Composition for organic electroluminescent device and organic electroluminescent device comprising same

Abstract

The present invention relates to a composition for an organic electroluminescent device and an organic electroluminescent device comprising same. The composition for an organic electroluminescent device comprises: a first host represented by chemical formula 1; and a second host represented by chemical formula 2, wherein the details of chemical formulas 1 and 2 are as defined in the specification.

Description

Composition for organic electroluminescent device and organic electroluminescent device comprising the same

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

[0002] In an organic electroluminescent device (hereinafter referred to as an "organic EL device"), when a voltage is applied between two electrodes, holes are injected from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. At this time, the materials used in the organic layer can be classified into light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, and electron-injecting materials depending on their function.

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

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

[0005] However, while conventional organic layer materials offer advantages in terms of luminescence characteristics, their low glass transition temperatures and poor thermal stability make them unsatisfactory in terms of lifespan in organic EL devices. Therefore, the development of high-performance organic layer materials is urgently needed.

[0006] The purpose of the present invention is to provide a composition capable of implementing a high-efficiency and long-life organic electroluminescent device.

[0007] Another object of the present invention is to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, and improved lifespan by including the aforementioned composition as an organic layer material (e.g., a luminescent layer material).

[0008] To achieve the above-mentioned purpose, the present invention provides a composition for an organic electroluminescent device comprising a first host represented by the following chemical formula 1 and a second host represented by the following chemical formula 2:

[0009]

[0010]

[0011] (In the above chemical formulas 1 and 2,

[0012] a is an integer from 1 to 4,

[0013] b is an integer from 0 to 3,

[0014] c is an integer from 0 to 6,

[0015] d and e are integers from 0 to 5, respectively,

[0016] R1 to R5 are the same or different, and each independently represents deuterium (D), C1 to C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 alkynyl group of, and C6~C 40 is selected from the group consisting of aryl groups,

[0017] D is deuterium,

[0018] Ar1 and Ar2 are each independently C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40 Aryl group of, heteroaryl group having 5 to 40 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 40 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 40 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 40 Aryl boron group, C6~C 40 Arylphosphine group, C6~C 40 Arylphosphine oxide group and C6~C 40 Selected from the group consisting of arylamine groups,

[0019] The alkyl group, alkenyl group, alkynyl group and aryl group of the above R1 to R5 are each independently deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of C6~C 40 Aryl group of C1~C 40Alkyloxy group, C6~C 40 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 40 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 40 Aryl boron group, C6~C 40 Arylphosphine group, C6~C 40 Arylphosphine oxide group and C6~C 40 is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other,

[0020] The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of the above Ar1 and Ar2 are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40 Aryl group of , heteroaryl group having 5 to 40 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 40 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 40 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 40 Aryl boron group, C6~C 40 Arylphosphine group, C6~C 40 Arylphosphine oxide group and C6~C 40 (Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other).

[0021] In addition, the present invention provides an organic electroluminescent device comprising an anode; a cathode; and at least one organic layer interposed between the anode and the cathode, wherein the at least one organic layer comprises the composition described above.

[0022] According to one embodiment of the present invention, by using a compound having strong hole properties and a compound having strong electron properties as a host, an organic electroluminescent device having low driving voltage, high efficiency, and long lifespan, as well as excellent phosphorescent emission properties, can be implemented.

[0023] The effects according to the present invention are not limited to those exemplified above, and more diverse effects are included in this specification.

[0024] FIG. 1 is a cross-sectional view showing the structure of an organic electroluminescent device according to one embodiment of the present invention.

[0025] <Explanation of symbols>

[0026] 100: positive, 200: negative,

[0027] 300: Organic layer, 310: Hole transport region,

[0028] 311: hole injection layer, 312: hole transport layer,

[0029] 320: light-emitting layer, 330: electron transport region,

[0030] 331: electron transport layer, 332: electron injection layer

[0031] The advantages and features of the present invention, and the methods for achieving them, will become clearer with reference to the embodiments described in detail below together with the accompanying drawings. However, the present invention is not limited to the embodiments disclosed below, but may be implemented in various different forms. These embodiments are provided only to ensure that the disclosure of the present invention is complete and to fully inform those skilled in the art of the scope of the invention, and the present invention is defined only by the scope of the claims. Accordingly, in some embodiments, well-known process steps, well-known device structures, and well-known techniques are not specifically described to avoid ambiguity in the interpretation of the present invention. Like reference numerals refer to like elements throughout the specification.

[0032] Unless otherwise defined, all terms (including technical and scientific terms) used herein may be used in their common sense to those of ordinary skill in the art to which the present invention pertains. Furthermore, terms defined in commonly used dictionaries are not to be interpreted ideally or excessively unless explicitly and specifically defined otherwise.

[0033] Additionally, throughout the specification, whenever a part is said to "include" a component, this does not mean that it excludes other components, but rather that it may include other components, unless otherwise specifically stated.

[0034] Additionally, throughout the specification, “above” or “on” means not only being located above or below the target part, but also including cases where there is another part in between, and does not necessarily mean being located above with respect to the direction of gravity.

[0035] In addition, the terms “first”, “second”, etc. in this specification are not used to indicate any order or importance, but are used to distinguish between components.

[0036]

[0037] <Composition for organic electroluminescent device>

[0038] The composition for an organic electroluminescent device according to the present invention is a composition for forming an organic layer (e.g., a light-emitting layer) of an organic electroluminescent device, and includes a first host represented by the above chemical formula 1, and a second host represented by the above chemical formula 2. In this case, the first host is an N-type host having relatively strong electron characteristics, and the second host is a P-type host having relatively strong hole characteristics. By using the first host and the second host together, the composition of the present invention can realize an organic electroluminescent device having high efficiency and long lifespan.

[0039] Specifically, the first host has a basic structure in which a first dibenzofuran moiety, a second dibenzofuran moiety, and a triazine moiety substituted with a diaryl group are directly connected to each other without a linker, wherein the first and second dibenzofuran moieties are bonded to each other at the 3-position of the first dibenzofuran moiety and the 2-position of the second dibenzofuran moiety, and the triazine moiety substituted with a diaryl group is introduced at the 9-position of the second dibenzofuran moiety, and is represented by the chemical formula 1. In this way, the first host can be applied as an N-type host because the first dibenzofuran moiety, the second dibenzofuran moiety, and the triazine moiety substituted with a diaryl group are bonded to each other at specific positions, thereby having a unipolar characteristic with strong electronic characteristics, the stability of the molecule can be increased, and the thermal stability can be significantly increased by generating steric hindrance of the compound.

[0040] Meanwhile, the second host has a basic structure in which two carbazole moieties are directly bonded without a linker, and the two carbazole moieties are bonded to each other at position 3, which is an active site, and the two carbazole moieties are substituted with deuterium (D), as represented by the chemical formula 2. In this way, the second host can have a high hole character and excellent molecular stability compared to a Bis-carbazole compound bonded at a different position or a Bis-carbazole compound unsubstituted with deuterium, by having the active site within the two carbazole moieties blocked by a C-C bond and substituted with deuterium (D), and therefore can be applied as a P-type host having relatively strong hole character.

[0041] The composition of the present invention including the first host and the second host described above can realize an organic electroluminescent device having low driving voltage, high efficiency, and long life characteristics, as well as excellent phosphorescent emission characteristics.

[0042] Below, the first and second hosts are described in detail.

[0043] (1) First host

[0044] In the first host represented by the above 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 integers from 0 to 5. Here, when b to e are each 0, it means that hydrogen is not substituted by the substituents R2, R3, R4, and R5, respectively. 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 integers from 1 to 5, it means that hydrogen is substituted by the substituents R1, R2, R3, R4, and R5, respectively. At this time, in the present invention, when at least one of R1, R2, R3, R4 and R5 is a functional group containing a hetero atom, it was recognized that the unshared electron pair of the hetero atom can be used as another movement path of holes, and thus, when forming excitons in the light-emitting layer, fewer excitons are generated by the number of holes transferred to another movement path, thereby reducing efficiency. Accordingly, in the present invention, a functional group containing a non-heteroatom is selectively introduced as R1, R2, R3, R4 and R5 of Chemical Formula 1. In particular, R1, R2, R3, R4 and R5, Specifically, when R1, R4 and R5 are aryl groups, the stability to electrons can be further improved. Therefore, one or more R1, R2, R3, R4 and R5 are the same or different from each other, and each independently represents deuterium (D), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 alkynyl group of, and C6~C 40 is selected from the group consisting of aryl groups.

[0045] The alkyl group, alkenyl group, alkynyl group and aryl group of the above R1 to R5 are each independently deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C40 Alkynyl group, C3~C 40 Cycloalkyl group of C6~C 40 Aryl group of C1~C 40 Alkyloxy group, C6~C 40 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 40 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 40 Aryl boron group, C6~C 40 Arylphosphine group, C6~C 40 Arylphosphine oxide group and C6~C 40 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and specifically, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group, and C6~C 40 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of aryl groups. In this case, when there are multiple substituents, they are the same or different from each other.

[0046] For example, R1 is C6~C 40 is an aryl group, and R4 and R5 are each independently hydrogen, deuterium (D), or C6~C 40 It may be an aryl group of. At this time, the aryl groups of R1, R4 and R5 are each independently deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group, and C6~C 40 It is substituted or unsubstituted with one or more substituents selected from the group consisting of aryl groups, and when there are multiple substituents, they may be the same or different from each other.

[0047] Also, in the first host, the first dibenzofuran moiety ( ) is introduced at positions 6 to 9, preferably 6 or 9, not only does the glass transition temperature increase, but the morphology is uniform, resulting in high crystallinity and packing density, so that the thermal stability and electron transport properties of the first host can be further improved.

[0048] Such a first host may be a compound represented by the following chemical formula 3 or 4.

[0049]

[0050]

[0051] In the above chemical formulas 3 and 4,

[0052] R2 to R5, b, c, d and e are each as defined in the above chemical formula 1,

[0053] R 11 Silver C6~C 40 is an aryl group,

[0054] f is an integer from 0 to 3,

[0055] Multiple R's 12 are identical or different from each other,

[0056] R 12 is deuterium (D), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 alkynyl group of, and C6~C 40 is selected from the group consisting of aryl groups, and may be specifically deuterium (D),

[0057] The above R 11 Aryl group of and the above R 12 The alkyl group, alkenyl group, alkynyl group and aryl group are each independently deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40 Aryl group of , heteroaryl group having 5 to 40 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 40 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 40 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 40 Aryl boron group, C6~C 40 Arylphosphine group, C6~C 40 Arylphosphine oxide group and C6~C 40 It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other.

[0058] For example, in the chemical formulas 3 and 4, R 11 is a substituent selected from the group consisting of the following substituents S1-1 to S1-10; R4 and R5 are the same or different, and each independently represent hydrogen or deuterium (D), or may be a substituent 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 may each independently be substituted with or unsubstituted by deuterium (D).

[0059]

[0060] In the above substituents S1-1 to S1-10,

[0061] * is a part connected to the above chemical formula 3 or 4.

[0062] The above first host may be a compound represented by any one 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, the number thereof, or the substitution position, but is not limited thereto.

[0063]

[0064]

[0065]

[0066]

[0067] In the above chemical formulas 5 to 8,

[0068] R2 to R5, b, c, d and e are each as defined in the above chemical formula 1,

[0069] Dn means that it is replaced by n deuterium atoms (D), n is an integer of 1 or more, specifically n is an integer from 1 to 35,

[0070] f is an integer from 0 to 3,

[0071] g is 0 or 1,

[0072] R 12 is deuterium (D), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 alkynyl group of, and C6~C 40 is selected from the group consisting of aryl groups,

[0073] The above R 12 The alkyl group, alkenyl group, alkynyl group and aryl group are each independently deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40 Aryl group of , heteroaryl group having 5 to 40 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 40 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 40 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 40Aryl boron group, C6~C 40 Arylphosphine group, C6~C 40 Arylphosphine oxide group and C6~C 40 It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they may be the same or different from each other.

