KR102423259B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel organic compound excellent in both hole, electron injection and transport ability, light emitting ability, etc. in addition to thermal stability, and an organic electroluminescent device with improved characteristics such as luminous efficiency, driving voltage, and lifespan by including the same in one or more organic material layers will be.

Description

Organic compound and organic electroluminescent device comprising the same

The present invention relates to a novel organic compound that can be used as a material for an organic electroluminescent device and an organic electroluminescent device including the same.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, an exciton is formed, and when the exciton falls to the ground state, light is emitted. In this case, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to their function.

The light emitting material may be divided into blue, green, and red light emitting materials and yellow and orange light emitting materials for realizing a better natural color according to the emission color. In addition, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system may be used as a light emitting material.

The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times compared to the fluorescence, research on phosphorescent host materials as well as the phosphorescent dopant is in progress.

Until now, NPB, BCP, Alq ₃ and the like have been widely known as materials for the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer, and anthracene derivatives have been reported as materials for the light emitting layer. In particular, metal complex compounds containing Ir, such as Firpic, Ir(ppy) ₃ , (acac)Ir(btp) ₂ , which have advantages in terms of efficiency improvement among light emitting layer materials, are blue, green, and red. (red) is used as a phosphorescent dopant material, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.

However, conventional organic material layer materials are advantageous in terms of light emitting properties, but have not been satisfactory in terms of the lifespan of the organic electroluminescent device because the glass transition temperature is low and thermal stability is not very good. Accordingly, there is a demand for the development of an organic layer material having excellent performance.

An object of the present invention is to provide a novel organic compound that can be applied to an organic electroluminescent device, and is excellent in both hole, electron injection and transport ability, light emitting ability, etc. in addition to thermal stability.

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

In order to achieve the above object, the present invention provides a compound represented by the formula (1):

In Formula 1,

X is selected from the group consisting of O, S, N(Ar ₁ ) and C(Ar ₂ )(Ar ₃ ),

Ar ₁ To Ar ₃ Are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ of Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Monoaryl phosphinyl group, C ₆ ~ C ₆₀ Diaryl phosphinyl group and C ₆ ~ C ₆₀ The group consisting of an arylamine group or adjacent substituents (eg, Ar ₂ and Ar ₃ ) may be bonded to each other to form a condensed ring;

Y ₁ To Y ₁₂ Are the same as or different from each other, and each independently C(R ₁ ) or N,

When C(R ₁ ) is a plurality, a plurality of R ₁ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ of 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, heteroatom 5 to 60 Aryl group, 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 Alkyl Boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Arylphosphanyl group, C ₆ ~ C ₆₀ Monoarylphosphinyl group, C ₆ ~ C ₆₀ Diarylphosphinyl group and C ₆ ~C ₆₀ selected from the group consisting of an arylamine group, or adjacent R ₁ (eg, R ₁ and other adjacent R ₁ ) may be bonded to each other to form a condensed ring;

In the Ar ₁ to Ar ₃ and R ₁ , an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl Boron group, aryl boron group, aryl phosphanyl group, monoaryl phosphinyl group, diaryl phosphinyl group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Monoaryl phosphinyl group, diaryl phosphinyl group and C ₆ ~ C ₆₀ It is unsubstituted or substituted with one or more substituents selected from the group consisting of an arylsilyl group, in which case, when the substituents are plural, the plural substituents are the same or different from each other).

In addition, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode, wherein at least one of the at least one organic material layer is represented by Formula 1 organic compounds.

Since the compound of the present invention has excellent thermal stability, carrier transport ability, light emitting ability, and the like, it can be usefully applied as an organic material layer material of an organic electroluminescent device.

In addition, the organic electroluminescent device including the compound of the present invention in the organic material layer has greatly improved aspects such as light emitting performance, driving voltage, lifespan, and efficiency, and thus can be effectively applied to a full color display panel.

1 is a cross-sectional view showing the structure of an organic electroluminescent device according to an embodiment of the present invention.
2 is a cross-sectional view showing the structure of an organic electroluminescent device according to another embodiment of the present invention.

Hereinafter, the present invention will be described in detail.

<New organic compound>

The present invention is a compound represented by Formula 1, for example, having a basic structure formed by condensing an indole derivative and a benzene derivative on one side of a benzene moiety of a 9,9-difluoro-9H-fluorene derivative, It has a structure in which one electron-withdrawing group (EWG) is combined.

Specifically, in the compound represented by Formula 1, the basic structure has excellent electrochemical stability and excellent carrier transport ability. In particular, the electron and hole transport mobility is very good, and thus the balance of carriers in the light emitting layer is very good.

Since an electron-withdrawing group (EWG) is bonded to this basic structure, the compound of Formula 1 has particularly excellent electron mobility. In addition, when the compound of Formula 1 is used as a material for the organic material layer of the OLED, since the charge balance between the holes and electrons transferred into the organic material layer of the compound is excellent, exciton generation is excellent. In addition, the bandgap of the compound is as narrow as about 3.24 eV. Accordingly, the compound of Formula 1 is suitable as a light emitting layer material, particularly a red host material.

In addition, the compound of Formula ₁ has _triplet energy ( Since the T1) difference is small, about 0.04 to 0.06 eV, energy transfer to the dopant is high, so that the luminous efficiency of the device may be improved, and durability and stability of the device may be improved, thereby effectively increasing the lifetime of the device. Here, the triplet energy (T1) of a general dopant [eg, (piq) ₂ Ir(acac), etc.] used in phosphorescent red is about 2.0 eV, and the compound of Formula 1 according to the present invention has triplet energy (T1) ) is about 2.04 to 2.06 eV, which is suitable for a red phosphorescent host.

For example, the dimethyl indenocarbazole compound (eg, Compound A) illustrated in Table 1 below has a triplet energy (T1) of about 2.5 to 2.6 eV, and a triplet energy (T1) difference with the dopant of about 0.5 Since it is as high as ~0.6 eV, energy transfer to the dopant is not easy, and the luminous efficiency of the device is low. In contrast, the compound represented by Formula 1 of the present invention (eg, compound R6) has a triplet energy (T1) of 2.06 eV, and the triplet energy difference with the dopant is small, so energy transfer to the dopant is easy .

compound Band Gap triplet energy (T1)

3.24 eV 2.06 eV

3.24 eV 2.59 eV

In addition, the dimethyl indenocarbazole compounds (eg, compound A) illustrated in Table 1 are susceptible to thermal decomposition because the dimethyl group moiety is weak to heat, and therefore thermal stability is low. On the other hand, the compound of the present invention has a high glass transition temperature, and thus excellent thermal stability, because the carbon (C)-fluorine (F) bond in the basic structure has a relatively strong bonding force compared to the carbon-carbon bond.

In addition, the compound of Formula 1 has a lower driving voltage and excellent lifespan characteristics compared to the dimethyl indenocarbazole compound.

Due to the foregoing, since the compound of Formula 1 according to the present invention has excellent light emitting properties, any one material of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, which are organic layers of an organic electroluminescent device It can be used as a material, preferably as a material of the green phosphorescence and red phosphorescence light emitting layer.

Accordingly, the compound represented by Formula 1 of the present invention is an organic layer material of an organic electroluminescent device, preferably a light emitting layer material (a red phosphorescent host material), an electron transport layer/injection layer material, a light emitting auxiliary layer material, an electron transport auxiliary layer It can be used as a material, more preferably a light emitting layer material, an electron transport layer material, or an electron transport auxiliary layer material. In addition, the performance and lifespan characteristics of the organic electroluminescent device including the compound of Formula 1 can be greatly improved, and the performance of a full color organic light emitting panel to which such an organic electroluminescent device is applied can also be maximized.

