KR20210131639A - Heterocyclic compound and organic light emitting device comprising same - Google Patents

Abstract

The present specification relates to a heterocyclic compound represented by chemical formula 1 and an organic light emitting device including the same. A compound according to an exemplary embodiment of the present specification can be used in an organic light emitting device to lower the driving voltage and improve light efficiency of the organic light emitting device. In addition, lifespan characteristics of a device can be improved by the thermal stability of the compound.

Description

Heterocyclic compound and organic light emitting device comprising same {HETEROCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME}

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

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

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

Laid-Open Patent Publication No. 10-2013-0135162

An object of the present specification is to provide a heterocyclic compound and an organic light emitting device including the same.

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

[Formula 1]

In Formula 1,

At least 2 or more of X1 to X3 are N, the rest are CH,

L1 to L4 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,

Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

n1 to n4 are integers from 0 to 4,

m1 is an integer from 0 to 4,

When n1 to n4 and m1 are each 2 or more, the substituents in parentheses are the same or different from each other,

A1 is represented by the following formula 1-1 or 1-2,

[Formula 1-1] [Formula 1-2]

In Formula 1-1,

Any one of Cy1 and Cy2 is a naphthalene ring, and the other is a benzene ring,

G1 is a direct bond or -C(R17)(R18)-; -O-; or -S-;

any one of R11 to R14 is connected to L1 of Formula 1, the other is connected to L4 of Formula 1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R17 and R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r11 and r13 are integers from 0 to 4,

any one of r12 and r14 is an integer from 0 to 6, the other is an integer from 0 to 4,

When each of r11 to r14 is 2 or more, the substituents in parentheses are the same or different from each other,

In Formula 1-2,

Cy3 is a naphthalene ring,

Ar4 and Ar5 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

any one of R15 and R16 is connected to L1 of Formula 1, the other is connected to L4 of Formula 1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r15 is an integer from 0 to 4,

r16 is an integer from 0 to 6,

When r15 and r16 are each 2 or more, the substituents in parentheses are the same as or different from each other.

In addition, the present specification is a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one organic material layer includes the heterocyclic compound represented by Formula 1 above. provides

The compound according to an exemplary embodiment of the present specification may be used in an organic light emitting device, may lower the driving voltage of the organic light emitting device, and may improve light efficiency. In addition, the lifespan characteristics of the device can be improved by the thermal stability of the compound.

1 and 2 show an example of an organic light emitting device according to an exemplary embodiment of the present specification.

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

Since the compound represented by Formula 1 includes a polycyclic cyclic group represented by A and pyridine having an electron depletion structure, the dipole moment of the molecule can be increased. By smoothly controlling it, the efficiency and lifespan of the organic light emitting diode can be improved, and the driving voltage can be lowered.

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

은 연결되는 부위를 의미한다.In this specification,

denotes a part to be connected.

In the present specification, Cn means n carbon atoms.

In the present specification, “Cn-Cm” means “n to m carbon atoms”.

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; an alkyl group; aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a heteroaryl group containing one or more heteroatoms other than carbon, or is substituted with a substituent to which two or more substituents of the above exemplified substituents are linked, or does not have any substituents means that

또는

의 치환기가 될 수 있다. In the present specification, that two or more substituents are connected means that the hydrogen of any one substituent is connected with another substituent. For example, 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 three substituents are connected not only to (substituent 1)-(substituent 2)-(substituent 3) being continuously connected, but also (substituent 1) to (substituent 2) and (substituent 3) 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, examples of the halogen group include fluorine, chlorine, bromine, or iodine.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but 1 to 30; 1 to 20; 1 to 10; Or 1 to 6 are preferable. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, iso Pentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentyl Methyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1 -Dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the aryl group means a monovalent group of a monovalent aromatic hydrocarbon or an aromatic hydrocarbon derivative. In the present specification, the aromatic hydrocarbon refers to a compound in which the pi electrons are completely conjugated and includes a planar ring, and the group derived from the aromatic hydrocarbon refers to a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is condensed with an aromatic hydrocarbon. . Also, in the present specification, the aryl group is intended to include a monovalent group in which two or more aromatic hydrocarbons or derivatives of aromatic hydrocarbons are connected to each other. The aryl group is not particularly limited, but has 6 to 50 carbon atoms; 6 to 30; 6 to 25; 6 to 20; 6 to 18; Or it is preferably 6 to 13, and the aryl group may be monocyclic or polycyclic. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

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

In the present specification, when it is said that the fluorenyl group may be substituted, the substituted fluorenyl group includes all compounds in which the substituents of the pentacyclic ring of fluorene are spiro-bonded with each other to form an aromatic hydrocarbon ring. The substituted fluorenyl group includes 9,9'-spirobifluorene, spiro[cyclopentane-1,9'-fluorene], spiro[benzo[c]fluorene-7,9-fluorene], etc. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group includes atoms other than carbon and one or more heteroatoms, and specifically, the heterocyclic group may include one or more atoms selected from the group consisting of O, N, Si and S. Although the number of carbon atoms is not particularly limited, 2 to 50 carbon atoms; 2 to 30; 2 to 20; 2 to 18; Or it is preferable that it is 2-13. Examples of the heterocyclic group include a thiophene group, a furanyl group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridine group. , pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyridopyrimidine group, pyridopyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benzoxa Zol group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthroline group, thiazole group, isoxazole group, oxadiazole group, thia diazole group, benzothiazole group, phenothiazine group, dibenzofuran group, dihydrophenothiazine group, dihydrobenzoisoquinoline group, chromene group, and the like, but is not limited thereto.

In the present specification, the heterocyclic group may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of an aromatic and aliphatic group, and may be selected from examples of the heterocyclic group.

In the present specification, the heteroaryl group refers to a monovalent aromatic heterocycle. Here, the aromatic heterocycle is a monovalent group of an aromatic ring or a derivative of an aromatic ring, and means a group including at least one of O, N, Si and S as heteroatoms in the ring. The derivative of the aromatic ring includes all structures in which an aromatic ring or an aliphatic ring is condensed on an aromatic ring. Also, in the present specification, the heteroaryl group is intended to include a monovalent group in which an aromatic ring containing two or more heteroatoms or a derivative of an aromatic ring containing heteroatoms is connected to each other. the heteroaryl group having 2 to 50 carbon atoms; 2 to 30; 2 to 20; 2 to 18; Or it is preferable that it is 2-13.

