KR102856109B1 - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel compound and an organic light-emitting device using the same.

Description

Novel compound and organic light emitting device comprising the same

The present invention relates to a novel compound and an organic light-emitting device comprising the same.

Organic light-emitting diodes (OLEDs) generally refer to the conversion of electrical energy into light energy using organic materials. Organic light-emitting devices utilizing this phenomenon boast a wide viewing angle, excellent contrast, and fast response times, and are actively researched due to their superior brightness, operating voltage, and response speed characteristics.

Organic light-emitting devices generally have a structure including an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer is often composed of a multilayer structure composed of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of such an organic light-emitting device, when a voltage is applied between two electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when these excitons fall back to the ground state, light is emitted.

There is a continuous demand for the development of new materials for organic materials used in organic light-emitting devices such as the above.

Korean Patent Publication No. 10-2000-0051826

The present invention relates to a novel compound and an organic light-emitting device comprising the same.

The present invention provides a compound represented by the following chemical formula 1:

[Chemical Formula 1]

In the above chemical formula 1,

HAr is a substituted or unsubstituted pyrimidinyl; or a substituted or unsubstituted triazinyl,

L ₁ and L ₂ are each independently unsubstituted or deuterium substituted C _6-60 arylene,

D stands for deuterium,

n is an integer from 0 to 3.

In addition, the present invention provides an organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers includes a compound represented by the chemical formula 1.

The compound represented by the above-described chemical formula 1 can be used as a material of an organic layer of an organic light-emitting device, and can improve efficiency, low driving voltage, and/or lifespan characteristics in the organic light-emitting device.

Figure 1 illustrates an example of an organic light-emitting device composed of a substrate (1), an anode (2), a hole transport layer (3), a light-emitting layer (4), an electron injection and transport layer (5), and a cathode (6).
Figure 2 illustrates an example of an organic light-emitting device composed of a substrate (1), an anode (2), a hole injection layer (7), a hole transport layer (3), an electron blocking layer (8), a light-emitting layer (4), a hole blocking layer (9), an electron injection and transport layer (5), and a cathode (6).

Hereinafter, the present invention will be described in more detail to help understand it.

(Definition of terms)

In this specification, and means a bond connecting to another substituent, and "D" means deuterium.

The term "substituted or unsubstituted" as used herein means a group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkylsulfoxy group; an arylsulfoxy group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; a heteroarylamine group; an arylphosphine group; or a heterocyclic group containing one or more of N, O, and S atoms, or a heterocyclic group unsubstituted or substituted with a substituent in which two or more of the above-mentioned substituents are linked. For example, "a substituent having two or more substituents connected" may be a biphenylyl group. That is, the biphenylyl group may be an aryl group, and may be interpreted as a substituent having two phenyl groups connected. For example, the term "substituted or unsubstituted" may be understood to mean "unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, C _1-10 alkyl, C _1-10 alkoxy, and C _6-20 aryl." In addition, the term "substituted with one or more substituents" in the present specification may be understood to mean, for example, "substituted with 1 to 5 substituents", or "substituted with 1 or 2 substituents."

In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a substituent having the following structure, but is not limited thereto.

In the present specification, the ester group may have the oxygen of the ester group substituted with a straight-chain, branched-chain, or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the substituent may have the following structural formula, but is not limited thereto.

In this specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a substituent having the following structure, but is not limited thereto.

In the present specification, a substituted or unsubstituted silyl group means -Si(Z ₁ )(Z ₂ )(Z ₃ ), wherein Z ₁ , Z ₂ and Z ₃ can each independently be hydrogen, deuterium, a substituted or unsubstituted C _1-60 alkyl, a substituted or unsubstituted C _1-60 haloalkyl, a substituted or unsubstituted C _2-60 alkenyl, a substituted or unsubstituted C _2-60 haloalkenyl, or a substituted or unsubstituted C _6-60 aryl. According to one embodiment, Z ₁ , Z ₂ and Z ₃ can each independently be hydrogen, deuterium, a substituted or unsubstituted C _1-10 alkyl, a substituted or unsubstituted C _1-10 haloalkyl, a substituted or unsubstituted C _1-10 haloalkyl, or a substituted or unsubstituted C _6-20 aryl. Specific examples of the above silyl group include, but are not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group.

In this specification, the boron group specifically includes, but is not limited to, a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, etc.

In this specification, examples of halogen groups include fluoro, chloro, bromo, or iodo.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to another embodiment, specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethyl-propyl, 1,1-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, isohexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, Examples include, but are not limited to, 1-methylheptyl, 2-ethylhexyl, 2,4,4-trimethyl-1-pentyl, 2,4,4-trimethyl-2-pentyl, 2-propylpentyl, n-nonyl, and 2,2-dimethylheptyl.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms in the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 6. Specific examples include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl, and styrenyl.

