CN109476678B - Heterocyclic compound and organic light-emitting element comprising same - Google Patents

Abstract

The present specification relates to a heterocyclic compound represented by chemical formula 1 and an organic light emitting element including the same.

Description

Heterocyclic compound and organic light-emitting element comprising same

Technical Field

The present application claims priority to korean patent application No. 10-2017-0019961, filed on 14.2.2017 from the korean patent office, the contents of which are incorporated herein in their entirety.

The present specification relates to a heterocyclic compound and an organic light-emitting element including the same.

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 element utilizing an organic light emitting phenomenon generally has a structure including an anode and a cathode with an organic layer interposed therebetween. In order to improve the efficiency and stability of the organic light-emitting device, the organic layer is often composed of a multilayer structure composed of different materials, and the multilayer structure may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In the structure of such an organic light emitting element, if a voltage is applied between the electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, excitons (exiton) are formed when the injected holes and electrons meet each other, and light is emitted when the excitons are transitioned to the ground state again.

There is a continuing need to develop new materials for the above-described organic light emitting elements.

Disclosure of Invention

The present specification provides a heterocyclic compound and an organic light-emitting element including the same.

According to one embodiment of the present specification, there is provided a heterocyclic compound represented by the following chemical formula 1.

[ chemical formula 1]

In the chemical formula 1 described above,

x1 is O or S,

l1 is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

y1 and Y3 are N, Y2 is CR13 and Y4 is CR14, or Y2 and Y4 are N, Y1 is CR14 and Y3 is CR13,

r13 represents a group bonded to L1,

r2 and R3, or R3 and R4 are groups bound to the atom of the following chemical formula 2,

the group not bonded to the group of chemical formula 2, R1, R5 to R12 and R14, which are the same or different from each other, of R2 to R4, are each independently hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted ring,

n is 1 or 2, and n is a hydrogen atom,

when n is 2, two L1 are the same as or different from each other,

[ chemical formula 2]

In the chemical formula 2 described above, the,

is a site binding to R2 and R3, or R3 and R4 of the above chemical formula 1,

ar1 is a substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

r15 to R18 are the same as or different from each other, and each is independently hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted ring.

In addition, according to one embodiment of the present specification, there is provided an organic light-emitting element including: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers include a heterocyclic compound represented by the chemical formula 1.

The heterocyclic compound according to one embodiment of the present specification can be used as a material for an organic layer of an organic light-emitting element, and by using the heterocyclic compound, improvement in efficiency, lower driving voltage, and/or improvement in lifetime characteristics can be achieved in the organic light-emitting element.

Drawings

Fig. 1 illustrates an organic light emitting element 10 according to an embodiment of the present description.

Fig. 2 illustrates an organic light emitting element 11 according to another embodiment of the present specification.

FIG. 3 is a mass spectrum of Compound 1 produced in Synthesis example 1 of the present specification.

FIG. 4 is a mass spectrum of Compound 2 produced in Synthesis example 2 of the present specification.

FIG. 5 is a mass spectrum of Compound 3 produced in Synthesis example 3 of the present specification.

FIG. 6 is a mass spectrum of Compound 4 produced in Synthesis example 4 of the present specification.

FIG. 7 is a mass spectrum of Compound 5 produced in Synthesis example 5 of the present specification.

FIG. 8 is a mass spectrum of Compound 6 produced in Synthesis example 6 of the present specification.

FIG. 9 is a mass spectrum of Compound 7 produced in Synthesis example 7 of the present specification.

FIG. 10 is a mass spectrum of Compound 8 produced in Synthesis example 8 of the present specification.

FIG. 11 is a mass spectrum of Compound 9 produced in Synthesis example 9 of the present specification.

FIG. 12 is a mass spectrum of Compound 10 produced in Synthesis example 10 of the present specification.

FIG. 13 is a mass spectrum of Compound 11 produced in Synthesis example 11 of the present specification.

FIG. 14 is a mass spectrum of Compound 12 produced in Synthesis example 12 of the present specification.

FIG. 15 is a mass spectrum of Compound 13 produced in Synthesis example 13 of the present specification.

FIG. 16 is a mass spectrum of Compound 14 produced in Synthesis example 14 of the present specification.

FIG. 17 is a mass spectrum of Compound 15 produced in Synthesis example 15 of the present specification.

FIG. 18 is a mass spectrum of Compound 16 produced in Synthesis example 16 of the present specification.

FIG. 19 is a mass spectrum of Compound 17 produced in Synthesis example 17 of the present specification.

FIG. 20 is a mass spectrum of Compound 18 produced in Synthesis example 18 of the present specification.

FIG. 21 is a mass spectrum of Compound 19 produced in Synthesis example 19 of the present specification.

FIG. 22 is a mass spectrum of Compound 20 produced in Synthesis example 20 of the present specification.

Fig. 23 is a mass spectrum of compound 21 produced in synthesis example 21 of the present specification.

FIG. 24 is a mass spectrum of Compound 22 produced in Synthesis example 22 herein.

FIG. 25 is a mass spectrum of Compound 23 produced in Synthesis example 23 of the present specification.

FIG. 26 is a mass spectrum of Compound 24 produced in Synthesis example 24 of the present specification.

Description of the symbols

10. 11: organic light emitting element

20: substrate

30: a first electrode

40: luminescent layer

50: second electrode

60: hole injection layer

70: hole transport layer

80: electron transport layer

90: electron injection layer

Detailed Description

The present specification will be described in more detail below.

The present specification provides heterocyclic compounds represented by the above chemical formula 1.

The heterocyclic compound represented by the above chemical formula 1 according to one embodiment of the present description has a structure in which the 2-position of benzofuran [3,4-d ] pyrimidine, benzofuran [2,3-d ] pyrimidine, benzothieno [3,4-d ] pyrimidine, or benzothieno [2,3-d ] pyrimidine is bonded to N of indolocarbazole through L1, and thus the flow of electrons is smooth, and the above chemical formula 2 is bonded to R2 and R3, or R3 and R4 in the above chemical formula 1, and thus the steric hindrance (steric hindrance) of the above chemical formula 1 is reduced and the structure is stabilized, so that the organic light-emitting element including the above chemical formula 1 has a low driving voltage, excellent efficiency, and a long lifetime.