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

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

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

[Formula 1]

In an exemplary embodiment of the present specification, at least two or more of X1 to X3 are N, and the rest are CH.

In an exemplary embodiment of the present specification, X1 and X2 are N, and X3 is CH.

In an exemplary embodiment of the present specification, X1 and X3 are N, and X2 is CH.

In an exemplary embodiment of the present specification, X2 and X3 are N, and X2 is CH.

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

In an exemplary embodiment of the present specification, L1 to L4 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 L4 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group.

In an exemplary embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted C6-C60 arylene group.

In an exemplary embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted C6-C30 arylene group.

In an exemplary embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a direct bond; or a C6-C30 arylene group.

In an exemplary embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a direct bond; or a C6-C20 arylene group.

In an exemplary embodiment of the present specification, L1 to L4 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; or a substituted or unsubstituted naphthylene group.

In an exemplary embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a direct bond; phenylene group; or a biphenylene group.

In one embodiment of the present specification, at least one of L1 and L4 is a direct bond.

In an exemplary embodiment of the present specification, one of L1 and L4 is a direct bond, and the other is a substituted or unsubstituted arylene group,

In an exemplary embodiment of the present specification, one of L1 and L4 is a direct bond, and the other is a substituted or unsubstituted phenylene group,

In one embodiment of the present specification, L1 is a direct bond.

In one embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted C6-C20 arylene group.

In one embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.

In one embodiment of the present specification, L1 to L4 are the same as or different from each other, and are each independently selected from a direct bond or the following structure.

In one embodiment of the present specification, n1 to n4 are integers from 0 to 4.

When n1 is 2 or more, a plurality of L1s are the same as or different from each other. When n2 is 2 or more, a plurality of L2s are the same as or different from each other. When n3 is 2 or more, a plurality of L3s are the same as or different from each other. When n4 is 2 or more, a plurality of L4s are the same as or different from each other.

In an exemplary embodiment of the present specification, n1 to n4 are integers of 0 to 2.

In one embodiment of the present specification, n1 + n4 is 1 or more.

In one embodiment of the present specification, n1 + n4 is 1 or 2.

In the exemplary embodiment of the present specification, n2 and n3 are 0.

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

In an exemplary embodiment of the present specification, Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C6-C60 aryl group; Or a substituted or unsubstituted C2-C60 heteroaryl group.

In an exemplary embodiment of the present specification, Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

In an exemplary embodiment of the present specification, Ar1 to Ar3 are the same as or different from each other, and each independently a C1-C10 alkyl group; a C6-C30 aryl group unsubstituted or substituted with a C1-C10 alkyl group or a C2-C30 heteroaryl group; or a C2-C30 heteroaryl group.

In an exemplary embodiment of the present specification, Ar1 to Ar3 are the same as or different from each other, and each independently a C1-C6 alkyl group; a C6-C20 aryl group unsubstituted or substituted with a C1-C6 alkyl group or a C2-C20 heteroaryl group; or a C2-C20 heteroaryl 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 C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl 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 C1-C6 alkyl group; a C6-C20 aryl group unsubstituted or substituted with a C1-C6 alkyl group or a C2-C20 heteroaryl group; or a C2-C20 heteroaryl group.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; A substituted or unsubstituted C2-C30 heteroaryl group.

In an exemplary embodiment of the present specification, Ar3 is a C1-C6 alkyl group; C6-C20 aryl group; or a C2-C20 heteroaryl group.

In an exemplary embodiment of the present specification, Ar3 is a C1-C6 alkyl group; or a C6-C20 aryl group.

In an exemplary embodiment of the present specification, at least one of the plurality of Ar3 is a substituted or unsubstituted C1-C10 alkyl group.

In an exemplary embodiment of the present specification, at least one of the plurality of Ar3 is a substituted or unsubstituted C1-C6 alkyl group.

In an exemplary embodiment of the present specification, one or two of the plurality of Ar3 is a substituted or unsubstituted C1-C10 alkyl group.

In the exemplary embodiment of the present specification, the heteroaryl group of Ar1 to Ar3 includes N, O or S as a heteroatom.

In an exemplary embodiment of the present specification, Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted isopropyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted tert-butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted naphthobenzofuran group; Or a substituted or unsubstituted naphthobenzothiophene 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 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 naphthyl group; a substituted or unsubstituted pyridyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene 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 methyl group; a phenyl group unsubstituted or substituted with a methyl group or a pyridyl group; biphenyl group; naphthyl group; dibenzofuran group; or a dibenzothiophene group.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted isopropyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted tert-butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted naphthobenzofuran group; Or a substituted or unsubstituted naphthobenzothiophene group.

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

In an exemplary embodiment of the present specification, Ar3 is a methyl group; or a phenyl group.

In an exemplary embodiment of the present specification, at least one of a plurality of Ar3 is a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted isopropyl group; a substituted or unsubstituted butyl group; or a substituted or unsubstituted tert-butyl group.

In the exemplary embodiment of the present specification, m1 is an integer of 0 to 4, and when 2 or more, a plurality of Ar3 are the same or different from each other.

In one embodiment of the present specification, m1 is an integer of 0 to 3.

In one embodiment of the present specification, m1 is an integer of 0 to 2.

In an exemplary embodiment of the present specification, m1 is 0.

In one embodiment of the present specification, m1 is 1 or 2.

In an exemplary embodiment of the present specification, A1 is represented by the following Chemical Formula 1-1 or 1-2.

[Formula 1-1] [Formula 1-2]

In Formula 1-1,

Any one of Cy1 and Cy2 is a naphthalene ring, and the other is a benzene ring,

G1 is a direct bond or -C(R17)(R18)-; -O-; or -S-;

any one of R11 to R14 is connected to L1 of Formula 1, the other is connected to L4 of Formula 1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R17 and R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r11 and r13 are integers from 0 to 4,

any one of r12 and r14 is an integer from 0 to 6, the other is an integer from 0 to 4,

When each of r11 to r14 is 2 or more, the substituents in parentheses are the same or different from each other,

In Formula 1-2,

Cy3 is a naphthalene ring,

Ar4 and Ar5 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

any one of R15 and R16 is connected to L1 of Formula 1, the other is connected to L4 of Formula 1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r15 is an integer from 0 to 4,

r16 is an integer from 0 to 6,

When r15 and r16 are each 2 or more, the substituents in parentheses are the same as or different from each other.

