Composition for organic electroluminescent element and organic electroluminescent element comprising same

Abstract

The present invention relates to a composition for an organic electroluminescent element and an organic electroluminescent element comprising the same, the composition for an organic electroluminescent element comprising a first host represented by Chemical Formula 1 and a second host represented by Chemical Formula 2, the details of the Chemical Formulae 1 and 2 being the same as defined in the specification.

Description

Technical Field

[0001] The present invention relates to a composition for an organic electroluminescent element and an organic electroluminescent element comprising the same. Background Art

[0002] When a voltage is applied between two electrodes of an organic electroluminescent element (hereinafter referred to as an "organic EL element"), holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons transition to the ground state, light is emitted. At this time, the substances used for the organic layer can be divided into luminescent substances, hole injection substances, hole transport substances, electron transport substances, electron injection substances, etc. according to their functions.

[0003] The light-emitting layer forming materials of organic EL elements can be divided into blue, green and red light-emitting materials according to the light-emitting color. In addition, yellow and orange light-emitting materials are also used as light-emitting materials for presenting more natural colors. In addition, in order to increase the luminous efficiency by increasing the color purity and energy transfer, a host / dopant system can be used as a light-emitting material. Dopant substances can be divided into fluorescent dopants using organic substances and phosphorescent dopants using metal coordination compounds containing heavy atoms such as Ir and Pt. Since the development of such phosphorescent materials can theoretically increase the luminous efficiency by 4 times compared with fluorescence, not only phosphorescent dopants but also phosphorescent host materials have received attention.

[0004] So far, NPB, BCP, Alq3, etc. are widely known as hole injection layers, hole transport layers, hole blocking layers, and electron transport layers. Regarding luminescent materials, anthracene derivatives have been reported as fluorescent dopants / host materials. In particular, as phosphorescent materials with great advantages in improving efficiency among luminescent materials, metal coordination compounds containing Ir such as Firpic, Ir(ppy)3, (acac)Ir(btp)2, etc. have been used as blue, green, and red dopant materials. At present, CBP shows excellent characteristics as a phosphorescent host material.

[0005] However, although conventional organic layer materials have advantages in terms of light-emitting properties, they have low glass transition temperatures and very poor thermal stability, and therefore cannot achieve satisfactory lifespan in organic EL elements. Therefore, there is a demand for the development of organic layer materials with excellent performance. Summary of the invention

[0006] Technical issues

[0007] An object of the present invention is to provide a composition for an organic electroluminescent element that can achieve high efficiency and long life.

[0008] Another object of the present invention is to provide an organic electroluminescent element comprising the above composition as an organic layer material (eg, light-emitting layer material) and having low driving voltage, high light-emitting efficiency and improved life.

[0009] Solution to the problem

[0010] In order to achieve the above object, the present invention provides a composition for an organic electroluminescent element, which comprises a first host represented by the following chemical formula 1 and a second host represented by the following chemical formula 2:

[0011] [Chemical formula 1]

[0012]

[0013] [Chemical formula 2]

[0014]

[0015] (In the above chemical formulas 1 and 2,

[0016] D is deuterium,

[0017] a, d, f and h are integers from 0 to 3,

[0018] b, c, e, g and i are each an integer from 0 to 4,

[0019] j and k are each an integer from 0 to 5,

[0020] n1 is an integer from 1 to 5,

[0021] n2 is an integer of 0 or 1,

[0022] X1 is selected from the group consisting of O, S, Se, N(Ar3), C(Ar4)(Ar5) and Si(Ar6)(Ar7),

[0023] Y1 and Y2 are the same as or different from each other and are independently N or C(Ar8). In this case, at least one of Y1 and Y2 is N.

[0024] Ar1 to Ar8 and R1 to R5 are the same as or different from each other, and each independently can be selected from hydrogen, deuterium (D), halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, phosphine oxide, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 or they form a condensed ring with adjacent groups,

[0025] The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, alkylphosphine oxide, arylphosphine oxide, arylamine and condensed ring of Ar1 to Ar8 and R1 to R5 are each independently selected from deuterium, halogen, cyano, nitro, C2 to C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C1~C 40 Alkyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 The arylamine group is substituted or unsubstituted with one or more substituents; when there are multiple substituents, they are the same as or different from each other).

[0026] In addition, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers between the anode and the cathode, wherein the one or more organic layers comprise the composition.

[0027] Effects of the Invention

[0028] According to one embodiment of the present invention, by using a compound with strong hole characteristics and a compound with strong electron characteristics as the main body, an organic electroluminescent element can be realized that not only has low driving voltage, high efficiency and long life characteristics but also can exert excellent phosphorescent light-emitting characteristics.

[0029] The effects of the present invention are not limited to the above-exemplified contents, and this specification includes more various effects. BRIEF DESCRIPTION OF THE DRAWINGS

[0030] Figure 1 : is a cross-sectional view showing the structure of an organic electroluminescent element according to one embodiment of the present invention.

[0031] <Description of symbols>

[0032] 100: anode, 200: cathode,

[0033] 300: organic layer, 310: hole transport region,

[0034] 311: hole injection layer, 312: hole transport layer,

[0035] 320: light-emitting layer, 330: electron transport region,

[0036] 331: electron transport layer, 332: electron injection layer. DETAILED DESCRIPTION

[0037] The advantages and features of the present invention and methods for achieving them will become clear when referring to the embodiments described in detail in conjunction with the accompanying drawings. However, the present invention is not limited to the embodiments disclosed below and will be implemented in various forms different from each other. This embodiment is only provided to make the disclosure of the present invention complete and to fully inform the general technicians of the technical field to which the present invention belongs of the scope of the invention. The present invention is only defined by the scope of the claims. Therefore, in some embodiments, well-known process steps, well-known component structures, and well-known technologies are not specifically described to avoid the present invention being interpreted vaguely. Throughout the specification, the same figure numerals refer to the same constituent elements.

[0038] Unless otherwise defined, all terms (including technical and scientific terms) used in this specification may be used with the meanings that are generally understood by those skilled in the art to which the invention belongs. In addition, unless explicitly specifically defined, terms defined in generally used dictionaries should not be ideally or excessively interpreted.

[0039] Furthermore, throughout the specification, when it is stated that a certain part “comprises” a certain constituent element, unless there is a particular description to the contrary, it means that other constituent elements may also be included rather than being excluded.

[0040] In addition, throughout the specification, "above" or "upper" includes not only the case where it is located above or below the object part, but also the case where there are other parts in between, and does not necessarily mean that it is located on the upper side based on the direction of gravity.

[0041] In addition, in this specification, the terms “first”, “second”, etc. do not indicate any order or degree of importance, but are used to distinguish constituent elements from each other.

[0042] <Composition for organic electroluminescent element>

[0043] The composition for an organic electroluminescent element of the present invention is a composition for forming an organic layer (e.g., a light-emitting layer) of an organic electroluminescent element, and comprises a first main body represented by the above chemical formula 1 and a second main body represented by the above chemical formula 2. At this time, the above first main body is a compound having a structure in which three carbazoles are directly connected without a connecting group, and is a P-type main body with relatively strong hole characteristics. On the other hand, the above second main body is a compound having a structure in which a dibenzo part is combined with a phenyl part of a heterocyclic part containing 2,4,6-triphenyl-N through a connecting group, and is an N-type main body with relatively strong electronic characteristics. By using such a first main body and a second main body in combination, the composition of the present invention can realize an organic electroluminescent element with high efficiency and long life.

[0044] In the first main body represented by the above chemical formula 1, a, d and f are each an integer from 0 to 3, and b, c and e are each an integer from 0 to 4. Wherein, when a, b, c, d, e and f are each 0, it means that hydrogen is not replaced by deuterium, i.e., D. On the other hand, when a, d and f are each an integer from 1 to 3 and when b, c and e are each an integer from 1 to 4, it means that one or more hydrogens are replaced by deuterium (D). At this time, it can be 13≤a+b+c+d+e+f≤21. According to one example, the number of deuterium (D) contained in the above-mentioned first main body can be at least 13, specifically at least 21. Such a first main body can improve the stability of the chemical structure by deuterium (D) substitution, thereby simultaneously realizing the characteristics of the organic electroluminescent element, such as the low voltage, high efficiency and long life characteristics of the element.

[0045] Such deuterium may also be substituted by other substituents (R). In this case, when there are multiple other substituents (R), they may be the same or different from each other. The above other substituents (R) may be selected from halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, phosphine oxide, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 A group composed of arylamine groups.

[0046] In the first host represented by the above chemical formula 1, Ar1 and Ar2 are the same or different from each other, and each independently can be selected from hydrogen, deuterium (D), halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, phosphine oxide, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 Specifically, Ar1 and Ar2 are the same or different from each other and can be independently selected from C6 to C 60 The group consisting of an aryl group and a heteroaryl group having 5 to 60 atomic nuclei.

[0047] According to one example, Ar1 and Ar2 are the same as or different from each other, and each independently may be a substituent selected from the group consisting of the following substituents S1 to S4.

[0048]

[0049] In the above substituents S1 to S4, * is a site connecting to the above chemical formula 1.

[0050] According to Ar1 and Ar2, the first host represented by the above Chemical Formula 1 may be a compound represented by the following Chemical Formula 3, but is not limited thereto.

[0051] [Chemical formula 3]

[0052]

[0053] In the above chemical formula 3,

[0054] a, b, c, d, e and f are each the same as defined in the above Chemical Formula 1,

[0055] m1 and m2 are 0 or 1, respectively.

[0056] In addition, the first host represented by the above chemical formula 1 may have various structures depending on the connection positions between the carbazole moieties. According to one example, the first host represented by the above chemical formula 1 may be a compound represented by the following chemical formula 4.

[0057] [Chemical formula 4]

[0058]

[0059] In the above chemical formula 4,

[0060] a, b, c, d, e and f are each the same as defined in the above Chemical Formula 1,

[0061] m1 and m2 are 0 or 1, respectively.

[0062] Specifically, the first host represented by the above Chemical Formula 1 may be a compound represented by the following Chemical Formula 5.

[0063] [Chemical formula 5]

[0064]

[0065] In the above chemical formula 5,

[0066] a, b, c, d, e and f are each the same as defined in the above Chemical Formula 1,

[0067] m1 and m2 are 0 or 1, respectively.

[0068] The first host represented by the chemical formula 1 of the present invention described above can be further embodied as the following exemplary compounds, such as compounds A-1 to D-4, but is not limited thereto.

[0069]

[0070]

[0071] In the second host represented by the above Chemical Formula 2, Y1 and Y2 are the same as or different from each other and are independently N or C(Ar8), wherein at least one of Y1 and Y2 is N.

[0072] According to such Y1 and Y2, in the second host represented by the above chemical formula 2,

[0073] The moiety may be a moiety selected from the group consisting of the following moieties Mo-1 to Mo-3.

