KR102250388B1 - Heterocyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a heterocyclic compound of Formula 1 and an organic light emitting device including the same.

Description

Heterocyclic compound and organic light-emitting device comprising the same TECHNICAL FIELD

The present invention claims the benefit of the filing date of Korean Patent No. 10-2018-0076399 filed with the Korean Intellectual Property Office on July 02, 2018, the entire contents of which are incorporated herein.

The present specification relates to a heterocyclic compound, and an organic light emitting device formed using the heterocyclic compound.

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 is often made of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of 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 such an 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. When it falls back to the ground, it glows.

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

US Patent Application Publication No. 2004-0251816

The present specification provides a heterocyclic compound and an organic light emitting device including the same.

An exemplary embodiment of the present specification provides a heterocyclic compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

However, at least two of Ar2 to Ar4 are a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

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

R1 to R3 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkylamine group, a substituted Or an unsubstituted arylamine group, a substituted or unsubstituted alkyloxy group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted aryl group,

m to o are the same as or different from each other, and each independently an integer of 1 to 4,

When n is 2 or more, R1 is the same as or different from each other,

When m is 2 or more, R2 is the same as or different from each other,

When o is 2 or more, R3 is the same as or different from each other.

In addition, another exemplary embodiment of the present specification is a first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the heterocyclic compound.

The heterocyclic compound according to an exemplary embodiment of the present specification may be used as a material for an organic material layer of an organic light emitting device, and by using it, low voltage and long life characteristics may be obtained in the organic light emitting device.

1 illustrates an organic light-emitting device according to an exemplary embodiment of the present specification.
2 illustrates an organic light-emitting device according to an exemplary embodiment of the present specification.

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

According to an exemplary embodiment of the present specification, a heterocyclic compound represented by Chemical Formula 1 is provided.

In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless otherwise stated.

Examples of the substituent in the present specification are described below, but are not limited thereto.

The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group substituted with one or two or more substituents selected from the group consisting of, or two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents. For example, the "substituent to which two or more substituents are connected" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, and the like.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 30 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are limited thereto. It is not.

In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it has 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a phenalenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but are limited thereto. no.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In the present specification, the heteroaryl group includes one or more atoms other than carbon and one or more heteroatoms, and specifically, the heteroatom may include one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Zolyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, p Nanthrolinyl group (phenanthroline), isoxazolyl group, thiadiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but are not limited thereto.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.

In the present specification, examples of the heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as those of the aforementioned heteroaryl group.

In the present specification, the arylene group is the same as the definition of the aryl group, except that it is divalent.

In the present specification, the heteroarylene group is the same as the definition of the heteroaryl group, except that it is divalent.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of Chemical Formulas 2 to 2 below.

In Formulas 2 to 13, Ar1 to Ar4, R1 to R3, and m to o are as defined in Formula 1.

According to an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently, hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, A substituted or unsubstituted alkylamine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted alkyloxy group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently, hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkene having 1 to 10 carbon atoms. Nyl group, substituted or unsubstituted alkynyl group having 1 to 10 carbon atoms, amine group substituted with an alkyl group having 1 to 10 carbon atoms, amine group substituted with an aryl group having 6 to 20 carbon atoms, substituted or unsubstituted alkyl having 1 to 10 carbon atoms It is an oxy group, a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently, an amine group substituted with hydrogen, deuterium, methyl group, ethyl group, propyl group, butyl group, terbutyl group, phenyl group or naphthyl group , A methoxy group, an ethoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrene group, or an anthracene group.

According to an exemplary embodiment of the present specification, R1 to R3 are hydrogen.

According to an exemplary embodiment of the present specification, L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L is an arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L is a direct bond.

According to an exemplary embodiment of the present specification, L is a phenylene group.

According to an exemplary embodiment of the present specification, L is a naphthalene group.

According to an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently, hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted carbon number 3 to 30 It is a heteroaryl group of.

According to an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently, hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted carbon number 3 to 30 It is a heteroaryl group containing any one or more of N, O, and S.

According to an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently, an aryl group or a heteroaryl group,

The aryl group or heteroaryl group is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amine It is unsubstituted or substituted with one or more substituents selected from the group consisting of a group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently, an aryl group or a heteroaryl group,

The aryl group or heteroaryl group is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms A phosphine oxide group, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, an amine group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted aryl group It is unsubstituted or substituted with one or more substituents selected from the group consisting of a cyclic C3 to C20 heteroaryl group.

According to an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently, an aryl group or a heteroaryl group,

The aryl group or heteroaryl group is hydrogen, deuterium, methyl group, ethyl group, propyl group, isopropyl group, butyl group, terbutyl group, silyl group substituted with methyl group, phosphine oxide group substituted with phenyl group or naphthyl group, methoxy group , An ethoxy group, a propoxy group, a butoxy group, a terbutoxy group, an amine group substituted with a phenyl group or a biphenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracene group, a phenanthrene group, a pyrene group, a triphenylene group, Fluorene group, pyridine group, pyrimidine group, triazine group, pyrrole group, furan group, dibenzofuran group, dibenzothiophene group, benzonaphthofuran group, benzonaphthothiophene, unsubstituted or substituted with a methyl group or a phenyl group It is unsubstituted or substituted with one or more substituents selected from the group consisting of a group, a phenyl group, or a carbazole group unsubstituted or substituted with a naphthyl group.

