KR20230018160A - 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. An exemplary embodiment of the present specification provides a compound represented by chemical formula 1. 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 an organic light emitting device including the same {COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING 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 electrical energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often composed of a multi-layer structure composed of different materials to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows.

Development of new materials for the organic light emitting device as described above has been continuously demanded.

Korean Patent Publication No. 2015-0073064 Korean Patent Registration No. 10-1538534

In the present specification, a compound and an organic light emitting device including the same are provided.

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

[Formula 1]

In Formula 1,

R1 to R4 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,

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

Ar is represented by the following formula A,

[Formula A]

In the formula A,

X1 is O; S; or CR'R'';

Any one of R11 to R18 is bonded to L2, the rest not bonded 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,

However, when X1 is O or S, any one of R11, R13 to R16 and R18 is bonded to L2;

R' and R'' 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 bonded to adjacent groups to form a substituted or unsubstituted ring;

m is an integer from 1 to 4, and when m is 2 or more, 2 or more Ars are the same as or different from each other;

n1 and n2 are integers from 0 to 4, and when n1 and n2 are each 2 or more, 2 or more R1 and R2 are the same as or different from each other;

n3 is an integer from 0 to 3, and when n3 is 2 or more, two or more R3s are the same as or different from each other;

n4 is an integer from 0 to 8, and when n4 is 2 or more, two or more R4s are the same as or different from each other;

n2+n3 is 0 to 6.

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

The compounds described in this specification can be used as a material for an organic material layer of an organic light emitting device. The compound according to at least one exemplary embodiment may improve efficiency, low driving voltage, and/or lifetime characteristics of 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, luminescence, hole blocking, electron transport, or electron injection materials. In addition, compared to conventional organic light emitting devices, there are effects of low driving voltage, high efficiency, and/or long lifespan.

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

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

In the present specification, when a certain component is said to "include", it means that it may further include other components without excluding other components unless otherwise stated.

In this specification, when a member is said to be located “on” another member, this includes not only the case where a member is in contact with another member, but also the case where 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 of bonding to the chemical formula or compound.

In the present specification, the deuterium substitution rate of the compound is max. 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 integrated amount of the total peak using the integration ratio on 1H NMR can

In this specification, "energy level" means an energy level. Therefore, the energy level is interpreted as meaning the absolute value of the corresponding energy value. For example, that the energy level is low or deep means that the absolute value increases in a negative direction from the vacuum level.

In the present specification, HOMO (highest occupied molecular orbital) means a molecular orbital (highest occupied molecular orbital) in the region with the highest energy in a region where electrons can participate in bonding, and LUMO (lowest unoccupied molecular orbital) means a molecular orbital (lowest unoccupied molecular orbital) in which an electron has the lowest energy among the antibonding 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, a 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 (manufactured by 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 hydrogen atom is substituted, that is, a position where the substituent is substituted, and when two or more are substituted , Two or more substituents may be the same as or different from each other.

In this specification, the term "substituted or unsubstituted" means deuterium; halogen group; nitrile group (-CN); nitro group; hydroxy group; an alkyl group; cycloalkyl group; alkoxy group; phosphine oxide group; aryloxy group; Alkyl thioxy group; Arylthioxy group; an alkyl sulfoxy group; aryl sulfoxy groups; alkenyl group; silyl group; boron group; amine group; aryl group; Or substituted with one or two or more substituents selected from the group consisting of heterocyclic groups, or substituted with substituents in which two or more substituents among the above exemplified substituents are connected, or without 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.

In this specification, the term "substituted or unsubstituted" means deuterium; halogen group; nitrile group; nitro group; hydroxy 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, or is substituted with a substituent in which two or more substituents from among the above exemplified substituents are connected, or does not have any substituents.

In this specification, the term "substituted or unsubstituted" means deuterium; 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, or is substituted with a substituent in which two or more substituents from among 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 in 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 a chemical 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 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, but is not limited thereto. don't

In the present specification, the boron group may be represented by the chemical formula -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. The boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, but is not limited thereto.

In the present specification, the alkyl group may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of the alkyl group include 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 is 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 straight chain, branched chain or cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. 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, etc., but is not limited thereto. .

Alkyl groups, alkoxy groups, and substituents containing other alkyl moieties described herein include both straight-chain and branched 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 one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, etc., but is not limited thereto.

In the present specification, the alkynyl group is a substituent including a triple bond between carbon atoms and may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkynyl group is 2 to 20. According to another embodiment, the number of carbon atoms 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 number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and an adamantyl group, but are not limited thereto.

In the present specification, the amine group is -NH ₂ , and the amine group may be substituted with the aforementioned 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 one embodiment, the carbon number of the amine group is 1 to 20. According to one embodiment, the carbon number of the amine group is 1 to 10. Specific examples of the substituted amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, 9,9-dimethylfluorenylphenylamine group, pyridylphenylamine group, diphenylamine group, phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, dibenzofuranylphenylamine group, 9-methylanthracenylamine group, diphenylamine group, phenylnaphthylamine group, A ditolylamine group, a phenyltolylamine group, a diphenylamine group, and the like, but are 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 one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, etc. as a monocyclic aryl 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 no.

(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 with an aryl group. According to one 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. At this time, 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-dimethylfluorenyl group), and

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

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

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

In the present specification, the description of the aryl group described above may be applied to the aryl group among the arylthiooxy group and the arylsulfoxy group.