[0074]

[0075] In the above parts Mo-1 to Mo-3,

[0076] * is the site connected to the above chemical formula 2,

[0077] Y1 and Y2 are each independently C(Ar8),

[0078] Ar8 has the same meaning as in the above Chemical Formula 2.

[0079] In the second host represented by the above chemical formula 2, n1 is an integer from 1 to 5, and n2 is 0 or 1. According to one example, n1 can be 1 or 2, and n2 can be 0 or 1. In the above chemical formula 2, when n2 is 0, j is 1.

[0080] In the second host represented by the above chemical formula 2, X1 is selected from the group consisting of O, S, Se, N(Ar3), C(Ar4)(Ar5) and Si(Ar6)(Ar7). According to such X1, the dibenzo part can be a monovalent dibenzofuranyl, a monovalent dibenzothiophene group, a monovalent fluorenyl group, etc.

[0081] Ar3 to Ar8 are the same or different from each other and are independently selected from hydrogen, deuterium (D), halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, phosphine oxide, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60or they form a condensed ring with adjacent groups (e.g., Ar3-R1, Ar3-R2, Ar4-Ar5, Ar6-Ar7, Ar4-R1, Ar4-R2, Ar6-R1, Ar6-R2, etc.). Specifically, Ar3 to Ar8 are the same or different from each other and can be independently selected from C1 to C 40 Alkyl, C6~C 60 and a heteroaryl group with 5 to 60 atomic nuclei, or they form a condensed ring with adjacent groups (for example: Ar3-R1, Ar3-R2, Ar4-Ar5, Ar6-Ar7, Ar4-R1, Ar4-R2, Ar6-R1, Ar6-R2, etc.). The condensed ring can be selected from C3 to C 60 Condensed aliphatic ring (specifically C3~C 30 Condensed aliphatic ring), C6~C 60 Condensed aromatic ring (specifically C6~C 30 condensed aromatic ring), 5-membered to 60-membered condensed heteroaromatic ring (specifically 5-membered to 30-membered condensed heteroaromatic ring), C3-C 60 One or more of the group consisting of a spiro ring and combinations thereof.

[0082] According to one example, in the above chemical formula 2,

[0083] The moiety may be a moiety selected from the group consisting of the following moieties Dz-1 to Dz-32, but is not limited thereto.

[0084]

[0085]

[0086] In the above parts Dz-1 and Dz-32,

[0087] * is the site connected to the above chemical formula 2,

[0088] R1 can be C6~C 60 The aryl group may specifically be a phenyl group.

[0089] In the second host represented by the above chemical formula 2, h is an integer from 0 to 3, g and i are each an integer from 0 to 4, and j and k are each an integer from 0 to 5. When g, h, i, j and k are each 0, it means that hydrogen is not replaced by substituents R1 to R5. On the other hand, when h is an integer from 1 to 3, when g and i are each an integer from 1 to 4, and when j and k are each an integer from 1 to 5, one or more R1 to R5 are the same or different from each other, and each independently can be selected from deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, phosphine oxide, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 Specifically, one or more R1 to R5 are the same or different from each other, and each independently can be selected from hydrogen, halogen, cyano, nitro, amino, C1~C 40 Alkyl, C6~C 60 The group consisting of an aryl group and a heteroaryl group having 5 to 60 atomic nuclei.

[0090] The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, alkylphosphine oxide, arylphosphine oxide, arylamine and condensed ring of Ar3 to Ar8 and R1 to R5 can be independently selected from deuterium, halogen, cyano, nitro, C2 to C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C1~C 40 Alkyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 The arylamine group may be substituted or unsubstituted with one or more substituents in the group consisting of the arylamine group. At this time, when the substituents are multiple, they may be the same or different from each other.

[0091] The second host represented by the above Chemical Formula 2 may be a compound represented by the following Chemical Formula 6, but is not limited thereto.

[0092] [Chemical formula 6]

[0093]

[0094] In the above chemical formula 6,

[0095] i, j, k, R1, R3 to R5, n1, n2, X1, Y1 and Y2 are each the same as defined in the above Chemical Formula 2.

[0096] Specifically, the second host represented by the above Chemical Formula 2 may be a compound represented by the following Chemical Formula 7 or 8, but is not limited thereto.

[0097] [Chemical formula 7]

[0098]

[0099] [Chemical formula 8]

[0100]

[0101] In the above chemical formulas 7 and 8,

[0102] i, k, R1, R3, R5, n1, n2, Y1 and Y2 are each the same as defined in the above Chemical Formula 2, and X1 and X2 are each O or S, specifically O.

[0103] More specifically, the second host represented by the above Chemical Formula 2 may be a compound represented by the following Chemical Formula 9 or 10, but is not limited thereto.

[0104] [Chemical formula 9]

[0105]

[0106] [Chemical formula 10]

[0107]

[0108] In the above chemical formulas 9 and 10,

[0109] n1, n2, Y1 and Y2 are each the same as defined in Chemical Formula 2. Specifically, n1 may be 1 or 2, n2 may be 0 or 1, and Y1 and Y2 may both be N.

[0110] x and y are 0 or 1 respectively,

[0111] X1 and X2 are each O or S, specifically O,

[0112] D is deuterium,

[0113] o1 is an integer from 0 to 5,

[0114] o2 is an integer from 0 to 6,

[0115] o3 is an integer from 0 to 4,

[0116] o4 is an integer from 0 to 3,

[0117] o5 is an integer from 0 to 7.

[0118] The second host represented by the chemical formula 2 of the present invention described above can be further embodied as the following exemplary compounds, such as compounds E-1 to E-13, but is not limited thereto.

[0119]

[0120] In the present invention, "alkyl" means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, and hexyl.

[0121] In the present invention, "alkenyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

[0122] In the present invention, "alkynyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include ethynyl and 2-propynyl, but are not limited thereto.

[0123] In the present invention, "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine, but are not limited thereto.

[0124] In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having a nucleus number of 3 to 40, wherein one or more carbon atoms, preferably 1 to 3 carbon atoms, in the ring are substituted with heteroatoms such as N, O, S or Se. Examples of such heterocycloalkyl groups include morpholinyl and piperazinyl, but are not limited thereto.

[0125] In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms and composed of a single ring or a combination of two or more rings. In addition, it may also include a form in which two or more rings are simply attached (pendant) or condensed to each other. Examples of such aryl groups include phenyl, naphthyl, phenanthrenyl, anthracenyl, etc., but are not limited thereto.

[0126] In the present invention, "heteroaryl" means a monovalent substituent derived from a monocyclic heterocyclic or polycyclic aromatic hydrocarbon having an atomic nucleus number of 5 to 60. In this case, one or more carbons, preferably 1 to 3 carbons in the ring are substituted by heteroatoms such as N, O, S or Se. In addition, it may also include a form in which two or more rings are simply attached (pendant) or condensed to each other, and further may include a form condensed with an aryl group. Examples of such heteroaryl groups include six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridyl, 2-pyrimidinyl, etc., but are not limited thereto.

[0127] In the present invention, "alkoxy" is a monovalent substituent represented by R'O-, wherein R' means an alkyl group having 1 to 40 carbon atoms, and may include a linear, branched or cyclic structure. Examples of such alkoxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, tert-butoxy, n-butoxy, and pentyloxy.

[0128] In the present invention, "aryloxy" is a monovalent substituent represented by RO-, where R means an aryl group having 5 to 40 carbon atoms. Examples of such aryloxy groups include phenoxy, naphthoxy, diphenoxy and the like, but are not limited thereto.

[0129] In the present invention, "alkylsilyl" means a silyl group substituted with an alkyl group having 1 to 40 carbon atoms, including not only a monoalkylsilyl group but also a dialkylsilyl group and a trialkylsilyl group. In addition, "arylsilyl" means a silyl group substituted with an aryl group having 5 to 60 carbon atoms, including not only a monoarylsilyl group but also a diarylsilyl group, a triarylsilyl group and other polyarylsilyl groups.

[0130] In the present invention, the "alkylboryl group" means a boron group substituted by an alkyl group having 1 to 40 carbon atoms, and the "arylboryl group" means a boron group substituted by an aryl group having 6 to 60 carbon atoms.

[0131] In the present invention, "alkylphosphino" means a phosphino group substituted with an alkyl group having 1 to 40 carbon atoms, including not only a monoalkylphosphino group but also a dialkylphosphino group. In addition, in the present invention, "arylphosphino" means a phosphino group substituted with a monoaryl group or a diaryl group having 6 to 60 carbon atoms, including not only a monoarylphosphino group but also a diarylphosphino group.

[0132] In the present invention, the "arylamine group" means an amine group substituted with an aryl group having 6 to 60 carbon atoms, and includes not only a monoarylamine group but also a diarylamine group.

[0133] In the present invention, the "heteroarylamine group" means an amine group substituted with a heteroaryl group having 5 to 60 atomic nuclei, and includes not only a monoheteroarylamine group but also a diheteroarylamine group.

[0134] In the present invention, the (aryl)(heteroaryl)amine group means an amine group substituted with an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 5 to 60 atomic nuclei.

[0135] In the present invention, "condensed ring" means a condensed aliphatic ring having 3 to 40 carbon atoms, a condensed aromatic ring having 6 to 60 carbon atoms, a condensed aliphatic heterocyclic ring having 3 to 60 atomic nuclei, a condensed aromatic heterocyclic ring having 5 to 60 atomic nuclei, or a combination thereof.

[0136] The first body and the second body may be included in a weight ratio of 99:1 to 1:99. In this case, bipolar characteristics can be more effectively realized while improving efficiency and lifespan.

[0137] The composition of the present invention may further include a phosphorescent dopant. The phosphorescent dopant is a substance that is mixed in a trace amount in the first and second hosts to cause luminescence. As long as it is a substance known in the art, there is no particular limitation. As a non-limiting example, there are metal coordination compounds containing iridium (Ir) or platinum (Pt). Such a dopant can cause luminescence by multiple excitations (multiple excitations) that are excited to triplet states or above.

[0138] The dopant may be classified into a red dopant, a green dopant, and a blue dopant, and any red dopant, green dopant, and blue dopant generally known in the technical field may be used without particular limitation.

[0139] Specifically, non-limiting examples of red dopants include PtOEP (Pt(II)octaethylporphine), Ir(piq)3 (tris(2-phenylisoquinoline)iridium), Btp2Ir(acac) (bis(2-(2'-benzothienyl)-pyridinato-N,C3')iridium(acetylacetonate), or a mixture of two or more thereof.

[0140] In addition, non-limiting examples of green dopants include Ir(ppy)3(tris(2-phenylpyridine)iridium: tris(2-phenylpyridine)iridium), Ir(ppy)2(acac)(Bis(2-phenylpyridine)iridium,

[0141] (Acetylacetonato)iridium(III):bis(2-phenylpyridine)(acetylacetonato)iridium(III)), Ir(mppy)3(tris(2-(4-tolyl)phenylpiridine)iridium:tris(2-(4-tolyl)phenylpyridine)iridium), or a mixture of two or more thereof.