In the present specification, the alicyclic group refers to a substituent derived from a saturated or unsaturated hydrocarbon ring compound that contains only carbon as a ring-forming atom and does not have aromaticity, and is understood to encompass both monocyclic and condensed polycyclic compounds. According to one embodiment, the alicyclic group has 3 to 60 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. Examples of such alicyclic groups include a monocyclic group such as a cycloalkyl group, a bridged hydrocarbon group, a spiro hydrocarbon group, a substituent derived from a hydrogenated derivative of an aromatic hydrocarbon compound, and the like.

Specifically, examples of the cycloalkyl group include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc.

In addition, examples of the hydrocarbon group spanning the bridge include, but are not limited to, bicyclo[1.1.0]butyl, bicyclo[2.2.1]heptyl, bicyclo[4.2.0]octa-1,3,5-trienyl, adamantyl, and decalinyl.

In addition, examples of the above spiro ring hydrocarbon group include, but are not limited to, spiro[3.4]octyl and spiro[5.5]undecanyl.

In addition, the substituent derived from the hydrogenated derivative of the aromatic hydrocarbon compound means a substituent derived from a compound in which hydrogen is added to a part of an unsaturated bond of a monocyclic or polycyclic aromatic hydrocarbon compound, and examples of such substituents include, but are not limited to, 1 H -indenyl, 2 H -indenyl, 4 H -indenyl, 2,3-dihydro-1 H -indenyl, 1,4-dihydronaphthalenyl, 1,2,3,4-tetrahydronaphthalenyl, 6,7,8,9 - tetrahydro-5 H -benzo[7]annulenyl, 6,7-dihydro-5 H -benzocycloheptenyl, etc.

In the present specification, an aryl group is understood to mean a substituent derived from a monocyclic or condensed polycyclic compound having aromaticity and containing only carbon as a ring-forming atom, and the carbon number is not particularly limited, but is preferably 6 to 60 carbon atoms. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenylyl group, a terphenylyl group, or the like, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, or the like, but is not limited thereto.

In the present specification, a heterocyclic group refers to a substituent derived from a monocyclic or condensed polycyclic compound that further includes one or more heteroatoms selected from O, N, Si, and S in addition to carbon as a ring-forming atom, and is understood to encompass both a substituent having aromaticity and a substituent having no aromaticity. According to one embodiment, the heterocyclic group has 2 to 60 carbon atoms. According to another embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to another embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of such heterocyclic groups include a heteroaryl group, a substituent derived from a hydrogenated derivative of a heteroaromatic compound, and the like.

Specifically, the heteroaryl group refers to a substituent derived from a monocyclic or condensed polycyclic compound that further includes one or more heteroatoms selected from N, O, and S in addition to carbon as a ring-forming atom, and refers to a substituent having aromaticity. According to one embodiment, the heterocyclic group has 2 to 60 carbon atoms. According to another embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to another embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of the above heteroaryl group include a thiophenyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridinyl group, a bipyridinyl group, a pyrimidinyl group, a triazinyl group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, an isoquinolinyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzoimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzofuranyl group, a dibenzofuranyl group, a phenanthrolinyl group, Examples thereof include, but are not limited to, isoxazolyl group, thiadiazolyl group, and phenothiazinyl group.

In addition, the substituent derived from the hydrogenated derivative of the heteroaromatic compound refers to a substituent derived from a compound in which hydrogen is added to a part of an unsaturated bond of a monocyclic or polycyclic heteroaromatic compound, and examples of such a substituent include, but are not limited to, 1,3-dihydroisobenzofuranyl, 2,3-dihydrobenzofuranyl, 1,3-dihydrobenzo [c ] thiophenyl, 2,3-dihydro[b ] thiophenyl, etc.

In this specification, the aryl group among the aralkyl group, the aralkenyl group, the alkylaryl group, the arylamine group, and the arylsilyl group is the same as the examples of the aryl group described above. In this specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the examples of the alkyl group described above. In this specification, the heteroaryl among the heteroarylamine may be applied to the description of the heteroaryl described above. In this specification, the alkenyl group among the aralkenyl group is the same as the examples of the alkenyl group described above. In this specification, the description of the aryl group described above may be applied to the arylene except that it is a divalent group. In this specification, the description of the heteroaryl group described above may be applied to the heteroarylene except that it is a divalent group. In this specification, the description of the aryl group or the cycloalkyl group described above may be applied to the hydrocarbon ring except that it is not a monovalent group but is formed by combining two substituents. In this specification, the description of the above-mentioned heteroaryl may be applied, except that the heterocycle is not monovalent and is formed by combining two substituents.

As used herein, the term "deuterated or substituted with deuterium" means that at least one of the substitutable hydrogens in the compound, divalent linking group or monovalent substituent is replaced with deuterium.

Additionally, the term "unsubstituted or substituted with deuterium" or "substituted or unsubstituted with deuterium" means "unsubstituted or substituted with one to a maximum of nine hydrogen atoms." For example, the term "unsubstituted or substituted with deuterium phenanthryl" can be understood to mean "unsubstituted or substituted with nine deuterium atoms," considering that the maximum number of hydrogen atoms that can be substituted with deuterium in the phenanthryl structure is nine.