In the present specification, when a part is referred to as "including" a certain component, unless specifically stated to the contrary, it means that the other component may be further included, and the other component is not excluded.

In the present specification, when a member is referred to as being "on" another member, it includes not only a case where the member is in contact with the another member but also a case where the another member is present between the two members.

Examples of the substituent in the present specification will be described below, but the present invention is not limited thereto.

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

The term "substituted or unsubstituted" in the present specification means substituted or unsubstituted with one or more groups selected from deuterium, a halogen group, a nitrile group, a nitro group, an imide group, an amide group, a carbonyl group, an ester group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group(s) ((s))

Alkyl thioaxy), substituted or unsubstituted arylthio(s) ((R)

Aryl thio), substituted or unsubstituted alkyl sulfoxide group(s) ((s)

Alkyl sulfoxy), a substituted or unsubstituted arylsulfoxide group(s) ((s)

Aryl sufoxy), substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boryl, substituted or unsubstituted amino, substituted or unsubstituted Aryl phosphino, substituted or unsubstituted phosphinoxide, substituted or unsubstituted Aryl, and substituted or unsubstituted heterocyclic group, or substituted with a substituent in which 2 or more substituents among the above-exemplified substituents are linked, or does not have any substituent. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. Namely, biphenyl groupIt may be an aryl group or a substituent in which 2 phenyl groups are bonded.

In the context of the present specification,

refers to a site that binds to other substituents or binding sites.

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

In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 30. Specifically, the compound may have the following structure, but is not limited thereto.

In the present specification, with respect to the amide group, the nitrogen of the amide group may be substituted with hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 30. Specifically, the compound may have the following structure, but is not limited thereto.

In the present specification, with respect to the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples thereof include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methylbutyl group, 1-ethylbutyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2-dimethylheptyl group, 1-ethylpropyl group, 1-dimethylpropyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, specifically, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2, 3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2, 3-dimethylcyclohexyl group, a 3,4, 5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but is not limited thereto.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but the number of carbon atoms is preferably 1 to 30. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc., but is not limited thereto.

In the present specification, the amine group may be selected from-NH₂Alkylamino, N-alkylarylamino, arylamino, N-arylheteroarylamino, N-alkylheteroarylamino and heteroarylamino groups having no particular number of carbon atomsBut are not limited to, but are preferably 1 to 30. Specific examples of the amine group include, but are not limited to, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a 9-methylanthrylamino group, a diphenylamino group, an N-phenylnaphthylamino group, a ditolylamino group, an N-phenyltolylamino group, a triphenylamino group, an N-phenylbiphenylamino group, an N-phenylnaphthylamino group, an N-biphenylnaphthylamino group, an N-naphthylfluorenylamino group, an N-phenylphenanthrylamino group, an N-biphenylphenanthrylamino group, an N-phenylfluorenylamino group, an N-phenylterphenylamino group, an N-phenanthrenylfluorenylamino group, and an N-biphenylfluorenylamino group.

In the present specification, the N-alkylarylamino group means an amino group in which an alkyl group and an aryl group are substituted on N of the amino group.

In the present specification, the N-arylheteroarylamino group means an amino group in which an aryl group and a heteroaryl group are substituted on the N of the amino group.

In the present specification, the N-alkylheteroarylamino group means an amino group in which an alkyl group and a heteroaryl group are substituted on N of the amino group.

In the present specification, alkylamino group, N-arylalkylamino group, alkylthio group: (

Alkyl thio xy), Alkyl sulfoxide group(s) ((II)

Alkyl groups in Alkyl sulfoxy) and N-alkylheteroarylamino groups are the same as those exemplified above for Alkyl groups. Specifically, examples of the alkylthio group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group, and an octylthio group, and examples of the alkylsulfinyl group include a methylsulfonyl group

Ethyl sulfoxide group, propyl sulfoxide group, butyl sulfoxide group, etc., but are not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (diphenylen-1-yl) ethen-1-yl, stilbenyl, and styryl.

In the present specification, 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 this specification, the boron group may be-BR₁₀₀R₁₀₁R is as defined above₁₀₀And R₁₀₁The same or different from each other, may be each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group of carbon number 3 to 30, a substituted or unsubstituted linear or branched alkyl group of carbon number 1 to 30, a substituted or unsubstituted monocyclic or polycyclic aryl group of carbon number 6 to 30, and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group of carbon number 2 to 30.

In the present specification, specific examples of the phosphine oxide group include a diphenylphosphine oxide group, a dinaphthylphosphine oxide group and the like, but the phosphine oxide group is not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30. Specifically, asPolycyclic aromatic groups selected from naphthyl, anthryl, phenanthryl, triphenyl, pyrenyl, phenalenyl, perylenyl, perylene, and the like,

And a fluorenyl group, but the present invention is not limited thereto.

In the present specification, the above-mentioned fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.

When the above-mentioned fluorenyl group is substituted, it may be

And

and the like. But is not limited thereto.

In the present specification, an "adjacent" group means a substituent substituted on an atom directly connected to an atom substituted with the substituent, a substituent closest to the substituent in terms of a steric structure, or another substituent substituted on an atom substituted with the substituent. For example, 2 substituents substituted at 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.

In the present specification, the aryl group in the aryloxy group, the arylthio group, the arylsulfoxide group, the N-arylalkylamino group, the N-arylheteroarylamino group, and the arylphosphine group is exemplified by the aryl group described above. Specifically, the aryloxy group includes, but is not limited to, phenoxy, p-tolyloxy, m-tolyloxy, 3, 5-dimethyl-phenoxy, 2,4, 6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthracenyloxy, 2-anthracenyloxy, 9-anthracenyloxy, 1-phenanthrenyloxy, 3-phenanthrenyloxy, 9-phenanthrenyloxy, etc., and the arylthio group includes phenylthio, 2-methylphenylthio, 4-tert-butylphenylthio, etc., and the arylsulfoxido group includes phenylsulfoxido, p-methylsulfonimido, etc.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing 2 or more aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or both a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamine group can be selected from the examples of the aryl group described above.