[0142] In addition, non-limiting examples of blue dopants include F2Irpic (Bis[3,5-difluoro-2-(2-pyridyl)phenyl](picolinato)iridium(III): bis[3,5-difluoro-2-(2-pyridyl)phenyl(picolinato)iridium(III)), (F2ppy)2Ir(tmd), Ir(dfppz)3, or a mixture of two or more thereof.

[0143] The content of the dopant is not particularly limited. For example, based on the total amount of the composition, it can be about 0 to 10 wt %, specifically about 0.1 to 10 wt %, and more specifically about 1 to 30 wt %.

[0144] <Organic electroluminescent element>

[0145] The organic electroluminescent element of one embodiment of the present invention comprises an anode, a cathode and one or more organic layers between the anode and the cathode, wherein the organic layers comprise the composition. According to one example, the organic layers may comprise a light-emitting layer, and the composition may be included as the main body of the light-emitting layer. Thus, the organic electroluminescent element of the present invention can not only have low driving voltage, high efficiency and long life characteristics, but also can exert excellent phosphorescent light-emitting characteristics.

[0146] Hereinafter, preferred embodiments of the organic electroluminescent element of the present invention will be described with reference to the accompanying drawings. However, the embodiments of the present invention can be deformed into various other forms, and the scope of the present invention is not limited by the embodiments described below. In order to avoid repetition, the description of the constituent elements described in the above-mentioned organic electroluminescent element composition will be omitted.

[0147] Figure 1 This is a cross-sectional view schematically showing the structure of an organic electroluminescent element according to one embodiment of the present invention.

[0148] Reference Figure 1 To illustrate, an organic electroluminescent element of an embodiment of the present invention may include an anode 100 disposed on a substrate (not shown), a cathode 200 disposed opposite to the anode, and one or more organic layers 300 between the anode 100 and the cathode 200, wherein the one or more organic layers 300 may include a hole transport region 310, a light-emitting layer 320, and an electron transport region 330. At this time, the light-emitting layer 320 may include the above-mentioned composition as a main body. Optionally, the organic electroluminescent element of the present invention may also include a covering layer (not shown) disposed on the cathode 200.

[0149] Hereinafter, each structure of the organic electroluminescent element of the present invention will be described in detail.

[0150] (1) Anode

[0151] In the organic electroluminescent element of the present invention, the anode 100 is mainly arranged on the substrate, and can be electrically connected to the driving thin film transistor to receive the driving current from the driving thin film transistor. Such anode 100 is formed of a material with a high work function, so it will inject holes into the organic layer 300, that is, the hole transport region 310 [for example: hole injection layer 311].

[0152] The material forming such an anode is not particularly limited, and common materials known in the art can be used. For example, there are metals such as vanadium, chromium, copper, zinc, and gold; their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al and SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline; and carbon black, but are not limited thereto.

[0153] The method for manufacturing the above-mentioned anode is not particularly limited, and can be manufactured by a common method known in the art. For example, the above-mentioned anode material can be coated on a substrate to form by a known thin film forming method such as sputtering, ion plating, vacuum evaporation, spin coating, etc.

[0154] The substrate is a plate-shaped member that supports the organic electroluminescent element, and examples thereof include, but are not limited to, a silicon wafer, quartz, a glass plate, a metal plate, a clinker film, and a sheet.

[0155] (2) Cathode

[0156] In the organic electroluminescent element of the present invention, the cathode 200 is an electrode disposed opposite to the anode, and specifically, is disposed on the electron transport region 330. Such a cathode 200 is composed of a material with a low work function, and thus injects electrons into the adjacent organic layer, that is, the electron transport region 330 [for example, the electron injection layer 332].

[0157] The material forming such a cathode is not particularly limited, and common materials known in the art can be used, such as metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin, and lead; alloys thereof; and multilayer structure materials such as LiF / Al and LiO2 / Al, but are not limited thereto.

[0158] The method for manufacturing the cathode is not particularly limited, and like the anode, it can be manufactured by a common method known in the art. For example, the cathode material can be coated on one or more organic layers 300 described below, specifically on the electron transport region, such as the electron injection layer 332, by the thin film forming method described above.

[0159] (3) Organic layer

[0160] In the organic electroluminescent element of the present invention, the one or more organic layers 300 are disposed between the anode 100 and the cathode 200 , and include a hole transport region 310 , a light emitting layer 320 , and an electron transport region 330 .

[0161] According to one example, Figure 1 As shown, the one or more organic layers 300 may include a hole injection layer 311 , a hole transport layer 312 , a light emitting layer 320 , an electron transport layer 331 and an electron injection layer 332 which are sequentially arranged on the anode 100 .

[0162] Hereinafter, each organic layer will be described.

[0163] 1) Hole transport region

[0164] In the organic electroluminescent element 100 of the present invention, the hole transport region 310 is a part of the organic layer 300 disposed on the anode 100 , and plays a role in transferring holes (holes) injected from the anode 100 to the adjacent light-emitting layer 320 .

[0165] Such a hole transport region 310 may include one or more selected from the group consisting of a hole injection layer 311 and a hole transport layer 312. At this time, when considering the characteristics of the organic electroluminescent element, it is preferred to include both the hole injection layer 311 and the hole transport layer 312. As an example, the hole transport region 310 is as follows: Figure 1 The anode 100 may include a hole injection layer 311 and a hole transport layer 312 sequentially stacked on the anode 100 .

[0166] The material forming the hole injection layer 311 and the hole transport layer 312 of the present invention is not particularly limited as long as it is a material with low hole injection barrier and high hole mobility, and the hole injection layer / transport layer material used in the art can be used. At this time, the materials forming the hole injection layer 311 and the hole transport layer 312 can be the same or different from each other.

[0167] Specifically, the hole injection layer 311 includes a hole injection substance known in the art. Non-limiting examples of the hole injection substance include phthalocyanine compounds such as copper phthalocyanine, N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolylamino)phenyl]-biphenyl-4,4'-diamine (DNTPD), 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(N,N-di ... -Tris(N,N-diphenylamino)triphenylamine, TDATA), 4,4',4"-tris{N,-(2-naphthyl)-N-phenylamino}-triphenylamine, 2TNATA), Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate, PEDOT / PSS), Polyaniline / Dodecylbenzenesulfonic acid acid, PANI / DBSA), polyaniline / camphor sulfonic acid (Polyaniline / Camphor sulfonic acid, PANI / CSA), (Polyaniline) / poly(4-styrenesulfonate), (Polyaniline) / poly(4-styrenesulfonate), PANI / PSS, etc., which can be used alone or in combination of two or more.

[0168] The hole transport layer 312 includes hole transport materials known in the art. Non-limiting examples of the hole transport materials include carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole; fluorene derivatives; amine derivatives; N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), 4,4',4"-tri(N-carbazole) and 4,4',4"-tri(N-carbazole). Triphenylamine derivatives such as 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB), 4,4'-cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine] (TAPC), etc., can be used alone or in combination of two or more.

[0169] The hole transport region 310 can be manufactured by a common method known in the art, such as vacuum evaporation, spin coating, casting, Langmuir-Blodgett (LB), inkjet printing, laser printing, laser induced thermal imaging (LITI), etc., but not limited thereto.

[0170] 2) Luminescent layer

[0171] In the organic electroluminescent element of the present invention, the light-emitting layer 320 is a part of the organic layer 300 between the anode 100 and the cathode 200, and is specifically disposed on the hole transport region 320. Figure 1 As shown, the light emitting layer 320 may be disposed on the hole transport layer 312 .

[0172] Such a light-emitting layer 320 is a layer where holes and electrons injected from the anode and the cathode are combined to form excitons. Depending on the material forming the light-emitting layer 320, the color of light emitted by the organic electroluminescent element can be changed.

[0173] The light-emitting layer 320 of the present invention comprises the composition comprising the first host represented by the above chemical formula 1 and the second host represented by the above chemical formula 2. The above composition may further selectively contain a phosphorescent dopant. By including the above composition as the light-emitting layer 320 material, the organic electroluminescent element of the present invention can not only have low driving voltage, high efficiency and long life characteristics, but also can exert excellent phosphorescent luminescence characteristics.

[0174] The light emitting layer 320 of the present invention may be a red light emitting layer including a red phosphorescent material, a green light emitting layer including a green phosphorescent material, or a blue light emitting layer including a blue phosphorescent material. According to one example, it may be a light emitting layer including a green phosphorescent material.

[0175] The above-mentioned light-emitting layer 320 can be constituted as: a single layer composed of one substance; a single layer composed of multiple substances different from each other; or a multilayer of two or more layers each composed of different substances. Among them, in the case where the light-emitting layer 320 is a plurality of layers, the organic electroluminescent element can emit light of multiple colors. Specifically, the present invention can provide an organic electroluminescent element that presents mixed colors by arranging a plurality of light-emitting layers composed of heterogeneous materials in series. In addition, in the case of including a plurality of light-emitting layers, the driving voltage of the element increases, while the current value in the organic electroluminescent element remains constant, thereby being able to provide an organic electroluminescent element having a luminous efficiency corresponding to the number of light-emitting layers.

[0176] Although not shown in the drawings, the organic electroluminescent device of the present invention may include a plurality of light-emitting stacks (not shown) including at least one light-emitting layer.

[0177] The multiple light-emitting layers included in such a light-emitting stack can be light-emitting layers that emit light of different colors from each other or light-emitting layers that emit light of the same color. That is, the light-emitting color can change depending on the material constituting the light-emitting layer. As an example, multiple light-emitting stacks can include materials that emit blue, green, red, yellow, white, etc. light, and can be formed using phosphorescent or fluorescent materials. At this time, the colors displayed by each light-emitting layer can be complementary to each other. In addition, colors can also be selected according to color combinations that can emit white light. Each of these light-emitting layers can respectively contain a phosphorescent dopant or a fluorescent dopant corresponding to the selected color.

[0178] Although not shown in the drawings, the organic electroluminescent element of the present invention may further include a charge generation layer (CGL) (not shown) disposed between adjacent stacks among the plurality of light emitting stacks to connect them.

[0179] A charge generation layer (CGL) refers to a layer that separates adjacent light-emitting stacks in an organic electroluminescent element having multiple light-emitting stacks and is not in direct contact with two electrodes (e.g., anode and cathode). Such a charge generation layer is disposed between two light-emitting stacks adjacent to each other, and acts as a cathode (cathode) that generates electrons and provides electrons to one light-emitting stack, and acts as an anode (anode) that generates holes and provides holes to the other light-emitting stack. For such a charge generation layer, any substance that is known in the art as a charge generation layer material can be used without restriction. In addition, the substance used for the above-mentioned charge generation layer can be formed by doping with common n-type substances and / or p-type substances that are known in the art.

