KR20260009242A - Organic compound and organic electroluminescent device comprising the same - Google Patents

Abstract

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

Description

Organic compound and organic electroluminescent device comprising the same {ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME}

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 characteristics such as electron injection and transport ability, luminescence ability, electrical stability, and thermal stability, and an organic electroluminescent device having improved characteristics such as luminescence efficiency, driving voltage, and lifespan by including the same in one or more organic layers.

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.

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.

To date, NPB, BCP, Alq ₃ , etc., expressed by the following chemical formula, 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. To date, CBP has shown excellent properties as a phosphorescent host material.

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.

The present invention aims to provide a novel compound having improved electron injection and transport capabilities and excellent thermal stability, which can be used as an organic layer material of an organic electroluminescent device, specifically, an electron transport layer material or an electron transport auxiliary layer material.

In addition, another object of the present invention is to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, and improved lifespan characteristics, including the novel compound described above.

To achieve the above-mentioned purpose, the present invention provides a compound represented by the following chemical formula 1:

(In the above chemical formula 1,

X ₁ to X ₃ are the same or different from each other, and are each independently N or C(Ar ₂ ), provided that at least one of X ₁ to X ₃ is N;

Ar ₁ and Ar ₂ are the same or different from each other, and each independently represent hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C Selected from the group consisting of an arylborone group of ₆₀ , an arylphosphine group of C ₆ to C ₆₀ , an arylphosphine oxide group of C ₆ to C ₆₀ , and an arylamine group of C ₆ to C ₆₀ ;

L ₁ and L ₂ are the same or different from each other, and each independently represents a single bond or is selected from the group consisting of an arylene group having C ₆ to C ₂₄ and a heteroarylene group having 5 to 24 nuclear atoms;

Ring Cy1 is present or absent, and when ring Cy1 is present, ring Cy1 is a six-membered fused aromatic ring;

a and b are integers from 0 to 2, respectively,

n and m are integers from 0 to 5, respectively.

However, if a+b≥1, and in this case a+b=1, then n+m≥1, and if a+b≥2, then n+m≥0;

Multiple R ₁ 's are the same or different from each other,

Multiple R ₂ are the same or different,

R ₁ and R ₂ are the same or different, and are each independently selected from the group consisting of an aryl group having C ₆ to C ₆₀ and a heteroaryl group having 5 to 50 nuclear atoms, or are condensed with an adjacent group to form a condensed ring;

c, e and f are integers from 0 to 5, respectively.

d is an integer from 0 to 4,

Multiple R ₃ 's are the same or different from each other,

Multiple R ₄ 's are the same or different,

Multiple R ₅ 's are the same or different from each other,

Multiple R ₆ are the same or different,

R ₃ to R ₆ are the same or different from each other, and each independently represent hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C Selected from the group consisting of an arylboron group of ₆₀ , an arylphosphine group of C ₆ to C ₆₀ , an arylphosphine oxide group of C ₆ to C ₆₀ , and an arylamine group of C ₆ to C ₆₀ , or condensed with an adjacent group to form a condensed ring;

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 Ar 1 and Ar 2, the arylene group and heteroarylene group of the above L ₁ and L ₂ , the aryl group, heteroaryl group and condensed ring of the above R _{1 and} R _{2 ,} 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, The arylphosphine oxide group, the arylamine group and the condensed ring are each independently selected from the group _consisting of deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C ₁ ~C ₄₀ alkyl group, C ₂ ~C ₄₀ alkenyl group, C ₂ ~C ₄₀ alkynyl group, C ₃ ~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~C ₄₀ alkyloxy group, C ₆ ~C ₆₀ aryloxy group, C ₁ ~C ₄₀ alkylsilyl group, C ₆ ~C ₆₀ arylsilyl group, C ₁ ~C ₄₀ alkylboron group, C ₆ ~C ₆₀ (Substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl boron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group, or the substituents are condensed with each other to form a condensed ring, and in this case, when there are multiple substituents, they are the same or different from each other.)

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.

For example, the organic layer including the organic compound may be an electron transport layer, an electron transport auxiliary layer, or both.

The compound of the present invention can be used as an organic layer material of an organic electroluminescent device because it has excellent electron transport and injection capabilities, luminescence, heat resistance, electrochemical stability, etc. In particular, when the compound of the present invention is used as at least one of an electron transport layer material and an electron transport auxiliary layer material, an organic electroluminescent device having superior luminescence performance, low driving voltage, high efficiency, fast mobility, and long lifespan characteristics compared to conventional materials can be manufactured, and further, a full-color display panel with improved performance and lifespan can also be manufactured.

FIG. 1 is a cross-sectional view schematically showing an organic electroluminescent device according to a first embodiment of the present invention.
Figure 2 is a cross-sectional view schematically showing an organic electroluminescent device according to a second embodiment of the present invention.
FIG. 3 is a cross-sectional view schematically showing an organic electroluminescent device according to a third embodiment of the present invention.

Hereinafter, the present invention will be described.

<New organic compounds>

The compound according to the present invention has a structure in which a phenyl-substituted silane moiety and a multi-aryl group-containing moiety are bonded directly or through a linker group to a nitrogen-containing heteroaromatic ring moiety, and is represented by the above chemical formula 1. Such a compound is excellent in heat resistance, carrier transport ability (particularly, electron injection and transport ability), luminescence ability, electrochemical stability, etc., and can implement the characteristics of an organic electroluminescent device, such as high efficiency, long life, and low driving voltage characteristics of the device.

Specifically, in the organic compound represented by chemical formula 1 according to the present invention, the phenyl-substituted silane moiety is a moiety in which all hydrogens of silane (SiH ₄ ) are replaced with phenyl groups, wherein the phenyl groups may also be substituted or unsubstituted with various substituents such as deuterium (D), a cyano group (-CN), an alkyl group (e.g., methyl, etc.), and an aryl group (e.g., phenyl, etc.). Such a phenyl-substituted silane moiety has excellent electron accepting capacity. In addition, since the phenyl-substituted silane moiety contains silicon (Si) instead of carbon (C), in addition to the electron donor properties of the phenyl group portion, it has high electron conductivity and thus excellent electron transport properties. Therefore, when the compound according to the present invention is applied as a material of an electron transport layer or an electron transport auxiliary layer of an organic electroluminescent device, electrons can be smoothly transferred from the cathode (or electron injection layer) to the light-emitting layer, and as a result, the driving voltage of the device can be lowered, and high efficiency and long life characteristics can be realized.

In addition, the phenyl-substituted silane moiety is a bulky substituent, and the conjugation is broken. Therefore, the compound of the present invention has a wide energy band gap (Eg) and a high excited triplet energy level, and thus has excellent electron transport ability not only in fluorescent materials but also in phosphorescent materials.

In addition, in the compound of the present invention, the multi-aryl group-containing moiety contains two or more phenyl groups, for example, a moiety composed of three or more phenyl groups such as terphenyl, uaterphenyl, quinquephenyl, diphenyl-terphenyl, or a moiety composed of two or more phenyl groups such as biphenyl-naphthalene, biphenyl-dibenzofuran, and the like, and another aryl group or heteroaryl group such as a naphthyl group, a dibenzofuran group, or a dibenzothiophene group. These multi-aryl group-containing moieties are arranged opposite to phenyl-substituted silane moieties with a nitrogen-containing heteroaromatic ring moiety as the center. Accordingly, the compound of the present invention has excellent thermal stability because the glass transition temperature is higher relative to the molecular weight compared to the case where silane moieties are arranged on both sides with a nitrogen-containing heteroaromatic ring moiety as the center. In addition, the compound of the present invention can control electron mobility, thereby maintaining the charge balance of holes and electrons, thereby increasing the luminescence efficiency of an organic electroluminescent device.

As described above, the compound represented by the chemical formula 1 of the present invention has excellent electron injection and transport ability, thermal stability, electrochemical stability, carrier transport ability, luminescence ability, etc., and thus can be used as an organic layer material of an organic electroluminescent device, specifically, a luminescent layer material, an electron transport layer/injection layer material, an electron transport auxiliary layer material, a life-span improvement layer material, a luminescent auxiliary layer material, and more specifically, an electron transport layer material, an electron transport auxiliary layer material. In addition, an organic electroluminescent device including the compound of the chemical formula 1 can have greatly improved performance and life-span characteristics, and a full-color organic light-emitting panel to which such an organic electroluminescent device is applied can also have its performance maximized.

The organic compound represented by chemical formula 1 according to the present invention comprises a phenyl-substituted silane moiety ( ) on one side of a nitrogen-containing heteroaromatic ring moiety ( ) are bonded directly or through a linker group (L ₁ ). At this time, it can have various forms depending on the bonding position between the phenyl-substituted silane moiety and the nitrogen-containing heteroaromatic ring moiety.

For example, the organic compound represented by the above chemical formula 1 may be a compound represented by any one of the following chemical formulas 2 to 4. However, the present invention is not limited thereto.

In the above chemical formulas 2 to 4,

X ₁ to X ₃ , Ar ₁ , L ₁ , L ₂ , ring Cy1, a, b, n, m, c, d, e, f and R ₁ to R ₆ are each as defined in the above chemical formula 1.

In addition, in the compound represented by chemical formula 1 according to the present invention, the nitrogen-containing heteroaromatic ring moiety (X ₁ to X ₃ -containing ring moiety) contains 1 to 3 nitrogens (N), and is an electron withdrawing group (EWG) with excellent electron transport ability. In this nitrogen-containing heteroaromatic ring moiety, X ₁ to X ₃ are the same as or different from each other, and are each independently N or C(Ar ₂ ), provided that at least one of X ₁ to X ₃ is 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.

For example, the above X ₁ to X ₃ -containing ring moiety ( ) may be selected from the group consisting of the following moieties Az1-1 to Az1-7.

In the above moieties Az1-1 to Az1-7,

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

Ar ₁ and Ar ₂ are each as defined in the above chemical formula 1.