In an exemplary embodiment of the present specification, Cy1 is a benzene ring, and Cy2 is a naphthalene ring.

In an exemplary embodiment of the present specification, Cy1 is a naphthalene ring, and Cy2 is a benzene ring.

In one embodiment of the present specification, G1 is a direct bond, or -O-; or -S-.

In the exemplary embodiment of the present specification, the remainder not connected to the formulas L1 and L4 among R11 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

In the exemplary embodiment of the present specification, the remainder not connected to the formulas L1 and L4 among R11 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; C1-C6 alkyl group; or a C6-C20 aryl group.

In the exemplary embodiment of the present specification, the remainder not connected to the formulas L1 and L4 among R11 to R14 are the same as or different from each other, and each independently hydrogen; or deuterium.

In the exemplary embodiment of the present specification, the remainder not connected to the formulas L1 and L4 among R11 to R14 is hydrogen.

In the exemplary embodiment of the present specification, the remainder not connected to the formulas L1 and L4 among R15 and R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

In the exemplary embodiment of the present specification, the remainder not connected to the formulas L1 and L4 among R15 and R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; C1-C6 alkyl group; or a C6-C20 aryl group.

In the exemplary embodiment of the present specification, the remainder not connected to the formulas L1 and L4 among R15 and R16 are the same as or different from each other, and each independently hydrogen; or deuterium.

In the exemplary embodiment of the present specification, the remainder not connected to the formulas L1 and L4 among R15 and R16 is hydrogen.

In an exemplary embodiment of the present specification, R17 and R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

In an exemplary embodiment of the present specification, R17 and R18 are the same as or different from each other, and each independently represents a C1-C10 alkyl group.

In an exemplary embodiment of the present specification, R17 and R18 are methyl groups.

In an exemplary embodiment of the present specification, Formula 1-1 is represented by Formula A11 or A12, and Formula 1-2 is represented by Formula A21.

[Formula A11] [Formula A12]

[Formula A21]

In the formulas A11 and A12,

The definition of G1 is as defined in Formula 1-1,

any one of R21 to R38 is connected to L1 of Formula 1, the other is connected to L4 of Formula 1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

In the formula A21,

Ar4 and Ar5 are the same as defined in Formula 1-2,

any one of R41 to R50 is connected to L1 of Formula 1, the other is connected to L4 of Formula 1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, R21 is connected to L1 of Formula 1 above. In another exemplary embodiment, R22 is connected to L1 in Formula 1 above. In another exemplary embodiment, R23 is connected to L1 of Formula 1 above. In another exemplary embodiment, R24 is connected to L1 in Formula 1 above. In another exemplary embodiment, R25 is connected to L1 of Formula 1 above. In another exemplary embodiment, R26 is connected to L1 of Formula 1 above. In another exemplary embodiment, R27 is connected to L1 of Formula 1 above. In another exemplary embodiment, R28 is connected to L1 of Formula 1 above. In another exemplary embodiment, R29 is connected to L1 of Formula 1 above. In another exemplary embodiment, R30 is connected to L1 of Formula 1 above. In another exemplary embodiment, R31 is connected to L1 of Formula 1 above. In another exemplary embodiment, R32 is connected to L1 in Formula 1 above. In another exemplary embodiment, R33 is connected to L1 in Formula 1 above. In another exemplary embodiment, R34 is connected to L1 in Formula 1 above. In another exemplary embodiment, R35 is connected to L1 of Formula 1 above. In another exemplary embodiment, R36 is connected to L1 of Formula 1 above. In another exemplary embodiment, R37 is connected to L1 in Formula 1 above. In another exemplary embodiment, R38 is connected to L1 of Formula 1 above.

In the exemplary embodiment of the present specification, R21 is connected to L4 of Formula 1 above. In another exemplary embodiment, R22 is connected to L4 in Formula 1 above. In another exemplary embodiment, R23 is connected to L4 in Formula 1 above. In another exemplary embodiment, R24 is connected to L4 in Formula 1 above. In another exemplary embodiment, R25 is connected to L4 in Formula 1 above. In another exemplary embodiment, R26 is connected to L4 in Formula 1 above. In another exemplary embodiment, R27 is connected to L4 of Formula 1 above. In another exemplary embodiment, R28 is connected to L4 in Formula 1 above. In another exemplary embodiment, R29 is connected to L4 in Formula 1 above. In another exemplary embodiment, R30 is connected to L4 of Formula 1 above. In another exemplary embodiment, R31 is connected to L4 in Formula 1 above. In another exemplary embodiment, R32 is connected to L4 in Formula 1 above. In another exemplary embodiment, R33 is connected to L4 in Formula 1 above. In another exemplary embodiment, R34 is connected to L4 in Formula 1 above. In another exemplary embodiment, R35 is connected to L4 in Formula 1 above. In another exemplary embodiment, R36 is connected to L4 in Formula 1 above. In another exemplary embodiment, R37 is connected to L4 in Formula 1 above. In another exemplary embodiment, R38 is connected to L4 in Formula 1 above.

In an exemplary embodiment of the present specification, R41 is connected to L1 of Formula 1 above. In another exemplary embodiment, R42 is connected to L1 of Formula 1 above. In another exemplary embodiment, R43 is connected to L1 of Formula 1 above. In another exemplary embodiment, R44 is connected to L1 in Formula 1 above. In another exemplary embodiment, R45 is connected to L1 of Formula 1 above. In another exemplary embodiment, R46 is connected to L1 of Formula 1 above. In another exemplary embodiment, R47 is connected to L1 of Formula 1 above. In another exemplary embodiment, R48 is connected to L1 of Formula 1 above. In another exemplary embodiment, R49 is connected to L1 in Formula 1 above. In another exemplary embodiment, R50 is connected to L1 of Formula 1 above.

