KR20200066231A - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides a compound represented by chemical formula 1 and an organic light emitting device comprising the same. The compound described in the present specification can be used as a material for an organic material layer of the organic light emitting device. The compound according to at least one embodiment can improve efficiency, lower a driving voltage, and/or improve lifespan characteristics in the organic light emitting device.

Description

Compound and organic light emitting device including same {COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

The present invention claims the benefit of the filing date of Korean Patent Application No. 10-2018-0152177, filed with the Korean Intellectual Property Office on November 30, 2018, all of which is incorporated herein.

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

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and electrons injected from two electrodes are combined and paired in an organic thin film, and then disappear and shine. The organic thin film may be composed of a single layer or multiple layers if necessary.

As a material used in the organic light emitting device, a pure organic material or a complex compound in which an organic material and a metal are complex occupies most, and depending on the purpose, a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. Can be divided into. Here, as a hole injection material or a hole transport material, an organic material having a p-type property, that is, an organic material that is easily oxidized and has an electrochemically stable state during oxidation, is mainly used. On the other hand, as an electron injection material or an electron transport material, an organic material having an n-type property, that is, an organic material having an easily reduced and electrochemically stable state during reduction is mainly used. The light-emitting layer material is preferably a material having both p-type and n-type properties, that is, a material having a stable form in both oxidation and reduction states, and excitons formed by recombination of holes and electrons in the light emitting layer are formed. A material with high luminous efficiency that converts it to light when desired is preferred.

In order to improve the performance, life or efficiency of the organic light emitting device, the development of an organic thin film material is continuously required.

Korean Patent Publication No. 10-2015-0132005

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

One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

[Formula 1]

In Chemical Formula 1,

X and Y are the same as or different from each other, and each independently O or S,

Z is N or CR,

R, R1 to R5, and R7 are the same as or different from each other, and each independently hydrogen; Nitrile group; heavy hydrogen; Halogen group; Carbonyl group; Ester groups; Imide group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthioxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkyl sulfoxy group; A substituted or unsubstituted aryl sulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may combine with an adjacent group to form a substituted or unsubstituted ring,

m and n are each independently an integer of 0 to 4, when m is 2 or more, R1 is the same or different from each other, and when n is 2 or more, R4 is the same or different from each other,

o, p, q, and w are each independently an integer of 0 to 3, and when o is 2 or more, R2 is the same or different from each other, when p is 2 or more, R3 is the same or different from each other, and when q is 2 or more, R5 Is the same as or different from each other, and when w is 2 or more, R7 is the same as or different from each other.

In addition, an exemplary embodiment of the present specification includes a first electrode; A second electrode; And an organic light emitting device including at least one layer of an organic material between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound of Formula 1.

The compounds described herein can be used as a material for the organic material layer of the organic light emitting device. The compound according to at least one exemplary embodiment may improve efficiency, low driving voltage, and/or lifespan characteristics in an organic light emitting device. The compounds described herein can be used as a material for a light emitting layer.

1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
Figure 2 is a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), electron blocking layer (7), light emitting layer (3), hole blocking layer (8), electron transport layer (9) , An example of an organic light emitting device in which the electron injection layer 10 and the cathode 4 are sequentially stacked.
3 is MS data of Compound 1.
4 is MS data of compound 4.
5 is MS data of compound 10.

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

One embodiment of the present specification provides the compound represented by Chemical Formula 1.

In the present specification, when a hetero ring formed of a 5-membered ring containing X of Formula 1 is included, the rigidity of the compound contained in the organic light emitting device can be increased, thereby increasing the heat resistance of the organic light emitting device. . In addition, this can have a high quantum efficiency, there is an advantage that can improve the life characteristics of the organic light emitting device by increasing the glass transition temperature.

In the present specification, each of the two benzene rings constituting the hetero ring containing X of Formula 1 is substituted with an n-type substituent and a p-type substituent.

In the present specification, when each of the two benzene rings constituting the hetero ring containing X of Formula 1 is substituted with an asymmetric position through an n-type substituent and a p-type substituent, an amorphous property is exhibited better. do. Accordingly, destruction of the device due to crystallization caused by joule heat generated during operation of the organic light emitting device can be prevented.

The term “substituted with an asymmetric position” means that each of the two benzene rings constituting the hetero ring containing X of Formula 1 is not substituted with the same carbon number as shown below.

In this specification, n-type means n-type semiconductor characteristics. In other words, the n-type is a property in which electrons are injected or transported through a LUMO (lowest unoccupied molecular orbital) energy level, which can be defined as a property of a material having greater electron mobility than hole mobility. Conversely, p-type refers to p-type semiconductor characteristics. In other words, p-type is a property in which holes are injected or transported through a HOMO (highest occupied molecular orbital) energy level, which can be defined as a property of a material whose hole mobility is greater than electron mobility.

In the present specification, when the compound represented by Chemical Formula 1 is used in the organic material layer of the organic light emitting device, not only the efficiency of the organic light emitting device is always, but also has a low driving voltage and has excellent lifespan characteristics.

In the present invention, in particular, the voltage of the organic light emitting device can be lowered by including the compound represented by Chemical Formula 1 and the thermally activated delayed fluorescent compound together in the organic material layer of the organic light emitting device.

In the present specification, HOMO (highest occupied molecular orbital) means a molecular orbital function (highest occupied molecular orbital) in the region with the highest energy in the region where electrons can participate in binding, and LUMO (lowest unoccupied molecular orbital). The term "molecular orbital function" (lowest unoccupied molecular orbital) in which the electron is in the lowest energy region of the semi-bonding region, and the HOMO energy level means the distance from the vacuum level to the HOMO. In addition, LUMO energy level means the distance from a vacuum level to LUMO.

In this specification, the bandgap (bandgap) means a difference in energy levels between HOMO and LUMO, that is, a HOMO-LUMO gap.

In the present specification, the HOMO energy level of the compound represented by Chemical Formula 1 is 6.2eV to 5.5eV, and the LUMO energy level is 2.8eV to 2.3eV, which has an appropriate value and is used together with a thermally activated delayed fluorescent compound. , It is possible to lower the voltage of the organic light emitting device.

In this specification, in particular, when a dibenzofuranyl group is introduced based on the heterocycle containing X in Chemical Formula 1, HOMO and LUMO energy levels have appropriate values, thereby lowering the voltage of the organic light emitting device.

In the present specification, the HOMO energy level is measured by irradiating UV on the surface of the thin film, and detecting a protruding electron at this time, a UPS (UV photoelectron spectroscopy) that measures the ionization potential of the material can be used. . Alternatively, the HOMO energy level can be measured by cyclic voltammetry (CV) measuring the oxidation potential through a voltage sweep after dissolving the material to be measured in a solvent together with an electrolyte. When measuring the HOMO energy level in the form of a thin film, the UPS can measure a more accurate value than the CV, and the HOMO energy level of the present specification was measured through the UPS method.

In the present specification, the LUMO energy level can be obtained by measuring IPES (Inverse Photoelectron Spectroscopy) or electrochemical reduction potential. IPES is a method of determining the LUMO energy level by irradiating an electron beam to a thin film and measuring the light emitted at this time. In addition, in the measurement of the electrochemical reduction potential, a reduction potential may be measured through a voltage sweep after dissolving the material to be measured in a solvent together with an electrolyte. Alternatively, the LUMO energy level can be calculated using the singlet energy level obtained by measuring the HOMO energy level and the degree of UV absorption of the target material.

In the present specification, when a part is to “include” a certain component, it means that the component may further include other components, not to exclude other components, unless otherwise stated.

In the present specification, when a member is said to be positioned “on” another member, this includes not only the case where one member is in contact with the other member but also another member between the two members.

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

In this specification, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Ar alkenyl group; Alkyl aryl groups; Arylphosphine group; And substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl groups, or substituted or unsubstituted with two or more of the substituents exemplified above. For example, "a substituent having two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.

In the present specification, the “adjacent” group refers to a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest to the substituent and the other substituent substituted on the atom in which the substituent is substituted. Can be. For example, two substituents substituted in the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" to each other.

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

In this specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms.

