Composition for organic electroluminescent element and organic electroluminescent element comprising same

Abstract

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

Description

Technical Field

[0001] This invention relates to compositions for organic electroluminescent elements and organic electroluminescent elements comprising the same. Background Technology

[0002] When a voltage is applied between the two electrodes of an organic electroluminescent device (hereinafter referred to as an "organic EL device"), holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, they form excitons. When these excitons transition to the ground state, they emit light. The materials used in the organic layer can be classified according to their function as light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, and electron-injecting materials.

[0003] The light-emitting layer materials of organic EL devices can be categorized into blue, green, and red light-emitting materials based on their emission color. Additionally, yellow and orange light-emitting materials are used to produce more natural colors. Furthermore, to increase luminous efficiency through increased color purity and energy transfer, a host / dopant system can be used as the light-emitting material. Dopants can be classified into fluorescent dopants using organic materials and phosphorescent dopants using metal coordination compounds containing heavy atoms such as Ir and Pt. Since the development of such phosphorescent materials can theoretically improve luminous efficiency by up to four times compared to fluorescence, not only phosphorescent dopants but also phosphorescent host materials are attracting attention.

[0004] To date, NPB, BCP, and Alq3 are widely known as hole injection layers, hole transport layers, hole blocking layers, and electron transport layers. Regarding luminescent materials, anthracene derivatives have been reported as fluorescent dopants / host materials. In particular, phosphorescent materials, which offer significant advantages in efficiency improvement, have been used as blue, green, and red dopants by metal coordination compounds containing Ir, such as Firmic, Ir(ppy)3, and (acac)Ir(btp)2. Currently, CBP exhibits excellent properties as a phosphorescent host material.

[0005] However, while conventional organic layer materials have advantages in luminescence properties, they suffer from low glass transition temperatures and very poor thermal stability, resulting in unsatisfactory lifetime performance in organic EL devices. Therefore, there is a need to develop high-performance organic layer materials. Summary of the Invention

[0006] Technical issues

[0007] The purpose of this invention is to provide a composition that can achieve a high-efficiency and long-life organic electroluminescent element.

[0008] Another object of the present invention is to provide an organic electroluminescent element that has low driving voltage, high luminous efficiency and improved lifetime by including the above composition as an organic layer material (e.g., a light-emitting layer material).

[0009] Methods for solving problems

[0010] To achieve the above objectives, the present invention provides a composition for an organic electroluminescent element comprising a first body represented by the following chemical formula 1 and a second body represented by the following chemical formula 2:

[0011] [Chemical Formula 1]

[0012]

[0013] [Chemical Formula 2]

[0014]

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

[0016] a is an integer from 1 to 4.

[0017] b is an integer from 0 to 3.

[0018] c is an integer from 0 to 6.

[0019] d and e are each integers between 0 and 5.

[0020] R1 to R5 may be the same or different from each other, and each can be independently selected from deuterium (D) and C1 to C. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group and C6~C 40 The group composed of aryl groups.

[0021] D stands for deuterium.

[0022] Ar1 and Ar2 are each independently selected from C1 to C2. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40 aryl, heteroaryl with 5 to 40 nuclei, C1~C 40 alkoxy groups, C6~C 40 aryloxy groups, C1~C 40 alkylsilyl, C6~C 40 arylsilyl, C1~C 40 alkylboron group, C6~C 40arylboryl group, C6~C 40 arylphosphine, C6~C 40 arylphosphine oxide and C6~C 40 The group composed of aryl amino groups.

[0023] The alkyl, alkenyl, alkynyl, and aryl groups of R1 to R5 are each independently selected from deuterium (D), halogen, cyano, nitro, C1~C5. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 cycloalkyl, C6~C 40 aryl, C1~C 40 alkoxy groups, C6~C 40 aryloxy groups, C1~C 40 alkylsilyl, C6~C 40 arylsilyl, C1~C 40 alkylboron group, C6~C 40 arylboryl group, C6~C 40 arylphosphine, C6~C 40 arylphosphine oxide and C6~C 40 One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted, and when there are multiple substituents, they may be the same as or different from each other.

[0024] The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphinyl, arylphosphine oxide, and arylamine groups of Ar1 and Ar2 are each independently selected from deuterium (D), halogen, cyano, nitro, C1~C2. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40 aryl groups, heteroaryl groups with 5 to 40 nuclei, C1~C 40 alkoxy groups, C6~C 40 aryloxy groups, C1~C 40 alkylsilyl, C6~C 40 arylsilyl, C1~C 40 alkylboron group, C6~C 40 arylboryl group, C6~C 40 arylphosphine, C6~C 40 arylphosphine oxide and C6~C 40One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted, and when there are multiple substituents, they are the same as or different from each other.

[0025] In addition, the present invention provides an organic electroluminescent element comprising an anode, a cathode, and one or more organic layers between the anode and the cathode, wherein the organic layers comprise the above composition.

[0026] Invention Effects

[0027] According to one embodiment of the present invention, by using compounds with strong hole characteristics and compounds with strong electronic characteristics as the main components, it is possible to realize an organic electroluminescent element that not only has low driving voltage, high efficiency and long lifetime characteristics, but also exhibits excellent phosphorescence emission characteristics.

[0028] The effects of the present invention are not limited to the examples described above, and this specification includes a wider variety of effects. Attached Figure Description

[0029] Figure 1 This is a cross-sectional view showing the structure of an organic electroluminescent element according to an embodiment of the present invention.

[0030] <Explanation of Figure Markers>

[0031] 100: Anode; 200: Cathode;

[0032] 300: Organic layer; 310: Hole transport region;

[0033] 311: Hole injection layer; 312: Hole transport layer;

[0034] 320: Light-emitting layer; 330: Electron transport region;

[0035] 331: Electron transport layer; 332: Electron injection layer. Detailed Implementation

[0036] The advantages and features of the present invention, as well as the methods of implementing them, will become clear when referring to the embodiments described in detail with reference to the accompanying drawings. However, the invention is not limited to the embodiments disclosed below and will be implemented in various different forms. These embodiments are provided only to make the disclosure of the invention complete and to fully inform those skilled in the art of the scope of the invention, which is defined only by the claims. Therefore, in some embodiments, well-known process steps, well-known component structures, and well-known techniques are not specifically described to avoid ambiguity in the interpretation of the invention. Throughout the specification, the same reference numerals refer to the same constituent elements.

[0037] Unless otherwise defined, all terms (including technical and scientific terms) used in this specification may be used in the sense that would be commonly understood by one of ordinary skill in the art to which this invention pertains. Furthermore, unless explicitly defined otherwise, terms as defined in commonly used dictionaries should not be interpreted ideally or excessively.

[0038] Furthermore, throughout the specification, when it is stated that a certain part "contains" a certain component, unless there is a specific statement to the contrary, it means that other components may also be included, rather than excluding other components.

[0039] Furthermore, throughout the instruction manual, "above" or "on" includes not only cases where it is located above or below the object part, but also cases where there are other parts in between, and does not mean that it must be located on the upper side based on the direction of gravity.

[0040] Furthermore, in this specification, terms such as "first" and "second" do not indicate any order or degree of importance, but are used to distinguish the constituent elements from each other.

[0041] <Compositions for Organic Electroluminescent Elements>

[0042] The composition for organic electroluminescent devices of the present invention is a composition for forming an organic layer (e.g., a light-emitting layer) of an organic electroluminescent device, comprising a first substrate represented by Chemical Formula 1 and a second substrate represented by Chemical Formula 2. Here, the first substrate is an N-type substrate with relatively strong electronic characteristics, and the second substrate is a P-type substrate with relatively strong hole characteristics. By using such a first substrate and a second substrate together, the composition of the present invention can achieve a high-efficiency and long-life organic electroluminescent device.

[0043] Specifically, the first host, represented by the aforementioned chemical formula 1, has the following basic structure: the first dibenzofuran moiety, the second dibenzofuran moiety, and the diaryl-substituted triazine moiety are directly connected to each other without any connecting groups. The first dibenzofuran moiety and the second dibenzofuran moiety are bonded to each other at position 3 and position 2 of the first dibenzofuran moiety, and the diaryl-substituted triazine moiety is introduced to position 9 of the second dibenzofuran moiety. Thus, because the first dibenzofuran moiety, the second dibenzofuran moiety, and the diaryl-substituted triazine moiety are bonded to each other at specific positions, the first host can possess strong unipolar characteristics with high electronic character, improving molecular stability. Furthermore, it can generate steric hindrance, significantly improving thermal stability, and therefore can be used as an N-type host.

[0044] On the other hand, the aforementioned second host, represented by chemical formula 2, has a basic structure in which two carbazole moieties are directly bonded without a linking group. These two carbazole moieties are bonded to each other at position 3, which serves as the active site, and both carbazole moieties are substituted with deuterium (D). Thus, because the active sites within the two carbazole moieties are blocked by CC bonds and simultaneously substituted with deuterium (D), the second host can exhibit higher hole character and superior molecular stability compared to bis-carbazole compounds bonded at other positions or bis-carbazole compounds not substituted with deuterium. Therefore, it can be used as a p-type host with relatively strong hole characteristics.

[0045] The composition of the present invention, comprising the first and second bodies described above, can realize an organic electroluminescent element that not only has low driving voltage, high efficiency and long lifespan characteristics, but also exhibits excellent phosphorescent emission characteristics.

[0046] The first and second subjects will be explained in detail below.

[0047] (1) First subject

[0048] In the first entity represented by the aforementioned chemical formula 1, a is an integer from 1 to 4, b is an integer from 0 to 3, c is an integer from 0 to 6, and d and e are each an integer from 0 to 5. Wherein, when b to e are each 0, it means that hydrogen is not substituted by substituents R2, R3, R4, and R5. On the other hand, when a is an integer from 1 to 4, b is an integer from 1 to 3, c is an integer from 1 to 6, and d and e are each an integer from 1 to 5, it means that hydrogen is substituted by substituents R1, R2, R3, R4, and R5. In this case, the present invention recognizes that when at least one of more than one of R1, R2, R3, R4, and R5 is a functional group containing a heteroatom, the lone pair electrons of the heteroatom may be used as other migration paths for holes. Consequently, when excitons are formed in the luminescent layer, fewer excitons are generated than the number of holes that migrate to other migration paths, resulting in reduced efficiency. Therefore, in this invention, heteroatom-free functional groups are selectively introduced into R1, R2, R3, R4, and R5 of Formula 1. In particular, when R1, R2, R3, R4, and R5, especially R1, R4, and R5, are aryl groups, the stability to electrons can be further improved. Thus, one or more R1, R2, R3, R4, and R5 may be identical or different from each other, and each is independently selected from deuterium (D), Cl-C... 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group and C6~C 40The group composed of aryl groups.

[0049] The alkyl, alkenyl, alkynyl, and aryl groups of R1 to R5 can each be independently selected from deuterium (D), halogen, cyano, nitro, C1~C1. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 cycloalkyl, C6~C 40 aryl, C1~C 40 alkoxy groups, C6~C 40 aryloxy groups, C1~C 40 alkylsilyl, C6~C 40 arylsilyl, C1~C 40 alkylboron group, C6~C 40 arylboryl group, C6~C 40 arylphosphine, C6~C 40 arylphosphine oxide and C6~C 40 One or more substituents in the group consisting of arylamines may be substituted or unsubstituted, specifically, they may be selected from deuterium (D), halogens, cyano, nitro, C1~C1 groups. 40 Alkyl groups and C6~C 40 One or more substituents in the group consisting of aryl groups are substituted or unsubstituted. In this case, when there are multiple substituents, they may be the same as or different from each other.

[0050] As an example, R1 can be C6~C 40 The aryl group, R4 and R5 can each independently be hydrogen, deuterium (D), or C6~C. 40 The aryl group. At this point, the aryl groups of R1, R4, and R5 can each be independently selected from deuterium (D), halogen, cyano, nitro, C1~C2. 40 Alkyl groups and C6~C 40 One or more substituents in the group consisting of aryl groups may be substituted or unsubstituted, and when there are multiple substituents, they may be the same as or different from each other.

