KR20220021799A - Heterocyclic compound, organic light emitting device comprising same, manufacturing method of same and composition for organic layer of organic light emitting device - Google Patents

Abstract

The present specification relates to a heterocyclic compound represented by chemical formula 1, an organic light emitting device including the same, a method for manufacturing the same, and a composition for an organic material layer. A compound described herein can be used as the organic material layer of the organic light emitting device. The compound can serve as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and the like in the organic light emitting device.

Description

Heterocyclic compound, organic light emitting device including same, manufacturing method thereof, and composition for organic material layer

The present specification relates to a heterocyclic compound, an organic light emitting device including the same, a method for manufacturing the same, and a composition for an organic material layer.

The organic electroluminescent device is a kind of self-emission type display device, and has a wide viewing angle, excellent contrast, and fast response speed.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form a pair, and then disappear and emit light. The organic thin film may be composed of a single layer or multiple layers, if necessary.

The material of the organic thin film may have a light emitting function if necessary. For example, as the organic thin film material, a compound capable of forming the light emitting layer by itself may be used, or a compound capable of serving as a host or dopant of the host-dopant light emitting layer may be used. In addition, as a material of the organic thin film, a compound capable of performing the roles of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, and the like may be used.

In order to improve the performance, lifespan, or efficiency of an organic light emitting diode, the development of a material for an organic thin film is continuously required.

U.S. Patent No. 4,356,429

An object of the present invention is to provide a heterocyclic compound, an organic light emitting device including the same, a method for manufacturing the same, and a composition for an organic material layer.

In an exemplary embodiment of the present application, a heterocyclic compound represented by the following Chemical Formula 1 is provided.

[Formula 1]

In Formula 1,

N-Het is a substituted or unsubstituted, monocyclic or polycyclic C2 to C60 heterocyclic group containing one or more N,

L1 to L3 are the same as or different from each other and each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group,

Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R201R202; And -NR201R202, or two or more groups adjacent to each other combine with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle,

m, c and p are integers from 0 to 4;

n and d are integers from 1 to 6,

a and b are integers from 0 to 3,

wherein R201 and R202 are a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group.

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

In addition, an exemplary embodiment of the present application provides an organic light emitting device in which the organic material layer including the heterocyclic compound of Formula 1 further includes a heterocyclic compound represented by the following Chemical Formula 2.

[Formula 2]

In Formula 2,

Rc and Rd are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiR10R11R12; -P(=O)R10R11; And -NR10R11, or two or more groups adjacent to each other combine with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle,

R10, R11, and R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

Ra and Rb are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

r and s are integers from 0 to 7.

In addition, another exemplary embodiment of the present application provides a composition for an organic material layer of an organic light emitting device comprising the heterocyclic compound represented by Formula 1, and the heterocyclic compound represented by Formula 2 above.

Finally, an exemplary embodiment of the present application includes the steps of preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layer, wherein the forming of the organic material layer comprises forming one or more organic material layers using the composition for an organic material layer according to an exemplary embodiment of the present application. A method of manufacturing an organic light emitting device is provided.

The compound described herein can be used as an organic material layer of an organic light emitting device. The compound may serve as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. in the organic light emitting device. In particular, the compound may be used as a material for a light emitting layer of an organic light emitting device.

Specifically, the compound may be used alone as a light emitting material, or may be used as a host material or a dopant material of the light emitting layer. When the compound represented by Formula 1 is used in the organic material layer, the driving voltage of the device can be lowered, the light efficiency can be improved, and the lifespan characteristics of the device can be improved by the thermal stability of the compound.

In addition, in the compound of Formula 1 according to the present invention, an N-containing ring is substituted at the 3rd carbon position of the dibenzofuran structure, and a phenylene group is a linking group to benzene in which the N-containing ring is not substituted in the structure of the dibenzofuran. As a result, since the phenylene group has a disubstituted substituent, the HOMO is delocalized to effectively stabilize the holes, thereby having a more electron-stable structure, thereby improving the device lifespan.

In particular, the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 may be simultaneously used as a material of the light emitting layer of the organic light emitting device. In this case, it is possible to lower the driving voltage of the device, improve the light efficiency, and particularly improve the lifespan characteristics of the device due to the thermal stability of the compound.

1 to 3 are views schematically showing a stacked structure of an organic light emitting device according to an exemplary embodiment of the present application, respectively.

Hereinafter, the present application will be described in detail.

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

In the present specification, the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, 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-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, and the like, but is not limited thereto.

In the present specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents. The carbon number of the alkenyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20. Specific examples include a 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 are not limited thereto.

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

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

In the present specification, the cycloalkyl group includes a monocyclic or polycyclic ring having 3 to 60 carbon atoms, and may be further substituted by other substituents. Here, polycyclic means a group in which a cycloalkyl group is directly connected to another ring group or condensed. Here, the other ring group may be a cycloalkyl group, but may be a different type of ring group, for example, a heterocycloalkyl group, an aryl group, a heteroaryl group, or the like. The carbon number of the cycloalkyl group may be 3 to 60, specifically 3 to 40, 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, and the like, but is not limited thereto.

In the present specification, the heterocycloalkyl group includes O, S, 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 other substituents. Here, polycyclic refers to a group in which a heterocycloalkyl group is directly connected or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may be a different type of ring group, for example, a cycloalkyl group, an aryl group, a heteroaryl group, or the like. The heterocycloalkyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 20 carbon atoms.

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 other substituents. Here, polycyclic means a group in which an aryl group is directly connected or condensed with another ring group. Here, the other ring group may be an aryl group, but may be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, and the like. The carbon number of the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25. Specific examples of the aryl group include a phenyl group, a biphenyl group, a triphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrethyl group a nyl group, a tetracenyl group, a pentacenyl group, an indenyl group, an acenaphthylenyl group, a 2,3-dihydro-1H-indenyl group, a condensed cyclic group thereof, and the like, but is not limited thereto.

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

,

,

,

,

,

등이 될 수 있으나, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

,

,

,

and the like, but is not limited thereto.

In the present specification, the heteroaryl group includes S, O, Se, N or Si as a hetero atom, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic refers to a group in which a heteroaryl group is directly connected or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may be a different type of ring group, for example, a cycloalkyl group, a heterocycloalkyl group, an aryl group, or the like. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 25 carbon atoms. Specific examples of the heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a 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, quinazolylyl group, naphthyridyl group, acridinyl group, phenanthridyl group Nyl group, imidazopyridinyl group, diazanaphthalenyl group, triazaindene 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, phenothiazinyl group, phthalazinyl group, naphthylidinyl group, phenanthrolinyl group, Benzo[c][1,2,5]thiadiazolyl group, 5,10-dihydrodibenzo[b,e][1,4]azasilinyl, 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 ] a carbazolyl group, and the like, but 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; an alkylarylamine group; an alkyl heteroarylamine group; And it may be selected from the group consisting of an aryl heteroarylamine group, the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluorene There is a nylamine group, a phenyltriphenylenylamine group, a biphenyltriphenylenylamine group, and the like, but is not limited thereto.

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

In the present specification, the phosphine oxide group is represented by -P(=O)R101R102, R101 and R102 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; an alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heterocyclic group. The phosphine oxide group specifically includes, but is not limited to, a diphenylphosphine oxide group, a dinaphthylphosphine oxide, and the like.

In the present specification, the silyl group is a substituent including Si and the Si atom is directly connected as a radical, and is represented by -SiR104R105R106, R104 to R106 are the same or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; an alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heterocyclic group. Specific examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. It is not limited.

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

The structures exemplified by the above-described cycloalkyl group, cycloheteroalkyl group, aryl group and heteroaryl group may be applied, except that the aliphatic or aromatic hydrocarbon ring or heterocycle that adjacent groups may form is not a monovalent group.

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

In the present specification, "substituted or unsubstituted" means C1 to C60 straight-chain or branched alkyl; C2 to C60 linear or branched alkenyl; C2 to C60 linear or branched 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 selected from the group consisting of It means that it is substituted or unsubstituted with one or more substituents, or substituted or unsubstituted with a substituent to which two or more substituents selected from the above-exemplified substituents are connected,

Wherein R, R' and R" are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 is a heteroaryl group of

In the present specification, "when 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 ( ² H, Deuterium) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

In the exemplary embodiment of the present application, "when a substituent is not indicated in the chemical formula or compound structure" may mean that all positions that may come as a substituent are hydrogen or deuterium. That is, in the case of deuterium, deuterium is an isotope of hydrogen, and some hydrogen atoms may be isotope deuterium, and the content of deuterium may be 0% to 100%.

In an exemplary embodiment of the present application, in "when a substituent is not indicated in the chemical formula or compound structure", the content of deuterium is 0%, the content of hydrogen is 100%, and all of the substituents explicitly exclude deuterium such as hydrogen If not, hydrogen and deuterium may be mixed and used in the compound.

In an exemplary embodiment of the present application, deuterium is one of the isotopes of hydrogen, and as an element having a deuteron consisting of one proton and one neutron as an atomic nucleus, hydrogen- It can be expressed as 2, and the element symbol can also be written as D or 2H.

In an exemplary embodiment of the present application, isotopes have the same atomic number (Z), but isotopes that have different mass numbers (A) have the same number of protons, but neutrons It can also be interpreted as an element with a different number of (neutron).

In the exemplary embodiment of the present application, the meaning of the content of specific substituents T% is T2 when the total number of substituents that the basic compound can have is defined as T1, and the number of specific substituents is defined as T2. It can be defined as /T1×100 = T%.

로 표시되는 페닐기에 있어 중수소의 함량 20%라는 것은 페닐기가 가질 수 있는 치환기의 총 개수는 5(식 중 T1)개이고, 그 중 중수소의 개수가 1(식 중 T2)인 경우 20%로 표시될 수 있다. 즉, 페닐기에 있어 중수소의 함량 20%라는 것인 하기 구조식으로 표시될 수 있다.That is, in one example,

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

In addition, in the exemplary embodiment of the present application, in the case of "a phenyl group having a deuterium content of 0%", it may mean a phenyl group that does not contain a deuterium atom, that is, has 5 hydrogen atoms.

