KR102206814B1 - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides a compound represented by Chemical Formula 1 and an organic light-emitting device including the same.

Description

Compound and organic light-emitting device comprising the same TECHNICAL FIELD

The present invention provides a compound represented by Formula 1 and an organic light-emitting device including the same.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer has a multilayer structure made of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls to the ground.

Development of a new material for the organic light emitting device as described above is continuously required.

Unexamined Patent Publication No. 10-2004-0049038

The present specification intends to provide an organic light-emitting device having a low driving voltage, high luminous efficiency, good lifespan, or high color purity by including the compound represented by Formula 1 in an organic light-emitting device.

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

[Formula 1]

In Formula 1,

Two adjacent ones of Y1 to Y4 are carbon atoms each bonded to two'*'s of the following formula D, and one of two of Y1 to Y4 not bonded to'*' of the following formula D is N, and the other is N or CR1,

[Formula D]

In Formula D,

X is O, S, Se, S(=O), NRm or CRmRn,

R1 to R3, Rm, Rn, Rx, Ry and Rz are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Alkyl group; Alkenyl group; Alkynyl group; Halogen group; Hydroxy group; Alkoxy group; Aryloxy group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Aryl group; Or a heteroaryl group, or deuterium by bonding with adjacent groups to each other; Alkyl group; Alkenyl group; Alkynyl group; Halogen group; Hydroxy group; Alkoxy group; Aryloxy group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Aryl group; And a heteroaryl group to form a substituted or unsubstituted ring with one or more substituents selected from the group consisting of,

a is an integer of 0 to 4, and when a is 2 or more, a plurality of R3s are the same as or different from each other.

An exemplary embodiment of the present specification is an organic light-emitting device comprising a first electrode, a second electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein the compound represented by Formula 1 is 1 It provides an organic light-emitting device that is included in one or more of the organic material layers of the layer or more.

In an exemplary embodiment of the present invention, when the compound represented by Formula 1 is included in the organic material layer of the organic light emitting device, particularly the light emitting layer, the efficiency of the device is improved, the driving voltage of the device is decreased, or the lifespan characteristics of the device are reduced. It can be improved.

1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, an organic material layer 3, and a cathode 4.
2 shows a substrate 1, an anode 2, a hole injection layer 5, a first hole transport layer 6, a second hole transport layer 7, a light emitting layer 8, an electron transport layer 9, and an electron injection layer. An example of an organic light-emitting device comprising (10) and a cathode (4) is shown.

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

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

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In this specification,

Means a site bonded to another substituent or a bonding portion.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent. The position at which the substituent is substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position at which the substituent can be substituted. When the above substituents are 2 or more, the 2 or more substituents may be the same or different from each other.

In the present specification, an alkyl group refers to a linear or branched saturated hydrocarbon. The number of carbon atoms in the alkyl group is not particularly limited, but is preferably 1 to 20. According to an exemplary embodiment, the alkyl group has 1 to 15 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. The alkyl group may be chain or cyclic.

Specific examples of the chain alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, n-pentyl, isopentyl , Neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc. Not limited.

The number of carbon atoms in the cyclic alkyl group (cycloalkyl group) is not particularly limited, but is preferably 3 to 20 carbon atoms. According to an exemplary embodiment, the cycloalkyl group has 3 to 16 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 12 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 8. Specific examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethyl Cyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the alkenyl group represents a hydrocarbon group having a carbon-carbon double bond, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. Specific examples of the alkenyl group include ethenyl, vinyl, propenyl, allyl, isopropenyl, butenyl, isobutenyl, n-pentenyl and n-hexenyl, but are not limited thereto.

In the present specification, the alkynyl group represents a hydrocarbon group having a carbon-carbon triple bond, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. According to an exemplary embodiment, the number of carbon atoms in the alkynyl group is 2 to 20. Specific examples of the alkynyl group include, but are not limited to, metaynyl, ethynyl, 2-propynyl, 2-butynyl, 1-methyl-2-butynyl, 2-pentynyl, and the like.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the alkoxy group refers to a group in which an alkyl group is bonded to an oxygen atom, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. According to an exemplary embodiment, the alkoxy group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkoxy group has 1 to 10 carbon atoms. Specific examples of the alkoxy group include, but are not limited to, methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, and hexyloxy. The description of the above-described alkyl group may be applied to the alkyl group of the alkoxy group.

In the present specification, an aryloxy group means a group in which an aryl group is bonded to an oxygen atom. Specific examples of the aryloxy group include, but are not limited to, phenoxy, 1-naphthyloxy, 3-methylphenoxy, and 4-methoxyphenoxy. Description of the aryl group described later may be applied to the aryl group of the aryloxy group.

In the present specification, the silyl group may be represented by the formula of -SiR ₁₁ R ₁₂ R ₁₃ , wherein R ₁₁ to R ₁₃ are each independently hydrogen; Alkyl group; Or it may be an aryl group. In the present specification, an alkylsilyl group refers to a silyl group substituted with an alkyl group, and an arylsilyl group refers to a silyl group substituted with an aryl group. Specifically, the silyl group includes trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, and the like, but is not limited thereto.

In the present specification, an aryl group means wholly or partially unsaturated substituted or unsubstituted monocyclic or polycyclic. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. Examples of the monocyclic aryl group include phenyl, biphenyl, and terphenyl, but are not limited thereto. Examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthrenyl, perylenyl, fluoranthenyl, triphenylenyl, phenalenyl, pyrenyl, tetracenyl, chrysenyl, pentacenyl, fluorenyl, indenyl, Acenaphthyl, benzofluorenyl, spirofluorenyl, and the like, but are not limited thereto.

