CN111051323B

CN111051323B - Compound and organic light emitting device including the same

Info

Publication number: CN111051323B
Application number: CN201980003956.8A
Authority: CN
Inventors: 金曙渊; 朴钟镐; 徐尚德; 李东勋; 朴胎润
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2018-05-14
Filing date: 2019-05-14
Publication date: 2022-12-16
Anticipated expiration: 2039-05-14
Also published as: WO2019221445A1; KR102206814B1; KR20190130409A; CN111051323A

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 including the same

Technical Field

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

The present application claims priority to korean patent application No. 10-2018-0055073, which was filed on 14.05.2018 to the korean patent office, the entire contents of which are incorporated in the present specification.

Background

Generally, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode with an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light emitting device, the organic layer is formed of a multi-layer structure composed of different materials, 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. With the structure of such an organic light emitting device, if a voltage is applied between both electrodes, holes are injected from the anode to the organic layer, electrons are injected from the cathode to the organic layer, an exciton (exiton) is formed when the injected holes and electrons meet, and light is emitted when the exciton falls back to the ground state.

There is a continuing demand for the development of new materials for organic light emitting devices as described above.

Documents of the prior art

Korean laid-open patent publication No. 10-2004-0049038

Disclosure of Invention

Technical subject

The present specification provides an organic light emitting device having a low driving voltage, a high light emitting efficiency, an excellent life characteristic, or a high color purity by including the compound represented by chemical formula 1 in the organic light emitting device.

Means for solving the problems

One embodiment of the present specification provides a compound represented by the following chemical formula 1.

[ chemical formula 1]

In the above-described chemical formula 1,

adjacent 2 of Y1 to Y4 are carbon atoms to which two "+" of the following chemical formula D are bonded respectively, one of two of Y1 to Y4 which are not bonded is N, and the other is N or CR1,

[ chemical formula D ]

In the chemical formula D described above,

x is O, S, se, S (= O), NRm, siRmRn or CRmRn,

r1 to R3, rm, rn, rx, ry and Rz, equal to or different from each other, are each independently hydrogen, deuterium, alkyl, alkenyl, alkynyl, halogen group, hydroxyl group, alkoxy group, aryloxy group, silyl group substituted or unsubstituted with alkyl or aryl group, aryl group or heteroaryl group, or combine with each other with adjacent groups to form a ring substituted or unsubstituted with one or more substituents selected from deuterium, alkyl group, alkenyl group, alkynyl group, halogen group, hydroxyl group, alkoxy group, aryloxy group, silyl group substituted or unsubstituted with alkyl or aryl group, aryl group and heteroaryl group,

a is an integer of 0 to 4, and when a is 2 or more, plural R3 s are the same or different from each other.

An embodiment of the present specification provides an organic light emitting device including: the organic light emitting device includes a first electrode, a second electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein the compound represented by the chemical formula 1 is included in one or more of the one or more organic layers.

Effects of the invention

In one embodiment of the present invention, when the compound represented by the above chemical formula 1 is included in an organic layer, particularly, a light emitting layer of an organic light emitting device, it is possible to achieve an improvement in efficiency of the device, a reduction in driving voltage of the device, or an improvement in lifetime characteristics of the device.

Drawings

Fig. 1 illustrates an example of an organic light emitting device composed of a substrate 1, an anode 2, an organic layer 3, and a cathode 4.

Fig. 2 illustrates an example of an organic light emitting device composed of 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, an electron injection and transport layer 10, and a cathode 4.

< description of symbols >

1: substrate

2: anode

3: organic layer

4: cathode electrode

5: hole injection layer

6: a first hole transport layer

7: second hole transport layer

8: luminescent layer

9: electron transport layer

10: electron injection and transport layer

Detailed Description

The present invention will be described in more detail below.

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

In the context of the present specification,

indicates a site to which another substituent or a binding moiety binds.

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 a hydrogen atom can be substituted, that is, a position at which the substituent can be substituted. When the number of the substituents is 2 or more, 2 or more substituents may be the same or different from each other.

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

Specific examples of the chain alkyl group include, but are not limited to, 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-dimethylbutyl, 2-ethylbutyl, heptyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethylpropyl, 1-dimethylpropyl, isohexyl, 4-methylhexyl, and 5-methylhexyl.

The number of carbon atoms of the cyclic alkyl (cycloalkyl) group is not particularly limited, but is preferably 3 to 20. According to one embodiment, the cycloalkyl group has 3 to 16 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 12. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 8. Specific 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, and cyclooctyl.

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 one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. Specific examples of the alkenyl group include an ethenyl group (A)

Ethenyl) is vinyl group (a)

vinyl), propenyl, allyl, isopropenyl, butenyl, isobutenyl, n-pentenyl and n-hexenyl, but is 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 embodiment, the number of carbon atoms of the alkynyl group is 2 to 20. Specific examples of the alkynyl group include, but are not limited to, a alkynyl group, an ethynyl group, a 2-propynyl group, a 2-butynyl group, a 1-methyl-2-butynyl group, and a 2-pentynyl group.

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

In the present specification, the alkoxy group means 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 one embodiment, the alkoxy group has 1 to 20 carbon atoms. According to another 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, isobutoxy, sec-butoxy, pentyloxy, isopentyloxy, hexyloxy, and the like. The alkyl group of the above alkoxy group can be applied to the above description of the alkyl group.

In the present specification, an aryloxy group means a group having an aryl group bonded to an oxygen atom. Specific examples of the aryloxy group include, but are not limited to, phenoxy, 1-naphthoxy, 3-methylphenoxy, and 4-methoxyphenoxy. As the aryl group of the above aryloxy group, the aryl group described later can be applied.