According to the exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen, deuterium, alkyl group, silyl group, phosphine oxide group, alkoxy group, amine group, or aryl group substituted or unsubstituted Aryl group having 6 to 30 carbon atoms; Or hydrogen, deuterium, alkyl group, silyl group, phosphine oxide group, alkoxy group, amine group, or aryl group substituted or unsubstituted substituted or unsubstituted N, O, and any one or more of N, O, and S having 3 to 30 carbon atoms It is a containing heteroaryl group.

According to an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently, a phenyl group unsubstituted or substituted with deuterium or an aryl group; A biphenyl group unsubstituted or substituted with deuterium or an aryl group; Terphenyl group unsubstituted or substituted with deuterium or aryl group; A naphthyl group unsubstituted or substituted with deuterium or an aryl group; A phenanthrene group unsubstituted or substituted with deuterium or an aryl group; Anthracene group unsubstituted or substituted with deuterium or aryl group; Triphenylene group unsubstituted or substituted with deuterium or aryl group; A dibenzofuran group unsubstituted or substituted with an aryl group; A dibenzothiophene group unsubstituted or substituted with an aryl group; A carbazole group unsubstituted or substituted with an aryl group; A pyridine group unsubstituted or substituted with an aryl group; A pyrimidine group unsubstituted or substituted with an aryl group; Or a triazine group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently, a phenyl group unsubstituted or substituted with a deuterium group, a naphthyl group, a phenanthrene group, or a triphenylene group; Biphenyl group; Terphenyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Phenanthrene group; Triphenylene group; Dibenzofuran group; Dibenzothiophene group; Carbazole; Or a pyridine group.

According to an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently, a phenyl group; Naphthyl group; Biphenyl group; Phenanthrene group; Triphenylene group; Pyren group; Fluoranthene group; Dibenzofuran group; Dibenzothiophene group; Or a carbazole group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, Ar2 to Ar4 are the same as each other.

According to an exemplary embodiment of the present specification, Ar2 to Ar4 are different from each other.

According to an exemplary embodiment of the present specification, Ar2 and Ar3 are the same as each other.

According to an exemplary embodiment of the present specification, Ar2 and Ar3 are different from each other.

According to an exemplary embodiment of the present specification, Ar2 and Ar4 are the same as each other.

According to an exemplary embodiment of the present specification, Ar2 and Ar4 are different from each other.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as each other.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are different from each other.

According to an exemplary embodiment of the present specification, Ar2 to Ar4 are the same as or different from each other, and each independently, a phenyl group; Naphthyl group; Biphenyl group; Phenanthrene group; Triphenylene group; Pyren group; Fluoranthene group; Dibenzofuran group; Dibenzothiophene group; Or a carbazole group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and each independently, a phenyl group; Naphthyl group; Biphenyl group; Phenanthrene group; Triphenylene group; Pyren group; Fluoranthene group; Dibenzofuran group; Dibenzothiophene group; Or a carbazole group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, Ar2 and Ar4 are the same as or different from each other, and each independently, a phenyl group; Naphthyl group; Biphenyl group; Phenanthrene group; Triphenylene group; Pyren group; Fluoranthene group; Dibenzofuran group; Dibenzothiophene group; Or a carbazole group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently, a phenyl group; Naphthyl group; Biphenyl group; Phenanthrene group; Triphenylene group; Pyren group; Fluoranthene group; Dibenzofuran group; Dibenzothiophene group; Or a carbazole group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, Ar1 is the same as or different from each other, and each independently, a phenyl group unsubstituted or substituted with a deuterium group, a naphthyl group, a phenanthrene group, or a triphenylene group; A naphthyl group unsubstituted or substituted with a phenyl group; Biphenyl group; Terphenyl group; Phenanthrene group; Triphenylene group; Dibenzofuran group; Or a dibenzothiophene group.

According to the exemplary embodiment of the present specification, Ar2 to Ar4 may be the same as or different from each other, and each independently, may be any one of the following substituents.

According to an exemplary embodiment of the present specification, Ar1 may be any one of the following substituents.

According to another exemplary embodiment of the present specification, the heterocyclic compound of Formula 1 may be represented by the following structural formulas.

In addition, the organic light emitting device according to the present invention includes a first electrode; A second electrode provided opposite to the first electrode; And one or two or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the heterocyclic compound of Formula 1.

The organic light-emitting device of the present invention may be manufactured by a conventional method and material of an organic light-emitting device, except that one or more organic material layers are formed using the above-described heterocyclic compound.

The organic material layer of the organic light emitting device of the present invention 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 may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic material layers. In addition, the organic material layer may include at least one of an electron transport layer, an electron injection layer, and a layer that simultaneously transports electrons and injects electrons, and at least one of the layers may include the heterocyclic compound.

For example, the structure of the organic light-emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.

1 illustrates a structure of an organic light emitting diode in which a first electrode 2, a light emitting layer 3, and a second electrode 4 are sequentially stacked on a substrate 1.

2, a first electrode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron injection and transport layer 7 and a second electrode 4 are sequentially formed on the substrate 1 The structure of the stacked organic light emitting device is illustrated.

