KR20210080655A - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a compound of chemical formula 1, and an organic light emitting device including the same. The compound according to an embodiment of the present specification can be used as a material for an organic material layer of the organic light emitting device, and by using the same, it is possible to improve efficiency, lower driving voltage and/or improve lifespan characteristics in the organic light emitting device.

Description

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

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

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

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

US Patent Application Publication No. 2004-0251816

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

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

[Formula 1]

In Formula 1,

A1 is a direct bond; O; or S;

R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may combine with each other to form a ring substituted or unsubstituted with -L1-Ar1,

R3 to R10 are the same as or different from each other, and each independently hydrogen; or -L1-Ar1;

When R1 and R2 are combined with each other to form a ring substituted with -L1-Ar1, R3 to R10 are hydrogen;

wherein R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or when combined with each other to form an unsubstituted ring, any one of R3 to R10 is -L1-Ar1, the rest is hydrogen;

L1 is a direct bond; Or a substituted or unsubstituted arylene group,

Ar1 is a group represented by any one of the following formulas 2-1 to 2-7,

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

[Formula 2-7]

In Formulas 2-1 to 2-7,

* is a site bonded to L1 of Formula 1,

Y1 is a group represented by the following formula (3),

At least one of X1 to X3 is N, the rest is CH,

At least one of X4 and X5 is N, the other is CH,

At least one of X6 and X7 is N, the other is CH,

X8 is N, Z1 is N or C, or X8 is CH, Z1 is N,

X9 is N, Z2 is N or C, or X9 is CH, Z2 is N,

X10 is N, Z3 is N or C, or X10 is CH, Z3 is N,

X11 is N, Z4 is N or C, or X11 is CH, Z4 is N,

Y2 to Y8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

y3 is an integer of 1 to 4, and when y3 is 2 or more, 2 or more Y3 are the same as or different from each other,

y4 is 1 or 2, and when y4 is 2, two Y4 are the same as or different from each other,

y5 is an integer of 1 to 4, and when y5 is 2 or more, 2 or more Y5 are the same as or different from each other,

y6 is an integer of 1 to 4, and when y6 is 2 or more, 2 or more Y6 are the same as or different from each other,

y7 is 1 or 2, and when y7 is 2, two Y7 are the same as or different from each other,

y8 is 1 or 2, and when y8 is 2, two Y8s are the same as or different from each other,

[Formula 3]

In Formula 3,

은 상기 화학식 2-1 내지 2-5 중 어느 하나에 결합되는 부위이며,

is a site bound to any one of Formulas 2-1 to 2-5,

L2 is a direct bond; Or a substituted or unsubstituted arylene group,

one to four of Q1 to Q5 are N, the others are CR,

At least one of R is a substituted or unsubstituted alkyl group, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted aryl group.

In addition, the present specification is a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one organic material layer includes the compound.

The compound according to an exemplary embodiment of the present specification may be used as a material for an organic material layer of an organic light emitting device, and by using the compound, it is possible to improve efficiency, low driving voltage and/or lifespan characteristics in an organic light emitting device.

1 to 3 show examples of an organic light emitting device according to an exemplary embodiment of the present specification.

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

The present specification provides a compound represented by Formula 1 above.

The compound according to the exemplary embodiment of the present specification has a non-linear structure, and thus it is possible to improve efficiency, low driving voltage, and lifespan characteristics in an organic light emitting device. In addition, in the structure of the compound represented by Formula 1, since the substituent -L-Ar1 has a substituent having an electron depletion structure, the dipole moment of the molecule can be increased. The efficiency and lifespan of the organic light-emitting device including the compound represented by Chemical Formula 1 can be improved by smoothly controlling the electron mobility when manufacturing the device. In addition, when R1 and R2 of Formula 1 form a ring, the steric hindrance due to the spiro-type structure prevents crystallization occurring during film formation, and maintains high thermal stability, which has a very limited effect even at a high deposition temperature. . Accordingly, in the organic light emitting device including the compound according to the exemplary embodiment of the present specification, it is possible to improve efficiency, lower driving voltage, and improve lifespan characteristics.

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

는 연결되는 부위를 의미한다.In this specification,

means the part to be connected.

