CN111051323A

CN111051323A - Compound and organic light emitting device including the same

Info

Publication number: CN111051323A
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: 2020-04-21
Anticipated expiration: 2039-05-14
Also published as: CN111051323B; KR20190130409A; WO2019221445A1; KR102206814B1

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, filed on 14.05.2018, to the korean patent office, the entire contents of which are incorporated herein by reference.

Background

In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy 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 substances, 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, excitons (exitons) are formed when the injected holes and electrons meet, and light is emitted when the excitons are transitioned to the ground state again.

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 bonded to two "+" of the following chemical formula D, respectively, one of two of Y1 to Y4 which are not bonded to "+" of the following chemical formula D is N, and the other one 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, alkoxy, aryloxy, silyl group substituted or unsubstituted with alkyl or aryl, aryl or heteroaryl, or combine with each other with adjacent groups to form a ring substituted or unsubstituted with one or more substituents selected from deuterium, alkyl, alkenyl, alkynyl, halogen group, hydroxyl, alkoxy, aryloxy, silyl group substituted or unsubstituted with alkyl or aryl, aryl and heteroaryl,

a is an integer of 0 to 4, and when a is 2 or more, R3 s may be 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 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.

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 material 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 it is a position at which 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), vinyl group(s) ((R)

vinyl), propenyl, allyl, isopropenyl, butenyl, isobutenyl, n-pentenyl and n-hexenyl, but is not limited thereto. Ethylene radical

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 one embodiment, the alkynyl group has 2 to 20 carbon atoms. 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, an 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 about 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 the present specification, the silyl group may be represented by-SiR₁₁R₁₂R₁₃The above chemical formula (II) represents₁₁To R₁₃Each independently may be hydrogen, alkyl or aryl. In the present specification, an alkylsilyl group means a silyl group substituted with an alkyl group, and an arylsilyl group means a silyl group substituted with an aryl group. The silyl group is specifically represented byMethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited thereto.

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. The monocyclic aryl group includes, but is 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 combined with each other to form a spiro structure.

As the above-mentioned substituted fluorenyl group, there are

And

and the like, but is not limited thereto.

In the present specification, the heteroaryl group is a cyclic group containing at least one 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 heteroaryl group has 2 to 30 carbon atoms. According to another embodiment, the above heteroaryl group 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, isoquinoyl

Azolyl group,

Oxadiazolyl, thiadiazolyl, benzothiazolyl, thiophenyl

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 groups "adjacent" 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. Examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, perylene,

pentacene, fluorene, indene, acenaphthylene, phenylfluorenyl, spirofluorene, etc., but is not limited thereto.

The aliphatic heterocyclic ring is an aliphatic ring containing 1 or more heteroatoms. Examples of the aliphatic heterocyclic ring include ethylene oxide (oxirane), tetrahydrofuran, and 1, 4-bis

Alkanes (1,4-dioxane), pyrrolidine, piperidine, morpholine (morpholine), 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, iso

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

Oxadiazoles, thiadiazoles, dithiazoles, tetrazoles, pyrans, thiopyrans, diazines,

Oxazine, thiazine, II

Alkene, triazine, tetrazine, isoquinoline, quinoline, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, naphthyridine, triazabine, indole, indolizine, benzothiazole, benzo

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 chemical formula 1, adjacent two of the Y1 to Y4 means 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 represents hydrogen or an alkyl group having 1 to 10 carbon atoms.

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

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

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

In one embodiment of the present specification, R3 represents 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 represents hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, or a benzene ring which is bonded to an adjacent group to form a benzene ring substituted or unsubstituted 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 represents 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 represents 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 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 to 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, and one of Y2 to Y4 which is not bonded to said "+" of chemical formula D is N or CR1,

in the above chemical formula 1-2,

y3 and Y4 are each a carbon atom bonded to two "+" of the above 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 two "+" 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, and one of Y1 to Y3 which is not bonded to "+" of the above chemical formula D is N or CR1,

r1, R3, Rx, Ry, Rz and a are as defined in formula 1.

