KR102248540B1 - Hetorocyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides a heterocyclic compound represented by Chemical Formula 1 and an organic light-emitting device including the same.

Description

Heterocyclic compound and organic light emitting device including the same {HETOROCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

The present invention relates to a heterocyclic compound represented by Chemical Formula 1 and an organic light-emitting device including the same.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using an organic material. An organic light-emitting device using the organic light-emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer has a multi-layered structure made of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls to the ground.

Development of a new material for the organic light emitting device as described above is continuously required.

Unexamined Patent Publication No. 10-2011-0027635

The present application is a heterocyclic compound that has excellent hole injection and transport capabilities, and thus lowers the driving voltage of the device, increases luminous efficiency, or improves lifespan characteristics when used in an organic material layer of an organic light-emitting device, particularly a hole injection layer or a hole transport layer, and It is intended to provide an organic light emitting device including the same.

An exemplary embodiment of the present application provides a heterocyclic compound represented by the following formula (1).

[Formula 1]

In Formula 1,

Y is O, S, SiRaRb, PRa or P(=O)Ra,

Ra and Rb are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Alkyl group; Or an aryl group,

L is a direct bond; Or a substituted or unsubstituted arylene group,

Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Hydroxy group; Nitrile group; Nitro group; Ester group; Imide group; Amino group; Carbonyl group; Silyl group; Boron group; Alkyl group; Alkoxy group; Aryloxy group; Alkylthio; Arylthio; Alkyl sulfoxy group; Aryl sulfoxy group; Alkylphosphine group; Arylphosphine group; Phosphine oxide group; Aryl group; And one substituent selected from the group consisting of a heteroaryl group, or a substituent connected with two groups selected from the group,

n is an integer from 1 to 4,

a1 is an integer from 0 to 4,

a2 is an integer from 0 to 6,

a3 is an integer from 0 to 8,

When n and a1 to a3 are each 2 or more, a plurality of L and R1 to R3 are each the same or different.

An exemplary embodiment of the present specification is an organic light-emitting device comprising a first electrode, a second electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the one or more organic material layers It provides an organic light emitting device comprising the above-described heterocyclic compound.

The compound described in the present specification may be used as a material for an organic material layer of an organic light-emitting device. The compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, hole control, or a light emitting material. The compounds described herein can be preferably used as a hole transport or hole injection material.

In some embodiments, the efficiency of the organic light-emitting device including the heterocyclic compound is improved.

In some embodiments, the driving voltage of the organic light-emitting device including the heterocyclic compound is lowered.

In some embodiments, the lifespan characteristics of the organic light-emitting device including the heterocyclic compound are improved.

1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, an organic material layer 3, and a cathode 4.
2 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a hole control layer 7, a light emitting layer 8, an electron transport layer 9, and an electron injection layer 10. And an example of an organic light-emitting device comprising the cathode 4 is shown.

Hereinafter, the present application will be described in more detail.

An exemplary embodiment of the present application provides a heterocyclic compound represented by Chemical Formula 1.

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In this specification,

Means a site bonded to another substituent or a bonding portion.

Examples of the substituents are described below, but are not limited thereto.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Alkyl group; Alkenyl group; Alkynyl group; Halogen group; Hydroxy group; Alkoxy group; Aryloxy group; Pom Ilgi (-CHO); Carboxy group (-COOH); Ester group; Halofoam diary; Alkylcarbonyl group; Arylcarbonyl group; Silyl group; Boron group; Alkylphosphine group; Arylphosphine group; Arylphosphine oxide group; Phosphonate group (-PO ₃ H); Sulfanyl group (-SH); Alkylthio; Arylthio; Alkyl sulfoxy group; Aryl sulfoxy group; Aryl group; Heteroaryl group; Nitrile group (-CN); Imide group; And a nitro group (-NO ₂ ) substituted or unsubstituted with one substituent selected from the group consisting of, or substituted or unsubstituted with a substituent to which two or more groups selected from the group are connected.

For example, in the present specification, the term "substituted or unsubstituted" refers to deuterium; Alkyl group; Alkenyl group; Halogen group; Silyl group; And one substituent selected from the group consisting of an aryl group, or a substituent connected with two groups selected from the group.

In the present specification, an alkyl group refers to a linear or branched saturated hydrocarbon. The number of carbon atoms in the alkyl group is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. The alkyl group may be chain or cyclic.

Specific examples of the chain alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl , Isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

The number of carbon atoms in the cyclic alkyl group (cycloalkyl group) is not particularly limited, but is preferably 3 to 40 carbon atoms. According to an exemplary embodiment, the cycloalkyl group has 3 to 24 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 14 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 8 carbon atoms. Specific examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethyl Cyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the alkenyl group represents a hydrocarbon group having a carbon-carbon double bond, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. Specific examples of the alkenyl group include ethenyl, vinyl, propenyl, allyl, isopropenyl, butenyl, isobutenyl, n-pentenyl and n-hexenyl, but are not limited thereto.