[0180] The light-emitting layer 320 can be manufactured by a common method known in the art. For example, there are vacuum evaporation, spin coating, casting, Langmuir-Blodgett (LB), inkjet printing, laser printing, laser induced thermal imaging (LITI), etc., but not limited to these. As an example, the light-emitting layer can be formed by co-depositing the first host represented by the above chemical formula 1 and the second host represented by the above chemical formula 2. At this time, the dopant can also be co-deposited together.

[0181] 3) Electron transport region

[0182] In the organic electroluminescent element of the present invention, the electron transport region 330 is an organic layer disposed on the light-emitting layer 320 , and allows electrons injected from the cathode 200 to migrate to the light-emitting layer 320 .

[0183] Such an electron transport region 330 may include one or more selected from the group consisting of an electron transport layer 331 and an electron injection layer 332 .

[0184] As an example, the electron transport region 330 is Figure 1 The structure shown may include an electron transport layer 331 and an electron injection layer 332 which are sequentially stacked on the light emitting layer 320 .

[0185] In the electron transport region 330 of the present invention, for the electron transport layer 331, any electron transport material that is easy to inject electrons and has a large electron mobility can be used without restriction. Non-limiting examples of such electron transport materials include oxazole compounds, isoxazole compounds, triazole compounds, isothiazole compounds, oxadiazole compounds, thiadiazole compounds, perylene compounds, aluminum complexes [e.g., Alq3 (tris(8-quinolinolato)-aluminum), BAlq, SAlq, Alph3, Almq3], gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc., which can be used alone or in combination of two or more.

[0186] In addition, the electron injection layer 332 can use an electron injection material that is easy to inject electrons and has a high electron mobility without limitation. Non-limiting examples of the above-mentioned electron injection material include LiF, Li2O, BaO, NaCl, CsF; lanthanum metals such as Yb; or halogenated metals such as RbCl, RbI, etc., which can be used alone or in combination of two or more.

[0187] The electron transport region 330 of the present invention, specifically, the electron transport layer 331 and / or the electron injection layer 332 may also use a material co-evaporated with an n-type dopant to facilitate electron injection from the cathode 200. At this time, the n-type dopant may be an alkali metal coordination compound known in the art without limitation, and as an example, alkali metals, alkaline earth metals, or rare earth metals may be cited.

[0188] The electron transport region 330 can be manufactured by a common method known in the art, such as vacuum evaporation, spin coating, casting, Langmuir-Blodgett (LB), inkjet printing, laser printing, laser induced thermal imaging (LITI), etc., but not limited thereto.

[0189] 4) Luminescent auxiliary layer

[0190] Although not shown in the figure, the organic electroluminescent element of the present invention may further include a light-emitting auxiliary layer disposed between the hole transport region 310 and the light-emitting layer 320 .

[0191] The light-emitting auxiliary layer plays a role in transferring holes migrated from the hole transport region 310 to the light-emitting layer 320 or blocking the migration of electrons and / or excitons while adjusting the thickness of the organic layer 300. In particular, the light-emitting auxiliary layer has a high LUMO value to prevent electrons from migrating to the hole transport layer 312, and has a high triplet energy to prevent the excitons of the light-emitting layer 320 from diffusing to the hole transport layer 312.

[0192] Such a light-emitting auxiliary layer may contain a hole transporting substance and may be made of the same substance as the hole transporting region. In addition, the light-emitting auxiliary layers of the red, green and blue organic electroluminescent elements may be made of the same material.

[0193] There are no particular restrictions on the materials of the light-emitting auxiliary layer, for example, there are carbazole derivatives, arylamine derivatives, etc. Specifically, as examples of the light-emitting auxiliary layer, there are N,N-dinaphthyl-N,N'-diphenyl benzidine (NPD), N,N'-bis-(3-methylphenyl)-N,N'-bis(phenyl)-benzidine (TPD), s-TAD, 4,4',4-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (MTDATA), etc., but not limited to these. They can be used alone or in combination of two or more.

[0194] In addition, in addition to the above-mentioned substances, the above-mentioned light-emitting auxiliary layer may also contain a p-type dopant. As the p-type dopant that can be used in the present invention, as long as it is a known p-type dopant commonly used in the technical field, it can be used without special restrictions. At this time, the content of the p-type dopant can be appropriately adjusted within the range known in the technical field, for example, based on 100 parts by weight of the hole transport substance, it can be about 0.5 to 50 parts by weight.

[0195] The above-mentioned light-emitting auxiliary layer can be formed by vacuum evaporation, spin coating, casting, Langmuir-Blodgett (LB), inkjet printing, laser printing, laser thermal transfer (Laser Induced Thermal Imaging, LITI), etc. as known in the technical field, but is not limited to these.

[0196] 5) Hole blocking layer

[0197] Although not shown in the figure, the organic electroluminescent element 100 of the present invention may further include a hole blocking layer disposed between the light-emitting layer 320 and the electron transporting region 330 .

[0198] The hole blocking layer 333 can prevent excitons or holes generated in the light-emitting layer 320 from diffusing (migrating) to the electron transport layer 331 , thereby improving the life of the organic electroluminescent element.

[0199] For the material of such a hole blocking layer, any material with common electron transport properties known in the art can be used without limitation, for example, it can be 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), bis(2-methyl-8-quinolinolato)(4-phenyl-phenolato)aluminum, etc.

[0200] The hole blocking layer can be formed by vacuum evaporation, spin coating, casting, Langmuir-Blodgett (LB), inkjet printing, laser printing, laser induced thermal imaging (LITI), etc. as known in the technical field, but is not limited thereto.

[0201] (4) Covering layer

[0202] Optionally, the organic electroluminescent element 100 of the present invention may further include a covering layer (not shown) disposed on the cathode 200 .

[0203] The cover layer protects the organic electroluminescent element and helps the light generated in the organic layer to be effectively emitted to the outside.

[0204] The above-mentioned covering layer may include one or more selected from the group consisting of tri-8-hydroxyquinoline aluminum (Alq3), ZnSe, 2,5-bis(6'-(2',2""-bipyridine))-1,1-dimethyl-3,4-diphenylsilole, 4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (α-NPD), N,N''-diphenyl-N,N''-bis(3-methylphenyl)-1,1''-biphenyl-4,4''-diamine (TPD), and 1,1''-bis(di-4-tolylaminophenyl)cyclohexane (TAPC). The material forming such a covering layer is inexpensive compared to the materials of other layers of the organic electroluminescent element.

[0205] Such a cover layer may be a single layer, but may include two or more layers having mutually different refractive indexes so that the refractive index gradually changes while passing through the two or more layers.

[0206] The cover layer can be produced by a common method known in the art. For example, various methods such as vacuum deposition, spin coating, casting, or Langmuir-Blodgett (LB) method can be used.

[0207] The organic electroluminescent element of the present invention has a structure in which an anode 100, an organic layer 300 and a cathode 200 are stacked in sequence. Depending on the situation, an insulating layer (not shown) or an adhesive layer (not shown) arranged between the anode 100 and the organic layer 300 or between the cathode 200 and the organic layer 300 may also be included. Such an organic electroluminescent element of the present invention maintains maximum luminous efficiency when voltage and current are applied, and the half-life of the initial brightness is increased, so that the life characteristics are excellent.

[0208] The organic electroluminescent element of the present invention can be manufactured according to the usual methods known in the art. As an example, the organic electroluminescent element can be manufactured by vacuum evaporating an anode material on a substrate, and then vacuum evaporating hole transport region material, luminescent layer material, electron transport region material and cathode material on the anode in sequence.

[0209] Hereinafter, the present invention will be described in detail by way of examples, which are as follows. However, the following examples are merely illustrative of the present invention, and the present invention is not limited to the following examples.

[0210] <Preparation Example 1-1> Synthesis of Cz-D1

[0211]

[0212] Under a nitrogen flow, 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7 (134.3 g, 530.6 mmol), iodobenzene (130.0 g, 636.7 mmol), Cu (16.8 g, 265.3 mmol), K2CO3 (146.7 g, 1,061.3 mmol) and toluene (1000 ml) were mixed and stirred at 110°C for 12 hours.

[0213] After the reaction, the product was extracted with ethyl acetate, and then water was removed with MgSO 4 . The product was purified by column chromatography (hexane:EA=5:1 (v / v)) to obtain Cz-D1 (125.7 g, yield 72%).

[0214] Mass (theoretical value: 329.25, measured value: 329 g / mol)

[0215] <Preparation Example 1-2> Synthesis of Cz-D2

[0216]

[0217] The same process as Preparation Example 1-1 was carried out except that 4-iodo-1,1′-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene used in Preparation Example 1-1, thereby obtaining the target compound Cz-D2 (135.5 g, yield 63%).

[0218] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0219] <Preparation Example 1-3> Synthesis of Cz-D3

[0220]

[0221] The target compound Cz-D3 (148.4 g, yield 69%) was obtained by the same process as in Preparation Example 1-1 except that 3-iodo-1,1′-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene used in Preparation Example 1-1.

[0222] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0223] <Preparation Example 1-4> Synthesis of Cz-D4

[0224]

[0225] The same process as Preparation Example 1-1 was carried out except that 2-iodo-1,1′-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene used in Preparation Example 1-1, thereby obtaining the target compound Cz-D4 (96.8 g, yield 45%).

[0226] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0227] <Preparation Example 2-1> Synthesis of Cz-D5

[0228]

[0229] The target compound Cz-D5 (117.1 g, yield 67%) was obtained by carrying out the same process as Preparation Example 1-1, except that 4-bromo-9H-carbazole-1,2,3,5,6,7,8-d7 (134.3 g, 530.6 mmol) was used instead of 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7 used in Preparation Example 1-1.

[0230] Mass (theoretical value: 329.25, measured value: 329 g / mol)

[0231] <Preparation Example 2-2> Synthesis of Cz-D6

[0232]

[0233] The target compound Cz-D6 (139.8 g, yield 65%) was obtained by the same process as in Preparation Example 2-1 except that 4-iodo-1,1′-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene used in Preparation Example 2-1.

[0234] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0235] <Preparation Example 2-3> Synthesis of Cz-D7

[0236]

[0237] The target compound Cz-D7 (152.7 g, yield 71%) was obtained by the same process as in Preparation Example 2-1 except that 3-iodo-1,1′-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene used in Preparation Example 2-1.

[0238] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0239] <Preparation Example 2-4> Synthesis of Cz-D8

[0240]

[0241] The same process as in Preparation Example 2-1 was carried out except that 2-iodo-1,1′-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene, thereby obtaining the target compound Cz-D8 (75.2 g, yield 35%).

[0242] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0243] <Preparation Example 3-1> Synthesis of Cz-D9

[0244]

[0245] The target compound Cz-D9 (134.5 g, yield 77%) was obtained by carrying out the same process as Preparation Example 1-1, except that 2-bromo-9H-carbazole-1,3,4,5,6,7,8-d7 (134.3 g, 530.6 mmol) was used instead of 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7 used in Preparation Example 1-1.

