KR20080047252A - An imidazopyridine-based compound and an organic light emitting diode employing an organic layer comprising the same - Google Patents

Abstract

An imidazopyridine-based compound is provided to show high electron transporting capability. An organic light emitting diode including an organic layer having the imidazopyridine-based compound is provided to show low driving voltages, high current densities, high luminance, high efficiencies and long life-times. An imidazopyridine-based compound is represented by a formula(1), wherein each R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11 and R12 is independently selected from the group consisting of H, halogen, hydroxyl, cyano, substituted and unsubstituted C1-30 alkyl, substituted and unsubstituted C1-30 alkoxy, substituted and unsubstituted C1-30 acyl, substituted and unsubstituted C2-30 alkenyl, substituted and unsubstituted C2-30 alkynyl, substituted and unsubstituted C6-30 aryl, and substituted and unsubstituted C3-30 heteroaryl; at least two of R4, R5, R6 and R7 form a saturated or unsaturated ring; at least two of R9, R10, R11 and R12 form a saturated or unsaturated ring; each L1 and L2 is independently selected from the group consisting of a single bond, substituted and unsubstituted C1-30 alkylene, substituted and unsubstituted C6-30 arylene, and substituted and unsubstituted C3-30 heteroarylene; each Ar1 and Ar2 is independently selected from the group consisting of substituted and unsubstituted C6-30 aryl, and substituted and unsubstituted C3-30 heteroaryl; each p and q is independently an integer ranging from 1 to 5; and each m and n is independently an integer ranging from 0 to 4, wherein both m and n are not 0. An organic light emitting diode(OLED) comprises: a first electrode; a second electrode; and an organic layer between the first and second electrodes, the organic layer comprising the compound of the formula(1). The organic light emitting diode further comprises a hole injection layer, a hole transport layer, an emissive layer and an electron injection layer between the first and second electrodes.

Description

Imidazopyridine-based compound and an organic light-emitting device employing an organic layer comprising the same

The present invention relates to an organic light emitting device having an imidazopyridine-based compound and an organic film including the same, and more particularly, to an organic light-emitting device having an imidazopyridine-based compound and an organic film including the same suitable for use in an electron transport layer of an organic light-emitting device. It relates to an element. An organic light emitting device having an organic film including an imidazopyridine-based compound according to the present invention may have low driving voltage, high efficiency, high brightness, long life, and low power consumption.

Light emitting diodes are self-luminous devices that have a wide viewing angle, excellent contrast, and fast response time.

Light emitting devices are classified into inorganic light emitting diodes and organic light emitting diodes (OLEDs) according to materials for forming an emitting layer. Herein, the organic light emitting device has an advantage of excellent luminance, driving voltage, and response speed, and multicoloring, compared to the inorganic light emitting device.

A general organic light emitting device has an anode formed on the substrate, and a hole transport layer, a light emitting layer, an electron transport layer and a cathode are sequentially formed on the anode. Here, the hole transport layer, the light emitting layer and the electron transport layer are organic thin films made of an organic compound.

The driving principle of the organic light emitting device having the structure as described above is as follows.

When a voltage is applied between the anode and the cathode, holes injected from the anode move to the light emitting layer via the hole transport layer, and holes injected from the cathode move to the light emitting layer via the electron transport layer. Carriers such as holes and electrons recombine in the emission layer to generate excitons. The excitons change from the excited state to the ground state, whereby the fluorescent molecules in the light emitting layer emit light to emit light. Heteroaromatic compounds, such as oxadiazoles, thiadiazoles, or pyrimidines, etc. are known as a double electron transport layer formation material (refer US patent 6,559,256).

However, the conventional organic light emitting device did not have satisfactory driving voltage, brightness, current density, power efficiency, lifespan characteristics, and the like, and thus, improvement thereof is necessary.

The technical problem to be achieved by the present invention is to provide an imidazopyridine-based compound having a high electron transport ability to solve the above problems.

Another object of the present invention is to provide an organic light emitting device having high efficiency, low voltage, high brightness and long life using the imidazopyridine-based compound.

In order to achieve the above technical problem, a first aspect of the present invention provides an imidazopyridine-based compound having Formula 1 below:

<Formula 1>

In Formula 1,

R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ , R ₁₁ and R ₁₂ independently of one another, hydrogen, a halogen atom, a hydroxy group, a cyano group, A substituted or unsubstituted C ₁ -C ₃₀ alkyl group, a substituted or unsubstituted C ₁ -C ₃₀ alkoxy group, a substituted or unsubstituted C ₁ -C ₃₀ acyl group, a substituted or unsubstituted C ₂ -C ₃₀ alkenyl group , A substituted or unsubstituted C ₂ -C ₃₀ alkynyl group, a substituted or unsubstituted C ₆ -C ₃₀ aryl group, or a substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group, and R ₄ to R ₇ Two or more adjacent ones may combine with each other to form a saturated or unsaturated ring, and two or more adjacent ones of R ₉ to R ₁₂ may combine with each other to form a saturated or unsaturated ring;

L ₁ and L ₂ are each independently a single bond, a substituted or unsubstituted C ₁ -C ₃₀ alkylene group, a substituted or unsubstituted C ₆ -C ₃₀ arylene group or a substituted or unsubstituted C ₃ -C ₃₀ hetero Arylene group;

Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C ₆ -C ₃₀ aryl group or a substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group;

p and q are, independently from each other, an integer from 1 to 5;

m and n, independently of each other, are integers from 0 to 4, except that m and n are both zero.

In order to achieve another technical problem of the present invention, a second aspect of the present invention, the first electrode; Second electrode; And an organic layer including the imidazopyridine-based compound between the first electrode and the second electrode.

The imidazopyridine-based compound having Formula 1 has excellent electron transporting ability, and the organic light emitting device having an organic film including the same may have a low driving voltage, high current density, high brightness, high efficiency, and long life.

The imidazopyridine-based compound having Formula 1 of the present invention is excellent in electron transport performance, the organic light emitting device having an organic film including the same, it may have a low driving voltage, high brightness, high efficiency, low power consumption and long life.