In the above-mentioned nitrogen-containing heteroaromatic ring moiety (X ₁ to X ₃ -containing ring), Ar ₁ and Ar ₂ are the same as 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 (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), C ₁ to C ₄₀ alkyl group, _{C 2 to} C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to _C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C 6 ~ C ₆₀ arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group and C ₆ ~ C ₆₀ arylamine group, and specifically, each independently selected from the group consisting of hydrogen, deuterium (D), C ₁ ~ C ₂₀ alkyl group, C ₆ ~ C ₃₀ aryl group, C ₂ ~ C ₃₀ heteroaryl group, C ₆ ~ C ₃₀ arylphosphine oxide group and C ₆ ~ C ₃₀ arylamine group, _and more specifically, each independently selected from the group consisting of hydrogen, deuterium (D), phenyl group, biphenyl group, It may be selected from the group consisting of a terphenyl group, a naphthyl group, a triphenylenyl group, a phenanthryl group, a fluorenyl group, anthracenyl group, anthryl group, a pyrenyl group, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, a dibenzofuran group, a dibenzothiophene group, a phenanthrolinyl group, and a carbazolyl group.

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 Ar 1 and Ar 2 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), C ₁ ~C ₄₀ alkyl group, C ₂ ~C ₄₀ alkenyl group, C ₂ ~C ₄₀ alkynyl group, C ₃ ~C ₄₀ cycloalkyl group, and 3 to 40 nuclear atoms. A heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylborone group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group, each independently selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), It may be _{substituted or unsubstituted} with one or more substituents selected from the group consisting of an amino group (-NH ₂ ), a hydroxy group (-OH), a C ₁ to C ₂₀ alkyl group, a C 6 to C ₃₀ aryl group, a C ₂ to C ₃₀ heteroaryl group, a C ₆ to C ₃₀ arylphosphine oxide group, and a C 6 to C 30 arylamine group, or the substituents may be condensed with each other to form a condensed ring. If there are multiple substituents, they may be the same or different.

For example, Ar ₁ and Ar ₂ are the same as or different from each other, and can be independently selected from the group consisting of hydrogen, a C ₆ to C ₃₀ aryl group, and a C ₂ to C ₃₀ heteroaryl group, and the aryl group and heteroaryl group of Ar ₁ and Ar ₂ can be independently substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, _etc. ), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), _{hydroxy group (-OH), a C 1 to} C ₂₀ alkyl group, a C ₆ to C ₃₀ aryl group, a C ₂ to C ₃₀ heteroaryl group, a C ₆ to C 30 arylphosphine oxide group, and a C 6 to C ₃₀ arylamine group. If there are multiple substituents, they may be the same or different.

In another example, Ar ₁ and Ar ₂ may be the same as or different from each other, and each independently be hydrogen, or may be selected from the group consisting of the following substituents S1-1 to S1-10, but are not limited thereto.

In the above substituents S1-1 to S1-10,

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

g, g1 and g2 are each integers from 0 to 5, specifically, each integer from 0 to 3,

h, h1, h2 are each integers from 0 to 4, specifically, they are each integers from 0 to 2,

i is an integer from 0 to 7, specifically an integer from 0 to 4, and more specifically an integer from 0 to 2,

j is an integer from 0 to 6, specifically an integer from 0 to 3,

k is an integer from 0 to 9, specifically an integer from 0 to 4, and more specifically an integer from 0 to 2,

l is an integer from 0 to 3,

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

R is hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C It is selected from the group consisting of an alkylboron group of ₄₀ , an arylborone group of C ₆ ~C ₆₀ , an arylphosphine group of C ₆ ~C ₆₀ , an arylphosphine oxide group of C ₆ ~C ₆₀ and an arylamine group of C ₆ ~C ₆₀ , and specifically, it can be selected from the group consisting of hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH _{2 ), hydroxy group (-OH), an alkyl group of C 1 ~} C ₂₀ , an aryl group of C ₆ ~C ₃₀ , a heteroaryl group of C ₂ ~C ₃₀ , an arylphosphine oxide group of C 6 ~C ₃₀ and an arylamine group of C ₆ ~C ₃₀ , and more specifically, hydrogen, deuterium (D), It can be selected from the group consisting of halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, adamantyl group, norbornyl, phenyl group, biphenyl group, terphenyl group, naphthyl group, dibenzofuran group, dibenzothiophene group and fluorene group,

Y ₁ is selected from the group consisting of O, S, C(Ar ₃ )(Ar ₄ ), Si(Ar ₅ )(Ar ₆ ) and N(Ar ₇ ),

Ar ₃ to Ar ₇ are the same or different from each other, and each independently represent hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, _{C 2 to} C ₄₀ alkynyl group, C 3 to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C 6 ~ C ₆₀ arylphosphine oxide group and C ₆ ~ C ₆₀ arylamine group, or condensed with adjacent groups (e.g., Ar ₃ -Ar ₄ , Ar ₅ -Ar ₆ , Ar ₃ -R, Ar ₅ -R, Ar ₇ -R) to form a condensed ring, and specifically, each independently hydrogen, deuterium (D ₎ , halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), C ₁ ~ C ₂₀ alkyl group, C ₆ ~ C ₃₀ aryl group, C It is selected from the group consisting of a heteroaryl group having ₂ to C ₃₀ , an arylphosphine oxide group having ₆ to C ₃₀ , and an arylamine group having ₆ to C ₃₀ , or can be condensed with an adjacent group (e.g., Ar ₃ -Ar ₄ , Ar ₅ -Ar ₆ , Ar ₃ -R, Ar ₅ -R, Ar ₇ -R) to form a condensed ring. Here, the condensed ring may be at least one selected from the group consisting of a C ₃ to C ₆₀ condensed aliphatic ring (specifically, a C ₃ to C ₃₀ condensed aliphatic ring), a C ₆ to C ₆₀ condensed aromatic ring (specifically, a C ₆ to C ₃₀ condensed aromatic ring), a 5- to 60-membered condensed heteroaromatic ring containing a heteroatom such as N, O or S (specifically, a 5- to 30-membered condensed heteroaromatic ring), a C ₃ to C ₆₀ spiro ring, and combinations thereof.

In addition, in the compound represented by the chemical formula 1 according to the present invention, L ₁ and L ₂ are the same as or different from each other, and are each independently a single bond (direct bond) or are selected from the group consisting of an arylene group of C ₆ to C ₂₄ and a heteroarylene group having 5 to 24 nuclear atoms, and specifically, may be a single bond (direct bond) or may be selected from the group consisting of an arylene group of C ₆ to C ₁₈ and a heteroarylene group having 3 to 18 nuclear atoms.

At this time, the arylene group and heteroarylene group of L ₁ and L ₂ are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), C ₁ ~C ₄₀ alkyl group, C ₂ ~C ₄₀ alkenyl group, C ₂ ~C ₄₀ alkynyl group, C ₃ ~C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~C ₄₀ alkyloxy group, C ₆ ~C ₆₀ aryloxy group, C ₁ ~C ₄₀ Substituted _{or unsubstituted with at least one substituent selected from the group consisting of an alkylsilyl group, an arylsilyl group having a carbon number of 6 to 60, an alkylboron group having a carbon number of 1 to 40 , an arylboron group having a carbon} number of ₆ to ₆₀ , an arylphosphine group having a carbon number of 6 to 60, an arylphosphine oxide group having a carbon number of ₆ to ₆₀ , and an arylamine group having a carbon number of 6 to 60, and specifically, each selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), an alkyl group having a carbon number of ₁ to ₁₂ , an aryl group having a carbon number of ₆ to ₁₈ , a heteroaryl group having a carbon number of 5 to 18, and an arylamine group having a carbon number of ₆ to ₁₈ It may be substituted or unsubstituted with one or more substituents, or the substituents may be condensed with each other to form a condensed ring. If there are multiple substituents, they may be the same or different.

In one embodiment, L ₁ and L ₂ are the same as or different from each other, and each independently represents a single bond or may be selected from the group consisting of a phenylene group, a biphenylene group, a terphenylene group, a divalent naphthalene group, a divalent phenanthrene group, a divalent triphenylene group, a divalent carbazole group, a divalent dibenzofuran group, a divalent dibenzothiophene group, a divalent fluorene group, and combinations thereof. Here, the phenylene group, the biphenylene group, the terphenylene group, the divalent naphthalene group, the divalent phenanthrene group, the divalent triphenylene group, the divalent carbazole group, the divalent dibenzofuran group, the divalent dibenzothiophene group, and the divalent fluorene group may be independently substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), C ₁ to C ₁₂ alkyl group, C ₆ to C ₁₀ aryl group, and heteroaryl group having 5 to 10 nuclear atoms.

In another example, L ₁ and L ₂ may be the same or different, and each independently be a single bond, or may be selected from the group consisting of linker groups L1-1 to L1-4, but are not limited thereto.