In an exemplary embodiment of the present application, a heterocyclic compound represented by Formula 1 is provided.

In an exemplary embodiment of the present application, Chemical Formula 1 may be represented by Chemical Formula 3 below.

[Formula 3]

In Formula 3,

Definitions of R1, R2, L1, L2, Ar1, N-Het, a, b, p, m, and n are the same as those in Formula 1 above.

In an exemplary embodiment of the present application, Chemical Formula 1 may be represented by any one of Chemical Formulas 4 to 7 below.

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Formulas 4 to 7,

Definitions of R1, R2, L1 to L3, Ar1, Ar2, N-Het, a, b, c, d, p, m, and n are the same as in Formula 1 above.

In the case of having a specific substituent at the 1st position of dibenzofuran as shown in Chemical Formula 7, in particular, when Td is lower than when substituted at other places, thermal stability is excellent, and the lifespan characteristics of the organic light emitting device are particularly excellent. In the case of having a specific substituent at the 2-position of dibenzofuran as shown in Chemical Formula 6, triplet energy is high, and quantum efficiency is excellent due to good balance of charges. In the case of having a substituent at the 4th position of dibenzofuran as shown in Chemical Formula 4, in particular, the current density is better than that of the case where it is substituted elsewhere, so that the driving voltage is low and the triplet energy is high.

In the exemplary embodiment of the present application, in the case of Chemical Formulas 4, 6 and 7, when applied to a device than Chemical Formula 5 of the present application, the characteristics are more excellent, and a substituent is substituted at the 3rd position of dibenzofuran as shown in Chemical Formula 5 of the present application In this case, it was confirmed that the driving voltage was high and the efficiency was low compared to the cases of Chemical Formulas 4, 6 and 7 because T1 was low (2.48) because the conjugation was connected and the charge was not disconnected.

In an exemplary embodiment of the present application, Chemical Formula 3 may be represented by any one of Chemical Formulas 3-1 to 3-4 below.

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Formula 3-4]

In Formulas 3-1 to 3-4,

Definitions of R1, R2, L1, L2, Ar1, N-Het, a, b, p, m, and n are the same as those in Formula 3 above.

In an exemplary embodiment of the present application, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R201R202; and -NR201R202, or two or more groups adjacent to each other may combine with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle.

In another exemplary embodiment, R1 and R2 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, R1 and R2 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl group.

In another exemplary embodiment, R1 and R2 are the same as or different from each other, and each independently hydrogen; C1 to C40 alkyl group; C6 to C40 aryl group; Or it may be a C2 to C40 heteroaryl group.

In another exemplary embodiment, R1 and R2 are the same as or different from each other, and each independently hydrogen; C1 to C20 alkyl group; C6 to C20 aryl group; Or it may be a C2 to C20 heteroaryl group.

In another exemplary embodiment, R1 and R2 may be hydrogen.

In an exemplary embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C40 aryl group; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl group.

In another exemplary embodiment, Ar1 and Ar2 may be the same as or different from each other, and each independently may be a substituted or unsubstituted C6 to C40 aryl group.

In another exemplary embodiment, Ar1 and Ar2 may be the same as or different from each other, and may each independently represent a substituted or unsubstituted monocyclic or polycyclic C6 to C40 aryl group.

In another exemplary embodiment, Ar1 and Ar2 may be the same as or different from each other, and each independently a monocyclic or polycyclic C6 to C40 aryl group.

In another exemplary embodiment, Ar1 and Ar2 are the same as or different from each other, and each independently a monocyclic C6 to C10 aryl group; Or it may be a polycyclic C10 to C40 aryl group.

In another exemplary embodiment, Ar1 and Ar2 may be the same as or different from each other, and may each independently represent a monocyclic C6 to C10 aryl group.

In another exemplary embodiment, Ar1 and Ar2 may be the same as or different from each other, and may each independently be a phenyl group.

In an exemplary embodiment of the present application, L1 to L3 are the same as or different from each other and each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or it may be a substituted or unsubstituted C2 to C60 heteroarylene group.

In another exemplary embodiment, L1 to L3 are the same as or different from each other and each independently a direct bond; a substituted or unsubstituted C6 to C40 arylene group; Or it may be a substituted or unsubstituted C2 to C40 heteroarylene group.

In another exemplary embodiment, L1 to L3 are the same as or different from each other and each independently a direct bond; a substituted or unsubstituted C6 to C20 arylene group; Or it may be a substituted or unsubstituted C2 to C20 heteroarylene group.

In another exemplary embodiment, L1 to L3 are the same as or different from each other and each independently a direct bond; Or it may be a substituted or unsubstituted C6 to C20 arylene group.

In another exemplary embodiment, L1 to L3 are the same as or different from each other and each independently a direct bond; Or it may be a C6 to C20 arylene group.

In another exemplary embodiment, L1 to L3 are the same as or different from each other and each independently a direct bond; or a phenylene group.

In an exemplary embodiment of the present application, N-Het may be a substituted or unsubstituted, monocyclic or polycyclic C2 to C60 heterocyclic group containing one or more N.

In an exemplary embodiment of the present application, N-Het may be a monocyclic or polycyclic C2 to C60 heterocyclic group that is substituted or unsubstituted, and includes at least one bond of =N-.

In an exemplary embodiment of the present application, N-Het may be a monocyclic or polycyclic C2 to C60 heterocyclic group that is substituted or unsubstituted and includes one or more =N- bonds and no more than three bonds.

In another exemplary embodiment, N-Het may be a monocyclic or polycyclic C2 to C60 heterocyclic group that is substituted or unsubstituted, and contains 1 or more and 3 or less N.

In another exemplary embodiment, N-Het may be a monocyclic C2 to C60 heterocyclic group that is substituted or unsubstituted, and includes 1 or more and 3 or less N.

In another exemplary embodiment, N-Het may be a monocyclic C2 to C40 heterocyclic group that is substituted or unsubstituted, and includes 1 or more and 3 or less N.

In another exemplary embodiment, N-Het is unsubstituted or substituted with one or more substituents selected from the group consisting of a C6 to C40 aryl group and a C2 to C40 heteroaryl group, and N is one or more and three or less. It may be a monocyclic C2 to C40 heterocyclic group including.

In an exemplary embodiment of the present application, N-Het may be represented by the following Chemical Formula 1-1.

[Formula 1-1]

In Formula 1-1,

는 상기 화학식 1에 연결되는 위치를 의미하고,

means a position connected to Formula 1,

X1 to X3 are N; or CRm, and at least one of X1 to X3 is N,

L11 and L12 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group,

Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

wherein Rm is hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

a1 and c1 are integers from 0 to 4,

b1 and d1 are integers from 1 to 6.

In an exemplary embodiment of the present application, X1 may be N, and X2 and X3 may be CRm.

In an exemplary embodiment of the present application, X2 may be N, and X1 and X3 may be CRm.

In an exemplary embodiment of the present application, X1 may be CRm, and X2 and X3 may be N.

In an exemplary embodiment of the present application, X2 may be CRm, and X1 and X3 may be N.

In the exemplary embodiment of the present application, X1 to X3 may be N.

In an exemplary embodiment of the present application, L11 and L12 are the same as or different from each other and each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or it may be a substituted or unsubstituted C2 to C60 heteroarylene group.

In another exemplary embodiment, L11 and L12 are the same as or different from each other and each independently a direct bond; Or it may be a substituted or unsubstituted C6 to C60 arylene group.

In another exemplary embodiment, L11 and L12 are the same as or different from each other and each independently a direct bond; Or it may be a substituted or unsubstituted C6 to C40 arylene group.

In another exemplary embodiment, L11 and L12 are the same as or different from each other and each independently a direct bond; Or it may be a C6 to C40 arylene group.

In another exemplary embodiment, L11 and L12 are the same as or different from each other and each independently a direct bond; phenylene group; or a biphenylene group.

In an exemplary embodiment of the present application, Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C40 aryl group; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl group.

In another exemplary embodiment, Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic C6 to C40 aryl group; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl group.

In another exemplary embodiment, Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic C6 to C9 aryl group; a substituted or unsubstituted polycyclic C10 to C40 aryl group; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl group.

In another exemplary embodiment, Ar11 and Ar12 are the same as or different from each other, and each independently a monocyclic C6 to C9 aryl group; polycyclic C10 to C40 aryl group; Or it may be a C2 to C40 heteroaryl group unsubstituted or substituted with a C6 to C10 aryl group.

In another exemplary embodiment, Ar11 and Ar12 are the same as or different from each other, and each independently a phenyl group; biphenyl group; terphenyl group; dibenzofuran group; dibenzothiophene group; Or it may be a carbazole group unsubstituted or substituted with a phenyl group.

In an exemplary embodiment of the present application, at least one of Ar11 and Ar12 is a substituted or unsubstituted polycyclic C10 to C40 aryl group; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl group.

In another exemplary embodiment, at least one of Ar11 and Ar12 is a biphenyl group; terphenyl group; dibenzofuran group; dibenzothiophene group; Or it may be a carbazole group unsubstituted or substituted with a phenyl group.

In an exemplary embodiment of the present application, Rm is hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, Rm may be hydrogen.

In the exemplary embodiment of the present application, Chemical Formula 1-1 may be represented by any one of the following Chemical Formulas 1-1-1 to 1-1-3.

[Formula 1-1-1]

[Formula 1-1-2]

[Formula 1-1-3]

In the formulas 1-1-1 to 1-1-3,

X1 to X3, L11, Ar11, a1, b1, c1 and d1 have the same definitions as in Formula 1-1,

L22 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group,

Ar22 is a substituted or unsubstituted C6 to C10 monocyclic aryl group,

Ar23 is a substituted or unsubstituted C10 to C60 polycyclic aryl group,

Y is O; S; or NRn;

R21 to R24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R201R202; And -NR201R202, or two or more groups adjacent to each other combine with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle,

Rn is a substituted or unsubstituted C6 to C60 aryl group.

In particular, in Formula 1-1-2, when Ar23 has a polycyclic aryl group, and in Formula 1-1-3 when having a heteroaryl group with three or more rings, LUMO is widely spread and electron mobility is excellent, so it is a substituent In the case of having it, it has particularly excellent characteristics in terms of lifespan and efficiency.

