). Sub 2-1 (47.0 g, 126.9 mmol), Pd(PPh 3 ) 4 (8.8 g, 7.6 mmol), NaOH (15.2 g, 380.8 mmol), and water (317 ml) were added to the round-bottom flask and the reaction was carried out at 80 °C. When the reaction was completed, the organic layer was extracted with CH 2 Cl 2 and water, dried over MgSO 4 , concentrated, and the resulting organic material was recrystallized using a silica gel column to obtain 62.9 g of the product. (Yield: 82.4%)

[0195] 2. Synthesis Example of P-2

[0196]

[0197] 1) Synthesis of Sub 1-2-b

[0198] Sub 1-2-a (100.0 g, 418.9 mmol) was added to a round-bottom flask and dissolved in DMF (2094 ml). 4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bis(1,3,2-dioxaborolane) (138.3 g, 544.59 mmol), Pd(dppf)Cl 2 (15.33 g, 21.0 mmol), and KOAc (123.4 g, 1256.8 mmol) were added and stirred at 150 °C for 2 hours. When the reaction was completed, the organic layer was extracted with CH 2 Cl 2 and water, dried over MgSO 4 , concentrated, and the resulting organic material was recrystallized using a silica gel column to obtain 112.88 g of the product. (Yield: 81.6%)

[0199] 2) Synthesis of Sub 1-2

[0200] Sub 1-2-b (70.0 g, 212.0 mmol) was added to a round-bottom flask and dissolved in THF (1060 ml). Sub 1-2-c (47.9 g, 212.0 mmol), Pd(PPh 3 ) 4(14.7 g, 12.7 mmol), NaOH (25.4 g, 635.9 mmol), water (530 ml), and the experiment was carried out in the same manner as P-1 to obtain 69.4 g of the product. (Yield: 83.1%)

[0201] 3) Synthesis of P-2

[0202] Sub 1-2 (60.0 g, 152.3 mmol) was added to a round-bottom flask and dissolved in THF (762 ml), and Sub 2-1 (56.4 g, 152.3 mmol), Pd(PPh 3 ) 4 (9.1 g, 10.6 mmol), NaOH (18.3 g, 457.0 mmol), water (381 ml), and the experiment was carried out in the same manner as P-1 to obtain 74.7 g of the product. (Yield: 81.5%)

[0203] 3. Synthesis Example of P-3

[0204]

[0205] Sub 1-1 (50.0 g, 126.9 mmol) was added to a round-bottom flask and dissolved in THF (635 ml), and Sub 2-2 (47.0 g, 126.9 mmol), Pd(PPh 3 ) 4 (8.8 g, 7.6 mmol), NaOH (15.2 g, 380.8 mmol), water (317 ml), and the experiment was carried out in the same manner as P-1 to obtain 62.6 g of the product. (Yield: 82.0%)

[0206] 4. Synthesis Example of P-4

[0207]

[0208] Sub 1-2 (50.0 g, 126.9 mmol) was added to a round-bottom flask and dissolved in THF (635 ml), and Sub 2-2 (47.0 g, 126.9 mmol), Pd(PPh 3 ) 4 (8.8 g, 7.6 mmol), NaOH (15.2 g, 380.8 mmol), water (317 ml), and the experiment was carried out in the same manner as P-1 to obtain 62.4 g of the product. (Yield: 81.7%)

[0209] 5. Synthesis Example of P-5

[0210]

[0211] 1) Synthesis of Sub 1-3-a

[0212] Add Sub 1-3-a-a (100.0 g, 478.2 mmol) to a round-bottom flask and dissolve it in THF (2391 ml). Then add Sub 1-3-a-b (94.2 g, 478.2 mmol), Pd(PPh 3 ) 4 (33.2 g, 28.7 mmol), NaOH (57.4 g, 1434.7 mmol), water (1196 ml), and conduct the experiment in the same manner as P-1 to obtain 90.1 g of the product. (Yield: 77.3%)

[0213] 2) Synthesis of Sub 1-3-b

[0214] Add Sub 1-3-a (70.0 g, 287.2 mmol) to a round-bottom flask and dissolve it in DMF (1436 ml). Then add 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (94.8 g, 373.35 mmol), Pd(dppf)Cl 2 (10.5 g, 14.4 mmol), KOAc (84.6 g, 861.6 mmol), and conduct the experiment in the same manner as Sub 1-2-b to obtain 77.6 g of the product. (Yield: 80.6%)