In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

,

,

,

,

,

,

및

등이 있으나, 이에 한정되지 않는다.The substituted fluorenyl group is

,

,

,

,

,

,

And

And the like, but are not limited thereto.

In the present specification, the heteroaryl group is a cyclic group including at least one of N, O, and S as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40 carbon atoms. According to an exemplary embodiment, the heteroaryl group has 2 to 30 carbon atoms. According to another exemplary embodiment, the heteroaryl group has 2 to 20 carbon atoms. Examples of the heteroaryl group include thiophenyl, furanyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridinyl, bipyridinyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, Acenaphthoquinoxalinyl, indenoquinazolinyl, indenoisoquinolinyl, indenoquinolinyl, pyridoindole, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthala Genyl, pyrido pyrimidinyl, pyrido pyrazinyl, pyrazino pyrazinyl, isoquinolinyl, indolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzothiophenyl, dibenzothiophenyl, benzopyu Ranil, phenanthrolinyl, thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenoxazinyl, phenothiazinyl and dibenzofuranyl, etc., but limited to these no. The heteroaryl group includes an aliphatic heteroaryl group and an aromatic heteroaryl group.

In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the meaning of bonding with adjacent groups to form a ring means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic heterocycle; Or it means to form a condensed ring of these. The hydrocarbon ring refers to a ring consisting of only carbon and hydrogen atoms, and the hydrocarbon ring may be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle refers to a ring containing at least one heteroatom, and the heterocycle may be an aliphatic heterocycle or an aromatic heterocycle. In the present specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic hetero ring and aromatic hetero ring may be monocyclic or polycyclic.

The aliphatic hydrocarbon ring is a ring that is not aromatic and refers to a ring consisting only of carbon and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like, It is not limited to this.

The aromatic hydrocarbon ring refers to an aromatic ring consisting only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, benzo Fluorene, spirofluorene, and the like, but are not limited thereto.

The aliphatic heterocycle refers to an aliphatic ring containing one or more of heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxephan, azocaine , Thiocane, and the like, but are not limited thereto.

The aromatic heterocycle refers to an aromatic ring containing at least one heteroatom. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parasol, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thia Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinol, quinazoline, quinoxaline, naphthyridine, acridine , Phenanthridine, diazanaphthalene, dryazainden, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzo Carbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, phenanthridine, indolocarbazole, indenocarbazole, and the like, but are not limited thereto.

An exemplary embodiment of the present specification provides a compound represented by Chemical Formula 1.

In Formula 1, the adjacent two of Y1 to Y4 are Y1 and Y2; Y2 and Y3; Or it means Y3 and Y4.

In the exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; Or an alkyl group.

In the exemplary embodiment of the present specification, R1 is hydrogen; Or methyl.

In the exemplary embodiment of the present specification, R2 is hydrogen; Or an alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, R2 is hydrogen; Or an alkyl group having 1 to 8 carbon atoms.

In the exemplary embodiment of the present specification, R2 is hydrogen; Or an alkyl group having 1 to 6 carbon atoms.

In the exemplary embodiment of the present specification, R2 is hydrogen; Or methyl.

In an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; Or it is an alkyl group, or combines with an adjacent group to form a ring substituted or unsubstituted with one or more substituents of deuterium and an alkyl group.

In an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; Or an alkyl group having 1 to 10 carbon atoms, or combined with an adjacent group to form a benzene ring substituted or unsubstituted with one or more substituents among deuterium and an alkyl group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; Or an alkyl group having 1 to 6 carbon atoms, or combined with an adjacent group to form a benzene ring substituted or unsubstituted with at least one substituent among deuterium and an alkyl group having 1 to 6 carbon atoms.

In an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; methyl; Or t-butyl, or combine with adjacent groups to form a benzene ring.

In the exemplary embodiment of the present specification, a is 2.

In the exemplary embodiment of the present specification, a is 3.

In the exemplary embodiment of the present specification, Rm and Rn are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an alkyl group.

In the exemplary embodiment of the present specification, Rm and Rm are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an alkyl group having 1 to 6 carbon atoms.

In the exemplary embodiment of the present specification, Rm and Rn are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or it is a C1-C3 alkyl group.

In the exemplary embodiment of the present specification, Rm and Rn are the same as or different from each other, and each independently hydrogen; Or methyl.

In the exemplary embodiment of the present specification, Rx and Rz are the same as or different from each other, and each independently a linear or branched chain alkyl group having 1 to 10 carbon atoms; Or it is a C1-C10 cycloalkyl group.

In the exemplary embodiment of the present specification, Rx and Rz are the same as or different from each other, and each independently a linear or branched chain alkyl group having 1 to 8 carbon atoms; Or it is a C1-C8 cycloalkyl group.

In the exemplary embodiment of the present specification, Rx and Rz are the same as or different from each other, and each independently a linear or branched chain alkyl group having 1 to 6 carbon atoms; Or it is a C1-C6 cycloalkyl group.

In the exemplary embodiment of the present specification, Rx and Rz are the same as or different from each other, and each independently methyl; Isopropyl; 1-ethylpropyl; Or cyclohexyl.

In the exemplary embodiment of the present specification, Ry is hydrogen.

