Organic compound and organic electroluminescent device comprising same

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device using same and, more specifically, to an organic compound exhibiting excellent electron injection and transport ability and thermal stability, and an organic electroluminescent device comprising same in one or more organic material layers thereof, thereby exhibiting improved properties such as luminous efficiency, driving voltage, and lifespan.

Description

Organic compounds and organic electroluminescent devices containing the same

[0001] The present invention relates to a novel organic compound and an organic electroluminescent device comprising the same, and more particularly, to an organic compound having excellent electron injection and transport capabilities and thermal stability, and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifespan by including the same in one or more organic layers.

[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] To date, NPB, BCP, Alq3, etc., which are expressed by the following chemical formulas, 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 luminescent materials. In particular, among luminescent materials, metal complex compounds containing Ir, 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 improving 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 present invention has as its technical object the provision of a novel compound having excellent heat resistance, carrier transport ability, luminescence ability, etc., which can be used as an organic layer material of an organic electroluminescent device, specifically, as an electron transport layer, an electron transport auxiliary layer, or a luminescent layer.

[0007] In addition, another technical task of the present invention is to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, and improved lifespan, including the novel compound.

[0008] Other objects and advantages of the present invention can be more clearly explained by the detailed description of the invention and the claims below.

[0009] To achieve the above-mentioned purpose, the present invention provides a compound represented by the following chemical formula 1.

[0010]

[0011] (In the above chemical formula 1,

[0012] X1 and X2 are the same or different, and are each independently O or S,

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

[0014] p, q and r are integers from 0 to 4, respectively.

[0015] R1 to R4 are the same or different and each independently represent hydrogen, deuterium (D), halogen, cyano, nitro, amino, hydroxy, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of C1~C 40 Heterocycloalkyl group, C6~C 60 Aryl group of C2~C 60 Heteroaryl group, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, or condensed with adjacent groups to form a condensed ring,

[0016] Y1 to Y3 are the same or different from each other, and are each independently N or C(Ar3), provided that at least two of Y1 to Y3 are N,

[0017] Ar1 to Ar3 are the same or different and each independently represent hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a hydroxyl group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40Cycloalkyl group of C1~C 40 Heterocycloalkyl group, C6~C 60 Aryl group of C2~C 60 Heteroaryl group, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups;

[0018] n is an integer from 0 to 5,

[0019] Multiple L1s are identical or different from each other,

[0020] L1 is a single bond, or C6~C 60 Arylene group and C2~C 60 Selected from the group consisting of heteroarylene groups,

[0021] 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 to Ar3, the arylene group and heteroarylene group of the above L1, and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group and condensed ring of the above R1 to R4 are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, Amino group, hydroxyl group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C40 Cycloalkyl group of C1~C 40 Heterocycloalkyl group of dog, C6~C 60 Aryl group of C2~C 60 Heteroaryl group of dog, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 (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).

[0022] In addition, the present invention provides an organic electroluminescent device comprising an anode; a cathode; and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises the aforementioned organic compound.

[0023] For example, the organic layer including the organic compound may be an electron transport layer and / or an electron transport auxiliary layer.

[0024] As one embodiment of the present invention, the compound represented by the above chemical formula 1 can be used as an organic layer material of an organic electroluminescent device because it has excellent electron transport ability, luminescence ability, heat resistance, etc.

[0025] In particular, when the compound represented by the chemical formula 1 of the present invention is used as an electron transport layer or electron transport auxiliary layer material, it can exhibit high thermal stability, low driving voltage, fast mobility, high current efficiency, and long life characteristics compared to conventional host materials or electron transport materials.

[0026] Accordingly, the organic electroluminescent device including the compound of the above chemical formula 1 can be significantly improved in aspects such as excellent luminescence performance, low driving voltage, long life, and high efficiency, and thus can be effectively applied to full-color display panels, etc.

[0027] The effects according to the present invention are not limited to those exemplified above, and more diverse effects are included in this specification.

[0028] FIG. 1 is a cross-sectional view schematically showing an organic electroluminescent device according to a first embodiment of the present invention.

[0029] Figure 2 is a cross-sectional view schematically showing an organic electroluminescent device according to a second embodiment of the present invention.

[0030] FIG. 3 is a cross-sectional view schematically showing an organic electroluminescent device according to a third embodiment of the present invention.

[0031] <Explanation of symbols>

[0032] 100: positive, 200: negative,

[0033] 300: Organic layer, 310: Hole injection layer,

[0034] 320: hole transport layer, 330: light emitting layer,

[0035] 340: electron transport layer, 350: electron injection layer,

[0036] 360: Electron transport auxiliary layer

[0037] Hereinafter, the present invention will be described in detail.

[0038] <New organic compounds>

[0039] The compound according to the present invention provides a novel compound that can realize the characteristics of an organic electroluminescent device, such as high efficiency, long life, and low driving voltage, by having excellent electron injection and transport ability, electrochemical stability, thermal stability, etc.

[0040] Typically, in the light-emitting layer of an organic light-emitting device, electrons and holes combine to generate excitons. If the excitons thus generated are not blocked by the adjacent layer of the light-emitting layer, a decrease in the efficiency of the device will occur. In addition, if holes that should be generated in the hole injection layer and exist in the light-emitting layer move to the electron injection layer, a decrease in the efficiency and lifespan of the device will occur. At this time, if the organic material constituting the electron transport auxiliary layer or electron transport layer adjacent to the light-emitting layer has high singlet energy, triplet energy, and low HOMO energy, it can effectively block the excitons and holes generated in the light-emitting layer from moving to the electron transport layer, and this effect can be particularly evident in devices that use phosphorescent emitters rather than devices that use fluorescent emitters.

[0041] In order to solve the above-mentioned problem, the present invention has a structure in which a polycyclic spiro moiety and a nitrogen-containing heteroaromatic ring moiety are directly bonded to each other or bonded via a linker group, and is represented by the chemical formula 1.

[0042] Here, the polycyclic spiro moiety contains silicon (Si) at the spiro position and at least one heteroatom (e.g., O, S), such as spirobi[dibenzo[b,e][1,4]oxasiline], spirobi[dibenzo[b,e][1,4]thiasiline], spiro[dibenzo[b,e][1,4]oxasiline-10,10'- dibenzo[b,e][1,4]thiasiline], etc. As such, the polycyclic spiro moiety containing silicon (Si) at the spiro position has better conductivity than the spiro moiety having carbon at the spiro position [e.g., spirobixanthene moiety], and thus can improve electron mobility. In addition, the present invention can improve hole blocking characteristics because it has a deeper HOMO energy level than other spiro moieties by containing silicon (Si) at the spiro position. Therefore, the compound of the present invention can transfer electrons more quickly into the light-emitting layer, and the hole density in the light-emitting layer can also be improved due to the hole blocking effect from the light-emitting layer to the adjacent layer (e.g., electron transport layer, electron transport auxiliary layer). Therefore, the present invention can realize a low driving voltage and high efficiency of an organic electroluminescent device by increasing the number of excitons contributing to light emission.

[0043] In addition, the compound of the present invention can have physicochemical properties more suitable for electron injection and electron transport by including triazine or pyrimidine, which are functional groups having strong electron-withdrawing ability, thereby further improving the electron transfer rate.

[0044] In addition, since the compound represented by the chemical formula 1 of the present invention has a higher triplet energy (T1) than the light-emitting layer, it can prevent excitons generated in the light-emitting layer from diffusing (moving) to the adjacent electron transport layer or hole transport layer. Therefore, the number of excitons contributing to light emission increases, so that the light-emitting efficiency of the device can be improved, and the durability and stability of the device can be improved, so that the lifespan of the device can be efficiently increased. Most of the developed materials exhibit physical characteristics that enable low-voltage operation and also improve lifespan.

[0045] In addition, since the compound of the present invention includes a spiro moiety and a nitrogen-containing heteroaromatic moiety as well as various substituents on the moieties, it can have a high glass transition temperature (Tg) and thus improve the thermal stability of the device.