In the present specification, the oxygen of the ester group may be substituted with a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms.

In this specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms.

In the present specification, the silyl group may be represented by the formula of -SiR ₁₁ R ₁₂ R ₁₃ , wherein R _11, R ₁₂ and R ₁₃ are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. Does not.

In the present specification, the alkyl group may be straight chain or branched chain, and carbon number 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. Specific examples of the alkyl group are 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-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-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited to these.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. 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, and the like, but is not limited thereto.

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -Hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. It is not limited.

Substituents comprising alkyl, alkoxy, and other alkyl group moieties described herein include both straight-chain or ground forms.

In the present specification, the aryloxy group is not particularly limited, but is preferably 6 to 60 carbon atoms. Specifically, the phenoxy group, biphenoxy group, naphthoxy group, binaphthoxy group, anthracenox group, phenanthrenoxy group, fluorenoxy group, and the like, but are not limited to these.

In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styrenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group. The aryl group in the arylphosphine group may be a monocyclic aryl group or a polycyclic aryl group. The arylphosphine 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.

In the present specification, the aryl group 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 one embodiment, the carbon number of the aryl group is 6 to 40. According to one embodiment, the carbon number of the aryl group is 6 to 20. According to one embodiment, the carbon number of the aryl group is 6 to 12. The monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or a quarterphenyl group, but is not limited thereto. The polycyclic aryl group includes a naphthyl group, anthracenyl group, phenanthrenyl group, perillynyl group, fluoranthenyl group, triphenylenyl group, phenenyl group, pyrenyl group, tetrasenyl group, chrysenyl group, pentacene group , A fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzofluorenyl group, or a spirofluorenyl group, but is not limited thereto.

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

(스피로[시클로펜탄-1,9'-플루오렌]),

(9,9'-스피로바이[플루오렌]) 등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기) 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

(Spiro[cyclopentane-1,9'-fluorene]),

Spirofluorenyl groups such as (9,9'-spirobi [fluorene]),

(9,9-dimethylfluorenyl group) and

It may be a substituted fluorenyl group, such as (9,9-diphenylfluorenyl group). However, it is not limited thereto.

In the present specification, a heteroaryl group is a heteroaryl group containing one or more of N, O, and S, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the heteroaryl group has 2 to 40 carbon atoms. According to one embodiment, the carbon number of the heteroaryl group is 2 to 20. According to one embodiment, the heteroaryl group has 2 to 12 carbons. Examples of the heteroaryl group include pyridyl group, pyrrol group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazole group, pyrazole group, oxazole group, isooxazole group, thiazole group, isothiazole group, triazole group , Oxadiazole group, thiadiazole group, dithiazole group, tetrazol group, pyranyl group, thiopyranyl group, pyrazinyl group, oxazinyl group, thiazinyl group, dioxynyl group, triazinyl group, tetrazinyl group, quinolinyl group , Isoquinolinyl group, quinolyl group, quinazolinyl group, quinoxalinyl group, naphthyridinyl group, acridil group, xanthenyl group, phenanthridinyl group, diazanaphthalenyl group, triazindenyl group, indole group, indole group Linyl group, indolizinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, benzothiazole group, benzoxazole group, benzimidazole group, benzothiophene group, benzo Furanyl group, dibenzothiophenyl group, dibenzofuranyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, indolocarbazolyl group, indenocarbazolyl group, phenazinyl group, imidazopyridine group, pe Noxazinyl group, phenanthridine group, phenanthroline group, phenothiazine group, imidazopyridine group, imidazophenanthridine group. Benzoimidazoquinazoline groups, or benzoimidazophenanthridine groups, and the like, but are not limited thereto.

In the present specification, the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group, arylphosphine group, aralkyl group, aralkylamine group, aralkenyl group, alkylaryl group, arylamine group, and arylheteroarylamine group is described above. A description of one aryl group can be applied.

In the present specification, the alkyl group of the alkylthio group, the alkyl sulfoxy group, the aralkyl group, the aralkylamine group, the alkylaryl group, and the alkylamine group, the description of the aforementioned alkyl group may be applied.

In the present specification, the alkenyl group among the alkenyl groups may be applied to the alkenyl group described above.

In the present specification, the meaning of forming a ring by bonding with adjacent groups to form a ring is a substituted or unsubstituted aliphatic hydrocarbon ring by combining with adjacent groups; Substituted or unsubstituted aromatic rings; Substituted or unsubstituted aliphatic hetero rings; A substituted or unsubstituted aromatic hetero ring; Or it means forming these condensed rings.

In the present specification, the aliphatic hydrocarbon ring means a ring consisting only of carbon and hydrogen atoms as a ring that is not aromatic. Specifically, examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, etc. There is, but is not limited to these.

In the present specification, an aromatic ring means an aromatic ring composed of only carbon and hydrogen atoms. Specifically, examples of the aromatic ring include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenane, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene , Benzofluorene, spirofluorene, and the like, but are not limited thereto.

In the present specification, an aliphatic hetero ring means an aliphatic ring containing one or more of hetero atoms. Specifically, examples of the aliphatic hetero ring include oxirane, tetrahydrofuran, 1,4-dioxane (1,4-dioxane), pyrrolidine, piperidine, morpholine, oxepan , Azocaine, thiocaine, etc., but are not limited to these.

In the present specification, an aromatic hetero ring means an aromatic ring containing one or more of hetero atoms. Specifically, examples of the aromatic heterocycle include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole , Thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinol, quinazoline, quinoxaline, naphthyridine, ah Credine, phenanthridine, diazanaphthalene, triazainden, indole, indolizine, benzothiazole, benzoxazole, benzoimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole , Benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, phenanthridine, indolocarbazole, indenocarbazole, and the like, but are not limited thereto.

According to an exemplary embodiment of the present specification, R are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Carbonyl group; Ester groups; Imide group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthioxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkyl sulfoxy group; A substituted or unsubstituted aryl sulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heteroaryl group, or may combine with an adjacent group to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, R is hydrogen; A substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heteroaryl group, or combine with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted hetero ring.

According to an exemplary embodiment of the present specification, R is hydrogen; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 40 carbon atoms in combination with an adjacent group, a substituted or unsubstituted aromatic ring having 6 to 40 carbon atoms, or It may form an unsubstituted heterocycle having 2 to 40 carbon atoms.

According to an exemplary embodiment of the present specification, R is hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms in combination with an adjacent group, a substituted or unsubstituted aromatic ring having 6 to 30 carbon atoms, or It may form an unsubstituted heterocycle having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R is hydrogen; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms in combination with an adjacent group, a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms, or It may form an unsubstituted heterocycle having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R is hydrogen; A substituted or unsubstituted aryl group having 6 to 12 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms, or an adjacent hydrocarbon group substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 12 carbon atoms, a substituted or unsubstituted aromatic ring having 6 to 12 carbon atoms, or It may form an unsubstituted heterocycle having 2 to 12 carbon atoms.

According to an exemplary embodiment of the present specification, R is hydrogen; A substituted or unsubstituted phenyl group; It may be a substituted or unsubstituted carbazole group, or combine with adjacent groups to form a substituted or unsubstituted fluorene, dibenzothiophene, dibenzofuran or carbazole.

According to an exemplary embodiment of the present specification, R is hydrogen.

According to an exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Carbonyl group; Ester groups; Imide group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthioxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkyl sulfoxy group; A substituted or unsubstituted aryl sulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heteroaryl group, or may combine with an adjacent group to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heteroaryl group, or combine with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted hetero ring.

According to an exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 40 carbon atoms in combination with an adjacent group, a substituted or unsubstituted aromatic ring having 6 to 40 carbon atoms, or It may form an unsubstituted heterocycle having 2 to 40 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms in combination with an adjacent group, a substituted or unsubstituted aromatic ring having 6 to 30 carbon atoms, or It may form an unsubstituted heterocycle having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms in combination with an adjacent group, a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms, or It may form an unsubstituted heterocycle having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group having 6 to 12 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms, or an adjacent hydrocarbon group substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 12 carbon atoms, a substituted or unsubstituted aromatic ring having 6 to 12 carbon atoms, or It may form an unsubstituted heterocycle having 2 to 12 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted phenyl group; Or it may be a substituted or unsubstituted carbazole group, or may combine with adjacent groups to form a substituted or unsubstituted fluorene, dibenzothiophene, dibenzofuran or carbazole.