In the above linker groups L1-1 to L1-4,

* indicates the part that is combined with chemical formula 1.

o is an integer from 1 to 4,

p1 is an integer from 0 to 4,

p2 and p3 are integers from 0 to 6, respectively,

p4 is an integer from 0 to 7,

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

R is hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C It is selected from the group consisting of an alkylboron group of ₄₀ , an arylborone group of C ₆ to C ₆₀ , an arylphosphine group of C _{6 to} C ₆₀ , an arylphosphine oxide group of C ₆ to C ₆₀ , and an arylamine group of C 6 to C ₆₀ , and specifically, it can be selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I _, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), an alkyl group of C ₁ to C ₂₀ , an aryl group of C 6 to C ₃₀ , a heteroaryl group having 5 to 30 nuclear atoms, an arylphosphine oxide group of C ₆ to C ₃₀ , and an arylamine group of C ₆ to C ₃₀ ,

Z ₁ is selected from the group consisting of O, S, C(Ar ₈ )(Ar ₉ ), Si(Ar ₁₀ )(Ar ₁₁ ) and N(Ar ₁₂ ),

Ar ₈ to Ar ₁₂ are the same or different from each other, and each independently represent hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), C ₁ ~C ₄₀ alkyl group, C ₂ ~C ₄₀ alkenyl group, C ₂ ~C ₄₀ alkynyl group, C ₃ ~C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~C ₄₀ alkyloxy group, C ₆ ~C ₆₀ aryloxy group, C ₁ ~C ₄₀ alkylsilyl group, C ₆ ~C ₆₀ arylsilyl group, C ₁ ~C ₄₀ alkylboron group, C ₆ ~C ₆₀ arylboron group, C ₆ ~C ₆₀ arylphosphine group, C ₆ ~C ₆₀ arylphosphine oxide group and C ₆ ~C ₆₀ arylamine group, or condensed with adjacent groups (e.g., Ar ₈ -Ar ₉ , Ar ₁₀ -Ar ₁₁ , Ar ₈ -R, Ar ₁₀ -R, Ar ₁₂ -R) to form a condensed ring, and specifically, each independently hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), C ₁ ~C ₂₀ alkyl group, C ₆ ~C ₃₀ It is selected from the group consisting of an aryl group of C ₂ ~C ₃₀ , a heteroaryl group of C ₆ ~C ₃₀ , an arylphosphine oxide group of C ₆ ~C 30, and an arylamine group of C 6 ~C ₃₀ , or can form a condensed ring by condensation with an adjacent group (e.g., Ar ₈ -Ar ₉ , Ar ₁₀ -Ar ₁₁ , Ar ₈ -R, Ar ₁₀ -R, Ar ₁₂ -R). Here, the condensed ring may be at least one selected from the group consisting of a C ₃ to C ₆₀ condensed aliphatic ring (specifically, a C ₃ to C ₃₀ condensed aliphatic ring), a C ₆ to C ₆₀ condensed aromatic ring (specifically, a C ₆ to C ₃₀ condensed aromatic ring), a 5- to 60-membered condensed heteroaromatic ring containing a heteroatom such as N, O or S (specifically, a 5- to 30-membered condensed heteroaromatic ring), a C ₃ to C ₆₀ spiro ring, and combinations thereof.

According to another example, L ₁ is a single bond; L ₂ is a single bond or may be selected from the group consisting of linker groups L1-1 to L1-4.

In addition, in the compound represented by chemical formula 1 according to the present invention, ring Cy1 is present or absent, and when ring Cy1 is present, ring Cy1 is a 6-membered fused aromatic ring. Here, the 6-membered fused aromatic ring is an aromatic ring fused to a benzene ring.

Depending on the presence or absence of the ring Cy1, the organic compound represented by the above chemical formula 1 may be a compound represented by any one of the following chemical formulas 5 to 10, but is not limited thereto.

In the above chemical formulas 5 to 10,

X ₁ to X ₃ , Ar ₁ , L ₁ , L ₂ , a, b, n, m, R ₁ , R ₂ , c, d, e, f and R _{3 to R 6 are} each as defined in the above chemical formula 1.

In addition, in the compound represented by the chemical formula 1 according to the present invention, a and b are each integers from 0 to 2, and n and m are each integers from 0 to 5. However, a+b≥1, and in this case, when a+b=1, n+m≥1, and in the case of a+b≥2, n+m≥0. Here, when a is 0, R ₁ -substituted phenyl group (where hydrogen is a substituent) ) means non-substituted, and when a is 1 or 2, it means that hydrogen is substituted by an R ₁ -substituted phenyl group which is a substituent. On the other hand, when b is 0, it means that hydrogen is substituted by an R ₂ -substituted phenyl group which is a substituent. ) means that hydrogen is not substituted with a substituent R ₂ -substituted phenyl group, and when b is 1 or 2, it means that hydrogen is substituted with a substituent R 2 -substituted phenyl group. On the other hand, when n is 0, it means that hydrogen is not substituted with a substituent R ₁ , and when n is an integer from 1 to 5, it means that hydrogen is substituted with a substituent R ₁ . On the other hand, when m is 0, it means that hydrogen is not substituted with a substituent R ₂ , and when m is an integer from 1 to 5, it means that hydrogen is substituted with a substituent R ₂ . At this time, a plurality of R ₁ are the same or different from each other, and a plurality of R ₂ are the same or different from each other.

R ₁ and R ₂ are the same as or different from each other, and are each independently selected from the group consisting of an aryl group having C ₆ to C ₆₀ and a heteroaryl group having 5 to 60 nuclear atoms, or are condensed with an adjacent group (e.g., R ₁ -R ₁ , R ₂ -R ₂ , R ₁ -L ₂ , R ₂ -L ₂ ) to form a condensed ring, specifically, are aryl groups having C ₆ to C ₃₀ , or can be condensed with an adjacent group (e.g., R ₁ -R ₁ , R ₂ -R ₂ , R ₁ -L ₂ , R ₂ -L ₂ ) to form a condensed ring. Here, the condensed ring may be at least one selected from the group consisting of a C ₃ to C ₆₀ condensed aliphatic ring (specifically, a C ₃ to C ₃₀ condensed aliphatic ring), a C ₆ to C ₆₀ condensed aromatic ring (specifically, a C ₆ to C ₃₀ condensed aromatic ring), a 5- to 60-membered condensed heteroaromatic ring containing a heteroatom such as N, O or S (specifically, a 5- to 30-membered condensed heteroaromatic ring), a C ₃ to C ₆₀ spiro ring, and combinations thereof.

At this time, the aryl group, heteroaryl group and condensed ring of R ₁ and R ₂ are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), C ₁ ~C ₄₀ alkyl group, C ₂ ~C ₄₀ alkenyl group, C ₂ ~C ₄₀ alkynyl group, C ₃ ~C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~C ₄₀ alkyloxy group, C ₆ ~C ₆₀ aryloxy group, C ₁ ~C ₄₀ Substituted _{or unsubstituted with at least one substituent selected from the group consisting of an alkylsilyl group, an arylsilyl group having a carbon number of 6 to 60, an alkylboron group having a carbon number of 1 to 40 , an arylboron group having a carbon} number of ₆ to ₆₀ , an arylphosphine group having a carbon number of 6 to 60, an arylphosphine oxide group having a carbon number of ₆ to ₆₀ , and an arylamine group having a carbon number of 6 to 60, and specifically, each selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), an alkyl group having a carbon number of ₁ to ₁₂ , an aryl group having a carbon number of ₆ to ₁₈ , a heteroaryl group having a carbon number of 5 to 18, and an arylamine group having a carbon number of ₆ to ₁₈ It may be substituted or unsubstituted with one or more substituents, or the substituents may be condensed with each other to form a condensed ring. If there are multiple substituents, they may be the same or different.

In one embodiment, R ₁ and R ₂ are the same as or different from each other, and are each independently selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a dibenzothiophenyl group, and a dibenzofuranyl group, or may be condensed with an adjacent group (e.g., R ₁ -R ₁ , R ₂ -R ₂ ) to form a condensed ring (e.g., a dibenzothiophene ring, a dibenzofuran ring, a fluorene ring, etc.). At this time, the phenyl group, biphenyl group, terphenyl group, naphthyl group and condensed ring may be independently substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), C ₁ to C ₁₂ alkyl group, C ₆ to C ₁₀ aryl group and heteroaryl group having 5 to 10 nuclear atoms.

According to the above a and b, in the chemical formula 1 The moiety may be selected from the group consisting of the following moieties Mo1-1 to Mo1-24, but is not limited thereto.

In the above moieties Mo1-1 to Mo1-24,

* indicates the part that is combined with chemical formula 1.

n and m are each as defined in the above chemical formula 1,

Plural n's are the same or different from each other,

Plural m are the same or different,

n1 is an integer from 1 to 4,

m1 is an integer from 1 to 5,

q1 to q4 are integers from 0 to 5, respectively,

q5 is an integer from 0 to 7,

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

R is hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C It is selected from the group consisting of an alkylboron group of ₄₀ , an arylborone group of C ₆ to C ₆₀ , an arylphosphine group of C _{6 to} C ₆₀ , an arylphosphine oxide group of C ₆ to C ₆₀ , and an arylamine group of C 6 to C ₆₀ , and specifically, it can be selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I _, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), an alkyl group of C ₁ to C ₂₀ , an aryl group of C 6 to C ₃₀ , a heteroaryl group having 5 to 30 nuclear atoms, an arylphosphine oxide group of C ₆ to C ₃₀ , and an arylamine group of C ₆ to C ₃₀ ,

W is selected from the group consisting of O, S, C(Ar ₁₃ )(Ar ₁₄ ), Si(Ar ₁₅ )(Ar ₁₆ ) and N(Ar ₁₇ ),

Ar ₁₃ to Ar ₁₇ 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 (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ ~C ₆₀ arylsilyl group, C ₁ ~C ₄₀ alkylboron group, C ₆ ~C ₆₀ arylboron group, C ₆ ~C ₆₀ arylphosphine group, C ₆ ~C ₆₀ arylphosphine oxide group and C ₆ ~C ₆₀ arylamine group, or condensed with adjacent groups (e.g., Ar ₁₃ -Ar ₁₄ , Ar ₁₅ -Ar ₁₆ , Ar ₁₃ -R, Ar ₁₅ -R, Ar ₁₇ -R) to form a condensed ring, and specifically, each independently hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), C ₁ ~C ₂₀ alkyl group, C ₆ ~C It is selected from the group consisting of an aryl group of ₃₀ , a heteroaryl group of C ₂ to C ₃₀ , an arylphosphine oxide group of C ₆ to C ₃₀ , and an arylamine group of C ₆ to C ₃₀ , or can form a condensed ring by condensation with an adjacent group (e.g., Ar ₁₃ -Ar ₁₄ , Ar ₁₅ -Ar ₁₆ , Ar ₁₃ -R, Ar ₁₅ -R, Ar ₁₇ -R). Here, the condensed ring may be at least one selected from the group consisting of a C ₃ to C ₆₀ condensed aliphatic ring (specifically, a C ₃ to C ₃₀ condensed aliphatic ring), a C ₆ to C ₆₀ condensed aromatic ring (specifically, a C ₆ to C ₃₀ condensed aromatic ring), a 5- to 60-membered condensed heteroaromatic ring containing a heteroatom such as N, O or S (specifically, a 5- to 30-membered condensed heteroaromatic ring), a C ₃ to C ₆₀ spiro ring, and combinations thereof.