 Although the present invention has been described with reference to the synthesis examples and examples, this is merely illustrative, and those skilled in the art to which the present invention pertains various modifications and equivalent other embodiments. Will understand. Therefore, the true technical protection scope of the present invention will be defined by the technical spirit of the appended claims.

The imidazopyridine-based compound according to the present invention has the formula (1) as described above. According to Chemical Formula 1, an imidazopyridine ring is connected to at least one of 1 to 8 positions except for the 9 or 10 position of the anthracene ring with a linking group L ₁ or L ₂ interposed therebetween.

This is because the 9 and 10 positions of the anthracene ring are structurally weak points, and when the groups having a specific function are substituted at the 9 and 10 positions of the anthracene ring, the groups are separated by heat, oxygen, moisture, and the like. This is because it can be easily separated from the anthracene ring. For example, when a deficient imidazopyridine ring is connected to the 9 and 10 positions of the anthracene ring, a process for forming an organic layer of an organic light emitting device (for example, a vapor deposition method) or organic light emission The imidazopyridine ring may be easily separated from the anthracene ring due to heat generated when driving the device, and may cause device property deterioration. However, in the compounds according to the present invention, aromatic rings such as aryl groups or heteroaryl groups are introduced at positions 9 and 10 of the anthracene ring, and imidazo deficient in electrons at positions 1 to 8 of the anthracene ring. As the pyridine ring is introduced, the structural stability and electron mobility of the compound can be improved.

In Formula 1, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ , R ₁₁ and R ₁₂ are independently of each other, hydrogen, a halogen atom, Hydroxy group, cyano group, substituted or unsubstituted C ₁ -C ₃₀ alkyl group, substituted or unsubstituted C ₁ -C ₃₀ alkoxy group, substituted or unsubstituted C ₁ -C ₃₀ acyl group, substituted or unsubstituted C ₂ It can be a -C ₃₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₃₀ alkynyl group, a substituted or unsubstituted C ₆ -C ₃₀ aryl group, or a substituted or unsubstituted C ₃ -C ₃₀ heteroaryl. In this case, two or more adjacent to each other of R ₄ to R ₇ may be bonded to each other to form a saturated or unsaturated ring, and two or more adjacent to each other of R ₉ to R ₁₂ may be bonded to each other to form a saturated or unsaturated ring. .

For example, R ₁ to R ₁₂ are each independently hydrogen, a substituted or unsubstituted C ₁ -C ₁₀ alkyl group, a substituted or unsubstituted C ₂ -C ₁₀ alkenyl group, a substituted or unsubstituted C _6- It may be a C ₁₂ aryl group, or a C ₃ -C ₁₂ heteroaryl group.

In addition, two or more adjacent to each other of the R ₄ to R ₇ or two or more adjacent to each other of the R ₉ to R ₁₂ may combine to form a substituted or unsubstituted C ₆ -C ₁₂ aromatic ring, but is not limited thereto. no.

In Formula 1, L ₁ and L ₂ are each independently a single bond, a substituted or unsubstituted C ₁ -C ₃₀ alkylene group, a substituted or unsubstituted C ₆ -C ₃₀ arylene group or a substituted or unsubstituted C _It may be a ₃ -C ₃₀ heteroarylene group.

For example, L ₁ and L ₂ may be each independently a substituted or unsubstituted C ₆ -C ₁₂ arylene group, or a substituted or unsubstituted C ₃ -C ₁₂ heteroarylene group, but is not limited thereto. no.

In Formula 1, Ar ₁ and Ar ₂ may be each independently a substituted or unsubstituted C ₆ -C ₃₀ aryl group or a substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group.

For example, Ar ₁ and Ar ₂ may be each independently a substituted or unsubstituted C ₆ -C ₁₂ aryl group, or a substituted or unsubstituted C ₃ -C ₁₂ heteroaryl group.

In Formula 1, p and q are each independently an integer of 1 to 5, preferably an integer of 1 to 3. That is, there L ₁ or L ₂ include at least one already connected to an imidazo pyridine ring, which is to be selected according to the structure formula of L ₁ or L _2.

In Formula 1, m and n may be each independently an integer of 0 to 4. In this case, the case where m and n are both 0 is excluded. That is, at least one or more of positions 1 to 8 of the anthracene ring of the imidazopyridine-based compound according to the present invention must be connected to the imidazopyridine ring.

For example, m may be 0 and n may be 1. Alternatively, m and n may both be 1.

Specific examples of the unsubstituted C ₁ -C ₃₀ alkyl group in the general formula (1) of the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like, and at least one of the alkyl groups The hydrogen atom is a halogen atom, hydroxy group, nitro group, cyano group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, or C ₁ -C ₃₀ alkyl group, C ₁ To be substituted with a -C ₃₀ alkenyl group, a C ₁ -C ₃₀ alkynyl group, a C ₆ -C ₃₀ aryl group, a C ₇ -C ₂₀ arylalkyl group, a C ₂ -C ₂₀ heteroaryl group or a C ₃ -C ₃₀ heteroarylalkyl group Can be.

Specific examples of the unsubstituted C ₁ -C ₃₀ alkoxy group in the general formula (1) of the present invention include methoxy, ethoxy, phenyloxy, cyclohexyloxy, naphthyloxy, isopropyloxy, diphenyloxy, and the like. At least one hydrogen atom of these alkoxy groups may be substituted with the same substituent as in the alkyl group described above.

Specific examples of the unsubstituted C ₁ -C ₃₀ acyl group in the general formula (1) of the present invention, acetyl, ethylcarbonyl, isopropylcarbonyl, phenylcarbonyl, naphthylenecarbonyl, diphenylcarbonyl, cyclohexylcarbonyl And at least one hydrogen atom of these acyl groups may be substituted with the same substituent as in the alkyl group described above.