In the present specification, the alkynyl group represents a hydrocarbon group having a carbon-carbon triple bond, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. According to an exemplary embodiment, the alkynyl group has 2 to 20 carbon atoms. Specific examples of the alkynyl group include, but are not limited to, metaynyl, ethynyl, 2-propynyl, 2-butynyl, 1-methyl-2-butynyl, and 2 pentynyl.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the alkoxy group refers to a group in which an alkyl group is bonded to an oxygen atom, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. According to an exemplary embodiment, the alkoxy group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkoxy group has 1 to 10 carbon atoms. Specific examples of the alkoxy group include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, an isobutyloxy group, a sec-butyloxy group, a pentyloxy group, an iso-amyloxy group, and a hexyloxy group.

In the present specification, an aryloxy group means a group in which an aryl group is bonded to an oxygen atom. Specific examples of the aryloxy group include, but are not limited to, phenoxy, 1-naphthyloxy, 3-methylphenoxy, and 4-methoxyphenoxy. Description of the aryl group described below may be applied to the aryl group of the aryloxy group.

In the present specification, the ester group may be substituted with an oxygen of the ester group with a straight chain, branched chain, or cyclic chain alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the haloformyl group is -COX, and X is a halogen group.

In the present specification, an alkylcarbonyl group refers to a carbonyl group (-CO-) to which an alkyl group is bonded.

In the present specification, an arylcarbonyl group refers to a group in which an aryl group is bonded to a carbonyl group (-CO-).

In the present specification, the silyl group may be represented by the formula of -SiRxRyRz, and Rx, Ry, and Rz are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc., but limited thereto. It doesn't work.

In the present specification, the boron group may be represented by the formula of -BRmRn, wherein Rm and Rn are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The boron group specifically includes a dimethyl boron group, a diethyl boron group, a t-butyl ethyl boron group, a diphenyl boron group, a phenyl boron group, and the like, but is not limited thereto.

In the present specification, an alkylphosphine group refers to a group in which an alkyl group is bonded to a phosphine group (-P).

In the present specification, an arylphosphine group refers to a group in which an aryl group is bonded to a phosphine group (-P).

In the present specification, the arylphosphine oxide group refers to a group in which an aryl group is bonded to a _{phosphine oxide group (-PO 2 ).}

In the present specification, an alkylthio group means a group in which an alkyl group is bonded to a thio group (-S).

In the present specification, an arylthio group means a group in which an aryl group is bonded to a thio group (-S).

In the present specification, the sulfoxy group means a group including a -S=O group. Examples of the sulfoxy group include, but are not limited to, a sulfonyl group, a sulfonate group, and a sulfate group.

In the present specification, the alkyl sulfoxy group refers to a group in which the -S=O group is substituted with an alkyl group.

In the present specification, the aryl sulfoxy group refers to a group in which the -S=O group is substituted with an aryl group.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, an alkoxy group; Alkylcarbonyl group; Alkylphosphine group; The description of the above-described alkyl group may be applied to the alkyl group of the alkylthio group and the alkylsulfonyl group.

In the present specification, an aryloxy group; Arylcarbonyl group; Arylphosphine group; Arylphosphine oxide group; Arylthio; And to the aryl group of the aryl sulfoxy group, the description of the aryl group to be described later may be applied.

In the present specification, the above description of the halogen group may be applied to the halogen group of the haloformyl group.

In the present specification, an aryl group means wholly or partially unsaturated substituted or unsubstituted monocyclic or polycyclic. The number of carbon atoms is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 40 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. Examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, and a quarterphenyl group. The polycyclic aryl group is a naphthyl group, anthracenyl group, phenanthrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, phenalenyl group, pyrenyl group, tetracenyl group, chrysenyl group, pentacenyl group , A fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzofluorenyl group, and a spirofluorenyl group, but are not limited thereto.

In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

,

,

,

,

,

,

및

등이 있으나, 이에 한정되지 않는다.The substituted fluorenyl group is

,

,

,

,

,

,

And

And the like, but are not limited thereto.

In the present specification, the heteroaryl group is a cyclic group containing at least one of N, O, and S as a heteroatom, and the number of carbons is not particularly limited, but is preferably 2 to 40 carbon atoms. According to an exemplary embodiment, the number of carbon atoms of the heteroaryl group is 2 to 30. According to another exemplary embodiment, the heteroaryl group has 2 to 20 carbon atoms. Examples of the heteroaryl group include thiophenyl group, furanyl group, pyrrolyl group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridinyl group, bipyridinyl group, pyrimidinyl group, Diazinyl group, triazinyl group, triazolyl group, acridinyl group, carbonyl group, acenaphthoquinoxalinyl group, indenoquinazolinyl group, indenoisoquinolinyl group, indenoquinolinyl group, pyridoindolyl group, Pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinolinyl group, indole Ryl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl group, benzofuranyl group, dibenzofuranyl group, phenanthrolinyl group ( phenanthrolinyl), thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, phenoxazinyl group, and phenothiazinyl group, but are not limited thereto. The heteroaryl group includes an aliphatic heteroaryl group and an aromatic heteroaryl group.

