KR102656592B1 - Organic compound, organic light emitting device comprising the same and composition for organic layer of organic light emitting device - Google Patents

Abstract

This specification relates to an organic compound represented by Formula 1, an organic light-emitting device containing the same, and a composition for an organic material layer of the organic light-emitting device.

Description

Organic compound, organic light-emitting device containing the same, and composition for the organic layer of the organic light-emitting device {ORGANIC COMPOUND, ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME AND COMPOSITION FOR ORGANIC LAYER OF ORGANIC LIGHT EMITTING DEVICE}

The present invention relates to organic compounds, organic light-emitting devices containing the same, and compositions for organic material layers of organic light-emitting devices.

Organic light emitting devices are a type of self-emitting display devices and have the advantages of a wide viewing angle, excellent contrast, and fast response speed.

Organic light-emitting devices have a structure in which an organic thin film is placed between two electrodes. When voltage is applied to an organic light emitting device with this structure, electrons and holes injected from two electrodes combine in the organic thin film to form a pair and then disappear, emitting light. The organic thin film may be composed of a single layer or multiple layers, depending on need.

The material of the organic thin film may have a light-emitting function as needed. For example, as an organic thin film material, a compound that can independently form a light-emitting layer may be used, or a compound that can act as a host or dopant of a host-dopant-based light-emitting layer may be used. In addition, as a material for the organic thin film, compounds that can perform roles such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection may be used.

In order to improve the performance, lifespan, or efficiency of organic light-emitting devices, the development of organic thin film materials is continuously required.

US Patent No. 4,356,429

The present invention seeks to provide an organic compound, an organic light-emitting device containing the same, and a composition for the organic material layer of the organic light-emitting device.

The present invention provides an organic compound represented by the following formula (1):

[Formula 1]

In Formula 1,

R1 to R12 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; A group represented by the following formula 1-1; And it is selected from the group consisting of a group represented by the following formula 1-2,

[Formula 1-1]

In Formula 1-1,

R21 and R22 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group,

L1 is a single bond; Substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group;

m is an integer from 0 to 5, and when m is 2 or more, L1 is the same as or different from each other,

[Formula 1-2]

In Formula 1-2,

X1 is N or CRa,

X2 is N or CRb,

X3 is N or CRc,

X4 is N or CRd,

X5 is N or CRe,

At least one of X1 to X5 is N,

Ra to Re are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Or a substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group, or a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring where two or more adjacent groups are bonded to each other; Or a substituted or unsubstituted C2 to C60 hetero ring;

L2 is a single bond; Substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group;

n is an integer from 0 to 5, and when n is 2 or more, L2 is the same as or different from each other.

In addition, the present invention includes a first electrode; a second electrode provided opposite the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layers includes an organic compound represented by Formula 1. .

Additionally, the present invention provides a composition for the organic material layer of an organic light-emitting device containing two or more types of organic compounds according to the present invention.

According to one embodiment, an organic compound using the organic compound represented by Formula 1 has an improved hole transport ability by using conjugation expansion, and has the effect of improving the efficiency and lifespan of an organic light-emitting device due to structural stability.

More specifically, when the organic compound according to one embodiment is used as a light-emitting layer or a light-emitting auxiliary layer, hole transport and electron transport characteristics are strengthened, and band gap and triplet energy are improved. By adjusting the level (T1 level) value, the hole transport ability is improved, the stability of the molecule is increased, the driving voltage of the organic light-emitting device is lowered, the luminous efficiency is improved, and the lifespan of the organic light-emitting device is increased by the improved thermal stability of the compound. Improves characteristics.

1 to 3 are diagrams schematically showing the stacked structure of an organic light-emitting device according to an embodiment of the present invention.

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

In this specification, the term “substitution” means changing the hydrogen atom bonded to the carbon atom of the compound to another substituent, and the position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted. , when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

In this specification, “substituted or unsubstituted” means deuterium; halogen; cyano; C1 to C60 straight or branched alkyl; C2 to C60 straight or branched alkenyl; C2 to C60 straight or branched. Chain alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; - SiRR'R"; -P(=O)RR'; C1 to C20 alkylamine; C6 to C60 monocyclic or polycyclic arylamine; and C2 to C60 monocyclic or polycyclic heteroarylamine.

In this specification, the halogen may be fluorine, chlorine, bromine, or iodine.

In the present specification, the alkyl group includes a straight chain or branched chain having 1 to 60 carbon atoms, and may be further substituted by another substituent. The carbon number of the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically, 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethyl heptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, etc., but is not limited thereto.

In the present specification, the alkenyl group includes a straight chain or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The alkenyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms. Specific examples include vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1 -Butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but is not limited to these.

In the present specification, the alkynyl group includes a straight chain or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The carbon number of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically, 2 to 20.

In the present specification, the alkoxy group may be straight chain, branched chain, or ring chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n. -It can be hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. It is not limited.

In the present specification, the cycloalkyl group includes a monocyclic or polycyclic ring having 3 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic refers to a group in which a cycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may also be another type of ring group, such as a heterocycloalkyl group, an aryl group, or a heteroaryl group. The carbon number of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2 , 3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, etc., but is not limited thereto.

In the present specification, the heterocycloalkyl group contains O, S, Se, N or Si as a hetero atom, contains a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic refers to a group in which a heterocycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may also be another type of ring group, such as a cycloalkyl group, an aryl group, or a heteroaryl group. The carbon number of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

In the present specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic refers to a group in which an aryl group is directly connected to or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be another type of ring group, such as a cycloalkyl group, heterocycloalkyl group, heteroaryl group, etc. The aryl group includes a spiro group. The aryl group may have 6 to 60 carbon atoms, specifically 6 to 40 carbon atoms, and more specifically 6 to 25 carbon atoms. Specific examples of the aryl group include phenyl group, biphenyl group, triphenyl group, naphthyl group, anthryl group, chrysenyl group, phenanthrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, phenalenyl group, and pyrethyl group. Nyl group, tetracenyl group, pentacenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, and condensed rings thereof These may include, but are not limited to this.

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

When the fluorenyl group is substituted, , , , , , It may be, but is not limited to this.

In the present specification, the heteroaryl group includes S, O, Se, N, or Si as a hetero atom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, the polycyclic refers to a group in which a heteroaryl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be another type of ring group, such as a cycloalkyl group, heterocycloalkyl group, or aryl group. The carbon number of the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of the heteroaryl group include pyridyl group, pyrrolyl group, pyrimidyl group, pyridazinyl group, furanyl group, thiophene group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, and thiazolyl group. group, isothiazolyl group, triazolyl group, furazanyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazinyl group, oxazinyl group , thiazinyl group, deoxynyl group, triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolyryl group, naphthyridyl group, acridinyl group, phenanthridide Nyl group, imidazopyridinyl group, diazanaphthalenyl group, triazindene group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophene group, benzofuran group , dibenzothiophene group, dibenzofuran group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilol group, spirobi (dibenzosilol), dihydrophenazinyl group, Phenoxazinyl group, phenanthridyl group, imidazopyridinyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10, 11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiathiazinyl group, phthalazinyl group, naphthylidinyl group, phenanthrolinyl group, Benzo[c][1,2,5]thiadiazolyl group, 5,10-dihydrodibenzo[b,e][1,4]azacylinyl, pyrazolo[1,5-c]quinazolinyl group , pyrido [1,2-b] indazolyl group, pyrido [1,2-a] imidazo [1,2-e] indolinyl group, 5,11-dihydroindeno [1,2-b ] Carbazolyl group, etc. may be mentioned, but it is not limited thereto.

In the present specification, the amine group is a monoalkylamine group; monoarylamine group; Monoheteroarylamine group; -NH ₂ ; dialkylamine group; Diarylamine group; Diheteroarylamine group; Alkylarylamine group; Alkylheteroarylamine group; and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, dibiphenylamine group, anthracenylamine group, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenyl fluorescein Examples include a nylamine group, phenyltriphenylenylamine group, and biphenyltriphenylenylamine group, but are not limited to these.

In the present specification, an arylene group refers to an aryl group having two bonding positions, that is, a bivalent group. The description of the aryl group described above can be applied, except that each of these is a divalent group. In addition, a heteroarylene group means that a heteroaryl group has two bonding positions, that is, a bivalent group. The description of the heteroaryl group described above can be applied, except that each of these is a divalent group.

As used herein, an “adjacent” group may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the substituent in terms of structure, or another substituent substituted on the atom on which the substituent is substituted. You can. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as “adjacent” groups.

In the present invention, “if a substituent is not indicated in the chemical formula or compound structure” means that a hydrogen atom is bonded to a carbon atom. However, since deuterium (2H, Deuterium) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

In one embodiment of the present invention, “when a substituent is not indicated in the chemical formula or compound structure” may mean that all positions that can appear as substituents are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be the isotope deuterium, and in this case, the content of deuterium may be 0% to 100%.

In one embodiment of the present invention, in “cases where substituents are not indicated in the chemical formula or compound structure,” “content of deuterium is 0%,” “content of hydrogen is 100%,” “substituents are all hydrogen,” etc. If deuterium is not explicitly excluded, hydrogen and deuterium can be used together in a compound.

In one embodiment of the present invention, deuterium is one of the isotopes of hydrogen and is an element that has a deuteron consisting of one proton and one neutron as its nucleus. Hydrogen- It can be expressed as 2, and the element symbol can also be written as D or 2H.

In one embodiment of the present invention, isotopes refer to atoms having the same atomic number (Z) but different mass numbers (A). Isotopes have the same number of protons but do not contain neutrons. It can also be interpreted as an element with a different number of neutrons.

In one embodiment of the present invention, the meaning of the content T% of a specific substituent means that the total number of substituents that the basic compound can have is defined as T1, and the number of specific substituents among them is defined as T2. It can be defined as /T1×100 = T%.