In the exemplary embodiment of the present specification, R41 is connected to L4 of Formula 1 above. In another exemplary embodiment, R42 is connected to L4 in Formula 1 above. In another exemplary embodiment, R43 is connected to L4 in Formula 1 above. In another exemplary embodiment, R44 is connected to L4 in Formula 1 above. In another exemplary embodiment, R45 is connected to L4 in Formula 1 above. In another exemplary embodiment, R46 is connected to L4 in Formula 1 above. In another exemplary embodiment, R47 is connected to L4 of Formula 1 above. In another exemplary embodiment, R48 is connected to L4 in Formula 1 above. In another exemplary embodiment, R49 is connected to L4 of Formula 1 above. In another exemplary embodiment, R50 is connected to L4 in Formula 1 above.

In an exemplary embodiment of the present specification, Ar4 and Ar5 are the same as or different from each other, and each independently a substituted or unsubstituted C1-C20 alkyl group; or a substituted or unsubstituted C6-C60 aryl group.

In an exemplary embodiment of the present specification, Ar4 and Ar5 are the same as or different from each other, and each independently a substituted or unsubstituted C1-C10 alkyl group; or a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, Ar4 and Ar5 are the same as or different from each other, and each independently a C1-C10 alkyl group; or a C6-C30 aryl group.

In an exemplary embodiment of the present specification, Ar4 and Ar5 are the same as or different from each other, and each independently a C1-C6 alkyl group; or a C6-C20 aryl group.

In an exemplary embodiment of the present specification, Ar4 and Ar5 are the same as or different from each other, and each independently a substituted or unsubstituted methyl group; or a substituted or unsubstituted phenyl group.

In an exemplary embodiment of the present specification, Ar4 and Ar5 are the same as or different from each other, and each independently a methyl group; or a phenyl group.

In an exemplary embodiment of the present specification, Ar4 and Ar5 are the same as each other.

In an exemplary embodiment of the present specification, any one of R21 to R38 is connected to L1 of Formula 1, the other is connected to L4 of Formula 1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

In the exemplary embodiment of the present specification, among R21 to R38, the remainder not connected to the formulas L1 and L4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; C1-C6 alkyl group; or a C6-C20 aryl group.

In the exemplary embodiment of the present specification, among R21 to R38, the remainder not connected to the formulas L1 and L4 are the same as or different from each other, and each independently hydrogen; or deuterium.

In the exemplary embodiment of the present specification, the remainder not connected to Formulas L1 and L4 among R21 to R38 is hydrogen.

In an exemplary embodiment of the present specification, any one of R41 to R50 is connected to L1 of Formula 1, the other is connected to L4 of Formula 1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

In the exemplary embodiment of the present specification, the remainder not connected to the formulas L1 and L4 among R41 to R50 are the same or different from each other, and each independently hydrogen; heavy hydrogen; C1-C6 alkyl group; or a C6-C20 aryl group.

In the exemplary embodiment of the present specification, the remainder not connected to the formulas L1 and L4 among R41 to R50 are the same or different from each other, and each independently hydrogen; or deuterium.

In the exemplary embodiment of the present specification, the remainder not connected to Formulas L1 and L4 among R41 to R50 is hydrogen.

In the exemplary embodiment of the present specification, Chemical Formula 1-1 is represented by any one of Chemical Formulas A13 to A18 below.

[Formula A13] [Formula A14]

[Formula A15] [Formula A16]

[Formula A17] [Formula A18]

In the formulas A13 to A18,

The definition of G1 is as defined in Formula 1-1,

any one of R21 to R38 is connected to L1 of Formula 1, the other is connected to L4 of Formula 1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, Formula A11 is represented by any one of Formulas A13 to A15.

In an exemplary embodiment of the present specification, Formula A12 is represented by any one of Formulas A16 to A18.

In an exemplary embodiment of the present specification, Formula 1-2 is represented by any one of Formulas A22 to A24 below.

[Formula A22] [Formula A23]

[Formula A24]

In the formulas A22 to A24,

Ar4 and Ar5 are the same as defined in Formula 1-2,

any one of R41 to R50 is connected to L1 of Formula 1, the other is connected to L4 of Formula 1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, A1 is a divalent group selected from the following groups 1 to 9.

[Group 1]

[Group 2]

[Group 3]

[Group 4]

[Group 5]

[Group 6]

[Group 7]

[Group 8]

[Group 9]

In groups 1 to 9,

G1 is a direct bond or -C(R17)(R18)-; -O-; or -S-;

Ar4 and Ar5 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

The structure is deuterium; cyano group; an alkyl group; aryl group; Or substituted or unsubstituted with a heteroaryl group,

는 화학식 1의 L1 또는 L4에 연결되는 위치이다.

is a position connected to L1 or L4 of Formula 1;

In one embodiment of the present specification, the structure of A1 is deuterium; cyano group; C1-C10 alkyl group; C6-C30 aryl group; Or it is unsubstituted or substituted with a C2-C30 heteroaryl group.

In the exemplary embodiment of the present specification, the structure of A1 does not have any substituents.

In an exemplary embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a direct bond; Or a C6-C30 arylene group,

Ar1 to Ar3 are the same as or different from each other, and each independently a C1-C10 alkyl group; a C6-C30 aryl group unsubstituted or substituted with a C1-C10 alkyl group or a C2-C30 heteroaryl group; Or a C2-C30 heteroaryl group,

of R11 to R14, the remainder not connected to Formulas L1 and L4 may be the same as or different from each other, and each independently hydrogen; or deuterium,

R17 and R18 are the same as or different from each other, and each independently represents a C1-C10 alkyl group,

Ar4 and Ar5 are the same as or different from each other, and each independently a C1-C10 alkyl group; Or a C6-C30 aryl group,

R15 and R16, the remainder not connected to Formulas L1 and L4 are the same as or different from each other, and each independently hydrogen; or deuterium.

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

The compound according to an exemplary embodiment of the present specification may be prepared by a manufacturing 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, and the like can be changed. The manufacturing method may be more specific in Preparation Examples to be described later.

The present specification provides an organic light emitting device including the above-described compound.

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

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

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

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

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

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

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

In the exemplary embodiment of the present specification, the electron injection layer, the electron transport layer, the electron injection and transport layer, or the hole blocking layer further include an n-type dopant.

The n-type dopant may be one or two or more selected from alkali metals and alkaline earth metals.

When the organic alkali metal compound or the organic alkaline earth metal compound is used as the n-type dopant, it is possible to secure stability to holes from the light emitting layer, thereby improving the lifespan of the organic light emitting device. In addition, by adjusting the ratio of the organic alkali metal compound or the organic alkaline earth metal compound to the electron mobility of the electron transport layer, it is possible to maximize the balance of holes and electrons in the light emitting layer, thereby increasing luminous efficiency.

