KR102405393B1 - Organic light emitting device - Google Patents

Abstract

The present specification provides an organic light emitting device including a first organic material layer including the compound of Formula 1 and a second organic layer including the compound of Formula 2.

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

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

This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0100245 filed with the Korean Intellectual Property Office on August 16, 2019, the entire contents of which are incorporated herein by reference.

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

Chinese Patent Publication No. 108137618

An organic light emitting device is described herein.

An exemplary embodiment of the present specification is a positive electrode; cathode; and an organic material layer provided between the anode and the cathode, wherein the organic material layer comprises a first organic material layer including a compound represented by the following formula (1) and a second organic material layer including a compound represented by the following formula (2) It provides an organic light emitting device comprising.

[Formula 1]

In Formula 1,

Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group,

At least one of Ar1 and Ar2 contains deuterium,

Ar3 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L1 to L3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; halogen group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r1 is an integer of 0 to 4, and when r1 is 2 or more, R1 of 2 or more are the same as or different from each other,

r2 is an integer of 0 to 3, and when r2 is 2 or more, 2 or more R2 are the same as or different from each other,

[Formula 2]

In Formula 2,

Y is O; or S;

1 to 4 of G1 to G16 are connected to Formula 3 below,

The remainder not connected to Formula 3 among G1 to G16 is hydrogen; or deuterium, or adjacent substituents combine with each other to form a substituted or unsubstituted benzene ring,

[Formula 3]

In Formula 3,

X1 is N or C(R31), X2 is N or C(R32), X3 is N or C(R33), and at least one of X1 to X3 is N,

Ar21 and Ar22 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with adjacent R31, R32 or R33 to form a substituted or unsubstituted ring,

R31, R32 and R33 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with adjacent Ar21 or Ar22;

L4 is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

는 상기 화학식 2에 연결되는 위치이다.

is a position connected to Formula 2 above.

The organic light emitting device described herein includes the compound represented by Formula 1 in the first organic layer, and the compound represented by Formula 2 in the second organic layer, thereby having a low driving voltage, excellent efficiency characteristics, and excellent lifespan. have

1, 2 and 8 show examples of an organic light emitting device according to an exemplary embodiment of the present specification.
3 to 7 show examples of organic light emitting devices including two or more stacks.

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

The present specification provides an organic light emitting device including a first organic material layer including a compound represented by Formula 1 and a second organic material layer including a compound represented by Formula 2 at the same time.

In Chemical Formula 1, an aryl group or a heterocyclic group is connected to the 2nd, 9th and 10th carbons of anthracene. In addition, since Formula 1 contains one or more deuterium, the efficiency and lifespan of the device are improved. Specifically, when hydrogen is replaced with deuterium, the chemical properties of the compound hardly change. However, since the atomic weight of deuterium is twice that of hydrogen, deuterated compounds may change their physical properties. For example, a compound substituted with deuterium has a lower vibrational energy level. C-D bonds may also improve the stability of the compound. Accordingly, the compound represented by Formula 1 may improve the lifespan of the device by including deuterium.

The compound of Formula 1 containing deuterium may be prepared by a known deuterium reaction. According to an exemplary embodiment of the present specification, the compound represented by Chemical Formula 1 is formed by using a deuterated compound as a precursor, or deuterium through a deuterium exchange reaction using an acid catalyst or a metal catalyst using a deuterated solvent. It can also be incorporated into a compound.

Formula 2 is a structure in which an N-containing heterocyclic group is connected to a polycyclic heterocyclic group including O or S. The polycyclic heterocyclic group containing O or S is specifically a spiro structure in which fluorene and xanthene, or fluorene and thioxanthene are fused. The spiro structure has a steric hindrance in that fluorene and (thio)xanthene are positioned on a plane perpendicular to each other in 3D space, respectively. The steric hindrance prevents crystallization during film formation and increases thermal stability so that a layer can be stably formed even at a high deposition temperature. Therefore, the compound of Formula 2 has a high glass transition temperature and excellent thermal stability, and shows stable blue emission in the solid state.

When the compound of Formula 1 is used as a host of the light emitting layer (EML) and the compound of Formula 2 is used in the electron transport layer (ETL), the energy relationship between the light emitting layer and the electron transport layer is as follows.

G _ETL - G _EML > 0.0 eV

(G _EML refers to S0-S1/S0 Gap in the light emitting layer (EML), and G _ETL refers to S0-S1/S0 Gap in the electron transport layer (ETL).)

Due to the above energy relationship, the organic light emitting device including the compound of Formula 1 and the compound of Formula 2 has excellent hole blocking effect from the light emitting layer to the electron transport layer, and thus has excellent high efficiency and long lifespan.

In addition, the relationship between the electron affinity (electron affinity (eV)) of the organic light emitting device using the compound of Formula 1 as a host for the light emitting layer (EML) and the compound of Formula 2 for the electron transport layer (ETL) is as follows .

E _ETL - E _EML > 0.2 eV

Due to the electron affinity relationship, the organic light emitting device including the compound of Formula 1 and the compound of Formula 2 may induce proper electron transport from the electron transport layer to the emission layer.

In addition, the long-life and high-efficiency characteristics of Chemical Formula 1, the long-life characteristics of Chemical Formula 2, and thermal stability due to the high glass transition temperature are secured, so that an organic light emitting diode with improved stability can be obtained.

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

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

In the present specification, the "layer" is a meaning compatible with the "film" mainly used in the art, and means 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. In one embodiment, the size of a “layer” may be equal to the size of 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 layers C and one or more layers D, respectively.

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

In the present specification, the degree of deuteration can be confirmed by a known method such as nuclear magnetic resonance spectroscopy ( ¹ H NMR) or GC/MS.

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

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

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

은 연결되는 부위를 의미한다.In this specification,

denotes a part to be connected.

또는

의 치환기가 될 수 있다. In the present specification, that two or more substituents are connected means that hydrogen of any one substituent is connected with another substituent. For example, an isopropyl group and a phenyl group are linked

or

It can be a substituent of

또는

의 치환기가 될 수 있다. 4 이상의 치환기가 연결되는 것에도 전술한 것과 동일하게 적용된다.In the present specification, three substituents are connected to (substituent 1)-(substituent 2)-(substituent 3) as well as consecutively connected (substituent 1) to (substituent 2) and (substituent 3) It also includes connecting. For example, two phenyl groups and an isopropyl group are linked

or

It can be a substituent of The same applies to those in which 4 or more substituents are connected.

In the present specification, "substituted with A or B" includes not only the case substituted with A or only B, but also the case where both A and B are substituted.

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 alkyl group includes a straight or branched chain, and the number of carbon atoms is not particularly limited, but is 1 to 60, 1 to 30, or 1 to 20. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and the like, and the alkyl group may be a straight chain or a branched chain. The group includes an n-propyl group and an isopropyl group, and the butyl group includes an n-butyl group, an isobutyl group and a tert-butyl group.

In the present specification, the number of carbon atoms of the cycloalkyl group is not particularly limited, but is 3 to 60, 3 to 30, or 3 to 20. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but is not limited thereto.

In the present specification, the description of the above-described alkyl group may be applied to the alkyl group of the alkoxy group.