That is, in one example, The deuterium content of 20% in the phenyl group represented by can mean that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and the number of deuteriums among them is 1 (T2 in the formula). . That is, it can be expressed by the following structural formula, which means that the deuterium content in the phenyl group is 20%.

Additionally, in one embodiment of the present invention, “a phenyl group with a deuterium content of 0%” may mean a phenyl group that does not contain deuterium atoms, that is, has 5 hydrogen atoms.

In the present invention, the C6 to C60 aromatic hydrocarbon ring refers to a compound containing an aromatic ring consisting of C6 to C60 carbons and hydrogen, for example, benzene, biphenyl, triphenyl, triphenylene, naphthalene, Anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene, etc. may be mentioned, but are not limited to these, and aromatic hydrocarbon ring compounds known in the art that satisfy the above carbon number may be used. Includes all.

The present invention provides an organic compound represented by the following formula (1):

[Formula 1]

In Formula 1,

R1 to R12 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; A group represented by the following formula 1-1; And it is selected from the group consisting of a group represented by the following formula 1-2,

[Formula 1-1]

In Formula 1-1,

R21 and R22 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group,

L1 is a single bond; Substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group;

m is an integer from 0 to 5, and when m is 2 or more, L1 is the same as or different from each other,

[Formula 1-2]

In Formula 1-2,

X1 is N or CRa,

X2 is N or CRb,

X3 is N or CRc,

X4 is N or CRd,

X5 is N or CRe,

At least one of X1 to X5 is N,

Ra to Re are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Or a substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group, or a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring where two or more adjacent groups are bonded to each other; Or a substituted or unsubstituted C2 to C60 hetero ring;

L2 is a single bond; Substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group;

n is an integer from 0 to 5, and when n is 2 or more, L2 is the same as or different from each other.

In one embodiment of the present invention, R1 to R12 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C30 alkyl group; Substituted or unsubstituted C2 to C30 alkenyl group; Substituted or unsubstituted C2 to C30 alkynyl group; Substituted or unsubstituted C1 to C30 alkoxy group; Substituted or unsubstituted C3 to C30 cycloalkyl group; Substituted or unsubstituted C2 to C30 heterocycloalkyl group; Substituted or unsubstituted C6 to C30 aryl group; Substituted or unsubstituted C2 to C30 heteroaryl group; A group represented by Formula 1-1; and a group represented by Formula 1-2.

In another embodiment of the present invention, at least one of R1 to R12 may be a group represented by Formula 1-1 or a group represented by Formula 1-2.

In another embodiment of the present invention, at least one of R1 to R6 is a group represented by Formula 1-1 or a group represented by Formula 1-2, and at least one of R7 to R12 is a substituted or unsubstituted C6 to C30. It may be an aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group.

In another embodiment of the present invention, at least one of R1 to R6 is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, and at least one of R7 to R12 has the formula It may be a group represented by 1-1 or a group represented by Formula 1-2.

In one embodiment of the present invention, in Formula 1-1, R21 and R22 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C30 alkyl group; Substituted or unsubstituted C2 to C30 alkenyl group; Substituted or unsubstituted C2 to C30 alkynyl group; Substituted or unsubstituted C1 to C30 alkoxy group; Substituted or unsubstituted C6 to C30 aryl group; and a substituted or unsubstituted C2 to C30 heteroaryl group.

In another embodiment of the present invention, in Formula 1-1, R21 and R22 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 aryl group. It may be a heteroaryl group.

In another embodiment of the present invention, in Formula 1-1, R21 and R22 are the same or different from each other, and each independently represents a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 benzo group. Furan group, substituted or unsubstituted C2 to C30 dibenzofuran group, substituted or unsubstituted C2 to C30 benzothiophene group, substituted or unsubstituted C2 to C30 dibenzothiophene group, substituted or unsubstituted It may be a C2 to C30 carbazolyl group, or a substituted or unsubstituted C2 to C30 benzocarbazolyl group.

In one embodiment of the present invention, in Formula 1-1, L1 is a single bond; Substituted or unsubstituted C6 to C30 arylene group; Or it may be a substituted or unsubstituted C2 to C30 heteroarylene group.

In another embodiment of the present invention, in Formula 1-1, L1 is a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 dibenzofuranylene group, or a substituted or unsubstituted It may be a ringed C2 to C30 dibenzothiophenylene group.

In another embodiment of the present invention, in Formula 1-1, when m is an integer of 2 or more, L1 is a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or , It may be a combination of a substituted or unsubstituted C6 to C30 arylene group and a substituted or unsubstituted C2 to C30 heteroarylene group.

In another embodiment of the present invention, in Formula 1-1, when m is an integer of 2 or more, L1 is a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 dibenzofuranyl group. It is a lene group, a substituted or unsubstituted C2 to C30 dibenzothiophenylene group, a combination of a substituted or unsubstituted C6 to C30 arylene group and a substituted or unsubstituted C2 to C30 dibenzofuranylene group, or a substituted Alternatively, it may be a combination of an unsubstituted C6 to C30 arylene group and a substituted or unsubstituted C2 to C30 dibenzothiophenylene group.

In one embodiment of the present invention, in Formula 1-1, m may be an integer from 0 to 5.

In another embodiment of the present invention, when m is 0, L1 may be a single bond.

In another embodiment of the present invention, when m is 2, L1 may be the same or different from each other.

In one embodiment of the present invention, the 'substitution' of L1, R21 and R22 is deuterium; halogen; Cyano group; C1 to C10 alkyl group; C2 to C10 alkenyl group; C2 to C10 alkynyl group; C3 to C15 cycloalkyl group; C2 to C20 heterocycloalkyl group; Aryl group of C6 to C30; Each may independently consist of one or more substituents selected from the group consisting of C2 to C30 heteroaryl groups.

In another embodiment of the present invention, the 'substitution' of L1, R21 and R22 is deuterium; halogen; Cyano group; C1 to C10 alkyl group; Aryl group of C6 to C30; Each may independently consist of one or more substituents selected from the group consisting of C2 to C30 heteroaryl groups.

In another embodiment of the present invention, the 'substitution' of L1, R21 and R22 is deuterium; halogen; Cyano group; C1 to C5 alkyl group; Aryl group of C6 to C20; and one or more substituents selected from the group consisting of C2 to C20 heteroaryl groups.

In another embodiment of the present invention, the 'substitution' of L1, R21 and R22 is deuterium, halogen, cyano group, methyl group, ethyl group, straight or branched propyl group, straight or branched butyl group, straight or branched. One or more substituents selected from the group consisting of pentyl group, phenyl group, naphthalenyl group, pyridinyl group, anthracenyl group, carbazole group, benzocarbazole group, dibenzothiophene group, dibenzofuran group, and phenanthrenyl group in the chain. Each can be done independently.

In one embodiment of the present invention, in Formula 1-2, X1 is N or CRa, X2 is N or CRb, X3 is N or CRc, X4 is N or CRd, X5 is N or CRe, At least one of X1 to X5 is N, Ra to Re are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C30 alkyl group; Substituted or unsubstituted C2 to C30 alkenyl group; Substituted or unsubstituted C2 to C30 alkynyl group; Or a substituted or unsubstituted C1 to C30 alkoxy group; Substituted or unsubstituted C6 to C30 aryl group; and a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring where two or more adjacent groups are bonded to each other; Alternatively, it may form a substituted or unsubstituted C2 to C30 hetero ring.

In another embodiment of the present invention, the group represented by Formula 1-2 may be any one of the following Formulas 1-2-a to 1-2-d, but is not limited to these examples:

[Formula 1-2-a]

[Formula 1-2-b]

[Formula 1-2-c]

[Formula 1-2-d]

In Formulas 1-2-a to 1-2-d,

L2, X1 to X5 and n are as defined in Formula 1-2 above,

X6 and X7 are C, O or S,

a is 0 or 1, and when a is 1, it forms a T1 ring or a T2 ring,

The T1 ring and the T2 ring are the same or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aromatic ring; Or a substituted or unsubstituted C2 to C60 heteroaromatic ring,

R31 to R35 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Or a substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group, or a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring where two or more adjacent groups are bonded to each other; Or a substituted or unsubstituted C2 to C60 hetero ring;

p is an integer from 0 to 4,

q is an integer from 0 to 3,

When a is 0, r is an integer from 0 to 4, and when a is 1, r is an integer from 0 to 3.

In another embodiment of the present invention, in Formulas 1-2-a to 1-2-d, when X6 and X7 are C and a is 1, a T1 ring or a T2 ring may be formed, and the T1 The rings or T2 rings are the same or different from each other, and each independently represents a substituted or unsubstituted C6 to C30 aromatic ring; Or it may be a substituted or unsubstituted C2 to C30 heteroaromatic ring.

In another embodiment of the present invention, the T1 ring or T2 ring is the same as or different from each other, and each independently includes a substituted or unsubstituted C6 to C10 aromatic ring; Or, it may be a substituted or unsubstituted C2 to C10 heteroaromatic ring.

In another embodiment of the present invention, in Formulas 1-2-a to 1-2-d, R31 to R35 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C30 alkyl group; Substituted or unsubstituted C2 to C30 alkenyl group; Substituted or unsubstituted C2 to C30 alkynyl group; Or a substituted or unsubstituted C1 to C30 alkoxy group; Substituted or unsubstituted C6 to C30 aryl group; and a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring where two or more adjacent groups are bonded to each other; Alternatively, it may form a substituted or unsubstituted C2 to C30 hetero ring.

