KR102879390B1 - Organic compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more specifically, to an organic compound having excellent electron transport capability and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifespan by including the same in one or more organic layers.

Description

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

The present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more particularly, to an organic compound having excellent heat resistance, electron transport and injection ability, luminescence ability, electrochemical stability, etc., 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.

Up to now, 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 , which have great advantages in terms of efficiency improvement, are used as blue, green, and red dopant materials, and 4,4-dicarbazolybiphenyl (CBP) is used 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 purpose of the present invention is to provide a novel organic compound that is excellent in heat resistance, electron transport and injection ability, luminescence ability, electrochemical stability, etc., and can be applied to organic electroluminescent devices.

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

The present invention provides an organic compound represented by the following chemical formula 1:

(In the above chemical formula 1,

L is an arylene group having C ₆ to C ₃₀ substituted with one or more R ₁ ,

When R ₁ is plural, they are the same or different, and each independently represents an alkyl group of C ₁ to C ₂₀ ,

A1 is a substituent represented by any one of the following chemical formulas 2 to 6,

[Chemical Formula 2] [Chemical Formula 3]

[Chemical Formula 4] [Chemical Formula 5]

[Chemical Formula 6]

In the above chemical formulas 2 to 6,

X ₁ is selected from the group consisting of C(G ₁ )(G ₂ ), S and O,

X ₂ , X ₃ and X ₄ are S or O respectively,

a and f are integers from 0 to 7,

b, d, e and g are integers from 0 to 8, respectively.

c is an integer from 0 to 4,

R ₂ to R ₈ are the same or different from each other, and each independently represent hydrogen, deuterium, a halogen group, a hydroxy group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a C ₁ to C ₆₀ alkyl group, a C ₂ to C ₆₀ alkenyl group, a C ₂ to C ₆₀ alkynyl group, a C ₃ to C ₆₀ cycloalkyl group, a heterocycloalkyl group having 3 to 60 nuclear atoms, a C ₃ to C ₆₀ cycloalkenyl group, a heterocycloalkenyl group having 3 to 60 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₆₀ is selected from the group consisting of an alkyloxy group, an aryloxy group having C ₆ to C ₆₀ , an alkylsilyl group having C ₁ to C ₆₀ , an arylsilyl group having C ₆ to C ₆₀ , an alkylboron group having C ₁ to C ₄₀ , an arylboron group having C ₆ to C ₆₀ , an arylphosphine group having C ₆ to C ₆₀ , an arylphosphine oxide group having C ₆ to C ₆₀ , and an arylamine group having C ₆ to C ₆₀ , or may be combined with adjacent groups to form a condensed aromatic ring or a condensed heteroaromatic ring.

G ₁ and G ₂ are the same or different from each other, and each independently represent hydrogen, deuterium, a halogen group, a hydroxy group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a C ₁ to C ₆₀ alkyl group, a C ₂ to C ₆₀ alkenyl group, a C ₂ to C ₆₀ alkynyl group, a C ₃ to C ₆₀ cycloalkyl group, a heterocycloalkyl group having 3 to 60 nuclear atoms, a C ₃ to C ₆₀ cycloalkenyl group, a heterocycloalkenyl group having 3 to 60 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₆₀ is selected from the group consisting of an alkyloxy group, an aryloxy group having C ₆ to C ₆₀ , an alkylsilyl group having C ₁ to C ₆₀ , an arylsilyl group having C ₆ to C ₆₀ , an alkylboron group having C ₁ to C ₄₀ , an arylboron group having C ₆ to C ₆₀ , an arylphosphine group having C ₆ to C ₆₀ , an arylphosphine oxide group having C ₆ to C ₆₀ , and an arylamine group having C ₆ to C ₆₀ , or may be combined with adjacent groups to form a condensed alicyclic ring, a condensed aromatic ring, or a condensed heteroaromatic ring.

Ring R is a monocyclic aromatic ring of C ₆ to C ₁₂ or a polycyclic aromatic ring of C ₆ to C ₂₀ ,

A2 is a substituent represented by the following chemical formula 7 or 8,

[Chemical Formula 7] [Chemical Formula 8]

In the above chemical formulas 7 and 8,

Y ₁ to Y ₃ are each independently C(G ₃ ) or N, provided that at least one of Y ₁ to Y ₃ is N,

One of Y ₄ to Y ₇ is C and is connected to L, and the remaining Y ₄ to Y ₇ and Y ₈ to Y ₁₁ are the same or different from each other and are each independently C(G ₄ ) or N, provided that at least one of Y ₄ to Y ₁₁ is N,

Z ₁ is S or O,

G ₃ and G ₄ are the same or different from each other, and each independently represent hydrogen, deuterium, a halogen group, a hydroxy group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a C ₁ to C ₆₀ alkyl group, a C ₂ to C ₆₀ alkenyl group, a C ₂ to C ₆₀ alkynyl group, a C ₃ to C ₆₀ cycloalkyl group, a heterocycloalkyl group having 3 to 60 nuclear atoms, a C ₃ to C ₆₀ cycloalkenyl group, a heterocycloalkenyl group having 3 to 60 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₆₀ Selected from the group consisting of an alkyloxy group, an aryloxy group having C ₆ to C ₆₀ , an alkylsilyl group having C ₁ to C ₆₀ , an arylsilyl group having C ₆ to C ₆₀ , an alkylboron group having C ₁ to C ₄₀ , an arylborone group having C ₆ to C ₆₀ , an arylphosphine group having C ₆ to C ₆₀ , an arylphosphine oxide group having C ₆ to C ₆₀ , and an arylamine group having C ₆ to C ₆₀ ,

The arylene group of the above L, the alkyl group of the above R ₁ , the hydrazino group of the above R ₂ to R ₈ , G ₁ to G _4, the hydrazono group, the alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, the heterocycloalkyl group, the cycloalkenyl group, the heterocycloalkenyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group and the arylamine group are each independently deuterium, a halogen group, a hydroxy group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a C ₁ to C ₆₀ alkyl group, a C ₂ to C ₆₀ Alkenyl group, C ₂ ~C ₆₀ alkynyl group, C ₃ ~C ₆₀ cycloalkyl group, heterocycloalkyl group having 3 to 60 nuclear atoms, C ₃ ~C ₆₀ cycloalkenyl group, heterocycloalkenyl group having 3 to 60 nuclear atoms, C ₆ ~C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~C ₆₀ alkyloxy group, C ₆ ~C ₆₀ aryloxy group, C ₁ ~C ₆₀ 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 Substituted or unsubstituted with one or more substituents selected from the group consisting of arylphosphine oxide groups and C ₆ to C ₆₀ arylamine groups, 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.

The organic layer including the organic compound may be at least one selected from the group consisting of a light-emitting layer, an electron transport layer, and an electron transport auxiliary layer.

The compound of the present invention can be used as an organic layer material of an organic electroluminescent device because it has excellent heat resistance, electron transport and injection ability, luminescence ability, 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, 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.
FIG. 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 present invention provides a novel compound that can be used as a high-efficiency light-emitting layer material (specifically, a host) or an electron transport layer material or an electron transport auxiliary layer material of an organic electroluminescent device, having electron injection and transport ability, luminescence ability, electrochemical stability, thermal stability, etc.