In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group, and the number of carbon atoms is not particularly limited, but is 6 to 60, 6 to 30, or 6 to 20. The monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and the like, 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, fluoranthenyl group, triphenylenyl group, etc. , but is not limited thereto.

In the present specification, the 9th carbon atom (C) of the fluorenyl group may be substituted with an alkyl group, an aryl group, or the like, and two substituents may be bonded to each other to form a spiro structure such as cyclopentane or fluorene.

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

In the present specification, the silyl group may be represented by the formula of -SiY _a Y _b Y _c , wherein Y _a , Y _b and Y _c are each hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group is specifically trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, dimethylphenylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. but is not limited thereto.

In the present specification, the boron group may be represented by the formula of -BY _d Y _e , wherein Y _d and Y _e are each hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes, but is not limited to, a dimethyl boron group, a diethyl boron group, a tert-butylmethyl boron group, a vinyl methyl boron group, a propylmethyl boron group, a methylphenyl boron group, a diphenyl boron group, a phenyl boron group, and the like. .

In the present specification, the amine group may be represented by -NRaRb, wherein Ra and Rb are each hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heteroaryl group, but is not limited thereto. The amine group is selected from the group consisting of an alkylamine group, an alkylarylamine group, an arylamine group, a heteroarylamine group, an alkylheteroarylamine group, and an arylheteroarylamine group, depending on the type of the substituent (Ra, Rb) to be bonded. can be

In the present specification, the alkylamine group refers to an amine group substituted with an alkyl group, and the number of carbon atoms is not particularly limited, but may be 1 to 40 or 1 to 20. Specific examples of the alkylamine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, and a diethylamine group.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, and a substituted or unsubstituted diarylamine group. The aryl group in the arylamine group may be a monocyclic or polycyclic aryl group. Specific examples of the arylamine group include, but are not limited to, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a diphenylamine group, and a phenylnaphthylamine group.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, and a substituted or unsubstituted diheteroarylamine group.

In the present specification, the heterocyclic group is a ring group including at least one of N, O, S, and Si as a heteroatom, and the number of carbon atoms is not particularly limited, but is 2 to 60, or 2 to 30. Examples of the heterocyclic group include, but are not limited to, a pyridyl group; quinoline group; thiophene group; dibenzothiophene group; furan group; dibenzofuran group; naphthobenzofuran group; a carbazole group; benzocarbazole group; and a naphthobenzothiophene group, but is not limited thereto.

As used herein, "adjacent" The group may mean a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent positioned sterically close to the substituent, or another substituent substituted on the atom in which the substituent is substituted.

In the present specification, "a ring formed by bonding adjacent groups" is a hydrocarbon ring; or a heterocyclic ring.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and the description of the aryl group described above may be applied except that the aromatic hydrocarbon ring is not monovalent, and the aliphatic hydrocarbon ring is Except for the non-monovalent, the above description of the cycloalkyl group may be applied.

In the present specification, the description of the heterocyclic group may be applied except that the heterocycle is not monovalent.

As used herein, the aromatic hydrocarbon ring means a ring in which pi electrons are completely conjugated and planar.

In the present specification, the aliphatic hydrocarbon ring refers to all hydrocarbon rings except for the aromatic hydrocarbon ring. The substituted aliphatic hydrocarbon ring also includes an aliphatic hydrocarbon ring in which an aromatic ring is condensed.

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

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

Hereinafter, the substituent of Formula 1 will be described.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group, and at least one of Ar1 and Ar2 includes deuterium.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6-C20 aryl group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6-C10 aryl group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represent a monocyclic to tricyclic aryl group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represent a substituted or unsubstituted monocyclic or bicyclic aryl group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently 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 phenanthrenyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluoranthenyl group; a substituted or unsubstituted phenalene group; a substituted or unsubstituted pyrenyl group; a substituted or unsubstituted chrysenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted benzofluorenyl group; Or a substituted or unsubstituted spirobifluorenyl group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium; a biphenyl group unsubstituted or substituted with deuterium; or a naphthyl group unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, at least one of Ar1 and Ar2 is substituted with deuterium. That is, at least one of Ar1 and Ar2 is an aryl group substituted with deuterium.

In the exemplary embodiment of the present specification, Ar1 is substituted with deuterium. That is, Ar1 is an aryl group substituted with deuterium.

In an exemplary embodiment of the present specification, Ar2 is substituted with deuterium. That is, Ar2 is an aryl group substituted with deuterium.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are substituted with deuterium. That is, Ar1 and Ar2 are each an aryl group substituted with deuterium.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted C6-C20 aryl group.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted C6-C10 aryl group.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted monocyclic to tricyclic aryl group.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted monocyclic or bicyclic aryl group.

In an exemplary embodiment of the present specification, Ar3 is 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 phenanthrenyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluoranthenyl group; a substituted or unsubstituted phenalene group; a substituted or unsubstituted pyrenyl group; a substituted or unsubstituted chrysenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted benzofluorenyl group; Or a substituted or unsubstituted spirobifluorenyl group.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

In an exemplary embodiment of the present specification, Ar3 is a phenyl group unsubstituted or substituted with deuterium; a biphenyl group unsubstituted or substituted with deuterium; or a naphthyl group unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted C 2 to C 30 heteroarylene group.

In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted C 2 to C 20 heteroarylene group.

In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted fluorenylene group; a substituted or unsubstituted benzofluorenylene group; a substituted or unsubstituted divalent pyridine group; a substituted or unsubstituted divalent pyrimidine group; a substituted or unsubstituted divalent carbazole group; a substituted or unsubstituted divalent furan group; a substituted or unsubstituted divalent thiophene group; A substituted or unsubstituted divalent dibenzofuran group; a substituted or unsubstituted divalent dibenzothiophene group; A substituted or unsubstituted divalent naphthobenzofuran group; or a substituted or unsubstituted divalent naphthobenzothiophene group.

In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; or an arylene group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; a biphenylene group unsubstituted or substituted with deuterium; Or a naphthylene group unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; Or a naphthylene group unsubstituted or substituted with deuterium.

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

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

In one embodiment of the present specification, L1 is a direct bond; a phenylene group unsubstituted or substituted with deuterium; Or a naphthylene group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, L2 is a direct bond.

In one embodiment of the present specification, L3 is a direct bond; a phenylene group unsubstituted or substituted with deuterium; Or a naphthylene group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, L3 are the same as or different from each other, and each independently a direct bond; phenylene group; or a naphthylene group.

In one embodiment of the present specification, L3 is a direct bond.

In one embodiment of the present specification, L1 to L3 are a direct bond.

In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently is any one selected from a direct bond or the following structure.

The structure is deuterium; halogen group; nitrile group; an alkyl group; aryl group; and a substituent selected from the group consisting of a heteroaryl group or a substituent to which two or more substituents are connected, or does not have any substituents.

In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; or deuterium.

In an exemplary embodiment of the present specification, r1 is 0.

In one embodiment of the present specification, r2 is 0.

In an exemplary embodiment of the present specification, when the compound represented by Formula 1 is substituted with deuterium, 30% or more is substituted with deuterium. In another exemplary embodiment, the structure of Formula 1 is substituted by 40% or more with deuterium. In another exemplary embodiment, the structure of Formula 1 is substituted with deuterium by 60% or more. In another exemplary embodiment, 80% or more of the structure of Formula 1 is substituted with deuterium. In another exemplary embodiment, the structure of Formula 1 is 100% substituted with deuterium.

