KR20220125018A - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a compound and an organic light emitting device including the same. An exemplary embodiment of the present specification provides a compound represented by chemical formula 1. The organic light emitting device using the compound according to the exemplary embodiment of the present application can have low driving voltage, high luminous efficiency, or long lifespan.

Description

Compound and organic light emitting device including the same

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

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including a first electrode and a second electrode and an organic material layer therebetween. Here, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. 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 at the first electrode and electrons are injected into the organic material layer at the second electrode, and excitons are formed when the injected holes and electrons meet. , when this exciton falls back to the ground state, it glows.

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

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

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

[Formula 1]

In Formula 1,

X is O or S;

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; nitro group; hydroxyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r is an integer from 1 to 4, r1 is an integer from 1 to 8, r2 is an integer from 1 to 6,

When r is 2 or more, Ar is the same as or different from each other,

When r1 is 2 or more, R1 is the same as or different from each other,

When r2 is 2 or more, R2 are the same as or different from each other,

L1 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,

L2 is a direct bond, a substituted or unsubstituted r+1 valent aryl group, or a substituted or unsubstituted r+1 valent heterocyclic group,

Ar is a substituent of formula A,

[Formula A]

In the above formula (A),

Y is O or S;

A1 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; nitro group; hydroxyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a1 is an integer from 1 to 7,

When a1 is 2 or more, A1 is the same as or different from each other,

* is a position bonded to Formula 1,

when L1 is a direct bond, L2 is a substituted or unsubstituted r+1 valent aryl group, or a substituted or unsubstituted r+1 valent heterocyclic group; A1 is a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

In addition, an exemplary embodiment of the present specification includes a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the compound according to any one of claims 1 to 8. provide the element.

The organic light emitting device using the compound according to an exemplary embodiment of the present application can have a low driving voltage, high luminous efficiency, or a long lifespan.

1 illustrates a structure of an organic light emitting diode according to an exemplary embodiment.
2 illustrates a structure of an organic light emitting diode according to another exemplary embodiment.
3 illustrates a structure of an organic light emitting device according to another exemplary embodiment.

Hereinafter, the present specification will be described in detail.

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

Formula 1 of the present invention includes a naphthooxazolyl group or a naphthothiazolyl group of a condensed aryl group such as naphthyl, thereby improving the hole and electron injection, transport, and control characteristics of the anthracene derivative and further optimizes the carrier balance in the light emitting layer. can

Formula 1 of the present invention has an aromatic naphthooxazolyl group or naphthothiazolyl group containing a heteroatom, and improves the hole injection and transport ability as a host of the blue light emitting layer by binding to the anthracene parent nucleus, thereby increasing the carrier concentration inside the light emitting layer It is possible to increase the luminous efficiency by increasing and balancing the injected electrons. In particular, it was intended to show the effect of lowering the driving voltage by drawing a compound structure through the combination with Chemical Formula A.

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

In the present specification, * or a dotted line refers to a site bonded or condensed to another substituent or a bonding portion.

In the present specification, Cn means that the number of carbon atoms is n, and Cn-Cm means that the number of carbon atoms is n to m.

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 in which the substituent is substitutable, is 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); silyl group; boron group; an alkyl group; cycloalkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, is substituted with a substituent to which two or more of the above exemplified substituents are connected, or does not have any substituents. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.

In an exemplary embodiment of the present specification, "substituted or unsubstituted" is deuterium; halogen group; cyano group (-CN); silyl group; C1-C20 alkyl group; C3-C60 cycloalkyl group; C6-C60 aryl group; And it means that it is substituted with one or more substituents selected from the group consisting of a C2-C60 heterocyclic group, is substituted with a substituent to which two or more groups selected from the group are connected, or does not have any substituents.

In an exemplary embodiment of the present specification, "substituted or unsubstituted" is deuterium; halogen group; cyano group (-CN); silyl group; C1-C10 alkyl group; C3-C30 cycloalkyl group; C6-C30 aryl group; And it means that it is substituted with one or more substituents selected from the group consisting of a C2-C30 heterocyclic group, is substituted with a substituent to which two or more groups selected from the group are connected, or does not have any substituents.

In an exemplary embodiment of the present specification, "substituted or unsubstituted" is deuterium; halogen group; cyano group (-CN); silyl group; C1-C6 alkyl group; C3-C20 cycloalkyl group; C6-C20 aryl group; And it means that it is substituted with one or more substituents selected from the group consisting of a C2-C20 heterocyclic group, is substituted with a substituent to which two or more groups selected from the group are connected, or does not have any substituents.

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 replaced with another substituent. For example, an isopropyl group and a phenyl group are linked

or

may be a substituent of

또는

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

or

may 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 substituted with A and B.

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

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

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

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

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

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

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

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, and the like, 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 substituted aryl group may include a form in which an aliphatic ring is condensed to an aryl group. For example, a tetrahydronaphthalene group or a dihydroindene group of the following structure is included in a substituted aryl group. In the following structure, one of the carbons of the benzene ring may be linked to another position.

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 alkylaryl group refers to an aryl group substituted with an alkyl group, and a substituent other than the alkyl group may be further connected.

In the present specification, the arylalkyl group refers to an alkyl group substituted with an aryl group, and a substituent other than the alkyl group may be further connected.

