KR20220065950A - Compound and organic light emitting device comprising same - Google Patents

Abstract

The present specification provides a compound represented by chemical formula 1, and an organic light emitting device including 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 exemplary embodiment can improve efficiency, lower driving voltage, and/or improve lifetime characteristics of the organic light emitting device.

Description

Compound and organic light emitting device comprising the same

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

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up.

The development of new materials for the organic light emitting device as described above is continuously required.

KR 10-2010-0002153 A KR 10-1538534 B1 US 9373792 B2

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

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

[Formula 1]

In Formula 1,

X1 and X2 are the same as or different from each other, and each independently O; or S;

L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

one of R1 to R8 is bonded to L1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R9 is hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

Ar is represented by the following formula (A),

[Formula A]

In the formula A,

X3 is O; S; or CR101R102;

R101 and R102 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or an adjacent group bonded to each other to form a ring,

one of R11 to R14, Ra and Rb is bonded to L2, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group,

ra is an integer from 0 to 2, rb is an integer from 0 to 4,

When ra is 2, two Ra are the same as or different from each other, when rb is 2 or more, two or more Rb are the same as or different from each other,

n is an integer from 0 to 8,

When n is 2 or more, two or more R9 are the same as or different from each other.

In addition, one embodiment of the present specification is an anode; cathode; and at least one organic material layer provided between the anode and the cathode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above.

The compound described herein may be used as a material for an organic layer of an 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. In particular, the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection material. In addition, compared to the conventional organic light emitting device, there is an effect of a low driving voltage, high efficiency, and/or a long lifespan.

1 illustrates an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 6, and a cathode 10 are sequentially stacked.
2 is a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), hole blocking layer (7), electron transport layer (8) , an electron injection layer 9, a cathode 10, and a capping layer 11 are shown as an example of an organic light emitting device sequentially stacked.

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

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

In this specification, when a member is said to be located "on" another member, this includes not only a case in which a member is in contact with another member but also a case in which another member exists between the two members.

" 또는 점선은 화학식 또는 화합물에 결합되는 위치를 의미한다.In this specification, "

" or the dotted line means the position where it is bonded to the formula or compound.

In the present specification, the deuterium substitution rate of the compound is determined by using TLC-MS (Thin-Layer Chromatography/Mass Spectrometry), max. It is a method of calculating the substitution rate based on the value or a quantitative analysis method using NMR, adding DMF as an internal standard and calculating the D-substitution rate from the integral of the total peak using the integration ratio on 1H NMR. can

As used herein, "energy level" means an energy level. Therefore, the energy level is interpreted to mean the absolute value of the corresponding energy value. For example, when the energy level is low or deep, the absolute value increases in the negative direction from the vacuum level.

In the present specification, the highest occupied molecular orbital (HOMO) refers to a molecular orbital (highest occupied molecular orbital) in a region with the highest energy in a region where electrons can participate in bonding, and the lowest unoccupied molecular orbital (LUMO). is the molecular orbital function (lowest unoccupied molecular orbital) in which electrons are in the lowest energy region among the anti-bonding regions, and the HOMO energy level means the distance from the vacuum level to the HOMO. In addition, the LUMO energy level means the distance from the vacuum level to the LUMO.

In the present specification, the 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 can be measured using an atmospheric photoelectron spectrometer (RIKEN KEIKI Co., Ltd.: AC3), and the LUMO energy level can be calculated as a wavelength value measured through photoluminescence (PL). can

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

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

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group (-CN); nitro group; hydroxyl group; an alkyl group; cycloalkyl group; alkoxy group; a phosphine oxide group; aryloxy group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; alkenyl group; silyl group; boron group; amine group; aryl group; Or it means that it is substituted with one or more substituents selected from the group consisting of a heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; nitro group; hydroxyl group; amino group; silyl group; boron group; alkoxy group; aryloxy group; an alkyl group; cycloalkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; an alkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents.

In the present specification, N% substitution with deuterium means that N% of hydrogen available in the structure is substituted with deuterium. For example, if 25% of dibenzofuran is substituted with deuterium, it means that 2 out of 8 hydrogens of dibenzofuran are substituted with deuterium.

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

In the present specification, examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

In the present specification, the silyl group may be represented by the formula of -SiY _a Y _b Y _c , wherein Y _a , Y _b and Y _c 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, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. does not

In the present specification, the boron group may be represented by the formula of -BY _d Y _e , wherein Y _d and Y _e are each hydrogen; a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. Specifically, the boron group includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 30. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 10. Specific examples of the alkyl group include a methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, etc., but are not limited thereto.

In the present specification, the description of the above-described alkyl group may be applied, except that the arylalkyl group is substituted with an aryl group.

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, and the like, but is not limited thereto. .

The substituents containing an alkyl group, an alkoxy group, and other alkyl group moieties described herein include both straight-chain or pulverized forms.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10. 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, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the alkynyl group is a substituent including a triple bond between a carbon atom and a carbon atom, and may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the carbon number of the alkynyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkynyl group is 2 to 10.

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 carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like, but is not limited thereto.

In the present specification, the amine group is -NH ₂ , and the amine group may be substituted with the above-described alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to an exemplary embodiment, the carbon number of the amine group is 1 to 20. According to an exemplary embodiment, the carbon number of the amine group is 1 to 10. Specific examples of the substituted amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a 9,9-dimethylfluorenylphenylamine group, a pyridylphenylamine group, and a diphenylamine group. group, phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, dibenzofuranylphenylamine group, 9-methylanthracenylamine group, diphenylamine group, phenylnaphthylamine group, There is a ditolylamine group, a phenyltolylamine group, a diphenylamine group, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, a terphenyl group, or a quaterphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto not.

(1,1,4,4-테트라메틸-1,2,3,4-테트라하이드로나프탈렌기)를 포함할 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the substituted aryl group may include a structure in which an aliphatic hydrocarbon ring is condensed to an aryl group. According to an exemplary embodiment, the substituted aryl group may include a tetrahydronaphthalene group, and more specifically,

(1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene group), but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. In this case, the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.

,

,

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,

,

,

spirofluorenyl groups such as

(9,9-dimethyl fluorenyl group), and

a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, the present invention is not limited thereto.

In the present specification, the description of the above-described aryl group may be applied to the aryl group in the aryloxy group.

In the present specification, the description of the above-described alkyl group may be applied to the alkyl group in the alkylthiooxy group and the alkylsulfoxy group.

In the present specification, the description of the above-described aryl group may be applied to the aryl group in the arylthioxy group and the arylsulfoxy group.

In the present specification, the heterocyclic group is a cyclic group including at least one of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of the heterocyclic group include a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group , a carbazole group, a benzocarbazole group, a naphthobenzofuran group, a benzonaphthothiophene group, an indenocarbazole group, a triazinyl group, and the like, but are not limited thereto.

In the present specification, the description of the above-described heterocyclic group may be applied, except that the heteroaryl group is aromatic.

In the present specification, the description of the alkyl group may be applied except that the alkylene group is divalent.

In the present specification, the description of the aryl group may be applied except that the arylene group is divalent.