According to an exemplary embodiment of the present specification, R1 is hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, R1 is hydrogen; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

According to an exemplary embodiment of the present specification, R1 is hydrogen; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R1 is hydrogen; A substituted or unsubstituted aryl group having 6 to 12 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms.

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

According to an exemplary embodiment of the present specification, R1 is an aryl group having 6 to 12 carbon atoms substituted with any one or more selected from the group consisting of deuterium, nitrile group, alkyl group, aryl group, and heteroaryl group.

According to an exemplary embodiment of the present specification, R1 is a heteroaryl group having 2 to 12 carbon atoms, which is substituted with any one or more selected from the group consisting of deuterium, nitrile group, alkyl group, aryl group, and heteroaryl group.

According to an exemplary embodiment of the present specification, R1 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted terphenyl group; Or a substituted or unsubstituted anthracene group.

According to an exemplary embodiment of the present specification, R1 is a phenyl group unsubstituted or substituted with an alkyl group; A biphenyl group unsubstituted or substituted with an alkyl group; A naphthyl group unsubstituted or substituted with an alkyl group; A terphenyl group unsubstituted or substituted with an alkyl group; Or an anthracene group unsubstituted or substituted with an alkyl group.

According to an exemplary embodiment of the present specification, R1 is a phenyl group unsubstituted or substituted with an aryl group; A biphenyl group unsubstituted or substituted with an aryl group; A naphthyl group unsubstituted or substituted with an aryl group; A terphenyl group unsubstituted or substituted with an aryl group; Or an anthracene group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, R1 is a phenyl group unsubstituted or substituted with a heteroaryl group; A biphenyl group unsubstituted or substituted with a heteroaryl group; A naphthyl group unsubstituted or substituted with a heteroaryl group; A terphenyl group unsubstituted or substituted with a heteroaryl group; Or an anthracene group unsubstituted or substituted with a heteroaryl group.

According to an exemplary embodiment of the present specification, R1 is hydrogen; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted carbazolyl group.

According to an exemplary embodiment of the present specification, R1 is hydrogen; Phenyl group; Or a carbazolyl group.

According to an exemplary embodiment of the present specification, R2 is hydrogen; A substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heteroaryl group, or combine with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted hetero ring.

According to an exemplary embodiment of the present specification, R2 is hydrogen; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 40 carbon atoms in combination with an adjacent group, a substituted or unsubstituted aromatic ring having 6 to 40 carbon atoms, or It may form an unsubstituted heterocycle having 2 to 40 carbon atoms.

According to an exemplary embodiment of the present specification, R2 is hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms in combination with an adjacent group, a substituted or unsubstituted aromatic ring having 6 to 30 carbon atoms, or It may form an unsubstituted heterocycle having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R2 is hydrogen; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms in combination with an adjacent group, a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms, or It may form an unsubstituted heterocycle having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R2 is hydrogen; A substituted or unsubstituted aryl group having 6 to 12 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms, or an adjacent hydrocarbon group substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 12 carbon atoms, a substituted or unsubstituted aromatic ring having 6 to 12 carbon atoms, or It may form an unsubstituted heterocycle having 2 to 12 carbon atoms.

According to an exemplary embodiment of the present specification, R2 is hydrogen; A substituted or unsubstituted aryl group having 6 to 12 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms.

According to an exemplary embodiment of the present specification, R2 is bonded to an adjacent group with each other, substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms, substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms, or substituted or unsubstituted Heterocycle of 2 to 20 carbon atoms is formed.

According to another exemplary embodiment, R2 is hydrogen; A substituted or unsubstituted phenyl group; Or it may be a substituted or unsubstituted carbazolyl group, or may be combined with adjacent groups to form a substituted or unsubstituted fluorene, dibenzothiophene, dibenzofuran or carbazole.

According to another exemplary embodiment, R2 is hydrogen; Phenyl group; Or it may be a carbazolyl group, or combine with an adjacent group to form a carbazole substituted with a fluorene, dibenzothiophene, dibenzofuran, or phenyl group substituted with a methyl group.

According to one embodiment of the present specification, R3 to R5 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present specification, R3 to R5 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

According to one embodiment of the present specification, R3 to R5 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

According to one embodiment of the present specification, R3 to R5 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group having 6 to 12 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms.

According to one embodiment of the present specification, R3 to R5 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted carbazolyl group.

According to another exemplary embodiment, R3 to R5 are the same as or different from each other, and each independently hydrogen; Phenyl group; Or a carbazolyl group.

According to another exemplary embodiment, R3 to R5 are hydrogen.

According to an exemplary embodiment of the present specification, R7 is hydrogen.

According to an exemplary embodiment of the present specification, R3 is a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, R4 is a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, R5 is a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, R3 is a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, R4 is a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, R5 is a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, the formula 1 is represented by the following formula 2 or 3.

[Formula 2]

[Formula 3]

In Formula 2 and Formula 3,

The definitions of X, Y, Z, R, R1 to R5, R7, m, n, o, p, q and w are as defined in Formula 1.

According to an exemplary embodiment of the present specification, the formula 1 is represented by the following formula (4).

[Formula 4]

In Chemical Formula 4,

The definitions of Y, R1 to R5, R7, m, n, p, q and w are the same as those in Formula 1,

X ₁ is O or S,

X ₂ is O, S, CR'R'' or NR''',

The definitions of R', R'', R''' and R6 are the same as those of R, R1 to R5 and R7 in the formula (1),

r is an integer from 0 to 2, and when r is 2, R2 is the same as or different from each other,

s is an integer from 0 to 4, and when s is 2 or more, R6 is the same or different from each other.

According to an exemplary embodiment of the present specification, the formula 1 is represented by the following formula 2-1 or 3-1.

[Formula 2-1]

[Formula 3-1]

In Chemical Formulas 2-1 and 3-1,

The definitions of Y, R1 to R5, m, n, p and q are the same as those in Formula 1,

X ₁ is O or S,

X ₂ is O, S, CR'R'' or NR''',

The definitions of R', R'', R''' and R6 are the same as those of R, R1 to R5 and R7 in the formula (1),

r is an integer from 0 to 2, and when r is 2, R2 is the same as or different from each other,

s is an integer from 0 to 4, and when s is 2 or more, R6 is the same or different from each other.

According to one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 2-1-1 to 2-1-6.

[Formula 2-1-1]

[Formula 2-1-2]

[Formula 2-1-3]

[Formula 2-1-4]

[Formula 2-1-5]

[Formula 2-1-6]

In the above formula 2-1-1 to 2-1-6,

The definitions of Y, R1 to R5, m, n, p and q are the same as those in Formula 1,

X ₁ is O or S,

X ₂ is O, S, CR'R'' or NR''',

The definitions of R', R'', R''' and R6 are the same as those of R, R1 to R5 and R7 in the formula (1),

r is an integer from 0 to 2, and when r is 2, R2 is the same as or different from each other,

s is an integer from 0 to 4, and when s is 2 or more, R6 is the same or different from each other.

According to one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 3-1-1 to 3-1-6.

[Formula 3-1-1]

[Formula 3-1-2]

[Formula 3-1-3]

[Formula 3-1-4]

[Formula 3-1-5]

[Formula 3-1-6]

In Chemical Formulas 3-1-1 to 3-1-6,

The definitions of Y, R1 to R5, m, n, p and q are the same as those in Formula 1,

X ₁ is O or S,

X ₂ is O, S, CR'R'' or NR''',

The definitions of R', R'', R''' and R6 are the same as those of R, R1 to R5 and R7 in the formula (1),

r is an integer from 0 to 2, and when r is 2, R2 is the same as or different from each other,

s is an integer from 0 to 4, and when s is 2 or more, R6 is the same or different from each other.