[0046] In addition, the compound of the present invention has an electron donating effect by the unshared electron pair of the heteroatom (O or S) included in the polycyclic spiro core structure. Therefore, when the compound of the present invention is applied to an organic electroluminescent device, it can improve the luminous efficiency of the device, and can realize a long life of the device by improving the durability and stability of the device. For example, when the compound of the present invention is applied as a material for an electron transport layer or an electron transport auxiliary layer, it can well accept electrons from the cathode and smoothly transfer electrons to the light-emitting layer, thereby lowering the operating voltage of the device and inducing high efficiency and long life.

[0047] As described above, when the compound represented by the chemical formula 1 of the present invention is applied as an organic layer material of an organic electroluminescent device, preferably an emitting layer material (a blue, green and / or red phosphorescent host material), an electron transport layer / injection layer material, a hole transport layer / injection layer material, an emitting auxiliary layer material, or a life-span improvement layer material, the performance and life-span characteristics of the organic electroluminescent device can be significantly improved. In particular, when the compound of the present invention is used as an electron transport layer or an electron transport auxiliary layer material, a significantly superior performance improvement effect in terms of the efficiency, driving voltage, and life-span characteristics of the device can be expected. As a result, such an organic electroluminescent device can maximize the performance of a full-color organic light-emitting panel.

[0048]

[0049] The compound represented by chemical formula 1 according to the present invention forms a basic skeletal structure by directly or through a separate linker (L) combining a polycyclic spiro moiety having excellent conductivity and a nitrogen-containing heteroaromatic ring moiety, which is an electron-withdrawing group (EWG) having excellent electron transport ability.

[0050] The above polycyclic spiro ring moiety (X1 and X2-containing ring moiety) contains Si at the spiro position and at least one heteroatom (e.g., O, S), wherein X1 and X2 are the same as or different from each other and are each independently O or S. An example of such a spiro ring moiety may be selected from the group consisting of the following moieties Mo1-1 to Mo1-4.

[0051]

[0052] In the above moieties Mo1-1 to Mo1-4,

[0053] * indicates a site that is combined with the above chemical formula 1,

[0054] o, p, q, r and R1 to R4 are each as defined in the above chemical formula 1.

[0055] The hydrogen(s) of the above spiro ring moiety may be substituted or unsubstituted with various substituents R1 to R4.

[0056] If o is 0, it means that hydrogen is not substituted with the substituent R1, if p is 0, it means that hydrogen is not substituted with the substituent R2, if q is 0, it means that hydrogen is not substituted with the substituent R3, and if r is 0, it means that hydrogen is not substituted with the substituent R4. On the other hand, if o is an integer from 1 to 3, specifically 1 or 2, it means that hydrogen is substituted with the substituent R1, if p is an integer from 1 to 4, specifically 1 or 2, it means that hydrogen is substituted with the substituent R2, if q is an integer from 1 to 4, specifically 1 or 2, it means that hydrogen is substituted with the substituent R3, and if r is an integer from 1 to 4, specifically 1 or 2, it means that hydrogen is substituted with the substituent R4. At this time, multiple R1, multiple R2, multiple R3 and multiple R4 are the same or different from each other.

[0057] R1 to R4 are the same or different and each independently represent hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of C1~C 40 Heterocycloalkyl group, C6~C 60 Aryl group of C2~C 60 Heteroaryl group, C1~C 40 Alkyloxy group, C6~C60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or is condensed with adjacent groups (e.g., R1-R1, R2-R2, R3-R3, R4-R4, etc.) to form a condensed ring. Here, the heteroatom may be N, O, or S. Meanwhile, the condensed ring may be C3~C 60 Condensed aliphatic rings (specifically, C3~C 30 condensed aliphatic ring), C6~C 60 Condensed aromatic rings (specifically, C6~C 30 A 5- to 60-membered fused heteroaromatic ring containing a heteroatom such as N, O or S (specifically, a 5- to 30-membered fused heteroaromatic ring), C3~C 60 It may be at least one selected from the group consisting of spiro rings and combinations thereof.

[0058] Specifically, R1 to R4 are the same or different from each other, and each independently represents hydrogen, deuterium (D), cyano group (-CN), C1~C 20 Alkyl group of C3~C 20 Cycloalkyl group of C1~C 20 Heterocycloalkyl group, C6~C 30 Aryl group and C2~C 30 Selected from the group consisting of heteroaryl groups, or condensed with adjacent groups (e.g. R1-R1, R2-R2, R3-R3, R4-R4, etc.) to form C6~C 30 It can form a condensed aromatic ring or a condensed heteroaromatic ring of 5 to 30 members.

[0059] More specifically, R1 to R4 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium (D), a cyano group (-CN), a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophene group, a fluorene group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group, or may be condensed with an adjacent group (e.g., R1-R1, R2-R2, R3-R3, R4-R4, etc.) to form a 6-18 membered condensed aromatic ring or a 6-18 membered condensed heteroaromatic ring containing a heteroatom of N, O, or S.

[0060] At this time, 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, arylamine group and condensed ring of R1 to R4 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1 to C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of C1~C 40 Heterocycloalkyl group, C6~C 60 Aryl group of C2~C 60 Heteroaryl group, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60Arylphosphine oxide group and C6~C 60 Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and specifically, each independently selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group of C2~C 30 Heteroaryl group, C6~C 30 Arylphosphine oxide group and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups. If there are multiple substituents, they may be the same or different.

[0061] Another example of the above spiro ring moiety may be selected from the group consisting of the following moieties Mo2-1 to Mo2-36, depending on the presence or absence of a condensed ring with the adjacent groups o, p, q, r and R1 to R4 described above. However, the present invention is not limited thereto.

[0062]

[0063]

[0064]

[0065]

[0066]

[0067] In the above moieties Mo2-1 to Mo2-36,

[0068] * indicates a site that is combined with the above chemical formula 1,

[0069] R1 to R4 are each as defined in the above chemical formula 1,

[0070] Ring Cy1 is a condensed ring condensed on a benzene ring, and is selected from the group consisting of a 6- to 18-membered condensed aromatic ring and a 5- to 18-membered condensed heteroaromatic ring, and specifically may be selected from the group consisting of the following condensed rings Cy2-1 to Cy2-7, wherein the dotted line (---) indicates a portion bonded to the benzene ring of the moieties Mo2-1 to Mo2-36.

[0071]

[0072] In the compound represented by Chemical Formula 1 according to the present invention, the nitrogen-containing heteroaromatic ring moiety (Y1 to Y3-containing ring moiety) contains 2 to 3 nitrogen atoms and is an electron-withdrawing group (EWG) with excellent electron transport ability. In this nitrogen-containing heteroaromatic ring moiety, Y1 to Y3 are the same as or different from each other, and are each independently N or C(Ar3), provided that at least two of Y1 to Y3 are N. Due to this nitrogen-containing heteroaromatic ring moiety, the compound of the present invention exhibits excellent electron absorption properties, which is advantageous for electron injection and transport.

[0073] For example, the Y1 to Y3-containing ring moiety may be selected from the group consisting of the following moieties Az1-1 to Az1-3.

[0074]

[0075] In the above moieties Az1-1 to Az1-3,

[0076] * indicates a site that is combined with the above chemical formula 1,

[0077] Ar1 to Ar3 are each as defined in the above chemical formula 1.

[0078] In the above-mentioned nitrogen-containing heteroaromatic ring moiety (Y1 to Y3-containing ring moiety), Ar1 to Ar3 are the same or different from each other, and each independently represents hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of C1~C 40 Heterocycloalkyl group, C6~C 60 Aryl group of C2~C 60 Heteroaryl group, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, and specifically, each independently hydrogen, deuterium (D), C1~C 20 Alkyl group of C6~C 30 Aryl group of C2~C 30 Heteroaryl group, C6~C 30 Arylphosphine oxide group and C6~C 30It can be selected from the group consisting of arylamine groups, and more specifically, it can be selected from the group consisting of hydrogen, deuterium (D), phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenylenyl group, phenanthryl group, fluorenyl group, anthracenyl group, anthryl group, pyrenyl group, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, dibenzofuran group, dibenzothiophene group, phenanthrolinyl group, and carbazolyl group, each independently.

[0079] At this time, 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 to Ar3 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1 to C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of C1~C 40 Heterocycloalkyl group, C6~C 60 Aryl group of C2~C 60 Heteroaryl group, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and specifically, each independently selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group of C2~C 30 Heteroaryl group, C6~C 30 Arylphosphine oxide group and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups. If there are multiple substituents, they may be the same or different.