를 의미한다.In the present specification, the term'core structure of Formula 1'

Means.

In the exemplary embodiment of the present specification, Y is O.

In the exemplary embodiment of the present specification, L is a direct bond; Or a substituted or unsubstituted C 6 to C 25 arylene group.

In the exemplary embodiment of the present specification, L is a direct bond; Or a substituted or unsubstituted C6-C18 arylene group.

In the exemplary embodiment of the present specification, L is a direct bond; Or a substituted or unsubstituted C6-C14 arylene group.

In the exemplary embodiment of the present specification, L is a direct bond; Phenylene group; Biphenylene group; Naphthalenylene group; Phenanthrenylene group; Triphenylenylene group; Or an anthracenylene group.

In the exemplary embodiment of the present specification, L is a direct bond; Phenylene group; Biphenylene group; Naphthalenylene group; Or a phenanthrenylene group.

In the exemplary embodiment of the present specification, L is a direct bond; Or any one selected from the following structures.

In the above structures, the two dotted lines mean a portion at which L is bonded to the core structure of Formula 1 and N, respectively.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group, an aryl group, and a heteroaryl group; Or a heteroaryl group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group, an aryl group, and a heteroaryl group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently one or more substituents selected from the group consisting of a C1-C10 alkyl group, a C6-C30 aryl group, and a C2-C30 heteroaryl group. C6-C36 aryl group unsubstituted or substituted with; Or a C2-C30 heteroaryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a C1-C10 alkyl group, a C6-C30 aryl group, and a C2-C30 heteroaryl group.

In the present specification, U-V means U to V, and may mean U or more and V or less.

In the present specification, C1 means 1 carbon atom, and C10 means 10 carbon atoms. Other expressions can also be interpreted as above.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently one or more substituents selected from the group consisting of a C1-C8 alkyl group, a C6-C24 aryl group, and a C2-C24 heteroaryl group. C6-C30 aryl group unsubstituted or substituted with; Or a C2-C24 heteroaryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a C1-C8 alkyl group, a C6-C24 aryl group, and a C2-C24 heteroaryl group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently one or more substituents selected from the group consisting of a C1-C5 alkyl group, a C6-C18 aryl group, and a C2-C18 heteroaryl group. C6-C25 aryl group unsubstituted or substituted with; Or a C2-C16 heteroaryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a C1-C5 alkyl group, a C6-C18 aryl group, and a C2-C18 heteroaryl group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently substituted or provided with one or more substituents selected from the group consisting of an alkyl group, an aryl group, and a heteroaryl group including N, O or S. A cyclic aryl group; Or a heteroaryl group including N, O or S unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group, an aryl group, and a heteroaryl group including N, O or S.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently substituted with one or more substituents selected from the group consisting of an alkyl group, a 1-6 membered aryl group, and a 1-3 membered heteroaryl group. Or an unsubstituted 1-6 membered aryl group; Or a 1-3 membered heteroaryl group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group, a 1-6 membered aryl group, and a 1-3 membered heteroaryl group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophenyl group; Or a substituted or unsubstituted carbazolyl group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently at least one substituent selected from the group consisting of a naphthyl group, a phenanthrenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a carbazolyl group. A phenyl group unsubstituted or substituted with; A biphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a phenanthrenyl group, a carbazolyl group, and a naphthyl group; Terphenyl group; A fluorenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a methyl group and a phenyl group; Naphthyl group; Dibenzofuranyl group; Dibenzothiophenyl group; Or a carbazolyl group.

In the exemplary embodiment of the present specification, R1 is hydrogen.

In the exemplary embodiment of the present specification, R2 is hydrogen.

In the exemplary embodiment of the present specification, R3 is hydrogen.

In the exemplary embodiment of the present specification, a1 is 0.

In the exemplary embodiment of the present specification, a2 is 0.

In the exemplary embodiment of the present specification, a3 is 0.

In the exemplary embodiment of the present specification, the meaning of a1 being 0 means that all hydrogens are located at substitution positions where R can be substituted.

In the exemplary embodiment of the present specification, n is 1.

In the exemplary embodiment of the present specification, n is 2.

In the exemplary embodiment of the present specification, the heterocyclic compound represented by Formula 1 is any one selected from the following heterocyclic compounds.