Additionally, the term "deuterated structure" encompasses compounds of all structures in which at least one hydrogen is replaced by a deuterium, divalent linking group, or monovalent substituent. For example, the deuterated structure of phenyl can be understood to refer to monovalent substituents of all structures in which at least one substitutable hydrogen in the phenyl group is replaced by a deuterium, as follows.

Additionally, the "deuterium substitution rate" or "deuteration degree" of a compound means the ratio of the number of substituted deuteriums to the total number of hydrogens that can exist in the compound (the sum of the number of hydrogens replaceable with deuterium in the compound and the number of substituted deuteriums) calculated as a percentage. Therefore, when the "deuterium substitution rate" or "deuteration degree" of a compound is "K%," it means that K% of the hydrogens replaceable with deuterium in the compound have been replaced with deuterium.

At this time, the "deuterium substitution rate" or "deuteration degree" can be measured according to a commonly known method using MALDI-TOF MS (Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometer), nuclear magnetic resonance spectroscopy ( ¹ H NMR), TLC/MS (Thin-Layer Chromatography/Mass Spectrometry), or GC/MS (Gas Chromatography/Mass Spectrometry). More specifically, when MALDI-TOF MS is used, the "deuterium substitution rate" or "deuteration degree" can be obtained by obtaining the number of substituted deuterium atoms in the compound through MALDI-TOF MS analysis, and then calculating the ratio of the number of substituted deuterium atoms to the total number of hydrogen atoms that may exist in the compound as a percentage.

(compound)

Meanwhile, the present invention provides a compound represented by the chemical formula 1.

Specifically, the compound represented by the above chemical formula 1 is a compound in which two pyriminine or triazine rings are connected by an (arylene)-(pyridine-2,6-diyl)-(arylene) linker structure, and is characterized in that the two pyriminine or triazine rings are identical to each other. The compound represented by the above chemical formula 1 having such a structure may exhibit superior thermal stability compared to a compound having a pyridinediyl linker structure but having a different connection position from the present compound. In addition, the compound represented by the above chemical formula 1 may have HOMO and LUMO energy levels suitable as an electron transport layer compared to a compound having a heterocyclic group other than a pyriminine or triazine ring.

Accordingly, an organic light-emitting device employing the compound can exhibit a lower driving voltage than an organic light-emitting device employing a compound having a different structure, and its efficiency and lifespan characteristics can be improved simultaneously.

Meanwhile, in the above chemical formula 1, HAr is a substituted or unsubstituted pyrimidinyl; or a substituted or unsubstituted triazinyl.

For example, the substituent of HAr can be any one selected from the group consisting of deuterium; cyano; halogen; substituted or unsubstituted C _1-60 alkyl; substituted or unsubstituted C _2-60 alkenyl; substituted or unsubstituted C _3-60 cycloalkyl; substituted or unsubstituted C _6-60 aryl; and substituted or unsubstituted C _2-20 heteroaryl containing 1 to 3 heteroatoms selected from N, O and S.

In addition, the term "substituted or unsubstituted" in the definition of the substituent of the above HAr may mean "unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, cyano, C _1-10 alkyl substituted or unsubstituted with deuterium, C _3-20 cycloalkyl substituted or unsubstituted with deuterium, C _6-20 aryl substituted or unsubstituted with deuterium, and C _2-20 heteroaryl containing 1 to 3 heteroatoms selected from N, O, and S substituted or unsubstituted with deuterium."

Additionally, when HAr is substituted, the number of substituents of HAr can be 1 to 3. Specifically, when HAr is pyrimidinyl, the number of substituents of HAr is 1, 2, or 3, and when HAr is triazinyl, the number of substituents of HAr is 1 or 2.

For example, the substituents of HAr are each independently C _1-10 alkyl; C _6-20 aryl; C _2-10 heteroaryl containing one heteroatom selected from N, O and S, and the substituents of HAr may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, cyano, C _1-10 alkyl substituted or unsubstituted with deuterium, C _3-20 cycloalkyl substituted or unsubstituted with deuterium, C _6-20 aryl substituted or unsubstituted with deuterium, and C _2-20 heteroaryl containing one to three heteroatoms selected from N, O and S substituted or unsubstituted with deuterium.

Specifically, for example, the substituents of HAr are each independently methyl, phenyl, biphenylyl, terphenylyl, naphthyl, pyridinyl, furanyl, or thiophenyl, and the substituents of HAr may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, cyano, C _1-10 alkyl substituted or unsubstituted with deuterium, C _3-20 cycloalkyl substituted or unsubstituted with deuterium, C _6-20 aryl substituted or unsubstituted with deuterium, and C _2-20 heteroaryl including 1 to 3 heteroatoms selected from N, O, and S substituted or unsubstituted with deuterium.

More specifically, for example, the substituents of HAr are each independently methyl, ethyl, propyl, phenyl, biphenylyl, terphenylyl, naphthyl, pyridinyl, furanyl, or thiophenyl, and the substituents of HAr may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, cyano, methyl substituted or unsubstituted with deuterium, and cyclohexyl substituted or unsubstituted with deuterium.