[0215] 3) Synthesis of Sub 1-3

[0216] Add Sub 1-3-b (70.0 g, 208.8 mmol) to a round-bottom flask and dissolve it in THF (1044 ml). Add Sub 1-2-c (47.2 g, 208.8 mmol), Pd(PPh 3 ) 4 (14.5 g, 12.5 mmol), NaOH (25.1 g, 626.4 mmol), water (522 ml), and conduct the experiment in the same manner as P-1 to obtain 67.6 g of the product. (Yield: 81.2%)

[0217] 4) Synthesis of P-5

[0218] Add Sub 1-3 (60.0 g, 150.4 mmol) to a round-bottom flask and dissolve it in THF (752 ml). Add Sub 2-1 (55.7 g, 150.4 mmol), Pd(PPh3 ) 4 (10.4 g, 9.0 mmol), NaOH (18.0 g, 451.2 mmol), water (376 ml), and the experiment was conducted in the same manner as P-1 to obtain 73.7 g of the product. (Yield: 80.8%)

[0219] 6. Synthesis Example of P-13

[0220]

[0221] 1) Synthesis of Sub 1-5-a

[0222] Sub 1-5-a-a (100.0 g, 490.0 mmol) was added to a round-bottom flask and dissolved in THF (2450 ml), and Sub 1-5-a-b (99.5 g, 490.0 mmol), Pd(PPh 3 ) 4 (34.0 g, 28.7 mmol), NaOH (58.8 g, 1470.0 mmol), water (1225 ml), and the experiment was conducted in the same manner as P-1 to obtain 92.2 g of the product. (Yield: 76.9%)

[0223] 2) Synthesis of Sub 1-5-b

[0224] Sub 1-5-a (70.0 g, 286.0 mmol) was added to a round-bottom flask and dissolved in DMF (1430 ml), and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (94.4 g, 371.8 mmol), Pd(dppf)Cl 2 (10.5 g, 14.3 mmol), KOAc (84.2 g, 858.0 mmol) were added, and the experiment was conducted in the same manner as Sub 1-2-b to obtain 77.6 g of the product. (Yield: 80.7%)

[0225] 3) Synthesis of Sub 1-5

[0226] Sub 1-5-b (70.0 g, 208.2 mmol) was added to a round-bottom flask and dissolved in THF (1041 ml), Sub 1-2-c (47.1 g, 208.2 mmol), Pd(PPh 3 ) 4(14.4 g, 12.5 mmol), NaOH (25.0 g, 624.5 mmol), water (520 ml), and the experiment was carried out in the same manner as P-1 to obtain 66.9 g of the product. (Yield: 80.4%)

[0227] 4) Synthesis of P-13

[0228] Sub 1-5 (60.0 g, 150.0 mmol) was added to a round-bottom flask and dissolved in THF (750 ml), and Sub 2-1 (55.6 g, 150.0 mmol), Pd(PPh 3 ) 4 (10.4 g, 9.0 mmol), NaOH (18.0 g, 450.1 mmol), water (375 ml), and the experiment was carried out in the same manner as P-1 to obtain 73.9 g of the product. (Yield: 81.1%)

[0229] 7. Synthesis Example of P-21

[0230]

[0231] 1) Synthesis of Sub 1-7-a

[0232] Sub 1-3-a-a (100.0 g, 478.2 mmol) was added to a round-bottom flask and dissolved in THF (2391 ml), and Sub 1-5-a-b (97.1 g, 478.2 mmol), Pd(PPh 3 ) 4 (33.2 g, 28.7 mmol), NaOH (57.4 g, 1434.7 mmol), water (1196 ml), and the experiment was carried out in the same manner as P-1 to obtain 91.9 g of the product. (Yield: 76.9%)

[0233] 2) Synthesis of Sub 1-7-b

[0234] Sub 1-7-a (70.0 g, 280.2 mmol) was added to a round-bottom flask and dissolved in DMF (1401 ml), and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (92.5 g, 364.3 mmol), Pd(dppf)Cl 2 (10.2 g, 14.0 mmol), KOAc (82.5 g, 840.7 mmol) were added, and the experiment was carried out in the same manner as Sub 1-2-b to obtain 77.8 g of the product. (Yield: 81.3%)

[0235] 3) Synthesis of Sub 1-7

[0236] Add Sub 1-7-b (70.0 g, 205.1 mmol) to a round-bottom flask and dissolve it in THF (1025 ml). Add Sub 1-2-c (46.4 g, 205.1 mmol), Pd(PPh 3 ) 4 (14.2 g, 12.3 mmol), NaOH (24.6 g, 615.3 mmol), water (513 ml), and conduct the experiment in the same manner as P-1 to obtain 67.3 g of the product. (Yield: 81.0%)