In the compound of Formula 1 according to the present specification, a compound substituted with Cl as shown in Compounds A to D below is synthesized as in the synthesis method of General Formula 1 below, and then a substituent group containing an amine group in Compounds A to D is the following General Formula 2 It can be synthesized by a substitution method similar to the synthesis method of The following general formulas 1 and 2 are an example of a method of forming the compound of Chemical Formula 1, and the synthesis method of Chemical Formula 1 is not limited to the following general formulas 1 and 2, and may be performed by methods known in the art. . In addition, some synthetic steps can use other known synthetic methods.

[General Formula 1]

[General Formula 2]

대신

등을 사용한다면, 상기 일반식 1 및 2의 합성 방법을 이용하여 상기 화학식 1의 기타 화합물 또한 형성할 수 있다.In the general formula 1, the initial reactant

instead

If the like is used, other compounds of Formula 1 may also be formed by using the synthesis method of Formulas 1 and 2.

In General Formula 2, the definitions of L1, Ar1, and Ar2 are the same as those defined in Chemical Formula 1.

The present specification provides an organic light-emitting device including the compound represented by Chemical Formula 1.

An exemplary embodiment of the present specification is an organic light-emitting device comprising a first electrode, a second electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein the heterocyclic compound of Formula 1 is It provides an organic light-emitting device that is included in one or more of the one or more organic material layers.

An exemplary embodiment of the present specification is an organic light-emitting device comprising an anode, a cathode, and an emission layer provided between the anode and the cathode, wherein the heterocyclic compound of Formula 1 is one or more layers provided between the anode and the emission layer. It provides an organic light-emitting device that is included in one or more of the organic material layers.

In the exemplary embodiment of the present specification, at least one of a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting holes, and a hole control layer may be provided between the anode and the emission layer.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention is an organic material layer, which is a hole injection layer, a hole transport layer, a layer that simultaneously transports and injects holes, a hole control layer, a light-emitting layer, an electron control layer, an electron transport layer, an electron injection layer, and an electron transport and injection at the same time. It may have a structure including a layer or the like.

In the exemplary embodiment of the present specification, the heterocyclic compound is included in the emission layer.

In the exemplary embodiment of the present specification, the heterocyclic compound is included in at least one of a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting holes, and a hole control layer.

In the exemplary embodiment of the present specification, the heterocyclic compound is included in at least one of an electron injection layer, an electron transport layer, a layer that simultaneously injects and transports electrons, and an electron control layer.

In the exemplary embodiment of the present specification, the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In the exemplary embodiment of the present specification, the organic light-emitting device may be an inverted type organic light-emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

In the exemplary embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

In another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

The structure of the organic light-emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 and 2.

The organic light emitting device according to an exemplary embodiment of the present invention may include a substrate 1, an anode 2, an organic material layer 3, and a cathode 4, as shown in FIG. 1. In an exemplary embodiment, the compound of Formula 1 is included in the organic material layer (3).

The organic light emitting device according to an exemplary embodiment of the present invention includes a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a hole control layer 7, and a light emitting layer, as shown in FIG. (8), the electron transport layer 9, the electron injection layer 10 and may be made of a cathode (4). In one embodiment, the compound of Formula 1 is included in the light emitting layer (8). In another embodiment, the compound of Formula 1 is included in any one of the hole transport layer 5, the hole transport layer 6, and the hole control layer 7. In another exemplary embodiment, the compound of Formula 1 is included in the electron transport layer 9 or the electron injection layer 10.

However, the structure of the organic light-emitting device according to the exemplary embodiment of the present specification is not limited to FIGS. 1 and 2 and may be any one of the following structures.

(1) Anode/Hole Transport Layer/Light-Emitting Layer/Anode

(2) Anode/Hole Injection Layer/Hole Transport Layer/Light-Emitting Layer/Anode

(3) Anode/Hole Injection Layer/Hole Buffer Layer/Hole Transport Layer/Light-Emitting Layer/Anode

(4) Anode/Hole Transport Layer/Light-Emitting Layer/Electron Transport Layer/Anode

(5) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode

(7) Anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode

(8) Anode/hole transport layer/hole control layer/light-emitting layer/electron transport layer/cathode

(9) Anode/hole transport layer/hole control layer/light emitting layer/electron transport layer/electron injection layer/cathode

(10) Anode/hole injection layer/hole transport layer/hole control layer/light emitting layer/electron transport layer/cathode

(11) Anode/Hole injection layer/Hole transport layer/Hole control layer/Light-emitting layer/Electron transport layer/Electron injection layer/Anode

(12) Anode/hole transport layer/light emitting layer/electron control layer/electron transport layer/cathode

(13) Anode/Hole Transport Layer/Light-Emitting Layer/Electron Control Layer/Electron Transport Layer/Electron Injection Layer/Anode

(14) Anode/hole injection layer/hole transport layer/light emitting layer/electron control layer/electron transport layer/cathode

(15) Anode/hole injection layer/hole transport layer/light-emitting layer/electron control layer/electron transport layer/electron injection layer/cathode

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, the organic light emitting device of the present specification may be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition method (PVD, physical vapor deposition) such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate. It can be manufactured by forming an anode, forming an organic material layer including a hole injection layer, a hole transport layer, an emission layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.