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

Hereinafter, the substituent of Formula 2 will be described.

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

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

In an exemplary embodiment of the present specification, one or two of G1 to G16 are connected to Formula 3 above.

In the exemplary embodiment of the present specification, one of G1 to G16 is connected to Formula 3 above.

In an exemplary embodiment of the present specification, G1 is connected to Formula 3 above.

In an exemplary embodiment of the present specification, G2 is connected to Formula 3 above.

In the exemplary embodiment of the present specification, G3 is connected to Formula 3 above.

In an exemplary embodiment of the present specification, G4 is connected to Formula 3 above.

In the exemplary embodiment of the present specification, G5 is connected to Formula 3 above.

In the exemplary embodiment of the present specification, G6 is connected to Formula 3 above.

In an exemplary embodiment of the present specification, G7 is connected to Formula 3 above.

In an exemplary embodiment of the present specification, G8 is connected to Formula 3 above.

In an exemplary embodiment of the present specification, G9 is connected to Formula 3 above.

In an exemplary embodiment of the present specification, G10 is connected to Formula 3 above.

In an exemplary embodiment of the present specification, G11 is connected to Formula 3 above.

In an exemplary embodiment of the present specification, G12 is connected to Formula 3 above.

In an exemplary embodiment of the present specification, G13 is connected to Formula 3 above.

In an exemplary embodiment of the present specification, G14 is connected to Formula 3 above.

In an exemplary embodiment of the present specification, G15 is connected to Formula 3 above.

In an exemplary embodiment of the present specification, G16 is connected to Formula 3 above.

In the exemplary embodiment of the present specification, the rest not connected to Formula 3 among G1 to G16 are the same as or different from each other, and each independently hydrogen; or deuterium, or adjacent substituents combine with each other to form a substituted or unsubstituted benzene ring.

In the exemplary embodiment of the present specification, the rest not connected to Formula 3 among G1 to G16 are the same as or different from each other, and each independently hydrogen; or deuterium.

In an exemplary embodiment of the present specification, G1 and G2 are combined with each other to form a substituted or unsubstituted benzene ring.

In an exemplary embodiment of the present specification, G15 and G16 are combined with each other to form a substituted or unsubstituted benzene ring.

In an exemplary embodiment of the present specification, X1 is N or C(R31).

In an exemplary embodiment of the present specification, X2 is N or C(R32).

In an exemplary embodiment of the present specification, X3 is N or C(R33).

In one embodiment of the present specification, at least one of X1 to X3 is N.

In one embodiment of the present specification, at least two of X1 to X3 are N.

In one embodiment of the present specification, X1 to X3 are all N.

In an exemplary embodiment of the present specification, X1 is N, X2 is N, and X3 is C(R33). In another exemplary embodiment, R33 is combined with Ar22 to form a benzene ring.

In the exemplary embodiment of the present specification, X1 is N, X2 is C(R32), and X3 is N. In another exemplary embodiment, R33 is combined with Ar22 to form a benzene ring.

In an exemplary embodiment of the present specification, Ar21 and Ar22 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, or combined with adjacent R31, R32 or R33 to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with R41; Or a heterocyclic group substituted or unsubstituted with R42, or combined with adjacent R31, R32 or R33 to form an aromatic hydrocarbon ring substituted or unsubstituted with R41.

In an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with R41; Or a heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with R42, or a C6-C30 aromatic hydrocarbon ring substituted or unsubstituted with R41 by combining with adjacent R31, R32 or R33.

In an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with R41; Or a C2-C20 heterocyclic group substituted or unsubstituted with R42, or a C6-C30 aromatic hydrocarbon ring substituted or unsubstituted with R41 by combining with adjacent R31, R32 or R33.

In the exemplary embodiment of the present specification, when one of Ar21 and Ar22 is an aryl group, the aryl group may include a phenyl group; biphenyl group; terphenyl group; naphthyl group; phenanthrenyl group; triphenylene group; fluoranthenyl group; phenalene group; anthracenyl group; fluorenyl group; Or a dimethyl fluorenyl group, the substituent is unsubstituted or substituted with R41.

In the exemplary embodiment of the present specification, when one of Ar21 and Ar22 is a heterocyclic group, the heterocyclic group is unsubstituted or substituted with R42, and a monocyclic to 5-ring heterocyclic group containing N, O, S or Si to be.

In an exemplary embodiment of the present specification, when one of Ar21 and Ar22 is a heterocyclic group, the heterocyclic group is a carbazole group; phenylcarbazole group; benzocarbazole group; an indenocarbazole group; dibenzothiophene group; dibenzofuran group; dibenzosilole group; phenoxazine; phenothiazine group; phenazine group; acridine group; dihydrophenazine group; dihydroacridine group; pyridyl group; pyrimidyl group; quinoline group; isoquinoline group; quinazoline group; pyridopyrimidine group; pyridopyrazine group; pyrimidoindol; Or a pyridoindole group, the substituent is unsubstituted or substituted with R42.

In an exemplary embodiment of the present specification, Ar21 and Ar22 are a phenyl group; biphenyl group; terphenyl group; naphthyl group; phenanthrenyl group; triphenylene group; fluoranthenyl group; phenalene group; anthracenyl group; fluorenyl group; dimethyl fluorenyl group; a carbazole group; phenylcarbazole group; benzocarbazole group; an indenocarbazole group; dibenzothiophene group; dibenzofuran group; dibenzosilole group; phenoxazine; phenothiazine group; phenazine group; acridine group; dihydrophenazine group; dihydroacridine group; pyridyl group; pyrimidyl group; quinoline group; isoquinoline group; quinazoline group; pyridopyrimidine group; pyridopyrazine group; pyrimidoindol; and a substituent selected from the group consisting of a pyridoindole group, or a substituent to which two or more groups selected from the group are connected, wherein the substituent is deuterium; nitrile group; methyl group; ethyl group; Profile group; isopropyl group; n-butyl group; tert-butyl group; trifluoromethyl group; methoxy group; ethoxy group; trimethylsilyl group; Or it may be substituted with a triphenylsilyl group.

In an exemplary embodiment of the present specification, Ar21 is combined with R31 to form a substituted or unsubstituted benzene ring.

In an exemplary embodiment of the present specification, Ar21 is combined with R32 to form a substituted or unsubstituted benzene ring.

In an exemplary embodiment of the present specification, Ar22 is combined with R32 to form a substituted or unsubstituted benzene ring.

In an exemplary embodiment of the present specification, Ar22 is combined with R33 to form a substituted or unsubstituted benzene ring.

In an exemplary embodiment of the present specification, R41 and R42 are the same as or different from each other, and each independently deuterium; halogen group; nitrile group; an alkyl group; haloalkyl group; alkoxy group; silyl group; aryl group; and one selected from the group consisting of a heterocyclic group, or a substituent to which two or more groups selected from the group are connected.