In an exemplary embodiment of the present invention, the organic material layer including the heterocyclic compound of Formula 1 may include an emission layer, and the heterocyclic compound of Formula 1 may be included in the emission layer.

In an exemplary embodiment of the present invention, the organic material layer including the heterocyclic compound of Formula 1 includes an emission layer, and the emission layer includes a host and a dopant in a ratio of 99:1 to 80:20.

In an exemplary embodiment of the present invention, the organic material layer including the heterocyclic compound of Formula 1 includes an emission layer, and the host of the emission layer is used in an amount of 80 to 99% by weight based on the sum of the host and the dopant.

In an exemplary embodiment of the present invention, the organic material layer including the heterocyclic compound of Formula 1 includes an emission layer, and includes the heterocyclic compound of Formula 1 as a blue host of the emission layer.

In an exemplary embodiment of the present invention, the emission layer includes the compound of Formula A as a dopant.

[Formula A]

In Formula A,

X is B, P(=O) or P(=S),

A1 to A3 are the same as or different from each other, and each independently a monocyclic or polycyclic ring,

G1 to G3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Alkyl group; Aryl group; Heteroaryl group; Alkylamine group; A substituted or unsubstituted arylamine group; Or a heteroarylamine group, or may form a ring through Y3 by bonding with an adjacent group,

Y3 is a direct bond; O; C(Rm)(Rn); N(Rp); Or a substituted or unsubstituted silyl group,

Y1 and Y2 are the same as or different from each other, and each independently O or N(Rp),

Rm, Rn and Rp are the same as or different from each other, and each independently hydrogen, deuterium, an alkyl group, or a substituted or unsubstituted aryl group, or combine with an adjacent group to form a substituted or unsubstituted ring,

b1 to b3 are each an integer greater than or equal to 0,

When b1 to b3 are each 2 or more, the structures in the two or more parentheses are the same as or different from each other.

In an exemplary embodiment of the present invention, the emission layer includes any one of the following compounds as a dopant.

In an exemplary embodiment of the present invention, the organic material layer containing the heterocyclic compound of Formula 1 includes a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, or the electron blocking layer is the heterocyclic layer. It may contain a compound.

In an exemplary embodiment of the present invention, the organic material layer including the heterocyclic compound of Formula 1 includes an electron injection layer, an electron transport layer, or a hole blocking layer, and the electron injection layer, the electron transport layer, or the hole blocking layer is the heterocycle. It may contain a compound.

For example, the organic light-emitting device according to the present invention uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and uses a metal or conductive metal oxide or alloy thereof on a substrate. A material that can be used as a cathode after forming an anode by depositing a hole injection layer, a hole transport layer, a light emitting layer, an organic material layer including an electron transport layer, and an organic material layer including the heterocyclic compound of Formula 1 thereon. Can be prepared by evaporating. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

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); A combination of a metal and an oxide such as ZnO:Al or SnO _{2 :Sb;} Poly(3-methyl compounds), poly[3,4-(ethylene-1,2-dioxy) compounds] (PEDT), conductive polymers such as polypyrrole and polyaniline, 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 material is a material that can well inject holes from the anode at a low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Of organic matter, anthraquinone, and conductive polymers of a series of polyaniline and polycompounds, but are not limited thereto.

The hole transport material is a material capable of transporting holes from an anode or a hole injection layer and transferring them to the emission layer, and a material having high mobility for holes is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are 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-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

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.

The organic light-emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one of the organic material layers is formed using the heterocyclic compound.

The present specification also provides a method of manufacturing an organic light-emitting device formed by using the heterocyclic compound.

Dopant materials include aromatic heterocyclic compounds, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic heterocyclic compound is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periflanthene and the like having an arylamino group, and the styrylamine compound is substituted or unsubstituted. A compound in which at least one arylvinyl group is substituted on the cyclic arylamine, and one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, and styryltetraamine, but are not limited thereto. In addition, examples of the metal complex include, but are not limited to, an iridium complex and a platinum complex.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer.As an electron transport material, a material capable of receiving electrons from the cathode and transferring them to the emission layer, and a material having high mobility for electrons is suitable. Do. Specific examples include 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 cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case an aluminum layer or a silver layer follows.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, has an excellent electron injection effect on the light emitting layer or light emitting material, and injects holes of excitons generated in the light emitting layer. A compound that prevents migration to the layer and is excellent in thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic 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 8-hydroxyquinolinato lithium, 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 hole blocking layer is a layer that prevents holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but are not limited thereto.

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.

According to an exemplary embodiment of the present specification, the heterocyclic compound of Formula 1 may be prepared according to the following reaction scheme, but is not limited thereto. In the following reaction scheme, various types of intermediates can be synthesized according to the type and number of substituents appropriately selecting a known starting material by a person skilled in the art. As for the reaction type and reaction conditions, those known in the art may be used.