[0080] For example, Ar1 and Ar2 are the same or different from each other, and are each independently C6~C 60 Aryl group and C2~C 60 It can be selected from the group consisting of heteroaryl groups of Ar1 and Ar2, and the aryl group and heteroaryl group of Ar1 and Ar2 are deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group of C2~C 30 Heteroaryl group, C6~C 30 Arylphosphine oxide group and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups. If there are multiple substituents, they may be the same or different.

[0081] In another example, Ar1 and Ar2 may be the same or different and may each be independently selected from the group consisting of the following substituents S1-1 to S1-21, but are not limited thereto.

[0082]

[0083] In the above substituents S1-1 to S1-21,

[0084] * indicates a site that is combined with the above chemical formula 1,

[0085] a is an integer from 0 to 5, specifically an integer from 0 to 3,

[0086] b is an integer from 0 to 4, specifically an integer from 0 to 2,

[0087] c is an integer from 0 to 7, specifically an integer from 0 to 4, and more specifically an integer from 0 to 2,

[0088] d is an integer from 0 to 6, specifically an integer from 0 to 3,

[0089] e is an integer from 0 to 3, specifically an integer from 0 to 2,

[0090] f is an integer from 0 to 2, specifically 0 or 1,

[0091] g is an integer from 0 to 9, specifically an integer from 0 to 4, and more specifically an integer from 0 to 2,

[0092] h is an integer from 0 to 11, specifically an integer from 0 to 5, and more specifically an integer from 0 to 3,

[0093] Multiple R's are the same or different from each other,

[0094] R is hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of C1~C 40 Heterocycloalkyl group, C6~C 60 Aryl group of C2~C 60 Heteroaryl group, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, specifically hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group of C2~C 30 Heteroaryl group, C6~C 30 Arylphosphine oxide group and C6~C 30It can be selected from the group consisting of arylamine groups, and more specifically, hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, adamantyl group, norbornyl, bicyclo[1.1.0]butyl group, bicyclo[2.2.0]hexyl group, bicyclo[2.2.1]hexyl group, bicyclo[3.1.0]hexyl group, bicyclo[1.2.1]hexyl group, bicyclo[3.1.0]hexyl group, bicyclo[2.2.2]octyl group, bicyclo[3.1.1]heptyl group, It can be selected from the group consisting of a bicyclo[3.2.1]octyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophene group, and a fluorene group.

[0095] In another example, Ar1 and Ar2 may be the same or different and may each be independently selected from the group consisting of the following substituents S2-1 to S2-36, but are not limited thereto.

[0096]

[0097]

[0098]

[0099] In the above substituents S2-1 to S2-36,

[0100] * indicates a site that is combined with the above chemical formula 1,

[0101] a1 is an integer from 1 to 5,

[0102] b1 is an integer from 1 to 9.

[0103] The above substituents S2-1 to S2-36 are each deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), C1~C 12Alkyl group of C6~C 10 aryl group, and C2~C 10 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl groups.

[0104] In the compound represented by Chemical Formula 1 according to the present invention, a spiro ring moiety having excellent conductivity (e.g., an X1 to X2-containing ring moiety) and a nitrogen-containing heteroaromatic ring moiety having excellent electron transport ability and EWG characteristics (e.g., a Y1 to Y3-containing ring moiety) are directly bonded or bonded via a separate linker (e.g., L1). When the linker (L) is present, the HOMO region is expanded, which provides a benefit to the HOMO-LUMO distribution, and charge transfer efficiency can be increased through appropriate HOMO-LUMO overlap. In addition, the stability of the molecule can be increased.

[0105] If n is 0, it means that L1 is a single bond (direct bond). On the other hand, if n is an integer from 1 to 5, L1 is a divalent linker group, C1~C 60 alkylene group, C6~C 60 Arylene group and C2~C 60 Selected from the group consisting of heteroarylene groups, specifically C1~C 30 alkylene group, C6~C 30 Arylene group and C2~C 30 It can be selected from the group consisting of heteroarylene groups. Here, multiple L1s can be the same or different from each other.

[0106] The alkylene group, arylene group and heteroarylene group of the above L1 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C40 Cycloalkyl group of C1~C 40 Heterocycloalkyl group, C6~C 60 Aryl group of C2~C 60 Heteroaryl group, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and specifically, each of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group of C2~C 30 Heteroaryl group, C6~C 30 Arylphosphine oxide group and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups. If there are multiple substituents, they may be the same or different.

[0107] According to an example, the L1 may be a single bond or may be selected from the group consisting of a phenylene group, a biphenylene group, a terphenylene group, a naphthalene group, a phenanthrene group, a triphenylene group, a fluorene group, and a combination thereof, but is not limited thereto. Here, the hydrogen of the phenylene group, the biphenylene group, the terphenylene group, the naphthalene group, the phenanthrene group, the triphenylene group, and the fluorene group may be deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), C1~C 12 Alkyl group of C6~C 10 aryl group, and C2~C10 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl groups. Here, multiple L1s may be the same or different from each other.

[0108] According to another example, the L1 may be a single bond or a linker group L1-1, and multiple L1s may be the same or different from each other.

[0109]

[0110] In the above linker group L1-1,

[0111] * indicates a site that is combined with the above chemical formula 1,

[0112] i is an integer from 0 to 4, specifically an integer from 0 to 2,

[0113] Multiple R's are the same or different from each other,

[0114] R is hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of C1~C 40 Heterocycloalkyl group, C6~C 60 Aryl group of C2~C 60 Heteroaryl group, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60Selected from the group consisting of arylamine groups, specifically hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group of C2~C 30 Heteroaryl group, C6~C 30 Arylphosphine oxide group and C6~C 30 It can be selected from the group consisting of arylamine groups, and more specifically, hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, adamantyl group, norbornyl, bicyclo[1.1.0]butyl group, bicyclo[2.2.0]hexyl group, bicyclo[2.2.1]hexyl group, bicyclo[3.1.0]hexyl group, bicyclo[1.2.1]hexyl group, bicyclo[3.1.0]hexyl group, bicyclo[2.2.2]octyl group, bicyclo[3.1.1]heptyl group, It can be selected from the group consisting of a bicyclo[3.2.1]octyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophene group, and a fluorene group.

[0115] According to another example, the L1 may be a single bond or may be selected from the group consisting of linker groups L2-1 to L2-27, but is not limited thereto.

[0116]

[0117] In the above linker groups L2-1 to L2-27,

[0118] * indicates a part that is combined with the above chemical formula 1.

[0119] The above linker groups L2-1 to L2-27 are deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), C1~C 12 Alkyl group of C6~C 10 aryl group, and C2~C 10 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl groups.

[0120] According to an example of the present invention, the compound represented by the above chemical formula 1 may be a compound represented by any one of the following chemical formulas 2 to 5, depending on the bonding position between the X1 and X2-containing ring moieties and L1.

[0121]

[0122]

[0123]

[0124]

[0125] In the above chemical formulas 2 to 5,

[0126] X1, X2, o, p, q, r, R1 to R4, Y1, Y2, Y3, Ar1, Ar2, n, L1 are each as defined in the above chemical formula 1.

[0127] According to another example of the present invention, the compound represented by the above chemical formula 1 may be a compound represented by any one of the following chemical formulas 6 to 14, depending on the bonding position between the X1 and X2-containing ring moieties and L1, and the type of the Y1 to Y2-containing ring moiety. However, the present invention is not limited thereto.

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140] In the above chemical formulas 6 to 17,

[0141] X1, X2, o, p, q, r, R1 to R4, Ar1, Ar2, n, L1 are each as defined in the above chemical formula 1.

[0142] According to another example of the present invention, the compound represented by the above chemical formula 1 may be a compound represented by any one of the following chemical formulas 18 to 20, depending on the bonding position between X1 and X2-containing ring moieties and L1, the type of L1, and the type of Y1 to Y2-containing ring moieties. However, the present invention is not limited thereto.