In an exemplary embodiment of the present specification, R41 and R42 are the same as or different from each other, and each independently deuterium; halogen group; nitrile group; an alkyl group having 1 to 10 carbon atoms; a haloalkyl group having 1 to 10 carbon atoms; an alkoxy group having 1 to 10 carbon atoms; an alkylsilyl group having 1 to 30 carbon atoms; an arylsilyl group having 6 to 50 carbon atoms; an aryl group having 6 to 30 carbon atoms; and one selected from the group consisting of a heterocyclic group having 2 to 30 carbon atoms, or a substituent to which two or more groups selected from the group are connected.

In an exemplary embodiment of the present specification, R41 and R42 are the same as or different from each other, and each independently deuterium; halogen group; nitrile group; an alkyl group having 1 to 6 carbon atoms; a haloalkyl group having 1 to 6 carbon atoms; an alkoxy group having 1 to 6 carbon atoms; an alkylsilyl group having 1 to 20 carbon atoms; an arylsilyl group having 6 to 30 carbon atoms; an aryl group having 6 to 20 carbon atoms; and one selected from the group consisting of a heterocyclic group having 2 to 20 carbon atoms, or a substituent to which two or more groups selected from the group are connected.

In an exemplary embodiment of the present specification, R41 and R42 are the same as or different from each other, and each independently deuterium; nitrile group; methyl group; ethyl group; Profile group; isopropyl group; n-butyl group; tert-butyl group; trifluoromethyl group; methoxy group; ethoxy group; trimethylsilyl group; triphenylsilyl group; phenyl group; biphenyl group; terphenyl group; naphthyl group; phenanthrenyl group; triphenylene group; fluoranthenyl group; phenalene group; anthracenyl group; fluorenyl group; dimethyl fluorenyl group; a carbazole group; phenylcarbazole group; benzocarbazole group; an indenocarbazole group; dibenzothiophene group; dibenzofuran group; dibenzosilole group; phenoxazine; phenothiazine group; phenazine group; acridine group; dihydrophenazine group; dihydroacridine group; pyridyl group; pyrimidyl group; quinoline group; isoquinoline group; quinazoline group; pyridopyrimidine group; pyridopyrazine group; pyrimidoindol; and one selected from the group consisting of pyridoindole, or a substituent to which two or more groups selected from the group are connected.

In an exemplary embodiment of the present specification, R31, R32 and R33 are the same as or different from each other, and each independently hydrogen; or deuterium, or combines with adjacent Ar21 or Ar22 to form a substituted or unsubstituted benzene ring.

In the exemplary embodiment of the present specification, Chemical Formula 3 is represented by any one of the following Chemical Formulas 301 to 303.

[Formula 301]

[Formula 302]

[Formula 303]

In Formulas 301 to 303,

The definition of L4 is as defined in Formula 3,

X1 to X3 are the same as or different from each other, each independently represent N or CH, and at least one of X1 to X3 is N,

Ar23 and Ar24 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R34 is hydrogen; heavy hydrogen; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r34 is an integer of 0 to 4, and when r34 is 2 or more, R34 is the same as or different from each other.

In the exemplary embodiment of the present specification, the definitions of Ar23 and A24 are the same as those of Ar21 and Ar22.

In an exemplary embodiment of the present specification, R34 is hydrogen or deuterium.

In one embodiment of the present specification, L4 is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group.

In one embodiment of the present specification, L4 is a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted C 2 to C 30 divalent heterocyclic group.

In one embodiment of the present specification, L4 is a direct bond; an arylene group having 6 to 30 carbon atoms; or a divalent heterocyclic group having 2 to 30 carbon atoms, and the arylene group or the divalent heterocyclic group is a nitrile group; an alkyl group having 1 to 10 carbon atoms; an aryl group having 6 to 30 carbon atoms; and one substituent selected from the group consisting of a heterocyclic group having 2 to 30 carbon atoms, or is unsubstituted or substituted with a divalent substituent to which two or more groups selected from the group are connected.

In one embodiment of the present specification, L4 is a direct bond; phenylene group; biphenylene group; terphenylene group; naphthylene group; anthracenylene group; a divalent phenanthrenyl group; a divalent triphenylene group; a divalent fluoranthenyl group; a divalent phenalene group; a divalent fluorenyl group; a divalent dimethyl fluorenyl group; a divalent carbazole group; a divalent phenylcarbazole group; a divalent benzocarbazole group; a divalent indenocarbazole group; a divalent dibenzothiophene group; a divalent dibenzofuran group; divalent dibenzocyrol group; divalent phenoxazine; a divalent phenothiazine group; divalent phenazine group; a divalent acridine group; divalent dihydrophenazine group; a divalent dihydroacridine group; a divalent pyridyl group; a divalent pyrimidyl group; a divalent quinoline group; a divalent isoquinoline group; a divalent quinazoline group; a divalent pyridopyrimidine group; a divalent pyridopyrazine group; bivalent pyrimidoindol; or a divalent pyridoindole group, wherein L4 is a nitrile group; an alkyl group having 1 to 10 carbon atoms; an aryl group having 6 to 30 carbon atoms; and one substituent selected from the group consisting of a heterocyclic group having 2 to 30 carbon atoms, or is unsubstituted or substituted with a divalent substituent to which two or more groups selected from the group are connected.

In one embodiment of the present specification, L4 is a direct bond; phenylene group; biphenylene group; or a naphthylene group.

In one embodiment of the present specification, L4 is a direct bond.

In an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with R41; Or a heterocyclic group substituted or unsubstituted with R42, or combined with adjacent R31, R32 or R33 to form an aromatic hydrocarbon ring substituted or unsubstituted with R41,

R41 and R42 are the same as or different from each other, and each independently represent deuterium; halogen group; nitrile group; an alkyl group having 1 to 6 carbon atoms; a haloalkyl group having 1 to 6 carbon atoms; an alkoxy group having 1 to 6 carbon atoms; an alkylsilyl group having 1 to 20 carbon atoms; an arylsilyl group having 6 to 30 carbon atoms; an aryl group having 6 to 20 carbon atoms; and one selected from the group consisting of a heterocyclic group having 2 to 20 carbon atoms, or a substituent to which two or more groups selected from the group are connected.

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

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

In Formulas 2-1 to 2-4,

The definitions of Y, L4, X1 to X3, Ar21 and Ar22 are as defined in Formula 2.

은 서로 동일하거나 상이하다.In one embodiment of the present specification, the formula 2-3

are the same or different from each other.

In an exemplary embodiment of the present specification, the compound represented by Formula 2 is any one selected from the following compounds.

The compound according to an exemplary embodiment of the present specification may be prepared by a method described below. If necessary, a substituent may be added or excluded, and the position of the substituent may be changed. In addition, based on techniques known in the art, starting materials, reactants, reaction conditions, etc. can be changed.

For example, the compounds represented by Formulas 1 and 2 may have a core structure as shown in Formulas 1 and 2 below. 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. A substituent may be combined as in the following general formulas 1 and 2, but is not limited thereto.

[General formula 1]

[General formula 2]

In Formula 1, Ar1 to Ar3, Ar21, Ar22, L1 to L4, Y, and X1 to X3 are the same as defined in Formulas 1 and 2, and Z11 to Z13 and Z2 are the same as or different from each other, and each independently to a halogen group (preferably chloro, bromo, iodo).

Hereinafter, an organic light emitting device will be described.