Synthesis Example 1. Synthesis of Compound 1-1

[1,1':2',1''-terphenyl]-3'-ol (100 g,406 mmol) and diisopropylamine (4.2 g, 41 mmol) were added to a round bottom flask and chloroform was added to 1000 ml. Melted. After lowering the temperature to 0°C, n-bromosuccinimide (73.7 g, 414 mmol) was divided into 10 times and slowly added. After the addition was completed, the mixture was stirred at 0°C for 1 hour, and then the temperature was raised to room temperature and stirred for 1 hour. Dilute sulfuric acid was added, stirred for 30 minutes, and the organic layer was separated using a separatory funnel, and washed several times with water. Magnesium sulfate was added to the organic layer to remove water, and then filtered. The filtrate was collected, distilled under reduced pressure to remove the solvent, and purified using column chromatography to obtain 4'-bromo-[1,1':2',1''-terphenyl]-3-ol. (63g, 194 mmol)

4'-bromo-[1,1':2',1''-terphenyl]-3'-ol (63 g, 194 mmol) and (2-fluorophenyl) boronic acid (32.5 g, 232 mmol) ) Was placed in a round bottom flask and dissolved in 1000 ml of tetrahydrofuran (THF). Potassium carbonate (53.5 g, 387 mmol) was dissolved in 300 ml of distilled water and added, and bis(tri-ter-butylphosphine)palladium(0) (198 mg, 0.39 mmol) was added. After refluxing for 2 hours and cooling, the organic layer was separated. After distillation under reduced pressure to remove tetrahydrofuran (THF), it was dissolved in chloroform, placed in a separatory funnel, and washed several times with water. Magnesium sulfate was added to the organic layer to remove water, and then filtered. The filtrate was distilled under reduced pressure to remove the solvent. The obtained 4'-(2-fluorophenyl)-[1,1':2',1''-terphenyl]-3'-ol (51 g, 149 mmol) was directly used in the next reaction.

Put 4'-(2-fluorophenyl)-[1,1':2',1''-terphenyl]-3'-ol (51 g, 149 mmol) in a round bottom flask and add 400 ml of chloroform. After melting, the temperature was lowered to 0°C. After dissolving n-bromosuccinimide (29g, 165 mmol) in 100 ml of dimethylformamide, it was slowly added. After the addition was completed, the temperature was gradually raised to room temperature and then stirred for 1 hour. After the reaction solution and distilled water were added to a separatory funnel and extracted several times, only the organic layer was separated, and magnesium sulfate was added to remove water. Chloroform was removed by distillation under reduced pressure and purified by column chromatography. (47 g, 115 mmol)

6'-bromo-4'-(2-fluorophenyl)-[1,1':2',1''-terphenyl]-3'-ol (47 g, 115 mmol), potassium carbonate (63.3 g , 458 mmol) and 400 ml of dimethylacetamide were added to a round bottom flask and stirred under reflux for 3 hours. After cooling, the reaction solution is poured into 1.5 L of distilled water. When a solid precipitated, it was filtered. After dissolving in 750 ml of chloroform, it was washed several times with distilled water using a separatory funnel. Magnesium sulfate was added to the organic layer to remove water and filtered. It was purified using column chromatography. (43 g, 108 mmol)

2-bromo-3,4-diphenyldibenzo[b,d]furan (43 g, 108 mmol), (10-phenylanthracene-9-yl) boronic acid (32.1 g, 108 mmol) in a round bottom flask And dissolved in 500 ml of tetrahydrofuran (THF). Potassium carbonate (29.8 g, 215 mmol) was dissolved in 100 ml of distilled water and added, and tetrakis (triphenylphosphine) palladium (0) (3.73 g, 3.23 mmol) was added. The mixture was stirred at reflux for 18 hours and then cooled. The resulting solid was filtered and recrystallized with toluene to obtain compound 1-1 (37g, 65 mmol).

Synthesis Examples 2 to 4. Synthesis of Compounds 1-14, 1-68, and 1-96

In Synthesis Example 1, instead of (10-phenylanthracene-9-yl)boronic acid, (10-(naphthalen-1-yl)anthracene-9-yl)boronic acid, (10-(dibenzo[b,d]furan- 1-yl) anthracene-9-yl) boronic acid and (4-(10-phenylanthracene-9-yl) phenyl) boronic acid were used in the same manner as in Synthesis Example 1, except that compounds 1-14 and 1- 68 and 1-96 were synthesized, respectively.

Synthesis Example 5. Synthesis of Compound 4-1

In the same manner as in Synthesis Example 1, except that (2-fluoro-[1,1′-biphenyl]-3-yl)boronic acid was used instead of (2-fluorophenyl) boronic acid in Synthesis Example 1, Compound 4-1 was synthesized.

Synthesis Example 6. Synthesis of Compound 2-1

4-Bromo-[1,1'-biphenyl]-3-ol (100 g, 401 mmol) and (3-chloro-2-fluorophenyl) boronic acid (70 g, 401 mmol) in a round bottom flask And dissolved in 2000 ml of tetrahydrofuran (THF). Potassium carbonate (111 g, 803 mmol) was dissolved in 500 ml of distilled water and added, and tetrakis (triphenylphosphine) palladium (0) (13.9 g, 12 mmol) was added. After refluxing for 2 hours and cooling, the organic layer was separated. After distillation under reduced pressure to remove tetrahydrofuran (THF), it was dissolved in chloroform, placed in a separatory funnel, and washed several times with water. Magnesium sulfate was added to the organic layer to remove water and then filtered. The filtrate was distilled under reduced pressure to remove the solvent. The obtained 3-chloro-2-fluoro-[1,1':4',1''-terphenyl]-2'-ol (87 g, 291 mmol) was directly used in the next reaction.