In the present specification, an aryloxy group is an aryl group connected to an oxygen atom, an arylthio group is an aryl group connected to a sulfur atom, and the description of the aryl group described above can be applied to the aryl group of the aryloxy group and the arylthio group. The aryl group of the aryloxy group is the same as the example of the aryl group described above. Specifically, the aryloxy group includes a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group, etc., and the arylthioxy group includes phenylthioxy group, 2- and a methylphenylthioxy group, a 4-tert-butylphenylthioxy group, and the like, but are not limited thereto.

In the present specification, the heterocyclic group is a cyclic group including at least one of N, O, P, S, Si and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of the heterocyclic group include a pyridyl group; quinoline group; thiophene group; dibenzothiophene group; furan group; dibenzofuran group; naphthobenzofuran group; carbazole group; benzocarbazole group; naphthobenzothiophene group; dibenzosilole group; naphthobenzosilole group; hexahydrocarbazole group; dihydroacridine group; dihydrodibenzoazacillin group; phenoxazine; phenothiazine; dihydrodibenzoazacillin group; spiro (dibenzosilol-dibenzoazacillin) groups; Spiro (acridine-fluorene) groups and the like, but are not limited thereto.

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

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

In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.

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

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

In the present specification, an alkylamine group; N-alkylarylamine group; arylamine group; N-aryl heteroarylamine group; The alkyl group, the aryl group and the heteroaryl group in the N-alkylheteroarylamine group and the heteroarylamine group are the same as the examples of the alkyl group, the aryl group and the heteroaryl group, respectively.

In the present specification, the aromatic hydrocarbon ring refers to a hydrocarbon ring in which pi electrons are completely conjugated and planar, and the description of the aryl group can be applied, except that it is divalent.

In the present specification, the aliphatic hydrocarbon ring is a structure bound to a ring, and refers to a non-aromatic ring. Examples of the aliphatic hydrocarbon ring include cycloalkyl or cycloalkane, and the description of the above-described cycloalkyl group or cycloalkenyl group may be applied, except that it is divalent. The substituted aliphatic hydrocarbon ring also includes an aliphatic hydrocarbon ring in which an aromatic ring is condensed.

In the present specification, the condensed ring of the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring means that the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring form a condensed ring. Examples of the aromatic and aliphatic condensed rings include, but are not limited to, a 1,2,3,4-tetrahydronaphthalene group and a 2,3-dihydro-1H-indene group.

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

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

In the present specification, "a 5-membered or 6-membered ring formed by bonding adjacent groups" means that a ring including a substituent participating in ring formation is a 5-membered or 6-membered ring. It may include condensing an additional ring to the ring including the substituents participating in the ring formation.

In an exemplary embodiment of the present specification, Chemical Formula 1 may be the following Chemical Formula 2 or 3.

[Formula 2]

[Formula 3]

In Formulas 2 and 3, R1, R2, Ar, r, r1, r2, L1 and L2 are the same as defined in Formula 1.

In the exemplary embodiment of the present specification, Chemical Formula 1 may be the following Chemical Formula 2-1, 2-2, 3-1, or 3-2.

[Formula 2-1]

[Formula 2-2]

[Formula 3-1]

[Formula 3-2]

In Formulas 2-1, 2-2, 3-1, and 3-2, R1, R2, Ar, r, r1, r2, L1, and L2 have the same definitions as in Formula 1.

In an exemplary embodiment of the present specification, Chemical Formula 1 is the following Chemical Formulas 2-1-1, 2-1-2, 2-1-3, 2-2-1, 2-2-2, 2-2-3 , 3-1-1, 3-1-2, 3-1-3, 3-2-1, 3-2-2 or 3-2-3.

[Formula 2-1-1]

[Formula 2-1-2]

[Formula 2-1-3]

[Formula 2-2-1]

[Formula 2-2-2]

[Formula 2-2-3]

[Formula 3-1-1]

[Formula 3-1-2]

[Formula 3-1-3]

[Formula 3-2-1]

[Formula 3-2-2]

[Formula 3-2-3]

Formula 2-1-1, 2-1-2, 2-1-3, 2-2-1, 2-2-2, 2-2-3, 3-1-1, 3-1-2, In 3-1-3, 3-2-1, 3-2-2 and 3-2-3, R1, R2, Ar, r, r1, r2, L1 and L2 are as defined in Formula 1,

R3 and R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; nitro group; hydroxyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r4 is an integer from 1 to 5,

When r4 is 2 or more, R4 is the same as or different from each other.

In the exemplary embodiment of the present specification, Chemical Formula 1 may be any one of Chemical Formulas 4 to 24 below.

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

[Formula 22]

[Formula 23]

[Formula 24]

In Formulas 4 to 24, X, R1, R2, Ar, r, r1, r2, L1 and L2 are the same as defined in Formula 1,

R3 and R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; nitro group; hydroxyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r4 is an integer from 1 to 5,

When r4 is 2 or more, R4 is the same as or different from each other.

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

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

In an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; halogen group; cyano group; nitro group; hydroxyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, R1 is hydrogen or deuterium.

In an exemplary embodiment of the present specification, R2 is hydrogen; heavy hydrogen; halogen group; cyano group; nitro group; hydroxyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, R2 is hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, R2 is hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted C1-C20 cycloalkyl group; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R2 is hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 10 alkyl group; a substituted or unsubstituted C1-C10 cycloalkyl group; a substituted or unsubstituted C 6 to C 20 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

In an exemplary embodiment of the present specification, R2 is hydrogen; heavy hydrogen; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted cyclopentyl group; a substituted or unsubstituted cyclohexyl group; a substituted or unsubstituted adamantyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted furanyl group; a substituted or unsubstituted thiophenyl group; a substituted or unsubstituted benzofuranyl group; Or a substituted or unsubstituted benzothiophenyl group.