In the present specification, the heterocyclic group is a ring group containing one or more 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 one embodiment, the carbon number of the heterocyclic group is 2 to 30. According to one embodiment, the carbon number of the heterocyclic group is 2 to 20. 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, and a dibenzothiophene group. , A carbazole group, a benzocarbazole group, a naphthobenzofuran group, a benzonaphthothiophene group, an indenocarbazole group, and a triazinyl group, but are not limited thereto.

In the present specification, the heterocyclic group described above 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 heterocyclic ring is divalent.

In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups, "ring" refers to a hydrocarbon ring; or a heterocyclic ring.

The hydrocarbon ring may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, 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; A substituted or unsubstituted aliphatic heterocycle; A substituted or unsubstituted aromatic heterocycle; or to form a condensed ring thereof. The hydrocarbon ring means a ring composed of only carbon and hydrogen atoms. The heterocycle refers to a ring containing at least one selected from elements such as N, O, P, S, Si, and Se. In the present specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle and aromatic heterocycle may be monocyclic or polycyclic.

In the present specification, an aliphatic hydrocarbon ring is a non-aromatic ring and refers to a ring composed of only 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. Not limited to this.

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

In the present specification, an aliphatic heterocycle means an aliphatic ring containing one or more of heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine , Thiocane, etc., but are not limited thereto.

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

Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiments 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 introduces an indolocarbazole structure and a dibenzofuran, dibenzothiophene or fluorene ring into an anthracene structure, thereby exhibiting a low voltage when applied to a device, and indolocarbazole It exhibits excellent life characteristics from the stability of the molecular structure due to the cyclized form.

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

Therefore, 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 characteristics can be obtained.

Hereinafter, Formula 1 will be described in detail.

[Formula 1]

In Formula 1,

R1 to R4 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,

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

Ar is represented by the following formula A,

[Formula A]

In the formula A,

X1 is O; S; or CR'R'';

Any one of R11 to R18 is bonded to L2, the rest not bonded 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,

However, when X1 is O or S, any one of R11, R13 to R16 and R18 is bonded to L2;

R' and R'' 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 bonded to adjacent groups to form a substituted or unsubstituted ring;

m is an integer from 1 to 4, and when m is 2 or more, 2 or more Ars are the same as or different from each other;

n1 and n2 are integers from 0 to 4, and when n1 and n2 are each 2 or more, 2 or more R1 and R2 are the same as or different from each other;

n3 is an integer from 0 to 3, and when n3 is 2 or more, two or more R3s are the same as or different from each other;

n4 is an integer from 0 to 8, and when n4 is 2 or more, two or more R4s are the same as or different from each other;

n2+n3 is 0 to 6.

In one embodiment of the present specification, R1 to R4 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 one embodiment of the present specification, R1 to R4 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 having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; 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 one embodiment of the present specification, R1 to R4 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 having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; A substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group containing O, S or N having 2 to 30 carbon atoms.

In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; An alkylsilyl group having 1 to 20 carbon atoms unsubstituted or substituted with heavy hydrogen; An alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with heavy hydrogen; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen; an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen; or a heterocyclic group containing O, S or N having 2 to 30 carbon atoms unsubstituted or substituted with deuterium.

In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkylsilyl group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted cyclopentyl group; A substituted or unsubstituted cyclohexyl 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 fluorenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted furan group; A substituted or unsubstituted benzofuran group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted benzothiophene group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.

In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; trimethylsilyl group; methyl group; ethyl group; propyl group; butyl group; cyclopentyl group; cyclohexyl group; phenyl group; biphenyl group; terphenyl group; naphthyl group; dimethyl fluorenyl group; Diphenyl fluorenyl group; phenanthrenyl group; triphenylenyl group; furan group; Benzofuran group; Dibenzofuran group; thiophene group; Benzothiophene group; or a dibenzothiophene group, which is unsubstituted or substituted with deuterium.

In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; trimethylsilyl group; i-propyl group; t-butyl group; cyclopentyl group; phenyl group; or a naphthyl group, and the groups are unsubstituted or substituted with deuterium.

In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; trimethylsilyl group; i-propyl group; t-butyl group; cyclopentyl group; phenyl group; or a naphthyl group.

In one embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; trimethylsilyl group; i-propyl group; t-butyl group; cyclopentyl group; phenyl group; or a naphthyl group.

In one embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; trimethylsilyl group; i-propyl group; t-butyl group; cyclopentyl group; or a phenyl group.

In one embodiment of the present specification, R4 is hydrogen; heavy hydrogen; phenyl group; or a naphthyl group.

In one embodiment of the present specification, R4 is hydrogen; or a phenyl group.

In one embodiment of the present specification, R1 to R4 are each independently 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 are 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 are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.

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; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms, wherein the groups include deuterium; cyano group; an alkyl group having 1 to 20 carbon atoms; A cycloalkyl group having 3 to 30 carbon atoms; an aryl group having 6 to 30 carbon atoms; Or it is substituted or unsubstituted with a heterocyclic group having 2 to 30 carbon atoms.

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; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted divalent O, S or N-containing heterocyclic group having 2 to 30 carbon atoms.

