Composition for organic electroluminescence device and organic electroluminescence device containing the same

Abstract

The present invention relates to a composition for an organic electroluminescence device, and an organic electroluminescence device containing the same, the composition for an organic electroluminescence device comprising a first host represented by [Chemical Formula 1] and a second host represented by [Chemical Formula 2], wherein the above [Chemical Formula 1] and [Chemical Formula 2] are as defined in the specification.

Description

[Technical field]

[0001] The present invention relates to a composition for an organic electroluminescence device, and an organic electroluminescence device containing the same. [Background technology]

[0002] When a voltage is applied between the two electrodes of an organic electroluminescence element (hereinafter referred to as "organic EL element"), holes are injected from the positive electrode and electrons are injected from the negative electrode into the organic layer. When the injected holes and electrons meet, excitons are formed, and light is emitted when these excitons return to the ground state. At this time, the materials used in the organic layer are classified according to their functions into light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, electron-injecting materials, etc.

[0003] The materials forming the light-emitting layer of an organic EL device can be classified into blue, green, and red light-emitting materials according to the color of the light emitted. Furthermore, yellow and orange light-emitting materials can be used as light-emitting materials to achieve better natural colors. In addition, host / dopant systems are used as light-emitting materials to improve color purity and luminous efficiency through energy transfer. Dopant materials are broadly classified into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. Such phosphorescent materials can theoretically improve the luminous efficiency by four times compared to fluorescence, so interest is focused not only on phosphorescent dopants but also on phosphorescent host materials.

[0004] Currently, NPB, BCP, Alq3, etc. are widely known as materials used for the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer, and anthracene derivatives have been reported as fluorescent dopant / host materials for light-emitting materials. In particular, among light-emitting materials, metal complex compounds containing Ir such as Firpic, Ir(ppy)3, (acac)Ir(btp)2, etc., are used as blue, green, and red dopant materials as phosphorescent materials that have great advantages in terms of improving efficiency. Currently, CBP shows excellent properties as a phosphorescent host material.

[0005] However, conventional organic layer materials, although advantageous in terms of light-emitting properties, have low glass transition temperatures and poor thermal stability, resulting in an unsatisfactory life span in organic EL devices. Therefore, there is a demand for the development of organic layer materials with superior performance. Summary of the Invention [Problem to be solved by the invention]

[0006] An object of the present invention is to provide a composition capable of realizing an organic EL device having high efficiency and long life.

[0007] Another object of the present invention is to provide an organic EL device which contains the above composition as an organic layer material (for example, a light-emitting layer material) and thereby exhibits improved low driving voltage, high light-emitting efficiency, and long life characteristics. [Means for solving the problem]

[0008] In order to achieve the above-mentioned object, the present invention provides a composition for an organic EL device, comprising a first host represented by the following [Chemical Formula 1] and a second host represented by the following [Chemical Formula 2]: [ka] [ka] In the above formula, Ar1 and Ar2 are the same or different and each independently represents C1 to C 40 Alkyl groups, C2-C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 6 to 40 ring atoms, 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C1-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron groups, phosphine oxide groups, C1-C 40 Alkyl phosphine oxide group, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide groups, and C6-C 60 and wherein the aryl amine group is selected from the group consisting of X1 to X3 are the same or different and each independently represents N or C(R6), provided that at least two of X1 to X3 are N; L is a single bond or a C6-C 60 and heteroarylene groups having 5 to 60 ring atoms, A is a substituent represented by the following [Chemical Formula 3] and [Chemical Formula 4], [ka] [ka] In the above formula, Z is selected from the group consisting of O, S, Se, and C(R7)(R8); R1 to R8 are the same or different and each independently represent a hydrogen atom, a deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1 to C 40 Alkyl groups, C2-C 40Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 6 to 40 ring atoms, 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C1-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron group, phosphine oxide group, C1-C 40 Alkyl phosphine oxide group, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide groups, and C6-C 60 or which may be joined to adjacent groups to form a fused ring; a, d, and f each independently represent an integer of 0 to 3; b, c, e, g, i, j, and k each independently represent an integer of 0 to 4; In the above [chemical formula 1], the hydrogen in the benzene ring of the carbazole in which the deuterium (D) is not substituted is C1-C 40 Alkyl groups of C6 to C 40 and a heteroaryl group having 5 to 40 ring atoms, The arylene group and heteroarylene group of L, and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, alkylphosphine oxide group, arylphosphine group, arylphosphine oxide group, arylamine group, and fused ring of Ar1 to Ar2 and R1 to R8 each independently represent deuterium (D), halogen, cyano group, nitro group, C2 to C6 40 Alkenyl groups, C2-C 40Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 1 to 40 ring atoms, C1 to C 40 Alkyl groups of C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C1-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron groups, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide groups, and C6-C 60 and when there are a plurality of the above-mentioned substituents, they may be the same or different. Effect of the Invention

[0009] According to one embodiment of the present invention, by using a compound having high hole properties and a compound having high electronic properties in combination as a host, it is possible to realize an organic EL device that has low driving voltage, high efficiency, and long life properties, as well as excellent phosphorescence generation properties.

[0010] The effects of the present invention are not limited to the above-mentioned contents, and more various effects are included in the present specification. [Brief description of the drawings]

[0011] [Figure 1] FIG. 1 is a cross-sectional view showing a structure of an organic EL element according to an embodiment of the present invention. [Explanation of symbols]

[0012] 100: Positive electrode 200: Negative electrode 300:Organic layer 310: Hole transport region 311: Hole injection layer 312: Hole transport layer 320: Light-emitting layer 330: Electron transport area 331: Electron transport layer 332: Electron injection layer DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0013] The advantages and features of the present invention, as well as the methods for achieving them, will be apparent from the embodiments described in detail with reference to the accompanying drawings. However, the present invention is not limited to the embodiments disclosed below, and can be modified and embodied in various different forms. However, the embodiments described below are provided for the purpose of complete disclosure of the present invention, and for those skilled in the art to which the present invention pertains to fully understand the scope of the invention, and the present invention should be defined by the scope of the claims. Therefore, in some embodiments, detailed descriptions of well-known processes and steps, well-known device structures, and well-known techniques will be omitted to avoid ambiguous interpretation of the present invention. The same reference numerals refer to the same components throughout this specification.

[0014] Unless otherwise defined, all terms (including technical and scientific terms) used in this specification have the meaning commonly understood by those having ordinary knowledge in the technical field to which the present invention belongs. In addition, terms defined in commonly used dictionaries are not interpreted ideally or excessively unless otherwise specified.

[0015] Furthermore, throughout this specification, when a part "includes" a certain component, it does not mean that other components are excluded, but that other components may be further included, unless otherwise specified. Note that throughout this specification, "above" or "on" includes not only the case where the part is located above or below the target part, but also the case where there is another part between them, and does not necessarily mean that the part is located above the direction of gravity.

[0016] Moreover, in this specification, the terms "first", "second", etc. do not denote any order or importance, but are used to distinguish elements.

[0017] <Composition for organic EL devices> The composition for an organic EL device according to the present invention is a composition for forming an organic layer (e.g., an emitting layer) of an organic EL device, and contains a first host represented by the above [Chemical Formula 1] and a second host represented by the above [Chemical Formula 2].

[0018] The first host represented by the above [Chemical Formula 1] is a compound in which at least three carbazoles are directly bonded without a linker, and is a P-type host with relatively high hole properties. The second host represented by the above [Chemical Formula 2] is a compound with an asymmetric structure in which an azine group and a carbazole group having various substituents (e.g., R3-containing ring, A) are introduced, and these are linked by a direct bond or via a linker (L), and is an N-type host with relatively high electronic properties. By using such a first host and a second host in combination, the composition according to the present invention can realize an organic EL device with high efficiency and long life.

[0019] Specifically, the first host is a new P-type host composed of triscarbazole, and has stronger hole character than existing host materials, thereby maximizing the performance of N-type hosts, especially the second host. In addition, since the hole stability is improved compared to existing P-type host materials, the device can continue to maintain stable life characteristics even in the initial characteristics. As a result, when a P-type host composed of at least three or more carbazole groups is provided, the hole stability of the device itself is high, making it possible to manufacture a high-performance OLED device.

[0020] In addition, the first host may have at least 13, specifically at least 15, more specifically at least 21 deuterium (D) substituted on three or more carbazole groups. Since deuterium (D) has a higher molecular mass and a lower zero-point energy than hydrogen (H), deuterium is relatively less likely to dissociate during a reaction. Due to this low zero-point energy, bond dissociation energy increases, reducing reactivity, and thus increasing the stability of molecules containing deuterium. Therefore, the first host maximizes the green color purity compared to a compound having the same structure but without deuterium, and the weakened carbon-hydrogen intramolecular bond is strengthened, improving the stability of the material and significantly improving the life characteristics of the device.

[0021] Furthermore, the second host is an N-type host having an asymmetric structure, which contains an intramolecular azine group (e.g., pyrimidine, triazine) and a carbazole group, and which are linked directly or via a linker (L). When an N-type second host having high electronic properties is used in combination with a P-type first host having relatively high hole properties and represented by the above [Chemical Formula 1], a rapid hole and electron transport effect can be obtained, the efficiency of the device can be improved, and the stability of the light-emitting layer (EML) can be improved, thereby optimizing the performance of the organic EL device.