[0074] The first host represented by the chemical formula 1 according to the present invention described above can be further specified by the following exemplary compounds, for example, compounds A-1 to E-8, but is not limited thereto.

[0075]

[0076]

[0077]

[0078] (2) Second host

[0079] Since the second host according to the present invention has high stability of chemical structure through deuterium (D) substitution, by using it in combination with the first host, the characteristics of an organic electroluminescent device, such as low voltage, high efficiency, and long lifespan of the device, can be simultaneously implemented.

[0080] According to an example, the number of deuterium (D) included in the second host is at least 14, and specifically, may be 14 to 21, and Ar1 and Ar2 are the same or different from each other, and are each independently C6 to C 40 It can be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 40 nuclear atoms. At this time, the aryl group and heteroaryl group of Ar1 and Ar2 are each independently deuterium (D), C1~C 40 Alkyl group of C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40It is unsubstituted or substituted with at least one substituent selected from the group consisting of an aryl group and a heteroaryl group having 5 to 40 nuclear atoms, and when there are multiple substituents, they are the same or different from each other, but it is preferable to exclude the case where both the aryl group and the heteroaryl group of Ar1 and Ar2 are substituted with deuterium (D).

[0081] Also, in the second host represented by the above chemical formula 2, Ar1 and Ar2 are the same or different from each other, and are each independently C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40 Aryl group of, heteroaryl group having 5 to 40 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 40 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 40 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 40 Aryl boron group, C6~C 40 Arylphosphine group, C6~C 40 Arylphosphine oxide group and C6~C 40 Selected from the group consisting of arylamine groups, and specifically, each independently C1~C 40 Alkyl group of C6~C 40 Aryl group of, heteroaryl group of 5 to 40 nuclear atoms and C6~C 40 It can be selected from the group consisting of arylamine groups.

[0082] The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of the above Ar1 and Ar2 are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40 Aryl group of , heteroaryl group having 5 to 40 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 40 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 40 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 40 Aryl boron group, C6~C 40 Arylphosphine group, C6~C 40 Arylphosphine oxide group and C6~C 40 It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other.

[0083] According to an example, Ar1 and Ar2 are the same or different from each other, and can be independently selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a quarterphenyl group, and a carbazole group. In this case, the phenyl group, the biphenyl group, the naphthyl group, the terphenyl group, the quarterphenyl group, and the carbazole group are each independently selected from the group consisting of deuterium (D), C1~C 40 Alkyl group of C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40It is substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 40 nuclear atoms, and when there are multiple substituents, they may be the same or different from each other.

[0084] According to another example, Ar1 is selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, and a quarterphenyl group, and Ar2 is the same as or different from Ar1 and may be selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a quarterphenyl group, and a carbazole group. In this case, the phenyl group, the biphenyl group, the naphthyl group, the terphenyl group, the quarterphenyl group, and the carbazole group may be selected from the group consisting of deuterium (D), C1~C 40 Alkyl group of C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40 It is substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 40 nuclear atoms, and when there are multiple substituents, they may be the same or different from each other.

[0085] According to another example, Ar1 is selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, and a quarterphenyl group, and Ar2 is the same as or different from Ar1 and may be selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, and a quarterphenyl group. In this case, the phenyl group, the biphenyl group, the naphthyl group, the terphenyl group, and the quarterphenyl group may be selected from the group consisting of deuterium (D), C1~C 40 Alkyl group of C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40 It is substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 40 nuclear atoms, and when there are multiple substituents, they may be the same or different from each other.

[0086] In addition, the second host may be a compound represented by the following chemical formula 9, depending on whether Ar2 is a carbazole group or a non-carbazole group.

[0087]

[0088] In the above chemical formula 9,

[0089] Ar1 is as defined in the above chemical formula 1, and specifically C6~C 40 It can be an aryl group,

[0090] h is 0 or 1,

[0091] i is an integer from 1 to 7, specifically an integer of 1 or 7,

[0092] D is deuterium,

[0093] Ar3 is C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40 Aryl group of, heteroaryl group having 5 to 40 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 40 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 40 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 40 Aryl boron group, C6~C 40 Arylphosphine group, C6~C 40 Arylphosphine oxide group and C6~C 40 Selected from the group consisting of arylamine groups, specifically C6~C 40 It can be an aryl group,

[0094] The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of the above Ar3 are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40 Aryl group of , heteroaryl group having 5 to 40 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 40 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 40 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 40 Aryl boron group, C6~C 40 Arylphosphine group, C6~C 40 Arylphosphine oxide group and C6~C 40 It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they may be the same or different from each other.

[0095] Also, when h is 1 in the above chemical formula 9, the second host is a third carbazole moiety ( ) can have various structures depending on the bonding position. However, when three carbazole moieties are bonded to each other at position 3, which is the active site, the active site is blocked by a CC bond, so it can have high hole properties and excellent molecular stability compared to Tri-carbazole compounds bonded at other positions. This second host can be a compound represented by the following chemical formula 10.

[0096]

[0097] In the above chemical formula 10,

[0098] Ar1 is as defined in the above chemical formula 1, and specifically C6~C 40 It can be an aryl group,

[0099] h is 0 or 1,

[0100] i is an integer from 1 to 7, specifically an integer of 1 or 7,

[0101] D is deuterium,

[0102] Ar3 is C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40 Aryl group of, heteroaryl group having 5 to 40 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 40 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 40 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 40 Aryl boron group, C6~C 40 Arylphosphine group, C6~C 40 Arylphosphine oxide group and C6~C 40 Selected from the group consisting of arylamine groups, specifically C6~C 40 It can be an aryl group,

[0103] The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of the above Ar3 are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40 Aryl group of , heteroaryl group having 5 to 40 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 40 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 40 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 40 Aryl boron group, C6~C 40 Arylphosphine group, C6~C 40 Arylphosphine oxide group and C6~C 40 It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they may be the same or different from each other.

[0104] For example, in the chemical formula 10, Ar1 and Ar3 may be the same as or different from each other, and may each independently be a substituent selected from the group consisting of the following substituents S2-1 to S2-10.

[0105]

[0106] In the above substituents S2-1 to S2-10, * is a moiety connected to the above chemical formula 10.

[0107] In addition, the second host may be a compound represented by the following chemical formula 11 or 12 depending on Ar2, but is not limited thereto.

[0108]

[0109]

[0110] In the above chemical formulas 11 and 12,

[0111] Ar1 is as defined in the above chemical formula 1, and specifically C6~C 40It may be an aryl group, and more specifically, it may be a substituent selected from the group consisting of the substituents S2-1 to S2-10,

[0112] j is either 0 or 1.

[0113] The second host according to the present invention described above can be further specified by the following exemplary compounds, for example, compounds F-1 to F-10, but is not limited thereto.

[0114]

[0115] In the present invention, "alkyl" means a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, etc.

[0116] In the present invention, "alkenyl" means a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, and 2-butenyl.

[0117] In the present invention, "alkynyl" means a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

[0118] In the present invention, "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

[0119] In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon atom, preferably 1 to 3 carbons in the ring, is substituted with a heteroatom such as N, O, S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.

[0120] In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or a combination of two or more rings. Furthermore, a form in which two or more rings are simply attached to each other (pendant) or condensed may also be included. Examples of such aryls include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

[0121] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon atom in the ring, preferably 1 to 3 carbon atom, is substituted with a heteroatom such as N, O, S, or Se. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may be included, and a form condensed with an aryl group may also be included. Examples of such heteroaryls include, but are not limited to, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl.

[0122] In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms, and may include a linear, branched, or cyclic structure. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

[0123] In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

[0124] In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and includes not only mono- but also di- and tri-alkylsilyl. In addition, "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms, and includes not only mono- but also polyarylsilyl such as di- and tri-arylsilyl.

[0125] In the present invention, “alkylboron group” means a boron group substituted with an alkyl having 1 to 40 carbon atoms, and “arylboron group” means a boron group substituted with an aryl having 6 to 60 carbon atoms.

[0126] In the present invention, "alkylphosphinyl group" means a phosphine group substituted with an alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-alkylphosphinyl groups. In addition, "arylphosphinyl group" in the present invention means a phosphine group substituted with a monoaryl or diaryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylphosphinyl groups.

[0127] In the present invention, “arylamine” means an amine substituted with an aryl having 6 to 60 carbon atoms, and includes not only mono- but also di-arylamine.

[0128] In the present invention, “heteroarylamine” means an amine substituted with a heteroaryl having 5 to 60 nuclear atoms, and includes not only mono- but also di-heteroarylamine.

[0129] In the present invention, (aryl)(heteroaryl)amine means an amine substituted with an aryl having 6 to 60 carbon atoms and a heteroaryl having 5 to 60 nuclear atoms.

[0130] In the present invention, “fused ring” means a fused aliphatic ring having 3 to 40 carbon atoms, a fused aromatic ring having 6 to 60 carbon atoms, a fused heteroaliphatic ring having 3 to 60 nuclear atoms, a fused heteroaromatic ring having 5 to 60 nuclear atoms, a spiro ring having 3 to 60 carbon atoms, or a combination thereof.

[0131] The first host and the second host described above may be included in a weight ratio of 99:1 to 1:99, specifically, a weight ratio of 20:80 to 80:20. In this case, bipolar characteristics can be more effectively implemented, thereby simultaneously improving efficiency and lifespan.

[0132] The composition of the present invention may additionally include a phosphorescent dopant. The phosphorescent dopant is a material that causes light emission when mixed in a small amount with the first and second hosts. Any material known in the art is not particularly limited, and non-limiting examples thereof include metal complex compounds containing iridium (Ir) or platinum (Pt). Such dopants can cause light emission by multiple excitation that excites to a triplet state or higher.

[0133] The above dopants can be classified into red dopants, green dopants and blue dopants, and red dopants, green dopants and blue dopants commonly known in the art can be used without particular limitation.

[0134] 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.

[0135] Additionally, 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.

[0136] Additionally, non-limiting examples of blue dopants include F2Irpic (Bis[3,5-difluoro-2-(2-pyridyl)phenyl](picolinato)iridium(III): bis[3,5-difluoro-2-(2-pyridyl)phenyl(picolinato)iridium(III)), (F2ppy)2Ir(tmd), Ir(dfppz)3, or mixtures of two or more thereof.

[0137] The content of the above-mentioned dopant is not particularly limited, and may be, for example, about 0 to 30 wt%, specifically about 0.1 to 15 wt%, and more specifically about 1 to 10 wt%, based on the total amount of the above-mentioned composition. In this case, the total content of the first host and the second host may be about 70 to 100 wt%, specifically about 85 to 99.9 wt%, and more specifically about 90 to 99 wt%, based on the total amount of the composition.

[0138]

[0139] Organic electroluminescent devices

[0140] An organic electroluminescent device according to one embodiment of the present invention comprises an anode; a cathode; and at least one organic layer interposed between the anode and the cathode, wherein the at least one organic layer comprises the aforementioned composition. In one example, the at least one organic layer comprises a light-emitting layer, and the composition may be included as a host for the light-emitting layer. Accordingly, the organic electroluminescent device of the present invention not only has low driving voltage, high efficiency, and long life characteristics, but also exhibits excellent phosphorescent emission characteristics.