In another embodiment of the present invention, in Formulas 1-2-a to 1-2-d, R31 to R35 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C10 alkyl group; Substituted or unsubstituted C2 to C10 alkenyl group; Substituted or unsubstituted C2 to C10 alkynyl group; Or a substituted or unsubstituted C1 to C10 alkoxy group; Substituted or unsubstituted C6 to C10 aryl group; and a substituted or unsubstituted C2 to C10 heteroaryl group, or a substituted or unsubstituted C6 to C10 aromatic hydrocarbon ring where two or more adjacent groups are bonded to each other; Alternatively, it may form a substituted or unsubstituted C2 to C10 hetero ring.

In another embodiment of the present invention, in Formulas 1-2-a to 1-2-d, R31 to R35 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C6 to C10 aryl group; and a substituted or unsubstituted C2 to C10 heteroaryl group, or a substituted or unsubstituted C6 to C10 aromatic hydrocarbon ring in which two or more adjacent groups are bonded to each other; Alternatively, it may form a substituted or unsubstituted C2 to C10 hetero ring.

In one embodiment of the present invention, the group represented by Formula 1-2 may be any one of the groups represented by the following Formulas 1-2-1 to 1-2-4, but is not limited to these examples:

[Formula 1-2-1]

[Formula 1-2-2]

[Formula 1-2-3]

[Formula 1-2-4]

In Formulas 1-2-1 to 1-2-4, Ra to Rd are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C30 alkyl group; Substituted or unsubstituted C2 to C30 alkenyl group; Substituted or unsubstituted C2 to C30 alkynyl group; Or a substituted or unsubstituted C1 to C30 alkoxy group; Substituted or unsubstituted C6 to C30 aryl group; and a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring where two or more adjacent groups are bonded to each other; Or it forms a substituted or unsubstituted C2 to C30 hetero ring, and L2 and n are as defined in Formula 1-2 above.

In another embodiment of the present invention, in Formulas 1-2-1 to 1-2-4, Ra to Rd are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C6 to C30 aryl group; and a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring where two or more adjacent groups are bonded to each other; Or it forms a substituted or unsubstituted C2 to C30 hetero ring, and L2 and n are as defined in Formula 1-2 above.

In one embodiment of the present invention, the group represented by Formula 1-2-1 may be any one of the groups represented by the following Formulas 1-2-1-a to 1-2-1-g, but these examples are limited to It is not limited to:

[Formula 1-2-1-a]

[Formula 1-2-1-b]

[Formula 1-2-1-c]

[Formula 1-2-1-d]

[Formula 1-2-1-e]

[Formula 1-2-1-f]

[Formula 1-2-1-g]

In the above formulas 1-2-1-a to 1-2-1-g,

R41 to R46 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C30 alkyl group; Substituted or unsubstituted C2 to C30 alkenyl group; Substituted or unsubstituted C2 to C30 alkynyl group; Or a substituted or unsubstituted C1 to C30 alkoxy group; Substituted or unsubstituted C6 to C30 aryl group; and a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring where two or more adjacent groups are bonded to each other; or a substituted or unsubstituted C2 to C30 hetero ring; is an integer, d1 is an integer from 0 to 7, e1 is an integer from 0 to 5, f1 is an integer from 0 to 7, and L2 and n are as defined in Formula 1-2 above.

In one embodiment of the present invention, the group represented by Formula 1-2-2 may be any one of the groups represented by Formulas 1-2-2-a to 1-2-2-d, but these examples are limited to It is not limited to:

[Formula 1-2-2-a]

[Formula 1-2-2-b]

[Formula 1-2-2-c]

[Formula 1-2-2-d]

In the above formulas 1-2-2-a to 1-2-2-d,

R51 to R53 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C30 alkyl group; Substituted or unsubstituted C2 to C30 alkenyl group; Substituted or unsubstituted C2 to C30 alkynyl group; Or a substituted or unsubstituted C1 to C30 alkoxy group; Substituted or unsubstituted C6 to C30 aryl group; and a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring where two or more adjacent groups are bonded to each other; or a substituted or unsubstituted heterocyclic ring of C2 to C30; It is an integer, and L2 and n are as defined in Formula 1-2 above.

In one embodiment of the present invention, the group represented by Formula 1-2-3 may be any one of the groups represented by the following Formulas 1-2-3-a to 1-2-3-d, but these are only examples. It is not limited to:

[Formula 1-2-3-a]

[Formula 1-2-3-b]

[Formula 1-2-3-c]

[Formula 1-2-3-d]

In the above formulas 1-2-3-a to 1-2-3-d,

R61 to R63 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C30 alkyl group; Substituted or unsubstituted C2 to C30 alkenyl group; Substituted or unsubstituted C2 to C30 alkynyl group; Or a substituted or unsubstituted C1 to C30 alkoxy group; Substituted or unsubstituted C6 to C30 aryl group; and a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring where two or more adjacent groups are bonded to each other; or a substituted or unsubstituted heterocyclic ring of C2 to C30; It is an integer, and L2 and n are as defined in Formula 1-2 above.

In one embodiment of the present invention, in Formula 1-2, L2 is a single bond; Substituted or unsubstituted C6 to C30 arylene group; Or it may be a substituted or unsubstituted C2 to C30 heteroarylene group.

In another embodiment of the present invention, in Formula 1-2, L2 is a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 dibenzofuranylene group, or a substituted or unsubstituted It may be a ringed C2 to C30 dibenzothiophenylene group.

In another embodiment of the present invention, in Formula 1-2, when n is an integer of 2 or more, L2 is a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or , It may be a combination of a substituted or unsubstituted C6 to C30 arylene group and a substituted or unsubstituted C2 to C30 heteroarylene group.

In another embodiment of the present invention, in Formula 1-2, when n is an integer of 2 or more, L2 is a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 dibenzofuranyl group. It is a lene group, a substituted or unsubstituted C2 to C30 dibenzothiophenylene group, a combination of a substituted or unsubstituted C6 to C30 arylene group and a substituted or unsubstituted C2 to C30 dibenzofuranylene group, or a substituted Alternatively, it may be a combination of an unsubstituted C6 to C30 arylene group and a substituted or unsubstituted C2 to C30 dibenzothiophenylene group.

In one embodiment of the present invention, in Formula 1-2, n may be an integer from 0 to 5.

In another embodiment of the present invention, when n is 0, L2 may be a single bond.

In another embodiment of the present invention, when n is 2 or more, L2 may be the same or different from each other.

In one embodiment of the present invention, the 'substitution' of L2, Ra to Re, R31 to R35, R41 to R46, R51 to R53 and R61 to R63 is deuterium; halogen; Cyano group; C1 to C10 alkyl group; C2 to C10 alkenyl group; C2 to C10 alkynyl group; C3 to C15 cycloalkyl group; C2 to C20 heterocycloalkyl group; Aryl group of C6 to C30; Each may independently consist of one or more substituents selected from the group consisting of C2 to C30 heteroaryl groups.

In another embodiment of the present invention, the 'substitution' of L2, Ra to Re, R31 to R35, R41 to R46, R51 to R53 and R61 to R63 is deuterium; halogen; Cyano group; C1 to C10 alkyl group; Aryl group of C6 to C30; Each may independently consist of one or more substituents selected from the group consisting of C2 to C30 heteroaryl groups.

In another embodiment of the present invention, the 'substitution' of L2, Ra to Re, R31 to R35, R41 to R46, R51 to R53 and R61 to R63 is deuterium; halogen; Cyano group; C1 to C5 alkyl group; Aryl group of C6 to C30; and one or more substituents selected from the group consisting of C2 to C30 heteroaryl groups.

In another embodiment of the present invention, the 'substitution' of L2, Ra to Re, R31 to R35, R41 to R46, R51 to R53 and R61 to R63 is deuterium, halogen, cyano group, methyl group, ethyl group, straight chain or branched. Chain propyl group, straight or branched butyl group, straight or branched pentyl group, phenyl group, naphthalenyl group, pyridinyl group, anthracenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, Indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, other carbazole derivatives, benzothiophene group, dibenzothiophene group, dibenzofuran group, and phenanthre. Each may independently consist of one or more substituents selected from the group consisting of a nyl group.

In one embodiment of the present invention, the content of deuterium may be 0% to 100% based on the total number of hydrogen atoms and deuterium atoms in the organic compound represented by Formula 1.

In another embodiment of the present invention, the content of deuterium may be 1% to 100% based on the total number of hydrogen atoms and deuterium atoms in the organic compound represented by Formula 1.

In another embodiment of the present invention, the content of deuterium may be 10% to 90% based on the total number of hydrogen atoms and deuterium atoms in the organic compound represented by Formula 1.

In another embodiment of the present invention, the content of deuterium may be 20% to 80% based on the total number of hydrogen atoms and deuterium atoms in the organic compound represented by Formula 1.

For example, based on the total number of hydrogen atoms and deuterium atoms in the organic compound represented by Formula 1, the deuterium content is 0% or more, 1% or more, 5% or more, 10% or more, 15% or more, or 20% or more. , may be 25% or more, 30% or more, 35% or more, 40% or more, 45% or more, or 50% or more, and may be 100% or less, 95% or less, 90% or less, 85% or less, 80% or less, 75% or less. It may be 70% or less, 65% or less, or 60% or less.

In one embodiment of the present invention, the organic compound represented by Formula 1 may be any one selected from the group consisting of the following compounds:

Additionally, by introducing various substituents into the structure of Formula 1, a compound having the unique properties of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection layer materials, hole transport layer materials, light emitting layer materials, electron transport layer materials, and charge generation layer materials used in the manufacture of organic light-emitting devices into the core structure, the conditions required for each organic material layer are met. Materials can be synthesized.

In addition, by introducing various substituents into the structure of Formula 1, the energy band gap can be finely adjusted, while the properties at the interface between organic materials can be improved and the uses of the material can be diversified.