In an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; halogen group; cyano group; nitro group; hydroxyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted C1-C20 cycloalkyl group; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 10 alkyl group; a substituted or unsubstituted C1-C10 cycloalkyl group; a substituted or unsubstituted C 6 to C 20 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

In an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted cyclopentyl group; a substituted or unsubstituted cyclohexyl group; a substituted or unsubstituted adamantyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted furanyl group; a substituted or unsubstituted thiophenyl group; a substituted or unsubstituted benzofuranyl group; Or a substituted or unsubstituted benzothiophenyl group.

In an exemplary embodiment of the present specification, R4 is hydrogen; heavy hydrogen; halogen group; cyano group; nitro group; hydroxyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, R4 is hydrogen; heavy hydrogen; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, R4 is hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, R4 is hydrogen or deuterium.

In an exemplary embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group.

In an exemplary embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, L1 is 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 an unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group.

In an exemplary embodiment of the present specification, L2 is a direct bond, a substituted or unsubstituted r+1 valent aryl group, or a substituted or unsubstituted r+1 valent heterocyclic group.

In an exemplary embodiment of the present specification, L2 is a direct bond, a substituted or unsubstituted, r+1 valent arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted and r+1 valent heterocyclic group having 2 to 30 carbon atoms. .

In an exemplary embodiment of the present specification, L2 is a direct bond, a substituted or unsubstituted, r+1 valent arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted and r+1 valent heterocyclic group having 2 to 20 carbon atoms. .

In an exemplary embodiment of the present specification, L2 is a direct bond, a substituted or unsubstituted r+1 valent phenyl group, a substituted or unsubstituted r+1 valent biphenyl group, a substituted or unsubstituted r+1 valent terphenyl group, substituted or an unsubstituted r+1 valent naphthyl group, a substituted or unsubstituted r+1 valent fluorenyl group, a substituted or unsubstituted r+1 valent phenanthrenyl group, or a substituted or unsubstituted r+1 valent dibenzofuranyl group , or a substituted or unsubstituted r+1 valent dibenzothiophenyl group.

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

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

In an exemplary embodiment of the present specification, A1 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; nitro group; hydroxyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, A1 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, A1 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, A1 is hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted C1-C20 cycloalkyl group; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, A1 is hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 10 alkyl group; a substituted or unsubstituted C1-C10 cycloalkyl group; a substituted or unsubstituted C 6 to C 20 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

In an exemplary embodiment of the present specification, A1 is hydrogen; heavy hydrogen; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted cyclopentyl group; a substituted or unsubstituted cyclohexyl group; a substituted or unsubstituted adamantyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted furanyl group; a substituted or unsubstituted thiophenyl group; a substituted or unsubstituted benzofuranyl group; Or a substituted or unsubstituted benzothiophenyl group.

In an exemplary embodiment of the present specification, A1 is hydrogen; heavy hydrogen; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted 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 furanyl group; a substituted or unsubstituted thiophenyl group; a substituted or unsubstituted benzofuranyl group; Or a substituted or unsubstituted benzothiophenyl group.

In an exemplary embodiment of the present specification, when L1 is a direct bond, L2 is a substituted or unsubstituted r+1 valent aryl group, or a substituted or unsubstituted r+1 valent heterocyclic group. In other words, when L1 is a direct bond, L2 is not a direct bond.

In an exemplary embodiment of the present specification, when L1 is a direct bond, A1 is a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted an alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. In other words, when L1 is a direct bond, A1 is at least one substituent other than hydrogen.

The organic compound used in the organic electroluminescent device must have a band gap of 0.5 to 4.0 eV to function as an organic semiconductor, and a band gap energy of at least 2.9 eV is required to exhibit blue color. According to the fluorescence blue emission principle of the host-dopant system, the bandgap of the blue fluorescent host must be larger than the bandgap of the blue fluorescent dopant so that energy transfer occurs smoothly. Therefore, the blue fluorescent host preferably has an energy bandgap of 2.9 eV to 4.0 eV.

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

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

In the present specification, the band gap refers to the difference between the HOMO energy level and the LUMO energy level.

In an exemplary embodiment of the present specification, the deuterium substitution rate of the compound may be 1% to 100%, specifically 40% to 99%. Physicochemical properties such as chemical bond length related to deuterium are different from hydrogen, and in particular, since the elongation amplitude of C-D bonds is smaller than that of C-H bonds, the van der Waals radius of deuterium is smaller than that of hydrogen. It can be shorter and stronger than the C-H bond, and when substituted with deuterium, the energy of the ground state is lowered, and as the bond length of deuterium and carbon is shortened, the molecular hardcore volume is reduced, and thus the electrical It is known that the thin film volume can be increased by reducing electrical polarizability and weakening intermolecular interaction.

This characteristic can reduce the crystallinity of the thin film, that is, it can make an amorphous state, and can be effective for generally increasing OLED lifespan and driving characteristics, and heat resistance can be further improved.

As a prior art related to the organic light emitting compound containing deuterium, in Korean Patent Publication No. 10-1111406, low voltage driving and long lifespan by substituting deuterium for an amine compound containing carbazole or mixing a compound substituted with deuterium A technology for providing a device is described, and in Korean Patent No. 10-1068224, a technology using an anthracene derivative including a phenyl group in which hydrogen in the phenyl group is substituted with deuterium as a host is described.