In an exemplary embodiment of the present specification, Formula 1 is represented by any one of the following Formulas 1-1 to 1-4.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formula 1-1,

Two adjacent ones of Y2 to Y4 are carbon atoms each bonded to two'*'s of the formula D, and one of Y2 to Y4 not bonded to'*' of the formula D is N or CR1,

In Formula 1-2,

Y3 and Y4 are each a carbon atom bonded to each of the two'*'s of Formula D, and Y1 is N or CR1,

In Formula 1-3,

Y1 and Y2 are each a carbon atom bonded to two'*'s of Formula D, respectively, Y4 is N or CR1,

In Formula 1-4,

Two adjacent ones of Y1 to Y3 are carbon atoms each bonded to two'*'s of Formula D, and one of Y1 to Y3 that does not bind to'*' of Formula D is N or CR1,

The definitions of R1, R3, Rx, Ry, Rz, and a are the same as those defined in Formula 1.

In the exemplary embodiment of Formula 1-1, in Y2 to Y4, an atom not bonded to'*' in Formula D is CR1.

In the exemplary embodiment of Formula 1-2, Y1 is CR1.

In the exemplary embodiment of Formula 1-3, Y4 is CR1.

In the exemplary embodiment of Formula 1-4, one of Y1 to Y3 that does not combine with'*' in Formula D is CR1.

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

[Formula 2-1]

[Formula 2-2]

In Formula 2-1 and Formula 2-2,

One of Y1 and Y2 is N, and the other is N or CR1,

The definitions of X, R1 to R3, Rx, Ry, Rz and a are as defined in Formula 1.

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

[Formula 3-1]

[Chemical Formula 3-2]

In Formula 3-1 and Formula 3-2,

One of Y1 and Y4 is N, and the other is N or CR1,

The definitions of X, R1 to R3, Rx, Ry, Rz and a are as defined in Formula 1.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 4-1 or Chemical Formula 4-2.

[Formula 4-1]

[Formula 4-2]

In Formula 4-1 and Formula 4-2,

One of Y3 and Y4 is N, the other is N or CR1,

The definitions of X, R1 to R3, Rx, Ry, Rz and a are as defined in Formula 1.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 5.

[Formula 5]

In Formula 5,

The definitions of Y1 to Y4, Rx, Ry and Rz are the same as defined in Formula 1,

R4 is hydrogen; heavy hydrogen; Alkyl group; Alkenyl group; Alkynyl group; Halogen group; Hydroxy group; Alkoxy group; Aryloxy group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Aryl group; Or a heteroaryl group,

b is an integer of 0 to 6, and when b is 2 or more, a plurality of R4s are the same as or different from each other.

In the exemplary embodiment of the present specification, R4 is hydrogen; heavy hydrogen; Or an alkyl group.

In the exemplary embodiment of the present specification, R4 is hydrogen; heavy hydrogen; Or an alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, R4 is hydrogen; heavy hydrogen; Or an alkyl group having 1 to 6 carbon atoms.

In the exemplary embodiment of the present specification, R4 is hydrogen; heavy hydrogen; methyl; Or t-butyl.

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

In an exemplary embodiment of the present specification, the compound represented by Formula 2-1 may be prepared according to the method of Formula 1 below.

[General Formula 1]

Formula 1 is an example of a method of forming a compound represented by Formula 2-1, and the method for synthesizing the compound represented by Formula 2-1 is not limited to Formula 1, and some synthesis steps are described in the art. It can be done by methods known in the field.

In Chemical Formula 2-1, when a main ligand having a different condensation position of the 5-membered ring and a different type of substituent is used, a compound represented by Chemical Formula 1 can be prepared.

The present specification provides an organic light-emitting device including the compound represented by Chemical Formula 1.

An exemplary embodiment of the present specification is an organic light emitting device including a first electrode, a second electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein the compound represented by Formula 1 is It provides an organic light-emitting device that is included in one or more of the one or more organic material layers.

The organic light emitting device of the present specification may include a single layer or a multilayer organic material layer between the first electrode and the second electrode. For example, the organic material layer included in the organic light emitting device of the present invention includes a hole injection layer, a hole transport layer, a layer that simultaneously transports and injects holes, a hole control layer, a light emitting layer, an electron control layer, an electron transport layer, an electron injection layer, and an electron transport layer. It may be one or more of the layers simultaneously injected.

In the exemplary embodiment of the present specification, the compound represented by Formula 1 is included in at least one layer of the at least one emission layer.

In the exemplary embodiment of the present specification, the emission layer including the compound represented by Formula 1 is a red emission layer.

In the exemplary embodiment of the present specification, when one or more emission layers are included in the organic light emitting device, each emission layer may exhibit a different color.

In the exemplary embodiment of the present specification, the organic light-emitting device including the compound represented by Formula 1 is a red organic light-emitting device.

In the exemplary embodiment of the present specification, the compound represented by Formula 1 is included in an amount of 1 part by weight or more and 10 parts by weight or less based on 100 parts by weight of the total light emitting layer including the compound.

In the exemplary embodiment of the present specification, the emission layer including the compound represented by Chemical Formula 1 further includes a host material.

In the exemplary embodiment of the present specification, the host material included in the light emitting layer including the compound represented by Formula 1 is a carbazole derivative compound or an aromatic polycyclic compound containing N.

In the exemplary embodiment of the present specification, the emission layer including the compound represented by Formula 1 further includes a host compound represented by the following Formula H.

[Formula H]

In the formula H,

G1 and G2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Alkyl group; Cycloalkyl group; Silyl group; Aryl group; Or a heteroaryl group, or combine with an adjacent group to form a ring,

G3 and G4 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group; Or an alkyl group, an aryl group, or a heteroaryl group unsubstituted or substituted with a heteroaryl group,

b1 is an integer from 0 to 7, and when b1 is 2 or more, a plurality of G1s are the same or different from each other,

b2 is an integer of 0 to 7, and when b2 is 2 or more, a plurality of G2s are the same or different from each other.