Additionally, in one embodiment of the present invention, a first electrode; a second electrode provided opposite to the first electrode; and an organic light emitting device comprising 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 includes an organic compound represented by Formula 1. do.

In one embodiment of the present invention, the first electrode may be an anode, and the second electrode may be a cathode.

In another embodiment, the first electrode may be a cathode, and the second electrode may be an anode.

In one embodiment of the present invention, the organic light-emitting device may be a blue organic light-emitting device, and the organic compound represented by Formula 1 may be used as a material for the blue organic light-emitting device.

In one embodiment of the present invention, the organic light-emitting device may be a green organic light-emitting device, and the organic compound represented by Formula 1 may be used as a material for the green organic light-emitting device.

In one embodiment of the present invention, the organic light-emitting device may be a red organic light-emitting device, and the organic compound represented by Formula 1 may be used as a material for the red organic light-emitting device.

In one embodiment of the present invention, the organic light-emitting device may be a blue organic light-emitting device, and the organic compound represented by Formula 1 may be used as a light-emitting layer material of the blue organic light-emitting device.

In one embodiment of the present invention, the organic light-emitting device may be a green organic light-emitting device, and the organic compound represented by Formula 1 may be used as a light-emitting layer material of the green organic light-emitting device.

In one embodiment of the present invention, the organic light-emitting device may be a red organic light-emitting device, and the organic compound represented by Formula 1 may be used as a light-emitting layer material of the red organic light-emitting device.

Specific details about the organic compound represented by Formula 1 are the same as described above.

The organic light emitting device of the present invention can be manufactured using conventional organic light emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the above-described organic compounds.

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

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

In one embodiment of the present invention, the organic light-emitting device may include one or more organic material layers, the organic material layer may include a light-emitting layer or a light-emitting auxiliary layer, and the light-emitting layer or the light-emitting auxiliary layer is represented by Formula 1 It may contain organic compounds that are

In another embodiment of the present invention, the organic material layer may include a light-emitting layer or a light-emitting auxiliary layer, the light-emitting layer or the light-emitting auxiliary layer may include a host material, and the host material may include the organic compound. .

In another embodiment of the present invention, the organic light emitting device has one layer selected from the group consisting of a light emitting layer, a light emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a battery blocking layer, and a hole blocking layer. It may further include two or more floors.

One embodiment of the present invention provides a composition for an organic material layer of an organic light-emitting device containing two or more organic compounds represented by Formula 1 above. For example, the organic compound represented by Formula 1 may include a first compound and a second compound. In addition, the organic compound represented by Formula 1 may include a first compound, a second compound, and a third compound, but is not limited to these examples and may include the nth compound (n is an integer of 1 or more. ).

In another embodiment of the present invention, the composition for the organic material layer of the organic light-emitting device may include a first compound represented by Formula 1 and a second compound represented by Formula 1.

In another embodiment of the present invention, the composition for the organic material layer of the organic light-emitting device may include a first compound represented by Formula 1, a second compound represented by Formula 1, and a third compound represented by Formula 1. .

The first compound, second compound, third compound, and nth compound may be organic compounds represented by different chemical formulas (1).

Specific details about the organic compound represented by Formula 1 are the same as described above.

In another embodiment of the present invention, when the organic compound represented by Formula 1 in the composition for the organic material layer of the organic light-emitting device includes a first compound and a second compound, the weight ratio of the first compound and the second compound is 1:10 to 10:1, 1:8 to 8:1, 1:6 to 6:1, 1:4 to 4:1, 1:3 to 3:1, or 1:2 to 2 :1, but is not limited to this.

The composition for the organic material layer of the organic light-emitting device can be used when forming the organic material layer of the organic light-emitting device, and in particular, can be more preferably used when forming the host of the light-emitting layer.

1 to 3 illustrate the stacking order of electrodes and organic material layers of an organic light-emitting device according to an embodiment of the present invention. However, it is not intended that the scope of the present application be limited by these drawings, and structures of organic light-emitting devices known in the art may also be applied to the present application.

According to Figure 1, an organic light emitting device is shown in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, it is not limited to this structure, and an organic light-emitting device may be implemented in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate, as shown in FIG. 2.

Figure 3 illustrates the case where the organic material layer is multi-layered. The organic light emitting device according to FIG. 3 includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of the present application is not limited by this laminated structure, and if necessary, the remaining layers except the light-emitting layer may be omitted, and other necessary functional layers may be added.

In the organic light emitting device according to an embodiment of the present invention, materials other than the organic compound represented by Formula 1 are illustrated below, but these are for illustrative purposes only and are not intended to limit the scope of the present application, and are not intended to limit the scope of the present application. It can be replaced with materials known in the art.

As the anode material, materials with a relatively large work function can be used, and transparent conductive oxides, metals, or conductive polymers can be used. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combination of metal and oxide such as ZnO:Al or SnO ₂ :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline are included, but are not limited to these.

As the cathode material, materials with a relatively low work function can be used, and metals, metal oxides, or conductive polymers can be used. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are, but are not limited to, multi-layered materials such as LiF/Al or LiO ₂ /Al.

As the hole injection layer material, known hole injection layer materials may be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or those described in Advanced Material, 6, p.677 (1994). Described starburst-type amine derivatives, such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4"-tri[phenyl(m-tolyl)amino]triphenylamine ( m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), polyaniline/dodecylbenzenesulfonic acid, a soluble conductive polymer, or Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate), Polyaniline/Camphor sulfonic acid, or Polyaniline/Poly(4-styrene-sulfonate), etc. can be used.

As the hole transport layer material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. may be used, and low molecular or high molecular materials may also be used.

Electron transport layer materials include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, and fluorenone. Derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, etc. may be used, and not only low molecular substances but also high molecular substances may be used.

For example, LiF is typically used as an electron injection layer material in the industry, but the present application is not limited thereto.

Red, green, or blue light-emitting materials can be used as the light-emitting layer material, and if necessary, two or more light-emitting materials can be mixed. At this time, two or more light emitting materials can be deposited and used from individual sources, or they can be premixed and deposited from a single source. Additionally, a fluorescent material may be used as the light-emitting layer material, but it may also be used as a phosphorescent material. The light emitting layer material may be a material that emits light by combining holes and electrons injected from the anode and the cathode respectively, but may also be used as a host material and a dopant material that participates in light emission together.

In one embodiment of the present invention, the organic layer includes the organic compound represented by Chemical Formula 1, and can be used together with a phosphorescent dopant.

As the phosphorescent dopant material, those known in the art can be used. For example, phosphorescent dopant materials represented by LL'MX', LL'L"M, LMX'X", L ₂ MX' and L ₃ M can be used, but the scope of the present invention is not limited by these examples. .

The M may be iridium, platinum, osmium, etc.

L is an anionic bidentate ligand coordinated to M by an sp2 carbon and a hetero atom, and X may function to trap electrons or holes. Non-limiting examples of L, L' and L" include 2-(1-naphthyl)benzoxazole, (2-phenylbenzothiazole), (2-phenylbenzothiazole), (2-phenylbenzothiazole) ), (7,8-benzoquinoline), phenylpyridine, benzothiophenylpyridine, 3-methoxy-2-phenylpyridine, thiophenylpyridine, tolylpyridine, etc. Ratio of X' and X" Limited examples include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, and 8-hydroxyquinolinate.

Specific examples of the phosphorescent dopant are shown below, but are not limited to these examples:

In one embodiment of the present invention, the organic layer includes an organic compound represented by Formula 1, and can be used together with an iridium-based dopant.

In one embodiment of the present invention, (piq) ₂ (Ir) (acac), a red phosphorescent dopant, may be used as the iridium-based dopant.

In one embodiment of the present invention, the content of the dopant may be 1% to 15%, preferably 2% to 10%, more preferably 3% to 7%, based on the total weight of the light emitting layer. .

When using a mixture of hosts of the light emitting layer material, hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, any two or more types of materials, such as an n-type host material or a p-type host material, can be selected and used as the host material of the light-emitting layer.

The organic light emitting device according to an embodiment of the present invention may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.

The organic compound according to an embodiment of the present invention may function in organic electronic devices, including organic solar cells, organic photoreceptors, organic transistors, etc., on a principle similar to that applied to organic light-emitting devices.

Hereinafter, preferred examples are presented to aid understanding of the present invention, but the following examples are provided to facilitate understanding of the present invention and do not limit the present invention thereto.

<Manufacturing example>

Preparation Example 1: Preparation of target compound

1) Preparation of Compound A

1,8-diiodonaphthalene (10.0 g, 26.31 mmol), (3-chloronaphthalen-1-yl)boronic acid (6.2 g) , 30.25 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, PdCl ₂ (dppf) ) (1.0 g, 1.315 mmol) and potassium acetate (KOAc) (10.3 g, 104.95 mmol) were dissolved in dimethyl sulfoxide (DMSO) (100ml) and refluxed at 110°C for 24 hours. did. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extracted at room temperature. Afterwards, moisture was removed from the organic layer using magnesium sulfate (MgSO _-4 ), and then the solvent was removed using a rotary evaporator. The reaction product was purified using silica and then purified by column chromatography (DCM:Hex=1:5) to obtain 5.0 g of Compound A (yield 66.6%).

2) Preparation of compound 104

Compound A (5g, 17.44 mmol), [1,1'-biphenyl]-4-yl(dibenzo[b,d]furan-3-yl)-l2-azane ([1,1'-biphenyl] -4-yl(dibenzo[b,d]furan-3-yl)-l2-azane) (5.83g, 17.44 mmol), tris(dibenzylideneacetone)dipalladium (Pd ₂ (dba) ₃ ) (0.79g , 0.87 mmol), XPhos (0.83 g, 1.744 mmol) and sodium tert-butoxide ( t -BuONa) (5.03g, 52.32 mmol) were added to Xylene (50ml). After dissolving, it was refluxed for 4 hours. After the reaction was completed, the produced solid was filtered, washed with methanol (MeOH), and dried. The dried solid was dissolved in chloroform (CHCl ₃ ), purified into silica, and the solvent was removed using a rotary evaporator. Afterwards, it was recrystallized with acetone to obtain 8.2 g of compound 104 (yield 80.3%).