According to an exemplary embodiment of the present specification, the R', R'' and R''' are the same as or different from each other, and each independently substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to another exemplary embodiment, R', R'' and R''' are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.

According to an exemplary embodiment of the present invention, R', R'' and R''' are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, R', R'' and R''' are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

According to another exemplary embodiment, R', R'' and R''' are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

According to an exemplary embodiment of the present specification, the R', R'' and R''' are the same as or different from each other, and each independently an alkyl group; Or an aryl group.

According to another exemplary embodiment, R', R'' and R''' are the same as or different from each other, and each independently an alkyl group having 1 to 40 carbon atoms; Or an aryl group having 6 to 40 carbon atoms.

According to an exemplary embodiment of the present invention, the R', R'' and R''' are the same as or different from each other, and each independently an alkyl group having 1 to 30 carbon atoms; Or an aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present invention, the R', R'' and R''' are the same as or different from each other, and each independently an alkyl group having 1 to 20 carbon atoms; Or an aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present invention, the R', R'' and R''' are the same as or different from each other, and each independently an alkyl group having 1 to 10 carbon atoms; Or an aryl group having 6 to 12 carbon atoms.

According to an exemplary embodiment of the present invention, the R', R'' and R''' are the same as or different from each other, and each independently a methyl group; Ethyl group; Propyl group; Isopropyl group; Butyl group; Terbutyl group; Phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Anthracene group; Phenanthrene group; Triphenylene group; Fluorene group; Or pyrene.

According to an exemplary embodiment of the present invention, the R', R'' and R''' are the same as or different from each other, and each independently a methyl group; Ethyl group; Propyl group; Isopropyl group; Butyl group; Or a terbutyl group.

According to an exemplary embodiment of the present invention, the R', R'' and R''' are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Anthracene group; Phenanthrene group; Triphenylene group; Fluorene group; Or pyrene.

According to an exemplary embodiment of the present invention, the R', R'' and R''' are the same as or different from each other, and each independently a methyl group; Ethyl group; Propyl group; Isopropyl group; Butyl group; Terbutyl group; Phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Or anthracene group.

According to another exemplary embodiment, R', R'' and R''' are the same as or different from each other, and each independently a methyl group; Or a phenyl group.

In one embodiment of the present specification, R'and R'' are methyl groups.

In one embodiment of the present specification, R'and R'' are phenyl groups.

In one embodiment of the present specification, R″' is a methyl group.

In one embodiment of the present specification, R″' is a phenyl group.

According to an exemplary embodiment of the present specification, R6 is hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, R6 is hydrogen; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

According to an exemplary embodiment of the present specification, R6 is hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R6 is hydrogen; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R6 is hydrogen; A substituted or unsubstituted aryl group having 6 to 12 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms.

According to an exemplary embodiment of the present specification, R6 is hydrogen; An aryl group having 6 to 40 carbon atoms; Or a heteroaryl group having 2 to 40 carbon atoms.

According to an exemplary embodiment of the present specification, R6 is hydrogen; An aryl group having 6 to 30 carbon atoms; Or a heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R6 is hydrogen; An aryl group having 6 to 20 carbon atoms; Or a heteroaryl group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R6 is hydrogen; An aryl group having 6 to 12 carbon atoms; Or a heteroaryl group having 2 to 12 carbon atoms.

According to an exemplary embodiment of the present specification, R6 is hydrogen; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted carbazolyl group.

According to an exemplary embodiment of the present specification, R6 is hydrogen; A phenyl group unsubstituted or substituted with an alkyl group or an aryl group; Or a carbazolyl group unsubstituted or substituted with an alkyl group or an aryl group.

According to another exemplary embodiment, R6 is hydrogen; Phenyl group; Or a carbazolyl group.

According to an exemplary embodiment of the present specification, R6 is hydrogen.

According to an exemplary embodiment of the present specification, R7 is hydrogen.

In one embodiment of the present specification, X is O.

In one embodiment of the present specification, X is S.

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

In one embodiment of the present specification, Y is S.

In one embodiment of the present specification, Z is N.

In one embodiment of the present specification, Z is CR.

In another exemplary embodiment, X ₁ is O.

In another exemplary embodiment, X ₁ is S.

In one embodiment of the present specification, X ₂ is O.

In one embodiment of the present specification, X ₂ is S.

In one embodiment of the present specification, X ₂ is CR'R''.

In one embodiment of the present specification, X ₂ is NR′''.

In one embodiment of the present specification, Chemical Formula 1 may be any one selected from the following compounds.

The compound according to an exemplary embodiment of the present specification may be prepared by a manufacturing method described later. This is for understanding, and the method for preparing the compound of the present invention is not limited to the following manufacturing method.

For example, the compound of Formula 1 may have a core structure as shown in the following scheme. Substituents can be combined by methods known in the art, and the type, location, or number of substituents can be varied according to techniques known in the art.

는 추가의 치환기가 결합될 수 있음을 의미한다.In the above reaction formula

Means that additional substituents can be attached.

Synthesis of Intermediate A

Under nitrogen, 0.4 mol of 4-bromodibenzofuran or 4-bromodibenzothiophene, 0.2 mol of iodine and 0.2 mol of phenyl iodide diacetate were added to a mixed solution of 150 ml acetic acid and 150 ml acetic anhydride. After adding and adding three drops of sulfuric acid, the mixture was stirred at room temperature for 10 hours. After completion of the reaction, ethyl acetate was added to the mixed solution, followed by washing with water, separating the layers, receiving only the organic layer, adding anhydrous magnesium sulfate, and stirring. After filtering the silica pad, the solution was concentrated under reduced pressure to purify the column, and the intermediate A was obtained in 65% yield.

Synthesis of Intermediate B

0.2 mol of intermediate A, 0.2 mol of carbazole, 0.3 mol of copper powder and 0.2 mol of potassium carbonate were added to 70 ml dimethyl acetoamide and stirred at 130°C for 24 hours. After completion of the reaction, after cooling to room temperature, the silica pad was filtered to remove copper powder, and the obtained solution was washed with water, and then only an organic layer was received and anhydrous magnesium sulfate was added and stirred. After filtering the silica pad, the solution was concentrated under reduced pressure to purify the column, and the intermediate B was obtained in 78% yield.

Synthesis of Compounds C1 and C2

Intermediate B 0.3 mol, 1 (or 4)-dibenzofuran (or dibenzothiophene) boronic acid 0.33 mol and tetrakistriphenylphosphine palladium (Tetrakis(triphenylphosphine)palladium) 2 mol% in 50 ml of tetrahydrofuran and potassium 0.6 mol of carbonate was dissolved in 25 ml of water and mixed. After stirring at 80°C for 12 hours, the reaction was terminated and cooled to room temperature to separate water and organic layers. Anhydrous magnesium sulfate was added to the organic layer, followed by stirring. After filtering the silica pad, the solution was concentrated under reduced pressure to purify the column, and the compounds C1 and C2 were obtained in 60% yield.

In addition, the present specification provides an organic electroluminescent device comprising the above-described compound.

In one embodiment of the present application, the first electrode; A second electrode provided to face the first electrode; And an organic electroluminescent device including at least one organic layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound.

The organic material layer of the organic electroluminescent device of the present application may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, as a typical example of the organic electroluminescent device of the present invention, the organic electroluminescent device 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 as an organic material layer. However, the structure of the organic electroluminescent device is not limited to this, and may include fewer organic layers.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer contains the compound.

In one embodiment of the present application, the light emitting layer includes a host and a dopant.

In one embodiment of the present application, the light-emitting layer includes the compound as a host.

In one embodiment of the present application, the light-emitting layer includes the compound as a phosphorescent host.

In one embodiment of the present application, the light emitting layer includes a host and a dopant in a mass ratio of 99:1 to 1:99.

In one embodiment of the present application, the light emitting layer includes a host and a dopant in a mass ratio of 99:1 to 10:90.

In one embodiment of the present application, the light emitting layer includes a host and a dopant in a mass ratio of 99:1 to 45:55.

In one embodiment of the present application, the light emitting layer may use a metal complex as a dopant, but is not limited thereto.

In one embodiment of the present application, the light emitting layer uses an iridium complex as a dopant.