In the present specification, the description of the heterocyclic group may be applied, except that the divalent heterocycle is divalent.

In the present specification, in a substituted or unsubstituted ring formed by bonding with an adjacent group, "ring" is a hydrocarbon ring; or a heterocyclic ring.

The hydrocarbon ring may be an aromatic, aliphatic, or a condensed ring of an aromatic and an aliphatic group, and may be selected from examples of the cycloalkyl group or the aryl group.

In the present specification, the meaning of forming a ring by bonding with adjacent groups means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; a substituted or unsubstituted aromatic hydrocarbon ring; substituted or unsubstituted aliphatic heterocycle; substituted or unsubstituted aromatic heterocycle; Or it means to form a condensed ring thereof. The hydrocarbon ring means a ring consisting of only carbon and hydrogen atoms. The heterocycle means a ring including at least one selected from elements such as N, O, P, S, Si and Se. In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocycle and the aromatic heterocycle may be monocyclic or polycyclic.

In the present specification, the aliphatic hydrocarbon ring is a non-aromatic ring and refers to a ring consisting only of carbon and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, etc. However, the present invention is not limited thereto.

In the present specification, the aromatic hydrocarbon ring means an aromatic ring consisting only of carbon and hydrogen atoms. Examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, benzofluorene, spirofluorene, and the like, but is not limited thereto. In the present specification, the aromatic hydrocarbon ring may be interpreted as having the same meaning as the aryl group.

In the present specification, the aliphatic heterocycle refers to an aliphatic ring including one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine , thiocaine, and the like, but are not limited thereto.

In the present specification, the aromatic heterocycle refers to an aromatic ring including one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, paraazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thiazole. Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine , phenanthridine, diazanaphthalene, driazaindene, indole, indolizine, benzothiazole, benzoxazole, benzoimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzo carbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, indolocarbazole, indenocarbazole, and the like, but is not limited thereto.

Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiment of the present invention may be modified in various forms, and the scope of the present invention is not limited to the embodiments described below.

The compound represented by Formula 1 according to the present invention contains dibenzodioxin, phenothiazine or thianthrene in the anthracene structure, thereby changing the molecular orbital through a hetero atom in the electron transport region or hole transport region Since the characteristics of the transferred carriers are changed, there is an effect of improving the voltage, efficiency, and/or lifespan characteristics of the organic light emitting diode.

Additionally, when the compound represented by Formula 1 of the present invention includes deuterium, the efficiency and lifespan of the device are improved. Specifically, when hydrogen is replaced with deuterium, the chemical properties of the compound hardly change, but the physical properties of the deuterated compound change and the vibrational energy level is lowered. The compound substituted with deuterium can prevent reduction in intermolecular van der Waals force or decrease in quantum efficiency due to collisions due to intermolecular vibration. C-D bonds may also improve the stability of the compound.

Accordingly, when the compound represented by Chemical Formula 1 is applied to an organic light emitting device, an organic light emitting device having high efficiency, low voltage and/or long lifespan can be obtained.

Hereinafter, Chemical Formula 1 will be described in detail.

[Formula 1]

In Formula 1,

X1 and X2 are the same as or different from each other, and each independently O; or S;

L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

one of R1 to R8 is bonded to L1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R9 is hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

Ar is represented by the following formula (A),

[Formula A]

In the formula A,

X3 is O; S; or CR101R102;

R101 and R102 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or an adjacent group bonded to each other to form a ring,

one of R11 to R14, Ra and Rb is bonded to L2, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group,

ra is an integer from 0 to 2, rb is an integer from 0 to 4,

When ra is 2, two Ra are the same as or different from each other, when rb is 2 or more, two or more Rb are the same as or different from each other,

n is an integer from 0 to 8,

When n is 2 or more, two or more R9 are the same as or different from each other.

In an exemplary embodiment of the present specification, X1 and X2 are O.

In one embodiment of the present specification, X1 and X2 are S.

In an exemplary embodiment of the present specification, X1 is O, and X2 is S.

In an exemplary embodiment of the present specification, X1 is S, and X2 is O.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted monocyclic to 4-ring arylene group.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted monocyclic to tricyclic arylene group.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted monocyclic or bicyclic arylene group.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted C6-C20 arylene group.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; or an arylene group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; or an arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; a biphenylene group unsubstituted or substituted with deuterium; Or a naphthylene group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; phenylene group; biphenylene group; or a naphthylene group.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond, or represented by any one of the following structural formulas.

In the structural formula, the dotted line means a bonding position.

In one embodiment of the present specification, L1 is a direct bond; phenylene group; biphenylene group; or a naphthylene group.

In one embodiment of the present specification, L2 is a direct bond; phenylene group; biphenylene group; or a naphthylene group.

In one embodiment of the present specification, L2 is a direct bond; phenylene group; or a naphthylene group.

In an exemplary embodiment of the present specification, L1 and L2 are each unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, one of R1 to R8 is bonded to L1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, one of R1 to R8 is bonded to L1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted monocyclic or bicyclic aryl group; or a substituted or unsubstituted monocyclic to tricyclic heterocyclic group.

In an exemplary embodiment of the present specification, one of R1 to R8 is bonded to L1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted C 3 to C 60 cycloalkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, one of R1 to R8 is bonded to L1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 30 alkyl group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, one of R1 to R8 is bonded to L1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted C 3 to C 20 cycloalkyl group; a substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, one of R1 to R8 is bonded to L1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 30 alkyl group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C 2 to C 30 N, O or S-containing heterocyclic group.

In an exemplary embodiment of the present specification, one of R1 to R8 is bonded to L1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; an alkyl group having 1 to 30 carbon atoms that is unsubstituted or substituted with deuterium; a cycloalkyl group having 3 to 30 carbon atoms that is unsubstituted or substituted with deuterium; an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium; Or a C 2 to C 30 N, O or S-containing heterocyclic group unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, one of R1 to R8 is bonded to L1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted cyclopentyl group; a substituted or unsubstituted cyclohexyl group; a substituted or unsubstituted adamantyl group; a substituted or unsubstituted furan group; a substituted or unsubstituted thiophene group; a substituted or unsubstituted benzofuran group; a substituted or unsubstituted benzothiophene group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

In an exemplary embodiment of the present specification, one of R1 to R8 is bonded to L1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a propyl group unsubstituted or substituted with deuterium; a butyl group unsubstituted or substituted with deuterium; a phenyl group unsubstituted or substituted with deuterium; a biphenyl group unsubstituted or substituted with deuterium; a terphenyl group unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium; a cyclopentyl group unsubstituted or substituted with deuterium; a cyclohexyl group unsubstituted or substituted with deuterium; adamantyl group unsubstituted or substituted with deuterium; a furan group unsubstituted or substituted with deuterium; a thiophene group unsubstituted or substituted with deuterium; a benzofuran group unsubstituted or substituted with deuterium; a benzothiophene group unsubstituted or substituted with deuterium; a dibenzofuran group unsubstituted or substituted with deuterium; Or a dibenzothiophene group unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, one of R1 to R8 is bonded to L1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted cyclopentyl group; a substituted or unsubstituted cyclohexyl group; a substituted or unsubstituted furan group; a substituted or unsubstituted thiophene group; a substituted or unsubstituted benzofuran group; Or a substituted or unsubstituted benzothiophene group.