In one embodiment, when HAr has two substituents, the two substituents are the same;

When HAr has two substituents, the two substituents are different;

When HAr has three substituents, two of the three substituents are the same and the remaining one is different; or

If HAr has three substituents, all three substituents can be different.

In another embodiment, when two or more of the substituents of HAr are substituted or unsubstituted phenyl, at least one of the phenyls may be a substituted phenyl.

For example, if HAr is a substituted or unsubstituted triazinyl, and the substituent of the triazinyl group is a substituted or unsubstituted phenyl, at least one of the phenyls may be a substituted phenyl.

Here, "substituted phenyl" may mean phenyl substituted with one or more substituents selected from the group consisting of deuterium, cyano, C _1-10 alkyl substituted or unsubstituted with deuterium, C _3-20 cycloalkyl substituted or unsubstituted with deuterium, C _6-20 aryl substituted or unsubstituted with deuterium, and C _2-20 heteroaryl containing 1 to 3 heteroatoms selected from N, O, and S substituted or unsubstituted with deuterium.

In another embodiment, at least one of the substituents of HAr may be substituted with one or more deuterium atoms.

For example, at least one of the substituents of HAr can be phenyl substituted with 1 to 5 deuterium atoms.

In another embodiment, not all of the substituents of HAr may be unsubstituted phenyl.

In one embodiment, HAr can be any one of the substituents represented by the following formulae 2a to 2k:

In the above chemical formulas 2a to 2k,

R is hydrogen or deuterium,

Ar ₁ to Ar ₃ are each independently C _1-60 alkyl; C _6-60 aryl; or C _2-60 heteroaryl containing one or more heteroatoms selected from N, O, and S,

The above Ar ₁ to Ar ₃ may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, cyano, C _1-10 alkyl substituted or unsubstituted with deuterium, C _3-20 cycloalkyl substituted or unsubstituted with deuterium, C _6-20 aryl substituted or unsubstituted with deuterium, and C _2-20 heteroaryl containing 1 to 3 heteroatoms selected from N, O, and S substituted or unsubstituted with deuterium.

Specifically, Ar ₁ to Ar ₃ are each independently methyl, ethyl, propyl, phenyl, biphenylyl, terphenylyl, naphthyl, pyridinyl, furanyl, or thiophenyl,

The above Ar ₁ to Ar ₃ may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, cyano, C _1-10 alkyl substituted or unsubstituted with deuterium, C _3-20 cycloalkyl substituted or unsubstituted with deuterium, C _6-20 aryl substituted or unsubstituted with deuterium, and C _2-20 heteroaryl containing 1 to 3 heteroatoms selected from N, O, and S substituted or unsubstituted with deuterium.

More specifically, Ar ₁ to Ar ₃ are each independently methyl, ethyl, propyl, phenyl, biphenylyl, terphenylyl, naphthyl, pyridinyl, furanyl, or thiophenyl,

The above Ar ₁ to Ar ₃ may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, cyano, methyl substituted or unsubstituted with deuterium, and cyclohexyl substituted or unsubstituted with deuterium.

In one embodiment, in the formula 2a, 2b, 2c, 2d, 2e, or 2h, at least one of Ar ₁ and Ar ₂ is phenyl substituted with 1 to 5 deuteriums; or

In the above chemical formula 2i, 2j, or 2k, at least one of Ar ₁ to Ar ₃ may be phenyl substituted with 1 to 5 deuterium atoms.

In this way, a compound containing at least one deuterium atom within the compound has a stronger bond energy within the molecule than a compound that is not substituted with deuterium because the bond energy of the C-D bond is greater than the bond energy of the C-H bond, and thus, the material stability can be improved. Therefore, when the compound represented by the above chemical formula 1 contains deuterium, the efficiency and stability of the organic light-emitting device can be improved compared to a compound having a structure that is not substituted with deuterium.

In one embodiment, in the chemical formula 2a, 2b, 2c, 2d, 2e, or 2h, Ar ₁ and Ar ₂ may be the same as or different from each other.

In one embodiment, in the chemical formula 2i, 2j, or 2k, Ar ₁ to Ar ₃ may all be different.

In another embodiment, in the above formula 2i, 2j, or 2k, two of Ar ₁ , Ar ₂ and Ar ₃ may be the same as each other, and the remaining one may be different from them.

In one embodiment, HAr can be any one of the substituents represented by the above formulae 2b, 2c and 2j.

In another embodiment, in the above chemical formula 2h, both Ar ₁ and Ar ₂ may not be unsubstituted phenyl.

For example, HAr is selected from the group consisting of, but not limited to, one selected from the group consisting of:

.

Specifically, for example, HAr may be any one selected from the group consisting of:

.

Additionally, in one embodiment, L ₁ and L ₂ can be unsubstituted or deuterium substituted C _6-20 arylene.

In another embodiment, L ₁ and L ₂ are phenylene, biphenyldiyl, terphenyldiyl, naphthylene, anthracenylene, or phenanthrylene,

The above L ₁ and L ₂ may be unsubstituted or substituted with deuterium.

Specifically, L ₁ and L ₂ may each independently be any one selected from the group consisting of: and their deuterated structures:

.

Here, L ₁ and L ₂ may be the same or different.