In this specification, the silyl group may be represented by-SiR ₁₁ R ₁₂ R ₁₃ The above chemical formula (II) represents ₁₁ To R ₁₃ Each independently may be hydrogen, alkyl or aryl. In the present specification, alkylsilyl group means a silyl group substituted with an alkyl group, and arylsilyl group means a silyl group substituted with an aryl group. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

In the present specification, aryl means a substituted or unsubstituted monocyclic or polycyclic ring which is wholly or partially unsaturated. According to one embodiment, the aryl group has 6 to 30 carbon atoms. The above aryl group may be a monocyclic aryl group or a polycyclic aryl group. Examples of the monocyclic aryl group include, but are not limited to, phenyl, biphenyl, terphenyl, and the like. Examples of the polycyclic aromatic group include naphthyl, anthryl, phenanthryl, perylenyl, fluoranthenyl, triphenylenyl, phenalenyl, pyrenyl, tetracenyl, perylene, and the like,

And a group such as a phenyl group, a fluorenyl group, an indenyl group, an acenaphthenyl group, a benzofluorenyl group, a spirofluorenyl group, etc., but is 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.

As the above-mentioned substituted fluorenyl group, there are

And the like, but is not limited thereto.

In the present specification, a heteroaryl group is a cyclic group containing one or more of N, O and S as a heteroatom, 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 of the heteroaryl group is from 2 to 30. According to another embodiment, the above heteroaryl has 2 to 20 carbon atoms. Examples of heteroaryl groups include thienyl, furyl, imidazolyl, thiazolyl, and the like,

Azolyl group,

Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, acenaphthoquinoxalinyl, indenoquinazolinyl, indenoisoquinolinyl, indenoquinolinyl, pyridoindolyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolyl, indolyl, benzo [ b ] pyrazinyl, indolyl, benzo [ b ] indolyl, and a pharmaceutically acceptable salt thereof

Azolyl, benzimidazolyl, benzothiazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazolyl, and isoazolyl

Azole group,

Diazolyl, thiaOxadiazolyl, benzothiazolyl, thiophen

Oxazinyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.

In the present specification, an "adjacent" group may refer to a substituent substituted on an atom directly connected to an atom substituted with the substituent, a substituent closest in steric structure to the substituent, or another substituent substituted on an atom substituted with the substituent. For example, 2 substituents substituted in the ortho (ortho) position in the phenyl ring and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the term "form a ring by bonding adjacent groups to each other" means that a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a fused ring thereof is formed by bonding adjacent groups to each other. The hydrocarbon ring is a ring composed of only carbon atoms and hydrogen atoms, and the hydrocarbon ring may be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocyclic ring refers to a ring containing one or more heteroatoms, and the heterocyclic ring may be an aliphatic heterocyclic ring or an aromatic heterocyclic ring. In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring and the aromatic heterocyclic ring may be monocyclic or polycyclic.

The aliphatic hydrocarbon ring is not an aromatic ring and is a ring composed of only carbon atoms 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, but are not limited thereto.

The aromatic hydrocarbon ring refers to an aromatic ring composed of only carbon atoms and hydrogen atoms. As an example of the aromatic hydrocarbon ring, with benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene,

Pentacene, fluorene, indene, acenaphthylene, phenylfluorene, spirofluorene, etc., but are not limited thereto.

The aliphatic heterocyclic ring refers to an aliphatic ring containing 1 or more heteroatoms. As examples of the aliphatic heterocyclic ring, ethylene oxide (oxirane), tetrahydrofuran, 1, 4-bis (t-butyl ether) and the like are given

Alkanes (1, 4-dioxane), pyrrolidine, piperidine, morpholine (morpholinone), oxepane (oxepane)

) Azacyclooctane

Thiocyclooctane

And the like, but is not limited thereto.

The aromatic heterocyclic ring refers to an aromatic ring containing 1 or more heteroatoms. Examples of the aromatic heterocyclic ring include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, and the like,

Oxazole and iso

Oxazole, thiazole, isothiazole, triazole, and the like,

Diazoles, thiadiazoles, dithiazoles, tetrazoles, pyrans, thiopyrans, diazines,

Oxazine, thiazine, II

Alkene, triazine, tetrazine, isoquinoline, quinoline, quinazolineQuinoxaline, naphthyridine, acridine, phenanthridine, naphthyridine, triazabine, indole, indolizine, benzothiazole, benzpyrole

Oxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, thiophene

Oxazines, phenanthridines, indolocarbazoles, indenocarbazoles, and the like, but are not limited thereto.

One embodiment of the present specification provides a compound represented by the above chemical formula 1.

In the above chemical formula 1, adjacent two of the above Y1 to Y4 mean Y1 and Y2, Y2 and Y3, or Y3 and Y4.

In one embodiment of the present specification, R1 is hydrogen, deuterium, or an alkyl group.

In one embodiment of the present specification, R1 is hydrogen or methyl.

In one embodiment of the present specification, R1 is hydrogen.

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

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

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

In one embodiment of the present specification, R2 is hydrogen, methyl or isopropyl.

In one embodiment of the present specification, R3 is hydrogen, deuterium, or an alkyl group, or is bonded to an adjacent group to form a ring which is unsubstituted or substituted with one or more substituents selected from deuterium and an alkyl group.

In one embodiment of the present specification, R3 is hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms, or is bonded to an adjacent group to form a benzene ring which is unsubstituted or substituted with one or more substituents selected from deuterium and an alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, R3 is hydrogen, deuterium, or an alkyl group having 1 to 6 carbon atoms, or is bonded to an adjacent group to form a benzene ring which is unsubstituted or substituted with one or more substituents selected from deuterium and an alkyl group having 1 to 6 carbon atoms.

In one embodiment of the present specification, R3 is hydrogen, deuterium, methyl, or tert-butyl, or is bonded to an adjacent group to form a benzene ring.

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

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

In one embodiment of the present specification, rm and Rn are the same or different and each independently hydrogen, deuterium, or an alkyl group.

In one embodiment of the present specification, rm and Rn are the same or different and each independently hydrogen, deuterium, or an alkyl group having 1 to 6 carbon atoms.

In one embodiment of the present specification, rm and Rn are the same or different and each independently hydrogen, deuterium, or an alkyl group having 1 to 3 carbon atoms.

In one embodiment of the present specification, rm and Rn are the same or different and each independently hydrogen or methyl.