In an exemplary embodiment of the present specification, one of R1 to R8 is bonded to L1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; i-propyl group; t-butyl group; a phenyl group unsubstituted or substituted with deuterium; biphenyl group; naphthyl group; cyclopentyl group; cyclohexyl group; furan group; thiophene group; benzofuran group; or a benzothiophene group.

In an exemplary embodiment of the present specification, one of R1 to R8 is bonded to L1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; i-propyl group; t-butyl group; a phenyl group unsubstituted or substituted with deuterium; naphthyl group; cyclopentyl group; cyclohexyl group; furan group; thiophene group; benzofuran group; or a benzothiophene group.

In an exemplary embodiment of the present specification, one of R1 to R8 is bonded to L1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; i-propyl group; t-butyl group; a phenyl group unsubstituted or substituted with deuterium; cyclohexyl group; or a thiophene group.

In one embodiment of the present specification, R1 is combined with L1.

In one embodiment of the present specification, R2 is combined with L1.

In one embodiment of the present specification, R3 is combined with L1.

In one embodiment of the present specification, R4 is combined with L1.

In one embodiment of the present specification, R5 is combined with L1.

In one embodiment of the present specification, R6 is combined with L1.

In one embodiment of the present specification, R7 is combined with L1.

In one embodiment of the present specification, R8 is combined with L1.

In an exemplary embodiment of the present specification, the remainder not bonded to L1 among R1 to R8 is hydrogen; or deuterium.

In the exemplary embodiment of the present specification, the remainder not bonded to L1 among R1 to R8 is hydrogen.

In an exemplary embodiment of the present specification, R1 to R8 are each unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, R9 is hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, R9 is hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted C 3 to C 60 cycloalkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, R9 is hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C 1 to C 30 alkyl group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R9 is hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted C 3 to C 20 cycloalkyl group; a substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R9 is hydrogen; or deuterium.

In an exemplary embodiment of the present specification, R9 is hydrogen.

In an exemplary embodiment of the present specification, R9 is unsubstituted or substituted with deuterium.

In one embodiment of the present specification, X3 is O; S; or CR101R102.

In one embodiment of the present specification, X3 is O; or S.

In one embodiment of the present specification, X3 is CR101R102.

In an exemplary embodiment of the present specification, X3 is O.

In one embodiment of the present specification, X3 is S.

In an exemplary embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or an adjacent group bonded to each other to form a ring.

In an exemplary embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently a substituted or unsubstituted C 1 to C 60 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or bonding with an adjacent group to form an aromatic hydrocarbon ring having 6 to 60 carbon atoms.

In an exemplary embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently a substituted or unsubstituted C 1 to C 30 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or bonding with an adjacent group to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently a substituted or unsubstituted C 1 to C 20 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or bonding with an adjacent group to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently a substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group, or a substituted or unsubstituted fluorene ring by combining with an adjacent group.

In an exemplary embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently a methyl group; or a phenyl group, or a fluorene ring by bonding with adjacent groups.

In an exemplary embodiment of the present specification, R101 and R102 are each unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, one of R11 to R14, Ra and Rb binds to L2.

In an exemplary embodiment of the present specification, one of R11 to R14 and Ra binds to L2.

In one embodiment of the present specification, R11 is combined with L2.

In one embodiment of the present specification, R12 is combined with L2.

In one embodiment of the present specification, R13 is combined with L2.

In one embodiment of the present specification, R14 is combined with L2.

In one embodiment of the present specification, Ra binds to L2.

In one embodiment of the present specification, Rb is combined with L2.

In an exemplary embodiment of the present specification, the rest of R11 to R14, Ra and Rb that are not bound to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group.

In an exemplary embodiment of the present specification, the rest of R11 to R14, Ra and Rb that are not bound to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, the rest of R11 to R14, Ra and Rb that are not bound to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted C 3 to C 60 cycloalkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, the rest of R11 to R14, Ra and Rb that are not bound to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C 1 to C 30 alkyl group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, the rest of R11 to R14, Ra and Rb that are not bound to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted C 3 to C 20 cycloalkyl group; a substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, the rest of R11 to R14, Ra and Rb that are not bound to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, the rest of R11 to R14, Ra and Rb that are not bound to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; an alkyl group unsubstituted or substituted with deuterium or an alkyl group; or an aryl group unsubstituted or substituted with deuterium or an alkyl group.

In an exemplary embodiment of the present specification, the rest of R11 to R14, Ra and Rb that are not bound to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; an alkyl group; or an aryl group unsubstituted or substituted with deuterium or an alkyl group.

In an exemplary embodiment of the present specification, the rest of R11 to R14, Ra and Rb that are not bound to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

In an exemplary embodiment of the present specification, the rest of R11 to R14, Ra and Rb that are not bound to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a butyl group unsubstituted or substituted with deuterium or an alkyl group; a phenyl group unsubstituted or substituted with deuterium or an alkyl group; a biphenyl group unsubstituted or substituted with deuterium or an alkyl group; or a naphthyl group unsubstituted or substituted with deuterium or an alkyl group.

In an exemplary embodiment of the present specification, the rest of R11 to R14, Ra and Rb that are not bound to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; butyl group; a phenyl group unsubstituted or substituted with deuterium or an alkyl group having 1 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with deuterium or an alkyl group having 1 to 20 carbon atoms; or a naphthyl group unsubstituted or substituted with deuterium or an alkyl group having 1 to 20 carbon atoms.

In an exemplary embodiment of the present specification, the rest of R11 to R14, Ra and Rb that are not bound to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; butyl group; a phenyl group unsubstituted or substituted with deuterium or an alkyl group having 1 to 10 carbon atoms; a biphenyl group unsubstituted or substituted with deuterium or an alkyl group having 1 to 10 carbon atoms; or a naphthyl group unsubstituted or substituted with deuterium or an alkyl group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present specification, the rest of R11 to R14, Ra and Rb that are not bound to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; butyl group; a phenyl group unsubstituted or substituted with deuterium or an alkyl group having 1 to 10 carbon atoms; biphenyl group; or a naphthyl group.

In an exemplary embodiment of the present specification, the rest of R11 to R14, Ra and Rb that are not bound to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; butyl group; a phenyl group unsubstituted or substituted with deuterium, a methyl group, a propyl group, or a butyl group; biphenyl group; or a naphthyl group.

In an exemplary embodiment of the present specification, the rest of R11 to R14, Ra and Rb that are not bound to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; t-butyl group; a phenyl group unsubstituted or substituted with deuterium, a methyl group, an i-propyl group, or a t-butyl group; biphenyl group; or a naphthyl group.

In an exemplary embodiment of the present specification, the rest of R11 to R14, Ra and Rb that are not bound to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; t-butyl group; a phenyl group unsubstituted or substituted with deuterium or a t-butyl group; or a naphthyl group.

In an exemplary embodiment of the present specification, the rest of R11 to R14, Ra and Rb that are not bound to L2 are the same as or different from each other, and each independently hydrogen; or deuterium.