[0237] 4) Synthesis of P-21

[0238] Add Sub 1-7 (60.0 g, 148.2 mmol) to a round-bottom flask and dissolve it in THF (741 ml). Add Sub 2-1 (54.9 g, 148.2 mmol), Pd(PPh 3 ) 4 (10.3 g, 8.9 mmol), NaOH (17.8 g, 444.5 mmol), water (370 ml), and conduct the experiment in the same manner as P-1 to obtain 73.7 g of the product. (Yield: 81.2%)

[0239] 8. Synthesis Example of P-30

[0240]

[0241] 1) Synthesis of Sub 2-6-a

[0242] Add Sub 2-6-a-a (100.0 g, 393.5 mmol) to a round-bottom flask and dissolve it in THF (1967 ml). Add Sub 2-6-a-b (93.9 g, 393.5 mmol), Pd(PPh 3 ) 4 (27.3 g, 23.6 mmol), NaOH (47.2 g, 1180.5 mmol), water (984 ml), and conduct the experiment in the same manner as P-1 to obtain 95.0 g of the product. (Yield: 84.5%)

[0243] 2) Synthesis of Sub 2-6

[0244] Sub 2-6-a (70.0 g, 244.9 mmol) was added to a round-bottom flask and dissolved in DMF (1225 ml), and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (80.9 g, 318.4 mmol), Pd(dppf)Cl 2 (9.0 g, 12.3 mmol), and KOAc (72.1 g, 734.8 mmol) were added, and the experiment was carried out in the same manner as Sub 1-2-b to obtain 75.9 g of the product. (Yield: 82.1%)

[0245] 3) Synthesis of P-30

[0246] Sub 2-6 (60.0 g, 159.0 mmol) was added to a round-bottom flask and dissolved in THF (795 ml), Sub 1-3 (63.4 g, 159.0 mmol), Pd(PPh 3 ) 4 (11.0 g, 9.5 mmol), NaOH (19.1 g, 477.1 mmol), and water (398 ml) were added, and the experiment was carried out in the same manner as P-1 to obtain 80.0 g of the product. (Yield: 82.0%)

[0247] 9. Synthesis Example of P-59

[0248]

[0249] 1) Synthesis of Sub 1-10-a

[0250] Sub 1-3-a-a (100.0 g, 478.2 mmol) was added to a round-bottom flask and dissolved in THF (2391 ml), and Sub 1-10-a-b (138.0 g, 478.2 mmol), Pd(PPh 3 ) 4 (33.2 g, 28.7 mmol), NaOH (57.4 g, 1434.7 mmol), and water (1196 ml) were added, and the experiment was carried out in the same manner as P-1 to obtain 94.2 g of the product. (Yield: 80.8%)

[0251] 2) Synthesis of Sub 1-10-b

[0252] Sub 1-10-a (70.0 g, 287.2 mmol) was added to a round-bottom flask and dissolved in DMF (1436 ml). 4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bis(1,3,2-dioxaborolane) (94.8 g, 373.35 mmol), Pd(dppf)Cl 2 (10.5 g, 14.4 mmol), and KOAc (84.6 g, 861.6 mmol) were added, and the experiment was carried out in the same manner as Sub 1-2-b to obtain 78.9 g of the product. (Yield: 81.9%)

[0253] 3) Synthesis of Sub 1-10

[0254] Sub 1-10-b (70.0 g, 208.8 mmol) was added to a round-bottom flask and dissolved in THF (1044 ml). Sub 1-10-c (48.3 g, 208.8 mmol), Pd(PPh 3 ) 4 (14.5 g, 12.5 mmol), NaOH (25.1 g, 626.4 mmol), and water (522 ml) were added, and the experiment was carried out in the same manner as P-1 to obtain 64.4 g of the product. (Yield: 82.4%)

[0255] 4) Synthesis of Sub 2-4-a

[0256] Sub 2-4-a-a (100.0 g, 404.7 mmol) was added to a round-bottom flask and dissolved in THF (2024 ml). Sub 2-4-a-b (98.2 g, 404.7 mmol), Pd(PPh 3 ) 4 (28.1 g, 24.3 mmol), NaOH (48.6 g, 1214.1 mmol), and water (1012 ml) were added, and the experiment was carried out in the same manner as P-1 to obtain 91.3 g of the product. (Yield: 79.8%)