In the compound represented by Formula 1 according to the present invention, X is selected from the group consisting of O, S, N(Ar ₁ ) and C(Ar ₂ )(Ar ₃ ).

Here, Ar ₁ To Ar ₃ Are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro 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 of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 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 Alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphanyl group, C ₆ ~ C ₆₀ monoaryl phosphinyl group, C ₆ ~ C ₆₀ diaryl phosphinyl group and C ₆ ~ C ₆₀ arylamine group It may be selected from the group consisting of, or adjacent substituents may be bonded to each other to form a condensed ring.

Specifically, Ar ₁ To Ar ₃ Are the same as or different from each other, and each independently consists of a C ₆ ~ C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C ₆ ~ C ₆₀ arylamine group. may be selected from the group, and more specifically, Ar ₁ To Ar ₃ Are the same as or different from each other, and each independently a C ₆ ~ C ₃₀ aryl group, a heteroaryl group having 5 to 30 nuclear atoms, and C ₆ ~ It may be selected from the group consisting of a C ₃₀ arylamine group.

In addition, Y ₁ to Y ₁₂ are the same as or different from each other, and each independently represents C(R ₁ ) or N.

Here, when C(R ₁ ) is a plurality, a plurality of R ₁ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro 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, nuclear atoms 5 to 60 heteroaryl group, 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 Alkyl boron group of, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Monoaryl phosphinyl group, C ₆ ~ C ₆₀ Diaryl phosphinyl group and C ₆ ~ C ₆₀ may be selected from the group consisting of an arylamine group, or adjacent R ₁ may be bonded to each other to form a condensed ring.

Specifically, a plurality of R ₁ may be each independently selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms, or Adjacent R ₁ may be bonded to each other to form a condensed ring, and more specifically, a plurality of R ₁ are each independently hydrogen, a C ₁ to C ₂₀ alkyl group, a C ₆ to C ₃₀ aryl group, and the number of nuclear atoms. It may be selected from the group consisting of 5 to 30 heteroaryl groups, or adjacent R ₁ may be bonded to each other to form a condensed ring.

The bonding between the adjacent R ₁ is that any one of R ₁ among a plurality of R ₁ is coupled with another adjacent R ₁ , for example, ① Y ₁ =C(R ₁ ), Y ₂ = among Y ₁ to Y ₄ . when C(R ₁ ), a bond between R ₁ of Y ₁ and R 1 of R ₁ -Y ₂ ; When Y ₂ =C(R ₁ ), Y ₃ =C(R ₁ ), a bond between R ₁ of R ₁ -Y ₃ of Y ₂ and R 1 of Y 2 ; When Y ₃ =C(R ₁ ), Y ₄ =C(R ₁ ), a bond between R ₁ of R ₁ -Y ₄ of Y ₃ and R 1 of Y 4 ; ② Among Y ₅ ~ Y ₈ , when Y ₅ =C(R ₁ ), Y ₆ =C(R ₁ ), a bond between R ₁ of R ₁ -Y ₆ of Y ₅ ; When Y ₆ =C(R ₁ ), Y ₇ =C(R ₁ ), a bond between R ₁ of Y ₆ -R ₁ of Y ₇ ; When Y ₇ =C(R ₁ ), Y ₈ =C(R ₁ ), a bond between R ₁ of Y ₇ and R ₁ of Y ₈ ; ③ In Y ₉ ~Y ₁₂ , when Y ₉ =C(R ₁ ), Y ₁₀ =C(R ₁ ), a bond between R ₁ of Y ₉ and R ₁ of Y ₁₀ ; When Y ₁₀ =C(R ₁ ), Y ₁₁ =C(R ₁ ), a bond between R ₁ of Y ₁₀ and R ₁ of Y ₁₁ ; When Y ₁₁ =C(R ₁ ), Y ₁₂ =C(R ₁ ), there is a bond between R ₁ of Y ₁₁ and R ₁ of Y ₁₂₂ . In this case, a plurality of R ₁ are the same as or different from each other. These are combined to form a condensed ring, wherein the condensed ring is a monocyclic or polycyclic alicyclic ring, a monocyclic or polycyclic heteroalicyclic ring, a monocyclic or polycyclic aromatic ring, or a monocyclic or polycyclic heteroaromatic ring, , In this case, when there are a plurality of condensed rings, the plurality of condensed rings are the same as or different from each other. Specifically, the condensed ring may be a C ₆ ~ C ₁₈ aromatic ring, or a heteroaromatic ring having 5 to 18 nuclear atoms.

In the Ar ₁ to Ar ₃ and R ₁ , an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl Boron group, aryl boron group, aryl phosphanyl group, monoaryl phosphinyl group, diaryl phosphinyl group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Monoaryl phosphinyl group, diaryl phosphinyl group and C ₆ ~ C ₆₀ It is unsubstituted or substituted with one or more substituents selected from the group consisting of an arylsilyl group. In this case, when the substituents are plural, the plurality of substituents are the same or different from each other.

According to an example of the present invention, the compound represented by Formula 1 may be embodied as any one of the compound represented by Formula 2 to the compound represented by Formula 10 below.

In Formulas 2 to 10,

X and R ₁ are each as defined in Formula 1 above.

In addition, ring A may be a conventional hydrocarbon-based ring or a hydrocarbon-based ring containing one or more heteroatoms known in the art, and condensed, fused, bridged, or spirocyclic with other adjacent rings (eg, core structure). ) may be in a combined form. In this case, when there is a plurality of A rings, the plurality of A rings are the same as or different from each other.

For example, the A ring is a monocyclic or polycyclic alicyclic ring, a monocyclic or polycyclic heteroalicyclic ring, a monocyclic or polycyclic aromatic ring, or a monocyclic or polycyclic heteroaromatic ring, wherein the A ring is plural When , a plurality of A rings are the same or different from each other. Specifically, the A ring is preferably a C ₆ ~ C ₁₈ aromatic ring, or a heteroaromatic ring having 5 to 18 nuclear atoms.

a is an integer from 0 to 4, b is an integer from 0 to 3, and c is an integer from 0 to 2. wherein when a, b, and c are 0, each R ₁ is hydrogen. In addition, when a is an integer of 1 to 3, b is an integer of 1 to 3, when c is 1 or 2, each R ₁ is the aforementioned substituent except hydrogen, wherein each substituent is the same as or different from each other .

According to another example of the present invention, the compound represented by Formula 1 may be further embodied as any one of the compound represented by Formula 11 to the compound represented by Formula 22 below.

In Formulas 11 to 22,

R ₁ , Ar ₁ To Ar ₃ are each as defined in Formula 1.

According to one example, in Formula 1, at least one of a plurality of R ₁ and Ar ₁ may be a substituent having an electron withdrawing group (EWG) characteristic.

According to another example, at least one of a plurality of R ₁ and Ar ₁ may be a substituent represented by the following Chemical Formula 23. In this case, the substituent represented by the following formula (23) is preferably a substituent having an electron withdrawing group (EWG) characteristic. For example, in Formula 1, when X is N(Ar ₁ ), at least one of a plurality of R ₁ and Ar ₁ is preferably a substituent represented by Formula 23 below. In addition, in Formula 1, when X is O, S, or C(Ar ₂ )(Ar ₃ ), at least one of a plurality of R ₁ is preferably a substituent represented by Formula 23 below.

In Formula 23,

* denotes a site at which a bond with Chemical Formula 1 is formed.

In addition, L ₁ to L ₃ are a linker of a conventional divalent group known in the art, the same as or different from each other, and each independently a direct bond (or a single bond), or C ₆ ~ It is selected from the group consisting of a C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms.