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; an arylene group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen; or a divalent O, S or N-containing heterocyclic group having 2 to 30 carbon atoms 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 are each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted triphenylenylene group; A substituted or unsubstituted divalent furan group; A substituted or unsubstituted divalent benzofuran group; A substituted or unsubstituted divalent dibenzofuran group; A substituted or unsubstituted divalent thiophene group; A substituted or unsubstituted divalent benzothiophene group; A substituted or unsubstituted divalent dibenzothiophene group; Or a substituted or unsubstituted divalent carbazole 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; phenylene group; biphenylene group; Terphenylene group; naphthylene group; A phenanthrenylene group; triphenylenylene group; Divalent furan group; A divalent benzofuran group; Divalent dibenzofuran group; Divalent thiophene group; Divalent benzothiophene group; or a divalent dibenzothiophene group, which 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 are each independently a direct bond; phenylene group; biphenylene group; naphthylene group; A divalent benzofuran group; or a divalent thiophene group, which 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 are each independently a direct bond; phenylene group; biphenylene group; naphthylene group; A divalent benzofuran group; or a divalent thiophene group.

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

In one embodiment of the present specification, L1 is a direct bond; or a phenylene 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, L1 and L2 are independently substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ar is represented by Formula A below.

[Formula A]

In the formula A,

X1 is O; S; or CR'R'';

Any one of R11 to R18 is bonded to L2, the rest not bonded 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,

However, when X1 is O or S, any one of R11, R13 to R16 and R18 is bonded to L2;

R' and R'' 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 bonded to adjacent groups to form a substituted or unsubstituted ring.

In one embodiment of the present specification, X1 is O.

In one embodiment of the present specification, X1 is S.

In one embodiment of the present specification, X1 is CR'R''.

In one embodiment of the present specification, R11 or R18 binds to L2.

In one embodiment of the present specification, R13 or R16 binds to L2.

In one embodiment of the present specification, R14 or R15 binds to L2.

In one embodiment of the present specification, when X1 is CR'R'', R12 or R17 binds to L2.

In an exemplary embodiment of the present specification, any one of R11 to R18 is bonded to L2, and the rest not bonded 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, any one of R11 to R18 is bonded to L2, and the rest not bonded 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 having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; 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, any one of R11 to R18 is bonded to L2, and the rest not bonded 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 having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, any one of R11 to R18 is bonded to L2, and the rest not bonded to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; An alkylsilyl group having 1 to 20 carbon atoms unsubstituted or substituted with heavy hydrogen; An alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with heavy hydrogen; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen; an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen; or a heterocyclic group containing O, S or N having 2 to 30 carbon atoms unsubstituted or substituted with deuterium or an aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, any one of R11 to R18 is bonded to L2, and the rest not bonded to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkylsilyl group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted cyclopentyl group; A substituted or unsubstituted cyclohexyl 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 fluorenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted furan group; A substituted or unsubstituted benzofuran group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted benzothiophene group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.

In an exemplary embodiment of the present specification, any one of R11 to R18 is bonded to L2, and the rest not bonded to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyclopentyl group; cyclohexyl group; phenyl group; biphenyl group; terphenyl group; naphthyl group; dimethyl fluorenyl group; Diphenyl fluorenyl group; phenanthrenyl group; triphenylenyl group; furan group; Benzofuran group; Dibenzofuran group; thiophene group; Benzothiophene group; or a dibenzothiophene group, which is unsubstituted or substituted with deuterium or an aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, any one of R11 to R18 is bonded to L2, and the rest not bonded to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyclopentyl group; phenyl group; biphenyl group; naphthyl group; phenanthrenyl group; A thiophene group unsubstituted or substituted with a phenyl group; or a benzofuran group, and the groups are unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, any one of R11 to R18 is bonded to L2, and the rest not bonded to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyclopentyl group; phenyl group; biphenyl group; naphthyl group; phenanthrenyl group; A thiophene group substituted with a phenyl group; or a benzofuran group, and the groups are unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, any one of R11 to R18 is bonded to L2, and the rest not bonded to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyclopentyl group; phenyl group; biphenyl group; naphthyl group; phenanthrenyl group; A thiophene group substituted with a phenyl group; or a benzofuran group.

In an exemplary embodiment of the present specification, any one of R11 to R18 is bonded to L2, and the rest not bonded to L2 are the same as or different from each other, and each independently hydrogen; phenyl group; biphenyl group; naphthyl group; or a thiophene group substituted with a phenyl group.

In one embodiment of the present specification, any one of R11 to R18 is bonded to L2, and the rest not bonded to L2 are independently substituted or unsubstituted with deuterium.

In one embodiment of the present specification, R' and R'' 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 having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; 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, or bonded to an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms.

In one embodiment of the present specification, R' and R'' 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 having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or bonded to an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.

In one embodiment of the present specification, R' and R'' are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or bonded to an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R' and R'' are the same as or different from each other, and each independently an alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with heavy hydrogen; Or an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, or bonded to an adjacent group to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms substituted or unsubstituted with deuterium.

In one embodiment of the present specification, R' and R'' 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 bonded to adjacent groups to form a substituted or unsubstituted fluorene ring.

In an exemplary embodiment of the present specification, R' and R'' are the same as or different from each other, and each independently represents a methyl group unsubstituted or substituted with deuterium; Or a phenyl group unsubstituted or substituted with deuterium, or bonded to an adjacent group to form a fluorene ring unsubstituted or substituted with deuterium.

In one embodiment of the present specification, R' and R'' are the same as or different from each other, and each independently a methyl group; Or a phenyl group, or bonded to adjacent groups to form a fluorene ring.

In one embodiment of the present specification, R' and R'' are each independently unsubstituted or substituted with deuterium.

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

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

In one embodiment of the present specification, n1 and n2 are integers from 0 to 2.