[0022] Specifically, in the first host represented by the above [Chemical Formula 1], a, d, and f are each an integer of 0 to 3, and b, c, and e are each an integer of 0 to 4. Here, when a, b, c, d, e, f, and e are each 0, it means that hydrogen is not replaced with deuterium (D). On the other hand, when a, d, and f are each an integer of 1 to 3, and when b, c, and e are each an integer of 1 to 4, it means that one or more hydrogens are replaced with deuterium (D). In this case, 13≦a+b+c+d+e+f≦21 may be satisfied. As an example, the number of deuterium (D) contained in the first host may be 13 or more, specifically, at least 21. Preferably, in the above [Chemical Formula 1], a=d=f=3, b=c=e=4, and the number of deuterium (D) is 21 or more. Such a first host can increase the stability of the chemical structure by substitution with deuterium (D), and can simultaneously achieve the characteristics of an organic EL device, such as low voltage, high efficiency, and long life characteristics of the device.

[0023] Such a deuterium (D) may be substituted with another substituent (R). When there are a plurality of R's, they may be the same or different and each independently represents a halogen group, a cyano group, a nitro group, an amino group, a C1-C 40 Alkyl groups, C2-C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 6 to 40 ring atoms, 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy, C6-C 60 Aryloxy groups, C1-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron groups, phosphine oxide groups, C1-C 40 Alkyl phosphine oxide group, C6-C 60 Arylphosphine groups, C6-C 60Arylphosphine oxide groups, and C6-C 60 Specifically, the hydrogen in the benzene ring of the carbazole in which the deuterium (D) is not substituted may be selected from the group consisting of C1 to C 40 Alkyl groups of C6 to C 40 and heteroaryl groups having 5 to 40 ring atoms.

[0024] In the first host represented by the above [chemical formula 1], various substituents, Ar1 and Ar2, may be introduced to the N-positions of the two carbazole groups located at both ends of the three carbazole groups (Cz). Such Ar1 and Ar2 may be the same or different, and each independently represents hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1-C 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 6 to 40 ring atoms, 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C1-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron group, phosphine oxide group, C1-C 40 Alkyl phosphine oxide group, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide groups, and C6-C 60 Specifically, Ar1 and Ar2 are the same or different, and each independently represents an arylamine group having a C6 to C 60 More specifically, Ar1 and Ar2 are each independently selected from the group consisting of an aryl group having a ring atom number of 6 to 60, and a heteroaryl group having a ring atom number of 5 to 60. 40The aryl groups Ar1 to Ar2 are each independently selected from the group consisting of deuterium (D), C6 to C 40 and heteroaryl groups having 5 to 40 ring atoms, and when there are a plurality of the above-mentioned substituents, they may be the same or different. Here, the aryl groups of Ar1 to Ar2 may be unsubstituted with deuterium (D) or may be partially substituted with at least one or more deuterium (D), provided that the case where all of the aryl groups of Ar1 to Ar2 are substituted with deuterium (D) may be excluded.

[0025] In particular, in order to confirm the deuteration effect, it is preferable that the compound represented by the above [Chemical Formula 1] has a deuterium ratio of at least 67%, and there is no particular upper limit.

[0026] In a specific example, Ar1 and Ar2 may be the same or different and each independently may be any one selected from the group consisting of the following substituents S1 to S9, but are not limited thereto. [ka] In the above formula, * is a bonding site with the above [Chemical Formula 1].

[0027] Depending on the types of Ar1 and Ar2, the first host represented by [Chemical Formula 1] above may be a compound represented by [Chemical Formula 1A] below, but is not limited thereto.

[0028] [ka] In the above formula, a, b, c, d, e, f, Ar1, and Ar2 are as defined above in [Chemical Formula 1], m1 and m2 are each 0 or 1.

[0029] In one embodiment of the present invention, the first host represented by [Chemical Formula 1] above may be embodied as any one of [Chemical Formula 1a] to [Chemical Formula 1d] below depending on the bonding positions between the three carbazole groups. [ka] [ka] [ka] [ka] In the above formula, a, b, c, d, e, f, Ar1, and Ar2 are as defined above in [Chemical Formula 1], m1 and m2 are each 0 or 1.

[0030] The compounds represented by the above [Chemical Formula 1a] to [Chemical Formula 1d] can ensure better hole stability in terms of structure. More preferably, the compound represented by the above [Chemical Formula 1c] has at least three carbazole groups bonded to the 3-position, which is the active site of the carbazole group.

[0031] The first host represented by [Chemical Formula 1] according to the present invention may be embodied as any one of the following compounds A-1 to D-4, however, the compound represented by [Chemical Formula 1] according to the present invention is not limited to these examples. [ka] [ka]

[0032] The second host according to the present invention, represented by the above [Chemical Formula 2], has an asymmetric structure containing an azine group (e.g., a heterocycle containing X1 to X3) and a carbazole group, which are linked directly or via a linker (L).

[0033] In the above [Chemical Formula 2], X1 to X3 are the same or different and each independently represent N or C(R6), provided that at least two of X1 to X3 are N. Such nitrogen-containing heterocycles (e.g., X1 to X3-containing rings) contain at least two nitrogen atoms in a monocyclic heteroaryl group (e.g., azine), and therefore exhibit superior electron absorption properties and are advantageous for electron injection and transport.

[0034] Here, R6 is hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1-C 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 6 to 40 ring atoms, 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C1-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron groups, C1-C 40 Phosphine groups, C1-C 40 Phosphine oxide groups, and C6-C 60 Specifically, R6 may be selected from the group consisting of hydrogen, deuterium (D), halogen, cyano group, C1-C 40 Alkyl groups of C6 to C 60 and heteroaryl groups having 5 to 60 ring atoms.

[0035] The heterocycle containing X1 to X3 in the second host may be substituted with various substituents, for example, C6 to C 60and heteroaryl groups having 5 to 60 ring atoms. Specifically, one of the substituents introduced into the X1 to X3-containing heterocycle is an aryl group (e.g., an R3-containing ring), and the other may be represented by any one of the following [Chemical Formula 3] or [Chemical Formula 4]. [ka] [ka] In the above formula, n is an integer from 1 to 3, Z is selected from the group consisting of O, S, Se, and C(R7)(R8). Depending on Z, the dibenzo-based moiety may be a monovalent dibenzofuran group, a monovalent dibenzothiophene group, a monovalent fluorene group, etc. In addition, the case where Z is a monovalent dibenzoselenophene group also falls within the scope of the present invention.

[0036] R3 to R8, which are substituents introduced into the X1 to X3-containing heterocycle, are the same or different and each independently represent a hydrogen atom, a deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1 to C2 40 Alkynyl groups, C2-C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 6 to 40 ring atoms, 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C1-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron group, phosphine oxide group, C1-C 40 Alkyl phosphine oxide group, C6-C 60 Arylphosphine groups, C6-C 60Arylphosphine oxide groups, and C6-C 60 or they may be bonded to adjacent groups to form a condensed ring. Specifically, R3 to R8 are each independently selected from the group consisting of hydrogen, deuterium (D), halogen, a cyano group, C1 to C 40 Alkyl groups of C6 to C 60 and heteroaryl groups having 5 to 60 ring atoms. In this case, the number of substituents of R3 to R5 is not particularly limited, and as an example, i, j, and k are each independently an integer of 0 to 4. Here, the fused ring is a C3 to C 60 Condensed aliphatic rings (specifically, C3 to C 30 (condensed aliphatic rings), C6-C 60 Condensed aromatic rings (specifically, C6 to C 30 fused heteroaromatic rings having 5 to 60 members (specifically, fused heteroaromatic rings having 5 to 30 members), C3 to C 60 and combinations thereof.

[0037] The benzene rings on both sides of the carbazole group bonded to the X1 to X3-containing heterocycle may each be substituted with R1 and R2 as various substituents.

[0038] R1 and R2 are the same or different and each independently represent a hydrogen atom, a deuterium atom (D), a halogen atom, a cyano group, a nitro group, an amino group, a nitro group, an amino group, a C1 to C 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 6 to 40 ring atoms, 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C1-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40Alkylboron groups, C6-C 60 Arylboron group, phosphine oxide group, C1-C 40 Alkyl phosphine oxide group, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide groups, and C6-C 60 or they may be bonded to adjacent groups (e.g., adjacent R1, R2, a phenyl ring on one side of a carbazole group, etc.) to form a condensed ring. Specifically, R1 and R2 are each independently selected from the group consisting of hydrogen, deuterium (D), halogen, a cyano group, C1 to C 40 Alkyl groups of C6 to C 60 and heteroaryl groups having 5 to 60 ring atoms. In this case, the number of substituents of R1 and R2 is not particularly limited, and as an example, g and h are each independently an integer of 0 to 4. More specifically, R1 is a C6 to C 18 It is preferable that g is 1. The fused ring is an aryl group having a C3 to C 60 Condensed aliphatic rings (specifically, C3 to C 30 (condensed aliphatic rings), C6-C 60 Condensed aromatic rings (specifically, C6 to C 30 fused heteroaromatic rings having 5 to 60 members (specifically, fused heteroaromatic rings having 5 to 30 members), C3 to C 60 and combinations thereof, more specifically, one or more selected from the group consisting of C6 to C 30 may be a fused aromatic ring of the formula:

[0039] Furthermore, the second host according to the present invention may have a primary asymmetric structure in which an azine group (e.g., an X1-X3-containing heterocycle) and a carbazole group are linked directly or via a linker (L) to the azine group, and may have a secondary asymmetric structure in which an aryl group (e.g., an R3-containing ring) and a dibenzo-based moiety represented by the above [Chemical Formula 4] are bonded to the azine group at the center. When a dibenzo-based moiety represented by the above [Chemical Formula 4] is introduced into the second host, a dibenzo-based moiety such as a dibenzofuranyl group or a dibenzothiophenyl group may be excluded from the heteroaryl group of R1 and / or R2.