In one embodiment of the present application, the light emitting layer may use the following iridium complex as a dopant, but this is only an example and is not limited thereto.

In another exemplary embodiment, the light emitting layer including the compound represented by Chemical Formula 1 may include a compound represented by Chemical Formula 1 as a host, and a thermally activated delayed fluorescent compound as a dopant.

In the present specification, the thermally activated delayed fluorescence compound refers to a compound that exhibits a phenomenon leading to fluorescence by generating heat energy by inducing reverse energy transfer from the lowest excited triplet state (T ₁ ) to the lowest excited singlet state (S ₁ ). it means.

In the present specification, delayed fluorescence refers to fluorescence in which triplet excitons emit light by performing reverse-intersystem crossing with singlet excitons.

In the present specification, the lowest excited triplet state (T ₁ ) is the energy of the triplet state having the lowest energy.

In the present specification, a triplet state means a state in which the sum of the quantum numbers of the spin angular momentum of the entire electron is 1.

In the present specification, the lowest excited singlet state (S ₁ ) is the energy of the singlet state having the lowest energy.

In the present specification, a singlet state means a state in which the sum of the quantum numbers of the spin angular momentum of the entire electron is zero.

In the present specification, the energy of the lowest excited triplet state (T ₁ ) and the lowest excited singlet state (S ₁ ) is determined by quantum chemical calculation.

The photoluminescence spectrum in the solid state (energy level in the lowest singlet state) and the photoluminescence spectrum in the low temperature state (the energy level in the lowest triplet state) are measured, and the photoluminescence spectrum in the solid state is manufactured by Perkin Elmer. It was measured using LS-55, and the emission spectrum at an excitation wavelength of 370 nm was 400 nm to 660 nm, and HPLC grade THF (tetrahydrofuran) was used as a solvent, and the content of the compound was 1X10 ^-6 M. The photoluminescence spectrum at a low temperature was measured using LS-55 of Perkin Elmer, and the emission spectrum at an excitation wavelength of 445 nm is 400 nm to 700 nm. HPLC grade THF was used as the solvent, and it was measured under liquid nitrogen.

In the present specification, the difference (ΔE _st ) between the lowest excited triplet state (T ₁ ) and the lowest excited singlet state (S ₁ ) of the thermally activated delayed fluorescence compound is 0.2 eV or less (0 eV is not included). desirable.

In the present specification, when the difference (ΔE _st ) between the lowest excited triplet state (T ₁ ) and the lowest excited singlet state (S ₁ ) is small, preferably 0.2 eV or less, the singlet exciton emits light as it is. (Ie, fluorescence), and triplet excitons are reversed-intersystem crossing with singlet excitons (ie, delayed fluorescence). Accordingly, since the delayed fluorescence mechanism is added to light emission by the fluorescence mechanism, it may be possible to increase the internal quantum efficiency to 100%.

When the difference (△E _st ) between the lowest excitation triplet state (T ₁ ) and the lowest excitation singlet state (S ₁ ) is greater than 0.2 eV, there is less phenomenon that natural fluorescence occurs due to the relatively inverse interphase transition. Can lose.

In the present specification, the energy (Eg _S ) in the singlet state of the thermally activated delayed fluorescent compound and the energy (Eg _77K ) in _77K can be expressed by the following equation.

△ST= Eg _S -Eg _77K <0.3eV

In the above equation, Eg _S and Eg _77K are values that can be measured through the energy level measurement methods of the singlet state and triplet state described above, respectively. When the difference is small and the above equation is satisfied, transitions between inverses are smooth and natural. Fluorescence is generated.

In the present specification, the mixture of the compound represented by Chemical Formula 1 and the thermally activated delayed fluorescent compound is represented by │HOMO(Host)│>│HOMO(TADF)│ in order to prevent the exciplex formation of the light emitting layer, It is preferable that S ₁ (Host)>2.8 eV and HOMO (Host)≧5.8 eV.

The exciplex of the light emitting layer refers to a complex formed by a combination of excited and ground molecules between two different molecules.

In an exemplary embodiment of the present specification, when the compound represented by Chemical Formula 1 and the heat activated delayed fluorescent compound are used together, the compound of Chemical Formula 1 may be 99 to 45 parts by weight based on 100 parts by weight of the host, and delay the thermal activation The fluorescent compound may be 1 to 55 parts by weight based on 100 parts by weight of the host.

In one embodiment of the present specification, the thermally activated delayed fluorescent compound may be any one selected from the following compounds, but is not limited thereto.

In one embodiment of the present application, the organic material layer includes a hole injection layer or a hole transport layer.

In one embodiment of the present application, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.

In one embodiment of the present application, the organic material layer includes a hole injection layer, a hole transport layer or a hole injection and transport layer.

In one embodiment of the present application, the organic material layer includes a hole injection layer, a hole transport layer or a hole injection and transport layer, and the hole injection layer, a hole transport layer or a hole injection and transport layer contains the compound.

In an exemplary embodiment of the present application, the organic material layer includes an electron transport layer or an electron injection layer.

In one embodiment of the present application, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer contains the compound.

In one embodiment of the present application, the organic material layer includes a hole injection layer, a hole transport layer or a hole injection and transport layer.

In one embodiment of the present application, the organic material layer includes a hole injection layer, a hole transport layer or a hole injection and transport layer, and the hole injection layer, a hole transport layer or a hole injection and transport layer contains the compound.

In one embodiment of the present application, the organic material layer includes an electron blocking layer or a hole blocking layer.

In one embodiment of the present application, the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or hole blocking layer includes the compound.

In one embodiment of the present application, the organic electroluminescent device includes a first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. It includes two or more organic material layers provided between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode, and at least one of the two or more organic material layers comprises the compound.

In another exemplary embodiment, the organic electroluminescent device may be an organic light emitting device having a structure in which an anode, one or more organic material layers and a cathode are sequentially stacked on a substrate.

In another embodiment, the organic electroluminescent 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.

For example, the structure of the organic electroluminescent device according to an exemplary embodiment of the present application is illustrated in FIG. 1.

1 illustrates a structure of an organic electroluminescent device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked. In this structure, the compound may be included in the light emitting layer (3).

Figure 2 is a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), electron blocking layer (7), light emitting layer (3), hole blocking layer (8), electron transport layer (9) , The structure of the organic electroluminescent device in which the electron injection layer 10 and the cathode 4 are sequentially stacked is an example.

The organic electroluminescent device of the present application can be made of materials and methods known in the art, except that at least one layer of the organic material layer contains the compound of the present application, that is, the compound.

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 according to the present invention uses a physical vapor deposition (PVD) method, such as sputtering or e-beam evaporation, to deposit metal or conductive metal oxides or alloys thereof on a substrate It can be prepared by forming an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be made by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

In addition, the light emitting layer may be formed by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. The solution application method means, for example, spin coating, dip coating, doctor blading, screen printing, inkjet printing, spraying, roll coating, and the like, but is not limited to these.

In one embodiment of the present application, 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 positive electrode material is usually a material having a large work function to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as poly(3-methyl compound), poly[3,4-(ethylene-1,2-dioxy) compound] (PEDT), polypyrrole and polyaniline, but are not limited thereto.

The cathode material is preferably 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 is a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole-injecting material is a material capable of well injecting holes from the anode at a low voltage, and it is preferable that the high-occupied molecular orbital (HOMO) of the hole-injecting material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. Organic compounds, anthraquinones, and polyaniline-based conductive polymers of a poly compound, and the like, but are not limited thereto.

As the hole transport material, a material capable of receiving holes from an anode or a hole injection layer and transporting holes to a light emitting layer is suitable as a material having high mobility for holes. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.

As the electron transport material, a material capable of receiving electrons from the cathode well and transferring them to the light emitting layer, a material having high mobility for electrons is suitable. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.

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

The method of manufacturing the compound of Formula 1 and the production of the organic light emitting device using the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the invention, and the scope of the invention is not limited by them.