[0141] Hereinafter, preferred embodiments of an organic electroluminescent device according to the present invention will be described with reference to the attached drawings. However, the embodiments of the present invention may be modified in various other forms, and the scope of the present invention is not limited to the embodiments described below. To avoid duplication, descriptions of the components described in the composition for the organic electroluminescent device described above will be omitted.

[0142] FIG. 1 is a cross-sectional view schematically showing the structure of an organic electroluminescent device according to one embodiment of the present invention.

[0143] Referring to FIG. 1, an organic electroluminescent device according to one embodiment of the present invention includes an anode (100) disposed on a substrate (not shown); a cathode (200) disposed opposite the anode; and one or more organic layers (300) between the anode (100) and the cathode (200), wherein the one or more organic layers (300) may include a hole transport region (310), a light-emitting layer (320), and an electron transport region (330). At this time, the light-emitting layer (320) may include the above-described composition as a host. Optionally, the organic electroluminescent device of the present invention may further include a capping layer (not shown) disposed on the cathode (200).

[0144] Hereinafter, each component of the organic electroluminescent device according to the present invention will be examined in detail.

[0145] (1) Anode

[0146] In the organic electroluminescent device of the present invention, the anode (100) is mainly disposed on the substrate, and is electrically connected to the driving thin film transistor so that it can receive driving current from the driving thin film transistor. Since the anode (100) is formed of a material having a relatively high work function, it injects holes into the organic layer (300), i.e., the hole transport region (310) [e.g., the hole injection layer (311)].

[0147] The material forming such an anode is not particularly limited, and a conventional material known in the art can be used. For example, there are, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold; alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al, SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDT), polypyrrole, and polyaniline; and carbon black.

[0148] The method for manufacturing the above anode is not particularly limited, and can be manufactured using conventional methods known in the art. For example, the anode material can be formed by coating it on a substrate using a known thin film forming method such as sputtering, ion plating, vacuum deposition, or spin coating.

[0149] The above substrate is a plate-shaped member that supports an organic electroluminescent element, and examples thereof include, but are not limited to, a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, and a sheet.

[0150] (2) Cathode

[0151] In the organic electroluminescent device of the present invention, the cathode (200) is an electrode positioned opposite the anode, and is specifically positioned on the electron transport region (330). Since the cathode (200) is made of a material having a relatively low work function, it injects electrons into an adjacent organic layer, i.e., the electron transport region (330) [e.g., the electron injection layer (332)].

[0152] The material forming the cathode is not particularly limited, and conventional materials known in the art can be used. Examples thereof include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin, and lead; alloys thereof; and multilayered materials such as LiF / Al and LiO2 / Al.

[0153] The method for manufacturing the above 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 formed by coating it on one or more organic layers (300), specifically, an electron transport region, such as an electron injection layer (332), using the aforementioned thin film formation method.

[0154] (3) Organic layer

[0155] In the organic electroluminescent device of the present invention, one or more organic layers (300) are disposed between the anode (100) and the cathode (200), and include a hole transport region (310), a light-emitting layer (320), and an electron transport region (330).

[0156] According to an example, as illustrated in FIG. 1, 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 arranged on an anode (100).

[0157] Below, each organic layer is described.

[0158] 1) Hole transport region

[0159] In the organic electroluminescent device (100) of the present invention, the hole transport region (310) is a part of the organic layer (300) disposed on the anode (100), and serves to move holes injected from the anode (100) to the adjacent light-emitting layer (320).

[0160] This hole transport region (310) may include at least one selected from the group consisting of a hole injection layer (311) and a hole transport layer (312). At this time, considering the characteristics of the organic electroluminescent device, it is preferable to include both the hole injection layer (311) and the hole transport layer (312) described above. For example, the hole transport region (310) may include a hole injection layer (311) and a hole transport layer (312) sequentially stacked on an anode (100), as illustrated in FIG. 1.

[0161] The materials forming 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 high hole mobility, and any hole injection layer / transport layer material used in the art can be used without limitation. In this case, the materials forming the hole injection layer (311) and the hole transport layer (312) may be the same or different from each other.

[0162] Specifically, the hole injection layer (311) includes a hole injection material known in the art. Non-limiting examples of the hole injection material include phthalocyanine compounds such as copper phthalocyanine; DNTPD (N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine), m-MTDATA (4,4',4"-tris(3-methylphenylphenylamino) triphenylamine), TDATA(4,4'4"-Tris(N,N-diphenylamino)triphenylamine), 2TNATA(4,4',4"-tris{N,-(2-naphthyl)-N-phenylamino}-triphenylamine), PEDOT / PSS(Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate)), PANI / DBSA (Polyaniline / Dodecylbenzenesulfonic acid), PANI / CSA (Polyaniline / Camphor sulfonicacid), PANI / PSS ((Polyaniline) / Poly(4-styrenesulfonate)), etc. It can be used, or two or more types can be mixed and used.

[0163] The above hole transport layer (312) includes a hole transport material known in the art. Non-limiting examples of the hole transport material include carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole; fluorene derivatives; amine derivatives; triphenylamine derivatives such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine), TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine); NPB (N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine), TAPC (4,4'-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), etc. These may be used alone or in a mixture of two or more.

[0164] The above-mentioned hole transport region (310) can be manufactured using a conventional method known in the art. Examples thereof include, but are not limited to, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) printing, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0165] 2) Emissive layer

[0166] In the organic electroluminescent device of the present invention, the light-emitting layer (320) is a part of the organic layer (300) interposed between the anode (100) and the cathode (200), and is specifically disposed on the hole transport region (320). As illustrated in FIG. 1, the light-emitting layer (320) may be disposed on the hole transport layer (312).

[0167] This light-emitting layer (320) is a layer in which holes and electrons injected from the anode and cathode, respectively, combine to form excitons, and the color of light emitted by the organic electroluminescent element may vary depending on the material forming the light-emitting layer (320).

[0168] The light-emitting layer (320) according to the present invention comprises a composition containing a first host represented by the above-described chemical formula 1 and a second host represented by the above-described chemical formula 2. The composition may optionally further contain a phosphorescent dopant. By including the above-described composition as a material for the light-emitting layer (320), the organic electroluminescent device of the present invention can exhibit excellent phosphorescent emission characteristics as well as low driving voltage, high efficiency, and long lifespan characteristics.

[0169] The light-emitting layer (320) according to the present invention may be a red light-emitting layer including a red phosphorescent material; a green light-emitting layer including a green phosphorescent material; or a blue light-emitting layer including a blue phosphorescent material. In one example, it may be a light-emitting layer including a green phosphorescent material.

[0170] The aforementioned light-emitting layer (320) may be formed of a single layer made of one type of material, a single layer made of a plurality of different materials, or two or more layers in which each layer is made of a different material. Here, when the light-emitting layer (320) is formed of a plurality of layers, the organic electroluminescent device can emit light of various colors. Specifically, the present invention can provide an organic electroluminescent device having mixed colors by having a plurality of light-emitting layers made of different materials in series. In addition, when a plurality of light-emitting layers are included, the driving voltage of the device increases, while the current value within the organic electroluminescent device becomes constant, thereby providing an organic electroluminescent device in which the light-emitting efficiency is improved by the number of light-emitting layers.

[0171] Although not shown in the drawing, the organic electroluminescent device of the present invention may have a plurality of light-emitting stacks (not shown) each including at least one light-emitting layer.

[0172] The plurality of light-emitting layers included in the light-emitting stack may be light-emitting layers that each emit light of a different color or light-emitting layers that emit light of the same color. That is, the light-emitting color may vary depending on the material that constitutes the light-emitting layer. For example, the plurality of light-emitting stacks may include materials that emit light of blue, green, red, yellow, white, etc., and may be formed using a phosphorescent or fluorescent material. In this case, the colors exhibited by each light-emitting layer may be complementary to each other. In addition, the color may be selected as a combination of colors that can emit white light. Each of the light-emitting layers may include phosphorescent dopants or fluorescent dopants corresponding to the selected color, respectively.

[0173] Although not shown in the drawing, the organic electroluminescent device of the present invention may further include a charge generation layer (CGL) (not shown) disposed between adjacent stacks among a plurality of light-emitting stacks to connect them.

[0174] A charge generation layer (CGL) is a layer that separates adjacently arranged light-emitting stacks without directly contacting both electrodes (e.g., anode, cathode) in an organic electroluminescent device having a plurality of light-emitting stacks. The charge generation layer is arranged between two adjacent light-emitting stacks, and acts as a cathode that generates and supplies electrons to one light-emitting stack, and acts as an anode that generates and supplies holes to the other light-emitting stack. The charge generation layer may be formed by using any material known in the art as a charge generation layer material without limitation. In addition, the charge generation layer may be formed by doping a material known in the art with a conventional n-type material and / or p-type material.

[0175] The aforementioned light-emitting layer (320) can be manufactured using a conventional method known in the art. For example, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, laser induced thermal imaging (LITI), etc., are available, but are not limited thereto. For example, the light-emitting layer can be formed by co-deposition of a first host represented by the above chemical formula 1 and a second host represented by the above chemical formula 2. At this time, a dopant can also be co-deposited.

[0176] 3) Electron transport region

[0177] In the organic electroluminescent device according to the present invention, the electron transport region (330) is an organic layer disposed on the light-emitting layer (320), and moves electrons injected from the cathode (200) to the light-emitting layer (320).

[0178] This electron transport region (330) may include at least one selected from the group consisting of an electron transport layer (331) and an electron injection layer (332).

[0179] For example, the electron transport region (330) may include an electron transport layer (331) and an electron injection layer (332) sequentially stacked on the light-emitting layer (320), as illustrated in FIG. 1.

[0180] In the electron transport region (330) according to the present invention, the electron transport layer (331) can be used without limitation as long as it is an electron transport material that is easy to inject electrons and has high electron mobility. 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 may be used alone or in a mixture of two or more.

[0181] In addition, the electron injection layer (332) can use an electron injection material that is easy to inject electrons and has high electron mobility without limitation. Non-limiting examples of the electron injection material include LiF, Li2O, BaO, NaCl, CsF; lanthanide metals such as Yb; or halogenated metals such as RbCl, RbI, etc., which can be used alone or in a mixture of two or more.

[0182] The electron transport region (330) according to the present invention, specifically the electron transport layer (331) and / or the electron injection layer (332), may be co-deposited with an n-type dopant to facilitate injection of electrons from the cathode (200). At this time, the n-type dopant may be any alkali metal complex known in the art without limitation, and examples thereof include alkali metals, alkaline earth metals, or rare earth metals.

[0183] The above electron transport region (330) can be manufactured using a conventional method known in the art. Examples thereof include, but are not limited to, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) printing, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0184] 4) Luminescent auxiliary layer

[0185] Although not shown, the organic electroluminescent device of the present invention may additionally include a light-emitting auxiliary layer disposed between the hole transport region (310) and the light-emitting layer (320).

[0186] The light-emitting auxiliary layer serves to control the thickness of the organic layer (300) by transporting holes moved from the hole transport region (310) to the light-emitting layer (320) or by blocking the movement of electrons and / or excitons. In particular, the light-emitting auxiliary layer has a high LUMO value to prevent electrons from moving to the hole transport layer (312), and has a high triplet energy to prevent excitons of the light-emitting layer (320) from diffusing to the hole transport layer (312).

[0187] These light-emitting auxiliary layers may include a hole transport material and may be made of the same material as the hole transport region. Furthermore, the light-emitting auxiliary layers of the red, green, and blue organic electroluminescent devices may be made of the same material.