In an exemplary embodiment of the present specification, the remainder not bonded to L2 among R11 to R14, Ra and Rb is hydrogen.

In an exemplary embodiment of the present specification, R11 to R14, Ra and Rb are each unsubstituted or substituted with deuterium.

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

In one embodiment of the present specification, ra is 1 or 2.

In one embodiment of the present specification, ra is 2.

In one embodiment of the present specification, rb is 0.

In one embodiment of the present specification, rb is 1.

In one embodiment of the present specification, rb is 2.

In one embodiment of the present specification, rb is 4.

In one embodiment of the present specification, n is 0.

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

In one embodiment of the present specification, n is 8.

In an exemplary embodiment of the present specification, Formula A is represented by any one of Formulas A1 to A6 below.

[Formula A1] [Formula A2] [Formula A3]

[Formula A4] [Formula A5] [Formula A6]

In Formulas A1 to A6, the definition of X3 is the same as the definition in Formula A,

one of R11 to R14, Ra1, Ra2, and Rb1 to Rb4 is bonded to L2, the others are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group.

In the exemplary embodiment of the present specification, the above definitions of Ra and Rb may be applied to Ra1, Ra2, and Rb1 to Rb4.

In one embodiment of the present specification, Ra1 binds to L2.

In one embodiment of the present specification, Ra2 binds to L2.

In one embodiment of the present specification, Rb1 is combined with L2.

In one embodiment of the present specification, Rb2 is combined with L2.

In one embodiment of the present specification, Rb3 is combined with L2.

In one embodiment of the present specification, Rb4 is combined with L2.

In an exemplary embodiment of the present specification, Formula A is represented by any one of Formulas B1 to B5 below.

[Formula B1] [Formula B2]

[Formula B3] [Formula B4] [Formula B5]

In Formulas B1 to B5, definitions of R11 to R14, Ra, Rb, ra and rb are the same as those in Formula 1 above.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 1-1 or 1-2.

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2, the definitions of X1 to X3, L1, L2, R1 to R9, Ra, Rb, n, ra and rb are the same as the definitions in Formula 1 above,

R101 is hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group,

r101 is an integer from 0 to 4, r101' is an integer from 0 to 3, and when r101 and r101' are each 2 or more, two or more R101 are the same as or different from each other,

ra' is 0 or 1.

In the exemplary embodiment of the present specification, the above-described definitions of R11 to R14 may be applied to R101.

In an exemplary embodiment of the present specification, R101, Ra and Rb are the same as or different from each other, and each independently hydrogen; or deuterium.

In an exemplary embodiment of the present specification, R101, Ra, and Rb are the same as or different from each other, and are each independently hydrogen.

In an exemplary embodiment of the present specification, Rb is a cyano group; an alkyl group; or an aryl group unsubstituted or substituted with deuterium or an alkyl group, and rb is 1 or more.

In an exemplary embodiment of the present specification, r101 is 1 or 2.

In an exemplary embodiment of the present specification, r101' is 1 or 2.

In the exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 2-1 or 2-2.

[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2, definitions of X1, X2, L1, L2, R1 to R9, Ar, and n are the same as in Formula 1 above.

In an exemplary embodiment of the present specification, at least one of the groups not bonded to L2 among R11 to R14, Ra and Rb is a cyano group; a substituted or unsubstituted C 1 to C 30 alkyl group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C 2 to C 30 N, O or S-containing heterocyclic group.

In an exemplary embodiment of the present specification, at least one of the groups not bonded to L2 among R11 to R14, Ra and Rb is a cyano group; a substituted or unsubstituted C 1 to C 30 alkyl group; or a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, at least one of the groups not bonded to L2 among R11 to R14, Ra and Rb is a cyano group; an alkyl group having 1 to 20 carbon atoms; or an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with deuterium or an alkyl group having 1 to 20 carbon atoms.

In an exemplary embodiment of the present specification, at least one of the groups not bonded to L2 among R11 to R14, Ra and Rb is a cyano group; a substituted or unsubstituted butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

In an exemplary embodiment of the present specification, at least one of the groups not bonded to L2 among R11 to R14, Ra and Rb is not hydrogen.

In an exemplary embodiment of the present specification, one of R1 to R8 is bonded to L1, and at least one of the groups not bonded to L1 is a substituted or unsubstituted C1-C30 alkyl group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C 2 to C 30 N, O or S-containing heterocyclic group.

In an exemplary embodiment of the present specification, one of R1 to R8 is bonded to L1, and at least one of the groups not bonded to L1 is an alkyl group having 1 to 30 carbon atoms; a cycloalkyl group having 3 to 30 carbon atoms; an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium; or a heterocyclic group containing N, O or S having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, one of R1 to R8 is bonded to L1, and at least one of the groups not bonded to L1 is a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted cyclopentyl group; a substituted or unsubstituted cyclohexyl group; a substituted or unsubstituted furan group; a substituted or unsubstituted thiophene group; a substituted or unsubstituted benzofuran group; Or a substituted or unsubstituted benzothiophene group.

In the exemplary embodiment of the present specification, when R1 is combined with L1, at least one of R2 to R8 is not hydrogen.

In the exemplary embodiment of the present specification, when R2 is combined with L1, at least one of R1 and R3 to R8 is not hydrogen

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of Chemical Formulas 3-1 to 3-7 and Chemical Formulas 4-1 to 4-7.

In Formulas 3-1 to 3-7 and Formulas 4-1 to 4-7, the definitions of X1, X2, L1, L2 and Ar are the same as those in Formula 1,

G1 to G8 are the same as or different from each other, and each independently deuterium; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In the exemplary embodiment of the present specification, the above-described definitions of R1 to R8 may be applied to G1 to G8, except that hydrogen is excluded.

In an exemplary embodiment of the present specification, the compound represented by Formula 1 is substituted at least 40% with deuterium. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 50% or more. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 60% or more. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 70% or more. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 80% or more. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 90% or more. In another exemplary embodiment, the compound represented by Formula 1 is 100% substituted with deuterium.

In an exemplary embodiment of the present specification, the compound represented by Formula 1 contains 40% to 60% of deuterium. In another exemplary embodiment, the compound represented by Formula 1 contains 40% to 80% of deuterium. In another exemplary embodiment, the compound represented by Formula 1 contains 60% to 80% of deuterium. In another exemplary embodiment, the compound represented by Formula 1 contains 80% to 100% of deuterium.

In the exemplary embodiment of the present specification, L1 and L2 may be the same as or different from each other, and may each independently be substituted with deuterium.

In the exemplary embodiment of the present specification, R1 and R9 may be the same as or different from each other, and may each independently be substituted with deuterium.

In the exemplary embodiment of the present specification, Ar may be substituted with deuterium.

In an exemplary embodiment of the present specification, R101 and R102 may be the same as or different from each other, and each independently may be substituted with deuterium.

In the exemplary embodiment of the present specification, R11 to R14, Ra and Rb may be the same as or different from each other, and each independently may be substituted with deuterium.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following compounds.