[0143]

[0144]

[0145]

[0146] In the above chemical formulas 18 to 20,

[0147] X1, X2, o, p, q, r, R1 to R4, Ar1, Ar2, n are each as defined in the above chemical formula 1,

[0148] i is an integer from 0 to 4, specifically an integer from 0 to 2,

[0149] Multiple R's are the same or different from each other,

[0150] R is hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of C1~C 40 Heterocycloalkyl group, C6~C 60 Aryl group of C2~C 60 Heteroaryl group, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, specifically hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group of C2~C 30 Heteroaryl group, C6~C 30 Arylphosphine oxide group and C6~C 30It can be selected from the group consisting of arylamine groups, and more specifically, hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, adamantyl group, norbornyl, bicyclo[1.1.0]butyl group, bicyclo[2.2.0]hexyl group, bicyclo[2.2.1]hexyl group, bicyclo[3.1.0]hexyl group, bicyclo[1.2.1]hexyl group, bicyclo[3.1.0]hexyl group, bicyclo[2.2.2]octyl group, bicyclo[3.1.1]heptyl group, It can be selected from the group consisting of a bicyclo[3.2.1]octyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophene group, and a fluorene group.

[0151] According to another example of the present invention, the compound represented by the above chemical formula 1 may be a compound represented by any one of the following chemical formulas 21 to 32, depending on the types of X1 and X2-containing ring moieties, the bonding positions between the X1 and X2-containing ring moieties and L1, the type of L1, and the types of Y1 to Y2-containing ring moieties. However, the present invention is not limited thereto.

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164] In the above chemical formulas 21 to 32,

[0165] o, p, q, r, R1 to R4, Ar1, Ar2, n are each as defined in the above chemical formula 1,

[0166] i is an integer from 0 to 4, specifically an integer from 0 to 2,

[0167] Multiple R's are the same or different from each other,

[0168] R is as defined in the above chemical formulas 18 to 20.

[0169] According to another example of the present invention, the compound represented by the above chemical formula 1 may be a compound represented by any one of the following chemical formulas 33 to 59, depending on the types of X1 and X2-containing ring moieties, the types of o, p, q, and r, whether a condensed ring is formed with adjacent groups of R1 to R4, the bonding position between X1 and X2-containing ring moieties and L1, the type of L1, and the type of Y1 to Y2-containing ring moiety. However, the present invention is not limited thereto.

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197] In the above chemical formulas 33 to 59,

[0198] R1 to R4, Ar1, Ar2, and n are each as defined in the above chemical formula 1,

[0199] i is an integer from 0 to 4, specifically an integer from 0 to 2,

[0200] Multiple R's are the same or different from each other,

[0201] R is as defined in the above chemical formulas 18 to 20,

[0202] Ring Cy1 is a condensed ring condensed on a benzene ring, and is selected from the group consisting of a 6- to 18-membered condensed aromatic ring and a 5- to 18-membered condensed heteroaromatic ring, and specifically, may be selected from the group consisting of the following condensed rings Cy2-1 to Cy2-7, wherein the dotted lines of the following condensed rings Cy2-1 to Cy2-7 indicate a portion bonded to the benzene ring of the above chemical formulae 33 to 59.

[0203]

[0204] The compound represented by the chemical formula 1 of the present invention described above can be further specified as compounds 1 to 165 below, but is not limited thereto.

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212] In the present invention, the "number of nuclear atoms" refers to the number of ring atoms constituting a ring structure, and the nuclear atoms may be carbon or a heteroatom selected from the group consisting of N, O, S, and Se. For example, the number of nuclear atoms of pyridine refers to 6, including 5 C and 1 N constituting the pyridine ring.

[0213] 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.

[0214] 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.

[0215] 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.

[0216] 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 adamantyl.

[0217] In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 1 to 40 carbon atoms, wherein at least one carbon atom in the ring, preferably 1 to 3 carbons, 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. Such a heterocycloalkyl group having 1 to 40 carbon atoms can also be expressed as a heterocycloalkyl group having 3 to 40 nuclear atoms. Here, the number of nuclear atoms means the number of atoms forming the ring, i.e., the number of ring atoms.

[0218] 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.

[0219] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 1 to 60 carbon atoms. At this time, at least one carbon atom in the ring, preferably 1 to 3 carbon atom(s), 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, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, and 2-pyrimidinyl. These heteroaryl groups having 1 to 60 carbon atoms can also be expressed as heteroaryl groups having 5 to 60 nuclear atoms. Here, the number of nuclear atoms means the number of atoms forming the ring, i.e., the number of ring atoms.

[0220] 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.

[0221] 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.

[0222] 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.

[0223] In addition, "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms, and includes polyarylsilyl such as mono-, di-, and tri-arylsilyl.

[0224] 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.

[0225] 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.

[0226] In addition, in the present invention, “arylphosphinyl group” means a phosphine group substituted with an aryl having 6 to 60 carbon atoms, and includes not only mono- but also di-arylphosphinyl groups.

[0227] In the present invention, “arylphosphine oxide group” means a phosphine oxide group substituted with an aryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylphosphine oxide groups.

[0228] 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.

[0229] 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 1 to 60 carbon atoms, a fused heteroaromatic ring having 2 to 60 carbon atoms, a spiro ring having 3 to 60 carbon atoms, or a combination thereof. The fused heteroaliphatic ring having 1 to 60 carbon atoms may be expressed as a fused heteroaliphatic ring having 3 to 60 nuclear atoms, and the fused heteroaromatic ring having 2 to 60 carbon atoms may be expressed as a fused heteroaromatic ring having 5 to 60 nuclear atoms. Here, the number of nuclear atoms means the number of atoms forming the ring, i.e., the number of ring atoms.

[0230]

[0231] Organic electroluminescent devices

[0232] Meanwhile, the present invention provides an organic electroluminescent device (hereinafter, 'organic EL device') comprising a compound represented by the above-described chemical formula 1.

[0233] Specifically, the organic electroluminescent device according to the present invention includes an anode (100), a cathode (200), and one or more organic layers (300) interposed between the anode and the cathode, as illustrated in FIGS. 1 to 3, and at least one of the one or more organic layers includes a compound represented by the chemical formula 1. At this time, the compound may be used alone, or two or more may be mixed and used.

[0234] The organic layer (300) of one or more layers may include one or more of a hole injection layer (310), a hole transport layer (320), a light-emitting layer (330), an electron transport auxiliary layer (360), an electron transport layer (340), and an electron injection layer (350), and at least one of the organic layers (300) includes a compound represented by the chemical formula 1. Specifically, the organic layer including the compound represented by the chemical formula 1 may be at least one of the light-emitting layer (330), the electron transport layer (340), and the electron transport auxiliary layer (360).

[0235] According to an example, the organic material layer of one or more layers may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and may optionally further include an electron transport auxiliary layer. The electron transport layer includes a compound represented by the above chemical formula 1. In this case, the compound represented by the above chemical formula 1 is included in the organic electroluminescent device as an electron transport layer material. In such an organic electroluminescent device, electrons can be easily injected from the cathode or the electron injection layer to the electron transport layer due to the compound represented by the above chemical formula 1, and can also quickly move from the electron transport layer to the light emitting layer, so that the binding force between holes and electrons in the light emitting layer is high. Therefore, the organic electroluminescent device of the present invention is excellent in luminous efficiency, power efficiency, brightness, etc. In addition, the compound represented by the above chemical formula 1 has excellent thermal stability and electrochemical stability, and can improve the performance of the organic electroluminescent device.

[0236] The compound represented by the chemical formula 1 may be used alone or mixed with an electron transport layer material known in the art.

[0237] In the present invention, the electron transport layer material that can be mixed with the compound represented by the above chemical formula 1 includes an electron transport material commonly known in the art. Non-limiting examples of the electron transport material that can be used include an oxazole compound, an isoxazole compound, a triazole compound, an isothiazole compound, an oxadiazole compound, a thiadiazole compound, a perylene compound, and an aluminum complex (e.g., Alq). 3, tris(8-quinolinolato)-aluminium), gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. These can be used alone or in combination of two or more.