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

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

또는

의 치환기가 될 수 있다. 또한, 3개의 치환기가 연결되는 것은 (치환기 1)-(치환기 2)-(치환기 3)이 연속하여 연결되는 것뿐만 아니라, (치환기 1)에 (치환기 2) 및 (치환기 3)이 연결되는 것도 포함한다. 예컨대, 페닐기, 나프틸기 및 이소프로필기가 연결되어,

,

또는

의 치환기가 될 수 있다. 4 이상의 치환기가 연결되는 것에도 전술한 정의가 동일하게 적용된다.In the present specification, that two or more substituents are connected means that the hydrogen of any one substituent is connected with another substituent. For example, when two substituents are connected, a phenyl group and a naphthyl group are connected.

or

may be a substituent of In addition, the connection of three substituents means that (substituent 1)-(substituent 2)-(substituent 3) is continuously connected, as well as (substituent 2) and (substituent 3) are connected to (substituent 1). include For example, a phenyl group, a naphthyl group and an isopropyl group are connected,

,

or

may be a substituent of The above definition applies equally to the case where 4 or more substituents are connected.

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

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

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

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. may be It is not limited.

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 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but is not limited thereto.

In the present specification, the haloalkyl group means that at least one halogen group is substituted for hydrogen in the alkyl group in the definition of the alkyl group.

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

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

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it is C10-30. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalene group, a perylene group, a chrysene group, a fluorene group, and the like, but is not limited thereto.

In the present specification, the fluorene group may be substituted, and adjacent groups may combine with each other to form a ring.

,

,

,

,

,

,

및

등이 있으나, 이에 한정되지 않는다.When the fluorene group is substituted,

,

,

,

,

,

,

and

and the like, but is not limited thereto.

As used herein, "adjacent" group means a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted. can For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups.

In the present specification, the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridine group. , pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benz Oxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine group, phenanthridine group, phenanthroline group, isoxazole group, thia Diazole group, dibenzofuran group, dibenzosilol group, phenoxanthine group (phenoxathiine), phenoxazine group (phenoxazine), phenothiazine group (phenothiazine), dihydroindenocarbazole group, spirofluorene xanthene group and spirofluorene There is a thioxanthene group, but is not limited thereto.

In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, or the like. Examples of the above-described alkyl group may be applied to the alkyl group of the alkylsilyl group, the examples of the above-described aryl group may be applied to the aryl group of the arylsilyl group, and the heteroaryl group of the heteroarylsilyl group is an example of the heteroaryl group. can be applied.

In the present specification, the boron group _{may be -BR 100} R ₁₀₁ , wherein R ₁₀₀ and R ₁₀₁ are the same or different, and each independently hydrogen; heavy hydrogen; halogen; nitrile group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms. Specifically, the boron group includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

In the present specification, the amine group is -NH ₂ , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group from the group consisting of may be selected, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, and a 9-methyl-anthracenylamine group. , diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group; N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthre nylfluorenylamine group, N-biphenylfluorenylamine group, and the like, but is not limited thereto.

In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group. The alkyl group and the aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and the aryl group described above.

In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group. The aryl group and the heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the above-described aryl group and heteroaryl group.

In the present specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group. The alkyl group and the heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the above-described alkyl group and heteroaryl group.

In the present specification, examples of the alkylamine group include a substituted or unsubstituted monoalkylamine group, or a substituted or unsubstituted dialkylamine group. The alkyl group in the alkylamine group may be a straight-chain or branched alkyl group. The alkylamine group including two or more alkyl groups may include a straight-chain alkyl group, a branched-chain alkyl group, or a straight-chain alkyl group and a branched alkyl group at the same time. For example, the alkyl group in the alkylamine group may be selected from the examples of the alkyl group described above.

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

In the present specification, the meaning of "adjacent two of the substituents combine with each other to form a ring" means a substituted or unsubstituted hydrocarbon ring by bonding with adjacent groups; Or it means to form a substituted or unsubstituted heterocyclic ring.

In the present specification, in a substituted or unsubstituted ring formed by bonding to each other, "ring" is a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocyclic ring.

In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon and an aliphatic hydrocarbon, and may be selected from among the examples of the cycloalkyl group or the aryl group, except for those not monovalent.

In the present specification, the heterocycle includes atoms other than carbon and one or more heteroatoms, and specifically, the heterocyclic atoms may include one or more atoms selected from the group consisting of O, N, Se and S, and the like. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and the aromatic heterocycle may be selected from among the examples of the heteroaryl group except that it is not monovalent.

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

In the present specification, the arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.

In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the heteroaryl group described above may be applied.

Hereinafter, the compound represented by Formula 1 will be described in detail.