In the exemplary embodiment of the present specification, G1 is combined with an adjacent group to form a benzene ring.

In the exemplary embodiment of the present specification, G4 is a heteroaryl group that is unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group and includes N.

In the exemplary embodiment of the present specification, G4 is a heteroaryl group which is unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group and includes a 6-membered ring including N.

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

[Formula H-1]

In the formula H-1,

The definitions of G1 to G4 and b2 are the same as those defined in Formula H,

b3 is an integer of 0 to 9, and when b3 is 2 or more, a plurality of G1s are the same or different.

In an exemplary embodiment of the present specification, the compound represented by Formula H is the following compound.

In the exemplary embodiment of the present specification, the compound represented by Formula 1 is included in at least one of a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting holes, and a hole control layer.

In the exemplary embodiment of the present specification, the compound represented by Formula 1 is included in at least one of an electron injection layer, an electron transport layer, a layer that simultaneously injects and transports electrons, and an electron control layer.

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

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

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

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

The structure of the organic light-emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 and 2.

The organic light emitting device according to an exemplary embodiment of the present invention may include a substrate 1, an anode 2, an organic material layer 3, and a cathode 4, as shown in FIG. 1. In an exemplary embodiment, the compound represented by Formula 1 is included in the organic material layer (3).

The organic light emitting device according to an exemplary embodiment of the present invention includes a substrate 1, an anode 2, a hole injection layer 5, a first hole transport layer 6, and a second hole transport layer 7, as shown in FIG. 2. ), a light emitting layer 8, an electron transport layer 9, an electron injection layer 10, and a cathode 4. In an exemplary embodiment, the compound represented by Formula 1 is included in the light-emitting layer 8.

However, the structure of the organic light emitting device according to the exemplary embodiment of the present specification is not limited to FIGS. 1 and 2 and may be any one of the following structures.

(1) Anode/Hole Transport Layer/Light-Emitting Layer/Anode

(2) Anode/Hole Injection Layer/Hole Transport Layer/Light-Emitting Layer/Anode

(3) Anode/Hole Transport Layer/Light-Emitting Layer/Electron Transport Layer/Anode

(4) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

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

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

(7) Anode/hole transport layer/hole control layer/light-emitting layer/electron transport layer/cathode

(8) Anode/hole transport layer/hole control layer/light emitting layer/electron transport layer/electron injection layer/cathode

(9) Anode/hole injection layer/hole transport layer/hole control layer/light emitting layer/electron transport layer/cathode

(10) Anode/Hole injection layer/Hole transport layer/Hole control layer/Light emitting layer/Electron transport layer/Electron injection layer/Anode

(11) Anode/Hole Transport Layer/Light-Emitting Layer/Electron Control Layer/Electron Transport Layer/Anode

(12) Anode/hole transport layer/light emitting layer/electron control layer/electron transport layer/electron injection layer/cathode

(13) Anode/hole injection layer/hole transport layer/light emitting layer/electron control layer/electron transport layer/cathode

(14) Anode/hole injection layer/hole transport layer/light emitting layer/electron control layer/electron transport layer/electron injection layer/cathode

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

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

In addition, the compound represented by Formula 1 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, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

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

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

The hole injection layer is a layer for injecting holes received from an electrode into a light emitting layer or a layer adjacent to the light emitting layer. The hole injection material has the ability to transport holes and thus has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and transfer of excitons generated in the light emitting layer to the electron injection layer or the electron injection material. It is preferable to use a compound that prevents and has excellent thin film formation ability. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene There are a series of organic substances, anthraquinone, and polyaniline and a polythiophene series of conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer. The hole transport material is a material capable of transporting holes from an anode or a hole injection layer and transferring them to the emission layer, and a material having high mobility for holes is suitable. Specific examples of the hole transport material include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion.

The hole control layer is a layer that prevents the flow of electrons into the light emitting layer to the anode and controls the flow of holes flowing into the light emitting layer to control the performance of the entire device. The hole control material is preferably a compound having the ability to prevent the inflow of electrons from the light-emitting layer to the anode and to control the flow of holes injected into the light-emitting layer or the light-emitting material. In one embodiment, an arylamine-based organic material may be used as the electron blocking layer, but is not limited thereto.

The light-emitting material is a material capable of emitting light in a visible light region by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzothiazole and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The emission layer may include a host material and a dopant material.

The host material may be a condensed aromatic ring derivative or a heterocyclic-containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include dibenzofuran derivatives, ladder furan compounds, And pyrimidine derivatives, but are not limited thereto.

Examples of the dopant material for the light emitting layer include an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, and a metal complex. As the aromatic amine derivative, as a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, pyrene, anthracene, chrysene, periflanthene and the like having an arylamine group may be used. As the styrylamine compound, a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine may be used. Examples of the styrylamine compound include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. The metal complex may be an iridium complex or a platinum complex, but is not limited thereto.

The electron control layer is a layer that blocks the inflow of holes from the emission layer to the cathode and controls the electrons flowing into the emission layer to control the performance of the entire device. The electron controlling material is preferably a compound having the ability to prevent the inflow of holes from the light-emitting layer to the cathode and to control electrons injected into the light-emitting layer or the light-emitting material. As the electron controlling material, a suitable material may be used according to the configuration of the organic material layer used in the device. The electron control layer is located between the emission layer and the cathode, and is preferably provided in direct contact with the emission layer.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transport material, a material capable of receiving electrons well from the cathode and transferring them to the light emitting layer, and a material having high mobility for electrons is suitable. Examples of the electron transport material include Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired negative electrode material as used according to the prior art. In one embodiment, the negative electrode material is a material having a low work function; And an aluminum layer or a silver layer. Examples of the material having the low work function include cesium, barium, calcium, ytterbium, and samarium, and an aluminum layer or a silver layer may be formed on the layer after forming a layer with the material.