Specifically, the compound represented by the chemical formula 1 according to the present invention includes a structure in which a nitrogen-containing heteroaromatic ring (e.g., azine), which is an electron withdrawing group (EWG) with high electron absorption, is introduced into a fluorene, xanthene and/or thioxanthene-containing core through a linker group (L), such as a fluorene moiety, a naphtho benzo moiety, a spiro(fluorene-fluorene) moiety, a spiro(xanthene-fluorene) moiety, a spiro(thioxanthene-fluorene) moiety, etc., and the linker group (L) is substituted with an alkyl group.

The compound of the above chemical formula 1 has a tilted structure by substituting the linker group (L) with an alkyl group, which increases the steric hindrance phenomenon and thus can increase efficiency. In addition, the compound of the above chemical formula 1 can also improve thermal stability by increasing the glass transition temperature (Tg).

In addition, since the compound of the above chemical formula 1 includes a nitrogen-containing heteroaromatic ring represented by chemical formula 7 or 8, the nitrogen-containing heteroaromatic ring is an electron-withdrawing group (EWG) with high electron absorption, and thus the electron transfer rate is improved, so that electron injection and transport properties can be improved.

In addition, since the compound of the above chemical formula 1 has high triplet energy, it can prevent excitons generated in the light-emitting layer from diffusing (moving) to the adjacent electron transport layer or hole transport layer. Therefore, the compound of the above chemical formula 1 can be used as a material for an auxiliary layer (hereinafter, 'electron transport auxiliary layer') interposed between the light-emitting layer and the electron transport layer. In particular, when the compound of the above chemical formula 1 is included in an organic electroluminescent device as a material for an electron transport auxiliary layer, the number of excitons contributing to light emission in the light-emitting layer increases, so that the luminescence 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. In addition, since the organic electroluminescent device including the compound of the above chemical formula 1 can be driven at a low voltage, the lifespan of the device can be improved. The performance of a full-color organic light-emitting panel to which such an organic electroluminescent device is applied can also be maximized.

As described above, the compound represented by the chemical formula 1 according to the present invention has excellent luminescence ability, electron injection and transport ability. Therefore, the compound of the present invention can be used as an organic layer of an organic electroluminescent device, preferably as a luminescent layer material (a blue, green and/or red phosphorescent host material), an electron transport layer/injection layer material, an electron transport auxiliary layer material, a hole transport layer/injection layer material, a luminescent auxiliary layer material, a life-span improving layer material, and more preferably as a luminescent layer material (a blue, green and/or red phosphorescent host material), an electron transport layer material, an electron transport auxiliary layer material. An organic electroluminescent device including the compound of the present invention can have significantly 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.

In the compound represented by the above chemical formula 1, L is a divalent linker connecting substituents A1 and A2, and is a C ₆ to C ₃₀ arylene group substituted with one or more R _{1 s} , and specifically, may be a C ₆ to C ₁₈ arylene group substituted with one or more R _{1 s} .

In one example, the L may be a linker group selected from the group consisting of the following linker groups L1-1 to L1-3.

In the above chemical formulas L1-1 to L1-3,

m ₁ to m ₃ are 0 or 1, respectively, but 1≤m ₁ +m ₂ ≤2 and 1≤m ₁ +m ₂ +m ₃ ≤3.

Examples of the linker groups represented by the above linker groups L1-1 to L1-3 include, but are not limited to, the following linker groups L2-1 to L2-14. However, since the linker groups L2-1 to L2-14 connect between the substituents A1 and A2, the steric hindrance phenomenon in the compound of chemical formula 1 may increase, thereby increasing efficiency, and the glass transition temperature (Tg) may also increase, thereby improving thermal stability.

In the above linker groups L2-1 to L2-14,

* means a part that is bonded with A1 and A2 of the above chemical formula 1,

Plural R ₁ are the same or different, and R ₁ is as defined in chemical formula 1.

Specifically, examples of the linker groups represented by the linker groups L1-1 to L1-3 include, but are not limited to, the following linker groups L3-1 to L3-46.

In the above linker groups L3-1 to L3-46,

* means a part that is bonded with A1 and A2 of the above chemical formula 1,

Plural R ₁ are the same or different, and R ₁ is as defined in chemical formula 1.

In the above chemical formula 1, when there are plural R ₁ s, they are the same or different from each other, and R ₁ is a C ₁ to C ₂₀ alkyl group, and specifically, may be a C ₁ to C ₆ alkyl group. According to an example, the R ₁ may be selected from the group consisting of a methyl group, an ethyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, and a t-butyl group.

In the above chemical formula 1, A1 is a substituent represented by any one of the following chemical formulas 2 to 6. The substituents of the chemical formulas 2 to 6 are substituents having electron donating group (EDG) characteristics with high electron donating ability, and by bonding with substituent A2, which is an electron withdrawing group (EWG) with high electron absorbing ability, through the linker group L, the compound of the above chemical formula 1 has bipolar characteristics throughout the molecule, and thus the bonding force between holes and electrons can be enhanced.

In the above chemical formulas 2 to 6,

* means a part that is bonded with L of the above chemical formula 1,

X ₁ is selected from the group consisting of C(G ₁ )(G ₂ ), S and O,

X ₂ , X ₃ and X ₄ are S or O, respectively.

Also, in the chemical formulas 2 to 6, a and f are each integers from 0 to 7, b, d, e and g are each integers from 0 to 8, and c is an integer from 0 to 4.

Here, when a is 0, it means that hydrogen is not substituted with substituent R ₂ , when b is 0, it means that hydrogen is not substituted with substituent R ₃ , when c is 0, it means that hydrogen is not substituted with substituent R ₄ , when d is 0, it means that hydrogen is not substituted with substituent R ₅ , when e is 0, it means that hydrogen is not substituted with substituent R ₆ , when f is 0, it means that hydrogen is not substituted with substituent R ₇ , and when g is 0, it means that hydrogen is not substituted with substituent R ₈ . Meanwhile, when a and f are each an integer of 1 to 7, b, d, e and g are each an integer of 1 to 8, and c is an integer of 1 to 4, 1 or more R ₂ to R ₈ are the same or different from each other and each independently represent deuterium, a halogen group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a C ₁ to C ₆₀ alkyl group, a C ₂ to C ₆₀ alkenyl group, a C ₂ to C ₆₀ alkynyl group, a C ₃ to C 60 cycloalkyl group, a heterocycloalkyl group having 3 to ₆₀ nuclear atoms, a C _{3 to C 60 cycloalkenyl group, and a C 3} to C ₆₀ cycloalkenyl group having 3 to 60 nuclear atoms. A heterocycloalkenyl group, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to ₆₀ carbon atoms, an alkyloxy group having ₁ to 60 carbon atoms, an aryloxy group having ₆ to ₆₀ carbon atoms, an alkylsilyl group having ₁ to ₆₀ carbon atoms, an arylsilyl group having ₆ to ₆₀ carbon atoms, an alkylboron group having ₁ to ₄₀ carbon atoms, an arylborone group having ₆ to ₆₀ carbon atoms, an arylphosphine group having ₆ to ₆₀ carbon atoms, an arylphosphine oxide group having ₆ to ₆₀ carbon atoms, and an arylamine group having ₆ to ₆₀ carbon atoms, or an adjacent group (e.g., R ₂ -R ₂ , R ₃ -R ₃ , R ₄ -R ₄ , R ₅ -R ₅ , R ₆ -R ₆ , R ₇ -R ₇ , R ₈ -R ₈ ) can be combined with each other to form a condensed ring. Here, the heterocycloalkyl group and the heteroaryl group can each include one or more heteroatoms selected from the group consisting of N, S, O and Se, and the condensed ring can be one or more selected from the group consisting of a condensed aliphatic ring of C ₃ to C ₃₀ , a condensed aromatic ring of C ₆ to C ₆₀ and a condensed heteroaromatic ring of 5 to 60 members.