As an example, the above The moiety may be selected from the group consisting of the following moieties Mo2-1 to Mo2-100, but is not limited thereto.

In the above moieties Mo2-1 to Mo2-100,

* indicates a site that is combined with chemical formula 1,

W is selected from the group consisting of O, S, C(Ar ₁₃ )(Ar ₁₄ ), Si(Ar ₁₅ )(Ar ₁₆ ) and N(Ar ₁₇ ),

Ar ₁₃ to Ar ₁₇ 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 (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ ~C ₆₀ arylsilyl group, C ₁ ~C ₄₀ alkylboron group, C ₆ ~C ₆₀ arylboron group, C ₆ ~C ₆₀ arylphosphine group, C ₆ ~C ₆₀ arylphosphine oxide group and C ₆ ~C ₆₀ arylamine group, or is selected from the group consisting of adjacent groups (e.g., Ar ₁₃ -Ar ₁₄ , Ar ₁₅ -Ar ₁₆ , Ar ₁₃ -R, Ar ₁₅ -R, Ar ₁₇ -R) to form a condensed ring, and specifically, each independently hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), C ₁ ~C ₂₀ alkyl group, C ₆ ~C It is selected from the group consisting of an aryl group of ₃₀ , a heteroaryl group of C ₂ to C ₃₀ , an arylphosphine oxide group of C ₆ to C ₃₀ , and an arylamine group of C ₆ to C ₃₀ , or can form a condensed ring by condensation with an adjacent group (e.g., Ar ₁₃ -Ar ₁₄ , Ar ₁₅ -Ar ₁₆ , Ar ₁₃ -R, Ar ₁₅ -R, Ar ₁₇ -R). Here, the condensed ring may be at least one selected from the group consisting of a C ₃ to C ₆₀ condensed aliphatic ring (specifically, a C ₃ to C ₃₀ condensed aliphatic ring), a C ₆ to C ₆₀ condensed aromatic ring (specifically, a C ₆ to C ₃₀ condensed aromatic ring), a 5- to 60-membered condensed heteroaromatic ring containing a heteroatom such as N, O or S (specifically, a 5- to 30-membered condensed heteroaromatic ring), a C ₃ to C ₆₀ spiro ring, and combinations thereof.

In addition, in the compound represented by chemical formula 1 according to the present invention, c, e and f are each an integer from 0 to 5, and d is an integer from 0 to 4. Here, when c is 0, it means that hydrogen is not substituted with a substituent R ₃ , and when c is an integer from 1 to 5, it means that hydrogen is substituted with a substituent R ₃ . On the other hand, when d is 0, it means that hydrogen is not substituted with a substituent R ₄ , and when d is an integer from 1 to 4, it means that hydrogen is substituted with a substituent R ₄ . On the other hand, when e is 0, it means that hydrogen is not substituted with a substituent R ₅ , and when e is an integer from 1 to 5, it means that hydrogen is substituted with a substituent R ₅ . Meanwhile, when f is 0, it means that hydrogen is not substituted with the substituent R ₆ , and when f is an integer from 1 to 5, it means that hydrogen is substituted with the substituent R ₆ . At this time, a plurality of R _3s are the same or different from each other, a plurality of R _4s are the same or different from each other, a plurality of R _5s are the same or different from each other, and a plurality of R _6s are the same or different from each other.

R ₃ to R ₆ 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 (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C ₆₀ arylboron group, C ₆ to C 60 arylphosphine group, C ₆ to C ₆₀ arylphosphine oxide group and C ₆ to C ₆₀ arylamine group, or is selected from the group consisting of an adjacent group (e.g., R ₃ -R ₃ , R _{4 -R 4 ,} R ₅ -R ₅ , R ₆ -R ₆ , R ₃ -R ₄ , R ₄ -L ₁ , R ₄ -R ₅ , R ₅ -L ₁ , R ₅ -R ₆ , R ₆ -R ₃ ) to form a condensed ring. Specifically, R ₃ to R ₆ are the same or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium (D), a C ₁ to C ₂₀ alkyl group, a C ₆ to C ₃₀ aryl group, a C ₂ to C ₃₀ heteroaryl group, a C ₆ to C ₃₀ arylphosphine oxide group, and a C ₆ to C ₃₀ arylamine group, or may be condensed with adjacent groups (e.g., R ₃ -R ₃ , R ₄ -R ₄ , R ₅ -R ₅ , R ₆ -R ₆ , R ₃ -R ₄ , R ₄ -L ₁ , R ₄ -R ₅ , R ₅ -L ₁ , R ₅ -R ₆ , R ₆ -R ₃ ) to form a condensed ring, and more specifically, each independently selected from hydrogen, deuterium (D), a cyano group (-CN), A group selected from the group consisting of 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 phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a triphenylenyl group, a phenanthryl group, a fluorenyl group, an anthracenyl group, an anthryl group, a pyrenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a phenoxathienyl group, an indolizinyl group, an indolyl group, a purinyl group, a quinolyl group, a benzothiazole group, a dibenzofuran group, a dibenzothiophene group, a phenanthrolinyl group, and a carbazolyl group, or an adjacent group (e.g., R ₃ -R ₃ , R ₄ -R ₄ , R ₅ -R ₅ , R ₆ -R ₆ , R ₃ -R ₄ , R ₄ -L ₁ , R ₄ -R ₅ , R ₅ -L ₁ , R ₅ -R ₆ , R ₆ -R ₃ ) can be condensed to form a condensed ring. Here, the condensed ring may be at least one selected from the group consisting of a C ₃ to C ₆₀ condensed aliphatic ring (specifically, a C ₃ to C ₃₀ condensed aliphatic ring), a C ₆ to C ₆₀ condensed aromatic ring (specifically, a C ₆ to C ₃₀ condensed aromatic ring), a 5- to 60-membered condensed heteroaromatic ring containing a heteroatom such as N, O or S (specifically, a 5- to 30-membered condensed heteroaromatic ring), a C ₃ to C ₆₀ spiro ring, and combinations thereof.

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 R 3 to R 6 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, and 3 to 40 nuclear atoms. A heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylborone group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group, which is unsubstituted or substituted with one or more substituents selected from the group consisting of a deuterium (D), a halogen (e.g., -F, -Cl, -Br, -I, etc.), a cyano group (-CN), a nitro group (-NO ₂ ), It may be substituted or _{unsubstituted with one or more substituents selected from the group consisting of an amino group (-NH 2 ), a hydroxy group (-OH), a C 1 to C 12 alkyl} group, a C ₆ to C ₁₈ aryl group, a heteroaryl group having 5 to 18 nuclear atoms, and a C 6 to C 18 arylamine group, or the substituents may be condensed with each other to form a condensed ring. If there are multiple substituents, they may be the same or different.

The organic compound represented by the above chemical formula 1 may be a compound represented by any one of the following chemical formulas 11 to 82, but is not limited thereto.

In the above chemical formulas 11 to 82,

X ₁ to X ₃ , Ar ₁ , L ₁ , L ₂ , n, m, c, d, e, f and R ₁ to R ₆ are each as defined in the above chemical formula 1,

Plural n's are the same or different from each other,

Plural m are the same or different,

n1 is an integer from 1 to 4,

m1 is an integer from 1 to 5,

q1 to q4 are integers from 0 to 5, respectively,

q5 is an integer from 0 to 7,

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

R is hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C It is selected from the group consisting of an alkylboron group of ₄₀ , an arylborone group of C ₆ to C ₆₀ , an arylphosphine group of C _{6 to} C ₆₀ , an arylphosphine oxide group of C ₆ to C ₆₀ , and an arylamine group of C 6 to C ₆₀ , and specifically, it can be selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I _, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), an alkyl group of C ₁ to C ₂₀ , an aryl group of C 6 to C ₃₀ , a heteroaryl group having 5 to 30 nuclear atoms, an arylphosphine oxide group of C ₆ to C ₃₀ , and an arylamine group of C ₆ to C ₃₀ ,

W is selected from the group consisting of O, S, C(Ar ₁₃ )(Ar ₁₄ ), Si(Ar ₁₅ )(Ar ₁₆ ) and N(Ar ₁₇ ),

Ar ₁₃ to Ar ₁₇ 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 (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ ~C ₆₀ arylsilyl group, C ₁ ~C ₄₀ alkylboron group, C ₆ ~C ₆₀ arylboron group, C ₆ ~C ₆₀ arylphosphine group, C ₆ ~C ₆₀ arylphosphine oxide group and C ₆ ~C ₆₀ arylamine group, or condensed with adjacent groups (e.g., Ar ₁₃ -Ar ₁₄ , Ar ₁₅ -Ar ₁₆ , Ar _{13 -R, Ar 15} -R, Ar _{17 -R} ) to form a condensed ring, and specifically, each independently hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO ₂ ), amino group (-NH ₂ ), hydroxy group (-OH), C ₁ ~C ₂₀ alkyl group, C ₆ ~C It is selected from the group consisting of an aryl group of ₃₀ , a heteroaryl group of C ₂ to C ₃₀ , an arylphosphine oxide group of C ₆ to C ₃₀ , and an arylamine group of C ₆ to C ₃₀ , or can form a condensed ring by condensation with an adjacent group (e.g., Ar ₁₃ -Ar ₁₄ , Ar ₁₅ -Ar ₁₆ , Ar ₁₃ -R, Ar ₁₅ -R, Ar ₁₇ -R). Here, the condensed ring may be at least one selected from the group consisting of a C ₃ to C ₆₀ condensed aliphatic ring (specifically, a C ₃ to C ₃₀ condensed aliphatic ring), a C ₆ to C ₆₀ condensed aromatic ring (specifically, a C ₆ to C ₃₀ condensed aromatic ring), a 5- to 60-membered condensed heteroaromatic ring containing a heteroatom such as N, O or S (specifically, a 5- to 30-membered condensed heteroaromatic ring), a C ₃ to C ₆₀ spiro ring, and combinations thereof.