[0188] There are no particular limitations on the light-emitting auxiliary layer material, and examples thereof include carbazole derivatives, arylamine derivatives, etc. Specifically, examples of the light-emitting auxiliary layer include, but are not limited to, NPD (N, N-dinaphthyl-N, N'-diphenyl benzidine), TPD (N, N'-bis-(3-methylphenyl)-N, N'-bis(phenyl)- benzidine), s-TAD, MTDATA (4, 4', 4″-Tris(N-3-methylphenyl-Nphenyl-amino)- triphenylamine), etc. These may be used alone or in a mixture of two or more.

[0189] In addition, the light-emitting auxiliary layer may further include a p-type dopant in addition to the aforementioned materials. As the p-type dopant usable in the present invention, any known p-type dopant commonly used in the relevant technical field may be used without particular limitation. In this case, the content of the p-type dopant may be appropriately adjusted within a range known in the relevant technical field, and may be, for example, about 0.5 to 50 parts by weight based on 100 parts by weight of the hole transport material.

[0190] The above-mentioned light-emitting auxiliary layer can be formed by, but is not limited to, a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett method, an inkjet printing method, a laser printing method, a laser induced thermal imaging (LITI) method, etc., as is known in the art.

[0191] 5) Static blocking layer

[0192] Although not shown, the organic electroluminescent device (100) of the present invention may additionally include a hole blocking layer disposed between the light emitting layer (320) and the electron transport region (330).

[0193] The above hole blocking layer (333) can improve the lifespan of the organic electroluminescent device by preventing excitons or holes generated in the light-emitting layer (320) from diffusing (moving) to the electron transport layer (331).

[0194] The material of the hole-blocking layer may be any material known in the art with conventional electron transport properties, without limitation, and may include, for example, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), bis(2-methyl-8-quinolinolato)(4-phenyl-phenolato)aluminum(III)(BAlq), etc.

[0195] The above hole-blocking layer can be formed by, but is not limited to, a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett method, an inkjet printing method, a laser printing method, a laser induced thermal imaging (LITI) method, etc., as is known in the art.

[0196] (4) Capping layer

[0197] Optionally, the organic electroluminescent device (100) of the present invention may further include a capping layer (not shown) disposed on the cathode (200) described above.

[0198] The capping layer protects the organic electroluminescent element and helps light generated from the organic layer to be efficiently emitted to the outside.

[0199] The capping layer may include at least one selected from the group consisting of tris-8-hydroxyquinoline aluminum (Alq3), ZnSe, 2,5-bis(6′-(2′,2″-bipyridyl))-1,1-dimethyl-3,4-diphenylsilole, 4′-bis[N-(1-napthyl)-N- phenyl-amion] biphenyl (α-NPD), N,N′-diphenyl-N,N′-bis(3-methylphenyl) -1,1′-biphenyl-4,4′-diamine (TPD), 1,1′-bis(di-4-tolylaminophenyl) cyclohexane (TAPC). The material forming the capping layer is inexpensive compared to materials of other layers of the organic electroluminescent device.

[0200] This capping layer may be a single layer, but may include two or more layers having different refractive indices, such that the refractive index gradually changes as the material passes through the two or more layers.

[0201] The above capping layer can be manufactured by a conventional method known in the art, and various methods such as vacuum deposition, spin coating, casting, or LB (Langmuir-Blodgett) method can be used, for example.

[0202] The organic electroluminescent device according to the present invention has a structure in which an anode (100), an organic layer (300), and a cathode (200) are sequentially laminated. In some cases, 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) may be further included. The organic electroluminescent device of the present invention may have excellent life characteristics because the half-life time of the initial brightness is increased while maintaining maximum luminous efficiency when voltage and current are applied.

[0203] The organic electroluminescent device of the present invention described above can be manufactured according to a conventional method known in the art. For example, an organic electroluminescent device can be manufactured by vacuum-depositing an anode material on a substrate, and then sequentially vacuum-depositing materials for a hole transport region material, an emission layer material, an electron transport region material, and a cathode material on the anode.

[0204]

[0205] Hereinafter, the present invention will be described in detail through examples. However, the following examples are only illustrative of the present invention, and the present invention is not limited to the following examples.

[0206] [Preparation Example 1] Synthesis of compound DDB-1

[0207] <Step 1> Synthesis of 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane

[0208]

[0209] Under a nitrogen stream, 7-chloro-1-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (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 h.

[0210] After the reaction was completed, the organic layer was extracted with ethyl acetate, and then moisture was removed from the organic layer with MgSO4, and 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-dioxaborolane (97.0 g, yield 73%).

[0211] Mass (theoretical: 370.26, measured: 370 g / mol)

[0212] <Step 2> Synthesis of 9-chloro-9'-phenyl-2,3'-bidibenzo[b,d]furan

[0213]

[0214] Under a nitrogen stream, 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane (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 h.

[0215] After the reaction was completed, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane:DCM = 9:1 (v / v)) to obtain 9'-chloro-9-phenyl-2,3'-bidibenzo[b,d]furan (72.2 g, yield 62%).

[0216] Mass (theoretical: 444.91, measured: 444 g / mol)

[0217] <Step 3> Synthesis of compound DDB-1

[0218]

[0219] Under a nitrogen stream, 9'-chloro-9-phenyl-2,3'-bidibenzo[b,d]furan (72.2 g, 162.4 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (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 h.

[0220] After the reaction was completed, the organic layer was extracted with ethyl acetate, and then moisture was removed from the organic layer with MgSO4, and the organic layer was purified by column chromatography (Hexane:EA = 8:1 (v / v)) to obtain DDB-1 (54.9 g, yield 63%).

[0221] Mass (theoretical: 536.43, measured: 536 g / mol)

[0222]

[0223] [Preparation Example 2] Synthesis of compound DDB-2

[0224] <Step 1>

[0225]

[0226] The target compound was obtained by performing the same procedure as in Step 1 of Preparation Example 1, except that 3-chloro-6-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) was used instead of 7-chloro-1-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) used in Step 1 of Preparation Example 1.

[0227] Step 2

[0228]

[0229] The target compound was obtained by performing the same process as step 2 of preparation example 1, except that the target compound obtained in step 1 of preparation example 2 was used instead of 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane used in step 2 of preparation example 1.

[0230] <Step 3> - Synthesis of compound DDB-2

[0231]

[0232] The same procedure as step 3 of preparation example 1 was followed, except that the target compound obtained in step 2 of preparation example 2 was used instead of 9'-chloro-9-phenyl-2,3'-bidibenzo[b,d]furan used in step 3 of preparation example 1, to obtain the target compound DDB-2 (71.8 g, final yield 37.3%).

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

[0234]

[0235] [Preparation Example 3] Synthesis of compound DDB-3

[0236] <Step 1>

[0237]

[0238] The target compound was obtained by performing the same procedure as in Step 1 of Preparation Example 1, except that 1-([1,1'-biphenyl]-4-yl)-7-chlorodibenzo[b,d]furan (100.0 g, 282.4 mmol) was used instead of 7-chloro-1-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) used in Step 1 of Preparation Example 1.

[0239] Step 2

[0240]

[0241] The target compound was obtained by performing the same process as step 2 of preparation example 1, except that the target compound obtained in step 1 of preparation example 3 was used instead of 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane used in step 2 of preparation example 1.

[0242] <Step 3> - Synthesis of compound DDB-3

[0243]

[0244] The same procedure as step 3 of preparation example 1 was followed, except that the target compound obtained in step 2 of preparation example 3 was used instead of 9'-chloro-9-phenyl-2,3'-bidibenzo[b,d]furan used in step 3 of preparation example 1, to obtain the target compound DDB-3 (48.2 g, final yield 27.8%).

[0245] Mass (theoretical: 612.53, measured: 612 g / mol)

[0246]

[0247] [Preparation Example 4] Synthesis of compound DDB-4

[0248] <Step 1>

[0249]

[0250] The target compound was obtained by performing the same procedure as in Step 1 of Preparation Example 1, except that 7-chloro-1-(phenyl-d5)dibenzo[b,d]furan-2,3,4,6,8,9-d6 (100.0 g, 345.1 mmol) was used instead of 7-chloro-1-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) used in Step 1 of Preparation Example 1.

[0251] Step 2

[0252]

[0253] The same procedure as in Step 2 of Preparation Example 1 was followed, except that the target compound obtained in Step 1 of Preparation Example 4 was used instead of 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane used in Step 2 of Preparation Example 1, and 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), to obtain the target compound.

[0254] <Step 3> - Synthesis of compound DDB-4

[0255]

[0256] The same procedure as step 3 of preparation example 1 was followed, except that the target compound obtained in step 2 of preparation example 4 was used instead of 9'-chloro-9-phenyl-2,3'-bidibenzo[b,d]furan used in step 3 of preparation example 1, to obtain the target compound DDB-4 (37.5 g, final yield 19.7%).

[0257] Mass (theoretical: 553.54, measured: 553 g / mol)

[0258]

[0259] [Preparation Example 5] Synthesis of compound DDB-5

[0260] <Step 1>

[0261]

[0262] The target compound was obtained by performing the same procedure as in Step 1 of Preparation Example 1, except that 3-chloro-6-(phenyl-d5)dibenzo[b,d]furan-1,2,4,7,8,9-d6 (100.0 g, 345.1 mmol) was used instead of 7-chloro-1-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) used in Step 1 of Preparation Example 1.

[0263] Step 2

[0264]

[0265] The same procedure as in Step 2 of Preparation Example 1 was followed, except that the target compound obtained in Step 1 of Preparation Example 5 was used instead of 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane 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 instead of 8-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol), to obtain the target compound.

[0266] <Step 3> - Synthesis of compound DDB-5

[0267]

[0268] The same process as step 3 of preparation example 1 was performed except that the target compound obtained in step 2 of preparation example 5 was used instead of 9'-chloro-9-phenyl-2,3'-bidibenzo[b,d]furan used in step 3 of preparation example 1, thereby obtaining the target compound DDB-5 (41.2 g, final yield 21.6%).

[0269] Mass (theoretical: 553.54, measured: 553 g / mol)

[0270]

[0271] [Synthesis Example 1] Synthesis of Compound A-1

[0272]

[0273] Under a nitrogen stream, compound DDB-1 (10.0 g, 18.6 mmol) obtained in Preparation Example 1, 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) were mixed and stirred at 120°C for 4 hours.

[0274] After the reaction was completed, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:EA = 4:1 (v / v)) to obtain the target compound A-1 (7.8 g, yield 65%).

[0275] Mass (theoretical: 641.73, measured: 641 g / mol)

[0276]

[0277] [Synthesis Example 2] Synthesis of Compound A-2

[0278]

[0279] The same procedure as in Synthesis Example 1 was followed, except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.2 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1, to obtain the target compound A-2 (7.4 g, yield 61%).

[0280] Mass (theoretical: 651.79, measured: 651 g / mol)

[0281]

[0282] [Synthesis Example 3] Synthesis of Compound A-3

[0283]

[0284] The same procedure as in Synthesis Example 1 was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1, to obtain the target compound A-3 (8.6 g, yield 64%).

[0285] Mass (theoretical: 717.83, measured: 717 g / mol)

[0286]

[0287] [Synthesis Example 4] Synthesis of Compound A-4

[0288]

[0289] The same procedure as in Synthesis Example 1 was followed, except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1, to obtain the target compound A-4 (9.1 g, yield 68%).

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

[0291]

[0292] [Synthesis Example 5] Synthesis of Compound A-5

[0293]

[0294] The same procedure as in Synthesis Example 1 was followed, except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1, to obtain the target compound A-5 (8.3 g, yield 62%).

[0295] Mass (theoretical: 717.83, measured: 717 g / mol)

[0296]

[0297] [Synthesis Example 6] Synthesis of Compound A-6

[0298]

[0299] Except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used 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%).