In one embodiment of the chemical formula 1-1, one of Y2 to Y4 that is not bonded to "×" of the chemical formula D is CR 1.

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

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

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

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, 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 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, 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, and 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 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 radical, hydroxyl, alkoxy, aryloxy, silyl substituted or unsubstituted by 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 represents hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, R4 represents 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) formula 1 is represented by 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, which are identical to or different from one another, are 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 may be the same or different from each other.

In one embodiment of the present specification, at least 2 of the 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 may be the same or different and each independently represents 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 represents hydrogen or an alkyl group having 1 to 6 carbon atoms.

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

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 for forming the compound represented by chemical formula 2-1, and the method for 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.

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 are 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 are bonded to each other to form a ring,

g3 and G4, which are the same 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, when b1 is 2 or more, G1 s are the same or different from each other,

b2 is an integer of 0 to 7, and when b2 is 2 or more, G2 s are 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 with 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 are 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 contained 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 regulating 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/light emitting layer/electron modulating 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, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); such as ZnO: al or SnO₂: 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 usually used in order to facilitate the transfer of electrons toThe organic layer is preferably a substance having a small work function. 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 LiO₂And 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 an example, there is an 8-hydroxyquinoline aluminum complex (Alq)₃) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is

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 or a heterocyclic ring-containing compound. Specifically, the aromatic condensed ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocyclic ring-containing compound includes a dibenzofuran derivative and a ladder-type furan compound

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 may be substituted with a substituted or unsubstituted arylamineA compound having at least one arylvinyl group. 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 structure 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 capable of injecting electrons from the cathode and transferring the electrons to the light-emitting layer, and is preferably a substance having a high mobility to electrons. As examples of the above electron transporting substance, there are Al complexes of 8-hydroxyquinoline, Al complexes containing Alq₃The 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 an aluminum layer or a silver layer may be formed on a layer formed of the substance.

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: has electron transporting ability, electron injection effect from cathode, excellent electron injection effect for light-emitting layer or light-emitting material, and prevention of light emissionThe exciton generated in the layer migrates to the hole injection layer or the hole injection material, and the thin film forming ability is excellent. 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 lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.

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-methyloxazolo [4,5-d ]]pyrimidine) (50g, 0.3mol) and (3,5-dimethylphenyl) boronic acid (49g, 0.32mol) were dissolved in 500ml of THF, and 2M aqueous potassium carbonate solution (200ml) was added, followed by addition of tetrakis (triphenylphosphine) palladium (10g, 9mmol), followed by stirring at 70 ℃ for 5 hours. 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 with hexane (hexane) and ethyl acetate (20:1 by volume) then afforded intermediate a1(54g, 82% yield).

(2) Production of intermediate A2

Iridium chloride (30g, 0.1mol) and intermediate A1(54g, 0.26mol) were added to 1500ml of 2-ethoxyethanol (2-ethoxyethanol) and 500ml of distilled water in a round-bottom flask under nitrogen atmosphere, and stirred with heating at 130 ℃ for 24 hours. After cooling to room temperature and filtration, the filtrate was washed with 2L of ethanol, thereby producing compound a2(34.3g, yield 53%) as a solid.

(3) Production of Compound 1

Intermediate A2(34.3g, 0.03mol), acetylacetone (acetylacetatone) (7.5g, 0.75mol), and potassium carbonate (potassiumcarbonate) (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) (50:1 by volume), thereby producing compound 1. (18g, yield 43%, MS: [ M + H ]]⁺＝712.8)