According to an exemplary embodiment of the present specification, in Formula 1, wherein R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 6 to 30 carbon atoms, or combine with each other to form a hydrocarbon ring substituted or unsubstituted with -L1-Ar1.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted C1-C20 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 6 to 20 carbon atoms, or combine with each other to form an aromatic hydrocarbon ring substituted or unsubstituted with -L1-Ar1.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heteroaryl group having 6 to 30 carbon atoms, or combine with each other to form a hydrocarbon ring unsubstituted or substituted with -L1-Ar1.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 30 carbon atoms; Or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or combined with each other to form an aromatic hydrocarbon ring unsubstituted or substituted with -L1-Ar1.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 20 carbon atoms; Or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or combined with each other to form an aromatic hydrocarbon ring unsubstituted or substituted with -L1-Ar1.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 10 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms, or combine with each other to form an aromatic hydrocarbon ring unsubstituted or substituted with -L1-Ar1.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as or different from each other, and each independently a methyl group; or a phenyl group, or combine with each other to form a fluorene ring unsubstituted or substituted with -L1-Ar1.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are the same as or different from each other, and each independently a methyl group; or a phenyl group.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are methyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are phenyl groups.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are combined with each other to form a fluorene ring unsubstituted or substituted with -L1-Ar1.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formula 1-1,

G1 and G2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 30 carbon atoms; Or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms,

Any one of R3 to R10 is -L1-Ar1, the rest is hydrogen,

L1 and Ar1 are the same as defined in Formula 1 above,

In Formula 1-2 to 1-4,

any one of R3 to R10 and R101 to R108 is -L1-Ar1, the rest is hydrogen,

L1 and Ar1 are the same as defined in Formula 1 above.

According to an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently and independently a linear or branched alkyl group having 1 to 20 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently and independently a linear or branched alkyl group having 1 to 10 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, each independently and independently a methyl group; or a phenyl group.

According to an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and are each independently a linear or branched alkyl group having 1 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and are each independently a linear or branched alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and are each independently a linear or branched alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, G1 and G2 are methyl groups.

According to an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently represent a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently represent a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently represent a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, G1 and G2 are a phenyl group.

According to an exemplary embodiment of the present specification, L1 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; phenylene group; biphenylrylene group; or a naphthylene group.

According to an exemplary embodiment of the present specification, L1 is a direct bond.

According to an exemplary embodiment of the present specification, L1 is a phenylene group.

According to an exemplary embodiment of the present specification, L1 is a biphenylrylene group.

According to an exemplary embodiment of the present specification, L1 is a naphthylene group.

According to an exemplary embodiment of the present specification, Ar1 is a group represented by any one of the following structures.

In the structure,

* is a site bonded to L1 of Formula 1,

Y1 is a group represented by Formula 3,

Y2 to Y8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

y3 is an integer of 1 to 4, and when y3 is 2 or more, 2 or more Y3 are the same as or different from each other,

y4 is 1 or 2, and when y4 is 2, two Y4 are the same as or different from each other,

y5 is an integer of 1 to 4, and when y5 is 2 or more, 2 or more Y5 are the same as or different from each other,

y6 is an integer of 1 to 4, and when y6 is 2 or more, 2 or more Y6 are the same as or different from each other,

y7 is 1 or 2, and when y7 is 2, two Y7 are the same as or different from each other,

y8 is 1 or 2, and when y8 is 2, two Y8s are the same as or different from each other.

According to an exemplary embodiment of the present specification, Y2 is a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, Y2 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Y2 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Y2 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, Y2 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Y2 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Y2 is a monocyclic or polycyclic aryl group having 6 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, Y2 is a phenyl group; biphenyl group; or a naphthyl group.

According to an exemplary embodiment of the present specification, Y3 is hydrogen.

According to an exemplary embodiment of the present specification, Y4 is hydrogen.

According to an exemplary embodiment of the present specification, Y5 is hydrogen.

According to an exemplary embodiment of the present specification, Y6 is hydrogen.

According to an exemplary embodiment of the present specification, Y7 is hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, Y7 is hydrogen; a substituted or unsubstituted C1-C30 linear or branched alkyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Y7 is hydrogen; A substituted or unsubstituted C1-C20 linear or branched alkyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Y7 is hydrogen; a substituted or unsubstituted C1-C10 linear or branched alkyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, Y7 is hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Y7 is hydrogen; a linear or branched alkyl group having 1 to 20 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Y7 is hydrogen; a linear or branched alkyl group having 1 to 10 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, Y7 is hydrogen; methyl group; or a phenyl group.