In the present specification, the heteroaryl group contains 1 or more heteroatoms other than carbon atoms, and specifically, the above-mentioned heteroatoms may contain 1 or more atoms selected from O, N, Se, S and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,

Azolyl group,

Oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl

Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoquinoyl

Azolyl group,

Examples of the organic solvent include, but are not limited to, an organic solvent such as ethanol, and the like.

In the present specification, as examples of the heteroarylamino group, there are a substituted or unsubstituted monoheteroarylamino group, a substituted or unsubstituted diheteroarylamino group, or a substituted or unsubstituted triheteroarylamino group. The heteroarylamine group described above that contains more than 2 heteroaryl groups may contain a monocyclic heteroaryl group, a polycyclic heteroaryl group, or both a monocyclic heteroaryl group and a polycyclic heteroaryl group. For example, the heteroaryl group in the heteroarylamino group can be selected from the examples of the heteroaryl group described above.

In this specification, examples of the heteroaryl group in the N-arylheteroarylamino group and the N-alkylheteroarylamino group are the same as those of the heteroaryl group described above.

In the present specification, arylene means an aryl group having two binding sites on the aryl group, i.e., a 2-valent group. The above description of aryl groups applies in addition to the 2-valent groups.

In the present specification, heteroarylene means an aryl group having two binding sites on the heteroaryl group, i.e., a 2-valent group. The above description of heteroaryl groups can be applied, except that they are each a 2-valent group.

In the present specification, a substituted or unsubstituted ring formed by bonding adjacent groups to each other, and a "ring" refers to a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

In the present specification, the hydrocarbon ring may be aromatic, aliphatic, or a fused ring of aromatic and aliphatic, and may be selected from the cycloalkyl groups and the aryl groups described above, except that the above is not 1-valent.

In the present specification, the aromatic ring may be a monocyclic ring or a polycyclic ring, and may be selected from the above-mentioned examples of aryl groups except for having a valence of 1.

In the present specification, the heterocyclic ring contains 1 or more hetero atoms other than carbon atoms, and specifically, the hetero atom may contain 1 or more atoms selected from O, N, Se, S, and the like. The heterocyclic ring may be monocyclic or polycyclic, may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from the examples of the heteroaryl group and the heterocyclic group except that it has a valence of 1.

According to an embodiment of the present specification, the chemical formula 1 may be represented by any one of the following chemical formulas 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 formulas 1-1 to 1-4,

x1, L1, n, Y1 to Y4, R1, R2 and R4 to R12 are as defined above in chemical formula 1,

ar1 and R15 to R18 are as defined above for formula 2.

According to an embodiment of the present disclosure, in chemical formula 1, Y1 and Y3 are N, Y2 is CR13, and Y4 is CR 14.

According to an embodiment of the present disclosure, in chemical formula 1, Y2 and Y4 are N, Y1 is CR14, and Y3 is CR 13.

According to an embodiment of the present disclosure, R13 is a group bonded to L1.

According to an embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 1-5 to 1-12.

[ chemical formulas 1 to 5]

[ chemical formulas 1 to 6]

[ chemical formulas 1 to 7]

[ chemical formulas 1 to 8]

[ chemical formulas 1 to 9]

[ chemical formulas 1-10]

[ chemical formula-11 ]

[ chemical formulas 1 to 12]

In the above chemical formulas 1-5 to 1-12,

x1, L1, n, R1, R2, R4 to R12 and R14 are as defined above,

ar1 and R15 to R18 are as defined above for formula 2.

According to an embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 1-13 to 1-20.

[ chemical formulas 1 to 13]

[ chemical formulas 1 to 14]

[ chemical formulas 1 to 15]

[ chemical formulas 1 to 16]

[ chemical formulas 1 to 17]

[ chemical formulas 1 to 18]

[ chemical formulas 1 to 19]

[ chemical formulas 1 to 20]

In the above chemical formulas 1-13 to 1-20,

l1, n, R1, R2, R4 to R12 and R14 are as defined above,

ar1 and R15 to R18 are as defined above for formula 2.

According to an embodiment of the present specification, the above chemical formula 1 is represented by any one of the following chemical formulas 1-21 to 1-28.

[ chemical formulas 1 to 21]

[ chemical formulas 1 to 22]

[ chemical formulas 1 to 23]

[ chemical formulas 1 to 24]

[ chemical formulas 1 to 25]

[ chemical formulas 1 to 26]

[ chemical formulas 1 to 27]

[ chemical formulas 1 to 28]

In the above chemical formulas 1-21 to 1-28,

l1, n, R1, R2, R4 to R12 and R14 are as defined above,

ar1 and R15 to R18 are as defined above for formula 2.

According to an embodiment of the present disclosure, R14 is a substituted or unsubstituted aryl group.

According to an embodiment of the present disclosure, R14 is an aryl group.

According to an embodiment of the present disclosure, R14 is phenyl or naphthyl.

According to an embodiment of the present specification, Ar1 represents an aryl group or a heteroaryl group substituted or unsubstituted with an aryl group.

According to one embodiment of the present specification, Ar1 is a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a fluoranthenyl group, a triphenylene group, a pyrenyl group, a pyridyl group, a pyrimidyl group, a triazinyl group substituted with an aryl group, or a quinazolinyl group substituted or unsubstituted with an aryl group.

According to one embodiment of the present specification, Ar1 is a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a fluoranthenyl group, a triphenylene group, a pyrenyl group, a pyridyl group, a pyrimidyl group, a triazinyl group substituted with a phenyl group, or a quinazolinyl group substituted or unsubstituted with a phenyl group or a naphthyl group.

According to an embodiment of the present disclosure, the chemical formula 1 may be selected from the following compounds.

According to one embodiment of the present specification, there is provided an organic light-emitting element including: the organic light-emitting device includes a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include the heterocyclic compound.

According to one embodiment of the present description, the organic layer of the organic light-emitting device of the present description may be formed of a single layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light-emitting element of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting element is not limited thereto, and fewer or more organic layers may be included.