[0051] Furthermore, in the aforementioned first entity, if the first dibenzofuran portion ( Introducing an aryl group at positions 6 to 9, preferably at position 6 or 9, not only increases the glass transition temperature, but also results in a uniform morphology with high crystallinity and packing density. Therefore, the thermal stability and electron transport properties of the first host can be further improved.

[0052] Such a first subject can be a compound represented by the following chemical formula 3 or 4.

[0053] [Chemical Formula 3]

[0054]

[0055] [Chemical Formula 4]

[0056]

[0057] In the above chemical formulas 3 and 4,

[0058] R2 to R5, b, c, d, and e are each defined as described in Chemical Formula 1 above.

[0059] R 11 C6~C 40 Aryl,

[0060] f is an integer from 0 to 3.

[0061] Multiple R 12 Whether they are the same or different,

[0062] R 12 Choose free deuterium (D), C1~C 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group and C6~C 40 The group composed of aryl groups, specifically deuterium (D),

[0063] The above R 11 aryl and the above-mentioned R 12 The alkyl, alkenyl, alkynyl, and aryl groups are each independently selected from deuterium (D), halogen, cyano, nitro, C1~C2. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40 aryl groups, heteroaryl groups with 5 to 40 nuclei, C1~C 40 alkoxy groups, C6~C 40 aryloxy groups, C1~C 40 alkylsilyl, C6~C 40 arylsilyl, C1~C 40 alkylboron group, C6~C 40 arylboryl group, C6~C 40 arylphosphine, C6~C 40 arylphosphine oxide and C6~C 40 One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted, and when there are multiple substituents, they are the same as or different from each other.

[0064] As an example, in the above chemical formulas 3 and 4, R 11 The substituents can be selected from the group consisting of the following substituents S1-1 to S1-10; R4 and R5 may be the same as or different from each other, and can each independently be hydrogen or deuterium (D), or can be substituents selected from the group consisting of the following substituents S1-1 to S1-10. In this case, the following substituents S1-1 to S1-10 can each be independently substituted with deuterium (D) or not substituted.

[0065]

[0066] In the above substituents S1-1 to S1-10,

[0067] * indicates the part that connects to chemical formula 3 or 4 above.

[0068] The aforementioned first subject may be a compound represented by any of the following chemical formulas 5 to 8, depending on the type or position of the aryl group introduced into the first dibenzofuran, or whether or not deuterium is substituted, or the amount of deuterium, or the substitution position, but is not limited thereto.

[0069] [Chemical Formula 5]

[0070]

[0071] [Chemical Formula 6]

[0072]

[0073] [Chemical Formula 7]

[0074]

[0075] [Chemical Formula 8]

[0076]

[0077] In the above chemical formulas 5 to 8,

[0078] R2 to R5, b, c, d, and e are each defined as described in Chemical Formula 1 above.

[0079] Dn means being replaced by n deuterium (D) atoms, where n is one or more integers, specifically an integer from 1 to 35.

[0080] f is an integer from 0 to 3.

[0081] g is 0 or 1.

[0082] R 12 Choose free deuterium (D), C1~C 40 Alkyl groups, C2~C40 alkenyl, C2~C 40 alkynyl group and C6~C 40 The group composed of aryl groups.

[0083] The above R 12 The alkyl, alkenyl, alkynyl, and aryl groups can each be independently selected from deuterium (D), halogen, cyano, nitro, C1~C2. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40 aryl groups, heteroaryl groups with 5 to 40 nuclei, C1~C 40 alkoxy groups, C6~C 40 aryloxy groups, C1~C 40 alkylsilyl, C6~C 40 arylsilyl, C1~C 40 alkylboron group, C6~C 40 arylboryl group, C6~C 40 arylphosphine, C6~C 40 arylphosphine oxide and C6~C 40 One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted, and when there are multiple substituents, they may be the same as or different from each other.

[0084] The first subject represented by chemical formula 1 of the present invention described above can be further embodied in the following exemplary compounds, such as compounds A-1 to E-8, but is not limited thereto.

[0085]

[0086]

[0087]

[0088] (2) Second subject

[0089] The second body of the present invention improves the stability of the chemical structure by substitution with deuterium (D), and therefore, when used in conjunction with the first body, it can simultaneously achieve the characteristics of organic electroluminescent elements, such as low voltage, high efficiency and long lifespan.

[0090] As an example, the second entity contains at least 14 deuterium (D) atoms, specifically 14 to 21. The Ar1 and Ar2 atoms mentioned above may be the same as or different from each other, and can be independently selected from C6 to C6. 40The group consists of aryl groups and heteroaryl groups with 5 to 40 nuclei. In this case, the aryl and heteroaryl groups of Ar1 and Ar2 are each independently selected from deuterium (D), C1~C1. 40 Alkyl groups, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40 One or more substituents in the group consisting of aryl and heteroaryl groups with 5 to 40 nuclei are substituted or unsubstituted. When there are multiple substituents, they may be the same or different from each other. Preferably, the case in which the aryl and heteroaryl groups of Ar1 and Ar2 are both substituted with deuterium (D) is excluded.

[0091] Furthermore, in the second entity represented by the aforementioned chemical formula 2, Ar1 and Ar2 may be the same or different from each other, and each can be independently chosen from C1 to C2. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40 aryl, heteroaryl with 5 to 40 nuclei, C1~C 40 alkoxy groups, C6~C 40 aryloxy groups, C1~C 40 alkylsilyl, C6~C 40 arylsilyl, C1~C 40 alkylboron group, C6~C 40 arylboryl group, C6~C 40 arylphosphine, C6~C 40 arylphosphine oxide and C6~C 40 The group composed of arylamine groups, specifically, each group can be independently selected from C1 to C2. 40 Alkyl groups, C6~C 40 aryl groups, heteroaryl groups with 5 to 40 nuclei, and C6~C 40 It is a group composed of aryl amino groups.

[0092] The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphinyl, arylphosphine oxide, and arylamine groups of Ar1 and Ar2 are each independently selected from deuterium (D), halogen, cyano, nitro, C1~C2. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40aryl groups, heteroaryl groups with 5 to 40 nuclei, C1~C 40 alkoxy groups, C6~C 40 aryloxy groups, C1~C 40 alkylsilyl, C6~C 40 arylsilyl, C1~C 40 alkylboron group, C6~C 40 arylboryl group, C6~C 40 arylphosphine, C6~C 40 arylphosphine oxide and C6~C 40 One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted, and when there are multiple substituents, they are the same as or different from each other.

[0093] As an example, Ar1 and Ar2 may be identical or different from each other, and each can be independently selected from the group consisting of phenyl, biphenyl, naphthyl, terphenyl, tetraphenyl, and carbazole. In this case, the aforementioned phenyl, biphenyl, naphthyl, terphenyl, tetraphenyl, and carbazole groups can be selected from deuterium (D), C1~C1, and C2. 40 Alkyl groups, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40 One or more substituents in the group consisting of aryl and heteroaryl groups with 5 to 40 nuclei are substituted or unsubstituted, and when there are multiple substituents, they may be the same as or different from each other.

[0094] As another example, Ar1 can be selected from the group consisting of free phenyl, biphenyl, naphthyl, terphenyl, and tetraphenyl. Ar2 may be the same as or different from Ar1, and can be selected from the group consisting of free phenyl, biphenyl, naphthyl, terphenyl, tetraphenyl, and carbazole. In this case, the aforementioned phenyl, biphenyl, naphthyl, terphenyl, tetraphenyl, and carbazole can be selected from free deuterium (D), C1~C1, and C2. 40 Alkyl groups, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40 One or more substituents in the group consisting of aryl and heteroaryl groups with 5 to 40 nuclei are substituted or unsubstituted, and when there are multiple substituents, they may be the same as or different from each other.

[0095] As another example, Ar1 can be selected from the group consisting of free phenyl, biphenyl, naphthyl, terphenyl, and tetraphenyl. Ar2 may be the same as or different from Ar1, and can be selected from the group consisting of free phenyl, biphenyl, naphthyl, terphenyl, and tetraphenyl. In this case, the aforementioned phenyl, biphenyl, naphthyl, terphenyl, and tetraphenyl can be selected from free deuterium (D), C1~C1. 40 Alkyl groups, C3~C 40Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40 One or more substituents in the group consisting of aryl and heteroaryl groups with 5 to 40 nuclei are substituted or unsubstituted, and when there are multiple substituents, they may be the same as or different from each other.

[0096] Furthermore, the aforementioned second subject can be a compound represented by the following chemical formula 9, depending on whether Ar2 is carbazolyl or non-carbazolyl.

[0097] [Chemical Formula 9]

[0098]

[0099] In the above chemical formula 9,

[0100] Ar1 is defined the same as in chemical formula 1 above; specifically, it can be C6~C6. 40 Aryl,

[0101] h is 0 or 1.

[0102] i is an integer from 1 to 7, specifically an integer of 1 or 7.

[0103] D stands for deuterium.

[0104] Ar3 can be freely selected from C1 to C. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40 aryl, heteroaryl with 5 to 40 nuclei, C1~C 40 alkoxy groups, C6~C 40 aryloxy groups, C1~C 40 alkylsilyl, C6~C 40 arylsilyl, C1~C 40 alkylboron group, C6~C 40 arylboryl group, C6~C 40 arylphosphine, C6~C 40 arylphosphine oxide and C6~C 40 The group composed of arylamine groups, specifically, can be C6~C6. 40 Aryl,

[0105] The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphinyl, arylphosphine oxide, and arylamino groups of Ar3 can each be independently selected from deuterium (D), halogen, cyano, nitro, C1~C1.40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40 aryl groups, heteroaryl groups with 5 to 40 nuclei, C1~C 40 alkoxy groups, C6~C 40 aryloxy groups, C1~C 40 alkylsilyl, C6~C 40 arylsilyl, C1~C 40 alkylboron group, C6~C 40 arylboryl group, C6~C 40 arylphosphine, C6~C 40 arylphosphine oxide and C6~C 40 One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted, and when there are multiple substituents, they may be the same as or different from each other.

[0106] Furthermore, in the aforementioned chemical formula 9, when h is 1, the second component can be based on the third carbazole moiety ( The structure varies depending on the binding position of the three carbazole moieties. However, if the three carbazole moieties bind to each other at position 3, which is the active site, the active site is blocked by the C-C bond. Therefore, compared with tri-carbazole compounds bound at other positions, they can have higher cavitation properties and better molecular stability. Such a second host can be a compound represented by the following chemical formula 10.

[0107] [Chemical Formula 10]

[0108]

[0109] In the above chemical formula 10,

[0110] Ar1 is defined the same as in chemical formula 1 above; specifically, it can be C6~C6. 40 Aryl,

[0111] h is 0 or 1.

[0112] i is an integer from 1 to 7, specifically an integer of 1 or 7.

[0113] D stands for deuterium.

[0114] Ar3 can be freely selected from C1 to C. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40 aryl, heteroaryl with 5 to 40 nuclei, C1~C 40 alkoxy groups, C6~C 40 aryloxy groups, C1~C 40 alkylsilyl, C6~C 40 arylsilyl, C1~C 40 alkylboron group, C6~C 40 arylboryl group, C6~C 40 arylphosphine, C6~C 40 arylphosphine oxide and C6~C 40 The group composed of arylamine groups, specifically, can be C6~C6. 40 Aryl,

[0115] The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphinyl, arylphosphine oxide, and arylamino groups of Ar3 can each be independently selected from deuterium (D), halogen, cyano, nitro, C1~C1. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40 aryl groups, heteroaryl groups with 5 to 40 nuclei, C1~C 40 alkoxy groups, C6~C 40 aryloxy groups, C1~C 40 alkylsilyl, C6~C 40 arylsilyl, C1~C 40 alkylboron group, C6~C 40 arylboryl group, C6~C 40 arylphosphine, C6~C 40 arylphosphine oxide and C6~C 40 One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted, and when there are multiple substituents, they may be the same as or different from each other.