<Production Example>

Preparation Example 1

Synthesis of Intermediate 1-1

Under nitrogen, 10 g (40.65 mmol) of 4-bromo dibenzofuran, 5.1 g (20.32 mmol) of iodine and 6.6 g (20.32 mmol) of phenyl iodide diacetate, 150 ml acetic acid and 150 ml acetic acid The mixture was added to an anhydrous mixture solution, and 3 drops of sulfuric acid were added thereto, followed by stirring at room temperature for 10 hours. After completion of the reaction, ethyl acetate was added to the mixed solution, followed by washing with water, separating the layers, receiving only the organic layer, adding anhydrous magnesium sulfate, and stirring. After filtering the silica pad, the solution was concentrated under reduced pressure to purify the column, and the intermediate 1-1 was obtained in 65% yield.

Synthesis of Intermediate 1-2

Intermediate 1 9.8 g (26.35 mmol), carbazole 2.2 g (13.18 mmol), copper powder (2 g (32.53 mmol)) and potassium carbonate 3.6 g (26.35 mmol) in 70 ml dimethyl acetoamide, 24 at 130 °C Stir for hours. After completion of the reaction, after cooling to room temperature, the silica pad was filtered to remove copper powder, and the obtained solution was washed with water, and then only an organic layer was received and anhydrous magnesium sulfate was added and stirred. After filtering the silica pad, the solution was concentrated under reduced pressure to purify the column, and the intermediate 1-2 was obtained in 78% yield.

Synthesis of Compound 1

Intermediate 1-2 8.4 g (20.43 mmol), dibenzo[b,d]furan-4-ylboronic acid 4.76 g (22.47 mmol) and 2 mol% tetrakistriphenylphosphine (palladium) tetrahydro Put into 50 ml of furan and dissolve 40.86 mmol of potassium carbonate in 25 ml of water. After stirring at 80°C for 12 hours, the reaction was terminated and cooled to room temperature to separate water and organic layers. Anhydrous magnesium sulfate was added to the organic layer, followed by stirring. After filtering the silica pad, the solution was concentrated under reduced pressure to purify the column, and Compound 1 was obtained in 60% yield.

MS: [M+H] ⁺ = 500

3 is MS data of Compound 1.

Preparation Example 2

Synthesis of Compound 2

Intermediate 1-2 8.4 g (20.43 mmol) and dibenzo[b,d]furan-4-ylboronic acid instead of dibenzo[b,d]furan-1-ylboronic acid 4.76g (22.47mmol) except the above compound Reaction and purification were carried out in the same manner as in the synthesis of 1 to obtain compound 2 in a yield of 57%.

MS: [M+H] ⁺ = 500

Preparation Example 3

Synthesis of Compound 3

Intermediate 1-2 8.4 g (20.43 mmol) and dibenzo[b,d]furan-4-ylboronic acid instead of dibenzo[b,d]thiophen-4-ylboronic acid5.12g(22.47mmol) except for Reaction and purification were carried out in the same manner as in the synthesis of Compound 1 to obtain Compound 3 in a yield of 62%.

MS: [M+H] ⁺ = 516

Preparation Example 4

Synthesis of Intermediate 4-1

Intermediate 1-2 5 g (12.16 mmol), bis (pinacolato) diboron 3.7 g (14.59 mmol), potassium acetate 2.39 g (24.32 mmol), bis (dibenzylideneacetone) palladium (Bis(dibenzylideneacetone)palladium) 4mol% and tricyclohexylphosphine 0.27g (0.97mmol) was added to 50ml dioxane and stirred at 100°C for 12 hours. After completion of the reaction, the mixture was cooled to room temperature, added with anhydrous magnesium sulfate, stirred, filtered through a silica pad, and concentrated under reduced pressure. Column purification gave Intermediate 4-1 in 85% yield.

Synthesis of Compound 4

The reaction was performed in the same manner as in the synthesis of Compound 1, except that 4.75 g (10.34 mmol) of Intermediate 4-1 and 4.25 g (10.34 mmol) of Intermediate 1-2 were used instead of dibenzo[b,d]furan-4-ylboronic acid. Purification gave compound 4 in 70% yield.

MS: [M+H] ⁺ = 665

4 is MS data of compound 4.

Preparation Example 5

Synthesis of Intermediate 5-1

Intermediate 1-1 5 g (13.45 mmol) and 4.47 g (13.45 mmol, Cas No. 1247053-55-9) of 5-phenyl-5,12-dihydroindolo[3,2-a]carbazole instead of carbazole Reaction and purification were carried out in the same manner as in the synthesis of Intermediate 1-2 except for the use to obtain Intermediate 5-1 in 51% yield.

Synthesis of Compound 5

Reaction and purification in the same manner as in the synthesis of Compound 1 except for using Intermediate 5-1 4g (6.94mmol), Dibenzo[b,d]furan-4-ylboronic acid 1.62g (7.63mmol) instead of Intermediate 1-2 This gave compound 5 in 64% yield.

MS: [M+H] ⁺ = 665

Preparation Example 6

Synthesis of Compound 6

Intermediate 5-1 4g (6.94mmol), dibenzo[b,d]furan-1-ylboronic acid 1.62g (7.63mmol), except that the reaction and purification in the same manner as in the synthesis of Compound 1 to purify Compound 6 60 % Yield.

MS: [M+H] ⁺ = 665

Preparation Example 7

Synthesis of Intermediate 7-1

Intermediate 1-1 5g (13.45mmol), 5-(naphthalen-2-yl)-5,12-dihydroindolo[3,2-a]carbazole 5.14g (13.45mmol), except that the intermediate 1 Reaction and purification were carried out in the same manner as in the synthesis of -2 to obtain Intermediate 7-1 in 57% yield.

Synthesis of Compound 7

Compound 7 was reacted and purified in the same manner as in the synthesis of Compound 1, except that 4.8 g (7.67 mmol) of Intermediate 7-1 and 1.92 g (8.44 mmol) of dibenzo[b,d]thiophene-4-ylboronic acid were used. Was obtained in 60% yield.

MS: [M+H] ⁺ = 731

Preparation Example 8

Synthesis of Intermediate 8-1

Dibenzo[b,d]furan-2-ylboronic acid 10g (47.16mmol) and 1-bromo-2-nitrobenzene 9.48g (47.16mmol) was used for reaction and purification in the same manner as in the synthesis of Compound 1 To give Intermediate 8-1 in 78% yield.

Synthesis of Compound 8-2

10.6 g (36.78 mmol) of intermediate 8-1 and 90 ml of triethyl phosphite were added and stirred at reflux. After stirring for 10 hours, the mixture was cooled to room temperature, and then concentrated under reduced pressure. After washing with water, the mixture was extracted with ethyl acetate, the organic layer was taken out, anhydrous magnesium sulfate was added, stirred, filtered through a silica pad, and concentrated under reduced pressure. Column purification gave intermediate 8-2 in 66% yield.

Synthesis of Compound 8-3

Intermediate 8-2 6.24 g (24.27 mmol) of intermediate 8 and 9.02 g (24.27 mmol) of intermediate 1-1 were reacted and purified in the same manner as the synthesis of intermediate 1-2 to obtain intermediate 8-3 in 55% yield. Did.

Synthesis of Compound 8

Compound 8 was reacted and purified in the same manner as in the synthesis of Compound 1, except that 6.69 g (13.35 mmol) of Intermediate 8-3 and 3.12 g (14.69 mmol) of dibenzo[b,d]furan-4-ylboronic acid were used. Obtained in 72% yield.

MS: [M+H] ⁺ = 590

Preparation Example 9

Synthesis of Intermediate 9-1

Under nitrogen, 10 g (38.17 mmol) of 4-bromo dibenzothiophene, 4.8 g (19.08 mmol) of iodine and 6.1 g (19.08 mmol) of phenyl iodide diacetate were mixed with 130 ml acetic acid and 150 ml acetic acid. The mixture was added to an anhydrous mixture solution, and 3 drops of sulfuric acid were added thereto, followed by stirring at room temperature for 10 hours. After completion of the reaction, ethyl acetate was added to the mixed solution, followed by washing with water, separating the layers, receiving only the organic layer, adding anhydrous magnesium sulfate, and stirring. After filtration of silica pad, the solution was concentrated under reduced pressure to purify the column, and intermediate 9-1 was obtained in 53% yield.