The unsubstituted C ₂ -C ₃₀ alkenyl group in the general formula (1) of the present invention means that it contains a carbon double bond in the middle or the end of the alkyl group as defined above. Examples are ethylene, propylene, butylene, hexylene and the like. At least one hydrogen atom of these alkenyl groups may be substituted with the same substituent as in the alkyl group described above.

The unsubstituted C ₂ -C ₃₀ alkynyl group in the general formula (1) of the present invention means that it contains a carbon triple bond in the middle or the end of the alkyl group as defined above. Examples include acetylene, propylene, phenylacetylene, naphthylacetylene , Isopropylacetylene, t-butylacetylene, diphenylacetylene and the like. At least one hydrogen atom of these alkynyl groups may be substituted with the same substituent as in the alkyl group described above.

An unsubstituted C ₆ -C ₃₀ aryl group of Formula 1 of the present invention means a carbocyclic aromatic system having 6 to 30 carbon atoms including one or more aromatic rings, wherein the one or more rings are fused to each other or a single bond. And so on. At least one hydrogen atom of the aryl group may be substituted with the same substituent as in the alkyl group described above.

Examples of the substituted or unsubstituted C ₆ -C ₃₀ aryl group include a phenyl group, a C ₁ -C ₁₀ alkylphenyl group (eg, ethylphenyl group), a C ₁ -C ₁₀ alkylbiphenyl group (eg, ethylbiphenyl group ), Halophenyl groups (e.g., o-, m- and p-fluorophenyl groups, dichlorophenyl groups), dicyanophenyl groups, trifluoromethoxyphenyl groups, o-, m-, and p-tolyl groups, o-, m- and p-cumenyl groups, mesityl groups, phenoxyphenyl groups, (α, α-dimethylbenzene) phenyl groups, (N, N'-dimethyl) aminophenyl groups, (N, N'-diphenyl) aminophenyl groups, penteres Neyl group, indenyl group, naphthyl group, halonaphthyl group (e.g. fluoronaphthyl group), C ₁ -C ₁₀ alkylnaphthyl group (e.g. methylnaphthyl group), C ₁ -C ₁₀ alkoxynaphthyl group (e.g. For example, a methoxy naphthyl group), anthracenyl group, azurenyl group, heptarenyl group, acenaphthylenyl group, phenenalenyl group, fluorenyl group, anthraquinolyl group, methyl anthryl group, phenanthryl group, triphenylene group , Pyrenyl, Risenyl group, ethyl-crisenyl group, pisenyl group, perylenyl group, chloroperylenyl group, pentaphenyl group, pentasenyl group, tetraphenylenyl group, hexaphenyl group, hexasenyl group, rubisenyl group, coronyl group, A trinaphthyleneyl group, a heptaphenyl group, a heptacenyl group, a pyrantrenyl group, an obarenyl group, etc. are mentioned.

An unsubstituted C ₃ -C ₃₀ heteroaryl group of the general formula (1) of the present invention means a system consisting of one or more aromatic rings containing at least one heteroatom selected from N, O, P or S and the remaining ring atom is C, The one or more aromatic rings may be fused to each other or connected through a single bond or the like. At least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as in the alkyl group described above.

Examples of the unsubstituted C ₃ -C ₃₀ heteroaryl group in the general formula (1) include pyrazolyl group, imidazolyl group, oxazolyl group, thiazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, pyri A diyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, a carbazolyl group, an indolyl group, a quinolinyl group, an isoquinolinyl group, etc. are mentioned.

More specifically, in Formula 1, R ₁ to R ₁₂ are each independently hydrogen, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ haloalkyl group, C ₂ -C ₁₀ alkenyl group, C ₂ -C ₁₀ haloalke It may be a silyl group, a phenyl group, a halophenyl group, a C ₁ -C ₁₀ alkylphenyl group, a C ₁ -C ₁₀ alkoxyphenyl group, a naphthyl group, a halonaphthyl group, a C ₁ -C ₁₀ alkylnaphthyl group, or a C ₁ -C ₁₀ alkoxynaphthyl group However, the present invention is not limited thereto.

In Formula 1, L ₁ and L ₂ are each independently a phenylene group, a halophenylene group, a C ₁ -C ₁₀ alkylphenylene group, a C ₁ -C ₁₀ alkoxyphenylene group, a naphthylene group, a halonaphthylene group , C ₁ -C ₁₀ alkyl naphthylene group, or C ₁ -C ₁₀ alkoxy naphthylene group, but is not limited thereto.

Meanwhile, in Formula 1, Ar ₁ and Ar ₂ are each independently a phenyl group, a halophenyl group, a C ₁ -C ₁₀ alkylphenyl group, a C ₁ -C ₁₀ alkoxyphenyl group, a naphthyl group, a halonaphthyl group, C ₁ -C ₁₀ an alkyl naphthyl group, a C ₁ -C ₁₀ alkoxy-naphthyl group, a pyridinyl group, a halo-pyridinyl group, C ₁ -C ₁₀ alkyl pyridinyl group, C ₁ -C ₁₀ alkoxy pyridinyl group, quinolinyl group, a halo-quinolinyl group , C ₁ -C ₁₀ alkylquinolinyl group, C ₁ -C ₁₀ alkoxyquinolinyl group, isoquinolinyl group, haloisoquinolinyl group, C ₁ -C ₁₀ alkylisoquinolinyl group, or C ₁ -C ₁₀ alkoxy It may be an isoquinolinyl group, but is not limited thereto.

More specifically, the imidazopyridine-based compound according to the present invention may have the following Chemical Formula 1a, 1b, 1c or 1d, but is not limited thereto.

<Formula 1a>

<Formula 1b>

<Formula 1c>

<Formula 1d>

In Formulas 1a, 1b, 1c, and 1d, R ₃ to R ₁₂ , Ar _1, and Ar ₂ may be described in detail above.

According to an embodiment of the present invention, the compound having Formula 1 may be Compound 1 to 11 having the following structure, but is not limited thereto:

<Compound 1> <Compound 2>

<Compound 3> <Compound 4>

<Compound 5>

<Compound 6>

<Compound 7> <Compound 8>

<Compound 9> <Compound 10>

<Compound 11>

The imidazopyridine-based compound having Formula 1 may be prepared using various known methods, which can be easily recognized by those skilled in the art.