[0040] The X1 to X3-containing heterocycle and the carbazole group may be linked directly or via a linker (L). Such a linker may be a linker of a normal divalent group known in the art, and an example of such a linker is a C6 to C 60 and substituted or unsubstituted heteroarylene groups having 5 to 60 ring atoms. Specifically, L is selected from the group consisting of C6 to C 24 and a substituted or unsubstituted heteroarylene group having 5 to 18 ring atoms, and more specifically, may be phenylene, biphenylene, or terphenylene.

[0041] In one embodiment, L can be a single bond or a linker selected from the following structural formulas: [ka] In the above formula, * is a bonding site with the above [Chemical Formula 2]. Although not shown in the above structural formula, at least one substituent known in the art (for example, the same as the definition of R1 to R6) may be substituted.

[0042] In the above [Chemical Formula 2], the arylene group and heteroarylene group of L, and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, alkylphosphine oxide group, arylphosphine group, arylphosphine oxide group, arylamine group, and fused rings of R1 to R6 each independently represent deuterium (D), a halogen group, a cyano group, a nitro group, a C2 to C4 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 1 to 40 ring atoms, C1 to C 40 Alkyl groups of C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy groups, C6-C 60 Aryloxy groups, C1-C 40 Alkylsilyl groups, C6-C 60 Arylsilyl groups, C1-C 40 Alkylboron groups, C6-C 60 Arylboron groups, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide groups, and C6-C 60 and when there are a plurality of the above-mentioned substituents, they may be the same or different.

[0043] In one embodiment of the present invention, the second host represented by the above [Chemical Formula 2] may be embodied as the following [Chemical Formula 5] or [Chemical Formula 6] depending on the type of substituent introduced into the X1 to X3-containing heterocycle (e.g., an azine group). [ka] [ka] In the above formula, X1 to X3, Z, L, R1 to R5, g, h, i, j, k, and n are each as defined in [Chemical Formula 2] above.

[0044] In another embodiment of the present invention, the second host represented by [Formula 2] above may be embodied as any one of [Formula 7] to [Formula 10] below depending on the binding position of a substituent (e.g., R1) introduced into the carbazole group (Cz). [ka] [ka] [ka] [ka] In the above formula, X1 to X3, A, L, R1, R3, and i are each as defined in [Chemical Formula 2] above.

[0045] In one embodiment, R1 may be a substituent selected from the following structural formulas: [ka] In the above formula, * is a bonding site with the above [Chemical Formula 2].

[0046] In another embodiment of the present invention, the second host represented by [Formula 2] above may be embodied as any one of [Formula 11] to [Formula 17] below depending on the type of X1 to X3-containing heterocycle (e.g., azine group). [ka] [ka] [ka] [ka] [ka] [ka] [ka] In the above formula, Z, L, R1 to R5, g, h, i, j, k, and n are each as defined in [Chemical Formula 2] above.

[0047] The second host represented by [Chemical Formula 2] according to the present invention as described above can be embodied as the following compounds E-1 to E-10, but is not limited to these examples. [ka]

[0048] In the present invention, "alkyl" refers to a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.

[0049] In the present invention, "alkenyl" refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon double bonds. Examples of this include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, etc.

[0050] In the present invention, "alkynyl" refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon triple bonds. Examples of this include, but are not limited to, ethynyl, 2-propynyl, etc.

[0051] In the present invention, "cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples thereof include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

[0052] In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 ring atoms, in which one or more carbons, preferably 1 to 3 carbons, in the ring are substituted with a heteroatom such as N, O, S or Se. Examples include, but are not limited to, morpholine, piperazine, etc.

[0053] In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or a combination of two or more rings. The two or more rings may be in a pendant or condensed form. Examples of such groups include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

[0054] In the present invention, "heteroaryl" means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 ring atoms. In this case, one or more carbons, preferably 1 to 3 carbons, in the ring are substituted with a heteroatom such as N, O, S or Se. In addition, two or more rings may be in a pendant or condensed form, and further in a condensed form with an aryl group. Examples of this include, but are not limited to, 6-membered monocyclic rings such as pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, polycyclic rings such as phenoxathienyl, indoLizinyL, indolyl, purinyl, quinolyl, benzothiazoLe, carbazolyl, dibenzofuranyl, dibenzothiophenyL, and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.

[0055] In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O-, where R' is an alkyl group having 1 to 40 carbon atoms. Such alkyloxy may have a linear, branched, or cyclic structure. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

[0056] In the present invention, "aryloxy" refers to a monovalent substituent represented by RO-, where R means an aryl having 5 to 40 carbon atoms. Examples of this include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, etc.

[0057] In the present invention, "alkylsilyl" refers to silyl substituted with an alkyl having 1 to 40 carbon atoms, including not only mono- but also di- and tri-alkylsilyl, and "arylsilyl" refers to silyl substituted with an aryl having 5 to 60 carbon atoms, including not only mono- but also polyarylsilyl such as di- and tri-arylsilyl.

[0058] In the present invention, the term "alkylboron" refers to boron substituted with an alkyl group having 1 to 40 carbon atoms, and the term "arylboron" refers to boron substituted with an aryl group having 6 to 60 carbon atoms.

[0059] In the present invention, the term "alkylphosphinyl group" refers to a phosphine group substituted with an alkyl group having 1 to 40 carbon atoms, and includes not only mono- but also di-alkylphosphinyl groups. In addition, in the present invention, the term "arylphosphinyl group" refers to a phosphine group substituted with a monoaryl or diaryl group having 6 to 60 carbon atoms, and includes not only mono- but also di-arylphosphinyl groups.

[0060] In the present invention, the term "arylamine" means an amine substituted with an aryl having 6 to 60 carbon atoms, and includes not only mono- but also di-arylamines.

[0061] In the present invention, the term "heteroarylamine" means an amine substituted with a heteroaryl having 5 to 60 ring atoms, and includes not only mono- but also di-heteroarylamines.

[0062] In the present invention, the (aryl)(heteroaryl)amine means an amine substituted with an aryl having 6 to 60 carbon atoms and a heteroaryl having 5 to 60 ring atoms.

[0063] In the present invention, the term "fused ring" means a fused aliphatic ring having 3 to 40 carbon atoms, a fused aromatic ring having 6 to 60 carbon atoms, a fused heteroaliphatic ring having 3 to 60 ring atoms, a fused heteroaromatic ring having 5 to 60 ring atoms, a spiro ring having 3 to 60 carbon atoms, or a combination thereof.

[0064] In the above-mentioned composition for organic EL devices, the content ratio of the first host to the second host is 1:99 to 99:1 by weight, preferably 20:80 to 80:20 by weight, and more preferably 40:60 to 70:30 by weight. Within such a range, bipolar characteristics can be more effectively realized, and efficiency and life can be improved at the same time. In particular, in the present invention, when a P-type first host specialized in donor properties is mixed, the same or better effect can be obtained by using a relatively small amount compared to the amount of the existing P-type host.

[0065] The composition according to the present invention may further include a phosphorescent dopant. The phosphorescent dopant is a substance that emits light when mixed in a small amount with the first and second hosts, and is not particularly limited as long as it is a substance known in the art, and examples thereof include metal complex compounds containing iridium (Ir) or platinum (Pt). Such dopants can emit light by multiple excitation, which excites the dopant to a triplet or higher state.

[0066] The dopants are classified into red, green, and blue dopants, and any ordinary red, green, and blue dopants known in the art can be used without any particular limitation.

[0067] Specific examples of red dopants include, but are not limited to, PtOEP (Pt(II) octaporphine), 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 of these.

[0068] Examples of green dopants include, but are not limited to, Ir(ppy)3 (tris-(2-phenylpyridine)iridium), Ir(ppy)2(acac) (bis(2-phenylpyridine)(acetylacetonate)iridium(III)), Ir(mppy)3 (tris(2-4-tolyl)phenylpyridine)iridium), or a mixture of two or more of these.

[0069] Furthermore, examples of blue dopants include, but are not limited to, F2Irpic (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.

[0070] The content of the dopant as described above is not particularly limited, and is, for example, about 0 to 10% by weight, specifically about 0.1 to 10% by weight, and more specifically about 1 to 30% by weight, relative to the total weight of the composition.

[0071] <Organic EL element> An organic EL device according to one embodiment of the present invention includes an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, the one or more organic layers including the above-mentioned composition. As an example, the one or more organic layers include an emitting layer, and the above-mentioned composition is included as a host material of the emitting layer. As a result, the organic EL device of the present invention has low driving voltage, high efficiency, and long life characteristics, and can exhibit excellent phosphorescent emission characteristics.