Specific examples of L ₁ to L ₃ include a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, a pyrantrenylene group, a carbazolylene group, a thiophenylene group, an indolylene group, and a purinylene group. , a quinolinylene group, a pyrrolylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group, a pyrimidinylene group, and the like, but is not limited thereto.

In one example, L ₁ to L ₃ may be the same as or different from each other, and each independently may be a direct bond, or may be selected from linkers represented by the following Chemical Formulas S-A1 to S-A7.

In addition, in Formula 23, R ₂ is hydrogen, deuterium, halogen, cyano group, nitro 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 Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Arylphosphanyl group, C ₆ ~ C ₆₀ Monoaryl phosphinyl group, C ₆ ~ C ₆₀ Diaryl phosphinyl group and C ₆ ~ C ₆₀ It is selected from the group consisting of an arylamine group.

Specifically, R ₂ may be selected from the group consisting of a C ₆ ~ C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and an arylamine group of C ₆ ~ C ₆₀ More specifically, the following formula It may be selected from the substituents represented by S-B1 to S-B12.

In the above formulas S-B1 to S-B12,

* means a site connected to Formula 1 with or without a linker (eg, L ₁ to L ₃ ).

In addition, R ₃ and R ₄ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro 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 of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 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 Alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphanyl group, C ₆ ~ C ₆₀ monoaryl phosphinyl group, C ₆ ~ C ₆₀ diaryl phosphinyl group and C ₆ ~ C ₆₀ arylamine group It is selected from the group consisting of, and specifically, each independently hydrogen, a C ₁ to C ₄₀ alkyl group, C ₆ to C ₄₀ aryl group, and a heteroaryl group having 5 to 40 nuclear atoms may be selected from the group consisting of.

In this case, a plurality of R ₃ are the same as or different from each other, and a plurality of R ₄ are the same or different from each other.

In addition, n is an integer of 0 to 4, m is an integer of 0 to 3, l is an integer of 0 to 2, o and q are each an integer of 0 to 2, p and r are each an integer of 0 to 4 It is an integer, provided that o+p is 0≤o+p≤5, and q+r is 0≤q+r≤7. Here, when n, m, l, o, p, q, and r are each independently 0, R ₃ and R ₄ are each independently hydrogen, and n, p and r are each independently an integer of 1 to 4 , or when m is an integer of 1 to 3, and when l, o, and q are each independently 1 or 2, R ₃ and R ₄ may each independently be selected from the above-described substituents other than hydrogen, wherein each The substituents of are the same or different.

In addition, in Formula 23, the arylene group and heteroarylene group of L ₁ to L ₃ , and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, and alkylox group of R ₂ A group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, an arylboron group, an arylphosphanyl group, a monoarylphosphinyl group, a diarylphosphinyl group, and an arylamine group are each independently deuterium, halogen, cya No group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms , C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Arylamine group, C ₃ ~ C ₄₀ Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms , C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Arylphosphanyl group, C ₆ ~ C ₆₀ Monoaryl A phosphinyl group, a C ₆ ~ C ₆₀ diarylphosphinyl group and a C ₆ ~ C ₆₀ arylsilyl group is unsubstituted or substituted with one or more substituents selected from the group consisting of, in this case, when the substituents are plural, a plurality of The substituents are the same as or different from each other.

According to another example of the present invention, the compound represented by Formula 1 may be further specified as any one of the compounds represented by Formula 24 to Formula 36 below.

In the formulas 24-36,

Ar ₂ is as defined in Formula 1, L ₁ to L ₃ , and R ₂ are each as defined in Formula 23.

Specific examples of the compound represented by Formula 1 according to the present invention include, but are not limited to, the following compounds R1 to R160.

In the present invention, "alkyl" refers to a monovalent substituent derived from a linear 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, and the like.

In the present invention, "alkenyl" refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

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

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, adamantine, and the like.

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

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

In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. In this case, at least one carbon, preferably 1 to 3 carbons in the ring 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 or condensed may be included, and further, a form condensed with an aryl group may be included. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl), purinyl, quinolyl, benzothiazole, and carbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but is not limited thereto.

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

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, diphenyloxy, and the like.

In the present invention, "alkylsilyl" means a silyl substituted with an alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-, tri-alkylsilyl. In addition, "arylsilyl" means a silyl substituted with an 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, "alkyl boron group" means a boron group substituted with an alkyl having 1 to 40 carbon atoms, and "aryl boron group" means a boron group substituted with an aryl group 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" refers to a phosphine group substituted with 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 40 carbon atoms, and includes mono- as well as di-arylamines.

In the present invention, "condensed ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

<Organic electroluminescent device>

On the other hand, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by Formula 1 according to the present invention.

Specifically, the organic electroluminescent device according to the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is and a compound represented by Formula 1 above. In this case, the compound may be used alone or in combination of two or more.

The at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light emitting layer, a light emission auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, of which at least one organic material layer is the The compound represented by Formula 1 may be included. Preferably, the organic material layer containing the compound of Formula 1 may be at least one selected from the group consisting of 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, more preferably the Formula 1 The organic layer including the compound of may be at least one selected from the group consisting of a light emitting layer, an electron transport auxiliary layer, and an electron transport layer.

In one example, the at least one organic material layer 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 the compound represented by Formula 1 above. In this case, the compound represented by Formula 1 is a host material.

According to another example, the at least one organic material layer includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and the electron transport layer includes the compound represented by Formula 1 above. In this case, the compound represented by Formula 1 is a material for forming the electron transport layer.

According to another example, the at least one organic material layer 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 is a compound represented by Formula 1 include In this case, the compound represented by Formula 1 is a material for forming the electron transport auxiliary layer.

The structure of the organic electroluminescent device according to the present invention described above is not particularly limited, and may have a conventional structure known in the art. For example, the structure of the organic electroluminescent device may have a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode are sequentially stacked on a substrate.

1 is a cross-sectional view of an organic electroluminescent device according to an example of the present invention, wherein the organic electroluminescent device is positioned between the anode 10 and the cathode 20 facing each other, and the anode 10 and the cathode 20 and an organic material layer 30 that Here, the organic material layer 30 includes a hole transport layer 31 , a light emitting layer 32 and an electron transport layer 34 , and, if necessary, a hole transport auxiliary layer positioned between the hole transport layer 31 and the light emitting layer 32 . (33); and/or may further include an electron transport auxiliary layer 35 positioned between the electron transport layer 34 and the light emitting layer 32 . In the organic light emitting device, holes travel to the light emitting layer 32 at an ionization potential level at the anode. At this time, when the organic electroluminescent device further includes an electron transport auxiliary layer 35, holes moving to the light emitting layer 32 are blocked by the high energy barrier of the electron transport auxiliary layer and diffuse to the electron transport layer 34, Alternatively, it cannot move, and as a result, the electron transport auxiliary layer 35 functions to limit the holes to the light emitting layer. The function of limiting the holes to the light emitting layer 32 as described above prevents the diffusion of holes to the electron transport layer 34 that moves electrons by reduction, thereby suppressing the decrease in lifespan through an irreversible decomposition reaction due to oxidation. It may contribute to improving the lifespan of the organic light emitting diode. Meanwhile, electrons move from the cathode to the light emitting layer 32 . At this time, when the organic electroluminescent device further includes the hole transport auxiliary layer 33 , electrons moving to the light emitting layer 32 are blocked by the high energy barrier of the hole transport auxiliary layer and diffuse or move to the hole transport layer 31 . As a result, the hole transport auxiliary layer 33 may restrict electrons to the light emitting layer, thus contributing to improvement of the lifespan of the organic light emitting device.