[0238] In the present invention, when the compound represented by the above chemical formula 1 and the electron transport layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0239] According to another example, the organic layer of one or more layers includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, and the electron transport auxiliary layer includes a compound represented by the chemical formula 1. At this time, the compound represented by the chemical formula 1 is included in an organic electroluminescent device as an electron transport auxiliary layer material. At this time, the compound represented by the chemical formula 1 has a high triplet energy. Therefore, when the compound represented by the chemical formula 1 is included as an electron transport auxiliary layer material, the efficiency of the organic electroluminescent device can be increased due to the TTF (triplet-triplet fusion) effect. In addition, the compound represented by the chemical formula 1 can prevent excitons or holes generated in the light emitting layer from diffusing to the electron transport layer adjacent to the light emitting layer. Therefore, the number of excitons contributing to light emission in the light emitting layer increases, so that the light emitting efficiency of the device can be improved, and the durability and stability of the device can be improved, so that the lifespan of the device can be efficiently increased.

[0240] The compound represented by the chemical formula 1 may be used alone or mixed with an electron transport layer auxiliary layer material known in the art.

[0241] In the present invention, the electron transport auxiliary layer material that can be mixed with the compound represented by the above chemical formula 1 includes electron transport materials commonly known in the art, such as oxadiazole derivatives, triazole derivatives, phenanthroline derivatives (e.g., BCP), and heterocyclic derivatives containing nitrogen, but is not limited thereto.

[0242] The structure of the organic electroluminescent device of the present invention described above is not particularly limited, but for example, an anode (100), one or more organic layers (300), and a cathode (200) may be sequentially laminated on a substrate (see FIGS. 1 to 3). In addition, although not shown, it may have a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.

[0243] According to an example, the organic electroluminescent device may have a structure in which an anode (100), a hole injection layer (310), a hole transport layer (320), a light-emitting layer (330), an electron transport layer (340), and a cathode (200) are sequentially laminated on a substrate, as illustrated in FIG. 1. Optionally, as illustrated in FIG. 2, an electron injection layer (350) may be positioned between the electron transport layer (340) and the cathode (200). In addition, an electron transport auxiliary layer (360) may be positioned between the light-emitting layer (330) and the electron transport layer (340) (see FIG. 3).

[0244] The organic electroluminescent device of the present invention can be manufactured by forming the organic layer and the electrode using materials and methods known in the art, except that at least one of the organic layers (300) [e.g., the light-emitting layer (330), the electron transport layer (340), or the electron transport auxiliary layer (360)] includes a compound represented by the chemical formula 1.

[0245] The above organic layer can be formed by vacuum deposition or solution coating. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

[0246] The substrate usable in the present invention is not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, etc.

[0247] Examples of anode materials include, but are not limited to, metals such as vanadium, chromium, copper, zinc, gold, or 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 or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black.

[0248] Examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin, or lead, or alloys thereof; and multilayered materials such as LiF / Al or LiO2 / Al.

[0249] In addition, the hole injection layer, hole transport layer, light emitting layer, and electron injection layer are not particularly limited, and conventional materials known in the art can be used.

[0250]

[0251] 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.

[0252] [Preparation Example 1] Synthesis of Compound Core 1

[0253] <Step 1> Synthesis of 10,10-dichloro-10H-dibenzo[b,e][1,4]oxasiline

[0254]

[0255] Under a nitrogen atmosphere, 50 g (152.44 mmol) of 2,2'-oxybis(bromobenzene) was added to 500 ml (0.3 M) of tetrahydrofuran, and the temperature was lowered to -80 °C while stirring. At the same temperature, 200 ml (320.12 mmol, 1.6 M in hexane solution) of n-BuLi was added dropwise and stirred for about 1 hour. Then, a mixed solution of 21.26 ml (167.68 mmol) of SiCl4 and 60 ml of THF was added dropwise and stirred for another 30 minutes. After 30 minutes, the temperature was increased to room temperature and stirred for about 5 hours. After completion of the reaction, the solid was filtered under reduced pressure from the reaction solution, and the obtained solid was dissolved in 250 ml of dichloromethane, the precipitate was filtered, and the filtrate was concentrated under reduced pressure to obtain 23.22 g (yield 57%) of the target compound.

[0256] Mass: [(M+H) + ] : 267

[0257] <Step 2> Synthesis of 2-chloro-10,10'-spirobi[dibenzo[b,e][1,4]oxasiline]

[0258]

[0259] Under a nitrogen atmosphere, 37.8 g (104.29 mmol) of 2-bromo-1-(2-bromophenoxy)-4-chlorobenzene was added to 300 ml (0.3 M) of THF, and the temperature was lowered to -80 °C while stirring. At the same temperature, 114 ml (182.51 mmol, 1.6 M in hexane solution) of n-BuLi was added dropwise, and the mixture was stirred for about 1 hour. Then, a mixed solution of 23.22 g (86.91 mmol) of 10,10-dichloro-10H-dibenzo[b,e][1,4]oxasiline and 50 ml of THF was added dropwise, and the mixture was stirred for another 30 minutes. After 30 minutes, the mixture was heated to room temperature, and the mixture was stirred for about 5 hours. After the reaction was completed, the reaction solution was added dropwise to 350 ml of NaHCO3 aqueous solution cooled to below 0°C and stirred at the same temperature for 30 minutes. After stirring, extraction was performed with dichloromethane and MgSO4 was added to remove moisture. The extracted reaction solution was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then concentrated under reduced pressure again to obtain 17.68 g (yield 51%) of the target compound.

[0260] Mass: [(M+H) + ] : 400

[0261] <Step 3> Synthesis of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10,10'-spirobi[dibenzo[b,e][1,4]oxasiline] (Core 1)

[0262]

[0263] 2-chloro-10,10'-spirobi[dibenzo[b,e][1,4]oxasiline] 17.68 g (44.32 mmol), Bis(pinacolato)diboron(BPDB) 22.51 g (88.64 mmol), Pd(dppf)Cl2 0.97 g (1.33 mmol), X-Phos 1.27 (2.66 mmol), and KOAc 13.05 g (132.96 mmol) were added to 250 ml of 1,4-dioxane and heated under reflux for 6 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane to obtain 15 g (yield 69%) of the target compound.

[0264] Mass: [(M+H) + ] : 491

[0265]

[0266] [Preparation Example 2] Synthesis of Compound Core 2

[0267]

[0268] In <Step 1> of Preparation Example 1, bis(2-bromophenyl)sulfane was used instead of 2,2'-oxybis(bromobenzene), 10,10-dichloro-10H-dibenzo[b,e][1,4]thiasiline was used instead of 10,10-dichloro-10H-dibenzo[b,e][1,4]oxasiline, 2-bromo-1-(2-bromophenoxy)-4-chlorobenzene was used instead of 2-bromo-1-(2-bromophenoxy)-4-chlorobenzene, and 2-chloro-10,10'-spirobi[dibenzo[b,e][1,4]oxasiline] was used instead of Except for using 2-chlorospiro[dibenzo[b,e][1,4]oxasiline-10,10'-dibenzo[b,e][1,4]thiasiline], the same process as in [Preparation Example 1] was performed to obtain 13.36 g (yield 73%) of the target compound.

[0269] Mass: [(M+H) + ] : 507

[0270]

[0271] [Preparation Example 3] Synthesis of Compound Core 3

[0272]

[0273] In <Step 1> of Preparation Example 1, 2,2'-oxybis(bromobenzene) is used instead of 2,2'-oxybis(bromobenzene), 10,10-dichloro-10H-dibenzo[b,e][1,4]oxasiline is used instead of 10,10-dichloro-10H-dibenzo[b,e][1,4]oxasiline used in <Step 2>, (2-bromo-4-chlorophenyl)(2-bromophenyl)sulfane is used instead of 2-bromo-1-(2-bromophenoxy)-4-chlorobenzene, and 2-chloro-10,10'-spirobi[dibenzo[b,e][1,4]oxasiline] used in <Step 3> Except for using 2'-chlorospiro[dibenzo[b,e][1,4]oxasiline-10,10'-dibenzo[b,e][1,4]thiasiline], the same process as in [Preparation Example 1] was performed to obtain 12.08 g (yield 66%) of the target compound.