[0072] Hereinafter, preferred embodiments of the organic EL device according to the present invention will be described with reference to the accompanying drawings. However, the embodiments of the present invention can be implemented in various modifications, and the scope of the present invention is not limited to the following embodiments. In order to avoid repetitive description, the components of the composition for organic EL devices described above will not be described.

[0073] FIG. 1 is a cross-sectional view that illustrates a schematic structure of an organic EL element according to an embodiment of the present invention.

[0074] As shown in Fig. 1, an organic electroluminescence device according to an embodiment of the present invention includes an anode 100 disposed on a substrate (not shown), a cathode 200 disposed opposite the anode, and one or more organic layers 300 between the anode 100 and the cathode 200, the one or more organic layers 300 including a hole transport region 310, an emitting layer 320, and an electron transport region. In this case, the emitting layer 320 includes the above-mentioned composition as a host. Optionally, the organic electroluminescence device according to the present invention may further include a capping layer (not shown) disposed on the cathode 200.

[0075] Each component of the organic EL element according to the present invention will be described in detail below.

[0076] (1) Anode In the organic EL device of the present invention, the anode 100 is mainly disposed on a substrate, electrically connected to a driving thin film transistor, and receives a driving current from the driving thin film transistor. The anode 100 is made of a material having a relatively high work function, and serves to inject holes into the organic layer 300, i.e., the hole transport region 310 (e.g., the hole injection layer 311).

[0077] The material for forming such an anode is not particularly limited, and may be any material commonly known in the art. For example, metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; 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.

[0078] The method for manufacturing the anode is not particularly limited and may be a common method in the art, for example, the anode may be formed by coating the anode material on a substrate by a known thin film forming method such as sputtering, ion plating, vacuum deposition, spin coating, etc.

[0079] The substrate is a plate-like member that supports the organic EL element, and examples thereof include, but are not limited to, a silicon wafer, quartz, a glass plate, a metal plate, a plastic film or sheet, and the like.

[0080] (2) Cathode In the organic EL device of the present invention, the cathode 200 is an electrode disposed opposite to the anode, specifically, disposed on the electron transport region 330. The cathode 200 is made of a material having a relatively low work function, and serves to inject electrons into an adjacent organic layer, i.e., the electron transport region 330 (e.g., the electron injection layer 332).

[0081] The material for forming such a cathode is not particularly limited, and may be any of those commonly known in the art, including, but not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin, and lead, and alloys thereof; and multilayered materials such as LiF / Al and LiO2 / Al.

[0082] The method for producing the cathode is not particularly limited, and can be produced by a common method in the art, like the anode. For example, the cathode material can be coated on one or more organic layers 300, specifically, the electron transport region, for example, the electron injection layer 332, by the thin film formation method described above.

[0083] (3)Organic layer In the organic EL device of the present invention, one or more organic layers 300 are disposed between the anode 100 and the cathode 200 and comprise a hole transport region 310 , a light emitting layer 320 , and an electron transport region 330 .

[0084] In one example, as shown in FIG. 1, the one or more organic layers 300 include a hole injection layer 311, a hole transport layer 312, an emissive layer 320, an electron transport layer 331, and an electron injection layer 332, disposed in sequence on the anode 100.

[0085] Each organic layer will now be described.

[0086] 1) Hole transport region In the organic EL device 100 of the present invention, the hole transport region 310 is a part of the organic layer 300 disposed on the anode 100 , and serves to transport holes injected from the anode 100 to the adjacent light emitting layer 320 .

[0087] Such a hole transport region 310 includes one or more layers selected from the group consisting of a hole injection layer 311 and a hole transport layer 312. In this case, in consideration of the characteristics of the organic EL device, it is preferable to include both the hole injection layer 31 and the hole transport layer 32. As an example, the hole transport region 310 includes a hole injection layer 311 and a hole transport layer 312 sequentially stacked on the anode 100 as shown in FIG.

[0088] The materials for forming the hole injection layer 311 and the hole transport layer 312 are not particularly limited as long as they have a low hole injection barrier and a high hole mobility, and any hole injection layer / transport layer materials used in the relevant field can be used without limitation. The materials for forming the hole injection layer 311 and the hole transport layer 312 may be the same or different from each other.

[0089] Specifically, the hole injection layer 311 includes a hole injection material known in the art. Examples of the hole injection material include phthalocyanine compounds such as copper phthalocyanine; DNTPD (N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine), m-MTDATA (4,4',4"-tris(3-methylphenylphenylamino)triphenylamine), TDATA (4,4',4"-tris(N,N-diphenylamino)triphenylamine), 2TNATA (4,4',4"-tris{N,-(2- naphthyl)-N-phenylamino}-triphenylamine), PEDOT / PSS (poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate)), PANI / DBSA (polyaniline / dodecylbenzenesulfonic acid), PANI / CSA (polyaniline / camphorsulfonic acid), PANI / PSS (polyaniline) / poly(4-styrenesulfonate), etc., but are not limited thereto. These may be used alone or in combination of two or more.

[0090] The hole transport 312 comprises a hole transport material known in the art. Examples of the hole transport material include, but are not limited to, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole; fluorene derivatives; amine derivatives; triphenylamine derivatives such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine) and TCTA (4,4'-4"-tris(N-carbazolyl)triphenylamine); NPB (N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine) and TAPC (4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)benzeneamine]). These may be used alone or in combination of two or more.

[0091] The hole transport region 310 can be manufactured by a conventional method in the art, such as, but not limited to, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0092] 2) Light-emitting layer In the organic EL device of the present invention, the light-emitting layer 320 is a part of the organic layer 300 interposed between the anode 100 and the cathode 200, and specifically, is disposed on the hole transport region 320. As shown in FIG. 1, the light-emitting layer 320 may be disposed on the hole transport layer 312.

[0093] The light-emitting layer 320 is a layer in which holes and electrons injected from the anode and cathode, respectively, combine to form excitons. The color of the light emitted by the organic EL element changes depending on the material from which the light-emitting layer 320 is formed.

[0094] The light-emitting layer 320 according to the present invention includes a composition containing a first host represented by the above [Chemical Formula 1] and a second host represented by the above [Chemical Formula 2]. The above composition may optionally further contain a phosphorescent dopant. By including such a composition as the light-emitting layer 320 material, the organic EL device of the present invention can exhibit excellent phosphorescent emission characteristics while having low driving voltage, high efficiency, and long life characteristics.

[0095] The light-emitting layer 320 according to 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. In one example, it may be a light-emitting layer including a green phosphorescent material.

[0096] The light-emitting layer 320 may include a single layer made of one kind of material, a single layer made of a plurality of different materials, or two or more layers made of different materials. When the light-emitting layer 320 is made of a plurality of layers, the organic EL element can emit light of various colors. Specifically, the present invention can provide an organic EL element having a plurality of light-emitting layers made of different materials in series, which exhibits a mixed color. When the organic EL element is made of a plurality of light-emitting layers, the driving voltage of the element increases, but the current value in the organic EL element becomes constant, and an organic EL element with improved luminous efficiency can be provided according to the number of light-emitting layers.

[0097] Although not shown, the organic EL device 100 of the present invention may include multiple light-emitting stacks (not shown) each including at least one light-emitting layer.

[0098] The plurality of light-emitting layers included in such a light-emitting stack may be light-emitting layers that emit light of different colors or light of the same color. That is, the emission color changes depending on the material that constitutes the light-emitting layer. As an example, the plurality of light-emitting stacks include materials that emit blue, green, red, yellow, white, etc., and are formed using phosphorescent or fluorescent materials. In this case, the colors exhibited by each light-emitting layer may be complementary to each other. In addition, colors may be selected as a combination of colors that emit white. Each of such light-emitting layers may include a phosphorescent or fluorescent dopant that corresponds to the selected color.

[0099] Although not shown, the organic EL device 100 of the present invention may further include a charge generation layer (CGL) (not shown) disposed between and connecting adjacent stacks among the multiple light-emitting stacks.

[0100] The charge generation layer (CGL) refers to a layer that does not directly contact two electrodes (e.g., anode, cathode) in an organic EL device having a plurality of light-emitting stacks and separates adjacently arranged light-emitting stacks. Such a charge generation layer is disposed between two adjacent light-emitting stacks and serves as a cathode that generates and supplies electrons to one light-emitting stack and serves as an anode that generates and supplies holes to the other light-emitting stack. As such a charge generation layer, any charge generation layer material known in the art can be used without limitation. In addition, the charge generation layer material may be doped with a conventional n-type material and / or p-type material known in the art.

[0101] The light-emitting layer 320 may be manufactured by a conventional method in the art. Examples include, but are not limited to, vacuum deposition, spin coating, casting, LB method, inkjet printing, laser printing, and laser thermal transfer (LITI). For example, the light-emitting layer may be formed by co-deposition of a first host represented by [Chemical Formula 1] and a second host represented by [Chemical Formula 2]. In this case, a dopant may also be co-deposited.

[0102] 3)Electron transport region In the organic EL device according to the present invention, the electron transport region 330 is an organic layer disposed on the light emitting layer 320 , and transports electrons injected from the cathode 200 to the light emitting layer 320 .