In an exemplary embodiment of the present application, L22 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or it may be a substituted or unsubstituted C2 to C60 heteroarylene group.

In another embodiment, L22 is a direct bond; Or it may be a substituted or unsubstituted C6 to C60 arylene group.

In another embodiment, L22 is a direct bond; phenylene group; Or it may be a biphenylene group.

In an exemplary embodiment of the present application, Ar22 may be a substituted or unsubstituted C6 to C10 monocyclic aryl group.

In another exemplary embodiment, Ar22 may be a substituted or unsubstituted C6 to C8 monocyclic aryl group.

In another exemplary embodiment, Ar22 may be a C6 to C8 monocyclic aryl group.

In another exemplary embodiment, Ar22 may be a phenyl group.

In an exemplary embodiment of the present application, Ar23 may be a substituted or unsubstituted C10 to C60 polycyclic aryl group.

In another exemplary embodiment, Ar23 may be a substituted or unsubstituted C10 to C40 polycyclic aryl group.

In another exemplary embodiment, Ar23 may be a substituted or unsubstituted C10 to C30 polycyclic aryl group.

In another exemplary embodiment, Ar23 may be a C10 to C30 polycyclic aryl group.

In another exemplary embodiment, Ar23 is a biphenyl group; terphenyl group; naphthyl group; anthracenyl group; Or it may be a triphenylenyl group.

In an exemplary embodiment of the present application, R21 to R24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R201R202; and -NR201R202, or two or more groups adjacent to each other may combine with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 hetero ring.

In another exemplary embodiment, R21 to R24 may be hydrogen.

In an exemplary embodiment of the present application, Rn may be a substituted or unsubstituted C6 to C60 aryl group.

In another exemplary embodiment, Rn may be a substituted or unsubstituted C6 to C40 aryl group.

In another exemplary embodiment, Rn may be a C6 to C40 aryl group.

In another exemplary embodiment, Rn may be a monocyclic C6 to C40 aryl group.

In another exemplary embodiment, Rn may be a phenyl group.

In an exemplary embodiment of the present application, Chemical Formula 1 provides a heterocyclic compound represented by any one of the following compounds.

In addition, by introducing various substituents into the structure of Formula 1, compounds having intrinsic properties of the introduced substituents can be synthesized. For example, by introducing a substituent mainly used for a hole injection layer material, a hole transport material, a light emitting layer material, an electron transport layer material, and a charge generation layer material used in manufacturing an organic light emitting device into the core structure, the conditions required for each organic material layer are satisfied substances can be synthesized.

In addition, by introducing various substituents into the structure of Formula 1, it is possible to finely control the energy band gap, while improving the properties at the interface between organic materials and diversifying the use of the material.

On the other hand, the compound has a high glass transition temperature (Tg) and excellent thermal stability. This increase in thermal stability is an important factor in providing driving stability to the device.

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

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

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

In the exemplary embodiment of the present application, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound according to Formula 1 may be used as a material of the blue organic light emitting device.

In the exemplary embodiment of the present application, the organic light emitting device may be a green organic light emitting device, and the heterocyclic compound represented by Formula 1 may be used as a material of the green organic light emitting device.

In the exemplary embodiment of the present application, the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound represented by Formula 1 may be used as a material of the red organic light emitting device.

In the exemplary embodiment of the present application, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a light emitting layer material of the blue organic light emitting device.

In the exemplary embodiment of the present application, the organic light emitting device may be a green organic light emitting device, and the heterocyclic compound represented by Formula 1 may be used as a material for the light emitting layer of the green organic light emitting device.

In the exemplary embodiment of the present application, the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound represented by Formula 1 may be used as a material for the light emitting layer of the red organic light emitting device.

Specific details of the heterocyclic compound represented by Formula 1 are the same as described above.

The organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming one or more organic material layers using the above-described heterocyclic compound.

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

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

In the organic light emitting device of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include the heterocyclic compound of Formula 1 above.

In the organic light emitting device of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include the heterocyclic compound of Formula 1 as a light emitting layer host.

In the organic light emitting device according to an exemplary embodiment of the present application, the organic material layer including the heterocyclic compound represented by Formula 1 provides an organic light emitting device that further includes a heterocyclic compound represented by the following Formula 2 .

[Formula 2]

In Formula 2,

Rc and Rd are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiR10R11R12; -P(=O)R10R11; And -NR10R11, or two or more groups adjacent to each other combine with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle,

R10, R11, and R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

Ra and Rb are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

r and s are integers from 0 to 7.

When the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula 2 are included in the organic material layer of the organic light emitting device, better efficiency and lifespan effects are exhibited. This result can be expected to occur when both compounds are included at the same time exciplex (exciplex) phenomenon.

The exciplex phenomenon is a phenomenon in which energy having a size of a HOMO level of a donor (p-host) and a LUMO level of an acceptor (n-host) is emitted through electron exchange between two molecules. When an exciplex phenomenon occurs between two molecules, Reverse Intersystem Crossing (RISC) occurs, thereby increasing the internal quantum efficiency of fluorescence 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 the host of the emission layer, the driving voltage is because holes are injected into the p-host and electrons are injected into the n-host. can be lowered, thereby helping to improve lifespan.

In the exemplary embodiment of the present application, Chemical Formula 2 may be represented by the following Chemical Formula 2-1.

[Formula 2-1]

In Formula 2-1,

The definitions of Rc, Rd, r and s are the same as those in Formula 2 above,

Ra1 and Rb1 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group.

In the exemplary embodiment of the present application, Rc and Rd in Formula 2 and Formula 2-1 may be hydrogen.

In the exemplary embodiment of the present application, Ra1 and Rb1 in Formula 2-1 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C60 aryl group.

In another exemplary embodiment, Ra1 and Rb1 of Formula 2-1 may be the same as or different from each other, and may each independently represent a substituted or unsubstituted C6 to C40 aryl group.

In another exemplary embodiment, Ra1 and Rb1 in Formula 2-1 are the same as or different from each other, and each independently selected from the group consisting of a C1 to C40 alkyl group, a C6 to C40 aryl group, -CN and -SiR101R102R103 It may be a C6 to C40 aryl group unsubstituted or substituted with one or more substituents.

In another exemplary embodiment, Ra1 and Rb1 in Formula 2-1 are the same as or different from each other, and each independently a phenyl group, a phenyl group unsubstituted or substituted with -CN or -SiR101R102R103; a biphenyl group unsubstituted or substituted with a phenyl group; naphthyl group; a fluorene group unsubstituted or substituted with a methyl group or a phenyl group; spirobifluorene group; Or it may be a triphenylene group.

In the exemplary embodiment of the present application, R101, R102, and R103 of Formula 2-1 may be a phenyl group.

In an exemplary embodiment of the present application, definitions of R201, R202, R10, R11, and R12 may be the same as those of R101.

In an exemplary embodiment of the present application, the heterocyclic compound of Formula 2 may be represented by any one of the following compounds.

In addition, another exemplary embodiment of the present application provides a composition for an organic material layer of an organic light emitting device comprising the heterocyclic compound represented by Formula 1, and the heterocyclic compound represented by Formula 2 above.

Specific details of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 are the same as described above.

The weight ratio of the heterocyclic compound represented by Formula 1 in the composition to the heterocyclic compound represented by Formula 2 may be 1: 10 to 10: 1, 1: 8 to 8: 1, and 1: 5 to 5: 1 may be, and may be 1: 2 to 2: 1, but is not limited thereto.

The composition may be used when forming an organic material of an organic light emitting device, and in particular, it may be more preferably used when forming a host of a light emitting layer.

In an exemplary embodiment of the present application, the organic material layer includes the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2, and may be used together with a phosphorescent dopant.

In an exemplary embodiment of the present application, the organic material layer includes the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2, and may be used together with an iridium-based dopant.

As the phosphorescent dopant material, those known in the art may be used.

For example, phosphorescent dopant materials represented by LL'MX', LL'L"M, LMX'X", L2MX' and L3M may be used, but the scope of the present invention is not limited by these examples.

Here, L, L', L", X' and X" are different bidentate ligands, and M is a metal forming an octahedral complex.

M may be iridium, platinum, osmium, or the like.

L is an anionic bidentate ligand coordinated to M with the iridium-based dopant by sp2 carbon and a hetero atom, and X may function to trap electrons or holes. Non-limiting examples of L include 2-(1-naphthyl)benzoxazole, (2-phenylbenzoxazole), (2-phenylbenzothiazole), (2-phenylbenzothiazole), (7,8 -benzoquinoline), (thiophenepyrizine), phenylpyridine, benzothiophenepyrizine, 3-methoxy-2-phenylpyridine, thiophenepyrizine, tolylpyridine, and the like. Non-limiting examples of X' and X" include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate, and the like.

More specific examples are shown below, but are not limited to these examples.

In the exemplary embodiment of the present application, Ir(ppy) ₃ may be used as the green phosphorescent dopant as the iridium-based dopant.

In the exemplary embodiment of the present application, the content of the dopant may have a content of 1% to 15%, preferably 3% to 10%, more preferably 5% to 10% based on the entire emission layer.

In the organic light emitting device of the present invention, the organic material layer may include an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include the heterocyclic compound.

In another organic light emitting device, the organic material layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the heterocyclic compound.

In another organic light emitting device, the organic material layer may include an electron transport layer, a light emitting layer, or a hole blocking layer, and the electron transport layer, the light emitting layer or the hole blocking layer may include the heterocyclic compound.

The organic light emitting device of the present invention includes a light emitting layer, a hole injection layer, and a hole transport layer. It may further include one or more layers selected from the group consisting of an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer.

1 to 3 illustrate the stacking order of the electrode and the organic material layer of the organic light emitting device according to an exemplary embodiment of the present application. However, it is not intended that the scope of the present application be limited by these drawings, and the structure of an organic light emitting device known in the art may also be applied to the present application.