For the compound represented by Formula 1 according to an exemplary embodiment of the present specification, a core structure may be prepared as in Preparation Examples 1 to 7 to be described later. Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.

In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by Formula 1 above. In addition, in the present specification, the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents into the core structure of the structure as described above.

In addition, the present specification provides an organic light emitting device including the above-described compound.

The organic light emitting device according to the present specification includes an anode; cathode; and at least one organic material layer provided between the anode and the cathode, wherein at least one of the organic material layers comprises a compound represented by Formula 1 above.

The organic light emitting device of the present specification may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming an organic material layer using the compound of Formula 1 above.

The compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

The organic material layer of the organic light emitting device of the present specification 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, the organic light emitting device of the present invention comprises at least one of a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer as an organic material layer. It may have a structure containing However, the structure of the organic light emitting device of the present specification is not limited thereto and may include a smaller number or a larger number of organic material layers.

In the organic light emitting device of the present specification, 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, the hole transport layer, or the hole injection and transport layer is a compound represented by the above-mentioned Formula 1 may include

In the organic light emitting device of the present specification, the organic material layer may include a hole transport layer or a hole injection layer, and the hole transport layer or the hole injection layer may include the compound represented by Chemical Formula 1 described above.

In an exemplary embodiment of the present specification, the organic material layer includes an electron injection layer, an electron transport layer, an electron injection and transport layer or a hole blocking layer, and the electron injection layer, the electron transport layer, the electron injection and transport layer or the hole blocking layer is the above-described The compound represented by Formula 1 may be included.

In the organic light emitting device of the present specification, the organic material layer includes an electron transport layer, an electron injection layer, or an electron transport and injection layer, and the electron transport layer, the electron injection layer, or the electron transport and injection layer is represented by the above formula (1) compounds may be included.

In an exemplary embodiment of the present specification, the organic material layer may include an electron control layer, and the electron control layer may include the compound represented by Formula 1 described above.

In an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 described above.

In an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 as a host.

In an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound represented by Formula 1 as a blue host.

In the exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound represented by Formula 1 as a dopant.

In the exemplary embodiment of the present specification, the organic light emitting device is a green organic light emitting device in which the light emitting layer includes the compound represented by Formula 1 as a host.

According to an exemplary embodiment of the present specification, the organic light emitting device is a red organic light emitting device in which the light emitting layer includes the compound represented by Formula 1 as a host.

In another exemplary embodiment, the organic light emitting device is a blue organic light emitting device in which the light emitting layer includes the compound represented by Formula 1 as a host.

In the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 as a host, and may further include a dopant. In this case, the content of the dopant may be included in an amount of 1 part by weight to 60 parts by weight, preferably 1 part by weight to 10 parts by weight, based on 100 parts by weight of the host.

At this time, as the dopant, a phosphorescent material such as (4,6-F2ppy) ₂ Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), PFO-based polymer, PPV-based polymer A fluorescent material such as a polymer, an anthracene-based compound, a pyrene-based compound, or a boron-based compound may be used, but is not limited thereto.

In another exemplary embodiment, the organic material layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Formula 1 above.

In the organic light emitting device according to the exemplary embodiment of the present specification, the light emitting layer further includes a fluorescent dopant or a phosphorescent dopant. In this case, the dopant in the emission layer is included in an amount of 1 to 50 parts by weight based on 100 parts by weight of the host.

In an exemplary embodiment of the present specification, the thickness of the organic material layer including the compound represented by Formula 1 is 10 Å to 500 Å, in one example 50 Å to 400 Å, and according to another embodiment 100 Å to 400 Å. is Å.

In the organic light emitting diode according to the exemplary embodiment of the present specification, the maximum emission peak of the organic material layer is 400 nm to 500 nm. In another exemplary embodiment, the maximum emission peak of the organic material layer is 400 nm to 470 nm.

As another example, the organic material layer may include an emission layer, the emission layer may include the compound represented by Formula 1 as a host, and may further include an additional host.

In an exemplary embodiment of the present specification, the dopant includes an arylamine-based compound, a heterocyclic compound including boron and nitrogen, or an Ir complex.

In the exemplary embodiment of the present specification, the fluorescent dopant may be selected from the following structures, but is not limited thereto.

In an exemplary embodiment of the present specification, an Ir complex may be used as the phosphorescent dopant, and for example, any one of the following structures may be used, but is not limited thereto.

In an exemplary embodiment of the present specification, the light emitting layer including the compound represented by Formula 1 has a blue color.

According to an example, the content of the compound represented by Formula 1 is 70 parts by weight to 99.99 parts by weight based on 100 parts by weight of the total of the host and dopant of the emission layer; Preferably, 80 parts by weight to 99.9 parts by weight; More preferably, it is 90 parts by weight to 99.5 parts by weight.

In an exemplary embodiment of the present specification, the organic material layer includes the compound, and the bandgap energy of the compound is 2.9 eV or more.

The organic light emitting device of the present specification may further include an organic material layer of at least one of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer. can

In an exemplary embodiment of the present specification, the organic light emitting device includes an anode; cathode; and two or more organic material layers provided between the anode and the cathode, wherein at least one of the two or more organic material layers includes the compound represented by Formula 1 above.

In an exemplary embodiment of the present specification, two or more organic material layers may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a hole transport and hole injection layer, and an electron blocking layer.

In one embodiment of the present specification, the two or more organic material layers may be selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, an electron control layer, and a hole blocking layer.

In the exemplary embodiment of the present specification, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound represented by Formula 1 above. Specifically, in an exemplary embodiment of the present specification, the compound represented by Formula 1 may be included in one of the two or more electron transport layers, or may be included in each of the two or more electron transport layers.

In addition, in the exemplary embodiment of the present specification, when the compound is included in each of the two or more electron transport layers, materials other than the compound represented by Formula 1 may be the same or different from each other.

When the organic material layer including the compound represented by Formula 1 is an electron transport layer, the electron transport layer may further include an n-type dopant. As the n-type dopant, those known in the art may be used, for example, a metal or a metal complex may be used. For example, the electron transport layer including the compound represented by Formula 1 may further include lithium quinolate (LiQ).

In an exemplary embodiment of the present specification, the organic material layer includes two or more hole transport layers, and at least one of the two or more hole transport layers includes the compound represented by Formula 1 above. Specifically, in an exemplary embodiment of the present specification, the compound represented by Formula 1 may be included in one of the two or more hole transport layers, and may be included in each of the two or more hole transport layers.

In addition, in one embodiment of the present specification, when the compound represented by Formula 1 is included in each of the two or more hole transport layers, materials other than the compound represented by Formula 1 may be the same or different from each other. there is.

In an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer containing a compound including an arylamine group, a carbazolyl group or a benzocarbazolyl group in addition to the organic material layer including the compound represented by Formula 1 may include

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

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

In the organic light emitting device of the present invention, the organic material layer may include an electron blocking layer, the electron blocking layer may be a material known in the art.

The organic light emitting device may have, for example, a stacked structure as follows, but is not limited thereto.