The organic light emitting device of the present specification is a conventional organic material layer, except that the first organic material layer is formed using the compound represented by Chemical Formula 1 and the second organic material layer is formed using the compound represented by Chemical Formula 2 described above. It can be manufactured according to the manufacturing method and material of the light emitting device.

The first organic layer including the compound represented by Formula 1 and the second organic layer including the compound represented by Formula 2 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

The organic material layer of the organic light emitting device of the present specification may have a structure including only the first organic material layer and the second organic material layer, or may have a structure further including an additional organic material layer. As the additional organic material layer, one of a hole injection layer, a hole transport layer, a layer that transports and injects holes at the same time, an electron suppression layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously transports and injects electrons, and a hole blocking layer It can be more than a layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number or a larger number of organic material layers.

In the organic light-emitting device according to the exemplary embodiment of the present specification, the first organic material layer is a light-emitting layer, and the second organic material layer is provided between the cathode and the light-emitting layer.

In the organic light emitting device according to an exemplary embodiment of the present specification, the first organic material layer is a light emitting layer.

In the organic light emitting device according to the exemplary embodiment of the present specification, the second organic material layer is a hole blocking layer, an electron transport layer, an electron injection layer, or a layer that simultaneously transports and injects electrons.

In the organic light emitting diode according to an exemplary embodiment of the present specification, the second organic material layer is a hole blocking layer, an electron transport layer, or an electron injection layer.

In the organic light emitting device according to an exemplary embodiment of the present specification, the second organic material layer is a hole blocking layer.

In the organic light emitting device according to an exemplary embodiment of the present specification, the second organic material layer is an electron transport layer.

In the organic light emitting diode according to an exemplary embodiment of the present specification, the second organic material layer is provided in contact with the first organic material layer.

In the organic light emitting device according to an exemplary embodiment of the present specification, the first organic material layer is a light emitting layer, and the compound represented by Formula 1 is included as a host.

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

In the organic light emitting device according to an exemplary embodiment of the present specification, the first organic material layer includes a fluorescent host.

In the organic light emitting device according to the exemplary embodiment of the present specification, the organic material layer includes two or more light emitting layers, and one of the two or more light emitting layers is the first organic material layer.

In the organic light emitting diode according to the exemplary embodiment of the present specification, the maximum emission peaks of the two or more emission layers are different from each other.

In the organic light emitting device according to the exemplary embodiment of the present specification, a first organic material layer of the two or more light emitting layers includes a fluorescent dopant, and the other light emitting layer includes a phosphorescent dopant.

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

In the organic light-emitting device according to an exemplary embodiment of the present specification, it includes two or more light-emitting layers, and the maximum emission peak of one light-emitting layer (light-emitting layer 1) is 400 nm to 500 nm, and the other light-emitting layer (light-emitting layer 2) The maximum emission peak of 510 nm to 580 nm; Alternatively, it may exhibit a maximum emission peak of 610 nm and 680 nm. In this case, the light emitting layer 1 is a first organic material layer.

The structure of the organic light emitting device of the present specification may have a structure as shown in FIGS. 1, 2 and 8 , but is not limited thereto.

1 shows a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a cathode 11 The structure of this sequentially stacked organic light emitting device is exemplified. In such a structure, the compound represented by Formula 1 may be included in the light emitting layer 6 , and the compound represented by Formula 2 may be included in the hole blocking layer 7 or the electron injection and transport layer 8 .

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, an electron injection and transport layer 8, and a cathode 11 The structure of this sequentially stacked organic light emitting device is exemplified. In such a structure, the compound represented by Formula 1 may be included in the emission layer 6 , and the compound represented by Formula 2 may be included in the electron injection and transport layer 8 .

8 shows a substrate 1, an anode 2, a p-doped hole transport layer 4p, a hole transport layer 4R, 4G, 4B, a light emitting layer 6RP, 6GP, 6BF, a first electron transport layer 9a, The structure of the organic light emitting device in which the second electron transport layer 9b, the electron injection layer 10, the cathode 11 and the capping layer 14 are sequentially stacked is illustrated. In such a structure, the compound represented by Formula 1 may be included in the light emitting layers 6RP, 6GP, and 6BF, and the compound represented by Formula 2 may include a first electron transport layer 9a and a second electron transport layer 9b. It may be included in one or more mezzanine floors.

According to an exemplary embodiment of the present specification, the organic light emitting device may have a tandem structure in which two or more independent devices are connected in series. In an exemplary embodiment, the tandem structure may have a form in which each organic light emitting device is bonded to a charge generating layer. Since a device having a tandem structure can be driven at a lower current than a unit device based on the same brightness, there is an advantage in that the lifespan characteristics of the device are greatly improved.

According to an exemplary embodiment of the present specification, the organic material layer may include: a first stack including one or more light emitting layers; a second stack comprising at least one light emitting layer; and one or more charge generation layers provided between the first stack and the second stack.

According to another exemplary embodiment of the present specification, the organic material layer includes: a first stack including one or more light emitting layers; a second stack comprising at least one light emitting layer; and a third stack including one or more light emitting layers, between the first stack and the second stack; and one or more charge generating layers, respectively, between the second stack and the third stack.

In the present specification, the charge generating layer (Charge Generating layer) means a layer in which holes and electrons are generated when a voltage is applied. The charge generation layer may be an N-type charge generation layer or a P-type charge generation layer. As used herein, the N-type charge generation layer refers to a charge generation layer located closer to the anode than the P-type charge generation layer, and the P-type charge generation layer refers to a charge generation layer located closer to the cathode than the N-type charge generation layer.

The N-type charge generation layer and the P-type charge generation layer may be provided in contact with each other, and in this case, an NP junction is formed. By the NP junction, holes are easily formed in the P-type charge generation layer and electrons are easily formed in the N-type charge generation layer. Electrons are transported in the anode direction through the LUMO level of the N-type charge generating layer, and holes are transported in the cathode direction through the HOMO level of the P-type organic material layer.

The first stack, the second stack, and the third stack each include one or more light emitting layers, and further include a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole blocking layer, a hole transport and a hole It may further include one or more layers of a layer for simultaneous injection (a hole injection and transport layer), and a layer for simultaneously performing an electron transport and electron injection (electron injection and transport layer).

An organic light emitting diode including the first stack and the second stack is illustrated in FIG. 3 .

3 shows a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, an electron blocking layer 5, a first light emitting layer 6a, a first electron transport layer 9a, An N-type charge generation layer 12, a P-type charge generation layer 13, a second hole transport layer 4b, a second light emitting layer 6b, an electron injection and transport layer 8, and a cathode 11 are sequentially stacked The structure of the organic light emitting device is exemplified. In such a structure, the compound represented by Chemical Formula 1 may be included in the first emission layer 6a or the second emission layer 6b, and the compound represented by Chemical Formula 2 is the first electron transport layer 9a or electron injection. and the transport layer 8 .

The organic light emitting diodes including the first to third stacks are illustrated in FIGS. 4 to 7 .