[0246] Mass (theoretical value: 329.25, measured value: 329 g / mol)

[0247] <Preparation Example 3-2> Synthesis of Cz-D10

[0248]

[0249] The same process as in Preparation Example 3-1 was carried out except that 4-iodo-1,1′-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene used in Preparation Example 3-1, thereby obtaining the target compound Cz-D10 (159.1 g, yield 74%).

[0250] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0251] <Preparation Example 3-3> Synthesis of Cz-D11

[0252]

[0253] The same procedure as in Preparation Example 3-1 was carried out except that 3-iodo-1,1′-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene to obtain the target compound Cz-D11 (163.4 g, yield 76%).

[0254] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0255] <Preparation Example 3-4> Synthesis of Cz-D12

[0256]

[0257] The target compound Cz-D12 (92.4 g, yield 43%) was obtained by the same process as in Preparation Example 3-1 except that 2-iodo-1,1′-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene used in Preparation Example 3-1.

[0258] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0259] <Preparation Example 4-1> Synthesis of Cz-D13

[0260]

[0261] The target compound Cz-D13 (94.3 g, yield 54%) was obtained by carrying out the same process as Preparation Example 1-1, except that 1-bromo-9H-carbazole-2,3,4,5,6,7,8-d7 (134.3 g, 530.6 mmol) was used instead of 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7 used in Preparation Example 1-1.

[0262] Mass (theoretical value: 329.25, measured value: 329 g / mol)

[0263] <Preparation Example 4-2> Synthesis of Cz-D14

[0264]

[0265] The same process as in Preparation Example 4-1 was carried out except that 4-iodo-1,1′-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene, thereby obtaining the target compound Cz-D14 (122.6 g, yield 57%).

[0266] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0267] <Preparation Example 4-3> Synthesis of Cz-D15

[0268]

[0269] The same process as in Preparation Example 4-1 was carried out except that 3-iodo-1,1′-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene used in Preparation Example 4-1, thereby obtaining the target compound Cz-D15 (111.8 g, yield 52%).

[0270] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0271] <Preparation Example 4-4> Synthesis of Cz-D16

[0272]

[0273] The same process as in Preparation Example 4-1 was carried out except that 2-iodo-1,1′-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene, thereby obtaining the target compound Cz-D16 (68.8 g, yield 32%).

[0274] Mass (theoretical value: 405.35, measured value: 405 g / mol)

[0275] <Preparation Example 5-1> Synthesis of BCz-D1

[0276] <Step 1> 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1, Synthesis of 2,4,5,6,7,8-d7

[0277]

[0278] Under a nitrogen flow, Cz-D1 (100.0 g, 303.7 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (84.8 g, 334.1 mmol), Pd(dppf)Cl2 (26.6 g, 30.3 mmol), KOAc (85.8 g, 911.1 mmol) and 1,4-dioxane (1000 ml) were mixed and stirred at 130°C for 12 hours.

[0279] After the reaction, extraction was performed with ethyl acetate, water was removed with MgSO4, and purification was performed with column chromatography (hexane:EA=8:1 (v / v)) to obtain 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7 (96.0 g, yield 84%).

[0280] Mass (theoretical value: 376.3, measured value: 376 g / mol)

[0281] <Step 2> Synthesis of BCz-D1

[0282]

[0283] Under a nitrogen flow, 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7 (96.0 g, 255.1 mmol), 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7 (77.5 g, 306.1 mmol), Pd(PPh3)4 (14.7 g, 12.7 mmol), K2CO3 (88.1 g, 637.8 mmol) and 1,4-dioxane / H2O (1000 ml / 250 ml) were stirred at 120°C for 4 hours.

[0284] After the reaction was completed, the mixture was extracted with dichloromethane, and then MgSO4 was added and filtered. The solvent was removed from the obtained organic layer, and then the mixture was purified by column chromatography (hexane:EA=7:1 (v / v)) to obtain BCz-D1 (71.1 g, yield 66%).

[0285] Mass (theoretical value: 422.59, measured value: 422 g / mol)

[0286] <Preparation Example 5-2> Synthesis of BCz-D2

[0287]

[0288] The same process as in Preparation Example 5-1 was carried out except that Cz-D2 (100 g, 246.7 mmol) obtained in Preparation Example 1-2 was used instead of Cz-D1 used in Preparation Example 5-1, thereby obtaining the target compound BCz-D2 (66.4 g, final yield 54.0%).

[0289] Mass (theoretical value: 498.69, measured value: 498 g / mol)

[0290] <Preparation Example 5-3> Synthesis of BCz-D3

[0291]

[0292] The same process as in Preparation Example 5-1 was carried out except that Cz-D3 (100 g, 246.7 mmol) obtained in Preparation Example 1-3 was used instead of Cz-D1 used in Preparation Example 5-1, thereby obtaining the target compound BCz-D3 (59.7 g, final yield 48.5%).

[0293] Mass (theoretical value: 498.69, measured value: 498 g / mol)

[0294] <Preparation Example 5-4> Synthesis of BCz-D4

[0295]

[0296] The same process as in Preparation Example 5-1 was carried out except that Cz-D4 (100 g, 246.7 mmol) obtained in Preparation Example 1-4 was used instead of Cz-D1 used in Preparation Example 5-1, thereby obtaining the target compound BCz-D4 (59.4 g, final yield 48.3%).

[0297] Mass (theoretical value: 498.69, measured value: 498 g / mol)

[0298] [Synthesis Example 1] Synthesis of A-1

[0299]

[0300] Under nitrogen flow, BCz-D1 (10.0 g, 23.6 mmol) obtained in Preparation Example 5-1, Cz-D1 (9.3 g, 28.3 mmol) obtained in Preparation Example 1-1, Pd(OAc)2 (1.36 g, 1.18 mmol), P(t-Bu)3 (0.57 ml, 2.36 mmol), NaO(t-Bu) (4.55 g, 47.3 mmol) and toluene (100 ml) were mixed and stirred at 110°C for 5 hours. After the reaction, toluene was concentrated, and the solid salt was filtered and purified by recrystallization to obtain the target compound A-1 (13.0 g, yield 82%).

[0301] Mass (theoretical value: 670.93, measured value: 670 g / mol)

[0302] [Synthesis Example 2] Synthesis of A-2

[0303]

[0304] The same process as in Synthesis Example 1 was carried out except that Cz-D2 (10.0 g, 23.6 mmol) obtained in Preparation Example 1-2 was used instead of Cz-D1 used in Synthesis Example 1, thereby obtaining the target compound A-2 (13.8 g, yield 78%).

[0305] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0306] [Synthesis Example 3] Synthesis of A-3

[0307]

[0308] The same process as Synthesis Example 1 was carried out except that Cz-D3 (10.0 g, 23.6 mmol) obtained in Preparation Example 1-3 was used instead of Cz-D1 used in Synthesis Example 1, thereby obtaining the target compound A-3 (13.2 g, yield 75%).

[0309] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0310] [Synthesis Example 4] Synthesis of A-4

[0311]

[0312] The same process as Synthesis Example 1 was carried out except that Cz-D4 (10.0 g, 23.6 mmol) obtained in Preparation Example 1-4 was used instead of Cz-D1 used in Synthesis Example 1, thereby obtaining the target compound A-4 (12.2 g, yield 69%).

[0313] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0314] [Synthesis Example 5] Synthesis of A-5

[0315]

[0316] The same process as Synthesis Example 1 was carried out except that Cz-D5 (9.3 g, 23.6 mmol) obtained in Preparation Example 2-1 was used instead of Cz-D1 used in Synthesis Example 1, thereby obtaining the target compound A-5 (8.73 g, yield 55%).

[0317] Mass (theoretical value: 670.93, measured value: 670 g / mol)

[0318] [Synthesis Example 6] Synthesis of A-6

[0319]

[0320] The same process as Synthesis Example 1 was carried out except that Cz-D6 (10.0 g, 23.6 mmol) obtained in Preparation Example 2-2 was used instead of Cz-D1 used in Synthesis Example 1, thereby obtaining the target compound A-6 (7.42 g, yield 42%).

[0321] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0322] [Synthesis Example 7] Synthesis of A-7

[0323]

[0324] The same process as Synthesis Example 1 was carried out except that Cz-D7 (10.0 g, 23.6 mmol) obtained in Preparation Example 2-3 was used instead of Cz-D1 used in Synthesis Example 1, thereby obtaining the target compound A-7 (8.83 g, yield 50%).

[0325] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0326] [Synthesis Example 8] Synthesis of A-8

[0327]

[0328] The same process as Synthesis Example 1 was carried out except that Cz-D8 (10.0 g, 23.6 mmol) obtained in Preparation Example 2-4 was used instead of Cz-D1 used in Synthesis Example 1, thereby obtaining the target compound A-8 (9.89 g, yield 56%).

[0329] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0330] [Synthesis Example 9] Synthesis of A-9

[0331]

[0332] The same process as Synthesis Example 1 was carried out except that Cz-D9 (9.3 g, 23.6 mmol) obtained in Preparation Example 3-1 was used instead of Cz-D1 used in Synthesis Example 1, thereby obtaining the target compound A-9 (8.41 g, yield 53%).

[0333] Mass (theoretical value: 670.93, measured value: 670 g / mol)

[0334] [Synthesis Example 10] Synthesis of A-10

[0335]

[0336] The same process as Synthesis Example 1 was carried out except that Cz-D10 (10.0 g, 23.6 mmol) obtained in Preparation Example 3-2 was used instead of Cz-D1 used in Synthesis Example 1, thereby obtaining the target compound A-10 (8.66 g, yield 49%).

[0337] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0338] [Synthesis Example 11] Synthesis of A-11

[0339]

[0340] The same process as Synthesis Example 1 was carried out except that Cz-D11 (10.0 g, 23.6 mmol) obtained in Preparation Example 3-3 was used instead of Cz-D1 used in Synthesis Example 1, thereby obtaining the target compound A-11 (9.01 g, yield 51%).

[0341] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0342] [Synthesis Example 12] Synthesis of A-12

[0343]

[0344] The same process as Synthesis Example 1 was carried out except that Cz-D12 (10.0 g, 23.6 mmol) obtained in Preparation Example 3-4 was used instead of Cz-D1 used in Synthesis Example 1, thereby obtaining the target compound A-12 (9.19 g, yield 52%).

[0345] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0346] [Synthesis Example 13] Synthesis of A-13

[0347]

[0348] The same process as Synthesis Example 1 was carried out except that Cz-D13 (9.3 g, 23.6 mmol) obtained in Preparation Example 4-1 was used instead of Cz-D1 used in Synthesis Example 1, thereby obtaining the target compound A-13 (9.52 g, yield 60%).

[0349] Mass (theoretical value: 670.93, measured value: 670 g / mol)

[0350] [Synthesis Example 14] Synthesis of A-14

[0351]

[0352] The same process as Synthesis Example 1 was carried out except that Cz-D14 (10.0 g, 23.6 mmol) obtained in Preparation Example 4-2 was used instead of Cz-D1 used in Synthesis Example 1, thereby obtaining the target compound A-14 (10.78 g, yield 61%).