According to another example, the organic electroluminescent device includes an anode 10; a negative electrode 20 opposite to the positive electrode; and an organic material layer 30 positioned between the anode 10 and the cathode 20 . In this case, the organic material layer 30 includes a hole transport layer 31 , a light emitting layer 32 and an electron transport layer 34 , and, if necessary, a hole transport auxiliary layer positioned between the hole transport layer 31 and the light emitting layer 32 . (33); an electron transport auxiliary layer 35 positioned between the light emitting layer 32 and the electron transport layer 34; a hole injection layer 37 positioned between the anode 10 and the hole transport layer 31; and at least one selected from the group consisting of an electron injection layer 36 positioned between the cathode 20 and the electron transport layer 34 (see FIG. 2 ).

In the present invention, the hole injection layer 37 is applied on top of ITO whose surface is not flat as well as improving the interface characteristics between ITO used as the anode and the organic material used as the hole transport layer 31, so that ITO It is a layer that has the function of making the surface smooth. The material for the hole injection layer 37 may be used without any particular limitation as long as it is commonly used in the art, for example, there is an amine-based compound, but is not limited thereto.

In addition, the electron injection layer 36 is laminated on the electron transport layer to facilitate electron injection from the cathode and ultimately improve power efficiency. The material for the electron injection layer 36 may be used without any particular limitation as long as it is commonly used in the art. Examples include, but are not limited to, LiF, Liq, NaCl, CsF, Li ₂ O, BaO, and the like.

Meanwhile, the organic electroluminescent device according to the present invention may optionally further include a light emitting auxiliary layer (not shown) between the hole transport auxiliary layer 33 and the light emitting layer 32 . The light emitting auxiliary layer may serve to transport holes to the light emitting layer 32 and to adjust the thickness of the organic material layer 30 . The light emitting auxiliary layer may include a hole transport material in the art, and may be made of the same material as the hole transport layer 31 .

In the present invention, the compound represented by Formula 1 has a structure in which an electron withdrawing group (EWG) is bonded to a 5-membered aromatic ring or a 5-membered aromatic heterocyclic group such as indole, indazole indene, benzofuran, benzothiophene, triazolo, etc. have Since this structure has an energy level similar to that of carbazole, it can be adjusted higher than the energy level of the dopant, and thus can be applied as a host material. In particular, since the moieties of benzofuran and benzothiophene are rich in electrons, mobility is increased when used as an electron transport layer material of an organic electroluminescent device, so that an increase in luminous efficiency and a decrease in driving voltage can be expected. In addition, since the 5-membered aromatic ring or 5-membered aromatic heterocyclic ring of the present invention has a smaller molecular weight than the existing compounds, deposition is possible at a relatively lower temperature than other materials, which has excellent processability and heat Stability can be improved.

Accordingly, the compound represented by Formula 1 of the present invention may be used as an organic material layer material of an organic electroluminescent device, specifically, any one of 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. It may be used as a material of any one of the light emitting layer, the electron transport layer, and the electron transport auxiliary layer positioned between the light emitting layer and the electron transport layer, more preferably, the electron transport layer or the electron transport auxiliary layer.

The light emitting layer of the organic electroluminescent device according to the present invention includes a host material, wherein the compound of Formula 1 may be included as a host material, or a conventional compound other than the compound of Formula 1 may be included as a host. . For example, when the compound represented by Formula 1 is used as a material for the light emitting layer, it may be used as a phosphorescent host, a fluorescent host, or a dopant material of the light emitting layer, preferably a phosphorescent host (a phosphorescent host of blue, green and/or red) material) can be used.

In addition, in the present invention, the organic electroluminescent device has a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked as described above, as well as an insulating layer or an adhesive layer at the interface between the electrode and the organic material layer. can have

The organic electroluminescent device of the present invention uses materials and methods known in the art, except that at least one of the organic material layers (eg, electron transport auxiliary layer) is formed to include the compound represented by Formula 1 above. It can be manufactured by forming another organic material layer and an electrode using it.

The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution application method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer method.

The substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films and sheets may be used.

In addition, the anode material may be made of, for example, a conductor having a high work function to facilitate hole injection, and may include 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, but is not limited thereto.

In addition, the negative electrode material may be made of, for example, a conductor having a low work function to facilitate electron injection, and may be formed of magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead. the same metal or alloys thereof; and a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

Hereinafter, the present invention will be described in detail through examples. However, the following examples only illustrate the present invention, and the present invention is not limited by the following examples.

[Preparation Example 1] Synthesis of compound A2

<Step 1> Synthesis of compound A1

1-bromo-2-nitrobenzene 3.4g (16.9 mmol), (7,7-difluoro-7H-benzo[c]fluoren-5-yl)boronic acid 6.0g (20.2 mmol), Pd(PPh ₃ ) under a nitrogen stream ₄ 1.0g (5 mol%), potassium carbonate 7.0g (50.6 mmol) and Toluene/H ₂ O/Ethanol (80ml/40ml/40ml) were added, and the mixture was stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound A1 (4.5 g, 12.1 mmol, yield: 72%).

GC-Mass (theoretical: 373.36 g/mol, measured: 373 g/mol)

1H-NMR: δ 7.39 to 7.61 (m, 7H), 7.65 (s, 1H), 7.78 to 7.89 (m, 5H)

<Step 2> Synthesis of compound A2

Compound A1 4.5g (12.1 mmol), triphenylphosphine (PPh ₃ ) 8.0g (30.4 mmol), and 1,2-dichlorobenzene (DCB) (50 ml) were added under a nitrogen stream, followed by stirring for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound A2 (3.1 g, 9.0 mmol, yield: 74%).

GC-Mass (theoretical: 341.36 g/mol, measured: 341 g/mol)

1H-NMR: δ 7.39 to 7.60 (m, 7H), 7.78 to 7.89 (m, 5H), 10.02 (s, 1H)

[Preparation Example 2] Synthesis of compound B2

<Step 1> Synthesis of compound B1

3-bromo-4-nitropyridine 3.4 g (16.9 mmol), (7,7-difluoro-7H-benzo [c] fluoren-5-yl) boronic acid 6.0 g (20.2 mmol), Pd (PPh ₃ ) under a nitrogen stream ₄ 1.0g (5 mol%), potassium carbonate 7.0g (50.6 mmol) and Toluene/H ₂ O/Ethanol (80ml/40ml/40ml) were added, and the mixture was stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound B1 (4.6 g, 12.1 mmol, yield: 72%).

GC-Mass (theoretical: 374.35 g/mol, measured: 374 g/mol)

1H-NMR: δ 7.39 to 7.58 (m, 5H), 7.65 (s, 1H), 7.78 to 7.89 (m, 5H), 9.05 (s, 1H)

<Step 2> Synthesis of compound B2

Compound B1 4.6g (12.1 mmol), triphenylphosphine 8.0g (30.4 mmol), and 1,2-dichlorobenzene (50 ml) were added under a nitrogen stream, followed by stirring for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound B2 (3.1 g, 9.0 mmol, yield: 74%).

GC-Mass (theoretical: 342.35 g/mol, measured: 342 g/mol)

1H-NMR: δ 7.41 to 7.58 (m, 5H), 7.78 to 7.89 (m, 5H), 9.05 (s, 1H), 10.00 (s, 1H)

[Preparation Example 3] Synthesis of compound C2

<Step 1> Synthesis of compound C1

1-bromo-2-nitronaphthalene 4.3 g (16.9 mmol), (7,7-difluoro-7H-benzo [c] fluoren-5-yl) boronic acid 6.0 g (20.2 mmol), Pd (PPh ₃ ) under a nitrogen stream ₄ 1.0g (5 mol%), potassium carbonate 7.0g (50.6 mmol) and Toluene/H ₂ O/Ethanol (80ml/40ml/40ml) were added, and the mixture was stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound C1 (5.0 g, 11.8 mmol, yield: 70%).