Meanwhile, representative examples of compounds represented by the chemical formula 1 are as follows:

.

Meanwhile, the compound represented by the above chemical formula 1 can be manufactured by a manufacturing method such as the following reaction scheme 1, for example, when L ₁ and L ₂ are the same:

[Reaction Formula 1]

In the above reaction scheme 1, X is halogen, preferably bromo or chloro, and the description of the remaining substituents is as defined above.

Specifically, the compound represented by the above chemical formula 1 can be prepared by a Suzuki-coupling reaction of reactants A1 and A2. The Suzuki-coupling reaction is preferably performed in the presence of a palladium catalyst and a base, and the reactor for the reaction can be changed to a reactor known in the art. This preparation method will be further detailed in the preparation examples described below.

(organic light emitting device)

Meanwhile, the present invention provides an organic light-emitting device comprising a compound represented by the above chemical formula 1. For example, the present invention provides an organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound represented by the above chemical formula 1.

The organic layer of the organic light-emitting device of the present invention may be formed as a single layer structure, but may also be formed as a multilayer structure in which two or more organic layers are laminated. 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, an electron injection and transport layer, etc. as the organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

At this time, the organic layer containing the compound may be a hole blocking layer, an electron injection layer, an electron transport layer, or an electron injection and transport layer.

Specifically, the organic layer containing the compound may be an electron transport layer or an electron injection and transport layer.

In one embodiment, the organic layer may include a hole injection layer, a hole transport layer, a light-emitting layer, and an electron injection and transport layer, wherein the organic layer including the compound may be an electron injection and transport layer.

In another embodiment, the organic layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, and an electron injection and transport layer, wherein the organic layer including the compound may be an electron injection and transport layer.

In another embodiment, the organic layer may include a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer, a hole blocking layer, and an electron injection and transport layer, wherein the organic layer including the compound may be a hole blocking layer or an electron injection and transport layer.

In another embodiment, the organic layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, wherein the organic layer including the compound may be a hole blocking layer, an electron transport layer, or an electron injection layer.

The organic layer of the organic light-emitting device of the present invention may be formed as a single layer structure, but may be formed as a multilayer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure that further includes, in addition to the light-emitting layer as the organic layer, a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer between the light-emitting layer and the second electrode. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller or larger number of organic layers.

In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially laminated on a substrate, wherein the first electrode is an anode and the second electrode is a cathode. In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having a structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially laminated on a substrate, wherein the first electrode is a cathode and the second electrode is an anode. For example, the structure of an organic light-emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.

Figure 1 illustrates an example of an organic light-emitting device composed of a substrate (1), an anode (2), a hole transport layer (3), a light-emitting layer (4), an electron injection and transport layer (5), and a cathode (6). In this structure, the compound represented by the chemical formula 1 may be included in the hole transport layer.

Figure 2 illustrates an example of an organic light-emitting device composed of a substrate (1), an anode (2), a hole injection layer (7), a hole transport layer (3), an electron blocking layer (8), a light-emitting layer (4), a hole blocking layer (9), an electron injection and transport layer (5), and a cathode (6). In this structure, the compound represented by the chemical formula 1 may be included in the hole injection layer, the hole transport layer, or the electron blocking layer.

The organic light-emitting device according to the present invention can be manufactured using materials and methods known in the art, except that at least one of the organic layers includes a compound represented by the chemical formula 1. In addition, when the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

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

In addition, the compound represented by the above chemical formula 1 can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc.

In addition to this method, an organic light-emitting device can be manufactured by sequentially depositing an organic layer and an anode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited to this.

For example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

As the anode material, a material having a high work function is generally preferred so that hole injection into the organic layer can be facilitated. Specific examples of the anode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline.

The cathode material is preferably a material having a low work function to facilitate electron injection into the organic layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered materials such as LiF/Al or LiO ₂ /Al.

The above-mentioned hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, has an excellent hole injection effect at the anode, an excellent hole injection effect for the light-emitting layer or the light-emitting material, prevents the movement of excitons generated in the light-emitting layer to the electron injection layer or the electron injection material, and has excellent thin film forming ability. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include, but are not limited to, metal porphyrins, oligothiophenes, arylamine-based organic compounds, hexanitrilehexaazatriphenylene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinones, and conductive polymers such as polyaniline and polythiophene.

The above hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. As the hole transport material, a material having high hole mobility is suitable, which can transport holes from the anode or the hole injection layer and transfer them to the light-emitting layer. The hole transport material may include, but is not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having both a conjugated portion and a non-conjugated portion.

The above electron blocking layer is formed on the hole transport layer, preferably in contact with the light emitting layer, and refers to a layer that controls hole mobility, prevents excessive movement of electrons, and increases the probability of hole-electron coupling, thereby improving the efficiency of the organic light emitting device. The electron blocking layer includes an electron blocking material, and examples of such an electron blocking material include, but are not limited to, an arylamine-based organic material.