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

3 illustrates a case in which the organic material layer is multi-layered. The organic light emitting diode 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 such a laminated structure, and if necessary, the remaining layers except for the light emitting layer may be omitted, and other necessary functional layers may be further added.

In an exemplary embodiment of the present application, preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layer, wherein the forming of the organic material layer comprises forming one or more organic material layers using the composition for an organic material layer according to an exemplary embodiment of the present application. A method of manufacturing an organic light emitting device is provided.

In an exemplary embodiment of the present application, the forming of the organic material layer is formed by pre-mixing the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula 2 using a thermal vacuum deposition method. Provided is a method for manufacturing a phosphorus organic light emitting diode.

The pre-mixed refers to mixing the materials in one park before depositing the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula 2 on the organic layer.

The premixed material may be referred to as a composition for an organic material layer according to an exemplary embodiment of the present application.

The organic material layer including Formula 1 may further include other materials as needed.

The organic material layer including Chemical Formula 1 and Chemical Formula 2 may further include other materials as needed.

In the organic light-emitting device according to an exemplary embodiment of the present application, materials other than the compound of Formula 1 or Formula 2 are exemplified below, but these are for illustration only and not for limiting the scope of the present application, Materials known in the art may be substituted.

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

Materials having a relatively low work function may be used as the anode material, and a metal, metal oxide, conductive polymer, or the like may be used. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

As the hole injection material, a known hole injection material may be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or Advanced Material, 6, p.677 (1994). starburst-type amine derivatives such as tris(4-carbazolyl-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 or poly( 3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), polyaniline/Camphor sulfonic acid or polyaniline/ Poly(4-styrenesulfonate) (Polyaniline/Poly(4-styrene-sulfonate)) and the like may be used.

As the hole transport material, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, etc. may be used, and a low molecular weight or high molecular material may be used.

Examples of the electron transport material include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone Derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, etc. may be used, and polymer materials as well as low molecular weight materials may be used.

As the electron injection material, for example, LiF is typically used in the art, but the present application is not limited thereto.

A red, green, or blue light emitting material may be used as the light emitting material, and if necessary, two or more light emitting materials may be mixed and used. In this case, two or more light emitting materials may be deposited and used as individual sources, or may be premixed and deposited as a single source for use. In addition, although a fluorescent material can be used as a light emitting material, it can also be used as a phosphorescent material. As the light emitting material, a material that emits light by combining holes and electrons respectively injected from the anode and the cathode may be used alone, but materials in which a host material and a dopant material together participate in light emission may be used.

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

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

The heterocyclic compound according to an exemplary embodiment of the present application may act on a principle similar to that applied to an organic light emitting device in an organic electronic device including an organic solar cell, an organic photoreceptor, and an organic transistor.

Hereinafter, the present specification will be described in more detail through examples, but these are only for illustrating the present application and not for limiting the scope of the present application.

< production example >

< production example 1> Preparation of compound 1-2

1) Preparation of compound 1-2-3

Compound 7-bromo-1-chlorodibenzo [b, d] furan (7-bromo-1-chlorodibenzo [b, d] furan) 50.0 g (177.0 mM), bis (pinacolato) diboron (bis ( pinacolato) diboron) 89.9 g (354.0 mM), PdCl ₂ (dppf) 13.0 g (17.7 mM), KOAc 52.1 g (531.0 mM) were dissolved in 500 mL of 1,4-dioxane (1,4-dioxane) for 24 hours refluxed. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:5) to obtain 48.3 g (83%) of the target compound 1-2-3.

2) Preparation of compound 1-2-2

Compound 1-2-3 48.0 g (146.0 mM), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (2- ([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine) 50.2 g (292.0 mM), Pd (PPh) ₄ 8.4 g (7.3 mM), K ₂ CO ₃ 40.4 g (292.0 mM) was dissolved in 1,4-dioxane/H ₂ O 1000/200 mL and refluxed for 24 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:3) and recrystallized from methanol to obtain 51.4 g (69%) of the target compound 1-2-2.

3) Preparation of compound 1-2-1

Compound 1-2-2 51.0 g (100.0 mM), bis (pinacolato) diboron (bis (pinacolato) diboron) 50.8 g (200.0 mM), Pd (dba) ₂ 5.8 g (10.0 mM), XPhos 9.5 g (20.0 mM), 29.4 g (300.0 mM) of KOAc was dissolved in 1000 mL of 1,4-dioxane and refluxed for 24 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:5) to obtain 47.0 g (78%) of the target compound 1-2-1.

4) Preparation of compound 1-2

Compound 1-2-1 15.0 g (24.0 mM), 5'-bromo-1,1':3',1''-terphenyl (5'-bromo-1,1':3',1'' -terphenyl) 7.4 g (24.0 mM), Pd(PPh) ₄ 1.4 g (1.2 mM), K ₂ CO ₃ 6.6 g (48.0 mM) was dissolved in 1,4-dioxane/H ₂ O 200/40 mL for 24 hours refluxed. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:3) and recrystallized from methanol to obtain 13.7 g (81%) of the target compound 1-2.

2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (2-([1,1'-biphenyl) in Preparation Example 1 ]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine) using Intermediate A of Table 1 below and 5'-bromo-1,1':3',1'' -Terphenyl (5'-bromo-1,1':3',1''-terphenyl) was prepared in the same manner as in Preparation Example 1, except that Intermediate B of Table 1 was used instead of the target compound A was synthesized.

< production example 2> Preparation of compound 2-1

1) Preparation of compound 2-1-3

Compound 7-bromo-2-chlorodibenzo [b, d] furan (7-bromo-2-chlorodibenzo [b, d] furan) 50.0 g (177.0 mM), bis (pinacolato) diboron (bis ( pinacolato) diboron) 89.9 g (354.0 mM), PdCl ₂ (dppf) 13.0 g (17.7 mM), KOAc 52.1 g (531.0 mM) were dissolved in 500 mL of 1,4-dioxane (1,4-dioxane) for 24 hours refluxed. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:5) to obtain 47.1 g (81%) of the target compound 2-1-3.

2) Preparation of compound 2-1-2

Compound 2-1-3 47.0 g (143.0 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6-diphenyl-1,3,5-triazine) ) 38.3 g (143.0 mM), Pd(PPh) ₄ 8.3 g (7.2 mM), K ₂ CO ₃ 39.5 g (286.0 mM) were dissolved in 1,4-dioxane/H ₂ O 1000/200 mL and refluxed for 24 hours. . After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:4) and recrystallized from methanol to obtain 49.6 g (80%) of the target compound 2-1-2.

3) Preparation of compound 2-1-1

Compound 1-2-2 49.0 g (112.0 mM), bis (pinacolato) diboron (bis (pinacolato) diboron) 56.9 g (224.0 mM), Pd (dba) ₂ 6.4 g (11.2 mM), XPhos 10.7 g (22.4 mM), 33.0 g (336.0 mM) of KOAc was dissolved in 1000 mL of 1,4-dioxane and refluxed for 24 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:3) to obtain 45.9 g (78%) of the target compound 2-1-1.

4) Preparation of compound 2-1

Compound 2-1-1 15.0 g (28.0 mM), 5'-bromo-1,1':3',1''-terphenyl (5'-bromo-1,1':3',1'' -terphenyl) 8.7 g (28.0 mM), Pd(PPh) ₄ 1.6 g (1.4 mM), K ₂ CO ₃ 7.7 g (56.0 mM) was dissolved in 1,4-dioxane/H ₂ O 200/40 mL for 24 hours refluxed. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:4) and recrystallized from methanol to obtain 14.4 g (82%) of the target compound 2-1.

Intermediate A of Table 2 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in Preparation Example 2 (2-chloro-4,6-diphenyl-1,3,5-triazine) and 5'-bromo-1,1':3',1''-terphenyl (5'-bromo-1,1':3',1''-terphenyl) as an intermediate B in Table 2 below A target compound A was synthesized in the same manner as in Preparation Example 2, except that .

< production example 3> Preparation of compound 3-1

1) Preparation of compound 3-1-3

Compound 3-bromo-6-chlorodibenzo [b, d] furan (3-bromo-6-chlorodibenzo [b, d] furan) 50.0 g (177.0 mM), bis (pinacolato) diboron (bis ( pinacolato) diboron) 89.9 g (354.0 mM), PdCl ₂ (dppf) 13.0 g (17.7 mM), KOAc 52.1 g (531.0 mM) were dissolved in 500 mL of 1,4-dioxane (1,4-dioxane) for 24 hours refluxed. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:4) to obtain 48.3 g (83%) of the target compound 3-1-3.

2) Preparation of compound 3-1-2

Compound 3-1-3 48.0 g (146.0 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6-diphenyl-1,3,5-triazine) ) 39.1 g (146.0 mM), Pd(PPh) ₄ 8.4 g (7.3 mM), and K ₂ CO ₃ 40.4 g (292.0 mM) were dissolved in 1,4-dioxane/H ₂ O 1000/200 mL and refluxed for 24 hours. . After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:5) and recrystallized from methanol to obtain 47.5 g (75%) of the target compound 3-1-2.

3) Preparation of compound 3-1-1

Compound 3-1-2 47.0 g (108.0 mM), bis (pinacolato) diboron (bis (pinacolato) diboron) 54.9 g (216.0 mM), Pd (dba) ₂ 6.2 g (10.8 mM), XPhos 10.3 g (21.6 mM), 31.8 g (324.0 mM) of KOAc was dissolved in 1000 mL of 1,4-dioxane and refluxed for 24 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:5) to obtain 45.4 g (80%) of the target compound 3-1-1.

4) Preparation of compound 3-1

Compound 3-1-1 15.0 g (28.0 mM), 5'-bromo-1,1':3',1''-terphenyl (5'-bromo-1,1':3',1'' -terphenyl) 8.7 g (28.0 mM), Pd(PPh) ₄ 1.6 g (1.4 mM), K ₂ CO ₃ 7.7 g (56.0 mM) was dissolved in 1,4-dioxane/H ₂ O 200/40 mL for 24 hours refluxed. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and recrystallized from methanol to obtain 14.1 g (80%) of the target compound 3-1.