[0257] 5) Synthesis of Sub 2-4

[0258] Sub 2-4-a (70.0 g, 247.6 mmol) was added to a round-bottom flask and dissolved in DMF (1238 ml), and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (81.7 g, 321.8 mmol), Pd(dppf)Cl 2(9.1 g, 12.4 mmol), KOAc (72.9 g, 742.7 mmol), and the experiment was carried out in the same manner as Sub 1-2-b to obtain 74.4 g of the product. (Yield: 80.3%)

[0259] 6) Synthesis of P-59

[0260] Sub 1-10 (60.0 g, 148.5 mmol) was added to a round-bottom flask and dissolved in THF (743 ml). Sub 2-4 (55.6 g, 148.5 mmol), Pd(PPh 3 ) 4 (10.3 g, 8.9 mmol), NaOH (17.8 g, 445.6 mmol), water (371 ml), and the experiment was carried out in the same manner as P-1 to obtain 74.6 g of the product. (Yield: 81.6%)

[0261] Sub 1 in Reaction Scheme 1 can be but is not limited to the following compounds, and the FD-MS (field desorption - mass spectrometry) values of the compounds belonging to Sub 1 are shown in Table 1.

[0262]

[0263]

[0264] [Table 1]

[0265] Compound FD-MS Compound FD-MS Sub 1-1 <![CDATA[m / z = 393.10 (C 25 H 16 ClN 3 = 393.87)]]> Sub 1-2 <![CDATA[m / z = 393.10 (C 25 H 16 ClN 3 = 393.87)]]> Sub 1-3 <![CDATA[m / z = 398.13 (C 25 H 11 D 5 ClN 3 = 398.90)]]> Sub 1-4 <![CDATA[m / z = 403.17 (C 25 H 6 D 10 ClN 3 = 403.94)]]> Sub 1-5 <![CDATA[m / z = 399.14 (C 25 H 10 D 6 ClN 3 = 399.91)]]> Sub 1-6 <![CDATA[m / z = 404.17 (C 25 H 5 D 11 ClN 3 = 404.94)]]> Sub 1-7 <![CDATA[m / z = 404.17 (C 25 H 5 D 11 ClN 3 = 404.94)]]> Sub 1-8 <![CDATA[m / z = 409.20 (C 25 D 16 ClN 3 = 409.97)]]> Sub 1-9 <![CDATA[m / z = 398.13 (C 25 H 11 D 5 ClN 3 = 398.90)]]> Sub 1-10 <![CDATA[m / z = 403.17 (C 25 H 6 D 10 ClN 3 = 403.94)]]> Sub 1-11 <![CDATA[m / z = 399.14 (C 25 H 10 D 6 ClN 3 = 399.91)]]> Sub 1-12 <![CDATA[m / z = 404.17 (C 25 H 5 D 11 ClN 3 = 404.94)]]> Sub 1-13 <![CDATA[m / z = 404.17 (C 25 H 5 D 11 ClN 3 = 404.94)]]> Sub 1-14 <![CDATA[m / z = 409.20 (C 25 D 16 ClN 3 = 409.97)]]>

[0266] Sub 2 in Reaction Scheme 1 can be but is not limited to the following compounds, and the FD-MS (field desorption - mass spectrometry) values of the compounds belonging to Sub 2 are shown in Table 2.

[0267]

[0268]

[0269] [Table 2]

[0270] Compound FD-MS Compound FD-MS Sub 2-1 <![CDATA[m / z = 370.17 (C 24 H 23 BO 3 = 370.26)]]> Sub 2-2 <![CDATA[m / z = 370.17 (C 24 H 23 BO 3 = 370.26)]]> Sub 2-3 <![CDATA[m / z = 377.22 (C 24 H 16 D 7 BO 3 = 377.30)]]> Sub 2-4 <![CDATA[m / z = 374.20 (C 24 H 19 D 4 BO 3 = 374.28)]]> Sub 2-5 <![CDATA[m / z = 381.24 (C 24 H 12 D 11 BO 3 = 381.32)]]> Sub 2-6 <![CDATA[m / z = 377.22 (C 24 H 16 D 7 BO 3 = 377.30)]]> Sub 2-7 <![CDATA[m / z = 374.2 (C 24 H 19 D 4 BO 3 = 374.28)]]> Sub 2-8 <![CDATA[m / z = 381.24 (C 24 H 12 D 11 BO 3 = 381.32)]]>

[0271] The FD-MS (field desorption - mass spectrometry) values of Compounds P-1 to P-100 of the present invention prepared according to the above synthesis examples are shown in Table 3.