Here, the deuterium substitution rate may be calculated using a spectrogram obtained by performing mass spectrometry on a material separated by chromatography. Specifically, in a spectrogram obtained by mass analysis of a substance separated by liquid chromatography or gas chromatography according to a sample to be measured, a deuterium substitution rate may be calculated based on a maximum value of a distribution of molecular weights.

In addition, another method for obtaining the deuterium substitution rate can use nuclear magnetic resonance (NMR), specifically, adding DMF as an internal standard, and using the integration ratio in the ¹ H NMR graph to determine the deuterium substitution rate from the integral amount of the total peak can be calculated

In an exemplary embodiment of the present specification, the compound of Formula 1 may have any one of the following structures. Here, at least one of hydrogens in the compound of the following structure may be substituted with deuterium.

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

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

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

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

In an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound. Specifically, the emission layer may include a host and a dopant including the compound.

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

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

In an exemplary embodiment of the present specification, the organic light emitting device includes an anode; a cathode provided to face the anode; and at least one organic material layer provided between the anode and the cathode, wherein the organic material layer includes: a light emitting layer; a hole transport region provided between the light emitting layer and the anode; and an electron transport region provided between the light emitting layer and the cathode, wherein the light emitting layer includes the compound.

In one embodiment of the present specification, the organic material layer of the hole transport region may be one or more selected from the group consisting of a hole transport layer, a hole injection layer, a layer that transports and injects holes at the same time, and an electron blocking layer.

In an exemplary embodiment of the present specification, the organic material layer of the electron transport region may be at least one selected from the group consisting of an electron transport layer, an electron injection layer, a layer for simultaneously transporting and injecting electrons, and a hole blocking layer.

In another exemplary embodiment, the organic light emitting device may be a normal type organic light emitting device in which a first electrode, one or more organic material layers, and a second electrode are sequentially stacked on a substrate.

In another exemplary embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a second electrode, one or more organic material layers, and a first electrode are sequentially stacked on a substrate.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

(18) anode / hole injection layer / hole transport layer / light emitting layer / layer for electron injection and transport at the same time / cathode

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

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

(21) anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/hole blocking layer/layer for simultaneously injecting and transporting electrons/cathode

For example, the structure of the organic light emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 to 3 .

1 illustrates a structure of an organic light emitting device in which a first electrode 2 , an organic material layer 3 , and a second electrode 4 are sequentially stacked on a substrate 1 .

2 is a structure of an organic light emitting device in which a first electrode 2 , a first organic material layer 5 , a light emitting layer 6 , a second organic material layer 7 , and a second electrode 4 are sequentially stacked on a substrate 1 . is exemplified. In such a structure, the compound may be included in the light emitting layer 6 .

2 illustrates an organic light emitting device, and according to the first electrode and the second electrode, the first organic material layer and the second organic material layer may be a hole transport region and an electron transport region, respectively. At this time, the hole transport region means an organic material layer between the anode and the light emitting layer, for example, it includes at least one of a hole injection layer, a hole transport layer and an electron blocking layer, and the electron transport region means an organic material layer between the cathode and the light emitting layer, For example, it includes at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.

3 shows an anode (2-1), a hole injection layer (8), a hole transport layer (9), a light emitting layer (6), an electron control layer (10), an electron transport layer (11), an electron injection layer ( 12) and the cathode 4-1 are sequentially stacked and the structure of the organic light emitting device is exemplified. In such a structure, the compound may be included in the light emitting layer 6 .

The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present specification, that is, the compound.

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

The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound, that is, the compound represented by Formula 1 above.

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

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

In the exemplary embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

In another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

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

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

The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material has the ability to transport holes and has an excellent hole injection effect on the first electrode, the light emitting layer or the light emitting material, and in the light emitting layer A compound that prevents the generated exciton from moving to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the first electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic 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 is a layer that receives holes from the hole injection layer and transports them to the light emitting layer. The hole transport material is a material capable of transporting holes from the first electrode or hole injection layer to the light emitting layer. Mobility for holes This large material 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.

In an exemplary embodiment of the present specification, the light emitting layer includes a host and a dopant.

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, dibenzofuran. derivatives, dibenzothiophene, dibenzothiophene derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

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

In an exemplary embodiment of the present specification, the host includes one or more compounds of Formula 1 herein.

In an exemplary embodiment of the present specification, the host includes a first anthracene derivative substituted with deuterium and a second anthracene derivative unsubstituted with deuterium, and any one of the first anthracene derivative and the second anthracene derivative is and compounds of formula (1).

In the exemplary embodiment of the present specification, when the host of the emission layer includes the first anthracene derivative and the second anthracene derivative, the mass ratio of the first anthracene derivative and the second anthracene derivative is 99:1 to 1:99, 90:10 to 10:90, 80:20 to 20:80, 70:30 to 30:70 or 60:40 to 40:60.

In the exemplary embodiment of the present specification, the first anthracene derivative substituted with deuterium includes the compound of Formula 1 herein.

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

In an exemplary embodiment of the present specification, the dopant used together with the compound of Formula 1 is a fluorescent dopant.

In an exemplary embodiment of the present specification, the dopant used together with the compound of Formula 1 herein includes a pyrene-based compound or a non-pyrene-based compound.

In an exemplary embodiment of the present specification, the bipyrene-based compound used together with the compound of Formula 1 herein includes a boron-based compound.