According to an exemplary embodiment of the present specification, Y8 is hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, Y8 is hydrogen; a substituted or unsubstituted C1-C30 linear or branched alkyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Y8 is hydrogen; A substituted or unsubstituted C1-C20 linear or branched alkyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Y8 is hydrogen; a substituted or unsubstituted C1-C10 linear or branched alkyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, Y8 is hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Y8 is hydrogen; a linear or branched alkyl group having 1 to 20 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Y8 is hydrogen; a linear or branched alkyl group having 1 to 10 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, Y8 is hydrogen; methyl group; or a phenyl group.

According to an exemplary embodiment of the present specification, Ar1 is a group represented by any one of the following structures.

In the structure,

* is a site bonded to L1 of Formula 1,

Y1 is a group represented by the above formula (3).

According to an exemplary embodiment of the present specification, Chemical Formula 3 is a group represented by any one of the following structures.

In the structure,

The definition of L2 is the same as defined in Formula 3 above,

At least one of Ra1 to Ra4 is a substituted or unsubstituted alkyl group, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group,

At least one of Rb1 to Rb3 is a substituted or unsubstituted alkyl group, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group,

At least one of Rc1 and Rc2 is a substituted or unsubstituted alkyl group, and the remainder is hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group,

Rd1 is a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present specification, L2 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L2 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L2 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, L2 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L2 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L2 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, L2 is a direct bond; biphenylrylene group; or a phenylene group.

According to an exemplary embodiment of the present specification, L2 is a direct bond.

According to an exemplary embodiment of the present specification, L2 is a phenylene group.

According to an exemplary embodiment of the present specification, L2 is a biphenylrylene group.

According to an exemplary embodiment of the present specification, at least one of Ra1 to Ra4 is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of Ra1 to Ra4 is a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of Ra1 to Ra4 is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 10 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of Ra1 to Ra4 is a linear or branched alkyl group having 1 to 30 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of Ra1 to Ra4 is a linear or branched alkyl group having 1 to 20 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of Ra1 to Ra4 is a linear or branched alkyl group having 1 to 10 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of Ra1 to Ra4 is a methyl group; isopropyl group; or a tert-butyl group, the rest being the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a phenyl group.

According to an exemplary embodiment of the present specification, at least one of Rb1 to Rb3 is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of Rb1 to Rb3 is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of Rb1 to Rb3 is a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of Rb1 to Rb3 is a linear or branched alkyl group having 1 to 30 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of Rb1 to Rb3 is a linear or branched alkyl group having 1 to 20 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of Rb1 to Rb3 is a linear or branched alkyl group having 1 to 10 carbon atoms, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of Rb1 to Rb3 is a methyl group; isopropyl group; or a tert-butyl group, the rest being the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a phenyl group.

According to an exemplary embodiment of the present specification, at least one of Rc1 and Rc2 is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, and the remainder is hydrogen; heavy hydrogen; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of Rc1 and Rc2 is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, and the remainder is hydrogen; heavy hydrogen; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of Rc1 and Rc2 is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 10 carbon atoms, and the remainder is hydrogen; heavy hydrogen; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of Rc1 and Rc2 is a linear or branched alkyl group having 1 to 30 carbon atoms, and the remainder is hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of Rc1 and Rc2 is a linear or branched alkyl group having 1 to 20 carbon atoms, and the remainder is hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of Rc1 and Rc2 is a linear or branched alkyl group having 1 to 10 carbon atoms, and the remainder is hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of Rc1 and Rc2 is a methyl group; isopropyl group; or a tert-butyl group, the remainder being hydrogen; heavy hydrogen; or a phenyl group.

According to an exemplary embodiment of the present specification, Rd1 is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Rd1 is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Rd1 is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, Rd1 is a linear or branched alkyl group having 1 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Rd1 is a linear or branched alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Rd1 is a linear or branched alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, Rd1 is a methyl group; isopropyl group; or a tert-butyl group.

According to an exemplary embodiment of the present specification, Formula 1 is selected from the following compounds.

The present specification provides an organic light emitting device including the compound represented by Formula 1 above.

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

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

In the present specification, the 'layer' means compatible with the 'film' mainly used in the present technical field, and refers to a coating covering a desired area. The size of the 'layers' is not limited, and each 'layer' may have the same size or different sizes. According to an exemplary embodiment, the size of the 'layer' may be the same as the entire device, may correspond to the size of a specific functional area, and may be as small as a single sub-pixel.