[0116] As an example, in the above chemical formula 10, Ar1 and Ar3 may be the same or different from each other, and each can be a substituent selected from the group consisting of the following substituents S2-1 to S2-10.

[0117]

[0118] In the above substituents S2-1 to S2-10, * is the site that is connected to the above chemical formula 10.

[0119] In addition, the aforementioned second subject may be a compound represented by the following chemical formula 11 or 12, depending on the Ar2, but is not limited thereto.

[0120] [Chemical Formula 11]

[0121]

[0122] [Chemical Formula 12]

[0123]

[0124] In the above chemical formulas 11 and 12,

[0125] Ar1 is defined the same as in chemical formula 1 above; specifically, it can be C6~C6. 40 The aryl group, more specifically, can be a substituent selected from the group consisting of the above-mentioned substituents S2-1 to S2-10.

[0126] j is 0 or 1.

[0127] The second subject of the present invention described above can be further embodied in the following exemplary compounds, such as compounds F-1 to F-10, but is not limited thereto.

[0128]

[0129] In this invention, "alkyl" means a monovalent substituent derived from a straight-chain or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples of substituents include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl, etc., but are not limited thereto.

[0130] In this invention, "alkenyl" means a monovalent substituent derived from a straight-chain or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon double bonds. Examples include vinyl, allyl, isopropenyl, and 2-butenyl, but are not limited thereto.

[0131] In this invention, "alkynyl" means a monovalent substituent derived from a straight-chain or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon triple bonds. Examples include ethynyl and 2-propynyl, but it is not limited to these.

[0132] In this invention, "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl groups include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, etc., but are not limited thereto.

[0133] In this invention, "heterocyclic alkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon with 3 to 40 nuclei, wherein one or more carbons in the ring, preferably 1 to 3 carbons, are replaced by heteroatoms such as N, O, S, or Se. Examples of such heterocyclic alkyl groups include morpholinoyl and piperazine, but are not limited thereto.

[0134] In this invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon with 6 to 60 carbon atoms, consisting of a single ring or a combination of two or more rings. Furthermore, it may also include forms formed by the simple attachment or condensation of two or more rings. Examples of such aryl groups include phenyl, naphthyl, phenanthryl, and anthracene, but are not limited to these.

[0135] In this invention, "heteroaryl" means a monovalent substituent derived from a mono- or poly-heterocyclic aromatic hydrocarbon with 5 to 60 atomic nuclei. In this case, one or more carbons in the ring, preferably 1 to 3 carbons, are replaced by heteroatoms such as N, O, S, or Se. Furthermore, it may include forms formed by the simple attachment or condensation of two or more rings, and further, forms formed by condensation with an aryl group. Examples of such heteroaryl groups include six-membered monocyclic groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic groups such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isooxazolyl, 2-pyridinyl, and 2-pyrimidinyl, but are not limited thereto.

[0136] In this invention, "alkoxy" is a monovalent substituent represented by R'O-, where R' means an alkyl group having 1 to 40 carbon atoms, and may include linear, branched, or cyclic structures. Examples of such alkoxy groups include methoxy, ethoxy, n-propoxy, 1-propoxy, tert-butoxy, n-butoxy, pentoxy, etc., but are not limited thereto.

[0137] In this invention, "aryloxy group" is a monovalent substituent represented by RO-, where R means an aryl group with 5 to 40 carbon atoms. Examples of such aryloxy groups include phenoxy, naphthoxy, and diphenoxy groups, but are not limited to these.

[0138] In this invention, "alkylsilyl" means a silyl group substituted with an alkyl group having 1 to 40 carbon atoms, including not only monoalkylsilyl groups but also dialkylsilyl groups and trialkylsilyl groups. Furthermore, "arylsilyl" means a silyl group substituted with an aryl group having 5 to 60 carbon atoms, including not only monoarylsilyl groups but also diarylsilyl groups, triarylsilyl groups, and other polyarylsilyl groups.

[0139] In this invention, "alkylboronyl" means a boron group substituted with an alkyl group having 1 to 40 carbon atoms, and "arylboronyl" means a boron group substituted with an aryl group having 6 to 60 carbon atoms.

[0140] In this invention, "alkylphosphine" means a phosphine group substituted with an alkyl group having 1 to 40 carbon atoms, including not only monoalkylphosphine groups but also dialkylphosphine groups. Furthermore, in this invention, "arylphosphine" means a phosphine group substituted with a monoaryl or diaryl group having 6 to 60 carbon atoms, including not only monoarylphosphine groups but also diarylphosphine groups.

[0141] In this invention, "arylamine" means an amine group that is replaced by an aryl group with 6 to 60 carbon atoms, including not only monoarylamines but also diarylamines.

[0142] In this invention, "heteroarylamine" means an amine group that is replaced by a heteroaryl group with 5 to 60 atomic nuclei, including not only mono-heteroarylamines but also di-heteroarylamines.

[0143] In this invention, (aryl)(heteroaryl)amine means an amine group substituted by an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 5 to 60 nuclei.

[0144] In this invention, "condensed ring" means a condensed aliphatic ring with 3 to 40 carbon atoms, a condensed aromatic ring with 6 to 60 carbon atoms, a condensed heteroaliphatic ring with 3 to 60 nuclei, a condensed heteroaromatic ring with 5 to 60 nuclei, a spiro ring with 3 to 60 carbon atoms, or a combination thereof.

[0145] The aforementioned first and second bodies can be contained in a weight ratio of 99:1 to 1:99, specifically in a weight ratio of 20:80 to 80:20. In this case, bipolar characteristics can be achieved more effectively while simultaneously improving efficiency and lifespan.

[0146] The compositions of the present invention may further include phosphorescent dopants. These phosphorescent dopants are substances that are mixed in trace amounts in the first and second substrates to induce luminescence. There are no particular limitations on the type of dopant, as long as it is a substance known in the art. Non-limiting examples include metal coordination compounds containing iridium (Ir) or platinum (Pt). Such dopants can induce luminescence by being excited to multiple excitations of triplet or higher states.

[0147] The aforementioned dopants can be categorized into red dopants, green dopants, and blue dopants. Red dopants, green dopants, and blue dopants commonly known in this technical field can be used without any particular restrictions.

[0148] Specifically, non-limiting examples of red dopants include PtOEP (Pt(II) octaethylporphine), Ir(piq)3(tris(2-phenylisoquinoline)iridium), Btp2Ir(acac)(bis(2-(2'-benzothienyl)-pyridinato-N,C3')iridium(acetylacetonate), or mixtures of two or more thereof.

[0149] In addition, non-limiting examples of green dopants include Ir(ppy)3(tris(2-phenylpyridine)iridium), Ir(ppy)2(acac)(Bis(2-phenylpyridine)(Acetylacetonato)iridium(III), Ir(mppy)3(tris(2-(4-tolyl)phenylpiridine)iridium), or mixtures of two or more thereof.

[0150] Other non-limiting examples of blue dopants include F2Irpic(Bis[3,5-difluoro-2-(2-pyridyl)phenyl](picolinato)iridium(III): bis[3,5-difluoro-2-(2-pyridyl)phenyl(pyridinic acid)iridium(III)), (F2ppy)2Ir(tmd), Ir(dfppz)3, or mixtures of two or more thereof.

[0151] The content of the dopant is not particularly limited. For example, based on the total amount of the composition, it can be about 0 to 30% by weight, specifically about 0.1 to 15% by weight, and more specifically about 1 to 10% by weight. In this case, based on the total amount of the composition, the total content of the first and second main components can be about 70 to 100% by weight, specifically about 85 to 99.9% by weight, and more specifically about 90 to 99% by weight.

[0152] Organic electroluminescent elements

[0153] An organic electroluminescent element according to one embodiment of the present invention includes an anode, a cathode, and one or more organic layers between the anode and the cathode, wherein the organic layers comprise the aforementioned composition. As an example, the organic layers may include a light-emitting layer, and the aforementioned composition may be included as the main component of the light-emitting layer. Therefore, the organic electroluminescent element of the present invention not only possesses low driving voltage, high efficiency, and long lifetime characteristics, but also exhibits excellent phosphorescent emission characteristics.

[0154] Hereinafter, preferred embodiments of the organic electroluminescent element of the present invention will be described with reference to the accompanying drawings. However, embodiments of the present invention can be modified in various other forms, and the scope of the present invention is not limited to the embodiments described below. To avoid repetition, descriptions of the constituent elements already described in the above-described composition for organic electroluminescent elements will be omitted.

[0155] Figure 1 This is a cross-sectional view schematically illustrating the structure of an organic electroluminescent element according to an embodiment of the present invention.

[0156] Reference Figure 1 To illustrate, an organic electroluminescent element according to an embodiment of the present invention may include an anode 100 disposed on a substrate (not shown), a cathode 200 disposed opposite to the anode, and one or more organic layers 300 disposed between the anode 100 and the cathode 200. The organic layers 300 may include a hole transport region 310, a light-emitting layer 320, and an electron transport region 330. In this case, the light-emitting layer 320 may contain the aforementioned composition as its main component. Optionally, the organic electroluminescent element of the present invention may further include a capping layer (not shown) disposed on the cathode 200.

[0157] The following is a detailed description of the various components of the organic electroluminescent element of the present invention.

[0158] (1) Anode

[0159] In the organic electroluminescent element of the present invention, the anode 100 is mainly disposed on the substrate and can be electrically connected to the driving thin film transistor to receive the driving current from the driving thin film transistor. Such an anode 100 is formed of a material with a relatively high work function, thus injecting holes into the organic layer 300, i.e., the hole transport region 310 [e.g., hole injection layer 311].

[0160] The material used to form such an anode is not particularly limited, and commonly known materials in the art can be used. For example, metals such as vanadium, chromium, copper, zinc, and gold; their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al and SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylidene-1,2-dioxothiophene] (PEDT), polypyrrole, and polyaniline; and carbon black, but are not limited thereto.

[0161] There is no particular limitation on the method for manufacturing the anode, and it can be manufactured by conventional methods known in the art. For example, the anode material can be coated onto the substrate by known thin film formation methods such as sputtering, ion plating, vacuum evaporation, and spin coating.

[0162] The aforementioned substrate is a plate-shaped component that supports organic electroluminescent elements, such as silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, but is not limited to these.

[0163] (2) Cathode

[0164] In the organic electroluminescent element of the present invention, the cathode 200 is an electrode arranged opposite to the anode, specifically disposed on the electron transport region 330. Such a cathode 200 is made of a material with a relatively low work function, thus injecting electrons into the adjacent organic layer, i.e., the electron transport region 330 [e.g., the electron injection layer 332].

[0165] The material used to form such a cathode is not particularly limited, and commonly known materials in the art can be used. For example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin, and lead; their alloys; and multilayer structures such as LiF / Al and LiO2 / Al, but are not limited to these.

[0166] The method for manufacturing the cathode is not particularly limited, and like the anode, it can be manufactured using conventional methods known in the art. For example, the cathode material can be coated onto one or more organic layers 300, specifically onto an electron transport region such as an electron injection layer 332, using the thin film forming method described above.

[0167] (3) Organic layer

[0168] In the organic electroluminescent element of the present invention, one or more organic layers 300 are disposed between the anode 100 and the cathode 200, including a hole transport region 310, a light-emitting layer 320 and an electron transport region 330.

[0169] As an example, such as Figure 1 As shown, one or more organic layers 300 may include a hole injection layer 311, a hole transport layer 312, a light-emitting layer 320, an electron transport layer 331 and an electron injection layer 332 sequentially disposed on the anode 100.

[0170] The following is a description of each organic layer.