3) Preparation of compound 67

Compound A (5g, 17.44 mmol), (4-([1,1'-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid ((4-([1,1'-biphenyl]-4 -yl(phenyl)amino)phenyl)boronic acid) (7.64g, 20.93 mmol), tris(dibenzylideneacetone)dipalladium (Pd ₂ (dba) ₃ ) (0.79g, 0.87 mmol), XPhos ( 0.83 g, 1.744 mmol) and sodium hydroxide (NaOH) (2.09 g, 52.32 mmol) in 1,2-dioxane (50 ml) and water (H ₂ O) (10 ml). After adding and dissolving, it was refluxed for 4 hours. After the reaction was completed, the produced solid was filtered, washed with methanol (MeOH), and dried. The dried solid was dissolved in chloroform (CHCl ₃ ), purified into silica, and the solvent was removed using a rotary evaporator. Afterwards, it was recrystallized with acetone to obtain 7.6 g of compound 67 (yield 76.23%).

In Preparation Example 1, instead of compound (a), intermediate compounds (a) of Table 1 below were used, and instead of compounds (b) and (b'), intermediate compounds (b) and (b') of Table 1 below were used. The target compounds shown in Table 1 below were synthesized in the same manner as Preparation Example 1.

compound
number Intermediate compound (a) intermediate compound
(b) or (b') target compound transference number One

50% 12

57% 34

70% 45

65% 66

59% 67

55% 74




66% 80



55% 82



45% 104




59% 110




66% 116




57% 123





62% 125





45% 137



51% 152




55% 161



49% 168



60% 196





47% 216



52% 228



54% 265



65% 280



68%

Preparation Example 2: Preparation of target compound

1) Preparation of compound B-1

1,8-diiodonaphthalene (10.0 g, 26.31 mmol), (4-chloronaphthalen-1-yl)boronic acid (6.2 g) , 30.25 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, PdCl ₂ (dppf) ) (1.0 g, 1.315 mmol) and potassium acetate (KOAc) (10.3 g, 104.95 mmol) were dissolved in dimethyl sulfoxide (DMSO) (100ml) and refluxed at 110°C for 24 hours. did. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extracted at room temperature. Afterwards, moisture was removed from the organic layer using magnesium sulfate (MgSO _-4 ), and then the solvent was removed using a rotary evaporator. The reaction product was purified using silica and then purified by column chromatography (DCM:Hex=1:5) to obtain 5.0 g of compound B-1 (yield 66.6%).

2) Preparation of Compound B

Compound B-1 (5.0 g, 17.44 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxa borolane) (4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane)) (5.31 g, 20.92 mmol), Tris(dibenzylideneacetone)dipalladium (Pd ₂ (dba) ₃ ) (0.79 g, 0.872 mmol), XPhos (0.83 g, 1.74 mmol) and Potassium acetate (KOAc) (5.13 g, 52.32 mmol) was dissolved in 1,4-dioxane (50ml) and refluxed for 5 hours. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extracted at room temperature. Moisture was removed from the organic layer using magnesium sulfate (MgSO _-4 ), and then the solvent was removed using a rotary evaporator. The reaction product was purified using silica and then purified by column chromatography (DCM:Hex=1:6) to obtain 5.9 g of Compound B (yield 89.53%).

3) Preparation of compound 284

Compound B (5.9 g, 15.59 mmol), 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (2,4-di( [1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine) (6.55 g, 15.59 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) (0.9 g, 0.78 mmol) and potassium carbonate (K ₂ CO ₃ ) (6.46 g, 46.77 mmol) with 1,4-dioxane (60ml) and water (H ₂ O ) (12ml), dissolved, and refluxed for 2 hours. After the reaction was completed, the produced solid was filtered, washed with methanol (MeOH), and dried. The dried solid was dissolved in chloroform (CHCl ₃ ), purified into silica, and the solvent was removed using a rotary evaporator. Afterwards, 6.6 g of compound 284 was obtained by recrystallization with acetone (yield 66.66%).

In Preparation Example 2, the same method as Preparation Example 2 was used, instead of compound (c), intermediate compound (c) of Table 2 below was used, and instead of compound (d), intermediate compound (d) of Table 2 below was used. The target compounds shown in Table 2 below were synthesized.

compound
number Intermediate compounds (c) Intermediate compound (d) target compound transference number 284



79% 302


57% 339


70% 362


65% 374


59% 394

61% 395
66% 404

62% 412

77% 418

59% 439
66% 443
60% 451
71% 457
76% 499


53% 523
60% 597


63%

Preparation Example 3: Preparation of target compound

1) Preparation of compound C-2

1,8-diiodonaphthalene (10.0 g, 26.31 mmol), (6-chloronaphthalen-1-yl)boronic acid (6.2 g) , 30.25 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, PdCl ₂ (dppf) ) (1.0 g, 1.315 mmol) and potassium acetate (KOAc) (10.3 g, 104.95 mmol) were dissolved in dimethyl sulfoxide (DMSO) (100ml) and refluxed at 110°C for 24 hours. did. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extracted at room temperature. Afterwards, moisture was removed from the organic layer using magnesium sulfate (MgSO _-4 ), and then the solvent was removed using a rotary evaporator. The reaction product was purified using silica and then purified by column chromatography (DCM:Hex=1:5) to obtain 5.0 g of compound C-2 (yield 66.6%).

2) Preparation of compound C-1

Compound C-2 (5.0 g, 17.44 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxa borolane) (4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane)) (5.31 g, 20.92 mmol), Tris(dibenzylideneacetone)dipalladium (Pd ₂ (dba) ₃ ) (0.79 g, 0.872 mmol), XPhos (0.83 g, 1.74 mmol) and Potassium acetate (KOAc) (5.13 g, 52.32 mmol) was dissolved in 1,4-dioxane (50ml) and refluxed for 5 hours. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extracted at room temperature. Moisture was removed from the organic layer using magnesium sulfate (MgSO _-4 ), and then the solvent was removed using a rotary evaporator. The reaction product was silica purified, and the reaction product was purified by column chromatography (DCM:Hex=1:6) to obtain 5.9 g of compound C-1 (yield 89.53%).

3) Preparation of Compound C

Compound C-1 (5.9 g, 15.59 mmol), 2,4-dichloroquinazoline (3.1 g, 15.59 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) (0.9 g, 0.78 mmol) and potassium carbonate (K ₂ CO ₃ ) (6.46 g, 46.77 mmol) with 1,4-dioxane (60ml) and water (H ₂ O ) (12ml), dissolved, and refluxed for 2 hours. After the reaction was completed, the produced solid was filtered, washed with methanol (MeOH), and dried. The dried solid was dissolved in chloroform (CHCl ₃ ), purified into silica, and the solvent was removed using a rotary evaporator. Afterwards, 5.7 g of Compound C was obtained by recrystallization with acetone (yield 86.36%).

4) Preparation of compound 425

Compound C (5.7 g, 13.74 mmol), 5H-benzo[b]carbazole (3.28 g, 15.11 mmol) and cesium carbonate (Cs ₂ CO ₃ ) (11.19 g, 34.35 mmol) was dissolved in dimethylacetamide (DMA) (60ml) and refluxed at 160°C for 4 hours. After the reaction was completed, the produced solid was filtered, washed with methanol (MeOH), and dried. The dried solid was dissolved in chloroform (CHCl ₃ ), purified into silica, and the solvent was removed using a rotary evaporator. Afterwards, 6.1 g of compound 425 was obtained by recrystallization with acetone (yield 74.57%).

In Preparation Example 3, instead of compound (e), intermediate compound (e) of Table 3 below was used, instead of compound (f), intermediate compound (f) of Table 3 below was used, and instead of compound (g), Using the intermediate compound (g) in Table 3 below, the target compounds in Table 3 below were synthesized in the same manner as Preparation Example 3.

compound number Intermediate compound (e) Intermediate compounds (f) Intermediate compounds (g) target compound transference number 354

64% 425

57% 483

55% 547

65% 600


59%

The remaining compounds other than those described in Preparation Examples 1 to 3 and Tables 1 to 3 were also prepared in the same manner as described in the Preparation Examples above, and the synthesis results are shown in Tables 4 and 5 below. Table 4 below shows the measured values of ¹ H NMR (CDCl ₃ , 200Mz), and Table 5 below shows the measured values of Field desorption mass spectrometry (FD-MS).