3-Chloro-2-fluoro-[1,1':4',1''-terphenyl]-2'-ol (87 g, 291 mmol) was added to a round bottom flask and dissolved in 700 ml of chloroform. The temperature was lowered to 0°C. After dissolving n-bromosuccinimide (52g, 291 mmol) in 100 ml of dimethylformamide, it was slowly added. After the addition was completed, the temperature was gradually raised to room temperature and then stirred for 1 hour. After the reaction solution and distilled water were added to a separatory funnel and extracted several times, only the organic layer was separated, and magnesium sulfate was added to remove water. Chloroform was removed by distillation under reduced pressure and purified by column chromatography. (73 g, 204 mmol)

5'-Bromo-3-chloro-2-fluoro-[1,1':4',1''-terphenyl]-2'-ol (73 g, 204 mmol), potassium carbonate (84.6 g, 612 mmol) and 500 ml of dimethylacetamide were added to a round bottom flask and stirred under reflux for 3 hours. After cooling, the reaction solution is poured into 1.5 L of distilled water. When a solid precipitated, it was filtered. After dissolving in 750 ml of chloroform, it was washed several times with distilled water using a separatory funnel. Magnesium sulfate was added to the organic layer to remove water and filtered. It was purified using column chromatography. (64 g, 179 mmol)

2-Bromo-6-chloro-3-phenyldibenzo[b,d]furan (64 g, 179 mmol), (10-phenylanthracene-9-yl) boronic acid (53.35 g, 179 mmol) with round bottom Put in a flask and dissolved in 500 ml of tetrahydrofuran (THF). Potassium carbonate (49.5 g, 358 mmol) was dissolved in 100 ml of distilled water and added, and tetrakis(triphenylphosphine)palladium(0) (6.20 g, 5.36 mmol) was added. The mixture was stirred at reflux for 18 hours and then cooled. The resulting solid was filtered and recrystallized with toluene to obtain 6-chloro-phenyl-2-(10-phenylanthracene-9-yl)dibenzo[b,d]furan (70 g, 131 mmol).

Put 6-chloro-phenyl-2-(10-phenylanthracene-9-yl)dibenzo[b,d]furan (70 g, 131 mmol) and phenylboronic acid (16.1 g, 131 mmol) in a round bottom flask. It was dissolved in 500 ml of tetrahydrofuran (THF). Potassium carbonate (34.6 g, 250 mmol) was dissolved in 100 ml of distilled water and added, and tetrakis(triphenylphosphine)palladium(0) (4.34 g, 3.76 mmol) was added. The mixture was stirred at reflux for 18 hours and then cooled. The resulting solid was filtered and recrystallized from toluene to obtain compound 2-1. (53 g, 92.5 mmol)

Synthesis Examples 7 to 9. Synthesis of Compounds 2-27, 2-73 and 2-183

In Synthesis Example 6, instead of (10-phenylanthracene-9-yl)boronic acid, (10-(naphthalen-2-yl)anthracene-9-yl)boronic acid, (10-(dibenzo[b,d]furan- Compound 2 in the same manner as in Synthesis Example 6 except that 2-yl)anthracene-9-yl)boronic acid and (4-(10-phenylanthracene-9-yl)naphthalen-1-yl)boronic acid were used respectively. -27, 2-73 and 2-183 were synthesized, respectively.

Synthesis Example 10. Synthesis of Compound 3-1

Synthesis Example 6, except that 3-bromo-[1,1'-biphenyl]-2-ol was used instead of 4-bromo-[1,1'-biphenyl]-3ol in Synthesis Example 6 In the same manner as, compound 3-1 was synthesized.

Synthesis Examples 11 to 13. Synthesis of compounds 3-14, 3-40 and 3-122

In Synthesis Example 6, 3-bromo-[1,1'-biphenyl]-2-ol was used instead of 4-bromo-[1,1'-biphenyl]-3ol, and (10-phenyl (10-(naphthalen-1-yl) anthracene-9-yl) boronic acid instead of anthracene-9-yl) boronic acid, 9-bromo-10-(phenanthrene-9-yl) anthracene, (4-(10 Compounds 3-14, 3-40, and 3-122 were synthesized in the same manner as in Synthesis Example 6, except that -(naphthalen-2-yl)anthracene-9-yl)phenyl)boronic acid was used, respectively.

Synthesis Examples 14 and 15. Synthesis of compounds 2-2 and 2-13.

Compounds 2-2 and 2-13 were prepared in the same manner except that naphthalen-1-ylboronic acid and [1,1'-biphenyl]-4-yl] boronic acid were used instead of phenyl boronic acid of Synthesis Example 6 Each was synthesized.

Synthesis Examples 16 and 17. Synthesis of compounds 3-3 and 3-13.

In Synthesis Example 6, 3-bromo-[1,1'-biphenyl]-2-ol was used instead of 4-bromo-[1,1'-biphenyl]-3ol, and naphthalene was used instead of phenyl boronic acid- Compounds 3-3 and 3-13 were synthesized in the same manner except that 2-ylboronic acid and [1,1'-biphenyl]-2-yl]boronic acid were used.