[0171] 1) Hole transport region

[0172] In the organic electroluminescent element 100 of the present invention, the hole transport region 310 is part of the organic layer 300 disposed on the anode 100, and serves to migrate holes injected from the anode 100 to the adjacent light-emitting layer 320.

[0173] Such a hole transport region 310 may include one or more selected from the group consisting of a hole injection layer 311 and a hole transport layer 312. In this case, considering the characteristics of the organic electroluminescent element, it is preferable to include both the hole injection layer 311 and the hole transport layer 312. As an example, the hole transport region 310 is as follows... Figure 1 The diagram may include a hole injection layer 311 and a hole transport layer 312 sequentially stacked on the anode 100.

[0174] The materials constituting the hole injection layer 311 and the hole transport layer 312 of the present invention are not particularly limited as long as they have a low hole injection barrier and a high hole mobility; hole injection layer / transport layer materials used in the art can be used without limitation. In this case, the materials constituting the hole injection layer 311 and the hole transport layer 312 can be the same as or different from each other.

[0175] Specifically, the hole injection layer 311 described above contains hole injection materials known in the art. Non-limiting examples of such hole injection materials include phthalocyanine compounds such as copper phthalocyanine; and N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)phenyl]biphenyl-4,4'-diamine (N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl). -4,4'-diamine (DNTPD), 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris{N,-(2-naphthyl)-N-phenylamino}-triphenylamine (4,4',4"-tris{N,-(2-naphthyl)-N-phenylamino}-triphenylamine (tDATA) The following are examples of poly(4-styrenesulfonate): α-triphenylamine (2TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), polyaniline / camphor sulfonic acid (PANI / CSA), and polyaniline / poly(4-styrenesulfonate) (PANI / PSS). These can be used alone or in combination.

[0176] The hole transport layer 312 described above contains hole transport materials known in the art. Non-limiting examples of such hole transport materials include carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole; fluorene derivatives; amine derivatives; N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), and 4,4',4"-tris(N-carbazolyl)triphenylamine (4,4',4"-tris(N-carbazolyl)). Triphenylamine derivatives such as triphenylamine (TCTA); N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB), 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)benzenamine] (TAPC), etc., can be used alone or in combination of two or more.

[0177] The hole transport region 310 described above can be manufactured by conventional methods known in the art. For example, there are vacuum evaporation, spin coating, casting, Langmuir-Blodgett (LB) process, inkjet printing, laser printing, and laser-induced thermal imaging (LITI) methods, but it is not limited to these.

[0178] 2) Emissive layer

[0179] In the organic electroluminescent element of the present invention, the light-emitting layer 320 is a portion of the organic layer 300 between the anode 100 and the cathode 200, specifically disposed on the hole transport region 320. For example... Figure 1 As shown, the light-emitting layer 320 can be configured on the hole transport layer 312.

[0180] Such a light-emitting layer 320 is a layer of excitons formed by the combination of holes and electrons injected from the anode and cathode, respectively. Depending on the material constituting the light-emitting layer 320, the color of the light emitted by the organic electroluminescent element can be changed.

[0181] The light-emitting layer 320 of the present invention comprises the composition containing the first body represented by chemical formula 1 and the second body represented by chemical formula 2. The composition may optionally also contain a phosphorescent dopant. By including the above composition as the material of the light-emitting layer 320, the organic electroluminescent device of the present invention not only possesses low driving voltage, high efficiency, and long lifetime characteristics, but also exhibits excellent phosphorescent properties.

[0182] The light-emitting layer 320 of the present invention may be a red light-emitting layer containing a red phosphorescent material, a green light-emitting layer containing a green phosphorescent material, or a blue light-emitting layer containing a blue phosphorescent material. As an example, it may be a light-emitting layer containing a green phosphorescent material.

[0183] The aforementioned light-emitting layer 320 can be configured as: a single layer made of one material; a single layer made of multiple different materials; or a multilayer consisting of two or more layers, each made of different materials. When the light-emitting layer 320 comprises multiple layers, the organic electroluminescent element can emit light of various colors. Specifically, the present invention can provide an organic electroluminescent element that exhibits mixed colors by connecting multiple light-emitting layers made of dissimilar materials in series. Furthermore, when multiple light-emitting layers are included, the driving voltage of the element increases while the current value within the organic electroluminescent element remains constant, thus providing an organic electroluminescent element whose luminous efficiency is improved in proportion to the number of light-emitting layers.

[0184] Although not illustrated in the accompanying drawings, the organic electroluminescent element of the present invention may have multiple light-emitting stacks (not illustrated) including at least one light-emitting layer.

[0185] Such a light-emitting stack can comprise multiple light-emitting layers that emit different colors of light or emit the same color of light. That is, the color of light emitted can change depending on the material constituting the light-emitting layers. For example, multiple light-emitting stacks can contain materials that emit blue, green, red, yellow, white, etc., and can be formed using phosphorescent or fluorescent materials. In this case, the colors displayed by each light-emitting layer can be complementary. Alternatively, colors can be selected based on color combinations that emit white light. Each light-emitting layer can then contain a phosphorescent or fluorescent dopant corresponding to the selected color.

[0186] Although not illustrated in the accompanying drawings, the organic electroluminescent element of the present invention may further include a charge generation layer (CGL) (not illustrated) disposed between adjacent stacks in a plurality of light-emitting stacks and connecting them.

[0187] A charge generation layer (CGL) is a layer in an organic electroluminescent device that separates adjacent light-emitting stacks and does not directly contact the two electrodes (e.g., anode and cathode). Such a charge generation layer is disposed between two adjacent light-emitting stacks, acting as a cathode to generate electrons for one light-emitting stack and as an anode to generate holes for the other light-emitting stack. For such a charge generation layer, any material known in the art as a charge generation layer material can be used without limitation. Furthermore, it can be formed by doping conventionally known n-type and / or p-type materials with respect to the material used for the charge generation layer described above.

[0188] The aforementioned light-emitting layer 320 can be manufactured using conventional methods known in the art. Examples include vacuum evaporation, spin coating, casting, Langmuir-Blodgett (LB) process, inkjet printing, laser printing, and Laser Induced Thermal Imaging (LITI), but it is not limited to these methods. As an example, the light-emitting layer can be formed by co-deposition of the first substrate represented by chemical formula 1 and the second substrate represented by chemical formula 2. In this case, a dopant can also be co-depositioned together.

[0189] 3) Electronic transmission area

[0190] In the organic electroluminescent element of the present invention, the electron transport region 330 is an organic layer disposed on the light-emitting layer 320, which allows electrons injected from the cathode 200 to migrate to the light-emitting layer 320.

[0191] Such an electron transport region 330 may include one or more of the group consisting of electron transport layer 331 and electron injection layer 332.

[0192] As an example, electron transmission region 330, such as Figure 1 The diagram may include an electron transport layer 331 and an electron injection layer 332 sequentially stacked on the light-emitting layer 320.

[0193] In the electron transport region 330 of the present invention, for the electron transport layer 331, any electron transport material that is easy to inject electrons and has a high electron mobility can be used without limitation. Non-limiting examples of such electron transport materials include oxazole compounds, isoxazole compounds, triazole compounds, isothiazole compounds, oxadiazole compounds, thiadiazole compounds, perylene compounds, aluminum complexes [e.g., Alq3 (tris(8-quinolinolato)-aluminium)), BAlq, SAlq, Alph3, Almq3], gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc., which can be used alone or in combination of two or more.

[0194] Furthermore, the electron injection layer 332 can use electron injection materials that are easy to inject and have high electron mobility without limitation. Non-limiting examples of the aforementioned electron injection materials include lanthanide metals such as LiF, Li2O, BaO, NaCl, and CsF; or metal halides such as Yb; which can be used alone or in combination of two or more.

[0195] The electron transport region 330 of the present invention, specifically the electron transport layer 331 and / or the electron injection layer 332, can also use a material co-deposited with an n-type dopant to facilitate electron injection from the cathode 200. In this case, the n-type dopant can be any alkali metal coordination compound known in the art, such as alkali metals, alkaline earth metals, or rare earth metals.

[0196] The aforementioned electron transport region 330 can be manufactured using conventional methods known in the art. For example, methods include vacuum evaporation, spin coating, casting, Langmuir-Blodgett (LB), inkjet printing, laser printing, and laser-induced thermal imaging (LITI), but are not limited to these.

[0197] 4) Light-emitting auxiliary layer

[0198] Although not illustrated, the organic electroluminescent element of the present invention may further include a light-emitting auxiliary layer disposed between the hole transport region 310 and the light-emitting layer 320.

[0199] The luminescent auxiliary layer serves to transport holes migrating from the hole transport region 310 to the luminescent layer 320 or to block the migration of electrons and / or excitons while adjusting the thickness of the organic layer 300. In particular, the luminescent auxiliary layer has a high LUMO value to prevent electrons from migrating to the hole transport layer 312, and a high triplet energy to prevent excitons from the luminescent layer 320 from diffusing to the hole transport layer 312.

[0200] Such a light-emitting auxiliary layer can contain a hole-transporting material and can be made of the same material as the hole-transporting region. Furthermore, the light-emitting auxiliary layers of red, green, and blue organic electroluminescent elements can be made of the same material as each other.

[0201] There are no particular limitations on the materials used as luminescent auxiliary layers; for example, carbazole derivatives and arylamine derivatives are used. Specifically, examples of luminescent auxiliary layers include N,N-dinaphthyl-N,N'-diphenyl benzidine (NPD), N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-benzidine (TPD), s-TAD, and 4,4',4″-tris(N-3-methylphenyl-N-phenylamino)-triphenylamine (MTDATA), but these are not limited to these. They can be used alone or in combination.

[0202] In addition to the aforementioned substances, the light-emitting auxiliary layer may also contain a p-type dopant. As for the p-type dopant that can be used in this invention, any well-known p-type dopant commonly used in this art can be used without particular restriction. In this case, the content of the p-type dopant can be appropriately adjusted within the range known in this art; for example, based on 100 parts by weight of hole transport material, it can be approximately 0.5 to 50 parts by weight.

[0203] The aforementioned light-emitting auxiliary layer can be formed by vacuum evaporation, spin coating, casting, Langmuir-Blodgett (LB) process, inkjet printing, laser printing, laser-induced thermal imaging (LITI) and other methods as known in the art, but is not limited thereto.

[0204] 5) Cavity blocking layer

[0205] Although not illustrated, the organic electroluminescent element 100 of the present invention may further include a hole blocking layer disposed between the light-emitting layer 320 and the electron transport region 330.

[0206] The hole blocking layer 333 can prevent excitons or holes generated in the light-emitting layer 320 from diffusing (migrating) to the electron transport layer 331, thereby improving the lifetime of the organic electroluminescent device.

[0207] For the materials of such hole blocking layers, any substance with electron transport properties known in the art can be used without restriction, such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), bis(2-methyl-8-quinoline)(4-phenyl-phenol)aluminum(III) (BAlq), etc.

[0208] The aforementioned hole-blocking layer can be formed by vacuum evaporation, spin coating, casting, Langmuir-Blodgett (LB) process, inkjet printing, laser printing, laser-induced thermal imaging (LITI) and other methods known in the art, but is not limited thereto.

[0209] (4) Covering layer

[0210] Optionally, the organic electroluminescent element 100 of the present invention may further include a capping layer (not shown) disposed on the cathode 200.

[0211] The aforementioned covering layer serves to protect the organic electroluminescent element and help the light generated in the organic layer to be effectively emitted to the outside.

[0212] The aforementioned capping layer may comprise one or more materials selected from the group consisting of aluminum tri-8-hydroxyquinoline (Alq3), ZnSe, 2,5-bis(6'-(2',2″-bipyridine))-1,1-dimethyl-3,4-diphenylthiophene, 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). The material forming such a capping layer is inexpensive compared to the materials used for other layers in organic electroluminescent elements.