The electron injection layer is a layer for injecting electrons received from an electrode into the light emitting layer. The electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and transfer of excitons generated in the light emitting layer to the hole injection layer or the hole injection material In addition, it is preferable to use a compound having excellent thin film forming ability. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, benzimidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. Derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, 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. It is not limited to this.

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

Hereinafter, for a detailed understanding of the present invention, a method of manufacturing the compound of the present invention and an organic light-emitting device including the same will be described.

[Production Example]

Preparation Example 1: Synthesis of Compound 1

(1) Preparation of intermediate A1

In a nitrogen atmosphere, in a round bottom flask, 7-chloro-2-methyloxazolo[4,5-d]pyrimidine (50g, 0.3mol) and ( After dissolving 3,5-dimethylphenyl)boronic acid ((3,5-dimethylphenyl)boronic acid) (49g, 0.32mol) in THF 500ml, 2M potassium carbonate solution (200ml) was added, and tetrakis -(Triphenylphosphine)palladium (10g, 9mmol) was added, followed by heating and stirring at 70°C for 5 hours. After the reaction was completed, the temperature was lowered, the aqueous layer was separated, and the solvent in the organic layer was removed. After dissolving with chloroform, washing with water, magnesium sulfate and acid clay were added, stirred, filtered, and concentrated under reduced pressure. After this, intermediate A1 was prepared by column chromatography with hexane and ethyl acetate (20:1 volume ratio) (54g, 82% yield).

(2) Preparation of intermediate A2

In a nitrogen atmosphere, add iridium chloride (30g, 0.1mol) and intermediate A1 (54g, 0.26mol) to 1500ml of 2-ethoxyethanol and 500ml of distilled water in a round bottom flask at 130℃ for 24 hours It was heated and stirred at. The temperature was lowered to room temperature, filtered, and washed with 2L of ethanol to prepare a solid compound A2 (34.3g, yield 53%).

(3) Preparation of compound 1

After dissolving intermediate A2 (34.3 g, 0.03 mol), acetylacetone (7.5 g, 0.75 mol) and potassium carbonate (10 g, 0.75 mol) in 400 ml of 2-ethoxyethanol in a nitrogen atmosphere, 28 Heated and stirred at 50° C. for an hour. After completion of the reaction, the temperature was lowered to room temperature, filtered through celite, and the filtrate was concentrated under reduced pressure. Thereafter, compound 1 was prepared by purifying through column chromatography with dichloromethane and methanol (50:1 volume ratio). (18g, yield 43%, MS:[M+H] ⁺ = 712.8)

Preparation Example 2: Synthesis of Compound 2

Compound 1, except that 2,2,6,6-tetramethylheptane-3,5-dione (2,2,6,6-tetramethylheptane-3,5-dione) was used instead of acetylacetone Compound 2 was prepared in the same manner as in the method of preparing (yield 52%, MS: [M+H] ⁺ = 796.9).

Preparation Example 3: Synthesis of Compound 3

Except for the use of 3,7-diethylnonane-4,6-dione (3,7-diethylnonane-4,6-dione) instead of acetylacetone, the above Compound 3 was prepared. (Yield 50%, MS: [M+H] ⁺ = 825)

Preparation Example 4: Synthesis of Compound 4

(1) Preparation of intermediate A3

7-chloro-2-methyloxazolo[5, instead of 7-chloro-2-methyloxazolo[4,5-d]pyrimidine) in the flask Intermediate A3 was prepared in the same manner as for preparing compound 1 except for using 4-d]pyrimidine (7-chloro-2-methyloxazolo[5,4-d]pyrimidine) (45 g, 0.26 mol). .(56g, 90% yield)

(2) Preparation of intermediate A4

The intermediate A4 was prepared in the same manner as the method of preparing the intermediate A2, except that the intermediate A3 was used instead of the intermediate A1. (31g, yield 48%)

(3) Preparation of compound 4

Compound 4 was prepared in the same manner as for preparing compound 1, except that intermediate A4 was used instead of intermediate A2. (17g, yield 43%, MS: [M+H] ⁺ = 712.8)

Preparation Example 5: Synthesis of Compound 5

Compound 5 was prepared in the same manner as in the method of preparing compound 1, except that intermediate A4 instead of intermediate A2 and 2,2,6,6-tetramethylheptane-3,5-dione was used instead of acetylacetone. (11g, yield 57%, MS:[M+H] ⁺ = 796.9)

Preparation Example 6: Synthesis of Compound 6

Compound 6 was prepared in the same manner as in the method of preparing compound 1, except that intermediate A4 instead of intermediate A2 and 3,7-diethylnonane-4,6-dione was used instead of acetylacetone. (13 g, yield) 49%, MS:[M+H] ⁺ = 825)

Preparation Example 7: Synthesis of Compound 7

(1) Preparation of intermediate A5

3,4-dibromo-6-chloropyridazine (3,4-dibromo-6-chloropyridazine) (30 g, 0.26 mol) and acetamide (13 g, 0.29 mol) in a round bottom flask in a nitrogen atmosphere After dissolving triethylamine (52 g, 0.52 mol) in 500 ml of tetrahydrofuran, the mixture was stirred at room temperature for 8 hours. After completion of the reaction, 100 ml of 1M aqueous chloride chloride solution was poured for quenching, and an aqueous ammonium chloride solution was poured to separate the organic layer, followed by distillation under reduced pressure. After dissolving in 300 ml of chloroform, acid clay and MgSO ₄ were added, stirred, and filtered through Celite. The filtrate was distilled under reduced pressure, and then purified through column chromatography with hexane and ethyl acetate (25:1 volume ratio) to prepare an intermediate A5. (23g, yield 65%)