In one embodiment of the present specification, rx and Rz are the same or different from each other and each independently represents a linear or branched chain alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms.

In one embodiment of the present specification, rx and Rz are the same or different from each other and each independently represents a linear or branched chain alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms.

In one embodiment of the present specification, rx and Rz are the same or different from each other and each independently represents a linear or branched chain alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms.

In one embodiment of the present specification, rx and Rz are the same as or different from each other and each independently represents a methyl group, an isopropyl group, a 1-ethylpropyl group, a tert-butyl group or a cyclohexyl group.

In one embodiment of the present specification, ry is hydrogen.

In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulae 1-1 to 1-4.

[ chemical formula 1-1]

[ chemical formulas 1-2]

[ chemical formulas 1-3]

[ chemical formulas 1-4]

In the above chemical formula 1-1,

adjacent 2 of Y2 to Y4 are carbon atoms bonded to two "+" of said chemical formula D, respectively, one of Y2 to Y4 not bonded to the "+" of said chemical formula D is N or CR1,

in the above chemical formula 1-2,

y3 and Y4 are each a carbon atom bonded to each of two "+" of the above chemical formula D, Y1 is N or CR1,

in the above-mentioned chemical formulas 1 to 3,

y1 and Y2 are each a carbon atom bonded to each of two "-" groups of the above formula D, Y4 is N or CR1,

in the above-mentioned chemical formulas 1 to 4,

adjacent 2 of Y1 to Y3 are carbon atoms bonded to two "+" of the above chemical formula D, respectively, one of Y1 to Y3 not bonded to the "+" of the above chemical formula D is N or CR1,

r1, R3, rx, ry, rz and a are as defined in chemical formula 1.

In one embodiment of the chemical formula 1-1, one of Y2 to Y4 not bonded to "+" of the chemical formula D is CR1.

In one embodiment of the above chemical formula 1-2, Y1 is CR1.

In one embodiment of the above chemical formulas 1 to 3, Y4 is CR1.

In one embodiment of the above chemical formulas 1 to 4, one of the Y1 to Y3 that is not bonded to "+" of the above chemical formula D is CR1.

In one embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 2-1 or chemical formula 2-2.

[ chemical formula 2-1]

[ chemical formula 2-2]

In the above chemical formula 2-1 and chemical formula 2-2,

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

x, R1 to R3, rx, ry, rz and a are the same as defined in chemical formula 1.

In one embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 3-1 or 3-2.

[ chemical formula 3-1]

[ chemical formula 3-2]

In the above chemical formula 3-1 and chemical formula 3-2,

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

x, R1 to R3, rx, ry, rz and a are as defined in chemical formula 1.

In one embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 4-1 or chemical formula 4-2.

[ chemical formula 4-1]

[ chemical formula 4-2]

In the above chemical formulas 4-1 and 4-2,

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

x, R1 to R3, rx, ry, rz and a are the same as defined in chemical formula 1.

In one embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 5.

[ chemical formula 5]

In the above-mentioned chemical formula 5,

y1 to Y4, rx, ry and Rz are as defined in chemical formula 1,

r4 is hydrogen, deuterium, alkyl, alkenyl, alkynyl, halogen group, hydroxyl, alkoxy, aryloxy, silyl substituted or unsubstituted with alkyl or aryl, or heteroaryl,

b is an integer of 0 to 6, and when b is 2 or more, R4 s may be the same or different from each other.

In one embodiment of the present specification, R4 is hydrogen, deuterium, or an alkyl group.

In one embodiment of the present specification, R4 is hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, R4 is hydrogen, deuterium, or an alkyl group having 1 to 6 carbon atoms.

In one embodiment of the present specification, R4 is hydrogen, deuterium, methyl, or tert-butyl.

In one embodiment of the present specification, (1) R3 is an alkyl group and a is 2, or (2) chemical formula 1 is represented by chemical formula 5.

In one embodiment of the present specification, the above

Is a group represented by the following chemical formula 6-1 or 6-2.

[ chemical formula 6-1]

[ chemical formula 6-2]

In the above chemical formulas 6-1 and 6-2,

r31 to R7 are the same as or different from each other, and each independently hydrogen, deuterium, an alkyl group, an alkenyl group, an alkynyl group, a halogen group, a hydroxyl group, an alkoxy group, an aryloxy group, a silyl group substituted with an alkyl group or an aryl group or unsubstituted, an aryl group, or a heteroaryl group,

c is an integer of 0 to 4, and when c is 2 or more, R37's are the same or different from each other.

In one embodiment of the present specification, at least 2 of R31 to R34 are alkyl groups.

In one embodiment of the present specification, R31 and R33 are hydrogen.

In one embodiment of the present specification, R32 and R34 are the same as or different from each other and each independently represents an alkyl group.

In one embodiment of the present specification, R32 and R34 are the same or different and each independently an alkyl group having 1 to 6 carbon atoms.

In one embodiment of the present specification, R32 and R34 are the same or different and each independently a methyl group.

In one embodiment of the present specification, R35 is hydrogen.

In one embodiment of the present specification, R37 is hydrogen.

In one embodiment of the present specification, R36 is hydrogen or an alkyl group.

In one embodiment of the present specification, R36 is hydrogen or an alkyl group having 1 to 6 carbon atoms.

In one embodiment of the present specification, R36 is hydrogen or tert-butyl.

In one embodiment of the present specification, the compound represented by the above chemical formula 1 is any one selected from the following compounds.

In one embodiment of the present specification, the compound represented by the above chemical formula 2-1 can be produced by the method of the following general formula 1.

[ general formula 1]

The above formula 1 is an example of a method of forming the compound represented by chemical formula 2-1, and the method of synthesizing the compound represented by chemical formula 2-1 is not limited to the above formula 1, and a part of the synthesis steps may be based on a method known in the art.

In the above general formula 1, when main ligands having different kinds of the condensed positions and substituents of the five-membered ring are used, other compounds represented by chemical formula 1 can be produced.