In one embodiment of the present specification, n3 is an integer from 0 to 2.

In one embodiment of the present specification, n4 is an integer from 0 to 8.

In one embodiment of the present specification, n4 is 0 or 1.

In one embodiment of the present specification, n4 is 8.

In one embodiment of the present specification, Formula 1 is represented by any one of Formulas 1-1 to 1-6 below.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

In Formulas 1-1 to 1-6, the definitions of R1 to R4, L1, L2, Ar, m, and n1 to n4 are the same as those in Formula 1,

n2' is an integer from 0 to 3, and when n2' is 2 or more, 2 or more R2's are the same as or different from each other;

n3' is an integer from 0 to 2, and when n3' is 2, two R3's are the same as or different from each other.

In one embodiment of the present specification, Formula 1 is represented by any one of Formulas 2-1 to 2-3 below.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

In Formulas 2-1 to 2-3, the definitions of R1 to R4, L1, L2, R11 to R18 and n1 to n4 are the same as those in Formula 1,

Y1 is O; or S.

In one embodiment of the present specification, Formula 1 is represented by any one of Formulas 2-4 to 2-7 below.

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

[Formula 2-7]

In Formulas 2-4 to 2-7, the definitions of R1 to R4, L1, L2, R11 to R18, R', R″, and n1 to n4 are the same as those in Formula 1 above.

In one embodiment of the present specification, Formula 1 is represented by any one of Formulas 3-1 to 3-3 below.

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

In Formulas 3-1 to 3-3, the definitions of R1 to R3, L1, L2, Ar, m, and n1 to n3 are the same as those in Formula 1,

G1 to G8 are the same as or different from each other, and each independently hydrogen; or deuterium;

Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and each independently represents an aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and each independently a phenyl group; biphenyl group; or a naphthyl group.

In one embodiment of the present specification, Ar11 and Ar12 are independently substituted or unsubstituted with deuterium.

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

In one 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 an exemplary embodiment of the present specification, R1 to R4 are the same as or different from each other, and each may be independently substituted with deuterium.

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

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

In one embodiment of the present specification, R11 to R18 are the same as or different from each other, and each may be independently substituted with deuterium.

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

The compound is unsubstituted or substituted with deuterium.

The core structure of the compound represented by Formula 1 according to an exemplary embodiment of the present specification may be prepared as in the preparation example 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 may be synthesized by introducing various substituents into the core structure of the compound represented by Formula 1. 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 above structure.

In addition, the present specification provides an organic light emitting device including the aforementioned compound.

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

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

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

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, or 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 includes 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. may have a structure that includes However, the structure of the organic light emitting device of the present specification is not limited thereto and may include fewer or more 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 comprises a compound represented by the above-described formula (1). can 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 hole injection layer may include the compound represented by Chemical Formula 1.

In one 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 described above. It may include the compound represented by Formula 1.

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-described formula (1) compounds may be included.

In one 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 one 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 above.

In one 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 one 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 blue host.

In one 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 dopant.

In one 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 Chemical Formula 1 as a host.

According to one 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 Chemical 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 Chemical Formula 1 as a host.

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

At this time, the dopant is a phosphorescent material such as (4,6-F2ppy) ₂ Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distryarylene (DSA), PFO-based polymer, PPV-based Fluorescent materials such as polymers, anthracene-based compounds, pyrene-based compounds, and boron-based compounds may be used, but are 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 Chemical Formula 1 described above.

In the organic light emitting device according to one embodiment of the present specification, the light emitting layer further includes a fluorescent dopant or a phosphorescent dopant. At this time, the dopant in the light emitting layer is included in 1 part by weight to 50 parts by weight based on 100 parts by weight of the host.

In one 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, according to one example 50 Å to 400 Å, and according to another example 100 Å to 400 Å is Å.

In the organic light emitting device according to an 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 includes a light emitting layer, and the light emitting layer includes the compound represented by Chemical Formula 1 as a host and may further include an additional host.

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

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

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

In one embodiment of the present specification, the light emitting layer including the compound represented by Chemical Formula 1 is blue.

According to one example, the amount 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 sum of the host and the dopant of the light emitting 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 one embodiment of the present specification, the organic material layer includes the compound, and the compound has a band gap energy of 2.9 eV or more.

The organic light emitting device of the present specification may further include one or more organic material layers 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 one 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 Chemical Formula 1.

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

In one embodiment of the present specification, the two or more organic material layers may be two or more 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 one embodiment of the present specification, the organic material layer includes two or more light emitting layers, and at least one of the two or more light emitting layers includes the compound represented by Chemical Formula 1. Specifically, in one embodiment of the present specification, the compound represented by Formula 1 may be included in one layer of the two or more light emitting layers, and may be included in each of the two or more light emitting layers.

In one 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 Chemical Formula 1. Specifically, in one embodiment of the present specification, the compound represented by Formula 1 may be included in one layer of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.

In addition, in one 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 as or different from each other.

When the organic material layer including the compound represented by Chemical 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, and for example, a metal or a metal complex may be used. For example, the electron transport layer including the compound represented by Chemical Formula 1 may further include lithium quinolate (LiQ).

In one 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 Chemical Formula 1. Specifically, in one embodiment of the present specification, the compound represented by Chemical 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 one embodiment of the present specification, the organic material layer further includes a hole injection layer or a hole transport layer containing a compound containing an arylamine group, a carbazolyl group, or a benzocarbazolyl group in addition to the organic material layer containing the compound represented by Formula 1 can include

In one 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 one embodiment of the present specification, the organic light emitting device may be an organic light emitting device of an inverted type 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, and materials known in the art may be used for the electron blocking layer.