The compound represented by the above-mentioned chemical formula 1 can be further specified as compounds 1 to 227 below, but is not limited thereto.

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.

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.

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.

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.

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

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

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.

In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon atom in the ring, preferably 1 to 3 carbon atom, is substituted with a heteroatom such as N, O, S, or Se. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may be included, and a form condensed with an aryl group may also be included. Examples of such heteroaryls include, but are not limited to, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, 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. Here, the number of nuclear atoms means the number of atoms forming the ring, i.e., the number of atoms in the ring.

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.

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.

In the present invention, “alkylsilyl” means silyl substituted with alkyl having 1 to 40 carbon atoms, and includes not only mono- but also di- and tri-alkylsilyl.

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

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.

In the present invention, “alkylphosphinyl group” means a phosphine group substituted with an alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-alkylphosphinyl groups.

In addition, 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.

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

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.

In the present invention, "fused ring" means a fused aliphatic ring having 3 to 40 carbon atoms, a fused aromatic ring having 6 to 60 carbon atoms, a fused heteroaliphatic ring having 3 to 60 nuclear atoms, a fused heteroaromatic ring having 5 to 60 nuclear atoms, a C ₃ to C ₆₀ spiro ring, or a combination thereof. Here, the number of nuclear atoms means the number of atoms forming the ring, i.e., the number of ring atoms.

Organic electroluminescent devices

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

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 an organic 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.

The organic layer (300) of one or more layers may include at least one 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 an organic compound represented by the chemical formula 1. Specifically, the organic layer including the compound of 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), and specifically, may be at least one of the electron transport layer (340) and the electron transport auxiliary layer (360).

According to an example, the organic 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 an organic compound represented by the above chemical formula 1. In this case, the organic 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 of the above chemical formula 1, and can also move quickly 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 of the above chemical formula 1 has excellent thermal stability and electrochemical stability, and can improve the performance of the organic electroluminescent device.

The compound of chemical formula 1 may be used alone or in combination with an electron transport layer material known in the art.

In the present invention, the electron transport layer material that can be mixed with the compound of the above chemical formula 1 includes an electron transport material commonly known in the art. Non-limiting examples of electron transport materials that can be used include oxazole compounds, isoxazole compounds, triazole compounds, isothiazole compounds, oxadiazole compounds, thiadiazole compounds, perylene compounds, aluminum complexes (e.g., Alq _3, tris(8-quinolinolato)-aluminium), gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. These may be used alone or in combination of two or more.

In the present invention, when the compound of 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 controlled within a range known in the art.

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 an organic 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 of the chemical formula 1 has a high triplet energy. Therefore, when the compound of 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 of 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.

The compound of chemical formula 1 may be used alone or in combination with an electron transport layer auxiliary layer material known in the art.

In the present invention, the electron transport auxiliary layer material that can be mixed with the compound of 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.

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.

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).

The organic electroluminescent device of the present invention can be manufactured by forming the organic layer and 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 an organic compound represented by the chemical formula 1.

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.

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.

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 SnO ₂ :Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black.

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 LiO ₂ /Al.

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.

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.

[Preparation Example 1] Synthesis of 2-chloro-4-phenyl-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine

100 g (442.35 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine and 67.40 g (177.21 mmol) of (3-(triphenylsilyl)phenyl)boronic acid were added to 1000 ml of 1,4-dioxane and 300 ml of H ₂ O, along with 6.14 g (5.32 mmol) of Pd(pph ₃ ) ₄ and 48.99 g (354.43 mmol) of K ₂ CO ₃ , and the mixture was heated and stirred under reflux for 4 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, dried over MgSO ₄ , and filtered. After filtering, the organic layer solvent was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain SA-1 (51 g, yield: 54.70%).

1H-NMR: δ 8.38(d, 1H), 8.36(d, 2H), 7.88(s, 1H), 7.64(t, 1H), 7.56(d, 1H), 7.50(t, 3H), 7.46(d, 6H), 7.38(t, 9H)

Mass: [(M+H) ⁺ ]: 526

[Preparation Example 2] Synthesis of 2-chloro-4-phenyl-6-(3-(triphenylsilyl)phenyl)pyrimidine

100 g (442.01 mmol) of 2,4-dichloro-6-phenylpyrimidine and 67.07 g (178.00 mmol) of (3-(triphenylsilyl)phenyl)boronic acid were added to 1000 ml of 1,4-dioxane and 300 ml of H ₂ O, together with 10.28 g (8.90 mmol) of Pd(pph ₃ ) ₄ and 49.20 g (356.0.1 mmol) of K ₂ CO ₃ , and the mixture was heated and refluxed for 4 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, dried with MgSO ₄ , and filtered. After filtering, the organic layer solvent was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. After filtering the solid, it was washed with methanol and dried in an oven to obtain SA-2 (52 g, yield: 55.63%).

1H-NMR: δ 8.33(s, 1H), 7.94(d, 3H), 7.88(s, 1H), 7.64(t, 1H), 7.56(d, 1H), 7.55(t, 2H), 7.49(t, 1H), 7.46(d, 6H), 7.38(t, 9H)

Mass: [(M+H) ⁺ ]: 393

[Preparation Example 3] Synthesis of 4-(3-([1,1'-biphenyl]-3-yldiphenylsilyl)phenyl)-2-chloro-6-phenylpyrimidine

100 g (444.77 mmol) of 2,4-dichloro-6-phenylpyrimidine and 81.20 g (177.91 mmol) of (3-([1,1'-biphenyl]-3-yldiphenylsilyl)phenyl)boronic acid were added to 1000 ml of 1,4-dioxane and 300 ml of H ₂ O, along with 10.28 g (8.90 mmol) of Pd(pph ₃ ) ₄ and 49.18 g (355.81 mmol) of K ₂ CO ₃ , and the mixture was heated and stirred under reflux for 4 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, dried with MgSO ₄ , and filtered. After filtering, the organic layer solvent was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. After filtering the solid, it was washed with methanol and dried in an oven to obtain SA-3 (58 g, yield: 54.22%).

1H-NMR: δ 8.33(s, 1H), 7.94(d, 3H), 7.88(s, 2H), 7.75(d, 2H), 7.64(t, 2H), 7.61(d, 1H), 7.56(d, 2H), 7.55(t, 2H), 7.49(t, 3H), 7.46(d, 4H), 7.38(t, 6H), 7.41(t, 1H)

Mass: [(M+H) ⁺ ]: 601

[Preparation Example 4] Synthesis of 2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine

100 g (207.02 mmol) of 2,4-dichloro-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine and 22.07 g (82.81 mmol) of [1,1':3',1''-terphenyl]-5'-ylboronic acid were added to 1000 ml of 1,4-dioxane and 300 ml of H ₂ O, along with 2.87 g (2.48 mmol) of Pd(pph ₃ ) ₄ and 22.89 g (165.61 mmol) of K ₂ CO ₃ , and the mixture was heated and stirred under reflux for 4 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added to remove moisture, and then filtered. After filtration, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain SA-4 (33 g, yield: 58.75%).

1H-NMR: δ 8.38(d, 1H), 8.04(s, 3H), 7.88(s, 1H), 7.75(d, 4H), 7.64(t, 1H), 7.56(d, 1H), 7.49(t, 4H), 7.46(d, 6H), 7.41(t, 2H), 7.38(t, 9H)

Mass: [(M+H) ⁺ ]: 678

[Preparation Example 5] 2-chloro-4-phenyl-6-(4-(triphenylsilyl)phenyl)-1,3,5-triazine

100 g (442.38 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine and 67.30 g (176.95 mmol) of (4-(triphenylsilyl)phenyl)boronic acid were added to 1000 ml of 1,4-dioxane and 300 ml of H ₂ O, together with 10.22 g (8.85 mmol) of Pd(pph ₃ ) ₄ and 48.91 g (353.90 mmol) of K ₂ CO ₃ , and the mixture was heated and stirred under reflux for 4 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, dried over MgSO ₄ , and then filtered. After filtering, the organic layer solvent was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain SA-5 (52 g, yield: 55.86%).

1H-NMR: δ 8.36(d, 2H), 7.88(d, 2H), 7.65(d, 2H), 7.50(t, 3H), 7.46(d, 6H), 7.38(t, 9H)

Mass: [(M+H) ⁺ ]: 526

[Synthesis Example 1] Synthesis of Compound 15

In Preparation Example 1, 8 g (15.21 mmol) of SA-1 synthesized and 5.86 g (16.73 mmol) of [1,1':2',1'':2'',1'''-quaterphenyl]-2-ylboronic acid were added together with 0.88 g (0.76 mmol) of Pd(pph ₃ ) ₄ and 4.20 g (30.41 mmol) of K ₂ CO ₃ in 160 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O, and heated and stirred under reflux for 5 hours. After completion of the reaction, the mixture was extracted with dichloromethane, dried over MgSO ₄ , and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. After filtering the solid, it was washed with methanol and dried in an oven to obtain compound 15 (8.4 g, yield: 69.39%).