LiQ is more preferable as the n-type dopant used in the electron transport layer in the present specification.

The electron transport layer may include the heterocyclic compound represented by Formula 1 and the n-type dopant in a weight ratio of 1:9 to 9:1. Preferably, the heterocyclic compound of Formula 1 and the n-type dopant may be included in an amount of 2:8 to 8:2, more preferably 3:7 to 7:3.

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

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

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

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

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

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

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

For example, the structure of the organic light emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 to 2 . 1 and 2 illustrate an organic light emitting device, but is not limited thereto.

1 illustrates a structure of an organic light emitting device in which an anode 102, a light emitting layer 106, and a cathode 108 are sequentially stacked on a substrate 101. As shown in FIG. The compound represented by Formula 1 is included in the light emitting layer.

2 shows an anode 102, a hole injection layer 103, a first hole transport layer 104, a second hole transport layer 105, a light emitting layer 106, an electron injection and transport layer 107, and a cathode on a substrate 101. The structure of the organic light emitting device in which 108 is sequentially stacked is illustrated. According to an exemplary embodiment of the present specification, the compound represented by Formula 1 is included in the electron injection and transport layer 107 .

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

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

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

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

As the anode material, a material having a large work function is generally preferable to facilitate hole injection into the organic material layer. For example, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO ₂ : a combination of a metal such as Sb and an oxide; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

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

The emission layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a compound containing a hetero ring. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but is not limited thereto.

In an exemplary embodiment of the present specification, an anthracene derivative substituted with deuterium may be used as a host material of the light emitting layer.

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

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

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

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

The electron injection layer is a layer that receives electrons from the electrode. It is preferable that the electron injecting material is excellent in the ability to transport electrons and has an electron receiving effect from the cathode and an excellent electron injecting effect with respect to the light emitting layer or the light emitting material. In addition, a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. derivatives thereof; metal complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

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

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

The hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the electron injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, and the like, but is not limited thereto.

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

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

[Synthesis Example]

Synthesis Example 1

The compound 1-1 (13.3 g, 30 mmol) and the compound 1-2 (8.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(dba) ₂ (0.6 g), and PCy ₃ (0.6 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from chloroform and ethanol by filtration to prepare Compound 1-3. (13.7 g, yield 72%, MS:[M+H]+=633).

The compound 1-3 (19.0 g, 30 mmol) and the compound 1-4 (4.1 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(PtBu ₃ ) ₂ (0.9 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 1. (10.5 g, yield 52%, MS:[M+H]+=675).

Synthesis Example 2

The compound 2-1 (14.6 g, 30 mmol) and the compound 2-2 (10.5 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(dba) ₂ (0.6 g), and PCy ₃ (0.6 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from chloroform and ethanol by filtration to prepare Compound 2-3. (16.3 g, yield 75%, MS:[M+H]+= 724).

The compound 2-3 (21.7 g, 30 mmol) and the compound 2-4 (4.1 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(PtBu ₃ ) ₂ (0.9 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 2 above. (9.9 g, yield 43%, MS:[M+H]+=767).

Synthesis Example 3

The compound 3-1 (14.3 g, 30 mmol) and the compound 3-2 (10.5 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(dba) ₂ (0.6 g), and PCy ₃ (0.6 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from chloroform and ethanol by filtration to prepare Compound 3-3. (17.1 g, yield 80%, MS:[M+H]+= 714).

The compound 3-3 (21.4 g, 30 mmol) and the compound 3-4 (4.1 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(PtBu ₃ ) ₂ (0.9 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 3 above. (9.5 g, yield 42%, MS:[M+H]+=756).

Synthesis Example 4

The compound 4-1 (13.3 g, 30 mmol) and the compound 4-2 (4.7 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(dba) ₂ (0.6 g), and PCy ₃ (0.6 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from chloroform and ethanol by filtration to prepare Compound 4-3. (9.9 g, yield 65%, MS:[M+H]+=509).

The compound 4-3 (15.2 g, 30 mmol) and the compound 4-4 (4.5 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(PtBu ₃ ) ₂ (0.9 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 4 above. (10.0 g, yield 59%, MS: [M+H] + = 565).

Synthesis Example 5

The compound 5-1 (14.6 g, 30 mmol) and the compound 5-2 (8.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(dba) ₂ (0.6 g), and PCy ₃ (0.6 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from chloroform and ethanol by filtration to prepare Compound 5-3. (15.6 g, yield 77%, MS:[M+H]+=675).

The compound 5-3 (20.2 g, 30 mmol) and the compound 5-4 (5.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(PtBu ₃ ) ₂ (0.9 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 5. (13.4 g, yield 60%, MS:[M+H]+= 745).

Synthesis Example 6

The compound 6-1 (14.0 g, 30 mmol) and the compound 6-2 (8.9 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(dba) ₂ (0.6 g), and PCy ₃ (0.6 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from chloroform and ethanol by filtration to prepare Compound 6-3. (17.0 g, yield 85%, MS:[M+H]+=666).

The compound 6-3 (20.0 g, 30 mmol) and the compound 6-4 (6.6 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(PtBu ₃ ) ₂ (0.9 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 6 above. (16.7 g, yield 71%, MS:[M+H]+=785).

Synthesis Example 7

The compound 7-1 (13.3 g, 30 mmol) and the compound 7-2 (11.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(dba) ₂ (0.6 g), and PCy ₃ (0.6 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from chloroform and ethanol by filtration to prepare Compound 7-3. (17.2 g, yield 81%, MS:[M+H]+=709).

The compound 7-3 (21.2 g, 30 mmol) and the compound 7-4 (7.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(PtBu ₃ ) ₂ (0.9 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 7 above. (18.2 g, yield 72%, MS:[M+H]+=842).

Synthesis Example 8

The compound 8-1 (14.6 g, 30 mmol) and the compound 8-2 (8.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(dba) ₂ (0.6 g), and PCy ₃ (0.6 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from chloroform and ethanol by filtration to prepare Compound 8-3. (16.6 g, yield 82%, MS:[M+H]+=674).

The compound 8-3 (20.2 g, 30 mmol) and the compound 8-4 (4.1 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(PtBu ₃ ) ₂ (0.9 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 8. (11.2 g, yield 52%, MS: [M+H] + = 716).