[0213] Such a coating can be a single layer, but it can also include two or more layers with different refractive indices so that the refractive index gradually changes as the two or more layers pass through.

[0214] The aforementioned coating can be manufactured using conventional methods known in the art, such as vacuum evaporation, spin coating, casting, or the Langmuir-Blodgett (LB) process.

[0215] The organic electroluminescent element of the present invention has a structure in which an anode 100, an organic layer 300, and a cathode 200 are sequentially stacked. Depending on the circumstances, it may also include an insulating layer (not shown) or an adhesive layer (not shown) disposed between the anode 100 and the organic layer 300 or between the cathode 200 and the organic layer 300. Such an organic electroluminescent element of the present invention maintains maximum luminous efficiency when voltage and current are applied, while the initial brightness half-life is increased, thus exhibiting excellent lifetime characteristics.

[0216] The organic electroluminescent element of the present invention can be manufactured according to conventional methods known in the art. As an example, the organic electroluminescent element can be manufactured by vacuum evaporating an anode material on a substrate, followed by sequentially vacuum evaporating a hole transport region material, a light-emitting layer material, an electron transport region material, and a cathode material on the anode.

[0217] The present invention will be described in detail below through embodiments. However, the following embodiments are merely illustrative of the present invention, and the present invention is not limited to the following embodiments.

[0218] [Preparation Example 1] Synthesis of compound DDB-1

[0219] <Step 1> 4,4,5,5-Tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborane Synthesis

[0220]

[0221] Under a nitrogen atmosphere, 7-chloro-1-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxane) (100.2 g, 394.6 mmol), Pd2(dba)3 (9.9 g, 10.8 mmol), X-Phos (23.9 g, 50.2 mmol), KOAc (67.6 g, 717.5 mmol), and 1,4-dioxane (2000 ml) were mixed and stirred at 130 °C for 12 hours.

[0222] After the reaction was completed, the organic layer was extracted with ethyl acetate, and then water was removed from the organic layer with MgSO4. The organic layer was purified by column chromatography (hexane:EA = 8:1 (v / v)) to obtain 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborane (97.0 g, yield 73%).

[0223] Mass spectrometry (theoretical value: 370.26, measured value: 370 g / mol)

[0224] <Step 2> Synthesis of 9-chloro-9'-phenyl-2,3'-bis(dibenzo[b,d]furan

[0225]

[0226] Under a nitrogen atmosphere, 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborane (97.0 g, 261.9 mmol), 8-bromo-1-chlorodibenzo[b,d]furan (88.5 g, 314.3 mmol), Pd(PPh3)4 (15.1 g, 13.1 mmol), K2CO3 (90.5 g, 654.7 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120 °C for 4 hours.

[0227] After the reaction was complete, the organic layer was extracted with dichloromethane and filtered with MgSO4. After removing the solvent from the obtained organic layer, it was purified by column chromatography (hexane:DCM = 9:1 (v / v)) to obtain 9'-chloro-9-phenyl-2,3'-bisdibenzo[b,d]furan (72.2 g, yield 62%).

[0228] Mass spectrometry (theoretical value: 444.91, measured value: 444 g / mol)

[0229] <Step 3> Synthesis of compound DDB-1

[0230]

[0231] Under a nitrogen atmosphere, 9'-chloro-9-phenyl-2,3'-bis(dibenzo[b,d]furan) (72.2 g, 162.4 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborane) (45.4 g, 178.6 mmol), Pd2(dba)3 (4.5 g, 4.9 mmol), X-Phos (10.8 g, 22.7 mmol), KOAc (30.6 g, 324.7 mmol), and 1,4-dioxane (2000 ml) were mixed and stirred at 130 °C for 12 hours.

[0232] After the reaction was completed, the organic layer was extracted with ethyl acetate, and then water was removed from the organic layer with MgSO4. The organic layer was purified by column chromatography (hexane:EA = 8:1 (v / v)) to obtain DDB-1 (54.9 g, yield 63%).

[0233] Mass spectrometry (theoretical value: 536.43, measured value: 536 g / mol)

[0234] [Preparation Example 2] Synthesis of compound DDB-2

[0235] <Step 1>

[0236]

[0237] The target compound was obtained by replacing 7-chloro-1-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) in step 1 of Preparation Example 1 with 3-chloro-6-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol). Otherwise, the same procedure as step 1 of Preparation Example 1 was performed to obtain the target compound.

[0238] <Step 2>

[0239]

[0240] The target compound was obtained by replacing the 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborane used in step 2 of preparation example 1 with the target compound obtained in step 1 of preparation example 1. Otherwise, the same process as step 2 of preparation example 1 was performed to obtain the target compound.

[0241] <Step 3> - Synthesis of compound DDB-2

[0242]

[0243] The target compound obtained in step 2 of Preparation Example 2 was used instead of 9'-chloro-9-phenyl-2,3'-bis(dibenzo[b,d]furan) used in step 3 of Preparation Example 1. Otherwise, the same process as step 3 of Preparation Example 1 was performed to obtain the target compound DDB-2 (71.8 g, final yield 37.3%).

[0244] Mass spectrometry (theoretical value: 536.43, measured value: 536 g / mol)

[0245] [Preparation Example 3] Synthesis of Compound DDB-3

[0246] <Step 1>

[0247]

[0248] The target compound was obtained by replacing 1-([1,1'-biphenyl]-4-yl)-7-chlorodibenzo[b,d]furan (100.0 g, 282.4 mmol) in step 1 of Preparation Example 1 with 1-([1,1'-biphenyl]-4-yl)-7-chlorodibenzo[b,d]furan (100.0 g, 358.7 mmol), except that the same procedure as step 1 of Preparation Example 1 was performed.

[0249] <Step 2>

[0250]

[0251] The target compound was obtained by replacing the 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborane used in step 2 of preparation example 1 with the target compound obtained in step 1 of preparation example 3. Otherwise, the same process as step 2 of preparation example 1 was performed to obtain the target compound.

[0252] <Step 3> - Synthesis of compound DDB-3

[0253]

[0254] The target compound obtained in step 2 of Preparation Example 3 was used instead of 9'-chloro-9-phenyl-2,3'-bisdibenzo[b,d]furan in step 3 of Preparation Example 1. Otherwise, the same process as in step 3 of Preparation Example 1 was performed to obtain the target compound DDB-3 (48.2 g, final yield 27.8%).

[0255] Mass spectrometry (theoretical value: 612.53, measured value: 612 g / mol)

[0256] [Preparation Example 4] Synthesis of Compound DDB-4

[0257] <Step 1>

[0258]

[0259] The target compound was obtained by replacing 7-chloro-1-phenyldibenzo[b,d]furan-2,3,4,6,8,9-d6 (100.0 g, 345.1 mmol) used in step 1 of Preparation Example 1 with 7-chloro-1-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol). Otherwise, the same procedure as step 1 of Preparation Example 1 was performed to obtain the target compound.

[0260] <Step 2>

[0261]

[0262] The target compound was obtained in step 1 of Preparation Example 4 above, instead of 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborane used in step 2 of Preparation Example 1. 8-bromo-1-chlorodibenzo[b,d]furan-2,3,4,6,7,9-d6 (75.0 g, 260.9 mmol) was used instead of 8-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol). Otherwise, the same procedure as step 2 of Preparation Example 1 was performed to obtain the target compound.

[0263] <Step 3> - Synthesis of compound DDB-4

[0264]

[0265] The target compound obtained in step 2 of Preparation Example 4 was used instead of 9'-chloro-9-phenyl-2,3'-bisdibenzo[b,d]furan in step 3 of Preparation Example 1. Otherwise, the same process as in step 3 of Preparation Example 1 was performed to obtain the target compound DDB-4 (37.5 g, final yield 19.7%).

[0266] Mass spectrometry (theoretical value: 553.54, measured value: 553 g / mol)

[0267] [Preparation Example 5] Synthesis of Compound DDB-5

[0268] <Step 1>

[0269]

[0270] The target compound was obtained by replacing 7-chloro-1-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) in step 1 of Preparation Example 1 with 3-chloro-6-(phenyl-d5)dibenzo[b,d]furan-1,2,4,7,8,9-d6 (100.0 g, 345.1 mmol).

[0271] <Step 2>

[0272]

[0273] The target compound was obtained in step 1 of Preparation Example 5 in place of 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborane used in step 2 of Preparation Example 1, and 8-bromo-1-chlorodibenzo[b,d]furan-2,3,4,6,7,9-d6 (71.4 g, 248.4 mmol) was used in place of 8-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol). Otherwise, the same procedure as step 2 of Preparation Example 1 was performed to obtain the target compound.

[0274] <Step 3> - Synthesis of compound DDB-5

[0275]

[0276] The target compound obtained in step 2 of Preparation Example 5 was used instead of 9'-chloro-9-phenyl-2,3'-bisdibenzo[b,d]furan in step 3 of Preparation Example 1. Otherwise, the same process as step 3 of Preparation Example 1 was performed to obtain the target compound DDB-5 (41.2 g, final yield 21.6%).

[0277] Mass spectrometry (theoretical value: 553.54, measured value: 553 g / mol)

[0278] [Synthetic Example 1] Synthesis of Compound A-1

[0279]

[0280] Under a nitrogen gas flow, compound DDB-1 (10.0 g, 18.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.0 g, 22.4 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), K2CO3 (6.4 g, 46.6 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) obtained in Preparation Example 1 were mixed and stirred at 120 °C for 4 hours.

[0281] After the reaction was complete, the organic layer was extracted with dichloromethane and filtered with MgSO4. After removing the solvent from the obtained organic layer, it was purified by column chromatography (hexane:EA = 4:1 (v / v)) to obtain the target compound A-1 (7.8 g, yield 65%).

[0282] Mass spectrometry (theoretical value: 641.73, measured value: 641 g / mol)

[0283] [Synthetic Example 2] Synthesis of Compound A-2

[0284]

[0285] Using 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.2 g, 22.4 mmol) instead of the 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1, the same procedure as in Synthesis Example 1 was performed to obtain target compound A-2 (7.4 g, yield 61%).

[0286] Mass spectrometry (theoretical value: 651.79, measured value: 651 g / mol)

[0287] [Synthetic Example 3] Synthesis of Compound A-3

[0288]

[0289] Using 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1, the same procedure as in Synthesis Example 1 was performed to obtain target compound A-3 (8.6 g, yield 64%).

[0290] Mass spectrometry (theoretical value: 717.83, measured value: 717 g / mol)

[0291] [Synthetic Example 4] Synthesis of Compound A-4

[0292]

[0293] Using 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1, the same procedure as in Synthesis Example 1 was performed to obtain target compound A-4 (9.1 g, yield 68%).

[0294] Mass spectrometry (theoretical value: 717.83, measured value: 717 g / mol)

[0295] [Synthetic Example 5] Synthesis of Compound A-5

[0296]

[0297] Using 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1, the same procedure as in Synthesis Example 1 was performed to obtain the target compound A-5 (8.3 g, yield 62%).

[0298] Mass spectrometry (theoretical value: 717.83, measured value: 717 g / mol)

[0299] [Synthetic Example 6] Synthesis of Compound A-6

[0300]

[0301] Using 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1, the same procedure as in Synthesis Example 1 was performed to obtain the target compound A-6 (9.9 g, yield 67%).

[0302] Mass spectrometry (theoretical value: 793.93, measured value: 793 g / mol)

[0303] [Synthetic Example 7] Synthesis of Compound A-7

[0304]

[0305] Using 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1, the same procedure as in Synthesis Example 1 was performed to obtain the target compound A-7 (8.9 g, yield 60%).

[0306] Mass spectrometry (theoretical value: 793.93, measured value: 793 g / mol)

[0307] [Synthetic Example 8] Synthesis of Compound A-8

[0308]

[0309] Using 2,4-bis([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1, the same procedure as in Synthesis Example 1 was performed to obtain the target compound A-8 (9.6 g, yield 65%).