The above-mentioned light-emitting material is a material that can emit light in the visible light range by transporting holes and electrons from a hole transport layer and an electron transport layer, respectively, and combining them, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole series compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; benzoxazole, benzthiazole, and benzimidazole series compounds; poly(p-phenylenevinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc.

The above-described light-emitting layer may include a host material and a dopant material. As such a host material, a fused aromatic ring derivative or a heterocyclic compound may be used. Specifically, examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene derivatives, fluoranthene derivatives, etc., and examples of heterocyclic compound include, but are not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan derivatives, pyrimidine derivatives, etc.

Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periflanthene having an arylamino group, and styrylamine compounds include compounds in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, and wherein one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, and styryltetraamine, but are not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

The above hole blocking layer refers to a layer formed on a light-emitting layer, preferably provided in contact with the light-emitting layer, and serves to improve the efficiency of an organic light-emitting device by controlling electron mobility and preventing excessive movement of holes to increase the probability of hole-electron coupling. The hole blocking layer includes a hole blocking material, and examples of such hole blocking materials include compounds having an electron-withdrawing group introduced therein, such as azine derivatives including triazine; triazole derivatives; oxadiazole derivatives; phenanthroline derivatives; and phosphine oxide derivatives, but are not limited thereto.

The electron injection and transport layer is a layer that simultaneously functions as an electron transport layer and an electron injection layer that injects electrons from an electrode and transports the received electrons to the light-emitting layer, and is formed on the light-emitting layer or the hole blocking layer. As the electron injection and transport material, a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is suitable. The compound represented by the above chemical formula 1 can be used as the electron injection and transport layer material. Examples of additional electron injection and transport materials include, but are not limited to, an Al complex of 8-hydroxyquinoline; a complex containing Alq ₃ ; an organic radical compound; a hydroxyflavone-metal complex; and a triazine derivative. Alternatively, it may be used with, but is not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and their derivatives, metal complex compounds, or nitrogen-containing 5-membered ring derivatives.

The above electron injection and transport layer may also be formed as separate layers, such as an electron injection layer and an electron transport layer. In this case, the electron transport layer is formed on the light-emitting layer or the hole blocking layer, and the electron injection and transport material described above may be used as the electron transport material included in the electron injection layer. In addition, the electron injection layer is formed on the electron transport layer, and the electron injection material included in the electron injection layer may be LiF, NaCl, CsF, Li ₂ O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and the like, their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

The above metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, Bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc., but are not limited thereto.

The organic light-emitting device according to the present invention may be a bottom emission device, a top emission device, or a double-sided emission device, and in particular, may be a bottom emission device requiring relatively high luminous efficiency.

In addition, the compound represented by the above chemical formula 1 can be included in an organic solar cell or organic transistor in addition to an organic light-emitting device.

The manufacture of the compound represented by the above chemical formula 1 and the organic light-emitting device containing the same is specifically described in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited by them.

[Synthesis example]

Synthesis Example 1: Preparation of Compound E1

In a nitrogen atmosphere, E1-A (20 g, 84.4 mmol) and E1-B (73.6 g, 168.8 mmol) were added to 400 ml of tetrahydrofuran, stirred, and refluxed. Then, potassium carbonate (35 g, 253.3 mmol) dissolved in 35 ml of water was added, and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (2.9 g, 2.5 mmol) was added. After 1 hour of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was added again to 1172 ml of chloroform, dissolved, and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound E1 (36.9 g, 63%).

MS: [M+H] ⁺ = 694

Synthesis Example 2: Preparation of Compound E2

Compound E2 was prepared in the same manner as in Synthesis Example 1, except that each starting material was changed to the starting material of the above reaction formula.

MS: [M+H] ⁺ = 694

Synthesis Example 3: Preparation of Compound E3

Compound E3 was prepared in the same manner as in Synthesis Example 1, except that each starting material was changed to the starting material of the above reaction formula.

MS: [M+H] ⁺ = 696

Synthesis Example 4: Preparation of Compound E4

Compound E4 was prepared in the same manner as in Synthesis Example 1, except that each starting material was changed to the starting material of the above reaction formula.

MS: [M+H] ⁺ = 674

Synthesis Example 5: Preparation of Compound E5

Compound E5 was prepared in the same manner as in Synthesis Example 1, except that each starting material was changed to the starting material of the above reaction scheme.

MS: [M+H] ⁺ = 794

Synthesis Example 6: Preparation of Compound E6

Compound E6 was prepared in the same manner as in Synthesis Example 1, except that each starting material was changed to the starting material of the above reaction formula.

MS: [M+H] ⁺ = 744

Synthesis Example 7: Preparation of Compound E7

Compound E7 was prepared in the same manner as in Synthetic Example 1, except that each starting material was changed to the starting material of the above reaction formula.

MS: [M+H] ⁺ = 844

Synthesis Example 8: Preparation of Compound E8

Compound E8 was prepared in the same manner as in Synthesis Example 1, except that each starting material was changed to the starting material of the above reaction formula.

MS: [M+H] ⁺ = 694

Synthesis Example 9: Preparation of Compound E9

Compound E9 was prepared in the same manner as in Synthesis Example 1, except that each starting material was changed to the starting material of the above reaction formula.