For example, the structure of the organic light-emitting element in the present specification may have the structure shown in fig. 1 and 2, but is not limited thereto.

Fig. 1 illustrates a structure of an organic light emitting element 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20. Fig. 1 illustrates an exemplary structure of an organic light emitting device according to an embodiment of the present disclosure, and may further include another organic layer.

Fig. 2 illustrates a structure of an organic light emitting element in which a first electrode 30, a hole injection layer 60, a hole transport layer 70, a light emitting layer 40, an electron transport layer 80, an electron injection layer 90, and a second electrode 50 are sequentially stacked on a substrate 20. Fig. 2 shows an exemplary structure of the embodiment of the present specification, and may further include another organic layer.

According to one embodiment of the present disclosure, the organic layer includes a hole transport layer, and the hole transport layer includes a heterocyclic compound represented by the chemical formula 1.

According to one embodiment of the present disclosure, the organic layer includes an electron transport layer, an electron injection layer, or a layer that transports and injects electrons at the same time, and the electron transport layer, the electron injection layer, or the layer that transports and injects electrons at the same time includes the heterocyclic compound.

According to one embodiment of the present disclosure, the organic layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by the chemical formula 1.

According to one embodiment of the present disclosure, the organic layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by the chemical formula 1 as a host material of the light emitting layer.

In one embodiment of the present specification, the organic layer includes a heterocyclic compound represented by the chemical formula 1 as a host material, and may include other organic compounds, metals, or metal compounds as a dopant.

The dopant may be 1 or more selected from the following exemplified compounds, but is not limited thereto.

According to an embodiment of the present disclosure, the organic layer may further include 1 or more layers selected from a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

In the organic light-emitting element of the present specification, 1 or more of the organic layers may be produced using a material and a method known in the art, except that the heterocyclic compound of the present specification, that is, the heterocyclic compound represented by the above chemical formula 1 is included.

When the organic light emitting element 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 element in this specification can be manufactured by stacking a first electrode, an organic layer, and a second electrode in this order on a substrate. In this case, the following method can be used: a first electrode is formed by depositing metal, a metal oxide having conductivity, 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, an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the first electrode, and a substance which can be used as a second electrode is deposited on the organic layer. In addition to the above method, the second electrode material, the organic layer, and the first electrode material may be sequentially deposited on the substrate to manufacture the organic light-emitting element. In addition, regarding the heterocyclic compound represented by the above chemical formula 1, in the manufacture of the organic light emitting element, the organic layer may be formed not only by a vacuum evaporation method but also by a solution coating method. 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.

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

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

The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. As specific examples of the anode material which can be used in the present invention, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), and the like; such as ZnO, Al or SnO₂A combination of a metal such as Sb and an oxide; such as 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. As specific examples of the cathode material, there are magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin andmetals such as lead or alloys thereof; such as LiF/Al or LiO₂Multilayer structure materials such as/Al, Mg/Ag, etc., but not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: has an ability to transport holes, has a hole injection effect from the anode, has an excellent hole injection effect with respect to 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 species is between the work function of the anode species 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, and the hole transport material is a material that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.

The electron blocking layer is a layer which prevents electrons injected from the electron injection layer from entering the hole injection layer through the light-emitting layer, and can improve the life and efficiency of the element.

The light-emitting substance of the light-emitting layer 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 a substance having a high quantum efficiency with respect to fluorescence or phosphorescence is preferable. 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 includes aromatic fused ring derivatives, heterocyclic compounds, and the like. Specifically, the aromatic condensed 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 carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds

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

As the dopant material, there are aromatic amine derivatives, styryl amine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, or the like having an arylamine group,

Diindenoperene (Periflanthene) and the like, as the styrene amine compound, a compound in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and which is substituted or unsubstituted with 1 or 2 or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.

The hole-blocking layer is a layer that prevents holes injected from the hole-injecting layer from entering the electron-injecting layer through the light-emitting layer, and can improve the life and efficiency of the element.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and the electron transport layer is a substance that can favorably receive electrons from the cathode and transfer the electrons to the light-emitting layer, and a substance having a large electron mobility is suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq₃The complex of (3), the organic radical compound, the hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. In particular, examples of suitable cathode substances are the usual substances having a low work function and associated with an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium are present, for each, along with an aluminum or silver layer.

The electron injection layer is a layer for injecting electrons from the electrode, and is preferably a compound of: has an ability to transport electrons, an electron injection effect from a cathode, an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and is excellent in thin film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane (Anthraquinodimethane), diphenoquinone, thiopyran dioxide, and,

Oxazole, two

Examples of the nitrogen-containing five-membered ring include, but are not limited to, oxazoles, triazoles, imidazoles, perylene tetracarboxylic acids, fluorenylidene methanes, anthrones, and derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.

Examples of the metal complexes include 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), 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 element of the present specification may be a top emission type, a bottom emission type, or a bidirectional emission type depending on a material used.

According to an embodiment of the present specification, the heterocyclic compound represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting element.

Examples

Hereinafter, the present specification will be described in detail with reference to examples. However, the embodiments according to the present description may be modified into various other forms, and the scope of the present description should not be construed as being limited to the embodiments described in detail below. The embodiments of the present description are provided to more fully describe the present description to those skilled in the art.

The heterocyclic compound according to one embodiment of the present specification can be produced by the basic synthesis process (scheme) of the following reaction formulae 1 to 8, but is not limited thereto.

[ reaction formula 1]

[ reaction formula 2]

[ reaction formula 3]

[ reaction formula 4]

[ reaction formula 5]

[ reaction formula 6]

[ reaction formula 7]

[ reaction formula 8]

In the above reaction formulae 1 to 8, X1, R14, L1 and n are defined as in the above chemical formula 1, and Ar1 is defined as in the above chemical formula 2.

According to one embodiment of the present specification, the intermediates a-1 and a-2 can be produced by the following reaction formulae 9 and 10, but are not limited thereto.

[ reaction formula 9]

[ reaction formula 10]

In the above reaction formulae 9 and 10, X1 and R14 are defined as in the above chemical formula 1.