4 shows a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, an electron blocking layer 5, a first light emitting layer 6a, a first electron transport layer 9a, The first N-type charge generation layer 12a, the first P-type charge generation layer 13a, the second hole transport layer 4b, the second light-emitting layer 6b, the second electron transport layer 9b, the second N-type charge An organic layer in which the generation layer 12b, the second P-type charge generation layer 13b, the third hole transport layer 4c, the third light emitting layer 6c, the third electron transport layer 9c and the cathode 11 are sequentially stacked The structure of the light emitting device is illustrated. In such a structure, the compound represented by Formula 1 may be included in the first light emitting layer 6a, the second light emitting layer 6b, and the third light emitting layer 6c, and the compound represented by Formula 2 is the first electron It may be included in one or more layers of the transport layer 9a, the second electron transport layer 9b, and the third electron transport layer 9c.

5 shows a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light emitting layer 6BFa, a first electron transport layer ( 9a), first N-type charge generation layer 12a, first P-type charge generation layer 13a, third hole transport layer 4c, red phosphorescence emission layer 6RP, yellow green phosphorescence emission layer 6YGP, green phosphorescence Light emitting layer 6GP, second electron transport layer 9b, second N-type charge generation layer 12b, second P-type charge generation layer 13b, fourth hole transport layer 4d, fifth hole transport layer 4e , the second blue fluorescent light emitting layer 6BFb, the third electron transport layer 9c, the electron injection layer 10, the cathode 11, and the capping layer 14 are sequentially stacked, the structure of the organic light emitting device is exemplified. In such a structure, the compound represented by Chemical Formula 1 may be included in the first blue fluorescent light emitting layer 6BFa or the second blue fluorescent light emitting layer 6BFb, and the compound represented by Chemical Formula 2 is the first electron transport layer 9a. ) or may be included in the third electron transport layer 9c.

6 shows a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light emitting layer 6BFa, a first electron transport layer ( 9a), the first N-type charge generation layer 12a, the first P-type charge generation layer 13a, the third hole transport layer 4c, the red phosphorescent emission layer 6RP, the green phosphorescence emission layer 6GP, the second electrons Transport layer 9b, second N-type charge generation layer 12b, second P-type charge generation layer 13b, fourth hole transport layer 4d, fifth hole transport layer 4e, second blue fluorescent light emitting layer 6BFb ), the third electron transport layer 9c, the electron injection layer 10, the cathode 11, and the capping layer 14 are sequentially stacked, the structure of the organic light emitting device is exemplified. In such a structure, the compound represented by Chemical Formula 1 may be included in the first blue fluorescent light emitting layer 6BFa or the second blue fluorescent light emitting layer 6BFb, and the compound represented by Chemical Formula 2 is the first electron transport layer 9a. ) or may be included in the third electron transport layer 9c.

7 shows a substrate 1, an anode 2, a first p-doped hole transport layer 4pa, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light emitting layer 6BFa, The first electron transport layer 9a, the first N-type charge generation layer 12a, the first P-type charge generation layer 13a, the third hole transport layer 4c, the fourth hole transport layer 4d, the second blue fluorescence Light emitting layer 6BFb, second electron transport layer 9b, second N-type charge generation layer 12b, second P-type charge generation layer 13b, fifth hole transport layer 4e, sixth hole transport layer 4f , the third blue fluorescent light emitting layer 6BFc, the third electron transport layer 9c, the electron injection layer 10, the cathode 11, and the capping layer 14 are sequentially stacked, the structure of the organic light emitting device is exemplified. In such a structure, the compound represented by Formula 1 may be included in one or more layers of the first blue fluorescent light-emitting layer 6BFa, the second blue fluorescent light-emitting layer 6BFb, and the third blue fluorescent light-emitting layer 6BFb, The compound represented by Chemical Formula 2 may be included in one or more of the first electron transport layer 9a, the second electron transport layer 9c, and the third electron transport layer 9c.

The N-type charge generation layer is 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), fluorine-substituted 3,4,9,10-pe Lylenetetracarboxylic dianhydride (PTCDA), cyano-substituted PTCDA, naphthalenetetracarboxylic dianhydride (NTCDA), fluorine-substituted NTCDA, cyano-substituted NTCDA, hexaazatriphenylline derivatives and the like, but is not limited thereto. In an exemplary embodiment, the N-type charge generation layer may include a benzimidazophenanthrine-based derivative and a metal of Li at the same time.

The P-type charge generation layer may include an arylamine-based derivative and a compound including a cyano group at the same time.

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 deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate. to form an anode, and after forming an organic material layer including the above-described first organic material layer and the second organic material layer thereon, it can be manufactured by depositing a material that can be used as a cathode thereon. In addition to this method, an organic electronic 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 including the first organic material layer and the second organic material layer is a hole injection layer, a hole transport layer, an electron injection and electron transport layer at the same time, an electron suppression layer, a light emitting layer, an electron transport layer, an electron injection layer, electron injection and electron transport at the same time It may be a multi-layer structure further comprising a layer, a hole-blocking layer, and the like. In addition, the organic layer is formed using a variety of polymer materials in a smaller number by a solvent process rather than a vapor deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.

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

The cathode is an electrode for injecting electrons, and the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer that facilitates injection of holes from the anode to the light emitting layer. As the hole injection material, holes can be well injected from the anode at a low voltage, and the highest occupied (HOMO) of the hole injection material is The molecular orbital) is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto.

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

The hole transport layer and/or hole injection layer material known in the art may be used for the hole transport layer and hole injection layer at the same time.

For the layer that simultaneously transports and injects electrons, an electron transport layer material and/or an electron injection layer material known in the art may be used.

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. For the electron-blocking layer, a material known in the art may be used.

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 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

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

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

A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and a material known in the art may be used.

The electron transport layer serves to facilitate the transport of electrons. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high electron mobility is suitable. Specific examples include 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 injection layer serves to facilitate electron injection. As the electron injection material, a compound having an ability to transport electrons, an electron injection effect from the cathode, an excellent electron injection effect for a light emitting layer or a light emitting material, and an excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

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

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

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

Preparation Example 1. Synthesis of BH-1

Synthesis of Intermediate 1 and Intermediate 2

2-Bromoanthracene (100 g), 1-naphthylboronic acid (1.2 equivalents), and potassium phosphate (2.5 equivalents) were dissolved in 1 L of dioxane and 300 mL of water, followed by heating and stirring. Bis(tritertibutylphosphine)palladium (0.002 equivalent) was dissolved in a small amount of dioxane and added dropwise, followed by termination after 1 hour. After cooling, the water layer was removed and the organic layer was concentrated under reduced pressure. Recrystallization using toluene and ethanol to obtain Intermediate 1 (yield 92%)

Intermediate 1 (90 g) was dissolved in 720 mL of DMF and cooled to 0°C. N-bromosuccinimide (NBS, 1.05 equiv) was slowly added dropwise, followed by further stirring for 30 minutes. After completion of the reaction, 1 L of toluene was added, and the organic layer was washed three times with water. Concentrated under reduced pressure and recrystallized using ethanol and hexane to obtain Intermediate 2 (yield 67%).

Synthesis of Intermediate 3 and Intermediate 4

Intermediate 3 was synthesized in the same manner as in the synthesis of Intermediate 1, except that Intermediate 2 (40 g) and d5-phenylboronic acid were used instead of 2-bromoanthracene and 1-naphthylboronic acid (yield 82%) .

Intermediate 4 was synthesized in the same manner as in the synthesis of Intermediate 2, except that Intermediate 3 (25 g) was used instead of Intermediate 1 (yield 88%).