[0310] Mass spectrometry (theoretical value: 793.93, measured value: 793 g / mol)

[0311] [Synthetic Example 9] Synthesis of Compound B-1

[0312]

[0313] Under a nitrogen gas flow, compound DDB-2 (10.0 g, 18.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.0 g, 22.4 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), K2CO3 (6.4 g, 46.6 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) obtained in Preparation Example 2 were mixed and stirred at 120 °C for 4 hours.

[0314] After the reaction was complete, the organic layer was extracted with dichloromethane and filtered with MgSO4. After removing the solvent from the obtained organic layer, it was purified by column chromatography (hexane:EA = 4:1 (v / v)) to obtain the target compound B-1 (7.8 g, yield 65%).

[0315] Mass spectrometry (theoretical value: 641.73, measured value: 641 g / mol)

[0316] [Synthetic Example 10] Synthesis of Compound B-2

[0317]

[0318] Using 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.2 g, 22.4 mmol) instead of the 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 9, the same procedure as in Synthesis Example 9 was performed to obtain the target compound B-2 (7.8 g, yield 64%).

[0319] Mass spectrometry (theoretical value: 651.79, measured value: 651 g / mol)

[0320] [Synthetic Example 11] Synthesis of Compound B-3

[0321]

[0322] Using 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 9, the same procedure as in Synthesis Example 9 was performed to obtain the target compound B-3 (8.8 g, yield 66%).

[0323] Mass spectrometry (theoretical value: 717.83, measured value: 717 g / mol)

[0324] [Synthetic Example 12] Synthesis of Compound B-4

[0325]

[0326] Using 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 9, the same procedure as in Synthesis Example 9 was performed to obtain the target compound B-4 (8.4 g, yield 63%).

[0327] Mass spectrometry (theoretical value: 717.83, measured value: 717 g / mol)

[0328] [Synthetic Example 13] Synthesis of Compound B-5

[0329]

[0330] Using 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 9, the same procedure as in Synthesis Example 9 was performed to obtain the target compound B-5 (8.6 g, yield 64%).

[0331] Mass spectrometry (theoretical value: 717.83, measured value: 717 g / mol)

[0332] [Synthetic Example 14] Synthesis of Compound B-6

[0333]

[0334] Using 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 9, the same procedure as in Synthesis Example 9 was performed to obtain the target compound B-6 (9.9 g, yield 67%).

[0335] Mass spectrometry (theoretical value: 793.93, measured value: 793 g / mol)

[0336] [Synthetic Example 15] Synthesis of Compound B-7

[0337]

[0338] Using 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 9, the same procedure as in Synthesis Example 9 was performed to obtain the target compound B-7 (9.2 g, yield 62%).

[0339] Mass spectrometry (theoretical value: 793.93, measured value: 793 g / mol)

[0340] [Synthetic Example 16] Synthesis of Compound B-8

[0341]

[0342] Using 2,4-bis([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 9, the same procedure as in Synthesis Example 9 was performed to obtain the target compound B-8 (9.5 g, yield 64%).

[0343] Mass spectrometry (theoretical value: 793.93, measured value: 793 g / mol)

[0344] [Synthetic Example 17] Synthesis of Compound C-1

[0345]

[0346] Under a nitrogen gas flow, compound DDB-3 (10.0 g, 16.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.2 g, 19.6 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.6 g, 40.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) obtained in Preparation Example 3 were mixed and stirred at 120 °C for 4 hours.

[0347] After the reaction was complete, the organic layer was extracted with dichloromethane and filtered with MgSO4. After removing the solvent from the obtained organic layer, it was purified by column chromatography (hexane:EA = 4:1 (v / v)) to obtain the target compound C-1 (7.6 g, yield 65%).

[0348] Mass spectrometry (theoretical value: 717.83, measured value: 717 g / mol)

[0349] [Synthetic Example 18] Synthesis of Compound C-2

[0350]

[0351] The target compound C-2 (7.8 g, 64% yield) was obtained by replacing 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.4 g, 19.6 mmol) used in Synthesis Example 17 with 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.4 g, 19.6 mmol).

[0352] Mass spectrometry (theoretical value: 727.89, measured value: 727 g / mol)

[0353] [Synthetic Example 19] Synthesis of Compound C-3

[0354]

[0355] Using 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 17, the same procedure as in Synthesis Example 17 was performed to obtain the target compound C-3 (8.0 g, yield 62%).

[0356] Mass spectrometry (theoretical value: 793.93, measured value: 793 g / mol)

[0357] [Synthetic Example 20] Synthesis of Compound C-4

[0358]

[0359] Using 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 17, the same procedure as in Synthesis Example 17 was performed to obtain the target compound C-4 (8.7 g, yield 67%).

[0360] Mass spectrometry (theoretical value: 793.93, measured value: 793 g / mol)

[0361] [Synthetic Example 21] Synthesis of Compound C-5

[0362]

[0363] Using 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 17, the same procedure as in Synthesis Example 17 was performed to obtain the target compound C-5 (7.9 g, yield 61%).

[0364] Mass spectrometry (theoretical value: 793.93, measured value: 793 g / mol)

[0365] [Synthetic Example 22] Synthesis of Compound C-6

[0366]

[0367] Using 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (8.2 g, 19.6 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 17, the same procedure as in Synthesis Example 17 was performed to obtain the target compound C-6 (8.9 g, yield 63%).

[0368] Mass spectrometry (theoretical value: 870.02, measured value: 870 g / mol)

[0369] [Synthetic Example 23] Synthesis of Compound C-7

[0370]

[0371] Using 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (8.2 g, 19.6 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 17, the same procedure as in Synthesis Example 17 was performed to obtain the target compound C-7 (9.4 g, yield 66%).

[0372] Mass spectrometry (theoretical value: 870.02, measured value: 870 g / mol)

[0373] [Synthetic Example 24] Synthesis of Compound C-8

[0374]

[0375] Using 2,4-bis([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (8.2 g, 19.6 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 17, the same procedure as in Synthesis Example 17 was performed to obtain the target compound C-8 (8.7 g, yield 61%).

[0376] Mass spectrometry (theoretical value: 870.02, measured value: 870 g / mol)

[0377] [Synthetic Example 25] Synthesis of Compound D-1

[0378]

[0379] Under a nitrogen gas flow, compound DDB-4 (10.0 g, 18.1 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.8 g, 21.7 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), K2CO3 (6.2 g, 45.2 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) obtained in Preparation Example 4 were mixed and stirred at 120 °C for 4 hours.

[0380] After the reaction was complete, the organic layer was extracted with dichloromethane and filtered with MgSO4. After removing the solvent from the obtained organic layer, it was purified by column chromatography (hexane:EA = 4:1 (v / v)) to obtain the target compound D-1 (8.1 g, yield 68%).

[0381] Mass spectrometry (theoretical value: 658.83, measured value: 658 g / mol)

[0382] [Synthetic Example 26] Synthesis of Compound D-2

[0383]

[0384] Using 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.0 g, 21.7 mmol) instead of the 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 25, the same procedure as in Synthesis Example 25 was performed to obtain the target compound D-2 (8.1 g, yield 67%).

[0385] Mass spectrometry (theoretical value: 668.89, measured value: 668 g / mol)

[0386] [Synthetic Example 27] Synthesis of Compound D-3

[0387]

[0388] Using 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 25, the same procedure as in Synthesis Example 25 was performed to obtain the target compound D-3 (8.6 g, yield 65%).

[0389] Mass spectrometry (theoretical value: 734.93, measured value: 734 g / mol)

[0390] [Synthetic Example 28] Synthesis of Compound D-4

[0391]

[0392] Using 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 25, the same procedure as in Synthesis Example 25 was performed to obtain the target compound D-4 (9.3 g, yield 70%).

[0393] Mass spectrometry (theoretical value: 734.93, measured value: 734 g / mol)

[0394] [Synthetic Example 29] Synthesis of Compound D-5

[0395]

[0396] Using 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 25, the same procedure as in Synthesis Example 25 was performed to obtain the target compound D-5 (8.9 g, yield 67%).

[0397] Mass spectrometry (theoretical value: 734.93, measured value: 734 g / mol)

[0398] [Synthetic Example 30] Synthesis of Compound D-6

[0399]

[0400] Using 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.1 g, 21.7 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 25, the same procedure as in Synthesis Example 25 was performed to obtain the target compound D-6 (9.5 g, yield 65%).

[0401] Mass spectrometry (theoretical value: 811.03, measured value: 811 g / mol)

[0402] [Synthetic Example 31] Synthesis of Compound D-7

[0403]

[0404] Using 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (9.1 g, 21.7 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 25, the same procedure as in Synthesis Example 25 was performed to obtain the target compound D-7 (10.4 g, yield 71%).

[0405] Mass spectrometry (theoretical value: 811.03, measured value: 811 g / mol)

[0406] [Synthetic Example 32] Synthesis of Compound D-8

[0407]

[0408] Using 2,4-bis([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.1 g, 21.7 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 25, the same procedure as in Synthesis Example 25 was performed to obtain the target compound D-8 (10.7 g, yield 73%).

[0409] Mass spectrometry (theoretical value: 811.03, measured value: 811 g / mol)

[0410] [Synthetic Example 33] Synthesis of Compound E-1

[0411]

[0412] Under a nitrogen gas flow, compound DDB-5 (10.0 g, 18.1 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.8 g, 21.7 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), K2CO3 (6.2 g, 45.2 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120 °C for 4 hours.

[0413] After the reaction was complete, the organic layer was extracted with dichloromethane and filtered with MgSO4. After removing the solvent from the obtained organic layer, it was purified by column chromatography (hexane:EA = 4:1 (v / v)) to obtain the target compound E-1 (7.6 g, yield 64%).

[0414] Mass spectrometry (theoretical value: 658.83, measured value: 658 g / mol)

[0415] [Synthetic Example 34] Synthesis of Compound E-2

[0416]

[0417] Using 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.0 g, 21.7 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 33, the same procedure as in Synthesis Example 33 was performed to obtain the target compound E-2 (8.0 g, yield 66%).

[0418] Mass spectrometry (theoretical value: 668.89, measured value: 668 g / mol)

[0419] [Synthetic Example 35] Synthesis of Compound E-3

[0420]

[0421] Using 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 33, the same procedure as in Synthesis Example 33 was performed to obtain the target compound E-3 (8.8 g, yield 66%).

[0422] Mass spectrometry (theoretical value: 734.93, measured value: 734 g / mol)

[0423] [Synthetic Example 36] Synthesis of Compound E-4

[0424]

[0425] Using 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 33, the same procedure as in Synthesis Example 33 was performed to obtain the target compound E-4 (8.6 g, yield 65%).

[0426] Mass spectrometry (theoretical value: 734.93, measured value: 734 g / mol)

[0427] [Synthetic Example 37] Synthesis of Compound E-5

[0428]

[0429] Using 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 33, the same procedure as in Synthesis Example 33 was performed to obtain the target compound E-5 (9.3 g, yield 70%).

[0430] Mass spectrometry (theoretical value: 734.93, measured value: 734 g / mol)

[0431] [Synthetic Example 38] Synthesis of Compound E-6

[0432]

[0433] Using 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.1 g, 21.7 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 33, the same procedure as in Synthesis Example 33 was performed to obtain the target compound E-6 (10.7 g, yield 73%).

[0434] Mass spectrometry (theoretical value: 811.03, measured value: 811 g / mol)

[0435] [Synthetic Example 39] Synthesis of Compound E-7

[0436]

[0437] Using 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (9.1 g, 21.7 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 33, the same procedure as in Synthesis Example 33 was performed to obtain the target compound E-7 (10.0 g, yield 68%).

[0438] Mass spectrometry (theoretical value: 811.03, measured value: 811 g / mol)

[0439] [Synthetic Example 40] Synthesis of Compound E-8

[0440]

[0441] Using 2,4-bis([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.1 g, 21.7 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 33, the same procedure as in Synthesis Example 33 was performed to obtain the target compound E-8 (10.4 g, yield 71%).