NO ^One H NMR (CDCl ₃ , 300Mz) One 8.95 (d, 1H), 8.45 (d, 1H), 8.42 (d, 2H), 8.10 (t, 2H), 7.65-7.37 (m, 21H), 7.27 (t, 2H), 7.24 (t, 2H) , 7.11-7.00 (m, 4H) 12 9.02 (dd, 1H), 8.95 (dd, 1H), 7.80 (dd, 2H), 7.55 (m, 4H), 7.41 (t, 1H), 7.37 (s, 1H), 7.35 (t, 1H), 7.27 (d, 2H), 7.07-7.06 (m, 8H) 34 9.02 (dd, 1H), 8.95 (dd, 1H),8.03 (s, 1H), 7.80 (d, 2H), 7.75 (d, 2H), 7.69 (d, 2H), 7.57-7.24 (m, 18H) , 7.08 (d, 2H), 7.00 (t, 1H), 6.91 (s, 1H) 45 8.97 (s, 1H), 8.22 (s, 1H), 7.90-7.80 (m, 4H), 7.69 (d, 2H), 7.55-7.16 (m, 12H), 7.08 (d, 2H), 7.00 (s, 1H) 66 8.32 (s, 1H), 7.85 (s, 1H), 7.80 (s, 2H), 7.79-7.38 (m, 22H), 7.27 (d, 4H), 7.11 (s, 1H) 67 8.32 (s, 1H), 7.85-7.69 (m, 8H), 7.55-7.41 (m, 11H), 7.27-7.24 (m, 6H), 7.08-7.00 (m, 3H) 74 8.32 (s, 1H), 8.10 (s, 1H), 7.85-7.75 (m, 8H), 7.55-25 (m, 24H), 7.14 (s, 1H), 7.08 (s, 2H) 80 8.32 (s, 1H), 8.03 (s, 1H), 7.98 (d, 1H), 7.85-7.69 (m, 8H), 7.55-7.27 (m, 19H), 6.91 (d, 1H) 82 8.45 (d, 1H), 8.32 (s, 1H), 7.86-7.64 (m, 11H), 7.55-7.43 (m, 13H), 7.31-7.27 (m, 5H) 104 8.22 (s, 1H), 7.98 (d, 1H), 7.80-7.55 (m, 7H), 7.54-7.24 (m, 16H), 7.11 (s, 1H), 6.97 (d, 1H) 110 7.80 (d, 1H)m 7.75 (d, 2H), 7.71 (d, 1H), 7.69 (s, 2H), 7.62 (d, 1H), 7.55-7.24 (m, 18H), 7.11 (s, 2H) 116 8.10 (d, 1H), 7.80-7.66 (m, 7H), 7.56-7.14(m, 19H), 7.08 (d, 1H) 123 8.91 (d, 1H), 8.50 (d, 1H), 7.82-7.38 (m, 24H), 7.27 (d, 4H), 7.11 (s, 1H) 125 8.91 (d, 1H), 8.50 (d, 1H), 7.82-7.69 (m, 10H), 7.55-7.41 (m, 14H), 7.27 (m, 5H), 7.18 (d, 1H), 7.17 (d, 1H) 137 8.95 (d, 1H), 8.91 (d, 1H), 8.50 (d, 1H), 8.27 (d, 1H), 7.82-7.69 (m, 8H), 7.55-7.24 (m, 16H), 7.08 (d, 2H), 7.00 (t, 1H) 152 8.91 (d, 1H), 8.50 (d, 1H), 8.20 (s, 1H), 8.13 (s, 1H), 7.98 (d, 1H), 7.82-7.24 (m, 20H), 7.08 (d, 2H) , 7.00 (t, 1H) 161 8.63 (d, 1H), 7.90 (d, 1H), 7.86 (d, 1H), 7.80 (d, 2H), 7.75 (d, 2H), 7.69 (d, 2H), 7.63 (d, 1H), 7.55 -7.27 (m, 17H), 7.15 (d, 1H) 168 8.63 (d, 1H), 7.94 (d, 1H), 7.80 (d, 2H), 7.75 (d, 6H), 7.69 (d, 2H), 7.63 (t, 1H), 7.55-7.41 (m, 12H) , 7.27 (d, 4H) 196 8.04 (d, 1H), 7.84 (d, 1H), 7.80 (d, 2H), 7.75 (d, 2H), 7.72 (d, 1H), 7.69 (d, 2H), 7.55-7.08 (m, 22H) 216 8.04 (d, 1H), 7.96 (d, 1H), 7.80 (d, 2H), 7.74 (d, 1H), 7.72 (d, 1H), 7.69 (d, 2H), 7.67 (d, 1H), 7.64 (s, 1H), 7.55-7.43 (m, 7H), 7.24 (t, 4H), 7.08-7.00 (m, 6H) 228 8.45 (d, 1H), 7.95 (s, 1H), 7.86 (d, 1H), 7.85 (d, 1H), 7.80 (d, 2H), 7.75 (d, 2H), 7.69 (d, 2H), 7.56 -7.41 (m, 11H), 7.31 (t, 1H), 7.27 (d, 2H), 7.17 (d, 1H), 7.16 (d, 1H), 7.11 (s, 1H) 241 8.54 (d, 1H), 8.19 (d, 1H), 7.99 (d, 2H), 7.90-7.41 (m, 15H), 7.27-7.17 (m, 7H), 7.08 (d, 2H), 7.00 (t, 1H) 265 8.10 (d, 1H), 7.80 (d, 2H), 7.75 (d, 2H), 7.69 (d, 2H), 7.55-7.24 (m, 18H), 7.14 (t, 1H), 7.11 (s, 1H) , 7.08 (d, 1H) 284 8.97 (dd, 2H), 8.25 (d, 4H), 7.82 (s, 1H), 7.80 (d, 2H), 7.75 (d, 4H), 7.69 (d, 2H), 7.55-7.41 (m, 10H) , 7.25 (d, 4H) 302 8.97 (d, 2H), 8.30 (d, 4H), 8.23 (s, 1H), 7.85 (d, 4H), 7.82 (s, 1H), 7.80 (d, 2H), 7.75 (d, 4H), 7.69 (d, 2H), 7.55 (t, 2H), 7.49 (t, 4H), 7.48 (t, 2H), 7.41 (t, 2H) 339 9.02 (d, 1H) 8.95 (d, 1H), 8.36 (d, 4H), 8.25 (d, 2H), 7.80 (d, 2H), 7.69 (d, 2H), 7.55 (t, 2H), 7.50 ( m, 6H), 7.41 (t, 1H), 7.37 (s, 1H), 7.35 (t, 1H), 7.25 (dd, 6H) 354 8.97 (d, 2H), 8.55 (d, 1H), 8.13 (d, 1H), 7.98 (d, 1H), 7.84-7.80 (m, 5H), 7.69 (d, 2H), 7.59-7.31 (m, 10H), 7.16 (t, 1H), 7.13 (d, 1H), 7.11 (t, 1H) 362 8.46 (s, 1H), 8.36 (d, 2H), 8.25 (d, 2H), 8.09 (d, 1H), 8.06 (d, 1H), 7.99 (d, 1H), 7.81 (d, 1H), 7.80 (d, 2H), 7.79 (d, 1H), 7.69-7.50 (m, 12H), 7.38 (d, 1H), 7.25 (d, 2H) 374 8.46 (s, 1H), 8.36 (d, 2H), 7.98 (d, 1H), 7.81-7.69 (m, 8H), 7.57-7.50 (m, 9H), 7.39 (t, 1H), 7.31 (t, 1H) 394 8.54 (d, 1H), 8.46(s, 1H), 7.99 (d, 1H), 7.84 (d, 2H), 7.81-7.80 (m, 4H), 7.69-7.49 (m, 12H), 7.29 (d, 1H) 395 9.09 (s, 1H), 8,49 (d, 1H), 8.46 (s, 1H), 8.16 (d, 1H), 8.08 (s, 1H), 8.00 (s, 1H), 7.98 (d, 1H) , 7.81-7.79 (d, 4H), 7.69-7.39 (m, 14H) 404 8.36 (d, 2H), 8.32 (s, 1H), 8.25 (d, 4H), 8.09 (d, 1H), 8.06 (d, 1H), 7.99 (d, 1H), 7.85-7.79 (d, 4H) , 7.69-7.50 (m, 12H), 7.38 (d, 1H), 7.25 (d, 4H) 412 9.02 (d, 1H), 8.95 (d, 1H), 8.36 (d, 4H), 7.85-7.78 (d, 5H), 7.69 (d, 2H), 7.56-7.35 (m, 13H) 418 8.36 (d, 4H), 8.32 (s, 1H), 7.85-7.79 (d, 4H), 7.78 (d, 1H), 7.76 (s, 1H), 7.69 (d, 2H), 7.60-7.50 (m, 14H) 425 8.55 (d, 1H), 8.46 (s, 1H), 8.28 (d, 1H), 8.13 (d, 1H), 7.84-7.69 (m, 10H), 7.58-7.51 (m, 8H), 7.16 (t, 1H), 7.11 (t, 1H) 439 9.09 (s, 2H), 9.07 (d, 1H), 8.49 (d, 2H), 8.16 (d, 2H), 8.08 (s, 2H), 8.00 (d, 3H), 7.84 (d, 1H), 7.82 (d, 1H), 7.80 (d, 2H), 7.69-7.48 (m, 9H) 443 9.07 (d, 1H), 8.04 (d, 4H), 8.00 (t, 1H), 7.84 (d, 1H), 7.82 (d, 1H), 7.80 (d, 2H, 7.69 (d, 2H, 7.55 (t) , 2H), 7.48 (d, 1H), 7.31 (d, 4H) 451 9.07 (d, 1H), 8.30 (d, 2H), 8.13 (d, 1H), 8.00 (t, 1H), 7.85-7.69 (m, 12H), 7.58-7.41 (m, 7H) 457 9.07 (d, 1H), 8.00 (t, 1H), 7.86 (d, 1H), 7.84 (d, 3H), 7.82 (d, 1H), 7.80 (d, 2H), 7.78 (d, 1H), 7.69 (d, 2H), 7.55-7.48 (m, 6H), 7.33 (t, 1H), 7.31 (t, 1H) 483 9.07 (d, 1H), 8.42 (d, 2H), 8.19 (d, 1H), 8.13 (d, 1H), 8.10 (t, 2H), 8.00 (t, 1H), 7.84-7.80 (m, 7H) , 7.69 (d, 2H), 7.58-7.40 (m, 8H), 7.16 (d, 1H), 7.05 (t, 1H) 499 9.09 (s, 1H), 8.55 (d, 1H), 8.49 (d, 1H), 8.36 (d, 2H), 7.98 (d, 1H), 7.89 (s, 1H), 7.80-7.43 (m, 19H) , 7.16 (t, 1H), 7.11 (t, 1H) 523 8.49 (d, 1H), 8.46 (s, 1H), 8.30 (d, 2H), 7.93-7.69 (d, 12H), 7.55-7.31 (m, 8H) 547 9.02 (s, 1H), 8.55 (d, 1H), 8.54 (d, 1H), 8.28 (d, 1H), 7.97 (d, 1H), 7.84-7.67 (m, 11H), 7.55-7.43 (m, 7H), 7.16 (t, 1H), 7.11 (t, 1H)