[0274] Mass: [(M+H) + ] : 507

[0275]

[0276] [Preparation Example 4] Synthesis of Compound Core 4

[0277]

[0278] Except that bis(2-bromophenyl)sulfane was used instead of 2,2'-oxybis(bromobenzene) used in <Step 1> of Preparation Example 1, 10,10-dichloro-10H-dibenzo[b,e][1,4]thiasiline was used instead of 10,10-dichloro-10H-dibenzo[b,e][1,4]oxasiline used in <Step 2>, (2-bromo-4-chlorophenyl)(2-bromophenyl)sulfane was used instead of 2-bromo-1-(2-bromophenoxy)-4-chlorobenzene, and 2-chloro-10,10'-spirobi[dibenzo[b,e][1,4]thiasiline] was used instead of 2-chloro-10,10'-spirobi[dibenzo[b,e][1,4]oxasiline] used in <Step 3>, [Preparation Example 1] The same process was performed to obtain 13.09 g (yield 72%) of the target compound.

[0279] Mass: [(M+H) + ] : 523

[0280]

[0281] [Preparation Example 5] Synthesis of Compound Core 5

[0282]

[0283] Except that 2,2'-oxybis(bromobenzene) is used instead of 2,2'-oxybis(bromobenzene) used in <Step 1> of Preparation Example 1, 10,10-dichloro-10H-dibenzo[b,e][1,4]oxasiline is used instead of 10,10-dichloro-10H-dibenzo[b,e][1,4]oxasiline used in <Step 2>, 1-bromo-2-(2-bromophenoxy)-4-chlorobenzene is used instead of 2-bromo-1-(2-bromophenoxy)-4-chlorobenzene, and 3-chloro-10,10'-spirobi[dibenzo[b,e][1,4]oxasiline] is used instead of 2-chloro-10,10'-spirobi[dibenzo[b,e][1,4]oxasiline] used in <Step 3>, The same process as in [Preparation Example 1] above was performed to obtain 14.02 g (yield 76%) of the target compound.

[0284] Mass: [(M+H)+]: 491

[0285]

[0286] [Preparation Example 6] Synthesis of Compound Core 6

[0287]

[0288] In <Step 1> of Preparation Example 1, 2,2'-oxybis(bromobenzene) is used instead of 2,2'-oxybis(bromobenzene), 10,10-dichloro-10H-dibenzo[b,e][1,4]oxasiline is used instead of 10,10-dichloro-10H-dibenzo[b,e][1,4]oxasiline used in <Step 2>, (2-bromo-5-chlorophenyl)(2-bromophenyl)sulfane is used instead of 2-bromo-1-(2-bromophenoxy)-4-chlorobenzene, and 2-chloro-10,10'-spirobi[dibenzo[b,e][1,4]oxasiline] used in <Step 3> Except for using 3'-chlorospiro[dibenzo[b,e][1,4]oxasiline-10,10'-dibenzo[b,e][1,4]thiasiline], the same process as in [Preparation Example 1] was performed to obtain 13 g (yield 71%) of the target compound.

[0289] Mass: [(M+H)+]: 507

[0290]

[0291] [Preparation Example 7] Synthesis of Compound Core 7

[0292]

[0293] Except that bis(2-bromophenyl)sulfane is used instead of 2,2'-oxybis(bromobenzene) used in <Step 1> of Preparation Example 1, 10,10-dichloro-10H-dibenzo[b,e][1,4]thiasiline is used instead of 10,10-dichloro-10H-dibenzo[b,e][1,4]oxasiline used in <Step 2>, (2-bromo-5-chlorophenyl)(2-bromophenyl)sulfane is used instead of 2-bromo-1-(2-bromophenoxy)-4-chlorobenzene, and 3-chloro-10,10'-spirobi[dibenzo[b,e][1,4]thiasiline] is used instead of 2-chloro-10,10'-spirobi[dibenzo[b,e][1,4]oxasiline] used in <Step 3>, [Preparation Example 1] The same process was performed to obtain 12.55 g (yield 68%) of the target compound.

[0294] Mass: [(M+H)+]: 523

[0295]

[0296] [Synthesis Example 1] Synthesis of Compound 7

[0297]

[0298] 9.5 g (27.63 mmol) of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine and 15 g (30.39 mmol) of Core 1, the compound synthesized in Preparation Example 1, were added to 100 ml of THF and 50 ml of H2O. 40.96 g (0.83 mmol) of Pd(PPh3) and 11.46 g (224.11 mmol) of K2CO3 were added, and the mixture was heated and refluxed for 6 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, dried over MgSO4, and filtered. The obtained reaction solution was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane to obtain 13.12 g (yield 70%) of the target compound.

[0299] Mass: [(M+H)+]: 672

[0300]

[0301] [Synthesis Example 2] Synthesis of Compound 20

[0302]

[0303] 9.3 g (23.95 mmol) of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine and 13.36 g (26.35 mmol) of Core 2, the compound synthesized in Preparation Example 2, were added to 100 ml of toluene, 50 ml of EtOH, and 50 ml of H2O. 20.16 g (0.72 mmol) of Pd(OAC), 0.69 g (1.44 mmol) of X-Phos, and 23.41 g (71.86 mmol) of Cs2CO3 were added, and the mixture was heated and refluxed for 6 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, dried over MgSO4, and filtered. The obtained reaction solution was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane to obtain 13.35 g (yield 81%) of the target compound.

[0304] Mass: [(M+H)+]: 688

[0305]

[0306] [Synthesis Example 3] Synthesis of Compound 21

[0307]

[0308] Except that 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2, and that compound Core 1 synthesized in Preparation Example 1 was used instead of compound Core 2, the same procedure as in Synthesis Example 2 was performed to obtain 13.5 g (yield 78%) of the target compound.

[0309] Mass: [(M+H)+]: 672

[0310]

[0311] [Synthesis Example 4] Synthesis of Compound 35

[0312]

[0313] Except that 2-(2'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2, and that compound Core 1 synthesized in Preparation Example 1 was used instead of compound Core 2, the same procedure as in Synthesis Example 2 was performed to obtain 14.96 g (yield 84%) of the target compound.

[0314] Mass: [(M+H)+]: 748

[0315]

[0316] [Synthesis Example 5] Synthesis of Compound 44

[0317]

[0318] Except that 2-(2''-chloro-[1,1':2',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2, and that compound Core 1 synthesized in Preparation Example 1 was used instead of compound Core 2, the same procedure as in Synthesis Example 2 was performed to obtain 12.79 g (yield 77%) of the target compound.

[0319] Mass: [(M+H)+]: 824

[0320]

[0321] [Synthesis Example 6] Synthesis of Compound 45

[0322]

[0323] Except for using 2-(3''-chloro-[1,1':2',1''-terphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2, the same procedure as in Synthesis Example 2 was performed to obtain 13.38 g (yield 79%) of the target compound.

[0324] Mass: [(M+H)+]: 840

[0325]

[0326] [Synthesis Example 7] Synthesis of Compound 52

[0327]

[0328] Except that 2-(3''-chloro-[1,1':3',1''-terphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2, and that compound Core 1 synthesized in Preparation Example 1 was used instead of compound Core 2, the same procedure as in Synthesis Example 2 was performed to obtain 11.96 g (yield 72%) of the target compound.

[0329] Mass: [(M+H)+]: 824

[0330]

[0331] [Synthesis Example 8] Synthesis of Compound 74

[0332]

[0333] Except for using 2,4-di([1,1'-biphenyl]-4-yl)-6-chloropyrimidine instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine used in Synthesis Example 1, the same procedure as Synthesis Example 1 was performed to obtain 12.1 g (yield 68%) of the target compound.

[0334] Mass: [(M+H)+]: 747

[0335]

[0336] [Synthesis Example 9] Synthesis of Compound 84

[0337]

[0338] Except for using 4-chloro-2,6-diphenylpyrimidine instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine used in Synthesis Example 1, the same procedure as Synthesis Example 1 was performed to obtain 15.84 g (yield 63%) of the target compound.

[0339] Mass: [(M+H)+]: 671

[0340]

[0341] [Synthesis Example 10] Synthesis of Compound 93

[0342]

[0343] Except that 2,4-di([1,1'-biphenyl]-4-yl)-6-(3-chlorophenyl)pyrimidine was used instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2, and that compound Core 7 synthesized in Preparation Example 7 was used instead of compound Core 2, the same procedure as in Synthesis Example 2 was performed to obtain 17.07 g (yield 89%) of the target compound.

