CN110785416B

CN110785416B - Compound and organic light emitting device comprising the same

Info

Publication number: CN110785416B
Application number: CN201880042006.1A
Authority: CN
Inventors: 尹洪植; 李俊烨; 柳志广; 洪玩杓; 金振珠
Original assignee: Sungkyunkwan University School Industry Cooperation; LG Chem Ltd
Current assignee: Sungkyunkwan University School Industry Cooperation; LG Chem Ltd
Priority date: 2017-11-03
Filing date: 2018-11-02
Publication date: 2023-05-19
Anticipated expiration: 2038-11-02
Also published as: KR102072923B1; CN110785416A; KR20190050711A

Abstract

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

Description

Compound and organic light emitting device comprising the same

Technical Field

The present application claims priority based on korean patent application No. 10-2017-0145960 filed on the date of 11 months in 2017 and korean patent application No. 10-2018-0132914 filed on the date of 11 months in 2018, which are all incorporated herein.

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

Background

In order to commercialize the organic light emitting device, it is necessary to improve the efficiency of the light emitting material, and for this reason, research on phosphorescence and delayed fluorescence materials is actively being conducted. However, in the case of the above-mentioned phosphorescent material, although high efficiency can be achieved, there is a problem in that the price of a metal complex necessary for achieving phosphorescence is high and the lifetime is short.

In the case of delayed fluorescent materials, a concept of thermally activated delayed fluorescence (TADF: thermally Activated Delayed Fluorescence) was recently introduced, and a high-efficiency green fluorescent material which is both a fluorescent material and has high external quantum efficiency was published. The concept of Thermally Activated Delayed Fluorescence (TADF) represents a phenomenon in which fluorescence emission is achieved by thermal activation causing reverse energy transfer from an excited triplet state to an excited singlet state, and is called delayed fluorescence from the viewpoint of generally generating long-life light emission due to light emission through a triplet path. The delayed fluorescent material can use either of fluorescent light emission and phosphorescent light emission, and thus can solve the problem of external quantum efficiency possessed by the existing fluorescent material, and can solve the problem of price of the phosphorescent material in terms that the metal complex may not be contained.

Disclosure of Invention

Technical problem

The present specification provides compounds and organic light emitting devices comprising the same.

Technical solution

The present specification provides a compound represented by the following chemical formula 1.

[ chemical formula 1]

In the above-mentioned chemical formula 1,

x1 is O or S, and the total number of the components is equal to or greater than zero,

ar1 and Ar2 are the same or different from each other and are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

r1 to R4 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amide 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 alkylthio group [ ]

Alkylthio), substituted or unsubstituted arylthio (++>

Aryl thio), substituted or unsubstituted alkylsulfonyl (++>

Alkylsulfoxy), substituted or unsubstituted arylsulfonyl (++>

Aryl sulfoxy), substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amine, substituted or unsubstituted Aryl phosphine, substituted or unsubstituted phosphine oxide, substituted or unsubstituted Aryl, or substituted or unsubstituted heteroaryl,

r1 is an integer of 1 to 6,

r2 and r3 are each an integer of 1 to 7,

r4 is an integer of 1 to 5,

when r1 to r4 are 2 or more, the structures in parentheses of 2 or more are the same or different from each other.

In addition, the present specification provides an organic light emitting device, including: the organic light-emitting device includes a first electrode, a second electrode provided opposite to the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contains the compound.

Effects of the invention

The organic light emitting device including the compound represented by chemical formula 1 according to an embodiment of the present specification can achieve an improvement in efficiency, a low driving voltage, and/or an improvement in lifetime characteristics.

Drawings

Fig. 1 illustrates an organic light emitting device according to an embodiment of the present specification.

Symbol description

10: organic light emitting device

20: substrate board

30: first electrode

40: light-emitting layer

50: second electrode

Detailed Description

The present specification will be described in more detail below.

The present specification provides a compound represented by the above chemical formula 1.

The compound represented by chemical formula 1 according to an embodiment of the present specification contains a triazinyl group functioning as an electron acceptor to facilitate electron injection, and an organic light emitting device including the same has characteristics of high efficiency and long lifetime.

In addition, in the compound represented by the above chemical formula 1, the triazine group functioning as an electron acceptor and the biscarbazole group functioning as an electron donor are separated with a linking group interposed therebetween, and thus the delayed fluorescence characteristic is enhanced, and the organic light emitting device using the same as a light emitting layer can improve the efficiency of the device.

According to an embodiment of the present specification, the compound represented by the above chemical formula 1 is a delayed fluorescence compound.

The number of excitons generated in the singlet and triplet states in a general organic light emitting device is generated at a ratio of 25:75 (singlet: triplet), and can be classified into fluorescence emission, phosphorescence emission, and thermally activated delayed fluorescence emission according to the light emission form according to the movement of the excitons. The phosphorescence emission means that excitons of a triplet excited state (excited state) transition to a Ground state to emit light, the fluorescence emission means that excitons of a singlet excited state (excited state) transition to a Ground state to emit light, and the thermally activated delayed fluorescence emission means that transition from the triplet excited state (excited state) to the singlet excited state (excited state) between the opposite systems is induced to cause fluorescence emission.