Intermediate A of Table 3 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in Preparation Example 3 (2-chloro-4,6-diphenyl-1,3,5-triazine) and 5'-bromo-1,1':3',1''-terphenyl (5'-bromo-1,1':3',1''-terphenyl) instead of Intermediate B in Table 3 below A target compound A was synthesized in the same manner as in Preparation Example 3, except that .

< production example 4> Synthesis of compound 4-3

1) Preparation of compound 4-3

3-bromo-1,1'-biphenyl 3.7g (15.8mM), 9-phenyl-9H,9'H-3,3'-bicarbazole 6.5g (15.8mM), CuI 3.0g (15.8mM) ), 1.9 mL (15.8 mM) of trans-1,2-diaminocyclohexane, and 3.3 g (31.6 mM) of K ₃ PO ₄ were dissolved in 100 mL of 1,4-oxane and refluxed for 24 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed by a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:3) and recrystallized from methanol to obtain 7.5 g (85%) of the target compound 4-3.

In Preparation Example 4, the intermediate A of Table 4 was used instead of 3-bromo-1,1′-biphenyl and the 9-phenyl-9H,9′H-3,3′-bicarbazole was replaced with Table 4 The target compound A was synthesized in the same manner as in Preparation Example 4, except that Intermediate B was used.

Heterocyclic compounds of Chemical Formulas 1 and 2 other than the compounds described in Preparation Examples 1 to 4 and Tables 1 to 4 were also prepared in the same manner as described in Preparation Examples.

Tables 5 and 6 below are ¹ H NMR data and FD-MS data of the synthesized compound, and it can be confirmed that the desired compound was synthesized through the following data.

compound
number ¹ H NMR (CDCl ₃ , 200 Mz) 1-2 δ = 8.28(2H, d), 7.95(1H, d), 7.85(2H, d), 7.75(2H, d), 7.62-7.66(5H, m), 7.41-7.52(19H, m), 7.25( 2H, d) 1-3 δ = 8.28 (2H, d), 8.24 (1H, d), 7.95 (1H, d), 7.41-7.75 (29H, m) 1-13 δ = 8.28 (2H, d), 7.95 (1H, d), 7.75 (2H, d), 7.62-7.66 (8H, m), 7.41-7.52 (24H, m) 1-14 δ = 8.28 (2H, d), 7.75-7.95 (6H, m), 7.62-7.66 (6H, m), 7.32-7.52 (17H, m) 1-17 δ = 8.28(2H, d), 8.24(1H, d), 7.95(2H, d), 7.89(1H, d), 7.32-7.75(29H, m) 1-25 δ = 8.45(1H, d), 8.28(2H, d), 8.24(1H, d), 7.95-8.11(5H, m), 7.41-7.75(26H, m) 1-34 δ = 8.28(2H, d), 8.18(1H, d), 8.12(1H, d), 8.00(1H, d), 7.95(1H, d), 7.77(1H, s), 7.75(2H, d) , 7.41-7.66 (26H, m), 7.29 (1H, t) 1-38 δ = 7.95 (1H, d), 7.85 (4H, d), 7.75 (2H, d), 7.62-7.66 (5H, m), 7.41-7.52 (21H, m), 7.25 (4H, d) 1-40 δ = 8.24 (2H, d), 7.95 (1H, d), 7.41-7.75 (34H, m) 1-41 δ = 7.95 (1H, d), 7.85 (4H, d), 7.75 (2H, d), 7.62-7.66 (5H, m), 7.41-7.52 (21H, m), 7.25 (8H, d) 1-59 δ = 7.95(1H, d), 7.85(2H, d), 7.75(2H, d), 7.62-7.66(8H, m), 7.41-7.52(26H, m), 7.25(2H, d) 1-61 δ = 7.75-7.95 (8H, m), 7.62-7.66 (6H, m), 7.25-7.52 (21H, m) 1-87 δ = 8.45(1H, d), 7.95-8.00(3H, m), 7.75-7.86(6H, m), 7.62-7.66(5H, m), 7.41-7.52(18H, m), 7.25(2H, d) ) 1-104 δ = 8.12-8.24(3H, m), 8.00(1H, d), 7.95(1H, d), 7.41-7.77(34H, m), 7.29(1H, t) 1-111 δ = 7.95 (1H, d), 7.85 (4H, d), 7.75 (2H, d), 7.62-7.66 (5H, m), 7.41-7.52 (21H, m), 7.25 (12H, d) 1-112 δ = 7.95 (1H, d), 7.85 (2H, d), 7.75 (2H, d), 7.62-7.66 (8H, m), 7.41-7.52 (26H, m), 7.25 (6H, d) 1-130 δ = 7.95 (1H, d), 7.75 (2H, d), 7.62-7.66 (11H, m), 7.41-7.52 (31H, m) 1-151 δ = 7.95 (1H, d), 7.89 (1H, d), 7.75 (3H, d), 7.62-7.66 (10H, m), 7.32-7.52 (24H, m) 1-158 δ = 8.45(1H, d), 8.41(1H, d), 8.20(1H, d), 7.98(1H, d), 7.95(1H, d), 7.85(4H, d), 7.75(2H, d) , 7.41-7.66 (24H, m), 7.25 (8H, d) 1-184 δ = 8.49(1H, d), 8.12(1H, d), 8.10(1H, d), 7.95(1H, d), 7.85(2H, d), 7.75(2H, d), 7.41-7.66(29H, m), 7.25-7.29 (7H, m) 2-1 δ = 8.28 (4H, d), 7.95 (1H, d), 7.64-7.81 (8H, m), 7.41-7.52 (16H, m) 2-3 δ = 8.28(2H, d), 8.24(1H, d), 7.95(1H, d), 7.64-7.81(9H, m), 7.41-7.57(20H, m) 2-4 δ = 8.28 (2H, d), 7.95 (1H, d), 7.64-7.85 (10H, m), 7.41-7.52 (18H, m), 7.25 (6H, d) 2-5 δ = 8.28 (2H, d), 7.95 (1H, d), 7.64-7.85 (11H, m), 7.41-7.57 (21H, m), 7.25 (2H, d) 2-14 δ = 8.28 (2H, d), 7.66-7.95 (13H, m), 7.32-7.52 (16H, m) 2-24 δ = 8.45(1H, d), 8.28(2H, d), 8.11(1H, d), 8.08(1H, s), 7.98(1H, d), 7.95(1H, d), 7.64-7.82(9H, m), 7.41-7.52 (15H, m) 2-34 δ = 8.28(2H, d), 8.18(1H, d), 8.12(1H, d), 8.00(1H, d), 7.95(1H, d), 7.41-7.81(29H, m), 7.29(1H, t) 2-39 δ = 8.24(1H, d), 7.95(1H, d), 7.64-7.85(11H, m), 7.41-7.52(22H, m), 7.25(2H, d) 2-40 δ = 8.24 (2H, d), 7.95 (1H, d), 7.66-7.81 (10H, m), 7.41-7.57 (24H, m) 2-47 δ = 8.24 (1H, d), 7.95 (1H, d), 7.66-7.85 (11H, m), 7.41-7.57 (22H, m), 7.25 (6H, d) 2-59 δ = 7.95 (1H, d), 7.64-7.85 (13H, m), 7.41-7.52 (25H, m), 7.25 (2H, d) 2-75 δ = 7.64-7.95 (15H, m), 7.25-7.52 (20H, m), 2-78 δ = 8.24 (1H, d), 7.25-7.95 (38H, m) 2-85 δ = 8.45(1H, d), 8.24(1H, d), 8.05-8.11(3H, m), 7.98(1H, d), 7.95(1H, d), 7.66-7.85(11H, m), 7.41- 7.57 (19H, m), 7.25 (2H, d) 2-103 δ = 8.18(1H, d), 8.12(1H, d), 8.00 (1H, d), 7.95(1H, d), 7.41-7.85(33H, m), 7.29(1H, t), 7.25(2H, d) 2-112 δ = 7.95 (1H, d), 7.64-7.85 (13H, m), 7.41-7.57 (23H, m), 7.25 (8H, d) 2-121 δ = 7.95 (1H, d), 7.64-7.85 (13H, m), 7.41-7.57 (25H, m), 7.25 (6H, d) 2-139 δ = 7.95 (2H, d), 7.89 (1H, d), 7.64-7.81 (14H, m), 7.32-7.52 (22H, m), 2-167 δ = 8.45(1H, d), 8.00 (1H, d), 7.98(1H, d), 7.95(1H, d), 7.64-7.86(12H, m), 7.41-7.52(17H, m), 7.25( 6H, d) 2-198 δ = 8.12(1H, d), 8.10(1H, d), 7.95(1H, d), 7.90(1H, d), 7.39-7.81(39H, m), 7.29(1H, t) 3-1 δ = 8.28(4H, d), 7.95(1H, d), 7.85(1H, d), 7.81(1H, d), 7.75(1H, d), 7.66(3H, s), 7.64(1H, s) , 7.38-7.52 (17H, m) 3-2 δ = 8.28(2H, d), 7.95(1H, d), 7.75-7.85(5H, m), 7.66(3H, s), 7.64(1H, s), 7.41-7.52(19H, m), 7.25( 2H, d) 3-5 δ = 8.28 (2H, d), 7.95 (1H, d), 7.66-7.85 (10H, m), 7.38-7.57 (22H, m), 7.25 (2H, d) 3-7 δ = 8.28(2H, d), 8.24(1H, d), 7.95(1H, d), 7.64-7.85(8H, m), 7.38-7.57(21H, m), 7.25(4H, d) 3-14 δ = 8.28 (2H, d), 7.75-7.95 (7H, m), 7.66 (4H, s), 7.64 (1H, s), 7.32-7.52 (17H, m) 3-26 δ = 8.45(1H, d), 8.28(2H, d), 8.00 (1H, d), 7.98(1H, d), 7.95(1H, d), 7.75-7.86(5H, m), 7.66(3H, s), 7.64 (1H, s), 7.38-7.52 (16H, m) 3-38 δ = 7.95(1H, d), 7.85(5H, d), 7.81 (1H, d), 7.75 (1H, d), 7.66(3H, s), 7.64(1H, s), 7.38-7.52(21H, m), 7.25 (4H, d) 3-39 δ = 8.24(1H, d), 7.95(1H, d), 7.66-7.85(10H, m), 7.38-7.57(23H, m), 7.25(2H, d) 3-41 δ = 7.95(1H, d), 7.85(5H, d), 7.81 (1H, d), 7.75 (1H, d), 7.66(3H, s), 7.64(1H, s), 7.38-7.52(21H, m), 7.25 (8H, d) 3-48 δ = 8.24(1H, d), 7.95(1H, d), 7.64-7.85(9H, m), 7.38-7.57(25H, m), 7.25(4H, d) 3-60 δ = 8.24 (1H, d), 7.95 (1H, d), 7.64-7.85 (11H, m), 7.38-7.57 (28H, m) 3-65 δ = 7.75-7.95 (9H, m), 7.66 (4H, s), 7.64 (2H, s), 7.25-7.52 (20H, m) 3-66 δ = 8.24 (1H, d), 7.32-7.95 (34H, m) 3-88 δ = 8.45(1H, d), 8.24(1H, d), 8.00 (1H, d), 7.98(1H, d), 7.95(1H, d), 7.64-7.86(10H, m), 7.38-7.57( 20H, m) 3-108 δ = 8.24(1H, d), 8.12(1H, d), 8.10(1H, d), 7.38-7.95(36H, m), 7.29(1H, t) 3-114 δ = 8.24(1H, d), 7.95(1H, d), 7.64-7.85(10H, m), 7.38-7.57(23H, m), 7.25(10H, d) 3-130 δ = 7.95(1H, d), 7.85(1H, d), 7.81 (1H, d), 7.75 (1H, d), 7.66(9H, s), 7.64(1H, s), 7.38-7.52(31H, m) 3-144 δ = 8.24 (1H, d), 7.66-7.95 (14H, m), 7.25-7.57 (24H, m) 3-176 δ = 8.45(1H, d), 8.24(1H, d), 7.98(1H, d), 7.95(1H, d), 7.94(1H, d), 7.66-7.85(11H, m), 7.38-7.57( 21H, m), 7.25 (6H, d) 3-179 δ = 8.51(1H, d), 8.18 (1H, d), 8.12(1H, d), 7.95(1H, d), 7.75-7.85(5H, m), 7.25-7.66(35H, m) 4-3 δ = 8.55(1H, d), 8.30(1H, d), 8.21-8.13(3H, m), 7.99-7.89(3H, m), 7.77-7.35(17H, m), 7.20-7.16(2H, m) ) 4-4 δ = 8.55(1H, d), 8.30(1H, d), 8.19-8.13(2H, m), 7.99-7.89(8H, m), 7.77-7.75(3H, m), 7.62-7.35(11H, m) ), 7.20-7.16 (2H, m) 4-7 δ = 8.55(1H, d), 8.31-8.30(3H, d), 8.19-8.13(2H, m), 7.99-7.89(5H, m), 7.77-7.75(5H, m), 7.62-7.35(14H) , m), 7.20-7.16 (2H, m) 4-31 δ = 8.55(1H, d), 8.30(1H, d), 8.21-8.13(4H, m), 7.99-7.89(4H, m), 7.77-7.35(20H, m), 7.20-7.16(2H, m) ) 4-32 δ = 8.55(1H, d), 8.30(1H, d), 8.21-8.13(3H, m), 7.99-7.89(8H, m), 7.77-7.35(17H, m), 7.20-7.16(2H, m) ) 4-42 δ = 8.55(1H, d), 8.30(1H, d), 8.19(1H, d), 8.13(1H, d), 7.99-7.89(12H, m), 7.77-7.75(5H, m), 7.58( 1H, d), 7.49-7.35 (8H, m), 7.20-7.16 (2H, m)