The present specification provides an organic light emitting device comprising the compound represented by the above chemical formula 1.

An embodiment of the present specification provides an organic light emitting device including: the organic light emitting device includes a first electrode, a second electrode, and one or more organic layers between the first electrode and the second electrode, wherein the compound represented by the chemical formula 1 is contained in one or more of the one or more organic layers.

The organic light emitting device of the present specification may include a single layer or a plurality of layers of organic layers between the first electrode and the second electrode. For example, the organic layer included in the organic light emitting device of the present invention may be one or more layers of a hole injection layer, a hole transport layer, a layer simultaneously performing hole injection and transport, a hole adjusting layer, a light emitting layer, an electron adjusting layer, an electron transport layer, an electron injection layer, and a layer simultaneously performing electron transport and injection.

In one embodiment of the present specification, the compound represented by the above chemical formula 1 is contained in 1 or more layers among 1 or more light-emitting layers.

In one embodiment of the present specification, the light-emitting layer including the compound represented by the above chemical formula 1 is a red light-emitting layer.

In one embodiment of the present specification, when the organic light emitting device includes 1 or more light emitting layers, the light emitting layers may display different colors from each other.

In one embodiment of the present specification, the organic light emitting device including the compound represented by the above chemical formula 1 is a red organic light emitting device.

In one embodiment of the present specification, the compound represented by the above chemical formula 1 is contained 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 containing the compound.

In one embodiment of the present specification, the light-emitting layer including the compound represented by chemical formula 1 further includes a host material.

In one embodiment of the present specification, the host substance included in the light-emitting layer including the compound represented by the above chemical formula 1 is a carbazole derivative compound or an N-containing aromatic polycyclic compound.

In one embodiment of the present specification, the light-emitting layer including the compound represented by chemical formula 1 further includes a host compound represented by chemical formula H.

[ chemical formula H ]

In the above-mentioned chemical formula H,

g1 and G2, which may be the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, an alkyl group, a cycloalkyl group, a silyl group, an aryl group, or a heteroaryl group, or combine with each other to form a ring,

g3 and G4, equal to or different from each other, are each independently an aryl group substituted or unsubstituted with an alkyl, aryl or heteroaryl group; or heteroaryl, unsubstituted or substituted by alkyl, aryl or heteroaryl,

b1 is an integer of 0 to 7, and when b1 is 2 or more, G1 s may be the same or different from each other,

b2 is an integer of 0 to 7, and when b2 is 2 or more, G2 s may be the same or different from each other.

In one embodiment of the present specification, G1 and an adjacent group are bonded to each other to form a benzene ring.

In one 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 which contains N.

In one embodiment of the present specification, G4 is a heteroaryl group which is unsubstituted or substituted by an alkyl group, an aryl group or a heteroaryl group, and which includes a six-membered ring containing N.

In one embodiment of the present specification, the chemical formula H is represented by the following chemical formula H-1.

[ chemical formula H-1]

In the above-mentioned chemical formula H-1,

g1 to G4 and b2 are as defined in formula H,

b3 is an integer of 0 to 9, and when b3 is 2 or more, G1 s may be the same or different from each other.

In one embodiment of the present specification, the compound represented by the above chemical formula H is the following compound.

In one embodiment of the present specification, the compound represented by the above chemical formula 1 is contained in 1 or more layers of the hole injection layer, the hole transport layer, the layer in which hole injection and transport are simultaneously performed, and the hole adjusting layer.

In one embodiment of the present specification, the compound represented by the above chemical formula 1 is contained in 1 or more layers of an electron injection layer, an electron transport layer, a layer in which electron injection and transport are simultaneously performed, and an electron adjustment layer.

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

In one embodiment of the present specification, the organic light emitting device may have a reverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

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

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

A structure of an organic light emitting device according to an embodiment of the present specification is illustrated in fig. 1 and 2.

An organic light emitting device according to an embodiment of the present invention may be composed of a substrate 1, an anode 2, an organic layer 3, and a cathode 4, as shown in fig. 1. In one embodiment, the compound represented by the chemical formula 1 is contained in the organic layer 3.

An organic light emitting device according to an embodiment of the present invention may be composed of 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, an electron injection and transport layer 10, and a cathode 4, as shown in fig. 2. In one embodiment, the compound represented by the chemical formula 1 is included in the light emitting layer 8.

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

(1) Anode/hole transport layer/light emitting layer/cathode

(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode

(3) Anode/hole transport layer/light emitting layer/electron transport layer/cathode

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

(8) Anode/hole transport layer/hole-adjusting layer/light-emitting layer/electron transport layer/electron-injecting layer/cathode

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

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

(11) Anode/hole transport layer/luminescent layer/electron modulating layer/electron transport layer/cathode

(12) Anode/hole transport layer/luminescent layer/electron modulating layer/electron transport layer/electron injection layer/cathode

(13) Anode/hole injection layer/hole transport layer/luminescent layer/electron regulation layer/electron transport layer/cathode

(14) Anode/hole injection layer/hole transport layer/luminescent layer/electron regulation layer/electron transport layer/electron injection layer/cathode

When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating a first electrode, an organic layer, and a second electrode on a substrate. This can be produced as follows: the organic el device is manufactured by depositing a metal, a conductive metal oxide, or an alloy thereof on a substrate by a Physical Vapor Deposition (PVD) method such as a sputtering method or an electron beam evaporation (e-beam evaporation) method to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer.

In addition, the compound represented by the above chemical formula 1 may be formed into an organic layer not only by a vacuum evaporation method but also by a solution coating method in the manufacture of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

In addition to these methods, an organic light-emitting device can be manufactured by depositing a cathode material, an organic material layer, and an anode material on a substrate in this order (international patent application publication No. 2003/012890). However, the production method is not limited thereto.

The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); such as ZnO: al or SnO ₂ : a combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.

The cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; such as LiF/Al or LiO ₂ And a multilayer structure material such as Al, but not limited thereto.