The organic light emitting device may have, for example, a stacked structure as described below, 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

(18) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode / capping layer

The structure of the organic light emitting device 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 this structure, the compound may be included in the light emitting layer (6).

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

For example, the organic light emitting device according to the present specification uses a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a metal or conductive metal oxide or an alloy thereof on a substrate. It is prepared by depositing an anode, forming 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 thereon, and then depositing a material that can be used as a cathode thereon. It 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, and an electron transport and injection layer, but is not limited thereto and may have a single layer structure. can In addition, the organic material layer can be formed by a solvent process other than a deposition method using various polymer materials, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or a thermal transfer method. Can be made in layers.

The anode is an electrode for injecting holes, and the anode material is preferably a material having a high work function so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO: Al or SnO ₂ : Sb; 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 it is preferable that the cathode material is a material having a small work function so as to easily inject electrons 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; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection layer is a layer that serves to facilitate the injection of holes from the anode to the light emitting layer, and the hole injection material is a material that can receive holes well from the anode at a low voltage, HOMO (highest occupied) of the hole injection material 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 materials, hexanitrilehexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene-based organic materials. of organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto. The hole injection layer may have a thickness of 1 nm to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage in preventing the hole injection characteristic from deteriorating, and if it is 150 nm or less, the thickness of the hole injection layer is too thick to increase the driving voltage to improve the movement of holes. There are advantages to avoiding this.

In one embodiment of the present specification, the hole injection layer may include at least one N-containing polycyclic compound including a cyano group or an amine compound including a carbazole group. In this case, the N-containing polycyclic compound may be 1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile (HATCN). According to one example, the hole transport layer may include the above compounds alone or in combination of two or more. According to another example, the HATCN may be deposited and used as the first hole transport layer, and the amine compound containing the carbazole group may be deposited thereon and used as the second hole transport layer.

The hole transport layer may play a role of facilitating hole transport. As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer, and a material having high hole mobility is suitable. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.

In one embodiment of the present specification, the hole transport layer may include an amine compound containing a carbazole group.

A hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.

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

In one embodiment of the present specification, the electron blocking layer may include an amine compound including a carbazole group. According to one example, the compound may have a carbazole group and an amine group linked to an ortho-biphenylene group.

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 compound of Formula 1 described above; 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; Polyfluorene, rubrene, etc., but are not limited thereto.

A host material for the light emitting layer includes a condensed aromatic ring derivative or a compound containing a hetero ring. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

When the light emitting layer emits red light, PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonateiridium), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium), PQIr (tris (1-phenylquinoline) iridium) are used as light emitting dopants. ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq ₃ (tris(8-hydroxyquinolino)aluminum), but is not limited thereto. When the light emitting layer emits green light, a phosphorescent material 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 light emitting dopant. However, it is not limited thereto. When the light emitting layer emits blue light, as the light emitting dopant, a phosphorescent material such as (4,6-F2ppy) ₂ Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distryarylene (DSA), Fluorescent materials such as PFO-based polymers and PPV-based polymers may be used, but are not limited thereto.

In one embodiment of the present specification, the light emitting layer may include the compound according to the present invention as a host, and may include a pyrene compound having an amine group substituted or a polycyclic compound including boron as a dopant. The host and the dopant may be included in an appropriate weight ratio, and according to one example, the host and the dopant may be included in a weight ratio of 100:1 to 100:10, respectively.

The hole blocking layer is a layer that blocks the flow of holes from the light emitting layer to the cathode and controls the flow of electrons into the light emitting layer to control the overall performance of the device. As the hole blocking material, a compound having an ability to prevent the inflow of holes from the light emitting layer to the cathode and control electrons injected into the light emitting layer or the light emitting material is preferable. An appropriate material may be used as the hole blocking material depending on the configuration of the organic material layer used in the device. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.

In one embodiment of the present specification, the hole blocking layer may include a compound having a structure in which an N-containing ring is directly or through a linker connected to a spiro fluorene xanthene (spiro [fluorene-9,9'-xanthene]) structure. there is.

The electron transport layer may serve to facilitate electron transport. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable. Specific examples include Al complexes of the aforementioned compounds or 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 in preventing deterioration of electron transport properties, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent an increase in driving voltage to improve electron movement. There are advantages that can be

In one embodiment of the present specification, the electron transport layer may include a compound including an N-containing ring and CN, and may further include an n-type dopant or an organometallic compound. According to one example, the n-type dopant or organometallic compound may be LiQ, and the compound represented by Formula 1 of the present invention and the n-type dopant (or organometallic compound) have a ratio of 2:8 to 8:2, such as 4: It may be included in a weight ratio of 6 to 6:4.

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

In one embodiment of the present specification, the electron injection layer may include lithium fluoride (LiF).

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)( There are o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato)gallium. Not limited to this.

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

The organic light emitting device according to the present specification may be included in and used in various electronic devices. For example, the electronic device may be a display panel, a touch panel, a solar module, a lighting device, and the like, but is not limited thereto.

Hereinafter, examples will be described in detail in order to specifically describe the present specification. However, the embodiments according to the present specification may be modified in many different forms, and the scope of the present application is not construed as being limited to the embodiments detailed below. The embodiments of the present application are provided to more completely explain the present specification to those skilled in the art.