Synthesis Example 9

The compound 9-1 (14.3 g, 30 mmol) and the compound 9-2 (10.5 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(dba) ₂ (0.6 g), and PCy ₃ (0.6 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from chloroform and ethanol by filtration to prepare compound 9-3. (13.3 g, yield 62%, MS:[M+H]+= 714).

The compound 9-3 (21.4 g, 30 mmol) and the compound 9-4 (4.1 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(PtBu ₃ ) ₂ (0.9 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized twice with ethyl acetate by filtration to prepare compound 9. (9.8 g, yield 43%, MS:[M+H]+=756).

Synthesis Example 10

The compound 10-1 (13.8 g, 30 mmol) and the compound 10-2 (6.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(dba) ₂ (0.6 g), and PCy ₃ (0.6 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from chloroform and ethanol by filtration to prepare Compound 10-3. (8.8 g, yield 50%, MS:[M+H]+=587).

The compound 10-3 (17.6 g, 30 mmol) and the compound 10-4 (4.1 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(PtBu ₃ ) ₂ (0.9 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 10. (12.3 g, yield 65%, MS: [M+H] + = 629).

Synthesis Example 11

The compound 11-1 (14.6 g, 30 mmol) and the compound 11-2 (4.7 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(dba) ₂ (0.6 g), and PCy ₃ (0.6 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from chloroform and ethanol by filtration to prepare Compound 11-3. (10.2 g, yield 62%, MS:[M+H]+=550).

The compound 11-3 (16.5 g, 30 mmol) and the compound 11-4 (4.5 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(PtBu ₃ ) ₂ (0.9 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 11. (13.1 g, yield 72%, MS:[M+H]+=606).

Synthesis Example 12

The compound 12-1 (14.3 g, 30 mmol) and the compound 12-2 (8.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(dba) ₂ (0.6 g), and PCy ₃ (0.6 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from chloroform and ethanol by filtration to prepare Compound 12-3. (10.2 g, yield 51%, MS: [M+H] + = 665).

The compound 12-3 (19.9 g, 30 mmol) and the compound 12-4 (5.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(PtBu ₃ ) ₂ (0.9 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized twice with ethyl acetate by filtration to prepare Compound 12. (13.7 g, yield 62%, MS:[M+H]+= 735).

Synthesis Example 13

The compound 13-1 (13.8 g, 30 mmol) and the compound 13-2 (11.3 mol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(dba) ₂ (0.6 g), and PCy ₃ (0.6 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from chloroform and ethanol by filtration to prepare Compound 13-3. (14.8 g, yield 68%, MS: [M+H] + = 725).

The compound 13-3 (21.7 g, 30 mmol) and the compound 13-4 (6.6 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(PtBu ₃ ) ₂ (0.9 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare the compound 13. (17.2 g, yield 68%, MS:[M+H]+= 844).

Synthesis Example 14

The compound 14-1 (14.6 g, 30 mmol) and the compound 14-2 (9.7, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(dba) ₂ (0.6 g), and PCy ₃ (0.6 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from chloroform and ethanol by filtration to prepare compound 14-3. (14.9 g, yield 71%, MS:[M+H]+=702).

The compound 14-3 (21.0 g, 30 mmol) and the compound 14-4 (7.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(PtBu ₃ ) ₂ (0.9 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 14. (19.5 g, yield 78%, MS: [M+H] + = 835).

Synthesis Example 15

The compound 15-1 (14.3 g, 30 mmol) and the compound 15-2 (8.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(dba) ₂ (0.6 g), and PCy ₃ (0.6 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from chloroform and ethanol by filtration to prepare Compound 15-3. (14.1 g, yield 71%, MS: [M+H] + = 664).

The compound 15-3 (19.9 g, 30 mmol) and the compound 15-4 (4.1 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(PtBu ₃ ) ₂ (0.9 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 15. (15.0 g, yield 71%, MS:[M+H]+=706).

Synthesis Example 16

The compound 16-1 (13.8 g, 30 mmol) and the compound 16-2 (12.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(dba) ₂ (0.6 g), and PCy ₃ (0.6 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from chloroform and ethanol by filtration to prepare the compound 16-3. (17.2 g, yield 78%, MS:[M+H]+=755).

The compound 16-3 (22.6 g, 30 mmol) and the compound 16-4 (4.1 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(PtBu ₃ ) ₂ (0.9 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 16. (10.3 g, yield 43%, MS:[M+H]+=798).

Synthesis Example 17

The compound 17-1 (14.6 g, 30 mmol) and the compound 17-2 (6.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(dba) ₂ (0.6 g), and PCy ₃ (0.6 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from chloroform and ethanol by filtration to prepare compound 17-3. (15.0 g, yield 82%, MS:[M+H]+=612).

The compound 17-3 (18.3 g, 30 mmol) and the compound 17-4 (4.1 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(PtBu ₃ ) ₂ (0.9 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 17. (14.1 g, yield 72%, MS:[M+H]+=654).

Synthesis Example 18

The compound 18-1 (14.3 g, 30 mmol) and the compound 18-2 (4.7 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(dba) ₂ (0.6 g), and PCy ₃ (0.6 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from chloroform and ethanol by filtration to prepare Compound 18-3. (12.7 g, yield 77%, MS:[M+H]+=549).

The compound 18-3 (16.5 g, 30 mmol) and the compound 18-4 (4.5 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(PtBu ₃ ) ₂ (0.9 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 18. (12.9 g, yield 72%, MS: [M+H] + = 596).

Synthesis Example 19

The compound 19-1 (13.8 g, 30 mmol) and the compound 19-2 (11.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(dba) ₂ (0.6 g), and PCy ₃ (0.6 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from chloroform and ethanol by filtration to prepare Compound 19-3. (16.7 g, yield 76%, MS:[M+H]+=734).

The compound 19-3 (22.0 g, 30 mmol) and the compound 19-4 (5.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(PtBu ₃ ) ₂ (0.9 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized twice with ethyl acetate by filtration to prepare Compound 19. (15.5 g, yield 65%, MS:[M+H]+=796).

Synthesis Example 20

The compound 20-1 (9.7 g, 30 mmol) and the compound 20-2 (11.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(dba) ₂ (0.6 g), and PCy ₃ (0.6 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from chloroform and ethanol by filtration to prepare Compound 20-3. (16.7 g, yield 76%, MS:[M+H]+=586).