The hole injection layer is a layer that injects holes received from the electrode into the light-emitting layer or an adjacent layer provided on the light-emitting layer side. As the hole injecting substance, the following compounds are preferably used: has an ability to transport holes, has a hole injection effect from the anode, has an excellent hole injection effect for the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material, and has excellent thin film-forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole-transporting substance is a substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer, and is preferably a substance having a high mobility to holes. Specific examples of the hole transporting substance include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.

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

The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As a specific example, there are8-hydroxyquinoline aluminum complex (Alq) ₃ ) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo [ b ]

Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material.

The host material may be an aromatic fused ring derivative, a heterocyclic ring-containing compound, or the like. Specifically, the aromatic fused ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include dibenzofuran derivatives and ladder furan compounds

Pyrimidine derivatives, etc., but are not limited thereto.

As the dopant material of the light-emitting layer, there are an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. The aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamine group, and pyrene, anthracene, or the like having an arylamine group can be used,

Diindenopyrene, and the like. The styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine. Examples of the styrene amine include, but are not limited to, styrene amine, styrene diamine, styrene triamine, and styrene tetramine. As the metal complex, an iridium complex, a platinum complex, or the like can be used, but the metal complex is not limited thereto.

The electron control layer is a layer that blocks holes from flowing from the light-emitting layer to the cathode and controls electrons flowing into the light-emitting layer, thereby controlling the performance of the entire device. The electron-regulating substance is preferably a compound having the ability to prevent holes from flowing from the light-emitting layer to the cathode and to regulate electrons injected into the light-emitting layer or the light-emitting material. As the electron-adjusting substance, an appropriate substance can be used depending on the composition of the organic layer used in the device. The electron control layer is preferably provided between the light-emitting layer and the cathode, and is preferably directly connected to the light-emitting layer.

The electron transport layer receives electrons from the electron injection layer and transports the electrons to the light emitting layer. The electron-transporting substance is a substance that can inject electrons from the cathode and transfer the electrons to the light-emitting layer, and is preferably a substance having a high electron mobility. As examples of the above electron transporting substance, there are Al complexes of 8-hydroxyquinoline, al complexes containing Alq ₃ The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer described above may be used with any desired cathode material as used in the prior art. In one embodiment, as the cathode material, a material having a low work function, and an aluminum layer or a silver layer can be used. Examples of the substance having a low work function include cesium, barium, calcium, ytterbium, samarium, and the like, and after a layer is formed from the substance, an aluminum layer or a silver layer may be formed on the layer.

The electron injection layer is a layer that injects electrons received from the electrode into the light-emitting layer. As the electron-injecting substance, the following compounds are preferably used: the organic light-emitting device has an ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole-injecting layer or a hole-injecting material, and has excellent thin-film formability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,

Azole,

Oxadiazole, triazole, imidazole, benzimidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex include, but are not limited to, lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), gallium tris (8-quinolinolato), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium bis (2-methyl-8-quinolinolato) chloride, gallium bis (2-methyl-8-quinolinolato) (o) gallium, bis (2-methyl-8-quinolinolato) (1-naphthol) aluminum, and gallium bis (2-methyl-8-quinolinolato) (2-naphthol) gallium.

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

Modes for carrying out the invention

Hereinafter, in order to help the detailed understanding of the present invention, the method for manufacturing the compound of the present invention and the organic light emitting device including the same, and the characteristics thereof will be described.

[ production example ]

Production example 1: synthesis of Compound 1

(1) Production of intermediate A1

In a round-bottom flask, under nitrogen atmosphere, add 7-chloro-2-methyl

Azolo [4,5-d]Pyrimidine (7-chloro-2-methoxyxazolo [4, 5-d)]pyrimidine) (50g, 0.3 mol) and (3, 5-dimethylphenyl) boronic acid (49g, 0.32mol) were dissolved in 500ml of THF, and 2M aqueous potassium carbonate (200 ml) was added, and tetrakis (triphenylphosphine) palladium (10g, 9mmol) was added, followed by stirring with heating at 70 ℃ for 5 hoursWhen the user wants to use the device. After the reaction was completed, the temperature was lowered, and after separating the aqueous layer, the solvent in the organic layer was removed. After dissolving with chloroform (chloroform), the mixture was washed with water, added with magnesium sulfate (magnesium sulfate) and an acidic clay, stirred, filtered, and concentrated under reduced pressure. Column chromatography was then performed with hexane (hexane) and ethyl acetate (20: 1 by volume) to produce intermediate A1 (54 g, 82% yield).

(2) Production of intermediate A2

Iridium chloride (iridium chloride) (30g, 0.1mol) and intermediate A1 (54g, 0.26mol) were added to 1500ml of 2-ethoxyethanol (2-ethoxyyenanol) and 500ml of distilled water in a round-bottom flask under nitrogen atmosphere, and stirred with heating at 130 ℃ for 24 hours. After the temperature was lowered to room temperature and filtration, the filtrate was washed with 2L of ethanol, thereby producing a solid compound A2 (34.3 g, yield 53%).

(3) Production of Compound 1

Intermediate A2 (34.3g, 0.03mol), acetylacetone (acetylacetatone) (7.5g, 0.75mol), and potassium carbonate (potassiumcbonate) (10g, 0.75mol) were dissolved in 400ml of 2-ethoxyethanol under a nitrogen atmosphere, and then heated and stirred at 50 ℃ for 28 hours. After the reaction, the temperature was reduced to normal temperature, and the reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. Then, the product was purified by column chromatography using Dichloromethane (dichromethane) and methanol (methanol) (50 by volume. (18 g, yield 43%, MS: [ M + H ]] ⁺ ＝712.8)

Production example 2: synthesis of Compound 2

The above-mentioned compound 2 was produced by the same method as the method for producing the compound 1 except that 2, 6-tetramethylheptane-3,5-dione (2, 6-tetramethylheptane-3, 5-dione) was used in place of acetylacetone (acetylacetazone). (yield 52%, MS: [ M + H ]] ⁺ ＝796.9)