In an exemplary embodiment of the present specification, the pyrene-based compound used together with the compound of Formula 1 of the present application is a pyrene-based compound in Japanese Patent Registration No. 4205059 (JP 4205059 B2), Japanese Patent Registration No. 4267623 (JP 4267623 B2), Japanese Patent Registration No. 4188401 (JP 4188401 B2), Japanese Patent Registration No. 4848134 (JP 4848134 B2), Japanese Patent Registration No. 6082179 (JP 6082179 B2) and Japanese Patent Registration No. 5587302 (JP 5587302 B2) can be selected and applied from among the compounds exemplified.

In the exemplary embodiment of the present specification, the pyrene-based compound used together with the compound of Formula 1 herein may be a compound of Formula D1 below.

[Formula D1]

In Formula D1, Ar1 to Ar4 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, Ar1 and Ar3 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, Ar1 and Ar3 are the same as or different from each other, and each independently represents an aryl group unsubstituted or substituted with an alkyl group.

In an exemplary embodiment of the present specification, Ar1 and Ar3 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with a methyl group.

In an exemplary embodiment of the present specification, Ar2 and Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, Ar2 and Ar4 are the same as or different from each other, and each independently represent a substituted or unsubstituted dibenzofuranyl group.

In an exemplary embodiment of the present specification, Ar2 and Ar4 are dibenzofuranyl groups.

In the exemplary embodiment of the present specification, Ar1 and Ar3 may be the same as each other.

In an exemplary embodiment of the present specification, Ar2 and Ar4 may be the same as each other.

In an exemplary embodiment of the present specification, the boron-based compound is disclosed in Japanese Patent Registration No. 5935199 (JP 5935199 B2), International Patent Publication No. WO2017-138526A1, Japanese Patent Registration No. 6611825 (JP 6611825 B2), International Patents It can be applied by selecting from among the compounds exemplified in Publication No. WO2018-047639A1, International Patent Publication No. WO2018-110497A1, and Japanese Patent Application Laid-Open No. 2020-097561 (JP 2020-097561 A).

In the exemplary embodiment of the present specification, the pyrene-based compound used together with the compound of Formula 1 herein may be a compound of Formula D2 below.

[Formula D2]

In the formula D2,

Ar5 and Ar6 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

Z1 to Z3 are hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, A substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or groups adjacent to each other combine to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and are each independently an aryl group unsubstituted or substituted with an alkyl group.

In an exemplary embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with a methyl group.

In an exemplary embodiment of the present specification, Z1 to Z3 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group.

In an exemplary embodiment of the present specification, Z1 to Z3 are methyl groups.

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

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

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

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

In an exemplary embodiment of the present specification, the compound is a host, specifically a fluorescent host, and more specifically a blue fluorescent host.

In an exemplary embodiment of the present specification, the maximum emission peak (λ _max ) of the emission layer including the compound represented by Formula 1 is in the range of 400 nm to 470 nm.

In an exemplary embodiment of the present specification, the light emitting layer includes a host and a dopant in a mass ratio of 99:1 to 1:99.

In an exemplary embodiment of the present specification, the light emitting layer includes a host and a dopant in a mass ratio of 99:1 to 10:90.

In an exemplary embodiment of the present specification, the light emitting layer includes a host and a dopant in a mass ratio of 99:1 to 50:50.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. This is suitable. Specific examples include Al complex of 8-hydroxyquinoline; complexes comprising Alq3; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function and followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum layer or a silver layer.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the second electrode, an excellent electron injection effect on the light emitting layer or the light emitting material, and A compound which prevents migration to the hole injection layer and is excellent in the ability to form a thin film is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene 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 hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but is not limited thereto.

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electronic blocking layer may be a material known in the art.

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, the present specification will be described in more detail through examples. However, the following examples are only for illustrating the present specification, and are not intended to limit the present specification.

Preparation Example 1 (Synthesis of A1 to A12)

After dissolving SM1 (1eq) in chloroform (excess) and temperature-stabilizing it at 0 ° C, N-Bromosuccimide (1.00eq) was added to dimethylformamide (DMF, N-bromosuccinimide in volume ratio) 3 times), dissolve and add. After raising the temperature to room temperature and confirming the completion of the reaction, sodium bisulfate aqueous solution (saturated solution) was added, and the layers were separated and extracted. After removal of the solvent, the above formula (A) was prepared by column with ethyl acetate and hexane.

Formulas A1 to A12 of [Table A] were synthesized in the same manner except that SM1 was changed in the synthesis method of Formula A.

[Table A]

Preparation Example 2 (Synthesis of B1 to B29)

Here, X, R2 and r2 are the same as defined in Formula 1.

1) Formula A (leq), SM2 (1.1eq) and pyridine (2eq) were dissolved in chloroform (excess) and heated to reflux. After 2 hours, after confirming the completion of the reaction, it was cooled to room temperature. After extraction by pouring water, it was solidified by recrystallization with chloroform and hexane.

2) The solid was dissolved in copper iodide (0.01eq), 1, 10-phenanthroline (0.2eq), and potassium carbonate (3eq) in DMF (excess), and then heated to reflux. After confirming the completion of the reaction after 2 hours, the mixture was cooled to room temperature, extracted by pouring water, and recrystallized from dichlorobenzene and methyl tert-butyl ether to prepare Formula B.

Formulas B1 to B29 of [Table B] were synthesized in the same manner except that A and SM2 were changed in the synthesis method of Formula B.

[Table B]

Preparation Example 3 (Synthesis of Compounds C1 to C8)

Here, X, R2 r2 and L1 are the same as defined in Formula 1.