Synthesis of BH-1

Compound BH-1 was synthesized in the same manner as in the synthesis of Intermediate 1, except that Intermediate 4 (20 g) and phenylboronic acid were used instead of 2-bromoanthracene and 1-naphthylboronic acid (yield 71%) .

In Preparation Example 1, the following compounds BH-2 to BH-5 can be synthesized by changing the intermediate.

Preparation Example 2. Synthesis of ETL-1

2-chloro-4- (naphthalen-2-yl) -6-phenyl-1,3,5-triazine (20 g) and spiro [fluorene-9,9'-xanthene] -2-ylboronic acid 2 - Compound ETL-1 was synthesized in the same manner as in the synthesis of Intermediate 1, except that -bromoanthracene and 1-naphthylboronic acid were used instead (yield 61%).

In Preparation Example 2, ETL-2 to ETL-38 can be synthesized by changing the intermediate.

Manufacturing of organic light emitting devices

Comparative Example 1

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,500 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, 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 washing 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, hexanitrile hexaazatriphenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 500 Å to form a hole injection layer.

(HAT)

(HAT)

4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (400 Å) of the following formula, which is a material for transporting holes, on the hole injection layer was vacuum deposited to form a hole transport layer formed.

(NPB)

(NPB)

Then, 2-(naphthalen-1-yl)-10-phenyl-9-(phenyl-d5)anthracene (BH-1) as a light emitting layer host was vacuum-deposited to a thickness of 300 Å on the hole transport layer to form an emission layer.

(BH-1)

(BH-1)

While depositing the light emitting layer, the material (BD-A) having the following structure was used as a blue light emitting dopant relative to the total weight of the light emitting layer. 2 wt% was used.

(BD-A)

(BD-A)

On the emission layer, a material (ETL-A) having the following structure was vacuum deposited to a thickness of 200 Å to form an electron injection and transport layer.

(ETL-A)

(ETL-A)

A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 2,000 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 0.7 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 2×10 ^-7 to 5×10 ^-8 torr was maintained.

Comparative Examples 2 to 4

An organic light emitting diode was manufactured in the same manner as in Comparative Example 1, except that compounds of the following ETL-B, ETL-C, or ETL-D were respectively used instead of ETL-A in Comparative Example 1.

Example 1

An organic light emitting diode was manufactured in the same manner as in Comparative Example 1, except that the compound of ETL-1 below was used instead of ETL-A in Comparative Example 1.

(ETL-1)

(ETL-1)

Comparative Examples 5 to 8

In Comparative Example 1, the compounds of ETL-B, ETL-C, or ETL-D were respectively used instead of ETL-A, and ETL-1 was used instead of ETL-A. A light emitting device was fabricated.

Preparation of Examples 2 to 5

An organic light emitting diode was manufactured in the same manner as in Example 1, except that in Example 1, the compounds of BH-2, BH-3, BH-4, or BH-5 in the table below were used instead of BH-1.

Preparation of Examples 6 to 42

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compounds of ETL-2 to ETL-38 in the following table were used instead of ETL-1 in Example 1.

Table 1 shows the results of testing the organic light emitting devices prepared in Comparative Examples 1 to 8 and Examples 1 to 42 at a current density of 20 mA/cm ² .

small example light emitting layer host electron injection and transport layer Driving voltage (V) Luminous Efficiency (Cd/A) Life T97% (hours) Comparative Example 1 BH-1 ETL-A 4.29 6.60 80 Comparative Example 2 BH-1 ETL-B 4.21 6.54 65 Comparative Example 3 BH-1 ETL-C 4.31 6.44 82 Comparative Example 4 BH-1 ETL-D 4.19 6.57 54 Comparative Example 5 BH-A ETL-1 4.15 6.82 92 Comparative Example 6 BH-B ETL-1 4.39 6.75 69 Comparative Example 7 BH-C ETL-1 4.42 6.60 58 Comparative Example 8 BH-D ETL-1 4.22 6.45 74 Example 1 BH-1 ETL-1 4.16 6.80 130 Example 2 BH-2 ETL-1 4.17 6.77 124 Example 3 BH-3 ETL-1 4.15 6.79 148 Example 4 BH-4 ETL-1 4.15 6.76 176 Example 5 BH-5 ETL-1 4.16 6.78 184 Example 6 BH-1 ETL-2 4.08 6.94 106 Example 7 BH-1 ETL-3 4.20 6.73 144 Example 8 BH-1 ETL-4 4.15 6.96 104 Example 9 BH-1 ETL-5 4.16 6.99 98 Example 10 BH-1 ETL-6 4.12 6.95 104 Example 11 BH-1 ETL-7 4.14 6.79 132 Example 12 BH-1 ETL-8 4.05 6.86 119 Example 13 BH-1 ETL-9 4.12 6.80 131 Example 14 BH-1 ETL-10 4.19 6.71 148 Example 15 BH-1 ETL-11 4.14 6.94 107 Example 16 BH-1 ETL-12 4.18 6.87 117 Example 17 BH-1 ETL-13 4.10 6.88 116 Example 18 BH-1 ETL-14 4.14 6.76 139 Example 19 BH-1 ETL-15 3.99 6.87 117 Example 20 BH-1 ETL-16 4.12 6.91 111 Example 21 BH-1 ETL-17 3.98 6.95 104 Example 22 BH-1 ETL-18 4.19 6.92 108 Example 23 BH-1 ETL-19 4.17 6.71 148 Example 24 BH-1 ETL-20 4.12 6.73 145 Example 25 BH-1 ETL-21 4.15 6.92 109 Example 26 BH-1 ETL-22 4.16 6.97 101 Example 27 BH-1 ETL-23 4.03 6.60 175 Example 28 BH-1 ETL-24 4.02 6.73 145 Example 29 BH-1 ETL-25 4.08 6.67 158 Example 30 BH-1 ETL-26 4.16 6.89 114 Example 31 BH-1 ETL-27 4.13 6.63 166 Example 32 BH-1 ETL-28 4.13 6.93 108 Example 33 BH-1 ETL-29 3.99 6.99 99 Example 34 BH-1 ETL-30 4.16 6.83 125 Example 35 BH-1 ETL-31 4.15 6.60 174 Example 36 BH-1 ETL-32 3.98 6.99 98 Example 37 BH-1 ETL-33 4.12 6.93 108 Example 38 BH-1 ETL-34 4.08 6.77 135 Example 39 BH-1 ETL-35 4.02 6.72 147 Example 40 BH-1 ETL-36 4.04 6.92 110 Example 41 BH-1 ETL-37 3.98 6.91 110 Example 42 BH-1 ETL-38 4.08 6.74 143

Therefore, when the compound of Formula 1 of the present invention is used as the host of the light emitting layer and the compound of Formula 2 is used as an electron transport layer, electron injection layer or electron injection and transport layer, the low voltage and high efficiency characteristics of Formula 1 and the above-described Formula 2 It can be seen that an organic light-emitting device with improved stability can be obtained by securing thermal stability due to long life characteristics and high glass transition temperature.