[0353] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0354] [Synthesis Example 15] Synthesis of A-15

[0355]

[0356] The same process as Synthesis Example 1 was carried out except that Cz-D15 (10.0 g, 23.6 mmol) obtained in Preparation Example 4-3 was used instead of Cz-D1 used in Synthesis Example 1, thereby obtaining the target compound A-15 (11.13 g, yield 63%).

[0357] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0358] [Synthesis Example 16] Synthesis of A-16

[0359]

[0360] The same process as Synthesis Example 1 was carried out except that Cz-D16 (10.0 g, 23.6 mmol) obtained in Preparation Example 4-4 was used instead of Cz-D1 used in Synthesis Example 1, thereby obtaining the target compound A-16 (9.02 g, yield 51%).

[0361] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0362] [Synthesis Example 17] Synthesis of B-1

[0363]

[0364] Under nitrogen flow, BCz-D2 (10.0 g, 20.1 mmol) obtained in Preparation Example 5-2, Cz-D1 (7.9 g, 24.1 mmol) obtained in Preparation Example 1-1, Pd(OAc)2 (1.15 g, 1.0 mmol), P(t-Bu)3 (0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol) and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction, toluene was concentrated, and the solid salt was filtered and purified by recrystallization to obtain the target compound B-1 (10.2 g, yield 62%).

[0365] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0366] [Synthesis Example 18] Synthesis of B-2

[0367]

[0368] The same process as in Synthesis Example 17 was carried out except that Cz-D5 (7.9 g, 24.1 mmol) obtained in Preparation Example 2-1 was used instead of Cz-D1 used in Synthesis Example 17, thereby obtaining the target compound B-2 (8.5 g, yield 48%).

[0369] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0370] [Synthesis Example 19] Synthesis of B-3

[0371]

[0372] The same process as in Synthesis Example 17 was carried out except that Cz-D9 (7.9 g, 24.1 mmol) obtained in Preparation Example 3-1 was used instead of Cz-D1 used in Synthesis Example 17, thereby obtaining the target compound B-3 (11.1 g, yield 63%).

[0373] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0374] [Synthesis Example 20] Synthesis of B-4

[0375]

[0376] The same process as Synthesis Example 17 was carried out except that Cz-D13 (7.9 g, 24.1 mmol) obtained in Preparation Example 4-1 was used instead of Cz-D1 used in Synthesis Example 17, thereby obtaining the target compound B-4 (7.42 g, yield 42%).

[0377] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0378] [Synthesis Example 21] Synthesis of C-1

[0379]

[0380] Under nitrogen flow, BCz-D3 (10.0 g, 20.1 mmol) obtained in Preparation Example 5-3, Cz-D1 (7.9 g, 24.1 mmol) obtained in Preparation Example 1-1, Pd(OAc)2 (1.15 g, 1.0 mmol), P(t-Bu)3 (0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol) and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction, toluene was concentrated, and the solid salt was filtered and purified by recrystallization to obtain the target compound C-1 (9.4 g, yield 63%).

[0381] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0382] [Synthesis Example 22] Synthesis of C-2

[0383]

[0384] The same process as Synthesis Example 21 was carried out except that Cz-D5 (7.9 g, 24.1 mmol) obtained in Preparation Example 2-1 was used instead of Cz-D1 used in Synthesis Example 21, thereby obtaining the target compound C-2 (7.78 g, yield 44%).

[0385] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0386] [Synthesis Example 23] Synthesis of C-3

[0387]

[0388] The same process as Synthesis Example 21 was carried out except that Cz-D9 (7.9 g, 24.1 mmol) obtained in Preparation Example 3-1 was used instead of Cz-D1 used in Synthesis Example 21, thereby obtaining the target compound C-3 (11.67 g, yield 66%).

[0389] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0390] [Synthesis Example 24] Synthesis of C-4

[0391]

[0392] The same process as Synthesis Example 21 was carried out except that Cz-D13 (7.9 g, 24.1 mmol) obtained in Preparation Example 4-1 was used instead of Cz-D1 used in Synthesis Example 21, thereby obtaining the target compound C-4 (6.89 g, yield 39%).

[0393] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0394] [Synthesis Example 25] Synthesis of D-1

[0395]

[0396] Under nitrogen flow, BCz-D4 (10.0 g, 20.1 mmol) obtained in Preparation Example 5-4, Cz-D1 (7.9 g, 24.1 mmol) obtained in Preparation Example 1-1, Pd(OAc)2 (1.15 g, 1.0 mmol), P(t-Bu)3 (0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol) and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction, toluene was concentrated, and the solid salt was filtered and purified by recrystallization to obtain the target compound D-1 (8.1 g, yield 54%).

[0397] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0398] [Synthesis Example 26] Synthesis of D-2

[0399]

[0400] The same process as Synthesis Example 25 was carried out except that Cz-D5 (7.9 g, 24.1 mmol) obtained in Preparation Example 2-1 was used instead of Cz-D1 used in Synthesis Example 25, thereby obtaining the target compound D-2 (7.24 g, yield 41%).

[0401] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0402] [Synthesis Example 27] Synthesis of D-3

[0403]

[0404] The same process as in Synthesis Example 25 was carried out except that Cz-D9 (7.9 g, 24.1 mmol) obtained in Preparation Example 3-1 was used instead of Cz-D1 used in Synthesis Example 25, thereby obtaining the target compound D-3 (8.41 g, yield 51%).

[0405] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0406] [Synthesis Example 28] Synthesis of D-4

[0407]

[0408] The same process as Synthesis Example 25 was carried out except that Cz-D13 (7.9 g, 24.1 mmol) obtained in Preparation Example 4-1 was used instead of Cz-D1 used in Synthesis Example 25, thereby obtaining the target compound D-4 (5.47 g, yield 31%).

[0409] Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0410] [Preparation Example 6] Synthesis of DBF-1

[0411] <Step 1> Synthesis of 4-(3-chlorophenyl)-6-phenyldibenzo[b,d]furan

[0412]

[0413] Under a nitrogen flow, 4,4,5,5-tetramethyl-2-(6-phenyldibenzo[b,d]furan-4-yl)-1,3,2-dioxaborolane (100.0 g, 270.0 mmol), 1-bromo-3-chlorobenzene (62.0 g, 324.1 mmol), Pd(PPh3)4 (15.6 g, 13.5 mmol), K2CO3 (93.3 g, 675.2 mmol) and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0414] After the reaction was completed, the mixture was extracted with dichloromethane, and then MgSO4 was added and filtered. Then, the solvent was removed from the obtained organic layer, and then purified by column chromatography (hexane:DCM=9:1 (v / v)) to obtain 4-(3-chlorophenyl)-6-phenyldibenzo[b,d]furan (48.9 g, yield 51%).

[0415] Mass (theoretical value: 354.83, measured value: 354 g / mol)

[0416] <Step 2> Synthesis of DBF-1

[0417]

[0418] Under a nitrogen stream, 4-(3-chlorophenyl)-6-phenyldibenzo[b,d]furan (48.9 g, 137.7 mmol) obtained in the above <Step 1>, 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (38.5 g, 151.5 mmol), Pd(dppf)Cl2 (12.1 g, 13.8 mmol), KOAc (38.9 g, 413.2 mmol) and 1,4-dioxane (1000 ml) were mixed and stirred at 130°C for 12 hours.

[0419] After the reaction, the product was extracted with ethyl acetate, and then water was removed with MgSO 4 , and then purified by column chromatography (hexane:DCM=4:1 (v / v)) to obtain DBF-1 (26.4 g, yield 43%).

[0420] Mass (theoretical value: 446.35, measured value: 446 g / mol)

[0421] [Preparation Example 7] Synthesis of DBF-2

[0422] <Step 1> Synthesis of 4-(4-chlorophenyl)-6-phenyldibenzo[b,d]furan

[0423]

[0424] Under a nitrogen flow, 4,4,5,5-tetramethyl-2-(6-phenyldibenzo[b,d]furan-4-yl)-1,3,2-dioxaborolane (100.0 g, 270.0 mmol), 1-bromo-4-chlorobenzene (62.0 g, 324.1 mmol), Pd(PPh3)4 (15.6 g, 13.5 mmol), K2CO3 (93.3 g, 675.2 mmol) and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0425] After the reaction was completed, the mixture was extracted with dichloromethane, and then MgSO4 was added and filtered. Then, the solvent was removed from the obtained organic layer, and then purified by column chromatography (hexane:DCM=9:1 (v / v)) to obtain 4-(4-chlorophenyl)-6-phenyldibenzo[b,d]furan (60.4 g, yield 63%).

[0426] Mass (theoretical value: 354.83, measured value: 354 g / mol)

[0427] <Step 2> Synthesis of DBF-2

[0428]

[0429] Under a nitrogen stream, 4-(4-chlorophenyl)-6-phenyldibenzo[b,d]furan (60.4 g, 170.2 mmol) obtained in the above <Step 1>, 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (47.5 g, 187.2 mmol), Pd(dppf)Cl2 (14.9 g, 17.0 mmol), KOAc (48.1 g, 510.4 mmol) and 1,4-dioxane (1000 ml) were mixed and stirred at 130°C for 12 hours.

[0430] After the reaction, the product was extracted with ethyl acetate, and then water was removed with MgSO 4 , and purified by column chromatography (hexane:DCM=4:1 (v / v)) to obtain DBF-2 (36.5 g, yield 48%).

[0431] Mass (theoretical value: 446.35, measured value: 446 g / mol)

[0432] [Preparation Example 8] Synthesis of DBF-3

[0433] <Step 1> Synthesis of 3-(3-chlorophenyl)-6-phenyldibenzo[b,d]furan

[0434]

[0435] Under a nitrogen flow, 4,4,5,5-tetramethyl-2-(6-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane (100.0 g, 270.0 mmol), 1-bromo-3-chlorobenzene (62.0 g, 324.1 mmol), Pd(PPh3)4 (15.6 g, 13.5 mmol), K2CO3 (93.3 g, 675.2 mmol) and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0436] After the reaction was completed, the mixture was extracted with dichloromethane, and then MgSO4 was added and filtered. Then, the solvent was removed from the obtained organic layer, and then purified by column chromatography (hexane:DCM=9:1 (v / v)) to obtain 3-(3-chlorophenyl)-6-phenyldibenzo[b,d]furan (68.0 g, yield 71%).

[0437] Mass (theoretical value: 354.83, measured value: 354 g / mol)

[0438] <Step 2> Synthesis of DBF-3

[0439]

[0440] Under a nitrogen stream, 3-(3-chlorophenyl)-6-phenyldibenzo[b,d]furan (68.0 g, 191.8 mmol) obtained in the above <Step 1>, 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (53.6 g, 210.9 mmol), Pd(dppf)Cl2 (16.8 g, 19.2 mmol), KOAc (54.2 g, 575.3 mmol) and 1,4-dioxane (1000 ml) were mixed and stirred at 130°C for 12 hours.