Synthesis of Intermediate 9-2

Intermediate 9-1 7.8 g (20.11 mmol), carbazole 3.4 g (20.11 mmol), copper powder (1.8 g (30.16 mmol)) and potassium carbonate 2.8 g (20.11 mmol) in 60 ml dimethyl acetoamide and 130° Stir at C for 24 hours. After completion of the reaction, after cooling to room temperature, the silica pad was filtered to remove copper powder, and the obtained solution was washed with water, and then only an organic layer was received and anhydrous magnesium sulfate was added and stirred. After filtering the silica pad, the solution was concentrated under reduced pressure to purify the column, and the intermediate 9-2 was obtained in 66% yield.

Synthesis of Compound 9

5.7 g (13.34 mmol) of intermediate 9-2, 3.1 g (14.67 mmol) of dibenzo[b,d]furan-4-ylboronic acid and 2 mol% of tetrakistriphenylphosphine (palladium) tetrahydro Put into 50 ml of furan and dissolve 40.02 mmol of potassium carbonate in 25 ml of water. After stirring at 80°C for 12 hours, the reaction was terminated and cooled to room temperature to separate water and organic layers. Anhydrous magnesium sulfate was added to the organic layer, followed by stirring. After filtering the silica pad, the solution was concentrated under reduced pressure to purify the column, and compound 9 was obtained in a yield of 4.3 g and 62%.

MS: [M+H] ⁺ = 516

Preparation Example 10

Synthesis of Intermediate 10-1

Intermediate 9-1 was reacted and purified in the same manner as in the synthesis of Intermediate 9-2 except that 10g (25.78mmol) of Intermediate 9-1 and 4.9g (25.78mmol) of 9H-carbazole-3-carbonitrile were used to prepare Intermediate 10-1. % Yield.

Synthesis of Compound 10

Intermediate 10-1 6.5 (14.38mmol), except that dibenzo[b,d]furan-4-ylboronic acid was used, was reacted and purified in the same manner as in the synthesis of Compound 9 to obtain Compound 10 in 72% yield.

MS: [M+H] ⁺ = 541

5 is MS data of compound 10.

<Example>

A glass substrate coated with a thin film of ITO (ndium tin oxide) at a thickness of 1,000 에 was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer Co. was used as a detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and then transported to a plasma cleaner. In addition, after the substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum evaporator.

M-MTDATA (60 nm) / TCTA (80 nm) / host + 10% Ir(ppy) ₃ (300 nm)/ BCP (10 nm)/ Alq ₃ (30 nm) / LiF (1 nm) on the prepared ITO transparent electrode / Al (200nm) was configured in the order of the light emitting device, an organic EL device was manufactured using compound 1 as the host.

The structures of m-MTDATA, TCTA, Ir(ppy)3 and BCP are as follows.

<Experimental Example 1-2>

An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 2 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-3>

An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 3 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-4>

An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 4 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-5>

An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 5 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-6>

An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 6 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-7>

An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 7 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-8>

An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 8 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-9>

An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 9 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-10>

An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 10 was used instead of Compound 1 in Experimental Example 1-1.

<Comparative Example 1-1>

An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that GH 1 was used instead of Compound 1 in Experimental Example 1-1.

<Comparative Example 1-2>

An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that GH 2 was used instead of Compound 1 in Experimental Example 1-1.

<Comparative Example 1-3>

An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that GH 3 was used instead of Compound 1 in Experimental Example 1-1.

When current was applied to the organic light emitting devices manufactured by Experimental Examples 1-1 to 1-10 and Comparative Examples 1-1 and 1-3, the results in Table 1 were obtained.

compound
(Host) Voltage
(V@10mA/cm ² ) efficiency
(cd/A@10mA/cm ² ) EL peak
(nm) Experimental Example 1-1 Compound 1 3.63 44.93 517 Experimental Example 1-2 Compound 2 3.86 42.64 516 Experimental Example 1-3 Compound 3 3.85 43.62 518 Experimental Example 1-4 Compound 4 3.75 42.75 517 Experimental Example 1-5 Compound 5 3.88 42.51 515 Experimental Example 1-6 Compound 6 3.79 42.53 516 Experimental Example 1-7 Compound 7 3.77 44.52 516 Experimental Example 1-8 Compound 8 3.68 42.54 517 Experimental Example 1-9 Compound 9 3.88 42.58 518 Experimental Example 1-10 Compound 10 3.78 43.14 518 Comparative Example 1-1 GH 1 5.78 38.47 517 Comparative Example 1-2 GH 2 5.90 37.21 517 Comparative Example 1-3 GH 3 5.67 36.11 517

As a result of the experiment, the green organic EL devices of Experimental Examples 1-1 to 1-10 using the compounds represented by Compounds 1 to 10 according to the present invention as the host material of the light emitting layer are compared using the conventional compounds GH 1 to GH 3 It showed superior performance in terms of current efficiency and driving voltage than the green organic EL elements of Examples 1-1 to 1-3. In the case of compounds 1 to 10, a carbazole or a carbazole additional ring-condensed substituent at position 2 of dibenzofuran or dibenzothiophene is substituted, and dibenzofuran or dibenzothiophene at position 6 It is characterized by combining. In the case of GH1, carbazole and dibenzofuran are bonded to positions 2 and 8 of dibenzofuran, respectively, and GH2 is a compound in which two amine groups are additionally substituted by GH1.

GH3 is a compound in which carbazole binds at position 2 of dibenzofuran or dibenzothiophene, and dibenzofuran binds at positions 4 and 6.

Through the above table, it can be seen that this difference allows Experimental Examples 1-1 to 1-10 to have lower voltage and higher efficiency than Comparative Examples 1-1 to 1-3.

<Experimental Example 2-1>

An organic light-emitting diode in which Compound 1 was applied as a host of a light-emitting material layer was produced. First, a 40 mm x 40 mm x 0.5 mm thick ITO (including reflective plate) electrode attached glass substrate was subjected to ultrasonic cleaning for 5 minutes with isopropyl alcohol, acetone, and DI Water, and then dried in an oven at 100°C. After the substrate was cleaned, the plasma was treated with O ₂ for 2 minutes in vacuum and transferred to a deposition chamber to deposit other layers on top. The organic layer was deposited in the following order by evaporation from a heating boat under a vacuum of about 10 ^-7 Torr. At this time, the deposition rate of the organic material was set to 1 Å/s.

Hole injection layer (HIL; HAT-CN (Hexaazatriphenylenehexacarbonitrile), 70 Å), hole transport layer (HTL; NPB(N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)-benzidine) , 780 Å), electron blocking layer (EBL; mCBP(3,3-Di(9H-carbazol-9-yl)biphenyl), 150 Å), emitting layer (EML; using compound 1 as a host and delaying 4CzIPN 30% by weight doped with fluorescent material, 350 Å), hole blocking layer (HBL; B3PYMPM(4,6-Bis(3,5-di(pyridin-3-yl)phenyl)-2-methylpyrimidine); 100 Å), Electron transport layer (ETL: TPBi(2,2',2"-(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole)), 250 Å), electron injection layer (EIL; LiF , 8 Å), cathode (Al; 1000 Å).

After forming a capping layer with the CPL, it was encapsulated with glass. After the deposition of these layers, the film was transferred from the deposition chamber into a drying box and subsequently encapsulated using UV cured epoxy and a moisture getter.

<Experimental Example 2-2>

An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 2 was used instead of Compound 1 in Experimental Example 2-1.

<Experimental Example 2-3>

An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 3 was used instead of Compound 1 in Experimental Example 2-1.

<Experimental Example 2-4>

An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 4 was used instead of Compound 1 in Experimental Example 2-1.

<Experimental Example 2-5>

An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 5 was used instead of Compound 1 in Experimental Example 2-1.

<Experimental Example 2-6>

An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 6 was used instead of Compound 1 in Experimental Example 2-1.

<Experimental Example 2-7>

An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 7 was used instead of Compound 1 in Experimental Example 2-1.