Preparation Example 1 (Synthesis of A1-1 to A1-4 and A2-1 to A2-6)

SM1 (1eq) and SM2 (2eq) were dissolved in dimethylacetamide (excess), and potassium carbonate (1eq) and copper (0.1eq) were added, followed by reflux stirring for 12 hours. After confirming the completion of the reaction, it was cooled to room temperature, a saturated sodium chloride aqueous solution (brine) was added to the reactant, extracted with chloroform and water, and the solvent was removed by reduced pressure distillation. Thereafter, the above formulas A1 and A2 (A1-1 to A1-4 and A2-1 to A2-6 in Table A) were prepared by column with ethyl acetate and hexane.

A1-1 to A1-4 and A2-1 to A2-6 were synthesized in the same manner except for changing SM1 and SM2 as shown in Table A in the synthesis method of Chemical Formulas A1 and A2.

Preparation Example 2 (Synthesis of B1 to B10)

Formula A1 or A2 (1eq) (SM1), palladium acetate (0.3eq), and tricyclohexylphosphine (0.6eq) synthesized in Preparation Example 1 were added to dimethylacetamide (excess) and stirred under reflux for 5 hours. After confirming the completion of the reaction, it was cooled to room temperature, water was added, and the resulting solid was filtered, and the solid was dissolved in toluene, extracted, and columned with ethyl acetate and hexane to prepare Formula B (B1 to B10 in Table B below).

B1 to B10 were synthesized in the same manner except for changing SM1 as shown in Table B in the synthesis method of Formula B above.

Preparation Example 3 (Synthesis of Compounds C1 to C2)

Formula B (1eq) (SM1) and SM2 (1.05eq) synthesized in Preparation Example 2 were added to tetrahydrofuran (excess), and then 2M potassium carbonate aqueous solution (30 volume ratio compared to THF) was added, and tetrakistriphenyl - After adding phosphinopalladium (2 mol%), the mixture was heated and stirred for 10 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium carbonate aqueous solution was removed to separate the layers. After confirming the completion of the reaction, the temperature was extracted to room temperature to remove the solvent and purified by recrystallization using chloroform and ethanol to prepare Formula C (C1 to C2 in Table C below).

Synthesis of Chemical Formula C (C1 to C2) in [Table C] was performed in the same manner except that SM1 and SM2 were changed as follows.

Preparation Example 4 (Synthesis of Compounds D1 to D11)

SM 1 (1eq) and SM2 (1.3eq) corresponding to formulas B and C synthesized in Preparation Example 2 or 3 were added to 1,4-dioxane (12 times <mass ratio> compared to SM1) and potassium acetate (3eq) ) was added to stir and reflux. Palladium acetate (0.02eq) and tricyclohexylphosphine (0.04eq) were stirred in 1,4-dioxane for 5 minutes, then added, and after 2 hours, the reaction was confirmed and cooled to room temperature. After adding ethanol and water, the mixture was filtered and purified by recrystallization with ethyl acetate and ethanol to prepare Formula D (D1 to D11 in Table D).

D1 to D11 were synthesized in the same manner except for changing SM1 and SM2 as follows in the synthesis method of Chemical Formula D.

Preparation Example 5 (Synthesis of Compounds 1 to 21)

Formula D (1eq) (SM1) and SM2 (1.05eq) synthesized in Preparation Example 4 were added to tetrahydrofuran (excess), and then 2M potassium carbonate aqueous solution (30 volume ratio compared to THF) was added, and tetrakistriphenyl - After adding phosphinopalladium (2 mol%), the mixture was heated and stirred for 10 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium carbonate aqueous solution was removed to separate the layers. After confirming the completion of the reaction, the temperature was extracted at room temperature, the solvent was removed, and the mixture was purified by recrystallization using toluene to prepare compounds 1 to 21 of Table 1 below.

Synthesis of compounds 1 to 21 in [Table 1] was performed in the same manner except that SM1 and SM2 were changed as follows.

Preparation Example 6 (Synthesis of Compounds 22 to 24)

The reactant (1eq) and Trifluoromethanesulfonic acid (cat.) were put into C ₆ D ₆ (10 to 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, stirred for 30 minutes, and trimethylamine (excess) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and chloroform. The extract was dried over MgSO ₄ , recrystallized by heating with toluene, and Compounds 22 to 24 in [Table 2] were obtained.

[Each product has a different degree of deuterium substitution depending on the reaction time, and the substitution rate is determined according to the maximum m/z (M+) value]

Substitution of deuterium for the above product was referred to Korean Patent Registration No. 10-1538534.

<Example 1> Preparation of OLED

A substrate on which 70/1000/70 Å of ITO/Ag/ITO was deposited as an anode 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. Detergent was a Fischer Co. product, and distilled water was a Millipore Co. product. Secondary filtered distilled water was used as the filter of the product. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed in the order of isopropyl alcohol, acetone, and methanol solvent, and dried.

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 host compound 1 and dopant compound BD1 (2% by weight based on 100% by weight of the total host and dopant) synthesized in Preparation Example 5 were mixed with 360 Å. A light emitting layer was formed by vacuum deposition. Thereafter, 50 Å of ET1 was deposited to form a hole blocking layer, and a compound ET2 and Liq were mixed in a weight ratio of 7:3 to form an electron transport layer having a thickness of 250 Å. After sequentially forming a film of 50 Å thick lithium fluoride (LiF) as an electron injection layer, 200 Å of magnesium and silver (1:4 weight ratio) was formed as a cathode, and then 600 Å of CP1 was deposited to complete the device. In the above process, the deposition rate of the organic material was maintained at 1 Å/sec.