[0441] After the reaction, the product was extracted with ethyl acetate, and then water was removed with MgSO 4 , and purified by column chromatography (hexane:DCM=4:1 (v / v)) to obtain DBF-3 (54.8 g, yield 64%).

[0442] Mass (theoretical value: 446.35, measured value: 446 g / mol)

[0443] [Preparation Example 9] Synthesis of DBF-4

[0444] <Step 1> Synthesis of 1-(3-chlorophenyl)-6-phenyldibenzo[b,d]furan

[0445]

[0446] Under a nitrogen flow, 4,4,5,5-tetramethyl-2-(6-phenyldibenzo[b,d]furan-1-yl)-1,3,2-dioxaborolane (100.0 g, 270.0 mmol), 1-bromo-3-chlorobenzene (62.0 g, 324.1 mmol), Pd(PPh3)4 (15.6 g, 13.5 mmol), K2CO3 (93.3 g, 675.2 mmol) and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0447] After the reaction was completed, the mixture was extracted with dichloromethane, and then MgSO4 was added and filtered. Then, the solvent was removed from the obtained organic layer, and then purified by column chromatography (hexane:DCM=9:1 (v / v)) to obtain 1-(3-chlorophenyl)-6-phenyldibenzo[b,d]furan (62.3 g, yield 65%).

[0448] Mass (theoretical value: 354.83, measured value: 354 g / mol)

[0449] <Step 2> Synthesis of DBF-4

[0450]

[0451] Under a nitrogen stream, 1-(3-chlorophenyl)-6-phenyldibenzo[b,d]furan (62.3 g, 175.6 mmol) obtained in the above <Step 1>, 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (49.0 g, 193.1 mmol), Pd(dppf)Cl2 (15.4 g, 17.6 mmol), KOAc (49.6 g, 526.7 mmol) and 1,4-dioxane (1000 ml) were stirred at 130°C for 12 hours.

[0452] After the reaction, the product was extracted with ethyl acetate, and then water was removed with MgSO 4 , and purified by column chromatography (hexane:DCM=4:1 (v / v)) to obtain DBF-4 (45.4 g, yield 58%).

[0453] Mass (theoretical value: 446.35, measured value: 446 g / mol)

[0454] [Preparation Example 10] Synthesis of DBF-5

[0455] <Step 1> Synthesis of 1-(3-chlorophenyl)-9-phenyldibenzo[b,d]furan

[0456]

[0457] Under a nitrogen flow, 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-1-yl)-1,3,2-dioxaborolane (100.0 g, 270.0 mmol), 1-bromo-3-chlorobenzene (62.0 g, 324.1 mmol), Pd(PPh3)4 (15.6 g, 13.5 mmol), K2CO3 (93.3 g, 675.2 mmol) and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0458] After the reaction was completed, the mixture was extracted with dichloromethane, and then MgSO4 was added and filtered. Then, the solvent was removed from the obtained organic layer, and then purified by column chromatography (hexane:DCM=9:1 (v / v)) to obtain 1-(3-chlorophenyl)-9-phenyldibenzo[b,d]furan (68.0 g, yield 71%).

[0459] Mass (theoretical value: 354.83, measured value: 354 g / mol)

[0460] <Step 2> Synthesis of DBF-5

[0461]

[0462] Under a nitrogen stream, 1-(3-chlorophenyl)-9-phenyldibenzo[b,d]furan (68.0 g, 191.8 mmol) obtained in the above <Step 1>, 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (53.6 g, 210.9 mmol), Pd(dppf)Cl2 (16.8 g, 19.2 mmol), KOAc (54.2 g, 575.3 mmol) and 1,4-dioxane (1000 ml) were mixed and stirred at 130°C for 12 hours.

[0463] After the reaction, the product was extracted with ethyl acetate, and then water was removed with MgSO 4 , and purified by column chromatography (hexane:DCM=4:1 (v / v)) to obtain DBF-5 (41.9 g, yield 49%).

[0464] Mass (theoretical value: 446.35, measured value: 446 g / mol)

[0465] [Synthesis Example 29] Synthesis of E-1

[0466]

[0467] Under a nitrogen flow, DBF-1 (10.0 g, 22.4 mmol) obtained in Preparation Example 6, 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (9.6 g, 26.9 mmol), Pd(PPh3)4 (1.3 g, 1.1 mmol), K2CO3 (7.7 g, 56.0 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0468] After the reaction was completed, the mixture was extracted with dichloromethane, and then MgSO4 was added and filtered. Then, the solvent was removed from the obtained organic layer, and the mixture was purified by column chromatography (hexane:EA=4:1 (v / v)) to obtain the target compound E-1 (11.8 g, yield 82%).

[0469] Mass (theoretical value: 641.73, measured value: 641 g / mol)

[0470] [Synthesis Example 30] Synthesis of E-2

[0471]

[0472] 2-(3-bromophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (12.9 g, 26.9 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine used in Synthesis Example 29. Except for this, the same process as Synthesis Example 29 was carried out to obtain the target compound E-2 (11.9 g, yield 74%).

[0473] Mass (theoretical value: 717.83, measured value: 717 g / mol)

[0474] [Synthesis Example 31] Synthesis of E-3

[0475]

[0476] 2-(3-bromophenyl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (12.9 g, 26.9 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine used in Synthesis Example 29. Except for this, the same process as Synthesis Example 29 was carried out to obtain the target compound E-3 (11.4 g, yield 71%).

[0477] Mass (theoretical value: 717.83, measured value: 717 g / mol)

[0478] [Synthesis Example 32] Synthesis of E-4

[0479]

[0480] 2-(4-bromophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (12.9 g, 26.9 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine used in Synthesis Example 29. Except for this, the same process as Synthesis Example 29 was carried out to obtain the target compound E-4 (12.7 g, yield 79%).

[0481] Mass (theoretical value: 717.83, measured value: 717 g / mol)

[0482] [Synthesis Example 33] Synthesis of E-5

[0483]

[0484] The DBF-4 (10.0 g, 22.4 mmol) obtained in Preparation Example 9 was used instead of the DBF-1 (10.0 g, 22.4 mmol) used in Synthesis Example 29, and 2-(3-bromophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (12.9 g, 26.9 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine. Except for this, the same process as Synthesis Example 29 was carried out to obtain the target compound E-5 (9.8 g, yield 61%).

[0485] Mass (theoretical value: 717.83, measured value: 717 g / mol)

[0486] [Synthesis Example 34] Synthesis of E-6

[0487]

[0488] Using 2-([1,1':3',1"-triphenyl]-5'-yl)-4-chloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine (13.7 g, 26.9 mmol) instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine used in Synthesis Example 29, the same process as Synthesis Example 29 was carried out to obtain the target compound E-6 (9.6 g, yield 54%).

[0489] Mass (theoretical value: 793.93, measured value: 793 g / mol)

[0490] [Synthesis Example 35] Synthesis of E-7

[0491]

[0492] The DBF-4 (10.0 g, 22.4 mmol) obtained in Preparation Example 9 was used instead of the DBF-1 (10.0 g, 22.4 mmol) used in Synthesis Example 29, and 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine (12.5 g, 26.9 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine. Except for this, the same process as Synthesis Example 29 was carried out to obtain the target compound E-7 (9.8 g, yield 62%).

[0493] Mass (theoretical value: 703.85, measured value: 703 g / mol)

[0494] [Synthesis Example 36] Synthesis of E-8

[0495]

[0496] The DBF-3 (10.0 g, 22.4 mmol) obtained in Preparation Example 8 was used instead of the DBF-1 (10.0 g, 22.4 mmol) used in Synthesis Example 29, and 2-(3-bromophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (12.9 g, 26.9 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine. Except for this, the same process as Synthesis Example 29 was carried out to obtain the target compound E-8 (10.8 g, yield 67%).

[0497] Mass (theoretical value: 717.83, measured value: 717 g / mol)

[0498] [Synthesis Example 37] Synthesis of E-9

[0499]

[0500] The DBF-3 (10.0 g, 22.4 mmol) obtained in Preparation Example 8 was used instead of the DBF-1 (10.0 g, 22.4 mmol) used in Synthesis Example 29, and 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine (12.5 g, 26.9 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine. Except for this, the same process as Synthesis Example 29 was carried out to obtain the target compound E-9 (11.4 g, yield 72%).

[0501] Mass (theoretical value: 703.85, measured value: 703 g / mol)

[0502] [Synthesis Example 38] Synthesis of E-10

[0503]

[0504] The DBF-5 (10.0 g, 22.4 mmol) obtained in Preparation Example 10 was used instead of the DBF-1 (10.0 g, 22.4 mmol) used in Synthesis Example 29, and 2-([1,1'-biphenyl]-3-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine (12.5 g, 26.9 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine. Except for this, the same process as Synthesis Example 29 was carried out to obtain the target compound E-10 (10.4 g, yield 66%).

[0505] Mass (theoretical value: 703.85, measured value: 703 g / mol)

[0506] [Preparation Example 11] Synthesis of DBF-6

[0507] <Step 1> 4-(3'-chloro-[1,1'-biphenyl]-3-yl-2,2',4,4',5,5',6,6'-d8)-6-(phenyl-d5) Synthesis of dibenzo[b,d]furan-1,2,3,7,8,9-d6

[0508]

[0509] Under a nitrogen flow, 4,4,5,5-tetramethyl-2-(6-(phenyl-d5)dibenzo[b,d]furan-4-yl-1,2,3,7,8,9-d6)-1,3,2-dioxaborolane (100.0 g, 262.2 mmol), 3-bromo-3'-chloro-1,1'-biphenyl-2,2',4,4',5,5',6,6'-d8 (86.7 g, 314.7 mmol), Pd(PPh3)4 (15.2 g, 13.1 mmol), K2CO3 (90.6 g, 655.6 mmol) and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0510] After the reaction, extraction with dichloromethane was performed, and then MgSO4 was added and filtered. After the solvent was removed from the obtained organic layer, column chromatography (hexane: DCM = 9: 1 (v / v)) was used for purification to obtain 4-(3'-chloro-[1,1'-biphenyl]-3-yl-2,2',4,4',5,5',6,6'-d8)-6-(phenyl-d5)dibenzo[b,d]furan-1,2,3,7,8,9-d6 (83.8 g, yield 71%).

[0511] Mass (theoretical value: 450.05, measured value: 450 g / mol)

[0512] <Step 2> Synthesis of DBF-6

[0513]

[0514] Under a nitrogen stream, 4-(3'-chloro-[1,1'-biphenyl]-3-yl-2,2',4,4',5,5',6,6'-d8)-6-(phenyl-d5)dibenzo[b,d]furan-1,2,3,7,8,9-d6 (83.8 g, 186.2 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (52.0 g, 204.8 mmol), Pd(dppf)Cl2 (16.3 g, 18.6 mmol), KOAc (52.6 g, 558.6 mmol) and 1,4-dioxane (1000 ml) were mixed and stirred at 130°C for 12 hours.