In one example, R ₂ to R ₈ are the same or different from each other, and can each independently be selected from the group consisting of hydrogen, deuterium, a C ₁ to C ₃₀ alkyl group, a C ₂ to C ₃₀ alkenyl group, a C ₂ to C ₃₀ alkynyl group, a C ₆ to C ₃₀ aryl group, and a heteroaryl group having 5 to 30 nuclear atoms.

In the above chemical formulas 2 to 6, G ₁ and G ₂ are the same as or different from each other, and each independently represent hydrogen, deuterium, a halogen group, a hydroxy group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a C ₁ to C ₆₀ alkyl group, a C ₂ to C ₆₀ alkenyl group, a C ₂ to C ₆₀ alkynyl group, a C ₃ to C ₆₀ cycloalkyl group, a heterocycloalkyl group having 3 to 60 nuclear atoms, a C ₃ to C ₆₀ cycloalkenyl group, a heterocycloalkenyl group having 3 to 60 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C It is selected from the group consisting of an alkyloxy group of ₆₀ , an aryloxy group of C ₆ to C ₆₀ , an alkylsilyl group of C ₁ to C ₆₀ , an arylsilyl group of C ₆ to C ₆₀ , an alkylboron group of C ₁ to C 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 , or may be combined with adjacent groups (e.g., G ₁ -G ₂ ) to form a condensed ring. Here, the heterocycloalkyl group and the heteroaryl group may each include one or more heteroatoms selected from the group consisting of N, S, O, and Se, and the condensed ring may be one or more selected from the group consisting of a condensed aliphatic ring of C ₃ to C ₃₀ , a condensed aromatic ring of C ₆ to C ₆₀ , and a condensed heteroaromatic ring of 5 to 60 members.

In one embodiment, G ₁ and G ₂ are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, a C ₁ to C ₃₀ alkyl group, a C ₂ to C ₃₀ alkenyl group, a C ₂ to C ₃₀ alkynyl group, a C ₆ to C ₃₀ aryl group, and a heteroaryl group having 5 to 30 nuclear atoms, or may be bonded to adjacent groups (e.g., G ₁ -G ₂ ) to form a condensed ring.

In the above chemical formulas 2 to 6, ring R is a C ₆ to C ₁₂ monocyclic aromatic ring and a C ₆ to C ₂₀ polycyclic aromatic ring. Here, each ring in the polycyclic aromatic ring may be the same or different. Specifically, examples of ring R may include, but are not limited to, a benzene ring, a naphthalene ring, an anthracene ring, a tetracene ring, a pyrene ring, a phenanthrene ring, a phenalene ring, a benzoanthracene ring, a benzopyrene ring, a triphenylene ring, a chrysene ring, a pentaphene ring, a pentacene ring, and a condensed ring between the two types of rings mentioned above.

In one example, the above A1 may be a substituent selected from the group consisting of the following substituents A1-1 to A1-16.

In the above substituents A1-1 to A1-16,

X ₁ to X ₄ are each independently O or S.

The hydrogen of the above substituents A1-1 to A1-16 may be substituted with one or more substituents such as deuterium (D), halogen, cyano group, nitro group, C ₁ to C ₁₂ alkyl group, C ₆ to C ₁₀ aryl group, and heteroaryl group having 5 to 9 nuclear atoms.

In the above chemical formula 1, A2 is a substituent represented by the following chemical formula 7 or 8. The substituents represented by the chemical formulas 7 and 8 are electron withdrawing groups (EWGs) with high electron absorption, and have excellent electron injection and transport properties, so that the electron transfer rate of the compound can be improved.

In the above chemical formulas 7 and 8,

Y ₁ to Y ₃ are each independently C(G ₃ ) or N, provided that at least one of Y ₁ to Y ₃ is N,

One of Y ₄ to Y ₇ is C (carbon) and is connected to L, and the remaining Y ₄ to Y ₇ and Y ₈ to Y ₁₁ are the same or different from each other and are each independently C (G ₄ ) or N, provided that at least one of Y ₄ to Y ₁₁ is N,

Z ₁ is S or O,

G ₃ and G ₄ are the same or different from each other, and each independently represent hydrogen, deuterium, a halogen group, a hydroxy group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a C ₁ to C ₆₀ alkyl group, a C ₂ to C ₆₀ alkenyl group, a C ₂ to C ₆₀ alkynyl group, a C ₃ to C ₆₀ cycloalkyl group, a heterocycloalkyl group having 3 to 60 nuclear atoms, a C ₃ to C ₆₀ cycloalkenyl group, a heterocycloalkenyl group having 3 to 60 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₆₀ It is selected from the group consisting of an alkyloxy group, a C ₆ ~C ₆₀ aryloxy group, a C ₁ ~C ₆₀ alkylsilyl group, a C ₆ ~C ₆₀ arylsilyl group, a C ₁ ~C ₄₀ alkylboron group, a C ₆ ~C ₆₀ arylboron group, a C ₆ ~C ₆₀ arylphosphine group, a C ₆ ~C ₆₀ arylphosphine oxide group, and a C ₆ ~C ₆₀ arylamine group, and specifically, it can be selected from the group consisting of hydrogen, deuterium, a C ₁ ~C ₃₀ alkyl group, a C ₂ ~C ₃₀ alkenyl group, a C ₂ ~C ₃₀ alkynyl group, a C ₆ ~C ₃₀ aryl group, and a heteroaryl group having 5 to 30 nuclear atoms.

In one example, the above A2 may be a substituent selected from the group consisting of the following substituents A2-1 to A2-8.

In the above substituents A2-1 to A2-8,

Ar ₁ and Ar ₂ , Z ₁ , G ₃ and G ₄ are as defined in chemical formulas 7 and 8, respectively,

h is an integer from 0 to 4,

When G ₄ is plural, they are either identical or different.

In _the above chemical formula 1, the arylene group of _L , the alkyl group and cycloalkyl group of R ₁ , _the hydrazino group, hydrazono group, alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, cycloalkenyl group, heterocycloalkenyl 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 R 2 to R 8, G 1 to G 4 are each independently deuterium, halogen group, hydroxy group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C ₁ to C ₆₀ Alkyl group, C ₂ ~C ₆₀ alkenyl group, C ₂ ~C ₆₀ alkynyl group, C ₃ ~C ₆₀ cycloalkyl group, heterocycloalkyl group having 3 to 60 nuclear atoms, C ₃ ~C ₆₀ cycloalkenyl group, heterocycloalkenyl group having 3 to 60 nuclear atoms, C ₆ ~C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~C ₆₀ alkyloxy group, C ₆ ~C ₆₀ aryloxy group, C ₁ ~C ₆₀ alkylsilyl group, C ₆ ~C ₆₀ arylsilyl group, C ₁ ~C ₄₀ alkylboron group, C ₆ ~C ₆₀ arylborone group, C ₆ ~C ₆₀ It is substituted or unsubstituted with one or more substituents selected from the group consisting of an arylphosphine group, a C ₆ to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group. In this case, when there are multiple substituents, they are the same or different from each other.