PREPARATION EXAMPLE 1 Synthesis of Compound A-1-1

In a round-bottom flask, 2, 4-dichlorobenzo [4,5]]Thieno [3,4-d]Pyrimidine (10g,0.04mol), phenylboronic acid (4.8g,0.04mol), calcium carbonate (8.3g,0.06mol), and Pd (PPh)₃)₄(1.8g,4 mol%) was dissolved in anhydrous tetrahydrofuran and water, and the mixture was refluxed at 80 ℃ for 4 hours. After the reaction, the temperature of the reaction product was cooled to room temperature, and the reaction product was extracted with chloroform. The extracted organic layer was dehydrated over anhydrous magnesium sulfate and recrystallized from Ethyl acetate (Ethyl acetate) to obtain compound a-1-1(9.53g, 82%).

PREPARATION EXAMPLE 2 Synthesis of Compound A-1-2

Compound A-1-2 was obtained in the same manner as in production example 1 except that 1-naphthylboronic acid was used instead of phenylboronic acid.

PREPARATION EXAMPLE 3 Synthesis of Compound A-1-3

Compound A-1-3 was obtained in the same manner as in production example 1 except that 2-naphthylboronic acid was used instead of phenylboronic acid.

PREPARATION EXAMPLE 4 Synthesis of Compound A-1-4

Compound A-1-4 was obtained in the same manner as in production example 1 except that [1,1' -biphenyl ] -4-ylboronic acid was used in place of phenylboronic acid.

PREPARATION EXAMPLE 5 Synthesis of Compound A-2-1

Compound A-2-1 was obtained in the same manner as in preparation example 1 except that 2, 4-dichlorobenzofuran [3,2-d ] pyrimidine was used in place of 2, 4-dichlorobenzo [4,5] thieno [3,4-d ] pyrimidine.

PREPARATION EXAMPLE 6 Synthesis of Compound A-2-2

Compound A-2-2 was obtained in the same manner as in preparation example 1 except that 2, 4-dichlorobenzofuran [3,2-d ] pyrimidine was used in place of 2, 4-dichlorobenzo [4,5] thieno [3,4-d ] pyrimidine and 1-naphthylboronic acid was used in place of phenylboronic acid.

PREPARATION EXAMPLE 7 Synthesis of Compound A-2-3

Compound A-2-3 was obtained in the same manner as in preparation example 1 except that 2, 4-dichlorobenzofuran [3,2-d ] pyrimidine was used in place of 2, 4-dichlorobenzo [4,5] thieno [3,4-d ] pyrimidine and 2-naphthylboronic acid was used in place of phenylboronic acid.

PREPARATION EXAMPLE 8 Synthesis of Compound A-2-4

Compound A-2-4 was obtained in the same manner as in preparation example 1 except that 2, 4-dichlorobenzofuran [3,2-d ] pyrimidine was used in place of 2, 4-dichlorobenzo [4,5] thieno [3,4-d ] pyrimidine and [1,1' -biphenyl ] -4-ylboronic acid was used in place of phenylboronic acid.

PREPARATION EXAMPLE 9 Synthesis of Compound A-3-1

Compound A-3-1 was obtained in the same manner as in production example 1 except that 2, 4-dichlorobenzo [4,5] thieno [2,3-d ] pyrimidine was used in place of 2, 4-dichlorobenzo [4,5] thieno [3,4-d ] pyrimidine.

PREPARATION EXAMPLE 10 Synthesis of Compound A-3-2

Compound A-3-2 was obtained in the same manner as in production example 1 except that 2, 4-dichlorobenzo [4,5] thieno [2,3-d ] pyrimidine was used in place of 2, 4-dichlorobenzo [4,5] thieno [3,4-d ] pyrimidine and 1-naphthylboronic acid was used in place of phenylboronic acid.

PREPARATION EXAMPLE 11 Synthesis of Compound A-3-3

Compound A-3-3 is obtained in the same manner as in production example 1 except that 2, 4-dichlorobenzo [4,5] thieno [2,3-d ] pyrimidine is used in place of 2, 4-dichlorobenzo [4,5] thieno [3,4-d ] pyrimidine and 2-naphthylboronic acid is used in place of phenylboronic acid.

PREPARATION EXAMPLE 12 Synthesis of Compound A-3-4

Compound A-3-4 can be obtained in the same manner as in production example 1 except that 2, 4-dichlorobenzo [4,5] thieno [2,3-d ] pyrimidine is used in place of 2, 4-dichlorobenzo [4,5] thieno [3,4-d ] pyrimidine and [1,1' -biphenyl ] -4-ylboronic acid is used in place of phenylboronic acid.

PREPARATION EXAMPLE 13 Synthesis of Compound A-4-1

Compound A-4-1 was obtained in the same manner as in preparation example 1 except that 2, 4-dichlorobenzofuran [2,3-d ] pyrimidine was used in place of 2, 4-dichlorobenzo [4,5] thieno [3,4-d ] pyrimidine.

PREPARATION EXAMPLE 14 Synthesis of Compound A-4-2

Compound A-4-2 was obtained in the same manner as in preparation example 1 except that 2, 4-dichlorobenzofuran [2,3-d ] pyrimidine was used in place of 2, 4-dichlorobenzo [4,5] thieno [3,4-d ] pyrimidine and 1-naphthylboronic acid was used in place of phenylboronic acid.

PREPARATION EXAMPLE 15 Synthesis of Compound A-4-3

Compound A-4-3 is obtained in the same manner as in production example 1 except that 2, 4-dichlorobenzofuran [2,3-d ] pyrimidine is used instead of 2, 4-dichlorobenzo [4,5] thieno [3,4-d ] pyrimidine, and 2-naphthylboronic acid is used instead of phenylboronic acid.

PREPARATION EXAMPLE 16 Synthesis of Compound A-4-4

Compound A-4-4 was obtained in the same manner as in preparation example 1 except that 2, 4-dichlorobenzofuran [2,3-d ] pyrimidine was used in place of 2, 4-dichlorobenzo [4,5] thieno [3,4-d ] pyrimidine and [1,1' -biphenyl ] -4-ylboronic acid was used in place of phenylboronic acid.