[0103] The electron transport region 330 includes at least one layer selected from the group consisting of an electron transport layer 331 and an electron injection layer 332 .

[0104] As an example, the electron transport region 330 includes an electron transport layer 331 and an electron injection layer 332 sequentially stacked on the light emitting layer 320 as shown in FIG.

[0105] In the electron transport region 330 according to the present invention, the electron transport layer 331 may be made of any electron transport material that is easy to inject electrons into and has a large electron mobility, without any particular limitations. Examples of such electron transport materials include, but are not limited to, oxazole-based compounds, isoxazole-based compounds, triazole-based compounds, isothiazole-based compounds, oxadiazole-based compounds, thiadiazole-based compounds, perylene-based compounds, aluminum complexes (e.g., Alq3 (tris(8-quinolinolato)-aluminum), BAlq, SAlq, Alph3, Almq3), and gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)). These may be used alone or in combination of two or more.

[0106] Furthermore, the electron injection layer 332 may be made of any electron injection material that is easy to inject electrons into and has a large electron mobility, without any particular limitations. Examples of the electron injection material include, but are not limited to, LiF, Li2O, BaO, NaCl, CsF, lanthanum metals such as Yb, and metal halides such as RbCl and RbI. These may be used alone or in combination of two or more.

[0107] The electron transport region 330 according to the present invention, specifically the electron transport layer 331 and / or the electron injection layer 332, may be co-deposited with an n-type dopant so that electrons can be easily injected from the cathode 200. In this case, the n-type dopant may be any alkali metal complex compound known in the art, and examples thereof include alkali metals, alkaline earth metals, and rare earth metals.

[0108] The electron transport region 330 can be manufactured by a method commonly used in the art, such as, but not limited to, vacuum deposition, spin coating, casting, LB method, inkjet printing, laser printing, and laser thermal transfer (LITI).

[0109] 4) Light-emitting auxiliary layer Although not shown, the organic EL device 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 .

[0110] The light-emitting auxiliary layer transports holes from the hole transport region 310 to the light-emitting layer 320, or blocks the movement of electrons and / or excitons, thereby adjusting the thickness of the organic layer 300. In particular, the light-emitting auxiliary layer has a high LUMO value and therefore blocks the movement of electrons to the hole transport layer 32, and also has a high triplet energy and therefore blocks the diffusion of excitons from the light-emitting layer 40 to the hole transport layer 32.

[0111] The light-emitting auxiliary layer includes a hole-transporting material and may be made of the same material as the hole-transporting region. The light-emitting auxiliary layers of the red, green, and blue organic light-emitting devices may be made of the same material.

[0112] The light-emitting auxiliary layer material is not particularly limited, and examples thereof include carbazole derivatives and arylamine derivatives. Specific examples include, but are not limited to, NPD (N,N-dinaphthyl-N,N'-diphenylbenzidine), TPD (N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-benzidine), s-TAD, and MTDATA (4,4',4"-tris(N-3-methylphenyl-N-phenyl-amino)-triphenylamine). These may be used alone or in combination of two or more.

[0113] In addition, the light-emitting auxiliary layer may contain a p-type dopant in addition to the above-mentioned materials. As the p-type dopant, any p-type dopant known in the art may be used without any particular limitation. In this case, the content of the p-type dopant may be appropriately adjusted within a range known in the art, and may be, for example, about 0.5 to 50 parts by weight with respect to 100 parts by weight of the hole transport material.

[0114] The light-emitting auxiliary layer can be formed by a method well known in the art, such as vacuum deposition, spin coating, casting, LB method, inkjet printing, laser printing, and laser thermal transfer (LITI), but is not limited to these.

[0115] 5) Hole blocking layer Although not shown, the organic EL device 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 .

[0116] The hole blocking layer 333 prevents excitons or holes generated in the light emitting layer 320 from diffusing (moving) to the electron transport layer 331, thereby improving the life of the organic EL element.

[0117] As the material for such a hole blocking layer, any substance having normal electron transport properties known in the art can be used without any particular limitation. Examples of such a material include BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) and BAlq (bis(2-methyl-8-quinolinolato)(4-phenyl-phenolato)aluminum(III).

[0118] The hole blocking layer can be formed by a method well known in the art, such as vacuum deposition, spin coating, casting, LB method, inkjet printing, laser printing, laser thermal transfer (LITI), etc., but is not limited to these.

[0119] (4) Capping layer Optionally, the organic EL device 100 of the present invention may further include a capping layer (not shown) disposed on the cathode 200 .

[0120] The capping layer protects the organic EL device and also helps the light emitted from the organic layer to be efficiently emitted to the outside.

[0121] As the capping layer, at least one selected from the group consisting of tris-8-hydroxyquinoline aluminum (Alq3), ZnSe, 2,5-bis(6'-(2',2"-bipyridyl))-1,1-dimethyl-3,4-diphenylsilole, 4'-bis[N-(1-naphthyl)-N-phenyl-amino]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) can be used. Such a material for forming the capping layer is less expensive than the materials for forming other layers of the organic light-emitting device.

[0122] Such a capping layer may be a single layer, but may also include two or more layers having different refractive indices such that the refractive index changes gradually through the two or more layers.

[0123] The capping layer can be produced by various methods commonly used in the art, such as vacuum deposition, spin coating, casting, or the LB method.

[0124] The organic EL device according to the present invention has a structure in which an anode 100, an organic layer 300, and a cathode 200 are sequentially stacked. If necessary, an insulating layer (not shown) or an adhesive layer (not shown) may be further included between the anode 100 and the organic layer 300, or between the cathode 200 and the organic layer 300. When a voltage, a current, or both are applied, the organic EL device according to the present invention has an increased half-life time of initial luminance while maintaining maximum luminous efficiency, thereby providing excellent life characteristics.

[0125] The organic EL device of the present invention described above can be manufactured by a conventional method in the art. For example, an anode material is vacuum-deposited on a substrate, and then a hole transport region material, a light-emitting layer material, an electron transport region material, and a cathode material are vacuum-deposited on the anode in this order to manufacture the organic EL device. EXAMPLES

[0126] The present invention will be described in detail below with reference to examples. However, the examples described below are merely illustrative of the present invention, and the present invention is not limited to these examples.

[0127] [Example of synthesis of the first host] <Preparation Example 1-1> Synthesis of Cz-D1 [ka] Under a nitrogen stream, 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. After the reaction was completed, the mixture was extracted with ethyl acetate, water was removed with MgSO4, and the mixture was purified by column chromatography (hexane:EA=5:1 (v / v)) to obtain Cz-D1 (125.7 g, yield 72%). Mass (theoretical value: 329.25, measured value: 329 g / mol)

[0128] <Preparation Example 1-2> Synthesis of Cz-D2 [ka] The target compound Cz-D2 (135.5 g, 63% yield) was obtained in the same manner as in Preparation Example 1-1 above, except that 4-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0129] <Preparation Example 1-3> Synthesis of Cz-D3 [ka] The target compound Cz-D3 (148.4 g, 69% yield) was obtained in the same manner as in Preparation Example 1-1 above, except that 3-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0130] <Preparation Example 1-4> Synthesis of Cz-D4 [ka] The target compound Cz-D4 (96.8 g, 45% yield) was obtained in the same manner as in Preparation Example 1-1 above, except that 2-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0131] <Preparation Example 2-1> Synthesis of Cz-D5 [ka] The target compound Cz-D5 (117.1 g, yield 67%) was obtained in the same manner as in Preparation Example 1-1 above, 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. Mass (theoretical value: 329.25, measured value: 329 g / mol)

[0132] <Preparation Example 2-2> Synthesis of Cz-D6 [ka] The target compound Cz-D6 (139.8 g, 65% yield) was obtained in the same manner as in Preparation Example 2-1 above, except that 4-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0133] <Preparation Example 2-3> Synthesis of Cz-D7 [ka] The target compound Cz-D7 (152.7 g, 71% yield) was obtained in the same manner as in Preparation Example 2-1 above, except that 3-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0134] <Preparation Example 2-4> Synthesis of Cz-D8 [ka] The target compound Cz-D8 (75.2 g, 35% yield) was obtained in the same manner as in Preparation Example 2-1 above, except that 2-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0135] <Preparation Example 3-1> Synthesis of Cz-D9 [ka] The target compound Cz-D9 (134.5 g, 77% yield) was obtained in the same manner as in Preparation Example 1-1 above, 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. Mass (theoretical value: 329.25, measured value: 329 g / mol)

[0136] <Preparation Example 3-2> Synthesis of Cz-D10 [ka] The target compound Cz-D10 (159.1 g, 74% yield) was obtained in the same manner as in Preparation Example 3-1 above, except that 4-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0137] <Preparation Example 3-3> Synthesis of Cz-D11 [ka] The target compound Cz-D11 (163.4 g, 76% yield) was obtained in the same manner as in Preparation Example 3-1 above, except that 3-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0138] <Preparation Example 3-4> Synthesis of Cz-D12 [ka] The target compound Cz-D12 (92.4 g, 43% yield) was obtained in the same manner as in Preparation Example 3-1 above, except that 2-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0139] <Preparation Example 4-1> Synthesis of Cz-D13 [ka] The target compound Cz-D13 (94.3 g, 54% yield) was obtained in the same manner as in Preparation Example 1-1 above, 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. Mass (theoretical value: 329.25, measured value: 329 g / mol)

[0140] <Preparation Example 4-2> Synthesis of Cz-D14 [ka] The target compound Cz-D14 (122.6 g, 57% yield) was obtained in the same manner as in Preparation Example 4-1 above, except that 4-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0141] <Preparation Example 4-3> Synthesis of Cz-D15 [ka] The target compound Cz-D15 (111.8 g, 52% yield) was obtained in the same manner as in Preparation Example 4-1 above, except that 3-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0142] <Preparation Example 4-4> Synthesis of Cz-D16 [ka] The target compound Cz-D16 (68.8 g, 32% yield) was obtained in the same manner as in Preparation Example 4-1 above, except that 2-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0143] <Preparation Example 5-1> Synthesis of BCz-D1 <Step 5-1-1> Synthesis of 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7 [ka] Under a nitrogen stream, Cz-D1 (100.0 g, 303.7 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(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.