<Examples 2 to 38 and Comparative Examples 1 to 14>

A device was manufactured in the same manner as in Example 1, except that the compounds of Table 3 were used instead of Compound 1 and Compound BD1. The compounds of BH1 to BH12 used in Table 3 are as follows.

With respect to the organic light emitting devices prepared in the above Examples and Comparative Examples, driving voltage, luminous efficiency and color coordinates were measured at a current density of 20 mA/cm ² , and 95% of the initial luminance at a current density of 20 mA/cm ² The time to become (T ₉₅ ) was measured. The results are shown in Table 3 below.

Experimental example
20 mA/cm2 host dopant Voltage (V)
(@20mA/cm ² ) Cd/A
(@20mA/cm ² ) color coordinates
(x,y) life span
(T95, h)
(@20mA/cm ² ) Example 1 compound 1 BD1 3.38 6.58 (0.135, 0.138) 52.8 Example 2 compound 2 BD1 3.36 6.63 (0.134, 0.137) 53.4 Example 3 compound 3 BD1 3.53 6.66 (0.134, 0.148) 55.4 Example 4 compound 4 BD1 3.52 6.65 (0.134, 0.137) 59.1 Example 5 compound 5 BD1 3.53 6.54 (0.136, 0.139) 52.8 Example 6 compound 6 BD1 3.46 6.55 (0.135, 0.138) 53.9 Example 7 compound 7 BD1 3.50 6.59 (0.135, 0.138) 54.2 Example 8 compound 8 BD1 3.39 6.54 (0.134, 0.137) 55.2 Example 9 compound 9 BD1 3.55 6.55 (0.135, 0.141) 54.5 Example 10 compound 10 BD1 3.53 6.58 (0.134, 0.137) 55.0 Example 11 compound 11 BD1 3.39 6.59 (0.134, 0.137) 53.8 Example 12 compound 12 BD1 3.48 6.43 (0.134, 0.145) 54.4 Example 13 compound 13 BD1 3.51 6.51 (0.135, 0.138) 54.6 Example 14 compound 14 BD1 3.38 6.58 (0.134, 0.137) 56.1 Example 15 compound 15 BD1 3.42 6.53 (0.134, 0.137) 57.2 Example 16 compound 16 BD1 3.49 6.49 (0.134, 0.144) 55.9 Example 17 compound 17 BD1 3.48 6.60 (0.135, 0.138) 53.4 Example 18 compound 18 BD1 3.44 6.58 (0.135, 0.138) 53.9 Example 19 compound 19 BD1 3.45 6.55 (0.135, 0.138) 56.1 Example 20 compound 20 BD1 3.48 6.47 (0.134, 0.137) 51.9 Example 21 compound 21 BD1 3.42 6.51 (0.134, 0.140) 54.5 Example 31 compound 22 BD1 3.39 6.57 (0.135, 0.138) 73.8 Example 32 compound 23 BD1 3.37 6.62 (0.134, 0.137) 74.3 Example 33 compound 24 BD1 3.50 6.59 (0.135, 0.121) 75.1 Example 34 compound 2 BD2 3.50 7.02 (0.134, 0.122) 48.3 Example 35 compound 3 BD2 3.68 7.23 (0.134, 0.132) 47.0 Example 36 compound 4 BD2 3.66 7.20 (0.134, 0.123) 50.0 Example 37 compound 16 BD2 3.59 7.14 (0.134, 0.130) 46.8 Example 38 compound 17 BD2 3.65 7.18 (0.135, 0.122) 46.9 Comparative Example 1 BH1 BD1 3.99 5.40 (0.134, 0.138) 30.8 Comparative Example 2 BH2 BD1 3.88 3.30 (0.134, 0.138) 32.7 Comparative Example 3 BH3 BD1 3.84 5.23 (0.134, 0.138) 33.9 Comparative Example 4 BH4 BD1 3.85 5.30 (0.134, 0.137) 35.4 Comparative Example 5 BH5 BD1 3.90 5.33 (0.134, 0.137) 30.4 Comparative Example 6 BH6 BD1 3.97 5.41 (0.134, 0.137) 33.1 Comparative Example 7 BH7 BD1 3.85 5.38 (0.134, 0.137) 31.8 Comparative Example 8 BH8 BD1 3.95 5.23 (0.134, 0.138) 30.1 Comparative Example 9 BH9 BD1 3.90 5.39 (0.134, 0.137) 32.3 Comparative Example 10 BH10 BD1 3.87 5.44 (0.134, 0.138) 30.8 Comparative Example 11 BH11 BD1 3.80 6.00 (0.134, 0.138) 50.1 Comparative Example 12 BH12 BD1 3.79 5.89 (0.134, 0.123) 48.1 Comparative Example 13 BH1 BD2 4.23 5.88 (0.134, 0.123) 23.8 Comparative Example 14 BH2 BD2 4.09 5.77 (0.134, 0.123) 22.4

As described in Table 1 above, in the case of the organic light emitting devices of Examples 1 to 38 using the compound represented by Formula 1 of the present invention, the voltage, efficiency and / or lifespan exhibiting superior characteristics than Comparative Examples 1 to 14 You can check.