Production example 3: synthesis of Compound 3

The above compound 3 was produced by the same method as the production method of the compound 1 except that 3,7-diethylnonane-4,6-dione (3, 7-dimethylnonane-4, 6-dione) was used instead of acetylacetone (acetylacetatone). (yield 50%, MS: [ M + H ]] ⁺ ＝825)

Production example 4: synthesis of Compound 4

(1) Production of intermediate A3

Use of 7-chloro-2-methyl in a flask

Azolo [5,4-d]Pyrimidine (7-chloro-2-methyloxazolo [5,4-d ]]pyrimidine) (45g, 0.26mol) in place of 7-chloro-2-methyl

Azolo [4,5-d ] s]Pyrimidine (7-chloro-2-methyloxazolo [4,5-d ]]pyrimidine), the above intermediate A3 was produced by the same method as that for producing the compound 1, except that pyrimidine). (56 g, yield 90%)

(2) Production of intermediate A4

The intermediate A4 was produced by the same method as the method for producing the intermediate A2, except that the intermediate A3 was used instead of the intermediate A1. (31 g, yield 48%)

(3) Production of Compound 4

The above compound 4 was produced by the same method as the method for producing the compound 1, except that the intermediate A4 was used instead of the intermediate A2. (17 g, yield 43%, MS: [ M + H ]] ⁺ ＝712.8)

Production example 5: synthesis of Compound 5

The above compound 5 was produced by the same method as the method for producing the compound 1 except that the intermediate A4 was used instead of the intermediate A2 and 2, 6-tetramethylheptane-3,5-dione was used instead of acetylacetone. (11 g, yield 57%, MS: [ M + H ]] ⁺ ＝796.9)

Production example 6: synthesis of Compound 6

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

Production example 7: synthesis of Compound 7

(1) Production of intermediate A5

In a round-bottomed flask, 3,4-dibromo-6-chloropyridazine (3, 4-dibromo-6-chloropyridazine) (30g, 0.26mol) and acetamide (13g, 0.29mol) and triethylamine (triethylhydroxylamine) (52g, 0.52mol) were dissolved in 500ml of tetrahydrofuran (tetrahydrofuran) under a nitrogen atmosphere, and then stirred at ordinary temperature for 8 hours. After the reaction is finished, 1M chloride aqueous solution is poured into the reactor

100ml of the mixture was quenched, and the organic layer was separated by pouring an aqueous ammonium chloride solution (ammonium chloride solution) and then distilled under reduced pressure. Dissolving in 300ml chloroform, adding acidic clay and MgSO ₄ After stirring, it was filtered through celite. The filtrate was distilled under reduced pressure, and then purified by column chromatography using hexane and ethyl acetate (25Intermediate A5. (23 g, yield 65%)

(2) Production of intermediate A6

Use of intermediate A5 instead of 7-chloro-2-methyl

Azolo [4,5-d]Pyrimidine (7-chloro-2-methyloxazolo [4,5-d ]]pyrimidine), the above intermediate A6 was produced by the same method as that for the production of the intermediate A1, except that pyrimidine). (28 g, yield 73%)

(3) Production of intermediate A7

The intermediate A7 was produced by the same method as the method for producing the intermediate A2, except that the intermediate A6 was used instead of the intermediate A1. (31 g, yield 48%)

(4) Production of Compound 7

The above compound 7 was produced by the same method as the method for producing the compound 1, except that the intermediate A7 was used instead of the intermediate A2. (15 g, yield 41%, MS: [ M + H ]] ⁺ ＝712.8)

Production example 8: synthesis of Compound 8

The above compound 8 was produced by the same method as the method for producing the compound 1, except that the intermediate A7 was used in place of the intermediate A2 and 2, 6-tetramethylheptane-3,5-dione was used in place of acetylacetone. (19 g, yield 58%, MS: [ M + H ]] ⁺ ＝796.9)

Production example 9: synthesis of Compound 9

The above compound 9 was produced by the same method as the production method of the compound 1 except that the intermediate A7 was used instead of the intermediate A2 and 3,7-diethylnonane-4,6-dione was used instead of acetylacetone. (10 g, yield 48%, MS: [ M + H ]] ⁺ ＝825)

Production example 10: synthesis of Compound 10

(1) Production of intermediate A8

The intermediate A8 was produced by the same method as the method for producing the intermediate A5, except that ethanethioamide was used instead of acetylacetone. (37 g, yield 61%)

(2) Production of intermediate A9

Use of intermediate A8 instead of 7-chloro-2-methyl

Azolo [4,5-d ] s]Pyrimidine (7-chloro-2-methyloxazolo [4,5-d ]]pyrimidine), the above intermediate A9 was produced by the same method as the method for producing the intermediate A1, except that. (51 g, yield 83%)

(3) Production of intermediate A10

The intermediate a10 was produced by the same method as the method for producing the intermediate A2, except that the intermediate A9 was used instead of the intermediate A1. (45 g, yield 50%)

(4) Production of Compound 10

The above compound 10 was produced by the same method as the method for producing the compound 1, except that the intermediate a10 was used instead of the intermediate A2. (37 g, yield 45%, MS: [ M + H ]] ⁺ ＝744.9)

Production example 11: synthesis of Compound 11

The above compound 11 was produced by the same method as the method for producing the compound 1, except that the intermediate a10 was used in place of the intermediate A2 and 2, 6-tetramethylheptane-3,5-dione was used in place of acetylacetone. (23 g, yield 47%, MS: [ M + H ]] ⁺ ＝829)

Production example 12: synthesis of Compound 12

The above compound 12 was produced by the same method as the production method of the compound 1 except that the intermediate a10 was used instead of the intermediate A2 and 3,7-diethylnonane-4,6-dione was used instead of acetylacetone. (28 g, yield 52%, MS: [ M + H ]] ⁺ ＝857.1)

Production example 13: synthesis of Compound 13

(1) Production of intermediate A11

The above intermediate a11 was produced by the same method as the method for producing the intermediate A5, except that 2,3-dibromo-5-chloropyrazine (2, 3-dibromo-5-chloropyrazine) was used instead of 3, 4-dibromo-6-chloropyridazine. (40 g, yield 63%)