Formula B (leq) and SM3 ((1.05eq) of Table C below were added to tetrahydrofuran (THF, excess), and then 2M aqueous potassium carbonate solution (30 volume ratio relative to THF) was added, and tetrakistriphenyl-phosphino After adding palladium (2 mol%) and stirring for 10 hours, the temperature was lowered to room temperature, and after completion of the reaction, the layer was separated by removing the potassium carbonate aqueous solution.Removed the solvent and purified by recrystallization using chloroform and ethanol. Formula C was prepared.

The synthesis of Chemical Formulas C1 to C8 in [Table C] was synthesized in the same manner as in Chemical Formula C, except that B and SM3 were changed.

[Table C]

Preparation Example 4 (Synthesis of Compounds D1 to D30)

Here, X, R2 r2 and L1 are the same as defined in Formula 1.

SM4 (leq) 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) corresponding to formula B or C (1.3 eq) was added to 1,4-dioxane (12 times <mass ratio> compared to SM4), potassium acetate (3eq) was added, and stirred and refluxed. Palladium acetate (0.02eq) and tricyclohexylphosphine (0.04eq) were stirred in 1,4-dioxane for 5 minutes, then added, and after 2 hours, after confirming the completion of the reaction, the mixture was cooled to room temperature. After adding ethanol and water, the mixture was filtered and purified by recrystallization with ethyl acetate and ethanol to prepare Chemical Formula D.

Formulas D1 to D30 of [Table D] were synthesized in the same manner except that SM4 was changed in the synthesis method of Formula D.

[Table D]

Preparation Example 5 (Synthesis of Compounds 1 to 30)

Here, X, R1, R2, r1, r2, Ar, r, L1 and L2 are the same as defined in Formula 1.

After adding the compound of formula D (leq) and the compound of formula SM5 (1.05eq) to tetrahydrofuran (excess, THF), 2M aqueous potassium carbonate solution (30 volume ratio compared to THF) was added, and tetrakistriphenyl-phosphino After adding palladium (2 mol%), the mixture was heated and stirred for 10 hours. After the reaction was terminated by lowering the temperature to room temperature, the potassium carbonate aqueous solution was removed and the layers were separated. After confirming the completion of the reaction, the solvent was removed and the product was purified by recrystallization using toluene.

The syntheses of compounds 1 to 30 of [Table 1] were synthesized in the same manner as in the above products, except that D and SM5 were changed.

Preparation 6 (synthesis of compound 31 to compound 33)

Here, X, R1, R2, r1, r2, Ar, r, L1 and L2 are as defined in Formula 1, D is deuterium, and n is the number of deuterium substituted.

The reactant (1eq), Trifluoromethanesulfonic acid (cat.) was added to C ₆ D ₆ (10-50 times the mass ratio of the reactant) and stirred at 70° C. for 10 to 100 minutes. After completion of the reaction, D ₂ O (excess) was added and stirred for 30 minutes, followed by dropwise addition of trimethylamine (excess). The reaction solution was transferred to a separatory funnel, and extracted with water and chloroform. After drying the extract with MgSO ₄ , toluene was added, heated, and then cooled to obtain compounds 31 to 33 of [Table 2], respectively, through recrystallization.

Deuterium substitution for the above product was carried out with reference to the prior literature of KR 10-1538534 B1, and since the degree of deuterium substitution for each product is different depending on the reaction time, the total reaction time was adjusted to 50 minutes to achieve the maximum m/z ( The substitution rate was determined according to the M+) value.

<Example 1> Preparation of OLED

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

On the prepared anode, HI-1 was thermally vacuum deposited to a thickness of 50 Å to form a hole injection layer, and HT1, a material for transporting holes, was vacuum deposited thereon to a thickness of 1150 Å to form a hole transport layer. Then, a hole control layer was formed using EB1 (150 Å), and then the host compound 1 synthesized in Preparation Example 5 and the dopant BD1 (2 wt %) were vacuum deposited to a thickness of 360 Å to form a light emitting layer. . Thereafter, ET1 was deposited by 50 Å to form an electron control layer, and the compound ET2 and Liq were mixed at a ratio of 7:3 to form an electron transport layer having a thickness of 250 Å. Magnesium and lithium fluoride (LiF) with a thickness of 50 Å were sequentially formed as an electron injection layer <EIL>, and then 200 Å of magnesium and silver (1:4) were formed as an anode. Then, CP1 was deposited with 600 Å to complete the device. In the above process, the deposition rate of the organic material was maintained at 1 Å/sec.

Example 1 which is the experimental result of the organic light emitting device prepared by using the compounds 1 to 33 synthesized in Preparation Examples 5 and 6 and the BH1 to BH10 as the host material of the light emitting layer and BD1 and BD2 as the dopant material of the light emitting layer to 38 and Comparative Examples 1 to 12 are shown in [Table 3].

At this time, the driving voltage and luminous efficiency of the organic light emitting diode were measured at a current density of 20 mA/cm ² , and the time (T95) at which the initial luminance was 95% compared to the initial luminance at a current density of 20 mA/cm ² was measured.