compound FD-MS compound FD-MS 1-2 m/z=703.26 (C ₅₁ H ₃₃ N ₃ O=703.83) 1-3 m/z=703.26 (C ₅₁ H ₃₃ N ₃ O=703.83) 1-13 m/z=779.29 (C ₅₇ H ₃₇ N ₃ O=779.92) 1-14 m/z=717.24 (C ₅₁ H ₃₁ N ₃ O ₂ =717.81) 1-17 m/z=793.27 (C ₅₇ H ₃₅ N ₃ O ₂ =793.91) 1-25 m/z=809.25 (C ₅₇ H ₃₅ N ₃ OS=809.97) 1-34 m/z=792.29 (C ₅₇ H ₃₆ N ₄ O=792.92) 1-38 m/z=779.29 (C ₅₇ H ₃₇ N ₃ O=779.92) 1-40 m/z=779.29 (C ₅₇ H ₃₇ N ₃ O=779.92) 1-41 m/z=855.32 (C ₆₃ H ₄₁ N ₃ O=856.02) 1-59 m/z=855.32 (C ₆₃ H ₄₁ N ₃ O=856.02) 1-61 m/z=793.27 (C ₅₇ H ₃₅ N ₃ O ₂ =793.91) 1-87 m/z=809.25 (C ₅₇ H ₃₅ N ₃ OS=809.97) 1-104 m/z=868.32 (C ₆₃ H ₄₀ N ₄ O=869.02) 1-111 m/z=931.36 (C ₆₉ H ₄₅ N ₃ O=932.12) 1-112 m/z=931.36 (C ₆₉ H ₄₅ N ₃ O=932.12) 1-130 m/z=931.36 (C ₆₉ H ₄₅ N ₃ O=932.12) 1-151 m/z=869.30 (C ₆₃ H ₃₉ N ₃ O ₂ =870.00) 1-158 m/z=961.31 (C ₆₉ H ₄₃ N ₃ OS=962.16) 1-184 m/z=944.35 (C ₆₉ H ₄₄ N ₄ O=945.11) 2-1 m/z=627.23 (C ₄₅ H ₂₉ N ₃ O=627.73) 2-3 m/z=703.26 (C ₅₁ H ₃₃ N ₃ O=703.83) 2-4 m/z=779.29 (C ₅₇ H ₃₇ N ₃ O=779.92) 2-5 m/z=779.29 (C ₅₇ H ₃₇ N ₃ O=779.92) 2-14 m/z=717.24 (C ₅₁ H ₃₁ N ₃ O ₂ =717.81) 2-24 m/z=733.52 (C ₅₁ H ₃₁ N ₃ OS=733.88) 2-34 m/z=792.29 (C ₅₇ H ₃₆ N ₄ O=792.92) 2-39 m/z=779.29 (C ₅₇ H ₃₇ N ₃ O=779.92) 2-40 m/z=779.29 (C ₅₇ H ₃₇ N ₃ O=779.92) 2-47 m/z=855.32 (C ₆₃ H ₄₁ N ₃ O=856.02) 2-59 m/z=855.32 (C ₆₃ H ₄₁ N ₃ O=856.02) 2-75 m/z=793.27 (C ₅₇ H ₃₅ N ₃ O ₂ =793.91) 2-78 m/z=869.30 (C ₆₃ H ₃₉ N ₃ O ₂ =870.00) 2-85 m/z=885.28 (C ₆₃ H ₃₉ N ₃ OS=886.07) 2-103 m/z=868.32 (C ₆₃ H ₄₀ N ₄ O=869.02) 2-112 m/z=931.36 (C ₆₉ H ₄₅ N ₃ O=932.12) 2-121 m/z=931.36 (C ₆₉ H ₄₅ N ₃ O=932.12) 2-139 m/z=869.30 (C ₆₃ H ₃₉ N ₃ O ₂ =870.00) 2-167 m/z=885.28 (C ₆₃ H ₃₉ N ₃ OS=886.07) 2-198 m/z=944.35 (C ₆₉ H ₄₄ N ₄ O=945.11) 3-1 m/z=627.23 (C ₄₅ H ₂₉ N ₃ O=627.73) 3-2 m/z=703.26 (C ₅₁ H ₃₃ N ₃ O=703.83) 3-5 m/z=779.29 (C ₅₇ H ₃₇ N ₃ O=779.92) 3-7 m/z=779.29 (C ₅₇ H ₃₇ N ₃ O=779.92) 3-14 m/z=717.24 (C ₅₁ H ₃₁ N ₃ O ₂ =717.81) 3-26 m/z=733.22 (C ₅₁ H ₃₁ N ₃ OS=733.88) 3-38 m/z=779.29 (C ₅₇ H ₃₇ N ₃ O=779.92) 3-39 m/z=779.29 (C ₅₇ H ₃₇ N ₃ O=779.92) 3-41 m/z=855.32 (C ₆₃ H ₄₁ N ₃ O=856.02) 3-48 m/z=855.32 (C ₆₃ H ₄₁ N ₃ O=856.02) 3-60 m/z=855.32 (C ₆₃ H ₄₁ N ₃ O=856.02) 3-65 m/z=793.27 (C ₅₇ H ₃₅ N ₃ O ₂ =793.91) 3-66 m/z=793.27 (C ₅₇ H ₃₅ N ₃ O ₂ =793.91) 3-88 m/z=809.25 (C ₅₇ H ₃₅ N ₃ OS=809.97) 3-108 m/z=868.32 (C ₆₃ H ₄₀ N ₄ O=869.02) 3-114 m/z=931.36 (C ₆₉ H ₄₅ N ₃ O=932.12) 3-130 m/z=931.36 (C ₆₉ H ₄₅ N ₃ O=932.12) 3-144 m/z=869.30 (C ₆₃ H ₃₉ N ₃ O ₂ =870.00) 3-176 m/z=961.31 (C ₆₉ H ₄₃ N ₃ OS=962.16) 3-179 m/z=944.35 (C ₆₉ H ₄₄ N ₄ O=945.11) 4-3 m/z= 560.23 (C ₄₂ H ₂₈ N ₂ =560.70) 4-4 m/z= 560.23 (C ₄₂ H ₂₈ N ₂ =560.70) 4-7 m/z= 636.26 (C ₄₈ H ₃₂ N ₂ =636.80) 4-31 m/z= 636.26 (C ₄₈ H ₃₂ N ₂ =636.80) 4-32 m/z= 636.26 (C ₄₈ H ₃₂ N ₂ =636.80) 4-42 m/z= 636.26 (C ₄₈ H ₃₂ N ₂ =636.78)

< Experimental example 1>- Fabrication of organic light emitting device

A glass substrate coated with a thin film of ITO to a thickness of 1,500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic washing was performed with a solvent such as acetone, methanol, isopropyl alcohol, etc., dried, and UVO-treated for 5 minutes using UV in a UV washer. After transferring the substrate to a plasma cleaner (PT), plasma treatment was performed to remove the ITO work function and residual film in a vacuum state, and then transferred to a thermal deposition equipment for organic deposition.