compound FD-MS compound FD-MS 12 m/z=495.63 (C ₃₈ H ₂₅ N=495.20) 12 m/z= 531.61 (C ₃₈ H ₂₃ F ₂ N =531.18) 34 m/z=661.80 (C ₅₀ H ₃₁ NO=661.24) 45 m/z=535.69 (C ₄₁ H ₂₉ N=535.23) 66 m/z=621.78 (C ₄₈ H ₃₁ N=621.25) 67 m/z=571.72 (C ₄₄ H ₂₉ N=571.23) 74 m/z=723.92 (C ₅₆ H ₃₇ N=723.29) 80 m/z=661.80 (C ₅₀ H ₃₁ NO=661.24) 82 m/z=677.87 (C ₅₀ H ₃₁ NS=677.22) 104 m/z=585.71 (C ₄₄ H ₂₇ NO=585.21) 110 m/z=545.69 (C ₄₂ H ₂₇ N=545.21) 116 m/z=571.72 (C ₄₄ H ₂₉ N=571.23) 123 m/z=621.78 (C ₄₈ H ₃₁ N=621.25) 125 m/z=647.82 (C ₅₀ H ₃₃ N=647.26) 137 m/z=621.78 (C ₄₈ H ₃₁ N=621.25) 152 m/z=635.77 (C ₄₈ H ₂₉ NO=635.22) 161 m/z=611.79 (C ₄₁ H ₃₃ N=611.26) 168 m/z=571.72 (C ₄₄ H ₂₉ N=571.23) 196 m/z=621.78 (C ₄₈ H ₃₁ N=621.25) 216 m/z=601.77 (C ₄₄ H ₂₇ NS=601.19) 228 m/z=601.77 (C ₄₄ H ₂₇ NS=601.19) 241 m/z=571.72 (C ₄₄ H ₂₉ N=571.23) 265 m/z=571.72 (C ₄₄ H ₂₉ N=571.23) 280 m/z=589.83 (C ₄₄ H ₁₁ D ₁₈ N=589.34) 284 m/z=635.77 (C ₄₇ H ₂₉ N ₃ =635.24) 302 m/z=634.78 (C ₄₈ H ₃₀ N ₂ =634.24) 339 m/z=635.77 (C ₄₇ H ₂₉ N ₃ =635.24) 354 m/z=635.73 (C ₄₆ H ₂₅ N ₃ O=635.20) 362 m/z=609.73 (C ₄₅ H ₂₇ N ₃ =609.22) 374 m/z= 573.66 (C ₄₁ H ₂₃ N ₃ O=573.18) 394 m/z= 546.63 (C ₄₀ H ₂₂ N ₂ O=546.17) 395 m/z=623.72 (C ₄₅ H ₂₅ N ₃ O=623.20) 404 m/z=685.83 (C ₅₁ H ₃₁ N ₃ =685.25) 412 m/z=609.73 (C ₄₅ H ₂₇ N ₃ =609.22) 418 m/z=649.75 (C ₄₇ H ₂₇ N ₃ O=649.22) 425 m/z= 595.71 (C ₄₄ H ₂₅ N ₃ =595.20) 439 m/z= 583.69 (C ₄₃ H ₂₅ N ₃ =583.20) 443 m/z= 519.55 (C ₃₅ H ₁₉ F ₂ N ₃ =519.15) 451 m/z= 532.65 (C ₄₀ H ₂₄ N ₂ =532.19) 457 m/z=512.63 (C ₃₆ H ₂₀ N ₂ S=512.13) 483 m/z=669.79 (C ₅₀ H ₂₇ N ₃ =669.22) 499 m/z=648.77 (C ₄₇ H ₂₈ N ₄ =648.23) 523 m/z=588.73 (C ₄₂ H ₂₄ N ₂ S=588.17) 547 m/z= 595.71 (C ₄₄ H ₂₅ N ₃ =595.20) 597 m/z=625.83 (C ₄₅ H ₁₁ D ₁₆ N ₃ =625.32) 600 m/z=605.77 (C ₄₄ H ₁₅ D ₁₀ N ₃ =605.27)

<Experimental example>

Experimental Example 1

(1) Manufacturing of organic light emitting devices

A glass substrate coated with a thin film of 115 Å thick indium tin oxide (ITO), 100 Å thick silver (Ag), and 15 Å thick indium tin oxide (ITO) was washed with distilled water ultrasonic waves. . After washing with distilled water, ultrasonic cleaning was performed with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UV (Ultraviolet ozone) for 5 minutes using UV light in a UV (Ultraviolet) cleaner. Afterwards, the substrate was transferred to a plasma cleaner (PT), then plasma treated in a vacuum to increase the ITO work function and remove the remaining film, and then transferred to a thermal evaporation equipment for organic deposition.

1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile (1,4,5,8,9,11) with a thickness of 100Å was used as a hole injection layer, which is a common layer on the ITO electrode (anode). -hexaazatriphenylenehexacarbonitrile: HAT-CN), N,N'-di-[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl)-4 with a thickness of 1100Å as a hole transport layer, 4'-diamine (N,N'-di-[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl)-4,4'-diamine:α-NPB), light auxiliary layer N,N'-bis(3-methylphenyl)-N,N'-diphenylbenzidine (TPD) with a thickness of 800 Å and As an electron blocking layer, 150 Å thick di-[4-(N,N-di-p-tolyl-amino)-phenyl]cyclohexane (di-[4-(N,N-di-p-tolyl-amino)- [phenyl]cyclohexane: TAPC)) was deposited.

After forming the hole injection layer, hole transport layer, light auxiliary layer, and electron blocking layer in this way, a light emitting layer was thermally vacuum deposited thereon as follows. The light-emitting layer was deposited with a single compound listed in Table 6 below as a red host, or two types of compounds listed in Table 7 below to a thickness of 400 Å through one source, and (piq) ₂ (Ir)(acac) as a red phosphorescent dopant. (piq) ₂ (Ir)(acac) was doped and deposited on the host in an amount of 3 wt% of the deposition thickness of the light emitting layer.

Afterwards, Bathophenanthroline (Bphen) was deposited to a thickness of 30Å as a hole blocking layer, and TPBI was deposited to a thickness of 250Å as an electron transport layer on top of it.

Finally, lithium fluoride (LiF) was deposited to a thickness of 10Å on the electron transport layer to form an electron injection layer, and then a silver (Ag) cathode was deposited to a thickness of 200Å to form the cathode on the electron injection layer, thereby forming an organic A light emitting device was manufactured.

Meanwhile, all organic compounds required for the production of organic light-emitting devices were purified by vacuum sublimation under 10 ^-8 to 10 ^-6 torr for each material and used in the production of organic light-emitting devices.

(2) Driving voltage and luminous efficiency of organic electroluminescent devices

The electroluminescence (EL) characteristics of the organic light emitting device manufactured as described above were measured using McScience's M7000, and the standard luminance was measured to be 6,000 cd/ through the lifespan measurement equipment (M6000) manufactured by McScience using the measurement results. When m ² , the lifetime T ₉₅ (unit: h, time), which is the time for 95% of the initial luminance, was measured.

The results of measuring the driving voltage, luminous efficiency, and lifespan of the organic light-emitting device manufactured according to the present invention are shown in Table 6 below.

compound driving voltage
(V) Luminous efficiency
(cd/A) Color coordinates
(x, y) life span
(T ₉₅ ) Comparative Example 1 A 4.55 7.0 (0.682, 0.317) 28 Comparative Example 2 B 4.47. 7.2 (0.691, 0.309) 33 Comparative Example 3 C 4.39 9.9 (0.675, 0.325) 35 Comparative Example 4 D 4.57 12.5 (0.681, 0.319) 40 Comparative Example 5 E 4.53 14.6 (0.675, 0.325) 41 Comparative Example 6 F 4.60 4.7 (0.684, 0.316) 22 Comparative Example 7 G 4.66 5.0 (0.669, 0.321) 20 Example 1 One 3.80 26.1 (0.682, 0.317) 74 Example 2 12 3.77 26.3 (0.675, 0.325) 80 Example 3 34 3.82 25.7 (0.682, 0.317) 70 Example 4 45 3.84 24.9 (0.691, 0.309) 67 Example 5 66 3.64 33.1 (0.691, 0.309) 92 Example 6 67 3.66 32.0 (0.675, 0.325) 96 Example 7 74 3.65 32.8 (0.681, 0.319) 98 Example 8 80 3.58 34.8 (0.682, 0.317) 103 Example 9 82 3.62 33.4 (0.675, 0.325) 94 Example 10 104 3.71 29.8 (0.669, 0.321) 86 Example 11 110 3.74 28.7 (0.681, 0.319) 80 Example 12 116 3.75 28.3 (0.691, 0.309) 77 Example 13 123 3.62 31.5 (0.681, 0.319) 88 Example 14 125 3.64 32.0 (0.678, 0.322) 90 Example 15 137 3.75 27.7 (0.691, 0.309) 84 Example 16 152 3.78 26.6 (0.675, 0.325) 80 Example 17 161 3.76 29.8 (0.681, 0.319) 81 Example 18 168 3.79 27.0 (0.684, 0.316) 79 Example 19 196 3.80 26.8 (0.669, 0.321) 72 Example 20 216 3.77 27.1 (0.682, 0.317) 75 Example 21 228 3.79 27.3 (0.691, 0.309) 77 Example 22 265 3.84 25.4 (0.675, 0.325) 73 Example 23 280 3.60 34.9 (0.681, 0.319) 120 Example 24 284 3.88 20.3 (0.681, 0.319) 60 Example 25 374 3.84 22.1 (0.682, 0.317) 65 Example 26 418 3.79 24.6 (0.682, 0.317) 58 Example 27 451 3.85 21.9 (0.675, 0.325) 68 Example 28 457 3.90 20.8 (0.691, 0.309) 52 Example 29 499 3.65 26.8 (0.675, 0.325) 66 Example 30 597 3.82 23.0 (0.678, 0.322) 70 Example 31 547 3.60 28.6 (0.681, 0.319) 85 Example 32 600 3.59 29.1 (0.691, 0.309) 95

Table 6 above is an example of applying a single host material, in which a compound with good hole transport ability among the condensed polycyclic compounds according to the present invention is used as the first host (donor (p-Host)), and the present invention is used as the second host. This is an example of depositing two host compounds with one source, using a compound with good electron transport ability among the condensed polycyclic compounds according to this as an acceptor (n-Host).