GC-Mass (theoretical: 423.42 g/mol, measured: 423 g/mol)

1H-NMR: δ 7.39 to 7.62 (m, 8H), 7.65 (s, 1H), 7.79 to 7.89 (m, 6H)

<Step 2> Synthesis of compound C2

5.0 g (11.8 mmol) of Compound C1, 7.7 g (29.5 mmol) of triphenylphosphine, and 1,2-dichlorobenzene (50 ml) were added under a nitrogen stream, followed by stirring for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, C2 (3.3g, 8.4 mmol, yield: 71%).

GC-Mass (theoretical: 391.42 g/mol, measured: 391 g/mol)

1H-NMR: δ 7.40 to 7.62 (m, 8H), 7.79 to 7.89 (m, 6H), 10.01 (s, 1H)

[Preparation Example 4] Synthesis of compound D2

<Step 1> Synthesis of compound D1

1-bromo-2-nitrobenzene 3.4g (16.9 mmol), (7,7-difluoro-7H-dibenzo[c,g]fluoren-5-yl)boronic acid 7.0g (20.2 mmol), Pd(PPh) under a nitrogen stream ₃ ) ₄ 1.0g (5 mol%), potassium carbonate 7.0g (50.6 mmol) and Toluene/H ₂ O/Ethanol (80ml/40ml/40ml) were added, and the mixture was stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound D1 (5.0 g, 11.8 mmol, yield: 70%).

GC-Mass (theoretical: 423.42 g/mol, measured: 423 g/mol)

1H-NMR: δ 7.40 to 7.60 (m, 8H), 7.64 (s, 1H), 7.79 to 7.89 (m, 6H)

<Step 2> Synthesis of compound D2

5.0 g (11.8 mmol) of compound D1, 7.7 g (29.5 mmol) of triphenylphosphine, and 1,2-dichlorobenzene (50 ml) were added under a nitrogen stream, followed by stirring for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound D2 (3.3 g, 8.4 mmol, yield: 71%).

GC-Mass (theoretical: 391.42 g/mol, measured: 391 g/mol)

1H-NMR: δ 7.41 to 7.62 (m, 8H), 7.79 to 7.88 (m, 6H), 10.01 (s, 1H)

[Preparation Example 5] Synthesis of compound E1

2-bromo-14,14-difluoro-13-phenyl-13,14-dihydrobenzo[c]indeno[2,1-a]carbazole 12.1g (24.4 mmol), 4,4,4',4' under nitrogen stream ,5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 7.4 g ( 29.2 mmol), Pd(dppf)Cl ₂ 0.6 g ( 0.7 mmol), KOAc 7.2 g (73.1 mmol) and 1,4-Dioxane (200 ml) were mixed and stirred at 130° C. for 6 hours.

After completion of the reaction, the organic layer was extracted with ethyl acetate, water was removed with MgSO ₄ , and purified by column chromatography to obtain the target compound E1 (9.3 g, 17.1 mmol, yield: 70%).

GC-Mass (theoretical: 543.42 g/mol, measured: 543 g/mol)

1H-NMR: δ 1.25 (s, 12H), 7.15 to 7.45 (m, 9H), 7.55 (s, 1H), 7.81 to 8.00 (m, 6H)

[Preparation Example 6] Synthesis of compound F1

2-bromo-14,14-difluoro-13,13-dimethyl-13,14-dihydrobenzo[c]indeno[2,1-a]fluorine 10.9g (24.4 mmol), 4,4,4' under a nitrogen stream 4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 7.4 g ( 29.2 mmol), Pd(dppf)Cl ₂ 0.6 g ( 0.7 mmol), 7.2 g (73.1 mmol) of KOAc and 1,4-Dioxane (200 ml) were mixed and stirred at 130° C. for 6 hours.

After completion of the reaction, the organic layer was extracted with ethyl acetate, water was removed with MgSO ₄ , and purified by column chromatography to obtain the target compound F1 (8.4 g, 17.1 mmol, yield: 70%).

GC-Mass (Theory: 494.39 g/mol, Measured: 499 g/mol)

1H-NMR: δ 1.25 (s, 12H), 1.72 (s, 6H), 7.18 to 7.45 (m, 4H), 7.55 (s, 1H), 7.81 to 8.08 (m, 6H)

[Preparation Example 7] Synthesis of compound G1

2-bromo-14,14-difluoro-14H-benzo[3,4]fluoreno[1,2-b]benzofuran 10.3g (24.4 mmol), 4,4,4',4',5,5 under nitrogen stream ,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 7.4 g ( 29.2 mmol), Pd(dppf)Cl ₂ 0.6 g ( 0.7 mmol), KOAc 7.2 g ( 73.1 mmol) ) and 1,4-Dioxane (200 ml) were mixed and stirred at 130° C. for 6 hours.

After completion of the reaction, the organic layer was extracted with ethyl acetate, water was removed with MgSO ₄ , and purified by column chromatography to obtain the target compound G1, (8.6 g, 18.3 mmol, yield 75%).

GC-Mass (Theory: 468.31 g/mol, Measured: 468 g/mol)

1H-NMR: δ 1.25 (s, 12H), 7.18 to 7.44 (m, 4H), 7.59 (s, 1H), 7.80 to 8.08 (m, 6H)

[Synthesis Example 1] Synthesis of compound R1

Compound A2 3.1 g (9.0 mmol), 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine 4.6 g ( 9.9mmol), Pd ₂ (dba) ₃ 0.4g (5 mol%), tri- tert -butylphosphine 0.1g (0.4mmol), Sodium tert-butoxide 2.6g (27.0mmol) and Toluene (100ml) were added, and 110℃ was stirred for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . Purification by column chromatography gave 4.2 g (5.8 mmol, yield: 65%) of the target compound, R1.

GC-Mass (theoretical: 724.8 g/mol, measured: 725 g/mol)

[Synthesis Example 2] Synthesis of compound R5

Compound A2 3.1g (9.0mmol), 2-bromo-4,6-diphenyl-1,3,5-triazine 3.1g (9.9mmol), Pd ₂ (dba) ₃ 0.4g (5 mol%) under a nitrogen stream, Tri- tert -butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide 2.6 g (27.0 mmol) and toluene (100 ml) were added, and the mixture was stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . Purification by column chromatography gave 3.3 g (5.8 mmol, yield: 65%) of the target compound, R5.

GC-Mass (theoretical: 572.6 g/mol, measured: 573 g/mol)

[Synthesis Example 3] Synthesis of compound R6

Compound A2 3.1 g (9.0 mmol), 2-bromo-4-phenylquinazoline 2.8 g (9.9 mmol), Pd ₂ (dba) ₃ 0.4 g (5 mol %), tri- tert -butylphosphine 0.1 g (0.4 mmol) under a nitrogen stream ), sodium tert-butoxide 2.6g (27.0mmol) and Toluene (100ml) were added, and the mixture was stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . Purification by column chromatography gave 3.2 g (5.8 mmol, yield: 65%) of the target compound, R6.

GC-Mass (theoretical: 545.6 g/mol, measured: 546 g/mol)

[Synthesis Example 4] Synthesis of compound R7

Compound A2 3.1g (9.0mmol), 2-bromo-4-phenylbenzo[h]quinazoline 3.3g (9.9mmol), Pd ₂ (dba) ₃ 0.4g (5 mol%) of tri- tert -butylphosphine under a nitrogen stream 0.1 g (0.4 mmol) Sodium tert-butoxide 2.6 g (27.0 mmol) and Toluene (100 ml) were added, and the mixture was stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . Purification by column chromatography gave 3.4 g (5.7 mmol, yield: 63%) of the target compound, R7.