[0272] [Table 3]

[0273]

[0274]

[0275]

[0276] The compound represented by Formula 5 can be prepared by known synthetic methods (named reactions) or by referring to publicly available patent publications, such as Korean Patent Registration No. 10-2395819 and US Patent Publication No. 2023-0129535, but not limited thereto.

[0277] Meanwhile, the FD-MS (field desorption-mass spectrometry) values of Compounds S-1 to S-108 of the present invention are shown in Table 4.

[0278] [Table 4]

[0279]

[0280]

[0281]

[0282] Above, exemplary synthesis examples of the present invention represented by Formula 1 and Formula 5 have been described, but all of these are based on Buchwald-Hartwig cross-coupling reaction, Miyaura borylation 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 PPh 3 -mediated reductive cyclization reaction (J. Org. Chem. 2005, 70, 5014.), and it should be readily understood by those skilled in the art that the reaction can also proceed even when other substituents defined in Formula 1 or Formula 5 are bonded in addition to the substituents specified in the specific synthesis examples.

[0283] Manufacture and Evaluation of Organic Electronic Components

[0284] [Example 1] Red Organic Light-Emitting Device (Phosphorescent Host)

[0285] Compound A and Compound B were used on an 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 to form a hole transport layer with a thickness of 110 nm.

[0286] Next, compound C-R was vacuum deposited on the hole transport layer to a thickness of 10 nm to form an emission assisting layer. Thereafter, as the host materials of the light-emitting layer, compound P-1 (the compound of the present invention) was used as the first host, and compound S-32 (the compound of the present invention) was used as the second host, and a mixture in which the first host and the second host were mixed at a weight ratio of 5:5 was used. Bis-(1-phenylisoquinolinato)iridium(III) acetylacetonate (abbreviated as “(piq)2Ir(acac)” hereinafter) was used as the dopant material, and the dopant was doped such that the weight ratio of the host to the dopant was 95:5 to form a light-emitting layer having a thickness of 30 nm.

[0287] Next, compound E was vacuum deposited on the light-emitting layer to form a hole blocking layer having 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 transport layer having a thickness of 30 nm on the hole blocking layer. Thereafter, compound G was deposited on the electron transport layer to form an electron injection layer having a thickness of 0.2 nm, and then Al was deposited to form a cathode having a thickness of 150 nm.

[0288] Compound A: N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine

[0289] Compound B: 4,4',4”-((1E,1'E,1”E)-cyclopropane-1,2,3-triyltris(cyanomethylidene))tris(2,3,5,6-tetrafluorobenzonitrile)

[0290] Compound C-R: N 7 -(dibenzo[b,d]thiophen-2-yl)-N 2 ,N 2 ,N 7 -triphenyldibenzo[b,d]thiophene-2,7-diamine

[0291] Compound E: 2-(4'-(9,9-dimethyl-9H-fluorene-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine

[0292] Compound F: 2,7-bis(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalene

[0293] Compound G: lithium (8-hydroxyquinoline)

[0294] [Example 2] to [Example 55]

[0295] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that the compound of the present invention described in Table 5 was used as the host material of the light-emitting layer.

[0296] [Comparative Example 1] to [Comparative Example 9]

[0297] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that Comparative Compound A to Comparative Compound C as the first host, or Comparative Compound 1 or Comparative Compound 2 as the second host, was used as the host material of the light-emitting layer.

[0298]

[0299] [Comparative Compound C]

[0300]

[0301]

[0302]

[0303] [Example 56]

[0304] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that the compound P-1 of the present invention was used as the host material of the light-emitting layer without a second host.

[0305] [Example 57] to [Example 76]

[0306] An organic electroluminescent device was fabricated in the same manner as in Example 56, except that the compounds of the present invention described in Table 6 were used as the host material of the light-emitting layer.

[0307] [Comparative Example 10] to [Comparative Example 12]

[0308] An organic electroluminescent device was fabricated in the same manner as in Example 56, except that one of Comparative Compound A, Comparative Compound B, and Comparative Compound D was used as the host material of the light-emitting layer.

[0309] [Comparative Compound D]

[0310]

[0311] Electroluminescence (EL) characteristics were measured by applying a forward-biased DC voltage to the organic electroluminescent devices fabricated in Examples 1 to 76 and Comparative Examples 1 to 12 of the present invention using a PR-650 from Photoresearch, and the service life was measured using a service life measuring device manufactured by Maxscience at 2500 cd / m 2Measure the T95 service life at the reference brightness. Tables 5 and 6 show the results of manufacturing and evaluating the components according to the embodiments.