MS: [M+H] ⁺ = 856

Synthesis Example 10: Preparation of Compound E10

In a nitrogen atmosphere, E10-A (20 g, 43.1 mmol) and E10-B (18.7 g, 43.1 mmol) were added to 400 ml of tetrahydrofuran, stirred, and refluxed. Then, potassium carbonate (17.9 g, 129.2 mmol) dissolved in 18 ml of water was added, and the mixture was stirred well before tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was added again to 596 ml of chloroform, dissolved, and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound E10 (22.3 g, 75%).

MS: [M+H] ⁺ = 692

Synthesis Example 11: Preparation of Compound E11

Compound E11 was prepared in the same manner as in Synthesis Example 1, except that each starting material was changed to the starting material of the above reaction formula.

MS: [M+H] ⁺ = 444

Synthesis Example 12: Preparation of Compound E12

Compound E12 was prepared in the same manner as in Synthesis Example 1, except that each starting material was changed to the starting material of the above reaction formula.

MS: [M+H] ⁺ = 714

Synthesis Example 13: Preparation of Compound E13

Compound E13 was prepared in the same manner as in Synthesis Example 1, except that each starting material was changed to the starting material of the above reaction formula.

MS: [M+H] ⁺ = 704

[Example]

Example 1

A glass substrate coated with a 1,000 Å thick ITO (indium tin oxide) film was placed in distilled water containing detergent and ultrasonically cleaned. The detergent was a Fischer Co. product, and the distilled water was secondarily filtered through a Millipore Co. filter. After washing the ITO for 30 minutes, ultrasonically cleaned twice with distilled water for 10 minutes each. After washing with distilled water, ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma and then transferred to a vacuum deposition machine.

A hole injection layer was formed by thermal vacuum deposition of the following compound HI-A to a thickness of 600 Å on the ITO transparent electrode prepared in this manner. A hole transport layer was formed by sequentially vacuum depositing the following compound HAT's hexanitrile hexaazatriphenylene (50 Å) and the following compound HT-A (600 Å) on the hole injection layer.

Next, a light-emitting layer was formed by vacuum-depositing the following compounds BH and BD at a weight ratio of 25:1 to a film thickness of 200 Å on the hole transport layer.

On the above-mentioned light-emitting layer, the compound E1 prepared in Synthesis Example 1 and the compound [LiQ] (Lithium quinolate) below were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 360 Å. On the above-mentioned electron injection and transport layer, lithium fluoride (LiF) was sequentially deposited with a thickness of 10 Å and aluminum was sequentially deposited with a thickness of 1,000 Å to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å/sec, the lithium fluoride of the cathode was maintained at 0.3 Å/sec, and the aluminum was maintained at 2 Å/sec. The vacuum during deposition was maintained at 1 * 10 ^-7 to 5 * 10 ^-8 torr, thereby manufacturing an organic light-emitting device.

Examples 2 to 13

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound described in Table 1 below was used instead of compound E1 as the electron injection and transport layer material in Example 1.

The structures of compounds E1 to E13 used in Examples 1 to 13 are summarized as follows.

Comparative Examples 1 to 6

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds described in Table 1 below were used instead of compound E1 as the electron injection and transport layer material in Example 1. Here, the structures of the compounds ET-1 to ET-6 are as follows.

Experimental Example 1: Evaluation of Device Characteristics

For the organic light-emitting devices manufactured in the above examples and comparative examples, the driving voltage, luminous efficiency and color coordinates were measured at a current density of 10 mA/cm ² and at a current density of 20 mA/cm ^{2 .} The time (T ₉₀ ) required for the current density to reach 90% of the initial luminance was measured. The results are shown in Table 1 below.

compound
(electron injection and transport layer) voltage
(V
@10mA/cm ² ) Efficiency
(cd/A
@10mA/cm ² ) Color coordinates
(x,y) T ₉₀
(hr
@20mA/cm ² ) Example 1 E1 5.11 3.88 (0.136, 0.112) 113 Example 2 E2 5.01 4.00 (0.136, 0.111) 90 Example 3 E3 5.06 3.96 (0.136, 0.112) 124 Example 4 E4 5.01 3.94 (0.136, 0.111) 120 Example 5 E5 5.16 3.92 (0.136, 0.111) 107 Example 6 E6 5.37 3.69 (0.136, 0.111) 147 Example 7 E7 5.06 3.84 (0.136, 0.112) 102 Example 8 E8 5.06 3.98 (0.136, 0.111) 110 Example 9 E9 5.17 3.93 (0.136, 0.112) 104 Example 10 E10 5.26 3.96 (0.136, 0.111) 116 Example 11 E11 5.42 3.80 (0.136, 0.111) 129 Example 12 E12 5.01 4.01 (0.136, 0.111) 100 Example 13 E13 5.06 3.97 (0.136, 0.112) 136 Comparative Example 1 ET-1 5.72 3.10 (0.136, 0.111) 45 Comparative Example 2 ET-2 5.78 3.04 (0.136, 0.111) 46 Comparative Example 3 ET-3 6.01 1.86 (0.136, 0.112) 23 Comparative Example 4 ET-4 6.07 1.83 (0.136, 0.111) 23 Comparative Example 5 ET-5 5.52 3.49 (0.136, 0.112) 23 Comparative Example 6 ET-6 5.41 3.60 (0.136, 0.111) 18

As shown in Table 1 above, it can be seen that the organic light-emitting device of the example using the compound represented by the chemical formula 1 as the electron injection and transport layer material exhibits significantly improved lifespan characteristics without a decrease in efficiency compared to the organic light-emitting device of the comparative example using a compound having a different structure.