GC-Mass (theoretical: 595.7 g/mol, measured: 596 g/mol)

[ Synthesis example 5] Synthesis of compound R8

Compound A2 3.1 g (9.0 mmol), 2-bromo-3-phenylquinoxaline 2.8 g (9.9 mmol), Pd ₂ (dba) ₃ 0.4 g (5 mol %), tri- tert -butylphosphine 0.1 g (0.4 mmol) under a nitrogen stream ), sodium tert-butoxide 2.6g (27.0mmol) and Toluene (100ml) were added, and the mixture was stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . Purification by column chromatography gave 3.1 g (5.7 mmol, yield: 63%) of the target compound, R8.

GC-Mass (theoretical: 545.6 g/mol, measured: 546 g/mol)

[Synthesis Example 6] Synthesis of compound R10

Compound A2 3.1g (9.0mmol), 2-bromo-4-phenylbenzofuro[3,2-d]pyrimidine 3.2g (9.9mmol), Pd ₂ (dba) ₃ 0.4g (5 mol%), tri- 0.1 g (0.4 mmol) of tert -butylphosphine, 2.6 g (27.0 mmol) of sodium tert-butoxide and Toluene (100 ml) were added, and the mixture was stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . Purification by column chromatography gave 3.3 g (5.7 mmol, yield: 63%) of the target compound, R10.

GC-Mass (theoretical: 585.6 g/mol, measured: 586 g/mol)

[Synthesis Example 7] Synthesis of compound R25

Compound B2 3.1g (9.0mmol), 2-bromo-4,6-diphenyl-1,3,5-triazine 3.1g (9.9mmol), Pd ₂ (dba) ₃ 0.4g (5 mol%) under a nitrogen stream, Tri- tert -butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide 2.6 g (27.0 mmol), and toluene (100 ml) were added, and the mixture was stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . Purification by column chromatography gave 3.4 g (5.8 mmol, yield: 65%) of the target compound, R25.

GC-Mass (theoretical: 573.6 g/mol, measured: 574 g/mol)

[Synthesis Example 8] Synthesis of compound R26

Compound B2 3.1 g (9.0 mmol), 2-bromo-4-phenylquinazoline 2.8 g (9.9 mmol), Pd ₂ (dba) ₃ 0.4 g (5 mol %), tri- tert -butylphosphine 0.1 g (0.4 mmol) under a nitrogen stream ), sodium tert-butoxide 2.6 g (27.0 mmol), and toluene (100 ml) were added, and the mixture was stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . Purification by column chromatography gave 3.2 g (5.8 mmol, yield: 65%) of the target compound, R26.

GC-Mass (theoretical: 546.6 g/mol, measured: 547 g/mol)

[Synthesis Example 9] Synthesis of compound R41

Compound C2 3.3g (8.4mmol), 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine 4.3g ( 9.2mmol), Pd ₂ (dba) ₃ 0.4g (5 mol%), tri- tert -butylphosphine 0.1g (0.4mmol), sodium tert-butoxide 2.4g (25.2mmol) and Toluene (100ml) were added, and then 110℃ was stirred for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . Purification by column chromatography gave the target compound, R41, 4.2g (5.4mmol, yield: 65%).

GC-Mass (theoretical: 774.9 g/mol, measured: 775 g/mol)

[Synthesis Example 10] Synthesis of compound R45

Compound C2 3.3g (8.4mmol), 2-bromo-4,6-diphenyl-1,3,5-triazine 2.9g (9.2mmol), Pd ₂ (dba) ₃ 0.4g (5 mol%) under a nitrogen stream; Tri- tert -butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide 2.4 g (25.2 mmol) and toluene (100 ml) were added, and the mixture was stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . Purification by column chromatography gave the target compound, R45, 3.4g (5.4mmol, yield: 65%).

GC-Mass (theoretical: 622.7 g/mol, measured: 623 g/mol)

[Synthesis Example 11] Synthesis of compound R61

Compound D2 3.3g (8.4mmol), 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine 4.3g ( 9.2mmol), Pd ₂ (dba) ₃ 0.4g (5 mol%), tri- tert -butylphosphine 0.1g (0.4mmol), sodium tert-butoxide 2.4g (25.2mmol) and Toluene (100ml) were added, and then 110℃ was stirred for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . Purification by column chromatography gave the target compound R61 4.1g (5.3mmol, yield: 63%).

GC-Mass (theoretical: 774.9 g/mol, measured: 775 g/mol)

[Synthesis Example 12] Synthesis of compound R65

Compound D2 3.3g (8.4mmol), 2-bromo-4,6-diphenyl-1,3,5-triazine 2.9g (9.2mmol), Pd ₂ (dba) ₃ 0.4g (5 mol%) under a nitrogen stream, Tri- tert -butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide 2.4 g (25.2 mmol) and toluene (100 ml) were added, and the mixture was stirred at 110° C. for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . Purification by column chromatography gave 3.3 g (5.3 mmol, yield: 63%) of the target compound, R65.

GC-Mass (theoretical: 622.7 g/mol, measured: 623 g/mol)

[Synthesis Example 13] Synthesis of compound R85

Compound E1 9.3g (17.1 mmol), 2-bromo-4,6-diphenyl-1,3,5-triazine 6.4g (20.5 mmol), Pd(PPh ₃ ) ₄ 1.0g (5 mol%) under a nitrogen stream, Potassium carbonate 7.1g (51.2 mmol) and Toluene/H ₂ O/Ethanol (80ml/40ml/40ml) were added, and the mixture was stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, R85 (8.0 g, 12.3 mmol, yield: 72%).

GC-Mass (theoretical: 648.7 g/mol, measured: 645 g/mol)

[Synthesis Example 14] Synthesis of compound R105

Compound F1 8.4 g (17.1 mmol), 2-bromo-4,6-diphenyl-1,3,5-triazine 6.4 g (20.5 mmol), Pd(PPh ₃ ) ₄ 1.0 g (5 mol%) under a nitrogen stream, Potassium carbonate 7.1g (51.2 mmol) and Toluene/H ₂ O/Ethanol (80ml/40ml/40ml) were added, and the mixture was stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound R105 (7.4g, 12.3 mmol, yield: 72%).

GC-Mass (theoretical: 599.7 g/mol, measured: 600 g/mol)

[Synthesis Example 15] Synthesis of compound R125

Compound G1 8.6 g (18.3 mmol), 2-bromo-4,6-diphenyl-1,3,5-triazine 6.8 g (21.9 mmol), Pd(PPh ₃ ) ₄ 1.0 g (5 mol%) under a nitrogen stream; Potassium carbonate 7.6g (54.8 mmol) and Toluene/H ₂ O/Ethanol (80ml/40ml/40ml) were added, and the mixture was stirred at 110° C. for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound R125 (7.5 g, 13.2 mmol, yield: 72%).

GC-Mass (theoretical: 573.6 g/mol, measured: 574 g/mol)

[Example 1] Fabrication of a red organic EL device

Compound R5 synthesized in Synthesis Example 2 was subjected to high-purity sublimation purification by a commonly known method, and then a red organic electroluminescent device was manufactured according to the following procedure.

First, a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After that, it is ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then the substrate is washed using UV for 5 minutes, The substrate was transferred to a vacuum evaporator.

On the thus prepared ITO transparent electrode, m-MTDATA (60 nm)/TCTA (80 nm)/90 wt% of compound R5 + 10 wt% (piq) ₂ Ir(acac) (300nm)/BCP (10 nm)/Alq ₃ (30 nm)/LiF (1 nm)/Al (200 nm) were stacked in the order to fabricate an organic electroluminescent device. The structures of m-MTDATA, (piq) ₂ Ir(acac), and BCP used at this time are as follows.