For example, the imidazopyridine-based compound having Formula 1 may be obtained by reacting a compound having Formula 2 with a compound having Formula 3 and / or a compound having Formula 4:

<Formula 2>

<Formula 3> <Formula 4>

In the above formulae, the definitions for R ₁ to R ₁₂ , L ₁ , L ₂ , Ar ₁ , Ar ₂ , p, q, n and m may be referred to the foregoing. The manufacturing method may be one using a Suzuki reaction.

The imidazopyridine-based compound having Formula 1 as described above may be included in the organic film of the organic light emitting device. Therefore, the organic light emitting device according to the present invention, the first electrode; Second electrode; And an organic layer including an imidazopyridine-based compound having Formula 1 between the first electrode and the second electrode. Preferably, the organic layer may be an electron transport layer. The organic light emitting diode may further include at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer. For example, the organic light emitting device according to the present invention may further include a hole injection layer, a hole transport layer, a light emitting layer, and an electron injection layer when the organic film including the imidazopyridine compound having Formula 1 is an electron transport layer. have. In addition, when the light emitting layer is formed using a phosphorescent material, various modifications are possible, such as a hole blocking layer may be further included.

More specifically, an embodiment of the organic light emitting device according to the present invention refers to FIG. 1. The organic light emitting device of FIG. 1 has a structure of a first electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / second electrode. Alternatively, the organic light emitting device according to the present invention has a structure consisting of a first electrode / hole injection layer / light emitting layer / electron transport layer / electron injection layer / second electrode, or the first electrode / hole injection layer / hole transport layer / light emitting layer / It may have a structure consisting of a hole blocking layer / electron transport layer / electron injection layer / second electrode, but is not limited thereto. In this case, the electron transport layer may include a compound having Formula 1.

The light emitting layer of the organic light emitting device according to the present invention may include a phosphorescent or fluorescent dopant including red, green, blue or white. Among these, the phosphorescent dopant may be an organometallic compound including at least one element selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, and Tm.

Hereinafter, a method of manufacturing an organic light emitting diode according to the present invention will be described with reference to the organic light emitting diode illustrated in FIG. 1.

First, a first electrode material having a high work function on the substrate is formed by a deposition method or a sputtering method to form a first electrode. The first electrode may be an anode or a cathode. Herein, a substrate used in a conventional organic light emitting device is used, and a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness is preferable. Indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, are used as the material for the first electrode.

Next, the hole injection layer HIL may be formed on the first electrode by using various methods such as vacuum deposition, spin coating, casting, and LB.

In the case of forming the hole injection layer by vacuum deposition, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the hole injection layer, and the like. It is preferable that a vacuum degree of 10 ^-8 to 10 ^-3 torr, a deposition rate of 0.01 to 100 mW / sec, and a film thickness are usually appropriately selected in the range of 10 mV to 5 m.

In the case of forming the hole injection layer by spin coating, the coating conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the desired hole injection layer, but the coating speed is about 2000 rpm to 5000 rpm. , The heat treatment temperature for removing the solvent after coating is preferably selected in the temperature range of about 80 ℃ to 200 ℃.

The hole injection layer material is not particularly limited and may be arbitrarily selected from known hole injection layer materials. For example, TCTA, m-MTDATA, m-MTDAPB, which are phthalocyanine compounds such as copper phthalocyanine disclosed in US Pat. No. 4,356,429, or starburst type amine derivatives described in Advanced Material, 6, p.677 (1994), Pani / DBSA (Polyaniline / Dodecylbenzenesulfonic acid: polyaniline / dodecylbenzenesulfonic acid) or PEDOT / PSS (Poly (3,4-ethylenedioxythiophene) / Poly (4-styrenesulfonate): poly (3,4-ethylene) Deoxythiophene) / poly (4-styrenesulfonate)), Pani / CSA (Polyaniline / Camphor sulfonic acid: polyaniline / camphorsulfonic acid) or PANI / PSS (Polyaniline) / Poly (4-styrenesulfonate): polyaniline) / poly ( 4-styrenesulfonate)) and the like can be used.

The hole injection layer may have a thickness of about 100 kPa to 10000 kPa, preferably 100 kPa to 1000 kPa. This is because when the thickness of the hole injection layer is less than 100 kW, the hole injection characteristic may be degraded. When the thickness of the hole injection layer is more than 10000 kW, the driving voltage may increase.

Next, a hole transport layer (HTL) may be formed on the hole injection layer by using various methods such as vacuum deposition, spin coating, cast, and LB. In the case of forming the hole transport layer by vacuum deposition and spinning, the deposition conditions and coating conditions vary depending on the compound used, and are generally selected from the ranges of conditions substantially the same as those of forming the hole injection layer.

The hole transport layer material is not particularly limited, and may be selected arbitrarily from known hole transport layer materials. For example, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1-biphenyl] -4 Conventional amine derivatives having aromatic condensed rings such as 4'-diamine (TPD), N, N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine (? -NPD), and the like are used. do.

α-NPD

The hole transport layer may have a thickness of about 50 kPa to 1000 kPa, preferably 100 kPa to 600 kPa. This is because when the thickness of the hole transport layer is less than 50 kV, hole transport characteristics may be reduced, and when the thickness of the hole transport layer exceeds 1000 kW, the driving voltage may increase.

Next, the light emitting layer EML may be formed on the hole transport layer by using a vacuum deposition method, a spin coating method, a cast method, an LB method, or the like. When the light emitting layer is formed by vacuum deposition or spin coating, the deposition conditions vary depending on the compound used, but are generally selected from the ranges of conditions almost the same as that of forming the hole injection layer.

The light emitting layer may be formed using various known light emitting materials. The light emitting layer may be formed using a known host and a dopant, and in the case of a dopant, both a known fluorescent dopant and a known phosphorescent dopant may be used.