[0300] Mass (theoretical: 793.93, measured: 793 g / mol)

[0301]

[0302] [Synthesis Example 7] Synthesis of Compound A-7

[0303]

[0304] Except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1, the same procedure as Synthesis Example 1 was performed to obtain the target compound A-7 (8.9 g, yield 60%).

[0305] Mass (theoretical: 793.93, measured: 793 g / mol)

[0306]

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

[0308]

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

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

[0311]

[0312] [Synthesis Example 9] Synthesis of Compound B-1

[0313]

[0314] Under a nitrogen stream, compound DDB-2 (10.0 g, 18.6 mmol) obtained in Preparation Example 2, 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) were mixed and stirred at 120°C for 4 hours.

[0315] After the reaction was completed, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane:EA = 4:1 (v / v)) to obtain the target compound B-1 (7.8 g, yield 65%).

[0316] Mass (theoretical: 641.73, measured: 641 g / mol)

[0317]

[0318] [Synthesis Example 10] Synthesis of Compound B-2

[0319]

[0320] The same procedure as in Synthesis Example 9 was followed, except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.2 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 9, to obtain the target compound B-2 (7.8 g, yield 64%).

[0321] Mass (theoretical: 651.79, measured: 651 g / mol)

[0322]

[0323] [Synthesis Example 11] Synthesis of Compound B-3

[0324]

[0325] The same procedure as in Synthesis Example 9 was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 9, to obtain the target compound B-3 (8.8 g, yield 66%).

[0326] Mass (theoretical: 717.83, measured: 717 g / mol)

[0327]

[0328] [Synthesis Example 12] Synthesis of Compound B-4

[0329]

[0330] The same procedure as in Synthesis Example 9 was followed, except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 9, to obtain the target compound B-4 (8.4 g, yield 63%).

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

[0332]

[0333] [Synthesis Example 13] Synthesis of Compound B-5

[0334]

[0335] The same procedure as in Synthesis Example 9 was followed, except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 9, to obtain the target compound B-5 (8.6 g, yield 64%).

[0336] Mass (theoretical: 717.83, measured: 717 g / mol)

[0337]

[0338] [Synthesis Example 14] Synthesis of Compound B-6

[0339]

[0340] Except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used 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%).

[0341] Mass (theoretical: 793.93, measured: 793 g / mol)

[0342]

[0343] [Synthesis Example 15] Synthesis of Compound B-7

[0344]

[0345] Except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used 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%).

[0346] Mass (theoretical: 793.93, measured: 793 g / mol)

[0347]

[0348] [Synthesis Example 16] Synthesis of Compound B-8

[0349]

[0350] The same procedure as in Synthesis Example 9 was followed, except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 9, to obtain the target compound B-8 (9.5 g, yield 64%).

[0351] Mass (theoretical: 793.93, measured: 793 g / mol)

[0352]

[0353] [Synthesis Example 17] Synthesis of Compound C-1

[0354]

[0355] Under a nitrogen stream, compound DDB-3 (10.0 g, 16.3 mmol) obtained in Preparation Example 3, 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) were mixed and stirred at 120°C for 4 hours.

[0356] After the reaction was completed, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane:EA = 4:1 (v / v)) to obtain the target compound C-1 (7.6 g, yield 65%).

[0357] Mass (theoretical: 717.83, measured: 717 g / mol)

[0358]

[0359] [Synthesis Example 18] Synthesis of Compound C-2

[0360]

[0361] The same procedure as in Synthesis Example 17 was followed, except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.4 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 17, to obtain the target compound C-2 (7.8 g, yield 64%).

[0362] Mass (theoretical: 727.89, measured: 727 g / mol)

[0363]

[0364] [Synthesis Example 19] Synthesis of Compound C-3

[0365]

[0366] Except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used 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%).

[0367] Mass (theoretical: 793.93, measured: 793 g / mol)

[0368]

[0369] [Synthesis Example 20] Synthesis of Compound C-4

[0370]

[0371] Except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used 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%).

[0372] Mass (theoretical: 793.93, measured: 793 g / mol)

[0373]

[0374] [Synthesis Example 21] Synthesis of Compound C-5

[0375]

[0376] Except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used 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%).

[0377] Mass (theoretical: 793.93, measured: 793 g / mol)

[0378]

[0379] [Synthesis Example 22] Synthesis of Compound C-6

[0380]

[0381] Except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (8.2 g, 19.6 mmol) was used 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%).

[0382] Mass (theoretical: 870.02, measured: 870 g / mol)

[0383]

[0384] [Synthesis Example 23] Synthesis of Compound C-7

[0385]

[0386] Except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (8.2 g, 19.6 mmol) was used 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%).

[0387] Mass (theoretical: 870.02, measured: 870 g / mol)

[0388]

[0389] [Synthesis Example 24] Synthesis of Compound C-8

[0390]

[0391] Except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (8.2 g, 19.6 mmol) was used 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%).

[0392] Mass (theoretical: 870.02, measured: 870 g / mol)

[0393]

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

[0395]

[0396] Under a nitrogen stream, compound DDB-4 (10.0 g, 18.1 mmol) obtained in Preparation Example 4, 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.

[0397] After the reaction was completed, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane:EA = 4:1 (v / v)) to obtain the target compound D-1 (8.1 g, yield 68%).

[0398] Mass (theoretical: 658.83, measured: 658 g / mol)

[0399]

[0400] [Synthesis Example 26] Synthesis of Compound D-2

[0401]

[0402] The same procedure as in Synthesis Example 25 was followed, except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.0 g, 21.7 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 25, to obtain the target compound D-2 (8.1 g, yield 67%).

[0403] Mass (theoretical: 668.89, measured: 668 g / mol)

[0404]

[0405] [Synthesis Example 27] Synthesis of Compound D-3

[0406]

[0407] Except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) was used 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%).

[0408] Mass (theoretical: 734.93, measured: 734 g / mol)

[0409]

[0410] [Synthesis Example 28] Synthesis of Compound D-4

[0411]

[0412] Except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) was used 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%).

[0413] Mass (theoretical: 734.93, measured: 734 g / mol)

[0414]

[0415] [Synthesis Example 29] Synthesis of Compound D-5

[0416]

[0417] Except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) was used 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%).

[0418] Mass (theoretical: 734.93, measured: 734 g / mol)

[0419]

[0420] [Synthesis Example 30] Synthesis of Compound D-6

[0421]

[0422] Except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.1 g, 21.7 mmol) was used 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%).

[0423] Mass (theoretical: 811.03, measured: 811 g / mol)

[0424]

[0425] [Synthesis Example 31] Synthesis of Compound D-7

[0426]

[0427] Except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (9.1 g, 21.7 mmol) was used 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%).

[0428] Mass (theoretical: 811.03, measured: 811 g / mol)

[0429]

[0430] [Synthesis Example 32] Synthesis of Compound D-8

[0431]

[0432] Except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.1 g, 21.7 mmol) was used 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%).

[0433] Mass (theoretical: 811.03, measured: 811 g / mol)

[0434]

[0435] [Synthesis Example 33] Synthesis of Compound E-1

[0436]

[0437] Under a nitrogen stream, compound DDB-5 (10.0 g, 18.1 mmol) obtained in Preparation Example 5, 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.

[0438] After the reaction was completed, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane:EA = 4:1 (v / v)) to obtain the target compound E-1 (7.6 g, yield 64%).

[0439] Mass (theoretical: 658.83, measured: 658 g / mol)

[0440]

[0441] [Synthesis Example 34] Synthesis of Compound E-2

[0442]

[0443] The same procedure as in Synthesis Example 33 was followed, except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.0 g, 21.7 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 33, to obtain the target compound E-2 (8.0 g, yield 66%).

[0444] Mass (theoretical: 668.89, measured: 668 g / mol)

[0445]

[0446] [Synthesis Example 35] Synthesis of Compound E-3

[0447]

[0448] Except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) was used 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%).

[0449] Mass (theoretical: 734.93, measured: 734 g / mol)

[0450]

[0451] [Synthesis Example 36] Synthesis of Compound E-4

[0452]

[0453] Except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) was used 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%).

[0454] Mass (theoretical: 734.93, measured: 734 g / mol)

[0455]

[0456] [Synthesis Example 37] Synthesis of Compound E-5

[0457]

[0458] Except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) was used 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%).

[0459] Mass (theoretical: 734.93, measured: 734 g / mol)

[0460]

[0461] [Synthesis Example 38] Synthesis of Compound E-6

[0462]

[0463] Except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.1 g, 21.7 mmol) was used 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%).

[0464] Mass (theoretical: 811.03, measured: 811 g / mol)

[0465]

[0466] [Synthesis Example 39] Synthesis of Compound E-7

[0467]

[0468] Except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (9.1 g, 21.7 mmol) was used 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%).

[0469] Mass (theoretical: 811.03, measured: 811 g / mol)

[0470]

[0471] [Synthesis Example 40] Synthesis of Compound E-8

[0472]

[0473] Except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.1 g, 21.7 mmol) was used 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%).

[0474] Mass (theoretical: 811.03, measured: 811 g / mol)

[0475]

[0476] [Preparation Example 6] Synthesis of compound Cz-D1

[0477]

[0478] Under a nitrogen stream, 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7 (134.3 g, 530.6 mmol), Iodobenzene (130.0 g, 636.7 mmol), Cu (16.8 g, 265.3 mmol), K2CO3 (146.7 g, 1,061.3 mmol) and toluene (1000 ml) were mixed and stirred at 110°C for 12 hours.

[0479] After the reaction was completed, the organic layer was extracted with ethyl acetate, moisture was removed with MgSO4, and the residue was purified by column chromatography (Hexane:EA = 5:1 (v / v)) to obtain Cz-D1 (125.7 g, yield 72%).

[0480] Mass (theoretical: 329.25, measured: 329 g / mol)

[0481]

[0482] [Preparation Example 7] Synthesis of compound Cz-D2

[0483]

[0484] The same procedure as in Preparation Example 6 was followed, except that 4-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of the iodobenzene used in Preparation Example 6, to obtain the target compound Cz-D2 (135.5 g, yield 63%).

[0485] Mass (theoretical: 405.35, measured: 405 g / mol)

[0486]

[0487] [Preparation Example 8] Synthesis of compound Cz-D3

[0488]

[0489] The same procedure as in Preparation Example 6 was followed, except that 3-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of the iodobenzene used in Preparation Example 6, to obtain the target compound Cz-D3 (148.4 g, yield 69%).

[0490] Mass (theoretical: 405.35, measured: 405 g / mol)

[0491]

[0492] [Preparation Example 9] Synthesis of compound Cz-D4

[0493]

[0494] The same procedure as in Preparation Example 6 was followed, except that 2-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of the iodobenzene used in Preparation Example 6, to obtain the target compound Cz-D4 (96.8 g, yield 45%).

[0495] Mass (theoretical: 405.35, measured: 405 g / mol)

[0496]

[0497] [Preparation Example 10] Synthesis of compound BCz-D1

[0498] <Step 1> Synthesis of 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7

[0499]

[0500] 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'-bi(1,3,2-dioxaborolane) (84.8 g, 334.1 mmol), Pd(dppf)Cl2 (26.6 g, 30.3 mmol), KOAc (85.8 g, 911.1 mmol) and 1,4-Dioxane (1000 ml) were mixed and stirred at 130°C for 12 hours.

[0501] After the reaction was completed, the organic?? was extracted with ethyl acetate, moisture was removed with MgSO4, and the residue 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-dioxaborolan-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7 (96.0 g, yield 84%).