Preparation example 17 Synthesis of Compound B- (a) -1

In a round-bottomed flask, compound A-1-1(10g,0.034mol), 5, 6-indolino [2,3-b ] carbazole (8.6g,0.034mol), potassium phosphate (14.3g,0.067mol) were dissolved in 100ml of N, N-Dimethylacetamide (N, N-Dimethylacetamide), and the mixture was refluxed at 160 ℃ for 1 hour. After the reaction is finished, cooling the temperature to normal temperature, pouring the reactant into water to separate out solid, and filtering. The filtered solid was dissolved in chloroform and extracted. The extracted organic layer was dehydrated over anhydrous magnesium sulfate and recrystallized from Ethyl acetate (Ethyl acetate) to obtain compound B- (a) -1(14.8g, 85%).

Preparation example 18 Synthesis of Compound B- (a) -2

Compound B- (a) -2 was obtained in the same manner as in preparation example 17, except that Compound A-2-2 was used in place of Compound A-1-1.

Preparation example 19 Synthesis of Compound B- (B) -1

Compound B- (B) -1 was obtained in the same manner as in production example 17, except that 5, 11-indolino [3,2-B ] carbazole was used instead of 5, 6-indolino [2,3-B ] carbazole and compound a-3-2 was used instead of compound a-1-1.

Preparation example 20 Synthesis of Compound B- (B) -2

Compound B- (B) -2 was obtained in the same manner as in preparation example 17, except that 5, 11-indolino [3,2-B ] carbazole was used instead of 5, 6-indolino [2,3-B ] carbazole and compound a-4-3 was used instead of compound a-1-1.

Preparation example 21 Synthesis of Compound B- (c) -1

Compound B- (c) -1 was obtained in the same manner as in production example 17, except that 5, 8-indolino [2,3-c ] carbazole was used instead of 5, 6-indolino [2,3-B ] carbazole and compound a-2-2 was used instead of compound a-1-1.

Preparation example 22 Synthesis of Compound B- (c) -2

Compound B- (c) -2 was obtained in the same manner as in production example 17, except that 5, 8-indolino [2,3-c ] carbazole was used instead of 5, 6-indolino [2,3-B ] carbazole and compound a-3-1 was used instead of compound a-1-1.

Preparation example 23 Synthesis of Compound B- (d) -1

Compound B- (d) -1 was obtained in the same manner as in production example 17, except that 5, 12-indolino [3,2-a ] carbazole was used instead of 5, 6-indolino [2,3-B ] carbazole and compound a-1-3 was used instead of compound a-1-1.

Preparation example 24 Synthesis of Compound B- (d) -2

Compound B- (d) -2 was obtained in the same manner as in production example 17, except that 5, 12-indolino [3,2-a ] carbazole was used instead of 5, 6-indolino [2,3-B ] carbazole and compound a-4-1 was used instead of compound a-1-1.

Synthesis example 1 Synthesis of Compound 1

A round-bottomed flask was charged with compound B- (a) -1(10g,0.019mol), 1-bromonaphthalene (4g,0.019mol) and potassium phosphate (8.2g,0.038mol), and bis (tri-tert-butylphosphine) palladium (0.02g,0.2 mol%) was added under reflux for further 4 hours under reflux. After the reaction was completed, the temperature was cooled to normal temperature, and the precipitated solid was filtered. Then, the filtered solid was dissolved in chloroform and extracted. The extracted organic layer was dehydrated over anhydrous magnesium sulfate and recrystallized from Ethyl acetate (Ethyl acetate) to obtain 9.7g (78%) of compound 1 (example 1-2). ([ M + H ] ═ 643)

Fig. 3 is a mass spectrum of compound 1 produced in synthesis example 1.

Synthesis example 2 Synthesis of Compound 2

Compound 2 (examples 1 to 12) was obtained in the same manner as in Synthesis example 1 except that 2-chloropyrimidine was used in place of 1-bromonaphthalene. ([ M + H ] ═ 595)

Fig. 4 is a mass spectrum of compound 2 produced in synthesis example 2.

Synthesis example 3 Synthesis of Compound 3

Compound 3 (examples 1 to 17) was obtained in the same manner as in Synthesis example 1 except that 2-chloro-4, 6-diphenyl-1, 3, 5-triazine was used in place of 1-bromonaphthalene. ([ M + H ] ═ 748)

Fig. 5 is a mass spectrum of compound 3 produced in synthesis example 3.

Synthesis example 4 Synthesis of Compound 4

Compound 4 (examples 1 to 120) was obtained in the same manner as in Synthesis example 1, except that 1-bromobenzene was used in place of 1-bromonaphthalene and that compound B- (a) -2 was used in place of compound B- (a) -1. ([ M + H ] ═ 628)

Fig. 6 is a mass spectrum of compound 4 produced in synthesis example 4.

Synthesis example 5 Synthesis of Compound 5

Compound 5 (examples 1 to 124) was obtained in the same manner as in Synthesis example 1, except that 9-bromophenanthrene was used in place of 1-bromonaphthalene and that compound B- (a) -2 was used in place of compound B- (a) -1. ([ M + H ] ═ 727)

Fig. 7 is a mass spectrum of compound 5 produced in synthesis example 5.

Synthesis example 6 Synthesis of Compound 6

Compound 6 (examples 1 to 134) was obtained in the same manner as in Synthesis example 1, except that 2-chloro-4-phenylquinazoline was used in place of 1-bromonaphthalene and that compound B- (a) -2 was used in place of compound B- (a) -1. ([ M + H ] ═ 755)

Fig. 8 is a mass spectrum of compound 6 produced in synthesis example 6.

Synthesis example 7 Synthesis of Compound 7

Compound 7 (specific examples 2 to 74) ([ M + H ] ═ 768) was obtained in the same manner as in synthesis example 1, except that 3-chlorofluoranthene was used instead of 1-bromonaphthalene and compound B- (B) -1 was used instead of compound B- (a) -1

Fig. 9 is a mass spectrum of compound 7 produced in synthesis example 7.