In addition, the compound of Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

In addition to such a method, an organic light-emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and 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;} Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multilayered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection layer is a layer for injecting holes received from an electrode into a light emitting layer or an adjacent layer provided toward the light emitting layer. The hole injection material has the ability to transport holes and thus has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and transfer of excitons generated in the light emitting layer to the electron injection layer or the electron injection material. It is preferable to use a compound that prevents and is excellent in thin film formation ability. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene. There are a series of organic substances, anthraquinone, and polyaniline and a polythiophene series of conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer. As the hole transport material, a material capable of transporting holes from an anode or a hole injection layer to the light emitting layer and having high mobility for holes is suitable. Specific examples of the hole transport material include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion.

The hole control layer is a layer that prevents electrons from flowing into the light emitting layer to the anode and controls the flow of holes flowing into the light emitting layer to control the performance of the entire device. The hole control material is preferably a compound having the ability to prevent the inflow of electrons from the light-emitting layer to the anode and to control the flow of holes injected into the light-emitting layer or the light-emitting material. In an exemplary embodiment, an arylamine-based organic material may be used as the electron blocking layer, but is not limited thereto.

As the light-emitting material, a material capable of emitting light in a visible light region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzothiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The emission layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladders. Type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material for the light emitting layer include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. As the aromatic amine derivative, as a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, pyrene, anthracene, chrysene, periflanthene and the like having an arylamine group may be used. As the styrylamine compound, a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine may be used. Examples of the styrylamine compound include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. As the metal complex, an iridium complex, a platinum complex, or the like may be used, but is not limited thereto.

The electron control layer is a layer that blocks the inflow of holes from the emission layer to the cathode and controls the electrons flowing into the emission layer to control the performance of the entire device. As the electron controlling material, a compound having the ability to prevent the inflow of holes from the light emitting layer to the cathode and to control electrons injected into the light emitting layer or the light emitting material is preferable. As the electron controlling material, a suitable material may be used according to the configuration of the organic material layer used in the device. The electron control layer is located between the light emitting layer and the cathode, and is preferably provided in direct contact with the light emitting layer.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high mobility for electrons is suitable. Examples of the electron transport material include an Al complex of 8-hydroxyquinoline; Complexes containing Alq _3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer can be used with any desired negative electrode material as used according to the prior art. In an exemplary embodiment, as the negative electrode material, a material having a low work function; And an aluminum layer or a silver layer. Examples of the material having the low work function include cesium, barium, calcium, ytterbium, and samarium. After forming a layer with the material, an aluminum layer or a silver layer may be formed on the layer.

The electron injection layer is a layer for injecting electrons received from an electrode into the light emitting layer. The electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and transfer of excitons generated in the light emitting layer to the hole injection layer or the hole injection material In addition, it is preferable to use a compound having excellent ability to form a thin film. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.

The organic light-emitting device according to the present specification may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.

Hereinafter, for a detailed understanding of the present invention, a method and characteristics of the heterocyclic compound of the present invention and an organic light-emitting device including the same will be described.

Manufacturing example One

After completely dissolving Compound B (5.25g, 11.51mmol) and Compound a1 (5.84g, 13.23mmol) in 240 mL of tetrahydrofuran in a nitrogen atmosphere in a 500 mL round-bottom flask, 2M aqueous potassium carbonate solution (120 mL) was added, and tetrakis ( Triphenylphosphine) palladium (0.4g, 0.35mmol) was added, followed by heating and stirring for 12 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 180 mL of ethyl acetate to prepare compound 1 (6.86 g, yield 73%).

MS[M+H] ⁺ = 817

Manufacturing example 2

Compound C (5.25g, 11.51mmol) and compound a2 (6.36g, 13.23mmol) were completely dissolved in 220 mL of tetrahydrofuran in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (110 mL) was added. (Triphenylphosphine) palladium (0.4g, 0.35mmol) was added, followed by heating and stirring for 12 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 180 mL of ethyl acetate to prepare compound 2 (5.22 g, yield 53%).

MS[M+H] ⁺ = 857

Manufacturing example 3

Compound A (5.77 g, 12.67 mmol) and compound a3 (5.52 g, 14.57 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (120 mL) was added, and tetrakis ( Triphenylphosphine) palladium (0.44g, 0.38mmol) was added, followed by heating and stirring for 12 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 mL of acetone to prepare compound 3 (4.59 g, yield 48%).