Specifically, _the arylene group of L, the alkyl group and cycloalkyl group of R ₁ , _the hydrazino _group , hydrazono group, alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, cycloalkenyl group, heterocycloalkenyl 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 may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano group, nitro group, C ₁ to C ₂₀ alkyl group, C ₆ to C ₃₀ aryl group, and heteroaryl group having 5 to 30 nuclear atoms, In this case, when there are multiple substituents, they are the same or different.

The compound represented by the above chemical formula 1 can be embodied as a compound represented by any one of the following chemical formulas 9 to 18, but is not limited thereto.

In the above chemical formulas 9 to 18,

m is an integer from 1 to 4,

n is an integer from 1 to 3,

R ₁ to R ₈ , X ₁ to X ₄ , Y ₁ to Y ₁₁ , G ring, and a to g are each as defined in Chemical Formula 1.

The compound represented by the chemical formula 1 according to the present invention described above can be further specified as the following exemplary compounds, for example, compounds Inv 1 to Inv 1104, but is not limited thereto.

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.

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, triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl.

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 not only mono- but also polyarylsilyl such as 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, "arylphosphinyl group" in the present invention means a phosphine group substituted with a monoaryl or diaryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylphosphinyl groups.

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, “heteroarylamine” means an amine substituted with a heteroaryl having 5 to 60 nuclear atoms, and includes not only mono- but also di-heteroarylamine.

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

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

Organic electroluminescent devices

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

Figures 1 to 3 are cross-sectional views schematically showing organic electroluminescent devices according to the first to third embodiments of the present invention.

Hereinafter, organic electroluminescent devices according to the first to third embodiments of the present invention will be described in detail with reference to FIGS. 1 to 3.

As illustrated in FIGS. 1 to 3, 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, and at least one of the one or more organic layers includes a compound represented by the chemical formula 1. At this time, the compound may be used alone, or two or more may be mixed and used.

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

According to an 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 layer, and an electron injection layer, and the light-emitting layer includes a host and a dopant, and the host may be a compound represented by the chemical formula 1. In this case, the light-emitting layer of the present invention may include a compound known in the art as a second host in addition to the compound of the chemical formula 1.

In the present invention, the content of the host may be about 70 to 99.9 wt% based on the total amount of the light-emitting layer, and the content of the dopant may be about 0.1 to 30 wt% based on the total amount of the light-emitting layer.

When the compound represented by the above chemical formula 1 is included as a light-emitting layer material of an organic electroluminescent device, preferably as a blue, green, or red phosphorescent host material, the bonding force between holes and electrons in the light-emitting layer increases, thereby improving the efficiency (luminescent efficiency and power efficiency), lifespan, brightness, and driving voltage of the organic electroluminescent device. Specifically, the compound represented by the above chemical formula 1 is preferably included in the organic electroluminescent device as a green and/or red phosphorescent host, fluorescent host, or dopant material. In particular, the compound represented by the chemical formula 1 of the present invention is preferably a green phosphorescent exciplex N-type host material of a light-emitting layer having high efficiency.

According to another example, the organic material layer of one or more layers may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and may optionally further include an electron transport auxiliary layer. The electron transport layer includes a compound represented by the above chemical formula 1. In this case, the compound represented by the above chemical formula 1 is included in the organic electroluminescent device as an electron transport layer material. In such an organic electroluminescent device, electrons can be easily injected from the cathode or the electron injection layer to the electron transport layer due to the compound 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 a compound represented by the chemical formula 1. At this time, the compound represented by the chemical formula 1 is included in an organic electroluminescent device as an electron transport auxiliary layer material. At this time, the compound 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 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 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 the electrode using materials and methods known in the art, except that at least one of the organic layers (300) [e.g., the light-emitting layer (330), the electron transport layer (340), or the electron transport auxiliary layer (360)] includes a compound represented by the chemical formula 1.

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 Core1

2-Bromo-9,9-dimethyl-9H-fluorene (100 g, 366 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (111.55 g, 439.2 mmol), Pd(dppf)Cl ₂ (8.03 g, 10.98 mmol), and KOAc (107.8 g, 1098.2 mmol) were added to 1,4-Dioxane (800 ml) and heated under reflux for 12 h. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent of the filtered organic layer, the target compound Core 1 (95.2 g, yield 81%) was obtained using column chromatography.

¹ H-NMR: δ 1.57 (s, 12H), 1.65 (m, 6H), 7.05 (t, 1H), 7.22 (m, 2H), 7.43 (m, 2H), 7.92 (m, 2H)

[Examples 2-23] Synthesis of Core2-23

Instead of 2-bromo-9,9-dimethyl-9H-fluorene used in Preparation Example 1, 3-bromo-9,9-dimethyl-9H-fluorene, 4-bromo-9,9-dimethyl-9H-fluorene, 2-bromo-9,9-phenyl-9H-fluorene, 3-bromo-9,9-phenyl-9H-fluorene, 4-bromo-9,9-phenyl-9H-fluorene, 2-bromo-9,9'-spirobi[fluorene], 3-bromo-9,9'-spirobi[fluorene], 4-bromo-9,9'-spirobi[fluorene], 2'-bromospiro[cyclohexane-1,9'-fluorene], 3'-bromospiro[cyclohexane-1,9'-fluorene], 4'-bromospiro[cyclohexane-1,9'-fluorene], 2-bromospiro[benzo[b]fluorene-11,9'-xanthene], 10-bromonaphtho[2,1-b]benzofuran, 3-bromonaphtho[2,3-b]benzofuran, 2-bromonaphtho[2,3-b]benzofuran, 9-bromospiro[benzo[c]fluorene-7,9'-xanthene], 2-bromospiro[benzo[b]fluorene-11,9'-xanthene], 3'-bromospiro[benzo[c]fluorene-7,9'-xanthene], 3'-bromospiro[benzo[b]fluorene-11,9'-xanthene], 9-bromospiro[benzo[de]anthracene-7,9'-xanthene], The following target compounds, Core2 to Core21, were prepared in the same manner as in Preparation Example 1, except that 9-bromo-7,7-dimethyl-7H-benzo[c]fluorene and 2-bromo-11,11-dimethyl-11H-benzo[b]fluorene were used, respectively.

[Synthesis Example 1] Synthesis of compound Inv 5

Core1 (5.0 g, 15.61 mmol), 2-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (5.64 g, 13.01 mmol), Pd(OAc) ₂ (0.08 g, 0.39 mmol), Cs ₂ CO ₃ (8.4 g, 26 mmol), and Xphos (0.62 g, 1.3 mmol) synthesized in [Preparation Example 1] were added to a mixed solvent of toluene (100 ml), EtOH (25 ml), and H ₂ O (25 ml), and heated under reflux for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent from the filtered organic layer, compound Inv 5 (5.0 g, yield 65%) was obtained using column chromatography.