(1) anode/hole transport layer/light emitting layer/cathode

(2) anode / hole injection layer / hole transport layer / light emitting layer / cathode

(3) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / cathode

(4) anode / hole transport layer / light emitting layer / electron transport layer / cathode

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

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

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

(8) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode

(9) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

(10) anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

(11) anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

(12) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

(13) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

(14) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

(15) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

(16) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

(17) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

The structure of the organic light emitting diode of the present specification may have a structure as shown in FIGS. 1 and 2 , but is not limited thereto.

1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 6, and a cathode 10 are sequentially stacked. In such a structure, the compound may be included in the light emitting layer 6 .

2 is a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), hole blocking layer (7), electron transport layer (8) , the electron injection layer 9 , the cathode 10 and the capping layer 11 are sequentially stacked, the structure of the organic light emitting device is exemplified. In this structure, the compound is the hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), hole blocking layer (7), electron transport layer (8) or electron injection may be included in layer 9 .

For example, the organic light emitting device according to the present specification uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal or a conductive metal oxide or an alloy thereof on a substrate. is deposited to form an anode, and an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer and an electron injection layer is formed thereon, and then a material that can be used as a cathode is deposited thereon. can be In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The organic material layer may further include at least one of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.

The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, an electron injection and transport layer, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron transport and injection layer, etc., but is not limited thereto, and may have a single layer structure can In addition, the organic layer is formed using a variety of polymer materials in a smaller number by a solvent process rather than a vapor deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.

The anode is an electrode for injecting holes, and as the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO, Indium Tin Oxide), and indium zinc oxide (IZO, Indium Zinc Oxide); ZnO: Al or SnO ₂ : Combination of metals and oxides such as Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode is an electrode for injecting electrons, and 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 cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer that smoothly injects holes from the anode into the light emitting layer. As the hole injection material, holes can be well injected from the anode at a low voltage, and the highest occupied (HOMO) of the hole injection material is The molecular orbital) is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto. The hole injection layer may have a thickness of 1 nm to 150 nm. When the thickness of the hole injection layer is 1 nm or more, there is an advantage in that the hole injection characteristics can be prevented from being deteriorated, and when it is 150 nm or less, the thickness of the hole injection layer is too thick, so that the driving voltage is increased to improve hole movement There are advantages to avoiding this.

The hole transport layer may serve to facilitate hole transport. As the hole transport material, a material capable of receiving holes from the anode or hole injection layer and transferring them to the light emitting layer is suitable, and a material having high hole mobility is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

An additional hole buffer layer may be provided between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the art.

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

The light emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include the aforementioned compound of Formula 1; 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

Examples of the host material for the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

When the emission layer emits red light, the emission dopant is PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium) ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq ₃ (tris(8-hydroxyquinolino)aluminum) may be used, but is not limited thereto. When the emission layer emits green light, a phosphor such as Ir(ppy) ₃ (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant. However, the present invention is not limited thereto. When the light-emitting layer emits blue light, the light-emitting dopant includes a phosphorescent material such as (4,6-F2ppy) ₂ Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), A fluorescent material such as a PFO-based polymer or a PPV-based polymer may be used, but is not limited thereto.

The hole blocking layer is a layer that blocks the inflow of holes from the light emitting layer to the cathode and controls the performance of the entire device by controlling electrons flowing into the light emitting layer. The hole blocking material is preferably a compound having the ability to prevent the inflow of holes from the light emitting layer to the cathode and to control electrons injected into the light emitting layer or the light emitting material. As the hole blocking material, an appropriate material may be used according to the composition of the organic material layer used in the device. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but is not limited thereto.

The electron transport layer may serve to facilitate the transport of electrons. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high electron mobility is suitable. Specific examples include the above-mentioned compound or Al complex of 8-hydroxyquinoline; complexes containing Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may have a thickness of 1 nm to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage that the electron transport properties can be prevented from being deteriorated, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from being raised to improve the movement of electrons. There are advantages that can be

The electron injection layer may serve to facilitate electron injection. The electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, prevents the movement of excitons generated in the light emitting layer to the hole injection layer, and , a compound having excellent thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

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

Hereinafter, examples will be given to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various other forms, and the scope of the present application is not to be construed as being limited to the embodiments described below. The embodiments of the present application are provided to more completely explain the present specification to those of ordinary skill in the art.

Preparation Example 1 (Synthesis of Compounds A1 to A6)

SM1 (leq), SM2 (leq) and potassium carbonate (3eq) were added to dimethylformamide (DMF) (300ml) and stirred under reflux. After completion of the reaction, cool to room temperature and filter. After extraction with water and chloroform at room temperature, the white solid was columned with ethyl acetate and hexane to prepare Compound A.

Specifically, compounds A1 to A5 were synthesized using the compounds shown in Table A below for SM1 and SM2, respectively.

[Table A]

Preparation Example 2 (Synthesis of Compounds B1 to B4 and C1 to C6)

After adding SM1 (1eq) and SM2 (1.05eq) to tetrahydrofuran (excess), 2M aqueous potassium carbonate solution (30 times volume ratio compared to THF) was added, and tetrakistriphenyl-phosphinopalladium (2 mol%) was added. Then, the mixture was heated and stirred for 10 hours. After the reaction was terminated by lowering the temperature to room temperature, the potassium carbonate aqueous solution was removed and the layers were separated. After confirming the completion of the reaction, the temperature was lowered to room temperature, the solvent was removed, and the compound B was purified by recrystallization using ethyl acetate and hexane.

Specifically, compounds B1 to B4 were synthesized using the compounds shown in Table B below for SM1 and SM2, respectively.

[Table B]

Compounds C1 to C6 of [Table C] were synthesized in the same manner except that SM1 and SM2 were changed as follows in the synthesis method of B1 to B7.

[Table C]

Preparation Example 3 (Synthesis of Compounds D1 to D11)

SM1 (1eq) and SM2 (1.3eq) were added to 1,4-dioxane (12 parts by weight based on 1 part by weight of SM1), potassium acetate (3eq) was added, and stirred and refluxed. Palladium acetate (0.02eq) and tricyclohexylphosphine (0.04eq) were stirred in 1,4-dioxane for 5 minutes, added, and 2 hours later, after confirming the completion of the reaction, cooled to room temperature. After adding ethanol and water, the mixture was filtered and purified by recrystallization with ethyl acetate and ethanol to prepare Compound D.

Specifically, compounds D1 to D11 were synthesized using the compounds shown in Table D below for SM1 and SM2, respectively.

[Table D]

Preparation Example 4 (Synthesis of Compounds E1 to E16)

After adding SM1 (1eq) and SM2 (1.05eq) to tetrahydrofuran (excess), 2M aqueous potassium carbonate solution (30 times by volume compared to THF) was added, and tetrakistriphenyl-phosphinopalladium (2 mol%) was added. Then, the mixture was heated and stirred for 10 hours. After the reaction was terminated by lowering the temperature to room temperature, the potassium carbonate aqueous solution was removed and the layers were separated. After confirming the completion of the reaction, the temperature was lowered to room temperature, the solvent was removed, and the compound E was purified by recrystallization using toluene.

Specifically, compounds E1 to E16 were synthesized using the compounds shown in Table E below for SM1 and SM2, respectively.