For example, Alq ₃ , CBP (4,4'-N, N'-dicarbazole-biphenyl), PVK (poly (n-vinylcarbazole)) or DSA (distyrylarylene) may be used as the host. But it is not limited thereto.

In the case of dopants, the fluorescent dopants may be IDE102 or IDE105, available from Idemitsu, and Ir (ppy) ₃ (ppy is an acronym for phenylpyridine) (green), (4, 6-F2ppy) ₂ Irpic (Reference: Chihaya Adachi etc. Appl . Phys . Lett ., 79, 2082-2084, 2001), TEB002 from Cobion, Platinum (II) octaethylporphyrin (PtOEP), a compound having the formula (See Korean Patent Publication No. 2005-0078472), Firpric, TBPe and the like can be used, but is not limited thereto.

<Formula 5> Firpic

The content of the dopant is preferably 0.1 to 20 parts by weight, particularly 0.5 to 12 parts by weight, based on 100 parts by weight of the light emitting layer forming material (ie, the total weight of the host and the dopant is 100 parts by weight). If the content of the dopant is less than 0.1 parts by weight, the effect of the addition of the dopant is insignificant, and if it exceeds 20 parts by weight, concentration phosphorescence or fluorescence, such as concentration quenching (quenching) is not preferable because it occurs.

The thickness of the light emitting layer may be about 100 kPa to 1000 kPa, preferably 200 kPa to 600 kPa. This is because, when the thickness of the light emitting layer is less than 100 kW, the light emission characteristics may be reduced, and when the thickness of the light emitting layer exceeds 1000 kW, the driving voltage may increase.

When the light emitting layer includes a phosphorescent dopant, a hole blocking layer HBL may be formed on the light emitting layer to prevent the triplet excitons or holes from diffusing into the electron transport layer (not shown in FIG. 1). The hole blocking layer material that can be used at this time is not particularly limited, and may be selected arbitrarily from known hole blocking layer materials. For example, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or a hole blocking material described in JP 11-329734 (A1), Balq, BCP, or the like can be used.

The hole blocking layer may have a thickness of about 50 kPa to 1000 kPa, preferably 100 kPa to 300 kPa. This is because when the thickness of the hole blocking layer is less than 50 kV, the hole blocking property may be deteriorated. When the thickness of the hole blocking layer is more than 1000 kV, the driving voltage may increase.

Next, the electron transport layer (ETL) is formed using various methods such as vacuum deposition, spin coating, and casting. When the electron transport layer is formed by the vacuum deposition method or the spin coating method, the conditions vary depending on the compound used, but are generally selected from the ranges of conditions almost the same as that of the formation of the hole injection layer.

As the electron transporting material, an imidazopyridine-based compound having Formula 1 as described above may be used. Alternatively, quinoline derivatives, especially known materials such as tris (8-quinolinorate) aluminum (Alq ₃ ), TAZ, and the like may also be used.

The electron transport layer may have a thickness of about 100 kPa to 1000 kPa, preferably 100 kPa to 500 kPa. This is because when the thickness of the electron transport layer is less than 100 kV, the electron transport characteristic may be degraded, and when the thickness of the electron transport layer exceeds 1000 kW, the driving voltage may increase.

In addition, an electron injection layer (EIL), which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer.

As the electron injection layer, any material known as an electron injection layer forming material such as LiF, NaCl, CsF, Li ₂ O, BaO, or the like can be used. The deposition conditions and coating conditions of the electron injection layer vary depending on the compound used, but are generally selected from a range of conditions substantially the same as the formation of the hole injection layer.

The electron injection layer may have a thickness of about 1 kPa to 100 kPa, preferably 5 kPa to 90 kPa. This is because, when the thickness of the electron injection layer is less than 1 kW, the electron injection characteristic may be deteriorated, and when the thickness of the electron injection layer exceeds 100 kW, the driving voltage may increase.

Finally, the second electrode may be formed on the electron injection layer by using a vacuum deposition method or a sputtering method. The second electrode may be used as a cathode or an anode. As the metal for forming the second electrode, a metal, an alloy, an electrically conductive compound having a low work function, and a mixture thereof may be used. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. Can be mentioned. In addition, it is also possible to use a transparent cathode using ITO, IZO to obtain a top light emitting device.

Hereinafter, examples of the synthesis of the compounds 1 to 10 according to the present invention and an embodiment related to the manufacture of an organic light emitting device having an organic film including the same are specifically illustrated, but the present invention is not limited to the following synthesis examples and examples. .

EXAMPLE

Synthesis Example  1: Synthesis of Compound 1

Compound 1 was synthesized according to the reaction route of Scheme 1 below:

Synthesis of Intermediate 1a

Copper bromide (10 g, 44 mmol) and 2-aminoanthraquinone (8 g, 35.8 mmol) were put in 250 ml of bromic acid, and it heated at 65 degreeC. After the generation of gas was cooled to room temperature, the reaction solution was added to 20% hydrochloric acid aqueous solution (1000ml), and extracted with dichloromethane. The residual moisture of the organic layer was removed with anhydrous magnesium sulfate, and dried under reduced pressure. Separation by column chromatography (dichloromethane: normalhexane = 4: 1) afforded 7.7 g of intermediate 1a (yield 75%).

Synthesis of Intermediate 1b

The intermediate 1a (10 g, 34.8 mmol) was added to 100 ml of THF dried under a nitrogen atmosphere, and the temperature was lowered to −78 ° C., followed by slowly adding 2-naphthyl magnesium bromide (0.5 M, 10 mmol). The temperature was raised to room temperature and stirred for 3 hours. An aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed. The resulting mixture was dissolved in a small amount of ethyl ether, and then petroleum ether was added and stirred for several hours to obtain a solid compound. This was filtered and dried in vacuo to give 17.6 g of dinaphthyldialcohol.

Disperse the dinaphthyldialcohol (17.6g, 32.4mmol) in 200ml of acetic acid under nitrogen atmosphere, add potassium iodide (53.4g, 330mmol), sodium hypophosphite hydrate (58g, 660mmol) and then stir reflux for 3 hours It was. After cooling to room temperature, the mixture was filtered, washed with water and methanol and dried in vacuo to obtain 11.3 g of pale yellow intermediate 1b.