[0144] After the reaction was completed, the mixture was extracted with ethyl acetate, water was removed with MgSO4, and the mixture was purified by column chromatography (hexane:EA=8:1 (v / v)) to obtain 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7 (96.0 g, yield 84%). Mass (theoretical value: 376.3, measured value: 376 g / mol)

[0145] <Preparation Example 5-1-2> Synthesis of BCz-D1 [ka] Under a nitrogen stream, 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-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 mixed and stirred at 120°C for 4 hours.

[0146] After the reaction was completed, the mixture was extracted with methylene chloride, and filtered by adding MgSO4. After removing the solvent from the obtained organic layer, the mixture was purified by column chromatography (hexane:EA=7:1(v / v)) to obtain BCz-D1 (71.1 g, yield 66%). Mass (theoretical value: 422.59, measured value: 422 g / mol)

[0147] <Preparation Example 5-2> Synthesis of BCz-D2 [ka] The target compound BCz-D2 (66.4 g, final yield 54.0%) was obtained in the same manner as in Preparation Example 5-1 above, except that Cz-D2 (100 g, 246.7 mmol) was used instead of Cz-D1. Mass (theoretical value: 498.69, measured value: 498 g / mol)

[0148] <Preparation Example 5-3> Synthesis of BCz-D3 [ka] The target compound BCz-D3 (59.7 g, final yield 48.5%) was obtained in the same manner as in Preparation Example 5-1 above, except that Cz-D3 (100 g, 246.7 mmol) was used instead of Cz-D1. Mass (theoretical value: 498.69, measured value: 498 g / mol)

[0149] <Preparation Example 5-4> Synthesis of BCz-D4 [ka] The target compound BCz-D4 (59.4 g, final yield 48.3%) was obtained in the same manner as in Preparation Example 5-1 above, except that Cz-D4 (100 g, 246.7 mmol) was used instead of Cz-D1. Mass (theoretical value: 498.69, measured value: 498 g / mol)

[0150] [Synthesis Example 1] Synthesis of A-1 [ka] Under a nitrogen stream, BCz-D1 (10.0 g, 23.6 mmol), Cz-D1 (9.3 g, 28.3 mmol), 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 was completed, the toluene was concentrated, and the solid salt was filtered and purified by recrystallization to obtain the target compound A-1 (13.0 g, 82% yield). Mass (theoretical value: 670.93, measured value: 670g / mol)

[0151] [Synthesis Example 2] Synthesis of A-2 [ka] The target compound A-2 (13.8 g, 78% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D2 (100 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0152] [Synthesis Example 3] Synthesis of A-3 [ka] The target compound A-3 (13.2 g, 75% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D3 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0153] [Synthesis Example 4] Synthesis of A-4 [ka] The target compound A-4 (12.2 g, 69% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D4 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0154] [Synthesis Example 5] Synthesis of A-5 [ka] The target compound A-5 (8.73 g, 55% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D5 (9.3 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 670.93, measured value: 670g / mol)

[0155] [Synthesis Example 6] Synthesis of A-6 [ka] The target compound A-6 (7.42 g, 42% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D6 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0156] [Synthesis Example 7] Synthesis of A-7 [ka] The target compound A-7 (8.83 g, 50% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D7 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0157] [Synthesis Example 8] Synthesis of A-8 [ka] The target compound A-8 (9.89 g, 56% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D8 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0158] [Synthesis Example 9] Synthesis of A-9 [ka] The target compound A-9 (8.41 g, 53% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D9 (9.3 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 670.93, measured value: 670g / mol)

[0159] [Synthesis Example 10] Synthesis of A-10 [ka] The target compound A-10 (8.66 g, 49% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D10 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0160] [Synthesis Example 11] Synthesis of A-11 [ka] The target compound A-11 (9.01 g, 51% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D11 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0161] [Synthesis Example 12] Synthesis of A-12 [ka] The target compound A-12 (9.19 g, 52% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D12 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0162] [Synthesis Example 13] Synthesis of A-13 [ka] The target compound A-13 (9.52 g, 60% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D13 (9.3 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 670.93, measured value: 670g / mol)

[0163] [Synthesis Example 14] Synthesis of A-14 [ka] The target compound A-14 (10.78 g, 61% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D14 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0164] [Synthesis Example 15] Synthesis of A-15 [ka] The target compound A-15 (11.13 g, 63% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D15 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0165] [Synthesis Example 16] Synthesis of A-16 [ka] The target compound A-16 (9.02 g, 51% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D16 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0166] [Synthesis Example 17] Synthesis of B-1 [ka] Under a nitrogen stream, BCz-D2 (10.0 g, 20.1 mmol), Cz-D1 (7.9 g, 24.1 mmol), 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 was completed, the toluene was concentrated, and the solid salt was filtered and purified by recrystallization to obtain the target compound B-1 (10.2 g, 62% yield). Mass (theoretical value: 747.02, measured value: 747g / mol)

[0167] [Synthesis Example 18] Synthesis of B-2 [ka] The target compound B-2 (8.5 g, 48% yield) was obtained in the same manner as in Synthesis Example 17 above, except that Cz-D5 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0168] [Synthesis Example 19] Synthesis of B-3 [ka] The target compound B-3 (11.1 g, 63% yield) was obtained in the same manner as in Synthesis Example 17 above, except that Cz-D9 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0169] [Synthesis Example 20] Synthesis of B-4 [ka] The target compound B-4 (7.42 g, 42% yield) was obtained in the same manner as in Synthesis Example 17 above, except that Cz-D13 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0170] [Synthesis Example 21] Synthesis of C-1 [ka] Under a nitrogen stream, BCz-D3 (10.0 g, 20.1 mmol), Cz-D1 (7.9 g, 24.1 mmol), 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 was completed, the toluene was concentrated, and the solid salt was filtered and purified by recrystallization to obtain the target compound C-1 (9.4 g, 63% yield). Mass (theoretical value: 747.02, measured value: 747g / mol)

[0171] [Synthesis Example 22] Synthesis of C-2 [ka] The target compound C-2 (7.78 g, 44% yield) was obtained in the same manner as in Synthesis Example 21 above, except that Cz-D5 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0172] [Synthesis Example 23] Synthesis of C-3 [ka] The target compound C-3 (11.67 g, 66% yield) was obtained in the same manner as in Synthesis Example 21 above, except that Cz-D9 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0173] [Synthesis Example 24] Synthesis of C-4 [ka] The target compound C-4 (6.89 g, 39% yield) was obtained in the same manner as in Synthesis Example 21 above, except that Cz-D13 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0174] [Synthesis Example 25] Synthesis of D-1 [ka] Under a nitrogen stream, BCz-D4 (10.0 g, 20.1 mmol), Cz-D1 (7.9 g, 24.1 mmol), 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 was completed, the toluene was concentrated, and the solid salt was filtered and purified by recrystallization to obtain the target compound D-1 (8.1 g, 54% yield). Mass (theoretical value: 747.02, measured value: 747g / mol)

[0175] [Synthesis Example 26] Synthesis of D-2 [ka] The target compound D-2 (7.24 g, 41% yield) was obtained in the same manner as in Synthesis Example 25 above, except that Cz-D5 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0176] [Synthesis Example 27] Synthesis of D-3 [ka] The target compound D-3 (8.41 g, 51% yield) was obtained in the same manner as in Synthesis Example 25 above, except that Cz-D9 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0177] [Synthesis Example 28] Synthesis of D-4 [ka] The target compound D-4 (5.47 g, 31% yield) was obtained in the same manner as in Synthesis Example 25 above, except that Cz-D13 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0178] [Example of synthesis of the second host] [Preparation Example 6] Synthesis of ACz-1 [ka] Under a nitrogen stream, 3-bromo-9H-carbazole (100.0 g, 406.3 mmol), 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (99.5 g, 487.6 mmol), Pd(PPh3)4 (23.5 g, 20.3 mmol), K2CO3 (140.4 g, 1,015.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0179] After the reaction was completed, the mixture was extracted with methylene chloride, and filtered by adding MgSO4. After removing the solvent from the obtained organic layer, the mixture was purified by column chromatography (hexane:DCM=9:1 (v / v)) to obtain ACz-1 (64.3 g, yield 65%). Mass (theoretical value: 243.31, measured value: 243 g / mol)