[Examples 2 to 12] Preparation of red organic EL device

A red organic EL device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 2 were used instead of the compound R5 used as the light emitting host material when the light emitting layer was formed in Example 1.

[Comparative Example 1]

A red organic EL device was manufactured in the same manner as in Example 1, except that the following CBP was used instead of the compound R5 used as a light emitting host material when the light emitting layer was formed in Example 1.

[ comparative example 2]

A red organic EL device was manufactured in the same manner as in Example 1, except that the following compound A was used instead of the compound R5 used as a light emitting host material when the light emitting layer was formed in Example 1.

[Evaluation Example 1]

For each of the organic electroluminescent devices manufactured in Examples 1 to 12 and Comparative Examples 1 to 2, the driving voltage and current efficiency at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 2 below.

Sample host Driving voltage (V) EL peak (nm) Current efficiency (cd/A) Example 1 R5 4.3 621 18.5 Example 2 R6 4.3 621 17.1 Example 3 R7 4.3 621 18.3 Example 4 R8 4.4 621 17.2 Example 5 R10 4.0 621 16.5 Example 6 R25 4.7 621 18.8 Example 7 R26 4.8 621 16.9 Example 8 R45 4.5 621 18.1 Example 9 R65 4.3 621 17.2 Example 10 R85 4.2 621 16.9 Example 11 R105 4.6 621 17.1 Example 12 R125 4.8 621 16.0 Comparative Example 1 CBP 6.1 622 9.0 Comparative Example 2 A 5.3 621 11.1

As shown in Table 2, the red organic electroluminescent devices (Examples 1 to 12) using the compounds (R5 to R125) according to the present invention as a host material for the light emitting layer are conventional red organic electroluminescent devices using CBP as a host material for the light emitting layer. It was found that the electroluminescent device (Comparative Example 1) and the red organic electroluminescent device (Comparative Example 2) using the compound A as a host material for the light emitting layer showed superior performance in terms of current efficiency and driving voltage.

[Example 13] Fabrication of green organic EL device

After high-purity sublimation purification of compound R1 synthesized in Synthesis Example 1 by a commonly known method, a blue organic EL device was manufactured according to the following procedure.

First, a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After that, it is ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then the substrate is washed using UV for 5 minutes, The substrate was transferred to a vacuum evaporator.

m-MTDATA (60 nm)/TCTA (80 nm)/90 wt% of compound R1 + 10 wt% Ir(ppy) ₃ (300 nm)/BCP (10 nm)/Alq ₃ (30 nm) on the prepared ITO transparent electrode )/LiF (1 nm)/Al (200 nm) were stacked in the order to fabricate a green organic EL device. The structures of m-MTDATA, TCTA, Ir(ppy) ₃ and BCP used at this time are as follows.

[Examples 14 to 22] Preparation of green organic EL device

A green organic EL device was manufactured in the same manner as in Example 13, except that the compounds shown in Table 3 were used instead of the compound R1 used as the light emitting host material when the light emitting layer was formed in Example 13.

[Comparative Example 3] Preparation of green organic EL device

A green organic EL device was manufactured in the same manner as in Example 13, except that the following CBP was used instead of the compound R1 used as a light emitting host material when the light emitting layer was formed in Example 13.

[Comparative Example 4] Preparation of green organic EL device

A green organic EL device was manufactured in the same manner as in Example 13, except that the following compound B was used instead of the compound R1 used as the light emitting host material when the light emitting layer was formed in Example 13.

[ evaluation example 2]

For each of the green organic EL devices fabricated in Examples 13 to 22 and Comparative Examples 3 to 4, the driving voltage, current efficiency, and emission peak at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 3 below. It was.

Sample host Driving voltage (V) EL peak (nm) Current efficiency (cd/A) Example 13 R1 4.2 515 19.8 Example 14 R5 4.3 515 20.8 Example 15 R25 4.9 515 23.2 Example 16 R41 4.9 515 24.2 Example 17 R45 4.2 515 21.2 Example 18 R61 4.2 515 21.2 Example 19 R65 4.3 515 21.5 Example 20 R85 4.3 515 21.4 Example 21 R105 4.3 515 20.8 Example 22 R125 4.2 515 20.9 Comparative Example 3 CBP 7.1 516 11.0 Comparative Example 4 B 5.5 515 17.3

As shown in Table 3, the green organic electroluminescent devices (Examples 13 to 22) using the compounds (R1 to R125) according to the present invention as a host material for the light emitting layer (Examples 13 to 22), the conventional organic electric field using CBP as a host material for the light emitting layer It was found that the light emitting device (Comparative Example 3) and the green organic electroluminescent device using the compound B as a host material for the light emitting layer (Comparative Example 4) showed superior performance in terms of current efficiency and driving voltage.

[ Example 23] blue organic electric field Fabrication of light emitting devices

After high-purity sublimation purification of compound R1 synthesized in Synthesis Example 1 by a commonly known method, a blue organic EL device was manufactured according to the following procedure.

First, a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was washed with distilled water ultrasonically. After that, it is ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then the substrate is cleaned using UV for 5 minutes and vacuum evaporator The substrate was transferred to

On the ITO transparent electrode prepared as above, DS-205 (Doosan Electronics Co., Ltd. 80 nm)/NPB (15 nm)/95% by weight of ADN + 5% by weight DS-405 (Doosan Electronics, 30nm)/Compound R1 (5 nm)/Alq ₃ (25 nm)/LiF (1 nm)/Al (200 nm) were stacked in the order to prepare an organic electroluminescent device. The structures of NPB, ADN and Alq ₃ used at this time are as follows.

[Examples 24 to 25] Fabrication of a blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 23, except that the compounds shown in Table 4 were used instead of the compound R1 as the electron transport auxiliary layer material in Example 23.

[Comparative Example 5] Preparation of blue organic electroluminescent device]

Except for using the compound R1 used as the electron transport auxiliary layer material in Example 23, and depositing at 30 nm instead of depositing Alq ₃ as the electron transport layer material at 25 nm, in the same manner as in Example 23, A blue organic electroluminescent device was fabricated.

[Evaluation Example 3]

For the blue organic electroluminescent devices prepared in Examples 23 to 25 and Comparative Example 5, respectively, the driving voltage, the emission wavelength, and the current efficiency at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 4 below. .

Sample Electron transport auxiliary layer (thickness) electron transport layer
(thickness) Driving voltage (V) Emission peak (nm) Current efficiency (cd/A) Example 23 R1 (5 nm) Alq ₃ (25 nm) 4.0 455 6.8 Example 24 R25 (5 nm) Alq ₃ (25 nm) 4.3 455 7.3 Example 25 R26 (5 nm) Alq ₃ (25 nm) 4.3 455 7.2 Comparative Example 5 - Alq ₃ (30 nm) 4.8 458 6.2

As shown in Table 4, the blue organic electroluminescent devices (Examples 23 to 25) using the compounds (R1 to R26) of the present invention as an electron transport auxiliary layer material are blue organic electroluminescent devices without an electron transport auxiliary layer ( Compared to Comparative Example 5), it was found that the performance was excellent in terms of current efficiency, emission peak and driving voltage.

[ Example 26] blue organic electric field Fabrication of light emitting devices

Compound R85 synthesized in Synthesis Example 13 was subjected to high-purity sublimation purification by a commonly known method, and then a blue organic EL device was manufactured according to the following procedure.

First, a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was washed with distilled water ultrasonically. After that, it is ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then the substrate is washed using UV for 5 minutes, and vacuum The substrate was transferred to an evaporator.