The compounds of Comparative Examples 1 to 7 are the same as Comparative Compounds A to G below:

From the results in Table 6, it was confirmed that the organic light-emitting device containing the compound of the present invention had a lower driving voltage and that the luminous efficiency and lifespan were significantly improved compared to the organic light-emitting device containing the compounds of Comparative Examples 1 to 7.

The skeleton of benzofluoranthene, the parent nucleus of the compound of the present invention, is more robust and has higher thermal stability than the skeleton of the mother nucleus of comparative compounds A to F. In addition, the compound of Formula 1 of the present invention can substitute substituents at various positions and easily adjust the molecular weight by expanding aromaticity, so that a variety of host materials with an appropriate band gap can be manufactured.

The comparative compound G has a benzofluoranthene group similar to the parent nucleus of the compound of formula 1 of the present invention, but has a structure in which a carbazole derivative is directly bonded to the skeleton, whereas the compound of formula 1 of the present invention contains quinazoline as a linker. It is the structure of a bipolar compound bound to an acceptor with good electron transport ability, such as quinazoline or quinoxaline. This further increases the balance effect with the acceptor, forming an appropriate HOMO level, resulting in high luminous efficiency and long lifespan.

The results of measuring the driving voltage, luminous efficiency, and lifespan of the organic light-emitting device manufactured according to the present invention are shown in Table 7 below.

first host
(P) second host
(N) weight
ratio
(P:N) driving voltage
(V) Luminous efficiency
(cd/A) Color coordinates
(x, y) life span
(T ₉₅ ) Comparative Example 8 D B 1:1 3.86 20.4 (0.669, 0.321) 90 Comparative Example 9 D 451 1:1 3.67 29.9 (0.669, 0.321) 166 Example 33 67 395 1:1 3.35 54.6 (0.683, 0.317) 220 Example 34 80 284 1:1 3.36 54.8 (0.681, 0.319) 214 Example 35 228 395 1:2 3.42 49.8 (0.678, 0.322) 196 Example 36 34 302 1:2 3.44 48.7 (0.685, 0.315) 188 Example 37 152 302 1:2 3.40 49.0 (0.668, 0.351) 192 Example 38 12 339 1:3 3.50 37.7 (0.681, 0.319) 199 Example 39 168 404 1:3 3.49 40.0 (0.691, 0.309) 186 Example 40 216 374 1:3 3,52 42.2 (0.675, 0.325) 189 Example 41 74 374 1:3 3.38 53.8 (0.684, 0.316) 216 Example 42 137 443 1:2 3.46 45.9 (0.682, 0.317) 210 Example 43 137 439 1:2 3.44 46.7 (0.675, 0.325) 197 Example 44 80 362 1:2 3.40 50.0 (0.682, 0.317) 208 Example 45 66 499 1:1 3.51 36.6 (0.691, 0.309) 185 Example 46 168 499 1:1 3.54 34.7 (0.681, 0.319) 180 Example 47 One 523 1:1 3.48 44.6 (0.682, 0.317) 183 Comparative Example 48 G 412 1:2 3.70 29.8 (0.681, 0.319) 120 Comparative Example 49 483 C 1:1 3.60 34.7 (0.675, 0.325) 159 Example 50 425 412 1:2 3.38 52.7 (0.684, 0.316) 216 Example 51 547 451 1:1 3.40 52.2 (0.691, 0,309) 209

From the results in Table 7, when the compound represented by Formula 1 of the present invention is included in the organic material layer of an organic light-emitting device by combining two types of hosts as an N-type host and a P-type host, the organic It was confirmed that the driving voltage, luminous efficiency, and lifespan of the light emitting device were improved. From this, it can be expected that an exciplex phenomenon will occur when two types of compounds are mixed and deposited.

The exciplex phenomenon is a phenomenon in which energy equivalent to the HOMO energy level of a strong donor (p-host) and the LUMO energy level of a strong acceptor (n-host) are released through electron exchange between two molecules. When an exciplex phenomenon occurs between two molecules, reverse intersystem crossing (RISC) occurs, which can increase the internal quantum efficiency of fluorescence up to 100%. When a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport ability are used as hosts for the emitting layer, holes are injected into the p-host and electrons are injected into the n-host. Because it is injected, the driving voltage can be lowered, which can help improve lifespan. When the exciplex phenomenon occurs, a new S1 (singlet state) energy level and T1 (triplet state) energy level are formed, and a change in photoluminescence (PL) that is red shifted from that of each molecule can be confirmed. there is.

In particular, the compound represented by Formula 1 is used as a P-type host compound, and the compound represented by Formula 1, which has good electron transport ability, is used as an N-type host compound (acceptor, acceptor(n-Host)). Upon injection, a red-shifted photoluminescence (PL) change can be observed, forming an exciplex, which can help improve luminescence characteristics. In addition, it was confirmed that the lifespan was significantly improved due to appropriate movement of the light-emitting zone in the light-emitting layer as the N-type host compound (acceptor (n-Host)) of the compound represented by Formula 1, which has good electron transport ability, was injected. .

Claims (11)

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

In Formula 1,
R1 to R12 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; A group represented by the following formula 1-1; And it is selected from the group consisting of a group represented by the following formula 1-2,
At least one of R1 to R12 is a group represented by Formula 1-1; or a group represented by Formula 1-2;
[Formula 1-1]

In Formula 1-1,
R21 and R22 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group of C6 to C60; and a substituted or unsubstituted C2 to C60 heteroaryl group,
L1 is a single bond; Substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group;
m is an integer from 0 to 5, and when m is 2 or more, L1 is the same as or different from each other,
[Formula 1-2]

In Formula 1-2,
X1 is N or CRa,
X2 is N or CRb,
X3 is N or CRc,
X4 is N or CRd,
X5 is N or CRe,
At least one of X1 to X5 is N,
Ra to Re are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group, or a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring where two or more adjacent groups are bonded to each other; Or a substituted or unsubstituted C2 to C60 hetero ring;
L2 is a single bond; Substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group;
n is an integer from 0 to 5, and when n is 2 or more, L2 are the same or different from each other. delete According to paragraph 1,
An organic compound in which the group represented by Formula 1-2 is any one of the following Formulas 1-2-a to 1-2-d:
[Formula 1-2-a]

[Formula 1-2-b]

[Formula 1-2-c]

[Formula 1-2-d]

In Formulas 1-2-a to 1-2-d,
L2, X1 to X5 and n are as defined in Formula 1-2 above,
X6 and X7 are C, O or S,
a is 0 or 1, and when a is 1, it forms a T1 ring or a T2 ring,
The T1 ring and the T2 ring are the same or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aromatic ring; Or a substituted or unsubstituted C2 to C60 heteroaromatic ring,
R31 to R35 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Or a substituted or unsubstituted C1 to C60 alkoxy group; A substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group, or a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring where two or more adjacent groups are bonded to each other; Or a substituted or unsubstituted C2 to C60 hetero ring;
p is an integer from 0 to 4,
q is an integer from 0 to 3,
When a is 0, r is an integer from 0 to 4, and when a is 1, r is an integer from 0 to 3. According to paragraph 1,
The organic compound represented by Formula 1 does not contain deuterium as a substituent, or has a deuterium content of 1% to 100% based on the total number of hydrogen atoms and deuterium atoms. According to paragraph 1,
The organic compound represented by Formula 1 is any one selected from the group consisting of the following compounds:





























. first electrode;
a second electrode provided opposite to the first electrode; and
An organic light-emitting device comprising: one or more organic material layers provided between the first electrode and the second electrode,
The organic material layer is an organic light-emitting device comprising the organic compound according to any one of claims 1 and 3 to 5. According to clause 6,
An organic light-emitting device wherein the organic layer includes a light-emitting layer or a light-emitting auxiliary layer, and the light-emitting layer or a light-emitting auxiliary layer includes the organic compound. According to clause 6,
The organic material layer includes a light-emitting layer or a light-emitting auxiliary layer, the light-emitting layer or a light-emitting auxiliary layer includes a host material, and the host material includes the organic compound. According to clause 6,
The organic light-emitting device further includes one or two layers selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a battery blocking layer, and a hole blocking layer. , organic light emitting device. A composition for an organic material layer of an organic light-emitting device, comprising two or more organic compounds represented by Formula 1 according to any one of claims 1 and 3 to 5. According to clause 10,
The composition for the organic material layer of the organic light-emitting device includes a first compound represented by Formula 1 and a second compound represented by Formula 1, and the weight ratio of the first compound and the second compound is 1:10 to 10:1. A composition for the organic material layer of an organic light-emitting device.