[0344] Mass: [(M+H)+]: 855

[0345]

[0346] [Synthesis Example 11] Synthesis of Compound 99

[0347]

[0348] Except that 4-(2'-chloro-[1,1'-biphenyl]-4-yl)-2,6-diphenylpyrimidine was used instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2, and that compound Core 3 synthesized in Preparation Example 3 was used instead of compound Core 2, the same procedure as in Synthesis Example 2 was performed to obtain 13.26 g (yield 80%) of the target compound.

[0349] Mass: [(M+H)+]: 763

[0350]

[0351] [Synthesis Example 12] Synthesis of Compound 106

[0352]

[0353] Except that 4-(2''-chloro-[1,1':2',1''-terphenyl]-2-yl)-2,6-diphenylpyrimidine was used instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2, and that compound Core 4 synthesized in Preparation Example 4 was used instead of compound Core 2, the same procedure as in Synthesis Example 2 was performed to obtain 14.23 g (yield 71%) of the target compound.

[0354] Mass: [(M+H)+]: 855

[0355]

[0356] [Synthesis Example 13] Synthesis of Compound 115

[0357]

[0358] Except that 2-(3''-chloro-[1,1':3',1''-terphenyl]-2-yl)-4,6-diphenylpyrimidine was used instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2, and that compound Core 1 synthesized in Preparation Example 1 was used instead of compound Core 2, the same procedure as in Synthesis Example 2 was performed to obtain 12.47 g (yield 75%).

[0359] Mass: [(M+H)+]: 823

[0360]

[0361] [Synthesis Example 14] Synthesis of Compound 136

[0362]

[0363] Except that 2-([1,1':3',1''-terphenyl]-4'-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine was used instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2, and that compound Core 5 synthesized in Preparation Example 5 was used instead of compound Core 2, the same procedure as in Synthesis Example 2 was performed to obtain 16.41 g (yield 79%) of the target compound.

[0364] Mass: [(M+H)+]: 824

[0365]

[0366] [Synthesis Example 15] Synthesis of Compound 140

[0367]

[0368] Except that 4-(3-chlorophenyl)-2-phenyl-6-(5'-phenyl-[1,1':2',1''-terphenyl]-3'-yl)pyrimidine was used instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2, and that compound Core 6 synthesized in Preparation Example 6 was used instead of compound Core 2, the same procedure as in Synthesis Example 2 was performed to obtain 16.2 g (yield 77%) of the target compound.

[0369] Mass: [(M+H)+]: 915

[0370]

[0371] [Synthesis Example 16] Synthesis of Compound 161

[0372]

[0373] Except that 3-(4-([1,1'-biphenyl]-4-yl)-6-(2-chlorophenyl)-1,3,5-triazin-2-yl)benzonitrile was used instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2, and that compound Core 1 synthesized in Preparation Example 1 was used instead of compound Core 2, the same procedure as in Synthesis Example 2 was performed to obtain 13.2 g (yield 66%) of the target compound.

[0374] Mass: [(M+H)+]: 773

[0375]

[0376] [Synthesis Example 17] Synthesis of Compound 162

[0377]

[0378] Except that 4-(4-(3'-chloro-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazin-2-yl)benzonitrile was used instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2, and that compound Core 1 synthesized in Preparation Example 1 was used instead of compound Core 2, the same procedure as in Synthesis Example 2 was performed to obtain 12.51 g (yield 76%) of the target compound.

[0379] Mass: [(M+H)+]: 773

[0380]

[0381] [Synthesis Example 18] Synthesis of Compound 163

[0382]

[0383] Except that 4'-(4-(2'-chloro-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile was used instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2, and that compound Core 1 synthesized in Preparation Example 1 was used instead of compound Core 2, the same procedure as in Synthesis Example 2 was performed to obtain 11.41 g (yield 70%) of the target compound.

[0384] Mass: [(M+H)+]: 849

[0385]

[0386] [Synthesis Example 19] Synthesis of Compound 164

[0387]

[0388] Except that 2-(4-([1,1'-biphenyl]-4-yl)-6-(3'-chloro-[1,1'-biphenyl]-2-yl)-1,3,5-triazin-2-yl)benzonitrile was used instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2, and that compound Core 1 synthesized in Preparation Example 1 was used instead of compound Core 2, the same procedure as in Synthesis Example 2 was performed to obtain 11.08 g (yield 68%) of the target compound.

[0389] Mass: [(M+H)+]: 849

[0390]

[0391] [Synthesis Example 20] Synthesis of Compound 165

[0392]

[0393] Except that 2-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-4'-chloro-[1,1'-biphenyl]-4-carbonitrile was used instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2, and that compound Core 1 synthesized in Preparation Example 1 was used instead of compound Core 2, the same procedure as in Synthesis Example 2 was performed to obtain 10.43 g (yield 64%) of the target compound.

[0394] Mass: [(M+H)+]: 849

[0395]

[0396] [Example 1] Fabrication of a blue organic electroluminescent device

[0397] Compound 7 synthesized in Synthesis Example 1 was purified by high-purity sublimation using a commonly known method, and then a blue organic electroluminescent device was manufactured according to the following process.

[0398] First, a glass substrate coated with a 1200 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.

[0399] On the ITO transparent electrode prepared as above, an organic electroluminescent device was manufactured by stacking 98 wt% HI + 2 wt% HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / 98 wt% BH + 2 wt% BD (20 nm) / compound 7 (5 nm) / ET-1 + Liq (1:1 weight ratio) (30 nm) / LiF (1 nm) / Al (100 nm) in that order. At this time, the structures of HI, HAT-CN6, EB, BH, BD, ET-1 and Liq used are as follows.

[0400]

[0401]

[0402] [Examples 2 to 15] Preparation of blue organic electroluminescent devices

[0403] A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compounds described in Table 1 below were used instead of compound 7 used as an electron transport auxiliary layer material in Example 1.

[0404]

[0405] [Comparative Examples 1 and 2] Manufacturing of a blue organic electroluminescent device

[0406] A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that compounds HB-1 and HB-2 were used instead of compound 7, which was used as an electron transport auxiliary layer material in Example 1. The structures of the compounds HB-1 and HB-2 used at this time are as follows.

[0407]

[0408]

[0409] [Evaluation Example 1]

[0410] For the organic electroluminescent devices manufactured in Examples 1 to 15 and Comparative Examples 1 to 2, the driving voltage, emission wavelength, and current efficiency at a current density of 10 mA / cm2 were measured, and the results are shown in Table 1 below.

[0411] Sample Electron Transport Auxiliary Layer Material Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 1 Compound 74.44576.2 Example 2 Compound 204.24616.3 Example 3 Compound 213.94607.1 Example 4 Compound 354.04616.9 Example 5 Compound 444.14596.9 Example 6 Compound 454.24586.6 Example 7 Compound 524.14576.7 Example 8 Compound 744.04616.8 Example 9 Compound 843.84627.0 Example 10 Compound 934.34596.3 Example 11 Compound 994.34596.4 Example 12 Compound 1064.44586.2 Example 13 Compound 1154.14606.5 Example 14 Compound 1364.34616.3 Example 15 Compound 1404.14576.4 Comparative Example 1 HB-14.64586.1 Comparative Example 2 HB-25.34595.6

[0412] From Table 1, it was confirmed that the organic light-emitting devices manufactured in Examples 1 to 15 had superior driving voltage, luminescence peak, and current efficiency compared to the organic light-emitting devices manufactured in Comparative Examples 1 to 2.

[0413]

[0414] [Example 16] Fabrication of a blue organic electroluminescent device

[0415] Compound 161 synthesized in Synthesis Example 16 was purified by sublimation to high purity using a commonly known method, and then a blue organic electroluminescent device was manufactured according to the following process.

[0416] First, a glass substrate coated with a 1200 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.

[0417] On the ITO transparent electrode prepared as above, an organic electroluminescent device was manufactured by stacking 98 wt% HI + 2 wt% HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / 98 wt% BH + 2 wt% BD (20 nm) / HB-1 (5 nm) / Compound 161 + Liq (1:1 weight ratio) (30 nm) / LiF (1 nm) / Al (100 nm) in that order. At this time, the structures of HI, HAT-CN6, EB, BH, BD, and Liq used are the same as those described in Example 1, and thus are omitted.