Synthesis Example 18. 2-8 Synthesis

2-bromo-5-chlorophenol (100 g, 482 mmol) and (2-fluoro-[1,1'-biphenyl]-3-yl) boronic acid (104 g, 482 mmol) in a round bottom flask And dissolved in 2500 ml of tetrahydrofuran (THF). Potassium carbonate (133 g, 964 mmol) was dissolved in 500 ml of distilled water and added, and tetrakis(triphenylphosphine)palladium(0) (410 mg, 0.80 mmol) was added. After refluxing for 2 hours and cooling, the organic layer was separated. After distillation under reduced pressure to remove tetrahydrofuran (THF), it was dissolved in chloroform, placed in a separatory funnel, and washed several times with water. Magnesium sulfate was added to the organic layer to remove water, and then filtered. The filtrate was distilled under reduced pressure to remove the solvent. The obtained 4-chloro-2'-fluoro-[1,1':3',1''-terphenyl]-2-ol (87 g, 291 mmol) was directly used in the next reaction.

4-Chloro-2'-fluoro-[1,1':3',1''-terphenyl]-2-ol (87 g, 291 mmol) was added to a round bottom flask and dissolved in 700 ml of chloroform. The temperature was lowered to 0°C. After dissolving n-bromosuccinimide (52 g, 292 mmol) in 100 ml of dimethylformamide, it was slowly added. After the addition was completed, the temperature was gradually raised to room temperature and then stirred for 1 hour. After the reaction solution and distilled water were added to a separatory funnel and extracted several times, only the organic layer was separated, and magnesium sulfate was added to remove water. Chloroform was removed by distillation under reduced pressure and purified by column chromatography. (66 g, 175 mmol)

5-Bromo-4-chloro-2'-fluoro-[1,1':3',1''-terphenyl]-2-ol (66 g, 174 mmol), potassium carbonate (72.5 g, 524 mmol) and 400 ml of dimethylacetamide were added to a round bottom flask and stirred under reflux for 3 hours. After cooling, the reaction solution is poured into 1.5 L of distilled water. When a solid precipitated, it was filtered. After dissolving in 750 ml of chloroform, it was washed several times with distilled water using a separatory funnel. Magnesium sulfate was added to the organic layer to remove water and filtered. It was purified using column chromatography. (47 g, 131 mmol)

2-bromo-3-chloro-6-phenyldibenzo[b,d]furan (47 g, 131 mmol), (10-phenylanthracene-9-yl) boronic acid (39.2 g, 131 mmol) with round bottom Put in a flask and dissolved in 500 ml of tetrahydrofuran (THF). Potassium carbonate (36.3 g, 263 mmol) was dissolved in 100 ml of distilled water and added, and tetrakis(triphenylphosphine)palladium(0) (4.55 g, 3.94 mmol) was added. The mixture was stirred at reflux for 18 hours and then cooled. The resulting solid was filtered and recrystallized from toluene. (45g, 84 mmol)

3-chloro-6-phenyl-2-(10-phenylanthracene-9-yl)dibenzo[b,d]furan (45 g, 84 mmol), phenylboronic acid (14.6 g, 84 mmol) in a round bottom flask And dissolved in 500 ml of tetrahydrofuran (THF). Potassium carbonate (23.4 g, 170 mmol) was dissolved in 100 ml of distilled water and added, and tetrakis (triphenylphosphine) palladium (0) (2.94 g, 2.54 mmol) was added. The mixture was stirred at reflux for 18 hours and then cooled. The resulting solid was filtered and recrystallized from toluene to obtain compound 2-8. (42g, 67 mmol)

Synthesis Example 19. Synthesis of Compound 2-11

Compounds 2-11 were each synthesized in the same manner except that dibenzo[b,d]furan-2-ylboronic acid was used instead of naphthalen-1-ylboronic acid of Synthesis Example 18.

Synthesis Example 20. Synthesis of Compound 3-8

Compound 3-8 was synthesized in the same manner as in Synthesis Example 18, except that 2-bromo-6-chlorophenol was used instead of 2-bromo-5-chlorophenol.

Synthesis Example 21. Synthesis of Compound 3-12

In Synthesis Example 18, 2-bromo-6-chlorophenol was used instead of 2-bromo-5-chlorophenol, and [1,1'-biphenyl]-3-yl] boron was used instead of naphthalen-1-ylboronic acid. Compound 3-12 was synthesized in the same manner except that an acid was used.

Synthesis Example 22. Synthesis of Compound 3-34

In Synthesis Example 18, 2-bromo-6-chlorophenol was used instead of 2-bromo-5-chlorophenol, and (10-(naphthalen-2-yl) was used instead of (10-phenylanthracene-9-yl) boronic acid. Compound 3-34 was synthesized in the same manner except that) anthracene-9-yl) boronic acid was used.

Synthesis Example 23. Synthesis of 4-7

The synthesized compound 1-1 (20g) and AlCl ₃ (4g) were added to C ₆ D ₆ (400ml) and stirred for 2 hours. After the reaction was completed, D ₂ O (60ml) was added, stirred for 30 minutes, and then trimethylamine (6ml) was added dropwise. The reaction solution was transferred to a separatory funnel, and extracted with water and toluene. The extract _{was dried over MgSO 4} and recrystallized with ethyl acetate to give compound 4-7 in a yield of 64%.