MS[M+H] ⁺ = 755

Manufacturing example 4

Compound D (5.77 g, 12.67 mmol) and compound a4 (6.49 g, 14.57 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (120 mL) was added, and tetrakis- (Triphenylphosphine) palladium (0.44g, 0.38mmol) was added, followed by heating and stirring for 12 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 220 mL of ethyl acetate to prepare compound 4 (6.14 g, 59%).

MS[M+H] ⁺ = 821

Manufacturing example 5

Compound B (5.25g, 11.51mmol) and compound a5 (4.06g, 12.66mmol) were completely dissolved in 220 mL of xylene in a 500 mL round bottom flask in a nitrogen atmosphere, NaOtBu (1.44g, 14.96mmol) was added, and bis[ (Tri-tertiary-butyl) phosphine] palladium (0.12 g, 0.23 mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to prepare compound 5 (6.31 g, yield 74%).

MS[M+H] ⁺ = 741

Manufacturing example 6

After completely dissolving Compound B (5.25g, 11.51mmol) and Compound a6 (4.57g, 12.66mmol) in 220 mL of xylene in a nitrogen atmosphere in a 500 mL round bottom flask, NaOtBu (1.44g, 14.96mmol) was added, and bis[((() Tri-tertiary-butyl)phosphine]palladium (0.17g, 0.34mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with ethyl acetate 260 mL to prepare compound 6 (5.75 g, yield 64%).

MS[M+H] ⁺ = 781

Manufacturing example 7

After completely dissolving compound C (5.25g, 11.51mmol) and compound a7 (4.37g, 12.66mmol) in 220 mL of xylene in a nitrogen atmosphere, NaOtBu (1.44g, 14.96mmol) was added, and bis[(((()) Tri-tertiary-butyl) phosphine] palladium (0.12g, 0.23mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 220 mL of ethyl acetate to prepare compound 7 (5.1 g, yield 58%).

MS[M+H] ⁺ = 765

Manufacturing example 8

Compound A (5.25g, 11.51mmol) and compound a8 (5.19g, 12.66mmol) were completely dissolved in 220 mL of xylene in a nitrogen atmosphere, and NaOtBu (1.44g, 14.96mmol) was added, followed by bis[ (Tri-tertiary-butyl) phosphine] palladium (0.12g, 0.23mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with ethyl acetate 260 mL to prepare compound 8 (6.4 g, yield 67%).

MS[M+H] ⁺ = 830

Manufacturing example 9

Compound B (5.25g, 11.51mmol) and compound a9 (6.84g, 13.23mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (120 mL) was added, and tetrakis ( Triphenylphosphine) palladium (0.4g, 0.35mmol) was added, followed by heating and stirring for 12 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 180 mL of ethyl acetate to prepare compound 9 (7.5 g, yield 73%).

MS[M+H] ⁺ = 893

Manufacturing example 10

Compound B2 (5.25 g, 11.51 mmol) and compound a10 (4.06 g, 12.66 mmol) were completely dissolved in 220 mL of xylene in a 500 mL round bottom flask in a nitrogen atmosphere, and NaOtBu (1.44 g, 14.96 mmol) was added, and bis[((() Tri-tertiary-butyl) phosphine] palladium (0.12g, 0.23mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to prepare compound 10 (6.27 g, yield 72%).

MS[M+H] ⁺ = 757

Example 1-1

A glass substrate coated with a thin film of ITO (indium tin oxide) having a thickness of 1,000Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

A hole injection layer was formed by thermally vacuum evaporating a compound of the following compound HI1 and the following compound HI2 to a thickness of 100 Å in a ratio of 98:2 (molar ratio) on the prepared ITO transparent electrode, which is an anode. A hole transport layer (1150Å) was formed by vacuum depositing a compound represented by the following formula HT1 on the hole injection layer. Subsequently, the compound of Preparation Example 1 was vacuum-deposited on the hole transport layer with a film thickness of 50 Å to form a hole control layer. Subsequently, a compound represented by the following formula BH and a compound represented by the following formula BD having a film thickness of 200 Å on the hole control layer were vacuum-deposited at a weight ratio of 25:1 to form a light emitting layer. An electron control layer was formed by vacuum depositing a compound represented by the following formula HB1 with a film thickness of 50Å on the emission layer. Subsequently, a compound represented by the following formula ET1 and a compound represented by the following formula LiQ were vacuum-deposited at a weight ratio of 1:1 on the electron control layer to form an electron injection and transport layer with a thickness of 310 Å. Lithium fluoride (LiF) in a thickness of 12 Å and aluminum in a thickness of 1,000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.

In the above process, the deposition rate of the organic material was maintained from 0.4 Å/sec to 0.7 Å/sec, the deposition rate of lithium fluoride of the negative electrode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum degree during deposition was 2×10. ^{- 7} torr to 5ⅹ10 ^- holding a ⁶ torr, was produced in the organic light emitting device.