(2) Production of intermediate A12

Use of intermediate A11 instead of 7-chloro-2-methyl

Azolo [4,5-d ] s]Pyrimidine (7-chloro-2-methoxyxazolo [4, 5-d)]pyrimidine), the above intermediate a12 was produced by the same method as that for the production of the intermediate A1, except that pyrimidine). (56 g, yield 73%)

(3) Production of intermediate A13

The above intermediate a13 was produced by the same method as the method for producing the intermediate A2, except that the intermediate a12 was used instead of the intermediate A1. (33 g, yield 46%)

(4) Production of Compound 13

The above compound 13 was produced by the same method as the method for producing the compound 1, except that the intermediate a13 was used instead of the intermediate A2. (25 g, yield 41%, MS: [ M + H ]] ⁺ ＝712.8)

Production example 14: synthesis of Compound 14

The above compound 14 was produced by the same method as the method for producing the compound 1, except that the intermediate a13 was used in place of the intermediate A2 and 2, 6-tetramethylheptane-3,5-dione was used in place of acetylacetone. (14 g, yield 43%, MS: [ M + H ]] ⁺ ＝796.9)

Production example 15: synthesis of Compound 15

The above compound 15 was produced by the same method as the production method of the compound 1 except that the intermediate a13 was used in place of the intermediate A2 and 3,7-diethylnonane-4,6-dione was used in place of acetylacetone. (13 g, yield 45%, MS: [ M + H ]] ⁺ ＝825)

Production example 16: synthesis of Compound 16

(1) Production of intermediate A16

Use of intermediate A5 instead of 7-chloro-2-methyl

Azolo [4,5-d]Pyrimidine (7-chloro-2-methyloxazolo [4,5-d ]]pyrimidine), the above intermediate a16 was produced by the same method as the method for producing the intermediate A1, except that 2-naphthoic acid (naphthalene-2-ylboronic acid) was used instead of (3, 5-dimethylphenyl) boronic acid. (36 g, yield 88%)

(3) Production of intermediate A17

The intermediate a17 was produced by the same method as the method for producing the intermediate A2, except that the intermediate a16 was used instead of the intermediate A1. (18 g, yield 47%)

(4) Production of Compound 16

The above compound 16 was produced by the same method as the method for producing the compound 1, except that the intermediate a17 was used in place of the intermediate A2 and 2, 6-tetramethylheptane-3,5-dione was used in place of acetylacetone. (11 g, yield 42%, MS: [ M + H ]] ⁺ ＝897)

Production example 17: synthesis of Compound 17

(1) Production of intermediate A18

Use of intermediate A5 instead of 7-chloro-2-methyl

Azolo [4,5-d]Pyrimidine (7-chloro-2-methyloxazolo [4,5-d ]]pyrimidine) and the intermediate a18 was produced by the same method as that for the production of the intermediate A1, except that (4- (tert-butyl) naphthalene-2-yl) boronic acid was used instead of (3, 5-dimethylphenyl) boronic acid (4- (tert-butyl) naphthalene-2-yl) boronic acid. (42 g, yield 77%)

(3) Production of intermediate A19

The above intermediate a19 was produced by the same method as the method for producing the intermediate A2, except that the intermediate a18 was used instead of the intermediate A1. (22 g, yield 51%)

(4) Production of Compound 17

The above compound 17 was produced by the same method as the method for producing the compound 1, except that the intermediate a19 was used instead of the intermediate A2 and 2, 6-tetramethylheptane-3,5-dione was used instead of acetylacetone. (15 g, yield 46%, MS: [ M + H ]] ⁺ ＝1009.3)

Production example 18: synthesis of Compound 18

(1) Production of intermediate A20

Using 7-chloro-2-methylthiazolo [4,5-d ]]Pyrimidine (7-chloro-2-methlthiazolo [4, 5-d)]pyrimidine) (30g, 0.1umol) instead of 7-chloro-2-methyl

Azolo [4,5-d ] s]The above intermediate a20 was produced by the same method as the method for producing the intermediate A1, except that pyrimidine was used in place of (3, 5-dimethylphenyl) boronic acid (4- (tert-butyl) naphthalen-2-yl) boronic acid. (39 g, yield 72%)

(3) Production of intermediate A21

The intermediate a21 was produced by the same method as the method for producing the intermediate A2, except that the intermediate a20 was used instead of the intermediate A1. (24 g, yield 50%)

(4) Preparation of Compound 18

The above compound 18 was produced by the same method as the method for producing the compound 1, except that the intermediate a21 was used instead of the intermediate A2. (13 g, yield 43%, MS: [ M + H ]] ⁺ ＝957.3)

Example 1

ITO (indium tin oxide) is added

The glass substrate (corning 7059 glass) coated with a thin film was put in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent used was a product of fisher (fischer co.) and the distilled water used was distilled water filtered twice with a Filter (Filter) manufactured by millipore co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, ultrasonic washing was performed in the order of solvents of isopropyl alcohol, acetone, and methanol, and then dried. On the ITO transparent electrode thus prepared, hexanitrile hexaazatriphenylene (HAT-CN) was added

The hole injection layer is formed by thermal vacuum deposition to a thickness of (3). On the hole injection layer, the following HT1 compound which transports holes was vacuum-evaporated, and then the following HT2 compound was evaporated to form a first

And a second hole transport layer

Next, on the second hole transport layer, the following H1 compound and compound 1 were vacuum-evaporated to form a light emitting layer so that compound 1 was contained in an amount of 3 parts by weight based on 100 parts by weight of the total of the following H1 compound and compound 1

Then, thermal vacuum evaporation was performed in order using the following E0 compound as an electron injection and transport layer

On the above electron transporting and injecting layer, lithium fluoride (LiF) is sequentially added to

Thickness of aluminum and

the cathode was formed by vapor deposition to a certain thickness, and then an organic light-emitting device was manufactured. In the above process, the evaporation speed of the organic material is maintained

Maintenance of deposition rate of LiF

Maintenance of aluminum vapor deposition rate

To

Examples 2 to 12

Organic light-emitting devices of examples 2 to 12 were produced in the same manner as in example 1, except that compounds listed in table 1 below were used as phosphorescent dopants in the formation of the light-emitting layer instead of compound 1.