The thermally activated delayed fluorescence is distinguished from fluorescence in that the peak position of the emission spectrum is the same as that of fluorescence but the decay time (decay time) is long, and S is present in the peak position of the emission spectrum compared with that of phosphorescence although the decay time is long ₁ -T ₁ The difference in energy is distinguished from phosphorescence. At this time, S ₁ Is in a singlet (single) energy level, T ₁ Is a triplet energy level.

In the present specification, when a certain component is indicated as being "included" in a certain portion, unless otherwise stated, it means that other components may be further included, and not excluded.

In the present specification, examples of the substituents are described below, but are not limited thereto.

The term "substituted" as used herein means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" means a substituent substituted with 1 or 2 or more substituents selected from deuterium, halogen group, nitrile group, nitro group, imide group, amide group, carbonyl group, ester group, hydroxyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted alkylsulfonyl group, substituted or unsubstituted arylsulfonyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted silyl group, substituted or unsubstituted boron group, substituted or unsubstituted amino group, substituted or unsubstituted arylphosphine group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group, or a substituent bonded with 2 or more substituents among the above-exemplified substituents, or does not have any substituent. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.

In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 30. Specifically, the compound may have the following structure, but is not limited thereto.

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In the present specification, in the amide group, nitrogen of the amide group may be hydrogen; a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 30. Specifically, the compound may have the following structure, but is not limited thereto.

In the present specification, in the ester group, oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.

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

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

In the present specification, the above-mentioned alkoxy group may be a straight chain, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-neoxy, n-nonoxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like are possible, but not limited thereto.

In the present specification, the amine group may be selected from the group consisting of-NH ₂ The alkyl amine group, the N-alkylaryl amine group, the aryl amine group, the N-arylheteroaryl amine group, the N-alkylheteroaryl amine group and the heteroaryl amine group are not particularly limited, but are preferably 1 to 30 carbon atoms. Specific examples of the amine group include a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamine group, a naphthylamino group, a biphenylamino group, an anthracenylamino group, a 9-methylanthracenylamine group, a diphenylamino group, an N-phenylnaphthylamino group, a xylylamino group, an N-phenyltolylamino group, a triphenylamino group, an N-phenylbiphenylamino group, an N-phenylnaphthylamino group, an N-biphenylnaphthylamino group, an N-naphthylfluorenylamino group, an N-phenylphenanthrylamino group, an N-biphenylphenanthrenylamino group, an N-phenylfluorenylamino group, an N-biphenylfluorenylamino group, and the like, but are not limited thereto.

In the present specification, the N-alkylaryl amine group means an amine group in which an alkyl group and an aryl group are substituted on N of the amine group.

In the present specification, the N-arylheteroarylamino group means an amino group in which an aryl group and a heteroaryl group are substituted on N of the amino group.

In the present specification, the N-alkylheteroaryl amine group means an amine group in which an alkyl group and a heteroaryl group are substituted on N of the amine group.

In the present specification, the alkyl group in the alkylamino group, the N-arylalkylamino group, the alkylthio group, the alkylsulfonyl group, and the N-alkylheteroarylamino group is the same as the examples of the alkyl group described above. Specifically, the alkylthio group includes a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group, an octylthio group, and the like, and the alkylsulfonyl group includes a methanesulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, and the like, but is not limited thereto.

In the present specification, the alkenyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.

In the present specification, the alkynyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples thereof include, but are not limited to, ethynyl (ethyl), propynyl (propyl), butynyl (butyl), pentynyl (penyl), hexynyl (hexynyl), heptynyl (hepynyl), octynyl (octynyl), nonynyl (nonynyl), and the like.

In the present specification, 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.

In the present specification, the boron group may be-BR ₁₀₀ R ₁₀₁ R is as described above ₁₀₀ And R is ₁₀₁ And each may be, the same or different from each other, independently selected from hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

In the present specification, the phosphine oxide group specifically includes, but is not limited to, diphenyl phosphine oxide group, dinaphthyl phosphine oxide group, and the like.

In the present specification, the aryl group is not particularly limited, but an aryl group having 6 to 30 carbon atoms is preferable, and the aryl group may be a single ring or a multiple ring.

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

The number of carbon atoms in the case where the aryl group is a polycyclic aryl group is not particularly limited, but is preferably 10 to 30. Specifically, the polycyclic aryl group may be naphthyl, anthryl, phenanthryl, triphenyl, pyrenyl, phenalenyl, perylenyl,

A group, a fluorenyl group, a fluoranthenyl group, and the like, but is not limited thereto.

In the present specification, the above fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.

In the case where the above fluorenyl group is substituted, it may be,

etc. However, the present invention is not limited thereto.

In the present specification, an "adjacent" group refers to a substituent substituted on an atom directly bonded to an atom substituted with the substituent, a substituent closest to the substituent in steric structure, or another substituent substituted on an atom substituted with the substituent. For example, 2 substituents substituted at the ortho (ortho) position in the benzene ring and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups.