[0442] Mass spectrometry (theoretical value: 811.03, measured value: 811 g / mol)

[0443] [Preparation Example 6] Synthesis of compound Cz-D1

[0444]

[0445] Under a nitrogen atmosphere, 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.

[0446] After the reaction was completed, the organic layer was extracted with ethyl acetate, and then the water was removed with MgSO4. The solution was purified by column chromatography (hexane:EA = 5:1 (v / v)) to obtain Cz-D1 (125.7 g, yield 72%).

[0447] Mass spectrometry (theoretical value: 329.25, measured value: 329 g / mol)

[0448] [Preparation Example 7] Synthesis of compound Cz-D2

[0449]

[0450] Using 4-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) instead of the iodobenzene used in Preparation Example 6, the same procedure as in Preparation Example 6 was performed to obtain the target compound Cz-D2 (135.5 g, yield 63%).

[0451] Mass spectrometry (theoretical value: 405.35, measured value: 405 g / mol)

[0452] [Preparation Example 8] Synthesis of compound Cz-D3

[0453]

[0454] 3-Iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene used in Preparation Example 6. Otherwise, the same procedure as in Preparation Example 6 was performed to obtain the target compound Cz-D3 (148.4 g, yield 69%).

[0455] Mass spectrometry (theoretical value: 405.35, measured value: 405 g / mol)

[0456] [Preparation Example 9] Synthesis of compound Cz-D4

[0457]

[0458] 2-Iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene used in Preparation Example 6. Otherwise, the same procedure as in Preparation Example 6 was performed to obtain the target compound Cz-D4 (96.8 g, yield 45%).

[0459] Mass spectrometry (theoretical value: 405.35, measured value: 405 g / mol)

[0460] [Preparation Example 10] Synthesis of compound BCz-D1

[0461] <Step 1> 9-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)-9H-carbazole-1,2,4, Synthesis of 5,6,7,8-d7

[0462]

[0463] Under a nitrogen stream, compound Cz-D1 (100.0 g, 303.7 mmol) obtained in Preparation Example 6, 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborane) (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.

[0464] After the reaction was completed, the organic layer was extracted with ethyl acetate, and then the water was removed with MgSO4. The solution was purified by column chromatography (hexane:EA = 8:1 (v / v)) to obtain the target compound 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7 (96.0 g, yield 84%).

[0465] Mass spectrometry (theoretical value: 376.3, measured value: 376 g / mol)

[0466] <Step 2> Synthesis of compound BCz-D1

[0467]

[0468] Under a nitrogen stream, 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-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.

[0469] After the reaction was complete, the organic layer was extracted with dichloromethane and filtered with MgSO4. After removing the solvent from the obtained organic layer, it was purified by column chromatography (hexane:EA = 7:1 (v / v)) to obtain the target compound BCz-D1 (71.1 g, yield 66%).

[0470] Mass spectrometry (theoretical value: 422.59, measured value: 422 g / mol)

[0471] [Preparation Example 11] Synthesis of compound BCz-D2

[0472] <Step 1>

[0473]

[0474] The compound Cz-D2 (100g, 246.7mmol) obtained in Preparation Example 7 was used instead of the compound Cz-D1 used in step 1 of Preparation Example 10. Otherwise, the same process as step 1 of Preparation Example 10 was performed to obtain the target compound.

[0475] <Step 2>

[0476]

[0477] The target compound obtained in step 1 of Preparation Example 11 was used instead of 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7 in step 2 of Preparation Example 10. Otherwise, the same process as in step 2 of Preparation Example 10 was performed to obtain the target compound BCz-D2 (66.4 g, final yield 54.0%).

[0478] Mass spectrometry (theoretical value: 498.69, measured value: 498 g / mol)

[0479] [Preparation Example 12] Synthesis of compound BCz-D3

[0480] <Step 1>

[0481]

[0482] The compound Cz-D3 (100g, 246.7mmol) obtained in Preparation Example 8 was used instead of the compound Cz-D1 used in step 1 of Preparation Example 10. Otherwise, the same procedure as step 1 of Preparation Example 10 was followed to obtain the target compound.

[0483] <Step 2>

[0484]

[0485] The target compound obtained in step 1 of Preparation Example 12 was used instead of 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7 in step 2 of Preparation Example 10. Otherwise, the same process as in step 2 of Preparation Example 10 was performed to obtain the target compound BCz-D3 (59.7 g, final yield 48.5%).

[0486] Mass spectrometry (theoretical value: 498.69, measured value: 498 g / mol)

[0487] [Preparation Example 13] Synthesis of compound BCz-D4

[0488] <Step 1>

[0489]

[0490] The compound Cz-D4 (100g, 246.7mmol) obtained in Preparation Example 9 was used instead of Cz-D1 in step 1 of Preparation Example 10. Otherwise, the same process as step 1 of Preparation Example 10 was performed to obtain the target compound.

[0491] <Step 2>

[0492]

[0493] The target compound obtained in step 1 of Preparation Example 13 was used instead of 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7 in step 2 of Preparation Example 10. Otherwise, the same process as in step 2 of Preparation Example 10 was performed to obtain the target compound BCz-D4 (59.4 g, final yield 48.3%).

[0494] Mass spectrometry (theoretical value: 498.69, measured value: 498 g / mol)

[0495] [Synthetic Example 41] Synthesis of Compound F-1

[0496]

[0497] Under a nitrogen atmosphere, compound BCz-D1 (10.0 g, 23.6 mmol) obtained in Preparation Example 10, compound Cz-D1 (9.3 g, 28.3 mmol) obtained in Preparation Example 6, 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 complete, the toluene was concentrated and the solid salt was filtered off. The mixture was then purified by recrystallization to obtain the target compound F-1 (13.0 g, yield 82%).

[0498] Mass spectrometry (theoretical value: 670.93, measured value: 670 g / mol)

[0499] [Synthetic Example 42] Synthesis of Compound F-2

[0500]

[0501] The compound Cz-D2 (11.4 g, 28.3 mmol) obtained in Preparation Example 7 was used instead of the compound Cz-D1 used in Synthesis Example 41. Otherwise, the same procedure as in Synthesis Example 41 was performed to obtain the target compound F-2 (13.8 g, yield 78%).

[0502] Mass spectrometry (theoretical value: 747.02, measured value: 747 g / mol)

[0503] [Synthetic Example 43] Synthesis of Compound F-3

[0504]

[0505] The compound Cz-D3 (11.4 g, 28.3 mmol) obtained in Preparation Example 8 was used instead of the compound Cz-D1 used in Synthesis Example 41. Otherwise, the same procedure as in Synthesis Example 41 was performed to obtain the target compound F-3 (13.2 g, yield 75%).

[0506] Mass spectrometry (theoretical value: 747.02, measured value: 747 g / mol)

[0507] [Synthetic Example 44] Synthesis of Compound F-4

[0508]

[0509] The compound Cz-D4 (11.4 g, 28.3 mmol) obtained in Preparation Example 9 was used instead of the compound Cz-D1 used in Synthesis Example 41. Otherwise, the same process as in Synthesis Example 41 was performed to obtain the target compound F-4 (12.2 g, yield 69%).

[0510] Mass spectrometry (theoretical value: 747.02, measured value: 747 g / mol)

[0511] [Synthetic Example 45] Synthesis of Compound F-5

[0512]

[0513] Under a nitrogen atmosphere, compound BCz-D2 (10.0 g, 20.1 mmol) obtained in Preparation Example 11, compound Cz-D1 (7.9 g, 24.1 mmol) obtained in Preparation Example 6, 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 complete, the toluene was concentrated and the solid salt was filtered. The mixture was then purified by recrystallization to obtain the target compound F-5 (10.2 g, yield 62%).

[0514] Mass spectrometry (theoretical value: 747.02, measured value: 747 g / mol)

[0515] [Synthetic Example 46] Synthesis of Compound F-6

[0516]

[0517] Under a nitrogen atmosphere, compound BCz-D3 (10.0 g, 20.1 mmol) obtained in Preparation Example 12, compound Cz-D1 (7.9 g, 24.1 mmol) obtained in Preparation Example 6, 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 complete, the toluene was concentrated and the solid salt was filtered off. The mixture was then purified by recrystallization to obtain the target compound F-6 (9.4 g, yield 63%).

[0518] Mass spectrometry (theoretical value: 747.02, measured value: 747 g / mol)

[0519] [Synthetic Example 47] Synthesis of Compound F-7

[0520]

[0521] Under a nitrogen atmosphere, compound BCz-D4 (10.0 g, 20.1 mmol) obtained in Preparation Example 13, compound Cz-D1 (7.9 g, 24.1 mmol) obtained in Preparation Example 6, 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 complete, the toluene was concentrated and the solid salt was filtered off. The mixture was then purified by recrystallization to obtain the target compound F-7 (8.1 g, yield 54%).

[0522] Mass spectrometry (theoretical value: 747.02, measured value: 747 g / mol)

[0523] [Synthetic Example 48] Synthesis of Compound F-8

[0524]

[0525] The compound Cz-D1 used in Synthesis Example 41 was replaced with 4-bromo-1,1'-biphenyl (6.6 g, 28.3 mmol), otherwise the same procedure as in Synthesis Example 41 was performed to obtain the target compound F-8 (9.9 g, 73% yield).

[0526] Mass spectrometry (theoretical value: 574.79, measured value: 574 g / mol)

[0527] [Synthetic Example 49] Synthesis of Compound F-9

[0528]

[0529] The compound Cz-D1 used in Synthesis Example 45 was replaced with 4-bromo-1,1'-biphenyl (5.6 g, 24.1 mmol), and the same procedure as in Synthesis Example 45 was performed to obtain the target compound F-9 (10.2 g, yield 78%).

[0530] Mass spectrometry (theoretical value: 650.88, measured value: 650 g / mol)

[0531] [Synthetic Example 50] Synthesis of Compound F-10

[0532]

[0533] The compound Cz-D1 used in Synthesis Example 46 was replaced with 4-bromo-1,1'-biphenyl (5.6 g, 24.1 mmol), and the same procedure as in Synthesis Example 46 was performed to obtain the target compound F-10 (9.8 g, 75% yield).

[0534] Mass spectrometry (theoretical value: 650.88, measured value: 650 g / mol)

[0535] [Example 1] Fabrication of Green Organic EL Components

[0536] After refining the compound A-1 synthesized in Synthesis Example 1 and the compound E-1 synthesized in Synthesis Example 41 to high purity using commonly known methods, a green organic EL element was fabricated according to the following process.

[0537] First, a glass substrate coated with an indium tin oxide (ITO) film at a thickness of 1500 Å was ultrasonically washed with distilled water. After washing with distilled water, it was ultrasonically washed with solvents such as isopropanol, acetone, and methanol, and then dried. It was then transferred to a UV ozone cleaner (Power sonic 405, Hwashintech), where it was cleaned with UV light for 5 minutes. Finally, the substrate was transferred to a vacuum evaporation machine.

[0538] Organic EL elements were fabricated on the prepared ITO transparent electrode by stacking the following layers in the order of HT + 2% PA (100Å) / HT (1200Å) / HA (300Å) / 30% compound F-1 + 60% compound A-1 + 10% Ir(ppy)3 (400Å) / EA (50Å) / ET + LiQ (300Å_1:1) / LiF (10Å) / Al (1000Å). The structures of HT, HA, PA, Ir(ppy)3, EA, and ET used are as follows.

[0539]

[0540] [Example 2] ~ [Example 400] - Manufacturing of Green Organic EL Components

[0541] In Example 1, when forming the light-emitting layer, compounds F-2 to F-10 synthesized in each of Synthesis Examples 42 to 50 were used instead of compound F-1 as the main light-emitting material, and compounds A-2 to E-8 synthesized in each of Synthesis Examples 2 to 40 were used instead of compound A-1 (see Table 1). Otherwise, the green organic EL element was manufactured in the same manner as in Example 1.