[0502] Mass (theoretical: 376.3, measured: 376 g / mol)

[0503] <Step 2> Synthesis of compound BCz-D1

[0504]

[0505] Under a nitrogen stream, 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7 (96.0 g, 255.1 mmol), 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7 (77.5 g, 306.1 mmol), Pd(PPh3)4 (14.7 g, 12.7 mmol), K2CO3 (88.1 g, 637.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0506] After the reaction was completed, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:EA = 7:1 (v / v)) to obtain the target compound BCz-D1 (71.1 g, yield 66%).

[0507] Mass (theoretical: 422.59, measured: 422 g / mol)

[0508]

[0509] [Preparation Example 11] Synthesis of compound BCz-D2

[0510] <Step 1>

[0511]

[0512] The target compound was obtained by performing the same process as in step 1 of preparation example 10, except that compound Cz-D2 (100 g, 246.7 mmol) obtained in preparation example 7 was used instead of compound Cz-D1 used in step 1 of preparation example 10.

[0513] Step 2

[0514]

[0515] Except that 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-dioxaborolan-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7 used in step 2 of preparation example 10, the same process as step 2 of preparation example 10 was performed to obtain the target compound BCz-D2 (66.4 g, final yield 54.0%).

[0516] Mass (theoretical: 498.69, measured: 498 g / mol)

[0517]

[0518] [Preparation Example 12] Synthesis of compound BCz-D3

[0519] <Step 1>

[0520]

[0521] The target compound was obtained by performing the same procedure as in step 1 of preparation example 10, except that compound Cz-D3 (100 g, 246.7 mmol) obtained in preparation example 8 was used instead of compound Cz-D1 used in step 1 of preparation example 10.

[0522] Step 2

[0523]

[0524] Except that 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-dioxaborolan-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7 used in step 2 of preparation example 10, the same process as step 2 of preparation example 10 was performed to obtain the target compound BCz-D3 (59.7 g, final yield 48.5%).

[0525] Mass (theoretical: 498.69, measured: 498 g / mol)

[0526]

[0527] [Preparation Example 13] Synthesis of compound BCz-D4

[0528] <Step 1>

[0529]

[0530] The target compound was obtained by performing the same process as in step 1 of preparation example 10, except that compound Cz-D4 (100 g, 246.7 mmol) obtained in preparation example 9 was used instead of Cz-D1 used in step 1 of preparation example 10.

[0531] Step 2

[0532]

[0533] Except that 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-dioxaborolan-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7 used in step 2 of Preparation Example 10, the same process as step 2 of Preparation Example 10 was performed to obtain the target compound BCz-D4 (59.4 g, final yield 48.3%).

[0534] Mass (theoretical: 498.69, measured: 498 g / mol)

[0535]

[0536] [Synthesis Example 41] Synthesis of Compound F-1

[0537]

[0538] Under a nitrogen stream, 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 completed, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain the target compound F-1 (13.0 g, yield 82%).

[0539] Mass (theoretical: 670.93, measured: 670 g / mol)

[0540]

[0541] [Synthesis Example 42] Synthesis of Compound F-2

[0542]

[0543] The same procedure as in Synthesis Example 41 was followed, except that compound Cz-D2 (11.4 g, 28.3 mmol) obtained in Preparation Example 7 was used instead of compound Cz-D1 used in Synthesis Example 41, to obtain the target compound F-2 (13.8 g, yield 78%).

[0544] Mass (theoretical: 747.02, measured: 747 g / mol)

[0545]

[0546] [Synthesis Example 43] Synthesis of Compound F-3

[0547]

[0548] The same procedure as in Synthesis Example 41 was followed, except that compound Cz-D3 (11.4 g, 28.3 mmol) obtained in Preparation Example 8 was used instead of compound Cz-D1 used in Synthesis Example 41, to obtain the target compound F-3 (13.2 g, yield 75%).

[0549] Mass (theoretical: 747.02, measured: 747 g / mol)

[0550]

[0551] [Synthesis Example 44] Synthesis of Compound F-4

[0552]

[0553] The same procedure as in Synthesis Example 41 was followed, except that compound Cz-D4 (11.4 g, 28.3 mmol) obtained in Preparation Example 9 was used instead of compound Cz-D1 used in Synthesis Example 41, to obtain the target compound F-4 (12.2 g, yield 69%).

[0554] Mass (theoretical: 747.02, measured: 747 g / mol)

[0555]

[0556] [Synthesis Example 45] Synthesis of Compound F-5

[0557]

[0558] Under a nitrogen stream, 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 completed, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain the target compound F-5 (10.2 g, yield 62%).

[0559] Mass (theoretical: 747.02, measured: 747 g / mol)

[0560]

[0561] [Synthesis Example 46] Synthesis of Compound F-6

[0562]

[0563] Under a nitrogen stream, 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 completed, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain the target compound F-6 (9.4 g, yield 63%).

[0564] Mass (theoretical: 747.02, measured: 747 g / mol)

[0565]

[0566] [Synthesis Example 47] Synthesis of Compound F-7

[0567]

[0568] Under a nitrogen stream, 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 completion of the reaction, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain the target compound F-7 (8.1 g, yield 54%).

[0569] Mass (theoretical: 747.02, measured: 747 g / mol)

[0570]

[0571] [Synthesis Example 48] Synthesis of Compound F-8

[0572]

[0573] The same procedure as in Synthesis Example 41 was followed, except that 4-bromo-1,1'-biphenyl (6.6 g, 28.3 mmol) was used instead of the compound Cz-D1 used in Synthesis Example 41, to obtain the target compound F-8 (9.9 g, yield 73%).

[0574] Mass (theoretical: 574.79, measured: 574 g / mol)

[0575]

[0576] [Synthesis Example 49] Synthesis of Compound F-9

[0577]

[0578] The same procedure as in Synthesis Example 45 was followed, except that 4-bromo-1,1'-biphenyl (5.6 g, 24.1 mmol) was used instead of the compound Cz-D1 used in Synthesis Example 45, to obtain the target compound F-9 (10.2 g, yield 78%).

[0579] Mass (theoretical: 650.88, measured: 650 g / mol)

[0580]

[0581] [Synthesis Example 50] Synthesis of Compound F-10

[0582]

[0583] The same procedure as in Synthesis Example 46 was followed, except that 4-bromo-1,1'-biphenyl (5.6 g, 24.1 mmol) was used instead of the compound Cz-D1 used in Synthesis Example 46, to obtain the target compound F-10 (9.8 g, yield 75%).

[0584] Mass (theoretical: 650.88, measured: 650 g / mol)

[0585]

[0586] [Example 1] Fabrication of a green organic EL device

[0587] Compound A-1 synthesized in Synthesis Example 1 and compound E-1 synthesized in Synthesis Example 41 were purified by high-purity sublimation using a commonly known method, and then a green organic EL device was manufactured according to the following process.

[0588] First, a glass substrate coated with a 1500 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then transferred to a UV OZONE cleaner (Power Sonic 405, Hwasin Tech). The substrate was then cleaned for 5 minutes using UV and transferred to a vacuum deposition machine.

[0589] On the prepared ITO transparent electrode, an organic EL device was fabricated by stacking HT + 2% PA (100 Å) / HT (1200 Å) / HA (300 Å) / 30% compound F-1 + 60% compound A-1 + 10% Ir(ppy)3(400 Å) / EA (50 Å) / ET + LiQ (300 Å_1:1) / LiF (10 Å) / Al (1000 Å) in that order. At this time, the structures of HT, HA, PA, Ir(ppy)3, EA, and ET used are as follows, respectively.

[0590]

[0591]

[0592] [Example 2] ~ [Example 400] - Manufacture of green organic EL device

[0593] A green organic EL device was manufactured in the same manner as in Example 1, except that Compounds F-2 to F-10, each synthesized in Synthesis Examples 42 to 50, were used instead of Compound F-1, which was used as a luminescent host material in forming the luminescent layer in Example 1, and Compounds A-2 to E-8, each synthesized in Synthesis Examples 2 to 40, were used instead of Compound A-1 (see Table 1).

[0594]

[0595] [Comparative Example 1] Fabrication of a Green Organic EL Device

[0596] A green organic EL device was manufactured using the same process as in Example 1, except that the following compound HT-1 was used instead of the following compound F-1 as a light-emitting host material when forming the light-emitting layer in Example 1, and the following compound ET-1 was used instead of the following compound A-1. The structures of HT-1 and ET-1 used here are as follows, respectively.

[0597]

[0598]

[0599] [Evaluation Example 1]

[0600] For the green organic EL devices manufactured in Examples 1 to 400 and Comparative Example 1, the driving voltage, current efficiency, luminescence peak, and lifespan at a current density of 10 mA / cm2 were measured, and the results are shown in Table 1 below.