Mass: [(M+H) ⁺ ]: 796

[Synthesis Example 2] Synthesis of Compound 17

In Preparation Example 1, 6.0 g (11.40 mmol) of SA-1 synthesized and 4.39 g (12.54 mmol) of [1,1':2',1'':3'',1'''-quaterphenyl]-2-ylboronic acid were added together with 0.66 g (0.57 mmol) of Pd(pph ₃ ) ₄ and 3.15 g (22.81 mmol) of K ₂ CO ₃ to 120 ml of toluene, 30 ml of EtOH, and 30 ml of H ₂ O, and the mixture was heated and stirred under reflux for 4 hours. After completion of the reaction, the mixture was extracted with dichloromethane, dried with MgSO ₄ , and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. After filtering the solid, it was washed with methanol and dried in an oven to obtain compound 17 (7.1 g, yield: 78.20%).

Mass: [(M+H) ⁺ ]: 796

[Synthesis Example 3] Synthesis of Compound 24

In Preparation Example 1, 6.0 g (11.40 mmol) of SA-1 synthesized and 4.39 g (12.54 mmol) of [1,1':2',1'':4'',1'''-quaterphenyl]-2'''-ylboronic acid were added together with 0.66 g (0.57 mmol) of Pd(pph ₃ ) ₄ and 3.15 g (22.81 mmol) of K ₂ CO ₃ to 120 ml of toluene, 30 ml of EtOH, and 30 ml of H ₂ O, and the mixture was heated and stirred under reflux for 4 hours. After completion of the reaction, the mixture was extracted with dichloromethane, dried with MgSO ₄ , and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. After filtering the solid, it was washed with methanol and dried in an oven to obtain compound 24 (6.4 g, yield: 70.50%).

Mass: [(M+H) ⁺ ]: 796

[Synthesis Example 4] Synthesis of Compound 27

In Preparation Example 1, 8.0 g (15.21 mmol) of SA-1 synthesized and 5.86 g (16.73 mmol) of [1,1':2',1'':2'',1'''-quaterphenyl]-3-ylboronic acid were added together with 0.88 g (0.76 mmol) of Pd(pph ₃ ) ₄ and 4.20 g (30.41 mmol) of K ₂ CO ₃ to 160 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O, and the mixture was heated and stirred under reflux for 4 hours. After completion of the reaction, the mixture was extracted with dichloromethane, dried with MgSO ₄ , and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. After filtering the solid, it was washed with methanol and dried in an oven to obtain compound 27 (9.1 g, yield: 75.18%).

Mass: [(M+H) ⁺ ]: 796

[Synthesis Example 5] Synthesis of Compound 34

In Preparation Example 2, 8.0 g (15.23 mmol) of SA-2 synthesized and 5.86 g (16.76 mmol) of [1,1':2',1'':2'',1'''-quaterphenyl]-4-ylboronic acid were added together with 0.88 g (0.76 mmol) of Pd(pph ₃ ) ₄ and 4.21 g (30.47 mmol) of K ₂ CO ₃ to 160 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O, and the mixture was heated and stirred under reflux for 4 hours. After completion of the reaction, the mixture was extracted with dichloromethane, dried with MgSO ₄ , and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. After filtering the solid, it was washed with methanol and dried in an oven to obtain compound 34 (8.7 g, yield: 71.83%).

Mass: [(M+H) ⁺ ]: 795

[Synthesis Example 6] Synthesis of Compound 37

In Preparation Example 1, 8.0 g (15.21 mmol) of SA-1 synthesized and 5.86 g (16.73 mmol) of (6'-phenyl-[1,1':2',1''-terphenyl]-4'-yl)boronic acid were added together with 0.88 g (0.76 mmol) of Pd(pph ₃ ) ₄ and 4.20 g (30.41 mmol) of K ₂ CO ₃ to 160 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was extracted with dichloromethane, dried with MgSO ₄ , and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. After filtering the solid, it was washed with methanol and dried in an oven to obtain compound 37 (8.8 g, yield: 72.69%).

Mass: [(M+H) ⁺ ]: 796

[Synthesis Example 7] Synthesis of Compound 42

In Preparation Example 1, 8.0 g (15.21 mmol) of SA-1 synthesized and 6.09 g (16.73 mmol) of (5-(dibenzo[b,d]furan-2-yl)-[1,1'-biphenyl]-2-yl)boronic acid were added together with 0.88 g (0.76 mmol) of Pd(pph ₃ ) ₄ and 4.20 g (30.41 mmol) of K ₂ CO ₃ in 160 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O, and heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was extracted with dichloromethane, dried over MgSO ₄ , and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. After filtering the solid, it was washed with methanol and dried in an oven to obtain compound 42 (10.2 g, yield: 82.81%).

Mass: [(M+H) ⁺ ]: 810

[Synthesis Example 8] Synthesis of Compound 44

In Preparation Example 1, 8.0 g (15.21 mmol) of SA-1 synthesized and 5.42 g (16.73 mmol) of (5-(naphthalen-1-yl)-[1,1'-biphenyl]-3-yl)boronic acid were added together with 0.88 g (0.76 mmol) of Pd(pph ₃ ) ₄ and 4.20 g (30.41 mmol) of K ₂ CO ₃ in 160 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O, and the mixture was heated and stirred under reflux for 4 hours. After completion of the reaction, the mixture was extracted with dichloromethane, dried over MgSO ₄ , and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. After filtering the solid, it was washed with methanol and dried in an oven to obtain compound 44 (10.4 g, yield: 88.82%).

Mass: [(M+H) ⁺ ]: 770

[Synthesis Example 9] Synthesis of Compound 50

In Preparation Example 1, 8.0 g (15.21 mmol) of SA-1 synthesized and 7.13 g (16.73 mmol) of (2',3'-diphenyl-[1,1':4',1''-terphenyl]-4-yl)boronic acid were added together with 0.88 g (0.76 mmol) of Pd(pph ₃ ) ₄ and 4.20 g (30.41 mmol) of K ₂ CO ₃ in 160 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O, and the mixture was heated and stirred under reflux for 5 hours. After completion of the reaction, the mixture was extracted with dichloromethane, dried over MgSO ₄ , and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. After filtering the solid, it was washed with methanol and dried in an oven to obtain compound 50 (8.4 g, yield: 63.34%).

Mass: [(M+H) ⁺ ]: 872

[Synthesis Example 10] Synthesis of Compound 61

In Preparation Example 1, 8.0 g (15.21 mmol) of SA-1 synthesized and 7.13 g (16.73 mmol) of [1,1':2',1'':2'',1''':2''',1''''-quinquephenyl]-3-ylboronic acid were added together with 0.88 g (0.76 mmol) of Pd(pph ₃ ) ₄ and 4.20 g (30.41 mmol) of K ₂ CO ₃ in 160 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O, and heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was extracted with dichloromethane, dried over MgSO ₄ , and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. After filtering the solid, it was washed with methanol and dried in an oven to obtain compound 61 (10.1 g, yield: 76.15%).

Mass: [(M+H) ⁺ ]: 872

[Synthesis Example 11] Synthesis of Compound 62

In Preparation Example 5, 8.0 g (15.21 mmol) of SA-5 synthesized and 7.13 g (16.73 mmol) of (2',6'-diphenyl-[1,1':4',1''-terphenyl]-4-yl)boronic acid were added together with 0.88 g (0.76 mmol) of Pd(pph ₃ ) ₄ and 4.20 g (30.41 mmol) of K ₂ CO ₃ in 160 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O, and the mixture was heated and stirred under reflux for 5 hours. After completion of the reaction, the mixture was extracted with dichloromethane, dried over MgSO ₄ , and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. After filtering the solid, it was washed with methanol and dried in an oven to obtain compound 62 (9.7 g, yield: 73.14%).

Mass: [(M+H) ⁺ ]: 872

[Synthesis Example 12] Synthesis of Compound 69

In Preparation Example 1, 8.0 g (15.21 mmol) of SA-1 synthesized and 7.13 g (16.73 mmol) of (5''-phenyl-[1,1':3',1'':3'',1'''-quaterphenyl]-3-yl)boronic acid were added together with 0.88 g (0.76 mmol) of Pd(pph ₃ ) ₄ and 4.20 g (30.41 mmol) of K ₂ CO ₃ in 160 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O, and the mixture was heated and stirred under reflux for 4 hours. After completion of the reaction, the mixture was extracted with dichloromethane, dried over MgSO ₄ , and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. After filtering the solid, it was washed with methanol and dried in an oven to obtain compound 69 (8.5 g, yield: 64.10%).

Mass: [(M+H) ⁺ ]: 872

[Synthesis Example 13] Synthesis of Compound 77

In Preparation Example 1, 8.0 g (15.21 mmol) of SA-1 synthesized and 7.13 g (16.73 mmol) of (3',5'-diphenyl-[1,1':2',1''-terphenyl]-3-yl)boronic acid were added together with 0.88 g (0.76 mmol) of Pd(pph ₃ ) ₄ and 4.20 g (30.41 mmol) of K ₂ CO ₃ in 160 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O, and the mixture was heated and stirred under reflux for 6 hours. After completion of the reaction, the mixture was extracted with dichloromethane, dried over MgSO ₄ , and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. After filtering the solid, it was washed with methanol and dried in an oven to obtain compound 77 (8.3 g, yield: 62.58%).

Mass: [(M+H) ⁺ ]: 872

[Synthesis Example 14] Synthesis of Compound 134

In Preparation Example 3, 8.0 g (13.31 mmol) of SA-3 synthesized and 5.13 g (14.64 mmol) of [1,1':2',1'':2'',1'''-quaterphenyl]-3-ylboronic acid were added together with 0.77 g (0.67 mmol) of Pd(pph ₃ ) ₄ and 3.68 g (26.61 mmol) of K ₂ CO ₃ in 160 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O, and the mixture was heated and stirred under reflux for 5 hours. After completion of the reaction, the mixture was extracted with dichloromethane, dried over MgSO ₄ , and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. After filtering the solid, it was washed with methanol and dried in an oven to obtain compound 134 (9.4 g, yield: 81.09%).