The hole injection layer 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine) as a common layer on the ITO transparent electrode (anode) and the hole transport layer NPB (N,N'-Di ( 1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) was formed.

A light emitting layer was deposited thereon by thermal vacuum deposition as follows. The emission layer was deposited by depositing 400 Å of the compound shown in Table 7 as a host, and a green phosphorescent dopant was deposited by doping Ir(ppy) ₃ with 7% of the emission thickness of the emission layer. After that, 60 Å of BCP was deposited as a hole blocking layer, and 200 Å of Alq3 was deposited thereon as an electron transporting layer. Finally, lithium fluoride (LiF) is deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode is deposited to a thickness of 1,200 Å on the electron injection layer to form a cathode. An electroluminescent device was manufactured.

On the other hand, all organic compounds required for manufacturing OLED devices were vacuum sublimated and purified under 10 ^-6 to 10 ^-8 torr for each material and used for OLED manufacturing.

The electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured with M7000 of McScience, and the reference luminance was 6,000 through the life instrumentation measuring device (M6000) manufactured by McScience with the measurement result. At cd/m ² , T ₉₀ was measured.

The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifespan of the organic light emitting device manufactured above are shown in Table 7 below.

light emitting layer
compound drive voltage
(V) efficiency
(cd/A) color coordinates
(x, y) life span
(T ₉₀ ) Example 1 1-2 4.31 55.9 (0.245, 0.687) 270 Example 2 1-3 4.29 58.8 (0.244, 0.675) 281 Example 3 1-13 4.29 54.5 (0.249, 0.683) 265 Example 4 1-14 4.35 54.1 (0.243, 0.673) 251 Example 5 1-17 4.35 53.5 (0.251, 0.684) 241 Example 6 1-25 4.33 56.1 (0.247, 0.675) 244 Example 7 1-34 4.45 56.4 (0.248, 0.682) 237 Example 8 1-38 4.48 54.1 (0.245, 0.686) 262 Example 9 1-40 4.27 52.6 (0.243, 0.679) 265 Example 10 1-41 4.17 50.8 (0.242, 0.668) 254 Example 11 1-59 4.28 55.8 (0.247, 0.685) 259 Example 12 1-61 4.21 56.9 (0.241, 0.668) 247 Example 13 1-87 4.22 56.3 (0.251, 0.672) 234 Example 14 1-104 4.20 57.0 (0.240, 0.674) 241 Example 15 1-111 4.28 55.3 (0.242, 0.683) 252 Example 16 1-112 4.19 54.5 (0.231, 0.667) 249 Example 17 1-130 4.21 55.6 (0.241, 0.671) 244 Example 18 1-151 4.27 55.7 (0.231, 0.682) 256 Example 19 1-158 4.30 50.1 (0.231, 0.677) 236 Example 20 1-184 4.01 56.3 (0.246, 0.673) 231 Example 21 2-1 4.44 54.9 (0.246, 0.688) 268 Example 22 2-3 4.41 55.7 (0.245, 0.677) 265 Example 23 2-4 4.35 55.3 (0.250, 0.681) 261 Example 24 2-5 4.28 53.2 (0.242, 0.684) 248 Example 25 2-14 4.31 52.6 (0.251, 0.673) 237 Example 26 2-24 4.42 56.0 (0.247, 0.672) 239 Example 27 2-34 4.33 55.4 (0.251, 0.682) 240 Example 28 2-39 4.47 56.1 (0.245, 0.682) 255 Example 29 2-40 4.36 53.7 (0.241, 0.681) 253 Example 30 2-47 4.28 51.5 (0.241, 0.672) 241 Example 31 2-59 4.30 54.7 (0.247, 0.686) 245 Example 32 2-75 4.22 54.9 (0.247, 0.668) 251 Example 33 2-78 4.29 55.3 (0.251, 0.672) 246 Example 34 2-85 4.31 57.0 (0.241, 0.673) 238 Example 35 2-103 4.32 56.3 (0.242, 0.673) 249 Example 36 2-112 4.27 53.5 (0.241, 0.671) 245 Example 37 2-121 4.19 52.6 (0.231, 0.667) 244 Example 38 2-139 4.35 55.9 (0.241, 0.672) 231 Example 39 2-167 4.32 51.1 (0.230, 0.667) 228 Example 40 2-198 4.17 57.3 (0.247, 0.673) 234 Example 41 3-1 4.40 54.4 (0.243, 0.676) 267 Example 42 3-2 4.36 55.1 (0.244, 0.676) 265 Example 43 3-5 4.32 54.2 (0.247, 0.682) 260 Example 44 3-7 4.31 54.3 (0.242, 0.671) 261 Example 45 3-14 4.32 54.4 (0.251, 0.674) 251 Example 46 3-26 4.37 55.2 (0.252, 0.669) 242 Example 47 3-38 4.44 55.3 (0.238, 0.672) 252 Example 48 3-39 4.41 52.0 (0.245, 0.676) 255 Example 49 3-41 4.43 53.7 (0.253, 0.689) 249 Example 50 3-48 4.25 51.7 (0.232, 0.678) 244 Example 51 3-60 4.26 54.5 (0.247, 0.665) 247 Example 52 3-65 4.19 55.4 (0.241, 0.678) 253 Example 53 3-66 4.23 55.2 (0.251, 0.672) 258 Example 54 3-88 4.27 56.1 (0.240, 0.684) 235 Example 55 3-108 4.31 54.0 (0.232, 0.673) 240 Example 56 3-114 4.22 53.4 (0.241, 0.667) 248 Example 57 3-130 4.28 55.6 (0.252, 0.671) 244 Example 58 3-144 4.30 56.7 (0.231, 0.662) 242 Example 59 3-176 4.31 52.2 (0.230, 0.687) 253 Example 60 3-179 4.11 51.0 (0.236, 0.673) 249 Comparative Example 1 4-3 2.63 29.2 (0.233, 0.671) 45 Comparative Example 2 4-4 2.59 31.3 (0.231, 0.673) 48 Comparative Example 3 4-7 2.61 30.4 (0.237, 0.677) 44 Comparative Example 4 4-31 2.65 30.8 (0.234, 0.674) 43 Comparative Example 5 4-32 2.58 29.8 (0.231, 0.681) 44 Comparative Example 6 4-42 2.59 30.1 (0.233, 0.682) 43 Comparative Example 7 Ref. One 5.82 37.8 (0.235, 0.686) 54 Comparative Example 8 Ref. 2 5.91 36.5 (0.235, 0.667) 55 Comparative Example 9 Ref. 3 6.68 34.4 (0.237, 0.676) 51 Comparative Example 10 Ref. 4 6.23 33.7 (0.233, 0.675) 52 Comparative Example 11 Ref. 5 6.98 30.1 (0.231, 0.682) 65 Comparative Example 12 Ref. 6 6.14 32.7 (0.235, 0.672) 75 Comparative Example 13 Ref. 7 5.97 33.0 (0.233, 0.665) 69 Comparative Example 14 Ref. 8 5.84 36.2 (0.237, 0.677) 64

As can be seen from the results in Table 7, the organic electroluminescent device using the light emitting layer material of the organic electroluminescent device of the present invention has a lower driving voltage and improved luminous efficiency as well as significantly improved lifespan compared to Comparative Examples 7 to 13. .

As in the compounds of Comparative Examples 7 and 8, when there is no substituent on one benzene ring of the dibenzofuran of Formula 1, the electron mobility is lowered, and the balance of holes and electrons in the light emitting layer is broken, thereby reducing the lifespan.

As in the compounds of Comparative Examples 9 and 10, when the composition of the substituents of Chemical Formula 1 is the same but the positions are different, it was confirmed that the lifespan was reduced due to structural instability due to steric hindrance between the substituents.

In the case of having a linear structure like the compound of Comparative Example 11, it was confirmed that the conjugation was connected and the charge was not disconnected, and thus T1 was lowered to 2.48, thereby increasing the driving voltage and lowering the efficiency.

In addition, as in the compounds of Comparative Examples 12, 13 and 14, a heteroaryl group or a phenylene group on the other benzene ring side other than the benzene ring substituted with the N-Het substituent in the benzene ring of the dibenzofuran of Formula 1 herein It was confirmed that, when it has a linking group and does not have a substituent in which the phenylene group is disubstituted, the HOMO is localized, and the hole cannot be effectively stabilized and the lifespan is reduced.

< Experimental example 2>- Fabrication of organic light emitting device

A glass substrate coated with a thin film of ITO to a thickness of 1,500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic washing was performed with a solvent such as acetone, methanol, isopropyl alcohol, etc., dried, and UVO-treated for 5 minutes using UV in a UV washer. After transferring the substrate to a plasma cleaner (PT), plasma treatment was performed to remove the ITO work function and residual film in a vacuum state, and then transferred to a thermal deposition equipment for organic deposition.

The hole injection layer 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine) as a common layer on the ITO transparent electrode (anode) and the hole transport layer NPB (N,N'-Di ( 1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) was formed.

A light emitting layer was deposited thereon by thermal vacuum deposition as follows. The light emitting layer was pre-mixed with one heterocyclic compound described in Formula 1 and one heterocyclic compound described in Formula 2 as a host, and after preliminary mixing, 400 Å was deposited in one park, and the green phosphorescent dopant Ir(ppy) ₃ was deposited as a light emitting layer Deposited by doping 7% of the thickness. After that, 60 Å of BCP was deposited as a hole blocking layer, and 200 Å of Alq3 was deposited thereon as an electron transporting layer. Finally, lithium fluoride (LiF) is deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode is deposited to a thickness of 1,200 Å on the electron injection layer to form a cathode. An electroluminescent device was manufactured.