[0418]

[0419] [Examples 17 to 20] Preparation of blue organic electroluminescent devices

[0420] A blue organic electroluminescent device was manufactured in the same manner as in Example 16, except that the compounds described in Table 2 below were used instead of Compound 161, which was used as an electron transport layer material in Example 16.

[0421]

[0422] [Comparative Example 3] Fabrication of a blue organic electroluminescent device

[0423] A blue organic electroluminescent device was manufactured in the same manner as in Example 16, except that the compound ET-2 was used instead of the compound 161 used as the electron transport layer material in Example 16. The structure of ET-2 used here is as follows.

[0424]

[0425]

[0426] Sample Electron Transport Layer Material Driving Voltage (V) Peak Luminescence (nm) Current Efficiency (cd / A) Example 16 Compound 16 14.5 4 5 9 6.5 Example 17 Compound 16 24.4 4 6 16.7 Example 18 Compound 16 34.5 4 6 0 6.6 Example 19 Compound 16 44.5 4 6 26.4 Example 20 Compound 16 54.4 4 5 9 6.5 Comparative Example 3 ET-25.7 4 6 25.5

[0427] From Table 2, it was confirmed that the organic light-emitting devices manufactured in Examples 16 to 20 had superior driving voltage, luminescence peak, and current efficiency compared to the organic light-emitting device manufactured in Comparative Example 3.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] (In the above chemical formula 1, X1 and X2 are the same or different from each other, and are each independently O or S, o is an integer from 0 to 3, p, q and r are integers from 0 to 4, respectively. R1 to R4 are the same or different and each independently represents hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a hydroxyl group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of C1~C 40 Heterocycloalkyl group of C6~C 60 Aryl group of C2~C 60 Heteroaryl group of C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 selected from the group consisting of arylamine groups, or condensed with an adjacent group to form a condensed ring, Y1 to Y3 are the same or different from each other, and are each independently N or C(Ar3), provided that at least two of Y1 to Y3 are N, Ar1 to Ar3 are the same or different from each other, and each independently represents hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a hydroxyl group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of C1~C 40 Heterocycloalkyl group of C6~C 60 Aryl group of C2~C 60 Heteroaryl group of C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups; n is an integer from 0 to 5, Multiple L1s are identical or different from each other, L1 is a single bond, or C6~C 60 Arylene group and C2~C 60 is selected from the group consisting of heteroarylene 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 Ar1 to Ar3, the arylene group and heteroarylene group of the above L1, and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group and condensed ring of the above R1 to R4 are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, Amino group, hydroxyl group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of C1~C 40 Heterocycloalkyl group of C6~C 60 Aryl group of C2~C 60 Heteroaryl group of C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 (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, A compound wherein the above X1 and X2-containing ring moieties are selected from the group consisting of the following moieties Mo1-1 to Mo1-4: (In the above moieties Mo1-1 to Mo1-4, o, p, q, r and R1 to R4 are each as defined in Article 1).

3. In paragraph 1, A compound wherein the above Y1 to Y3-containing ring is selected from the group consisting of the following moieties Az1-1 to Az1-3: (In the above moieties Az1-1 to Az1-3, Ar1 to Ar3 are each as defined in Article 1).

4. In paragraph 1, Ar1 and Ar2 are the same or different from each other, and are each independently C6~C 60 Aryl group and C2~C 60 A compound selected from the group consisting of heteroaryl groups.

5. In paragraph 1, A compound wherein Ar1 and Ar2 are the same or different and are each independently selected from the group consisting of the following substituents S1-1 to S1-21: (In the above substituents S1-1 to S1-21, a is an integer from 0 to 5, b is an integer from 0 to 4, c is an integer from 0 to 7, d is an integer from 0 to 6, e is an integer from 0 to 3, f is an integer between 0 and 2, g is an integer from 0 to 9, h is an integer from 0 to 11, Multiple R's are identical or different from each other, R is hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of C1~C 40 Heterocycloalkyl group of C6~C 60 Aryl group of C2~C 60 Heteroaryl group of C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 (selected from the group consisting of arylamine groups).

6. In paragraph 1, wherein the above L1 is a single bond or a compound of the following linker group L1-1: (In the above linker L1-1, i is an integer from 0 to 4, Multiple R's are identical or different from each other, R is hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of C1~C 40 Heterocycloalkyl group of C6~C 60 Aryl group of C2~C 60 Heteroaryl group of C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 (selected from the group consisting of arylamine groups).

7. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 2 to 5: [Chemical formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] (In the above chemical formulas 2 to 5, X1, X2, o, p, q, r, R1 to R4, Y1, Y2, Y3, Ar1, Ar2, n, L1 are each as defined in Article 1).

8. In paragraph 1, The compound represented by the chemical formula 1 above is a compound represented by any one of the following chemical formulas 6 to 14: [Chemical formula 6] [Chemical formula 7] [Chemical formula 8] [Chemical formula 9] [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 16] [Chemical Formula 17] (In the above chemical formulas 6 to 17, X1, X2, o, p, q, r, R1 to R4, Ar1, Ar2, n, L1 are each as defined in Article 1).

9. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 18 to 20: [Chemical Formula 18] [Chemical Formula 19] [Chemical formula 20] (In the above chemical formulas 18 to 20, X1, X2, o, p, q, r, R1 to R4, Ar1, Ar2, n are each as defined in Article 1, i is an integer from 0 to 4, Multiple R's are identical or different from each other, R is hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of C1~C 40 Heterocycloalkyl group of C6~C 60 Aryl group of C2~C 60 Heteroaryl group of C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 (selected from the group consisting of arylamine groups).

10. In paragraph 1, The compound represented by the chemical formula 1 above is a compound represented by any one of the following chemical formulas 21 to 32: [Chemical Formula 21] [Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 24] [Chemical Formula 25] [Chemical Formula 26] [Chemical Formula 27] [Chemical formula 28] [Chemical Formula 29] [Chemical formula 30] [Chemical Formula 31] [Chemical formula 32] (In the above chemical formulas 21 to 32, o, p, q, r, R1 to R4, Ar1, Ar2, and n are each as defined in Article 1, i is an integer from 0 to 4, Multiple R's are identical or different from each other, R is hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of C1~C 40 Heterocycloalkyl group of C6~C 60 Aryl group of C2~C 60 Heteroaryl group of C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 (selected from the group consisting of arylamine groups).

11. In paragraph 1, The compound represented by the chemical formula 1 above is a compound represented by any one of the following chemical formulas 33 to 59: [Chemical Formula 33] [Chemical Formula 34] [Chemical Formula 35] [Chemical formula 36] [Chemical Formula 37] [Chemical formula 38] [Chemical Formula 39] [Chemical formula 40] [Chemical Formula 41] [Chemical formula 42] [Chemical formula 43] [Chemical Formula 44] [Chemical Formula 45] [Chemical Formula 46] [Chemical Formula 47] [Chemical formula 48] [Chemical Formula 49] [Chemical formula 50] [Chemical Formula 51] [Chemical formula 52] [Chemical formula 53] [Chemical Formula 54] [Chemical formula 55] [Chemical formula 56] [Chemical formula 57] [Chemical formula 58] [Chemical formula 59] (In the above chemical formulas 33 to 59, R1 to R4, Ar1, Ar2, and n are each as defined in Article 1, i is an integer from 0 to 4, Multiple R's are identical or different from each other, R is hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of C1~C 40 Heterocycloalkyl group of C6~C 60 Aryl group of C2~C 60 Heteroaryl group of C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, Ring Cy1 is selected from the group consisting of 6- to 18-membered condensed aromatic rings and 5- to 18-membered condensed heteroaromatic rings.

12. In paragraph 1, The compound represented by the above chemical formula 1 is a compound selected from the group consisting of compounds 1 to 165 below: .

13. Anode; cathode; comprising at least one organic layer interposed between the anode and cathode, An organic electroluminescent device, wherein at least one of the organic layers of one or more layers comprises an organic compound according to any one of claims 1 to 12.

14. In paragraph 13, An organic electroluminescent device, wherein the organic layer containing the organic compound is a light-emitting layer, an electron transport layer, or an electron transport auxiliary layer.

Images