Specifically, the compound represented by Formula 1 of the present invention has a structure in which an indolocarbazole structure and a group represented by Formula A are bonded to an anthracene structure. When Formula A has a dibenzofuran or dibenzothiophene structure, it balances the movement of holes and electrons in the host compound, and when it has a fluorene structure, the compound exhibits excellent low voltage characteristics.

On the other hand, Comparative Example 1 uses a structure in which a dibenzofuran group and an aryl group are bonded to an anthracene structure, and Comparative Examples 2 to 10, 13 and 14 use a structure in which an indolocarbazole structure and an aryl group are bonded to an anthracene structure. . In the case of Comparative Examples 1 to 10, 13 and 14, voltage, efficiency and lifetime characteristics are significantly lowered than in the case of using a compound in which an indolocarbazole group and a group represented by Formula A are simultaneously bonded to an anthracene structure as in the present invention. can confirm that

In Comparative Examples 11 and 12, compounds in which position 3 of dibenzofuran is bonded to anthracene are used, and the bonding positions of dibenzofuran and dibenzothiophene are different from those of the compound of the present invention. From the difference in the binding position, it can be confirmed that the voltage, efficiency and lifetime of Comparative Examples 11 and 12 are significantly reduced compared to the case where the compound of the present invention is used.

From the above results, it can be confirmed that by using the compound according to the present invention, it is possible to control the role of smooth hole injection into the light emitting layer, and exhibits excellent characteristics in terms of efficiency, driving voltage and lifetime from the balance of holes and electrons according to the chemical structure. there is.

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 Formula 1 below:
[Formula 1]

In Formula 1,
R1 to R4 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,
L1 and L2 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
Ar is represented by the following formula A,
[Formula A]

In the formula A,
X1 is O; S; or CR'R'';
Any one of R11 to R18 is bonded to L2, the rest not bonded 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,
However, when X1 is O or S, any one of R11, R13 to R16 and R18 is bonded to L2;
R' and R'' 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 bonded to adjacent groups to form a substituted or unsubstituted ring;
m is an integer from 1 to 4, and when m is 2 or more, 2 or more Ars are the same as or different from each other;
n1 and n2 are integers from 0 to 4, and when n1 and n2 are each 2 or more, 2 or more R1 and R2 are the same as or different from each other;
n3 is an integer from 0 to 3, and when n3 is 2 or more, two or more R3s are the same as or different from each other;
n4 is an integer from 0 to 8, and when n4 is 2 or more, two or more R4s are the same as or different from each other;
n2+n3 is 0 to 6. The compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-6:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

In Formulas 1-1 to 1-6, the definitions of R1 to R4, L1, L2, Ar, m, and n1 to n4 are the same as those in Formula 1,
n2' is an integer from 0 to 3, and when n2' is 2 or more, 2 or more R2's are the same as or different from each other;
n3' is an integer from 0 to 2, and when n3' is 2, two R3's are the same as or different from each other. The compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 2-1 to 2-3:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

In Formulas 2-1 to 2-3, the definitions of R1 to R4, L1, L2, R11 to R18 and n1 to n4 are the same as those in Formula 1,
Y1 is O; or S. The compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 2-4 to 2-7:
[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

[Formula 2-7]

In Formulas 2-4 to 2-7, the definitions of R1 to R4, L1, L2, R11 to R18, R', R″, and n1 to n4 are the same as those in Formula 1 above. The method according to claim 1, wherein the L1 and L2 are the same as or different from each other, each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted triphenylenylene group; A substituted or unsubstituted divalent furan group; A substituted or unsubstituted divalent benzofuran group; A substituted or unsubstituted divalent dibenzofuran group; A substituted or unsubstituted divalent thiophene group; A substituted or unsubstituted divalent benzothiophene group; A substituted or unsubstituted divalent dibenzothiophene group; Or a compound that is a substituted or unsubstituted divalent carbazole group. The method according to claim 1, wherein R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; trimethylsilyl group; i-propyl group; t-butyl group; cyclopentyl group; phenyl group; Or a compound that is a naphthyl group. The method according to claim 1, wherein R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; An alkylsilyl group having 1 to 20 carbon atoms unsubstituted or substituted with heavy hydrogen; An alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with heavy hydrogen; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen; an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen; Or a heterocyclic group containing O, S or N having 2 to 30 carbon atoms unsubstituted or substituted with deuterium,
Wherein L1 and L2 are the same as or different from each other, and are each independently a direct bond; an arylene group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen; Or a divalent O, S or N-containing heterocyclic group having 2 to 30 carbon atoms unsubstituted or substituted with deuterium,
The rest of R11 to R18 not bonded to L2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; An alkylsilyl group having 1 to 20 carbon atoms unsubstituted or substituted with heavy hydrogen; An alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with heavy hydrogen; A cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen; an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen; Or a heterocyclic group containing O, S or N having 2 to 30 carbon atoms unsubstituted or substituted with deuterium or an aryl group having 6 to 30 carbon atoms,
Wherein R' and R'' are the same as or different from each other, and are each independently an alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with deuterium; Or an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, or bonded to an adjacent group to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms substituted or unsubstituted with deuterium,
The compound wherein m is 1. 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:

The compound is unsubstituted or substituted with deuterium. anode; cathode; and one or more organic material layers provided between the anode and the cathode, wherein at least one of the organic material layers includes 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 a light emitting layer, and the light emitting layer includes the compound. The organic light emitting device of claim 11, wherein the light emitting 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, and the electron transport and injection layer include the compound. .

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