[0601] Sample Host 1 Host 2 Driving Voltage (V) EL Peak (nm) Current Efficiency (cd / A) Lifespan (hr, T97) Example 1A-1F-13.8951763.2382 Example 2A-1F-23.7751562.4381 Example 3A-1F-33.7151865.5384 Example 4A-1F-43.6851867.2381 Example 5A-1F-53.6651568.1388 Example 6A-1F-63.8951866.4380 Example 7A-1F-73.9851864.1384 Example 8A-1F-83.7151866.4381 Example 9A-1F-93.7551862.1381 Example 10A-1F-103.6551763.4377 Example 11A-2F-13.7451564.3374 Example 12A-2F-23.6651867.8372 Example 13A-2F-33.6151865.1371 Example 14A-2F-43.6451768.1379 Example 15A-2F-53.8451566.4372 Example 16A-2F-63.6751864.1373 Example 17A-2F-73.6851866.4382 Example 18A-2F-83.6451862.1389 Example 19A-2F-93.8451763.4382 Example 20A-2F-103.6751564.3381 Example 21A-3F-13.6851867.8384 Example 22A-3F-23.7151865.1381 Example 23A-3F-33.6651563.4388 Example 24A-3F-43.9151864.4380 Example 25A-3F-53.9251862.2384 Example 26A-3F-63.9151862.8381 Example 27A-3F-73.8251765.3381 Example 28A-3F-83.8851566.3384 Example 29A-3F-93.8251563.1386 Example 30A-3F-103.7451861.9381 Example 31A-4F-13.7451862.7384 Example 32A-4F-23.6551765.3392 Example 33A-4F-33.7551562.4394 Example 34A-4F-43.8951863.4373 Example 35A-4F-53.7751564.2382 Example 36A-4F-63.7151464.3389 Example 37A-4F-73.6851563.2382 Example 38A-4F-83.6651866.3381 Example 39A-4F-93.8951964.2384 Example 40A-4F-103.9851163.4381 Example 41A-5F-13.7151561.2388 Example 42A-5F-23.7552062.1391 Example 43A-5F-33.6551163.4392 Example 44A-5F-43.7451464.3391 Example 45A-5F-53.5151567.8390 Example 46A-5F-63.5251565.1393 Example 47A-5F-73.5551863.4384 Example 48A-5F-83.5351364.4399 Example 49A-5F-93.5251862.2393 Example 50A-5F-103.5151562.8391 Example 51A-6F-13.5751865.3401 Example 52A-6F-23.5851866.3400 Example 53A-6F-33.7151763.1403 Example 54A-6F-43.6651561.9392 Example 55A-6F-53.9151562.7394 Example 56A-6F-63.6751865.3373 Example 57A-6F-73.6851860.4382 Example 58A-6F-83.7151162.3389 Example 59A-6F-93.6651466.5382 Example 60A-6F-103.9151563.2381 Example 61A-7F-13.9851562.4384 Example 62A-7F-23.7151865.5381 Example 63A-7F-33.7551167.2388 Example 64A-7F-43.5151468.1391 Example 65A-7F-53.5251568.3392 Example 66A-7F-63.5551568.3391 Example 67A-7F-73.5351868.7390 Example 68A-7F-83.5251368.3393 Example 69A-7F-93.5151868.2392 Example 70A-7F-103.5751568.1392 Example 71A-8F-13.5851868.2390 Example 72A-8F-23.7151765.1384 Example 73A-8F-33.6651763.4381 Example 74A-8F-43.9151564.4371 Example 75A-8F-53.6751862.2381 Example 76A-8F-63.6851762.8384 Example 77A-8F-73.7151865.3386 Example 78A-8F-83.6651766.3381 Example 79A-8F-93.9151563.1384 Example 80A-8F-103.9251361.9384 Example 81B-1F-13.9151462.7381 Example 82B-1F-23.8251565.3371 Example 83B-1F-33.8851662.4379 Example 84B-1F-43.8251163.4378 Example 85B-1F-53.7451364.2372 Example 86B-1F-63.7451864.3373 Example 87B-1F-73.6551563.2377 Example 88B-1F-83.7551866.3376 Example 89B-1F-93.8951864.2375 Example 90B-1F-103.7751763.4379 Example 91B-2F-13.7151561.2381 Example 92B-2F-23.6851560.4374 Example 93B-2F-33.8951862.3385 Example 94B-2F-43.7751166.5380 Example 95B-2F-53.7151463.2384 Example 96B-2F-63.6851562.4382 Example 97B-2F-73.6651565.5385 Example 98B-2F-83.8951867.8377 Example 99B-2F-93.9851365.1374 Example 100B-2F-103.6851863.4372 Example 101B-3F-13.7151164.4371 Example 102B-3F-23.6651462.2379 Example 103B-3F-33.9151562.8372 Example 104B-3F-43.9251565.3373 Example 105B-3F-53.9151866.3382 Example 106B-3F-63.8251363.1389 Example 107B-3F-73.8851861.9382 Example 108B-3F-83.8251562.7381 Example 109B-3F-93.7451865.3384 Example 110B-3F-103.7451762.4381 Example 111B-4F-13.6551763.4374 Example 112B-4F-23.7751564.2372 Example 113B-4F-33.7151864.3371 Example 114B-4F-43.6851763.2379 Example 115B-4F-53.6651866.3372 Example 116B-4F-63.8951764.2373 Example 117B-4F-73.6651563.4382 Example 118B-4F-83.6151363.2389 Example 119B-4F-93.8451462.4382 Example 120B-4F-103.6551565.5381 Example 121B-5F-13.7451667.2384 Example 122B-5F-23.6551168.1381 Example 123B-5F-33.7551566.4388 Example 124B-5F-43.8952064.1380 Example 125B-5F-53.7751163.2384 Example 126B-5F-63.7151466.3381 Example 127B-5F-73.6851564.2381 Example 128B-5F-83.6651563.4384 Example 129B-5F-93.8951861.2386 Example 130B-5F-103.9851360.4381 Example 131B-6F-13.6651862.3384 Example 132B-6F-23.8951566.5384 Example 133B-6F-33.9851863.2381 Example 134B-6F-43.7151862.4371 Example 135B-6F-53.7551765.5381 Example 136B-6F-63.6551567.2384 Example 137B-6F-73.7451568.1386 Example 138B-6F-83.9851866.4381 Example 139B-6F-93.7151164.1384 Example 140B-6F-103.7551466.4384 Example 141B-7F-13.6551562.1381 Example 142B-7F-23.7451563.4389 Example 143B-7F-33.9851864.3382 Example 144B-7F-43.3551769.3382 Example 145B-7F-53.3851769.2381 Example 146B-7F-63.3851570.1384 Example 147B-7F-73.3651870.2381 Example 148B-7F-83.3451769.9388 Example 149B-7F-93.4151869.8380 Example 150B-7F-103.3151769.5384 Example 151B-8F-13.3651569.6381 Example 152B-8F-23.3951369.4381 Example 153B-8F-33.3851470.1377 Example 154B-8F-43.3751569.4374 Example 155B-8F-53.3651669.3372 Example 156B-8F-63.3651169.3371 Example 157B-8F-73.3451569.1379 Example 158B-8F-83.3252069.4372 Example 159B-8F-93.3751169.2373 Example 160B-8F-103.7751163.2382 Example 161C-1F-13.7151466.3389 Example 162C-1F-23.6851564.2382 Example 163C-1F-33.6651563.4381 Example 164C-1F-43.8951861.2384 Example 165C-1F-53.9851360.4381 Example 166C-1F-63.6651862.3384 Example 167C-1F-73.8951566.5384 Example 168C-1F-83.9851863.2381 Example 169C-1F-93.7151862.4381 Example 170C-1F-103.7551765.5384 Example 171C-2F-13.6551567.2386 Example 172C-2F-23.7451568.1381 Example 173C-2F-33.9851866.4384 Example 174C-2F-43.7151164.1384 Example 175C-2F-53.7551466.4381 Example 176C-2F-63.6551562.1371 Example 177C-2F-73.7451563.4384 Example 178C-2F-83.9851864.3386 Example 179C-2F-93.3551769.3381 Example 180C-2F-103.3851769.2384 Example 181C-3F-13.3851570.1384 Example 182C-3F-23.9851864.3381 Example 183C-3F-33.3551769.3389 Example 184C-3F-43.3851769.2382 Example 185C-3F-53.3851570.1382 Example 186C-3F-63.3651870.2381 Example 187C-3F-73.3451769.9384 Example 188C-3F-83.4151869.8381 Example 189C-3F-93.3151769.5388 Example 190C-3F-103.3651569.6372 Example 191C-4F-13.3951369.4371 Example 192C-4F-23.3851470.1379 Example 193C-4F-33.3751569.4372 Example 194C-4F-43.3651669.3373 Example 195C-4F-53.3651169.3382 Example 196C-4F-63.3451569.1389 Example 197C-4F-73.3252069.4382 Example 198C-4F-83.3751169.2381 Example 199C-4F-93.7751163.2384 Example 200C-4F-103.7151466.3381 Example 201C-5F-13.6851564.2381 Example 202C-5F-23.6651563.4384 Example 203C-5F-33.8951861.2386 Example 204C-5F-43.9851360.4381 Example 205C-5F-53.6651862.3384 Example 206C-5F-63.8951566.5384 Example 207C-5F-73.9851863.2381 Example 208C-5F-83.7151862.4371 Example 209C-5F-93.6551567.2384 Example 210C-5F-103.7451568.1386 Example 211C-6F-13.9851866.4381 Example 212C-6F-23.7151164.1384 Example 213C-6F-33.7551466.4384 Example 214C-6F-43.6551562.1381 Example 215C-6F-53.7451563.4389 Example 216C-6F-63.9851864.3382 Example 217C-6F-73.3551769.3382 Example 218C-6F-83.3851769.2381 Example 219C-6F-93.3851570.1384 Example 220C-6F-103.9851864.3381 Example 221C-7F-13.3551769.3388 Example 222C-7F-23.3851769.2380 Example 223C-7F-3 3.385 1570.1384 Example 224C-7F-4 3.365 1870.2381 Example 225C-7F-5 3.345 1769.9381 Example 226C-7F-6 3.415 1869.8377 Example 227C-7F-7 3.315 1769.5374 Example 228C-7F-8 3.365 1569.6372 Example 229C-7F-9 3.395 1369.4371 Example 230C-7F-10 3.385 1470.1379 Example 231C-8F-13.3451769.9372 Example 232C-8F-23.4151869.8373 Example 233C-8F-33.3151769.5382 Example 234C-8F-43.3651569.6389 Example 235C-8F-53.3951369.4382 Example 236C-8F-63.3851470.1381 Example 237C-8F-73.3751569.4384 Example 238C-8F-83.3651669.3382 Example 239C-8F-93.3651169.3381 Example 240C-8F-103.3451569.1384 Example 241D-1F-13.3252069.4381 Example 242D-1F-23.3751169.2388 Example 243D-1F-33.7751163.2380 Example 244D-1F-43.7151466.3384 Example 245D-1F-53.6851564.2381 Example 246D-1F-63.6651563.4381 Example 247D-1F-73.8951861.2377 Example 248D-1F-83.9851360.4374 Example 249D-1F-93.6651862.3372 Example 250D-1F-103.8951566.5371 Example 251D-2F-13.9851863.2379 Example 252D-2F-23.7151862.4381 Example 253D-2F-33.6551567.2381 Example 254D-2F-43.7451568.1377 Example 255D-2F-53.9851866.4374 Example 256D-2F-63.7151164.1372 Example 257D-2F-73.7551466.4371 Example 258D-2F-83.6551562.1379 Example 259D-2F-93.3651870.2372 Example 260D-2F-103.3451769.9373 Example 261D-3F-13.4151869.8382 Example 262D-3F-23.3151769.5389 Example 263D-3F-33.3651569.6382 Example 264D-3F-43.3951369.4381 Example 265D-3F-53.3851470.1384 Example 266D-3F-63.3451769.9381 Example 267D-3F-73.4151869.8381 Example 268D-3F-83.3151769.5377 Example 269D-3F-93.3651569.6374 Example 270D-3F-103.3951369.4372 Example 271D-4F-13.3851470.1371 Example 272D-4F-23.3751569.4379 Example 273D-4F-33.3651669.3372 Example 274D-4F-43.3651169.3373 Example 275D-4F-53.3451569.1382 Example 276D-4F-63.3252069.4389 Example 277D-4F-73.3751169.2382 Example 278D-4F-83.7751163.2381 Example 279D-4F-93.3851466.3384 Example 280D-4F-103.3651564.2381 Example 281D-5F-13.3451460.4389 Example 282D-5F-23.4151562.3382 Example 283D-5F-33.3151566.5382 Example 284D-5F-43.3651863.2381 Example 285D-5F-53.3951762.4384 Example 286D-5F-63.3851765.5381 Example 287D-5F-73.3451567.2388 Example 288D-5F-83.4151868.1380 Example 289D-5F-93.3151766.4384 Example 290D-5F-103.3651764.1381 Example 291D-6F-13.3951566.4381 Example 292D-6F-23.3851862.1377 Example 293D-6F-33.3751763.4374 Example 294D-6F-43.3651864.3372 Example 295D-6F-53.3651769.3371 Example 296D-6F-63.3451569.2379 Example 297D-6F-73.3251370.1372 Example 298D-6F-83.3751464.3373 Example 299D-6F-93.7751769.3382 Example 300D-6F-103.7151869.2389 Example 301D-7F-13.6851770.1382 Example 302D-7F-23.6651570.2381 Example 303D-7F-33.8951369.9384 Example 304D-7F-43.9851469.8382 Example 305D-7F-53.6651569.5381 Example 306D-7F-63.8951669.6384 Example 307D-7F-73.7151169.4381 Example 308D-7F-83.6851570.1388 Example 309D-7F-93.6652069.4380 Example 310D-7F-103.8951169.3384 Example 311D-8F-13.9851169.3381 Example 312D-8F-23.6651469.1381 Example 313D-8F-33.8951569.4377 Example 314D-8F-43.9851569.2374 Example 315D-8F-53.7151863.2372 Example 316D-8F-63.6551366.3371 Example 317D-8F-73.7451864.2379 Example 318D-8F-83.9851563.4381 Example 319D-8F-93.7151861.2381 Example 320D-8F-103.7551860.4377 Example 321E-1F-13.6551562.3374 Example 322E-1F-23.3651566.5372 Example 323E-1F-33.3451763.2371 Example 324E-1F-43.4151862.4379 Example 325E-1F-53.3151767.2372 Example 326E-1F-63.3651568.1373 Example 327E-1F-73.3951366.4382 Example 328E-1F-83.3851464.1389 Example 329E-1F-93.3451566.4374 Example 330E-1F-103.4151662.1372 Example 331E-2F-13.3151163.4371 Example 332E-2F-23.3651564.3379 Example 333E-2F-33.3952069.3372 Example 334E-2F-43.3851169.2373 Example 335E-2F-53.3751170.1382 Example 336E-2F-63.3651464.3389 Example 337E-2F-73.3651569.3382 Example 338E-2F-83.3451469.2381 Example 339E-2F-93.3251570.1384 Example 340E-2F-103.3751570.2381 Example 341E-3F-13.7751869.9389 Example 342E-3F-23.3851769.8382 Example 343E-3F-33.3651769.5382 Example 344E-3F-43.3451569.6381 Example 345E-3F-53.4151869.4384 Example 346E-3F-63.3151770.1381 Example 347E-3F-73.3651769.9388 Example 348E-3F-83.3951569.8380 Example 349E-3F-93.3851869.5384 Example 350E-3F-103.3451769.6381 Example 351E-4F-13.4151869.4381 Example 352E-4F-23.3151770.1377 Example 353E-4F-33.3651569.9374 Example 354E-4F-43.3951369.8372 Example 355E-4F-53.3851469.5371 Example 356E-4F-63.3751769.6379 Example 357E-4F-73.3651869.4372 Example 358E-4F-83.3651770.1373 Example 359E-4F-93.3451569.4382 Example 360E-4F-103.3251369.3389 Example 361E-5F-13.3751469.3382 Example 362E-5F-23.7751569.1381 Example 363E-5F-33.7151669.4384 Example 364E-5F-43.4151169.2382 Example 365E-5F-53.3151563.2381 Example 366E-5F-63.3652066.3384 Example 367E-5F-73.3951164.2381 Example 368E-5F-83.3851160.4388 Example 369E-5F-93.3451462.3380 Example 370E-5F-103.4151566.5384 Example 371E-6F-13.3151563.2381 Example 372E-6F-23.3651862.4381 Example 373E-6F-33.3951365.5377 Example 374E-6F-43.3851867.2374 Example 375E-6F-53.3751568.1372 Example 376E-6F-63.3651866.4371 Example 377E-6F-73.3651764.1379 Example 378E-6F-83.3451866.4381 Example 379E-6F-93.3251762.1381 Example 380E-6F-103.3751563.4377 Example 381E-7F-13.7751364.3374 Example 382E-7F-23.7151469.1372 Example 383E-7F-33.6851769.4371 Example 384E-7F-43.6651869.2379 Example 385E-7F-53.8951763.2372 Example 386E-7F-63.9851566.3373 Example 387E-7F-73.6651364.2382 Example 388E-7F-83.8951460.4389 Example 389E-7F-93.7151562.3382 Example 390E-7F-103.6851666.5381 Example 391E-8F-13.6651163.2384 Example 392E-8F-23.8951562.4381 Example 393E-8F-33.9852065.5381 Example 394E-8F-43.6651167.2377 Example 395E-8F-53.8951168.1374Example 396E-8F-63.9851466.4372Example 397E-8F-73.7151564.1371Example 398E-8F-83.6551566.4379Example 399E-8F-93.7451862.1372Example 400E-8F-103.9851363.4373Comparative Example 1HT-1ET-15.0151444.3285.