[0312] This measuring device allows the evaluation of the performance of new materials for reference compounds under the same conditions, without being affected by possible daily variations in deposition rate, vacuum quality, or other parameters.

[0313] Since one batch contains 4 identically prepared OLEDs containing the comparative compound during the evaluation, and the performance of a total of 12 OLEDs is evaluated in 3 batches, the values of the experimental results obtained in this way show statistical significance.

[0314] [Table 5]

[0315]

[0316]

[0317]

[0318] [Table 6]

[0319]

[0320]

[0321] To explain the results in Tables 5 and 6, the structure of the compound represented by Formula 1 of the present invention is interpreted as Figure 5 Structure 1 and Structure 2.

[0322] First, we explain the results in Table 5.

[0323] From the results in Table 5, it can be seen that compared with the comparative examples in which Comparative Compound A to Comparative Compound C having a basic skeleton similar to that of the compound of the present invention are used as the first host, or Comparative Compound 1 or Comparative Compound 2 is used as the second host, when the material for an organic electroluminescent device of the present invention is used as the host material of the light-emitting layer to manufacture a red organic electroluminescent device, the driving voltage, luminous efficiency, and service life of the organic electroluminescent device can be improved.

[0324] Comparative Compound A to Comparative Compound C can be regarded as structural isomers having a molecular weight and skeleton similar to those of the compound represented by Formula 1 of the present invention, but not having the same composition as Formula 1 of the present invention.

[0325] To confirm the energy level difference of the compounds caused by these differences, the data measured using the DFT method (B3LYP / 6-31g(D)) of the Gaussian program are shown in Table 7.

[0326] [Table 7]

[0327] Comparative Compound A Comparative Compound B Comparative Compound C P-1 LUMO (eV) -1.9829 -1.9973 -2.0580 -1.9693

[0328] As can be seen from the results in Table 7, the LUMO energy levels of the compound represented by Formula 1 of the present invention and the comparative compounds are formed differently.

[0329] To explain in more detail, the compound represented by Formula 1 of the present invention and Comparative Compounds A to C are used as an electron transport host in the light-emitting layer, but the LUMO energy levels formed in the case of Comparative Compounds A to C are deeper than the LUMO energy level of the compound represented by Formula 1 of the present invention, such that excessive electron injection into the light-emitting layer occurs, thereby disrupting the charge balance of the device. In contrast, the LUMO energy level of the compound represented by Formula 1 of the present invention is an intermediate value between the electron transport region and the dopant of the light-emitting layer, such that electrons in the electron transport region can be prevented from directly accumulating in the dopant of the light-emitting layer, and since the formation of exciplexes between the first host and the second host is promoted, the charge balance is optimized, and thus it appears to have an impact on the operation, efficiency, and service life of the device.

[0330] When Comparative Compound 1 and Comparative Compound 2 are used as the second host of the light-emitting layer, due to the characteristics of the amine groups present in the molecule, hole injection into the light-emitting layer occurs too quickly, thereby disrupting the charge balance of the device. However, when the compound represented by Formula 5 of the present invention is used as the second host, appropriate hole injection into the light-emitting layer is possible, and since the structural stability is increased compared to the amine structure, when used together with the compound represented by Formula 1 of the present invention as the first host for the light-emitting layer, the charge balance is maximized, and it appears to increase the operation, efficiency, and service life of the device.

[0331] Next, we explain the results in Table 6.

[0332] First, in the cases of Comparative Example 10 and Comparative Example 11, as materials different from the skeleton of the compound represented by Formula 1 of the present invention, the energy levels of the compounds are formed differently from those of the compounds of the present invention. Therefore, even when Comparative Compounds A and B are used as the sole hosts of the light-emitting layer, the charge balance of the device is not correct compared to the compounds having the skeleton of the compounds of the present invention, as explained by the results in Table 7.

[0333] The compounds of Comparative Example 12 are different from the compounds of Examples 56 to 76 in terms of the presence or absence of deuterium substitution or the position of deuterium substitution.

[0334] To confirm the change in the properties of the compounds according to the position of deuterium substitution, data on the electron cloud of the compounds were measured using the DFT method (B3LYP / 6-31g(D)) of the Gaussian program atFigure 6 shown, and the data of the measured IR spectrum are in Figures 7 to 9 shown.

[0335] First, Figure 6 is the LUMO electron cloud of the P-1 compound.