Mass: [(M+H) ⁺ ]: 871

[Synthesis Example 15] Synthesis of Compound 161

In Preparation Example 4, 8.0 g (11.79 mmol) of SA-4 synthesized and 2.75 g (12.97 mmol) of ([1,1':3',1''-terphenyl]-5'-ylboronic acid) were added together with 0.68 g (0.59 mmol) of Pd(pph ₃ ) ₄ and 3.26 g (23.59 mmol) of K ₂ CO ₃ in 160 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O, and heated and stirred under reflux for 4 hours. After completion of the reaction, the mixture was extracted with dichloromethane, and MgSO ₄ was added to remove moisture, followed by filtering. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. After filtering the solid, it was washed with methanol, and dried in an oven to obtain compound 161. (7.7 g, yield: 80.59%) was obtained.

Mass: [(M+H) ⁺ ]: 810

[Synthesis Example 16] Synthesis of Compound 197

In Preparation Example 4, 8.0 g (11.79 mmol) of SA-4 synthesized and 3.73 g (12.97 mmol) of (9-phenyl-9H-carbazol-4-yl)boronic acid were added together with 0.68 g (0.59 mmol) of Pd(pph ₃ ) ₄ and 3.26 g (23.59 mmol) of K ₂ CO ₃ in 160 ml of toluene, 40 ml of EtOH, and 40 ml of H ₂ O, and the mixture was heated and stirred under reflux for 5 hours. After completion of the reaction, the mixture was extracted with dichloromethane, dried over MgSO ₄ , and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. After filtering the solid, it was washed with methanol and dried in an oven to obtain compound 197 (7.4 g, yield: 70.88%).

Mass: [(M+H) ⁺ ]: 885

[Example 1] Fabrication of a blue organic electroluminescent device

Compound 15 synthesized in the above 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.

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.

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 15 + 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 are as follows, respectively.

[Examples 2 to 16] Preparation of blue organic electroluminescent devices

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that each compound described in Table 1 was used instead of compound 15 used as an electron transport layer material in Example 1.

[Comparative Examples 1 to 9] Manufacturing of blue organic electroluminescent devices

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq ₃ , BT-1, BT-2, BT-3, BT-4, BT-5, BT-6, BT-7, and BT-8 were used instead of compound 15 used as an electron transport layer material in Example 1. At this time, the structures of Alq ₃ , BT-1, BT-2, BT-3, BT-4, BT-5, BT-6, BT-7, and BT-8 used are as follows, respectively.

[Evaluation Example 1]

For the organic electroluminescent devices manufactured in Examples 1 to 16 and Comparative Examples 1 to 9, 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.

sample electron transport layer material Driving voltage (V) Luminescence peak (nm) Current efficiency (cd/A) Example 1 Compound 15 3.4 454 8.0 Example 2 Compound 17 3.5 455 7.6 Example 3 Compound 24 3.4 455 7.9 Example 4 Compound 27 3.3 454 8.1 Example 5 Compound 34 3.3 455 8.0 Example 6 Compound 37 3.5 455 7.7 Example 7 Compound 42 3.4 454 7.8 Example 8 Compound 44 3.5 455 7.8 Example 9 Compound 50 3.4 455 7.9 Example 10 Compound 61 3.2 454 8.1 Example 11 Compound 62 3.5 455 7.7 Example 12 Compound 69 3.4 454 7.9 Example 13 Compound 77 3.2 456 8.2 Example 14 Compound 134 3.4 455 7.9 Example 15 Compound 161 3.3 455 8.2 Example 16 Compound 197 3.3 455 8.1 Comparative Example 1 Alq ₃ 4.6 457 5.6 Comparative Example 2 BT-1 4.3 457 6.6 Comparative Example 3 BT-2 4.2 457 6.8 Comparative Example 4 BT-3 4.2 456 6.9 Comparative Example 5 BT-4 4.1 455 7.2 Comparative Example 6 BT-5 4.4 456 6.6 Comparative Example 7 BT-6 4.2 457 6.8 Comparative Example 8 BT-7 4.4 456 6.7 Comparative Example 9 BT-8 4.2 455 7.2

From the above Table 1, it was confirmed that the organic light-emitting devices manufactured in Examples 1 to 16 had superior driving voltage, emission peak, and current efficiency compared to the organic light-emitting devices manufactured in Comparative Examples 1 to 9.

[Example 17] Fabrication of a blue organic electroluminescent device

Compound 15 synthesized in the above 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.

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.

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 15 (5 nm)/ET + Liq (1:1 weight ratio) (30 nm)/LiF (1 nm)/Al (100 nm) in that order. The structures of HI, HAT-CN6, EB, BH, BD, and Liq used here are the same as those described in Example 1 and are therefore omitted, and the structure of ET is as follows.

[Examples 18 to 32] Preparation of blue organic electroluminescent devices

A blue organic electroluminescent device was manufactured in the same manner as in Example 17, except that the compounds described in Table 2 below were used instead of Compound 15, which was used as an electron transport auxiliary layer material in Example 17.

[Comparative Example 10]

A blue organic electroluminescent device was manufactured in the same manner as in Example 17, except that the electron transport auxiliary layer was not formed with compound 1.

[Comparative Examples 11 to 18] Manufacturing of blue organic electroluminescent devices

A blue organic electroluminescent device was manufactured in the same manner as in Example 17, except that BT-1, BT-2, BT-3, BT-4, BT-5, BT-6, BT-7, and BT-8 were used instead of Compound 15, which was used as an electron transport auxiliary layer material in Example 17. The structures of BT-1, BT-2, BT-3, BT-4, BT-5, BT-6, BT-7, and BT-8 used here are the same as those described in Comparative Examples 2 to 9, and therefore are omitted.

[Evaluation Example 2]

For the organic electroluminescent devices manufactured in Examples 17 to 32 and Comparative Examples 10 to 18, 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 2 below.

sample Electron transport auxiliary layer material Driving voltage (V) Luminescence peak (nm) Current efficiency (cd/A) Example 17 Compound 15 3.3 454 8.0 Example 18 Compound 17 3.4 455 8.0 Example 19 Compound 24 3.2 454 8.2 Example 20 Compound 27 3.5 454 7.8 Example 21 Compound 34 3.3 455 8.0 Example 22 Compound 37 3.2 455 8.0 Example 23 Compound 42 3.3 455 8.1 Example 24 Compound 44 3.4 455 7.9 Example 25 Compound 50 3.2 454 8.2 Example 26 Compound 61 3.1 454 8.3 Example 27 Compound 62 3.2 454 8.2 Example 28 Compound 69 3.3 455 7.9 Example 29 Compound 77 3.1 454 8.4 Example 30 Compound 134 3.2 454 8.1 Example 31 Compound 161 3.2 456 8.2 Example 32 Compound 197 3.1 455 8.2 Comparative Example 10 - 4.6 456 6.3 Comparative Example 11 BT-1 4.2 456 6.7 Comparative Example 12 BT-2 4.0 455 6.9 Comparative Example 13 BT-3 3.8 455 7.0 Comparative Example 14 BT-4 3.9 455 7.1 Comparative Example 15 BT-5 4.2 455 6.7 Comparative Example 16 BT-6 4.0 456 6.8 Comparative Example 17 BT-7 3.9 456 7.0 Comparative Example 18 BT-8 4.1 455 6.9

From Table 2 above, it was confirmed that the organic light-emitting devices manufactured in Examples 17 to 32 had superior driving voltage, luminescence peak, and current efficiency compared to the organic light-emitting devices manufactured in Comparative Examples 10 to 18.

100: positive, 200: negative,
300: Organic layer, 310: Hole injection layer,
320: hole transport layer, 330: light emitting layer,
340: electron transport layer, 350: electron injection layer,
360: Electron transport auxiliary layer

Claims (13)

An organic compound represented by the following chemical formula 1:
[Chemical Formula 1]

(In the above chemical formula 1,
X ₁ to X ₃ are the same or different from each other, and are each independently N or C(Ar ₂ ), provided that at least one of X ₁ to X ₃ is N;
Ar ₁ and Ar ₂ are the same or different from each other, and each independently represent hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C Selected from the group consisting of an arylborone group of ₆₀ , an arylphosphine group of C ₆ to C ₆₀ , an arylphosphine oxide group of C ₆ to C ₆₀ , and an arylamine group of C ₆ to C ₆₀ ;
L ₁ and L ₂ are the same or different from each other, and each independently represents a single bond or is selected from the group consisting of an arylene group having C ₆ to C ₂₄ and a heteroarylene group having 5 to 24 nuclear atoms;
Ring Cy1 is present or absent, and when ring Cy1 is present, ring Cy1 is a six-membered fused aromatic ring;
a and b are integers from 0 to 2, respectively,
n and m are integers from 0 to 5, respectively.
However, if a+b≥1, and in this case a+b=1, then n+m≥1, and if a+b≥2, then n+m≥0;
Multiple R ₁ 's are the same or different from each other,
Multiple R ₂ are the same or different,
R ₁ and R ₂ are the same or different from each other, and are each independently selected from the group consisting of an aryl group having C ₆ to C ₆₀ and a heteroaryl group having 5 to 60 nuclear atoms, or are condensed with an adjacent group to form a condensed ring;
c, e and f are integers from 0 to 5, respectively.
d is an integer from 0 to 4,
Multiple R ₃ 's are the same or different from each other,
Multiple R ₄ 's are the same or different,
Multiple R ₅ 's are the same or different from each other,
Multiple R ₆ are the same or different,
R ₃ to R ₆ are the same or different from each other, and each independently represent hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C Selected from the group consisting of an arylboron group of ₆₀ , an arylphosphine group of C ₆ to C ₆₀ , an arylphosphine oxide group of C ₆ to C ₆₀ , and an arylamine group of C ₆ to C ₆₀ , or condensed with an adjacent group to form a condensed ring;
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 Ar 1 and Ar 2, the arylene group and heteroarylene group of the above L ₁ and L ₂ , the aryl group, heteroaryl group and condensed ring of the above R _{1 and} R _{2 ,} 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, The arylphosphine oxide group, the arylamine group and the condensed ring are each independently selected from the group _consisting of deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C ₁ ~C ₄₀ alkyl group, C ₂ ~C ₄₀ alkenyl group, C ₂ ~C ₄₀ alkynyl group, C ₃ ~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~C ₄₀ alkyloxy group, C ₆ ~C ₆₀ aryloxy group, C ₁ ~C ₄₀ alkylsilyl group, C ₆ ~C ₆₀ arylsilyl group, C ₁ ~C ₄₀ alkylboron group, C ₆ ~C ₆₀ (Substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl boron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group, or the substituents are condensed with each other to form a condensed ring, and in this case, when there are multiple substituents, they are the same or different from each other.) In the first paragraph,
The organic compound represented by the above chemical formula 1 is an organic compound represented by any one of the following chemical formulas 2 to 4:
[Chemical Formula 2]