Synthesis Examples 24 and 25. Synthesis of 4-8 and 4-9

Compounds 4-8 and 4-9 were synthesized in the same manner as in Synthesis Example 23, except that compounds 2-1 and 3-1 were used instead of compound 1-1 in Synthesis Example 23.

The synthesized compounds of Synthesis Examples 1 to 25 are as follows.

Device Example 1. Preparation of Comparative Example 1.

A glass substrate coated with a thin film of 1,500Å of indium tin oxide (ITO) was placed in distilled water dissolved in a detergent and washed with ultrasonic waves. In this case, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. 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.

On the thus prepared ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 500Å to form a hole injection layer.

(HAT)

On the hole injection layer, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (400Å) of the following formula, which is a material for transporting holes, was vacuum deposited to form a hole transport layer Formed.

(NPB)

Subsequently, a light emitting layer was formed by vacuum depositing BH1 of the following formula as a light emitting layer host on the hole transport layer to a thickness of 300 Å.

(BH1)

While depositing the light emitting layer, 4% by weight of the compound BD 1 was used as a blue light emitting dopant.

(BD1)

On the light emitting layer, Alq ₃ (aluminum tris (8-hydroxyquinoline)) of the following formula was vacuum deposited to a thickness of 200 Å to form an electron injection and transport layer.

(Alq ₃ )

Lithium fluoride (LiF) in a thickness of 12 Å and aluminum in a thickness of 2,000 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 at 0.4 ~ 0.7 Å/sec, the deposition rate of lithium fluoride at the cathode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum degree during deposition was 2x10 ^-7. ~ 5x10 ^-8 torr was maintained.

The performance of the device manufactured as described above was measured.

Device Example 2. Preparation of Comparative Example 2.

The device performance was measured in the same manner as in Comparative Example 1, except that BH2 was used instead of BH1 as the blue light emitting layer host material.

(BH2)

Device Example 3. Preparation of Comparative Example 3.

The device performance was measured in the same manner as in Comparative Example 1, except that BH3 was used instead of BH1 as the blue light emitting layer host material.

(BH3)

Device Example 4. Preparation of Comparative Example 4.

The device performance was measured in the same manner as in Comparative Example 1, except that BH4 was used instead of BH1 as the blue light emitting layer host material.

(BH4)

Device Example 5. Preparation of Comparative Example 5.

The device performance was measured in the same manner as in Comparative Example 1, except that BH5 was used instead of BH1 as the host material for the blue light emitting layer.

(BH5)

Device Example 6. Preparation of Comparative Example 6.

The device performance was measured in the same manner as in Comparative Example 1, except that BH6 instead of BH1 was used as the blue light emitting layer host material.

(BH6)

Device Example 7. Preparation of Comparative Example 7.

The device performance was measured in the same manner as in Comparative Example 1, except that BH7 was used instead of BH1 as the blue light emitting layer host material.

(BH7)

Device Example 8. Preparation of Comparative Example 8.

The device performance was measured in the same manner as in Comparative Example 1, except that BH8 was used instead of BH1 as the blue light emitting layer host material.

(BH8)

Device Example 9. Preparation of Comparative Example 9.

The device performance was measured in the same manner as in Comparative Example 1, except that BH9 was used instead of BH1 as the blue light emitting layer host material.

(BH9)

Device Example 10. Preparation of Comparative Example 10.

The device performance was measured in the same manner as in Comparative Example 1, except that BH10 was used instead of BH1 as the blue light emitting layer host material.

(BH-10)

Device Example 11. Examples 1 to 16

The device performance was measured in the same manner as in Comparative Example 1, except that the compounds of Table 1 below were used instead of BH1 as a host material for the blue light emitting layer.

Element example Host material Driving voltage (V) Luminous efficiency (Cd/A) Color coordinate CIE_y Life T97%
(time) Comparative Example 1 BH1 4.57 6.12 0.046 91 Comparative Example 2 BH2 5.11 6.14 0.047 121 Comparative Example 3 BH3 5.25 5.90 0.046 129 Comparative Example 4 BH4 4.98 5.12 0.047 130 Comparative Example 5 BH5 4.85 5.15 0.046 121 Comparative Example 6 BH6 4.90 5.61 0.047 117 Comparative Example 7 BH7 4.98 5.02 0.056 80 Comparative Example 8 BH 8 4.98 5.32 0.046 112 Comparative Example 9 BH 9 4.85 5.21 0.045 131 Comparative Example 10 BH 10 4.90 5.15 0.043 123 Example 1 Compound 1-1 4.81 7.10 0.048 153 Example 2 Compound 1-14 4.76 7.05 0.048 160 Example 3 Compound 1-68 4.62 6.98 0.046 171 Example 4 Compound 1-96 4.72 6.85 0.045 159 Example 5 Compound 4-1 4.85 7.30 0.049 168 Example 6 Compound 2-1 4.82 6.81 0.045 167 Example 7 Compound 2-27 4.86 7.10 0.048 189 Example 8 Compound 2-73 4.56 7.23 0.047 175 Example 9 Compound 2-183 4.73 6.99 0.046 172 Example 10 Compound 3-1 4.72 7.01 0.045 163 Example 11 Compound 3-14 4.81 7.12 0.049 184 Example 12 Compound 3-40 4.84 7.19 0.048 175 Example 13 Compound 3-122 4.91 6.94 0.047 169 Example 14 Compound 2-2 4.85 7.21 0.046 180 Example 15 Compound 2-13 4.83 7.00 0.045 176 Example 16 Compound 3-3 4.75 7.30 0.048 169 Example 17 Compound 3-13 4.72 6.98 0.045 182 Example 18 Compound 2-8 4.81 7.02 0.046 170 Example 19 Compound 2-11 4.71 7.09 0.046 177 Example 20 Compound 3-8 4.69 6.99 0.047 183 Example 21 Compound 3-12 4.83 7.15 0.048 169 Example 22 Compound 3-34 4.75 7.22 0.045 189 Example 23 Compound 4-7 4.72 7.00 0.045 240 Example 24 Compound 4-8 4.82 6.78 0.045 255 Example 25 Compound 4-9 4.72 6.99 0.045 246