[0336] From Figure 6 it can be seen that it can be confirmed that the LUMO electron cloud is densely formed in the structure 1 part of formula 1 of the present invention. That is, the electrons from the electron transport region are transferred to the dopant through the structure 1 part of formula 1.

[0337] Since the deuterium-carbon bond length is usually shorter than the hydrogen-carbon bond length, a molecule having a deuterium-carbon bond has a reduced molecular hard-core volume, which can reduce the electronic polarizability.

[0338] This has the effect of reducing the crystallinity of the thin film, that is, an amorphous state is generated, which ultimately improves the electron mobility and significantly affects the service life of the device. It is judged that compared with the compound P-1 or the comparative compound D, the compounds P-5 to P-100 in which one or more deuterium atoms are substituted in the structure 1 part maximize the efficiency and service life in the device due to the effects described above.

[0339] Next, Figures 7 to 9 are the IR spectra of the compound P-1, the comparative compound D, and the compound P-21.

[0340] From Figures 7 to 9 it can be seen that depending on the deuterium substitution position of the compound, there are differences in the IR spectra. In Figure 7 (compound P-1) to Figure 9 (compound P-21), due to the C-H stretching mode, there is a peak near 3200 cm -1 , but the ε value near 3200 cm Figure 7 of the compound P-1 ( -1 ) without deuterium substitution is the largest. However, in the case of the comparative compound D ( Figure 8 ) with deuterium substitution and the compound P-21 ( Figure 9 ) of the present invention, the ε value near 3200 cm -1 decreases, and a peak generated by the C-D stretching mode is near 2400 cm -1 .

[0341] That is, compared with the non-deuterium-substituted compound P-1, the deuterium-substituted comparative compound D and the compound P-21 are structurally more stable because the high-frequency vibration is suppressed and the non-radiative decay is reduced, so the service life and efficiency of the device also seem to increase.

[0342] The similarity between Compound D and Compound P-21 is that they each have 11 deuterium atoms in the molecule. Their difference lies in that in the case of Compound D, deuterium substitution occurs in Structure 2, while in the case of Compound P-21, deuterium substitution occurs in Structure 1. From Figure 8 and Figure 9 it can be confirmed that the high-frequency vibration of Compound P-21 is suppressed to a greater extent than that of Comparative Compound D. That is, even though they are compounds with the same skeleton, among the compounds in which deuterium is substituted in Structure 1, namely Compounds P-5 to P-100, the high-frequency vibration suppression effect is greater. Therefore, the improvement effect on the service life and efficiency in the above-mentioned components is greater than that of the compounds in which deuterium is only substituted in Structure 2. This indicates that even for structural isomers with the same skeleton, the degree of change in the properties of the compound can vary according to the position of deuterium substitution, and thus the device results can also vary significantly.

[0343] That is, from Tables 5 to 7 and Figures 6 to 9 the results in it can be seen that even if the compounds have similar compositions, it can be confirmed that compared with other comparative compounds, the compounds of the present invention that satisfy all complex factors (such as the type of specific substituents and the substitution positions of the substituents) exhibit remarkable effects in organic electronic components. And through this, it can be seen that compared with the simple structural isomers or compounds with similar structures not described in this specification, the compounds of the present invention exhibit remarkable effects in organic electronic components.

[0344] These results show that even for compounds with similar molecular components, properties of the compounds such as hole characteristics, light-emitting efficiency characteristics, energy levels, hole injection and mobility characteristics, charge balance of holes and electrons, volume density, and intermolecular distance may be significantly different to a certain extent, making it difficult to predict based on the type and position of the substituted substituents, and the performance of the components can vary due to complex factors rather than a single structure affecting the overall device results.

[0345] Although the exemplary embodiments of the present invention have been described for illustrative purposes, those skilled in the art will understand that various modifications, additions, and substitutions are possible without departing from the scope and spirit of the present invention as disclosed in the appended claims. Therefore, the embodiments disclosed in the present invention are intended to illustrate the scope of the technical concept of the present invention, and the scope of the present invention is not limited by the embodiments. The scope of the present invention should be interpreted based on the appended claims and should be interpreted to include all technical concepts within the scope equivalent to the claims as belonging to the present invention.