(2) Preparation of intermediate A6

A method for preparing intermediate A1 except that intermediate A5 was used instead of 7-chloro-2-methyloxazolo[4,5-d]pyrimidine, and The intermediate A6 was prepared in the same way. (28g, 73% yield)

(3) Preparation of intermediate A7

The intermediate A7 was prepared in the same manner as the method of preparing the intermediate A2, except for using the intermediate A6 instead of the intermediate A1. (31g, yield 48%)

(4) Preparation of compound 7

Compound 7 was prepared in the same manner as for preparing compound 1, except that intermediate A7 was used instead of intermediate A2. (15g, yield 41%, MS:[M+H] ⁺ = 712.8)

Preparation Example 8: Synthesis of Compound 8

Compound 8 was prepared in the same manner as in the method of preparing compound 1, except for using intermediate A7 instead of intermediate A2 and 2,2,6,6-tetramethylheptane-3,5-dione instead of acetylacetone. (19g, yield 58%, MS:[M+H] ⁺ = 796.9)

Preparation Example 9: Synthesis of Compound 9

Compound 9 was prepared in the same manner as in the method of preparing compound 1 except for using intermediate A7 instead of intermediate A2 and 3,7-diethylnonane-4,6-dione instead of acetylacetone. (10 g, yield) 48%, MS:[M+H] ⁺ = 825)

Preparation Example 10: Synthesis of Compound 10

(1) Preparation of intermediate A8

Intermediate A8 was prepared in the same manner as the method of preparing Intermediate A5, except that ethanethioamide was used instead of acetamide. (37g, yield 61%)

(2) Preparation of intermediate A9

A method for preparing intermediate A1, except that intermediate A8 was used instead of 7-chloro-2-methyloxazolo[4,5-d]pyrimidine, and The intermediate A9 was prepared in the same way. (51 g, 83% yield)

(3) Preparation of intermediate A10

The intermediate A10 was prepared in the same manner as the method of preparing the intermediate A2 except for using the intermediate A9 instead of the intermediate A1. (45g, yield 50%)

(4) Preparation of compound 10

Compound 10 was prepared in the same manner as for preparing compound 1, except that intermediate A10 was used instead of intermediate A2. (37g, yield 45%, MS: [M+H] ⁺ = 744.9)

Preparation Example 11: Synthesis of Compound 11

Compound 11 was prepared in the same manner as in the method of preparing compound 1 except for using intermediate A10 instead of intermediate A2 and 2,2,6,6-tetramethylheptane-3,5-dione instead of acetylacetone. (23g, yield 47%, MS:[M+H] ⁺ = 829)

Preparation Example 12: Synthesis of Compound 12

Compound 12 was prepared in the same manner as in the method of preparing compound 1 except for using intermediate A10 instead of intermediate A2 and 3,7-diethylnonane-4,6-dione instead of acetylacetone. (28 g, yield 52%, MS: [M+H] ⁺ = 857.1)

Preparation Example 13: Synthesis of Compound 13

(1) Preparation of intermediate A11

In the same manner as in the preparation of Intermediate A5, except that 2,3-dibromo-5-chloropyrazine (2,3-dibromo-5-chloropyrazine) was used instead of 3,4-dibromo-6-chloropyridazine. The intermediate A11 was prepared. (40 g, 63% yield).

(2) Preparation of intermediate A12

A method for preparing intermediate A1 except for using intermediate A11 instead of 7-chloro-2-methyloxazolo[4,5-d]pyrimidine The intermediate A12 was prepared in the same way. (56g, 73% yield)

(3) Preparation of intermediate A13

The intermediate A13 was prepared in the same manner as the method of preparing the intermediate A2 except for using the intermediate A12 instead of the intermediate A1. (33g, yield 46%)

(4) Preparation of compound 13

Compound 13 was prepared in the same manner as for preparing compound 1, except that intermediate A13 was used instead of intermediate A2. (25g, yield 41%, MS: [M+H] ⁺ = 712.8)

Preparation Example 14: Synthesis of Compound 14

Compound 14 was prepared in the same manner as in the method of preparing compound 1, except that intermediate A13 instead of intermediate A2 and 2,2,6,6-tetramethylheptane-3,5-dione was used instead of acetylacetone. (14g, yield 43%, MS:[M+H] ⁺ = 796.9)

Preparation Example 15: Synthesis of Compound 15

Compound 15 was prepared in the same manner as in the method of preparing compound 1, except for using intermediate A13 instead of intermediate A2 and 3,7-diethylnonane-4,6-dione instead of acetylacetone. (13 g, yield) 45%, MS:[M+H] ⁺ = 825)

Preparation Example 16: Synthesis of Compound 16

(1) Preparation of intermediate A16

Instead of 7-chloro-2-methyloxazolo[4,5-d]pyrimidine) Intermediate A5, instead of (3,5-dimethylphenyl)boronic acid Intermediate A16 was prepared in the same manner as in the method of preparing Intermediate A1, except that naphthalen-2-ylboronic acid was used. (36g, yield 88%)