In the present specification, the aryl groups in the aryloxy group, the arylthio group, the arylsulfonyl group, the N-arylalkylamino group, the N-arylheteroarylamino group, and the arylphosphino group are the same as those exemplified above. Specifically, examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, a 3, 5-dimethylphenyloxy group, a 2,4, 6-trimethylphenoxy group, a p-tert-butylphenyloxy group, a 3-biphenylyloxy group, a 4-biphenylyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a 1-anthracenyloxy group, a 2-anthracenyloxy group, a 9-anthracenyloxy group, a 1-phenanthrenyloxy group, a 3-phenanthrenyloxy group, a 9-phenanthrenyloxy group, and the like, and examples of the arylthio group include a phenylthio group, a 2-methylphenylthio group, a 4-tert-butylphenylthio group, and the like, and examples of the arylsulfonyl group include a benzenesulfonyl group, a p-toluenesulfonyl group, and the like, but are not limited thereto.

In the present specification, as examples of the arylamine group, there are substituted or unsubstituted monoarylamine groups, or substituted or unsubstituted diarylamino groups. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing 2 or more of the above aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or both a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In this specification, a heteroaryl group contains one or more non-carbon atoms, i.e., heteroatoms, and specifically, the heteroatoms may contain one or more atoms selected from O, N, se and S. The number of carbon atoms is not particularly limited, but is preferably 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,

Azolyl, (-) -and (II) radicals>

Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo->

Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline (phenanthrinyl), iso>

Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.

In the present specification, as examples of the heteroarylamino group, there are a substituted or unsubstituted mono-heteroarylamino group, or a substituted or unsubstituted di-heteroarylamino group. Heteroaryl amine groups containing 2 or more of the above heteroaryl groups are heteroaryl groups which may contain a monocyclic heteroaryl group, a polycyclic heteroaryl group, or both a monocyclic heteroaryl group and a polycyclic heteroaryl group. For example, the heteroaryl group in the above heteroaryl amine group may be selected from the examples of heteroaryl groups described above.

In the present specification, examples of heteroaryl groups in the N-arylheteroarylamino group and the N-alkylheteroarylamino group are the same as those described above.

According to an embodiment of the present specification, in the above chemical formula 1, R1 to R4 are hydrogen.

According to an embodiment of the present specification, the above chemical formula 1 is represented by the following chemical formula 1-1.

[ chemical formula 1-1]

In the above-mentioned chemical formula 1-1,

the definitions of X1, ar1 and Ar2 are the same as those in the above chemical formula 1.

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

[ chemical formulas 1-2]

[ chemical formulas 1-3]

In the above chemical formulas 1-2 and 1-3,

According to an embodiment of the present specification, in the above chemical formula 1, ar1 and Ar2 are the same or different from each other, and each is independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

According to an embodiment of the present specification, in the above chemical formula 1, ar1 and Ar2 are the same or different from each other, and each is independently an aryl group substituted or unsubstituted with an alkyl group, or a heteroaryl group substituted or unsubstituted with an aryl group.

According to an embodiment of the present specification, in the above chemical formula 1, ar1 and Ar2 are the same or different from each other, and each is independently a phenyl group, a biphenyl group, a fluorenyl group substituted or unsubstituted with an alkyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group substituted or unsubstituted with an aryl group.

According to an embodiment of the present specification, in the above chemical formula 1, ar1 and Ar2 are the same or different from each other, and each is independently a phenyl group, a biphenyl group, a fluorenyl group substituted or unsubstituted with a methyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present specification, the above chemical formula 1 is selected from the following compounds.

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According to an embodiment of the present specification, the triplet (triplet) level of the compound represented by the above chemical formula 1 may be 2.1eV or more, preferably 2.1eV or more and 3.0eV or less, 2.2e V or more and 3.0eV or less, and 2.4eV or more and 2.9eV. When the triplet (triplet) level of the compound represented by the above chemical formula 1 satisfies the above range, electron injection becomes easy and the formation ratio of excitons increases, so that there is an advantage of improving light emission efficiency.

According to an embodiment of the present specification, Δe of the compound represented by the above chemical formula 1 _st Is not less than 0eV and not more than 0.3eV, preferably not less than 0eV and not more than 0.2 eV. When the difference between the singlet (single) and triplet (triplet) levels of the compound represented by the above chemical formula 1 satisfies the above range, excitons generated in the triplet state decrease the time in which the excitons stay in the triplet state by increasing the rate and speed at which the reverse intersystem crossing (RISC) moves to the singlet state, and thus have an advantage of increasing the efficiency and lifetime of the organic light emitting device.

According to an embodiment of the present specification, Δe of the compound represented by the above chemical formula 1 _st Less than 0.2eV. Here Δe _st Refers to the singlet energy level (S) of the compound represented by chemical formula 1 ₁ ) And triplet energy level (T) ₁ ) And (3) a difference.

Delta E when the Compound represented by the above chemical formula 1 _st Less than 0.2eV, triplet-to-singlet crossover effectively occurs with the effect of improving the external light-emitting efficiency and lifetime of the device, when ΔE _st If the value is 0.2eV or more, triplet-to-singlet crossover is less likely to occur, leading to a problem of reduced efficiency and lifetime.