In the present specification, the meaning that a specific material A is included in layer B means that i) one or more types of material A are included in one layer B, and ii) layer B is composed of one or more layers, and material A is multi-layered B. It includes everything included in one or more floors among the floors.

In the present specification, the meaning that a specific material A is included in the C layer or the D layer means i) is included in one or more of the one or more layers C, ii) is included in one or more of the one or more layers of the D layer, or iii ) means all of which are included in one or more C-layers and one or more D-layers, respectively.

The present specification includes a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above. do.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

According to an exemplary embodiment of the present specification, the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound.

According to an exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound.

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer.

According to an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer.

According to an exemplary embodiment of the present specification, the organic material layer includes an electron blocking layer.

According to an exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer.

According to an exemplary embodiment of the present specification, the organic light emitting device includes a hole injection layer, a hole transport layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer and an electron blocking layer. It further comprises one or more floors selected from.

According to an exemplary embodiment of the present specification, the organic light emitting device includes a first electrode; a second electrode provided to face the first electrode; a light emitting layer provided between the first electrode and the second electrode; and two or more organic material layers provided between the light emitting layer and the first electrode or between the light emitting layer and the second electrode.

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

According to an exemplary embodiment of the present specification, two or more hole transport layers are included between the light emitting layer and the first electrode. The two or more hole transport layers may include the same or different materials.

According to an exemplary embodiment of the present specification, the first electrode is an anode or a cathode.

According to an exemplary embodiment of the present specification, the second electrode is a negative electrode or an anode.

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

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

For example, the structure of the organic light emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 to 3 . 1 to 3 illustrate an organic light emitting device, but is not limited thereto.

1 illustrates a structure of an organic light emitting device in which a first electrode 102 , an organic material layer 111 , and a second electrode 110 are sequentially stacked on a substrate 101 . The compound represented by Formula 1 is included in the organic layer.

2 shows a first electrode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, an electron transport layer ( 108 ), the electron injection layer 109 , and the second electrode 110 are sequentially stacked. The structure of the organic light emitting device is exemplified. According to an exemplary embodiment of the present specification, the compound represented by Formula 1 is included in the electron injection layer, the electron transport layer, or the hole blocking layer.

3 shows a first electrode 102, a hole injection layer 103, a first hole transport layer 104-1, a second hole transport layer 104-2, a light emitting layer 106, an electron injection and The structure of the organic light emitting device in which the transport layer 112 and the second electrode 110 are sequentially stacked is exemplified. The compound represented by Formula 1 is included in the electron injection and transport layer.

The organic light emitting device of the present specification includes materials known in the art, except that the electron injection layer, the electron transport layer, the electron injection and transport layer, or the hole blocking layer includes the compound, that is, the compound represented by Formula 1 above. method can be prepared.

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode. It can be prepared by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. 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.

In addition, the compound represented by Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate. However, the manufacturing method is not limited thereto.

As the anode material, a material having a large work function is generally preferable to facilitate hole injection into the organic material layer. For example, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO ₂ : a combination of a metal such as Sb and an oxide; 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 material is preferably a material having a small work function to facilitate electron injection into the organic material layer. metals or alloys thereof such as, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; A multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The emission layer may include a host material and a dopant material. The host material 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, and the like, and heterocyclic-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but is not limited thereto.

Examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, periplanthene, and the like, having an arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and one or two or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group A substituent is substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but is not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

The hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injecting material has the ability to transport holes and thus has a hole receiving effect from the anode and an excellent hole injecting effect for the light emitting layer or the light emitting material. In addition, a material having an excellent ability to prevent migration of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferred. In addition, a material excellent in the ability to form a thin film is preferable. In addition, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material; hexanitrile hexaazatriphenylene-based organic substances; quinacridone-based organic substances; perylene-based organic materials; There are polythiophene-based conductive polymers such as anthraquinone and polyaniline, but is not limited thereto.

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

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. When the organic light emitting device according to an exemplary embodiment of the present specification includes an additional electron transport layer other than the electron transport layer comprising Formula 1, the electron transport material is a material capable of well injecting electrons from the cathode and transferring them to the light emitting layer As such, a material having high electron mobility is preferable. Specific examples include an Al complex of 8-hydroxyquinoline; complexes containing Alq _{3 ;} organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material, as used in accordance with the prior art. In particular, suitable cathode materials are conventional materials having a low work function, followed by a layer of aluminum or silver. Specifically, there are cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer is followed.