Synthesis example 8 Synthesis of Compound 8

Compound 8 (examples 2 to 76) was obtained in the same manner as in Synthesis example 1, except that 1-bromopyrene was used in place of 1-bromonaphthalene and that compound B- (B) -1 was used in place of compound B- (a) -1. ([ M + H ] ═ 768)

Fig. 10 is a mass spectrum of compound 8 produced in synthesis example 8.

Synthesis example 9 Synthesis of Compound 9

Compound 9 (examples 2 to 84) was obtained in the same manner as in Synthesis example 1 except that 2-chloro-4- (naphthalen-2-yl) quinazoline was used in place of 1-bromonaphthalene and that compound B- (B) -1 was used in place of compound B- (a) -1. ([ M + H ] ═ 822)

Fig. 11 is a mass spectrum of compound 9 produced in synthesis example 9.

Synthesis example 10 Synthesis of Compound 10

Compound 10 (example 2-188) was obtained in the same manner as in 3-1) except that 1-bromobenzene was used instead of 1-bromonaphthalene and compound B- (B) -2 was used instead of compound B- (a) -1 in synthetic example 1. ([ M + H ] ═ 628)

Fig. 12 is a mass spectrum of compound 10 produced in synthesis example 10.

Synthesis example 11 Synthesis of Compound 11

Compound 11 (examples 2 to 194) was obtained in the same manner as in Synthesis example 1, except that 2-bromotriphenylene was used in place of 1-bromonaphthalene and that compound B- (B) -2 was used in place of compound B- (a) -1. ([ M + H ] ═ 778)

Fig. 13 is a mass spectrum of compound 11 produced in synthesis example 11.

Synthesis example 12 Synthesis of Compound 12

Compound 12 (specific examples 2 to 200) was obtained in the same manner as in Synthesis example 1 except that 4-chloropyrimidine was used in place of 1-bromonaphthalene and that compound B- (B) -2 was used in place of compound B- (a) -1. ([ M + H ] ═ 629)

Fig. 14 is a mass spectrum of compound 12 produced in synthesis example 12.

Synthesis example 13 Synthesis of Compound 13

Compound 13 (examples 3 to 122) was obtained in the same manner as in Synthesis example 1, except that 2-bromonaphthalene was used in place of 1-bromonaphthalene and that compound B- (c) -1 was used in place of compound B- (a) -1. ([ M + H ] ═ 678)

Fig. 15 is a mass spectrum of compound 13 produced in synthesis example 13.

Synthesis example 14 Synthesis of Compound 14

Compound 14 (specific examples 3 to 129) was obtained in the same manner as in Synthesis example 1 except that 3-chloropyridine was used in place of 1-bromonaphthalene and Compound B- (c) -1 was used in place of Compound B- (a) -1. ([ M + H ] ═ 628)

Fig. 16 is a mass spectrum of compound 14 produced in synthesis example 14.

Synthesis example 15 Synthesis of Compound 15

Compound 15 (examples 3 to 133) was obtained in the same manner as in Synthesis example 1 except that 2-chloroquinazoline was used in place of 1-bromonaphthalene and that compound B- (c) -1 was used in place of compound B- (a) -1. ([ M + H ] ═ 679)

Fig. 17 is a mass spectrum of compound 15 produced in synthesis example 15.

Synthesis example 16 Synthesis of Compound 16

Compound 16 (examples 3 to 56) was obtained in the same manner as in Synthesis example 1, except that 9-bromophenanthrene was used in place of 1-bromonaphthalene and that compound B- (c) -2 was used in place of compound B- (a) -1. ([ M + H ] ═ 693)

Fig. 18 is a mass spectrum of compound 16 produced in synthesis example 16.

Synthesis example 17 Synthesis of Compound 17

Compound 17 (examples 3 to 62) was obtained in the same manner as in Synthesis example 1 except that 4-chloropyridine was used in place of 1-bromonaphthalene and Compound B- (c) -2 was used in place of Compound B- (a) -1. ([ M + H ] ═ 595)

Fig. 19 is a mass spectrum of compound 17 produced in synthesis example 17.

Synthesis example 18 Synthesis of Compound 18

Compound 18 (examples 3 to 68) was obtained in the same manner as in Synthesis example 1 except that 2-chloro-4, 6-diphenyl-1, 3, 5-triazine was used in place of 1-bromonaphthalene and Compound B- (c) -2 was used in place of Compound B- (a) -1. ([ M + H ] ═ 749)

Fig. 20 is a mass spectrum of compound 18 produced in synthesis example 18.

Synthesis example 19 Synthesis of Compound 19

Compound 19 (examples 4 to 37) was obtained in the same manner as in Synthesis example 1, except that 2-bromonaphthalene was used in place of 1-bromonaphthalene and that compound B- (d) -1 was used in place of compound B- (a) -1. ([ M + H ] ═ 693)

Fig. 21 is a mass spectrum of compound 19 produced in synthesis example 19.

Synthesis example 20 Synthesis of Compound 20

Compound 20 (examples 4 to 38) was obtained in the same manner as in Synthesis example 1 above, except that 4-bromo-1, 1' -biphenyl was used in place of 1-bromonaphthalene and that compound B- (d) -1 was used in place of compound B- (a) -1. ([ M + H ] ═ 719)

Fig. 22 is a mass spectrum of compound 20 produced in synthesis example 20.

Synthesis example 21 Synthesis of Compound 21

Compound 21 (examples 4 to 49) was obtained in the same manner as in Synthesis example 1 above, except that 2-chloro-4-phenylquinazoline was used in place of 1-bromonaphthalene and Compound B- (d) -1 was used in place of Compound B- (a) -1. ([ M + H ] ═ 772)

Fig. 23 is a mass spectrum of compound 21 produced in synthesis example 21.

Synthesis example 22 Synthesis of Compound 22

Compound 22 (examples 4 to 157) was obtained in the same manner as in Synthesis example 1 above, except that 4-bromo-1, 1' -biphenyl was used in place of 1-bromonaphthalene and Compound B- (d) -2 was used in place of Compound B- (a) -1. ([ M + H ] ═ 654)

Fig. 24 is a mass spectrum of compound 22 produced in synthesis example 22.