According to an embodiment of the present specification, there is provided an organic light emitting device including: the organic light-emitting device includes a first electrode, a second electrode provided opposite to the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contains a compound represented by chemical formula 1 of the present application.

According to an embodiment of the present specification, the organic layer of the organic light emitting device of the present specification may be formed of a single-layer structure, or may be formed of a multilayer structure in which two or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto, and may include fewer or more organic layers.

For example, the structure of the organic light emitting device of the present specification may have the structure shown in fig. 1, but is not limited thereto.

Fig. 1 illustrates a structure of an organic light emitting device 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20. Fig. 1 is an exemplary structure of an organic light emitting device according to an embodiment of the present specification, and may further include other organic layers.

According to an embodiment of the present specification, the organic layer includes a light emitting layer including a compound represented by chemical formula 1 of the present application.

According to an embodiment of the present specification, the organic layer includes a light emitting layer including a compound represented by chemical formula 1 of the present application as a dopant of the light emitting layer.

According to an embodiment of the present invention, the light-emitting substance of the light-emitting layer is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, the light-emitting layer contains a compound represented by chemical formula 1 of the present application as a dopant of the light-emitting layer, and contains an organic compound as a host, at least either of the excited singlet energy and the excited triplet energy having a value higher than that of a light-emitting material of the compound, having hole-transporting ability, electron-transporting ability, and preventing a long wavelength of light emission, and an organic compound having a high glass transition temperature.

According to one embodiment of the present disclosure, the organic layer includes a light-emitting layer, and the light-emitting layer includes a host.

According to an embodiment of the present disclosure, the organic layer includes a light-emitting layer including one or more selected from an aromatic condensed ring derivative and a heterocyclic compound as a main body of the light-emitting layer.

According to an embodiment of the present specification, the aromatic condensed ring derivative includes anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic compound includes carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds

Pyrimidine derivatives, and the like, but are not limited thereto.

According to an embodiment of the present specification, the body may include any one or more selected from the following compounds, but is not limited thereto.

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According to an embodiment of the present disclosure, the organic layer includes a light-emitting layer including a compound represented by chemical formula 1 of the present application as a dopant of the light-emitting layer, and includes one or more selected from an aromatic condensed ring derivative and a heterocyclic compound as a host of the light-emitting layer.

According to an embodiment of the present disclosure, the light emitting layer includes the dopant and the host in a weight ratio of 1:99 to 50:50.

According to an embodiment of the present disclosure, the organic layer includes a light-emitting layer including a dopant including a compound represented by chemical formula 1 of the present application and a host including any one or more selected from the aromatic condensed ring derivatives and heterocyclic compounds at a weight ratio of 1:99 to 50:50.

According to an embodiment of the present disclosure, the organic layer includes a light emitting layer, and the light emitting layer may further include a fluorescent emitter (emitter).

When the fluorescent emitter is contained in the light emitting layer, the fluorescent emitter and the host are contained in a weight ratio of 0.5:99.5 to 10:90.

As the fluorescent emitter in the present specification, an anthracene compound, a pyrene compound, a boron compound, or the like can be used, but the present invention is not limited thereto.

In the organic light-emitting device of the present specification, the dopant that is included in the light-emitting layer includes the compound of the present specification, that is, the compound represented by the chemical formula 1, and the host that is included in the light-emitting layer includes not less than one selected from the aromatic condensed ring derivative and the heterocyclic compound described above, and can be manufactured by a material and a method known in the art.

In the case where the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, it can be manufactured as follows: a first electrode is formed by vapor deposition of a metal or a metal oxide having conductivity or an alloy thereof on a substrate by a physical vapor deposition method (PVD: physical Vapor Deposition) such as a sputtering method (sp uttering) or an electron beam evaporation method (e-beam evaporation), then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the first electrode, and then a substance usable as a second electrode is vapor deposited on the organic layer. In addition to this method, the second electrode material, the organic layer, and the first electrode material may be sequentially deposited on the substrate to manufacture an organic light-emitting device. In addition, the heterocyclic compound represented by the above chemical formula 1 may be used not only in the vacuum deposition method but also in the solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.

According to an embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode.

According to another embodiment of the present specification, the first electrode is a cathode, and the second electrode is an anode.

As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, and the like, or alloys thereof; metal oxides such as zinc oxide, indium tin oxide (ito), and Indium Zinc Oxide (IZO); such as ZnO, al or SnO ₂ A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.

As the cathode material, a material having a small work function is generally preferred in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, and the likeA metal or an alloy thereof; such as LiF/Al or LiO ₂ And multi-layer structural materials such as Al and Mg/Ag, but not limited thereto.

The hole injection layer is a layer that injects holes from an electrode, and the following compounds are preferable as the hole injection substance: the light-emitting device has a hole transporting capability, a hole injecting effect from an anode, an excellent hole injecting effect for a light-emitting layer or a light-emitting material, prevention of migration of excitons generated in the light-emitting layer to the electron injecting layer or the electron injecting material, and an excellent thin film forming capability. The HOMO (highest occupied molecular orbital ) of the hole-injecting substance is preferably between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophenes, arylamine-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene (perylene) -based organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers.