(3) Preparation of intermediate A17

The intermediate A17 was prepared in the same manner as the method of preparing the intermediate A2, except that intermediate A16 was used instead of intermediate A1. (18g, yield 47%)

(4) Preparation of compound 16

Compound 16 was prepared in the same manner as for preparing compound 1, except that intermediate A17 was used instead of intermediate A2. (11g, yield 42%, MS: [M+H] ⁺ = 897)

Preparation Example 17: Synthesis of Compound 17

(1) Preparation of intermediate A18

Instead of 7-chloro-2-methyloxazolo[4,5-d]pyrimidine) Intermediate A5, instead of (3,5-dimethylphenyl)boronic acid Except for using (4-(t-butyl)naphthalen-2-yl)boronic acid ((4-(tert-butyl)naphthalene-2-yl)boronic acid), use the same method as the method of preparing Intermediate A1. Intermediate A18 was prepared. (42g, yield 77%)

(3) Preparation of intermediate A19

The intermediate A19 was prepared in the same manner as the method of preparing the intermediate A2, except that the intermediate A18 was used instead of the intermediate A1. (22g, yield 51%)

(4) Preparation of compound 17

Compound 17 was prepared in the same manner as for preparing compound 1, except that intermediate A19 was used instead of intermediate A2. (15g, yield 46%, MS: [M+H] ⁺ = 1009.3)

Preparation Example 18: Synthesis of Compound 18

(1) Preparation of intermediate A20

7-chloro-2-methylthiazolo[4,5-d]pyrimidine instead of 7-chloro-2-methyloxazolo[4,5-d]pyrimidine (7-chloro-2-methylthiazolo[4,5 -d]pyrimidine) (30g, 0.16mol), (4-(t-butyl)naphthalen-2-yl)boronic acid ((4-(tert-butyl)naphthalene-) instead of (3,5-dimethylphenyl)boronic acid Intermediate A20 was prepared in the same manner as in the method of preparing Intermediate A1 except for using 2-yl)boronic acid) (39g, yield 72%).

(3) Preparation of intermediate A21

The intermediate A21 was prepared in the same manner as the method of preparing the intermediate A2, except that the intermediate A20 was used instead of the intermediate A1. (24g, yield 50%)

(4) Preparation of compound 18

Compound 18 was prepared in the same manner as for preparing compound 1, except that intermediate A21 was used instead of intermediate A2. (13g, yield 43%, MS:[M+H] ⁺ = 957.3)

Example 1

A glass substrate (corning 7059 glass) coated with a thin film of ITO (indium tin oxide) to a thickness of 1,000 Å was placed in distilled water containing a dispersant and washed with ultrasonic waves. The detergent was manufactured by Fischer Co., and the distilled water was Millipore Co. Distilled water filtered secondarily with the product's filter was used. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying. On the prepared ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT-CN) was thermally vacuum deposited to a thickness of 50Å to form a hole injection layer. The following HT1 compound for transporting holes was vacuum-deposited thereon, followed by depositing the following HT2 compound to form first (700Å) and second hole transport layers (200Å). Next, the following H1 compound and compound 1 were vacuum-deposited to form a light emitting layer (300Å) so that 3 parts by weight of Compound 1 were included on the second hole transport layer based on 100 parts by weight of the total weight of the following H1 compound and compound 1. Then, the following E0 compound was sequentially thermally vacuum deposited (300Å) as an electron injection and transport layer. Lithium fluoride (LiF) having a thickness of 12 Å and aluminum having a thickness of 2,000 Å were sequentially deposited on the electron transport layer to form a cathode, and then an organic light emitting device was manufactured. In the above process, the deposition rate of organic material was maintained at 1 Å/sec, the deposition rate of LiF was 0.2 Å/sec, and the deposition rate of aluminum was maintained at 3 Å/sec to 7 Å/sec.

Examples 2 to 12

Organic light-emitting devices of Examples 2 to 12 were each manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 below were used instead of Compound 1 as a phosphorescent dopant when forming the emission layer.

Comparative Examples 1 to 3

Organic light-emitting devices of Comparative Examples 1 to 3 were each manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound 1 as a phosphorescent dopant when forming the emission layer.

Experimental Example 1

Voltage, efficiency, color coordinates and lifetime were measured by applying a current to the organic light emitting devices fabricated in Examples 1 to 12 and Comparative Examples 1 to 3, and the results are shown in Table 1 below.

T95 refers to the time it takes for the luminance to decrease to 95% from the initial luminance.

Dopant
matter λ _max
(nm) Voltage
(V
@10mA/cm ² ) efficiency
(cd/A
@10mA/cm ² ) Color coordinates
(x,y) life span
(T95, h,
@50mA/cm ² ) Example 1 One 626 4.0 34 (0.647, 0.345) 168 Example 2 2 626 4.2 32 (0.640, 0.330) 180 Example 3 3 625 4.2 31 (0.638, 0.328) 176 Example 4 4 627 4.0 33 (0.649, 0.347) 173 Example 5 7 630 3.8 35 (0.667, 0.331) 204 Example 6 8 632 3.9 38 (0.680, 0.325) 210 Example 7 9 630 4.3 36 (0.672, 0.327) 198 Example 8 10 628 4.3 36 (0.652, 0.350) 165 Example 9 11 628 4.2 35 (0.676, 0.319) 162 Example 10 13 628 4.1 32 (0.652, 0.330) 165 Example 11 17 627 4.1 37 (0.672, 0.320) 150 Example 12 18 630 4.0 38 (0.675, 0.323) 182 Comparative Example 1 E1 616 4.6 26 (0.632, 0.329) 98 Comparative Example 2 E2 621 4.8 24 (0.656, 0.313) 110 Comparative Example 3 E3 623 4.5 26 (0.678, 0.318) 115