[0180] [Preparation Example 7] Synthesis of ACz-2 [ka] Under a nitrogen stream, 3-bromo-9H-carbazole (100.0 g, 406.3 mmol), 2-([1,1':3',1"-terphenyl]-5'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (173.7 g, 487.6 mmol), Pd(PPh3)4 (23.5 g, 20.3 mmol), K2CO3 (140.4 g, 1,015.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0181] After the reaction was completed, the mixture was extracted with methylene chloride, and filtered by adding MgSO4. After removing the solvent from the obtained organic layer, the mixture was purified by column chromatography (hexane:DCM=9:1 (v / v)) to obtain ACz-2 (82.0 g, yield 51%). Mass (theoretical value: 395.51, measured value: 395 g / mol)

[0182] [Preparation Example 8] Synthesis of ACz-3 [ka] Under a nitrogen stream, 3-bromo-9H-carbazole (100.0 g, 406.3 mmol), 2-([1,1':4',1"-terphenyl]-2'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (173.7 g, 487.6 mmol), Pd(PPh3)4 (23.5 g, 20.3 mmol), K2CO3 (140.4 g, 1,015.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0183] After the reaction was completed, the mixture was extracted with methylene chloride, and filtered by adding MgSO4. After removing the solvent from the obtained organic layer, the mixture was purified by column chromatography (hexane:DCM=9:1 (v / v)) to obtain ACz-3 (70.7 g, yield 44%). Mass (theoretical value: 395.51, measured value: 395 g / mol)

[0184] [Preparation Example 9] Synthesis of ACz-4 [ka] Under a nitrogen stream, 2-bromo-9H-carbazole (100.0 g, 406.3 mmol), 2-([1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (136.6 g, 487.6 mmol), Pd(PPh3)4 (23.5 g, 20.3 mmol), K2CO3 (140.4 g, 1,015.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0185] After the reaction was completed, the mixture was extracted with methylene chloride, and filtered by adding MgSO4. After removing the solvent from the obtained organic layer, the mixture was purified by column chromatography (hexane:DCM=9:1 (v / v)) to obtain ACz-4 (85.7 g, yield 66%). Mass (theoretical value: 319.41, measured value: 319 g / mol)

[0186] [Preparation Example 10] Synthesis of ACz-5 [ka] Under a nitrogen stream, 2-bromo-9H-carbazole (100.0 g, 406.3 mmol), 2-([1,1':3',1"-terphenyl]-5'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (173.7 g, 487.6 mmol), Pd(PPh3)4 (23.5 g, 20.3 mmol), K2CO3 (140.4 g, 1,015.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0187] After the reaction was completed, the mixture was extracted with methylene chloride, and filtered by adding MgSO4. After removing the solvent from the obtained organic layer, the mixture was purified by column chromatography (hexane:DCM=9:1 (v / v)) to obtain ACz-5 (83.6 g, yield 52%). Mass (theoretical value: 395.51, measured value: 395 g / mol)

[0188] [Preparation Example 11] Synthesis of ACz-6 [ka] Under a nitrogen stream, 2-bromo-9H-carbazole (100.0 g, 406.3 mmol), 2-([1,1':4',1"-terphenyl]-2'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (173.7 g, 487.6 mmol), Pd(PPh3)4 (23.5 g, 20.3 mmol), K2CO3 (140.4 g, 1,015.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0189] After the reaction was completed, the mixture was extracted with methylene chloride, and filtered by adding MgSO4. After removing the solvent from the obtained organic layer, the mixture was purified by column chromatography (hexane:DCM=9:1 (v / v)) to obtain ACz-6 (65.9 g, yield 41%). Mass (theoretical value: 395.51, measured value: 395 g / mol)

[0190] [Synthesis Example 29] Synthesis of E-1 [ka] Under a nitrogen stream, ACz-1 (10.0 g, 41.1 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (17.6 g, 49.3 mmol), Pd(OAc)2 (2.37 g, 2.1 mmol), P(t-Bu)3 (1.0 ml, 4.1 mmol), NaO(t-Bu) (7.9 g, 82.2 mmol), and toluene (100 ml) were mixed and stirred at 110 ° C for 5 hours. After the reaction was completed, the toluene was concentrated, the solid salt was filtered, and the product was purified by recrystallization to obtain the target compound E-1 (14.9 g, 64% yield). Mass (theoretical value: 564.65, measured value: 564 g / mol)

[0191] [Synthesis Example 30] Synthesis of E-2 [ka] The target compound E-2 (16.1 g, 61% yield) was obtained in the same manner as in Synthesis Example 29 above, except that 2-(3-bromophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (23.6 g, 49.3 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine. Mass (theoretical value: 640.75, measured value: 640g / mol)

[0192] [Synthesis Example 31] Synthesis of E-3 [ka] The target compound E-3 (19.4 g, 67% yield) was obtained in the same manner as in Synthesis Example 29 above, except that 2-([1,1'-biphenyl]-3-yl)-4-([1,1'-biphenyl]-4-yl)-6-(3-bromophenyl)-1,3,5-triazine (26.7 g, 49.3 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine. Mass (theoretical value: 702.86, measured value: 702 g / mol)

[0193] [Synthesis Example 32] Synthesis of E-4 [ka] Under a nitrogen stream, ACz-2 (10.0 g, 25.3 mmol), 2-(3-bromophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (14.5 g, 30.3 mmol), Pd(OAc)2 (1.5 g, 1.3 mmol), P(t-Bu)3 (0.6 ml, 2.5 mmol), NaO(t-Bu) (4.9 g, 50.6 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, the solid salt was filtered, and the product was purified by recrystallization to obtain the target compound E-4 (10.4 g, 52% yield). Mass (theoretical value: 792.94, measured value: 792 g / mol)

[0194] [Synthesis Example 33] Synthesis of E-5 [ka] The target compound E-5 (9.6 g, 48% yield) was obtained in the same manner as in Synthesis Example 32 above, except that ACz-3 (10.0 g, 25.3 mmol) was used instead of ACz-2 (10.0 g, 25.3 mmol). Mass (theoretical value: 792.94, measured value: 792 g / mol)

[0195] [Synthesis Example 34] Synthesis of E-6 [ka] Under a nitrogen stream, ACz-4 (10.0 g, 31.3 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (13.4 g, 37.6 mmol), Pd(OAc)2 (1.8 g, 1.6 mmol), P(t-Bu)3 (0.8 ml, 3.1 mmol), NaO(t-Bu) (6.0 g, 62.6 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, the solid salt was filtered, and the product was purified by recrystallization to obtain the target compound E-6 (10.2 g, 51% yield). Mass (theoretical value: 640.75, measured value: 640g / mol)

[0196] [Synthesis Example 35] Synthesis of E-7 [ka] The target compound E-7 (11.9 g, 53% yield) was obtained in the same manner as in Synthesis Example 34 above, except that 2-(3-bromophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (18.0 g, 37.6 mmol) was used instead of 2-chloro-(4-dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine. Mass (theoretical value: 716.84, measured value: 716 g / mol)

[0197] [Synthesis Example 36] Synthesis of E-8 [ka] The target compound E-8 (9.9 g, 44% yield) was obtained in the same manner as in Synthesis Example 34 above, except that 2-(3-bromophenyl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (18.0 g, 37.6 mmol) was used instead of 2-chloro-(4-dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine. Mass (theoretical value: 716.84, measured value: 716 g / mol)

[0198] [Synthesis Example 37] Synthesis of E-9 [ka] Under a nitrogen stream, ACz-5 (10.0 g, 25.3 mmol), 2-(3-bromophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (14.5 g, 30.3 mmol), Pd(OAc)2 (1.5 g, 1.3 mmol), P(t-Bu)3 (0.6 ml, 2.5 mmol), NaO(t-Bu) (4.9 g, 50.6 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, the solid salt was filtered, and the product was purified by recrystallization to obtain the target compound E-9 (9.2 g, 46% yield). Mass (theoretical value: 792.94, measured value: 792 g / mol)

[0199] [Synthesis Example 38] Synthesis of E-10 [ka] The target compound E-10 (7.8 g, 39% yield) was obtained in the same manner as in Synthesis Example 37 above, except that ACz-6 (10.0 g, 25.3 mmol) was used instead of ACz-5 (10.0 g, 25.3 mmol). Mass (theoretical value: 792.94, measured value: 792 g / mol)

[0200] [Example 1] Fabrication of green organic EL element Compound A-1 synthesized in Synthesis Example 1 and compound E-1 synthesized in Synthesis Example 29 were purified by sublimation to high purity by a conventional method, and then green organic EL devices were fabricated according to the following process.

[0201] First, a glass substrate coated with a thin film of ITO (Indium Tin Oxide) at a thickness of 1500 Å was ultrasonically cleaned with distilled water. After cleaning with distilled water, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, and the substrate was then dried and transferred to a UV ozone cleaner (Power sonic 405, manufactured by Fashintech Co., Ltd.) where it was cleaned with UV for 5 minutes and then transferred to a vacuum deposition machine.

[0202] On the ITO transparent electrode thus prepared, the following layers were stacked in the order of HT+2% PA(100Å) / HT(1200Å) / HA(300Å) / 60wt% compound A-1+30wt% compound E-1+10wt% Ir(ppy)3(400Å) / EA(50Å) / ET+LiQ(300Å_1:1 molar ratio) / LiF(10Å) / Al(1000Å) to fabricate an organic EL device.