On the other hand, all organic compounds required for manufacturing OLED devices were vacuum sublimated and purified under 10 ^-6 to 10 ^-8 torr for each material and used for OLED manufacturing.

The electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured with M7000 of McScience, and the reference luminance was 6,000 through the life instrumentation measuring device (M6000) manufactured by McScience with the measurement result. At cd/m ² , T ₉₀ was measured.

The results of measuring the driving voltage, luminous efficiency, color coordinate (CIE), and lifespan of the organic light emitting diode manufactured according to the present invention are shown in Table 8 below.

light emitting layer
compound ratio drive voltage
(V) efficiency
(cd/A) color coordinates
(x, y) life span
(T ₉₀ ) Comparative Example 15 Ref. 4 :
4-32 1: 2 3. 88 73.7 (0.241, 0.715) 442 Comparative Example 16 1:1 3.89 71.5 (0.242, 0.721) 479 Comparative Example 17 2:1 3.65 76.9 (0.241, 0.712) 495 Comparative Example 18 Ref. 6:
4-32 1: 2 3.97 71.7 (0.242, 0.721) 443 Comparative Example 19 1:1 3.85 72.5 (0.252, 0.711) 482 Comparative Example 20 2:1 3.51 76.9 (0.231, 0.713) 489 Example 41 1-2: 4-31 1: 2 4.13 79.4 (0.252, 0.726) 537 Example 42 1:1 3.75 80.6 (0.231, 0.711) 581 Example 43 2:1 3.82 75.2 (0.232, 0.716) 523 Example 44 1-2 : 4-42 1: 2 4.11 79.5 (0.242, 0.724) 546 Example 45 1:1 3.66 79.6 (0.232, 0.711) 535 Example 46 2:1 3.75 75.9 (0.233, 0.720) 524 Example 47 1-14: 4-7 1: 2 4.25 77.4 (0.252, 0.715) 512 Example 48 1:1 3.85 80.1 (0.232, 0.711) 558 Example 49 2:1 3.89 77.4 (0.234, 0.712) 521 Example 50 2-3 : 4-31 1: 2 4.12 78.4 (0.212, 0.714) 522 Example 51 1:1 3.78 80.4 (0.221, 0.721) 555 Example 52 2:1 3.83 76.8 (0.231, 0.711) 488 Example 53 2-3 : 4-42 1: 2 4.11 79.5 (0.241, 0.712) 530 Example 54 1:1 3.74 80.4 (0.251, 0.714) 575 Example 55 2:1 3.91 75.9 (0.233, 0.714) 503 Example 56 2-5: 4-32 1: 2 4.22 76.3 (0.231, 0.713) 520 Example 57 1:1 3.94 80.5 (0.231, 0.711) 571 Example 58 2:1 3.90 73.8 (0.251, 0.712) 515 Example 59 2-5: 4-31 1: 2 4.17 78.2 (0.243, 0.715) 518 Example 60 1:1 3.79 79.9 (0.241, 0.710) 569 Example 61 2:1 3.89 72.8 (0.242, 0.712) 499 Example 62 2-65: 4-42 1: 2 3.91 70.6 (0.251, 0.716) 445 Example 61 1:1 3.78 76.1 (0.231, 0.711) 501 Example 62 2:1 3.82 68.4 (0.232, 0.711) 483 Example 63 3-1 : 4-3 1:8 4.87 54.2 (0.243, 0.713) 314 Example 64 1: 5 4.65 57.6 (0.233, 0.714) 355 Example 65 1: 2 4.23 77.3 (0.251, 0.712) 497 Example 66 1:1 3.71 75.9 (0.241, 0.714) 481 Example 67 2:1 3.85 72.2 (0.211, 0.712) 470 Example 68 5 : 1 4.43 67.3 (0.241, 0.721) 406 Example 69 8:1 4.64 51.7 (0.247, 0.727) 363 Example 70 3-2 : 4-4 1: 3 4.41 67.2 (0.231, 0.715) 405 Example 71 1: 2 4. 24 75.9 (0.241, 0.712) 505 Example 72 1:1 3.97 75.2 (0.252, 0.712) 481 Example 73 2:1 3.96 73.8 (0.242, 0.714) 462 Example 74 3 : 1 4.19 69.9 (0.231, 0.711) 434 Example 75 3-41 : 4-7 1: 2 4.28 77.7 (0.242, 0.714) 491 Example 76 1:1 3.85 79.4 (0.231, 0.713) 529 Example 77 2:1 3.92 75.8 (0.251, 0.713) 471

Looking at the results of Tables 7 and 8, it was confirmed that when the compound of Formula 1 and the compound of Formula 2 were included at the same time, better efficiency and lifespan effect were exhibited. This result can be expected to occur when both compounds are included at the same time exciplex (exciplex) phenomenon

The exciplex phenomenon is a phenomenon in which energy having a size of a HOMO level of a donor (p-host) and a LUMO level of an acceptor (n-host) is emitted 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 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 the host of the emission layer, the driving voltage is because holes are injected into the p-host and electrons are injected into the n-host. can be lowered, thereby helping to improve lifespan. In the present invention, it was confirmed that the donor role was the compound of Formula 2, and the acceptor role exhibited excellent device characteristics when the compound of Formula 1 was used as a host for the emission layer.

100: substrate
200: positive electrode
300: organic layer
301: hole injection layer
302: hole transport layer
303: light emitting layer
304: hole blocking layer
305: electron transport layer
306: electron injection layer
400: cathode

Claims (17)

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

In Formula 1,
N-Het is a substituted or unsubstituted, monocyclic or polycyclic C2 to C60 heterocyclic group containing one or more N,
L1 to L3 are the same as or different from each other and each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group,
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R201R202; And -NR201R202, or two or more groups adjacent to each other combine with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle,
m, c and p are integers from 0 to 4;
n and d are integers from 1 to 6,
a and b are integers from 0 to 3,
wherein R201 and R202 are a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group. The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formula 3:
[Formula 3]

In Formula 3,
Definitions of R1, R2, L1, L2, Ar1, N-Het, a, b, p, m, and n are the same as those in Formula 1 above. The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 4 to 7:
[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Formulas 4 to 7,
Definitions of R1, R2, L1 to L3, Ar1, Ar2, N-Het, a, b, c, d, p, m, and n are the same as in Formula 1 above. The heterocyclic compound according to claim 1, wherein N-Het is represented by the following Chemical Formula 1-1:
[Formula 1-1]

In Formula 1-1,

means a position connected to Formula 1,
X1 to X3 are N; or CRm, and at least one of X1 to X3 is N,
L11 and L12 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group,
Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
wherein Rm is hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
a1 and c1 are integers from 0 to 4,
b1 and d1 are integers from 1 to 6. The heterocyclic compound according to claim 4, wherein Formula 1-1 is represented by any one of the following Formulas 1-1-1 to 1-1-3:
[Formula 1-1-1]

[Formula 1-1-2]

[Formula 1-1-3]

In the formulas 1-1-1 to 1-1-3,
X1 to X3, L11, Ar11, a1, b1, c1 and d1 have the same definitions as in Formula 1-1,
L22 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group,
Ar22 is a substituted or unsubstituted C6 to C10 monocyclic aryl group,
Ar23 is a substituted or unsubstituted C10 to C60 polycyclic aryl group,
Y is O; S; or NRn;
R21 to R24 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R201R202; And -NR201R202, or two or more groups adjacent to each other combine with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle,
R201 and R202 are the same as defined in Formula 1,
Rn is a substituted or unsubstituted C6 to C60 aryl group. The heterocyclic compound according to claim 1, wherein Formula 1 is represented by any one of the following compounds:

a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer comprises the heterocyclic compound according to any one of claims 1 to 6 phosphorus organic light emitting device. The organic light-emitting device according to claim 7, wherein the organic material layer including the heterocyclic compound further comprises a heterocyclic compound represented by the following Chemical Formula 2:
[Formula 2]

In Formula 2,
Rc and Rd are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiR10R11R12; -P(=O)R10R11; And -NR10R11, or two or more groups adjacent to each other combine with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle,
R10, R11, and R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
Ra and Rb are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
r and s are integers from 0 to 7. The organic light-emitting device according to claim 8, wherein the heterocyclic compound represented by Formula 2 is any one selected from the following compounds:

The organic light emitting diode of claim 8, wherein Rc and Rd are hydrogen. The organic light emitting diode of claim 7, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound of Formula 1 above. The organic light-emitting device of claim 7 , wherein the organic material layer includes an emission layer, the emission layer includes a host material, and the host material includes the heterocyclic compound of Formula 1 above. The method according to claim 7, wherein the organic light emitting device is a light emitting layer, a hole injection layer, a hole transport layer. An organic light-emitting device that further comprises one or more layers selected from the group consisting of an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. A composition for an organic material layer of an organic light emitting device comprising the heterocyclic compound according to any one of claims 1 to 6 and the heterocyclic compound represented by the following Chemical Formula 2:
[Formula 2]

In Formula 2,
Rc and Rd are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiR10R11R12; -P(=O)R10R11; And two or more groups selected from the group consisting of a substituted or unsubstituted amine group, or adjacent to each other are combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 hetero ring, ,
R10, R11, and R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
Ra and Rb are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
r and s are integers from 0 to 7. The composition for an organic material layer of an organic light emitting device according to claim 14, wherein the weight ratio of the heterocyclic compound in the composition to the heterocyclic compound represented by Chemical Formula 2 is 1:10 to 10:1. preparing a substrate;
forming a first electrode on the substrate;
forming one or more organic material layers on the first electrode; and
forming a second electrode on the organic material layer;
The method of manufacturing an organic light emitting device, wherein the forming of the organic material layer includes forming one or more organic material layers using the composition for an organic material layer according to claim 14 . The organic light-emitting device of claim 16 , wherein the forming of the organic material layer is formed by pre-mixing the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula 2 using a thermal vacuum deposition method. manufacturing method.

Images