As can be seen from the results of Table 1, the organic light emitting device using the compound of the present invention exhibits high purity red light emission and has low voltage, high efficiency, and long life characteristics. The LUMO energy level of the compound of the present invention is mainly distributed in a ring containing pyridazine, pyrimidine, or pyrazine of the main ligand. Since the main ligand of the compound of the present invention includes a structure including one or more nitrogen atoms with high electronegativity in the pyridine ring, the LUMO level is lower than that of the compound in which the main ligand contains pyridine. When the LUMO level of the dopant compound decreases, the energy band gap decreases, so that red light in a long wavelength region can be emitted. As a result, Examples 1 to 12 using the compounds of the present invention showed the maximum emission wavelength in a longer wavelength region than the dopants of the oxazolopyridine, cyanopyrimidine and cynopyrimidine structures of Comparative Examples 1 to 3. In addition, it showed a red wavelength with good color purity, while at the same time exhibiting high efficiency and long life. In the case of Example 6, compared to Comparative Example 1, the lifespan was increased by up to two times, and low driving voltage and high efficiency were maintained.

1: substrate
2: anode
3: organic material layer
4: cathode
5: hole injection layer
6: first hole transport layer
7: second hole transport layer
8: light emitting layer
9: electron transport layer
10: electron injection layer

Claims (12)

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

In Formula 1,
Two adjacent ones of Y1 to Y4 are carbon atoms each bonded to two'*'s of the following formula D, and one of two of Y1 to Y4 not bonded to'*' of the following formula D is N, and the other is CR1,
[Formula D]

In Formula D,
X is O, S or Se,
R1 and Ry are the same as or different from each other, and each independently hydrogen or deuterium,
R2 is a chain alkyl group,
Rx and Rz are the same as or different from each other, and each independently a chain alkyl group or a cycloalkyl group,
R3 is hydrogen, deuterium or a chain alkyl group, or is bonded to each other with adjacent groups to form a benzene ring,
a is an integer of 0 to 4, and when a is 2 or more, a plurality of R3s are the same as or different from each other. The compound of claim 1, wherein the formula 1 is represented by any one of the following formulas 1-1 to 1-4:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formula 1-1,
Two adjacent ones of Y2 to Y4 are carbon atoms each bonded to two'*'s of the formula D, and one of Y2 to Y4 not bonded to the'*' of the formula D is CR1,
In Formula 1-2,
Y3 and Y4 are each a carbon atom bonded to each of the two'*'s of Formula D, and Y1 is CR1,
In Formula 1-3,
Y1 and Y2 are each a carbon atom bonded to the two'*'s of Formula D, and Y4 is CR1,
In Formula 1-4,
Two adjacent ones of Y1 to Y3 are carbon atoms each bonded to two'*'s of Formula D, and one of Y1 to Y3 that does not bind to'*' of Formula D is CR1,
The definitions of R1, R3, Rx, Ry, Rz, and a are the same as those defined in Formula 1. The compound of claim 1, wherein the formula 1 is represented by the following formula 2-1 or 2-2:
[Formula 2-1]

[Formula 2-2]

In Formula 2-1 and Formula 2-2,
One of Y1 and Y2 is N, the other is CR1,
The definitions of X, R1 to R3, Rx, Ry, Rz and a are as defined in Formula 1. The compound according to claim 1, wherein Formula 1 is represented by the following Formula 3-1 or Formula 3-2:
[Formula 3-1]

[Chemical Formula 3-2]

In Formula 3-1 and Formula 3-2,
One of Y1 and Y4 is N, the other is CR1,
The definitions of X, R1 to R3, Rx, Ry, Rz and a are as defined in Formula 1. The compound of claim 1, wherein the formula 1 is represented by the following formula 4-1 or formula 4-2:
[Formula 4-1]

[Formula 4-2]

In Formula 4-1 and Formula 4-2,
One of Y3 and Y4 is N, the other is CR1,
The definitions of X, R1 to R3, Rx, Ry, Rz and a are as defined in Formula 1. The compound of claim 1, wherein Formula 1 is represented by the following Formula 5:
[Formula 5]

In Formula 5,
The definitions of Y1 to Y4, Rx, Ry and Rz are the same as defined in Formula 1,
R4 is hydrogen,
b is an integer from 0 to 6. The compound of claim 1, wherein the compound represented by Formula 1 is any one selected from the following compounds:

. An organic light-emitting device comprising a first electrode, a second electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein the compound according to any one of claims 1 to 7 is An organic light emitting device that is included in at least one of the organic material layers. The organic light-emitting device of claim 8, wherein the organic material layer includes at least one emission layer, and the compound represented by Formula 1 is included in at least one layer of the at least one emission layer. The organic light-emitting device of claim 9, wherein the light-emitting layer including the compound represented by Formula 1 is a red light-emitting layer. The method according to claim 8, wherein the organic material layer comprises at least one of a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting holes, and a hole control layer, and the compound represented by Formula 1 is the hole injection layer and the hole transport layer. An organic light-emitting device that is included in at least one of a layer for simultaneously injecting and transporting holes and a hole controlling layer. The method of claim 8, wherein the organic material layer includes at least one of an electron injection layer, an electron transport layer, a layer for simultaneously injecting and transporting electrons, and an electron controlling layer, and the compound represented by Formula 1 is the electron injection layer and the electron transport layer. , An organic light-emitting device that is included in at least one of a layer and an electron control layer for simultaneously injecting and transporting electrons.

Images