Experimental example
20 mA/cm2 host dopant Voltage (V)
(@20mA/cm ² ) Cd/A
(@20mA/cm ² ) color coordinates
(x,y) life span
(T95, h)
(@20mA/cm ² ) Example 1 compound 1 BD1 3.51 6.63 (0.135, 0.138) 55.8 Example 2 compound 2 BD1 3.40 6.60 (0.134, 0.137) 56.9 Example 3 compound 3 BD1 3.50 6.58 (0.134, 0.137) 54.0 Example 4 compound 4 BD1 3.42 6.63 (0.134, 0.137) 55.1 Example 5 compound 5 BD1 3.53 6.65 (0.136, 0.139) 56.8 Example 6 compound 6 BD1 3.58 6.70 (0.135, 0.138) 58.4 Example 7 compound 7 BD1 3.50 6.69 (0.135, 0.138) 54.1 Example 8 compound 8 BD1 3.39 6.62 (0.134, 0.142) 56.9 Example 9 compound 9 BD1 3.48 6.60 (0.135, 0.141) 59.1 Example 10 compound 10 BD1 3.50 6.59 (0.135, 0.144) 52.8 Example 11 compound 11 BD1 3.49 6.55 (0.134, 0.140) 53.3 Example 12 compound 12 BD1 3.55 6.67 (0.134, 0.149) 55.1 Example 13 compound 13 BD1 3.38 6.71 (0.135, 0.147) 53.4 Example 14 compound 14 BD1 3.54 6.63 (0.134, 0.142) 53.8 Example 15 compound 15 BD1 3.40 6.57 (0.134, 0.145) 55.5 Example 16 compound 16 BD1 3.55 6.60 (0.134, 0.144) 54.9 Example 17 compound 17 BD1 3.56 6.62 (0.135, 0.138) 54.2 Example 18 compound 18 BD1 3.58 6.66 (0.134, 0.137) 58.4 Example 19 compound 19 BD1 3.60 6.67 (0.134, 0.137) 56.1 Example 20 compound 20 BD1 3.51 6.70 (0.134, 0.149) 58.1 Example 21 compound 21 BD1 3.53 6.59 (0.134, 0.140) 54.6 Example 22 compound 22 BD1 3.52 6.54 (0.134, 0.142) 59.0 Example 23 compound 23 BD1 3.40 6.58 (0.135, 0.148) 60.8 Example 24 compound 24 BD1 3.55 6.70 (0.134, 0.137) 55.4 Example 25 compound 25 BD1 3.39 6.60 (0.134, 0.138) 53.7 Example 26 compound 26 BD1 3.58 6.66 (0.134, 0.138) 57.8 Example 27 compound 27 BD1 3.42 6.58 (0.134, 0.138) 56.1 Example 28 compound 28 BD1 3.41 6.59 (0.135, 0.143) 54.0 Example 29 compound 29 BD1 3.50 6.64 (0.135, 0.149) 55.9 Example 30 compound 30 BD1 3.58 6.65 (0.134, 0.138) 56.7 Example 31 compound 31 BD1 3.52 6.64 (0.135, 0.138) 75.9 Example 32 compound 32 BD1 3.49 6.54 (0.134, 0.140) 71.8 Example 33 compound 33 BD1 3.54 6.60 (0.134, 0.140) 75.3 Example 34 compound 8 BD2 3.51 6.86 (0.134, 0.142) 50.3 Example 35 compound 19 BD2 3.72 6.90 (0.134, 0.137) 49.5 Example 36 compound 23 BD2 3.64 6.76 (0.135, 0.148) 53.4 Example 37 compound 29 BD2 3.69 6.81 (0.135, 0.149) 50.1 Example 38 compound 30 BD2 3.73 6.83 (0.134, 0.138) 48.3 Comparative Example 1 BH1 BD1 3.98 5.89 (0.134, 0.138) 35.1 Comparative Example 2 BH2 BD1 7.81 1.23 (0.145, 0.190) 1.5 Comparative Example 3 BH3 BD1 7.83 1.58 (0.151, 0.189) 3.4 Comparative Example 4 BH4 BD1 8.03 1.34 (0.148, 0.191) 3.5 Comparative Example 5 BH5 BD1 3.90 5.91 (0.134, 0.138) 36.8 Comparative Example 6 BH6 BD1 6.23 2.58 (0.134, 0.143) 15.8 Comparative Example 7 BH7 BD1 6.12 2.54 (0.134, 0.140) 5.1 Comparative Example 8 BH8 BD1 5.98 5.05 (0.134, 0.139) 10.2 Comparative Example 9 BH9 BD1 4.83 5.78 (0.134, 0.138) 14.1 Comparative Example 10 BH10 BD1 3.99 5.80 (0.134, 0.138) 15.3 Comparative Example 11 BH5 BD2 4.08 6.02 (0.134, 0.138) 23.1 Comparative Example 12 BH10 BD2 4.12 5.98 (0.134, 0.138) 12.4

The present specification is an anthracene blue fluorescent host in which an oxazole-condensed unit and dibenzofuran are introduced into an aryl series, and an improvement of a blue light-emitting device is achieved by improving hole and electron injection, transport, and control characteristics. By showing the various derivatives known in the prior art in Comparative Examples 1 to 12, it is possible to observe a significant improvement in device performance of the blue device compared to the prior art.

BH2 to BH4 used in Comparative Examples 2 to 4 have a structure in which azine series and anthracene are introduced, but Ar of Formula 1 of the present application is not introduced. Specifically, it can be seen that the color coordinates of BH2 to BH4 used in Comparative Examples 2 to 4 are different from the color coordinate range of Examples, and the device performance of Comparative Examples 2 to 4 is also significantly lower than in Examples. This is a result that appears because the energy levels of the band gap, HOMO, LUMO, etc. of BH2 to BH4 used in Comparative Examples 2 to 4 are not suitable for use as a blue host.

BH6 used in Comparative Example 6 had a low bandgap as a blue host in its structure, and thus did not properly show its role as a light emitting layer.