The electron injection layer is a layer that receives electrons from the electrode. When the organic light emitting device according to an exemplary embodiment of the present specification includes an additional electron injection layer other than the electron injection layer comprising Formula 1, the electron injection material has excellent ability to transport electrons, and the second electrode It is preferable to have an electron receiving effect from, and an excellent electron injection effect for the light emitting layer or the light emitting material. In addition, a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. derivatives thereof; metal complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

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

The electron blocking layer is a layer capable of improving the lifetime and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the emission layer. A known material can be used without limitation, and may be formed between the light emitting layer and the hole injection layer, or between the light emitting layer and a layer that simultaneously injects and transports holes.

The hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be formed under the same conditions as the electron injection layer in general. When the organic light emitting device according to an exemplary embodiment of the present specification includes an additional hole blocking layer other than the hole blocking layer comprising Formula 1, specifically, an oxadiazole derivative or a triazole derivative, a phenanthroline derivative, an aluminum complex, and the like, but is not limited thereto.

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

Hereinafter, in order to describe the present specification in detail, it will be described in detail with reference to Examples and Comparative Examples. However, the Examples and Comparative Examples according to the present specification may be modified in various other forms, and the scope of the present specification is not to be construed as being limited to the Examples and Comparative Examples described below. Examples and comparative examples of the present specification are provided to more completely explain the present specification to those of ordinary skill in the art.

Preparation Example 1-1: Preparation of compound E1

In a nitrogen atmosphere, E1-A (20 g, 53.2 mmol) and E1-B (19.8 g, 53.2 mmol) were placed in 400 ml of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (22 g, 159.5 mmol) was dissolved in 22 ml of water and thoroughly stirred, and then tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After reaction for 1 hour, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again put in 711 mL of chloroform 20 times to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound E1 (22 g, 62%, MS: [M+H] + = 669).

Preparation 1-2: Preparation of compound E2

Compound E2 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 768

Preparation Example 1-3: Preparation of compound E3

Compound E3 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 708

Preparation Example 1-4: Preparation of compound E4

Compound E4 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 608

Preparation Example 1-5: Preparation of compound E5

Compound E5 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 504

Preparation Example 1-6: Preparation of compound E6

Compound E6 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 669

Preparation Example 1-7: Preparation of compound E7

Compound E7 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 731

Preparation Example 1-8: Preparation of compound E8

Compound E8 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 685

Preparation Example 1-9: Preparation of compound E9

Compound E9 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 685

Preparation Example 1-10: Preparation of compound E10

Compound E10 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 745

Preparation Example 1-11: Preparation of compound E11

Compound E11 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 530

Preparation Example 1-12: Preparation of compound E12

Compound E12 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 609

Preparation 1-13: Preparation of compound E13

Compound E13 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 646

Preparation Example 1-14: Preparation of compound E14

Compound E14 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 580

Preparation Example 1-15: Preparation of compound E15

Compound E15 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 580

[Experimental Example 1]

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1000 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. In this case, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the thus prepared ITO transparent electrode, the following HI-A compound was thermally vacuum deposited to a thickness of 600 Å to form a hole injection layer. A first hole transport layer and a second hole transport layer were formed by sequentially vacuum-depositing 50 Å of the HAT compound and 60 Å of the HT-A compound on the hole injection layer.

Subsequently, the following BH compound and BD compound were vacuum-deposited at a weight ratio of 25:1 to a thickness of 20 nm on the second hole transport layer to form a light emitting layer.

On the emission layer, the compound E1 prepared in Preparation Example 1-1 and the following LiQ compound were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer to a thickness of 350 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 Å and aluminum to a thickness of 1000 Å on the electron injection and transport layer.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å/sec, the deposition rate of lithium fluoride of the negative electrode was maintained at 0.3 Å/sec, and the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was 1×10 ^{- By maintaining 7} to 5 × 10 ^-5 torr, an organic light emitting device was manufactured.

Experimental Examples 2 to 15

An organic light emitting diode was manufactured in the same manner as in Experimental Example 1, except that Compounds E2 to E15 of Preparation Examples shown in Table 1 were used instead of Compound E1 of Experimental Example 1, respectively.

Comparative Examples 1 to 15

An organic light emitting diode was manufactured in the same manner as in Experimental Example 1, except that compounds ET-A to ET-O in Table 1 below were used instead of Compound E1 of Experimental Example 1, respectively.