Example 1-2 to Example 1-10

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1 of Preparation Example 1.

Comparative example 1-1 to 1-3

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1 of Preparation Example 1. The compounds of EB2, EB3, and EB4 used in Table 1 are as follows.

When a current was applied to the organic light emitting device prepared in the above Examples and Comparative Examples, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T95 refers to the time it takes for the luminance to decrease from the initial luminance (1600 nit) to 95%.

compound
(Hole control layer) Voltage
(V@10mA
/cm ² ) efficiency
(cd/A@10mA
/cm ² ) Color coordinates
(x,y) T95
(hr) Example 1-1 Compound 1 4.51 6.21 (0.141, 0.046) 285 Example 1-2 Compound 2 4.52 6.25 (0.142, 0.045) 290 Example 1-3 Compound 3 4.53 6.26 (0.143, 0.044) 295 Example 1-4 Compound 4 4.54 6.27 (0.139, 0.047) 285 Example 1-5 Compound 5 4.56 6.23 (0.142, 0.044) 285 Example 1-6 Compound 6 4.47 6.49 (0.139, 0.042) 270 Example 1-7 Compound 7 4.48 6.33 (0.141, 0.045) 285 Example 1-8 Compound 8 4.39 6.42 (0.143, 0.046) 265 Example 1-9 Compound 9 4.52 6.25 (0.138, 0.045) 290 Example 1-10 Compound 10 4.41 6.47 (0.140, 0.043) 265 Comparative Example 1-1 EB2 7.24 3.18 (0.152, 0.047) 40 Comparative Example 1-2 EB3 5.06 5.05 (0.146, 0.045) 155 Comparative Example 1-3 EB4 5.60 5.69 (0.145, 0.046) 175

As shown in Table 1, the organic light-emitting device using the compound of the present invention as a hole control layer exhibited excellent characteristics in terms of efficiency, driving voltage, and stability of the organic light-emitting device.

가 결합된 코어에 아민기가 치환된 EB3의 물질을 사용하여 제조된 비교예 1-2, 및 (c) -L-Ar1이 코어의 다른 벤젠고리에 치환된 EB4의 물질을 사용하여 제조된 비교예 1-3의 유기 발광 소자보다 저전압, 고효율 및 장수명의 특성을 나타내었다.The devices of Examples 1-1 to 1-10 are (a) 10',10'-dimethyl-10H,10'H-9,9'-spirobi[anthracene]-10-one EB2 with an amine group connected to the core Comparative Example 1-1 prepared using the material of (b) instead of -O- of the core of the present application

Comparative Example 1-2 prepared using a material of EB3 in which an amine group is substituted on the core to which is bonded, and (c) a comparative example prepared using a material of EB4 in which -L-Ar1 is substituted with another benzene ring of the core Compared to the organic light-emitting devices of 1-3, it exhibited the characteristics of low voltage, high efficiency, and long life.

As shown in the results of Table 1, it was confirmed that the compound according to the present invention has excellent electron blocking ability and thus can be applied to an organic light-emitting device.

Example 2-1 to Example 2-10

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound of EB1 was used instead of the compound 1 of Preparation Example 1, and the compound of Table 1 was used instead of HT1.

Comparative example 2-1 to 2-3

An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that the compound shown in Table 1 was used instead of Compound 1 of Preparation Example 1. The compounds of HT2, HT3, and HT4 used in Table 1 are as follows.

When a current was applied to the organic light emitting device manufactured in the above Examples and Comparative Examples, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 2 below. T95 refers to the time it takes for the luminance to decrease from the initial luminance (1600 nit) to 95%.

compound
(Hole transport layer) Voltage
(V@10mA
/cm ² ) efficiency
(cd/A@10mA
/cm ² ) Color coordinates
(x,y) T95
(hr) Example 2-1 Compound 1 4.21 6.30 (0.141, 0.045) 265 Example 2-2 Compound 2 4.20 6.33 (0.142, 0.047) 275 Example 2-3 Compound 3 4.25 6.31 (0.143, 0.047) 270 Example 2-4 Compound 4 4.26 6.39 (0.144, 0.045) 265 Example 2-5 Compound 5 4.27 6.35 (0.142, 0.044) 265 Example 2-6 Compound 6 4.27 6.57 (0.142, 0.046) 250 Example 2-7 Compound 7 4.25 6.46 (0.141, 0.043) 265 Example 2-8 Compound 8 4.31 6.54 (0.145, 0.045) 240 Example 2-9 Compound 9 4.30 6.37 (0.141, 0.044) 275 Example 2-10 Compound 10 4.36 6.55 (0.142, 0.043) 245 Comparative Example 2-1 HT2 7.17 3.27 (0.143, 0.046) 150 Comparative Example 2-2 HT3 5.05 5.83 (0.142, 0.045) 140 Comparative Example 2-3 HT4 5.57 5.06 (0.150, 0.049) 50

As shown in Table 2, the organic light-emitting device using the compound of the present invention as a hole transport layer exhibited excellent characteristics in terms of efficiency, driving voltage, and stability of the organic light-emitting device.