[0542] [Comparative Example 1] Fabrication of Green Organic EL Components

[0543] In Example 1, when forming the light-emitting layer, compound HT-1 was used instead of compound F-1 as the main light-emitting material, and compound ET-1 was used instead of compound A-1. Otherwise, the green organic EL element was fabricated using the same process as in Example 1. The structures of HT-1 and ET-1 used at this time are as follows.

[0544]

[0545] [Evaluation Example 1]

[0546] For the green organic EL elements manufactured in Examples 1 to 400 and Comparative Example 1, respectively, a current density of 10 mA / cm² was measured. 2 The driving voltage, current efficiency, emission peak, and lifetime were determined, and the results are shown in Table 1 below.

[0547] [Table 1]

[0548]

[0549]

[0550]

[0551]

[0552]

[0553]

[0554]

[0555]

[0556]

[0557]

[0558]

[0559]

[0560] As shown in Table 1 above, it can be seen that the green organic EL element of Examples 1-400, which uses a mixture of compounds A-1 to E-8 and compounds F-1 to F-10 as the light-emitting layer, exhibits superior performance in terms of current efficiency, driving voltage, and lifetime characteristics compared to the green organic EL element of Comparative Example 1, which uses a mixture of compounds ET-1 (replacing compound A-1) and HT-1 (replacing compound A-1) as the light-emitting layer. This is presumably because the lone pair electrons of the heteroatom within the carbazole group of compound ET-1 are used as other migration paths for holes, thus resulting in the loss of holes equivalent to the number of holes transferred to other migration paths when excitons are formed in the light-emitting layer. In contrast, compounds A-1 to E-8 of the present invention, which use aryl groups such as phenyl or biphenyl instead of carbazole groups, do not experience exciton loss. Furthermore, due to the aryl groups, the stability of the injected electrons is improved, leading to an overall improvement in the characteristics of the element.

Claims

1. A composition for an organic electroluminescent element, comprising a first body represented by chemical formula 1 and a second body represented by chemical formula 2: [Chemical Formula 1] [Chemical Formula 2] In chemical formulas 1 and 2, a is an integer from 1 to 4. b is an integer from 0 to 3. c is an integer from 0 to 6. d and e are each integers between 0 and 5. R1 to R5 may be the same or different from each other, and each can be independently selected from deuterium (D) and C1 to C. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group and C6~C 40 The group composed of aryl groups. D stands for deuterium. Ar1 and Ar2 are each independently selected from C1 to C2. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40 aryl, heteroaryl with 5 to 40 nuclei, C1~C 40 alkoxy groups, C6~C 40 aryloxy groups, C1~C 40 alkylsilyl, C6~C 40 arylsilyl, C1~C 40 alkylboron group, C6~C 40 arylboryl group, C6~C 40 arylphosphine, C6~C 40 arylphosphine oxide and C6~C 40 The group composed of aryl amino groups. The alkyl, alkenyl, alkynyl, and aryl groups of R1 to R5 are each independently selected from deuterium (D), halogen, cyano, nitro, C1-C2. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 cycloalkyl, C6~C 40 aryl, C1~C 40 alkoxy groups, C6~C 40 aryloxy groups, C1~C 40 alkylsilyl, C6~C 40 arylsilyl, C1~C 40 alkylboron group, C6~C 40 arylboryl group, C6~C 40 arylphosphine, C6~C 40 arylphosphine oxide and C6~C 40 One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted, and when there are multiple substituents, they may be the same as or different from each other. The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphinyl, arylphosphine oxide, and arylamino groups of Ar1 and Ar2 are each independently selected from deuterium (D), halogen, cyano, nitro, C1~C1. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40 aryl groups, heteroaryl groups with 5 to 40 nuclei, C1~C 40 alkoxy groups, C6~C 40 aryloxy groups, C1~C 40 alkylsilyl, C6~C 40 arylsilyl, C1~C 40 alkylboron group, C6~C 40 arylboryl group, C6~C 40 arylphosphine, C6~C 40 arylphosphine oxide and C6~C 40 One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted, and when there are multiple substituents, they are the same as or different from each other.

2. The composition for organic electroluminescent devices according to claim 1, R1 is C6~C 40 Aryl, R4 and R5 are hydrogen, deuterium, or C6~C. 40 Aryl, The aryl groups of R1, R4, and R5 are each independently selected from deuterium (D), halogen, cyano, nitro, C1~C1. 40 Alkyl groups and C6~C 40 One or more substituents in the group consisting of aryl groups are substituted or unsubstituted, where, when there are multiple substituents, they are the same as or different from each other.

3. The composition for organic electroluminescent elements according to claim 1, wherein the first main component is a compound represented by chemical formula 3 or 4: [Chemical Formula 3] [Chemical Formula 4] In the chemical formulas 3 and 4, R2 to R5, b, c, d, and e are each identical to the definitions in claim 1. R 11 C6~C 40 Aryl, f is an integer from 0 to 3. R 12 Choose freely from hydrogen, deuterium (D), and C1~C 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group and C6~C 40 The group composed of aryl groups. The R 11 aryl and the R 12 The alkyl, alkenyl, alkynyl, and aryl groups are each independently selected from deuterium (D), halogen, cyano, nitro, C1~C2. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40 aryl groups, heteroaryl groups with 5 to 40 nuclei, C1~C 40 alkoxy groups, C6~C 40 aryloxy groups, C1~C 40 alkylsilyl, C6~C 40 arylsilyl, C1~C 40 alkylboron group, C6~C 40 arylboryl group, C6~C 40 arylphosphine, C6~C 40 arylphosphine oxide and C6~C 40 One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted, and when there are multiple substituents, they are the same as or different from each other.

4. The composition for organic electroluminescent elements according to claim 3, R 11 Substituents selected are from the group consisting of the following substituents S1-1 to S1-10. R4 and R5 may be the same as or different from each other, and each may be hydrogen or deuterium (D), or may be a substituent selected from the group consisting of the following substituents S1-1 to S1-10. The following substituents S1-1 to S1-10 are each independently substituted with deuterium (D) or not substituted: 。 5. The composition for an organic electroluminescent element according to claim 1, wherein the first main component is a compound represented by any one of the following chemical formulas 5 to 8: [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] In the chemical formulas 5 to 8, R2 to R5, b, c, d, and e are each identical to the definitions in claim 1. Dn means being replaced by n deuterium (D) units, where n is an integer greater than or equal to 1. f is an integer from 0 to 3. g is 0 or 1. R 12 Choose free deuterium (D), C1~C 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group and C6~C 40 The group composed of aryl groups. The R 12 The alkyl, alkenyl, alkynyl, and aryl groups are each independently selected from deuterium (D), halogen, cyano, nitro, C1~C2. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40 aryl groups, heteroaryl groups with 5 to 40 nuclei, C1~C 40 alkoxy groups, C6~C 40 aryloxy groups, C1~C 40 alkylsilyl, C6~C 40 arylsilyl, C1~C 40 alkylboron group, C6~C 40 arylboryl group, C6~C 40 arylphosphine, C6~C 40 arylphosphine oxide and C6~C 40 One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted, and when there are multiple substituents, they are the same as or different from each other.

6. The composition for an organic electroluminescent element according to claim 1, wherein the first main component is a compound selected from the group consisting of compounds A-1 to E-8: 。 7. The composition for an organic electroluminescent element according to claim 1, wherein the second body comprises at least 14 deuterium (D) atoms. Ar1 and Ar2 may be the same as or different from each other, and are each independently selected from C6 to C6. 40 The group consisting of aryl groups and heteroaryl groups with 5 to 40 nuclei. The aryl and heteroaryl groups of Ar1 and Ar2 are each independently selected from deuterium (D), C1~C1. 40 Alkyl groups, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40 One or more substituents from the group consisting of aryl groups and heteroaryl groups with 5 to 40 nuclei are substituted or unsubstituted, and when there are multiple substituents, they may be the same as or different from each other. in, Excluding the case where both the aryl and heteroaryl groups of Ar1 and Ar2 are replaced by deuterium (D).

8. The composition for an organic electroluminescent element according to claim 1, wherein the second main component is a compound represented by the following chemical formula 9: [Chemical Formula 9] In the chemical formula 9, Ar1 is the same as the definition in claim 1. h is 0 or 1. i is an integer from 1 to 7. D stands for deuterium. Ar3 can be chosen freely from C1 to C. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40 aryl, heteroaryl with 5 to 40 nuclei, C1~C 40 alkoxy groups, C6~C 40 aryloxy groups, C1~C 40 alkylsilyl, C6~C 40 arylsilyl, C1~C 40 alkylboron group, C6~C 40 arylboryl group, C6~C 40 arylphosphine, C6~C 40 arylphosphine oxide and C6~C 40 The group composed of aryl amino groups. The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphinyl, arylphosphine oxide, and arylamino groups of Ar3 are each independently selected from deuterium (D), halogen, cyano, nitro, C1~C1. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40 aryl groups, heteroaryl groups with 5 to 40 nuclei, C1~C 40 alkoxy groups, C6~C 40 aryloxy groups, C1~C 40 alkylsilyl, C6~C 40 arylsilyl, C1~C 40 alkylboron group, C6~C 40 arylboryl group, C6~C 40 arylphosphine, C6~C 40 arylphosphine oxide and C6~C 40 One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted, and when there are multiple substituents, they are the same as or different from each other.

9. The composition for an organic electroluminescent element according to claim 1, wherein the second main component is a compound represented by the following chemical formula 10: [Chemical Formula 10] In the chemical formula 10, Ar1 is the same as the definition in claim 1. h is 0 or 1. i is an integer from 1 to 7. D stands for deuterium. Ar3 can be chosen freely from C1 to C. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40 aryl, heteroaryl with 5 to 40 nuclei, C1~C 40 alkoxy groups, C6~C 40 aryloxy groups, C1~C 40 alkylsilyl, C6~C 40 arylsilyl, C1~C 40 alkylboron group, C6~C 40 arylboryl group, C6~C 40 arylphosphine, C6~C 40 arylphosphine oxide and C6~C 40 The group composed of aryl amino groups. The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphinyl, arylphosphine oxide, and arylamino groups of Ar3 are each independently selected from deuterium (D), halogen, cyano, nitro, C1~C1. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 40 aryl groups, heteroaryl groups with 5 to 40 nuclei, C1~C 40 alkoxy groups, C6~C 40 aryloxy groups, C1~C 40 alkylsilyl, C6~C 40 arylsilyl, C1~C 40 alkylboron group, C6~C 40 arylboryl group, C6~C 40 arylphosphine, C6~C 40 arylphosphine oxide and C6~C 40 One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted, and when there are multiple substituents, they are the same as or different from each other.

10. The composition for an organic electroluminescent element according to claim 9, wherein Ar1 and Ar3 are the same or different from each other, and each is independently a substituent selected from the group consisting of the following substituents S2-1 to S2-10: 。 11. The composition for an organic electroluminescent element according to claim 1, wherein the second main component is a compound represented by the following chemical formula 11 or 12: [Chemical Formula 11] [Chemical Formula 12] In the chemical formulas 11 and 12, Ar1 is the same as the definition in claim 1. j is 0 or 1.

12. The composition for an organic electroluminescent element according to claim 1, wherein the second main component is a compound selected from the group consisting of compounds F-1 to F-10: 。 13. The composition for an organic electroluminescent element according to claim 1, comprising the first body and the second body in a weight ratio of 99:1 to 1:

99.

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

15. The composition for organic electroluminescent elements according to claim 1, wherein the phosphorescent dopant is a metal coordination compound containing iridium (Ir) or platinum (Pt).

16. An organic electroluminescent element comprising an anode, a cathode, and one or more organic layers between the anode and the cathode. The organic layer or more comprises the composition of any one of claims 1 to 15.

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

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