The compound 20-3 (17.6 g, 30 mmol) and the compound 20-4 (6.6 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(PtBu ₃ ) ₂ (0.9 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 20. (14.6 g, yield 69%, MS:[M+H]+=704).

Synthesis Example 21

The compound 21-1 (13.4 g, 30 mmol) and the compound 21-2 (9.7 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(dba) ₂ (0.6 g), and PCy ₃ (0.6 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from chloroform and ethanol by filtration to prepare Compound 21-3. (15.5 g, yield 78%, MS:[M+H]+=662).

The compound 21-3 (19.8 g, 30 mmol) and the compound 21-4 (7.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(PtBu ₃ ) ₂ (0.9 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 21. (16.9 g, yield 71%, MS:[M+H]+=795).

Synthesis Example 22

The compound 22-1 (13.8 g, 30 mmol) and the compound 22-2 (12.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(dba) ₂ (0.6 g), and PCy ₃ (0.6 g) were added thereto, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from chloroform and ethanol by filtration to prepare Compound 22-3. (18.5 g, yield 85%, MS:[M+H]+= 725).

The compound 22-3 (21.7 g, 30 mmol) and the compound 22-4 (5.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (100 mL), Pd(PtBu ₃ ) ₂ (0.9 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 22. (14.8 g, yield 62%, MS:[M+H]+=795).

[Element example]

Example 1

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 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 cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the thus prepared ITO transparent electrode, the following compound [HI-A] was thermally vacuum-deposited to a thickness of 600 Å to form a hole injection layer. On the hole injection layer, hexanitrile hexaazatriphenylene (HAT) of the following formula was sequentially vacuum-deposited 50 Å and the following compound [HT-A] (600 Å) to form first and second hole transport layers.

Subsequently, the following compounds [BH] and [BD] were vacuum-deposited in a weight ratio of 25:1 to a thickness of 200 Å on the hole transport layer to form a light emitting layer. On the light emitting layer, the compound 1 and [LiQ] (Lithiumquinolate) were vacuum-deposited in a 1:1 weight ratio to form an electron injection and transport layer to a thickness of 350 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.

In the above process, the deposition rate of organic material was maintained at 0.4 ~ 0.9 Å/sec, the deposition rate of lithium fluoride of the negative electrode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum degree during deposition was 1 × 10 ^{By maintaining -7} to 5 × 10 ^-8 torr, an organic light emitting diode was manufactured.

[HAT]

[HI-A] [HT-A]

[BH] [BD]

[LiQ]

Example 2

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 2 was used instead of Compound 1 in Example 1.

Example 3

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 3 was used instead of Compound 1 in Example 1.

Example 4

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 4 was used instead of Compound 1 in Example 1.

Example 5

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 5 was used instead of Compound 1 in Example 1.

Example 6

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 6 was used instead of Compound 1 in Example 1.

Example 7

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 7 was used instead of Compound 1 in Example 1.

Example 8

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 8 was used instead of Compound 1 in Example 1.

Example 9

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 9 was used instead of Compound 1 in Example 1.

Example 10

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 10 was used instead of Compound 1 in Example 1.

Example 11

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 11 was used instead of Compound 1 in Example 1.

Example 12

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 12 was used instead of Compound 1 in Example 1.

Example 13

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 13 was used instead of Compound 1 in Example 1.

Example 14

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 14 was used instead of Compound 1 in Example 1.

Example 15

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 15 was used instead of Compound 1 in Example 1.

Example 16

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 16 was used instead of Compound 1 in Example 1.

Example 17

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 17 was used instead of Compound 1 in Example 1.

Example 18

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 18 was used instead of Compound 1 in Example 1.

Example 19

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 19 was used instead of Compound 1 in Example 1.

Example 20

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 20 was used instead of Compound 1 in Example 1.

Example 21

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 21 was used instead of Compound 1 in Example 1.

Example 22

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 22 was used instead of Compound 1 in Example 1.

Comparative Example 1

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound ET1 was used instead of Compound 1 in Example 1.

[ET1]

Comparative Example 2

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound ET2 was used instead of Compound 1 in Example 1.

[ET2]

Comparative Example 3

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound ET3 was used instead of Compound 1 in Example 1.

[ET3]

Comparative Example 4

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound ET4 was used instead of Compound 1 in Example 1.

[ET4]

As in Examples 1 to 22 and Comparative Examples 1 to 4, the organic light emitting device prepared by using each compound as an electron injection and transport layer material was ^{measured at a current density of 10 mA/cm 2} and the driving voltage and luminous efficiency. and the time (LT98) to be 98% of the initial luminance at a current density of 20 mA/cm ^{2 was measured.}

The results are shown in Table 1 below.

division compound Voltage
(V) current efficiency
(cd/A) Life Time 98 at 20mA/cm ² Example 1 compound 1 3.48 5.51 65 Example 2 compound 2 3.60 5.50 75 Example 3 compound 3 3.71 5.32 80 Example 4 compound 4 3.75 5.30 65 Example 5 compound 5 3.63 5.21 80 Example 6 compound 6 3.83 5.50 75 Example 7 compound 7 3.45 5.24 60 Example 8 compound 8 3.75 5.05 60 Example 9 compound 9 3.72 5.12 75 Example 10 compound 10 3.83 5.14 80 Example 11 compound 11 3.91 5.21 70 Example 12 compound 12 4.01 5.22 65 Example 13 compound 13 3.53 5.35 80 Example 14 compound 14 3.78 5.24 75 Example 15 compound 15 3.88 5.26 60 Example 16 compound 16 3.69 5.38 75 Example 17 compound 17 3.78 5.49 75 Example 18 compound 18 3.77 5.50 70 Example 19 compound 19 3.70 5.51 65 Example 20 compound 20 3.81 5.30 65 Example 21 compound 21 3.88 5.33 80 Example 22 compound 22 3.78 5.21 80 Comparative Example 1 ET1 4.35 4.52 35 Comparative Example 2 ET2 5.00 3.50 70 Comparative Example 3 ET3 4.91 4.25 50 Comparative Example 4 ET4 4.80 3.01 30

As can be seen from the experimental data of Table 1, in the case of the organic light emitting device using the compound of Formula 1 according to the present invention, it was confirmed that it exhibited excellent characteristics in terms of efficiency, driving voltage and/or stability.