[0203] The structures of HT, PA, HA, EA, ET, and Ir(ppy)3 used at this time are as follows: [ka]

[0204] [Examples 2 to 280] Fabrication of green organic EL element Green organic EL devices were produced in the same manner as in Example 1 above, except that compounds A-2 to D-4 synthesized in Synthesis Examples 2 to 28 were used instead of compound A-1 as the emitting host material, and compounds E-2 to E-10 synthesized in Synthesis Examples 30 to 38 were used instead of compound E-1 (see Table 1 below).

[0205] [Comparative Example 1] Fabrication of green organic EL element A green organic EL device was fabricated in the same manner as in Example 1, except that HT-1 and ET-1 were used as the emitting host material instead of compounds A-1 and E-1. The structures of compounds HT-1 and ET-1 used in Comparative Example 1 are as follows. [ka]

[0206] [Comparative Example 2] Fabrication of green organic EL element A green organic EL device was produced in the same manner as in Example 1 above, except that compounds A-1 and ET-1 were used as the light-emitting host material instead of compounds A-1 and E-1.

[0207] [Comparative Example 3] Fabrication of green organic EL element A green organic EL device was fabricated in the same manner as in Example 1, except that compounds B-2 and ET-2 were used as the emitting host materials instead of compounds A-1 and E-1. The structure of compound ET-2 used in Comparative Example 3 is as follows. [ka]

[0208] [Comparative Example 4] Fabrication of green organic EL element A green organic EL device was fabricated in the same manner as in Example 1, except that compounds C-3 and ET-3 were used as the emitting host materials instead of compounds A-1 and E-1. The structure of compound ET-3 used in Comparative Example 4 is as follows. [ka]

[0209] [Comparative Example 5] Fabrication of green organic EL element A green organic EL device was fabricated in the same manner as in Example 1, except that compounds D-4 and ET-4 were used as the emitting host materials instead of compounds A-1 and E-1. The structure of compound ET-4 used in Comparative Example 5 is as follows. [ka]

[0210] [Evaluation example 1] For the green organic EL devices fabricated in Examples 1 to 280 and Comparative Examples 1 to 5, a current density of 10 mA / cm 2 The driving voltage, current efficiency, emission peak, and lifetime were measured at 1000 Hz, and the results are shown in Table 1 below.

[0211] [Table 1] JPEG2025515172000103.jpg251162JPEG2025515172000104.jpg252165JPEG2025515172000105.jpg252163JPEG20255151720 00106.jpg252166JPEG2025515172000107.jpg252168JPEG2025515172000108.jpg252169JPEG2025515172000109.jpg200170

[0212] As shown in Table 1 above, the green organic EL devices obtained in Examples 1 to 280 using a combination of a first host and a second host (A-1 to E-10) according to the present invention as emitting layer materials were confirmed to have better performance in terms of device efficiency, driving voltage, and life characteristics than the green organic EL device obtained in Comparative Example 1 using conventional HT-1 and ET-1. Also, the green organic EL devices obtained in Examples 1 to 280 of the present invention exhibited better efficiency and driving voltage characteristics than the green organic EL devices obtained in Comparative Examples 2 to 5 using a combination of the first host having excellent donor properties and an existing N-type host, and were confirmed to be significantly improved in terms of device life characteristics in particular.

Claims

1. A first host represented by the following [Chemical Formula 1], and A second host represented by the following [Chemical Formula 2]: A composition for an organic electroluminescence device comprising: 【Chemistry 1】 【Chemistry 2】 During the ceremony, Ar １ and Ar ２ are the same or different, and each independently represents １ ~C ４０ Alkyl groups of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms; ６ ~C ６０ an aryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ an alkylboron group of C ６ ~C ６０ Aryl boron group, phosphine oxide group, C １ ~C ４０ an alkylphosphine oxide group of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ and an arylphosphine oxide group of C ６ ~C ６０ and wherein the aryl amine group is selected from the group consisting of X １ ~X ３ are the same or different, and each independently represents N or C(R ６ ), where X １ ~X ３ at least two of are N; L is a single bond or C ６ ~C ６０ and heteroarylene groups having 5 to 60 ring atoms, A is a substituent represented by the following [Chemical Formula 3] or [Chemical Formula 4], 【Chemistry 3】 【Chemistry 4】 During the ceremony, Z is O, S, Se, and C(R ７ ) (R ８ ) selected from the group consisting of R １ ~R ８ are the same or different, and each independently represents a hydrogen atom, a deuterium atom (D), a halogen atom, a cyano group, a nitro group, an amino group, C １ ~C ４０ Alkyl groups of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms; ６ ~C ６０ an aryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ an alkylboron group of C ６ ~C ６０ Aryl boron group, phosphine oxide group, C １ ~C ４０ an alkylphosphine oxide group of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ and an arylphosphine oxide group of C ６ ~C ６０ or which may be joined to adjacent groups to form a fused ring; a, d, and f each independently represent an integer from 0 to 3; b, c, e, g, i, j, and k each independently represent an integer from 0 to 4; n is an integer from 1 to 3, In the above [Chemical Formula 1], the hydrogen in the benzene ring of the carbazole in which the deuterium (D) is not substituted is C １ ~C ４０ Alkyl groups of C ６ ~C ４０ and heteroaryl groups having 5 to 40 ring atoms, The arylene group and heteroarylene group of L, and the Ar １ ~Ar ２ and R １ ~R ６ The alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group, the alkylphosphine oxide group, the arylphosphine group, the arylphosphine oxide group, the arylamine group, and the fused ring each independently represent deuterium (D), a halogen, a cyano group, a nitro group, C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms; １ ~C ４０ Alkyl groups of C ６ ~C ６０ an aryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ an alkylboron group of C ６ ~C ６０ an arylboron group of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ and an arylphosphine oxide group of C ６ ~C ６０ and when there are a plurality of the above-mentioned substituents, they may be the same or different.

2. The composition for an organic electroluminescence device according to claim 1 , wherein the first host contains at least 13 deuterium (D) atoms.

3. The above Ar １ and Ar ２ are the same or different and each independently represents a substituent selected from the group consisting of the following substituents S1 to S9. 【Chemistry 5】 In the formula, * represents a bonding site with the above [Chemical Formula 1].

4. The composition for an organic electroluminescence device according to claim 1 , wherein the first host is a compound represented by the following [Chemical Formula 1A]: 【Chemistry 6】 During the ceremony, a, b, c, d, e, and f are each as defined in claim 1; m1 and m2 each represent 0 or 1.

5. 2. The composition for an organic electroluminescence device according to claim 1, wherein the first host is a compound represented by any one of the following [Chemical Formula 1a] to [Chemical Formula 1d]. 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 During the ceremony, a, b, c, d, e, f, Ar １ , and Ar ２ are each as defined in claim 1.

6. 2. The composition for an organic electroluminescence device according to claim 1, wherein the first host is a compound selected from the group consisting of the following compounds A-1 to D-4: 【Chemistry 11】 【Chemistry 12】

7. The composition for an organic electroluminescence device according to claim 1 , wherein the second host is represented by the following [Chemical Formula 5] or [Chemical Formula 6]: 【Chemistry 13】 【Chemistry 14】 During the ceremony, X １ ~X ３ , Z., L., R. １ ~R ５ , g, h, i, j, k, and n are each as defined in claim 1.

8. The composition for an organic electroluminescence device according to claim 1, wherein the second host is a compound represented by any one of the following [Chemical Formula 7] to [Chemical Formula 10]. 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 During the ceremony, X １ ~X ３ , A, L, R １ , R ３ , and i are each as defined in claim 1.

9. The above R １ The composition for an organic electroluminescence device according to claim 8 , wherein is selected from the following structural formulas: 【Chemistry 19】 In the formula, * represents a bonding site with the above [Chemical Formula 2].

10. The composition for an organic electroluminescence device according to claim 1, wherein the second host is a compound represented by any one of the following [Chemical Formula 11] to [Chemical Formula 17]. 【Chemistry 20】 【Chemistry 21】 【Chemical 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 During the ceremony, Z, L, R １ ~R ５ , g, h, i, j, k, and n are each as defined in claim 1.

11. 2. The composition for an organic electroluminescence device according to claim 1, wherein L is a single bond or a linker selected from the following structural formulas: 【Chemical 27】 In the formula, * represents a bonding site with the above [Chemical Formula 2].

12. 2. The composition for an organic electroluminescence device according to claim 1, wherein the second host is selected from the group consisting of the following compounds E-1 to E-10. 【Chemistry 28】

13. 2. The composition for an organic electroluminescence device according to claim 1, wherein the content ratio of the first host to the second host is 1:99 to 99:1 by weight.

14. The composition for an organic electroluminescence device according to claim 1 , further comprising a phosphorescent dopant.

15. The composition for an organic electroluminescence device according to claim 14 , wherein the phosphorescent dopant comprises iridium (Ir) or platinum (Pt).

16. An anode, a cathode, and one or more organic layers interposed between the anode and the cathode; An organic electroluminescence device, wherein the one or more organic layers comprise the composition according to any one of claims 1 to 15.

17. the one or more organic layers include a light-emitting layer, The organic electroluminescence device according to claim 16 , wherein the composition is contained in the light-emitting layer.

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