[LCMS]: 592

[Synthesis Example 2] Synthesis of compound Inv 40

Except that 4-(3'-chloro-4'-methyl-[1,1'-biphenyl]-3-yl)-2-phenylbenzo[4,5]thieno[3,2-d]pyrimidine (6.0 g 13.01 mmol) was used instead of 2-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine used in [Synthetic Example 1], the same procedure as in [Synthetic Example 1] was performed to obtain compound Inv 40 (5.2 g, yield 64%).

[LCMS]: 621

[Synthesis Example 3] Synthesis of compound Inv 56

Compound Inv 56 (5.3 g, yield 67%) was obtained by performing the same procedure as in [Synthesis Example 1], except that Core2 was used instead of Core1 in [Synthesis Example 1], and 2-(5'-chloro-2',6-dimethyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine.

[LCMS]: 606

[Synthesis Example 4] Synthesis of compound Inv 81

Compound Inv 81 (5.5 g, yield 63%) was obtained by performing the same procedure as in [Synthesis Example 1], except that Core2 was used instead of Core1 in [Synthesis Example 1], and 2-(3''-chloro-6-methyl-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(4'-chloro-2'-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine.

[LCMS]: 668

[Synthesis Example 5] Synthesis of compound Inv 117

Compound Inv 117 (5.6 g, yield 64%) was obtained by performing the same procedure as in [Synthesis Example 1], except that Core3 was used instead of Core1 in [Synthesis Example 1], and 4-([1,1'-biphenyl]-4-yl)-6-(3'-chloro-2-methyl-[1,1'-biphenyl]-4-yl)-2-phenylpyrimidine (6.6 g 13.01 mmol) was used instead of 2-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine.

[LCMS]: 667

[Synthesis Example 6] Synthesis of compound Inv 138

Compound Inv 138 (6.4 g, yield 72%) was obtained by performing the same procedure as in [Synthesis Example 1], except that Core3 was used instead of Core1 in [Synthesis Example 1] and 4-(5'-chloro-2'-methyl-[1,1'-biphenyl]-3-yl)-2-phenylbenzofuro[3,2-d]pyrimidine (6.69 g 13.14 mmol) was used instead of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine.

[LCMS]: 803

[Synthesis Example 7] Synthesis of compound In 161

Compound Inv 161 (4.8 g, yield 65%) was obtained by performing the same procedure as in [Synthesis Example 1], except that Core4 was used instead of Core1 in [Synthesis Example 1], and 4-([1,1'-biphenyl]-4-yl)-6-(4'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine.

[LCMS]: 792

[Synthesis Example 8] Synthesis of compound Inv 197

Compound Inv 197 (4.6 g, yield 68%) was obtained by performing the same process as in [Synthesis Example 1], except that Core5 (5.0 g, 11.25 mmol) was used instead of Core1 used in [Synthesis Example 1].

[LCMS]: 716

[Synthesis Example 9] Synthesis of compound Inv 232

Except that 4-(3'-chloro-4'-methyl-[1,1'-biphenyl]-3-yl)-2-phenylbenzo[4,5]thieno[3,2-d]pyrimidine (4.35 g 93.76 mmol) was used instead of 2-(4'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine used in [Synthetic Example 8], the same process as in [Synthetic Example 8] was performed to obtain compound Inv 232 (4.5 g, yield 64%).

[LCMS]: 745

[Synthesis Example 10] Synthesis of compound Inv 254

Compound Inv 254 (6.7 g, yield 64%) was obtained by performing the same procedure as in [Synthesis Example 1], except that Core6 was used instead of Core1 in [Synthesis Example 1], and 2-(4'-chloro-2'-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine.

[LCMS]: 716

[Synthesis Example 11] Synthesis of compound Inv 302

Inv 302 (4.5 g, yield 67%) was obtained by performing the same procedure as in [Synthesis Example 1], except that Core7 was used instead of Core1 in [Synthesis Example 1], and 2-(4'-chloro-2'-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine.

[LCMS]: 714

[Synthesis Example 12] Synthesis of compound Inv372

Compound Inv 372 (6.3 g, yield 71%) was obtained by performing the same procedure as in [Synthesis Example 1], except that Core8 was used instead of Core1 in [Synthesis Example 1], and 2-(3''-chloro-6,6'-dimethyl-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine.

[LCMS]: 805

[Synthesis Example 13] Synthesis of compound Inv 393

Compound Inv 393 (4.5 g, yield 67%) was obtained by performing the same procedure as in [Synthesis Example 1], except that Core9 was used instead of Core1 used in [Synthesis Example 1], and 2-(3'-chloro-2-methyl-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (4.1 g 9.42 mmol) was used instead of 2-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine.

[LCMS]: 714

[Synthesis Example 14] Synthesis of compound Inv 457

Except that Core10 was used instead of Core1 used in [Synthetic Example 1], and 2-([1,1'-biphenyl]-4-yl)-4-(4'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazine (5.9 g 11.56 mmol), the same procedure as in [Synthetic Example 1] was performed to obtain compound Inv 457 (5.3 g, yield 65%).

[LCMS]: 708

[Synthesis Example 15] Synthesis of compound Inv 515

Compound Inv 515 (5.4 g, yield 66%) was obtained by performing the same procedure as in [Synthesis Example 1], except that Core11 was used instead of Core1 used in [Synthesis Example 1], and 2-(3''-chloro-4''-methyl-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine.

[LCMS]: 708

[Synthesis Example 16] Synthesis of compound Inv 566

Compound Inv 566 (4.9 g, yield 64%) was obtained by performing the same procedure as in [Synthesis Example 1], except that Core 12 was used instead of Core 1 used in [Synthesis Example 1], and 4-(5'-chloro-2'-methyl-[1,1'-biphenyl]-3-yl)-2-phenylbenzo[4,5]thieno[3,2-d]pyrimidine (5.35 g 11.56 mmol) was used instead of 2-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine.

[LCMS]: 661

[Synthesis Example 17] Synthesis of compound Inv 609

Compound Inv 609 (5.5 g, yield 65%) was obtained by performing the same procedure as in [Synthesis Example 1], except that Core13 was used instead of Core1 used in [Synthesis Example 1], and 2-(3''-chloro-6-methyl-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine.

[LCMS]: 692

[Synthesis Example 18] Synthesis of compound Inv 644

[Synthetic Example 1] was performed in the same manner as in [Synthetic Example 1], except that Core14 was used instead of Core1 and 4-([1,1'-biphenyl]-4-yl)-6-(4'-chloro-2',6-dimethyl-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine (6.33 g 12.1 mmol) was used instead of 2-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine, to obtain compound Inv 644 (5.7 g, yield 67%).

[LCMS]: 705

[Synthesis Example 19] Synthesis of compound Inv 708

[Synthetic Example 1] was performed in the same manner as in [Synthetic Example 1], except that Core15 was used instead of Core1 and 2-(3''-chloro-6,6'-dimethyl-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (6.34 g 12.1 mmol) was used instead of 2-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine, thereby obtaining compound Inv 708 (5.4 g, yield 63%).