Comparative examples 1 to 3

Organic light-emitting devices of comparative examples 1 to 3 were each produced in the same manner as in example 1, except that compounds described in table 1 below were used instead of compound 1 as a phosphorescent dopant in forming a light-emitting layer.

The organic light-emitting devices fabricated in examples 1 to 12 and comparative examples 1 to 3 were measured for voltage, efficiency, color coordinates, and lifetime by applying current thereto, and the results are shown in table 1 below.

T95 represents the time required for the luminance to decrease from the initial luminance to 95%. Lambda _max Indicates the maximum luminescence wavelength.

[ TABLE 1]

From the results of table 1 above, it is understood that the organic light emitting device using the compound of the present invention exhibits high-purity red light emission, has low voltage, high efficiency, and long life characteristics. The LUMO energy levels of the compounds of the present invention are distributed mainly in the ring of pyridazine, pyrimidine or pyrazine etc. containing the main ligand. The main ligand of the compound of the present invention comprises more than one electronegative nitrogen atom on the pyridine ringAnd thus a low LUMO rating compared to a compound in which the primary ligand comprises pyridine. Since the energy band gap is narrowed when the LUMO level of the dopant compound is lowered, red light in a long wavelength region can be emitted. As a result, of examples 1 to 12 and comparative examples 1 to 3 using the compound of the present invention

The dopants of the oxazolopyridine, thiazolopyridine, and thienopyrimidine structures exhibit a maximum emission wavelength in a long wavelength region, as compared with each other. In addition, a red wavelength exhibiting excellent color purity, while exhibiting high efficiency and long lifetime. In the case of example 6, the lifetime was increased by about 2 times at most as compared with comparative example 1, and the low driving voltage and high efficiency were maintained.

Claims

1. A compound represented by the following chemical formula 1:

chemical formula 1

In the chemical formula 1, the first and second organic solvents,

adjacent 2 of Y1 to Y4 are carbon atoms to which two "+" of the following chemical formula D are bonded respectively, one of two of Y1 to Y4 which are not bonded is N, and the other is CR1,

chemical formula D

In the chemical formula D, the compound represented by the formula D,

x is O or S, and X is O or S,

r1 to R2, rx, ry and Rz, equal to or different from each other, are each independently hydrogen, deuterium or an alkyl group of 1 to 10 carbon atoms,

r3 is each independently hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms, or is bonded to an adjacent group to form a benzene ring which is unsubstituted or substituted with one or more substituents selected from deuterium or an alkyl group having 1 to 10 carbon atoms,

a is an integer of 0 to 4, and when a is 2 or more, a plurality of R3 s may be the same or different from each other.

2. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulae 1-1 to 1-4:

chemical formula 1-1

Chemical formula 1-2

Chemical formulas 1 to 3

Chemical formulas 1 to 4

In the chemical formula 1-1,

adjacent 2 of Y2 to Y4 are carbon atoms bonded to two "+" of said chemical formula D, respectively, one of Y2 to Y4 not bonded to the "+" of said chemical formula D is CR1,

in the chemical formula 1-2, the,

y3 and Y4 are each a carbon atom bonded to each of two ". DELTA.s" of said formula D, Y1 is CR1,

in the chemical formulae 1 to 3,

y1 and Y2 are each a carbon atom bonded to each of two "-" groups of said formula D, Y4 is CR1,

in the chemical formulae 1 to 4,

adjacent 2 of Y1 to Y3 are carbon atoms to which two "+" of the chemical formula D are bonded respectively, one of Y1 to Y3 not bonded to the "+" of the chemical formula D is CR1,

r1 is hydrogen;

r3, rx, ry, rz and a are as defined in chemical formula 1.

3. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 2-1 or chemical formula 2-2:

chemical formula 2-1

Chemical formula 2-2

In the chemical formula 2-1 and the chemical formula 2-2,

one of Y1 and Y2 is N, and the other is CR1,

x, R1 to R3, rx, ry, rz and a are as defined in chemical formula 1.

4. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 3-1 or chemical formula 3-2:

chemical formula 3-1

Chemical formula 3-2

In the chemical formula 3-1 and the chemical formula 3-2,

one of Y1 and Y4 is N and the other is CR1,

x, R1 to R3, rx, ry, rz and a are as defined in chemical formula 1.

5. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 4-1 or chemical formula 4-2:

chemical formula 4-1

Chemical formula 4-2

In the chemical formula 4-1 and the chemical formula 4-2,

one of Y3 and Y4 is N and the other is CR1,

x, R1 to R3, rx, ry, rz and a are as defined in chemical formula 1.

6. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 5:

chemical formula 5

In the chemical formula 5, the first and second organic solvents,

y1 to Y4, rx, ry and Rz are as defined in chemical formula 1,

r4 is deuterium or alkyl group having 1 to 10 carbon atoms,

7. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the group consisting of:

8. an organic light emitting device, comprising: a first electrode, a second electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein the compound according to any one of claims 1 to 7 is contained in one or more of the one or more organic layers.

9. The organic light emitting device according to claim 8, wherein the compound represented by chemical formula 1 is contained in one or more layers of one or more light emitting layers.

10. The organic light emitting device according to claim 9, wherein the light emitting layer including the compound represented by chemical formula 1 is a red light emitting layer.

11. The organic light emitting device according to claim 8, wherein the compound represented by chemical formula 1 is contained in one or more layers of a hole injection layer, a hole transport layer, a layer simultaneously performing hole injection and transport, and a hole adjusting layer.

12. The organic light emitting device according to claim 8, wherein the compound represented by chemical formula 1 is contained in one or more layers of an electron injection layer, an electron transport layer, a layer in which electron injection and transport are simultaneously performed, and an electron adjustment layer.