[Table E]

Preparation Example 5 (Synthesis of Compounds F1 to F16)

SM1 (leq) was dissolved in chloroform (excess) and the temperature was stabilized at 0 °C, then N-bromosuccinimide (leq) dissolved in dimethylformamide was added dropwise, and the temperature was raised to room temperature. After confirming the completion of the reaction, a saturated aqueous solution of Na ₂ S ₂ O ₃ was added dropwise as much as the amount of chloroform added, followed by extraction and purification by recrystallization using toluene to prepare Compound F.

Specifically, compounds F1 to F16 were synthesized using the compounds shown in [Table F] below in SM1.

[Table F]

Preparation Example 6 (Synthesis of Compounds 1 to 25)

After adding SM1 (1eq) and SM2 (1.05eq) to tetrahydrofuran (excess), 2M aqueous potassium carbonate solution (30 times volume ratio compared to THF) was added, and tetrakistriphenyl-phosphinopalladium (2 mol%) was added. Then, the mixture was heated and stirred for 10 hours. After the reaction was terminated by lowering the temperature to room temperature, the potassium carbonate aqueous solution was removed and the layers were separated. After confirming the completion of the reaction, the temperature was lowered to room temperature, the solvent was removed, and the following compounds 1 to 25 were prepared by recrystallization using toluene.

Specifically, compounds 1 to 25 were synthesized using the compounds shown in Table 1 below for SM1 and SM2, respectively.

[Table 1]

Among the above reactants, compounds corresponding to SM2 were synthesized with reference to US Patent Publication No. US 9373792.

Preparation 7 (Synthesis of Compounds 26 to 28)

The reactant (leq), trifluoromethanesulfonic acid (cat.) was added to C ₆ D ₆ (10-50 times the mass ratio of the reactant) and stirred at 70 ° C. for 10 to 100 minutes. After completion of the reaction, D ₂ O (excess) was added and stirred for 30 minutes, followed by dropwise addition of trimethylamine (excess). The reaction solution was transferred to a separatory funnel, and extracted with water and chloroform. The extract was dried over MgSO ₄ , and recrystallized by heating with toluene to obtain compounds 26 to 28 as shown in Table 2 below.

[Table 2]

For the substitution of deuterium for the above product, reference was made to the literature of Korean Patent Publication No. 10-1538534.

<Example 1> Preparation of OLED

As an anode, a substrate on which 70/1000/70 Å of ITO/Ag/ITO was deposited was cut into a size of 50 mm x 50 mm x 0.5 mm, put in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent used was a product of Fischer Co., and the distilled water was manufactured by Millipore Co. Secondary filtered distilled water was used as a filter of the product. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.

On the prepared anode, HI-1 was thermally vacuum deposited to a thickness of 50 Å to form a hole injection layer, and HT1, a material for transporting holes, was vacuum-deposited thereon to a thickness of 1150 Å to form a hole transport layer. Then, an electron blocking layer was formed using EB1 (150 Å), and then the host compound 1 synthesized according to Preparation Example 6 and the dopant BD1 (2 parts by weight based on 100 parts by weight of the host and dopant) were added to 360 Å. A light emitting layer was formed by vacuum deposition to a thickness.

Thereafter, ET1 was deposited by 50 Å to form a hole blocking layer, and the compound ET2 and Liq were mixed at a ratio of 7:3 to form an electron transport layer having a thickness of 250 Å. Magnesium and lithium fluoride (LiF) having a thickness of 50 Å were sequentially formed as an electron injection layer, and then 200 Å was formed as a cathode with magnesium and silver (weight ratio 1:4), and then CP1 was deposited to 600 Å to complete the device. In the above process, the deposition rate of the organic material was maintained at 1 Å/sec.

<Examples 2 to 34 and Comparative Examples 1 to 18>

Compounds 2 to 28 synthesized according to Preparation Examples 6 and 7 and the following Comparative Examples compounds BH1 to BH14 were used as a host material for the light emitting layer, and BD1 or BD2 was used as a dopant material for the light emitting layer to be organic in the same manner as in Example 1. A light emitting device was manufactured.

When a current of 20 mA/cm ² was applied to the organic light emitting devices prepared in Examples and Comparative Examples, voltage, efficiency, color coordinates and lifetime were measured, and the results are shown in Table 3 below. T95 denotes the time required for the luminance to decrease from the initial luminance to 95%.

Experimental example
20 mA/cm2 host dopant Voltage (V)
(@20mA/cm ² ) Efficiency (Cd/A)
(@20mA/cm ² ) color coordinates
(x,y) life span
(T95, h)
(@20mA/cm ² ) Example 1 compound 1 BD1 3.45 6.68 (0.135, 0.143) 50.1 Example 2 compound 2 BD1 3.44 6.66 (0.134, 0.142) 52.1 Example 3 compound 3 BD1 3.48 6.61 (0.135, 0.141) 53.8 Example 4 compound 4 BD1 3.38 6.58 (0.134, 0.149) 55.5 Example 5 compound 5 BD1 3.46 6.64 (0.134, 0.141) 53.1 Example 6 compound 6 BD1 3.25 6.60 (0.134, 0.142) 54.8 Example 7 compound 7 BD1 3.45 6.70 (0.134, 0.147) 53.1 Example 8 compound 8 BD1 3.40 6.65 (0.135, 0.143) 54.4 Example 9 compound 9 BD1 3.50 6.66 (0.134, 0.142) 55.0 Example 10 compound 10 BD1 3.48 6.70 (0.136, 0.142) 58.1 Example 11 compound 11 BD1 3.46 6.68 (0.136, 0.142) 50.7 Example 12 compound 12 BD1 3.44 6.55 (0.136, 0.142) 59.5 Example 13 compound 13 BD1 3.48 6.59 (0.136, 0.143) 54.9 Example 14 compound 14 BD1 3.42 6.60 (0.135, 0.141) 53.0 Example 15 compound 15 BD1 3.48 6.67 (0.136, 0.143) 53.3 Example 16 compound 16 BD1 3.28 6.59 (0.134, 0.140) 55.1 Example 17 compound 17 BD1 3.26 6.60 (0.136, 0.143) 56.7 Example 18 compound 18 BD1 3.48 6.64 (0.134, 0.147) 55.6 Example 19 compound 19 BD1 3.30 6.71 (0.136, 0.142) 56.5 Example 20 compound 20 BD1 3.22 6.61 (0.136, 0.143) 53.8 Example 21 compound 21 BD1 3.44 6.58 (0.134, 0.147) 52.1 Example 22 compound 22 BD1 3.46 6.63 (0.134, 0.146) 53.0 Example 23 compound 23 BD1 3.25 6.59 (0.135, 0.141) 52.8 Example 24 compound 24 BD1 3.28 6.61 (0.134, 0.149) 54.4 Example 25 compound 25 BD1 3.26 6.60 (0.135, 0.141) 50.9 Example 26 compound 26 BD1 3.44 6.65 (0.134, 0.142) 70.8 Example 27 compound 27 BD1 3.47 6.65 (0.134, 0.141) 71.4 Example 28 compound 28 BD1 3.51 6.65 (0.134, 0.142) 70.9 Example 29 compound 2 BD2 3.53 6.89 (0.134, 0.128) 49.8 Example 30 compound 8 BD2 3.55 6.92 (0.134, 0.129) 50.1 Example 31 compound 14 BD2 3.50 6.94 (0.134, 0.128) 48.8 Example 32 compound 19 BD2 3.49 6.98 (0.134, 0.130) 50.5 Example 33 compound 23 BD2 3.44 6.88 (0.134, 0.128) 47.8 Example 34 compound 26 BD2 3.54 6.84 (0.134, 0.127) 63.8 Comparative Example 1 BH1 BD1 3.78 4.89 (0.133, 0.156) 30.8 Comparative Example 2 BH2 BD1 3.80 4.90 (0.133, 0.156) 21.5 Comparative Example 3 BH3 BD1 3.76 5.11 (0.133, 0.160) 33.1 Comparative Example 4 BH4 BD1 3.77 5.08 (0.133, 0.161) 25.8 Comparative Example 5 BH5 BD1 3.89 6.05 (0.135, 0.138) 40.5 Comparative Example 6 BH6 BD1 3.88 6.12 (0.135, 0.138) 41.8 Comparative Example 7 BH7 BD1 4.99 3.12 (0.136, 0.142) 8.1 Comparative Example 8 BH8 BD1 3.81 5.42 (0.135, 0.139) 53.1 Comparative Example 9 BH9 BD1 3.69 5.12 (0.136, 0.142) 15.8 Comparative Example 10 BH10 BD1 3.85 5.01 (0.135, 0.138) 20.5 Comparative Example 11 BH11 BD1 3.80 4.98 (0.135, 0.139) 21.3 Comparative Example 12 BH12 BD1 3.88 5.23 (0.135, 0.138) 18.4 Comparative Example 13 BH13 BD1 3.82 5.11 (0.135, 0.138) 20.6 Comparative Example 14 BH14 BD1 3.88 5.10 (0.135, 0.139) 22.8 Comparative Example 15 BH5 BD2 3.95 6.23 (0.134, 0.122) 30.1 Comparative Example 16 BH8 BD2 3.98 5.70 (0.134, 0.122) 20.8 Comparative Example 17 BH10 BD2 4.02 5.71 (0.134, 0.121) 13.7 Comparative Example 18 BH13 BD2 3.96 6.01 (0.134, 0.121) 8.7