[LCMS]: 706

[Synthesis Example 20] Synthesis of compound Inv 761

Compound Inv 761 (5.0 g, yield 66%) was obtained by performing the same procedure as in [Synthesis Example 1], except that Core16 was used instead of Core1 used in [Synthesis Example 1], and 4-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-2-phenylbenzofuro[3,2-d]pyrimidine (5.4 g 12.1 mmol) was used instead of 2-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine.

[LCMS]: 629

[Synthesis Example 21] Synthesis of compound Inv 773

Compound Inv 773 (4.2 g, yield 66%) was obtained by performing the same process as in [Synthesis Example 1], except that Core 17 (5.0 g 9.83 mmol) was used instead of Core 1 used in [Synthesis Example 1].

[LCMS]: 780

[Synthesis Example 22] Synthesis of compound Inv 779

Except that 2-(3'-chloro-4'-methyl-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (3.55 g 8.19 mmol) was used instead of 2-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine used in [Synthetic Example 21], the same process as in [Synthetic Example 21] was performed to obtain compound Inv 779 (4.0 g, yield 62%).

[LCMS]: 780

[Synthesis Example 23] Synthesis of compound Inv 822

Compound Inv 822 (4.2 g, yield 66%) was obtained by performing the same procedure as in [Synthesis Example 1], except that Core18 was used instead of Core1 used in [Synthesis Example 1], and 2-(5'-chloro-2'-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine.

[LCMS]: 780

[Synthesis Example 24] Synthesis of compound Inv 828

Compound Inv 828 (4.3 g, yield 66%) was obtained by performing the same procedure as in [Synthesis Example 1], except that Core18 was used instead of Core1 used in [Synthesis Example 1], and 2-(5'-chloro-2,2'-dimethyl-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine.

[LCMS]: 794

[Synthesis Example 25] Synthesis of compound Inv 871

Compound Inv 871 (4.3 g, yield 67%) was obtained by performing the same procedure as in [Synthesis Example 1], except that Core19 was used instead of Core1 used in [Synthesis Example 1], and 2-(3'-chloro-4'-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (3.55 g 8.19 mmol) was used instead of 2-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine.

[LCMS]: 780

[Synthesis Example 26] Synthesis of compound Inv 887

Compound Inv 887 (4.7 g, yield 67%) was obtained by performing the same procedure as in [Synthesis Example 1], except that Core19 was used instead of Core1 used in [Synthesis Example 1], and 4-([1,1'-biphenyl]-4-yl)-6-(3'-chloro-4'-methyl-[1,1'-biphenyl]-4-yl)-2-phenylpyrimidine (4.17 g 8.19 mmol) was used instead of 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine.

[LCMS]: 856

[Synthesis Example 27] Synthesis of compound Inv 930

Inv 930 (4.5 g, yield 64%) was obtained by performing the same procedure as in [Synthesis Example 1], except that Core20 was used instead of Core1 used in [Synthesis Example 1], and 4-([1,1'-biphenyl]-4-yl)-6-(4'-chloro-2'-methyl-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine (4.17 g 8.19 mmol) was used instead of 2-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine.

[LCMS]: 856

[Synthesis Example 28] Synthesis of compound Inv 949

Compound Inv 949 (4.3 g, yield 65%) was obtained by performing the same procedure as in [Synthesis Example 1], except that Core20 was used instead of Core1 in [Synthesis Example 1], and 4-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-2-phenylbenzo[4,5]thieno[3,2-d]pyrimidine (3.79 g 8.19 mmol) was used instead of 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine.

[LCMS]: 810

[Synthesis Example 29] Synthesis of compound Inv 965

Compound Inv 965 (4.7 g, yield 65%) was obtained by performing the same process as in [Synthesis Example 1], except that Core22 (5.0 g 13.5 mmol) was used instead of Core1 used in [Synthesis Example 1].

[LCMS]: 642

[Synthesis Example 30] Synthesis of compound Inv 1000

[Synthetic Example 1] was performed in the same manner as in [Synthetic Example 1], except that Core23 was used instead of Core1 and 4-(3'-chloro-4'-methyl-[1,1'-biphenyl]-3-yl)-2-phenylbenzo[4,5]thieno[3,2-d]pyrimidine (5.18 g 11.25 mmol) was used instead of 2-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine, thereby obtaining compound Inv 1000 (4.8 g, yield 64%).

[LCMS]: 671

[Synthesis Example 31] Synthesis of compound Inv 1061

Compound Inv 1061 (4.2 g, yield 65%) was obtained by performing the same process as in [Synthesis Example 1], except that Core21 (5.0 g, 9.83 mmol) was used instead of Core1 used in [Synthesis Example 1].

[LCMS]: 780

[Synthesis Example 32] Synthesis of compound Inv 1061

Except that 4-([1,1'-biphenyl]-4-yl)-6-(3'-chloro-4'-methyl-[1,1'-biphenyl]-4-yl)-2-phenylpyrimidine (4.17 g 8.19 mmol) was used instead of 2-(3'-chloro-6-methyl-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine used in [Synthesis Example 31], the same process as in [Synthesis Example 31] was performed to obtain the target compound, compound Inv 1061 (4.6 g, yield 66%).

[LCMS]: 856

[Example 1] Fabrication of a green organic EL device

In Synthesis Example 2, compound Inv 40 was purified to high purity by sublimation according to a commonly known method, and then a green organic EL device was manufactured according to the following process.

First, a glass substrate coated with a 1,500 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning, 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.

An organic EL device was fabricated by stacking m-MTDATA (60 nm)/TCTA (80 nm)/compound Inv 40 + 10% Ir(ppy) ₃ (30 nm)/BCP (10 nm)/Alq ₃ (30 nm)/LiF (1 nm)/Al (200 nm) in this order on the prepared ITO transparent electrode. The structures of m-MTDATA, TCTA, Ir(ppy) ₃ , and BCP used here are as follows, respectively.

[Examples 2 to 32]

A green organic EL device was manufactured in the same manner as in Example 1, except that the compounds described in Table 1 were used instead of the compound Inv 40 used as a light-emitting host material in forming the light-emitting layer in Example 1.

[Comparative Examples 1-9] Fabrication of Green Organic EL Devices

Green organic EL devices of Comparative Examples 1 to 9 were manufactured using the same process as in Example 1, except that CBP and the following compounds A to H were used instead of the compound Inv 40 used as a light-emitting host material in forming the light-emitting layer in Example 1. The structures of CBP and compounds A to H used here are as follows, respectively.