Synthesis of Intermediate 1c

The intermediate 1b (5 g, 9.81 mmol) was dissolved in 70 ml of THF dried under a nitrogen atmosphere, and butyllithium (4.7 ml, 11.8 mmol) was added dropwise at -78 ° C. After stirring for one hour at the same temperature, trimethylborate (2.20ml, 29.4mmol) was added. The temperature was raised to room temperature, and after 1 hour, an aqueous 2N hydrochloric acid solution was added and stirred for 3 hours. The resulting solid compound was filtered with washing with toluene to give a pale yellow intermediate 1c (3.27 g, 70% yield).

Synthesis of Intermediate 1d

2-aminopyridine (3.39 g, 35.98 mmol) and 2,4'-dibromoacetophenone (10 g, 35.98 mmol) were dissolved in ethanol (150 ml) and refluxed for 12 hours. Cooling to room temperature gave a white solid, which was washed with a saturated aqueous NaHCO ₃ solution. The residual moisture of the organic layer was removed with anhydrous magnesium sulfate, dried under reduced pressure, and recrystallized (dichloromethane / normal hexane) to obtain an intermediate 1d having a plate crystal form (8.02 g, 82% yield).

Synthesis of Compound 1

The intermediate 1c (1.85g, 3.90mmol) and the intermediate 1d (1g, 3.90mmol) were added to a mixed solvent of potassium carbonate (2.7g, 19.5mmol) solution and THF, and stirred with Pd (PPh ₃ ) ₄ (225mg, 0.196mmol). ) Was refluxed for 6 hours. After cooling to room temperature, the resulting solid compound was filtered with washing with water, ethanol and THF to obtain Compound 1 in the form of a pale yellow powder (1.73 g, 71% yield).

1 H NMR (400 MHz, CDCl ₃ ) 8.13-8.04 (7H), 8.01 (1H), 7.97-7.92 (4H), 7.86-7.82 (2H), 7.75 (2H), 7.71-7.58 (10H), 7.32 (2H) , 7.15 (1 H), 6.75 (1 H)

Synthesis Example  2: Synthesis of Compound 4

Compound 4 was synthesized according to the reaction route of Scheme 2:

Synthesis of Intermediate 4d

5 g (18.3 mmol) of imidazo pyridine compound 1d (see Synthesis Example 1 above) and 4.12 g (18.3 mmol) of NIS (N-iodine succinic acid) are dissolved in an acetonitrile solvent, stirred at room temperature for 1 hour, and then 100 ml of chloroform is added thereto. After washing with% aqueous sodium hydroxide solution, washed with saturated aqueous sodium thiosulfate solution and water, dried over anhydrous magnesium sulfate, filtered, and then the solvent was removed. The obtained solid was washed with methanol and filtered to obtain 5.8 g (yield 79%) of iodine compounds. The obtained iodine compound and 1.76 g (14.5 mmol) of phenylboronic acid were added to a mixed solvent of potassium carbonate (10 g) aqueous solution and THF, and stirred with Pd (PPh 3) 4 (335 mg), followed by reflux for 24 hours. The reaction solution was extracted with dichloromethane, the residual moisture of the organic layer was removed with anhydrous magnesium sulfate, and dried under reduced pressure. Separation by column chromatography (ethyl acetate: normal hexane = 2: 3) gave 2.93 g (yield 58%) of intermediate 4d.

Synthesis of Compound 4

Compound 4 was prepared in the same manner as in the preparation of compound 1 of Synthesis Example 1, except that Intermediate 4d was used instead of Intermediate 1d of Synthesis Example 1. Suzuki reaction with 10 g (21.08 mmol) of Intermediate 1c and 6.69 g (19.16 mmol) of 4d yielded 9.72 g (73% yield) of Compound 4 in the form of a pale yellow powder. 1 H NMR (400 MHz, CDCl ₃ ) 8.08 (1 H), 8.03-8.01 (2H), 7.97-7.88 (3H), 7.81 (1H), 7.74-7.58 (12), 7.51-7.40 (10), 7.29-7.23 (3H), 7.15 (1H), 6.69 (1H)

Synthesis Example  3: Synthesis of Compound 7

Compound 7 was synthesized according to the reaction route of Scheme 3:

Compound 7 was prepared in the same manner as in Synthesis Example 1, except that Intermediate 7d was obtained by using 1-aminoisoquinoline instead of 2-aminopyridine in the synthesis of Intermediate 1d of Synthesis Example 1 Was prepared. Suzuki reaction with 10 g (21.08 mmol) of Intermediate 1c and 6.19 g (19.16 mmol) of 7d afforded 9.03 g (70% yield) of Compound 7 in the form of a pale yellow powder.

 1 H NMR (400 MHz, CDCl 3) 8.69 (1H), 8.12 (2H), 8.07-8.02 (5H), 7.99-7.95 (4H), 7.89-7.84 (2H), 7.79-7.75 (3H), 7.71-7.65 (4H ), 7.64-7.54 (8H), 7.33 (2H), 7.02 (1H)

Synthesis Example  4: synthesis of compound 3

Compound 3 was synthesized according to the reaction route of Scheme 4:

Except for the use of 2,4'-dibromopropiophenone instead of 2,4'-dibromoacetophenone in the synthesis of the intermediate 1d of Synthesis Example 1 to obtain the intermediate 3d, Compound 3 was prepared in the same manner as in Synthesis example 1. Suzuki reaction with 5 g (10.54 mmol) of Intermediate 1c and 2.75 g (9.58 mmol) of 3d gave 4.15 g (68% yield) of Compound 3 in the form of a pale yellow powder.