As in Comparative Examples 1 to 10 and Examples 1 to 25, the results of experimenting at a current density of ^{20 mA/cm 2} on an organic light-emitting device manufactured using each compound as a blue host material are shown in Table 1 above. The compounds of the comparative examples differ in the number and position of substituents substituted on the dibenzofuran group and the number of substituents bonded to the anthracene. It can be seen that when the compound of the present invention is applied to the device compared to the compound of the comparative example, the driving voltage is low and the efficiency and lifespan are increased.

1: substrate
2: first electrode
3: light-emitting layer
4: second electrode
5: hole injection layer
6: hole transport layer
7: electron injection and transport layer

Claims (10)

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

In Formula 1,
Ar1 is a phenyl group unsubstituted or substituted with deuterium or an aryl group, a naphthyl group unsubstituted or substituted with an aryl group, a biphenyl group, a terphenyl group, a phenanthrene group, a pyrene group, a fluoranthene group, a triphenylene group, or an aryl group substituted or unsubstituted A carbazole group, a dibenzofuran group, or a dibenzothiophene group,
Ar2 to Ar4 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
However, at least two of Ar2 to Ar4 are a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
L is a direct bond or a substituted or unsubstituted arylene group,
R1 and R2 are the same as or different from each other, and each independently hydrogen or deuterium,
R3 is the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted A substituted arylamine group, a substituted or unsubstituted alkyloxy group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted aryl group,
m to o are the same as or different from each other, and each independently an integer of 1 to 4,
When n is 2 or more, R1 is the same as or different from each other,
When m is 2 or more, R2 is the same as or different from each other,
When o is 2 or more, R3 is the same as or different from each other. The method of claim 1, wherein the formula 1 is a heterocyclic compound represented by any one of the following formulas 2 to 13:

In Formulas 2 to 13, Ar1 to Ar4, R1 to R3, and m to o are as defined in Formula 1. The method according to claim 1, wherein R3 is the same as or different from each other, and each independently, hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 10 carbon atoms, a substituted or unsubstituted An alkynyl group having 1 to 10 carbon atoms, an amine group substituted with an alkyl group having 1 to 10 carbon atoms, an amine group substituted with an aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkyloxy group having 1 to 10 carbon atoms, substituted or unsubstituted A heterocyclic compound that is a ringed aryloxy group having 6 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. The method according to claim 1, wherein Ar2 to Ar4 are the same as or different from each other, and each independently, an aryl group or a heteroaryl group,
The aryl group or heteroaryl group is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms A phosphine oxide group, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, an amine group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted A heterocyclic compound that is unsubstituted or substituted with one or more substituents selected from the group consisting of a cyclic C3 to C20 heteroaryl group. The heterocyclic compound of claim 1, wherein Formula 1 is any one selected from the following heterocyclic compounds:

A first electrode; A second electrode provided opposite to the first electrode; And one or two or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the heterocyclic compound of any one of claims 1 to 5 Phosphorus organic light emitting device. The organic light-emitting device of claim 6, wherein the organic material layer includes an emission layer, and the emission layer includes the heterocyclic compound. The organic light-emitting device of claim 7, wherein the emission layer includes a host and a dopant, and includes the heterocyclic compound as the host. The organic light-emitting device of claim 7, wherein the light-emitting layer comprises a compound of Formula A as a dopant:
[Formula A]

In Formula A,
X is B, P(=O) or P(=S),
A1 to A3 are the same as or different from each other, and each independently a monocyclic or polycyclic ring,
G1 to G3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Alkyl group; Aryl group; Heteroaryl group; Alkylamine group; A substituted or unsubstituted arylamine group; Or a heteroarylamine group, or may form a ring through Y3 by bonding with an adjacent group,
Y3 is a direct bond; O; C(Rm)(Rn); N(Rp); Or a substituted or unsubstituted silyl group,
Y1 and Y2 are the same as or different from each other, and each independently O or N(Rp),
Rm, Rn and Rp are the same as or different from each other, and each independently hydrogen, deuterium, an alkyl group, or a substituted or unsubstituted aryl group, or combine with an adjacent group to form a substituted or unsubstituted ring,
b1 to b3 are each an integer greater than or equal to 0,
When b1 to b3 are each 2 or more, the structures in the two or more parentheses are the same as or different from each other. The organic light-emitting device of claim 7, wherein the light-emitting layer includes any one of the following compounds as a dopant:

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