<Experimental Example 2-8>

An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 8 was used instead of Compound 1 in Experimental Example 2-1.

<Experimental Example 2-9>

An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 9 was used instead of Compound 1 in Experimental Example 2-1.

<Experimental Example 2-10>

An organic light emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 10 was used instead of Compound 1 in Experimental Example 2-1.

<Comparative Example 2-1>

An organic light emitting diode was manufactured in the same manner as in Experimental Example 2-1, except that GH 4 (mCBP) was used instead of Compound 1 in Experimental Example 2-1.

compound
(Host) Voltage
(V@10mA/cm ² ) EQE
(%) CIE x CIE y Experimental Example 2-1 Compound 1 3.35 16.7 0.33 0.59 Experimental Example 2-2 Compound 2 3.35 16.3 0.33 0.59 Experimental Example 2-3 Compound 3 3.29 16.0 0.34 0.59 Experimental Example 2-4 Compound 4 3.33 16.8 0.34 0.58 Experimental Example 2-5 Compound 5 3.30 16.1 0.35 0.58 Experimental Example 2-6 Compound 6 3.37 15.9 0.34 0.59 Experimental Example 2-7 Compound 7 3.40 16.3 0.33 0.59 Experimental Example 2-8 Compound 8 3.38 16.6 0.34 0.58 Experimental Example 2-9 Compound 9 3.31 15.9 0.33 0.58 Experimental Example 2-10 Compound 10 3.28 16.0 0.33 0.59 Comparative Example 2-1 GH 4 (mCBP) 4.33 13.8 0.34 0.57

Examples 2-1 to 2-10 of the present invention use a compound in which heteroaryl groups containing three or more N, S, and O are sequentially bonded. On the other hand, compound GH 4 of Comparative Example 2-1 is a biphenyl group linking between carbazole and carbazole. When the organic compound synthesized according to the present invention is used as a host for a delayed fluorescent material layer, Comparative Example 2- The driving voltage was lowered and the external quantum efficiency (EQE) was improved compared to the case where the compound of 1 was used as the host of the light emitting material layer. As a result, it was confirmed that the organic compound of the present invention was applied to the organic light emitting layer to lower the driving voltage of the light emitting diode, improve the luminous efficiency, and improve the color purity. Therefore, by using the organic light emitting diode to which the organic compound of the present invention is applied, it can be utilized in light emitting devices such as organic light emitting diode display devices and/or lighting devices with reduced power consumption and improved luminous efficiency and device life.

1: Substrate
2: anode
3: light emitting layer
4: Cathode
5: hole injection layer
6: hole transport layer
7: Electronic blocking layer
8: hole blocking layer
9: electron transport layer
10: electron injection layer

Claims (16)

Compound represented by the formula (1):
[Formula 1]

In Chemical Formula 1,
X and Y are the same as or different from each other, and each independently O or S,
Z is N or CR,
R, R1 to R5, and R7 are the same as or different from each other, and each independently hydrogen; Nitrile group; heavy hydrogen; Halogen group; Carbonyl group; Ester groups; Imide group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthioxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkyl sulfoxy group; A substituted or unsubstituted aryl sulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may combine with an adjacent group to form a substituted or unsubstituted ring,
m and n are each independently an integer of 0 to 4, and when m is 2 or more, R1 is the same or different from each other, and when n is 2 or more, R4 is the same or different from each other,
o, p, q, and w are each independently an integer from 0 to 3, and when o is 2 or more, R2 is the same or different from each other, when p is 2 or more, R3 is the same or different from each other, and when q is 2 or more, R5 Is the same as or different from each other, and when w is 2 or more, R7 is the same as or different from each other. The method according to claim 1,
Chemical Formula 1 is a compound represented by the following Chemical Formula 2 or Chemical Formula 3:
[Formula 2]

[Formula 3]

In Formula 2 and Formula 3,
The definitions of X, Y, Z, R1 to R5, R7, m, n, o, p, q and w are as defined in Formula 1. The method according to claim 1,
Formula 1 is a compound represented by the following formula (4):
[Formula 4]

In Chemical Formula 4,
The definitions of Y, R1 to R5, R7, m, n, p, q and w are the same as those in Formula 1,
X ₁ is O or S,
X ₂ is O, S, CR'R'' or NR''',
The definitions of R', R'', R''' and R6 are the same as those of R, R1 to R5 and R7 in the formula (1),
r is an integer from 0 to 2, and when r is 2, R2 is the same as or different from each other,
s is an integer from 0 to 4, and when s is 2 or more, R6 is the same or different from each other. The method according to claim 1,
Chemical Formula 1 is a compound represented by the following Chemical Formula 2-1 or Chemical Formula 3-1:
[Formula 2-1]

[Formula 3-1]

In Chemical Formulas 2-1 and 3-1,
The definitions of Y, R1 to R5, m, n, p and q are the same as those in Formula 1,
X ₁ is O or S,
X ₂ is O, S, CR'R'' or NR''',
The definitions of R', R'', R''' and R6 are the same as those of R, R1 to R5 and R7 in the formula (1),
r is an integer from 0 to 2, and when r is 2, R2 is the same as or different from each other,
s is an integer from 0 to 4, and when s is 2 or more, R6 is the same or different from each other. The method according to claim 1,
Chemical Formula 1 is a compound represented by any one of the following Chemical Formulas 2-1-1 to 2-1-6:
[Formula 2-1-1]

[Formula 2-1-2]

[Formula 2-1-3]

[Formula 2-1-4]

[Formula 2-1-5]

[Formula 2-1-6]

In the above formula 2-1-1 to 2-1-6,
The definitions of Y, R1 to R5, m, n, p and q are the same as those in Formula 1,
X ₁ is O or S,
X ₂ is O, S, CR'R'' or NR''',
The definitions of R', R'', R''' and R6 are the same as those of R, R1 to R5 and R7 in the formula (1),
r is an integer from 0 to 2, and when r is 2, R2 is the same as or different from each other,
s is an integer from 0 to 4, and when s is 2 or more, R6 is the same or different from each other. The method according to claim 1,
Chemical Formula 1 is a compound represented by any one of the following Chemical Formulas 3-1-1 to 3-1-6:
[Formula 3-1-1]

[Formula 3-1-2]

[Formula 3-1-3]

[Formula 3-1-4]

[Formula 3-1-5]

[Formula 3-1-6]

In Chemical Formulas 3-1-1 to 3-1-6,
The definitions of Y, R1 to R5, m, n, p and q are the same as those in Formula 1,
X ₁ is O or S,
X ₂ is O, S, CR'R'' or NR''',
The definitions of R', R'', R''' and R6 are the same as those of R, R1 to R5 and R7 in the formula (1),
r is an integer from 0 to 2, and when r is 2, R2 is the same as or different from each other,
s is an integer from 0 to 4, and when s is 2 or more, R6 is the same or different from each other. The method according to claim 1,
R and R1 to R5 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or a compound that combines with adjacent groups to form a substituted or unsubstituted ring. The compound according to claim 1, wherein R is hydrogen. The method according to claim 1,
R1 to R5 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted carbazolyl group, or a compound that combines with an adjacent group to form a substituted or unsubstituted ring. The method according to claim 1, wherein Formula 1 is a compound represented by any one of the following structural formula:

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 layer of the organic material layer comprises the compound according to any one of claims 1 to 10. Light emitting element. The method according to claim 11,
The organic material layer includes a light emitting layer, the light emitting layer is an organic light emitting device comprising the compound of the formula (1). The method according to claim 12,
The light emitting layer is an organic light emitting device comprising the compound of Formula 1 as a phosphorescent host. The method according to claim 12,
The light-emitting layer is an organic light-emitting device comprising the compound of Formula 1 as a host, and a thermally activated delayed fluorescence compound as a dopant. The method according to claim 14, wherein the dopant comprises a thermally activated delayed fluorescent compound having a gap ((ΔE _st ) of 0.2 eV or less between the lowest excited triplet state (T ₁ ) and the lowest excited singlet state (S ₁ ). Organic light emitting device. The method according to claim 14, wherein the thermally activated delayed fluorescent compound is an organic light emitting device represented by any one of the following structural formula:

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