[Evaluation Example 1]

For each green organic EL device manufactured in Examples 1 to 32 and Comparative Examples 1 to 9, the driving voltage and current efficiency at a current density of 10 mA/cm2 were measured, and the results are shown in Table 1 below.

sample Host Driving voltage (V) Current efficiency (cd/A) Example 1 Inv 40 3.9 65.4 Example 2 Inv 56 3.6 66.2 Example 3 Inv 811 3.7 64.5 Example 4 Inv 117 3.9 66.9 Example 5 Inv 138 3.8 64.2 Example 6 Inv 197 3.8 66.4 Example 7 Inv 232 3.7 61.1 Example 8 Inv 254 3.9 62.8 Example 9 Inv 302 3.8 62.2 Example 10 Inv 393 4.2 61.4 Example 11 Inv 457 3.9 61.9 Example 12 Inv 566 4.2 60.6 Example 13 Inv 609 4.5 59.7 Example 14 Inv 644 3.9 58.4 Example 15 Inv 708 4.1 59.2 Example 16 Inv 773 4.2 60.2 Example 17 Inv 779 4.0 59.4 Example 18 Inv 822 4.3 58.8 Example 19 Inv 828 4.1 58.6 Example 20 Inv 887 3.8 62.2 Example 21 Inv 930 4.0 63.3 Example 22 Inv 949 4.2 61.4 Example 23 Inv 965 3.9 61.9 Example 24 Inv 1079 4.1 62.8 Example 25 Inv 5 3.8 64.2 Example 26 Inv 161 4.0 68.3 Example 27 Inv 372 4.0 63.3 Example 28 Inv 515 4.1 62.8 Example 29 Inv 761 4.1 64.8 Example 30 Inv 871 4.2 63.2 Example 31 Inv 1000 4.1 62.8 Example 32 Inv 1061 4.3 62.2 Comparative Example 1 CBP 5.6 42.6 Comparative Example 2 A 4.8 52.3 Comparative Example 3 B 4.7 55.8 Comparative Example 4 C 4.6 56.6 Comparative Example 5 D 4.7 54.2 Comparative Example 6 E 4.7 56.6 Comparative Example 7 F 4.8 57.6 Comparative Example 8 G 4.9 58.6 Comparative Example 9 H 4.8 55.6

As shown in Table 1 above, the green organic EL devices of Examples 1 to 32, in which compounds Inv 40 to Inv 1061 according to the present invention were applied as host materials of the light-emitting layer, were found to exhibit superior performance in terms of efficiency and driving voltage, compared to the green organic EL devices of Comparative Example 1, in which conventional CBP was used, and Comparative Examples 2 to 9, in which compounds A to H having a linker group non-substituted with a methyl group were used as host materials of the light-emitting layer, respectively.

[Example 33] Fabrication of a blue organic electroluminescent device

After the compound Inv 5 synthesized in Synthesis Example 1 was purified to high purity by sublimation according to a commonly known method, a blue organic electroluminescent device was manufactured as follows.

First, a glass substrate coated with a 1,500 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 DS-205 (Doosan Electronics Co., Ltd., 80 nm)/NPB (15 nm)/ADN + 5% DS-405 (Doosan Electronics Co., Ltd., 30 nm)/compound Inv 5 (30 nm)/LiF (1 nm)/Al (200 nm) in that order. The structures of NPB and ADN used here are as follows.

[Examples 34 to 42]

A blue organic EL device was manufactured in the same manner as in Example 33, except that the compounds described in Table 2 were used instead of the compound Inv 5 used as the electron transport layer material in forming the electron transport layer in Example 33.

[Comparative Example 10] Fabrication of a Blue Organic Electroluminescent Device

A blue organic electroluminescent device was manufactured in the same manner as in Example 33, except that Alq ₃ was deposited instead of the compound Inv 5 used as an electron transport layer material when forming the electron transport layer in Example 33. The structure of Alq ₃ used here is as follows.

[Evaluation Example 2]

For each of the blue organic electroluminescent devices manufactured in Examples 33 to 42 and Comparative Example 10, the driving voltage, current efficiency, and luminescence peak at a current density of 10 mA/cm2 were measured, and the results are shown in Table 2 below.

sample electron transport layer Driving voltage (V) EL peak (nm) Current efficiency (cd/A) Example 33 Inv 5 4.0 458 7.0 Example 34 Inv 81 4.1 459 7.0 Example 35 Inv 197 3.8 459 6.9 Example 36 Inv 372 3.9 459 7.0 Example 37 Inv 515 3.8 459 7.1 Example 38 Inv 644 3.7 458 7.1 Example 39 Inv 773 4.2 459 7.1 Example 40 Inv 828 3.8 459 7.2 Example 41 Inv 949 3.9 458 7.0 Example 42 Inv 965 4.1 459 6.9 Comparative Example 10 Alq ₃ 4.8 460 5.8

As shown in Table 2 above, it was found that the blue organic electroluminescent devices of Examples 33 to 42, in which the compound of the present invention was applied to the electron transport layer, exhibited superior performance in terms of driving voltage, emission peak, and current efficiency, compared to the blue organic electroluminescent device of Comparative Example 10, in which Alq ₃ was used in the electron transport layer.

[Example 43] Fabrication of a blue organic electroluminescent device

After the compound Inv 5 synthesized in Synthesis Example 1 was purified to high purity by sublimation according to a commonly known method, a blue organic electroluminescent device was manufactured as follows.

A glass substrate coated with a 1,500 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning, 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 DS-205 (80 nm) / NPB (15 nm) / ADN + 5% DS-405 (Doosan Electronics Co., Ltd., 30 nm) / compound Inv 5 (30 nm) / Alq ₃ (25 nm) / LiF (1 nm) / Al (200 nm) in that order. The structures of NPB and ADN used here are the same as those described in Example 33, and the structure of Alq ₃ is the same as those described in Comparative Example 2.

[Examples 44 to 74]

A blue organic EL device was manufactured in the same manner as in Example 43, except that the compounds described in Table 3 were used instead of the compound Inv 5 used as the electron transport auxiliary layer material when forming the electron transport auxiliary layer in Example 43.

[Comparative Example 11] Fabrication of a blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 43, except that the compound Inv5 used as the electron transport auxiliary layer material in Example 43 was not used and the electron transport layer material Alq ₃ was deposited at 30 nm instead of 25 nm.

[Evaluation Example 3]

For the organic electroluminescent devices manufactured in Examples 43 to 74 and Comparative Example 11, the driving voltage, emission wavelength, current efficiency, and emission wavelength at a current density of 10 mA/cm2 were measured, and the results are shown in Table 3 below.

sample electron transport auxiliary layer Driving voltage (V) Current efficiency (cd/A) EL peak (nm) Example 43 Inv 5 4.3 6.8 457 Example 44 Inv 40 4.0 7.2 458 Example 45 Inv 56 4.1 7.3 458 Example 46 Inv 811 3.9 7.4 457 Example 47 Inv 117 4.0 7.2 458 Example 48 Inv 138 4.4 7.1 458 Example 49 Inv 161 4.3 7.2 458 Example 50 Inv 197 4.1 7.3 458 Example 51 Inv 232 4.2 7.2 458 Example 52 Inv 254 4.1 7.2 457 Example 53 Inv 302 4.3 7.1 458 Example 54 Inv 372 4.0 7.0 458 Example 55 Inv 393 4.2 7.5 458 Example 56 Inv 457 3.9 7.1 458 Example 57 Inv 515 4.1 7.2 458 Example 58 Inv 566 4.0 7.1 458 Example 59 Inv 609 4.3 7.3 458 Example 60 Inv 644 4.3 7.3 458 Example 61 Inv 708 3.8 7.4 457 Example 62 Inv 761 4.2 7.2 458 Example 63 Inv 773 4.2 6.9 457 Example 64 Inv 779 4.3 7.1 458 Example 65 Inv 822 4.2 7.2 458 Example 66 Inv 828 4.0 7.1 458 Example 67 Inv 871 3.9 7.0 458 Example 68 Inv 887 4.3 7.0 458 Example 69 Inv 930 4.1 7.3 457 Example 70 Inv 949 4.2 7.2 458 Example 71 Inv 965 4.1 7.2 457 Example 72 Inv 1000 4.3 7.1 458 Example 73 Inv 1061 4.1 7.4 457 Example 74 Inv 1079 4.2 7.0 458 Comparative Example 11 - 4.7 5.6 457

As shown in Table 3, it was found that the blue organic electroluminescent devices of Examples 43 to 74, in which the compound according to the present invention was applied to the electron transport auxiliary layer, exhibited superior performance in terms of current efficiency and driving voltage compared to the organic electroluminescent device of Comparative Example 11, which included an electron transport layer made of Alq ₃ without an electron transport auxiliary layer.