1: substrate / 2: anode / 3: hole injection layer / 4: hole transport layer / 4a: first hole transport layer / 4b: second hole transport layer / 4c: third hole transport layer / 4d: fourth hole transport layer / 4e: second 5 hole transport layer / 4f: sixth hole transport layer / 4p: p-doped hole transport layer / 4R: red hole transport layer / 4G: green hole transport layer / 4B: blue hole transport layer / 5: electron blocking layer / 6: light emitting layer / 6a: First light-emitting layer/6b: second light-emitting layer/ 6c: third light-emitting layer/ 6BF: blue fluorescent light-emitting layer/ 6BFa: first blue fluorescent light-emitting layer/ 6BFb: second blue fluorescent light-emitting layer/ 6YGP: yellow green phosphorescent light-emitting layer/ 6RP: red phosphorescent light-emitting layer / 6GP: green phosphorescent light emitting layer/ 7: hole blocking layer/ 8: electron injection and transport layer/ 9: electron transport layer/ 9a: first electron transport layer/ 9b: second electron transport layer/ 9c: third electron transport layer/ 10: electron injection Layer/ 11: cathode/ 12: N-type charge generation layer/ 12a: first N-type charge generation layer/ 12b: second N-type charge generation layer/ 13: P-type charge generation layer/ 13a: first P-type charge generation Layer/ 13b: second P-type charge generation layer/ 14: capping layer

Claims (13)

anode; cathode; and an organic material layer provided between the anode and the cathode,
The organic layer includes a first organic layer including a compound represented by the following formula (1) and a second organic layer including a compound represented by the following formula (2),
The second organic material layer is provided in contact with the first organic material layer,
The first organic material layer is a light emitting layer,
The second organic layer is an electron transport layer,
The energy of the light emitting layer and the electron transport layer satisfies the following formula (1),
Equation (1): G _ETL - G _EML > 0.0 eV
In Equation (1), G _EML refers to S0-S1/S0 Gap in the light emitting layer (EML), and G _ETL refers to S0-S1/S0 Gap in the electron transport layer (ETL),
The electron affinity (E _EML ) of the light emitting layer and the electron affinity (E _ETL ) of the electron transport layer are organic light emitting devices that satisfy the following formula (2):
Equation (2): E _ETL - E _EML > 0.2 eV
[Formula 1]

In Formula 1,
Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group,
At least one of Ar1 and Ar2 contains deuterium,
Ar3 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
L1 to L3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; halogen group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
r1 is an integer of 0 to 4, and when r1 is 2 or more, R1 of 2 or more are the same as or different from each other,
r2 is an integer of 0 to 3, and when r2 is 2 or more, 2 or more R2 are the same as or different from each other,
[Formula 2]

In Formula 2,
Y is O; or S;
1 to 4 of G1 to G16 are connected to Formula 3 below,
The remainder not connected to Formula 3 among G1 to G16 is hydrogen; or deuterium, or adjacent substituents combine with each other to form a substituted or unsubstituted benzene ring,
[Formula 3]

In Formula 3,
X1 is N or C(R31), X2 is N or C(R32), X3 is N or C(R33), and at least one of X1 to X3 is N,
Ar21 and Ar22 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with adjacent R31, R32 or R33 to form a substituted or unsubstituted ring,
R31, R32 and R33 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or combined with adjacent Ar21 or Ar22 to form a substituted or unsubstituted ring,
L4 is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

is a position connected to Formula 2 above. delete The method according to claim 1,
The compound represented by Formula 1 is an organic light emitting device included as a host. The method according to claim 1,
The organic material layer includes two or more light emitting layers, and one of the two or more light emitting layers is the first organic material layer. 5. The method according to claim 4,
The organic light emitting device of which the maximum emission peaks of the two or more light emitting layers are different from each other. 5. The method according to claim 4,
The first organic material layer is an organic light emitting device comprising a fluorescent dopant. The method according to claim 1,
Formula 3 is an organic light emitting device represented by any one of the following Formulas 301 to 303:
[Formula 301]

[Formula 302]

[Formula 303]

In Formulas 301 to 303,
The definition of L4 is as defined in Formula 3,
X1 to X3 are the same as or different from each other, each independently represent N or CH, and at least one of X1 to X3 is N,
Ar23 and Ar24 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R34 is hydrogen; heavy hydrogen; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
r34 is an integer of 0 to 4, and when r34 is 2 or more, R34 is the same as or different from each other. The method according to claim 1,
Formula 2 is an organic light emitting device represented by any one of Formulas 2-1 to 2-4:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

In Formulas 2-1 to 2-4,
The definitions of Y, L4, X1 to X3, Ar21 and Ar22 are as defined in Formula 2. The method according to claim 1,
Ar1 and Ar2 are the same as or different from each other, and each independently represent a phenyl group unsubstituted or substituted with deuterium; a biphenyl group unsubstituted or substituted with deuterium; or a naphthyl group unsubstituted or substituted with deuterium. The method according to claim 1,
Ar21 and Ar22 are the same as or different from each other and each independently represent an aryl group unsubstituted or substituted with R41; Or a heterocyclic group substituted or unsubstituted with R42, or combined with adjacent R31, R32 or R33 to form an aromatic hydrocarbon ring substituted or unsubstituted with R41,
R41 and R42 are the same as or different from each other, and each independently represent deuterium; halogen group; nitrile group; an alkyl group having 1 to 6 carbon atoms; a haloalkyl group having 1 to 6 carbon atoms; an alkoxy group having 1 to 6 carbon atoms; an alkylsilyl group having 1 to 20 carbon atoms; an arylsilyl group having 6 to 30 carbon atoms; an aryl group having 6 to 20 carbon atoms; and one selected from the group consisting of a heterocyclic group having 2 to 20 carbon atoms, or a substituent to which two or more groups selected from the group are connected. The method according to claim 1,
L4 is a direct bond; phenylene group; biphenylene group; terphenylene group; naphthylene group; anthracenylene group; a divalent phenanthrenyl group; a divalent triphenylene group; a divalent fluoranthenyl group; a divalent phenalene group; a divalent fluorenyl group; a divalent dimethyl fluorenyl group; a divalent carbazole group; a divalent phenylcarbazole group; a divalent benzocarbazole group; a divalent indenocarbazole group; a divalent dibenzothiophene group; a divalent dibenzofuran group; divalent dibenzocyrol group; divalent phenoxazine; a divalent phenothiazine group; divalent phenazine group; a divalent acridine group; divalent dihydrophenazine group; a divalent dihydroacridine group; a divalent pyridyl group; a divalent pyrimidyl group; a divalent quinoline group; a divalent isoquinoline group; a divalent quinazoline group; a divalent pyridopyrimidine group; a divalent pyridopyrazine group; bivalent pyrimidoindol; or a divalent pyridoindole group, wherein L4 is a nitrile group; an alkyl group having 1 to 10 carbon atoms; an aryl group having 6 to 30 carbon atoms; and one substituent selected from the group consisting of a heterocyclic group having 2 to 30 carbon atoms, or an organic light-emitting device that is unsubstituted or substituted with a divalent substituent to which two or more groups selected from the group are connected. The organic light-emitting device according to claim 1, wherein the compound represented by Formula 1 is any one selected from the following compounds:

. The organic light-emitting device according to claim 1, wherein the compound represented by Formula 2 is any one selected from the following compounds:

.

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