For the organic light emitting devices prepared in Experimental Examples 1 to 15 and Comparative Examples 1 to 15, the driving voltage and luminous efficiency were measured at a current density of ^{10 mA/cm 2} , and 90% of the initial luminance at a current density of ^{20 mA/cm 2} The time to become (T90) was measured. The results are shown in Table 1 below.

division compound Voltage
(V@10 mA/cm ² ) efficiency
(cd/A@10 mA/cm ² ) color coordinates
(x, y) Life (h)
T90 at 20 mA/cm ² ) Experimental Example 1 E1 4.38 4.69 (0.142, 0.096) 161 Experimental Example 2 E2 4.20 4.62 (0.142, 0.096) 155 Experimental Example 3 E3 4.25 4.64 (0.142, 0.096) 138 Experimental Example 4 E4 4.29 4.75 (0.142, 0.097) 134 Experimental Example 5 E5 4.47 4.51 (0.142, 0.096) 164 Experimental Example 6 E6 4.29 4.83 (0.142, 0.097) 142 Experimental Example 7 E7 4.34 4.58 (0.143, 0.096) 150 Experimental Example 8 E8 4.42 4.64 (0.142, 0.096) 184 Experimental Example 9 E9 4.30 4.84 (0.143, 0.096) 138 Experimental Example 10 E10 4.34 4.78 (0.142, 0.096) 158 Experimental Example 11 E11 4.34 4.51 (0.143, 0.097) 149 Experimental Example 12 E12 4.41 4.59 (0.142, 0.097) 193 Experimental Example 13 E13 4.29 4.60 (0.142, 0.096) 139 Experimental Example 14 E14 4.30 4.50 (0.142, 0.097) 127 Experimental Example 15 E15 4.51 4.62 (0.142, 0.096) 133 Comparative Example 1 ET-A 4.40 4.42 (0.142, 0.097) 78 Comparative Example 2 ET-B 4.22 4.36 (0.143, 0.096) 75 Comparative Example 3 ET-C 4.27 4.38 (0.142, 0.096) 67 Comparative Example 4 ET-D 4.31 4.48 (0.143, 0.096) 65 Comparative Example 5 ET-E 4.49 3.47 (0.142, 0.096) 117 Comparative Example 6 ET-F 4.31 3.69 (0.143, 0.097) 96 Comparative Example 7 ET-G 4.35 4.32 (0.142, 0.097) 73 Comparative Example 8 ET-H 4.44 3.31 (0.142, 0.096) 123 Comparative Example 9 ET-I 4.31 4.56 (0.142, 0.097) 67 Comparative Example 10 ET-J 4.35 4.51 (0.142, 0.096) 77 Comparative Example 11 ET-K 4.35 4.25 (0.142, 0.097) 72 Comparative Example 12 ET-L 4.42 4.33 (0.143, 0.096) 94 Comparative Example 13 ET-M 4.31 4.33 (0.142, 0.096) 68 Comparative Example 14 ET-N 4.32 4.25 (0.143, 0.096) 62 Comparative Example 15 ET-O 4.53 4.36 (0.142, 0.096) 64

As shown in Table 1, the compound represented by Chemical Formula 1 according to the present specification may be used in an organic material layer capable of simultaneously performing electron injection and electron transport of the organic light emitting device. Experimental Examples 1 to 15 of Table 1 and Comparing Comparative Examples 1, 3, 4, 7, and 9 to 15, the organic light emitting device including Formula 1 according to the present specification is significantly superior to the organic light emitting device including the compound not including Y1 in terms of lifespan. characteristics could be confirmed.

Comparing Experimental Examples 1 to 15 of Table 1 and Comparative Examples 2, 5, 6 and 8, the organic light emitting device including the compound of Formula 1 according to the present specification includes a compound in which Y1 is unsubstituted pyridine It was confirmed that the organic light emitting device showed significantly superior characteristics in terms of efficiency.