Synthesis example 23 Synthesis of Compound 23

Compound 23 (examples 4 to 162) was obtained in the same manner as in Synthesis example 1, except that 2-chloropyridine was used in place of 1-bromonaphthalene and Compound B- (d) -2 was used in place of Compound B- (a) -1. ([ M + H ] ═ 578)

Fig. 25 is a mass spectrum of compound 23 produced in synthesis example 23.

Synthesis example 24 Synthesis of Compound 24

Compound 24 (examples 4 to 165) was obtained in the same manner as in Synthesis example 1, except that 2-chloropyrimidine was used in place of 1-bromonaphthalene and that compound B- (d) -2 was used in place of compound B- (a) -1. ([ M + H ] ═ 579)

Fig. 26 is a mass spectrum of compound 24 produced in synthesis example 24.

< production of organic light-emitting device >

Comparative example 1

Will be provided with

The glass substrate coated with ITO (indium tin oxide) is put in distilled water in which a dispersant is dissolved, and washed by ultrasonic waves. At this time, the detergent was prepared by Fischer Co, and distilled water was filtered 2 times by using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating 2 times with distilled water. After the completion of the distilled water washing, the mixture was ultrasonically washed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.

After the substrate was mounted in the vacuum chamber, the base pressure was set to 1X 10^-6torr, organic materials were sequentially deposited on the ITO, that is, DNTPD described below was used as a hole injection and transport layer

As the hole transporting and electron blocking layer, the following NPB was used

The following CBP, which is generally used as a main material for red phosphorescence in many cases, was used as a main material (95 wt%), and was co-evaporated as a dopant

Dp-6(5 wt%) as described above, and Alq as an electron transport layer₃

LiF is used as the cathode

Al

And film formation is sequentially performed. In the above process, the evaporation speed of the organic material is maintained

Maintenance of LiF

Deposition rate of (3), aluminum maintenance

The deposition rate of (3).

Comparative examples 2 to 8

An organic light-emitting element was produced in the same manner as in comparative example 1, except that the following compounds a to G were used instead of the CBP.

Examples 1 to 24

An organic light-emitting element was produced in the same manner as in comparative example 1, except that the compounds 1 to 24 produced in synthesis examples 1 to 24 were used instead of the CBP.

To the organic light emitting elements fabricated in the above comparative examples 1 to 8 and examples 1 to 24, 10mA/cm was applied²And the driving voltage, current efficiency and life were measured, and T95 represents the time required for the luminance to decrease from the initial luminance to 95%. The results are shown in table 1 below.

[ Table 1]

In table 1, comparative example 1 is an organic light-emitting element using CBP as a conventional light-emitting layer host material, and comparative examples 2 and 3 are organic light-emitting elements using a compound of chemical formula 2 bonded to R1 and R2 of chemical formula 1 as a host material of a light-emitting layer.

In addition, comparative examples 4 and 5 are organic light-emitting elements using a compound in which carbazole is bonded at the Y1 position in chemical formula 1 of the present application, and comparative examples 6 to 8 are organic light-emitting elements using, as a host material of a light-emitting layer, a compound in which a substituted aryl group is bonded at the Y3 position in chemical formula 1 of the present application, instead of indolocarbazole.

The organic light-emitting elements of embodiments 1 to 24 are those in which indolocarbazoles are bonded to the Y2 or Y3 position in chemical formula 1 of the present application, that is, compounds formed by bonding chemical formula 2 to R2 and R3, or R3 and R4 in chemical formula 1 are used as host materials of the light-emitting layer.

It is understood that the heterocyclic compound of chemical formula 1 of the present application has smooth intramolecular electron flow, less steric hindrance, and stable structure, and therefore the organic light-emitting devices of examples 1 to 24 using the same have lower driving voltage, superior efficiency, and longer life than the organic light-emitting devices of comparative examples 1 to 8.

Claims (5)

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

chemical formula 1

In the chemical formula 1, the metal oxide is represented by,

x1 is O or S, and X1 is O or S,

l1 is a direct bond that is,

y1 and Y3 are N, Y2 is CR13 and Y4 is CR14, or Y2 and Y4 are N, Y1 is CR14 and Y3 is CR13,

said R13 is a group binding to said L1, R14 is phenyl or naphthyl,

r2 and R3, or R3 and R4 are groups bound to the atom of the following chemical formula 2,

the group not bonded to x of the following chemical formula 2 among R2 to R4, R1 and R5 to R12 are hydrogen,

n is a number of 1, and n is,

chemical formula 2

In the chemical formula 2, the first and second organic solvents,

is a site binding to R2 and R3, or R3 and R4 of said chemical formula 1,

ar1 is phenyl, biphenyl, naphthyl, phenanthryl, fluoranthenyl, triphenylenyl, pyrenyl, pyridyl, pyrimidyl, triazinyl substituted by phenyl, or quinazolinyl substituted or unsubstituted by phenyl or naphthyl,

r15 to R18 are hydrogen.

2. The heterocyclic 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 formulas 1-1 to 1-4,

x1, L1, n, Y1 to Y4, R1, R2 and R4 to R12 are the same as defined in said chemical formula 1,

ar1 and R15 to R18 are as defined in the chemical formula 2.

3. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulae 1-5 to 1-12:

chemical formulas 1 to 5

Chemical formulas 1 to 6

Chemical formulas 1 to 7

Chemical formulas 1 to 8

Chemical formulas 1 to 9

Chemical formulas 1 to 10

Chemical formulas 1 to 11

Chemical formulas 1 to 12

In the chemical formulas 1-5 to 1-12,

x1, L1, n, R1, R2 and R4 to R12 are the same as defined in said chemical formula 1,

ar1 and R15 to R18 are as defined in the chemical formula 2,

r14 is phenyl or naphthyl.

4. The heterocyclic compound according to claim 1, wherein the compound of formula 1 is selected from the following compounds:

5. an organic light-emitting element comprising: a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the heterocyclic compound according to any one of claims 1 to 4, and wherein the organic layer contains a light-emitting layer containing the heterocyclic compound.

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