The organic electroluminescent device using the compound of Formula 1 according to the present specification can control the role of smooth hole injection into the light emitting layer by using the compounds of Preparation Examples 5 and 6 as a host of the blue organic electroluminescent device, and according to the chemical structure Through the balance of holes and electrons of the organic light emitting device, the device according to the present specification exhibits superior characteristics in terms of efficiency, driving voltage, and stability compared to Comparative Examples.

In addition, it can be confirmed that Example 1 using Compound 1 has a lower driving voltage, higher efficiency, and longer life than Comparative Example 5 using BH5 in which A1 is hydrogen.

1: substrate
2: first electrode
2-1: Anode
3: organic layer
4: second electrode
4-1: cathode
5: first organic layer
6: light emitting layer
7: second organic layer
8: hole injection layer
9: hole transport layer
10: electronic control layer
11: electron transport layer
12: electron injection layer
13: capping layer

Claims (17)

A compound of formula (1):
[Formula 1]

In Formula 1,
X is O or S;
R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; nitro group; hydroxyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
r is an integer from 1 to 4, r1 is an integer from 1 to 8, r2 is an integer from 1 to 6,
When r is 2 or more, Ar is the same as or different from each other,
When r1 is 2 or more, R1 is the same as or different from each other,
When r2 is 2 or more, R2 are the same as or different from each other,
L1 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,
L2 is a direct bond, a substituted or unsubstituted r+1 valent aryl group, or a substituted or unsubstituted r+1 valent heterocyclic group,
Ar is a substituent of formula A,
[Formula A]

In the above formula (A),
Y is O or S;
A1 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; nitro group; hydroxyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
a1 is an integer from 1 to 7,
When a1 is 2 or more, A1 is the same as or different from each other,
* is a position bonded to Formula 1,
when L1 is a direct bond, L2 is a substituted or unsubstituted r+1 valent aryl group, or a substituted or unsubstituted r+1 valent heterocyclic group; A1 is a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. The method according to claim 1, wherein Formula 1 is a compound of Formula 2 or 3 below:
[Formula 2]

[Formula 3]

In Formulas 2 and 3, R1, R2, Ar, r, r1, r2, L1 and L2 are the same as defined in Formula 1. The method according to claim 1, wherein Formula 1 is a compound of Formula 2-1, 2-2, 3-1, or 3-2 below:
[Formula 2-1]

[Formula 2-2]

[Formula 3-1]

[Formula 3-2]

In Formulas 2-1, 2-2, 3-1, and 3-2, R1, R2, Ar, r, r1, r2, L1, and L2 have the same definitions as in Formula 1. The method according to claim 1, wherein Chemical Formula 1 is the following Chemical Formulas 2-1-1, 2-1-2, 2-1-3, 2-2-1, 2-2-2, 2-2-3, 3-1 -1, 3-1-2, 3-1-3, 3-2-1, 3-2-2 or 3-2-3
[Formula 2-1-1]

[Formula 2-1-2]

[Formula 2-1-3]

[Formula 2-2-1]

[Formula 2-2-2]

[Formula 2-2-3]

[Formula 3-1-1]

[Formula 3-1-2]

[Formula 3-1-3]

[Formula 3-2-1]

[Formula 3-2-2]

[Formula 3-2-3]

Formula 2-1-1, 2-1-2, 2-1-3, 2-2-1, 2-2-2, 2-2-3, 3-1-1, 3-1-2, In 3-1-3, 3-2-1, 3-2-2 and 3-2-3, R1, R2, Ar, r, r1, r2, L1 and L2 are as defined in Formula 1,
R3 and R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; nitro group; hydroxyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
r4 is an integer from 1 to 5,
When r4 is 2 or more, R4 is the same as or different from each other. The compound according to claim 1, wherein Formula 1 is any one of Formulas 4 to 24:
[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

[Formula 22]

[Formula 23]

[Formula 24]

In Formulas 4 to 24, X, R1, R2, Ar, r, r1, r2, L1 and L2 are the same as defined in Formula 1,
R3 and R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; nitro group; hydroxyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
r4 is an integer from 1 to 5,
When r4 is 2 or more, R4 is the same as or different from each other. The compound according to claim 1, wherein the bandgap energy of the compound is 2.9 eV or more. The compound according to claim 1, wherein the compound has a deuterium substitution rate of 1% to 100%. The compound according to claim 1, wherein the compound has a deuterium substitution rate of 40% to 99%. The compound according to claim 1, wherein the compound of Formula 1 has any one of the following structures:

. a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode,
At least one of the organic material layers is an organic light emitting device comprising the compound according to any one of claims 1 to 9. The organic light emitting device of claim 10 , wherein the organic material layer includes a light emitting layer including a host and a dopant, and the host includes at least one compound. The method according to claim 11, wherein the host comprises a first anthracene derivative substituted with deuterium and a second anthracene derivative unsubstituted with deuterium, and any one of the first anthracene derivative and the second anthracene derivative comprises the compound. phosphorus organic light emitting device. The organic light-emitting device of claim 12 , wherein the first anthracene derivative substituted with deuterium includes the compound. The organic light-emitting device of claim 11 , wherein the dopant is a fluorescent dopant. The organic light-emitting device of claim 11 , wherein the dopant includes a pyrene-based compound or a non-pyrene-based compound. The organic light-emitting device of claim 15 , wherein the non-pyrene-based compound includes a boron-based compound. The organic light emitting diode of claim 11 , wherein the maximum emission peak (λ _max ) of the emission layer including the compound is in the range of 400 nm to 470 nm.

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