[0602]

[0603] As shown in Table 1 above, the green organic EL device of Example 1-400, in which compounds A-1 to E-8 according to the present invention were mixed with compounds F-1 to F-10 and used as a light-emitting layer, was found to exhibit superior performance in terms of current efficiency, driving voltage, and lifespan characteristics, compared to the green organic EL device of Comparative Example 1, in which compound ET-1 instead of compound A-1 was mixed with compound HT-1 and used as a light-emitting layer. This is because the unshared electron pair of the heteroatom in the carbazole group of compound ET-1 is used as another movement path for holes, and thus, when excitons are formed in the light-emitting layer, losses occur in the number of holes transferred to another movement path, whereas compounds A-1 to E-8 of the present invention, which have an aryl group such as a phenyl group or a biphenyl group instead of a carbazole group, do not cause exciton loss, and the stability for injected electrons is improved due to the aryl group, thereby improving the overall characteristics of the device.

Claims

1. A composition for an organic electroluminescent device, comprising a first host represented by the following chemical formula 1 and a second host represented by the following chemical formula 2: [Chemical Formula 1] [Chemical Formula 2] (In the above 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 integers from 0 to 5, respectively, R1 to R5 are the same or different, and each independently represents deuterium (D), C1 to C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 alkynyl group of, and C6~C 40 is selected from the group consisting of aryl groups, D is deuterium, Ar1 and Ar2 are each independently C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40 Aryl group of, heteroaryl group having 5 to 40 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 40 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 40 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 40 Aryl boron group, C6~C 40 Arylphosphine group, C6~C 40 Arylphosphine oxide group and C6~C 40 Selected from the group consisting of arylamine groups, The alkyl group, alkenyl group, alkynyl group and aryl group of the above R1 to R5 are each independently deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of C6~C 40 Aryl group of C1~C 40 Alkyloxy group, C6~C 40 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 40 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 40 Aryl boron group, C6~C 40 Arylphosphine group, C6~C 40 Arylphosphine oxide group and C6~C 40 is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other, The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of the above Ar1 and Ar2 are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40 Aryl group of , heteroaryl group having 5 to 40 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 40 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 40 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 40 Aryl boron group, C6~C 40 Arylphosphine group, C6~C 40 Arylphosphine oxide group and C6~C 40 (Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other).

2. In paragraph 1, R1 is C6~C 40 is an aryl group, R4 and R5 are hydrogen, deuterium, or C6~C 40 is an aryl group, The aryl groups of R1, R4 and R5 above are each independently deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group, and C6~C 40 A composition for an organic electroluminescent device, which is substituted or unsubstituted with one or more substituents selected from the group consisting of aryl groups, and in this case, when there are multiple substituents, they are the same or different from each other.

3. In paragraph 1, The above first host is a composition for an organic electroluminescent device, which is a compound represented by the following chemical formula 3 or 4: [Chemical Formula 3] [Chemical Formula 4] (In the above chemical formulas 3 and 4, R2 to R5, b, c, d and e are each as defined in paragraph 1, R 11 Silver C6~C 40 is an aryl group, f is an integer from 0 to 3, R 12 is hydrogen, deuterium (D), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 alkynyl group of, and C6~C 40 is selected from the group consisting of aryl groups, The above R 11 Aryl group of and the above R 12 The alkyl group, alkenyl group, alkynyl group and aryl group are each independently deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40 Aryl group of , heteroaryl group having 5 to 40 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 40 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 40 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 40 Aryl boron group, C6~C 40 Arylphosphine group, C6~C 40 Arylphosphine oxide group and C6~C 40 (Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other).

4. In paragraph 3, R 11 is a substituent selected from the group consisting of the following substituents S1-1 to S1-10, R4 and R5 are the same or different from each other, and are each independently hydrogen or deuterium (D), or a substituent selected from the group consisting of the following substituents S1-1 to S1-10, A composition for an organic electroluminescent device, wherein the following substituents S1-1 to S1-10 are each independently substituted or unsubstituted with deuterium (D): .

5. In paragraph 1, A composition for an organic electroluminescent device, wherein the first host 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 above chemical formulas 5 to 8, R2 to R5, b, c, d and e are each as defined in paragraph 1, Dn means that it is replaced by n deuterium atoms (D), and 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 is deuterium (D), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 alkynyl group of, and C6~C 40 is selected from the group consisting of aryl groups, The above R 12 The alkyl group, alkenyl group, alkynyl group and aryl group are each independently deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40 Aryl group of , heteroaryl group having 5 to 40 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 40 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 40 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 40 Aryl boron group, C6~C 40 Arylphosphine group, C6~C 40 Arylphosphine oxide group and C6~C 40 (Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other).

6. In paragraph 1, A composition for an organic electroluminescent device, wherein the first host is a compound selected from the group consisting of compounds A-1 to E-8: .

7. In paragraph 1, The number of deuterium (D) contained in the above second host is at least 14, The above Ar1 and Ar2 are the same or different from each other, and are each independently C6~C 40 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 40 nuclear atoms, The aryl group and heteroaryl group of the above Ar1 and Ar2 are each independently deuterium (D), C1~C 40 Alkyl group of C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40 is substituted or unsubstituted with one or more substituents selected from the group consisting of aryl groups and heteroaryl groups having 5 to 40 nuclear atoms, and when there are multiple substituents, they are the same or different from each other, However, a composition for an organic electroluminescent device in which both the aryl group and heteroaryl group of Ar1 and Ar2 are substituted with deuterium (D) is excluded.

8. In paragraph 1, The second host is a composition for an organic electroluminescent device, which is a compound represented by the following chemical formula 9: [Chemical Formula 9] (In the above chemical formula 9, Ar1 is as defined in paragraph 1, h is 0 or 1, i is an integer from 1 to 7, D is deuterium, Ar3 is C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40 Aryl group of, heteroaryl group having 5 to 40 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 40 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 40 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 40 Aryl boron group, C6~C 40 Arylphosphine group, C6~C 40 Arylphosphine oxide group and C6~C 40 Selected from the group consisting of arylamine groups, The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of the above Ar3 are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40 Aryl group of , heteroaryl group having 5 to 40 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 40 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 40 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 40 Aryl boron group, C6~C 40 Arylphosphine group, C6~C 40 Arylphosphine oxide group and C6~C 40 (Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other).

9. In paragraph 1, The second host is a composition for an organic electroluminescent device, which is a compound represented by the following chemical formula 10: [Chemical Formula 10] (In the above chemical formula 10, Ar1 is as defined in paragraph 1, h is 0 or 1, i is an integer from 1 to 7, D is deuterium, Ar3 is C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40 Aryl group of, heteroaryl group having 5 to 40 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 40 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 40 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 40 Aryl boron group, C6~C 40 Arylphosphine group, C6~C 40 Arylphosphine oxide group and C6~C 40 Selected from the group consisting of arylamine groups, The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of the above Ar3 are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 40 Aryl group of , heteroaryl group having 5 to 40 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 40 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 40 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 40 Aryl boron group, C6~C 40 Arylphosphine group, C6~C 40 Arylphosphine oxide group and C6~C 40 (Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other).

10. In paragraph 9, A composition for an organic electroluminescent device, wherein Ar1 and Ar3 are the same or different from each other and are each independently a substituent selected from the group consisting of the following substituents S2-1 to S2-10: .

11. In paragraph 1, The second host is a composition for an organic electroluminescent device, which is a compound represented by the following chemical formula 11 or 12: [Chemical Formula 11] [Chemical Formula 12] (In the above chemical formulas 11 and 12, Ar1 is as defined in paragraph 1, j is 0 or 1).

12. In paragraph 1, The above second host is a composition for an organic electroluminescent device, wherein the compound is selected from the group consisting of compounds F-1 to F-10: .

13. In paragraph 1, A composition for an organic electroluminescent device, wherein the first host and the second host are included in a weight ratio of 99:1 to 1:

99.

14. In paragraph 1, A composition for an organic electroluminescent device, further comprising a phosphorescent dopant.

15. In paragraph 1, A composition for an organic electroluminescent device, wherein the above phosphorescent dopant is a metal complex compound containing iridium (Ir) or platinum (Pt).

16. An anode; a cathode; and at least one organic layer interposed between the anode and the cathode, An organic electroluminescent device, wherein the organic layer of one or more layers comprises a composition according to any one of claims 1 to 15.

17. In paragraph 16, The organic layer above one or more layers includes a light-emitting layer, An organic electroluminescent device, wherein the composition is included in the light-emitting layer.

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