가 결합된 코어에 아민기가 치환된 HT3의 물질을 사용하여 제조된 비교예 2-2, 및 (c) -L-Ar1이 코어의 다른 벤젠고리에 치환된 HT4의 물질을 사용하여 제조된 비교예 2-3의 유기 발광 소자보다 저전압, 고효율 및 장수명의 특성을 나타내었다.The devices of Examples 2-1 to 2-10 were (a) 10',10'-dimethyl-10H,10'H-9,9'-spirobi[anthracene]-10-on core with an amine group connected to HT2 Comparative Example 2-1 prepared using the material of, (b) instead of -O- of the core of the present application

Comparative Example 2-2 prepared using a material of HT3 substituted with an amine group on the core to which is bonded, and (c) a comparative example prepared using a material of HT4 in which -L-Ar1 is substituted with another benzene ring of the core It exhibited the characteristics of lower voltage, high efficiency, and longer life than 2-3 organic light emitting devices.

As shown in the results of Table 2, it was confirmed that the compound according to the present invention has excellent hole transport ability and thus can be applied to an organic light-emitting device.

Preferred embodiments of the present invention (hole control layer, hole transport layer) have been described above, but the present invention is not limited thereto, and various modifications can be made within the scope of the claims and the detailed description of the invention. And this also belongs to the scope of the invention.

1: substrate
2: anode
3: organic material layer
4: cathode
5: hole injection layer
6: hole transport layer
7: hole control layer
8: light emitting layer
9: electron transport layer
10: electron injection layer

Claims (12)

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

In Formula 1,
Y is O, or S,
Ra and Rb are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Alkyl group; Or an aryl group,
L is a direct bond; Or a substituted or unsubstituted arylene group,
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Hydroxy group; Nitrile group; Nitro group; Ester group; Imide group; Amino group; Carbonyl group; Silyl group; Boron group; Alkyl group; Alkoxy group; Aryloxy group; Alkylthio; Arylthio; Alkyl sulfoxy group; Aryl sulfoxy group; Alkylphosphine group; Arylphosphine group; Phosphine oxide group; Aryl group; And one substituent selected from the group consisting of a heteroaryl group, or a substituent connected with two groups selected from the group,
n is an integer from 1 to 4,
a1 is an integer from 0 to 4,
a2 is an integer from 0 to 6,
a3 is an integer from 0 to 8,
When n and a1 to a3 are each 2 or more, a plurality of L and R1 to R3 are each the same or different. The method according to claim 1, wherein the formula 1 is a heterocyclic compound represented by any one of the following formulas 2 to 5:
[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5,
The definitions of Y, L, Ar1, Ar2, R1 to R3, a1 to a3, and n are the same as those defined in Formula 1. The method according to claim 1, wherein L is a direct bond; Or a heterocyclic compound that is an arylene group having 6 to 25 carbon atoms. The method according to claim 1, wherein L is a direct bond; Phenylene group; Biphenylene group; Naphthalenylene group; Phenanthrenylene group; Triphenylenylene group; Or a heterocyclic compound that is an anthracenylene group. The method according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group, an aryl group, and a heteroaryl group; Or a heterocyclic compound that is a heteroaryl group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group, an aryl group and a heteroaryl group. The method according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophenyl group; Or a substituted or unsubstituted carbazolyl group that will be a heterocyclic compound. The method according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and each independently substituted or provided with one or more substituents selected from the group consisting of a naphthyl group, a phenanthrenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a carbazolyl group. A cyclic phenyl group; A biphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a phenanthrenyl group, a carbazolyl group, and a naphthyl group; Terphenyl group; A fluorenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a methyl group and a phenyl group; Naphthyl group; Dibenzofuranyl group; Dibenzothiophenyl group; Or a heterocyclic compound that is a carbazolyl group. The heterocyclic compound of claim 1, wherein the heterocyclic compound represented by Formula 1 is any one selected from the following heterocyclic compounds:

. An organic light-emitting device comprising a first electrode, a second electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein the heterocyclic compound according to any one of claims 1 to 8 is 1 An organic light-emitting device that is included in one or more of the organic material layers of a layer or more. The organic light-emitting device of claim 9, wherein the heterocyclic compound is included in the emission layer. The organic light-emitting device of claim 9, wherein the heterocyclic compound is included in at least one of a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting holes, and a hole control layer. The organic light-emitting device of claim 9, wherein the heterocyclic compound is included in at least one of an electron injection layer, an electron transport layer, a layer simultaneously injecting and transporting electrons, and an electron controlling layer.

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