Production example 2: synthesis of Compound 2

The above compound 2 was produced by the same method as the method for producing the compound 1, except that 2,2,6,6-tetramethylheptane-3,5-dione (2,2,6,6-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-mentioned compound 3 was produced by the same method as the method for producing the compound 1, except that 3,7-diethylnonane-4,6-dione (3,7-diethylnonane-4,6-dione) was used in place of acetylacetone (acetylacetazone). (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]Pyrimidine (7-chloro-2-methyloxazolo [4,5-d ]]pyrimidine), the above intermediate a3 was produced by the same method as that for producing compound 1, except that pyrimidine). (56g, yield 90%)

(2) Production of intermediate A4

The above 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 a 1. (31g, yield 48%)

(3) Production of Compound 4

In addition to using intermediate A4 instead of intermediate A2The above compound 4 was produced by the same method as the method for producing the compound 1. (17g, yield 43%, MS: [ M + H ]]⁺＝712.8)

Production example 5: synthesis of Compound 5

Compound 5 was produced by the same method as the method for producing compound 1, except that intermediate a4 was used 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)

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. (13g, yield 49%, MS: [ M + H ]]⁺＝825)

Production example 7: synthesis of Compound 7

(1) Production of intermediate A5

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

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. DissolutionAdding acid clay and MgSO into 300ml chloroform₄After stirring, it was filtered through celite. The filtrate was distilled under reduced pressure, and then purified by column chromatography using hexane and ethyl acetate (25: 1 by volume), thereby producing intermediate a 5. (23g, yield 65%)

(2) Production of intermediate A6

Intermediate A5 was used 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 intermediate a1, except that pyrimidine). (28g, yield 73%)

(3) Production of intermediate A7

The above 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 a 1. (31g, yield 48%)

(4) Production of Compound 7

Compound 7 was produced by the same method as the method for producing compound 1, except that intermediate a7 was used instead of intermediate a 2. (15g, 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 2,2,6,6-tetramethylheptane-3,5-dione was used in place of acetylacetone. (19g, yield 58%, MS: [ M + H ]]⁺＝796.9)

Production example 9: synthesis of Compound 9

Intermediate A7 was used in place of intermediate A2The above compound 9 was produced by the same method as the method for producing the compound 1, except that 3,7-diethylnonane-4,6-dione was used in place of acetylacetone. (10g, yield 48%, MS: [ M + H ]]⁺＝825)

Production example 10: synthesis of Compound 10

(1) Production of intermediate A8

The above intermediate A8 was produced in the same manner as in the production of intermediate a5, except that ethanethioamide was used instead of acetylacetone. (37g, yield 61%)

(2) Production of intermediate A9

Intermediate A8 was used instead of 7-chloro-2-methyl

Azolo [4,5-d]Pyrimidine (7-chloro-2-methyloxazolo [4,5-d ]]pyrimidine), the above intermediate a9 was produced by the same method as that for the production of intermediate a1, except that pyrimidine). (51g, yield 83%)

(3) Production of intermediate A10

The above 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 a 1. (45g, yield 50%)

(4) Production of Compound 10

Compound 10 was produced by the same method as the method for producing compound 1, except that intermediate a10 was used instead of intermediate a 2. (37g, yield 45%, MS: [ M + H ]]⁺＝744.9)

Production example 11: synthesis of Compound 11

Compound preparation by reaction with intermediate A10 instead of intermediate A2 and 2,2,6,6-tetramethylheptane-3,5-dione instead of acetylacetoneCompound 11 was prepared in the same manner as in the above-mentioned Process for preparation of Compound 1. (23g, yield 47%, MS: [ M + H ]]⁺＝829)

Production example 12: synthesis of Compound 12

Compound 12 was produced in the same manner as in the production of compound 1, except that intermediate a10 was used instead of intermediate a2 and 3,7-diethylnonane-4,6-dione was used instead of acetylacetone. (28g, 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 in the same manner as in the production of the intermediate a5, except that 2,3-dibromo-5-chloropyrazine (2,3-dibromo-5-chloropyrazine) was used in place of 3, 4-dibromo-6-chloropyridazine. (40g, yield 63%)