As shown in Table 3, the organic light emitting device using the compound represented by Formula 1 according to the present invention as a light emitting layer host exhibited excellent characteristics in terms of voltage, efficiency and stability of the organic light emitting device.

Specifically, the compound represented by Formula 1 includes a dibenzodioxin-based (dibenzodioxin, phenothiazine, or thianthrene) structure in an anthracene structure, and includes dibenzofuran in which a heterocycle is condensed. It is characterized by

As in Comparative Examples 1 to 4, the compound in which anthracene is introduced symmetrically into the dibenzodioxin-based structure has a fairly large molecular weight, and when used as a host of the light emitting layer, reduces the properties of the film and prevents the injection of the carrier. may cause interference. In addition, it shows a higher voltage than the device using the compound of the present invention, and shows the result of shifting the wavelength of the blue device to the red wavelength.

In addition, as in Comparative Examples 5 to 18, a compound in which anthracene is directly bonded to carbon 3 of dibenzofuran, or a compound that does not contain dibenzofuran in which a dibenzodioxin-based structure and a heterocyclic ring are condensed. The device exhibited lower voltage, efficiency, and/or lifetime than the compound of Formula 1 of the present invention.

Therefore, when the compound represented by Formula 1 according to the present invention is used as the light emitting layer host, the role of smooth hole injection into the light emitting layer can be controlled, and holes and electrons of the organic light emitting device are balanced according to the chemical structure, It can be seen that it exhibits excellent characteristics in terms of efficiency, driving voltage and stability.

1: Substrate
2: anode
3: hole injection layer
4: hole transport layer
5: Electron blocking layer
6: light emitting layer
7: hole blocking layer
8: electron transport layer
9: electron injection layer
10: cathode
11: capping layer

Claims (14)

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

In Formula 1,
X1 and X2 are the same as or different from each other, and each independently O; or S;
L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
one of R1 to R8 is bonded to L1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R9 is hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
Ar is represented by the following formula (A),
[Formula A]

In the formula A,
X3 is O; S; or CR101R102;
R101 and R102 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or an adjacent group bonded to each other to form a ring,
one of R11 to R14, Ra and Rb is bonded to L2, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group,
ra is an integer from 0 to 2, rb is an integer from 0 to 4,
When ra is 2, two Ra are the same as or different from each other, when rb is 2 or more, two or more Rb are the same as or different from each other,
n is an integer from 0 to 8,
When n is 2 or more, two or more R9 are the same as or different from each other. The method according to claim 1, wherein the formula A is a compound represented by any one of the following formulas A1 to A6:
[Formula A1] [Formula A2] [Formula A3]

[Formula A4] [Formula A5] [Formula A6]

In Formulas A1 to A6, the definition of X3 is the same as the definition in Formula A,
one of R11 to R14, Ra1, Ra2, and Rb1 to Rb4 is bonded to L2, the others are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group. The method according to claim 1, wherein Chemical Formula 1 is a compound represented by the following Chemical Formula 1-1 or 1-2:
[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2, the definitions of X1 to X3, L1, L2, R1 to R9, Ra, Rb, n, ra and rb are the same as the definitions in Formula 1 above,
R101 is hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group,
r101 is an integer from 0 to 4, r101' is an integer from 0 to 3, and when r101 and r101' are each 2 or more, two or more R101 are the same as or different from each other,
ra' is 0 or 1. The method according to claim 1, wherein Chemical Formula 1 is a compound represented by the following Chemical Formula 2-1 or 2-2:
[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2, definitions of X1, X2, L1, L2, R1 to R9, Ar, and n are the same as in Formula 1 above. The method according to claim 1, wherein L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a compound that is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms. The method according to claim 1, R1 to R8, the remainder not bonded to L1 are the same as or different from each other, and each independently hydrogen; or deuterium. The method according to claim 1, wherein one of R1 to R8 is bonded to L1, at least one of the groups not bonded to L1 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-30 N, O, or S-containing heterocyclic group compound. The compound of claim 1, wherein Formula 1 is at least 40% substituted with deuterium. The compound according to claim 1, wherein Formula 1 is represented by any one of the following compounds:

. anode; cathode; and at least one organic material layer provided between the anode and the cathode, wherein at least one of the organic material layers comprises the compound according to any one of claims 1 to 9. The organic light-emitting device of claim 10 , wherein the organic material layer includes an emission layer, and the emission layer includes the compound. The organic light-emitting device of claim 11 , wherein the emission layer includes the compound as a host and further includes a dopant. The organic light-emitting device of claim 10 , wherein 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, the hole transport layer, or the hole injection and transport layer includes the compound. The organic light-emitting device of claim 10 , wherein the organic material layer includes an electron transport layer, an electron injection layer, or an electron transport and injection layer, and the electron transport layer, the electron injection layer, or the electron transport and injection layer includes the compound. .

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