The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer, and as a hole-transporting substance, a substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer, a substance having a large mobility to the holes is preferable. Specific examples thereof include an arylamine-based organic substance, a conductive polymer, and a block copolymer having both conjugated and unconjugated portions, but are not limited thereto.

The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and as an electron transporting substance, a substance that can well inject electrons from the cathode and transfer the electrons to the light emitting layer is suitable for a substance having a large mobility of electrons. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq ₃ But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The electron transport layer may be used with any desired cathode material as used in the art. In particular, examples of suitable cathode materials are those havingTypical substances having a low work function and accompanied by an aluminum or silver layer, in particular cesium, barium, calcium, ytterbium and samarium, are in each case accompanied by an aluminum or silver layer.

The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound as follows: has an electron transporting ability, an electron injecting effect from a cathode, an excellent electron injecting effect to a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from migrating to a hole injecting layer, and has an excellent thin film forming ability. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,

Azole,/->

Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.

Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).

The organic light emitting device according to the present specification may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.

Modes for carrying out the invention

In the following, examples are described in detail for the purpose of specifically explaining the present specification. However, the embodiments according to the present specification may be modified into various forms, and the scope of the present specification should not be construed as being limited to the embodiments described in detail below. The embodiments of the present description are provided to more fully explain the present description to those skilled in the art.

< production example >

The process for the preparation of the materials of the present invention is shown below, starting from the reaction of synthesis of dibenzofurans or dibenzothiophenes substituted with bromine and chlorine. Specific examples of compounds are synthesized by introducing triazinyl and dicarbazole into dibenzofuran substituted with bromine and chlorine or dibenzothiophene substituted with fluorine and chlorine.

< production example 1-1> Synthesis of Compound 1-A

[ reaction type 1-1]

30g (89.5 mmol) of 2-bromo-1-chloro-4-fluoro-3-iodobenzene, (2-hydroxyphenyl) boronic acid 90mmol, 200mL of tetrahydrofuran and 100mL of water were mixed and heated to 60 ℃. To this was added 268.5mmol of potassium carbonate and 1mmol of palladium tetraphenylphosphine, and the mixture was stirred in a reflux state for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then distilled. Purification by column chromatography using chloroform/hexane gave 21.6g of compound 1-a (yield 80%).

MS[M+H]+＝301

< production example 1-2> Synthesis of Compound 1-B

[ reaction type 1-2]

30g (89.5 mmol) of 1-bromo-4-chloro-3-fluoro-2-iodobenzene, 90mmol of phenylthiol, 200mL of tetrahydrofuran and 100mL of water were mixed and heated to 60 ℃. To this was added 268.5mmol of potassium carbonate and 1mmol of palladium tetraphenylphosphine, and the mixture was stirred in a reflux state for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then distilled. Purification by column chromatography using chloroform/hexane gave 22.8g of compound 1-B (yield 70%).

MS[M+H]+＝364

< production example 2-1> Synthesis of Compound 2-A

[ reaction type 2-1]

20g (66.3 mmol) of Compound 1-A, 200mL of dimethylformamide and 133mmol of potassium carbonate were mixed and heated at 100℃for 5 hours. After the reaction, the reaction solution which returns to the room temperature is reversely precipitated in water

reverse precipitation) to give a solid, and the obtained solid was purified by column chromatography using chloroform/hexane to give 17.7g of compound 2-A (yield 95%).

MS[M+H]+＝281

< production example 2-2> Synthesis of Compound 2-B

[ reaction type 2-2]

20g (54.8 mmol) of Compound 1-B, 200mL of dimethylformamide, 110mmol of potassium carbonate and 2mmol% of palladium acetate were mixed and stirred at reflux for 6 hours. After the reaction, the reaction solution was subjected to reverse precipitation in water to obtain a solid, and the obtained solid was purified by column chromatography using chloroform/hexane to obtain 9.7g of Compound 2-B (yield: 75%).

MS[M+H]+＝236

< production example 3-1> Synthesis of Compound 3-A

[ reaction type 3-1]

10g (35.5 mmol) of compound 2-A, 9-phenyl-9H, 9'H-3,3' -biscarbazole, 35.5mmol, toluene 100mL and 53.3mmol of sodium tert-butoxide were mixed and heated to 100deg.C. To this was added 1mmol% of tetrakis triphenylphosphine palladium, and stirred in a reflux state for 3 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was distilled to obtain a solid. The obtained solid was purified by column chromatography using chloroform/hexane to obtain 19.8g of compound 3-a (yield 92%).

MS[M+H]+＝609

< production example 3-2> Synthesis of Compound 3-B

[ reaction type 3-2]

10g (35.5 mmol) of compound 2-A, 9-phenyl-9H, 9'H-2,3' -biscarbazole, 35.5mmol, toluene 100mL and 53.3mmol of sodium tert-butoxide were mixed and heated to 100deg.C. To this was added 1mmol% of tetrakis triphenylphosphine palladium, and stirred in a reflux state for 3 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was distilled to obtain a solid. The obtained solid was purified by column chromatography using chloroform/hexane to obtain 20.1g of compound 3-B (yield 93%).