1 H NMR (400 MHz, CDCl ₃ ) 8.12 (2H), 8.07-8.02 (5H), 7.97-7.95 (2H), 7.89-7.84 (2H), 7.80-7.71 (4H), 7.70-7.66 (3H), 7.63- 7.60 (7H), 7.32 (2H), 7.15 (1H), 6.83 (1H), 2.62 (3H)

Synthesis Example  5: synthesis of compound 2

Compound 2 was synthesized according to the reaction route of Scheme 5 below:

Using the same method as in Synthesis Example 1, except that Intermediate 2c was obtained by using phenylmagnesium bromide instead of 2-naphthyl magnesium bromide in the synthesis of Intermediates 1b and 1c of Synthesis Example 1 Compound 2 was prepared. Suzuki reaction with 5 g (13.36 mmol) of Intermediate 2c and 3.32 g (12.15 mmol) of 1d gave 4.64 g (yield 73%) of Compound 2 in the form of a pale yellow powder.

1 H NMR (400 MHz, CDCl ₃ ) 8.11 (1H), 7.99 (2H), 7.95 (1H), 7.86 (1H), 7.64 (1H), 7.73-7.70 (2H), 7.69 (1H), 7.66-7.61 (7H ), 7.58 (2H), 7.56-7.50 (4H), 7.34 (2H), 7.17 (1H), 6.78 (1H)

Synthesis Example  6: synthesis of compound 11

Compound 11 was synthesized according to the reaction route of Scheme 6 below:

Compound 11 was obtained by obtaining intermediates 2c and 3d, respectively, in the same manner as in Synthesis Example 5 and Synthesis Example 4. Suzuki reaction with 5 g (13.36 mmol) of Intermediate 2c and 3.49 g (12.15 mmol) of 3d gave 4.72 g (72% yield) of Compound 11 in the form of a pale yellow powder.

1 H NMR (400 MHz, CDCl ₃ ) 7.97 (1H), 7.91 (1H), 7.85 (2H), 7.80 (1H), 7.73-7.70 (2H), 7.69 (1H), 7.66-7.61 (7H), 7.58 (2H ), 7.56-7.50 (4H), 7.34 (2H), 7.19 (1H), 6.86 (1H), 2.67 (3H)

Example  One

As an anode, Corning's 15 Ω / cm 2 (1200 kW) ITO glass substrate was cut into 50 mm x 50 mm x 0.7 mm in size and ultrasonically cleaned for 5 minutes in isopropyl alcohol and pure water, followed by UV ozone cleaning for 30 minutes. M-MTDATA was vacuum deposited on the substrate to form a hole injection layer having a thickness of 750 μs, and α-NPD was vacuum deposited on the hole injection layer to form a 150 μm thick hole transport layer. A light emitting layer having a thickness of 300 μs was formed on the hole transport layer by using 97 wt% of DSA as a host and 3 wt% of TBPe as a dopant. Compound 1 obtained from Synthesis Example 1 was vacuum deposited on the emission layer to form an electron transport layer having a thickness of 200 μs. LiF was vacuum deposited on the electron transport layer to form an electron injection layer having a thickness of 80 mV, and Al was vacuum deposited to form a cathode having a thickness of 3000 mW, thereby completing the organic light emitting device.

Example  2 to 6

In the above Example 1, except that Compounds 4, 7, 3, 2, and 11 obtained from Synthesis Examples 2 to 6 were used instead of Compound 1 obtained from Synthesis Example 1 as the electron transporting layer forming material, respectively. An organic light emitting device was completed in the same manner as in Example 1.

Comparative example

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Alq3 (8-hydroxyquinoline aluminum complex) was used instead of Compound 1 obtained from Synthesis Example 1 as an electron transporting layer forming material. Completed.

Evaluation example

For the organic light emitting diodes of Examples 1 to 6 and the organic light emitting diodes of Comparative Examples, current density (mA / cm ² ), driving voltage (V), luminance (cd / m ² ), and efficiency (Im / W) were measured. It was evaluated using PR650 (Spectroscan) Source Measurement Unit. (Produced by PhotoResearch), and the results are shown in Table 1 below. In particular, voltage-current density graphs and luminance-efficiency graphs of the organic light emitting diodes of Examples 1 to 6 and the organic light emitting diodes of Comparative Examples are shown in FIGS. 2 and 3, respectively.

division Electron transport layer forming material Current density (mA / cm ² ) Drive voltage (V) Luminance (cd / m ² ) Efficiency (Im / W) Example 1 Compound 1 10 3.4 780 7.25 Example 2 Compound 4 10 3.6 774 6.67 Example 3 Compound 7 10 5.1 996 6.06 Example 4 Compound 3 10 4.0 1049 8.12 Example 5 Compound 2 10 3.7 868 7.38 Example 6 Compound 11 10 3.8 905 7.54 Comparative example Alq3 10 5.9 581 2.9

As can be seen from Tables 1, 2 and 3, the organic light emitting diodes of Examples 1 to 6 have improved current density, driving voltage, brightness, and efficiency characteristics than the organic light emitting diode of Comparative Example. Therefore, it can be seen that an organic light emitting device having an organic film including an imidazopyridine compound having the formula (1) according to the present invention is capable of driving higher brightness, higher efficiency, lower voltage, and longer life than conventional organic light emitting devices.

1 is a view schematically showing the structure of an embodiment of an organic light emitting device according to the present invention,

2 is a graph showing the voltage-current density characteristics of the organic light emitting device and the embodiments of the organic light emitting device according to the present invention,

3 is a graph illustrating luminance-efficiency characteristics of the organic light emitting diode according to the embodiments and the organic light emitting diode according to the present invention.