Specifically, when comparing the organic light-emitting devices of Examples 1 to 13 of Table 1 with the organic light-emitting devices of Comparative Examples 1 to 4, it can be confirmed that the organic light-emitting device comprising the compound of Chemical Formula 1 of the present invention as an electron transport material exhibits significantly superior characteristics in terms of efficiency and lifespan compared to the organic light-emitting device using a compound including a heteroaryl moiety other than a triazinyl or pyrimidinyl group as a substituent connecting to the arylene linker.

In addition, when comparing the organic light-emitting devices of Examples 1 to 13 of Table 1 with the organic light-emitting devices of Comparative Examples 5 and 6, it was confirmed that the organic light-emitting device comprising the compound of Chemical Formula 1 of the present invention as an electron transport material had a pyridinediyl linker structure but showed significantly superior characteristics in terms of lifespan compared to the organic light-emitting device using a compound in which the arylene linker was connected to a position other than the pyridine 2 and 6 positions.

1: Substrate 2: Anode
3: Hole transport layer 4: Emissive layer
5: Electron injection and transport layer 6: Cathode
7: Hole injection layer 8: Electron blocking layer
9: The hole-blocking layer

Claims (12)

A compound represented by the following chemical formula 1:
[Chemical Formula 1]

In the above chemical formula 1,
HAr is pyrimidinyl; or triazinyl,
The HAr is unsubstituted or substituted with one or more substituents selected from the group consisting of C _1-10 alkyl substituted or unsubstituted with deuterium, cyano, C _3-20 cycloalkyl substituted or unsubstituted with deuterium, C _{6-20 aryl substituted or unsubstituted with deuterium, and C 2-20 heteroaryl} containing 1 to 3 heteroatoms selected from N, O and S substituted or unsubstituted with deuterium,
L ₁ and L ₂ are each independently phenylene, biphenyldiyl, terphenyldiyl, naphthylene, anthracenylene, or phenanthrylene, and L ₁ and L ₂ are unsubstituted or substituted with deuterium,
D stands for deuterium,
n is an integer from 0 to 3.
In the first paragraph,
When HAr has two substituents, the two substituents are the same;
When HAr has two substituents, the two substituents are different;
When HAr has three substituents, two of the three substituents are the same and the remaining one is different; or
If HAr has three substituents, all three substituents are different,
compound.
In the first paragraph,
HAr is any one of the substituents represented by the following chemical formulas 2a to 2k,
compound:


In the above chemical formulas 2a to 2k,
R is hydrogen or deuterium,
Ar ₁ to Ar ₃ are each independently C _1-60 alkyl; C _6-60 aryl; or C _2-60 heteroaryl containing one or more heteroatoms selected from N, O, and S,
The above Ar ₁ to Ar ₃ are unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, cyano, C _1-10 alkyl substituted or unsubstituted with deuterium, C _3-20 cycloalkyl substituted or unsubstituted with deuterium, C _6-20 aryl substituted or unsubstituted with deuterium, and C _2-20 heteroaryl containing 1 to 3 heteroatoms selected from N, O, and S substituted or unsubstituted with deuterium.
In the third paragraph,
Ar ₁ to Ar ₃ are each independently methyl, phenyl, biphenylyl, terphenylyl, naphthyl, pyridinyl, furanyl, or thiophenyl,
The above Ar ₁ to Ar ₃ are unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, cyano, methyl substituted or unsubstituted with deuterium, and cyclohexyl substituted or unsubstituted with deuterium.
compound.
In the third paragraph,
In the above chemical formula 2a, 2b, 2c, 2d, 2e, or 2h, at least one of Ar ₁ and Ar ₂ is phenyl substituted with 1 to 5 deuterium atoms; or
In the above chemical formula 2i, 2j, or 2k, at least one of Ar ₁ to Ar ₃ is phenyl substituted with 1 to 5 deuterium atoms,
compound.
In the first paragraph,
HAr is one selected from the group consisting of and their deuterated structures,
compound:


.
delete In the first paragraph,
L ₁ and L ₂ are each independently one selected from the group consisting of and their deuterated structures,
compound:


.
In the first paragraph,
L ₁ and L ₂ are identical or different,
compound.
In the first paragraph,
The above compound is any one selected from the group consisting of the following compounds:
compound:






.
An organic light-emitting device comprising: a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound according to any one of claims 1 to 6 and claims 8 to 10.
In Article 11,
The organic layer containing the above compound is an electron transport layer or an electron injection and transport layer.
Organic light emitting diode.