MS[M+H]+＝609

< production example 3-3> Synthesis of Compound 3-C

[ reaction type 3-3]

10g (42.2 mmol) of compound 2-B, 9-phenyl-9H, 9'H-3,3' -biscarbazole 42.2mmol, toluene 100mL and sodium tert-butoxide 63.3mmol were mixed and heated to 100deg.C. To this was added 1mmol% of tetrakis triphenylphosphine palladium, and stirred in a reflux state for 3 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was distilled to obtain a solid. The obtained solid was purified by column chromatography using chloroform/hexane to obtain 23.7g of compound 3-C (yield 90%).

MS[M+H]+＝625

< production example 4-1> Synthesis of Compound 4-A

[ reaction type 4-1]

10g (16.4 mmol) of compound 3-A, 16.4mmol of bis (pinacolato) diboron, 49.2mmol of potassium acetate and 1, 4-di

Alkane 100mL was mixed and heated to 100 ℃. To this was added 1mmol% palladium acetate and stirred at reflux for 12 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was distilled to obtain a solid. The obtained solid was purified by column chromatography using chloroform/hexane to obtain 10g of compound 4-a (yield 87%).

MS[M+H]+＝701

< production example 4-2> Synthesis of Compound 4-B

[ reaction type 4-2]

10g (16.4 mmol) of compound 3-B, 16.4mmol of bis (pinacolato) diboron, 49.2mmol of potassium acetate and 1, 4-di

Alkane 100mL was mixed and heated to 100 ℃. To this was added 1mmol% palladium acetate and stirred at reflux for 12 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was distilled to obtain a solid. The obtained solid was purified by column chromatography using chloroform/hexane to obtain 9.8g of compound 4-B (yield 85%).

MS[M+H]+＝701

< production example 4-3> Synthesis of Compound 4-C

[ reaction type 4-3]

10g (16 mmol) of compound 3-C, 16mmol of bis (pinacolato) diboron, 48mmol of potassium acetate and 1, 4-di

Alkane 100mL was mixed and heated to 100 ℃. To this was added 1mmol% palladium acetate and stirred at reflux for 12 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was distilled to obtain a solid. The obtained solid was purified by column chromatography using chloroform/hexane to obtain 9.7g of compound 4-C (yield 85%).

MS[M+H]+＝717

< production example 5-1> Synthesis of Compound 1

[ reaction type 5-1]

5g (7.1 mmol) of compound 4-A, 7.1mmol of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine, 50mL of tetrahydrofuran and 25mL of water were mixed and heated to 60 ℃. 21.3mmol of potassium carbonate and 1mmol of palladium tetraphenylphosphine were added thereto, and stirred in a reflux state for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then distilled. Purification by column chromatography using chloroform/hexane gave 5.1g of compound 1 (yield 90%).

MS[M+H]+＝806

< production example 5-2> Synthesis of Compound 2

[ reaction type 5-2]

5g (7.1 mmol) of the compound 4-A, 2- ([ 1,1' -biphenyl ] -3-yl) -4-chloro-6-phenyl-1, 3, 5-triazine 7.1mmol, 50mL of tetrahydrofuran and 25mL of water are mixed and heated to 60 ℃. 21.3mmol of potassium carbonate and 1mmol of palladium tetraphenylphosphine were added thereto, and stirred in a reflux state for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then distilled. Purification by column chromatography using chloroform/hexane gave 5.5g of compound 2 (yield 88%).

MS[M+H]+＝882

< production example 5-3> Synthesis of Compound 3

[ reaction type 5-3]

5g (7.1 mmol) of compound 4-B, 7.1mmol of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine, 50mL of tetrahydrofuran and 25mL of water were mixed and heated to 60 ℃. 21.3mmol of potassium carbonate and 1mmol of palladium tetraphenylphosphine were added thereto, and stirred in a reflux state for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then distilled. Purification by column chromatography using chloroform/hexane gave 5.2g of compound 3 (yield 91%).

MS[M+H]+＝806

< production example 5-4> Synthesis of Compound 4

[ reaction type 5-4]

5.1g (7.1 mmol) of the compound 4-C, 2-chloro-4, 6-diphenyl-1, 3, 5-triazine 7.1mmol, 50mL of tetrahydrofuran and 25mL of water were mixed and heated to 60 ℃. 21.3mmol of potassium carbonate and 1mmol of palladium tetraphenylphosphine were added thereto, and stirred in a reflux state for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then distilled. Purification by column chromatography using chloroform/hexane gave 5.2g of compound 4 (yield 90%).

MS[M+H]+＝822

< production example 5-5> Synthesis of Compound 5

[ reaction type 5-5]

In the above preparation example 5-4, except that 7.1mmol of 2- ([ 1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine was used instead of 7.1mmol of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine, the same procedure was followed to obtain 5.6g of compound 5 (yield 88%).