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 (9)

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

(In the above chemical formula 1,
L is a linker group selected from the group consisting of the following chemical formulas L1-1 to L1-3,

In the above chemical formulas L1-1 to L1-3,
m ₁ to m ₃ are each 0 or 1, provided that 1≤m ₁ +m ₂ ≤2 and 1≤m ₁ +m ₂ +m ₃ ≤3;
When R ₁ is plural, they are the same or different, and each independently represents an alkyl group of C ₁ to C ₆ ,
A1 is a substituent represented by any one of the following chemical formulas 2 and 4 to 6,
[Chemical Formula 2]

[Chemical Formula 4] [Chemical Formula 5]

[Chemical Formula 6]

In the above chemical formulas 2 and 4 to 6,
X ₁ is selected from the group consisting of C(G ₁ )(G ₂ ), S and O,
X ₂ , X ₃ and X ₄ are S or O respectively,
a and f are integers from 0 to 7,
d, e and g are integers from 0 to 8, respectively.
c is an integer from 0 to 4,
R ₂ and R ₄ to R ₈ are the same or different from each other, and each independently represent hydrogen, deuterium, a halogen group, a hydroxy group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a C ₁ to C ₆₀ alkyl group, a C ₂ to C ₆₀ alkenyl group, a C ₂ to C ₆₀ alkynyl group, a C ₃ to C ₆₀ cycloalkyl group, a heterocycloalkyl group having 3 to 60 nuclear atoms, a C ₃ to C ₆₀ cycloalkenyl group, a heterocycloalkenyl group having 3 to 60 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₆₀ is selected from the group consisting of an alkyloxy group, an aryloxy group having C ₆ to C ₆₀ , an alkylsilyl group having C ₁ to C ₆₀ , an arylsilyl group having C ₆ to C ₆₀ , an alkylboron group having C ₁ to C ₄₀ , an arylboron group having C ₆ to C ₆₀ , an arylphosphine group having C ₆ to C ₆₀ , an arylphosphine oxide group having C ₆ to C ₆₀ , and an arylamine group having C ₆ to C ₆₀ , or may be combined with adjacent groups to form a condensed aromatic ring or a condensed heteroaromatic ring.
G ₁ and G ₂ are the same or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a hydroxyl group, a cyano group, a C ₁ to C ₆₀ alkyl group, and a C ₆ to C ₆₀ aryl group, or may be combined with adjacent groups to form a condensed aromatic ring,
Ring R is a monocyclic aromatic ring of C ₆ to C ₁₂ or a polycyclic aromatic ring of C ₆ to C ₂₀ ,
A2 is a substituent represented by the following chemical formula 7 or 8,
[Chemical Formula 7] [Chemical Formula 8]

In the above chemical formulas 7 and 8,
Y ₁ to Y ₃ are each independently C(G ₃ ) or N, provided that at least one of Y ₁ to Y ₃ is N,
Ar ₁ and Ar ₂ are each an aryl group of C ₆ to C ₁₂ ,
One of Y ₄ to Y ₇ is C and is connected to L, and the remaining Y ₄ to Y ₇ and Y ₈ to Y ₁₁ are the same or different from each other and are each independently C(G ₄ ) or N, provided that at least one of Y ₄ to Y ₁₁ is N,
Z ₁ is S or O,
G ₃ and G ₄ are the same or different from each other, and each independently represent hydrogen, deuterium, a halogen group, a hydroxy group, a cyano group, a nitro group, a C ₁ to C ₆₀ alkyl group, a C ₂ to C ₆₀ alkenyl group, a C ₂ to C ₆₀ alkynyl group, a C ₃ to C ₆₀ cycloalkyl group, a heterocycloalkyl group having 3 to 60 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₆₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₆₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ Selected from the group consisting of an arylborone group, an arylphosphine group having C ₆ to C ₆₀ , an arylphosphine oxide group having C ₆ to C ₆₀ , and an arylamine group having C ₆ to C ₆₀ ,
The alkyl group and aryl group of the above G ₁ and G ₂ , the arylene group of the above L, the alkyl group and cycloalkyl _group of the above R _{1 , the} hydrazino group, hydrazono group, alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, cycloalkenyl group, heterocycloalkenyl 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 G ₃ and G ₄ , 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 are each independently selected from the group consisting of deuterium, halogen group, hydroxy group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C ₁ ~C ₆₀ alkyl group, C ₂ ~C ₆₀ alkenyl group, C ₂ ~C ₆₀ alkynyl group, C ₃ ~C ₆₀ cycloalkyl group, heterocycloalkyl group having 3 to 60 nuclear atoms, C ₃ ~C ₆₀ cycloalkenyl group, heterocycloalkenyl group having 3 to 60 nuclear atoms, C ₆ ~C ₆₀ aryl group, and 5 to 60 nuclear atoms. (Substituted or unsubstituted with one or more substituents _selected from the group consisting of a heteroaryl group, _{a C 1 to} C ₆₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₆₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron 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, wherein when there are multiple substituents, they are the same or different from each other.) In the first paragraph,
An organic compound represented by any one of the following chemical formulae 9, 10, and 13 to 18:
[Chemical Formula 9]

[Chemical Formula 10]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

(In the above chemical formulas 9, 10 and 13 to 18,
m is an integer from 1 to 4,
n is an integer from 1 to 3,
R ₁ to R ₃ , R ₈ , X ₁ to X ₄ , Y ₁ to Y ₁₁ , G ring, and a to g are each as defined in claim 1). delete delete In the first paragraph,
The organic compound wherein A1 is a substituent selected from the group consisting of the following substituents A1-1 to A1-6, A1-8 to A1-16:

(In the above substituents A1-1 to A1-6, A1-8 to A1-16,
X ₁ to X ₄ are each independently O or S). In the first paragraph,
The organic compound wherein A2 is a substituent selected from the group consisting of the following substituents A2-1 to A2-8:

(In the above substituents A2-1 to A2-8,
Ar ₁ and Ar ₂ , Z ₁ , G ₃ and G ₄ are each as defined in Article 1,
h is an integer from 0 to 4,
If G ₄ is plural, they are either the same or different. 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 Inv 1 to Inv 1104:




































































. 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, 2, and 5 to 7. In paragraph 8,
An organic electroluminescent device, wherein the organic layer containing the organic compound is at least one selected from the group consisting of a light-emitting layer, an electron transport layer, and an electron transport auxiliary layer.