[0346] [Description of Reference Numerals]

[0347] 100, 200, 300: Organic electronic components 110: First electrode

[0348] 120: Hole injection layer 130: Hole transport layer

[0349] 140: Light-emitting layer 150: Electron transport layer

[0350] 160: Electron injection layer 170: Second electrode

[0351] 180: Light efficiency enhancement layer 210: Buffer layer

[0352] 220: Light emission assisting layer 320: First hole injection layer

[0353] 330: First hole transport layer 340: First light-emitting layer

[0354] 350: First electron transport layer 360: First charge generation layer

[0355] 361: Second charge generation layer 420: Second hole injection layer

[0356] 430: Second hole transport layer 440: Second light-emitting layer

[0357] 450: Second electron transport layer CGL: Charge generation layer

[0358] ST1: First stack ST2: Second stack

Claims

1. A compound represented by any one of the following compounds P-5 to P-100:

2. A composition for an organic electronic element, comprising a compound represented by Formula 1 and a mixture of a compound represented by Formula: Formula 1 Formula 5 in: R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are the same as or different from each other and are each independently hydrogen or deuterium; *a is bonded to *b or *c, *d is bonded to *e or *f, a and e are independently integers from 0 to 5, b and f are independently integers from 0 to 4, c, d and g are independently integers from 0 to 3, L 15 Each is independently selected from: a single bond; C6-C 60 Arylene group; Fluorenylene group; C2-C ... 60 Heterocyclic groups; and C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused groups; Ar 15 Each independently selected from: C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused group; and -L'-N(R')(R"); Wherein L' is selected from: single bond; C6-C 60 Arylene group; Fluorenylene group; C2-C ... 60 Heterocyclic group; and C3-C 60 aliphatic ring; Wherein R' and R" are each independently selected from: C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic cyclic group; and C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused groups; Y 10 O, S, CR 51 R 52 or NR 53 , Ring B is C6-C 20 Aryl groups, R 31 and R 32 are the same or different and are independently selected from: hydrogen; deuterium; halogen; cyano group; nitro group; C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy groups; and C6-C 30 Aryloxy group; or multiple adjacent R 31 or multiple R 32 can be bonded to each other to form a ring, R 51 , R 52 and R 53 Each independently selected from: C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy groups; and C6-C 30 an aryloxy group; or, R 51 and R 52 may be bonded to each other to form a spiro ring, ba and bb are each independently an integer from 0 to 4, wherein the aryl group, the arylene group, the heterocyclic group, the fluorenyl group, the fluorenylene group, the condensed ring group, the aliphatic ring group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxy group and the aryloxy group may be substituted by one or more substituents selected from the group consisting of: deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 Alkylthio group; C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 20 Aryl group; C6-C substituted by deuterium 20 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl group; C7-C 20 Arylalkyl group; C8-C 20 arylalkenyl group; and -L'-N(R')(R"); in addition, the hydrogen of these substituents may be further replaced by one or more deuterium, and the substituents may be bonded to each other to form a saturated or unsaturated ring, wherein the term "ring" means a C3-C 60 Aliphatic ring or C6-C 60 Aromatic ring or C2-C 60 A heterocyclic group or a condensed ring formed by combining them. 3 . The composition for an organic electronic element according to claim 2 , wherein the composition is used as a host of a light emitting layer.

4. The composition for an organic electronic device according to claim 2, wherein Formula 1 comprises a compound selected from any one of Formulas 1-1 to 1-4: in, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , a, b, c, d, e, f and g are the same as defined in claim 2.

5. The composition for an organic electronic element according to claim 2, wherein the compound represented by Formula 1 may be any one of the following compounds P-1 to P-100:

6. The composition for an organic electronic element according to claim 2, wherein the compound represented by Formula 5 may be any one of the following compounds S-1 to S-116:

7. Organic electronic components, including: a first electrode; a second electrode; and an organic material layer formed between the first electrode and the second electrode; The organic material layer comprises the composition for an organic electronic element according to claim 2 or the compound according to claim 1 .

8. The organic electronic device according to claim 7, wherein: The organic electronic element further includes a light efficiency enhancing layer formed on at least one surface of the first electrode and the second electrode, the surface being opposite to the organic material layer. 9 . The organic electronic element according to claim 7 , wherein the organic material layer comprises two or more stacked bodies, the stacked body comprising a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the first electrode. 10 . The organic electronic element according to claim 9 , wherein the organic material layer further comprises a charge generation layer formed between the two or more stacked bodies. 11 . The organic electronic element according to claim 7 , wherein the organic material layer containing the compound according to claim 1 is a light emitting layer. 12 . An electronic device comprising a display device and a control unit for driving the display device, the display device comprising the organic electronic element according to claim 7 . 13 . The electronic device according to claim 12 , wherein the organic electronic element is at least one of an OLED, an organic solar cell, an organic photoconductor, an organic transistor, and an element for monochromatic or white lighting.

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