MS[M+H]+＝898

< production example 5-6> Synthesis of Compound 6

[ reaction type 5-6]

In the above production example 5-2, except that 7.1mmol of 2-chloro-4- (dibenzo [ b, d ] furan-4-yl) -6-phenyl-1, 3, 5-triazine was used instead of 7.1mmol of 2- ([ 1,1' -biphenyl ] -3-yl) -4-chloro-6-phenyl-1, 3, 5-triazine, 5.4g of compound 6 was obtained (yield 85%) by the same method.

MS[M+H]+＝896

< production example 5-7> Synthesis of Compound 7

[ reaction type 5-7]

5.1g (7.1 mmol) of the compound 4-C, 2-chloro-4- (dibenzo [ b, d ] thiophen-2-yl) -6-phenyl-1, 3, 5-triazine 7.1mmol, 50mL of tetrahydrofuran and 25mL of water are mixed and heated to 60 ℃. 21.3mmol of potassium carbonate and 1mmol of palladium tetraphenylphosphine were added thereto, and stirred in a reflux state for 3 hours. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature, and then distilled. Purification by column chromatography using chloroform/hexane gave 5.7g of compound 7 (yield 87%).

MS[M+H]+＝928

< production example 5-8> Synthesis of Compound 8

[ reaction type 5-8]

In the above production example 5-2, except that 7.1mmol of 3- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -9-phenyl-9H-carbazole was used instead of 7.1mmol of 2- ([ 1,1' -biphenyl ] -3-yl) -4-chloro-6-phenyl-1, 3, 5-triazine, the production was performed in the same manner, whereby 5.7g of compound 8 was obtained (yield 83%).

MS[M+H]+＝971

< production example 5-9> Synthesis of Compound 9

[ reaction type 5-9]

In the above production example 5-2, the same procedure was repeated except for using 7.1mmol of 2-chloro-4- (9, 9-dimethyl-9H-fluoren-2-yl) -6-phenyl-1, 3, 5-triazine instead of 7.1mmol of 2- ([ 1,1' -biphenyl ] -3-yl) -4-chloro-6-phenyl-1, 3, 5-triazine, whereby 5.4g of compound 9 was obtained (yield 82%).

MS[M+H]+＝922

The substance in the specific example is synthesized by introducing a plurality of dicarbazole and triazine species by the same reaction as the above reaction scheme.

< example >

Example 1

In this example, the compound represented by chemical formula 1 according to one embodiment of the present specification was included in a light-emitting layer together with a host material (m-CBP) having a triplet state value of 2.5eV or more, to manufacture an organic light-emitting device, and characteristics were evaluated.

To ITO (indium tin oxide)

Thickness of (2)The glass substrate coated with the thin film was put into distilled water in which a detergent was dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, it was subjected to ultrasonic washing with distilled water twice for 10 minutes. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine. On the ITO transparent electrode thus prepared, each thin film was vacuum-deposited by vacuum deposition to a vacuum degree of 5.0X10 ^-4 Pa is laminated. First, add ∈>

Is thermally vacuum evaporated to form a hole injection layer.

Vacuum evaporating the following compound 4-4' -bis [ N- (1-naphthyl) -N-phenylamino ] as a hole transporting substance on the hole injection layer]Biphenyl (NPB)

And a hole transport layer is formed.

Film thickness on the hole transport layer

Vacuum evaporation of the following compound N- ([ 1,1' -biphenyl)]-4-yl) -N- (4- (11- ([ 1,1' -biphenyl)]-4-yl]-11H-benzo [ a ]]Carbazol-5-yl) phenyl) - [1,1' -biphenyl]-4-amine (EB 1)/(b 1)>

And an electron blocking layer is formed.

Then, the electron blocking layer is coated with a film thickness

Will be as followsThe m-CBP and the compound 1 were vacuum-evaporated at a weight ratio of 70:30 to form a light-emitting layer.

Film thickness on the light-emitting layer

The compound HB1 was vacuum-deposited to form a hole blocking layer.

Vacuum vapor deposition was performed on the hole blocking layer to obtain a mixture of the compound ET1 and the compound LiQ (Lithium Quinolate, 8-hydroxyquinoline lithium) at a weight ratio of 1:1

The thickness of (2) forms the electron injection and transport layer. Lithium fluoride (LiF) is sequentially added to the electron injection and transport layer>

Is made of aluminum +. >

And the thickness of the metal layer is evaporated to form a cathode.

In the above process, the vapor deposition rate of the organic matter is maintained

Lithium fluoride maintenance of cathode

Is kept at>

Is to maintain a vacuum degree of 2X 10 during vapor deposition ^-7 ～5×10 ^-6 The support is thus fabricated into an organic light emitting device. />

Examples 2 to 9

An organic light emitting device was fabricated in the same manner as in example 1, except that the compound of table 1 below was used instead of the compound 1 in example 1.

Comparative examples 1 to 5

An organic light emitting device was fabricated in the same manner as in example 1, except that the following compounds T1 to T4 and 4CzIPN were used instead of compound 1 in example 1.