Claims (16)

An imidazopyridine-based compound having the following Chemical Formula 1: <Formula 1>

In Formula 1, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ , R ₁₁ and R ₁₂ independently of one another, hydrogen, a halogen atom, a hydroxy group, a cyano group, A substituted or unsubstituted C ₁ -C ₃₀ alkyl group, a substituted or unsubstituted C ₁ -C ₃₀ alkoxy group, a substituted or unsubstituted C ₁ -C ₃₀ acyl group, a substituted or unsubstituted C ₂ -C ₃₀ alkenyl group , A substituted or unsubstituted C ₂ -C ₃₀ alkynyl group, a substituted or unsubstituted C ₆ -C ₃₀ aryl group, or a substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group, and R ₄ to R ₇ Two or more adjacent ones may combine with each other to form a saturated or unsaturated ring, and two or more adjacent ones of R ₉ to R ₁₂ may combine with each other to form a saturated or unsaturated ring; L ₁ and L ₂ are each independently a single bond, a substituted or unsubstituted C ₁ -C ₃₀ alkylene group, a substituted or unsubstituted C ₆ -C ₃₀ arylene group or a substituted or unsubstituted C ₃ -C ₃₀ hetero Arylene group; Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C ₆ -C ₃₀ aryl group or a substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group; p and q are, independently from each other, an integer from 1 to 5; m and n, independently of each other, are integers from 0 to 4, except that m and n are both zero. The method of claim 1, R ₁ to R ₁₂ are each independently hydrogen, a substituted or unsubstituted C ₁ -C ₁₀ alkyl group, a substituted or unsubstituted C ₂ -C ₁₀ alkenyl group, a substituted or unsubstituted C ₆ -C ₁₂ aryl group Or an imidazopyridine-based compound, which is a C ₃ -C ₁₂ heteroaryl group. The method of claim 1, R ₁ to R ₁₂ are each independently hydrogen, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ haloalkyl group, C ₂ -C ₁₀ alkenyl group, C ₂ -C ₁₀ haloalkenyl group, phenyl group, halophenyl group, Imidazopyridine system characterized by being a C ₁ -C ₁₀ alkylphenyl group, a C ₁ -C ₁₀ alkoxyphenyl group, a naphthyl group, a halonaphthyl group, a C ₁ -C ₁₀ alkylnaphthyl group, or a C ₁ -C ₁₀ alkoxynaphthyl group compound. The method of claim 1, Imidazopyridine-based compound, characterized in that two or more adjacent to each other of the R ₄ to R ₇ or two or more adjacent to each other of the R ₉ to R ₁₂ combine to form a substituted or unsubstituted C ₆ -C ₁₂ aromatic ring . The method of claim 1, The imidazopyridine compound, wherein L ₁ and L ₂ are independently of each other a substituted or unsubstituted C ₆ -C ₁₂ arylene group, or a substituted or unsubstituted C ₃ -C ₁₂ heteroarylene group. The method of claim 1, L ₁ and L ₂ are each independently a phenylene group, a halophenylene group, a C ₁ -C ₁₀ alkylphenylene group, a C ₁ -C ₁₀ alkoxyphenylene group, a naphthylene group, a halonaphthylene group, C ₁ -C ₁₀ An imidazopyridine-based compound, which is an alkyl naphthylene group or a C ₁ -C ₁₀ alkoxy naphthylene group. The method of claim 1, The Ar ₁ and Ar ₂ are independently of each other, a substituted or unsubstituted C ₆ -C ₁₂ aryl group, or a substituted or unsubstituted C ₃ -C ₁₂ heteroaryl group, characterized in that the imidazopyridine-based compound. The method of claim 1, Ar ₁ and Ar ₂ are each independently a phenyl group, a halophenyl group, a C ₁ -C ₁₀ alkylphenyl group, a C ₁ -C ₁₀ alkoxyphenyl group, a naphthyl group, a halonaphthyl group, a C ₁ -C ₁₀ alkylnaphthyl group, C ₁ -C ₁₀ alkoxynaphthyl group, pyridinyl group, halopyridinyl group, C ₁ -C ₁₀ alkylpyridinyl group, C ₁ -C ₁₀ alkoxypyridinyl group, quinolinyl group, haloquinolinyl group, C ₁ -C ₁₀ An alkylquinolinyl group, a C ₁ -C ₁₀ alkoxyquinolinyl group, an isoquinolinyl group, a haloisoquinolinyl group, a C ₁ -C ₁₀ alkylisoquinolinyl group, or a C ₁ -C ₁₀ alkoxyisoquinolinyl group An imidazopyridine compound characterized by the above-mentioned. The method of claim 1, m is 0, n is 1, The imidazopyridine type compound. The method of claim 1, An imidazopyridine-based compound, wherein m and n are 1. The method of claim 1, An imidazopyridine-based compound having the following Chemical Formula 1a, 1b, 1c or 1d: <Formula 1a>

<Formula 1b>

<Formula 1c>

<Formula 1d>

Of the above formula, R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ , R ₁₁ and R ₁₂ are each independently hydrogen, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted C _1- C ₃₀ alkyl group, substituted or unsubstituted C ₁ -C ₃₀ alkoxy group, substituted or unsubstituted C ₁ -C ₃₀ acyl group, substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, substituted or unsubstituted A C ₂ -C ₃₀ alkynyl group, a substituted or unsubstituted C ₆ -C ₃₀ aryl group, or a substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group, two or more adjacent to each other of R ₄ to R ₇ are bonded to each other To form a saturated or unsaturated ring, and two or more adjacent to each other of R ₉ to R ₁₂ may combine with each other to form a saturated or unsaturated ring; Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C ₆ -C ₃₀ aryl group or a substituted or unsubstituted C ₃ -C ₃₀ heteroaryl group. The method of claim 1, Imidazopyridine-based compound, characterized in that any one of compounds 1 to 11 having the structure: <Compound 1> <Compound 2>

<Compound 3> <Compound 4>

<Compound 5>

<Compound 6>

<Compound 7> <Compound 8>

<Compound 9> <Compound 10>

<Compound 11>

A first electrode; Second electrode; And an organic film comprising the compound of any one of claims 1 to 12 between the first electrode and the second electrode. The method of claim 13, The organic light emitting device, characterized in that the organic film is an electron transport layer. The method of claim 12, And at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer and an electron injection layer between the first electrode and the second electrode. The method of claim 13, And the organic layer is an electron transport layer, and further comprises a hole injection layer, a hole transport layer, a light emitting layer, and an electron injection layer between the first electrode and the second electrode.

Images