[Chemical Formula 3]

[Chemical Formula 4]

(In the above chemical formulas 2 to 4,
X ₁ to X ₃ , Ar ₁ , L ₁ , L ₂ , ring Cy1, a, b, n, m, c, d, e, f and R ₁ to R ₆ are each as defined in paragraph 1). In the first paragraph,
An organic compound wherein the above X ₁ , X ₂ and X ₃ -containing ring moieties are selected from the group consisting of the following ring moieties Az1-1 to Az1-7:

(In the above ring moieties Az1-1 to Az1-7,
Ar ₁ and Ar ₂ are each as defined in paragraph 1). In the first paragraph,
An organic compound wherein Ar ₁ and Ar ₂ are the same or different and are each independently hydrogen or selected from the group consisting of the following substituents S1-1 to S1-10:

(In the above substituents S1-1 to S1-10,
g, g1 and g2 are integers from 0 to 5, respectively,
h, h1, h2 are integers from 0 to 4, respectively.
i is an integer from 0 to 7,
j is an integer from 0 to 6,
k is an integer from 0 to 9,
l is an integer from 0 to 3,
Multiple R's are the same or different from each other,
R is deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ arylborone group, C ₆ ~ C ₆₀ Selected from the group consisting of an arylphosphine group, an arylphosphine oxide group of C ₆ ~C ₆₀ and an arylamine group of C ₆ ~C ₆₀ ,
Y ₁ is selected from the group consisting of O, S, C(Ar ₃ )(Ar ₄ ), Si(Ar ₅ )(Ar ₆ ) and N(Ar ₇ ),
Ar ₃ to Ar ₇ are the same or different from each other, and each independently represent hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C (Selected from the group consisting of an arylboron group of ₆₀ , an arylphosphine group of C ₆ ~C ₆₀ , an arylphosphine oxide group of C ₆ ~C ₆₀ , and an arylamine group of C ₆ ~C ₆₀ , or condensed with an adjacent group to form a condensed ring). In the first paragraph,
The organic compound represented by the above chemical formula 1 is an organic compound represented by any one of the following chemical formulas 5 to 10:
[Chemical Formula 5]

[Chemical Formula 6]

[Chemical Formula 7]

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical Formula 10]

(In the above chemical formulas 5 to 10,
X ₁ to X ₃ , Ar ₁ , L ₁ , L ₂ , a, b, n, m, R ₁ , R ₂ , c, d, e, f and R ₃ to R ₆ are each as defined in paragraph 1). In the first paragraph,
An organic compound wherein L ₁ and L ₂ are the same or different from each other, and each independently represents a single bond or is selected from the group consisting of the following linker groups L1-1 to L1-4:

(In the above linker groups L1-1 to L1-4,
o is an integer from 1 to 4,
p1 is an integer from 0 to 4,
p2 and p3 are integers from 0 to 6, respectively,
p4 is an integer from 0 to 7,
Multiple R's are the same or different from each other,
R is deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ arylborone group, C ₆ ~ C ₆₀ Selected from the group consisting of an arylphosphine group, an arylphosphine oxide group of C ₆ ~C ₆₀ and an arylamine group of C ₆ ~C ₆₀ ,
Z ₁ is selected from the group consisting of O, S, C(Ar ₈ )(Ar ₉ ), Si(Ar ₁₀ )(Ar ₁₁ ) and N(Ar ₁₂ ),
Ar ₈ to Ar ₁₂ are the same or different from each other, and each independently represent hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C (Selected from the group consisting of an arylboron group of ₆₀ , an arylphosphine group of C ₆ ~C ₆₀ , an arylphosphine oxide group of C ₆ ~C ₆₀ , and an arylamine group of C ₆ ~C ₆₀ , or condensed with an adjacent group to form a condensed ring). In paragraph 6,
L ₁ is a single bond,
L ₂ is a single bond or an organic compound selected from the group consisting of linker groups L1-1 to L1-4, In the first paragraph,
In the above chemical formula 1 An organic compound wherein the moiety is selected from the group consisting of the following moieties Mo1-1 to Mo1-24:






(In the above moieties Mo1-1 to Mo1-24,
n and m are as defined in Article 1, respectively,
Plural n's are the same or different from each other,
Plural m are the same or different,
n1 is an integer from 1 to 4,
m1 is an integer from 1 to 5,
q1 to q4 are integers from 0 to 5, respectively,
q5 is an integer from 0 to 7,
Multiple R's are the same or different from each other,
R is hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ arylborone group, C ₆ ~ C Selected from the group consisting of an arylphosphine group of ₆₀ , an arylphosphine oxide group of C ₆ ~C ₆₀ and an arylamine group of C ₆ ~C ₆₀ ,
W is selected from the group consisting of O, S, C(Ar ₁₃ )(Ar ₁₄ ), Si(Ar ₁₅ )(Ar ₁₆ ) and N(Ar ₁₇ ),
Ar ₁₃ to Ar ₁₇ are the same or different from each other, and each independently represent hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C (Selected from the group consisting of an arylboron group of ₆₀ , an arylphosphine group of C ₆ ~C ₆₀ , an arylphosphine oxide group of C ₆ ~C ₆₀ , and an arylamine group of C ₆ ~C ₆₀ , or condensed with an adjacent group to form a condensed ring). In the first paragraph,
In the above chemical formula 1 An organic compound wherein the moiety is selected from the group consisting of the following moieties Mo2-1 to Mo2-100:

















(In the above moieties Mo2-1 to Mo2-100,
* indicates a site that is combined with chemical formula 1,
W is selected from the group consisting of O, S, C(Ar ₁₃ )(Ar ₁₄ ), Si(Ar ₁₅ )(Ar ₁₆ ) and N(Ar ₁₇ ),
Ar ₁₃ to Ar ₁₇ are the same or different from each other, and each independently represent hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C (Selected from the group consisting of an arylboron group of ₆₀ , an arylphosphine group of C ₆ ~C ₆₀ , an arylphosphine oxide group of C ₆ ~C ₆₀ , and an arylamine group of C ₆ ~C ₆₀ , or condensed with an adjacent group to form a condensed ring). In the first paragraph,
The organic compound represented by the above chemical formula 1 is an organic compound represented by any one of the following chemical formulas 11 to 82:
[Chemical Formula 11]

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

[Chemical Formula 19]

[Chemical Formula 20]

[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]

[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]

[Chemical Formula 60]

[Chemical Formula 61]

[Chemical Formula 62]

[Chemical Formula 63]

[Chemical Formula 64]

[Chemical Formula 65]

[Chemical Formula 66]

[Chemical Formula 67]

[Chemical Formula 68]

[Chemical Formula 69]

[Chemical Formula 70]

[Chemical Formula 71]

[Chemical Formula 72]

[Chemical Formula 73]

[Chemical Formula 74]

[Chemical Formula 75]

[Chemical Formula 76]

[Chemical Formula 77]

[Chemical Formula 78]

[Chemical Formula 79]

[Chemical Formula 80]

[Chemical Formula 81]

[Chemical Formula 82]

(In the above chemical formulas 11 to 82,
X ₁ to X ₃ , Ar ₁ , L ₁ , L ₂ , n, m, c, d, e, f and R ₁ to R ₆ are each as defined in paragraph 1,
Plural n's are the same or different from each other,
Plural m are the same or different,
n1 is an integer from 1 to 4,
m1 is an integer from 1 to 5,
q1 to q4 are integers from 0 to 5, respectively,
q5 is an integer from 0 to 7,
Multiple R's are the same or different from each other,
R is hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ ~ C ₆₀ arylborone group, C ₆ ~ C Selected from the group consisting of an arylphosphine group of ₆₀ , an arylphosphine oxide group of C ₆ ~C ₆₀ and an arylamine group of C ₆ ~C ₆₀ ,
W is selected from the group consisting of O, S, C(Ar ₁₃ )(Ar ₁₄ ), Si(Ar ₁₅ )(Ar ₁₆ ) and N(Ar ₁₇ ),
Ar ₁₃ to Ar ₁₇ are the same or different from each other, and each independently represent hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C (Selected from the group consisting of an arylboron group of ₆₀ , an arylphosphine group of C ₆ ~C ₆₀ , an arylphosphine oxide group of C ₆ ~C ₆₀ , and an arylamine group of C ₆ ~C ₆₀ , or condensed with an adjacent group to form a condensed ring). In the first paragraph,
The organic compound represented by the above chemical formula 1 is an organic compound selected from the group consisting of the following organic compounds:











. An anode; a cathode; and at least one organic layer interposed between the anode and the cathode,
An organic electroluminescent device, wherein at least one of the organic layers of the above one or more layers comprises an organic compound as described in any one of claims 1 to 11. In Article 12,
An organic electroluminescent device, wherein the organic layer containing the organic compound is an electron transport layer or an electron transport auxiliary layer.