When a current was applied to the organic light emitting devices fabricated by examples 1 to 9 and comparative examples 1 to 5, the following [ table 1] results were obtained.

TABLE 1

As shown in table 1, the devices of examples 1 to 9 using the compound of the structure of chemical formula 1 as a parent core all obtained results of low voltage and improved efficiency as compared with the device of comparative example 5 using the substance of the compound 4 CzIPN. Further, by comparing the devices of comparative examples 1 to 4 with the present examples, it was found that the characteristics of the structures of the present examples in terms of voltage and efficiency were improved as compared with the compounds (T3 and T4) in which the triazinyl group and the carbazolyl group are bonded at the meta (meta) position on the benzene ring of dibenzofuran and the compounds (T1 and T2) in which the triazinyl group is not bonded to dibenzofuran or dibenzothiophene. As shown in the above table 1, it was confirmed that the compound according to the present invention was excellent in light-emitting ability and high in color purity, and thus, was applicable to a delayed fluorescence organic light-emitting device.

Experimental example

In the case of HOMO and LUMO (lowest unoccupied molecular orbital ), the measurement compound was dissolved in Dimethylformamide (DMF) at a concentration of 5mM and an electrolyte solution at 0.1M, and oxidation and reduction potentials were determined by CV measurement, and compared with ferrocene compounds as a reference.

When used for determining S ₁ And T ₁ In the case of fluorescence measurement of (2), the compound to be measured is 10 ^-5 M concentration was dissolved in toluene, and S was determined as the peak maximum by fluorescence measurement at room temperature ₁ In an extremely low temperature state, T was confirmed from the peak maximum value by phosphorescence measurement ₁ . When fluorescence measurement is performed at normal temperature and low temperature, excitation is performed by a 300nm light source to measure the fluorescence.

TABLE 2

It can be seen that ΔE of Compounds 1 to 9 used in the examples of the present application _st Are all less than 0.2eV, and are suitable as delayed fluorescence compounds. However, ΔE of T1 and T2 _st When the value is 0.2eV or more, the delayed fluorescence characteristic is not exhibited, and the efficiency is low.

ΔE of T3, T4 and 4CzIPN _st While less than 0.2eV corresponds to a delayed fluorescence compound, it is clear from table 1 that compounds 1 to 9 have good voltage and efficiency characteristics compared to T3, T4 and 4 CzIPN.

While the preferred examples of the present invention have been described above, the present invention is not limited to these examples, and may be modified and practiced in various forms within the scope of the invention as claimed and the detailed description of the invention, and the present invention is also within the scope of the invention.

Claims

1. A compound represented by the following chemical formula 1:

chemical formula 1

In the above-mentioned chemical formula 1,

ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms, a dibenzofuranyl group, a dibenzothienyl group, or an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 30 carbon atoms,

r1 to R4 are identical to or different from each other and are each independently hydrogen or deuterium,

r1 is an integer of 1 to 6,

r2 and r3 are each an integer of 1 to 7,

r4 is an integer of 1 to 5,

when r1 to r4 are 2 or more, respectively, structures in parentheses of 2 or more are the same or different from each other.

2. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1-1:

chemical formula 1-1

In the chemical formula 1-1 described above,

the definitions of X1, ar1 and Ar2 are the same as those in the chemical formula 1.

3. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1-2 or 1-3:

chemical formula 1-2

Chemical formulas 1-3

In the chemical formulas 1-2 and 1-3,

4. The compound of claim 1, wherein Ar1 and Ar2 are the same or different from each other, each independently being an aryl group having 6 to 30 carbon atoms.

5. The compound of claim 1, wherein the chemical formula 1 is selected from the following compounds:

/>

/>

/>

/>

6. the compound according to claim 1, wherein Δe of the compound represented by chemical formula 1 _st Less than 0.2eV.

7. The compound according to claim 1, wherein the compound represented by chemical formula 1 is a delayed fluorescence compound.

8. An organic light emitting device, comprising: a first electrode, a second electrode provided opposite to the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contains the compound according to any one of claims 1 to 7.

9. The organic light-emitting device of claim 8, wherein the organic layer comprises a light-emitting layer comprising the compound.

10. The organic light-emitting device of claim 8, wherein the organic layer comprises a light-emitting layer comprising the compound as a dopant for the light-emitting layer.

11. The organic light-emitting device according to claim 8, wherein the organic layer comprises a light-emitting layer comprising any one or more selected from an aromatic condensed ring derivative and a heterocyclic compound as a host of the light-emitting layer.

12. The organic light-emitting device of claim 11, wherein the host comprises any one or more of the following compounds:

/>

/>

/>

13. the organic light-emitting device according to claim 8, wherein the organic layer comprises a light-emitting layer containing the compound as a dopant of the light-emitting layer, and containing any one or more selected from an aromatic condensed ring derivative and a heterocyclic compound as a host of the light-emitting layer.

14. An organic light-emitting device according to claim 13 wherein the light-emitting layer comprises the dopant and the host in a weight ratio of 1:99 to 50:50.

15. The organic light-emitting device of claim 8, wherein the organic layer comprises a light-emitting layer further comprising a fluorescent emitter.