101: substrate
102: first electrode
103: hole injection layer
104: hole transport layer
105: electron blocking layer
106: light emitting layer
107: hole blocking layer
108: electron transport layer
109: electron injection layer
110: second electrode
111: organic layer
112: electron injection and transport layer
104-1: first hole transport layer
104-2: second hole transport layer

Claims (9)

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

In Formula 1,
A1 is a direct bond; O; or S;
R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may combine with each other to form a ring substituted or unsubstituted with -L1-Ar1,
R3 to R10 are the same as or different from each other, and each independently hydrogen; or -L1-Ar1;
When R1 and R2 are combined with each other to form a ring substituted with -L1-Ar1, R3 to R10 are hydrogen;
wherein R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or when combined with each other to form an unsubstituted ring, any one of R3 to R10 is -L1-Ar1, the rest is hydrogen;
L1 is a direct bond; Or a substituted or unsubstituted arylene group,
Ar1 is a group represented by any one of the following formulas 2-1 to 2-7,
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

[Formula 2-7]

In Formulas 2-1 to 2-7,
* is a site bonded to L1 of Formula 1,
Y1 is a group represented by the following formula (3),
At least one of X1 to X3 is N, the rest is CH,
At least one of X4 and X5 is N, the other is CH,
At least one of X6 and X7 is N, the other is CH,
X8 is N, Z1 is N or C, or X8 is CH, Z1 is N,
X9 is N, Z2 is N or C, or X9 is CH, Z2 is N,
X10 is N, Z3 is N or C, or X10 is CH, Z3 is N,
X11 is N, Z4 is N or C, or X11 is CH, Z4 is N,
Y2 to Y8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
y3 is an integer of 1 to 4, and when y3 is 2 or more, 2 or more Y3 are the same as or different from each other,
y4 is 1 or 2, and when y4 is 2, two Y4 are the same as or different from each other,
y5 is an integer of 1 to 4, and when y5 is 2 or more, 2 or more Y5 are the same as or different from each other,
y6 is an integer of 1 to 4, and when y6 is 2 or more, 2 or more Y6 are the same as or different from each other,
y7 is 1 or 2, and when y7 is 2, two Y7 are the same as or different from each other,
y8 is 1 or 2, and when y8 is 2, two Y8s are the same as or different from each other,
[Formula 3]

In Formula 3,

is a site bound to any one of Formulas 2-1 to 2-5,
L2 is a direct bond; Or a substituted or unsubstituted arylene group,
one to four of Q1 to Q5 are N, the others are CR,
At least one of R is a substituted or unsubstituted alkyl group, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted aryl group. The method according to claim 1, wherein R1 and R2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 30 carbon atoms; Or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a compound that combines with each other to form an aromatic hydrocarbon ring substituted or unsubstituted with -L1-Ar1. The method according to claim 1, wherein Formula 1 is a compound represented by any one of the following Formulas 1-1 to 1-4:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formula 1-1,
G1 and G2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 30 carbon atoms; Or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms,
Any one of R3 to R10 is -L1-Ar1, the rest is hydrogen,
L1 and Ar1 are the same as defined in Formula 1 above,
In Formula 1-2 to 1-4,
any one of R3 to R10 and R101 to R108 is -L1-Ar1, the rest is hydrogen,
L1 and Ar1 are the same as defined in Formula 1 above. The compound according to claim 1, wherein Ar1 is a group represented by any one of the following structures:

In the structure,
* is a site bonded to L1 of Formula 1,
Y1 is a group represented by Formula 3,
Y2 to Y8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
y3 is an integer of 1 to 4, and when y3 is 2 or more, 2 or more Y3 are the same as or different from each other,
y4 is 1 or 2, and when y4 is 2, two Y4 are the same as or different from each other,
y5 is an integer of 1 to 4, and when y5 is 2 or more, 2 or more Y5 are the same as or different from each other,
y6 is an integer of 1 to 4, and when y6 is 2 or more, 2 or more Y6 are the same as or different from each other,
y7 is 1 or 2, and when y7 is 2, two Y7 are the same as or different from each other,
y8 is 1 or 2, and when y8 is 2, two Y8s are the same as or different from each other. The compound according to claim 1, wherein Formula 3 is a group represented by any one of the following structures:

In the structure,
The definition of L2 is the same as defined in Formula 3 above,
At least one of Ra1 to Ra4 is a substituted or unsubstituted alkyl group, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group,
At least one of Rb1 to Rb3 is a substituted or unsubstituted alkyl group, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group,
At least one of Rc1 and Rc2 is a substituted or unsubstituted alkyl group, and the remainder is hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group,
Rd1 is a substituted or unsubstituted alkyl group. The compound according to claim 1, wherein Formula 1 is selected from the following compounds:

a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the compound of any one of claims 1 to 6. The organic light-emitting device of claim 7 , wherein the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound. The organic light-emitting device of claim 7 , wherein the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound.

Images