On the ITO transparent electrode prepared as above, DS-205 (Doosan Electronics, 80 nm)/NPB (15 nm)/95% by weight of ADN + 5% by weight DS-405 (Doosan Electronics, 30nm)/Compound R85 ( 30 nm)/LiF (1 nm)/Al (200 nm) were stacked in the order to fabricate a blue organic electroluminescent device.

[Examples 27-28] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 26, except that the compounds shown in Table 5 were used instead of the compound R85 used as the electron transport layer material in Example 26.

[Comparative Example 6] Fabrication of a blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 26, except that Alq ₃ was used instead of the compound R85 used as an electron transport layer material in Example 26.

[Comparative Example 7] Fabrication of a blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 26, except that the compound R85 used as an electron transport layer material in Example 26 was not used.

[Evaluation Example 4]

For the blue organic electroluminescent devices manufactured in Examples 26 to 28 and Comparative Examples 6 to 7, respectively, the driving voltage, current efficiency, and emission wavelength at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 5 below. indicated.

Sample electron transport layer Driving voltage (V) Emission peak (nm) Current efficiency (cd/A) Example 26 R85 4.1 455 6.2 Example 27 R105 4.1 455 6.9 Example 28 R125 3.8 455 6.0 Comparative Example 6 Alq ₃ 5.5 458 4.3 Comparative Example 7 - 6.5 460 3.8

As shown in Table 5, the blue organic electroluminescent devices (Examples 26 to 28) using the compounds (R85 to R125) of the present invention for the electron transport layer are blue organic electroluminescent devices using the conventional Alq ₃ as the electron transport layer material. (Comparative Example 6) and the blue organic EL device without an electron transport layer (Comparative Example 7) showed superior performance in terms of driving voltage, emission peak and current efficiency.

10: positive electrode, 20: negative electrode,
30: organic layer, 31: hole transport layer,
32: light emitting layer, 33: hole transport auxiliary layer,
34: electron transport layer, 35: electron transport auxiliary layer,
36: electron injection layer, 37: hole injection layer

Claims (9)

A compound represented by the formula (1):
[Formula 1]

In Formula 1,
X is selected from the group consisting of O, S, N(Ar ₁ ) and C(Ar ₂ )(Ar ₃ ),
Ar ₁ To Ar ₃ Are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ of Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Monoaryl phosphinyl group, C ₁₂ ~ C ₆₀ Diaryl phosphinyl group and C ₆ ~ C ₆₀ The group consisting of an arylamine group may be selected from, or adjacent substituents may combine with each other to form a condensed ring;
Y ₁ To Y ₁₂ Are the same as or different from each other, and each independently C(R ₁ ) or N,
When C(R ₁ ) is a plurality, a plurality of R ₁ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ of 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, heteroatom 5 to 60 Aryl group, 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 Alkyl Boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Arylphosphanyl group, C ₆ ~ C ₆₀ Monoaryl phosphinyl group, C ₁₂ ~ C ₆₀ Diaryl phosphinyl group and C ₆ ~ C ₆₀ may be selected from the group consisting of an arylamine group, or adjacent R ₁ may be bonded to each other to form a condensed ring;
In the Ar ₁ to Ar ₃ and R ₁ , an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl Boron group, aryl boron group, aryl phosphanyl group, monoaryl phosphinyl group, diaryl phosphinyl group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Monoaryl phosphinyl group, diaryl phosphinyl group and C ₆ ~ C ₆₀ It is unsubstituted or substituted with one or more substituents selected from the group consisting of an arylsilyl group, in which case, when the substituents are plural, the plural substituents are the same or different from each other). According to claim 1,
A compound represented by any one of the following Chemical Formulas 2 to 10:
[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

(In Formulas 2 to 10,
X and R ₁ are each as defined in claim 1,
Ring A is a monocyclic or polycyclic alicyclic ring, a monocyclic or polycyclic heteroalicyclic ring, a monocyclic or polycyclic aromatic ring, or a monocyclic or polycyclic heteroaromatic ring, wherein when there are plural A rings, plural A ring of is the same as or different from each other,
a is an integer from 0 to 4,
b is an integer from 0 to 3,
c is an integer from 0 to 2). According to claim 1,
A compound represented by any one of the following formulas 11 to 22:
[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

[Formula 22]

(In Formulas 11 to 22,
R ₁ , Ar ₁ To Ar ₃ are each as defined in claim 1). 4. The method of claim 3,
A compound characterized in that at least one of the plurality of R ₁ and Ar ₁ is a substituent represented by the following formula (23):
[Formula 23]

In Formula 23,
* is a site at which a bond with Formula 1 is formed;
L ₁ To L ₃ Are the same as or different from each other, and are each independently selected from the group consisting of a direct bond, a C ₆ ~ C ₁₈ arylene group, and a heteroarylene group having 5 to 18 nuclear atoms;
R ₂ is hydrogen, deuterium, halogen, cyano group, nitro 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, A heterocycloalkyl group having 3 to 40 nuclear atoms, 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 , C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha a nyl group, a C ₆ ~ C ₆₀ monoarylphosphinyl group, a C ₁₂ ~ C ₆₀ diarylphosphinyl group, and a C ₆ ~ C ₆₀ arylamine group;
The arylene group and heteroarylene group of L ₁ to L ₃ , the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, and alkyl of R ₂ A silyl group, an arylsilyl group, an alkylboron group, an arylboron group, an arylphosphanyl group, a monoarylphosphinyl group, a diarylphosphinyl group, and an arylamine group are each independently deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Arylphosphanyl group, C ₆ ~ C ₆₀ Monoaryl phosphinyl group, C ₁₂ ~ C ₆₀ Diarylphosphinyl group and C ₆ ~ C ₆₀ Arylsilyl group is substituted or unsubstituted with one or more substituents selected from the group consisting of, In this case, when the substituents are plural, the plurality of substituents are the same or different from each other ). 5. The method of claim 4,
Wherein L ₁ To L ₃ Are the same as or different from each other, and each independently a direct bond, or a compound selected from linkers represented by the following formulas S-A1 to S-A7:

5. The method of claim 4,
Wherein R ₂ is a compound characterized in that it is selected from substituents represented by the following formulas S-B1 to S-B12:

(In the formulas S-B1 to S-B12,
R ₃ and R ₄ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ of Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group, C ₆ ~ C ₆₀ Monoaryl phosphinyl group, C ₁₂ ~ C ₆₀ Diaryl phosphinyl group and C ₆ ~ C ₆₀ The group consisting of an arylamine group is selected from
In this case, a plurality of R ₃ are the same as or different from each other, and a plurality of R ₄ are the same or different from each other;
n is an integer from 0 to 4,
m is an integer from 0 to 3,
l is an integer from 0 to 2,
o and q are each an integer from 0 to 2,
p and r are each an integer from 0 to 4,
However, o+p is 0≤o+p≤5, and q+r is 0≤q+r≤7). 5. The method of claim 4,
A compound represented by any one of the following Chemical Formulas 24 to 36:
[Formula 24]

[Formula 25]

[Formula 26]

[Formula 27]

[Formula 28]

[Formula 29]

[Formula 30]

[Formula 31]

[Formula 32]

[Formula 33]

[Formula 34]

[Formula 35]

[Formula 36]

(In the formulas 24-36,
Ar ₁ is as defined in claim 1, L ₁ to L ₃ , and R ₂ are as defined in claim 4). An anode, a cathode, and one or more organic material layers interposed between the anode and the cathode,
At least one of the one or more organic material layers is an organic electroluminescent device comprising the compound according to any one of claims 1 to 7. 9. The method of claim 8,
The organic layer containing the compound is an organic electroluminescent device, characterized in that selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and an electron transport auxiliary layer.

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