[0515] After the reaction, the product was extracted with ethyl acetate, and then water was removed with MgSO 4 , and purified by column chromatography (hexane:DCM=4:1 (v / v)) to obtain DBF-6 (64.5 g, yield 64%).

[0516] Mass (theoretical value: 541.57, measured value: 541 g / mol)

[0517] [Synthesis Example 39] Synthesis of E-11

[0518]

[0519] Under a nitrogen flow, DBF-6 (10.0 g, 18.5 mmol) prepared in Example 11, 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.9 g, 22.2 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), K2CO3 (6.4 g, 46.2 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0520] After the reaction, the mixture was extracted with dichloromethane, and then MgSO4 was added and filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (hexane:EA=4:1 (v / v)) to obtain the target compound E-11 (9.9 g, yield 73%).

[0521] Mass (theoretical value: 736.94, measured value: 736 g / mol)

[0522] [Synthesis Example 40] Synthesis of E-12

[0523]

[0524] The target compound E-12 (10.0 g, yield 75%) was obtained by carrying out the same process as Synthesis Example 39, except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.6 g, 22.2 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine.

[0525] Mass (theoretical value: 722.96, measured value: 722 g / mol)

[0526] [Synthesis Example 41] Synthesis of E-13

[0527]

[0528] The target compound E-13 (9.3 g, yield 77%) was obtained by carrying out the same process as Synthesis Example 39, except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.2 g, 22.2 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine.

[0529] Mass (theoretical value: 656.92, measured value: 656 g / mol)

[0530] [Example 1] Preparation of green organic EL element

[0531] Compound A-1 synthesized in Synthesis Example 1 and Compound E-1 synthesized in Synthesis Example 29 were purified by sublimation to high purity according to a commonly known method, and then a green organic EL device was prepared according to the following process.

[0532] First, we will The glass substrate coated with a thin film of indium tin oxide (ITO) was washed with distilled water ultrasonic. After the distilled water washing, it was ultrasonically cleaned with isopropyl alcohol, acetone, methanol and other solvents and dried, and then transferred to a UV OZONE cleaning machine (Power sonic 405, Hwashintech), and then the substrate was cleaned with UV for 5 minutes, and then the substrate was transferred to a vacuum evaporator.

[0533] On the ITO transparent electrode prepared in this way, 98wt% HT+2wt% / 60wt% of compound A-1+30wt% of compound E-1+10wt% Ir(ppy)3 / ET+LiQ( 1:1 molar ratio) / LiF /

[0534] The organic EL element is produced by stacking them in this order.

[0535] At this time, the structures of HT, PA, HA, EA, ET and Ir(ppy)3 used are as follows.

[0536]

[0537] [Example 2] to [Example 292] - Manufacture of green organic EL elements

[0538] A green organic EL element was manufactured in the same manner as in Example 1, except that compounds A-1 to D-4 described in Table 1 were used instead of compound A-1 used as the main body 1 in the light-emitting main material when forming the light-emitting layer in Example 1, and compounds E-2 to E-13 described in Table 1 were used instead of compound E-1 used as the main body 2.

[0539] [Comparative Example 1] to [Comparative Example 12] Preparation of Green Organic EL Devices

[0540] A green organic EL element was prepared by the same process as in Example 1 except that the following compounds HT-1 to HT-4 were used instead of the compound A-1 used as the host 1 in the light-emitting host material when the light-emitting layer was formed in Example 1, and the following compounds ET-1 to ET-7 were used instead of the compound E-1 used as the host 2. At this time, the structures of the compounds HT-1 to HT-4 and ET-1 to ET-7 used are as follows.

[0541]

[0542] [Evaluation Example 1]

[0543] The current density of the green organic EL devices prepared in Examples 1 to 292 and Comparative Examples 1 to 12 was measured at 10 mA / cm 2 The driving voltage, current efficiency, luminescence peak and life span are shown in Table 1 below.

[0544] [Table 1]

[0545]

[0546]

[0547]

[0548]

[0549]

[0550]

[0551]

[0552]

[0553]

[0554]

[0555]

[0556]

[0557]

[0558] As shown in Table 1 above, it can be seen that the green organic EL elements of Examples 1 to 292 according to the present invention, which simultaneously contain the compounds (A-1 to D-4) of Chemical Formula 1 as the first host (P-type host) and the compounds (E-1 to E-13) of Chemical Formula 2 as the second host (N-type host) as the host materials of the light-emitting layer, show more excellent performance in current efficiency, driving voltage and life characteristics compared with the green organic EL elements of Comparative Examples 1 to 12 in which HT-1 to HT-4 and ET-1 to ET-7 were used as host materials.

[0559] In addition, it can be seen that the green organic EL elements of Examples 281 to 292 containing deuterium-substituted compounds (E-11 to E-13) as the second host (N-type host) show more excellent performance in terms of current efficiency, driving voltage and life characteristics compared to the organic EL elements of Examples 1 to 280 containing undeuterium-substituted compounds (E-1 to E10) as the second host (N-type host). This is because the CD bond with a higher dissociation energy than the CH bond is applied to the N-type host as an electronic property material in the element in the form of deuterium substitution, thereby improving the stability of the single molecule itself. That is, under the same structure, the deuterium-substituted compound (for example: E-11 to E-13) can produce relatively more excitons than the undeuterium-substituted compound (for example: E-1 to E-10), and the generation of excitons leads to reduced thermal denaturation.

Claims

1. A composition for an organic electroluminescent element, comprising a first host represented by the following chemical formula 1 and a second host represented by the following chemical formula 2: [Chemical formula 1] [Chemical formula 2] In the chemical formulas 1 and 2, D is deuterium, a, d, f and h are integers from 0 to 3, b, c, e, g and i are each an integer from 0 to 4, j and k are each an integer from 0 to 5, n1 is an integer from 1 to 5, n2 is an integer of 0 or 1, X1 is selected from the group consisting of O, S, Se, N(Ar3), C(Ar4)(Ar5) and Si(Ar6)(Ar7), Y1 and Y2 are the same as or different from each other and are independently N or C(Ar8). In this case, at least one of Y1 and Y2 is N. Ar1 to Ar8 and R1 to R5 are the same as or different from each other, and each independently can be selected from hydrogen, deuterium (D), halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, phosphine oxide, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 or they form a condensed ring with adjacent groups, The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, alkylphosphine oxide, arylphosphine oxide, arylamine and condensed ring of Ar1 to Ar8 and R1 to R5 are each independently selected from deuterium, halogen, cyano, nitro, C2 to C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C1~C 40 Alkyl, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 The group consisting of the arylamine groups may be substituted or unsubstituted with one or more substituents, and when there are plural substituents, they may be the same as or different from each other. 2 . The composition for an organic electroluminescent element according to claim 1 , wherein the number of deuterium (D) contained in the first host is at least 13. 3 .

3. The composition for an organic electroluminescent element according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other and are each independently a substituent selected from the group consisting of the following substituents S1 to S4:

4. The composition for an organic electroluminescent element according to claim 1, wherein the first host represented by Chemical Formula 1 is a compound represented by the following Chemical Formula 3: [Chemical formula 3] In the chemical formula 3, a, b, c, d, e and f are each as defined in claim 1, m1 and m2 are 0 or 1, respectively.

5. The composition for an organic electroluminescent element according to claim 1, wherein the first host represented by Chemical Formula 1 is a compound represented by the following Chemical Formula 4: [Chemical formula 4] In the chemical formula 4, a, b, c, d, e and f are each as defined in claim 1, m1 and m2 are 0 or 1, respectively.

6. The composition for an organic electroluminescent element according to claim 1, wherein the first host represented by Chemical Formula 1 is a compound represented by the following Chemical Formula 5: [Chemical formula 5] In the chemical formula 5, a, b, c, d, e and f are each as defined in claim 1, m1 and m2 are 0 or 1, respectively.

7. The composition for an organic electroluminescent element according to claim 1, wherein the first host represented by Chemical Formula 1 is a compound selected from the group consisting of the following compounds A-1 to D-4:

8. The composition for an organic electroluminescent element according to claim 1, wherein in the second host represented by Chemical Formula 2, The moiety is a moiety selected from the group consisting of the following moieties Mo-1 to Mo-3: In the parts Mo-1 to Mo-3, * is the site connected to the chemical formula 2, Y1 and Y2 are each independently C(Ar8), Ar8 has the same meaning as defined in claim 1.

9. The composition for an organic electroluminescent element according to claim 1, wherein in the chemical formula 2, The moiety is a moiety selected from the group consisting of the following moieties Dz-1 to Dz-32: Among the Dz-1 to Dz-32, R1 is C6~C 60 The aromatic group.

10. The composition for an organic electroluminescent element according to claim 1, wherein the second host represented by Chemical Formula 2 is a compound represented by the following Chemical Formula 6: [Chemical formula 6] In the chemical formula 6, i, j, k, R1, R3 to R5, n1, n2, X1, Y1 and Y2 are each the same as defined in claim 1.

11. The composition for an organic electroluminescent element according to claim 1, wherein the second host represented by Chemical Formula 2 is a compound represented by the following Chemical Formula 7 or 8: [Chemical formula 7] [Chemical formula 8] In the chemical formulas 7 and 8, i, k, R1, R3, R5, n1, n2, Y1 and Y2 are each as defined in claim 1, X1 and X2 are each O or S.

12. The composition for an organic electroluminescent element according to claim 1, wherein the second host represented by Chemical Formula 2 is a compound represented by the following Chemical Formula 9 or 10: [Chemical formula 9] [Chemical formula 10] In the chemical formulas 9 and 10, n1, n2, Y1 and Y2 are each the same as defined in claim 1, x and y are 0 or 1 respectively, X1 and X2 are each O or S, D is deuterium, o1 is an integer from 0 to 5, o2 is an integer from 0 to 6, o3 is an integer from 0 to 4, o4 is an integer from 0 to 3, o5 is an integer from 0 to 7.

13. The composition for an organic electroluminescent element according to claim 1, wherein the second host represented by Chemical Formula 2 is selected from the group consisting of the following compounds E-1 to E-13: 14 . The composition for an organic electroluminescent element according to claim 1 , comprising the first host and the second host in a weight ratio of 99:1 to 1:

99. 15 . The composition for an organic electroluminescent element according to claim 1 , further comprising a phosphorescent dopant. 16 . The composition for an organic electroluminescent element according to claim 15 , wherein the phosphorescent dopant is a metal complex containing iridium (Ir) or platinum (Pt).

17. An organic electroluminescent element comprising an anode, a cathode and one or more organic layers between the anode and the cathode, The one or more organic layers comprise the composition according to any one of claims 1 to 16.

18. The organic electroluminescent element according to claim 17, wherein the one or more organic layers include a light-emitting layer, The composition is contained in the light-emitting layer.

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