(2) Production of intermediate A12

Intermediate A11 was used instead of 7-chloro-2-methyl

Azolo [4,5-d]Pyrimidine (7-chloro-2-methyloxazolo [4,5-d ]]pyrimidine), the above intermediate a12 was produced by the same method as that for the production of intermediate a1, except that pyrimidine). (56g, 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 a 1. (33g, yield 46%)

(4) Production of Compound 13

Was produced by the same method as the method for producing compound 1, except that intermediate a13 was used instead of intermediate a2The above compound 13 is obtained. (25g, yield 41%, MS: [ M + H ]]⁺＝712.8)

Production example 14: synthesis of Compound 14

Compound 14 was produced by the same method as the method for producing compound 1, except that intermediate a13 was used 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)

Production example 15: synthesis of Compound 15

The above compound 15 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 3,7-diethylnonane-4,6-dione was used in place of acetylacetone. (13g, yield 45%, MS: [ M + H ]]⁺＝825)

Production example 16: synthesis of Compound 16

(1) Production of intermediate A16

Intermediate A5 was used 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 that for the production of intermediate a1, except that 2-naphthoic acid (naphthalen-2-ylboronic acid) was used instead of (3,5-dimethylphenyl) boronic acid. (36g, yield 88%)

(3) Production of intermediate A17

The above 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 a 1. (18g, 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 2,2,6,6-tetramethylheptane-3,5-dione was used in place of acetylacetone. (11g, yield 42%, MS: [ M + H ]]⁺＝897)

Production example 17: synthesis of Compound 17

(1) Production of intermediate A18

Intermediate A5 was used 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. (42g, 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 a 1. (22g, yield 51%)

(4) Production of Compound 17

Compound 17 was produced by the same method as the method for producing compound 1, except that intermediate a19 was used instead of intermediate a2 and 2,2,6,6-tetramethylheptane-3,5-dione was used instead of acetylacetone. (15g, 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-methylthiazolidio [4,5-d ]]pyrimidine) (30g, 0.16mol) in place of 7-chloro-2-methyl

Azolo [4,5-d]The above intermediate a20 was produced in the same manner as in the production of the intermediate a1, except that (4- (tert-butyl) naphthalen-2-yl) boronic acid was used instead of (3,5-dimethylphenyl) boronic acid in place of pyrimidine. (39g, yield 72%)

(3) Production of intermediate A21

The above 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 a 1. (24g, yield 50%)

(4) Preparation of Compound 18

Compound 18 was produced by the same method as the method for producing compound 1, except that intermediate a21 was used instead of intermediate a 2. (13g, 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

Is subjected to thermal vacuum deposition toA hole injection layer is formed. 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 hole injection layer

And a second hole transport layer

Next, on the second hole transport layer, a light emitting layer was formed by vacuum vapor deposition of the following H1 compound and the compound 1 so that the 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 the compound 1

. Then, thermal vacuum evaporation was performed in this 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 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 [ alpha ]_maxIndicating 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 mainly distributed in the ring of pyridazine, pyrimidine, pyrazine or the like containing the main ligand. The main ligand of the compound of the present invention has a structure in which one or more nitrogen atoms having a large electronegativity are further contained in the pyridine ring, and thus the LUMO level is low as compared with a compound in which the main ligand contains pyridine. Due to LUMO grading of dopant compoundsWhen the band gap is reduced, and thus 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,

chemical formula D

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

x is O, S, Se, S (═ O), NRm or CRmRn,

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,

in the chemical formula 1-2,

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

in the chemical formulae 1 to 3,

y1 and Y2 are each a carbon atom bound to two ". DELTA.s" of said formula D, Y4 is N or CR1,

in the chemical formulae 1 to 4,

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

r1, R3, Rx, Ry, Rz and a are as defined in 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, the other is N or 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, the other is N or 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, the other is N or 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,

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 among one or more light emitting layers.

10. The organic light emitting device according to claim 9, wherein the light emitting layer comprising 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.