It can be seen that in Comparative Example 1 at which positions L1 and L4 of Formula 1 of the present invention are connected to Formula 1-2 are different, the driving voltage is high and the efficiency and lifespan are reduced.

It can be seen that the driving voltage is high and the efficiency is decreased in Comparative Example 2, which does not contain the triazine or pyrimidine of the present invention and includes two pyridine groups.

It can be seen that in Comparative Example 3, which does not contain the triazine or pyrimidine of the present invention and contains only one pyridine group, the driving voltage is high and the efficiency and lifespan are reduced.

In the case of Comparative Example 4 in which both Cy1 and Cy2 of Chemical Formula 1 of the present invention are benzene rings, it can be seen that the driving voltage is high and the efficiency and lifespan are reduced.

101: substrate
102: positive electrode
103: hole injection layer
104: first hole transport layer
105: second hole transport layer
106: light emitting layer
107: electron injection and transport layer
108: cathode

Claims (13)

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

In Formula 1,
At least 2 or more of X1 to X3 are N, the rest are CH,
L1 to L4 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,
Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
n1 to n4 are integers from 0 to 4,
m1 is an integer from 0 to 4,
When n1 to n4 and m1 are each 2 or more, the substituents in parentheses are the same or different from each other,
A1 is represented by the following formula 1-1 or 1-2,
[Formula 1-1] [Formula 1-2]

In Formula 1-1,
Any one of Cy1 and Cy2 is a naphthalene ring, and the other is a benzene ring,
G1 is a direct bond or -C(R17)(R18)-; -O-; or -S-;
any one of R11 to R14 is connected to L1 of Formula 1, the other is connected to L4 of Formula 1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R17 and R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
r11 and r13 are integers from 0 to 4,
any one of r12 and r14 is an integer from 0 to 6, the other is an integer from 0 to 4,
When each of r11 to r14 is 2 or more, the substituents in parentheses are the same or different from each other,
In Formula 1-2,
Cy3 is a naphthalene ring,
Ar4 and Ar5 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
any one of R15 and R16 is connected to L1 of Formula 1, the other is connected to L4 of Formula 1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
r15 is an integer from 0 to 4,
r16 is an integer from 0 to 6,
When r15 and r16 are each 2 or more, the substituents in parentheses are the same as or different from each other. The heterocyclic compound according to claim 1, wherein Formula 1-1 is represented by Formula A11 or A12, and Formula 1-2 is represented by Formula A21:
[Formula A11] [Formula A12]

[Formula A21]

In the formulas A11 and A12,
The definition of G1 is as defined in Formula 1-1,
any one of R21 to R38 is connected to L1 of Formula 1, the other is connected to L4 of Formula 1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
In the formula A21,
Ar4 and Ar5 are the same as defined in Formula 1-2,
any one of R41 to R50 is connected to L1 of Formula 1, the other is connected to L4 of Formula 1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group. The heterocyclic compound according to claim 1, wherein Chemical Formula 1-1 is represented by any one of the following Chemical Formulas A13 to A18:
[Formula A13] [Formula A14]

[Formula A15] [Formula A16]

[Formula A17] [Formula A18]

In the formulas A13 to A18,
The definition of G1 is as defined in Formula 1-1,
any one of R21 to R38 is connected to L1 of Formula 1, the other is connected to L4 of Formula 1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group. The heterocyclic compound according to claim 1, wherein Chemical Formula 1-2 is represented by any one of the following Chemical Formulas A22 to A24:
[Formula A22] [Formula A23]

[Formula A24]

In the formulas A22 to A24,
Ar4 and Ar5 are the same as defined in Formula 1-2,
any one of R41 to R50 is connected to L1 of Formula 1, the other is connected to L4 of Formula 1, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group. The heterocyclic compound according to claim 1, wherein A1 is a divalent group selected from the following groups 1 to 9:
[Group 1]

[Group 2]

[Group 3]

[Group 4]

[Group 5]

[Group 6]

[Group 7]

[Group 8]

[Group 9]

In groups 1 to 9,
G1 is a direct bond or -C(R17)(R18)-; -O-; or -S-;
Ar4 and Ar5 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
The structure is deuterium; cyano group; an alkyl group; aryl group; Or substituted or unsubstituted with a heteroaryl group,

is a position connected to L1 or L4 of Formula 1; The heterocyclic compound according to claim 1, wherein L1 to L4 are the same as or different from each other, and are each independently selected from a direct bond or the following structure:

. The heterocyclic compound of claim 1, wherein at least one of L1 and L4 is a direct bond. The method according to claim 1,
L1 to L4 are the same as or different from each other, and each independently a direct bond; Or a C6-C30 arylene group,
Ar1 to Ar3 are the same as or different from each other, and each independently a C1-C10 alkyl group; a C6-C30 aryl group unsubstituted or substituted with a C1-C10 alkyl group or a C2-C30 heteroaryl group; Or a C2-C30 heteroaryl group,
of R11 to R14, the remainder not connected to Formulas L1 and L4 may be the same as or different from each other, and each independently hydrogen; or deuterium,
R17 and R18 are the same as or different from each other, and each independently represents a C1-C10 alkyl group,
Ar4 and Ar5 are the same as or different from each other, and each independently a C1-C10 alkyl group; Or a C6-C30 aryl group,
R15 and R16, the remainder not connected to Formulas L1 and L4 are the same as or different from each other, and each independently hydrogen; Or a heterocyclic compound that is deuterium. The heterocyclic compound according to claim 1, wherein the heterocyclic compound represented by Formula 1 is any one selected from the following compounds:

. a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer comprises the heterocyclic compound according to any one of claims 1 to 9 Phosphorus organic light emitting device. The method according to claim 10, wherein the organic layer comprises an electron injection layer, an electron transport layer, an electron injection and transport layer or a hole blocking layer, the electron injection layer, the electron transport layer, the electron injection and transport layer or the hole blocking layer comprises the heterocyclic compound an organic light emitting device. The organic light emitting diode of claim 11 , wherein the electron injection layer, the electron transport layer, the electron injection and transport layer, or the hole blocking layer further include an n-type dopant. The organic material layer of claim 10, further comprising one or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. light emitting element.

Images